MCPA
Structural formula | |||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
General | |||||||||||||||||||
Surname | MCPA | ||||||||||||||||||
other names |
|
||||||||||||||||||
Molecular formula | C 9 H 9 ClO 3 | ||||||||||||||||||
Brief description |
yellowish crystalline powder with a phenolic odor |
||||||||||||||||||
External identifiers / databases | |||||||||||||||||||
|
|||||||||||||||||||
properties | |||||||||||||||||||
Molar mass | 200.62 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
||||||||||||||||||
density |
1.56 g cm −3 |
||||||||||||||||||
Melting point |
|
||||||||||||||||||
solubility |
very heavy in water (300 mg l −1 at 25 ° C) |
||||||||||||||||||
safety instructions | |||||||||||||||||||
|
|||||||||||||||||||
Toxicological data | |||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
MCPA, or 2-methyl-4-chlorophenoxyacetic acid, is a powerful, selective, and widely used herbicide .
history
The synthesis of MCPA was published by Synerholme and Zimmerman in 1945 and by Templeman and Foster in 1946 and was the result of finding a more selective substitute for the synthetic auxin 1-naphthylacetic acid .
MCPA is synthesized by a substitution reaction between chloroacetic acid and 4-chloro-2-methylphenol .
use
Since MCPA is an inexpensive substance, it is used as a complex ligand or as a building block for more complex active ingredients.
MCPA is generally used as a salt or as an ester as a herbicide. It is mainly used against broad-leaved weeds such as thistles or dock in agriculture. Although MCPA is not toxic, it has been found to increase the bioavailability of metal ions by forming complexes.
Admission
In a number of EU countries, including Germany and Austria, as well as Switzerland, plant protection products containing this active ingredient are approved.
effect
MCPA is similar to auxin and is a growth substance herbicide that accelerates the growth of weeds so much that the plant dies due to the resulting nutrient deficiency.
Brands
MCPA-containing products are sold under the following brand names:
- Agritox
- Agroxones
- Banvel M
- Chiptox
- Chwastox
- Cornox
- Methoxone
- Rhonox
- Tigrex
- Verdone Extra (GB)
- Weed Rhap
- Weed'n'Feed
- Weed-B-Gone
- Zero Bindii & Clover Weeder (Australia)
- U 46 M fluid
Individual evidence
- ↑ a b c d e f g Entry on (4-chloro-2-methylphenoxy) acetic acid in the GESTIS substance database of the IFA , accessed on February 14, 2017(JavaScript required) .
- ↑ a b Entry on MCPA. In: Römpp Online . Georg Thieme Verlag, accessed on February 22, 2014.
- ↑ Entry on (4-chloro-2-methylphenoxy) acetic acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ^ WG Templeman, WA Sexton: The Differential Effect of Synthetic Plant Growth Substances and other Compounds upon Plant Species. I. Seed Germination and Early Growth Responses to Formula-Naphthylacetic Acid and Compounds of the General Formula arylOCH 2 COOR . In: Proceedings of the Royal Society B: Biological Sciences . tape 133 , no. 872 , August 7, 1946, p. 300-313 , doi : 10.1098 / rspb.1946.0014 .
- ↑ AR Prasad, T. Ramalingam, AB Rao, PV Diwan, PB Sattur: Synthesis and biological evaluation of 3-aryloxyalkyl-6-aryl-7H-s-triazolo [3,4-b] [1,3,4] thiadiazines . In: European Journal of Medicinal Chemistry . 25 1989, pp. 199-201. doi: 10.1016 / 0223-5234 (89) 90116-5 .
- ↑ J. Kobylecka, B. Ptaszynski, R. Rogaczewski, A. Turek: Phenoxyalkanoic acid complexes. Part I. Complexes of lead (II), cadmium (II) and copper (II) with 4-chloro-2-methylphenoxyacetic acid (MCPA) . In: Thermochimica Acta . tape 407 , no. 1-2 , December 2003, pp. 25–31 , doi : 10.1016 / s0040-6031 (03) 00287-9 ( PDF ).
- ↑ General Directorate Health and Food Safety of the European Commission: Entry on MCPA in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 25, 2016.