Bromacil CAS 314-40-9
Introduction：Basic information about Bromacil CAS 314-40-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Bromacil Basic information
| Product Name: | Bromacil |
| Synonyms: | 2,4(1H,3H)-Pyrimidinedione, 5-bromo-6-methyl-3-(1-methylpropyl)-;3h)-pyrimidinedione,5-bromo-6-methyl-3-(1-methylpropyl)-4(1h;3-sek.Butyl-5-brom-6-methyluracil;5-Bromo-3-sec-butyl-6-methyl-2,4(1H,3H)-pyrimidinedione;5-bromo-3-sec-butyl-6-methyl-uraci;5-Bromo-6-methyl-3-(1-methylpropyl)uracil;5-bromo-6-methyl-3(1-methylpropyl)uracil;Borea |
| CAS: | 314-40-9 |
| MF: | C9H13BrN2O2 |
| MW: | 261.12 |
| EINECS: | 206-245-1 |
| Product Categories: | Alphabetic;B;BI - BZPesticides&Metabolites;Herbicides;Uracil structure;Herbicide |
| Mol File: | 314-40-9.mol |
Bromacil Chemical Properties
| Melting point | 157-160°C |
| density | 1.55 |
| vapor pressure | 0Pa at 25℃ |
| refractive index | 1.5410 (estimate) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | DMSO: Soluble,Methanol: Slightly Soluble |
| pka | 8.79±0.40(Predicted) |
| form | Solid |
| color | White, tan |
| Water Solubility | 0.71g/L(25 ºC) |
| Merck | 13,1365 |
| BRN | 6804755 |
| Exposure limits | NIOSH REL: 1 ppm; ACGIH TLV: TWA 1 ppm. |
| Stability: | Stable. Incompatible with strong acids, strong oxidizing agents. |
| Major Application | agriculture environmental |
| InChI | 1S/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-UHFFFAOYSA-N |
| SMILES | CCC(C)N1C(=O)NC(C)=C(Br)C1=O |
| LogP | 1.71 at 23℃ |
| CAS DataBase Reference | 314-40-9(CAS DataBase Reference) |
| NIST Chemistry Reference | Bromacil(314-40-9) |
| EPA Substance Registry System | Bromacil (314-40-9) |
Safety Information
| Hazard Codes | Xn,N |
| Risk Statements | 22-36/37/38-50-36 |
| Safety Statements | 26-61 |
| OEB | B |
| OEL | TWA: 1 ppm (10 mg/m3) |
| RIDADR | UN3077 9/PG 3 |
| WGK Germany | 2 |
| RTECS | YQ9100000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1 |
| Hazardous Substances Data | 314-40-9(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 5200 mg/kg (Sherman, Kaplan) |
| Description | Bromacil (CAS 314-40-9) belongs to a class of herbicidesknown as uracils, first developed by DuPont in 1962. Itsherbicidal activity is due to inhibition of photosynthesis inseveral species of weeds and brush. Since its introduction in1962, farmers in North and South America and Asia have usedbromacil-containing herbicides for crop protection. |
| Chemical Properties | white to beige crystalline solid |
| Chemical Properties | Bromacil is a noncombustible colorless, crystallinesolid, which may be dissolved in a flammable liquid. |
| Uses | Uracil herbicide applied to soil to control a wide variety of annual and perennialgrasses, broad-leaved weeds and general vegetation on uncropped land. It is also used forselective weed control in apple, asparagus, cane fruit, hops and citrus crops. |
| Uses | Bromacil is a nonselective inhibitor of photosynthesis,absorbed mainly through the root and used for generalweed control on uncropped land at 5–15 kg/ha (2–4 kg/haannual maintenance). It is also used for weed control in citrusplantations and for perennial grass control and annual pineappleplantations. |
| Uses | Herbicide. |
| Definition | Substitute approved by EPA for some uses of 2,4,5-T. |
| General Description | Colorless to white odorless crystalline solid. Used as an herbicide. Commercially available as a wettable powder or in liquid formulations. |
| Reactivity Profile | Bromacil is incompatible with the following: Strong acids (decomposes slowly), oxidizers, heat, sparks, open flames . |
| Hazard | Possible carcinogen. Thyroid effects. |
| Flammability and Explosibility | Not classified |
| Agricultural Uses | Bromacil: Bromacil is used primarily for the control of annual andperennial grasses and broadleaf weeds, both nonselectively onnoncrop lands and selectively for weed-control in citrus and pineapplecrops. The top five applications in California for which thisis used are oranges, lemons, grapefruit, and right-of-ways andlandscapes. A limit of 0.1 mg/kg of agricultural products is set inseveral countries[35]. Not approved for use in EU countries. |
| Trade name | BOREA®; BOROCIL EXTRA®; α-BROMACIL80 WP®; BROMAX®; CROPTEX ONYX®;CYNOGEN®; DuPontTM HERBICIDE 976®; EEREX®;FENOCIL®; HERBICIDE 976®; HIBOR; HYDON®;HYVAR®; HYVAR-X®; HYVAR X BROMACIL®;HYVAR X-L®; HYVAR X WEED KILLER®; HYVARX-WS®; ISOCIL®; KROVAR®; NALKIL®; ROUT®;URAGAN®; URAGON®; UROX®; UROX B WATERSOLUBLE CONCENTRATE WEED KILLER®; UROXHX GRANULAR WEED KILLER®; WEED-BROOM®(mixture of DSMA, Bromacil & 2,4-D) |
| Potential Exposure | Used for general weed or brush controlin noncrop areas and primarily for the control of annualand perennial grasses and broadleaf weeds, both nonselectivelyon noncrop lands and selectively for weed-control ina few crops (citrus and pineapple). A limit of 0.1 mg/kg ofagricultural products is set in several countries. Thoseexposed will be those involved in manufacture, formulation,and application. |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit. |
