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Krista Ryall Peter J. Silk Junping Wu Peter Mayo Matthew A. Lemay David MaGee 《Die Naturwissenschaften》2010,97(8):717-724
The elm spanworm, Ennomos subsignaria (Hübner), occurs throughout Canada and the eastern United States and can be a destructive forest pest on a wide range of
deciduous trees. Gas chromatography/mass spectrometry (GC/MS) and coupled gas chromatographic–electroantennographic detection
(GC/EAD) analysis of pheromone gland extracts, in combination with chemical synthesis and field trapping studies have identified
(2S, 3R)-2-((Z)-oct-2′-enyl)-3-nonyl oxirane (hereafter Z6-9S, 10R-epoxy-19:H) as the female-produced sex pheromone. Significantly more male moths were captured between 1–100 μg loadings of
this compound on red rubber septa in sticky traps compared to blank (unbaited) traps; catches then declined at higher dosages
(500–1000 μg). The other isomeric enantiomer, (2R, 3S)-2-[(Z)-oct-2′-enyl]-3-nonyl oxirane (Z6-9R, 10S-epoxy-19:H), at a 10-μg dosage did not elicit trap capture. The likely precursor to the active epoxide, (Z, Z)-6, 9-nonadecadiene ((Z, Z)-6, 9-19:H), identified in virgin female sex pheromone glands, did not elicit trap capture either, and inhibited trap capture
when combined with the active epoxide. Racemic 2-((Z)-oct-2′-enyl)-3-nonyl oxirane showed no significant difference in trap
capture compared with Z6-9S, 10R-epoxy-19:H, indicating that the opposite enantiomer was not antagonistic. The addition of the EAD-active diene epoxide enantiomers
(2S, 3R)-2-[(Z, Z)-octa-2′, 5′-dienyl]-3-nonyl oxirane or (2R, 3S)-2-[(Z, Z)-octa-2′, 5′-dienyl]-3-nonyl oxirane in admixture with Z6-9S, 10R-epoxy-19:H (at 10% of the latter) did not enhance or decrease trap capture compared to Z6-9S, 10R-epoxy-19:H oxirane alone, so they are not likely pheromone components. This pheromone, impregnated in rubber septa at less
than 100-μg dosage, can now be used as a trap bait to develop detection and monitoring strategies for this insect. 相似文献