3931. Famoxadone

Nomenclature

CAS number: 131807-57-3
5-Methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-2,4-oxazolidinedione; 3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione; DPX-JE874; Famoxate (DuPont).
C22H18N2O4; mol wt 374.39.
C 70.58%, H 4.85%, N 7.48%, O 17.09%.

Description and references

Inhibits electron transport via blockage of ubiquinol:cytochrome c oxidoreductase. Prepd not claimed: D. Geffken, D. R. Rayner, US 4957933 (1990 to DuPont). Biological activity and field trials: M. M. Joshi, J. A. Sternberg, Proc. Br. Crop Prot. Conf. - Pests Dis. 1996, 21. Mode of action: D. B. Jordan et al., Pestic. Sci. 55, 105 (1999). Environmental fate: K. M. Jernberg, P. W. Lee, ibid. 587. Metabolic fate in plants and animals: P. W. Lee et al., ibid. 589. Review of synthesis and structure-activity relationship: J. A. Sternberg et al., ACS Symp. Ser. 686, 216-227 (1998).

Chemical structure

Properties

mp 140.3-141.8°. Log P (n-octanol/water): 4.65 (pH 7). Soly in water: 52 μg/L. LD50 in rats (mg/kg): >5000 orally; >2000 dermally (Joshi, Sternberg).

Use

Agricultural fungicide.