Cyfluthrin (CHEM000889)

Record Information
Version1.0
Creation Date2009-06-18 17:03:35 UTC
Update Date2026-05-14 19:37:44 UTC
Accession NumberCHEM000889
Identification
Common NameCyfluthrin
ClassSmall Molecule
Description
Cyfluthrin is a synthetic (type 2) pyrethroid insecticide that has both contact and stomach poison action. It is a non-systemic chemical used to control cutworms, ants, silverfish, cockroaches, termites, grain beetles, weevils, mosquitoes, fleas, flies, corn earworms, tobacco budworm, codling moth, European corn borer, cabbageworm, loopers, armyworms, boll weevil, alfalfa weevil, Colorado potato beetle, and many others. Its primary agricultural uses have been for control of chewing and sucking insects on crops such as cotton, turf, ornamentals, hops, cereal, corn, deciduous fruit, peanuts, potatoes, and other vegetables. Cyfluthrin is also used in public health situations and for structural pest control. (5)
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Household Toxin
  • Insecticide
  • Nitrile
  • Organic Compound
  • Organochloride
  • Organofluoride
  • Pesticide
  • Pyrethroid
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(R,S)-alpha-Cyano-4-fluoro-3-phenoxybenzyl-(1R,S)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateChEBI
CylenceKegg
(R,S)-a-Cyano-4-fluoro-3-phenoxybenzyl-(1R,S)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
(R,S)-a-Cyano-4-fluoro-3-phenoxybenzyl-(1R,S)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(R,S)-alpha-Cyano-4-fluoro-3-phenoxybenzyl-(1R,S)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
(R,S)-Α-cyano-4-fluoro-3-phenoxybenzyl-(1R,S)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylateGenerator
(R,S)-Α-cyano-4-fluoro-3-phenoxybenzyl-(1R,S)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acidGenerator
beta-CyfluthrinMeSH
cyano(4-fluoro-3-Phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylateMeSH
Chemical FormulaC22H18Cl2FNO3
Average Molecular Mass434.288 g/mol
Monoisotopic Mass433.065 g/mol
CAS Registry Number68359-37-5
IUPAC Namecyano(4-fluoro-3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Traditional Nameβ-cyfluthrin
SMILESCC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=C(F)C(OC2=CC=CC=C2)=C1
InChI IdentifierInChI=1S/C22H18Cl2FNO3/c1-22(2)15(11-19(23)24)20(22)21(27)29-18(12-26)13-8-9-16(25)17(10-13)28-14-6-4-3-5-7-14/h3-11,15,18,20H,1-2H3
InChI KeyQQODLKZGRKWIFG-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
  • Phenoxy compound
  • Phenol ether
  • Fluorobenzene
  • Halobenzene
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Cyclopropanecarboxylic acid or derivatives
  • Benzenoid
  • Carboxylic acid ester
  • Ketene acetal or derivatives
  • Carboxylic acid derivative
  • Chloroalkene
  • Haloalkene
  • Ether
  • Vinyl halide
  • Vinyl chloride
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Organonitrogen 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
StateSolid
AppearancePasty yellow mass (5).
Experimental Properties
PropertyValue
Melting Point60°C
Boiling PointNot Available
Solubility3e-06 mg/mL at 20°C [TOMLIN,C (1997)]
Predicted Properties
PropertyValueSource
Water Solubility0.00066 g/LALOGPS
logP5.93ALOGPS
logP5.59ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)10.31ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.32 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity119.31 m³·mol⁻¹ChemAxon
Polarizability40.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureInhalation (4) ; oral (4) ; dermal (4) ; eye contact (4).
Mechanism of ToxicityBoth type I and type II pyrethroids 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. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (7, 8, 4)
MetabolismThe initial step in cyfluthrin biotransformation is ester hydrolysis, giving a 3-phenoxy-4-fluorobenzyl alcohol intermediate and the permethric acid fraction. After ester hydrolysis, the 3-phenoxy-4-fluorobenzyl alcohol moiety is oxidized to the free metabolite 3-phenoxy-4-fluorobenzoic acid. This metabolite can then either be conjugated with glycine to form 3-phenoxy-4-fluorohippuric acid or hydroxylated to give 4'-hydroxy-3-phenoxy-4-fluorobenzoic acid. The metabolites as well as a small pert of the unmetabolized compound are excreted in the urine in the feces. (4, 2)
Toxicity ValuesLD50: 869-1271 mg/kg (Oral, Rat) (5) LD50: 291-609 mg/kg (Oral, Mouse) (5) L50: > 5000 mg/kg (Dermal, Rat) (5)
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 cyfluthrin 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. As for other type 2 pyrethroids, cyfluthrin produces a severe syndrome characterized by salivation and choreoathetosis. (6)
SymptomsFollowing dermal exposure to cyfluthrin, 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 cyfluthrin. 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. (3)
Concentrations
Not Available
External Links
DrugBank IDDB13828
HMDB IDHMDB0249116
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCyfluthrin
Chemspider ID94690
ChEBI ID4034
PubChem Compound ID104926
Kegg Compound IDC10982
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17912691
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18383791