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Monoalkenes as Contact Sex Pheromone Components of the Woodwasp Sirex noctilio

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Abstract

A pheromone on the cuticle of females of the woodwasp Sirex noctilio, a recently introduced pest of pines in North America, induces conspecific males to attempt copulation. Dead females washed with hexane did not elicit copulation attempts from males, whereas reapplication of a female hexane body wash onto the cuticle of dead females elicited copulation attempts by 65% of males tested. Analysis of the hexane extract revealed saturated and unsaturated hydrocarbons as major components of the female cuticle. Behavior-guided fractionation of the female body wash led to the identification of three components, (Z)-7-heptacosene, (Z)-7-nonacosene, and (Z)-9-nonacosene, of the sex pheromone of S. noctilio that elicited copulatory responses from males.

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References

  • Alcock, J. and Dodson, G. 2008. The diverse mating systems of hilltopping insects. Am. Entomol. 54:80–87.

    Google Scholar 

  • Ayasse, M., Paxton, R. J., and Tengö, J. 2001. Mating behavior and chemical communication in the order of Hymenoptera. Annu. Rev. Entomol. 46:31–78.

    Article  CAS  PubMed  Google Scholar 

  • Bengtsson, M. and Liljefors, T. 1988. DMPU: An alternative to HMPT in moth sex pheromone synthesis. Synthesis 1988:250–252.

    Article  Google Scholar 

  • Blomquist, G. J., Tillman-Wall, J. A., Guo, L., Quilici, D. R., Gu, P., and Schal, C 1993. Hydrocarbon and hydrocarbon derived sex pheromones in insects: biochemistry and endocrine regulation, pp. 317–351, in D. W. Stanley-Samuelson, D. R. Nelson (eds.). Insect Lipids: Chemistry, Biochemistry and Biology. University of Nebraska Press, Lincoln, Nebraska.

    Google Scholar 

  • Böröczky, K., Park, K. -Ch., Minard, R. D., Jones, T. H., Baker, Th. C., and Tumlinson, J. H. 2008. Differences in the cuticular lipid composition of the antennae of Helicoverpa zea, Heliothis virescens, and Manduca sexta. J. Ins. Physiol. 54:1385–1391.

    Article  Google Scholar 

  • Carlson, D. A., Bernier, U. R., and Sutton, B. D. 1998. Elution patterns from capillary GC for methyl-branched alkanes. J. Chem. Ecol. 24:1845–1865.

    Article  CAS  Google Scholar 

  • Coutts, M. P. and Dolezal, J. E. 1969. Emplacement of fungal spores by the woodwasp, Sirex noctilio, during oviposition. Forest Sci. 15:412–416.

    Google Scholar 

  • Crook, D. J., Kerr, L. M., and Mastro, V. C. 2008. Sensilla on the antennal flagellum of Sirex noctilio (Hymenoptera: Siricidae). Ann. Entomol. Soc. Am. 101:1094–1102.

    Article  Google Scholar 

  • Fong, L. K. and Crowden, R. K. 1973. Physiological effects of mucus from the wood wasp, Sirex noctilio F., on the foliage of Pinus radiata D. Don. Australian J. Biol. Sci. 26:365–378.

    Google Scholar 

  • Francis, G. W. and Veland, K. 1981. Alkylthiolation for the determination of double-bond positions in linear alkanes. J. Chrom. 219:379–384.

    Article  CAS  Google Scholar 

  • Ginzel, M. D., Millar, J. G., and Hanks, L. M. 2003. (Z)-9-Pentacosene — contact sex pheromone of the locust borer, Megacyllene robiniae. Chemoecology 13:135–141.

    Article  CAS  Google Scholar 

  • Ginzel, M. D., Moreira, J. A., Ray, A. M., Millar, J. G., and Hanks, L. M. 2006. (Z)-9-Nonacosene—major component of the contact sex pheromone of the beetle Megacyllene caryae. J. Chem. Ecol. 32:435–451.

    Article  CAS  PubMed  Google Scholar 

  • Hoebeke, E. R., Haugen, D. A., and Haack, R. A. 2005. Sirex noctilio: Discovery of a Palearctic siricid woodwasp in New York. Newsletter of the Michigan Entomol. Soc. 50:24–25.

    Google Scholar 

  • Howard, R. W. 1993. Cuticular hydrocarbons and chemical communication, pp. 179–226, in D. W. Stanley-Samuelson, D. R. Nelson (eds.). Insect Lipids: Chemistry, Biochemistry and Biology. University of Nebraska Press, Lincoln, Nebraska.

