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CAS: 330-54-1
EINECS: 206-354-4
Molecular Formula: C9H10Cl2N2O
Molecular Weight: 233.09 g/mol
IUPAC Name: 3-(3,4-dichlorophenyl)-1,1-dimethylurea
DESCRIPTION:
DCMU (3-(3,4-dichlorophenyl)-1,1-dimethylurea) is an algicide and herbicide of the arylurea class that inhibits photosynthesis.
DCMU was introduced by Bayer in 1954 under the trade name of Diuron.
Diuron is a white crystalline solid.
Diuron 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.
Diuron is used as a herbicide.
Diuron is a member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which both of the hydrogens attached to one nitrogen are substituted by methyl groups, and one of the hydrogens attached to the other nitrogen is substituted by a 3,4-dichlorophenyl group.
Diuron has a role as a herbicide, a photosystem-II inhibitor, a xenobiotic, an environmental contaminant and a mitochondrial respiratory-chain inhibitor.
Diuron is a dichlorobenzene and a 3-(3,4-substituted-phenyl)-1,1-dimethylurea.
Diuron is used as an herbicide for weed control on noncrop lands and agricultural crops such as asparagus, pineapple, cotton, and sugarcane.
Diuron is also used as a sterilant in soil, a mildewcide in paints and stains, and an algicide in fish production.
A member of the class of ureas that is urea in which both of the hydrogens attached to one nitrogen are substituted by methyl groups, and one of the hydrogens attached to the other nitrogen is substituted by a 3,4-dichlorophenyl group.
Diuron is a white crystalline solid/wettable powder and used as a herbicide.
Diuron is registered for pre- and post-emergent herbicide treatment of both crop and non-crop areas, as a mildewcide and preservative in paints and stains, and as an algaecide.
Diuron is a substituted urea herbicide for the control of a wide variety of annual and perennial broad-leaved and grassy weeds on both crop and non-crop sites.
Thus, the application of diuron is wide for vegetation control and weed control in citrus orchards and alfalfa fields.
The mechanism of herbicidal action is the inhibition of photosynthesis.
Diuron was first registered in 1967.
Products containing diuron are intended for both occupational and residential uses.
Occupational uses include agricultural food and non-food crops; ornamental trees, flowers, and shrubs; paints and coatings; ornamental fish ponds and catfish production; and rights-of-way and industrial sites.
Residential uses include ponds, aquariums, and paints.
CAS: 330-54-1
EINECS: 206-354-4
Molecular Formula: C9H10Cl2N2O
Molecular Weight: 233.09 g/mol
IUPAC Name: 3-(3,4-dichlorophenyl)-1,1-dimethylurea
History of Diuron:
In 1952, chemists at E. I. du Pont de Nemours and Company patented a series of aryl urea derivatives as herbicides.
Several compounds covered by this patent were commercialized as herbicides: monuron (4-chlorophenyl), chlortoluron (3-chloro-4-methylphenyl) and DCMU, the (3,4-dichlorophenyl) example.
Subsequently, over thirty related urea analogs with the same mechanism of action reached the market worldwide.
Preparation Method of DIURON:
After mixing with appropriate amount of catalyst anhydrous FeCl3, 3,4-chloronitrobenzene was prepared by chlorine gas chlorination reaction at a certain temperature.
The nitro compound was reduced to give 3,4-= chloroaniline.
The resulting 3,4-= chloroaniline is added dropwise to a solution of toluene saturated with phosgene and reacted to give 3,4-= phenyl chloroisocyanate.
Finally, 3,4-= phenyl chloroisocyanate is reacted with dimethylamine to give trichloron.
Synthesis of Diuron:
As described in the du Pont patent, the starting material is a substituted aryl amine, an aniline, which is treated with phosgene to form its isocyanate derivative.
This is subsequently reacted with dimethylamine to give the final product.
