Abstract
Photo- and radical isomerization of (E, Z)-7,9-dodecadien-1-yl acetate (DDA) leads to an equilibrium mixture of all four possible geometric isomers of 7,9-DDA in the ratio ofE,E, 69–76%;Z,E, 11–13%;E, Z, 12–15%; andZ, Z, 1–3%. Iodine catalysis of the isomerization takes place even in dark at room temperature and is probably a radical reaction.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Benesi, H.A., andHildebrand, J.H. 1949. A spectroscopic investigation of the interaction of iodine with aromatic hydrocarbon.J. Am. Chem. Soc. 71:2703–2707.
Buser, H.R., Rauscher, S., andArn, H. 1974. Sex pheromone ofLobesia botrana: (E,Z)-7,9-Dodecadienyl acetate in the female grape vine moth.Z. Naturforsch. 29c:781–783.
Hall, D.R., Beevor, P.S., Lester, R., andNesbitt, B.F. 1980. (E, E)-10,12-Hexadecadienal: a component of the female sex pheromone of the spiny bollworm (Earias insulana).Experientia 36:152–153.
Ideses, R.,Shani, A., andKlug, J. T. 1982a. Cyclic peroxide-an isolable intermediate in singlet oxygen oxidation of pheromones to furan system. Submitted for publication.
Ideses, R., Klug, J.T., Shani, A., Gothlif, S., andGurevitz, E. 1982b. Sex pheromone of the European grapevine moth (Lobesia botrana): Synthesis and the effect of isomeric purity on the biological activity.J. Chem. Ecol. 8:195–200.
March, J. 1977. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 2nd ed. McGraw-Hill, New York, pp. 28,635.
Roelofs, W., Kochansky, J., Carde, R., Arn, H., andRauscher, S. 1973. Sex attractant of the grape vine moth,Lobesia botrana.Mitt. Schweiz. Entomol. Ges. 46:71–73.
Shani, A., andKlug, J.T. 1980a. Photooxidation of (Z,E)-9,11-tetradecadienyl acetate, the main component of the sex pheromone of the female Egyptian cotton leafworm (Spodoptera littoralis).Tetrahedron Lett. 21:1563–1564.
Shani, A., andKlug, J.T. 1980b. Sex pheromone of Egyptian cotton leafworm (Spodoptera littoralis): Its chemical transformations under field conditions.J. Chem. Ecol. 6:875–881.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Ideses, R., Shani, A. & Klug, J.T. Sex pheromone of European grapevine moth (Lobesia botrana) its chemical transformations in sunlight and heat. J Chem Ecol 8, 973–980 (1982). https://doi.org/10.1007/BF00987663
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00987663