A Male-produced Sex Pheromone from the Neotropical Redbanded Stink Bug, Piezodorus guildinii (W.)

  • Miguel Borges
  • Jocelyn G. Millar
  • R. A. Laumann
  • Maria C. B. Moraes


The male-produced sex pheromone of the neotropical redbanded stink bug, Piezodorus guildinii (W.) (Hemiptera: Pentatomidae), a serious pest of soybean in Central and South America, was identified as the sesquiterpene hydrocarbon β-sesquiphellandrene by coupled gas chromatography–mass spectrometry and laboratory bioassays. The identity was confirmed by comparison with an authentic standard, and its absolute configuration was determined to be (7R)-(+)-β-sesquiphellandrene. The mean rate of release was approximately 40 ng d−1 male−1. The compound was found only in extracts from sexually mature males. Laboratory olfactometer bioassays showed that 200 ng of the synthetic compound applied to a filter paper strip was as attractive to female bugs as odors from five 15-d-old live males, an airborne extract from males, or the fraction of the extract that contained (7R)-(+)-β-sesquiphellandrene.


Soybean pest Sex pheromone β-Sesquiphellandrene Olfactometer bioassay 



We thank Hélio Santos, Diva Tiburcio, and Camila Raquel for helping with field collection and laboratory rearing of the insects used in this study. This work received financial support from the Brazilian Council for Scientific and Technological Development (CNPq), Distrito Federal Research Foundation (FAPDF), and EMBRAPA. This research was also supported by the International Foundation for Science, Stockholm, Sweden, through a grant to Maria Carolina Blassioli Moraes.


