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Journal of Chemical Ecology

, Volume 36, Issue 9, pp 969–977 | Cite as

Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden

  • Olle AnderbrantEmail author
  • Jan Löfqvist
  • Erik Hedenström
  • Joakim Bång
  • Akira Tai
  • Hans-Erik Högberg
Article

Abstract

The pine sawfly Neodiprion sertifer (Geoffroy) uses the acetate or propionate of (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol) as pheromone components, with the (2S,3R,7R)-isomer being antagonistic, synergistic, or inactive according to the population tested. In this study, we tested the attraction of males to the acetates of three analogs of diprionol, each missing one methyl group, viz. (2S,7S)-7-methyl-2-pentadecanol, (2S,6S)-2,6-dimethyl-1-tetradecanol, and (2S,3S)-3-methyl-2-pentadecanol. None of the analogs alone, or in combination with diprionol acetate, was attractive in Sweden, even at 100 times the amount of diprionol acetate attractive to N. sertifer. In Japan, the acetate of (2S,3S)-3-methyl-2-pentadecanol attracted males when tested in amounts 10–20 times higher than the acetate pheromone component. The acetate esters of the (2S,3R)-analog and the (2S,3R,7R)-isomer of diprionol also were tested in combination with the pheromone compound (acetate ester). Both compounds caused an almost total trap-catch reduction in Sweden, whereas in Japan they appear to have relatively little effect on trap capture when added to diprionol acetate. Butyrate and iso-butyrate esters of diprionol were unattractive to N. sertifer in Sweden. In summary, there exists geographic variation in N. sertifer in responses to both diprionyl acetate and some of its analogs.

Key Words

Hymenoptera Symphyta Diprionidae Semiochemical Sex attractant Behavioral response Pheromone trap Antagonist Geographic variation 

Notes

Acknowledgments

We thank Eva Annerfeldt, Erling Jirle, Rolf Wedding, and Fredrik Östrand for technical assistance. Financial support was provided by The Swedish Council for Forestry and Agricultural Research, The Swedish Natural Science Research Council, The Bank of Sweden Tercentenary Foundation, and Carl Tryggers Stiftelse för Vetenskaplig Forskning. We also are grateful for financial support from EU (Objective 1 the region of South Forest Counties) and Länsstyrelsen i Västernorrlands län.

