bromoxynil
4-hydroxy-3,5-dibromobenzonitrile
Identification
| Name | bromoxynil |
| IUPAC | 3,5-dibromo-4-hydroxybenzonitrile |
| CAS Number | 1689-84-5 |
| EINECS | 216-882-7 |
| FDA UNII | J46EK95K0P |
| Molecular Formula | C7 H3 Br2 N O |
| Molecular Weight | 276.91511000 |
| MDL Number | MFCD00002153 |
| Nikkaji Number | J7.557D |
| Beilstein | 2364039 |
Regulatory
Physical Properties
| Appearance | colorless solid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 190.00 °C. @ 760.00 mm Hg |
| Soluble in | water, 130 mg/L @ 25 °C (exp) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | oral-bird - wild LD50 50 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 3660 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02212']
Safety in Use
| Category | herbicides / pesticides |
| Recommendation for bromoxynil usage levels up to | not for fragrance use. |
| Recommendation for bromoxynil flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
benzonitrile, 3,5-dibromo-4-hydroxy-
brittox
brominal
brominal plus
brominal triple
brominex
brominil
bromotril
bromoxynil phenol
buctril
butil chlorofos
butilchorofos
certrol B
chipco buctril
chipco crab-kleen
4-
cyano-2,6-dibromophenol
2,6-
dibromo-4-cyanophenol
3,5-
dibromo-4-hydroxybenzonitril (ACN)
3,5-
dibromo-4-hydroxybenzonitrile
3,5-
dibromo-4-hydroxyphenyl cyanide
3,5-
dibromo-4-hydroxyphenylcyanide
4-
hydroxy-3,5-dibromobenzonitrile
labuctril 25
litarol M
M&B 10731
novacorn
oxytril M
pardner
sabre
terset
toplan
PubMed:
2-Methyl-4-chlorophenoxyacetic acid and bromoxynil herbicide death.
PubMed:
Synthesis and evaluation of heterocyclic analogues of bromoxynil.
PubMed:
An essential esterase (BroH) for the mineralization of bromoxynil octanoate by a natural consortium of Sphingopyxis sp. strain OB-3 and Comamonas sp. strain 7D-2.
PubMed:
[Induction cell damage and change of nuclear factor-kappa B expression by bromoxynil in SH-SY5Y cells].
PubMed:
A bentazone-resistant mutant of cyanobacterium, Synechococcus elongatus PCC7942 adapts different strategies to counteract on bromoxynil- and salt-mediated oxidative stress.
PubMed:
Photodegradation routes of the herbicide bromoxynil in solution and sorbed on silica nanoparticles.
PubMed:
Further electrophysiological studies on cellular effect of herbicide, bromoxynil, using characean cells.
PubMed:
Use of a potentiometric vital dye to determine the effect of the herbicide bromoxynil octanoate on mitochondrial bioenenergetics in Chlamydomonas reinhardtii.
PubMed:
Bromoxynil residues and dissipation rates in maize crops and soil.
PubMed:
Degradation of bromoxynil octanoate by strain Acinetobacter sp. XB2 isolated from contaminated soil.
PubMed:
[Intervention effect of dimercaptopropansulfonate sodium on central toxic induced by bromoxynil in vivo].
PubMed:
Unique cellular effect of the herbicide bromoxynil revealed by electrophysiological studies using characean cells.
PubMed:
Degradation of three benzonitrile herbicides by Aminobacter MSH1 versus soil microbial communities: pathways and kinetics.
PubMed:
Molecular mechanisms of herbicide-inducible gene expression of tobacco CYP71AH11 metabolizing the herbicide chlorotoluron.
PubMed:
Degradation of bromoxynil and trifluralin in natural water by direct photolysis and UV plus H(2)O(2) advanced oxidation process.
PubMed:
Photosensitized degradation in water of the phenolic pesticides bromoxynil and dichlorophen in the presence of riboflavin, as a model of their natural photodecomposition in the environment.
PubMed:
[Effect of bromoxynil on membrane potential and respiratory control rate in isolated mitochondria from mice liver and intervention effect of NAC].
