Canadian Forest Service Publications
(6Z,9Z-3R,4S)-Epoxy-heptadecadiene: Major sex pheromone component of teh Larch Looper, Semiothisa sexmaculata (Packard) (Lepidoptera: Geometridae) 1993. Gries, G.; Gries, R.; Underhill, E.W.; Humble, L.M. Journal of Chemical Ecology 19(4): 843-850.
Issued by: Pacific Forestry Centre
Catalog ID: 21527
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Gas chromatographic-electroantennographic analysis (GC-EAD) of female larch looper, Semiothisa sexmaculata (Packard), gland extracts revealed two EAD-active compounds. Retention index calculations, GC-mass spectroscopy in slected ion monitoring mode, and GC-EAD analysis of authentic standards identified the compounds as (3Z,6Z,9Z)-heptadecatriene (3Z,6Z,9Z-17:H) and (6Z,9Z)-cis-3,4-expoxy-heptadecadiene (6Z,9Z-cis-3,4-epoxy-17:H). Chirality determination of the monoepoxydiene in gland extracts was impeded by small quantities, but field experiments indicated that male S. sexmaculata were most strongly attracted to enantiomerically enriched 6Z,9Z-#R,4S-epoxy-17:H (69% ee), while male S. neptaria (Guenée) responded well to various blends of the R,S- and S,R-epoxide enantiomers. Binary combinations of the R,S-epoxide enantiomer with 3Z,6Z,9Z-17:H significantly inhibited response by male S. sexmaculata, but strongly enhanced attraction of sympatric male S. marmorata Ferguson. Enantiomerically enriched 6Z,9Z-3R,4S-epoxy-17:H can be used as a trap bait to monitor populations of the larch-defoliating S. sexmaculata. Whether 6Z,9Z-3R,4S-epoxy-17:H serves as single component sex pheromone in S. sexmaculata or small amounts of 6Z,9Z-3S,4R-epoxy-17:H synergize or suppress optimal attraction, will be tested as chirally pure monoepoxydienes become available.