3045. Dichlone

Nomenclature

CAS number: 117-80-6
2,3-Dichloro-1,4-naphthalenedione; 2,3-dichloro-1,4-naphthoquinone; USR-604; Phygon; Phygon Paste; Phygon XL.
C10H4Cl2O2; mol wt 227.04.
C 52.90%, H 1.78%, Cl 31.23%, O 14.09%.

Description and references

Prepd by chlorination of 1,4-naphthoquinone: Bertheim, Ber. 34, 1554 (1901); Brass, K"ohler, Ber. 55, 2554 (1922); Sj"ostrand, US 2975196 (1961 to Svenska Oljeslageri Aktiebolaget); by oxidation of 2,3-dichloro-5,8-dihydro-1,4-naphthohydroquinone: Gaertner, US 2750427 (1956 to Monsanto); by oxidation of 2,3-dichloro-p-benzoquinone: Grinev et al., Zh. Obshch. Khim. 29, 90 (1959). Toxicity data: G. W. Bailey, J. L. White, Residue Rev. 10, 97 (1965). Review: Ter Horst, Ind. Eng. Chem. 35, 1255 (1943).

Chemical structure

Properties

Golden yellow needles or leaflets from alc, mp 193°. Sublimes. Practically insol in water (soly about 1 part in 10 million parts H2O). Soly in xylene and o-dichlorobenzene about 4%. Moderately sol in acetone, ether, benzene, dioxane. LD50 orally in rats: 1300 mg/kg (Bailey, White).

Caution

Irritating to skin, mucous membranes; CNS depressant: Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 318.

Use

Fungicide for agriculture and textiles; herbicide.