Basic Info

Common NameOmethoate(F06066)
2D Structure
FRCD IDF06066
CAS Number1113-02-6
PubChem CID14210
FormulaC5H12NO4PS
IUPAC Name

2-dimethoxyphosphorylsulfanyl-N-methylacetamide

InChI Key

PZXOQEXFMJCDPG-UHFFFAOYSA-N

InChI

InChI=1S/C5H12NO4PS/c1-6-5(7)4-12-11(8,9-2)10-3/h4H2,1-3H3,(H,6,7)

Canonical SMILES

CNC(=O)CSP(=O)(OC)OC

Isomeric SMILES

CNC(=O)CSP(=O)(OC)OC

Synonyms
        
            Dimethoate PO isologue
        
            OMETHOATE
        
            Dimethoxon
        
            1113-02-6
        
            Folimat
        
            PO-Dimethoate
        
            Dimethoate O-analog
        
            Omethoat
        
            Dimethoate-met
        
            P=O-Rogor
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassCarboxylic acid derivatives
Intermediate Tree NodesCarboxylic acid amides
Direct ParentSecondary carboxylic acid amides
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsSecondary carboxylic acid amide - Sulfenyl compound - Organothiophosphorus compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as secondary carboxylic acid amides. These are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl).

Properties

Property NameProperty Value
Molecular Weight213.188
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Complexity190
Monoisotopic Mass213.022
Exact Mass213.022
XLogP-0.9
Formal Charge0
Heavy Atom Count12
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+0.9863
Human Intestinal AbsorptionHIA+0.9062
Caco-2 PermeabilityCaco2-0.5670
P-glycoprotein SubstrateNon-substrate0.8044
P-glycoprotein InhibitorNon-inhibitor0.7868
Non-inhibitor0.9725
Renal Organic Cation TransporterNon-inhibitor0.9385
Distribution
Subcellular localizationMitochondria0.6555
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7693
CYP450 2D6 SubstrateNon-substrate0.8122
CYP450 3A4 SubstrateSubstrate0.5371
CYP450 1A2 InhibitorNon-inhibitor0.7804
CYP450 2C9 InhibitorNon-inhibitor0.8005
CYP450 2D6 InhibitorNon-inhibitor0.9212
CYP450 2C19 InhibitorNon-inhibitor0.7411
CYP450 3A4 InhibitorNon-inhibitor0.8385
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9069
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9873
Non-inhibitor0.9354
AMES ToxicityAMES toxic0.6689
CarcinogensNon-carcinogens0.5745
Fish ToxicityLow FHMT0.5938
Tetrahymena Pyriformis ToxicityHigh TPT0.5000
Honey Bee ToxicityHigh HBT0.8539
BiodegradationReady biodegradable0.6385
Acute Oral ToxicityI0.7815
Carcinogenicity (Three-class)Non-required0.7049

Model Value Unit
Absorption
Aqueous solubility-0.3667LogS
Caco-2 Permeability0.3745LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.8206LD50, mol/kg
Fish Toxicity1.4944pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.1707pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Breadfruits (Jackfruits, Other species of genus Artocarpus, not elsewhere mentioned,)0163090European Union0.01*17/01/2018
Head cabbages (Pointed head cabbages, Red cabbages, Savoy cabbages, White cabbage,)0242020European Union0.01*17/01/2018
Others (2)0402990European Union0.01*17/01/2018
Buckwheat and other pseudocereals (Amaranth/kiwicha, Amaranth/kiwicha, Amaranth/kiwicha, Kaniwa/canihua, Quinoa, Chia seeds,)0500020European Union0.01*17/01/2018
Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei...0631030European Union0.05*17/01/2018
Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe...0632010European Union0.05*17/01/2018
Nutmeg (Annatto, Candlenut, Wattleseeds, Calabash nutmeg,)0810090European Union0.05*17/01/2018
Peppercorn (black, green and white) (Brazilian pepper, Cubeb/tailed pepper, Grain of paradise, Long pepper/pipali, Pink pepper, Sumac, West African pepper,)0820060European Union0.05*17/01/2018
TeaJapan1ppm
Other NutsJapan0.1ppm
WalnutJapan0.2ppm
AlmondJapan0.2ppm
PecanJapan0.2ppm
ChestnutJapan0.2ppm
Ginkgo NutJapan0.2ppm
CarrotsKorea0.01ppm
PeanutsKorea0.01ppm
CucumbersKorea0.01ppm
PeasKorea0.01ppm
LettuceKorea0.01ppm

