Flufenacet

Title: Flufenacet
CAS Registry Number: 142459-58-3
CAS Name: N-(4-Fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide
Additional Names: N-isopropyl-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-(4¢-fluorooxyacetanilide)
Manufacturers' Codes: BAY FOE-5043; FOE-5043
Trademarks: Define (Bayer CropSci.)
Molecular Formula: C14H13F4N3O2S
Molecular Weight: 363.33
Percent Composition: C 46.28%, H 3.61%, F 20.92%, N 11.57%, O 8.81%, S 8.83%
Literature References: Oxyacetamide herbicide. Prepn: H. Förster et al., DE 3821600; eidem, US 4968342 (1989, 1990 both to Bayer). Ecotoxicological profile: T. Hall, Pflanzenschutz-Nachr. Bayer (Engl. Ed.) 50, 187 (1997). Series of articles on chemical and biological properties, determn and field trials: ibid. 105-236. Review of properties and grass control in crops: R. Deege et al., Brighton Crop Prot. Conf. - Weeds 1995, 43.
Properties: White to tan solid, mp 75-77°. Does not dissociate. Soly in water at 25° (mg/l): 56 pH 4; 56 pH 7; 54 pH 9. Log P (octanol/water): 3.2. Vapor pressure at 20°: 9.0 ´ 10-5 Pa. LD50 in rats (mg/kg): 589-1617 orally; >2000 dermally. LD50 orally in mice, bobwhite quail, mallard duck: 1331-1756, 1608, >2000 mg/kg. LC50 in sunfish, rainbow trout, sheepshead minnow: 2.1-2.4, 3.5-5.8, 3.3 mg/l (Hall).
Melting point: mp 75-77°
Log P: Log P (octanol/water): 3.2
Toxicity data: LD50 in rats (mg/kg): 589-1617 orally; >2000 dermally; LD50 orally in mice, bobwhite quail, mallard duck: 1331-1756, 1608, >2000 mg/kg; LC50 in sunfish, rainbow trout, sheepshead minnow: 2.1-2.4, 3.5-5.8, 3.3 mg/l (Hall)
Use: Pre-emergent herbicide.
Flufenamic Acid Flufenoxuron Fluindione Flumazenil Flumecinol

Flufenacet is an oxyacetanilide herbicide applied before crops have emerged.[1][2]

In the model plant Arabidopsis thaliana it causes similar symptoms to the fiddlehead mutant.[3]