13-00962. Barban [Archived]

Nomenclature

CAS number: 101-27-9
(3-Chlorophenyl)carbamic acid 4-chloro-2-butynyl ester; m-chlorocarbanilic acid 4-chloro-2-butynyl ester; chloro-2-butynyl m-chlorocarbanilate; 4-chloro-2-butynyl N-(3-chlorophenyl)carbamate; barbamate; barbane; chlorinat; CS-847; Carbyne (Spencer).
C11H9Cl2NO2; mol wt 258.10.
C 51.19%, H 3.51%, Cl 27.47%, N 5.43%, O 12.40%.

Description and references

Prepn: Hopkins et al., J. Org. Chem. 24, 2040 (1959); US 2906614 (1959 to Spencer Chem.); Baskakov et al., Zh. Obshch. Khim. 33, 46 (1963). Activity as an herbicide: Hoffmann et al., Weeds 8, 198 (1960). Metabolism: Grunow et al., Food Cosmet. Toxicol. 8, 277 (1970). Toxicity study: Bailey, White, Residue Rev. 10, 97 (1965). Review: Abel, Rep. Prog. Appl. Chem. 47, 552 (1962).

Chemical structure

Properties

Crystals from n-hexane + benzene, mp 75-76°. Practically insol in water (soly at 25° = 11 ppm). Slightly sol in hexane; readily sol in benzene, ethylene dichloride. Hydrolyzed by alkali with liberation of the terminal chlorine. Hydrolysis under acidic conditions gives 3-chloroacrylic acid. LD50 orally in rats: 600 mg/kg (Bailey, White).

Caution

May cause skin irritation.

Use

Selective herbicide for wild oats.

Status

This monograph has been retired and is no longer subject to revision or update.