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Journal of Chemical Ecology

, Volume 19, Issue 9, pp 1917–1928 | Cite as

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

  • Peter Witzgall
  • Marie Bengtsson
  • C. Rikard Unelius
  • Jan Löfqvist
Article

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.

Key Words

Sex pheromone conjugated diene isomerization attraction inhibitor stereospecific synthesis (E,E)-8,10-dodecadien-1-yl acetate Cydia nigricana Tortricidae Lepidoptera 

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References

  1. 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.Google Scholar
  2. 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.Google Scholar
  3. 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.Google Scholar
  4. 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.Google Scholar
  5. 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.Google Scholar
  6. 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.Google Scholar
  7. 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.Google Scholar
  8. 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.Google Scholar
  9. 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.Google Scholar
  10. Bradley, J.D., Tremewan, W.G., andSmith, A. 1973. British tortricoid moths. Cochylidae and Tortricidae: Tortricinae. The Ray Society, London.Google Scholar
  11. Brown, D.F., andMcDonough, L.M. 1986. Insect sex pheromones: Formulations to increase the stability of conjugated dienes.J. Econ. Entomol. 79:922–924.Google Scholar
  12. 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.Google Scholar
  13. 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.Google Scholar
  14. 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.Google Scholar
  15. 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.Google Scholar
  16. Greenway, A.R. 1984. Sex pheromone of the pea moth,Cydia nigricana (F.) (Lepidoptera: Olethreutidae).J. Chem. Ecol. 10:973–982.Google Scholar
  17. 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.Google Scholar
  18. 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.Google Scholar
  19. 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.Google Scholar
  20. 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.Google Scholar
  21. 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.Google Scholar
  22. 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.Google Scholar
  23. 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.Google Scholar
  24. 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.Google Scholar
  25. 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.Google Scholar
  26. Wall, C. 1988. Application of sex attractants for monitoring the pea moth,Cydia nigricana (F.) (Lepidoptera: Tortricidae).J. Chem. Ecol. 14:1857–1866.Google Scholar
  27. 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.Google Scholar
  28. Wall, C., andPerry, J.N. 1987. Range of attraction of moth sex-attractant sources.Entomol. Exp. Appl. 44:5–14.Google Scholar
  29. 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.Google Scholar
  30. 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.Google Scholar
  31. 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.Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • Peter Witzgall
    • 1
  • Marie Bengtsson
    • 2
  • C. Rikard Unelius
    • 3
  • Jan Löfqvist
    • 2
  1. 1.Department of EcologyLund UniversityLundSweden
  2. 2.Department of Plant Protection SciencesSwedish University of Agricultural SciencesLundSweden
  3. 3.Department of Organic ChemistryRoyal Institute of TechnologyStockholmSweden

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