  1. Aldrich, J. R., Numata, H., Borges, M., Bin, F., Waite, G. K., and Lusby, W. R. 1993. Artifacts and pheromone blends from Nezara spp. and other stink bugs (Heteroptera: Pentatomidae). Z. Naturforsch. 48C:73–79.Google Scholar
  2. Borges, M. and Aldrich, J. R. 1992. Instar-specific defensive secretions of stink bugs (Heteroptera: Pentatomidae). Experientia 48:893–896.CrossRefGoogle Scholar
  3. Borges, M. and Bldrich, J. R. 1994. Attractant pheromone for nearctic stink bug, Euschistus obscurus (Heteroptera: Pentatomidae): insight into a neotropical relative. J. Chem. Ecol. 20:1095–1102.CrossRefGoogle Scholar
  4. Borges, M., Mori, K., Costa, M. L. M., and Sujii, E. R. 1998a. Behavioural evidence of methyl-2,6,10-trimethyltridecanoate as a sex pheromone of Euschistus heros (Heteroptera: Pentatomidae). J. Appl. Entomol. 122:335–338.CrossRefGoogle Scholar
  5. Borges, M., Schmidt, F. G. V., Sujii, E. R., Medeiros, M. A., Mori, K., Zarbin, P. H. G., and Ferreira, T. B. 1998b. Field responses of stink bugs to the natural and synthetic pheromone of the neotropical brown stink bug, Euschistus heros (Heteroptera: Pentatomidae). Physiol. Entomol. 23:202–207.CrossRefGoogle Scholar
  6. Borges, M., Zarbin, P. H. G, Ferreira, J. T. B., and Costa, M. L. M. 1999. Pheromone sharing: blends based on the same compounds for Euschistus heros (F.) and Piezodorus guildinii (W.) (Heteroptera: Pentatomidae). J. Chem. Ecol. 25:629–634.CrossRefGoogle Scholar
  7. Borges, M., Birkett, M., Aldrich, J., A., Oliver, J. E., Chiba, M., Murata, Y., Laumann, R. A., Barrigossi, J. A., Pickett, J. A., and Moraes, M. C. B. 2006. Sex attractant pheromone from the rice stalk stink bug, Tibraca limbativentris Stal. J. Chem. Ecol. 32:2749–2761.PubMedCrossRefGoogle Scholar
  8. Chavan, S. P., Dhondge, V. D., and Patil, S. S. 1997. Enantiospecific total synthesis of (+)-laevigatin. Tetrahedron: Asymmetry 8:2517–2518.CrossRefGoogle Scholar
  9. Corrêa-Ferreira, B. S. and Moscardi, F. 1996. Biological control of soybean stink bugs by inoculative releases of Trissolcus basalis. Entomol. Exp. Appl. 79:1–7.CrossRefGoogle Scholar
  10. Costa, M. L. M., Borges, M., and Vilela, E. F. 2000. Effect of stereoisomers of the main component of the sex pheromone of Euschistus heros (F.) (Heteroptera: Pentatomidae) in the attractiveness of female. An. Soc. Entomol. Bras. 29:413–422.CrossRefGoogle Scholar
  11. Endo, N., Wada, T., Nishiba, Y., and Sasaki, R. 2007. Interspecific pheromone cross-attraction among soybean bugs (Heteroptera): does Piezodorus hybneri (Pentatomidae) utilize the pheromone of Riptortus clavatus (Alydidae) as a kairomone? J. Chem. Ecol. 32(7):1605–1612.CrossRefGoogle Scholar
  12. Jackman, L. M. 1960. Hydrogenation–dehydrogenation reactions, pp. 329–364, in R. Raphael, E. C. Taylor, and H. Wynberg (eds.). Advances in Organic Chemistry. Methods and Results, vol. II. Interscience Publishers, New York.Google Scholar
  13. Joulain, D. and Konig, W. A. 1998. The Atlas of Spectral Data of Sesquiterpene Hydrocarbons. E.B.-Verlag, Hamburg.Google Scholar
  14. Leal, S. W., Kuwahara, X. S., Higuchi, H., Marino, C. E. B., Ono, M., and Meinwald, J. 1998. Male-released sex pheromone of the stink bug Piezodorus hybneri. J. Chem. Ecol. 24:1817–1829.CrossRefGoogle Scholar
  15. Mcbrien, H. L., Millar, J. G., Rice, R. E., Mcelfresh, J. S., Cullen, E., and Zalom, F. G. 2002. Sex attractant pheromone of the red-shouldered stink bug Thyanta pallidovirens: a pheromone blend with multiple redundant components. J. Chem. Ecol. 28:1797–1818.PubMedCrossRefGoogle Scholar
  16. Millar, J. G. 1998. Rapid and simple isolation of zingiberene from essential oils. J. Nat. Prod. 61:1025–1026.PubMedCrossRefGoogle Scholar
  17. Moraes, M. C. B., Laumann, R. A., Cokl, A., and Borges, M. 2005a. Vibratory signals of four Neotropical stink bug species. Physiol. Entomol. 30:175–188.CrossRefGoogle Scholar
  18. Moraes, M. C. B., Millar, J. G., Laumann, A. R., Sujii, E. R., Pires, C. S. S., and Borges, M. 2005b. Sex attractant pheromone from the neotropical red-shouldered stink bug, Thyanta perditor (F.). J. Chem. Ecol. 31:1415–1427.PubMedCrossRefGoogle Scholar
  19. Panizzi, A. R. and Rossi, C. E. 1991. The role of Acanthospermum hispidum in the phenology of Euschistus heros and Nezara viridula. Entomol. Exp. Appl. 59:67–74.CrossRefGoogle Scholar
  20. Shepard, M., Lawn, R. J., and Schneider, M. A. 1983. Insects on Grain Legumes in Northern Australia. A Survey of Potential Pests and Their Enemies. Univ. Queensland Press, St. Lucia, Australia.Google Scholar
  21. Singh, O. P., Singh, K. J., and Thakur, R. D. 1989. Studies on the bionomics and chemical control of stink bug, Piezodorus rubrofasciatus Fabricius, a new pest of soybean in Madhya Pradesh. Ind. J. Plant Prot. 17:81–93.Google Scholar
  22. Zarbin, H. G. P., Borges, M., Santos A. A., Oliveira, A. R. M., Simonelli, F., and Marques, F. A. 2000. Alarm pheromone system of stink bug Piezodorus guildinii (Heteroptera: Pentatomidae). J. Braz. Chem. Soc. 11:424–428.CrossRefGoogle Scholar
  23. Zhang, A., Borges, M., Aldrich, J. R., and Camp, M. J. 2003. Stimulatory bug volatiles for the neotropical brown stink bug, Euschistus heros (F.) (Heteroptera: Pentatomidae). Neotrop. Entomol. 32:713–717.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • Miguel Borges
    • 1
  • Jocelyn G. Millar
    • 2
  • R. A. Laumann
    • 1
  • Maria C. B. Moraes
    • 1
  1. 1.EMBRAPA/Recursos Genéticos e Biotecnologia/NCB-Cx.Brasília, DFBrazil
  2. 2.Department of EntomologyUniversity of CaliforniaRiversideUSA

Personalised recommendations