Flumethrin

Flumethrin

Names
IUPAC name Cyano(4-fluoro-3-phenoxyphenyl)methyl 3-[2-chloro-2-(4-chlorophenyl)vinyl]-2,2-dimethylcyclopropanecarboxylate
Identifiers
CAS Number	69770-45-2
ChEMBL	ChEMBL2107248
ChemSpider	82804
Jmol 3D model	Interactive image
PubChem	91702
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 Key: YXWCBRDRVXHABN-UHFFFAOYSA-N InChI=1/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 Key: YXWCBRDRVXHABN-UHFFFAOYAZ
SMILES ClC(=CC3C(C(=O)OC(C#N)c2ccc(F)c(Oc1ccccc1)c2)C3(C)C)c4ccc(Cl)cc4
Properties
Chemical formula	C28H22Cl2FNO3
Molar mass	510.39 g·mol−1
Pharmacology
ATCvet code	QP53AC05
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Flumethrin is a pyrethroid insecticide. It is used externally in veterinary medicine against parasitic insects and ticks on cattle, sheep, goats, horses, and dogs, and the treatment of parasitic mites in honeybee colonies.

Chemistry

Flumethrin is a complex mixture of stereoisomers. The molecule contains three asymmetric carbon atoms, there is cis-trans isomerism at the cyclopropane ring, and cis-trans isomerism at the carbon-carbon double bond of the alkene. So there are 16 different isomers. Commercial flumethrin typically contains 92% of the trans isomers on the cyclopropane ring and the cis-configuration at the olefinic carbon-carbon double bond and 8% of the isomer with cis geometry on the cyclopropane ring and the cis-configuration at the olefinic carbon-carbon double bond.

Uses

Flumethrin is used in products, such as flea and tick collars, to protect pets against fleas.

It is also used in the proprietary product, Bayvarol, which is a veterinary treatment used by beekeepers against the parasitic mite Varroa destructor.