Abstract
1-Methylcyclohex-2-en-1-ol (1,2-MCH-ol) was synthesized, identified as a compound found in volatiles of the female Douglas-fir beetle, and shown by bioassays to be an aggregation pheromone. 1,2-MCH-ol matches in both GC retention index and mass spectrum a compound released by the female after feeding. 3,3-MCH-ol was also synthesized as a candidate compound; its mass spectrum is presented because published mass spectra are incorrect for this compound. Synthetic 1,2-MCH-ol increased arrestment and stridulation of males in olfactory walkways and increased trap catches of flying beetles. Males were more responsive to 1,2-MCH-ol than females.
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Bedard, W.D., Tilden, P.E., Wood, D.L., Silverstein, R.M., Brownlee, R.G., andRodin, J.O. 1969. Western pine beetle: field response to its sex pheromone and a synergistic host terpene, myrcene.Science 164:1284–1285.
Budde, W.L., andEichelberger, J.W. 1979. Organics Analysis Using Gas Chromatography Mass Spectrometry-A Technique and Procedures Manual. Ann Arbor Science Publishers, Ann Arbor, Michigan.
Dickens, J.C.,Gutmann, A.,Payne, T.L.,Ryker, L.C., andRudinsky, J.A. 1983. Antennal olfactory responsiveness of the Douglas-fir beetle,Dendroctonus pseudotsugae Hopkins (Coleoptera: Scolytidae) to pheromones and host odors.J. Chem. Ecol. In press.
Furniss, M.M., andSchmitz, R.F. 1971. Comparative attraction of Douglas-fir beetles to frontalin and tree volatiles. USDA For. Serv. Res. Pap. INT-96, 16 pp.
Furniss, M.M., Daterman, G.E., Kline, L.N., Mcgregor, M.D., Trostle, G.C., Pettinger, L.F., andRudinsky, J.A. 1974. Effectiveness of the Douglas-fir beetle antiaggregative pheromone methylcyclohexenone at three concentrations and spacings around felled host trees.Can. Emomol. 106:381–392.
Heller, S.R., andMilne, G.W.A., 1978. EPA/NIH Mass spectral Data Base. U.S. Govt. Printing Office, Washington, D.C.
Jantz, O.K., andJohnsey, R.L. 1964. Determination of sex of the Douglas-fir beetleDendroctonus pseudotsugae Hopkins (Coleoptera: Scolytidae).Can. Entomol 96:1327–1329.
Jantz, O.K., andRudinsky, J.A. 1965. Laboratory and field methods for assaying olfactory responses of the Douglas-fir beetle,Dendroctonus pseudotsugae Hopkins.Can. Entomol. 97:935–941.
Meinwald, J., andHendry, L. 1971. The deconjugation of isophorone.J. Org. Chem. 36:1446–1447.
Renwick, J.A.A., andHughes, P.R. 1975. Oxidation of unsaturated cyclic hydrocarbons byDendroctonus frontalis.Insect Biochem. 5:459–463.
Rudinsky, J.A., andMichael, R.R. 1972. Sound production in Scolytidae: Chemostimulus of sonic signal by the Douglas-fir beetle.Science 175:1386–1390.
Rudinsky, J.A., andRyker, L.C. 1976. Sound production in Scolytidae: Rivalryand premating stridulation of male Douglas-fir beetle.J. Insect Physiol. 22:997–1003.
Rudinsky, J.A., andRyker, L.C. 1980. Multifunctionality of Douglas-fir beetle pheromone 3,2-MCH confirmed with solvent dibutyl phthalate.J. Chem. Ecol. 6:193–201.
Rudinsky, J. A., Morgan, M.E., Libbey, L.M., andPutnam, T.B. 1974. Additional components of the Douglas-fir beetle (Col., Scolytidae) aggregative pheromone and their possible utility in pest control.Z. Angew. Enlomol. 76:65–77.
Ryker, L.C., Libbey, L.M., andRudinsky, J. A. 1979. Comparison of volatile compounds and stridulation emitted by the Douglas-fir beetle from Idaho and Western Oregon populations.Environ. Entomol. 8:789–798.
Snedecor, G.W., andCochran, W.G. 1967. Statistical Methods. Iowa State University Press, Ames. 593 pp.
Stenhagen, E., Abrahamsson, S., andMclafferty, F.W. 1974. Registry of Mass Spectral Data. Wiley & Sons, New York.
Van Den Dool, H., andKratz, P.D. 1963. A generalization of theTetention index system including linear temperature-programmed gas-liquid partition chromatography.J. Chromalogr. 11:463–471.
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Coleoptera: Scolytidae.
Research supported by NSF grant PCN 79-21708 to Oregon State University, OSU Agric. Exp. Sta. Tech. Paper No. 6507.
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Libbey, L.M., Oehlschlager, A.C. & Ryker, L.C. 1-Methylcyclohex-2-en-1-ol as an aggregation pheromone ofDendroctonus pseudotsugae . J Chem Ecol 9, 1533–1541 (1983). https://doi.org/10.1007/BF00988419
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DOI: https://doi.org/10.1007/BF00988419