3142. Diflubenzuron

Nomenclature

CAS number: 35367-38-5
N-[[(4-Chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide; 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea; difluron; DU-112307; PH-60-40; TH-6040; ENT-29054; OMS-1804; Dimilin (Duphar); Duphacid (Duphar); Micromite (Uniroyal).
C14H9ClF2N2O2; mol wt 310.68.
C 54.12%, H 2.92%, Cl 11.41%, F 12.23%, N 9.02%, O 10.30%.

Description and references

Substituted benzoylphenylurea, inhibits chitin deposition in insect cuticle. Prepn: K. Wellinga, R. Mulder, DE 2123236; eidem, US 3748356 (1971, 1973 both to Philips). Insecticidal activity: K. Wellinga et al., J. Agric. Food Chem. 21, 993 (1973); R. Mulder, M. J. Gijswijt, Pestic. Sci. 4, 737 (1973). Mode of action: E. Hunter, J. F. V. Vincent, Experientia 30, 1432 (1974); S. M. Meola, R. T. Mayer, Science 207, 985 (1980). Field trials against locusts and grasshoppers: A. Bouaichi et al., Crop Prot. 13, 53, 60 (1994). Brief review: J. L. Marx, Science 197, 1170-1172 (1977). Review of activity, environmental fate, mode of action: A. Verloop, C. D. Ferrell, ACS Symp. Ser. 37, 237-270 (1977); of chemistry and analyses: B. Rabenort et al., Anal. Methods Pestic. Plant Growth Regul. 10, 57-72 (1978).

Chemical structure

Properties

White to yellowish brown crystalline solid, mp 210-230° (technical grade); mp 239° (pure compd). Soly in water 0.2 ppm at 20°. Moderate to good soly in polar to very polar solvents; e.g. acetone 0.65 gm/100 ml at 20°. Partition coefficient (dichloromethane): 50 (pH 5.6); (1-octanol/water): ≈5000. LD50 in mice, rats (formulation with 50% kaolin) (g/kg): 4.64, >10 orally (Mulder, Gijswijt).

Use

Insecticide.