Etofenprox

Basic Info

Common NameEtofenprox(F05812)
2D Structure
FRCD IDF05812
CAS Number80844-07-1
PubChem CID71245
FormulaC25H28O3
IUPAC Name

1-ethoxy-4-[2-methyl-1-[(3-phenoxyphenyl)methoxy]propan-2-yl]benzene

InChI Key

YREQHYQNNWYQCJ-UHFFFAOYSA-N

InChI

InChI=1S/C25H28O3/c1-4-27-22-15-13-21(14-16-22)25(2,3)19-26-18-20-9-8-12-24(17-20)28-23-10-6-5-7-11-23/h5-17H,4,18-19H2,1-3H3

Canonical SMILES

CCOC1=CC=C(C=C1)C(C)(C)COCC2=CC(=CC=C2)OC3=CC=CC=C3

Isomeric SMILES

CCOC1=CC=C(C=C1)C(C)(C)COCC2=CC(=CC=C2)OC3=CC=CC=C3

Synonyms
        
            Etofenprox
        
            Ethofenprox
        
            80844-07-1
        
            Ethophenprox
        
            1-((2-(4-Ethoxyphenyl)-2-methylpropoxy)methyl)-3-phenoxybenzene
        
            Trebon
        
            Etofenprox [INN]
        
            Etofenproxum [Latin]
        
            2-(4-Ethoxyphenyl)-2-methylpropyl 3-phenoxybenzyl ether
        
            UNII-0LD7P9153C
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassDiphenylethers
Intermediate Tree NodesNot available
Direct ParentDiphenylethers
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsDiphenylether - Diaryl ether - Phenylpropane - Benzylether - Phenoxy compound - Phenol ether - Alkyl aryl ether - Ether - Dialkyl ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Properties

Property NameProperty Value
Molecular Weight376.496
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count9
Complexity422
Monoisotopic Mass376.204
Exact Mass376.204
XLogP7
Formal Charge0
Heavy Atom Count28
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+0.9225
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7690
P-glycoprotein SubstrateSubstrate0.6265
P-glycoprotein InhibitorInhibitor0.7493
Non-inhibitor0.5960
Renal Organic Cation TransporterNon-inhibitor0.7793
Distribution
Subcellular localizationMitochondria0.7293
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8194
CYP450 2D6 SubstrateNon-substrate0.8237
CYP450 3A4 SubstrateSubstrate0.6115
CYP450 1A2 InhibitorInhibitor0.5739
CYP450 2C9 InhibitorNon-inhibitor0.5444
CYP450 2D6 InhibitorNon-inhibitor0.8648
CYP450 2C19 InhibitorNon-inhibitor0.5835
CYP450 3A4 InhibitorNon-inhibitor0.8106
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5860
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9195
Non-inhibitor0.6719
AMES ToxicityNon AMES toxic0.9371
CarcinogensCarcinogens 0.5118
Fish ToxicityHigh FHMT0.8458
Tetrahymena Pyriformis ToxicityHigh TPT0.8529
Honey Bee ToxicityHigh HBT0.8206
BiodegradationNot ready biodegradable0.9708
Acute Oral ToxicityIV0.6374
Carcinogenicity (Three-class)Non-required0.4520
Model Value Unit
Absorption
Aqueous solubility-6.1565LogS
Caco-2 Permeability1.4500LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity0.9759LD50, mol/kg
Fish Toxicity0.7665pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.3342pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MelonsJapan2ppm
Other NutsJapan0.1ppm
WalnutJapan0.1ppm
AlmondJapan0.1ppm
PecanJapan0.1ppm
Ginkgo NutJapan0.1ppm
Passion FruitJapan2ppm
MangoJapan2ppm
GuavaJapan2ppm
PineappleJapan2ppm
AvocadoJapan2ppm
PapayaJapan2ppm
KiwifruitJapan0.2ppm
BananaJapan2ppm
NectarineJapan2ppm
LoquatJapan1ppm
QuinceJapan2ppm
Bamboo ShootsJapan0.5ppm
SpinachJapan2ppm
Other Cucurbitaceous VegetablesJapan2ppm

References

TitleJournalDatePubmed ID
Decline patterns and risk assessment of 10 multi-class pesticides in young sproutamaranth (Amaranthus mangostanus) under greenhouse growing conditions.Environ Sci Pollut Res Int2017 Nov28918593
Comparison of green sample preparation techniques in the analysis of pyrethrinsand pyrethroids in baby food by liquid chromatography-tandem mass spectrometry.J Chromatogr A2017 May 1228372842
Fipronil washoff to municipal wastewater from dogs treated with spot-on products.Sci Total Environ2017 Dec 128505888
Highly sensitive quantification of pyrethroid insecticide etofenprox invegetables with high-performance liquid chromatography and fluorescencedetection.J Chromatogr A2015 Mar 1325662063
Dissipation and Removal of the Etofenprox Residue during Processing in SpringOnion.J Agric Food Chem2015 Aug 526168318
The impact of insecticides applied in apple orchards on the predatory miteKampimodromus aberrans (Acari: Phytoseiidae).Exp Appl Acarol2014 Mar24114337
Estimation of etofenprox residues in tomato fruits by QuEChERS methodology andHPLC-DAD.Bull Environ Contam Toxicol2012 Jun22476259
Insecticide susceptibility of Nezara viridula (Heteroptera: Pentatomidae) andthree other stink bug species composing a soybean pest complex in Japan.J Econ Entomol2012 Jun22812144
Aerobic versus Anaerobic Microbial Degradation of Etofenprox in a California ricefield soil.J Agric Food Chem2011 Mar 2321351774
Soil and glass surface photodegradation of etofenprox under simulated california rice growing conditions.J Agric Food Chem2011 Jul 2721675771
Acute toxicity of chlorantraniliprole to non-target crayfish (Procambarus clarkii) associated with rice-crayfish cropping systems.Pest Manag Sci2010 Sep20730992
Acute toxicity to zebrafish of two organophosphates and four pyrethroids andtheir binary mixtures.Pest Manag Sci2010 Jan19728319
Contamination of rice by etofenprox, diethyl phthalate and alkylphenols: effects on first delivery and sperm count in mice.J Toxicol Sci2010 Feb20118624
Exposure to pesticides residues from consumption of Italian blood oranges.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2009Jul19680977
Development of certified reference material for quantification of two pesticides in brown rice.J Agric Food Chem2009 Sep 2319702268
Determination of pesticides in apples by liquid chromatography with electrospray ionization tandem mass spectrometry and estimation of measurement uncertainty.J AOAC Int2007 Mar-Apr17474525
Safe apples for baby-food production: survey of pesticide treatment regimesleaving minimum residues.Food Addit Contam2007 Jun17487602
Application of liquid chromatography with electrospray tandem mass spectrometryto the determination of a new generation of pesticides in processed fruits andvegetables.J Chromatogr A2004 May 2115146917