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.
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References
Anderson, R.F. 1948. Host selection by the pine engraver.J. Econ. Entomol. 41:596–602.
Bedard, W.D., andBrowne, L.E. 1969. A delivery-trapping system for evaluating insect chemical attractants in nature.J. Econ. Entomol. 62:1202–1203.
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.
Birch, M.C. 1978. Chemical Communication in Pine Bark Beetles.Am. Sci. 66:409–419.
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.
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.
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.
Borden, J.H. 1974. Aggregation pheromones of the Scolytidae, pp. 135–160,in M.C. Birch (ed.). Pheromones. North-Holland, Amsterdam.
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.
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.
Brownlee, R.G., andSilverstein, R.M. 1968. A micropreparative gas chromatograph and a modified carbon skeleton determinator.Anal. Chem. 40:2077–2079.
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.
Lanier, G.N., andWood, D.L. 1975. Specificity of response to pheromones in the genusIps (Coleoptera: Scolytidae).J. Chem. Ecol. 1:9–23.
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.
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.
Light, D.M., andBirch, M.C. 1979. Inhibition of the attractive pheromone response inIps paraconfusus by (R)-(−)-ipsdienol.Naturwissenschaften 66:159–160.
Mori, K. 1979. Synthesis of optically active forms of ipsdienol and ipsenol.Tetrahedron 35: 933–940.
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.
Ohloff, G., andGiersch, W. 1977. Access to optically active ipsdienol from verbenone.Helv. Chim. Acta 60:1496–1500.
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.
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.
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.
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.
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.
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.
Vité, J.P., andFrancke, W. 1976. The aggregation pheromones of bark beetles: progress and problems.Naturwissenschaften 63:550–555.
Vité, J.P., Bakke, A., andRenwick, J.A.A. 1972. Pheromones inIps (Coleoptera: Scolytidae): Occurrence and production.Can. Entomol. 104:1967–1975.
Vité, J.P., Hedden, R., andMori, K. 1976.Ips grandicollis: Field response to the optically pure pheromone.Naturwissenschaften 63:43–44.
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.
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.
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.
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.
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.
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.
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.
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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
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DOI: https://doi.org/10.1007/BF00987680