1689-84-5

Usage

Uses

Used in Agricultural Industry:
Bromoxynil is used as a selective contact foliage-applied herbicide for the post-emergent control of broadleaf weeds in various crops. It is effective in controlling weeds in cereals, corn, sorghum, onions, flax, mint, turf, and on non-cropland. It is also used on alfalfa, garlic, pasture, and rangelands.
Used in Cereal Industry:
Bromoxynil is used as a herbicide in the cereal industry to control many broad-leaved weeds, ensuring healthier crop growth and higher yields.

Reactivity Profile

Bromoxynil is a weak acid.

Hazard

Toxic.

Trade name

BRIOTRIL?; BRUCIL?; BRITTOX?; BROMINAL?; BROMINEX?; BROMINAL?; BROMINAL ME-4?; BROMINIL?; BROMILIL PLUS?; Bromox 2E; BROMOTRIL?; BROMOXYNIL NITRILE HERBICIDE?; BRONATE?; BROXYNIL?; BUCTRIL? Bromoxynil; BUCTRIL? GEL HERBICIDE (octanoate); BUCTRIL? 4EC GEL (mixture of bromoxynil octanoate + bromoxynil heptanoate); BUCTRIL INDUSTRIAL?; CHIPCO BUCTRIL?; CHIPCO CRAB-KLEEN?; FLAGON?, 400 EC; HOBANE?; LABUCTRIL?; LITAROL?; M&B 10064?; MB 10064?; MB 10731? (octanoate); M&B 10731?; ME4 BROMINAL?; MERIT?; MEXTROL-BIOX?; MOXY 2E?; NCR CE EE DOV7? (octanoate); NU-LAWN WEEDER?; OXYTRIL M?; PARDNER?; SABRE?; TORCH?

Potential Exposure

Bromoxynil is a hydroxybenzonitrile herbicide used for postemergent control of broadleaf weeds; on alfalfa, garlic, corn, sorghum, flax, cereals, turf and on pasture and rangelands. A United States Environmental Protection Agency RUP.

Environmental Fate

Biological. Duke et al. (1991) reported that bromoxynil can be converted to 3,5- dibromo-4-hydroxybenzoic acid by a microbial nitrolase.Soil. In soils, Klebsiella pneumoniae metabolized bromoxynil to 3,5-dibromo-4- hydroxybenzoic acid and ammonia (McBride et al., 1986). In soil, bromoxynil undergoes nitrile and then amide hydrolysis yielding 3,5-dibromo-4-hydroxybenzoic acid andNitrification in soils is inhibited when bromacil is applied at a concentration of <50 ppm (Debona and Audus, 1970). The half-life in soil is approximately 10 days (Hartley and Kidd, 1987).Plant. In plants, the cyano group is hydrolyzed to an amido group which is subsequently oxidized to a carboxylic acid. Hydrolyzes to hydroxybenzoic acid (Hartley and Kidd, 1987). In plants, bromoxynil may hydrolyze to a benzoic acid (Humburg et al., 1989). Bromoxynil-resistant cotton was recently developed by inserting a bxn gene cloned from the soil bacterium Klebsiella ozaenae. This gene, which encodes a specific nitrolase, converted bromoxynil to its primary metabolite 3,5-dibromo-4-hydroxybenzoic acid (Stalker et al., 1988).Chemical/Physical. Emits toxic fumes of nitrogen oxides and bromine when heated to decomposition (Sax and Lewis, 1987). Reacts with bases forming water-soluble salts (Worthing and Hance, 1991). Bromacil is stable to UV light (Hartley and Kidd, 19

Shipping

UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required.

Incompatibilities

A weak acid; keep away from bases and alkalies. React with boranes, alkalies, aliphatic amines, amides, nitric acid, sulfuric acid. Keep away from oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.) and strong acids.

Waste Disposal

Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Incineration with effluent gas scrubbing is recommended. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. If allowed, Incineration with effluent gas scrubbing is recommended. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

InChI:InChI=1/C7H3Br2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H

Upstream product

• 767-00-0 4-cyanophenol 
• 2973-77-5 3,5-dibromo-4-hydroxybenzaldehyde 
• 2315-86-8 3-bromo-4-hydroxybenzonitrile 
• 126747-14-6 4-cyanophenylboronic acid 
• 25952-74-3 3,5-dibromo-4-hydroxy-benzaldehyde-oxime 
• 106-44-5 p-cresol 
• 60-29-7 diethyl ether 
• 10026-13-8 phosphorus pentachloride 
• 2315-84-6 (2,6-dibromo-4-cyanophenyl) acetate 

