Inpyrfluxam, 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, is a fungicide to control fungal pathogens in various agriculturally important crops. Inpyrfluxam has one asymmetric carbon atom at 3 position in the cyclopentyl ring, which gives rise to 2 isomers, R and S. The 3R-isomer is the active form of the fungicide and represents about 97% of the total Inpyrfluxam in commercial formulations. A confined rotational crops study was conducted with the 14C-Inpyrfluxam, separately labeled in the phenyl and the pyrazolyl rings. The metabolites of 14C-Inpyrfluxam produced in the rotational crops of sorghum, lettuce and radish included several des-methylation and oxidation products in both free and conjugated forms. These metabolites existed in mixtures of various enantiomeric and diastereomeric forms, which were separated, characterized and quantitated using various analytical techniques. The qualitative and quantitative results of these isomeric metabolites in rotational crops at various planting intervals will be discussed.

Transformation of chiral fungicide Inpyrfluxam to stereoisomeric metabolites in confined rotational crops

256th National Meeting (2018)

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