References

  1. Anderbrant, O. 1993 Pheromone biology of sawflies. pp. 119–154, in M. R. Wagner and K. F. Raffa (eds.). Sawfly Life History Adaptations To Woody Plants. Academic Press, New York.Google Scholar
  2. Anderbrant, O. 1999. Sawflies and seed wasps. pp. 199–226, in R. J. Hardie, and A. K. Minks (eds.). Pheromones of Non-lepidopteran Insects Associated with Agricultural Plants. CAB International, Wallingford.Google Scholar
  3. Anderbrant, O., Löfqvist, J., Jönsson, J., and Marling, E. 1989. Effects of pheromone trap type, position and colour on the catch of the pine sawfly Neodiprion sertifer (Geoff.) (Hym., Diprionidae). J. Appl. Entomol. 107:365–369.CrossRefGoogle Scholar
  4. Anderbrant, O., Bengtsson, M., Löfqvist, J., and Baeckström, P. 1992a. Field response of the pine sawfly Neodiprion sertifer to controlled release of diprionyl acetate, diprionyl propionate and trans-perillenal. J. Chem. Ecol. 18:1707–1725.CrossRefGoogle Scholar
  5. Anderbrant, O., Löfqvist, J., Högberg, H.-E., Hedenström, E., Wassgren, A.-B., Bergström, G., Bengtsson M., and Magnusson, G. 1992b. Field response of the pine sawfly Neodiprion sertifer to the pheromone (2S,3S,7S)-diprionyl acetate and its stereoisomers. Entomol. Exp. Appl. 62:169–181.CrossRefGoogle Scholar
  6. Anderbrant, O., Hansson, B. S., Hallberg, E., Geri, C., Varama, M., Hedenström, E., Högberg, H.-E., Fägerhag, J., Edlund, H., Wassgren, A.-B., Bergström, G., and Löfqvist, J. 1995. Electrophysiological and morphological characteristics of pheromone receptors in male pine sawflies, Diprion pini (Hymenoptera: Diprionidae), and behavioural response to some compounds. J. Insect Physiol. 41:395–401.CrossRefGoogle Scholar
  7. Anderbrant, O., Zhang, Q.-H., and Chu, D. 1997. Diprionyl esters attractive to males of the Dailing pine sawfly Neodiprion dailingensis Xiao et Zhou (Hym., Diprionidae) in north-eastern China. J. Appl. Entomol. 21:281–283.CrossRefGoogle Scholar
  8. Anderbrant, O., Löfqvist, J., Högberg, H.-E., Hedenström, E., Baldassari, N., Baronio, P., Kolmakova, G., Lyons, B., Naito, T., Odinokov, V., Simandl, J., Supatashvili, A., Tai, A., and Tourianov, R. 2000. Geographic variation in the field response of male European pine sawflies, Neodiprion sertifer, to different pheromone stereoisomers and esters. Entomol. Exp. Appl. 95:229–239.CrossRefGoogle Scholar
  9. Anderbrant, O., Östrand, F., Bergström, G., Wassgren, A.-B., Auger-Rozenberg, M.-A., Geri, C., Hedenström, E., Högberg, H.-E., Herz, A., and Heitland, W. 2005. Release of sex pheromone and its precursors in the pine sawfly Diprion pini (Hym., Diprionidae). Chemoecology 15:147–151.CrossRefGoogle Scholar
  10. Bergström, G., Wassgren, A.-B., Anderbrant, O., Fägerhag, J., Edlund, H., Hedenström, E., Högberg, H.-E., Geri, C., Auger, M. A., Varama, M., Hansson, B. S., and Löfqvist, J. 1995. Sex pheromone of the pine sawfly Diprion pini (Hymenoptera: Diprionidae): Chemical identification, synthesis and biological activity. Experientia 51:370–380.CrossRefGoogle Scholar
  11. Hansson, B. S., van der Pers, J. N. C., Hedenström, E., Högberg, H.-E., Anderbrant, O., and Löfqvist, J. 1991. Sex pheromone perception in male pine sawflies, Neodiprion sertifer (Hymenoptera;Diprionidae). J. Comp. Physiol. A 168:533–538.CrossRefPubMedGoogle Scholar
  12. Hedenström, E., Högberg, H.-E., Wassgren, A.-B., Bergström, G., Löfqvist, J., Hansson, B. S., and Anderbrant, O. 1992. Sex pheromone of pine sawflies. Chiral synthesis of some active minor components isolated from Neodiprion sertifer and of some chiral analogues of diprionyl acetates. Tetrahedron 48:3139–3146.CrossRefGoogle Scholar
