Contributions to ecological chemistry CXII1. Balance of conversion of buturon-14C in wheat under outdoor conditions.

The urea herbicide buturon (N-[p-chlorophenyl]-N'-methyl-N'-isobutinyl-urea), 14C-labeled, was sprayed on winter wheat as an aqueous formulation (2.98 kg/ha) under outdoor conditions. Upon harvest (three months after application), a total of 49.2% of the applied radiocarbon was recovered: 2.0% in the plants, 46.9% in the soil, and 0.3% in the leaching water (depth greater than 50 cm); less than 0.1% was in the grains (0.464 ppm). Only about half of the radioactivity present in plants could be recovered under mild extraction conditions; about half of this was unchanged buturon. In straw and husk extracts, the following metabolites were identified by gaschromatography/mass spectrometry:N-(p-chlorophenyl)-N-methyl-O-methyl-carbamate (metabolite I), N-phenyl-N'-formyl-urea (metabolite II), two unstable metabolites giving (p-chlorophenyl)-isocyanate upon purification (metabolites III and IV), N-(p-chlorophenyl)-N'-methyl-N'-isobutenylol-urea (metabolite V), p-chloroformanilide (metabolite VI) and biologically bound p-chloroaniline (metabolite VII). In the root and basal stem extract, the following metabolites were identified by gas chromatography/mass spectrometry: N-(p-chlorophenyl)-O-methyl-carbamate (metabolite VIII) and N-(p-chlorophenyl)-N'-methyl-urea (metabolite IX).