Fluvalinate

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Wikipedia

Fluvalinate
Fluvalinate molecular structure. Asterisks mark the chiral centers.
Clinical data
Trade namesApistan, Mavrik, others
AHFS/Drugs.comInternational 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 InfoCard100.233.047 Edit this at Wikidata
Chemical and physical data
FormulaC26H22ClF3N2O3
Molar mass502.92 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 ☒N
  • Key:INISTDXBRIBGOC-UHFFFAOYSA-N ☒N
 ☒NcheckY (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), used to control Varroa mites in honey bee colonies,[3] infestations that constitute a significant disease of such insects.

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

See also

References

  1. ↑ Kaneko H, Miyamoto J (2001). "Pyrethroid Chemistry and Metabolism". Handbook of Pesticide Toxicology. pp. 1263–1288. doi:10.1016/B978-012426260-7.50061-6. ISBN 978-0-12-426260-7. 58.15 τ-FLUVALINATE (FLUVALINATE)
  2. ↑ "Apistan: Varroa Control". Vita Bee Health. 2023-06-28. Retrieved 2023-11-03.
  3. ↑ Bomgardner MM (2025-01-21). "Hope For The Bees". Chemical & Engineering News. Retrieved 2025-08-21.
  4. ↑ "tau-fluvalinate", Pesticide Properties DataBase, University of Hertfordshire, retrieved June 24, 2017
  5. 1 2 "Tau-fluvalinate", PubChem. The Open Chemistry Database, National Institutes of Health, retrieved June 24, 2017
  6. ↑ Bogdanov S, Kilchenmann V, Imdorf A (1998-01-01). "Acaricide residues in some bee products". Journal of Apicultural Research. 37 (2): 57–67. doi:10.1080/00218839.1998.11100956. ISSN 0021-8839.
  7. ↑ "Fluvalinate - OEHHA". oehha.ca.gov. Retrieved 2025-08-21.
  8. ↑ "Pesticide Active Ingredients Database / Home and Landscape / Statewide IPM Program". ipm.ucanr.edu. Retrieved 2025-08-21.
  9. ↑ Whitacre DM, ed. (2012). "Table B18 (tau-)Fluvalinate, technical products and mixtures". Reviews of Environmental Contamination and Toxicology. Vol. 219. p. 125. doi:10.1007/978-1-4614-3281-4. ISBN 978-1-4614-3280-7.

Further reading