Herbicide Metabolism: N -Glycoside of Amiben Isolated from Soybean Plants

The N-glycoside of the herbicide 3-amino-2, 5-dichlorobenzoic acid (amiben) was synthesized in the laboratory. The compound was chromatographically identical with a conjugate of amiben isolated from soybean plants, Glycine Max (L.) Merr. The seeds of a tolerant plant, soybean, and of a susceptible one, barley (Hordeum vulgare L.), were incubated in amiben labeled with carbon-14, and the seedlings were extracted. Essentially all the radioactivity in soybean was present as a compound corresponding to N-glycosyl amiben. Only a small amount of this conjugate was present in barley; most of the radioactivity was present as free amiben or as other unidentified metabolites.