5-nitro-1-2-4-triazol-3-one and nitroguanidine

5-nitro-1-2-4-triazol-3-one has been researched along with nitroguanidine* in 9 studies

Other Studies

9 other study(ies) available for 5-nitro-1-2-4-triazol-3-one and nitroguanidine

ArticleYear
Photo-transformation of aqueous nitroguanidine and 3-nitro-1,2,4-triazol-5-one: Emerging munitions compounds.
    Chemosphere, 2019, Volume: 228

    Two major components of insensitive munition formulations, nitroguanidine (NQ) and 3-nitro-1,2,4-triazol-5-one (NTO), are highly water soluble and therefore likely to photo-transform while in solution in the environment. The ecotoxicities of NQ and NTO solutions are known to increase with UV exposure, but a detailed accounting of aqueous degradation rates, products, and pathways under different exposure wavelengths is currently lacking. Here, we irradiated aqueous solutions of NQ and NTO over a 32-h period at three ultraviolet wavelengths (254 nm, 300 nm, and 350 nm) and analyzed their degradation rates and transformation products. NQ was completely degraded by 30 min at 254 nm and by 4 h at 300 nm, but it was only 10% degraded after 32 h at 350 nm. Mass recoveries of NQ and its transformation products were ≥80% for all three wavelengths, and consisted of large amounts of guanidine, nitrate, and nitrite, and smaller amounts of cyanamide, cyanoguanidine, urea, and ammonium. NTO degradation was greatest at 300 nm with 3% remaining after 32 h, followed by 254 nm (7% remaining) and 350 nm (20% remaining). Mass recoveries of NTO and its transformation products were high for the first 8 h but decreased to 22-48% by 32 h, with the major aqueous products identified as ammonium, nitrate, nitrite, and a urazole intermediate. Environmental half-lives of NQ and NTO in pure water were estimated as 4 and 6 days, respectively. We propose photo-degradation pathways for NQ and NTO supported by observed and quantified degradation products and changes in solution pH.

    Topics: Environmental Monitoring; Guanidines; Nitro Compounds; Photolysis; Triazoles

2019
Comparative toxicogenomics of three insensitive munitions constituents 2,4-dinitroanisole, nitroguanidine and nitrotriazolone in the soil nematode Caenorhabditis elegans.
    BMC systems biology, 2018, 12-14, Volume: 12, Issue:Suppl 7

    Ecotoxicological studies on the insensitive munitions formulation IMX-101 and its components 2,4-dinitroanisole (DNAN), nitroguanidine (NQ) and nitrotriazolone (NTO) in various organisms showed that DNAN was the main contributor to the overall toxicity of IMX-101 and suggested that the three compounds acted independently. These results motivated this toxicogenomics study to discern toxicological mechanisms for these compounds at the molecular level.. Here we used the soil nematode Caenorhabditis elegans, a well-characterized genomics model, as the test organism and a species-specific, transcriptome-wide 44 K-oligo probe microarray for gene expression analysis. In addition to the control treatment, C. elegans were exposed for 24 h to 6 concentrations of DNAN (1.95-62.5 ppm) or NQ (83-2667 ppm) or 5 concentrations of NTO (187-3000 ppm) with ten replicates per treatment. The nematodes were transferred to a clean environment after exposure. Reproduction endpoints (egg and larvae counts) were measured at three time points (i.e., 24-, 48- and 72-h). Gene expression profiling was performed immediately after 24-h exposure to each chemical at the lowest, medium and highest concentrations plus the control with four replicates per treatment.. Statistical analyses indicated that chemical treatment did not significantly affect nematode reproduction but did induce 2175, 378, and 118 differentially expressed genes (DEGs) in NQ-, DNAN-, and NTO-treated nematodes, respectively. Bioinformatic analysis indicated that the three compounds shared both DEGs and DEG-mapped Reactome pathways. Gene set enrichment analysis further demonstrated that DNAN and NTO significantly altered 12 and 6 KEGG pathways, separately, with three pathways in common. NTO mainly affected carbohydrate, amino acid and xenobiotics metabolism while DNAN disrupted protein processing, ABC transporters and several signal transduction pathways. NQ-induced DEGs were mapped to a wide variety of metabolism, cell cycle, immune system and extracellular matrix organization pathways.. Despite the absence of significant effects on apical reproduction endpoints, DNAN, NTO and NQ caused significant alterations in gene expression and pathways at 1.95 ppm, 187 ppm and 83 ppm, respectively. This study provided supporting evidence that the three chemicals may exert independent toxicity by acting on distinct molecular targets and pathways.

