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

Andrew R. Gibb, D. Max Suckling, Ashraf M. El-Sayed, Björn Bohman, C. Rikard Unelius, Jennifer J. Dymock, Michelle L. Larsen, Bruce E. Willoughby

Research output: Contribution to journalArticle

5 Citations (Scopus)

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.
Original languageEnglish
JournalJournal of Chemical Ecology
Volume33
Issue number4
DOIs
Publication statusPublished - 2007
Externally publishedYes

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Herpetogramma licarsisalis
Herpetogramma
Sex Attractants
Bioassay
sex pheromone
Pheromones
sex pheromones
Poaceae
pheromone
Biological Assay
Gas chromatography
pheromone glands
bioassay
acetate
gas chromatography
Acetates
Moths
bioassays
acetates
grass

Cite this

Gibb, Andrew R. ; Suckling, D. Max ; El-Sayed, Ashraf M. ; Bohman, Björn ; Unelius, C. Rikard ; Dymock, Jennifer J. ; Larsen, Michelle L. ; Willoughby, Bruce E. / (11Z,13E)-Hexadecadien-1-yl Acetate: Sex Pheromone of the Grass Webworm Herpetogramma licarsisalis—Identification, Synthesis, and Field Bioassays. In: Journal of Chemical Ecology. 2007 ; Vol. 33, No. 4.
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title = "(11Z,13E)-Hexadecadien-1-yl Acetate: Sex Pheromone of the Grass Webworm Herpetogramma licarsisalis—Identification, Synthesis, and Field Bioassays",
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.",
author = "Gibb, {Andrew R.} and Suckling, {D. Max} and El-Sayed, {Ashraf M.} and Bj{\"o}rn Bohman and Unelius, {C. Rikard} and Dymock, {Jennifer J.} and Larsen, {Michelle L.} and Willoughby, {Bruce E.}",
year = "2007",
doi = "10.1007/s10886-007-9259-4",
language = "English",
volume = "33",
journal = "Journal of Chemical Ecology",
issn = "0098-0331",
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(11Z,13E)-Hexadecadien-1-yl Acetate: Sex Pheromone of the Grass Webworm Herpetogramma licarsisalis—Identification, Synthesis, and Field Bioassays. / Gibb, Andrew R.; Suckling, D. Max; El-Sayed, Ashraf M.; Bohman, Björn; Unelius, C. Rikard; Dymock, Jennifer J.; Larsen, Michelle L.; Willoughby, Bruce E.

In: Journal of Chemical Ecology, Vol. 33, No. 4, 2007.

Research output: Contribution to journalArticle

TY - JOUR

T1 - (11Z,13E)-Hexadecadien-1-yl Acetate: Sex Pheromone of the Grass Webworm Herpetogramma licarsisalis—Identification, Synthesis, and Field Bioassays

AU - Gibb, Andrew R.

AU - Suckling, D. Max

AU - El-Sayed, Ashraf M.

AU - Bohman, Björn

AU - Unelius, C. Rikard

AU - Dymock, Jennifer J.

AU - Larsen, Michelle L.

AU - Willoughby, Bruce E.

PY - 2007

Y1 - 2007

N2 - 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.

AB - 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.

U2 - 10.1007/s10886-007-9259-4

DO - 10.1007/s10886-007-9259-4

M3 - Article

VL - 33

JO - Journal of Chemical Ecology

JF - Journal of Chemical Ecology

SN - 0098-0331

IS - 4

ER -