Abstract
A short synthesis of (E, Z)-7,9-dodecadien-1-yl acetate from propargyl alcohol and 6-bromohexanol via acetylenic-allenic isomerization of the resulting bis-THP-1,9-non-2-yn-diol is described. The field test of several preparations showed that theE,E isomer does not interfere with the biological activity of the pheromone. It was found that the “crude” preparation has higher activity than purified pheromone or virgin females.
Similar content being viewed by others
References
Bestmann, H.J., Süb, J., andVostrovsky, O. 1979 Synthese der sexuallockstoffe (E)-7, (Z)-9-dodecadienylacetat, (E)-9,11-dodecadienylacetat und (Z)-9,(E)-11-tetradecadienylacetat.Tetrahedron Lett. 1979:2467–2470.
Bestmann, H.J., andVostrovsky, O. 1979. Synthesis of pheromones by stereoselective carbonyl olefination: a unitised construction principle.Chem. Phys. Lipids 24:335–389.
Cassani, G., Massardo, P., andPiccardi, P. 1980. Synthesis ofLobesia botrana andSpodoptera littoralis natural sex-attractant.Tetrahedron Lett. 21:3497–3498.
Descoins, C., Lalanne-Cassou, B., andSamain, D. 1974. Sur des attractifs sexuels synthétiques pour l'Eudemis de la VigneLobesia botrana (Schiff).C.R. Acad. Sci. Ser. D. 279:907–910.
Descoins, C., Samain, D., Lalanne-Cassou, B., andGallois, M. 1977. Synthèses stéréo-selectives des acetoxy-1 dodecadienes 7E, 9E et 7E, 9Z, attractifs sexuels pour le mále de L'Eudemis de la vigne:Lobesia botrana.Bull. Soc. Chim. Fr. 1977:941–946.
Dressaire, G., andLanglois, Y. 1980. Pyridines as precursors of conjugated diene pheromones (II). Stereoselective synthesis of (7E,9Z)-dodecadien-1-yl acetate, sex pheromoneof Lobesia botrana.Tetrahedron Lett. 21:67–70.
Glass, E.H., Roelofs, W.L., Arn, H., andComeau, A. 1970. Sex pheromone trapping of the red-banded leaf roller moth and development of a long-lasting polyethylene wick.J. Econ. Entomol. 63:370–373.
Gurevitz, E., andGothilf, S., 1981. Mass trapping of male grapevine mothLobesia botrana Schiff, in vineyards.Alon Hanotea In press (in Hebrew).
Henrick, C.A. 1977. The synthesis of insect sex pheromones.Tetrahedron 33:1845–1889.
Labovitz, J.N., Henrick, C.A., andCorbin, V.L. 1975. Synthesis of (7E,9Z)-7,9-dodecadien-1-yl acetate, a sex pheromone ofLobesia botrana.Tetrahedron Lett. 1975:4209–4212.
Negishi, E., andAbramovitch, A. 1977. A highly efficient chemo-regio-, and stereoselective synthesis of (7E,9Z)-dodecadien-1-yl acetate, a sex pheromone ofLobesia botrana, via a functionalized organoborate.Tetrahedron Lett. 1977:411–414.
Nesbitt, B.F., Beevor, P.S., Hall, D.R., Lester, R., Sternlicht, M. andGoldenberg, S. 1977. Identification and synthesis of the female sex pheromone of the citrus flower moth (Prays citri).Insect Biochem. 7:355–359.
Roehrich, R., Carles, J.P., Tresor, C., andDe Vathaire, M. 1979. Essais de “confusion sexuelle” contre les tordeuses de la grappe l'EudemisLobesia botrana Den et Schiff, et la CochylisEitpoecilia ambiguella Tr.Ann. Zool. Ecol. Anim. 11:659–675.
Roelofs, W., Kochansky, J., Carde, R., Arn, H., andRauscher, S. 1973. Sex attractant of the grape vine mothLobesia botrana Schweiz.Entomon. Ges. 46:71–73.
Roelofs, W.,Kochansky, J., andCardé, R. 1975.Trans-7-cis-9-Dodecadien-1-yl acetate.Chem. Abstr. 82:111610m, U.S. patent 3,845,108.
Schwartz, M., andWaters, R.M. 1972. Insect sex pheromones XII. An efficient procedure for the preparation of unsaturated alcohols and acetates.Synthesis 1972:567–568.
Teich, I., Neumark, S., Jacobson, M., Klug, J.T., Shani, A., andWaters, R.M. 1979. Mass trapping of males of Egyptian cotton leafworm (Spodoptera littoralis) and large-scale synthesis of prodlure, pp. 343–350,in F.J. Ritter (ed.). Chemical Ecology: Odour Communication in Animals. Elsevier North Holland Biomedical Press, Amsterdam.
Waters, R.M., Voaden, D.J., Shani, A., andKlug, J.T. 1978. The preparation of (E)-2-pentenal.Org. Prep. Proc., Int. 10:1–4.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Ideses, R., Klug, J.T., Shani, A. et al. Sex pheromone of the European grapevine moth,Lobesia botrana Schiff. (Lepidoptera: Tortricidae): Synthesis and effect of isomeric purity on biological activity. J Chem Ecol 8, 195–200 (1982). https://doi.org/10.1007/BF00984016
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00984016