Chlorbromuron
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Chlorbromuron
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CAS No:
13360-45-7
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Formula:
C9H10BrClN2O2
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Chemical Name:
Chlorbromuron
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Synonyms:
Urea,N′-(4-bromo-3-chlorophenyl)-N-methoxy-N-methyl-;Urea,3-(4-bromo-3-chlorophenyl)-1-methoxy-1-methyl-;N′-(4-Bromo-3-chlorophenyl)-N-methoxy-N-methylurea;C 6313;Maloran;Chlorbromuron;N-(4-Bromo-3-chlorophenyl)-N′-methoxy-N′-methylurea;3-(4-Bromo-3-chlorophenyl)-1-methoxy-1-methylurea;1-(3-Chloro-4-bromophenyl)-3-methyl-3-methoxyurea;N-(4-Bromo-3-chlorophenyl)-N′-methyl-N′-methoxyurea;3-(3-Chloro-4-bromophenyl)-1-methyl-1-methoxyurea;3-(3-Chloro-4-bromophenyl)-1-methoxy-1-methylurea;N-(3-Chloro-4-bromophenyl)-N′-methoxy-N′-methyl-urea;Bromex (herbicide);Bromex;N-(3-Chloro-4-bromophenyl)-N′-methoxy-N′-methylurea;1-(4-Bromo-3-chlorophenyl)-3-methoxy-3-methylurea
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CAS No:
Chlorbromuron Basic Attributes
293.54
293.54
236-411-9
2X2DQC5EHG
DTXSID6040290
WHITE CRYSTALLINE|Off white color, crystalline|Colorless powder
29280000
Characteristics
41.6
3.09
1.68 g/cm3 @ Temp: 20 °C
95-97 °C
1.6160 (estimate)
In water 35 mg/l (20 deg C). In acetone 460, dichloromethane 170, hexane 89, benzene 72, isopropanol 12 (all in g/kg, 20 deg C).
3.97X10-7 mm Hg @ 20 deg C
Oral-rat LD50: 2150 mg/kg
Thermal decomposition emits toxic nitrogen oxides, chlorides, bromide fumes
MILD ODOR
152.25 Ų [M+H]+ [CCS Type: TW]
Slowly hydrolyzed in neutral, slightly acidic, and slightly alkaline media.
NONCORROSIVE
Safety Information
NONH for all modes of transport
2
36/38-36
26
YS2800000
Xi
The warehouse is low-temperature, ventilated and dry
SUBSTITUTED UREAS ARE CHARACTERISTICALLY HIGHLY STABLE /SUBSTITUTED UREA HERBICIDES/
P305 + P351 + P338
H315-H319-H332
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.
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
WASH HANDS WITH SOAP AND WATER BEFORE EATING, DRINKING OR SMOKING. DO NOT CONTAMINATE FOOD OR FEED. AVOID REPEATED OR PROLONGED CONTACT WITH SKIN. WEAR CLEAN CLOTHING. WASH CLOTHES BEFORE REUSING. DO NOT CONTAMINATE WATER BY DUMPING TANK WASHINGS IN PONDS OR STREAMS. DESTROY EMPTY CONTAINERS BY BURNING. DO NOT INHALE SMOKE FROM BURNING CONTAINERS.
Skin and eye irritant.
Toxicity
moderately toxic
LD50 Rabbit dermal >10,000 mg/kg
Chlorbromuron's former use(1) as a selective herbicide(2) resulted in its direct release to the environment(SRC).
Terrestrial Fate: At application rates of 0.75 to 1 kg additive ingredient/ha, it can persist in soil for eight days or ... longer.|STABLE IN WATER OVER WIDE RANGE OF PH VALUES.|Duration of /herbicidal/ activity in soil greater than 56 days.|... FIELD & LAB SOIL DISSIPATION STUDIES SHOW CHEM HALF-LIFE FOR CHLORBROMURON OF APPROX 45 DAYS.|For more Environmental Fate (Complete) data for CHLORBROMURON (7 total), please visit the HSDB record page.
PHOTODECOMPOSITION UNDER FIELD CONDITIONS IS NOT EXPECTED TO CONTRIBUTE SIGNIFICANTLY TO DISSIPATION OF CHLORBROMURON.|The rate constant for the vapor-phase reaction of chlorbromuron with photochemically produced hydroxyl radicals has been estimated as 1.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 1.5 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC).
