Captafol

Title: Captafol
CAS Registry Number: 2425-06-1
CAS Name: 3a,4,7,7a-Tetrahydro-2-[(1,1,2,2-tetrachloroethyl)thio]-1H-isoindole-1,3(2H)-dione
Additional Names: N-(1,1,2,2-tetrachloroethylthio)-4-cyclohexene-1,2-dicarboximide; N-(1,1,2,2-tetrachloroethylmercapto)-4-cyclohexene-1,2-dicarboximide; N-(1,1,2,2-tetrachloroethylthio)-D4-tetrahydrophthalimide; N-(1,1,2,2-tetrachloroethylsulfenyl)-cis-4-cyclohexene-1,2-dicarboximide; Difolatan
Molecular Formula: C10H9Cl4NO2S
Molecular Weight: 349.06
Percent Composition: C 34.41%, H 2.60%, Cl 40.63%, N 4.01%, O 9.17%, S 9.19%
Literature References: N-tetrachloroethyl analog of captan, q.v. Prepn: Kohn, BE 633205 (1963 to California Res. Corp.), C.A. 60, 15789cd (1964). Toxicology: R. Ben-Dyke et al., World Rev. Pest Control 9, 119 (1970); G. L. Kennedy, Jr. et al., Food Cosmet. Toxicol. 13, 55 (1975). Carcinogenicity study: S. Tamano et al., Jpn. J. Cancer Res. 81, 1222 (1990).
Properties: Crystals, mp 160-161°. LD50 in rats, rabbits (mg/kg): 2500-6200 orally; 15400 dermally (Ben-Dyke).
Melting point: mp 160-161°
Toxicity data: LD50 in rats, rabbits (mg/kg): 2500-6200 orally; 15400 dermally (Ben-Dyke)
CAUTION: Potential symptoms of overexposure are irritation of eyes, skin, respiratory system; dermatitis, skin sensitization; conjunctivitis; bronchitis, wheezing; diarrhea, vomiting; liver and kidney injury; high blood pressure. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 50.
Use: Agricultural fungicide, especially for potatoes.
Captodiamine Capuride Caraway Carazolol Carbachol

Captafol
Captafol.png
Identifiers
CAS number 2425-06-1 YesY
PubChem 17038
ChemSpider 17215880 YesY
UNII D88BWD4H64 YesY
KEGG C18754 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H9Cl4NO2S
Molar mass 349.06 g mol−1
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Captafol is a fungicide.[1] It is used to control almost all fungal diseases of plants except powdery mildews.[2] It is believed to be a human carcinogen, and production for use as a fungicide in the United States stopped in 1987. Its continued use from existing stocks was allowed, but in 1999 the Environmental Protection Agency banned its use on all crops except onions, potatoes, and tomatoes. In 2006 even these exceptions were disallowed, so currently its use on all crops is banned in the United States. Several other countries have followed suit since 2000, and as of 2010, no countries are known to allow the use of captafol on food crops.[3] Currently, the National Institute for Occupational Safety and Health established a recommended exposure limit of 0.1 mg/m3 for dermal exposures.[4]

Captafol was disclosed in US patent 3,178,447 (1965).[5] Its synergistic mixture with thiabendazol was described in US patent 4092422 (1978).[6]

International trade in captafol is regulated by the Rotterdam Convention.