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Chemoecology

, Volume 20, Issue 3, pp 179–187 | Cite as

Pheromone of the elm bark beetle Scolytus laevis (Coleoptera: Scolytidae): stereoisomers of 4-methyl-3-heptanol reduce interspecific competition

  • Olle Anderbrant
  • Donald S. Matteson
  • C. Rikard Unelius
  • Philip S. Pharazyn
  • Ellen M. Santangelo
  • Fredrik Schlyter
  • Göran Birgersson
Research Paper

Abstract

Stereoisomers of 4-methyl-3-heptanol (MH) are pheromone components of several Scolytus bark beetles. The elm bark beetle Scolytus laevis (Coleoptera: Scolytidae) has in previous studies been caught in traps baited with commercial MH containing all four stereoisomers, but the lure has been considered a weak attractant. In this study, we addressed the question whether stereospecific responses by S. laevis to stereoisomers of MH might contribute to its niche separation from other sympatric Scolytus species. Using GC–MS, we analyzed extracts of hindguts and abdomens from male and female S. laevis and the sympatric S. triarmatus. We also tested all four MH-stereoisomers individually and in combinations in the field to determine their role for S. laevis. All four stereoisomers were synthesized via a boronic ester method with 1,2-dicyclohexylethanediol as chiral director. In addition, the (3S,4R)-stereoisomer of MH was prepared through enantioselective, lipase-mediated transesterification of a mixture of the four stereoisomers of MH. Females of both species contained small amounts of syn-MH, and males contained trace amounts of anti-MH. The anti stereoisomer (3R,4S)-MH was attractive to male and female S. laevis, whereas the syn stereoisomer (3S,4S)-MH acted as an inhibitor or deterrent and reduced the catch when added to the attractive isomer. The syn isomer is the main aggregation pheromone component of the larger and sympatric S. scolytus and possibly also of S. triarmatus. The avoidance response of S. laevis to the (3S,4S)-stereoisomer may reduce interspecific competition for host trees.

Keywords

Semiochemical Attractant Chemical analysis Synthesis Scolytus triarmatus Dutch elm disease 

Notes

Acknowledgments

We thank Annika Söderman, Björn Johansson and Fredrik Östrand for assistance during fieldwork, two anonymous reviewers for valuable comments and C. F. Lundströms Stiftelse and The Royal Swedish Academy of Agriculture and Forestry for financial support.

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Copyright information

© Springer Basel AG 2010

Authors and Affiliations

  • Olle Anderbrant
    • 1
  • Donald S. Matteson
    • 2
  • C. Rikard Unelius
    • 3
  • Philip S. Pharazyn
    • 2
  • Ellen M. Santangelo
    • 4
  • Fredrik Schlyter
    • 1
    • 6
  • Göran Birgersson
    • 5
    • 6
  1. 1.Department of BiologyLund UniversityLundSweden
  2. 2.Department of ChemistryWashington State UniversityPullmanUSA
  3. 3.School of Natural SciencesLinneus UniversityKalmarSweden
  4. 4.Department of ChemistryRoyal Institute of TechnologyStockholmSweden
  5. 5.Department of Chemical EcologyGöteborg UniversityGöteborgSweden
  6. 6.Chemical Ecology, Department of Plant Protection BiologySwedish University of Agricultural SciencesAlnarpSweden

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