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.
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.
Bengtsson, M. and Liljefors, T. 1988. DMPU: An alternative to HMPT in moth sex pheromone synthesis. Synthesis 1988:250–252.
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.
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.
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.
Coutts, M. P. and Dolezal, J. E. 1969. Emplacement of fungal spores by the woodwasp, Sirex noctilio, during oviposition. Forest Sci. 15:412–416.
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.
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.
Francis, G. W. and Veland, K. 1981. Alkylthiolation for the determination of double-bond positions in linear alkanes. J. Chrom. 219:379–384.
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.
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.
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.
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.
Howard, R. W. and Blomquist, G. J. 2005. Ecological, behavioral, and biochemical aspects of insect hydrocarbons. Annu. Rev. Entomol. 50:371–93.
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.
Keeling, Ch. I., Plettner, E., and Slessor, K. N. 2004. Hymenopteran semiochemicals. Top. Curr. Chem. 239:133–177.
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.
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.
Madden, J. L. 1981. Egg and larval development in the woodwasp, Sirex noctilio F. Aust. J. Zool. 29: 493–506.
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.
Morgan, F. D. 1968. Bionomics of Siricidae. Annu. Rev. Entomol. 13:239–256.
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.
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.
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.
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.
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.
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.
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.
Wyatt, T. D., 2003. Pheromones and Animal Behavior: Communication by Smell and Taste, pp. 70–73, pp. 102–109. Cambridge University Press, Cambridge, UK.
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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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