title: (Z,Z)-6,9-Heneicosadien-11-one: major sex pheromone component of painted apple moth, Teia anartoides.
abstract: (Z,Z)-6,9-Heneicosadien-11-one (Z6Z9-11-one-21Hy) was identified as the major sex pheromone component of the painted apple moth (PAM), Teia anartoides (Lepidoptera: Lymantriidae), on the basis of (1) comparative gas chromatographic-electroantennographic detection (GC-EAD) analyses, GC-mass spectrometry (MS), high-performance liquid chromatography (HPLC)-MS, and HPLC-UV/visible spectroscopy of pheromone gland extracts and authentic standards; (2) GC-EAD analyses of effluvia of calling females; and (3) wind tunnel and field trapping experiments with a synthetic standard. In field experiments in Australia, synthetic Z6Z9-11-one-21Hy as a single component attracted male moths. Wind tunnel experiments suggested that a 4-component blend consisting of Z6Z9-11-one-21Hy, (6Z,9R,10S)-cis-9,10-epoxy-heneicosene (Z6-9R10S-epo-21 Hy), (E,E)-7,9-heneicosadien-6, 11-dione (E7E9-6,11-dione-21Hy), and 6-hydroxy-(E,E)-7,9-heneicosadien-11-one (E7E9-6-ol-11-one-21Hy) (all present in pheromone gland extracts) might induce more males to orient toward, approach, and contact the source than did Z6Z9-11-one-21Hy as a single component. Additional experiments are needed to determine conclusively whether or not Z6-9R10S-epo-21Hy, E7E9-6,11-dione-21Hy, and E7E9-6-ol-11-one-21Hy might be minor sex pheromone components of PAM. Moreover, attractiveness of synthetic pheromone and virgin PAM females needs to be compared to determine whether synthetic pheromone could replace PAM females as trap baits in the program to monitor eradication of exotic PAM in New Zealand.
authors.affiliation: Department of Biological Sciences, Simon Fraser University, Burnaby British Columbia VSA 1S6, Canada. gries@sfu.ca
authors.forename: Regine
authors.initials: R
authors.lastname: Gries
authors.forename: Grigori
authors.initials: G
authors.lastname: Khaskin
authors.forename: John
authors.initials: J
authors.lastname: Clearwater
authors.forename: David
authors.initials: D
authors.lastname: Hasman
authors.forename: Paul W
authors.initials: PW
authors.lastname: Schaefer
authors.forename: Eugene
authors.initials: E
authors.lastname: Khaskin
authors.forename: Oleksandr
authors.initials: O
authors.lastname: Miroshnychenko
authors.forename: Gordon
authors.initials: G
authors.lastname: Hosking
authors.forename: Gerhard
authors.initials: G
authors.lastname: Gries
mesh_terms: D000818:Animals; D001522:Behavior, Animal / Q000502:physiology; D005233:Fatty Alcohols / Q000737:chemistry*; D005260:Female; D008297:Male; D015394:Molecular Structure; D009036:Moths / Q000737:chemistry / Q000502:physiology*; D012724:Sex Attractants / Q000737:chemistry* / Q000502:physiology
chemical_list: C477785:6,9-heneicosadien-11-one; D005233:Fatty Alcohols; D012724:Sex Attractants