100784-20-1

Basic information

• Product Name: Halosulfuron methyl
• Synonyms: Halosulfuron-Methy;Halosulfuron-m;-1-methyl-1H-pyrazole-4-carboxylate;Methyl 3-chloro-5-(N-((4,6-dimethoxypyrimidin-2-yl);sulfamoyl);3-Chloro-5-[[3-(4,6-dimethoxypyrimidin-2-yl)ureido]sulfonyl]-1-methyl-1H-pyrazole-4-carboxylic Acid Methyl Ester;Methyl 3-Chloro-5-[[3-(4,6-dimethoxypyrimidin-2-yl)ureido]sulfonyl]-1-methyl-1H-pyrazole-4-carboxylate;SEMPRA(R)
• CAS NO: 100784-20-1
• Molecular Formula: C13H15ClN6O7S
• Molecular Weight: 434.81
• Product Categories: Herbicide
• Mol File: 100784-20-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 175-177°C
• Appearance: White powder
• Density: 1.618
• Refractive Index: 1.663
• Storage Temp.: 0-6°C
• PKA: 11.96±0.70(Predicted)
• Water Solubility: Insoluble in water
• Merck: 14,4602
• CAS DataBase Reference: Halosulfuron methyl(CAS DataBase Reference)
• NIST Chemistry Reference: Halosulfuron methyl(100784-20-1)
• EPA Substance Registry System: Halosulfuron methyl(100784-20-1)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN3077 9/PG 3
• WGK Germany: 3
• RTECS: UQ6392606
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 100784-20-1(Hazardous Substances Data)

Usage

Uses

Herbicide.

Hazard

Moderately toxic by ingestion.

InChI:InChI=1/C13H15ClN6O7S/c1-20-10(8(9(14)18-20)11(21)27-4)28(23,24)19-13(22)17-12-15-6(25-2)5-7(16-12)26-3/h5H,1-4H3,(H2,15,16,17,19,22)

Upstream product

• 36315-01-2 4,6-dimethoxy-2-aminopyrimidine 
• 100784-27-8 3-chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide 
• 109056-72-6 methyl 3-chloro-5-mercapto-1-methyl-1H-pyrazole-4-carboxylate 
• 109056-69-1 methyl 3,5-dichloro-1-methyl-1H-pyrazole-4-carboxylate 
• 148934-66-1 methyl 3-chloro-1-methylpyrazole-4-carboxylate 
• 64182-19-0 methyl 3-amino-1-methylpyrazole-4-carboxylate 
• 5952-93-2 methyl ester of 1-methylpyrazole-4-carboxylic acid 
• 88398-85-0 Methyl 5-Chloro-1-methylpyrazole-4-carboxylate 
• 89392-03-0 O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate 

Downstream Products

• 1048337-28-5 C₁₂H₁₄ClN₅O₄ 
• 100784-27-8 3-chloro-4-methoxycarbonyl-1-methylpyrazole-5-sulfonamide 

Related news

Electro-oxidation of herbicide Halosulfuron methyl (cas 100784-20-1) on glassy carbon electrode and applications08/10/2019

Halosulfuron methyl, a fast-acting herbicide and is absorbed into leaf tissue within 1–2 days and translocated through the vascular system, interrupting amino acid production within the plant, can be detected using glassy carbon electrode the technique of adsorptive stripping voltammetry. The a...detailed

Relevant articles and documents

Evaluation of Synthesis of Methyl 3-Chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate Using Green Metrics

A modified synthesis of methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate (halosulphuron) is described. The merits of the synthesis are (i) one pot chlorination of methyl 1-methyl-1 H-pyrazole-4-carboxylate (1) in presence of sulphuryl chloride resulting in methyl 3,5-dichloro-1-methyl-1 H-pyrazole-4-carboxylate (2) (ii) conversion of 3-chloro-5-mercapto-1-methyl-1 H-pyrazole-4-carboxylate (3) to 3-chloro-1-methyl-5-sulfamoyl pyrazole-4-carboxylate (4) under mild reaction conditions utilizing tetrabutyl ammonium chloride, N-chlorosuccinimide and ammonium carbonate (iii) condensation of sulphonamide (4) with carbamate (6) by microwave irradiation. Efforts were made to calculate, atom economy, reaction mass efficiency and E-factor for all the reaction steps involved in the synthesis of halosulfuron. The E-factor values in step 2 and step 4 reaction is lower, indicating that these reactions are greener (generation of less waste) when compared to the remaining steps in the synthesis.

Form of halosulfuron-methyl, a process for its preparation and use of the same

The present invention describes the crystalline form of halosulfuron-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.

Synthesis of Halosulfuron-methyl via Selective Chlorination at 3- and/or 5-Position of Pyrazole-4-carboxylates

Reactions of methyl pyrazole-4-carboxylates 4b-d with N-chlorosuccinimide under heating conditions without a solvent gave methyl 3,5-dichloro-1-methylpyrazole-4-carboxylate 4a in good yields. The reaction of 4a with sodium hydrosulfide led to a nucleophilic substitution on the 5-position regioselectively to afford methyl 3-chloro-1-methyl-5-mercaptopyrazole-4-carboxylate 6a, which was followed by oxidative chlorination and amination to obtain 3-chloro-1-methyl-5-sulfamoylpyrazole-4-carboxylate 2a. Finally, the reaction of 2a with phenyl 4,6-dimethoxypyrimidin-2-yl carbamate 7 provided methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4- carboxylate (halosulfuron-methyl) 1a promising herbicide in corn.