4184. Fluoxastrobin

Nomenclature

CAS number: 361377-29-9
(1E)-[2-[[6-(2-Chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy]phenyl](5,6-dihydro-1,4,2-dioxazin-3-yl)methanone O-methyloxime; HEC-5725; Fandango (Bayer CropSci.).
C21H16ClFN4O5; mol wt 458.83.
C 54.97%, H 3.51%, Cl 7.73%, F 4.14%, N 12.21%, O 17.43%.

Description and references

Leaf-systemic broad-spectrum fungicide for use in cereal and food crops; member of methoxyimiodihydro-dioxazines. Prepn (stereochem. unspecified): U. Heinemann et al., DE 19602095; eidem, US 6103717 (1997, 2000 both to Bayer). Comprehensive description: S. Dutzmann et al., BCPC Conf. - Pests Dis. 2002, 365. Field trial in winter wheat seeds: I. Haeuser-Hahn et al., BCPC Int. Congr. - Crop Sci. Technol. 2003, 801. Series of articles on chemistry, biology, determn, and environmental fate: Pflanzenschutz-Nachr. Bayer (Engl. Ed.) 57, 299-449 (2004). Ecotoxicology: P. Breuer, ibid. 319.

Chemical structure

Properties

White crystals with slight characteristic odor, mp 103-108°. bp 497° (est.). d420 1.422. Log P (octanol/water): 2.86 (20°). Vapor pressure at 20° (extrapolated): 6 × 10-10 Pa. Soly at 20° (g/l): n-heptane 0.04; 2-propanol 6.7; xylene 38.1; dichloromethane >250; in water (mg/l): 2.56 (unbuffered); 2.43 (pH 4); 2.29 (pH 7); 2.27 (pH 9). LD50 in rats, bobwhite quail (mg/kg): >2500, >2000 orally; LC50 (96 hr) rainbow trout, bluegill sunfish, carp (mg/l): 0.44, 0.97, 0.57 (Breuer).

Use

Agricultural fungicide.