Synthesis and characterization of 3,13- and 2,13-octadecadienyl compounds for identification of the sex pheromone secreted by a clearwing moth, Nokona pernix.
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.
Naka
Hideshi
H
Entomology Group, Department of Biological Safety, National Institute for Agro-Environmental Sciences (NIAES), Ibaraki, Japan.
Nakazawa
Tomotake
T
Sugie
Mieko
M
Yamamoto
Masanobu
M
Horie
Yoshiteru
Y
Wakasugi
Ryohei
R
Arita
Yutaka
Y
Sugie
Hajime
H
Tsuchida
Koji
K
Ando
Tetsu
T
D000818:Animals; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D015394:Molecular Structure; D009036:Moths / Q000737:chemistry / Q000378:metabolism*; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*
D012724:Sex Attractants