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Identification of female-produced sex pheromone of the honey locust gall midge, Dasineura gleditchiae

Identification of female-produced sex pheromone of the honey locust gall midge, Dasineura gleditchiae

Molnár, Béla, Kárpáti, Zsolt, Szőcs, Gábor and Hall, David R. ORCID: 0000-0002-7887-466X (2009) Identification of female-produced sex pheromone of the honey locust gall midge, Dasineura gleditchiae. Journal of Chemical Ecology, 35 (6). pp. 706-714. ISSN 0098-0331 (Print), 1573-1561 (Online) (doi:https://doi.org/10.1007/s10886-009-9641-5)

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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.

Item Type: Article
Additional Information: [1] Published online: 21 May 2009. [2] Published in print: 1 June 2009. [3] Published as: Journal of Chemical Ecology, (2009), Vol. 35, (6), pp. 706-714. [4] Original spelling: Szőcs, Gábor.
Uncontrolled Keywords: honey locust gall midge, Dasineura gleditchiae, cecidomyiidae, chiral sex pheromone, enantiomers, (Z)-2-acetoxy-8-heptadecene, (2R,8Z)-2-acetoxy-8-heptadecene, Gleditsia triacanthos, ornamental tree, diptera
Subjects: S Agriculture > S Agriculture (General)
S Agriculture > SF Animal culture
S Agriculture > SB Plant culture
Faculty / Department / Research Group: Faculty of Engineering & Science > Natural Resources Institute
Faculty of Engineering & Science > Natural Resources Institute > Agriculture, Health & Environment Department
Related URLs:
Last Modified: 03 Jul 2013 14:16
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
Selected for GREAT 2019: None
URI: http://gala.gre.ac.uk/id/eprint/2060

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