Article No : o28_o01

Weed Control, 2. Individual Herbicides

FRANZ MULLER, (formerly Novartis Crop Protection, Basel), Hergiswil/NW,
Switzerland
ARNOLD P. APPLEBYKI, Oregon State University, Corvallis 973313002, United States

1. Properties of Herbicides . . . . . . . . . . . . . . 209 2.2. Sulfonylureas . . . . . . . . . . . . . . . . . . . . . . . 298

1.1. Diphenyl Ethers . . . . . . . . . . . . . . . . . . . . . 209 2.3. Chloroacetanilides . . . . . . . . . . . . . . . . . . . 308
1.2. Sulfonylureas . . . . . . . . . . . . . . . . . . . . . . . 212 2.4. 1,3,5-Triazines . . . . . . . . . . . . . . . . . . . . . . 311
1.3. Chloroacetanilides . . . . . . . . . . . . . . . . . . . 223 2.5. Ureas . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 315
1.4. 1,3,5-Triazines . . . . . . . . . . . . . . . . . . . . . . 226 2.6. 2,6-Dinitroanilines . . . . . . . . . . . . . . . . . . . 320
1.5. Ureas . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 231 2.7. Imidazolinones . . . . . . . . . . . . . . . . . . . . . . 324
1.6. 2,6-Dinitroanilines . . . . . . . . . . . . . . . . . . . 237 2.8. Phenoxy Compounds . . . . . . . . . . . . . . . . . 325
1.7. Imidazolinones . . . . . . . . . . . . . . . . . . . . . . 240 2.9. Triazoles . . . . . . . . . . . . . . . . . . . . . . . . . . 332
1.8. Phenoxy Compounds . . . . . . . . . . . . . . . . . 242 2.10. Uracils . . . . . . . . . . . . . . . . . . . . . . . . . . . . 337
1.9. Triazoles . . . . . . . . . . . . . . . . . . . . . . . . . . 250 2.11. Pyridines . . . . . . . . . . . . . . . . . . . . . . . . . . 338
1.10. Uracils . . . . . . . . . . . . . . . . . . . . . . . . . . . . 255 2.12. (Thio)carbamates. . . . . . . . . . . . . . . . . . . . 341
1.11. Pyridines . . . . . . . . . . . . . . . . . . . . . . . . . . 257 2.13. Organophosphorus Compounds. . . . . . . . . 347
1.12. (Thio)Carbamates . . . . . . . . . . . . . . . . . . . 260 2.14. Cyclohexene Oximes . . . . . . . . . . . . . . . . . 349
1.13. Organophosphates . . . . . . . . . . . . . . . . . . . 266 2.15. (Benzo)nitriles . . . . . . . . . . . . . . . . . . . . . . 351
1.14. Cyclohexene Oximes . . . . . . . . . . . . . . . . . 268 2.16. Triazinones . . . . . . . . . . . . . . . . . . . . . . . . 352
1.15. (Benzo)nitriles . . . . . . . . . . . . . . . . . . . . . . 270 2.17. Amides. . . . . . . . . . . . . . . . . . . . . . . . . . . . 353
1.16. Triazinones . . . . . . . . . . . . . . . . . . . . . . . . 271 2.18. Anilides . . . . . . . . . . . . . . . . . . . . . . . . . . . 357
1.17. Amides. . . . . . . . . . . . . . . . . . . . . . . . . . . . 272 2.19. Benzoic Acids. . . . . . . . . . . . . . . . . . . . . . . 358
1.18. Anilides . . . . . . . . . . . . . . . . . . . . . . . . . . . 275 2.20. Quinolinecarboxylic Acids . . . . . . . . . . . . . 360
1.19. Benzoic Acids. . . . . . . . . . . . . . . . . . . . . . . 278 2.21. Benzoylcyclohexanediones . . . . . . . . . . . . . 361
1.20. Quinolinecarboxylic Acids . . . . . . . . . . . . . 279 2.22. Benzofurans . . . . . . . . . . . . . . . . . . . . . . . . 362
1.21. Benzoylcyclohexanediones . . . . . . . . . . . . . 280 2.23. Dicarboximides . . . . . . . . . . . . . . . . . . . . . 362
1.22. Benzofurans . . . . . . . . . . . . . . . . . . . . . . . . 281 2.24. Dinitrophenol Herbicides. . . . . . . . . . . . . . 363
1.23. Dicarboximides . . . . . . . . . . . . . . . . . . . . . 281 2.25. Aliphatic Compounds . . . . . . . . . . . . . . . . 364
1.24. Dinitrophenols . . . . . . . . . . . . . . . . . . . . . . 282 2.26. Inorganic Compounds . . . . . . . . . . . . . . . . 365
1.25. Aliphatic Compounds . . . . . . . . . . . . . . . . 283 2.27. Oxadiazolones . . . . . . . . . . . . . . . . . . . . . . 365
1.26. Inorganic Compounds . . . . . . . . . . . . . . . . 284 2.28. Oxazoles. . . . . . . . . . . . . . . . . . . . . . . . . . . 366
1.27. Oxadiazolones . . . . . . . . . . . . . . . . . . . . . . 284 2.29. Pyrazoles . . . . . . . . . . . . . . . . . . . . . . . . . . 367
1.28. Oxazoles. . . . . . . . . . . . . . . . . . . . . . . . . . . 285 2.30. Pyridazines . . . . . . . . . . . . . . . . . . . . . . . . 369
1.29. Pyrazoles . . . . . . . . . . . . . . . . . . . . . . . . . . 286 2.31. Pyridazinones . . . . . . . . . . . . . . . . . . . . . . 369
1.30. Pyridazines . . . . . . . . . . . . . . . . . . . . . . . . 289 2.32. Quaternary Ammonium Compounds. . . . . 370
1.31. Pyridazinones . . . . . . . . . . . . . . . . . . . . . . 289 2.33. Miscellaneous Compounds . . . . . . . . . . . . . 371
1.32. Quaternary Ammonium Compounds. . . . . 290 References . . . . . . . . . . . . . . . . . . . . . . . . . 375
1.33. Miscellaneous Compounds . . . . . . . . . . . . . 290
2. Toxicology . . . . . . . . . . . . . . . . . . . . . . . . . 296
2.1. Diphenyl Ethers . . . . . . . . . . . . . . . . . . . . . 296

1. Properties of Herbicides C14H7ClF3NO5, Mr 361.66, mp 155160
C, log

Kow 1.18, vapor pressure 0.133 mPa, pKa 3.86, is
1.1. Diphenyl Ethers an off-white to colorless solid which is sparingly
soluble in water, n-hexane, moderately soluble in
Acifluorfen [50594-66-6], 5-(2-chloro-4- acetone, ethanol, dichloromethane, xylene, and
trifluoromethylphenoxy)-2-nitrobenzoic acid, kerosene [1, 2]. The corresponding sodium salt

2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

DOI: 10.1002/14356007.o28_o01
210 Weed Control, 2. Individual Herbicides
[62476-59-9] has the following properties:
C14H6ClF3NO5, Mr 383.64, mp 274278
C, r
1.26, log Kow 3.70, vapor pressure <1.3 mPa, is
light yellow solid, soluble in water and methanol,
moderately soluble in octanol, and sparingly
soluble in hexane [35].
Acifluorfen is produced by reaction of 2-
chloro-4-trifluoromethylphenol with 2-nitro-5-
chlorobenzoic acid [6].
Acifluorfen is a selective contact herbicide
which is absorbed by foliage and roots, with
negligible translocation. It is used pre- and
post-emergence for the control of many annual
broad-leaved weeds, with some effects on
grasses.
Formulation. Liquid concentrate.
Trade Names. Blazer, Doble, Galaxy, Storm,
Ultrablazer, Tackle.
Acifluorfen has a half-life of 54 d in soil and
decomposes under aqueous photolytic conditions
with a half-life of 4 d. It is stable towards aqueous
hydrolysis.
Aclonifen [74070-46-5], 2-chloro-6-nitro-
3-phenoxyaniline, C12H9ClN2O3, Mr 264.66, mp
8182
C, log Kow 4.36, r 1.46 g/mL, vapor
pressure 0.016 mPa, pKa 3.15, consists of yellow
colored crystals which are practically insoluble
in water, moderately soluble in n-hexane, fairly
soluble in methanol, and freely soluble in acetone
and toluene [1, 2, 7, 8].
Aclonifen is manufactured by reaction of 1,2-
dichloro-3-amino-4-nitrobenzene with pheno-
late [9].
Aclonifen is a selective, systemic herbicide
used pre-emergence to control grass and broad-
leaved weeds in winter wheat, potatoes, sun-
flowers, and other crops. It is an inhibitor of the
carotenoid biosynthesis.
Formulation. Soluble concentrate.
Trade Names. Challenge, Bandur, Mikado.
Vol. 39
Half-lives of Aclonifen: in soil 117 d, aque-
ous photolysis 197 d, stable towards aqueous
hydrolysis.
AKH-7088 [104459-82-7], methyl {(E,Z)-
1-[5-(2-chloro-4-trifluoromethylphenoxy)-2-ni-
trophenyl]-2-methoxyethylideneaminooxy}ace-
tate, C19H16ClF3N2O7, Mr 476.79, mp 57.758.1,
bp 490.7
C at 101.1 kPa, log Kow 5.2, r 1.41 g/
mL, vapor pressure 0.3 mPa, forms colorless
crystals which are sparingly soluble in water, and
soluble in dichloromethane and toluene [1, 10].
AKH-7088 is produced by reaction of 2-
chloro-p-trifluoromethylphenolate with 3-meth-
oxyethylidineamino-oxyacatate 4-nitrochloro-
benzene [11].
AKH-7088 is used post-emergence to control
broad-leaved weeds, and velvet leaf in soya
beans. It is activated by light, and acts by inhibi-
tion of protoporphyrinogen oxidase.
Formulation. Emulsifiable concentrate, wet-
table powder.
Trade Name. Challenge.
Bifenox [42576-02-3], methyl 5-(2,4-di-
chlorophenoxy)-2-nitrobenzoate, C14H9Cl2NO5,
Mr 342.13, mp 8486
C, log Kow 4.48, r
1.155 g/mL, vapor pressure 0.162 mPa, consists
of yellow crystals which are practically insoluble
in water, moderately soluble in methanol, readily
soluble in dichloromethane, acetone, chloroben-
zene, xylene, and ethanol, and slightly soluble in
aliphatic hydrocarbons [13, 12, 13].
Bifenox is produced by reaction of potassium
2,4-dichlorophenolate with methyl 5-chloro-2-
nitrobenzoate [14].
Bifenox acts by cellular membrane disruption
and by inhibition of photosynthesis. It is a selec-
tive herbicide absorbed through foliage and new
shoots, used to control broad-leaved weeds and
some grasses in cereals, maize, and soya beans.
Vol. 39
Formulation. Soluble concentrate
Trade Names. Modown, Tolkan., Fox,
Sabine.
Bifenox has half-lives of 6 d in soil, 0.11 d in
water-sediment, and is photolyzed and hydro-
lyzed in aqueous medium with half-lives of 2.2
and 265 d, respectively.
Chlomethoxyfen [32861-85-1], 5-(2,4-di-
chlorophenoxy)-2-nitroanisole, C13H9Cl2NO4,
Mr 314.12, mp 113114
C, log Kow 3.34, r
1.37 g/mL, vapor pressure 1.87 mPa, consists of
yellow crystals which are practically insoluble in
water, readily soluble in acetone, dimethyl sulf-
oxide, and benzene [1, 2].
Chlomethoxyfen is obtained by reaction of
2,4-dichlorophenolate with 1-chloro-3-meth-
oxy-4-nitrobenzene [15].
Chlomethoxyfen is a selective, systemic con-
tact herbicide, rapidly absorbed by roots but with
limited translocation, used pre-emergence for the
control of annual weeds in transplanted rice. It
acts by inhibition of protoporphyrinogen
oxidase.
Formulation. Granules.
Trade Names. Diphenex; Ekkusugoni, Dife-
nex, Condore.
Ethoxyfen-ethyl [131086-42-5], ethyl O-
[2-chloro-5-(2-chloro-a,a,a-trifluoro-p-toly-
loxy)benzoyl]- L -lactate, C 19 H 15Cl 2F 3O 5, M r
450.37, is a brown oily viscous liquid which is
sparingly soluble in water, readily soluble in
acetone, methanol, toluene and xylene [1, 2, 16].
Ethoxyfen-ethyl is produced by reaction of 2-
chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]
benzoyl chloride with ethyl lactate [17].
Ethoxyfen-ethyl acts by accumulation of tet-
rapyrrole and protoporphyrin. It is a contact,
post-emergence herbicide for the control of
broad-leaved weeds in winter wheat, barley,
peas, soya beans, and peanuts.
Weed Control, 2. Individual Herbicides 211
Formulation. Emulsifiable concentrate,
emulsifiable granules.
Trade Names. Buvirex, HC-252.
Fluoroglycofen-ethyl [77501-90-7], ethyl
O-[5-(2-chloro-a,a,a-trifluoro-p-tolyloxy)-2-ni-
trobenzoyl]glycolate, C18H13ClF3NO7, Mr 447.75,
mp 5054
C, log Kow 3.65, r 1.28 g/mL, vapor
pressure 53 nPa, is a dark brown to tan solid with a
musky odor, which is practically insoluble in
water, slightly soluble in methanol, moderately
soluble in hexane, and soluble in acetonitrile and
many other organic solvents [1, 2, 18].
Fluoroglycofen-ethyl is produced by reaction
of 5-[2-chloro-4-(trifluoromethyl)phenyl]-2-ni-
trobenzoyl chloride with ethyl hydroxyacetate
in the presence of trimethylamine [19].
Fluoroglycofen-ethyl is a selective, foliar-ap-
plied, leaf and root herbicide used to control
broad-leaved weeds and grasses in wheat, barley,
oats, peanuts, rice, and soya beans. It inhibits
protoporphyrinogen oxidase.
Formulation. Wettable powder, emulsifiable
concentrate.
Trade Names. Compete, Satis, Simtar, Super
Blazer, Competitor.
Fluoroglycofen-ethyl has half-lives of 2 d in
soil, 0.25 and 14 d under aqueous photolysis and
hydrolysis conditions, respectively, and 50 d in
water-sediment.
Fomesafen [72178-02-0], N-[5-(2-chloro-
4-trifluoromethylphenoxy)2-nitrophenyl]metha-
nesulfonamide, C15H10ClF3N2O6S, Mr 438.76,
mp 220221
C, log Kow 2.9, r 1.61 g/mL, pKa
2.83, vapor pressure 4.0 mPa, forms colorless
crystals which are sparingly soluble in water and
xylene, moderately soluble in methanol and di-
chloromethane, and readily soluble in acetone
[13, 2022].
Fomesafen is manufactured by reaction of
2-chloro-4-trifluoromethylphenolate with 4-
212 Weed Control, 2. Individual Herbicides
chloro-N-methylsulfonyl-2-nitrobenzamide
[23].
Fomesafen is a selective, contact herbicide
which is absorbed by both leaves and roots. It is
used in early post-emergence for the control of
broad-leaved weeds in soya beans. It is an inhib-
itor of protoporphyrinogen oxidase.
Formulation. Liquid concentrate, soluble
concentrate.
Trade Names. Flex, Reflex.
Fomesafen is stable towards aqueous photol-
ysis, and decays with half-lives of 89 d in soil and
7 d in water-sediment.
Lactofen [77501-63-4], ethyl O-[5-(2-
chloro-a,a,a-trifluoro-p-tolyloxy)-2-nitroben-
zoyl]-DL-lactate, C19H15ClF3NO7, Mr 461.77, mp
4446
C, bp 494
C at 101 kPa, log Kow 4.81, r
1.39 g/mL, vapor pressure 0.0093 mPa, is a dark
brown to colorless solid which is sparingly solu-
ble in water, and soluble in many organic sol-
vents [13, 5, 24].
Lactofen is produced by reaction of 2-chloro-
4-trifluoromethylphenolate with ethyl 2-nitro-5-
chlorobenzoyllactate [25].
Lactofen is a selective broad-spectrum herbi-
cide applied pre- and post-emergence to control
broad-leaved weeds in cereals, potatoes, soya
beans, rice, and peanuts. It is absorbed by foliage
with limited translocation and inhibits protopor-
phyrinogen oxidase.
Formulation. Emulsifiable concentrate.
Trade Names. Cobra, Stellar, PPG-844.
Lactofen has a half-life of 4 d in soil.
Nitrofen [1836-75-5], 2,4-dichlorophenyl
4-nitrophenyl ether, C12H7Cl2NO3, Mr 284.10,
mp 7071
C, bp 180190
C at 33 Pa, log Kow
5.54, r 1.33, vapor pressure 1.06 mPa, is a
colorless crystalline solid which is sparingly
soluble in water, moderately soluble in ethanol,
freely soluble in n-hexane, benzene, acetone,
methanol, and xylene [2, 3, 26, 27].
Vol. 39
Nitrofen can be made by reaction of 2,4-
dichlorophenol with p-chloronitrophenol in the
presence of a base [3].
Nitrofen is a contact herbicide applied pre-
and post-emergence to control annual grasses
and broadleaved weeds on a variety of crops,
e.g., cereals, rice, sugar beets, vegetables, and
ornamentals. It acts by inhibition of cyclic elec-
tron transport, disrupting photosynthesis.
Formulation. Granules, emulsifiable concen-
trate, wettable powder.
Trade Names. Mezotox, Niclofen, NIPR,
Tokkorn.
Nitrofen is stable towards aqueous hydrolysis
and photolysis, and decomposes in soil with a
half-live of 10 d.
Oxyfluorfen [42874-03-3], 2-chloro-4-tri-
fluoromethylphenyl- 3-ethoxy-4-nitrophenyl
ether, C15H11ClF3NO4, Mr 361.72, mp 8590
C,
bp 358
C, log Kow 4.86, r 1.53 g/mL, vapor
pressure 0.026 mPa, is an orange crystalline
solid which is practically insoluble in water,
moderately soluble in heptane, fairly soluble in
methanol, and readily soluble in acetone and
ethyl acetate [13, 2830].
Oxyfluorfen is manufactured by reaction of
3,4-dichlorobenzotrifluoride with resorcinol; the
resulting product is then treated with ethanol in
the presence of potassium hydroxide [31].
Oxyfluorfen is a selective contact herbicide
used pre- and post-emergence for the control of
annual broad-leaved weeds in a variety of tropi-
cal and subtropical crops. It inhibits protopor-
phyrinogen oxidase.
Formulation. Granules, suspension concen-
trate, emulsifiable concentrate.
Trade Names. Goal, Galigan, Double, Scuola.
Oxyfluorfen shows the following half-lives: in
soil 35 d, aqueous photolysis 5.6 d, is stable
towards aqueous hydrolysis.
1.2. Sulfonylureas
Amidosulfuron [120923-37-7], 1-(4,6-di-
methoxypyrimidin-2-yl)-3-mesyl(methyl)sulfa-
moylurea, C9H15N5O7S2, Mr 369.4, mp 179
C,
Vol. 39
log Kow 1.56, r 1.51 g/mL, pKa 3.58, vapor
pressure 0.013 mPa, is a colorless crystalline
powder which is insoluble in hexane, slightly
soluble in acetone and toluene, and moderately
soluble in water, ethyl acetate, and isopropyl
alcohol [1, 2, 32, 33].
Amidosulfuron is produced by reaction of N-
methylmesylsulfonamide with chlorosulfonyl
isocyanate, followed by treatment with 2-ami-
no-4,6-dimethoxypyrimidine [34].
Amidosulfuron is a selective, systemic herbi-
cide, absorbed by leaves and roots, used post-
emergence for the control of a wide range of
broad-leaved weeds, especially cleavers, in win-
ter wheat, durum wheat, barley, rye, and oats. It
inhibits amino acid biosynthesis.
Formulation. Spray application.
Trade Names. Artemis, Druid, Sekator,
Squire, Eagle.
Amidosulfuron is stable towards aqueous
photolysis and hydrolysis; in soil its half-life is
21 d.
Azimsulfuron [120162-55-2], 1-(4,6-di-
methoxypyrimidin-2-yl)-3-[1-methyl-4-(2-
methyl-2H-tetrazol-5-yl)pyrazol-5-ylsulfonyl]
urea, C13H16N10O5S, Mr 424.40, mp 170
C, log
Kow 0.043, r 1.12 g/mL, pKa 3.6, vapor pressure
4.0 mPa, is a colorless powder which is moder-
ately soluble in water, methanol, and toluene, and
soluble in acetone, acetonitrile, and ethyl acetate
[1, 2, 35, 36].
Azimsulfuron is produced by reaction of 2-(1-
methyl-1H-diazol)-4-(1-methyl-1H-tetrazol)-
sulfonamide with 2-(4,6-dimethoxypyrimidine)
isocyanate [37].
Azimsulfuron is a post-emergence herbicide
with mainly foliar uptake. It is used to control
annual and perennial broad-leaved and sedge
Weed Control, 2. Individual Herbicides 213
weeds in southern European rice. It acts by
inhibition of acetolactate synthase.
Formulation. Water-dispersible granules.
Trade Name. Gulliver.
Azimsulfuron has half-lives of 24 d in soil,
164 d by aqueous photolysis, 124 d by aqueous
hydrolysis, and 112 d in water-sediment.
Bensulfuron-methyl [83055-99-6], methyl
a-[(4,6-dimethoxypyrimidin-2-ylcarbamoy)lsul-
famyl]-o-toluate, C16H18N4O7S, Mr 410.40, mp
179.4
C, log Kow 0.79, r 1.41, pKa 5.2, vapor
pressure 2.8 fPa, is a colorless to pale yellow solid
which is sparingly soluble in water, xylene, fairly
soluble in acetone, acetonitrile, and ethyl acetate,
and soluble in dichloromethane [1, 2, 38].
Bensulfuron-methyl is produced by the reac-
tion between 2-carboxymethyl benzylsulfamoyl
chloride and 2-amino-4,6-dimethoxypyrimidine
[39].
Bensulfuron-methyl is a selective, systemic
herbicide, absorbed by foliage and roots, used
pre- and post-emergence for the control of annual
and perennial weeds and sedges in continuously
flooded rice. It inhibits amino acid biosynthesis.
Formulation. Water-dispersible granules.
Trade Names. Fujigrass, Londax, Zark,
Wolf-Ace
Bensulfuron-methyl decays in soil with a half-
life of 24 d, the photolytic half-life is 43 d, and in
water-sediment it amounts to 48 d. It is stable
towards aqueous hydrolysis.
Chlorimuron-ethyl [90982-32-4], ethyl 2-
(4-chloro-6-methoxypyrimidin-2-ylcarbamoyl-
sulfamoyl)benzoate, C15H15ClN4O6S, Mr 414.82,
mp 181
C, log Kow 2.50, r 1.51 g/mL, pKa 4.2,
vapor pressure 0.49 nPa, consists of colorless
crystals which are sparingly soluble in water and
n-hexane, moderately soluble in xylene and ben-
zene, and soluble in acetone [13, 40].
214 Weed Control, 2. Individual Herbicides
Chlorimuron-ethyl is produced by reaction of
ethyl 2-sulfamoylchloride benzoic acid with 2-
amino-4-chloro-6-methoxypyrimidin [41].
Chlorimuron-ethyl is used post-emergence
for the control of broad-leaved weeds in soya
beans, peanuts, and a range of other crops. It acts
by inhibition of acetolactate synthase.
Formulation. Dry, water-dispersible gran-
ules, granules.
Trade Names. Classic, Darban, Concert,
Mulexyl.
Chlorimuron-ethyl shows half-lives of 40 and
21 d in soil and aqueous hydrolysis, respectively.
Chlorsulfuron [64902-72-3], 1-(2-chloro-
phenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-
triazin-2-yl)urea, C12H12ClN5O4S, Mr 357.77,
mp 174178
C, log Kow 0.99, r 1.48 g/mL,
pKa 3.4, vapor pressure 3.07 nPa, is a colorless
crystalline solid which is moderately soluble in
toluene, fairly soluble in water, acetone, and
methanol, readily soluble in dichloromethane
[13, 4244].
Chlorsulfuron is produced by reaction of 2-
sulfonylisocyanate chlorobenzene with 2-amino-
4,6-dimethoxy-1,3,5-triazine [45].
Chlorsulfuron is a selective, systemic herbi-
cide, absorbed by roots and foliage, used pre- and
early post-emergence for the control of most
broad-leaved weeds and some grasses in wheat,
barley, oats, rye, and noncropland.
Formulation. Water-dispersible granules,
dry formulation.
Trade Names. Glean, Telar, Lasher.,
Hammer.
Chlorsulfuron decays with half-lives of 160,
18.8, and 26 d in soil, by aqueous photolysis, and
in water-sediment, respectively. It is stable to-
wards aqueous hydrolysis.
Cinosulfuron [94593-91-6], 1-(4,6-di-
methoxy-1,3,5-triazin-2-yl)-3-[2-(2-methox-
yethoxy)phenylsulfonyl]urea, C15H19N5O7S, Mr
413.45, mp 140145
C, log Kow 0.2, r 1.47 g/
mL, pKa 4.72, vapor pressure 0.01 mPa, is a
colorless crystalline powder which is slightly
soluble in toluene and n-octanol, moderately
Vol. 39
soluble in water and ethanol, and readily soluble
in acetonen-octanol [1, 2].
Cinosulfuron is produced by reaction of 2-
methoxyethoxy sulfamoyl chlorobenzene with
2-amino-4,6-dimethoxy-1,3,5-triazine [46].
Cinosulfuron is used post-emergence to con-
trol many weeds in transplanted, directly seeded,
wet-sown, water-sown, and dry-sown flooded
rice crops. It is also used in tropical plantation
crops. It is absorbed by roots and shoots and is an
acetolactate synthase inhibitor.
Formulation. Water-dispersible granules.
Trade Name. Setoff.
Cinosulfuron has a half-life of 20 d in soil, and
is stable towards aqueous hydrolysis.
Cyclosulfamuron [136849-15-5], 1-[2-(cy-
clopropylcarbonyl)phenylsulfamoyl]-3-(4,6-di-
methoxypyrimidin-2-yl)urea, C17H19N5O6S, Mr
421.43, mp 160.9162.9
C, log Kow 1.41, r
1.532 g/mL, pKa 5.04, vapor pressure
0.022 mPa, is an almost colorless solid which
is practically insoluble in water [1, 2].
Cyclosulfamuron is produced by reaction of
2-amino-4,6-dimethoxypyrimidine with isocya-
nate sulfamoyl chloride, followed by treatment
with o-aminophenyl cyclopropyl ketone [47].
Cyclosulfamuron, which inhibits acetolactate
synthase, is used to control a variety of dicotyle-
donous and sedge weeds in rice, wheat, and
barley.
Formulation. Wettable powder.
Trade Names. Jin-Qui, Savior.
Ethametsulfuron-methyl [97780-06-8],
methyl 2-[(4-ethoxy-6-methylamino-1,3,5-tria-
zin-2-yl)carbamoylsulfamoyl]benzoate,
C15H18N6O6S, Mr 410.41, mp 194
C, log Kow
0.89, pKa 4.6, consists of colorless to light tan
colored crystals which are sparingly soluble in
Vol. 39
water and hexane, moderately soluble in aceto-
nitrile, ethanol, methanol, and dichloromethane,
and soluble in acetone [1, 2].
Ethametsulfuron-methyl is produced by reac-
tion of methyl 2-sulfamoylbenzoate with 4-eth-
oxy-6-methylamino-1,3,5-triazin-2-yl isocya-
nate [48].
Ethametsulfuron-methyl is an effective her-
bicide used post-emergence to control wild mus-
tard, stinkweed, and other broad-leaved weeds in
oilseed rape.
Formulation. Wettable powder, dry
flowable.
Trade Name. Muster.
Ethametsulfuron-methyl decays in soil with a
half-life of 70 d. It is stable towards aqueous
hydrolysis.
Ethoxysulfuron [126801-58-9], 1-(4,6-di-
methoxypyrimidin-2-yl)-3-(2-ethoxyphenoxy-
sulfonyl)urea, C15H18N4O7S, Mr 398.39, mp
150
C, log Kow 1.01, r 1.44 g/mL, pKa 5.28,
vapor pressure 0.066 mPa, is a colorless to beige
powder which is insoluble in hexane, moderately
soluble in water, toluene, and methanol, and
soluble in acetone [1, 2, 49].
Ethoxysulfuron is produced by reaction of 2-
ethoxyphenoxysulfonyl isocyanate with 2-ami-
no-4,6-dimethoxypyrimidine [50].
Ethoxysulfuron is a plant growth regulator
(inhibition of acetolactate synthase) used for the
control of broad-leaved and sedge weeds in
cereals, rice, and sugar cane, tea, and hops.
Formulation. Water-dispersible powder.
Trade Name. Sunrice.
Ethoxysulfuron decays in soil with a half-life
18 d, and in water-sediment with a half-life of
30 d. The half-lives for aqueous photolytic and
hydrolytic degradation are 30 and 259 d,
respectively.
Weed Control, 2. Individual Herbicides 215
Flazasulfuron [104040-78-0], 1-(4,6-di-
methoxypyrimidin-2-yl)-3-(3-trifluoromethyl-
2-pyridylsulfonyl)urea, C13H12F3N5O5S, Mr
407.37, mp 180
C, log Kow 0.06, r 1.62 g/
mL, pKa 4.37, vapor pressure 0.0133 mPa, is a
colorless crystalline solid which is practically
insoluble in n-hexane, moderately soluble in
water and ethyl acetate, and soluble in dichlor-
omethane [1, 2, 51, 52].
Flazasulfuron is produced by reaction of 2-
sulfamoylchloride-3-trifluoromethylpyridine
with 2-amino-4,6-dimethoxypyrimidine [53].
Flazasulfuron is a systemic herbicide, ab-
sorbed through leaves, used post-emergence for
the control of grass and broad-leaved weeds and
sedges in warm-season turf.
Formulation. Wettable granules.
Trade Names. Katana, Shibagen.
Flazasulfuron decays in soil with a half-life of
10 d and in water-sediment with a half-life of
23 d. It is stable towards aqueous photolysis; its
hydrolytic half-life is 11 d.
Flucetosulfuron [412928-75-7],
(1RS,2RS;1RS,2SR)-1-{3-[(4,6-dimethocypyri-
midin-2-ylcarbamoyl)sulfamoyl]-2-pyridyl}-2-
fluoropropyl methoxyacetate, C18H22FN5O8S,
Mr 487.5, mp 180
C, log Kow 1.05, pKa 3.5,
vapor pressure 0.086 mPa, is a colorless solid
which is sparingly soluble in water and n-hexane,
moderately soluble in methanol, and soluble in
acetone and ethyl acetate [1].
Flucetosulfuron can be prepared by reaction of
3-sulfamoylchloride-2-(20 -methoxyacetyl)fluor-
opropylpyridine with 2-amino-4,6-dimethoxy-
pyrimidine in the presence of a base [54].
Flucetosulfuron, a new herbicide with a broad
spectrum of activities, is absorbed by roots and
leaves, and is used post-emergence to control
216 Weed Control, 2. Individual Herbicides
broad-leaved weeds, some grass weeds, and
sedges in rice and in some cereal crops. It inhibits
acetolactate synthase.
Formulation. Granules, wettable powder.
Trade Name. Fluxo.
Flupyrsulfuron-methyl-sodium [144740-
54-5], sodium (4,6-dimethoxypyrimidin-2-yl)
[({[3-(methoxycarbonyl)-6-(trifluoromethyl)
pyridine-2-yl]sulfonyl}amino)carbonyl]aza-
nide, C15H13F3N5NaO7S, Mr 487.3, mp 165
170
C, log Kow 1.16, r 1.55 g/mL, pKa 4.94,
vapor pressure 1.0 nPa, is a colorless powder
which is sparingly soluble in benzene, moderate-
ly soluble in water and ethyl acetate, and soluble
in dichloromethane and acetone [1, 2, 55].
Flupyrsulfuron-methyl-sodium is produced
by reaction of methyl 2-aminosulfonyl-6-tri-
fluoromethyl-3-pyridine carboxylate with 4,6-
dimethoxypyrimidin-2-yl isocyanate [56].
Flupyrsulfuron-methyl-sodium is a selective
post-emergence herbicide used for the control of
black grass and broad-leaved weeds in cereals. It
is an acetolactate synthase inhibitor.
Formulation. Wettable granules.
Trade Names. Bullian, Excalibur, Lancer.
Flupyrsulfuron-methyl sodium has half-lives
of 13 d in soil and 5 d in water-sediment, and the
half-lives for aqueous photolytic and hydrolytic
degradation are 8.7 and 12 d, respectively.
Foramsulfuron [173159-57-4], 1-(4,6-di-
methoxypyrimidin-2-yl)-3-[2-(dimethylcarba-
moyl)-5-formamidophenylsulfonyl]urea,
C17H20N6O7S, Mr 452.5, mp 199.5
C, log Kow
0.166, r 1.44 g/mL, pKa 4.6, vapor pressure 42 fPa,
is a light beige powder which is sparingly soluble in
heptane, ethyl acetate, moderately soluble in water,
acetone, and methanol [2, 57, 58].
Vol. 39
Foramsulfuron can be synthesized by reac-
tion of N,N-dimethyl 2-sulfamoylchloride-4-
formylamino benzamide with 2-amino-4,6-di-
methoxypyrimidine in the presence of a base
[54]
Foramsulfuron is a post-emergence herbicide
used against annual and perennial grasses and
broad-leaved weeds in corn grain, corn forage,
and corn stover.
Formulation. Foliar spray.
Trade Name. Option.
Foramsulfuron decays with half-lives of 5.5
and 128 d in soil and by aqueous hydrolysis,
respectively. It is stable towards photolysis.
Halosulfuron-methyl [100784-20-1],
methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-
ylcarbamoylsulfamoyl)-1-methylpyrazole-4-car-
boxylate, C13H15ClN6O7S, Mr 434.81, mp 175.5
177.2
C, log Kow 0.02, r 1.62 g/mL, pKa 3.44,
vapor pressure 0.01 mPa, is a colorless powder
which is moderately soluble in water and metha-
nol [1, 2].
Halosulfuron-methyl is produced by reaction
of N-1-methyl-3-chloro-4-carboxymethyl-5-sul-
fonylisocyanate pyrazole with 2-amino-4,6-di-
methoxypyrimidine [59].
Halosulfuron-methyl is a systemic, selective
herbicide used to control annual broad-leaved
weeds and nutsedge sp. in maize, sugar cane,
and turf. It acts by inhibition of the biosynthesis
of the essential amino acids valine and
isoleucine.
Formulation. Water-dispersible granules.
Trade Name. Manage, Permit.
Halosulfuron-methyl decays in soil with a
half-life of 55 d.
Imazosulfuron [122548-33-8], 1-(2-chlor-
oimidazo[1,2-a]pyridin-3-ylsulfonyl)-3-(4,6-di-
methoxypyrimidin-2-yl)urea, C14H13ClN6O5S,
Mr 412.81, mp 183184
C, log Kow 1.72, r
1.52 g/mL, pKa 2.2, vapor pressure 45 nPa, is
a colorless crystalline powder which is sparingly
soluble in water and xylene, moderately soluble
in ethyl acetate and acetone, and soluble in
dichloromethane [1, 2].
Vol. 39
Imazosulfuron is produced by reaction of 2-
chloroimidazo[1,2-a]pyridine sulfonylisocya-
nate with 2-amino-4,6-dimethoxypyrimidine
[60].
Imazosulfuron is used to control most annual
and perennial broad-leaved weeds and sedges in
paddy rice and turf. It is absorbed by roots and
translocated, and inhibits acetolactate synthase.
Formulation. Granules.
Trade Name. Sibatito.
Imazosulfuron decays in soil with a half-life
of 50 d.
Iodosulfuron-methyl sodium [144550-36-
7], sodium ({[5-iodo-2-(methoxycarbonyl)phe-
nyl]sulfonyl}carbamoyl)(4-methoxy-6-methyl-
1,3,5-triazin-2-yl) azanide, C14H13IN5NaO6S,
Mr 529.24, mp 150
C, log Kow 1.59, r 1.76 g/
mL, pKa 3.22, vapor pressure 6.7 nPa, is a
colorless crystalline solid which is sparingly
soluble in n-heptane and n-hexane, moderately
soluble in toluene, and soluble in water and
methanol [2, 61, 62].
Iodosulfuron-methyl sodium can be prepared
by reaction of methyl 2-sulfamoylchloride-4-io-
dobenzoate with 2-amino-4,6-dimethoxypyrimi-
dine in the presence of a base, followed by the
transformation into the sodium salt [54].
Iodosulfuron-methyl sodium is a selective,
post-emergence herbicide used to control grasses
and broad-leaved weeds in cereals. It inhibits
acetolactate synthase.
Formulation. Wettable granules.
Trade Names. Atlantis, Chekkar, Hussar,
Othello.
Iodosulfuron-methyl sodium decays in soil
with a half-life of 8 d, and in water-sediment
with one of 19 d. It is stable towards aqueous
hydrolysis but decomposes photolytically with a
half-life of 50 d.
Weed Control, 2. Individual Herbicides 217
Mesosulfuron-methyl [208465-21-8],
methyl 2-[(4,6-dimethoxypyrimidin-2-yl)sul-
famoyl]-a-(methanesulfonamido)-p-toluate,
C17H21N5O9S2, Mr 503.51, mp 195.4
C, log
Kow 0.48, r 1.48 g/mL, pKa 4.35, vapor pres-
sure 11 fPa, is a cream-colored granular solid
which is slightly soluble in water, hexane, and
toluene, moderately soluble in ethyl acetate,
and soluble in acetone [2, 63, 64].
Mesosulfuron-methyl can be made by reac-
tion of methyl 2-sulfamoylchloride benzoate
with 2-amino-4,6-dimethoxypyrimidine in the
presence of a base [54, 65].
Mesosulfuron is used post-emergence to con-
trol grasses and some broad-leaved weeds in
cereals. It inhibits amino acid biosynthesis.
Formulation. Wettable granules.
Trade Names. Atlantis, Othello, Pacifica,
Osprey, Silverado.
Mesosulfuron decomposes in soil with a half-
life of 5366 d, and in water-sediment with a half-
life of 49 d. The half-lives of its aqueous photolysis
and hydrolysis are 46 and 253 d, respectively.
Metazosulfuron [868680-84-6], 1-{3-
chloro-1-methyl-4-[(5RS)-5,6-dihydro-5-methyl-
1,4,2-dioxazin-3-yl]pyrazol-5-ylsulfonyl}-3-(4,6-
dimethoxypyrimidin-2-yl)urea, C15H18ClN7O7S,
Mr 475.86 [66].
Metazosulfuron can be prepared by reaction
of 1-methyl-3-chloro-4-(5,6-dihydro-5-methyl)-
1,4,2-dioxazine-5-sulfamoylchloride pyrazole
with 2-amino-4,6-dimethoxypyrimidine in the
presence of a base [54].
No further data are available yet on this new
herbicide.
218 Weed Control, 2. Individual Herbicides
Metsulfuron-methyl [74223-64-6], meth-
yl 2-(4-methoxy-6-methyl-1,3,5-triazin-2-yl-
carbamoylsulfamoyl)benzoate, C14H15N5O6S,
Mr 381. 36, mp 162163
C, log Kow 1.7, r
1.45 g/mL, pKa 3.75,vapor pressure 0.11 nPa,
consists of colorless crystals which are practi-
cally insoluble in n-hexane, fairly soluble in
water, xylene, ethanol, and methanol, and solu-
ble in dichloromethane, and acetone [13, 5, 67,
68].
Metsulfuron-methyl is produced by reaction
of 2-sulfamoylchloride benzoic acid with 2-ami-
no-4-methoxy-6-methyl-1,3,5-triazine [69].
Metsulfuron-methyl is a selective systemic
herbicide with contact activity used to control
a wide range of annual and perennial broad-
leaved weeds in wheat, barley, rice, and oats,
fallow and noncropland by pre- or post-emer-
gence application. It acts by inhibition of amino
acid biosynthesis.
Formulation. Wettable granules, dry flow-
ables, water-soluble granules.
Trade Names. Ally, Malban, Quit, Express,
Cimarron, Concest, Escort, Pike.
Metsulfuron-methyl decays with a half-life of
10 d in soil, and with a half-life of 140 d in water-
sediment. It is stable towards aqueous photolysis
and hydrolysis.
Nicosulfuron [111991-09-4], 2-[(4,6-di-
methoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-
N,N-dimethylnicotinamide, C15H18N6O6S, Mr
410.41, mp 141144
C, log Kow 0.61, r
0.31 g/mL, pKa 4.78, vapor pressure 0.8 nPa,
consists of colorless crystal which are slightly
soluble in methanol, moderately soluble in water,
and readily soluble in acetone, ethanol, chloro-
form, dimethylformamide, acetonitrile, and di-
chloromethane [1, 2, 5, 7072].
Vol. 39
Nicosulfuron is produced by reaction of 2-
sulfamoylchloride-3-N-dimethylaminocarboxy-
pyridine with 2-amino-4,6-dimethylpyrimidine
[73].
Nicosulfuron is a selective, systemic herbi-
cide, absorbed by roots and leaves and translo-
cated, used post-emergence to control annual
grass weeds in maize. It acts by inhibition of
acetolactate synthase.
Formulation. Suspension concentrate.
Trade Names. Accent, Dasul, Milagro, Buc-
ket, Samson, Beliur.
Nicosulfuron decomposes with half-lives of
26, 202, and 41.5 d in soil, photolytically, and in
water-sediment, respectively. It is stable towards
hydrolytic action.
Orthosulfamuron [213464-77-8], 1-(4,6-
dimethoxypyrimidin-2-yl)-3-[2-(dimethylcarba-
moyl)phenylsulfamoyl]urea, C16H20N6O6S, Mr
424.4, mp 157
C, log Kow 1.31, r 1.48 g/mL,
vapor pressure 0.111 mPa, is a grayish to color-
less solid which is slightly soluble in water,
moderately soluble in ethyl acetate, methanol,
soluble in acetone, xylene, and dichloromethane
[2, 74, 75].
Orthosulfamuron can be synthesized by reac-
tion of N,N-dimethyl 2-sulfamoylchloride benz-
carbamate with 2-amino-4,6-dimethoxypyrimi-
dine in the presence of a base [54].
Orthosulfamuron is a systemic herbicide,
absorbed by foliage and roots and translocated,
used in rice pre- and post-emergence to
control sedges, grasses, and some broad-leaved
weeds. It acts by inhibition of acetolactate
synthase.
Formulation. Wettable granules, water-dis-
persible granules, granules.
Trade Names. Strada, IR5878.
Orthosulfamuron decays with a half-lives of
50 and 180 d in soil and photolytically, respec-
tively. It is stable towards aqueous hydrolysis.
Vol. 39
Oxasulfuron [144651-06-9], oxetan-3-yl 2-
[(4,6-dimethylpyrimidin-2-yl)-carbamoylsulfa-
moyl]benzoate, C17H18N4O6S, Mr 406.41, mp
158
C (decomp.),log Kow 0.81, r 1.41 g/mL,
pKa 5.1, vapor pressure 0.002 mPa, is a colorless
powder which is practically insoluble in n-hex-
ane, sparingly soluble in toluene, and moderately
soluble in water, methanol, and acetone [1, 2].
Oxasulfuron is produced by reaction of 2-
[[(3-oxetanyl)oxy]carbonyl]benzenesulfonamide
with 4,6-dimethylpyrimidine-2-yl carbamate
[76].
Oxasulfuron is used post-emergence for the
control of broad-leaved weeds and grasses in
soya beans. It is absorbed by roots and shoots,
and translocated. It acts by inhibition of aceto-
lactate synthase.
Formulation. Wettable granules
Trade Names. Expert, Dynam.
Oxasulfuron decays with half-lives of 10, 3.5,
8.5 and 22 d in soil, photolytically, hydrolytical-
ly, and in water-sediment, respectively.
Primisulfuron-methyl [86209-51-0], me-
thyl 2-[4,6-bis(difluoromethoxy)pyrimidin-2-yl-
carbamoylsulfamoyl]benzoate, C15H12F4N4O7S,
Mr 468.34, mp 194.8197.4
C, log Kow 0.06, r
1.61 g/mL, pKa 5.1, vapor pressure 5 mPa, is a
fine colorless powder which is sparingly soluble
in water, n-hexane, n-octanol, moderately soluble
in ethanol and toluene, and readily soluble in
acetone [13, 5, 77].
Primisulfuron-methyl is produced by reaction
of 2-sulfamoylchloride benzoic acid with 2-ami-
no-4,6-difluoromethoxypyrimidine [78].
Primisulfuron-methyl is a selective, systemic
herbicide, absorbed through roots and foliage,
used post-emergence for the control of problem
weeds and many broad-leaved weeds in maize,
Weed Control, 2. Individual Herbicides 219
other crops and noncropland. It is an acetolactate
synthase inhibitor.
Formulation. Wettable granules.
Trade Names. Beacon, Tell.
Primisulfuron-methyl decays with half-lives
of 27 and 41 d in soil and hydrolytically,
respectively.
Propyrisulfuron [570415-88-2], 1-(2-
chloro-6-propylimidazo[1,2-b]pyridazin-3-yl-
sulfonyl)-3-(4,6-dimehtoxypyrimidin-2-yl)urea,
C16H18ClN7O5S, Mr 455.88, mp >193.5
C, bp
218.9
C, log Kow 2.9, r 1.775 g/mL, vapor
pressure < 10 mPa, is a colorless crystalline solid
which is practically insoluble in water [79, 80].
Propyrisulfuron can be made by reaction of 2-
chloro-3-sulfamoylchloride-6-propylimidazol
[1,2-b]pyridazine with 2-amino-4,6-dimethoxy-
pyrimidine in the presence of a base [54].
Propyrisulfuron is under registration in Japan.
It will be used in paddy rice to control grasses and
weeds.
Formulation. Granules, wettable powders.
Trade Names. To be announced.
Propyrisulfuron decays photolytically and hy-
drolytically with half-lives of 25 and 77 d,
respectively.
Prosulfuron [94125-34-5], 1-(4-methoxy-
6-methyl-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluor-
opropyl)phenylsulfonyl]urea, C15H16F3N5O4S,
Mr 419.38, mp 155
C (decomp.), log Kow 1.5,
r 1.45 g/mL, pKa 3.76, vapor pressure 3.5 mPa,
consists of colorless crystals which are moder-
ately soluble in water, toluene, ethanol, and
readily soluble in acetone, ethyl acetate, and
dichloromethane [1, 2, 81].
220 Weed Control, 2. Individual Herbicides
Prosulfuron is produced by reaction of 2-
(3,3,3-trifluoropropyl)phenylsulfamoylchloride
with 2-amino-4-methyl-6-methoxypyrimidine
[82].
Prosulfuron is a selective herbicide used post-
emergence on maize, sorghum, cereals (field
corn, white corn, popcorn), pasture, and turf for
broad-spectrum control of annual broad-leaved
weeds. It is absorbed by leaves and roots, and acts
as an inhibitor of acetolactate synthase.
Formulation. Water-dispersible granules.
Trade Names. Exceed, Peak, Jester
Prosulfuron decomposes with half-lives of 16,
242, and 130 d in soil, photolytically, and in
water-sediment, respectively. It is stable towards
hydrolysis.
Pyrazosulfuron-ethyl [93697-74-6], ethyl
5-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)
sulfamoyl]-1-methylpyrazole-4-carboxylate,
C14H18N6O7S, Mr 414.39, mp 180182
C, log
Kow 3.16, r 1.44 g/mL, pKa 3.7, vapor pressure
0.0147 mPa, consists of grayish to colorless
crystals which are moderately soluble in water,
methanol, and hexane, fairly soluble in benzene,
and acetone, and soluble in chloroform [1, 2, 83,
84].
Pyrazosulfuron-ethyl is produced by reaction
of N-1-methyl-4-carboxy-5-sulfonylisocyanate
pyrazole with 2-amino-4,6-dimethoxypyrimi-
dine [85].
Pyrazosulfuron-ethyl is a systemic herbicide
used pre- and post-emergence to control annual
and perennial broad-leaved weeds and sedges in
wet-sown and transplanted rice crops. It is ab-
sorbed by roots and leaves.
Formulation. Wettable granules, granules,
suspension concentrates.
Trade Names. Sparkstar, Sirius, Act, Billy,
Agreen, Regnet, Act.
Pyrazosulfuron-ethyl decays in soil with a
half-life of 15 d.
Rimsulfuron [122931-48-0], 1-(4,6-di-
methoxypyrimidin-2-yl)-3-(3-ethylsulfonyl-2-
Vol. 39
pyridylsulfonyl)urea, C14H17N5O7S2, Mr 431.44,
mp 176178
C, log Kow 1.46, r 1.5 g/mL, pKa
4, vapor pressure 0.89 mPa, consists of colorless
crystals which are fairly soluble in water, ethyl
acetate, and methanol, and freely soluble in
acetone and dichloromethane [1, 2, 86, 87].
Rimsulfuron is produced by reaction of 2-
sulfamoylchloride-3-sulfonylethylpyridine with
2-amino-4,6-dimethoxypyrimidine [88].
Rimsulfuron is a selective and systemic her-
bicide, absorbed by foliage and roots and trans-
located, used post-emergence to control annual
and perennial grasses and several broad-leaved
weeds in maize, potatoes and other crops. It is an
inhibitor of acetolactate synthase.
Formulation. Water-soluble granules.
Trade Name. Tarot.
Rimsulfuron decays with half-lives of 25, 12,
7 and 6 d in soil, photolytically, hydrolytically,
and in water-sediment, respectively.
Sulfometuron-methyl [74222-97-2], meth-
yl 2-(4,6-dimethylpyrimidin-2-ylcarbamoylsul-
famoyl)benzoate, C15H16N4O5S, Mr 363.38, mp
203205
C, log Kow 0.51, r 1.48 g/mL. pKa
5.2, vapor pressure 0.073 nPa, is a colorless solid
which is sparingly soluble in water, toluene, and
ethyl acetate, and fairly soluble in acetone, ace-
tonitrile, dichloromethane, and dimethyl sulfox-
ide [1, 2, 5, 89].
Sulfometuron-methyl is produced by reaction
of 2-sulfonylisocyanate methylbenzoate with 2-
amino-4,6-dimethylpyrimidine [90].
Sulfometuron-methyl is a broad-spectrum
herbicide used to control annual and perennial
grasses and broad-leaved weeds in noncropland,
as well as in forestry to control woody tree
species in pine forests. It inhibits acetolactate
synthase.
Vol. 39
Formulation. Dry flowable, solution powder.
Trade Name. Oust.
Sulfometuron-methyl decays with a half-life
of 24 d in soil. It is stable towards aqueous
hydrolysis.
Sulfosulfuron [141776-32-1], 1-(4,6-dime-
thoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo
[1,2-a]pyridin-3-ylsulfony)lurea, C16H18N6O7S2,
Mr 470.48, mp 201.1201.7
C, log Kow 0.77,
r 1.52 g/mL, pKa 3.51, vapor pressure 30.5 nPa,
is a colorless solid which is sparingly soluble
in heptane, slightly soluble in xylene, methanol,
and acetone, and moderately soluble in water
[1, 2].
Sulfosulfuron is produced by reaction of 2-
ethylsulfonylimidazo[1,2-a]pyridine 3-sulfon-
amide with 4,6-dimethoxypyrimidin-2-yl isocy-
anate [91].
Sulfosulfuron is a systemic herbicide, ab-
sorbed by roots and leaves, and translocated,
used for the control of annual grasses and
broad-leaved weeds in cereals. It acts by inhibi-
tion of acetolactate synthase.
Formulation. Wettable granules.
Trade Name. SafeGuard.
Sulfosulfuron decomposes with half-lives of
24, 35, 168, and 26 d in soil, photolytically,
hydrolytically, and in water-sediment,
respectively.
Thifensulfuron-methyl [79277-27-3], me-
thyl 3-(4-methoxy-6-methyl-1,3,5-triazin-2-ylcar-
bamoylsulfamoyl)thiophen-2-carboxylate,
C12H13N5O6S2, Mr 387.39, mp 171
C, log Kow
1.7, r 1.49 g/mL, pKa 4.4, vapor pressure 7.5
nPa, is a pale yellow liquid or consists of colorless
crystals which are slightly soluble in ethanol, and
moderately soluble in water, methanol, ethyl ace-
tate, acetone, and dichloromethane [13, 92, 93].
Weed Control, 2. Individual Herbicides 221
Thifensulfuron-methyl is produced by reac-
tion of 2-(methoxycarbonyl)-3-thiophenesulfo-
nyl isocyanate with 2-amino-4-methoxy-6-
methylpyrimidine [94].
Thifensulfuron-methyl is a selective herbi-
cide, absorbed by foliage, used post-emergence
to control grass and broad-leaved weeds in winter
and spring wheat, winter and spring barley, rye,
triticale, oats, soya beans, etc.
Formulation. Water-soluble granules, dry
flowable.
Trade Names. Pinnacle, Harald, Lancer,
Pinnacle.
Thifensulfuron-methyl decomposes with
half-lives of 4, 94, 180, and 24 d in soil, photo-
lytically, hydrolytically, and in water-sediment,
respectively.
Triasulfuron [82097-50-5], 1-[2-(2-chlor-
oethoxy)phenylsulfonyl]-3-(4-methoxy-6-meth-
yl-1,3,5-triazin-2-yl)urea, C14H16ClN5O5S, Mr
401.8, mp 188.6
C, log Kow 0.59, r 1.5 g/mL,
pKa 4.64, vapor pressure 0.0021 mPa, is a fine
colorless powder which is slightly soluble in
water and toluene, sparingly soluble in n-hexane,
moderately soluble in ethyl acetate, and soluble
in acetone and n-hexane [1, 2, 95].
Triasulfuron is produced by reaction of 2-
chloroethoxyphenylsulfamoyl chloride with 2-
amino-4-methoxy-6-methyl-1,3,5-triazine [96].
Triasulfuron is a selective herbicide used pre-
and post-emergence for the control of annual
broad-leaved weeds in wheat, barley, and
triticale.
Formulation. Wettable powders, water-dis-
persible granules.
Trade Names. Logran, Satis, Amber.
Triasulfuron decays with half-lives of 23 and
217 d in soil and water-sediment respectively. It
is stable towards aqueous photolysis and
hydrolysis.
Tribenuron-methyl [101200-48-0], methyl
2-[4-methoxy-6-methyl-1,3,5-triazin-2-yl(meth-
yl)carbamoylsulfamoyl]benzoate, C15H17N5O6S,
222 Weed Control, 2. Individual Herbicides
Mr 395.4, mp 142
C, log Kow 0.78, r 1.46 g/mL,
pKa 4.7, vapor pressure 53 nPa,is a light brown
solid with a pungent odor which is moderately
soluble in water, n-heptane, acetone, acetonitrile,
ethyl acetate, and methanol, and soluble in di-
chloromethane [13, 97, 98].
Tribenuron-methyl is produced by reaction of
methyl-2-sulfamoylchloride benzoic acid with
2-methylamino-4-methoxy-6-methyl-1,3,5-tri-
azine [99].
Tribenuron-methyl is a selective herbicide,
absorbed by foliage, used post-emergence for
the control of broad-leaved weeds in spring and
winter cereals.
Formulation. Water-dispersible granules,
dry flowable granules.
Trade Names. Express, Granstar, Pointer,
AllyMax, Calibre SX.
Tribenuron-methyl decays with half-lives of
14, 16, and 26 d in soil, hydrolytically, and in
water-sediment, respectively. It is stable towards
photolytic action.
Trifloxysulfuron-sodium [199119-58-9],
sodium N0 -(4,6-dimethoxypyrimidin-2-yl)-N-
[3-(2,2,2-trifluoromethoxy)-2-pyridylsulfonyl]
imidocarbamate, C14H13F3N5NaO6S, Mr
459.33, mp 174
C, log Kow 0.42, r
0.645 g/mL, pKa 4.76, vapor pressure
0.001 mPa, is a colorless solid which is practi-
cally insoluble in toluene, moderately soluble in
ethyl acetate, and soluble in water, acetone, and
methanol [1, 100].
Trifloxysulfuron-sodium can be prepared by
reaction of 2-sulfamoylchloride-3-(2,2,2-tri-
fluoromethoxy)pyridin with 2-amino-4,6-di-
methoxypyrimidine in the presence of a base,
Vol. 39
followed by transformation into the sodium salt
[54].
Trifloxysulfuron-sodium, absorbed by shoots
and roots and translocated, is used post-emer-
gence to control grasses, sedges, and broad-
leaved weeds in cotton, sugar cane, and other
crops. It is an acetolactate inhibitor.
Formulation. Wettable granules.
Trade Names. Brawn, Evoke.
Trifloxysulfuron-sodium decomposes with
half-lives of 63, 18, and 20 d in soil, photolyti-
cally, and hydrolytically, respectively.
Triflusulfuron-methyl [126535-15-7], meth-
yl 2-[4-dimethylamino-6-(2,2,2-trifluroethoxy)-
1,3,5-triazin-2-ylcarbamoylsulfamoyl]-m-toluate,
C17H19F3N6O6S2, Mr 492.43, mp 160163
C, log
Kow 0.96, r 1.46 g/ml, pKa 4.4, vapor pressure 0.6
nPa, is a colorless crystalline solid which is spar-
ingly soluble in hexane, slightly soluble in water,
moderately soluble in ethyl acetate and methanol,
and soluble in acetone [1, 2, 101103].
Triflusulfuron-methyl is produced by reaction
of methyl 2-sulfamoylchloride-3-methylbenzo-
ate with 2-amino-4-dimethylamino-6-(2,2,2-tri-
fluoroethoxy)-1,3,5-triazine [104].
Triflusulfuron-methyl is used post-emergence
for the control of many annual and perennial
broad-leaved weeds in sugar beet. It acts by
inhibition of amino acid biosynthesis.
Formulation. Water-dispersible granules.
Trade Names. Debut, Safari, Upbeet.
Triflusulfuron-methyl decays with half-lives
of 3, 14, and 24 d in soil, photolytically, and
hydrolytically, respectively.
Tritosulfuron [142469-14-5], 1-[4-meth-
oxy-6-(trifluoromethyl)-1,3,5-triazin-2-yl]-3-[2-
(trifluoromethyl)benzenesulfonyl]urea,
C13H9F6N5O4S, Mr 445.30, mp 167169
C, log
Kow 0.62, pKa 4.69, vapor pressure 0.01 mPa, is a
colorless solid which is slightly soluble in water
and toluene, moderately soluble in acetonitrile,
ethyl acetate, methanol, and dichloromethane,
and soluble in acetone [2, 105].
Vol. 39
Tritosulfuron can be prepared by reaction of
trifluoromethyl 2-sulfamoylchloridebenzene in
the presence of a base [54].
Tritosulfuron is a systemic, broad-spectrum
herbicide, absorbed by leaves and translocated,
used post-emergence to control a wide range of
broad-leaved weeds in cereals, maize, rice, and
turf. It acts by inhibition of acetolactate synthesis.
Formulation. Granules, water-dispersible
granules.
Trade Names. Corto, Tooler, Biathion.
Tritosulfuron decays hydrolytically with a
half-life of 70 d. In soil it has a short half-life.
1.3. Chloroacetanilides
Acetochlor [34256-82-1], 2-chloro-N-ethoxy-
methyl-60 -ethylaceto-o-toluidide, C14H20ClNO2,
Mr 269.77, mp 10.6
C, bp 172
C(7 mmHg), log
Kow 4.14, r 1.12 g/mL, vapor pressure 22 mPa, is a
wine red to yellow or amber oil with an aromatic
odor which is sparingly soluble in water and readily
soluble in diethyl ether, acetone, benzene, chloro-
form, ethanol, ethyl acetate, and toluene [13, 5,
106].
Acetochlor is produced by reaction of chlor-
oacetyl chloride with the azomethine of 2-ethyl-
6-methylaniline and formaldehyde, followed by
treatment with ethanol [107].
Acetochlor is a selective herbicide, absorbed
mainly through roots and germinating weeds,
used pre-emergence or pre-planting to control
annual grasses, certain annual broad-leaved
weeds, and yellow nutsedge in maize, peanuts,
soya beans, cotton, potatoes, and sugar cane. It
acts by lipid biosynthesis inhibition.
Formulation. Suspension concentrate, emul-
sifiable concentrate.
Trade Names. Harness,Surpass, Trophy,
Acenit.
Weed Control, 2. Individual Herbicides 223
Acetochlor decays with a half-life of 14 d in
soil. It is stable towards photolytic and hydrolytic
action.
Alachlor [15972-60-8], 2-chloro-20 ,60 -die-
thyl-N-methoxymethylacetanilide, C14H20ClNO2,
Mr 269.77, mp 40.541.5
C, bp 100
C, log Kow
3.09, r 1.13 g/mL, vapor pressure 2.9 mPa, is a
yellow to wine red colored solid which is sparingly
soluble in water, n-hexane, readily soluble in
diethyl ether, acetone, benzene, chloroform, etha-
nol, and ethyl acetate [13, 108110].
Alachlor is synthesized by reaction of chlor-
oacetyl chloride with the azomethine of 2,6-
diethylaniline and formaldehyde, followed by
treatment with methanol [107].
Alachlor is a selective, systemic herbicide,
absorbed by germinating roots, used pre-emer-
gence to control annual grasses and many broad-
leaved weeds in cotton, brassicas, maize, oil-
seed rape, peanuts, etc. It inhibits lipid
biosynthesis.
Formulation. Granules, emulsifiable concen-
trate, dry formulation.
Trade Names. Lasso, Alanox, Lacorn,
Satochlor.
Alachlor decays with half-lives of 14, 0.5, 0.5,
and 2 d in soil, photolytically, hydrolytically,
and in water-sediment, respectively.
Butachlor [23184-66-9], N-butoxymethyl-
2-chloro-20 ,60 -diethylacetanilide, C17H26NO2,
Mr 311.9, mp 2.8 to 1.7
C, bp 156
C(66.5
Pa), log Kow 4.5, r 1.08 g/mL, vapor pressure
0.24 mPa, is a light yellow to purple colored
liquid with a faint sweet odor which is sparingly
soluble in water, readily soluble in most organic
solvents [13].
Butachlor is produced by reaction of chlor-
oacetyl chloride with the azomethine of 2,6-
224 Weed Control, 2. Individual Herbicides
diethylaniline and formaldehyde, followed by
treatment with n-butanol [107].
Butachlor is a selective systemic herbicide,
absorbed primarily by germinating shoots,used
pre-emergence for the control of annual grasses
and certain broad-leaved weeds in seeded and
transplanted rice. It acts by inhibition of mitosis
and cell division.
Formulation. Emulsifiable concentrate,
granules.
Trade Names. Machete, Butataf, Butanex,
Formachlor, Weedout.
Butachlor decays with half-lives of 56, 1.2
and12 d in soil, hydrolytically, and by biodegra-
dation, respectively.
Diethatyl-ethyl [38727-55-8], N-chloroace-
tyl-N-(2,6-diethylphenyl)glycine, C16H22ClNO3,
Mr 311.80, mp 4950
C, bp 448
C at 101 kPa, r
1.15 g/mL, vapor pressure 0.43 mPa, is a color-
less crystalline solid which is sparingly soluble in
water, and soluble in many organic solvents
[111].
Diethatyl-ethyl can be made by reaction of
2,6-diethylaniline with chloroacetic acid in the
presence of a base, followed by hydrogenation of
the imine and reaction with chloroacetyl chloride
[112].
Diethatyl-ethyl is a selective herbicide
used pre-emergence to control many annual
grasses and some broad-leaved weeds in some
crops.
Formulation. Emulsifiable concentrate.
Trade Name. Antor, Hercules, Bay NNT
6867.
Diethatyl-ethyl decays in soil with a half-life
of 30 d.
Dimethachlor [50563-36-5], 2-chloro-N-(2-
methoxyethyl)aceto-20 ,60 -xylidide, C13H18ClNO2,
Mr 255.74, mp 45.846.7
C, log Kow 2.17, r
1.23 g/mL, vapor pressure 0.64 mPa, forms color-
less crystals which are fairly soluble in water, and
readily soluble in methanol, acetone, octanol, and
hexane [1, 2, 113, 114].
Vol. 39
Dimethachlor is produced by reaction of 2,6-
dimethylaniline with a-chloroethylmethyl ether,
followed by reaction with chloroacetyl chloride
[115].
Dimethachlor is a selective soil herbicide,
absorbed by new shoots of seedlings and roots,
used pre-emergence for the control of annual
grasses and broad-leaved weeds in oilseed rape.
Formulation. Emulsifiable concentrate.
Trade Name. Teridox.
Dimethachlor decomposes with half-lives of
7, 200, and 14 d in soil, hydrolytically, and in
water-sediment, respectively. It is stable towards
photolytic action.
Metazachlor [67129-08-2], 2-chloro-N-
(pyra-zol-1-ylmethyl)acet-20 ,60 -xylidide,
C14H16ClN3O, Mr 277.75, mp 85
C, log Kow
2.49, r 1.31 g/mL, vapor pressure 0.093 mPa,
consists of yellowish to colorless crystals which
are moderately soluble in water, and readily
soluble in hexane, toluene, dichloromethane,
acetone, chloroform, ethyl acetate, and ethanol
[1, 2, 116, 117].
Metazachlor is produced by reaction of 2,6-
dimethylaniline with formaldehyde, followed by
treatment with chloroacetyl chloride, and then
with potassium pyrazole [118].
Metazachlor is a selective herbicide used pre-
and early post-emergence for the control of
winter and annual grasses and broad-leaved
weeds in a variety of crops. It inhibits ergosterol
biosynthesis.
Formulation. Suspension concentrate.
Trade Names. Butisan S, Nimbus, Rapsan,
Shadow, Sultan.
Metazachlor decays with half-lives of 77 and
21 d in soil and water-sediment, respectively. It
is stable towards photolytic and hydrolytic
action.
Vol. 39
S-Metolachlor [87392-12-9]/[178961-20-
1], mixture of 80-100% 2-chloro-N-(6-ethyl-o-
tolyl)-N-[(1S)-2-methoxy-1-methylethyl]acet-
amide and 200% 2-chloro-N-(6-ethyl-o-tolyl)-
N-[(1R)-2-methoyy-1-methylethyl]acetamide,
C15H22ClNO2, Mr 283.79, mp62.1
C, bp
100
C (0.133 Pa), log Kow 3.05, r 1.12 g/mL,
vapor pressure 3.7 mPa, is a colorless to light tan
liquid which is sparingly soluble in water, and
miscible with acetone, methanol, toluene, and n-
hexane [13, 5, 119].
S-Metolachlor is produced by reaction of 2-
methyl-6-ethylanilin with 2-chloroisopropyl
methyl ether, followed by treatment with chlor-
oacetyl chloride [120].
S-Metolachlor is a selective herbicide, ab-
sorbed by roots and shoots, used pre-emergence
and is incorporated pre-planting to control annual
grasses and some annual broad-leaved weeds in
many crops.
Formulation. Emulsifiable concentrate,
granules, suspension concentrate.
Trade Names. Dual, Dual S, Dual II, Bicep,
Primagram.
S-Metolachlor decomposes in soil and water-
sediment with half-lives of 90 and 365 d, respec-
tively. It is stable towards photolytic and hydro-
lytic action.
Pretilachlor [51218-49-6], 2-chloro-
20 ,60 -diethyl-N-(2-propoxyethyl)acetanilide,
C17H26ClNO2, Mr 311.85, bp 135
C (0.133 Pa),
log Kow 4.08, r 1.08 g/mL, vapor pressure
0.133 mPa, is a colorless liquid which is spar-
ingly soluble in water,and readily soluble in
benzene, hexane, methanol, and dichloro-
methane [1, 2].
Pretilachlor is produced by reaction of 2,6-
diethylamine with a-chloroethyl propyl ether, fol-
lowed by reaction with chloroacetyl chloride [121].
Weed Control, 2. Individual Herbicides 225
Pretilachlor is a selective herbicide effective
against the main annual grasses, broad-leaved
weeds, and sledges in transplanted and seeded
rice. It inhibits cell division and mitosis.
Formulation. Emulsifiable concentrate,
granules.
Trade Names. Rifit, Sofit, Solnet, Gorbo,
Sparkstar.
Pretilachlor decays in soil with a half-life of
30 d. It is stable against hydrolytic action.
Propachlor [1918-16-7], 2-chloro-N-iso-
propylacetanilide, C11H14ClNO, Mr 211.69, mp
77
C, bp 110
C (2.99 Pa, log Kow 2.18, r
1.242 g/mL, vapor pressure 98.4 mPa, is a light
tan colored solid which is sparingly soluble in
water, and readily soluble in acetone, xylene,
toluene, benzene, and other organic solvents
[13, 122124].
Propachlor is produced by reaction of aniline
with 2-chloroisopropane, followed by treatment
with chloroacetyl chloride [125].
Propachlor is a selective herbicide used pre-
emergence and pre-planting-incorporated to con-
trol annual grasses and some broad-leaved weeds
in a range of crops. It acts by interfering with
protein synthesis.
Formulation. Granules, wettable powder,
suspension concentrate.
Trade Names. Ramrod, Albrass, Satecid,
Prolex, Ashlade.
Propachlor decomposes with half-lives of 5,
18, 28 and 84 d in soil, photolytically, hydrolyti-
cally, and in water-sediment, respectively.
Propisochlor [86763-47-5], 2-chloro-60 -
ethyl-N-isopropoxymethylacetotoluidide,
C15H22ClNO2, Mr 283.80 mp 21.6
C, bp 243
C
(decomp.), log Kow 3.5, r 1.1 g/mL, vapor pres-
sure 4.0 mPa, is a light brown to purple oil which
is sparingly soluble in water,and soluble in most
organic solvents [1, 2].
226 Weed Control, 2. Individual Herbicides
Propisochlor is produced by reaction of 2-
methyl-6-ethylaniline with chloromethyl isopro-
pyl ether, followed by reaction with chloroacetyl
chloride [126].
Propisochlor is a selective herbicide used pre-
emergence and pre-planting-incorporated for the
control of annual grasses and some broad-leaved
weeds in maize, sunflowers, soya beans, pota-
toes, and peas. It interferes with protein
biosynthesis.
Formulation. Technical, emulsifiable con-
centrate.
Trade Name. Proponit.
Propisochlor decays with a half-life of 13 d in
soil. It is stable towards hydrolytic action.
Thenylchlor [96491-05-3], 2-chloro-N-(3-
methoxy-2-thenyl)-20 ,60 -dimethylacetanilide,
C16H18ClNO2S, Mr 324.84, mp 7274
C, log
Kow 3.53, r 1.19 g/mL, vapor pressure
0.028 mPa, is a colorless solid which is sparingly
soluble in water, and soluble in many organic
solvents [13].
Thenylchlor is produced by reaction of 2,6-
dimethylaniline with 3-methoxy-2-thenylmethyl
chloride, followed by treatment with chloroace-
tyl chloride [127].
Thenylchlor is used pre-emergence for the
control of annual grasses and broad-leaved
weeds in paddy rice. It is absorbed through roots
and inhibits protein biosynthesis.
Formulation. Emulsifiable concentrate.
Trade Names. Kusamets, Onebest.
Thenylchlor decays in soil with a half-life of
14 d.
1.4. 1,3,5-Triazines
Ametryn [834-12-8], N2-ethyl-N4-iso-
propyl-6-methylthio-1,3,5-triazine-2,4-diamine,
C9H17N5S, Mr 227.33, mp 8486
C, bp 345
C,
log Kow 2.63, r 1.18 g/mL, pKa 10.07, vapor
pressure 0.365 mPa, is a colorless powder which
is slightly soluble in water, moderately soluble in
Vol. 39
n-hexane and toluene, and readily soluble in
acetone, methanol, and n-octanol [13, 128].
Ametryn is produced by reaction of atrazine
with methyl mercaptan in the presence of sodium
hydroxide [129].
Ametryn is a selective, systemic herbicide
used pre- and post-emergence for the control of
most annual grasses and broad-leaved weeds in
pineapples, sugar cane, bananas, citrus fruit,
maize, coffee, tea, etc, and in noncropland.
Formulation. Water-dispersible granules,
dry flowable, wettable powder, suspension
concentrate.
Trade Names. Evik, Gesapax, Mebatryne,
Amesip.
Ametryn decays with a half-life of 37 d in soil.
It is stable towards hydrolysis.
Atrazine [1912-24-9], 6-chloro-N2-ethyl-N4-
isopropyl-1,3,5-triazine-2,4-diamine, C8H14ClN5,
Mr 215.68, mp 175.178
C, log Kow 2.7., r
1.23 g/mL, pKa 1.7, vapor pressure 0.039 mPa,
forms a colorless powder which is sparingly soluble
in water and n-hexane, fairly soluble in toluene, and
n-octanol, and readily soluble in ethyl acetate,
acetone, dichloromethane, and ethanol [13,
130132].
Atrazine is produced by reaction of cyanuric
chloride with one equivalent of ethylamine, fol-
lowed by treatment with one equivalent of iso-
propylamine [133].
Atrazine is a selective, systemic herbicide
with residual and foliar activity used pre- and
post-emergence to control annual broad-leaved
weeds and annual grasses in maize, sorghum,
sugar cane, etc, and in industrial weed control. Its
use is restricted. It inhibits photosystem II.
Formulation. Suspension concentrate,
wettable powder, water-dispersible granules,
flowable.
Vol. 39
Trade Names. Atrex, Bicep, Gesaprim, Pri-
magram, Primextra, Mebazine, Vectal, Atratol,
Primatol, Fenamin, Atrazinax.
Atrazine decomposes with half-lives of 75,
2.6, 86, and 86 d in soil, photolytically, hydro-
lytically, and in water-sediment, respectively.
Cyanazine [21725-46-2], 2-(4-chloro-6-
ethylamino-1,3,5-triazin-2-ylamino)-2-methyl-
propiononitrile, C9H13ClN6, Mr 240.69, mp 167
168
C, log Kow 2.1, r 1.29 g/mL, pKa 12.9,
vapor pressure 0.213 mPa, is a colorless crystal-
line solid which is moderately soluble in water,
fairly soluble in benzene and carbon tetrachlo-
ride, and readily soluble in chloroform, acetone,
and ethanol [13].
Cyanazine is produced by successive reaction
of cyanuric chloride with ethylamine and 2-
methyl-2-cyanopropylamine [134].
Cyanazine is a selective, systemic herbicide
with contact and residual activity used pre-emer-
gence for general weed control. It inhibits pho-
tosystem II.
Formulation. Granules, wettable powder,
emulsion concentrate.
Trade Names. Bladex, Cy-Pro, Payze,
Fortrol.
Cyanazine decays with half-lives of 16 and
84 d in soil and water-sediment, respectively. It
is stable towards photolysis and hydrolysis.
Cyprazine [22936-86-3], 6-chloro-N2-
4
cyclopropyl-N -isopropyl-1,3,5,-triazine-2,4-di-
amine, C9H14ClN5, Mr 227.7, mp 167
C, log Kow
3.06, r 1.25 g/mL, vapor pressure 39.9 mPa, forms
colorless crystals which are sparingly soluble in
water, moderately soluble in n-hexane, and soluble
in acetonitrile, toluene, benzene, dimethylforma-
mide, ethyl acetate, and chloroform [3].
Weed Control, 2. Individual Herbicides 227
Cyprazine can be prepared by reaction of
cyanuric acid with cyclopropylamine and iso-
propylamine in the presence of a base. [3].
Cyprazine is an herbicide used post-emer-
gence against broad-leaved weeds and grasses.
Formulation. Wettable powder, emulsifiable
concentrate.
Trade Names. Outfox, Prefox.
Cyprazine is biodegraded and hydrolysed with
half-lives of 70 and about 200 d, respectively.
Desmetryn [1014-69-3], N2-isopropyl-N4-
methyl-6-methylthio-1,3,5-triazine-2,4-diamine,
C8H15N5S, Mr 213.30, mp 8486
C, bp 339 (98.4
kPa), log Kow 2.38, r 1.18 g/mL, pKa 4, vapor
pressure 0.13 mPa, is a colorless powder which is
sparingly soluble in water, and readily soluble in
most organic solvents [13].
Desmetryn is produced by reaction of cyanu-
ric chloride with, in turn, isopropylamine, me-
thylamine, and methanethiol [133].
Desmetryn is a selective systemic herbicide,
absorbed by leaves and roots, used post-emer-
gence for the control of fat-hen and other annual
broad-leaved weeds and grasses in brassica,
herbs, onions, leeks, and conifer seedbeds. It
inhibits photosynthesis.
Formulation. Wettable powder.
Trade Name. Semeron.
Desmetryn decomposes with half-lives of 9
and 34 d in soil and water-sediment, respective-
ly. It is stable towards hydrolysis.
Dimethametryn [22936-75-0], (RS)-N2-
(1,2-dimethylpropyl)-N4-ethyl-6-methylthio-
1,3,5-triazine-2,4-diamine, C11H21N5S, Mr
255.38, mp 65
C, bp 151
C, log Kow 3.90, r
1.11 g/mL, forms colorless crystals which are
sparingly soluble in water, and readily soluble in
acetone, dichloromethane, methanol, n-octanol,
hexane, and toluene [1, 2].
228 Weed Control, 2. Individual Herbicides
Dimethametryn is produced by reaction of
cyanuric chloride with ethylamine, followed by
treatment with isobutylamine [135].
Dimethametryn is a selective herbicide, ab-
sorbed by roots and foliage, used for the control
of annual broad-leaved weeds in transplanted-
and seeded rice.
Formulation. Wettable powder.
Trade Names. Avirosan, Sparkstar.
Dimethametryn is stable against hydrolytic
action.
Indaziflam [950782-86-2], N-[(1R,2S)-2,3-
dihydro-2,6-dimethyl-1H-inden-1-yl]-6-[(1RS)-
1-fluoroethyl]-1,3,5-triazine-2,4-diamine,
C16H20FN5, Mr 301.30 [136].
Indaziflam can be made by reaction of 6-(1-
fluoroethyl)-1,3,5-triazine-2,4-diamine with 6-
chloro-2,3-dihydro-2,6-dimethyl-1H-indene in
the presence of a base [54].
Indaziflam is a new herbicide intended for use
on turf and orchard crops.
Methoprotryn [841-06-5], N2-isopropyl-
4 Trade Names. Pramitol, Ontrack.
N -(3-methoxypropyl)-6-methylthio-1,3,5-tri-
azine-2,4-diamine, C11H21N5OS, Mr 271.39, mp
6869
C, log Kow 2.82, r 1.186 g/mL, pKa 4.0,
vapor pressure 0.038 mPa, is a crystalline solid
which is sparingly soluble in water, moderately
soluble in hexane, and soluble in acetone, di-
chloromethane, methanol, and toluene [2, 3].
Methoprotryn can be synthesized by reaction
of 2-chloro-4-isopropylamino-6-(3-methoxy-
propylamino)-1,3,5-triazine with methyl mer-
captan in the presence of alkali [3].
Methoprotryn is used post-emergence for the
effective control of grass weeds in winter and
summer cereals. It inhibits photosynthesis.
Vol. 39
Formulation. Wettable powder.
Trade Name. Gesaran.
Methprotryn is degraded with a half-life of 2.4
hours in the atmosphere.
Prometon [1610-18-0], N2,N4-diisopropyl-6-
methoxy-1,3,5-triazine-2,4-diamine, C10H19N5O,
Mr 225.3, mp 9192
C, log Kow 2.91, r
1.088 g/mL, pKa 4.3, vapor pressure 0.306 mPa,
is a colorless powder which is slightly soluble
in water, readily soluble in benzene, methanol,
acetone, dichloromethane, and toluene [13,
137].
Prometon is produced by reaction of propa-
zine with methanol in the presence of sodium
hydroxide [129].
Prometon is a nonselective, systemic herbi-
cide, absorbed by foliage and roots, which is used
to control most annual and many perennial
broad-leaved weeds, grasses, and brush weeds
on non-crop areas. It is an inhibitor of
photosynthesis.
Formulation. Granules, emulsifiable concen-
trate, pellets, wettable powder.
Prometon decays in soil with a half-life of
500 d. It is stable towards hydrolysis.
Prometryn [7287-19-6], N2,N4-diisopro-
pyl-6-methylthio-1,3,4-triazine-2,4-diamine,
C10H19N5S, Mr 214.36, mp 118120
C, log Kow
3.34, r 1.15 g/mL, pKa 4.05, vapor pressure
0.13 mPa, is a colorless crystalline powder
which is sparingly soluble in water, fairly soluble
in hexane, and readily soluble in acetone, etha-
nol, methanol, toluene, and n-octanol [13].
Prometryn is produced by reaction of propa-
zine with methyl mercaptan in the presence of
Vol. 39
sodium hydroxide, followed by treatment with
dimethyl sulfate [129].
Prometryn is a selective, systemic herbicide
with residual and contact activity used pre-emer-
gence to control annual grasses and broad-leaved
weeds in cotton, sunflowers, peanuts, cereals,
peas, and beans and used post-emergence in
cotton, potatoes, carrots, celery, and leeks.
Formulation. Wettable powder, suspension
concentrate, water-dispersible granules, emulsi-
fiable concentrate.
Trade Names. Caparol, Gesagard, Cotton-
Pro, Efmetryn, Gewan, Suprend.
Prometryn decays with half-lives of 41, 30,
and 38 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
Propazine [139-40-2], 6-chloro-N2,N4-dii-
sopropyl-1,3,5-triazine-2,4-diamine, C9H16ClN5,
Mr 129.71, mp 212214
C, log Kow 3.95, r
1.16 g/mL, pKa 1.7, vapor pressure 0.004 mPa,
is a colorless crystalline powder which is slightly
soluble in water, fairly soluble in benzene, tolu-
ene, diethyl ether, and carbon tetrachloride [13,
5, 138].
Propazine is produced by the reaction be-
tween cyanuric chloride and two equivalents of
isopropylamine [139].
Propazine is a selective, systemic herbicide
used pre-planting and pre-emergence for the
control of annual grasses and broad-leaved
weeds in sorghum and umbelliferous crops.
Formulation. Wettable powder, water-dis-
persible granules, emulsifiable concentrate.
Trade Names. Gesamil, Milogard, Milo-Pro,
Caswell, Max90.
Propazine decomposes with half-lives of 131,
0.8, 83 and 77 d in soil, photolytically, hydrolyt-
ically, and in water-sediment, respectively.
Simazine [122-34-9], 6-chloro-N2,N4-
diethyl-1,3,5-triazine-2,4-diamine, C7H12ClN5,
Mr 201.66, mp 225227
C, log Kow 2.3, r
1.3 g/mL, pKa 1.67, vapor pressure 0.00081 mPa,
Weed Control, 2. Individual Herbicides 229
is a colorless powder which is slightly soluble in
water and n-hexane, and moderately soluble in
ethanol, acetone, toluene, and n-octanol [13,
140, 141].
Simazine is produced by reaction of cyanuric
chloride with two equivalents of ethylamine
[142].
Simazine is a selective, systemic, soil-acting
herbicide used for the control of most germinat-
ing annual grasses and broad-leaved weeds in
many crops. It inhibits photosystem II.
Formulation. Granules, pellets, wettable
powder, suspension concentrate, water-dispers-
ible granules.
Trade Names. Caliber, Gesatop, Princep,
Princep Caliber, Amizina, Sanasim, Drexel.
Simazine decays with half-lives of 60, 1.9, 96,
and 33 d in soil, photolytically, hydrolytically,
and in water-sediment.
Simetryn [1014-70-6], N2,N4-diethyl-6-
methylthio-1,3,5-triazine-2,4-diamine, C8H15N5S,
Mr 213.30, mp 8283
C, log Kow 2.8, pKa 4.0,
consists of colorless crystals which are sparingly
soluble in water, moderately soluble in n-hexane,
and readily soluble in methanol, acetone, and
toluene [1, 2].
Simetryn is produced by reaction between
simazine and methanethiol [129].
Simetryn is a selective, systemic herbicide
used in combination with thiobencarb to control
broad-leaved weeds in rice, corn, soybean,
wheat, and cotton.
Formulation. Granules.Trade Name. Gy-bon.
Simetryn decomposes in soil with a half-life
of 60 d.
Terbumeton [33693-04-8], N2-tert-butyl-
4
N -ethyl-6-methoxy-1,3,5-triazine-2,4-diamine,
C10H19N5O, Mr 225.29, mp 123124
C, log Kow
230 Weed Control, 2. Individual Herbicides
3.04, r 1.08 g/mL, vapor pressure 0.27 mPa,
forms colorless crystals which are sparingly sol-
uble in water, moderately soluble in n-octanol,
and readily soluble in acetone, toluene, metha-
nol, dichloromethane, and n-hexane [1, 2].
Terbumeton is produced by reaction of 2-tert-
butylamino-4-chloro-6-ethylamino-s-triazine
with methanol and sodium hydroxide [129].
Terbumeton is a selective herbicide, absorbed
by leaves and roots, used to control annual and
perennial grasses and broad-leaved weeds in
citrus orchards. In combination with terbuthyla-
zine, is used for herbicidal control in vineyards,
apple, and citrus orchards, and in forestry.
Formulation. Wettable powder.
Trade Name. Caragard.
Terbumeton decays in soil with a half-life of
300 d.
Terbuthylazine [5915-41-3], N2-tert-butyl-
6-chloro-N4-ethyl-1,3,5-triazine-2,4-diamine,
C9H16ClN5, Mr 229.71, mp 176179
C, log Kow
3.4, r 1.1.9 g/mL, pKa 2, vapor pressure
0.15 mPa, is a colorless powder which is slightly
soluble in water, fairly soluble in acetone, etha-
nol, and n-octanol, and soluble in toluene [13].
Terbuthylazine is produced by reaction of
cyanuric chloride with tert-butylamine, followed
by treatment with ethylamine in the presence of
sodium hydroxide [143].
Terbuthylazine is a broad-spectrum herbicide
with strong and rapid effects used pre- and post-
emergence for the control of broad-leaved weeds
in many crops, in forestry, and in tree nurseries.
Formulation. Suspension concentrate, emul-
sifiable concentrate.
Trade Names. Gardoprim, Folar, Topogard,
Tyllanex, Calaris, Skirmish.
Terbuthylazine decays with half-lives of 77
and 70 d in soil and water-sediment, respective-
Vol. 39
ly. It is stable towards photolytic and hydrolytic
action.
Terbutryn [886-50-0], N2-tert-butyl-N4-
ethyl-6-methylthio-1,3,5-triazine-2,4-diamine,
Cl0Hl9N5S, Mr 241.36, mp 104105
C, bp
160
C (7.98 Pa), log Kow 3.65, r 1.12 g/mL,
pKa 4.3, vapor pressure 0.225, is a colorless
crystalline powder which is slightly soluble in
water, moderately soluble in hexane, and soluble
in acetone, n-octanol, and methanol [13, 5].
Terbutryn is produced by reaction of 2-chloro-
4-ethylamino-4,6-butylamino-1,3,5-triazine with
methyl mercaptan in the presence of sodium
hydroxide [129].
Terbutryn is a selective herbicide, absorbed
by roots and foliage and translocated, used pre-
emergence as well as post-emergence to control
black grass and annual meadow grass in winter
cereals, sugar cane, sunflowers, and other crops.
Formulation. Wettable powder, suspension
concentrate.
Trade Names. Igran, Terbutrex, Igrator,
Plantomit, Short-Stop.
Terbutryn decomposes with half-lives of 74,
0.5, and 60 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
Triaziflam [131475-57-5], (RS)-N-[2-(3,5-
dimethylphenoxy)-1-methylethyl]-6-(1-fluoro-
1-methylethyl)-1,3,5-triazine-2,4-diamine,
C17H24FN5O, Mr 333.40, bp 540
C (101 kPa), r
1.187 g/mL, is a viscous material [144].
Triaziflam can be synthesized by reaction of
6-(1-fluoro-1-methyllethyl)-1,3,5-triazine-2,4-
diamine with 3,5-dimethyl-(2-chloro)isopropyl-
phenolate [145].
Vol. 39
Triaziflam is used pre- and post-emergence to
control broad-leaved weeds and some grasses in
rice, turf, and other crops. It inhibits electron flow
in photosystem II, and also inhibits cell division.
Formulation. Wettable powder, suspension
concentrate.
Trade Name. IDH-1105.
Trietazine [1912-26-1], 6-chloro-N2,N2,N4-
triethyl-1,3,5-triazine-2,4-diamine, C9H16ClN5,
Mr 229.71, mp 102103
C, log Kow 3.34, r
1.22 g/mL, pKa 1.88, vapor pressure 8.97 mPa,
consists of colorless crystals which are sparingly
soluble in water, and readily soluble in acetone,
benzene, chloroform, dioxane, and ethanol [1, 2].
Trietazine is produced by reaction of tri-
chloro-1,3,5-triazine with ethylamine, followed
by treatment with diethylamine [146].
Trietazine is a selective herbicide, absorbed
through roots and leaves, used for weed control in
combination with linuron in potatoes, in combi-
nation with simazine in peas, and in combination
with terbutryn in potatoes, peas, and field beans.
It is a photosystem II inhibitor.
Formulation. Suspension concentrate, wetta-
ble powder.
Trade Names. Remtal, Aventox.
Trietazine decays in soil with a half-life of 60 d.
1.5. Ureas
Chlorbromuron [13360-45-7], 3-(4-bromo-
3-chlorophenyl)-1-methoxy-1-methylurea,
C9H10BrClN2O2, Mr 293.57, mp 9597
C, log
Kow 3.09, r 1.69 g/mL, vapor pressure 0.053 mPa,
is a colorless powder which is sparingly soluble in
water, moderately soluble in hexane and benzene,
and readily soluble in acetone, dichloromethane,
and isopropyl alcohol [13].
Weed Control, 2. Individual Herbicides 231
Chlorbromuron is made by bromination of N-
(3-chlorophenyl)-N0 -methoxy-N0 -methyl urea
[147].
Chlorbromuron is a selective herbicide, ab-
sorbed by roots and translocated, used pre-emer-
gence on carrots, peas, potatoes, sugar cane, and
sunflowers; is used post-emergence on carrots
and transplanted celery.
Formulation. Wettable powder, granules.
Trade Names. Maloran, Bromex.
Chlorbromuron decomposes in soil and wa-
ter-sediment with half-lives of 39 and 52 d,
respectively.
Chlorotoluron [15545-48-9], 3-(3-chloro-
p-tolyl)-1,1-dimethylurea, C10H13ClN2O, Mr
212.68, mp 148.1
C, log Kow 2.5, r 1.34 g/mL,
vapor pressure 0.005 mPa, is a colorless crystal-
line powder which is slightly soluble in water and
hexane, moderately soluble in toluene, and solu-
ble in acetone, dichloromethane, ethanol, n-oc-
tanol, and ethyl acetate [13].
Chlorotoluron is produced by reaction of 3-
chloro-p-tolyl isocyanate with dimethylamine
[148].
Chlorotoluron is a selective, nonsystemic her-
bicide, absorbed by roots and foliage, used as a
residual soil-acting herbicide and as a contact
foliar spray against many broad-leaved weeds
and grass weeds of winter cereals. It inhibits
photosynthetic electron transport.
Formulation. Suspension concentrate, wetta-
ble powder, wettable granules.
Trade Names. Dicuran, Cekutoluron, Tolu-
gan Extra, Tolerate.
Chlorotoluron decays with half-lives of 45,
0.12, and 352 d in soil, photolytically, and in
water-sediment, respectively. It is stable towards
aqueous hydrolysis.
Chloroxuron [1982-47-4], 3-[4-(4-chlorophe-
noxy)phenyl]-N,N-dimethylurea, C15H15ClN2O2,
Mr 290.75, mp 151 152
C, log Kow 3.4, r
1.34 g/mL, vapor pressure 0.23mPa, is a colorless
solid which is sparingly soluble in water, moderately
soluble in toluene, and soluble in acetone, dichloro-
232 Weed Control, 2. Individual Herbicides
methane, chloroform, dimethylformamide [13].
Chloroxuron can be made by reaction of
phosgene with p-chlorophenoxyaniline to give
4-(40 -chlorophenoxy)phenyl isocyanate, which
is treated with dimethylamine [3].
Chloroxuron is a selective herbicide, absorbed
by roots and leaves, used pre-emergence to con-
trol annual grasses and broad-leaved weeds in
peas, beans, carrots, celery, onions, leeks, and
others. It is a growth inhibitor.
Formulation. Wettable powder.
Trade Names. Tenoran, Chlorphencarb, Nor-
ex, C-1933.
Chloroxuron decomposes with half-lives of
36, 0.015, and 2896 d in soil, photolytically, and
hydrolytically, respectively.
Cumyluron [99485-76-4], 1-(2-chloroben-
zyl)-3-(1-methyl-1-phenylethyl)urea,
C17H19ClN2O, Mr 302.79, mp 166167
C, bp
503
C (101 kPa), r 1.164 g/mL, vapor pressure
0.133 mPa, is a colorless solid which is practi-
cally insoluble in water, sparingly soluble in
xylene and hexane, and moderately soluble in
benzene, soluble in acetone, methanol [149,
150].
Cumyluron can be made by reaction of 1-
chlorobenzyl isocyanate with 1-methyl-1-phen-
ylethylamine in the presence of a base [54].
Cumyluron is used on weeds and grasses in
rice and turf.
Formulation. Granules, suspension con-
centrate.
Trade Names. Kumiron, Jumbo Halm.
Cycluron [2163-69-1], 3-cyclooctyl-1,1-
dimethylurea, C11H22N2O, Mr 198.35, mp
138
C, log Kow 2.84, r 0.97 g/mL, vapor pres-
Vol. 39
sure 8.89 mPa, is a colorless crystalline product
which is moderately soluble in water, and soluble
in acetone, benzene, methanol, and ethyl acetate
[2, 3].
Cycluron can be prepared by reaction of cy-
clooctylamine with dimethylcarbamoyl chloride
[3].
Cycluron is absorbed by roots and used pre-
emergence to control weeds and grasses in peas,
beans, and spinach. It inhibits photosystem II.
Formulation. Emulsion concentrate.
Trade Name. Alipur.
Cycluron decays with half-lives of 15 h and
4.560 weeks in the atmosphere and in soil,
respectively.
Daimuron [42609-52-9], 1-(1-methyl-1-
phenylethyl)-3-p-tolylurea, C17H20N2O, Mr
268.4, mp 203
C, r 1.108 g/ml, vapor pressure
453 nPa, forms colorless needles which are spar-
ingly soluble in water, hexane and benzene, and
moderately soluble in acetone and methanol [13].
Daimuron is produced by reaction of isopro-
pylaniline with p-toluene isocyanate [151].
Daimuron is a selective herbicide, mainly
absorbed by roots, with rapid translocation, used
pre- and post-emergence to control cyperaceous
weeds and annual grass weeds in paddy rice. It
inhibits cell division.
Formulation. Wettable powder, granules.
Trade Name. Showrone.
Daimuron decays with a half-life of 50 d in
soil.
Dimefuron [34205-21-5], 3-[4-(5-tert-bu-
tyl-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl)-3-
chlorophenyl]-1,1-dimethylurea, C15H19ClN4O3,
Mr 338.79, mp 193
C, log Kow 2.51, r 1.3 g/mL,
vapor pressure 0.01 mPa, consists of colorless
crystals which are slightly soluble in water, ben-
zene, toluene, and xylene, readily soluble in
Vol. 39
chloroform, and moderately soluble in acetone,
acetonitrile, and ethanol [13].
Dimefuron is produced by the reduction of the
nitro group in 4-(5-tert-butyl-2,5-dihydro-2-oxo-
1-oxadiazol-3-yl)-3-chloronitrobenzene, fol-
lowed by treatment with phosgene and then with
dimethylamine [152].
Dimefuron is a selective herbicide, absorbed
mainly by roots, used pre-and post-emergence
against different annual broad-leaved weeds in
many crops. It inhibits photosystem II
Formulation. Wettable powder.
Trade Names. Pradone, Scorpion.
Dimefuron decomposes with half-lives of 65,
226, and 97 d in soil, hydrolytically, and in
water-sediment, respectively.
Diuron [330-54-1], 3-(3,4-dichlorophenyl)-
1,1-dimethylurea, C9H10Cl2N2O, Mr 233.09, mp
158159
C, bp 180190
C (decomp.), log Kow
2.87, r 1.5 g/mL, vapor pressure 1.15 mPa, forms
colorless crystals which are slightly soluble in
water, moderately soluble in hydrocarbons, fairly
soluble in acetone, ethyl acetate, and benzene
[13, 153].
Diuron is produced by reaction of 3,4-di-
chlorophenyl isocyanate with dimethylamine
[154].
Diuron is a systemic herbicide, absorbed by
roots, used to control weeds and mosses on
noncrop areas and is used for selective control
of germinating grass and broad-leaved weeds in
many crops. It inhibits photosynthesis.
Formulation. Wettable powder, suspension
concentrate, granules.
Trade Names. Karmex, Seduron, Toterbane,
Divide, Diurex, Freeway.
Diuron decays with half-lives of 76, 43, and
48 d in soil, photolytically, and in water-sedi-
Weed Control, 2. Individual Herbicides 233
ment, respectively. It is stable towards hydrolytic
action.
Fenuron [101-42-8], 1,1-dimethyl-3-phe-
nylurea, C9H12N2O, Mr 164.20, mp 133134
C,
log Kow 0.98, r 1.08 g/mL, vapor pressure
5 mPa, consists of colorless crystals which are
moderately soluble in water, diethyl ether, ace-
tone, and benzene, and readily soluble in ethanol,
acetone, and chloroform [13].
Fenuron is produced by reaction of phenyl
isocyanate with dimethylamine [154].
Fenuron is a nonselective, systemic herbicide
used pre-emergence for the control of woody
plants and deep-rooted perennial broad-leaved
weeds on noncropland. It inhibits photosynthesis.
Formulation. Wettable powder.
Trade Names. Croptex Chrome, Beet-Kleen,
Croptex Ruby.
Fenuron decays with a half-life of 60 d in soil.
Fluometuron [2164-17-2], 1,1-dimethyl-3-
(a,a,a-trifluoro-m-tolyl)urea, C10H11F3N2O, Mr
232.3, mp 163164
C, log Kow 2.38, r 1.39 g/
mL, vapor pressure 0.125 mPa, consists of col-
orless crystals which are slightly soluble in water
and hexane, moderately in xylene and n-octanol,
and soluble in dichloromethane,n-octanol meth-
anol, and acetone [13, 5, 155].
Fluometuron is produced by reaction of 3-
trifluoromethylphenyl isocyanate with dimethy-
lamine [156].
Fluometuron is a selective, systemic, soil-
applied herbicide used to control annual broad-
leaved weeds and grasses in cotton and soya
beans. It inhibits photosynthesis.
Formulation. Suspension concentrate, wetta-
ble powder, dry flowable.
Trade Names. Cotogard, Cotoran, Meturon,
Cottonex, Fluometron.
Flometuron decomposes in soil and water-
sediment with half-lives of 85 and 524 d, respec-
234 Weed Control, 2. Individual Herbicides
tively. It is stable towards photolytic and hydro-
lytic action.
Isoproturon [34123-59-6], 3-(4-isopropyl-
phenyl)-1,1-dimethylurea, C12H18N2O, Mr
206.28, mp 158
C, log Kow 2.5, r 1.17 g/mL,
vapor pressure 5.5 mPa, consists of colorless
crystals which are slightly soluble in water,
heptane and hexane, moderately soluble in ben-
zene and xylene, and soluble in methanol, di-
chloromethane, and acetone [1, 2, 157].
Isoproturon is produced by reaction of 4-iso-
propylphenyl isocyanate with dimethylamine
[158].
Isoproturon is a selective, systemic herbicide,
absorbed by roots and foliage, used post-emer-
gence for the control of annual grasses and many
annual broad-leaved weeds in spring and winter
wheat, spring and winter barley, winter rye, and
titricale. It inhibits photosynthesis.
Formulation. Suspension concentrate.
Trade Names. Panron, Alon, Arelon, Strong,
Pasport, Trump, Ingot Javelin Gold.
Isoproturon decays with half-lives of 12, 48,
1560 and 149 d in soil, photolytically, hydrolyti-
cally, and in water-sediment, respectively.
Isouron [55861-78-4], 3-(5-tert-butylisoxa-
zol-3-yl)-1,1-dimethylurea, C10H17N3O2, Mr
211.36, mp 119120
C, consists of colorless crys-
tals which are sparingly soluble in water,and readi-
ly soluble in ethanol, acetone, and xylene [1, 2].
Isouron is produced by reaction of 3-tert-
butyl-isoxazol-2-yl isocyanate with dimethyla-
mine [159].
Isouron is a selective, systemic herbicide used
pre- and post-emergence for the control of broad-
leaved weeds and grasses in sugar cane and
pineapples.
Formulation. Wettable powder.
Trade Name. Isoxyl.
Vol. 39
Isouron decays in soil with a half-life of one
month.
Linuron [330-55-2], 3-(3,4-dichlorophe-
nyl)-1-methoxy-1-methylurea, C9H10Cl2N2O2,
Mr 249.09, mp 9395
C, log Kow 3.2, r
1.49 g/mL, vapor pressure 5.1 mPa, forms col-
orless crystals which are sparingly soluble in
water and aromatic and aliphatic hydrocarbons,
and readily soluble in acetone, ethanol, chloro-
form, and dimethylformamide [13, 160, 161].
Linuron is produced by reaction of 3,4-di-
chlorophenyl isocyanate with methoxymethyla-
mine [162].
Linuron is a selective, systemic herbicide with
contact and residual activities used pre- and post-
emergence to control annual grasses and broad-
leaved weeds, and some seedlings of perennial
weeds in a wide range of crops. It inhibits
photosynthesis.
Formulation. Suspension concentrate, water-
dispersible granules, wettable powder, emulsifi-
able concentrate.
Trade Names. Lorox, Afalon, Linex, Siolcid,
Bios, Uranus.
Linuron decomposes with half-lives of 48,
1460, and 46 d in soil, hydrolytically, and in
water-sediment, respectively. It is stable towards
photolytic action.
Methabenzthiazuron [1891-97-9], 1-(1,3-
benzothiazol-2-yl)-1,3-dimethylurea,
C10H11N3OS, Mr 221.27, mp 119121
C, log
Kow 2.64, r 1.33 g/mL, vapor pressure 5.9 mPa,
consists of colorless crystals which are sparingly
soluble in water, fairly soluble in methanol,
isopropyl alcohol, and toluene, and readily solu-
ble in acetone, dimethylformamide, and dichlor-
omethane [1, 2].
Methabenzthiazuron is produced by reaction
of 2-methylaminobenzothiazole with methyl iso-
cyanate [163].
Vol. 39
Methabenzthiazuron is a selective herbicide,
absorbed by roots and leaves, used to control a
broad spectrum of broad-leaved weeds and
grasses in cereals, legumes, maize, garlic, and
onions.
Formulation. Wettable powder.
Trade Name. Tribunil.
Methabenzthiazuron decays with half-lives of
135, 365 and 182 d in soil, hydrolytically, and in
water-sediment, respectively.
Metobenzuron [111578-32-6], ()-1-meth-
oxy-3-[4-(2-methoxy-2,4,4-trimethylchroman-7-
yloxy)phenyl]-1-methylurea, C22H28N2O5, Mr
40.5, mp 101.0102.5
C, is a colorless powder
which is sparingly soluble in water [1].
Metobenzuron is produced by reaction of 2-
(2-methoxy-2,4,4-trimethylchroman-7-yloxy)
phenyl isocyanate with dimethylamine [164].
Metobenzuron is a selective herbicide used
post-emergence to control a wide range of broad-
leaved weeds in maize.
Formulation. Wettable powder.
Trade Name. UMP-488.
Metobromuron [3060-89-7], 3-(4-bromo-
phenyl)-1-methoxy-1-methylurea, C9H11BrN2O2,
Mr 259.10, mp 95.596
C, log Kow 2.41, r 1.6 g/
mL, vapor pressure 0.4 mPa, consists of colorless
crystals which are sparingly soluble in water, fairly
soluble in hexane, and readily soluble in acetone,
dichloromethane, methanol, toluene, octanol, and
chloroform [13].
Metobromuron is produced by bromination of
3-phenyl-1-methoxy-1-methylurea [165].
Metobromuron is a selective, systemic herbi-
cide used pre-emergence for the control of annual
broad-leaved weeds and grasses in beans, pota-
toes, tomatoes, tobacco, soya beans, maize, ar-
tichokes, and sugar beet. It is also applied to the
soil surface. It inhibits photosynthesis.
Weed Control, 2. Individual Herbicides 235
Formulation. Wettable powder.
Trade Names. Patoran, Paltonex, Igrator,
Pattonex.
Metobromuron decays with half-lives of 30,
170, and 64 d in soil, hydrolytically, and in
water-sediment, respectively. It is stable towards
photolytic action.
Metoxuron [19937-59-8], 3-(3-chloro-4-
methoxyphenyl)-1,1-dimethylurea, C10H13ClN2O2,
Mr 228.68, mp 126127
C, log Kow 1.6, r 0.8 g/
mL, vapor pressure 4.3 mPa, forms colorless crys-
tals which are moderately soluble in water, diethyl
ether, benzene, and toluene, are practically insoluble
in petroleum ether, and are readily soluble in ace-
tone, cyclohexanone, acetonitrile, and hot ethanol
[1, 2].
Metoxuron is produced by reaction of 3-
chloro-4-methoxyphenyl isocyanate with di-
methylamine [147].
Metoxuron is a selective herbicide with resid-
ual activity used pre- and post-emergence for the
control of some grasses and annual broad-leaved
weeds in winter wheat, winter barley, winter rye,
and some varieties of spring wheat. It inhibits
photosynthesis.
Formulation. Wettable powder, soluble con-
centrate, wettable granules.
Trade Names. Dasonex, Deftor, Sulerex.
Metoxuron decomposes with half-lives of
18.5, 12, 24 and 145 d in soil, photolytically,
hydrolyticaly, and in sediment-water, respec-
tively.
Monolinuron [1746-81-2], 3-(4-chlorophe-
nyl)-1-methoxy-1-methylurea, C9H11ClN2O2,
Mr 214.65, mp 8083
C, log Kow 2.2, r 1.5 g/
mL, vapor pressure 0.0064 mPa, consists of
colorless crystals which are slightly soluble in
water, moderately soluble in hexane, and readi-
ly soluble in acetone, methanol, and toluene
[13].
236 Weed Control, 2. Individual Herbicides
Monolinuron is produced by reaction of 4-
chlorophenyl isocyanate with N-methylhydrox-
ylamine, followed by treatment with dimethyl
sulfate [166].
Monolinuron is a selective, systemic herbi-
cide, absorbed by roots and leaves and translo-
cated, used pre- and post-emergence to control
broad-leaved weeds and some annual grasses in
vegetables, ornamental shrubs, and trees. It in-
hibits photosynthesis.
Formulation. Wettable powder, emulsifiable
concentrate, colloidal suspension.
Trade Names. Arresin, Aresin, Afesin,
Monorotox, Premalin.
Monolinuron decomposes with half-lives of
60 and 22 d in soil and water-sediment, respec-
tively. It is stable against photolytic and hydro-
lytic actions.
Monuron [150-68-5], 3-(4-chlorophenyl)-
1,1-dimethylurea, C9H11ClN2O, Mr 198.65, mp
170.5171.5
C, log Kow 1.79, r 1.27 g/mL,
vapor pressure 0.067 mPa, is a colorless solid
with a slight odor which is sparingly soluble in
water, moderately soluble in methanol, ethanol,
and benzene, and soluble in acetone [2, 3, 5].
Monuron can be synthesized by reaction of
chlorophenyl isocyanate with dimethylamine [3].
Monuron is a broad-spectrum herbicide used
to control a wide range of annual and perennial
broad-leaved weeds and grasses on fruits and
vegetables. It inhibits photosynthesis.
Formulation. Wettable powder, granules,
oil-miscible liquids.
Trade Names. CMU Weedkiller, Amitrole,
Rosuran, Chlorea.
Monuron decays with a half-life of 170 d in
soil.
Neburon [555-37-3], 1-butyl-3-(3,4-di-
chlorophenyl)-1-methylurea, C12H16Cl2N2O, Mr
275.17, mp 102103
C, log Kow 3.8, r 1.25 g/
mL, vapor pressure 1.33 mPa, forms colorless
crystals which are practically insoluble in water,
and sparingly soluble in hydrocarbons [1, 2].
Vol. 39
Neburon is produced by reaction of 3,4-di-
chlorophenyl isocyanate with N-methylbutyla-
mine [154].
Neburon is a selective herbicide, absorbed by
roots, used pre-emergence for the control of
broad-leaved weeds and grasses in beans, peas,
cereals, beet, ornamentals, and in forestry. It is a
photosynthesis inhibitor.
Formulation. Wettable powder.
Trade Names. Granurex, Neburex, Kloben.
Neburon decays in soil with a half-life of
120 d. It is stable towards hydrolysis.
Siduron [1982-49-6], 1-(2-methylcyclo-
hexyl)-3-phenylurea, C14H20N2O, Mr 232.32, mp
133138
C, log Kow 2.7, r 1.08 g/mL, vapor
pressure 0.5 mPa, consists of colorless crystals
which are sparingly soluble in water, readily
soluble in dimethylformamide, ethanol, and di-
chloromethane [13, 167, 168].
Siduron is produced by reaction of phenyl
isocyanate with 2-methylcyclohexylamine
[169].
Siduron is a selective herbicide, absorbed by
roots and translocated, used pre-emergence to
control Digitaria sp. and annual grass weeds in
newly seeded grass or established turf.
Formulation. Pellets, granules, wettable
powder.
Trade Names. Tupersan, Weed Killer.
Siduron decomposes with half-lives of 135
and 290 d in soil and photolytically, respectively.
It is stable towards hydrolysis.
Tebuthiuron [34014-18-1], 1-(5-tert-
butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea,
C9H16N4OS, Mr 228.31, mp 162.9
C, log Kow
1.79, r 1.19 g/mL, vapor pressure 0.27 mPa,
forms off-white to buff crystals with a faint musty
odor which are moderately soluble in water,
benzene, and hexane, and readily soluble in
acetonitrile, acetone, methanol, and chloroform
[13, 5, 170].
Vol. 39
Tebuthiuron is produced by reaction of 5-tert-
butyl-2-N-methyl isocyanate-1,3,4-thiadiazole
with methylamine [171].
Tebuthiuron is a systemic broad-spectrum soil
herbicide with low selectivity, absorbed by roots
and translocated, used for the control of herba-
ceous and woody plants, as well as broad-leaved
weeds. It is also used for the control of total
vegetation in noncrop areas, undesirable plants in
pasture and rangeland, and broad-leaved weeds
and grass in sugar cane. It is a photosynthesis
inhibitor.
Formulation. Wettable powder, dry flow-
able, pellets.
Trade Names. Spike, Bushwacker, Tebusan,
EL-103.
Tebuthiuron decays with half-lives of 400 and
64 d in soil and hydrolytically, respectively.
Thidiazuron [51707-55-2], 1-phenyl-3-
(1,2,3-thiadiazol-5-yl)urea, C9H8N4OS, Mr
220.25, mp 211.5
C, log Kow 1.77, r 1.51 g/
mL, pKa 8.86, vapor pressure 3.0 nPa, forms
colorless crystals which are sparingly soluble in
water, hexane, and dichloromethane, slightly
soluble in toluene, moderately soluble in metha-
nol, and soluble in dimethylformamide and di-
methyl sulfoxide [1, 2, 172].
Thidiazuron can be synthesized by reaction of
5-(1,2,3-thiadiazole) isocyanate with aniline in
the presence of a base [54].
Thidiazuron is used as an herbicide and defo-
liant, absorbed by roots, used particularly in
cotton crops. It is a growth regulator.
Formulation. Emulsifiable concentrate, wet-
table powder.
Trade Names. Dropp, Abridor, Takedown,
FreeFall.
Thidiazuron decays in soil with a half-life of
85 d.
1.6. 2,6-Dinitroanilines
Benfluralin [1861-40-1], N-butyl-N-ethyl-
a,a,a-trifluoro-2,6-dinitro-p-toluidine,
C13H16F3N3O4, Mr 335.28, mp 65-66
C, bp
148149
C (931 Pa), log Kow 5.19, r 1.42 g/
mL, pKa 0.59, vapor pressure 1.73 mPa, forms
Weed Control, 2. Individual Herbicides 237
yellow-orange to colorless crystals which are
practically insoluble in water, fairly soluble in
hexane and methanol, and readily soluble in
acetone, ethyl acetate, dichloromethane, chloro-
form, toluene, and acetonitrile [13, 173, 174].
Benfluralin is produced by nitration of 4-
chloro-trifluorotoluene, followed by treatment
with N-ethylbutylamine [175].
Benfluralin is a selective soil herbicide that is
incorporated pre-emergence in the soil to control
annual grasses and some annual broad-leaved
weeds in peanuts, lettuce, cucumbers, chicory,
endive, field beans, French beans, etc. It inhibits
the assembly of microtubules.
Formulation. Emulsifiable concentrate, dry
flowable.
Trade Names. Balan, Team, XL-2G, Bene-
fex, Boanlan.
Benfluralin decays with half-lives of 40, 0.1
and 1.2 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards hy-
drolytic action.
Butralin [33629-47-9], (RS)-N-sec-butyl-
4-tert-butyl-2,6-dinitroaniline, C14H21N3O4, Mr
295.33, mp 6061
C, bp 134136
C (66.5 Pa),
log Kow 4.93, r 1.06 g/mL, vapor pressure 0.77 m
Pa, forms yellow-orange crystals with a slightly
aromatic odor which are sparingly soluble in
water, moderately soluble in methanol, and read-
ily soluble in n-heptane, xylene, and acetone
[13].
Butralin is produced by nitration of tert-butyl-
4-chlorobenzene and subsequent reaction with
sec-butylamine [176].
Butralin is a selective herbicide, absorbed by
germinating seedlings, used pre-emergence for
the control of annual broad-leaved weeds and
grasses in cotton, soya beans, rice, barley, beans,
vines, ornamentals, orchards of fruit and nut
trees, etc.
238 Weed Control, 2. Individual Herbicides
Formulation. Emulsifiable concentrate.
Trade Names. Amexine, Tamex, Tobago,
Amex, Zitsaosol.
Butralin decomposes with half-lives of 22 and
6.2 d in soil and water-sediment, respectively. It
is stable towards hydrolytic action.
Dinitramine [29091-05-2], N,N-diethyl-
2,6-dinitro-4-trifluoromethyl-m-phenylenedia-
mine, C11H13F3N4O4, Mr 322.24, mp 9899
C,
log Kow 4.3, r 1.47 g/ml, vapor pressure
0.479 mPa, consists of yellow crystals which are
sparingly soluble in water, moderately soluble in
n-hexane, and readily soluble in acetone, chloro-
form, benzene, xylene, and ethanol [13].
Dinitramine is produced by reaction of 2-
amino-3,5-dinitro-4-chlorotrifluorotoluene with
diethylamine [177].
Dinitramine is a selective soil herbicide, ab-
sorbed by roots and shoots, used pre-planting and
soil-incorporated for the control of many grass-
and broad-leaved weeds in cotton, vegetables,
sunflowers, transplanted tomatoes, aubergines,
etc. It prevents germination of seeds, and inhibits
root growth.
Formulation. Emulsifiable concentrate.
Trade Names Cobex, Cobeko, Diehtamine,
Cobexo.
Dinitramine decays with half-lives of 38 d
and 22 hours in soil and photolytically,
respectively.
Ethalfluralin [55283-68-6], N-ethyl-
a,a,a-trifluoro-N-(2-methylallyl)-2,6-dinitro-p-
toluidine, C13H14F3N3O4, Mr 333.30, mp 55
56
C, log Kow, vapor pressure 12 mPa, forms
yellow-orange crystals which are sparingly solu-
ble in water, and fairly soluble in acetone, aceto-
nitrile, benzene, chloroform, dichloromethane,
xylene, and methanol [13, 178].
Vol. 39
Ethalfluralin is produced by reaction of 2,6-
dinitro-4-trifluoromethylchlorobenzene with N-
ethylmethylallylamine [179].
Ethalfluralin is a selective soil herbicide used
pre-planting and soil-incorporated for the control
of most germinating annual grasses and broad-
leaved weeds in cotton, soya beans, dry beans,
lentils, peanuts, etc. It is a microtubule inhibitor.
Formulation. Emulsifiable concentrate, dry
flowable.
Trade Names. Sonalan, Edge, Gilan, Curbit.
Ethalfluralin decays with half-lives of 45, 0.3
and 13.5 d in soil, photolytically, and in water-
sediment. It is stable towards hydrolytic action.
Fluchloralin [33245-39-5], N-(2-chlor-
oethyl)-2,6-dinitro-N-propyl-4-trifluoromethy-
laniline, C12H13ClF3N3O4, Mr 355.70, mp 42
43
C, log Kow 5.07, vapor pressure 4.0 mPa, is a
yellow-orange solid with a faint medicinal odor
which is sparingly soluble in water, and readily
soluble in acetone, benzene, chloroform, diethyl
ether, ethyl acetate, cyclohexane, and ethanol
[13].
Fluchloralin is produced by reaction of 2,6-
dinitro-4-trifluoromethylchlorobenzene with N-
chloroethylpropylamine [180].
Fluchloralin is a selective herbicide used pre-
and post-emergence and soil-incorporated for the
control of annual grasses and some broad-leaved
weeds in several crops. It inhibits cell division.
Formulation. Emulsifiable concentrate.
Trade Names. Baselin, Technical, BAS-
392-H.
Fluchloralin decays with half-lives of 76 and
0.02 d in soil and photolytically, respectively. It
is stable towards hydrolytic action.
Isopropalin [33820-53-0], 4-isopropyl-
2,6,-dinitro-N,N-dipropylaniline, C15H23N3O4,
Mr 309.36, bp 40
C, log Kow 4.88, r 1.16 g/mL,
vapor pressure 3.6 mPa, is a red-orange liquid
which is practically insoluble in water, and solu-
ble in acetone, hexane, benzene, chloroform,
acetonitrile, and methanol [2, 3].
Vol. 39
Isopropalin can be prepared by reaction of
dipropylamine with 1-chloro-4-isopropyl-2,6-di-
nitrobenzene [3].
Isopropalin is a selective pre-emergence her-
bicide, soil incorporated, used to control grasses
and broadleaf weeds in transplanted tobacco. It is
an inhibitor of microtubular assembly.
Formulation. Emulsifiable concentrate.
Trade Names. Paarlan, EL-179.
Isopropalin decays in soil with a half-life of
100 d.
Nitralin [4726-14-1], 4-mesyl-2,6-dinitro-
N,N-dipropylaniline, C13H19N3O6S, Mr 345.37,
mp 151152
C, log Kow 2.92, vapor pressure
1.24 mPa, is a yellow solid with a mild chemical
odor which is practically insoluble in water,
poorly soluble in common hydrocarbon and aro-
matic solvents, and soluble in acetone, dimethyl-
sulfoxide [2, 3].
Nitralin can be made by reaction of dipropy-
lamine with 4-chloro-3,5-dinitrophenylmethyl
sulfone [3].
Nitralin is a selective pre-emergence herbi-
cide used to control many annual grasses in
beans, colza, and sunflowers.
Formulation. Wettable powder.
Trade Names. Planavalin, Planuin.
Nitralin decays with half-lives of 81 d and
2.43.7 months in soil and by biodegradation,
respectively.
Oryzalin [19044-88-3], 3,5-dinitro-N4,N4-
dipropylsulfanilamide, C12H18N4O6S, Mr
346.36, mp 137139
C, log Kow 3.73, pKa
9.4, vapor pressure 0.11 nPa, forms yellow-
orange crystals which are sparingly soluble in
water and n-heptane, moderately soluble in ben-
zene and xylene, and readily soluble in acetone,
acetonitrile, methanol, and dichloromethane,
[13, 5, 181].
Weed Control, 2. Individual Herbicides 239
Oryzalin is produced by reaction of 4-dipro-
pylamino-3,5-dinitrobenzenesulfonyl chloride
with ammonium hydroxide [182].
Oryzalin is a selective herbicide used pre-
emergence, surface-applied, for the control of
many annual grasses and broad-leaved weeds in a
variety of crops and in noncrop areas. It is a cell
division inhibitor.
Formulation. Wettable powder, suspension
concentrate, water-dispersible granules.
Trade Names. Surflan, Ryzelan, Dirimol,
Rout.
Oryzalin decays with half-lives of 20, 0.08,
and 33 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards hy-
drolytic action.
Pendimethalin [40487-42-1], N-(1-ethyl-
propyl)-2,6-dinitro-3,4-xylidine, C13H19N3O4,
Mr 281.31, mp 5658
C, bp 330
C, log Kow
5.2, r 0.85 g/mL, consists of yellow-orange
crystals which are sparingly soluble in water,
moderately soluble in n-hexane and n-octanol,
and soluble in xylene and acetone [13, 183,
184].
Pendimethalin is produced by reaction of 2,6-
dichloro-4,5-dimethyl chlorobenzene with 1-
ethylpropylamine [185]
Pendimethalin is a selective herbicide, ab-
sorbed by roots and leaves, used pre-planting
incorporated, and pre- and post-emergence for
the control of most annual grasses and many
broad-leaved weeds in a number of crops. It
inhibits cell division.
Formulation. Emulsifiable concentrate.
Trade Names. Herbadox, Prowl, Stomp,
Blazer, Bunker, Trump, Claymore.
Pendimethalin decays with half-lives of 90, 21
and 16 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards hy-
drolytic action.
240 Weed Control, 2. Individual Herbicides
Prodiamine [29091-21-2], 5-dipropylami-
no-a,a,a-trifluoro-4,6-dinitro-o-toluidine,
C13H17F3N4O4, Mr 350.29, mp 122.5124
C,
log Kow 4.10 d 1.41 g/mL, pKa 11.5, vapor pres-
sure 0.0033 mPa, forms yellow granules which
are practically insoluble in water, fairly soluble
in acetonitrile, benzene, ethanol, hexane, xylene,
and ethanol, and readily soluble in acetone and
chloroform [1, 2].
Prodiamine is produced by reaction of 2-ami-
no-3,5-dinitro-4-chloro-a,a,a-trifluorotoluene
with dipropylamine [186].
Prodiamine is a selective herbicide used pre-
planting or pre-emergence for the control of
annual grasses and broad-leaved weeds in cotton,
nonbearing fruit trees, vines, nuts, ornamentals,
turf, etc. It is cell division inhibitor.
Formulation. Water-dispersible granules,
wettable powder.
Trade Names. Barricade, Kusablock, Endur-
ance, Cavalcade.
Prodiamine decays in soil with a half-life of
120 d.
Profluralin [26399-36-0], N-cyclopropyl-
methyl-a,a,a-trifluoro-2,6-dinitro-N-propyl-p-
toluidine, C14H16F3N3O4, Mr 347,30, mp 32.1
32.5
C, log Kow 5.58, r 1.38 g/mL, vapor pres-
sure 8.4 mPa, forms yellow-orange crystals
which are practically insoluble in water, and
soluble in acetone, xylene, and ethanol [3].
Profluralin can be prepared by reaction of 4-
chloro-3,5-dinitrobenzotrifluoride with N-cylo-
propylmethyl-N,N-propylamine [3].
Profluralin is a pre- and post-emergence her-
bicide used on broadleaf weeds in soybeans,
peanuts, fruits and nut crops. It is more effective
on grasses than weeds.
Formulation. Emulsifiable concentrate.
Vol. 39
Trade Names. Tolban, B 4576.
Profluralin biodegrades with a half-life of
110 d.
Trifluralin [1582-09-8], a,a,a-trifluoro-2,6-
dinitro-N,N-dipropyl-p-toluidine, C13H16F3N3O4,
Mr 335.28, mp 4749
C, log Kow 5.25, r
1.36 g/mL, vapor pressure 9.5 mPa, forms
yellow-orange crystals which are sparingly
soluble in water, fairly soluble in methanol and
hexane, and readily soluble in acetone, chloroform,
acetonitrile, toluene, and ethyl acetate [13, 5, 187,
188].
Trifluralin is produced by nitration of 4-
chloro-trifluorotoluene, followed by treatment
with dipropylamine [189].
Trifluralin is a selective soil herbicide used
pre-emergence for the control of annual grasses
and broad-leaved weeds in many crops. It inhibits
cell division.
Formulation. Emulsifiable concentrate,
granules.
Trade Names. Treflan, Commerce. Zeltox-
one, Tri-4, Trifsan, Trilin, Triplen, Uranus,
Ardent.
Trifluralin decomposes with half-lives of 181,
0.4, and 5.5 d in soil, photolytically, and in
water-sediment, respectively. It is stable towards
hydrolytic action.
1.7. Imidazolinones
Imazamethabenz-methyl [81405-85-8],
consists of a mixture of methyl-6-[(RS)-4-isopro-
pyl-4-methyl-5-oxo-2-imidazolin-2-yl]-m-tolu-
ate and methyl-2-[(RS)4-isopropyl-4-methyl-5-
oxo-2-imidazolin-2-yl]-p-toluate, C16H20N2O3,
Mr 288.3, mp 113145
C, log Kow 1.54, r
0.3 g/mL, pKa 2.9, vapor pressure 1.5mPa, is a
fine to lumpy off-white powder with a slight
musty odor which is moderately soluble in
water, n-hexane, and n-heptane, and readily
soluble in chloroform, acetone, dimethyl sulf-
oxide, isopropyl alcohol, methanol, and toluene
[13, 190].
Vol. 39
Imazamethabenz-methyl is produced by reac-
tion of 3,4-(4,5)-dicarboxymethyltoluene with 2-
aminoamide-3-methylbutane in the presence of
two equivalents of potassium tert-butoxide
[191].
Imazamethabenz-methyl is a selective, sys-
temic herbicide which is effective post-emer-
gence against some broad-leaved and some di-
cotyledonous weeds in wheat, barley, rye, and
sunflowers.
Formulation. Suspension concentrate, emul-
sifiable concentrate, water-dispersible granules.
Trade Names. Assert, Dagger.
Imazamethabenz-methyl decays with half-
lives of 47, 36, and 133 d in soil, photolytically,
and hydrolytically, respectively.
Imazamox [114311-32-9], 2-[(R,S)-4-iso-
propyl-4-methyl-5-oxo-2-imidazolin-2-yl]-5-
methoxymethylnicotinic acid, C15H19N3O4, Mr
305.33, mp 166.0166.7
C, log Kow 5.36, r
1.39 g/mL,pKa 2.3, vapor pressure 0.0133 mPa,
forms colorless crystals which are practically
insoluble in hexane, sparingly soluble in toluene,
fairly soluble in acetone and ethyl acetone, and
soluble in methanol and water [13, 192].
Imazamox is produced by reaction of 2,3-
dicarboxymethyl-5-methoxymethylpyridine with
2-aminoamide-3-methylbutane in the presence of
two equivalents of potassium tert-butoxide [191].
Imazamox is a selective broad-spectrum her-
bicide with contact and residual activities, used
post-emergence for the control of broadleaf and
grass weeds in soya beans and other vegetables
grown in rotation with sugar beet and other crops.
It inhibits acetolactate synthase.
Formulation. Dry granules.
Trade Names. Odyssey, Sweeper, Raptor.
Weed Control, 2. Individual Herbicides 241
Imazamox decays with half-lives of 25, 0.3,
and 142 d in soil, photolytically, and in water-
sediment. It is stable towards hydrolytic action.
Imazapic [104098-48-8], 2-[(R,S)-4-iso-
propyl-4-methyl-5-oxo-2-imidazolin-2-yl]-5-
methylnicotinic acid, C14H17N3O3, Mr 275.30,
mp 204206
C, log Kow 2.47, r 1.31 g/mL, pKa
2.0, vapor pressure 0.01 mPa, is a pale tan to
colorless powder which is moderately soluble in
water and acetone [1, 2].
Imazapic is produced by reaction of 2,3-di-
carboxymethyl-5-methylpyridine with 2-ami-
noamide-3-methylbutane in the presence of two
equivalents of tert-butoxide [193].
Imazapic is a selective systemic herbicide
with contact and residual activities used early
post-emergence for the control of a wide range of
weeds in peanuts. It inhibits biosynthesis of
amino acids necessary for cell division and
growth.
Formulation. Soluble concentrate.
Trade Name. Cadre.
Imazapic decays with half-lives of 120 and
0.3 d in soil and photolytically, respectively.
Imazapyr [81334-34-1], 2-[(RS)-4-isopro-
pyl-4-methyl-5-oxo-2-imidazolin-2-yl]nicotinic
acid, C13H15N3O3, Mr 261.28, mp 169171
C,
log Kow 0.11, r 1.34 g/mL, pKa1 1.9, pKa2 3.6,
pKa3 11, vapor pressure 0.013 mPa, is an off-
white to tan powder with a slight ammoniacal
odor which is sparingly soluble in hexane, mod-
erately soluble in water, toluene, soluble in ace-
tone, methanol, dichloromethane, and dimethyl-
formamide [13, 194].
Imazapyr is produced by reaction of 2,3-di-
carboxymethylpyridine with 2-aminoamide-3-
242 Weed Control, 2. Individual Herbicides
methylbutane in the presence of two equivalents
of tert-butoxide [195].
Imazapyr is a nonselective, systemic herbi-
cide with residual activity, absorbed by foliage
and rapidly translocated, used pre- and post-
emergence for the control of annual and peren-
nial grasses, sedges, broad-leaved weeds, many
bushes, and deciduous tree species on noncrop
areas. It acts by interfering with an enzyme in the
biosynthetic pathway.
Formulation. Suspension concentrate, emul-
sifiable concentrate.
Trade Name. Arsenal.
Imazapyr decomposes with half-lives of 11,
2.1, and 30 d in soil, photolytically, and hydro-
lytically, respectively.
Imazaquin [81335-37-7], 2-[(R,S)-4-iso-
propyl-4-methyl-5-oxo-2-imidazolin-2-yl]quin-
oline-2-carboxylic acid, C17H17N3O3, Mr
311.33, mp 219224
C, log Kow 1.09, r
0.41 g/mL, pKa1 3.45, pKa2 11.03, vapor pressure
0.7 fPa, is a gray crystalline solid which is
sparingly soluble in toluene, moderately soluble
in acetone, and ethyl acetate, fairly soluble in
dimethylformamide, dimethyl sulfoxide, and
dichloromethane, and soluble in water [13,
196].
Imazaquin is produced by reaction of 2,3-
dicarboxymethylquiniline with 2-aminoamide-
3-methylbutane in the presence of two equiva-
lents of tert-butoxide [195].
Imazaquin is a selective, systemic herbicide,
absorbed by roots and foliage, used pre-planting,
pre-emergence, and early post-emergence to
control broad-leaved weeds in soya beans. It is
an acetolactate synthase inhibitor.
Formulation. Suspension concentrate, liquid
concentrate.
Trade Names. Scepter, Meteor, Upright.
Imazaquin decays with half-lives of 60, 0.75,
and 516 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards hy-
drolytic action.
Vol. 39
Imazethapyr [81335-77-5], 5-ethyl-2-
[(RS)-4-isopropyl-4-methyl-5-oxo-2-imidazo-
lin-2-yl]nicotinic acid, C15H19N3O3, Mr 289.33,
mp 171173
C, log Kow 1.49, r 1.11g/mL, pKa1
2.1, pKa2 3.9, vapor pressure 0.0133 mPa, forms
colorless crystals which are moderately soluble
in water, toluene, and heptane, and readily solu-
ble in acetone, methanol, dichloromethane, and
dimethyl sulfoxide [13].
Imazethapyr is produced by reaction of 2,3-
dicarboxymethyl-5-ethylpyridine with 2-ami-
noamide-3-methylbutane in the presence of two
equivalents of tert-butoxide [195].
Imazethapyr is a systemic herbicide with con-
tact and residual activities, used pre-plant-incor-
porated, pre- and post-emergence for the control
of many annual and perennial grasses and broad-
leaved weeds in soya beans and other leguminous
crops. It is an acetolactate synthase inhibitor.
Formulation. Aqueous solution.
Trade Names. Hammer, Overtop, Pivot,
Pursuit.
Imazethapyr decays with half-lives of 90 and
52 d in soil and photolytically, respectively. It is
stable towards hydrolytic action.
1.8. Phenoxy Compounds
Bromofenoxim [13181-17-4], 3,5-dibro-
mo-4-hydroxybenzaldehyde 2,4-dinitropheny-
loxime, C13H7Br2N3O6, Mr 461.05, mp 196
197
C, log Kow 3.3, r 2.135 g/mL, pKa 5.46,
vapor pressure 1.16 nPa, forms cream-colored
crystals which are sparingly soluble in water,
moderately soluble in hexane, isopropyl alcohol,
and n-octanol, and fairly soluble in acetone [1, 2].
Bromofenoxim is produced by reaction of 3,5-
dibromoanisaldehyde oxime with 2,4-dinitro-
Vol. 39
chlorobenzene in the presence of sodium ethox-
ide [197].
Bromofenoxim, a precursor of bromoxynil, is
a selective contact herbicide used post-emer-
gence by foliar application to control many an-
nual broad-leaved weeds in cereals, maize, grass-
seed crops, on grassland, and newly seeded turf.
It inhibits photosystem II.
Formulation. Suspension concentrate, wetta-
ble powder.
Trade Names. Faneron, Bromfenin.
Bromofenoxim decays with half-lives of 53,
25 and 7 d in soil, hydrolytically (produces bro-
moxynil, see below) and in water-sediment,
respectively.
Clodinafop-propargyl [105512-06-9],
prop-2-ynyl (R)-2-[4-(5-chloro-3-fluoro-2-pyri-
dyloxy)phenoxy]propanoate, C17H13ClFNO4,
Mr 349.8, mp 59.5
C, bp 100.6
C, log Kow
3.90, r 1.35 g/mL, vapor pressure 3.19 mPa, is
a creamy to colorless crystalline powder which is
practically insoluble in water, moderately solu-
ble in n-hexane, fairly soluble in ethanol and n-
octanol, and soluble in acetone, toluene, and
ethyl acetate [13, 198, 199].
Clodinafop-propargyl can be made by reac-
tion of 2-fluoro-4-chloropyridine with propynyl
2-(4-chlorophenoxy)propionate [3].
Clodinafop-propargyl is a systemic herbicide
with contact activity used to control weeds and
grasses in spring wheat. It inhibits the biosynthe-
sis of lipids.
Formulation. Emulsion concentrate, tech-
nical.
Trade Names. Topik, Discover, Celio.
Clodinafop-propargyl decays with half-lives
of 0.8, 24, 4.8, and 0.2 d in soil, photolytically,
hydrolytically, and in water-sediment, respec-
tively.
Clomeprop [84496-56-0], (R,S)-2-(2,4-di-
chloro-m-tolyloxy)propionanilide, C16H15Cl2NO2,
Mr 324.20, mp 146147
C, bp 302.5308.5
C,
log Kow 4.80, r 1.391 g/mL, vapor pressure
<0.013 mPa, consists of colorless crystals which
are practically soluble in water, fairly soluble in
Weed Control, 2. Individual Herbicides 243
xylene, acetone, cyclohexane, and dimethylforma-
mide [1, 200].
Clomeprop is produced by reaction of the
potassium salt of 2,4-dichloro-3-methylphenol
with 2-chloropropionanilide [201].
Clomeprop is a selective, auxin-type herbi-
cide used pre- to early post-emergence to control
broad-leaved weeds and cyperaceous weeds in
paddy rice. It inhibits protein biosynthesis.
Formulation. Granules.
Trade Names. Yukahope, Cente.
Clomeprop decays with half-lives of 331 h
and 1 year photolytically and hydrolytically,
respectively.
Cloprop [101-10-0], (RS)-2-(3-chlorophe-
noxy)propionic acid, C9H9ClO3, Mr 200.62, mp
113
C, bp 100
C (200 Pa), log Kow 2.39, pKa
3.62, vapor pressure 0.03 mPa, is a colorless
crystalline solid which is slightly soluble in
water, moderately soluble in benzene, and solu-
ble in acetone, methanol, ethanol, dimethylfor-
mamide [13].
Cloprop can be synthesized by reaction of 2-
chlorophenol with 2-chloropropionic acid in the
presence of base [3].
Cloprop is a plant growth regulator used as
fruit thinner, size increaser for pineapple, as a
defoliant, and to control broadleaf plants and
brushes.
Formulation. Wettable powder, suspension
concentrate.
Trade Names. Amchem, Bidisin, Fruitone.
Cloprop decays in air with a half-life of 16 h.
Cyhalofop-butyl [122008-85-9], butyl (R)-
2-[4-(4-cyano-2-fluorophenoxy)phenoxy]pro-
panoate, C20H20FNO4, Mr 357.4, mp 45.5
49.5
C, bp >270
C (decomp.), log Kow 3.31,
r 1.172 g/ml, vapor pressure 0.053 mPa, is a
colorless crystalline solid which is practically
insoluble in water, moderately soluble in heptane
244 Weed Control, 2. Individual Herbicides
and n-octanol, and soluble in acetone, dichlor-
omethane, methanol, acetonitrile, and ethyl ace-
tate [2, 3, 202, 203].
Cyhalofop-butyl is made by reaction of 2-
chloro-4-cyanophenol with butyl 2-(4-chloro-
phenoxy)propionate [3].
Cyhalofop-butyl is a systemic, post-emer-
gence herbicide, absorbed by foliage, used to
control grass weeds in rice. It possesses no soil
activity.
Formulation. Emulsion concentrate, gran-
ules, oil emulsion in water.
Trade Names. Cleaner, Clincher, Agrostar,
Clincher Bas.
Cyhalofop-butyl decays with half-lives of 0.2,
27, 97, and 0.13 d in soil, photolytically, hydro-
lytically, and in water-sediment, respectively.
2,4-D [94-75-7], (2,4-dichlorophenoxy)
acetic acid, C8H6Cl2O3, Mr 221.04, mp 139
140.5
C, bp 160
C (53 Pa), log Kow 0.83, r
1.57 g/mL, pKa 2.87, vapor pressure 0.0187 mPa,
forms colorless crystals with a slight phenolic
odor which are moderately soluble in water,
heptane, toluene, dichloromethane, and xylene,
and readily soluble in ethanol, acetone, methanol,
and diethyl ether [13, 5, 204207].
2,4-D is produced by interaction of 2,4-di-
chlorophenolate with monochloroacetic acid
[208].
2,4-D is a selective, systemic herbicide, ab-
sorbed by roots, it acts as a growth inhibitor, and
is used post-emergence for the control of annual
and perennial weeds in many crops. It is a
synthetic auxin; it damages vascular tissues.
Formulation. Suspension concentrate, emul-
sifiable concentrate, water-dispersible granules,
granules.
Trade Names. Ded-Weed, Desormone,
U46D, Weedtox, Depitox, Esteem, Polo.
2,4-D decays with half-lives of 10, 13, and
29 d in soil, photolytically, and in water-sedi-
Vol. 39
ment, respectively. It is stable towards hydrolytic
action.
2,4-DB [94-82-6], 4-(2,4-dichlorophenoxy)
butyric acid, C10H10Cl2O3, Mr 249.09, mp 115
118
C, bp 324.35
C, log Kow 1.35, r 1.46 g/
mL, pKa 4.1, vapor pressure 9.44 mPa, consists of
colorless crystals with a slight phenolic odor
which are moderately soluble in water, readily
soluble in acetone, ethanol, ethyl acetate, and
diethyl ether, and slightly soluble in benzene and
toluene [13, 5, 209211].
2,4-DB is produced by reaction of 2,4-dichlor-
ophenol with trimethylene chlorobromide, fol-
lowed by reaction with sodium cyanide and
hydrolysis of the resulting cyano compound to
the acid [212].
2,4-DB is a selective, systemic, hormone-type
herbicide used post-emergence for the control of
many annual and perennial broad-leaved weeds
in alfalfa, clovers, under-sown cereals, grassland,
etc. It causes stem and leaf malformations.
Formulation. Suspension concentrate, emul-
sifiable concentrate.
Trade Names. Embutox, Butormone, Butox-
one, Butyrac, Embutone.
2,4-DB decays with half-lives of 16, 17.2, and
17 d in soil, photolytically, and in water-sedi-
ment, respectively. It is stable towards hydrolytic
action.
Dichlorprop [7547-66-2], (R,S)-2-(2,4-di-
chlorophenoxy)propionic acid, C9H8Cl2O3, Mr
235.06, mp 116117.5
C, log Kow 2.29, r
1.42 g/mL, pKa 3, vapor pressure 0.01 mPa, forms
colorless crystals which are moderately soluble in
water,and readily soluble in acetone, isopropyl
alcohol, benzene, toluene, and xylene [13, 213].
Dichlorprop is produced by reaction of 2-
chloropropionic acid with 2,4-dichlorophenol
[214].
Vol. 39
Dichlorprop is a selective, systemic, hor-
mone-type herbicide used post-emergence to
control annual and perennial broad-leaved weeds
in cereals and grassland, as well as for brush
control on noncropland.
Formulation. Suspension concentrate, emul-
sifiable concentrate, granules.
Trade Names. Weedone, U46 DPC, Poly-
mone, Diprop, Desormone.
Dichlorprop decays with a half-life of 10 d in
soil. It is stable towards hydrolytic action.
Dichlorprop-P [15165-67-0], (R)-2-(2,4-
dichlorophenoxy)propionic acid, C9H8Cl2O3, Mr
235.06, mp 121123
C, log Kow 0.56, r
1.42 g/ml, pKa 3.67, vapor pressure 0.056 mPa,
forms colorless crystals which are moderately
soluble in water, readily soluble in acetone and
ethanol, ethyl acetate, and fairly soluble in tolu-
ene [13, 215217].
Dichlorprop-P is produced analogously to
dichlorprop, but from the ()-stereoisomer
of propionic acid, obtained by fermentation
[218].
Dichlorprop-P is a selective, systemic, hor-
mone-type herbicide used post-emergence for
the control of various weed species.
Formulation. Suspension concentrate.
Trade Names. Link, Optica.
Dichlorprop-P decomposes with half-lives of
14, 4, and 15 d in soil, photolytically, and in
water-sediment, respectively.
Diclofop-methyl [51338-27-3], methyl (R,
S)-2-[4-(2,4-dichlorophenoxy)phenoxy]propano-
ate, C16H14Cl2O4, Mr 341.19, mp 3941
C, log
Kow 4.6, r 1.3 g/mL, vapor pressure 0.25 mPa,
forms colorless crystals which are sparingly sol-
uble in water, and readily soluble in acetone, ethyl
acetate, and toluene [13, 5, 219].
Weed Control, 2. Individual Herbicides 245
Diclofop-methyl is produced by reaction of
2,4-dichlorophenol with methyl 4-bromophe-
noxy-2-propionate [220].
Diclofop-methyl, a fatty acid synthesis inhib-
itor, is a selective, systemic herbicide used post-
emergence to control wild oats, wild millet, and
other annual grass weeds in many crops.
Formulation. Emulsifiable concentrate, oil in
water emulsion.
Trade Names. Hoegrass, Hoelon, Illoxan,
Tigres Uktra, Keylofop.
Disul-sodium [136-78-7], 2-(2,4-dichloro-
phenoxy)ethyl hydrogen sulfate, C8H7Cl2NaO5S,
Mr 309.09, mp 245
C (decomp.), r 1.70 g/mL,
vapor pressure 133 Pa, is a colorless crystalline
solid which is insoluble in most organic solvents,
except methanol,and soluble in water [3].
Disul-sodium can be prepared by reaction of
oxirane with 2,4-dichlorophenol and treating the
resulting alcohol with chlorosulfonic acid and
sodium sulfate [3].
Disul-sodium is used pre-emergence to con-
trol annual weeds in maize, sweetcorn, gladioli,
narcissi, vegetables, and fruits.
Formulation. Water-soluble powder.
Trade Names. Sesone, Crag Herbon.
Disul-sodium decays in soil with a half-life of
0.51.5 months.
Fenoxaprop-ethyl [66441-23-4], ethyl
(RS)-2-[4-(6-chloro,1,3-benzoxazol-2-yloxy)phe-
noxy]propanoate, C18H16ClNO5, Mr 361.78, mp
8485
C, bp 200
C (100 Pa), log Kow 4.28, r
1.3 g/mL, vapor pressure 1.9 mPa, is a colorless
solid which is sparingly soluble in water, n-hexane,
and cyclohexane, and soluble in ethyl acetate,
toluene, and acetone [13].
246 Weed Control, 2. Individual Herbicides
Fenoxaprop-ethyl can be made by reaction of
6-chlorobenzoxazole with ethyl 4-chlorophe-
noxy-2-propionate [3].
Fenoxaprop-ethyl is a selective, post-emer-
gence herbicide used to control grassy weeds in
broadleaved crops and established turf grass, and
annual and perennial grass weeds in beans, beets,
cotton, nuts, potatoes, soybeans, vegetables. It
inhibits the biosynthesis of fatty acids.
Formulation. Emulsifiable concentrate.
Trade Names. Acclaim, Depon, Excel, Fu-
rore, Option, Puma.
Fenoxaprop-ethyl decays with half-lives of 5,
171, 100, and 1 d in soil, photolytically, hydro-
lytically, and in water-sediment respectively.
Fenoxaprop-P-ethyl [71283-80-2], ethyl
(R)-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy)
phenoxy]propanoate, C18H16ClNO5, Mr 361.78,
mp 86.5
C, log Kow 4.58, r 1.32 g/mL, vapor
pressure 0.53 mPa, is a colorless solid which is
sparingly soluble in water, moderately soluble
in n-hexane, and soluble in acetone, methanol,
and ethyl acetate [1, 2, 221, 222].
For synthesis, see parent compound fenoxa-
prop-ethyl.
Fenoxaprop-P-ethyl is a selective, systemic
herbicide with contact activity used to control
annual and perennial grass weeds and wild oats in
wheat, rye, triticate. It inhibits fatty acid
biosynthesis.
Formulation. Emulsion oil in water, emulsi-
fiable concentrate.
Trade Names. Cheetah Super, Foxtrot, Ti-
gress Ultra, Triumph, Puma S.
Fenoxaprop-P-ethyl decays with half-lives of
0.4, 105, 23, and 0.1 d in soil, photolytically,
hydrolytically, and in water-sediment,
respectively.
Fluazifop-butyl [69806-50-4], butyl (RS)-
2-{4-[5-(trifluoromethyl)-2-pyridyloxy]phe-
noxy}propanoate, C19H20F3NO4, Mr 383.36, mp
13
C, bp 165
C (2.6 Pa), log Kow 4.5, r 1.21 g/
mL, vapor pressure 0.056 mPa, is a pale straw-
colored liquid which is practically insoluble in
water, and miscible with acetone, xylene, meth-
Vol. 39
anol, cyclohexanone, and dichloromethane
[13].
Fluazifop-butyl can be prepared by reaction of
n-butanol with 2-(4-chlorophenoxy)propionic
acid, followed by treatment of the thus-obtained
product with 2-hydroxy-5-(trifluoromethyl)pyri-
dine [112].
Fluazifop-butyl is a selective, systemic herbi-
cide, absorbed by leaves, used post-emergence to
control annual and perennial grasses and weeds.
In plants it is rapidly hydrolyzed to the parent
compound fluazifop [69335-91-7]. It interferes
with ATP production in plants.
Formulation. Emulsifiable concentrate, wet-
table powder.
Trade Names. Onecide, Supelco, Halokan.
Fluazifop-butyl decays with a half-life of 21 d
in soil.
Fluazifop-P-butyl [79241-46-6], butyl (R)-
2-{4-[5-trifluoromethyl)-2-pyridyloxy]phenoxy}
propanoate, C19H20F3NO4, Mr 383.36, mp 46
C, log Kow 4.5, r 1.22 g/mL, vapor pressure
0.12 mPa, is a straw-colored liquid which is spar-
ingly soluble in water, and miscible with xylene,
acetone, methanol, and toluene [1, 2, 5, 223].
For synthesis, see parent compound Fluazi-
fop-butyl.
Fluazifop-P-butyl is a selective herbicide,
absorbed by leaves, used to control annual and
perennial weeds and grasses.
Formulation. Emulsifiable concentrate.
Trade Names. Fusilade, Max, Greencrop
Bantry.
Vol. 39
Fluazifop-P-butyl decays with half-lives of
28, 6, 78, and 1.6 d in soil, photolytically, hy-
drolytically, and in water-sediment, respectively.
Haloxyfop [69806-34-4], (RS)-2-{4-[3-
chloro-5-(trifluoromethyl)-2-pyridyloxy]phe-
noxy}propionic acid, C15H11ClF3NO4, Mr
361.72, mp 107108
C, d 1.64, pKa 2.9, vapor
pressure 1.33 mPa, is a colorless crystalline prod-
uct which is sparingly soluble in water, slightly
soluble in hexane, and soluble in acetone, ethyl
acetate, and xylene [1, 2, 5].
Haloxyfop can be prepared by reaction of 2,3-
dichloro-5-(trifluoromethyl)pyridine with 2-(4-
hydroxyphenoxy)propionic acid in the presence
of a base [112].
Haloxyfop is a selective herbicide, absorbed
by roots and foliage, used to control broad-leaved
weeds and grasses in a number of crops. It is
usually used as an ester (e.g., haloxyfop-ethtyl
[87237-48-7], haloxyfop-methyl [69806-40-2]).
It inhibits fatty acid biosynthesis.
Formulation. Emulsion concentrate.
Trade Names. Verdict, Gallant, Zellek.
Haloxyfop decays with half-lives of 9, 12, and
40 d in soil, photolytically, and in water-sedi-
ment, respectively.
Haloxyfop-P [95977-29-0], (R)-2-{4-[3-
chloro-5-(trifluoromethyl)-2-pyridyloxy]phe-
noxy}propionic acid, C15H11ClF3NO4, Mr
361.72, mp 72.5
C, log Kow 0.27, r 1.46 g/mL,
pKa 4.27, vapor pressure 4.0 mPa, is an off-white
powder which is moderately soluble in n-hep-
tane, and soluble in water, acetone, and methanol
[1, 2, 224, 225].
For synthesis, see parent compound
Haloxafop.
Weed Control, 2. Individual Herbicides 247
Haloxyfop-P is a selective herbicide, ab-
sorbed by roots and foliage, used to control
broad-leaved weeds and grasses in grapes.
Formulation. Emulsifiable concentrate.
Trade Names. Edge, DE-535.
Haloxyfop-P decays with half-lives of 0.5, 12,
and 0.1 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards hy-
drolytic action.
MCPA [94-74-6], 4-chloro-o-tolyloxyace-
tic acid, C9H9ClO3, Mr 200.62, mp 119
120.5
C, log Kow 3.25, r 1.41, pKa 3.73, vapor
pressure 0.4 mPa, consists of colorless crystals
which are sparingly soluble in hexane, moder-
ately soluble in water, fairly soluble in toluene,
xylene, and heptane, and readily soluble in etha-
nol and diethyl ether [13, 226, 227].
MCPA is produced by chlorination of o-
cresol and coupling with monochloroacetic acid
[228].
MCPA is a selective, systemic, hormonelike
herbicide used post-emergence for the control of
annual and perennial broad-leaved weeds in cer-
eals, vegetables, grassland turf, roadside verges,
embankments, forestry, etc.
Formulation. Suspension concentrate, emul-
sifiable concentrate, water soluble powder.
Trade Names. Agrotone, Meadowman, Em-
pel, Sanphen-M, Cedar, Agrotox.
MCPA decays with half-lives of 15, 0.05, and
17 d in soil, photolytically, and in water-sedi-
ment. It is stable towards hydrolytic action.
MCPA-thioethyl [25319-90-8], S-ethyl 4-
chloro-o-tolyloxythioacetate, C11H13ClO2S, Mr
244.74, mp 4142
C, log Kow 4.45, r 1.291 g/
mL, vapor pressure 0.13 mPa, forms colorless
needles which are sparingly soluble in water, and
readily soluble in acetone, xylene, hexane, and
ethyl acetate [1, 2].
248 Weed Control, 2. Individual Herbicides
MCPA-thioethyl is produced by reaction of
ethyl mercaptan with 4-chloro-2-methylphenox-
ymethylcarboxychloride [229].
MCPA-thioethyl is a selective, systemic, hor-
monelike herbicide, translocated, used post-
emergence to control annual and perennial
broad-leaved and cyperaceous weeds in orch-
ards, paddy rice, and cereals.
Formulation. Suspension concentrate.
Trade Names. Fenobit, Herbit, Zero One.
MCPA-thioethyl is degraded photolytically
with a half-life of 1 d.
MCPB [94-81-5], 4-(4-chloro-o-tolyloxy)
butyric acid, C11H13ClO3, Mr 228.67, mp 98
100
C, bp > 280
C, log Kow 1.32, r 1.233 g/
mL, pKa 4.5, vapor pressure 0.004 mPa, consists
of colorless crystals which are sparingly soluble
in hexane, moderately soluble in water, fairly
soluble in toluene, and readily soluble in acetone,
dichloromethane, and ethanol [13, 230, 231].
MCPB is produced by chlorination of o-cresol
and coupling with g-chlorobutyric acid [232].
MCPB is used as a sodium salt [6062-26-6],
and is a selective, systemic, hormone-type her-
bicide, translocated, used post-emergence for the
control of annual and perennial broad-leaved
weeds in cereals, clovers, peas, peanuts, grass-
lands, and forestry.
Formulation. Suspension concentrate,
technical.
Trade Names. Tropotox, Butoxone, Tropo-
tox Plus.
MCPB decays with half-lives of 7, 2.6, and
17 d in soil, photolytically, and in water-sedi-
ment, respectively. It is stable towards hydrolytic
action.
Mecoprop [7085-19-0], (RS)-2-(4-chloro-
o-tolyloxy)propionic acid, C10H11ClO3, Mr
214.65, mp 9495
C, log Kow 3.13, r 1.37 g/
ml, pKa 3.2, vapor pressure 0.31 mPa, forms
colorless crystals which are moderately soluble
in heptane, and soluble in water, acetone, diethyl
ether, ethanol, ethyl acetate, and chloroform
[13, 5, 233].
Vol. 39
Mecoprop is produced by chlorination of 4-
chloro-o-cresol and coupling with 2-chloropro-
pionic acid [232].
Mecoprop is a selective, systemic, hormone-
like herbicide used post-emergence for the con-
trol of broad-leaved weeds in wheat, barley, oats,
seed crops, grassland, under fruit trees, etc.
Formulation. Suspension concentrate, emul-
sifiable concentrate, granules, powder.
Trade Names. Actril, Propal, Propionyl,
Compitox, Mecopex, Mecoper.
Mecoprop decays with half-lives of 8.2 and
4 d in soil and photolytically, respectively. It is
stable towards hydrolytic action.
Mecoprop-P [16484-77-8], (R)-2-(4-
chloro-o-tolyloxy)propionic acid, C10H11ClO3,
Mr 214.65, mp 94.696.2
C, log Kow 0.02, r
1.31 g/mL, pKa 3.86, vapor pressure 0.23 mPa, is
a colorless to tan crystalline solid which is spar-
ingly soluble in water, and soluble acetone,
diethyl ether, ethanol, dichloromethane, metha-
nol, ethyl acetate, and toluene [1, 2, 235, 236].
Mecoprop-P is produced analogously to Me-
coprop from the corresponding propionic acid
stereoisomer [237].
Mecoprop-P is a selective, systemic, hor-
monelike herbicide, absorbed by leaves and
translocated to roots, used post-emergence for
the control of broad-leaved weeds in wheat,
barley, oats, seed crops, grassland, etc.
Formulation. Suspension concentrate.
Trade Names. Duplosan KV, Optica, Com-
petox Plus, Foundation, Prompt.
Mecoprop-P decays with half-lives of 8, 44
and 50 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards hy-
drolytic action.
Metamifop [256412-89-2], (R)-2-[4-(6-
chloro-1,3-benzoxazol-2-yloxy)phenoxy]-2 0 -
Vol. 39
fluoro-N-methylpropionanilide, C23H18ClFN2O4,
Mr 440.86, mp 77.5
C, log Kow 5.47, r 1.39 g/
mL, vapor pressure 0.151 mPa, is a beige powder
which is sparingly soluble in water, moderately
soluble in n-heptane, and soluble in acetone, meth-
anol, xylene, ethyl acetate, and dichloromethane [2,
238].
Metamifop can be prepared by reaction of 2,6-
dichloro-1,3-benzoxazole with 4-hydroxyphe-
noxy-N-(2-fluorophenyl)-N-methylpropanamide
[238].
Metamifop is a selective herbicide used to
control a wide range of annual grass weeds in
cereal crops and rice. It is a fatty acid biosynthe-
sis inhibitor.
Formulation. Granules, emulsifiable
concentrate.
Trade Name. DBH-129.
Metamifop decays with a half-life of 70 d in
soil.
Propaquizafop [111479-05-1], 2-isopropy-
lideneaminooxyethyl (R)-2[4-(6-chloroquinoxa-
lin-2-yloxy)phenoxy]propionate, C22H22ClN3O5,
Mr 443.88, mp 66.3
C, log Kow 4.78, r 0.96 g/
mL, vapor pressure 0.44 nPa, forms colorless
crystals which are sparingly soluble in water,
readily soluble in acetone and toluene, and
fairly soluble in n-hexane and ethanol [1, 2,
239].
Propaquizafop is produced by reaction of 2-
(6-chloroaminoxalinyl)phenoxypropionic acid
ethoxycarbonyl chloride with isopropylidene hy-
droxylamine [240].
Propaquizafop, which inhibits fatty acid syn-
thesis, is a systemic, post-emergence herbicide,
absorbed by roots and foliage and translocated,
used for the control of a wide range of annual and
perennial grasses in soya beans, sugar cane,
cotton, vegetables, etc.
Weed Control, 2. Individual Herbicides 249
Formulation. Emulsifiable concentrate.
Trade Names. Agil, Falcon, Zealot, Shogun.
Propaquizafop decays with half-lives of 2.1,
32, 32, and 33 d in soil, photolytically, hydrolyt-
ically, and in water-sediment, respectively.
Quizalofop-ethyl [76578-14-8], ethyl (RS)-
2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]pro-
panoate, C19H17ClN2O4, Mr 372.8, mp 91.7
92.1
C, bp 220
C (26.6 Pa), log Kow 4.28, r
1.35 g/mL, vapor pressure 0.86 mPa, is a color-
less crystalline material which is practically in-
soluble in water, moderately soluble in ethanol
and hexane, and soluble in benzene, xylene,
acetone, and methanol [13].
Quizalofop-ethyl can be prepared by reaction
of 4-chloro-o-phenylenediamine with glyoxylic
acid, followed by reaction of the intermediate
product with 2-(4-chlorophenoxy)propionic acid
in ethanol [3].
Quizalofop-ethyl is a systemic, selective her-
bicide, absorbed by leaves and translocated,
used post-emergence to control annual and pe-
rennial grass weeds in potatoes, soybeans, sugar
beet, peanuts, oilseed rape, sunflowers, vegeta-
ble, cotton, etc. It is a fatty acid biosynthesis
inhibitor.
Formulation. Emulsifiable concentrate, sus-
pension concentrate.
Trade Names. Targa, Assure, Pilot, DPY-
Y6202.
Quizalofop-ethyl decomposes with half-lives
of 45, 0.01, and 2 d in soil, photolytically, and
hydrolytically, respectively.
Quizalofop-P-ethyl [100646-51-3], ethyl
(R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]
propionate, C19H17ClN2O4, Mr 372.81, mp
75
C, log Kow 4.61, r 1.36 g/mL, vapor pressure
0.11 mPa, is a colorless crystalline solid which is
sparingly soluble in water, and moderately solu-
ble in methanol, and soluble in acetone, ethyl
acetate, and xylene [1, 2, 5, 241, 242].
250 Weed Control, 2. Individual Herbicides
For synthesis, see Quizalofop-ethyl.
Quizalofop-P-ethyl is a selective herbicide
used post-emergence to control annual and pe-
rennial grass weeds in a range of crops. It inhibits
the biosynthesis of fatty acids.
Formulation. Emulsion concentrate, suspen-
sion concentrate.
Trade Names. Leopard, Pilot Ultra.
Quizalofop-P-ethyl decays with half-lives of
2, 38, 112, and 1.5 d in soil, photolytically,
hydrolytically, and in water-sediment,
respectively.
2,4,5-T [93-76-5], (2,4,5-trichlorophenoxy)
acetic acid, C8H5Cl3O3, Mr 255.49, mp 153
C,
log Kow 4, pKa 2.88, vapor pressure 0.01 mPa, is a
light tan to colorless solid which is very slightly
soluble in petroleum ether, slightly soluble in
xylene, toluene, and n-heptane, and moderately
soluble in ethanol, isopropyl alcohol, and diethyl
ether [13, 243].
2,4,5-T can be made by reaction of 2,3,5-
trichlrophenol with monochloroacetic acid in the
presence of a base [3].
2,4,5-T is a post-emergence herbicide used
alone or in combination with 2,4-D to control
shrubs and trees, and is also used for girding,
injection, or cut-stump treatment.
Formulation. Emulsifiable concentrate, sus-
pension concentrate.
Trade Names. 2,4,5-T, Silvex.
2,4,5-T decays with half-lives of 441 and
15 d in soil and photolytically, respectively. It is
stable towards hydrolytic action.
1.9. Triazoles
Amicarbazone [129909-90-6], 4-amino-N-
tert-butyl-4,5-dihydro-3-isopropyl-5-oxo-1H-
1,2,4-triazole-1-carboxamide, C10H19N5O2, Mr
241.9, mp 137.5
C, log Kow 1.23, r 1.12 g/mL,
vapor pressure 0.0013 mPa, is a colorless crys-
talline product which is sparingly soluble in n-
heptane, moderately soluble in water and xylene,
and soluble in ethyl acetate, acetonitrile, acetone,
dimethyl sulfoxide, and dichloromethane [2, 3,
Vol. 39
244].
Amicarbazone can be synthesized by reaction
of 4-amino-4,5-dihydro-3-(1-methylethyl)-5-
oxo-1H-1,2,4-triazole with tert-butylcarbamoyl
chloride in the presence of a base [245].
Amicarbazone is a selective herbicide with
contact activity, absorbed by foliage, used pre-
plant, pre-emergence, early post-emergence
through ground application to control annual
weeds and grasses in sugar cane, corn, and other
crops. It is a photosystem II inhibitor.
Formulation. Water-dispersible granules,
dustable powder.
Trade Names. Dinomic, Technical.
Amicarbazone decays with half-lives of 21,
60, and 64 d in soil, photolytically, and hydro-
lytically, respectively.
Amitrole [61-82-5], 1H-1,2,4-triazol-3-yla-
mine, C2H4N4, Mr 84.08, mp 157159
C, log
Kow 0.97, r 1.14 g/ml, pKa1 4.14, pKa2 10.7,
vapor pressure 0.033 mPa, consists of colorless
crystals with a bitter taste which are readily
soluble in water, moderately soluble in methanol,
acetonitrile, and chloroform, sparingly soluble in
ethyl acetate, and practically insoluble in ethyl
acetate, diethyl ether, acetone, and nonpolar
solvents [13, 246248].
Amitrole is produced by condensation of for-
mic acid with aminoguanidine [249].
Amitrole is a nonselective herbicide, foliar-
acting and translocated, which inhibits the bio-
synthesis of chlorophyll and regrowth from buds.
It is used for the total control of annual and
perennial grasses and broad-leaved weeds
around established fruit trees and bushes in orch-
ards, in vineyards, and in many other appli-
cations.
Formulation. Suspension concentrate, water-
soluble powder, flakes, soluble concentrate.
Vol. 39
Trade Names. Weedazal, Superzol, Oriflam,
Amizine, Kleer-lot.
Amitrole decomposes with half-lives of 18
and 31 d in soil and water-sediment, respective-
ly. It is stable towards photolytic and hydrolytic
action.
Azafenidin [68049-83-2], 2-(2,4-dichloro-5-
prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-
triazolo[4,3-a]pyridin-3(2H)-one, C15H13Cl2N3O2,
Mr 338.19, mp 168168.5
C, log Kow 2.71, r
1.4 g/mL, vapor pressure 1.0 nPa, forms a rust-
colored solid which is sparingly soluble in water
[1, 2].
Azafenidin is produced by reaction of N-(2-
piperidyl)-N0 -(2,4-dichloro-5-oxy-methylacety-
lene)hydrazone with methyl chloroformate
[250].
Azafenidin is a selective herbicide with some
residual activity used pre-emergence to control
broad-leaved weeds and grasses in citrus, grapes,
sugar cane, and other perennial crops.. It is an
inhibitor of the biosynthesis of porphyrin.
Formulation. Suspension concentrate, wetta-
ble powder.
Trade Name. Milestone.
Azafenidin decays with half-lives of 67 and
6.5 d in soil and photolytically, respectively. It is
stable toward hydrolytic action.
Bencarbazone [173980-17-1], 4-[4,5-dihy-
dro-4-methyl-5-oxo-3-(trifluoromethyl)-1H-1,2,4-
triazol-1-yl]-2-[(ethylsulfonyl)amino]-5-fluoro-
benzenecarbothioamide, C13H13F4N5O3S2, Mr
427.40 [251].
Bencarbazone is a new, selective herbicide
intended for use on weeds and grasses in various
crops.
Weed Control, 2. Individual Herbicides 251
Formulation. Granules, emulsifiable con-
centrate.
Trade Name. Midas.
Cafenstrole [125306-83-4], N,N-diethyl-3-
mesitylsulfonyl-1H-1,2,4-triazole-1-carboxamide,
C16H22N4O3S, Mr 350.44, mp 114116
C, log
Kow 3.21, r 1.30 g/mL, vapor pressure 53 nPa,
forms colorless crystals which are practically in-
soluble in water [1, 2].
Cafenstrole is produced by reaction of 2-sul-
fonyl-(20 ,40 ,60 -trimethylphenyl)-1,3,4-triazole
with N-diethylcarbamoyl chloride [252].
Cafenstrole is used pre- and early post-emer-
gence for the control of annual weeds in paddy
rice. It inhibits cell division.
Formulation. Suspension concentrate.
Trade Name. CH-900, Grachitor.
Cafenstrole decays in soil with a half-life of
8 d.
Carfentrazone-ethyl [128639-02-1], ethyl
(RS)-2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-
4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazoel-1-
yl]-4-fluorophenyl}propanoate, C15H13Cl2F3N3O3,
Mr 412.19, mp 22.1
C, bp 350355
C (101
kPa), log Kow 3.36, r 1.46 g/mL, vapor pressure
7.2 mPa, is a yellow viscous liquid which is spar-
ingly soluble in water and toluene, moderately
soluble in hexane, and soluble in acetone, ethanol,
ethyl acetate, and dichloromethane [2, 3, 253, 254].
Carfentrazone-ethyl can be made by reaction
of 4-(difluoromethyl)-4,5-dihydro-3-methyl-5-
oxo-1H-1,2,4-triazole with a,2,5-trichloro-4-
fluorobenzenepropanoic acid in the presence of
a base [255].
Carfentrazone-ethyl is a herbicide with con-
tact activity, absorbed by foliage, limited trans-
location, used post-emergence to control broad-
252 Weed Control, 2. Individual Herbicides
leaved weeds in wheat, corn, soy beans and also
as a defoliant in cotton. It acts by disruption of
cell membranes.
Formulation. Wettable powder, wettable-
dispersible granules.
Trade Names. Ally Express, Lexus, Class,
Aim, Shark, Aurora.
Carfentrazone-ethyl decays with half-lives of
0.5, 8.3, 13.7, and 0.4 d in soil, photolytically,
hydrolytically, and in water-sediment, res-
pectively.
Cloransulam-methyl [147150-35-4], (its
acid: [159518-97-5]), methyl 3-chloro-2-(5-eth-
oxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-
ylsulfonamido)benzoate, C15H13ClFN5O5S, Mr
429.81, mp 216218
C, log Kow 0.365, r
1.54 g/mL, pKa 4.81, vapor pressure 0.04 mPa,
is an off-white powder which is slightly soluble
in water, methanol, and ethyl acetate, and mod-
erately soluble in acetone and dichloromethane
[13, 256].
Cloransulam-methyl is produced by conden-
sation of 5-oxyethyl-7-fluoro-1,2,4-triazolo[1,5-
c]pyrimidine-2-sulfonyl chloride with 2-carbox-
ymethyl-6-chloroaniline [257].
Cloransulam-methyl is an acetolactate-
synthase inhibitor, used pre- and post-emergence
for the control of broad-leaved weeds in soya
beans and other crops. It is applied only on the
ground.
Formulation. Water-dispersible granules,
Trade Name. First Rate.
Cloransulam-methyl decays with half-lives of
11, 0.01, and 175 d in soil, photolytically, and
hydrolytically.
Diclosulam [145701-21-9], 20 ,60 -dichloro-
5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimi-
dine-2-sulfonanilide, C 13H 10 Cl 2FN 5O 3S, M r
406.22, mp 220
C,log Kow 0.85, r 1.74 g/mL,
pKa 4.0, vapor pressure 0.67 fPa, is an off-white
to brown granular solid which is sparingly solu-
ble in water, and moderately soluble in acetone,
dichloromethane, and ethyl acetate [2].
Vol. 39
Diclosulam can be made by reaction of 5-
ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimi-
dine-2-sulfonylchloride with 2,6-dichloroaniline
in the presence of a base [258].
Diclosulam is applied to the ground used to
control broad-leaved weeds in peanuts, soya
beans, sugar cane, and other crops. It inhibits
acetolactate synthase.
Formulation. Wettable granules, granules.
Trade Names. Strongarm, XDE-564.
Diclosulam decays in soil with a half-life of
49 d.
Florasulam [145701-23-1], 2 0 ,6 0 ,8-tri-
fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimi-
dine-2-sulfonanilide, C 12 H 8 F 3 N 5 O 3 S, M r
359.28, mp 193.7
C, log Kow 1.22, r 1.53 g/
mL, pKa 4.54, vapor pressure 0.01 mPa, is a
colorless solid which is sparingly soluble in
xylene, practically insoluble in n-heptane,
moderately soluble in methanol and water, and
soluble in acetone and acetonitrile [2,
259261].
Florasulam can be prepared by reaction of
5-methoxy-6-fluoro[1,2,4]triazolo[1,5-c]pyrim-
idine2-sulfonylchloride with 2,6-difluoroaniline
in the presence of a base [258].
Florasulam is applied post-emergence to con-
trol various broad-leaved weeds on cereal grains,
including wheat, barley, oats, rye, and triticate. It
inhibits acetolactate synthase.
Formulation. Wettable granules, suspension
concentrate.
Trade Names. Primus, Cabadex, Junction,
Barton, Boxer.
Florasulam decays with half-lives of 8.5, 156,
and 13 d in soil, photolytically, and in water-
sediment, respectively.
Vol. 39 Weed Control, 2. Individual Herbicides 253

