Summary
A combinatorial library containing mixtures of amides and esters was prepared through solid-phase chemistry. The advantages of using solid-phase chemistry over solution-phase chemistry to prepare this library are discussed. The library was screened through a high-throughput whole organism herbicidal assay upon which a mixture containing amides was found to have herbicidal activity. Deconvolution of the mixture providedN-(3-benzoylphenyl)-3-(1,1-dimethylethyl)-1-methyl)-1H-pyrazole-5-carboxamide as a herbicidal lead with broadleaf and narrowleaf pre-emergence herbicidal activity as low as 100 g/ha on some weed species. This study represents the first report of an agrochemical discovered using a combinatorial approach.
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Supplementary Material, comprising experimental procedures for the preparation of resin II and the reaction of II with nucleophiles, GC/MS and LC/MS data for the reaction ofII with morpholine, and a detailed experimental for the preparation of 2 with characterization data, is available upon request.
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Parlow, J.J., Normansell, J.E. Discovery of a herbicidal lead using polymer-bound activated esters in generating a combinatorial library of amides and esters. Mol Divers 1, 266–269 (1996). https://doi.org/10.1007/BF01715531
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DOI: https://doi.org/10.1007/BF01715531