Insect Chemical Communication from the Viewpoint of the Organic Chemist
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague
The multiscience complexity of the research in the field of the insect chemical communication is demonstrated on the project Biorational Pesticides Based on Pheromone Analogues. The project dealt with the design, synthesis and structure - biological activity studies of sex pheromone analogues of some important insect pests, such as the oriental fruit moth (Cydia molesta). Ten new analogues of (Z)-dec-8-en-1-yl acetate (I) with the modified acetate group (II -V) or alkene moiety (VI- XI) were tested for their biological activity by electroantennography (EAG), electrosensillography (ESG), short-range sexual stimulation and activation in the flight tunnel. All the structure modifications resulted in compounds whose electrophysiological activities were lower than that of I following the order I > II > VII > IV > VIII = IV = VI >> III >>> V = IX = X = XI. In behaviour experiments, some of the synthesised compounds were found to generally reduce the ability of males to find a pheromone source. The highest inhibitory effect was observed for chloroformate II, the four-membered lactone III and the thia analogues VI and VII. The results support the view that inhibitory properties of the analogues should not be entirely associated with their pheromone-mimicking capabilities.
Full text (PDF)