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Your Location：Home>Product Center >> Pesticide API and intermediates >> Bromacil
  • Bromacil
Name:Bromacil
CAS No:314-40-9

PRODUCT DESCRIPTION

【Name】
Bromacil
【Iupac name】
5-bromo-3-butan-2-yl-6-methyl-1H-pyrimidine-2,4-dione
【CAS Registry number】
314-40-9
【Synonyms】
Uracil,5-bromo-3-sec-butyl-6-methyl- (8CI)
3-sec-Butyl-5-bromo-6-methyluracil
5-Bromo-3-sec-butyl-6-methyluracil
5-Bromo-6-methyl-3-(1-methyl-n-propyl)uracil
5-Bromo-6-methyl-3-(1-methylpropyl)uracil
5-Bromo-6-methyl-3-sec-butyluracil
【EINECS(EC#)】
206-245-1
【Molecular Formula】
C9H13BrN2O2 (Products with the same molecular formula)
【Molecular Weight】
261.116
【Inchi】
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
【Canonical SMILES】
CCC(C)N1C(=O)C(=C(NC1=O)C)Br
【MOL File】
314-40-9.mol

Chemical and Physical Properties

【Appearance】
white to beige crystalline solid
【Density】
1.55
【Melting Point】
157-160℃
【Boiling Point】
411
【Refractive Index】
1.541
【Water】
Stability Stable.
【Solubilities】
Stability Stable.
【Color/Form】
White crystalline solid
Colorless crystals
【Stability】
Stable. Incompatible with strong acids, strong oxidizing agents.
【Storage temp】
0-6°C
【Spectral properties】
Intense mass spectral peaks: 205 m/z (100%), 207 m/z (98%), 41 m/z (68%), 68 m/z (26%)
Intense mass spectral peaks: 162 m/z, 188 m/z, 231 m/z, 260 m/z
【Computed Properties】
Molecular Weight:261.11572 [g/mol]
Molecular Formula:C9H13BrN2O2
XLogP3:2.1
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:2
Tautomer Count:4
Exact Mass:260.01604
MonoIsotopic Mass:260.01604
Topological Polar Surface Area:49.4
Heavy Atom Count:14
Formal Charge:0
Complexity:312
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:1
Effective Rotor Count:2
Conformer Sampling RMSD:0.6
CID Conformer Count:6

Safety and Handling

【Hazard Codes】
Xn: Harmful;N: Dangerous for the environment;
【Risk Statements】
R22
【Safety Statements 】
26-61
【Safety】

Moderately toxic by ingestion. An experimental teratogen. Mutation data reported. Questionable carcinogen. An herbicide. When heated to decomposition it emits very toxic fumes of Br? and NOx.
Hazard Codes:? XnHarmful,NDangerous 
Risk Statements:? 22-36/37/38-50-36?
R22:Harmful if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R50:Very toxic to aquatic organisms.?
R36:Irritating to eyes. 
Safety Statements:? 26-61?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
RIDADR:? UN3077 9/PG 3

【Cleanup Methods】
The efficiency of a photo-oxidation procedure for the detoxification of water containing herbicides of the uracil group was tested by bioassay. Treated herbicide soln were checked for their inhibiting effect on germination and photosynthesis in sorghum (Sorghum bicolor). The treated soln and the main photodegradation products of bromacil and terbacil did not inhibit significantly either germination or seedling development at concn of up to 200 and 10 mg/l, respectively. Preliminary tests with indust waste effluents containing added uracil cmpd showed that these cmpd were rendered non-phytotoxic by the photo-oxidation procedure.
【Transport】
UN3077 9/PG 3
【Fire Potential】
Active ingredient and dry formulations are non-flammable; the liquid formulation (HYVAR-XL) is a combustible mixture which should be kept away from heat and open flame.
【Formulations/Preparations】
USEPA/OPP Pesticide Code 012301; Trade Names: Hyvar X; Weed-Broom; Cyanogan; Uragan; Borea; Borocil 1V; Herbicide 976; Hyvar X bromoacil; Hyvar X weed killer; Hyvarex; Krovar II; Nalkil; Urox B.
Granular, liquid, water soluble liquid, and wettable powder
Bromacil + diuron + terbutyrn
Hyvar X Bromacil (wettable powder: 80% ai), Hyvar X-WS Bromacil (water sol powder: 50% ai), and Hyvar X-L Bromacil (liq concn: 3 lb ai/gal)
Used in mixtures with picloram, diuron, dichlobenil, amitrole plus diuron, sodium chlorate plus sodium metaborate, 2,4-D plus dalapon plus diuron, diuron plus hexazinone, amitrole plus dichlorprop plus diuron.
【Reactivities and Incompatibilities】
Strong acids (decomposes slowly), oxidizers, heat, sparks, open flames.
【Other Preventative Measures】
DO NOT GET IN EYES. AVOID CONTACT WITH SKIN & CLOTHING. AVOID BREATHING SPRAY MIST; WASH THOROUGHLY AFTER HANDLING. IN CASE OF CONTACT, FLUSH EYES OR SKIN WITH PLENTY OF WATER; FOR EYES, GET MEDICAL ATTENTION. /WATER-SOL LIQ/
Do not reuse containers.
Keep away from heat and open flame.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
【Protective Equipment and Clothing】
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]
【Octanol/Water Partition Coefficient】
log Kow= 2.11
【Report】

