MCPB

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MCPB
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Names
Preferred IUPAC name
4-(4-Chloro-2-methylphenoxy)butanoic acid
Identifiers
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3D model (JSmol)
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  • 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) ☒N
    Key: LLWADFLAOKUBDR-UHFFFAOYSA-N ☒N
  • InChI=1/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)
    Key: LLWADFLAOKUBDR-UHFFFAOYAB
  • CC1=C(C=CC(=C1)Cl)OCCCC(=O)O
Properties
C11H13ClO3
Molar mass 228.67 g/mol
Appearance colourless crystalline solid[1]
Hazards
Lethal dose or concentration (LD, LC):
680 mg/kg (rat, oral)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

MCPB, 2,4-MCPB, 4-(4-chloro-o-tolyloxy)butyric acid (IUPAC), or 4-(4-chloro-2-methylphenoxy)butanoic acid (CAS) is a selective 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.

It is registered in Australia, Canada, Hungary, New Zealand, the UK and the USA. It is not volatile, persistent, or likely to bioconcentrate.[1]

MCPB has to be oxidised into MCPA to have effect; because of this, it is more selective and can be sprayed on more sensitive crops than MCPA.[1]

A variety of methods have been developed for its analysis.[2] In the U.S., the maximum residue permitted on peas is 0.1 parts per million.[3]

It is synthesised by chlorinating o-cresol and coupling it with γ-chlorobutyric acid.[1]

References

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  1. ^ a b c d e Page Module:Citation/CS1/styles.css has no content.Paranjape, Kalyani; Gowariker, Vasant; Krishnamurthy, V.N.; Gowariker, Sudha (2015). The Pesticide Encyclopedia. CABI. ISBN 978-1-78064-014-3.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Wells, M. J. M.; Yu, L. Z. (2000). "Solid-phase extraction of acidic herbicides". Journal of Chromatography A. 885 (1–2): 237–250. doi:10.1016/S0021-9673(00)00206-5. PMID 10941675.
  3. ^ Page Module:Citation/CS1/styles.css has no content."RED FACTS; MCPB". US EPA. Archived from the original on October 6, 2006.
  • MCPB in the Pesticide Properties DataBase (PPDB)

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