5595. Lufenuron

Nomenclature

CAS number: 103055-07-8
N-[[[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]amino]carbonyl]-2,6-difluorobenzamide; 1-[2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-3-(2,6-difluorobenzoyl)urea; fluphenacur; CGA-184699; Program (Novartis).
C17H8Cl2F8N2O3; mol wt 511.15.
C 39.95%, H 1.58%, Cl 13.87%, F 29.73%, N 5.48%, O 9.39%.

Description and references

Chitin synthesis inhibitor. Prepn: J. Drabek, M. Bger, EP 179022; eidem, US 4798837 (1986, 1989 both to Ciba-Geigy). Effect on fleas following oral administration in cats: W. F. Hink et al., J. Med. Entomol. 28, 424 (1991). HPLC determn: M. Zakson et al., Pestic. Sci. 35, 117 (1992). Review of properties and field trials in crops: F. Buholzer et al., Meded. Fac. Landbouwwet. Univ. Gent 57, 781-790 (1992).

Chemical structure

Properties

Colorless, odorless, crystalline solid, mp 174.1°. Vapor pressure (25°): <4 × 106 Pa. Soly (20°): water <0.1 ppm; acetone 40%; cyclohexanone 35%; xylene 5%; methanol 4.5%. Log P (n-octanol/water): 5.12. LD50 in rats (mg/kg): >2000 orally; LC50 in rats (mg/m3): >2350 (Buholzer).

Therapeutic Category (Veterinary)

Ectoparasiticide.