PubMed:
Bromoxynil degradation in a Mississippi silt loam soil.
PubMed:
Determination of bromoxynil octanoate in soil and corn by GC with electron capture and mass spectrometry detection under field conditions.
PubMed:
Primary effect of bromoxynil to induce plant cell death may be cytosol acidification.
PubMed:
The application of the herbicide bromoxynil to a model soil-derived bacterial community: impact on degradation and community structure.
PubMed:
Dehalogenation of the herbicides bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) and ioxynil (3,5-diiodino-4-hydroxybenzonitrile) by Desulfitobacterium chlororespirans.
PubMed:
Exposure of ground-rig applicators to the herbicide bromoxynil applied as a 1:1 mixture of butyrate and octanoate.
PubMed:
The degradation of the herbicide bromoxynil and its impact on bacterial diversity in a top soil.
PubMed:
Body mass index and bromoxynil exposure in a sample of rural residents during spring herbicide application.
PubMed:
Factors associated with detection of bromoxynil in a sample of rural residents.
PubMed:
Biodegradation of the herbicide bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) by purified pentachlorophenol hydroxylase and whole cells of Flavobacterium sp. strain ATCC 39723 is accompanied by cyanogenesis.
PubMed:
Developmental toxicity of bromoxynil in mice and rats.
PubMed:
Antinuclear antibodies and bromoxynil exposure in a rural sample.
PubMed:
Metabolism of the herbicide bromoxynil by Klebsiella pneumoniae subsp. ozaenae.
PubMed:
Short- and long-term response of sunflower to airborne bromoxynil-octanoate under controlled and field conditions.
PubMed:
Demonstrating formation of potentially persistent transformation products from the herbicides bromoxynil and ioxynil using liquid chromatography-tandem mass spectrometry (LC-MS/MS).
PubMed:
Degradation of ioxynil and bromoxynil as measured by a modified spectrophotometric method.
PubMed:
Enzymic degradation of bromoxynil by cell-free extracts of Streptomyces felleus.
PubMed:
Cloning and expression in Escherichia coli of a Klebsiella ozaenae plasmid-borne gene encoding a nitrilase specific for the herbicide bromoxynil.
PubMed:
Development of an immunochromatographic assay for the rapid detection of bromoxynil in water.
PubMed:
Flow injection spectrophotometric determination of bromoxynil herbicide by diazotization method.
PubMed:
Development of an ELISA for the detection of bromoxynil in water.
PubMed:
Purification and properties of a nitrilase specific for the herbicide bromoxynil and corresponding nucleotide sequence analysis of the bxn gene.
PubMed:
Probing the quinone binding site of photosystem II from Thermosynechococcus elongatus containing either PsbA1 or PsbA3 as the D1 protein through the binding characteristics of herbicides.
PubMed:
Effects of 3,5-Dibromo-4-Hydroxybenzonitrile (Bromoxynil) on Bioenergetics of Higher Plant Mitochondria (Pisum sativum).
PubMed:
Microbial degradation of the benzonitrile herbicides dichlobenil, bromoxynil and ioxynil in soil and subsurface environments--insights into degradation pathways, persistent metabolites and involved degrader organisms.
PubMed:
Substrate selectivity and conformational space available to bromoxynil and acrylonitrile in iron nitrile hydratase.
PubMed:
Bacterial degradation of the herbicide bromoxynil by Agrobacterium radiobacter in biofilm.
PubMed:
Degradation of the herbicide bromoxynil in Pseudomonas putida.
PubMed:
HPLC measurement of chlorophenoxy herbicides, bromoxynil, and ioxynil, in biological specimens to aid diagnosis of acute poisoning.
PubMed:
Impact of an herbicide combination of bromoxynil and prosulfuron on soil microorganisms.
PubMed:
Chemiluminescent determination of the pesticide bromoxynil by on-line photodegradation in a flow-injection system.
PubMed:
Semi-permeable surface analytical reversed-phase column for the improved trace analysis of acidic pesticides in water with coupled-column reversed-phase liquid chromatography with UV detection. Determination of bromoxynil and bentazone in surface water.
