Abstract
Biston robustum Butler, a polyphagous defoliator, multiplied on Hachijo-jima Island in 1997–1998. Based on GC-MS data of authentic standards, an analysis of a pheromone gland extract of the females indicated that it included (Z,Z)-6,9–nonadecadiene (I), (Z,Z,Z)-3,6,9–nonadecatriene (II), cis-(Z)-6,7–epoxy-9–nonadecene (III), and cis-(Z,Z)-6,7–epoxy-3,9–nonadecadiene (IV) in a ratio of 13 : 2 : 70 : 15. The structure of III was confirmed by a GC-MS analysis of another extract treated with dimethyl disulfide (DMDS). This epoxymonoene was successfully converted into the corresponding DMDS adduct that showed diagnostic ions fragmented at an epoxy ring and at thiomethoxy groups reflecting the position of an original double bond. Furthermore, the 6S,7R configuration was assigned for the epoxy ring of III by chiral HPLC analysis. Field examination of synthetic lures revealed that the two epoxy compounds (III and IV) with the 6S,7R configuration were essential components and that the two unsaturated hydrocarbons (I and II) showed a synergistic effect on male attraction.
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Yamamoto, M., Kiso, M., Yamazawa, H. et al. Identification of Chiral Sex Pheromone Secreted by Giant Geometrid Moth, Biston robustum Butler. J Chem Ecol 26, 2579–2590 (2000). https://doi.org/10.1023/A:1005540913934
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DOI: https://doi.org/10.1023/A:1005540913934