Fluometuron

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Structural formula
Structural formula of fluometuron
General
Surname Fluometuron
other names
  • N , N -dimethyl- N '- [3- (trifluoromethyl) phenyl] urea
  • Cotoran
Molecular formula C 10 H 11 F 3 N 2 O
Brief description

white crystals

External identifiers / databases
CAS number 2164-17-2
EC number 218-500-4
ECHA InfoCard 100,016,819
PubChem 16562
Wikidata Q5462798
properties
Molar mass 232.20 g mol −1
Physical state

firmly

Melting point

163-164.5 ° C

solubility

very sparingly soluble in water (0.11 g l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 302-332-319-410
P: 261-273-280-304 + 340-305 + 351 + 338-312
Toxicological data

> 8000 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 .

Fluometuron is a chemical compound from the group of phenylureas . It was introduced as a herbicide by Ciba (now Syngenta ) in 1960 .

Extraction and presentation

Fluometuron can be obtained from toluene . This is photochlorinated and then fluorinated to benzotrifluoride . This is nitrated and then hydrogenated. The intermediate product 3-aminobenzotrifluoride now reacts with phosgene and dimethylamine to form fluometuron.

use

Estimated US application rate in 2011

Fluometuron is used as a selective, systemic herbicide in cotton and sugar cane cultivation. In the USA in 2011 (exclusively in cotton cultivation) around 400 t were consumed.

It works by inhibiting photosystem II , in addition to which the carotenoid biosynthesis is blocked.

Admission

In some EU countries, plant protection products with this active ingredient are approved, but not in Germany, Austria or Switzerland.

Individual evidence

  1. ↑ a b c d e f g Entry on Fluometuron. In: Römpp Online . Georg Thieme Verlag, accessed on July 27, 2014.
  2. ↑ a b Entry on fluometuron in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
  3. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 236 ( limited preview in Google Book search).
  4. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Fluometuron in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 25, 2016.