3-Nitro-1,2,4-triazol-5-one, a less sensitive explosive

Lee, Kien-Yin; Chapman, Lonnie B.; Cobura, Michael D.

doi:10.1080/07370658708012347

Cited by 225 publications

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“…The impact of NTO on the environment has not yet been investigated, and any potential risk can only be accurately predicted when knowledge of its metabolism in mammalian tissues is available. Toxicological studies on NTO indicate that the molecule is not toxic to mice or rats when given orally (LD,,, > 5g/ kg), and is a mild irritant when applied to rabbit skin [7]. However, these investigations did not assess the carcinogenic properties that a molecule having the structure of NTO may possess, based on findings for other nitro-aromatic or nitro-heterocyclic explosives [6,8,91.…”

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confidence: 99%

Metabolism of ¹⁴C‐Labelled 5‐Nitro‐1,2,4‐Triazol‐3‐One by Rat Liver Microsomes Evidence for the Participation of Cytochrome P‐450

Campion

Delaforge²,

Noël

et al. 1997

European Journal of Biochemistry

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In the present study, we synthesized '"C-labelled 5-nitro-l,2,4-triazol-3-one (NTO) and investigated its hepatic metabolism by dexamethasone-induced murine hepatic microsomes. Under the nitrogen atmosphere, 5-amino-l,2,4-triazol-3-one was the only detected metabolite of NTO. The microsomal nitroreductase activity was dependent on NADPH, totally inhibited by carbon monoxide and partially inhibited by oxygen. In aerobic conditions, beside a low amount of amine, the major metabolite formed is the 5-hydroxy-triazolone, urazole. This compound resulted from the oxidative denitrification of NTO, which produced equivalent amount of nitrite. This reaction, like the nitroreductaae activity, was dependent on NADPH and totally inhibited by carbon monoxide. Both nitroreduction and oxidative denitrification were inhibited by imidazole-related inhibitors : miconazole and methimazole, and to a less extent by N-octylamine. The microsomal denitrification was induced by the treatment of rats with dexamethasone and phenobarbital. The microsomal reductare activity is present in untreated rat microsomes, and recovered with various inducers. The results of this study indicate the role played by cytochrome P-450 in the metabolism of NTO, supported by its transformation with reconstituted cytochrome P-450 systems.Keywords: nitrotriazolone; cytochrome P-450; nitroreductase; denitrification; dexamethasone.The explosive 5-nitro-1,2,4-triazol-3-one (NTO) 1 is thermally stable and impact-insensitive [ 11. Its high performance and stability [2, 31 made it of considerable interest to both the defense and civilian sectors. NTO is produced in many countries in multi-ton amounts for large scale formulation and evaluation. Consequently, it is a potential source of pollution in soils and waters around facilities where it is made or used. Several examples of such ecological and health damage caused by explosives in and around military facilities have been reported [4-61. The impact of NTO on the environment has not yet been investigated, and any potential risk can only be accurately predicted when knowledge of its metabolism in mammalian tissues is available. Toxicological studies on NTO indicate that the molecule is not toxic to mice or rats when given orally (LD,,, > 5g/ kg), and is a mild irritant when applied to rabbit skin [7]. However, these investigations did not assess the carcinogenic properties that a molecule having the structure of NTO may possess, based on findings for other nitro-aromatic or nitro-heterocyclic explosives [6,8, 91. Thus, the metabolic intermediates produced during the nitroreduction of nitro compounds cause local damage in the liver [lo]. These intermediates are responsible for the cytotoxicity, neurotoxicity and chemosensitization of 2-nitroimidazole derivatives [II, 121, and for the mutagenicity, genotoxicity and carcinogenicity of nitro aromatic [8, 101 and nitro aliphatic compounds [ 131. Intermediates, including hydroxylamines, ring-opening products and activated oxygen species, are probably responsible for the bi...

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confidence: 99%

Metabolism of ¹⁴C‐Labelled 5‐Nitro‐1,2,4‐Triazol‐3‐One by Rat Liver Microsomes Evidence for the Participation of Cytochrome P‐450

Campion

Delaforge²,

Noël

et al. 1997

European Journal of Biochemistry

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“…5-Nitro-1,2,4-triazol-3-one (NTO) was recently developed as a leader of a new generation of ammunition. It exhibits the same performance as RDX, but a higher stability against physical constraints (such as pressure, heat, impact, and friction) [2,16]. This compound has met with considerable interest from both the defense and civilian sectors.…”

