Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > Monolinuron

Monolinuron

Monolinuron structure

Monolinuron 

structure
  • CAS No:

    1746-81-2

  • Formula:

    C9H11ClN2O2

  • Chemical Name:

    Monolinuron

  • Synonyms:

    Urea,N′-(4-chlorophenyl)-N-methoxy-N-methyl-;Urea,3-(p-chlorophenyl)-1-methoxy-1-methyl-;N′-(4-Chlorophenyl)-N-methoxy-N-methylurea;Aresin;3-(4-Chlorophenyl)-1-methoxy-1-methylurea;N-4-Chlorophenyl-N′-methyl-N′-methoxyurea;Monolinuron;Arezine;N-(4-Chlorophenyl)-N′-methoxy-N′-methylurea;N′-(4-Chlorophenyl)-N-methyl-N-methoxyurea;3-(4-Chlorophenyl)-1-methyl-1-methoxyurea;Arezin;Monorotox;N-Methyl-N-methoxy-N′-(4-chlorophenyl)urea;1-Methoxy-1-methyl-3-(4-chlorophenyl)urea;56449-36-6

  • Categories:

    Agrochemicals  >  Herbicides

Description

COLOURLESS CRYSTALS.


COLOURLESS CRYSTALS.


Monolinuron is a member of ureas.

Monolinuron Basic Attributes

214.65

214.65

217-129-5

6KJJ4XAD6M

1273

DTXSID0037576

COLORLESS CRYSTALS

29280000

Characteristics

41.6

2.2

1.3575 (rough estimate)

80-83 °C

100 °C

1.5790 (estimate)

Solubility in water: none

0-6°C

Vapour pressure, Pa at 22°C: 0.02

Oral-Rat LD50: 1800 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

ODORLESS

142.9 Ų [M+H]+ [CCS Type: TW]

NONCORROSIVE

Safety Information

UN30779/PG3

3

22-48/22-50/53

22-60-61

YS6425000

Xn,N

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

STABLE AT MELTING POINT & IN SOLN BUT SLOWLY DECOMPOSES IN ACIDS & BASES

P273-P501

H302-H373-H410

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.|Monolinuron should be incinerated in a unit operating at 850 °C equipped with off gas scrubbing equipment. Recommendable methods: Incineration ... .

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion if formulations contain flammable/explosive solvents.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P273, P301+P312, P314, P330, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 197 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Use water spray, powder, foam, carbon dioxide.

Do NOT wash away into sewer. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Personal protection: chemical protection suit including self-contained breathing apparatus.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs.

Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.

The substance may have effects on the blood. This may result in anaemia.

NO open flames.

PREVENT DISPERSION OF DUST! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN!

Use local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

IN SOIL IT DEGRADES TO 5.6% WITHIN 3 MO & TO LESS THAN 0.2% WITHIN 10 MO...|Duration of residual activity in soil is about 3-4 months (at 3 kg/ha).

Toxicity

moderately toxic

Monolinuron's production and use as a herbicide(1) will result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), measured Koc values ranging from 40(3) to 2025(11) indicates monolinuron should have medium mobility in soil(SRC). Volatilization of monolinuron should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 4.6X10-8 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(4) and water solubility(5). Volatilization is not expected from dry soil surfaces either(SRC) based on an experimental vapor pressure of 1.5X10-4 mm Hg(4). Half-lives for monolinuron in soil have been determined to be 60 days(2) and 33-66 days(6). According to biodegradation studies using mixed bacterial cultures(7-9), monolinuron is expected to biodegrade in soil(SRC). Photolysis of monolinuron should occur on soil surfaces(SRC) according to its degradation by light at wavelengths greater than 290 nm(10).|AQUATIC FATE: Based on a recommended classification scheme(1), measured Koc values ranging from 40(2) to 2025(13) indicate that monolinuron may adsorb to suspended solids and sediment(SRC) in water. Monolinuron will be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 4.6X10-8 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(3) and water solubility(4). Experimental BCF values ranging from <20 to 140(5-7), suggest that monolinuron will undergo moderate to high bioconcentration in aquatic organisms(SRC), according to a recommended classification scheme(8). The half-life of monolinuron in water has been determined to be 22 days(9). According to biodegradation studies using mixed bacterial cultures(10-12), monolinuron is expected to biodegrade in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), monolinuron, which has an experimental vapor pressure of 1.5X10-4 mm Hg at 25 °C(2), will exist as a vapor in the ambient atmosphere. Vapor-phase monolinuron 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 27 hours(3,SRC). Particulate-phase monolinuron may be physically removed from the air by wet and dry deposition(SRC).

Degradation is accelerated by UV light.|The rate constant for the vapor-phase reaction of monolinuron with photochemically produced hydroxyl radicals has been estimated as 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 27 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Degradation of monolinuron by light at wavelengths greater than 290 nm was 38.3% after 17 hours(2).

