Phosmet

Basic Info

Common NamePhosmet(F05777)
2D Structure
FRCD IDF05777
CAS Number732-11-6
PubChem CID12901
FormulaC11H12NO4PS2
IUPAC Name

2-(dimethoxyphosphinothioylsulfanylmethyl)isoindole-1,3-dione

InChI Key

LMNZTLDVJIUSHT-UHFFFAOYSA-N

InChI

InChI=1S/C11H12NO4PS2/c1-15-17(18,16-2)19-7-12-10(13)8-5-3-4-6-9(8)11(12)14/h3-6H,7H2,1-2H3

Canonical SMILES

COP(=S)(OC)SCN1C(=O)C2=CC=CC=C2C1=O

Isomeric SMILES

COP(=S)(OC)SCN1C(=O)C2=CC=CC=C2C1=O

Synonyms
        
            Phosmet
        
            Fosmet
        
            Decemthion
        
            Phthalophos
        
            732-11-6
        
            Imidathion
        
            Percolate
        
            Prolate
        
            IMIDAN
        
            Ftalophos
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassIsoindoles and derivatives
SubclassIsoindolines
Intermediate Tree NodesIsoindolones
Direct ParentPhthalimides
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsPhthalimide - Isoindole - Carboxylic acid imide, n-substituted - Dithiophosphate s-ester - Benzenoid - Dithiophosphate o-ester - Carboxylic acid imide - Organic dithiophosphate - Carboxylic acid derivative - Sulfenyl compound - Organothiophosphorus compound - Azacycle - Organic oxide - Organopnictogen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phthalimides. These are aromatic heterocyclic compounds containing a 1,3-dioxoisoindoline moiety. They are imide derivatives of phthalic anhydrides.

Properties

Property NameProperty Value
Molecular Weight317.314
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Complexity399
Monoisotopic Mass316.995
Exact Mass316.995
XLogP2.8
Formal Charge0
Heavy Atom Count19
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+0.9686
Human Intestinal AbsorptionHIA+0.9207
Caco-2 PermeabilityCaco2-0.5371
P-glycoprotein SubstrateNon-substrate0.7969
P-glycoprotein InhibitorNon-inhibitor0.8782
Non-inhibitor0.8741
Renal Organic Cation TransporterNon-inhibitor0.8602
Distribution
Subcellular localizationMitochondria0.5497
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7998
CYP450 2D6 SubstrateNon-substrate0.8069
CYP450 3A4 SubstrateSubstrate0.5553
CYP450 1A2 InhibitorNon-inhibitor0.5500
CYP450 2C9 InhibitorNon-inhibitor0.7310
CYP450 2D6 InhibitorNon-inhibitor0.8743
CYP450 2C19 InhibitorNon-inhibitor0.5057
CYP450 3A4 InhibitorNon-inhibitor0.5243
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7113
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9674
Non-inhibitor0.7765
AMES ToxicityAMES toxic0.9107
CarcinogensNon-carcinogens0.7780
Fish ToxicityHigh FHMT0.8942
Tetrahymena Pyriformis ToxicityHigh TPT0.8969
Honey Bee ToxicityHigh HBT0.8356
BiodegradationReady biodegradable0.6285
Acute Oral ToxicityII0.7761
Carcinogenicity (Three-class)Non-required0.6759
Model Value Unit
Absorption
Aqueous solubility-4.0375LogS
Caco-2 Permeability0.8902LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.5661LD50, mol/kg
Fish Toxicity1.5570pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2878pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Pig,FatJapan0.2ppm
Kidney1015040European Union0.130/07/2014
(f) poultry (Bobwhite quail, Chicken (including silkie chicken), Collared Dove, Duck, Geese, Green peafowl, Guinea fowl, Japanese quail, Muskovy duck, Mute swan, Partridge, Peafowl, Pheasant, Pigeo...1016000European Union0.130/07/2014
Kidney1016040European Union0.130/07/2014
Liver1016030European Union0.130/07/2014
Edible offals (other than liver and kidney)1015050European Union0.130/07/2014
Others (2)1015990European Union0.130/07/2014
Muscle1016010European Union0.130/07/2014
Fat1016020European Union0.130/07/2014
Edible offals (other than liver and kidney)1016050European Union0.130/07/2014
Others (2)1016990European Union0.130/07/2014
(g) other farmed terrestrial animals (Alpaca, Bactrian camel, Capybara, Cottontail/American rabbit, Dromedary, Eland, Elk/moose, Emu, Fallow deer, Guinea pig, Hare (farmed), Llama, Nandu/greater rh...1017000European Union0.130/07/2014
Muscle1017010European Union0.130/07/2014
Fat1017020European Union0.130/07/2014
Liver1017030European Union0.130/07/2014
Kidney1017040European Union0.130/07/2014
Edible offals (other than liver and kidney)1017050European Union0.130/07/2014
Others (2)1017990European Union0.130/07/2014
Milk1020000European Union0.05*30/07/2014
Cattle (Species listed with code numbers 1012000-xxx,)1020010European Union0.05*30/07/2014

