Captafol

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title: "Captafol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["fungicides", "imides", "organochlorides", "sulfenamides", "lactams", "iarc-group-2a-carcinogens"] topic_path: "general/fungicides" source: "https://en.wikipedia.org/wiki/Captafol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 445168738 | ImageFile=Captafol.png | PIN=(3aR,7aS)-2-[(1,1,2,2-Tetrachloroethyl)sulfanyl]-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione | OtherNames=cis-Captafol; Merpafol; Crisfolatan; Sulfonimide; Sulpheimide; Arborseal; Captaspor; Mycodifol; Pillartan; Terrazol; Difolatan |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 17215880 | UNII_Ref = | UNII = D88BWD4H64 | InChI = 1/C10H9Cl4NO2S/c11-9(12)10(13,14)18-15-7(16)5-3-1-2-4-6(5)8(15)17/h1-2,5-6,9H,3-4H2/t5-,6+ | InChIKey = JHRWWRDRBPCWTF-OLQVQODUBH | StdInChI_Ref = | StdInChI = 1S/C10H9Cl4NO2S/c11-9(12)10(13,14)18-15-7(16)5-3-1-2-4-6(5)8(15)17/h1-2,5-6,9H,3-4H2/t5-,6+ | StdInChIKey_Ref = | StdInChIKey = JHRWWRDRBPCWTF-OLQVQODUSA-N | CASNo_Ref = | CASNo=2425-06-1 | PubChem=17038 | KEGG_Ref = | KEGG = C18754 | ChEBI_Ref = | ChEBI = 81938 | SMILES = ClC(Cl)C(Cl)(Cl)SN1C(=O)[C@H]2C\C=C/C[C@H]2C1=O |Section2={{Chembox Properties | C=10 | H=9 | Cl=4 | N=1 | O=2 | S=1 | Appearance= White, crystalline solid | Density= | MeltingPtF= 321 | MeltingPt_ref = | BoilingPt= decomposes | Solubility= 0.0001% | VaporPressure = 0.000008 mmHg (20°C) |Section3={{Chembox Hazards | MainHazards= potential occupational carcinogen | FlashPt= noncombustible | FlashPt_ref = | AutoignitionPt = | PEL = none | REL = Ca TWA 0.1 mg/m3 [skin] | IDLH = N.D.

Captafol is a fungicide. It is used to control almost all fungal diseases of plants except powdery mildews. Currently, the National Institute for Occupational Safety and Health established a recommended exposure limit of 0.1 mg/m3 for dermal exposures.

Captafol was disclosed in US patent 3,178,447 (1965). Its synergistic mixture with thiabendazole was described in US patent 4092422 (1978).

International trade in captafol is regulated by the Rotterdam Convention.

Synthesis

Captafol can be obtained by reacting the sodium salt of 1,2,3,6-Tetrahydrophthalimide in benzene with 1,1,2,2-Tetrachloroethylsulfenyl chloride.Thomas A. Unger: Pesticide Synthesis Handbook. William Andrew, 1996, ISBN 0-8155-1853-6, p. 453

left|thumb|Synthesis of Captafol

References

References

  1. {{PGCH. 0098
  2. [http://extoxnet.orst.edu/pips/captafol.htm Captafol] from Extension Toxicology Network
  3. 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 [[United States Environmental Protection Agency. 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.[https://ntp.niehs.nih.gov/sites/default/files/ntp/roc/content/profiles/captafol.pdf Captafol CAS No. 2425-06-1 Reasonably anticipated to be a human carcinogen] ''[[National Institute of Health]]'', Report on Carcinogens, Twelfth Edition (2011)
  4. [https://www.cdc.gov/niosh/npg/npgd0098.html NIOSH Pocket Guide to Chemical Hazards] from Centers of Disease Control and Prevention
  5. (1965-04-13). "N-polyhaloalkylthio compounds".
  6. "Synergistic fungicidal mixture of captafol and {{sic". US patent via PatentLens.
  7. {{HSDB

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fungicidesimidesorganochloridessulfenamideslactamsiarc-group-2a-carcinogens