Abstract
The honey locust gall midge, Dasineura gleditchiae Osten Sacken 1866 (Diptera: Cecidomyiidae) is the main pest of ornamental varieties of the honey locust tree, Gleditsia triacanthos L., in North America, and is now becoming a pest of concern in Europe. Female midges were observed to emerge in the early morning with their ovipositor extended until they mated. Volatiles were collected from virgin females in a closed-loop stripping apparatus and analyzed by gas chromatography (GC) coupled to electroantennographic (EAG) recording from the antenna of a male midge. A single EAG response was observed, which was assumed to be to the major component of the female sex pheromone. This was identified as (Z)-2-acetoxy-8-heptadecene by comparison of its mass spectrum and GC retention times on different columns with those of synthetic standards and by micro-analytical reactions. This compound was synthesized, and the individual enantiomers were produced by kinetic resolution with lipase from Candida antarctica. Analysis of the naturally-produced compound on a cyclodextrin GC column indicated it was the (R)-enantiomer. In EAG dose-response measurements, the (R)-enantiomer alone or in the racemic mixture evoked significant responses from the antennae of male D. gleditchiae, whereas the (S)-enantiomer did not. In field trapping tests, the (R)-enantiomer attracted male D. gleditchiae. The racemic compound was equally attractive, but the (S)-enantiomer was not attractive. Both the pure (R)-enantiomer or racemic (Z)-2-acetoxy-8-heptadecene, applied to red rubber septa in a dose range of 3–30 μg, constitute a strongly attractive bait in sticky traps for monitoring the flight of D. gleditchiae.
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Acknowledgements
This work was sponsored in part by a grant of NKFP 4/012/2004 and by a grant of the Hungarian Scientific Research Fund (OTKA) K 72767 to G. Szőcs. The GC-EAD apparatus was financed by GVOP-3.2.1-2004-04-0153/3.0 (major part) and by OTKA T37355 (minor part) to G. Szőcs. We are grateful to G. Gries for a sample of (2S,12Z)-2-acetoxy-12-heptadecene.
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Molnár, B., Kárpáti, Z., Szőcs, G. et al. Identification of Female-produced Sex Pheromone of the Honey Locust Gall Midge, Dasineura gleditchiae . J Chem Ecol 35, 706–714 (2009). https://doi.org/10.1007/s10886-009-9641-5
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DOI: https://doi.org/10.1007/s10886-009-9641-5