Aryl-NH2 + COCl2 → Aryl-NCO
Aryl-NCO + NH(CH3)2 → Aryl-NHCON(CH3)2
Mechanism of action:
DCMU is a very specific and sensitive inhibitor of photosynthesis.
Diuron blocks the QB plastoquinone binding site of photosystem II, disallowing the electron flow from photosystem II to plastoquinone.
This interrupts the photosynthetic electron transport chain in photosynthesis and thus reduces the ability of the plant to turn light energy into chemical energy (ATP and reductant potential).
DCMU only blocks electron flow from photosystem II, Diuron has no effect on photosystem I or other reactions in photosynthesis, such as light absorption or carbon fixation in the Calvin cycle.
However, because Diuron blocks electrons produced from water oxidation in PS II from entering the plastoquinone pool, "linear" photosynthesis is effectively shut down, as there are no available electrons to exit the photosynthetic electron flow cycle for reduction of NADP+ to NADPH.
In fact, it was found that DCMU not only does not inhibit the cyclic photosynthetic pathway, but, under certain circumstances, actually stimulates it.
Because of these effects, DCMU is often used to study energy flow in photosynthesis.
CAS: 330-54-1
EINECS: 206-354-4
Molecular Formula: C9H10Cl2N2O
Molecular Weight: 233.09 g/mol
IUPAC Name: 3-(3,4-dichlorophenyl)-1,1-dimethylurea
Chemical and Physical Properties of DIURON:
Melting point: 158-159°C
Boiling point : 180-190°C
Density: 1.48
vapor pressure: 2(x 10-7 mmHg) at 30 °C
refractive index : 1.5500 (estimate)
Fp : 180-190°C
storage temp:. 2-8°C
solubility In acetone: 5.3 wt % at 27 °C (Meister, 1988).
form : neat
pka: -1 to -2 (quoted, Bailey and White, 1965)
color : White, odorless crystalline solid
Water Solubility : Slightly soluble. 0.0042 g/100 mL
Merck: 14,3382
BRN : 2215168
Henry's Law Constant: 1.46(x 10-9 atm?m3/mol) at 25 °C (approximate - calculated from water solubility and vapor pressure)
Exposure limits NIOSH REL: TWA 10 mg/m3.
Stability: Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
Molecular Weight: 233.09
XLogP3: 2.7
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 1
Exact Mass: 232.0170183
Monoisotopic Mass: 232.0170183
Topological Polar Surface Area: 32.3 Ų
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
Compound Is Canonicalized: Yes
Color/Form: White, crystalline solid
Odor: Odorless
Decomposition:
Hazardous decomposition products formed under fire conditions: Carbon oxides, nitrogen oxides (NOx), hydrogen chloride gas.
Corrosivity: Non-corrosive
CAS: 330-54-1
EINECS: 206-354-4
Molecular Formula: C9H10Cl2N2O
Molecular Weight: 233.09 g/mol
IUPAC Name: 3-(3,4-dichlorophenyl)-1,1-dimethylurea
Usage And Synthesis of DUIRON:
DIURON is used as pre-emergent herbicide.
DIURON is used as A phenyl urea herbicide.
Diuron is a urea compound used as a preemergence herbicide in soils to control germinating broad-leaved grasses and weeds in crops such as apples, cotton, grapes, pears, pineapple and alfalfa; sugar cane lowering depressant.
Air & Water Reactions: Very slightly soluble in water.
Reactivity Profile: Diuron is incompatible with the following: Strong acids .
Agricultural Uses:
Herbicide: Diuron is a substituted urea herbicide used to control a wide variety of annual and perennial broadleaf and grassy weeds, as well as mosses.
Diuron is used on non-crop areas and many agricultural crops such as fruit, cotton, sugar cane, alfalfa, and wheat.
Diuron works by inhibiting photosynthesis.
Diuron may be found in formulations as wettable powders and suspension concentrates.
Diuron is substituted urea herbicides, with the role of absorption conduction and a certain Contact killing effect.
At low doses, the herbicide can be selected by the difference and the time difference.