| Carcinogenicity | No evidence of carcinogenicpotential was seen in rats or dogs fed up to 1250 ppmbromacil for 2 years. Bromacil was not oncogenic inrats fed 50, 250, or 2500 ppm for 2 years. A marginalincrease in the incidence of hepatocellular neoplasms wasseen in mice fed 5000 ppm (but not 250 or 1250 ppm) for 18months. |
| Environmental Fate | Soil. Metabolites tentatively identified in soil were 5-bromo-3-(3-hydroxy-1-methyl propyl)-6-methyluracil, 5-bromo-3-sec-butyl-6-hydroxymethyluracil, 5-bromo-3-(2-hydroxy-1-methylpropyl)-6-methyluracil and carbon dioxide. The presence of uracil prod ucts suggests that bromacil was degraded via hydroxylation of the side chain alkyl groups.In the laboratory, 25.3% of 14C-bromacil degraded in soil to carbon dioxide after 9 weeksbut mineralization in the field was not observed. The half-life of bromacil in a silt loamwas 5–6 months (Gardiner et al., 1969). To a neutral sandy loam soil maintained at a soil water holding capacity of 60%, 2.88ppm of 2-14C-bromacil was applied. After 600 days, 22.1% (0.64 ppm) of the appliedamount was converted to 14CO2 (Wolf and Martin, 1974). The evolution of 14CO2 wassign Residual activity in soil is limited to approximately 7 months (Hartley and Kidd, 1987).In California soils, bromacil was persistent for 30 months (Lange et al., 1968; Weber andBest, 1972). The reported half-life in soil is 60 days (Alva and Singh, 1991 The average half-life for bromacil in soil incubated in the laboratory under aerobicconditions was 132 days (Zimdahl et al., 1970). In field soils, the average disappearancehalf-life was 349 days (Gardiner et al., 1969; Leistra et al., 1975). Under aerobic conditions,the mineralization half-lives for bromacil in soil ranged from 151 days to 4.5 years(Gardiner et al., 1969; Wolf and Martin, 1974). Groundwater. According to the U.S. EPA (1986) bromacil has a high potential to leachto groundwater. |
| Metabolic pathway | The microorganism, a Pseudomonas sp. isolated fromsoil by using bromacil as a sole source of carbon andenergy, shows a potential to decontaminate soilsamples fortified with bromacil under laboratoryconditions. The degradation pathways of bromacil bythe Pseudomonas sp. may include 5-bromouracil asan intermediate which leads to 5-bromodihydroxyluracil. Ozonization, UV photolysis,and sensitized sunlight photodegradation of aqueousbromacil solution lead to photodegradation products.The ozonization yields three main products which areidentified as 3-sec-butyl-5-acetyl-5-hydroxyhydantoin,3-sec-butylparabanic acid, and 3-sec-butyl-5,5-dibromo-6-hydroxyuracil. The main products ofphotoirradiation are 3-sec-butyl-6-methyluracil, itsdimeric compound, and 3-sec-butyl-5-acetyl-5-hydroxyhydantoin. |
| storage | Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Color Code—Green: Generalstorage may be used. Prior to working with bromacil youshould be trained on its proper handling and storage. Storein tightly closed containers in a cool, well-ventilated areaaway from strong acids, oxidizers, heat, and open flame. |
| Shipping | UN2811 Toxic solids, organic, n.o.s., HazardClass: 6.1; Labels: 6.1—Poisonous materials, TechnicalName Required. |
| Toxicity evaluation | Bromacil is a nonvolatile, slightly water-soluble compoundwith a low octanol–water partition coefficient (Kow) and a pKaof 9. Although the lithium salt is more soluble in water thanbromacil, its environmental fate is identical, since the extent ofionization of bromacil, that is, the ratio of unionized bromacilto its anionic form, will be controlled by the pH and bufferingcapacity of the terrestrial or aquatic system to which it isapplied. The physicochemical properties are reflected in theenvironmental fate properties. Bromacil is weakly absorbed tosoil and is considered highly mobile. The low Kow indicates thatbromacil will not bioaccumulate. Bromacil is stable in waterover the pH range of 5–9, and photolyzes through both directand indirect mechanisms in surface water with a half-life of 4–7 days at pH 9. In soil under aerobic conditions in the laboratory,bromacil degrades slowly forming several metabolites asa result of microbial activity. In anaerobic environments, bromacilmay degrade very rapidly through a debrominationreaction. In field dissipation studies, bromacil half-lives of124–1155 days were observed. |
| Incompatibilities | Incompatible with strong acids; oxidizers,heat. Decomposes slowly in strong acids. |
| Waste Disposal | Bromacil should be incineratedin a unit operating @ 850° C equipped with gas scrubbingequipment |
Bromacil Preparation Products And Raw materials
| Preparation Products | trans-Cinnamaldehyde |
