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MCPA information


MCPA
Structural formula of MCPA
Ball-and-stick model of the MCPA molecule
Names
Preferred IUPAC name
(4-Chloro-2-methylphenoxy)acetic acid
Other names
2-(4-Chloro-2-methylphenoxy)acetic acid
4-Chloro-o-tolyloxyacetic acid
MCPA
Identifiers
CAS Number
  • 94-74-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:50099 checkY
ChEMBL
  • ChEMBL394657 checkY
ChemSpider
  • 6935 checkY
ECHA InfoCard 100.002.146 Edit this at Wikidata
KEGG
  • C18528 checkY
PubChem CID
  • 7204
UNII
  • D888C394VO checkY
CompTox Dashboard (EPA)
  • DTXSID4024195 Edit this at Wikidata
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) checkY
    Key: WHKUVVPPKQRRBV-UHFFFAOYSA-N checkY
  • 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−1
Appearance White to light brown solid
Density 1.18-1.21 g/cm3
Melting point 114 to 118 °C (237 to 244 °F; 387 to 391 K)
Solubility in water
825 mg/L (23 °C),[1]
amine salt[which?]: 866 g/L
ester[which?]: 5 mg/L
Hazards
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

MCPA (2-methyl-4-chlorophenoxyacetic acid) is a widely used phenoxy herbicide introduced in 1945. It selectively controls broad-leaf weeds in pasture and cereal crops. The mode of action of MCPA is as an auxin, which are growth hormones that naturally exist in plants.[2][3]

  1. ^ Gimeno, Olga; Plucinski, Pawel; Kolaczkowski, Stan T.; Rivas, Francisco J.; Alvarez, Pedro M. (2003). "Removal of the Herbicide MCPA by Commercial Activated Carbons: Equilibrium, Kinetics, and Reversibility". Industrial & Engineering Chemistry Research. 42 (5): 1076–1086. doi:10.1021/ie020424x.
  2. ^ Reade, J., Cobb, A. H. (2002). Herbicides: Modes of action and metabolism. Weed management handbook. pp. 157–158.{{cite book}}: CS1 maint: multiple names: authors list (link)
  3. ^ Grossmann, K. (2010). "Auxin herbicides: current status of mechanism and mode of action". Pest Management Science. 66 (2): 2033–2043. doi:10.1002/ps.1860. PMID 19823992.

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MCPA

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MCPA (2-methyl-4-chlorophenoxyacetic acid) is a widely used phenoxy herbicide introduced in 1945. It selectively controls broad-leaf weeds in pasture and...

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Methylene cyclopropyl acetic acid

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Methylene cyclopropyl acetic acid (MCPA) is found in lychee seeds and also a toxic metabolite in mammalian digestion after eating hypoglycin, present in...

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Phenoxy herbicide

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selectively kill broad-leaf weeds, leaving the crops relatively unaffected. IAA MCPA 2,4-D 2,4,5-T Introduced in 1946, these herbicides were in widespread use...

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Albania "Management Plan for National Marine Park Karaburun-Sazan" (PDF). mcpa.iwlearn.org. p. 10. The total area of National Park Karaburun-Sazan is 12...

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Jamaican vomiting sickness

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hypoglycin A is metabolized to produce methylenecyclopropylacetic acid (MCPA). MCPA acts to inhibit the beta-oxidation of fatty acids in two ways. First...

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Ackee

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in the body to methylenecyclopropylacetic acid (MCPA), and are toxic with potential lethality. MCPA and hypoglycin A inhibit several enzymes involved...

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Hypoglycin A

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into highly toxic MCPA-CoA. The FAD cofactor necessary for the beta oxidation of fatty acids associates with the alpha carbon of MCPA-CoA creating an irreversible...

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Mecoprop

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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...

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Phenoxyacetic acid

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forms the part-structure of many phenoxy herbicide derivatives including MCPA and 2,4-D. Phenoxyacetic acid is an O-phenyl derivative of glycolic acid...

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Herbicide

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acid mimic the natural auxin indoleacetic acid (IAA). This family includes MCPA, 2,4-D, and 2,4,5-T, picloram, dicamba, clopyralid, and triclopyr. Using...

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Sazan

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April 2017. "Management Plan for National Marine Park Karaburun-Sazan". mcpa.iwlearn.org. p. 10. The total area of National Park Karaburun-Sazan is 12...

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Chloroacetic acid

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etherification with chlorophenols. In this way 2-methyl-4-chlorophenoxyacetic acid (MCPA), 2,4-dichlorophenoxyacetic acid, and 2,4,5-trichlorophenoxyacetic acid (2...

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Astra Lost in Space

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group of students from Caird High School departs to the nearby planet of McPa for their Planetary Camp. Soon after the group arrives on the planet, the...

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Soliva sessilis

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its seeds germinate. Effective herbicides are typically combinations of MCPA and Dicamba, which target broad-leaved plants but not grasses. These chemicals...

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Edgar King

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Edgar Samuel John King CMG DSc FRACP FRACS MCPA FAA, (10 June 1900, Mosgiel, Otago, New Zealand – 31 January 1966, East Melbourne, Victoria, Australia)...

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Cirsium arvense

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by phenoxy compounds (especially MCPA) caused drastic declines in thistle infestation in Sweden in the 1950s. MCPA and clopyralid are approved in some...

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Marathon Petroleum

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Wikimedia Commons has media related to Marathon Petroleum. Official website www.mcpa.org Business data for Marathon Petroleum: Google SEC filings Yahoo!...

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Cresol

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antioxidant Derivatives of o-cresol include: Indo-1, a popular calcium indicator MCPA, (4-chloro-2-methylphenoxy)acetic acid MCPB, 4-(4-chloro-2-methylphenoxy)butanoic...

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Merit Academy

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Merit College Preparatory Academy (MCPA) is a public chartered high school serving grades 7–12 in Springville, Utah, United States, which opened in 2008...

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Chlorophenoxy herbicide

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Chlorophenoxy herbicides are a subclass of phenoxy herbicides which includes: MCPA, 2,4-D, 2,4,5-T and mecoprop. Large amounts have been produced since the...

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Pesticide poisoning

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been used in acute poisonings from chlorophenoxy herbicides (such as 2,4-D, MCPA, 2,4,5-T and mecoprop); however, evidence to support its use is poor. Acute...

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Agent Orange

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herbicidal weapons for use during World War II. These included 2,4-D, 2,4,5-T, MCPA (2-methyl-4-chlorophenoxyacetic acid, 1414B and 1414A, recoded LN-8 and LN-32)...

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Marine protected area

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Diversity defined the broader term of marine and coastal protected area (MCPA): Any defined area within or adjacent to the marine environment, together...

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Auxin

Last Update:

acid, 1-naphthaleneacetic acid derivatives 2,4-D, 2,4-DP 2,4-DB 2,4,5-T MCPA MCPB, mecoprop Some synthetic auxins, such as 2,4-D and 2,4,5-trichlorophenoxyacetic...

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