(11Z,13E)-Hexadecadien-1-yl Acetate: Sex Pheromone of the Grass Webworm Herpetogramma licarsisalis--Identification, Synthesis, and Field Bioassays
2007
Gibb, Andrew R | Suckling, D Max | El-Sayed, Ashraf M | Bohman, Björn | Unelius, C Rikard | Dymock, Jennifer J | Larsen, Michelle L | Willoughby, Bruce E
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.
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