Triflumizole (CHEM003507)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (35)XML
Record Information
Version1.0
Creation Date2014-08-29 06:51:46 UTC
Update Date2016-11-09 01:09:09 UTC
Accession NumberCHEM003507
Identification
Common NameTriflumizole
ClassSmall Molecule
DescriptionTriflumizole is a conazole fungicide used to control powdery mildew, scab and other diseases on top fruit, grapes and other crops. Its mode of action is systemic with protective and curative action. It is an inhibitor of chitin biosynthesis.
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ether
  • Fungicide
  • Organic Compound
  • Organochloride
  • Organofluoride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1E)-N-[4-Chloro-2-(trifluoromethyl)phenyl]-1-(1H-imidazol-1-yl)-2-propoxyethan-1-imineChEBI
(e)-4-Chloro-alpha,alpha,alpha-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-O-toluidineChEBI
1-[(1E)-1-[[4-Chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazoleChEBI
[N(e)]-4-Chloro-N-[1-(1H-imidazol-1-yl)-2-propoxyethylidene]-2-(trifluoromethyl)benzenamineChEBI
CondorChEBI
NF-114ChEBI
ProcureChEBI
TerraguardChEBI
TriflumizolChEBI
TrifumineChEBI
(e)-4-Chloro-a,a,a-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-O-toluidineGenerator
(e)-4-Chloro-α,α,α-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-O-toluidineGenerator
Chemical FormulaC15H15ClF3N3O
Average Molecular Mass345.747 g/mol
Monoisotopic Mass345.086 g/mol
CAS Registry Number68694-11-1 and 99387-89-0
IUPAC Name(1E)-N-[4-chloro-2-(trifluoromethyl)phenyl]-1-(1H-imidazol-1-yl)-2-propoxyethan-1-imine
Traditional Name(1E)-N-[4-chloro-2-(trifluoromethyl)phenyl]-1-(imidazol-1-yl)-2-propoxyethanimine
SMILESCCCOC\C(=N/C1=C(C=C(Cl)C=C1)C(F)(F)F)N1C=CN=C1
InChI IdentifierInChI=1S/C15H15ClF3N3O/c1-2-7-23-9-14(22-6-5-20-10-22)21-13-4-3-11(16)8-12(13)15(17,18)19/h3-6,8,10H,2,7,9H2,1H3/b21-14+
InChI KeyHSMVPDGQOIQYSR-KGENOOAVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassTrifluoromethylbenzenes
Direct ParentTrifluoromethylbenzenes
Alternative Parents
Substituents
  • Trifluoromethylbenzene
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Abc transportersNot Availablemap02010
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 Solubility0.0036 g/LALOGPS
logP3.55ALOGPS
logP3.58ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)6.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.41 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.83 m³·mol⁻¹ChemAxon
Polarizability31.91 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-2009000000-223619f04a5375ff535fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-9001000000-83279ba9ad64f257b497Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-cad3b2a3f1872a3d66daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9004000000-15490996bab589c6f985Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9113000000-fbc0f366bc0562a59caeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9441000000-c0009cc1d235a4aebeb2Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsIn human, a neuromuscular impairment and decreased locomotor activity were observed following a single exposure of 100 mg/kg/day. The liver is the primary target organ of triflumizole in the rat, mouse, and dog. It increased liver weight, hepatocyte fatty vacuolization, hypertrophy, inflammation, fatty degeneration, and caused necrosis. Chronic effects of triflumizole included hepatocyte fatty vacuolization, hepatocyte hypertrophy, focal inflammation, and necrosi,; fatty degeneration, eosinophilic foci of hepatocyte alteration, hepatic nodules, bile duct hyperplasia, and hyaline degeneration/fibrosis of the bile duct. Liver effects were seen in rat and mouse subchronic and chronic/carcinogenicity studies. The fetal effects were also seen in rats. Triflumizole has a reproductive toxicity as well, the gestation length was increased in rats receiving high dose of triflumizole.
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 ID81784
PubChem Compound IDNot Available
Kegg Compound IDC18493
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17723736
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21589122
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23086663
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23211365
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3624378
6.