Fluazinam (CHEM002803)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (30)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:51 UTC
Update Date2016-11-09 01:08:58 UTC
Accession NumberCHEM002803
Identification
Common NameFluazinam
ClassSmall Molecule
DescriptionFluazinam is a broad-spectrum fungicide used in agriculture. It is classed as a diarylamine and more specifically an arylaminopyridine. The mode of action involves the compound being an extremely potent uncoupler of oxidative phosphorylation in mitochondria and also having high reactivity with thiols. It is unique amongst uncouplers in displaying broad-spectrum activity against fungi and also very low toxicity to mammals due to it being rapidly metabolised to a compound without uncoupling activity. Fluazinam is a protectant fungicide, but is neither systemic or curative. It acts by inhibiting the germination of spores and the development of infection structures. Although it has activity against many fungi, it is less potent against rusts and powdery mildew and as such has not been commercialised for use in cereal crops. It is widely used to control late blight (P. infestans) in potato due to its activity against the zoospores of the pathogen which makes it particularly effective at controlling infection of the potato tubers.
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Fungicide
  • Organic Compound
  • Organochloride
  • Organofluoride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-alpha,alpha,alpha-trifluoro-2,6-dinitro-p-toluidineChEBI
ShirlanChEBI
3-Chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-a,a,a-trifluoro-2,6-dinitro-p-toluidineGenerator
3-Chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-α,α,α-trifluoro-2,6-dinitro-p-toluidineGenerator
3-chloro-N-(3-chloro-2,6-dinitro-4-Trifluoromethylphenyl)-5-trifluoromethyl-2-pyridinamineMeSH
Chemical FormulaC13H4Cl2F6N4O4
Average Molecular Mass465.092 g/mol
Monoisotopic Mass463.951 g/mol
CAS Registry Number79622-59-6
IUPAC Name3-chloro-N-[3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl]-5-(trifluoromethyl)pyridin-2-amine
Traditional Namefluazinam
SMILES[O-][N+](=O)C1=CC(=C(Cl)C(=C1NC1=C(Cl)C=C(C=N1)C(F)(F)F)[N+]([O-])=O)C(F)(F)F
InChI IdentifierInChI=1S/C13H4Cl2F6N4O4/c14-6-1-4(12(16,17)18)3-22-11(6)23-9-7(24(26)27)2-5(13(19,20)21)8(15)10(9)25(28)29/h1-3H,(H,22,23)
InChI KeyUZCGKGPEKUCDTF-UHFFFAOYSA-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
  • Nitrobenzene
  • Nitroaromatic compound
  • Aniline or substituted anilines
  • Aminopyridine
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Imidolactam
  • Heteroaromatic compound
  • C-nitro compound
  • Organic nitro compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organoheterocyclic compound
  • Secondary amine
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organic oxoazanium
  • Organic zwitterion
  • Organochloride
  • Organofluoride
  • Organohalogen compound
  • Organonitrogen compound
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Alkyl halide
  • 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
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 Solubility6.7e-05 g/LALOGPS
logP3.99ALOGPS
logP6.93ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)2.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area116.56 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity88.91 m³·mol⁻¹ChemAxon
Polarizability32.19 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-76ecafa111b00290dc24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0000900000-5e049539938436da1febSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01xw-2400900000-7b38ad9efd4cea0f3179Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-49b02640119a09eff3bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-ea96eb23e48234da362cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06xx-1103900000-29708c9ff9b2f6f3125cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureInhalation and dermal contact.
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 EffectsFluazinam increases the risks of thyroid gland follicular cell and hepatocellular tumors in rats and mice. According to The Cancer Assessment Review Committee (CARC), there is suggestive evidence of carcinogenicity, but not sufficient to assess human carcinogenic potential.
SymptomsFluazinam can cause eye irritation and moderate skin sensitization.
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 LinkFluazinam
Chemspider IDNot Available
ChEBI ID81843
PubChem Compound ID91731
Kegg Compound IDC18578
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19837458
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21907236
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22465686
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23464902
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24427089
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24813983
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=7774188