Flucarbazone-sodium [181274-17-9], sodi- control broad-leaved weeds and some grasses on

um 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-
{[2-(trifluoromethoxy)phenyl]sulfonyl}-1H-1,2,4-
triazole-1-carboxamide, C12H10F3N4NaO6S, Mr
418.28, mp 200
C (decomp.), log Kow 1.84, r
1.59 g/mL, pKa 1.9, vapor pressure <1.0 nPa, is a
colorless crystalline solid which is moderately
soluble in water [2, 262].
corn and soybeans. The product SureStart is only
used on herbicide-tolerant field and silage corn. It
is an acetolactate synthase inhibitor.
Formulation. Water-dispersible granules,
emulsifiable concentrate, wettable powder.
Trade Names. Broadstrike, Preside, Python,
Scorpion, Hornet.
Flumetsulam decays with half-lives of 45 and
270 d in soil and photolytically, respectively.

Flupoxam [119126-15-7], 1-[4-chloro-3-

(2,2,3,3,3-pentafluoropropoxymethyl)phenyl-
5-phenyl-1H-1,2,4-triazole-3-carboxamide,
C19H14ClF5N4O2,Mr 460.79, mp 144146
C,
vapor pressure 0.02 mPa, forms light beige crys-
tals which are practically insoluble in water, and
Flucarbazone-sodium can be prepared by re- readily soluble in methanol, acetone, and ethyl
action of 4-methyl-4,5-dihydro-3-methoxy-5- acetate [1, 2].
oxotriazole with 2-(trifluoromethyl)phenyl sul-
famoyl chloride [258].
Flucarbazone-sodium, absorbed by roots and
foliage and translocated, is used post-emergence
to control grasses and some broad-leaved weeds
in cereals and wild oats, and to suppress yellow
foxtail and ryegrass. It inhibits acetolactate
synthase.
Flupoxam is produced by reduction of the
Formulation. Dry flowable, granules.
nitro group of 2-chloro-5-nitrobenzene, followed
Trade Name. Everest.
by diazotization, addition of benzylamino ethyl-
Flucarbazone-sodium decays in soil with a
carboxylate, and cyclization of the product [266].
half-life of 17 d. It is stable towards photolytic
Flupoxam is a cell-elongation inhibitor, used
and hydrolytic action.
pre- and post-emergence to control annual broad-
leaved weeds in winter wheat and winter barley.
Flumetsulam [98967-40-9], 20 ,60 -difluoro-
Formulation. Suspension concentrate.
5-methyl[1,2,4]triazolo[1,5,-a]pyrimidine-2-
Trade Names. Ovation, Quantum.
sulfonanilide, C12H9F2N5O2S, Mr 325.29, mp
250251
C, log Kow 0.21, r 1.77 g/mL, pKa
Ipfencarbazone [212201-70-2], 1-(2,4-di-
4.6, vapor pressure 0.37 fPa, is an off-white solid
chlorophenyl)-20 ,40 -difluoro-1,5-dihydro-N-iso-
which is insoluble in hexane and xylene, and
propyl-5-oxo-4H-1,2,4-triazole-4-carboxamide,
moderately soluble in water, acetone, and meth-
C18H14Cl2F2N4O2, Mr 427.23 [2].
anol [2, 263265].

