8947. Sulfentrazone

Nomenclature

CAS number: 122836-35-5
N-[2,4-Dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]phenyl]methanesulfonamide; 2′,4′-dichloro-5′-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)methanesulfonanilide; F-6285; FMC-97285; Authority (FMC).
C11H10Cl2F2N4O3S; mol wt 387.19.
C 34.12%, H 2.60%, Cl 18.31%, F 9.81%, N 14.47%, O 12.40%, S 8.28%.

Description and references

Aryltriazolinone herbicide; inhibits protoporphyrinogen oxidase in the chlorophyll biosynthetic pathway. Prepn: G. Theodoridis, US 4818275 (1989 to FMC); and structure-activity study: idem et al., ACS Symp. Ser. 504, 134 (1992). Metabolism and distribution in animals: L. Y. Leung et al., J. Agric. Food Chem. 39, 1509 (1991). Properties and field trials in soybeans: W. A. Van Saun et al., Brighton Crop Prot. Conf. - Weeds 1991, 77. Field trial in peanuts: W. C. Johnson, III, B. G. Mullinix, Jr., Peanut Sci. 21, 65 (1994).

Chemical structure

Properties

Tan solid, mp 75-78°. pKa 6.56. vapor pressure (25°): 1 × 109 mm Hg. Soly in water at 25° (mg/g): 0.11 (pH 6.0); 0.78 (pH 7.0); 16 (pH 7.5). LD50 orally in rats: 2855 mg/kg; dermally in rabbits: >2000 mg/kg; LC50 (96 hr) in bluegill sunfish, rainbow trout (ppm): 92.8, >130 (Van Saun).

Use

Herbicide.