90982-32-4

Basic information

• Product Name: Chlorimuron-ethyl
• Synonyms: 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;ETHYL-2-[[[[(4-CHLORO-6-METHOXY-2-PYRIMIDINYL)AMINO]CARBONYL]AMINO]-SULFONYL] BENZOATE;DARBAN;DPX-F6025;Chlorimuron Et
• CAS NO: 90982-32-4
• Molecular Formula: C₁₅H₁₅ClN₄O₆S
• Molecular Weight: 414.82
• Product Categories: HERBICIDE
• Mol File: 90982-32-4.mol

Chemical Properties

• Melting Point: 180-182°C
• Appearance: colorless crystal
• Density: 1.4727 (rough estimate)
• Refractive Index: 1.6100 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Freely soluble in aqueous solution
• PKA: 3.78±0.10(Predicted)
• Water Solubility: 1.018mg/L(temperature not stated)
• Stability: Unstable in DMSO solution
• CAS DataBase Reference: Chlorimuron-ethyl(CAS DataBase Reference)
• NIST Chemistry Reference: Chlorimuron-ethyl(90982-32-4)
• EPA Substance Registry System: Chlorimuron-ethyl(90982-32-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36
• RIDADR: UN3077 (solid)
• RTECS: DG5095000
• Hazardous Substances Data: 90982-32-4(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Chlorimuron-ethyl is used as a herbicide for weed control in various crops such as wheat, rice, soybean, barley, potato, and corn. It is favored for its broad-spectrum activity, low use rate, good crop selectivity, and low toxicity to animals.
The application reason for Chlorimuron-ethyl in agriculture is its effectiveness in controlling broadleaf weeds and annual morning glory in soybeans and peanuts. It is registered for use in the U.S., except for California, and there are more than 25 global suppliers. However, it is not listed as registered for use in EU countries.
Its mechanism of action involves suppressing the plantand microbial-specific enzyme acetolactate synthase (ALS), which in turn blocks the biosynthesis of branched-chain amino acids like valine, leucine, and isoleucine. This leads to a rapid cessation of plant cell division and growth, effectively controlling weed populations in agricultural settings.

References

http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1145.htm http://lfse.iae.ac.cn/Article/UploadFiles/201310/2013102910313432.pdf

Reactivity Profile

Chlorimuron-ethyl is a sulfonyl urea, and pyrimidine derivative.

Trade name

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

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.

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.

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.

InChI:InChI=1/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)

Downstream Products

• 155-90-8 4-methoxypyrimidin-2-amine 
• 5734-64-5 2-amino-4-chloro-6-methoxypyrimidine 
• 59777-72-9 ethyl 2-(aminosulfonyl)benzoate 
• 81-07-2 saccharin 
• 99283-00-8 chlorimuron 

Relevant articles and documents

Substituted pyridinesulfonamide compounds or their salts, process for preparing the same, and herbicides containing the same

A substituted pyridinesulfonamide compound or its salt represented by the following general formula (I): wherein R1 is an unsubstituted or substituted alkyl group; R2 is an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group; and X and Y are each independently a member selected from the group consisting of alkyl groups and alkoxy groups, is disclosed. This compound is useful as the effective ingredient of a herbicide showing a wide weed-control spectrum even if used in a small amount.

Soybean plants with dominant selectable trait for herbicide resistance

The utilization of a positive selection seed screening process to isolate rate variants with resistance to a herbicide is described. The ability to screen large numbers of mutagenized seed has made it feasible to pursue and isolate plants with low frequency dominant herbicide-resistance mutations. The dominant herbicide resistance mutations are useful for many applications including expanding the utility of sulfonylurea herbicides for soybean weed control, production of F1 and F2 seeds, and as selectable markers for efficient seed purification.

N-phenylpyrrolidines

The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives of the formula I below are suitable for protecting crop plants against the phytotoxic action of herbicides and for regulating the plant growth. The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives are those of the formula I STR1 wherein A is --COOR1, --COSR1, --COO? M≈, --CONR2 R3 or --COCl; R1 is hydrogen, C1 -C4 alkyl, C2 -C6 alkenyl or C2 -C6 alkynyl; R2 and R3 independently of one another are hydrogen, C1 -C4 alkyl or C3 -C7 cycloalkyl; or R2 and R3 together with the nitrogen atom to which they are bonded are a saturated 3- to 7-membered heterocycle which can contain an additional hetero atom selected from the group comprising O, N and S and which is unsubstituted or up to trisubstituted by C1 14 C4 alkyl; and M≈ is the equivalent of an alkali metal cation or an alkaline earth metal cation or HN≈ (R2)3, and their isomers in optically pure or enriched form.

Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase

A nucleic acid fragment encoding a herbicide-resistant plant acetolactate synthase protein is disclosed. This nucleic acid fragment contains at least one nucleotide mutation resulting in one amino acid change in one of seven substantially conserved regions of acetolactate synthase amino acid homology. This mutation results in the production of an acetolactate synthase protein which is resistant to sulfonylurea herbicide compounds compared to the wild-type protein. Transformation of herbicide sensitive plants or plant cells with the fragment results in resistance to the herbicide.

Herbicidal compound concentrate

There is provided a novel herbicidal compound concentrate in the form of compressed solid formulations that disintegrate in water to form a sprayable dispersion.

Process for preparing sulfonylureas

Sulfonylureas are prepared by contacting a sulfonyl halide with an ammonium, phosphonium, sulfonium, or an alkali metal cyanate salt in the presence of an amine.