Trifloxystrobin

Basic Info

Common NameTrifloxystrobin(F05449)
2D Structure
Description

Trifloxystrobin is a foliar applied fungicide for cereals which is particularly active against Ascomycetes, Deuteromycetes and Oomycetes. It has a broad spectrum of action with preventative and curative action. It is a respiration inhibitor (QoL fungicide).

FRCD IDF05449
CAS Number141517-21-7
PubChem CID11664966
FormulaC20H19F3N2O4
IUPAC Name

methyl (2E)-2-methoxyimino-2-[2-[[(E)-1-[3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]acetate

InChI Key

ONCZDRURRATYFI-TVJDWZFNSA-N

InChI

InChI=1S/C20H19F3N2O4/c1-13(14-8-6-9-16(11-14)20(21,22)23)24-29-12-15-7-4-5-10-17(15)18(25-28-3)19(26)27-2/h4-11H,12H2,1-3H3/b24-13+,25-18+

Canonical SMILES

CC(=NOCC1=CC=CC=C1C(=NOC)C(=O)OC)C2=CC(=CC=C2)C(F)(F)F

Isomeric SMILES

C/C(=N\OCC1=CC=CC=C1/C(=N\OC)/C(=O)OC)/C2=CC(=CC=C2)C(F)(F)F

Synonyms
        
            Trifloxystrobin
        
            methyl (2E)-2-methoxyimino-2-[2-[[(E)-1-[3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]acetate
        
            141517-21-7
        
            CHEBI:81833
        
            CGA 279202
        
            SCHEMBL19148
        
            SCHEMBL9880011
        
            CHEMBL1897483
        
            AKOS030621531
        
            NCGC00163847-01
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassTrifluoromethylbenzenes
Intermediate Tree NodesNot available
Direct ParentTrifluoromethylbenzenes
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsTrifluoromethylbenzene - Methyl ester - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Alkyl fluoride - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Alkyl halide - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.

Properties

Property NameProperty Value
Molecular Weight408.377
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count9
Rotatable Bond Count8
Complexity607
Monoisotopic Mass408.13
Exact Mass408.13
XLogP4.9
Formal Charge0
Heavy Atom Count29
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9468
Human Intestinal AbsorptionHIA+0.9927
Caco-2 PermeabilityCaco2+0.5304
P-glycoprotein SubstrateNon-substrate0.6388
P-glycoprotein InhibitorInhibitor0.5396
Non-inhibitor0.6559
Renal Organic Cation TransporterNon-inhibitor0.7524
Distribution
Subcellular localizationMitochondria0.8470
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7349
CYP450 2D6 SubstrateNon-substrate0.8082
CYP450 3A4 SubstrateSubstrate0.5536
CYP450 1A2 InhibitorNon-inhibitor0.5179
CYP450 2C9 InhibitorNon-inhibitor0.6064
CYP450 2D6 InhibitorNon-inhibitor0.8952
CYP450 2C19 InhibitorInhibitor0.6046
CYP450 3A4 InhibitorInhibitor0.5000
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5235
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9921
Non-inhibitor0.8742
AMES ToxicityNon AMES toxic0.6381
CarcinogensCarcinogens 0.5117
Fish ToxicityHigh FHMT0.9284
Tetrahymena Pyriformis ToxicityHigh TPT0.9988
Honey Bee ToxicityLow HBT0.5815
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.5501
Carcinogenicity (Three-class)Non-required0.5563
Model Value Unit
Absorption
Aqueous solubility-4.4657LogS
Caco-2 Permeability1.1727LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7694LD50, mol/kg
Fish Toxicity0.2938pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.4248pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
ParsnipJapan0.1ppm
Citrus fruits0110000European Union0.526/06/2018
Garlic (Twistedleaf garlic,)0220010European Union0.01*26/06/2018
Kapok0402040European Union0.01*26/06/2018
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.526/06/2018
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.526/06/2018
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.526/06/2018
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.526/06/2018
Others (2)0110990European Union0.526/06/2018
Tree nuts0120000European Union0.0226/06/2018
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.0226/06/2018
Brazil nuts0120020European Union0.0226/06/2018
Cashew nuts0120030European Union0.0226/06/2018
Chestnuts0120040European Union0.0226/06/2018
Coconuts (Areca nuts/betel nuts,)0120050European Union0.0226/06/2018
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.0226/06/2018
Macadamias0120070European Union0.0226/06/2018
Pecans (Hickory nuts,)0120080European Union0.0226/06/2018
Pistachios0120100European Union0.0226/06/2018
Walnuts0120110European Union0.0226/06/2018

References

TitleJournalDatePubmed ID
Toxicity of the fungicide trifloxystrobin on tadpoles and its effect on fish-tadpole interaction.Chemosphere2012 Jun22386454
Reducing the impact of pesticides on biological control in Australian vineyards: pesticide mortality and fecundity effects on an indicator species, the predatory mite Euseius victoriensis (Acari: Phytoseiidae).J Econ Entomol2010 Dec21309226