ChemicalBook--->CAS DataBase List--->90982-32-4

90982-32-4

90982-32-4 Structure

90982-32-4 Structure
IdentificationMore
[Name]

Chlorimuron-ethyl
[CAS]

90982-32-4
[Synonyms]

2-[[[[(4-Chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic acid ethyl ester
Chlorimuron Et
CHLORIMURON-ETHYL
chlorimuron ethyl ester
CLASSIC
CLASSIC 25 DF WEED KILLER(R)
classic 75df
DARBAN
DPX-F6025
ETHYL-2-[[[[(4-CHLORO-6-METHOXY-2-PYRIMIDINYL)AMINO]CARBONYL]AMINO]-SULFONYL] BENZOATE
2-(((((4-chloro-6-methoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)benzoica
ethyl2-(((((4-chloro-6-methoxpyrimidin-2-yl)aminol)carbonyl)amino)sulfonyl)benzoate
ethyl2-(((((4-chloro-6-methoxypyrimidin-2-yl)-amino)carbonyl)amino)sulfonyl)b
Ethyl2-(((((4-chloro-6-methoxypyrimidin-2-yl)amino)carbonyl)amino)sulfonyl)benzoate
CHLORIMURON ETHYL, 100MG, NEAT
Classic[R]
Benzoic acid, 2-(4-chloro-6-methoxy-2-pyrimidinyl)aminocarbonylaminosulfonyl-, ethyl ester
Chlorsulfuron-ethyl
Ethyl 2-(4-chloro-6-methoxypyrimidin-2-ylcarbamoyl sulfamcyl benzoate
Chlorimuron W.P.
[EINECS(EC#)]

618-690-2
[Molecular Formula]

C15H15ClN4O6S
[MDL Number]

MFCD00128063
[Molecular Weight]

414.82
[MOL File]

90982-32-4.mol
Chemical PropertiesBack Directory
[Appearance]

Colorless to off white or pale yellow crystals or powder. Some formulations are listed as “flammable” in the literature. Odorless.
[Melting point ]

180-182°C
[density ]

1.4727 (rough estimate)
[refractive index ]

1.6100 (estimate)
[storage temp. ]

0-6°C
[solubility ]

Freely soluble in aqueous solution
[form ]

Solid
[pka]

3.78±0.10(Predicted)
[color ]

White to Light Yellow
[Water Solubility ]

1.018mg/L(temperature not stated)
[Henry's Law Constant]

5.5×109 mol/(m3Pa) at 25℃, HSDB (2015)
[Stability:]

Unstable in DMSO solution
[Major Application]

agriculture
environmental
[InChI]

1S/C15H15ClN4O6S/c1-3-26-13(21)9-6-4-5-7-10(9)27(23,24)20-15(22)19-14-17-11(16)8-12(18-14)25-2/h4-8H,3H2,1-2H3,(H2,17,18,19,20,22)
[InChIKey]

NSWAMPCUPHPTTC-UHFFFAOYSA-N
[SMILES]

CCOC(=O)c1ccccc1S(=O)(=O)NC(=O)Nc2nc(Cl)cc(OC)n2
[CAS DataBase Reference]

90982-32-4(CAS DataBase Reference)
[EPA Substance Registry System]

90982-32-4(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36:Irritating to the eyes.
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[RIDADR ]

UN3077 (solid)
[WGK Germany ]

WGK 3
[RTECS ]

DG5095000
[REACH Registrations]

Inactive
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Aquatic Acute 1
Aquatic Chronic 1
[Hazardous Substances Data]

90982-32-4(Hazardous Substances Data)
[Toxicity]

LD50 in male, female rats (mg/kg): 4102, 4236 orally (Claus)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Dichloromethane-->Toluene-->Sodium carbonate-->Triethylamine-->Sodium bicarbonate-->Oxalyl chloride-->Dimethyl malonate-->4,6-Dihydroxypyrimidine-->Saccharin sodium-->2,4-Dichloropyrimidine-->4,6-Dichloropyrimidine-->o-Ethoxycarbonylbenzenesulfonamide-->Pyrimidine, 2-isocyanato- (9CI)
Hazard InformationBack Directory
[General Description]