14.13|Bioaccumulation tests using activated sludge, algae, and fish (golden ide) gave BCF values for monolinuron of 70 (5-day), 40 (1-day), and 20 (3-day), respectively(1). The BCF for monolinuron has been estimated to be 17 and 10 based on water solubility and Koc, respectively(2). Another BCF value monolinuron was calculated to be 22(3). The experimental BCF value of monolinuron in the algae Chloroella was 33 after exposure to 50 ug/l for 24 hours(4). The BCF value for monolinuron in fish (golden orfe) and algae (Chlorella Fusca) were experimentally determined to be <20 (3-day at 45 ug/l) and 60 and 140 (24 hours at 50 ug/l), respectively(5). According to a recommended classification scheme(6), the experimental BCF values suggest that monolinuron should undergo moderate to high bioconcentration in aquatic organisms(SRC).

125.89 L/kg|The Koc for monolinuron has been estimated and experimentally determined to be 200(1,4). The Koc for monolinuron has also been experimentally determined to be 69.2(2). An average Koc value has been reported to be 40 in soils with organic carbon contents ranging from 0.58-2.3%(3). The Koc for monolinuron has been determined to be 60.3(5). The Koc values determined for monolinuron ranged from 211 to 2025 with an average of 517 in eight Czechoslovakian soils with organic matter contents ranging from 0.1-4.6%(6). The average Koc value for monolinuron in 10 different soils was determined to be 271.5(7). Another average Koc value has been determined to be 60(8). According to a recommended classification scheme(9), these Koc values suggest that monolinuron should have slight to very high mobility in soil(SRC).

The Henry's Law constant for monolinuron is estimated as 4.6X10-8 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 1.5X10-4 mm Hg(1), and water solubility, 930 mg/l(2). This value indicates that monolinuron will be essentially nonvolatile from water surfaces(3,SRC). Monolinuron's vapor pressure(1) and Henry's Law constant(1,2,SRC) indicate that volatilization from moist and dry soil surfaces should not occur(SRC).

SURFACE WATER: Monolinuron was qualitatively identified in river water (either British lowland river or a West German lowland river)(1). Monolinuron has been qualitatively detected in Dutch surface water resources(2).

Monolinuron was detected in one out of 26 sample of carrots at a concentration of 0.03 mg/kg(1).

Drug Information

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG; BETWEEN 1 OZ & 1 PT (OR 1 LB) FOR 70 KG PERSON (150 LB). /LINURON/

WHEN (14)C-LABELED MONOLINURON WAS FED TO HENS AT 0.25 & 25 MG/KG, 85-87% OF RADIOACTIVITY WAS EXCRETED IN URINE & FECES WITHIN 96 HR; MOST WAS IN URINE. THE ORGANS, INCLUDING BLOOD & BILE, CONTAINED APPROX 1% OF DOSE, & MUSCLE WAS ALMOST RESIDUE-FREE. EGG WHITES CONTAINED 0.31 & 0.53% AFTER 0.25 & 25 MG/KG; EGG YOLKS CONTAINED 1.82 & 3.72%. NO UNCHANGED MONOLINURON WAS FOUND IN FECES & URINE.|Absorbed by leaves & roots.|PENETRATES INTO WEEDS MAINLY THROUGH ROOTS BEING TRANSLOCATED IN PLANTS PREDOMINANTLY ACROPETAL.

WHEN...FED TO ALBINO RATS, THE FOLLOWING METABOLITES WERE FOUND...FREE & BOUND AS GLUCURONIDES OR SULFATES: N-(2-HYDROXY-4-CHLOROPHENYL)-N'-METHYLUREA; N-(3-HYDROXY-4-CHLOROPHENYL)-UREA; TRACES OF N-(4-CHLOROPHENYL)-N'-METHOXYUREA, 2-AMINO-5-CHLOROPHENOL, 2-ACETAMINO-5-CHLOROPHENOL, N,N'-BIS-(4-CHLOROPHENYL)UREA, 2-ACETAMINO-6-CHLOROPHENOL, & N-(2-HYDROXY-4-CHLOROPHENYL)-N'-METHYL-N'-METHOXYUREA. N-(4-CHLOROPHENYL)UREA & TRACE OF 4-CHLOROANILINE WERE FOUND FREE ONLY. N-(2-HYDROXY-4-CHLOROPHENYL)-N'-METHYLUREA WAS FOUND IN BOUND STATE ONLY.|WHEN (14)C-LABELED MONOLINURON WAS FED TO HENS AT 0.25 & 25 MG/KG, 26% OF EXCRETED RADIOACTIVITY WAS PRESENT AS METABOLITE 4-CHLOROPHENYLUREA. 1-(2-HYDROXY-4-CHLOROPHENYL)UREA AND 1-(3-HYDROXY-4-CHLOROPHENYL)UREA ACCOUNTED FOR 21% OF EXCRETED RADIOACTIVITY.|In...plants, cleavage of the methyl & methoxy groups on the terminal nitrogen atom, simultaneous ring hydroxylation & formation of 3-(2-hydroxy-4-chlorophenyl)urea & the corresponding 3-hydroxy compound. Further degradation is presumably by way of formation of the aniline derivative & ring splitting.|Six hours after administration of monolinuron to pigs, collected urine was analyzed. The biotransformation products found included 3-(4-chlorophenyl)-1-hydroxymethyl-1-methoxyurea, desmethyl monolinuron, 4-chlorophenylurea, (4-chloro-2-hydroxyphenyl)urea, (4-chloro-3-hydroxyphenyl)urea, and glucuronides and/or sulfates of the latter two hydroxy compounds.|For more Metabolism/Metabolites (Complete) data for MONOLINURON (8 total), please visit the HSDB record page.

