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Sulfosulfuron

Sulfosulfuron 95%TC
Sulfosulfuron 75%WG

Herbicide
HRAC B WSSA 2; sulfonylurea

Sulfosulfuron NOMENCLATURE
Common name sulfosulfuron (BSI, pa ISO)
IUPAC name 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea
Chemical Abstracts name N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-2-(ethylsulfonyl)imidazo[1,2-a]pyridine-3-sulfonamide
CAS RN [141776-32-1] Development codes MON 37500 (Monsanto); TKM 19; MON 37588 (Monsanto) (for WG formulation)

Sulfosulfuron PHYSICAL CHEMISTRY
Mol. wt. 470.48 M.f. C16H18N6O7S2 Form White, odourless solid. M.p. 201.1-201.7 °C V.p. 8.81  10-8 mPa (25 °C) KOW logP <1 (pH 5, 9) Henry 8.15  10-7 (pH 5), 8.83  10-9 (pH 7), 2.97  10-8 (pH 9) (calc.) S.g./density 1.5185 (20 °C) Solubility In water 17.6 (pH 5), 1627 (pH 7), 482 (pH 9) (all mg/l, 20 °C). In acetone 0.71, methanol 0.33, ethyl acetate 1.01, dichloromethane 4.35, xylene 0.16, heptane <0.01 (all g/l, 20 °C). Stability Stable <54 °C for 14 d. pKa 3.51 (20 °C)

COMMERCIALISATION
History Discovered by Takeda Chemical Industries, Ltd (now Sumitomo Chemical Takeda Agro Company Ltd). Reported by S. K. Parrish et al. (Proc. Br. Crop Prot. Conf. - Weeds, 1995, 1, 57). Developed jointly by Monsanto Co. and Takeda and introduced in 1997. Manufacturers Sumitomo Chemical Takeda

Sulfosulfuron 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 Systemic herbicide, absorbed by the root system and/or leaf surface, and translocated to symplast and apoplast. Uses Has demonstrated activity for the control of annual broad-leaved weeds and grass weeds in cereals (wheat), at 10-35 g/ha. Phytotoxicity Barley and oats are sensitive. Tolerance of durum wheat is variety-specific. Formulation types WG. Compatibility Not compatible with fertiliser solutions with pH 5, nor with non-ionic surfactants or other additives that alter the pH of the spray solution below pH 5. Not compatible with malathion. Crop injury may result if applied within 60 days of crop emergence where an organophosphate insecticide has been applied as an in-furrow treatment. Selected products: 'Maverick' (wheat) (Monsanto); 'Monitor' (wheat) (Monsanto); 'Outrider' (non-crop land) (Monsanto)