Tebuconazole

Basic Info

Common NameTebuconazole(F05978)
2D Structure
FRCD IDF05978
CAS Number107534-96-3
PubChem CID86102
FormulaC16H22ClN3O
IUPAC Name

1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-ylmethyl)pentan-3-ol

InChI Key

PXMNMQRDXWABCY-UHFFFAOYSA-N

InChI

InChI=1S/C16H22ClN3O/c1-15(2,3)16(21,10-20-12-18-11-19-20)9-8-13-4-6-14(17)7-5-13/h4-7,11-12,21H,8-10H2,1-3H3

Canonical SMILES

CC(C)(C)C(CCC1=CC=C(C=C1)Cl)(CN2C=NC=N2)O

Isomeric SMILES

CC(C)(C)C(CCC1=CC=C(C=C1)Cl)(CN2C=NC=N2)O

Synonyms
        
            Elite
        
            Tebuconazole
        
            107534-96-3
        
            Folicur
        
            Fenetrazole
        
            Ethyltrianol
        
            Terbuconazole
        
            Terbutrazole
        
            Etiltrianol
        
            Raxil
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenylbutylamines
Intermediate Tree NodesNot available
Direct ParentPhenylbutylamines
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPhenylbutylamine - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Azole - Heteroaromatic compound - 1,2,4-triazole - Tertiary alcohol - Azacycle - Organoheterocyclic compound - Organonitrogen compound - Organochloride - Organohalogen compound - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Properties

Property NameProperty Value
Molecular Weight307.822
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count6
Complexity326
Monoisotopic Mass307.145
Exact Mass307.145
XLogP3.7
Formal Charge0
Heavy Atom Count21
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+0.8173
Human Intestinal AbsorptionHIA+0.9973
Caco-2 PermeabilityCaco2+0.5202
P-glycoprotein SubstrateSubstrate0.6177
P-glycoprotein InhibitorNon-inhibitor0.7680
Non-inhibitor0.5436
Renal Organic Cation TransporterNon-inhibitor0.6115
Distribution
Subcellular localizationMitochondria0.7070
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7692
CYP450 2D6 SubstrateNon-substrate0.8109
CYP450 3A4 SubstrateSubstrate0.6522
CYP450 1A2 InhibitorNon-inhibitor0.7491
CYP450 2C9 InhibitorNon-inhibitor0.7710
CYP450 2D6 InhibitorNon-inhibitor0.8064
CYP450 2C19 InhibitorNon-inhibitor0.6241
CYP450 3A4 InhibitorInhibitor0.7961
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7845
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7980
Non-inhibitor0.5495
AMES ToxicityNon AMES toxic0.6453
CarcinogensNon-carcinogens0.7205
Fish ToxicityHigh FHMT0.9681
Tetrahymena Pyriformis ToxicityHigh TPT0.9831
Honey Bee ToxicityLow HBT0.8488
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.8051
Carcinogenicity (Three-class)Non-required0.5010
Model Value Unit
Absorption
Aqueous solubility-2.8558LogS
Caco-2 Permeability1.0589LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9943LD50, mol/kg
Fish Toxicity1.3547pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5754pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Soya BeanBritain0.1mg/kg
LeeksBritain0. 4mg/kg
Head CabbageBritain0. 8mg/kg
Brussels SproutsBritain0. 3mg/kg
CauliflowerBritain0.1mg/kg
BroccoliBritain0.1mg/kg
CarrotsBritain0. 4mg/kg
Other Cane Fruit (Other Than Wild)Britain1mg/kg
RaspberriesBritain1mg/kg
BlackberriesBritain1mg/kg
QuincesBritain0.02mg/kg
PearsBritain0.02mg/kg
ApplesBritain0.02mg/kg
WalnutsBritain0.02mg/kg
ChestnutsBritain0.02mg/kg
RyeJapan0.2ppm
BarleyJapan0.05ppm
WheatJapan0.5ppm
Rice(Brown Rice)Japan0.05ppm
RaisinJapan３ppm

References

TitleJournalDatePubmed ID
Does resveratrol retain its antioxidative properties in wine? Redox behaviour of resveratrol in the presence of Cu(II) and tebuconazole.Food Chem2018 Oct 129751913
The evil within? Systemic fungicide application in trees enhances litter quality for an aquatic decomposer-detritivore system.Environ Pollut2018 Oct29883956
Application of Fungicides and Microalgal Phenolic Extracts for the Direct Control of Fumonisin Contamination in Maize.J Agric Food Chem2018 May 1629701989
Unexpected Effects of Propiconazole, Tebuconazole, and Their Mixture on the Receptors CAR and PXR in Human Liver Cells.Toxicol Sci2018 May 129420809
Uptake kinetics of pesticides chlorpyrifos and tebuconazole in the earthworm Eisenia andrei in two different soils.Environ Pollut2018 May29414347
Lab to Field Assessment of the Ecotoxicological Impact of Chlorpyrifos,Isoproturon, or Tebuconazole on the Diversity and Composition of the SoilBacterial Community.Front Microbiol2018 Jun 2930008705
Pesticide load dynamics during stormwater flow events in Mediterranean coastalstreams: Alexander stream case study.Sci Total Environ2018 Jun 129289002
Concentration/time-dependent dissipation, partitioning and plant accumulation of hazardous current-used pesticides and 2-hydroxyatrazine in sand and soil.Chemosphere2018 Jul29621678
Comparison of a new air-assisted sprayer and two conventional sprayers in termsof deposition, loss to the soil and residue of azoxystrobin and tebuconazoleapplied to sunlit greenhouse tomato and field cucumber.Pest Manag Sci2018 Feb28898566
Species composition, toxigenic potential and aggressiveness of Fusarium isolates causing Head Blight of barley in Uruguay.Food Microbiol2018 Dec30166170
The Fungicidal Activity of Tebuconazole Enantiomers against Fusarium graminearum and Its Selective Effect on DON Production under Different Conditions.J Agric Food Chem2018 Apr 1129562133
The Potential of Graphene as an Adsorbent for Five Pesticides from DifferentClasses in Rape Oil Samples Using Dispersive Solid-Phase Extraction.J Anal Methods Chem2018 Apr 129805833
Development and validation of an SPME-GC method for a degradation kinetics study of propiconazole I, propiconazole II and tebuconazole in blueberries inConcordia, the main production area of Argentina.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017May28278123
Gas chromatography-tandem mass spectrometry multi-residual analysis ofcontaminants in Italian honey samples.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017May28277179
Dissipation kinetics and safety evaluation of tebuconazole and trifloxystrobin intea under tropical field conditions.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017Dec28871897
Ambient mass spectrometry: Direct analysis of dimethoate, tebuconazole, andtrifloxystrobin on olive and vine leaves by desorption electrospray ionizationinterface.J Mass Spectrom2017 Nov28762560
Evaluation of Matrix Effects in Multiresidue Analysis of Pesticide Residues inVegetables and Spices by LC-MS/MS.J AOAC Int2017 May 128300025
Determination of eight pesticides in Lycium barbarum by LC-MS/MS and dietary riskassessment.Food Chem2017 Mar 127719897
Tebuconazole and Azoxystrobin Residue Behaviors and Distribution in Field andCooked Peanut.J Agric Food Chem2017 Jun 728499340
Assessment of azole fungicides as a tool to control growth of Aspergillus flavus and aflatoxin B<sub>1</sub> and B<sub>2</sub> production in maize.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017 Jun28349747