Basic Info

Common NameTetraconazole(F05143)
2D Structure
Description

Tetraconazole is a liquid fungicide for control of Cercospora leafspot and powdery mildew on sugar beets.

FRCD IDF05143
CAS Number112281-77-3
PubChem CID80277
FormulaC13H11Cl2F4N3O
IUPAC Name

1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1,2,4-triazole

InChI Key

LQDARGUHUSPFNL-UHFFFAOYSA-N

InChI

InChI=1S/C13H11Cl2F4N3O/c14-9-1-2-10(11(15)3-9)8(4-22-7-20-6-21-22)5-23-13(18,19)12(16)17/h1-3,6-8,12H,4-5H2

Canonical SMILES

C1=CC(=C(C=C1Cl)Cl)C(CN2C=NC=N2)COC(C(F)F)(F)F

Isomeric SMILES

C1=CC(=C(C=C1Cl)Cl)C(CN2C=NC=N2)COC(C(F)F)(F)F

Synonyms
        
            1-(2-(2,4-Dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl)-1H-1,2,4-triazole
        
            Tetraconazole
        
            Eminent
        
            112281-77-3
        
            Tetraconazole [ISO]
        
            AG 4454
        
            CHEBI:83999
        
            M 14360
        
            1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1,2,4-triazole
        
            1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1H-1,2,4-triazole
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassHalobenzenes
Intermediate Tree NodesChlorobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
Substituents1,3-dichlorobenzene - Aryl chloride - Aryl halide - Azole - Heteroaromatic compound - 1,2,4-triazole - Dialkyl ether - Ether - Azacycle - Organoheterocyclic compound - Organofluoride - Organochloride - Organohalogen compound - Alkyl halide - Hydrocarbon derivative - Alkyl fluoride - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.

Properties

Property NameProperty Value
Molecular Weight372.145
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Complexity381
Monoisotopic Mass371.022
Exact Mass371.022
XLogP4.4
Formal Charge0
Heavy Atom Count23
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9810
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.6082
P-glycoprotein SubstrateNon-substrate0.7301
P-glycoprotein InhibitorNon-inhibitor0.8648
Non-inhibitor0.7294
Renal Organic Cation TransporterInhibitor0.5745
Distribution
Subcellular localizationMitochondria0.8929
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8433
CYP450 2D6 SubstrateNon-substrate0.8849
CYP450 3A4 SubstrateNon-substrate0.5872
CYP450 1A2 InhibitorInhibitor0.8836
CYP450 2C9 InhibitorInhibitor0.6340
CYP450 2D6 InhibitorNon-inhibitor0.8705
CYP450 2C19 InhibitorInhibitor0.8020
CYP450 3A4 InhibitorNon-inhibitor0.6885
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6432
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7098
Non-inhibitor0.6471
AMES ToxicityNon AMES toxic0.6297
CarcinogensNon-carcinogens0.8092
Fish ToxicityHigh FHMT0.9891
Tetrahymena Pyriformis ToxicityHigh TPT0.9878
Honey Bee ToxicityLow HBT0.8233
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.5952
Carcinogenicity (Three-class)Non-required0.4650

Model Value Unit
Absorption
Aqueous solubility-3.8360LogS
Caco-2 Permeability1.4574LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5785LD50, mol/kg
Fish Toxicity1.2093pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.9660pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
CranberryJapan2ppm
BlueberryJapan2ppm
Beans (with pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, ...0260010European Union0.02*27/01/2013
Citrus fruits0110000European Union0.02*27/01/2013
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.02*27/01/2013
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.02*27/01/2013
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.02*27/01/2013
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.02*27/01/2013
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.02*27/01/2013
Others (2)0110990European Union0.02*27/01/2013
Tree nuts0120000European Union0.02*27/01/2013
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.02*27/01/2013
Brazil nuts0120020European Union0.02*27/01/2013
Cashew nuts0120030European Union0.02*27/01/2013
Chestnuts0120040European Union0.02*27/01/2013
Coconuts (Areca nuts/betel nuts,)0120050European Union0.02*27/01/2013
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.02*27/01/2013
Macadamias0120070European Union0.02*27/01/2013
Pecans (Hickory nuts,)0120080European Union0.02*27/01/2013
Sichuan pepper (Japanese pepper, Uzazi,)0820020European Union0.02*27/01/2013

References

TitleJournalDatePubmed ID
Dissipation behaviour, residue distribution and dietary risk assessment oftetraconazole and kresoxim-methyl in greenhouse strawberry via RRLC-QqQ-MS/MStechnique.Ecotoxicol Environ Saf2018 Feb29195223
Enhanced Dissipation of Triazole and Multiclass Pesticide Residues on Grapesafter Foliar Application of Grapevine-Associated Bacillus Species.J Agric Food Chem2015 Dec 2326492206
Development and application of recombinant antibody-based immunoassays totetraconazole residue analysis in fruit juices.Food Chem2014 Jan 1524054232
Effect of preharvest anti-fungal compounds on Aspergillus steynii and A. carbonarius under fluctuating and extreme environmental conditions.Int J Food Microbiol2012 Oct 122947301
Pesticide residues in Portuguese strawberries grown in 2009-2010 using integratedpest management and organic farming.Environ Sci Pollut Res Int2012 Nov22562348
[Determination of 11 triazole fungicides in fruits using solid phase extractionand gas chromatography-tandem mass spectrometry].Se Pu2012 Mar22715691
Simultaneous multiresidue analysis of 41 pesticide residues in cooked foodstuffusing QuEChERS: Comparison with classical method.Food Chem2011 Sep 125214356
Development of monoclonal immunoassays for the determination of triazolefungicides in fruit juices.J Agric Food Chem2008 Oct 818783243
Synthesis and antifungal activity of a series of N-substituted[2-(2,4-dichlorophenyl)-3-(1,2,4-triazol-1-yl)]propylamines.J Agric Food Chem2007 Oct 317896810
Safe apples for baby-food production: survey of pesticide treatment regimesleaving minimum residues.Food Addit Contam2007 Jun17487602
Determination of tetraconazole and diniconazole fungicide residues in tomatoesand green beans by capillary gas chromatography.Yakugaku Zasshi2007 Jun17541250
Bioaccumulation and biotransformation of chiral triazole fungicides in rainbow trout (Oncorhynchus mykiss).Aquat Toxicol2006 Dec 3017118468
Simultaneous determination of six triazolic pesticide residues in apple and pear pulps by liquid chromatography with ultraviolet diode array detection.J AOAC Int2001 Sep-Oct11601474
Synthesis, fungicidal activity, and QSAR of a series of2-dichlorophenyl-3-triazolylpropyl ethers.J Agric Food Chem2000 Jun10888582
Pesticide residues in grapes, wine, and their processing products.J Agric Food Chem2000 Apr10775335
Pesticides in fermentative processes of wine.J Agric Food Chem1999 Sep10552734

Targets

General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Prostaglandin e receptor activity
Specific Function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the relaxing effect of this receptor on smooth muscle.
Gene Name:
PTGER2
Uniprot ID:
P43116
Molecular Weight:
39759.945 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
Gene Name:
CYP2J2
Uniprot ID:
P51589
Molecular Weight:
57610.165 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular Weight:
55710.075 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Uniprot ID:
P05184
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Transcription regulatory region dna binding
Specific Function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
Gene Name:
AHR
Uniprot ID:
P35869
Molecular Weight:
96146.705 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Monoamine transmembrane transporter activity
Specific Function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular Weight:
68494.255 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]