Journal of Chemical Ecology

, Volume 17, Issue 12, pp 2437–2447 | Cite as

Synthesis of the stereoisomers of the female sex pheromone of the Hessian fly,Mayetiola destructor

  • Jocelyn G. Millar
  • Stephen P. Foster
  • Marion O. Harris


The female-produced sex pheromone of the Hessian fly,Mayetiola destructor (Say) (Diptera: Cecidomyiidae), has been identified as (10E)-tridecen-2-yl acetate. A flexible synthetic route was developed which allowed access to the chiral and racemic forms of the pheromone, and to the 10Z stereoisomer of the pheromone. The natural compound was determined to have the 2S configuration by hydrolysis of the acetate function, derivatization of the resulting alcohol with (2S)-2-acetoxypropionyl chloride, and capillary gas Chromatographic comparison of the derivative with the corresponding derivatives prepared from the synthetic enantiomers. Trace amounts of the 10Z isomer of the pheromone have also been detected in extracts of female Hessian fly ovipositors, along with (10E)-tridecen-2-ol and 2-tridecanyl acetate. Due to the small quantities of these compounds available from ovipositor extracts, the chirality of the trace components has not yet been determined.

Key words

(10E)-tridecen-2-yl acetate (10Z)-tridecen-2-yl acetate sex pheromone Diptera Cecodomyiidae Hessian fly Mayetiola destructor 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Abrams, S.R., andShaw, A.C. 1988. Triple bond isomerizations: 2- to 9-decyn-1-ol.Org. Syn. 66:127–131.Google Scholar
  2. Brandsma, L. 1971. Preparative Acetylenic Chemistry. Elsevier Publishing Co., New York.Google Scholar
  3. Brown, C.A., andAhuja, V.K. 1973. “P-2 nickel” catalyst with ethylenediamine, a novel system for highly stereospecific reduction of alkynes tocis olefins.J. C.S. Chem. Commun. 553–554.Google Scholar
  4. Cartwright, W.B. 1922. Sexual attraction of the female Hessian fly.Can. Entomol. 54:154.Google Scholar
  5. Chaudhury, M.F.B., Ball, H.J., andJones, C.M. 1972. A sex pheromone of the female face fly,Musca autumnalis (Diptera: Muscidae) and its role in sexual behavior.Ann. Entomol. Soc. Am. 65:607–612.Google Scholar
  6. Feldman, M. N.W. Simmons (ed.). Evolution of Crop Plants. Longman, London.Google Scholar
  7. Foster, J.E.,Taylor, P.L., andAraya, J.E. 1986. The Hessian fly.Purdue Univ. Ag. Exp. Stn. Bull. No. 502, West Lafayette, Indiana, 21 pp.Google Scholar
  8. Foster, S.P., Harris, M.O., andMillar, J.G. 1991. Identification of the sex pheromone of the Hessian fly,Mayetiola destructor (Say).Naturwissenschaften 78:130–131.Google Scholar
  9. Gallun, R.L.,Deay, H.O., andCartwright, W.B. 1961. Four races of Hessian fly selected and developed from an Indiana population.Purdue Univ. Agric. Expt. Stn. Res. Bull. 732, Lafayette, Indiana.Google Scholar
  10. Harris, M.O., andFoster, S.P. 1991. Wind tunnel studies of sex pheromone-mediated behavior of the Hessian fly (Diptera: Cecodomyiidae).J. Chem. Ecol. Submitted.Google Scholar
  11. Henrick, C.A., Carney, R.L., andAnderson, R.J. 1982. Some Aspects of the Synthesis of Insect Sex B.A. Leonhardt and M. Beroza (eds.). Insect Pheromone Technology: Chemistry and Applications. American Chemical Society, Washington D.C. pp. 27–60.Google Scholar
  12. Johnston, B.D., andOehlschlager, A.C. 1984. Synthesis of the aggregation pheromone of the square-necked grain beetleCathartus quadricollis.J. Org. Chem. 51:760–763.Google Scholar
  13. Kruizinga, W.H., Strijtveen, B., andKellogg, R.M. 1981. Cesium carboxylates in dimethyl-formamide. Reagents for introduction of hydroxyl groups by nucleophilic substitution and for inversion of configuration of secondary alcohols.J. Org. Chem. 46:4321–4323.Google Scholar
  14. Mackay, P.A., andHatchett, J.H. 1984. Mating behavior and evidence of a female sex pheromone in the Hessian fly,Mayetiola destructor (Say) (Diptera: Cecidomyiidae).Ann. Entomol. Soc. Am. 77:616–620.Google Scholar
  15. Oehlschlager, A.C., Czyzewska, E., Aksela, A., andPierce, H.D., Jr. 1985. Improved syntheses of hydroxy acid precursors of macrolide pheromones of cucujid grain beetles.Can. J. Chem. 64:1407–1413.Google Scholar
  16. Slessor, K.N., King, G.G.S., Miller, D.R., Winston, M.L., andCutforth, T.L. 1985. Determination of chirality of alcohol or latent alcohol semiochemicals in individual insects.J. Chem. Ecol. 11:1659–1667.Google Scholar
  17. Utimoto, K., Lambert, C., Fukuda, Y., Shiragami, H., andNozaki, H. 1984. The catalytic action of trimethylgallium on the reaction of aikynyllithium with epoxides.Tetrahedron Lett. 25:5423–5426.Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • Jocelyn G. Millar
    • 1
  • Stephen P. Foster
    • 2
  • Marion O. Harris
    • 3
  1. 1.Department of EntomologyUniversity of CaliforniaRiverside
  2. 2.D.S.I.R. Plant ProtectionPalmerston NorthNew Zealand
  3. 3.Department of EntomologyKansas State UniversityManhattan

Personalised recommendations