ChemicalBook--->CAS DataBase List--->100784-20-1

100784-20-1

100784-20-1 Structure

100784-20-1 Structure
IdentificationMore
[Name]

Halosulfuron methyl
[CAS]

100784-20-1
[Synonyms]

3-chloro-5-(((((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)-1-methyl-1h-pyrazole-4-carboxylic acid methyl ester
Battalion
BATTALION(R)
HALOSULFURON-METHYL
MANAGE(R)
Methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate
METHYL 5-([(4,6-DIMETHOXY-2-PYRIMIDINYL)AMINO]CARBONYLAMINOSULFONYL)-3-CHLORO-1-METHYL-1H-PYRAZOLE-4-CARBOXYLATE
mon 12000
NC-319
PERMIT
PERMIT(R)
SEMPRA(R)
1h-pyrazole-4-carboxylicacid,3-chloro-5-(((((4,6-dimethoxy-2-pyrimidinyl)amin
halosulfuron
Pyrazole-4-carboxylic acid, 3-chloro-5-(((((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)-1-methyl-, methyl ester
methyl ester 3-chloro-5-((((((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)sulfonyl)amino)sulfonyl)-1-methylpyrazole-4-carboxylic acid
HALOSULFURON-METHYL, 95%TC
HALOSULFURON-METHYL, 75%WDG
Halosulfuron methyl ,3-Chloro-5-(((((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)-1-methyl-1H-pyrazole-4-carboxylic acid methyl ester
1H-Pyrazole-4-carboxylic acid, 3-chloro-5-(4,6-dimethoxy-2-pyrimidinyl)aminocarbonylaminosulfonyl-1-methyl-, methyl ester
[EINECS(EC#)]

600-130-3
[Molecular Formula]

C13H15ClN6O7S
[MDL Number]

MFCD01631160
[Molecular Weight]

434.81
[MOL File]

100784-20-1.mol
Chemical PropertiesBack Directory
[Melting point ]

175-177°C
[density ]

1.618
[storage temp. ]

0-6°C
[solubility ]

Chloroform (Slightly), Methanol (Slightly, Heated)
[Water Solubility ]

Insoluble in water
[form ]

neat
[pka]

11.96±0.70(Predicted)
[color ]

White to Light yellow to Light orange
[Merck ]

14,4602
[Major Application]

agriculture
environmental
[InChI]

InChI=1S/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)
[InChIKey]

FMGZEUWROYGLAY-UHFFFAOYSA-N
[SMILES]

N1(C)C(S(NC(NC2=NC(OC)=CC(OC)=N2)=O)(=O)=O)=C(C(OC)=O)C(Cl)=N1
[CAS DataBase Reference]

100784-20-1(CAS DataBase Reference)
[EPA Substance Registry System]

100784-20-1(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

N
[Risk Statements ]

50/53
[Safety Statements ]

60-61
[RIDADR ]

UN3077 9/PG 3
[WGK Germany ]

3
[RTECS ]

UQ6392606
[HS Code ]

2935.90.9500
[HazardClass ]

9
[PackingGroup ]

III
[Storage Class]

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
[Hazard Classifications]

Aquatic Acute 1
Aquatic Chronic 1
Repr. 1B
[Toxicity]

LD50 orally in rats: 8865 mg/kg; dermally in rabbits: >2000 mg/kg; LC50 (4 hr) in rats: >4.3 mg/l (Suzuki)
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate(100784-20-1).msds
Hazard InformationBack Directory
[Hazard]

Moderately toxic by ingestion.
[Uses]

Herbicide.
[Definition]

ChEBI:Halosulfuron-methyl is a member of pyrazoles.
[Production Methods]

Halosulfuron-methyl is synthesised through a multi-step process that builds its sulfonylurea herbicidal structure. The synthesis typically begins with 3-chloro-1-methylpyrazole-5-hydroxy-4-methyl formate as the starting material, which undergoes condensation with dimethylaminothioformyl chloride to form a thioformyloxy intermediate. This is followed by a rearrangement reaction to yield a dimethylaminothioyl derivative. The next step involves chlorosulfonation, introducing a sulfonyl chloride group at the pyrazole ring. This intermediate is then subjected to ammoniation, converting the sulfonyl chloride into a sulfonamide. Finally, the sulfonamide is coupled with a pyrimidine derivative, such as 4,6-dimethoxypyrimidine-2-amine, through a carbamoylation reaction, and the resulting compound is methylated to produce the active halosulfuron-methyl ester.
[Mechanism of action]

Systemic, selective, acts by inhibiting biosynthesis of essential amino acids valine and isoleucine restricting plant growth. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS
[Pesticide Type]

Herbicide
Spectrum DetailBack Directory
[Spectrum Detail]

Halosulfuron methyl(100784-20-1)1HNMR
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