Skip to main content
Log in

Pheromonal attraction and allomonal interruption ofIps pini in California by the two enantiomers of ipsdienol

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

Abstract

Air containing volatile compounds from around maleIps pini boring in ponderosa pine logs from California was condensed, fractionated by GC, and assayed in the laboratory and field. The only fraction that showed consistent activity in laboratory assays contained a single compound identified as ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol). Synthetic racemic ipsdienol showed no activity in either the laboratory or field. However, (−)-ipsdienol, the naturally occurring enantiomer, was attractive toI. pini in the laboratory and field, whereas (+)-ipsdienol interrupted the response ofI. pini to a natural source of attraction in field tests. (−)-Ipsdienol is a major component of the attractant pheromone of this species, since its level of activity in laboratory assays was quantitatively comparable to that of the condensed volatiles, and it was as attractive as maleI. pini boring in ponderosa pine in the field. (+)-Ipsdienol is a component of the pheromone of the competing species,I. paraconfusus.

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

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /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.

Similar content being viewed by others

References

  • Anderson, R.F. 1948. Host selection by the pine engraver.J. Econ. Entomol. 41:596–602.

    Google Scholar 

  • Bedard, W.D., andBrowne, L.E. 1969. A delivery-trapping system for evaluating insect chemical attractants in nature.J. Econ. Entomol. 62:1202–1203.

    Google Scholar 

  • Bergot, B.J., Anderson, R.J., Schooley, D.A., andHenrick, C.A. 1978. Liquid chromatographic analysis of enantiomeric purity of several terpenoid acids as their (1-(1-naphthyl) ethylamide derivatives.J. Chromatogr. 155:97–105.

    Google Scholar 

  • Birch, M.C. 1978. Chemical Communication in Pine Bark Beetles.Am. Sci. 66:409–419.

    Google Scholar 

  • Birch, M.C., andLight, D.M. 1977. Inhibition of the attractant pheromone response inIps pini andI. paraconfusus (Coleoptera: Scolytidae): Field evaluation of ipsenol and linalool.J. Chem. Ecol. 3:257–267.

    Google Scholar 

  • Birch, M.C., andWood, D.L. 1975. Mutual inhibition of the attractant pheromone response by two species ofIps (Coleoptera: Scolytidae).J. Chem. Ecol. 1:101–113.

    Google Scholar 

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

    Google Scholar 

  • Borden, J.H. 1974. Aggregation pheromones of the Scolytidae, pp. 135–160,in M.C. Birch (ed.). Pheromones. North-Holland, Amsterdam.

    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  Google Scholar 

  • Browne, L.E., Birch, M.C., andWood, D.L. 1974. Novel trapping and delivery systems for airborne insect pheromones.J. Insect Physiol 20:183–193.

    Google Scholar 

  • Brownlee, R.G., andSilverstein, R.M. 1968. A micropreparative gas chromatograph and a modified carbon skeleton determinator.Anal. Chem. 40:2077–2079.

    Google Scholar 

  • Fish, R.H., Browne, L.E., Wood, D.L., andHendry, L.B. 1979. Pheromone biosynthetic pathways: Conversions of deuterium labelled ipsdienol with sexual and enantioselectivity inIps paraconfusus Lanier.Tetrahedron Lett. 17:1465–1468.

    Google Scholar 

  • 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 

  • Lanier, G.N., Birch, M.C., Schmitz, R.F., andFurniss, M.M. 1972. Pheromones ofIps pini (Coleoptera: Scolytidae): variation in response among three population.Can. Entomol. 104: 1917–1923.

    Google Scholar 

  • Lanier, G.N., Claesson, A., Stewart, T., Piston, J.J., andSilverstein, R.M. 1980.Ips pini: The basis for interpopulational differences in pheromone biology.J. Chem. Ecol. 6:677–687.

    Google Scholar 

  • Light, D.M., andBirch, M.C. 1979. Inhibition of the attractive pheromone response inIps paraconfusus by (R)-(−)-ipsdienol.Naturwissenschaften 66:159–160.

    Google Scholar 

  • Mori, K. 1979. Synthesis of optically active forms of ipsdienol and ipsenol.Tetrahedron 35: 933–940.

    Google Scholar 

  • Mustaparta, H., Angst, M.E., andLanier, G.N. 1980. Receptor discrimination of enantiomers of the aggregation pheromone ipsdienol in two speciesof Ips.J. Chem. Ecol. 6:689–701.

    Google Scholar 

  • Ohloff, G., andGiersch, W. 1977. Access to optically active ipsdienol from verbenone.Helv. Chim. Acta 60:1496–1500.

