74222-95-0

Usage

Uses

Used in Agricultural Industry:
Methyl 2-(isocyanatosulphonyl)benzoate is used as a key intermediate in the synthesis of Metsulfuron (M227745) for its herbicidal properties. This herbicide is effective in controlling pests and protecting crops and produce, ensuring a healthy and productive agricultural yield.
In the synthesis process, methyl 2-(isocyanatosulphonyl)benzoate plays a crucial role in the formation of the active ingredient Metsulfuron, which is then formulated and applied to agricultural fields to manage weed growth and safeguard crops from damage. The use of this intermediate in the production of Metsulfuron highlights its importance in the development of effective and targeted herbicides for modern agriculture.

InChI:InChI=1/C9H7NO5S/c1-15-9(12)7-4-2-3-5-8(7)16(13,14)10-6-11/h2-5H,1H3

Upstream product

• 57683-71-3 methyl 2-(aminosulfonyl)benzoate 
• 111-36-4 n-butyl isocyanide 
• 81-07-2 saccharin 
• 79-37-8 oxalyl dichloride 
• 2757-23-5 chloro(chlorosulfanyl)methanone 
• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 74223-64-6 Metsulfuron-methyl 

Downstream Products

• 101200-48-0 tribenuron methyl 
• 74223-63-5 N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide 
• 74222-97-2 Sulfometuron methyl 
• 74224-24-1 2-[(5,6-dimethyl-[1,2,4]triazin-2-ylcarbamoyl)-sulfamoyl]-benzoic acid methyl ester 
• 97780-06-8 2-[[(4-ethoxy-6-methylamino-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid,methyl ester 
• 128569-20-0 C₁₄H₁₃ClN₄O₆S 
• 1416567-40-2 C₁₄H₁₃BrN₄O₆S 
• 90707-92-9 methyl 2-<<(3-methoxy-1-methyl-1H-1,2,4-triazol-5-yl)aminocarbonyl>aminosulfonyl>benzoate 
• 74223-64-6 Metsulfuron-methyl 

Relevant academic research and scientific papers

Production process for improving quality of sulfonyl isocyanate

The invention discloses a production process for improving the quality of sulfonyl isocyanate. The production process comprises the steps of mixing a sulfanilamide raw material and xylene according toa certain ratio to form a sulfanilamide solution, adding a certain amount of xylene into a synthesis kettle, heating, controlling the temperature at 110 to 115 DEG C, adding the sulfanilamide solution into the synthesis kettle through a transfer pump at a certain rate; dropwise adding a catalyst and introducing gaseous phosgene at the same time, paying attention to that the catalyst must be dropwise added 2 hours before the sulfanilamide solution is well converted, reducing the phosgene flow until the process requirement cumulant is reached, transferring a product into a light breaking kettleafter heat preservation is performed for 2 hours, removing redundant phosgene by using nitrogen, and finally obtaining a finished product after qualified sampling and analyzing. According to the invention, the synthesis system of sulfonyl isocyanate is optimized, the yield of sulfonyl isocyanate is improved, and meanwhile, the synthesized tail gas and the gas-driving tail gas are innovatively condensed by a condenser and then flow back to the synthesis kettle, so that the tail gas is recycled, and the reaction rate and content of the product are improved.

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.

Synthetic process of metsulfuron-methyl-D3

The invention provides a synthesis process of metsulfuron-methyl-D3, comprising the following steps: Step 1), adding a compound I in an ethanol solution of sodium ethoxide to prepare a compound II; Step 2), adding the compound II prepared in the Step 1) into a tetrahydrofuran solution of deuterated sodium methoxide, and refluxing to obtain a compound III; Step 3), suspending a compound IV in anhydrous toluene, dropwise adding a compound V, adding triethylene diamine, and heating to prepare a toluene solution of a compound VI; and Step 4), suspending the compound III prepared in the Step 2) in ethyl acetate in under nitrogen protection, heating and dropwise adding the toluene solution of the compound VI that is obtained in the Step 3), and reacting to prepare the final product metsulfuron-methyl-D3. The invention has the following technical effects: by conversion of the functional group of a relatively-cheap compound I, the compound III is synthesized; although the yield is low, cumbersome multi-step synthesis and the use of a large amount of expensive deuterated methanol are avoided.

Sulfonylureas have antifungal activity and are potent inhibitors of Candida albicans acetohydroxyacid synthase

The sulfonylurea herbicides exert their activity by inhibiting plant acetohydroxyacid synthase (AHAS), the first enzyme in the branched-chain amino acid biosynthesis pathway. It has previously been shown that if the gene for AHAS is deleted in Candida albicans, attenuation of virulence is achieved, suggesting AHAS as an antifungal drug target. Herein, we have cloned, expressed, and purified C. albicans AHAS and shown that several sulfonylureas are inhibitors of this enzyme and possess antifungal activity. The most potent of these compounds is ethyl 2-(N-((4-iodo-6-methoxypyrimidin-2-yl)carbamoyl) sulfamoyl)benzoate (10c), which has a Ki value of 3.8 nM for C. albicans AHAS and an MIC90 of 0.7 μg/mL for this fungus in cell-based assays. For the sulfonylureas tested there was a strong correlation between inhibitory activity toward C. albicans AHAS and fungicidal activity, supporting the hypothesis that AHAS is the target for their inhibitory activity within the cell.

Collection of ion-trap mass spectre of sulfonylurea pyrolysis products

The pyrograms of 14 sulfonylureas, i.e. herbicides characterized by high biological activity and low application dose are discussed and the mass spectra of over 30 relevant pyrolysis products as obtained with a heated filament pyrolyzer interfaced to a capillary gas chromatograph/ion-trap detector mass spectrometer are presented. Such a data compilation is useful for diagnostic purposes for both intact sulfonylureas and their metabolites after degradation in soil, because metabolites and pyrolysis products are often identical and most of their mass spectra are lacking in commercially available mass spectral libraries. The performance of the ion-trap detector based on the quality of the mass spectra is briefly discussed.

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.

Process for the production of arylsulfonyl isocyanates

Arylsulfonyl isocyanates are prepared by reaction of an arylsulfonylamine with thionyl chloride and chlorocarbonylsulfenyl chloride in the presence of a catalytic amount of a tertiary base. The isocyanates may be used as intermediates in the production of herbicides or pharmaceutically active compounds.

Herbicidal ureas and isoureas

This invention relates to novel urea and isourea compounds, agricultural compositions containing them and to their method of use as pre- and post-emergence herbicides and to plant growth regulants.

Herbicidal N-(pyridinylaminocarbonyl)benzenesulfonamides

N-(Pyridinylaminocarbonyl)benzenesulfonamides are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.

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.