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

Abstract

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.

DOI: 10.1007/BF02751095

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@article{Gagliardo1992SoilTO, title={Soil transformation of 2(3H)-benzoxazolone of rye into phytotoxic 2-amino-3H-phenoxazin-3-one}, author={Ronald W. Gagliardo and William Scott Chilton}, journal={Journal of Chemical Ecology}, year={1992}, volume={18}, pages={1683-1691} }