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. 1990 Jul;16(7):2153-66.
doi: 10.1007/BF01026927.

(3Z,6Z,9Z)-Nonadecatriene and enantiomers of (3Z,9Z)-cis-6,7-Epoxy-nonadecadiene as sex attractants for two geometrid and one noctuid moth species

J G Millar  1 , M Giblin, D Barton, E W Underhill
Affiliations

(3Z,6Z,9Z)-Nonadecatriene and enantiomers of (3Z,9Z)-cis-6,7-Epoxy-nonadecadiene as sex attractants for two geometrid and one noctuid moth species

J G Millar et al. J Chem Ecol. 1990 Jul.

Abstract

Sex attractants for the geometrid mothsEufidonia convergaria andCaripeta angustiorata, and the noctuid mothRivula propinqualis have been elucidated during field screening of a series of (3Z,6Z,9Z)-triene hydrocarbons (C17-22), and the racemic and enantiomerically enriched monoepoxydienes derived from those hydrocarbons. Biologically active compounds were identified by a combination of field testing of synthetic standards, electroantennography, and coupled gas chromatography-electroantennogram detection.E. convergaria males were optimally attracted by a 1∶1 blend of (3Z,9Z)-(6S,7R)-epoxy-nonadecadiene (3Z,9Z-6S,7R-epoxy-19∶H); other abbreviations follow the same system) with (3Z,6Z,9Z)-nonadecatriene (3Z,6Z,9Z-19∶H). The 6R,7S enantiomer of the epoxide had no apparent biological activity, either as an attractant or as a behavioral antagonist. Male moths also were attracted to blends of the C18 and C20 homologs of the triene and the epoxide. 3Z,6Z,9Z-19∶H and 3Z,6Z-cis-6,7-epoxy-19∶H were identified inE. convergaria female pheromone gland extracts. Males of the geometrid moth speciesC. angustiorata were attracted by a 1∶1 blend of 3Z,6Z,9Z-19∶H and enantiomerically enriched 3Z,9Z-6R,7S-epoxy-19∶H. Males of the noctuid mothR. propinqualis were attracted by an approximately 10∶1 blend of 3Z,6Z,9Z-19∶H and enantiomerically enriched 3Z,9Z-6S, 7R-epoxy-19∶H. The components were synergistic, with neither being attractive alone. The blend ratio was quite specific, as the attractiveness of blends decreased sharply on either side of the optimum ratio.

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