Basic information
- CAS
13360-45-7- Standard SMILES
CON(C)C(=O)Nc1ccc(Br)c(Cl)c1- InChIKey
NLYNUTMZTCLNOO-UHFFFAOYSA-N- Molecular formula
- C9H10BrClN2O2
- Average molar mass
- 293.54 g/mol
- Monoisotopic mass
- 291.96142
Overview
Chlorbromuron is a member of ureas.
Names & identifiers
- Preferred name
- Chlorbromuron
- IUPAC
- 3-(4-bromo-3-chlorophenyl)-1-methoxy-1-methylurea
- English name
- CHLORBROMURON
- Molecular formula
- C9H10BrClN2O2
- Molecular weight
- 293.54
Names & synonyms
CHLORBROMURON13360-45-7ChlorobromuronMaloranBromex (herbicide)3-(4-Bromo-3-chlorophenyl)-1-methoxy-1-methylureaCiba 6313DTXSID60402902X2DQC5EHGN'-(4-Bromo-3-chlorophenyl)-N-methoxy-N-methylureaUrea, N'-(4-bromo-3-chlorophenyl)-N-methoxy-N-methyl-C 6313
Show more names
ciba6313MALORAN(R)'LGC' (1401)CHLOROBROMOURONChlorobromourone
C-63131-(3-Chloro-4-bromophenyl)-3-methyl-3-methoxyureaN-(4-Bromo-3-chlorophenyl)-N'-methoxy-N'-methylureaUrea, 3-(4-bromo-3-chlorophenyl)-1-methoxy-1-methyl-DTXCID40202903-(4-bromo-3-chloro-phenyl)-1-methoxy-1-methyl-ureaRefChem:125296236-411-9
Database identifiers
- CAS
13360-45-7- PubChem CID
- 25912
- DTXSID
DTXSID6040290- ChEMBL
CHEMBL1275654- ChEBI
CHEBI:3608
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 41.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 230
Experimental & physicochemical properties
SpringerMaterials PropertiesFusion temperature
Pesticides
Herbicides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Herbicides, Urea Derivative
Pesticide (Chlorbromuron) -> USDA PDB
LogP
Log Kow = 3.09
3.09
OdorMILD ODOR
Density1.68 g/cu cm at 20 °C
Color/Form
WHITE CRYSTALLINE
Off white color, crystalline
Colorless powder
Solubility
SOL IN ACETONE & DIMETHYLFORMAMIDE
SOL IN METHYL ETHYL KETONE, ISOPHORONE, CHLOROFORM, DIETHYL SULFOXIDE
Moderately soluble in xylene.
In water 35 mg/l (20 °C). In acetone 460, dichloromethane 170, hexane 89, benzene 72, isopropanol 12 (all in g/kg, 20 °C).
CorrosivityNONCORROSIVE
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 7.1% (3 of 42) of reports.
Warning
H315 (92.9%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P317, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information2002/2076
Hazards Summary
Urea-derived herbicides have low toxicity in animal feeding studies; May induce methemoglobinemia; No effect level in 90-day feeding studies of rats and dogs was 316 mg/kg diet; No significant dermal absorption; A skin and eye irritant; [HSDB] Systemic toxicity unlikely unless large amounts ingested; [EPA Pesticides, p. 122] An irritant; [MSDSonline]
FIFRA RequirementsTolerances for residues removed.
Hazard Classes and CategoriesSkin Irrit. 2 (92.9%)
Skin, Eye, and Respiratory IrritationsSkin and eye irritant.
Safety & protection
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.
Chemistry & industry
Pharmacology
Mechanism of Action
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.
Metabolism/Metabolites
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.
Absorption, Distribution and Excretion
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.
Uses & manufacturing
Uses
Used as a selective pre- and post-emergence herbicide for control of annual grasses and broad-leaved weeds in potatoes, legumes, cereals, and other crops; US production discontinued; [HSDB]
Farming (Pesticides) [Category: Industry]
Used as an herbicide in corn, soybean, potato, wheat, and carrot /fields/. /Former use/
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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