4009. Fenuron

Nomenclature

CAS number: 101-42-8
N,N-Dimethyl-N′-phenylurea; N-phenyl-N′,N′-dimethylurea; Dybar (DuPont).
C9H12N2O; mol wt 164.20.
C 65.83%, H 7.37%, N 17.06%, O 9.74%.

Description and references

Prepn: Crosby, Niemann, J. Am. Chem. Soc. 76, 4458 (1954); Gilbert, Sorma, US 2729677 (1956 to Allied Chem.); Jones, US 2768971 (1956 to ICI); Applegath et al., US 2857430 (1958 to Monsanto). Prepn of trichloroacetate: E. E. Gilbert et al., US 2782112 (1957 to Allied Chem.). Toxicity data: G. W. Bailey, J. L. White, Residue Rev. 10, 97 (1965).

Chemical structure

Properties

Crystals, mp 131-133°. Sparingly sol in water (0.29% at 24°); in hydrocarbons. LD50 orally in rats: 7500 mg/kg (Bailey, White).

Derivative

Trichloroacetate.

Nomenclature

CAS number: 4482-55-7
Fenuron TCA; Urab (Hopkins).
C11H13Cl3N2O3; mol wt 327.59.
C 40.33%, H 4.00%, Cl 32.47%, N 8.55%, O 14.65%.

Properties

mp 65-68°. Esp effective in woody plant control.

Caution

If hydrolyzed to aniline can cause methemoglobinemia: Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 331.

Use

Herbicide.