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Home > Encyclopedia > 3-(4-Chlorophenyl)-1,1-dimethylurea

3-(4-Chlorophenyl)-1,1-dimethylurea

3-(4-Chlorophenyl)-1,1-dimethylurea structure

3-(4-Chlorophenyl)-1,1-dimethylurea 

structure
  • CAS No:

    150-68-5

  • Formula:

    C9H11ClN2O

  • Chemical Name:

    3-(4-Chlorophenyl)-1,1-dimethylurea

  • Synonyms:

    Urea,N′-(4-chlorophenyl)-N,N-dimethyl-;Urea,3-(p-chlorophenyl)-1,1-dimethyl-;N′-(4-Chlorophenyl)-N,N-dimethylurea;N-(p-Chlorophenyl)-N′,N′-dimethylurea;1-(p-Chlorophenyl)-3,3-dimethylurea;3-(p-Chlorophenyl)-1,1-dimethylurea;3-(4-Chlorophenyl)-1,1-dimethylurea;CMU;1,1-Dimethyl-3-(p-chlorophenyl)urea;Karmex Monuron Herbicide;Karmex W. monuron herbicide;Monuron;Telvar;Telvar Monuron Weedkiller;Telvar W. monuron weedkiller;N,N-Dimethyl-N′-(4-chlorophenyl)urea;N-(4-Chlorophenyl)-N′,N′-dimethylurea;1-(4-Chlorophenyl)-3,3-dimethylurea;1,1-Dimethyl-3-(4-chlorophenyl)urea;NSC 8949;N′-p-Chlorophenyl-N,N-dimethylurea;Chlorfenidim

  • Categories:

    Agrochemicals  >  Herbicides

Description

White, crystalline solid; odorless. Very low solubility in water and hydrocarbonsolvents; slightly soluble in oils; partially soluble inalcohols; stable toward oxidation and moisture.ChEBI: 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.White crystalline solid or white powder with a slight odor. Melting point 175°C. Moderately toxic by ingestion. Used as an herbicide.


Monuron appears as white crystalline solid or white powder with a slight odor. Melting point 175°C. Moderately toxic by ingestion. Used as an herbicide.


Monuron appears as white crystalline solid or white powder with a slight odor. Melting point 175°C. Moderately toxic by ingestion. Used as an herbicide.|Monuron is a member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas 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. It has a role as a herbicide, a xenobiotic and an environmental contaminant. It is a member of monochlorobenzenes and a 3-(3,4-substituted-phenyl)-1,1-dimethylurea.

3-(4-Chlorophenyl)-1,1-dimethylurea Basic Attributes

198.65

198.65

2097922

205-766-1

I99GAK5X1D

8949

3077|2588

DTXSID0020311

WHITE PLATES FROM METHANOL|THIN RECTANGULAR PRISMS FROM METHANOL|Platelets

29242990

Characteristics

32.3

1.94 (est)

White Crystalline Solid

1.27 g/cm3 @ Temp: 20 °C

170.5-171.5 °C

365 to 392° F at 760 mm Hg (decomposes) (NTP, 1992)

170.8±25.7 °C

1.5330 (estimate)

Sol in benzene: 3 g/kg at 27 deg C

0-6°C

0.067 mPa @ 25 deg C

Oral-Rat LD50: 1053 mg/kg; Oral-Mouse LD50: 1920 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

SLIGHT ODOR

6.26 SATURATED AQ SOLUTION

Henry's Law constant= 5.72X10-10 atm-cu m/mole (est).

COMMERCIAL PRODUCT MELTS @ 176-177 °C|VAPOR PRESSURE: 178X10-5 MM HG @ 100 °C|DECOMP @ 185-200 °C|The rate of hydrolysis at room temp and pH 7 is negligible ... .|... Used at 10-15 kg/ha for total weed control of uncropped areas. /Monuron Trichloroacetate/

Insoluble in water. Is hydrolyzed slowly by acids and alkalis, and more rapidly on heating (NTP, 1992).

Amides and Imides

MONURON 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).

NON-CORROSIVE

Safety Information

III

9

UN 3077 9/PG 3

3

22-40-50/53

36/37-60-61

YS6300000

Xn,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable toward oxygen and moisture under ordinary conditions at neutral pH.