    Google Scholar 

  • Howard, R. W. and Blomquist, G. J. 2005. Ecological, behavioral, and biochemical aspects of insect hydrocarbons. Annu. Rev. Entomol. 50:371–93.

    Article  CAS  PubMed  Google Scholar 

  • Hurley, B. P, Slippers, B., and Wingfield, M. J. 2007. A comparison of control results for the alien invasive woodwasp Sirex noctilio, in the southern hemisphere. Agric. Forest Entomol. 9: 159–171.

    Article  Google Scholar 

  • Keeling, Ch. I., Plettner, E., and Slessor, K. N. 2004. Hymenopteran semiochemicals. Top. Curr. Chem. 239:133–177.

    Article  CAS  Google Scholar 

  • Kovats, E. sz. 1965. Gas chromatographic characterization of organic substances in the retention index system, pp. 229–247, in J. C. Giddings, R. A. Keller (eds.). Advances in Chromatography, M. Dekker Inc, New York.

    Google Scholar 

  • Li, T. -S., Li, J. -T., and Li, H. -Z. 1995. Modified and convenient preparation of silica impregnated with silver nitrate and its application to the separation of steroids and triterpenes. J. Chrom. A 715:372–375.

    Article  CAS  Google Scholar 

  • Madden, J. L. 1981. Egg and larval development in the woodwasp, Sirex noctilio F. Aust. J. Zool. 29: 493–506.

    Article  Google Scholar 

  • Marukawa, K., Takikawa, H., and Mori, K. 2001. Synthesis of the enantiomers of some methyl-branched cuticular hydrocarbons of the ant Diacamma sp. Biosci. Biotechnol. Biochem. 65:305–314.

    Article  CAS  PubMed  Google Scholar 

  • Morgan, F. D. 1968. Bionomics of Siricidae. Annu. Rev. Entomol. 13:239–256.

    Article  Google Scholar 

  • Morgan, F. D. and Stewart, N. C. 1966. The biology and behaviour of the woodwasp Sirex noctilio F. in New Zealand. Trans. roy. Soc. N. Z., Zool. 7:195–204.

    Google Scholar 

  • Mori, K. and Wu, J. 1992. Synthesis of the four possible stereoisomers of 13,17-dimethylnonatriacontane, a kairomone for the wasp Trichogramma nubilale. Liebigs Ann. Chem. 1992:83–85.

    Article  Google Scholar 

  • Nelson, D. R. 2001. Discovery of novel trimethylalkanes in the internal hydrocarbons of developing pupae of Heliothis virescens and Helicoverpa zea. Comp. Biochem. Physiol. Part B 128:647–659.

    Article  CAS  Google Scholar 

  • Simpson, R. F. 1976. Bioassay of pine oil components as attractants for Sirex noctilio (Hymenoptera: Siricidae) using electroantennogram techniques. Ent. Exp. Appl. 19:11–18.

    Article  CAS  Google Scholar 

  • Taylor, K. L. 1981. The sirex woodwasp: Ecology and control of an introduced forest insect, pp. 231–248, in R. L. Kitching and R. E. Jones (eds.). The Ecology of Pests — Some Australian Case Histories. CSIRO, Melbourne, Australia.

    Google Scholar 

  • Van Den Dool, H. and Kratz, P. D. 1963. A generalization of the retention index system including linear temperature programmed gas—liquid partition chromatography. J. Chrom. 11:463–471.

    Article  Google Scholar 

  • Vincenti, M., Guglielmetti, G., Cassani, G., and Tonini, C. 1987. Determination of double bond position in diunsaturated compounds by mass spectrometry of dimethyl disulfide derivatives, Anal. Chem. 59:694–699.

    Article  Google Scholar 

  • Wyatt, T. D., 2003. Pheromones and Animal Behavior: Communication by Smell and Taste, pp. 70–73, pp. 102–109. Cambridge University Press, Cambridge, UK.

    Google Scholar 

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Acknowledgements

This research was supported by USDA APHIS PPQ. We thank Robert D. Minard at the Proteomics and Mass Spectrometry Core Facility at The Huck Institutes of the Life Sciences of The Pennsylvania State University very kindly for providing the high resolution mass spectrometry data.

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Correspondence to Katalin Böröczky.

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Böröczky, K., Crook, D.J., Jones, T.H. et al. Monoalkenes as Contact Sex Pheromone Components of the Woodwasp Sirex noctilio . J Chem Ecol 35, 1202–1211 (2009). https://doi.org/10.1007/s10886-009-9693-6

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  • DOI: https://doi.org/10.1007/s10886-009-9693-6

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