Flumethrin

Last updated
Flumethrin
Flumethrin.svg
Names
IUPAC name
Cyano(4-fluoro-3-phenoxyphenyl)methyl 3-[2-chloro-2-(4-chlorophenyl)vinyl]-2,2-dimethylcyclopropanecarboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.067.352 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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
  • ClC(=CC3C(C(=O)OC(C#N)c2ccc(F)c(Oc1ccccc1)c2)C3(C)C)c4ccc(Cl)cc4
Properties
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).

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.

Contents

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 E/Z 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 Z configuration at the olefinic carbon-carbon double bond and 8% of the isomer with cis geometry on the cyclopropane ring and the Z 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.

See also

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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.