Nonsterile soil transforms the rye metabolite 2(3H)-benzoxazolone (BOA) into 2-amino-3H-phenoxazin-3-one, which is an order of magnitude more toxic to barnyard grass than benzoxazolone. Benzoxazolone was recovered unchanged from sterile soil. However, o-aminophenol is converted to aminophenoxazinone by both sterile and nonsterile soil in the presence of air. Aminophenoxazinone is probably produced by microbial hydrolysis of benzoxazolone into o-aminophenol, which is oxidized to aminophenoxazinone in both sterile and nonsterile soil. No 2,2'-oxo-1,1'-azobenzene was found in any incubations of soil with benzoxazolone, o-aminophenol, or o-azophenol.