Basic Info

Common NamePirimiphos-Ethyl(F05926)
2D Structure
FRCD IDF05926
CAS Number23505-41-1
PubChem CID31957
FormulaC13H24N3O3PS
IUPAC Name

4-diethoxyphosphinothioyloxy-N,N-diethyl-6-methylpyrimidin-2-amine

InChI Key

TZBPRYIIJAJUOY-UHFFFAOYSA-N

InChI

InChI=1S/C13H24N3O3PS/c1-6-16(7-2)13-14-11(5)10-12(15-13)19-20(21,17-8-3)18-9-4/h10H,6-9H2,1-5H3

Canonical SMILES

CCN(CC)C1=NC(=CC(=N1)OP(=S)(OCC)OCC)C

Isomeric SMILES

CCN(CC)C1=NC(=CC(=N1)OP(=S)(OCC)OCC)C

Synonyms
        
            Pirimiphos ethyl
        
            Ethyl pirimiphos
        
            Pirimiphos-ethyl
        
            Pirimifosethyl
        
            Primicid
        
            Primotec
        
            Fernex
        
            Solgard
        
            23505-41-1
        
            PIRIMIFOS-ETHYL
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
SubclassThiophosphoric acid esters
Intermediate Tree NodesAryl thiophosphates
Direct ParentPyrimidinyl phosphorothioates
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPyrimidinyl phosphorothioate - Dialkylarylamine - Thiophosphate triester - Aminopyrimidine - Pyrimidine - Heteroaromatic compound - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom.

Properties

Property NameProperty Value
Molecular Weight333.387
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count9
Complexity335
Monoisotopic Mass333.128
Exact Mass333.128
XLogP4.8
Formal Charge0
Heavy Atom Count21
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+0.9759
Human Intestinal AbsorptionHIA+0.9804
Caco-2 PermeabilityCaco2-0.5417
P-glycoprotein SubstrateNon-substrate0.7055
P-glycoprotein InhibitorNon-inhibitor0.5752
Non-inhibitor0.9906
Renal Organic Cation TransporterNon-inhibitor0.8505
Distribution
Subcellular localizationMitochondria0.4732
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7792
CYP450 2D6 SubstrateNon-substrate0.7382
CYP450 3A4 SubstrateNon-substrate0.5000
CYP450 1A2 InhibitorNon-inhibitor0.5541
CYP450 2C9 InhibitorNon-inhibitor0.6112
CYP450 2D6 InhibitorNon-inhibitor0.8912
CYP450 2C19 InhibitorNon-inhibitor0.5527
CYP450 3A4 InhibitorNon-inhibitor0.5418
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8089
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8733
Non-inhibitor0.7680
AMES ToxicityNon AMES toxic0.6895
CarcinogensNon-carcinogens0.7193
Fish ToxicityLow FHMT0.5596
Tetrahymena Pyriformis ToxicityHigh TPT0.7471
Honey Bee ToxicityHigh HBT0.7855
BiodegradationNot ready biodegradable0.9835
Acute Oral ToxicityII0.7258
Carcinogenicity (Three-class)Non-required0.6036

Model Value Unit
Absorption
Aqueous solubility-3.9170LogS
Caco-2 Permeability1.1026LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.3457LD50, mol/kg
Fish Toxicity1.7430pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3476pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
GarlicKorea00.1ppm
PeanutsKorea0.1ppm
BananasKorea0.02ppm

References

TitleJournalDatePubmed ID
Multiresidue method for simultaneous analysis of aflatoxin M1, avermectins, organophosphate pesticides and milbemycin in milk by ultra-performance liquid chromatography coupled to tandem mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2016 Jun27144891