Species discrimination in five species of winter-flying geometrids (Lepidoptera) based on chirality of semiochemicals and flight season

G. Szöcs, M. Tóth, W. Francke, F. Schmidt, P. Philipp, W. A. König, K. Mori, B. S. Hansson, C. Löfstedt

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Abstract

Enantiomer separation of (6 Z,9 Z)-cis-3,4-epoxynonadecadiene and (3 Z,9 Z)-cis-6,7-epoxynonadecadiene could be achieved using chiral high-resolution gas chromatography and a cyclodextrin-bond column. (3 Z,9 Z)-(6 R,7 S)-Epoxynonadecadiene was identified from ovipositor extracts of Colotois pen-Naria, while in Erannis defoliaria the 6 S,7 R-enantiomer was found. In field trapping tests pure synthetic enantiomers caught only conspecific males of these species. (3 Z,6 Z,9 Z)-Nonadecatriene was found in both species, while the presence of (3 Z,6 Z,9 Z)-heneicosatriene was indicated in C. Pennaria only. A 10:10:3 blend of (3 Z,9 Z)-(6 R,7 S)-epoxynonadecadiene, (3 Z,6 Z,9 Z)-heneicosatriene, and (3 Z,6 Z,9 Z)-nonadecatriene was found to be optimal for catching C. Pennaria, while E. Defoliaria males were optimally caught by a 1:1 mixture of (3 Z,9 Z)-(6 S,7 R)-epoxynonadecadiene and (3 Z,6 Z,9 Z)-nona-decatriene. (6 Z,9 Z)-(3 S,4 R)-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 (3 Z,9 Z)-(6 S,7 R)-epoxynonadecadiene. The addition of (3 Z,6 Z,9 Z)-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.

Original languageEnglish
Pages (from-to)2721-2735
Number of pages15
JournalJournal of Chemical Ecology
Volume19
Issue number11
DOIs
Publication statusPublished - Nov 1 1993

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Keywords

  • (3 Z,9 Z)-(6 R,7 S)-epoxynonadecadiene
  • (3 Z,9 Z)-(6 S,7 R)-epoxynonadecadiene
  • (6 Z,9 Z)-(3 S,4 R)-epoxynonadecadiene
  • A. leucophearia
  • A. marginaria
  • Agriopis aurantiaria
  • Chirality
  • Colotois pennaria
  • Erannis defoliaria
  • Geometridae
  • Lepidoptera
  • electroantennogram
  • enantiomers
  • field trapping
  • sex pheromones

ASJC Scopus subject areas

  • Ecology, Evolution, Behavior and Systematics
  • Biochemistry

Cite this

Szöcs, G., Tóth, M., Francke, W., Schmidt, F., Philipp, P., König, W. A., Mori, K., Hansson, B. S., & Löfstedt, C. (1993). Species discrimination in five species of winter-flying geometrids (Lepidoptera) based on chirality of semiochemicals and flight season. Journal of Chemical Ecology, 19(11), 2721-2735. https://doi.org/10.1007/BF00980703