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Also known as: 2-(4-chloro-2-methylphenoxy)propanoic acid, 93-65-2, Compitox, Mecopeop, 2-(4-chloro-2-methylphenoxy)propionic acid, 7085-19-0
Molecular Formula
C10H11ClO3
Molecular Weight
214.64  g/mol
InChI Key
WNTGYJSOUMFZEP-UHFFFAOYSA-N
FDA UNII
74N8TKR9P8

Mecoprop
1 2D Structure

Mecoprop

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(4-chloro-2-methylphenoxy)propanoic acid
2.1.2 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)
2.1.3 InChI Key
WNTGYJSOUMFZEP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C(C=CC(=C1)Cl)OC(C)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
74N8TKR9P8
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(4-chloro-2-methylphenoxy)propionic Acid

2. 2-methyl-4-chlorophenoxypropionic Acid

3. Mecoprop, (+-)-isomer

4. Mecoprop, (r)-isomer

5. Mecoprop, (s)-isomer

6. Mecoprop, Ammonium Salt

7. Mecoprop, Potassium Salt

8. Mecoprop, Potassium Salt, (+-)-isomer

9. Mecoprop, Sodium Salt

10. Mecoprop, Sodium Salt, (+-)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 2-(4-chloro-2-methylphenoxy)propanoic Acid

