Captan (CHEM002765)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (19)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:50 UTC
Update Date2016-11-09 01:08:58 UTC
Accession NumberCHEM002765
Identification
Common NameCaptan
ClassSmall Molecule
DescriptionCaptan is the name of a general use pesticide (GUP) that belongs to the phthalimide class of fungicides. Though it can be applied on its own, Captan is often added as a component of other pesticide mixtures. It is used to control diseases on a number of fruits and vegetables as well as ornamental plants. It also improves the outward appearance of many fruits, making them brighter and healthier-looking. Captan is thought to be a potential carcinogen at prolonged high doses that cause cytotoxicity and regenerative cell hyperplasia. These high doses of captan are many orders of magnitude above those likely to be consumed in the diet, or encountered by individuals in occupational or residential settings. Therefore, captan is not likely to be a human carcinogen nor pose cancer risks of concern.
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Fungicide
  • Household Toxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,2,3,6-Tetrahydro-N-(trichloromethylthio)phthalimideChEBI
3a,4,7,7a-Tetrahydro-2-((trichloromethyl)thio)-1H-isoindole-1,3(2H)-dioneChEBI
3a,4,7,7a-Tetrahydro-N-(trichloromethanesulphenyl)phthalimideChEBI
AmercideChEBI
BangtonChEBI
CaptabChEBI
CaptadinChEBI
CaptafChEBI
CaptaneChEBI
CaptanexChEBI
CaptexChEBI
ent 26,538ChEBI
HexacapChEBI
KaptanChEBI
MalipurChEBI
MerpanChEBI
N-(Trichloromethylmercapto)-Delta(4)-tetrahydrophthalimideChEBI
N-[(Trichloromethyl)thio]tetrahydrophthalimideChEBI
N-Trichloromethylmercapto-4-cyclohexene-1,2-dicarboximideChEBI
N-Trichloromethylthio-3a,4,7,7a-tetrahydrophthalimideChEBI
N-Trichloromethylthiocyclohex-4-ene-1,2-dicarboximideChEBI
NeracidChEBI
OrthocideChEBI
OsocideChEBI
SR 406ChEBI
SR406ChEBI
VanicideChEBI
VenturinChEBI
VondcaptanChEBI
ZenecalChEBI
3a,4,7,7a-Tetrahydro-N-(trichloromethanesulfenyl)phthalimideGenerator
N-(Trichloromethylmercapto)-δ(4)-tetrahydrophthalimideGenerator
N Trichloromethylthio 4 cyclohexane 1,2 dicarboximideMeSH
Vancide 89MeSH
N-Trichloromethylthio-4-cyclohexane-1,2-dicarboximideMeSH
Chemical FormulaC9H8Cl3NO2S
Average Molecular Mass300.589 g/mol
Monoisotopic Mass298.934 g/mol
CAS Registry Number133-06-2
IUPAC Name2-[(trichloromethyl)sulfanyl]-2,3,3a,4,7,7a-hexahydro-1H-isoindole-1,3-dione
Traditional Namecaptan
SMILESClC(Cl)(Cl)SN1C(=O)C2CC=CCC2C1=O
InChI IdentifierInChI=1S/C9H8Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-2,5-6H,3-4H2
InChI KeyLDVVMCZRFWMZSG-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
  • 2-pyrrolidone
  • Pyrrolidone
  • Dicarboximide
  • Pyrrolidine
  • Trihalomethane
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Sulfenyl compound
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Halomethane
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • 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 Point178°C (decomposes)
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
logP3ALOGPS
logP3.25ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)17.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area37.38 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.22 m³·mol⁻¹ChemAxon
Polarizability26.22 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, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-49c11a746be2aee8cc86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-1980000000-59b02ac1d4ac2f50a36bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2910000000-32132bddb69e38ba1cf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-dbda73f8735fd06e528eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0490000000-91af5f5b11d599c14627Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00nb-4940000000-030c1d9ea17c21356ca3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-01e24abd8eebd54c0bf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0950000000-997a5433d91530b95a2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9540000000-7cfa7ef3c2c74ab9a0f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-5eee0efe16ae55dd7855Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-d88ba96c55151bc3362dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-7910000000-d23011af51ae93113acbSpectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9400000000-a89083cd57a8373e0683Spectrum
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)3, not classifiable as to its carcinogenicity 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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCaptan
Chemspider IDNot Available
ChEBI ID34608
PubChem Compound ID8606
Kegg Compound IDC14438
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20433167
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20569196
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21121628
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21381057
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21381058
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23692481
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23742211
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=6578186
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=9530801