L. Bordeleau, J. Rosen, R. Bartha
May 1, 1972
Citations
1
Influential Citations
48
Citations
Journal
Journal of agricultural and food chemistry
Abstract
In soil, the chloroaniline moieties of certain phenylamide herbicides are liberated by microbial acylamidases, and are subsequently transformed by peroxidases to stable chloroazobenzene residues. The intermediate steps of this transformation were studied by allowing 4-chloroaniline or 3,4-dichloroaniline to react under steady state conditions with peroxidase and H202. The results indicated that the initial attack of peroxidase produced a free chloroanilino radical. Formation of another labile intermediate, chlorophenylhydroxylamine, was detected by the spectrum of its trisodium pentacyanoaminoferroate complex. The obtained results are consistent with a proposed pathway involving the transformation of the chloroanilines by peroxidases to chlorophenylhydroxylamines, with or without involvement of free chloroanilino radjcals. The chlorophenylhydroxylamines spontaneously condense with excess chloroanilines and form chloroazobenzenes. The last step may be indirect and may involve the rapid autoxidation of the respective chlorohydrazobenzene intermediates.