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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概要
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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]+ at m⁄z 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, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-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 N. pernix 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.
- 2006-02-23
著者
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Naka Hideshi
National Institute For Agro-environmental Sciences (niaes):(present Office)laboratory Of Applied Ent
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Ando T
Department Of Applied Biological Science Faculty Of Agriculture Tokyo University Of Agriculture And
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Ando Tomoaki
Division Of Bioscience And Biotechnology Department Of Ecological Engineering Toyohashi University O
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ANDO Tetsu
Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture
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Yamamoto Masanobu
Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Tec
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TSUCHIDA Koji
Laboratory of Entomology, Faculty of Agriculture, Gifu University
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ARITA Yutaka
Zoological Laboratory, Faculty of Agriculture, Meijo University
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HORIE Yoshiteru
Zoological Laboratory, Faculty of Agriculture, Meijo University
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NAKA Hideshi
Entomology Group, Department of Biological Safety, National Institute for Agro-Environmental Science
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NAKAZAWA Tomotake
Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture
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SUGIE Mieko
Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture
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WAKASUGI Ryohei
Zoological Laboratory, Faculty of Agriculture, Meijo University
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SUGIE Hajime
Entomology Group, Department of Biological Safety, National Institute for Agro-Environmental Science
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Yamamoto Masanobu
Graduate School Of Bio-applications And Systems Engineering (base) Tokyo University Of Agriculture A
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Ando T
Graduate School Of Bio-applications And Systems Engineering (base) Tokyo University Of Agriculture A
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Ando Tetsu
Graduate School Of Bio-applications And Systems Engineering (base) Tokyo University Of Agriculture A
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Sugie Mieko
Graduate School Of Bio-applications And Systems Engineering (base) Tokyo University Of Agriculture A
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Naka Hiromi
National Institute For Agro-environmental Sciences (niaes):(present Office)laboratory Of Applied Ent
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Sugie Hajime
Entomology Group Department Of Biological Safety National Institute For Agro-environmental Sciences
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Arita Yutaka
Zoological Lab. Fac. Of Agriculture Meijo Univ.
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Tsuchida K
Division Of Radiological Protection And Biology National Institute Of Infectious Diseases
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Wakasugi Ryohei
Zoological Laboratory Faculty Of Agriculture Meijo University
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Horie Yoshiteru
Zoological Laboratory Faculty Of Agriculture Meijo University
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Tsuchida Koji
Laboratory Of Ecological Entomology Faculty Of Applied Biological Sciences Gifu University
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Ando Tetsu
Graduate School Of Bio-applications And Systems Engineering Tokyo University Of Agriculture And Tech
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Nakazawa Tomotake
Graduate School Of Bio-applications And Systems Engineering (base) Tokyo University Of Agriculture A
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