Bioconcentration factor predicted from water solubility = 68 (calculated); predicted from soil adsorption coefficient = 25 (calculated). /From table/|An estimated BCF value of 130 was calculated for chlorbromuron(SRC), using a measured log Kow of 3.09(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is high(SRC).
501.19 L/kg|... FIELD STUDIES DEMONSTRATE RUNOFF UNDER NORMAL USE CONDITIONS IS INSIGNIFICANT. ... /IT/ IS LEACHED TO MODERATE EXTENT IN SOIL WHICH IS IMPORTANT FOR OBTAINING CONTROL OF DEEP GERMINATING WEEDS.|Soil adsorption coefficient: 460 (Experimental); 510 (Calculated). /From table/|An Rf value of 0.14 was measured for chlorbromuron on Hagerstown soil TLC plates(1). An average Koc of 380 was measured for 17 Australian soils(2). An average Koc of 217 was reported for chlorbromuron(3). Koc values from 561 to 3262 were measured in 5 Czechoslovakian soils with a mean value of 1557; adsorption was thought to be related to soil organic matter content(4). According to a recommended classification scheme(5), these measured Koc values suggest that chlorbromuron has slight to moderate mobility in soil(SRC). The vertical distribution of chlorbromuron in a sandy soil (pH=5.9, organic matter=1.13%) was measured following 10 cm of rain; concns were >2, 0, 0, 0 mg/kg at depths of 0-2.5, 2.5-5, 5-7.5, and 7.5-10 cm, respectively(2).
VOLATILIZATION IS NOT EXPECTED TO CONTRIBUTE TO DISSIPATION OF CMPD IN FIELD.|The Henry's Law constant for chlorbromuron is estimated as 4.4X10-9 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 3.97X10-7 mm Hg(1), and water solubility, 35 mg/l(2). This value indicates that chlorbromuron will be essentially nonvolatile from water surfaces(3,SRC). Chlorbromuron's values for vapor pressure(1) and Henry's Law constant(1,2,SRC) indicate that volatilization from dry and moist soil surfaces should not occur(SRC).
The bulb of rape celery grown in the presence of chlorbromuron did not contain measurable concns of this herbicide (detection limit=0.02 ug/g fresh weight)(1). Chlorbromuron was detected in 12 of 26 composite carrot samples collected from farm deliveries in Ontario, Canada between 1980 and 1985 (concns from 0.03-0.14 mg/kg)(2).
The general population may be exposed to chlorbromuron through the ingestion of contaminated food. Occupational exposure may be through inhalation or dermal contact. (SRC)
Drug Information
WHEN ... ADMIN ORALLY TO RATS /(14)C-LABELED/, IT WAS OBSERVED THAT TOTAL RADIOACTIVITY WAS RAPIDLY & EFFICIENTLY ELIM IN URINE & FECES. ... 90% OR MORE OF RADIOACTIVITY APPLIED WAS ACCOUNTED FOR IN EXCRETA WITHIN 72 HR AFTER ADMIN.|Dermal absorption is not significant.
WHEN ... (14)C-CHLORBROMURON ... /WAS/ ADMIN TO RATS, NO MORE THAN 0.1-2% OF RADIOACTIVITY APPLIED WAS ACCOUNTED FOR BY CO2 IN EXPIRED AIR ... NEITHER THE UNCHANGED HERBICIDES NOR THEIR METABOLITES HAVE BEEN DECARBOXYLATED TO ANY MAJOR EXTENT IN THESE ANIMALS. ... NO SIGNIFICANT METABOLITES OF ANILINE ... /OBSERVED IN/ EXCRETA OR TISSUES ...|THE RATE OF ABSORPTION, TRANSLOCATION, & SUBSEQUENT METABOLISM OF CHLORBROMURON DIFFERS WITH PLANT SPECIES THUS AFFECTING THE END METABOLITES OBSERVED.|CHLORBROMURON HAS BEEN SHOWN TO UNDERGO 3-STEP DEGRADATION PROCESS IN PLANTS. FIRST 2 STEPS ARE DEMETHYLATION TO A MONOMETHYL THEN TO A DEMETHYL INTERMEDIATE. THIRD STEP IS DEAMINATIVE-DECARBOXYLATION THAT PRODUCES ANILINE MOLECULE.|Ring hydroxylation of /chlorbromuron/ in animal tissues /has been/ described.