Flumetsulam can be made by reaction of 5-

methyl[1,2,4]triazolo-2-sulfonylchloride with
2,6-difluoroaniline in the presence of a base
[258].
Flumetsulam is a selective, systemic herbi-
cide, absorbed by roots and leaves, used to
254 Weed Control, 2. Individual Herbicides
Ipfencarbazone is a new herbicide (Hokko
Chemicals Industry Co. Ltd.) of which no further
data are yet available.
Metosulam [139528-85-1], 20 ,60 -dichloro-
5,7-dimethoxy-30 -methyl[1,2,4]triazolo[1,5-a]
pyrimidine-2-sulfonanilide, C14H13Cl2N5O4S,
Mr 418.26, mp 210211.5
C, log Kow 2.46. d
1.49 g/mL, pKa 4.8, vapor pressure 0.4 fPa, is a
cream- to tan-colored powder which is sparingly
soluble in water and toluene, and moderately
soluble in acetone, acetonitrile, methanol, ethyl
acetate, and dichloromethane [1, 2].
Metosulam is produced by reaction of 4,6-
dimethoxy-(2-sulfonyl)-2,3-triazolyl pyrimi-
dine chloride with 2,6-dichloro-5-methylani-
line [267].
Metosulam, which inhibits acetolactate
synthase, is used pre- and post-emergence for
the control of broad-leaved weeds in wheat,
barley, rye, and maize.
Formulation. Suspension concentrate.
Trade Names. Pronto, Sansac, Sinal, Tacco.
Metosulam decays with half-lives of 19, 31,
and 8 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards hy-
drolytic action.
Penoxsulam [219714-96-2], 3-(2,2-di-
fluoromethoxy)-N-(5,8-dimethoxy[1,2,4]tria-
zolo[1,5-c]pyrimidine-2-yl)-a,a,a-trifluoroto-
luene-2-sulfonamide, C16H14F5N5O5S, Mr
483.37, mp 223224
C, log Kow 0.354, r
1.61 g/mL, pKa 5.1, vapor pressure 0.03 fPa, is
an off-white powder which is sparingly soluble
in water and octanol, moderately soluble in
methanol, and soluble in acetone and acetoni-
trile [2, 268, 269].
Vol. 39
Penoxsulam can be prepared by reaction of 2-
amino-5,8-dimethoxy-1,2,4-triazole with 2-(2,2-
difluoroethyl)-6-trifluoromethylbenzenesulfonyl
chloride in the presence of a base [258].
Penoxsulam is a new herbicide used post-
emergence to control annual and perennial
broad-leaved weeds, certain grasses, and aquatic
plants in rice. It is an inhibitor of acetolactate
synthase.
Formulation. Granules, suspension concen-
trate.
Trade Names. Galleon, Grasp, Saphire,
Granite, Viper.
Penoxsulam decays with half-lives of 32 and
2 d in soil and photolytically, respectively. It is
stable towards hydrolytic action.
Propoxycarbazone-sodium [181274-15-
7], sodium 4,5-dihydro-N-{[2-(methoxycarbonyl)
phenyl]sulfonyl}-4-methyl-5-oxo-3-propoxy-1H-
1,2,4-triazole-1-carboximidate, C15H17N4NaO7S,
Mr 420.37, mp 230240
C (decomp.), log Kow
1.55, r 1.42 g/mL, pKa 2.1, vapor pressure <10
nPa, is a crystalline solid which is sparingly soluble
in acetone, xylene, and n-heptane, moderately
soluble in dichloromethane, and soluble in water
[2, 270].
Propoxycarbazone-sodium can be synthe-
sized by reaction of 4-methyl-4,5-dihydro-3-pro-
poxy-5-oxo-1H-1,2,4-triazole-2-carbamate with
methyl 2-sulfonylchloride benzoate in the pres-
ence of a base [258].
Propoxycarbazone-sodium is a herbicide with
residual activity, absorbed by leaves and roots
and translocated, used to control various annual
and perennial grasses, and some broad-leaved
weeds, in rye, triticate, wheat. It is an acetolactate
synthase inhibitor.
Formulation. Water-dispersible granules,
water-soluble granules.
Trade Names. Attribut, Olympus.
Propoxycarbazone-sodium decomposes with
half-lives of 23, 18, and 101 d in soil, photolyti-
cally and in water-sediment, respectively. It is
stable towards hydrolytic action.
Vol. 39
Pyroxsulam [422556-08-9], N-(5,7-di-
methoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-
methoxy-4-(trifluoromethyl)pyridine-3-sulfon-
amide, C14H13F3N6O5S, Mr 434.35, mp 208
C,
log Kow 1.01, r 1.62 g/mL, pKa 4.67, vapor
pressure 0.1 mPa, is a colorless powder which is
slightly soluble in xylene and octanol, moderately
soluble in water, ethyl acetate, and dichloro-
methane, and soluble in methanol and acetone
[2, 271, 272].
Pyroxsulam can be synthesized by reaction of
5-methoxy-8-trifluoro-1,2,4-triazole-2-sulfonyl
chloride with 2,6-difluoroaniline in the presence
of a base [258].
Pyroxsulam is a new post-emergence herbi-
cide with a very broad spectrum, foliar and soil
activity, and translocation, used to control annual
grasses and broad-leaved weeds in winter wheat.
It inhibits acetolactate synthase.
Formulation. Water-dispersible granules,
suspension concentrate.
Trade Names. Admit, GF-1274.
Pyroxsulam decays with half-lives of 10 and
3.2 d in soil and photolytically, respectively. It is
stable towards hydrolytic action.
Sulfentrazone [122836-35-5], 20 ,40 -di-
0 herbicide, absorbed by roots and leaves, with
chloro-5 -(difluoromethyl-4,5-dihydro-3-meth-
yl-5-oxo-1,2,4-triazole-1-yl)methanesulfonani-
lide, C11H10Cl2F2N4O3S, Mr 387.19, mp 121
123
C, log Kow 1, r 0.53 g/mL, pKa 6.56, vapor
pressure 0.13 mPa, is a light brown solid with a
faint sulfur odor which is sparingly soluble in
water [2, 3, 273, 274].
Sulfentrazone can be prepared by reaction of
4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-
1H-1,2,4-triazole with 2,4,5-trichloromethane-
sulfonanlide in the presence of a base [258].
Weed Control, 2. Individual Herbicides 255
Sulfentrazone is used to control broad-leaved
weeds and some grasses especially in soya beans,
tobacco, and sugar cane, but also in turf grass and
railroad yards.
Formulation. Water-dispersible granules,
wettable powder, flowable liquid.
Trade Names. Authority, Gauntlet.
Sulfentrazone decays in soil with a half-life of
541 d. It is stable towards photolytic and hydro-
lytic action.
Thiencarbazone-methyl [317815-83-1],
methyl 4-[(4,5-dihydro-3-methoxy-4-methyl-5-
oxo-1H-1,2,4-triazole-1-yl)carbonylsulfamoyl]-5-
methylthiophene-3-carboxylate, C12H14N4O7S,
Mr 390.44, mp 205
C, log Kow 1.98, is a color-
less powder which is sparingly soluble in water [2,
275].
Thiencarbazone-methyl can be obtained by
reaction of 4-methyl-3-methoxy-5-oxo-1H-
1,2,4-triazole-2-amide with methyl 5-methyl-3-
thiophenecarboxylate-4-sulfonyl chloride in the
presence of a base [54].
Thiencarbazone-methyl is a new, systemic
contact and residual activity used to control
grasses on corn.
Formulation. Water-dispersible granules,
suspension concentrate.
Trade Name. Adengo.
Thiencarbazone-methyl decays with half-
lives of 17 and 90.6 d in soil and photolytically,
respectively.
1.10. Uracils
Benzfendizone [158755-95-4], methyl (RS)-
2-(5-ethyl-2-{4-[1,2,3,6-tetrahydro-3-methyl-2,6-
dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenox-
ymethyl}phenoxy)propionate, C25H25F3N2O6, Mr
506.47, log Kow 4.24, r 1.32 g/mL, is a colorless
solid which is sparingly soluble in water [2].
256 Weed Control, 2. Individual Herbicides
Benzfendizone can be prepared by reaction of
2-methylene chloride-5-phenoxymethylproprio-
nate with 4-chlorophenol followed by coupling
of the product to 1,2,3,6-terahydro-3-methyl-4-
(trifluoromethyl)-2,6-dioxoypyrimidine in the
presence of a base [276].
Benzfendizone is used post-emergence to
control grasses and broad-leaved weeds in
orchards and other no-till situations. It can also
be used as a potato desiccant and cotton defo-
liant. It is an inhibitor of protoporphyrinogen
oxidase.
Formulation. Microemulsion.
Trade Names. F3686, FMC-143686.
Bromacil [314-40-9], (RS)-5-bromo-3-sec-
butyl-6-methyluracil, C9H13BrN2O2, Mr 261.12,
mp 157.5160
C, log Kow 1.88, r 1.59 g/mL,
pKa 9.27, vapor pressure 15 nPa, consists of
colorless crystals which are slightly soluble in
water, and moderately soluble in xylene, acetone,
acetonitrile, ethanol [13, 277].
Bromacil is produced by reaction of isopropyl
isocyanate with methyl 3-aminocrotonate, fol-
lowed by cyclization in sodium hydroxide at
elevated temperature, and bromination in acetic
acid [278].
Bromacil is a nonselective herbicide, ab-
sorbed by roots, used for the total control of
weeds and brushes on noncropland, and also for
the selective control of annual and perennial
weeds and grasses in citrus and pineapple planta-
tions. It inhibits photosystem II.
Formulation. Granules, water-dispersible
granules, wettable powder, liquids.
Trade Names. Hyvar X, Rokar XL, Uragan,
Weed-Brom.
Bromacil decays in soil with a half-life of 60 d.
It is stable towards photolytic and hydrolytic
actions.
Vol. 39
Butafenacil [134605-64-4], 1-(allyloxycar-
bonyl)-1-methylethyl-2-chloro-5-[1,2,3,6-tetra-
hydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)
pyrimidin-1-yl]benzoate, C20H18ClF3N2O6, Mr
474.81, mp 113
C, bp 270
C, log Kow 3.2, r
1.37 g/mL, vapor pressure 7.4 nPa, is a colorless
powder which is sparingly soluble in water [2,
279].
Butafenacil can be made by reaction of 1-
(allylcarbonyl)-1-methylethyl 2,5-dichloroben-
zoatewith 1,2,3,6-tetrahydro-3methyl-2,6-di-
oxo-4-(trifluoromethyl)pyrimidine in the pres-
ence of a base [258].
Butafenacil is a nonselective herbicide with
contact activity, absorbed by foliage, used to
control annual and perennial broad-leaved weeds
in fruit crops, vineyards, noncropping land, and
as a defoliant in cotton. It inhibits protoporphyr-
inogen oxidase.
Formulation. Emulsifiable concentrate.
Trade Name. Rebin.
Butafenacil decays with half-lives of 1.5, 28,
98, and 27 d in soil, photolytically, hydrolytical-
ly, and in water-sediment, respectively.
Lenacil [2164-08-1], 3-cyclohexyl-1,5,6,7-
tetrahydrocyclopentapyrimidine-2,4-(3H)-
dione, C13H18N2O8, Mr 234.29, mp 315.6
316.8
C, log Kow 1.69, r 1.32 g/mL, pKa
10.7, vapor pressure 1.7 nPa, forms colorless to
tan colored crystals which are practically insolu-
ble in water and hexane, and slightly soluble in
acetone, toluene, and ethyl acetate [1, 2, 280,
281].
Lenacil is produced by condensation of cy-
clohexylurea and ethyl 2-oxocyclopentane-1-
carboxylate with phosphoric acid [282].
Lenacil is a selective, systemic herbicide with
residual activity, absorbed by roots, used for the
control of annual grasses and broad-leaved
Vol. 39
weeds in sugar cane, beet, fodder beet, sweet
potatoes, etc., and in ornamental plants and
shrubs. It inhibits photosystem II.
Formulation. Wettable powder, water-dis-
persible granules.
Trade Names. Venzar, Adol, Venus, Lence.
Lenacil decays with half-lives of 179 and
112 d in soil and in water-sediment, respectively.
It is stable towards photolytic and hydrolytic
actions.
Saflufenacil [372137-35-4], N0 -{2-chloro-
4-fluoro-5-[1,2,3,6-tetrahydro-3-methyl-2,6-di-
oxo-4-(trifluoromethyl)pyrimidin-1-yl]benzo-
yl}-N-isopropyl-N-methylsulfamide,
C17H17ClF4N4O5S, Mr 500.92 [2].
Saflufenacil can be produced by reaction of
1,2,3,6-tetrahydro-3-methyl-4-(trifluoromethyl)-
2,6-dioxopyrimidine with 2,5-dichloro-4-fluoro-
benzoyl-N-isopropyl-N-methylsulfamide in the
presence of a base [24].
Saflufenacil is a new herbicide with contact
and residual activities, used alone or in mixtures
with glyphosate for rapid control of many dicot-
yledonous weeds. It is also used pre-emergence
in corn and sorghum, and used to control various
weeds in citrus fruit trees, nut trees, pome fruit
trees, and stone fruit trees.
Formulation. Granules, water-dispersible
granules.
Trade Name. Kixor.
Terbacil [5902-51-2], 3-tert-butyl-5-
chloro-6-methyluracil, C9H13ClN2O2, Mr
216.67, mp 175177
C, log Kow 1.89, r
1.34 g/mL, pKa 9.5, vapor pressure 0.0625 mPa,
consists of colorless crystals which are sparingly
soluble in water, moderately soluble in dimethyl-
formamide, and soluble in cyclohexanone, meth-
yl isobutyl ketone, and butyl acetate [13, 5, 283].
Weed Control, 2. Individual Herbicides 257
Terbacil is produced by reaction of tert-butyl
isocyanate with methyl 3-aminocrotonate, fol-
lowed by cyclization and chlorination [112].
Terbacil is a selective herbicide, absorbed
mainly by roots, used for the control of many
annual and some perennial weeds in apples,
citrus, peaches, and other crops.
Formulation. Wettable powder.
Trade Names. Sinbar, Geonter.
Terbacil decays with a half-life of 115 d in
soil. It is stable towards hydrolytic action.
1.11. Pyridines
Aminopyralid [150114-71-9], 4-amino-
3,6-dichloropyridine-2-carboxylic acid,
C6H4Cl2N2O2, Mr 207.03, mp 162165
C, log
Kow 2.87, r 1.76 g/mL, pKa 2.6, vapor pressure
9.5 nPa, is an off-white powder which is practi-
cally insoluble in heptane, sparingly soluble in
xylene, moderately soluble in acetone and ethyl
acetate, and soluble in water and methanol [2,
284, 285].
Aminopyralid can be produced from a-pico-
line by chlorination, followed by hydrolysis of
the chlorinated product, and amination, in anal-
ogy to picloram [286].
Aminopyralid is a selective herbicide used
post-emergence for a long-term control of nox-
ious and invasive broad-leaved weeds in grass-
land, wheat, barley, corn, etc.
Formulation. Emulsifiable concentrate, sus-
pension concentrate.
Trade Names. Milestone, Simplex, Banish,
ForeFront.
Aminopyralid decays with half-lives of 32,
0.6, 0.6, and 712 d in soil, photolytically, hydro-
lytically, and in water-sediment, respectively.
Clopyralid [1702-17-6], 3,6-dichloropyri-
dine-2-carboxylic acid, C6H3Cl2NO2, Mr
192.0, mp 151152
C, log Kow 2.63, r
1.76 g/mL, pKa 2.01, vapor pressure 1.36 mPa,
forms colorless crystals which are moderately
258 Weed Control, 2. Individual Herbicides
soluble in xylene and n-hexane, fairly soluble in
water, acetonitrile, methanol, n-hexane, and eth-
yl acetate [13, 287].
Clopyralid is produced by photochlorination
of picoline, followed by further photochlorina-
tion and oxidation [288].
Clopyralid is a selective, systemic herbicide,
absorbed by leaves and roots, with auxin-type
activity, used post-emergence for the control of
many annual and perennial broad-leaved weeds
in sugar beet, fodder beet, oilseed rape, maize,
etc.
Formulation. Wettable powder, suspension
concentrate.
Trade Names. Cyranal, Clio,Benzalox, Cam-
paign, Cirtoxin.
Clopyralid decomposes with half-lives of 34
and 271 d in soil and photolytically, respectively.
It is stable towards hydrolytic action.
Diflufenican [83164-33-4], 20 ,40 -difluoro-
2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide,
C19H11F7N2O2, Mr 394.29, mp 159161
C,
log Kow 4.2, r 1.54 g/mL, vapor pressure
4.25 mPa, forms colorless crystals which are
practically insoluble in water, moderately sol-
uble in methanol, and soluble in ethyl acetate,
acetone, and dichloromethane [1, 2, 289, 290].
Diflufenican is produced by reaction of 2-(3-
trifluoromethylphenoxy)nicotinic acid with 2,4-
difluoroaniline and sulfonyl chloride [291].
Diflufenican is an inhibitor of carotenoid and
photosynthesis electron flow. It is a selective
contact and residual herbicide used pre- and early
post-emergence to control grass and broad-
leaved weeds in autumn-sown wheat and barley.
Formulation. Suspension concentrate.
Trade Names. Fenican, Javelin, Absolute,
Ardent, Bacara, Regatta.
Vol. 39
Diflufenican decays with half-lives of 542,
123, and 175 d in soil, photolytically, and in
water-sediment, respectively. It is stable towards
hydrolytic action.
Diflufenzopyr [109293-97-2], 2-{(EZ)1-[4-
(3,5-difluorophenyl)semicarbazono]ethyl}nico-
tinic acid, C15H12F2N4O3, Mr 334.28, mp
155
C, log Kow 1.09, r 0.24 g/mL, pKa 3.18,
vapor pressure 0.01 mPa, is an off-white to col-
orless solid which is moderately soluble in water
[13].
Diflufenzopyr is produced by reaction of 2-
acetylnicotinic acid with 3,5-difluorobenzene-N-
2-methylsemicarbazone in the presence of pyr-
idyl tosylate [292].
Diflufenzopyr is a polar auxin-transport in-
hibitor. This systemic herbicide is used post-
emergence to control annual broad-leaved and
perennial weeds in a variety of crops. . .
Formulation. Granules, wetting granular
end-use product.
Trade Name. Distinct.
Diflufenzopyr decays with half-lives of 14, 17
and 24 d in soil, photolytically, and hydrolyti-
cally, respectively.
Dithiopyr [97886-45-8], S,S0 -dimethyl-2-
difluoromethyl-4-isobutyl-6-trifluoromethylpyr-
imidine-3,5-dicarbothioate, C15H16F5NO2S2, Mr
401.42, mp 65
C, log Kow 5.88, r 1.33 g/mL, it
consists of colorless crystals which are sparingly
soluble in water [1, 2, 293].
Dithiopyr is produced by dehydration of
diethyl 2,6-dihydro-2-difluoromethyl-6-trifluor-
omethyl-4-(2-methylisopropyl) piperidine dicar-
boxylate, followed by hydrolysis of the pyridine
dicarboxylate, and by treatment with sulfonyl
chloride and methanol [294].
Vol. 39
Dithiopyr is a cell-division inhibitor used pre-
and early post-emergence to control annual
grasses and broad-leaved weeds in turf, and
annual grasses in rice.
Formulation. Suspension concentrate, emul-
sifiable concentrate, granules.
Trade Names. Dictran, Dimension.
Dithiopyr decays with half-lives of 39 and
19 d in soil and photolytically, respectively. It is
stable towards hydrolysis.
Fluroxypyr-meptyl [81406-37-3], (RS)-
1-meptyl-4-amino-3,5-dichloro-6-fluoro-2-pyri-
dyloxyacetate, C15H21Cl2FN2O3, Mr 367.24, mp
59
C, log Kow 4.5, r 1.32 g/mL, vapor pressure
0.0013 mPa, is a gray to olive-colored crystalline
solid which is sparingly soluble in water, mod-
erately soluble in hexane, and fairly soluble in
dichloromethane, toluene, xylene, acetone,
methanol, and diethyl ether [13, 295, 296].
Fluroxypyr-meptyl is produced by reaction of
4-amino-3,5-dichloro-2-(methylsulfonyl)pyri-
dine with methyl glycolate [297].
Fluroxypyr-meptyl is absorbed by foliage and
produces characteristic auxin-type responses. It
is used post-emergence to control a number of
economically important broad-leaved weeds in
all small grains, in orchards, and in plantations.
Formulation. Emulsion concentrate.
Trade Names. Starane, Bastion T, Cabadex,
Forefront, Galaxy, Tomahawk.
Fluroxypyr-meptyl decays with half-lives of
3, 233, and 25 d in soil, hydrolytically, and in
water-sediment. It is stable towards photolytic
action.
Picloram [1918-02-1], 4-amino-3,5,6-tri-
chloropyridine-2-carboxylic acid, C6H3Cl3N2O2,
Mr 241.46, mp 215218
C (decomp.), log Kow
1.92, r 1.81 g/mL, pKa 2.3, vapor pressure 80
nPa, is a light brown to tan powder which is
sparingly soluble in water, n-heptane, xylene,
Weed Control, 2. Individual Herbicides 259
dichloromethane, benzene, and carbon disulfide,
and fairly soluble in acetone, ethanol, and diethyl
ether [13, 5, 298, 299].
Picloram is produced from a-picoline by chlo-
rination, followed by hydrolysis of the a-trichlor-
opicoline derivative, and amination [286].
Picloram is a selective, systemic herbicide
used to control most annual and perennial
broad-leaved weeds on grassland and noncrop
areas.
Formulation. Suspension concentrate.
Trade Names. Tordon, Galera, Tordone 101.
Picloram decays with half-lives of 90, 2, and
1961 d in soil, photolytically, and in water-sedi-
ment, respectively.
Picolinafen [137641-05-5], 40 fluoro-6-
(a,a,a-trifluoro-m-tolyloxy)pyridine-2-carbox-
anilide, C19H12F4N2O2, Mr 376.30, mp 107.2
107.6
C, log Kow 5.43, r 1.45 g/mL, vapor
pressure 0.17 mPa, is a colorless crystalline solid
which is practically insoluble in water, moder-
ately soluble in methanol, and soluble in acetone,
ethyl acetate, and toluene [2, 300, 301].
Picolinafen can be produced by reaction of 2-
(3-trifluoromethylphenoxy)nicotinic acid with 4-
fluoroaniline in the presence of sulfonyl chloride
[302].
Picolinafen is a selective herbicide, rapidly
absorbed by leaves, used post-emergence to con-
trol broad-leaved weeds in cereals, barley,
spring-wheat.
Formulation. Wettable powder, suspension
concentrate.
Trade Names. Flight, Orient, Pico, PicoMax,
Picina, Sniper, Paragon.
Picolinafen decays with half-lives of 30, 31,
and 6 d in soil, photolytically, and in water-
260 Weed Control, 2. Individual Herbicides
sediment, respectively. It is stable towards
hydrolysis.
Thiazopyr [117718-60-2], methyl 2-difluor-
omethyl-5-(4,5-dihydro-1,3-thiazol-2-yl)-4-isobu-
tyl-6-trifluoromethylnicotinate, C16H17F5N2O2S,
Mr 396.38, mp 77.379.1, log Kow 3.89, r
1.37 g/mL, vapor pressure 0.27 mPa, is a light tan
crystalline solid which is practically insoluble in
water, and readily soluble in acetone, methanol,
and hexane [13, 303].
Thiazopyr is produced by amination of 3-
chlorocarbonyl-5-carboxymethyl-4-(2-methyl-
propyl)-2-trifluoromethyl-6-difluoromethylpyri-
dine with ethanolamine, followed by treatment
with phosphorus oxytrichloride, and cyclization
[304].
Thiazopyr inhibits cell division, and is used
pre-emergence for the control of annual grasses
and some broad-leaved weeds in tree fruit, vines,
citrus, sugar cane, and pineapples.
Formulation. Emulsifiable concentrate,
granules, wettable powder.
Trade Names. Visor, technical, MON 13211.
Thiazopyr decays in soil with a half-life of
64 d.
Triclopyr [55335-06-3], 3,5,6-trichloro-2-
pyridyloxyacetic acid, C7H4Cl3NO3, Mr 256.5,
mp 150.5
C, log Kow 4.62, r 1.3 g/mL, pKa 3.97,
vapor pressure 0.1 mPa, is a fluffy, colorless
solid which is sparingly soluble in hexane, mod-
erately soluble in water and dichloromethane,
fairly soluble in toluene, and readily soluble in
acetone, acetonitrile, methanol, and ethyl acetate
[13, 305].
Triclopyr is produced by reaction of 2,3,5,6-
tetrachloropyridine with formaldehyde in di-
methyl sulfoxide containing potassium cyanide,
Vol. 39
followed by hydrolysis of the cyano compound to
the acid [306].
Triclopyr is a selective, systemic herbicide,
absorbed by roots and foliage, used for the con-
trol of woody plants, many broad-leaved weeds
in grassland, uncultivated land, industrial areas,
coniferous forest, plantation crops, and rice
fields. It belongs to the class of synthetic auxins.
Formulation. Emulsifiable concentrate.
Trade Names. Blaster T, Doxstar, Grazon 90,
Garlon Trident.
Triclopyr decays with half-lives of 39, 0.1,
8.7, and 29 d in soil, photolytically, hydrolyti-
cally, and in water-sediment, respectively.
1.12. (Thio)Carbamates
Asulam [3337-71-1], (sodium salt: [2302-17-
2]), methyl sulfanilylcarbamate, C8H10N2O4S, Mr
230.26, mp 142144
C, log Kow 0.27, r
1.418 g/mL, pKa 4.82, vapor pressure 0.192 mPa,
consists of colorless crystals which are moderately
soluble in water, hydrocarbons, and chlorinated
hydrocarbons, and soluble in acetone, methanol,
ethanol, methyl ethyl ketone, and dimethylforma-
mide [1, 2, 307].
Asulam is produced by reaction of 4-amino-
benzenesulfonamide, after protection of the ami-
no group, with ethyl chloroformate in the pres-
ence of a base [308].
Asulam, a cell-division inhibitor, is a selec-
tive, systemic herbicide, translocated, used for
the control of annual and perennial grasses and
broad-leaved weeds in a variety of crops, grass-
land, noncropland, and forestry.
Formulation. Soluble concentrate.
Trade Names. Asulox, Asilan, Sanulam, Jon-
nix, Asulfox.
Barban [101-27-9], 4-chlorobut-2-ynyl 3-
chlorocarbanilate, C11H9Cl2NO2, Mr 258.11, mp
7576
C, log Kow 3.41, r 1.39 g/mL, is a color-
less crystalline solid which is practically insolu-
ble in water, moderately soluble in n-hexane, and
soluble in benzene, n-butylbenzene, toluene, and
xylene [2, 3].
Vol. 39
Barban can be prepared by reaction of 4-
chloro-2-butyn-1-ol with chlorophenyl isocya-
nate [309].
Barban is a selective post-emergence herbi-
cide for general control of weeds in cereals (wild
oats)and sugarbeet, and control of canarygrass in
barley, flax, lentils, peas, sawflower, etc. It re-
duces plant cellular divisions.
Formulation. Emulsifiable concentrate.
Trade Name. Barban.
Barban decays with half-lives of 5 and 0.05 d
in soil and hydrolytically, respectively.
Butylate [2008-41-5], S-ethyl diisobutyl
(thiocarbamate), C11H23NOS, Mr 217.41, mp
137
C, bp 137.5138
C (2.8 kPa),log Kow
4.15, r 0.94 g/mL, vapor pressure 170 mPa, is
a yellow liquid which is slightly soluble in water,
and miscible with common organic solvents
[13].
[(CH3)2CHCH2]2NC(O)SCH2CH3
Butylate is produced by reaction of diisobu-
tylcarbamoyl chloride with ethylmercaptan
[310].
Butylate, which inhibits lipid metabolism, is a
selective, systemic herbicide used pre-planting
and soil-incorporated for the control of annual
grass weeds in maize, pineapples, etc.
Formulation. Emulsifiable concentrate,
granules.
Trade Names. Sutan Plus, Anelda,Genate
Plus, Sutazibe Plus.
Butylate decays in soil with a half-life of 40 d.
It is stable towards hydrolysis.
Carbetamide [16118-49-3], (R)-1-(ethyl-
carbamoyl)ethyl carbanilate, C12H16N2O3, Mr
236.27, mp 110
C, log Kow 1.67, r 1.18 g/mL,
pKa 11.3, vapor pressure 0.3 mPa, consists of
colorless crystalline powder which is fairly
soluble in water, moderately soluble in cyclo-
hexane, and readily soluble in acetone, ethanol,
methanol, ethyl acetate, and dimethylforma-
mide [1, 2].
Weed Control, 2. Individual Herbicides 261
Carbetamide is produced by condensation of
phenyl isocyanate with N-ethyl lactamide [311].
Carbetamide, a cell-division inhibitor, is a
selective herbicide with some residual activity,
absorbed by roots, used to control annual grasses
and some broad-leaved weeds in clover, some
vegetables, oilseed rape, vines, and fruit
orchards.
Formulation. Wettable powder, water-dis-
persible granules.
Trade Names. Leguram, Carbetamex,
Crawler.
Carbetamide decays with half-lives of 25, 19,
and 55.5 d in soil, hydrolytically, and in water-
sediment, respectively. It is stable towards
photolysis.
Chlorbufam [1967-16-4], (RS)-1-methyl-
prop-2-ynyl 3-chlorocarbanilate, C11H10ClNO2,
Mr 223.67, mp 4546
C, log Kow 3.02, r 1.22 g/
mL, vapor pressure 2.1 mPa, is a colorless crys-
talline solid which is sparingly soluble in water,
moderately soluble in ethanol, and soluble in
methanol and acetone [13].
Chlorbufam can be made by reaction of 3-
chlorophenyl isocyanate with 1-methylprop-2-
yn-1-ol, or with m-chloroaniline, phosgene, and
3-butyn-2-ol [3].
Chlorbufam is a selective, pre-emergence
herbicide used to control grasses and broad-
leaved weeds in onions, leeks, garlic, shallots,
beet, spinach, etc.
Formulation. Emulsifiable concentrate.
Trade Names. Grisemin, Grisin, Alipur.
Chlorbufam decays in soil with a half-life of
56 d.
Chlorpropham [101-21-3], isopropyl 3-
chlorocarbanilate, C10H12ClNO2, Mr 123.66, mp
41.442
C, log Kow 3.76, r 1.18 g/ml, vapor
pressure 24 mPa, is a colorless solid which is
262 Weed Control, 2. Individual Herbicides
moderately soluble in water, and readily soluble
in heptane, acetone, xylene, and dichloro-
methane [13, 312, 313].
Chlorpropham is produced by reaction of m-
chloroaniline with isopropyl chloroformate
[314].
Chlorpropham, a cell-division inhibitor, is a
selective herbicide with residual activity used
pre-emergence for the control of annual grasses
and some broad-leaved weeds in many crops; it is
also used to suppress sprouting of potatoes.
Formulation. Emulsifiable concentrate, dust,
granules.
Trade Names. Decco Aerosol 273, Prevenol.
Chlorpropham decays with half-lives of 25,
83, and 95 d in soil, photolytically, and in water-
sediment. It is stable towards hydrolysis.
Cycloate [1134-23-2], S-ethyl cyclohexyl
(ethyl)thiocarbamate, C11H21NOS, Mr 215.36,
mp 11.5
C, bp 145146
C (1.33 kPa), log Kow
4.11, r 1.02 g/mL, vapor pressure 830 mPa, is a
colorless liquid with an aromatic odor which is
sparingly soluble in water, and miscible with
most organic solvents [13, 315].
Cycloate is produced by reaction of N-cyclo-
hexyl-N-ethylcarbamoyl chloride with ethylmer-
captan [316].
Cycloate is a lipid-metabolism inhibitor, ab-
sorbed by roots, which is used pre-planting and
soil-incorporated for the control of annual grass
weeds and some perennial grasses and broad-
leaved weeds in sugar beet, fodder beet, spinach,
etc.
Formulation. Emulsifiable concentrate,
granules.
Trade Names. Ro-Neet, Sabet,.
Cycloate decays in soil and hydrolytically
with half-lives of 61 and 30 d, respectively.
Desmedipham [13684-56-5], ethyl 3-phe-
nylcarbamoyloxylcarbanilate, C16H16N2O4, Mr
Vol. 39
300.31, mp 118.5120
C, log Kow 3.39, r
1.32 g/mL, vapor pressure 0.041 mPa, forms
colorless crystals which are sparingly soluble in
water, moderately soluble in toluene, and soluble
in methanol and acetone [1, 2, 317, 318].
Desmedipham is produced by reaction of m-
aminophenol with ethyl chloroformate, followed
by treatment with phenyl isocyanate [319].
Desmedipham, a photosynthesis electron-
transport inhibitor, is a selective, systemic her-
bicide, absorbed by leaves, used post-emergence
to control broad-leaved weeds in beet crops, etc.
Formulation. Emulsifiable concentrate.
Trade Names. Betanal AM, Kemifam.
Desmedipham decays with half-lives of 8, 1,
and 3 d in soil, hydrolytically, and in water-
sediment, respectively. It is stable towards
photolysis.
Dimepiperate [61432-55-1], S-(1-methyl-
1-phenylethyl)piperidine-1-carbothioate,
C15H21NOS, Mr 263.39, mp 38.839.3
C, log
Kow 4.02, r 1.08 g/mL, vapor pressure 0.53 mPa,
is a waxlike solid which is sparingly soluble
in water, and soluble in acetone, chloroform,
cyclohexanone, ethanol, toluene, and hexane
[1, 2].
Dimepiperate is produced by reaction of ben-
zene isopropylmercaptan with piperidine carba-
moyl chloride [316].
Dimepiperate, a lipid-metabolism inhibitor,
is a systemic herbicide, translocated, used for
the control of Echinochloacrus galli in flooded
rice.
Formulation. Emulsifiable concentrate,
emulsifiable granules.
Trade Names. Yakamate, Yukamato.
Dimepiperate decays with a half-life of 7 d in
soil.
EPTC [759-94-4], S-ethyl dipropyl(thiocar-
bamate), C9H19NOS, Mr 189.3, bp 127
C (2.66
kPa), log Kow 3.2, r 0.96 g/mL, vapor pressure
Vol. 39
4.5 Pa, is a pale yellow liquid which is sparingly
soluble in water, and miscible with acetone,
benzene, xylene, and ethanol [13].
(CH3CH2CH2)2NC(O)SCH2CH3
EPTC is produced by reaction of di-n-propy-
lamine with phosgene, followed by treatment
with ethyl mercaptan [320].
EPTC, a lipid-metabolism inhibitor, is a
selective herbicide, absorbed by shoots and
roots, used pre-planting with soil incorporation
for the control of annual and perennial grasses
and some broad-leaved weeds in many crops.
Formulation. Emulsifiable concentrate,
granules,
Trade Names. Eptam, Eradicane, Alirox .
EPTC decays with half-lives of 6 and 300 d in
soil and hydrolytically, respectively.
Esprocarb [85785-20-2], S-benzyl (RS)-
1,2-dimethylpropyl(ethyl)thiocarbamate,
C15H23NOS, Mr 265.4, mp 25
C, bp 135
C (4.6
kPa), log Kow 4.6, r 1.03 g/mL, vapor pressure
10.1 mPa, is a liquid which is sparingly soluble in
water, and fairly soluble in ethanol, chloroform,
xylene, acetone, and acetonitrile [1, 2].
Esprocarb is produced by reaction of N-ethyl-
N-(methyl)isobutylcarbamoyl chloride with
mercaptotoluene [316].
Esprocarb is a lipid-metabolism inhibitor,
which is used pre- and post-emergence for the
control of annual weeds and Echinocloa sp. in
paddy rice.
Formulation. 95% technical.
Trade Names. Fujigrass, Sparkstar, Esprocarb.
Esprocarb decays in soil with a half-life of
50 d. It is stable towards photolysis and
hydrolysis.
Karbutilate [4849-32-5], 3-(3,3,-dimethy-
lureido)phenyl tert-butylcarbamate, C14H21N3O3,
Mr 279.33, mp 176176.5
C, r 3.0 g/mL, vapor
pressure 6.0 nPa, is a colorless crystalline solid
which is sparingly soluble in water, moderately
soluble in acetone, xylene, and soluble in dimethyl-
formamide [2].
Weed Control, 2. Individual Herbicides 263
Karbutilate can be made by reaction of m-
aminophenol with N,N-dimethylcarbamoyl chlo-
ride followed by reaction with N-tert-butylcar-
bamoyl chloride [54].
Karbutilate is a nonselective herbicide, ab-
sorbed mainly by roots, used as growth regulator
and desiccant on various weeds and grasses.
Formulation. Granules, wettable powder.
Trade Names. Tanzene, Tandex.
Molinate [2212-67-1], S-ethyl azepane-1-
carbothioate, C9H17NOS, Mr 187.31, mp 25
C, bp 136.5
C (1.33 kPa), log Kow 2.86, r
1.05 g/mL, vapor pressure 500 mPa, is a color-
less liquid which is moderately soluble in water,
and miscible with methanol, acetone, ethyl ace-
tate, and hexane [13, 321, 322].
Molinate is produced by reaction of ethyl
chlorothioformate with hexamethyleneimine
[323].
Molinate, a lipid-metabolism inhibitor, is a
selective, systemic herbicide, absorbed by roots
and translocated, used to control germinating
broad-leaved weeds and grasses, and is applied
either before planting, to water-seeded, shallow-
soil-seeded, or post-flood rice.
Formulation. Granules, emulsifiable liquid,
technical.
Trade Names. Ordram, Sakkimol,
Molinate decays with half-lives of 28 and
365 d in soil and hydrolytically, respectively. It
is stable towards photolysis.
Orbencarb [34622-58-7], S-2-chloroben-
zyl diethylthiocarbamate, C12H16ClNOS, Mr
257.78, mp 20
C, bp 150152
C (133 Pa),
log Kow 4.17, r 1.18 g/mL, vapor pressure
4.26 mPa, is a colorless liquid which is sparing-
ly soluble in water, and readily soluble in meth-
anol, dichloromethane, acetone, and n-hexane
[1, 2].
264 Weed Control, 2. Individual Herbicides
Orbencarb is produced by reaction of 2-chlor-
omercaptotoluene with N-diethylcarbamoyl
chloride [54].
Orbencarb is a selective herbicide used pre-
emergence to control broad-leaved weeds and
annual grasses in barley, wheat, rye, maize, soya
beans, cotton, and turf.
Formulation. Emulsifiable concentrate.
Trade Names. Lanray, Golaprex.
Orbencarb decays photolytically with a half-
life of 1.5 d. It is stable towards hydrolysis.
Pebulate [1114-71-2], S-propyl butyl(eth-
yl)thiocarbamate, C10H21NOS, Mr 203.34, bp
142
C (2.6 kPa), log Kow 4, r 0.96 g/ml; vapor
pressure 0.009 mPa, is a colorless to yellow
liquid which is moderately soluble in water, and
miscible with acetone, benzene, toluene, and
xylene [13, 324].
Pebulate is produced by reaction of ethylbu-
tylamine with phosgene, followed by treatment
with propyl mercaptan [325].
Pebulate, an inhibitor of the biosynthesis of
very long chain fatty acids, is a selective, sys-
temic herbicide used pre-emergence and soil-
incorporated to control annual grasses and some
broad-leaved weeds in sugar beet, tomatoes, etc.
Formulation. Emulsifiable concentrate,
granules.
Trade Name. Tillam.
Pebulate decays in soil with a half-life of
17.5 d.
Phenmedipham-methyl [13684-63-4],
methyl 3-(3-methylcarbaniloyloxy)carbamate,
C16H16N2O4, Mr 300.31, mp 143144
C, log
Kow 3.59, r 1.36 g/mL, vapor pressure 0.7 nPa,
forms colorless crystals which are sparingly sol-
uble in water, moderately soluble in methanol,
ethyl acetate, benzene, chloroform, soluble in
acetone, cyclohexanone [13, 326, 327].
Vol. 39
Phenmedipham-methyl is produced by reac-
tion of 3-aminotoluene with 3-methylcarbamoyl-
benzoyl chloride [319].
Phenmedipham-methyl, a photosynthesis
electron-transport inhibitor, is a selective, sys-
temic herbicide used post-emergence for the
control of most annual broad-leaved weeds in
beet crops, strawberries, peas, spinach, etc.
Formulation. Suspension concentrate, emul-
sifiable concentrate.
Trade Names. Betanal, Alegro, Beetup,
Pump, Twin.
Phenmedipham-methyl decays with half-
lives of 18, 0.5 and 0.12 d in soil, hydrolytically,
and in water-sediment, respectively. It is stable
towards photolysis.
Propham [122-42-9], isopropyl carbani-
late, C10H13NO2, Mr 179.22, mp 8790
C, bp
sublimes on heating, log Kow 2.6, r 1.09 g/mL,
vapor pressure 1.999 Pa, forms colorless crystals
which are sparingly soluble in water, and soluble
in esters, alcohols, acetone, benzene, xylene
[13, 328].
Propham can be synthesized by reaction of
phenyl isocyanate with isopropyl alcohol, or of
aniline with isopropyl chloroformate [329].
Propham is a selective, systemic herbicide
used pre- and post-emergence, and by pre-plant
incorporation, to control grasses and broad-
leaved weeds on forage crops, flax, lettuce, sugar
beets, peas, etc. It is also used to prevent spouting
of potatoes. It inhibits mitosis.
Formulation. Granules, wettable powder,
emulsifiable concentrate.
Trade Names. Premalox, Agermin, Collavin.
Propham decays with half-lives of 11, 32,
1000, and 42 d in soil, photolytically, hydrolyti-
cally, and in water-sediment, respectively.
Prosulfocarb [52888-80-9], S-benzyl di-
propylthiocarbamate, C14H21NOS, Mr 251.39,
mp 20
C, bp 341
C, log Kow 4.48, r
Vol. 39
1.04 g/mL, vapor pressure 0.79 mPa, is a pale
straw colored liquid which is sparingly soluble in
water, and miscible with acetone, chloroform,
chlorobenzene, ethanol, xylene, and ethyl acetate
[1, 2, 330, 331].
Prosulfocarb is produced by reaction of N-
dipropylcarbamoyl chloride with mercaptoto-
luene [316].
Prosulfocarb is a lipid-metabolism inhibitor,
and is a selective herbicide, absorbed by leaves
and roots, used pre- and early post-emergence for
the control of a wide range of grass and broad-
leaved weeds in winter wheat, winter barley, and
rye.
Formulation. Emulsifiable concentrate.
Trade Names. Boxer, Defy.
Prosulfocarb decays with half-lives of 31 and
214 d in soil and water-sediment, respectively. It
is stable towards photolysis and hydrolysis.
Pyributicarb [88678-67-5], O-3-tert-butyl-
phenyl 6-methoxy-2-pyridyl(methyl)thiocarba-
mate, C18H22N2O2S, Mr 330.44, mp 85.7
86.2
C, log Kow 5.18, vapor pressure 266 mPa,
forms colorless crystals which are sparingly sol-
uble in water, fairly soluble in methanol and
ethanol, and readily soluble in acetone, xylene,
chloroform, and ethyl acetate [13].
Pyributicarb is produced by reaction of 3-tert-
butylphenol with 6-methoxy-2-N-methyl-N-
thionyl chloride [332].
Pyributicarb is a systemic herbicide used pre-
and early post-emergence for the control of
annual and perennial grasses and weeds in turf.
Formulation. 95% technical.
Trade Names. Eigen, Isshintasuke.
Thiobencarb [28249-77-6], S-4-chloroben-
zyl diethylthiocarbamate, C12H16ClNOS, Mr
257.8, bp 326.6
C, log Kow 4.23, r 1.16 g/mL,
vapor pressure 2.39 mPa, is a pale yellow to
colorless viscous liquid which is sparingly soluble
Weed Control, 2. Individual Herbicides 265
in water, and readily soluble in acetone, ethanol,
xylene, methanol, benzene, and acetonitrile [13].
Thiobencarb is produced by reaction of p-
chloromercaptotoluene with N-diethylcarba-
moyl chloride [316].
Thiobencarb is a protein-synthesis inhibitor,
and is a selective herbicide used pre- and early
post-emergence for the control of a number of
grasses and weeds in rice.
Formulation. Emulsifiable concentrate,
granules.
Trade Names. Saturn, Bigturn, Bolero.
Thiobencarb decays with half-lives of 21 and
95 d in soil and water-sediment, respectively. It
is stable towards photolysis and hydrolysis.
Triallate [2303-17-5], S-2,3,3-trichloroal-
lyl diisopropyl(thiocarbamate), C10H16Cl3NOS,
Mr 304.7, mp 2930
C, bp 279
C, log Kow 4.04,
r 1.27 g/mL, vapor pressure 12 mPa, is a color-
less solid which is sparingly soluble in water, and
readily soluble in acetone, ethanol, methanol,
and xylene [13, 333335].
[(CH3)2CH]2NC(O)SCH2C(Cl)CCl2
Triallate is produced by reaction of isopropy-
lamine with phosgene, followed by coupling with
1,1-dichloro-2-chloro-3-mercapto-1-propylene
[336].
Triallate inhibits fatty acid and lipid biosyn-
thesis, and is a selective herbicide used pre- or
post-planting and soil-incorporated for the con-
trol of wild oats and some annual grasses in
wheat, barley, rye, field beans, etc.
Formulation. Emulsifiable concentrate,
granules.
Trade Names. Abrade BW, Far-Go, Avadex
Excel.
Triallate decays with half-lives of 82 and 57 d
in soil and water-sediment, respectively. It is
stable towards photolysis and hydrolysis.
Vernolate [1929-77-7], S-propyl dipro-
pylthiocarbamate, C10H12NOS, Mr 203.34, bp
149150
C (3.99 kPa), log Kow 3.84, r
0.95 g/mL, vapor pressure 1.39 Pa, is a color-
less liquid which is sparingly soluble in water,
266 Weed Control, 2. Individual Herbicides
and miscible with common organic solvents
[13].
(CH3CH2CH2)2NC(O)SCH2CH2CH3
Vernolate is produced by reaction of N-dipro-
pylcarbamoyl chloride with propylmercaptan
[316].
Vernolate inhibits lipid metabolism, and is a
selective herbicide used soil-incorporated, either
pre-planting or post-emergence, for the control
of germinating broad-leaved weeds and grasses
in peanuts, maize, soya beans, tobacco, sweet
potatoes, etc.
Formulation. Emulsifiable concentrate,
granules, emulsifiable liquid.
Trade Names. Vernam, Surpass.
Vernolate decays in soil with a half-life of
16 d.
1.13. Organophosphates
Anilofos [64249-01-0], S-(4-chloro-N-iso-
propylcarbaniloxymethyl)-O,O-dimethyl phos-
phorodithioate, C13H19ClNO3PS2, Mr 367.85, mp
50.552.5
C, log Kow 3.81, r 1.27 g/mL, vapor
pressure 2.2 mPa, is a colorless crystalline solid
which is sparingly soluble in water, and readily
soluble in acetone, chloroform, toluene, benzene,
ethanol, dichloromethane, and ethyl acetate [1, 2].
Anilofos is produced by reaction of O,O-
dimethylphosphorodithioate with p-chloroben-
zene-N-isopropylcarbamoyl chloride [337].
Anilofos is a selective herbicide, absorbed
mainly through roots, used to control annual
grasses and sedges in transplanted rice. It inhibits
cell division.
Formulation. Technical, emulsifiable con-
centrate.
Trade Names. Arizon, Rico, Anilogard,.
Anilofos decays in soil with a half-life of 38 d.
It is stable towards photolysis and hydrolysis.
Bensulide [741-58-2], O,O-diisopropyl S-
2-phenylsulfonylaminoethyl phosphorodithio-
ate, C14H24NO4PS2, Mr 397.51, 34.4
C, log Kow
Vol. 39
4.2, r 1.25 g/mL, vapor pressure 0.133 mPa, is a
colorless crystalline solid or a colorless viscous
liquid which is sparingly soluble in water, and
readily soluble in acetone, ethanol, and xylene
[13, 338].
Bensulide is produced by reaction of O,O-
diisopropylphosphorodithioate with N-chlor-
oethylbenzene sulfonamide [339].
Bensulide is a selective herbicide used pre-
emergence on cotton, on some vegetables, and
also on established turf. It inhibits germination of
seeds.
Formulation. Granules, emulsifiable
concentrate.
Trade Names. Betasan, Prefar, Bensumac,
Pre-San, Lawnpur.
Bensulide decays with half-lives of 90 and
200 d in soil and hydrolytically, respectively.
Bilanafos (Bialaphos) [35597-43-4], (S)-
2-amino-4-[hydroxy(methyl)phosphinoyl]bu-
tyryl-L-alanyl-L-alanine, C11H22N2O6P, Mr
323.28, mp 159161
C, log Kow 2.06,d
1.33 g/mL, is a colorless solid which is moder-
ately soluble in water, soluble in ethanol, meth-
anol, and practically insoluble in organic sol-
vents [1, 2].
Bilanafos is produced by Streptomyces hygro-
scopius, which is used as a natural source for its
production [340].
Bilanafos, a glutamine-synthase inhibitor, is
a nonselective, systemic herbicide with contact
activity, used post-emergence for the control of
annual weeds in vines, apples, brassicas, rub-
ber, etc. It is also used to control annual and
perennial weeds in uncultivated land. It is
usually employed as the sodium salt [71048-
99-2].
Formulation. Water-soluble powder, liquid.
Trade Names. Bialaphos Meiji, Herbiace,
Herbie.
Vol. 39
Butamifos [36335-67-8], (RS)-{O-ethyl-O-
6-nitro-m-tolyl [(RS)-sec-butyl]phosphorami-
dothioate}, C13H21N2O4PS, Mr 332.4, log Kow
4.62, r 1.19 g/mL, vapor pressure 84 mPa,is a
yellow-brown liquid which is moderately soluble
in water, and readily soluble in acetone, metha-
nol, and xylene [1].
Butamifos is produced by reaction of 2-nitro-
5-methylphenol with O-ethyl-N-sec-butylpho-
sphoramidothionyl chloride [341].
Butamifos is a selective, nonsystemic herbi-
cide used pre-emergence to control annual weeds
in beans, rice, vegetables, etc.
Formulation. Emulsifiable concentrate, wet-
table powder, granules.
Trade Name. Cremart.
Fosamine [59682-52-9], ethyl hydrogen
carbamoylphosphonate, C3H8NO4P, Mr 153.07,
mp 174
C, log Kow 2.9, r 1.24 g/mL, pKa 9.25,
vapor pressure 0.53 mPa, is a colorless crystal-
line solid which is practically insoluble in ace-
tone, moderately soluble in benzene and ethanol,
and soluble in methanol and water [13].
Fosamine can be prepared by reaction of
triethyl phosphate with methyl chloroformate
and ammonia [342].
Fosamine is a slightly systemic herbicide with
contact activity not used on food or field crops but
to control brushes. It is used to prevent dormant
tissue from becoming active and growing again.
Mostly the ammonium salt [25954-13-6] is used.
Formulation. Liquid.
Trade Names. Krenite, DPX-1108.
Fosamine decays in soil with a half-life of 8 d.
It is stable towards hydrolysis.
Glufosinate-ammonium [77182-82-2],
ammonium (2RS)-2-amino--4-y(methylphosphi-
nato)butyric acid, C5H15N2O4P, Mr 198.2, mp
Weed Control, 2. Individual Herbicides 267
216.5
C, log Kow 4.01, r 1.32 g/mL, pKa1 <2,
pKa2 2.9, pKa3 9.8, vapor pressure 0.031 mPa,
forms a colorless crystalline solid which is readi-
ly soluble in water and methanol, and moderately
soluble in acetone, ethanol, ethyl acetate, tolu-
ene, and hexane [13].
Glufosinate-ammonium is produced by reac-
tion of O,O-diethylmethylphosphonate with 2-
amino-4-bromobutanoic acid [342].
Glufosinate-ammonium, a glutamine-
synthase inhibitor, is a nonselective contact her-
bicide with some systemic activity used for the
control of a wide range of annual and perennial
broad-leaved weeds and grasses in fruit orchards,
vineyards, rubber and oil palm plantations, orna-
mental trees and brushes, noncropland, and pre-
emergence in vegetables.
Formulation. Suspension concentrate,
liquid.
Trade Names. Basta, Liberty,. Ignite, Hra-
vest, Kaspar.
Glufosinate-ammonium decays with half-
lives of 7.4, 300, and 24.5 d in soil, hydrolytical-
ly, and in water-sediment, respectively. It is
stable towards photolytic action.
Glyphosate [1071-83-6], N-(phophono-
methyl)glycine, C3H8NO5P, Mr 169.1, mp
189.5
C, log Kow <3.2, r 1.705 g/mL, pKa
2.34, vapor pressure 0.0013 mPa, forms color-
less crystals which are fairly soluble in water, and
practically insoluble in common organic solvents
[13].
Glyphosate is produced by heating a mixture
of phosphorous acid and a-amino acetic acid, and
then adding formaldehyde [343].
Glyphosate inhibits enolpyruvylshikimi-3-
phosphate synthase and is a nonselective, sys-
temic herbicide with contact activity used pre-
harvest, post-planting/pre-emergence to control
annual and perennial grasses and broad-leaved
weeds in stubble, cereals, peas, beans, oilseed
rape, flax, mustard, etc.
268 Weed Control, 2. Individual Herbicides
Formulation. Soluble concentrate, soluble
granules.
Trade Names. Rodeo, Roundup, Sting,
Touchdown, Barbaran, Sanos.
Glyphosate decays with half-lives of 12, 69, and
87 d in soil, photolytically, and in water-sediment,
respectively. It is stable towards hydrolysis.
Piperophos [24151-93-7], S-2-methylpi-
peridinocarbonylmethyl O,O-dipropyl phos-
phorodithioate, C14H28NO3PS2, Mr 353.48, mp
25
C, bp > 250
C, log Kow 4.3, r 1.13 g/mL,
vapor pressure 0.032 mPa, is a pale yellow
slightly viscous liquid which is practically insol-
uble in water, and miscible with benzene, hexane,
acetone, dichloromethane, and ethanol [1, 2].
Piperophos is produced by reaction of O,O-
diisopropylphosphorodithioate with 1-methylpi-
peridinylcarboxy chloride [344].
Piperophos is a selective, systemic herbicide,
absorbed by roots and foliage, used to control
annual grasses and sedges in directly seeded or
transplanted rice. It inhibits cell division.
Formulation. Microgranules.
Trade Names. Rilof Avirosan.
Piperophos decays in soil with a half-life of
30 d. It is stable towards photolysis and hydrolysis.
1.14. Cyclohexene Oximes
Alloxydim [55634-91-8], methyl (1R,S)-3-
[(E)-1-(allyloxyimino)butyl]-4-hydroxy-6,6-di-
methyl-2-oxocyclohex-3-enecarboxylate,
C17H25NO5, Mr 323.38, mp 185.5
C (decomp.),
log Kow 0.2, r 1.10 g/mL, vapor pressure
0.133 mPa, forms colorless crystals which are
readily soluble in water, dimethylformamide,
and methanol, and fairly soluble in ethanol,
methyl ethyl ketone, acetone, cyclohexanone,
ethyl acetate, and xylene [1, 2].
Vol. 39
Alloxydim is produced by reaction of mesityl
oxide with dimethyl malonate; the resultant prod-
uct is then treated with n-butyryl chloride, fol-
lowed by reaction with hydroxyallylamine [345].
Alloxydim inhibits mitosis and fatty acid
synthesis, and is a selective, systemic herbicide
used post-emergence for the control of grass
weeds and volunteer cereals in sugar beet, vege-
tables, and broad-leaved crops.
Formulation. Water-soluble powder.
Trade Names. Clout, Kusagard, Frevin.
Alloxydim decays with half-lives of 7, 0.22,
15, and 49 d in soil, photolytically, hydrolytical-
ly, and in water-sediment, respectively.
Butroxydim [138164-12-2], (5RS)-5-(3-
butyryl-2,4,6-trimethylphenyl)-2-[(EZ)-1-(etho-
xyimino)propyl-3-hydroxycyclohex-2-en-1-one,
C24H33NO4,Mr 399.52, mp 80
C, log Kow 1.9, r
1.2 g/mL, pKa 4.36, vapor pressure 0.001 mPa, is
an almost colorless powdery solid which is spar-
ingly soluble in water, moderately soluble in
hexane, methanol, and soluble in dichloro-
methane, acetone [1, 2].
Butroxydim is produced by reaction of
5-(2,4,6-trimethylphenyl)-2-(1-ethoxyimino)-3-
hydroxycyclohex-2-enone with butanoic acid
chloride in the presence of aluminum trichloride
[346].
Butroxydim is a post-emergence grass herbi-
cide used on broad-leaved crops.
Formulation. Water-dispersible granules.
Trade Name. Falcon.
Butroxydim decays with half-lives of 9 and
240 d in soil and hydrolytically, respectively.
Clethodim [99129-21-2], ()-(5RS)-2-
{(E)-1-[(2E)-3-chloroallyloxyimino]propyl}-5-
[(2RS)-2-(ethylthio)propyl]-3-hydroxycyclo-
hex-2-en-1-one, C17H26ClNO3S, Mr 359.92, mp
80
C, log Kow 4.14, r 1.16 g/ml, pKa 4.47,
vapor pressure 3.5 nPa, is an amber-colored
liquid which is moderately soluble in water, and
soluble in xylene, methanol, acetone, and ethyl
acetate [1, 2].
Vol. 39
Clethodim is produced by reaction of ethyl
mercaptan with crotonal, followed, successively,
by treatment with acetone, dimethyl malonate,
hydrolysis reagents, propionic acid chloride, and
a-chlorohydroxyallylamine [347].
Clethodim, a fatty acid synthesis inhibitor, is a
systemic herbicide used post-emergence for the
control of annual and perennial grasses in a wide
range of broad-leaved crops, vegetables, trees,
and vines.
Formulation. Emulsifiable concentrate, sus-
pension concentrate.
Trade Names. Select, Centurion.
Clethodim decays with half-lives of 3, 5.5,
and 23 d in soil, photolytically, and in water-
sediment, respectively.
Cycloxydim [101205-02-1], (5RS)-2-[(EZ)-
1-(ethoxyimino)butyl]-3-hydroxy-5-[(3RS)-thian-
3-yl]cyclohex-2-en-1-one, C17H27NO3S, Mr
325.46, mp 3941
C, log Kow 1.36, r 1.12 g/mL,
pKa 4.17, vapor pressure 0.01 mPa, consists of
colorless crystals which are sparingly soluble in
water, readily soluble in acetone, ethanol, dichlor-
omethane, and ethyl acetate, and soluble in n-
hexane [1, 2].
Cycloxydim is produced by reaction of 2-
butyryl-5-(thian-3-yl-1,3-cyclohexanedione
with hydroxyethylamine [348].
Cycloxydim, which inhibits fatty acid syn-
thesis, is a selective herbicide used post-emer-
gence to control annual and perennial grasses in
broad-leaved crops. It inhibits acetyl CoA
carboxylase.
Formulation. Emulsifiable concentrate.
Trade Names. Focus, Laser, Stratos.
Cycloxydim decays with half-lives of 5, 0.05,
172, and 32 d in soil, photolytically, hydrolyti-
cally, and in water-sediment, respectively.
Weed Control, 2. Individual Herbicides 269
Profoxydim [139001-49-3], (5RS)-2-{(EZ)-
1-[(2RS)-2-(4-chlorophenoxy)propoxyimino]bu-
tyl}-3-hydroxy-5-[(3RS)-thian-3-yl]cyclohex-2-
en-1-one, C24H32ClNO4S, Mr 466.03, bp decomp.
log Kow 3.9, r 1.2 g/mL, pKa 5.91, vapor pressure
0.17 mPa, is a colorless liquid which is practically
insoluble in water, and soluble in acetone and
ethyl acetate [2].
Profoxydim can be synthesized by reaction of
2-butyryl-5-(2-thian-3-yl)-1,3-cyclohexanedione
with 2-(4-chlorophenoxy)hydroxybutylamine, in
analogy to cycloxydim [348].
Profoxydim is a selective, systemic herbicide
used post-emergence to control grass weeds in
rice. It is an acetyl CoA carboxylase inhibitor.
Formulation. Emulsifiable concentrate.
Trade Names. Profoxydim, Clefoxydim.
Profoxydim decays with half-lives of 8, 140,
and 47 d in soil, hydrolytically, and in water-
sediment, respectively.
Sethoxydim [74051-80-2], (5RS)-2-[(EZ)-1-
(ethoxyimino)butyl]-5-[(2RS)2-(ethylthio)propyl]-
3-hydroxycyclohex-2-en-1-one, C17H29NO3S, Mr
327.48, bp > 90
C (3.99 mPa), log Kow 1.65, r
1.04 g/mL, pKa 4.58, vapor pressure 0.013 mPa,is
an oily amber-colored liquid which is sparingly
soluble in water, and readily soluble in most organic
solvents [13].
Sethoxydim is produced by reaction of ethyl
mercaptan with crotonal, followed by reaction
with acetone, dimethyl malonate, hydrolysis re-
agents, butyryl chloride, and hydroxyethylamine
[347].
Sethoxydim, which inhibits fatty acid synthe-
sis, is a selective herbicide used to control annual
270 Weed Control, 2. Individual Herbicides
and perennial grasses in broad-leaved crops. It is
an acetal CoA synthase inhibitor.
Formulation. Emulsifiable concentrate.
Trade Names. Naba, Fervinal, Poaset.
Sethoxydim decays with half-lives of 1.2,
0.02, 242, and 130 d in soil, photolytically,
hydrolytically, and in water-sediment,
respectively.
Tepraloxydim [149979-41-9], (5RS)-2-
{(EZ)-1-[(2E)-3-chloroallyloxyimino]propyl}-
3-hydroxy-5-perhydropyran-4-ylcyclohex-2-en-
1-one, C17H24ClNO4, Mr 341.8, mp 74
C, log
Kow 0.2, r 1.28 g/mL, pKa 4.58, vapor pressure
0.011 mPa, is a colorless powder which is spar-
ingly soluble in water, moderately soluble in n-
heptane, and soluble in ethyl acetate, acetone,
and methanol [1, 2, 349].
Tepraloxydim is prepared by condensation of 5-
perhydropyranyl-3-hydroxy-2-carbonylpropylcy-
clohex-2-ene-1-one with chloroallyloxyamine
[350].
Tepraloxydim is a broad-spectrum herbicide,
absorbed by leaves and translocated, used to
control grasses and broad-leaved weeds in soya
beans and cotton . It inhibits acetyl CoA
synthase.
Formulation. Emulsifiable concentrate.
Trade Names. Aramo, Standon, Tonga.
Tepraloxydim decays with half-lves of 10,
1.5, and 436 d in soil, photolytically, and hydro-
lytically, respectively.
Tralkoxydim [87820-88-0], (RS)-2-[(EZ)-
1-(ethoxyimino)propyl]-3-hydroxy-5-mesityl-
cyclohex-2-en-1-one, C20H27NO3, Mr 329.3, mp
110
C, log Kow 2.1, r 1.16 g/mL, pKa 4.3, vapor
pressure 0.37 mPa, consists of colorless crystals
which are sparingly soluble in water and hexane,
moderately soluble in methanol and acetone, and
readily soluble in ethyl acetate, toluene, and
dichloromethane [13, 351].
Vol. 39
Tralkoxydim is produced by condensation of
2,4,6-trimethylbenzaldehyde with acetone, fol-
lowed by condensation with diethyl malonate,
acylation with propionic acid anhydride, and
treatment with thioxyamine [352].
Tralkoxydim, an inhibitor of cell division and
fatty-acid synthesis, is a selective, systemic her-
bicide used pre-emergence for the control of
Avena sp. and other grass weeds in wheat, barley,
and grass seed crops.
Formulation. Emulsifiable concentrate, wa-
ter-dispersible granules, suspension concentrate.
Trade Names. Achieve, Grasp, Fleck,
Strimma.
Tralkoxydim decays with half-lives of 1.9, 5.8,
140, and 110.7 d in soil, photolytically, hydrolyt-
ically, and in water-sediment, respectively.
1.15. (Benzo)nitriles
Bromoxynil [1689-84-5], 3,5-dibromo-4-
hydroxybenzonitrile, C7H3Br2NO2, Mr 276.9,
mp 194195
C, log Kow 1.04, r 1.63 g/mL, pKa
3.86, vapor pressure 0.17 mPa, is a colorless
solid which is sparingly soluble in water, fairly
soluble in methanol, ethanol, and benzene, and
readily soluble in dimethylformamide, tetrahy-
drofuran, and acetone [13, 353].
Bromoxynil is produced by reaction of sodi-
um hypobromide with 4-hydroxybenzonitrile
[354].
Bromoxynil is a selective contact herbicide
used post-emergence to control annual broad-
leaved weeds in cereals, maize, sorghum, onions,
garlic, mint, turf, noncropland, etc. It is a photo-
system II inhibitor.
Formulation. Emulsifiable concentrate, sus-
pension concentrate, wettable powder.
Vol. 39
Trade Names. Brominal, Buctril, Bromox,
Bromoxan, Emblem, Kaleis.
Bromoxynil decays with half-lives of 1, 0.5,
and 13 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
Dichlobenil [1194-65-6], 2,6-dichloroben-
zonitrile, C7H3Cl2N, Mr 172.01, mp 144146
C,
bp 270
C, log Kow 2.74, r 1.40 g/mL, vapor
pressure 88 mPa, forms colorless crystals which
are sparingly soluble in water, fairly soluble in
acetone, dioxane, benzene, dichloromethane, xy-
lene, and ethanol, and soluble in dichloro-
methane [13].
Dichlobenil is produced by conversion of
2,6-dichlorotoluene into 2,6-dichlorobenzal
chloride, which is converted into 2,6-dichloro-
benzaldehyde, 2,6-dichlorobenzaldoxime, and
2,6-dichlorobenzonitrile [355].
Dichlobenil, a cellulose-biosynthesis inhibi-
tor, is a systemic herbicide used for selective
weed control of many annual perennial weeds in
woody ornamentals, fruit orchards, vineyards,
brush fruit, forest plantations, etc.
Formulation. Granules.
Trade Names. Sibenil, Osorno, Caseron.
Dichlobenil decays with half-lives of 70, 6,
and 150 d in soil, photolytically, and hydrolyti-
cally, respectively.
Ioxynil [1689-83-4], 4-hydroxy-3,5-diiodo-
phenyl cyanide, C7H3I2NO, Mr 370.91, mp 212
213
C, log Kow 2.2, r 2.72 g/mL, pKa 4.1, vapor
pressure 0.0024 mPa, is a colorless solid which is
sparingly soluble in water, fairly soluble in ace-
tone, ethanol, methanol, and chloroform, and
readily soluble in cyclohexanone, tetrahydrofu-
ran, and dimethylformamide [13, 356].
Ioxynil is produced by iodination of 4-hydro-
xybenzonitrile with iodine monochloride [354].
Weed Control, 2. Individual Herbicides 271
Ioxynil is a systemic, selective herbicide with
contact activity, used post-emergence to control
a wide range of annual broad-leaved weeds in
cereals, leeks, onions, garlic, on lawns, and on
newly sown turf. It inhibits photosystem II.
Formulation. Emulsifiable concentrate.
Trade Names. Actril, Totril, Sanoxynil, Trio-
nyl etc.
Ioxynil decays with half-lives of 6, 5, and 4.6 d
in soil, photolytically, and in water-sediment,
respectively. It is stable towards hydrolysis.
Pyraclonil [158353-15-2], 1-(3-chloro-
4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-
[methyl(prop-2-ynyl)amino]pyrazolo-4-carboni-
trile, C15H15ClN6, Mr 314.78, mp 9395
C, log
Kow 1.61, r 1.34 g/mL, vapor pressure 0.19 mPa, is
a colorless solid which is sparingly soluble in water
[2, 357, 358].
Pyraclonil is a post-emergence herbicide used
in rice to control grasses and broad-leaved weeds.
It inhibits protoporphyrinogen oxidase.
Formulation. Granules, emulsifiable powder.
Trade Name. Sunshine.
Pyraclonil decays with a half-life of 320 d
photolytically.
1.16. Triazinones
Hexazinone [51235-04-2], 3-cyclohexyl-6-
dimethylamino-1-methyl-1,3,5-triazine-2,4
(1H,3H)-dione, C12H20N4O2, Mr 252.31, mp 115
117
C, log Kow 1.17, r 1.25 g/mL, pKa 2.2,
vapor pressure 0.03 mPa, forms colorless crystals
which are fairly soluble in water and hexane,
readily soluble in chloroform, methanol, benzene,
dimethylformamide, acetone, and toluene [1, 2].
272 Weed Control, 2. Individual Herbicides
Hexazinone is produced by reaction of cya-
noamine with methyl chloroformate, followed by
methylation, and treatment with dimethylamine
and cyclohexyl isocyanate [359].
Hexazinone, which inhibits photosynthesis, is
a nonselective herbicide with contact activity,
absorbed by roots and foliage, used post-emer-
gence to control many annual, biennial, and
perennial weeds in alfalfa, pineapples, sugar
cane, in plantations of certain coniferous species,
and on noncrop areas.
Formulation. Wettable granules, suspension
concentrate, tablets.
Trade Names. Velpar, Velpar Weed Killer,
Pronone.
Hexazinone decays with half-lives of 105, 56,
and 56 d in soil, photolytically, and hydrolyti-
cally, respectively.
Metamitron [41394-05-2], 4-amino-4,5-
dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one,
C10H10N4O, Mr 202.21, mp 166.9
C, log Kow
0.85, r 1.35 g/mL, vapor pressure 0.744 mPa, is a
yellowish crystalline solid which is moderately
soluble in water and xylene, and soluble in di-
chloromethane, methanol, ethanol, chloroform,
ethyl acetate, and toluene [1, 2, 360].
Metamitron is produced by reaction of N0 -
acetylbenzylhydrazone with hydroxylamine in
pyridine containing potassium hydroxide [361].
Metamitron, a photosynthesis electron-trans-
port inhibitor, is a selective, systemic herbicide,
absorbed by roots and translocated, used pre-
drilling-incorporated and pre- and post-emer-
gence for the control of grasses and broad-leaved
weeds in sugar, fodder beets, etc.
Formulation. Wettable powder.
Trade Names. Goltix, Tornado, Goldbeet,
Marquise, Skator.
Metamitron decays with half-lives of 30, 0.02,
480, and 11 d in soil, photolytically, hydrolyti-
cally, and in water-sediment, respectively.
Metribuzin [21087-64-9], 4-amino-6-tert-
butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-
one, C8H14N4OS, Mr 214.29 mp 125126.3
C,
log Kow 1.65, r 1.26 g/mL, pKa 13.0, vapor
Vol. 39
pressure 0.121 mPa, consists of colorless crys-
tals which are moderately soluble in water and
hexane, and readily soluble in dimethylforma-
mide, methanol, acetone, xylene, and ethyl ace-
tate [13, 362].
Metribuzin is produced by reaction of 4-ami-
no-5-oxo-3-thioxo-6-tert-butyl-2,3,4,5-tetrahy-
dro-1,2,4-triazine with methyl iodide in the pres-
ence of methoxide [363].
Metribuzin, a photosynthesis electron-transport
inhibitor, is a selective, systemic herbicide with
contact and residual activities used pre- and post-
emergence to control many grasses and broad-
leaved weeds in soya beans, potatoes, tomatoes,
sugar cane, asparagus, maize, and cereals.
Formulation. Wettable powder, water-dis-
persible powder, suspension concentrate.
Trade Names. Sencorex, Lexone 2,Artist,
Shotput.
Metribuzin decays with half-lives of 11.5, 0.2,
and 50 d in soil, photolytically, and in water-
sediment. It is stable towards hydrolysis.
1.17. Amides
Allidochlor [93-71-0], N,N-diallyl-2-chlor-
oacetamide, C8H12ClNO, Mr 173.64, mp 25
C,
bp 115117
C, log Kow 1.83, r 1.04 g/ml, pKa
4.1, vapor pressure 0.0108 mPa, is an oily amber-
colored liquid which is slightly soluble in water,
and soluble in ethanol, hexane, and xylene [2,
364].
Allidochlor can be prepared by reaction of
chloroacetyl chloride with diallylamine [365].
Allidochlor is used pre- and post-emergence
to control annual grasses and certain broad-
leaved weeds in many crops. It inhibits cell
division.
Formulation. Emulsifiable concentrate,
granules.
Vol. 39
Trade Name. Randox.
Beflubutamid [113614-08-7], (RS)-N-ben-
zyl-2-(a,a,a,4-tetrafluoro-m-tolyloxy)butyra-
mide, C18H17F4NO2, Mr 355.33, mp 75
C, log
Kow 4.28, r 1.33 g/mL, vapor pressure
0.011 mPa, is a colorless powder which is spar-
ingly soluble in water, moderately soluble in n-
heptane, and soluble in ethyl acetate, methanol,
xylene, dichloromethane, and acetone [2, 366].
Beflubutamid can be prepared by reaction of
3-(trifluoromethyl)-4-fluorophenol with 2-bro-
mobutyric acid, followed by treatment with sul-
fonyl chloride and benzylamine [258].
Beflubutamid is used post-emergence to con-
trol broadleaf weeds in wheat, barley, rye, triti-
cale. It inhibits phytoene desaturase.
Formulation. Water-dispersible granules.
Trade Names. Herbaflex, UBH-820, UR
50601.
Beflubutamid decays with half-lives of 5.4,
48, and 57 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
Bromobutide [74712-19-0], (RS)-2-bro-
mo-3,3-dimethyl-N-(1-methyl-1-phenylethyl)
butyramide, C15H22BrNO, Mr 312.25, mp
180
C, log Kow 3.48, vapor pressure 74 mPa,
is a colorless solid which is sparingly soluble in
water [2].
Bromobutide can be made by reaction of a,a-
dimethylbenzylamine with bromo-tert-butylace-
tyl chloride in the presence of a base [112].
Bromobutide is used pre- and post-emergence
to control annual and perennial weeds in rice and
various other crops. It inhibits germination of
Weed Control, 2. Individual Herbicides 273
weeds by inhibition of 4-hydroxyphenylpyruvate
dioxygenase.
Formulation. Granules.
Trade Name. Sumiherb.
Dimethenamid [87674-68-8], (R,S)-2-
chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-meth-
oxy-1-methylethyl)acetamide, C12H18ClNO2S,
Mr 275.79, bp 127
C (26.7 Pa), log Kow 2.2, r
1.2 g/mL, vapor pressure 0.35 mPa, is a yellow-
brown viscous liquid which is fairly soluble in
water, and readily soluble in heptane, ethanol,
acetone, toluene, ethyl acetate, and diethyl ether
[1, 2, 367].
Dimethenamid is produced by reaction of 2,4-
dimethyl-3-aminothiene with 2-chloro-3-meth-
oxypropane, followed by treatment with chlor-
oacetyl chloride [368].
Dimethenamid is used pre-emergence for the
control of annual grasses and many broad-leaved
weeds in maize, soya beans, and other crops. It
inhibits cell division, and is only slightly
translocated.
Formulation. Emulsifiable concentrate.
Trade Name. Frontier.
Dimethenamid decays with half-lives of 13
and 17 d in soil and hydrolytically, respectively.
Dimethenamid-P [163515-14-8], (S)-2-
chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-meth-
oxy-1-methylethyl)acetamide, C12H18ClNO2S,
Mr 275.8, bp >280
C, log Kow 1.89, r 1.2 g/
mL, vapor pressure 2.5 mPa, is a yellow-brown
viscous liquid which is moderately soluble in
water and hexane, and soluble in tetrahydrofuran,
acetone, dichloromethane, and dimethylforma-
mide [1, 2, 369].
Synthesis, see parent compound dimethen-
amid.
Dimethenamid-P is a selective herbicide used
as an isomermixture.
274 Weed Control, 2. Individual Herbicides
Formulation. Emulsifiable concentrate.
Trade Names. Elk, Shadow, Springbok.
Dimethenamid-P decays with half-lives of 11,
14, and 28 d in soil, photolytically, and in water-
sediment. It is stable towards hydrolysis.
Diphenamid [957-51-7], N,N-dimethyldi-
phenylacetamide, C16H17NO, Mr 239.31, mp
134135
C, log Kow 2.17, r 1.17 g/mL, vapor
pressure 0.00304 mPa, is a colorless solid
which is moderately soluble in water, xylene,
and dimethylformamide, and soluble in acetone
[13].
Diphenamid is prepared by reaction of diphe-
nyl acetyl chloride with dimethylamine in the
presence of a base [370].
Diphenamid is a selective, systemic herbi-
cide, absorbed by roots, used pre-emergence to
control annual broad-leaved weeds and annual
grasses in a number of crops (e.g., vegetables,
fruit trees)
Formulation. Wettable powder, granules.
Trade Names. Enide, Dymid, Diherbid.
Diphenamid decays in soil with a half-life of
30 d.
Fentrazamide [158237-07-1], 4-(2-chloro-
phenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-
1H-tetrazole-1-carboxamide, C16H20ClN5O2, Mr
349.82, mp 79
C, log Kow 3.60, r 1.30 g/ml, vapor
pressure 0.05 mPa, is a colorless crystalline
solid which is sparingly soluble in water, mod-
erately soluble in n-heptane and isopropyl alco-
hol, and soluble in xylene and dichloromethane
[2].
Fentrazamide can be synthesized by reaction
of o-chloroaniline with phosgene to give 2-chlor-
ophenyl isocyanate, which is further treated with
sodium azide and aluminum trichloride in di-
methylformamide to give 1-(2-chlorophenyl)-5-
(4H)-tetrazolinone, reaction of which with N-
Vol. 39
cyclohexyl-N-ethylcarbamoyl chloride in the
presence of dimethylaminopyridine as catalyst
to yield the desired product [54].
Fentrazamide is a selective herbicide used pre-
and post-emergence to control annual sedges
mainly in transplanted rice. It inhibits cell
division.
Formulation. Granules.
Trade Name. Lecs.
Fentrazamide decays with a half-life of 20 d
photolytically. It is stable towards hydrolysis.
Napropamide [15299-99-7], (RS)-N,N-
diethyl-2-(1-naphthyloxy)propionamide,
C17H21NO2, Mr 271.36, mp 76
C, bp 316.7
C,
log Kow 3.36, r 1.18 g/mL, vapor pressure
0.022 mPa, is a colorless to brown solid which
is sparingly soluble in water, moderately soluble
in n-heptane, and soluble in acetone, ethyl ace-
tate, and dichloromethane [13, 5, 371].
Napropamide can be made by reaction of 1-
naphthol with N,N-diethylbromopropionate in
methanol in the presence of sodium methoxide
[372].
Napropamide is a selective, systemic herbi-
cide, absorbed by roots and translocated, used to
control a number of annual grasses and broad-
leaved weeds in a range of crops. It inhibits root
cell elongation.
Formulation. Suspension concentrate,
emulsifiable concentrate, wettable powder,
granules.
Trade Names. Devrinol, Waylay, R-7165.
Napropamide decays in soil with a half-life of
34217 d.
Naptalam [132-66-1], N-1-naphthylphtha-
lamic acid, C18H13NO3, Mr 291.31, mp 185
190
C, log Kow 0.004, r 1.36 g/mL, pKa 4.6,
vapor pressure 0.133 mPa, is a purple crystalline
solid with an unpleasant odor which is insoluble
in hexane, slightly soluble in water, carbon tet-
rachloride, and xylene, moderately soluble in
acetone, and soluble in methanol and dimethyl-
formamide [13, 373].
Vol. 39
Naptalam can be made by interaction of
phthalic anhydride with 1-naphthylamine in ben-
zene at room temperature [3].
Naptalam is a selective herbicide, absorbed by
roots and to a lesser extent by foliage, used pre-
and post-emergence to control certain dicotyle-
donous weeds in soybeans, cucurbits, and
groundnuts. It inhibits auxin transport.
Formulation. Emulsifiable concentrate, wet-
table powder, granules.
Trade Names. Alanap-3, Alanap Plus, Naptro.
Naptalam decays with half-lives of 14, 7.5,
and 2.9 d in soil, photolytically, and hydrolyti-
cally, respectively.
Pethoxamid [106700-29-2], 2-chloro-N-
(2-ethoxyethyl)-N-(2-methyl-1-phenylprop-1-
enyl)acetamide, C16H22ClNO2, Mr 295.81, mp
37.5
C, log Kow 2.96, r 1.19 g/mL, vapor pres-
sure 0.34 mPa, is an off-white crystalline solid
which is slightly soluble in water, and soluble in
n-heptane, n-hexane, methanol, and ethyl acetate
[2, 374].
Pethoxamid is a systemic herbicide, absorbed
by roots and young shoots, used to control grasses
and broad-leaved weeds in many vegetables and
other crops.
Formulation. Emulsifiable concentrate.
Trade Names. Successor 600, Successor T.
Pethoxamid decays with half-lives of 6, 14
and 7.6 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
Propyzamide [23950-58-5], 3,5-dichloro-
N-(1,1-dimethylprop-2-ynyl)benzamide,
C12H11Cl2NO, Mr 256.13, mp 155156
C, log
K ow 3.3, r 1.33 g/mL, vapor pressure
0.0267 mPa, is a beige to colorless powder which
Weed Control, 2. Individual Herbicides 275
is sparingly soluble in water and hexane, moder-
ately soluble in toluene, and soluble in acetone,
methanol, and isopropyl alcohol [13, 375].
Propyzamide can be prepared by the Schot-
tenBauman reaction of 3,5-dichlorobenzyl
chloride with 3-amino-3-methylbutyne [3].
Propyzamide is a selective, systemic herbi-
cide, absorbed by roots and translocated, used to
control many annual and perennial grasses and
broad-leaved weeds in many crops. It inhibits
photosystem II.
Formulation. Wettable powder, granules,
suspension concentrate.
Trade Names. Bulwark, Kerb Menace.
Propyzamide decays with half-lives of 47, 41
and 94 d in soil, photolytically, and in water-
sediment. It is stable towards hydrolysis.
Tebutam (Butam) [35256-85-0], N-ben-
zyl-N-isopropylpivalamide, C15H23NO, Mr
233.35, bp 95
C, log Kow 3, r 0.98 g/mL, vapor
pressure 89 mPa, is a light brown liquid which is
slightly soluble in water, moderately soluble in
acetone, and soluble in hexane, methanol, and
toluene [2].
Tebutam can be prepared by reaction of N-
benzyl-N-isopropylamine with pivalyl chloride
[112].
Formulation. Water-dispersible granules,
wettable powder.
Trade Names. Comodor, Traton, Colzor.
Tebutam decays in soil with a half-life of 60 d.
It is stable towards photolytic and hydrolytic
actions.
1.18. Anilides
Flamprop [58667-63-3], N-benzoyl-N-(3-
chloro-4-fluorophenyl)-DL-alanine,
C16H13ClFNO3, Mr 321.73, mp 85
C, log Kow
276 Weed Control, 2. Individual Herbicides
2.9, pKa 3.7, vapor pressure 0.239 mPa, is a
colorless crystalline solid which sparingly solu-
ble in water, moderately soluble in hexane, and
soluble in acetone, ethanol, and xylene [2];
Flamprop-M-isopropyl [63782-90-1], isopro-
pyl-N-benzoyl-N-(3-chloro-4-fluorophenyl)-D-
alanine, C19H19ClFNO3, Mr 363.81, mp 73.5
C,
log Kow 3.9, r 1.32 g/L, vapor pressure
0.085 mPa [1, 2].
Flamprop-M-isopropyl can be synthesized
by reaction of propionic acid with chlorine to
give chloropropionic acid which is further trea-
ted with isopropyl alcohol followed by 3-
chloro-4-fluoroaniline and benzoyl chloride
[112].
Flamprop is a selective herbicide, translo-
cated rapidly, used post-emergence to control
wild oat and triticate. It inhibits cell elongation.
Formulation. Granules, water-dispersible
granules.
Trade Names. Barnon, Conado, Suffix,
Matavan.
Flamprop-M-isopropyl decays in soil with a
half-life of 55 d.
Flufenacet (formerly fluthiamid)
[142459-58-3], 40 -fluoro-N-isopropyl-2-[5-(tri-
fluoromethyl)-1,3,4-thiadizol-2-yloxy]acetani-
lide, C14H13F4N3O2S, Mr 363.33, mp 78
C, log
Kow 3.2, r 1.45 g/mL, vapor pressure 0.09 mPa,
is a colorless to tan solid which is sparingly
soluble in water, moderately soluble in hexane,
and soluble in acetone, toluene, and dichloro-
methane [2, 3, 376, 377].
Vol. 39
Flufenacet can be made by reaction of equiv-
alent quantities of 2-methylsulfonyl-5-trifluoro-
methyl-1,3,4-thiadiazole with 2-hydroxy-[N-(4-
fluorophenyl)-N-isopropyl] acetamide in the
presence of sodium hydroxide in acetone at
0
5
C. [258].
Flufenacet is a selective herbicide with meri-
stematic activity applied to soil surface or incor-
porated pre-emergence in field corn, corn grown
for silage or soybean to control certain annual
grasses and broad-leaved weeds. It inhibits cell
division.
Formulation. Dry flowable.
Trade Names: Artist, Cadu Star, Firebird,
Shooter, Regatta.
Flufenacet decays with half-lives of 40 and
81 d in soil and water-sediment, respectively. It
is stable towards photolytic and hydrolytic
actions.
Mefenacet [73250-68-7], 2-(1,3-benzothia-
zol-2-yloxy)-N-methylacetanilide, C16H14N2O2S,
Mr 298.36, mp 134.8
C, log Kow 3.23, r 1.32 g/
mL, vapor pressure 0.64 mPa, consists of colorless
crystals which are sparingly soluble in water,
slightly soluble in hexane, moderately soluble in
toluene, and isopropyl alcohol, and readily soluble
in dichloromethane [1, 2].
Mefenacet can be prepared by reaction of 2-
chlorobenzthiazole with N-methylbenzene hy-
droxyacetamide [378].
Mefenacet is a selective herbicide which in-
hibits cell growth and cell division, used pre-and
post-emergence mainly in transplanted rice.
Formulation. Granules.
Trade Names. Act Nihon, Hinochloa, Ran-
cho, Zark.
Mefenacet decays in soil with a half-life of
35 d. It is stable towards hydrolysis.
Mefluidide [53780-34-0], 50 -(1,1,1-tifluor-
omethanesulfonamido)acet-20 ,40 -xylidide,
C11H13F3N2O3S, Mr 310.29, mp 183185
C,
log Kow 2.08, r 1.46 g/mL, pKa 4.6, vapor
pressure 10 Pa, is a colorless crystalline solid
which sparingly soluble in water, xylene, and
benzene, moderately soluble in n-octanol, and
Vol. 39
soluble in ethyl acetate and acetone [1, 2, 379].
Mefluidide can be synthesized by reaction of
2,4-dimethyl-5-nitroaniline with acetyl chloride,
reduction of the nitro group, and treatment of the
resulting product with trifluoromethylsulfonyl
chloride [258].
Mefluidide is a plant growth regulator, ab-
sorbed by foliage, used post-emergence to con-
trol the growth of ornamental and nonornamental
woody plants, ground cover, trees, turf grasses,
grass, and broad-leaved weeds.
Formulation. Suspension concentrate, gran-
ules, ready-to-use liquid.
Trade Names. Embark 2S, Embark TO.
Mefluidide decays in soil with a half-life of
7 d.
Perfluidone [37924-13-3], 1,1,1-trifluoro-
20 -methyl-40 -(phenylsulfonyl)methanesulfona-
nilide, C14H12F3NO4S2, Mr 379.37, mp 143
145
C, pKa 2.5, vapor pressure 1.23 mPa, is a
colorless crystalline solid which is soluble in
water, acetone, and dichloromethane, and mod-
erately soluble in benzene and aromatic and
chlorinated hydrocarbons [2, 380].
Perfluidone can be prepared by reaction of 3-
methyl-4-nitroaniline with sodium nitrite fol-
lowed by treatment with thiophenol and trifluor-
omethanesulfonyl chloride, and finally with hy-
droperoxide [112].
Perfluidone is used pre-emergence to control
nutsedge species, certain grasses and broad-
leaved weeds in flue-cured tobacco.
Formulation. Wettable powder.
Trade Name. Destum.
Weed Control, 2. Individual Herbicides 277
Perfluidone decays with a half-life of 30 d.
Propanil [709-98-8], 30 ,40 -dichloropropio-
nanilide, C9H9Cl2NO, Mr 218.08, mp 9195
C,
bp 351
C, log Kow 2.29, r 1.41 g/mL, vapor
pressure 0.02 mPa, is a brown crystalline solid
which is sparingly soluble in water and hexane,
and soluble in acetone, ethanol, benzene, and
cyclohexanone [2, 3, 5, 381, 382].
Propanil can be prepared by reaction of 3,4-
dichloroaniline with propionic acid in the pres-
ence of thionyl chloride [3].
Propanil is a selective herbicide with contact
action used post-emergence to control numerous
grasses and broad-leaved weeds in rice, potato
fields, and wheat. Its use is restricted to warm
climatic conditions. It is a photosynthesis inhibitor.
Formulation. Emulsifiable concentrate, ul-
tralow-volume, dry flowable, water-dispersible
granules.
Trade Names. Stampede, Herbax, Montrose
propanil.
Propanil decays with half-lives with 2, 0.5,
and 365 d in soil, photolytically, and hydrolyti-
cally, respectively.
Pyrimisulfan [221205-90-9], (RS)-20 -[(4,6-
dimethoxypyrimidin-2-yl)(hydroxy)methyl]-1,1-
difluoro-60 (methoxymethyl)methanesulfonanilide,
C16H19F2N3O6S, Mr 419.40, mp 98.8
C, log Kow
2.15, r 1.48 g/mL, vapor pressure 21 nPa, is a
colorless powder which is practically insoluble in
water [2].
Pyrimisulfan can be made by reaction of 2-
[(4,6-dimethoxypyrimidin-2yl)(hydroxyl)meth-
yl]-6-methoxymethylaniline with difluoro-
methylsulfonyl chloride [258].
Pyrimisulfan is used to control perennial
weeds in rice. It is an acetolactate synthase
inhibitor.
Formulation. Granules.
278 Weed Control, 2. Individual Herbicides
Trade Names. KIH-5996, KUH-021.
Pyrimisulfan decays wth half-lives of 38
and 45 d photolytically and hydrolytically,
respectively.
1.19. Benzoic Acids
Bispyribac-sodium [125401-92-5], sodium
2,6-bis(4,6-dimethoxypyrimidin-2-yloxy)ben-
zoate, C19H17N4NaO8, Mr 452.4, mp 223
224
C, log Kow 1.03, r 1.47 g/mL, pKa
3.35, vapor pressure 5.5 nPa, is a colorless pow-
der which is sparingly soluble in ethyl acetate, n-
hexane, and acetone, and readily soluble in water
and methanol [1, 2, 5].
Bispyribac-sodium is produced by reaction of
2,6-dihydroxybenzoic acid with 2-chloro-4,6-di-
methoxypyrimidine [383].
Bispyribac-sodium, which inhibits acetolac-
tate synthase, is a selective, systemic post-emer-
gence herbicide, absorbed by foliage and roots,
used to control a range of weeds in directly
seeded rice.
Formulation. Suspension concentrate.
Trade Names. Nominee, Grass-short, Short-
keep, Adora.
Bispyribac-sodium decays with half-lives of
13, 42, and 35 d in soil, photolytically, and in
water-sediment, respectively. It is stable towards
hydrolysis.
Chloramben [133-90-4], 3-amino-2,5,di-
chlorobenzoic acid, C7H5Cl2NO2, Mr 206.03, mp
200
C, log Kow 1.91, pKa 3.4, vapor pressure
0.93 Pa, is a colorless crystalline solid which is
sparingly soluble in water, benzene, and chloro-
form, and soluble in ethanol and acetone [13, 5].
Chloramben can be synthesized by chlorina-
tion of benzoic acid followed by nitration and
reduction of the nitro group to amino [3].
Vol. 39
Chloramben is a selective, soil applied herbi-
cide used pre-emergence to control grasses and
broad-leaved weeds on soybeans, dry beans,
Lima beans, asparagus, peanuts, cucumber. It
inhibits seedling root development.
Formulation. Granules, aqueous solution.
Trade Names. Aiben, Amoben, ACP-M-728.
Chloramben decays with half-lives of 14 and
0.25 d in soil and photolytically, respectively.
Chlorthal-dimethyl [1861-32-1], dimethyl
tetrachloroterephthalate, C10H6Cl4O4, Mr
331.96, mp 156
C, log Kow 4.40, r 1.56 g/mL,
vapor pressure 0.33 mPa, is a colorless crystal-
line solid which is sparingly soluble in water,
moderately soluble in chloroform and xylene,
and soluble in benzene, toluene, and acetone
[13, 5, 384].
Chlorthal-dimethyl can be made by esterifi-
cation of tetrachloroterephthalic acid with meth-
anol [3].
Chlorthal-dimethyl is a selective, nonsystem-
ic herbicide used to control hairy and smooth
crabgrass, witchgrass, green and yellow foxtails
on turf, ornamentals, strawberries, cotton, soy-
beans, etc.
Formulation. Wettable powder, granules,
suspension concentrate.
Trade Names. Dachtal, Fatal, Rid.
Chlorthal-dimethyl decays with half-lives of
33 and more than one- week in soil and photo-
lytically, respectively.
Dicamba [1918-00-9], 3,6-dichloro-o-ani-
sic acid, C8H6Cl2O3, (sodium salt: [10007-85-
9]). Mr 221.04, mp 114116
C, log Kow 2.21, r
1.484 g/mL, pKa 1.87, vapor pressure 4.5 mPa,
consists of colorless crystals which are moder-
ately soluble in hexane, and soluble in water,
ethanol, cyclohexanone, acetone, dichloro-
methane, and toluene [1, 2, 385, 386].
Vol. 39
Dicamba is produced by hydrolysis of 1,2,4-
trichlorobenzene with sodium hydroxide, fol-
lowed by carboxylation, esterification with meth-
anol, methylation of the hydroxyl group, and
hydrolysis of the ester to the acid [387].
Dicamba is a selective systemic herbicide,
with auxin-like growth-regulator activity, ab-
sorbed by leaves and translocated, used to control
annual and perennial broad-leaved weeds and
brush species in cereals, maize, sugar cane, etc.,
and on turf, pastures, rangeland, and nonc-
ropland.
Formulation. Suspension concentrate,
granules.
Trade Names. Banvel, Banvel SGF, Marks-
man, Foundation, Prompt, Relay P.
Dicamba decays with half-lives of 8, 50.3, and
41 d in soil, photolytically, and in water-sedi-
ment, respectively. It is stable towards hydrolysis.
Pyriminobac-methyl [136191-64-5], meth-
yl (EZ)-2-(4,6-dimethoxypyrimidin-2-yloxy)-6-
(1-methoxyiminoethyl)benzoate, C17H19N3O6,
Mr 361.35, log Kow 2.31, r 1.33 g/mL, vapor
pressure 0.031 mPa, is a colorless powder which
sparingly soluble in water and n-hexane, moder-
ately soluble in methanol, and soluble in ethyl
acetate and acetone [2, 388].
Pyriminobac-methyl can, in brief, be prepared
by reaction of 2-hydroxy-6-methoxyiminoethyl-
benzoic acid with 2-chloro-4,6-dimethoxypyri-
midine [388].
Pyriminobac-methyl is a selective, systemic
herbicide, absorbed by foliage, used to control
various grasses and broad-leaved weeds. It in-
hibits the biosynthesis of branched-chain amino
acids.
Formulation. Emulsifiable concentrate,
granules.
Trade Name. Patful.
Pyriminobac-methyl decays photolytically
with a half-life of 205 d.
Weed Control, 2. Individual Herbicides 279
Pyrithiobac-sodium [123343-16-8], sodi-
um 2-chloro-6-(4,6-dimethoxypyrimidin-2-ylthio)
benzoate, C13H10ClN2NaO4S, Mr 348.74, mp
233.8234.2
C, log Kow 0.84, r 1.61 g/mL, pKa
2.34, vapor pressure 4.80 nPa, is an off-white to
colorless solid which is sparingly soluble in ace-
tone, n-hexane, and ethyl acetate, and readily
soluble in water and methanol [13].
Pyrithiobac-sodium is produced by diazotiza-
tion of 2-amino-6-chlorobenzoic acid ethyl ester,
followed by treatment with 4,6-dimethoxy-2-
mercaptopyrimidine, and hydrolysis of the ester
to the acid [389].
Pyrithiobac-sodium, which inhibits acetolac-
tate synthase, is a selective herbicide used pre-
and post-emergence for the control of a wide
range of broad-leaved weeds in cotton.
Formulation. Technical, wettable powder.
Trade Name. Staple.
Pyrithiobac-sodium decays with half-lives of
60 and 13 d in soil and photolytically, respec-
tively. It is stable towards hydrolysis.
1.20. Quinolinecarboxylic Acids
Quinclorac [84087-01-4], 3,7-dichloroqui-
noline-8-carboxylic acid, C10H5Cl2NO2, Mr
242.06, mp 274
C, log Kow 1.15, r 1.75 g/
mL, pKa 4.34, vapor pressure 37.2 mPa, is a
colorless crystalline solid which is insoluble in
methanol and xylene, sparingly soluble in water,
and moderately soluble in acetone [2, 390].
Quinclorac is absorbed by foliage and has
auxin-like activity. It is mainly used to control
crabgrass.
Formulation. Dry flowable, water-dispers-
ible granules, wettable powder.
Trade Name. Facet, Fas-Nox, BAS-514-H.
Quinclorac decays in soil with a half-life of
540 d. It is stable towards hydrolysis.
280 Weed Control, 2. Individual Herbicides
Quinmerac [90717-03-6], 7-chloro-3-
methylquinoline-8-carboxylic acid, C11H8ClNO2,
Mr 221.6, mp 253
C, log Kow 0.41, r 1.49 g/mL,
pKa 4.32, vapor pressure 0.1 nPa, is a colorless
crystalline solid which is slightly soluble in tolu-
ene, moderately soluble in methanol, acetone, and
dichloromethane, and soluble in water [2].
Quinmerac is a synthetic auxin which is ab-
sorbed by roots.
Formulation. Suspension concentrate.
Trade Names. Oryx, Katamaran, Butison
Top, Rebell.
Quinmerac decays with half-lives of 30, 131,
and 180 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
1.21. Benzoylcyclohexanediones
Mesotrione [104206-82-8], 2-(4-mesyl-2-ni-
trobenzoyl)cyclohexane-1,3-dione, C14H13NO7S,
Mr 339.32, mp 165
C, r 1.49 g/mL, log Kow
1.49, pKa 3.12, vapor pressure 42.7 nPa, is a beige
to tan colored liquid or opaque solid with a faint
pleasant odor which is moderately soluble in water,
xylene, toluene, soluble in acetone, ethyl acetate [2,
3, 391].
Mesotrione is prepared by reaction of 3-
methylmercaptonitrobenzene with acetyl chlo-
ride in the presence of aluminum trichloride
yielding the corresponding ketone, which is oxi-
dized with sodium oxychloride giving the corre-
sponding 4-methylsulfonyl compound, which in
turn is condensed with cyclohexane-1,3-dione to
give the corresponding enol ester. The latter is
rearranged to the desired product with potassium
cyanide in the presence of triethylamine [392].
Mesotrione is a selective, systemic herbicide,
absorbed by roots and translocated, used pre- and
post-emergence to control annual broad-leaved
Vol. 39
weeds in corn, in turf grasses on golf courses and
sod farms. It is used as a replacement for atrazine.
It is an inhibitor of 4-hydroxyphenylpyruvate
dioxygenase.
Formulation. Suspension concentrate.
Trade Names. Calaris, Callisto, Tenacity.
Mesotrione decays with half-lives of 5, 89 and
5 d in soil, photolytically, and in water-sediment,
respectively.
Sulcotrione [99105-77-8], 2-(2-chloro-4-me-
sylbenzoyl)cyclohexane-1,3-dione, C14H13ClO5S,
Mr 328.77, mp 139
C, log Kow 1.7, pKa 3.13,
vaopor pressure 5.0 mPa, is a colorless solid which
is moderately soluble in water, xylene, and n-
octanol, and soluble in dichloromethane and ace-
tone [2, 393, 394].
Sulcotrione is made according to the proce-
dure given above for Mesotrione but with 3-
methylmercaptochlorobenzene as starting mate-
rial [392].
Sulcotrione is mainly absorbed by leaves. It
inhibits 4-hydroxyphenylpyruvate dioxygenase.
Formulation. Suspension concentrate, oil-in-
water emulsion.
Trade Name. Mikado.
Sulcotrione decays with half-lives of 25, 26
and 64 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
Tefuryltrione [473278-76-1], 2-{2-chloro-
4-mesyl-3-[(RS)-tetrahydro-2-furylmethoy-
methyl]benzoyl}cyclohexane-1,3-dione,
C20H23ClO7S, Mr 442.91, mp 111115
C, r
1.42 g/mL, log Kow 1.9, vapor pressure 0.64 nPa
[395].
Tefuryltrione can be prepared according to
above-given procedure for mesotrione using 2-
(3-tetrahydro-2-furanyl)methoxymethyl-3-mer-
captomethylchlorobenzene [396].
Vol. 39
Tefuryltrione is a new herbicide in develop-
ment intended to be used on rice.
Tembotrione [335104-84-2], 2-{2-chloro-4-
mesyl-3-[(2,2,2-trifluoromethoxy)methyl]benzo-
yl}cyclohexane-1,3-dione, C17H16ClF3O6S, Mr
440.82, mp 123
C, log Kow 1.09, r 1.56 g/mL,
pKa 3.18, vapor pressure 11 nPa, is a beige colored
powder which is moderately soluble in water,
ethanol, n-hexane, soluble in toluene, ethyl acetate,
dichloromethane, acetone, dimethyl sulfoxide [2,
397, 398].
Tembotrione can be synthesized according to
the above procedure for mesotrione but using
2-(2,2,2-trofluoromethoxymethyl)-3-mercapto-
methylchlorobenzene [392, 398].
Tembotrione is a selective, broad-spectrum
herbicide used post-emergence to control broad-
leaved grassy weeds in corn.
Formulation. Oil-in-water dispersion.
Trade Name. Laudis.
Tembotrione decays with half-lives of 56 and
108 d photolytically and in water-sediment,
respectively. It is stable towards hydrolysis.
1.22. Benzofurans
Benfuresate [68505-69-1], 2,3-dihydro-
3,3-dimethylbenzofuran-5-yl ethanesulfonate,
C12H16O4S, Mr 256.3, mp 3235
C, bp 241
C,
log Kow 2.41, r 0.96 g/mL vapor pressure
4.5 mPa, is an off-white powder which is spar-
ingly soluble in water, moderately soluble in
cyclohexane, and soluble in dichloromethane,
acetone, and toluene [1, 2].
Benfuresate can be made by reaction of
bromoanisole and methyl allyl aldehyde, and
cyclization of the product thus obtained
followed by demethylation and sulfonation
[399].
Weed Control, 2. Individual Herbicides 281
Benfuresate is used pre-plant in rice to control
broad-leaved weeds and sedges. Benfuresate in-
hibits lipid biosynthesis.
Formulation. Granules, suspension
concentrate.
Trade Name. Aige Fu.
Benfuresate decays with half-lives of 18, 7,
and 31 d in soil, photolytically, and hydrolyti-
cally, respectively.
Ethofumesate [16225-79-6], (RS)-2-eth-
oxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl
methanesulfonate, C13H18O5S, Mr 286.34, mp
7072
C, log Kow 2.7, r 1.3 g/mL, vapor pres-
sure 0.65 mPa, is a colorless crystalline solid
with a mild aromatic odor which is sparingly
soluble in water, moderately soluble in hexane,
and soluble in acetone, dichloromethane, ethyl
acetate, ethanol, methanol, and toluene [13,
400, 401].
Ethofumesate can be prepared by reaction of
2-methylpropionaldehyde and morpholine, fol-
lowed by treatment of the product thus obtained
with p-benzoquinone to give 2,3-dihydro-3,3-
dimethyl-2-morpholinobenzofuran-5-ol, which
is treated with mesyl chloride to give the desired
product [3].
Ethofumesate is a selective, systemic herbi-
cide, absorbed by emerging shoots and roots,
used pre- or post-emergence to control annual
broad-leaved weeds and grasses in beets, green
beans, grass seed crops, onions, peas, spinach,
strawberries, tobacco, etc.
Formulation. Suspension concentrate, emul-
sifiable concentrate, granules.
Trade Names. Betanal Expert, Ethosat 500,
Galahad, Goltix Super, Magnum.
Ethofumesate decays with half-lives of 70, 11,
and 530 d in soil, photolytically, and in water-
sediment, respectively.
1.23. Dicarboximides
Cinidon-ethyl [142891-20-1], ethyl (Z)-2-
chloro-3-[2-chloro-5-(cyclohex-1-ene-1,2-dicar-
boximido)phenyl]acrylate, C19H17Cl2NO4, Mr
282 Weed Control, 2. Individual Herbicides
394.25, mp 112.5
C, bp 360
C, log Kow 4.51, r
1.4 g/mL, vapor pressure 0.01 mPa, is a colorless
crystalline powder which is practically insoluble
in water, moderately soluble in n-heptane and
methanol, and soluble in toluene and acetone [2,
402].
Cinidon-ethyl is a selective herbicide with
contact action used to control grasses and
broad-leaved weeds on several crops. It inhibits
protoporphyrinogen oxidase.
Formulation. Suspension concentrate.
Trade Names. Lotus, Orbit.
Cinidon-ethyl decays with half-lives of 1.3,
2.3, 1.5, and 0.2 d in soil, photolytically, hydro-
lytically, and in water-sediment, respectively.
Flumiclorac-pentyl [87546-18-7], pentyl
[2-chloro-5-(cyclohex-1-ene-1,2-dicarboximi-
do)-4-fluorophenoxy]acetate, C21H23ClFNO5,
Mr 423.86, mp 88.990.1
C, log Kow 4.99, r
1.33 g/mL, vapor pressure 0.01 mPa, is a beige
solid which is sparingly soluble in water, mod-
erately soluble in hexane and n-octanol, and
soluble in methanol, acetone, and acetonitrile
[1, 2].
Flumiclorac-pentyl can be synthesized by
reaction of 2-chloro-4-fluorophenol with pentyl
chloroacetate, followed by nitration and reduc-
tion, and finally condensation with cyclohexene-
1-ene-1,2-dicarboxylic acid [403].
Flumiclorac-pentyl is a herbicide with fast
contact action, absorbed by foliage, used post-
emergence to control a number of weeds in field
corn, soybeans, and noncrop areas. It inhibits
protoporphyrinogen oxidase.
Formulation. Wettable powder, emulsifiable
concentrate.
Vol. 39
Trade Names. Resource, Stellar, Sumivere.
Flumiclorac-pentyl decays with half-lives of
2.5, 0.8, and 0.8 d in soil, photolytically, and
hydrolytically, respectively.
Flumioxazin [103361-09-7], N-(7-fluoro-
3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-ben-
zoxazin-6-yl)cyclohex-1-ene-1,2-dicarboxa-
mide, C19H15FN2O4, Mr 354.33, mp 202.8
C,
log Kow 2.55, r 1.52 g/mL, vapor pressure
3.2 mPa, is a yellow-brown powder which is
sparingly soluble in water and hexane, moder-
ately soluble in methanol, and soluble in ethyl
acetate and acetone [13, 404, 405].
Flumioxazin can be made by reaction of 1-
amino-7-fluoro-4,5-dihydro-4-oxo-3-(2-propy-
nyl)-1,4-benzoxazine with cyclohexene-1-ene-
1,2-dicarcoxylic acid [406].
Flumioxazin is used pre-emergence to control
efficiently a wide range of broad-leaved weeds in
soybeans and peanuts. It induces the accumula-
tion of porphyrins leading to membrane damage.
Formulation. Suspension concentrate, wetta-
ble powder, water-dispersible granules, emulsi-
fiable concentrate.
Trade Names. Valor, Digital, Guillotine,
Sumidpya.
Flumioxazin decays with half-lives of 20, 1, 1,
and 2 d in soil, photolytically, hydrolytically,
and in water-sediment, respectively.
1.24. Dinitrophenols
Dinoseb [88-85-7], (RS)-2-sec-butyl-4,6-
dinitrophenol, C10H12N2O5, Mr 240.22, mp 38
42
C, log Kow 2.29, r 1.35 g/mL, pKa 4.62,
vapor pressure 6.7 mPa, is a reddish brown crys-
talline powder or viscous liquid which is spar-
ingly soluble in water, and soluble in ethanol, n-
heptane, xylene, and toluene [2, 3, 407].
Vol. 39
Dinoseb can be prepared from o-sec-butyl-
phenol, sulfuric acid, and nitric acid [3].
Dinoseb is a selective herbicide with contact
action used to control germinating seeds.
Formulation. Emulsifiable concentrate.
Trade Names. Premerge, BNP 20, Aatox,
Dynamite, Basamite, Caldon.
Dinoseb decays in soil with a half-life of 18 d.
It is stable towards hydrolysis.
Dinoterb [1420-07-1], 2-tert-butyl-4,6-di-
nitrophenol, C10H12N2O5, Mr 240.24, mp
125.5126.5
C, log Kow 3.5, r 1.35 g/mL, vapor
pressure 20 mPa, is a pale yellow solid which is
sparingly soluble in water, soluble in ethyl ace-
tate, cyclohexane, dimethylformamide [13].
Dinoterb can be synthesized by nitration of 2-
tert-butylphenol [3].
Dinoterb is selective, nonsystemic contact
herbicide used post-emergence to control annual
weeds in cereals, lucerne, maize, and pre-emer-
gence in beans and peas. It acts like Dinoseb but
is more selective in cereals and less dependent on
climatic conditions.
Formulation. Emulsifiable concentrate.
Trade Names. Herbogil, Nixone, Tolkan S,
Stirpan Forte.
Dinoterb decays with half-lives of 10, 16, and
94 d in soil, photolytically, and in water-sedi-
ment, respectively.
DNOC [534-52-1], 2-methyl-4,6-dinitro-
phenol, C7H6N2O5, Mr 198.13, mp 86
C, bp
220
C, log Kow 2.13, r 1.58 g/mL, pKa 4.31,
vapor pressure 16 mPa, is a yellow colored crys-
talline product which is sparingly soluble in
water, moderately soluble in hexane and metha-
nol, and soluble in ethyl acetate, acetone, and
dichloromethane [13].
DNOC can be made by sulfonation of o-cresol
followed by controlled nitration [3].
Weed Control, 2. Individual Herbicides 283
DNOC is a contact herbicide used to control
broad-leaved weeds in cereals, also used pre-
harvest for desiccation of potatoes and legumi-
nous seed crops. It is highly phytotoxic.
Formulation. Emulsifiable concentrate, wet-
table powder, flowable.
Trade Names. Ibertox, Trifocide, Sandoline.
DNOC decays in soil with a hlf-life of 253 d;
its half-life for biodegradation is 7 d.
1.25. Aliphatic Compounds
Dalapon-sodium [127-20-8], sodium 2,2-
dichloropropionate, C3H3Cl2NaO2, Mr 164.95,
mp 166.6
C (decomp.), log Kow 0.84, r
1.487 g/mL, pKa 1.79, vapor pressure 0.017 mPa,
is a pale colored powder which is readily soluble
in water, fairly soluble in ethanol and methanol,
and moderately soluble in acetone [13, 5].
Dalapon-sodium is produced by chlorination
of propionic acid followed by transformation into
the sodium salt [408].
Dalapon-sodium is a selective, systemic her-
bicide, absorbed by roots and foliage, used to
control annual and perennial grasses on noncrop-
land and in orchards. It inhibits lipid biosynthesis.
Formulation. Suspension concentrate, emul-
sifiable concentrate.
Trade Names. Dalacide, Diserbo Canali,
Unipon.
Dalapon-sodium is stable towards hydrolytic
action; it decays with a half-life of 30 d in soil.
Flupropanate-sodium [22898-01-7], sodi-
um 2,2,3,3-tetrafluoropropanoate, C3HF4NaO2,
Mr 168.02, mp 165167
C, log Kow 1.0, r
1.45 g/mL, vapor pressure 40 mPa, consists of
colorless crystals which are fairly soluble in
water, and sparingly soluble in nonpolar organic
solvents [1, 2].
Flupropanate-sodium is produced by oxida-
tion of 2,2,3,3-tetrafluoropropanol with chromi-
um trioxide followed by transformation into the
salt [409].
Flupropanate-sodium is a systemic herbicide
with low contact activity, absorbed mainly by roots,
which is used for the control of annual and peren-
nial grasses in pastures and in uncultivated land.
Formulation. Water-soluble liquid.
Trade Names. Frenock, TFP, Taskforce, Fre-
nock, Tetrapion.
284 Weed Control, 2. Individual Herbicides
Flupropanate-sodium is resistant to biodegra-
dation in soil.
Iodomethane [74-88-4], iodomethane,
CH3I, Mr 141.94, mp 66.5
C, bp 42
C, log
Kow 1.6, r 2.8 g/mL, vapor pressure 1661 hPa, is
a colorless liquid with a pungent, ether-like odor
which is fairly soluble in water, and miscible with
alcohols, diethyl ether, and acetone [2, 3, 410].
Iodomethane can be made by reaction of meth-
anol with iodine and red phosphorous, or by reac-
tion of potassium iodide with methyl sulfate [3].
Iodomethane is a soil sterilant used to fumi-
gate soils. It acts by nucleophilic displacement
reaction in various amino acids and peptides.
Formulation. Emulsifiable concentrate.
Trade Name. Midas.
Iodomethane decays photolytically with a
half-life of 11.5 d.
Methyl Bromide [74-83-9], methyl bro-
mide, CH3Br, Mr 94.94, mp 93.6
C, bp
3.56
C, log Kow 0.23, r 1.73 g/mL, vapor pres-
sure 166 kPa, is a colorless, volatile liquid which
is sparingly soluble in water, and miscible with
ethanol, diethyl ether, chloroform, benzene and
carbon tetrachloride [1, 3, 5, 411].
Methyl bromide can be prepared by reaction
of methanol with hydrogen bromide [3].
Methyl bromide is a broad-spectrum fumigant
used on soil and nonfood crops.
Formulation. Pressurized gas.
Trade Names. Brom-o-Gas, Celfume.
1.26. Inorganic Compounds
Ammonium sulfamate [7773-06-0], am-
monium sulfamidate, H6N2O3S, Mr 114.12, mp
131.5
C, bp 160
C, log Kow 2.8, r 1.77 g/mL,
pKa 0.9, vapor pressure 0.1 fPa, is a hygroscopic
colorless crystalline solid which is slightly solu-
ble in ethanol, moderately soluble in glycoland
formamide, and soluble in water and ammonia
[13, 5, 412].
Ammonium sulfamate can be prepared by
neutralization of sulfamic acid with ammonium
hydroxide [3].
Vol. 39
Ammonium sulfamate is a systemic, nonse-
lective herbicide, absorbed by leaves, stems and
freshly cut surfaces and translocated, used to
control most woody plants, herbaceous peren-
nials, broad-leaved weeds, and grasses.
Formulation. Oil-water emulsion granules.
Trade Names. Ammat, Root-out, Amicide.
Ammonium sulfamate decays in soil with a
half-life of 50 d. It is stable towards hydrolysis.
Copper Sulfate (see ! Fungicides Agricul-
tural 2. Individual Fungicides)
Sodium Chlorate [7775-09-9], sodium
chlorate, ClNaO3, Mr 106.44, mp 255
C, log
Kow 2.9, r 2.49 g/mL, pKa 2.49, vapor pressure
5.2 nPa, is a colorless solid which is insoluble
in organic solvents, soluble in water [13, 5,
413].
Sodium chlorate is prepared by electrolysis of
sodium chlorate at elevated temperature [3].
Sodium chlorate is a nonselective, systemic
herbicide with a broad spectrum of activity,
translocated to all parts of the weed, used as a
defoliant in a number of crops and against annual
and perennial grasses and weeds in non-agricul-
tural areas.
Formulation. Water-soluble powder.
Trade Names. Drop-leaf, Fall, Chlorax,
Altacide.
Sodium chlorate decays in soil with a half-life
of 200 d. It is stable towards photolysis and
hydrolysis.
1.27. Oxadiazolones
Methazole [20354-26-1], 2-(3,4-dichloro-
phenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione,
C9H6Cl2N2O3, Mr 261.1, mp 123124
C, log Kow
3.22, r 1.60 g/mL, vapor pressure 133 mPa, is a
colorless solid which is sparingly soluble in water
[2, 3].
Vol. 39
Methazole can be synthesized by reaction of
N-(3,4-dichlorophenyl)hydroxylamine with
methyl isocyanate, followed by cyclization of
1-(3,4-dichlorophenyl)-1-hydroxy-3-methylur-
ea with haloformate [3].
Methazole is a pre- and post-emergence her-
bicide used to control annual broad-leaved weeds
and some grasses in garlic, onions, potatoes,
citrus fruits, and stone fruits. It is preferentially
applied to moist soil.
Formulation. Wettable powder, granules.
Trade Names. Probe, Metazol, Bioxane,
Tumic.
Oxadiargyl [39807-15-3], 5-tert-butyl-3-
[2,4-dichloro-5-(prop-2-ynyloxy)phenyl]-1,3,4-
oxadiazol-2-(3H)-one, C15H14Cl2N2O3, Mr
341.18, mp 131
C, log Kow 3.95, r 1.41 g/mL,
vapor pressure 2.5 mPa, is a beige to colorless
powder which is sparingly soluble in water,
moderately soluble in methanol, and soluble in
acetone, ethyl acetate and toluene [2, 414].
Oxadiargyl can be synthesized by nitration of
2,4-dichlorophenol, reduction of the nitro to an
amino group, diazotization and reduction to the
hydrazine, treatment with trimethyllactic chlo-
ride in the presence of triethylamine, followed by
condensation and cyclization with phosgene, and
finally esterification with propargyl chloride
[415].
Oxadiargyl is a selective herbicide, not ab-
sorbed by plants, used pre- and early post-emer-
gence to control broad-leaved weeds and grasses,
annual sedges in rice, upland crops, perennial
crops. It is an inhibitor of protoporphyrinogen
oxidase.
Formulation. Emulsifiable concentrate, sus-
pension concentrate.
Trade Name. Opalo.
Oxadiargyl decays with half-lives of 25, 1,
and 63 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
Weed Control, 2. Individual Herbicides 285
Oxadiazon [19666-30-9], 5-tert-butyl-
3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxa-
diazol-2-(3H)-one, C15H18Cl2N2O3, Mr 345.23,
mp 88.5
C, bp 282
C, log Kow 5.33, vapor
pressure 0.67 mPa, is a colorless solid which is
sparingly soluble in water, and soluble in ace-
tone, benzene, toluene, ethanol, and carbon tet-
rachloride [13].
Oxadiazon is prepared by reaction of 1,2,4,5-
tetrachlorobenzene with isopropyl alcohol to
yield the corresponding ester, which is further
treated with hydrazine, followed by phosgene [3].
Oxadiazon is a selective herbicide with con-
tact activity used to control gasses and broad-
leaved weeds. It inhibits protoporphyrinogen
oxidase.
Formulation. Emulsifiable concentrate,
granules, flowables, wettable powder.
Trade Names. Ronstar 2G, Ronstar Liquid,
Chipco Ronstar.
Oxadiazon decays with half-lives of 135, 59,
31, and 113 d in soil, photolytically, hydrolyti-
cally, and in water-sediment, respectively.
1.28. Oxazoles
Isoxaben [82558-50-7], N-[3-(1-ethyl-1-
methylpropyl)-1,2-oxazol-5-yl]-2,6-dimethoxy-
benzamide, C18H24N2O4, Mr 332.39, mp
175.3
C, log Kow 3.94, r 0.58 g/mL, pKa
9.78, vapor pressure 0.55 mPa, is a colorless
crystalline solid or waxy powder with a mild
aromatic odor which is practically insoluble in
water and hexane, moderately soluble in xylene,
and soluble in methanol, ethyl acetate, and ace-
tone [13, 416].
286 Weed Control, 2. Individual Herbicides
Isoxaben could be made by condensation of
2,6-dimethoxybenzoyl chloride with 5-amino-3-
(1-ethyl-1-methylpropyl)-1,2-oxazole [417].
Isoxaben is a selective, broad-spectrum her-
bicide used pre-emergence to control annual
broad-leaved weeds in turf, ornamentals, winter
barley, wheat, rye, oats, vines, and around orna-
mental trees and shrubs. It disrupts root and stem
development in germinating seeds.
Formulation. Suspension concentrate, dry
flowable.
Trade Names. Fargo, Axit, Skirmish,
Snapshot.
Isoxaben decays with half-lives of 105, 6, and
17 d in soil, photolytically, and in water-sedi-
ment, respectively. It is stable towards hydrolysis.
Isoxaflutole [141112-29-0], (5-cyclopro-
pyl-1,2-oxazol-4-yl)(a,a,a-trifluoro-2-mesyl-p-
tolyl)methanone, C15H12F3NO4S, Mr 359.32, mp
140
C, log Kow 2.32, r 1.59 g/mL, vapor pres-
sure 1.0 mPa, is an off-white to pale yellow solid
which is sparingly soluble in water, moderately
soluble in methanol and toluene, and soluble in
acetone and ethyl acetate [13, 418, 419].
Isoxaflutole is produced by reaction of 1-(4-
trifluoromethyl-2-methylsulfonylphenyl)-3-cy-
clopropyl-2-ethoxymethylenepropane-1,3-dione
with hydroxylamine [420].
Isoxaflutole, which inhibits p-hydoxyphenyl-
pyruvate dioxygenase, is a systemic herbicide,
absorbed by roots and leaves, used pre-emergence
or pre-planting for the control of a broad spectrum
of grass and broad-leaved weeds in maize.
Formulation. Water-dispersible granules.
Trade Names. Balance, Merlin, Alliance,
Balance Pro.
Isoxaflutole decays with half-lives of 2, 1.7,
0.8, and 0.4 d in soil, photolytically, hydrolyti-
cally, and in water-sediment, respectively.
Pyroxasulfone [447399-55-5], 3-[5-(difluor-
omethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-
4-ylmethylsulfonyl]-4,5-dihydro-5,5-dimethyl-
1,2-oxazole, C12H14F5N3O4S, Mr 391.32 [2].
Vol. 39
Pyroxasulfone is a new herbicide with good
residual activity, intended for use on corn. It is an
acetolactate synthase inhibitor.
Trade Name. KIH 485.
Topramezone [210631-68-8], [3-(4,5-dihy-
dro-1,2-oxazol-3-yl)-4-mesyl-o-tolyl](5-hydroxy-
1-methylpyrazol-4-yl)methanone, C16H17N3O5S,
Mr 363.39, mp 221.6
C, log Kow 1.52, r
1.41 g/mL, pKa 4.06, vapor pressure 0.1 nPa, is
a colorless crystalline solid which is moderately
soluble in water, acetone, toluene, ethyl acetate,
and n-heptane [2, 3, 421].
Topramezone can be prepared by condensa-
tion of 2,6-dinitrotoluene with organic nitrites,
followed by cyclization of the product oxime
with ethylene, reduction of the nitro group in
the resulting 3-isoxazolinylnitrobenzene, reac-
tion with dialkyl disulfide, then bromination and
S-oxidation [3].
Topramezone is a selective, systemic herbi-
cide, rapidly absorbed and translocated, used
post-emergence to control specific broad-leaved
weeds and grasses in field corn, sweet corn, and
popcorn.
Formulation. Suspension concentrate.
Trade Names. BAS 670H, Impact,
Topramezone.
Topramezone decays with half-lives of 310
and 198 d in soil and water-sediment, respective-
ly. It is stable towards photolysis and hydrolysis.
1.29. Pyrazoles
Benzofenap [82692-44-2], 2-[4-(2,4-di-
chloro-m-toluoyl)-1,3-dimethylpyrazol-5-yloxy]-
Vol. 39
40 -methylacetophenone, C22H20Cl2N2O3, Mr
431.31, mp 133.3
C, log Kow 4.69, r 1.088 g/mL,
vapor pressure 0.013 mPa, is a colorless solid
which is sparingly soluble in water, moderately
soluble in n-hexane, and soluble in xylene, acetone,
and chloroform [1, 2].
Benzofenap can be prepared by reaction of
1,3-dimethyl-5-pyrazolone with 2,4-dichloro-3-
methylbenzoyl chloride, followed by treatment
of the product thus obtained with 4-methyl-a-
bromoacetophenone [422].
Benzofenap is a systemic herbicide, absorbed
by roots, mainly used to control broad-leaved
weeds in a number of crops.
Formulation. Suspension concentrate.
Trade Names. Taipan, Yukawide.
Benzofenap decays in soil with a half-life of
38 d.
Fluazolate [174514-07-9], isopropyl 5-[4-
bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-
2-chloro-4-fluorobenzoate, C15H12BrClF4N2O2,
Mr 443.62, mp 80
C, log Kow 5.44, r 1.62 g/mL,
vapor pressure 9.43 mPa, is a colorless crystalline
product which is practically insoluble in water [2].
Fluazolate can be produced by reaction of
trifluoromethylsulfonyl fluoride with N-methyl-
4-bromopyrazole and ethyl 2-chloro-4-fluoro-
phenoxyethylacetate [423].
Fluazolate is a photosynthesis inhibitor used
to control broad-leaved weeds and grasses on
wheat.
Formulation. Granules.
Trade Names. Twinagro, JV 485, MON 48500.
Fluazolate decays in soil with a half-life of
44 d.
Weed Control, 2. Individual Herbicides 287
Pinoxaden [243973-20-8], 8-(2,6-diethyl-
p-tolyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo
[1,2-d][1,4,5]oxadiazepin-9-yl 2,2-dimethylpro-
pionate, C23H32N2O4, Mr 400.51, mp 120
121
C, log Kow 3.2, r 1.1.6 g/mL, vapor pres-
sure 0.46 mPa, is a beige to colorless powder
which is slightly soluble in water, moderately
soluble in hexane, and soluble in acetone, di-
chloromethane, and toluene [2, 424].
Pinoxaden can be produced by condensation
of 2-6-diethyl-4-methylphenylacetic tert-butyl-
anhydride, hydrazine, and diethylene glycol
[425].
Pinoxaden is used post-emergence to control
annual grasses and weeds in some cereal crops.
Formulation. Emulsifiable concentrate.
Trade Names. Axial, Greencropp Helvick.
Pinoxaden decays with half-lives of 0.5, 29.5,
14.9, and 0.27 days in soil, photolytically, hy-
drolytically, and in water-sediment, respectively.
Pyraflufen-ethyl [129630-19-9], ethyl 2-
chloro-5-(4-chloro-5-difluoromethoxy-1-
methylpyrazol-3-yl)-4-fluorophenoxyacetate,
C15H13Cl2F3N2O4, Mr 413.18, mp 126127
C,
log Kow 3.49, r 1.565 g/mL, vapor pressure 4.3
nPa, is a cream-colored crystalline solid which is
practically insoluble in water, sparingly soluble
in n-heptane, and moderately soluble in metha-
nol, and soluble in xylene, acetone, and ethyl
acetate [2, 3, 426].
Pyraflufen-ethyl can be synthesized by reac-
tion of fluorosulfonyldifluoroacetic acid with N-
methyl-4-chloro-5-hydroxypyrazol and ethyl-2-
chloro-4-fluorophenoxy acetic acid [423].
288 Weed Control, 2. Individual Herbicides
Pyraflufen-ethyl is a selective herbicide with
contact activity used to control broad-leaved
weeds and grasses in a range of crops.
Formulation. Suspension concentrate, emul-
sifiable concentrate.
Trade Names. Edict, Octane, Et 2%.
Pyraflufen-ethyl decays with half-lives of 4,
1.4, 13, and 0.1 d in soil, photolytically, hy-
drolytically, and in water-sediment, respec-
tively.
Pyrasulfotole [365400-11-9], (5-hydroxy-
1,3,dimethylpyrazol-4-yl)(a,a,a-trifluoro-2-
mesyl-p-tolyl)methanone, C14H13F3N2O4S, Mr
244.3, mp 201
C, log Kow 1.36, r 1.53 g/mL,
pKa 4.2, vapor pressure 0.27 mPa, is a beige
powder which is sparingly soluble in n-hexane,
moderately soluble in toluene, and soluble in
water, ethanol, acetone, dichloromethane, and
ethyl acetate [2, 3, 427, 428].
Pyrasulfotole can be made by reaction of 2-
chloro-4-trifluoromethylbenzoic acid with so-
dium methylsulfide, followed by treatment
with hydrogen peroxide and sulfonyl chloride,
and finally with 1,3-dimethyl-5-pyrazolone
[428].
Pyrasulfotole is a selective herbicide used
post-emergence to control broad-leaved weeds
in cereal grains (wheat, barley, oats, rye, triti-
cate). It inhibits 4-hydroxyphenylpyruvate
dioxygenase.
Formulation. Suspension concentrate.
Trade Names. Huskie AE 0317309.
Pyrasulfotole decays with half-lives of 55.5
and 365 d in soil and water-sediment, respec-
tively. It is stable towards photolysis and
hydrolysis.
Pyrazolynate (pyrazolate) [58011-68-0],
4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-
yl toluene-4-sulfonate, C19H16Cl2N2O4S, Mr
439. 31, mp 117.5118.5
C, log Kow 3.90, vapor
pressure 0.13 mPa, is a colorless crystalline
product which is practically insoluble in water,
moderately soluble in ethanol, and soluble in
dioxane and ethyl acetate [429, 430].
Vol. 39
Pyrazolynate can be obtained by reaction of
1,3-dimethyl-5-pyrazolone with 2,4-dichloro-
benzoyl chloride in the presence of alkali and
condensation of the product thus obtained with p-
toluenesulfonyl chloride [431].
Pyrazolynate is absorbed by roots and used
pre-or post-transplantation to control annual and
perennial grasses and sedges in paddy rice. It
inhibits chlorophyll biosynthesis.
Formulation. Granules.
Trade Names. SW-751, Methanone, Sanbird.
Pyrazolynate decays with half-lives of 25
hours and 1020 d hydrolytically and in soil,
respectively.
Pyrazoxyfen [71561-11-0], 2-[4-(2,4-di-
chlorobenzoyl)-1,3-dimethylpyrazol-5-yloxy]
acetophenone, C20H16Cl2N2O3, Mr 403.36, mp
111
C, log Kow 3.69, r 1.37 g/mL, vapor pres-
sure 0.048 mPa, is a colorless crystalline solid
which is sparingly soluble in water and hexane,
moderately soluble in ethanol, and soluble in
acetone and benzene [1, 2].
Pyrazoxyfen can be synthesized by reaction
of 1,3-dimethyl-5-pyrazolone with 2,4-di-
chlorobenzoyl chloride in the presence of al-
kali, followed by condensation of the product
thus obtained with a-chloroacetophenonone
[432].
Pyrazoxyfen is a selective, systemic herbi-
cide, absorbed by young stems and roots, used
pre-and post-emergence to control annual and
perennial weeds, mainly in rice crops. It inhibits
chlorophyll biosynthesis.
Formulation. Suspension concentrate,
granules.
Trade Names. Mondaris, Paicer, SL 49.
Pyrazoxyfen decays in soil with a half.life of
10 d.
Vol. 39
1.30. Pyridazines
Pyridate [55512-33-9], O-6-chloro-3-phe-
nylpyridazin-4-yl S-octyl thiocarbonate,
C19H23ClN2O2S, Mr 378.92, mp 27
C, log Kow
0.5, r 1.28 g/mL, vapor pressure 0.998 mPa,
forms colorless crystals which are sparingly sol-
uble in water, and soluble in kerosene, acetone,
ethyl acetate, and xylene [1, 2, 433].
Pyridate is produced by reaction of acetophe-
none with diethyl oxalate, followed by reaction
with hydrazine, phosphorus pentachloride, and
octylmercaptocarboxy chloride [434].
Pyridate, which inhibits photosystem II elec-
tron transport in photosynthesis, is a selective
herbicide used post-emergence to control annual
broad-leaved weeds in maize, sweetcorn, cereals,
rice, and other crops.
Formulation. Wettable powder, emulsifiable
concentrate.
Trade Names. Lentagran, Pirate.
Pyridate decays with half-lives of 5, 1.8, 2.5,
and 1 d in soil, photolytically, hydrolytically,
and in water-sediment, respectively.
1.31. Pyridazinones
Chloridazon [1698-60-8], 5-amino-4-chloro-
2-phenylpyridazin-3(2H)-one, C10H8ClN3O, Mr
221.6, mp 206
C, log Kow 1.19, r 1.51 g/mL, pKa
3.38, vapor pressure 1.0 nPa, is a colorless crystal-
line solid which is slightly soluble in water, dichlor-
omethane, toluene, moderately soluble in ethyl
acetate, benzene, soluble in methanol, acetone
[13, 435].
Chloridazon can be made by reaction of phe-
nylhydrazone and 3,4-dichloro-2,5-dihydro-5-
hydroxyfuran-2-one follow by treatment of the
product thus obtained with ammonia [3].
Weed Control, 2. Individual Herbicides 289
Chloridazon is a selective, systemic herbicide
with residual action used pre-plant and pre- and
early post-emergence to control broad-leaved
weeds in beet crops.
Formulation. Wettable powder, flowable,
dry flowable.
Trade Names. Ashlade, Magnum, Pyramin,
Questar.
Chloridazon decays with half-lives of 31, 40,
and 137 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
Flufenpyr-ethyl [188489-07-8], ethyl 2-
chloro-5-[1,6-dihydro-5-methyl-6-oxo-4-(trifluor-
omethyl)pyridazin-1-yl]-4-fluorophenoxyacetate,
C16H13ClF4N2O4, Mr 408.73, r 1.45 g/mL [2].
Flufenpyr-ethyl can be obtained by reaction of
4-(trifluoromethyl)-5-methyl-6-oxopyridazin
with ethyl 2,5-dichloro-4-fluorophenoxy acetate
[258].
Flufenpyr-ethyl is a new herbicide used on
potatoes, maize, sugarcane, corn, soybean,
wheat. It inhibits protoporphyrinogen oxidase.
Formulation. Water-dispersible granules,
emulsifiable concentrate.
Trade Names. Axiron, S-3153, ET-751, ET-
751 technical.
Norflurazon [27314-13-2], 4-chloro-5-
methylamino-2-(a,a,a-trifluoro-m-tolyl)pyrida-
zin-3-(2H)-one, C12H9ClF3N3O, Mr 303.67, mp
177
C, log Kow 2.45, r 1.45 g/mL, vapor pressure
3.9 mPa, is a grayish to colorless crystalline pow-
der which is insoluble in carbon disulfide, sparing-
ly soluble in water, moderately soluble in xylene,
and soluble in ethanol and acetone [13, 436].
290 Weed Control, 2. Individual Herbicides
Norflurazon can be synthesized by reaction of
4-chloro-5-methylamino-3-oxo-pyrazine with p-
chlorotrifluoromethyltoluene [3].
Norflurozon is a selective herbicide, absorbed
by roots and translocated, used pre-emergence to
control germinating annual broad-leaved weeds,
grasses, and sedges in a number of crops. It
inhibits the biosynthesis of carotenoids.
Formulation. Wettable powder, granules, dry
flowable.
Trade Names. Zorial, Solicam, Evital,
Predict.
Norflurazon decays in soil with a half-life of
90 d. It is stable towards hydrolysis.
1.32. Quaternary Ammonium
Compounds
Difenzoquat-methylsulfate [43222-48-6],
1,2-dimethyl-3,5-diphenylpyrazolium methyl-
sulfate, C18H20N2O4S, Mr 360.43, mp 157
C,
log Kow 0.61, r 0.8 g/mL, pKa 7, vapor pressure
0.01 mPa, is a colorless crystalline solid which is
moderately soluble in acetone, and soluble in
water, methanol, chloroform, and dichloro-
methane [1, 2, 437].
Difenzoquat-methylsulfate can be prepared
by reaction of acetophenone with benzaldehyde,
hydrogen peroxide, hydrazine and dimethyl sul-
fate [422].
Difenzoquat-methylsulfate is a selective her-
bicide, absorbed by foliage, used post-emergence
to control wild oats in alfalfa, wheat, and barley.
It acts by rapid destruction of cell membranes.
Formulation. Suspension concentrate.
Trade Name. Avenge.
Defenzoquat-methylsulfate decays in soil
with a half-life of 90 d. It is stable towards
hydrolysis.
Diquat [2764-72-9], 9,10-dihydro-8a,10a-
diazoniaphenanthrene, C12H12N2, Mr 184.24, mp
(decomp.), log Kow 4.6, r 1.61 g/mL, vapor
pressure 1.0 mPa, is a yellow crystalline solid
Vol. 39
which is slightly soluble in acetone, hexane, and
ethyl acetate, moderately soluble in methanol,
and soluble in water [13, 5].
Diquat can be prepared by reaction of 2,20 -
bipyridine with ethylene dibromide [3].
Diquat is a nonselective, contact herbicide,
absorbed by foliage, with nonresidual activity
used to control broad-leaved weeds, is also used
as a crop desiccant.
Formulation. Suspension concentrate, water-
dispersible granules, ready-to-use liquid.
Trade Names. Reglox, Weedtrine-D, Dei-
quat, Dextrone, Reward.
Diquat decays with half-lives of 1000 and
160 d in soil and water-sediment, respectively.
Paraquat [4685-14-7], 1,10 -dimethyl-4,40 -
bipyridinium, C12H14N2, Mr 186.25, mp 175
180
C (decomp.), log Kow 4.5, r 1.5 g/mL,
vapor pressure 0.01 mPa, is a colorless to pale
yellow crystalline solid which is sparingly solu-
ble in acetone, toluene, and hexane, and soluble
in water and methanol [13, 5].
Paraquat can be prepared by direct quaterni-
zation of 4,40 -bipyridyl with methyl chloride or
dimethyl sulfate in water [3].
Paraquat is a nonselective, nonresidual quick-
acting herbicide on contact used to control broad-
leaved weeds and grasses in a wide range of
agriculture. It possesses also some desiccant
activity. It inhibits photosynthesis.
Formulation. Suspension concentrate,
granules.
Trade Names. Gramoxone, Agriguard para-
quat, Weedol, Toxer.
Paraquat decays in soil with a half-life of
3000 d. It is stable in water-sediment and
towards hydrolysis.
1.33. Miscellaneous Compounds
Acrolein [107-02-8], acrylaldehyde, C3H4O,
Mr 56.1, mp 87
C, bp 52.5
C, log Kow 0.01, r
0.84 g/mL, vapor pressure 290 hPa, is a yellow to
Vol. 39
colorless liquid which is miscible with benzene and
diethyl ether and soluble in water [13, 438441].
Acrolein can be prepared by condensation of
formaldehyde with acetaldehyde [3].
Acrolein is an algicide and aquatic herbicide
with contact action used to clear ditches and
drainage canals. It acts by degradation of cell
structure.
Formulation. Liquid.
Trade Names. Magnacide, Aqualin.
Acrolein decays with half-lives of 17, 4, and
1.5 d in soil, photolytically, and hydrolytically,
respectively.
Aminocyclopyrachlor [858956-08-8], 6-
amino-5-chloro-2-cyclopropylpyrimidine-4-car-
boxylic acid, C8H8ClN3O2, Mr 213.62.
Its use on turf is pending.
Bentazone [25057-89-0], 3-isopropyl-1H-
2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide,
C10H12N2O3S, Mr 240.3, mp 140
C, log Kow
0.46, r 1.41 g/mL, pKa 3.28, vapor pressure
0.17 mPa, is a grayish crystalline solid which is
practically insoluble in n-hexane, sparingly sol-
uble in water, moderately soluble in toluene, and
soluble in acetone, ethanol, chloroform, ethyl
acetate, and methanol [1, 2, 5].
Bentazone can be made by reaction of methy-
lanthralinate with isopropylsulfamoyl chloride
[442].
Bentazone is a selective herbicide with con-
tact action, absorbed by foliage but only slightly
translocated, used post-emergence to control
broad-leaved weeds and sedges in beans, rice,
peanuts, mint, and other crops. It inhibits photo-
system II.
Weed Control, 2. Individual Herbicides 291
Formulation. Suspension concentrate,
granules.
Trade Names. Bendioxide, Basagran, Zone 48.
Bentazone decays with half-lives of 13, 4, and
716 d in soil, photolytically, and in water-sedi-
ment, respectively. It is stable towards hydrolysis.
Benzobicyclon [156963-66-5], 3-(2-chloro-
4-mesylbenzoyl)-2-phenylthiobicyclo[3.2.1]oct-
2-en-4-one, C22H19ClO4S2, Mr 446.97, log Kow
3.1, r 1.45 g/mL, vapor pressure 0.056 mPa, is a
pale yellow crystalline solid which is practically
insoluble in water [2].
Benzobicyclon can be made using norcam-
phor as starting material, which is subjected to
the Mannich reaction followed by BayerVilli-
ger oxidation affording the precursor keto ester
which is then cyclized, and the product thus
obtained is treated with 2-chloro-4-mesylben-
zoyl chloride [443].
Benzobicyclon is a selective herbicide, ab-
sorbed by roots and basal stems, and translocated,
used to control annual and perennial weeds in
rice. It inhibits carotinoid biosynthesis.
Formulation. Liquid, water-dispersible gran-
ules, granules.
Trade Names. Radical Jumbo, Jumbo Sun-
shine, Showace.
Benzobicyclon decays with half-lives of 16.5
and 16.6 h photolytically and hydrolytically,
respectively.
Chlorflurenol-methyl [2536-31-4], methyl
(RS)-2-chloro-9-hydroxyfluorene-9-carboxylate,
C15H11ClO3, Mr 274.71, mp 155
C, log Kow 1.6,
r 1.5 g/mL, vapor pressure 0.13 mPa, is a color-
less crystalline solid which is sparingly soluble in
water, moderately soluble in ethanol and isopro-
pyl alcohol, and soluble in acetone and methanol
[1, 2, 444].
292 Weed Control, 2. Individual Herbicides
Chlorflurenol-methyl is a plant growth regu-
lator, absorbed by leaves and roots, used to
control grasses in roadsides, railways, ditch
banks, and on pickling cucumbers.
Formulation. Emulsifiable concentrate.
Trade Names. Repar, Break-thru, Multiprop,
Maintain A, Morphactin.
Chlorflurenol-methyl decays with half-lives
of 1.5 and 0.4 d in soil and photolytically,
respectively.
Cinmethylin (cycloheptan-ethyl) [87818-
31-3], is a 1:1 mixture of 1RS,2SR,4SR and
1S,2R,4R isomers of 1,4-epoxy-p-menth-2-yl
2-methylbenzyl ether ([87818-61-9]: exo-()
isomer; [87860-60-1]: exo-() isomer),
C18H26O2, Mr 274.44, mp decomp., bp 313
C,
log Kow 3.84, r 1.014 g/mL, vapor pressure
10.1 mPa, is a colorless liquid (if pure) which
is sparingly soluble in water and miscible with
acetone and ethyl acetate [1, 2].
Cinmethylin can be prepared by reaction of
hydroxyl-1-methyl-4-isopropyl-7-oxabicyclo
[2,2,2]heptane with o-methylbenzyl chloride in
the presence of a base [422, 431].
Cinmethylin is a selective, systemic herbi-
cide, absorbed by roots and translocated, used
pre-emergence to control annual grass weeds in
paddy rice, cotton, peanuts and many other
crops.
Formulation. Emulsifiable concentrate,
granules.
Trade Names. Cinch, Argold, WL95481.
Cinmethylin decays half-lives of 50 and 30 d
in soil and hydrolytically, respectively. It is
stable towards photolysis.
Clomazone [81777-89-1], 2-(2-chloroben-
zyl)-4,4-dimethyl-1,2-oxazolidin-3-one,
C12H14ClNO2, Mr 239.7, mp 33.9
C, bp
281.7
C, log Kow 2.54, r 1.19 g/mL, vapor
pressure 19.2 mPa, is a colorless solid which is
slightly soluble in water, moderately soluble in n-
heptane and methanol, and soluble in acetone,
dichloromethane, chloroform, acetonitrile, and
dimethylformamide [1, 2, 5, 445].
Vol. 39
Clomazone can be made by reaction of 3-
chloro-2,2-dimethylpropionyl chloride with hy-
drozylamine hydrochloride, followed by reaction
with o-chlorobenzyl chloride [446].
Clomazone is a selective, broad-spectrum
herbicide, absorbed by roots and shoots, used
pre-plant and pre-emergence to control broad-
leaved weeds and annual grasses in a range of
crops.
Formulation. Capsular suspension.
Trade Names. Centium 36, Command.
Cloamzone decays with half-lives of 83 and
54 d in soil and water-sediment, respectively. It
is stable towards photolysis and hydrolysis.
Endothal [145-73-3], 7-oxabicyclo[2.2.1]
heptane-2,3-dicarboxylic acid, C8H10O5, Mr
186.16, mp 144
C, log Kow 1.91, r 1.43 g/mL,
pKa1 3.4, pKa2 6.7, vapor pressure 20.9 nPa, is a
colorless crystalline solid which is slightly solu-
ble in benzene, moderately soluble in acetone
and dioxane, and soluble in water and methanol
[13, 5, 447].
Endothal is made by reduction of the Diels
Alder condensation product of furan and maleic
anhydride [3].
Endothal is a selective herbicide with contact
activity, absorbed by leaves and roots, used pre-
and post-emergence to control broad-leaved
weeds and annual grasses in sugar beets, spinach,
and turf, algae, and aquatic weeds. It is also used
as a defoliant and desiccant on cotton, alfalfa, and
clover.
Formulation. Granules, suspension concen-
trate, aquatic suspension.
Trade Names. Niagrathal, Hydrothal, Weeds
Killer, Aquathol, Accelerate.
Endothal decays with half-lives of 4-5 and 7 d
in soil and hydrolytically, respectively.
Fluridone [59756-60-4], 1-methyl-3-phe-
nyl-5-(a,a,a-trifluoro-m-tolyl)-4-pyridone,
Vol. 39
C19H14F3NO, Mr 329.32, mp 154.5
C, log Kow
1.87,d 0.36 g/mL, pKa 12.3, vapor pressure
0.013 mPa, is a colorless crystalline product
which is sparingly soluble in water and hexane,
and moderately soluble in ethyl acetate, chloro-
form, and methanol [13, 448, 449].
The synthesis of fluridone is described in
[450].
Fluridone is a selective, systemic herbicide
with a broad spectrum, absorbed mainly by
roots, used in aquatic situations, e.g. freshwater
ponds, lakes, reservoirs, drainage canals, irriga-
tion canals, and rivers. It is effective at very low
doses.
Formulation. Pellets, aquatic suspension.
Trade Names. Avast, Sonar, Brake, Pride.
Fluridone decays with half-lives of 21 and 1 d
in soil and photolytically, respectively. It is stable
towards hydrolysis.
Flurochloridone (Fluorochloridone)
[61213-25-0], a mixture of the enantiomeric pairs
(3RS,4RS;4RS,4SR)-3-chloro-4-chloromethyl-1-
(a,a,a-trifluoro-m-tolyl)-2-pyrrolidone (iso-
mers in the ratio 3:1), C12H10Cl2F3NO, Mr
312.2, mp 40.9
C, log Kow 3.3.6, r 1.19 g/mL,
vapor pressure 0.44 mPa, is a beige-colored
waxy solid which is sparingly soluble in water,
and soluble in acetone, ethyl acetate, and tolu-
ene [1, 2].
Flurochloridone can be made by reaction of 3-
trifluoromethylaniline, acetylacetone, and acry-
lolyl chloride [451].
Flurochloridone is a selective herbicide, ab-
sorbed by roots and stems, used pre-emergence in
a wide range of weeds in umbelliferous crops,
Weed Control, 2. Individual Herbicides 293
cereals, and potatoes. It inhibits carotenoid
biosynthesis.
Formulation. Capsule suspension.
Trade Name. Racer.
Flurochloridone decays with half-lives of 92,
6.5, and 37 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
Flurtamone [96525-23-4], (RS)-5-methy-
lamino-2-phenyl-4-(a,a,a-trifluoro-m-tolyl)fu-
ran-3-(2H)-one, C18H14F3NO2, Mr 333.30, mp
152155
C, log Kow 3.2, r 1.38 g/mL, vapor
pressure 0.45 mPa, is a ivory-colored powder
which is sparingly soluble in water and hexane,
moderately soluble in octanol and toluene, and
soluble in acetone, methanol, ethyl acetate, and
ethanol [1, 2, 452, 453].
Flurtamone is an herbicide used pre-plant
incorporation, pre- or post-emergence to control
broad-leaved and some grass weeds in winter
barley, winter rye, winter wheat, triticale. It
inhibits carotenoid biosynthesis.
Formulation. Spray, suspension concen-
trate.
Trade Names. Baccara, Baccara Forte, Grad-
uate, Ingot.
Flurtamone decays with half-lives of 56, 1,
and 80 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
Fluthiacet-methyl [117337-19-6], methyl
{2-chloro-4-fluoro-5-[(EZ)-5,6,8-tetrahydro-3-oxo-
1H,3H-[1,3,4,]thiadiazolo[3,4-a]pyridazin-1-ylide-
neamino]phenylthio} acetate, C15H15ClFN3O3S2,
Mr 403.9, mp 105.0106.5
C, log Kow 3.77, r
0.43 g/mL, vapor pressure 0.44 mPa, is a colorless
powder which is sparingly soluble in water, moder-
ately soluble in methanol and dichloromethane, and
dissolves well in acetone, acetonitrile, and ethyl
acetate [13, 454].
294 Weed Control, 2. Individual Herbicides
Fluthiacet-methyl is produced by reaction of
1-[(2-fluoro-4-chloro-5-thiomethylacetate)phe-
nylthiocarbamoyl]-2-methoxycarbonylhexahy-
dropyridazine with methanolic potassium hy-
droxide, followed by treatment with trichloro-
methyl chloroformate [455].
Fluthiacet-methyl, which inhibits protopor-
phyrinogen oxidase, is a selective contact herbi-
cide used post-emergence for the control of
broad-leaved weeds in maize and soya beans.
Formulation. Water-soluble bags.
Trade Names. Action, Blizzard, Appeal.
Fluthiacet-methyl decays in soil with a half-
life of 8 d. It is stable towards hydrolysis.
Indanofan [133220-30-1], (R,S)-2-[2-(3-
chlorophenyl)-2,3-epoxypropyl]-2-ethylindan-
1,3-dione, C20H17ClO3, Mr 340.80, mp 60.0
62.5
C, log Kow 3.59, r 1.24 g/mL, vapor pres-
sure 0.028 mPa, is a colorless crystalline solid
which is sparingly soluble in water, moderately
soluble in hexane, and soluble in methanol, ace-
tone, and ethyl acetate [1, 2, 456].
Indanofan is produced by reaction of 2-[2-(3-
chlorophenyl)propen-3-yl]-2-ethyllindan-1,3-
dione with peracetic acid [457].
Indanofan is a selective, systemic herbicide
used for pre-and post-emergence use, for the
control of weeds in transplanted rice. It inhibits
the biosynthesis of very long chain fatty acids.
Formulation. Granules.
Trade Name. Dainaman.
Indanofan decays in soil with a half-life of 2 d.
Oxaziclomefone [153197-14-9], 3-[1-(3,5-
dichlorophenyl)-1-methylethyl]-3,4-dihydro-
6-methyl-5-phenyl-2H-1,3-oxazin-4-one,
C20H19Cl2NO2, Mr 376.28, mp 180
C, log Kow
5.15, is a colorless solid which is sparingly
soluble in water [2].
Vol. 39
Oxaziclomefone can be prepared by reaction
of N-methylenecumylamine and 1,3-dioxin-4-
one [458].
Oxaziclomefone is a novel herbicide with
contact action and some residual activity used
to control cockspur, annual sedges, and other
grasses in paddy fileds. It is a plant growth
inhibitor.
Formulation. Granules, wettable powder,
suspension concentrate.
Trade Names. Homerun, Patful, Thourghbred.
Oxaziclomefone decays in soil with a half-life
of 364 d.
Pentoxazone [110956-75-7], 3-(4-chloro-5-
cyclopentyloxy-2-fluorophenyl)-5-isopropyli-
dene-1,3-oxazolidine-2,4-dione, C17H17ClFNO4,
Mr 353.77, mp 104
C, log Kow 4.66, r 1.42 g/
mL, vapor pressure 0.11 mPa, is a colorless crys-
talline solid which is practically insoluble in
water, moderately soluble in hexane, and soluble
in methanol [2].
Pentoxazone is an herbicide with a long last-
ing effect used to control annual broad-leaved
weeds on barnyards, grasses and monocholia in
paddy fields.
Formulation. Granules, suspension concen-
trate, water-dispersible granules.
Trade Names. Wechser, Top Gun.
Pentocazone decays with half-lives of 29 and
5 d in soil and hydrolytically, respectively
Pyribenzoxim [168088-61-7], benzophe-
none O-[2,6-bis(4,6-dimethoxypyrimidin-2-
yloxy)benzoyl]oxime, C32H27N5O8, Mr 609.59,
mp 128130
C, log Kow 3.04, r 1.3 g/mL, vapor
pressure 7.4 mPa, is a colorless solid which is
Vol. 39
sparingly soluble in water [2].
Pyribenzoxim can be prepared by acetylation
of 2,6-dihydroxybenzoic acid, followed by treat-
ment with thionyl chloride and then with benzo-
phenoxime. The product thus obtained is treated
with 4,6-dimethoxy-2-methylsulfonylpyrimidine
in the presence of potassium carbonate in di-
methylformamide [431].
Pyribenzoxim is a selective, broad-spectrum
herbicide used post-emergence to control grasses
and polygonums in rice, wheat and other crops. It
inhibits acetolactate synthase.
Formulation. Emulsifiable concentrate.
Trade Name. Pyanchor, LGC 40863.
Pyribenzoxim decays in soil with a half-life of
7 d.
Pyriftalid [135186-78-6], (RS)-7-(4,6-di-
methoxypyrimidin-2-ylthio)-3-methyl-2-benzo-
furan-1(3H)-one, C15H14N2O4S, Mr 318.35, mp
163.4
C, log Kow 2.6, r 1.44 g/mL, vapor pres-
sure 22 nPa, is a colorless solid which is sparingly
soluble in water [2].
Pyriftalid could be prepared by reaction of 2-
chloro-4,6-dimethoxypyrimidine with 7-mer-
capto-3-methyl-2-benzoffuranr-1(3H)-one [54].
Pyriftalid is used to control grass weeds in rice
and other crops.
Formulation. Granules, water soluble
packs.
Weed Control, 2. Individual Herbicides 295
Trade Names. A1-Agent, Junbo Apiro-
fain D.
Pyriftalid decays in soil with a half-life of
12.5 d.
Quinoclamine [2797-51-5], 2-amino-3-
chloro-1,4-naphthoquinone, C10H6ClNO2, Mr
207.62, mp 201
C, log Kow 1.58, r 1.55 g/mL,
vapor pressure 7.0 mPa, is a yellow crystalline
product which is sparingly soluble in water, and
soluble in ethyl acetate, methanol, p-xylene, and
n-heptane [1, 2, 459, 460].
Quinoclamine is used post-emergence to con-
trol a range of weeds, including liverworts and
duckweed.
Formulation. Wettable powder, granules.
Trade Names. Mogeton, Mogeton Moos-Frei.
Quinoclamine decays with half-lives of 22,
22, and 15 d in soil, photolytically, and in water-
sediment, respectively. It is stable towards
hydrolysis.
Tridiphane [58138-08-2], (RS)-2-(3,5-di-
chlorophenyl)-2-(2,2,2-trichloroethyl)oxirane,
C10H7Cl5O, Mr 320.43, mp 106
C, log Kow 4.83,
r 1.58 g/mL, vapor pressure 0.293 mPa, is a
colorless crystalline solid which is sparingly
soluble in water, and moderately soluble in ace-
tone, xylene, and dichloromethane [2].
Tridiphane can be prepared by reaction of 2-
(3,5-dichlorophenyl)-3-trichloroprop-1-ene with
peracetic acid in the presence of sodium acetate
trihydrate [457].
Tridiphane is a new selective nonsystemic
herbicide used to control annual grass seedlings
and broad-leaved weeds in corn and maize.
Formulation. Emulsifiable concentrate.
Trade Names. Tridiphan, Dowco, Tandem.
Tridiphane decays in soil and photolytically
with half-lives of 28 d.
296 Weed Control, 2. Individual Herbicides Vol. 39

