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| | Thifensulfuron methyl Basic information |
| | Thifensulfuron methyl Chemical Properties |
| Melting point | 176°C | | density | 1.560±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | Water Solubility | Practically insoluble in water | | solubility | DMSO (Slightly, Heated), Methanol (Slightly, Heated) | | form | Solid | | pka | pKa at 25°: 4.0 | | color | White to Almost white | | λmax | 280nm(Acidic aq.)(lit.) | | Merck | 14,9316 | | BRN | 7448062 | | Henry's Law Constant | 3.4×108 mol/(m3Pa) at 25℃, HSDB (2015) | | Major Application | agriculture
environmental | | InChI | 1S/C12H13N5O6S2/c1-6-13-10(16-12(14-6)23-3)15-11(19)17-25(20,21)7-4-5-24-8(7)9(18)22-2/h4-5H,1-3H3,(H2,13,14,15,16,17,19) | | InChIKey | AHTPATJNIAFOLR-UHFFFAOYSA-N | | SMILES | COC(=O)c1sccc1S(=O)(=O)NC(=O)Nc2nc(C)nc(OC)n2 | | LogP | 1.560 | | CAS DataBase Reference | 79277-27-3(CAS DataBase Reference) | | EPA Substance Registry System | Thifensulfuron-methyl (79277-27-3) |
| Hazard Codes | N | | Risk Statements | 50/53 | | Safety Statements | 60-61 | | RIDADR | UN3077 9/PG 3 | | WGK Germany | 2 | | RTECS | XM8463000 | | HazardClass | 9 | | PackingGroup | III | | HS Code | 29350090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Acute 1
Aquatic Chronic 1 | | Hazardous Substances Data | 79277-27-3(Hazardous Substances Data) | | Toxicity | LC50 (96-hour) for both bluegill sunsh and rainbow trout >100 mg/L; LC50
(48-hour) for Daphnia magna >1,000 mg/L (Humburg et al., 1989); acute oral LD50 for
rats >5,000 mg/kg (Hartley and Kidd, 1987). |
| | Thifensulfuron methyl Usage And Synthesis |
| Uses | Herbicide. | | Uses | Postemergence herbicide used to control wild garlic and many broad-leaved weeds
in barley and spring wheat. | | Definition | ChEBI: A methyl ester resulting from the formal condensation of the carboxy group of thifensulfuron with methanol. It is used as a post-emergence herbicide for the control of grass and broad-leaved weeds. | | Production Methods | The production of thifensulfuron-methyl, a sulfonylurea herbicide, involves a multi-step chemical synthesis starting with the construction of a substituted benzene sulfonamide and a triazine ring system. These components are coupled through a sulfonylurea linkage to form the active molecule. The process typically includes steps such as chlorination, amination, and methylation, followed by purification and crystallization to achieve high purity. | | Agricultural Uses | Herbicide: A herbicide for postemergence broadleaf weed control
in crops for food such as soybeans and cotton. Not
listed for use in EU countries. | | Trade name | ALLY®; BASIS® (rimsulfuron + thifensulfuron
methyl); CANVAS® (thifensulfuron methyl + tribenuron
methyl + metsulfuron-methyl); DPX-M6316®;
EXPRESS®; HARMONY® Extra (thifensulfuron
methyl + tribenuron methyl); INM-6316®; PINNACLE®;
PROSPECT®; RELIANCE® SYNCHRONY®, (chlorimuron-
ethyl + thifensulfuron methyl) | | Mechanism of action | Selective, absorbed through foliage, inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS | | Environmental Fate | Chemical/Physical. May hydrolyze in aqueous solutions forming methyl alcohol and
3-(((((4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)-2-
thiophenecarboxylic acid. | | Metabolic pathway | The hydrolytic degradation of thifensulfuron methyl is
pH dependent and, in alkaline condition, specifically
yields the corresponding free acid. Primary
degradation cleaves the sulfonylurea moiety to give
two typical hydrolyzed products, sulfonamide and
aminotriazine analogs, derived from thifensulfuron
methyl in acidic and neutral conditions. Hydrolysis of
the ester linkage proceeds in mammals, plants, soils, and also chemical hydrolysis, and opening of the
triazine ring occurs to yield the acetyltriuret analog
identified. On the other hand, by hydrolysis, O-
demethylated thifensulfuron methyl undergoes opening
of the triazine ring to give the corresponding
acetyltriuret analog. Under photolytic conditions,
methyl 3-(4-methoxy-6-methyl-1,3,5-triazin-2-
yl)aminothiophene-2-carboxylate is identified. | | Pesticide Type | Herbicide |
| | Thifensulfuron methyl Preparation Products And Raw materials |
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