Abstract
GC-MS analysis of volatiles released from wheat infested with a high density of aphids showed the presence of 6-methyl-5-hepten-2-ol (sulcatol). The proportion of enantiomers present in the volatiles was determined by esterifying the mixture with (1S)-( − )-camphanic chloride and quantifying the esters. The mixture consisted of 75% (R)-( − ) and 25% (S)-( + ). The mixture of enantiomers as well as the racemate showed significant repellency towards apterous Rhopalosiphum padi in an olfactometer (15.7% and 14.4%, respectively, with 10 ng of stimulus). Single enantiomers or a mixture containing 25% (R)-( − )- and 75% (S)-( + )-enantiomers were inactive. The results are discussed in relation to the achievement of specificity by aphids in different pheromone-mediated behaviors.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
BaeckstrÖm, P. 1996. Choice of gradients for minimizing adsorbent consumption in preparative liquid chromatography, pp. 122–136, in International Foundation for Science (IFS) 1996, Techniques in Plant-Insect Interactions and Biopesticides. Proceedings of an IFS Workshop, IFS, Sweden.
Belan, A., Bolte, J., Fauve, A., Gourcy, J. G., and Veschambre, H. 1987. Use of biological systems for the preparation of chiral molecules. 3. An application in pheromone synthesis: Preparation of sulcatol enantiomers. J. Org. Chem. 52:256–260.
Blight, M. 1990. Techniques for isolation and characterisation of volatile semiochemicals of phytophagous insects, pp. 281–288, in A. R. McCaffery and I. D. Wilson (eds.). Chromatography and Isolation of Insect Hormones and Pheromones. Plenum Press, New York.
Borden, J. H., Chonh, L., McLean, J. A., Slessor, K. N., and Mori, K. 1976. Gnathotrichus sulcatus: Synergistic response to enantiomers of the aggregation pheromone sulcatol. Science 192:894–896.
Borden, J. H., Handley, J. R., McLean, S. A., Silverstein, R. M., Chong, L., Slessor, K. N., Johnston, B. D., and Schuler, H. R. 1980. Enantiomer-based specificity in pheromone communication by two sympatric Gnathotrichus species (Coleoptera: Scolytidae). J. Chem. Ecol. 6:445–455.
Bowers, W. S., Nault, L. R., Webb, R. E., and Dutky, S. R. 1972. Aphid alarm pheromone: Isolation, identification, synthesis. Science 177:1121–1122.
Byrne, K. J., Swigar, A. A., Silverstein, R. M., Borden, J. H., and Stokkink, E. 1974. Sulcatol: Population aggregation pheromone in the scolytid beetle, Gnathotrichus sulcatus. J. Insect. Physiol. 20:1895–1900.
Camacho, A. D., Pierce, H. D., and Borden, J. J. 1993. Geometrical and optical isomerism of pheromones in two sympatric Dryocoetes species (Coleoptera: Scolytidae), mediates species specificity and response level. J. Chem. Ecol. 19:2169–2182.
Campbell, C. A. M., Pettersson, J., Pickett, J. A., Wadhams, L. J., and Woodcock, C. M. 1993. Spring migration of damson-hop aphid Phorodon humuli (Homoptera, Aphididae), and summer host plant-derived semiochemicals released on feeding. J. Chem. Ecol. 19:1569–1576.
Dawson, G. W., Griffiths, D. C., Merrit, L. A., Mudd, A., Pickett, J. A., Wadhams, L. J., and Woodcock, C. M. 1990. Aphid semiochemicals—a review, and recent advances on the sex pheromone. J. Chem. Ecol. 16:3019–3030.
Dickens, J. C., and Mori, K. 1989. Receptor chirality and behavioral specificity of the boll weevil, Anthonomus grandis Both. (Coleoptera: Curculionidae), for its pheromone, (+)-grandisol. J. Chem. Ecol. 15:517–528.
Edwards, L. J., Siddall, J. B., Dunham, L. L., Uden, P., and Rislow, C. J. 1973. trans-β-Farnesene, alarm pheromone of the green peach aphid, Myzus persicae (Sulzer). Nature 241:126–127.
Guldemond, J. A., Dixon, A. F. G., Pickett, J. A., Wadhams, L. J., and Woodcok, C. M. 1993. Specificity of sex pheromones, the role of host plant odour in the olfactory attraction of males, and mate recognition in the aphid Cryptomyzus. Physiol. Entomol. 18:137–143.
Hurlbert, S. H. 1984. Pseudoreplication and the design of ecological field experiments. Ecol. Monogr. 54:187–211.
