Record Information
Version1.0
Creation Date2009-06-23 18:10:09 UTC
Update Date2026-04-06 04:04:15 UTC
Accession NumberCHEM001598
Identification
Common NameTau-fluvalinate
ClassSmall Molecule
DescriptionTau-fluvalinate is a pyrethroid insecticide. A pyrethroid is a synthetic chemical compound similar to the natural chemical pyrethrins produced by the flowers of pyrethrums (Chrysanthemum cinerariaefolium and C. coccineum). Pyrethroids are common in commercial products such as household insecticides and insect repellents. In the concentrations used in such products, they are generally harmless to human beings but can harm sensitive individuals. They are usually broken apart by sunlight and the atmosphere in one or two days, and do not significantly affect groundwater quality except for being toxic to fish. Insects with certain mutations in their sodium channel gene may be resistant to pyrethroid insecticides. (3, 2)
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Ester
  • Ether
  • Household Toxin
  • Nitrile
  • Organic Compound
  • Organochloride
  • Organofluoride
  • Pesticide
  • Pyrethroid
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(RS)-alpha-Cyano-3-phenoxybenzyl N-(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyl)-D-valinateChEBI
N-[2-Chloro-4-(trifluoromethyl)phenyl]-D-valine cyano(3-phenoxyphenyl)methyl esterChEBI
(RS)-a-Cyano-3-phenoxybenzyl N-(2-chloro-a,a,a-trifluoro-p-tolyl)-D-valinateGenerator
(RS)-a-Cyano-3-phenoxybenzyl N-(2-chloro-a,a,a-trifluoro-p-tolyl)-D-valinic acidGenerator
(RS)-alpha-Cyano-3-phenoxybenzyl N-(2-chloro-alpha,alpha,alpha-trifluoro-p-tolyl)-D-valinic acidGenerator
(RS)-Α-cyano-3-phenoxybenzyl N-(2-chloro-α,α,α-trifluoro-p-tolyl)-D-valinateGenerator
(RS)-Α-cyano-3-phenoxybenzyl N-(2-chloro-α,α,α-trifluoro-p-tolyl)-D-valinic acidGenerator
Tau-fluvalinic acidGenerator
MavrikMeSH
FluvalinateMeSH
alpha-Cyano-3-phenoxybenzyl 2-(2-chloro-4-trifluoromethylanilino)-3-methylbutanoateMeSH
Chemical FormulaC26H22ClF3N2O3
Average Molecular Mass502.913 g/mol
Monoisotopic Mass502.127 g/mol
CAS Registry Number102851-06-9
IUPAC Namecyano(3-phenoxyphenyl)methyl (2R)-2-{[2-chloro-4-(trifluoromethyl)phenyl]amino}-3-methylbutanoate
Traditional Nametau-fluvalinate
SMILESCC(C)[C@@H](NC1=CC=C(C=C1Cl)C(F)(F)F)C(=O)OC(C#N)C1=CC=CC(OC2=CC=CC=C2)=C1
InChI IdentifierInChI=1S/C26H22ClF3N2O3/c1-16(2)24(32-22-12-11-18(14-21(22)27)26(28,29)30)25(33)35-23(15-31)17-7-6-10-20(13-17)34-19-8-4-3-5-9-19/h3-14,16,23-24,32H,1-2H3/t23?,24-/m1/s1
InChI KeyINISTDXBRIBGOC-XMMISQBUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Diphenylether
  • Valine or derivatives
  • Diaryl ether
  • Alpha-amino acid or derivatives
  • Benzyloxycarbonyl
  • Trifluoromethylbenzene
  • Phenoxy compound
  • Phenol ether
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Secondary aliphatic/aromatic amine
  • Fatty acid ester
  • Halobenzene
  • Chlorobenzene
  • Fatty acyl
  • Aryl halide
  • Aryl chloride
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary amine
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Alkyl halide
  • Carbonyl group
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceAmber viscous liquid (6).
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00049 g/LALOGPS
logP6.65ALOGPS
logP6.98ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)10.62ChemAxon
pKa (Strongest Basic)0.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.35 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity127.04 m³·mol⁻¹ChemAxon
Polarizability47.41 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0050490000-e2ee8e12709026b89b68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-2190410000-44a165415c49ebf3226cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-3590000000-14c310660632df801c81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-0060190000-3bb7775b7504cf1c161dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-3390230000-66196c3e1fc5249a1794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9630000000-1d1ef52307e32002ce38Spectrum
Toxicity Profile
Route of ExposureInhalation (4) ; oral (4) ; dermal (4) ; eye contact (4).
Mechanism of ToxicityPyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. (7, 4)
MetabolismThe major metabolic pathways are cleavage of ester linkage and oxidation at the acid and alcohol moieties. Ester hydrolysis leads to formation of anilino acid. The anilino acid is further conjugated with amino acids (glycine, serine, threonine, and valine), bile acids (cholic, taurochoric, and taurochenodeoxycholic), and glycerols (oleoyl- and linoleoylglycerol). In addition, an amide derivative of anilino acid was found. These conjugation reactions of anilino acid with bile acid (cholic acid, taurocholic acid, and taurochenodeoxycholic acid) and with glycerol and monoglycerides have rarely been reported as conjugates with xenobiotics. The major urinary metabolites are anilino acid, its hydroxymethyl derivative, its glycine conjugate, haloaniline, and sulfate conjugate of hydroxyhaloaniline. On the other hand, the major fecal metabolites are anilino acid, its amide derivative, and several conjugates of anilino acid with several endogenous components. An unexpected difference between fluvalinate and other pyrethroids is the minimal amount of hydroxylation at the 4'-position of the alcohol moiety. (9)
Toxicity ValuesLD50: 282 mg/kg (Oral, Rat) (6) LD50: >2000 mg/kg (Dermal, Rat) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPyrethroids are used as insecticides. (4)
Minimum Risk LevelNot Available
Health EffectsAt high doses, signs of poisoning attributable to tau-fluvalinate include profuse salivation and pulmonary edema, clonic seizures, opisthotonos (i.e., the spine is bent forward such that a supine body rests on its head and heels), coma, and death. At lower doses, commonly observed effects include paresthesia and erythema. (5)
SymptomsFollowing dermal exposure to tau-flavulinate, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Dizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can result from inhalation or ingestion of large amounts of tau-fluvalinate. Paralysis can occur after exposure. (4)
TreatmentFollowing oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (8)
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 LinkFluvalinate
Chemspider IDNot Available
ChEBI ID39367
PubChem Compound IDNot Available
Kegg Compound IDC18790
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available