Fresh air, rest.


Rinse skin with plenty of water or shower.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

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/

A 63 year old female drank 1 cup of Gramonol, containing monolinuron 14% and paraquat 10%. Nine hours post ingestion the patient was noted to have a cyanotic appearance. At 43 hours post ingestion she had a 36% methemoglobin level and a 7% sulfhemoglobin level. Hemolysis was also noted. The patient recovered after treatment with 50 mg of methylene blue. the patient's paraquat level was not in the serious risk category, and the patient's methemoglobinemia was attributed to monolinuron, which is metabolized to aniline.

3-(4-chlorophenyl)-1-methoxy-1-methylurea

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

Monolinuron Use and Manufacturing

Methods of Manufacturing

REACTION OF 4-CHLOROPHENYL ISOCYANATE WITH (N-METHYL) HYDROXYLAMINE, FOLLOWED BY REACTION WITH DIMETHYL SULFATE|Reaction of N,O-dimethylhydroxylamine with p-chlorophenyl isocyanate (isocyanate addition).

Uses

Used to control weeds in cereals and corn fields

Production

(1977) NOT PRODUCED COMMERCIALLY IN US|(1979) NOT PRODUCED COMMERCIALLY IN US

ARESIN 50, A WETTABLE POWDER /WITH/ 50% ACTIVE INGREDIENT; EMULSIFIABLE CONCENTRATE, 2 LB AI/IMPERIAL GAL; EMULSIFIABLE CONCENTRATE, 2 LB ACTIVE MONOLINURON PLUS 4 LB 2,4-D (ISO-OCTYL ESTER)/IMPERIAL GAL; EMULSIFIABLE CONCENTRATE, 2 LB ACTIVE MONOLINURON PLUS 4 LB MCPA (MIXED BUTYL ESTER)/IMPERIAL GAL; EMULSIFIABLE CONCENTRATE, 1 LB ACTIVE MONOLINURON PLUS 2 LB DINOSEB (AS AMINE)/IMPERIAL GALLON. MONOLINURON 25% + LINURON 25% WP; MONOLINURON 12% + DINOSEB ACETATE 35% WP.|...COLLOIDAL SUSPENSION WITH PARAQUAT...

Urea, N'-(4-chlorophenyl)-N-methoxy-N-methyl-: INACTIVE|SELECTIVE HERBICIDE FOR CONTROL OF BROAD LEAF WEEDS & ANNUAL GRASSES. ... MOST IMPORTANT FIELDS OF APPLICATION: ASPARAGUS, BEANS, ORCHARDS, ORNAMENTALS, ORNAMENTAL SHRUBS, POTATOES, VINEYARDS, WHEAT.

THE SUBSTITUTED PHENYLUREA HERBICIDES (INCL MONOLINURON) WERE EXTRACTED FROM GRAIN & SOIL SAMPLES WITH METHANOL & FROM AQUEOUS SAMPLES WITH METHYLENE CHLORIDE & SEPARATED BY HIGH PRESSURE LIQUID CHROMATOGRAPHY ON A SILANIZED SIO2 COLUMN USING METHANOL:WATER:AMMONIUM HYDROXIDE MOBILE PHASE. DETECTION LIMITS WERE 0.2 PPM FOR WHEAT & SOIL, & 0.01 PPM FOR WATER.|Analysis of residues: Alkaline hydrolysis, steam distillation, extraction of the resulting p-chloroaniline, back-titration with acid, diazotization, coupling with N-(1-naphthyl)ethylenediamine dihydrochloride, chromatographic clean-up, and elution of the dye. Determination by colorimetry at 560 nm.|FDA Method 242.1 "Organonitrogen Residues General Methods for Nonfatty Foods Including Acetone Extraction and Isolation in Organic Phase". Gas chromatography with electron capture detection. No detection limit reported.|FDA Method 242.4 "Method for Substituted Urea Herbicides". High Performance Liquid Chromatography with Fluorescence Detection. No detection limit reported.|For more Analytic Laboratory Methods (Complete) data for MONOLINURON (6 total), please visit the HSDB record page.

Agrochemicals -> Herbicides|Pharmaceuticals

Computed Properties

Molecular Weight:214.65
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:214.0509053
Monoisotopic Mass:214.0509053
Topological Polar Surface Area:41.6
Heavy Atom Count:14
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.