At high doses, Diuron becomes a killing herbicide.
Diuron is mainly used for cotton, soybean, tomato, tobacco, strawberry, grape, Orchard, rubber plantation and other crops to control the annual grass weeds such as drought, Horse Tang, green grass, wild amaranth, cyperus, etc.
CAS: 330-54-1
EINECS: 206-354-4
Molecular Formula: C9H10Cl2N2O
Molecular Weight: 233.09 g/mol
IUPAC Name: 3-(3,4-dichlorophenyl)-1,1-dimethylurea
Safety Profile:
Questionable carcinogen with experimental tumorigenic and teratogenic data.
Mutation data reported.
When heated to decomposition it emits highly toxic fumes of Cland NOx.
Environmental Fate: Biological.
Degradation of radiolabeled diuron (20 ppm) was not observed after 2 weeks of culturing with Fusarium and two unidentified microorganisms.
After 80 days, only 3.5% of the applied amount evolved as 14CO2.
In 8 weeks, <20% of diuron in soil (60 ppm) was detoxified.
3,4-Dichloroaniline was reported as a minor degradation product of diuron in water and soils.
Under aerobic conditions, mixed cultures isolated from pond water and sediment degraded diuron (10 μg/mL) to CPDU, 3,4-dichloroaniline, 3-(3,4-dichlorophenyl)-1methylurea, carbon dioxide and a monodemethylated product.
The extent of biodegradation varied with time, glycerol concentration and microbial population.
The degradation half life was <70 days at 30°C.
Thom and Agg (1975) reported that diuron is amenable to biological treatment with acclimation.
Soil. Several degradation pathways were reported. The major products and reaction pathways include formation of 1-methyl-3-(3,4-dichlorophenol) ur
Incubation of diuron in soils releases carbon dioxide.
The rate of carbon dioxide formation nearly tripled when the soil temperature was increased from 25 to 35°C.
Reported half-lives in an Adkins loamy sand are 705, 414 and 225 d
The half-lives for diuron in field soils ranged from 133 to 212 days with an average half-life of 328 days.
The degradation of diuron using a Cecil loamy sand (1 ppm) and Brookstone silty clay loam (5 ppm) in the laboratory maintained at 27°C and 60% relative humidity.
In both soils, diuron was applied on four separate occasions over 22 weeks.
In both instances, the investigators observed 40% of the applied amount degraded in both soils.
In a field application study, diuron did not leach below 5 cm in depth despite repeated applications or water addition
Diuron has a high potential to leach to groundwater.
CAS: 330-54-1
EINECS: 206-354-4
Molecular Formula: C9H10Cl2N2O
Molecular Weight: 233.09 g/mol
IUPAC Name: 3-(3,4-dichlorophenyl)-1,1-dimethylurea
SAFETY INFORMATION ABOUT DIURON:
Hazards:
Reactivity Alerts
none
Air & Water Reactions:
Very slightly soluble in water.
Fire Hazard:
Special Hazards of Combustion Products: Highly toxic fumes are imminent
Behavior in Fire: Decomposes at 180° to 190°C
Health Hazard:
INHALATION: May cause irritation of nose and throat.
EYES: Irritation.
SKIN: Moderately irritating to skin.
Reactivity Profile:
DIURON is incompatible with the following: Strong acids
Belongs to the Following Reactive Group(s)
Amides and Imides
Aryl Halides
Isolation and Evacuation:
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 the immediate precautionary measure distance, in the downwind direction, as necessary.
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.
Firefighting:
SMALL FIRE: Dry chemical, CO2, water spray or regular foam.
LARGE FIRE:
Water spray, fog or regular foam.
Do not scatter spilled material with high-pressure water streams.
If it can be done safely, move undamaged containers away from the area around the fire.
Dike runoff from fire control for later disposal.
FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire.
Non-Fire Response:
Do not touch or walk through spilled material.
Stop leak if you can do it without risk.
Prevent dust cloud. For Asbestos, avoid inhalation of dust.
