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Fluvalinate

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Jan 8, 2022

Fluvalinate is a synthetic pyrethroidchemical 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,[citation needed] infestations that constitute a significant disease of such insects.

This article relies largely or entirely on a single source. (August 2016)
This article needs to be updated. (August 2016)
Fluvalinate
Clinical data
AHFS/Drugs.com International Drug Names
ATCvet code
Identifiers
  • [Cyano-(3-phenoxyphenyl)methyl] 2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
ECHA InfoCard 100.233.047
Chemical and physical data
Formula C26H22ClF3N2O3
Molar mass 502.92 g·mol−1
3D model (JSmol)
  • CC(C)C(C(=O)OC(C#N)C1=CC(=CC=C1)OC2=CC=CC=C2)NC3=C(C=C(C=C3)C(F)(F)F)Cl
  • 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

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Fluvalinate is a stable, nonvolatile,[1] viscous, heavy oil (technical) soluble in organic solvents.[2] 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.[3][better source needed]

. . . Fluvalinate . . .

Fluvalinate is synthesized from racemic valine [(RS)-valine], the synthesis is not diastereoselective. Thus, fluvalinate is a mixture of four stereoisomers, each about 25%.[4]

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:[2]

τ-Fluvalinate diastereomers

(R,R)-configuration

(R,S)-configuration

. . . Fluvalinate . . .

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. . . Fluvalinate . . .