Skip to main content

Pheromone chirality of asian palm weevils,Rhynchophorus ferrugineus (Oliv.) andR. vulneratus (Panz.) (Coleoptera: Curculionidae)

Abstract

Production of 4-methyl-5-nonanol, and 4-methyl-5-nonanone by two sympatric Asian palm weevils,Rhynchophorus ferrugineus (Oliv.) andR. vulneratus (Panz.) suggested that enantiospecificity of either compound could impart species specificity of pheromone communication. Weevil-produced, racemic 4-methyl-5-nonanol and 4-methyl-5-nonanone and their stereoselectively synthesized optical isomers were subjected to gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometry (MS) on a chiral Cyclodex-B column. Only theS,S stereoisomer of 4-methyl-5-nonanol was EAD active and was produced by bothR. ferrugineus andR. vulneratus. Production and EAD activity of (S)-4-methyl-5-nonanone exceeded that of its antipode in both weevils. In field experiments in Java. (4S, 5S)-4-methyl-5-nonanol and the stereoisomeric mixture were equally attractive. The 4R,5R stereoisomer was inactive. The corresponding ketone enantiomers neither enhanced nor reduced attraction to (4S,5S)-4-methyl-5-nonanol. Lack of apparent differences betweenR. ferrugineus andR. vulneratus pheromones suggests that synonomy of both weevils should be considered unless other pre- or postzygotic reproductive isolating mechanisms are disclosed in future studies.

This is a preview of subscription content, access via your institution.

References

  1. Árn, H., Städler, E., andRauscher, S. 1975. The electroantennographic detector—a selective and sensitive tool in the gas chromatographic analysis of insect pheromones.Z. Naturforsch. 30c:722–725.

    Google Scholar 

  2. Birch, M.C., Light, D.M., andMori, K. 1977. Selective inhibition of response ofIps pini to its pheromone by theS-(—)-enantiomer of ipsenol.Nature 270:738–739.

    PubMed  Google Scholar 

  3. Birch, M.C., Light, D.L., Wood, L.E., Silverstein, R.M., Bergot, G., West, J.R., andYoung, J.C. 1980. Pheromonal attraction and allomonal interruption ofIps pini in California by the two enantiomers of ipsdienol.J. Chem. Ecol. 6:703–717.

    Google Scholar 

  4. Brown, H., Garg, C.P., andLiu, K.-L. 1971. The oxidation of secondary alcohols in diethyl ether with aqueous chromic acid. A convenient procedure for the preparation of ketones in high epimeric purity.J. Org. Chem. 36:387–390.

    Google Scholar 

  5. Camacho, A.D., Pierce, H.D., Jr., andBorden, J.H. 1993. Geometrical and optical isomerism of pheromones in two sympatricDryocoetes species (Coleoptera: Scolytidae), mediates species specificity and response level.J. Chem. Ecol. 19:2169–2182.

    Google Scholar 

  6. Enders, D., Eichenauer, H., Baus, U., Schubert, H., andKremer, K.A.M. 1984. Asymmetric synthesis via metalated chiral hydrazones. Overall enantioselective α-alkylation of acyclic ketones.Tetrahedron 40:1345–1359.

    Google Scholar 

  7. Fouquet, G., andSchlosser, M. 1974. Improved carbon-carbon linking by controlled copper catalysis.Angew. Chem. Int. Ed. 13:82–83.

    Google Scholar 

  8. Gries, G., Gries, R., Perez, A.L., Oehlschlager, A.C., Gonzalez, L.M., Pierce, H.D., Jr., Kouda-Bonafos, M., Zebeyou, M., andNanou, N. 1993. Aggregation pheromone of the African palm weevil,Rhynchophorus phoenicis (F).Naturwissenschaften 80:90–91.

    Google Scholar 

  9. Hallett, R.H., Gries, G., Gries, R., Borden, J.H., Czyzewska, E., Oehlschlager, A.C., Pierce, H.D., Jr., Angerilli, N.P.D., andRauf, A. 1993a. Aggregation pheromones of two Asian palm weevils,Rhynchophorus ferrugineus and R. vulneratus.Naturwissenschaften 80:328–331.

    Google Scholar 

  10. Hallett, R. H., Oehlschlager, A.C., Gries, G., Angerilli, N.P.D., Al Shareqi, R.K., Gassouma, M.S., andBorden, J.H. 1993b. Field testing of aggregation pheromones of two Asian palm weevils. PORIM International Palm Oil Congress, Kuala Lumpur, Malaysia, September 20–25, 1993, Proceedings. In Press.

  11. Lanier, G.N., andWood, D.L. 1975. Specificity of response to pheromones in the genusIps (Coleoptera: Scolytidae).J. Chem. Ecol. 1:9–23.

    Google Scholar 

  12. Light, D.L., andBirch, M.C. 1979. Inhibition of the attractive pheromone response inIps paraconfusus by (R)-(—)-ipsdienol.Naturwissenschaften 66:150–160.

