Journal of Chemical Ecology

, Volume 16, Issue 12, pp 3493–3510 | Cite as

Trail pheromone of the antTetramorium impurum and model compounds: Structure-activity comparisons

  • E. David Morgan
  • Brian D. Jackson
  • David G. Ollett
  • Geoffrey W. Sales


The major component of the trail pheromone ofT. impurum is methyl 2-hydroxy-6-methylbenzoate (methyl 6-methyl salicylate). The poison reservoir of each worker contains about 1.0 ng of this substance in the venom. To ascertain the degree of specificity of the substance as pheromone and to determine any correlation between structure and biological activity, 38 synthetic analogs were tested in a bioassay. Sixteen compounds showed activity at 100 ng per artificial trail. The importance of the methyl group and methyl ester were demonstrated, while the hydroxyl group has a relatively small effect.

Key Words

Tetramorium impurum Hymenoptera Formicidae trail pheromone ant venom methyl 6-methylsalicylate structure-activity correlation 


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  1. Anslow, W.K., andRaistrick, H. 1931. Studies on the biochemistry of microorganisms XIX 6-hydroxy-2-methylbenzoic acid, a product of the metabolism of glucose byPenicillium griseo-fulvum Dierckx.Biochem. J. 25:39–44.Google Scholar
  2. Attygalle, A.B., andMorgan, E.D. 1983. Trail pheromone of the antTetramorium caespitum (L.).Naturwissenschaften 70:364–365.Google Scholar
  3. Attygalle, A.B., andMorgan, E.D. 1985. Ant trail pheromones.Adv. Insect Physiol. 18:1–30.Google Scholar
  4. Attygalle, A.B., andMorgan, E.D. 1988. Pheromones in nanogram quantities: Structure determination by combined microchemical and gas Chromatographie methods.Angew. Chem. Internat. Ed. English, 27:460–478.Google Scholar
  5. Billen, J.P.J., Evershed, R.P., Attygalle, A.B., Morgan, E.D., andOllett, D.G. 1986. The contents of the Dufour glands of workers of three species ofTetramorium (Hymenoptera: Formicidae).J. Chem. Ecol. 12:669–685.Google Scholar
  6. Brand, J.M., Fales, H.M., Sokoloski, F.A., Macconnell, J.G., Blum, M.S., andDuffield, R.M. 1973. Identification of mellein in the mandibular gland of carpenter ants.Life Sci. 13:201–211.PubMedGoogle Scholar
  7. Evershed, R.P., Morgan, E.D., andCammaerts, M.C. 1982. 3-Ethyl-2,5-dimethylpyrazine, the trail pheromone from the venom gland of eight species ofMyrmica ants.Insect Biochem. 12:383–391.Google Scholar
  8. Gnanasunderam, C., Young, H., andBenn, M.H. 1984. Defensive secretions of New Zealand tenebrionids-III. The identification of methyl esters of 6-methyl and 6-ethylsalicylic acid inChrysopephus expolitus (Coleoptera: Tenebrionidae).Insect Biochem. 14:159–161.Google Scholar
  9. Hauser, P.M., andPogany, S.A. 1980. 2-Hydroxy-6-methylbenzoic acid derivatives.Synth. Commun. 814–815.Google Scholar
  10. Jackson, B.D., Wright, P.J., andMorgan, E.D. 1989. 3-Ethyl-2,5-dimethylpyrazine, a component of the trail pheromone of the antMessor bouvieri.Experientia 45:487–489.Google Scholar
  11. Kannangara, C.G., Henningssen, K.W., Stumpf, P.K., andVon Wettstein, D. 1971. 6-Methylsalicylic acid synthesis by isolated barley chloroplasts.Eur. J. Biochem. 21:334–338.PubMedGoogle Scholar
