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Diuron(CAS No. 330-54-1)

Diuron C9H10Cl2N2O (cas 330-54-1) Molecular Structure

330-54-1 Structure

Identification and Related Records

【Name】
Diuron
【CAS Registry number】
330-54-1
【Synonyms】
Urea,N'-(3,4-dichlorophenyl)-N,N-dimethyl-
Herbatox
3-(3,4-dichlorophenyl)-1,1-dimethyl-urea
3-(3,4-Dichlorophenyl)-1,1-dimethylurea
Urea, 3- (3,4-dichlorophenyl)-1,1-dimethyl-
DP Hardener 95
HW 920
Karamex
DIMETHOMORPH
Vonduron
1-(3,4-Dichlorophenyl)-3,3-dimethylurea
Urea, N- (3,4-dichlorophenyl)-N,N-dimethyl-
DCMU
DCMU 99
Karmex D
N-(3,4-Dichlorophenyl)-N, N-dimethylurea
Dailon
Dyhard UR 200
3- (3,4-Dichloor-fenyl)-1, 1-dimethylureum(DUTCH)
Karmex DW
Dynex
Dichlorfenidim
Karmex Diuron Herbicide
Di-On
3-(3,4-Dichlorophenol)-1, 1-dimethylurea
N-(3,4-Dichlorophenyl)-N,N-dimethylurea
Diurex
1, 1-Dimethyl-3-(3,4-dichlorophenyl)urea
Marmer
Duran
3- (3, 4-Dicloro-fenyl)-1,1-dimetil-urea(Italian)
Lucenit
Karmex
Telvar Diuron Weed Killer
3- (3,4-Dichlor-phenyl)-1, 1-dimethyl-harnstoff(GERMAN)
DMU
Diuron Tech (3-(3,4-Dichlorophenyl)-1,1-Dimethylurea)
3-(3,4-DICLORO-FENYL)-1,1-DIMETIL-UREA (ITALIAN)
CEKIURON
3-(3,4-DICHLOR-PHENYL)-1,1-DIMETHYL-HARNSTOFF (GERMAN)
3-(3,4-DICHLOOR-FENYL)-1,1-DIMETHYLUREUM (DUTCH)
TELVAR
N′-(3,4-DICHLOROPHENYL)-N,N-DIMETHYLUREA
DIATER
DIUROL
FARMCO DIURON
1-(3,4-DICHLOROPHENYL)-3,3-DIMETHYLUREE (FRENCH)
3-(3,4-DICHLOROPHENOL)-1,1-DIMETHYLUREA
DIURON 4L
UNIDRON
DREXEL
AF 101
DREXEL DIURON 4L
1,1-DIMETHYL-3-(3,4-DICHLOROPHENYL)UREA
CRISURON
DIREX 4L
USAF XR-42
USAF P-7
N-(PHOSPHONOMETHYL)GLYCINE
Diuron 95%TC
Diuron 98%TC
Diuron 50%WP
80%WDG
【EINECS(EC#)】
206-354-4
【Molecular Formula】
C9H10Cl2N2O (Products with the same molecular formula)
【Molecular Weight】
233.095
【Inchi】
InChI=1S/C9H10Cl2N2O/c1-13(2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)
【InChIKey】
XMTQQYYKAHVGBJ-UHFFFAOYSA-N
【Canonical SMILES】
CN(C)C(=O)NC1=CC(=C(C=C1)Cl)Cl
【MOL File】
330-54-1.mol