P273-P281-P501

H302-H351-H410

Treatment at elevated temp by acid or base yields dimethylamine and 3,4-dichloroaniline. Hydrolysis is not recommended as a disposal procedure because of the generation of the toxic product, 3,4-dichloraniline and dimethylamine. Recommendable method: Incineration. Not recommendable method: Hydrolysis. Peer review: Incineration in a unit with effluent gas scrubbing is recommendable. (Peer-review conclusions of an IRPTC expert consultation May 1985))

DHHS/NTP; Toxicology & Carcinogenesis Studies of Monuron in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 266 (1988) NIH Publication No. 88-2522

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, and P501|P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures away from acids and alkalies. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|PROTECT SKIN & HAIR ... USE ONLY APPROVED RESPIRATORY PROTECTIVE EQUIPMENT, WHEN LABEL DIRECTIONS ADVISE NEED. /HERBICIDES/|Wear rubber gloves for all handling.

... NON-FLAMMABLE.

Self-contained breathing apparatus, rubber gloves, hats, suits, and boots must be worn.

AVOID INHALING ANY DUST, SPRAY MIST & STRONG VAPOR. /HERBICIDES/

Toxicity

moderately toxic

IN PRESENCE OF MODERATE AMT OF CARBARYL, DEGRADATION /OF MONURON IN COTTON PLANTS/ BEYOND MONO-DEMETHYLATION WAS INHIBITED. ... 4-BENZOTHIOPHENE-N-METHYLCARBAMATE WAS AS EFFECTIVE AS CARBARYL.|FLAVINS (FLAVINMONONUCLEOTIDE) HAVE BEEN SHOWN TO CAUSE PHOTOINACTIVATION OF PHENYLUREAS, SUCH AS MONURON, IN VITRO.

LD50 Rat oral 3600 mg monuron/kg|In diet: rats and dogs: no effect level: 250-500 ppm

Carcinogenesis studies of monuron (greater than 99% pure), ... were conducted by feeding diets containing 0, 750, or 1,500 ppm monuron to groups of 50 F344/N rats of each sex ... for 103 wk. Survivors then were fed a control diet for 1 week, killed, and examined. Throughout most of the studies, mean body weights of dosed rats of each sex were lower than those of the controls. Survival rates of low dose female rats ... were increased relative to those of the controls. Nonneoplastic changes associated with the long-term administration of monuron to rats included renal tubular cell cytomegaly, mainly involving the proximal convoluted tubules in male and female rats, and dose-related hepatic cytoplasmic changes in male rats.In the 104 wk study, the kidneys and liver of male rats were the primary tissues affected. Under the conditions of these 2 yr feed studies, there was clear euidence of carcinogenicity for male F344/N rats in that monuron caused increased incidences of tubular cell adenocarcinomas of the kidney, tubular cell adenomas of the kidney, and neoplastic nodules or carcinomas (combined) of the liver. Monuron induced cytomegaly of the renal tubular epithelial cells in both male and female F344/N rats.|Carcinogenesis studies of monuron (greater than 99% pure), ... were connducted by feeding diets containing ... 0, 5000, or 10000 ppm to groups of 50 B6C3F1 mice of each sex for 103 weeks. Survivors then were fed a control diet for 1 week, killed, and examined. Throughout most of the studies, mean body weights of dosed ... mice of each sex were lower than those of the controls. Survival rates of ... high dose male and female mice were increased relative to those of the controls. In male mice, dose-related decreases occurred in the incidences of hepatocellular carcinomas (6/50 5/49; 2/50) and hepatocellular adenomas or carcinomas (12/50; 8/49; 6/50); incidences of hepatocellular tumors in low dose female mice were reduced, but the decreases were not dose related. The incidences of malignant lymphomas were reduced in dosed female mice (16/50; 8/50; 7/50). Under the conditions of these 2 year feed studies ... there was no evidence of carcinogenicity for female F344/N rats or for male or female B6C3FI mice. Monuron was not mutagenic in Salmonella strains TA98, TA100, TA1535, or TA1537 in the presence or absence of Aroclor 1254 induced rat liver S9. Monuron did induce chromosomal aberrations and sister chromatid exchanges in cultured Chinese hamster ovary cells.

Monuron is not known to occur naturally(1).

