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Your Location：Home>Product Center >> Pesticide API and intermediates >> Metobromuron
  • Metobromuron
Name:Metobromuron
CAS No:3060-89-7

PRODUCT DESCRIPTION

【Name】
Urea,N'-(4-bromophenyl)-N-methoxy-N-methyl-
【Iupac name】
3-(4-bromophenyl)-1-methoxy-1-methylurea
【CAS Registry number】
3060-89-7
【Synonyms】
Urea,3-(p-bromophenyl)-1-methoxy-1-methyl- (7CI,8CI)
1-(p-Bromophenyl)-3-methoxy-3-methylurea
1-Methoxy-1-methyl-3-(4-bromophenyl)urea
1-Methoxy-1-methyl-3-(p-bromophenyl)urea
3-(4-Bromophenyl)-1-methyl-1-methoxyurea
3-(p-Bromophenyl)-1-methoxy-1-methylurea
3-(p-Bromophenyl)-1-methyl-1-methoxyurea
C 3126
Metbromuron
Metobromuron
Monobromuron
N-(4-Bromophenyl)-N'-methoxy-N'-methylurea
N-(4-Bromophenyl)-N'-methyl-N'-methoxyurea
N-(p-Bromophenyl)-N'-methyl-N'-methoxyurea
Patoran
【EINECS(EC#)】
221-301-5
【Molecular Formula】
C9H11 Br N2 O2 (Products with the same molecular formula)
【Molecular Weight】
259.0998
【Inchi】
InChI=1/C9H11BrN2O2/c1-12(14-2)9(13)11-8-5-3-7(10)4-6-8/h3-6H,1-2H3,(H,11,13)
【InChIKey】
WLFDQEVORAMCIM-UHFFFAOYSA-N
【Canonical SMILES】
CN(C(=O)NC1=CC=C(C=C1)Br)OC
【MOL File】
3060-89-7.mol

Chemical and Physical Properties

【Appearance】
White to brown powder
【Density】
1.534 g/cm3
【Melting Point】
95.5-96 ºC
【Boiling Point】
°Cat760mmHg
【Refractive Index】
1.607
【Flash Point】
°C
【Water】
Solubility: In water 330 mg/l (20 ℃). In acetone 500, dichloromethane 550, methanol 240, toluene 100, octanol 70, chloroform 62.5, hexane 2.6 (all in g/l, 20 ℃).
【Solubilities】
Solubility: In water 330 mg/l (20 ℃). In acetone 500, dichloromethane 550, methanol 240, toluene 100, octanol 70, chloroform 62.5, hexane 2.6 (all in g/l, 20 ℃).
【Color/Form】
CRYSTALS FROM CYCLOHEXANE
WHITE CRYSTALS
【Stability】
Very stable in neutral, weakly acidic and weakly alkaline media; hydrolyzed by strong acids and bases; the formulated product is stable up to 50 C for at least 2 yr.
【Storage temp】
APPROX 4°C
【Spectral properties】
Intense mass spectral peaks: 61 m/z (100%), 46 m/z (22%), 258 m/z (14%), 91 m/z (14%)
【Computed Properties】
Molecular Weight:259.09984 [g/mol]
Molecular Formula:C9H11BrN2O2
XLogP3:2.4
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:2
Tautomer Count:2
Exact Mass:258.00039
MonoIsotopic Mass:258.00039
Topological Polar Surface Area:41.6
Heavy Atom Count:14
Formal Charge:0
Complexity:193
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:1
Effective Rotor Count:4
Conformer Sampling RMSD:0.6
CID Conformer Count:22

Safety and Handling

【Hazard Codes】
Xn: Harmful;F: Flammable;
【Risk Statements】
R22
【Safety Statements 】
16-26-36
【Safety】

Moderately toxic by ingestion and intraperitoneal routes. An eye irritant. When heated to decomposition it emits toxic fumes of Br− and NOx.
Safety Information about 3-(4-Bromophenyl)-1-methoxy-1-methylurea (CAS NO.3060-89-7):
Hazard Codes:  
Xn:   F: 
Risk Statements about 3-(4-Bromophenyl)-1-methoxy-1-methylurea (CAS NO.3060-89-7): 
R22: Harmful if swallowed.
R36: Irritating to the eyes.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R11: Highly Flammable.
Safety Statements about 3-(4-Bromophenyl)-1-methoxy-1-methylurea (CAS NO.3060-89-7): 
S16: Keep away from sources of ignition - No smoking.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing. 
RIDADR: UN 1648 3/PG 2 
RTECS: YS3325000

