Flumethrin

Flumethrin
Names
	IUPAC name Cyano(4-fluoro-3-phenoxyphenyl)methyl 3-[2-chloro-2-(4-chlorophenyl)vinyl]-2,2-dimethylcyclopropanecarboxylate
Identifiers
CAS Number	69770-45-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2107248;
ChemSpider	82804;
ECHA InfoCard	100.067.352
PubChem CID	91702;
UNII	2O051W13LH ;
CompTox Dashboard (EPA)	DTXSID8058166 ;
	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
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

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

^ FLUMETHRIN, ncats.io
^ "4.15 Flumethrin (195) (T,R)". FAO Plant Production and Protection Papers. Food and Agriculture Organization of the United Nations. 1997.
^ 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.
^ "How Soresto Works". petparents.com.

[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.

[Schnitzerling-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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[2]

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Flumethrin

Contents

Chemistry

Uses

See also

References