PubMed:
Effect of airborne bromoxynil-octanoate and metribuzin on non-target plants.
PubMed:
Molecular characterization of the enzymes involved in the degradation of a brominated aromatic herbicide.
PubMed:
Axial skeletal and Hox expression domain alterations induced by retinoic acid, valproic acid, and bromoxynil during murine development.
PubMed:
Effect of glucose and ribose on microbial degradation of the herbicide bromoxynil continuously added to soil.
PubMed:
[Results of the toxicokinetics of bromoxynil in rats].
PubMed:
Environmental concentrations of agricultural herbicides in Saskatchewan, Canada: bromoxynil, dicamba, diclofop, MCPA, and trifluralin.
PubMed:
[First aid and nursing on acute severe bromoxynil poisoning].
PubMed:
EPA ban on bromoxynil undercuts Calgene's transgenic cotton.
PubMed:
[Experimental study on toxicity and changes of biochemical indicator in acute bromoxynil poisoning].
PubMed:
[Study on clinical treatment of acute bromoxynil poisoning].
PubMed:
[Investigation on an accident of death induced by bromoxynil poisoning].
PubMed:
Simultaneous extraction and detection of residues of (2,4-dichlorophenoxy)acetic acid and bromoxynil from wheat.
PubMed:
Biotransformation of benzonitrile herbicides via the nitrile hydratase-amidase pathway in rhodococci.
PubMed:
Analysis of airborne pesticides from different chemical classes adsorbed on Radiello® Tenax® passive tubes by thermal-desorption-GC/MS.
PubMed:
Study of Cytotoxic Effects of Benzonitrile Pesticides.
PubMed:
Comparison of liquid and gas chromatography for the determination of bromoxynil octanoate and benzoylprop ethyl in wheat products.
PubMed:
The in vitro degradation of the herbicide bromoxynil.
PubMed:
Fate of the herbicides bromoxynil and casoron in cows.
PubMed:
Kinetics and mechanism of the degradation of two pesticides in aqueous solutions by ozonation.
PubMed:
Hydrolysis of benzonitrile herbicides by soil actinobacteria and metabolite toxicity.
PubMed:
Dissipation of six acid herbicides in water and sediment of two Canadian prairie wetlands.
PubMed:
Metabolism of agrochemicals and related environmental chemicals based on cytochrome P450s in mammals and plants.
PubMed:
Biotransformation of 3,5-dibromo-4-hydroxybenzonitrile under denitrifying, Fe(III)-reducing, sulfidogenic, and methanogenic conditions.
PubMed:
Exposure to herbicides in house dust and risk of childhood acute lymphoblastic leukemia.
PubMed:
Effects of a herbicide mixture on primary and bacterial productivity in four prairie wetlands with varying salinities: an enclosure approach.
PubMed:
Enchytraeidae Fridericia bulbosa as a new test species for soil ecotoxicity assessment.
PubMed:
Oxidation kinetics of two pesticides in natural waters by ozonation and ozone combined with hydrogen peroxide.
PubMed:
Determination and occurrence of phenoxyacetic acid herbicides and their transformation products in groundwater using ultra high performance liquid chromatography coupled to tandem mass spectrometry.
PubMed:
Long-range interaction between the Mn4CaO5 cluster and the non-heme iron center in photosystem II as revealed by FTIR spectroelectrochemistry.
PubMed:
Structures and binding sites of phenolic herbicides in the Q(B) pocket of photosystem II.
PubMed:
Residential agricultural pesticide exposures and risk of neural tube defects and orofacial clefts among offspring in the San Joaquin Valley of California.
PubMed:
How does the QB site influence propagate to the QA site in photosystem II?
PubMed:
Pleiotropic effects of herbicide-resistance genes on crop yield: a review.
PubMed:
A comparative study of nitrilases identified by genome mining.
PubMed:
Autodisplay of nitrilase from Klebsiella pneumoniae and whole-cell degradation of oxynil herbicides and related compounds.
PubMed:
Herbicide effect on the photodamage process of photosystem II: fourier transform infrared study.
