1772. Captan

Nomenclature

CAS number: 133-06-2
3a,4,7,7a-Tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione; N-(trichloromethylthio)-4-cyclohexene-1,2-dicarboximide; N-trichloromethylthio-3a,4,7,7a-tetrahydrophthalimide; N-trichloromethylmercapto-4-cyclohexene-1,2-dicarboximide; N-(trichloromethylmercapto)-Δ4-tetrahydrophthalimide; ENT-26538; SR-406; Merpan; Orthocide-406; Vancide 89.
C9H8Cl3NO2S; mol wt 300.59.
C 35.96%, H 2.68%, Cl 35.38%, N 4.66%, O 10.65%, S 10.67%.

Description and references

Prepn: A. R. Kittleson, US 2553771; US 2653155; US 2713058 (1951, 1953, 1955 all to Standard Oil); idem, Science 115, 84 (1952); idem, J. Agric. Food Chem. 1, 677 (1953). Colorimetric determination: A. R. Kittleson, Anal. Chem. 24, 1173 (1952). Review of mutagenicity studies: B. A. Bridges, Mutat. Res. 32, 3 (1975); of carcinogenic risk: IARC Monographs 30, 295-318 (1983).

Chemical structure

Properties

Odorless crystals from CCl4, mp 178°. d 1.74. Practically insol in water. Soly at 26° in g/100 ml: chloroform 7.78; tetrachloroethane 8.15; cyclohexanone 4.96; dioxane 4.70; benzene 2.13; toluene 0.69; heptane 0.04; ethanol 0.29; ether 0.25. LD50 orally in rats: 9000 mg/kg (Bridges).

Caution

Potential symptoms of overexposure are irritation of eyes, skin, upper respiratory system; blurred vision; dermatitis, skin sensitization; dyspnea; diarrhea, vomiting. Potential occupational carcinogen. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 50.

Use

Fungicide; bacteriostat in soap.