Fluvalinate

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), used to control Varroa mites in honey bee colonies,^[3] infestations that constitute a significant disease of such insects.

Fluvalinate

Fluvalinate molecular structure. Asterisks mark the chiral centers.
Clinical data
Trade names	Apistan, Mavrik, others
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 stable, nonvolatile,^[4] viscous, heavy oil (technical) soluble in organic solvents.^[5] Fluvalinate can be found in both honey and beeswax though it tends to migrate to beeswax over time due to its lipophilic nature.^[6]

Toxicity

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

The chemical is fatal if inhaled and is extremely toxic to aquatic life. Hazard codes indicate fluvalinate is both an acute and long-term toxic hazard in aquatic systems. It is considered a developmental hazard^[7] though there are no established chronic effects in adult humans.^[8]

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%.^[9]

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:^[5]

τ-Fluvalinate diastereomers

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

See also

• Diseases of the honey bee