330-54-1

Hazards Identification

Pictogram(s):

Signal:

Warning

GHS Hazard Statements:

H302: Harmful if swallowed [Warning Acute toxicity, oral]
H351: Suspected of causing cancer [Warning Carcinogenicity]
H373 **: Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes:

P203, P260, P264, P270, P273, P280, P301+P317, P318, P319, P330, P391, P405, and P501

Hazard Classes and Categories:

Carc. 2
Acute Tox. 4 *
STOT RE 2 *
Aquatic Acute 1
Aquatic Chronic 1
Acute Tox. 4 (100%)
Carc. 2 (100%)
STOT RE 2 (100%)
Aquatic Acute 1 (98.44%)
Aquatic Chronic 1 (100%)
Carcinogenicity - category 2
Acute toxicity - category 4
Specific target organ toxicity (repeated exposure) - category 2
Hazardous to the aquatic environment (acute) - category 1
Hazardous to the aquatic environment (chronic) - category 1
Acute toxicity (Oral) - Category 5
Skin corrosion/irritation - Category 3
Serious eye damage/eye irritation - Category 2B
Specific target organ toxicity - Single exposure - Category 3 (Respiratory tract irritation)
Specific target organ toxicity - Repeated exposure - Category 2 (blood)
Hazardous to the aquatic environment (Acute) - Category 1
Hazardous to the aquatic environment (Long-term) - Category 1

Hazards Summary:

Urea-derived herbicides have low toxicity in animal feeding studies; May induce methemoglobinemia; [HSDB] Systemic toxicity unlikely unless large amounts ingested; [EPA Pesticides, p. 122] Skin and mucous membrane irritation have been reported with the use of diuron. [ACGIH]

Usage

Air & Water Reactions

Very slightly soluble in water.

Reactivity Profile

Diuron is incompatible with the following: Strong acids .

Health Hazard

INHALATION: May cause irritation of nose and throat. EYES: Irritation. SKIN: Moderately irritating to skin.

Health Hazard

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.

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

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 
• 1746-01-6 2,3,7,8-Tetrachloro-dibenzo[1,4]dioxine 
• 51207-31-9 2,3,7,8-Tetrachlorodibenzofuran 
• 95-76-1 m,p-dichloroaniline 
• 7159-94-6 ethyl (3,4-dichlorophenyl)carbamate 
• 67-56-1 methanol 
• 1225439-19-9 3-(1H-1,2,3-triazol-4-yl)propanoic acid 

Relevant academic research and scientific papers

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.

NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND

An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.

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.

Process for synthesizing high-quality diuron

The invention relates to a process for synthesizing high-quality diuron. The process includes steps of adding toluene and 40% of dimethylamine into a cold synthesis kettle; dropwise adding 3. 4 dichlorobenzene into the cold synthesis kettle at the temperature of 25 DEG C approximately; preserving heat for half an hour after the 3. 4 dichlorobenzene is completely dropwise added into the cold synthesis kettle; placing the cold synthesis kettle in a heat synthesis kettle and increasing the temperature of the heat synthesis kettle until the temperature of the heat synthesis kettle reaches 85 DEG C; carrying out reaction to obtain diuron; centrifugally washing and drying the diuron. The process has the advantages that the process is low in raw material consumption and cost, free of wastewater and favorable for environmental protection, the conversion rate of the high-quality diuron can reach 98.5% at least, and the purity of the high-quality diuron can reach 99.3% at least.

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.

Technology for purifying diuron

The invention provides a technology for purifying diuron. The method includes the following steps that 3,4-methylbenzene dichlorophenyl isocyanate liquid is transferred into a reaction kettle first, and 30%-40% of dimethylamine aqueous solution is dripped into the reaction kettle; then a solution at the reaction endpoint is transferred into a primary solvent removal tower; the temperature of the primary solvent removal tower is raised; the solution subjected to solvent removal is transferred into a kettle liquid bath from the bottom of the solvent removal tower, standing and layering are carried out, and then filtering is performed; afterwards, the filtered solution is transferred into a secondary solvent removal tower; the solution subjected to solvent removal is transferred into a third-level solvent removal tower; at last, a diuron solution is extracted from the side line of the third-level solvent removal tower, and then is added with water and dried, and accordingly the purified diuron can be obtained. By the adoption of the production technology, a large amount of solvent in the production process of the diuron can be removed, and the purity of the diuron is improved to 98.2%.

Rhodium(iii)-catalysed aerobic synthesis of highly functionalized indoles from N-arylurea under mild conditions through C-H activation

A Rh(iii) catalysed amino arylation of alkynes using copper as the terminal oxidant for regeneration of the catalytically active species under aerobic conditions is described. This novel C-H activation reaction was applied to the synthesis of a wide range of substituted indoles from N-arylureas.

Improved method for the preparation of 1,1-dimethyl-3-arylureas using chlorocarbonylsulfenyl chloride

A convenient procedure for preparing some arylureas having herbicidal properties is reported. The method has two steps: (1) reaction of arylamine with chlorocarbonylsulfenyl chloride in the presence of nonpolar solvent to produce aryl carbonylsulfenyl chloride and (2) reaction with dimethylamine in a two-phase reaction catalysed by phase-transfer catalyst to produce the corresponding aryl ureas. Taylor & Francis Group, LLC.

Preparation of N,N-Dimethyl-N′-arylureas using S,S-dimethyl dithio-carbonate as a carbonylating reagent

A new, general method for the preparation of N,N-di-methyl-N′- arylureas using S,S-dimethyl dithiocarbonate as a phosgene substitute is reported. The method has been set up according to four procedures, all including three steps: (1) reaction of S,S-di- methyl dithiocarbonate with dimethylamine to give S-methyl N,N-dimethylthiocarbamate; (2) halogenation with various halogenating reagents (chlorine, methanesulfenyl chloride, bromine, and meth-anesulfenyl bromide) to give N,N-dimethylcarbamoyl chloride or bromide; (3) in situ reaction with primary arylamines. All the target products were obtained in high yields (85-98%; 16 reactions, average yield 93%) and with high purity. Also noteworthy is the recovery of byproducts of industrial interest, namely methanethiol and dimethyl disulfide, with complete exploitation of the reagent S,S- dimethyl dithiocarbonate. Georg Thieme Verlag Stuttgart.

Phenylureas. Part 1. Mechanism of the basic hydrolysis of phenylureas

The mechanism of the hydrolytic decomposition of phenylureas in basic media in the pH range 12 to 14 is investigated. In this pH range a levelling of the rate-pH curve is observed as well as a change of the substituent influence on the hydrolysis rate. These experimental findings suggest the formation of an unreactive side product of the phenylurea in a parasitic side equilibrium at sufficiently high pH. The urea dissociates at the aryl-NH group to give its conjugate base. For the hydrolytic decomposition of phenylureas an addition-elimination mechanism is proposed as has been established for the alkaline hydrolysis of carboxylic acid esters and amides.