330-54-1

Basic information

• Product Name: Diuron
• Synonyms: Twinfilin 1;1-(3,4-dichlorophenyl)-3,3-dimethyluree;1-(3,4-dichlorophenyl)-3,3-dimethyluree(french);3-(3,4-Dichloor-fenyl)-1,1-dimethylureum;3-(3,4-Dichlorophenol)-1,1-dimethylurea;3-(3,4-dichlorophenyl)-1,1-dimethyl-ure;3-(3,4-Dichlorophenyl)-N,N-dimethylurea;3-(3,4-Dichlor-phenyl)-1,1-dimethyl-harnstoff
• CAS NO: 330-54-1
• Molecular Formula: C₉H₁₀Cl₂N₂O
• Molecular Weight: 233.09
• EINECS: 206-354-4
• Product Categories: Organics;ACTIVE AGROCHEMICAL INGREDIENTS;INSECTICIDE;2000/60/EC;Alpha sort;D;DAlphabetic;DIO - DIZMethod Specific;European Community: ISO and DIN;Pesticides&Metabolites;Agro-Products;Aromatics;Bioactive Small Molecules;Building Blocks;Carbonyl Compounds;Cell Biology;Chemical Synthesis;DIG-DY;Organic Building Blocks;Ureas;pesticide
• Mol File: 330-54-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: 158-159°C
• Boiling Point: 180-190°C
• Flash Point: 180-190°C
• Appearance: white crystalline solid
• Density: 1.48
• Vapor Pressure: 3.88E-06mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: APPROX 4°C
• Solubility: In acetone: 5.3 wt % at 27 °C (Meister, 1988).
• PKA: -1 to -2 (quoted, Bailey and White, 1965)
• Water Solubility: Slightly soluble. 0.0042 g/100 mL
• Stability: Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
• Merck: 14,3382
• BRN: 2215168
• CAS DataBase Reference: Diuron(CAS DataBase Reference)
• NIST Chemistry Reference: Diuron(330-54-1)
• EPA Substance Registry System: Diuron(330-54-1)

Safety Data

• Hazard Codes: Xn,N,F
• Statements: 22-40-48/22-50/53-36-20/21/22-11
• Safety Statements: 13-22-23-37-46-60-61-2-36/37-26-16
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: YS8925000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 330-54-1(Hazardous Substances Data)

Usage

Description

Diuron (330-54-1) is used as an herbicide for weed control on noncrop lands and agricultural crops such as asparagus, pineapple, cotton, and sugarcane. It is also used as a sterilant in soil, a mildewcide in paints and stains, and an algicide in fish production.

Chemical Properties

White, odorless crystalline solid

Uses

Different sources of media describe the Uses of 330-54-1 differently. You can refer to the following data:
1. Pre-emergent herbicide.
2. A phenyl urea herbicide. Pre-emergent herbicide.
3. 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 ?owering depressant.

Definition

ChEBI: 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.

General Description

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.

Air & Water Reactions

Very slightly soluble in water.

Reactivity Profile

Diuron is incompatible with the following: Strong acids .

Health Hazard

Different sources of media describe the Health Hazard of 330-54-1 differently. You can refer to the following data:
1. INHALATION: May cause irritation of nose and throat. EYES: Irritation. SKIN: Moderately irritating to skin.
2. Acute and chronic toxicity was found to be oflow order in experimental animals, administered by oral route; repeated doses producedanemia in rats; the LD50 data, however,reported in the literature significantly differ; moderately toxic by intraperitoneal route,while the inhalation risk is low because oflow vapor pressure. Susceptible to hydrolyzeto dichloroaniline in vivo, which can causemethemoglobinemia; no evidence of carcino-genicity in an 18-month study in mice at1400 ppm (Innes et al, 1969); no adverseeffect observed in rats in 2-year feeding studies at dietary concentration level of 250 ppm(ACGIH 1986); adverse reproductive effectsmay arise from chronic exposure to high con-centration level.LD50 oral (rat): 1017 mg/kg (Lewis 1995)LD50 oral (rat): 3400 mg/kg (Hodge et al1968)LD LO intraperitoneal (mouse): 500 mg/kg.

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. It is used on non-crop areas and many agricultural crops such as fruit, cotton, sugar cane, alfalfa, and wheat. Diuron works by inhibiting photosynthesis. It may be found in formulations as wettable powders and suspension concentrates.

Trade name

330541?; AF 101?; AI3-61438?; AMETRON SC?; BOUNDRY?[C]; CHEMIURON?[C]; CEKIURON?; CRISURON?; DAILON?; DIATER?; DI-ON?; DIREX?; DITOX?; DIUMATE? Diuron; DIUREX?,[C]; DIUROL? Diuron; DIURON 4L?; DMU?; DREXEL DIURON 4L?; DROPP ULTRA?; DURAN?; DYNEX?[C] FARMCO DIURON?; FORTEX SC?; FREEFLO?; GINSTAR?; HERBURON 500 BR?; HW 920?; KARMEX?[C]; K-4?; KARMEX DIURON HERBICIDE?; KARMEX DW?; KROVAR IDF?[C]; MARMER?; STRIKER?; SUP'R FLO?; TELVAR?; TIGREX?; TREVISSIMO?; UNIDRON?; UROX D?[C]; VONDURON?

Safety Profile

oneal routes. Questionable carcinogen with experimental tumorigenic and teratogenic data. Mutation data reported. When heated to decomposition it emits highly toxic fumes of Cland NOx. See also CHLOROPHENOLS.

