Synthesis and Characterization of 3,13- and 2,13-Octadecadienyl Compounds for Identification of the Sex Pheromone Secreted by a Clearwing Moth, Nokona pernix

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著者

    • Naka Hideshi NAKA Hideshi
    • Entomology Group, Department of Biological Safety, National Institute for Agro-Environmental Sciences (NIAES)
    • YAMAMOTO Masanobu
    • Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture and Technology
    • ARITA Yutaka
    • Zoological Laboratory, Faculty of Agriculture, Meijo University
    • SUGIE Hajime
    • Entomology Group, Department of Biological Safety, National Institute for Agro-Environmental Sciences (NIAES)
    • TSUCHIDA Koji
    • Laboratory of Entomology, Faculty of Applied Biological Sciences, Gifu University
    • ANDO Tetsu
    • Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture and Technology

抄録

Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M−18]<SUP>+</SUP> at <I>m</I>⁄<I>z</I> 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, <I>Nokona pernix</I>, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, <I>viz.</I>, the (3<I>E</I>,13<I>Z</I>)- and (3<I>Z</I>,13<I>Z</I>)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted <I>N. pernix</I> males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.

収録刊行物

  • Bioscience, biotechnology, and biochemistry  

    Bioscience, biotechnology, and biochemistry 70(2), 508-516, 2006-02-23 

    Japan Society for Bioscience, Biotechnology, and Agrochemistry

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各種コード

  • NII論文ID(NAID)
    10018534609
  • NII書誌ID(NCID)
    AA10824164
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    09168451
  • NDL 記事登録ID
    7833612
  • NDL 雑誌分類
    ZR7(科学技術--農林水産--農産) // ZR2(科学技術--生物学--生化学) // ZP1(科学技術--化学・化学工業)
  • NDL 請求記号
    Z53-G223
  • データ提供元
    CJP書誌  CJP引用  NDL  J-STAGE 
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