# Captafol

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Captafol Names Preferred IUPAC name (3aR,7aS)-2-[(1,1,2,2-Tetrachloroethyl)sulfanyl]-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione Other names cis-Captafol; Merpafol; Crisfolatan; Sulfonimide; Sulpheimide; Arborseal; Captaspor; Mycodifol; Pillartan; Terrazol; Difolatan Identifiers CAS Number 2425-06-1 Y 3D model (JSmol) Interactive image ChEBI CHEBI:81938 N ChemSpider 17215880 Y ECHA InfoCard 100.017.604 KEGG C18754 Y PubChem CID 17038 UNII D88BWD4H64 Y CompTox Dashboard (EPA) DTXSID4020242 InChI InChI=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+ Y Key: JHRWWRDRBPCWTF-OLQVQODUSA-N Y 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+ Key: JHRWWRDRBPCWTF-OLQVQODUBH SMILES ClC(Cl)C(Cl)(Cl)SN1C(=O)[C@H]2C\C=C/C[C@H]2C1=O Properties Chemical formula C10H9Cl4NO2S Molar mass 349.05 g·mol−1 Appearance White, crystalline solid Melting point 161 °C; 321 °F; 434 K[1] Boiling point decomposes Solubility in water 0.0001%[1] Vapor pressure 0.000008 mmHg (20°C) [1] Hazards Occupational safety and health (OHS/OSH): Main hazards potential occupational carcinogen Flash point noncombustible[1] NIOSH (US health exposure limits): PEL (Permissible) none[1] REL (Recommended) Ca TWA 0.1 mg/m3 [skin][1] IDLH (Immediate danger) N.D.[1] Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

**Captafol** is a [fungicide](/source/Fungicide).[2] It is used to control almost all fungal diseases of plants except powdery mildews.[2] It is believed to be a human [carcinogen](/source/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](/source/United_States_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](/source/National_Institute_for_Occupational_Safety_and_Health) established a [recommended exposure limit](/source/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 [thiabendazole](/source/Thiabendazole) was described in US patent 4092422 (1978).[6]

International trade in captafol is regulated by the [Rotterdam Convention](/source/Rotterdam_Convention).

## Synthesis

Captafol can be obtained by reacting the sodium salt of [1,2,3,6-Tetrahydrophthalimide](https://en.wikipedia.org/w/index.php?title=1,2,3,6-Tetrahydrophthalimide&action=edit&redlink=1) in benzene with [1,1,2,2-Tetrachloroethylsulfenyl chloride](https://en.wikipedia.org/w/index.php?title=1,1,2,2-Tetrachloroethylsulfenyl_chloride&action=edit&redlink=1).[7][8]

Synthesis of Captafol

## References

1. ^ [***a***](#cite_ref-PGCH_1-0) [***b***](#cite_ref-PGCH_1-1) [***c***](#cite_ref-PGCH_1-2) [***d***](#cite_ref-PGCH_1-3) [***e***](#cite_ref-PGCH_1-4) [***f***](#cite_ref-PGCH_1-5) [***g***](#cite_ref-PGCH_1-6) NIOSH Pocket Guide to Chemical Hazards. ["#0098"](https://www.cdc.gov/niosh/npg/npgd0098.html). [National Institute for Occupational Safety and Health](/source/National_Institute_for_Occupational_Safety_and_Health) (NIOSH).

1. ^ [***a***](#cite_ref-extoxnet_2-0) [***b***](#cite_ref-extoxnet_2-1) [Captafol](http://extoxnet.orst.edu/pips/captafol.htm) from Extension Toxicology Network

1. **[^](#cite_ref-3)** [Captafol CAS No. 2425-06-1 Reasonably anticipated to be a human carcinogen](https://ntp.niehs.nih.gov/sites/default/files/ntp/roc/content/profiles/captafol.pdf) *[National Institute of Health](/source/National_Institute_of_Health)*, Report on Carcinogens, Twelfth Edition (2011)

1. **[^](#cite_ref-4)** [NIOSH Pocket Guide to Chemical Hazards](https://www.cdc.gov/niosh/npg/npgd0098.html) from Centers of Disease Control and Prevention

1. **[^](#cite_ref-5)** ["N-polyhaloalkylthio compounds"](http://ip.com/patent/US3178447). 1965-04-13. US patent 3,178,447.. The term "captafol" is not used in this publication, but is described as disclosed in this patent in [patent application 20080269051](http://www.faqs.org/patents/app/20080269051)

1. **[^](#cite_ref-6)** ["Synergistic fungicidal mixture of captafol and thiabendazol \[*sic*\]"](https://web.archive.org/web/20111001222129/http://www.patentlens.net/patentlens/patents.html?patnums=US_4092422). US patent via PatentLens. Archived from [the original](http://www.patentlens.net/patentlens/patents.html?patnums=US_4092422) on 2011-10-01. Retrieved 2011-06-17.

1. **[^](#cite_ref-HSDB_7-0)** [NLM](/source/National_Library_of_Medicine) [Hazardous Substances Data Bank](/source/Hazardous_Substances_Data_Bank) entry for [ ]

1. **[^](#cite_ref-8)** Thomas A. Unger: Pesticide Synthesis Handbook. William Andrew, 1996, ISBN 0-8155-1853-6, p. 453

## Further reading

- *[Captafol](http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/113.htm)* in the Pesticide Properties DataBase (PPDB)

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Adapted from the Wikipedia article [Captafol](https://en.wikipedia.org/wiki/Captafol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Captafol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.