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 Edit this at Wikidata
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).

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, 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.[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. ^ a b c d 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. ^ a b 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
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