:Captafol

{{chembox

| 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 = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 17215880

| UNII_Ref = {{fdacite|correct|FDA}}

| 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 = {{stdinchicite|correct|chemspider}}

| 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 = {{stdinchicite|correct|chemspider}}

| StdInChIKey = JHRWWRDRBPCWTF-OLQVQODUSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=2425-06-1

| PubChem=17038

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C18754

| ChEBI_Ref = {{ebicite|changed|EBI}}

| 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{{PGCH|0098}}

| REL = Ca TWA 0.1 mg/m³ [skin]

| IDLH = N.D.

}}

}}

Captafol is a fungicide.[http://extoxnet.orst.edu/pips/captafol.htm Captafol] from Extension Toxicology Network It is used to control almost all fungal diseases of plants except powdery mildews. 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.[https://ntp.niehs.nih.gov/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) Currently, the National Institute for Occupational Safety and Health established a recommended exposure limit of 0.1 mg/m³ for dermal exposures.[https://www.cdc.gov/niosh/npg/npgd0098.html NIOSH Pocket Guide to Chemical Hazards] from Centers of Disease Control and Prevention

Captafol was disclosed in US patent 3,178,447 (1965).{{cite web|url=http://ip.com/patent/US3178447|title=N-polyhaloalkylthio compounds|date=1965-04-13|id=US patent 3,178,447}}. The term "captafol" is not used in this publication, but is described as disclosed in this patent in [http://www.faqs.org/patents/app/20080269051 patent application 20080269051] Its synergistic mixture with thiabendazole was described in US patent 4092422 (1978).{{cite web|url=http://www.patentlens.net/patentlens/patents.html?patnums=US_4092422|title=Synergistic fungicidal mixture of captafol and {{sic|nolink=y|reason=error in source|thiabendazol}}|publisher=US patent via PatentLens|access-date=2011-06-17|archive-date=2011-10-01|archive-url=https://web.archive.org/web/20111001222129/http://www.patentlens.net/patentlens/patents.html?patnums=US_4092422|url-status=dead}}

International trade in captafol is regulated by the Rotterdam Convention.