    Topics: Animals; Anisoles; Caenorhabditis elegans; Guanidines; Oligonucleotide Array Sequence Analysis; Risk Assessment; Toxicogenetics; Transcription, Genetic; Transcriptome; Triazoles

2018
The increased toxicity of UV-degraded nitroguanidine and IMX-101 to zebrafish larvae: Evidence implicating oxidative stress.
    Aquatic toxicology (Amsterdam, Netherlands), 2017, Volume: 190

    Insensitive munitions (IMs) improve soldier safety by decreasing sympathetic detonation during training and use in theatre. IMs are being increasingly deployed, although the environmental effects of IM constituents such as nitroguanidine (NQ) and IM mixture formulations such as IMX-101 remain largely unknown. In the present study, we investigated the acute (96h) toxicity of NQ and IMX-101 to zebrafish larvae (21d post-fertilization), both in the parent materials and after the materials had been irradiated with environmentally-relevant levels of ultraviolet (UV) light. The UV-treatment increased the toxicity of NQ by 17-fold (LC50 decreased from 1323mg/L to 77.2mg/L). Similarly, UV-treatment increased the toxicity of IMX-101 by nearly two fold (LC50 decreased from 131.3 to 67.6mg/L). To gain insight into the cause(s) of the observed UV-enhanced toxicity of the IMs, comparative molecular responses to parent and UV-treated IMs were assessed using microarray-based global transcript expression assays. Both gene set enrichment analysis (GSEA) and differential transcript expression analysis coupled with pathway and annotation cluster enrichment were conducted to provide functional interpretations of expression results and hypothetical modes of toxicity. The parent NQ exposure caused significant enrichment of functions related to immune responses and proteasome-mediated protein metabolism occurring primarily at low, sublethal exposure levels (5.5 and 45.6mg/L). Enriched functions in the IMX-101 exposure were indicative of increased xenobiotic metabolism, oxidative stress mitigation, protein degradation, and anti-inflammatory responses, each of which displayed predominantly positive concentration-response relationships. UV-treated NQ had a fundamentally different transcriptomic expression profile relative to parent NQ causing positive concentration-response relationships for genes involved in oxidative-stress mitigation pathways and inhibited expression of multiple cadherins that facilitate zebrafish neurological and retinal development. Transcriptomic profiles were similar between UV-treated versus parent IMX-101 exposures. However, more significant and diverse enrichment as well as greater magnitudes of differential expression for oxidative stress responses were observed in UV-treated IMX-101 exposures. Further, transcriptomics indicated potential for cytokine signaling suppression providing potential connections between oxidative stress and anti-inflammatory re

    Topics: Animals; Anisoles; Dose-Response Relationship, Drug; Gene Expression Profiling; Guanidines; Larva; Nitro Compounds; Oxidative Stress; Transcriptome; Triazoles; Ultraviolet Rays; Water Pollutants, Chemical; Zebrafish

2017
Aquatic toxicity of photo-degraded insensitive munition 101 (IMX-101) constituents.
    Environmental toxicology and chemistry, 2017, Volume: 36, Issue:8

    Insensitive munitions are desirable alternatives to historically used formulations, such as 2,4,6-trinitrotoluene (TNT), because of their so-called insensitivity to unintended detonation. The insensitive munition IMX-101 is a mixture of 2,4-dinitroanisole (DNAN), 3-nitro-1,2,4-triazol-5-one (NTO), and nitroguanidine (NQ). Environmental releases of munitions may be from production wastewaters or training; these munitions may be exposed to ultraviolet (UV) light. Therefore, it is useful to understand the relative toxicity of IMX-101 and its constituents both before and after photodegradation. The intent of the present study was to generate relative hazard information by exposing the standard ecotoxicological model Ceriodaphnia dubia to each insensitive munition constituent individually and to IMX-101 before and after the exposure solution was irradiated in a UV photoreactor. Without photodegradation, DNAN was more toxic (median lethal concentration [LC50] = 43 mg/L) than the other 2 constituents and it contributed predominantly to the toxicity of IMX-101 (LC50 = 206 mg/L) based on toxic units. Toxicity was observed only at high levels of NQ (LC50 = 1174 mg/L) and pH-adjusted NTO (LC50 = 799 mg/L). The toxicity of IMX-101 is lower than literature-reported TNT toxicity. Photodegradation efficiency was greater at lower insensitive munition concentrations. The observed degradation was greatest for NQ (42-99%), which in turn corresponded to the greatest relative increase in toxicity (100-1000-fold). Modest percent of degradation (4-18%) and increases in phototoxicity (2-100-fold) were observed for NTO and DNAN. Photodegraded NQ products were the predominant source of toxicity of photodegraded IMX-101. Future work involves research to enable analytical and computational confirmation of the specific degradation compounds inducing the observed photoenhanced toxicity. Environ Toxicol Chem 2017;36:2050-2057. Published 2017 Wiley Periodicals Inc. on behalf of SETAC. This article is a US government work and, as such, is in the public domain in the United States of America.

