Fluvalinate

Last updated
Fluvalinate
Fluvalinat Structural Formula V3.svg
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
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.233.047 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C26H22ClF3N2O3
Molar mass 502.92 g·mol−1
3D model (JSmol)
  • CC(C)C(Nc1ccc(C(F)(F)F)cc1Cl)C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1
  • 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 X mark.svgN
  • Key:INISTDXBRIBGOC-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (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,[ citation needed ] infestations that constitute a significant disease of such insects.

Contents

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 ]

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)-Fluvalinat Structural Formula V1.svg
(R,R)-configuration
(S,S)-Fluvalinat Structural Formula V1.svg
(S,S)-configuration
(S,R)-Fluvalinat Structural Formula V1.svg
(S,R)-configuration
(R,S)-Fluvalinat Structural Formula V1.svg
(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)-Fluvalinat Structural Formula V1.svg
(R,R)-configuration
(R,S)-Fluvalinat Structural Formula V1.svg
(R,S)-configuration

See also


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References

  1. "tau-fluvalinate", Pesticide Properties DataBase, University of Hertfordshire, retrieved June 24, 2017
  2. 1 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