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Flumethrin

From Wikipedia, the free encyclopedia
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
ECHA InfoCard100.067.352Edit this at Wikidata
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 mass510.39 g·mol−1
Pharmacology
QP53AC05 (WHO)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

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

Chemistry

[edit]

Flumethrin is a complex mixture ofstereoisomers. The molecule contains threeasymmetric carbon atoms, there iscis-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

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Flumethrin is used in products, such asflea 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 miteVarroa destructor.

See also

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References

[edit]
  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.
Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
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