Journal of Chemical Ecology

, Volume 19, Issue 1, pp 143–157 | Cite as

Electrophysiological and behavioral responses of turnip moth males,Agrotis segetum to fluorinated pheromone analogs

  • Wu Wenqi
  • Marie Bengtsson
  • Bill S. Hansson
  • Tommy Liljefors
  • Christer Löfstedt
  • Glenn D. Prestwich
  • Wei-Chuan Sun
  • Mats Svensson


The electrophysiological and behavioral responses of maleAgrotis segetum to fluorinated analogs of (Z)-5-decenyl acetate (Z5-10∶OAc) were investigated. The single sensillum recordings showed that 4,4-difluoro-(Z)-5-decenyl acetate (4,4-F2), 7,7-difluoro-(Z)-5-decenyl acetate (7,7-F2), 10,10,10-trifluoro-(Z)-5-decenyl acetate (10,10,10-F3) and 7,7,8,8-tetrafluoro-(Z)-5-decenyl acetate (7,7,8,8-F4) were each 100-fold less active than the natural Z5-10 ∶ OAc, whereas the 7,7,8,8,9,9,10,10,10-nonafluoro-(Z)-5-decenyl acetate (F9) analog was essentially inactive. A mixture of Z5-10 ∶ OAc, Z7-12 ∶ OAc, and Z9-14 ∶ OAc on a filter paper dispenser was as attractive as female gland extracts when tested in a flight tunnel. With Z5-10∶OAc omitted, the two-component mixture elicited a significantly lower male response. Four analogs, 7,7-F2, 10,10,10-F3, 7,7,8,8-F4, and F9, were added separately to the two-component mixture to replace Z5-10∶OAc. The responses elicited by the mixtures containing the 7,7-F2, 10,10,10-F3, and 7,7,8,8-F4 analogs did not differ significantly from that of the natural three-component mixture and the two-component mixture, whereas the mixture containing F9 elicited a significantly lower male response, as low as the response to the two-component mixture. In a field test the mixtures containing 10,10,10-F3 and 7,7,8,8-F4 were significantly more active than the two-component mixture, but still less active than the natural three-component mixture. It appears that field tests provided greater discrimination among pheromone analogs in assessing their behavioral activity than the flight-tunnel test did. Structure-activity analyses demonstrate the importance of the lipophilic interaction between the terminal alkyl chain and the receptor site for the activity of the stimulus. The lipophobicity of the fluorinated analogs impedes a productive receptor interaction.

