4195. Flupyrsulfuron-methyl

Nomenclature

CAS number: 144740-53-4
2-[[[[(4,6-Dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-6-(trifluoromethyl)-3-pyridinecarboxylic acid methyl ester; methyl 2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-6-(trifluoromethyl)nicotinate.
C15H14F3N5O7S; mol wt 465.36.
C 38.71%, H 3.03%, F 12.25%, N 15.05%, O 24.07%, S 6.89%.

Description and references

Sulfonylurea postemergent herbicide which inhibits acetolactate synthetase. Prepn: T. A. Andrea, P. H. T. Liang, EP 502740; eidem, US 5393734 (1992, 1995 both to Du Pont). Description of chemical and biological activities: S. R. Teaney et al., Brighton Crop Prot. Conf. - Weeds 1995, 49. Metabolism and selectivity: M. K. Koeppe et al., Pestic. Biochem. Physiol. 59, 105 (1998). LC determn in soil and water: C. R. Powley, P. A. de Bernard, J. Agric. Food Chem. 46, 514 (1998). Environmental fate: S. K. Singles et al., Pestic. Sci. 55, 288 (1999).

Chemical structure

Properties

Solid, mp 130-137°.

Derivative

Sodium salt.

Nomenclature

CAS number: 144740-54-5
DPX-KE459; Lexus (DuPont); Millenium (DuPont).
C15H13F3N5NaO7S; mol wt 487.34.
C 36.97%, H 2.69%, F 11.70%, N 14.37%, Na 4.72%, O 22.98%, S 6.58%.

Properties

Solid, mp 172-173°. Most stable in aqueous solutions, pH 5-7; stable in most organic solvents including methanol, acetonitrile, acetone, ethyl acetate and methylene chloride. Soly in water at 25° (ppm): 62.7 (pH 5); 603 (pH 7). pKa: 4.9. LD50 in rats, Japanese quail, mallard duck (mg/kg): >5000, >2250, >2250 orally; in rabbits (mg/kg): >2000 dermally. LC50 (96hr) in rainbow trout, carp (mg/l): 470, 820; LC50 in rats (mg/l): >5.8 by inhalation (Teaney).

Use

Herbicide.