Abstract
Field attraction ofCydia nigricana males to synthetic female sex pheromone (E,E)-8,10-dodecadien-1-yl acetate, formulated on red rubber septa, declined continuously during two weeks. This was due to isomerization of (E,E)-8,10-dodecadien-1-yl acetate: eight days after application of purifiedE,E isomer, the proportion ofE,Z;Z,E; andZ,Z isomers in rubber septa aged in the laboratory was 4%; a 5% addition of any one of these isomers to fresh lures of (E,E)-8,10-dodecadien-1-yl acetate significantly reduced male attraction. Stereospecific syntheses of (E,Z)-, (Z,E)-, and (Z,Z)-8,10-dodecadien-1-yl acetate are described. The pheromone gland ofCydia nigricana contains 0.8 ng/female of (E,E)-8,10-dodecadien-1-yl acetate, accompanied by three monounsaturated acetates, (E)-9-dodecen-1-yl acetate, (Z)-5-tetradecen-1-yl acetate, and (Z)-7-tetradecen-1-yl acetate (0.1 ng/female each). These compounds did not augment male trap catch when added to (E,E)-8,10-dodecadien-1-yl acetate.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Ando, T., Kusa, K., Uchiyama, M., Yoshida, S., andTakahashi, N. 1983.13C NMR analyses on conjugated dienic pheromones of Lepidoptere.Agric. Biol. Chem. 47:2849–2853.
Ando, T., Katagiri, Y., andUchiyama, M. 1985. Mass spectra of dodecadienic compounds with a conjugated double-bond, lepidopterous sex pheromones.Agric. Biol. Chem. 49:413–421.
Arn, H., Rauscher, S., andSchmid, A. 1979. Sex attractant formulations and traps for the grape mothEupoecilia ambiguella Hb.Mitt. Schweiz. Entomol. Ges. 52:49–55.
Arn, H., Guerin, P.M., Buser, H.-R., Rauscher, S., andMani, E. 1985. Sex pheromone blend of the codling moth,Cydia pomonella: Evidence for a behavioural role of dodecan-1-ol.Experientia 41:1482–1483.
Arn, H., Tóth, M., andPriesner, E. 1992. List of Sex Pheromones of Lepidoptera and Related Attractants, 2nd ed. OILB, Swiss Federal Research Station, Wädenswil, Switzerland.
Babler, J.H., andInvergo, B.J. 1979. A convenient stereoselective route to the sex pheromone of the red bollworm moth via an allylic sulfenate to sulfoxide rearrangement.J. Org. Chem. 44:3723–3725.
Baeckström, P., Stridh, K., Li, L., andNorin, T. 1987. Claisen rearrangements with mesityl oxide dimethyl ketal. Synthesis of ipsdienone,E- and Z-ocimenone, 2,6-dimethyl-2,7-octadien-4-one and 2,6-dimethyl-2,7-octadien-4-ol.Acta Chem. Scand. B. 41:442–447.
Bestmann, H.J., Süss, J., andVostrowsky, O. 1978. Pheromone XX. Synthese von (E)-8,(E)-10-Dodecadien-1-ol (Codlemone), dem Sexuallockstoff des Apfelwicklers, seiner Isomeren, Homologen und Derivate.Tetrahedron Lett. 36:3329–3332.
Björkling, F., Norin, T., andUnelius, R. 1985. Synthesis of (8Z, 10Z)-dodecadienyl acetate using a general method applicable to (Z,Z)-1,3-dienes.Synth. Commun. 15:463–472.
Bradley, J.D., Tremewan, W.G., andSmith, A. 1973. British tortricoid moths. Cochylidae and Tortricidae: Tortricinae. The Ray Society, London.
Brown, D.F., andMcDonough, L.M. 1986. Insect sex pheromones: Formulations to increase the stability of conjugated dienes.J. Econ. Entomol. 79:922–924.
Chapman, O.L., Mattes, K.C., Sheridan, R.S., andKlun, J.A. 1978. Stereochemical evidence of dual chemoreceptors for an achiral sex pheromone in Lepidoptera.J. Am. Chem. Soc. 100:4878–4884.
Chisholm, M.D., Reed, D.W., Underhill, E.W., Palaniswamy, P., andWong, J.W. 1985. Attraction of tortricid moths of subfamily Olethreuthinae to field traps baited with dodecadienes.J. Chem. Ecol. 11:217–229.
Davis, H.G., McDonough, L.M., Burditt, A.K., Jr., andBierl-Leonhardt, B.A. 1984. Filbertworm sex pheromone. Identification and field tests of (E,E)-and (E,Z)-8,10-dodecadien-1-ol acetates.J. Chem. Ecol. 10:53–61.
