Basic Info

Common NamePymetrozine(F05129)
2D Structure
Description

Pymetrozine is a neuroactive insecticide that selectively affects chordotonal mechanoreceptors. Physiologically, it appears to act by preventing these insects from inserting their stylus into the plant tissue. It controls many strains of aphids on potatoes and in a range of vegetable brassica crops. Pymetrozine has been determined to be of low acute toxicity to humans, birds, aquatic organisms, mammals, and bees.

FRCD IDF05129
CAS Number123312-89-0
PubChem CID9576037
FormulaC10H11N5O
IUPAC Name

6-methyl-4-[(E)-pyridin-3-ylmethylideneamino]-2,5-dihydro-1,2,4-triazin-3-one

InChI Key

QHMTXANCGGJZRX-WUXMJOGZSA-N

InChI

InChI=1S/C10H11N5O/c1-8-7-15(10(16)14-13-8)12-6-9-3-2-4-11-5-9/h2-6H,7H2,1H3,(H,14,16)/b12-6+

Canonical SMILES

CC1=NNC(=O)N(C1)N=CC2=CN=CC=C2

Isomeric SMILES

CC1=NNC(=O)N(C1)/N=C/C2=CN=CC=C2

Synonyms
        
            Pymetrozine
        
            123312-89-0
        
            Chess
        
            Endeavor
        
            Pymetrozin
        
            Fulfill
        
            Plenum
        
            CGA 215944
        
            UNII-F0G3V7874J
        
            HSDB 7054
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassTriazines
Subclass1,2,4-triazines
Intermediate Tree NodesNot available
Direct Parent1,2,4-triazines
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
Substituents1,2,4-triazine - Pyridine - Heteroaromatic compound - Azacycle - 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 1,2,4-triazines. These are compounds containing a triazine ring, which is a heterocyclic ring, similar to the six-member benzene ring but with three carbons replaced by nitrogen atoms, at ring positions 1, 2, and 4.

Properties

Property NameProperty Value
Molecular Weight217.232
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Complexity325
Monoisotopic Mass217.096
Exact Mass217.096
XLogP0
Formal Charge0
Heavy Atom Count16
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9455
Human Intestinal AbsorptionHIA+0.9957
Caco-2 PermeabilityCaco2+0.5612
P-glycoprotein SubstrateNon-substrate0.5627
P-glycoprotein InhibitorNon-inhibitor0.7145
Non-inhibitor0.9767
Renal Organic Cation TransporterNon-inhibitor0.6137
Distribution
Subcellular localizationMitochondria0.7928
Metabolism
CYP450 2C9 SubstrateNon-substrate0.5731
CYP450 2D6 SubstrateNon-substrate0.7986
CYP450 3A4 SubstrateSubstrate0.5836
CYP450 1A2 InhibitorInhibitor0.5229
CYP450 2C9 InhibitorNon-inhibitor0.7997
CYP450 2D6 InhibitorNon-inhibitor0.9257
CYP450 2C19 InhibitorNon-inhibitor0.7743
CYP450 3A4 InhibitorNon-inhibitor0.9092
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8285
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7510
Non-inhibitor0.7971
AMES ToxicityAMES toxic0.5175
CarcinogensNon-carcinogens0.8885
Fish ToxicityHigh FHMT0.6842
Tetrahymena Pyriformis ToxicityHigh TPT0.9275
Honey Bee ToxicityLow HBT0.8681
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.6702
Carcinogenicity (Three-class)Non-required0.6160

Model Value Unit
Absorption
Aqueous solubility-2.2252LogS
Caco-2 Permeability1.1744LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4775LD50, mol/kg
Fish Toxicity2.0199pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4705pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
HopBritain15mg/kg
TeaBritain0.1mg/kg
Ware PotatoesBritain0.02mg/kg
Early PotatoesBritain0.02mg/kg
Other OilseedsBritain0.02mg/kg
Hemp SeedBritain0.02mg/kg
Cotton SeedBritain0.05mg/kg
Mustard SeedBritain0.02mg/kg
Soya BeanBritain0.02mg/kg
Rape SeedBritain0.02mg/kg
Sunflower SeedBritain0.02mg/kg
Sesame SeedBritain0.02mg/kg
Poppy SeedBritain0.02mg/kg
PeanutsBritain0.02mg/kg
BorageBritain0.02mg/kg
LinseedBritain0.02mg/kg
Other PulsesBritain0.02mg/kg
LupinsBritain0.02mg/kg
PeasBritain0.02mg/kg
LentilsBritain0.02mg/kg

References

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Occurrence of commonly used pesticides in personal air samples and theirassociated health risk among paddy farmers.Sci Total Environ2017 Dec 1528633115
Phage-mediated dissemination of virulence factors in pathogenic bacteriafacilitated by antibiotic growth promoters in animals: a perspective.Anim Health Res Rev2017 Dec29183407
Phylodynamics of foot-and-mouth disease virus O/PanAsia in Vietnam 2010-2014.Vet Res2017 Apr 1328403902
Star Anise (Illicium verum Hook. f.) as Quorum Sensing and Biofilm FormationInhibitor on Foodborne Bacteria: Study in Milk.J Food Prot2017 Apr28294685
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Prevalence of the Antibiotic Resistance Genes in Coagulase-Positive-andNegative-Staphylococcus in Chicken Meat Retailed to Consumers.Front Microbiol2016 Nov 2227920760
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What Can We Learn from a Metagenomic Analysis of a Georgian BacteriophageCocktail?Viruses2015 Dec 1226703713
Effect of insecticide-treated potato plants on aphid behavior and potato virus Y acquisition.Pest Manag Sci2015 Aug25159012
Phytomelatonin: assisting plants to survive and thrive.Molecules2015 Apr 2225911967
A matrix sensitive gas chromatography method for the analysis of pymetrozine inred pepper: application to dissipation pattern and PHRL.Food Chem2014 Mar 124176366
Effect of new and old pesticides on Orius armatus (Gross) - an Australian predator of western flower thrips, Frankliniella occidentalis (Pergande).Pest Manag Sci2014 Mar23616278
Thiourea, a ROS scavenger, regulates source-to-sink relationship to enhance crop yield and oil content in Brassica juncea (L.).PLoS One2013 Sep 1824058504
Reduction of hazardous organic solvent in sample preparation for hydrophilicpesticide residues in agricultural products with conventional liquidchromatography.J Agric Food Chem2013 May 2223614723