This article needs to be updated. Please help update this article to reflect recent events or newly available information. (August 2016)

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 NCategory:Articles with changed CASNo identifier 102851-06-9 (tau-fluvalinate)
PubChem CID	50516
ChemSpider	45805 NCategory:Articles with changed ChemSpider identifier
UNII	364G5G03VC
KEGG	C10989 Y
ChEBI	CHEBI:5135
ChEMBL	ChEMBL3185183
CompTox Dashboard (EPA)	DTXSID7024110
ECHA InfoCard	100.233.047 Category:ECHA InfoCard ID from Wikidata#*
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 NCategory:Articles with changed InChI identifier Key:INISTDXBRIBGOC-UHFFFAOYSA-N NCategory:Articles with changed InChI identifier
NY (what is this?)  (verify)

Fluvalinate^[1] is a synthetic pyrethroid chemical compound contained as an active agent in the products Apistan,^[2] Klartan, and Minadox, that is an acaricide (specifically, a miticide), commonly used to control Varroa mites in honey bee colonies,Category:All articles with unsourced statementsCategory:Articles with unsourced statements from August 2016^{[citation needed]} infestations that constitute a significant disease of such insects.

Fluvalinate is a stable, nonvolatile,^[3] viscous, heavy oil (technical) soluble in organic solvents.^[4] 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.^[5]Category:All articles lacking reliable referencesCategory:Articles lacking reliable references from August 2016^{[better source needed]}

CHS Health Classification

Fluvalinate is considered an acute toxic, Health hazard and environmental hazard by ECHA (European Chemicals Agency).

The chemical is fatal if inhaled and is extremally toxic to aquatic life. If not fatal the effects are permanent and has multiple long lasting effects.

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%.^[6]

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:^[4]

τ-Fluvalinate diastereomers

(R,R)-configuration	(R,S)-configuration

See also

• Diseases of the honey bee

References

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)
• ECHA