Basic Info

Common NameFlumethrin(F04382)
2D Structure
Description

Flumethrin is an alpha-cyano-3-phenoxyphenyl pyrethroid insecticide used in the control of ectoparasites on cattle, sheep, goats, horses, and dogs. It is formulated as a 6% solution for use as a spray or dip and as a 1% solution for the pour-on treatment of cattle. In addition, flumethrin is marketed as strips for the diagnosis and control of varroatosis in bee hives. 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. (L811, L708, L857, L885)

FRCD IDF04382
CAS Number69770-45-2
PubChem CID6033664
FormulaC28H22Cl2FNO3
IUPAC Name

[cyano-(4-fluoro-3-phenoxyphenyl)methyl] 3-[(Z)-2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylate

InChI Key

YXWCBRDRVXHABN-JCMHNJIXSA-N

InChI

InChI=1S/C28H22Cl2FNO3/c1-28(2)21(15-22(30)17-8-11-19(29)12-9-17)26(28)27(33)35-25(16-32)18-10-13-23(31)24(14-18)34-20-6-4-3-5-7-20/h3-15,21,25-26H,1-2H3/b22-15-

Canonical SMILES

CC1(C(C1C(=O)OC(C#N)C2=CC(=C(C=C2)F)OC3=CC=CC=C3)C=C(C4=CC=C(C=C4)Cl)Cl)C

Isomeric SMILES

CC1(C(C1C(=O)OC(C#N)C2=CC(=C(C=C2)F)OC3=CC=CC=C3)/C=C(/C4=CC=C(C=C4)Cl)\Cl)C

Synonyms
        
            Cyano(4-fluoro-3-phenoxyphenyl)methyl 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarboxylate
        
            Flumethrin
        
            69770-45-2
        
            Flumethrin [BAN]
        
            Flumethrin (BAN)
        
            EINECS 274-110-4
        
            AI3-29751
        
            CHEBI:39361
        
            C28H22Cl2FNO3
        
            Bayticol
        
Classifies
                

                  
                    Veterinary Drug
                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassFatty Acyls
SubclassFatty acid esters
Intermediate Tree NodesNot available
Direct ParentPyrethroids
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPyrethroid skeleton - Diphenylether - Diaryl ether - Benzyloxycarbonyl - Phenoxy compound - Phenol ether - Styrene - Chlorobenzene - Fluorobenzene - Halobenzene - Aryl chloride - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Cyclopropanecarboxylic acid or derivatives - Benzenoid - Carboxylic acid ester - Vinyl halide - Vinyl chloride - Haloalkene - Chloroalkene - Nitrile - Carbonitrile - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Ether - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organooxygen compound - Organohalogen compound - Organochloride - Organic nitrogen compound - Organofluoride - Aromatic homomonocyclic compound
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight510.386
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Complexity825
Monoisotopic Mass509.096
Exact Mass509.096
XLogP7.6
Formal Charge0
Heavy Atom Count35
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count3
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
HoneyJapan0.005ppm
Other Aquatic AnimalJapan0.005ppm
CrustaceansJapan0.005ppm
Shelled MolluscasJapan0.005ppm
Other FishJapan0.005ppm
PerciformesJapan0.005ppm
AnguilliformesJapan0.005ppm
SalmoniformesJapan0.005ppm
Other Poultry,EggsJapan0.03ppm
Chicken,EggsJapan0.03ppm
Other Poultry Animals,Edible OffalJapan0.005ppm
Chicken,Edible OffalJapan0.03ppm
Other Poultry Animals,KidneyJapan0.005ppm
Chicken,KidneyJapan0.03ppm
Other Poultry Animals,LiverJapan0.005ppm
Chicken,LiverJapan0.03ppm
Other Poultry Animals,FatJapan0.005ppm
Chicken,FatJapan0.03ppm
Other Poultry Animals,MuscleJapan0.005ppm
Chicken,MuscleJapan0.03ppm

References

TitleJournalDatePubmed ID
Occurrence and Health Risk of Patulin and Pyrethroids in Fruit Juices Consumed in Bangkok, Thailand.J Food Prot2017 Sep28762777
Deciphering the groove binding modes of tau-fluvalinate and flumethrin with calf thymus DNA.Spectrochim Acta A Mol Biomol Spectrosc2016 Feb 1526571092