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Identification of the Female-Produced Sex Pheromone of Tischeria ekebladella, an Oak Leafmining Moth

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Abstract

The native leafmining moth Tischeria ekebladella (Lepidoptera: Tischeriidae) feeds on oaks and recently has become a pest of silviculture and urban green areas in central Europe. The behavioral responses of male moths to hexane extracts of whole bodies of calling females or males were tested under laboratory conditions. Only extracts of females elicited responses from males. Analysis of extracts by coupled gas chromatography/electroantennographic detection revealed the presence of two electroantennogram-active peaks. Structure elucidation of these compounds, by gas-chromatography/mass spectrometry and independent synthesis revealed them to be (3Z,6Z,9Z)-tricosa-3,6,9-triene and (3Z,6Z,9Z,19Z)-tricosa-3,6,9,19-tetraene. While the triene was present in both sexes, the tetraene was female-specific. The latter is a new structure for a pheromone component of Lepidoptera and a novel natural product. Field trapping tests, carried out in a mixed oak forest near Budapest (Hungary), using synthetic compounds applied to rubber dispensers, showed that the tetraene per se elicited catches of males in large numbers. When the triene was added to the tetraene in a ratio of 1:1, there was no increase in trap catch; the triene alone did not elicit catches of males. For monitoring this insect, the tetraene, applied to rubber dispensers at a dose of 300 μg, is a potent sex attractant.

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Acknowledgements

This work was sponsored in part by the Hungarian National Scientific Fund OTKA 72767 to Dr. Szőcs. The GC-EAD apparatus was financed by MAG GVOP-3.2.1-2004-04-0153/3.0 (major part) and by OTKA T37355 (minor part), while the IDAC 232 amplifier was a gift from the late Dr. Jan van der Pers (Syntech, Hilversum, the Netherlands) to Dr. Szőcs. Prof. Subchev and Dr. Toshova are grateful to the financial support of the Bulgarian National Scientific Fund, Grants B-1201/2002 and DO02-244/2008.

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Authors and Affiliations

  1. Plant Protection Institute, Centre for Agricultural Research, Hungarian Academy of Sciences, Budapest, Pf 102, 1525, Hungary

    Béla Péter Molnár, Gábor Szőcs & Miklós Tóth

  2. Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Armin Tröger & Wittko Francke

  3. Institute of Biodiversity and Ecosystem Research, Bulgarian Academy of Sciences, ul. Gagarin 2, Sofia, 1113, Bulgaria

    Theodora B. Toshova & Mitko Subchev

  4. Department of Terrestrial Zoology, Naturalis Biodiversity Center, PO Box 9517, 2300 RA, Leiden, Netherlands

    Erik J. van Nieukerken & J. C. (Sjaak) Koster

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  1. Béla Péter Molnár
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  2. Armin Tröger
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  3. Theodora B. Toshova
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  9. Wittko Francke
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Correspondence to Gábor Szőcs.

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Molnár, B.P., Tröger, A., Toshova, T.B. et al. Identification of the Female-Produced Sex Pheromone of Tischeria ekebladella, an Oak Leafmining Moth. J Chem Ecol 38, 1298–1305 (2012). https://doi.org/10.1007/s10886-012-0184-9

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