Flusilazole (CHEM002811)

Record Information
Version1.0
Creation Date2013-04-25 07:56:51 UTC
Update Date2026-08-19 15:07:24 UTC
Accession NumberCHEM002811
Identification
Common NameFlusilazole
ClassSmall Molecule
Description
Flusilazole (DPX-H6573) is an organosilicon fungicide invented by DuPont, which is used to control fungal infections on a variety of fruit and vegetable crops. It is moderately toxic to animals and has been shown to produce birth defects and embryotoxicity at high doses.
Contaminant Sources
  • FooDB Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Food Toxin
  • Fungicide
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Pesticide
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-[[Bis(4-fluorophenyl)methylsilyl]methyl]-1H-1,2,4-triazoleChEBI
Bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-ylmethyl)silaneChEBI
Di(4-fluorophenyl)(1,2,4-triazole-2-ylmethyl)methylsilaneChEBI
DPX-H 6573ChEBI
FlusilazolChEBI
NustarChEBI
1-[[Bis(4-fluorophenyl)methylsilyl]methyl]-1H-1,2,4-triazole, 9ciHMDB
Bis(4-fluorophenyl)methyl(1H-1,2,4-triazol-1-ylmethyl)silaneHMDB
DPD 78710FHMDB
DPX-N6573HMDB
FluzilazolHMDB
OlympHMDB
PPX-H6573HMDB
PunchHMDB
Punch (pesticide)HMDB
Punch 40EcHMDB
SanctionHMDB
DPX-H6573MeSH
Chemical FormulaC16H15F2N3Si
Average Molecular Mass315.393 g/mol
Monoisotopic Mass315.100 g/mol
CAS Registry Number85509-19-9
IUPAC Name1-{[bis(4-fluorophenyl)(methyl)silyl]methyl}-1H-1,2,4-triazole
Traditional Nameflusilazole
SMILESC[Si](CN1C=NC=N1)(C1=CC=C(F)C=C1)C1=CC=C(F)C=C1
InChI IdentifierInChI=1S/C16H15F2N3Si/c1-22(12-21-11-19-10-20-21,15-6-2-13(17)3-7-15)16-8-4-14(18)5-9-16/h2-11H,12H2,1H3
InChI KeyFQKUGOMFVDPBIZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fluorobenzenes. Fluorobenzenes are compounds containing one or more fluorine atoms attached to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentFluorobenzenes
Alternative Parents
Substituents
  • Fluorobenzene
  • Alkylarylsilane
  • Aryl fluoride
  • Aryl halide
  • Azole
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Azacycle
  • Organic metalloid salt
  • Organoheterocyclic compound
  • Alkylsilane
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organosilicon compound
  • Organic salt
  • 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 Point48°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0043 g/LALOGPS
logP3.55ALOGPS
logP4.68ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)2.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.71 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.79 m³·mol⁻¹ChemAxon
Polarizability29.4 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityFlusilazole has a dose-related inhibition of serum testosterone and estradiol concentrations in rats. This inhibition of testosterone and estradiol biosynthesis may disrupt the hypothalamus–pituitary–testis axis, resulting in overstimulation of the testicular endocrine tissues and increase the risk of Leydig-cell tumours.
MetabolismNot Available
Toxicity ValuesLD50 (rat, oral) =1110 mg/kg (m) LD50 (rat, dermal) >2000 mg/kg
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 EffectsFlusilazole can cause testicular Leydig-cell tumours and bladder tumours in rats and hepatocellular tumours in mouse. An increased gestation length and increased placental weight have been found in the reproductive toxicity studies.
SymptomsSymptoms include weight loss, weakness, lethargy, alopecia and diarrhoea. At higher dose, prostration, salivation, laboured breathing, convulsions, and loss of righting reflex would be expected. Flusilazole can also cause mild erythema at the site of application.
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0039815
FooDB IDFDB019466
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFlusilazole
Chemspider ID66326
ChEBI ID81922
PubChem Compound ID73675
Kegg Compound IDC18733
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17187383
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21238576
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21290102
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22382673
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23657738
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25149233
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12. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.