Bromoxynil

Bromoxynil Basic information
Product Name:Bromoxynil
Synonyms:4-HYDROXY-3,5-DIBROMOBENZONITRILE;3,5-DIBROMO-4-HYDROXYBENZONITRILE;3,5-DIBROMO-4-HYDROXYPHENYL CYANIDE;3,5-dibromo-4-hydroxy-benzonitril;3,5-dibromo-4-hydroxybenzonitril(acn);4-Cyano-2,6-dibromophenol;Brittox;brominalindustrial
CAS:1689-84-5
MF:C7H3Br2NO
MW:276.91
EINECS:216-882-7
Product Categories:Agro-Products;Aromatics;Pesticide Intermediate;Alphabetic;B;BI - BZPesticides&Metabolites;Aromatic Nitriles;Herbicides;Nitriles;A-BAlphabetic;Alpha sort;Pesticides&Metabolites
Mol File:1689-84-5.mol
Bromoxynil Structure
Bromoxynil Chemical Properties
Melting point 189-191 °C(lit.)
Boiling point 265.6±40.0 °C(Predicted)
density 2.0926 (rough estimate)
refractive index 1.6400 (estimate)
storage temp. 0-6°C
solubility DMSO (Slightly), Methanol (Slightly)
pka4.06(at 25℃)
form Solid
color Buff, Creamy
Water Solubility 0.13 G/L (25 ºC)
Merck 13,1426
BRN 2364039
CAS DataBase Reference1689-84-5(CAS DataBase Reference)
NIST Chemistry ReferenceBenzonitrile, 3,5-dibromo-4-hydroxy-(1689-84-5)
EPA Substance Registry SystemBromoxynil (1689-84-5)
Safety Information
Hazard Codes T+,N
Risk 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 Data1689-84-5(Hazardous Substances Data)
ToxicityLD50 orally in mice: 111 mg/kg (Carpenter, 1964)
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
Bromoxynil Usage And Synthesis
Chemical PropertiesOff-white to salmon crystalline powder
Chemical PropertiesBromoxynil is a colorless to white crystalline solid or tan powder. Odorless (pure).
UsesBromoxynil 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.
UsesSelective contact foliage-applied herbicide used to control many broad-leaved weeds in cereals.
DefinitionChEBI: A dibromobenzene that is 2,6-dibromophenol substituted by a cyano group at position 4.
General DescriptionColorless 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 ProfileBromoxynil is a weak acid.
HazardToxic.
Agricultural UsesHerbicide: 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 nameBRIOTRIL®; 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 ExposureBromoxynil 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 FateBiological. 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 and
Nitrification 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
ShippingUN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required.
IncompatibilitiesA 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 DisposalDo 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.
BROMOXYNIL-POTASSIUM 4-Hydroxybenzoic acid 4-Nitrobenzonitrile BROMOXYNIL GLUCURONIC ACID TRIACETATE METHYL ESTER BROMOXYNIL (RING 13C6) Bromoxynil 2-Hydroxyphenylacetic acid 4,6-Dihydroxypyrimidine 4-Hydroxybenzaldehyde Triclosan BROMOXYNIL-METHYL ETHER 4-Methoxyphenol BROMOXYNIL GLUCURONIC ACID METHYL ESTER 4-Ethyl-5-fluoro-6-hydroxypyrimidine 1,3-Dibromo-5,5-dimethylhydantoin BROMOXYNIL-HEPTANOATE 2-Cyanophenol BROMOXYNIL-SODIUM

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