Section: Introductionmentioning

confidence: 98%

Microbial remediation of NTO in aqueous industrial wastes

Campion

1999

FEMS Microbiology Letters

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The bioremediation of aqueous wastes containing 5-nitro-1,2,4-triazol-3-one (NTO) was investigated. The microorganism used is a Bacillus licheniformis strain, isolated from the contaminated solutions by enrichment techniques. The biodegradation was carried out in the waste (15 g l 31 NTO) and proceeded through the nitroreduction of NTO, followed by the ring cleavage of the formed primary amine 5-amino-1,2,4-triazol-3-one (ATO). Both steps were optimized and according to the optimal conditions, the nitroreduction of NTO is total in 24 h, while the degradation of ATO requires 2 weeks of incubation. The end products of the biodegradation were carbon dioxide (40%), urea and a polar compound, assumed to be hydroxyurea. A mechanism of ATO ring cleavage was postulated in the light of experimental data, and led us to propose an overall degradation sequence for NTO. ß

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“…Lee et al [16,17] reported 3-nitro-1,2,4-triazol-5-one (NTO) to be relatively insensitive compared to RDX, with detonation performance comparable to RDX. Cliff et al [18] carried out studies on NTO/TNT 50/50 formulations.…”

Section: Introductionmentioning

confidence: 99%

Studies on NTO-, FOX-7- and DNAN-based Melt Cast Formulations

Mishra¹,

Vadali²,

Bhagat³

et al. 2017

Cent. Eur. J. Energ. Mater.

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Abstract:In the present paper, 2,4-dinitroanisole (DNAN) has been evaluated as a melt cast explosive in comparison to the widely used 2,4,6-trinitrotoluene (TNT). The detonation failure diameter of a bare DNAN charge is greater than 100 mm and about 44 mm with 1.5 mm steel confinement. Comparative studies of two sets of formulations were carried out. The first set comprised formulations containing 60% of NTO, FOX-7, HMX or RDX and 40% of DNAN or TNT. The second set comprised formulations containing 30% of NTO, FOX-7, TATB or RDX and 70% of DNAN or TNT. The studies were mainly concentrated on characterization of the formulations, which included determination of the sensitivity parameters and the velocity of detonation (VOD). The study confirmed that DNAN and DNANbased formulations are relatively insensitive compared to TNT and the analogous TNT-based formulations respectively. The rate of the detonation reaction of DNAN is enhanced in the presence of the high energy ingredients RDX, HMX, FOX-7 and NTO to varying degrees. The VODs of the FOX-7/TNT and RDX/ TNT formulations match closely with the proportions of FOX-7 and RDX under study. The VOD and shock sensitivity of the FOX-7/DNAN formulations decrease rapidly compared to the RDX/DNAN formulations, with increases in the proportion of FOX-7 or RDX. The combinations of NTO with TNT, and NTO with DNAN, are more shock insensitive than TNT or DNAN alone. NTO-based compositions are more insensitive than FOX-7-based compositions.

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3-Nitro-1,2,4-triazol-5-one, a less sensitive explosive

Cited by 225 publications

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Metabolism of ¹⁴C‐Labelled 5‐Nitro‐1,2,4‐Triazol‐3‐One by Rat Liver Microsomes Evidence for the Participation of Cytochrome P‐450

Metabolism of ¹⁴C‐Labelled 5‐Nitro‐1,2,4‐Triazol‐3‐One by Rat Liver Microsomes Evidence for the Participation of Cytochrome P‐450

Microbial remediation of NTO in aqueous industrial wastes

Studies on NTO-, FOX-7- and DNAN-based Melt Cast Formulations

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3-Nitro-1,2,4-triazol-5-one, a less sensitive explosive

Cited by 225 publications

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Metabolism of 14C‐Labelled 5‐Nitro‐1,2,4‐Triazol‐3‐One by Rat Liver Microsomes Evidence for the Participation of Cytochrome P‐450

Metabolism of 14C‐Labelled 5‐Nitro‐1,2,4‐Triazol‐3‐One by Rat Liver Microsomes Evidence for the Participation of Cytochrome P‐450

Microbial remediation of NTO in aqueous industrial wastes

Studies on NTO-, FOX-7- and DNAN-based Melt Cast Formulations

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Metabolism of ¹⁴C‐Labelled 5‐Nitro‐1,2,4‐Triazol‐3‐One by Rat Liver Microsomes Evidence for the Participation of Cytochrome P‐450

Metabolism of ¹⁴C‐Labelled 5‐Nitro‐1,2,4‐Triazol‐3‐One by Rat Liver Microsomes Evidence for the Participation of Cytochrome P‐450