Metalaxyl
Structural formula | |||||||||||||||||||
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Structural formula without stereochemistry | |||||||||||||||||||
General | |||||||||||||||||||
Surname | Metalaxyl | ||||||||||||||||||
other names |
( RS ) -Methyl- N - (2,6-dimethylphenyl) - N - (methoxyacetyl) - DL -alaninate ( IUPAC ) |
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Molecular formula | C 15 H 21 NO 4 | ||||||||||||||||||
Brief description |
white solid |
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External identifiers / databases | |||||||||||||||||||
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properties | |||||||||||||||||||
Molar mass | 279.3 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
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density |
1.2 g cm −3 |
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Melting point |
69-73 ° C |
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boiling point |
295.9 ° C |
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solubility |
heavy in water (8.4 g l −1 at 20 ° C) |
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safety instructions | |||||||||||||||||||
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Toxicological data | |||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Metalaxyl is a chemical compound from the group of acetylalanines . Metalaxyl occurs as a racemic mixture of the ( R ) - and the ( S ) - enantiomer . ( R ) -Metalaxyl is the more potent compound (the eutomer ) and is also known as metalaxyl-M or mefenoxam .
history
Metalaxyl was launched in 1979 by Ciba-Geigy (now Syngenta ) and quickly became one of the most widely used fungicides under the brand names Ridomil and Subdue . In the meantime, however, some resistances have developed, such as B. in Phytophthora infestans . The effect is based on the inhibition of RNA synthesis in the ribosomes.
Extraction and presentation
Metalaxyl can be obtained by reacting 2,6-dimethylaniline (2,6-xylidine) with methyl 2-bromopropionate and methoxyacetyl chloride.
Stereochemistry
The metalaxyl racemate, i.e. the 1: 1 mixture of the ( S ) and ( R ) enantiomers , is of practical relevance :
Enantiomers of metalaxyl | |
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CAS number: 69516-34-3 |
CAS number: 70630-17-0 |
Admission
Metalaxyl-M was approved as a fungicidal active ingredient in the European Union in 2002. The racemic mixture metalaxyl was not included in the list of permitted active ingredients in pesticides following a decision by the EU Commission in 2003 . Following a complaint by a manufacturer, the European Court of Justice overturned this decision in 2007. With effect from July 1, 2010, Metalaxyl was also approved for use as a fungicide in the European Union.
In Germany, plant protection products with the active ingredient Metalaxyl are approved and plant protection products with the active ingredient Metalaxyl-M in Germany, Austria and Switzerland.
Individual evidence
- ^ Müfit Bahadir, Harun Parlar, Michael Spiteller: Springer Umweltlexikon . Springer DE, 2000, ISBN 3-642-56998-6 , pp. 757 ( limited preview in Google Book search).
- ↑ a b c d e f g Entry on metalaxyl in the GESTIS substance database of the IFA , accessed on January 21, 2020(JavaScript required) .
- ^ JH Montgomery (ed.): Agrochemicals Desk Reference. Environmental data . Lewis Publishers, Inc., Chelsea, Michigan 1993.
- ↑ Entry on Methyl N- (2,6-dimethylphenyl) -N- (methoxyacetyl) -DL-alaninate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can use the harmonized classification and expand labeling .
- ↑ MEFENOXAM The Active Ingredient in Ridomil Gold
- ↑ Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 904 ( limited preview in Google Book search).
- ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-08-095716-1 , pp. 34 ( limited preview in Google Book search).
- ↑ Directive 2002/64 / EC of the Commission of July 15, 2002 amending Directive 91/414 / EEC of the Council for the inclusion of the active substances Cinidon-ethyl, Cyhalofop-butyl, Famoxadone, Florasulam, Metalaxyl-M and Picolinafen (PDF)
- ↑ Directive 2010/28 / EU of the Commission of April 23, 2010 amending Council Directive 91/414 / EEC to include the active substance metalaxyl (PDF)
- ↑ General Directorate Health and Food Safety of the European Commission: Entry on Metalaxyl in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 29, 2020.
- ↑ General Directorate Health and Food Safety of the European Commission: Entry on Metalaxyl-M in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 29, 2020.