| Identification | More | [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 Properties | Back 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 Data | Back 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) |
| Hazard Information | Back 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 |
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