Johnston, B. D., and Slessor, K. N. 1979. Facile syntheses of the enantiomers of sulcatol. Can. J. Chem. 57:233–235.
LÖfstedt, C. 1991. Evolution of moth pheromones, pp. 57–73. in I. Hrdý (ed.). Insect Chemical Ecology. Academia Praha, Prague.
Millar, J. G., Pierce, H. D., Pierce, A. M., Oehlschlager, A. C., and Borden, J. J. 1985. Aggregation pheromones of the grain beetle, Crytolestes turcicus (Coleoptera: Cucujidae). J. Chem. Ecol. 11:1071–1081.
Mori, K. 1981. A simple synthesis of (S)-(+)-sulcatol, the pheromone of Gnathotrichus restesus, employing baker's yeast for asymmetrical reduction. Tetrahedron 37:1341–1342.
Mori, K. 1989. Synthesis of optically active pheromones. Tetrahedron 45:3233–3298.
Oehlschlager, A. C., King, G. G. S., Pierce, H. D., Pierce, A. M., Slessor, K. N., Millar, J. G., and Borden, J. H. 1987. Chirality of macrolide pheromones of grain beetles in the genera Oryzaephilus and Cryptolestes and its implications for species specificity. J. Chem. Ecol. 13:1543–1554.
Oehlschlager, A. C., Pierce, A. M., Pierce, H. D., and Borden, J. H. 1988. Chemical communication in cucujid grain beetles. J. Chem. Ecol. 14:2071–2098.
Pettersson, J., Pickett, J. A., Pye, B. J., Quiroz, A., Wadhams, L. J., and Woodcock, C. M. 1994. Winter host component reduces colonization by bird-cherry-oat aphid Rhopalosiphum padi (L.) (Homoptera, Aphididae), and other aphids in cereal fields. J. Chem. Ecol. 20:2565–2574.
Pettersson, J., Quiroz, A., Stephansson, D., and Niemeyer, H. M. 1995. Odour communication of Rhopalosiphum padi on grasses. Entomol. Exp. Appl. 76:325–328.
Pickett, J. A., Wadhams, L. J., and Woodcock, C. M. 1992. The chemical ecology of aphids. Annu. Rev. Entomol. 37:67–90.
Pierce, A. M., Pierce, H. D., Oehlschlager, A. C., Czyzewska, E., and Borden, J. H. 1987. Influence of pheromone chirality on response by Oryzaephilus surinamensis and Oryzaephilus mercator (Coleoptera: Cucujidae). J. Chem. Ecol. 13:1525–1542.
Plummer, E. L., Stewart, T. E., Byrne, K., Pearce, G. T., and Silverstein, R. M. J. 1976. Determination of the enantiomeric composition of several insect pheromone alcohols. J. Chem. Ecol. 2:307–331.
Quiroz, A., Petterson, J., Pickett, J. A., Wadhams, L. J., and Niemeyer, H. M. 1997. Semiochemicals mediating spacing behavior of bird cherry-oat aphid, Rhopalosiphum padi feeding on cereals. J. Chem. Ecol. 23:2599–2607.
Schuler, H. R., and Slessor, K. N. 1977. Synthesis of enantiomers of sulcatol. Can. J. Chem. 55:3280–3287.
Seybold, S. J. 1993. Role of chirality in olfactory-directed behavior: Aggregation of pine engraver beetles in the genus Ips (Coleoptera: Scolytidae). J. Chem. Ecol. 19:1809–1831.
Silverstein, R. M. 1984. Chemistry of insect communication, pp. 105–121, in T. Lewis (ed.). Insect Communication. 12th Symposium of the Royal Entomological Society of London. Academic Press, London.
TengÖ, J., Ågren, L., Baur, B., Isaksson, R., Liljefors, T., Mori, K., KÖnig, W., and Francke, W. 1990. Andrena wilkella Male bees discriminate between enantiomers of cephalic secretion components. J. Chem. Ecol. 16:429–441.
Thieme, T., and Dixon, A. F. G. 1996. Mate recognition in the Aphid fabae complex: Daily rhythm of release and specificity of sex pheromone. Entomol. Exp. Appl. 79:85–89.
Zadoks, J. C., Chang, T. T., and Konzak, C. F. 1974. A decimal code for the growth stages of cereals. Weed Res. 14:15–21.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Quiroz, A., Niemeyer, H.M. Activity of Enantiomers of Sulcatol on Apterae of Rhopalosiphum padi . J Chem Ecol 24, 361–370 (1998). https://doi.org/10.1023/A:1022540727070
Issue Date:
DOI: https://doi.org/10.1023/A:1022540727070