Abstract
New sex pheromone component of femaleStegobium paniceum L. was isolated and identified as 2,3-dihydro-2,3,5-trimethyI-6-(1′-methyl-2′-hydroxybutyl)-4H-pyran-4-one, stegobiol, by spectral data and chemical conversion from stegobinone. Relative configuration at C-2, C-3, and C-1′ was determined as 2S,3R,1′S by the conversion from (2S,3R,1′R)-stegobinone. This new sex pheromone elicits the pheromonal response from the species.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Azab, A.K. 1954. Observations on the biological races ofStegobium paniceum L.Bull. Soc. Found ler Entomol 38:59–80.
Hoffmann, R.W., Ladner, W., Steinbach, K., Massa, W., Schmidt, R., andSnatzke, G. 1981. Absolute Konfiguration von Stegobinon.Chem. Ber. 114:2786–2801.
Kodama, H., Mochizuki, K., Kohno, M., Ohnishi, A., andKuwahara, Y. 1987. Inhibition of male response of drugstore beetles to stegobinone by its isomer.J. Chem. Ecol. 13:1859–1869.
Kuwahara, Y., Fukami, H., Ishii, S., Matsumura, F., andBurkholder, W.E. 1975. Studies on the isolation and bioassay of the sex pheromone of the drugstore beetle,Stegobium paniceum (Coleoptera: Anobiidae).J. Chem. Ecol. 1:413–422.
Kuwahara, Y. Fukami, H., Howard, R., Ishii, S., Matsumura, F., andBurkholder, W.E., 1978. Chemical studies on the Anobiidae: Sex pheromone of the drugstore beetle,Stegobium paniceum (L.) (Coleoptera).Tetrahedron 34:1769–1774.
Ono, M., Ohnishi, I., Kuwahara, Y., Chuman, T., andKato, K., 1983. Synthesis of (+)-2,3-cis-stegobinone, (+)-cis-2,3-dihydro-2,3,5-trimethyl-6-(1-methyl-2-oxobutyl)-4H-pyran-4-one, the sex pheromone of drugstore beetle.Agric. Biol. Chem. 47:1933–1934.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kodama, H., Ono, M., Kohno, M. et al. Stegobiol, a new sex pheromone component of drugstore beetle (Stegobium paniceum L.). J Chem Ecol 13, 1871–1879 (1987). https://doi.org/10.1007/BF01013236
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01013236