74222-97-2

Basic information

• Product Name: DPX-T5648
• Synonyms: Oust 75DF;OUST WEED KILLER(R);sulfometuron-me;SULFOMETURON METHYL;SULFOMETURON METHYL ESTER;DPX-T5648;methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfamoyl]benzoate;METHYL 2(((((4,6-DIMETHYL-2-PYRIMIDINYL)-AMINO)CARBONYL)AMINO)SULFONYL)BENZOATE
• CAS NO: 74222-97-2
• Molecular Formula: C₁₅H₁₆N₄O₅S
• Molecular Weight: 364.38
• EINECS: 277-780-6
• Product Categories: HERBICIDE;SN - SZPesticides&Metabolites;Alpha sort;Environmental Standards;Herbicides;MetabolitesPesticides&Metabolites;Pesticides&Metabolites;Q-ZAlphabetic;S;Urea structure;NULL
• Mol File: 74222-97-2.mol

Chemical Properties

• Melting Point: 203-205°C
• Boiling Point: 197°C (rough estimate)
• Appearance: white solid
• Density: 1.48
• Refractive Index: 1.6000 (estimate)
• PKA: 5.7(at 25℃)
• CAS DataBase Reference: DPX-T5648(CAS DataBase Reference)
• NIST Chemistry Reference: DPX-T5648(74222-97-2)
• EPA Substance Registry System: DPX-T5648(74222-97-2)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN3077 9/PG 3
• WGK Germany: 2
• RTECS: DG9096550
• Hazardous Substances Data: 74222-97-2(Hazardous Substances Data)

Usage

Uses

Herbicide.

Definition

ChEBI: A benzoate ester that is the methyl ester of 2-{[(4,6-dimethylpyrimidin-2-yl)carbamoyl]sulfamoyl}benzoic acid.

Agricultural Uses

Herbicide: Used to control annual and perennial grasses and broadleaf weeds on landscapes, rights-of-ways, fence rows, forests, industrial structure areas and non-crop land. Not listed for use in EU countries. Registered for use in the U.S.

Trade name

DPX-T5648?; KNOCKOUT?; LANDMARK? MP (sulfometuron-methyl + chlorsulfuron); OUST?; OUSTAR?; RIVERDALE?; STAMPRO?

Environmental Fate

Soil. In unsterilized soils, 58% of 14C-labeled sulfometuron-methyl degraded after 24 weeks. Metabolites identified were 2,3-dihydro-3-oxobenzisosulfonazole (saccharin), methyl-2-(aminosulfonyl)benzoate, 2-aminosulfonyl benzoic acid, 2-(((aminocarbonyl)amino)sulfonyl)benzoate and [14C]carbon dioxide. The rate of degradation in aerobic soils was primarily dependent upon pH and soil type (Anderson and Dulka, 1985). The reported half-life in soil was approximately 4 weeks (Hartley and Kidd, 1987). Chemical/Physical. Sulfometuron-methyl is stable in water at pH values of 7 to 9 but is rapidly hydrolyzed at pH 5.0 forming methyl 2-(aminosulfonyl)benzoate and saccharin. When sulfometuron-methyl in an aqueous solution was exposed to UV light (λ = 300–400 nm), it degraded to the intermediate methyl benzoate which then mineralized to carbon dioxide (Harvey et al., 1985). The hydrolysis half-lives of metsulfuron-methyl at pH 5 and 25 and 45°C were 33 and 2.1 days, respectively. At pH 7 and 45°C, the hydrolysis half-life is 33 days (Beyer et al., 1988).

Metabolic pathway

Sulfometuron methyl is relatively stable at neutral and basic pH and undergoes cleavage of the sulfonylurea linkage to yield methyl-2-(aminosulfonyl)benzoate and 4,6-dimethyl-2-aminopyrimidine as major hydrolysis products, and saccharin as the terminal product. These products are also observed as major degradation products in soils. In plants, monohydroxymethylsulfometuron methyl is the primary metabolite which is also identified as a mammalian and soil metabolite and undergoes further degradation by mammals to give 2-amino-4-hydroxymethyl-6- methylpyrimidine.

InChI:InChI=1/C14H15N5O5S/c1-8-15-9(2)17-13(16-8)18-14(21)19-25(22,23)11-7-5-4-6-10(11)12(20)24-3/h4-7H,1-3H3,(H2,15,16,17,18,19,21)

Upstream product

• 767-15-7 2-Amino-4,6-dimethylpyrimidine 
• 74222-95-0 2-(methoxycarbonyl)benzenesulfonyl isocyanate 
• 67359-63-1 N-(methylcarboxy)-o-carbomethoxybenzenesulfonamide 
• 25543-09-3 methyl 3-oxo-2,3-dihydrobenzo[d][1,2]thiazol-2-carboxylate 1,1-dioxide 
• 81-07-2 saccharin 
• 26638-43-7 2-methoxycarbonylbenzenesulfonyl chloride 

Downstream Products

• 74223-56-6 2-[[[[(4,6-dimethyl-2-pyrimidinyl)-amino]carbonyl]amino]sulfonyl]-benzoic acid 

Relevant articles and documents

A NOVEL FORM OF SULFOMETURON METHYL, A PROCESS FOR ITS PREPARATION AND USE THE SAME

A new crystalline form of sulfometuron methyl of formula (I), the crystal preparation process, the analyses of the crystal through various analytical methods and using the crystal to prepare stable agrochemical formulation. The invention also describes the use of various solvents towards the crystalline form preparation conditions. The novel crystal form is particularly suitable for use in herbicidal compositions and in the control of unwanted plant growth.

A 2 - (4,6-dimethyl-pyrimidin-2-yl-carbamoyl amino sulfonyl) benzoic acid synthesis of methyl

The invention discloses a synthetic method of 2-(4, 6-dimethyl pyrimidine-2-base amino formyl amino sulfonyl) methyl benzoate. The method is characterized in that gluside and dimethyl carbonate are adopted for preparing an intermediate of N-methyl formate-o-sulfonylbenzoylimine, and then methanol is adopted for preparing an intermediate of o-methoxy carboxide benzenesulfonamide methyl formate. The purity of 2-(4,6-dimethyl pyrimidine-2-base amino formyl amino sulfonyl) methyl benzoate prepared by the synthetic method provided by the invention reaches more than 95.0%, and the total yield reaches 55.0%. The method is mainly applied to preparation of 2-(4, 6-dimethyl pyrimidine-2-base amino formyl amino sulfonyl) methyl benzoate and has the advantages that raw materials are cheap and easy to obtain, the technology is simple, the three wastes are few, virulent suffocating gas is prevented from being used, and the method is suitable for batch industrialized production.

Halopyridyl triazolinone herbicides and herbicidal use thereof

Disclosed are herbicidal halopyridyl triazolinones, herbicidal compositions comprising the halopyridyl triazolinones, and herbicidal use of the compounds and compositions. Such compounds and compositions are useful as both preemergence and postemergence herbicides in a variety of crops.

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.

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.

Agricultural sulfonamides

N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted in the 2-position by a carboxy radical, ester, thioester, or amide thereof; e.g. N-[(4,6-dimethylpyrimidin-2-yl)-aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide or N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.

Herbicidal complexes with ureas

Water-soluble complexes, which have herbicidal utility, can be formed from urea and alkali metal salts of selected sulfonylureas, e.g., chlorsulfuron.

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.

Agricultural sulfonamides

N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted in the 2-position by a carboxy radical, ester, thioester, or amide thereof; e.g. N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide or N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.