Structural Formula Vector Image
Title: Barban
CAS Registry Number: 101-27-9
CAS Name: (3-Chlorophenyl)carbamic acid 4-chloro-2-butynyl ester
Additional Names: m-chlorocarbanilic acid 4-chloro-2-butynyl ester; chloro-2-butynyl m-chlorocarbanilate; 4-chloro-2-butynyl N-(3-chlorophenyl)carbamate; barbamate; barbane; chlorinat
Manufacturers' Codes: CS-847
Trademarks: Carbyne (Spencer)
Molecular Formula: C11H9Cl2NO2
Molecular Weight: 258.10
Percent Composition: C 51.19%, H 3.51%, Cl 27.47%, N 5.43%, O 12.40%
Literature 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).
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).
Melting point: mp 75-76°
Toxicity data: 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.

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