{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443816837 | ImageFile=Bromacil skeletal.svg | IUPACName=5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1''H'',3''H'')-dione or 5-bromo-3-sec-butyl-6-methyluracil | OtherNames=Bromazil, Borea, Bromax 4G, Cynogan, Uragan, 5-Bromo-6-methyl-3-(1-methylpropyl)uracil |Section1={{Chembox Identifiers | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C10911 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 3177 | InChI = 1/C9H13BrN2O2/c1-4-5(2)12-8(13)7(10)6(3)11-9(12)14/h5H,4H2,1-3H3,(H,11,14) | InChIKey = CTSLUCNDVMMDHG-UHFFFAOYAA | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C9H13BrN2O2/c1-4-5(2)12-8(13)7(10)6(3)11-9(12)14/h5H,4H2,1-3H3,(H,11,14) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = CTSLUCNDVMMDHG-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=314-40-9 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 9040 | PubChem = 9411 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = I048FFR2J0 | EC_number = 206-245-1 | RTECS = YQ9100000 | SMILES=O=C1C(\Br)=C(/NC(=O)N1C(CC)C)C | MeSHName= }} |Section2={{Chembox Properties | Formula=C<sub>9</sub>H<sub>13</sub>BrN<sub>2</sub>O<sub>2</sub> | MolarMass =261.1157 | Appearance=Odorless, colorless to white, crystalline solid | Density= 1.46 g/cm<sup>3</sup> | MeltingPtC = 157.5 to 160 | MeltingPt_notes = sublimes<ref name=PGCH/> | BoilingPt = none - sublimes<ref name=PGCH/> | Solubility = 0.08% (25°C)<ref name=PGCH/> }} |Section3={{Chembox Hazards | FlashPt= | PEL = none<ref name=PGCH>{{PGCH|0063}}</ref> | REL = TWA 1 ppm (10 mg/m<sup>3</sup>)<ref name=PGCH/> | IDLH = N.D.<ref name=PGCH/> | GHSPictograms = {{GHS07}}{{GHS09}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|302|315|319|335|410}} | PPhrases = {{P-phrases|261|264|270|271|273|280|301+312|302+352|304+340|305+351+338|312|321|330|332+313|337+313|362|391|403+233|405|501}} }} }}
'''Bromacil''' is an organic compound with the chemical formula C<sub>9</sub>H<sub>13</sub>BrN<sub>2</sub>O<sub>2</sub>, commercially available as a herbicide. Bromacil was first registered as a pesticide in the U.S. in 1961,<ref name="EPA">United States Environmental Protection Agency. "Bromacil". 1996, p.1-11. Accessed October 9, 2012</ref> and by 1974 {{convert|1017000|lbs|kg}} was used annually in the US, largely by government and industry.<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> It is used for brush control on non-cropland areas.<ref name="Cornell">Cornell University. “Bromacil”. 1993, p. 1. Accessed October 9, 2012</ref> It works by interfering with photosynthesis by entering the plant through the root zone and moving throughout the plant.<ref name="Power">USDOE-Bonneville Power Administration. 2000, p.1-9. Accessed October 9, 2012</ref> Bromacil is one of a group of compounds called substituted uracils. These materials are broad spectrum herbicides used for nonselective weed and brush control on non-croplands, as well as for selective weed control on a limited number of crops, such as citrus fruit and pineapple.<ref name="Cornell" /> Bromacil is also found to be excellent at controlling perennial grasses.
Bromacil's HRAC classification is Group C1, Group C (global, Aus), Group 5 (numeric), as it inhibits photosynthesis at photosystem II.<ref>{{cite web |title=Classification of Herbicides According to Site of Action |url=https://www.weedscience.org/Documents/ShowDocuments.aspx?DocumentID=1193 |access-date=19 July 2025}}</ref>
==Safety== There are quite a few safety precautions that should be taken when dealing with Bromacil. Dry formulations containing bromacil must bear the word "Caution" and liquid formulas must signal "Warning."<ref name="Cornell" /> Care should be exercised when spraying Bromacil on plants because it will also stop the photosynthesis of the adjacent non-target plants, therefore killing them. Bromacil should never be used in residential or recreation areas for risk of exposure. Bromacil is slightly toxic if individuals accidentally eat or touch residues and practically nontoxic if inhaled. Bromacil is a mild eye irritant and a very slight skin irritant. It is not a skin sensitizer.<ref name="Wash">Washington State Department of Transportation. “Bromacil”. 2006, p.1-4. Accessed October 9, 2012</ref> In studies using laboratory animals, bromacil is slightly toxic by the oral, dermal, and inhalation routes and has been placed in Toxicity Category IV (the lowest of four categories) for these effects.<ref name="EPA" /> This herbicide should be stored in a cool, dry place and after any handling a thorough hand-washing is advised.
In regards to occupational exposure, the National Institute for Occupational Safety and Health has recommended workers handing bromacil not exceed an exposure of 1 ppm (10 mg/m<sup>3</sup>) over an eight-hour time-weighted average.<ref name=pocket>{{cite web | last = Centers for Disease Control and Prevention | first = | author-link = | title = Bromacil | work = NIOSH Pocket Guide to Chemical Hazards | publisher = | date = 4 April 2011 | url = https://www.cdc.gov/niosh/npg/npgd0063.html | doi = | accessdate = 13 November 2013}}</ref>
==Facts== Bromacil (40%) is combined with the active ingredient diuron in the herbicide Krovar, which is used by companies such as the Washington State Department of Transportation (WSDOT). It is in a group of chemicals that are absorbed through the gut and excreted primarily in the urine. The half-life of bromacil in soils is about 60 days, but as long as 8 months in some conditions.<ref name="Wash" /> Bromacil is available in granular, liquid, water-soluble liquid, and wettable powder formulations.<ref name="Cornell" /> Because bromacil is a possible human carcinogen and systemic toxicity may result from intermediate exposure (one week to several months), U.S. Environmental Protection Agency (EPA) assessed risk to workers using several major exposure scenarios. Bromacil is stable to hydrolysis under normal environmental conditions.<ref name="EPA" />
==Applications== Bromacil is applied mainly by sprayers including boom, hand-held, knapsack, compressed air, tank-type, and power sprayers. Bromacil is also applied using aerosol, shaker, or sprinkler cans. Solid forms of bromacil are spread using granule applicators and spreaders. In the United States, application using aircraft is allowed only for Special Local Need registrations to control vegetation on the Department of Defense's Yakima Firing Center in the state of Washington.<ref name="EPA" />
==References== <references/>
Category:Herbicides Category:Uracil derivatives Category:Organobromides Category:Sec-Butyl compounds Category:Group 5 herbicides