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Revision as of 17:38, 11 March 2021 editMichael D. Turnbull (talk | contribs)Extended confirmed users13,826 editsm Checked chebi← Previous edit Latest revision as of 23:26, 25 October 2023 edit undoBenjah-bmm27 (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers14,702 edits added a ball-and-stick model of the molecule based on crystallography 
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| ImageFile =Mecoprop.svg | ImageFile =Mecoprop.svg
| ImageSize = | ImageSize =
| ImageFile1 = Mecoprop-racemic-dimer-from-xtal-labelled-3D-balls.png
| IUPACName =(''RS'')-2-(4-Chloro-2-methylphenoxy)propanoic acid | IUPACName =(''RS'')-2-(4-Chloro-2-methylphenoxy)propanoic acid
| OtherNames = | OtherNames =
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| Density = | Density =
| MeltingPtC = 94 to 95 | MeltingPtC = 94 to 95
| MeltingPt_notes = <ref name="GESTIS">{{GESTIS|ZVG=510276|Name=Mecoprop|Date=8 September 2008}}</ref> | MeltingPt_ref = <ref name="GESTIS">{{GESTIS|ZVG=510276|Name=Mecoprop|Date=8 September 2008}}</ref>
| BoilingPt = decomposes <ref name="GESTIS"/> | BoilingPt = decomposes <ref name="GESTIS"/>
| Solubility = 900 mg/L (20 °C)<ref name="GESTIS"/> | Solubility = 900 mg/L (20 °C)<ref name="GESTIS"/>
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}} }}


'''Mecoprop''' (also known as '''methylchlorophenoxypropionic acid''' and '''MCPP''') is a common general use ] found in many household weed killers and "weed-and-feed" type lawn fertilizers.<ref>{{HPD|2529}}</ref> It is primarily used to control broadleaf weeds.<ref name="EXTOXNET"> at EXTOXNET</ref> It is often used in combination with other chemically related herbicides such as ], ], and ]. '''Mecoprop''' (also known as '''methylchlorophenoxypropionic acid''' and '''MCPP''') is a common general use ] found in many household weed killers and "weed-and-feed" type lawn fertilizers.<ref>{{CPID|id=2083|name=2-(2-Methyl-4-chlorophenoxy)propionic acid}}</ref> It is primarily used to control ].<ref name="EXTOXNET"> at EXTOXNET</ref> It is often used in combination with other chemically related herbicides such as ], ], and ], which mimic the plant hormone ] (auxin) and kill most broadleaf weeds by causing uncontrolled growth.


The ] has classified mecoprop as toxicity class III - slightly toxic.<ref name="EXTOXNET"/> The ] has classified mecoprop as toxicity class III - slightly toxic.<ref name="EXTOXNET"/>

Latest revision as of 23:26, 25 October 2023

Mecoprop
Names
IUPAC name (RS)-2-(4-Chloro-2-methylphenoxy)propanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.060 Edit this at Wikidata
EC Number
  • 230-386-8
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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)Key: WNTGYJSOUMFZEP-UHFFFAOYSA-N
  • InChI=1/C10H11ClO3/c1-6-5-8(11)3-4-9(6)14-7(2)10(12)13/h3-5,7H,1-2H3,(H,12,13)Key: WNTGYJSOUMFZEP-UHFFFAOYAN
SMILES
  • CC1=C(C=CC(=C1)Cl)OC(C)C(=O)O
Properties
Chemical formula C10H11ClO3
Molar mass 214.65 g·mol
Appearance Solid
Melting point 94 to 95 °C (201 to 203 °F; 367 to 368 K)
Boiling point decomposes
Solubility in water 900 mg/L (20 °C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Xn, N
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Mecoprop (also known as methylchlorophenoxypropionic acid and 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, which mimic the plant hormone IAA (auxin) and kill most broadleaf weeds by causing uncontrolled growth.

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.

Structures of the two enantiomeric forms (S left, R right) of mecoprop

See also

References

  1. Merck Index, 11th Edition, 5666.
  2. ^ Record of Mecoprop in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 8 September 2008.
  3. 2-(2-Methyl-4-chlorophenoxy)propionic acid in the Consumer Product Information Database
  4. ^ Mecoprop at EXTOXNET
  5. G. Smith; C. H. L. Kennard; A. H. White; P. G. Hodgson (April 1980). "(±)-2-(4-Chloro-2-methylphenoxy)propionic acid (mecoprop)". Acta Crystallogr. B. 36 (4): 992–994. doi:10.1107/S0567740880005134.

External links

Pest control: herbicides
Anilides/anilines
Aromatic acids
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Auxins
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Protox inhibitors
Nitrophenyl ethers
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