Mecoprop

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.[3] It is primarily used to control broadleaf weeds.[4] It is often used in combination with other chemically related herbicides such as 2,4-D, dicamba, and MCPA.

Mecoprop[1]
Names
IUPAC name
(RS)-2-(4-Chloro-2-methylphenoxy)propanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.060
EC Number
  • 230-386-8
KEGG
UNII
  • 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) checkY
    Key: WNTGYJSOUMFZEP-UHFFFAOYSA-N checkY
  • 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
  • CC1=C(C=CC(=C1)Cl)OC(C)C(=O)O
Properties
C10H11ClO3
Molar mass 214.65 g·mol−1
Appearance Solid
Melting point 94 to 95 °C (201 to 203 °F; 367 to 368 K)[2]
Boiling point decomposes [2]
900 mg/L (20 °C)[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Xn, N [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The United States Environmental Protection Agency has classified mecoprop as toxicity class III - slightly toxic.[4]

Mecoprop is a mixture of two stereoisomers, with the (R)-(+)-enantiomer ("Mecoprop-P", "Duplosan KV") possessing the herbicidal activity.[5]

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.
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