Flumethrin
{{Chembox
| ImageFile = Flumethrin.svg
| ImageSize = 180px
| IUPACName = Cyano(4-fluoro-3-phenoxyphenyl)methyl 3-[2-chloro-2-(4-chlorophenyl)vinyl]-2,2-dimethylcyclopropanecarboxylate
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 69770-45-2
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2O051W13LH
| PubChem = 91702
| ChemSpiderID = 82804
| ChEMBL = 2107248
| SMILES = ClC(=CC3C(C(=O)OC(C#N)c2ccc(F)c(Oc1ccccc1)c2)C3(C)C)c4ccc(Cl)cc4
| 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
| InChIKey = YXWCBRDRVXHABN-UHFFFAOYAZ
| StdInChI = 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
| StdInChIKey = YXWCBRDRVXHABN-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=28 | H=22 | Cl=2 | F=1 | N=1 | O=3
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
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|Section6={{Chembox Pharmacology
| ATCvet = yes
| ATCCode_prefix = P53
| ATCCode_suffix = AC05
}}
|Section7={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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}}
Flumethrin is a pyrethroid insecticide.[https://drugs.ncats.io/substance/2O051W13LH FLUMETHRIN], ncats.io It is used externally in veterinary medicine against parasitic insects and ticks on cattle, sheep, goats, horses, and dogs,{{cite journal | year = 1997 | url = http://www.fao.org/docrep/W3727E/W3727E00.htm | journal = FAO Plant Production and Protection Papers | title = 4.15 Flumethrin (195) (T,R) | publisher = Food and Agriculture Organization of the United Nations}} 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.{{Cite journal | author = H. J. Schnitzerling, J. Nolan und S. Hughes | title = Toxicology and Metabolism of Isomers of Flumethrin in Larvae of Pyrethroid-Susceptilble and Resistant Strains of the Cattle Tick Boophilus microplus (Acari: Ixodidae) | journal = Experimental & Applied Acarology | volume = 6 | year = 1989 | issue = 1 | pages = 47–54 | doi = 10.1007/BF01193232| pmid = 2707107 | s2cid = 1787854 }}
Uses
Flumethrin is used in products, such as flea and tick collars, to protect pets against fleas.{{cite web | url = http://www.petparents.com/products.aspx/about/seresto?subId=howitworks | title = How Soresto Works | publisher = petparents.com}}
It is also used in the proprietary product, ″Bayvarol″, ″Polyvar Yellow″ which are veterinary treatments used by beekeepers against the parasitic mite Varroa destructor.