Mesotrione

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Structural formula
Structural formula of mesotrione
General
Surname Mesotrione
other names

2 - [(4-methylsulfonyl) -2-nitrobenzoyl] cyclohexane-1,3-dione

Molecular formula C 14 H 13 NO 7 S
Brief description

yellowish solid

External identifiers / databases
CAS number 104206-82-8
EC number 600-533-4
ECHA InfoCard 100.111.661
PubChem 175967
Wikidata Q409390
properties
Molar mass 339.32 g mol −1
Physical state

firmly

density

1.49 g cm −3 (bulk density)

Melting point

165.3 ° C

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 .

Mesotrione is an active ingredient for crop protection and a chemical compound from the group of cyclohexane derivatives .

history

Mesotrione is a herbicide -Wirkstoff from the class of Triketones which on leptospermone from Callistemon citrinus decline. Its herbicidal effect was found in 1977 by a researcher at the Western Research Center of Stauffer Chemical .

Extraction and presentation

Mesotrione can be obtained by reacting 1,3-cyclohexanedione with 2-nitro-4-methylsulfonylbenzoyl chloride.

properties

Mesotrione is a yellowish solid.

use

Mesotrione works by inhibiting 4-hydroxyphenylpyruvate dioxygenase (HPPD), an important enzyme in the biosynthesis of carotenoids . It was brought onto the market in 2001. Nitisinone is a derivative of mesotrione , and sulcotrione is structurally similar .

Admission

The active ingredient mesotrione was approved for use as a herbicide in the European Union in 2003.

In Germany, Austria and Switzerland, plant protection products with this active ingredient are approved. The most important area of ​​application is corn cultivation.

Individual evidence

  1. ↑ a b c Entry on mesotrione in the GESTIS substance database of the IFA , accessed on January 29, 2012(JavaScript required) .
  2. ↑ a b Entry on mesotrione in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.
  3. ↑ Entry on 2- [4- (methylsulfonyl) -2-nitrobenzoyl] -1,3-cyclohexanedione Template: Linktext-Check / Escaped 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 labeling expand .
  4. ↑ Mesotrione data sheet at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
  5. ↑ a b History of mesotrione
  6. ↑ Renaud Beaudegnies, Andrew JF Edmunds, Torquil EM Fraser, Roger G. Hall, Timothy R. Hawkes, Glynn Mitchell, Juergen Schaetzer, Sebastian Wendeborn, Jane Wibley: Herbicidal 4-hydroxyphenylpyruvate dioxygenase inhibitors – A review of the triketone chemistry story from a Syngenta perspective . In: Bioorganic & Medicinal Chemistry . tape 17 , no. June 12 , 2009, p. 4134-4152 , doi : 10.1016 / j.bmc.2009.03.015 ( PDF ).
  7. ↑ Raj B. Durairaj: resorcinol: chemistry, technology, and applications . Springer, Berlin / Heidelberg 2005, ISBN 3-540-25142-1 .
  8. ↑ Josie Annalee Hugie: Understanding the interaction of mesotrione and atrazine in redroot pigweed . University of Illinois at Urbana-Champaign ( p. 4 in Google Book Search).
  9. ↑ Directive 2003/68 / EC of the Commission of July 11, 2003 amending Council Directive 91/414 / EEC to include the active substances trifloxystrobin, carfentrazone-ethyl, mesotrione, fenamidone and isoxaflutole (PDF)
  10. ↑ General Directorate Health and Food Safety of the European Commission: Entry on mesotrione in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.