References

TitleJournalDatePubmed ID
Residual degradation and toxicity of insecticides against Bactrocera oleae.Environ Sci Pollut Res Int2018 Jan29047054
Evaluation of the Penetration of Multiple Classes of Pesticides in Fresh Produce Using Surface-Enhanced Raman Scattering Mapping.J Food Sci2016 Oct 627711977
Ultra-sensitive biosensor based on genetically engineered acetylcholinesteraseimmobilized in poly (vinyl alcohol)/Fe-Ni alloy nanocomposite for phosmetdetection in olive oil.Food Chem2016 Jul 1526948591
Multiresidue method for the quantitation of 20 pesticides in aquatic products.Anal Bioanal Chem2015 Dec26466578
A virulent phage infecting Lactococcus garvieae, with homology to Lactococcuslactis phages.Appl Environ Microbiol2015 Dec26407890
Use of graphene and gold nanorods as substrates for the detection of pesticidesby surface enhanced Raman spectroscopy.J Agric Food Chem2014 Oct 2925317673
Community air monitoring for pesticides-part 2: multiresidue determination ofpesticides in air by gas chromatography, gas chromatography-mass spectrometry,and liquid chromatography-mass spectrometry.Environ Monit Assess2014 Mar24370860
Surface plasmon resonance sensor for phosmet of agricultural products at the ppt detection level.J Agric Food Chem2013 Mar 2023402473
Unexpected chirality of nanoparticle dimers and ultrasensitive chiroplasmonic bioanalysis.J Am Chem Soc2013 Dec 1124246036
Predictors of exposure to organophosphate pesticides in schoolchildren in theProvince of Talca, Chile.Environ Int2012 Oct 1522732215
Determination of some organophosphorus pesticides in water and watermelon samplesby microextraction prior to high-performance liquid chromatography.J Sep Sci2011 Nov22038851
Field evaluation of reduced insecticide spray programs for managing plumcurculio, Conotrachelus nenuphar (Coleoptera: Curculionidae), in Alabama peaches.Pest Manag Sci2011 Jun21268230
Activity of broad-spectrum and reduced-risk insecticides on various life stages of cranberry fruitworm (Lepidoptera: Pyralidae) in highbush blueberry.J Econ Entomol2010 Oct21061972
Harvestman (Opiliones) fauna associated with Maine lowbush blueberry fields inthe major production areas of Washington and Hancock counties.Environ Entomol2010 Oct22546437
Use of ultra-high-pressure liquid chromatography-quadrupole time-of-flight MS to discover the presence of pesticide metabolites in food samples.J Sep Sci2009 Jul19569104
Dialkylphosphates (DAPs) in fruits and vegetables may confound biomonitoring inorganophosphorus insecticide exposure and risk assessment.J Agric Food Chem2008 Nov 2618947233
Decreasing Enterobacter sakazakii (Cronobacter spp.) food contamination levelwith bacteriophages: prospects and problems.Microb Biotechnol2008 Nov21261874
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
Effects of postharvest preparation on organophosphate insecticide residues inapples.J Agric Food Chem2008 Feb 1318173242
Microbial degradation of phosmet on blueberry fruit and in aqueous systems byindigenous bacterial flora on lowbush blueberries (Vaccinium angustifolium).J Food Sci2007 Oct17995608