2802. Dalapon

Nomenclature

CAS number: 75-99-0
2,2-Dichloropropanoic acid; α,α-dichloropropionic acid.
C3H4Cl2O2; mol wt 142.97.
C 25.20%, H 2.82%, Cl 49.60%, O 22.38%.

Description and references

Selective systemic herbicide for control of annual and perennial grasses. Prepn: GB 752761 (1956 to Dow); E. J. Kowolik, J. W. Fisher, GB 892584 (1962 to British Celanese); of free acid and sodium salt: Smeykal, Pallutz, Chem. Tech. (Leipzig) 15 (11), 654 (1963), C.A. 60, 6741c (1964). Acute toxicity: T. B. Gaines, R. E. Linder, Fundam. Appl. Toxicol. 7, 299 (1986). Toxicity data for the sodium salt: G. W. Bailey, J. L. White, Residue Rev. 10, 97 (1965). Quantitative NMR purity determn: R. J. Wells et al., J. Agric. Food Chem. 50, 3366 (2002).

Chemical structure

Properties

Liquid, bp20 98-99°. d20 1.4014. nD20 1.4551. LD50 in male, female rats (mg/kg): 7126, 6936 orally (Gaines, Linder).

Derivative

Sodium salt.

Nomenclature

CAS number: 127-20-8
Basfapon; Dowpon; Radapon.
C3H3Cl2NaO2; mol wt 164.95.
C 21.84%, H 1.83%, Cl 42.99%, Na 13.94%, O 19.40%.

Properties

Crystals, dec 174-176°. Soly in water at 25°, 45 g/100 ml; aq solns hydrolyze above 70°. Corrosive to iron.

Derivative

2-(2,4,5-Trichlorophenoxy)ethyl Ester.

Nomenclature

CAS number: 136-25-4
Erbon; Baron; Novon.
C11H9Cl5O3; mol wt 366.45.
C 36.05%, H 2.48%, Cl 48.37%, O 13.10%.

Description and references

Prepn: H. F. Brust, H. O. Senkbeil, US 2754324 (1956 to Dow).

Properties

Crystals, mp 49-50°. bp0.5 161-164°. d450 1.55. Sol in acetone, alc, kerosene, xylene. Insol in water. LD50 orally in rats: 1120 mg/kg (Bailey, White).

Caution

Potential symptoms of dalapon overexposure are irritation of eyes, skin, upper respiratory system; eye and skin burns; lassitude, loss of appetite, diarrhea, vomiting, slowing of pulse; CNS depression. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 100.

Use

Herbicide.