PubMed:
Energetics in photosystem II from Thermosynechococcus elongatus with a D1 protein encoded by either the psbA1 or psbA3 gene.
PubMed:
Effects of herbicide mixture on microbial communities in prairie wetland ecosystems: a whole wetland approach.
PubMed:
Herbicide-induced changes in charge recombination and redox potential of Q(A) in the T4 mutant of Blastochloris viridis.
PubMed:
pH-dependence of pesticide adsorption by wheat-residue-derived black carbon.
PubMed:
Halogenated pesticide transformation by a laccase-mediator system.
PubMed:
Effects of glyphosate and two herbicide mixtures on microbial communities in prairie wetland ecosystems: a mesocosm approach.
PubMed:
Occurrence of glyphosate and acidic herbicides in select urban rivers and streams in Canada, 2007.
PubMed:
Simultaneous analysis of pesticides from different chemical classes by using a derivatisation step and gas chromatography-mass spectrometry.
PubMed:
Abiotic degradation of halobenzonitriles: investigation of the photolysis in solution.
PubMed:
Significance of supernumerary ribs in rodent developmental toxicity studies: postnatal persistence in rats and mice.
PubMed:
Recovery of non-target plants affected by airborne herbicides.
PubMed:
The impact of altered herbicide residues in transgenic herbicide-resistant crops on standard setting for herbicide residues.
PubMed:
Effects on aquatic and human health due to large scale bioenergy crop expansion.
PubMed:
Herbicide effect on the hydrogen-bonding interaction of the primary quinone electron acceptor QA in photosystem II as studied by Fourier transform infrared spectroscopy.
PubMed:
Herbicide resistance in transgenic plants expressing a bacterial detoxification gene.
PubMed:
Comparing effects of low levels of herbicides on greenhouse- and field-grown potatoes (Solanum tuberosum L.), soybeans (Glycine max L.), and peas (Pisum sativum L.).
PubMed:
Protection by isoprene against singlet oxygen in leaves.
PubMed:
OH radical reactivity of pesticides adsorbed on aerosol materials: first results of experiments with filter samples.
PubMed:
Atmospheric concentrations and dry and wet deposits of some herbicides currently used on the Canadian Prairies.
PubMed:
Herbicidal treatments for control of Papaver somniferum L.
PubMed:
Influence of pH on pesticide sorption by soil containing wheat residue-derived char.
PubMed:
Interactions of halogenated industrial chemicals with transthyretin and effects on thyroid hormone levels in vivo.
PubMed:
Analysis of trace levels of pesticides in rainwater by SPME and GC-tandem mass spectrometry after derivatisation with PFBBr.
PubMed:
Importance of surface diffusivities in pesticide adsorption kinetics onto granular versus powdered activated carbon: experimental determination and modeling.
PubMed:
High-performance liquid chromatographic study of the aromatic nitrile metabolism in soil bacteria.
PubMed:
Tissue-binding and toxicity of compounds structurally related to the herbicide dichlobenil in the mouse olfactory mucosa.
PubMed:
Liquid chromatography with post-column reagent addition of ammonia in methanol coupled to negative ion electrospray ionization tandem mass spectrometry for determination of phenoxyacid herbicides and their degradation products in surface water.
PubMed:
Imaging plant cell death: GFP-Nit1 aggregation marks an early step of wound and herbicide induced cell death.
PubMed:
Crosstalk and differential response to abiotic and biotic stressors reflected at the transcriptional level of effector genes from secondary metabolism.
PubMed:
Spatially resolved quantification of agrochemicals on plant surfaces using energy dispersive X-ray microanalysis.
PubMed:
Utility of delayed fluorescence as endpoint for rapid estimation of effect concentration on the green alga Pseudokirchneriella subcapitata.
PubMed:
psbA mutation (Asn266 to Thr) in Senecio vulgaris L. confers resistance to several PS II-inhibiting herbicides.
PubMed:
Diffuse geographic distribution of herbicides in northern prairie wetlands.
PubMed:
Mode of action of photosynthesis inhibiting 4-hydroxy-benzonitriles containing nitro group.