    Google Scholar 

  • Plummer, E.L., Stewart, T.E., Byrne, K., Pearce, G.T., andSilverstein, R.M. 1976. Determination of the enantiomeric composition of several insect pheromone alcohols.J. Chem. Ecol. 2:307–331.

    Google Scholar 

  • Silverstein, R.M. 1979. Enantiomeric composition and bioactivity of chiral semiochemicals in insects, pp. 133–146,in F.J. Ritter (ed.). Chemical Ecology: Odour Communication in Animals. North-Holland, Amsterdam.

    Google Scholar 

  • Silverstein, R.M., andYoung, J.C. 1976. Insects generally use multicomponent pheromones, pp. 1–23,in M. Beroza (ed.). Pest Management with Insect Sex Attractants. A.C.S. Symposium Series 23.

  • Silverstein, R.M., Rodin, J.O., andWood, D.L. 1966a. Sex attractants in the frass produced by maleIps confusus in ponderosa pine.Science 154:509–510.

    Google Scholar 

  • Silverstein, R.M., Rodin, J.O., Wood, D.L., andBrowne, L.E. 1966b. Identification of two new terpene alcohols from frass produced byIps confusus in ponderosa pine.Tetrahedron 22:1929–1936.

    Google Scholar 

  • Stewart, T.E. 1975. Volatiles isolated fromIps pini: Isolation, identification, enantiomeric composition, biological activity. M.S. thesis. College of Environmental Science and Forestry, SUNY, Syracuse, 135 pp.

    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.

    Google Scholar 

  • Vité, J.P., andFrancke, W. 1976. The aggregation pheromones of bark beetles: progress and problems.Naturwissenschaften 63:550–555.

    Google Scholar 

  • Vité, J.P., Bakke, A., andRenwick, J.A.A. 1972. Pheromones inIps (Coleoptera: Scolytidae): Occurrence and production.Can. Entomol. 104:1967–1975.

    Google Scholar 

  • Vité, J.P., Hedden, R., andMori, K. 1976.Ips grandicollis: Field response to the optically pure pheromone.Naturwissenschaften 63:43–44.

    PubMed  Google Scholar 

  • Wood, D.L. 1970. Pheromones of bark beetles, pp. 301–316,in: D.L. Wood, R.M. Silverstein, and M. Nakajima (eds.). Control of Insect Behavior of Natural Products, Academic Press, New York.

    Google Scholar 

  • Wood, D.L. 1977. Manipulation of forest insect pests, pp. 369–384,in H.H. Shorey and J.J. McKelvey, Jr. (eds.). Chemical Control of Insect Behavior. Wiley, New York.

    Google Scholar 

  • Wood, D.L., Browne, L.E., Silverstein, R.M., andRodin, J.O. 1966. Sex pheromones of bark beetles—I. Mass production, bio-assay, and isolation of the sex pheromone ofIps confusus (LeC.).J. Insect Physiol. 12:523–536.

    PubMed  Google Scholar 

  • Wood, D.L., Stark, R.W., Silverstein, R.M., andRodin, J.O. 1967. Unique synergistic effects produced by the principal sex attractant compounds ofIps confusus (LeConte) (Coleoptera: Scolytidae).Nature 215:206.

    Google Scholar 

  • Wood, D.L., Browne, L.E., Bedard, W.D., Tilden, P.E., Silverstein, R.M., andRodin, J.O. 1968. Response ofIps confusus to synthetic sex pheromones in nature.Science 159:1373–1374.

    PubMed  Google Scholar 

  • Wood, D.L., Browne, L.E., Ewing, B., Lindahl, K., Bedard, W.D., Tilden, P.E., Mori, K., Pitman, G.B., andHughes, P.R. 1976. Western pine beetle: specificity among enantiomers of male and female components of an attractant pheromone.Science 192:896–898.

    PubMed  Google Scholar 

  • Young, J.C., Brownlee, R.G., Rodin, J.O., Hildebrand, D.N., Silverstein, R.M., Wood, D.L., Birch, M.C., andBrowne, L.E. 1973. Identification of linalool produced by two species of bark beetles of the genusIps.J. Insect Physiol. 19:1615–1622.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

(C.B.R.I. Contribution No. 1043.)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Birch, M.C., Light, D.M., Wood, D.L. et al. Pheromonal attraction and allomonal interruption ofIps pini in California by the two enantiomers of ipsdienol. J Chem Ecol 6, 703–717 (1980). https://doi.org/10.1007/BF00987680

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00987680

Key words

Navigation