Fluvalinate

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Fluvalinate
Fluvalinat Structural Formula V3.svg
Clinical data
AHFS/Drugs.com International Drug Names
ATCvet code
Identifiers
CAS Number
PubChem CID
ChemSpider
KEGG
ECHA InfoCard 100.233.047 Edit this at Wikidata
Chemical and physical data
Formula C26H22ClF3N2O3
Molar mass 502.913 g/mol
3D model (JSmol)
 NoYesY (what is this?)  (verify)

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,[citation needed] 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?][citation needed]

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 needed]

Stereoisomerism[edit]

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)-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:[2]

τ-Fluvalinate

(2 diastereomers)

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

See also[edit]

References[edit]

  1. ^ "tau-fluvalinate", Pesticide Properties DataBase, University of Hertfordshire, retrieved June 24, 2017 
  2. ^ a b "Tau-fluvalinate", PubChem. The Open Chemistry Database, National Institutes of Health, retrieved June 24, 2017 
  3. ^ MAF Biosecurity New Zealand (2001). "A Review of Treatment Options for Control of Varroa Mite in New Zealand [HortResearch Client Report No. 2001/249]" (PDF). Retrieved 28 August 2016. 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 needed]
  4. ^ David M. Whitacre (2012) (in German), [[1], p. 125, at Google Books Reviews of environmental contamination and toxicology], Springer, p. 125, ISBN 978-1-4614-3280-7, [2], p. 125, at Google Books 

Further reading[edit]

External links[edit]