Abstract
The sex pheromone of the Comstock mealybug,Pseudococcus comstocki (Kuwana) was isolated from volatiles trapped from air passing over virgin female insects. Combined gas chromatography, mass and infrared spectroscopy, and microreactions indicated that the structure was 2,6-dimethyl-1,5-heptadien-3-ol acetate. This was confirmed by synthesis; several analogs were also prepared. The natural and synthetic pheromone caused similar trap capture of male insects. Synthetic analogs were significantly less attractive in field tests and the addition of minor amounts of the corresponding alcohol to the pheromone appeared to enhance trap capture, but the results were not statistically conclusive.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Anonymous. 1974. Pheromone traps Comstock mealybug.Agric Res 23(3):16.
Bartlett, B.R., andClancy, D.W. 1972. The Comstock mealybug in California and observations on some of its natural enemies.J. Econ. Entomol. 65:1329–1332.
Beroza, M., andBierl, B.A. 1969. Ozone generator for micro-analysis.Mikrochim. Acta 3:720–723.
Bieri, B.A., Beroza, M., andAshton, W.T. 1969. Reaction loops for reaction gas chromatography. Subtraction of alcohols, aldehydes, ketones, epoxides, and acids and carbon-skeleton chromatography of polar compounds.Mikrochim. Acta 3:637–653.
Bierl-Leonhardt, B.A., Moreno, D.S., Schwarz, M., Forster, H.S., Plimmer, J.R., andDeVilbiss, E.D. 1980. Identification of the pheromone of the Comstock mealybug.Life Sci. 27:399–402.
Bierl-Leonhardt, B.A., andDevilbiss, E.D. 1981. Structure identification of terpene-type alcohols at microgram levels.Anal. Chem. 53:936–938.
Cox, J.A. 1940. Comstock's mealybug on apple and catalpa.J. Econ. Entomol. 33:445–447.
Cutright, C.R. 1951. Comstock mealybug in Ohio.J. Econ. Entomol. 44:123–125.
Dale, J.A., Dull, D.L., andMosher, H.S. 1969. α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines.J. Org. Chem. 34:2543–2549.
Hough, W.S. 1925. Biology and control of Comstock's mealybug on the umbrella catalpa.Va. Agric. Exp. Stn. Tech. Bull. 29:17pp.
Kovats, E. 1966. Gas Chromatographic characterization of organic substances in the retention index system, pp. 229–247,in J.C. Giddingsand R.A. Keller (eds.). Advances in Chromatography, Vol. 1. Marcel Dekker, New York.
Meyerdirk, D.E., andNewell, I.M. 1979. Seasonal development and flight activity ofPseudococcus comstocki in California.Ann. Entomol. Soc. Am. 72:492–494.
Moreno, D., unpublished observations.
Negishi, T., Ishiwatari, T., andAsano, S. 1980. Sex pheromone of the Comstock mealybug,Pseudococcus comstocki Kuwana: Bioassay method, male response-habits to the sex pheromone.Appl. Entomol. Zool. 24:1–5.
Negishi, T., Uchida, M., Tamaki, Y., Mori, K., Ishiwatari, T., Asano, S., andNakagawa, K. 1980. Sex pheromone of the Comstock mealybug,Pseudococcus comstocki Kuwana: Isolation and identification.Appl. Entomol. Zool. 15:328.
Nigam, I.D. 1966. Reaction gas chromatography. I. Catalytic aromatization of alicyclic and heterocyclic compounds.J. Chromatogr. 24:188–192.
Phillips, J.H. 1961. An infestation of Comstock mealybug,Pseudococcus comstocki (Kuw.) (Homoptera: Coccoidea) on peach in Ontario.Proc. Entomol. Soc. Ont. 91:268–270.
Pratt, R.M. 1958. Florida guide to citrus insects, diseases and nutritional disorders in color.Agric. Exp. Stn., Gainesville, Florida.
Tashiro, H., Chambers, D.L., Moreno, D.S., andBeavers, J. 1969. Reproduction in the California red scale,Aonidiella aurantii. III. Development of an olfactometer for bioassay of the female sex pheromone.Ann. Entomol. Soc. Am. 62:935–940.
Terao, S., Shiraishi, M., andKato, K. 1979. A facile synthesis of allylic alcohols.Synthesis 1979:467–468.
Uchida, M., Nakagawa, K., Negishi, T., Asano, S., andMori, K. 1981. Synthesis of 2,6-dimethyl-1,5-heptadien-3-ol acetate, the pheromone of the comstock mealybug,Pseudococcus comstocki Kuwana, and its analogs.Agric. Biol. Chem. 45:369–372.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Bierl-Leonhardt, B.A., Moreno, D.S., Schwarz, M. et al. Isolation, identification, synthesis, and bioassay of the pheromone of the comstock mealybug and some analogs. J Chem Ecol 8, 689–699 (1982). https://doi.org/10.1007/BF00988310
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00988310