Acephate

Basic Info

Common NameAcephate(F05023)
2D Structure
Description

Acephate is an organophosphate foliar insecticide of moderate persistence with residual systemic activity of about 10–15 days at the recommended use rate. It is used primarily for control of aphids, including resistant species, in vegetables (e.g. potatoes, carrots, greenhouse tomatoes, and lettuce) and in horticulture (e.g. on roses and greenhouse ornamentals). It also controls leaf miners, caterpillars, sawflies and thrips in the previously stated crops as well as turf, and forestry. By direct application to mounds, it is effective in destroying imported fire ants.

FRCD IDF05023
CAS Number30560-19-1
PubChem CID1982
FormulaC4H10NO3PS
IUPAC Name

N-[methoxy(methylsulfanyl)phosphoryl]acetamide

InChI Key

YASYVMFAVPKPKE-UHFFFAOYSA-N

InChI

InChI=1S/C4H10NO3PS/c1-4(6)5-9(7,8-2)10-3/h1-3H3,(H,5,6,7)

Canonical SMILES

CC(=O)NP(=O)(OC)SC

Isomeric SMILES

CC(=O)NP(=O)(OC)SC

Synonyms
        
            acephate
        
            Orthene
        
            30560-19-1
        
            Acetamidophos
        
            Ortran
        
            Ortril
        
            Acephat
        
            Acetylphosphoramidothioic acid O,S-dimethyl ester
        
            Orthene-755
        
            O,S-Dimethylacetylphosphoroamidothioate
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganophosphorus compounds
ClassOrganothiophosphorus compounds
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentOrganothiophosphorus compounds
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsSulfenyl compound - Organothiophosphorus compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as organothiophosphorus compounds. These are organic derivatives of thiophosphonic acid, thiophosphoric acid, dithiophosphoric acid, or phosphorotrithioic acid, or derivatives thereof. Thiophosphonic acid, dithiophosphoric acid, thiophosphoric acid, and phosphorotrithioic acid are thiophosphorus compounds with the formula OP(O)(=S), OP(S)(=S)O, OP(O)(=S)O, and OP(=S)(S)S, respectively.

Properties

Property NameProperty Value
Molecular Weight183.162
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Complexity172
Monoisotopic Mass183.012
Exact Mass183.012
XLogP-0.8
Formal Charge0
Heavy Atom Count10
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+0.9852
Human Intestinal AbsorptionHIA+0.9313
Caco-2 PermeabilityCaco2-0.5352
P-glycoprotein SubstrateNon-substrate0.9225
P-glycoprotein InhibitorNon-inhibitor0.8962
Non-inhibitor0.9806
Renal Organic Cation TransporterNon-inhibitor0.9710
Distribution
Subcellular localizationMitochondria0.8057
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7973
CYP450 2D6 SubstrateNon-substrate0.8347
CYP450 3A4 SubstrateNon-substrate0.6106
CYP450 1A2 InhibitorNon-inhibitor0.7142
CYP450 2C9 InhibitorNon-inhibitor0.7429
CYP450 2D6 InhibitorNon-inhibitor0.9226
CYP450 2C19 InhibitorNon-inhibitor0.7770
CYP450 3A4 InhibitorNon-inhibitor0.9337
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8779
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9893
Non-inhibitor0.9603
AMES ToxicityNon AMES toxic0.9133
CarcinogensCarcinogens 0.5058
Fish ToxicityHigh FHMT0.7118
Tetrahymena Pyriformis ToxicityLow TPT0.5111
Honey Bee ToxicityHigh HBT0.8862
BiodegradationReady biodegradable0.7562
Acute Oral ToxicityIII0.7787
Carcinogenicity (Three-class)Non-required0.5752
Model Value Unit
Absorption
Aqueous solubility0.4774LogS
Caco-2 Permeability0.8482LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4280LD50, mol/kg
Fish Toxicity1.6181pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.4904pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Wild CabbageThailand5mg/kg
CabbagesCanada0. 3mg/kg
Citrus FruitsThailand5mg/kg
TomatoMalaysia5mg/kg
CauliflowerThailand5mg/kg
PotatoThailand0. 5mg/kg
Brussels SproutsThailand5mg/kg
BroccoliThailand5mg/kg
VegetableItalysee eu mrls
FruitItalysee eu mrls
Hort BrassicaSingapore5mg/kg
PeppersMalaysia5mg/kg
PeelMalaysia1mg/kg
CauliflowerMalaysia2mg/kg
TomatoSingapore5mg/kg
Citrus FruitsSingapore5mg/kg
PotatoSingapore0. 5mg/kg
LettuceSingapore10mg/kg
Stem VegetablesMalaysia1.00 mg/kg
VegetableSwedensee eu mrls

