Flumethrin

Flumethrin is a pyrethroid insecticide.[1] It is used externally in veterinary medicine against parasitic insects and ticks on cattle, sheep, goats, horses, and dogs,[2] and the treatment of parasitic mites in honeybee colonies.

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^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2107248
ChemSpider	82804
ECHA InfoCard	100.067.352
PubChem CID	91702
UNII	2O051W13LH^Y
CompTox Dashboard (EPA)	DTXSID8058166
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 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[3]

Uses

Flumethrin is used in products, such as flea and tick collars, to protect pets against fleas.[4]

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

References

1. Flumethrin, drugs.com
2. "4.15 Flumethrin (195) (T,R)". FAO Plant Production and Protection Papers. Food and Agriculture Organization of the United Nations. 1997.
3. H. J. Schnitzerling, J. Nolan und S. Hughes (1989). "Toxicology and Metabolism of Isomers of Flumethrin in Larvae of Pyrethroid-Susceptilble and Resistant Strains of the Cattle Tick Boophilus microplus (Acari: Ixodidae)". Experimental & Applied Acarology. 6: 47–54. doi:10.1007/BF01193232.
4. "How Soresto Works". petparents.com.