Colorless crystals. Used as an herbicide.
[Reactivity Profile]

CHLORIMURON ETHYL is a sulfonyl urea, and pyrimidine derivative.
[Potential Exposure]

A sulfonylurea/pyrimidine derivative herbicide used to control broadleaf weeds and annual morning glory in soybeans and peanuts. Not listed as registered for use in EU countries. Registered for use in the United States and available from more than 25 global suppliers.
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions) if breathing has stopped, and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
[Shipping]

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
[Incompatibilities]

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, nitrates.
[Chemical Properties]

Colorless to off white or pale yellow crystals or powder. Some formulations are listed as “flammable” in the literature. Odorless.
[Waste Disposal]

Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
[Uses]

Herbicide.
[Definition]

ChEBI: Chlorimuron-ethyl is an ethyl ester resulting from the formal condensation of the carboxy group of chlorimuron with ethanol. A proherbicide for chloimuron, it is used as herbicide for the control of broad-leaved weeds in peanuts, soya beans, and other crops. It has a role as a proherbicide, an EC 2.2.1.6 (acetolactate synthase) inhibitor and an agrochemical. It is a sulfamoylbenzoate, a N-sulfonylurea, an aromatic ether, an ethyl ester, an organochlorine pesticide and a member of pyrimidines. It is functionally related to a chlorimuron. It is a conjugate acid of a chlorimuron-ethyl(1-).
[Production Methods]

Chlorimuron-ethyl is commercially produced via a convergent multi-step synthesis starting from 2-amino-4-chloro-6-methoxy-pyrimidine, which is sulfonylated with 2-(ethoxycarbonyl)benzenesulfonyl chloride under basic conditions to form the sulfonamide linkage. The intermediate undergoes condensation with ethyl chloroformate and phosgene or carbonyl diimidazole to construct the urea bridge, followed by cyclisation with ethyl 2-isocyanatoacetate or direct coupling with ethyl chloroformate-activated glycine to yield the pyrimidinyl urea core. Final esterification and purification by recrystallisation produce chlorimuron-ethyl.
[Agricultural Uses]

Herbicide: Used to control broadleaf weeds and annual morning glory in soybeans and peanuts. Not listed as registered for use in EU countries. Registered for use in the U.S., except California. There are more than 25 global suppliers.
[Trade name]

AUTHORITY®; CANOPY® (chlorimuron-ethyl + Metribuzin); CLASSIC®; CONCERT® cancelled; DPX-F6025®; GEMINI®[C]; LOROX®[C]; PREVIEW®[C]; RELIANCE®; SKERMISH®, cancelled; SYNCHRONCY®; SYNCHRONY®[C]
[Mechanism of action]

Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS
[Metabolic pathway]

Excised soybean seedlings rapidly metabolize 14C- chlorimuron ethyl, but common cocklebur and redroot pigweed, which are sensitive to chlorimuron ethyl, metabolize much more slowly. Two metabolites are primarily identified. By intact corn seedlings, chlorimuron ethyl undergoes biotransformation to give more metabolites and under UV light is photodegraded into smaller fragments.
[Pesticide Type]

Herbicide
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

2-[[[[(4-Chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic acid ethyl ester(90982-32-4).msds
Questions And AnswerBack Directory
[Description]

Chlorimuron-ethyl is a kind of post-emergence, foliar applied herbicide which is used without the EU regulatory approval. As an herbicide belonging to the sulfonylurea family, it is commonly used to control the weeds associated with wheat, rice, soybean, barley, potato, and corn. It has advantages of being broad-spectrum, having low use rate, having good crop selectivity as well as being of low toxicity to animals. Its mechanism of action is through suppressing the plant- and microbial-specific enzyme acetolactate synthase (ALS), further blocking the biosynthesis of branched-chain amino acids such as valine, leucine and isoleucine. Through this mechanism, it cause rapid cessation of plant cell division and growth. 
[References]

http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1145.htm
http://lfse.iae.ac.cn/Article/UploadFiles/201310/2013102910313432.pdf
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

90982-32-4(sigmaaldrich)
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