2. Toxicology Ecological [1, 2, 7, 8]:

2.1. Diphenyl Ethers LD50 (bobwhite quail, oral) 2000 mg/kg

LC50 (rainbow trout, 96-h) 0.67 mg/L
EC50 (daphnia magna, 48-h) 1.2 mg/L
Acifluorfen [50594-66-6], (sodium salt: EC50 (algae, 72-h) 0.47 mg/L
[62476-59-9]) LD50 (honeybee, contact) 100 mg/bee
Mammalian [15, 461]: LC50 (earthworm, 14-days) 150 mg/kg soil

LD50 (rat, oral) 1540-4790 mg/kg

LD50 (mice, oral) 1370 mg/kg AKH-7088 [104459-82-7]
LD50 (rabbit, oral) 1590-3250 mg/kg Mammalian [1, 10]:
LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 6.91 mg/L air
LD50 (rat, oral) 5000 mg/kg
Rabbit: moderately
LD50 (rat, dermal) 2000 mg/kg
irritating to skin
Rabbit: moderately irritating to skin
Rabbit: severely
Rabbit: nonirritating to eyes
irritating to eyes
Nonmutagenic
Guinea pig: not a sensitizer
Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) 1.25 mg kg1 d1 Bifenox [42576-02-3]
(developmental)
Rat (teratogenicity, gavage) 90 mg kg1 d1
Mammalian [13, 12, 13, 461, 462]:
(maternal)
Rat (teratogenicity, gavage) 20 mg kg1 d1 LD50 (rat, oral) > 5000 mg/kg
(developmental) LD50 (mouse, oral) > 4556 mg/kg
Rabbit (teratogenicity, gavage) > 36 mg kg1 d1 LD50 (rabbit, dermal) > 2000 mg/kg
(maternal and LC50 (rat, 4-h inhalation) > 0.91 mg/L air
developmental) Rabbit: nonirritating to skin and eyes
Rat (2-year feed) 25 mg kg1 d1 Nonmutagenic
Dog (2-year feed) 1.25 mg kg1 d1 NOEL/NOAEL:
Mouse (18-month feed) 1 mg kg1 d1 Rabbit (teratogenicity, gavage) 160 mg kg1 d1
ADI/RfD 0.013 mg kg1 d1 (maternal)
Rat (2-generation feed) >500 mg kg1 d1
3 (developmental)
mg kg1 d1
Ecological [1, 5]: Rat (2-year feed) 80 mg kg1 d1
Dog (1-year capsules) >25 mg kg1 d1
LD50 (mallard duck, oral) 2821 mg/kg Mouse (2-year feed) ca. 30 mg kg1 d1
LC50 (rainbow trout, 96-h) 54 mg/L Mouse (18-month feed) 50 mg kg1 d1
EC50 (daphnia magna, 48-h) 28 mg/L ADI 0.3 mg kg1 d1
LD50 (honeybee, oral) >100 mg/bee ARfD 0.5 mg kg1 d1

Aclonifen [74070-46-5] Ecological [13, 13]:

Mammalian [1, 2, 7, 8, 461]:
LD50 (bobwhite quail, oral) 2000 mg/kg
LD50 (rat, oral) > 5000 mg/kg LC50 (rainbow trout, 96-h) 0.67 mg/L
LD50 (mouse, oral) > 5000 mg/kg EC50 (daphnia magna, 48-h) 0.66 mg/L
LD50 (rat, dermal) > 5000 mg/kg EC50 (algae, 72-h) 0.00018 mg/L
LC50 (rat, 4-h inhalation) > 5.06 mg/L air LD50 (honeybee, contact) 200 mg/bee
Rabbit: slightly irritating to skin LC50 (earthworm, 14-d) 1000 mg/kg soil
Rabbit: slightly irritating to eyes
Guinea pig: not sensitizing
Nonmutagenic
NOEL/NOAEL Chlomethoxyfen [32861-85-1]
Rat (2-generation feed) 130 mg kg1 d1 Mammalian [1, 2]:
Rat (90-day feed) 1.4 mg kg1 d1
Dog (6-month feed) 3 mg kg1 d1
ADI/AOEL: 0.07 mg kg1 d1 LD50 (rat, oral) 18000 mg/kg
LD50 (mouse, oral) 33 000 mg/kg
Vol. 39 Weed Control, 2. Individual Herbicides 297
LD50 (rat, dermal) > 5000 mg/kg
LC50 (rat, 4-h inhalation) > 1.77 mg/L air
Ecological [1, 2, 18]:
Rat (teratogenicity, gavage) 500 mg kg1 d1
(maternal and LD50 (bobwhite quail, oral) 1418 mg/kg
developmental) LC50 (rainbow trout, 96-h) 23 mg/L
EC50 (daphnia magna, 48-h) 30 mg/L
EC50 (algae, 72-h) 0.00018 mg/L
LD50 (honeybee, contact) >100 mg/bee
Ecological [1, 2]: LC50 (earthworm, 14-d) 6 mg/kg soil

LC50 (carp, 96-h) 237 mg/L

LD50 (mayfly, 48-h) 40 mg/L Fomesafen [72178-02-0]
LC50 (toad, 96-h) 40 mg/L Mammalian [13, 21, 22, 463]:

LD50 (rat, oral) 12502000 mg/kg

Ethoxyfen-ethyl [131086-42-5] LD50 (rabbit, dermal) 1600 mg/kg
Mammalian [2, 16]: LC50 (rat, 4-h inhalation) 4.97 mg/L air
Rabbit: mildly irritating to skin
Rabbit: moderately irritating to eyes
Guinea pig: a potential skin sensitizer
LD50 (rat, oral) 843963 mg/kg Nonmutagenic
LD50 (mouse, oral) 11131269 mg/kg NOEL/NOAEL:
LD50 (rat, dermal) > 5000 mg/kg Rabbit (teratogenicity, gavage) 2.5 mg kg1 d1
LD50 (rabbit, dermal) > 2000 mg/kg (developmental)
LC50 (rat, 14-d inhalation) 9.34 mg/L air Rat (2-year feed) 0.25 mg kg1 d1
Rabbit: mildly irritating to skin Dog (6-month feed) 1.0 mg kg1 d1
Rabbit: moderately irritating to eyes Mouse (2-year feed) 1.0 mg kg1 d1
Guinea pig: not a sensitizer ADI 0.0025 mg kg1 d1
Nonmutagenic

Ecological [13, 21, 22]:

Fluoroglycofen-ethyl [77501-90-7]
Mammalian [1, 2, 18, 462]
LD50 (mallard duck, oral) 5000 mg/kg
LC50 (rainbow trout, 96-h) 170 mg/L
EC50 (daphnia magna, 48-h) 330 mg/L
EC50 (algae, 72-h) 0.17 mg/L
LD50 (rat, oral) 1500 mg/kg LD50 (honeybee, oral) 50 mg/bee
LD50 (rabbit, dermal) > 5000 mg/kg LC50 (earthworm, 14-days) 1000 mg/kg soil
LC50 (rat, 4-h inhalation) > 7.5 mg/L air
Rabbit: slightly irritating to skin
Rabbit: moderately irritating to eyes
Guinea pig: not a skin sensitizer
Nonmutagenic Lactofen [77501-63-4]
NOEL/NOAEL: Mammalian [13, 5, 24, 464466]:
Rat (teratogenicity, gavage) 18 mg kg1 d1
(maternal)
Rat (teratogenicity, gavage) >200 mg kg1 d1 LD50 (rat, oral) > 5000 mg/kg
(developmental) LD50 (rat, dermal) > 2000 mg/kg
Rabbit (teratogenicity, gavage) 30 mg kg1 d1 LC50 (rat, 4-h inhalation) 5.3 mg/L air
(maternal, Rabbit: severely irritating to skin
developmental) Rabbit: irritating to eye
Rat (3-generation feed) 2 mg kg1 d1 Nonmutagenic
(parental) NOEL/NOAEL:
Rat (3-generation feed) 40 mg kg1 d1 Rat (2-generation feed) 2.5 mg kg1 d1
(developmental) (parental and
Rat (2-year feed) 0.951.26 mg kg1 d1 developmental)
Dog (1-year feed) 8.99.9 mg kg1 d1 Rat (teratogenicity, gavage) 50 mg kg1 d1
Mouse (18-month feed) 1.41.9 mg kg1 d1 (maternal and
ADI: 0.0095 mg kg1 d1 developmental)
AOEL 0.08 mg kg1 d1 Rabbit (teratogenicity, gavage) 4 mg kg1 d1
(maternal)
298 Weed Control, 2. Individual Herbicides Vol. 39
1 1
> 20 mg kg d NOEL/NOAEL:
(developmental) Rat (2-generation feed) 5 mg kg1 d1
Chimpanzees (93-day capsule) 75 mg kg1 d1 (parental)
Rat (2-year feed) 25 mg kg1 d1 20 mg kg1 d1
Dog (1-year feed) 5 mg kg1 d1 (developmental)
Mouse (18-month feed) 1.5 mg kg1 d1 Rat (teratogenicity, gavage) 15 mg kg1 d1
ADI/RfD: 0.002 mg kg1 d1 (maternal)
Rabbit (teratogenicity, gavage) 10 mg kg1 d1
(maternal)
Rat (2-year feed) 2 mg kg1 d1
Ecological [13, 5, 24, 465]: Dog (2-year feed) 2.5 mg kg1 d1
Mouse (20-month feed) 0.3 mg kg1 d1
ADI/RfD: 0.003 mg kg1 d1
LD50 (bobwhite quail, oral) 2510 mg/kg ARfD 0.30 mg kg1 d1
LC50 (bluegill sunfish, 96-h) 100 mg/L AOEL 0.013 mg kg1 d1
EC50 (daphnia magna, 48-h) 8.4 mg/L
LD50 (honeybee, contact) 160 mg/bee

Ecological [13, 28, 29]:

Nitrofen [1836-75-5]
Mammalian [2, 3, 26, 27]: LD50 (bobwhite quail, oral) 947 mg/kg
LC50 (rainbow trout, 96-h) 0.25 mg/L
EC50 (daphnia magna, 48-h) 0.72 mg/L
LD50 (rat, oral) 116740 mg/kg EC50 (algae, 72-h) 2.0 mg/L
LD50 (rabbit, oral) 16202630 mg/kg LD50 (honeybee, contact) 100 mg/bee
LD50 (mouse, oral) 450 mg/kg LC50 (earthworm, 14-d) 1000 mg/kg soil
LD50 (rat, dermal) 5000 mg/kg
LC50 (rat, 4-h inhalation) 205 mg/L air
Rabbit: skin and eye irritant
Guinea pig: skin sensitizer
NOEL/NOAEL:
Rat (13-week feed) 5 mg kg1 d1 2.2. Sulfonylureas
Dog (13-week feed) 5 mg kg1 d1
Rat (2-generation rat) 20 mg kg1 d1 Amidosulfuron [120923-37-7]
(parental)
Mammalian [1, 2, 32, 33]:
Rat (2-generation rat) 186 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) 80 mg kg1 d1
ADI: not assigned LD50 (rat, oral) > 5000 mg/kg
LD50 (mouse, oral) > 5000 mg/kg
LD50 (rat, dermal) > 5000 mg/kg
LC50 (rat, 4-h inhalation) > 1.8 mg/L air
Ecological [2, 3, 26]: Rabbit: nonirritating to skin and eyes
Guinea pig: not a skin sensitizer
Nonmutagenic
LC50 (rainbow trout, 96-h) 7 mg/L NOEL/NOAEL:
EC50 (daphnia magna, 48-h) 40 mg/L Rat (2-year feed) 19.5 mg kg1 d1
Mouse (90-d feed) 97.## mg kg1 d1
ADI 0.2 mg kg1 d1
AOEL 1.4 mg kg1 d1
Oxyfluorfen [42874-03-3]
Mammalian [13, 29, 30, 462]:

LD50 (rat, oral) > 5000 mg/kg Ecological [1, 2]:

LD50 (mouse, oral) 27005900 mg/kg
LD50 (dog, oral) > 5000 mg/kg
LD50 (rat, dermal) > 5000 mg/kg LD50 (bobwhite quail) 2000 mg/kg
LD50 (rabbit, dermal) > 10 000 mg/kg LC50 (rainbow trout, 96-h) 320 mg/L
LC50 (rat, 4-h inhalation) > 5.4 mg/L air EC50 (daphnia magna, 48-h) 36 mg/L
Rabbit: mildly irritating to skin EC50 (algae, 72-h) 47 mg/L
Rabbit: moderately irritating to eyes LD50 (honeybee, contact) 100 mg/bee
Guinea pig: not a skin sensitizer LC50 (earthworm, 14-days) 1000 mg/kg soil
Nonmutagenic
Vol. 39 Weed Control, 2. Individual Herbicides 299

Azimsulfuron [120162-55-2] Ecological [1, 2, 38]:

Mammalian [1, 2, 35, 36, 461]:
LD50 (mallard duck, oral) 2510 mg/kg
LC50 (rainbow trout, 96-h) 66 mg/L
LD50 (rat, oral) > 5000 mg/kg EC50 (daphnia magna, 48-h) 130 mg/L
LD50 (rat, dermal) > 2000 mg/kg EC50 (algae, 72-h) 0.02 mg/L
LC50 (rat, 4-h inhalation) > 5.94 mg/L air LD50 (honeybee, oral) 51.4 mg/bee
Rabbit: nonirritating to skin and eyes LC50 (earthworm, 14-days) 1000 mg/kg soil
Guinea pig: not a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
Rat (2-year feed) mg kg1 d1 Chlorimuron-ethyl [90982-32-4]
Dog (1-year feed) 17.8 mg kg1 d1
Rat (2-generation feed) 10 mg kg1 d1
Mammalian [13, 40, 462, 468]:
(parental)
Rat (2-generation feed) 76 mg kg1 d1
(developmental) LD50 (rat, oral) 41024236 mg/kg
Rat (teratogenicity, gavage) 200 mg kg1 d1 LD50 (rabbit, dermal) > 2000 mg/kg
(maternal and LC50 (rat, 4-h inhalation) > 5.6 mg/L air
developmental) Rabbit: mildly irritating to
ADI: 0.1 mg kg1 d1 skin and eyes
AOEL 0.2 mg kg1 d1 Guinea pig: not a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) 12.5 mg kg1 d1
(parental)
Ecological [1, 2, 35]: Rat (2-generation feed) 1.25 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) 30 mg kg1 d1
LD50 (bobwhite quail, oral) 2250 mg/kg (maternal)
LC50 (rainbow trout, 96-h) 154 mg/L Rat (teratogenicity, gavage) 150 mg kg1 d1
EC50 (daphnia magna, 48-h) 941 mg/L (developmental)
EC50 (algae, 72-h) 0.012 mg/L Rabbit (teratogenicity, gavage) 60 mg kg1 d1
LD50 (honeybee, oral) 25 mg/bee (maternal)
LC50 (earthworm, 14-days) 1000 mg/kg soil Rabbit (teratogenicity, gavage) 300 mg kg1 d1
(developmental)
Rat (2-year feed) 12.5 mg kg1 d1
Dog (1-year feed) 6.25 mg kg1 d1
Bensulfuron-methyl [83055-99-6] Mouse (18-month feed) 3.75 mg kg1 d1
Mammalian [1, 2, 38, 462, 467]: ADI: 0.020.062 mg kg1 d1

LD50 (rat, oral) > 5000 mg/kg

LD50 (mouse, oral) > 10 985 mg/kg Ecological [13, 40]:
LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 7.5 mg/L air
Rabbit: nonirritating to skin and eyes LD50 (mallard duck, oral) 2510 mg/kg
Guinea pig: not a skin sensitizer LC50 (rainbow trout, 96-h) 1000 mg/L
Nonmutagenic EC50 (daphnia magna, 48-h) 1000 mg/L
NOEL/NOAEL: LD50 (honeybee, contact) 12.5 mg/bee
Rat (2-generation feed) ca. 20 mg kg1 d1 LC50 (earthworm, 14-d) 4050 mg/kg soil
(parental)
Rat (teratogenicity, gavage) 2000 mg kg1 d1
(maternal)
Rat (teratogenicity, gavage) 500 mg kg1 d1 Chlorsulfuron [64902-72-3]
(developmental) Mammalian [13, 43, 44, 462]:
Rabbit (teratogenicity, gavage) 300 mg kg1 d1
(maternal and
developmental)
LD50 (rat, oral) 55456293 mg/kg
Rat (2-year feed) 21.4 mg kg1 d1
LD50 (guinea pig, oral) 1363 mg/kg
Dog (1-year feed) ca. 20 mg kg1 d1
LD50 (dog, oral) > 2500 mg/kg
Mouse (2-year feed) ca. 455 mg kg1 d1
LD50 (rabbit, dermal) 25003400 mg/kg
ADI: 0.2 mg kg1 d1
LC50 (rat, 4-h inhalation) 5.5 mg/L air
300 Weed Control, 2. Individual Herbicides Vol. 39
Rabbit: nonirritating to skin
Rabbit: mildly irritating to eyes
Ecological [1, 2]:
Guinea pig: not a skin sensitizer
Nonmutagenic
LD50 (Japanese quail, oral) 2000 mg/kg
NOEL/NOAEL:
LC50 (rainbow trout, 96-h) 100 mg/L
Rat (3-generation feed) 125 mg kg1 d1
EC50 (daphnia magna, 48-h) 250 mg/L
(parental)
EC50 (algae, 72-h) 4.8 mg/L
Rat (3-generation feed) 5 mg kg1 d1
LD50 (honeybee, oral) 100 mg/bee
(developmental)
LC50 (earthworm, 14-d) 1000 mg/kg soil
Rat (teratogenicity, gavage) 165 mg kg1 d1
(maternal)
Rat (teratogenicity, gavage) 500 mg kg1 d1
(developmental)
Rabbit (teratogenicity, gavage) 75 mg kg1 d1
Cyclosulfamuron [136849-15-5]
(maternal) Mammalian [1, 2, 461]:
Rabbit (teratogenicity, gavage) 200 mg kg1 d1
(developmental)
Rat (2-year feed) 5 mg kg1 d1 LD50 (rat, oral) > 5000 mg/kg
Dog (1-year feed) 60.6 mg kg1 d1 LD50 (mouse, oral) > 5000 mg/kg
Mouse (78-week feed) 108 mg kg1 d1 LD50 (rabbit, dermal) > 4000 mg/kg
ADI: 0.20.05 mg kg1 d1 LC50 (rat, 4-h inhalation) > 5.2 mg/L air
Rabbit: nonirritating to skin
Rabbit: mildly irritating to eyes
Nonmutagenic
NOEL/NOAEL:
Ecological [13, 43, 44]: Rat (2-year feed) 50 mg kg1 d1
Dog (1-year feed) 3 mg kg1 d1
ADI 1.25 mg kg1 d1
LD50 (mallard duck, oral) 5000 mg/kg
LC50 (rainbow trout, 96-h) 122 mg/L
EC50 (daphnia magna, 48-h) 112 mg/L
EC50 (algae, 72-h) 0.068 mg/L
Ecological [1, 2]:
LD50 (honeybee, contact) 100 mg/bee
LC50 (earthworm, 14-d) 750 mg/kg soil
LD50 (bobwhite quail, oral) 1880 mg/kg
LC50 (rainbow trout, 96-h) 7.7 mg/L
EC50 (daphnia magna, 48-h) 9.1 mg/L
Cinosulfuron [94593-91-6] EC50 (algae, 72-h) 0.00044 mg/L
Mammalian [1, 469, 470]: LD50 (honeybee, oral) 99 mg/bee
LC50 (earthworm, 14-d) 892 mg/kg soil

LD50 (rat, oral) > 5000 mg/kg

LD50 (mouse, oral) > 5000 mg/kg
LD50 (rat, dermal) > 2000 mg/kg Ethametsulfuron-methyl [97780-06-8]
LC50 (rat, 4-h inhalation) > 5.0 mg/L air Mammalian [1, 2, 462, 471, 472]:
Rabbit: nonirritating to skin and eyes
Guinea pig: not a skin sensitizer
Nonmutagenic LD50 (rat, oral) > 5000 mg/kg
NOEL/NOAEL: LD50 (rabbit, oral) > 5000 mg/kg
Rat (2-generation feed) 12.5 mg kg1 d1 LD50 (rabbit, dermal) > 2000 mg/kg
(parental) LC50 (rat, 4-h inhalation) > 5.7 mg/L air
Rat (teratogenicity, gavage) 200 mg kg1 d1 Rabbit: nonirritating to skin
(maternal) Rabbit: strongly irritating to eyes
Rat (teratogenicity, gavage) > 2400 mg kg1 d1 Guinea pig: not a skin sensitizer
(developmental) Nonmutagenic
Rabbit (teratogenicity, gavage) 15 mg kg1 d1 NOEL/NOAEL:
(maternal) Rat (2-generation feed) 433 3 mg kg1 d1
Rabbit (teratogenicity, gavage) 30 mg kg1 d1 (parental,
(developmental) developmental)
Rat (2-year feed) 12.5 mg kg1 d1 Rat (teratogenicity, gavage) 1000 mg kg1 d1
Dog (1-year feed) 6.25 mg kg1 d1 (maternal,
Mouse (2-year feed) ca. 60404 mg kg1 d1 developmental)
ADI 0.02 mg kg1 d1 Rabbit (teratogenicity, gavage) 250 mg kg1 d1
(maternal)
Vol. 39 Weed Control, 2. Individual Herbicides 301
1 1
Rabbit (teratogenicity, gavage) 1000 mg kg d Rabbit: moderately
(developmental) irritating to eyes
Rat (2-year feed) 238.5 mg kg1 d1 Guinea pig: a skin
Dog (1-year feed) 87 mg kg1 d1 sensitizer
Mouse (18-month feed) 818 mg kg1 d1 Nonmutagenic
ADI 0.20.87 mg kg1 d1 NOEL/NOAEL:
RfD 4.5 mg kg1 d1 Rat (2-year feed) 1.3 mg kg1 d1
Dog (1-year capsules) 2 mg kg1 d1
Mouse (78-week feed) 77.3 mg kg1 d1
Rat (2-generation feed) 8.7 (parental mg kg1 d1
Ecological [1, 2]: Rat (2-generation feed) 473 (developmental) mg kg1 d1
ADI/RfD 0.013 mg kg1 d1
ARfD 0.5 mg kg1 d1
LD50 (bobwhite quail, oral) >2250 mg/kg AOEL 0.02 mg kg1 d1
LC50 (rainbow trout, 96-h) >600 mg/L
EC50 (daphnia magna, 48-h) 550 mg/L
EC50 (algae, 5-d) 2.6 mg/L
LD50 (honeybee, oral) 100 mg/L
Ecological [1, 2, 51]:
LC50 (earthworm, 14-d) >1000 mg/kg soil
LD50 (bobwhite quail, oral) 2000 mg/kg
LC50 (salmon, 96-h) 22 mg/L
EC50 (daphnia magna, 48-h) 25 mg/L
Ethoxysulfuron [126801-58-9] EC50 (algae, 72-h) 0.014 mg/L
Mammalian [1, 2, 49]: LD50 (honeybee, oral) 100 mg/bee
LC50 (earthworm, 14-d) 15.75 mg/kg soil

LD50 (rat, oral) > 3270 mg/kg

LD50 (rat, dermal) > 4000 mg/kg
LC50 (rat, 4-h inhalation) 3.55 mg/L air
Flucetosulfuron [412928-75-7]
Rabbit: irritating to skin and eyes Mammalian [1]:
Nonmutagenic
NOEL/NOAEL:
LD50 (rat, oral) 5000 mg/kg
Dog (1-year feed) 5.6 mg kg1 d1
Rat (2-year feed) 40 mg kg1 d1
Mouse (78-week feed) 3.9 mg kg1 d1
Rat (teratogenicity, gavage) 59 mg kg1 d1 Ecological [1]:
Rat (teratogenicity, gavage) 200 mg kg1 d1
Rabbit (teratogenicity, gavage) 63 mg kg1 d1
ADI 0.04 mg kg1 d1 LC50 (carp, 96-h) 20 mg/L
AOEL 0.06 mg kg1 d1 EC50 (daphnia magna, 48-h) 10 mg/L
EC50 (algae, 72-h) 10 mg/L

Ecological [1, 2, 49]:

Flupyrsulfuron-methyl-sodium [144740-
54-5]
LD50 (bobwhite quail, oral) 2000 mg/kg Mammalian [1, 2, 55, 461]:
LC50 (rainbow trout, 96-h) 80 mg/L
EC50 (daphnia magna, 48-h) 307 mg/L
EC50 (algae, 72-h) 0.19 mg/L LD50 (rat, oral) > 5000 mg/kg
LD50 (honeybee, contact) 200 mg/bee LD50 (mouse, oral) > 5000 mg/kg
LC50 (earthworm, 14-d) 1000 mg/kg soil LD50 (rat, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 2.0 mg/L air
Rabbit: irritating to skin and eyes
Guinea pig: a skin sensitizer
Flazasulfuron [104040-78-0] Nonmutagenic
NOEL/NOAEL:
Mammalian [1, 2, 51, 52, 461]: Mouse (18-month feed) 3.51 mg kg1 d1
Rat (2-generation, feed) 84 mg kg1 d1
Rat (teratogenicity, gavage) 20 mg kg1 d1
LD50 (rat, oral) > 5000 mg/kg Rat (2-year feed) 17.5 mg kg1 d1
LD50 (mouse, oral) > 5000 mg/kg Dog (1-year feed) 13.6 mg kg1 d1
LD50 (rat, dermal) > 2000 mg/kg ADI: 0.035 mg kg1 d1
LC50 (rat, 4-h inhalation) 5.99 mg/L air AOEL 0.08 mg kg1 d1
Rabbit: irritating to skin
302 Weed Control, 2. Individual Herbicides Vol. 39
Rabbit (teratogenicity, gavage) 50 mg kg d1
1
Ecological [1, 2, 55]: (maternal,
developmental)
LD50 (bobwhite quail, oral) 2250 mg/kg Rat (2-generation feed) 50.5 mg kg1 d1
LC50 (salmon, 96-h) 470 mg/L (parental)
EC50 (daphnia magna, 48-h) 721 mg/L Rat (2-generation feed) 261.4 mg kg1 d1
EC50 (algae, 72-h) 0.0037 mg/L (developmental)
LD50 (honeybee, contact) 25 mg/bee Rat (2-year feed) 56.3108.3 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil Dog (1-year feed) 10 mg kg1 d1
Mouse (18-month feed) 4101214 mg kg1 d1
ADI 0.1 mg kg1 d1
RfD 0.03 mg kg1 d1
Foramsulfuron [173159-57-4] ARfD 0.17 mg kg1 d1
Mammalian [2, 57, 58]:

LD50 (rat, oral) >5000 mg/kg Ecological [1, 2, 473]:

LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 5.04 mg/L air
LD50 (bobwhite quail, oral) 2250 mg/kg
Rabbit: not a skin irritant
LC50 (rainbow trout, 96-h) 131 mg/L
Rabbit: mildly irritating to eyes
EC50 (daphnia magna, 48-h) 107 mg/L
Guinea pig: not a skin sensitizer
EC50 (algae, 72-h) 0.0053 mg/L
Nonmutagenic
LD50 (honeybee, contact) 100 mg/bee
NOEL/NOAEL:
LC50 (earthworm, 14-d) 1000 mg/kg soil
Rat (2-generation feed) 1038 mg kg1 d1
(parental,
developmental)
Rat (teratogenicity, gavage) 1000 mg kg1 d1
(maternal,
Imazosulfuron [122548-33-8]
developmental) Mammalian [1, 2, 474]:
Rabbit (teratogenicity, gavage) 500 mg kg1 d1
(maternal,
LD50 (rat, oral) > 5000 mg/kg
developmental)
LD50 (mouse, oral) > 5000 mg/kg
Rat (2-year feed) 849 mg kg1 d1
LD50 (rat, dermal) > 2000 mg/kg
Mouse (78-week feed) 11151358 mg kg1 d1
LC50 (rat, 4-h inhalation) > 2.4 mg/L air
RfD 8.5 mg kg1 d1
Rabbit: nonirritating to skin and eyes
Guinea pig: not a skin sensitizer
Nonmutagenic
Ecological [2]: NOEL/NOAEL:
Rat (2-generation feed) 77.8 mg kg1 d1
(parental)
LD50 (bobwhite quail, oral) 2000 mg/kg Rat (teratogenicity, gavage) 1000 mg kg1 d1
LC50 (salmon, 96-h) 100 mg/L (maternal)
EC50 (daphnia magna, 48-h) 100 mg/L Rat (teratogenicity, gavage) 1500 mg kg1 d1
EC50 (algae, 72-h) 3.3 mg/L (developmental)
LD50 (honeybee, oral) 226 mg/bee Rabbit (teratogenicity, gavage) 50 mg kg1 d1
LC50 (earthworm, 14-d) 453 mg/kg soil (maternal)
Rat (teratogenicity, gavage) 125 mg kg1 d1
(developmental)
Rat (2-year feed) 106 mg kg1 d1
Halosulfuron-methyl [100784-20-1] Dog (1-year feed) 75 mg kg1 d1
Mammalian [1, 2, 473]: Mouse (18-month feed) 72.7 mg kg1 d1
ADI: 0.7 mg kg1 d1

LD50 (rat, oral) 1287 mg/kg

LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) 5.7 mg/L air Ecological [1, 2]:
Rabbit: nonirritating to skin
Rabbit: slightly irritating to eyes
Guinea pig: not a skin
sensitizer Nonmutagenic LD50 (mallard duck, oral) 2250 mg/kg
NOEL/NOAEL: LC50 (carp, 96-h) 10 mg/L
Rat (teratogenicity, gavage) 250 mg kg1 d1 EC50 (daphnia magna, 48-h) 40 mg/L
(maternal, LD50 (honeybee, oral) 48.2 mg/bee
developmental)
Vol. 39 Weed Control, 2. Individual Herbicides 303
ADI 1.0 mg kg d1
1
Iodosulfuron-methyl Sodium [144550-36-7] AOEL 0.2 mg kg1 d1
Mammalian [2, 61, 62, 475]: RfD 1.55 mg kg1 d1

LD50 (rat, oral) 2678 mg/kg

LD50 (rat, dermal) >2000 mg/kg Ecological [2, 63, 64]:
LC50 (rat, 4-h inhalation) 2.8 mg/L air
Rabbit: irritating to skin and eyes
Guinea pig: a skin sensitizer LD50 (mallard duck, oral) >2000 mg/kg
Nonmutagenic LC50 (rainbow trout, 96-h) 100 mg/L
NOEL/NOAEL: EC50 (daphnia magna, 48-h) 100 mg/L
Rat (teratogenicity, gavage) 315 mg kg1 d1 EC50 (algae, 72-h) 0.2 mg/L
(maternal, LD50 (honeybee, oral) 5.6 mg/bee
developmental) LC50 (earthworm, 14-d) 1000 mg/kg soil
Rabbit (teratogenicity, gavage) 400 mg kg1 d1
(maternal,
developmental)
Rat (2-generation feed) 346 mg kg1 d1 Metazosulfuron [868680-84-6] New herbi-
(parental, cide, no data are yet available.
developmental)
Dog (1-year feed) 7.2541.8 mg kg1 d1
Rat (2-year feed) 29.739.1 mg kg1 d1 Metsulfuron-methyl [74223-64-6]
Mouse (78-week feed) 54.257.6 mg kg1 d1 Mammalian [13, 5, 67, 68, 462]:
RfD 0.073 mg kg1 d1
ARfD 3.15 mg kg1 d1
LD50 (rat, oral) > 5000 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 5.0 mg/L air
Ecological [2, 61, 62]: Rabbit: moderately irritating to eyes
Guinea pig: mildly irritating to skin
Guinea pig: a skin sensitizer
LD50 (bobwhite quail, oral) 2000 mg/kg Nonmutagenic
LC50 (bluegill sunfish, 96-h) 100 mg/L NOEL/NOAEL:
EC50 (daphnia magna, 48-h) 100 mg/L Rat (2-generation feed) 3443 mg kg1 d1
EC50 (algae, 72-h) 0.07 mg/L (parental)
LD50 (honeybee, oral) 80 mg/bee Rat (2-generation feed) 342475 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil (developmental)
Rat (teratogenicity, gavage) 250 mg kg1 d1
(maternal)
Rat (teratogenicity, gavage) 1000 mg kg1 d1
Mesosulfuron-methyl [208465-21-8] (developmental)
Mammalian [2, 63, 64]: Rabbit (teratogenicity, gavage) 25 mg kg1 d1
(maternal)
Rabbit (teratogenicity, gavage) 700 mg kg1 d1
LD50 (rat, oral) >5000 mg/kg (developmental)
LD50 (rat, dermal) >5000 mg/kg Rat (2-year feed) 25 mg kg1 d1
LC50 (rat, 4-h inhalation) 1.33 mg/L air Dog (1-year feed) 125 mg kg1 d1
Rabbit: not a skin irritant Mouse (18-month feed) 666836 mg kg1 d1
Rabbit: slightly irritating to eyes ADI 0.22 mg kg1 d1
Guinea pig: skin sensitizer AOEL 0.7 mg kg1 d1
Nonmutagenic RfD 0.25 mg kg1 d1
NOEL/NOAEL:
Rat (teratogenicity, gavage) 1000 mg kg1 d1
(maternal,
developmental)
Ecological [13, 67, 68]:
Rabbit (teratogenicity, gavage) 1000 mg kg1 d1
(maternal,
developmental) LD50 (mallard duck, oral) 25105000 mg/kg
Rat (2-generation feed) 1175 mg kg1 d1 LC50 (rainbow trout, 96-h) 150 mg/L
(parental, EC50 (daphnia magna, 48-h) 150 mg/L
developmental) EC50 (algae, 72-h) 0.045 mg/L
Dog (1-year feed) 255 mg kg1 d1 LD50 (honeybee, contact) 25>150 mg/bee
Rat (2-year feed) 764952 mg kg1 d1 LC50 (earthworm, 14-d) >1000 mg/kg soil
Mouse (78-week feed) 10691355 mg kg1 d1
304 Weed Control, 2. Individual Herbicides Vol. 39
Mouse (78-week feed) 100 mg kg d1
1
Nicosulfuron [111991-09-4] RfD 0.05 mg kg1 d1
Mammalian [1, 2, 5, 7072, 462, 476]:

LD50 (rat, oral) > 5000 mg/kg Ecological [2, 477]:

LD50 (mouse, oral) > 5000 mg/kg
LD50 (rat, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) 5.9 mg/L air
LD50 (bobwhite quail, oral) 19602000 mg/kg
Rabbit: nonirritating to skin
LC50 (rainbow trout, 96-h) 122 mg/L
Rabbit: moderately irritating to eyes
EC50 (daphnia magna, 48-h) 105 mg/L
Guinea pig: not a skin sensitizer
EC50 (algae, 72-h) 0.813 mg/L
Nonmutagenic
LD50 (honeybee, contact) 109.4 mg/bee
NOEL/NOAEL:
LC50 (earthworm, 14-d) 1000 mg/kg soil
Rat (2-generation feed) 287 mg kg1 d1
(parental and
developmental)
Rat (teratogenicity, feed) 300 mg kg1 d1 Oxasulfuron [144651-06-9]
(maternal and
developmental)
Mammalian [1, 2]:
Rabbit (teratogenicity, feed) 100 mg kg1 d1
(maternal)
LD50 (rat, oral) > 5000 mg/kg
500 mg kg1 d1
LD50 (rabbit, dermal) > 2000 mg/kg
(developmental)
LC50 (rat, 4-h inhalation) > 5.08 mg/L air
Rat (2-year feed) > 786 mg kg1 d1
Rabbit: irritating to skin and eyes
Dog (1-year feed) 125 mg kg1 d1
Guinea pig: a skin sensitizer
Mouse (18-month feed) > 993 mg kg1 d1
NOEL/NOAEL:
ADI 2.0 mg kg1 d1
Rat (2-year feed) 8.3 mg kg1 d1
RfD 1.25 mg kg1 d1
Dog (1-year feed) 1.3 mg kg1 d1
AOEL 0.8 mg kg1 d1
Mouse (18-month feed) 1.5 mg kg1 d1
ADI/AOEL 0.013 mg kg1 d1

Ecological [1, 2, 5, 7072]:

Ecological [1, 2]:
LD50 (bobwhite quail, oral) 2000 mg/kg
LC50 (rainbow trout, 96-h) 65.7 mg/L
EC50 (daphnia magna, 48-h) 90 mg/L LD50 (mallard duck, oral) 2250 mg/kg
EC50 (algae, 72-h) 7.8 mg/L LC50 (bluegill sunfish, 96-h) 111 mg/L
EC50 (daphnia magna, 48-h) 89.4 mg/L
EC50 (algae, 72-h) 0.145 mg/L
LD50 (honeybee, oral) 741 mg/bee
Orthosulfamuron [213464-77-8] LC50 (earthworm, 14-d) 1000 mg/kg soil
Mammalian [2, 74, 75, 477]:

LD50 (rat, oral) 5000 mg/kg Primisulfuron-methyl [86209-51-0]

LD50 (rat, dermal) 5000 mg/kg Mammalian [13, 5, 77, 462, 478]:
LC50 (rat, 4-h inhalation) 2.19 mg/L air
Rabbit: nonirritating to skin and eyes
Guinea pig: not a sensitizer LD50 (rat, oral) > 5050 mg/kg
Nonmutagenic LD50 (rat, dermal) > 2010 mg/kg
NOEL/NOAEL: LD50 (rabbit, dermal) > 2010 mg/kg
Rat (teratogenicity, gavage) 1000 mg kg1 d1 LD50 (mouse, dermal) > 2100 mg/kg
(maternal, LC50 (rat, 4-h inhalation) > 4.8 mg/L air
developmental) Rabbit: practically nonirritating to skin
Rabbit (teratogenicity, gavage) 250 mg kg1 d1 Rabbit: slightly irritating to eyes
(maternal, Guinea pig: not a skin sensitizer
developmental) Nonmutagenic
Rat (2-generation feed) 89111 mg kg1 d1 NOEL/NOAEL:
(parental) Rat (2-generation feed) ca. 65 mg kg1 d1
Rat (2-generation feed) 354388 mg kg1 d1 (parental)
(developmental) Rat (teratogenicity, gavage) 100 mg kg1 d1
Dog (1-year feed) 75 mg kg1 d1 (maternal and
Rat (2-year feed) 5 mg kg1 d1 developmental)
Vol. 39 Weed Control, 2. Individual Herbicides 305
1 1
Rabbit (teratogenicity, gavage) 10 mg kg d
(maternal)
Ecological [1, 2, 81]:
600 mg kg1 d1
(developmental) LD50 (mallard duck, oral) 1000 mg/kg
Rat (2-year feed) 15 mg kg1 d1 LC50 (rainbow trout, 96-h) 160 mg/L
Dog (1-year feed) 25 mg kg1 d1 EC50 (daphnia magna, 48-h) 120 mg/L
Mouse (19-month feed) 40 mg kg1 d1 EC50 (algae, 72-h) 0.0089 mg/L
ADI 0.13 mg kg1 d1 LD50 (honeybee, oral) 100 mg/bee
LC50 (earthworm, 14-d) 1000 mg/kg soil

Ecological [13, 5, 77]:

Pyrazosulfuron-ethyl [93697-74-6]
Mammalian [1, 2, 83, 84]:
LD50 (mallard duck, oral) >2150 mg/kg
EC50 (daphnia magna, 48-h) 260480 mg/L
LD50 (honeybee, contact) >100 mg/bee LD50 (rat, oral) > 5000 mg/kg
LC50 (earthworm, 14-d) 1000 mg/kg soil LD50 (mouse, oral) > 5000 mg/kg
LD50 (rat, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 3.9 mg/L air
Rabbit: nonirritating to skin and eyes
Propyrisulfuron [570415-88-2] Guinea pig: not a skin sensitizer
Ecological [80]: Nonmutagenic
NOEL/NOAEL:
Mouse (18-month feed) 4.3 mg kg1 d1
LC50 (carp, 96-h) >9.6 mg/L Rat (104-week feed) 20 mg kg1 d1
EC50 (daphnia magna. 48-h) >9.6 mg/L ADI 0.043 mg kg1 d1
EC50 (algae, 72-h) >11 mg/L

Ecological [1, 2, 83, 84, 480]:

Prosulfuron [94125-34-5]
LD50 (bobwhite quail, oral) 2250 mg/kg
Mammalian [1, 2, 81, 174, 479]:
LC50 (rainbow trout, 96-h) 180 mg/L
EC50 (daphnia magna, 48-h) 700 mg/L
LD50 (rat, oral) 986 mg/kg EC50 (algae, 72-h) 150 mg/L
LD50 (mouse, oral) 1247 mg/kg LD50 (honeybee, contact) 100 mg/bee
LD50 (rabbit, dermal) > 2000 mg/kg LC50 (earthworm, 14-d) 8000 mg/kg soil
LC50 (rat, 4-h inhalation) > 5.4 mg/L air
Rabbit: irritating to skin and eyes
Guinea pig: a skin sensitizer
Nonmutagenic Rimsulfuron [122931-48-0]
NOEL/NOAEL: Mammalian [1, 2, 86, 87, 481]:
Rat (acute neurotoxicity, gavage) 10 mg/kg
Rat (neurotoxicity, 90-day feed) ca. 13 mg kg1 d1
(systemic) LD50 (rat, oral) > 5000 mg/kg
> 330 mg kg1 d1 LD50 (mouse, oral) > 5000 mg/kg
(neurotoxicity) LD50 (rabbit, dermal) > 2000 mg/kg
Rat (2-generation feed) 13.3 mg kg1 d1 LC50 (rat, 4-h inhalation) > 5.4 mg/L air
(parental and Rabbit: nonirritating to skin
reproduction) Rabbit: moderately irritating to eyes
Rat (teratogenicity, gavage) 200 mg kg1 d1 Guinea pig: not a skin sensitizer
(maternal and Nonmutagenic
developmental) NOEL/NOAEL:
Rabbit (teratogenicity, gavage) 20 mg kg1 d1 Rat (2-generation feed) ca. 200 mg kg1 d1
(maternal, Rat (teratogenicity, gavage) 2000 mg kg1 d1
developmental) (maternal)
Rat (2-year feed) 7.9 mg kg1 d1 Rat (teratogenicity, gavage) > 6000 mg kg1 d1
Dog (1-year feed) 1.84 mg kg1 d1 (developmental)
Mouse (18-month feed) 1062 mg kg1 d1 Rabbit (teratogenicity, gavage) 170 mg kg1 d1
ADI 0.019 mg kg1 d1 (maternal)
RfD 0.02 mg kg1 d1 Rabbit (teratogenicity, gavage) > 500 mg kg1 d1
AOEL 0.06 mg kg1 d1 (developmental)
Rat (2-year feed) ca. 15 mg kg1 d1
306 Weed Control, 2. Individual Herbicides Vol. 39
1 1
Dog (1-year feed) ca. 1.25 mg kg d Rat (2-year feed) 24.4 mg kg1 d1
Mouse (18-month feed) ca. 360 mg kg1 d1 Mouse (18-month feed) 105 mg kg1 d1
ADI 0.1 mg kg1 d1 Rat (2-generation feed) 250 mg kg1 d1
AOEL 0.07 mg kg1 d1 (parental)
Rabbit (teratogenicity, gavage) 1000 mg kg1 d1
(maternal and
developmental)
Ecological [1, 2, 86, 87]: ADI/RfD 0.24 mg kg1 d1
AOEL 1 mg kg1 d1
LD50 (bobwhite quail, oral) 2250 mg/kg
LC50 (rainbow trout, 96-h) 390 mg/L
EC50 (daphnia magna, 48-h) 360 mg/L
EC50 (algae, 72-h) 0.029 mg/L
Ecological [1, 2]:
LD50 (honeybee, contact) 100 mg/bee
LC50 (earthworm, 14-d) 1000 mg/kg soil
LD50 (mallard duck, oral) 2250 mg/kg
LC50 (fish, 96-h) 90 mg/L
EC50 (daphnia magna, 48-h) 102 mg/L
Sulfometuron-methyl [74222-97-2] EC50 (algae, 72-h) 0.221 mg/L
LD50 (honeybee, contact) 25 mg/bee
Mammalian [1, 2, 5, 89, 462]: LC50 (earthworm, 56-d) 0.13 mg/kg soil

LD50 (rat, oral) > 5000 mg/kg

LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 5.3 mg/L air Thifensulfuron-methyl [79277-27-3]
Rabbit: slightly irritating to skin Mammalian [13, 92, 93, 462, 483, 484]:
Rabbit: mildly irritating to eyes
Guinea pig: a skin sensitizer
Nonmutagenic (in vitro) LD50 (rat, oral) > 5000 mg/kg
NOEL/NOAEL: LD50 (mouse, oral) > 5000 mg/kg
1 1
Rat (2-generation feed) ca. 33 mg kg d LD50 (rabbit, dermal) > 2000 mg/kg
Rat (teratogenicity, feed?) 65 mg kg1 d1 LC50 (rat, 4-h inhalation) > 7.9 mg/L air
(maternal) Rabbit: nonirritating to skin
Rabbit (teratogenicity, gavage) > 300 mg kg1 d1 Rabbit: moderately irritating to eyes
Rat (2-year feed) 2.5 mg kg1 d1 Guinea pig: a skin sensitizer
Dog (1-year feed) 9 mg kg1 d1 Nonmutagenic
Dog (1-year feed) ca. 5.7 mg kg1 d1 NOEL/NOAEL:
Mouse (18-month feed) 1.6 mg kg1 d1 Rat (2-generation feed) 125 mg kg1 d1
Mouse (18-month feed) ca. 14.3 mg kg1 d1 Rat (teratogenicity, gavage) 200 mg kg1 d1
ADI 0.02 mg kg1 d1 (maternal)
Rat (teratogenicity, gavage) 350 mg kg1 d1
(developmental)
Rabbit (teratogenicity, gavage) 200 mg kg1 d1
Ecological [1, 2, 5, 89]: (maternal)
Rabbit (teratogenicity, gavage) > 650 mg kg1 d1
LD50 (mallard duck, oral) 5000 mg/kg (developmental)
LC50 (rainbow trout, 96-h) 12.5 mg/L Rat (2-year feed) 0.96 mg kg1 d1
EC50 (daphnia magna, 48-h) 12.5 mg/L Dog (1-year feed) 19.7 mg kg1 d1
LD50 (honeybee, contact) 100 mg/bee Mouse (90-day feed) 979 mg kg1 d1
ADI 0.01 mg kg1 d1
AOEL 0.07 mg kg1 d1

Sulfosulfuron [141776-32-1]
Mammalian [1, 2, 482]:
Ecological [13, 92, 93]:
LD50 (rat, oral) > 5000 mg/kg
LD50 (rat, dermal) > 5000 mg/kg LD50 (mallard duck, oral) 2510 mg/kg
LC50 (rat, 4-h inhalation) 3.0 mg/L air LC50 (rainbow trout, 96-h) 250 mg/L
Rabbit: nonirritating to skin EC50 (daphnia magna, 48-h) 470 mg/L
Rabbit: moderately irritating to eyes EC50 (algae, 72-h) 0.0159 mg/L
Guinea pig: not a skin sensitizer LD50 (honeybee, oral) 0.7 mg/bee
NOEL/NOAEL: LC50 (earthworm, 14-d) 2000 mg/kg soil
Dog (1-year feed) 100 mg kg1 d1
Vol. 39 Weed Control, 2. Individual Herbicides 307
1 1
Rabbit (teratogenicity, gavage) 20 mg kg d
Triasulfuron [82097-50-5] (maternal and
Mammalian [1, 2, 95, 471, 485]: developmental)
Rat (2-year feed) 0.951.2 mg kg1 d1
Dog (1-year feed) 0.798.16 mg kg1 d1
LD50 (rat, oral) > 5000 mg/kg Mouse (18-month feed) 30 mg kg1 d1
LD50 (mouse, oral) > 5000 mg/kg ADI 0.011 mg kg1 d1
LD50 (rat, dermal) > 2000 mg/kg ARfD 0.2 mg kg1 d1
LC50 (rat, 4-h inhalation) > 5.18 mg/L air AOEL 0.07 mg kg1 d1
Rabbit: nonirritating to skin RfD 0.008 mg kg1 d1
Rabbit: non to slightly irritating to eyes
Guinea pig: not a skin sensitizer
NOEL/NOAEL:
Rat (2-generation feed) 50 mg kg1 d1 Ecological [13, 98]:
(parental,
developmental)
Rat (teratogenicity, gavage) 100 mg kg1 d1 LD50 (bobwhite quail, oral) >2250 mg/kg
(maternal) LC50 (rainbow trout, 96-h) 738 mg/L
Rat (teratogenicity, gavage) 300 mg kg1 d1 EC50 (daphnia magna, 48-h) 894 mg/L
(developmental) EC50 (algae, 72-h) 0.11 mg/L
Rabbit (teratogenicity, gavage) 120 mg kg1 d1 LD50 (honeybee, oral) 0.91 mg/bee
(maternal) LC50 (earthworm, 14-d) 1000 mg/kg soil
Rabbit (teratogenicity, gavage) 240 mg kg1 d1
(developmental)
Rat (2-year feed) 32.1 mg kg1 d1
Rat (2-year feed) 0.5 mg kg1 d1
Trifloxysulfuron-sodium [199119-58-9]
Dog (1-year feed) 2.5 mg kg1 d1 Mammalian [1, 100, 486]:
Mouse (78-week feed) 1.2 mg kg1 d1
ADI: 0.012 mg kg1 d1
LD50 (rat, oral) 5000 mg/kg
RfD 0.01 mg kg1 d1
LD50 (rabbit, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation)
Rabbit: skin and eye irritant
Guinea pig: a skin sensitizer
Ecological [1, 2, 95]: Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) 48137 mg kg1 d1
LD50 (bobwhite quail, oral) 2150 mg/kg
(parental)
LC50 (rainbow trout, 96-h) 100 mg/L
Rat (2-generation feed) 633792 mg kg1 d1
EC50 (daphnia magna, 48-h) 100 mg/L
(developmental)
EC50 (algae, 72-h) 0.035 mg/L
Rat (teratogenicity, gavage) 300 mg kg1 d1
LD50 (honeybee, oral) 100 mg/bee
(maternal,
LC50 (earthworm, 14-d) 1000 mg/kg soil
developmental)
Rabbit (teratogenicity, gavage) 100 mg kg1 d1
(maternal)
Rabbit (teratogenicity, gavage) 50 mg kg1 d1
Tribenuron-methyl [101200-48-0] (developmental)
Mammalian [13, 97, 98, 462]: Rat (2-year feed) 20.223.7 mg kg1 d1
Dog (1-year feed) 15 mg kg1 d1
Mouse (78-week feed) 111.5121.2 mg kg1 d1
LD50 (rat, oral) > 5000 mg/kg ADI 0.15 mg kg1 d1
LD50 (rabbit, dermal) > 2000 mg/kg ARfD 6.0 mg kg1 d1
LC50 (rat, 4-h inhalation) > 6.7 mg/L air
Rabbit: nonirritating to skin
Rabbit: mildly irritating to eyes
Guinea pig: not a skin sensitizer Ecological [1, 100]:
Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) 1.25 mg kg1 d1 LD50 (mallard duck, oral) 2000 mg/kg
(parental) LC50 (rainbow trout, 96-h) 103 mg/L
2.5 mg kg1 d1 EC50 (daphnia magna, 48-h) 108 mg/L
(developmental) EC50 (algae, 72-h) 0.0065 mg/L
Rat (teratogenicity, gavage) 20 mg kg1 d1 LD (honeybee, oral) >25 mg/bee
(maternal and LC (earthworm, 14-d) 748 mg/kg soil
developmental)
308 Weed Control, 2. Individual Herbicides Vol. 39
Rat (2-year feed) 4864 mg kg1 d1
Triflusulfuron-methyl [126535-15-7] Dog (1-year feed) 6 mg kg1 d1
Mammalian [1, 2, 101103, 462]: Mouse (78-week feed) 3644 mg kg1 d1
ADI 0.06 mg kg1 d1
AOEL 0.15 mg kg1 d1
LD50 (rat, oral) > 5000 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 5.1 mg/L air
Rabbit: nonirritating to skin Ecological [1, 105]:
Rabbit: moderately irritating to eyes
Guinea pig: not a skin sensitizer
Nonmutagenic LC50 (rainbow trout, 96-h) >100 mg/L
NOEL/NOAEL: EC50 (daphnia magna, 48-h) >100 mg/L
1 1
Rat (2-generation feed) 5.8-7.8 mg kg d EC50 (algae, 72-h) 2.71 mg/L
(parental)
89.5115 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) 120 mg kg1 d1
(maternal) 2.3. Chloroacetanilides
Rat (teratogenicity, gavage) >1000 mg kg1 d1
(developmental) Acetochlor [34256-82-1]
Rabbit (teratogenicity, gavage) 90 mg kg1 d1
(maternal,
Mammalian [13, 106, 487]:
developmental)
Rat (2-year feed) 2.44 mg kg1 d1 LD50 (rat, oral) 21482953 mg/kg
Dog (1-year feed) 26.9 mg kg1 d1 LD50 (rabbit, dermal) 36674166 mg/kg
Mouse (18-month feed) 14.9 mg kg1 d1 LC50 (rat, 4-h inhalation) > 3.0 mg/L air
ADI 0.04 mg kg1 d1 Rabbit: practically
ARfD 1.2 mg kg1 d1 nonirritating to skin and eyes
AOEL 0.04 mg kg1 d1 Guinea pig: a skin sensitizer
RfD 0.024 mg kg1 d1 Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) ca. 30 mg kg1 d1
(parental)
Ecological [1, 2, 101103]: Rat (teratogenicity, gavage) 200 mg kg1 d1
(developmental)
LD50 (bobwhite quail, oral) 2250 mg/kg Rabbit (teratogenicity, gavage) 50 mg kg1 d1
LC50 (rainbow trout, 96-h) 730 mg/L (developmental)
EC50 (daphnia magna, 48-h) 960 mg/L Rat (2-year feed) 10 mg kg1 d1
EC50 (algae, 72-h) 0.046 mg/L Dog (1-year feed) 12 mg kg1 d1
LD50 (honeybee, contact) 100 mg/bee ADI 0.0036 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil ARfD 1.5 mg kg1 d1
AOEL 0.02 mg kg1 d1

Tritosulfuron [142469-14-5] Ecological [13, 5, 106]:

Mammalian [2, 105]:
LD50 (bobwhite quail, oral) 928 mg/kg
LD50 (rat, oral) 4700 mg/kg LC50 (rainbow trout, 96-h) 0.36 mg/L
LD50 (rat, dermal) >2000 mg/kg EC50 (daphnia magna, 48-h) 8.6 mg/L
LC50 (rat, 4-h inhalation) >5.4 mg/L air EC50 (algae, 72-h) 0.00027 mg/L
Rabbit: nonirritating to skin and eyes LD50 (honey bee, oral) 100 mg/bee
Guinea pig: a skin sensitizer LC50 (earthworm, 14-d) 105.5 mg/kg soil
Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) 59 mg kg1 d1
(parental, Alachlor [15972-60-8]
developmental) Mammalian [13, 108110, 462]:
Rat (teratogenicity, gavage) 120 mg kg1 d1
(maternal,
developmental) LD50 (rat, oral) 9301350 mg/kg
Rabbit (teratogenicity, gavage) 150 mg kg1 d1 LD50 (mouse, oral) 1100 mg/kg
(maternal, LD50 (rabbit, dermal) 13 300 mg/kg
developmental) LC50 (rat, 4-h inhalation) 1.04 mg/L air
Vol. 39 Weed Control, 2. Individual Herbicides 309
Rabbit: nonirritating to skin
Rabbit: slightly to moderately
Diethatyl-ethyl [38725-95-0]
irritating to eyes Mammalian [111]:
Guinea pig: not a skin sensitizer
Mutagenicity
NOEL/NOAEL: LD50 (rat, oral) 23003700 mg/kg
Rat (3-generation feed) 10 mg kg1 d1 LD50 (rabbit, dermal) 4000 mg/kg
(parental) LC50 (rat, 4-h inhalation) >4.56 mg/L air
Rat (teratogenicity, gavage) 150 mg kg1 d1 Rabbit: minimally irritating to skin
(maternal and NOEL/NOAEL:
developmental) Rat (2-year feed) 10 mg kg1 d1
Rabbit (teratogenicity, gavage) 100 mg kg1 d1 Dog (2-year feed) 1.0 mg kg1 d1
(maternal) Mouse (78-week feed) 75 mg kg1 d1
150 mg kg1 d1 Rat (2-generation feed) 5 mg kg1 d1
(developmental) (parental)
Rat (2-year feed) ca. 2.5 mg kg1 d1 Rat (2-generation feed)) 50 mg kg1 d1
Dog (1-year feed) ca. 1 mg kg1 d1 (developmental)
Mouse (18-month feed) 26 mg kg1 d1 Rat (teratogenicity, gavage) 125 mg kg1 d1
ADI 0.0025 mg kg1 d1 (maternal and
RfD 0.01 mg kg1 d1 developmental)

Ecological [13, 109, 110]:

Ecological [111]:
LD50 (bobwhite quail, oral) 1536 mg/kg
LC50 (rainbow trout, 96-h) 1.8 mg/L LD50 (mallard duck, oral) >10 000 mg/kg
EC50 (daphnia magna, 48-h) 10 mg/L LC50 (rainbow trout, 96-h) 3.34 mg/L
EC50 (algae, 72-h) 0.966 mg/L LD50 (honeybee) 43.5 mg/bee
LD50 (honeybee, contact) 16 mg/bee
LC50 (earthworm, 14-d) 386.8 mg/kg soil

Dimethachlor [50563-36-5]
Butachlor [23184-66-9] Mammalian [1, 2, 113, 114]:
Mammalian [13, 462, 470]:
LD50 (rat, oral) 1600 to > 2000 mg/kg
LD50 (rat, oral) 26203050 mg/kg
LD50 (rat, dermal) > 3170 mg/kg
LD50 (mouse, oral) 41405030 mg/kg
LC50 (rat, 4-h inhalation) > 4.45 mg/L air
LD50 (rabbit, oral) > 5010 mg/kg
Rabbit: slightly irritating
LD50 (rabbit, dermal) 13 100 mg/kg
to skin and eyes
LC50 (rat, 4-h inhalation) > 5.34 mg/L air
NOEL/NOAEL:
Rabbit: moderately
Dog (90-day feed) 10.4 mg kg1 d1
irritating to skin
Rat (2-year feed) 12 mg kg1 d1
Rabbit: non to slightly
Mouse (18-month feed) 31.8 mg kg1 d1
irritating to eyes
ADI 0.12 mg kg1 d1
Guinea pig: a skin sensitizer
ARfD 0.5 mg kg1 d1
NOEL/NOAEL:
AOEL 0.1 mg kg1 d1
Rat (2-year feed) ca. 100 mg kg1 d1
Dog (1-year feed) 5 mg kg1 d1
ADI 0.05 mg kg1 d1

Ecological [114]:
Ecological [13]:
LD50 Japanese quail, oral) 524 mg/kg
LD50 (mallard duck, oral) >4640 mg/kg LC50 (rainbow trout, 96-h) 3.9 mg/L
LC50 (bluegill sunfish, 96-h) 0.44 mg/L EC50 (daphnia magna, 48-h) 24 mg/L
EC50 (daphnia magna, 48-h) 2.4 mg/L EC50 (algae, 72-h) 0.054 mg/L
EC50 (algae, 72-h) 0.2 mg/L LD50 (honeybee, contact) 200 mg/bee
LD50 (honeybee, contact) >100 mg/bee LC50 (earthworm, 14-d) 70 mg/kg soil
310 Weed Control, 2. Individual Herbicides Vol. 39

Metazachlor [67129-08-2] Ecological [13, 5]:

Mammalian [1, 2, 116, 117]:
LD50 (mallard duck, oral) 2510 mg/kg
LC50 (rainbow trout, 96-h) 1.23 mg/L
LD50 (rat, oral) 2150 mg/kg EC50 (daphnia magna, 48-h) 1.4 mg/L
LD50 (rat, dermal) > 6810 mg/kg EC50 (algae, 72-h) 0.008 mg/L
LC50 (rat, 4-h inhalation) > 34.5 mg/L air LD50 (honeybee, oral) >85 mg/bee
Rabbit: irritating LC50 (earthworm, 14-d) 570 mg/kg soil
to eyes and skin
Guinea pig: not
a skin sensitizer
NOEL/NOAEL: Pretilachlor [51218-49-6]
Rat (2-year feed) 3.6 mg kg1 d1
Mouse (18-month feed) 19 mg kg1 d1
Mammalian [1, 2, 489]:
ADI 0.08 mg kg1 d1
ARfD 0.5 mg kg1 d1 LD50 (rat, oral) 22003600 mg/kg
AOEL 0.2 mg kg1 d1 LD50 (mouse, oral) 18002300 mg/kg
LD50 (rat, dermal) 3100 mg/kg
LD50 (rat, i.p.) 11201300 mg/kg
LC50 (rat, 4-h inhalation) > 2.8 mg/L air
Ecological [1, 2, 116, 117]: Rabbit: moderately
irritating to skin
Rabbit: slightly
irritating to eyes
LD50 (bobwhite quail, oral) 2000 mg/kg
Guinea pig: a skin sensitizer
LC50 (rainbow trout, 96-h) 8.5 mg/L
Nonmutagenic
EC50 (daphnia magna, 48-h) 33 mg/L
NOEL/NOAEL:
EC50 (algae, 72-h) 0.0162 mg/L
Rat (2-generation feed) ca. 200 mg kg1 d1
LD50 (honeybee, oral) 72.2 mg/bee
(developmental)
LC50 (earthworm, 14-d) 500 mg/kg soil
Rat (teratology, gavage) 300 mg kg1 d1
(maternal and
developmental)
Rat (2-year feed) 1.86 mg kg1 d1
S-Metolachlor [87392-12-9]/[17896-20-1] Dog (1-year feed) ca. 7.5 mg kg1 d1
Mammalian [13, 5, 19, 488]: Mouse (2-year feed) 24 mg kg1 d1
ADI 0.018 mg kg1 d1

LD50 (rat, oral) 12002780 mg/kg

LD50 (rat, dermal) > 3170 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg Ecological [1, 2]:
LC50 (rat, 4-h inhalation) 2.91 mg/L air
Rabbit: mildly irritating
LD50 (Japanese quail, oral) 10 000 mg/kg
to skin and eyes
LC50 (rainbow trout, 96-h) 0.9 mg/L
Guinea pig: a skin sensitizer
EC50 (daphnia magna, 48-h) 13 mg/L
Nonmutagenic
EC50 (algae, 72-h) 9.29 mg/L
NOEL/NOAEL:
LD50 (honeybee, contact) 93 mg/bee
Rat (2-generation feed) 7.85 mg kg1 d1
(parental,
developmental)
Rat (teratogenicity, 50 mg kg1 d1
gavage) (maternal) Propachlor [1918-16-7]
Rat (teratogenicity, >1000 mg kg1 d1 Mammalian [13, 122, 123, 490, 491]:
gavage) (developmental)
Rabbit (teratogenicity, 20 mg kg1 d1
gavage) (maternal) LD50 (rat, oral) 5501700 mg/kg
Rabbit (teratogenicity, >500 mg kg1 d1 1800 mg/kg
gavage) (developmental) LD50 (mouse, oral) 290306 mg/kg
Rat (2-year feed) 15.0 mg kg1 d1 LD50 (rabbit, dermal) > 20 000 mg/kg
Dog (1-year feed) 9.7 mg kg1 d1 LC50 (rat, 4-h inhalation) > 1.2 mg/L air
Mouse (84-week feed) 150 mg kg1 d1 Rabbit: slightly irritating to skin
ADI 0.1 mg kg1 d1 Rabbit: moderately to
ARfD 3.0 mg kg1 d1 severely irritating to eyes
AOEL 15 mg kg1 d1 Guinea pig: a skin sensitizer
Nonmutagenic
Vol. 39 Weed Control, 2. Individual Herbicides 311
NOEL/NOAEL:
Rat (2-generation feed) 3 mg kg1 d1
Ecological [13]:
(parental)
Rat (2-generation feed) 30 mg kg1 d1 LD50 (bobwhite quail, oral) 2000 mg/kg
(developmental) EC50 (daphnia magna, 48-h) 100 mg/L
Rat (teratogenicity, gavage) 200 mg kg1 d1 LD50 (honeybee) 100 mg/bee
Rabbit (teratogenicity, gavage) 5 mg kg1 d1 LC50 (earthworm, 14-d) 1000 mg/kg soil
Rat (2-year feed) ca. 2.6 mg kg1 d1
Dog (1-year feed) 9 mg kg1 d1
Mouse (18-month feed) 1.6 mg kg1 d1
ADI 0.02 mg kg1 d1
2.4. 1,3,5-Triazines

Ametryn [834-12-8]
Ecological [13, 122, 123, 490, 491]:
Mammalian [13, 128, 492]:

LD50 bobwhite quail, oral) 91 mg/kg LD50 (rat, oral) 14201810 mg/kg
LC50 (rainbow trout, 96-h) 0.17 mg/L LD50 (mouse, oral) 13701910 mg/kg
EC50 (daphnia magna, 48-h) 7.8 mg/L LD50 (rat, dermal) > 5000 mg/kg
EC50 (algae, 72-h) 0.015 mg/L LD50 (rabbit, dermal) > 2020 mg/kg
LD50 (honeybee, oral) 197 mg/bee LC50 (rat, 4-h inhalation) > 5.17 mg/L air
LC50 (earthworm, 14-d) 218 mg/kg soil Rabbit: non irritating
to skin and eyes
Guinea pig: not a skin
sensitizer
Propisochlor [86763-47-5] Nonmutagenic
Mammalian [1, 2]: NOEL/NOAEL:
Rat (2-generation feed) ca. 1.3 mg kg1 d1
Rat (teratogenicity, gavage) 5 mg kg1 d1
(maternal)
LD50 (rat, oral) 20883433 mg/kg > 250 mg kg1 d1
LD50 (rat, dermal) > 2000 mg/kg (developmental)
LC50 (rat, 4-h inhalation) >5 mg/L air Rabbit (teratogenicity, gavage) 10 mg kg1 d1
NOEL/NOAEL: (maternal)
1 1
Rat (90-day feed) 25 mg kg d > 60 mg kg1 d1
ADI: 2.5 mg kg1 d1 (developmental)
Rat (2-year feed) 2.0 mg kg1 d1
Dog (1-year feed) 7.2 mg kg1 d1
Mouse (18-month feed) 1.5 mg kg1 d1
Ecological [1, 2]: ADI 0.015 mg kg1 d1

LD50 (Japanese quail, oral) 688 mg/kg

LC50 (rainbow trout, 96-h) 0.25 mg/L Ecological [13, 128]:
EC50 (daphnia magna, 48-h) 6.19 mg/L
EC50 (algae, 72-h) 0.028 mg/L
LD50 (honeybee, oral) 100 mg/bee LD50 (mallard duck, oral) 5620 mg/kg
LC50 (rainbow trout, 96-h) 5 mg/L
EC50 (daphnia magna, 48-h) 28 mg/L
EC50 (algae, 72-h) 0.0036 mg/L
LD50 (honeybee, oral) 100 mg/bee
Thenylchlor [96491-05-3] LC50 (earthworm, 14-d) 166 mg/kg soil
Mammalian [13]:

LD50 (rat, oral) > 5000 mg/kg Atrazine [1912-24-9]

LD50 (mouse, oral) > 5000 mg/kg Mammalian [13, 131133, 440, 462, 493]:
LD50 (rat, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 5.67 mg/L air
NOEL/NOAEL: LD50 (rat, oral) 18693090 mg/kg
Rat (2-year feed) 6.84 mg kg1 d1 LD50 (mouse, oral) > 13323992 mg/kg
ADI 0.068 mg kg1 d1 LD50 (rat, dermal) > 3100 mg/kg
LC50 (rat, 4-h inhalation) > 5.8 mg/L air
312 Weed Control, 2. Individual Herbicides Vol. 39
Rabbit: nonirritating to
skin and eyes
Ecological [13, 5, 480]:
Guinea pig: a skin sensitizer
Human: not a contact LD50 (pheasant, oral) 400 mg/kg
sensitizer LC50 (rainbow trout, 96-h) 9 mg/L
Nonmutagenic EC50 (daphnia magna, 48-h) 49 mg/L
NOEL/NOAEL: EC50 (algae, 72-h) 0.2 mg/L
Rat (2-generation feed) ca. 3.3 mg kg1 d1 LD50 (honeybee, contact) 100 mg/bee
(parental) LC50 (earthworm, 14-d) 600 mg/kg soil
Rat (teratogenicity, gavage) 25 mg kg1 d1
(maternal)
Rabbit (teratogenicity, 1 mg kg1 d1
gavage) (maternal) Cyprazine [22936-86-3]
Rabbit (teratogenicity, gavage) 5 mg kg1 d1 Mammalian [3, 431]:
Rat (2-year feed) 0.53.5 mg kg1 d1
Dog (1-year feed) 3.75 mg kg1 d1
LD50 (rat, oral) 5161200 mg/kg
Mouse (18-month feed) 1.4 mg kg1 d1
LD50 (mouse, oral) 10561306 mg/kg
Mouse (21-month feed) 1.2-1.4 mg kg1 d1
LD50 (rat, dermal) 3000 mg/kg
ADI 0.02 mg kg1 d1
LD50 (rabbit, oral) 12007500 mg/kg
ARfD 0.1 mg kg1 d1
LD50 (rabbit, dermal) 7500 mg/kg
AOEL 0.01 mg kg1 d1

Ecological [3, 480]:

Ecological [13, 130132]:
LC50 (carp, 96-h) 1020 mg/L
LD50 (Japanese quail, oral) 4237 mg/kg
LC50 (rainbow trout, 96-h) 4.511 mg/L
EC50 (daphnia magna, 24-h) 87 mg/L Desmetryn [1014-69-3]
EC50 (algae, 72-h) 0.059 mg/L
LD50 (honeybee, oral) 100 mg/bee
Mammalian [13]:
LC50 (earthworm, 14-d) 78 mg/kg soil
LD50 (rat, oral) 1390 mg/kg
LD50 (mouse, oral) 1750 mg/kg
LD50 (rat, dermal) 2000 mg/kg
LC50 (rat, 1-h inhalation) > 1.56 mg/L air
Cyanazine [21725-46-2] Rabbit: nonirritating to skin and eyes
Mammalian [13, 5, 462, 494, 495]: Guinea pig: a potential skin sensitizer
NOEL/NOAEL:
Rat (90-day feed) 1.5 mg kg1 d1
LD50 (rat, oral) 182234 mg/kg Dog (90-day feed) 6.6 mg kg1 d1
LD50 (mouse, oral) 380 mg/kg ADI: 0.0075 mg kg1 d1
LD50 (rabbit, oral) 141 mg/kg
LD50 (rat, dermal) > 1200 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 2.46 mg/L air
Ecological [13]:
Rabbit: nonirritating to eyes
Rabbit: mildly irritating to skin LC50 (carp, 96-h) 10 mg/L
Guinea pig: a skin sensitizer EC50 (daphnia magna, 48-h) 45 mg/L
Mostly nonmutagenic EC50 (algae, 72-h) 0.025 mg/L
NOEL/NOAEL: LD50 (honeybee, contact) 101 mg/bee
Rat (2-generation feed) 7.5 mg kg1 d1 LC50 (earthworm, 14-d) 160 mg/kg soil
(parental)
Rat (2-generation feed) 3.75 mg kg1 d1
(developmental)
Rabbit (teratogenicity, gavage) 1 mg kg1 d1 Dimethametryn [22936-75-0]
(maternal and Mammalian [1, 2]:
developmental)
Rat (2-year feed) 0.25 mg kg1 d1
Dog (1-year feed) 0.7 mg kg1 d1 LD50 (rat, oral) 3000 mg/kg
Mouse (2-year feed) 1.5 mg kg1 d1 LD50 (rat, dermal) > 2150 mg/kg
ADI 0.0013 mg kg1 d1 LC50 (rat, 4-h inhalation) > 5.4 mg/L air
Rabbit: irritating to skin
Vol. 39 Weed Control, 2. Individual Herbicides 313
1 1
Rabbit: slightly irritating to eyes Rat (teratogenicity, gavage) 36 mg kg d
Guinea pig: a skin sensitizer (maternal)
NOEL/NOAEL: 120 mg kg1 d1
Rat (90-day feed) ca. 27 mg kg1 d1 (developmental)
Dog (90-day feed) ca. 29 mg kg1 d1 Rabbit (teratogenicity, gavage) 3.5 mg kg1 d1
Rat (2-year feed) ca. 1.25 mg kg1 d1 (maternal)
Mouse (23-month feed) ca. 4 mg kg1 d1 24.5 mg kg1 d1
ADI 0.01 mg kg1 d1 (developmental)
Rat (2-year feed) 1 mg kg1 d1
Dog (1-year feed) 5 mg kg1 d1
Mouse (21-month feed) 60 mg kg1 d1
Ecological [1, 2]: RfD 0.05 mg kg1 d1

LC50 (rainbow trout, 96-h) 5.0 mg/L

EC50 (daphnia magna, 48-h) 0.92 mg/L
LD50 (honeybee, oral) 100 mg/bee Ecological [13, 137]:

LD50 (mallard duck) 1605 mg/kg

Indaziflam [950782-86-2] New herbicide; LC50 (rainbow trout, 96-h) 12 mg/L
no public data are yet available. EC50 (daphnia magna, 48-h) 20 mg/L
EC50 (algae, 72-h) 0.4 mg/L
LD50 (honeybee, contact) 30 mg/bee
Methoprotryne [841-06-5]
Mammalian [2, 3, 422]:

LD50 (rat, oral) >5000 mg/kg

Prometryn [7287-19-6]
LD50 (rat, dermal) 150 mg/kg Mammalian [13, 462, 497]:
Rabbit: irritating to skin and eyes
Guinea pig: a skin sensitizer
NOEL/NOAEL: LD50 (rat, oral) >2000 mg/kg
Rat (90-day feed) 250 mg kg1 d1 LD50 (rat, dermal) > 3100 mg/kg
Dog (90-day feed) 375 mg kg1 d1 LD50 (rabbit, dermal) > 2020 mg/kg
LC50 (rat, 4-h inhalation) > 5.17 mg/L air
Rabbit: nonirritating to skin
Rabbit: slightly irritating to eyes
Ecological [2, 3, 480]: Guinea pig: not a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
LC50 (rainbow trout, 96-h) 8 mg/L Rat (2-generation feed) ca. 0.7 mg kg1 d1
LC50 (carp, 96-h) 31 mg/L Rat (teratogenicity, gavage) 50 mg kg1 d1
EC50 (daphnia magna, 48-h) 42 mg/L Rabbit (teratogenicity, gavage) 12 mg kg1 d1
(maternal)
Rabbit (teratogenicity, gavage) 72 mg kg1 d1
(developmental)
Prometon [1610-18-0] Rat (2-year feed) ca. 37.5 mg kg1 d1
Mammalian [13, 137, 462, 496]: Dog (2-year feed) 4 mg kg1 d1
Mouse (18-month feed) ca. 1.4 mg kg1 d1
ADI 0.01 mg kg1 d1
LD50 (rat, oral) 15184345 mg/kg
LD50 (mouse, oral) 2160 mg/kg
LD50 (rabbit, dermal) > 2020 mg/kg
LC50 (rat, 4-h inhalation) > 3.26 mg/L air
Rabbit: slightly to mildly Ecological [13]:
irritating to skin
Rabbit: mildly irritating to eyes
Guinea pig: not a skin sensitizer
LD50 (mallard duck, oral) 2150 mg/kg
Nonmutagenic
LC50 (rainbow trout, 96-h) 5.5 mg/L
NOEL/NOAEL:
EC50 (daphnia magna, 48-h) 12.7 mg/L
Rat (2-generation feed) 1 mg kg1 d1
EC50 (algae, 72-h) 0.002 mg/L
(parental)
LD50 (honeybee, contact) 99 mg/bee
Rat (2-generation feed) 7.5 mg kg1 d1
LC50 (earthworm, 14-d) 153 mg/kg soil
(developmental)
314 Weed Control, 2. Individual Herbicides Vol. 39

Propazine [139-40-2] Simetryn [1014-70-6]

Mammalian [13, 5, 138, 498]: Mammalian [1, 2, 499]:

LD50 (rat, oral) 3840 mg/kg

LD50 (rat, dermal) > 3100 mg/kg LD50 (rat, oral) 7501195 mg/kg
LD50 (rabbit, dermal) > 10 200 mg/kg LD50 (mouse, oral) 16001710 mg/kg
LC50 (rat, 4-h inhalation) > 2.04 mg/L air LD50 (rat, i.p.) 196236 mg/kg
Rabbit: mildly irritating LD50 (rat, dermal) > 3100 mg/kg
to skin and eyes LC50 (rat, 4-h inhalation) > 4.88 mg/L air
NOEL/NOAEL: Rabbit: slightly irritating to skin
Rat (90/130-day feed) 13 mg kg1 d1 Rabbit: nonirritating to eyes
Dog (90-day feed) 7 mg kg1 d1 Guinea pig: not a skin sensitizer
ADI 0.046 mg kg1 d1 Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) ca. 10 mg kg1 d1
(parental)
Ecological [13, 5, 138]: > 50 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) 3 mg kg1 d1
LD50 (mallard duck, oral) 10 000 mg/kg (maternal)
LC50 (rainbow trout, 96-h) 17.5 mg/L > 75 mg kg1 d1
EC50 (daphnia magna, 48-h) 11 mg/L (developmental)
EC50 (algae, 72-h) 0.18 mg/L Rabbit (teratogenicity, gavage) 15 mg kg1 d1
LD50 (honeybee, contact) 16 mg/bee (maternal)
60 mg kg1 d1
(developmental)
Rat (2-year feed) 1.15 mg kg1 d1
Simazine [122-34-9] Dog (2-year feed) 10.5 mg kg1 d1
Mammalian [13, 140, 141]: Mouse (2-year feed) 56 mg kg1 d1
ADI 0.025 mg kg1 d1

LD50 (rat, oral) > 5000 mg/kg

LD50 (mouse, oral) > 5000 mg/kg
LD50 (rabbit, oral) > 5000 mg/kg
LD50 (rat, dermal) > 2000 mg/kg
Ecological [1, 2]:
LD50 (rabbit, dermal) > 3100 mg/kg
LC50 (rat, 4-h inhalation) > 5.5 mg/L air
Rabbit: nonirritating to skin and eyes LD50 (mallard duck, oral) 4640 mg/kg
Guinea pig: not a skin sensitizer LC50 (rainbow trout, 96-h) 7 mg/L
Nonmutagenic EC50 (daphnia magna, 48-h) 50 mg/L
NOEL/NOAEL: EC50 (algae, 72-h) 0.0098 mg/L
ca. 0.7 mg kg1 d1
(parental)
Rat (2-generation feed) ca. 30 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) 10 mg kg1 d1 Terbumeton [33693-04-8]
Rabbit (teratogenicity, gavage) 5 mg kg1 d1 Mammalian [1, 2]:
Rat (2-year feed) 0.5 mg kg1 d1
Dog (1-year feed) 0.7 mg kg1 d1
Mouse (18-month feed) 5.7 mg kg1 d1
ADI/AOEL: 0.005 mg kg1 d1 LD50 (rat, oral) 651 mg/kg
LD50 (mouse, oral) 2343 mg/kg
LD50 (rat, dermal) > 3170 mg/kg
LC50 (rat, 4-h inhalation) > 10 mg/L air
Ecological [13, 140, 141]: Rat: irritating to skin
Rabbit: slightly irritating to eyes
Guinea pig: a skin sensitizer
LD50 (mallard duck, oral) 4640 mg/kg NOEL/NOAEL:
LC50 (bluegill sunfish, 96-h) 90 mg/L Dog (90-day feed) 25 mg kg1 d1
EC50 (daphnia magna, 48-h) 1.1 mg/L Rat (2-year feed) 7.5 mg kg1 d1
EC50 (algae, 72-h) 0.04 mg/L Mouse (18-month feed) 25 mg kg1 d1
LD50 (honeybee, contact) 97 mg/bee ADI: 0.075 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil
Vol. 39 Weed Control, 2. Individual Herbicides 315

Ecological [1, 2]: Ecological [13, 5]:

LD50 (mallard duck, oral) 4640 mg/kg

LC50 (rainbow trout, 96-h) 14 mg/L LC50 (rainbow trout, 96-h) 1.1 mg/L
EC50 (daphnia magna, 72-h) 40 mg/L EC50 (daphnia magna, 48-h) 2.66 mg/L
EC50 (algae, 72-h) 0.009 mg/L EC50 (algae, 72-h) 0.0024 mg/L
LD50 (honeybee) 100 mg/bee LD50 (honeybee, contact) 225 mg/bee
LC50 (earthworm, 14-d) 170 mg/kg soil

Terbuthylazine [5915-41-3]
Mammalian [13]: Triaziflam [131475-57-5]
Mammalian [144]:

LD50 (rat, oral) 1590 to > 2000 mg/kg

LD50 (rat, dermal) > 2000 mg/kg LD50 (rat, oral) >5000 mg/kg
LC50 (rat, 4-h inhalation) > 5.3 mg/L air LD50 (rat, dermal) >2000 mg/kg
Rabbit: irritating to skin and eyes Rabbit: nonirritating to skin and eyes
Guinea pig: not a skin sensitizer Guinea pig: not a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) 0.4 mg kg1 d1
Rat (lifetime feed) 0.22 mg kg1 d1 Ecological [144]:
Dog (1-year feed) 0.4 mg kg1 d1
Mouse (2-year feed) 15.4 mg kg1 d1
ADI/AOEL: 0.004 mg kg1 d1 EC50 (daphnia magna, 48-h) 11.2 mg/L
ARfD 0.008 mg kg1 d1

Trietazine [1912-26-1]
Ecological [13]: Mammalian [1, 2]:

LD50 (rat, oral) 494841 mg/kg

LD50 (rat, dermal) > 600 mg/kg
LD50 (mallard duck, oral) 395 mg/kg
Rabbit: irritating to skin and eyes
LC50 (rainbow trout, 96-h) 2.2 mg/L
Guinea pig: a skin sensitizer
EC50 (daphnia magna, 48-h) 21 mg/L
NOEL/NOAEL:
EC50 (algae, 72-h) 0.0128 mg/L
Rat (90-day feed) 0.8 mg kg1 d1
LD50 (honeybee, oral) >100 mg/bee
LC50 (earthworm, 14-d) 142 mg/kg soil

Ecological [1, 2]:

Terbutryn [886-50-0]
Mammalian [13, 5]: LD50 (pheasant, oral) 800 mg/kg
LC50 (fish, 96-h) 3.3 mg/L
EC50 (daphnia magna, 48-h) 21 mg/L
EC50 (algae, 72-h) 0.13 mg/L
LD50 (rat, oral) 2500 mg/kg
LD50 (honeybee) 50 mg/bee
LD50 (mouse, oral) 500 mg/kg
LD50 (rat, dermal) > 2000 mg/kg
LD50 (rabbit, dermal) > 20 000 mg/kg
LC50 (rat, 4-h inhalation) > 2.2 mg/L air
Rabbit: nonirritating to skin 2.5. Ureas
Rabbit: irritating to eyes
Guinea pig: not a skin sensitizer Chlorbromuron [13360-45-7]
NOEL/NOAEL:
Rat (2-year feed) ca. 15 mg 1
kg d 1 Mammalian [13]:
Dog (1-year feed) ca. 2.7 mg kg1 d1
Mouse (2-year feed) ca. 400 mg kg1 d1 LD50 (rat, oral) > 2150 mg/kg
ADI: 0.027 mg kg1 d1 LD50 (rat, dermal) > 2000 mg/kg
LD50 (rabbit, dermal) > 10 000 mg/kg
316 Weed Control, 2. Individual Herbicides Vol. 39
LC50 (rat, 6-h inhalation) > 1.05 mg/L air
Rabbit: irritating to skin and eyes
Ecological [13, 480]:
NOEL/NOAEL:
Rat (90-day feed) 21 mg kg1 d1 LD50 (mallard duck, oral) >2000 mg/kg
Dog (90-day feed) > 10.5 mg kg1 d1 LC50 rainbow trout, 96-h) >100 mg/L
EC50 (daphnia magna, 48-h) 2.95 mg/L
EC50 (algae, 72-h) 0.016 mg/L
LD50 (honeybee, contact) 16 mg/bee
Ecological [13, 480]:

Cumyluron [99485-76-4]
LC50 (rainbow trout, 96-h) 5 mg/L Mammalian [150, 503]:
EC50 (daphnia magna, 48-h) 5.8 mg/L
EC50 (algae, 72-h) 0.017 mg/L
LD50 (honeybee, contact) 16 mg/bee LD50 (rat, oral) 9612074 mg/kg
LD50 (rat, dermal) >2000 mg/kg
LD50 (mouse, oral) >5000 mg/kg
LC50 (rat, 4-h inhalation) >6.21 mg/L air
Rabbit: not a skin irritant
Chlorotoluron [15545-48-9] Rabbit: mild irritant to eyes
Mammalian [13, 500, 501]: Guinea pig: not a sensitizer
Nonmutagenic
NOEL/NOAEL:
LD50 (rat, oral) > 5000 mg/kg Dog (1-year gavage) 1 mg kg1 d1
LD50 (rat, dermal) > 2000 mg/kg Rat (2-year feed) 2.673.40 mg kg1 d1
LC50 (rat, 4-h inhalation) > 5.3 mg/L air Mouse (2-year feed) 14.417.1 mg kg1 d1
Rabbit: nonirritating to skin and eyes Rat (2-generation, feed) 40.3 mg kg1 d1
Guinea pig: not a skin sensitizer (parental and
NOEL/NOAEL: developmental)
Rat (2-year feed) 5 mg kg1 d1 Rabbit (teratogenicity, gavage) 300 mg kg1 d1
Mouse (2-year feed) 11.3 mg kg1 d1 (maternal)
ADI 0.04 mg kg1 d1 Rabbit (teratogenicity, gavage) 1000 mg kg1 d1
AOEL 0.215 mg kg1 d1 (developmental)
ADI 0.01 mg kg1 d1

Ecological [13, 500, 501]: Ecological [150]:

LD50 (Japanese quail, feeding) >5620 ppm

LD50 (Japanese quail) 272 mg/kg LC50 (carp, 96-h) 44 mg/L
LC50 (rainbow trout, 96-h) 20 mg/L EC50 (daphnia magna, 48-h) 69 mg/L
EC50 (daphnia magna, 48-h) 67 mg/L
EC50 (algae, 72-h) 0.024 mg/L
LD50 (honeybee, oral) 177 mg/bee
LC50 (earthworm, 14-d) 1000 mg/kg soil Cycluron [2163-69-1]
Mammalian [2, 3]:

LD50 (rat, oral) 1500 mg/kg

Chloroxuron [1982-47-4]
Mammalian [13, 502]:
Daimuron [42609-52-9]
LD50 (rat, oral) 37005400 mg/kg
LD50 (rat, dermal) > 3000 mg/kg
Mammalian [13]:
LD50 (rabbit, dermal) > 10 000 mg/kg
LC50 (rat, 4-h inhalation) > 1.35 mg/L air LD50 (rat, oral) > 5000 mg/kg
Rabbit: nonirritating to eyes LD50 (mouse, oral) > 5000 mg/kg
Rabbit: slightly irritating to skin LD50 (rat, dermal) > 2000 mg/kg
NOEL/NOAEL: LC50 (rat, 4-h inhalation) > 3.25 mg/L air
Rat (120-d feed) 30 mg kg1 d1 NOEL/NOAEL:
Dog (90-d feed) 16.7 mg kg1 d1 Rat (2-generation) > 500 mg kg1 d1
ADI 0.004 mg kg1 d1 Rat (90-day feed) 3.1 mg kg1 d1
Mouse (90-day feed) 6.6 mg kg1 d1
Vol. 39 Weed Control, 2. Individual Herbicides 317
1 1 1 1
Dog (1-year feed)  0.8 mg kg d ADI/AOEL 0.007 mg kg d
ADI: 0.3 mg kg1 d1 ARfD 0.016 mg kg1 d1
RfD 0.02 mg kg1 d1

Ecological [13]:
Ecological [13, 153, 504]:
LD50 (bobwhite quail, oral) >2000 mg/kg
LC50 (carp, 96-h) >40 mg/L LD50 (bobwhite quail, oral) 1104>2000 mg/kg
LC50 (rainbow trout, 96-h) 4.3 mg/L
EC50 (daphnia magna, 48-h) 5.7 mg/L
EC50 (algae, 72-h) 0.0027 mg/L
Dimefuron [34205-21-5] LD50 (honeybee, oral) 100 mg/bee
Mammalian [13]: LC50 (earthworm, 14-d) 798 mg/kg soil

LD50 (rat, oral) > 2000 mg/kg

LD50 (mouse, oral) > 10 000 mg/kg Fenuron [101-42-8]
LD50 (dog, oral) > 2000 mg/kg Mammalian [13]:
LD50 (rat, dermal) > 2000 mg/kg
Rabbit: nonirritating
LD50 (rat, oral) 64007500 mg/kg
to skin and eyes
Rabbit: nonirritating to skin
NOEL/NOAEL:
NOEL/NOAEL:
Dog (90-day feed) 20 mg kg1 d1
Rat (90-day feed) 25 mg kg1 d1
Rat (90-day feed) 150 mg kg1 d1
Rat (2-year feed) 15.5 mg kg1 d1
ADI 0.07 mg kg1 d1
Ecological [13]:

Ecological [13]: LD50 (mallard duck, oral) 5000 mg/kg

LC50 (rainbow trout, 96-h) 204 mg/L
EC50 (daphnia magna, 48-h) 502 mg/L
LD50 (bobwhite quail, oral) 3350 mg/kg
EC50 (algae, 72-h) 1.45 mg/L
LC50 (rainbow trout, 96-h) >1000 mg/L
EC50 (daphnia magna, 48-h) 575 mg/L
EC50 (algae, 72-h) 0.008 mg/L
LD50 (honeybee, contact) 500 mg/bee Fluometuron [2164-17-2]
LC50 (earthworm, 14-d) 300 mg/kg soil
Mammalian [13, 155]:

LD50 (rat, oral) 6416-8900 mg/kg

Diuron [330-54-1] LD50 (rat, dermal) > 2000 mg/kg
Mammalian [13, 153, 462, 504]: LD50 (rabbit, dermal) > 10 000 mg/kg
LC50 (rat, 4-h inhalation) 4.62 mg/L air
Rabbit: mildly irritating
LD50 (rat, oral) 4373400 mg/kg
to skin and eyes
LD50 (rabbit, dermal) > 2000 mg/kg
Guinea pig: possible
LC50 (rat, 4-h inhalation) >5 mg/L air
skin sensitizer
Rabbit: irritating to skin
Nonmutagenic
Rabbit: mildly irritating to eyes
NOEL/NOAEL:
Guinea pig: a skin sensitizer
Rat (2-generation feed) ca. 0.7 mg kg1 d1
Nonmutagenic
(parental)
NOEL/NOAEL:
Rat (teratogenicity, gavage) 10 mg kg1 d1
Rat (2-generation feed) ca. 15 mg kg1 d1
(maternal and
Rat (teratogenicity, gavage) 16 mg kg1 d1
developmental)
(maternal)
Rabbit (teratogenicity, gavage) 10 mg kg1 d1
80 mg kg1 d1
(maternal and
(developmental)
developmental)
Rabbit (teratogenicity, gavage) 10 mg kg1 d1
Rat (2-year feed) 19 mg kg1 d1
(maternal)
Dog (1-year feed) 10 mg kg1 d1
50 mg kg1 d1
Mouse (18-month feed) 1.3 mg kg1 d1
(developmental)
ADI 0.022 mg kg1 d1
Rat (2-year feed) ca. 12.5 mg kg1 d1
ARfD/AOEL 0.06 mg kg1 d1
Dog (2-year feed) ca. 4 mg kg1 d1
318 Weed Control, 2. Individual Herbicides Vol. 39
Rat (2-year feed) 7.26 mg kg d1
1
Ecological [13, 155]: Mouse (2-year feed) 3.42 mg kg1 d1
ADI 0.0342 mg kg1 d1
LD50 (mallard duck, oral) 2974 mg/kg
LC50 (rainbow trout, 96-h) 30 mg/L
EC50 (daphnia magna, 48-h) 54 mg/L
EC50 (algae, 72-h) 0.32 mg/L
Ecological [1, 2]:
LD50 (honeybee, oral) 34 mg/bee
LC50 (earthworm, 14-d) 1000 mg/kg soil LD50 (bobwhite quail, oral) > 2000 mg/kg
LC50 (rainbow trout, 96-h) 100140 mg/L
LD50 (honeybee, oral) 1600 mg/bee
Isoproturon [34123-59-6]
Mammalian [1, 2, 157]:
Linuron [330-55-2]
LD50 (rat, oral) 18262417 mg/kg
Mammalian [13, 161, 462]:
LD50 (mouse, oral) 3350 mg/kg
LD50 (rat, dermal) > 2000 mg/kg LD50 (rat, oral) 11961254 mg/kg
LC50 (rat, 4-h inhalation) > 1.95 mg/L air LD50 (rat, dermal) > 2000 mg/kg
Rabbit: irritating to skin and eyes LD50 (rabbit, dermal) > 5000 mg/kg
NOEL/NOAEL: LC50 (rat, 4-h inhalation) 0.85 mg/L air
Rat (90-day feed) 20 mg kg1 d1 Rabbit: mildly irritating
Dog (90-day feed) ca. 1.4 mg kg1 d1 to skin and eyes
Rat (2-year feed) ca. 4 mg kg1 d1 Guinea pig: not a skin sensitizer
ADI/AOEL 0.015 mg kg1 d1 Nonmutagenic
NOEL/NOAEL:
Rat (3-generation feed) ca. 1.7 mg kg1 d1
Rat (teratogenicity, feed) 12.1 mg kg1 d1
Ecological [1, 2, 157]: Rabbit (teratogenicity, gavage) 21 mg kg1 d1
(maternal)
LD50 (bird, oral) 400 mg/kg Rabbit (teratogenicity, gavage) 25 mg kg1 d1
LC50 (fish, 96-h) 18 mg/L (developmental)
EC50 (daphnia magna, 48-h) 0.58 mg/L Rat (2-year feed) 2.5 mg kg1 d1
EC50 (algae, 72-h) 0.013 mg/L Dog (2-year feed) 0.8 mg kg1 d1
LD50 (honeybee, oral) 195 mg/bee Mouse (2-year feed) ca. 21 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil ADI/ARfD 0.003 mg kg1 d1
AOEL 0.009 mg kg1 d1

Isouron [55861-78-4]
Mammalian [1, 2, 505]: Ecological [13, 160, 161]:

LD50 (bobwhite quail, oral) 314 mg/kg

LD50 (rat, oral) 630760 mg/kg
LC50 rainbow trout, 96-h) 16 mg/L
LD50 (mouse, oral) 520530 mg/kg
EC50 (daphnia magna, 24-h) 0.31 mg/L
LD50 (rat, dermal) > 5000 mg/kg
EC50 (algae, 72-h) 0.016 mg/L
LC50 (rat, 8-h inhalation) > 0.415 mg/L air
LD50 (honeybee, oral) 160 mg/bee
Rabbit: nonirritating to skin
LC50 (earthworm, 14-d) 1000 mg/kg soil
Rabbit: slightly irritating to eyes
Guinea pig: not a skin sensitizer
Nonmutagenic
NOEL/NOAEL: Methabenzthiazuron [18691-97-9]
Rat (2-generation feed) 20 mg kg1 d1
(parental and
Mammalian [1, 2]:
developmental)
Rat (teratogenicity, gavage) 20 mg kg1 d1 LD50 (rat, oral) > 5000 mg/kg
(maternal) LD50 (mouse, oral) > 2500 mg/kg
Rat (teratogenicity, gavage) 60 mg kg1 d1 LD50 (rabbit, oral) > 1000 mg/kg
(developmental) LD50 (dog, oral) > 1000 mg/kg
Rabbit (teratogenicity, gavage) 10 mg kg1 d1 LD50 (rat, dermal) > 5000 mg/kg
(maternal) LC50 (rat, 4-h inhalation) 5.12 mg/L air
Rabbit (teratogenicity, gavage) 100 mg kg1 d1 Rabbit: irritating to skin and eyes
(developmental) Guinea pig: a skin sensitizer
Vol. 39 Weed Control, 2. Individual Herbicides 319
NOEL/NOAEL:
Rat (2-year feed) 7.5 mg kg1 d1
Metoxuron [19937-59-8]
Dog (1-year feed) 5 mg kg1 d1 Mammalian [1, 2]:
Mouse (18-month feed) 21 mg kg1 d1
ADI: 0.05 mg kg1 d1
LD50 (rat, oral) 3200 mg/kg
LD50 (rat, dermal) > 2000 mg/kg
LC50 (rat, 2-week inhalation) >5 mg/L air
Ecological [1, 2]: NOEL/NOAEL:
Rat (90-day feed) 62.5 mg kg1 d1
Dog (90-day feed) 62.5 mg kg1 d1

LD50 (pheasant, oral) 1000 mg/kg

LC50 (rainbow trout, 96-h) 15.9 mg/L
EC50 (daphnia magna, 48-h) 30.6 mg/L Ecological [1, 2]:
EC50 (algae, 72-h) 0.033 mg/L
LD50 (honeybee, contact) 0.8 mg/bee
LC50 (rainbow trout, 96-h) 19 mg/L
LC50 (earthworm, 14-d) 840 mg/kg soil
EC50 (daphnia magna, 48-h) 216 mg/L
EC50 (algae, 72-h) 0.064 mg/L
LD50 (honeybee, contact) 16 mg/bee
LC50 (earthworm, 14-d) 1000 mg/kg soil
Metobenzuron [111578-32-6]
Mammalian [1]:
Monolinuron [1746-81-2]
Mammalian [13]:
LD50 (rat, oral) > 10 000 mg/kg
LD50 (mouse, oral) > 10 000 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg LD50 (rat, oral) 14302490 mg/kg
Rabbit: nonirritating to skin LD50 (rat, dermal) > 2000 mg/kg
Rabbit: slightly irritating to eyes LC50 (rat, 4-h inhalation) > 3.39 mg/L air
Nonmutagenic Rabbit: nonirritating to skin and eyes
Guinea pig: not a sensitizer
NOEL/NOAEL:
Rat (2-year feed) 0.5 mg kg1 d1
ADI: 0.005 mg kg1 d1
Metobromuron [3060-89-7]
Mammalian [13]:
Ecological [13]:
LD50 (rat, oral) 2603-10 000 mg/kg
LD50 (rat, dermal) > 3000 mg/kg LD50 (Japanese quail, oral) 1690 mg/kg
LD50 (rabbit, dermal) > 10 200 mg/kg LC50 (rainbow trout, 96-h) 42 mg/L
LC50 (rat, 4-h inhalation) > 1.1 mg/L air EC50 (daphnia magna, 48-h) 33 mg/L
Rabbit: irritating to skin and eyes EC50 (algae, 72-h) 0.001 mg/L
Guinea pig: a skin sensitizer LD50 (honeybee, oral) 296 mg/bee
NOEL/NOAEL: LC50 (earthworm, 14-d) 1000 mg/kg soil
Rat (3-generation feed) 5 mg kg1 d1
Rat (2-year feed) 17 mg kg1 d1
Dog (1-year feed) 3 mg kg1 d1
ADI 0.008 mg kg1 d1 Monuron [150-68-5]
Mammalian [2, 3]:

LD50 (rat, oral) 10533600 mg/kg

Ecological [13]:

LD50 (pheasant, oral) 565 mg/kg

Ecological [2, 3]:
LC50 (rainbow trout, 96-h) 45 mg/L
EC50 (daphnia magna, 48-h) 44 mg/L LD50 (mallard duck, oral) 5000 mg/kg
EC50 (algae, 72-h) 0.26 mg/L LC50 (bluegill sunfish, 96-h) 37 mg/L
LD50 (honeybee) >160 mg/bee EC50 (daphnia magna, 48-h) 11 mg/L
LC50 (earthworm, 14-d) 467 mg/kg soil LD50 (honeybee, contact) 110 mg/bee
320 Weed Control, 2. Individual Herbicides Vol. 39
Rabbit (teratogenicity, gavage) 25 mg kg1 d1
Neburon [555-37-3] Mouse (90-day feed) 83 mg kg1 d1
Mammalian [1, 2]: Rat (2-year feed) 50 mg kg1 d1
Dog (1-year feed) 25 mg kg1 d1
LD50 (rat, oral) > 11 000 mg/kg ADI: 0.07 mg kg1 d1
Rabbit: irritating to skin and eyes
Guinea pig: weak sensitizer

Ecological [13, 170]:

Ecological [1, 2]: LD50 (mallard duck, oral) 2500 mg/kg

LC50 (rainbow trout, 96-h) 87 mg/L
EC50 (daphnia magna, 48-h) 225 mg/L
EC50 (algae, 72-h) 0.05 mg/L
LC50 (fish, 96-h) 0.1 mg/L
LD50 (honeybee, contact) 30 mg/bee
EC50 (algae, 72-h) 0.015 mg/L

Thidiazuron [51707-55-2]
Siduron [1982-49-6] Mammalian [1, 2, 172]:
Mammalian [13, 167, 168, 462]:
LD50 (rat, dermal) 1000 mg/kg
LC50 (rat, 4-h inhalation) 2.3 mg/L air
LD50 (rat, oral) > 7500 mg/kg Rabbit: not an irritant
LD50 (rabbit, dermal) > 5500 mg/kg to skin and eyes
LC50 (rat, 4-h inhalation) > 5.8 mg/L air Guinea pig: not a sensitizer
Rabbit: irritating to skin and eyes Nonmutagenic
Guinea pig: a skin sensitizer NOEL/NOAEL:
NOEL/NOAEL: Rat (2-year feed) 811.3 mg kg1 d1
Rat (2-year feed) 25 mg kg1 d1 Mouse (2-year feed) 26.3-33.4 mg kg1 d1
Dog (2-year feed) ca. 63 mg kg1 d1 Dog (1-year feed) 2.5 mg kg1 d1
ADI 0.14 mg kg1 d1 Rat (3-generation feed) 10 mg kg1 d1
Rat (teratogenicity gavage) 4 mg kg1 d1
(maternal)
Rat (teratogenicity gavage) 38 mg kg1 d1
Ecological [13, 167, 168]: (developmental)
ADI 0.0038 mg kg1 d1

LD50 (bobwhite quail, oral) 10 000 mg/kg

LC50 (rainbow trout, 96-h) 14 mg/L
EC50 (daphnia magna, 48-h) 18 mg/L Ecological [1, 2, 172]:
EC50 (algae, 72-h) 0.25 mg/L
LD50 (honeybee, contact) 100 mg/bee
LD50 (pheasant, oral) 16 000 mg/kg
LC50 (rainbow trout, 96-h) 19 mg/L
EC50 (daphnia magna, 48-h) 10 mg/L
Tebuthiuron [34014-18-1] EC50 (algae, 72-h) 0.15 mg/L
LD50 (honeybee) 105 mg/bee
Mammalian [13, 170, 462, 466]:

LD50 (rat, oral) 644 mg/kg

LD50 (mouse, oral) 579 mg/kg
LD50 (rabbit, oral) 286 mg/kg
2.6. 2,6-Dinitroanilines
LD50 (dog, oral) > 500 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg Benfluralin [1861-40-1]
LC50 (rat, 4-h inhalation) 3.7 mg/L air Mammalian [13, 173, 174]:
Rabbit: non to slightly irritating
to skin and eyes
Guinea pig: not a skin sensitizer LD50 (rat, oral) > 10 000 mg/kg
Nonmutagenic LD50 (mouse, oral) > 5000 mg/kg
NOEL/NOAEL: LD50 (rabbit, oral) > 2000 mg/kg
Rat (2-generation feed) 20 mg kg1 d1 LD50 (dog, oral) > 2000 mg/kg
(parental) LD50 (rabbit, dermal) > 5000 mg/kg
Rat (teratogenicity, gavage) 80 mg kg1 d1 LC50 (rat, 4-h inhalation) > 2.16 mg/L air
Vol. 39 Weed Control, 2. Individual Herbicides 321
Rabbit: moderately irritating
to skin and eyes
Ecological [13]:
NOEL/NOAEL:
Dog (13-week capsules) 5 mg kg1 d1
Rat (2-year feed) 0.50.7 mg kg1 d1 LD50 (bobwhite quail, oral) 1200 mg/kg
Mouse (18-month feed) 6.5 mg kg1 d1 LC50 (rainbow trout, 96-h) 0.75 mg/L
ADI/AOEL 0.005 mg kg1 d1

Ethalfluralin [55283-68-6]
Ecological [13, 173, 174]: Mammalian [13, 178, 506]:

LD50 (rat, oral) 5350 mg/kg LD50 (rat, oral) > 5000 mg/kg
LD50 (bobwhite quail, oral) 2000 mg/kg LD50 (mouse, oral) > 10 000 mg/kg
LC50 (bluegill sunfish, 96-h) 6 mg/L LD50 (dog, oral) > 200 mg/kg
EC50 (daphnia magna, 48-h) 100 mg/L LD50 (rabbit, dermal) > 5000 mg/kg
EC50 (algae, 72-h) 100 mg/L LC50 (rat, 1-h inhalation) 2.8 mg/L air
LD50 (honeybee, contact) 100 mg/bee Rabbit: slightly to, severely
LC50 (earthworm, 14-d) 1000 mg/kg soil irritating to skin
Rabbit: slightly to moderately
irritating to eyes
Guinea pig: a skin sensitizer
Butralin [33629-47-9] NOEL/NOAEL:
Rat (2-generation feed) 37.5 mg kg1 d1
Mammalian [13]: (reproduction)
Rat (teratogenicity, gavage) 250 mg kg1 d1
LD50 (rat, oral) 10491170 mg/kg (maternal)
LD50 (rat, dermal) > 2000 mg/kg Rabbit (teratogenicity, gavage) 75 mg kg1 d1
LC50 (rat, 4-h inhalation) > 9.35 mg/L air (maternal and
Rabbit: slightly irritating to skin developmental)
Rabbit: moderately irritating to eyes Rat (2-year feed) 3.94.5 mg kg1 d1
Guinea pig: a skin sensitizer Dog (1-year feed) 4 mg kg1 d1
NOEL/NOAEL: Mouse (18-month feed) 10.3 mg kg1 d1
Rat (2-year feed) ca. 25 mg kg1 d1 ADI 0.042 mg kg1 d1
ADI/ARfD/AOEL 0.03 mg kg1 d1 AOEL 0.2 mg kg1 d1

Ecological [13, 178]:

Ecological [13]:
LD50 (bobwhite quail, oral) 2000 mg/kg
LD50 (bobwhite quail, oral) 2250 mg/kg LC50 (rainbow trout, 96-h) 0.14 mg/L
LC50 (rainbow trout, 96-h) 0.37 mg/L EC50 (daphnia magna, 48-h) 0.13 mg/L
EC50 (daphnia magna, 48-h) 0.12 mg/L EC50 (algae, 72-h) 0.009 mg/L
EC50 (algae, 72-h) 0.12 mg/L LD50 (honeybee, contact) 100 mg/bee
LD50 (honeybee, oral) 96 mg/bee LC50 (earthworm, 14-d) 1000 mg/kg soil
LC50 (earthworm, 14-d) 500 mg/kg soil

Fluchloralin [33245-39-5]
Dinitramine [29091-05-2] Mammalian [13, 471]:
Mammalian [13, 471]:
LD50 (rat, oral) 15501650 mg/kg
LD50 (rat, oral) 3000 mg/kg LD50 (mouse, oral) 730 mg/kg
LD50 (rabbit, dermal) > 6800 mg/kg LD50 (rabbit, oral) 8000 mg/kg
LC50 (rat, 4-h inhalation) > 0.16 mg/L air LD50 (dog, oral) 6400 mg/kg
Rabbit: mildly irritating to skin and eyes LD50 (rabbit, dermal) > 10 000 mg/kg
NOEL/NOAEL: LC50 (rat, 4-h inhalation) > 8.4 mg/L air
Rat (90-day feed) > 130 mg kg1 d1 Rabbit: mildly irritating
Dog (90-day feed) > 50 mg kg1 d1 to skin and eyes
Rat (2-year feed) 15 mg kg1 d1 NOEL/NOAEL:
ADI 0.1 mg kg1 d1 Rat (2-year feed) 220 mg kg1 d1
Dog (90-day feed) > 20 mg kg1 d1
322 Weed Control, 2. Individual Herbicides Vol. 39
1 1
Mouse (2-year feed) 660 mg kg d LC50 (rainbow trout, 96-h) 22 mg/L
Rat (2-generation feed) >500 mg kg1 d1 EC50 (daphnia magna, 48-h) 0.002 mg/L
(parental and
developmental)
ADI 0.0030.03 mg kg1 d1
Oryzalin [19044-88-3]
Mammalian [13, 181, 462]:
Ecological [13, 480]:
LD50 (rat, oral) > 5000 mg/kg
LD50 (mouse, oral) > 5000 mg/kg
LD50 (mallard duck, oral) 1300 mg/kg LD50 (dog, oral) > 1000 mg/kg
LC50 (rainbow trout, 96-h) 0.012 mg/L LD50 (rabbit, dermal) > 2000 mg/kg
EC50 (daphnia magna, 48-h) 0.56 mg/L LC50 (rat, 4-h inhalation) 1.03.17 mg/L air
LD50 (honeybee, contact) 90 mg/bee Rabbit: irritating [ to skin and eyes
Guinea pig: not a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
Isopropalin [33820-53-0] Rat (3-generation feed) 112.5 mg kg1 d1
Mammalian [2, 3, 466]: (parental)
Rat (3-generation feed) 178.5 mg kg1 d1
(developmental)
LD50 (rat, oral) >5000 mg/kg
Rat (teratogenicity, gavage) 50 mg kg1 d1
LD50 (dog, oral) >5000 mg/kg
(maternal,
LD50 (chicken, oral) >5000 mg/kg
developmental)
LD50 (rabbit, dermal) >2000 mg/kg
Rabbit (teratogenicity, gavage) 025 mg kg1 d1
NOEL/NOAEL:
1 1 (maternal)
Rat (90-day feed) 15 mg kg d
Rabbit (teratogenicity, gavage) 125 mg kg1 d1
Dog (90-day feed) 56.25 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) <123 mg kg1 d1
Dog (1-year feed) 5 mg kg1 d1
(maternal)
Rat (2-year feed) 15 mg kg1 d1
Rat (teratogenicity, gavage) 123 mg kg1 d1
Mouse (2-year feed) 75 mg kg1 d1
(developmental)
ADI/ARfD/AOE 0.015 mg kg1 d1
Rabbit (teratogenicity, gavage) 60 mg kg1 d1
0.12 mg kg1 d1
(maternal)
Rabbit (teratogenicity, gavage) 270 mg kg1 d1
(developmental)
RfD 0.015 mg kg1 d1 Ecological [13, 181]:

LD50 (mallard duck, oral) 135 mg/kg

Ecological [2, 3, 480]: LC50 (rainbow trout, 96-h) 3.26 mg/L
EC50 (daphnia magna, 48-h) 1.02 mg/L
EC50 (algae, 72-h) 18.1 mg/L
LD50 (bobwhite quail, oral) 2000 mg/kg
LD50 (honeybee, oral) 32 mg/bee
LC50 (rainbow trout, 96-h) 0.8 mg/L
LC50 (earthworm, 14-d) 1000 mg/kg soil
EC50 (daphnia magna, 48-h) 0.022 mg/L

Nitralin [4726-14-1] Pendimethalin [40487-42-1]

Mammalian [2, 3, 471]: Mammalian [13, 183, 184, 462]:

LD50 (rat, oral) 3189 mg/kg

LD50 (rat, oral) 2000 mg/kg
LD50 (mouse, oral) > 12 000 mg/kg
LD50 (rat, dermal) 2000 mg/kg
LD50 (rabbit, oral) > 5000 mg/kg
NOEL/NOAEL:
LD50 (dog, oral) > 5000 mg/kg
Rat (2-year feed) 100 mg kg1 d1
LD50 (rat, dermal) > 2500 mg/kg
Dog (2-year feed) 50 mg kg1 d1
LD50 (rabbit, dermal) > 5000 mg/kg
ADI 0.24 mg kg1 d1
LC50 (rat, 4-h inhalation) 320 mg/L air
Rabbit: irritating to skin and eyes
Guinea pig: a skin sensitizer
Ecological [2, 3, 480]: Nonmutagenic
NOEL/NOAEL:
Rat (3-generation feed) 41.5 mg kg1 d1
LD50 (mallard duck, oral) >2000 mg/kg (parental)
Vol. 39 Weed Control, 2. Individual Herbicides 323
1 1
Rat (teratogenicity, gavage) 500 mg kg d EC50 (algae, 72-h) 0.003 mg/L
(maternal) LD50 (honeybee, contact) 100 mg/bee
Rabbit (teratogenicity, gavage) 30 mg kg1 d1
(maternal)
Rabbit (teratogenicity, gavage) 60 mg kg1 d1
(developmental) Profluralin [26399-36-0]
Rat (2-year feed) 4.3 mg kg1 d1 Mammalian [3, 507]:
Dog (1-year capsule) 12.5 mg kg1 d1
Mouse (18-month feed) 75 mg kg1 d1
ADI 0.125 mg kg1 d1 LD50 (rat, oral) ca. 10 000 mg/kg
AOEL 0.234 mg kg1 d1 LD50 (rat, dermal) >3170 mg/kg
RfD 0.04 mg kg1 d1 LD50 (rabbit, dermal) 3969 mg/kg
LC50 (rat, 4-h inhalation) >3.0 mg/L air
Rabbit: minimally irritating to skin
Rabbit: moderately irritating to eyes
Ecological [13, 181]: NOEL/NOAEL:
Rat (90-d feed) 13 mg kg1 d1
Dog (90-d feed) 20 mg kg1 d1
LD50 (mallard duck, oral) 1421 mg/kg
LC50 (rainbow trout, 96-h) 0.138 mg/L
EC50 (daphnia magna, 48-h) 0.28 mg/L
EC50 (algae, 72-h) 0.006 mg/L Ecological [3, 480, 507]:
LD50 (honeybee, contact) 100 mg/bee
LC50 (earthworm, 14-d) 1000 mg/kg soil
LD50 (bobwhite quail, oral) >1000 mg/kg
LC50 (rainbow trout, 96-h) 0.015 mg/L
EC50 (algae, 72-h) >10 mg/L
Prodiamine [29091-21-2] LD50 (honeybee) toxic
Mammalian [1, 2, 462, 471]:

LD50 (rat, oral) > 5000 mg/kg Trifluralin [1582-09-8]

LD50 (mouse, oral) > 5000 mg/kg Mammalian [13, 187, 188, 462]:
LD50 (rat, dermal) > 2000 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 0.256 mg/L air LD50 (rat, oral) 1930- 5000 mg/kg
Rabbit: nonirritating to skin LD50 (mouse, oral) > 5000 mg/kg
Rabbit: mildly irritating to eyes LD50 (dog, oral) > 2000 mg/kg
Guinea pig: not a skin sensitizer LD50 (rabbit, dermal) > 5000 mg/kg
Nonmutagenic LC50 (rat, 1-h inhalation) 1.252 mg/L air
NOEL/NOAEL: Rabbit: nonirritating to skin
Rat (2-generation feed) ca. 13 mg kg1 d1 Rabbit: slightly irritating to eyes
(parental) Guinea pig: a skin sensitizer
Rat (teratogenicity, gavage) 300 mg kg1 d1 Nonmutagenic
(maternal) NOEL/NOAEL:
Rat (teratogenicity, gavage) 100 mg kg1 d1 Rat (2-generation feed) > 130 mg kg1 d1
(developmental) (reproduction)
Rabbit (teratogenicity, gavage) 100 mg kg1 d1 Rat (teratogenicity, gavage) 1000 mg kg1 d1
(maternal) Rabbit (teratogenicity, gavage) 1000 mg kg1 d1
Rabbit (teratogenicity, gavage) 500 mg kg1 d1 Rat (2-year feed) ca. 2.5 mg kg1 d1
(developmental) Dog (3-year feed) 10 mg kg1 d1
Rat (2-year feed) 7.2 mg kg1 d1 Mouse (2-year feed) 73 mg kg1 d1
Rat (2-year feed) 10 mg kg1 d1 ADI 0.015 mg kg1 d1
Dog (1-year feed) 20 mg kg1 d1 AOEL 0.026 mg kg1 d1
Dog (1-year feed) ca. 5.7 mg kg1 d1
Mouse (2-year feed) 6070 mg kg1 d1
ADI 0.05 mg kg1 d1
Ecological [13, 187, 188]:

LD50 (bobwhite quail, oral) 2250 mg/kg

Ecological [1, 2]: LC50 (rainbow trout, 96-h) 0.088 mg/L
EC50 (daphnia magna, 48-h) 0.245 mg/L
LD50 (Japanese quail, oral) 2250 mg/kg EC50 (algae, 72-h) 0.022 mg/L
LC50 (rainbow trout, 96-h) 0.83 mg/L LD50 (honeybee, contact) 100 mg/bee
EC50 (daphnia magna, 48-h) 0.66 mg/L LC50 (earthworm, 14-d) 1000 mg/kg soil
324 Weed Control, 2. Individual Herbicides Vol. 39
ADI 9 mg kg d1
1
2.7. Imidazolinones AOEL 14 mg kg1 d1

