Fluvalinate

Fluvalinate

Clinical data
AHFS/Drugs.com	International Drug Names
ATCvet code	QP53AC10 (WHO)
Identifiers
IUPAC name [Cyano-(3-phenoxyphenyl)methyl] 2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate
CAS Number	69409-94-5 N 102851-06-9 (tau-fluvalinate)
PubChem CID	50516
ChemSpider	45805 N
UNII	364G5G03VC
KEGG	C10989 Y
ChEBI	CHEBI:5135
ChEMBL	ChEMBL3185183
CompTox Dashboard (EPA)	DTXSID7024110
ECHA InfoCard	100.233.047
Chemical and physical data
Formula	C26H22ClF3N2O3
Molar mass	502.92 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)C(Nc1ccc(C(F)(F)F)cc1Cl)C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1
InChI InChI=1S/C26H22ClF3N2O3/c1-16(2)24(32-22-12-11-18(14-21(22)27)26(28,29)30)25(33)35-23(15-31)17-7-6-10-20(13-17)34-19-8-4-3-5-9-19/h3-14,16,23-24,32H,1-2H3 N Key:INISTDXBRIBGOC-UHFFFAOYSA-N N
NY (what is this?)  (verify)

Fluvalinate is a synthetic pyrethroid chemical compound contained as an active agent in the products Apistan, Klartan, and Minadox, that is an acaricide (specifically, a miticide), commonly used to control Varroa mites in honey bee colonies, infestations that constitute a significant disease of such insects.

Fluvalinate is a stable, nonvolatile, viscous, heavy oil (technical) soluble in organic solvents. Although the compound may be found in drones, a study has found honey samples virtually absent of fluvalinate, on account of its affinity to beeswax.

Stereoisomerism

Fluvalinate is synthesized from racemic valine [(RS)-valine], the synthesis is not diastereoselective. Thus, fluvalinate is a mixture of four stereoisomers, each about 25%.

Fluvalinate stereoisomers
(R,R)-configuration
(S,S)-configuration
(S,R)-configuration
(R,S)-configuration

Tau-fluvalinate (τ-fluvalinate) is the trivial name for (2R)-fluvalinate. The C atom in the valinate structure is in (R)-absolute configuration, while the second chiral atom is a mixture of (R)- and (S)-configurations:

τ-Fluvalinate diastereomers
(R,R)-configuration
(R,S)-configuration

See also

• Diseases of the honey bee

Further reading

• Bessin R (2016). "Varroa Mites Infesting Honey Bee Colonies [Insect & Pest Info, Home & Health Pests, ENTFACT-608, April 2016 revision]". North Lexington, KY: University of Kentucky, Department of Entomology. Retrieved 28 August 2016. Apistan is a product available that will kill the mites and cause the mites to drop from the bees. … Apistan strips, which contain the miticide fluvalinate, are available from most large beekeeping suppliers and can be used both for detection and treatment of varroa infestations.

External links

• EPA: Tau-fluvalinate; Reregistration Eligibility Decision for Low Risk Pesticide; Notice of Availability
• Tau-fluvalinate in the Pesticide Properties DataBase (PPDB)
• Fluvalinate in the Pesticide Properties DataBase (PPDB)