Abstract
2,4-Dinitroanisole (DNAN) is a low sensitive melt-cast chemical being tested by the Military Industry as a replacement for 2,4,6-trinitrotoluene (TNT) in explosive formulations. Little is known about the fate of DNAN and its transformation products in the natural environment. Here we report aerobic biotransformation of DNAN in artificially contaminated soil microcosms. DNAN was completely transformed in 8 days in soil slurries supplemented with carbon and nitrogen sources. DNAN was completely transformed in 34 days in slurries supplemented with carbons alone and persisted in unamended microcosms. A strain of Bacillus (named 13G) that transformed DNAN by co-metabolism was isolated from the soil. HPLC and LC–MS analyses of cell-free and resting cell assays of Bacillus 13G with DNAN showed the formation of 2-amino-4-nitroanisole as the major end-product via the intermediary formation of the arylnitroso (ArNO) and arylhydroxylamino (ArNHOH) derivatives, indicating regioselective reduction of the ortho-nitro group. A series of secondary reactions involving ArNO and ArNHOH gave the corresponding azoxy- and azo-dimers. Acetylated and demethylated products were identified. Overall, this paper provides the evidence of fast DNAN transformation by the indigenous microbial populations of an amended soil with no history of contamination with explosives and a first insight into the aerobic metabolism of DNAN by the soil isolate Bacillus 13G.
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Acknowledgments
We acknowledge Defence Research Development Canada, Department of National Defence, for funding of this project. We thank L. Paquet, A. Corriveau, C. Beaulieu and S. Deschamps for the analytic support. We would like to thank Dr. Arthur Provatas from Defence Science and Technology Organisation (DSTO), Australia, for helpful discussions and for providing us with literature reports on DNAN.
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Perreault, N.N., Manno, D., Halasz, A. et al. Aerobic biotransformation of 2,4-dinitroanisole in soil and soil Bacillus sp.. Biodegradation 23, 287–295 (2012). https://doi.org/10.1007/s10532-011-9508-7
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DOI: https://doi.org/10.1007/s10532-011-9508-7