Pheromonal Production of and Response to Optically Active Epoxydienes in Some Geometrid Moths (Lepidoptera: Geometridae)

In pheromone extracts of calling female Chiasma clathrata L. (Lepidoptera: Geometridae), a defoliator pest of alfalfa, (Z,Z,Z)-3,6,9-heptadecatriene and (Z,Z)-6,9-cis-3,4-epoxyheptadecadiene was identified. Chiral gas chromatography using a modified cyclodextrin and synthetic reference samples proved the natural epoxide to show (3R, 4S)-configuration. In field trapping tests, only the pure (3R, 4S)-enantiom er of the epoxide attracted males. The addition of the triene component was synergistic. Males of the sympatric species Tephrina arenacearia Hbn. (Lepidoptera: Geometridae) were caught only in traps with baits containing the (3S, 4R)-enantiomer [together with a previously described minor component, (Z,Z)-3,9-cis- 6,7-epoxyheptadecadiene]. In trapping tests conducted in a different biotope, Abraxas grossulariata L. (Lepidoptera: Geometridae) males were attracted by the (3S, 4R)-enantiomer, whereas the (3R, 4S)-enantiomer attracted a close relative, Abraxas sylvata Scop. (Lepidoptera: Geometridae). The present results suggest that one of the key mechanisms responsible for pheromone specificity among both the two alfalfa geometrids and the two A braxas species in their respective biotops, may be the use of different enantiomers of the same polyenederived epoxide as a sex pheromone component. It is probable that this discrimination mechanism is widespread among moth species utilizing epoxide pheromone components