Abraxas grossulariata L. (Lepidoptera: Geometridae): identification of (3Z,6Z,9Z)-3,6,9-heptadecatriene and (6Z,9Z)-6,9-cis-3,4-epoxyheptadecadiene in the female sex pheromone

(3Z,6Z,9Z)-3,6,9-Heptadecatriene and (6Z,9Z)-6,9-cis-3,4-epoxyheptadecadiene have been identified in female sex pheromone gland extracts of Abraxas grossulariata L. (Lepidoptera: Geometridae). The compounds were detected by gas chromatography with electroantennographic detection (GC-EAD) and identified by GC-mass spectrometry (GC-MS). The amounts of hydrocarbon and epoxide were 0.13 and 0.42 ng/female, respectively. These identifications were confirmed by synthesis; the absolute configuration of the epoxide remains to be determined. Another isomeric epoxide, (3Z,6Z)-3,6-cis-9,10-epoxyheptadecadiene, was tentatively identified in small amounts (0.04 ng/female). Racemic (6Z,9Z)-6,9-cis-3,4-epoxyheptadecadiene elicited the largest electroantennogram response within a series of hertadecadiene and nonadecadiene monoepoxides and the corresponding trienic hydrocarbons and, in field tests, attracted male A. grossulariata into traps. Addition of 10% (3Z,6Z,9Z)-3,6,9-heptadecatriene to this epoxide enhanced attractiveness; addition of (3Z,6Z)-3,6-cis-9, 10-epoxyheptadecadiene had no effect at low proportions while higher proportions caused a reduction in the numbers of males caught