References

TitleJournalDatePubmed ID
Omethoate treatment mitigates high salt stress inhibited maize seed germination.Pestic Biochem Physiol2018 Jan29463412
Probabilistic dietary risk assessment of pesticide residues in foods for theGerman population based on food monitoring data from 2009 to 2014.J Expo Sci Environ Epidemiol2018 Jan28677675
Fluorescence Determination of Omethoate Based on a Dual Strategy for ImprovingSensitivity.J Agric Food Chem2017 Apr 328350464
Quantum dot-DNA aptamer conjugates coupled with capillary electrophoresis: Auniversal strategy for ratiometric detection of organophosphorus pesticides.Talanta201626695234
Colorimetric and Phosphorimetric Dual-Signaling Strategy Mediated by Inner FilterEffect for Highly Sensitive Assay of Organophosphorus Pesticides.J Agric Food Chem2015 Oct 1426411607
Degradation of four organophosphorous pesticides catalyzed by chitosan-metalcoordination complexes.Environ Sci Pollut Res Int2015 Oct26003089
Direct Immersion Solid-Phase Microextraction with Matrix-Compatible Fiber Coatingfor Multiresidue Pesticide Analysis of Grapes by GasChromatography-Time-of-Flight Mass Spectrometry (DI-SPME-GC-ToFMS).J Agric Food Chem2015 May 1325856792
Monitoring of pesticide residues levels in fresh vegetable form Heibei Province, North China.Environ Monit Assess2014 Oct24869955
Organophosphorus pesticides detection using broad-specific single-stranded DNAbased fluorescence polarization aptamer assay.Biosens Bioelectron2014 May 1524384262
Organophosphorus pesticide residues in vegetables from farms, markets, and asupermarket around Kwan Phayao Lake of Northern Thailand.Arch Environ Contam Toxicol2014 Jul24609615
Pesticide residues in cashew apple, guava, kaki and peach: GC-μECD, GC-FPD andLC-MS/MS multiresidue method validation, analysis and cumulative acute riskassessment.Food Chem2014 Dec 124996324
Development of a single aptamer-based surface enhanced Raman scattering methodfor rapid detection of multiple pesticides.Analyst2014 Apr 2124551875
Ensuring selectivity and sensitivity by timed- and ultra-selective reactionmonitoring during gas chromatography-tandem mass spectrometric determination ofpesticides.J Chromatogr A2013 Nov 2924161146
Dispersive microextraction based on "magnetic water" coupled to gaschromatography/mass spectrometry for the fast determination of organophosphoruspesticides in cold-pressed vegetable oils.J Agric Food Chem2013 Jun 523687955
Pesticide residues in market foods in Shaanxi Province of China in 2010.Food Chem2013 Jun 123411338
Computational and experimental investigation of molecular imprinted polymers for selective extraction of dimethoate and its metabolite omethoate from olive oil.J Chromatogr A2013 Jan 2523290360
Simultaneous determination of nine trace organophosphorous pesticide residues in fruit samples using molecularly imprinted matrix solid-phase dispersion followed by gas chromatography.J Agric Food Chem2013 Apr 2423544352
Selection of DNA aptamers that bind to four organophosphorus pesticides.Biotechnol Lett2012 May22261866
Chromogenic platform based on recombinant Drosophila melanogasteracetylcholinesterase for visible unidirectional assay of organophosphate andcarbamate insecticide residues.Anal Chim Acta2012 Mar 3022365130
Reduction of pesticide residues on fresh vegetables with electrolyzed watertreatment.J Food Sci2011 May22420563