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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.067.352
PubChem CID
UNII
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
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″, ″Polyvar Yellow″ which are veterinary treatments used by beekeepers against the parasitic mite Varroa destructor.

References
  1. FLUMETHRIN, ncats.io
  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 (1): 47–54. doi:10.1007/BF01193232. PMID 2707107. S2CID 1787854.
  4. "How Soresto Works". petparents.com.


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