    Topics: Animals; Anisoles; Cladocera; Environmental Monitoring; Explosive Agents; Guanidines; Lethal Dose 50; Nitro Compounds; Photolysis; Triazoles; Trinitrotoluene; United States; Water Pollutants, Chemical

2017
Biodegradation of insensitive munition formulations IMX101 and IMX104 in surface soils.
    Journal of industrial microbiology & biotechnology, 2017, Volume: 44, Issue:7

    The biodegradation potential of insensitive munition melt cast formulations IMX101 and IMX104 was investigated in two unamended training range soils under aerobic and anaerobic growth conditions. Changes in community profiles in soil microcosms were monitored via high-throughput 16S rRNA sequencing over the course of the experiments to infer key microbial phylotypes that may be linked to IMX degradation. Complete anaerobic biotransformation occurred for IMX101 and IMX104 constituents 2,4-dinitroanisole (DNAN) and 3-nitro-1,2,4-triazol-5-one during the 30-day incubation period with Camp Shelby (CS) soil. By comparison, soil from Umatilla chemical depot demonstrated incomplete DNAN degradation with reduced transformation rates for both IMX101 and IMX104. Aerobic soil microcosms for both soils demonstrated reduced transformation rates compared to anaerobic degradation for all IMX constituents with DNAN the most susceptible to biotransformation by CS soil. Overall, IMX constituents hexahydro-1,3,5-trinitro-1,3,5-triazine and 1-nitroguanidine did not undergo significant transformation. In CS soil, organisms that have been associated with explosives degradation, namely members of the Burkholderiaceae, Bacillaceae, and Paenibacillaceae phylotypes increased significantly in anaerobic treatments whereas Sphingomonadaceae increased significantly in aerobic treatments. Collectively, these data may be used to populate fate and transport models to provide more accurate estimates for assessing environmental costs associated with release of IMX101 and IMX104.

    Topics: Anisoles; Bacillaceae; Bacillales; Biodegradation, Environmental; Burkholderiaceae; Guanidines; Nitro Compounds; RNA, Ribosomal, 16S; Soil; Soil Microbiology; Sphingomonadaceae; Triazines; Triazoles

2017
A two-stage extraction procedure for insensitive munition (IM) explosive compounds in soils.
    Chemosphere, 2016, Volume: 165

    The Department of Defense (DoD) is developing a new category of insensitive munitions (IMs) that are more resistant to detonation or promulgation from external stimuli than traditional munition formulations. The new explosive constituent compounds are 2,4-dinitroanisole (DNAN), nitroguanidine (NQ), and nitrotriazolone (NTO). The production and use of IM formulations may result in interaction of IM component compounds with soil. The chemical properties of these IM compounds present unique challenges for extraction from environmental matrices such as soil. A two-stage extraction procedure was developed and tested using several soil types amended with known concentrations of IM compounds. This procedure incorporates both an acidified phase and an organic phase to account for the chemical properties of the IM compounds. The method detection limits (MDLs) for all IM compounds in all soil types were <5 mg/kg and met non-regulatory risk-based Regional Screening Level (RSL) criteria for soil proposed by the U.S. Army Public Health Center. At defined environmentally relevant concentrations, the average recovery of each IM compound in each soil type was consistent and greater than 85%. The two-stage extraction method decreased the influence of soil composition on IM compound recovery. UV analysis of NTO established an isosbestic point based on varied pH at a detection wavelength of 341 nm. The two-stage soil extraction method is equally effective for traditional munition compounds, a potentially important point when examining soils exposed to both traditional and insensitive munitions.

