(Z,Z)-4,7-tridecadien-(S)-2-yl acetate: sex pheromone of Douglas-fir cone gall midge, Contarinia oregonensis.
Our objectives were to identify and field test the sex pheromone of female Douglas-fir cone gall midge, Contarinia oregonensis (Diptera: Ce-cidomyiidae). Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract revealed a single compound (A) that elicited responses from male antennae. Hydrogenation of pheromone extract, followed by renewed GC-EAD analysis, revealed a new EAD-active compound with chromatographic characteristics identical to those of tridecan-2-yl acetate on five fused silica columns (DB-5, DB-210, DB-23, SP-1000, and Cyclodex-B). Syntheses, chromatography, and retention index calculations of all possible tridecen-2-yl acetates suggested that the candidate pheromone A was a tridecadien-2-yl acetate with nonconjugated double bonds. Synthetic candidate pheromone component (Z,Z)-4,7-tridecadien-2-yl acetate (Z4Z7) cochromatographed with A on all analytical columns and elicited comparable antennal activity. In GC-EAD analyses that separated the enantiomers (Z,Z)-4,7-tridecadien-(S)-2-yl acetate (2S-Z4Z7) and (Z,Z)-4,7-tridecadien-(R)-2-yl acetate (2R-Z4Z7) with baseline resolution, only 2S-Z4Z7 as a component in a racemic standard or in pheromone extract elicited antennal responses. In Douglas-fir seed orchards, sticky traps baited with 2S-Z4Z7 captured male C. oregonensis, whereas 2R-Z4Z7 was behaviorally benign. Comparable catches of males in traps baited with racemic Z4Z7 (50 microg) or virgin female C. oregonensis suggested that synthetic pheromone baits could be developed for monitoring C. oregonensis populations in commercial Douglas-fir seed orchards.
Gries
Regine
R
Centre for Environmental Biology, Department of Biological Sciences, Simon Fraser University, Burnaby, British Columbia, V5A 1S6 Canada. gries@sfu.ca
Khaskin
Grigori
G
Gries
Gerhard
G
Bennett
Robb G
RG
King
G G Skip
GG
Morewood
Petra
P
Slessor
Keith N
KN
Morewood
W Dean
WD
D000085:Acetates / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004175:Diptera / Q000502:physiology*; D005260:Female; D008297:Male; D012724:Sex Attractants / Q000737:chemistry*; D012726:Sexual Behavior, Animal
C473094:4,7-tridecadien-2-yl acetate; D000085:Acetates; D000466:Alkadienes; D012724:Sex Attractants