THE PHYTOTOXIC SYMPTOMS ASSOCIATED WITH CHLORBROMURON ARE APPARENT IN THE LEAVES. THIS RESPONSE VARIES FROM A CONDITION OF RAPID INITIAL CHLOROSIS FOLLOWED BY NECROSIS FOR HIGH CONCN TO AN EARLY CHLOROSIS WITH SUBSEQUENT RECOVERY FOR SUBLETHAL CONCN. THE PRIMARY EFFECT OF CHLORBROMURON IS INHIBITION OF HILL REACTION. THIS INVOLVES OXYGEN EVOLUTION SITE IN PHYTOSYSTEM II. ... PREVENTS FORMATION OF ATP, & NADPH ... NECESSARY FOR CO2 FIXATION.
Treatment should include decontamination and aggressive supportive care. Additionally, methylene blue, 1 to 2 mg/kg/dose, should be given if significant methemoglobinemia is present. /Urea-substituted herbicides/
chlorbromuron
Chlorbromuron Use and Manufacturing
BROMINATION OF N-(3-CHLOROPHENYL)-N'-METHOXY-N'-METHYL UREA.|m-Chloroaniline + phosgene + N,O-dimethyl-hydroxylamine + bromine (phosgenation/isocyanate addition/ring bromination)
Discontinued
MALORAN 50 WP- 50% ACTIVE MATERIAL. GRANULES OF VARIOUS CONCN. "C 260 50 WP"- MIXT OF CHLORBROMURON & BROMOFENOXIM IN RATIO OF 1:2.|Wettable powder 50%.|Technical material contains 95% active ingredient.|Bromex (herbicide)|(chlorbromuron +) terbuthylazine; amitrole + simazine
Maloran 50WP /WP = wettable powder/ with Lasso 4EC (tank mix) for use on soybeans. Maloran and Igran in winter wheat (Idaho, Oregon, and Washington state only).|Phenylureas can be easily halogenated in the p-position. Advantage is taken of such a procedure to synthesize the brominated phenylurea ... chlorbromuron.|DEVELOPED BY CIBA-GEIGY LTD & INTRODUCED IN 1961. DESCRIBED BY GREEN, DH ET AL, PROC 8TH BRIT WEED CONTROL CONF, 363, 1966. BRITISH PATENT 965,313. ... HERBICIDE FOR PRE-EMERGENCE CONTROL OF BROAD LEAF & GRASSY WEEDS IN CARROTS, SOYBEANS, SUNFLOWERS, PEAS & POTATOES @ 1.0-2.5 KG ACTIVE INGREDIENT/HECTARE; FOR POST-EMERGENCE USE ON CARROTS & TRANSPLANTED CELERY @ 0.75-1.5 KG ACTIVE INGREDIENT/HECTARE.
DETERMINATION IN TECHNICAL & FORMULATED PRODUCTS BY USE OF LIQ CHROMATOGRAPHY.|SUBSTITUTED UREAS & RELATED HERBICIDE RESIDUES WERE DETERMINED IN SOILS BY ACETONE EXTRACTION, ALKALINE HYDROLYSIS, STEAM DISTILLATION, & CONCN OF ANILINES IN TOLUENE. ANILINES DETERMINED BY GC WITH ELECTRON-CAPTURE DETECTOR.|DIRECT DETERMINATION BY HIGH-PERFORMANCE REVERSED-PHASE LIQ CHROMATOGRAPHY IS DESCRIBED. IT IS SUITABLE FOR DETERMINING UREA HERBICIDE RESIDUES IN SOIL & FOOD PRODUCTS.|Residues may be analyzed following hydrolysis to bromo-chloraniline which is diazotized and coupled with N-(1-naphthyl) ethylenediamine, and determined colorimetrically.|For more Analytic Laboratory Methods (Complete) data for CHLORBROMURON (14 total), please visit the HSDB record page.
Agrochemicals -> Herbicides|HERBICIDES
Computed Properties
Molecular Weight:293.54
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:291.96142
Monoisotopic Mass:291.96142
Topological Polar Surface Area:41.6
Heavy Atom Count:15
Complexity:230
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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