Bromoxynil is an organic compound with the formula HOBr2C6H2CN. It is classified as a nitrileherbicide, and as such sold under many trade names. It is a white solid. It works by inhibiting photosynthesis. It is moderately toxic to mammals.
It is produced by bromination of 4-hydroxybenzonitrile.
It is a post-emergence to control annual broadleaved weeds.[1]
Degradationedit
Bromoxynil decomposes with a half life of approximately two weeks in soil. Persistence increases in soils with elevated clay or organic matter content, suggesting the compound has somewhat limited bioavailability to microorganisms in these environments. Under aerobic conditions in soils or pure cultures, products of bromoxynil degradation often retain the original bromine groups. The herbicide, and one of its common degradation products (3,5-dibromo-4-hydroxybenzoic acid) have been shown to undergo metabolic reductive dehalogenation by the microorganism Desulfitobacterium chlororespirans.[2]
In the Great Plains region of Canada, where it is widely used on cereal grains, average levels detected in drinking water were 1 nanogram per liter. In one case as high as 384 nanograms per liter were detected. Levels of bromoxynil were consistently lower than of several other pesticides tested, and it was observed to undergo greater reduction in water treatment than the others.[3]
Safetyedit
Lethal doses in mammals range between 60 and 600 milligrams ingested per kilogram, and teratogenic effects have been observed in rats and rabbits above 30 milligrams per kilogram. Chronic exposure for more than one year in humans caused symptoms of weight loss, fever, vomiting, headache, and urinary problems in one documented case.[4]
^Franz Müller and Arnold P. Applebyki "Weed Control, 2. Individual Herbicides" in Ullmann's Encyclopedia of Industrial Chemistry 2010 doi:10.1002/14356007.o28_o01
^Cupples AM, Sanford RA, Sims GK (2005). "Dehalogenation of Bromoxynil (3,5-Dibromo-4-Hydroxybenzonitrile) and Ioxynil (3,5-Diiodino-4-Hydroxybenzonitrile) by Desulfitobacterium chlororespirans". Applied and Environmental Microbiology. 71 (7): 3741–3746. doi:10.1128/AEM.71.7.3741-3746.2005. PMC1169022. PMID 16000784.
^Donald DB, Cessna AJ, Sverko E, Glozier NE (2007). "Pesticides in Surface Drinking-Water Supplies of the Northern Great Plains". Environ. Health Perspect. 115 (8): 1183–1191. doi:10.1289/ehp.9435. PMC1940079. PMID 17687445.
Bromoxynil in the Pesticide Properties DataBase (PPDB)
April 26, 2024
bromoxynil, organic, compound, with, formula, hobr2c6h2cn, classified, nitrile, herbicide, such, sold, under, many, trade, names, white, solid, works, inhibiting, photosynthesis, moderately, toxic, mammals, names, preferred, iupac, name, dibromo, hydroxybenzon. Bromoxynil is an organic compound with the formula HOBr2C6H2CN It is classified as a nitrile herbicide and as such sold under many trade names It is a white solid It works by inhibiting photosynthesis It is moderately toxic to mammals Bromoxynil Names Preferred IUPAC name 3 5 Dibromo 4 hydroxybenzonitrile Other names Brominal Bromotril Bronate Buctril Certrol B Litarol M amp B 10064 Merit Pardner Sabre Torch Identifiers CAS Number 1689 84 5 Y 3D model JSmol Interactive image ChEBI CHEBI 17192 Y ChEMBL ChEMBL453905 Y ChemSpider 14775 Y ECHA InfoCard 100 015 348 KEGG C04178 Y PubChem CID 15531 UNII J46EK95K0P Y CompTox Dashboard EPA DTXSID3022162 InChI InChI 1S C7H3Br2NO c8 5 1 4 3 10 2 6 9 7 5 11 h1 2 11H YKey UPMXNNIRAGDFEH UHFFFAOYSA N YInChI 1 C7H3Br2NO c8 5 1 4 3 10 2 6 9 7 5 11 h1 2 11HKey UPMXNNIRAGDFEH UHFFFAOYAP SMILES Brc1cc C N cc Br c1O Properties Chemical formula C 7H 3Br 2N O Molar mass 276 915 g mol 1 Appearance colorless or white solid Density 2 243 g mL Melting point 194 195 C Solubility in water organic solvents Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Production and use 2 Degradation 3 Safety 4 References 5 External linksProduction and use editIt is produced by bromination of 4 hydroxybenzonitrile It is a post emergence to control annual broadleaved weeds 1 Degradation editBromoxynil decomposes with a half life of approximately two weeks in soil Persistence increases in soils with elevated clay or organic matter content suggesting the compound has somewhat limited bioavailability to microorganisms in these environments Under aerobic conditions in soils or pure cultures products of bromoxynil degradation often retain the original bromine groups The herbicide and one of its common degradation products 3 5 dibromo 4 hydroxybenzoic acid have been shown to undergo metabolic reductive dehalogenation by the microorganism Desulfitobacterium chlororespirans 2 In the Great Plains region of Canada where it is widely used on cereal grains average levels detected in drinking water were 1 nanogram per liter In one case as high as 384 nanograms per liter were detected Levels of bromoxynil were consistently lower than of several other pesticides tested and it was observed to undergo greater reduction in water treatment than the others 3 Safety editLethal doses in mammals range between 60 and 600 milligrams ingested per kilogram and teratogenic effects have been observed in rats and rabbits above 30 milligrams per kilogram Chronic exposure for more than one year in humans caused symptoms of weight loss fever vomiting headache and urinary problems in one documented case 4 In the United States it is distributed as a restricted use pesticide in toxicity class II moderately toxic and not available for homeowner use References edit Franz Muller and Arnold P Applebyki Weed Control 2 Individual Herbicides in Ullmann s Encyclopedia of Industrial Chemistry 2010 doi 10 1002 14356007 o28 o01 Cupples AM Sanford RA Sims GK 2005 Dehalogenation of Bromoxynil 3 5 Dibromo 4 Hydroxybenzonitrile and Ioxynil 3 5 Diiodino 4 Hydroxybenzonitrile by Desulfitobacterium chlororespirans Applied and Environmental Microbiology 71 7 3741 3746 doi 10 1128 AEM 71 7 3741 3746 2005 PMC 1169022 PMID 16000784 Donald DB Cessna AJ Sverko E Glozier NE 2007 Pesticides in Surface Drinking Water Supplies of the Northern Great Plains Environ Health Perspect 115 8 1183 1191 doi 10 1289 ehp 9435 PMC 1940079 PMID 17687445 Extension Toxicology Network Pesticide information profiles Archived from the original on 2007 04 01 External links editBromoxynil in the Pesticide Properties DataBase PPDB Retrieved from https en wikipedia org w index php title Bromoxynil amp oldid 1219958214, wikipedia, wiki, book, books, library,
