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3Z, 13Z-Octadecadienyl acetate: Sex pheromone of the apple clearwing moth in British Columbia

Judd, G.J.R., Gries, R., Aurelian, V.M., Gries, G. (2011). 3Z, 13Z-Octadecadienyl acetate: Sex pheromone of the apple clearwing moth in British Columbia, 143(3), 236-244.


The apple clearwing moth, Synanthedon myopaeformis (Borkhausen) (Lepidoptera: Sesiidae), is a European species discovered in Cawston, British Columbia, Canada, in 2005. Using coupled gas chromatographic electroantennographic detection analyses we identified candidate sex pheromone components in pheromone gland extracts and effluvia from calling females. Analysis of gland extracts using four gas-chromatography (GC) columns (DB-5, DB-17, DB-23, and DB-210) showed three components (A, B, and C) that consistently elicited strong responses from male antennae. Based on previous work, the most antennally stimulatory component, B, was hypothesized to be (3Z,13Z)-octadecadienyl acetate ((3Z,13Z)-18:OAc). Its retention time on the four GC columns and its mass spectrum in a concentrated extract matched those of an authentic standard, thus confirming structural assignment. Components A and C were below the detection threshold of the mass spectrometer, but their retention times on the four GC columns matched those of authentic standards of (3Z,13Z)-octadecadienol ((3Z,13Z)18:OH) and (2E,13Z)-octadecadienyl acetate ((2E,13Z)-18:OAc), respectively. Synthetic (3Z,13Z)-18:OAc, (3Z,13Z)-18:OH, and (2E,13Z)-18:OAc all elicited strong responses from male antennae, further supporting structural assignments of these three components. Of these antennally active compounds, only (3Z,13Z)-18:OAc and (3Z,13Z)-18:OH were detected in effluvia from calling female moths. In field trapping tests in Cawston, (3Z,13Z)-18:OAc alone was as attractive as, or more attractive than, binary or ternary blends containing this component. (2E,13Z)-18:OAc was behaviourally inactive alone or in combination with (3Z,13Z)-18:OAc, whereas 5% (3Z,13Z)-18:OH appeared antagonistic. Our analysis confirms that (3Z,13Z)-18:OAc is the major pheromone component in S. myopaeformis, and it alone is sufficiently attractive for use in detection surveys and development of pheromone-based controls for this introduced pest in Canada. © 2011 Entomological Society of Canada.

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