M. Hoskovec et al., NEW POTENTIAL INHIBITORS OF PHEROMONAL ATTRACTION IN THE ORIENTAL FRUIT MOTH, CYDIA-MOLESTA, Collection of Czechoslovak Chemical Communications, 63(7), 1998, pp. 1031-1044
New analogues of (Z)-dodec-8-en-1-yl acetate (Z8-12:OAc, 1), the main
sex pheromone component of the Oriental fruit moth, Cydia molesta, wer
e 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 isome
rization, ethylidene-branched 4) structures and by replacing the -CH=C
H- grouping by the -S-CH2- 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 low
er than that of 1 following the order 1 much greater than 6 approximat
e to 5 much greater than 2 approximate to 4 approximate to 3. The sing
le sensillum recording activities indicated that all the analogues sti
mulate 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 i
nhibitory effect (90%) was observed for the thia analogues 5 and 6. Th
e results support the view that the inhibitory properties of the analo
gues should not be entirely associated with their pheromone-mimicking
capabilities.