Imazamox

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Structural formula
Imazamox structural formula
Structural formula without stereochemistry
General
Surname Imazamox
other names
  • ( RS ) -5- (methoxymethyl) -2- (4-methyl-5-oxo-4-propan-2-yl-1 H -imidazol-2-yl) pyridine-3-carboxylic acid
  • (±) -5- (methoxymethyl) -2- (4-methyl-5-oxo-4-propan-2-yl-1 H -imidazol-2-yl) pyridine-3-carboxylic acid
Molecular formula C 15 H 19 N 3 O 4
External identifiers / databases
CAS number
  • 114311-32-9 (racemate)
  • 355838-61-8 [( S ) -form]
  • 221298-64-2 [( R ) -form]
EC number 601-305-7
ECHA InfoCard 100.127.347
PubChem 86137
ChemSpider 77711
Wikidata Q17166948
properties
Molar mass 305.33 g mol −1
Physical state

firmly

Melting point

166.3 ° C

solubility
  • in water = 626 g l −1
  • in hexane = 7 mg l −1
  • in toluene = 2.2 g l −1
  • in methanol = 76 g l −1
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
09 - Dangerous for the environment

Caution

H and P phrases H: 410
P: 273-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Imazamox is used as a herbicide in agriculture . BASF products containing this active ingredient are available in Germany. It belongs to the group of imidazolinones.

use

Products with the active ingredient Imazamox are used in arable farming . It is suitable for combating weeds in rapeseed cultivation. Although canola itself is a cruciferous plant , it is used against other cruciferous plants that are weeds. The cultivated rape varieties are equipped with resistance to Imazamox in order not to be attacked themselves. More weeds in oilseed rape and target organisms for the establishment of imazamox are various geraniaceae .

Stereochemistry

Imazamox has a stereocenter and accordingly forms two enantiomers . The racemate is used , i.e. a 1: 1 mixture of the ( S ) and ( R ) form:

Enantiomers of Imazamox
(S) -Enantiomer Imazamox structural formula V1.svg
CAS number: 355838-61-8 		(R) -Enantiomer Imazamox structural formula V1.svg
CAS number: 221298-64-2

effect

Imazamox one of the HRAC Group B, the ALS - inhibitors . It inhibits the enzyme acetolactate synthase, which enzymatically catalyzes chemical reactions within various metabolic pathways . The inhibition has the consequence that the amino acids valine , leucine and isoleucine can no longer be synthesized by the affected tissues. This leads to the death of the plant.

Admission

Imazamox has been approved in the EU since July 1, 2003 . The approval was last extended on November 1, 2017.

Individual evidence

  1. ↑ a b Entry on Imazamox in the GESTIS substance database of the IFA , accessed on January 19, 2018(JavaScript required) .
  2. ↑ a b c d e f Entry on Imazamox in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on January 19, 2018.
  3. ↑ Entry on Imazamox in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 28, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. ↑ Imazamox data sheet at Sigma-Aldrich , accessed on January 21, 2018 ( PDF ).
  5. ↑ List of approved plant protection products from the Federal Office for Consumer Protection and Food Safety , last accessed on January 21, 2018.
  6. ↑ Instructions for use Clearfield®-Vantiga® D. (PDF) BASF, accessed on January 21, 2018 .
  7. ↑ a b Implementing Regulation (EU) No. 540/2011 of the Commission of May 25, 2011 for 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 21, 2018 , P. 13.
  8. ↑ European Food Safety Authority (EFSA): Peer review of the pesticide risk assessment of the active substance imazamox . In: EFSA Journal. April 2016, DOI: 10.2903 / j.efsa.2016.4432 , p. 8.
  9. ↑ Hans-Walter Heldt, Birgit Piechulla: Plant biochemistry . Springer-Verlag Berlin Heidelberg, 2015, DOI: 10.1007 / 978-3-662-44398-9 , pp. 281-283.
  10. ↑ Implementing Regulation (EU) 2017/1531 of the Commission of 7 September 2017 renewing the approval for the active substance Imazamox as a substitution candidate in accordance with Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending the Annex of the Commission Implementing Regulation (EU) No. 540/2011 , accessed on January 21, 2018