2. 93-65-2

3. Compitox

4. Mecopeop

5. 2-(4-chloro-2-methylphenoxy)propionic Acid

6. 7085-19-0

7. Mechlorprop

8. Mecoturf

9. Rankotex

10. Mecprop

11. Morogal

12. Mepro

13. Anicon B

14. Isocarnox

15. Kilprop

16. Liranox

17. Mecopar

18. Mecoper

19. Mecopex

20. Runcatex

21. Proponex-plus

22. Cmpp

23. Iso-cornox

24. Okultin Mp

25. N.b. Mecoprop

26. Vi-par

27. Vi-pex

28. 2m4khp

29. Mecomec

30. 2-mcpp

31. 2-(2-methyl-4-chlorophenoxy)propionic Acid

32. Chipco Turf Herbicide Mcpp

33. Propanoic Acid, 2-(4-chloro-2-methylphenoxy)-

34. 2-(p-chloro-o-tolyloxy)propionic Acid

35. Fbc Cmpp

36. 2m-4cp

37. 2-(2-methyl-4-chlorophenoxy)propanoic Acid

38. 2m 4khp

39. Rd 4593

40. 2-(4-chlorophenoxy-2-methyl)propionic Acid

41. Propionic Acid, 2-(4-chloro-2-methylphenoxy)

42. Propionic Acid, 2-(2-methyl-4-chlorophenoxy)-

43. 2-(4-chloro-2-tolyloxy)propionic Acid

44. 2-(4-chloor-2-methyl-fenoxy)-propionzuur

45. 2-(4-chlor-2-methyl-phenoxy)-propionsaeure

46. 4-chloro-2-methylphenoxy-alpha-propionic Acid

47. Acido 2-(4-cloro-2-metil-fenossi)-propionico

48. Acide 2-(4-chloro-2-methyl-phenoxy)propionique

49. Kwas 4-chloro-2-metylofenoksypropionowy

50. (+)-alpha-(4-chloro-2-methylphenoxy) Propionic Acid

51. 2-(2-methyl-4-chlorphenoxy)-propionsaeure

52. Mls000084910

53. 74n8tkr9p8

54. Chembl272942

55. Chebi:75704

56. Propionic Acid, 2-[(4-chloro-o-tolyl)oxy]-

57. Kyselina 2-(4-chlor-2-methylfenoxy)propionova

58. .alpha.-(2-methyl-4-chlorophenoxy)propionic Acid

59. Celatox Cmpp

60. Nsc-60282

61. Mecoprop 10 Microg/ml In Acetonitrile

62. 2-(4-chloro-o-tolyloxy)propionic Acid

63. Mecoprop 100 Microg/ml In Acetonitrile

64. Smr000019256

65. Sys 67 Mecmin

66. Mecoturf;okultin Mp;2m4khp;nsc 60282

67. U 46 Kv Fluid

68. Dsstox_cid_4194

69. Propionic Acid, 2-((4-chloro-o-tolyl)oxy)-

70. Anicon P

71. 2-(2'-methyl-4'-chlorophenoxy)propionic Acid

72. Dsstox_rid_77323

73. Dsstox_gsid_24194

74. (+/-)-2-(4-chloro-2-methylphenoxy)propionic Acid

75. Caswell No. 559

76. Mecoprop [bsi:iso]

77. Cas-93-65-2

78. Mecoprop [iso]

79. Nsc 60282

80. Ccris 1464

81. (+/-)-mecoprop

82. Hsdb 1738

83. Einecs 202-264-4

84. Einecs 230-386-8

85. Epa Pesticide Chemical Code 031501

86. Brn 2212752

87. Unii-74n8tkr9p8

88. 2-(4-chloro-o-tolyl)oxylpropionic Acid

89. Compitox Plus

90. (rac)-mecoprop

91. Duplosan Cmpp

92. Alpha-(2-methyl-4-chlorophenoxy)propionic Acid

93. Astix Cmpp

94. Kwas 4-chloro-2-metylofenoksypropionowy [polish]

95. 2-(4-chloor-2-methyl-fenoxy)-propionzuur [dutch]

96. 2-(2-methyl-4-chlorphenoxy)-propionsaeure [german]

97. 2-(4-chlor-2-methyl-phenoxy)-propionsaeure [german]