Downstream Products

• 1689-97-0 3,5-Dibrom-4-(methyl-propyl-acetoxy)benzonitril 
• 3861-38-9 2,6-Dibrom-4-cyanophenyl-propanoat 
• 1689-99-2 bromoxynil octanoate 
• 1689-91-4 3,5-Dibrom-4-trichloracetoxy-benzonitril 
• 73748-59-1 C₈H₂Br₂N₂O₄S 
• 141990-39-8 2,6-dibromo-4-cyanophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 583879-71-4 4-hydroxy-[3,5-3H₂]benzonitrile 
• 3037-56-7 3,5-dibromo-4-hydroxybenzamide 
• 862730-24-3 3-amino-5-bromo-4-hydroxybenzonitrile 
• 1093395-68-6 methyl 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoate 
• 1093395-81-3 C₃₀H₂₈F₃N₅O₂ 
• 1093395-72-2 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide 
• 1093395-96-0 C₂₉H₂₉N₅O₂ 
• 1292821-38-5 C₃₀H₂₈F₃N₅O₂ 

Related news

Development of an ELISA for the detection of Bromoxynil (cas 1689-84-5) in water09/30/2019

For development of an indirect competitive enzyme-linked immunosorbent assay (ELISA) for the nitrile herbicide bromoxynil, the polyclonal antibodies raised against 2,6-dibromo-4-cyano-phenoxyacetic acid (hapten) conjugated to bovine serum albumin (BSA) by the N-hydroxysuccinimide-activated ester...detailed

Development of an immunochromatographic assay for the rapid detection of Bromoxynil (cas 1689-84-5) in water09/28/2019

A rapid immunochromatographic one-step strip test was developed to specifically determine bromoxynil in surface and drinking water by competitive inhibition with the nano colloidal gold-conjugated monoclonal antibody (mAb). Bromoxynil standard samples of 0.01–10 mg L−1 in water were tested by t...detailed

Bromoxynil (cas 1689-84-5) residues and dissipation rates in maize crops and soil☆10/01/2019

A residue analytical method for the determination of bromoxynil in soil and maize was developed using high performance liquid chromatography with diode-array detector (HPLC-DAD) and high performance liquid chromatography tandem mass spectrometry (HPLC–MS/MS). The residual level and dissipation ...detailed

Mechanism of Bromoxynil (cas 1689-84-5) phototransformation: Effect of medium and surfactant09/27/2019

Bromoxynil (BXN, 3,5-dibromo-4-hydroxybenzonitrile) is a herbicide that is classified as a highly hazardous chemical, toxic for the reproduction. The processes and mechanisms regarding the fate of this compound in the environmental compartments subject to solar light are poorly documented. In th...detailed

Degradation, mineralization of Bromoxynil (cas 1689-84-5) pesticide by heterogeneous photocatalytic ozonation09/26/2019

The photocatalysts of Cs doped bare TiO2, 0.50 and 1.0 wt% were prepared by wet-impregnation method and characterized by XRD, SEM-EDX, TEM, BET, ICP, FTIR, and UV-DRS analyses. The degradation of bromoxynil was investigated under visible irradiation with ozone to compare the efficiency of these ...detailed

Unraveling microbial turnover and non-extractable residues of Bromoxynil (cas 1689-84-5) in soil microcosms with 13C-isotope probing☆09/24/2019

Bromoxynil is a widely used nitrile herbicide applied to maize and other cereals in many countries. To date, still little is known about bromoxynil turnover and the structural identity of bromoxynil non-extractable residues (NER) which are reported to occur in high amounts. Therefore, we investi...detailed

Relevant academic research and scientific papers

Synthesis and evaluation of heterocyclic analogues of bromoxynil

One attractive strategy to discover more active and/or crop-selective herbicides is to make structural changes to currently registered compounds. This strategy is especially appealing for those compounds with limited herbicide resistance and whose chemistry is accompanied with transgenic tools to enable herbicide tolerance in crop plants. Bromoxynil is a photosystem II (PSII) inhibitor registered for control of broadleaf weeds in several agronomic and specialty crops. Recently at the University of Tennessee - Knoxville several analogues of bromoxynil were synthesized including a previously synthesized pyridine (2,6-dibromo-5-hydroxypyridine-2-carbonitrile sodium salt), a novel pyrimidine (4,6-dibromo-5-hydroxypyrimidine-2-carbonitrile sodium salt), and a novel pyridine N-oxide (2,6-dibromo-1-oxidopyridin-1-ium-4-carbonitrile). These new analogues of bromoxynil were also evaluated for their herbicidal activity on soybean (Glycine max), cotton (Gossypium hirsutum), redroot pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), large crabgrass (Digitaria sanguinalis), and pitted morningglory (Ipomoea lacunose) when applied at 0.28 kg ha-1. A second study was conducted on a glyphosate-resistant weed (Amaranthus palmeri) with the compounds being applied at 0.56 kg ha -1. Although all compounds were believed to inhibit PSII by binding in the quinone binding pocket of D1, the pyridine and pyridine-N-oxide analogues were clearly more potent than bromoxynil on Amaranthus retroflexus. However, application of the pyrimidine herbicide resulted in the least injury to all species tested. These variations in efficacy were investigated using molecular docking simulations, which indicate that the pyridine analogue may form a stronger hydrogen bond in the pocket of the D1 protein than the original bromoxynil. A pyridine analogue was able to control the glyphosate-resistant Amaranthus palmeri with >80% efficacy. The pyridine analogues of bromoxynil showed potential to have a different weed control spectrum compared to bromoxynil. A pyridine analogue of bromoxynil synthesized in this research controlled several weed species greater than bromoxynil itself, potentially due to enhanced binding within the PSII binding pocket. Future research should compare this analogue to bromoxynil using optimized formulations at higher application rates.

