Pyrazophos

Basic Info

Common NamePyrazophos(F05729)
2D Structure
FRCD IDF05729
CAS Number13457-18-6
PubChem CID26033
FormulaC14H20N3O5PS
IUPAC Name

ethyl 2-diethoxyphosphinothioyloxy-5-methylpyrazolo[1,5-a]pyrimidine-6-carboxylate

InChI Key

JOOMJVFZQRQWKR-UHFFFAOYSA-N

InChI

InChI=1S/C14H20N3O5PS/c1-5-19-14(18)11-9-17-12(15-10(11)4)8-13(16-17)22-23(24,20-6-2)21-7-3/h8-9H,5-7H2,1-4H3

Canonical SMILES

CCOC(=O)C1=CN2C(=CC(=N2)OP(=S)(OCC)OCC)N=C1C

Isomeric SMILES

CCOC(=O)C1=CN2C(=CC(=N2)OP(=S)(OCC)OCC)N=C1C

Synonyms
        
            Hoechst 2873
        
            PYRAZOPHOS
        
            Curamil
        
            Afugan
        
            Missile
        
            13457-18-6
        
            HOE 2873
        
            Caswell No. 714D
        
            Pyrazophos [BSI:ISO]
        
            UNII-BEG0A8I17D
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 NodesNot available
Direct ParentAryl thiophosphates
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsAryl thiophosphate - Pyrazolo[1,5-a]pyrimidine - Pyrimidine-5-carboxylic acid or derivatives - Pyrimidine-5-carboxylic acid - Pyrazolopyrimidine - Thiophosphate triester - Pyrimidine - Azole - Pyrazole - Heteroaromatic compound - Vinylogous amide - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aryl thiophosphates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where at least one R-group is an aryl group.

Properties

Property NameProperty Value
Molecular Weight373.364
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Complexity473
Monoisotopic Mass373.086
Exact Mass373.086
XLogP3.1
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+0.7970
Human Intestinal AbsorptionHIA+0.9970
Caco-2 PermeabilityCaco2-0.5731
P-glycoprotein SubstrateNon-substrate0.7539
P-glycoprotein InhibitorNon-inhibitor0.6803
Non-inhibitor0.9853
Renal Organic Cation TransporterNon-inhibitor0.9272
Distribution
Subcellular localizationMitochondria0.5392
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7170
CYP450 2D6 SubstrateNon-substrate0.7719
CYP450 3A4 SubstrateSubstrate0.5288
CYP450 1A2 InhibitorNon-inhibitor0.5330
CYP450 2C9 InhibitorNon-inhibitor0.5567
CYP450 2D6 InhibitorNon-inhibitor0.9123
CYP450 2C19 InhibitorNon-inhibitor0.5811
CYP450 3A4 InhibitorInhibitor0.8894
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7980
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9626
Non-inhibitor0.8991
AMES ToxicityNon AMES toxic0.5578
CarcinogensNon-carcinogens0.7652
Fish ToxicityHigh FHMT0.9891
Tetrahymena Pyriformis ToxicityHigh TPT0.8809
Honey Bee ToxicityHigh HBT0.7282
BiodegradationNot ready biodegradable0.8607
Acute Oral ToxicityII0.7317
Carcinogenicity (Three-class)Non-required0.6762
Model Value Unit
Absorption
Aqueous solubility-3.5845LogS
Caco-2 Permeability0.7468LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.2654LD50, mol/kg
Fish Toxicity1.4645pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4478pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
(d) any other parts of the plant (Blond psyllium (seeds, husks), Chamomile (seeds), Cherries (sweet) (stems), China/Jesuit's bark (bark), China/Jesuit's bark (bark), Cocoa (husks), Condurango (bark...0639000European Union0.05*30/12/2015
BeansDenmark0. 2mg/kg
TomatoDenmark0. 2mg/kg
Rape SeedBritain0.05mg/kg
Other Miscellaneous FruitBritain0.05mg/kg
BananasBritain0.05mg/kg
Other Terrestrial Mammals,Edible OffalJapan0.02ppm
Other BerriesJapan0.05ppm
Rice(Brown Rice)Japan0.05ppm
VegetableAustriasee eu mrls
NectarineItaly0.1mg/kg
Loquats/Japanese medlars0130050European Union0.01*30/12/2015
Cherries (sweet) (Black cherries, Capulins, Chokecherries, Cornelian cherries/European corniols, Nanking cherries, Sour cherries/morello cherries,)0140020European Union0.01*30/12/2015
Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E...0154010European Union0.01*30/12/2015
Carambolas (Ambarellas, Aonlas/Indian gooseberries, Babacos, Bilimbis, Cashew apples, Indian jujubes/bers, Jaboticabas, Malay pommarosas/pomeracs, Malayan mombins, Maprangs/marian plums, Natal plum...0161050European Union0.01*30/12/2015
(a) Solanaceae and Malvaceae0231000European Union0.01*30/12/2015
Tomatoes (Alkekengi/Chinese lanterns/ground cherries, Cape gooseberries, Cherry tomatoes, Dwarf Cape gooseberries/strawberry tomatoes, Gojiberries/wolfberries, Gojiberries/wolfberries, Litchi tomat...0231010European Union0.01*30/12/2015
(c) grape leaves and similar species (Climbing wattle/acacia shoots, Malabar nightshades,)0253000European Union0.01*30/12/2015
Celery leaves (Angelica (leaves and stems), Burnet, Caraway leaves, Coriander leaves, Culantro/false coriander leaves, Dill leaves, Fennel leaves, Fenugreek leaves, Herb of grace/rue, Lovage leaves...0256030European Union0.02*30/12/2015
Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L...0256080European Union0.02*30/12/2015

References

TitleJournalDatePubmed ID
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
Validation of a solid-phase microextraction method for the determination oforganophosphorus pesticides in fruits and fruit juice.J Chromatogr A1999 Feb 1210074697
Selective, solid-matrix dispersion extraction of organophosphate pesticideresidues from milk.J Chromatogr A1996 Nov 228997741
Pesticide residues in artichokes: effect of different head shape.J Environ Sci Health B1996 Nov8896357
Analysis of pesticide residues in hops and their extraction by liquid CO2 during the production of hop extracts.Food Addit Contam1994 Sep-Oct7835474
Application of solid-phase partition cartridges in the determination of fungicideresidues in vegetable samples.J Chromatogr1993 Jul 238360304
Environmental impact of Pyrazophos. 1. Contribution, degradation in plants and in the rat.Environ Qual Saf Suppl19751063720