MONURON

MONURON Basic information
Product Name:MONURON
Synonyms:N,N-Dimethyl-N'-(4-chlorophenyl)urea;n,n-dimethyl-n’-(4-chlorophenyl)urea;n’-(4-chlorophenyl)-n,n-dimethyl-ure;TELVAR(R);N-(4-CHLOROPHENYL)-N,N'-DIMETHYLUREA;Monurex;MONURON;1-(4-Chloro phenyl)-3,3-dimethyluree
CAS:150-68-5
MF:C9H11ClN2O
MW:198.65
EINECS:205-766-1
Product Categories:Alphabetic;Alpha sort;Herbicides;H-MAlphabetic;M;METI - MZPesticides&Metabolites;Pesticides&Metabolites;Urea structure
Mol File:150-68-5.mol
MONURON Structure
MONURON Chemical Properties
Melting point 173-174 °C (lit.)
Boiling point 301.31°C (rough estimate)
density 1,27 g/cm3
vapor pressure 0Pa at 20℃
refractive index 1.5330 (estimate)
storage temp. 0-6°C
pka14.22±0.70(Predicted)
form Crystalline Solid
color White
Water Solubility 262mg/L(25 ºC)
λmax244nm(H2O)(lit.)
Merck 14,6261
BRN 2097922
LogP1.94 at 20℃
IARC3 (Vol. Sup 7, 53) 1991
EPA Substance Registry SystemMonuron (150-68-5)
Safety Information
Hazard Codes Xn,N
Risk Statements 22-40-50/53
Safety Statements 36/37-60-61
RIDADR UN 3077 9/PG 3
WGK Germany 3
RTECS YS6300000
TSCA Yes
HazardClass 9
PackingGroup III
HS Code 29242990
Hazardous Substances Data150-68-5(Hazardous Substances Data)
ToxicityLD50 orally in rats: 3700 mg/kg (Bailey, White)
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
MONURON Usage And Synthesis
Chemical PropertiesWhite, crystalline solid; odorless. Very low solubility in water and hydrocarbonsolvents; slightly soluble in oils; partially soluble inalcohols; stable toward oxidation and moisture.
UsesMonuron may be used as a reference standard in the determination of monuron in rice and corn using high performance liquid chromatography coupled with fluorescence detection combined with ultraviolet decomposition and post-column derivatization.
UsesHerbicide, sugarcane-flowering suppressant.
DefinitionChEBI: A member of the class of ureas that is urea in which one of the nitrogens is substituted by a p-chlorophenyl group while the other is substituted by two methyl groups.
General DescriptionWhite crystalline solid or white powder with a slight odor. Melting point 175°C. Moderately toxic by ingestion. Used as an herbicide.
Air & Water ReactionsInsoluble in water. Is hydrolyzed slowly by acids and alkalis, and more rapidly on heating .
Reactivity ProfileMONURON is a chlorinated urea derivative. May react with azo and diazo compounds to generate toxic gases. May react with strong reducing agents to generate flammable gases. Reacts as a weak base. Combustion generates mixed oxides of nitrogen (NOx).
HazardQuestionable carcinogen.
Health HazardToxic properties are similar to Diuron; hydro-lyzes under acidic or alkaline conditions top-chloroaniline, which can cause anemia andmethemoglobinemia; LD50 data published inthe literature differ; acute and chronic tox-icity of this herbicide is probably of loworder; no reported case of human poisoning; showed clear evidence of carcinogenicity in male F344/N rats fed diets containing 750 ppm monuron for 2 years; causedcancers in the kidney and liver (NationalToxicology Program 1988); female rats andmale and female mice (B6C3F1) showed noevidence; induced cytomegaly of the renalepithelial cells in rats.
LD50 oral (rat): 3700 mg/kg (Bailey andWhite, 1965)
LD50 oral (rat): 1053 mg/kg (Lewis 1995).
Fire HazardFlash point data for MONURON are not available; however, MONURON is probably combustible.
Flammability and ExplosibilityNotclassified
Safety ProfileModerately toxic by ingestion, intraperitoneal, and possibly other routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. An herbicide. When heated to decomposition it emits very toxic fumes of NOx and Cl-.
Environmental FateBiological. Monuron was mineralized in sewage samples obtained from a water treatment plant in Ithica, NY. (4-Chlorophenyl)urea and 4-chloroaniline were tentatively identified as metabolites (Wang et al., 1985).
Soil/Plant. In soils and plants, monuron is demethylated at the terminal nitrogen atom coupled with ring hydroxylation forming 3-(2-hydroxy-4-chlorophenyl)urea and 3-(3- hydroxy-4-chlorophenyl)urea (Hartley and Kidd, 1987). Walln?efer et al. (197
Photolytic. When an aqueous solution of monuron was exposed to sunlight or simulated sunlight, the major degradative pathways observed were the photooxidation and demethylation of the N-methyl groups (Crosby and Tang, 1969; Tanaka et al., 1982a),
Tanaka et al. (1981) studied the photolysis of monuron in dilute aqueous solutions in order to fully characterize a substituted diphenylamine that was observed in an earlier investigation (Tanaka et al., 1977). They identified this compound as an isomeric mixture containing 92% 2-chloro-4¢,5-bis(N¢,N¢-dimethylureido)biphenyl and 8% 5-chloro-2,4¢- bis(N¢,N¢-dimethylureido)biphenyl (Tanaka et al., 1981).
Tanaka et al. (1982) undertook a study to identify the several biphenyls formed in earlier photolysis studies (Tanaka et al., 1979, 1981). They identified these compounds as 2,4¢-, 3,4¢- and 4,4¢-bis-(N¢,N¢-dimethylureido)biphenyls (fenuron biphenyls) (Ta



