Epoxiconazole

Basic Info

Common NameEpoxiconazole(F05746)
2D Structure
FRCD IDF05746
CAS Number106325-08-0
PubChem CID3317081
FormulaC17H13ClFN3O
IUPAC Name

1-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]-1,2,4-triazole

InChI Key

ZMYFCFLJBGAQRS-UHFFFAOYSA-N

InChI

InChI=1S/C17H13ClFN3O/c18-15-4-2-1-3-14(15)16-17(23-16,9-22-11-20-10-21-22)12-5-7-13(19)8-6-12/h1-8,10-11,16H,9H2

Canonical SMILES

C1=CC=C(C(=C1)C2C(O2)(CN3C=NC=N3)C4=CC=C(C=C4)F)Cl

Isomeric SMILES

C1=CC=C(C(=C1)C2C(O2)(CN3C=NC=N3)C4=CC=C(C=C4)F)Cl

Synonyms
        
            1-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]-1,2,4-triazole
        
            Epoxiconazole
        
            135319-73-2
        
            CHEBI:83758
        
            133855-98-8
        
            (2RS,3SR)-1-[3-(2-Chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazole
        
            epociconazole
        
            106325-08-0
        
            1H-1,2,4-Triazole, 1-[[(2R,3S)-3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiranyl]methyl]-, rel-
        
            AC1MOA5R
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassStilbenes
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentStilbenes
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsStilbene - Chlorobenzene - Fluorobenzene - Halobenzene - Aryl chloride - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Azole - Heteroaromatic compound - 1,2,4-triazole - Oxacycle - Azacycle - Dialkyl ether - Oxirane - Ether - Organoheterocyclic compound - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Organohalogen compound - Organochloride - Organofluoride - Organonitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Properties

Property NameProperty Value
Molecular Weight329.759
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Complexity421
Monoisotopic Mass329.073
Exact Mass329.073
XLogP3.2
Formal Charge0
Heavy Atom Count23
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9751
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.6174
P-glycoprotein SubstrateNon-substrate0.6755
P-glycoprotein InhibitorNon-inhibitor0.7220
Non-inhibitor0.6845
Renal Organic Cation TransporterNon-inhibitor0.5333
Distribution
Subcellular localizationMitochondria0.8656
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7722
CYP450 2D6 SubstrateNon-substrate0.8693
CYP450 3A4 SubstrateSubstrate0.6071
CYP450 1A2 InhibitorInhibitor0.5901
CYP450 2C9 InhibitorInhibitor0.7369
CYP450 2D6 InhibitorNon-inhibitor0.7567
CYP450 2C19 InhibitorInhibitor0.7866
CYP450 3A4 InhibitorInhibitor0.6324
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.9329
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8705
Non-inhibitor0.5348
AMES ToxicityNon AMES toxic0.6503
CarcinogensNon-carcinogens0.7000
Fish ToxicityHigh FHMT0.9852
Tetrahymena Pyriformis ToxicityHigh TPT0.9704
Honey Bee ToxicityLow HBT0.8772
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.5802
Carcinogenicity (Three-class)Non-required0.4944
Model Value Unit
Absorption
Aqueous solubility-4.1352LogS
Caco-2 Permeability1.5438LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.6177LD50, mol/kg
Fish Toxicity0.9323pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.0172pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Terrestrial Mammals,KidneyJapan0.05ppm
Other Poultry,EggsJapan0.01ppm
Chicken,EggsJapan0.01ppm
Other Poultry Animals,Edible OffalJapan0.02ppm
Chicken,Edible OffalJapan0.02ppm
Other Poultry Animals,KidneyJapan0.02ppm
Chicken,KidneyJapan0.02ppm
Other Poultry Animals,LiverJapan0.02ppm
Chicken,LiverJapan0.02ppm
Other Poultry Animals,FatJapan0.05ppm
Chicken,FatJapan0.05ppm
Other Poultry Animals,MuscleJapan0.02ppm
Chicken,MuscleJapan0.02ppm
MilkJapan0.01ppm
Other Terrestrial Mammals,Edible OffalJapan0.05ppm
Pig,Edible OffalJapan0.05ppm
Cattle,Edible OffalJapan0.05ppm
Pig,KidneyJapan0.05ppm
Cattle,KidneyJapan0.05ppm
Other Terrestrial Mammals,LiverJapan0.05ppm

References

TitleJournalDatePubmed ID
Concentration/time-dependent dissipation, partitioning and plant accumulation of hazardous current-used pesticides and 2-hydroxyatrazine in sand and soil.Chemosphere2018 Jul29621678
Enantioselective bioaccumulation following exposure of adult zebrafish (Danio rerio) to epoxiconazole and its effects on metabolomic profile as well as genes expression.Environ Pollut2017 Oct28601015
Mycotoxin and fungicide residues in wheat grains from fungicide-treated plants measured by a validated LC-MS method.Food Chem2017 Apr 127855933
Human and ecological risk assessment of a crop protection chemical: a case study with the azole fungicide epoxiconazole.Crit Rev Toxicol2014 Feb24274332
Effect of phenylpyrrole-resistance on fitness parameters and ochratoxin production in Aspergillus carbonarius.Int J Food Microbiol2013 Aug 123800740
Effect of preharvest anti-fungal compounds on Aspergillus steynii and A. carbonarius under fluctuating and extreme environmental conditions.Int J Food Microbiol2012 Oct 122947301
Effect of anilinopyrimidine resistance on aflatoxin production and fitness parameters in Aspergillus parasiticus Speare.Int J Food Microbiol2011 Mar 3021411166
Endocrine-disrupting activities in vivo of the fungicides tebuconazole and epoxiconazole.Toxicol Sci2007 Dec17785682
Dissipation of epoxiconazole in the paddy field under subtropical conditions of Taiwan.J Environ Sci Health B2001 Jul11495019