Key Words

Agrotis segetum Lepidoptera Noctuidae (Z)-5-decenyl acetate fluorinated analogs behavioral activity electrophysiological activity flight tunnel single sensillum recording field test lipophobicity lipid solubility structure-activity analysis pheromone 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Anderbrant, O., Löfqvist, J., Jönsson, J., andMarling, E. 1989. Effects of pheromone trap type, position and colour on the catch of the pine sawflyNeodiprion sertifer (Geoff.) (Hym., Diprionidae).J. Appl. Entomol. 107:365–369.Google Scholar
  2. Arn, H., Esbjerg, P., Bues, R., TÒth, M., Szöcs, G., Guerin, P., andRauscher, S. 1983. Field attraction ofAgrotis segetum males in four European countries to mixtures containing three homologous acetates.J. Chem. Ecol. 9:267–276.Google Scholar
  3. Baker, T.C., andRoelofs, W.L. 1981. Initiation and termination of oriental fruit moth male response to pheromone concentrations in the field.Environ. Entomol. 10:211–218.Google Scholar
  4. Baker, T.C., Hansson, B.S., Löfstedt, C., andLöfqvist, J. 1988. Adaptation of antennal neurons in moths is associated with cessation of pheromone-mediated upwind flight.Proc. Natl. Acad. Sci. U.S.A. 85:9826–9830.PubMedGoogle Scholar
  5. Bengtsson, M. 1988. Structure-activity relationships for analogues of (Z)-5-decenyl acetate, a sex pheromone component of the turnip moth,Agrotis segetum. Synthesis and conformational analysis. PhD thesis. University of Lund, Sweden.Google Scholar
  6. Bengtsson, M., Liljefors, T., andHansson, B.S. 1987. Dienic analogues of (Z)-5-decenyl acetates, a pheromone component of the turnip moth,Agrotis segetum: Synthesis, conformational analysis and structure-activity relationships.Bioorg. Chem. 15:409–422.Google Scholar
  7. Bengtsson, M., Rauscher, S., Arn, H., Sun, W.-C., andPrestwich, G.D. 1990a. Fluorinesubstituted pheromone components affect the behaviour of the grape berry moth.Experientia 46:1211–1213.Google Scholar
  8. Bengtsson, M., Liljefors, T., Hansson, B.S., Löfstedt, C., andCopaja, S.V. 1990b. Structure-activity relationships for chain-shortened analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum.J. Chem. Ecol. 16:667–684.Google Scholar
  9. Briggs, G.G., Cayley, G.R., Griffiths, D.C., Macaulay, E.D., Pickett, J.A., Pile, M.M., Wadhams, L.J., andWoodcock, C.K. 1986. Some fluorine containing pheromone analogues.Pestic. Sci. 17:441–448.Google Scholar
  10. Burkert, U., andAllinger, N.L. 1982. Molecular Mechanics. American Chemical Society, Washington, D.C.The MM2(91) program is available from the Quantum Chemistry Program Exchange, University of Indiana, Bloomington, Indiana 47405, and from Molecular Design Ltd., 2132 Farallon Drive, San Leandro, California 94577. A Macintosh version is available from InStar Software AB, IDEON Research Park, S-223 70 Lund, Sweden.Google Scholar
  11. Camps, F., Coll, J., Guerrero, A., andRiba, M. 1984. Fluorinated analogs of insect sex pheromones.Experientia 40:933–934.Google Scholar
  12. Dickens, J.C., Prestwich, G.D., andSun, W.-C. 1991a. Behavioral and neurosensory responses of the boll weevil,Anthonomus grandis Boh. (Coleoptera: Curculionidae), to fluorinated analogs of aldehyde components of its pheromone.J. Chem. Ecol. 17:1007–1020.Google Scholar
  13. Dickens, J.C., Prestwich, G.D., Sun, W.-C., andMori, K. 1991b. Receptor site analysis using neurosensory responses of the boll weevil to analogs of the cyclohexylidene ethanol of its aggregation pheromone.Chem. Senses 16:239–250.Google Scholar
  14. Dykyj, J., andRepás, M. 1979. The Vapour Pressure of Organic Compounds (in Slovak). Veda, Bratislava.Google Scholar
  15. Hildebrand, J.H., Fisher, B.B., andBenesi, H.A. 1950. Solubility of perfluoro-n-heptane with benzene, carbon tetrachloride, chloroform,n-heptane and 2,2,4-trimethylpentane.J. Am. Chem. Soc. 72:4348–4351.Google Scholar
  16. Hinks, C.F., andByers, J.R. 1976. Biosystematics of the genusEuxoa (Lepidoptera: Noctuidae) V. Rearing procedures and life cycles of 36 species.Can. Entomol. 108:1345–1357.Google Scholar
  17. Jönsson, S. 1991. Studies on the complementarity between a moth sex pheromone component and its receptor. Synthesis and structure-activity relationships. PhD thesis. University of Lund, Sweden.Google Scholar
  18. Jönsson, S., Liljefors, T., andHansson, B.S. 1991a. Alkyl substitution in terminal chain of (Z)-5-decenyl acetate, a pheromone component of turnip moth,Agrotis segetum. Synthesis, singlesensillum recordings, and structure-activity relationships.J. Chem. Ecol. 17:103–122.Google Scholar
  19. Jönsson, S., Liljefors, T., andHansson, B.S. 1991b. Replacement of the terminal methyl group in a moth sex pheromone component by a halogen atom. Hydrophobicity and size effects on the electrophysiological single-cell activities.J. Chem. Ecol. 17:1381–1397.Google Scholar
