Journal of Chemical Ecology

, Volume 5, Issue 6, pp 955–966 | Cite as

Isolation, identification, and synthesis of a female sex pheromone of the navel orangeworm,Amyelois transitella (Lepidoptera: Pyralidae)

  • J. A. Coffelt
  • K. W. Vick
  • P. E. Sonnet
  • R. E. Doolittle


A sex pheromone of the navel orangeworm,Amyelois transitella (Walker), was obtained from ether rinses of the sex pheromone gland of calling females. The pheromone was isolated by means of liquid and gas chromatography and was identified as one of four possible geometrical isomers of 11,13-hexadecadienal by means of spectroscopic and microchemical methods. Synthesis and laboratory bioassay of all four isomers revealed that only the (Z,Z) isomer was biologically active. (Z,Z)-11,13-hexadecadienal elicited quantitatively similar activation and attraction responses byA. transitella males as did the natural product.

Key words

Sex pheromone navel orangeworm Amyelois transitella (Z,Z)-11,13-hexadecadienal Pyralidae 


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  1. Beroza, M., andBierl, B.A. 1967. Rapid determination of olefon position in organic compounds of microgram range by ozonolysis and gas chromatography.Anal. Chem. 39:1131–1135.Google Scholar
  2. Butenandt, A., Hecker, E., Hopp, M., andKoch, W. 1962. Sexual attractants of the silk moth. IV. Synthesis of bombykol and thecis-trans isomers of 10,12-hexadecadien-l-ol.Justus Liebig's Ann. Chem. 658:39–64.Google Scholar
  3. Coffelt, J.A., Sower, L.L., andVick, K.W. 1978. Quantitative analysis of identified compounds in pheromone gland rinses ofPlodia interpunctella andEphestia cautella at different times of day.Environ. Entomol. 7:502–505.Google Scholar
  4. Coffelt, J. A., Vick, K. W., Sower, L.L.,andMcClellan, W.T. 1979. Sex pheromone behavior of the navel orangeworm,Amyelois transitella.Environ. Entomol. 8:587–590.Google Scholar
  5. Goto, G., Shima, T., Masuga, H., Masuska, Y., andHiraga, K. 1975. A stereoselective synthesis of (Z, E)-9,11-tetradecadienyl-1-acetate, a major component of the sex pheromone ofSpodoptera litura.Chem. Lett. 1975:103–106.Google Scholar
  6. Hall, D.R.,Beevor, P.S.,Lester, R.,Poppi, R.G., andNesbitt, B.F. 1975. Synthesis of the major sex pheromone of the Egyptian cotton leaf worm,Spodoptera littoralis. Chem. Ind. 1 Mar, pp. 216–217.Google Scholar
  7. Kasang, G., Kaissling, K.E., Vostrowsky, O.,andBestmann, H.J. 1978. Bombykal, a second pheromone component of the silkworm moth,Bombyx mori L.Agnew. Chem. 17:60.Google Scholar
  8. Madsen, H.F., andSanborn, R.R. 1962. Blacklight traps help determine flights of codling moths and other deciduous fruit pests.Calif. Agric. 16:12–13.Google Scholar
  9. Mitchell, E.R. 1975. Disruption of pheromonal communication among coexistent pest insects with multichemical formulations.BioSci. 25(8):493–499.Google Scholar
  10. Proshold, F. 1967. The effects of gamma radiation on the navel orangeworm,Paramyelois transitella (Walker) (Lepidoptera: Phycitidae), and the feasibility of control with irradiated adults. Ph.D. dissertation, University of California, Berkeley. 130 pp.Google Scholar
  11. Rice, R.E. 1976. A comparison of monitoring techniques for the navel orangeworm.J. Econ. Entomol. 69:25–28.Google Scholar
  12. Rice, R.E., Sadler, L.L., Hoffman, M.L., andJones, R.A. 1976. Egg traps for the navel orangeworm,Paramyelois transitella (Walker).Environ. Entomol. 5:697–700.Google Scholar
  13. Roelofs, W., Comeau, A., Hill, A., andMilicevic, G. 1971. Sex attractant of the codling moth: Characterization with electroantennogram technique.Science 174:297–299.Google Scholar
  14. Roelofs, W.,Kochansky, J., andCarde, R. 1974.Trans-7-cis-9-dodecadien-1-yl acetate. U.S. Patent 3,845,108. Oct 29, 1974. 3 pp.Google Scholar
  15. Smith, L.M., Smith, R.G., Loehr, T.M., Daves, G.D., Jr., Daterman, G.E. andWohleb, R.H. 1978. Douglas fir tussock moth pheromone: Identification of a diene analog of the principal attractant and synthesis of stereochemically defined 1,6-, 2,6-, and 3,6-heneicosadien-11-ones.J. Org. Chem. 43:2361–2366.Google Scholar
  16. Sower, L.L., Coffelt, J.A., andVick, K.W. 1973a. Sex pheromone: A simple method of obtaining relatively pure material from females of five species of moths.J. Econ. Entomol. 66:1220–1221.Google Scholar
  17. Sower, L.L., Vick, K.W.,andLong, J.S. 1973b. Isolation and preliminary biological studies on the female-produced sex pheromone ofSitotroga cerealella.Ann. Entomol. Soc. Am. 66:184–187.Google Scholar
  18. Asoka Srinivasan, G.S. 1969. Sex pheromone of the navel orangeworm,Paramyelois transitella (Walker) (Lepidoptera: Phycitidae): Its biological and ecological significance. Ph. D. dissertation, University of California, Berkeley. 119 pp.Google Scholar
  19. Summers, F.M. andPrice, D.W. 1964. Control of navel orangeworm.Calif. Agric. 18:14–15.Google Scholar
  20. Tamaki, Y., Noguchi, H., andYushima, T. 1973. Sex pheromone ofSpodoptera litura (Lepidoptera:Noctuidae) isolation, identification and synthesis.Appl. Entomol. Zool. 8:200–203.Google Scholar
  21. Truscheit, E., andEiter, K. 1962. Synthesis of four isomeric 10,12-hexadecadien-ols.Justus Liebig's Ann. Chem. 658:65–90.Google Scholar

Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • J. A. Coffelt
    • 1
  • K. W. Vick
    • 1
  • P. E. Sonnet
    • 1
  • R. E. Doolittle
    • 1
  1. 1.Insect Attractants, Behavior and Basic Biology Research LaboratoryAgricultural Research, Science and Education Administration, USDAGainesville

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