Since monuron is commercially produced and used as a herbicide(1), it will be released to the environment during the manufacture and particularly during the use of the herbicide(SRC). Accidental spills during loading/unloading and shipment will also release monuron in the environment(SRC).

TERRESTRIAL FATE: Biodegradation appears to be the major process by which monuron may be lost from most soils(1-2). The loss of monuron from soil surface by photolysis may account for a small fraction of loss of monuron as most of the monuron would move deeper into soil with rain(1). Volatilization loss of monuron from dry soil or wet soils should not be important(1). Monuron may moderately leach in most soils(3-4). Depending on the nature of soil and climatic conditions, the field half-life of monuron in soil range from less than 30 days to 166 days(5-7).|AQUATIC FATE: At low concns (on the order of ug/l), the major process for the loss of monuron from water appears to be biodegradation(1-2). Neither hydrolysis nor any other chemical reaction is important for the loss of monuron in water(1,3). Monuron may photolyze in surface layers of water where sunlight penterates(1). The photolysis half-life of monuron in aqueous solution by natural sunlight is estimated to be 15 days(4). Photolysis is accelerated by the presence of surfactants(5). Based upon the low vapor pressure(6) and high water solubility(7), monuron should not volatilize from water. Monuron is not expected to bioconcentrate in aquatic organisms(7).|ATMOSPHERIC FATE: Based upon on its vapor pressure, 5.03X10-7 mm Hg at 25 °C(1), monuron is expected to be present partially in the vapor phase and partially in the particulate form in air(2,SRC). Vapor phase monuron will react with photochemically produced hydroxyl radicals with a half-life of 6.7 hr(3-4). Monuron may also be removed from the atmosphere by dry and wet deposition(SRC).

Monuron was stable in sterile aqueous solution at pH values normally found in natural waters(1). solution of monuron in the dark was found to be stable towards chemical reactions(2). The disappearance of monuron in soil by non-biological degradation was concluded to be unimportant in most cases(2). When a 88.3 ppm aqueous solution of monuron was exposed to sunlight, 83% loss was observed in 48 days(2). The half-life for the photodegradation of aqueous solution of monuron in natural sunlight has been estimated to be 15 days(5). Addition of surfactants enhanced the photolysis rate of monuron in solution(3). Five substituted biphenyl photoproducts were identified from the photolysis of monuron(4). Besides these biphenyl photoproducts, demethylated, completely monodemethylated, and a phenolic product, 3-(2-hydroxy-4-chlorophenyl)-1,1-dimethylurea have been isolated as photoproducts of monuron(6-7).|Based on an estimation method(1-2), the rate constant for reaction of monuron with hydroxyl radicals in the atmosphere is 3.8X10-11 cu cm/molecule-sec(SRC). If the 12 hr daylight average concentration of hydroxyl radicals in the atmosphre is assumed to be 1.5X10-6 radicals/cu cm(1), the half-life of this reaction would be 6.7 hr(SRC).|The 4-halogen substituent was replaced by hydroxyl when linuron and monuron wereexposed to sunlight in aqueous solutions; demethylation also occured. Monuron, on irradiation in water under aerobic conditions, gives 3-(4-chloro-2-hydroxyphenyl)-1,1-dimethylurea, together with 1,3-bis(p-chlorophenyl)urea and a number of oxidized and polymeric compounds. 1,3-Bis(p-chlorophenyl)urea may be formed by a reaction which proceeds via an ioscyanate intermediate; dimethylamine is eliminated from monuron to form p-chlorophenyl isocyanate, which can react with free p-chloroaniline.|When incubated with the fungus Cunninghamella echinulata Thaxter, monuron yielded 3-(4-chlorophenyl-methylurea and 4-chlorophenylurea.|For more Environmental Abiotic Degradation (Complete) data for MONURON (6 total), please visit the HSDB record page.

From its water solubility and a regression equation, the bioconcentration factor (BCF) for monuron in aquatic organisms has been estimated to be 29(1). Based on a log Kow value of 1.94(2) and a regression equation(3), the BCF value can be estimated to be 17(SRC). Both these values indicate that bioconcentration of monuron in aquatic organisms should not be important(1,SRC). The low rate of uptake and fast depuration (depuration half-life of 0.45 days) of monuron from catfish (Ictalurus melas)(4) also indicates that bioconcentration will not be important(SRC).

