Skip to main content
SpringerLink
Log in

Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

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

Abstract

There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil,Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil,Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-4-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by maleR. phoenicis and maleR. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, withR. phoenicis in Côte d'Ivoire andR. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Arn, 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.

    CAS  Google Scholar 

  • Bestmann, H.J., andVostrowsky, O. 1988. Pheromones of the Coleoptera, pp. 93–183,in E.D. Morgan and N.B. Mandava (eds.). CRC Handbook of Natural Pesticides, Vol. IV, Pheromones Part A. CRC Press, Boca Raton, Florida.

    Google Scholar 

  • Birch, M.C. 1984. Aggregation in bark beetles, pp. 331–353,in W.J. Bell and R.T. Cardé (eds.). Chemical Ecology of Insects. Chapman and Hall, London.

    Google Scholar 

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

    Article  CAS  Google Scholar 

  • Blight, M.M., Mellon, F.A., Wadhams, L.J., andWenham, M.J. 1977. Volatiles associated withScolytus scolytus beetles on English elm.Experientia 33:845–846.

    Article  CAS  Google Scholar 

  • Blight, M.M., Wadhams, L.J., andWenham, M.J. 1978. Volatiles associated with unmatedScolytus scolytus beetles on English elm: Differential production of α-multistriatin and 4-methyl-3-heptanol, and their activities in a laboratory bioassay.Insect Biochem. 8:135–142.

    Article  CAS  Google Scholar 

  • Blight, M.M., Wadhams, L.J., andWenham, M.J. 1979. The stereoisomeric composition of the 4-methyl-3-heptanol produced byScolytus scolytus and the preparation and biological activity of the four synthetic stereoisomers.Insect Biochem. 9:525–533.

    Article  CAS  Google Scholar 

  • Borden, J.H. 1985. Aggregation pheromones, pp. 257–285,in G.A. Kerkut and L.I. Gilbert (eds.). Comprehensive Insect Physiology, Biochemistry and Pharmacology, Vol. 9. Pergamon Press, Oxford.

    Google Scholar 

  • Borden, J.H., Chong, L., McLean, J.A., Slessor, K.N., andMori, K. 1976.Gnathotrichus sulcatus: Synergistic response to enantiomers of the aggregation pheromone sulcatol.Science 192:894–896.

    PubMed  CAS  Google Scholar 

  • Borden, J.H., Handley, J.R., McLean, J.A., Silverstein, R.M., Chong, L., Slessor, K.N., Johnston, B.D., andSchuler, H.R. 1980. Enantiomer-based specificity in pheromone communication by two sympatricGnathotrichus species (Coleoptera: Scolytidae).J. Chem. Ecol. 6:445–455.

    Article  Google Scholar 

  • Brand, J.M., Young, J.C., andSilverstein, R.M. 1979. Insect pheromones: A critical review of recent advances in their chemistry, biology, and application.Fortschr. Chem. Org. Naturst. 37:1–190.

    PubMed  CAS  Google Scholar 

  • Brandsma, L. 1988. Preparative Acetylenic Chemistry. Elsevier, Amsterdam. pp. 283–284.

    Google Scholar 

  • Byers, J.A. 1989. Chemical ecology of bark beetles.Experientia 45:271–283.

    Article  CAS  Google Scholar 

  • Dai, L.-X., Bo, I. andZhang, Y.-Z. 1988. A simple, divergent, asymmetric synthesis of all members of the 2,3,6-trideoxy-3-aminohexose family.J. Am. Chem. Soc. 110:5195–5196.

    Article  CAS  Google Scholar 

  • Dyer, U.C., andKishi, Y. 1988. Synthesis of C-sucrose.J. Org. Chem. 53:3383–3384.

    Article  CAS  Google Scholar 

  • Evershed, R.P. 1988. Insect olfaction and molecular structure, pp. 1–33,in E.D. Morgan and N.B. Mandava (eds.). CRC Handbook of Natural Pesticides, Vol. IV, Pheromones Part A. CRC Press, Boca Raton, Florida.

    Google Scholar 

  • Gao, Y., Hanson, R.M., Klunder, J.M., Ko, S.Y., Masamune, H., andSharpless, K.B. 1987. Catalytic asymmetric epoxidation and kinetic resolution: Modified procedures including in situ derivatization.J. Am. Chem. Soc. 109:5765–5780.

