J. Bollag, R. Minard, S. Y. Liu
Feb 1, 1983
Citations
2
Influential Citations
87
Citations
Quality indicators
Journal
Environmental science & technology
Abstract
W The pesticide degradation intermediates 4-chloroaniline, 3,4-dichloroaniline, and 2,6-diethylaniline were examined for their ability to react with various phenolic humus constituents in the presence of a fungal phenol oxidase. An initial indication of a cross-coupling reaction was obtained by color formation. Although anilines alone were not transformed by a phenol oxidase isolated from the fungus Rhizoctonia praticola, they readily cross-linked with phenolic acids or their enzymatic products to form hybrids in the presence of the enzyme. A number of hybrid dimers, trimers, and tetramers were isolated and determined by mass spectrometric analysis. The identities of three hybrid dimers formed from syringic acid coupled with 4-chloroaniline, 3,4-dichloroaniline, or 2,g-diethylaniline and a hybrid tetramer from protocatechuic acid coupled with 2,6-diethylaniline were determined. The formation of the hybrid dimer N-(2,6-diethylphenyl)-2,6dimethoxy-p-benzoquinone imine from a cross-linkage between syringic acid and 2,6-diethylaniline was quantitatively evaluated.