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词条 Fluvalinate
释义

  1. Stereoisomerism

  2. See also

  3. References

  4. Further reading

  5. External links

{{one source|date=August 2016}}{{update|date=August 2016}}{{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
| tradename =
| Drugs.com = {{drugs.com|international|fluvalinate}}
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| legal_CA =
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| routes_of_administration =
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| excretion =
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 69409-94-5
| CAS_supplemental =
{{CAS|102851-06-9}} (tau-fluvalinate)
| ATCvet = yes
| ATC_prefix = P53
| ATC_suffix = AC10
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| PubChem = 50516
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| KEGG = C18790
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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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| StdInChIKey = INISTDXBRIBGOC-UHFFFAOYSA-N
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| C=26 | H=22 | Cl=1 | F=3 | N=2 | O=3
| molecular_weight = 502.913 g/mol
| 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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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), that is commonly used to control varroa mites in honey bee colonies,{{cn|date=August 2016}} infestations that constitute a significant disease of such insects.

Fluvalinate is a stable, non-volatile[1], viscous heavy oil (technical) soluble in organic solvents.[2] Its effectiveness was first demonstrated in France and Israel.{{when?|date=August 2016}}{{cn|date=August 2016}}

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|date=August 2016}}

Stereoisomerism

Fluvalinate is synthesized from racemic valine [(RS)-valine], the synthesis is not diastereoselective. Thus, fluvinate is a mixture of four stereoisomers, each approx. 25 %.[4]

Fluvalinate

(4 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:[2]
τ-Fluvalinate

(2 diastereomers)


(R,R)-configuration

(R,S)-configuration

See also

  • Acaricide
  • Pyrethroid
  • Varroa destructor
  • Diseases of the honey bee
{{colend}}

References

1. ^{{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}}
2. ^{{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}}
3. ^{{cite journal | author = MAF Biosecurity New Zealand | date = 2001 | title = A Review of Treatment Options for Control of Varroa Mite in New Zealand [HortResearch Client Report No. 2001/249] | 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.}}{{better source|date=August 2016}}
4. ^{{citation|surname1=David M. Whitacre|title=Reviews of environmental contamination and toxicology|publisher=Springer|page=125|isbn=978-1-4614-3280-7|date=2012|language=German|url={{Google books|L3gpxVLsbMYC&pg||page=125}}}}

Further reading

  • {{cite web | author = Bessin, Ric | year = 2016 | title = Varroa Mites Infesting Honey Bee Colonies [Insect & Pest Info, Home & Health Pests, ENTFACT-608, April 2016 revision] | location = North Lexington, KY | 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. }}

External links

  • EPA: Tau-fluvalinate; Reregistration Eligibility Decision for Low Risk Pesticide; Notice of Availability
  • {{PPDB|608|Name=Tau-fluvalinate}}
  • {{PPDB|1720|Name=Fluvalinate}}
{{antiinfective-drug-stub}}

6 : Pyrethroids|Chloroarenes|Trifluoromethyl compounds|Nitriles|Phenol ethers|Cyanohydrin esters

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