Fluvalinate

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
Clinical data
AHFS/Drugs.comInternational Drug Names
ATCvet code
Identifiers
IUPAC name
  • [Cyano-(3-phenoxyphenyl)methyl] 2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.233.047
Chemical and physical data
FormulaC26H22ClF3N2O3
Molar mass502.92 g·mol−1
3D model (JSmol)
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,[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]

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%.[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

See also
  • Diseases of the honey bee


References
  1. "tau-fluvalinate", Pesticide Properties DataBase, University of Hertfordshire, retrieved June 24, 2017
  2. "Tau-fluvalinate", PubChem. The Open Chemistry Database, National Institutes of Health, retrieved June 24, 2017
  3. MAF Biosecurity New Zealand (2001). "A Review of Treatment Options for Control of Varroa Mite in New Zealand [HortResearch Client Report No. 2001/249]" (PDF). Archived from the original (PDF) on 2016-09-11. Retrieved 28 August 2016. This report was commissioned by MAF to aid in internal decision making only. This report in no way constitutes MAF's advice to beekeepers and is useful only as background information. {{cite journal}}: Cite journal requires |journal= (help)
  4. Whitacre DM (2012). Reviews of environmental contamination and toxicology. Springer. p. 125. ISBN 978-1-4614-3280-7.

Further reading
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