4143. Flumioxazin

Nomenclature

CAS number: 103361-09-7
2-[7-Fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione; N-(7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxazin-6-yl)cyclohex-1-ene-1,2-dicarboximide; S-53482; V-53482; Sumisoya (Sumitomo); Valor (Valent).
C19H15FN2O4; mol wt 354.33.
C 64.40%, H 4.27%, F 5.36%, N 7.91%, O 18.06%.

Description and references

Selective postemergence herbicide that inhibits protoporphyrinogen oxidase. Prepn: E. Nagano et al., EP 170191; eidem, US 4640707 (1986, 1987 both to Sumitomo). Field study in peanut: S. D. Askew et al., Weed Technol. 13, 594 (1999). Metabolism in rat: Y. Tomigahara et al., J. Agric. Food Chem. 47, 305, 2429 (1999). Review of physical properties, mode of action, and field trials: R. Yoshida et al., Brighton Crop Prot. Conf. - Weeds 1991, 69-75.

Chemical structure

Properties

Yellowish brown, odorless, powder, mp 201.83-203.83°. Soly in water at 25°: 1.79 mg/l. Sol in common organic solvents. Vapor pressure at 22°: 2.41 × 106 mmHg. d20 1.5132 g/ml. LD50 in rats (mg/kg): >5000 orally; >2000 dermally. LC50 (4 hr) in rats (mg/m3): >3930 by inhalation. LC50 (96 hr) in bluegill, rainbow trout (mg/l): >21, 2.3 (Yoshida).

Use

Herbicide.