Captafol (CHEM003442)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (21)XML
Record Information
Version1.0
Creation Date2014-08-29 06:51:38 UTC
Update Date2026-03-26 23:26:52 UTC
Accession NumberCHEM003442
Identification
Common NameCaptafol
ClassSmall Molecule
DescriptionCaptafol belongs to the family of Isoindoles and Derivatives. These are polycyclic compounds containing an isoindole moiety, which is structurally characterized by a cyclohexadiene fused to a pyrrole ring. It is a nonsystemic foliar agricultural fungicide, especially for potatoes.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2A
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Food Toxin
  • Fungicide
  • Metabolite
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(Tetrachloroethylthio)tetrahydrophthalimideChEBI
1,2,3,6-Tetrahydro-N-(1,1,2,2-tetrachloroethylthio)phthalimideChEBI
3a,4,7,7a-Tetrahydro-2-[(1,1,2,2-tetrachloroethyl)thio]-1H-isoindole-1,3(2H)-dioneChEBI
3a,4,7,7a-Tetrahydro-N-(1,1,2,2-tetrachloroethanesulphenyl)phthalimideChEBI
CaptasporChEBI
DifolatanChEBI
DifosanChEBI
FolcidChEBI
HaipenChEBI
KenofolChEBI
MerpafolChEBI
N-(1,1,2,2-Tetrachloroethylthio)-Delta(4)-tetrahydrophthalimideChEBI
N-1,1,2,2-Tetrachloroethylmercapto-4-cyclohexene-1,2-carboximideChEBI
N-[(1,1,2,2-Tetrachloroethyl)sulfenyl]-4-cyclohexene-1,2-dicarboximideChEBI
SansporChEBI
TerrazolChEBI
3a,4,7,7a-Tetrahydro-N-(1,1,2,2-tetrachloroethanesulfenyl)phthalimideGenerator
N-(1,1,2,2-Tetrachloroethylthio)-δ(4)-tetrahydrophthalimideGenerator
N-[(1,1,2,2-Tetrachloroethyl)sulphenyl]-4-cyclohexene-1,2-dicarboximideGenerator
3a,4,7,7a-Tetrahydro-2-[(1,1,2,2-tetrachloroethyl)thio]-1H-isoindole-1,3(2H)-dione, 9ciHMDB
AlflocHMDB
ArborsealHMDB
Difolatan, jmafHMDB
FoltafHMDB
Haipen 50HMDB
N-(1,1,2,2-Tetrachloroethylthio)-4-cyclohexene-1,2-dicarboximide, 8ciHMDB
Nalco 7046HMDB
Proxel efHMDB
SaprirearineHMDB
TetrachloroethylthiotetrahydrophthalimideHMDB
N-(Tetrachloroethylthio)tetrahydrophthalimideHMDB
Captafol, (cis)-isomerHMDB
CaptefolHMDB
CaptofolHMDB
Chemical FormulaC10H9Cl4NO2S
Average Molecular Mass349.061 g/mol
Monoisotopic Mass346.911 g/mol
CAS Registry Number2425-06-1
IUPAC Name2-[(1,1,2,2-tetrachloroethyl)sulfanyl]-2,3,3a,4,7,7a-hexahydro-1H-isoindole-1,3-dione
Traditional Namecrisfolatan
SMILESClC(Cl)C(Cl)(Cl)SN1C(=O)C2CC=CCC2C1=O
InChI IdentifierInChI=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
InChI KeyJHRWWRDRBPCWTF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoindoles and derivatives
Sub ClassIsoindolines
Direct ParentIsoindolones
Alternative Parents
Substituents
  • Isoindolone
  • Isoindole
  • Pyrrolidone
  • 2-pyrrolidone
  • Dicarboximide
  • Pyrrolidine
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Sulfenyl compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alkyl chloride
  • Alkyl halide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point160 - 161°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP3.57ALOGPS
logP3.95ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)17.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area37.38 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity77.49 m³·mol⁻¹ChemAxon
Polarizability30.03 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9700000000-7c112c6aff5bc992788bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0109000000-5273503de88addacd050Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0900000000-731117cd44833cb4f1a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w29-7930000000-d436fd19ac460c146bdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0901000000-33d988dc5870bfed800cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-0914000000-a0ecdec0fd1e79ec9e1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3900000000-ca9ad7ba56ff30cd6b02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-829864d315d3707de67fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-cca0800d42f20fdb2d03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-6900000000-d74d3c0c1f38dcc80969Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-8e640e8707a5054f2e48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1409000000-9ba3ebf26414178ae16aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0g4u-9843000000-52bfa296d6531325a760Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9512000000-ea55ac48cb3b2d20f9daSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (1)
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031669
FooDB IDFDB008329
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCaptafol
Chemspider ID16139
ChEBI ID81938
PubChem Compound ID17038
Kegg Compound IDC18754
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=159800
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1842583
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21822319
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=8426061
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.