Abstract
Enantiomer separation of (6Z,9Z)-cis-3,4-epoxynonadecadiene and (3Z,9Z)-cis-6,7-epoxynonadecadiene could be achieved using chiral high-resolution gas chromatography and a cyclodextrin-bond column. (3Z,9Z)-(6R,7S)-Epoxynonadecadiene was identified from ovipositor extracts of Colotois pennaria, while in Erannis defoliaria the 6S,7R-enantiomer was found. In field trapping tests pure synthetic enantiomers caught only conspecific males of these species. (3Z,6Z,9Z)-Nonadecatriene was found in both species, while the presence of (3Z,6Z,9Z)-hencicosatriene was indicated in C. pennaria only. A 10:10:3 blend of (3Z,9Z)-(6R,7S)-epoxynonadecadiene, (3Z,6Z,9Z)-heneicosatriene, and (3Z,6Z,9Z)-nonadecatriene was found to be optimal for catching C pennaria, while E. defoliaria males were optimally caught by a 1:1 mixture of (3Z,9Z)-(6S,7R)-epoxynonadecadiene and (3Z,6Z,9Z)-nonadecatriene. (6Z,9Z)-(3S,4R)-Epoxynonadecadiene was identified from ovipositor extracts of Agriopis (Erannis) aurantiaria. In field tests the pure enantiomer proved to be a highly specific sex attractant for both the late autumn/early winter flying A. aurantiaria and the late winter/early spring flying A. leucophearia. Males of Agriopis marginaria, which fly in late winter/early spring, were attracted to (3Z,9Z)-(6S,7R)-epoxynonadecadiene. The addition of (3Z,6Z,9Z)-nonadecatriene to the S,R-enantiomer increased captures. Optimal catches were recorded with a 10: 3 epoxide-hydrocarbon blend. Enantiomer specificity in all species was confirmed in EAG measurements.
