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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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.
- Agricultural and Biological Chemistry
Agricultural and Biological Chemistry 70(2), 508-516, 2006-02-23
Japan Society for Bioscience, Biotechnology, and Agrochemistry