Chemical and Physical Properties

【Appearance】
white crystalline solid
【Density】
1.369 g/cm3
【Melting Point】
158-159℃
【Boiling Point】
385.2 °C at 760 mmHg
【Refractive Index】
1.605
【Flash Point】
186.7 °C
【Water】
Slightly soluble. 0.0042 g/100 mL
【Solubilities】
0.0042 g/100 mL in water
【Color/Form】
White, crystalline solid
【Stability】
Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
【Storage temp】
APPROX 4°C
【Spectral properties】
Intense mass spectral peaks: 72 m/z (100%), 232 m/z (38%), 234 m/z (26%), 44 m/z (26%)
Intense mass spectral peaks: 59 m/z, 124 m/z, 174 m/z, 187 m/z, 219 m/z
【Computed Properties】
Molecular Weight:233.0945 [g/mol]
Molecular Formula:C9H10Cl2N2O
XLogP3:2.7
H-Bond Donor:1
H-Bond Acceptor:1
Rotatable Bond Count:1
Tautomer Count:2
Exact Mass:232.017018
MonoIsotopic Mass:232.017018
Topological Polar Surface Area:32.3
Heavy Atom Count:14
Formal Charge:0
Complexity:211
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 Ring Count:1
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:10

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22;R40;R48/22;R50/53
【Safety Statements 】
S2;S13;S22;S23;S37;S46;S60;S61;S61
【HazardClass】
9
【Safety】

Hazard Codes:?HarmfulXn,?DangerousN,?FlammableF
Risk Statements: 22-40-48/22-50/53-36-20/21/22-11?
R22:Harmful if swallowed.?
R40:Limited evidence of a carcinogenic effect.?
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R36:Irritating to eyes.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R11:Highly flammable.
Safety Statements: 13-22-23-37-46-60-61-2-36/37-26?
S13:Keep away from food, drink and animal foodstuffs.?
S22:Do not breathe dust.?
S23:Do not breathe vapour.?
S37:Wear suitable gloves.?
S46:If swallowed, seek medical advice immediately and show this container or label.
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S2:Keep out of the reach of children.?
S36/37:Wear suitable protective clothing and gloves.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: YS8925000
HazardClass: 9
PackingGroup: III

【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
MAY IRRITATE EYES, NOSE, THROAT, & SKIN.
【Cleanup Methods】
Spills of pesticides at any stage of their storage or handling should be treated with great care. Liquid formulations may be reduced to solid phase by evaporation. Dry sweeping of solids is always hazardous: These should be removed by vacuum cleaning or by dissolving them in water or other solvent in the factory environment. In the field they may be washed away with water into a suitable soak-hole. /Pesticides/
CLEANING GLASSWARE & SPRAY EQUIPMENT: FLUSH TANK, PUMP, HOSES, & BOOM WITH SEVERAL CHANGES OF WATER AFTER REMOVING NOZZLE TIPS & SCREENS (CLEAN THESE PARTS SEPARATELY). GLASSWARE CAN BE CLEANED BY THOROUGH WASHING WITH DETERGENT FOLLOWED BY ACETONE RINSE.
Hydrolysis is not recomended as a /cleanup/ procedure because of the generation of the toxic products, 3,4-dichloroaniline and dimethylamine.
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.
Environmental considerations: Water spill: If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
【Transport】
UN 2767
【Fire Fighting Procedures】
If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.)
【Fire Potential】
Not flammable
【Formulations/Preparations】
USEPA/OPP Pesticide Code 035505; Trade Names: Karmex; Cekiuron; Crisuron; Dailon; Diater; DI-ON; Direx 4L; Diurex; Diurol; Vonduron; Drexel diuron 4L; Dynex; Krovar, Ureabor, Unidron.
Formulation types: wettable powder, suspension concentrate
Formulations: Flowable, granule, wettable powder
GRADES: TECHNICAL MATERIAL, 95%, WETTABLE POWDER, 80%.
【Reactivities and Incompatibilities】
... COMPATIBLE WITH MOST OTHER HERBICIDES WITH WHICH THEY MIGHT BE MIXED. CERTAIN ESTER FORMULATIONS OF HORMONE WEED KILLERS MAY CREATE A PHYSICAL PROBLEM IN SPRAY TANK. /DIURON FORMULATIONS/
Treatment at elevated temperatures by acid or base yields dimethylamine and 3,4-dichloroaniline.
Strong acids.
【Other Preventative Measures】
AVOID BREATHING DUST OR SPRAY MIST. AVOID CONTACT WITH SKIN, EYES, & CLOTHING. KEEP OUT OF REACH OF CHILDREN.
Smoking, eating, drinking /and the use of toilet facilities/ before washing should be absolutely prohibited when any pesticide of moderate or higher toxicity is being handled or used. /Pesticides/
Handling and storage cautions. ... Avoid nose, skin contact or breathing dust, spary mist. Wash contaminated clothing with soap, hot water before re-use.
If material not involved in fire: Keep material out of of water sources and sewers. Build dikes to contain flow as necessary.
Personnel protection: Keep upwind. ... Avoid breathing vapors or dusts. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
The worker should wash daily at the end of each work shift.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
【Protective Equipment and Clothing】
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
【Specification】

