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CHEMOECOLOGY

, Volume 14, Issue 3–4, pp 217–223 | Cite as

Identification, synthesis and activity of sex pheromone gland components of the autumn gum moth (Lepidoptera: Geometridae), a defoliator of Eucalyptus

  • Martin J. SteinbauerEmail author
  • Fredrik Östrand
  • Tom E. Bellas
  • Anna Nilson
  • Fredrik Andersson
  • Erik  Hedenström
  • Michael J. Lacey
  • P. Florian Schiestl
Research Papers

Summary.

The autumn gum moth, Mnesampela privata (Guenée) (Lepidoptera: Geometridae), is native to Australia and can be a pest of plantation eucalypts. Field-collected and laboratory-reared female autumn gum moths were dissected to remove glands likely to contain components of the sex pheromone. Using gas chromatography (GC) and combined gas chromatography–mass spectrometry (GC-MS), three compounds were identified from female extracts, namely (3Z,6 Z,9 Z)-3,6,9-nonadecatriene, 1-hexadecanol and 1-octadecanol (confirmed by comparison with synthetic samples). Nonadecatriene elicited an antennal response in male autumn gum moth during gas chromatographic analyses combined with electroantennographic detection (GC-EAD). In electroantennogram (EAG) recording male M. privata antennae responded to the nonadecatriene. Nonadecatriene was synthesised via Kolbe electrolysis, starting with (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid (linolenic acid) and propanoic acid or via an alternative four-step method also starting from linolenic acid. In field trials (3Z,6Z,9Z)-3,6,9-nonadecatriene proved attractive to male moths. Thus, we conclude that (3Z,6Z,9Z)-3,6,9- nonadecatriene is a sex pheromone component of autumn gum moth. This component has been identified in extracts from other geometrids in the same subfamily, Ennominae. However, to our knowledge this is the first example where (3Z,6Z,9Z)-3,6,9-nonadecatriene has been found in females and also proved attractive to male moths when presented on its own. Our results are discussed in relation to other geometrid pheromones.

Key words.

(3Z,6Z,9Z)-3,6,9-nonadecatriene gas chromatography mass spectrometry  GC–EAD, EAG, synthesis 

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Copyright information

© Birkhäuser-Verlag 2004

Authors and Affiliations

  • Martin J. Steinbauer
    • 1
    Email author
  • Fredrik Östrand
    • 2
  • Tom E. Bellas
    • 3
  • Anna Nilson
    • 4
  • Fredrik Andersson
    • 4
  • Erik  Hedenström
    • 4
  • Michael J. Lacey
    • 3
  • P. Florian Schiestl
    • 5
    • 6
  1. 1.Co-operative Research Centre (CRC) for Sustainable Production Forestry and CSIRO EntomologyCanberraAustralia
  2. 2.Chemical Ecology and Ecotoxicology, Department of Ecology Lund UniversityLundSweden
  3. 3.CSIRO EntomologyCanberraAustralia
  4. 4.Department of Natural and Environmental Sciences Mid Sweden UniversitySundsvallSweden
  5. 5.Department of Evolutionary Biology University of Vienna and School of Botany and Zoology, Australian National UniversityCanberraAustralia
  6. 6.Geobotanical InstituteETHZürichSwitzerland

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