Einhorn, J., Beauvais, F., Gallois, M., Descoins, C., andCausse, R. 1984. Constituants secondaires de la phéromone sexuelle du carpocapse des pommes,Cydia pomonella L. (Lepidoptera, Tortricidae).C.R. Acad. Sci. Paris 299(III):773–778.
Greenway, A.R. 1984. Sex pheromone of the pea moth,Cydia nigricana (F.) (Lepidoptera: Olethreutidae).J. Chem. Ecol. 10:973–982.
Greenway, A.R., andWall, C. 1981. Attractant lures for males of the pea moth,Cydia nigricana (F.) containing (E)-10-dodecen-1-yl acetate and (E,E)-8,10-dodecadien-1-yl acetate.J. Chem. Ecol. 7:563–574.
Greenway, A.R., Wall, C., andPerry, J.N. 1982. Compounds modifying the activity of two sex attractants for males of the pea moth,Cydia nigricana (F.).J. Chem. Ecol. 8:397–408.
Horák, A., Hrdy, I., Konecny, K., andVrkoc, J. 1989. Effect of substrate formulation on the efficacy of the pea moth,Cydia nigricana, sex pheromone lures.Entomol. Exp. Appl. 53:125–132.
Katovich, S.A., Swedenborg, P.D., Giblin, M., andUnderhill, E.W. 1989. Evidence for (E,Z)-8,10-dodecadienyl acetate as the major component of the sex pheromone of the eastern pine seedworm,Cydia toreuta (Lepidoptera: Tortricidae).J. Chem. Ecol. 15:581–590.
Lanne, B.S., Appelgren, M., Bergström, G., andLöfstedt, C. 1985. Determination of the double bond position in monounsatured acetates from their mass spectra.Anal. Chem. 57:1621–1625.
Löfstedt, C., andBengtsson, M. 1988. Sex pheromone biosynthesis of (E,E)-8,10-dodecadienol in codling mothCydia pomonella involvesE9 desaturation.J. Chem. Ecol. 14:903–915.
Macaulay, E.D.M., Etheridge, P., Garthwaite, D.G., Greenway, A.R., Wall, C., andGoodchild, R.E. 1985. Prediction of optimum spraying dates against pea moth,Cydia nigricana (F.), using pheromone traps and temperature measurements.Crop Prot. 4:85–98.
McDonough, L.M., Eikenbary, R.D., Smith, M.T., Davis, H.G., Smithhisler, C.L., Hedger, G.A., Campbell, R.K., Payne, J.A., Reid, W., andMcVay, J.R. 1990. Sex pheromone of hickory shuckwormCydia caryana. Development of an effective field lure.J. Chem. Ecol. 16:317–324.
Rossi, R. 1981. Highly stereoselective synthesis of (Z)-9,11-dodecadien-1-yl acetate; a sex pheromone component ofDiparopsis castanea Hmps.Synthesis 5:359–361.
Wall, C. 1988. Application of sex attractants for monitoring the pea moth,Cydia nigricana (F.) (Lepidoptera: Tortricidae).J. Chem. Ecol. 14:1857–1866.
Wall, C., andPerry, J.N. 1980. Effects of spacing and trap number on interactions between pea mothCydia nigricana pheromone traps.Entomol. Exp. Appl. 28:313–321.
Wall, C., andPerry, J.N. 1987. Range of attraction of moth sex-attractant sources.Entomol. Exp. Appl. 44:5–14.
Wall, C., Bournoville, R., Greenway, A.R., andEinhorn, J. 1987a. Efficacy and stability of sex-attractant lures forCydia nigricana (F.) andCydia medicaginis (Kuzn.).Crop Prot. 6: 7–12.
Wall, C., Garthwaite, D.G., Blood Smyth, J.A., andSherwood, A. 1987b. The efficacy of sex-attractant monitoring for the pea moth,Cydia nigricana, in England, 1980-1985.Ann. Appl. Biol. 110:223–229.
Witzgall, P., andArn, H. 1990. Direct measurement of the flight behavior of male moths to calling females and synthetic sex pheromones.Z. Naturforsch. 45c: 1067–1069.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Witzgall, P., Bengtsson, M., Unelius, C.R. et al. Attraction of pea mothCydia nigricana F. (Lepidoptera: Tortricidae) to female sex pheromone (E,E)-8,10-dodecadien-1-YL acetate, is inhibited by geometric isomersE,Z, Z,E, andZ,Z . J Chem Ecol 19, 1917–1928 (1993). https://doi.org/10.1007/BF00983796
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00983796