New Potential Inhibitors of Pheromonal Attractionin the Oriental Fruit Moth, Cydia molesta

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Title:New Potential Inhibitors of Pheromonal Attractionin the Oriental Fruit Moth, Cydia molesta
Creators:
Hoskovec, Michal
Hovorka, Oldřich
Kalinová, Blanka
Koutek, Bohumír
Svatoš, Aleš
Šaman, David
Vlček, Kamil
Vrkoč, Jan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 7, pp. 1031-1044
Uncontrolled Keywords:Sex attractants, <i>Cydia molesta</i>, Pheromones, Electrophysiology, (<i>Z</i>)-Dodec-8-en-1-yl acetate, Oriental fruit moth, Sex pheromone analogues

Abstract

New analogues of (<i>Z</i>)-dodec-8-en-1-yl acetate (<i>Z</i>8-12:OAc, <strong>1</strong>), the main sex pheromone component of the Oriental fruit moth, <i>Cydia molesta</i>, were designed by formally transferring the terminal propyl group from the C-9 to the C-7 position to form vinyl-branched (<strong>2</strong>, <strong>3</strong>) or, after isomerization, ethylidene-branched (<strong>4</strong>) structures and by replacing the -CH=CH- grouping by the -S-CH<sub>2</sub>- moiety (<strong>5</strong>, <strong>6</strong>). 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 <strong>1</strong> following the order <strong>1</strong> &gt;&gt; <strong>6</strong> ≈ <strong>5</strong> &gt;&gt; <strong>2</strong> ≈ <strong>4</strong> ≈ <strong>3</strong>. 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 <strong>5</strong> and <strong>6</strong>. The results support the view that the inhibitory properties of the analogues should not be entirely associated with their pheromone-mimicking capabilities.

Title:New Potential Inhibitors of Pheromonal Attractionin the Oriental Fruit Moth, Cydia molesta
Creators:
Hoskovec, Michal
Hovorka, Oldřich
Kalinová, Blanka
Koutek, Bohumír
Svatoš, Aleš
Šaman, David
Vlček, Kamil
Vrkoč, Jan
Uncontrolled Keywords:Sex attractants, <i>Cydia molesta</i>, Pheromones, Electrophysiology, (<i>Z</i>)-Dodec-8-en-1-yl acetate, Oriental fruit moth, Sex pheromone analogues
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:7
Page Range:pp. 1031-1044
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19981031UNSPECIFIED
ID Code:1362
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Hoskovec, Michal; Hovorka, Oldřich; Kalinová, Blanka; Koutek, Bohumír; Svatoš, Aleš; Šaman, David; Vlček, Kamil; Vrkoč, Jan (1998) New Potential Inhibitors of Pheromonal Attractionin the Oriental Fruit Moth, Cydia molesta. Collection of Czechoslovak Chemical Communications, 63 (7). pp. 1031-1044. ISSN 0010-0765

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