4-(4-Chloro-2-Methylphenoxy)Butanoic Acid

Basic Info

Common Name4-(4-Chloro-2-Methylphenoxy)Butanoic Acid(F03897)
2D Structure
Description

4-(4-Chloro-2-methylphenoxy)butanoic acid (MCPB, 2,4-MCPB) is a phenoxybutyric herbicide. In the United States it is registered for use on pea crops before flowering, for post-emergence control of broadleaf annual and perennial weeds including Canadian thistle, buttercup, mustard, purslane, ragweed, common lambsquarters, pigweed, smartweed, sowthistle, and morning glory. It has low to moderate acute toxicity, with kidney and liver effects as the main hazard concerns.

FRCD IDF03897
CAS Number94-81-5
PubChem CID7207
FormulaC11H13ClO3
IUPAC Name

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

InChI Key

LLWADFLAOKUBDR-UHFFFAOYSA-N

InChI

InChI=1S/C11H13ClO3/c1-8-7-9(12)4-5-10(8)15-6-2-3-11(13)14/h4-5,7H,2-3,6H2,1H3,(H,13,14)

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            4-(4-Chloro-2-methylphenoxy)butanoic acid
        
            MCPB
        
            94-81-5
        
            Trifolex
        
            Legumex
        
            Thitrol
        
            Bexone
        
            Trotox
        
            MCP-butyric
        
            4MCPB
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassPhenol ethers
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentPhenol ethers
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenoxy compound - Phenol ether - Alkyl aryl ether - Chlorobenzene - Halobenzene - Toluene - Aryl chloride - Monocyclic benzene moiety - Aryl halide - Monocarboxylic acid or derivatives - Ether - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Organochloride - Organohalogen compound - Carbonyl group - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Properties

Property NameProperty Value
Molecular Weight228.672
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Complexity208
Monoisotopic Mass228.055
Exact Mass228.055
XLogP3.6
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+0.8967
Human Intestinal AbsorptionHIA+0.9777
Caco-2 PermeabilityCaco2+0.6658
P-glycoprotein SubstrateNon-substrate0.5934
P-glycoprotein InhibitorNon-inhibitor0.9011
Non-inhibitor0.9451
Renal Organic Cation TransporterNon-inhibitor0.8225
Distribution
Subcellular localizationMitochondria0.9568
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7358
CYP450 2D6 SubstrateNon-substrate0.8531
CYP450 3A4 SubstrateSubstrate0.5402
CYP450 1A2 InhibitorNon-inhibitor0.6779
CYP450 2C9 InhibitorNon-inhibitor0.7056
CYP450 2D6 InhibitorNon-inhibitor0.9481
CYP450 2C19 InhibitorNon-inhibitor0.9000
CYP450 3A4 InhibitorNon-inhibitor0.9456
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7614
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8731
Non-inhibitor0.8137
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.8897
Fish ToxicityHigh FHMT0.7938
Tetrahymena Pyriformis ToxicityHigh TPT0.9990
Honey Bee ToxicityHigh HBT0.6178
BiodegradationNot ready biodegradable0.5466
Acute Oral ToxicityIII0.8765
Carcinogenicity (Three-class)Non-required0.6587
Model Value Unit
Absorption
Aqueous solubility-3.4564LogS
Caco-2 Permeability1.1966LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4954LD50, mol/kg
Fish Toxicity0.9019pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5793pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
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 Union0.05*05/06/2014
Cassava roots/manioc (Blue taros/blue tannias, Canna, Chayotes/christophines roots, Dasheen taros, Eddoe taros, Konjac roots, Tannias/arrowleaf elephant ears/tajer,)0212010European Union0.05*05/06/2014
Horseradishes (Dandelion roots, Gentiana roots, East Indian galangal/aromatic ginger/sand galangal, Fingerroot, Galangal roots, Galangal roots, Galangal roots, Galangal roots, Ginger roots, Greater...0213040European Union0.05*05/06/2014
Chinese cabbages/pe-tsai (Chinese flat cabbages/tatsoi/tai goo choi, Indian mustards/mustard greens, Komatsuna/mustard spinaches, Mizuna (4), Pak-choi/paksoi, Turnip greens/turnip tops (5), Seakale,)0243010European Union0.05*05/06/2014
Kales (Borecoles/collards greens/curly kales, Cow cabbages/stem kales, Cow cabbages/Jersey kales, Kohlrabies leaves (6), Rape kales/Siberian kales, Portuguese kales/tronchuda kales/Portuguese cabba...0243020European Union0.05*05/06/2014
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 Union0.05*05/06/2014
Beans (without pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap bean...0260020European Union0.105/06/2014
Common millet/proso millet (Black fonio, Canary grass, Finger millet/African millet/koracan, Foxtail millet, Job's tears, Little millet, Pearl millet, Teff/tef, White fonio,)0500040European Union0.05*05/06/2014
Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei...0631030European Union0.1*05/06/2014
Apples (Crab apples/wild apples, Tejocotes,)0130010European Union0.05*05/06/2014
Quinces (Chinese quinces, Japanese quinces,)0130030European Union0.05*05/06/2014
Medlars0130040European Union0.05*05/06/2014
Loquats/Japanese medlars0130050European Union0.05*05/06/2014
Others (2)0130990European Union0.05*05/06/2014
Stone fruits0140000European Union0.05*05/06/2014
Apricots (Japanese apricots/Umes, Nectacots,)0140010European Union0.05*05/06/2014
Cherries (sweet) (Black cherries, Capulins, Chokecherries, Cornelian cherries/European corniols, Nanking cherries, Sour cherries/morello cherries,)0140020European Union0.05*05/06/2014
Peaches (Flat peaches/saturn peaches/paraguayas, Nectarines, Other hybrids of Persica vulgaris; syn: Prunus persica, not elsewhere mentioned,)0140030European Union0.05*05/06/2014
Others (2)0140990European Union0.05*05/06/2014
Berries and small fruits0150000European Union0.05*05/06/2014