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Semiochemicals are small organic compounds that transmit chemical messages. They are
used by insects for intra- and interspecies communication. Insects detect semiochemicals
directly from the air with olfactory receptors. In most insects, the receptors are located in
sensilla hairs on the antennae. The term "semiochemical" has been in use since 1971. It is
derived from the Greek word "semeon," which means "sign" or "signal."
Semiochemicals were already being studied in the 1880s. Although their chemistry was
not yet understood at that time, people already knew about using female insects to lure
males into traps. Semiochemical research in its present form has been conducted since the
1950s, when the first pheromones were isolated and identified. From the 1950s up until
today, more than 3,000 semiochemicals connected to the chemical communication of
insects have been identified. Current research on semiochemicals involves continued
molecular mapping, synthesis and studies of biosynthesis. Another research area that has
gained importance over the years has been an effort to understand the neurophysiological
sensory functions of insects and how hormonal regulation in insects affects pheromone
biosynthesis and release. The practical goal of semiochemical research is to develop means
and methods of exterminating and controlling insect pests. Semiochemical research is
placed in Pasteur's Quadrant of the Stokes model. It is based on pure research in chemistry,
but the final goal is still to develop solutions for practical problems through applied
research.
The chemical analysis of semiochemicals should consider both effect and structure (see
Figure 1). In terms of effect, semiochemicals can be classified as pheromones or
allelochemicals based on how they are used and who benefits. In terms of structure,
semiochemicals can be divided into twenty-four classes according to functional groups.
Pheromones
Pheromones are compounds used by insects for intraspecies communication. The term
"pheromone" is derived from the Greek words "pherein" (to carry) and "horman" (to
excite/stimulate). The term was introduced in 1959 by Karlsson and Butenandt and by
Karlsson and Lscher simultaneously. The difference between pheromones and hormones
is that hormones are produced in an insect's endocrine glands. They have an effect on the
insect that produces them, whereas pheromones affect other individuals instead. Based on
their effect, pheromones can be divided into at least the following categories:
Sex pheromones (Figure 2): compounds that help individuals of the opposite sex to
find each other.
Trail pheromones: among social insects, compounds used by workers to mark the
way to a food source, for example.
The effect of a semiochemical is influenced by its molecular weight. Most of the alarm
pheromones, for example, have a molecular weight below 200 g/mol. Once the danger has
passed, they evaporate. Trail pheromones, on the other hand, have higher molecular
weights. They are not supposed to evaporate immediately.
Allelochemicals
The allelochemicals are classified as allomones, kairomones or synomones. Allomones are
a class of compounds that benefit the producer, but not the receiver. Allomones are often
found in nature as part of a chemical defense, such as toxic insect secretions. Predators
also use allomones to lure prey.
Kairomones are a class of compounds that are advantageous for the receiver. The term
"kairomone" is derived from the Greek word "kairos," which means "opportunistic"
(Nordlund et al. 1981, 18). Kairomones benefit many predators and bugs, for example, by
guiding them to prey or potential host insects.
Synomones (from the Greek "syn" for "with" or "together") are compounds that are
beneficial to both the receiver and the sender.
Functional
group
Category
Esters
1. Carboxylic esters
2. Acetate esters
3. Cyclic esters
430
340
75
- Basic structure
- Substituents
- Characteristic
features
- Carbon chain (C2C41)
- Double bonds
- Isomerism
- Ring structures (cyclic
esters)
- Methyl and propyl groups
O
OR
580
alkaani
alkane
5. Ketones
alkeeni
alkene
alkyyni
alkyne
400
O
R
Alcohols
6. Primary alcohols
7. Secondary
alcohols
8. Tertiary alcohols
210
150
30
9. Amines
300
10. Aldehydes
260
OH
H
OH
R H
OH
R R
prim.
Primary
sek.
Secondary
tert.
Tertiary
H H
R R
R
prim.
sek.
tert.
Primary Secondary Tertiary
O
R
Table 1, continued
11. Carboxylic acids
OH
12. Epoxides
210
100
R
R
OH
13. Phenols
55
e.g.
14. Spiroacetals
50
O
R
15. Diols
40
OH
HO
e.g.
16. Quinones
40
O
e.g.
17. Dioxy
30
R
18. Sulfur
compounds
19. Ethers
O
O
30
- Structure includes S
bond
20
20. Furans
20
21. Polyhydroxy
20
22. Pyrans
15
e.g.
23. Triols
OH
HO
OH
e.g.
24. Oximes
Total
>3200
HO
Esters
Esters are carboxylic acid derivatives with a COOR functional group. They are the largest
category of semiochemicals in the database, and are widely distributed in nature. Esters
have a pleasant odor and taste. They are characterized by having a high boiling point,
relative to molecular size, due to the oxygen atoms in their structure.
Semiochemicals include three types of esters: carboxylic esters, acetate esters and cyclic
esters. The category also includes nitrogen-containing compounds such as ammonium
acetate (C2H5NO2). Stereoisomerism occurs among the semiochemical esters. The most
common substituents in the category are methyl and propyl groups.
Hydrocarbons
The basic structure of this category is a simple, straight carbon chain (C2C45). The
chemical diversity of the category arises from differences in degrees of saturation,
isomerism, cyclic structure and aromaticity. The most frequently occurring side chains in
this category are methyl and propyl groups.
Semiochemical applications