Imazamethabenz-methyl [81405-85-8]
Mammalian [13, 190, 462]:
Ecological [13, 192]:

LD50 (rat, oral) > 5000 mg/kg LD50 (bobwhite quail, oral) 1846 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg LC50 (salmon, 96-h) 122 mg/L
LC50 (rat, 4-h inhalation) > 5.8 mg/L air EC50 (daphnia magna, 48-h) 122 mg/L
Rabbit: nonirritating to skin EC50 (algae, 72-h) 0.037 mg/L
Rabbit: mildly irritating to eyes LD50 (honeybee, oral) 40 mg/bee
Guinea pig: a skin sensitizer LC50 (earthworm, 14-d) 901 mg/kg soil
NOEL/NOAEL:
Rat (2-generation feed) 93.2 mg kg1 d1
Rat (teratogenicity, gavage) < 250 mg kg1 d1
(maternal) Imazapic [104098-48-4]
Rat (teratogenicity, gavage) 250 mg kg1 d1 Mammalian[1, 2, 508]:
(developmental)
Rabbit (teratogenicity, gavage) 750 mg kg1 d1
(maternal) LD50 (rat, oral) > 5000 mg/kg
Rabbit (teratogenicity, gavage) 250 mg kg1 d1 LD50 (rabbit, dermal) > 2000 mg/kg
(developmental) LC50 (rat, 4-h inhalation) >2.38 mg/L air
Rat (2-year feed) 12.5 mg kg1 d1 Rabbit: slightly irritating to skin
Dog (1-year feed) 6.25 mg kg1 d1 Rabbit: moderately irritating to eyes
Mouse (18-month feed) 19.5 mg kg1 d1 Guinea pig: not a skin sensitizer
ADI: 0.0625 mg kg1 d1 Nonmutagenic
NOEL/NOAEL:
Rat (teratogenicity, gavage) 1000 mg kg1 d1
(maternal and
developmental)
Ecological [13]: Rabbit (teratogenicity, gavage) 350 mg kg1 d1
(maternal)
500 mg kg1 d1
LD50 (mallard duck, oral) 2150 mg/kg (developmental)
LC50 (rainbow trout, 96-h) 100 mg/L Rat (90-day feed) 1625 mg kg1 d1
EC50 (daphnia magna, 48-h) 220 mg/L ADI: 0.50 mg kg1 d1
EC50 (algae, 72-h) 78 mg/L
LD50 (honeybee, oral) 100 mg/bee
LC50 (earthworm, 14-d) 123 mg/kg soil
Ecological [1, 2]:

LD50 (mallard duck, oral) 2150 mg/kg

Imazamox [114311-32-9] LC50 (rainbow trout, 96-h) 100 mg/L
Mammalian [13, 192, 461]: EC50 (daphnia magna, 48-h) 100 mg/L
EC50 (algae, 72-h) 0.051 mg/L
LD50 (honeybee, contact) 100 mg/bee
LD50 (rat, oral) > 5000 mg/kg
LD50 (mouse, oral) > 4000 mg/kg
LC50 (rat, 4-h inhalation) > 6.3 mg/L air
Rabbit: irritating to Imazapyr [81334-34-1]
skin and eyes Mammalian [13, 194, 462]:
Nonmutagenic
NOEL/NOAEL:
Dog (1-year feed) 11561174 mg kg1 d1 LD50 (rat, oral) > 5000 mg/kg
Rat (2-year feed) 10681284 mg kg1 d1 LD50 (mouse, oral) > 2000 mg/kg
Mouse (18-month feed) 10531348 mg kg1 d1 LD50 (rabbit, oral) 4800 mg/kg
Rabbit (teratogenicity, gavage) 300 mg kg1 d1 LD50 (rat, dermal) > 2000 mg/kg
(maternal) LD50 (rabbit, dermal) > 2000 mg/kg
Rabbit (teratogenicity, gavage) 900 mg kg1 d1 LC50 (rat, 4-h inhalation) 5.1 mg/L air
(developmental) Rabbit: mildly irritating to skin
Rat (2-generation feed) 1639 mg kg1 d1 Rabbit: mildly to severely
(parental and irritating to eyes
developmental) Guinea pig: not a skin sensitizer
Vol. 39 Weed Control, 2. Individual Herbicides 325
Nonmutagenic
NOEL/NOAEL:
Imazethapyr [81335-77-5]
Rat (2-generation feed) 500 mg kg1 d1 Mammalian [13, 462]:
Rat (teratogenicity, gavage) 300 mg kg1 d1
(maternal)
Rat (teratogenicity, gavage) > 1000 mg kg1 d1 LD50 (rat, oral) > 5000 mg/kg
(developmental) LD50 (mouse, oral) > 5000 mg/kg
Rabbit (teratogenicity, gavage) > 400 mg kg1 d1 LD50 (rabbit, dermal) > 2000 mg/kg
(developmental) LC50 (rat, 4-h inhalation) 3.27 mg/L air
Rat (2-year feed) 500 mg kg1 d1 Rabbit: slightly to mildly
Dog (1-year feed) 250 mg kg1 d1 irritating to skin
Mouse (18-month feed) 1500 mg kg1 d1 Rabbit: slightly
RfD 2.5 mg kg1 d1 irritating to eyes
Guinea pig: a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
Ecological [13, 194]: Rat (3-generation feed) 500 mg kg1 d1
Rat (teratogenicity, gavage) > 1125 mg kg1 d1
(maternal)
LD50 (mallard duck, oral) 2150 mg/kg Rat (teratogenicity, gavage) 375 mg kg1 d1
LC50 (rainbow trout, 96-h) 100 mg/L (developmental)
EC50 (daphnia magna, 48-h) 100 mg/L Rabbit (teratogenicity, gavage) 300 mg kg1 d1
EC50 (algae, 72-h) 71 mg/L (maternal)
LD50 (honeybee, oral) 25 mg/bee Rabbit (teratogenicity, gavage) > 1000 mg kg1 d1
LC50 (earthworm, 14-d) 133 mg/kg soil (developmental)
Rat (2-year feed) 500 mg kg1 d1
Dog (1-year feed) 25 mg kg1 d1
Mouse (18-month feed) 750 mg kg1 d1
Imazaquin [81335-37-7] ADI 0.44 mg kg1 d1
Mammalian [13, 196, 462]:

LD50 (rat, oral) > 5000 mg/kg

LD50 (mouse, oral) 2363 mg/kg
Ecological [13]:
LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 5.7 mg/L air
Rabbit: mildly irritating to skin LD50 (mallard duck, oral) 2150 mg/kg
Rabbit: nonirritating to eyes LC50 (rainbow trout, 96-h) 340 mg/L
Guinea pig: not a skin sensitizer EC50 (daphnia magna, 48-h) 1000 mg/L
Nonmutagenic EC50 (algae, 72-h) 71 mg/L
NOEL/NOAEL: LD50 (honeybee, contact) 0.1 mg/bee
Rat (3-generation feed) 6501000 mg kg1 d1 LC50 (earthworm, 14-d) 10 000 mg/kg soil
Rat (teratogenicity, gavage) 500 mg kg1 d1
Rabbit (teratogenicity, gavage) 250 mg kg1 d1
(maternal)
500 mg kg1 d1
(developmental)
Rat (2-year feed) 250 mg kg1 d1
2.8. Phenoxy Compounds
500 mg kg1 d1
Dog (1-year feed) 25 mg kg1 d1 Bromofenoxim [13181-17-4]
Mouse (18-month feed) 150 mg kg1 d1 Mammalian [1, 2, 509]:
ADI/AOEL 0.25 mg kg1 d1

LD50 (rat, oral) 1217 mg/kg

LD50 (mouse, oral) 940 mg/kg
LD50 (dog, oral) >1000 mg/kg
Ecological [13]: LD50 (rat, dermal) >3000 mg/kg
LD50 (rabbit, dermal) >5000 mg/kg
LD50 (mallard duck, oral) 2150 mg/kg LC50 (rat, 6-h inhalation) >0.242 mg/L air
LC50 (rainbow trout, 96-h) 100 mg/L NOEL/NOAEL:
EC50 (daphnia magna, 48-h) 100 mg/L Mouse (90-day feed) 0.63 mg kg1 d1
EC50 (algae, 72-h) 21.5 mg/L Dog (90-day feed) 3 mg kg1 d1
LD50 (honeybee, oral) 6.5 mg/bee Rat (2-year feed) 3.8 mg kg1 d1
LC50 (earthworm, 14-d) 23.5 mg/kg soil ADI 0.0013 mg kg1 d1
326 Weed Control, 2. Individual Herbicides Vol. 39
NOEL/NOAEL:
Ecological [1, 2, 480]: Rat (2-year feed) 0.62 mg kg1 d1
ADI 0.0062 mg kg1 d1

LD50 (mallard duck, oral) >2250 mg/kg

LC50 (rainbow trout, 96-h) 0.18 mg/L
EC50 (daphnia magna, 48-h) 1.2 mg/L
Ecological [1]:
EC50 (algae, 72-h) 2.2 mg/L
LC50 (earthworm, 14-d) 1300 mg/kg soil LC50 (carp, 96-h) 369 mg/L
EC50 (daphnia magna, 48-h) 496 mg/L
EC50 (algae, 72-h) 246 mg/L

Clodinafop-propargyl [105512-06-9]
Mammalian [13, 197199]:
Cloprop [101-10-0]
Mammalian [13]:
LD50 (rat, oral) 234-2271 mg/kg
LD50 (rat, dermal) 2000 mg/kg
LC50 (rabbit, dermal) >2000 mg/kg LD50 (rat, oral) 3360 mg/kg
LC50 (rat, 4-h inhalation) 2.32 mg/L air LD50 (rabbit, dermal) >2000 mg/kg
Rabbit: nonirritating to skin and eyes Rabbit: skin and eye irritant
Guinea pig: a sensitizer Guinea pig: a skin sensitizer
Nonmutagenic NOEL/NOAEL:
NOEL/NOAEL: Mouse (1.88-year feed) 900 mg kg1 d1
Rat (2-year feed) 0.032 1
mg kg d 1 Rat (2-year feed) 400 mg kg1 d1
Rat (2-generation feed) 4.63 mg kg1 d1 ADI 0.5 mg kg1 d1
(parental)
Rat (2-generation feed) 89 mg kg1 d1
(developmental) Ecological [13]:
Mouse (78-week feed) 1.1 mg kg1 d1
Dog (1-year feed) 3.38 mg kg1 d1
Rat (teratogenicity, gavage) 160 mg kg1 d1 LD50 (mallard duck, oral) 5620 mg/kg
(maternal) LC50 (rainbow trout, 96-h) 21 mg/L
Rat (teratogenicity, gavage) 5 mg kg1 d1
(developmental)
ADI 0.003 mg kg1 d1 Cyhalofop-butyl [122008-85-9]
AOEL 0.026 mg kg1 d1
RfD 0.0003 mg kg1 d1
Mammalian [2, 3, 202, 203, 461, 510]:
ARfD 0.05 mg kg1 d1
LD50 (rat, oral) >5000 mg/kg
LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) >5.63 mg/L air
Ecological [13, 198]: Nonmuatagenic
NOEL/NOAEL:
Rat (2-year feed) 0.823-2.475 mg kg1 d1
LD50 (bobwhite quail, oral) 1363 mg/kg
Dog (1-year feed) >46.7 mg kg1 d1
LC50 (bluegill sunfish, 96-h) 0.21 mg/L
Mouse (78-week feed) 0.99 mg kg1 d1
EC50 (daphnia magna, 48-h 0.77 mg/L
Rat (2-generation feed) 4.85 mg kg1 d1
EC50 (algae, 72-h) 1.6 mg/L
(parental)
LD50 (honeybee, oral) 17.8 mg/bee
Rat (2-generation feed) 55.1 mg kg1 d1
LC50 (earthworm, 14-d) 197 mg/kg soil
(developmental)
ADI 0.003 mg kg1 d1
AOEL 0.03 mg kg1 d1
Clomeprop [84496-56-0] RfD 0.01 mg kg1 d1

Mammalian [1, 200]:

Ecological [2, 3, 202, 203]:
LD50 (rat, oral) 3250 to > 5000 mg/kg
LD50 (mouse, oral) > 5000 mg/kg
LD50 (bobwhite quail, oral) 2250 mg/kg
LD50 (rat, dermal) > 5000 mg/kg
LC50 (rainbow trout, 96-h) 100 mg/L
LD50 (mouse, dermal) > 5000 mg/kg
EC50 (daphnia magna, 48-h) 100 mg/L
LC50 (rat, 4-h inhalation) > 1.5 mg/L air
EC50 (algae, 72-h) 100 mg/L
Rabbit: slightly irritating to skin
LD50 (honeybee, oral) 40 mg/bee
Rabbit: moderately irritating to eyes
LC50 (earthworm, 14-d) 1000 mg/kg soil
Guinea pig: not a sensitizer
Vol. 39 Weed Control, 2. Individual Herbicides 327

2,4-D acid [94-75-7] Ecological [13, 5, 209]:

Mammalian [13, 5, 204207, 511]:
LD50 (bobwhite quail, oral) 1545 mg/kg
LC50 (rainbow trout, 96-h) 3.5 mg/L
LD50 (rat, oral) 443699 mg/kg EC50 (daphnia magna, 48-h) 25 mg/L
LD50 (mouse, oral) 138 mg/kg EC50 (algae, 72-h) 1.1 mg/L
LD50 (rat, dermal) > 1600 mg/kg LD50 (honeybee, oral) 100 mg/bee
LD50 (rabbit, dermal) > 2000 mg/kg LC50 (earthworm, 14-d) 1000 mg/kg soil
LC50 (rat, 4-h inhalation) 1.79 mg/L air
Rabbit: irritating to skin
Rabbit: severely irritating to eyes
Guinea pig: a skin sensitizer
Nonmutagenic Dichlorprop [7547-66-2]
NOEL/NOAEL: Mammalian [13, 461, 462, 495]:
Rat (neurotoxicity, acute 75 mg kg1 d1
and 1-year feed)
Rat (2-generation feed) 5 mg kg1 d1 LD50 (rat, oral) 8251470 mg/kg
(parental and LD50 (mouse, oral) 400 mg/kg
developmental) LD50 (rat, dermal) > 4000 mg/kg
Rat (teratogenicity, gavage) 25 mg kg1 d1 LD50 (mouse, dermal) 1400 mg/kg
(maternal and LC50 (rat, 4-h inhalation) > 0.65 mg/L air
developmental) Rabbit: irritating to skin and eyes
Rabbit (teratogenicity, gavage) 30 mg kg1 d1 Guinea pig: not a skin sensitizer
(maternal) Nonmutagenic
Rabbit (teratogenicity, gavage) > 90 mg kg1 d1 NOEL/NOAEL:
(developmental) Rat (90-day feed) 5 mg kg1 d1
Rat (2-year feed) 1 mg kg1 d1 Rat (2-year feed) 3.6 mg kg1 d1
Dog (1-year feed) 1 mg kg1 d1 ADI 0.06 mg kg1 d1
Mouse (2-year feed) 5 mg kg1 d1 ARfD 0.5 mg kg1 d1
ADI 0.05 mg kg1 d1
AOEL 0.15 mg kg1 d1

Ecological [13]:
Ecological [13, 5, 204207]:
LD50 (Japanese quail, oral) 504 mg/kg
LC50 (rainbow trout, 96-h) 5.22 mg/L
LD50 (bobwhite quail, oral) 500 mg/kg EC50 (daphnia magna, 48-h) 5.4 mg/L
LC50 (fathead minnow, 96-h) 100 mg/L EC50 (algae, 96-h) 222 mg/L
EC50 (daphnia magna, 48-h) 100 mg/L LD50 (honeybee, contact) 16 mg/bee
EC50 (algae, 72-h) 24 mg/L LC50 (earthworm, 14-d) 1000 mg/kg soil
LD50 (honeybee, oral) 94 mg/bee
LC50 (earthworm, 14-d) 350 mg/kg soil

Dichlorprop-P [15165-67-0]
2,4-DB [94-82-6] Mammalian [13, 215217]:
Mammalian [13, 5, 209, 210, 462, 471]:
LD50 (rat, oral) 825470 mg/kg
LD50 (rat, oral) 7001960 mg/kg LD50 (rat, dermal) > 4000 mg/kg
LD50 (rat, dermal) >2000 mg/kg LC50 (rat, 4-h inhalation) > 7.4 mg/L air
LC50 (rat, 4-h inhalation) 2.3 mg/L air Rabbit: skin and eye irritant
Rabbit: nonirritating Nonmutagenic
to skin and eyes NOEL/NOAEL:
Guinea pig: not a sensitizer Rat (2-year feed) 5 mg kg1 d1
Nonmutagenic Dog (1-year feed) 3 mg kg1 d1
NOEL/NOAEL: Mouse (78-week feed) 6 mg kg1 d1
Dog (90-day feed) 8 mg kg1 d1 Rat (2-gneration feed) 7.8 mg kg1 d1
Rat (2-year feed) 3 mg kg1 d1 Rat (2-gneration feed) 39 mg kg1 d1
ADI: 0.021 mg kg1 d1 ADI 0.06 mg kg1 d1
ARfD 0.004 mg kg1 d1 ARfD 0.5 mg kg1 d1
AOEL 0.08 mg kg1 d1 AOEL 0.35 mg kg1 d1
328 Weed Control, 2. Individual Herbicides Vol. 39

Ecological [13, 217]: Fenoxaprop-ethyl [66441-23-4]

Mammalian [13, 495, 512]:
LD50 (bobwhite quail, oral) 279 mg/kg
LC50 (rainbow trout, 96-h) 109 mg/L
LD50 (rat, oral) 2357 mg/kg
EC50 (daphnia magna, 48-h) 100 mg/L
LD50 (mouse, oral) 46705490 mg/kg
EC50 (algae, 72-h) 67 mg/L
LD50 (rat, dermal) >2000 mg/kg
LD50 (honeybee, oral) 200 mg/bee
LC50 (rat, 4-h inhalation) 0.51 mg/L air
LC50 (earthworm, 14-d) 1000 mg/kg soil
Rabbit: skin irritant
Rabbit: nonirritating to eyes
Nonmutagenic
NOEL/NOAEL:
Diclofop-methyl [51338-27-3] Rat (2-year feed) 1.582.0 mg kg1 d1
Mammalian [13, 219]: Dog (2-year capsules) 0.91.1 mg kg1 d1
Mouse (2-year feed) 6 mg kg1 d1
Rat (2-generation feed) 1.5 mg kg1 d1
LD50 (rat, oral) 563580 mg/kg (parental and
LD50 (rat, dermal) 5000 mg/kg developmental)
LC50 (rat, 4-h inhalation) 1.36 mg/L air Rat (teratogenicity, gavage) 32 mg kg1 d1
Rabbit: not a skin irritant (maternal and
Rabbit: irritating to eyes developmental)
Guinea pig: a sensitizer RfD 0.0025 mg kg1 d1
NOEL/NOAEL: ARfD 0.32 mg kg1 d1
1 1
Rat (2-year feed) 0.23 mg kg d
Dog (15-month feed) 0.2 mg kg1 d1
Mouse (102-week feed) 0.24-0.95 mg kg1 d1
Rat (2-generation feed) 1.5 mg kg1 d1
(parental and
Ecological [13]:
developmental)
Rabbit (teratogenicity, gavage) 0.3 mg kg1 d1
LD50 (mallard duck, oral) 2510 mg/kg
(maternal)
LC50 (salmon, 96-h) 0.48 mg/L
Rabbit (teratogenicity, gavage) 3 mg kg1 d1
EC50 (daphnia magna, 48-h) 11.5 mg/L
(developmental)
EC50 (algae, 72-h) 0.43 mg/L
ADI 0.001 mg kg1 d1
LD50 (honeybee, contact) 300 mg/bee
AOEL 0.003 mg kg1 d1
LC50 (earthworm, 14-d) 413 mg/kg soil
RfD 0.003 mg kg1 d1
ARfD 0.1 mg kg1 d1

Fenoxaprop-P-ethyl [113158-40-0]
Ecological [13]: Mammalian [1, 2, 221, 222, 495, 513]:

LD50 (rat, oral) 3150 mg/kg

LD50 (Japanese quail, oral) 15 000 mg/kg
LD50 (rat, dermal) >2000 mg/kg
LC50 (bluegill sunfish, 96-h) 0.24 mg/L
LC50 (rat, 4-h inhalation) 1.22 mg/L air
EC50 (daphnia magna, 48-h) 0.23 mg/L
Rabbit: skin and eye irritant
EC50 (algae, 72-h) 1.5 mg/L
Guinea pig: a skin sensitizer
LD50 (honeybee, contact) 100 mg/bee
Nonmutagenic
LC50 (earthworm, 14-d) 1000 mg/kg soil
NOEL/NOAEL:
Dog (1-year feed) 75 mg kg1 d1
Mouse (18-month feed) 750 mg kg1 d1
Rat (2-year feed) 0.7 mg kg1 d1
Disul-sodium [136-78-7] ADI 0.01 mg kg1 d1
Mammalian [3]: ARfD 0.1 mg kg1 d1
AOEL 0.014 mg kg1 d1

LD50 (rat, oral) 1500 mg/kg

LD50 (mouse, oral) 730 mg/kg
Rabbit: skin irritant Ecological [1, 2, 221, 222, 480, 513]:
NOEL/NOAEL:
ADI 0.004 mg kg1 d1
LD50 (Japanese quail, oral) 2000 mg/kg
LC50 (bluegill sunfish, 96-h) 0.19 mg/L
Vol. 39 Weed Control, 2. Individual Herbicides 329
EC50 (daphnia magna, 48-h) 1.06 mg/L
EC50 (algae, 72-h) 0.54 mg/L
Ecological [1, 2, 516]:
LD50 (honeybee, oral) 0.199 mg/bee
LC50 (earthworm, 14-d) 500 mg/kg soil
LD50 (mallard duck, oral) 3960 mg/kg
LC50 (rainbow trout, 96-h) 1.31 mg/L
EC50 (daphnia magna, 48-h) 1.0 mg/L
Fluazifop-butyl [69806-50-4] EC50 (algae, 72-h) 1.8 mg/L
LD50 (honeybee, contact) 200 mg/bee
Mammalian [13, 514, 515]: LC50 (earthworm, 14-d) 1000 mg/kg soil

LD50 (rat, oral) 3030 mg/kg

LD50 (rabbit, oral) 621 mg/kg
LD50 (rabbit, dermal) 2420 mg/kg
Haloxyfop [69806-34-4]
LC50 (rat, 4-h inhalation) 5.2 mg/L air Mammalian [1, 2, 466, 517]:
Rabbit: a skin and eye irritant
Guinea pig: a skin sensitizer
LD50 (rat, oral) 337518 mg/kg
NOEL/NOAEL:
LD50 (rat, dermal) 5000 mg/kg
Dog (one-year, capsules) 5 mg kg1 d1
Rabbit: a skin and eye irritant
Rat (90-day feed) 50 mg kg1 d1
Nonmutagenic
Mouse (2-year feed) 0.65 mg kg1 d1
NOEL/NOAEL:
Rat (2-generation feed) 0.74 mg kg1 d1
Dog (1-year feed) 0.5 mg kg1 d1
(parental)
Mouse (2-year feed) 0.03 mg kg1 d1
Rat (2-generation feed) 4 mg kg1 d1
Rat (2-year feed) 0.065 mg kg1 d1
(developmental)
Rat (2-generation feed) 1 mg kg1 d1
Rat (teratogenicity gavage) 10 mg kg1 d1
(parental)
(maternal)
Rat (2-generation feed) 0.065 mg kg1 d1
Rat (teratogenicity gavage) 1 mg kg1 d1
(developmental)
(developmental)
Rat (teratogenicity, gavage) 1 mg kg1 d1
RfD 0.0074 mg kg1 d1
(maternal and
ARfD 0.50 mg kg1 d1
developmental)
ADI 0.0007 mg kg1 d1
ARfD 0.08 mg kg1 d1
AOEL 0.005 mg kg1 d1
Ecological [13]:

LD50 (mallard duck, oral) 17 000 mg/kg Ecological [1, 2]:

LC50 (rainbow trout, 96-h) 1.37 mg/L
EC50 (daphnia magna, 48-h) 316 mg/L
LD50 (honeybee, contact) 63 mg/bee LD50 (mallard duck, oral) >2150 mg/kg
LC50 (rainbow trout, 96-h) 800 mg/L
EC50 (daphnia magna, 48-h) 96.4 mg/L
EC50 (algae, 92-h) 106.5 mg/L

Fluazifop-P-butyl [79241-46-6]
Mammalian [1, 2, 223, 495, 516]:
Haloxyfop-P [95977-29-0]
Mammalian [1, 2, 224, 225, 517]:
LD50 (rat, oral) 2000 mg/kg
LD50 (rat, dermal) 2110 mg/kg LD50 (rat, oral) 330623 mg/kg
LC50 (rat, 4-h inhalation) 5.24 mg/L air LD50 (rat, dermal) >2000 mg/kg
Rabbit: a skin and eye irritant Rabbit: irritating to eyes
NOEL/NOAEL: Rabbit: not a skin irritant
Rat (2-year feed) 0.5 mg kg1 d1 Guinea pig: possibly a sensitizer
Dog (55-week capsules) 5 mg kg1 d1 Nonmutagenic
Rat (teratogenicity, gavage) 50 mg kg1 d1 NOEL/NOAEL:
(maternal) Rat (16-week feed) 0.065 mg kg1 d1
Rat (teratogenicity, gavage) 1 mg kg1 d1 Dog (1-year feed) 0.2 mg kg1 d1
(developmental) ADI 0.00065 mg kg1 d1
ADI 0.01 mg kg1 d1 ARfD 0.075 mg kg1 d1
ARfD/AOEL 0.02 mg kg1 d1 AOEL 0.05 mg kg1 d1
330 Weed Control, 2. Individual Herbicides Vol. 39

Ecological [1, 2, 224, 225]: Ecological [1, 2]:

LD50 (mallard duck, oral) >2150 mg/kg LD50 (bobwhite quail, oral 400 mg/kg
LC50 (rainbow trout, 96-h) 1.8 mg/L LC50 (rainbow trout, 96-h) 0.044 mg/L
EC50 (daphnia magna, 48-h) 6.2 mg/L EC50 (daphnia magna, 48-h) 0.58 mg/L
LD50 (honeybee, oral) >100 mg/bee EC50 (algae, 72-h) 2.3 mg/L
LC50 (earthworm, 14-d) >1000 mg/kg soil LD50 (honeybee, oral) 100 mg/bee
LC50 (earthworm, 14-d) 140.5 mg/kg soil

MCPA [94-74-6]
Mammalian [13, 226, 227, 461, 462, 471]: MCPB [94-81-5]
Mammalian [13, 230, 231]:
LD50 (rat, oral) 7001160 mg/kg
LD50 (mouse, oral) 800 mg/kg LD50 (rat, oral) 4700 mg/kg
LD50 (rat, dermal) > 4000 mg/kg LD50 (rat, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 6.36 mg/L air LC50 (rat, 4-h inhalation) > 1.14 mg/L air
Rabbit: irritating to eyes Rabbit: nonirritating to skin
NOEL/NOAEL: Rabbit: irritating to eyes
Rat (2-year feed) 4.4 mg kg1 d1 Guinea pig: a skin sensitizer
Mouse (2-year feed) ca. 18 mg kg1 d1 NOEL/NOAEL:
Rat (2-generation feed) 150 mg kg1 d1 Rat (90-day feed) ca. 6 mg kg1 d1
(parental and ADI 0.01 mg kg1 d1
developmental) ARfD 0.05 mg kg1 d1
ADI 0.05 mg kg1 d1 AOEL 0.06 mg kg1 d1
RfD 0.0044 mg kg1 d1
ARfD 0.05 mg kg1 d1
AOEL 0.04 mg kg1 d1

Ecological [13, 230, 231, 518]:

Ecological [13, 226, 227]: LD50 (bobwhite quail, oral) 282 mg/kg
LC50 (rainbow trout, 96-h) 4.3 mg/L
EC50 (daphnia magna, 48-h) 55 mg/L
LD50 (bobwhite quail, oral) 270 mg/kg
EC50 (algae, 72-h) 41 mg/L
LC50 (rainbow trout, 96-h) 50 mg/L
LD50 (honeybee, oral) 82 mg/bee
EC50 (daphnia magna, 48-h) 190 mg/L
LC50 (earthworm, 14-d) 252 mg/kg soil
EC50 (algae, 72-h) 80 mg/L
LD50 (honeybee, oral) 200 mg/bee
LC50 (earthworm, 14-d) 325 mg/kg soil

Mecoprop [7085-19-0]
Mammalian [13, 233, 234, 462]:
MCPA-thioethyl [25319-90-8]
Mammalian [1, 2]:
LD50 (rat, oral) 9301166 mg/kg
LD50 (mouse, oral) 650 mg/kg
LD50 (rat, oral) 450877 mg/kg LD50 (rat, dermal) > 4000 mg/kg
LD50 (mouse, oral) 749811 mg/kg LD50 (rabbit, dermal) 900 mg/kg
LD50 (mouse, dermal) > 1500 mg/kg LC50 (rat, 4-h inhalation) > 12.5 mg/L air
LC50 (rat, 4-h inhalation) > 0.044 mg/L air Rabbit: irritating to skin
Rabbit: irritating to skin and eyes Rabbit: highly irritating to eyes
Guinea pig: a skin sensitizer Guinea pig: a skin sensitizer
Nonmutagenic NOEL/NOAEL:
NOEL/NOAEL: Rat (90-day feed) 4.5 mg kg1 d1
Rat (2-year feed) 5 mg kg1 d1 Dog (90-day feed) 4 mg kg1 d1
Mouse (18-month feed) 3 mg kg1 d1 Rat (2-year feed) 1.1 mg kg1 d1
ADI 0.013 mg kg1 d1 ADI 0.01 mg kg1 d1
ARfD 0.15 mg kg1 d1 AOEL 0.04 mg kg1 d1
AOEL 0.04 mg kg1 d1 RfD 0.001 mg kg1 d1
Vol. 39 Weed Control, 2. Individual Herbicides 331

Ecological [13, 233, 234]: Propaquizafop [111479-05-1]

Mammalian [1, 2, 239]:
LD50 (bobwhite quail, oral) 700 mg/kg
LD50 (mallard duck, oral) 500 mg/kg
LD50 (rat, oral) > 5000 mg/kg
LC50 (fish, 96-h) 240 mg/L
LD50 (mouse, oral) 3009 mg/kg
EC50 (daphnia magna, 48-h) 200 mg/L
LD50 (rat, dermal) > 2000 mg/kg
EC50 (algae, 72-h) 237 mg/L
LC50 (rat, 4-h inhalation) > 2.5 mg/L air
LD50 (honeybee, oral) 100 mg/bee
Rabbit: nonirritating to skin
LC50 (earthworm, 14-d) 988 mg/kg soil
Rabbit: moderately irritating to eyes
Guinea pig: a potential skin sensitizer
NOEL/NOAEL:
Rat (2-year feed) 1.5 mg kg1 d1
Mecoprop-P [16484-77-8] Dog (1-year feed) 20 mg kg1 d1
Mammalian [1, 2, 235, 236]: Mouse (2-year feed) 1.5 mg kg1 d1
ADI 0.015 mg kg1 d1
AOEL 0.04 mg kg1 d1
LD50 (rat, oral) 4311050 mg/kg
LD50 (rat, dermal) > 4000 mg/kg
LC50 (rat, 4-h inhalation) > 5.6 mg/L air
Rabbit: irritating to skin and eyes Ecological [1, 2, 239]:
Guinea pig: a skin sensitizer
NOEL/NOAEL:
Rat (90-d feed) 4 mg kg1 d1 LD50 (bobwhite quail, oral) 2000 mg/kg
Rat (2-year feed) 1.1 mg kg1 d1 LC50 (carp, 96-h) 0.19 mg/L
Mouse (78-week feed) 20 mg kg1 d1 EC50 (daphnia magna, 48-h) 0.9 mg/L
ADI 0.01 mg kg1 d1 EC50 (algae, 72-h) 2.1 mg/L
AOEL 0.04 mg kg1 d1 LD50 (honeybee, oral) 20 mg/bee
LC50 (earthworm, 14-d) 500 mg/kg soil

Ecological [1, 2, 235, 236]:

Quizalofop-ethyl [76578-14-8]
LD50 (mallard duck, oral) 602 mg/kg Mammalian [13, 510, 519, 520]:
LC50 (fish, 96-h) 100 mg/L
EC50 (daphnia magna, 48-h) 91 mg/L
EC50 (algae, 72-h) 16 mg/L LD50 (rat, oral) 14601670 mg/kg
LD50 (honeybee, oral) 100 mg/bee LD50 (rat, dermal) 5000 mg/kg
LC50 (earthworm, 14-d) 988 mg/kg soil LC50 (rat, 4-h inhalation) 5.8 mg/L
Rabbit: irritating to skin and eyes
Guinea pig: a skin sensitizer
Nonmutagenic
Metamifop [256412-89-2] NOEL/NOAEL:
Mammalian [2, 238]: Mouse (78-week feed) 1.5 mg kg1 d1
Rat (2-year feed) 0.91.25 mg kg1 d1
Dog (1-year feed) 19 mg kg1 d1
LD50 (rat, oral) >2000 mg/kg
ADI 0.0090.01 mg kg1 d1
LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 2.61 mg/L air
Rabbit: not a skin irritant
Rabbit: possibly irritating to eyes

Ecological [13]:
Ecological [2]:
LD50 (mallard duck, oral) 2000 mg/kg
LC50 (bluegill sunfish, 96-h) 2.8 mg/L
LC50 (rainbow trout, 96-h) 0.307 mg/L
EC50 (daphnia magna, 48-h) 2.1 mg/L
EC50 (daphnia magna, 48-h) 0.288 mg/L
EC50 (algae, 72-h) 3.57 mg/L
EC50 (algae, 72-h) 2.03 mg/L
LD50 (honeybee, oral) 10 mg/bee
LD50 (honeybee, oral) 100 mg/bee
LC50 (earthworm, 14-d) 1000 mg/kg soil
LC50 (earthworm, 14-d) 1000 mg/kg soil
332 Weed Control, 2. Individual Herbicides Vol. 39
LC50 (rat, 4-h inhalation) 2.24 mg/L air
Quizalofop-P-ethyl [100646-51-3] Rabbit: slightly irritating to eyes
Mammalian [1, 2, 5, 241, 242, 521]: Rabbit: not a skin irritant
Guinea pig: not a sensitizer
Nonmutagenic
LD50 (rat, oral) 1182 mg/kg
NOEL/NOAEL:
LD50 (rat, dermal) 5000 mg/kg
Rabbit (teratogenicity, gavage) 5 mg kg1 d1
LC50 (rat, 4-h inhalation) 5.8 mg/L air
(maternal)
Rabbit: eye irritant
Rabbit (teratogenicity, gavage) 20 mg kg1 d1
Rabbit: nonirritating to skin
(developmental)
NOEL/NOAEL:
Rat (teratogenicity, gavage) 15 mg kg1 d1
Rat (2-year feed) 7.7 mg kg1 d1
(maternal and
ADI 0.009 mg kg1 d1
developmental)
AOEL 0.01 mg kg1 d1
Rat (2-generation feed) 6.47.3 mg kg1 d1
(parental)
Rat (2-generation feed) 73.284.0 mg kg1 d1
(developmental)
Ecological [1, 2, 241, 242]: Rat (2-year feed) 2.32.7 mg kg1 d1
Dog (1-year feed) 2.32.5 mg kg1 d1
Mouse (78-week feed) 244275 mg kg1 d1
LD50 (mallard duck, oral) 2000 mg/kg RfD 0.023 mg kg1 d1
LC50 (rainbow trout, 96-h) 0.48 mg/L ARfD 0.10 mg kg1 d1
EC50 (daphnia magna, 48-h) 0.29 mg/L
EC50 (algae, 72-h) 0.021 mg/L
LD (honeybee, contact) 100 mg/bee
LC (earthworm, 14-d) 500 mg/kg soil
Ecological [13]:

LD50 (mallard duck, oral) >2000 mg/kg

2,4,5-T [93-76-5] LC50 (rainbow trout, 96-h) 120 mg/L
Mammalian [13, 243, 522]: EC50 (daphnia magna, 48-h) 119 mg/L
LD50 (honeybee, oral) 24.8 mg/bee

LD50 (rat, oral) 500 mg/kg

LD50 (mouse, oral) 389 mg/kg
LD50 (dog, oral) >100 mg/kg
LD50 (rat, dermal) >5000 mg/kg Amitrole [61-82-5]
Rabbit: skin and eye irritant Mammalian [13, 5, 246248, 462]:
Guinea pig: skin sensitizer
NOEL/NOAEL:
Dog (90-d feed) 1.5 mg kg1 d1 LD50 (rat, oral) > 2500 mg/kg
Rat (2-year feed) 1.5 mg kg1 d1 LD50 (mouse, oral) > 5000 mg/kg
ADI 0.030.1 mg kg1 d1 LD50 (rat, dermal) > 2500 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 0.439 mg/L air
Rabbit: minimally
irritating to skin
Ecological [13, 243]: Rabbit: mildly irritating to eyes
Guinea pig: a potential
LD50 (mallard duck, oral) >2000 mg/kg skin sensitizer
LC50 (rainbow trout, 96-h) 1.3 mg/L Nonmutagenic
EC50 (daphnia magna, 48-h) 2.0 mg/L NOEL/NOAEL:
EC50 (algae, 72-h) 2.0 mg/L Rat (2-generation feed) 0.12 mg kg1 d1
(parental)
0.9 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) 100 mg kg1 d1
2.9. Triazoles (maternal and
developmental)
Amicarbazone [129909-90-6] Rabbit (teratogenicity, gavage) 5 mg kg1 d1
(maternal)
Mammalian [2, 3, 244, 523]:
20 mg kg1 d1
(developmental)
LD50 (rat, oral) 10152050 mg/kg Rat (2-year feed) 0.5 mg kg1 d1
LD50 (rat, dermal) >2000 mg/kg Dog (1-year feed) 0.29 mg kg1 d1
Vol. 39 Weed Control, 2. Individual Herbicides 333
1 1
Mouse (18-month feed) 1.5 mg kg d Nonmutagenic
Hamster (18-month feed) 1 mg kg1 d1 NOEL/NOAEL:
Rat (2-year inhalation) 0.5 mg kg1 d1 ADI 0.003 mg kg1 d1
ADI/AOEL 0.001 mg kg1 d1

Ecological [1, 2]:

Ecological [13, 5, 246248]:
LD50 (mallard duck, oral) >2000 mg/kg
LC50 (carp, 72-h) 1.2 mg/L
LD50 (bobwhite quail, oral) 2150 mg/kg EC50 (daphnia magna, 48-h) 500 mg/L
LC50 (salmon, 96-h) 1000 mg/L LD50 (honeybee, oral) >1000 mg/bee
EC50 (daphnia magna, 48-h) 6.1 mg/L
EC50 (algae, 72-h) 2.3 mg/L
LD50 (honeybee, contact) 100 mg/bee
LC50 (earthworm, 14-d) 448 mg/kg soil Carfentrazone-ethyl [128639-02-1]
Mammalian [2, 3, 253, 254]:

Azafenidin [68049-83-2] LD50 (rat, oral) >5000 mg/kg

LD50 (rat, dermal) >4000 mg/kg
Mammalian [1, 2, 471, 524]: LC50 (rat, 4-h inhalation) 5.09 mg/L air
Rabbit: minimally irritating to eyes
Rabbit: not a skin irritant
LD50 (rat, oral) > 5000 mg/kg Guinea pig: not a sensitizer
LD50 (rabbit, dermal) > 2000 mg/kg Nonmutagenic
LC50 (rat, 4-h inhalation) > 5.4 mg/L air NOEL/NOAEL:
Rabbit: slightly irritating to skin Dog (1-year feed) 50 mg kg1 d1
Rabbit: mild eye irritant Mouse (78-week feed) 1012 mg kg1 d1
Guinea pig: not a skin sensitizer Rat (2-year feed) 39 mg kg1 d1
Nonmutagenic Rat (teratogenicity, gavage) 100 mg kg1 d1
NOEL/NOAEL: (maternal)
Rat (2-year feed) 1.21-1.58 mg kg1 d1 Rat (teratogenicity, gavage) 600 mg kg1 d1
Dog (1-year feed) 0.30 mg kg1 d1 (developmental)
Mouse (18-month feed) 39.854.1 mg kg1 d1 Rabbit (teratogenicity, gavage) >150 mg kg1 d1
Rat (2-generation feed) 1.72.3 mg kg1 d1 (maternal)
(parental) Rabbit (teratogenicity, gavage) >300 mg kg1 d1
1.72.8 mg kg1 d1 (developmental)
(developmental) Rat (2-generation feed) 127142 mg kg1 d1
Rat (teratogenicity, gavage) 58 mg kg1 d1 (parental)
(maternal and Rat (2-generation feed) 387 mg/kg /d
developmental) (developmental)
Rabbit (teratogenicity, gavage) 12 mg kg1 d1 ADI 0.03 mg kg1 d1
(maternal) AOEL 0.6 mg kg1 d1
100 mg kg1 d1
(developmental)
RfD 0.003 mg kg1 d1
ADI 0.0004 mg kg1 d1 Ecological [2, 3, 253, 254]:

LD50 (bobwhite quail, oral) >2250 mg/kg

LC50 (rainbow trout, 96-h) 1.6 mg/L
Bencarbazone [173980-17-1] New herbi- EC50 (daphnia magna, 48-h) 9.8 mg/L
cicde; no toxicological data are yet available in EC50 (algae, 72-h) 0.012 mg/L
the public domain. LD50 (honeybee, oral) 200 mg/bee
LC50 (earthworm, 14-d) 820 mg/kg soil

Cafenstrole [125306-83-4]
Mammalian [1, 2]:
Cloransulam-methyl [147150-35-4]
Mammalian [13, 256]:
LD50 (rat, oral) > 5000 mg/kg
LD50 (mouse, oral) > 5000 mg/kg
LD50 (rat, dermal) > 2000 mg/kg LD50 (rat, oral) >5000 mg/kg
LC50 (rat, 4-h inhalation) > 1.97 mg/L air LD50 (rabbit, dermal) >2000 mg/kg
334 Weed Control, 2. Individual Herbicides Vol. 39
LC50 (rat, 4-h inhalation) 3.77 mg/L air
Rabbit: irritant to skin and eyes
Florasulam [145701-23-1]
Guinea pig: not a sensitizer Mammalian [259261]:
Nonmutagenic
NOEL/NOAEL: LD50 (rat, oral) >5000 mg/kg
Dog (1-year feed) 10 mg kg1 d1 LD50 (rabbit, dermal) >2000 mg/kg
Rat (2-year feed) 75 mg kg1 d1 LC50 (rat, 4-h inhalation) >5.0 mg/L air
Mouse (78-week feed) 10 mg kg1 d1 Rabbit: nonirritating to skin and eyes
Rat (2-generation feed) 10 mg kg1 d1 Guinea pig: not a sensitizer
(parental) Nonmutagenic
Rat (2-generation feed) 100 mg kg1 d1 NOEL/NOAEL:
(developmental) 250 mg kg1 d1
RfD 0.1 mg kg1 d1 (maternal)
Rat (teratogenicity, gavage) 750 mg kg1 d1
(developmental)
100 mg kg1 d1
Ecological [13, 256]: (maternal)
Rabbit (teratogenicity, gavage) 500 mg kg1 d1
(developmental)
LD50 (bobwhite quail, oral) 2250 mg/kg Mouse (78-week feed) 1000 mg kg1 d1
LC50 (rainbow trout, 96-h) 86 mg/L Rat (2-year feed) 10 mg kg1 d1
EC50 (daphnia magna, 48-h) 163 mg/L Dog (1-year feed) 5 mg kg1 d1
EC50 (algae, 72-h) 0.0035 mg/L ADI/AOEL/RfD 0.05 mg kg1 d1
LD50 (honeybee, contact) >25 mg/bee
LC50 (earthworm, 14-d) 859 mg/kg soil
Ecological [2, 259, 260]:

LD50 (bird, oral) 1046 mg/kg

Diclosulam [145701-21-9] LC50 (fish, 96-h) 100 mg/L
Mammalian [2, 525]: EC50 (daphnia magna, 48-h) 292 mg/L
EC50 (algae, 72-h) 0.0089 mg/L
LD50 (honeybee, oral) 100 mg/bee
LD50 (rat, oral) >5000 mg/kg
LC50 (earthworm, 14-d) 1320 mg/kg soil
LD50 (rabbit, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 5.04 mg/L air
Rabbit: very slightly irritating to eyes
Rabbit: not a skin irritant Flucarbazone-sodium [181274-17-9]
Guinea pig: not a sensitizer Mammalian [2, 262, 526]:
Nonmutagenic
NOEL/NOAEL:
Rabbit (teratogenicity, gavage) 65 mg kg1 d1 LD50 (rat, oral) >5000 mg/kg
(maternal) LD50 (rabbit, dermal) >5000 mg/kg
Rabbit (teratogenicity, gavage) 650 mg kg1 d1 LC50 (rat, 4-h inhalation) 5.13 mg/L air
(developmental) Rabbit: not a skin irritant
Rat (2-generation feed) 1000 mg kg1 d1 Rabbit: slightly irritating to eyes
(parental and Guinea pig: not a sensitizer
developmental) Nonmutagenic
Rat (2-year feed) 5 mg kg1 d1 NOEL/NOAEL:
Dog (1-year feed) 25 mg kg1 d1 Rat (2-year feed) 125 mg kg1 d1
Mouse (2-year feed) 50 mg kg1 d1 Dog (1-year feed) 35.937.1 mg kg1 d1
ADI/RfD 0.05 mg kg1 d1 Mouse (2-year feed) 275 mg kg1 d1
Rabbit (teratogenicity, gavage) 100 mg kg1 d1
(maternal)
Rabbit (teratogenicity, gavage) 300 mg kg1 d1
(developmental)
Ecological [2]: Rat (2-generation feed) 287340 mg kg1 d1
(parental and
developmental)
LD50 (bobwhite quail, oral) 2250 mg/kg
Rabbit (teratogenicity, gavage) 100 mg kg1 d1
LC50 (rainbow trout, 96-h) 110 mg/L
(maternal)
EC50 (daphnia magna, 48-h) 72 mg/L
Rabbit (teratogenicity, gavage) 300 mg kg1 d1
EC50 (algae, 72-h) 0.0016 mg/L
(developmental)
LD50 (honeybee, contact) 25 mg/bee
RfD 0.36 mg kg1 d1
LC50 (earthworm, 14-d) 991 mg/kg soil
ARfD 3.0 mg kg1 d1
Vol. 39 Weed Control, 2. Individual Herbicides 335

Ecological [2, 262]: Metosulam [139528-85-1]

Mammalian [1, 2]:
LD50 (bobwhite quail, oral) >2000 mg/kg
LC50 (rainbow trout, 96-h) 97 mg/L LD50 (rat, oral) > 5000 mg/kg
EC50 (daphnia magna, 48-h) 109 mg/L LD50 (mouse, oral) > 5000 mg/kg
EC50 (algae, 72-h) 6.4 mg/L LD50 (rabbit, dermal) > 2000 mg/kg
LD50 (honeybee) 200 mg/bee LC50 (rat, 4-h inhalation) > 1.9 mg/L air
LC50 (earthworm, 14-d) 1000 mg/kg soil Rabbit: nonirritating to skin and eyes
Guinea pig: not a skin sensitizer
NOEL/NOAEL
Rat (2-year feed) 5 mg kg1 d1
Mouse (18-month feed) 1000 mg kg1 d1
Flumetsulam [98967-40-9] ADI 0.05 mg kg1 d1
Mammalian [2, 263, 265]: ARfD 0.25 mg kg1 d1
AOEL 0.01 mg kg1 d1

LD50 (rat, oral) >5000 mg/kg

LD50 (rabbit, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 1.2 mg/L air Ecological [1, 2]:
Rabbit: irritating to skin and eyes
Nonmutagenic
NOEL/NOAEL LD50 mallard duck, oral) 2000 mg/kg
Rat (2-year feed) 500 mg kg1 d1 LC50 (rainbow trout, 96-h) 29.3 mg/L
Dog (1-year feed) 100 mg kg1 d1 EC50 (daphnia magna, 48-h) 100 mg/L
Mouse (78-week feed) >1000 mg kg1 d1 EC50 (algae, 72-h) 0.075 mg/L
Rabbit (teratogenicity, gavage) 100 mg kg1 d1 LD50 (honeybee, oral) 50 mg/bee
(maternal) LC50 (earthworm, 14-d) 1000 mg/kg soil
Rabbit (teratogenicity, gavage) >700 mg kg1 d1
(developmental)
RfD 1.0 mg kg1 d1
Penoxasulam [219714-96-2]
Mammalian [2, 268, 269, 527]:

Ecological [2, 264]: LD50 (rat, oral) >5000 mg/kg

LD50 (rabbit, dermal) >5000 mg/kg
LC50 (rat, 4-h inhalation) 3.5 mg/L air
LD50 (bobwhite quail, oral) 2250 mg/kg Rabbit: mild irritant to skin and eyes
LC50 (rainbow trout, 96-h) 293 mg/L Guinea pig: not a sensitizer
EC50 (daphnia magna, 48-h) 254 mg/L NOEL/NOAEL:
EC50 (algae, 72-h) 10.7 mg/L Rabbit (teratogenicity, gavage) 25 mg kg1 d1
LD50 (honeybee, contact) >100 mg/bee (maternal and
developmental)
Rat (teratogenicity, gavage) 500 mg kg1 d1
(maternal and
developmental)
Flupoxam [119126-15-7] Rat (2-generation feed) 30 mg kg1 d1
Mammalian [1, 2]: (parental)
Rat (2-generation feed) 100 mg kg1 d1
(developmental)
Dog (1-year feed) 14.7 mg kg1 d1
LD50 (rat, oral) > 5000 mg/kg
Mouse (78-week feed) 375 mg kg1 d1
LD50 (rabbit, dermal) > 2000 mg/kg
Rat (2-year feed) 50 mg kg1 d1
Rabbit: nonirritating to skin
ADI 0.05 mg kg1 d1
Rabbit: mildly irritating to eyes
RfD 0.147 mg kg1 d1
Nonmutagenic

Ecological [2, 268, 269]:

Ipfencarbazone [212201-70-2] New herbi-
cide, no toxicological data are available in the LD50 (bobwhite quail, oral) 2025 mg/kg
public domain. LC50 (rainbow trout, 96-h) >102 mg/L
336 Weed Control, 2. Individual Herbicides Vol. 39
EC50 (daphnia magna, 48-h) 98.3 mg/L Dog (1-year feed) 589619 mg kg d1
1

EC50 (algae, 72-h) 0.49 mg/L Rat (2-year feed) 1000 mg kg1 d1
LD50 (honeybee) >110 mg/bee Mouse (78-week feed) 100 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil ADI 1.0 mg kg1 d1

Propoxycarbazone-sodium [181274-15-7] Ecological [2, 529]:

Mammalian [2, 270, 528]:
LD50 (mallard duck, oral) 2000 mg/kg
LD50 (rat, oral) >5000 mg/kg LC50 (rainbow trout, 96-h) 87 mg/L
LD50 (rat, dermal) >5000 mg/kg EC50 (daphnia magna, 48-h) 100 mg/L
LC50 (rat, 4-h inhalation) 5.03 mg/L air EC50 (algae, 72-h) 0.135 mg/L
Rabbit: nonirritating LD50 (honeybee, contact) 100 mg/bee
to skin and eyes LC50 (earthworm, 14-d) 10 000 mg/kg soil
Nonmutagenic
NOEL/NOAEL:
Rat (2-year feed) 200 mg kg1 d1
Dog (1-year feed) 605 mg kg1 d1
Mouse (107-week feed) 369 mg kg1 d1
Sulfentrazone [122836-35-5]
Rat (2-generation feed) 50 mg kg1 d1 Mammalian [2, 3, 273, 274]:
(parental)
Rat (2-generation feed) 800 mg kg1 d1
LD50 (rat, oral) 2855 mg/kg
(developmental)
LD50 (rabbit, dermal) >2000 mg/kg
ADI 0.4 mg kg1 d1
LC50 (rat, 4-h inhalation) 4.14 mg/L air
AOEL 0.3 mg kg1 d1
Rabbit: mild eye irritant
RfD 0.748 mg kg1 d1
Rabbit: not a skin irritant
Guinea pig: not a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
Ecological [2]: Rat (teratogenicity, gavage) 100 mg kg1 d1
(maternal and
LD50 (bobwhite quail, oral) 2000 mg/kg developmental)
LC50 (rainbow trout, 96-h) 77.6 mg/L Rat (2-generation feed) 1416 mg kg1 d1
EC50 (daphnia magna, 48-h) 107 mg/L (parental and
EC50 (algae, 72-h) 1.57 mg/L developmental)
LD50 (honeybee, contact) 200 mg/bee Dog (1-year feed) 24.929.6 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil Mouse (18-month feed) 93.9116.9 mg kg1 d1
Rat (2-year feed) 36.440.0 mg kg1 d1
RfD 0.14 mg kg1 d1
ARfD 2.5 mg kg1 d1

Pyroxsulam [422556-08-9]
Mammalian [2, 271, 272, 471]:
Ecological [2, 3, 530]:
LD50 (rat, oral) >2000 mg/kg
LD50 (rat, dermal) >2000 mg/kg
LD50 (mallard duck, oral) 2250 mg/kg
LC50 (rat, 4-h inhalation) >5.1 mg/L air
LC50 (bluegill sunfish, 96-h) 94 mg/L
Rabbit: slightly irritating
EC50 (daphnia magna, 48-h) 60.4 mg/L
to skin and eyes
EC50 (algae, 72-h) 32.8 mg/L
Guinea pig: a skin sensitizer
LD50 (honeybee, contact) 25.1 mg/bee
Nonmutagenic
NOEL/NOAEL:
Rat (teratogenicity, gavage) 1000 mg kg1 d1
(maternal and
developmental) Thiencarbazone [317815-83-1]
Rabbit (teratogenicity, gavage) 600 mg kg1 d1 Mammalian [2, 531]:
(maternal)
Rabbit (teratogenicity, gavage) 300 mg kg1 d1
(developmental) LD50 (rat, oral) >2000 mg/kg
Rat (2-generation feed) 1000 mg kg1 d1 LD50 (rat, dermal) >2000 mg/kg
(parental and LC50 (rat, 4-h inhalation) 2.018 mg/L air
developmental) Nonmutagenic
Vol. 39 Weed Control, 2. Individual Herbicides 337
NOEL/NOAEL: EC50 (daphnia magna, 48-h) 119 mg/L
Rat (2-year feed) 234 mg kg1 d1 EC50 (algae, 72-h) 0.013 mg/L
Dog (1-year feed) 117 mg kg1 d1 LD50 (honeybee) 100 mg/bee
Mouse (78-week feed) 147 mg kg1 d1
Rat (2-generation feed) 245 mg kg1 d1
(parental and
developmental)
Rabbit (teratogenicity, gavage) 125 mg kg1 d1
Butafenacil [134605-64-4]
(maternal and Mammalian [2, 279, 533]:
developmental)
RfD 1.17 mg kg1 d1
LD50 (rat, oral) >5000 mg/kg
LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 5.1 mg/L air
Rabbit: skin and eye irritant
Ecological [2, 275]: Guinea pig: a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
LD50 (bird, oral) 2000 mg/kg
Rat (2-year feed) 1.14-1.30 mg kg1 d1
LC50 (rainbow trout, 96-h) 104 mg/L
Mouse (78-week feed) 1.2 mg kg1 d1
EC50 (daphnia magna, 48-h) 98.6 mg/L
Dog (1-year feed) 100 mg kg1 d1
EC50 (algae, 72-h) 1.02 mg/L
Rat (2-generation feed) 1.53.3 mg kg1 d1
LD50 (honeybee, oral) 199 mg/bee
(parental)
Rat (2-generation feed) >50 mg kg1 d1
(developmental)
Rabbit (teratogenicity, gavage) 100 mg kg1 d1
2.10. Uracils (maternal and
developmental)
Benzfendizone [158755-95-4] No data are RfD 0.012 mg kg1 d1

yet available in the public domain.

Bromacil [314-40-9] Ecological [2, 279]:

Mammalian [13, 5, 277, 462, 532]:
LD50 (mallard duck, oral) 2250 mg/kg
LD50 (rat, oral) 13005175 mg/kg
LC50 (rainbow trout, 96-h) 3.9 mg/L
LD50 (mouse, oral) 3040 mg/kg
EC50 (daphnia magna, 48-h) 8.6 mg/L
LD50 (rabbit, dermal) > 5000 mg/kg
EC50 (algae, 72-h) 0.0025 mg/kg
LC50 (rat, 4-h inhalation) > 4.8 mg/L air
LD50 (honeybee, oral) >20 mg/bee
Rabbit: moderately irritating to skin
LC50 (earthworm, 14-d) 1250 mg/kg soil
Rabbit: mildly irritating to eyes
Guinea pig: not a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
Rat (3-generation feed) ca. 12.5 mg kg1 d1 Lenacil [2164-08-1]
Rat (teratogenicity, gavage) 20 mg kg1 d1 Mammalian [1, 2, 280, 281, 471]:
(maternal)
75 mg kg1 d1
(developmental) LD50 (rat, oral) > 5000 mg/kg
Rabbit (teratogenicity, gavage) 100 mg kg1 d1 LD50 (rabbit, dermal) > 5000 mg/kg
(maternal and LC50 (rat, 4-h inhalation) > 5.12 mg/L air
developmental) Rabbit: nonirritating to skin and eyes
Rat (2-year feed) ca. 2.5 mg kg1 d1 Guinea pig: not a skin sensitizer
Dog (1-year feed) ca. 17 mg kg1 d1 Nonmutagenic
Mouse (18-month feed) 12.5 mg kg1 d1 NOEL/NOAEL: mg kg1 d1
ADI 0.13 mg kg1 d1 Rat (2-year feed) 12 mg kg1 d1
Mouse (18-month feed) 332 mg kg1 d1
Rat (2-generation feed) 81.9 mg kg1 d1
Rat (2-generation feed) 1727 mg kg1 d1
Ecological [13, 5, 277]: Rabbit (teratogenicity, gavage) 1000 mg kg1 d1
Rabbit (teratogenicity, gavage) 4000 mg kg1 d1
ADI 0.120.13 mg kg1 d1
LD50 (bobwhite quail, oral 2250 mg/kg AOEL 0.40 mg kg1 d1
LC50 (bluegill sunfish, 96-h) 36 mg/L
338 Weed Control, 2. Individual Herbicides Vol. 39
Guinea pig: not a sensitizer
Ecological [2, 281, 480]: Nonmutagenic
NOEL/NOAEL:
LD50 (mallard duck, oral) >2000 mg/kg Rabbit (teratogenicity, gavage) 104 mg kg1 d1
LC50 (rainbow trout, 96-h) 2 mg/L (maternal)
EC50 (daphnia magna, 48-h) 8.4 mg/L Rabbit (teratogenicity, gavage) 260 mg kg1 d1
EC50 (algae, 72-h) 0.0077 mg/L (developmental)
LD50 (honeybee, contact) 25 mg/bee Rat (teratogenicity, gavage) 520 mg kg1 d1
LC50 (earthworm, 14-d) >10 000 mg/kg soil (maternal and
developmental)
Rat (2-generation feed) 1000 mg kg1 d1
(parental and
developmental)
Saflufenacil [372137-35-4] No data are yet Dog (1-year feed) 9399 mg kg1 d1
in the public domain available. Rat (2-year feed) 50 mg kg1 d1
Mouse (78-week feed) 2501000 mg kg1 d1
RfD 0.5 mg kg1 d1
Terbacil [5902-51-2]
ADI/ARfD/AOEL 0.26 mg kg1 d1
Mammalian [2, 5, 283, 462, 495, 534]

LD50 (rat, oral) 9341255 mg/kg

LD50 (rabbit, dermal) > 5000 mg/kg Ecological [2, 284, 285]:
LC50 (rat, 4-h inhalation) > 4.4 mg/L air
Rabbit: nonirritating to skin
Rabbit: slightly irritating to eyes LD50 (bobwhite quail, oral) >2250 mg/kg
Guinea pig: not a skin sensitizer LC50 (rainbow trout, 96-h) >100 mg/L
Nonmutagenic EC50 (daphnia magna, 48-h) >98.6 mg/L
NOEL/NOAEL: EC50 (algae, 72-h) 30 mg/L
Rat (3-generation feed) 30 mg kg1 d1 LD50 (honeybee, oral) >117 mg/bee
Rat (teratogenicity, gavage) 62.5 mg kg1 d1 LC50 (earthworm, 14-d) 100 mg/kg soil
(maternal)
Rabbit (teratogenicity, gavage) 200 mg kg1 d1
(maternal and
developmental)
Rat (2-year feed) ca. 12.5 mg kg1 d1 Clopyralid [1702-17-6]
Dog (2-year feed) ca. 1.25 mg kg1 d1 Mammalian [13, 287, 462, 495, 536]:
Mouse (2-year feed) 7 mg kg1 d1
ADI 0.0125 mg kg1 d1
LD50 (rat, oral) 26754300 mg/kg
LD50 (mouse, oral) > 5000 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg
Ecological [2, 5, 283]: LC50 (rat, 4-h inhalation) 1.3 mg/L air
Rabbit: slightly irritating to skin
Rabbit: severely irritating to eyes
LD50 (pheasant, oral) 2250 mg/kg Guinea pig: a skin sensitizer
LC50 (rainbow trout, 96-h) 46 mg/L Nonmutagenic
EC50 (daphnia magna, 48-h) 65 mg/L NOEL/NOAEL:
EC50 (algae, 72-h) 0.042 mg/L Rat (2-generation feed) 500 mg kg1 d1
LD50 (honeybee) 50 mg/bee (parental)
Rat (2-generation feed) >1500 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) >75 mg kg1 d1
2.11. Pyridines (maternal)
Rat (teratogenicity, gavage) >250 mg kg1 d1
(developmental)
Aminopyralid [150114-71-9] Rabbit (teratogenicity, gavage) 110 mg kg1 d1
Mammalian [2, 284, 285, 535]: (maternal and
developmental)
Rat (2-year feed) 50 mg kg1 d1
LD50 (rat, oral) >5000 mg/kg Dog (1-year feed) 100 mg kg1 d1
LD50 (rat, dermal) >5000 mg/kg Mouse (18-month feed) 500 mg kg1 d1
LC50 (rat, 4-h inhalation) 5.79 mg/L air ADI/AOEL 0.15 mg kg1 d1
Rabbit: nonirritating to skin RfD 0.5 mg kg1 d1
Rabbit: slightly irritant to eyes
Vol. 39 Weed Control, 2. Individual Herbicides 339
1 1
Rabbit (teratogenicity, gavage) 100 mg kg d
Ecological [13]: (maternal and
developmental)
Rat (2-generation feed) 2742 mg kg1 d1
LD50 (mallard duck, oral) 1465 mg/kg (parental)
LC50 (rainbow trout, 96-h) 99.9103 mg/L Rat (2-generation feed) 113176 mg kg1 d1
EC50 (daphnia magna, 48.h) 99 mg/L (developmental)
EC50 (algae, 72-h) 30.5 mg/L Dog (1-year feed) 2628 mg kg1 d1
LD50 (honeybee, contact) 98 mg/bee Mouse (78-week feed) 10041037 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil Rat (2-year feed) 236323 mg kg1 d1
ADI/RfD 0.26 mg kg1 d1
ARfD 1.0 mg kg1 d1

Diflufenican [83164-33-4]
Mammalian [2, 289, 290, 471]:
Ecological [13]:

LD50 (rat, oral) > 2000 mg/kg

LD50 (bobwhite quail, oral) 2250 mg/kg
LD50 (mouse, oral) > 1000 mg/kg
LC50 (rainbow trout, 96-h) 106 mg/L
LD50 (rabbit, oral) > 5000 mg/kg
EC50 (daphnia magna, 48-h) 15 mg/L
LD50 (rat, dermal) > 2000 mg/kg
EC50 (algae, 72-h) 0.11 mg/L
LC50 (rat, 4-h inhalation) 5.12 mg/L air
LD50 (honeybee, contact) 90 mg/bee
Rabbit: nonirritating to skin
Rabbit: eye irritant
Guinea pig: not a skin sensitizer
Nonmutagenic
NOEL/NOAEL: Dithiopyr [97886-45-8]
Dog (1-year feed) 100 mg kg1 d1 Mammalian [1, 2, 293, 462, 471, 538, 539]:
Rat (2-year feed) 25 mg kg1 d1
Mouse (104-week feed) 6073 mg kg1 d1
Rat (2-generation feed) 25 mg kg1 d1 LD50 (rat, oral) > 5000 mg/kg
ADI 0.2 mg kg1 d1 LD50 (mouse, oral) > 5000 mg/kg
AOEL 0.11 mg kg1 d1 LD50 (rat, dermal) > 5000 mg/kg
LD50 (rabbit, dermal) > 5000 mg/kg
LC50 (rat, 4-h inhalation) >6 mg/L air
Rabbit: irritating to skin
Rabbit: slightly irritating to eyes
Ecological [2, 289]: Guinea pig: a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
LD50 (mallard duck, oral) 2150 mg/kg Rat (2-generation feed) 1.7 mg kg1 d1
LC50 (rainbow trout, 96-h) 0.099 mg/L (parental)
EC50 (daphnia magna, 48-h) 0.24 mg/L ca. 150 mg kg1 d1
EC50 (algae, 72-h) 0.00025 mg/L (developmental)
LD50 (honeybee, contact) 100 mg/bee Rat (teratogenicity, gavage) 300 mg kg1 d1
LC50 (earthworm, 14-d) 500 mg/kg soil (maternal)
Rat (teratogenicity, gavage) 1000 mg kg1 d1
(developmental)
Rabbit (teratogenicity, gavage) 500 mg kg1 d1
Diflufenzopyr [109293-97-2] (maternal)
Rabbit (teratogenicity, gavage) 1000 mg kg1 d1
Mammalian [13, 537]: (developmental)
Rat (2-year feed) 0.36 mg kg1 d1
LD50 (rat, oral) > 5000 mg/kg Dog (1-year feed) ca. 0.5 mg kg1 d1
LD50 (rabbit, dermal) > 5000 mg/kg Mouse (18-month feed) ca. 0.31 mg kg1 d1
LC50 (rat, 4-h inhalation) 2.93 mg/L air ADI 0.0050.05 mg kg1 d1
Rabbit: eye irritant
Rabbit: not a skin irritant
Guinea pig: not sensitizing
Nonmutagenic Ecological [1, 2, 480, 540]:
NOEL/NOAEL:
1 1
Rat (teratogenicity, gavage) 300 mg kg d
(maternal and LD50 (mallard duck, oral) 5620 mg/kg
developmental) LC50 (rainbow trout, 96-h) 0.36 mg/L
340 Weed Control, 2. Individual Herbicides Vol. 39
EC50 (daphnia magna, 48-h) 14 mg/L Nonmutagenic
EC50 (algae, 2-h) 0.02 mg/L NOEL/NOAEL:
LD50 (honeybee, contact) 53 mg/bee Rat (2-generation feed) 200 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil (parental)
Rat (2-generation feed) 1000 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) > 400 mg kg1 d1
Rabbit (teratogenicity, gavage) 34 mg kg1 d1
Fluroxypyr-meptyl [81406-37-3] (maternal)
Mammalian [13, 295, 296]: Rabbit (teratogenicity, gavage) 344 mg kg1 d1
(developmental)
Rat (2-year feed) 20 mg kg1 d1
LD50 (rat, oral) >2000 mg/kg
Dog (1-year feed) 35 mg kg1 d1
LD50 (rabbit, dermal) >2000 mg/kg
Mouse (2-year feed) 500 mg kg1 d1
LC50 (rat, 4-h inhalation) 1.0 mg/L air
ADI/ARfD/AOEL 0.3 mg kg1 d1
Rabbit: nonirritating to skin
RfD 0.2 mg kg1 d1
Rabbit: mildly irritating to eyes
Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) 100500 mg kg1 d1 Ecological [13, 298]:
(parental)
Rat (2-generation feed) 300 mg kg1 d1
(developmental) LD50 (mallard duck, oral) 1944 mg/kg
Rat (teratogenicity, gavage) 125 mg kg1 d1 LC50 (rainbow trout, 96-h) 8.8 mg/L
(maternal) EC50 (daphnia magna, 48-h) 44 mg/L
Rat (teratogenicity, gavage) 250 mg kg1 d1 EC50 (algae, 72-h) 60 mg/L
(developmental) LD50 (honeybee, oral) 74 mg/bee
Rabbit (teratogenicity, gavage) 250 mg kg1 d1 LC50 (earthworm, 14-d) 4475 mg/kg soil
(maternal)
Rabbit (teratogenicity, gavage) 100 mg kg1 d1
(developmental)
Rat (2-year feed) 100 mg kg1 d1 Picolinafen [137641-05-5]
Mouse (18-month feed) 300 mg kg1 d1 Mammalian [2, 300, 301, 541]:
Dog (1-year feed) 150 mg kg1 d1
ADI/AOEL 0.8 mg kg1 d1
LD50 (rat, oral) >5000 mg/kg
RfD 0.50.8 mg kg1 d1
LD50 (rat, dermal) >5000 mg/kg
ARfD 0.33 mg kg1 d1
LC50 (rat, 4-h inhalation) >5.9 mg/L air
Rabbit: slight eye irritant
Rabbit: not a skin irritant
Guinea pig: not a sensitizer
Ecological [13, 295, 296]: Nonmutagenic
NOEL/NOAEL:
Mouse (78-week feed) 6.98.2 mg kg1 d1
LD50 (mallard duck, oral) >2000 mg/kg Rat (2-year feed) 2.43.0 mg kg1 d1
LC50 (rainbow trout, 96-h) 0.2 mg/L Dog (1-year feed) >1.4 mg kg1 d1
EC50 (daphnia magna, 48-h) 0.2 mg/L Rat (2-generation feed) 3.74.2 mg kg1 d1
EC50 (algae, 72-h) 0.5 mg/L (parental)
LD50 (honeybee, oral) 100 mg/bee Rat (teratogenicity, gavage) 50 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil (maternal)
Rat (teratogenicity, gavage) 500 mg kg1 d1
(developmental)
Rabbit (teratogenicity, gavage) 5 mg kg1 d1
Picloram [1918-02-1] (maternal)
Rabbit (teratogenicity, gavage) 20 mg kg1 d1
Mammalian [13, 298, 299, 462]: (developmental)
ADI 0.0070.014 mg kg1 d1
LD50 (rat, oral) 4012 to > 5000 mg/kg ARfD 0.05 mg kg1 d1
LD50 (mouse, oral) 20004000 mg/kg AOEL 0.03 mg kg1 d1
LD50 (rabbit, oral) ca. 2000 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 0.035 mg/L air
Rabbit: mildly irritating to skin
Ecological [2, 300, 301]:
Rabbit: moderately
irritating to eyes LD50 (mallard duck, oral) 2250 mg/kg
Guinea pig: not a skin sensitizer LC50 (rainbow trout, 96-h) 0.281 mg/L
Vol. 39 Weed Control, 2. Individual Herbicides 341
EC50 (daphnia magna, 48-h) 0.45 mg/L Rabbit (teratogenicity, gavage) 30 mg kg d1
1

EC50 (algae, 72-h) 0.025 mg/L (maternal and

LD50 (honeybee, oral) 200 mg/bee developmental)
LC50 (earthworm, 14-d) 1000 mg/kg soil Rat (2-generation feed) 5 mg kg1 d1
(parental and
developmental)
Dog (1-year feed) 5 mg kg1 d1
Rat (2-year feed) 12 mg kg1 d1
Thiazopyr [117718-60-2] Mouse (78-week feed) 84 mg kg1 d1
Mammalian [13, 303, 462, 495, 542, 543]: ADI 0.03 mg kg1 d1
ARfD 0.3 mg kg1 d1
RfD/AOEL 0.05 mg kg1 d1
LD50 (rat, oral) > 5000 mg/kg
ARfD 1.0 mg kg1 d1
LD50 (rabbit, dermal) > 5000 mg/kg
LC50 (rat, 4-h inhalation) > 1.2 mg/L air
Rabbit: nonirritating to skin
Rabbit: slightly irritating to eyes
Guinea pig: not Ecological [13]:
a skin sensitizer
Nonmutagenic
NOEL/NOAEL: LD50 (mallard duck, oral) 1698 mg/kg
Rat (2-year feed) 4.4 mg kg1 d1 LC50 (rainbow trout, 96-h) 117 mg/L
(parental) EC50 (daphnia magna, 48-h) 131 mg/L
Dog (1-year feed) 0.8 mg kg1 d1 EC50 (algae, 72-h) 76 mg/L
Mouse (78-week feed) 1.6 mg kg1 d1 LD50 (honeybee, contact) >100 mg/bee
Rat (2-generation feed) 0.72 mg kg1 d1 LC50 (earthworm, 14-d) 1440 mg/kg/soil
(parental)
Rat (2-generation feed) 72.9 mg kg1 d1
(developmental)
Rabbit (teratogenicity, gavage) 75 mg kg1 d1
(maternal)
2.12. (Thio)carbamates
Rabbit (teratogenicity, gavage) 175 mg kg1 d1
(developmental) Asulam [3337-71-1]
RfD 0.008 mg kg1 d1 Mammalian [2, 307, 462, 466]:

LD50 (rat, oral) > 5000 mg/kg

Ecological [13, 303, 542]: LD50 (mouse, oral) > 4000 mg/kg
LD50 (rabbit, oral) > 4000 mg/kg
LD50 (dog, oral) > 4000 mg/kg
LD50 (bobwhite quail, oral) 1913 mg/kg LD50 (rat, dermal) > 2000 mg/kg
LC50 (rainbow trout, 96-h) 3.2 mg/L LD50 (rabbit, dermal) > 2000 mg/kg
EC50 (daphnia magna, 48-h) 6.1 mg/L LC50 (rat, 6-h inhalation) > 1.8 mg/L air
EC50 (algae, 72-h) 0.04 mg/L Rabbit: slightly
LD50 (honeybee) 100 mg/bee irritating to skin
LC50 (earthworm, 14-d) 1000 mg/kg soil Rabbit: irritating to eyes
Guinea pig:
a skin sensitizer
Nonmutagenic
Triclopyr [55335-06-3] NOEL/NOAEL:
Rat (2-generation feed) 250 mg kg1 d1
Mammalian [13, 305, 462]:
(parental)
>1250 mg kg1 d1
LD50 (rat, oral) 577729 mg/kg (developmental)
LD50 (rabbit, oral) 550 mg/kg Rat (teratogenicity, gavage) 1000 mg kg1 d1
LD50 (rabbit, dermal) > 2000 mg/kg (maternal and
LC50 (rat, 4-h inhalation) 4.8 mg/L air developmental
Rabbit: irritating to skin Rabbit (teratogenicity, gavage) 750 mg kg1 d1
Rabbit: mildly irritating to eyes (maternal,
Guinea pig: a potential skin sensitizer developmental)
Nonmutagenic Rat (2-year feed) 36 mg kg1 d1
NOEL/NOAEL: Dog (6-month feed) 60 mg kg1 d1
Rat (teratogenicity, gavage) 100 mg kg1 d1 Mouse (2-year feed) 750 mg kg1 d1
(maternal and RfD 0.36 mg kg1 d1
developmental)
342 Weed Control, 2. Individual Herbicides Vol. 39

Ecological [2, 307]: Ecological [13]:

LD50 (bobwhite quail) 2000 mg/kg LD50 (mallard duck, oral) 4640 mg/kg
LC50 (rainbow trout, 96-h) 175 mg/L LC50 (rainbow trout, 96-h) 4.2 mg/L
EC50 (daphnia magna, 48-h) 2.0 mg/L EC50 (daphnia magna, 48-h) 159 mg/L
LD50 (honeybee) 36 mg/bee EC50 (algae, 72-h) 0.5 mg/L
LD50 (honeybee) 73 mg/bee

Barban [101-27-9]
Mammalian [2, 3, 466]: Carbetamide [16118-49-3]
Mammalian [1, 2]:
LD50 (rat, oral) 5271429 mg/kg
LD50 (rat, dermal) 1600 mg/kg
LC50 (rat, 4-h inhalation) 27.4 mg/L air LD50 (rat, oral) 1718>2000 mg/kg
Rabbit: skin irritant LD50 (mouse, oral) 1720 mg/kg
Rabbit: nonirritating to eyes LD50 (dog, oral) 900 mg/kg
Guinea pig: a skin sensitizer LD50 (rat, dermal) > 2000 mg/kg
Nonmutagenic LC50 (rat, 4-h inhalation) > 0.13 mg/L air
NOEL/NOAEL: Rabbit: nonirritating to skin
Rat (2-year feed) 7.5 mg kg1 d1 Rabbit: eye irritant
Dog (2-year feed) 0.125 mg kg1 d1 NOEL/NOAEL:
Rat (teratogenicity, gavage) 87 mg kg1 d1 Rat (90-d feed) ca. 203 mg kg1 d1
(maternal and Dog (90-d feed) ca. 350 mg kg1 d1
developmental) ADI 0.021 mg kg1 d1
ARfD 0.05 mg kg1 d1
AOEL 0.03 mg kg1 d1

Ecological [2, 3]:

Ecological [1, 2]:
LC50 (rainbow trout, 96-h) 0.6 mg/L
EC50 (daphnia magna, 48-h) 0.3 mg/L
EC50 (algae, 72-h) 10 mg/L
LD50 (bobwhite quail, oral) 2000 mg/kg
LC50 (rainbow trout, 96-h) 100 mg/L
EC50 (daphnia magna, 48-h) 81 mg/L
EC50 (algae, 72-h) 520 mg/L
Butylate [2008-41-5] LD50 (honeybee, contact) 500 mg/bee
Mammalian [13, 462, 466, 495, 544]: LC50 (earthworm, 14-d) 660 mg/kg soil

LD50 (rat, oral) 35005430 mg/kg

LD50 (guinea pig, oral) 1660 mg/kg
LD50 (rabbit, dermal) > 5000 mg/kg
Chlorbufam [1967-16-4]
LC50 (rat, 4-h inhalation) 5.2 mg/L air Mammalian [13, 461]:
Rabbit: mildly irritating to skin
Rabbit: nonirritating to eyes
Guinea pig: not a skin sensitizer LD50 (rat, oral) 2380 mg/kg
Nonmutagenic LD50 (mouse, i.p.) 250 mg/kg
NOEL/NOAEL: Rabbit: skin and eye irritant
Rat (2-year feed) 50 mg kg1 d1 NOEL/NOAEL:
Dog (1-year feed) 5 mg kg1 d1 Rat (4-month feed) 20 mg kg1 d1
Mouse (2-year feed) 20 mg kg1 d1 ADI 0.05 mg kg1 d1
Rat (2-generation feed) 10 mg kg1 d1
(parental and
developmental)
Rabbit (teratogenicity, gavage) 100 mg/kg/s Ecological [13]:
(maternal)
Rabbit (teratogenicity, gavage) 500 mg kg1 d1
(developmental) LC50 (mud snail, 48-h) 18 mg/L
RfD 0.05 mg kg1 d1 LC50 (European physa, 48-h) 10 mg/L
Vol. 39 Weed Control, 2. Individual Herbicides 343
1 1
Rabbit (teratogenicity, gavage) 300 mg kg d
Chlorpropham [101-21-3] (developmental)
Mammalian [13, 312, 313]: Rat (2-generation feed) 2.5 mg kg1 d1
parental and
developmental)
LD50 (rat, oral) 412007500 mg/kg RfD 0.05 mg kg1 d1
LD50 (rat, dermal) >2000 mg/kg ARfD 0.066 mg kg1 d1
LD50 (rabbit, oral) >2000 mg/kg
LC50 (rat, 4-h inhalation) 0.5 mg/L air
Rabbit: skin and eye irritant
Guinea pig: not a sensitizer Ecological [13, 315]:
Nonmutagenic
NOEL/NOAEL:
Rat (2-year feed) 30 mg kg1 d1 LD50 (Japanese quail, oral) 2000 mg/kg
Dog (60-week feed) 5 mg kg1 d1 LC50 (rainbow trout, 96-h) 4.5 mg/L
Mouse (78-week feed) 100 mg kg1 d1 EC50 (daphnia magna, 48-h) 24 mg/L
Rat (teratogenicity, gavage) 100 mg kg1 d1 LD50 (honeybee, contact) 29 mg/bee
(maternal) LC50 (earthworm, 14-d) 250 mg/kg soil
Rat (teratogenicity, gavage) 350 mg kg1 d1
(developmental)
Rabbit (teratogenicity, gavage) 250 mg kg1 d1
(maternal and Desmedipham [13684-56-5]
developmental) Mammalian [1, 2, 317, 318, 462, 495]:
Rat (2-generation feed) 50 mg kg1 d1
(parental)
Rat (2-generation feed) 500 mg kg1 d1 LD50 (rat, oral) > 10 250 mg/kg
(developmental) LD50 (mouse, oral) > 5000 mg/kg
ADI/AOEL 0.05 mg kg1 d1 LD50 (rabbit, dermal) > 4000 mg/kg
ARfD 0.5 mg kg1 d1 LC50 (rat, 4-h inhalation) > 7.4 mg/L air
Rabbit: skin and eye irritant
Guinea pig: not a skin sensitizer
NOEL/NOAEL:
Rat (2-year feed)  3.2 mg kg1 d1
Ecological [13, 312, 313]: Mouse (2-year feed) 2225 mg kg1 d1
ADI: 0.03 mg kg1 d1
ARfD 0.1 mg kg1 d1
LD50 (mallard duck, oral) >2000 mg/kg
AOEL 0.04 mg kg1 d1
LC50 (rainbow trout, 96-h) 5.7 mg/L
EC50 (daphnia magna, 48-h) 2.6 mg/L
EC50 (algae, 72-h) 1 mg/L
LD50 (honeybee, contact) 86 mg/bee
Ecological [1, 2, 317, 318]:

LD50 (bobwhite quail, oral) 2000 mg/kg

Cycloate [1134-23-2] LC50 (bluegill sunfish, 96-h) 0.25 mg/L
Mammalian [13, 315, 462, 495]: EC50 (daphnia magna, 48-h) 0.45 mg/L
EC50 (algae, 72-h) 0.01 mg/L
LD50 (honeybee, contact) 25 mg/bee
LD50 (rat, oral) 22753200 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) 4.7 mg/L air
Rabbit: mildly irritating Dimepiperate [61432-55-1]
to skin and eyes Mammalian [1, 2]:
Guinea pig: a potential
skin sensitizer
NOEL/NOAEL: LD50 (rat, oral) 946959 mg/kg
Rat (2-year feed) 0.5 mg kg1 d1 LD50 (mouse, oral) 45194677 mg/kg
Dog (13-year feed) 0.5 mg kg1 d1 LD50 (rat, dermal) > 5000 mg/kg
Mouse (78-week feed) 49 mg kg1 d1 LC50 (rat, 4-h inhalation) > 1.66 mg/L air
Rat (teratogenicity, gavage) 75 mg kg1 d1 Rabbit: irritating to skin and eyes
(maternal) Guinea pig: a skin sensitizer
Rat (teratogenicity, gavage) 400 mg kg1 d1 NOEL/NOAEL:
(developmental) Rat (2-year feed) 0.1 mg kg1 d1
Rabbit (teratogenicity, gavage) 30 mg kg1 d1 ADI 0.001 mg kg1 d1
(maternal)
344 Weed Control, 2. Individual Herbicides Vol. 39

Ecological [1, 2]: Ecological [1, 2]:

LD50 (Japanese quail, oral) 2000 mg/kg LD50 (Japanese quail, oral) 2000 mg/kg
LC50 (rainbow trout, 96-h) 5.7 mg/L LC50 (carp, 96-h) 1.52 mg/L
EC50 (daphnia magna, 48-h) 40 mg/L

Karbutilate [4849-32-5]
EPTC [759-94-4] Mammalian [2, 545]:
Mammalian [13, 462, 466]:
LD50 (rat, oral) 3000>5000 mg/kg
LD50 (rat, dermal) 154 000 mg/kg
LD50 (rat, oral) 9161652 mg/kg LD50 (mouse, oral) 1000>5000 mg/kg
LD50 (mouse, oral) 3160 mg/kg LC50 (rat, 4-h inhalation) 3.7 mg/L air
LD50 (rabbit, oral) 2640 mg/kg Rabbit: nonirritating to skin
LD50 (rat, dermal) 3200 mg/kg Rabbit: eye irritant
LD50 (rabbit, dermal) 5000 mg/kg Guinea pig: not a sensitizer
LC50 (rat, 4-h inhalation) 3.84.3 mg/L air NOEL/NOAEL:
Rabbit: mild-moderately ADI 0.005 mg kg1 d1
irritating to skin and eyes
Guinea pig: a weak skin sensitizer
Nonmutagenic
NOEL/NOAEL: Ecological [2, 480]:
Rat (gavage) 100 mg kg1 d1
(maternal and
LD50 (mallard duck, oral) 4640 mg/kg
developmental)
LC50 (rainbow trout, 96-h) 75>135 mg/L
Rat (2-year feed) 5 mg kg1 d1
EC50 (daphnia magna, 48-h) 463 mg/L
Dog (1-year feed) 15 mg kg1 d1
EC50 (algae, 4-h) 25 mg/L
Mouse (2-year feed) 20 mg kg1 d1
Rat (2-generation feed) 2.5 mg kg1 d1
RfD 0.025 mg kg1 d1
Molinate [2212-67-1]
Mammalian [13, 321, 332, 462]:
Ecological [13]:
LD50 (rat, oral) 483-720 mg/kg
LD50 (mouse, oral) 795 mg/kg
LD50 (mallard duck, oral) 1000 mg/kg LD50 (rat, dermal) 40004800 mg/kg
LC50 (bluegill sunfish, 96-h) 14 mg/L LD50 (rabbit, dermal) > 4640 mg/kg
EC50 (daphnia magna, 48-h) 14 mg/L LC50 (rat, 4-h inhalation) 1.36 mg/L air
EC50 (algae, 72-h) 5.46 mg/L Rabbit: mildly irritating to skin
LD50 (honeybee, oral) 0.011 mg/bee Rabbit: severely irritating to eyes
LC50 (earthworm, 14-d) 267 mg/kg soil Guinea pig: a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) < 3.2 mg kg1 d1
Esprocarb [85787-20-2] (parental and
developmental)
Mammalian [1, 2]: Rat (2-year feed) 1 mg kg1 d1
Dog (90-day feed) 20 mg kg1 d1
LD50 (rat, oral) >2000-3700 mg/kg ADI/AOEL 0.008 mg kg1 d1
LD50 (rat, dermal) > 2000 mg/kg ARfD 0.1 mg kg1 d1
LC50 (rat, 4-h inhalation) > 4.0 mg/L air
Rabbit: mildly irritating
to skin and eyes
Guinea pig: not a skin sensitizer Ecological [13, 321]:
Nonmutagenic
NOEL/NOAEL:
Rat (2-year feed) 1.1 mg kg1 d1 LD50 (mallard duck, oral) 389 mg/kg
Dog (1-year feed) 1.0 mg kg1 d1 LC50 (rainbow trout, 96-h) 16 mg/L
ADI 0.01 mg kg1 d1 EC50 (daphnia magna, 48-h) 15 mg/L
EC50 (algae, 72-h) 0.5 mg/L
Vol. 39 Weed Control, 2. Individual Herbicides 345
LD50 (honeybee, oral) 11 mg/bee EC50 (daphnia magna, 48-h) 5.9 mg/L
LC50 (earthworm, 14-d) 289 mg/kg soil EC50 (algae, 72-h) 8.2 mg/L
LD50 (honeybee,) 11 mg/bee

Orbencarb [34622-58-7] Phenmedipham-methyl [13684-63-4]

Mammalian [1, 2, 546]: Mammalian [13, 326, 327, 462, 495]:
LD50 (rat, oral) 800820 mg/kg LD50 (rat, oral) > 8000 mg/kg
LD50 (mouse, oral) 9351010 mg/kg LD50 (mouse, oral) > 8000 mg/kg
LD50 (rat, dermal) > 3000 mg/kg LD50 (dog, oral) > 4000 mg/kg
LC50 (rat, 4-h inhalation) 2.944.32 mg/L air LD50 (rabbit, dermal) 1000 mg/kg
Rabbit: nonirritating LC50 (rat, 4-h inhalation) 6.2 mg/L air
to skin and eyes Rabbit: a skin irritant
NOEL/NOAEL: Rabbit: nonirritating to eyes
Rat (90-day feed) 0.690.75 mg kg1 d1 Guinea pig: not a skin sensitizer
ADI 0.01 mg kg1 d1 NOEL/NOAEL:
Rat (2-year feed) 25 mg kg1 d1
Dog (2-year feed) >25 mg kg1 d1
Rat (3-generation feed) >25 mg kg1 d1
Ecological [1, 2]: (parental and
developmental)
LD50 (mallard duck, oral) 2000 mg/kg Rat (teratogenicity, gavage) >25 mg kg1 d1
LC50 (carp, 96-h) 3.4 mg/L (maternal and
EC50 (daphnia magna, 48-h) 2.88 mg/L developmental)
LD50 (honeybee, oral) 103 mg/bee ADI 0.03 mg kg1 d1
AOEL 0.13 mg kg1 d1
RfD 0.25 mg kg1 d1