Cover spill with plastic sheet or tarp to minimize spreading.
Do not clean up or dispose of, except under supervision of a specialist.
SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area.
SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal.
LARGE SPILL: Dike far ahead of liquid spill for later disposal.
Cover powder spill with plastic sheet or tarp to minimize spreading.
Prevent entry into waterways, sewers, basements or confined areas.
Protective Clothing:
Skin: PREVENT SKIN CONTACT - Wear appropriate personal protective clothing to prevent skin contact.
Eyes: PREVENT EYE CONTACT - Wear appropriate eye protection to prevent eye contact.
Wash skin: DAILY - The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc.
Remove: No recommendation is made specifying the need for removing clothing that becomes wet or contaminated.
Change: DAILY - Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
First Aid
Eye: IRRIGATE IMMEDIATELY
If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids.
Get medical attention immediately.
Skin: WATER FLUSH IMMEDIATELY
If this chemical contacts the skin, immediately flush the contaminated skin with water.
If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water.
Get medical attention promptly.
Breathing: RESPIRATORY SUPPORT
If a person breathes large amounts of this chemical, move the exposed person to fresh air at once.
If breathing has stopped, perform artificial respiration.
Keep the affected person warm and at rest.
Get medical attention as soon as possible.
Swallow: MEDICAL ATTENTION IMMEDIATELY
If this chemical has been swallowed, get medical attention immediately.
HANDLING AND STORAGE:
PROCEDURE FOR HANDLING
• Avoid all personal contact, including inhalation.
• Wear protective clothing when risk of exposure occurs.
Empty containers may contain residual dust which has the potential to accumulate following settling. Such dusts may explode in the presence of an appropriate ignition source.
• Do NOT cut, drill, grind or weld such containers.
• In addition ensure such activity is not performed near full, partially empty or empty containers without appropriate workplace safety authorisation or permit.
RECOMMENDED STORAGE METHODS:
• Polyethylene or polypropylene container.
• Check all containers are clearly labelled and free from leaks.
STORAGE REQUIREMENTS:
Observe manufacturer's storing and handling recommendations.
CAS: 330-54-1
EINECS: 206-354-4
Molecular Formula: C9H10Cl2N2O
Molecular Weight: 233.09 g/mol
IUPAC Name: 3-(3,4-dichlorophenyl)-1,1-dimethylurea
Synonyms:
MeSH Entry Terms:
3-(3,4-Dichlorophenyl)-1,1-dimethylurea
DCMU
Diuron
Depositor-Supplied Synonyms:
diuron
330-54-1
3-(3,4-Dichlorophenyl)-1,1-dimethylurea
DCMU
Duran
Dynex
Dichlorfenidim
Herbatox
Vonduron
Dailon
Karmex
Marmer
Karmex DW
Di-on
Cekiuron
Crisuron
Lucenit
Unidron
1,1-Dimethyl-3-(3,4-dichlorophenyl)urea
Diuron Nortox
Karmex D
Karmex Diuron Herbicide
