ChemInform Abstract: New Potential Inhibitors of Pheromonal Attraction in the Oriental Fruit Moth, Cydia molesta

Autor: Bohumír Koutek, Kamil Vlcek, Aleš Svatoš, Jan Vrkoč, David Šaman, Blanka Kalinova, Oldrich Hovorka, Michal Hoskovec
Rok vydání: 2010
Předmět:
Zdroj: ChemInform. 30
ISSN: 1522-2667
0931-7597
DOI: 10.1002/chin.199907270
Popis: New analogues of ( Z )-dodec-8-en-1-yl acetate ( Z 8-12:OAc, 1 ), the main sex pheromone component of the Oriental fruit moth, Cydia molesta , were designed by formally transferring the terminal propyl group from the C-9 to the C-7 position to form vinyl-branched ( 2 , 3 ) or, after isomerization, ethylidene-branched ( 4 ) structures and by replacing the -CH=CH- grouping by the -S-CH 2 - moiety ( 5 , 6 ). Their biological activities were studied both electrophysiologically and behaviourally (laboratory mating and wind tunnel experiments). All the structural modifications resulted in analogues whose electroantennographic activities were lower than that of 1 following the order 1 >> 6 ≈ 5 >> 2 ≈ 4 ≈ 3 . The single sensillum recording activities indicated that all the analogues stimulate the same Z8-12:OAc receptor neurone. In behavioural experiments, the analogues were generally found to reduce the ability of males to find a pheromone source, however, to different degrees. The highest inhibitory effect (90%) was observed for the thia analogues 5 and 6 . The results support the view that the inhibitory properties of the analogues should not be entirely associated with their pheromone-mimicking capabilities.
Databáze: OpenAIRE
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