References

TitleJournalDatePubmed ID
Chronic exposure to acephate triggers ROS-mediated injuries at organismal and sub-organismal levels of <i>Drosophila melanogaster</i>.Toxicol Res (Camb)2018 Sep 130310664
Au-Decorated Dragonfly Wing Bioscaffold Arrays as Flexible Surface-Enhanced RamanScattering (SERS) Substrate for Simultaneous Determination of Pesticide Residues.Nanomaterials (Basel)2018 Apr 2829710795
Metabonomic analysis of the protective effect of quercetin on the toxicity induced by mixture of organophosphate pesticides in rat urine.Hum Exp Toxicol2017 May27251765
Photocatalytic degradation of Acephate, Omethoate, and Methyl parathion byFe3O4@SiO2@mTiO2 nanomicrospheres.J Hazard Mater2016 Sep 527152972
Acephate exposure during a perinatal life program to type 2 diabetes.Toxicology2016 Nov 3027765684
Chronic cumulative risk assessment of the exposure to organophosphorus, carbamateand pyrethroid and pyrethrin pesticides through fruit and vegetables consumption in the region of Valencia (Spain).Food Chem Toxicol2016 Mar26774911
Risk assessment of the cumulative acute exposure of Hungarian population toorganophosphorus pesticide residues with regard to consumers of plant basedfoods.Food Chem Toxicol2016 Mar26807885
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
Residue levels and risk assessment of pesticides in nuts of China.Chemosphere2016 Feb26408971
Consumption of fruits and vegetables and probabilistic assessment of thecumulative acute exposure to organophosphorus and carbamate pesticides ofschoolchildren in Slovenia.Public Health Nutr2016 Feb25990202
Glucosinolate Accumulation and Related Gene Expression in Pak Choi (Brassica rapaL. ssp. chinensis var. communis [N. Tsen & S.H. Lee] Hanelt) in Response toInsecticide Application.J Agric Food Chem2015 Nov 1126485123
Liquid chromatography-electrospray ionization tandem mass spectrometry anddynamic multiple reaction monitoring method for determining multiple pesticideresidues in tomato.Food Chem2015 May 1525577051
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
Enantioselective Dissipation of Acephate and Its Metabolite, Methamidophos, during Tea Cultivation, Manufacturing, and Infusion.J Agric Food Chem2015 Feb 425582130
Dissipation behavior and risk assessment of acephate in brinjal using GLC withFPD.Environ Monit Assess2015 Feb25632903
Monitoring of pesticide residues levels in fresh vegetable form Heibei Province, North China.Environ Monit Assess2014 Oct24869955
Thin-layer chromatography/direct analysis in real time time-of-flight massspectrometry and isotope dilution to analyze organophosphorus insecticides infatty foods.J Chromatogr A2014 Nov 2825454149
Metabonomic analysis of the joint toxic action of long-term low-level exposure to a mixture of four organophosphate pesticides in rat plasma.Mol Biosyst2014 May24626741
Acetylcholinesterase based biosensor for monitoring of Malathion and Acephate in food samples: a voltammetric study.Food Chem2014 Jan 124001830
Development of molecularly imprinted electrochemical sensors based onFe3O4@MWNT-COOH/CS nanocomposite layers for detecting traces of acephate andtrichlorfon.Analyst2014 Dec 2125325612

Targets

Target Details

Tissue-type plasminogen activator

General Function:
Serine-type endopeptidase activity
Specific Function:
Converts the abundant, but inactive, zymogen plasminogen to plasmin by hydrolyzing a single Arg-Val bond in plasminogen. By controlling plasmin-mediated proteolysis, it plays an important role in tissue remodeling and degradation, in cell migration and many other physiopathological events. Plays a direct role in facilitating neuronal migration.
Gene Name:
PLAT
Uniprot ID:
P00750
Molecular Weight:
62916.495 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details

Urokinase plasminogen activator surface receptor

General Function:
Urokinase plasminogen activator receptor activity
Specific Function:
Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
Gene Name:
PLAUR
Uniprot ID:
Q03405
Molecular Weight:
36977.62 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]