89.13 L/kg|The Koc values for monuron determined from experimental adsorption isotherms or estimated using recommended regression equations range from 83 to 225(1-6). According to a suggested classification scheme(9), Koc values of this magnitude indicate that monuron is moderately to highly mobile in soil. Soil thin layer chromatographic studies also indicate that monuron is moderately mobile in soil(5,7). The adsorption of monuron in soil is virtually independent of pH and clay content of soil, but the adsorption increases with increase in organic carbon content(6,8). However, other investigators concluded that the adsorption of monuron increases with an increase in the clay content of soil(10).

Volatilization from water should not be important transport process for monuron. Based on a value of Henry's Law constant of 5.72X10-10 atm-cu m/mole estimated from the ratio of vapor pressure(2) and water solubility(1), the volatilization half-life of monuron from a 1 m deep model river flowing at a speed of 1 m/sec and a wind speed of 5 m/sec is estimated to be about 165 yr(3,SRC). If the effect of sorption is considered, the half-life will be even longer. The volatilization half-life of monuron from 1 to 10 cm soil depth has been estimated to be about 160-170 days(4). The volatilization of monuron coevaporating with water vapor in soil was found to be insignificant(5). Therefore, the loss of monuron due to volatilization from both dry and wet soil should not be an important environmental fate process(SRC).

GROUNDWATER: Monuron was detected in one groundwater sample from a rural area in Ontario, Canada that was contaminated with the herbicide as a result of a spill(1).

IN RATS GIVEN 875 MG/KG BODY WT ORALLY, ... MONURON RELATED MATERIAL WAS ... SECRETED INTO MILK OF LACTATING ANIMALS.

Monuron is not registered for use in the U.S. and therefore there should be no exposure of monuron by field applicators and formulators(SRC). If monuron is manufactured for export, occupational exposure of workers involved in manufacturing and loading monuron would most likely be through dermal contact. (SRC)

Drug Information

SUBSTITUTED UREAS ARE READILY ABSORBED BY PLANT ROOTS & TRANSLOCATED TO ACCUMULATE IN LEAVES ... THEY DO NOT PENETRATE READILY THROUGH LEAVES.|AFTER ADMIN OF 175 MG/KG BODY WT/DAY FOR 60 DAYS OR OF 0.1-20.0 MG/KG BODY WT FOR 6 MO, TISSUE RETENTION OF MONURON-RELATED SUBSTANCES OCCURRED /MOST/ IN LUNGS, /DECR RESPECTIVELY IN/ HEART, LIVER, BRAIN & KIDNEYS, MILK, BONE MARROW & THYROID GLAND.|IN RATS GIVEN 875 MG/KG BODY WT ORALLY, PEAK BLOOD CONCN OCCURRED 2 HR AFTER DOSING ... CMPD WAS DISTRIBUTED EVENLY THROUGHOUT BODY.

3-(P-CHLOROPHENYL)-1,1-DIMETHYLUREA YIELDS IN COTTON 3-(P-CHLOROPHENYL)-1-HYDROXYMETHYL-1-METHYLUREA; ALSO YIELDS 3-(P-CHLOROPHENYL)-1-METHYLUREA. /FROM TABLE/|COTTON PLANTS DEGRADED MONURON TO MONOMETHYLMONURON & P-CHLORO-PHENYLUREA BY SUCCESSIVE DEMETHYLATIONS & THEN TO P-CHLOROANILINE BY HYDROLYSIS OF AMIDE BOND.|IN MAMMALS, MONURON IS METABOLIZED (I) BY OXIDATIVE N-DEMETHYLATION, (II) BY HYDROXYLATION OF AROMATIC NUCLEUS & (III) BY FISSION OF UREA RESIDUE TO GIVE CHLOROANILINE DERIVATIVES.|YIELDS OF VARIOUS METABOLITES INDICATE THAT HYDROXYLATION FAVORS 2-POSITION RATHER THAN 3-POSITION. PHENOLIC METABOLITES WERE EXCRETED IN URINE AS CONJUGATES. 4-CHLORO-2-HYDROXYANILINE WAS EXCRETED AS THE N-ACETYL CMPD 2-ACETAMINO-5-CHLOROPHENOL.|For more Metabolism/Metabolites (Complete) data for MONURON (10 total), please visit the HSDB record page.

