| Identification | More | [Name]
Triflusulfuron-methyl | [CAS]
126535-15-7 | [Synonyms]
DEBUT
METHYL 2-[4-(DIMETHYLAMINO)-6-(2,2,2-TRIFLUOROETHOXY)-1,3,5-TRIAZIN-2-YLAMINOCARBONYLAMINOSULFONYL]-3-METHYLBENZOATE
SAFARI
TRIFLUSULFURON-METHYL
UPBEET
Triflulsulfuron-methyl
Dubur
methyl 2-((4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)carbamkoylaulfamoyl)-m-methylbenzaote
methyl-2-(((4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)carbonoylaminosulfonyl)-3-methylbensoate
Upbeat
TRIFLUSULPHURONMETHYL
Methyl 2-[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylaminocarbonylaminosulfonyl]-3-methylbenzoate
DPX 66037
methyl-2-[4-dimethylamino-6-(2,2,2-trifluo-roethoxy)-1,3,5-triazin-2-yl] carbamoylsulfamoyl-m-methyl benzoate
Benzoic acid, 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methyl-, methyl ester | [EINECS(EC#)]
603-146-9 | [Molecular Formula]
C17H19F3N6O6S | [MDL Number]
MFCD03095701 | [Molecular Weight]
492.43 | [MOL File]
126535-15-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
160-163° | [density ]
1.493±0.06 g/cm3(Predicted) | [Fp ]
150 °C | [storage temp. ]
0-6°C | [form ]
neat | [pka]
4.4(at 25℃) | [BRN ]
8171352 | [Henry's Law Constant]
4.2×102 mol/(m3Pa) at 25℃, Maniere et al. (2011) | [Major Application]
agriculture
environmental | [InChI]
InChI=1S/C17H19F3N6O6S/c1-9-6-5-7-10(12(27)31-4)11(9)33(29,30)25-15(28)22-13-21-14(26(2)3)24-16(23-13)32-8-17(18,19)20/h5-7H,8H2,1-4H3,(H2,21,22,23,24,25,28) | [InChIKey]
IMEVJVISCHQJRM-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC=CC(C)=C1S(NC(NC1=NC(N(C)C)=NC(OCC(F)(F)F)=N1)=O)(=O)=O | [CAS DataBase Reference]
126535-15-7(CAS DataBase Reference) | [EPA Substance Registry System]
126535-15-7(EPA Substance) |
| Safety Data | Back Directory | [WGK Germany ]
1 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
Carc. 2 | [Toxicity]
LD50 orally in rats: >5000 mg/kg; dermally in rabbits: >2000 mg/kg (Peeples) |
| Hazard Information | Back Directory | [Description]
Triflusulfuron-methyl is a s ulfonylurea herbicide. It is moderately soluble in water and has a low volatility. It is not expected to be persistent in soil systems but may be persistent in water depending on local conditions. It is not expected to leach to groundwater. Whilst its toxicity to aquatic plants is high, toxicity to most other species is moderate to low. Triflusulfuron-methyl has a low oral mammalian toxicity and is thought to be a respiratory tract irritant. It is possible that this substance is carcinogenic. | [Chemical Properties]
This product has an mp of 160-163°C and a dissociation constant (pKa) of 4.4. Its solubility in water at 25°C is 1 mg/L (pH=3), 3 mg/L (pH=5), 110 mg/L (pH=7), and 11,000 mg/L (pH=9). Its partition coefficient is 9.2. Its half-life in water at 25°C is 3.7 days (pH=5), 32 days (pH=7), and 36 days (pH=9). It degrades rapidly in soil, primarily through microbial degradation under alkaline conditions and chemical hydrolysis under neutral and acidic conditions. Under laboratory conditions, its half-life in soil is 3-6 days. | [Uses]
Herbicide. | [Definition]
ChEBI: Triflusulfuron-methyl is a methyl ester resulting from the formal condensation of the carboxy group of triflusulfuron with methanol. A proherbicide for triflusulfuron. It has a role as a proherbicide, an agrochemical and an EC 2.2.1.6 (acetolactate synthase) inhibitor. It is a benzoate ester, a methyl ester, a N-sulfonylurea, a member of 1,3,5-triazines, a tertiary amino compound, an aromatic ether and an organofluorine compound. It is functionally related to a triflusulfuron. | [Production Methods]
In industrial settings, the synthesis of triflusulfuron-methyl begins with the preparation of a triazine ring system, typically derived from cyanuric chloride, which undergoes sequential substitution with fluorinated aromatic amines and methoxy groups. This intermediate is then reacted with a sulfonyl isocyanate or sulfonamide to form the characteristic sulfonylurea bridge, a key functional group responsible for herbicidal activity. The process requires precise control of temperature, solvent conditions, and pH to ensure high purity and yield. | [Mechanism of action]
Inhibits acetolactate synthase (ALS), an enzyme essential for amino acid synthesis in plants | [Pesticide Type]
Herbicide |
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