Phenthoate

Basic Info

Common NamePhenthoate(F05889)
2D Structure
FRCD IDF05889
CAS Number2597-03-7
PubChem CID17435
FormulaC12H17O4PS2
IUPAC Name

ethyl 2-dimethoxyphosphinothioylsulfanyl-2-phenylacetate

InChI Key

XAMUDJHXFNRLCY-UHFFFAOYSA-N

InChI

InChI=1S/C12H17O4PS2/c1-4-16-12(13)11(10-8-6-5-7-9-10)19-17(18,14-2)15-3/h5-9,11H,4H2,1-3H3

Canonical SMILES

CCOC(=O)C(C1=CC=CC=C1)SP(=S)(OC)OC

Isomeric SMILES

CCOC(=O)C(C1=CC=CC=C1)SP(=S)(OC)OC

Synonyms
        
            Dimefenthoat
        
            PHENTHOATE
        
            Fenthoate
        
            Dimephenthioate
        
            Dimephenthoate
        
            Cidial
        
            Phendal
        
            Elsan
        
            2597-03-7
        
            Cidemul
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 - Dithiophosphate o-ester - Dithiophosphate s-ester - Organic dithiophosphate - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organothiophosphorus compound - Sulfenyl compound - Organooxygen compound - Organic oxygen compound - Organic oxide - Organosulfur compound - Carbonyl group - Hydrocarbon derivative - 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 Weight320.358
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Complexity324
Monoisotopic Mass320.031
Exact Mass320.031
XLogP3.7
Formal Charge0
Heavy Atom Count19
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9326
Human Intestinal AbsorptionHIA+0.9895
Caco-2 PermeabilityCaco2+0.5328
P-glycoprotein SubstrateNon-substrate0.7964
P-glycoprotein InhibitorNon-inhibitor0.7814
Non-inhibitor0.9737
Renal Organic Cation TransporterNon-inhibitor0.9252
Distribution
Subcellular localizationMitochondria0.7739
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7629
CYP450 2D6 SubstrateNon-substrate0.8523
CYP450 3A4 SubstrateNon-substrate0.6087
CYP450 1A2 InhibitorNon-inhibitor0.6641
CYP450 2C9 InhibitorNon-inhibitor0.6506
CYP450 2D6 InhibitorNon-inhibitor0.9335
CYP450 2C19 InhibitorNon-inhibitor0.6772
CYP450 3A4 InhibitorNon-inhibitor0.6014
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6446
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9672
Non-inhibitor0.9457
AMES ToxicityNon AMES toxic0.9133
CarcinogensCarcinogens 0.5280
Fish ToxicityHigh FHMT0.9390
Tetrahymena Pyriformis ToxicityHigh TPT0.9852
Honey Bee ToxicityHigh HBT0.9398
BiodegradationNot ready biodegradable0.7808
Acute Oral ToxicityII0.7458
Carcinogenicity (Three-class)Non-required0.7393
Model Value Unit
Absorption
Aqueous solubility-4.2610LogS
Caco-2 Permeability0.9726LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.6144LD50, mol/kg
Fish Toxicity1.5869pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5164pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
EndiveJapan0.1ppm
ChicoryJapan0.1ppm
ArtichokeJapan0.1ppm
SalsifyJapan0.1ppm
BurdockJapan0.1ppm
Seed spices0810000European Union701/09/2008
Anise/aniseed0810010European Union701/09/2008
Black caraway/black cumin (Nigella,)0810020European Union701/09/2008
Celery (Angelica, Lovage,)0810030European Union701/09/2008
Coriander (Culantro/false coriander,)0810040European Union701/09/2008
Cumin0810050European Union701/09/2008
Dill0810060European Union701/09/2008
Fennel (Bitter fennel, Sweet fennel,)0810070European Union701/09/2008
Fenugreek0810080European Union701/09/2008
Nutmeg (Annatto, Candlenut, Wattleseeds, Calabash nutmeg,)0810090European Union701/09/2008
Others (2)0810990European Union701/09/2008
Orange(Including Navel Orange)Japan0.1ppm
Japanese Radish,Leaves(Including Radish)Japan0.1ppm
Other Spices,Dried(Limited To Seeds)Japan７ppm
Other HerbsJapan0.1ppm

References

TitleJournalDatePubmed ID
Determination of carbamate and organophosphorus pesticides in vegetable samplesand the efficiency of gamma-radiation in their removal.Biomed Res Int201424711991
Solid-phase microextraction-liquid chromatography-mass spectrometry applied tothe analysis of insecticides in honey.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2008Jan17852391
Synthesis of three haptens for the class-specific immunoassay of O,O-dimethylorganophosphorus pesticides and effect of hapten heterology on immunoassaysensitivity.Anal Chim Acta2008 May 1918442523
Toxicity of insecticides to the sweetpotato whitefly (Hemiptera: Aleyrodidae) andits natural enemies.Pest Manag Sci2007 Jul17523144
[Detection of O,O,S-trimethyl phosphorodithioate, an impurity in phenthoate(PAP), in komatsuna].Shokuhin Eiseigaku Zasshi2001 Jun11577395
Degradation of malathion and phenthoate by glutathione reductase in wheat germ.J Agric Food Chem2000 Jun10888576
Determination of organophosphorus pesticides in wheat flour by supercriticalfluid extraction and gas chromatography with nitrogen-phosphorus detection.J Chromatogr A1998 Oct 169818429
Selective, solid-matrix dispersion extraction of organophosphate pesticideresidues from milk.J Chromatogr A1996 Nov 228997741