Dichlofluanid

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Structural formula
Structural formula of dichlofluanid
General
Surname Dichlofluanid
other names
  • N - (dichlorofluoromethylthio) - N ′, N ′ -dimethyl- N -phenylsulfamide ( IUPAC )
  • 1,1-dichloro- N - [(dimethylamino) sulfonyl] -1-fluoro- N -phenyl-methanesulfenamide
  • N - (dichlorofluoromethylthio) - N ', N ' -dimethyl- N -phenylsulfonyl-diamide
  • N - (dichlorofluoromethylthio) - N ′, N ′ -dimethyl- N -phenylsulfamide
  • Euparen
Molecular formula C 9 H 11 Cl 2 FN 2 O 2 S 2
Brief description

colorless, crystalline powder

External identifiers / databases
CAS number 1085-98-9
EC number 214-118-7
ECHA InfoCard 100.012.835
PubChem 14145
ChemSpider 13520
Wikidata Q421444
properties
Molar mass 333.23 g mol −1
Physical state

firmly

density

1.575 g cm −3 

Melting point

105 ° C 

Vapor pressure

0.14 mPa (20 ° C)

solubility

practically insoluble in water: 0.0013 g l −1 (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: 332-319-317-400
P: 261-273-280-302 + 352 + 312-304 + 340 + 312-501
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dichlofluanid is an organic chemical compound that is contained as an active ingredient in fungicides for fruit and plant cultivation and in wood preservatives .

history

Dichlofluanid was developed by Bayer AG and brought onto the market in 1965. Up until 2003, the manufacturer did not apply for a new approval in accordance with Directive 91/414 / EEC of the Council of the European Community, so that the active ingredient was practically withdrawn from the market.

Presentation and extraction

The compound is synthesized by reacting anilinodimethylaminosulfone with dichlorofluoromethanesulfenyl chloride in the presence of triethylamine .

Synthesis of dichlofluanide

Dichlorofluoromethylsulfenyl chloride can be obtained by a chlorine-fluorine exchange from trichloromethanesulfenyl chloride by means of magnesium fluoride or silver (I) fluoride .

properties

The compound forms colorless crystals that melt at 105 ° C. A boiling point could not be observed. Sublimation is observed above 120 ° C. The compound is only very sparingly soluble in water. At pH4 it is 0.92 mg l −1 at 10 ° C, 1.58 mg l −1 at 20 ° C and 2.69 mg l −1 at 30 ° C. The solubility in the range of pH 4 - 9 does not depend on the pH value. The hydrolysis takes place at higher pH values. Significantly better solubility is observed in organic solvents. This is in xylene 81.2 g · l -1 , in 2-methyl-2,4-pentanediol 20.7 g · l -1 and in propylene glycol dimethyl ether 86.4 g · l -1 . As a metabolite of fungicide that arises dimethylsulfamide .

use

The active ingredient was used under the trade name Euparen in the cultivation of ornamental plants against gray mold , against rose powdery mildew , against leaf fall disease , against late blight and brown rot on tomatoes and against powdery mildew in cucumber .

Admission

Dichlofluanid is not a permitted active ingredient in plant protection products in the European Union. In Germany, Austria and Switzerland dichlofluanid is not contained in any approved pesticides.

It has a biocide approval in the EEA and Switzerland as an antifouling agent until December 31, 2025.

Individual evidence

  1. ↑ a b c d e Entry on dichlofluanid in the GESTIS substance database of the IFA , accessed on August 5, 2012(JavaScript required) .
  2. ↑ a b c d e f Directive 98/8 / EC concerning the placing of biocidal products on the market, Assessment Report Dichlofluanid
  3. ↑ a b c Entry on diclofluanid. In: Römpp Online . Georg Thieme Verlag, accessed on 10 March 2014 .
  4. ↑ Entry on dichlofluanid 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. ↑ Datasheet Dichlofluanid, PESTANAL at Sigma-Aldrich , accessed on May 18, 2017 ( PDF ).
  6. ↑ Decision of the Commission of April 17, 2002 declaring a concentration to be compatible with the common market and the EEA Agreement (Case COMP / M.2547 - Bayer / Aventis Crop Science), p. 76. (PDF)
  7. ↑ Council Directive of July 15, 1991 on the placing of plant protection products on the market (91/414 / EEC) .
  8. ↑ patent BE609868, Farbensabricken Bayer AG 1,963th
  9. ↑ Kober, E .: A New Class of Sulfenyl Derivatives; Perhalogenated Aliphatic Sulfenyl Fluorides in J. Am. Chem. Soc. 81 (1959) 4810-4812, doi : 10.1021 / ja01527a016 .
  10. ↑ Ham, NS: Dichlorofluoromethanesulfenyl chloride in J. Am. Chem. Soc. 83 (1961) 751-752, doi : 10.1021 / ja01464a052 .
  11. ↑ PAN Pesticides Database - Chemicals: N, N-Dimethylsulfamide (metabolite of tolylfluanid).
  12. ↑ Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 extending the deadline in accordance with Article 8 paragraph 2 of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this directive and the revocation of Approvals of plant protection products with these active ingredients (PDF) .
  13. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on dichlofluanid in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.
  14. ↑ Dichlofluanid - Information on biocides - ECHA. Retrieved on August 18, 2019 (German).

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