Identification of a new lepidopteran sex pheromone in picogram quantities using an antennal biodetector: (8 E,10 Z)-tetradeca-8,10-dienal from Cameraria ohridella

Abstract

A major sex attractant released by the virgin female of the horse-chestnut leafminer Cameraria ohridella Deschka et Dimić (Lepidoptera: Gracillariidae) which devastates horse-chestnut trees in Europe, was identified in picogram quantities as (8 E,10 Z)-tetradeca-8,10-dienal without using spectral methods. The identification solely relied on gas chromatography with electroantennographic detection (GC-EAD), calculation of Kovats' indices of the active principle on different GC phases, and construction of antennal response spectra (EAG response profiles) to C 12 and C 14 saturated and unsaturated standards with different functional groups. The dienal was prepared by a stereospecific synthesis and shown to be highly active for conspecific males in pg amounts and fully comparable to the natural substance.