Fluridone

Basic Info

Common NameFluridone(F05944)
2D Structure
FRCD IDF05944
CAS Number59756-60-4
PubChem CID43079
FormulaC19H14F3NO
IUPAC Name

1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]pyridin-4-one

InChI Key

YWBVHLJPRPCRSD-UHFFFAOYSA-N

InChI

InChI=1S/C19H14F3NO/c1-23-11-16(13-6-3-2-4-7-13)18(24)17(12-23)14-8-5-9-15(10-14)19(20,21)22/h2-12H,1H3

Canonical SMILES

CN1C=C(C(=O)C(=C1)C2=CC(=CC=C2)C(F)(F)F)C3=CC=CC=C3

Isomeric SMILES

CN1C=C(C(=O)C(=C1)C2=CC(=CC=C2)C(F)(F)F)C3=CC=CC=C3

Synonyms
        
            Caswell No. 130C
        
            FLURIDONE
        
            59756-60-4
        
            Brake
        
            Sonar
        
            Pride
        
            Fluridon
        
            UNII-3L0JQA61JX
        
            EL 171
        
            EL-171
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassPyridines and derivatives
SubclassPhenylpyridines
Intermediate Tree NodesNot available
Direct ParentPhenylpyridines
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
Substituents3-phenylpyridine - Trifluoromethylbenzene - Dihydropyridine - Monocyclic benzene moiety - Hydropyridine - Benzenoid - Heteroaromatic compound - Vinylogous amide - Cyclic ketone - Azacycle - Hydrocarbon derivative - Alkyl fluoride - Organic oxide - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Alkyl halide - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.

Properties

Property NameProperty Value
Molecular Weight329.322
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Complexity543
Monoisotopic Mass329.103
Exact Mass329.103
XLogP3.2
Formal Charge0
Heavy Atom Count24
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9853
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7482
P-glycoprotein SubstrateNon-substrate0.7580
P-glycoprotein InhibitorNon-inhibitor0.6662
Non-inhibitor0.7206
Renal Organic Cation TransporterNon-inhibitor0.6912
Distribution
Subcellular localizationMitochondria0.8906
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7470
CYP450 2D6 SubstrateNon-substrate0.7498
CYP450 3A4 SubstrateNon-substrate0.5000
CYP450 1A2 InhibitorInhibitor0.7932
CYP450 2C9 InhibitorNon-inhibitor0.5580
CYP450 2D6 InhibitorNon-inhibitor0.9015
CYP450 2C19 InhibitorNon-inhibitor0.5377
CYP450 3A4 InhibitorNon-inhibitor0.6396
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6943
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9132
Inhibitor0.6030
AMES ToxicityNon AMES toxic0.7839
CarcinogensNon-carcinogens0.9015
Fish ToxicityHigh FHMT0.9214
Tetrahymena Pyriformis ToxicityHigh TPT0.9830
Honey Bee ToxicityLow HBT0.7123
BiodegradationNot ready biodegradable0.9824
Acute Oral ToxicityIV0.6156
Carcinogenicity (Three-class)Non-required0.5155
Model Value Unit
Absorption
Aqueous solubility-4.3775LogS
Caco-2 Permeability1.5185LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5489LD50, mol/kg
Fish Toxicity0.9094pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.7708pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
CrustaceansJapan0.5ppm
Other FishJapan0.5ppm
PerciformesJapan0.5ppm
AnguilliformesJapan0.5ppm
SalmoniformesJapan0.5ppm
Other Poultry,EggsJapan0.05ppm
Chicken,EggsJapan0.05ppm
Other Poultry Animals,Edible OffalJapan0.05ppm
Chicken,Edible OffalJapan0.05ppm
Other Poultry Animals,KidneyJapan0.01ppm
Chicken,KidneyJapan0.01ppm
Other Poultry Animals,LiverJapan0.01ppm
Chicken,LiverJapan0.01ppm
Other Poultry Animals,FatJapan0.05ppm
Chicken,FatJapan0.05ppm
Other Poultry Animals,MuscleJapan0.05ppm
Chicken,MuscleJapan0.05ppm
MilkJapan0.05ppm
Pig,Edible OffalJapan0.05ppm
Cattle,Edible OffalJapan0.05ppm

References

TitleJournalDatePubmed ID
Omethoate treatment mitigates high salt stress inhibited maize seed germination.Pestic Biochem Physiol2018 Jan29463412
Transcriptome analysis of Phelipanche aegyptiaca seed germination mechanismsstimulated by fluridone, TIS108, and GR24.PLoS One2017 Nov 329099877
Two MYB-related transcription factors play opposite roles in sugar signaling inArabidopsis.Plant Mol Biol2017 Feb27866313
Can heavy metal pollution defend seed germination against heat stress? Effect of heavy metals (Cu(2+), Cd(2+) and Hg(2+)) on maize seed germination under hightemperature.Environ Pollut2016 Sep27239687
A WD40 protein, AtGHS40, negatively modulates abscisic acid degrading andsignaling genes during seedling growth under high glucose conditions.J Plant Res2016 Nov27443795
[Effects of fluridone, gibberellin acid and germination temperature ondormancy-breaking for Epimedium wushanense].Zhongguo Zhong Yao Za Zhi2016 Jul28905597
Karrikins delay soybean seed germination by mediating abscisic acid andgibberellin biogenesis under shaded conditions.Sci Rep2016 Feb 2326902640
The Arabidopsis MYB96 transcription factor plays a role in seed dormancy.Plant Mol Biol2015 Mar25616734
A potential role for endogenous microflora in dormancy release, cytokininmetabolism and the response to fluridone in Lolium rigidum seeds.Ann Bot2015 Feb25471097
Light Inhibition of Shoot Regeneration Is Regulated by Endogenous Abscisic AcidLevel in Calli Derived from Immature Barley Embryos.PLoS One2015 Dec 1526670930
Fluridone: a combination germination stimulant and herbicide for problem fields?Pest Manag Sci2014 Sep24408127
AtRH57, a DEAD-box RNA helicase, is involved in feedback inhibition ofglucose-mediated abscisic acid accumulation during seedling development andadditively affects pre-ribosomal RNA processing with high glucose.Plant J2014 Jan24176057
Nitric oxide is involved in light-specific responses of tomato during germinationunder normal and osmotic stress conditions.Ann Bot2012 Sep22782244
Carotenoid inhibitors reduce strigolactone production and Striga hermonthicainfection in rice.Arch Biochem Biophys2010 Dec 120732294
ABA, GA(3), and nitrate may control seed germination of Crithmum maritimum(Apiaceae) under saline conditions.C R Biol2009 Aug19632653
Genetic variation for lettuce seed thermoinhibition is associated withtemperature-sensitive expression of abscisic Acid, gibberellin, and ethylenebiosynthesis, metabolism, and response genes.Plant Physiol2008 Oct18753282
[Study on conditions of seed germination of Cistanche].Zhongguo Zhong Yao Za Zhi2007 Sep18051886
Expression of PsGRP1, a novel glycine rich protein gene of Pisum sativum, isinduced in developing fruit and seed and by ABA in pistil and root.Planta2006 May16328544
Characterization of a higher plant herbicide-resistant phytoene desaturase andits use as a selectable marker.Plant Biotechnol J2006 Mar17177802
Post-anthesis development of inferior and superior spikelets in rice in relation to abscisic acid and ethylene.J Exp Bot200616330527