Pyraclofos

Basic Info

Common NamePyraclofos(F05753)
2D Structure
FRCD IDF05753
CAS Number89784-60-1
PubChem CID93460
FormulaC14H18ClN2O3PS
IUPAC Name

1-(4-chlorophenyl)-4-[ethoxy(propylsulfanyl)phosphoryl]oxypyrazole

InChI Key

QHGVXILFMXYDRS-UHFFFAOYSA-N

InChI

InChI=1S/C14H18ClN2O3PS/c1-3-9-22-21(18,19-4-2)20-14-10-16-17(11-14)13-7-5-12(15)6-8-13/h5-8,10-11H,3-4,9H2,1-2H3

Canonical SMILES

CCCSP(=O)(OCC)OC1=CN(N=C1)C2=CC=C(C=C2)Cl

Isomeric SMILES

CCCSP(=O)(OCC)OC1=CN(N=C1)C2=CC=C(C=C2)Cl

Synonyms
        
            Voltage
        
            O-[1-(4-chlorophenyl)-1H-pyrazol-4-yl] O-ethyl S-propyl phosphorothioate
        
            Pyraclofos
        
            Boltage
        
            starlet
        
            Pyraclofos [ISO]
        
            77458-01-6
        
            89784-60-1
        
            TIA 230
        
            Phosphorothioic acid, O-(1-(4-chlorophenyl)-1H-pyrazol-4-yl) O-ethyl S-propyl ester
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassAzoles
SubclassPyrazoles
Intermediate Tree NodesNot available
Direct ParentPhenylpyrazoles
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPhenylpyrazole - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Heteroaromatic compound - Sulfenyl compound - Organothiophosphorus compound - Azacycle - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.

Properties

Property NameProperty Value
Molecular Weight360.793
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Complexity383
Monoisotopic Mass360.046
Exact Mass360.046
XLogP3.8
Formal Charge0
Heavy Atom Count22
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+0.9426
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2-0.5480
P-glycoprotein SubstrateNon-substrate0.8368
P-glycoprotein InhibitorNon-inhibitor0.6206
Non-inhibitor0.7767
Renal Organic Cation TransporterNon-inhibitor0.8405
Distribution
Subcellular localizationMitochondria0.5602
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7091
CYP450 2D6 SubstrateNon-substrate0.7695
CYP450 3A4 SubstrateSubstrate0.5746
CYP450 1A2 InhibitorInhibitor0.6154
CYP450 2C9 InhibitorInhibitor0.5688
CYP450 2D6 InhibitorNon-inhibitor0.8629
CYP450 2C19 InhibitorInhibitor0.6430
CYP450 3A4 InhibitorInhibitor0.6449
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.7268
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.6236
Non-inhibitor0.6564
AMES ToxicityNon AMES toxic0.5426
CarcinogensNon-carcinogens0.6914
Fish ToxicityHigh FHMT0.9995
Tetrahymena Pyriformis ToxicityHigh TPT0.9909
Honey Bee ToxicityLow HBT0.5000
BiodegradationNot ready biodegradable0.9797
Acute Oral ToxicityII0.7176
Carcinogenicity (Three-class)Non-required0.4973
Model Value Unit
Absorption
Aqueous solubility-4.6048LogS
Caco-2 Permeability1.0713LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.1518LD50, mol/kg
Fish Toxicity1.0248pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8200pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Umbelliferous VegetablesJapan0.05ppm
Other Terrestrial Mammals,Edible OffalJapan0.1ppm
Other Terrestrial Mammals,KidneyJapan0.1ppm
Other Terrestrial Mammals,LiverJapan0.1ppm
Other Terrestrial Mammals,FatJapan0.1ppm
Other Terrestrial Mammals,MuscleJapan0.1ppm
Other HerbsJapan0.5ppm
Other SpicesJapan1ppm
Other VegetablesJapan0.05ppm
OkraJapan0.05ppm
SpinachJapan0.05ppm
Other Solanceous VegetablesJapan0.05ppm
Pimiento(Sweet Pepper)Japan0.05ppm
MitsubaJapan0.05ppm
CeleryJapan0.05ppm
ParsleyJapan0.05ppm
Multiplying OnionJapan0.05ppm
AsparagusJapan0.05ppm
Welsh(Including Leek)Japan0.05ppm
Other Composite VegetablesJapan0.05ppm

References

TitleJournalDatePubmed ID
Different enantioselective degradation of pyraclofos in soils.J Agric Food Chem2012 May 222494269
Enantiomeric separation and toxicity of an organophosporus insecticide, pyraclofos.J Agric Food Chem2012 Jul 1822708718
Risk assessment of the organophosphate pesticides isazofos and pyraclofos using a21-day dietary toxicity study in Japanese quail.Ecotoxicol Environ Saf2008 Sep17629558
[A rapid multi-residual analysis for organophosphorus pesticides in the products of animal origin using gas chromatography coupled with accelerated solventextraction and gel permeation chromatographic purification].Se Pu2008 Sep19160756
Nonaqueous and aqueous-organic media for the enantiomeric separations of neutral organophosphorus pesticides by CE.Electrophoresis2007 Aug17592615
[Multiresidue analysis of organophosphorus pesticides in vegetables and fruitsusing dual-column GC-FPD, -NPD].Shokuhin Eiseigaku Zasshi2001 Dec11875824