NEW MIMICS OF LEPIDOPTERAN ACETATE PHEROMONES

Michal HOSKOVEC, Oldrich HOVORKA, Blanka KALINOVÁ Bohumír KOUTEK, Ludvik STREINZ, Ales SVATOS, David SAMAN and Jan VRKOC
Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences,
166 10 Prague 6, Czech Republic


Antenal olfactory (EAG, ESG) as well as short-range and flight tunnel behavioral tests were carried out on the response of oriental fnuit moth, Cydia molesta, and European com borer, Ostrinia nubilalis, to their sexual pheromone analogs. The analogs were designed by i) replacing the double bond in the pheromone chain with isosteric -SCH2 moiety, ii) formally transfening the terminal n-alkyl group to the inner position to form branched structures, and, iii) by modifying the acetate functionality.

The ESG data indicate, in general, reduced receptor interactions of all analogs investigated when compared to parent molecule. While the sulfur compounds and chloroformiates were the most active, the branched analogs, however, did not elicit any receptor potential. In behavioral tests, the thia-analogs, chloroformates and lactones (n=1) were found to be effective mating inhibitors.


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