    Topics: Anisoles; Explosive Agents; Guanidines; Soil; Soil Pollutants; Triazoles

2016
Analysis of munitions constituents in IMX formulations by HPLC and HPLC-MS.
    Talanta, 2014, Volume: 128

    The use of Insensitive Munitions eXplosives (IMX) is increasing as the Army seeks to replace certain conventional munitions constituents, such as 2,4,6-trinitrotolene (TNT), for improved safety. The IMX formulations are more stable and therefore less prone to accidental detonation while designed to match the performance of legacy materials. Two formulations, IMX 101 and 104 are being investigated as a replacement for TNT in artillery rounds and composition B Army mortars, respectively. The chemical formulations of IMX-101 and 104 are comprised of four constituents;2,4-dinitroanisole (DNAN), 3-nitro-1,2,4-triazol-5-one (NTO), 1-nitroguanidine (NQ), and Hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) which are mixed in various ratios to achieve the desired performance. The current work details the analysis of the IMX constituents by single column HPLC-UV-ESI-MS. Detection limits determined are in agreement with similar HPLC analysis of compounds, ranging from 7 to 9μg/L. Gradient mobile phases are used to allow separation of the 4 target compounds in more complex mixture of other concomitant compounds. Mass spectra are used to confirm analyte identity with chromatographic retention time.

    Topics: Acetonitriles; Anisoles; Chromatography, High Pressure Liquid; Explosive Agents; Gas Chromatography-Mass Spectrometry; Guanidines; Methanol; Nitro Compounds; Reproducibility of Results; Spectrometry, Mass, Electrospray Ionization; Triazines; Triazoles; Trifluoroacetic Acid; Water

2014
Biodegradation of IMX-101 explosive formulation constituents: 2,4-dinitroanisole (DNAN), 3-nitro-1,2,4-triazol-5-one (NTO), and nitroguanidine.
    Journal of hazardous materials, 2014, Sep-15, Volume: 280

    Defense agencies are increasingly using insensitive munitions (IM) in place of explosives such as 2,4,6-trinitrotoluene. In this study simultaneous aerobic degradation of the IMX-101 formulation constituents 2,4-dinitroanisole (DNAN), 3-nitro-1,2,4-triazol-5-one (NTO), and nitroguanidine (NQ) was observed and degradation products were examined. Degradation products over four days of incubation included: nitrourea, 1,2-dihydro-3H-1,2,4-triazol-3-one, and 2,4-dinitrophenol. The enrichment culture maximum specific growth rate of 0.12h(-1) and half saturation constant of 288 mg L(-1) during degradation of IMX-101 as a sole nitrogen source suggest that enrichment culture growth kinetics may closely relate to those of other explosive and nitroaromatic compounds.

    Topics: Anisoles; Biodegradation, Environmental; Culture Techniques; Guanidines; Nitro Compounds; Nitrogen; Toxicity Tests; Triazoles

2014
Dissolution, sorption, and phytoremediation of IMX-101 explosive formulation constituents: 2,4-dinitroanisole (DNAN), 3-nitro-1,2,4-triazol-5-one (NTO), and nitroguanidine.
    Journal of hazardous materials, 2014, Sep-15, Volume: 280

    The insensitive munition, IMX-101 approved for use in the USA, contains 2,4-dinitroanisole (DNAN), 3-nitro-1,2,4-triazol-5-one (NTO), and nitroguanidine (NQ) and is designed to be less sensitive to shock and sympathetic detonation. Given the estimated future use of IMX-101, an understanding of IMX-101 constituent attenuation mechanisms on testing and training ranges is needed. Studies were conducted to determine (1) the rates of IMX-101 fragment dissolution during simulated rainfall, (2) DNAN and NTO soil sorption coefficients, (3) ability of grasses to germinate in and phytoremediate IMX-101 contaminated soil, and (4) effect of the addition of IMX-101 degrading enrichment cultures on phytoremediation. The IMX-101 particles were found to dissolve slowly under simulated rainfall conditions with NQ and NTO dissolving first, leaving DNAN crystals. DNAN and NTO sorption to soils fit Freundlich isotherms and limited desorption was observed. DNAN and NQ were shown to be taken up into the roots and shoots of a mixture of big bluestem grass (Andropogon gerardii), Nash Indiangrass (Sorghastrum nutans), and switchgrass (Panicum virgatum) during phytoremediation of soils contaminated with up to 50 mg kg(-1) IMX-101. Complete degradation of IMX-101 to below detection limits occurred over 225 days. The addition of an IMX-101 degrading enrichment culture to the treatments significantly increased the root and shoot mass.

    Topics: Adsorption; Anisoles; Biodegradation, Environmental; Biotransformation; Germination; Guanidines; Nitro Compounds; Plant Roots; Plant Shoots; Poaceae; Rain; Soil; Triazoles

2014
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