Gibb, Andrew R.Suckling, D. MaxEl-Sayed, Ashraf M.Bohman, BjornUnelius, C.R.Dymock, Jennifer J.Larsen, Michelle LWilloughby, Bruce E.2015-12-100098-0331http://hdl.handle.net/1885/63752The 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: sex pheromone; antagonism; attractant; bioassay; biochemical composition; caterpillar; inhibitor; moth; pheromone trap; sex pheromone; animal; article; bioassay; biosynthesis; chemistry; female; male; mass fragmentography; metabolism; moth; physiology; se (11Z,13E)-Hexadecadien-1-ol; (11Z,13E)-Hexadecadien-1-yl acetate; (Z)-11-Hexadecen-1-yl acetate; Behavioral antagonist; Crambidae; Grass webworm; Herpetogramma licarsisalis; MTAD200710.1007/s10886-007-9259-42015-12-10