(11Z,13E)-Hexadecadien-1-yl Acetate: Sex Pheromone of the Grass Webworm Herpetogramma licarsisalis- Identification,Synthesis,and Field Bioassays

摘要

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 micro-chemical 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 pheromonc 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,Zll-16:Ac had no effect on the attractiveness of lures.