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Structure-activity relationship observations oftrans-trimedlure enantiomers

Journal of Chemical Ecology volume 21, pages 69–79 (1995)Cite this article

Abstract

tert-Butyl 4- (and 5-) chloro-trans-2-methylcyclohexane-1-carboxylate (TML), a mixture of four majortrans and four minorcis isomers, is used as an attractant for detecting and monitoring the male Mediterranean fruit fly (medfly),Ceratitis capitata (Wiedemann). The eight isomers (racemic mixtures) were isolated by HPLC, and their relative attractiveness in the field was determined. A quantitative structure-activity relationship (QSAR) was proposed that related a molecular measurement (Å3) of the TML structure to male medfly captures. More recently, thetrans-TML enantiomers were synthesized in sufficient quantities for field testing. This paper reports the computer-aided molecular modeling, via Chem-X, of thetrans-TML enantiomers and the staggered and superimposed fitting with the most attractive isomer, (1S,2S,4R)-TML-C, to determine common volumes and surface areas from Van der Waals (VdW) maps. Observations of structure-activity relationships (SAR) are reported for the staggered fittings.

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Authors and Affiliations

  1. Insect Chemical Ecology Laboratory, BARC-W, United States Department of Agriculture, Agricultural Research Service, 20705, Beltsville, Maryland

    J. D. Warthen Jr.

  2. Environmental Chemistry Laboratory, BARC-W, United States Department of Agriculture, Agricultural Research Service, 20705, Beltsville, Maryland

    W. F. Schmidt

  3. Insect Attractants, Behavior, and Basic Biology Research Laboratory, United States Department of Agriculture, Agricultural Research Service, 32604, Gainesville, Florida

    R. E. Doolittle

  4. Tropical Fruit & Vegetable Research Laboratory, United States Department of Agriculture, Agricultural Research Service, 96720, Hilo, Hawaii

    R. T. Cunningham

Authors
  1. J. D. Warthen Jr.
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  2. W. F. Schmidt
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  3. R. E. Doolittle
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  4. R. T. Cunningham
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Warthen, J.D., Schmidt, W.F., Doolittle, R.E. et al. Structure-activity relationship observations oftrans-trimedlure enantiomers. J Chem Ecol 21, 69–79 (1995). https://doi.org/10.1007/BF02033663

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  • DOI: https://doi.org/10.1007/BF02033663

Key Words

  • Insecta
  • Ceratitus capitata
  • medfly
  • trimedlure
  • enantiomer
  • attractant
  • lure
  • SAR
  • VdW
  • Chem-X