Thiophanate

Basic Info

Common NameThiophanate(F06024)
2D Structure
FRCD IDF06024
CAS Number
PubChem CID3032792
FormulaC14H18N4O4S2
IUPAC Name

ethyl N-[[2-(ethoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate

InChI Key

YFNCATAIYKQPOO-UHFFFAOYSA-N

InChI

InChI=1S/C14H18N4O4S2/c1-3-21-13(19)17-11(23)15-9-7-5-6-8-10(9)16-12(24)18-14(20)22-4-2/h5-8H,3-4H2,1-2H3,(H2,15,17,19,23)(H2,16,18,20,24)

Canonical SMILES

CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC

Isomeric SMILES

CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC

Synonyms
        
            THIOPHANATE ETHYL
        
            Thiophanate
        
            Ethyl thiophanate
        
            Thiophanat
        
            Thiofanate
        
            Cercobin
        
            Enovit
        
            Topsin
        
            Thiophanate-Ethyl
        
            Nemafax
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsMonocyclic benzene moiety - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Imine - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Properties

Property NameProperty Value
Molecular Weight370.442
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Complexity434
Monoisotopic Mass370.077
Exact Mass370.077
XLogP3.3
Formal Charge0
Heavy Atom Count24
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.5761
Human Intestinal AbsorptionHIA-0.5659
Caco-2 PermeabilityCaco2-0.6073
P-glycoprotein SubstrateNon-substrate0.6511
P-glycoprotein InhibitorNon-inhibitor0.7856
Non-inhibitor0.9904
Renal Organic Cation TransporterNon-inhibitor0.9585
Distribution
Subcellular localizationMitochondria0.8033
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7696
CYP450 2D6 SubstrateNon-substrate0.8158
CYP450 3A4 SubstrateNon-substrate0.7372
CYP450 1A2 InhibitorInhibitor0.8158
CYP450 2C9 InhibitorNon-inhibitor0.5324
CYP450 2D6 InhibitorNon-inhibitor0.8990
CYP450 2C19 InhibitorInhibitor0.5490
CYP450 3A4 InhibitorNon-inhibitor0.8486
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7905
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9789
Non-inhibitor0.9051
AMES ToxicityAMES toxic0.6073
CarcinogensNon-carcinogens0.7772
Fish ToxicityHigh FHMT0.9990
Tetrahymena Pyriformis ToxicityHigh TPT0.9908
Honey Bee ToxicityLow HBT0.6696
BiodegradationNot ready biodegradable0.9715
Acute Oral ToxicityIII0.4968
Carcinogenicity (Three-class)Non-required0.6284
Model Value Unit
Absorption
Aqueous solubility-3.6693LogS
Caco-2 Permeability0.6800LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1134LD50, mol/kg
Fish Toxicity1.6063pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4018pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Broad BeansAustralia0.5mg/kg
AvocadoAustralia3mg/kg
SimazineAustralia0.1mg/kg
Citrus FruitsAustralia10mg/kg
PeanutsAustralia0. 2mg/kg
LitchisAustralia10mg/kg
MangoesAustralia5mg/kg
MushroomsAustralia10mg/kg
GrapeAustralia3mg/kg
VegetableAustralia3mg/kg
BananasAustralia1mg/kg
LentilsAustralia0.5mg/kg

References

TitleJournalDatePubmed ID
Determination of residual levels of naloxone, yohimbine, thiophanate, andaltrenogest in porcine muscle using QuEChERS with liquid chromatography andtriple quadrupole mass spectrometry.J Sep Sci2016 Mar26697949
Comparison of extraction solvents and sorbents in the quick, easy, cheap,effective, rugged, and safe method for the determination of pesticidemultiresidue in fruits by ultra high performance liquid chromatography withtandem mass spectrometry.J Sep Sci2015 Oct26312397
Effect of preharvest anti-fungal compounds on Aspergillus steynii and A. carbonarius under fluctuating and extreme environmental conditions.Int J Food Microbiol2012 Oct 122947301
Determination of carbendazim, thiophanate, thiophanate-methyl and benomylresidues in agricultural products by liquid chromatography-tandem massspectrometry.Shokuhin Eiseigaku Zasshi201121720119
Oral pharmacological treatments for parasitic diseases of rainbow troutoncorhynchus mykiss. III. Ichthyobodo necator.Dis Aquat Organ1998 Jul 309745716
Oral pharmacological treatments for parasitic diseases of rainbow troutOncorhynchus mykiss. II. Gyrodactylus sp.Dis Aquat Organ1998 Jul 309745715
[Ethyl benzimidazole carbamate: teratogenic effect and presence in the milk ofcows after administration of thiophanate].Ann Rech Vet19902344141