PubMed:
Carboxylesterase activities toward pesticide esters in crops and weeds.
PubMed:
A psbA mutation in Kochia scoparia (L) Schrad from railroad rights-of-way with resistance to diuron, tebuthiuron and metribuzin.
PubMed:
Comparative sensitivity of Selenastrum capricornutum and Lemna minor to sixteen herbicides.
PubMed:
Herbicide levels in rivers draining two prairie agricultural watersheds (1984).
PubMed:
Reactive oxygen species in programmed death of pea guard cells.
PubMed:
Chemical weed management in wheat at higher altitudes.
PubMed:
[Determination of six pesticides in milk using cloud point extraction-high performance liquid chromatography].
PubMed:
Pesticides in surface drinking-water supplies of the northern Great Plains.
PubMed:
Autism: transient in utero hypothyroxinemia related to maternal flavonoid ingestion during pregnancy and to other environmental antithyroid agents.
PubMed:
Virtual imprinting as a tool to design efficient MIPs for photosynthesis-inhibiting herbicides.
PubMed:
A multiresidue method using ion-trap gas chromatography-tandem mass spectrometry with or without derivatisation with pentafluorobenzylbromide for the analysis of pesticides in the atmosphere.
PubMed:
Toxicity of a complex mixture of atmospherically transported pesticides to Ceriodaphnia dubia.
PubMed:
Comparative efficacy of five herbicides on winter cereal weeds in semi-arid region of Algeria.
PubMed:
Discrimination and taxonomy of geographically diverse strains of nitrile-metabolizing actinomycetes using chemometric and molecular sequencing techniques.
PubMed:
Microwave assisted solvent extraction and coupled-column reversed-phase liquid chromatography with UV detection use of an analytical restricted-access-medium column for the efficient multi-residue analysis of acidic pesticides in soils.
PubMed:
Herbicide and nutrient transport from an irrigation district into the South Saskatchewan River.
PubMed:
Suspected herbicide toxicosis in a dog.
PubMed:
Nitrilase from Rhodococcus rhodochrous J1. Sequencing and overexpression of the gene and identification of an essential cysteine residue.
PubMed:
Cloning and expression of an Arabidopsis nitrilase which can convert indole-3-acetonitrile to the plant hormone, indole-3-acetic acid.
PubMed:
Responses of marine unicellular algae to brominated organic compounds in six growth media.
PubMed:
Effects of low concentrations of herbicides on full-season, field-grown potatoes.
PubMed:
Radiative and non-radiative charge recombination pathways in Photosystem II studied by thermoluminescence and chlorophyll fluorescence in the cyanobacterium Synechocystis 6803.
PubMed:
Quality control of photosystem II. Cleavage of reaction center D1 protein in spinach thylakoids by FtsH protease under moderate heat stress.
PubMed:
Spatial and geographical variations of urban, suburban and rural atmospheric concentrations of phenols and nitrophenols.
PubMed:
Taking stock of herbicide-resistant crops ten years after introduction.
PubMed:
Acceptor and donor-side interactions of phenolic inhibitors in Photosystem II.
PubMed:
Singlet oxygen production in herbicide-treated photosystem II.
PubMed:
Study of matrix effects on the direct trace analysis of acidic pesticides in water using various liquid chromatographic modes coupled to tandem mass spectrometric detection.
PubMed:
Analysis of acidic pesticides using in situ derivatization with alkylchloroformate and solid-phase microextraction (SPME) for GC-MS.
PubMed:
Modelling agrochemical dissipation in surface microlayers following aerial deposition
PubMed:
Primary structure of an aliphatic nitrile-degrading enzyme, aliphatic nitrilase, from Rhodococcus rhodochrous K22 and expression of its gene and identification of its active site residue.
PubMed:
Synthesis of aryl D-gluco- and D-galacto-pyranosides and 1-O-acyl-D-gluco- and -D-galacto-pyranoses exploiting the Mitsunobu reaction. Influence of the pKa of the acid on the stereoselectivity of the reaction.
PubMed:
Evaluation of polyurethane foam as a trapping medium for herbicide vapor in air monitoring and worker inhalation studies.