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| | Bromoxynil Basic information |
| | 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) | | form | Solid | | pka | 4.06(at 25℃) | | color | Buff, Creamy | | Water Solubility | 0.13 G/L (25 ºC) | | Merck | 13,1426 | | BRN | 2364039 | | Henry's Law Constant | 7.4×102 mol/(m3Pa) at 25℃, Mackay et al. (2006) | | Major Application | agriculture
cleaning products
cosmetics
environmental
food and beverages
personal care | | InChI | 1S/C7H3Br2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H | | InChIKey | UPMXNNIRAGDFEH-UHFFFAOYSA-N | | SMILES | Oc1c(Br)cc(cc1Br)C#N | | CAS DataBase Reference | 1689-84-5(CAS DataBase Reference) | | NIST Chemistry Reference | Benzonitrile, 3,5-dibromo-4-hydroxy-(1689-84-5) | | EPA Substance Registry System | Bromoxynil (1689-84-5) |
| 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 | | Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | | Hazard Classifications | Acute Tox. 1 Inhalation
Acute Tox. 3 Oral
Aquatic Acute 1
Aquatic Chronic 1
Repr. 2
Skin Sens. 1 | | Hazardous Substances Data | 1689-84-5(Hazardous Substances Data) | | Toxicity | LD50 orally in mice: 111 mg/kg (Carpenter, 1964) |
| | Bromoxynil Usage And Synthesis |
| Description | A widely used herbicide. It has a high aqueous solubility and is not considered to be volatile. The potential for leaching to groundwater is considered low, and it is not expected to be persistent in soil or water systems. It is highly toxic to mammals, is an endocrine disrupter and may cause negative reproduction or development effects. It is moderately toxic to most aquatic and terrestrial biodiversity. The main exceptions are a low toxicity to algae and honeybees by the contact route (not the oral route). | | Chemical Properties | Off-white to salmon crystalline powder | | Chemical Properties | Bromoxynil is a colorless to white crystalline
solid or tan powder. Odorless (pure). | | Uses | 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. | | Uses | Selective contact foliage-applied herbicide used to control many broad-leaved weeds
in cereals. | | Production Methods | Bromoxynil is produced commercially through a relatively simple chemical process. The synthesis begins with 4-hydroxybenzonitrile. This compound undergoes electrophilic aromatic substitution using bromine which produces bromoxynil. | | 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® | | Mechanism of action | Selective, contact action with some systemic activity. Inhibits photosynthesis (photosystem II). | | 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 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 | | 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. | | Pesticide Type | Herbicide; Metabolite |
| | Bromoxynil Preparation Products And Raw materials |
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