Basic Info

Common NameMetconazole(F06036)
2D Structure
FRCD IDF06036
CAS Number125116-23-6
PubChem CID86210
FormulaC17H22ClN3O
IUPAC Name

5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol

InChI Key

XWPZUHJBOLQNMN-UHFFFAOYSA-N

InChI

InChI=1S/C17H22ClN3O/c1-16(2)8-7-14(9-13-3-5-15(18)6-4-13)17(16,22)10-21-12-19-11-20-21/h3-6,11-12,14,22H,7-10H2,1-2H3

Canonical SMILES

CC1(CCC(C1(CN2C=NC=N2)O)CC3=CC=C(C=C3)Cl)C

Isomeric SMILES

CC1(CCC(C1(CN2C=NC=N2)O)CC3=CC=C(C=C3)Cl)C

Synonyms
        
            XWPZUHJBOLQNMN-UHFFFAOYSA-N
        
            Cyclopentanol, 5-(4-chlorophenyl)methyl-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-
        
            Metconazole
        
            125116-23-6
        
            CHEBI:81773
        
            5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol
        
            Metconazole [ISO]
        
            AC1L3B3T
        
            DSSTox_CID_14497
        
            DSSTox_RID_79159
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassMonoterpenoids
Intermediate Tree NodesNot available
Direct ParentIridoids and derivatives
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsAromatic monoterpenoid - 11-noriridane monoterpenoid - Monocyclic monoterpenoid - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Cyclopentanol - Benzenoid - 1,2,4-triazole - Tertiary alcohol - Azole - Cyclic alcohol - Heteroaromatic compound - Azacycle - Organoheterocyclic compound - Hydrocarbon derivative - Organopnictogen compound - Alcohol - Organic oxygen compound - Organic nitrogen compound - Organohalogen compound - Organochloride - Organonitrogen compound - Organooxygen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Properties

Property NameProperty Value
Molecular Weight319.833
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Complexity384
Monoisotopic Mass319.145
Exact Mass319.145
XLogP3.7
Formal Charge0
Heavy Atom Count22
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+0.5548
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.5000
P-glycoprotein SubstrateSubstrate0.6645
P-glycoprotein InhibitorNon-inhibitor0.6587
Inhibitor0.6172
Renal Organic Cation TransporterNon-inhibitor0.5567
Distribution
Subcellular localizationMitochondria0.6735
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7448
CYP450 2D6 SubstrateNon-substrate0.7925
CYP450 3A4 SubstrateSubstrate0.6938
CYP450 1A2 InhibitorNon-inhibitor0.7905
CYP450 2C9 InhibitorNon-inhibitor0.7137
CYP450 2D6 InhibitorNon-inhibitor0.8085
CYP450 2C19 InhibitorNon-inhibitor0.5328
CYP450 3A4 InhibitorInhibitor0.7743
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7542
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.6992
Non-inhibitor0.6834
AMES ToxicityNon AMES toxic0.6787
CarcinogensNon-carcinogens0.8165
Fish ToxicityHigh FHMT0.9966
Tetrahymena Pyriformis ToxicityHigh TPT0.9703
Honey Bee ToxicityLow HBT0.8506
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7426
Carcinogenicity (Three-class)Non-required0.5605

Model Value Unit
Absorption
Aqueous solubility-2.9806LogS
Caco-2 Permeability0.9035LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2713LD50, mol/kg
Fish Toxicity1.3391pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6384pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Fat1011020European Union0.02*24/11/2016
(b) bovine (American buffalo, Banteng, Buffalo, European buffalo/wisent, Gayal, Yak (domestic), Zebu, Hybrids of genera Bison, Bos, Bubalus and Poëphagus,)1012000European Union0.02*24/11/2016
(c) sheep (Mouflon (farmed),)1013000European Union0.02*24/11/2016
Edible offals (other than liver and kidney)1013050European Union0.02*24/11/2016
(f) poultry (Bobwhite quail, Chicken (including silkie chicken), Collared Dove, Duck, Geese, Green peafowl, Guinea fowl, Japanese quail, Muskovy duck, Mute swan, Partridge, Peafowl, Pheasant, Pigeo...1016000European Union0.02*24/11/2016
Macadamias0120070European Union0.05*24/11/2016
Liver1011030European Union0.02*24/11/2016
Kidney1011040European Union0.02*24/11/2016
Edible offals (other than liver and kidney)1011050European Union0.02*24/11/2016
Others (2)1011990European Union0.02*24/11/2016
Muscle1012010European Union0.02*24/11/2016
Fat1012020European Union0.02*24/11/2016
Liver1012030European Union0.02*24/11/2016
Kidney1012040European Union0.02*24/11/2016
Muscle1013010European Union0.02*24/11/2016
Fat1013020European Union0.02*24/11/2016
Liver1013030European Union0.02*24/11/2016
Kidney1013040European Union0.02*24/11/2016
Others (2)1013990European Union0.02*24/11/2016
d) goat1014000European Union0.02*24/11/2016

References

TitleJournalDatePubmed ID
Species composition, toxigenic potential and aggressiveness of Fusarium isolates causing Head Blight of barley in Uruguay.Food Microbiol2018 Dec30166170
Evaluations of Insecticides and Fungicides for Reducing Attack Rates of a newinvasive ambrosia beetle (Euwallacea Sp., Coleoptera: Curculionidae: Scolytinae) in Infested Landscape Trees in California.J Econ Entomol2017 Aug 128854652
Sensitive determination of mixtures of neonicotinoid and fungicide residues inpollen and single bumblebees using a scaled down QuEChERS method for exposureassessment.Anal Bioanal Chem2015 Oct26329280
Corn silage from corn treated with foliar fungicide and performance of Holstein cows.J Dairy Sci2015 Dec26476949
Bioaccumulation and biotransformation of chiral triazole fungicides in rainbow trout (Oncorhynchus mykiss).Aquat Toxicol2006 Dec 3017118468
Quantification of trichothecene-producing Fusarium species in harvested grain by competitive PCR to determine efficacies of fungicides against Fusarium head blight of winter wheat.Appl Environ Microbiol2001 Apr11282607