Fluvalinate

Last updated
Fluvalinate
Fluvalinat Structural Formula V3.svg
Clinical data
AHFS/Drugs.com International Drug Names
ATCvet code
Identifiers
  • [Cyano-(3-phenoxyphenyl)methyl] 2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.233.047 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C26H22ClF3N2O3
Molar mass 502.92 g·mol−1
3D model (JSmol)
  • CC(C)C(Nc1ccc(C(F)(F)F)cc1Cl)C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1
  • 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 X mark.svgN
  • Key:INISTDXBRIBGOC-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (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), commonly used to control Varroa mites in honey bee colonies,[ citation needed ] infestations that constitute a significant disease of such insects.

Contents

Fluvalinate is a stable, nonvolatile, [3] viscous, heavy oil (technical) soluble in organic solvents. [4] 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. [5] [ better source needed ]

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%. [6]

Fluvalinate stereoisomers
(R,R)-Fluvalinat Structural Formula V1.svg
(R,R)-configuration
(S,S)-Fluvalinat Structural Formula V1.svg
(S,S)-configuration
(S,R)-Fluvalinat Structural Formula V1.svg
(S,R)-configuration
(R,S)-Fluvalinat Structural Formula V1.svg
(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: [4]

τ-Fluvalinate diastereomers
(R,R)-Fluvalinat Structural Formula V1.svg
(R,R)-configuration
(R,S)-Fluvalinat Structural Formula V1.svg
(R,S)-configuration

See also

Related Research Articles

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<i>Varroa destructor</i> Species of mite

Varroa destructor, the Varroa mite, is an external parasitic mite that attacks and feeds on honey bees and is one of the most damaging honey bee pests in the world. A significant mite infestation leads to the death of a honey bee colony, usually in the late autumn through early spring. Without management for Varroa mite, honey bee colonies typically collapse within 2 to 3 years in temperate climates. These mites can infest Apis mellifera, the western honey bee, and Apis cerana, the Asian honey bee. Due to very similar physical characteristics, this species was thought to be the closely related Varroa jacobsoni prior to 2000, but they were found to be two separate species after DNA analysis.

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<span class="mw-page-title-main">Colony collapse disorder</span> Aspect of apiculture

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<span class="mw-page-title-main">Beekeeping in Australia</span> Overview of beekeeping in Australia

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<span class="mw-page-title-main">Fenpropathrin</span> Chemical compound

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<i>Slow bee paralysis virus</i> Species of virus

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<span class="mw-page-title-main">Mite biting bees</span>

Mite Biting Is one of the behavioral mechanisms of honey bees used to fight off the ectoparasitic mites Varroa destructor. This behavior has been studied since the late 1990s for honey bee breeding and improvement of honeybee stocks towards mite resistance. Krispn Given and Dr. Greg Hunt at Purdue University started a hierarchical selective breeding program in 1997–present for increased mite-biting and grooming behavior of European honey bee. A group of Midwest bee breeders visiting the Purdue bee lab were inspired to start the Heartland Honey Bee Breeders Cooperative as a result of their pioneering work.

References

  1. "Fluvalinate - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2023-11-03.
  2. "Apistan: Varroa Control". Vita Bee Health. 2023-06-28. Retrieved 2023-11-03.
  3. "tau-fluvalinate", Pesticide Properties DataBase, University of Hertfordshire, retrieved June 24, 2017
  4. 1 2 "Tau-fluvalinate", PubChem. The Open Chemistry Database, National Institutes of Health, retrieved June 24, 2017
  5. 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), archived from the original (PDF) on 2016-09-11, 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.
  6. Whitacre DM (2012). Reviews of environmental contamination and toxicology. Springer. p. 125. ISBN   978-1-4614-3280-7.

Further reading