Pebulate [1114-71-2]
Mammalian [13, 324, 462, 495]: Ecological [13, 327]:

LD50 (rat, oral) 1675-11209 mg/kg LD50 (mallard duck, oral) 2100 mg/kg
LD50 (mouse, oral) 15291784 mg/kg LC50 (rainbow trout, 96-h) 0.021.71 mg/L
LD50 (rabbit, dermal) 4640 mg/kg EC50 (daphnia magna, 48-h) 0.41 mg/L
LC50 (rat, 4-h inhalation) > 3.5 mg/L air EC50 (algae, 72-h) 0.086 mg/L
Rabbit: mildly irritating LD50 (honeybee, contact) 50 mg/bee
to skin and eyes LC50 (earthworm, 14-d) 244 mg/kg soil
Guinea pig: not a skin
sensitizer
Nonmutagenic Propham [122-42-9]
NOEL/NOAEL:
Rat (2-year feed) 0.740.85 1
mg kg d 1 Mammalian [13, 328, 466]:
Dog (1-year feed) 5 mg kg1 d1
Mouse (18-month feed) 3447 mg kg1 d1 LD50 (rat, oral) 50009000 mg/kg
Rat (2-generation feed) 0.8 mg kg1 d1 LD50 (rabbit, dermal) 102 000 mg/kg
(parental) LC50 (rat, 4-h inhalation) 24 mg/L air
Rat (2-generation feed) 6 mg kg1 d1 Rabbit: skin irritant
(developmental) Rabbit: nonirritating to eyes
Rabbit (teratogenicity, gavage) 30 mg kg1 d1 Guinea pig: not a sensitizer
(maternal) Nonmutagenic
Rabbit (teratogenicity, gavage) 150 mg kg1 d1 NOEL/NOAEL:
(developmental) Rat (18-month feed) 1000 mg kg1 d1
RfD 0.0007 mg kg1 d1 Dog (90-d feed) 50 mg kg1 d1
ARfD 0.5 mg kg1 d1 Mouse (18-month feed) 150 mg kg1 d1
RfD 0.02 mg kg1 d1

Ecological [13, 324]: Ecological [13]:

LD50 (mallard duck, oral) 5206 mg/kg LD50 (mallard duck, oral) >2000 mg/kg
LC50 (bluegill sunfish, 96-h) 7.4 mg/L LC50 (bluegill sunfish, 96-h) 32 mg/L
346 Weed Control, 2. Individual Herbicides Vol. 39
EC50 (daphnia magna, 48-h) 23 mg/L
EC50 (algae, 72-h) 26 mg/L
Thiobencarb [28249-77-6]
LD50 (honeybee, contact) 16 mg/bee Mammalian [13, 462, 495]:

LD50 (rat, oral) 9201903 mg/kg

Prosulfocarb [52888-80-9] LD50 (mouse, oral) 560-2745 mg/kg
Mammalian [1, 2, 330, 331]: LD50 (rat, dermal) > 2000 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 1-h inhalation) >3 mg/L air
LD50 (rat, oral) 18201958 mg/kg Rabbit: mildly irritating to skin
LD50 (rabbit, dermal) > 2000 mg/kg Rabbit: moderately irritating to eyes
LC50 (rat, 4-h inhalation) > 4.7 mg/L air Nonmutagenic
Rabbit: slightly irritating to skin NOEL/NOAEL:
Rabbit: mildly irritating to eyes Rat (2-generation feed) <2 mg kg1 d1
Guinea pig: not a skin sensitizer Rat (teratogenicity, gavage) 25 mg kg1 d1
Nonmutagenic Rabbit (teratogenicity, gavage) 100 mg kg1 d1
NOEL/NOAEL: Rat (2-year feed) 0.91.0 mg kg1 d1
Dog (90-day feed) 110 mg kg1 d1 Dog (1-year feed) 1.0 mg kg1 d1
Rat (2-year feed) 0.5 mg kg1 d1 Mouse (18-month feed) 25 mg kg1 d1
Mouse (18-month feed) > 65 mg kg1 d1 ADI 0.009 mg kg1 d1
ADI 0.005 mg kg1 d1
ARfD 0.1 mg kg1 d1
AOEL 0.007 mg kg1 d1
Ecological [13]:

Ecological [1, 2]: LD50 (bobwhite quail, oral) 2000 mg/kg

LC50 (carp, 96-h) 0.98 mg/L
EC50 (daphnia magna, 48-h) 1.1 mg/L
LD50 (bobwhite quail, oral) 2250 mg/kg
EC50 (algae, 72-h) 0.017 mg/L
LC50 (rainbow trout, 96-h) 0.84 mg/L
LD50 (honeybee, oral) 100 mg/bee
EC50 (daphnia magna, 48-h) 0.51 mg/L
LC50 (earthworm, 14-d) 437 mg/kg soil
EC50 (algae, 72-h) 0.049 mg/L
LD50 (honeybee, oral) 80 mg/bee
LC50 (earthworm, 14-d) 71.8 mg/kg soil

Triallate [2303-17-5]
Mammalian [13, 333335, 462, 466, 495, 548]:
Pyributicarb [88678-67-5]
Mammalian [13, 471, 547]:
LD50 (rat, oral) 1100 mg/kg
LD50 (rat, dermal) >5000 mg/kg
LD50 (rat, oral) > 5000 mg/kg LC50 (rat, 12-h inhalation) > 5.3 mg/L air
LD50 (mouse, oral) > 5000 mg/kg Rabbit: slightly to moderately
LD50 (rat, dermal) > 5000 mg/kg irritating to skin
LC50 (rat, 4-h inhalation) > 6.52 mg/L air Rabbit: slightly irritating to eyes
Rabbit: slightly irritating to skin Guinea pig: not a skin sensitizer
Rabbit: nonirritating to eyes Nonmutagenic
Guinea pig: not a skin sensitizer NOEL/NOAEL:
Nonmutagenic Rat (2-generation feed) 7.5 mg kg1 d1
NOEL/NOAEL: (developmental)
Rat (2-year feed) 0.753 mg kg1 d1 Rat (teratogenicity, gavage) 30 mg kg1 d1
ADI 0.00040.0075 mg kg1 d1 (developmental)
Rabbit (teratogenicity, gavage) 15 mg kg1 d1
(developmental)
Rat (2-year feed) 2.5 mg kg1 d1
Ecological [13]: Dog (1-year feed) 2.5 mg kg1 d1
Mouse (2-year feed) 4 mg kg1 d1
Hamster (22-month feed) 18 mg kg1 d1
LC50 (carp, 96-h) 11 mg/L ADI 0.025 mg kg1 d1
EC50 (daphnia magna, 3-h) 15 mg/L ARfD 0.6 mg kg1 d1
EC50 (algae, 72-h) 0.0977 mg/L AOEL 0.032 mg kg1 d1
Vol. 39 Weed Control, 2. Individual Herbicides 347

Ecological [13]: Ecological [1, 2]:

LD50 (mallard duck, oral) 1208 mg/kg LD50 (Japanese quail, oral) 3360 mg/kg
LC50 (rainbow trout, 96-h) 0.95 mg/L LC50 (rainbow trout, 96-h) 2.8 mg/L
EC50 (daphnia magna, 48-h) 0.091 mg/L EC50 (daphnia magna, 48-h) 56 mg/L
EC50 (algae, 72-h) 0.0022 mg/L
LD50 (honeybee, contact) 100 mg/bee
LC50 (earthworm, 14-d) 2745 mg/kg soil
Bensulide [741-58-2]
Mammalian [13, 462]:
Vernolate [1929-77-7] LD50 (rat, oral) 270360 mg/kg
Mammalian [13, 199, 462, 471, 495]: LD50 (rat, dermal) > 2000 mg/kg
LD50 (rabbit, dermal) 3950 mg/kg
LC50 (rat, 4-h inhalation) > 1.75 mg/L air
LD50 (rat, oral) 12001900 mg/kg Rabbit: mildly irritating
LD50 (rabbit, dermal) 4640 mg/kg to skin and eyes
LC50 (rat, 4-h inhalation) >5 mg/L air Guinea pig: not a skin sensitizer
Rabbit: irritating to skin and eyes NOEL/NOAEL:
Guinea pig: a skin sensitizer Rat (2-year feed) 15 mg kg1 d1
Nonmutagenic Dog (1-year feed) 0.5 mg kg1 d1
NOEL/NOAEL: Mouse (90-d feed) 30 mg kg1 d1
Rat (2-generation feed) 1 mg kg1 d1 Rat (2-generation feed) 7.5 mg kg1 d1
(maternal and (parental and
developmental) developmental)
25 mg kg1 d1 Rat (teratogenicity, gavage) 5.5 mg kg1 d1
Rabbit (teratogenicity, gavage) > 200 mg kg1 d1 RfD 0.00 mg kg1 d1
(maternal and ARfD 0.15 mg kg1 d1
developmental)
Dog (90-day feed) 38 mg kg1 d1
Rat (51-week feed) 5 mg kg1 d1
Mouse (2-year feed) 100 mg kg1 d1 Ecological [13]:
ADI 0.01 mg kg1 d1

LD50 (bobwhite quail, oral) 1386 mg/kg

LC50 (rainbow trout, 96-h) 1.1 mg/L
EC50 (daphnia magna, 48-h) 0.58 mg/L
Ecological [13]:
EC50 (algae, 72-h) 0.11 mg/L
LD50 (honeybee) 1.6 mg/bee

LD50 (bobwhite quail, oral) 14 500 mg/kg

LC50 (rainbow trout, 96-h) 4.6 mg/L
EC50 (daphnia magna, 48-h) 1.8 mg/L
EC50 (algae, 72-h) 0.54 mg/L Bilanafos [35597-43-4]
LD50 (honeybee) 11 mg/bee Mammalian [1, 2, 549]:

LD50 (rat, oral) 268404 mg/kg

LD50 (hen, oral) 5000 mg/kg
2.13. Organophosphorus Compounds LD50 (rat, dermal) > 3000 mg/kg
Rat (4-h inhalation) 2.57 mg/L air
Anilofos [64249-01-0] Rabbit: nonirritating to skin and eyes
Guinea pig: not a skin sensitizer
Mammalian [1, 2]:
Nonmutagenic

LD50 (rat, oral) 472830 mg/kg

LD50 (rat, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) 26 mg/L air Ecological [1, 2]:
Rabbit: slightly irritating
to skin and eyes
Guinea pig: a sensitizer LD50 (bobwhite quail, oral) 5000 mg/kg
NOEL/NOAEL: LC50 (carp, 96-h) 1000 mg/L
1 1
ADI 0.0010.005 mg kg d EC50 (daphnia magna, 48-h) 5000 mg/L
348 Weed Control, 2. Individual Herbicides Vol. 39
Nonmutagenic
Butamifos [36335-67-8] Not neurotoxic
Mammalian [1]: NOEL/NOAEL:
Rat (2-generation feed) 6 mg kg1 d1
LD50 (rat, oral) 8451070 mg/kg (parental and
LD50 (rat, dermal) > 5000 mg/kg developmental)
LC50 (rat, 4-h inhalation) > 1.2 mg/L air Rat (teratogenicity, gavage) 2.2 mg kg1 d1
Rabbit: nonirritating to skin and eyes (maternal and
NOEL/NOAEL: developmental)
ADI 0.016 mg kg1 d1 Rabbit (teratogenicity, gavage) 2 mg kg1 d1
(maternal)
Rabbit (teratogenicity, gavage) 6.3 mg kg1 d1
(developmental)
Ecological [1, 480]: Rat (2-year feed) 2 mg kg1 d1
Dog (1-year feed) 4.5 mg kg1 d1
Mouse (2-year feed) 11 mg kg1 d1
LC50 (rainbow trout, 96-h) 4.1 mg/L
ADI/ARfD 0.021 mg kg1 d1
EC50 (algae, 72-h) 27 mg/L
AOEL 0.0021 mg kg1 d1
LC50 (carp, 96-h) 2.25 mg/L
LC50 (toad, 48-h) 3 mg/L

Ecological [13, 553]:

Fosamine [59682-52-9]
Mammalian [13, 550, 551]:
LD50 (Japanese quail, oral) 2000 mg/kg
LC50 (rainbow trout, 96-h) 710 mg/L
LD50 (rat, oral) 500024400 mg/kg EC50 (daphnia magna, 48-h) 668 mg/L
LD50 (rabbit, dermal) 168010125 mg/kg EC50 (algae, 72-h) 46.5 mg/L
LC50 (rat, 4-h inhalation) 5.6 mg/L air LD50 (honeybee, contact) 345 mg/bee
Rabbit: nonirritating to skin and eyes LC50 (earthworm, 14-d) 1000 mg/kg oil
Guinea pig: not a sensitizer
Nonmutagenic
NOEL/NOAEL:
Rat (2-year feed) 50 mg kg1 d1
Rat (one-generation feed) 250 mg kg1 d1 Glyphosate [1071-83-6]
Rat (teratogenicity, gavage) 300 mg kg1 d1 Mammalian [13, 462, 554, 555]:
RfD 0.01 mg kg1 d1

LD50 (rat, oral) 17605600 mg/kg

LD50 (mouse, oral) 11 300 mg/kg
Ecological [13, 480, 551]: LD50 (rat, dermal) > 5010 mg/kg
LD50 (rabbit, dermal) > 5000 mg/kg
LD50 (mouse, dermal) 7030 mg/kg
LD50 (mallard duck, oral) 10 000 mg/kg LC50 (rat, 4-h inhalation) 5.0 mg/L air
LC50 (rainbow trout, 96-h) >300 mg/L Rabbit: nonirritating to skin
EC50 (daphnia magna, 48-h) 1524 mg/L Rabbit: slightly irritating to eyes
EC50 (algae, 72-h) 17 mg/L Guinea pig: not a skin sensitizer
LD50 (honeybee, contact) 200 mg/bee Nonmutagenic
Non-neurotoxic
NOEL/NOAEL:
Rat (2-generation feed) 30 mg kg1 d1
Glufosinate-ammonium [77182-82-2] Rat (teratogenicity, gavage) 1000 mg kg1 d1
Mammalian [13, 462, 552, 553]: (maternal and
developmental)
Rabbit (teratogenicity, gavage) 175 mg kg1 d1
LD50 (rat, oral) 4162000 mg/kg (maternal)
LD50 (mouse, oral) 416464 mg/kg Rabbit (teratogenicity, gavage) 350 mg kg1 d1
LD50 (dog, oral) > 200400 mg/kg (developmental)
LD50 (rat, i.p.) 83204 mg/kg Rat (2-year feed) 400 mg kg1 d1
LD50 (rat, dermal) ca. 4000 mg/kg Dog (1-year capsules) 500 mg kg1 d1
LD50 (rabbit, dermal) ca. 2000 mg/kg Mouse (2-year feed) 814 mg kg1 d1
LC50 (rat, 4-h inhalation) > 0.621 mg/L air (aerosol) ADI 0.3 mg kg1 d1
LC50 (rat, 4-h inhalation) 1.262.6 mg/L air (dust) ARfD 0.25 mg kg1 d1
Rabbit: nonirritating to skin AOEL 0.2 mg kg1 d1
Rabbit: slightly irritating to eyes
Vol. 39 Weed Control, 2. Individual Herbicides 349
LD50 (rat, dermal) > 5000 mg/kg
Ecological [13, 555]: LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 4.3 mg/L air
LD50 (bobwhite quail, oral) >3850 mg/kg NOEL/NOAEL:
LC50 (rainbow trout, 96-h) 8.2 mg/L Rat (2-year feed) ca. 5 mg kg1 d1
EC50 (daphnia magna, 48-h) 11 mg/L Mouse (2-year feed) ca. 14 mg kg1 d1
EC50 (algae, 72-h) 4.4 mg/L ADI 0.05 mg kg1 d1
LD50 (honeybee, oral) 100 mg/bee
LC50 (earthworm, 14-d) 480 mg/kg soil

Ecological [1, 2]:

Piperophos [24151-93-7] LD50 (Japanese quail, oral) 2970 mg/kg
Mammalian [1, 2, 556]: LC50 (salmon, 96-h) 2000 mg/L
EC50 (daphnia magna, 48-h) 4000 mg/L
EC50 (algae, 72-h) 38 mg/L
LD50 (rat, oral) 315335 mg/kg
LD50 (honeybee, contact) 16 mg/bee
LD50 (mouse, oral) 330410 mg/kg
LD50 (rat, dermal) > 2150 mg/kg
LC50 (rat, 1-h inhalation) > 1.96 mg/L air
Rabbit: nonirritating to skin
Rabbit: slightly irritating to eyes Butroxydim [138164-12-2]
Guinea pig: a skin sensitizer Mammalian [1, 2, 5]:
Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) 6.7 mg kg1 d1 LD50 (rat, oral) 16353476 mg/kg
(parental) LD50 (rat, dermal) > 2000 mg/kg
Rat (2-generation feed) > 65 mg kg1 d1 LC50 (rat, 4-h inhalation) > 2.99 mg/L air
(developmental) Rabbit: moderately irritating to skin
Rat (teratogenicity, gavage) 20 mg kg1 d1 Rabbit: mildly irritating to eyes
(maternal) Guinea pig: not a skin sensitizer
Rat (teratogenicity, gavage) > 20 mg kg1 d1 Nonmutagenic
(developmental) NOEL/NOAEL:
Rabbit (teratogenicity, gavage) 1 mg kg1 d1 Rat (teratogenicity, gavage) 5 mg kg1 d1
(maternal) (developmental)
Rabbit (teratogenicity, gavage) > 16 mg kg1 d1 Rabbit (teratogenicity, gavage) 15 mg kg1 d1
(developmental) (developmental)
Rat (2-year feed) 0.37 mg kg1 d1 Rat (2-year feed) 2.5 mg kg1 d1
Dog (1-year feed) 0.036 mg kg1 d1 Dog (1-year feed) 5 mg kg1 d1
Mouse (18-month feed) 27.6 mg kg1 d1 Mouse (2-year feed) 10 mg kg1 d1
ADI 0.001 mg kg1 d1 ADI 0.025 mg kg1 d1

Ecological [1, 2]: Ecological [1, 2, 5]:

LD50 (Japanese quail, oral) 11 929 mg/kg

LD50 (mallard duck, oral) 2000 mg/kg
LC50 (rainbow trout, 96-h) 6.0 mg/L
LC50 (rainbow trout, 96-h) 6.9 mg/L
EC50 (daphnia magna, 48-h) 0.0033 mg/L
EC50 (daphnia magna, 48-h) 3.7 mg/L
EC50 (algae, 72-h) 0.029 mg/L
EC50 (algae, 72-h) 0.71 mg/L
LD50 (honeybee, contact) 22 mg/bee
LD50 (honeybee, contact) 200 mg/bee
LC50 (earthworm, 14-d) 180 mg/kg oil
LC50 (earthworm, 14-d) 1000 mg/kg soil

2.14. Cyclohexene Oximes Clethodim [99129-21-2]

Mammalian [1, 2, 557, 558]:
Alloxydim-sodium [66003-55-2]
Mammalian [1, 2, 471]:
LD50 (rat, oral) 13601630 mg/kg
LD50 (mouse, oral) 24302570 mg/kg
LD50 (rat, oral) 22602322 mg/kg LD50 (rabbit, oral) > 2000 but mg/kg
LD50 (mouse, oral) 30004600 mg/kg < 5000
350 Weed Control, 2. Individual Herbicides Vol. 39
LD50 (rabbit, dermal) > 5000 mg/kg ADI 0.07 mg kg d1
1

LC50 (rat, 4-h inhalation) > 3.9 mg/L air ARfD 1 mg kg1 d1
Rabbit: slightly irritating AOEL 0.1 mg kg1 d1
to skin and eyes
Guinea pig: not a skin sensitizer
Nonmutagenic
NOEL/NOAEL:
Rat (2-generation feed) 39 mg kg1 d1
Ecological [1, 2]:
(parental)
> 190 mg kg1 d1 LD50 (bobwhite quail, oral) 2000 mg/kg
(developmental) LC50 (rainbow trout, 96-h) 215 mg/L
Rat (teratogenicity, gavage) 100 mg kg1 d1 EC50 (daphnia magna, 48-h) 71 mg/L
(maternal and EC50 (algae, 72-h) 38 mg/L
developmental) LD50 (honeybee, contact) 100 mg/bee
Rabbit (teratogenicity, gavage) 25 mg kg1 d1 LC50 (earthworm, 14-d) 1000 mg/kg soil
(maternal)
Rabbit (teratogenicity, gavage) > 300 mg kg1 d1
(developmental)
Rat (2-year feed) 16 mg kg1 d1 Profoxydim [139001-49-3]
Dog (1-year capsule) 1 mg kg1 d1
Mouse (18-month feed) 30 mg kg1 d1
Mammalian [2, 560]:
ADI 0.01 mg kg1 d1
AOEL 0.21 mg kg1 d1 LD50 (rat, oral) 5000 mg/kg
LD50 (rat, dermal) 4000 mg/kg
LC50 (rat, 4-h inhalation) >5.2 mg/L air
NOEL/NOAEL:
Ecological [1, 2]: Rat (2-year feed) 5 mg kg1 d1
ADI 0.05 mg kg1 d1

LD50 (bobwhite quail, oral) 1640 mg/kg

LC50 (salmon, 96-h) 25 mg/L
EC50 (daphnia magna, 48-h) 100 mg/L Ecological [2]:
EC50 (algae, 72-h) 12 mg/L
LD50 (honeybee, oral) 43 mg/bee
LC50 (earthworm, 14-d) 454 mg/kg soil LD50 (bobwhite quail, oral) >2000 mg/kg
LC50 (rainbow trout, 96-h) 15 mg/L
EC50 (daphnia magna, 48-h) 18 mg/L
EC50 (algae, 72-h) 33 mg/L
LD50 (honeybee, oral) >200 mg/bee
Cycloxydim [101205-02-1] LC50 (earthworm, 14-d) 1000 mg/kg/soil
Mammalian [1, 2, 559]:

LD50 (rat, oral) 38305000 mg/kg

LD50 (mouse, oral) > 5000 mg/kg Sethoxydim [74051-80-2]
LD50 (rat, dermal) > 2000 mg/kg Mammalian [13, 349, 561]:
LC50 (rat, 4-h inhalation) > 5.28 mg/L air
Rabbit: irritating to skin and eyes
Guinea pig: not a skin sensitizer LD50 (rat, oral) 26763500 mg/kg
Nonmutagenic LD50 (mouse, oral) 56006300 mg/kg
NOEL/NOAEL: LD50 (rat, dermal) > 5000 mg/kg
Rat (multigeneration, 10 mg kg1 d1 LD50 (mouse, dermal) > 5000 mg/kg
drinking water) (parental) LC50 (rat, 4-h inhalation) > 6.28 mg/L air
38 mg kg1 d1 Rabbit: nonirritating to skin
(developmental) Rabbit: eye irritant
Rat (teratogenicity, gavage) 200 mg kg1 d1 Guinea pig: a skin sensitizer
(maternal and Nonmutagenic
developmental) NOEL/NOAEL:
Rabbit (teratogenicity, gavage) 100 mg kg1 d1 Rat (teratogenicity, gavage) > 250 mg kg1 d1
(maternal) (developmental)
Rabbit (teratogenicity, gavage) 200 mg kg1 d1 Rabbit (teratogenicity, gavage) 160 mg kg1 d1
(developmental) (maternal and
Rat (2-year, water) 7 mg kg1 d1 developmental)
Dog (1-year feed) 20 mg kg1 d1 Rat (2-year feed) 17.2 mg kg1 d1
Mouse (2-year water) > 32 mg kg1 d1 Dog (1-year feed) 8.9 mg kg1 d1
Vol. 39 Weed Control, 2. Individual Herbicides 351
1 1
Mouse (2-year feed) 18 mg kg d LD50 (rat, dermal) > 2000 mg/kg
ADI 0.14 mg kg1 d1 LC50 (rat, 4-h inhalation) > 3.5 mg/L air
Rabbit: mildly irritating
to skin and eyes
Guinea pig: not a skin sensitizer
Nonmutagenic
Ecological [13]: NOEL/NOAEL:
Rat (90-day feed) ca. 0.8 mg kg1 d1
LD50 (mallard duck, oral) 2510 mg/kg Dog (90-day feed) ca. 0.125 mg kg1 d1
LC50 (rainbow trout, 96-h) 170 mg/L ADI/AOEL 0.005 mg kg1 d1
EC50 (daphnia magna, 48-h) 1.5 mg/L ARfD 0.01 mg kg1 d1
EC50 (algae, 72-h) 0.64 mg/L
LD50 (honeybee, contact) 10 mg/bee
LC50 (earthworm, 14-d) 542 mg/kg soil
Ecological [13]:

LD50 (mallard duck, oral) >3020 mg/kg

Tepraloxydim [149979-41-9] LC50 (bluegill sunfish, 96-h) 6.1 mg/L
Mammalian [1, 2, 349, 562]: EC50 (daphnia magna, 48-h) 175 mg/L
EC50 (algae, 72-h) 5.1 mg/L
LD50 (honeybee, contact) 100 mg/bee
LD50 (rat, oral) 2000 mg/kg LC50 (earthworm, 14-d) 1000 mg/kg soil
LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 5.1 mg/L air
Rabbit: eye irritant
Rabbit: not a skin irritant
Nonmutagenic 2.15. (Benzo)nitriles
NOEL/NOAEL:
Rat (1-year feed) 538 mg kg1 d1 Bromoxynil [1689-84-5]
Dog (1-year feed) 11.512.5 mg kg1 d1
Mouse (78-week feed) 37-52 mg kg1 d1
Mammalian [13, 353, 462, 466]:
Rat (2-generation feed) 50.655 mg kg1 d1
(parental) LD50 (rat, oral) 81440 mg/kg
Rat (2-generation feed) 260 mg kg1 d1 LD50 (mouse, oral) 160 mg/kg
(developmental) LD50 (rabbit, oral) 335 mg/kg
Rabbit (teratogenicity, gavage) 60 mg kg1 d1 LD50 (dog, oral) ca. 100 mg/kg
(maternal) LD50 (rat, dermal) > 3660 mg/kg
Rabbit (teratogenicity, gavage) 180 mg kg1 d1 LD50 (rabbit, dermal) 3660 mg/kg
(developmental) LC50 (rat, 4-h inhalation) 0.15 mg/L air
ADI 0.025 mg kg1 d1 Rabbit: mildly irritating
ARfD 0.4 mg kg1 d1 to skin and eyes
AOEL 0.06 mg kg1 d1 Guinea pig: not a skin sensitizer
RfD 0.05 mg kg1 d1 Nonmutagenic
NOEL/NOAEL:
Dog (1-year capsules) 0.3 mg kg1 d1
Rat (2-year feed) 3 mg kg1 d1
Ecological [1, 2]: Mouse (78-week feed) 3 mg kg1 d1
Rat (3-generation feed) 15 mg kg1 d1
ADI/AOEL 0.01 mg kg1 d1
LD50 (pheasant, oral) 2000 mg/kg ARfD 0.04 mg kg1 d1
LC50 (rainbow trout, 96-h) 100 mg/L RfD 0.02 mg kg1 d1
EC50 (daphnia magna, 48-h) 7.44 mg/L
EC50 (algae, 72-h) 78 mg/L
LD50 (honeybee, oral) 25 mg/bee
LC50 (earthworm, 14-d) 100 mg/kg soil
Ecological [13]:

LD50 (bobwhite quail, oral) 217 mg/kg

Tralkoxydim [87820-88-0] [13, 351]: LC50 (bluegill sunfish, 96-h) 29.2 mg/L
EC50 (daphnia magna, 48-h) 12.5 mg/L
EC50 (algae, 72-h) 0.12 mg/L
LD50 (rat, oral) 9341324 mg/kg LD50 (honeybee, oral) 5 mg/bee
LD50 (mouse, oral) 11001231 mg/kg LC50 (earthworm, 14-d) 45 mg/kg soil
LD50 (rabbit, oral) > 519 mg/kg
352 Weed Control, 2. Individual Herbicides Vol. 39

Dichlobenil [1194-65-6] Ecological [2, 356]:

Mammalian [13, 462]:
LD50 (bobwhite quail, oral) 62 mg/kg
LD50 (rat, oral) 4460 mg/kg LC50 (rainbow trout, 96-h) 8.5 mg/L
LD50 (mouse, oral) 10141621 mg/kg EC50 (daphnia magna, 48-h) 3.9 mg/L
LD50 (rat, dermal) > 1000 mg/kg EC50 (algae, 72-h) 24 mg/L
LD50 (rabbit, dermal) > 2000 mg/kg LD50 (honeybee, oral) 10 mg/bee
LC50 (rat, 4-h inhalation) > 0.25 mg/L air LC50 (earthworm, 14-d) 60 mg/kg soil
Rabbit: nonirritating to skin
Rabbit: eye irritant
Guinea pig: not a skin sensitizer
Nonmutagenic Pyraclonil [158353-15-2]
NOEL/NOAEL:
Rat (2-generation feed) ca. 3 mg kg1 d1
Mammalian [2, 358, 503]:
(parental)
Rat (teratogenicity, gavage) 180 mg kg1 d1 LD50 (rat, oral 11304980 mg/kg
Rabbit (teratogenicity, gavage) 45 mg kg1 d1 LD50 (mouse, oral) 8811040 mg/kg
(maternal and LD50 (rat, dermal) >2000 mg/kg
developmental) LC50 (rat, 4-h inhalation) 4.97 mg/L air
Rat (2-year feed) ca. 2.5 mg kg1 d1 Rabbit: slightly irritating
Dog (1-year feed) ca. 1.25 mg kg1 d1 to skin and eyes
Hamster (20-month feed) ca. 10 mg kg1 d1 Guinea pig: not a sensitizer
ADI 0.025 mg kg1 d1 Nonmutagenic
RfD 0.0005 mg kg1 d1 NOEL/NOAEL:
Rat (2-year feed) 0.44 mg kg1 d1
Mouse (78-week feed) 8.6 mg kg1 d1
Dog (1-year feed) 5 mg kg1 d1
Ecological [13]: Rat (2-generation feed) 26 mg kg1 d1
(parental)
Rat (2-generation feed) 225 mg kg1 d1
LD50 (bobwhite quail, oral) 683 mg/kg (developmental)
LC50 (fish, 96-h) 5 mg/L Rat (teratogenicity, gavage) 26 mg kg1 d1
EC50 (daphnia magna, 48-h) 6.2 mg/L (maternal)
EC50 (algae, 72-h) 2.7 mg/L Rat (teratogenicity, gavage) 225 mg kg1 d1
LD50 (honeybee, contact) 11 mg/bee (developmental)
LC50 (earthworm, 14-d) 1000 mg/kg soil Rabbit (teratogenicity, gavage) 3 mg kg1 d1
(maternal)
Rabbit (teratogenicity, gavage) 24 mg kg1 d1
(developmental)
ADI 0.0044 mg kg1 d1
Ioxynil [1689-83-4]
Mammalian [13, 356, 462]:

LD50 (rat, oral) 110130 mg/kg Ecological [2, 358]:

LD50 (mouse, oral) 230 mg/kg
LD50 (rat, dermal) 1050> 2000 mg/kg
LD50 (rabbit, dermal) 1050 mg/kg LC50 (carp, 96-h) 28 mg/L
LC50 (rat, 6-h inhalation) 0.4 mg/L air EC50 (daphnia magna, 48-h) 16.3 mg/L
Rabbit: nonirritating to skin EC50 (algae, 72-h) 3.8 mg/L
Rabbit: eye irritant
Guinea pig: not a skin sensitizer
Nonmutagenic
NOEL/NOAEL: 2.16. Triazinones
Rat (2-generation feed) > 10 mg kg1 d1
Rat (teratogenicity, gavage) 5 mg kg1 d1
Rabbit (teratogenicity, gavage) 15 mg kg1 d1 Hexazinone [51235-04-2]
Rat (2-year feed) 0.5 mg kg1 d1 Mammalian [1, 2, 462, 563]:
Dog (30-week feed) 1 mg kg1 d1
Mouse (18-month feed) < 1.5 mg kg1 d1
ADI 0.005 mg kg1 d1 LD50 (rat, oral) 1690 mg/kg
ARfD 0.04 mg kg1 d1 LD50 (guinea pig, oral) 860 mg/kg
AOEL 0.01 mg kg1 d1 LD50 (rabbit, dermal) 500 mg/kg
LC50 (rat, 1-h inhalation) > 7.48 mg/L air
Vol. 39 Weed Control, 2. Individual Herbicides 353
Rabbit: irritating to
skin and eyes
Metribuzin [21087-64-9]
Guinea pig: not Mammalian [13, 360, 462]:
a skin sensitizer
Nonmutagenic
LD50 (rat, oral) 10901206 mg/kg
NOEL/NOAEL:
LD50 (mouse, oral) ca. 700 mg/kg
Rat (3-generation feed) ca. 10 mg kg1 d1
LD50 (guinea pig, oral) 245274 mg/kg
Rat (teratogenicity, gavage) 100 mg kg1 d1
LD50 (rabbit, dermal) > 20 000 mg/kg
(maternal and
LC50 (rat, 4-h inhalation) > 0.65 mg/L air
developmental)
Rabbit: nonirritating
Rabbit (teratogenicity, gavage) 50 mg kg1 d1
to skin and eyes
(maternal and
Guinea pig: not
developmental)
a skin sensitizer
Rat (2-year feed) ca. 10 mg kg1 d1
Nonmutagenic
Dog (1-year feed) ca. 5 mg kg1 d1
NOEL/NOAEL:
Mouse (2-year feed) ca. 30 mg kg1 d1
Rat (3-generation feed) ca. 2 mg kg1 d1
ADI 0.05 mg kg1 d1
(parental)
20 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) ca. < 25 mg kg1 d1
Ecological [1, 2]: (maternal)
Rat (teratogenicity, gavage) 25 mg kg1 d1
(developmental)
LD50 (bobwhite quail, oral) 2258 mg/kg Rabbit (teratogenicity, gavage) 15 mg kg1 d1
LC50 (rainbow trout, 96-h) 320 mg/L (maternal and
EC50 (daphnia magna, 48-h) 85 mg/L developmental)
EC50 (algae, 72-h) 0.0145 mg/L Rabbit (teratogenicity, > 135 mg kg1 d1
LD50 (honeybee) 60 mg/bee gavage)
Rat (2-year feed) ca. 5 mg kg1 d1
Dog (2-year feed) ca. 2.8 mg kg1 d1
Mouse (18-month feed) ca. 114 mg kg1 d1
ADI 0.013 mg kg1 d1
Metamitron [41394-05-2] ARfD/AOEL 0.02 mg kg1 d1
Mammalian [1, 2, 360]:

LD50 (rat, oral) ca. 1200 mg/kg Ecological [13, 362]:

LD50 (mouse, oral) ca. 650 mg/kg
LD50 (dog, oral) > 1000 mg/kg
LD50 (rat, dermal) > 4000 mg/kg LD50 (bobwhite quail, oral) 164 mg/kg
LC50 (rat, 4-h inhalation) 3.17 mg/L air LC50 (rainbow trout, 96-h) 75 mg/L
Rabbit: nonirritating EC50 (daphnia magna, 48-h) 49 mg/L
to skin and eyes EC50 (algae, 72-h) 0.02 mg/L
Guinea pig: not a sensitizer LD50 (honeybee, oral) 53 mg/bee
NOEL/NOAEL: LC50 (earthworm, 14-d) 427 mg/kg soil
Rat (2-year feed) 56 mg kg1 d1
Dog (2-year feed) ca. 2.5 mg kg1 d1
Mouse (87-week feed) ca. 8 mg kg1 d1
ADI 0.03 mg kg1 d1
ARfD 0.1 mg kg1 d1 2.17. Amides
AOEL 0.036 mg kg1 d1
Allidochlor [93-71-0]
Mammalian [2, 364]:
Ecological [1, 2, 360]:
LD50 (rat, oral) 290700 mg/kg
LD50 (Japanese quail, oral) 1302 mg/kg LD50 (rabbit, dermal) 830 mg/kg
LC50 (rainbow trout, 96-h) 190 mg/L Rabbit: skin and eye irritant
EC50 (daphnia magna, 48-h) 5.7 mg/L Guinea pig: skin sensitizer
EC50 (algae, 72-h) 0.4 mg/L NOEL/NOAEL:
LD50 (honeybee, oral) 97 mg/bee Rat (90-day feed) 10 mg kg1 d1
LC50 (earthworm, 14-d) 914 mg/kg soil Dog (90-day feed) 5 mg kg1 d1
354 Weed Control, 2. Individual Herbicides Vol. 39

Ecological [2, 364, 480]: Ecological [564]:

LC50 (bobwhite quail, 8-d diet) >10 000 ppm LC50 (fish, 48-h) >10 mg/L
LC50 (rainbow trout, 96-h) 2 mg/L EC50 (daphnia magna, 48-h) >10 mg/L
EC50 (algae, 72-h) 10 mg/L EC50 (algae, 24-h) >25 mg/L

Dimethenamid [87674-68-8]
Beflubutamid [113614-08-7]
Mammalian [1, 2, 367, 462]:
Mammalian [2, 366]:
LD50 (rat, oral) 13002140 mg/kg
LD50 (rat, oral) >5000 mg/kg LD50 (rat, dermal) > 2000 mg/kg
LD50 (rat, dermal) >2000 mg/kg LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) 5.0 mg/L air LC50 (rat, 4-h inhalation) >4.9 mg/L air
Rabbit: nonirritating to skin and eyes Rabbit: slightly irritating to skin
Guinea pig: not a sensitizer Rabbit: mildly irritating to eyes
Nonmutagenic Guinea pig: not a skin sensitizer
NOEL/NOAEL: Nonmutagenic
Rat (2-generation feed) 17 mg kg1 d1 NOEL/NOAEL:
(parental and Rat (2-generation feed) 10 mg kg1 d1
developmental) (parental)
Rabbit (teratogenicity, gavage) 100 mg kg1 d1 Rat (2-generation feed) 25 mg kg1 d1
(maternal and (developmental)
developmental) Rat (teratogenicity, gavage) 50 mg kg1 d1
Rat (2-year feed) 2.2 mg kg1 d1 (maternal)
ADI 0.02 mg kg1 d1 Rat (teratogenicity, gavage) 215 mg kg1 d1
(developmental)
Rabbit (teratogenicity, gavage) 37.5 mg kg1 d1
(maternal)
Ecological [2, 366]: Rabbit (teratogenicity, gavage) 75 mg kg1 d1
(developmental)
Rat (2-year feed) 6 mg kg1 d1
LD50 (mallard duck, oral) 2000 mg/kg Dog (1-year feed) 9.6 mg kg1 d1
LC50 (rainbow trout, 96-h) 1.9 mg/L Mouse (18-month feed) 4.5 mg kg1 d1
EC50 (daphnia magna, 48-h) 1.64 mg/L ADI 0.02 mg kg1 d1
EC50 (algae, 72-h) 0.00445 mg/L ARfD 0.25 mg kg1 d1
LD50 (honeybee, oral) 100 mg/bee AOEL 0.04 mg kg1 d1
LC50 (earthworm, 14-d) 732 mg/kg soil RfD 0.05 mg kg1 d1

Bromobutide [74712-19-9] Ecological [1, 2, 367]:

Mammalian [2, 564]:
LD50 (bobwhite quail, oral) 1068 mg/kg
LC50 (rainbow trout, 96-h) 6.3 mg/L
LD50 (rat, oral) >5000 mg/kg EC50 (daphnia magna, 48-h) 48 mg/L
LD50 (rat, dermal) >5000 mg/kg EC50 (algae, 72-h) 0.017 mg/L
LD50 (mouse, oral) >5000 mg/kg LD50 (honeybee, oral) 134 mg/bee
LC50 (rat, 4-h inhalation) 0.327 mg/L air LC50 (earthworm, 14-d) 295 mg/kg soil
Rabbit: skin and eye irritant
Nonmutagenic
NOEL/NOAEL:
Rat (2-year feed) 1.732.07 mg kg1 d1
Mouse (18-month feed) 20.9107 mg kg1 d1 Dimethenamid-P [163515-14-8]
Rat (teratogenicity, gavage) 1000 mg kg1 d1 Mammalian [1, 2, 369]:
(maternal and
developmental)
Rat (2-generation feed) 90 mg kg1 d1 LD50 (rat, oral) 429 mg/kg
(parental and LD50 (rat, dermal) >2000 mg/kg
developmental) LC50 (rat, 4-h inhalation 2.2 mg/L air
ADI 0.04 mg kg1 d1 Rabbit: irritating to skin and eyes
Guinea pig: a sensitizer
Vol. 39 Weed Control, 2. Individual Herbicides 355
Nonmutagenic Rabbit: nonirritating to skin and eyes
NOEL/NOAEL: Guinea pig: not a sensitizer
Rat (2-year feed) 5 mg kg1 d1 Nonmutagenic
Mouse (94-week feed) 3.8 mg kg1 d1 NOEL/NOAEL:
Rat (2-generation feed) 36 mg kg1 d1 ADI 0.0052 mg kg1 d1
Rat (teratogenicity, gavage) 50 mg kg1 d1
ADI 0.02 mg kg1 d1
ARfD 0.25 mg kg1 d1
AOEL 0.04 mg kg1 d1 Ecological [2]:

LD50 (Japanese quail, oral) 2000 mg/kg

LC50 (rainbow trout, 96-h) 3.4 mg/L
Ecological [1, 2, 369]: EC50 (daphnia magna, 48-h) 10 mg/L
EC50 (algae, 72-h) 0.006 mg/L
LD50 (mallard duck, oral) 1908 mg/kg LD50 (honeybee, contact) 150 mg/bee
LC50 (rainbow trout, 96-h) 2.6 mg/L LC50 (earthworm, 14-d) 1000 mg/kg soil
EC50 (daphnia magna, 48-h) 12 mg/L
EC50 (algae, 72-h) 0.062 mg/L
LD50 (honeybee, contact) 94 mg/bee
LC50 (earthworm, 14-d) 147 mg/kg soil Napropamide [15299-99-7]
Mammalian [13, 5, 371, 466]:

Diphenamid [957-51-7] LD50 (rat, oral) 4680 mg/kg

Mammalian [13, 464, 565]: LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 4.8 mg/L air
Rabbit: mildly irritating
LD50 (rat, oral) 1050 mg/kg
to skin and eyes
LD50 (rat, dermal) >2250 mg/kg
Nonmutagenic
LD50 (rabbit, oral) 1500 mg/kg
NOEL/NOAEL:
LC50 (rat, 4-h inhalation) 0.9 mg/L
Rat (2-year feed) 12.5 mg kg1 d1
Rabbit: nonirritating
Dog (1-year capsules) 50 mg kg1 d1
to skin and eyes
Mouse (18-month feed) 67.5 mg kg1 d1
Guinea pig: not a sensitizer
Rat (3-generation feed) 30 mg kg1 d1
Nonmutagenic
(parental)
NOEL/NOAEL:
Rat (3-generation feed) 100 mg kg1 d1
Rat (2-year feed) 10 mg kg1 d1
(developmental)
Dog (2-year capsules) 3 mg kg1 d1
ADI 0.3 mg kg1 d1
Rat (3-generation feed) 10 mg kg1 d1
AOEL 0.5 mg kg1 d1
(parental)
RfD 0.1 mg kg1 d1
Rat (3-generation feed) 30 mg kg1 d1
(developmental)
RfD 0.03 mg kg1 d1

Ecological [13, 5, 371]:

Ecological [13, 565]:
LD50 (mallard duck, oral) 2250 mg/kg
LC50 (rainbow trout, 96-h) 6.6 mg/L
LD50 (mallard duck, oral) 30 000 mg/kg LC50 (daphnia magna, 48-h) 14.3 mg/L
LC50 (rainbow trout, 96-h) 97 mg/L EC50 (algae, 72-h) 3.4 mg/L
EC50 (daphnia magna, 48-h) 0.058 mg/L LD50 (honeybee, oral) 100 mg/bee
LD50 (honeybee, contact) 2432 mg/bee LC50 (earthworm, 14-d) 564 mg/kg soil

Fentrazamide [158237-07-1] Naptalam [132-66-1]

Mammalian [2, 503]: Mammalian [13, 373]:

LD50 (rat, oral) >5000 mg/kg LD50 (rat, oral) 17708192 mg/kg
LD50 (mouse, oral) >5000 mg/kg LD50 (rat, dermal) >2000 mg/kg
LD50 (rat, dermal) >5000 mg/kg LC50 (rat, 4-h inhalation) 2.07 mg/L air
LC50 (rat, 4-h inhalation) >5.085 mg/L air Rabbit: slight eye irritant
356 Weed Control, 2. Individual Herbicides Vol. 39
Rabbit: not a skin irritant
Guinea pig: a sensitizer
Ecological [2, 374]:
Nonmutagenic
NOEL/NOAEL: LD50 (mallard duck, oral) 1800 mg/kg
Rat (2-year feed) 140 mg kg1 d1 LC50 (rainbow trout, 96-h) 2.2 mg/L
Mouse (18-month feed) 89 mg kg1 d1 EC50 (daphnia magna, 48-h) 23
Dog (1-year feed) 25.8 mg kg1 d1 EC50 (algae, 72-h) 9.4 mg/L
Rat (2-generation feed) 30 mg kg1 d1 LD50 (honeybee, oral) 200 mg/bee
(parental and LC50 (earthworm, 14-d) 527 mg/kg soil
developmental)
Rat (teratogenicity, gavage) 15 mg kg1 d1
(maternal)
Rat (teratogenicity, gavage) 115 mg kg1 d1 Propyzamide [23950-58-5]
(developmental)
Rabbit (teratogenicity, gavage) 200 mg kg1 d1
Mammalian [13, 375]:
(maternal and
developmental) LD50 (rat, oral) >2000 mg/kg
ADI 0.05 mg kg1 d1 LD50 (rat, dermal) >2000 mg/kg
RfD 0.258 mg kg1 d1 LC50 (rat, 4-h inhalation) 2.1 mg/L air
Rabbit: nonirritating to skin and eyes
Guinea pig: not a sensitizer
NOEL/NOAEL:
Ecological [13]: Rat (2-year feed) 10 mg kg1 d1
Dog (1-year feed) 8 mg kg1 d1
Mouse (18-month feed) 2 mg kg1 d1
Rat (2-generation feed) 10 mg kg1 d1
LD50 (mallard duck, oral) 4640 mg/kg
(parental and
LC50 (rainbow trout, 96-h) 76 mg/L
developmental)
EC50 (daphnia magna, 48-h) 119 mg/L
ADI 0.01 mg kg1 d1
LD50 (honeybee, contact) 113 mg/bee
ARfD 0.02 mg kg1 d1
AOEL 0.08 mg kg1 d1

Pethoxamid [106700-29-2]
Mammalian [2, 374]: Ecological [13, 375]:

LD50 (mallard duck, oral) >10 000 mg/kg

LD50 (rat, oral) 983 mg/kg LC50 (rainbow trout, 96-h) 4.7 mg/L
LD50 (rat, dermal) >2000 mg/kg EC50 (daphnia magna, 48-h) 5.6 mg/L
LC50 (rat, 4-h inhalation) 4.18 mg/L air EC50 (algae, 72-h) 2.8 mg/L
Rabbit: nonirritating LD50 (honeybee, contact) 136 mg/bee
to skin and eyes LC50 (earthworm, 14-d) 173 mg/kg soil
Guinea pig: a sensitizer
Nonmutagenic
NOEL/NOAEL:
Dog (1-year feed) 2 mg kg1 d1
Rat (2-year feed) 1 mg kg1 d1 Tebutam (Butam) [35256-85-0]
Mouse (18-month feed) 4 mg kg1 d1 Mammalian [1, 2, 461]:
Rat (2-generation feed) 14 mg kg1 d1
(parental)
Rat (2-generation feed) 112 mg kg1 d1 LD50 (rat, oral) 6210 mg/kg
(developmental) LD50 (rabbit, dermal) >2000 mg/kg
Rat (teratogenicity, gavage) 8 mg kg1 d1 LC50 (rat, 4-h inhalation) >14.4 mg/L air
(maternal) NOEL/NOAEL:
Rat (teratogenicity, gavage) 600 mg kg1 d1 Rat (90-d feed) 300 mg kg1 d1
(developmental) ADI 0.150.3 mg kg1 d1
Rabbit (teratogenicity, gavage) 50 mg kg1 d1
(maternal)
Rabbit (teratogenicity, gavage) 200 mg kg1 d1
(developmental) Ecological [1, 2]:
ADI 0.01 mg kg1 d1
ARfD 0.08 mg kg1 d1
AOEL 0.02 mg kg1 d1 LD50 (mallard duck, oral) 5000 mg/kg
LC50 (rainbow trout, 96-h) 19 mg/L
Vol. 39 Weed Control, 2. Individual Herbicides 357
EC50 (daphnia magna, 48-h) 5.6 mg/L
EC50 (algae, 72-h) 82 mg/L
Ecological [2, 376, 377]:
LD50 (honeybee, oral) 100 mg/bee
LC50 (earthworm, 14-d) 200 mg/kg soil LD50 (bobwhite quail, oral) 1608 mg/kg
LC50 (bluegill sunfish, 96-h) 2.13 mg/L
EC50 (daphnia magna, 48-h) 31 mg/L
EC50 (algae, 72-h) 0.00204 mg/L
LD50 (honeybee, oral) 170 mg/bee
2.18. Anilides LC50 (earthworm, 14-d) 219 mg/kg soil

Flamprop [58667-63-3]
Mammalian [1, 2, 471]:
Mefenacet [73250-68-7]
LD50 (rat, oral) 4000 mg/kg
Mammalian [1, 2]:
LD50 (rat, dermal) >2000 mg/kg
NOEL/NOAEL: LD50 (rat, oral) >5000 mg/kg
Rat (2-year feed) 0.125 mg kg1 d1 LD50 (rat, dermal) >5000 mg/kg
Dog (2-year feed) 0.225 mg kg1 d1 LC50 (rat, 4-h inhalation) 0.02 mg/L air
ADI 0.001 mg kg1 d1 NOEL/NOAEL:
Rat (2-year feed) 5 mg kg1 d1
ADI 0.0036 mg kg1 d1

Ecological [1, 2]:

Ecological [1, 2]:
LD50 (mallard duck, oral) >2000 mg/kg
LC50 (rainbow trout, 96-h) 2.4 mg/L
EC50 (daphnia magna, 48-h) 12 mg/L LD50 (bobwhite quail, oral) 5000 mg/kg
EC50 (algae, 72-h) 7 mg/L LC50 (salmon, 96-h) 6 mg/L
LD50 (honeybee) 50 mg/bee EC50 (daphnia magna, 48-h) 1.8 mg/L
LC50 (earthworm, 14-d) 1000 mg/kg soil EC50 (algae, 72-h) 0.18 mg/L
LC50 (earthworm, 14-d) 1000 mg/kg soil

Flufenacet [142459-58-3]
Mammalian [2, 376, 377, 566]: Mefluidide [53780-34-0]
Mammalian [1, 2, 379, 495]:
LD50 (rat, oral) 5891617 mg/kg
LD50 (mouse, oral) 13311756 mg/kg LD50 (rat, oral) >4000 mg/kg
LD50 (rabbit, dermal) >2000 mg/kg LD50 (rabbit, dermal) >4000 mg/kg
LC50 (rat, 4-h inhalation) 3.74 mg/L air LD50 (mouse, oral) 8301920 mg/kg
Rabbit: skin and eye irritant LC50 (rat, 4-h inhalation) >5.4 mg/L air
Guinea pig: not a sensitizer Rabbit: minimally irritating eyes
Nonmutagenic Rabbit: nonirritating to skin
NOEL/NOAEL: Guinea pig: not a sensitizer
Rat (teratogenicity, gavage) 25 mg kg1 d1 Nonmutagenic
(maternal and NOEL/NOAEL:
developmental) Rat (2-year feed) <30 mg kg1 d1
Rabbit (teratogenicity, gavage) 5 mg kg1 d1 Mouse (84-week feed) 90 mg kg1 d1
(maternal) Dog (1-year feed) 1.5 mg kg1 d1
Rabbit (teratogenicity, gavage) 25 mg kg1 d1 Rat (3-generation feed) 102183 mg kg1 d1
(developmental) (parental and
Rat (2-generation feed) 1.41.5 mg kg1 d1 developmental)
(parental and Rat (teratogenicity, gavage) 58 mg kg1 d1
developmental) (maternal and
Dog (1-year feed) 1.141.29 mg kg1 d1 developmental)
Rat (2-year feed) 1.2 mg kg1 d1 Rabbit (teratogenicity, gavage) 60 mg kg1 d1
Mouse (78-week feed) 7.49.4 mg kg1 d1 (maternal and
ADI 0.005 mg kg1 d1 developmental)
ARfD/AOEL 0.017 mg kg1 d1 RfD 0.015 mg kg1 d1
RfD 0.004 mg kg1 d1 ARfD 0.58 mg kg1 d1
358 Weed Control, 2. Individual Herbicides Vol. 39
LC50 (rat, 4-h inhalation) >6.9 mg/L air
Ecological [1, 2, 379]: Rabbit: nonirritating
to skin and eyes
LD50 (mallard duck, oral) 4620 mg/kg Guinea pig: not a sensitizer
LC50 (rainbow trout, 96-h) 100 mg/L Nonmutagenic
EC50 (daphnia magna, 48-h) 103 mg/L NOEL/NOAEL:
EC50 (algae, 72-h) 0.75 mg/L Rat (2-generation feed) 35 mg kg1 d1
LD50 (honeybee) 25 mg/bee (parental)
Rat (2-generation feed) 144 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) 100 mg kg1 d1
Perfluidone [37924-13-3] (maternal and
Mammalian [2, 380, 471, 566]: developmental)
Rabbit (teratogenicity, gavage) 120 mg kg1 d1
LD50 (rabbit, dermal) >4000 mg/kg (maternal and
Rabbit: not a skin irritant developmental)
Rabbit: moderately irritating to eyes Dog (1-year feed) 50 mg/kg//d
NOEL/NOAEL: Mouse (2-year feed) 4967 mg kg1 d1
RfD (US-EPA) 0.01 mg kg1 d1 Rat (2-year feed) 145236 mg kg1 d1
ADI 0.003 mg kg1 d1 ADI 0.35 mg kg1 d1

Ecological [2]: Ecological [2]:

LC50 (rainbow trout, 96-h) 17 mg/L LC50 (rainbow trout, 96-h) 124 mg/L
EC50 (daphnia magna, 48-h) 122 mg/L
EC50 (algae, 72-h) 0.02 mg/L

Propanil [709-98-8]
Mammalian [2, 3, 5, 381, 382]:
2.19. Benzoic Acids
LD50 (rat, oral) 1080 mg/kg
LD50 (rabbit, dermal) >2000 mg/kg Bispyribac-sodium [125401-92-5] [Mam-
LC50 (rat, 4-h inhalation) >6.1 mg/L air malian [1, 2, 5]:
Rabbit: moderate eye irritant
Rabbit: slightly irritating to skin
Guinea pig: not a sensitizer LD50 (rat, oral) 26354111 mg/kg
Nonmutagenic LD50 (rat, dermal) > 2000 mg/kg
NOEL/NOAEL: LC50 (rat, 4-h inhalation) > 4.48 mg/L air
Rat (2-year feed) 20 mg kg1 d1 Rabbit: nonirritating to skin
Dog (2-year feed) 15 mg kg1 d1 Rabbit: slightly irritating to eyes
Rat (3-generation feed) 15 mg kg1 d1 Nonmutagenic
Rat (teratogenicity, gavage) 20 mg kg1 d1 NOEL/NOAEL:
ADI/RfD 0.005 mg kg1 d1 Dog (52-week capsules) 10 mg kg1 d1
Rat (2-year feed) 10 mg kg1 d1
Mouse (2-year feed) 15 mg kg1 d1
Rat (2-generation feed) 1 mg kg1 d1
Ecological [2, 3, 5]: (parental)
Rat (2-generation feed) 50 mg kg1 d1
(developmental)
LD50 (mallard duck, oral) 196 mg/kg
ADI 0.072 mg kg1 d1
LC50 (rainbow trout, 96-h) 2.3 mg/L
EC50 (daphnia magna, 48-h) 4.8 mg/L
EC50 (algae, 72-h) 0.05 mg/L
LD50 (honeybee, contact) 240 mg/bee Ecological [1, 2, 5]:

LD50 (bobwhite quail, oral) 2250 mg/kg

Pyrimisulfan [221205-90-9] LC50 (rainbow trout, 96-h) 95 mg/L
Mammalian [2, 509]: EC50 (daphnia magna, 48-h) 95 mg/L
EC50 (algae, 72-h) 3.2 mg/L
LD50 (honeybee, oral) 141 mg/bee
LD50 (rat, oral) 3002 mg/kg LC50 (earthworm, 14-d) 1000 mg/kg soil
LD50 (rat, dermal) >2000 mg/kg
Vol. 39 Weed Control, 2. Individual Herbicides 359
EC50 (daphnia magna, 48-h) 4.6 mg/L
Chloramben (Amben) [133-90-4] EC50 (algae, 72-h) 10 mg/L
Mammalian [13, 5, 467, 567]: Toxic to bee

LD50 (rat, oral) >5000 mg/kg

LD50 (rabbit, dermal) >2000 mg/kg
Rabbit: mild skin irritant Dicamba [1918-00-9]
Rabbit: moderately irritant to eyes
Guinea pig: moderate sensitizer
Mammalian [1, 2, 385, 386, 462]:
NOEL/NOAEL:
Rat (2-year feed) 500919 mg kg1 d1 LD50 (rat, oral) 1707 mg/kg
Mouse (78-week feed) 731850 mg kg1 d1 LD50 (mouse, oral) 1190 mg/kg
Dog (1-year feed) 100 mg kg1 d1 LD50 (rabbit, oral) 2000 mg/kg
Rat 2-generation feed) 1618 mg kg1 d1 LD50 (rabbit, dermal) > 2000 mg/kg
(parental) LC50 (rat, 4-h inhalation) > 9.6 mg/L air
Rat 2-generation feed) 781 mg kg1 d1 Rabbit: moderately
(developmental) irritating to skin
ADI 0.25 mg kg1 d1 Rabbit: severely irritating
RfD 0.015 mg kg1 d1 to eyes (corrosive)
Guinea pig: a potential
skin sensitizer
Nonmutagenic
Ecological [13, 5]: NOEL/NOAEL:
Rat (2-generation feed) 40 mg kg1 d1
LD50 (mallard duck, oral) 4640 mg/kg (parental)
LC50 (rainbow trout, 96-h) 10 mg/L Rat (2-generation feed) 400 mg kg1 d1
EC50 (daphnia magna, 48-h) 1000 mg/L (developmental)
LD50 (honeybee) 14.5 mg/bee Rat (teratogenicity, gavage) 160 mg kg1 d1
(maternal)
Rat (teratogenicity, gavage) > 400 mg kg1 d1
(developmental)
Chlorthal-dimethyl [1861-32-1] Rabbit (teratogenicity, gavage) 30 mg kg1 d1
Mammalian [13, 5, 568]: (maternal)
Rabbit (teratogenicity, gavage) 300 mg kg1 d1
(developmental)
LD50 (rat, oral) >2000 mg/kg Rat (2-year feed) 110125 mg kg1 d1
LD50 (rabbit, dermal) >2000 mg/kg Dog (1-year feed) 5260 mg kg1 d1
LC50 (rat, 4-h inhalation) >5.2 mg/L air Mouse (18-month feed) 115 mg kg1 d1
Rabbit: nonirritating to skin ADI/ARfD/AOEL 0.3 mg kg1 d1
Rabbit: mild eye irritant RfD 0.03 mg kg1 d1
Guinea pig: not a sensitizer
Nonmutagenic
NOEL/NOAEL:
Rat (2-year feed) 1 mg kg1 d1
Mouse (2-year feed) 435 mg kg1 d1 Ecological [1, 2]:
Dog (2-year feed) 250 mg kg1 d1
Rat (2-generation feed) 63 mg kg1 d1
LD50 (mallard duck, oral) 1373 mg/kg
(parental and
LC50 (rainbow trout, 96-h) 100 mg/L
developmental)
EC50 (daphnia magna, 48-h) 111 mg/L
Rat (teratogenicity, gavage) 2000 mg kg1 d1
EC50 (algae, 72-h) 1.8 mg/L
(maternal and
LD50 (honeybee, oral) 100 mg/bee
developmental)
LC50 (earthworm, 14-d) 1000 mg/kg soil
Rabbit (teratogenicity, gavage) 250 mg kg1 d1
(maternal)
Rabbit (teratogenicity, gavage) 500 mg kg1 d1
(developmental)
ADI/RfD 0.5 mg kg1 d1 Pyriminobac-methyl [136191-64-5]
Mammalian [2, 388]:

Ecological [13, 5]: LD50 (rat, oral) >5000 mg/kg

LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 5.5 mg/L air
LD50 (mallard duck, oral) 2250 mg/kg Rabbit: slightly irritating to skin and eyes
LC50 (rainbow trout, 96-h) 4.7 mg/L Nonmutagenic
360 Weed Control, 2. Individual Herbicides Vol. 39
NOEL/NOAEL: LC50 (rat, 4-h inhalation) 5.2 mg/L air
ADI 0.009 mg kg1 d1 Rabbit: nonirritating
to skin and eyes
Guinea pig: a sensitizer
Ecological [2]: NOEL/NOAEL:
Dog (1-year feed) 140 mg kg1 d1
Mouse (18-month feed) 38 mg kg1 d1
LD50 (mallard duck, oral) 2000 mg/kg Rat (2-year feed) 478 mg kg1 d1
LC50 (rainbow trout, 96-h) 21 mg/L Rat (2-generation, feed) 200 mg kg1 d1
EC50 (daphnia magna, 48-h) 64 mg/L (parental and
EC50 (algae, 72-h) 21 mg/L developmental)
LD50 (honeybee, contact) 200 mg/bee Rat (teratogenicity, gavage) 146 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil (maternal and
developmental)
Rabbit (teratogenicity, gavage) 200 mg kg1 d1
Pyrithiobac-sodium [123343-16-8] (maternal and
Mammalian [13, 569]: developmental)
RfD 0.38 mg kg1 d1

LD50 (rat, oral) 3300 mg/kg

LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 6.9 mg/L air
Rabbit: eye irritant
Ecological [1, 2, 390]:
Rabbit: moderately irritating to skin
Guinea pig: not a sensitizer
Nonmutagenic
NOEL/NOAEL: LD50 (mallard duck, oral) >2000 mg/kg
Dog (1-year feed) 143166 mg kg1 d1 LC50 (rainbow trout, 96-h) 100 mg/L
Rat (2-year feed) 59278 mg kg1 d1 EC50 (daphnia magna, 48-h) 30 mg/L
Mouse (78-week feed) 217319 mg kg1 d1 EC50 (algae, 72-h) 6.5 mg/L
Rat (2-generation feed) 103 mg kg1 d1 LD50 (honeybee, contact) 181 mg/bee
(parental)
Rat (2-generation feed) 508 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) 200 mg kg1 d1
(maternal)
Quinmerac [90717-03-6]
Rat (teratogenicity, gavage) 600 mg kg1 d1 Mammalian [1, 2]:
(developmental)
Rabbit (teratogenicity, gavage) 1000 mg kg1 d1
(maternal) LD50 (rat, oral) 5000 mg/kg
Rabbit (teratogenicity, gavage) 300 mg kg1 d1 LD50 (rat, dermal) >2000 mg/kg
(developmental) LC50 (rat, 4-h inhalation) 5.4 mg/L air
RfD 0.58 mg kg1 d1 Rabbit: not a skin irritant
Rabbit: irritating to eyes
Guinea pig: a sensitizer
Ecological [13]: NOEL/NOAEL:
Rat (2-year feed) 404469 mg kg1 d1
Dog (1-year feed) 8 mg kg1 d1
LD50 (mallard duck, oral) 2250 mg/kg Mouse (78-week feed) 38 mg kg1 d1
LC50 bluegill sunfish, 96-h) 930 mg/L ADI/AOEL 0.079 mg kg1 d1
EC50 (daphnia magna, 48-h) 1100 mg/L ARfD 0.3 mg kg1 d1
EC50 (algae, 72-h) 0.107 mg/L
LD50 (honeybee, contact) 25 mg/bee

Ecological [1, 2]:

2.20. Quinolinecarboxylic Acids
LD50 (mallard duck, oral) 2000 mg/kg
Quinclorac [84087-01-4] LC50 (rainbow trout, 96-h) 87 mg/L
Mammalian [1, 2, 390]: EC50 (daphnia magna, 48-h) 100 mg/L
EC50 (algae, 72-h) 49 mg/L
LD50 (honeybee, contact) 100 mg/bee
LD50 (rat, oral) 2680 mg/kg LC50 (earthworm, 14-d) 1000 mg/kg soil
LD50 (rat, dermal) >2000 mg/kg
Vol. 39 Weed Control, 2. Individual Herbicides 361
EC50 (daphnia magna, 48-h) 848 mg/L
2.21. Benzoylcyclohexanediones EC50 (algae, 72-h) 1.2 mg/L
LD50 (honeybee, oral) 50 mg/bee
Mesotrione [104206-82-8] LC50 (earthworm, 14-d) 1000 mg/kg soil
Mammalian [2, 3, 391, 570]:

LD50 (rat, oral) >5000 mg/kg

LD50 (rat, dermal) >2000 mg/kg Tefuryltrione [473278-76-1]
LC50 (rat, 4-h inhalation) 4.75 mg/L air Mammalian [395, 396]:
Rabbit: irritating to skin and eyes
Nonmutagenic
NOEL/NOAEL: LD50 (rat, oral) >2500 mg/kg
Rat (2-year feed) 0.160.19 mg kg1 d1 LD50 (rat, dermal) >2500 mg/kg
Mouse (78-week feed) 5672 mg kg1 d1 LD50 (mouse, oral) >2000 mg/kg
Rat (2-generation feed) 10 mg kg1 d1 LC50 (rat, 4-h inhalation) 1.34 mg/L air
(parental) Nonmutagenic
Rat (2-generation feed) 1450 mg kg1 d1 NOEL/NOAEL:
(developmental) Rat (2-year feed) 0.08011 mg kg1 d1
Rat (teratogenicity, gavage) 100 mg kg1 d1 Mouse (18-month feed) 27 mg kg1 d1
(maternal and Rat (2-generation feed) 0.126 mg kg1 d1
developmental) (parental)
Mouse (teratogenicity, gavage) 600 mg kg1 d1 Rat (2-generation feed) 0.142 mg kg1 d1
(maternal) (developmental)
Mouse (teratogenicity, gavage) 150 mg kg1 d1 Rat (teratogenicity, gavage) 30 mg kg1 d1
(developmental) (maternal and
RfD 0.0007 mg kg1 d1 developmental)
ADI 0.01 mg kg1 d1 Rabbit (teratogenicity, gavage) 10 mg kg1 d1
AOEL 0.015 mg kg1 d1 (maternal and
developmental)
ADI 0.0008 mg kg1 d1

Ecological [2, 3, 391]:

LD50 (mallard duck, oral) >5000 mg/kg Ecological [395, 396]:

LC50 (rainbow trout, 96-h) >120 mg/L
EC50 (daphnia magna, 48-h) 622 mg/L
LC50 (carp, 96-h) 0.099 mg/L
EC50 (algae, 72-h) 3.5 mg/L
EC50 (daphnia magna, 48-h) >0.099 mg/L
LD50 (honeybee, oral) 11 mg/bee
EC50 (algae, 72-h) 5 mg/L
LC50 (earthworm, 14-d) 438 mg/kg soil

Sulcotrione [99105-77-8] Tembotrione [335104-84-2]

Mammalian [2, 393, 394]: Mammalian [2, 397, 461, 571]:

LD50 (rat, oral) >5000 mg/kg LD50 (rat, oral) >2000 mg/kg
LD50 (rat, dermal) >2000 mg/kg LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 1.63 mg/L air LC50 (rat, 4-h inhalation) >5.03 mg/L air
Rabbit: irritating to eyes Rabbit: nonirritating to skin and eyes
Rabbit: not a skin irritant Guinea pig: a sensitizer
Guinea pig: not a sensitizer Nonmutagenic
NOEL/NOAEL: NOEL/NOAEL:
Rat (2-year feed) 0.5 mg kg1 d1 Rat (2-year feed) 0.040.10 mg kg1 d1
ADI 0.0004 mg kg1 d1 Dog (1-year feed) 10.2 mg kg1 d1
AOEL 0.0006 mg kg1 d1 Rat (2-generation feed) 0.8 mg kg1 d1
(parental and
developmental)
Rat (2-generation feed) 25 mg kg1 d1
Ecological [2]: (maternal)
Rat (teratogenicity, gavage) >25 mg kg1 d1
(developmental)
LD50 (mallard duck, oral) 1350 mg/kg Rat (teratogenicity, gavage) 10 mg kg1 d1
LC50 (rainbow trout, 96-h) 227 mg/L (maternal)
362 Weed Control, 2. Individual Herbicides Vol. 39
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Rabbit (teratogenicity, gavage) 1 mg kg d LC50 (rat, 4-h inhalation) 3.97 mg/L air
(developmental) Rabbit: nonirritating
RfD (US) 0.0004 mg kg1 d1 to skin and eyes
ARfD 0.0008 mg kg1 d1 Nonmutagenic
ADI/ARfD/AOEL (EU) 0.01 mg kg1 d1 NOEL/NOAEL:
Rat (2-year feed) 113143 mg kg1 d1
Dog (2-year feed) 109118 mg kg1 d1
Mouse (80-week feed) 161204 mg kg1 d1
Ecological [2]: Rat (2-generation) 245296 mg kg1 d1
(parental and
LD50 (mallard duck, oral) 292 mg/kg developmental)
LC50 (rainbow trout, 96-h) 100 mg/L Rat (teratogenicity, gavage) 100 mg kg1 d1
NOEC (daphnia magna, 21-d) 5 mg/L (maternal)
EC50 (algae, 72-h) 0.38 mg/L Rat (teratogenicity, gavage) 1000 mg kg1 d1
LD50 (honeybee, oral) 93 mg/bee (developmental)
LC50 (earthworm, 14-d) 1000 mg/kg soil Rabbit: (teratogenicity, gavage) 600 mg kg1 d1
(maternal)
Rabbit: (teratogenicity, gavage) 1200 mg kg1 d1
(developmental)
RfD 1.09 mg kg1 d1
2.22. Benzofurans ARfD 6.0 mg kg1 d1
ADI 0.07 mg kg1 d1
Benfuresate [68505-69-1] AOEL 2.5 mg kg1 d1
Mammalian [1, 2, 399, 503]:

LD50 (rat, oral) 20313536 mg/kg Ecological [13, 400, 401]:

LD50 (mouse, oral) 19802809 mg/kg
LD50 (rat, dermal) >5000 mg/kg
LD50 (mallard duck, oral) 2000 mg/kg
LC50 (rat, 4-h inhalation) >5.34 mg/L air
LC50 (carp, 96-h) 11 mg/L
Rabbit: nonirritating
EC50 (daphnia magna, 48-h) 14 mg/L
to skin and eyes
EC50 (algae, 72-h) 3.9 mg/L
Guinea pig: not a sensitizer
LD50 (honeybee, oral) 50 mg/bee
Nonmutagenic
LC50 (earthworm, 14-d) 134 mg/kg soil
NOEL/NOAEL:
Mouse (18-month feed) 55 mg kg1 d1
Rat (2-year feed) 3.07 mg kg1 d1
Dog (1-year gavage) 40 mg kg1 d1
Rat (2-generation feed) 4.9 mg kg1 d1 2.23. Dicarboximides
(parental)
Rat (2-generation feed) 50 mg kg1 d1 Cinidon-ethyl [142891-20-1]
(developmental)
Rat (teratogenicity, gavage) 3 mg kg1 d1 Mammalian [2, 402, 461, 494]:
(maternal)
Rat (teratogenicity, gavage) 1000 mg kg1 d1 LD50 (rat, oral) >2200 mg/kg
(developmental) LD50 (rat, dermal) >2000 mg/kg
ADI 0.0260.0307 mg kg1 d1 LC50 (rat, 4-h inhalation) >5.3 mg/L air
Rabbit: nonirritating
to skin and eyes
Guinea pig: a sensitizer
Ecological [2]: NOEL/NOAEL:
Rat (2-year feed) 5 mg kg1 d1
LD50 (mallard duck, oral) 10 000 mg/kg Dog (1-year feed) 1 mg kg1 d1
LC50 (rainbow trout, 96-h) 12.3 mg/L Rat (2-generation feed) 51 mg kg1 d1
EC50 (daphnia magna, 48-h) 35 mg/L (parental)
EC50 (algae, 72-h) 3.8 mg/L Rat (teratogenicity, gavage) 1000 mg kg1 d1
LC50 (earthworm, 14-d) 734 mg/kg soil ADI 0.01 mg kg1 d1
AOEL 0.02 mg kg1 d1

Ethofumesate [26225-79-6]
Mammalian [13, 400, 401]: Ecological [2]:

LD50 (rat, oral) 1130 5000 mg/kg LD50 (bobwhite quail, oral) >2000 mg/kg
LD50 (rat, dermal) >2000 mg/kg LC50 (rainbow trout, 96-h) 39200 mg/L
Vol. 39 Weed Control, 2. Individual Herbicides 363
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EC50 (daphnia magna, 48-h) 59.2 mg/L Rabbit (teratogenicity, gavage) 3000 mg kg d
EC50 (algae, 72-h) 0.021 mg/L (developmental)
LD50 (honeybee, oral) >200 mg/bee RfD (US) 0.002 mg kg1 d1
LC50 (earthworm, 14-d) >1000 mg/kg soil ARfD (US) 0.003 mg kg1 d1
ADI (EU) 0.009 mg kg1 d1
ARfD (EU) 0.05 mg kg1 d1
AOEL (EU) 0.018 mg kg1 d1
Flumiclorac-pentyl [87546-18-7]
Mammalian [1, 2, 572]:
Ecological [13, 404]:
LD50 (rat, oral) >5000 mg/kg
LD50 (rat, dermal >2000 mg/kg
LD50 (bobwhite quail, oral) 2250 mg/kg
LC50 (rat, 4-h inhalation) 5.51 mg/L air
LC50 (rainbow trout, 96-h) 2.3 mg/L
Rabbit: skin and eye irritant
RC50 (daphnia magna, 48-h) 5.9 mg/L
Guinea pig: a sensitizer
EC50 (algae, 72-h) 0.000852 mg/L
Nonmutagenic
LD50 (honeybee, oral) 100 mg/bee
NOEL/NOAEL:
LC50 (earthworm, 14-d) 982 mg/kg soil
Rat (2-year feed) 35.443.6 mg kg1 d1
Dog (1-year feed) 100 mg kg1 d1
Mouse (78-week feed) 31.545 mg kg1 d1
Rat (2-generation feed) 1553 mg kg1 d1
(parental) 2.24. Dinitrophenol Herbicides
Rat (2-generation feed) 1716 mg kg1 d1
(developmental)
RfD 0.35 mg kg1 d1
Dinoseb [88-85-7]
Mammalian [2, 3, 5, 407, 466]:

LD50 (rat, oral) 2559 mg/kg

Ecological [1, 2, 573]: LD50 (rabbit, dermal) 80200 mg/kg
LD50 (guinea pig, oral) 25 mg/kg
Rabbit: mild skin irritant
LC50 (rainbow trout, 96-h) 1.1 mg/L Rabbit: mild to moderate eye irritant
EC50 (daphnia magna, 48-h) 38 mg/L NOEL/NOAEL:
LD50 (honeybee, contact) 196 mg/bee Dog (90-d feed) 0.1 mg kg1 d1
Rat (180-d feed) 5 mg kg1 d1
Mouse (2-year feed) <1 mg kg1 d1
Rat (3-generation feed) 1 mg kg1 d1
Rat (teratogenicity, gavage) 3 mg kg1 d1
Flumioxazin [103361-09-7] (maternal and
Mammalian [13, 404, 405]: developmental)
ADI 0.0011 mg kg1 d1
LD50 (bobwhite quail, oral) 2250 mg/kg
LD50 (rat, oral) >5000 mg/kg
LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 3.93 mg/L air Ecological [2, 3, 5]:
Rabbit: mild eye irritant
Rabbit: not a skin irritant
LD50 (mallard duck, oral) 9.5 mg/kg
Guinea pig: not a sensitizer
LC50 (rainbow trout, 96-h) 0.044 mg/L
Nonmutagenic
EC50 (daphnia magna, 48-h) 0.24 mg/L
NOEL/NOAEL:
Rat (2-year feed) 1.82.2 mg kg1 d1
Mouse (78-week feed) 754859 mg kg1 d1
Dog (1-year capsules) 100 mg kg1 d1
Rat (2-generation feed) 12.715.1 mg kg1 d1 Dinoterb [1420-07-1]
(parental) Mammalian [13]:
Rat (2-generation feed) 18.9 mg kg1 d1
(developmental)
Rat (teratogenicity, dermal) 300 mg kg1 d1 LD50 (rat, oral) 62 mg/kg
(maternal) LD50 (mouse, oral) 25 mg/kg
Rat (teratogenicity, dermal) 30 mg kg1 d1 LD50 (rabbit, oral) 28 mg/kg
(developmental) LD50 (guinea pig, dermal) 150 mg/kg
Rabbit (teratogenicity, gavage) 1100 mg kg1 d1 NOEL/NOAEL:
(maternal) Rat (2-year feed) 0.375 mg kg1 d1
364 Weed Control, 2. Individual Herbicides Vol. 39
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Rat (teratogenicity, gavage) 1.25 mg kg d
(maternal)
Ecological [13, 5]:
Rat (teratogenicity, gavage) 1.5 mg kg1 d1
(developmental) LD50 (bird, oral) 5660 mg/kg
LC50 (rainbow trout, 96-h) 100 mg/L
EC50 (daphnia magna, 48-h) 6 mg/L
EC50 (algae, 72-h) 20 mg/L
Ecological [13]: LC50 (earthworm, 14-d) 1058 mg/kg soil

LC50 (rainbow trout, 96-h) 0.0034 mg/L

EC50 (daphnia magna, 48-h) 0.47 mg/L
EC50 (algae, 72-h) 7.4 mg/L
Flupropanate-sodium [22898-01-7]
Mammalian [1, 2, 471]:
DNOC [534-52-1]
LD50 (rat, oral) >8000-11 900 mg/kg
Mammalian [13]: LD50 (mouse, oral) 9600 mg/kg
LD50 (rat, dermal) > 5500 mg/kg
LD50 (rat, oral) 16100 mg/kg LD50 (rabbit, dermal) > 4000 mg/kg
LD50 (rat, dermal) 187>2000 mg/kg LC50 (rat, 14-day inhalation) > 1.74 mg/L air
LD50 (cat, oral) 50 mg/kg Rabbit: mild skin and eye irritant
LC50 (rat, 4-h inhalation) 40230 mg/L air NOEL/NOAEL:
Rabbit: skin and eye irritant Rat (teratogenicity, gavage) 5 mg kg1 d1
Guinea pig: a sensitizer Rat (90-day feed) 0.26 mg kg1 d1
NOEL/NOAEL: Rat (2-generation feed) 5 mg kg1 d1
Rat (2-year feed) 0.594.12 mg kg1 d1 Mouse (1-year feed) 0.9 mg kg1 d1
Rabbit (teratogenicity, gavage) 10 mg kg1 d1 ADI 0.002 mg kg1 d1
Rat (2-generation feed) 1.732.24 mg kg1 d1
No ADI assigned

Ecological [1, 2]:

Ecological [13]: LD50 (Japanese quail, oral) 6750 mg/kg
LC50 (rainbow trout, 96-h) 10 000 mg/L
LD50 (mallard duck, oral) 22.7 mg/kg
LC50 (rainbow trout, 96-h) 66 mg/L
EC50 (daphnia duplex, 48-h) 145 mg/L
EC50 (algae, 96-h) 6 mg/L
LD50 (honeybee) 1.82.3 mg/bee
Iodomethane [74-88-4]
LC50 (earthworm, 14-d) 15 mg/kg soil Mammalian [2, 3, 410, 573]:

LD50 (rat, oral) 80132 mg/kg

LD50 (rat, dermal) >2000 mg/kg
2.25. Aliphatic Compounds LC50 (rat, 4-h inhalation) >4 mg/L air
Rabbit: skin and eye irritant
Dalapon-sodium [127-20-8] Guinea pig: not a sensitizer
Mammalian [13, 5, 466]: Nonmutagenic
NOEL/NOAEL:
Rat (2-year feed) 0.25 mg kg1 d1
LD50 (rat, oral) 75709330 mg/kg Rat (2-generation inhalation) 0.11 mg kg1 d1
LD50 (mouse, oral) > 4600 mg/kg (parental)
LD50 (rabbit, oral) 3860 mg/kg Rat (2-generation inhalation) 0.03 mg kg1 d1
LD50 (rabbit, dermal) > 2000 mg/kg (developmental)
LC50 (rat, 8-h inhalation) > 20 mg/L air Dog (1-year capsules) <1.5 mg kg1 d1
Rabbit: moderately irritating Mouse (78-week feed, 810 mg kg1 d1
to skin and eyes microencapsulated)
Guinea pig: a moderate sensitizer Rabbit (teratogenicity, inhalation) 0.057 mg kg1 d1
NOEL/NOAEL: (maternal)
Dog (1-year feed) 50 mg kg1 d1 Rabbit (teratogenicity, inhalation) 0.011 mg kg1 d1
Rat (2-year feed) 15 mg kg1 d1 (developmental)
RfD 0.03 mg kg1 d1 ADI: not allocated
Vol. 39 Weed Control, 2. Individual Herbicides 365
LC50 (rat, 4-h inhalation) 3.95.59 mg/L air
Methyl Bromide [74-89-9] Rabbit: mild eye irritant
Mammalian [1, 3, 5, 411]: Rabbit: minimally irritating to skin
Guinea pig: not a sensitizer
LD50 (rat, oral) 86214 mg/kg NOEL/NOAEL:
LC50 (rat, 4- inhalation) 780 ppm Rat (2-year feed) 5 mg kg1 d1
Rabbit: strong skin and eye irritant Rat (2-generation feed) 1070 mg kg1 d1
Possibly mutagenic (parental)
NOEL/NOAEL: Rat (2-generation feed) 500 mg kg1 d1
Rat (2-year capsules) <0.025 mg kg1 d1 (developmental)
Dog (1-year feed) 0.0375 mg kg1 d1 Rabbit (teratogenicity, gavage) 475 mg kg1 d1
Mouse (2-year inhalation) <1.5 mg kg1 d1 (maternal and
Rat (2-generation inhalation) 0.15 mg kg1 d1 developmental)
(parental and RfD 0.03 mg kg1 d1
developmental)
RfD 0.0014 mg kg1 d1
ADI 0.11 mg kg1 d1
Ecological [13, 5, 413]:

Ecological [1, 3, 5, 411]: LD50 (bobwhite quail, oral) >2510 mg/kg

LC50 (rainbow trout, 96-h) <100 mg/L
LD50 (bird, oral) 73 mg/kg EC50 (daphnia magna, 48-h) 920 mg/L
LC50 (fish, 96-h) 3.9 mg/L EC50 (algae, 72-h) 133 mg/L
EC50 (daphnia magna, 48-h) 2.6 mg/L LD50 (honeybee, oral) 75 mg/bee
EC50 (algae, 72-h) 2.2 ppm LC50 (earthworm, 14-d) 750 mg/kg soil

2.26. Inorganic Compounds 2.27. Oxadiazolones

Ammonium Sulfamate [7773-06-0] Methazole [20354-26-1]

Mammalian [13, 5, 412]: Mammalian [2, 3, 466, 570]:

LD50 (rat, oral) 16003900 mg/kg LD50 (rat, oral) 777 mg/kg
LD50 (mouse, oral) 1438 mg/kg LD50 (rabbit, dermal) 12 500 mg/kg
LD50 (sheep, oral) >28 000 mg/kg LC50 (rat, 4-h inhalation) 200 mg/L air
Rabbit: a skin and eye irritant NOEL/NOAEL:
Guinea pig: a sensitizer Rabbit (teratogenicity, gavage) 10 mg kg1 d1
NOEL/NOAEL ADI 0.0004 mg kg1 d1
Rat (3.5-month feed) 50 mg kg1 d1
Rat (105-day feed) 500 mg kg1 d1
Rat (3-generation feed) 25 mg kg1 d1
RfD 0.025 mg kg1 d1
Ecological [2, 3]:

Ecological [13, 5, 412, 480]: LD50 (bobwhite quail, oral) 2838 mg/kg
LC50 (rainbow trout, 96-h) 2.5 mg/L
LD50 (mallard duck, oral) 4200 mg/kg EC50 (daphnia magna, 48-h) 1.3 mg/L
LC50 (rainbow trout) 650 mg/L EC50 (algae, 72-h) 0.3 mg/L
LD50 (honeybee) 362 mg/bee

Copper Sulfate [12527-76-3] (see ! Fungi-

cides, Agricultural) ! Fungicides, Agricultural,
3. Toxicology Oxadiargyl [39807-15-3]
Mammalian [2, 414]:
Sodium Chlorate [7775-09-9]
Mammalian [13, 5, 413]: LD50 (rat, oral) 802 mg/kg
LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 5.16 mg/L air
LD50 (rat, oral) >5000 mg/kg Rabbit: nonirritating to skin and eyes
LD50 (rat, dermal) >2000 mg/kg Guinea pig: not a sensitizer
366 Weed Control, 2. Individual Herbicides Vol. 39
NOEL/NOAEL: Guinea pig: not a sensitizer
Rat (2-year feed) 0.8 mg kg1 d1 NOEL/NOAEL:
Dog (1-year feed) 1 mg kg1 d1 Rat (2-year feed) 56.2 mg kg1 d1
Rat (2-generation feed) 4.0 mg kg1 d1 RfD 0.05 mg kg1 d1
Rabbit (teratogenicity, gavage) 10 mg kg1 d1
(maternal)
ADI 0.008 mg kg1 d1
AOEL 0.006 mg kg1 d1 Ecological [13, 416]:

LD50 (mallard duck, oral) >2000 mg/kg

LC50 (rainbow trout, 96-h) 0.87 mg/L
Ecological [2, 414, 480]: EC50 (daphnia magna, 48-h) 1.3 mg/L
EC50 (algae, 72-h) 1.4 mg/L
LD50 (honeybee, oral) 100 mg/bee
LD50 (bobwhite quail, oral) >2000 mg/kg LC50 (earthworm, 14-d) 500 mg/kg soil
LC50 (rainbow trout, 96-h) 0.2 mg/L
EC50 (daphnia magna, 48-h) 530 mg/L
EC50 (algae, 72-h) 0.001 mg/L
LD50 (honeybee, oral) 200 mg/bee Isoxaflutole [141112-29-0]
LC50 (earthworm, 14-d) 1000 mg/kg soil
Mammalian [13, 418, 419, 575]:

LD50 (rat, oral) > 5000 mg/kg

Oxadiazon [19666-30-9] LD50 (rabbit, dermal) > 2000 mg/kg
LC50 (rat, 4-h inhalation) > 5.23 mg/L air
Mammalian [13, 446, 574]: Rabbit: nonirritating to skin
Rabbit: minimally irritating to eyes
LD50 (rat, oral) >5000 mg/kg Guinea pig: not a skin sensitizer
LD50 (rat, dermal) >2000 mg/kg Nonmutagenic
LC50 (rat, 4-h inhalation) 1.94 mg/L air NOEL/NOAEL:
Rabbit: mild eye irritant Rat (neurotoxicity, acute gavage) 125 mg/kg
Rabbit: nonirritating to skin Rat (2-generation feed) 1.76 mg kg1 d1
Guinea pig: not a sensitizer (parental)
NOEL/NOAEL: Rat (2-generation feed) > 437 mg kg1 d1
Rat (2-year feed) 0.5 mg kg1 d1 (developmental)
Dog (2-year feed) 2.5 mg kg1 d1 Rat (teratogenicity, gavage) 100 mg kg1 d1
ADI 0.0036 mg kg1 d1 (maternal)
AOEL 0.18 mg kg1 d1 Rat (teratogenicity, gavage) 10 mg kg1 d1
(developmental)
Rabbit (teratogenicity, gavage) 20 mg kg1 d1
(maternal)
Rabbit (teratogenicity, gavage) <5 mg kg1 d1
Ecological [13]: (developmental)
Rat (2-year feed) 2.0 mg kg1 d1
Dog (1-year feed) 44.8 mg kg1 d1
LD50 (bobwhite quail, oral) 2150 mg/kg
Mouse (18-month feed) 3.2 mg kg1 d1
LC50 (rainbow trout, 96-h) 1.2 mg/L
RfD 0.002 mg kg1 d1
EC50 (daphnia magna, 48-h) 2.4 mg/L
EC50 (algae, 72-h) 0.004 mg/L
LD50 (honeybee, contact) 25 mg/bee
LC50 (earthworm, 14-d) 55 mg/kg soil
Ecological [13, 418, 419]:

LD50 (mallard duck, oral) 2150 mg/kg

2.28. Oxazoles LC50 (rainbow trout, 96-h) 1.7 mg/L
EC50 (daphnia magna, 48-h) 1.5 mg/L
EC50 (algae, 72-h) 0.12 mg/L
Isoxaben [82558-50-7] LD50 (honeybee, contact) 100 mg/bee
Mammalian [13, 416, 466]: LC50 (earthworm, 14-d) 1000 mg/kg soil

LD50 (rat, oral) >10 000 mg/kg

LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 1.99 mg/L air Pyroxasulfone [447399-55-5] Currently no
Rabbit: skin and eye irritant toxicological data are available.
Vol. 39 Weed Control, 2. Individual Herbicides 367