SUBSTITUTED UREAS ... IN LEAVES ... CAUSE COLLAPSE OF PARENCHYMA VESSELS. ... THEY INHIBIT PHOTOSYNTHESIS ... AND ARE POWERFUL INHIBITORS OF OXIDATION OF WATER TO OXYGEN (HILL REACTION) ... SUGGESTED THAT MONURON BLOCKS PHOTOSYNTHESIS AT SITE OF ELECTRON TRANSFER BY FLAVIN MONONUCLEOTIDE ... .

SYMPTOMS: Symptoms of exposure to this compound may include fall in blood pressure, convulsions or coma. Other symptoms may include ataxia, drowsiness, hyporeflexia, pallor, tachypnea, dacryorrhea, aciduria, diarrhea, epistaxis, hyperreflexia and irritability. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits very toxic fumes of nitrogen oxides and chlorine. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

1. SKIN CONTAMINATION SHOULD BE REMOVED PROMPTLY BY WASHING WITH SOAP AND WATER. CONTAMINATION OF THE EYES SHOULD BE TREATED IMMEDIATELY BY PROLONGED FLUSHING OF THE EYES WITH COPIOUS AMOUNTS OF CLEAN WATER. IF DERMAL OR OCULAR IRRITATION PERSISTS, MEDICAL ATTENTION SHOULD BE OBTAINED WITHOUT DELAY. /OTHER HERBICIDES/|2. INGESTIONS OF THESE HERBICIDES ARE LIKELY TO BE FOLLOWED BY VOMITING AND DIARRHEA DUE TO THE IRRITANT PROPERTIES OF MOST OF THE TOXICANTS. ... A. IF LARGE AMOUNTS OF HERBICIDE HAVE BEEN INGESTED, AND IF THE PATIENT IS FULLY ALERT, INDUCE EMESIS WITH SYRUP OF IPECAC, FOLLOWED BY SEVERAL GLASSES OF WATER. DOSAGE FOR ADULTS AND CHILDREN OVER 12 YEARS: 30 ML; DOSAGE FOR CHILDREN UNDER 12 YEARS 15 ML. WHEN VOMITING HAS STOPPED, GIVE ACTIVATED CHARCOAL. ADD SORBITOL TO THE CHARCOAL SLURRY UNLESS DIARRHEA HAS ALREADY COMMENCED. IF, FOR SOME REASON, THE PATIENT IS NOT FULLY ALERT, PUT IN PLACE A CUFFED ENDOTRACHEAL TUBE TO PROTECT THE AIRWAY, THEN ASPIRATE AND LAVAGE THE STOMACH WITH A SLURRY OF ACTIVATED CHARCOAL. LEAVE A QUANTITY OF CHARCOAL, WITH SORBITOL, IN THE STOMACH BEFORE WITHDRAWING THE STOMACH TUBE. REPEATED ADMINISTRATION OF CHARCOAL AT HALF OR MORE THE INITIAL DOSAGE EVERY 2-4 HOURS MAY BE BENEFICIAL. /OTHER HERBICIDES/|2. B. IF THE AMOUNT OF INGESTED HERBICIDES WAS SMALL, IF EFFECTIVE EMESIS HAS ALREADY OCCURRED, OR IF TREATMENT IS DELAYED, ADMINISTER THE ACTIVATED CHARCOAL AND SORBITOL BY MOUTH. C. IF SERIOUS DEHYDRATION AND ELECTROLYTE DEPLETION HAVE OCCURRED AS A RESULT OF VOMITING AND DIARRHEA, MONITOR BLOOD ELECTROLYTES AND AND FLUID BALANCE AND ADMINISTER INTRAVENOUS INFUSIONS OF GLUCOSE, NORMAL SALINE RINGER'S SOLUTION, OR RINGER'S LACTATE TO RESTORE EXTRACELLULAR FLUID VOLUME AND ELECTROLYTES. FOLLOW THIS WITH ORAL NUTRIENTS AS SOON AS FLUIDS CAN BE RETAINED. FLUIDS SERVE TO SUPPORT EXCRETION OF THE TOXICANTS. D. SUPPORTIVE MEASURES ARE ORDINARILY SUFFICIENT FOR SUCCESSFUL MANAGEMENT OF EXCESSIVE EXPOSURES TO THESE HERBICIDES. /OTHER HERBICIDES/

chlorophenyl dimethylurea

3-(4-Chlorophenyl)-1,1-dimethylurea Use and Manufacturing

Methods of Manufacturing

REACTION OF P-CHLOROPHENYL ISOCYANATE WITH DIMETHYLAMINE|PREPD BY REACTING P-CHLOROPHENYL ISOCYANATE WITH DIMETHYLAMINE|p-Chloroaniline in dioxane or another inert solvent with anhydrous hydrogen chloride and phosgene at 70-75 °C forms p-chlorophenyl isocyanate, which at 25 °C with dimethylamine gives monuron.

