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Amidosulfuron

Amidosulfuron 95%TC
Amidosulfuron 75%WG

Herbicide
HRAC K3 WSSA 15; chloroacetamide

Amidosulfuron NOMENCLATURE
Common name amidosulfuron (BSI, pa E-ISO)
IUPAC name 1-(4,6-dimethoxypyrimidin-2-yl)-3-mesyl(methyl)sulfamoylurea
Chemical Abstracts name N-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-N-methylmethanesulfonamide
CAS RN [120923-37-7] Development codes AE F075032 (AgrEvo); Hoe 075032 (Hoechst)

Amidosulfuron PHYSICAL CHEMISTRY
Mol. wt. 369.4 M.f. C9H15N5O7S2 Form White, crystalline powder. M.p. 160-163 ºC V.p. 2.2 10-2 mPa (25 ºC) KOW logP = 1.63 (pH 2, 20 ºC) Henry 5.34  10-4 Pa m3 mol-1 (20 °C) S.g./density 1.5 Solubility In water 3.3 (pH 3), 9 (pH 5.8), 13 500 (pH 10) mg/l (20 ºC). In isopropanol 0.099, methanol 0.872, acetone 8.1 (all in g/l, 20 ºC). Stability Stable for 2 years at 25? ºC in unopened original containers. Abiotic hydrolysis, DT50 33.9 d (pH 5), 365 d (pH 7), 365 d (pH 9) (25 ºC). pKa 3.58

COMMERCIALISATION
Manufacturers Bayer CropScience

Amidosulfuron APPLICATIONS
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Acts by inhibiting biosynthesis of the essential amino acids valine and isoleucine, hence stopping cell division and plant growth. Selectivity derives from rapid metabolism in the crop. Metabolic basis of selectivity in sulfonylureas reviewed (M. K. Koeppe & H. M. Brown, Agro-Food-Industry, 6, 9-14 (1995)). Mode of action Selective, systemic herbicide, absorbed by the leaves and roots and translocated throughout the plant. Plant growth is inhibited, followed by the development of chlorotic patches which spread acropetally and then basipetally. Uses Post-emergence control of a wide range of broad-leaved weeds, especially cleavers, in winter wheat, durum wheat, barley, rye, triticale and oats, at 30-60 g/ha; controls docks in pasture. Formulation types WG. Selected products: 'Cleave' (Barclay); 'Gratil' (Bayer CropScience)