122836-35-5

Basic information

• Product Name: SULFENTRAZONE
• Synonyms: 2′,4′-dichloro-5′-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)methanesulfonanilide;N-(2,4-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl)methanesulfonamide;SULFENTRAZONE,FMC 97285;Methanesulfonamide, N-2,4-dichloro-5-4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-ylphenyl-;2',4'-dichloro-5'-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl) methanesulfonanilide;Sulfentrazone standard;N-(2,4-dichloro-5-(4-(difluoroMethyl)-3-Methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phenyl)MethanesulfonaMide;FREE SAMPLE NCV SULFENTRAZONE TECHNICAL
• CAS NO: 122836-35-5
• Molecular Formula: C₁₁H₁₀Cl₂F₂N₄O₃S
• Molecular Weight: 387.19
• Mol File: 122836-35-5.mol

Chemical Properties

• Melting Point: 75-78°
• Boiling Point: 468.2 °C at 760 mmHg
• Flash Point: 237 °C
• Appearance: /
• Density: 1.72 g/cm³
• Vapor Pressure: 6.1E-09mmHg at 25°C
• Refractive Index: 1.646
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 6.56(at 25℃)
• CAS DataBase Reference: SULFENTRAZONE(CAS DataBase Reference)
• NIST Chemistry Reference: SULFENTRAZONE(122836-35-5)
• EPA Substance Registry System: SULFENTRAZONE(122836-35-5)

Safety Data

• RIDADR: UN3077 (solid); UN3082(liquid)
• Hazardous Substances Data: 122836-35-5(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
SULFENTRAZONE is used as a herbicide for controlling sedges in turfgrass. Its application helps maintain the quality and appearance of turfgrass by eliminating unwanted sedges that can compete with the grass for resources and space.
Used in Turfgrass Management:
In the turfgrass industry, SULFENTRAZONE is utilized as a selective herbicide to target and control sedges without causing significant harm to the desired grass species. This selective action allows for effective weed control while preserving the health and integrity of the turfgrass.

Trade name

AUTHORITY? Sulfentrazone; CANOPY XL?; COVER?; F6285?; FMC? 97285; GAUNTLET?; SPARTAN?; SULFENTRAZONE? (F6285) 4F; SULFENTRAZONE? (F6285) 75DF

Metabolic pathway

When 14C-sulfentrazone is applied to coffee senna and sicklepod through the roots, 83% of the parent compound remains in coffee senna leaf tissue after 9 h exposure and in contrast, sicklepod takes up relatively less sulfentrazone through the root and metabolizes sulfentrazone in the foliage more rapidly than coffee senna. The primary detoxification reaction appears to be oxidation of the methyl group on the triazolinone ring, resulting in the formation of the more polar hydroxymethyl derivative. The aniline analog is identified as a plant-specific metabolite. The tolerance of sicklepod to sulfentrazone is primarily due to a relatively high rate of metabolism of sulfentrazone compared with coffee senna. When 14C-sulfentrazone is administered orally to rats, goats, and hens in a daily diet, administered radioactivity is quantitatively excreted in the urine, feces, or hen excreta. In all of the species, unchanged sulfentrazone and two non-conjugated metabolites are found, which are 3-hydroxymethyl and carboxylic acid derivatives, the latter of which decomposes at high temperature or acidic pH to give the corresponding desmethyl analog of sulfentrazone. In rats, a minor reduction metabolite is detected which is tentatively characterized as the 2,3-dihydro-3-hydroxymethyl derivative.