Uses

Herbicide, sugarcane-flowering suppressant.

Production

(1971) 3.7X10+7 G (CONSUMPTION)|(1975) 9.1X10+7 G (CONSUMPTION)

100% AS HERBICIDE FOR USE ON CROPS (1971)

WETTABLE POWDER (80% ACTIVE COMPONENT); WATER SUSPENSION 2.8 LB/GALLON ACTIVE INGREDIENT.|Wettable powder (800 g monuron/kg). Mixtures include: Urox, granular (55, 110 or 220 g monuron-TCA/kg), oil miscible liquid, oil/water miscible concentrate oil/water miscible concentrate, (monuron-TCA + 2,4-D)>.|(Monuron +) amitrole.|Monuron is available in the US as a technical grade product, as a wettable powder containing @ 80% of the chemical and as granular formulations containing 2.4-8%. Granular formulations containing both monuron and trichloroacetic acid are also available, with several concentrations of each ai.

Urea, N'-(4-chlorophenyl)-N,N-dimethyl-: ACTIVE|RESIDUES OF 1-7 MG/KG WERE TOLERATED ON ... FRUITS & VEGETABLES. AS OF JULY 1973 ... MONURON IS NO LONGER REGISTERED FOR USE ON ANY AGRICULTURAL CROP (US EPA, 1975).|... DIFFERENTIAL METAB IS ONE OF MAJOR FACTORS RESPONSIBLE FOR SELECTIVITY OF PHENYLUREA HERBICIDES. IN PARTICULAR, COTTON EXHIBITED REMARKABLE ABILITY TO DEGRADE MONURON ... IN CONTRAST TO CERTAIN MONOCOTYLEDONOUS PLANT SPECIES ... DIFFERENCES IN METAB ... BASED ON DIFFERENT RATES OF DEGRADATION AND NOT ON DIFFERENCES IN BIOCHEMICAL TRANSFORMATION PATHWAYS.|IT IS RECOMMENDED @ 10 TO 30 KG AI/HA FOR TOTAL WEED CONTROL OF NON-CROP AREAS; 5 TO 10 KG AI/HA SUFFICES FOR ANNUAL MAINTENANCE.

PRODUCT ANALYSIS IS BY HYDROLYSIS AND TITRATION OF THE 4-CHLOROANILINE WITH PERCHLORIC ACID. RESIDUE ANALYSIS IS BY ALKALINE HYDROLYSIS, AND COLORIMETRIC DETERMINATION OF THE 4-CHLOROANILINE, BY GLC AND HPLC.|RAPID BIOLUMINESCENCE METHOD CAPABLE OF DETERMINING LOW CONCN OF PHOTOSYNTHESIS-INHIBITING HERBICIDES, SUCH AS MONURON, IN WATER & SOIL ... .|Sample matrix: Specified fruit and vegetables. Sample preparation: Alkaline hydrolysis to release para-chloroaniline; diazotize; couple with N-(1-naphthyl) ethylene-diamine; clean-up and separate resulting dyes on cellulose column. Assay procedure: TLC.|Sample matrix: Residues. Sample preparation: Hydrolyse to para-chloroaniline using sodium hydroxide; distil; acidify distillate; wash with hexane or dichloromethane; neutralize; extract with hexane. Assay procedure: GC with FID.|For more Analytic Laboratory Methods (Complete) data for MONURON (7 total), please visit the HSDB record page.

Agrochemicals -> Herbicides|Herbicides

Computed Properties

Molecular Weight:198.65
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:198.0559907
Monoisotopic Mass:198.0559907
Topological Polar Surface Area:32.3
Heavy Atom Count:13
Complexity:177
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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