Pirimiphos-Methyl

Basic Info

Common NamePirimiphos-Methyl(F05432)
2D Structure
Description

Pirimiphos-methyl is an organophosphate and fumigant insecticide with pirimiphos-methyl and no longer in production. It is used to control a wide range of insects and mites in stores, animal houses, domestic and industrial premisies. It is considered to be an acetylcholinesterase (AChE) inhibitor with contact and respiratory action. This is one of several compounds used for vector control of Triatoma.

FRCD IDF05432
CAS Number29232-93-7
PubChem CID34526
FormulaC11H20N3O3PS
IUPAC Name

4-dimethoxyphosphinothioyloxy-N,N-diethyl-6-methylpyrimidin-2-amine

InChI Key

QHOQHJPRIBSPCY-UHFFFAOYSA-N

InChI

InChI=1S/C11H20N3O3PS/c1-6-14(7-2)11-12-9(3)8-10(13-11)17-18(19,15-4)16-5/h8H,6-7H2,1-5H3

Canonical SMILES

CCN(CC)C1=NC(=CC(=N1)OP(=S)(OC)OC)C

Isomeric SMILES

CCN(CC)C1=NC(=CC(=N1)OP(=S)(OC)OC)C

Synonyms
        
            Pirimiphos-methyl
        
            PIRIMIPHOS METHYL
        
            29232-93-7
        
            Pyrimiphos methyl
        
            Pirimifosmethyl
        
            Actellic
        
            Actellifog
        
            Actelic
        
            Silosan
        
            Methylpirimiphos
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 NodesAryl thiophosphates
Direct ParentPyrimidinyl phosphorothioates
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPyrimidinyl phosphorothioate - Dialkylarylamine - Thiophosphate triester - Aminopyrimidine - Pyrimidine - Heteroaromatic compound - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom.

Properties

Property NameProperty Value
Molecular Weight305.333
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Complexity310
Monoisotopic Mass305.096
Exact Mass305.096
XLogP4.2
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+0.9724
Human Intestinal AbsorptionHIA+0.9683
Caco-2 PermeabilityCaco2-0.5344
P-glycoprotein SubstrateNon-substrate0.6736
P-glycoprotein InhibitorNon-inhibitor0.7047
Non-inhibitor0.9958
Renal Organic Cation TransporterNon-inhibitor0.8490
Distribution
Subcellular localizationMitochondria0.4777
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7663
CYP450 2D6 SubstrateNon-substrate0.7607
CYP450 3A4 SubstrateSubstrate0.5143
CYP450 1A2 InhibitorNon-inhibitor0.5445
CYP450 2C9 InhibitorNon-inhibitor0.6550
CYP450 2D6 InhibitorNon-inhibitor0.8907
CYP450 2C19 InhibitorNon-inhibitor0.5457
CYP450 3A4 InhibitorNon-inhibitor0.8319
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8729
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8932
Non-inhibitor0.7347
AMES ToxicityNon AMES toxic0.6446
CarcinogensNon-carcinogens0.7470
Fish ToxicityLow FHMT0.8268
Tetrahymena Pyriformis ToxicityHigh TPT0.6147
Honey Bee ToxicityHigh HBT0.8062
BiodegradationNot ready biodegradable0.9881
Acute Oral ToxicityIII0.8088
Carcinogenicity (Three-class)Non-required0.5979
Model Value Unit
Absorption
Aqueous solubility-3.5708LogS
Caco-2 Permeability1.0382LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4191LD50, mol/kg
Fish Toxicity1.7309pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3088pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
BeansNew Zealand0. 2mg/kg
Citrus FruitsNew Zealand1mg/kg
Kiwi FruitNew Zealand2mg/kg
PersimmonNew Zealand0. 5mg/kg
Others (2)0212990European Union0.01*09/08/2016
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.01*09/08/2016
Citrus fruits0110000European Union0.01*09/08/2016
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*09/08/2016
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*09/08/2016
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*09/08/2016
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01*09/08/2016
Others (2)0110990European Union0.01*09/08/2016
Tree nuts0120000European Union0.01*09/08/2016
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.01*09/08/2016
Brazil nuts0120020European Union0.01*09/08/2016
Cashew nuts0120030European Union0.01*09/08/2016
Chestnuts0120040European Union0.01*09/08/2016
Coconuts (Areca nuts/betel nuts,)0120050European Union0.01*09/08/2016
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.01*09/08/2016
Macadamias0120070European Union0.01*09/08/2016

References

TitleJournalDatePubmed ID
Simultaneous determination of organophosphorus pesticides and phthalates in baby food samples by ultrasound-vortex-assisted liquid-liquid microextraction andGC-IT/MS.Anal Bioanal Chem2018 May29549507
Preparation and application of chlorpyrifos molecularly imprinted solid-phasemicroextraction probes for the residual determination of organophosphorouspesticides in fresh and dry foods.J Sep Sci2018 Jun 729878613
Pesticide residues in raw and processed maize grains and flour from selectedareas in Dar es Salaam and Ruvuma, Tanzania.Chemosphere2017 Oct28688847
In vitro toxicity of pirimiphos-methyl in Atlantic salmon hepatocytes.Toxicol In Vitro2017 Mar27845199
Comprehensive strategy for pesticide residue analysis through the productioncycle of gilthead sea bream and Atlantic salmon.Chemosphere2017 Jul28371708
Dissipation kinetics of organophosphorus pesticides in milled toasted maize andwheat flour (gofio) during storage.Food Chem2017 Aug 1528372254
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
Residue levels of five grain-storage-use insecticides during the productionprocess of sorghum distilled spirits.Food Chem2016 Sep 127041292
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
Chronic dietary exposure to pesticide residues and associated risk in the French ELFE cohort of pregnant women.Environ Int2016 Jul-Aug27187793
Degradation of bifenthrin and pirimiphos-methyl residues in stored wheat grains(Triticum aestivum L.) by ozonation.Food Chem2016 Jul 1526948611
Combining electrostatic powder with an insecticide: effect on stored-productbeetles and on the commodity.Pest Manag Sci2016 Dec26864880
The potency of Saccharomyces cerevisiae and Lactobacillus plantarum to dissipate organophosphorus pesticides in wheat during fermentation.J Food Sci Technol2016 Dec28115761
Biosensor based on electrospun blended chitosan-poly (vinyl alcohol) nanofibrous enzymatically sensitized membranes for pirimiphos-methyl detection in olive oil.Talanta2016 Aug 127216682
Challenging conventional risk assessment with respect to human exposure to multiple food contaminants in food: A case study using maize.Toxicol Lett2015 Oct 126196220
Susceptibility of nine organophosphorus pesticides in skimmed milk towardsinoculated lactic acid bacteria and yogurt starters.J Sci Food Agric2015 Jan24777955
Risk assessment of bearded vulture (Gypaetus barbatus) exposure to topicalantiparasitics used in livestock within an ecotoxicovigilance framework.Sci Total Environ2015 Dec 126254071
Decrease of pirimiphos-methyl and deltamethrin residues in stored rice withpost-harvest treatment.Int J Environ Res Public Health2014 May 1624840352
Comparison of the effect of insecticides on three strains of Tyrophagus putrescentiae (Acari: Astigmata) using an impregnated filter paper test and a growth test.Pest Manag Sci2014 Jul24115485
Pesticide residues in grain from Kazakhstan and potential health risks associatedwith exposure to detected pesticides.Food Chem Toxicol2014 Feb24316210