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

• 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.

Subject headings

NATURVETENSKAP  -- Biologi -- Ekologi (hsv//swe)

NATURAL SCIENCES  -- Biological Sciences -- Ecology (hsv//eng)

Keyword

(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

electroantennogram

enantiomers

Erannis defoliaria

field trapping

Geometridae

Lepidoptera

sex pheromones

Publication and Content Type

art (subject category)

ref (subject category)