Abstract
Male potato tuberworm moths are attracted by a mixture oftrans-4,cis-7-tridecadien-1-ol acetate andtrans-4,cis-7,cis-10-tridecatrien-1-ol acetate. The synthesis of both compounds is described. Overall yields were 14.4 and 9.5% after distillation. The products were purified by liquid chromatography. Mixtures of these compounds in several ratios and quantities were tested in potato fields in Australia, Peru, and Cyprus. The largest catches were obtained from water pan traps baited with rubber sleeve stoppers containing both components in ratios varying between 1∶9 and 9∶1. The stoppers were attractive over a period of several months even under hot weather conditions.
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Adeesan, C., Tamharkar, A.J., andRahalkar, G.W. 1969. Sex pheromone gland in the potato tuberworm moth,Phthorimaea operculella:Ann. Entomol. Soc. Am. 62:670–671.
Ames, D.E., Covel, A.N., andGoodburn, T.G. 1963. Synthess of long-chain acids. Part V. Synthesis of some ω-hydroxy-actylenic acids.J. Chem. Soc. 1963:5889–5893.
Bacon, O.G., Seiber, J.N., andKennedy, G.G. 1976. Evaluation of survey trapping techniques for potato tuberworm moths with chemical baited traps.J. Econ. Entomol. 69:569–572.
Brandsma, L. 1971. Preparative Acetylenic Chemistry. Elsevier Publishing, Amsterdam. pp. 51–52.
Brown, C.A., andAhuja, V.K. 1973. “P-2” nickel catalyst with ethylenediamine, a novel system for highly stereospecific reduction of alkynes tocis-olefins.J. Chem. Soc. Chem. Commun. 1973:553–554.
Brown, C.A., andAhuja, V.K. 1973. Catalytic hydrogenation. VI. The reaction of sodium borohydride with nickel salts in ethanol solution. P-2 nickel, a highly convenient, new, selective hydrogenation catalyst with great sensitivity to substrate structure.J. Org. Chem. 38:2226–2230.
Goto, G., Masuoka, Y., andHiraga, K. 1974. Photooxidation of the sex pheromone (Z,E)-9, 12-tetradecadienyl-1-acetate.Chem. Lett. 1974:1275–1278.
Henrick, C.A. 1977. The synthesis of insect sex pheromones.Tetrahedron 33:1845–1889.
Houx, N.W.H., andVoerman, S. 1976. High-performance liquid chromatography of potential insect sex attractants and other geometrical isomers on a silver-loaded ion exchanger.J. Chromatogr. 129:456–459.
Houx, N.W.H., Voerman, S., andJongen, W.M.F. 1974. Purification and analysis of synthetic insect sex attractants by liquid chromatography on a silver-loaded resin.J. Chromatogr. 96:25–32.
Kennedy, J.S. 1977. Behaviorally discriminating assays of attractants and repellents, pp. 215–229,in H.H. Shorey and J.J. McKelvey, Jr. (eds.). Chemical Control of Insect Behavior: Theory and Application. John Wiley and Sons, New York.
Kraevskii, A.A., Fedorova, N.V., Zotova, S.A., Sarycheva, I.K., andPreobrazhenskii, N.A. 1964. Polyynic compounds with a central methylene group, synthesis of heptadiyn-1,4 and undecatriyn-2,5,8-ol-1.J. Gen. Chem. U.S.S.R. 34:553–555.
Persoons, C.J., Voerman, S., Verwiel, P.E.J., Nooijen, P.J.F., Nooijen, W.J., Ritter, F.J., andMinks, A.K. 1976. Sex pheromone of the potato tuberworm moth,Phthorimaea operculella: Isolation and identification.Med. Fac. Landbouwwet. Rijksuniv. Gent. 41:945–948.
Persoons, C.J., Voerman, S., Verwiel, P.E.J., Ritter, F.J., Nooijen, W.J., andMinks, A.K. 1976. Sex pheromone of the potato tuberworm moth,Phthorimaea operculella: Isolation, identification and field evaluation.Entomol. Exp. Appl. 20:289–300.
Raphael, R.A. 1955. Acetylenic Compounds in Organic Synthesis. Butterworth, London, p. 202.
Roelofs, W.L., Kochansky, J.P., Cardé, R.T., Kennedy, G.G., Henrick, C.A., Labovitz, J.N., andCorbin, V.L. 1975. Sex pheromone of the potato tuberworm moth,Phthorimaea operculella.Life Sci. 17:699–706.
Stork, G., Grieco, P.A., andGregson, M. 1969. Synthesis of allylic halides and 1,5-dienes from allylic alcohols.Tetrahedron Lett. 18:1393–1395.
Voerman, S., Minks, A.K., andPersoons, C.J. 1977. Elucidation of the sex pheromone system of the potato tuberworm moth,Phthorimaea operculella (Zeller) (Lepidoptera, Gelechiidae): A short review.Potato Res. 20:123–126.
Yamaoka, R., Fukami, H., andIshii, S. 1976. Isolation and identification of the female sex pheromone of the potato tuberworm moth,Phthorimaea operculella (Zeller):Agric. Biol. Chem. 40:1971–1977.
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Voerman, S., Rothschild, G.H.L. Synthesis of the two components of the sex pheromone system of the potato tuberworm moth,Phthorimaea operculella (Zeller) (Lepidoptera: Gelechiidae) and field experience with them. J Chem Ecol 4, 531–542 (1978). https://doi.org/10.1007/BF00988917
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DOI: https://doi.org/10.1007/BF00988917