Abstract
The male sexual behavior-stimulating and inhibiting properties of a series of analogs of the European corn borer sex pheromone were determined in a flight tunnel. The structural requirements for inhibition of pheromonal response were far less restrictive than those for elicitation of that response. Analogs that by themselves elicited upwind flight response from males at a low dose were generally less inhibitory to male response than many of the analogs that had no pheromonal activity. These findings suggest that many pheromone analogs bind to pheromone receptors without provoking behavioral response and possibly undergo slower degradation on the antenna than pheromonally active compounds. The disparity of response to analogs by two pheromonal types of the European corn borer indicates that the pheromone receptor and pheromone catabolic systems are biochemically very different in the two types.
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References
Allinger, N.L. 1976. Calculation of molecular structure and energy by field-force methods.Adv. Phys. Org. Chem. 13:1–82.
Brückner, C., Buschmann, E., Becker, R., Seufert, W., De Kramer, J.J., andKrieg, W. 1988. A new highly effective synthetic pheromone mimic forLobesia botrana.Z. Naturforsch. 43c:315–318.
Camps, F., Fabrias, G., Gasol, V., Guerrere, A., Hernandez, R., andMontoya, R. 1988. Analogs of the sex pheromone of processionary moth,Thaumetopoea pityocampa: Synthesis and biological activity.J. Chem. Ecol. 14:1331–1346.
Chiang, H.C., Klun, J.A., andSchwarz, M. 1982. The whole China corn borer research group. PRC-US cooperative study on male response to synthetic pheromone in China. International working group onOstrinia nubilalis.Newsletter International Organization for Biological Control of Noxious Animals and Plants (IOBC) 3:4–9.
Eidmann, H.H., Weslien, J., Harding, S., Baeckstroem, P., Norin, T., andVrkoc, J. 1986. A compound replacing a natural pheromone component of the spruce bark beetle.Naturwissenschaften 73:629–630.
Glover, T.J., Perez, N., andRoelofs, W.L. 1989. Comparative analysis of sex-pheromone-response antagonists in three races of European corn borer.J. Chem. Ecol. 15:863–873.
Klun, J.A., andHuettel, M.D. 1988. Genetic regulation of sex pheromone production and response: Interaction of sympatric pheromonal types of European corn borer,Ostrinia nubilalis.J. Chem. Ecol. 14:2047–2061.
Klun, J.A., andMaini, S. 1979. Genetic basis of an insect chemical communication system: The European corn borer,Ostrinia nubilalis.Environ. Entomol. 8:423–426.
Klun, J.A., Maini, S., Chapman, O.L., Lepone, G., andLee, G.-H. 1979. Suppression of male European corn borer sex attraction and precopulatory reactions with (E)-9-tetradecenyl acetate.J. Chem. Ecol. 5:345–352.
Klun, J.A., Bierl-Leonhardt, B.A., Schwarz, M., Litsinger, J.A., Barrion, A.T., Chiang, H.C., andJiang, Z. 1980. Sex pheromone of the Asian corn borer moth.Life Sci. 27:1603–1606.
Liljefors, T.,Thelin, B.,Van Der Pers, J.N.C., andLöfstedt, C. 1985. Chain elongated analogues of a pheromone component of the turnip moth,Agrotis segetum. A structure activity study using molecular mechanics.J. Chem. Soc. Perkin Trans. II 1957–1962.
Macaulay, S.R. 1980. Isomerization of internal triple bonds of alkynols with sodium hydride in 1,3-diaminopropane.J. Org. Chem. 45:734–735.
Mason, J.R., andMorton, T.H. 1984. Fast and loose covalent binding of ketones as a molecular mechanism in vertebrate olfactory receptors: Chemical production of selective anosmia.Tetrahedron 40:483–492.
Minks, A.K., andCardé, R.T. 1988. Disruption of pheromone communication in moths: Is the natural blend really most efficacious?Entomol. Exp. Appl. 49:25–36.
Preiss, R., andPriesner, E. 1988. Responses of male codling moths to codlemone and other alcohols in a wind tunnel.J. Chem. Ecol. 14:797–813.
Prestwich, G.D., Vogt, R.G., andRiddiford, L.M. 1986. Binding and hydrolysis of radiolabeled pheromone and several analogs by male-specific antennal proteins of the mothAntheraea polyphemus.J. Chem. Ecol. 12:323–333.
Prestwich, G.D., Graham, S.McG., Kuo, J.W., andVogt, R.G., 1989. Tritium-labeled enantiomers of disparlure. Synthesis and in vitro metabolism.J. Am. Chem. Soc. 111:636–642.
Raina, A.K., Klun, J.A., Schwarz, M., Day, A., Leonhardt, B.A., andDouglass, L.W. 1986. Female sex pheromone of the melonworm,Dyaphania hyalinata, and analysis of male responses to pheromone in a flight tunnel.J. Chem. Ecol. 12:229–237.
SAS Institute, 1988. SAS Users Guide: Release 6.03. SAS Institute Inc., Cary, North Carolina.
Schwarz, M., Klun, J.A., Hart, E.R., Leonhardt, B.A., andWeatherby, J.C. 1983. Female sex pheromone of the yellowheaded fireworm,Acleris minuta.Environ Entomol. 12:1253–1256.
Schwarz, M., Graminski, G.F., andWaters, R.M. 1986. Insect sex pheromones: Stereospecific synthesis of (E)-13,13-dimethyl-11-tetradecen-1-ol acetate via a thiophenol-mediated olefin inversion.J. Org. Chem. 51:260–263.
Schwarz, M., Klun, J.A., Fritz, G.L., Uebel, E.C., andRaina, A.K. 1989. European corn borer sex pheromone: Structure-activity relationships,J. Chem. Ecol. 15:601–617.
Struble, D.L., Byers, J.R., Mcleod, D.G.R., andAyre, G.L. 1987. Sex pheromone components of an Alberta population of European corn borer,Ostrinia nubilalis, Can. Entomol. 119:291–299.
Vogt, R.G. 1987. The molecular basis of pheromone reception: Its influence on behavior, pp. 385–431,in G.D. Prestwich and G.J. Blomquist (eds.). Pheromone Biochemistry, Academic Press, New York.
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Schwarz, M., Klun, J.A. & Uebel, E.C. European corn borer sex pheromone. J Chem Ecol 16, 1591–1604 (1990). https://doi.org/10.1007/BF01014092
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DOI: https://doi.org/10.1007/BF01014092