Topramezone [210631-68-8] Fluazolate [174514-07-9]

Mammalian [2, 3, 222]: Mammalian [2]:

LD50 (rat, oral) >2000 mg/kg LD50 (rat, oral) 5000 mg/kg
LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) >5.05 mg/L air
Rabbit: irritating to skin and eyes
Guinea pig: not a sensitizer Ecological [2]:
Nonmutagenic
NOEL/NOAEL:
LD50 (mallard duck, oral) 2130 mg/kg
Rat (2-generation feed) 0.4-0.5 mg kg1 d1
LC50 (rainbow trout, 96-h) 0.045 mg/L
(parental and
EC50 (daphnia magna, 48-h) 0.039 mg/L
developmental)
LC50 (earthworm, 14-d) 1170 mg/kg soil
Rat (2-year feed) 0.4.0.5 mg kg1 d1
Dog (2-year feed) 2.915.4 mg kg1 d1
Mouse (78-week feed) <19 mg kg1 d1
Rat (teratogenicity, gavage) <100 mg kg1 d1 Pinoxaden [243973-20-8]
(maternal and
developmental)
Mammalian [2, 424]:
Rabbit (teratogenicity, gavage) 0.5 mg kg1 d1
(maternal and LD50 (rat, oral) >5000 mg/kg
developmental) LD50 (rat, dermal) >2000 mg/kg
RfD 0.004 mg kg1 d1 LC50 (rat, 4-h inhalation) >5.22 mg/L air
ARfD 0.005 mg kg1 d1 Rabbit: nonirritating to skin and eyes
Guinea pig: not a sensitizer
Nonmutagenic
NOEL/NOAEL:
Ecological [2, 3]: Rat (2-year gavage) 100 mg kg1 d1
Mouse (78-week feed) 181216 mg kg1 d1
LD50 (bobwhite quail, oral) >2000 mg/kg Dog (2-year capsules) 125 mg kg1 d1
LC50 (rainbow trout, 96-h) 100 mg/L Rat (2-generation feed) 250 mg kg1 d1
EC50 (daphnia magna, 48-h) 100 mg/L (parental and
EC50 (algae, 72-h) 17.2 mg/L developmental)
LD50 (honeybee, oral) 72 mg/bee Rat (teratogenicity, gavage) 30 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil (maternal and
developmental)
Rabbit (teratogenicity, gavage) 30 mg kg1 d1
(maternal,
2.29. Pyrazoles developmental)
ADI/ARfD/AOEL 0.1 mg kg1 d1
RfD/ARfD 0.3 mg kg1 d1
Benzofenap [82692-44-2]
Mammalian [1, 2, 576, 577]:
Ecological [2, 424]:
LD50 (rat, oral) >15 000 mg/kg
LD50 (rat, dermal) >5000 mg/kg
LC50 (rat, 4-h inhalation) >1.93 mg/L air LD50 (mallard duck, oral) 2250 mg/kg
Rabbit: mild skin and eye irritant LC50 (rainbow trout, 96-h) 10.3 mg/L
Guinea pig: weakly sensitizing EC50 (algae, 72-h) 0.91 mg/L
Nonmutagenic LD50 (honeybee, contact) 100 mg/bee
NOEL/NOAEL: LC50 (earthworm, 14-d) 1000 mg/kg soil
ADI 0.0015 mg kg1 d1

Pyraflufen-ethyl [129630-19-9]
Ecological [1, 2, 480, 576]: Mammalian [2, 3, 426, 495, 578]:

LD50 (Japanese quail, oral) >2000 mg/kg LD50 (rat, oral) >5000 mg/kg
LC50 (rainbow trout, 96-h) 0.762 mg/L LD50 (rat, dermal) >2000 mg/kg
EC50 (daphnia magna, 48-h) 0.383 mg/L LC50 (rat, 4-h inhalation) 5.03 mg/L air
EC50 (algae, 72-h) 0.148 mg/L Rabbit: irritating to skin and eyes
Guinea pig: not a sensitizer
368 Weed Control, 2. Individual Herbicides Vol. 39
Nonmutagenic EC50 (daphnia magna, 48-h) 93 mg/L
NOEL/NOAEL: EC50 (algae, 72-h) 30 mg/L
Rat (2-year feed) 87111 mg kg1 d1 LD50 (honeybee, contact) 75 mg/bee
Mouse (78-week feed) 19.621 mg kg1 d1 LC50 (earthworm, 14-d) 1000 mg/kg soil
Dog (1-year feed) >1000 mg kg1 d1
Rat (2-generation feed) 7191 mg kg1 d1
(parental)
Rat (2-generation feed) 721901 mg kg1 d1 Pyrazolinate [58011-68-0]
(developmental) Mammalian [429, 430]:
Rat (teratogenicity, gavage) 20 mg kg1 d1
(maternal)
LD50 (rat, oral) >9550 mg/kg
Rat (teratogenicity, gavage) 60 mg kg1 d1
LD50 (rat, dermal) >5000 mg/kg
(developmental)
LC50 (rat, 4-h inhalation) 2.5 mg/L air
Rabbit (teratogenicity, gavage) 20 mg kg1 d1
Rabbit: mild skin irritant
(maternal)
Rabbit: not an eye irritant
Rabbit (teratogenicity, gavage) 60 mg kg1 d1
Guinea pig: not a sensitizer
(developmental)
Nonmutagenic
ADI/ARfD/RfD 0.20 mg kg1 d1
NOEL/NOAEL:
AOEL 0.112 mg kg1 d1
Rat (teratogenicity, gavage) 1000 mg kg1 d1
(maternal and
developmental)
Ecological [2, 3, 426]: Rabbit (teratogenicity, gavage) 100 mg kg1 d1
(maternal and
LD50 (bobwhite quail, oral) >2000 mg/kg developmental)
LC50 (rainbow trout, 96-h) 0.1 mg/L Rat (2-generation feed) 57.376.0 mg kg1 d1
EC50 (daphnia magna, 48-h) 0.1 mg/L (parental and
EC50 (algae, 72-h) 0.00023 mg/L developmental)
LD50 (honeybee, oral) 100 mg/bee Dog (1-year feed) 51.457.6 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil Rat (2-year feed) 48.5.60.0 mg kg1 d1
Mouse (78-week feed) 350.8463.4 mg kg1 d1
RfD 0.51 mg kg1 d1

Pyrasulfotole [365400-11-9]
Mammalian [2, 3, 427, 579]:
Ecological [429]:
LD50 (rat, oral) >2000 mg/kg
LD50 (rat, dermal) >2000 mg/kg LC50 (carp, 96-h) 92 mg/L
LC50 (rat, 4-h inhalation) >5.03 mg/L air EC50 (daphnia magna, 48-h) 0.53 mg/L
Rabbit: nonirritating to skin
Rabbit: mild eye irritant
Guinea pig: not a sensitizer Pyrazoxyfen [71561-11-0]
Nonmutagenic
NOEL/NOAEL:
Mammalian [1, 2, 580]:
Mouse (78-week feed) 13.616.7 mg kg1 d1
Rat (2-year feed) 1.01.4 mg kg1 d1 LD50 (rat, oral) 16441690 mg/kg
Dog (2-year feed) 37 mg kg1 d1 LD50 (mouse, oral) >8450 mg/kg
Rat (2-generation feed) 2.5-3.1 mg kg1 d1 LD50 (rat, dermal) >5000 mg/kg
(parental and LC50 (rat, 4-h inhalation) 0.28 mg/L air
developmental) Rabbit: slightly irritating to eyes
Rat (teratogenicity, gavage) 10 mg/kg (maternal Rabbit: not a skin irritant
and developmental) Guinea pig: not a sensitizer
Rabbit (teratogenicity, gavage) 75 mg kg1 d1 Nonmutagenic
(maternal) NOEL/NOAEL:
Rabbit (teratogenicity, gavage) 10 mg kg1 d1 Mouse (2-year feed) 0.340.36 mg kg1 d1
(developmental) Rat (2-year feed) 0.1651.30 mg kg1 d1
ADI/RfD 0.01 mg kg1 d1 ADI 0.0015 mg kg1 d1
ARfD 0.020.038 mg kg1 d1

Ecological [1, 2, 480]:

Ecological [2, 3, 427]:
LC50 (rainbow trout, 96-h) 0.79 mg/L
LD50 (bobwhite quail, oral) >2000 mg/kg EC50 (daphnia magna, 48-h) 127 mg/L
LC50 (bluegill sunfish, 96-h) 94 mg/L
Vol. 39 Weed Control, 2. Individual Herbicides 369

2.30. Pyridazines Ecological [13, 435, 480]:

Pyridate [55512-33-9]
LD50 (bobwhite quail, oral) >2000 mg/kg
Mammalian [1, 2, 433]: LC50 (rainbow trout, 96-h) 41.3 mg/L
EC50 (daphnia magna, 48-h) 132 mg/L
LD50 (rat, oral) 40005993 mg/kg EC50 (algae, 72-h) 0.6 mg/L
LD50 (mouse, oral) >10 000 mg/kg LD50 (honeybee, contact) 200 mg/bee
LD50 (rabbit, dermal) > 2000 mg/kg LC50 (earthworm, 14-d) 1000 mg/kg soil
LC50 (rat, 4-h inhalation) > 4.37 mg/L air
Rabbit: slight to moderately
irritating to skin
Rabbit: nonirritating to eyes
Guinea pig: a potential skin sensitizer Flufenpyr-ethyl [188489-07-8]
Nonmutagenic Mammalian [2, 580, 581]:
NOEL/NOAEL:
Rat (3-generation feed) 10.8 mg kg1 d1
(parental and LD50 (rat, oral) >5000 mg/kg
developmental) LD50 (rat, dermal) >5000 mg/kg
Rat (teratogenicity, gavage) 165 mg kg1 d1 LC50 (rat, 4-h inhalation) 5.0 mg/L air
(maternal and Rabbit: nonirritating
developmental) to skin and eyes
Rabbit (teratogenicity, gavage) 300 mg kg1 d1 Guinea pig: not a sensitizer
(maternal) Nonmutagenic
600 mg kg1 d1 NOEL/NOAEL:
(developmental) Dog (1-year feed) 1000 mg kg1 d1
Rat (2-year feed) 10.8 mg kg1 d1 Rat (2-year feed) 7791025 mg kg1 d1
Dog (1-year capsule) 20 mg kg1 d1 Mouse (18-month feed) 39.943.7 mg kg1 d1
Mouse (18-month feed) < 47.7 mg kg1 d1, Rat (2-generation feed) 1463 mg kg1 d1
noncarcinogenic (parental and
RfD 0.11 mg kg1 d1 developmental)
ADI/AOEL 0.036 mg kg1 d1 Rat (teratogenicity, gavage) 1000 mg kg1 d1
(maternal and
developmental)
Rabbit (teratogenicity, gavage) 100
Ecological [1, 2, 433, 480]: (maternal)
Rabbit (teratogenicity, gavage) 1000 mg kg1 d1
LD50 (bobwhite quail, oral) 1269 mg/kg (developmental)
LC50 (rainbow trout, 96-h) 1.2 mg/L ADI 0.39 mg kg1 d1
EC50 (daphnia magna, 48-h) 0.83 mg/L RfD 0.45 mg kg1 d1
EC50 (algae, 72-h) 2 mg/L
LD50 (honeybee, contact) 100 mg/bee
LC50 (earthworm, 14-d) 799 mg/kg soil
Ecological [2, 582]:

2.31. Pyridazinones LD50 (bobwhite quail, oral) >2250 mg/kg

LC50 (rainbow trout, 96-h) 3.7 mg/L
EC50 (daphnia magna, 48-h) 3.0 mg/L
Chloridazon [1698-60-8] EC50 (algae, 72-h) 0.012 mg/L
Mammalian [13, 435]: LD50 (honeybee, contact) 25 mg/bee

LD50 (rat, oral) 17302000 mg/kg

LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 5.4 mg/L air Norflurazon [27314-13-2]
Rabbit: skin and eye irritant Mammalian [13, 5, 436, 466]:
Guinea pig: not a sensitizer
Nonmutagenic
NOEL/NOAEL: LD50 (rat, oral) 50009000 mg/kg
Mouse (2-year feed) 4448 mg kg1 d1 LD50 (rat, dermal) >5000 mg/kg
Rat (2-year feed) 5.4116 mg kg1 d1 LC50 (rat, 4-h inhalation) >200 mg/L air
ADI 0.10.16 mg kg1 d1 Rabbit: irritating to skin and eyes
AOEL 0.2 mg kg1 d1 Guinea pig: not a sensitizer
Nonmutagenic
370 Weed Control, 2. Individual Herbicides Vol. 39
NOEL/NOAEL:
Rat (2-year feed) 18.75 mg kg1 d1
Diquat [2764-72-9]
Mouse (2-year feed 12.858.8 mg kg1 d1 Mammalian [13, 5, 583]:
Rat (3-generation feed) 51 mg kg1 d1
(parental and LD50 (rat, oral) 231 mg/kg
developmental) LD50 (rat, dermal) 400 mg/kg
Rat (teratogenicity, gavage) <100 mg kg1 d1 LD50 (cow, oral) 3056 mg/kg
(maternal and Rabbit: skin and eye irritant
developmental) Guinea pig: a sensitizer
Rabbit (teratogenicity, gavage) 30 mg kg1 d1 NOEL/NOAEL:
(maternal and Rat (2-year feed) 0.580.72 mg kg1 d1
developmental) Dog (1-year feed) 0.5 mg kg1 d1
ADI/RfD 0.02 mg kg1 d1 Mouse (2-year feed) 3.56 mg kg1 d1
Rat (2-generation feed) 0.8 mg kg1 d1
(paternal)
Rat (2-generation feed) 4 mg kg1 d1
Ecological [13, 5, 436]: (developmental)
Rat (teratogenicity, gavage) 814 mg kg1 d1
(maternal)
LD50 (mallard duck, oral) >2510 mg/kg Rat (teratogenicity, gavage) 3256 mg kg1 d1
LC50 (rainbow trout, 96-h) 8.1 mg/L (developmental)
EC50 (daphnia magna, 48-h) 15 mg/L Rabbit (teratogenicity, gavage) 1 mg kg1 d1
EC50 (algae, 72-h) 0.0176 mg/L (maternal)
LD50 (honeybee) 235 mg/bee Rabbit (teratogenicity, gavage) 3 mg kg1 d1
LC50 (earthworm, 14-d) 1000 mg/kg soil (developmental)
ADI 0.002 mg kg1 d1
RfD 0.005 mg kg1 d1

2.32. Quaternary Ammonium

Compounds Ecological [1, 2, 5]:

Difenzoquat-methylsulfate [43222-48-6] LD50 (mallard duck, oral) 564 mg/kg

Mammalian [1, 2, 437]: LC50 (rainbow trout, 96-h) 20 mg/L
EC50 (daphnia magna, 48-h) 3 mg/L
EC50 (algae, 72-h) 0.005 mg/L
LD50 (rat, oral) 270373 mg/kg
LD50 (rabbit, dermal) 3540 mg/kg
LC50 (rat, 4-h inhalation) 0.36 mg/L air
Rabbit: slight eye irritant Paraquat [4685-14-7]
Rabbit: moderate skin irritant
NOEL/NOAEL: Mammalian [13, 5, 584]:
Rat (2-year feed) 250 mg kg1 d1
Rat (3-generation feed) 125 mg kg1 d1 LD50 (rat, oral) 110-344 mg/kg
(parental) LD50 (rabbit, dermal) >2000 mg/kg
Rat (3-generation feed) 25 mg kg1 d1 LC50 (rat, 4-h inhalation) 0.6 mg/L air
(developmental) Rabbit: skin and eye irritant
Rat (teratogenicity, gavage) 125 mg kg1 d1 Guinea pig: sensitizer
(maternal and Nonmutagenic
developmental) NOEL/NOAEL:
ADI 0.0005 mg kg1 d1 Rat (2-year feed) 1.25 mg kg1 d1
Dog (1-year feed) 0.45 mg kg1 d1
Rat (3-generation feed) 1.25 mg kg1 d1
(parental)
Ecological [1, 2, 437]: Rat (3-generation feed) 7.5 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) 1.5 mg kg1 d1
LD50 (bobwhite quail, oral) 4640 mg/kg (maternal)
LC50 (rainbow trout, 96-h) 694 mg/L Rat (teratogenicity, gavage) 5 mg kg1 d1
EC50 (daphnia magna, 48-h) 2.63 mg/L (developmental)
EC50 (algae, 72-h) 0.54 mg/L ADI/AOEL 0.004 mg kg1 d1
LD50 (honeybee, contact) 36 mg/bee RfD 0.0045 mg kg1 d1
LC50 (earthworm, 14-d) 400 mg/kg soil ARfD 0.005 mg kg1 d1
Vol. 39 Weed Control, 2. Individual Herbicides 371
Dog (13-week feed) 7.5 mg kg d1
1
Ecological [13, 5]: Rat (13-week feed) 3.5 mg kg1 d1
ADI 0.1 mg kg1 d1
LD50 (bobwhite quail, oral) 981 mg/kg ARfD 0.25 mg kg1 d1
LC50 (rainbow trout, 96-h) 19 mg/L AOEL 0.13 mg kg1 d1
EC50 (daphnia magna, 48-h) 4.4 mg/L
EC50 (algae, 72-h) 0.23 mg/L
LD50 (honeybee, oral) 9.06 mg/bee
LC50 (earthworm, 14-d) 1000 mg/kg soil
Ecological [1, 2, 5]:

LD50 (bobwhite quail, oral) 1140 mg/kg

LC50 (rainbow trout, 96-h) 100 mg/L
2.33. Miscellaneous Compounds EC50 (daphnia magna, 96-h) 64 mg/L
EC50 (algae, 72-h) 10 mg/L
Acrolein [107-02-8] LD50 (honeybee, oral) 200 mg/bee
Mammalian [13, 438441, 471]: LC50 (earthworm, 14-d) 870 mg/kg soil

LD50 (rat, oral) 2946 mg/kg

LD50 (rat, dermal) 50231 mg/kg
LC50 (rat, 4-h inhalation) 0.019 mg/L air Benzobicyclon [156963-66-5]
Rabbit: skin and eye irritant Mammalian [2, 503]:
Guinea pig: sensitizer
Nonmutagenic
NOEL/NOAEL: LD50 (rat, oral) >5000 mg/kg
Rat (2-generation feed) 3 mg kg1 d1 LD50 (mouse, oral) >5000 mg/kg
(parental and LD50 (rat, dermal) >2000 mg/kg
developmental) LC50 (rat, 4-h inhalation) 2.72 mg/L air
Rat (teratogenicity, gavage) 6 mg kg1 d1 Rabbit: slightly irritating
(maternal and to skin and eyes
developmental) Guinea pig: not a sensitizer
Rabbit (teratogenicity, gavage) 2 mg kg1 d1 Nonmutagenic
(maternal and NOEL/NOAEL:
developmental) Dog (1-year feed) 1000 mg kg1 d1
Rat (2-year feed) 0.75 mg kg1 d1 Rat (2-year feed) 3.43 mg kg1 d1
Dog (1-year capsules) 2 mg kg1 d1 Mouse (18-month feed) 473 mg kg1 d1
ADI 0.0005 mg kg1 d1 Rat (2-generation feed) 72.1 mg kg1 d1
(parental)
Rat (2-generation feed) 77.5 mg kg1 d1
(developmental)
Ecological [13, 438, 441]: Rat (teratogenicity, gavage) 1000 mg kg1 d1
(maternal and
developmental)
LD50 (mallard duck, oral) 9.1 mg/kg ADI 0.034 mg kg1 d1
LC50 (rainbow trout, 96-h) 0.0140.25 mg/L
EC50 (daphnia magna, 48-h) 0.0220.093 mg/L
EC50 (algae, 72-h) 0.0260.05 mg/L

Ecological [2]:

Aminocyclopyrachlor [858956-08-8] No LD50 (mallard duck, oral) 2250 mg/kg

data available yet. LC50 (carp, 96-h) 10 mg/L
EC50 (daphnia magna, 48-h) 1 mg/L
EC50 (algae, 72-h) 1 mg/L
Bentazone [25057-89-0] LD50 (honeybee, oral) 200 mg/bee
Mammalian [1, 2, 5]:

LD50 (rat, oral) 5002063 mg/kg

LD50 (rat, dermal) >5000 mg/kg Chlorflurenol-methyl [2536-31-4]
LC50 (rat, 4-h inhalation) 5.1 mg/L air Mammalian [1, 2, 444]:
Rabbit: severe eye irritant
Rabbit: nonirritating to skin
NOEL/NOAEL: LD50 (rat, oral) 12 800 mg/kg
Mouse (18-month feed) 17.5 mg kg1 d1 LD50 (rat, dermal) 10 000 mg/kg
372 Weed Control, 2. Individual Herbicides Vol. 39
LC50 (rat, 4-h inhalation) 101.5 mg/L air ADI/RfD 0.043 mg kg1 d1
NOEL/NOAEL: ARfD 1.0 mg kg1 d1
Rat (2-year feed) 150 mg kg1 d1 AOEL 0.133 mg kg1 d1
Dog (2-year feed) 7.5 mg kg1 d1
ADI 0.15 mg kg1 d1

Ecological [1, 2, 585]:

Ecological [1, 2, 444]:
LD50 (bobwhite quail, oral) >2510 mg/kg
LD50 (pheasant, oral) 10 000 mg/kg LC50 (rainbow trout, 96-h) 15.519 mg/L
LC50 (rainbow trout, 96-h) 1.16 mg/L EC50 (daphnia magna, 48-h) 5.212.7 mg/L
EC50 (daphnia magna, 48-h) 5.1 mg/L EC50 (algae, 72-h) 0.136 mg/L
LC50 (earthworm, 14-d) 1350 mg/kg soil LD50 (honeybee, oral) 85.3 mg/bee
LC50 (earthworm, 14-d) 78156 mg/kg soil

Cinmethylin (Cycloheptan-ethyl) [87818-

31-3] Endothal [145-73-3]
Mammalian [1, 2, 422, 471]: Mammalian [13, 447, 466]:

LD50 (rat, oral) 4553 mg/kg LD50 (rat, oral) 3851 mg/kg
LD50 (rat, dermal) >2000 mg/kg LD50 (rabbit, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 3.5 mg/L air LC50 (rat, 4-h inhalation) 0.68 mg/L air
Rabbit: skin and eye irritant Rabbit: moderate skin irritant
NOEL/NOAEL: Rabbit: severe eye irritant
Rat (2-year feed) 300 mg kg1 d1 Nonmutagenic
Mouse (18-month feed) 300 mg kg1 d1 NOEL/NOAEL:
Rat (teratogenicity, gavage) 30 mg kg1 d1 Rat (2-year feed) 125 mg kg1 d1
ADI 0.01 mg kg1 d1 Dog (2-year feed) >300 mg kg1 d1
ARfD 0.3 mg kg1 d1 Rat (3-generation feed) 5 mg kg1 d1
(parental and
developmental)
ADI/RfD/ARfD 0.02 mg kg1 d1
Ecological [1, 2]:

LD50 (Japanese quail, oral) >2150 mg/kg

LC50 (rainbow trout, 96-h) 6.6 mg/L Ecological [13]:
EC50 (daphnia magna, 48-h) 7.2 mg/L

LD50 (mallard duck, oral) 5000 mg/kg

LC50 (rainbow trout, 96-h) 78 mg/L
EC50 (daphnia magna) 32.5 mg/L
Clomazone [81777-89-1] EC50 (algae, 72-h) 50 mg/L
Mammalian [1, 5, 293, 445]: Nontoxic to bees

LD50 (rat, oral) 13692077 mg/kg

LD50 (rabbit, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 4.85 mg/L air Fluridone [59756-60-4]
Rabbit: minimally irritating to skin Mammalian [13, 448, 449, 466]:
Rabbit: slight eye irritant
Guinea pig: not a sensitizer
Nonmutagenic LD50 (rat, oral) >10 000 mg/kg
NOEL/NOAEL: LD50 (rabbit, dermal) >5000 mg/kg
Rat (2-year feed) 4.35.5 mg kg1 d1 LC50 (rat, 4-h inhalation) 4.12 mg/L air
Dog (1-year feed) 1414.9 mg kg1 d1 Rabbit: skin and eye irritant
Mouse (2-year feed) 15 mg kg1 d1 Guinea pig: not a sensitizer
Rat (2-generation feed) 50 mg kg1 d1 NOEL/NOAEL:
(parental and Rat (teratogenicity, gavage) 100 mg kg1 d1
developmental) (maternal)
Rat (teratogenicity, gavage) 100 mg kg1 d1 Rat (teratogenicity, gavage) 300 mg kg1 d1
(maternal and (developmental)
developmental) Mouse (2-year feed) 15 mg kg1 d1
Vol. 39 Weed Control, 2. Individual Herbicides 373
1 1
Dog (1-year capsules) 75 mg kg d Rabbit (teratogenicity, gavage) 20 mg kg d1
1

Rat (2-year feed) 8 mg kg1 d1 (maternal and

Rabbit (teratogenicity, gavage) 125 mg kg1 d1 developmental)
(maternal and ADI 0.02 mg kg1 d1
developmental) AOEL 0.03 mg kg1 d1
RfD 0.08 mg kg1 d1
ARfD 1.25 mg kg1 d1

Ecological [1, 2, 452, 453]:

Ecological [13, 449]:
LD50 (bobwhite quail, oral) 2530 mg/kg
LC50 (rainbow trout, 96-h) 7 mg/L
LD50 (bobwhite quail, oral) >2000 mg/kg EC50 (daphnia magna, 48-h) 13 mg/L
LC50 (rainbow trout, 96-h) 11.7 mg/L EC50 (algae, 72-h) 0.02 mg/L
EC50 (daphnia magna, 48-h) 6.3 mg/L LD50 (honeybee, oral) >304 mg/bee
EC50 (algae, 72-h) 4.9 mg/L LC50 (earthworm, 14-d) 1800 mg/kg soil
LD50 (honeybee, oral) 63 mg/bee
LC50 (earthworm, 14-d) 103 mg/kg soil

Fluthiacet-methyl [117337-19-6]
Mammalian [2, 3, 454]:
Flurochloridone [61213-25-0]
Mammalian [1, 2]:
LD50 (rat, oral) > 5000 mg/kg
LD50 (rabbit, dermal) > 2000 mg/kg
LD50 (rat, oral) 3650 mg/kg LC50 (rat, 4-h inhalation) > 5.05 mg/L air
LD50 (rat, dermal) >5000 mg/kg Rabbit: nonirritating to skin
LC50 (rat, 4-h inhalation) 4.82 mg/L air Rabbit: slightly irritating to eyes
NOEL/NOAEL: Nonmutagenic
Rat (2-year feed) 5 mg kg1 d1 NOEL/NOAEL:
ADI 0.02 mg kg1 d1 Rat (2-year feed) 2.12.5 mg kg1 d1
ARfD/AOEL 0.025 mg kg1 d1 Mouse (18-month feed) 0.1 mg kg1 d1
Dog (1-year feed) 3.704.16 mg kg1 d1
Rat (2-generation feed) 2.12.6 mg kg1 d1
(parental)
Rat (2-generation feed) 2.72.9 mg kg1 d1
Ecological [1, 2]: (developmental)
Rat (teratogenicity, gavage) 10 mg kg1 d1
LD50 (bobwhite quail, oral) 2150 mg/kg (maternal)
LC50 (rainbow trout, 96-h) 3 mg/L Rat (teratogenicity, gavage) 20 mg kg1 d1
EC50 (daphnia magna, 48-h) 5.1 mg/L (developmental)
EC50 (algae, 72-h) 0.0047 mg/L ADI/ARfD/RfD 0.001 mg kg1 d1
LD50 (honeybee, oral) 100 mg/bee
LC50 (earthworm, 14-d) 227 mg/kg soil

Ecological [2, 3, 454]:

Flurtamone [96525-23-4] LD50 (bobwhite quail, oral) 2250 mg/kg
Mammalian [1, 2, 452, 453]: LC50 (rainbow trout, 96-h) 0.043 mg/L
EC50 (daphnia magna, 48-h) 2.3 mg/L
EC50 (algae, 72-h) 0.00251 mg/L
LD50 (rat, oral) >5000 mg/kg
LD50 (honeybee, contact) 100 mg/bee
LD50 (rat, dermal) >2000 mg/kg
LC50 (earthworm, 14-d) 948 mg/kg soil
LC50 (rat, 4-h inhalation) >2.2 mg/L air
Rabbit: nonirritating to skin and eyes
Guinea pig: not a sensitizer
Nonmutagenic
NOEL/NOAEL: Indanofan [133220-30-1]
Rat (2-year feed) 2.8 mg kg1 d1 Mammalian [1, 2, 456, 586]:
Dog (1-year feed) 2 mg kg1 d1
Rat (2-generation feed) 25 mg kg1 d1
(parental and LD50 (rat, oral) 460> 1000 mg/kg
developmental) LD50 (rat, dermal) 2000 mg/kg
374 Weed Control, 2. Individual Herbicides Vol. 39
LC50 (rat, 4-h inhalation) >1.57 mg/L air LC50 (rat, 4-h inhalation) 5.1 mg/L air
Rabbit: nonirritating to skin Rabbit: nonirritating
Rabbit: mildly irritating to eyes to skin and eyes
Nonmutagenic Nonmutagenic
NOEL/NOAEL: NOEL/NOAEL:
Rat (2-year feed) 0.3560.432 Dog (1-year feed) 23.125.2 mg kg1 d1
Mouse (78-week feed) 1.9519.2 mg kg1 d1 Rat (2-year feed) 35.243.8 mg/kg(d
Dog (1-year feed) 3.704.16 mg kg1 d1 Mouse (18-month feed) 191203 mg kg1 d1
ADI 0.0035 mg kg1 d1 Rat (2-generation feed) 71.2 mg kg1 d1
(parental)
Rat (2-generation feed) 98.6 mg kg1 d1
(developmental)
Rat (teratogenicity, gavage) 1000 mg kg1 d1
Ecological [1, 2, 586]: (maternal and
developmental)
LD50 (bobwhite quail, oral) 2000 mg/kg ADI 0.23 mg kg1 d1
LC50 (carp, 96-h) 5 mg/L
EC50 (daphnia magna, 48-h) 7.9 mg/L
EC50 (algae, 72-h) 0.00152 mg/L
LD50 (honeybee, contact) 100 mg/bee Ecological [2]:

LD50 (bobwhite quail, oral) >2250 mg/kg

LC50 (carp, 96-h) 21.4 mg/L
Oxaziclomefone [153197-14-9] EC50 (daphnia magna, 48-h) 38.8 mg/L
Mammalian [2, 503]: EC50 (algae, 72-h) 0.00131 mg/L
LD50 (honeybee, contact) 98.7 mg/bee
LC50 (earthworm, 14-d) 851 mg/kg soil
LD50 (rat, oral) >5000 mg/kg
LD50 (rat, dermal) >2000 mg/kg
Rabbit: slightly irritating
to skin and eyes Pyribenzoxim [168088-61-7]
Guinea pig: not a sensitizer
Mammalian [2]:
Nonmutagenic
NOEL/NOAEL:
Dog (1-year feed) 50 mg kg1 d1 LD50 (rat, oral) >5000 mg/kg
Rat (2-year feed) 0.911.14 mg kg1 d1 LD50 (rat, dermal) >2000 mg/kg
Mouse (18-month feed) 14.715.8 mg kg1 d1 LC50 (rat, 4-h inhalation) 5.48 mg/L air
Rat (2-generation feed) 2.42.7 mg kg1 d1 Rabbit: nonirritating to skin and eyes
(parental and Guinea pig: not a sensitizer
developmental) NOEL/NOAEL:
Rat (teratogenicity, gavage) 300 mg kg1 d1 ADI 0.05 mg kg1 d1
(maternal)
Rat (teratogenicity, gavage) 1000 mg kg1 d1
(developmental
ADI 0.0091 mg kg1 d1
Ecological [2]:

LC50 (rainbow trout, 96-h) 100 mg/L

Ecological [2]: EC50 (daphnia magna, 48-h) 100 mg/L
EC50 (algae, 72-h) 100 mg/L
LD50 (honeybee) 100 mg/bee
LC50 (carp, 96-h) 5 mg/L
EC50 (daphnia magna, 48-h) >1 mg/L
EC50 (algae, 72-h) 0.014 mg/L

Pyriftalid [135186-78-6]
Mammalian [2, 587]:
Pentoxazone [110956-75-7]
Mammalian [2, 136, 503]: LD50 (rat, oral) >5000 mg/kg
LD50 (rat, dermal) >2000 mg/kg
LC50 (rat, 4-h inhalation) 5.54 mg/L air
LD50 (rat, oral) >5000 mg/kg Rabbit: nonirritating
LD50 (rat, dermal) >2000 mg/kg to skin and eyes
Vol. 39 Weed Control, 2. Individual Herbicides 375
Guinea pig: not a sensitizer
Nonmutagenic
Tridiphane [58138-08-2]
NOEL/NOAEL: Mammalian [2, 466]:
Rat (2-year feed) 4.315.6 mg kg1 d1
Mouse (18-month feed) 2021.5 mg kg1 d1
LD50 (rat, oral) 17401918 mg/kg
Dog (1-year feed) 29.631.2 mg kg1 d1
LD50 (rabbit, dermal) 3536 mg/kg
Rat (2-generation feed) 7.238.35 mg kg1 d1
NOEL/NOAEL:
(parental)
Rat (2-year feed) 3 mg kg1 d1
Rat (2-generation feed) 10.3 mg kg1 d1
Dog (6-month feed) 10 mg kg1 d1
(developmental)
Rat (2-generation feed) 0.33 mg kg1 d1
Rabbit (teratogenicity, gavage) 1000 mg kg1 d1
(parental and
(maternal and
developmental)
developmental)
Rat (teratogenicity, gavage) 250 mg kg1 d1
ADI 0.0056 mg kg1 d1
(maternal)
Rat (teratogenicity, gavage) 75 mg kg1 d1
(developmental)
RfD 0.003 mg kg1 d1
Ecological [2, 587]:

LD50 (bobwhite quail, oral) 1505 mg/kg

Ecological [2]:
LC50 (rainbow trout, 96-h) 81 mg/L
EC50 (daphnia magna, 48-h) 0.00083 mg/L
EC50 (algae, 72-h) 82.1 mg/L LD50 (mallard duck, oral) >2510 mg/kg
LD50 (honeybee, contact) 100 mg/bee LC50 (rainbow trout, 96-h) 0.48 mg/L
EC50 (daphnia magna, 48-h) 0.22 mg/L

Quinoclamine [2797-51-5]
Mammalian [1, 2, 459, 460]: References
1 C.D.S. Tomlin: The Pesticide Manual, 11th ed., British
LD50 (rat, oral) 2501600 mg/kg Crop Protection Council, Farnham, UK, 1997.
LD50 (mouse, oral) 12601350 mg/kg
2 http://sitem.herts.ac.uk/aeru/footprint/en/index.htm (ac-
LD50 (rat, dermal) >5000 mg/kg
cessed 2 December 2009).
LC50 (rat, 4-h inhalation) 0.320.79 mg/L air
Rabbit: irritating to eyes 3 http://toxnet.nlm,nih.gov/cgi-bin/sis/htmlgen?HSDB
Rabbit: nonirritating to skin (accessed 4 December 2009).
Guinea pig: not a sensitizer 4 U.S. EPA, HED Chapter for the Reregistration Eligibili-
Nonmutagenic ty Decision for Acifluorfen, 2002.
NOEL/NOAEL: 5 http://extonet.orst.edu/pips/gindex.html (accessed 30
Rat (2-year feed) 5.77.3 mg kg1 d1 November 2009).
Dog (2-year feed) 1.31.4 mg kg1 d1 6 Rohm & Haas, DE 2311638, 1973 (H.O. Bayer, C.
Rat (3-generation feed) 1.72.0
Swithenbank, R.Y. Yih).
Rat (teratogenicity, gavage) 5 mg kg1 d1
7 EU Commission, Aclonifen, SANCO/161/08-rev. 0,
(maternal)
Rat (teratogenicity, gavage) 75 mg kg1 d1 2008.
(developmental) 8 European Food Safety Authority (EFSA): Aclonifen,
ADI/AOEL 0.03 mg kg1 d1 Scientific Report 149 (2008) 180.
ADI (BRD) 0.002 mg kg1 d1 9 Rhone-Poulenc, DE 2831262, 1980 (W. Buck, R. Sehr-
ing, G. Linden, S. Lust).
10 T.R. Roberts, D.H. Hutson: Metabolic pathways of
agrochemicals, vol. 1, Royal Society of Chemistry,
Ecological [1, 2, 460]: Cambridge, UK, 1998.
11 M. Sumida, H. Kohno, K. Shonda, H. Fukami, T.
Tanaka, K. Wakabayashi, P. Boger, J. Pesticide Sci.
LD50 (bird, oral) 2000 mg/kg 21 (1996) 317.
LC50 (carp, 96-h) 0.063 mg/L 12 EU Commission: Bifenox, SANCO/3776/08-final,
EC50 (daphnia magna, 48-h) 2.15 mg/L
2009.
EC50 (algae, 72-h) 0.5 mg/L
LD50 (honeybee, contact) 0.75 mg/bee
13 European Food Safety Authority (EFSA): Bifenox,
LC50 (earthworm, 14-d) 188 mg/kg soil Scientific Report 119 (2007) 184.
14 Mobil Oil, DE 2019821, 1970 (R.Y. Theissen).
376 Weed Control, 2. Individual Herbicides
15 T. Yoshimoto, T. Fujita, T. Harayama, J. Pesticide Sci.
15 (1990) 341.
16 Ethoxyfen-ethyl, http://www.chinabaike.com/ (ac-
cessed 15 November 2009).
17 Budapesti Vegyimuvek, DE 3943015, 1990 (J. Bakos
et al.).
18 UK Advisory Committee on Pesticides, Evaluation of
Fluoroglycofen-ethyl, 50, 1992.
19 Rohm & Haas, EP 40898, 1981 (C.R. Downing, R.J.
Theissen, R.E. Holm).
20 U.S. EPA, Memorandum on Fomesafen, 4/25/06, 2006.
21 UK Advisory Committee on Pesticides, Evaluation of
Fomesafen, no. 118, 1995.
22 U.S. EPA, Fomesafen Summary Document for Regis-
tration Review: Initial Docket, 2007.
23 I.L. Adler, B.M. Jones, J.P. Wargo, J. Agric. Food Chem.
25 (1977) 1339.
24 U.S. EPA, Memorandum on Lactofen, 2000.
25 PPG, FR 2463119, 1981 (W.S. Grove).
26 Nitrofen, WHO Pesticide Data Sheet, no. 84, 1996.
27 Nitrofen, WHO/FAO Pesticide Residues in Food,
1983.
28 U.S. EPA, Risks of Oxyfluorfen Use to the Federally
threatened California Red-Legged Frog, 10/16/08, 2008.
29 U.S. EPA, Reregistration Eligibility Decision for Oxy-
fluorfen, 2002.
30 European Food Safety Authority (EFSA), Draft Assess-
ment Report on Oxyfluorfen, 07/11, 2007.
31 R.Y. Yih, C. Swithenbank, J. Agric. Food Chem. 23
(1975) 592.
32 EU Commission: Amidosulfuron, SANCO/1101/08-
rev.1, 2008.
33 European Food Safety Authority (EFSA): Amidosul-
furon, Scientific Report 116 (2007) 186.
34 AgrEvo, DE 3324802, 1985 (L. Willims, H. Mieden-
berger, K. Bauer, H. Burstell, H. Bieringer).
35 Azimsulfuron, FAO Specifications and Evaluations for
Agricultural Pesticides, 2004.
36 EU Commission, Azimsulfuron, SANCO/7591/VI/97-
final, 1999.
37 Du Pont, EP 204513, 1986 (G. Levitt).
38 European Food Safety Authority (EFSA): Bensulfur-
on-methyl, Scientific Report 178 (2008) 1102.
39 Du Pont, EP 51466, 1982 (R.F. Sauers).
40 U.S. EPA, Chlorimuron-ethyl (DPX F 6025) Herbicide
Profile, 4/86, 1986.
41 Du Pont, EP 5986, 1979 (G.D. Grantham, G. Levitt).
42 UK Advisory Committee on Pesticides, Evaluation of
Chlorsulfuron, no. 37, 1991.
43 European Food Safety Authority (EFSA): Chlorsufur-
on, Scientific Report 201 (2008) 1107.
44 U.S. EPA, Reregistration Eligibility Decision for Chlor-
sulfuron, 2005.
45 Du Pont, US 4169719, 1979 (G. Levitt).
46 Novartis, EP 44809, 1982 (W. Meyer, W. Fory).
47 Cyanamid, US 5009699, 1991 (T.E. Brady, M.E. Con-
don, P.-E. Marc).
48 Du Pont, EP 136061, 1985 (G. Aloysious).
Vol. 39
49 EU Commission: Ethoxysulfuron, SANCO/7461/
VI/-98-final, 2002.
50 AgrEvo, EP 342563, 1989 (L. Willims, K. Bauer, H.
Bieringer, H. Burstell).
51 EU Commission: Flazasulfuron, SANCO3051/99-fi-
nal, 2003.
52 Flazasulfuron, U.S. EPA Pesticide Fact Sheet, 2007.
53 Ishihara, EP 184385, 1986 (F. Kimura et al.).
54 W. Kramer, U. Schirmer: Modern Crop Protection
Compounds, Wiley-VCH, Weinheim 2007.
55 EU Commission: Flupyrsulfuron-methyl, SANCO/
5050/VI/97-final, 2001.
56 Du Pont, US 5393734, 1991 (T.A. Andrea, P.H. Liang).
57 Foramsulfuron, U.S. EPA Pesticide Fact Sheet, 2002.
58 Foramsulfuron, Canada Regulatory Note, REG 2003-08,
2008.
59 S. Yamamoto, T. Sato, Y. Iwasawa, F. Suzuki, T.I. Kai,
K. Suzuki, T. Nawamaki, J. Pesticide Sci. 15 (1990) 536.
60 N. Shimuzu, J. Sakamoto, H. Kamizono, K. Ohta, S.
Tashiro, J. Pesticide Sci. 21 (1996) 287.
61 Iodosulfuron-methyl-sodium, Canada Regulatory Note,
RD 2009-01, 2001.
62 Australian National Registration Authority for Agricul-
tural and Veterinary Chemicals: Evaluation of the New
Active Iodosulfuron-methyl-sodium in the Product Hus-
sar Selective Herbicide, 2001.
63 Australian National Registration Authority for Agricul-
tural and Veterinary Chemicals: Evaluation of the new
active Mesosulfuron-methyl in the Product Atlantis
Selective Herbicide, 2003.
64 Mesosulfuron-methyl, U.S. EPA Pesticide Fact Sheet,
2004.
65 AgrEvo, WO 9510507, 1995 (K. Lorenz et al.).
66 http://www.alanwood.net/pesticides/mesosulfuron.html
67 Metsulfuron-methyl, U.S. EPA Herbicide Profile, 3/86,
1986.
68 Metsulfuron-methyl; EU Commission: SANCO/7593/
VI/97-final, 2000.
69 Du Pont, EP 30139, ] 1981 (G. Levitt, W.C. Peterson).
70 EU Commission, Nicosulfuron, SANCO/3780/07-rev.1,
2008.
71 Nicosulfuron (Accent), U.S. EPA Chemical Fact Sheet,
6/90, 1990.
72 EFSA: Nicosulfuron, Scientific Report 120 (2007) 1
91.
73 Du Pont, EP 237292, 1987 (M.A. Hanagan).
74 Orthosulfamuron, U.S. EPA Pesticide Fact Sheet, 2007.
75 U.S. EPA, Orthosulfamuron Human Health Risk As-
sessment for proposed Use on Rice, 2007.
76 Novartis, EP 496701, 1992 (W. Meyer).
77 Primisulfuron-methyl, U.S. EPA Herbicide Pofile, 6/90,
1990.
78 Novartis, EP 72347, 1983 (W. Meyer, W. Fory).
79 http://alanwood.net/pesticides/propyrisulfuron.html
80 http://search.e-gov.go.jp/servlet/Public (accessed 2 De-
cember 2009).
81 EU Commission, Prosulfuron, SANCO/3055/99-final,
2002.
Vol. 39
82 Novartis, EP 120814, 1984 (W. Meyer, K. Ortle).
83 http://www.chinese-pesticide.com/herbicides/Pyrazo-
sulfuron-ethyl.htm.
84 http://chemicalland21.com/lifescience/agro/Pyrazosul-
furon-ethyl.htm
85 S. Kobayashi, Jpn. Pesti. Info 55 (1989) 17.
86 EFSA: Rinsulfuron, Scientific Report 45 (2005) 161.
87 FAO Specifications and Evaluations of Agricultural
Pesticides: Rimsulfuron, 2005.
88 Du Pont, EP 13480, 1978 (G. Levitt).
89 U.S. EPA Reregistration Eligibility Decision for Sulfo-
meturon, 2008.
90 Du Pont, EP 13481, 1980 (G. Levitt).
91 Takeda, EP 477808, 1992 (Y. Ishida, K. Otha, H.
Yoshikawa).
92 FAO Specifications and Evaluations for Plant Protection
Products: Thifensulfuron-methyl, 2000.
93 EU Commission: Thifensulfuron-methyl, SANCO/
7577/VI/07-final, 2002.
94 Du Pont, US 4448029, 1984 (G. Levitt).
95 EU Commision, Triasulfuron, SANCO/7589/VI/97-
final, 2000.
96 Novartis, EP 44808, 1982 (W. Meyer, W. Fory).
97 EU Commission, Tribenuron-methyl, SANCO/10671/
04-final, 2005.
98 U.S. EPA, Tribenuron-methyl Chemical Profile, 6/89,
1989.
99 Ishihara, EP 496608, ] 1992 (N. Sakashita et al.).
100 Australian National Registration Authority for Agricul-
tural and Veterinary Chemicals: Evaluation of the New
Active Trifloxysulfuron-sodium in the Product Envoke
Herbicide, 2002.
101 EU Commission, Triflusulfuron-methyl, SANCO/4439/
09-final, 2009.
102 Triflusulfuron-methyl, Canada Regulatory Note,
REG99-03, 1999.
103 EFSA: Triflusulfuron-methyl, Scientific Report 195
(2008) 1115.
104 Du Pont, WO 8909214, - 1989 (M.P. Moon).
105 EFSA: Tritosulfuron, EFSA Journal 62 (2007) 133.
106 EFSA: Acetochlor, Scientific Report 153 (2008) 1
130.
107 Monsanto, BE 622131, 1962 (J.F. Olin).
108 EFSA: Alahlor, EFSA Journal 111 (2004) 134.
109 Alachlor, WHO/FAO Pesticide Data Sheet, no. 86, 1996.
110 U.S. EPA, Reregistration Eligibility Decision for Ala-
chlor, 1998.
111 U.S. EPA, Diethatyl-ethyl (Antor) Herbicide Profile, 3/
85, 1985.
112 Th.A. Unger: Pesticide Synthesis Handbook, Noyes
Publication, Park Ridge, N.J., 1996.
113 EU Commission: Dimethachlor, SANCO/177/08-fi-
nal, 2009.
114 EFSA: Dimethachlor, Scientific Report 169 (2008) 1
111.
115 Novartis, DE 2305495, ] 1973 (C. Vogel).
116 EFSA: Metazachlor, Scientific Report 145 (2008) 1
132.
Weed Control, 2. Individual Herbicides 377
117 Metazachlor, FAO Specifications and Evaluatuoms for
Plant Protection Products, 1999.
118 BASF, DE 2648008, 1978 (K. Eicken, W. Rohr, B. Zeeh,
B. Wurzer).
119 U.S. EPA, Reregistration Eligibility Decision for S-
Metolachlor, 1995.
120 P.C. Hamm, A.J. Speziale, J. Agric. Food Chem. 4
(1956) 518.
121 Novartis, DE 2328340, 1973 (C. Vogel, R. Aebischer).
122 Propachlor, WHO/FAO Environmental Health Criteria
(EHC), no. 147, 1993.
123 Propachlor, WHO/FAO Pesticide Data Sheet, no.78,
1987.
124 Propachlor, WHO/FAO Health and Safety Guide, no. 77,
1992.
125 Monsanto, US 2863752, 1958 (P.C. Hamm, A.J.
Speziale).
126 Nitrok
emia, HU 53483, 1990 (J. Pelyva et al.).
127 Tokuyama, US 4802907, 1989 (T. Takematsu, S. Kato,
M. Ishizaki, T. Suyama).
128 U.S. EPA, Reregistration Eligibility Decision for Ame-
tryn, 2005.
129 Novartis, CH 337019, 1959 (H. Gysin, E. Knusli).
130 Atrazine, WHO/FAO: Pesticide Data Sheet, no. 82,
1996.
131 U.S. EPA, Interim Reregistration Eligibility Decision
for Atrazine, 2003.
132 Australian National Registration Authority for Agricul-
tural and Veterinary Chemicals: Technical Report on
Atrazine, 2002.
133 Novartis, CH 329277, 1958 (H. Gysin, E. Knusli).
134 Deutsche Gold- und Silber-Scheideanstalt, GB 1132306,
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135 Novartis, ZA 6802977, ] 1968 (E. Nikles).
136 Indazifam, http://www.farmchemicalsinternational.com/
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137 U.S. EPA, Prometon (Pramitol) Herbicide Profile, 2/85,
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138 U.S. EPA, Propazine (Milocep) Herbicide Profile, 12/88,
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139 H. Gysin, E. Knusli, Advance Pest. Control Res. 3 (1960)
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140 U.S. EPA, Reregistration Eligibility Decision for Sima-
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141 UK Advisory Committee on Pesticides, Evaluation on
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143 Novartis, GB 814947, 1959.
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146 Novartis, CH 329277, 1958 (H. Gysin, E. Knusli).
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147 Novartis, FR 1325926, 1963.
148 Novartis, DE 1905598, 1969 (H. Martin, S. Janiak, W.
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149 Cumyluron, http://www.lookchem.com/cas-994/99485-
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150 Cumyluron, http://agropages.com/database/identifica-
tion.aspx?charn&id3328comcumyluron (acces-
sed 16 October 2009).
151 Showa Denko, JP 7335454, 1973 (T. Takematsu et al.).
152 Rhone-Poulenc, DE 2101938, 1970 (R. Boesch).
153 Australian National Registration Authority for Agricul-
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154 H.C. Bucha, C.W. Todd, Science 114 (1951) 493.
155 U.S. EPA, Reregistration Eligibility Decision for Fluo-
meturon, 2005.
156 Novartis, GB 914779, ] 1963.
157 EU Commission: Isoproturon, SANCO/3045/99-fi- 192 Imazamox, U.S. EPA Pesticide Fact Sheet, 1997.
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158 Novartis, GB 1407587, 1975.
159 Shionogi, JP 7886033, 1978 (H. Yikinaga, S. Sumimoto,
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160 U.S. EPA, Reregistration Eligibility Decision for Linur-
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161 EU Commission, Linurons, SANCO/7595/VI/97-final,
2002.
162 K. Hartel, Mededel. Fac. Landbouwwet. Rijksuniv. Gent
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163 Bayer, GB 1085430, 1967 (H. Hack, L. Eue, W.
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165 W. Berg, Pflanzenkr. Pflanzenpath. Pflanzensch. 75
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168 U.S. EPA, Reregistration Eligibility Decision for Sidur-
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169 Du Pont, US 3309192, 1967 (R.W. Luckenbough).
170 U.S. EPA, Tebuthiuron (Graslan, Spike) Herbicide Pro-
file, 2/85, 1985.
171 DowElanco, DE 1912543, 1969 (T. Cebelo, R. Walde).
172 U.S. EPA, Reregistration Eligibility Decision for Thi-
diazuron, 2005.
173 U.S. EPA, Reregistration Eligibility Decision for Ben-
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174 EFSA: Benfluralin, Scientific Report 127 (2008) 1 208 J. Pokorny, J. Am. Chem. Soc. 66 (1941) 768.
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175 DowElanco, US 3257190, 1966 (Q.F. Soper).
176 Anchem, DE 2058201, 1971.
177 Wacker, DE 2013509, 1970 (D.L. Hunter, C.W. Lefevre,
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178 U.S. EPA, Reregistration Eligibility Decision for Ethal-
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179 DowElanco, US 3257190, 1966 (Q.F. Soper).
Vol. 39
180 BASF, ZA 6808409, 1969 (K. Kiehs, K.H. Konig, A.
Fischler).
181 U.S. EPA, Reregistration Eligibility Decision for Ory-
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182 DowElanco, US 3367949, 1968 (Q. F. Soper).
183 EU Commission, Pendimethalin, SANCO 7477/VI/98-
final, 2003.
184 U.S. EPA, Reregistration Eligibility Decision for Pen-
dimethalin, 1997.
185 Cyanamid, DE 2241408, 1973 (A.W. Lutz, R.E. Diehl).
186 Novartis, US 3 966 816, 1976 (W. Woods, D.L. Hunter).
187 U.S. EPA, Reregistration Eligibility Decision for Triflu-
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188 EFSA: Trifluralin, Scientific Report 28 (2005) 177.
189 DowElanco, US 3257190, 1966 (Q.F. Soper).
190 U.S. EPA, HED Chapter of the Tolerance Reassessment
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191 Novartis, EP 233150, 1987 (H. Szczepansk, D. Durr).
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194 U.S. EPA, Reregistration Eligibility Decision for Im-
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195 D.W. Ladner, Pestic. Sci. 29 (1990) 317.
196 U.S. EPA, Tolerance Reassessment Eligibility Risk
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197 Novartis, NL 6600834, 1966.
198 EU Commission, Clodinafop-propargyl, SANCO/
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199 Clodinafop-propargyl, U.S. EPA Pesticide Fact Sheet,
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200 http://evv.gov.jp/water/sui-kaitei/kijum/rv/koz_clome-
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204 2,4-D, WHO/FAO Pesticide Data Sheet, no. 37, 1978.
205 2,4-D, WHO Environmental Health Criteria, no. 29,
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206 U.S. EPA, Reregistration Eligibility Decision for 2,4-D,
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209 U.S. EPA, Reregistration Eligibility Decision for 2,4-
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210 EU Commission: 2,4-DB, SANCO/7601/VI/97-final,
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211 2,4-DB, FAO Specifications for Plant Protection Pro-
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212 M.E. Synerholm, P.W. Zimmermann, Contr. Boyce
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Vol. 39
213 Dichlorprop, FAO Specifications for Plant Protection
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215 U.S. EPA, Reregistration Eligibility Decision for Di-
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216 EU Commission: Dichlorprop-P, SANCO/10016/
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217 EFSA: Dichlorprop-P, Scietific Report 52 (2005) 1
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218 W.O.G. Nuykken, B.H. Menck, E. Haden, Mededel.
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219 U.S. EPA, Reregistration Eligibility Decision for Diclo-
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220 AgrEvo, DE 2223894, 1973 (W. Becker, L.H. Peter, H.
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221 EFSA: Fenoxaprop-P-ethyl, Scientific Report 121
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222 EU Commission: Fenoxaprop-P-ethyl, SANCO/
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223 U.S. EPA, Fluazifop-P-butyl: Revised HED Chapter of
the Tolerance Reassessment Eligibility Document
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224 EU Commission: Haloxyfop-P/R, SANCO/10036/
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225 EFSA: Haloxyfop-P/R, Scientific Report 87 (2006)
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226 U.S. EPA, Reregistration Eligibility Decision for
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227 EU Commission: MCPA, SANCO/4062/2001-final,
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230 U.S. EPA, Reregistration Eligibility Decision for MCPB
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231 EU Commission: MCPB, SANCO/4063/2001-final,
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232 Zeneca, GB 804505, 1958 (G.W. Kitchingman, A.C.
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233 Mecoprop, U.S. EPA Pesticide Fact Sheet, no. 192,
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234 EU Commission: Mecoprop, SANCO/3063/99-final,
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235 U.S. EPA, Reregistration Eligibility Decision for Me-
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236 EU Commission: Mecoprop-P, SANCO/3065/99-fi-
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237 H.J. Nestler, H. Bieringer, Z. Naturforsch. B 85 (1980)
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239 EFSA: Propaquizafop, Scientific Report 204 (2008)
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240 Novartis, EP 52798, 1982 (G. Frater, M. Suchy, J.
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241 EU Commission: Quizalofop-P-ethyl, SANCO/169/
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242 EFSA: Quizalofop-P-ethyl, EFSA Scientific Report
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243 2,4,5,-T,WHO/FAO Data Sheets on Pesticides, no.13,
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244 U.S. EPA: Amicarbazone: HED Human Health Risk
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245 Bayer, DE 3839206, 1990 (K.H. Muller et al.).
246 EU Commission: Amitrole, SANCO/6839/VI/97-fi-
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247 Amitrole, WHO/FAO Environmental Health Criteria,
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248 Amitrole, WHO/FAO Data Sheet on Pesticides, no. 79,
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249 A. Kroller, Residue Rev. 12 (1966) 163.
250 Du Pont, DE 2801429, 1978 (A.D. Wolf).
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253 Australian National Registration Authority for Agricul-
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active Carfentrazone, 2000.
254 Carfentrazone, U.S. EPA Pesticide Fact Sheet, 1998.
255 FMC, WO 90021120, 1990 (K.M. Poss).
256 Cloransulam-methyl, U.S. EPA Pesticide Fact Sheet,
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257 DowElanco, US 5163995, 1995 (J.C. van Heertum, B.C.
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258 V.A. Petrov: Fluorinated Heterocyclic Compounds:
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259 EU Commission: Florasulam, SANCO/1406/2001-
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260 Florasulam, Canada REG 2001-12.
261 Florasulam, U.S. EPA Pesticide Fact Sheet, 2007.
262 Flucarbazone-sodium, U.S. EPA Pesticide Fact Sheet,
2000.
263 U.S. EPA, Revised Phase2 HED Chapter of the Toler-
ance Reassessment Eligibility Decision Document for
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264 U.S. EPA, Flumetsulam Registration Review: Ecologi-
cal Risk Assessment Problem Formulation, 2008.
265 Flumetsulam, U.S. EPA Amended Human Health As-
sessment Scoping Document in Support of Regestration
Review, 2008.
266 Kureha, EP 282303, 1988 (T. Shida et al.).
267 M. Snel, P. Watson, N.R. Gray, W.A. Kleschick, C.M.
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268 EFSA: Penoxsulam, Scientific Report 343 (2009) 1
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269 Penoxsulam, U.S. EPA Pesticide Fact Sheet, 2004.
270 Propoxycarbazone-sodium, U.S. EPA Pesticide Fact
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271 Pyroxsulam, U.S. EPA Pesticide Fact Sheet, 2008.
380 Weed Control, 2. Individual Herbicides
272 U.S. EPA, Pyroxsulam Human Health Assessment for
Proposed Uses on Wheat, 2007.
273 Sulfentrazone, U.S. EPA Pesticide Fact Sheet, 2004.
274 Sulfentrazone, U.S. EPA Revised Human Health As-
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275 U.S. EPA, Environmental Fate and Ecological Risk
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276 S. Selgel, G. Theodoridis: Synthesis of Benfendizone,
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277 U.S. EPA, Bromacil (Hyvarx X, XL) Herbicide Profile,
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278 B.C. Bucha, W.E. Cuoery, J.H. Harrod, H.M. Loux, L.
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279 Australian National Registration Authority for Agricul-
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280 EU Commision, Lenacil, SANCO/833/09-rev. 3, 2008.
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282 Du Pont, US 3235357, 1962.
283 U.S. EPA, Terbacil Herbicide Profile, 8/89, 1989.
284 Aminopyralid, U.S. EPA Pesticide Fact Sheet, 2005.
285 Dow AgroSciences: Aminopyralid, www.dowagro.com
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286 DowElanco, US 3285925, 1966 (H.A. Johnston, M.S.
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287 EU Commission: Clopyralid, SANCO/10012/2006-
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288 Dow Elanco, US 3317549, 1963 (H. Johnston).
289 UK Advisory Committee on Pesticides, Evaluation of
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290 EU Commission: Diflufenican, SANCO/3782/08-
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291 Rhone-Poulenc, EP 53011, 1982 (M.C. Cramp, J. Gil-
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292 BASF, JP 6245570, 1987.
293 D.P. Ward: Summary of Toxicology Studies with
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294 Monsanto, EP 133612, 1985 (L.F. Lee).
295 EU Commission: Review report of the active substance
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296 Fluroxypyr, U.S. EPA Pesticide Fact Sheet, 1998.
297 DowElanco, US 4110104, 1978 (S.D. McGregor).
298 U.S. EPA: Picloram (Tordon, Grazan) Herbicide Profile
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299 EU Commission: Picloram, SANCO/835/08-rev. 2.
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300 EU Commission: Picolinafen, SANCO/ 1418/2001-
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301 Australian National Registration Authority for Agricul-
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302 Shell, EP 4470041991 (C.J. Foster et al.).
303 Thiazopyr, U.S. EPA Pesticide Fact Sheet, 1997.
Vol. 39
304 Monsanto, EP 278944, 1988 (L.F. Lee, Y. L. L. Sing).
305 EU Commission: Triclopyr, SANCO/10010/2006-
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306 DowElanco, US 3862952, 1975 (L.D. Markley).
307 U.S. EPA, Reregistration Eligibility Decision for Asu-
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310 W.G. Templeman, W.A. Saxton, Nature 156 (1945)
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311 Rhone-Poulenc, FR 1249434, 1959 (J. Metivier).
312 U.S. EPA, Reregistration Eligibility Decision for Chlor-
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313 EU Commission: Chlorpropham, SANCO/3041/99-
final, 2003.
314 Columbia, US 2695225, 1954 (E.D. Witman).
315 U.S. EPA, Reregistration Eligibilty Decision for Cyclo-
ate, 2004.
317 U.S. EPA, Reregistration Eligibility Decision for Des-
medipham, 1996.
318 EU Commission, Desmedipham, SANCO/4061/2001-
final, 2004.
319 AgrEvo, NL 6604363, 1966.
320 Zeneca, US 2913327, 1959 (H. Tilles, J. Antognini).
321 EU Commision: Molinate, SANCO/3047/99-final,
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322 U.S. EPA, Review of 60-Day Comments and Revised
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323 Zeneca, US 3198786, 1965 (H. Tilles, R. Curtis).
324 U.S. EPA, Reregistration Eligibility Decision or Pebu-
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325 Zeneca, US 3185720, 1957 (H. Tilles, J. Antognini).
326 U.S. EPA, Phenmedipham-methyl (Betanal, Spin-Aid)
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327 EU Commision: Phenmedipham, SANCO/4060/
2001-final, 2004.
328 U. S. EPA, Prpham (Chem Hoe) Herbicide Profile, 2/85,
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329 W.G. Tempelman: Effect of Some Arylcarbamic Es-
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330 EU Commision: Prosulfocarb, SANCO/2824/07-rev.
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331 EFSA: Prosulfocarb, Scientific Report 111 (2007) 1
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332 K. Tsuzuki, Jpn. Pestic. Info 57 (1990) 30.
333 EU Commission: Triallate, SANCO/4437/09-final,
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334 U.S. EPA, Reregistration Eligibility Decision for Trial-
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335 EFSA: TriLLATE, Scientific Report 181 (2008) 1
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336 H.C. Bucha, C.W. Todd, Science 114 (1951) 493.
337 AgrEvo, PI 7804448, 1979 (N.R. Patel).
Vol. 39
338 U.S. EPA, Reregistration Eligibility Decision for ben-
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339 Zeneca, US 3205253, 1965 (L.W. Fancher, C.L.
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340 S. Mase, Jpn. Pestic. Info 45 (1984) 27.
341 Sumitomo, DE 2147873, 1972 (T. Satomi et al.).
342 AgrEvo, JP 7391019, 1973 (Y. Inoue, T. Nida).
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344 Novartis, DE 1812497, 1969 (E. Topfl).
345 A. Formigomi, Y. Horono, Mededel. Fac. Landbouw-
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346 Zeneca, WO 9221649, 1992 (J.D. Jones).
347 Nippon Soda, DE 2822304, 1978 (I. Iwataki, H. Shibuya,
H. Ishikawa, T. Kawana).
348 BASF, DE 3121355, 1982 (R. Becker, D. John, W. Rohr,
W. Himmele, H. Siegel, B. Wurster).
349 EU Commission: Tepraloxydim, SANCO/10388/
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350 BASF, DE 4222261, 1993 (J. Kast et al.).
351 EFSA: Trakoxydim, Scientific Report 139 (2008) 1
78.
352 Zeneca, EP 80301, 1983 (R.W. Warner et al.).
353 EU Commission: Bromoxynil, SANCO/4347/2000-
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354 K. Carpenter, B.J. Heywood, R.L. Wain, Nature 200
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355 B.C. Sharman, Nature 186 (1960) 89.
356 EU Commission: Ioxynil, SANCO/4349/2000-final,
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357 http://mitsui-agro.com/product/pdf/msds-22271.pdf.
358 http://www.env.go.jp/water/sui-katei/kijun/rv/h02-pyr-
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359 Du Pont, US 3 897 429, 1975 (F. R. Haglid).
360 EFSA: Metamitron, Scientific Report 185 (2008) 1
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361 Bayer, DE 2107757, 1972 (K. Dickore, W. Draber, L.
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362 EFSA: Metribuzin, Scientific Report 88 (2006) 174.
363 A. Dornow, H. Manzel, P. Marx, Ber. 97 (1964) 2173.
364 U.S. EPA, Allidochlor (Randox) Herbicide Profile, 3/85,
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365 Spezial Hamm, J. Am. Chem. Soc. 78 (1956) 2556.
366 EU Commission: Beflubutamid, SANCO/T13/07-
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367 EFSA: Dimethenamid, Scientific Report 53 (2005) 1 398 A. van Almsick, J. Benet-Buchholz, B. Olemik, L.
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368 BASF, DE 3303388, 1983 (K. Seckinger, F. Kuhnen, K.
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369 EU Commission: Dimethenamid-P, SANCO/1402/
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370 Eli Lily Co., US 3120434, 1960 (E.F. Alders et al.).
371 EU Commission: Napropamide, SANCO/112/08,
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372 Stauffer, US 3480671, 1969 (H. Files et al.).
373 U.S. EPA, Reregistration Eligibility Decision for Nap-
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374 EU Commission: Pethoxamid, SANCO/10396/2002-
rev. 1, 2006.
Weed Control, 2. Individual Herbicides 381
375 EU Commission: Propyzamide, SANCO/6502/VI/
99-final, 2007.
376 EU Commission: Flufenacet, SANCO/7469/VI/98-
final, 2003.
377 Flufenacet, U.S. EPA Pesticide Fact Sheet, 1998.
378 H. Foster, R.R. Schmidt, H.J. Santel, R. Andree, Pflan-
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379 U.S. EPA, Reregistration Eligibility Decision for Me-
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380 U.S. EPA, Chemicl Fact Sheet for Perfluidone, 1985.
381 U.S. EPA, Reregistration Eligibility Decision dor Pro-
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382 EU Commission, Propanil, SANCO/ 352/08-rev. 0,
2008.
383 Kumiai, EP 321 846, 1989 (N. Wada, S. Kusano, Y.
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384 EU Commission: Clorthal-methyl, SANCO/1336/08-
final, 2009.
385 EU Commission: Dicamba, SANCO/829/08-rev.,
2008.
386 U.S. EPA, Correction to the Amendments to the Dicam-
ba RED, 2009.
387 Novartis, US 3013054, 1958 (S. B. Richter).
388 M. Takamura, K. Kawano, R. Hanai, Y. Kimura: Dis-
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389 Y. Nezu, N. Wada, Y. Saitoh, S. Takahashi, T. Miya-
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390 U.S. EPA, Quiclorac Summary Registration Review:
Initial Docket, 2007.
391 EU Commission: Mesotrione, SANCO/1416/2001-
final, 2003.
392 H. Adachi, A. Ueda, T. Aihara, K. Tomida, T. Kawana,
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393 EU Commission: Sulcotrione, SANCO/ 159/ 08-final,
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394 EFSA: Sulcotrione, Scietific Report 150 (2008) 186.
395 http://www.env.go.jp/water/sui-kaitei/kjun/rv/t003_te-
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396 http://www.fsc.go.jp/iinkai/i-dai274/dai274pdfkai-sir-
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397 Tembotrione, U.S. EPA Pesticide Fact Sheet, 2007.
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399 http://baike.china.alibaba.com/doc/review-d2322360.
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400 EU Commission: Ethofumesate, SANCO/6503/VI/
99-final, 2002.
401 U.S. EPA, Reregistration Eligibility Decision for Etho-
fumesate, 2005.
402 EU Commission: Cinidon-ethyl, SANCO/6498/VI/
99-final, 2002.
403 Sumitomo, EP 83055, 1983 (E. Nagano et al.).
404 Flumioxazin, U.S. EPA Pesticide Fact Sheet, 2001.
382 Weed Control, 2. Individual Herbicides
405 U.S. EPA, HED Risk Assessment for Phase III of the
Reregistration Eligibility Decision or Flumioxazin,
2005.
406 Ming-Li Huang et al.: Synthesis and Herbicidal Activ-
ity of 2-(7-Fluoro-3-oxo-3,4-dihydro-2H-benzo[1,4],
oxazin-6-yl)isoindoline-1,3-dione, J. Agric. Food
Chem. 53 (2005) 79087914.
407 U.S. EPA, Dinoseb (Premerge, Dinitro) Herbicide Pro-
file, 4/87, 1987.
408 DowElanco, US 2642354, 1953 (K.C. Barrons).
409 H.L. Albert, J.F. Charles, J. Am. Chem. Soc. 76 (1954)
479.
410 Iodomethane, U.S. EPA Pesticide Fact Sheet, 2007.
411 U.S. EPA, Reregistration Eligibility Decision for
Methylbromide, 2008.
412 U.S. EPA, Ammonium Sulfamate (ammate) Herbicide
Profile, 3/85, 1985.
413 U.S. EPA, Reregistration Eligibility Decision for Sodi-
um Chlorate, 2006.
414 EU Commission, Oxadiargyl, SANCO & 3053/99-final,
2003.
415 http://202.194.11.26:8001/xwlw/detail.jsp?
channelid65194&record5 (accessed 22 November
2009).
416 U.S. EPA, Isoxaben Summary Document Registration
Review Docket, 2007.
417 Eli Lily, GB 2084140, 1982 (K.W. Burow).
418 EU Commission: Isoxaflutole, SANCO/ 3136/99-fi- 445 U.S. EPA, Clomazone-Acute and Chronic Dietary Ex-
nal, 2003.
419 Isoxaflutole, U.S. EPA Pesticide Fact Sheet, 1998.
420 Rhone-Poulenc, EP 527036, 1993 (P.A. Cain, S.M.
Cramp, G.M. Little, B. M. Lascombe).
421 U.S. EPA, Human Health Risk Assessment for New
Active Ingredient Topramazone, 1998.
422 Benzofenap, http://www.chemyq.com/En/xz/xz5/
41037vyngi.htm (accessed 4 September 2009).
423 Y. Miura, T. Mabuchi, M. Higashimura, T. Amanuma:
Development of a New Herbicide, Pyraflufen-ethyl, 449 U.S. EPA, Chemical Fact Sheet for Fluridone, no. 81,
J. Pestic. Sci. 28 (2003) 219220.
424 Pinoxaden, U.S. EPA Pesticide Fact Sheet, 2005.
425 U. Hofer, M. Muehlebach, S. Hole, A. Zoschke: Pi-
noxaden, J. Plant Disease Protection, Special Issue
XX, 2006, 989995.
426 EU Commission: Pyraflufen-ethyl, SANCO/3039/ 451 A.A. Abdelselam, K.N. Winzenberg: Preparation of 1-
99-final, 2002.
427 Pyrasulfotole, U.S. EPA Pesticide Fact Sheet, 2007.
428 M.H. Schmitt, A. van Almsick, L. Wilems: Discovery
and Chemistry of Pyrasulfotole, a New Dicot Herbicide
for Cereal Production, Pflanzenschutz-Nachrichten
Bayer 61 (2008) 714.
429 T.R. Roberts, D.H. Hudson, P.W. Lee, P.H. Nicholls, J.
R. Plimmer (eds.): Metabolic Pathways of Agrochem-
icals, parts 1 and 2, , Royal Society of Chemistry,
Cambridge 1999.
430 Pyrazolinate, http://www.jaish-gr.jp/anzen/gmsds/
58011-68-v.html (accessed 23 November 2009).
431 Pyrazolinate, http://www.chemicalbook.com/ (accessed
25 November 2009).
Vol. 39
432 Parazoxyfen, http://www.chinabaike.com/ (accessed 8
December 2009).
433 EU Commission, Pyridate, SANCO/7576/VI/97-final,
2001.
434 Novartis, DE 2331398, 1975 (R. Schoenbeck, E. Kloim-
stein, H. Mayer, A. Diskus, E. Auer).
435 EFSA: Chloridazon, Scientific Report 108 (2007) 182.
436 U.S. EPA, Reregistration Eligibility Decision for Nor-
flurazon, Case 0229.
437 U.S. EPA, Reregistration Eligibility Decision for Difen-
zoquat, 1994.
438 U.S. EPA, Reregistration Eligibility Decision for Acro-
lein, 2008.
439 Acrolein, WHO/FAO Health and Safety Guide, no. 67,
1991.
440 Acrolein, WHO/FAO Environmental Health Criteria,
no. 127, 1992.
441 Acrolein, WHO/UNEP/ILO Concise International
Chemical Assesment Document (CICAD), no. 43, 2002.
442 M. Jaequemijs, J.F.C. Stavenuiter, G. Zomer: Benta-
tone, Labaratory Compounds and Radiopharmaceuti-
cals 28 (2006) 12291232.
443 K. Sekino, Y. Yamada, H. Koyamagi, S. Nakahara,
Discovery and Development of a New Herbicide Ben-
zobicyclon, J. Pestic. Sci. 34 (2009) 113114.
444 U.S. EPA, Reregistration Eligibility Decision for Chlor-
flurenol-methyl, 2007.
posure Analysis, 2008.
446 Tang Dexin, Weidong, Xutao Zhuang: Synthesis Tech-
nique of Clomazone and Its Application to Increase the
Quality, Modern Pesticide Modern Agrochem. 1
(2002) 2032.
447 U.S. EPA, Endothal: HED Chapter of the Reregistration
Eligibility Decision Document, 2005.
448 U.S. EPA, Human Health Risk Assessment for Fluri-
done, 2004.
1986; http://pmep.cce.cornell.edu/ (accessed 6 Decem-
ber 2009).
450 T.W. Waldrep, H.M. Taylor: 1-Methyl-3-phenyl-5-[3-
(trifluoromethyl)phenyl-4(1H)-pyridinone, a New Her-
bicide, Agric. Food Chem. 24 (1976) 12501251.
[(3-Trifluoromethyl)phenyl-3,4-dihydro-2-(1H)-pyridi-
none Derivatives from Azaannulation Reactions of N-
[(3-trifluoromethyl)phenyl-Substitited Enaminones
Austr. J. Chem. 58 (2005) 870876.
452 UK Advisory Committee on Pesticides, Evaluation of
Flurtamone, no. 196, 2000.
453 EU Commission, Flurtamone, SANCO/10162/2003-fi-
nal, 2003.
454 Fluthiacet-methyl, U.S. EPA Pesticide Fact Sheet, 1999.
455 Y. Sato, T. Hoshi, T. Iida, C. Ogino, B. Nicolaus, K.
Wakabayashi, P. Boger, Z. Naturforsch. 49 (1994) 49.
456 Agri Business Division Carban Co, Ltd., Mitsubishi
Chemical Biology: Summary of Toxicity Studies on
Indanofan, J. Pestic. Sci. 26 (2001) 327333.
Vol. 39
457 A. Hosakawa, T. Shike, M. Katsurada, O. Ikeda, N.
Minami, T. Jikihara: Synthesis and herbicidal activity
of Indanofan and related 2-(2-phenyloxiran-2-ylmethl)
indan-1,3-dione derivatives, J. Pestic. Sci. 26 (2001)
4147.
458 H. Suzuki, K. Jikihara, M. Sonoda, Y. Usui: Develop-
ment of a New Herbicide: Oxaziclomefone, J. Pestic.
Sci. 28 (2003) 221222.
459 EU Commission, Quinoclamine, SANCO/ 3622/07-rev.
1, 2008.
460 EFSA: Quinoclamine, Scientific Report 117 (2007)
170.
461 EU Commission, Current Status of Active Substances as
Regards Directive 91/414/EEC, SANCO/E3; http://ec.euro-
pa.eu/food/plant/protection/evaluation/3010_rev_181208.
xls (accessed 13 October 2009).
462 W. H. Ahrens (ed.): Herbicide Handbook, 7th ed., Weed
Science Society of America, Champaign, IL., 1994.
463 Fomesafen, U.S. Federal Register 62 (1997) 61639
61645.
464 Lactofen U.S. Federal Register 72 (2007) 33901
33907.
465 U.S. EPA, Lactofen Summary Document Registration
Review: Initial Docket, 2007.
466 U.S. EPA, Integrated Risk Information System (IRIS);
http://www.epa.gov./iris (accessed 2 November 2009).
467 U.S. EPA, Bensulfuron-methyl Pesticide Tolerance, 2/
98, 1998.
468 Chlorimuron-ethyl, U.S. Federal Register 63 (1998)
1891218919.
469 http://www.chinese-pesticide.comherbicides/cinosul-
furon (accessed 27 November 2009).
470 Novartis Nippon, J. Pesticide Sci. 17 (1992) 165.
471 http://apvma.gov.au/chemrev/Reviews.shtml.
472 Ethametsulfuron-methyl, U.S. Federal Register 66
(2001) 1820118207.
473 Halosulfuron-methyl, U.S. Federal Register 67
(2002) 5918259193.
474 Takeda, J. Pesticide Sci. 20 (1995) 381.
475 Iodosulfuron, U.S. Federal Register 67 (2002)
5752157531.
476 Nicosulfuron, U.S. Federal Register 61 (1996) 4 399.
477 U.S. EPA, Environmental Fate and Ecological Risk
Assessment for the Registration of Orthosulfuron, 2007.
478 Primisulfuron-methyl, U.S. Federal Register 62
(1997) 6601466020.
479 Prosulfuron, U.S. Federal Register 67 (2002) 79914
79918.
480 PAN Pesticide Database, http://www.pesticideinfo.org/
Search_Chemicals.jsp (accessed 25 November 2009).
481 Du Pont Nippon: Rimsulfuron, J. Pesticide Sci. 22
(1997) 356.
482 Sulfosulfuron U.S. Federal Register 62 (1997)
6608366091.
483 Du Pont Nippon: Thifensulfuron-methyl, J. Pesticide
Sci. 18 (1993) 219.
484 Thifensulfuron-methyl, U.S. Federal Register 72
(2007) 1317913184.
Weed Control, 2. Individual Herbicides 383
485 Triasulfuron, U.S. Federal Register 63 (1998) 44146
44152.
486 Trifloxysulfuron-methyl, U.S. Federal Register 68
(2003) 1392413930, id. 5437754386.
487 Acetochlor, U.S. Federal Register 65 (2000) 3682
3690.
488 S-Metolachlor, U.S. Federal Register 68 (2003)
1594515958.
489 Novartis Nippon: Pretilachlor, J. Pesticide Sci. 11
(1986) 132.
490 U.S. EPA, Reregistration Eligibility Decision for Pro-
pisochlor, 1988.
491 - Propachlor, WHO Environmental Health Criteria,
no.147, 1993.
492 Novartis Nippon, J. Pesticide Sci. 18 (1993) 213.
493 U.S. EPA, Decision Documents for Atrazine, 2008.
494 Acceptable Daily Intakes, Acute Reference Doses,
Short-Term and Long-Term Dietary Intakes, Joint
FAO/WHO Meeting on Pesticide Residues, Rome 2008.
495 http://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.
htm (accessed 22 November 2009).
496 U.S. EPA, Reregistration Eligibility Decision for Pro-
meton, 2008.
497 Prometryn, U.S. Federal Register 63 (1998) 94949499.
498 Propazine, U.S. Federal Register 70 (2005) 36159
36164.
499 Nippon Nohyaku/Novartis: Simazine, J. Pesticide
Sci. 17 (1986) 315.
500 EU Commission: Chlorbromuron, SANCO/4329/
2000-final, 2005.
501 Chlortoluron in Drinking Water, WHO/SDE/WSH/
03.04/33, 2003.
502 U.S. EPA, Chloroxuron (Tenoran) Herbicide Profile, 2/
85, 1985.
503 Japanese Ministery of Agriculture, Farming and Fisher-
ies, http://search.e-gov.go.jp/servlet/Public/?CLASS-
NAMEPcm103&btn (accessed 28 November 2009).
504 Diuron, EFSA Scientific Report 25 (2005) 158.
505 Shionogi: Isouron, J. Pesticide Sci. 11 (1986) 131.
506 Ethalfluralin, U.S. Federal Register 66 (2001) 57082
57086.
507 U.S. EPA, Profluralin (Tolban) Herbicide Profile, 3/85,
1985.
508 Imazapic, U.S. Federal Register 66 (2001)
6632566333.
509 Bromofenoxim, http://www.foodmate.net (accessed 10
December 2009).
510 Cyhalofop-butyl, U.S. Federal Register 74 (2009)
1587615880.
511 2,4-D, Joint FAO/WHO Meeting of Experts on Pesti-
cide Residues in Food 4. 7 (1996) 4150.
512 Fenoxaprop-ethyl, U.S. Federal Register 63 (1998)
1982919837.
513 U.S. EPA, Fenoxyprop-P-ethyl Summary Document
Registration Review: Initial Docket, 2007.
514 U.S. EPA, Revised Acute and Chronic Dietary Exposure
Assessment for the Tolerance Reassessment Eligibility
Decision for Fluazifop-butyl, 2004.
384 Weed Control, 2. Individual Herbicides
515 U.S. EPA, Fluazifop-butyl/Fluazifop-P-butyl : Report of
the Hazard Identification Assessment Review Commit-
tee, 2004.
516 FAO Specifications and Evaluation of Plant Protection
Products: Fluzifop-P-butyl, 2000.
517 Haloxyfop (including Haloxyfop-P- and Haloxyfop-R
methyl esters), Joint FAO/WHO Meeting, Rome
2006, 315354.
518 U.S. EPA, Reregistration Eligibility Decision for
MCPB, and Salts, 2006.
519 Quizalofop-ethyl, U.S. Federal Register 69 (2004)
5225652261.
520 Quizalofop-ethyl, U.S. Federal Register 61 (1996)
3107931081.
521 U.S. EPA, Quizalofop-P-ethyl (Assure, super) Pesticide
Petition Filing, 12/97, 1997.
522 2,4,5-T, WHO/FAO Pesticide Residues in Food, 1981.
523 Amicarbazone, U.S. EPA Pesticide Fact Sheet, 2005.
524 Azafenidin, U.S. Federal Register 64 (1999) 59767
59771.
525 Diclosulam, U.S. Federal Register 65 (2000) 12129
12134.
526 Flucarbazone, U.S. Federal Register 70 (2005)
4341243417.
527 Penoxsulam, U.S. Federal Register 74 (2009) 18644
18648.
528 Propoxycarbazone, U.S. Federal Register 69 (2004)
4077440781.
529 U.S. EPA, Environmental Fate and Ecological Risk
Assessment for the Registration of Pyroxsulam, 2008.
530 U.S. EPA, Revised EFED Probable Formulation for
Sulfentrazone Registration Review, 2009.
531 Thiencarbazone, U.S. Federal Register 73 (2008)
6096360969.
532 Bromacil, U.S. EPA Health Advisory, 1998.
533 Butafenacil, U.S. Federal Register 68 (2003) 8896
8900.
534 Terbacil, U.S. Federal Register 70 (2005) 53180
53185.
535 Aminopyralid, U.S. Federal Register 70 (2005)
4641946428.
536 Clopyralid, U.S. Federal Register 66 (2001) 2308
2316.
537 Defenzopyr, U.S. Federal Register 64 (1999) 4301
4308.
538 Rohm & Haas Nippon: Dithiopyr, J. Pesticide Sci. 18
(1993) 91.
539 Dithiopyr, U.S. Federal Register 59 (1994) January
12.
540 Rohm & Haas: Dithiopyr, MSDS 02/15/01 Philadel-
phia 2001.
541 Picloran, Canada Regulatory Note REG 2003-02.
(accessed)
542 US National Information Center, Thiazopyr, Technical
Fact Sheet, http://www.ipmcenters.org.ecotox (accessed
14 July 2010).
543 Triclopyr, U.S. Federal Register 67 (2002) 58712
58725.
Vol. 39
544 Butylate, U.S. Federal Register 66 (2001) 47219
47222.
545 Karbutilate, U.S. Federal Register 69 (2004) 53040
53044; http://www.naitoh.co.jp/msds/msds_041207.
html (accessed 3 December 2009)
546 Orbencarb, http://www.staehler.ch/pdf/smb/golaprex.d.
pdf (accessed 6 October 2009).
547 Pyributicarb, http://www.lookchem.com/PYRIBUTI-
CARB/ (accessed 15 November 2009).
548 Triallate, WHO/FAO Health and Safety Guide, no. 89,
1994.
549 Bilanafos, http://horizonscanning-defra.gov.uk/View-
Document_Image.aspx?Doc_ID165, pp134-135 (ac-
cessed 27 October 2009).
550 U.S. EPA, Registration Eligibility Decision for Fosa-
mine, 1995.
551 Fosamine, U.S. Federal Register 65 (2000) 57957
57961.
552 Glufosinate Ammonium, Pesticide Residues in Food-
1991. WHO/PCS 92.52 (1992) 209.
553 EU Commission: Gufosinate Ammonium, SANCO/
10453/2006-final, 2007.
554 EU Commission: Glyphosate, SANCO/6511/VI/99-
final, 2002.
555 Glyphosate, Pesticide Residues in Food-1986. FAO
Plant Protect. Prod. Paper 78/2 (1987) 63.
556 Novartis Nippon: Piperophos, J. Pesticide Sci. 16
(1991) 713.
557 Clethodim, Pesticide Residues in Food-1994. FAO Plant
Protect. Prod. Paper 127 (1995) 45.
558 Clethodim, U.S. Federal Register 63 (1998) 17101
17108.
559 Cycloxydim, Pesticide Residues in Food-1992. FAO
Plant Protect. Prod. Paper 126 (1993) 115.
560 Australian National Registration Authority for Agricul-
tural and Veterinary Chemicals: Profoxydim, Advice
Summary, 2007.
561 Sethoxydim, U.S. Federal Register 56 (1991)
11677.
562 Tepraloxydim, U.S. Federal Register 66 (2001)
4014140151.
563 Hexazinone U.S. EPA Pesticide Fact Sheet, no. 183,
1988.
564 A. Mine, O. Kirino, H. Matsumoto, Y. Takimoto, N.
Isobe: A new herbicide: Bromobutide, J. Pestic. Sci.
10 (1986) 520.
565 U.S. EPA, Diphenamid (Dymid, Emide) Herbicide Pro-
file, 2/85, 1985.
566 Flufenacet, U.S. Federal Register 68 (2003) 37749
37759.
567 U.S. EPA, Perfluidone (Destum) Herbicide Profile, 9/85,
1985.
568 U.S. EPA, Chloramben (Amiben) Herbicide Profile, 2/
85, 1985.
569 Chlorthal-methyl, U.S. Federal Register 69 (2004)
2538425390.
570 Pyrithiobac-sodium, U.S. EPA Pesticide Petition Filing,
7/01, 2001.
Vol. 39
571 Mesotrione, U.S. Federal Register 66 (2001) 33187
33195.
572 Tembotrione, U.S. EPA Human Health Risk Assess-
ment for Proposed Uses on Field Corn, Sweetcorn, and
Popcorn, 2007.
573 U.S. EPA, Environmental Fate and Ecological Risk
Assessment Registration of New Use for Flumiclorac-
pentyl, 2005.
574 U.S. EPA, Human Health Risk Assessment for Iodo-
methane, 2006.
575 U.S. EPA, Oxadiazon (Ronstar) Herbicide Profile, 2/85,
1985.
576 Isoxaflutole, U.S. Federal Register 63 (1998) 50773
50784.
577 BayerCropScience, MSDS for Benzofenap, 2007.
578 Benzofenap, http://www.foodmate.net/ (accessed 24
November 2009).
579 Pyraflufen-ethyl, U.S. Federal Register 68 (2003)
2304623056.
Weed Control, 2. Individual Herbicides 385
580 Pyrasulfotole, U.S. Federal Register 72 (2007)
4564345649.
581 Japanese Ministry for Agricultural, Fisheries and Forest,
Pyrazoxyfen, J. Pestic. Sci. 13 (1988) 167169.
582 Flufenpyr-ethyl, U.S. Federal Register 68 (2003)
3781337820, 5483454843.
583 Flufenpyr-ethyl, http://fsc.go.jp/senmon/nonyaku/kaku-
min1_dai11/nonyaku1_11 (accessed 30 October 2009).
584 U.S. EPA, Proposed Pesticide Tolerances for Diquat, 3/
96, 1996.
585 U.S. EPA, Paraquat Pesticide Petition Filing ,11/99,
1999.
586 U.S. EPA, Clomazone Summary Document Registration
Review: Initial Docket, 2007.
587 Indanofan, http://db.foodmate.net/pesticide/read_nyxz.
php?pid511 (accessed 30 November 2009).
588 Pyriftalid, http://www.fsc.go.jp/iinkai/i-dai181/dai181-
kai-siryon1-1.pdf (laccessed 26 November 2009).