Zoxamide
Structural formula | ||||||||||||||||
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Simplified structural formula without stereochemistry | ||||||||||||||||
General | ||||||||||||||||
Surname | Zoxamide | |||||||||||||||
other names |
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Molecular formula | C 14 H 16 Cl 3 NO 2 | |||||||||||||||
Brief description |
colorless powder |
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External identifiers / databases | ||||||||||||||||
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properties | ||||||||||||||||
Molar mass | 336.64 g mol −1 | |||||||||||||||
Physical state |
firmly |
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Melting point |
159.5-160.5 ° C |
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solubility |
practically insoluble in water (0.68 mg 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 . |
Zoxamid is a chemical compound from the group of benzamides and a fungicide introduced by Rohm & Haas (now Dow AgroSciences ) as a pesticide .
use
Zoxamid is a protective fungicide which, due to its lipophilicity, creates an active ingredient depot in the leaf. This gives it a high level of rain resistance.
Zoxamid is used against Oomycete diseases in potato, vegetable and viticulture such as Phytophthora , Plasmopara and Pseudoperonospora .
The active ingredient binds covalently to the β-tubulin of the spindle apparatus and thus inhibits mitosis.
Stereochemistry
The drug molecule contains a stereogenic center, hence there are two stereoisomers:
- ( R ) -3,5-dichloro- N - (3-chloro-1-ethyl-1-methyl-2-oxopropyl) -4-methylbenzamide and
- ( S ) -3,5-dichloro- N - (3-chloro-1-ethyl-1-methyl-2-oxopropyl) -4-methylbenzamide.
Zoxamid is used as a 1: 1 mixture ( racemate ) of these enantiomers .
Enantiomers of zoxamide | |
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( S ) shape |
( R ) shape |
Admission
In Germany, Austria and Switzerland, as well as many other EU countries, plant protection products with zoxamide as an active ingredient are approved.
Individual evidence
- ↑ a b c d e f Entry on zoxamide. In: Römpp Online . Georg Thieme Verlag, accessed on January 4, 2015.
- ↑ Entry on (RS) -3,5-dichloro-N- (3-chloro-1-ethyl-1-methyl-2-oxopropyl) -p-toluamide in the GESTIS substance database of the IFA , accessed on February 8, 2018(JavaScript required) .
- ↑ Entry on (RS) -3,5-dichloro-N- (3-chloro-1-ethyl-1-methyl-2-oxopropyl) -p-toluamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ Zoxamide data sheet from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
- ↑ Jeffrey S. Miller, Nora Olsen, Lynn Woodell, Lyndon D. Porter, Shane Clayson: Post-harvest applications of zoxamide and phosphite for control of potato tuber rots caused by oomycetes at harvest . In: American Journal of Potato Research . tape 83 , no. 3 , May 2006, pp. 269-278 , doi : 10.1007 / BF02872163 ( PDF ).
- ↑ Elim M. Ulrich, Candice M. Morrison, Michael M. Goldsmith, William T. Foremann: Chiral Pesticides: Identification, Description, and Environmental Implications . In: Reviews of Environmental Contaminations and Toxicology. Springer 2012, Boston, Volume 217, pp. 1–74, DOI: 10.1007 / 978-1-4014-2329-4_1 , see p. 12.
- ↑ Implementing Regulation (EU) No. 540/2011 of the Commission of May 25, 2011 on the implementation of Regulation (EC) No. 1107/2009 of the European Parliament and of the Council with regard to the list of approved active substances , accessed on January 28, 2018 , p. 25th
- ↑ Directorate-General for Health and Food Safety of the European Commission: Entry on zoxamide in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 14, 2016.