| Revision as of 09:29, 15 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: KEGG.← Previous edit |
Latest revision as of 23:40, 17 November 2024 edit undoRustyOldShip (talk | contribs)Extended confirmed users502 edits 1974 USA usage quantity |
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{{chembox |
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| verifiedrevid = 396303272 |
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| verifiedrevid = 443428550 |
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|ImageFile=Bromoxynil.png |
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| ImageFile = Bromoxynil.png |
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|ImageSize=200px |
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| ImageSize = 160 |
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| ImageAlt = Skeletal formula of bromoxynil |
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|IUPACName=3,5-dibromo-4-hydroxybenzonitrile |
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| ImageFile1 = Bromoxynil-3D-spacefill.png |
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|OtherNames= |
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| ImageSize1 = 170 |
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| ImageAlt1 = Space-filling model of the bromoxynil molecule |
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| PIN = 3,5-Dibromo-4-hydroxybenzonitrile |
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| OtherNames = Brominal, Bromotril, Bronate, Buctril, Certrol B, Litarol, M&B 10064, Merit, Pardner, Sabre, Torch |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 14775 |
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| ChemSpiderID = 14775 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C04178 |
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| KEGG = C04178 |
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| InChI = 1/C7H3Br2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H |
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| InChI = 1/C7H3Br2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H |
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| StdInChIKey = UPMXNNIRAGDFEH-UHFFFAOYSA-N |
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| StdInChIKey = UPMXNNIRAGDFEH-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=1689-84-5 |
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| CASNo = 1689-84-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=15531 |
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| UNII = J46EK95K0P |
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| PubChem = 15531 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 453905 |
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| ChEMBL = 453905 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = Brc1cc(C#N)cc(Br)c1O |
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| ChEBI = 17192 |
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| SMILES = Brc1cc(C#N)cc(Br)c1O |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=7 | H=3 | Br=2 | N=1 | O=1 |
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| Formula=C<sub>7</sub>H<sub>3</sub>Br<sub>2</sub>NO |
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| Appearance= colorless or white solid |
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| MolarMass=276.91 g/mol |
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| Density=2.243 g/mL |
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| MeltingPt=194–195 °C |
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| Solubility= organic solvents |
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|Section3={{Chembox Hazards |
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'''Bromoxynil''' is an ] with the formula HOBr<sub>2</sub>C<sub>6</sub>H<sub>2</sub>CN. It is classified as a ] ], and as such sold under many trade names. It is a white solid. It works by inhibiting ]. It is moderately toxic to mammals. |
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'''Bromoxynil''' is a ] ], which is distributed as a ] in ] II (moderately toxic), and not available for homeowner use. Trade names include Brominal, Bromotril, Bronate, Buctril, Certrol B, Litarol, M&B 10064, Merit, Pardner, Sabre, and Torch. It is used for post-emergent control of ] ]s. It is especially effective in the control of weeds in ], ], ], ]s, ], ], ], and on non-cropland. It works by inhibiting ]. Lethal doses in mammals range between 60 and 600 ] ingested per ] of body weight, and ] 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.<ref>{{cite web|url=http://ace.orst.edu/info//extoxnet/pips/bromoxyn.htm|title=Extension Toxicology Network: Pesticide information profiles}}</ref> |
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It is used in Australia,<ref>{{cite web |title=4Farmers Bromoxynil 200 |url=https://4farmers.com.au/products/herbicides/bromoxynil-200/ |website=4farmers.com.au |publisher=4Farmers Australia}}</ref> New Zealand,<ref>{{cite web |title=APP203468-Final-Decision-Signed.pdf |url=https://www.epa.govt.nz/assets/FileAPI/hsno-ar/APP203468/ae23a99d07/APP203468-Final-Decision-Signed.pdf |website=www.epa.govt.nz}}</ref> and the USA, which used 614,000 lbs of it in 1974.<ref>{{cite web |last1=US EPA |first1=OCSPP |title=EPA Implements Protections for Endangered Fish Species from Four Pesticides |url=https://www.epa.gov/pesticides/epa-implements-protections-endangered-fish-species-four-pesticides |website=www.epa.gov |language=en |date=1 February 2023}}</ref><ref>{{cite web |title=Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974 |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=91012P4O.txt |website=epa.gov |publisher=EPA |date=1977}}</ref> |
