Methylchlorophenoxypropionic Acid

Basic Info

Common NameMethylchlorophenoxypropionic Acid(F03898)
2D Structure
Description

Mecoprop, or methylchlorophenoxypropionic acid (MCPP), is a common general use herbicide found in many household weed killers and weed-and-feed type lawn fertilizers. It is primarily used to control broadleaf weeds. It is often used in combination with other chemically related herbicides such as 2,4-D, dicamba, and MCPA.The United States Environmental Protection Agency has classified mecoprop as toxicity class III - slightly toxic. Mecoprop is a mixture of two stereoisomers, with the (R)-(+)-enantiomer ('Mecoprop-P', 'Duplosan KV') possessing the herbicidal activity

FRCD IDF03898
CAS Number93-65-2
PubChem CID7153
FormulaC10H11ClO3
IUPAC Name

2-(4-chloro-2-methylphenoxy)propanoic acid

InChI Key

WNTGYJSOUMFZEP-UHFFFAOYSA-N

InChI

InChI=1S/C10H11ClO3/c1-6-5-8(11)3-4-9(6)14-7(2)10(12)13/h3-5,7H,1-2H3,(H,12,13)

Canonical SMILES

CC1=C(C=CC(=C1)Cl)OC(C)C(=O)O

Isomeric SMILES

CC1=C(C=CC(=C1)Cl)OC(C)C(=O)O

Synonyms
        
            2-(4-Chloro-2-methylphenoxy)propanoic acid
        
            MECOPROP
        
            93-65-2
        
            Mecopeop
        
            Compitox
        
            Rankotex
        
            Anicon B
        
            Mechlorprop
        
            Isocarnox
        
            Kilprop
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
Subclass2-phenoxypropionic acids
Intermediate Tree NodesNot available
Direct Parent2-phenoxypropionic acids
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
Substituents2-phenoxypropionic acid - Phenoxyacetate - Phenoxy compound - Phenol ether - Alkyl aryl ether - Toluene - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carboxylic acid derivative - Carboxylic acid - Ether - Monocarboxylic acid or derivatives - Organooxygen compound - Organic oxygen compound - Carbonyl group - Organic oxide - Organochloride - Hydrocarbon derivative - Organohalogen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as 2-phenoxypropionic acids. These are aromatic compounds hat contain a phenol ether attached to the C2-atom of a phenylpropionic acid.

Properties

Property NameProperty Value
Molecular Weight214.645
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity208
Monoisotopic Mass214.04
Exact Mass214.04
XLogP3.1
Formal Charge0
Heavy Atom Count14
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9039
Human Intestinal AbsorptionHIA+0.9907
Caco-2 PermeabilityCaco2+0.7983
P-glycoprotein SubstrateNon-substrate0.7062
P-glycoprotein InhibitorNon-inhibitor0.9443
Non-inhibitor0.9702
Renal Organic Cation TransporterNon-inhibitor0.9178
Distribution
Subcellular localizationMitochondria0.9347
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7808
CYP450 2D6 SubstrateNon-substrate0.8968
CYP450 3A4 SubstrateNon-substrate0.5763
CYP450 1A2 InhibitorNon-inhibitor0.7990
CYP450 2C9 InhibitorNon-inhibitor0.8833
CYP450 2D6 InhibitorNon-inhibitor0.9268
CYP450 2C19 InhibitorNon-inhibitor0.8458
CYP450 3A4 InhibitorNon-inhibitor0.9361
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8493
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9756
Non-inhibitor0.9417
AMES ToxicityNon AMES toxic0.9292
CarcinogensNon-carcinogens0.7736
Fish ToxicityHigh FHMT0.9453
Tetrahymena Pyriformis ToxicityHigh TPT0.9659
Honey Bee ToxicityHigh HBT0.7611
BiodegradationNot ready biodegradable0.8886
Acute Oral ToxicityIII0.8586
Carcinogenicity (Three-class)Non-required0.5206
Model Value Unit
Absorption
Aqueous solubility-2.6504LogS
Caco-2 Permeability1.1632LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4463LD50, mol/kg
Fish Toxicity0.6291pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2796pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
(e) other fruiting vegetables0239000European Union0.05*01/09/2008
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.05*01/09/2008
Citrus fruits0110000European Union0.05*01/09/2008
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.05*01/09/2008
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.05*01/09/2008
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.05*01/09/2008
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.05*01/09/2008
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.05*01/09/2008
Others (2)0110990European Union0.05*01/09/2008
Tree nuts0120000European Union0.05*01/09/2008
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.05*01/09/2008
Brazil nuts0120020European Union0.05*01/09/2008
Cashew nuts0120030European Union0.05*01/09/2008
Chestnuts0120040European Union0.05*01/09/2008
Coconuts (Areca nuts/betel nuts,)0120050European Union0.05*01/09/2008
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.05*01/09/2008
Macadamias0120070European Union0.05*01/09/2008
Pecans (Hickory nuts,)0120080European Union0.05*01/09/2008
Pistachios0120100European Union0.05*01/09/2008
Walnuts0120110European Union0.05*01/09/2008

