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Dichlobenil

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Structural formula
Strukturformel von Dichlobenil
General
Name Dichlobenil
Other names
  • 2,6-Dichlorobenzonitrile
  • Casoron
Sum formula C7H3Cl2N
Brief description

light grey powder[1] with characteristic odour[2]

External identifiers/databases
CAS number 1194-65-6
EC number 214-787-5
ECHA InfoCard 100.013.443
PubChem 3031
ChemSpider 2923
Wikidata Q416231
Features
Molar mass 172.01 g-mol-1
State of aggregation

synced and corrected by elderman — – for —

Density

1.349 g-cm-3[1]

Melting point

144–145 °C[1]

Boiling point

270 °C[1]

Vapour pressure

0.073 Pa (20 °C)[2]

Solubility

practically insoluble in water (0.02 g-l-1 at 20 °C)[1]

Safety instructions
GHS hazardous substance labelling from Regulation (EC) No 1272/2008 (CLP),[3] extended if necessary[1]

07 – Achtung 09 – Umweltgefährlich

Attention

H and P phrases H 312– ‐411
P 273– ‐280 [1]
Toxicological data
  • 2710 mg-kg-1 (LD50, rat, oral)[1]
  • 1350 mg-kg-1 (LD50, rabbit, transdermal)[1]
SI units are used wherever possible and customary. Unless otherwise stated, the data given are valid for standard conditions.

Dichlobenil is a chemical compound from the group of nitriles and organic chlorine compounds.

History

Dichlobenil was discovered in the mid-1950s and its herbicidal properties were studied in the 1960s. It was found to be very potent in suppressing germination.[4]

Extraction and presentation

Dichlobenil can be obtained by the reaction of 2,6-dichlorobenzaldehyde with hydroxylamine.[5]

Features

Dichlobenil is a combustible solid which is practically insoluble in water.[1]

Use

Dichlobenil has been used as a herbicide. Its half-life in the open is about 60 days.[4] In the soil, it is formed, among other things, during the degradation of chlorothiamide.[6]

Approval

In Germany, the approval of the agent was revoked by the Federal Office of Consumer Protection and Food Safety (BVL) on 23 August 2004.[7]

In Switzerland, dichlobenil was removed from the authorisation list as of 1 February 2013; here it had been used in the cultivation of ornamental shrubs and in forestry plant nurseries. After expiry of the one-year period, its sale and use has been banned since 1 February 2014.[8]

No plant protection products containing dichlobenil as an active ingredient are available in the EU countries including Germany and Austria as well as in Switzerland.[9]

Individual references

  1. a b c d e f g h i j Entry for Dichlobenil in the IFA’s GESTIS substance database, retrieved 14 February 2017 (JavaScript required).
  2. a b International Chemical Safety Card (ICSC) for Dichlobenil at the National Institute for Occupational Safety and Health (NIOSH), retrieved 9 December 2014
  3. Entry for Dichlobenil in the Classification and Labelling Inventory of the European Chemicals Agency (ECHA), retrieved 1 February 2016. Manufacturers or distributors may extend the harmonised classification and labelling.
  4. a b V S Rao: Principles of Weed Science, Second Edition. Taylor & Francis, 2000, ISBN 978-1-578-08069-4, p. 87 (limitedpreview in Google Book Search).
  5. Thomas A. Unger: Pesticide Synthesis Handbook. Elsevier Science, 1996, ISBN 978-0-080-95716-6, p. 820 (limited preview in Google Book Search).
  6. Beynon, K. I.; Wright, A. N.: Persistence, Penetration, and Breakdown of Chlorthiamide and Dichlobenil Herbicides in Field Soils of Different Types, in J. Sc. Fd. Agric. 1968, 19, 718–722.
  7. General ruling on the return of plant protection products containing the active substance dichlobenil(Memento of 19 April 2009 in the Internet Archive).
  8. Federal Department of Economic Affairs Ordinance on the Placing of Plant Protection Products on the Market, amendment of 11 December 2012.
  9. European Commission Directorate-General for Health and Food Safety: entry on Dichlobenil in the EU Pesticides Database; entry in the national plant protection product directories of Switzerland, Austriaand Germany, retrieved8 March 2016.