【Transport】
UN 1648 3
【Formulations/Preparations】
50% wettable powder (BASF, Ciba-Geigy). In combination with metolachlor (Galex and Tobacron) or with terbutryn (Ingrater) Ciba-Geigy, 4 lb/gal (400 g/l) flowable (BASF)
Combinations: Igrater 50 WP (metobromuron 25% and terbutryn 25%); Galex 500 EC (metobromuron + metolachlor 1:1 or 2:3)
C 3126
Ciba-3126
PATORAN
Pattonex
【Other Preventative Measures】
Avoid skin and eye contact; prevent drifting.
【Specification】

  The chemical synonyms of 3-(4-Bromophenyl)-1-methoxy-1-methylurea (CAS NO.3060-89-7) are 3-(4-Bromphenyl)-1-methoxyharnstoff ; 3-(p-bromophenyl)-1-methoxy-1-methyl-ure ; C 3126 ; c-3126 ; Metbromuron ; Monobromuron ; n-(4-Bromophenyl)-n’-methyl-n’-methoxy-harnstoff ; n’-(4-bromophenyl)-n-methoxy-n-methyl-ure . It can be used as herbicide.

【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.
Hydrolysis is not recomended as a disposal procedure because of the generation of the toxic products, 3,4-dichloroaniline and dimethylamine.
Metobromuron should be incinerated in a unit operating at 850 deg C with off gas scrubbing equipment. Recommendable method: Incineration.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

PREPARED BY BROMINATION OF N-PHENYL-N'-METHOXY-N'-METHYLUREA: H MARTIN ET AL, SWISS PATENT 405,821 CORRESP TO US PATENT 3,288,851 (BOTH 1966 TO CIBA).
BY BROMINATION OF 1-METHOXY-1-METHYL-3-PHENYLUREA OR BY REACTION OF 4-BROMOPHENYL ISOCYANATE WITH O,N-DIMETHYLHYDROXYLAMINE. ... BRITISH PATENT 965,313; US PATENT 3,223,721.
Reaction of p-bromoaniline with phosgene and N,O-dimethylhydroxylamine (phosgenation/isocyanate addition).
【Usage】
Used on beans, soybeans, tomatoes, tobacco, potatoes, flax, and sunflowers.

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
METOBROMURON IS ABSORBED BY ROOTS AND LEAVES ...
... Different urea herbicides exhibit different mobilities in plant systems. ... Uptake and translocation of chloroxuron, fluometuron, and metobromuron by bean plants when supplied to nutrient cultures in equal concn (essentially equimolar) and specific radioactivities were studied. Whereas the movement of chloroxuron to aerial parts was found to be restricted under the short-term conditions applied, both fluometuron and metobromuron were rapidly translocated into leaves. However, the two latter cmpd differed strikingly with regard to their distribution pattern within the leaves. In contrast to metobromuron, which was mainly confined to tracheal veins, fluometuron had almost completely moved out into the mesophyll tissues. Although no extensive comparisons of the movement of different urea structures are available at this time, it would appear that their apoplastic distribution in plants is regulated in part by the same physical-chemical phenomena which control the mobility and availability of the cmpd in soil.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
... TERRESTRIAL FATE: METOBROMURON DISAPPEARED AT A FASTER RATE THAN FLUOMETURON /FROM SOIL/.
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 470(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that metobromuron should have moderate mobility in soil(SRC). Volatilization of metobromuron should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 3.1X10-9 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(4) and water solubility(5), or from dry soil surfaces(SRC) based on an experimental vapor pressure of 3X10-6 mm Hg(4). Metobromuron may photolyze on soil surfaces(SRC) according to two studies(6,7). A variety of pure culture biodegradation studies, including biodegradation in plants, algae, and fungi(8-11), suggest that metobromuron may biodegrade in water(SRC).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 470(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(1), indicates that metobromuron may adsorb to suspended solids and sediment(SRC) in the water. Metobromuron will be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 3.1X10-9 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(3) and water solubility(4). An estimated BCF value of 38(1,SRC), from an experimental log Kow(2), suggests that metobromuron may bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5). A variety of pure culture biodegradation studies, including biodegradation in plants, algae, and fungi(6-9), suggest that metobromuron may biodegrade in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), metobromuron, which has an experimental vapor pressure of 3X10-6 mm Hg at 25 deg C(2), will exist as a vapor in the ambient atmosphere. Vapor-phase metobromuron 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 about 28 hours(3,SRC). Particulate-phase metobromuron may be physically removed from the air by wet and dry deposition(SRC).

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