HYDROXYLATION OF MONOCHLOROANILINE PESTICIDE-RESIDUES BY FUSARIUM-OXYSPORUM SCHLECHT

Metabolism of 2-, 3-, and 4-chloroanilines by isolated cultures of the soil fungus Fusarium oxysporum Schlecht, and chlorpropham in soil was investigated. Hydroxylated (phenolic) products were detected colorimetrically, extracted, and characterized by thin-layer and gas chromatography and mass spectrometry. The presence of ortho-hydroxylated chloroanilines in F. oxysporum culture solutions was established by a characteristic ortho-elimination process which resulted in the formation of chlorinated benzoxazolines during mass spectral analysis of acylated derivatives. 2-Amino-4-chlorophenol and 2-amino-5-chlorophenol were positively identified as metabolites of 3-and 4-chloroaniline, respectively, in F. oxysporum culture solutions by comparison of the mass fragmentation pattern with acylated reference standards. Chloroaminophenols were also detected as metabolites of 2-chloroaniline in F. oxysporum culture solutions and from chlorpropham-treated soil. © 1979, American Chemical Society. All rights reserved.