1689-84-5

Basic information

• Product Name: Bromoxynil
• Synonyms: 4-HYDROXY-3,5-DIBROMOBENZONITRILE;3,5-DIBROMO-4-HYDROXYBENZONITRILE;3,5-DIBROMO-4-HYDROXYPHENYL CYANIDE;2，6-Dibromo-4-cyanophenol;MB 10064;EMBLEM;KALEIS;BUCTRIL
• CAS NO: 1689-84-5
• Molecular Formula: C₇H₃Br₂NO
• Molecular Weight: 276.91
• EINECS: 216-882-7
• Product Categories: Aromatic Nitriles;Pesticide Intermediate;Alphabetic;B;BI - BZPesticides&Metabolites;Herbicides;Nitriles;A-BAlphabetic;Alpha sort;Pesticides&Metabolites;Agro-Products;Aromatics
• Mol File: 1689-84-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 189-191 °C(lit.)
• Boiling Point: 265.6 °C at 760 mmHg
• Flash Point: 114.4 °C
• Appearance: Buff, Creamy/Solid
• Density: 2.0926 (rough estimate)
• Vapor Pressure: 0.00552mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: 0-6°C
• PKA: 4.06(at 25℃)
• Water Solubility: 0.13 G/L (25 ºC)
• Merck: 13,1426
• BRN: 2364039
• CAS DataBase Reference: Bromoxynil(CAS DataBase Reference)
• NIST Chemistry Reference: Bromoxynil(1689-84-5)
• EPA Substance Registry System: Bromoxynil(1689-84-5)

Safety Data

• Hazard Codes: T+,N
• Statements: 25-26-43-50/53-63
• Safety Statements: 27/28-36/37-45-60-61-63-28A-28-27
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: DI3150000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 1689-84-5(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 1689-84-5 differently. You can refer to the following data:
1. Off-white to salmon crystalline powder
2. Bromoxynil is a colorless to white crystalline solid or tan powder. Odorless (pure).

Uses

Different sources of media describe the Uses of 1689-84-5 differently. You can refer to the following data:
1. Bromoxynil is a nitrile herbicide. Bromoxynil is effective in post-emergent control of broad leaf weeds in cereal, corn, sorghum, onions, flax, mint, turf, and on non-cropland.
2. Selective contact foliage-applied herbicide used to control many broad-leaved weeds in cereals.

Definition

ChEBI: A dibromobenzene that is 2,6-dibromophenol substituted by a cyano group at position 4.

General Description

Colorless solid. Melting point 382-384°F (194-195°C). Sublimes at 275°F (135°C) under pressure of 0.15 mm Hg. Used as a herbicide.

Reactivity Profile

Bromoxynil is a weak acid.

Hazard

Toxic.

Agricultural Uses

Herbicide: A U.S. EPA restricted Use Pesticide (RUP). For post-emergent control of broadleaf weeds. Used on alfalfa, garlic, corn, sorghum, flax, cereals, turf and on pasture and rangelands.

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 
• 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 
• 2973-77-5 3,5-dibromo-4-hydroxybenzaldehyde 
• 2315-84-6 (2,6-dibromo-4-cyanophenyl) acetate 

Downstream Products

• 3861-38-9 2,6-Dibrom-4-cyanophenyl-propanoat 
• 1689-99-2 bromoxynil octanoate 
• 583879-71-4 4-hydroxy-[3,5-3H₂]benzonitrile 
• 583879-73-6 C₃₅H₃₃⁽³⁾H₂NO₄ 
• 583879-75-8 C₃₀H₂₈⁽³⁾H₂N₂O₄ 
• 583879-74-7 C₃₀H₂₅⁽³⁾H₂NO₃ 
• 141990-38-7 2,6-dibromo-4-cyanophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 141990-52-5 2,6-dibromo-4-cyanophenyl 2,3,4,6-tetra-O-chloroacetyl-α-D-galactopyranoside 
• 141990-43-4 2,6-dibromo-cyanophenyl 2,3,4,6-tetra-O-chloroacetyl-β-D-galactopyranoside 
• 141990-51-4 2,6-dibromo-4-cyanophenyl 2,3,4,6-tetra-O-chloroacetyl-α-D-glucopyranoside 
• 141990-42-3 2,6-dibromo-4-cyanophenyl 2,3,4,6-tetra-O-chloroacetyl-β-D-glucopyranoside 
• 135594-37-5 2,6-dibromo-4-cyanophenyl N-(2,6-dibromo-4-cyanophenoxycarbonyl)sulfamate 
• 141990-39-8 2,6-dibromo-4-cyanophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 73748-59-1 C₈H₂Br₂N₂O₄S 

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 articles and documents

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.

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.