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| 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;annopyranosyl-L-threonine;DMU | | CAS: | 330-54-1 | | MF: | C9H10Cl2N2O | | MW: | 233.09 | | EINECS: | 206-354-4 | | Product Categories: | pesticide;Agro-Products;Aromatics;Bioactive Small Molecules;Building Blocks;Carbonyl Compounds;D;DAlphabetic;DIO - DIZMethod Specific;Cell Biology;Chemical Synthesis;DIG-DY;Organic Building Blocks;Ureas;Organics;ACTIVE AGROCHEMICAL INGREDIENTS;INSECTICIDE;2000/60/EC;Alpha sort;European Community: ISO and DIN;Pesticides&Metabolites | | Mol File: | 330-54-1.mol |  |
| | Diuron Chemical Properties |
| Melting point | 158-159°C | | Boiling point | 180-190°C | | density | 1.48 | | vapor pressure | 2(x 10-7 mmHg) at 30 °C (Hawley, 1981) | | 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. | | InChIKey | XMTQQYYKAHVGBJ-UHFFFAOYSA-N | | LogP | 2.84-2.89 at 20℃ and pH4.03-9 | | NIST Chemistry Reference | Urea, 3-(3,4-dichlorophenyl)-1,1-dimethyl-(330-54-1) | | EPA Substance Registry System | Diuron (330-54-1) |
| | Diuron Usage And Synthesis |
| 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 | A phenyl urea herbicide. Pre-emergent herbicide. | | Uses | 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: 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. It has a role as a herbicide, a photosystem-II inhibitor, a xenobiotic, an environmental contaminant and a mitochondrial respiratory-chain inhibitor. It is a dichlorobenzene and a 3-(3,4-substituted-phenyl)-1,1-dimethylurea.
| | 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 | 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. | | 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) ur
Incubation 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 d
The 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. |
| | Diuron Preparation Products And Raw materials |
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