Chlorpyrifos-Methyl

Basic Info

Common NameChlorpyrifos-Methyl(F05041)
2D Structure
Description

Chlorpyrifos-methyl is a pyridine organothiophosphate insecticide. It is a general use organophosphate insecticide registered in 1985 for use on stored grain (for protection of stored food, feed oil, and seed grains against injury from stored grain weevils, moths, borers, beetles and mealworms including granary weevil, rice weevil, red flour beetle, confused flour beetle, saw-toothed grain beetle, Indian meal moth, and Angoumois grain moth, lessor grain borers), seed treatment, grain bin and warehouse. Chlorpyrifos-methyl can cause cholinesterase inhibition in humans; that is, it can overstimulate the nervous system causing nausea, dizziness, confusion, and at very high exposures (e.g., accidents or major spills), respiratory paralysis and death. In addition, systemic toxicity may include body weight loss, decreased food consumption, liver, kidney and adrenal pathology.

FRCD IDF05041
CAS Number5598-13-0
PubChem CID21803
FormulaC7H7Cl3NO3PS
IUPAC Name

dimethoxy-sulfanylidene-(3,5,6-trichloropyridin-2-yl)oxy-$l^{5}-phosphane

InChI Key

HRBKVYFZANMGRE-UHFFFAOYSA-N

InChI

InChI=1S/C7H7Cl3NO3PS/c1-12-15(16,13-2)14-7-5(9)3-4(8)6(10)11-7/h3H,1-2H3

Canonical SMILES

COP(=S)(OC)OC1=NC(=C(C=C1Cl)Cl)Cl

Isomeric SMILES

COP(=S)(OC)OC1=NC(=C(C=C1Cl)Cl)Cl

Synonyms
        
            Methyl chlorpyrifos
        
            Chlorpyrifos-methyl
        
            Trichlormethylfos
        
            Chloropyriphos-methyl
        
            5598-13-0
        
            Reldan
        
            Methyl chlorpyriphos
        
            Noltran
        
            Zertell
        
            Dursban methyl
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 heteromonocyclic compounds
SubstituentsAryl thiophosphate - Thiophosphate triester - Polyhalopyridine - 2-halopyridine - Aryl chloride - Aryl halide - Pyridine - Heteroaromatic compound - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic oxygen compound - Aromatic heteromonocyclic 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 Weight322.521
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Complexity278
Monoisotopic Mass320.895
Exact Mass320.895
XLogP4.3
Formal Charge0
Heavy Atom Count16
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+0.9688
Human Intestinal AbsorptionHIA+0.9910
Caco-2 PermeabilityCaco2+0.5264
P-glycoprotein SubstrateNon-substrate0.8898
P-glycoprotein InhibitorNon-inhibitor0.8451
Non-inhibitor1.0000
Renal Organic Cation TransporterNon-inhibitor0.9190
Distribution
Subcellular localizationMitochondria0.7179
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7276
CYP450 2D6 SubstrateSubstrate0.5365
CYP450 3A4 SubstrateSubstrate0.6166
CYP450 1A2 InhibitorInhibitor0.5584
CYP450 2C9 InhibitorNon-inhibitor0.7094
CYP450 2D6 InhibitorNon-inhibitor0.9022
CYP450 2C19 InhibitorInhibitor0.5625
CYP450 3A4 InhibitorNon-inhibitor0.7104
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6963
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9517
Non-inhibitor0.8640
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.7984
Fish ToxicityHigh FHMT0.6405
Tetrahymena Pyriformis ToxicityHigh TPT0.7763
Honey Bee ToxicityHigh HBT0.8779
BiodegradationNot ready biodegradable0.9484
Acute Oral ToxicityIII0.8165
Carcinogenicity (Three-class)Non-required0.6787
Model Value Unit
Absorption
Aqueous solubility-4.7575LogS
Caco-2 Permeability1.2235LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2781LD50, mol/kg
Fish Toxicity1.7105pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3775pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Others (2)0130990European Union0.506/02/2018
Fat1017020European Union0.05*06/02/2018
Celeriacs/turnip rooted celeries0213030European Union0.05*06/02/2018
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.05*06/02/2018
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.506/02/2018
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.306/02/2018
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.05*06/02/2018
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union106/02/2018
Others (2)0110990European Union0.05*06/02/2018
Tree nuts0120000European Union0.05*06/02/2018
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.05*06/02/2018
Brazil nuts0120020European Union0.05*06/02/2018
Cashew nuts0120030European Union0.05*06/02/2018
Chestnuts0120040European Union0.05*06/02/2018
Coconuts (Areca nuts/betel nuts,)0120050European Union0.05*06/02/2018
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.05*06/02/2018
Macadamias0120070European Union0.05*06/02/2018
Pecans (Hickory nuts,)0120080European Union0.05*06/02/2018
Pistachios0120100European Union0.05*06/02/2018
Walnuts0120110European Union0.05*06/02/2018

References

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Dissipation of chlorantraniliprole, chlorpyrifos-methyl andindoxacarb-insecticides used to control codling moth (Cydia Pomonella L.) andleafrollers (Tortricidae) in apples for production of baby food.Environ Sci Pollut Res Int2017 May28349309
Terahertz sensing of chlorpyrifos-methyl using metamaterials.Food Chem2017 Mar 127719917
Monitoring of Pesticide Residues in Commonly Used Fruits and Vegetables inKuwait.Int J Environ Res Public Health2017 Jul 2528757570
Impact of substrate contamination with mycotoxins, heavy metals and pesticides on the growth performance and composition of black soldier fly larvae (Hermetia illucens) for use in the feed and food value chain.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017 Aug28278126
Chlorpyrifos-methyl solubilisation by humic acids used as bio-surfactants extracted from lignocelluloses and kitchen wastes.Chemosphere2016 Sep27289207
The potency of Saccharomyces cerevisiae and Lactobacillus plantarum to dissipate organophosphorus pesticides in wheat during fermentation.J Food Sci Technol2016 Dec28115761
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Susceptibility of nine organophosphorus pesticides in skimmed milk towardsinoculated lactic acid bacteria and yogurt starters.J Sci Food Agric2015 Jan24777955
HPLC-MS/MS method for the measurement of insecticide degradates in baby food.J Agric Food Chem2014 Jul 2324910900
Pesticide residue analysis in cereal-based baby foods using multi-walled carbonnanotubes dispersive solid-phase extraction.Anal Bioanal Chem2012 Jul22623047
Pesticide analysis in toasted barley and chickpea flours.J Sep Sci2012 Jan25940740
A pilot study of pesticides and PCBs in the breast milk of women residing inurban and agricultural communities of California.J Environ Monit2011 Nov22009134
Effect of bromine oxidation on high-performance thin-layer chromatographymulti-enzyme inhibition assay detection of organophosphates and carbamateinsecticides.J Chromatogr A2011 May 1321397236
Genetic variability in esterases and the insecticide resistance in brazilianstrains of Oryzaephilus mercator and Oryzaephilus surinamensis (Coleoptera:Silvanidae).Bull Entomol Res2011 Apr21034518
Pesticide residues in dried table grapes from the Aegean region of Turkey.Environ Monit Assess2010 Aug19533395
Impact of food consumption habits on the pesticide dietary intake: comparisonbetween a French vegetarian and the general population.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2009Oct19707917
Levels of metabolites of organophosphate pesticides, phthalates, and bisphenol A in pooled urine specimens from pregnant women participating in the NorwegianMother and Child Cohort Study (MoBa).Int J Hyg Environ Health2009 Sep19394271
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