  20. Kaissling, K.-E. 1974. Sensory transduction in insect olfactory receptors, pp. 243–273,in L. Jaenicke (ed.). Biochemistry of Sensory Functions. Springer-Verlag, Berlin.Google Scholar
  21. Liljefors, T., Thelin, B., Van Der Pers, J.N.C., andLöfstedt, C. 1985. Chain-elongated analogs of a pheromone component of the turnip moth,Agrotis segetum. A structure-activity study using molecular mechanics.J. Chem. Soc. Perkin. Trans. 2:1957–1962.Google Scholar
  22. Liljefors, T., Bengtsson, M., andHansson, B.S. 1987. Effects of double-bond configuration on interaction between a moth sex pheromone component and its receptor. A receptor-interaction model based on molecular mechanics.J. Chem. Ecol. 13:2023–2040.Google Scholar
  23. Linn, C., Roelofs, W.L., Sun, W.-C., andPrestwich, G.D. 1992. Activity of perfluorobutylcontaining pheromone components in pheromone blend of cabbage looper moth,Trichoplusia ni.J. Chem. Ecol. 18:737–748.Google Scholar
  24. Löfstedt, C., andHerrebout, W.M. 1988. Sex pheromones of ermine moths on European spindle tree.Entomol. Exp. Appl. 46:29–38.Google Scholar
  25. Löfstedt, C., Van Der Pers, J.N.C, Löfqvist, J., Lanne, B.S., Appelgren, M., Bergström, G., andThelin, B. 1982. Sex pheromone components of the turnip mothAgrotis segetum: Chemical identification, electrophysiological evaluation and behavioural activity.J. Chem. Ecol. 8:1305–1321.Google Scholar
  26. Masnyk, M., Fried, J., andRoelofs, W.L. 1989. Synthesis and pheromonal properties of (Z)-7,7-difluoro-8-dodecenyl acetate, a difluoro derivative of the sex pheromone of the oriental fruit moth.Tetrahedron Lett. 25:3243–3245.Google Scholar
  27. McDonough, L.M. 1991. Controlled release of insect sex pheromones from a natural rubber substrate, pp. 106–124,in P.A. Hedin (ed.). Naturally Occurring Pest Bioregulators. ACS symposium series 449, ACS, Washington, D.C.Google Scholar
  28. McLean, J.A., Morgan, B., Sweeney, J.D., andWeiler, L. 1989. Behavior and survival of western spruce budworm,Choristoneura occidentalis Freeman, exposed to anΩ-fluorinated pheromone analogue.J. Chem. Ecol. 15:91–103.Google Scholar
  29. Olsson, A.-M., Jönsson, J.-å., Thelin, B., andLiljefors, T. 1983. Determination of the vapor pressures of moth sex pheromone components by a gas chromatographic method.J. Chem. Ecol. 9:375–385.Google Scholar
  30. Prestwich, G.D. 1987a. Chemistry of pheromone and hormone metabolism in insects.Science 237:999–1006.PubMedGoogle Scholar
  31. Prestwich, G.D. 1987b. Chemical studies of pheromone reception and catabolism, pp. 473–527,in G.D. Prestwich, and G.J. Blomquist (eds.). Pheromone Biochemistry. Academic Press, New York.Google Scholar
  32. Prestwich, G.D. 1992. Chemical studies of pheromone and hormone receptors in insects.Arch. Insect Biochem. Physiol. In press.Google Scholar
  33. Prestwich, G.D., Carvalho, J.F., Ding, Y.-S., andHendricks, D.E. 1986. Acyl fluorides as reactive mimics of aldehyde pheromones: Hyperactivation and aphrodisia inHeliothis virescens.Experientia 42:964–966.Google Scholar
  34. Prestwich, G.D., Sun, W.-C., andDickens, J.C. 1988. Fluorinated analogs of the aldehyde components of the boll weevil pheromone: Synthesis and biological activity.J. Chem. Ecol. 14:1427–1439.Google Scholar
  35. Prestwich, G.D., Sun, W.-C., Mayer, M.S., andDickens, J.C. 1990. Perfiuorinated moth pheromones, synthesis, and electrophysiological activity.J. Chem. Ecol. 6:1761–1778.Google Scholar
  36. Ryan, J.A. 1960. Significance tests for multiple comparison of proportions, variances and other statistics.Psychol. Bull. 57:318–328.PubMedGoogle Scholar
  37. Sun, W.-C., Ng, C.-S., andPrestwich, G.D. 1992. Synthesis of partially fluorinated analogues of (Z)-5-decenyl acetate: Probes for hydrophobic interaction in pheromone reception.J. Org. Chem. 57:132–137.Google Scholar
  38. Turberg, M.P., andBrady, J.E. 1988. Semifluorinated hydrocarbons: Primitive surfactant molecules.J. Am. Chem. Soc. 110:7797–7801.Google Scholar
  39. Van Der Pers, J.N.C., andDen Otter, C.J. 1978. Single cell responses from olfactory receptors of small ermine moths to sex attractants.J. Insect Physiol. 24:337–343.Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • Wu Wenqi
    • 1
  • Marie Bengtsson
    • 2
  • Bill S. Hansson
    • 1
  • Tommy Liljefors
    • 3
  • Christer Löfstedt
    • 1
  • Glenn D. Prestwich
    • 4
  • Wei-Chuan Sun
    • 4
  • Mats Svensson
    • 1
  1. 1.Department of EcologyLund UniversityLundSweden
  2. 2.Department of Plant and Forest ProtectionSwedish University of Agricultural SciencesLundSweden
  3. 3.Department of Organic Chemistry 3Lund UniversityLundSweden
  4. 4.Department of ChemistryState University of New YorkStony Brook

Personalised recommendations