Quinclorac

Basic Info

Common NameQuinclorac(F05134)
2D Structure
Description

Quinclorac is a selective herbicide used primarily to control weeds in rice crops, but is also used on other agricultural crops and is found in some household herbicides for lawn use.

FRCD IDF05134
CAS Number84087-01-4
PubChem CID91739
FormulaC10H5Cl2NO2
IUPAC Name

3,7-dichloroquinoline-8-carboxylic acid

InChI Key

FFSSWMQPCJRCRV-UHFFFAOYSA-N

InChI

InChI=1S/C10H5Cl2NO2/c11-6-3-5-1-2-7(12)8(10(14)15)9(5)13-4-6/h1-4H,(H,14,15)

Canonical SMILES

C1=CC(=C(C2=NC=C(C=C21)Cl)C(=O)O)Cl

Isomeric SMILES

C1=CC(=C(C2=NC=C(C=C21)Cl)C(=O)O)Cl

Synonyms
        
            3,7-Dichloroquinoline-8-carboxylic acid
        
            Quinclorac
        
            84087-01-4
        
            Quinchlorac
        
            3,7-Dichloro-8-quinolinecarboxylic acid
        
            Facet
        
            8-Quinolinecarboxylic acid, 3,7-dichloro-
        
            Quinclorac tech
        
            Quinclorac [ISO]
        
            UNII-3J06V625EE
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassQuinolines and derivatives
SubclassQuinoline carboxylic acids
Intermediate Tree NodesNot available
Direct ParentQuinoline carboxylic acids
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsQuinoline-8-carboxylic acid - Haloquinoline - Chloroquinoline - 1-carboxy-2-haloaromatic compound - Aryl chloride - Aryl halide - Benzenoid - Pyridine - Heteroaromatic compound - Vinylogous halide - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Azacycle - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Properties

Property NameProperty Value
Molecular Weight242.055
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Complexity262
Monoisotopic Mass240.97
Exact Mass240.97
XLogP3
Formal Charge0
Heavy Atom Count15
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+0.9654
Human Intestinal AbsorptionHIA+0.9919
Caco-2 PermeabilityCaco2+0.7537
P-glycoprotein SubstrateNon-substrate0.8121
P-glycoprotein InhibitorNon-inhibitor0.9538
Non-inhibitor0.9868
Renal Organic Cation TransporterNon-inhibitor0.8660
Distribution
Subcellular localizationMitochondria0.7023
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7781
CYP450 2D6 SubstrateNon-substrate0.8634
CYP450 3A4 SubstrateNon-substrate0.6630
CYP450 1A2 InhibitorNon-inhibitor0.5290
CYP450 2C9 InhibitorNon-inhibitor0.6867
CYP450 2D6 InhibitorNon-inhibitor0.9054
CYP450 2C19 InhibitorNon-inhibitor0.8415
CYP450 3A4 InhibitorNon-inhibitor0.8882
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9405
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9677
Non-inhibitor0.9351
AMES ToxicityNon AMES toxic0.9600
CarcinogensNon-carcinogens0.8978
Fish ToxicityHigh FHMT0.9357
Tetrahymena Pyriformis ToxicityHigh TPT0.9404
Honey Bee ToxicityLow HBT0.6116
BiodegradationNot ready biodegradable0.9517
Acute Oral ToxicityIII0.7801
Carcinogenicity (Three-class)Non-required0.7252
Model Value Unit
Absorption
Aqueous solubility-4.7721LogS
Caco-2 Permeability1.5442LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0116LD50, mol/kg
Fish Toxicity0.8999pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6157pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
RiceBritain5mg/kg
Other Poultry,EggsJapan0.05ppm
Chicken,EggsJapan0.05ppm
Other Poultry Animals,Edible OffalJapan0.08ppm
Chicken,Edible OffalJapan0.08ppm
Other Poultry Animals,KidneyJapan0.08ppm
Chicken,KidneyJapan0.08ppm
Other Poultry Animals,LiverJapan0.08ppm
Chicken,LiverJapan0.08ppm
Other Poultry Animals,FatJapan0.05ppm
Chicken,FatJapan0.05ppm
Other Poultry Animals,MuscleJapan0.05ppm
Chicken,MuscleJapan0.05ppm
MilkJapan0.1ppm
Other Terrestrial Mammals,Edible OffalJapan0.8ppm
Pig,Edible OffalJapan0.8ppm
Cattle,Edible OffalJapan0.8ppm
Other Terrestrial Mammals,KidneyJapan0.8ppm
Pig,KidneyJapan0.8ppm
Cattle,KidneyJapan0.8ppm

References

TitleJournalDatePubmed ID
Analysis of quinclorac and quinclorac methyl ester in canola from the 2015harvest using QuEChERS with liquid chromatography polarity-switching tandem mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2016Jun27103330
The discovery of Arylex™ active and Rinskor™ active: Two novel auxin herbicides.Bioorg Med Chem2016 Feb 126321602
Occurrence and distribution study of residues from pesticides applied undercontrolled conditions in the field during rice processing.J Agric Food Chem2012 May 922497619
Comparison of extraction solvents and conditions for herbicide residues in milledrice with liquid chromatography-diode array detection analysis (LC-DAD).Food Addit Contam Part A Chem Anal Control Expo Risk Assess2010Feb20013445
Physiological and biochemical characterization of quinclorac resistance in afalse cleavers (Galium spurium L.) biotype.J Agric Food Chem2005 Feb 2315713032

Targets

Target Details

C-C motif chemokine 2

Gene Name:
CCL2
Uniprot ID:
P13500
Molecular Weight:
11024.87 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]