EPA Genetic Toxicology Program.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Bromacil should be incinerated in a unit operating at 850 deg C equipped with off gas scrubbing equipment.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

BROMINATION OF 3-SEC-BUTYL-6-METHYLURACIL
Bromacil is manufactured by the reaction of phosgene and ammonia with sec-butylamine to produce sec-butylurea, which reacts with ethylacetoacetate to produce 3-sec-butyl-6-methyluracil, which is then brominated to produce bromacil.
Production: s-butylamine + sodium cyanate + ethyl acetoacetate + bromine (cyanate addition/condensation/alpha bromination
U.S. Exports

(1972) APPROX 1.0X10+6 G
U.S. Production

(1972) 1.82X10+9 G
(1974) 6.4X10+9 G (EST)
Consumption Patterns

APPROX 77% FOR INDUSTRIAL/COMMERCIAL USE AS AN HERBICIDE; APPROX 13% FOR AGRICULTURAL USE AS AN HERBICIDE; AND APPROX 10% FOR GOVERNMENT AGENCY USE AS AN HERBICIDE (1972)
In 1992, 1,194,805 pounds of bromacil were applied to citrus crops in the US.
【Usage】

Herbicide.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
【Biomedical Effects and Toxicity】
WHEN HERBICIDE CONCN IN FEED OF COWS WAS 5 & 30 PPM, SECRETION OF INTACT CMPD IN MILK REACHED CONCN OF 0.019 & 0.13 PPM, RESPECTIVELY. BROMACIL WAS ABSENT IN URINE & FECES SAMPLES. RAPID UPTAKE VIA THE ROOTS, SLIGHT ABSORPTION VIA THE LEAF CANOPY.
The uptake and translocation of bromacil was investigated after root application to maize (Zea mays) and bean (Phaseolus vulgaris). 90-100% was recovered in quant radioassays. Absorption of bromacil incr to approx 20% of the applied dose in bean plants after 2 days of exposure, and to approx 11% in maize plants after 4 days. After 4 hr of exposure of the roots approx 1/2 of the absorbed bromacil had accum in the shoots, while greater than or equal to 2/3 was translocated to the shoots after 1-4 days. No metabolites of bromacil were detected in the 2 plant species.
Bromacil is absorbed from the GI tract and appears to be excreted primarily in the urine.
LC50 values for 30-day old fathead minnows (Pimephales promelas) exposed to bromacil were 185, 183, 182, and 167 mg/l at 24, 48, 96, and 168 hr, respectively. In early life-stage exposures, it was not possible to determine a no effect concn for bromacil, as growth was reduced at the lowest exposure of 1.0 mg/l. Bromacil did not accumulate significantly in fish tissue. Rainbow trout (Salmo gairdneri) injected with radiolabeled bromacil eliminated over 90% of the radioactivity within 24 hr.
Absorbed mainly through the roots, with slight absorption through the leaves and stems.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
At 18 mo after spraying 22.4 kg bromacil/ha on abandoned field sites overgrown mainly by little bluestem (Andropogon scoparius), poverty grass (Danthonia spicata), timothy (Phleum pratense), quackgrass (Agropyron repens), goldenrod (Solidago) and Kentucky bluegrass (Poa pratensis), the max recovery of detectable bromacil residues occurred in the loamy sand, followed by decr amt in the silt loam, silty clay loam, and light silty clay loam. Org matter content, cation-exchange capacity, total nitrogen and sol salt concn were significantly correlated with residue persistence and incr depth in all 4 soils.
TERRESTRIAL FATE: BROMACIL WAS INCUBATED IN VARIOUS SOILS TO DETERMINE ITS PERSISTENCE. HALF-LIFE IN FLOODED SOIL WAS 155 DAYS; IN FLOODED SOIL PLUS BEAN STRAW, 198 DAYS.
TERRESTRIAL FATE: When sterilant rates are applied, activity usually is noted for more than one season. The half-life of 2-(14)C-labeled bromacil was determined to be approximately 5 to 6 months when 4 lb/A were applied to the surface of Butlertown silt loam.