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 (Lopez and Kirkwood, 1974). In 8 weeks, <20% of diuron in soil (60 ppm) was detoxified (Corbin and Upchurch, 1967). 3,4-Dichloroaniline was reported as a minor degradation product of diuron in water (Drinking Water Health Advisory, 1989) and soils (Duke et al., 1991). 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 halflife was <70 days at 30°C (Ellis and Camper, 1982).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) urIncubation of diuron in soils releases carbon dioxide (Madhun and Freed, 1987). 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 dThe half-lives for diuron in field soils ranged from 133 to 212 days with an average half-life of 328 days (Hill et al., 1955). Hill et al. (1955) studied 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 (Majka and Lavy, 1977). Groundwater. According to the U.S. EPA (1986) diuron has a high potential to leach to groundwater.

Purification Methods

Recrystallise it from 95% EtOH [Beck et al. J Am Chem Soc 108 4018 1986]. [Beilstein 12 IV 1263.]

Toxicity evaluation

Diuron is a selective inhibitor of the Hill reaction in plant photosynthesis. In some mammalian carcinogenic studies, repeated high-dose exposure to diuron appeared to work as a tumor promoter, and diuron may elicit tumor formation by inducing cytotoxicity with subsequent sustained cell proliferation.

InChI:InChI=1/C9H10Cl2N2O/c1-13(2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)

Upstream product

• 124-40-3 dimethyl amine 
• 102-36-3 3,4-dichlorophenylisocyanate 
• 7159-94-6 ethyl (3,4-dichlorophenyl)carbamate 
• 2327-02-8 3,4-dichlorophenylurea 
• 2150-28-9 isopropyl N-(3,4-dichlorophenyl)carbamate 
• 95-76-1 m,p-dichloroaniline 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 506-59-2 N,N-dimethylammonium chloride 
• 201230-82-2 carbon monoxide 
• 10248-88-1 N'-(3,4-dichloro-phenyl)-N,N-dimethyl-thiourea 

Downstream Products

• 85413-31-6 C₉H₉Cl₃N₂O 
• 124-40-3 dimethyl amine 
• 102-36-3 3,4-dichlorophenylisocyanate 
• 74-89-5 methylamine 
• 34637-13-3 N,N-dimethyl-N'-(3-chloro-4-hydroxy-phenyl)-urea 
• 3567-62-2 3-(3,4-Dichlorophenyl)-1-methylurea 
• 69342-26-3 N-(4-chloro-3-hydroxyphenyl)-N',N'-dimethylurea 
• 76409-92-2 N-(4,4-dichlorophenyl)-N'-formyl-N'-methylurea 
• 95-76-1 m,p-dichloroaniline 
• 61208-40-0 N-(3,4-dichlorophenyl)-N-ethylthio-N',N'-dimethyl-urea 
• 61208-44-4 N-(3,4-dichlorophenyl)-N-(2-chloroethylthio)-N',N'-dimethyl-urea 
• 61208-39-7 N-(3,4-dichlorophenyl)-N-isopropylthio-N',N'-dimethyl-urea 
• 61208-45-5 N-(3,4-dichlorophenyl)-N-(3-chloropropylthio)-N',N'-dimethyl-urea 
• 124-38-9 carbon dioxide 

Relevant articles and documents

Weeding composition compounded by fine glufosinate-ammonium and diuron and preparation method and application thereof

The invention provides a weeding composition compounded by fine glufosinate-ammonium and diuron. The weeding composition is characterized by comprising fine glufosinate-ammonium, diuron and other auxiliary agents, and the content of the fine glufosinate-ammonium is 1-60 parts by mass, the content of the diuron is 1-60 parts by mass, and the content of the auxiliary agents is 20-70 parts by mass. By reasonably proportioning the proportions of the fine glufosinate-ammonium and the diuron in the herbicide, the pesticide effect of the herbicide is enhanced, the control effect on weeds in uncultivated areas is superior to the activity of the singly applied components, meanwhile, the control spectrum of the weeds is expanded, the weeding effect is improved, the weeding composition has a prominent comprehensive control effect on gramineous weeds, cyperaceae weeds and broadleaf weeds, and has the advantages of fast effectiveness, long lasting period, delayed herbicide resistance, thorough weeding, low residue, low toxicity, safety, environmental protection and the like.

Synthesis method for diuron

The invention provides a synthesis method for diuron. The synthesis method for diuron comprises the following steps: dropwise adding pretreated 3,4-dichloro phenyl isocyanato toluene liquid into a dimethylamine toluene solution, wherein the temperature does not exceed 15 DEG C, pH of a dropwise adding end point is about 7-11, and the feeding molar ratio of 3,4-dichloro phenyl isocyanato to dimethylamine is 1: 1-3; and after dropwise adding is finished, carrying out suction filtration, and drying an obtained filter cake at the temperature of 90-100 DEG C to obtain a diuron technical product, wherein a solvent obtained after suction filtration is used for preparing the dimethylamine toluene solution after being recycled. Industrial operation steps for synthesis of the diuron are reduced, the purity and the yield are improved, wastewater is not produced in aftertreatment, and the cost is reduced.

Synthesis method of phenylurea herbicide or deuteration-labeled phenylurea herbicide

The invention relates to a synthesis method of a phenylurea herbicide or a deuteration-labeled phenylurea herbicide (a compound of a formula (I)). The compound of the formula (I) is obtained by reacting a compound of a formula (II) with a dimethylamine salt or D6-dimethylamine salt in the presence of an organic base. According to the synthesis method, the side reaction of substituted phenyl isocyanate and water or alcohol is avoided, the leakage of dimethylamine or dimethylamine-D6 is reduced, and the synthesis method has the advantages of simple operation, low requirements for equipment, low cost, high yield, and fewer by-products. The formula I is shown in the description.