| Revision as of 12:39, 1 June 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref') per Chem/Drugbox validation (report [[Wik← Previous edit |
Latest revision as of 22:26, 15 December 2024 edit undoDavid coder11 (talk | contribs)2 editsm Added paragraph for CHS Health ClassificationTags: Visual edit Newcomer task Newcomer task: update |
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{{Short description|Chemical compound}} |
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{{update|date=August 2016}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 431793757 |
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| verifiedrevid = 431991211 |
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| IUPAC_name = 2--3-methylbutanoate |
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| IUPAC_name = 2--3-methylbutanoate |
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| image = Fluvalinate structure.svg |
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| image = Fluvalinat Structural Formula V3.svg |
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| CAS_number = |
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| CAS_supplemental = <br />{{CAS|102851-06-9}} (tau-fluvalinate) |
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<!--Clinical data--> |
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| ATCvet = yes |
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| tradename = |
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| ATC_prefix = P53 |
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| Drugs.com = {{drugs.com|international|fluvalinate}} |
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| ATC_suffix = AC10 |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| ATC_supplemental = |
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| PubChem = 50516 |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| DrugBank = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = 69409-94-5 |
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| CAS_supplemental = <br />{{CAS|102851-06-9}} (tau-fluvalinate) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 364G5G03VC |
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| ATCvet = yes |
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| ATC_prefix = P53 |
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| ATC_suffix = AC10 |
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| ATC_supplemental = |
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| PubChem = 50516 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C18790 |
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| KEGG = C10989 |
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| ChEBI = 5135 |
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| chemical_formula = |
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| ChEMBL = 3185183 |
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| C=26 | H=22 | Cl=1 | F=3 | N=2 | O=3 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| molecular_weight = 502.913 g/mol |
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| ChemSpiderID = 45805 |
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| smiles = CC(C)C(C(=O)OC(C#N)C1=CC(=CC=C1)OC2=CC=CC=C2)NC3=C(C=C(C=C3)C(F)(F)F)Cl |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| bioavailability = |
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| 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 |
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| protein_bound = |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| metabolism = |
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| StdInChIKey = INISTDXBRIBGOC-UHFFFAOYSA-N |
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| elimination_half-life = |
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| excretion = |
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<!--Chemical data--> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| chemical_formula = |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| C=26 | H=22 | Cl=1 | F=3 | N=2 | O=3 |
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| pregnancy_category= |
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| smiles = CC(C)C(Nc1ccc(C(F)(F)F)cc1Cl)C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1 |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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}} |
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}} |
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'''Fluvalinate'''<ref>{{Cite web |title=Fluvalinate - an overview {{!}} ScienceDirect Topics |url=https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/fluvalinate |access-date=2023-11-03 |website=www.sciencedirect.com}}</ref> is a synthetic ] chemical compound contained as an active agent in the products Apistan,<ref>{{Cite web |date=2023-06-28 |title=Apistan: Varroa Control |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 ]), commonly used to control ] in ] colonies,{{cn|date=August 2016}} infestations that constitute a significant ]. |
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'''Fluvalinate''' (trade names include '''Apistan''', '''Klartan''', '''Minadox''') is a synthetic ] commonly used to control ] in ] colonies. |
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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}} |
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Fluvalinate is a stable, non-volatile, fat-soluble compound. Fluvalinate effectiveness was demonstrated in France and Israel. 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.<ref>''A Review of Treatment Options for Control of Varroa Mite in New Zealand'' http://www.biosecurity.govt.nz/pests-diseases/animals/varroa/paper/varroa-treatment-options.htm#4 MAF Biosecurity New Zealand</ref> |
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--> |
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Although the compound may be found in ], a study has found ] samples virtually absent of fluvalinate, on account of its affinity to ].<ref>{{citation | author = MAF Biosecurity New Zealand | date = 2001 | title = A Review of Treatment Options for Control of Varroa Mite in New Zealand | url = http://www.biosecurity.govt.nz/files/pests/varroa/papers/varroa-treatment-options.pdf | access-date = 28 August 2016 | quote = 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. | archive-url=https://web.archive.org/web/20160911015922/http://www.biosecurity.govt.nz/files/pests/varroa/papers/varroa-treatment-options.pdf | archive-date=2016-09-11 | url-status=dead}}</ref>{{better source|date=August 2016}} |
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== CHS Health Classification == |
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'''Tau-fluvalinate''' (τ-fluvalinate) is the trivial name for (2''R'')-fluvalinate. |
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Fluvalinate is considered an acute toxic, Health hazard and environmental hazard by ECHA (]). |
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The chemical is fatal if inhaled and is extremally toxic to aquatic life. If not fatal the effects are permanent and has multiple long lasting effects. |
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==See also== |
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* |
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== Stereoisomerism == |
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==References== |
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Fluvalinate is synthesized from ] valine , the synthesis is not diastereoselective. Thus, fluvalinate is a mixture of four stereoisomers, each about 25%.<ref name="David M. Whitacre">{{cite book | vauthors = Whitacre DM |title=Reviews of environmental contamination and toxicology|publisher=Springer|page=125|isbn=978-1-4614-3280-7|date=2012|language=en|url={{Google books|L3gpxVLsbMYC&pg||page=125|plainurl=yes}} |
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}}</ref> |
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{| class="wikitable float-left" style="text-align:center" |
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|- class="hintergrundfarbe6" |
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|+ Fluvalinate stereoisomers |
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|- |
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| ]<br /> <small>(''R,R'')-configuration</small> |
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|| ]<br /> <small>(''S,S'')-configuration</small> |
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|- |
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| ]<br /> <small>(''S,R'')-configuration</small> |
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|| ]<br /> <small>(''R,S'')-configuration</small> |
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|} |
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''Tau''-fluvalinate (τ-fluvalinate) is the trivial name for (2''R'')-fluvalinate. The C atom in the valinate structure is in (''R'')-], while the second chiral atom is a mixture of (''R'')- and (''S'')-configurations:<ref name="nih" /> |
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{| class="wikitable float-left" style="text-align:center" |
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|- class="hintergrundfarbe6" |
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|+ τ-Fluvalinate diastereomers |
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|- |
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| ]<br /> <small>(''R,R'')-configuration</small> |
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|| ]<br /> <small>(''R,S'')-configuration</small> |
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|} |
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== See also == |
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<!--already linked * ] |
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* ] |
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* ] --> |
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* ] |
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== References == |
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{{reflist}} |
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{{reflist}} |
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== Further reading == |
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* {{cite web | vauthors = Bessin R | year = 2016 | title = Varroa Mites Infesting Honey Bee Colonies | location = North Lexington, KY | publisher = University of Kentucky, Department of Entomology | url = https://entomology.ca.uky.edu/ef608 | access-date = 28 August 2016 | quote = <small> 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.</small> }} |
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== External links == |
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* |
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* {{PPDB|608|Name=Tau-fluvalinate}} |
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* {{PPDB|1720|Name=Fluvalinate}} |
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* |
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{{insecticides}} |
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