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Appl. Environ. Microbiol., Sep 1995, 3282-3287, Vol 61, No. 9
Copyright © 1995, American Society for Microbiology

Reduction of Nitrated Diphenylamine Derivatives under Anaerobic Conditions

O Drzyzga, A Schmidt and K Blotevogel
Fachbereich Biologie, AG Mikrobiologie/Rustungsaltlasten, and Fachbereich Chemie, Carl von Ossietzky-Universitat Oldenburg, D-26111 Oldenburg, Germany

2-Nitrodiphenylamine, 4-nitrodiphenylamine, and 2,4-dinitrodiphenylamine were anaerobically metabolized in sediment-water batch enrichments inoculated with mud from the German North Sea coast. The first intermediate in 2,4-dinitrodiphenylamine degradation was 2-amino-4-nitrodiphenylamine, which appeared in large (nearly stoichiometric) amounts before being completely reduced to 2,4-diaminodiphenylamine. Of the second theoretically expected metabolite, 4-amino-2-nitrodiphenylamine, only traces were detected by gas chromatographic-mass spectrometric analysis in highly concentrated extracts. In addition, low levels of 4-nitrodiphenylamine, which may be the product of ortho deamination of intermediately produced 2-amino-4-nitrodiphenylamine, were observed. 2-Nitrodiphenylamine and 4-nitrodiphenylamine were primarily reduced to 2-aminodiphenylamine and 4-aminodiphenylamine, respectively. Diphenylamine was never detected in any experiment as a theoretically possible intermediate. Results from studies with dense cell suspensions of anaerobic, aromatic-compound-mineralizing bacteria confirmed the transformation reactions, which were carried out by microorganisms indigenous to the anaerobic coastal water sediment.

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