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J Chem Ecol

Title:		"(11Z,13E)-Hexadecadien-1-yl acetate: sex pheromone of the grass webworm Herpetogramma licarsisalis-identification, synthesis, and field bioassays"
Author(s):		Gibb AR; Suckling DM; El-Sayed AM; Bohman B; Unelius CR; Dymock JJ; Larsen ML; Willoughby BE;
Address:		"Horticulture and Food Research Institute of New Zealand Ltd., P.O. Box 51, Lincoln, New Zealand. agibb@hortresearch.co.nz"
Journal Title:		J Chem Ecol
Year:		2007
Volume:		20070302
Issue:		4
Page Number:		839 - 847
DOI:		10.1007/s10886-007-9259-4
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"The grass webworm Herpetogramma licarsisalis (Lepidoptera: Crambidae), which has recently established in pasture in Northland, New Zealand, is an important pest of many tropical and subtropical grasses. Two pheromone components, (Z)-11-hexadecen-1-yl acetate (Z11-16:Ac) and (11Z,13E)-hexadecadien-1-yl acetate (Z11,E13-16:Ac), were identified in pheromone gland extracts of female moths by gas chromatography (GC), GC-electroantennographic detection, and GC-mass spectrometry in conjunction with microchemical tests (dimethyldisulfide and 4-methyl-1,2,4-triazoline-3,5-dione derivatizations). Z11,E13-16:Ac and its geometric isomer (11E,13Z)-hexadecadien-1-yl acetate (E11,Z13-16:Ac) were synthesized via stereoselective Wittig reactions, and the identity of the diene present in the pheromone glands was confirmed to be Z11,E13-16:Ac. Field bioassays at Indooroopilly in Brisbane, Australia, established that Z11,E13-16:Ac was necessary and sufficient for attraction of male grass webworm moths and that the corresponding alcohol, (11Z,13E)-hexadecadien-1-ol (Z11,E13-16:OH), had a strong inhibitory effect on trap catches at the ratios tested. When mixed with Z11,E13-16:Ac in various ratios, Z11-16:Ac had no effect on the attractiveness of lures"
Keywords:		"Animals Biological Assay Female Gas Chromatography-Mass Spectrometry Male Moths/*physiology Sex Attractants/biosynthesis/chemistry/*metabolism Sexual Behavior, Animal;"
Notes:		"MedlineGibb, Andrew R Suckling, D Max El-Sayed, Ashraf M Bohman, Bjorn Unelius, C Rikard Dymock, Jennifer J Larsen, Michelle L Willoughby, Bruce E eng Research Support, Non-U.S. Gov't 2007/03/06 J Chem Ecol. 2007 Apr; 33(4):839-47. doi: 10.1007/s10886-007-9259-4. Epub 2007 Mar 2"