2-Methyl-4-Chlorophenoxyacetic Acid

Template:Chembox E numberTemplate:Chembox AppearanceTemplate:Chembox DensityTemplate:Chembox MeltingPtTemplate:Chembox SolubilityInWaterTemplate:Chembox Structure

MCPA

File:MCPA structure.png
Names
IUPAC name (4-Chloro-2-methylphenoxy)acetic acid
Other names 4-Chloro-o-tolyloxyacetic acid MCPA
Identifiers
CAS Number	94-74-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:50099 Y
ChEMBL	ChEMBL394657 Y
ChemSpider	6935 Y
ECHA InfoCard
KEGG	C18528 Y
PubChem CID	7204
InChI InChI=1S/C9H9ClO3/c1-6-4-7(10)2-3-8(6)13-5-9(11)12/h2-4H,5H2,1H3,(H,11,12) Y Key: WHKUVVPPKQRRBV-UHFFFAOYSA-N Y InChI=1/C9H9ClO3/c1-6-4-7(10)2-3-8(6)13-5-9(11)12/h2-4H,5H2,1H3,(H,11,12) Key: WHKUVVPPKQRRBV-UHFFFAOYAG
SMILES Cl-C1=CC=C(OCC(=O)O)C(C)=C1
Properties
Chemical formula	C9H9ClO3
Molar mass	200.62 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

MCPA or 2-methyl-4-chlorophenoxyacetic acid is a powerful, selective, widely used phenoxy herbicide. The pure compound is a brown-colored powder.

History

In 1936 investigations began at ICIs Jealott's Hill research centre into the effects of synthetic hormones on plant growth looking specifically for a way to kill weeds without harming crops such as corn.

Synthesis of MCPA was first reported by Synerholme and Zimmerman in 1945 and by Templeman and Foster in 1946. Templeman and Foster were searching for compounds with similar or greater selective activity than 1-naphthaleneacetic acid in inhibiting the growth of weeds while not adversely affecting the growth of cereal grains. They synthesized MCPA from the corresponding phenol by exposing it to chloroacetic acid and dilute base in a straightforward substitution reaction:

2-methyl-4-chlorophenol + ClCH₂CO₂H + base → MCPA + base·HCl

Commercial use

MCPA is used as an herbicide, generally as its salt or esterified forms. Used thus, it controls broadleaf weeds, including thistle and dock, in cereal crops and pasture. It is selective for plants with broad leaves, and this includes most deciduous trees. Clovers are tolerant at moderate application levels. It is currently classified as a restricted use pesticide in the United States. Its toxicity and biodegradation are topics of current research. One formulation is described by its manufacturer as "designed for specific markets that require the safest possible phenoxy product, primarily for use in the Pacific Northwest". Though not extremely toxic, it has recently been determined that MCPA can form complexes with metal ions and thereby increase their bioavailability, though there is also work being done to utilize this ability.

Chemical use

Because it is inexpensive, MCPA is used in various chemical applications. Its carboxylic acid group allows the formation of conjugated complexes with metals (see below). The acid functionality makes MCPA a versatile synthetic intermediate for more complex derivatives.

Brand names

The following commercial products contain MCPA.

• Agritox, Agroxone, Chiptox, Chwastox, Cornox, Methoxone, Rhonox, Spurge Power, Tigrex, Verdone Extra (UK), Weed-Rhap, Weed'n'Feed, Weed-B-Gone, Zero Bindii & Clover Weeder (Aus)