InChI:InChI=1/C11H10Cl2F2N4O3S/c1-5-16-19(11(20)18(5)10(14)15)9-4-8(17-23(2,21)22)6(12)3-7(9)13/h3-4,10,17H,1-2H3

Upstream product

• 111992-18-8 2-(5-amino-2,4-dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one 
• 124-63-0 methanesulfonyl chloride 
• 111992-16-6 4,5-dihydro-3-methyl-4-difluoromethyl-1-(2,4-dichlorophenyl)-1,2,4-triazol-5(1H)-one 
• 109913-40-8 1-(2-chlorophenyl)-3-methyl-1H-1,2,4-triazol-5(4H)-one 
• 22863-24-7 1-phenyl-3-methyl-1H-1,2,4-triazol-5-one 
• 111992-17-7 4,5-dihydro-3-methyl-4-difluoromethyl-1-(2,4-dichloro-5-nitrophenyl)-1,2,4-triazole-5(1H)-one 
• 103998-84-1 2-(2-(2,4-dichlorophenyl)hydrazono)propanoic acid 
• 79604-49-2 4,5-dihydro-1-(2,4-dichlorophenyl)-3-methyl-1,2,4-triazol-5(1H)-one 
• 66-27-3 Methyl methanesulfonate 
• 1912-31-8 propyl methanesulfonate 
• 16156-53-9 isobutyl methanesulfonate 
• 3144-09-0 methanesulfonamide 
• 22863-24-7 5-methyl-2-phenyl-2,4-dihydro-[1,2,4]triazol-3-one 
• 554-00-7 2,4-Dichloroaniline 

Relevant articles and documents

Preparation method of sulfonyl carfentrazone-ethyl

The invention relates to a preparation method of sulfonyl carfentrazone-ethyl, which takes 2, 4-dichloroaniline as an initial raw material, and comprises the following steps of: 1, carrying out nitration reaction on a benzene ring of the 2, 4-dichloroaniline; as the N-difluoromethyl substituted triazolinone ring is formed, nitration and reduction reactions on the benzene ring can be carried out before the N-difluoromethyl substituted triazolinone ring is formed, and the N-difluoromethyl substituted triazolinone ring does not need to be placed in reaction environments such as mixed acid nitration and nitro reduction in the presence of concentrated sulfuric acid and concentrated nitric acid, so that the generation of byproducts is reduced, and the synthesis yield of the compound is improved; the production cost of the compound is reduced; and moreover, the problem that an N-difluoromethyl substituted triazolinone ring is unstable under certain nitrification conditions is also avoided, so that the nitrification and reduction methods have more choices, and a more advanced sulfonyl carfentrazone-ethyl production process is favorably developed.

PROCESSES FOR THE SYNTHESIS OF SULFENTRAZONE

Disclosed are processes for the synthesis of sulfentrazone, which provide a high conversion of sulfentrazone amine and high yield of the final sulfentrazone product.

Synthesizing method of sulfentrazone

The invention discloses a synthesizing method of sulfentrazone. The synthesizing method comprises the following steps of using a compound (II) as the raw material, and performing difluoro methylation,chlorination and bromination; then, performing methylsulfonylation, so as to obtain the final product of the sulfentrazone. The synthesizing method has the advantages that the obtained intermediate after chlorination is firstly brominated, and then the obtained intermediate after bromination and the methanesulfonamide are catalyzed by a catalyst to obtain the sulfentrazone; the chemical selectivity is high, and the dangerous technologies of nitrification, hydrogenation and the like in the traditional technology route are avoided; the production of a large amount of waste acid and waste waterin the nitrification process is avoided, the green effect is better, the efficiency is higher, and the safety and reliability are higher; the whole technology is simple and convenient, and the reaction conditions are mild; by adjusting the reaction conditions, the yield rate of the obtained product is high, the quality of the product is high, and the synthesizing method is suitable for industrialized production.

Method for preparing sulfentrazone through catalytic coupling of copper reagent

The invention relates to the field of organic synthesis, in particular to a method for preparing sulfentrazone through catalytic coupling of a copper reagent. The method comprises the steps of introducing boric acid or a boric acid ester group into benzen

Novel preparation method of sulfentrazone

The invention relates to the field of organic synthesis, and particularly relates to a novel preparation method of sulfentrazone. The novel preparation method comprises the following steps: performinga reaction on 2-(2,4-dichlorophenyl)-4-(difluoromethyl)

POLYMORPHS OF HERBICIDAL SULFONAMIDES

Solid polymorphic forms of sulfentrazone are described. Particularly, a new polymorphic form of sulfentrazone is described herein as sulfentrazone-1, having surprising property advantages over technical sulfentrazone. Processes for the preparation of sulfentrazone-1, herbicidal compositions comprising sulfentrazone-1, and methods of its use are described.