1-(3,4-Dichlorophenyl)-3,3-dimethylurea
Preventol A 6
Urox D
Diuron 4L
Direx 4L
DP Hardener 95
Telvar Diuron Weed Killer
Urea, N'-(3,4-dichlorophenyl)-N,N-dimethyl-
N'-(3,4-Dichlorophenyl)-N,N-dimethylurea
N-(3,4-Dichlorophenyl)-N',N'-dimethylurea
DCMU 99
HW 920
Karamex
UNII-9I3SDS92WY
N,N,-Dimethyl-N'-(3,4-dichlorophenyl)urea
Urea, 3-(3,4-dichlorophenyl)-1,1-dimethyl-
3-(3,4-Dichlor-phenyl)-1,1-dimethyl-harnstoff
1-(3,4-Dichlorophenyl)-3,3-dimethyluree
CHEBI:116509
9I3SDS92WY
3-(3,4-dichlorophenyl)-1,1-dimethyl-urea
3-(3,4-Dicloro-fenyl)-1,1-dimetil-urea
3-(3,4-Dichloor-fenyl)-1,1-dimethylureum
DTXSID0020446
MFCD00018136
NCGC00094525-01
Anduron
Ansaron
Dirurol
Durashield
Herburon
Seduron
Bioron
Drexel
Farmco diuron
DSSTox_CID_446
3-(3,4-Dichloro-phenyl)-1,1-dimethyl-urea
Sup'r flo
DSSTox_RID_75595
DSSTox_GSID_20446
Diuron 900
Caswell No. 410
Ditox-800
Aguron
Diater
Diuron solution
Dichlorfenidim [Russian]
USAF P-7
Diuron [ANSI:BSI:ISO]
USAF XR-42
CAS-330-54-1
CCRIS 1012
HSDB 382
Direx 80W
NSC 8950
EINECS 206-354-4
AF 101
EPA Pesticide Chemical Code 035505
BRN 2215168
Xarmex
N-(3,4-Dichlorophenyl)-N,N-Dimethylurea
AI3-61438
Karmex DL
1-(3,4-Dichlorophenyl)-3,3-dimethyluree [French]
3-(3,4-Dichloor-fenyl)-1,1-dimethylureum [Dutch]
3-(3,4-Dicloro-fenyl)-1,1-dimetil-urea [Italian]
Karmex 80W
3-(3,4-Dichlor-phenyl)-1,1-dimethyl-harnstoff [German]
Spectrum_001823
1-(3,3-dimethylurea
3-(3,1-dimethylurea
SpecPlus_000424
N'-(3,N-dimethylurea
N-(3,N'-dimethylurea
1,4-dichlorophenyl)urea
3-(3,1-dimethylureum
n,n-dimethyl-n'-(3,4-dichlorophenyl)urea
3-(3,1-dimetil-urea
Spectrum2_001229
Spectrum3_000822
Spectrum4_000662
Spectrum5_001956
Diuron, >=98%
EC 206-354-4
Cambridge id 5104305
SCHEMBL7279
3-(3,1-dimethyl-harnstoff
BSPBio_002343
KBioGR_001063
KBioSS_002328
SPECTRUM330030
MLS002207110
DivK1c_006520
SPBio_001078
CHEMBL278489
KBio1_001464
KBio2_002325
KBio2_004893
KBio2_007461
KBio3_001843
ZINC57287
NSC8950
WLN: GR BG DMVN1 & 1
HY-B0860
NSC-8950
Tox21_111292
Tox21_201438
Tox21_301016
BDBM50487027
CCG-39151
Diuron 10 microg/mL in Acetonitrile
STK077954
AKOS001303464
Diuron 100 microg/mL in Acetonitrile
Tox21_111292_1
Urea,4-dichlorophenyl)-N,N-dimethyl-
MCULE-1921281405
Urea,4-dichlorophenyl)-1,1-dimethyl-
NCGC00094525-02
NCGC00094525-03
NCGC00094525-04
NCGC00094525-05
NCGC00094525-06
NCGC00094525-07
NCGC00094525-08
NCGC00094525-09
NCGC00254918-01
NCGC00258989-01
AS-15493
P597
SMR000777941
Diuron, PESTANAL(R), analytical standard
3-(3,4-Dichlorophenol)-1,1-dimethylurea
DB-048327
Diuron solution 100 ng/muL in acetonitrile
CS-0012874
D1328
FT-0603378
FT-0667750
N,N-dimethyl-N'-(3,4-dichlorophenyl)-urea
N-(3,4-dichlorophenyl)-N',N'-dimethyl urea
C18428
A821585
Q425389
SR-01000195223
Diuron, certified reference material, TraceCERT(R)
J-018992
SR-01000195223-1
BRD-K75330923-001-02-6
Diuron solution, 100 mug/mL in acetonitrile, PESTANAL(R), analytical standard
W9M