A scalable and green one-minute synthesis of substituted phenols

A mild, green and highly efficient protocol was developed for the synthesis of substituted phenols via ipso-hydroxylation of arylboronic acids in ethanol. The method utilizes the combination of aqueous hydrogen peroxide as the oxidant and H2O2/HBr as the reagent under unprecedentedly simple and convenient conditions. A wide range of arylboronic acids were smoothly transformed into substituted phenols in very good to excellent yields without chromatographic purification. The reaction is scalable up to at least 5 grams at room temperature with one-minute reaction time and can be combined in a one-pot sequence with bromination and Pd-catalyzed cross-coupling to generate more diverse, highly substituted phenols.

PRODRUGS OF 2-(4-(3-((4-AMINO-7-CYANO-IMIDAZO[2,1-F][1,2,4]TRIAZIN-2-YL)AMINO)PHENYL)PIPERAZ IN-1-YL)PROPANAMIDE DERIVATIVES AS CK2 INHIBITORS FOR THE TREATMENT OF CANCER

PRODRUGS OF IMIDAZOTRIAZINE COMPOUNDS AS CK2 INHIBITORS The invention provides pharmaceutically active compounds of formula (I) and prodrugs thereof. The formula (I) 2-(aminophenylamino)-4- amino-7-cyano-imidazo[2,1-f][1,2,4]triazine derivatives inhibit CK2 protein kinase activity, thereby making them useful for treating cancer, psoriasis and rheumatoid arthritis.

Intermolecular Aryl C?H Amination through Sequential Iron and Copper Catalysis

A mild, efficient and regioselective method for para-amination of activated arenes has been developed through a combination of iron and copper catalysis. A diverse range of products were obtained from an operationally simple one-pot, two-step procedure involving bromination of the aryl substrate with the powerful Lewis acid iron(III) triflimide, followed by a copper(I)-catalysed N-arylation reaction. This two-step dehydrogenative process for the regioselective coupling of aromatic C?H bonds with non-activated amines was applicable to anisole-, phenol-, aniline- and acetanilide-type aryl compounds. Importantly, the arene substrates were used as the limiting reagent and required no protecting-group manipulations during the transformation.

Synthesis and evaluation of heterocyclic analogues of bromoxynil

One attractive strategy to discover more active and/or crop-selective herbicides is to make structural changes to currently registered compounds. This strategy is especially appealing for those compounds with limited herbicide resistance and whose chemistry is accompanied with transgenic tools to enable herbicide tolerance in crop plants. Bromoxynil is a photosystem II (PSII) inhibitor registered for control of broadleaf weeds in several agronomic and specialty crops. Recently at the University of Tennessee-Knoxville several analogues of bromoxynil were synthesized including a previously synthesized pyridine (2,6-dibromo-5-hydroxypyridine-2-carbonitrile sodium salt), a novel pyrimidine (4,6-dibromo-5-hydroxypyrimidine-2-carbonitrile sodium salt), and a novel pyridine N-oxide (2,6-dibromo-1-oxidopyridin-1-ium-4-carbonitrile). These new analogues of bromoxynil were also evaluated for their herbicidal activity on soybean (Glycine max), cotton (Gossypium hirsutum), redroot pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), large crabgrass (Digitaria sanguinalis), and pitted morningglory (Ipomoea lacunose) when applied at 0.28 kg ha-1. A second study was conducted on a glyphosate-resistant weed (Amaranthus palmeri) with the compounds being applied at 0.56 kg ha-1. Although all compounds were believed to inhibit PSII by binding in the quinone binding pocket of D1, the pyridine and pyridine-N-oxide analogues were clearly more potent than bromoxynil on Amaranthus retroflexus. However, application of the pyrimidine herbicide resulted in the least injury to all species tested. These variations in efficacy were investigated using molecular docking simulations, which indicate that the pyridine analogue may form a stronger hydrogen bond in the pocket of the D1 protein than the original bromoxynil. A pyridine analogue was able to control the glyphosate-resistant Amaranthus palmeri with >80% efficacy. The pyridine analogues of bromoxynil showed potential to have a different weed control spectrum compared to bromoxynil. A pyridine analogue of bromoxynil synthesized in this research controlled several weed species greater than bromoxynil itself, potentially due to enhanced binding within the PSII binding pocket. Future research should compare this analogue to bromoxynil using optimized formulations at higher application rates.

