Record Information
Version1.0
Creation Date2009-06-23 18:10:09 UTC
Update Date2026-03-26 20:13:30 UTC
Accession NumberCHEM001596
Identification
Common NameFlucythrinate
ClassSmall Molecule
DescriptionFlucythrinate is a synthetic pyrethroid used to control insect pests in apples, cabbage, field corn, head lettuce, and pears, and to control Heliothis spp. in cotton, which is its primary use. It is available in emulsifiable concentrate, water-dispersible granules and wettable powder formulations. The AASTAR product also contains phorate, and it may also be found in formulation with chlorpyrifos, dimethoate, methomyl, or phenthoate. 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, 6)
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Household Toxin
  • Nitrile
  • Organic Compound
  • Organofluoride
  • Pesticide
  • Pyrethroid
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
Flucythrinic acidGenerator
Chemical FormulaC26H23F2NO4
Average Molecular Mass451.462 g/mol
Monoisotopic Mass451.160 g/mol
CAS Registry Number70124-77-5
IUPAC Namecyano(3-phenoxyphenyl)methyl 2-[4-(difluoromethoxy)phenyl]-3-methylbutanoate
Traditional Namepay off
SMILESCC(C)C(C(=O)OC(C#N)C1=CC=CC(OC2=CC=CC=C2)=C1)C1=CC=C(OC(F)F)C=C1
InChI IdentifierInChI=1S/C26H23F2NO4/c1-17(2)24(18-11-13-21(14-12-18)32-26(27)28)25(30)33-23(16-29)19-7-6-10-22(15-19)31-20-8-4-3-5-9-20/h3-15,17,23-24,26H,1-2H3
InChI KeyGBIHOLCMZGAKNG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentPyrethroids
Alternative Parents
Substituents
  • Pyrethroid skeleton
  • Diphenylether
  • Diaryl ether
  • Benzyloxycarbonyl
  • Phenylpropane
  • Phenoxy compound
  • Phenol ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Alkyl fluoride
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alkyl halide
  • 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
AppearanceDark amber, viscous liquid with a faint odor (6).
Experimental Properties
PropertyValue
Melting Point< 25°C
Boiling Point108°C
Solubility6e-05 mg/mL at 25°C [WAUCHOPE,RD et al. (1991A)]
Predicted Properties
PropertyValueSource
Water Solubility0.00079 g/LALOGPS
logP5.98ALOGPS
logP6.77ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)10.62ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area68.55 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.99 m³·mol⁻¹ChemAxon
Polarizability43.78 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4980000000-bdf4d5bb4d2c9a22591cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0131900000-2f3367199c8cc27d3695Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3592500000-640d9745512440e837a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1930000000-440fcfe26b4e4d3502bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0010900000-5538dd40fb3d86d39649Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-2231900000-81a2cd496ce6be0bbd71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9340000000-66de3e0bac0d723b20c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pdj-0690500000-206e855fce5b6d484d8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6s-3890000000-f7b1b9470c37cdaaa982Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1960000000-94ac934883d5460e486dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uml-0491500000-1f1e52c6d0a152e81a11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4m-1791200000-c7d4143d864123f74284Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-4951000000-e0854f1e151d020e0e19Spectrum
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. (8, 4)
MetabolismPrincipal metabolic pathways involved ester cleavage and oxidation at the para position of the alcohol moiety and at the gem-dimethyl groups of the acid moiety. The metabolite with the hydroxyl substitutent in the alcohol moiety was excreted as the sulphate conjugate in urine. A glycine conjugate was also formed. Alcohol radiolabelled flucythrinate yielded at least 29 urinary metabolites, the principal one being 3-(phenoxy)-hippuric acid. With the acid radiolabel the major urinary metabolite was 2-[4-(difluoromethoxy) phenyl]-3-methylbutyric acid, accounting for 60% of urinary radio activity. (7)
Toxicity ValuesLD50: >5000 mg/kg (Dermal, Rabbit) (6) LD50: 81 mg/kg (Oral, Rat) (6) LC50: 4.85 mg/L over 4 hours (Inhalation, 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 flucythrinate 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)
Symptoms Following dermal exposure to flucythrinate, 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 flucythrinate. 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. (9)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0252327
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFlucythrinate
Chemspider ID46213
ChEBI IDNot Available
PubChem Compound ID50980
Kegg Compound IDC14524
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available