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In the Great Plains region of Canada it is widely used on cereal grains. Average levels detected in drinking water were 1 ] per ], but 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.<ref>{{cite journal|url=http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=17687445|title=Pesticides in Surface Drinking-Water Supplies of the Northern Great Plains|author=David B. Donald, Allan J. Cessna, Ed Sverko, and Nancy E. Glozier|journal=Environ Health Perspect. |year=2007|volume=115|issue=8|pages=1183–1191|pmid=17687445|doi=10.1289/ehp.9435|pmc=1940079}}</ref> |
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==Production and use== |
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Bromoxynil decomposes readily in soil, with a half life of approximately two weeks. Persistence increases in soils with elevated clay or organic matter content, suggesting the compound has somewhat limited ] 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 ] by the microorganism, Desulfitobacterium chlororespirans.<ref>Cupples, A. M., R. A. Sanford, and G. K. Sims. 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.</ref> |
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It is produced by bromination of 4-hydroxybenzonitrile. |
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It is a post-emergence to control annual broadleaved weeds.<ref name= Ullmanns>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}}</ref> |
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==Degradation== |
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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 ] 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 ] by the microorganism '']''.<ref>{{cite journal | vauthors=Cupples AM, Sanford RA, Sims GK | year = 2005 | title = Dehalogenation of Bromoxynil (3,5-Dibromo-4-Hydroxybenzonitrile) and Ioxynil (3,5-Diiodino-4-Hydroxybenzonitrile) by Desulfitobacterium chlororespirans | journal = Applied and Environmental Microbiology | volume = 71 | issue = 7 | pages = 3741–3746 | doi = 10.1128/AEM.71.7.3741-3746.2005 | pmid = 16000784 | pmc = 1169022}}</ref> |
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In the Great Plains region of Canada, where it is widely used on cereal grains, average levels detected in drinking water were 1 ] 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.<ref>{{cite journal|title=Pesticides in Surface Drinking-Water Supplies of the Northern Great Plains|vauthors=Donald DB, Cessna AJ, Sverko E, Glozier NE |journal=Environ. Health Perspect. |year=2007 |volume=115 |issue=8 |pages=1183–1191 |pmid=17687445 |doi=10.1289/ehp.9435 |pmc=1940079}}</ref> |
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==Safety== |
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Lethal doses in mammals range between 60 and 600 ] ingested per kilogram, and ] 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.<ref>{{cite web |url=http://ace.orst.edu/info//extoxnet/pips/bromoxyn.htm |title=Extension Toxicology Network: Pesticide information profiles |url-status=dead |archiveurl=https://web.archive.org/web/20070401230247/http://ace.orst.edu/info/ |archivedate=2007-04-01 }}</ref> |
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In the ] it is distributed as a ] in ] II (moderately toxic) and not available for homeowner use. |
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Bromoxynil's taste is "slight, not characteristic".<ref>{{cite journal |title=Technical Bulletin Ioxynil and Bromoxynil Selective Herbicides |journal=International Journal of Pest Management: Part C |date=September 1968 |volume=14 |issue=3 |pages=301–322 |doi=10.1080/05331856809438464 |url=https://www.tandfonline.com/doi/epdf/10.1080/05331856809438464?needAccess=true}}</ref> |
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== Tradenames == |
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Bromoxynil has been sold as: Brominal, Nu-Lawn Weeder, (]), Buctril, and Chipco Buctril, (]).<ref>{{cite book |last1=Elmore |first1=C. L. |last2=McHenry |first2=W. B. |last3=Smith |first3=N. L. |last4=Shaefer |first4=K. M. |title=COMMON AND PROPRIETARY TRADE NAMES OF HERBICIDES: A Cross Indexed Guide |date=April 1980 |publisher=Division of Agricultural Sciences University of California}}</ref> This list is incomplete. |
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==References== |
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==References== |
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==External links== |
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*{{PPDB|96}} |
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{{Herbicides}} |
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{{Herbicides}} |
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