ArticleJournal of hazardous materials2016
(Bio)transformation of 2,4-dinitroanisole (DNAN) in soils.
Article in Journal of hazardous materials, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
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Who cites it
7 citing papers in PubMed, 58 citations in OpenAlex.
- Predicting the transport of 2,4-dinitroanisole (DNAN) and 3-nitro-1,2,4-triazol-5-one (NTO) in sandy and sandy loam soils.Heliyon · 2022Article
- Degradation of Dissolved RDX, NQ, and DNAN by Cathodic Processes in an Electrochemical Flow-Through Reactor.Journal of environmental chemical engineering · 2022Article
- Metabolism and Photolysis of 2,4-Dinitroanisole in Arabidopsis.Environmental science & technology · 2017Article
- Environmental Fate ofEnvironmental science & technology · 2017Article
- Biodegradation of insensitive munition formulations IMX101 and IMX104 in surface soils.Journal of industrial microbiology & biotechnology · 2017Article
- Biotransformation of 2,4-dinitroanisole by a fungal Penicillium sp.Biodegradation · 2017Article
- Microbial toxicity and characterization of DNAN (bio)transformation product mixtures.Chemosphere · 2016Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
Recent studies have begun to assess the environmental fate and toxicity of 2,4-dinitroanisole (DNAN), an insensitive munition compound of interest to defense agencies. Aerobic and anaerobic DNAN biotransformation in soils was evaluated in this study. Under aerobic conditions, there was little evidence of transformation; most observed removal was attributed to adsorption and subsequent slow chemical reactions. Under anaerobic conditions, DNAN was reductively (bio)transformed and the rate of the transformation was positively correlated with soil organic carbon (OC) up to a threshold of 2.07% OC. H2 addition enhanced the nitroreduction rate compared to endogenous treatments lacking H2. Heat-killed treatments provided rates similar to the endogenous treatment, suggesting that abiotic factors play a role in DNAN reduction. Ten (bio)transformation products were detected by high-resolution mass spectrometry. The proposed transformation pathway involves reduction of DNAN to aromatic amines, with putative reactive nitroso-intermediates coupling with the amines to form azo dimers. Secondary reactions include N-alkyl substitution, O-demethylation (sometimes followed by dehydroxylation), and removal of an N-containing group. Globally, our results suggest that the main reaction DNAN undergoes in anaerobic soils is nitroreduction to 2-methoxy-5-nitroaniline (MENA) and 2,4-diaminoanisole (DAAN), followed by anaerobic coupling reactions yielding azo-dimers. The dimers were subsequently subject to further (bio)transformations.
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Registered trials
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