?Diuron (CAS NO.330-54-1) is also named as 1,1-Dimethyl-3-(3,4-dichlorophenyl)urea ; 1-(3,4-Dichlorophenyl)-3,3-dimethylurea ; 1-(3,4-Dichlorophenyl)-3,3-dimethyluree ; 1-(3,4-Dichlorophenyl)-3,3-dimethyluree [French] ; 3-(3,4-Dichlorophenyl)-1,1-dimethylurea ; 3-(3,4-Dicloro-fenyl)-1,1-dimetil-urea ; 3-(3,4-Dicloro-fenyl)-1,1-dimetil-urea [Italian] ; 4-12-00-01263 (Beilstein Handbook Reference) ; AF 101 ; AI3-61438 ; Anduron ; Ansaron ; BRN 2215168 ; Bioron ; CCRIS 1012 ; Caswell No. 410 ; Cekiuron ; Crisuron ; DCMU ; DCMU 99 ; Dirurol ; Ditox-800 ; Duran ; Durashield ; Dynex ; EPA Pesticide Chemical Code 035505 ; Farmco diuron ; HSDB 382 ; HW 920 ; Herbatox ; Herburon ; N'-(3,4-Dichlorophenyl)-N,N-dimethylurea ; N,N,-Dimethyl-N'-(3,4-dichlorophenyl)urea ; N-(3,4-Dichlorophenyl)-N',N'-dimethylurea ; NSC 8950 ; Preventol A 6 ; Seduron ; Sup'r flo ; Telvar diuron weed killer ; USAF P-7 ; USAF XR-42 ; Unidron ; Urox D ; Vonduron .?Diuron (CAS NO.330-54-1) is?a white crystalline solid.?It is a wettable powder. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Diuron can cause illness by inhalation, skin absorption and/or ingestion. It is very slightly soluble in water. Diuron is incompatible with strong acids. It may cause irritation of nose and throat.

【Octanol/Water Partition Coefficient】
log Kow= 2.68
【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.
Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/
Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/
Water treatment method: Powdered activated carbon: Freundlich adsorption parameters: K: 0.095, 1/n= 0.109; Carbon dose to reduce 5 mg/l to a final concn of 0.1 mg/l: 66 mg/l, Carbon dose to reduce 1 mg/l to a final concn of 0.1 mg/l: 12 mg/l
Chemical and thermal decontamination of 20 pesticides, including diuron, dicamba and dalapon are described. Differential thermal analysis showed that complete incineration temperatures of the reagent grade pesticides ranged from about 250 deg C to approximately 850 deg C; 15 of the compounds were completely combustible at 700 deg C or below, while 5 required 700 to 900 deg C. Dalapon contained about 10% of uncombustible residue at 1000 deg C. [Kennedy MV et al; Residue Rev 29: 89-104 (1969)] PubMed Abstract
Diuron, stable under normal conditions, decomposes on heating to 180 to 190 deg C giving dimethylamine and 2,4-dichlorophenyl isocyanate. 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 products, 3,4-dichloroaniline and dimethylamine. Proper incineration may be the best method to dispose of diuron. Recommendable methods: Landfill & incineration. Not recommendable method: Hydrolysis. Peer review: Incinerate at high temp in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