  13. Hedenström, E., Edlund, H., Lund, S., Abersten, M., and Persson, D. 2002. Synthesis and lipase catalysed stereoselective acylation of some 3-methyl-2-alkanols, identified as sex pheromone precursors in females of pine sawfly species. J. Chem. Soc. Perkin Trans. 1810–1817.Google Scholar
  14. Hedenström, E., Edlund, H., Wassgren, A.-B., Bergström, G., Anderbrant, O., Östrand, F., Sierpinski, A., Auger-rozenberg, M.-A., Herz, A., Heitland, W., and Varama, M. 2006. Sex pheromone of the pine sawfly Gilpinia pallida: chemical identification, synthesis and biological activity. J. Chem. Ecol. 32:2525–2541.CrossRefPubMedGoogle Scholar
  15. Hedenström, E., Edlund, H., Wassgren, A.-B., Bergström, G., Anderbrant, O., Östrand, F., Sierpinski, A., Auger-rozenberg, M.-A., Herz, A., Heitland, W., and Varama, M. 2009. The sex pheromones of two pine sawfly species Gilpinia frutetorum and Gilpinia socia: chemical identification, synthesis and biological activity. Zeitschrift für Naturforschung C 64c:733–742.Google Scholar
  16. Högberg, H.-E., Hedenström, E., Wassgren, A.-B., Hjalmarsson, M., Bergström, G., Löfqvist, J., and Norin, T. 1990. Synthesis and gas chromatographic separation of the eight stereoisomers of diprionol and their acetates, components of the sex pheromone of pine sawflies. Tetrahedron 46:3007–3018.CrossRefGoogle Scholar
  17. Norinder, U., Gustavsson, A.-L., and Liljefors, T. 1997. A 3D-QSAR study of analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum. J. Chem. Ecol. 23:2917–2934.CrossRefGoogle Scholar
  18. Tai, A., Morimoto, N., Yoshikawa, M., Uehara, K., Sugimura, T., and Kikukawa, T. 1990. Preparation of stereochemically pure sex pheromone components of the pine sawfly Neodiprion sertifer and field tests of the synthetic compounds. Agric. Biol. Chem. 54:1753–1762.Google Scholar
  19. Tai, A., Sugimura, T., Kikukawa, T., Naito, C., Nishimoto, Y., and Morimoto, N. 1992. Synthesis and field test of a pheromone mimic of the pine sawfly (Neodiprion sertifer). Biosci. Biotech. Biochem. 56:1711–1714.CrossRefGoogle Scholar
  20. Tai, A., Syouno, E., Tanaka, K., Fujita, M., Sugimura, T., Higashiura, Y., Kakizaki, M., Hara, H., and Naito, T. 2002. Regio- and stereochemical study of the sex pheromone of pine sawfly: Diprion nipponica. Bull. Chem. Soc. Jpn. 75:111–121.CrossRefGoogle Scholar
  21. Wassgren, A.-B., Anderbrant, O., Löfqvist, J., Hansson, B. S., Bergström, G., Hedenström, E., and Högberg, H.-E. 1992. Pheromone related compounds in pupal and adult female pine sawflies, Neodiprion sertifer, of different age and in different parts of the body. J. Insect Physiol. 38:885–893.CrossRefGoogle Scholar
  22. Wassgren, A.-B., Bergström, G., Sierpinski, A., Anderbrant, O., Högberg, H.-E., and Hedenström, E. 2000. Sex pheromone of the pine sawfly Macrodiprion nemoralis (Hymenoptera: Diprionidae): Identification of (2S,3R,7R,9S)-3,7,9-trimethyl-2-tridecanol as the precursor for the active pheromone acetate. Naturwissenshaften 87:24–29.CrossRefGoogle Scholar
  23. Zhang, Z., Wang, H., Chen, G., Anderbrant, O., Zhang, Y., Zhou, S., Hedenström, R., and Högberg, H.-E. 2005. Sex pheromone for monitoring flight periods and population densities of the pine sawfly, Diprion jingyuanensis Xiao et Zhang (Hym., Diprionidae). J. Appl. Entomol. 129:368–374.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Olle Anderbrant
    • 1
    Email author
  • Jan Löfqvist
    • 2
  • Erik Hedenström
    • 3
  • Joakim Bång
    • 3
  • Akira Tai
    • 4
    • 5
  • Hans-Erik Högberg
    • 3
  1. 1.Department of BiologyLund UniversityLundSweden
  2. 2.Department of Plant Protection ScienceSwedish University of Agricultural SciencesAlnarpSweden
  3. 3.Department of Natural Sciences, Engineering and MathematicsMid Sweden UniversitySundsvallSweden
  4. 4.Faculty of ScienceHimeji Institute of TechnologyHyogoJapan
  5. 5.OsakaJapan

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