    Article  CAS  Google Scholar 

  • Gries, G., Gries, R., Perez, A.L., Gonzales, L.M., Pierce, H.D., Jr., Oehlschlager, A.C., Rhainds, M., Zebeyou, M., andKouame, B. 1994. Ethyl propionate: Synergistic kairomone for African palm weevil,Rhynchophorus phoenicis L. (Coleoptera: Curculionidae).J. Chem. Ecol. 20:889–897.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • Hill, G., Sharpless, K.B., Exon, C., andRegenye, R. 1985. Enantioselective epoxidation of allylic alcohols: (2S,3S)-3-Propyloxiranemethanol (oxiranemethanol, 3-propyl-, (2S,3S)-).Org. Synth. 63:66–78.

    CAS  Google Scholar 

  • Hughes, D.L. 1992. The Mitsunobu reaction.Org. React. 42:335–656.

    CAS  Google Scholar 

  • Leal, W.S., andMochizuki, F. 1993. Sex pheromone reception in the scarab beetleAnomala cuprea. Enantiomeric discrimination by sensilla placodea.Naturwissenschaften 80:278–281.

    Article  CAS  Google Scholar 

  • Mitsunobu, O. 1981. The use of diethyl azocarboxylate and triphenylphosphine in synthesis and transformation of natural products.Synthesis 1981:1–28.

  • Miyashita, M., Toshimitsu, Y., Siratani, T., andIrie, H. 1993. Enantioselective synthesis of (−)-serricornin, a sex pheromone of a female cigarette beetle (Lasioderma serricone F.).Tetrahedron Asymm. 4:1573–1578.

    Article  CAS  Google Scholar 

  • Mori, K., andBrevet, J.-L. 1991. Pheromone synthesis: CXXXIII. Synthesis of both the enantiomers of (3Z,9Z)-cis-6,7-epoxy-3,9-nonadecadiene, a pheromone component ofEranis defoliaria.Synthesis 1991:1125–1129.

  • Mori, K., andHarashima, S. 1993. Synthesis of (2E,4E,6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (matsuone)—the primary component of the sex pheromone of the threeMatsucoccus pine bast scales-and its antipode.Liebigs Ann. Chem. 1993:993–1001.

    Google Scholar 

  • Mori, K., Kiyota, H., andRochat, D. 1993. Synthesis of the stereoisomers of 3-methyl-4-octanol to determine the absolute configuration of the naturally occurring (3S,4S)-isomer isolated as the male-produced aggregation pheromone of the African palm weevil,Rynchophorus phoenicis.Liebigs Ann. Chem. 1993:865–870.

    Google Scholar 

  • Nakagawa, N., andMori, K. 1984. Synthesis of (3S,4S)-4-methyl-3-heptanol and its (3S,4R)-isomer employing asymmetric epoxidation coupled with regioselective cleavage of epoxides with trimethylaluminum.Agric. Biol. Chem. 48:2505–2510.

    CAS  Google Scholar 

  • Oehlschlager, A.C., King, G.G.S., Pierce, H.D., Jr., Pierce, A.M., Slessor, K.N., Millar, J.G., andBorden, J.H. 1987. Chirality of macrolides pheromones of grain beetles in the generaOryzaephilus andCryptolestes and its implications for species specificity.J. Chem. Ecol. 13:1543–1554.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

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

    Google Scholar 

  • Oehlschlager, A.C., Prior, R.N.B., Perez, A.L., Pierce, H.D., Jr., Gries, R., andGries, G. 1994. Structure, chirality and field testing of male-produced aggregation pheromone for the Asian palm weevil,Rhynchophorus bilineatus (Montr.), (Coleoptera, Curculionidae).J. Chem. Ecol. Submitted.

  • Paquette, L.A., andSugimura, T. 1986. Enantiospecific total synthesis and absolute configurational assignment of (-)-puntactin A (antibiotic M95464).J. Am. Chem. Soc. 108:3841–3842.

    Article  CAS  Google Scholar 

  • Payne, T.L., Richerson, J.V., Dickens, J.C., West, J.R., Mori, K., Berisford, C.W., Hedden, R.L., Vité, J.P., andBlum, M.S. 1982. Southern pine beetle: Olfactory receptor and behavior discrimination of enantiomers of the attractant pheromone frontalin.J. Chem. Ecol. 8:873–881.

    Article  CAS  Google Scholar 

  • Pearce, G.T., Gore, W.E., Silverstein, R.M., Peacock, J.W., Cuthbert, R.A., Lanier, G.N., andSimeone, J.B. 1975. Chemical attractants for the smaller European elm bark beetleScolytus multistriatus (Coleoptera: Scolytidae).J. Chem. Ecol. 1:115–124.

    Article  CAS  Google Scholar 

  • 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. 10th Annual ISCE Meeting, Tampa, Florida. July 31–August 4.

