Abstract
Volatiles from lesser grain borers,Rhyzopertha dominica (F.) (Coleoptera: Bostrichidae), were collected on Porapak Q, and those from the male beetles were shown to contain two compounds, that were attractive individually and in combination to both sexes. These compounds were identified as (S)-(+)-1-methylbutyl (E)-2-methyl-2-pentenoate and (S)-(+)-1-methylbutyl (E)-2,4-dimethyl-2-pentenoate by spectrometry and comparison with synthesized compounds. The two compounds have been assigned the trivial names dominicalure 1 and dominicalure 2, respectively. Synthesized samples of these compounds, individually and in combination, were effective in trapping both sexes in field studies.
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Batrakov, S.G., andBergel'son, L.D. 1964. Unsaturated acids and macrocyclic lactones. XIV. Configuration ofmeso-2,4-dimethyl-1,3,5-pentanetriol and of the asymmetric center at C3 in erythromycin and oleanomycin.Izv. Akad. Nauk. SSSR, Ser. Khim. 9:1640–1648.
Burkholder, W.E. 1970. Pheromone research with stored product Coleoptera, p. 19,in D.L. Wood, R.M. Silverstein, and M. Nakajima (eds.). Control of Insect Behavior by Natural Products. Academic Press, New York.
Burkholder, W.E. 1976. Application of pheromones for manipulating insect pests of stored products, p. 111,in T. Kono and S. Ishii (eds.). Proceedings of the Symposium on Insect Pheromones and Their Applications. Nagaoka, Tokyo.
Brownlee, R.G., andSilverstein, R.M. 1968. A micro-preparative gas chromatograph and a modified carbon skeleton determinator.Anal. Chem. 40:2077–2079.
Chan, K.C., Jewell, R.A., Nutting, W.H., andRapoport, H. 1968 The synthesis and stereochemical assignment ofcis- andtrans-2-methyl-2-pentenoic acid and the corresponding esters, aldehydes, and alcohols.J. Org. Chem. 33:3382–3385.
Cross, J.H., Byler, R.C., Cassidy, R.F., Silverstein, R.M., Greenblatt, R.E., Burkholder, W.E., Levinson, A.R., andLevinson, H.Z. 1976 Porapak-Q collection of pheromone components and isolation of (Z)- and (E)-14-methyl-8-hexadecenal, potent sex attraction components from the females of four species ofTrogoderma (Coleoptera: Dermestidae).J. Chem. Ecol. 2:457–468.
Khorramshahi, A., andBurkholder, W.E. 1981. Behavior of the lesser grain borerRhyzopertha dominica (Coleoptera: Bostrichidae): Male produced aggregation pheromone attracts both sexes.J. Chem. Ecol. 7:33–38.
Lucas, H.J., andPrater, A.N. 1937. The isomeric 2-pentenes.J. Am. Chem. Soc. 59:1682–1686.
Mori, K. 1975. Synthesis of optically active forms of sulcatol, the aggregation pheromone in the scolytid beetleGnathotricus sulcatus.Tetrahedron 31:3011–3012.
Ravid, U., Silverstein, R.M., andSmith, L.R. 1978. Synthesis of the enantiomers of 4-substituted γ-lactones with known absolute configuration.Tetrahedron 34:1449–1452.
Smith, L.R., andWilliams, H.J. 1979. Glutamic acid in pheromone synthesis, a useful chiral synthon.J. Chem. Educ. 56:696–698.
Steel, R.G. andTorrie, J.H. 1960. Principles and Procedures of Statistics, 481 pp. McGraw-Hill, New York.
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Approved as TA-14927 by the director of the Texas Agricultural Experiment Station in cooperation with the USDA-FR-SEA.
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Williams, H.J., Silverstein, R.M., Burkholder, W.E. et al. Dominicalure 1 and 2: Components of aggregation pheromone from male lesser grain borerRhyzopertha dominica (F.) (Coleoptera: Bostrichidae). J Chem Ecol 7, 759–780 (1981). https://doi.org/10.1007/BF00990308
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DOI: https://doi.org/10.1007/BF00990308