98. Acido 2-(4-cloro-2-metil-fenossi)-propionico [italian]

99. Kyselina 2-(4-chlor-2-methylfenoxy)propionova [czech]

100. Iso-carnox

101. Acide 2-(4-chloro-2-methyl-phenoxy)propionique [french]

102. U 46 Kv-fluid

103. Opera_id_972

104. (+)-2-(4-chloro-2-methylphenoxy)propionic Acid

105. Mecoprop [mi]

106. Duplosan New System Cmpp

107. Ec 230-386-8

108. (+-)-2-((4-chloro-o-tolyl)oxy)propionic Acid

109. Schembl53198

110. (+/-)-2-(4-chloro-2-methylphenoxy)propanoic Acid

111. Wln: Qvy1&or Dg B1

112. Dtxsid9024194

113. Mecoprop, (+/-)-

114. Hms2234f04

115. Hms3371h17

116. Nsc60282

117. Tox21_201667

118. Tox21_303335

119. Bdbm50375464

120. Mfcd00002648

121. Pdsp1_001803

122. Pdsp2_001786

123. Stk208483

124. Akos000120873

125. Akos016890728

126. Rd-4593

127. O-(4-chloro-2-methylphenyl)lactic Acid

128. Ncgc00051613-02

129. Ncgc00051613-03

130. Ncgc00163831-01

131. Ncgc00257155-01

132. Ncgc00259216-01

133. (4-chloro-2-methylphenoxy)propionic Acid

134. Ts-03067

135. 4-chloro-2-methylphenoxy-a-propionic Acid

136. Am20041299

137. Ft-0608602

138. Ft-0670969

139. Ft-0704763

140. Ft-0770555

141. Mecoprop, Pestanal(r), Analytical Standard

142. 2-(4-chloro-o-tolyloxy)propionic Acid, 98%

143. C18742

144. 2-(2'-methyl-4'-chloro-phenoxy)-propionic Acid

145. 2-methyl-4-chlorophenoxy-.alpha.-propionic Acid

146. 4-chloro-2-methylphenoxy-.alpha.-propionic Acid

147. .alpha.-(4-chloro-2-methylphenoxy)propionic Acid

148. 085m190

149. Aj-087/41885651

150. L001008

151. Q149452

152. Sr-01000408149

153. Sr-01000408149-1

154. W-109051

155. (.+/-.)-2-(4-chloro-2-methylphenoxy)propanoic Acid

156. (.+/-.)-2-(4-chloro-2-methylphenoxy)propionic Acid

157. (+)-.alpha.-(4-chloro-2-methylphenoxy) Propionic Acid

158. 3,5-dibromo-2,4-dihydroxybenzoicacidmethylester

159. Propionic Acid, 2-[(4-chloro-o-tolyl)oxy]-, (.+/-.)-

160. Propanoic Acid, 2-(4-chloro-2-methylphenoxy)-, (.+/-.)-

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 214.64 g/mol
Molecular Formula C10H11ClO3
XLogP33.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass214.0396719 g/mol
Monoisotopic Mass214.0396719 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count14
Formal Charge0
Complexity208
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Herbicides

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)


4.2 Absorption, Distribution and Excretion

Male and female Wistar rats with dosed orally with (14)C-Mecoprop-P (radiochemical purity: 99.5%, purity: 98.6%; spec. act.: 138.8 uCi/mg). Five rats/sex were dosed with 5 (Groups A, B, D) or 100 mg/kg (Groups C and E). The rats in Group B received 14 doses of unlabeled Mecoprop-P (purity: 99.8%) at 5 mg/kg/day prior to being dosed with the radiolabeled material. In addition,12 rats/sex were dosed with 5 mg/kg (Group F). In Groups A, B and C, urine and feces were collected for 7 days. Expired air was collected from two males in Group C. In Groups D and E, blood samples were collected for 7 days. In Group F, four animals/sex/timepoint were euthanized at 0.5, 3 and 6 hours after dosing. Absorption of the administered dose ranged from 82.92 to 100.47% with the absorption minimally reduced in the repeated dosing regimen and at the higher dosing level (males: A. 100.47%, B. 94.58%, C. 92.34%; females: A. 94.62%, B. 92.07%, C. 82.92%). Excretion was predominantly via the urine with the percentage of the total dose recovered in the urine and cage wash ranging from 79.74 to 100.06%. In Group A, 95.29 and 92.29% of the administered dose was collected in the urine and the cage wash within the first 24 hours for males and females, respectively. Repeated dosing reduced the amount collected in the urine and the cage wash during the first 24 hours to 88.97 and 86.46% for males and females, respectively. Likewise, at the 100 mg/kg dosing level, the percentage collected in the urine and the cage wash during the first 24 hours was reduced to 61.18 and 56.78% for males and females, respectively. The total radiolabel recovered in the feces ranged from 3.56 to 12.52% of the administered dose. No radiolabeled material was recovered in the expired air due to the positioning of the label on the phenyl ring. Radiolabel in the tissues and organs 7 days after dosing was predominantly in the fat followed by the skin, adrenals, kidneys and liver. Maximal levels of radioactivity were recovered from the various tissues and organs assayed within 3 hours of dosing (Group F). In the plasma pharmacokinetic analysis, Tmax values were 1.8 and 2.7 hours for males and females, respectively in Group D and 4.2 hours in Group E. /The half-life/ for elimination was 6.35 and 4.23 hours in Group D and 7.89 and 7.79 hours in Group E for males and females, respectively. ... /Mecoprop-p/

California Environmental Protection Agency/Department of Pesticide Regulation; Summary of Toxicology Data, MCPP, Chemical Code Nos. 000374, 5333 p.9-10 (September 15, 1999). Available from, as of October 25, 2015: https://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm


Groups of 5 male Wistar rats were dosed orally with 5 mg/kg of either (14)C-Mecoprop-P-EHE (radiochemical purity: 99.6%, spec. act.: 145.37 uCi/mg) (Groups A and C) or (14)C-Mecoprop-P-DMA /(dimethylamine salt)/ (radiochemical purity (based on the acid): 99.8%, spec. act.: 114.79 uCi/mg) (Groups B and D). In Groups A and B (plasma pharmacokinetic study), blood samples were collected for 7 days. In Groups C and D, urine and feces were collected for 7 days. Expired air was collected for 48 hours. In the plasma pharmacokinetic analysis, Tmax values were 3.6 and 2 hr for Groups A and B, respectively. The half-life for elimination was 8.36 and 6.61 hours for Groups A and B, respectively. Absorption of the administered dose was at least 83.26 and 97.11% for Groups C and D, respectively (the total residual radiolabel in the tissues was not determined). Excretion was predominantly via the urine with the percentage of the total dose recovered in the urine 83.26 and 97.11%. In Groups C and D, respectively, 79.73 and 93.52% of the administered dose (calculated by the reviewer) was collected in the urine and the cage wash within the first 24 hours. The total radiolabel recovered in the feces was 3.29 and 4.68% of the administered dose for Groups C and D, respectively. No radiolabeled material was recovered in the expired air due to the positioning of the label on the phenyl ring. Radiolabel in the tissues and organs 7 days after dosing was largely limited to the skin and fat. The only metabolite identified in the study was hydroxymethyl-Mecoprop-P. Overall, unaltered test material and the hydroxylated metabolite constituted 96% of the recovered radiolabel in the first 48 hours after dosing. The parent material constituted 72.91 and 70.68% and the metabolite was 23.13 and 25.26% of the administered dose for Groups C and D, respectively.

California Environmental Protection Agency/Department of Pesticide Regulation; Summary of Toxicology Data, MCPP, Chemical Code Nos. 000374, 5333 p.8-9 (September 15, 1999). Available from, as of October 25, 2015: https://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm


4.3 Metabolism/Metabolites

MCPP-p-DMAS (14)C-MCPP-p DMAS was incubated in vitro with rat plasma, stomach content, gastro-intestinal tract (GIT) or postmitochondrial liver fraction (S9) for 30 minutes. All incubated extracts were subjected to HPLC analysis. Results indicated that all of the administered (14)C-MCPP-p DMAS in plasma, stomach contents, gastro-intestinal tract and liver (S9) was present as the ionized form of (14)C-MCPP-p.

USEPA, Office of Prevention, Pesticides, and Toxic Substances; Revised HED Human Health Risk Assessment for Mecoprop (93-65-2) p.16 (July 2007). EPA Docket No.: EPA-HQ-OPP-2006-0943-0004. Available from, as of October 25, 2017: https://www.regulations.gov/


Male and female Wistar rats with dosed orally with (14)C-Mecoprop-P (radiochemical purity: 99.5%, purity: 98.6%; spec. act.: 138.8 uCi/mg). Five rats/sex were dosed with 5 (Groups A, B, D) or 100 mg/kg (Groups C and E). The rats in Group B received 14 doses of unlabeled Mecoprop-P (purity: 99.8%) at 5 mg/kg/day prior to being dosed with the radiolabeled material. In addition,12 rats/sex were dosed with 5 mg/kg (Group F). ... The only metabolite identified in the study was hydroxymethyl-Mecoprop-P. A greater percentage of this metabolite was recovered in the urine of the males. Overall, unaltered test material and the hydroxylated metabolite constituted 92.29 to 95.34% of the recovered radiolabel in the urine in the first 48 hours after dosing. For the males, the parent material was 52.17 to 67.08% and the metabolite was 28.26 to 41.39% of the administered dose. For the females these values ranged from 84.31 to 90.03% for the parent compound and 5.16 to 10.25% for the metabolite. /Mecoprop-p/

California Environmental Protection Agency/Department of Pesticide Regulation; Summary of Toxicology Data, MCPP, Chemical Code Nos. 000374, 5333 p.9 (September 15, 1999). Available from, as of October 25, 2015: https://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm


The dissociation of Mecoprop-p-DMA salt into Mecoprop-P acid and dimethyl amine was examined in various in vitro biological test systems. (14)C-Mecoprop-p-DMA was formed by mixing (14)C-Mecoprop-p acid (radiochemical purity: 99.5%, chemical purity: 98.6%, specific activity: 138.92 uCi/mg) with a dimethylamine solution. The test material was incubated with plasma (I), stomach contents (II), the gastrointestinal tract (III) and liver S9 fraction (IV) derived from male Wistar rats. The concentrations of the test material in the incubations were 0.1 (I), 5 (II), 0.35 (III) and 0.1 (IV) mg/mL. The samples were incubated for 30 minutes at 37o C. Study results indicated that the test material had largely dissociated into Mecoprop-P acid and DMA. It was not apparent from these results whether the dissociation may have been wholly or partially mediated enzymatically.

California Environmental Protection Agency/Department of Pesticide Regulation; Summary of Toxicology Data, MCPP, Chemical Code Nos. 000374, 5333 p.9 (September 15, 1999). Available from, as of October 25, 2015: https://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm


In ...plants, degradation of the side-chain to 2-methyl-4-chlorophenol, ring hydroxylation and ring opening.

Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. Old Woking, Surrey, United Kingdom: Royal Society of Chemistry/Unwin Brothers Ltd., 1983., p. A255/oct 83


4.4 Biological Half-Life

Groups of 5 male Wistar rats were dosed orally with 5 mg/kg of either (14)C-Mecoprop-P-EHE (radiochemical purity: 99.6%, spec. act.: 145.37 uCi/mg) (Groups A and C) or (14)C-Mecoprop-P-DMA (radiochemical purity (based on the acid): 99.8%, spec. act.: 114.79 uCi/mg) (Groups B and D). ... The half-life for elimination was 8.36 and 6.61 hours for Groups A and B, respectively. ...

California Environmental Protection Agency/Department of Pesticide Regulation; Summary of Toxicology Data, MCPP, Chemical Code Nos. 000374, 5333 p.8 (September 15, 1999). Available from, as of October 25, 2015: https://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm


/In/ two cases of serious intoxication with phenoxy herbicides (MCPP) ... The plasma half-life was about 17 hr. MCPP plasma elimination probably follows first-order kinetics.

PMID:3391629 Meulenbelt J et al; Hum Toxicol 7 (3): 289-92 (1988)


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Mecoprop manufacturers, exporters & distributors 1

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API | Excipient name

Mecoprop

Synonyms

2-(4-chloro-2-methylphenoxy)propanoic acid, 93-65-2, Compitox, Mecopeop, 2-(4-chloro-2-methylphenoxy)propionic acid, 7085-19-0

Cas Number

93-65-2

Unique Ingredient Identifier (UNII)

74N8TKR9P8

Mecoprop Manufacturers

A Mecoprop manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Mecoprop, including repackagers and relabelers. The FDA regulates Mecoprop manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Mecoprop API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Mecoprop Suppliers

A Mecoprop supplier is an individual or a company that provides Mecoprop active pharmaceutical ingredient (API) or Mecoprop finished formulations upon request. The Mecoprop suppliers may include Mecoprop API manufacturers, exporters, distributors and traders.

Mecoprop GMP

Mecoprop Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Mecoprop GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Mecoprop GMP manufacturer or Mecoprop GMP API supplier for your needs.

Mecoprop CoA

A Mecoprop CoA (Certificate of Analysis) is a formal document that attests to Mecoprop's compliance with Mecoprop specifications and serves as a tool for batch-level quality control.

Mecoprop CoA mostly includes findings from lab analyses of a specific batch. For each Mecoprop CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Mecoprop may be tested according to a variety of international standards, such as European Pharmacopoeia (Mecoprop EP), Mecoprop JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Mecoprop USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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