Chiral Lepidopteran Sex Attractants: Blends of Optically Active C 20 and C 21 Diene Epoxides as Sex Attractants for Geometrid and Noctuid Moths (Lepidoptera)

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Abstract
Sex attractants and behavioral antagonists comprising C 20 and C 21 triene hydrocarbons and chiral epoxydienes are reported for male moths of two noctuid and six geometrid species. Moths of the noctuid Idia americalis (Guenée) were attracted to lures containing a 1:1 mixture of 3 Z ,9 Z -6 S ,7 R -epoxy-eicosadiene (3 Z ,9 Z -6 S ,7 R -epoxy-20:H) and 3 Z ,9 Z -6 S ,7 R -epoxy-21:H. Moths of the noctuid species Bleptina caradrinalis (Guenée) were specifically attracted to a blend consisting of a 1:1 mixture of the enantiomers of 3 Z ,9 Z - cis -6,7-epoxy-20:H and to a 4:1 mixture of the enantiomers of 3 Z ,9 Z - cis -6,7-epoxy-21:H. The following geometrid moth species were also caught (optimum lure components in parentheses): Plagodis alcoolaria (Guenée) (3 Z ,9 Z -6 R ,7 S -epoxy-20:H + 3 Z ,6 Z ,9 Z -20:H), Xanthorhoe munitata Hübner (3 Z ,9 Z -6 S ,7 R -epoxy-21:H + 3 Z ,6 Z ,9 Z -21:H), X. abrasaria aquilonaria (Herrich-Schäffer) (3 Z ,9 Z -6 S ,7 R -epoxy-21:H + 3 Z ,6 Z -9 S ,10 R -epoxy-21:H), X. ferrugata (Clerck) (3 Z ,9 Z -6 S ,7 R -epoxy-21:H), Mesoleuca ruficillata (Guenée) (3 Z ,6 Z ,9 Z -20:H or 3 Z ,6 Z ,9 Z -21:H or both), and Anticlea vasiliata (Guenée) (3 Z ,6 Z ,9 Z -21:H). Chiral and achiral attractants for one species often acted as antagonists for closely related or sympatrie species, indicating how discrete chemical communication channels may be maintained.

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