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Thifensulfuorn-methyl

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NOMENCLATURE

Common name thifensulfuron-methyl 
IUPAC name methyl 3-(4-methoxy-6-methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)thiophen-2-carboxylate
Chemical Abstracts name methyl 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylate
 CAS RN [79277–27–3] 
PHYSICAL CHEMISTRY
Composition Tech. is >96%. Mol. wt. 387.4 M.f. C12H13N5O6S2 Form Off-white solid, with no odour. M.p. 176 °C; (tech., 171.1 °C) V.p. 1.7 × 10-5 mPa (25 °C) (Knudsen method) Kow logP = 1.06 (pH 5), 0.02 (pH 7), 0.0079 (pH 9) Henry 9.7 × 10-10 Pa m3 mol-1 (pH 7, 25 °C) S.g./density 1.580 (20 °C) Solubility In water 223 (pH 5), 2240 (pH 7), 8830 (pH 9) (all in mg/l, 25 °C). In hexane <0.1, o-xylene 0.212, ethyl acetate 3.3, methanol 2.8, acetonitrile 7.7, acetone 10.3, dichloromethane 23.8 (all in g/l, 25 °C). Stability Aqueous hydrolysis DT50 4–6 d (pH 5), 180 d (pH 7), 90 d (pH 9) (all 25 °C). pKa 4.0 (25 °C)
 
APPLICATIONS
Biochemistry Affects sensitive weeds through inhibition of the enzyme acetolactate synthase (ALS). Inhibition of ALS leads to the rapid cessation of cell division and subsequent growth processes in plants. Mode of action Post-emergence selective herbicide, acting primarily through foliar uptake, with little or no soil activity. Uses Selective control of a wide range of annual weeds in cereals, maize and pasture. Phytotoxicity Treated cereals may experience a temporary inhibition of growth and colour changes in the leaves, but these have no ultimate effect on the yield. Formulation types SG; TB; WG.  
ENVIRONMENTAL FATE
Animals In mammals, following oral administration of thifensulfuron-methyl, 70–75% of the unchanged material is excreted in the urine and faeces. The primary degradation mechanism involves hydrolysis of the methoxycarbonyl group, O-demethylation of the heterocyclic ring, and hydrolysis of the sulfonylurea group. Plants In field-grown wheat and corn, residues dissipate rapidly, involving cleavage of the urea bridge and metabolism of the methoxy group on the triazine ring, and hydrolysis of the methyl ester group on the thiophene ring. Soil/Environment Thifensulfuron-methyl degrades rapidly in soil by microbial degradation, chemical hydrolysis and photoylsis; DT50 <1 to 7 d, DT90 <1 to 50 d.
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >2000 mg/kg. Non-irritating to skin or eyes. Not a skin sensitiser. Inhalation LC50 (4 h) for rats >7.9 mg/l air. NOEL NOAEL (90 d) for rats 100 mg/kg diet; (2 y) for rats 500 mg/kg diet. NOAEL in reproduction (2-generation) study in rats 2500 mg/kg diet; in teratogenicity study in rats 200 mg/kg daily. ADI (EC) 0.01 mg/kg b.w. [2001]; (EPA) cRfD 0.013 mg/kg b.w. [1991]; (company assignment) 0.026 mg/kg. Other Non-mutagenic in the Ames and three other mutagenicity tests. Toxicity class WHO (a.i.) U EPA (formulation) IV (SG, TB, WG) EC classification N; R50, R53 
ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >2510 mg/kg. Dietary LC50 (8 d) for mallard ducks and Japanese quail >5620 mg/kg diet. Fish LC50 (96 h) for rainbow trout 100, bluegill sunfish 520 mg/l. Daphnia LC50 (48 h) 470 mg/l. Algae NOEC (120 h) for green algae 15.7 mg/l. Other aquatic spp. EC50 (14 d) for Lemna gibba 0.0016 mg/l. Bees Non-toxic to bees. LD50 (48 h, topical) >12.5 μg/bee. Worms LC50 >2000 mg/kg. Other beneficial spp. LR50 for Aphidius rhopalosiphi and Typhlodromus pyri >82 g product/ha