(11Z,13E)-Hexadecadien-1-yl acetate: sex pheromone of the grass webworm Herpetogramma licarsisalis-identification, synthesis, and field bioassays.
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.
Gibb
Andrew R
AR
Horticulture and Food Research Institute of New Zealand Ltd., P.O. Box 51, Lincoln, New Zealand. agibb@hortresearch.co.nz
Suckling
D Max
DM
El-Sayed
Ashraf M
AM
Bohman
Björn
B
Unelius
C Rikard
CR
Dymock
Jennifer J
JJ
Larsen
Michelle L
ML
Willoughby
Bruce E
BE
D000818:Animals; D001681:Biological Assay; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D008297:Male; D009036:Moths / Q000502:physiology*; D012724:Sex Attractants / Q000096:biosynthesis / Q000737:chemistry / Q000378:metabolism*; D012726:Sexual Behavior, Animal
D012724:Sex Attractants