Chemistry:Flumethrin

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Flumethrin
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
UNII
Properties
C28H22Cl2FNO3
Molar mass 510.39 g·mol−1
Pharmacology
1=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
Tracking categories (test):

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.

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. http://www.fao.org/docrep/W3727E/W3727E00.htm. 
  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. 
  4. ↑ "How Soresto Works". petparents.com. http://www.petparents.com/products.aspx/about/seresto?subId=howitworks.