Cyclic aromatic analogues of the hendrickson reagent; NMR studies and electrophilic properties

Two novel cyclic aromatic analogues of the Hendrickson POP reagent, 1,1,3,3-tetraphenyl-1,3-dihydro-2,1,3-benzoxadiphosphole-1,3-diium bis(trifluoromethanesulfinate) and bis(trifluoromethanesulfonate), have been readily prepared by the treatment of 1,2-bis(diphenylphosphino)benzene or 1,2-bis(diphenylphosphoryl)benzene, respectively, with trifluoromethanesulfonic anhydride in dichloromethane. 31P and 19F NMR studies indicated that while the latter complex is formed as the sole product, the former species was shown to be the predominant component in equilibrium with 1-(diphenylphosphino)-2-[diphenyl(trifluoromethylsulfonyloxy)phosphonio]benzene trifluoromethanesulfinate and 1,2-bis[diphenyl(trifluoromethylsulfonyloxy) phosphonio]benzene bis(trifluoromethanesulfinate). The dehydrating POP systems were exploited in the conversion of aldoximes into nitriles. The dehydration occurred rapidly at room temperature and produced high yields with a variety of alkyl- and arylaldoximes, tolerating a wide range of substrates and functional groups. Georg Thieme Verlag Stuttgart New York.

A PROCESS FOR THE ECO-FRIENDLY PREPARATION OF 3, 5-DIBROMO-4-HYDROXYBENZONITRILE

A highly pure 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil) has been prepared in high yield from 4-hydroxybenzonitrile using eco-friendly brominating reagent comprising of 2:1 mole ratio of bromide to bromate salts in aqueous acidic medium without any catalyst under ambient conditions with no work up procedure. The product 3,5-dibromo-4-hydroxybenzonitrile was obtained in 91-99% yield with melting point 189-191°C and more than 99% purity by gas chromatographic analysis without any purification.

High atom efficient and environment-friendly preparation of herbicides bromoxynil and ioxynil

High atom efficient and environment-friendly preparation of herbicides bromoxynil and ioxynil using bromide/bromate and iodide/iodate couple as halogenating reagent in water at room temperature is described.

NMR Studies and electrophilic properties of triphenylphosphine-trifluoromethanesulfonic anhydride; a remarkable dehydrating reagent system for the conversion of aldoximes into nitriles

NMR Studies on the reaction of triphenylphosphine with various amounts of triflic anhydride at 0 °C is described. The reagent structure resulting from mixing 1.3 equiv of Ph3P with Tf2O (1.0 mmol) has been established as an equilibrium mixture consisting mainly of triphenyl(trifluoromethylsulfonyloxy)phosphonium trifluoromethanesulfinate and the corresponding bis(triphenyl)oxodiphosphonium trifluoromethanesulfinate dimer. The electrophilic properties of the system have been exploited in the development of a mild method for converting aldoximes into nitriles. The dehydration occurs at 0 °C under very mild conditions by initial activation of the oxime oxygen, followed by treatment with a base and subsequent elimination of triphenylphosphine oxide. The substrate scope and functional group tolerance of this useful method are explored.

Regioselective synthesis of phenols and halophenols from arylboronie acids using solid poly(N-vinylpyrrolidone)/hydrogen peroxide and poly(4-vinylpyridine) /hydrogen peroxide complexes

Solid hydrogen peroxide complexes based on poly(N-vinylpyrrolidone) and poly(4-vinylpyridine) were prepared and used as solid hydroxylating reagents. These solid hydrogen peroxide equivalents are found to be much safer, convenient and efficient reagent systems for the ipso-hydroxylation of arylboronie acids to the corresponding phenols in high yields at a faster rate. The versatility of the reagents has been further expanded for the one-pot synthesis of halophenols. Density functional theory calculations were carried out on hydrogen peroxide complexes of N-ethylpyrrolidone and 4-ethylpyridine as models to get a better understanding of structure and behavior of hydrogen peroxide complexes of the polymers poly(N-vinylpyrrolidone) and poly(4-vinylpyridine) compared to aqueous hydrogen peroxide.