Method for synthesizing Sulfentrazone

The invention relates to a method for synthesizing Sulfentrazone. The method is characterized by comprising the steps of liberating o-chlorophenylhydrazine from o-chlorophenylhydrazine hydrochloride, which serves as a raw material, by an alkali, subjecting o-chlorophenylhydrazine to a reaction with trimethyl orthoacetate and potassium cyanate so as to obtain 1-o-chlorophenyl-3-methyl-1H-1,2,4-triazol-5-one, and then, subjecting 1-o-chlorophenyl-3-methyl-1H-1,2,4-triazol-5-one to N-alkylation, chlorination, nitration, reduction and sulfonylation, thereby obtaining the Sulfentrazone, wherein a composite catalyst and a solvent, i.e., dichloroethane are adopted in a chlorination reaction. The method for synthesizing the Sulfentrazone, disclosed by the invention, has the advantages that the o-chlorophenylhydrazine hydrochloride serves as the raw material, so that the steric hindrance of an intermediate product can be low, and the yield of the product is increased; and meanwhile, in the chlorination reaction, the composite catalyst is adopted, thus, the orientation effect on all atoms is good, and the solvent is dichloroethane, so that the recycling of the solvent is facilitated.

Method for synthesizing a sulphur grass amine intermediate and armor sulphur grass amine method

The invention discloses a method for synthesizing a sulfentrazone midbody and sulfentrazone. The method comprises the following steps: preparing the sulfentrazone midbody (III) from 1-phenyl-3-methyl-1H-1,2,4-triazole-5-ketone used as a raw material in an aprotic solvent in the presence of a compound (A) or a compound (B) and alkali, performing difluoro methylation to obtain a midbody (IV), performing chlorination, nitration and reduction, and further performing methyl sulfone chloride sulfonylation to obtain a final product, namely, N(2,4-difluoro-5-(4-difluoro methyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl) phenyl) sulfamide. The method has the main beneficial effects that due to an adopted catalytic hydrogenation process, the nitroreduction is not only high in chemical selectivity, but also is more environment-friendly, efficient, safe and reliable, as triphenylphosphine, polyethylene glycol or crown ether is used as a catalyst which takes the place of a conventional used catalyst such as DMF (Dimethyl Formamide) in the sulfonylation reaction, less side reaction is caused, and the yield is high. The overall process is simple and convenient, the reaction condition is gentle, the yield is high, the product quality is high, and the industrial production is facilitated.

A aryltriazolinones preparation method

The invention discloses a method for preparing aryl triazolinone. The method comprises the following steps: by taking aryl triazolinone as a raw material, taking an oxygen-containing gas or hydrogen peroxide water solution as an oxidant, and taking active carbon as a catalyst, performing oxidation reaction to obtain aryl triazolinone. By adopting the method, a new concept for the synthesis of the aryl triazolinone compound is provided, the hydrogen peroxide solution or the oxygen-containing gas is taken as the oxidant, the active carbon is taken as the catalyst, and the traditional processing modes of hypohalous acid and salt thereof, halogen oxidant or metal compound catalyst are substituted; the halogen and the metal compound are not contained in the wastewater, so that the environment is not polluted; when the optimized active carbon is adopted, the purity and the yield of the product are high. The environment pollution caused by the halogen-containing oxidant and the metal compound is avoided, the production process is clean, the reaction process is environmentally friendly, the product content and the yield are high and the economic and environmental protection benefits are obvious, so that the method is a scientific and environment-friendly novel method for producing the aryl triazolinone compound.