PREPN: ... BY REACTION OF 3,4-DICHLOROPHENYL ISOCYANATE WITH DIMETHYLAMINE ... .
U.S. Imports

(1977) 4.15X10+7 G
(1982) 3.68X10+8 G
U.S. Production

(1981) 2.7X10+9 G (SALES)
Consumption Patterns

INDUSTRIAL COMMERCIAL USES-EG, ON RAILROAD RIGHTS-OF-WAY, 57%; COTTON, 19%; CITRUS CROPS, 12%; DECIDUOUS FRUITS & NUTS, 3%; WHEAT, 3%; VEGETABLES, 2%; OTHER FIELD CROPS, EG, ALFALFA & SUGARCANE, 4% (1978 HERBICIDE USE)
(1978) 2.63X10+9 G (CONSUMPTION)
The annual agricultural use of diuron as a herbicide in the United States was estimated as approximately 3.6X10+6 lbs for 1992.
【Usage】

Herbicide.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
【Biomedical Effects and Toxicity】
IN RATS & DOGS FED DIURON, EXCRETION OF METABOLITES OCCURRED IN BOTH FECES & URINE.
ROOT UPTAKE OF (14)C-DIURON FROM SOLN WAS STUDIED. ... SMALL AMT OF THE MONOMETHYL & DEMETHYLATED DERIVATIVES WERE FOUND IN NUTRIENT SOLN FROM ... SOYBEANS, ... OAT, & CORN TOPS.
DIURON IS MOST READILY ABSORBED THROUGH THE ROOT SYSTEM; LESS SO THROUGH FOLIAGE & STEMS. TRANSLOCATION IS PRIMARILY UPWARD IN XYLEM.
Diuron was fed to five dairy cows at 0-550 ppm concn levels. About 50% of the diuron was detected in the urine, 10% in the feces and 5% in the blood. Milk samples did not contain diuron. A positive correlation was noted between the concn of diuron products in urine and blood and a negative correlation between urine and feces. It is suggested that the remaining diuron is absorbed in the body or degraded into undetectable metabolites. [Kalra SK, Chahal KS; Ecotoxicol Environ Saf 3 (4): 362-8 (1979)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), a range of Koc values from 224-879(2-7), indicates that diuron is expected to have low-to-moderate mobility in soil(SRC). Volatilization of diuron from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 6.9X10-8 mm Hg(6), and water solubility, 36.4 mg/l(8). Diuron is not expected to volatilize from dry soil surfaces(SRC) based upon the vapor pressure(6). Diuron is a highly persistent and fairly immobile herbicide(9). When applied to soil it has a mean half-life of approximately 330 days and will not leach below 5 to 10 cm from the surface(9). Metabolites of microbial degradation include the major metabolite, 3,4-dichloroaniline, and also 3-(3,4-dichlorophenyl)urea and 3-(3,4-dichlorophenyl)-1-methylurea(9). The levels of diuron found in citrus groves in Florida in which it was used for 7-8 years ranged from 3.7 to 13.1% of the total diuron applied(10).
AQUATIC FATE: Based on a classification scheme(1), a range of experimental Koc values from 224-879(2-7), indicates that diuron is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(8) based upon an estimated Henry's Law constant of 5.8X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 6.9X10-8 mm Hg(6), and water solubility, 36.4 mg/l(9). Carp (Cyprinus carpio) exposed for 6 weeks to diuron had experimental BCF values ranging from 3.4-4.9 (0.5 mg/l exposure) and
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diuron, which has a vapor pressure of 6.9X10-8 mm Hg at 25 deg C(2), is expected to exist solely in the particulate phase in the ambient atmosphere(SRC). Particulate-phase diuron may be removed from the air by wet and dry deposition(SRC). Diuron absorbs light in the environmental spectrum(3), and has the potential for direct photolysis(SRC).

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