title: Enantiomers of (Z,Z)-6,9-heneicosadien-11-ol: sex pheromone components of Orgyia detrita.
abstract: (6Z,9Z,11S)-6,9-Heneicosadien-11-ol (Z6Z9-11S-ol-C21) and (6Z,9Z,11R)-6,9-heneicosadien-11-ol (Z6Z9-11R-ol-C21) were identified as major sex pheromone components of female tussock moths, Orgyia detrita Guérin-Méneville (Lepidoptera: Lymantriidae), on the basis of (1) analyses of pheromone gland extracts of female O. detrita by coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC mass spectrometry, and (2) field trapping experiments with synthetic standards. Z6Z9-11S-ol-C21 and Z6Z9-11R-ol-C21 in combination, but not singly, attracted significant numbers of male moths. Racemic Z6Z9-11-ol-C21 was more attractive than the 1:3.5 (R:S) blend ratio found in pheromone gland extracts from female moths. Lower and higher homologues of Z6Z9-11-ol-C21 were also detected in GC-EAD recordings of pheromone extracts, and the racemic compounds enhanced attractiveness of Z6Z9-11-ol-C21 in field experiments. Because of trace amounts of these homologues in extracts, their enantiomeric composition could not be determined. This is the first report of secondary alcohols as pheromone components in the ditrysian (advanced) Lepidoptera.
authors.affiliation: Department of Biological Sciences, Simon Fraser University, Burnaby, British Columbia, Canada, V5A 1S6.
authors.forename: Regine
authors.initials: R
authors.lastname: Gries
authors.forename: Grigori
authors.initials: G
authors.lastname: Khaskin
authors.forename: Eugene
authors.initials: E
authors.lastname: Khaskin
authors.forename: John L
authors.initials: JL
authors.lastname: Foltz
authors.forename: Paul W
authors.initials: PW
authors.lastname: Schaefer
authors.forename: Gerhard
authors.initials: G
authors.lastname: Gries
mesh_terms: D000466:Alkadienes / Q000737:chemistry* / Q000494:pharmacology; D000818:Animals; D005260:Female; D008297:Male; D009036:Moths / Q000737:chemistry / Q000502:physiology*; D009068:Movement; D012724:Sex Attractants / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: C482761:(Z,Z)-6,9-heneicosadien-11-ol; D000466:Alkadienes; D012724:Sex Attractants