{{Short description|Insecticide and acaricide}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = changed | verifiedrevid = 431991211 | IUPAC_name = [Cyano-(3-phenoxyphenyl)methyl] 2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate | image = Fluvalinat Structural Formula V3.svg | image_class = skin-invert-image | caption = Fluvalinate molecular structure. Asterisks mark the chiral centers.
<!--Clinical data--> | tradename = Apistan, Mavrik, others | Drugs.com = {{drugs.com|international|fluvalinate}} | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 69409-94-5 | CAS_supplemental = <br />{{CAS|102851-06-9}} (tau-fluvalinate) | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 364G5G03VC | ATCvet = yes | ATC_prefix = P53 | ATC_suffix = AC10 | ATC_supplemental = | PubChem = 50516 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C10989 | ChEBI = 5135 | ChEMBL = 3185183 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 45805 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = INISTDXBRIBGOC-UHFFFAOYSA-N
<!--Chemical data--> | chemical_formula = | C=26 | H=22 | Cl=1 | F=3 | N=2 | O=3 | smiles = CC(C)C(Nc1ccc(C(F)(F)F)cc1Cl)C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1 }}
'''Fluvalinate'''<ref>{{cite book | vauthors = Kaneko H, Miyamoto J | chapter = Pyrethroid Chemistry and Metabolism | title = Handbook of Pesticide Toxicology | pages = 1263–1288 | date = 2001 | doi = 10.1016/B978-012426260-7.50061-6 | isbn = 978-0-12-426260-7 | quote = 58.15 τ-FLUVALINATE (FLUVALINATE) }}</ref> is a synthetic pyrethroid chemical compound contained as an active agent in the products Apistan,<ref>{{Cite web | title = Apistan: Varroa Control | date = 2023-06-28 | url = https://www.vita-europe.com/beehealth/products/apistan/ | access-date = 2023-11-03 | website = Vita Bee Health | language = en-US }}</ref> Klartan, and Minadox, that is an acaricide (specifically, a miticide), used to control ''Varroa'' mites in honey bee colonies,<ref>{{Cite web | vauthors = Bomgardner MM | title = Hope For The Bees | date = 2025-01-21 | url = https://cen.acs.org/articles/89/i13/Hope-Bees.html | access-date = 2025-08-21 | website = Chemical & Engineering News | language = en }}</ref> infestations that constitute a significant disease of such insects.
Fluvalinate is a stable, nonvolatile,<ref>{{citation |url=http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/608.htm |title=tau-fluvalinate |work=Pesticide Properties DataBase |publisher=University of Hertfordshire |accessdate=June 24, 2017}}</ref> viscous, heavy oil (technical) soluble in organic solvents.<ref name="nih">{{citation |url=https://pubchem.ncbi.nlm.nih.gov/compound/Tau-fluvalinate |title=Tau-fluvalinate |work=PubChem. The Open Chemistry Database |publisher=National Institutes of Health |accessdate=June 24, 2017}}</ref> <!-- Its effectiveness was first demonstrated in France and Israel.{{when?|date=August 2016}}{{cn|date=August 2016}} --> == 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<ref>{{Cite web | title = Fluvalinate - OEHHA | url = https://oehha.ca.gov/proposition-65/chemicals/fluvalinate | access-date = 2025-08-21 | website = oehha.ca.gov }}</ref> though there are no established chronic effects in adult humans.<ref>{{Cite web | title = Pesticide Active Ingredients Database / Home and Landscape / Statewide IPM Program | url = https://ipm.ucanr.edu/home-and-landscape/pesticide-active-ingredients-database/active-ingredient-details/?uaiKey=12#PotentialHazard | access-date = 2025-08-21 | website = ipm.ucanr.edu }}</ref>
Fluvalinate can be found in both honey and beeswax though it tends to migrate to beeswax over time due to its lipophilic nature.<ref>{{Cite journal | vauthors = Bogdanov S, Kilchenmann V, Imdorf A | title = Acaricide residues in some bee products | journal = Journal of Apicultural Research | volume = 37 | issue = 2 | pages = 57–67 | date = 1998-01-01 | doi = 10.1080/00218839.1998.11100956 | bibcode = 1998JApiR..37...57B | issn = 0021-8839 }}</ref>
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.<ref>{{cite web |title=Denmark bans more PFAS pesticides to protect groundwater |url=https://www.pan-europe.info/blog/denmark-bans-more-pfas-pesticides-protect-groundwater |publisher=Pesticide Action Network Europe |access-date=6 November 2025 |date=October 6, 2025}}</ref>
== 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%.<ref name="David M. Whitacre">{{cite book | veditors = Whitacre DM | chapter = Table B18 (tau-)Fluvalinate, technical products and mixtures | title = Reviews of Environmental Contamination and Toxicology | volume = 219 | pages = 125 | date = 2012 | doi = 10.1007/978-1-4614-3281-4 | isbn = 978-1-4614-3280-7 | chapter-url = {{GBurl | L3gpxVLsbMYC | p = 125}}}}</ref>
{| class="wikitable float-left" style="text-align:center" |- class="hintergrundfarbe6" |+ Fluvalinate stereoisomers |- | 180px|(''R'',''R'')-Fluvalinat<br /> <small>(''R'',''R'')-configuration</small> || 180px|(''S'',''S'')-Fluvalinat<br /> <small>(''S'',''S'')-configuration</small> |- | 180px|(''S'',''R'')-Fluvalinat<br /> <small>(''S'',''R'')-configuration</small> || 180px|(''R'',''S'')-Fluvalinat<br /> <small>(''R'',''S'')-configuration</small> |}
''Tau''-fluvalinate (τ-fluvalinate) is the trivial name for (2''R'')-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:<ref name="nih" /> {| class="wikitable float-left" style="text-align:center" |- class="hintergrundfarbe6" |+ τ-Fluvalinate diastereomers |- | 180px|(''R'',''R'')-Fluvalinat<br /> <small>(''R'',''R'')-configuration</small> || 180px|(''R'',''S'')-Fluvalinat<br /> <small>(''R'',''S'')-configuration</small> |}
== See also == * Diseases of the honey bee
== References == {{reflist}}
== Further reading == {{refbegin}} * {{cite web | vauthors = Bessin R | title = Varroa Mites Infesting Honey Bee Colonies [Insect & Pest Info, Home & Health Pests, ENTFACT-608, April 2016 revision] | location = North Lexington, KY | year = 2016 | publisher = University of Kentucky, Department of Entomology | url = https://entomology.ca.uky.edu/ef608 | access-date = 28 August 2016 | quote = 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. }} {{refend}}
== External links == * [https://archive.today/20121212092305/http://www.epa.gov/EPA-PEST/2005/November/Day-16/p22616.htm EPA: Tau-fluvalinate; Reregistration Eligibility Decision for Low Risk Pesticide; Notice of Availability] * {{PPDB|608|Name=Tau-fluvalinate}} * {{PPDB|1720|Name=Fluvalinate}} * [https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/241336 ECHA]
{{insecticides}}
Category:1-chloro-3-(trifluoromethyl)benzene derivatives Category:(cyano-(3-phenoxyphenyl)methyl) 3-methylbutanoates Category:Isopropyl compounds