Zoxamide

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Structural formula
Structural formula
Simplified structural formula without stereochemistry
General
Surname Zoxamide
other names
  • 3,5-dichloro- N - (3-chloro-1-ethyl-1-methyl-2-oxopropyl) -4-methylbenzamide
  • ( RS ) -3,5-dichloro- N - (3-chloro-1-ethyl-1-methyl-2-oxopropyl) - p -toluamide
  • (±) -3,5-dichloro- N - (3-chloro-1-ethyl-1-methyl-2-oxopropyl) - p -toluamide
  • rac -3,5-dichloro- N - (3-chloro-1-ethyl-1-methyl-2-oxopropyl) - p -toluamide
Molecular formula C 14 H 16 Cl 3 NO 2
Brief description

colorless powder

External identifiers / databases
CAS number
  • 156052-68-5 (racemate)
  • 202126-95-2 [( S ) -form]
  • 202126-97-4 [( R ) -form]
EC number 605-037-1
ECHA InfoCard 100.112.164
PubChem 122087
Wikidata Q19312105
properties
Molar mass 336.64 g mol −1
Physical state

firmly

Melting point

159.5-160.5 ° C

solubility

practically insoluble in water (0.68 mg l −1 at 20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 317-410
P: 273-280-305 + 351 + 338-333 + 313-391-501
Toxicological data

> 5000 mg kg −1 ( LD 50ratoral )

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
(S) -Enantiomer Zoxamid structural formula V1.svg
( S ) shape
(R) -Enantiomer Zoxamid structural formula V1.svg
( 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

  1. a b c d e f Entry on zoxamide. In: Römpp Online . Georg Thieme Verlag, accessed on January 4, 2015.
  2. 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) .
  3. 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 .
  4. Zoxamide data sheet from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
  5. 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 ).
  6. 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.
  7. 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
  8. 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.