Thifensulfuron methyl

English Synonyms: HARMONY; METHYL 3- [METHYL 3- (4-METHOXY-6-METHYL-1,3,5-TRIAZIN-2-YL-CARBAMOYLSULFAMOYL) -THIOPHEN-2-CARBOXYLATE; PINNACLE; PINNACLE (TM); THIFENSULFURON- METHYL; 2-thiophenecarboxylic acid, (4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino); dpx-m6316

CAS number: 79277-27-3

Molecular formula: C12H13N5O6S2

Molecular weight: 387.39

EINECS number:

Related categories: H; HA-HTPesticides & Metabolites; H-MAlphabetic; Alpha sort; Herbicides; Pesticides & Metabolites; Q-ZAlphabetic; TF - TOPesticides & Metabolites; Urea structure; Herbicides; Urea Herbicides; Pesticides; APIs; Analytical Standards; Pesticides; Pesticide residues, veterinary drugs and chemical fertilizers

Mol file: 79277-27-3.mol

Thiophene Huanglong

Thiophene Huang Long Nature

Melting point 176 ° C

Storage conditions 0-6 ° C

Acidity coefficient (pKa) pKa at 25 °: 4.0

Merck 13,9387

CAS Database 79277-27-3 (CAS DataBase Reference)

2-Thiophenecarboxylic acid, 3 - [[(4-methoxy-6-methyl- 1,3,5-triazin-2-yl) amino] carbonyl] amino] sulfonyl] -27-3)

Thiophene Huanglong Uses and methods of synthesis

Toxic rats acute oral LD50> 5000mg / kg, rabbits acute percutaneous LD50> 2000mg / kg. Mild irritation to the eyes. 2-year rat feeding trial no effect dose of 25mg / kg. No effect of second generation breeding dose of 2500mg / kg. No teratogenic and mutagenic effects were observed under the experimental conditions. Rainbow trout, sunfish LC50> 100mg / L (96h). Mallard LD50> 2510mg / kg. Bee LD50> 12.5 μg / bird.

Pure chemical nature of white crystals. m.p. 186 ° C, relative density 1.49, vapor pressure 3.6x10-4 Pa (25 ° C). Solubility in organic solvents: methylene chloride 27.5 g / L, acetone 11.9 g / L, acetonitrile 7.3 g / L, ethyl acetate 2.6 g / L, methanol 2.6 g / L, ethanol 0.9 g / L, 0.2 g / L, hexane <0.1 g / L; solubility in water: 24 mg / L at pH 4, 260 mg / L at pH 5 and 2400 mg / L at pH 6. The partition coefficients are 3.3 (pH = 5) and 0.027 (pH = 7). <55 ℃ stable, light is stable. The half-lives of hydrolysis reaction at 45 ℃ were 4.7h (pH = 3), 38h (pH = 5), 250h (pH = 7) and 11 h (pH = 9).

Use Thiosulfuron is an intrinsically conductive post-emergence selective herbicide that is a branched-chain amino acid synthesis inhibitor that inhibits the biosynthesis of valine, leucine and isoleucine, prevents cell division and stops sensitive crops Grow. Mainly used for the control of cereal crops, wheat, barley, oats, corn field broadleaf weeds, such as Amaranthus retroflexus, purslane, sowing Artemisia annua, shepherd's purse, Salsola, Galium aparine, And so on, Cactus, field Convolvulus and grass invalid. Wheat, barley 2 leaf stage to booting, weeds out to 2 to 4 leaf stage, with 75% of the suspension 0.25 ~ 0.41g / 100m2, water 4.5kg, 0.2% by volume of liquid non-ionic surfactant , Stems and leaves spray treatment.

Production method Preparation of 3-amino-2-carboxymethyl thiophene Acrylonitrile in DMF presence, at 10 ~ 12 ℃ chlorine reaction 6 ~ 7h, 2,3-dichloropropanenitrile; thioglycolic acid in the presence of concentrated sulfuric acid , And anhydrous methanol at room temperature for 8h, methyl mercaptoacetate.

The methyl mercaptoacetate, anhydrous methanol and sodium methoxide were cooled to 10 ~ 15 ° C, dichloropropionitrile and anhydrous methanol solution was added dropwise, the reaction was continued at 10 ~ 15 ° C for 5h, the methanol was distilled off under reduced pressure, the residue After cooling, add ice water, filtered, the product yield 55%, mp 58 ~ 61 ℃.

Preparation of 2-hydroxymethyl-3-sulfonyl chloride thiophene Glacial acetic acid and a little hydrochloric acid into the sulfur dioxide under cooling, set aside for use in the ice bath.

The 3-amino-2-carboxymethyl thiophene at 0 ~ 5 ° C was added to the hydrochloric acid, glacial acetic acid mixture, stirring, the aqueous sodium nitrite solution was slowly dropped to continue the reaction 30min, at 0 ° C to be used sulfur dioxide The solution was added, and a little cuprous chloride was added to control the temperature to naturally rise to 25-30 ° C for 10 hours. The reaction solution was poured into ice water, filtered, washed and dried. The yield was 75.7%. Mp 66-68 ° C.

Preparation of 2-Carboxymethyl-3-sulfonylaminothiophene The resulting sulfonylchloride thiophene was dissolved in dichloroethane, cooled to 5 ° C and ammonia gas was purged. Ammonia hydrolyzate was filtered and the filtrate was concentrated to give the product in 95% yield, m.p. 110-114 ° C.

Synthesis of thifensulfuron The reaction of 2-carboxymethyl-3-sulfonylaminothiophene with 3-methoxy-5-methyltriazine isocyanate gave thiazoneon.

Category Pesticides

Toxicity classification of low toxicity

Acute Toxicity Oral - Rat LD50:> 5000 mg / kg

Flammability Hazard Characteristics Combustion produces toxic nitrogen oxides and sulfur oxides gases

Storage and transportation warehouse ventilation low temperature drying; separate storage and transportation of food raw materials

Extinguishing agent dry powder, foam, sand