  • Pfaltz, A., andMattenberger, A. 1982. Regioselective opening ofβ-alkoxyepoxides with trimethylaluminum.Angew. Chem. Int. Ed. Engl. 21:71–72.

    Article  Google Scholar 

  • Pierce, A.M., Pierce, H.D., Jr, Oehlschlager, A.C., andBorden, J.H. 1987. Response ofOryzaephilus surinamensis andO. mercator to the chiral isomers of their macrolide aggregation pheromones.J. Chem. Ecol. 13:1525–1542.

    Article  CAS  Google Scholar 

  • Rochat, D., 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.

    Article  CAS  Google Scholar 

  • Rochat, D., Descoins, C., Malosse, C., Nagnan, P., Zagatti, P., Akamou, F., andMariau, D. 1993. Ecologie chimique des charançons des palmiers,Rhynchophorus spp. (Coleoptera).Oleagineux 48:225–236.

    CAS  Google Scholar 

  • SAS Institute. 1990. SAS System for Personal Computers, Release 6.04. SAS Institute Inc., Cary, North Carolina.

    Google Scholar 

  • Slessor, K.N., King, G.G.S., Miller, D.R., Winston, M.L., andCuforth, T.L. 1985. Determination of chirality of alcohol or latent alcohol semiochemicals in individual insects.J. Chem. Ecol. 11:1659–1667.

    Article  CAS  Google Scholar 

  • Still, W.C., Kahn, M., andMitra, A. 1978. Rapid chromatographic technique for preparative separations with moderate resolution.J. Org. Chem. 43:2923–2925.

    Article  CAS  Google Scholar 

  • Suzuki, T., Saimoto, H., Tomioka, H., Oshima, K., andNozaki, H. 1982. Regio- and stereoselective ring opening of epoxy alcohols with organoaluminum compounds leading to 1,2-diols.Tetrahedron Lett. 23:3597–3600.

    Article  CAS  Google Scholar 

  • Takano, S., Yanase, M., andOgasawacra, K. 1989. Nucleophilic cleavage of (2S,3S)-3-phenylglycidol.Heterocycles 29:249–252.

    Article  CAS  Google Scholar 

  • Tumlinson, J.H., Klein, M.G., Doolittle, R.E., Ladd, T.L., andProveaux, A.T. 1977. Identification of the female Japanese beetle sex pheromone: Inhibition of male response by an enantiomer.Science 197:789–792.

    PubMed  CAS  Google Scholar 

  • Vaccaro, H.A., Levy, D.E., Sawabe, A., Jaetsch, T., andMasamune, S. 1992. Towards the synthesis of calyculin: A synthetic intermediate corresponding to the C(26)-C(37) fragment.Tetrahedron Lett. 33:1937–1940.

    Article  CAS  Google Scholar 

  • Vité, J.P., Billing, R.F., Ware, C.W., andMori, K. 1985. Southern pine beetle: Enhancement or inhibition of aggregation response mediated by enantiomers ofendo-brevicomin.Naturwissenschaften 72:99–100.

    Article  Google Scholar 

  • Wadhams, L.J., Angst, M.E., andBlight, M.M. 1982. Responses of the olfactory receptors ofScolytus scolytus (F.) (Coleoptera: Scolytidae) to the stereoisomers of 4-methyl-3-heptanol.J. Chem. Ecol. 8:477–492.

    Article  CAS  Google Scholar 

  • 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,Rynchophorus cruentatus (F.) (Coleoptera: Curculionidae).J. Chem. Ecol. 20:505–515.

    Article  CAS  Google Scholar 

  • Zar, J.H. 1984. Biostatistical Analysis. Prentice-Hall, Englewood Cliffs, New Jersey. 718 pp.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Simon Fraser University, V5A 1S6, Burnaby, British Columbia, Canada

    Alice L. Perez & A. Cameron Oehlschlager

  2. Centre for Pest Management, Department of Biological Sciences, Simon Fraser University, V5A 1S6, Burnaby, British Columbia, Canada

    Gerhard Gries & Regine Gries

  3. Institute of Food and Agricultural Sciences Fort Lauderdale Research and Education Centre, University of Florida, 3314, Fort Lauderdale, Florida

    Robin M. Giblin-Davis

Authors
  1. Alice L. Perez
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gerhard Gries
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Regine Gries
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Robin M. Giblin-Davis
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. Cameron Oehlschlager
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Perez, A.L., Gries, G., Gries, R. et al. Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae). J Chem Ecol 20, 2653–2671 (1994). https://doi.org/10.1007/BF02036199

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02036199

Key words

Search

Navigation