  12. Kunesch, G., Zagatti, P., Pouvreau, A., andCassini, R. 1987. A fungal metabolite as the male wing gland pheromone of the bumble-bee wax moth,Aphomia sociellaL.Z. Naturforsch. 42c:657–659.Google Scholar
  13. Lloyd, H.A., Schmuff, N.R., andHefetz, A. 1984. Chemistry of the male mandibular gland secretion of the carpenter ant,Camponotus thoracicus fellah Emery.Comp. Biochem. Physiol. B: Comp. Biochem. 78B:687–689.Google Scholar
  14. Morgan, E.D. 1990a. Insect trail pheromones: A perspective of progress, pp. 259–270,in A.R. McCaffrey and I.D. Wilson (eds.). Chromatography and Isolation of Insect Hormones and Pheromones. Plenum Press, New York.Google Scholar
  15. Morgan, E.D. 1990b. Preparation of small scale samples from insects for chromatography.Anal. Chim. Acta. 236:227–235.Google Scholar
  16. Morgan, E.D., andOllett, D.G. 1987. Methyl 6-methylsalicylate, trail pheromone of the antTetramorium impurum.Naturwissenschaften 74:596–597.Google Scholar
  17. Morgan, E.D., andWadhams, L.J. 1972. Gas chromatography of volatile compounds in small samples of biological materials. 7.Chromatogr. Sci. 10:528–529.Google Scholar
  18. Pasteels, J.M., andVerhaeghe, J.C., 1974. Dosage biologique de la phéromone de piste chez les fourrageures et les reines deMyrmica rubra.Insectes Soc. 21:167–180.Google Scholar
  19. Pasteels, J.M., Verhaeghe, J.C., Ottinger, R., Braekman, J.C., andDaloze, D. 1981. Absolute configuration of (3R,4S)-4-methyl-3-hexanol-a pheromone from the head of the antTetramorium impurum Foerster.Insect Biochem. 11:675–678.Google Scholar
  20. Riley, R.G., Silverstein, R.M., Carroll, B., andCarroll, R. 1974. Methyl 4-methylpyrrole-2-carboxylate: A volatile trail pheromone from the leaf-cutting ant,Atta cephalotes.J. Insect Physiol. 20:651–654.PubMedGoogle Scholar
  21. Sexton, W.A. 1963. Chemical Constitution and Biological Activity, 3rd ed. Spon, London, pp. 161–163.Google Scholar
  22. Siegel, S., andCastellan, N.J. 1988. Non-Parametric Statistics for the Behavioural Sciences. McGraw-Hill, Singapore, p. 128.Google Scholar
  23. Sonnet, P.E., andMoser, J.C. 1972. Synthetic analogs of the trail pheromone of the leaf-cutting ant,Atta texana (Buckley).J. Agric. Food Chem. 20:1191–1194.Google Scholar
  24. Sonnet, P.E., andMoser, J.C. 1973. Trail pheromone: Responses of the Texas leaf-cutting ant,Atta texana to selected halo- and cyanopyrrole-2-aldehydes, ketones, and esters.Environ. Entomol. 2:851–854.Google Scholar
  25. Tecle, B., Brophy, J.J., andToia, R.F. 1986. Biosynthesis of 2-hydroxy-6-methylacetophenone in an Australian ponerine ant,Rhytidoponera aciculata (Smith).Insect Biochem. 16:333–336.Google Scholar
  26. Tumlinson, J.H., Moser, J.C., Silverstein, R.M., Brownlee, R.G., andRuth, J.M. 1972. A volatile trail pheromone of the leaf-cutting antAtta texana.J. Insect Physiol. 18:809–814.Google Scholar
  27. Weiss, U., andEdwards, J.M. 1980. The Biosynthesis of Aromatic Compounds, Wiley, New York. pp. 356–358.Google Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • E. David Morgan
    • 1
  • Brian D. Jackson
    • 1
  • David G. Ollett
    • 1
  • Geoffrey W. Sales
    • 1
  1. 1.Department of ChemistryUniversity of KeeleStaffordshireEngland

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