Abstract
Reinvestigation of the pheromonal activity of anhydroserricornin, (2S,3S)-2,6-diethyl-3,5-dimethyl-3,4-dihydro-2H-pyran, showed that the magnitude of its activity was less than 1/103 of that of serricornin, 7-hydroxy-4,6-dimethyl-3-nonanone, the sex pheromone of the cigarette beetleLasioderma serricorne (F.). Neither a synergistic nor an inhibitory effect of anhydroserricornin addition on the action of serricornin was observed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Chuman, T., Kohno, M., Kato, K., andNoguchi, M. 1979a. 4,6-Dimethyl-7-hydroxy-nonan-3-one, a sex pheromone of the cigarette beetle (Lasioderma serricorne F.).Tetrahedron Lett. 1979:2361–2364.
Chuman, T., Kato, K., andNoguchi, M. 1979b. Synthesis of (±)-serricornin, 4,6-dimethyl-7-hydroxy-nonan-3-one, a sex pheromone of cigarette beetle (Lasioderma serricorne F.).Agric. Biol. Chem. 43:2005.
Chuman, T., Mochizuki, K., Mori, M., Kohno, M., Ono, M., Onishi, I., andKato, K. 1982a. The pheromone activity of (±)-serricornins for male cigarette beetle (Lasioderma serricorne F.).Agric. Biol. Chem. 46:593–595.
Chuman, T., Mochizuki, K., Mori, M., Kohno, M., Kato, K., Nomi, H., andMori, K. 1982b. Behavioral and electroantennogram responses of male cigarette beetle (Lasioderma serricorne F.) to optically active serricornins.Agric Biol. Chem. 46:3109–3112.
Fletcher, L.W., Garrett, L.C., andWakabayashi, N. 1984. Evaluation of serricornin as a sex attractant for cigarette beetles.Tobacco Sci. 28:93–98.
Hoffmann, R.W., Helbig, W., andLadner, W. 1982. Synthesis of 6S,7S-anhydroserricornin.Tetrahedron Lett. 23:3479–3482.
Hoffmann, R.W., Ladner, W., andHelbig, W. 1984. Stereoselective synthesis of alcohols, XVIII. Synthesis of (3S,4S)-4-methyl-3-heptanol and of (5S,6S)-anhydroserricornin.Liebigs Ann. Chem. 1984:1170–1179.
Levinson, H.Z., Levinson, A.R., Francke, W., Mackenroth.,W., andHeemann, V. 1981. The pheromone activity of anhydroserricornin and serricornin for male cigarette beetles (Lasioderma serricorne F.).Naturwissenschaften 68:148–149.
Levinson, H.Z., Levinson, A.R., Francke, W., Mackenroth.,W., andHeemann, V. 1982. Supressed pheromone responses of male tobacco beetles to anhydroserricornin in presence of serricornin.Naturwissenschaften 69:454–455.
Mori, K., andWatanabe, H. 1985. A new synthesis of serricornin [(4S,6S,7S)-7-hydroxy-3,4-dimethyl-3-nonanone], the sex pheromone of the cigarette beetles.Tetrahedron 41:3423–3428.
Mori, M., Chuman, T., Kohno, M., Kato, K., Noguchi, M., Nomi, H., andMori, K. 1982a. Absolute stereochemistry of serricornin, the sex pheromone of the cigarette beetle, as determined by the synthesis of its (4S,6S,7R)-isomer.Tetrahedron Lett. 23:667–670.
Mori, M., Chuman, T., Kato, K., andMori, K. 1982b. A Stereoselective synthesis of “natural” (4S,6S,7S)-serricornin, the sex pheromone of cigarette beetle, from levoglucosenone.Tetrahedron Lett. 23:4593–4596.
Mori, M., Chuman, T., Kato, K., andMori, K. 1984. Studies on the synthesis of serricornin. Abstract of papers, 45th Symposium on Synthetic Organic Chemistry, the Society of Synthetic Organic Chemistry of Japan, Tokyo 1984, p. 101.
Mori, M., Mochizuki, K., Kohno, M., Chuman, T., Ohnishi, A., Watanabe, H., andMori, K. 1985. Inhibitory action of (4S,6S,7R)-isomer to the pheromonal activity of serricornin, (4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone.J. Chem. Ecol. 12:83–89.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Mochizuki, K., Mori, M., Chuman, T. et al. Reinvestigation of anhydroserricornin, (2S,3S)-2,6-diethyl-3,5-dimethyl-3,4-dihydro-2H-pyran, as a sex pheromone component for male cigarette beetle. J Chem Ecol 12, 179–186 (1986). https://doi.org/10.1007/BF01045601
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01045601