Journal of Chemical Ecology

, Volume 26, Issue 11, pp 2579–2590 | Cite as

Identification of Chiral Sex Pheromone Secreted by Giant Geometrid Moth, Biston robustum Butler

  • Masanobu Yamamoto
  • Masaaki Kiso
  • Hiroyuki Yamazawa
  • Jun Takeuchi
  • Tetsu Ando


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.

Female sex pheromones Lepidoptera Geometridae Ennominae epoxynonadecene epoxynonadecadiene chiral epoxide chiral HPLC dimethyl disulfide adduct 


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Copyright information

© Plenum Publishing Corporation 2000

Authors and Affiliations

  • Masanobu Yamamoto
    • 1
  • Masaaki Kiso
    • 2
  • Hiroyuki Yamazawa
    • 1
  • Jun Takeuchi
    • 3
  • Tetsu Ando
    • 1
  1. 1.Graduate School of Bio-Applications and Systems EngineeringTokyo University of Agriculture and Technology, KoganeiTokyoJapan
  2. 2.Agricultural Technology Center, Hachijo-jimaTokyoJapan
  3. 3.Agricultural Technology Center, Hachijo-jimaTokyoJapan

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