Fluvalinate

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 ^[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]

Health and Environmental Impacts

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 ^[6] though there are no established chronic effects in adult humans. ^[7]

Fluvalinate can be found in both honey and beeswax though it tends to migrate to beeswax over time due to its lipophilic nature. ^[8]

Pesticide products containing fluvalinate have been banned in Denmark because the chemical can degrade into trifluoroacetic acid, which can then contaminate groundwater and not decompose. ^[9]

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%. ^[10]

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

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. "Tau-fluvalinate", PubChem. The Open Chemistry Database, National Institutes of Health, retrieved June 24, 2017
6. "Fluvalinate - OEHHA". oehha.ca.gov. Retrieved 2025-08-21.
7. "Pesticide Active Ingredients Database / Home and Landscape / Statewide IPM Program". ipm.ucanr.edu. Retrieved 2025-08-21.
8. Bogdanov S, Kilchenmann V, Imdorf A (1998-01-01). "Acaricide residues in some bee products". Journal of Apicultural Research. 37 (2): 57–67. Bibcode:1998JApiR..37...57B. doi:10.1080/00218839.1998.11100956. ISSN   0021-8839.
9. "Denmark bans more PFAS pesticides to protect groundwater". Pesticide Action Network Europe. October 6, 2025. Retrieved 6 November 2025.
10. 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

• Bessin R (2016). "Varroa Mites Infesting Honey Bee Colonies [Insect & Pest Info, Home & Health Pests, ENTFACT-608, April 2016 revision]". North Lexington, KY: University of Kentucky, Department of Entomology. Retrieved 28 August 2016. Apistan is a product available that will kill the mites and cause the mites to drop from the bees. … Apistan strips, which contain the miticide fluvalinate, are available from most large beekeeping suppliers and can be used both for detection and treatment of varroa infestations.

External links

• EPA: Tau-fluvalinate; Reregistration Eligibility Decision for Low Risk Pesticide; Notice of Availability
• Tau-fluvalinate in the Pesticide Properties DataBase (PPDB)
• Fluvalinate in the Pesticide Properties DataBase (PPDB)
• ECHA