Purification MethodsCrystallise monuron from MeOH. [Beilstein 12 IV 1191.]
MONURON Preparation Products And Raw materials
Preparation ProductsN,N-Dimethylcarbamic acid
N-(4-CHLOROPHENYL)-2,3-DIHYDRO-4H-1,4-BENZOTHIAZINE-4-CARBOXAMIDE AURORA 11845 METHAZOLE 1-(3,4-DICHLOROPHENYL)-3-METHYL-3-PHENYLUREA Diuron AURORA 11827 MONURON N-(4-CHLOROPHENYL)-4-[1-METHYL-6-(METHYLAMINO)-3,5-DINITRO-1,4-DIHYDRO-2-PYRIDINYL]TETRAHYDRO-1(2H)-PYRAZINECARBOXAMIDE N-(4-CHLOROPHENYL)-4-(6-CHLORO-2-PYRIDINYL)TETRAHYDRO-1(2H)-PYRAZINECARBOXAMIDE N-(3,4-DICHLOROPHENYL)(4-(N-(3,4-DICHLOROPHENYL)CARBAMOYL)PIPERAZINYL)FORMAMIDE N-(4-CHLOROPHENYL)(4-(3-CHLORO-5-(TRIFLUOROMETHYL)(2-PYRIDYL))PIPERAZINYL)FORMAMIDE N1-(4-CHLORO-3-NITROPHENYL)PIPERIDINE-1-CARBOXAMIDE N1-(4-CHLORO-3-NITROPHENYL)PYRROLIDINE-1-CARBOXAMIDE 7-CHLORO-N-(4-CHLOROPHENYL)-2,3-DIHYDRO-4H-1,4-BENZOTHIAZINE-4-CARBOXAMIDE NEBURON N4-(4-CHLORO-3-NITROPHENYL)MORPHOLINE-4-CARBOXAMIDE 3-(4-chlorophenyl)-1,1-dimethyluronium trichloroacetate monuron-TCA,MONURON TCA AURORA 11742

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