Fenbuconazole (CHEM003466)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (16)XML
Record Information
Version1.0
Creation Date2014-08-29 06:51:43 UTC
Update Date2016-11-09 01:09:09 UTC
Accession NumberCHEM003466
Identification
Common NameFenbuconazole
ClassSmall Molecule
DescriptionFenbuconazole is a triazole fungicide intended for use as an agricultural and horticultural fungicide spray for the control of leaf spot, yellow and brown rust, powdery mildew and net blotch on wheat and barley and apple scab, pear scab and apple powdery mildew on apples and pears. It is a systemic protectant and curative which acts by inhibiting sterol biosynthesis in fungi. Fenbuconazole is rapidly absorbed and eliminated, mainly in the faeces through significant biliary excretion; there was no evidence of significant retention in tissues. Fenbuconazole was of low acute toxicity when administered orally (LD50 > 2000 mg/kg bw), dermally (LD50 > 5000 mg/kg bw), or by inhalation (LC50 > 2.1 mg/litre air). It was not irritating to the skin or eyes.
Contaminant Sources
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Fungicide
  • Nitrile
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
alpha(2-(4-Chlorophenyl)ethyl)-alpha-phenyl-1H-1,2,4-triazole-1-propanentrileMeSH
(RS)-4-(4-Chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butyrontrileMeSH
Chemical FormulaC19H17ClN4
Average Molecular Mass336.818 g/mol
Monoisotopic Mass336.114 g/mol
CAS Registry Number114369-43-6
IUPAC Name4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butanenitrile
Traditional Namefenbuconazole
SMILESClC1=CC=C(CCC(CN2C=NC=N2)(C#N)C2=CC=CC=C2)C=C1
InChI IdentifierInChI=1S/C19H17ClN4/c20-18-8-6-16(7-9-18)10-11-19(12-21,13-24-15-22-14-23-24)17-4-2-1-3-5-17/h1-9,14-15H,10-11,13H2
InChI KeyRQDJADAKIFFEKQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as linear 1,3-diarylpropanoids. These are organic compounds with a structure based on a C6-C3-C6 skeleton, where the two benzene rings are not linked together.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassNot Available
Direct ParentLinear 1,3-diarylpropanoids
Alternative Parents
Substituents
  • Linear 1,3-diarylpropanoid
  • Phenylbutylamine
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Azacycle
  • Organoheterocyclic compound
  • Carbonitrile
  • Nitrile
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organochloride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
  • Microsome
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP3.51ALOGPS
logP4.35ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)2.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area54.5 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity107.17 m³·mol⁻¹ChemAxon
Polarizability35.24 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0029000000-ab2765f740df666abc0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0091000000-1351d89ae0e3a93c71d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0610-4960000000-f9acf8d2393df15438ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-9106000000-258ceea9a032d3f9f7a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9305000000-ce4627268ce1785eed07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-3e1e9bdd38e0805ef44cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityOrganic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (2)
MetabolismOrganic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (1)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID83920
PubChem Compound ID86138
Kegg Compound IDC18461
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available