Soil transformation of 2(3H)-benzoxazolone of rye into phytotoxic 2-amino-3H-phenoxazin-3-one

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 intoo-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, oro-azophenol.