Skip to main content
Log in

Ethyl 4-Methyl Heptanoate: A Male-Produced Pheromone of Nicrophorus vespilloides

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

Sexually mature male beetles of the genus Nicrophorus (Coleoptera: Silphidae) exhibit a conspicuous behavior, recognized as pheromone-releasing activity. Laboratory and field studies demonstrated that females are attracted to males that exhibit this behavior, both on or off reproductive resources. Here, we report the results of a study in which volatile chemicals released by calling Nicrophorus vespilloides were collected by solid-phase microextraction and analyzed by using coupled gas chromatography–mass spectrometry. These analyses revealed that ethyl 4-methyl heptanoate and (E)-geranylacetone are emitted by males that engage in the behavior. In the field, traps baited with racemic ethyl 4-methyl heptanoate caught roughly equal numbers of male and female N. vespilloides. Some male and female Nicrophorus vespillo and male Nicrophorus humator were also caught in traps baited with this compound. Traps baited with (E)-geranylacetone did not catch significant numbers of beetles.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1

Similar content being viewed by others

References

  • Beeler, A. E., Rauter, C. M., and Moore, A. J. 1999. Pheromonally mediated mate attraction by males of the burying beetle Nicrophorus orbicollis: Alternative calling tactics conditional on both intrinsic and extrinsic factors. Behav. Ecol. 10:578–584.

    Article  Google Scholar 

  • Beeler, A. E., Rauter, C. M., and Moore, A. J. 2002. Mate discrimination by females in the burying beetle Nicrophorus orbicollis: The influence of male size on attractiveness to females. Ecol. Entomol. 27:1–6.

    Article  Google Scholar 

  • Eggert, A.-K. 1992. Alternative male mate-finding tactics in burying beetles. Behav. Ecol. 3:243–254.

    Article  Google Scholar 

  • Eggert, A.-K., and Müller, J. K. 1989a. Pheromone-mediated attraction in burying beetles. Ecol. Entomol. 14:235–238.

    Google Scholar 

  • Eggert, A.-K., and Müller, J. K. 1989b. Mating success of pheromone-emitting Necrophorus males: Do attracted females discriminate against resource owners? Behaviour 110:248–257.

    Google Scholar 

  • Eggert, A.-K., and Müller, J. K. 1997. Biparental care and social evolution in burying beetles: Lessons from the larder, pp. 216–236, in: J. C. Choe and B. J. Crespi (eds.). Social Behavior in Insects and Arachnids. Cambridge University Press, Cambridge.

    Google Scholar 

  • Eisner, T., and Meinwald, J. 1982. Defensive spray mechanism of a silphid beetle (Necrodes surinamensis). Psyche 89:357–368.

    Article  Google Scholar 

  • Eisner, T., Deyrup, M., Jacobs, R., and Meinwald, J. 1986. Necrodols: Anti-insectan terpenes from defensive secretion of carrion beetle (Necrodes surinamensis). J. Chem. Ecol. 12:1407–1415.

    Article  CAS  Google Scholar 

  • Francke, W., and Dettner, K. 2005. Chemical signalling in beetles. Topics in current chemistry, pp. 85–166. Springer-Verlag, Berlin.

    Google Scholar 

  • Hallett, R. H., Perez, A. L., Gries, G., Gries, R., Pierce, H. D., Jr., Yue, J., Oehlschlager, A. C., Gonzalez, L. M., and Borden, J. H. 1995. Aggregation pheromone of coconut rhinoceros beetle, Oryctes rhinoceros (L.) (Coleoptera: Scarabaeidae). J. Chem. Ecol. 21:1549–1570.

    Article  CAS  Google Scholar 

  • Joung, M. J., Ahn, J. H., Lee, D. W., and Yoon, N. M. 1998. Coupling reaction of alkenes with α-bromo carboxylic acid derivatives using nickel boride and borohydride exchange resin in methanol. J. Org. Chem. 63:2755–2757.

    Article  PubMed  CAS  Google Scholar 

  • Meinwald, J., Roach, B., Hicks, K., Alsop, D., and Eisner, T. 1985. Defensive steroids from a carrion beetle (Silpha americana). Experientia 41:516–519.

    Article  PubMed  CAS  Google Scholar 

  • Meinwald, J., Roach, B., and Eisner, T. 1987. Defensive steroids from a carrion beetle (Silpha novaboracensis). J. Chem. Ecol. 13:35–38.

    Article  CAS  Google Scholar 

  • Mosebach, E. 1936. Aus dem Leben des Totengräbers (Necrophorus). Nat. Volk 66:222–231.

    Google Scholar 

  • Müller, J. K., and Eggert, A.-K. 1987. Effects of carrion-independent pheromone emission by male burying beetles (Silphidae: Necrophorus). Ethology 76:297–304.

    Article  Google Scholar 

  • Müller, J. K., Braunisch, V., Hwang, W., and Eggert, A.-K. 2007. Alternative tactics and individual reproductive success in natural associations of the burying beetle, Nicrophorus vespilloides. Behav. Ecol. 18:196–203.

    Article  Google Scholar 

  • Otronen, M. 1988. The effect of body size on the outcome of fights in burying beetles (Nicrophorus). Ann. Zool. Fenn. 25:191–201.

    Google Scholar 

  • Peschke, K., Friedrich, P., Kaiser, U., Franke, S., and Francke, W. 1999. Isopropyl (Z9)-hexadecenoate as a male attractant pheromone from the sternal gland of the rove beetle Aleochara curtula (Coleoptera: Staphylinidae). Chemoecology 9:47–54.

    Article  CAS  Google Scholar 

  • Pukowski, E. 1933. Ökologische Untersuchungen an Necrophorus F. Z. Morphol. Okol. Tiere 27:518–586.

    Article  Google Scholar 

  • Roach, B., Eisner, T., and Meinwald, J. 1990. Defense mechanisms of arthropods. 83. Alpha- and beta-necrodol, novel terpenes from a carrion beetle (Necrodes surinamensis, Silphidae, Coleoptera). J. Org. Chem. 55:4047–4051.

    Article  CAS  Google Scholar 

  • Scott, M. P. 1998. The ecology and behavior of burying beetles. Annu. Rev. Entomol. 43:595–618.

    Article  PubMed  CAS  Google Scholar 

  • Wertheim, B., Van Baalen, E. J. A., Dicke, M., and Vet, L. E. M. 2005. Pheromone-mediated aggregation in nonsocial arthropods: An evolutionary ecological perspective. Annu. Rev. Entomol. 50:321–346.

    Article  PubMed  CAS  Google Scholar 

  • Woodard, C. B. S. 2006. Odor masking of a vertebrate carcass by a burying beetle (Nicrophorus marginatus). Master’s thesis, Texas Tech University.

Download references

Acknowledgments

We thank Anne-Katrin Eggert and Stephen Ellis for valuable comments on the manuscript.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Wolf Haberer.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Haberer, W., Schmitt, T., Peschke, K. et al. Ethyl 4-Methyl Heptanoate: A Male-Produced Pheromone of Nicrophorus vespilloides . J Chem Ecol 34, 94–98 (2008). https://doi.org/10.1007/s10886-007-9406-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10886-007-9406-y

Keywords

Navigation