Chlorotoluron

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Structural formula
Structural formula of chlorotoluron
General
Surname Chlorotoluron
other names
  • 3- (3-chloro-4-methylphenyl) -1,1-dimethylurea
  • 3- (3-chloro- p -tolyl) -1,1-dimethylurea
  • CTU
  • Dicuran
Molecular formula C 10 H 13 ClN 2 O
Brief description

white crystalline powder

External identifiers / databases
CAS number 15545-48-9
EC number 239-592-2
ECHA InfoCard 100.035.978
PubChem 27375
Wikidata Q411273
properties
Molar mass 212.68 g mol −1
Physical state

firmly

density

1.4 g cm −3

Melting point

148.1 ° C

Vapor pressure

0.005 mPa (25 ° C)

solubility

practically insoluble in water: 0.074 g l −1 (20 ° C)

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

Caution

H and P phrases H: 351-361d-410
P: 273-281-501
Toxicological data

5800 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlortoluron is a chemical compound from the group of phenylureas . It is in the form of a white to yellowish powder.

Extraction and presentation

Chlortoluron can be prepared starting from toluene . This is only to p -Nitrotoluol nitrided (PNT) and then 2-chloro-4-nitrotoluene (2C4NT) chlorinated which to 2-chloro-4-aminotoluene is hydrogenated (2C4AT). The 2-chloro-4-aminotoluene then reacts with phosgene to form chloromethylphenyl isocyanate (CMPI), which reacts with dimethylamine to form chlorotoluron.

use

Chlortoluron was used as a pesticide (urea herbicide) in winter wheat and winter barley, among other things. The mechanism of action after uptake via the roots is based on the inhibition of photosynthesis on photosystem II .

Occurrence in drinking water

In the period 2001–2002, the Dutch waterworks interrupted the extraction of Rhine water for drinking water several times due to excessive concentrations of the herbicides isoproturon and chlorotoluron.

Admission

From July 1, 2001 to 2008, the use of chlorotoluron was banned in Germany. In the Netherlands, approval ended on May 1, 2000; Since May 1, 2002, there has been a ban on use there. Chlortoluron is approved in Belgium, France and Luxembourg.

Preparations containing chlorotoluron are currently approved in many EU countries, as well as in Germany, Austria and Switzerland.

safety instructions

Chlortoluron is suspected of having a carcinogenic effect.

Individual evidence

  1. ↑ a b International Chemical Safety Card (ICSC) for chlorotoluron at the National Institute for Occupational Safety and Health (NIOSH), accessed on December 26, 2017.
  2. ↑ a b c Entry on 3- (3-chloro-4-methylphenyl) -1,1-dimethylurea in the GESTIS substance database of the IFA , accessed on February 21, 2017(JavaScript required) .
  3. ↑ a b Entry on Chlortoluron in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on May 4, 2014.
  4. ↑ Entry on Chlorotoluron in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. ↑ Data chlorotoluron at Sigma-Aldrich retrieved on November 7, 2016 ( PDF ).
  6. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 220 ( limited preview in Google Book search).
  7. ↑ IKSR CIPR ICBR ICPR: 135th synthesis report on isoproturon and chlorotoluron. Retrieved June 6, 2019 .
  8. ↑ Directive 2005/53 / EC (PDF) of the Commission of September 16, 2005 amending Directive 91/414 / EEC.
  9. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Chlorotoluron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.