    Google Scholar 

  13. Mori, K., Hiromasa, K., Malosse, C., andRochat, D. 1993. Synthesis of the enantiomers ofsyn-4-methyl-5-nonanol to determine the absolute configuration of the naturally occurring (4S,5S) isomer isolated as the male-produced compound ofRhynchophorus vulneratus andMetamasius hemipterus.Liebigs Ann. Chem. 1993:1201–1204.

    Google Scholar 

  14. Oehlschlager, A.C., Pierce, H.D., Jr., Morgan, B., Wimalaratne, P.D.C., Slessor, K.N., King, G.G.S., Gries, G., Gries, R., Borden, J.H., Jiron, L.J., Chinchilla, C.M., andMexzon, R.G. 1992. Chirality and field activity of rhynchophorol, the aggregation pheromone of the American palm weevil.Naturwissenschaften 79:134–135.

    Google Scholar 

  15. Oehlschlager, A.C., Chinchilla, C.M., Gonzalez, L.M., Jiron, L.F., Mexzon, R., andMorgan, B. 1993a. Development of a pheromone-based trapping system forRhynchophorus palmarum (Coleoptera: Curculionidae).J. Econ. Entomol. 86:1381–1392.

    Google Scholar 

  16. Oehlschlager, A.C., Chinchilla, C.M., andGonzalez, L.M. 1993b. Optimization of a pheromone-baited trap for the American Palm weevil. PORIM International Palm Oil Conference, Kuala Lumpur, Malaysia, September 20–25, 1993, Proceedings.In Press.

  17. Oehlschlager, A.C., Prior, R.N.B., Perez, A.L., Gries, R., Gries, G., Pierce, H.D., Jr., andLaup, S. 1995. Aggregation pheromone of the Asian palm weevil,Rhynchophorus bilineatus (Montr.), Coleoptera: Curculionidae.J. Chem. Ecol. In press.

  18. Perez, A.L., Gries, R., Gries, G., Hallett, R.H., Oehlschlager, A.C., Pierce, H.D., Jr., Gonzales, L.M., Borden, J.H., andGiblin-Davis, R.M. 1993. Pheromones ofRhynchophorus palm weevils. Paper presented at the 10th Annual ISCE Meeting, Tampa, Florida. July 31–August 4.

  19. Perez, A.L., Gries, G., Gries, R., Giblin-Davis, R.M., andOehlschlager, A.C. 1994. Pheromone chirality of African palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae).J. Chem. Ecol. 20:2653–2671.

    Google Scholar 

  20. Pierce, A.M., Borden, J.H., andOehlschlager, A.C. 1981. Olfactory response to beetle-produced volatiles and host-food attractants byOryzaephilus surinamensis andO. mercator. Can. J. Zool. 59:1980–1990.

    Google Scholar 

  21. Rochat, D.C., Malosse, C., Lettere, M., Ducrot, P.-H., Zagatti, P., Renou, M., andDescoins, C. 1991. Male-produced aggregation pheromone of the American palm weevil,Rhynchophorus palmarum L. (Coleoptera: Curculionidae): Collection, identification, electrophysiological activity and laboratory bioassay.J. Chem. Ecol. 17:2127–2141.

    Google Scholar 

  22. Rochat, D.C., Malosse, C., Lettere, M., Ramirez-Lucas, P., Einhorn, J., andZagatti, P. 1993a. Identification of new pheromone-related compounds from volatiles produced by males of four Rhynchophorinae weevils.C.R. Acad. Sci. Paris. Ser. II 316:1737–1742.

    Google Scholar 

  23. Wattanapongsiri, A. 1966. A revision of the generaRhynchophorus andDynamis (Coleoptera, Curculionidae).Dept. Agric. Sci. Bull. Bangkok 1:1–328.

    Google Scholar 

  24. Weissling, T. J., Giblin-Davis, R. M., Gries, G., Gries, R., Perez, A.L., Pierce, H.D., Jr., andOehlschlager, A.C. 1994. Aggregation pheromone of the palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae).J. Chem. Ecol. 20:505–515.

    Google Scholar 

  25. Zagatti, P., Desmier De Chenon, R., Genty, P., Rochat, D., andMariau, D. 1993. The pheromonal substances of some oil palm insect pest species: Initial studies. PORIM International Palm Oil Congress, Kuala Lumpur, Malaysia, September 20–25, 1993, Proceedings.In press.

  26. Zar, J.H. 1984. Biostatistical Analysis. Prentice-Hall, Englewood Cliffs, New Jersey.

    Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to A. Cameron Oehlschlager.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Perez, A.L., Hallett, R.H., Gries, R. et al. Pheromone chirality of asian palm weevils,Rhynchophorus ferrugineus (Oliv.) andR. vulneratus (Panz.) (Coleoptera: Curculionidae). J Chem Ecol 22, 357–368 (1996). https://doi.org/10.1007/BF02055104

Download citation

Key Words

  • Coleoptera
  • Curculionidae
  • Rhynchophorus
  • aggregation pheromone
  • pheromone chirality
  • 4-methyl-5-nonanol and 4-methyl-5-nonanone
  • Asian palm weevils