References

TitleJournalDatePubmed ID
Importance of Toxicokinetics to Assess the Utility of Zebrafish Larvae as Modelfor Psychoactive Drug Screening Using Meta-Chlorophenylpiperazine (mCPP) asExample.Front Pharmacol2018 Apr 2629755353
Evaluating pharmacological models of high and low anxiety in sheep.PeerJ2015 Dec 1426713255
Emerging contaminants (pharmaceuticals, personal care products, a food additiveand pesticides) in waters of Sydney estuary, Australia.Mar Pollut Bull2015 Aug 1526130525
Effects of a herbicide mixture on primary and bacterial productivity in fourprairie wetlands with varying salinities: an enclosure approach.Sci Total Environ2015 Apr 1525644848
Selection of organic process and source indicator substances for theanthropogenically influenced water cycle.Chemosphere2015 Apr25563167
Determination and occurrence of phenoxyacetic acid herbicides and theirtransformation products in groundwater using ultra high performance liquidchromatography coupled to tandem mass spectrometry.Molecules2014 Dec 1025514054
Effects of herbicide mixture on microbial communities in prairie wetlandecosystems: a whole wetland approach.Sci Total Environ2012 Oct 122846761
Evidence for behavioral preference toward environmental concentrations ofurban-use herbicides in a model adult fish.Environ Toxicol Chem2011 Sep21647945
National study of exposure to pesticides among professional applicators: aninvestigation based on urinary biomarkers.J Agric Food Chem2010 Sep 2220799690
Using lysimeters to evaluate the relative mobility and plant uptake of fourherbicides in a rye production system.J Agric Food Chem2009 Mar 1119199601
Adsorption effect on the degradation of carbaryl, mecoprop, and paraquat byanodic fenton treatment in an SWy-2 montmorillonite clay slurry.J Agric Food Chem2008 Nov 1218850712
Effects of a Cannabinoid1 receptor antagonist and Serotonin2C receptor agonistalone and in combination on motivation for palatable food: a dose-additionanalysis study in mice.J Pharmacol Exp Ther2008 May18256173
Effect of different soil textures on leaching potential and degradation ofpesticides in biobeds.J Agric Food Chem2004 Sep 815373405
Anxiety-like state associates with taste to produce conditioned taste aversion.Biol Psychiatry2004 Dec 115576070
A 5-HT2C agonist elicits hyperactivity and oral dyskinesia with hypophagia inrabbits.Physiol Behav2004 Aug15234597
Oral administration of the 5-HT2Creceptor agonist, mCPP, reduces body weight gainin rats over 28 days as a result of maintained hypophagia.Psychopharmacology (Berl)2003 May12690422
Effect of brain serotoninergic stimulation on sodium appetite of euthyroid andhypothyroid rats.Exp Physiol2003 Mar12621530
Herbicide and nutrient transport from an irrigation district into the SouthSaskatchewan River.J Environ Qual2001 Sep-Oct11577889
Development of a solid-phase extraction method for phenoxy acids and bentazone inwater and comparison to a liquid-liquid extraction method.J Agric Food Chem2000 Dec11141255
Influence of molecular structure on sorption of phenoxyalkanoic herbicides onsoil and its particle size fractions.J Agric Food Chem2000 Aug10956177