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 2.3(2) to 289(3), indicate that bromacil is expected to have very high to moderate mobility in soil(SRC). In one adsorption study, it was determined that a rainfall of 20-23 cm could displace over 96% of applied bromacil(8). Volatilization of bromacil from moist soil surfaces is not expected to be an important fate process(6) given a Henry's Law constant of 1.29X10-10 atm-cu m/mole (SRC), estimated from its vapor pressure, 3.07X10-7 mm Hg(4), and water solubility, 815 mg/l(5). Bromacil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. While losses from soil due to photodecomposition or volatilization are minor(3,7), biodegradation, although slow, is a major degradation pathway for bromacil in both aerobic and anaerobic environments. Bromacil was biodegraded in aerobic soil with a half-life of 275 days; the major degradate was carbon dioxide(9). Anaerobic half-lives of 144 to 198 days have been reported in flooded soil(10).
TERRESTRIAL FATE: Bromacil is relatively persistent in soil. The US Dept of Agric's Pesticide Properties Database lists a soil half-life of 60 days for bromacil(1). In a laboratory study using a sandy loam soil and saturated soil conditions, bromacil had an observed half-life of 144-198 days(2). In an apple orchard study where bromacil was applied annually for 6-7 yrs, bromacil had an apparent half-life of approximately 8 months(3). In field plots treated with 4 lb bromacil per acre, bromacil had a half-life of 5 to 6 months(4); identified metabolites included 5-bromo-3-sec-butyl-6-hydroxymethyl uracil, 5-bromo-3-(2-hydroxy-1-methylpropyl)-6-methyluracil, and 5-bromo-3-(3-hydroxy-1-methylpropyl)-6-methyluracil(4). Degradation of 31-65% was observed in six soils after incubation for 6 months under laboratory conditions(5). Laboratory half-lives of 4-5 months were determined for a loam soil at temperatures of 13.2 and 31.2 deg C(6); faster degradation occurred at warmer temperatures(6).
TERRESTRIAL FATE: A single application of bromacil at 2 lb ai/acre dissipated with half-lives of 155 days from the upper 10 cm of a bare ground plot of silty clay loam soil in Delaware, and 124 days from the upper 10 cm of a bare ground plot of loam soil located in California(1). Bromacil was detected in the upper 10 cm of the Delaware and California plots through 538 and 415 days posttreatment, respectively(1). In general, bromacil was not detected below the 40 cm soil depth at both test sites. This may have been due to the amount and timing of rainfall and/or irrigation at these sites(1).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 2.3(2) to 289(3) indicate that bromacil is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 1.29X10-10 atm-cu m/mole(SRC), estimated from its vapor pressure, 3.07X10-7 mm Hg(5), and water solubility, 815 mg/l(6). Bromacil is stable to hydrolysis(6) and is not susceptible to direct photolysis at pH values of 5 and 7(7). However, in alkaline waters, bromacil may be photolyzed based on a study showing a photolysis half-life of 4-7 days at pH 9(7). Biodegradation is expected to be a major fate process for this compound in water. Based on soil studies, bromacil is expected to be slowly biodegraded under both aerobic and anaerobic conditions(7). A single sediment/water study reported a half-life of 36 days under anaerobic conditions, following a lag phase of 28 days(7). According to a classification scheme(8), whole fish BCF values of 2.8 and 26.5, measured in bluegill sunfish(7) and fathead minnow(9), respectively, suggest the potential for bioconcentration in aquatic organisms is low.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromacil, which has a vapor pressure of 3.07X10-7 mm Hg at 25 deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase bromacil is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 20 hours(SRC), calculated from its rate constant of 1.9X10-11 cu cm/molecule-sec at 25 deg C(SRC), determined using a structure estimation method(3). The rate constant for the vapor-phase reaction of bromacil with ozone has been estimated as 0.16X10-17 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 days at an atmospheric concn of 7X10+11 ozone molecules per cu cm(1). Particulate-phase bromacil may be removed from the air by wet and dry deposition(SRC).

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