Tau-Fluvalinate

Basic Info

Common NameTau-Fluvalinate(F04383)
2D Structure
Description

Tau-fluvalinate is a pyrethroid insecticide. A pyrethroid is a synthetic chemical compound similar to the natural chemical pyrethrins produced by the flowers of pyrethrums (Chrysanthemum cinerariaefolium and C. coccineum). Pyrethroids are common in commercial products such as household insecticides and insect repellents. In the concentrations used in such products, they are generally harmless to human beings but can harm sensitive individuals. They are usually broken apart by sunlight and the atmosphere in one or two days, and do not significantly affect groundwater quality except for being toxic to fish. Insects with certain mutations in their sodium channel gene may be resistant to pyrethroid insecticides. (L811, L708)

FRCD IDF04383
CAS Number102851-06-9
PubChem CID91768
FormulaC26H22ClF3N2O3
IUPAC Name

[cyano-(3-phenoxyphenyl)methyl] (2R)-2-[2-chloro-4-(trifluoromethyl)anilino]-3-methylbutanoate

InChI Key

INISTDXBRIBGOC-XMMISQBUSA-N

InChI

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/t23?,24-/m1/s1

Canonical 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

Isomeric SMILES

CC(C)[C@H](C(=O)OC(C#N)C1=CC(=CC=C1)OC2=CC=CC=C2)NC3=C(C=C(C=C3)C(F)(F)F)Cl

Synonyms
        
            Tau-fluvalinate
        
            102851-06-9
        
            FLUVALINATE
        
            (a-RS,2R)-Fluvalinate
        
            CHEBI:39367
        
            Fluvarol
        
            Fluwarol
        
            cyano(3-phenoxyphenyl)methyl (2-chloro-4-(trifluoromethyl)phenyl)-D-valinate
        
            Mavrik EW
        
            cyano(3-phenoxyphenyl)methyl N-[2-chloro-4-(trifluoromethyl)phenyl]-D-valinate
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassDiphenylethers
Intermediate Tree NodesNot available
Direct ParentDiphenylethers
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsAlpha-amino acid ester - Diphenylether - Valine or derivatives - Diaryl ether - Alpha-amino acid or derivatives - Benzyloxycarbonyl - Trifluoromethylbenzene - Phenoxy compound - Phenol ether - Aniline or substituted anilines - Phenylalkylamine - Secondary aliphatic/aromatic amine - Fatty acid ester - Halobenzene - Chlorobenzene - Fatty acyl - Aryl halide - Aryl chloride - Amino acid or derivatives - Carboxylic acid ester - Secondary amine - Carboxylic acid derivative - Ether - Monocarboxylic acid or derivatives - Carbonitrile - Nitrile - Organofluoride - Organonitrogen compound - Organooxygen compound - Alkyl halide - Carbonyl group - Alkyl fluoride - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Organochloride - Organohalogen compound - Organic oxygen compound - Amine - Organopnictogen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Properties

Property NameProperty Value
Molecular Weight502.918
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Complexity735
Monoisotopic Mass502.127
Exact Mass502.127
XLogP7.7
Formal Charge0
Heavy Atom Count35
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Cashew nuts0120030European Union0.01*20/10/2017
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.01*20/10/2017
Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E...0154010European Union0.520/10/2017
Kaki/Japanese persimmons0161060European Union0.01*20/10/2017
Jambuls/jambolans (Acerolas/Barbados cherries, Arbutus berries, Camu camus, Carandas, Coco plums, Grumichamas/Brazil cherries, Hog plums/yellow mombins, Java apples, Otaheite gooseberries, Sea grap...0161070European Union0.01*20/10/2017
Sweet peppers/bell peppers (Chili peppers,)0231020European Union0.01*20/10/2017
Aubergines/eggplants (Antroewas/African eggplants/gboma, Ethiopian eggplants/gilo', Pepinos, Thorn apples, Turkey berries/devil's figs/pea eggplants/pea aubergines, Kangaroo apples/poroporo,)0231030European Union0.1520/10/2017
Celery leaves (Angelica (leaves and stems), Burnet, Caraway leaves, Coriander leaves, Culantro/false coriander leaves, Dill leaves, Fennel leaves, Fenugreek leaves, Herb of grace/rue, Lovage leaves...0256030European Union0.01*20/10/2017
Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L...0256080European Union0.01*20/10/2017
Brazil nuts0120020European Union0.01*20/10/2017
Citrus fruits0110000European Union0.420/10/2017
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.420/10/2017
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.420/10/2017
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.420/10/2017
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.420/10/2017
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.420/10/2017
Others (2)0110990European Union0.420/10/2017
Tree nuts0120000European Union0.01*20/10/2017
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.01*20/10/2017
Chestnuts0120040European Union0.01*20/10/2017

References

TitleJournalDatePubmed ID
Seasonal Effects and the Impact of In-Hive Pesticide Treatments on Parasite,Pathogens, and Health of Honey Bees.J Econ Entomol2018 Apr 229471479
Comparing bee species responses to chemical mixtures: Common response patterns?PLoS One2017 Jun 2228640811
Agricultural pesticides and veterinary substances in Uruguayan beeswax.Chemosphere2017 Jun28284118
Deciphering the groove binding modes of tau-fluvalinate and flumethrin with calf thymus DNA.Spectrochim Acta A Mol Biomol Spectrosc2016 Feb 1526571092
Extending standard testing period in honeybees to predict lifespan impacts ofpesticides and heavy metals using dynamic energy budget modelling.Sci Rep2016 Dec 2027995934
NEW INSIGHTS OF SIDE-EFFECTS OF TAU-FLUVALINATE ON BIOLOGICAL AGENTS AND POLLINATORS.Commun Agric Appl Biol Sci201527145571
Xenobiotic effects on intestinal stem cell proliferation in adult honey bee (Apismellifera L) workers.PLoS One2014 Mar 724608542
The impact of insecticides applied in apple orchards on the predatory miteKampimodromus aberrans (Acari: Phytoseiidae).Exp Appl Acarol2014 Mar24114337
Acaricide, fungicide and drug interactions in honey bees (Apis mellifera).PLoS One201323382869
Estimation of measurement uncertainty associated to the determination ofpesticide residues: a case study.J Environ Sci Health B2012 Sep22575007
Using video-tracking to assess sublethal effects of pesticides on honey bees(Apis mellifera L.).Environ Toxicol Chem2012 Jun22488825
Ecologically appropriate xenobiotics induce cytochrome P450s in Apis mellifera.PLoS One201222319603
New multiresidue method using solid-phase extraction and gaschromatography-micro-electron-capture detection for pesticide residues analysisin royal jelly.J Chromatogr A2008 Oct 3118804771
Determination of 23 pesticide residues in leafy vegetables using gaschromatography-ion trap mass spectrometry and analyte protectants.J Chromatogr A2008 Jul 418343389
Determination of acaricide residues in saudi arabian honey and beeswax usingsolid phase extraction and gas chromatography.J Environ Sci Health B200616393903
Application of solid-phase microextraction for the determination of pyrethroidresidues in vegetable samples by GC-MS.Anal Bioanal Chem2003 Jun12750867
Study of tau-fluvalinate persistence in honey.Pest Manag Sci2001 May11374166
Study of acaricide stability in honey. Characterization of amitraz degradationproducts in honey and beeswax.J Agric Food Chem2001 Dec11743771
First detection in Israel of fluvalinate resistance in the varroa mite usingbioassay and biochemical methods.Exp Appl Acarol2000 Jan10823355