Dialate

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Structural formula
Structure of dialate
( Z ) isomer
General
Surname Dialate
other names
  • S - (2,3-dichloroallyl) - N , N -diisopropylthiocarbamate
  • N , N -diisopropylthiocarbamic acid S - (2,3-dichloro-2-propenyl) ester
  • DDTC
  • DATC
  • 2,3-DCDT
  • Di-Allate
Molecular formula C 10 H 17 Cl 2 NOS
Brief description

brownish solid

External identifiers / databases
CAS number
  • 2303-16-4
  • 17708-58-6 ( E ) -diallate
  • 17708-57-5 ( Z ) -diallate
EC number 218-961-1
ECHA InfoCard 100.017.238
PubChem 28700
Wikidata Q61637544
properties
Molar mass 270.22 g · mol -1
Physical state

firmly

density

1.89 g cm −3

Melting point

25-30 ° C

boiling point

150 ° C (12 h Pa )

Vapor pressure

0.00015 mmHg (25 ° C)

solubility

bad in water

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
08 - Dangerous to health 07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 302-351-410
P: ?
Toxicological data

395 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 .

Diallat is an active ingredient for crop protection from the group of thiocarbamates . In more detail, dialate is a mixture of two isomeric chemical compounds:

  • ( E ) - S - (2,3-dichloroallyl) - N , N -diisopropylthiocarbamate and
  • ( Z ) - S - (2,3-dichloroallyl) - N , N -diisopropylthiocarbamate.

history

Diallat was launched in 1961 by Monsanto under the name Avadex .

Extraction and presentation

Dialate can be obtained from carbonyl sulfide and diisopropylamine , which react with one another in the presence of sodium hydroxide . Their product reacts with 1,2,3-trichloropropene to form dialate.

use

Diallat is used as a herbicide in the cultivation of barley, corn, alfalfa , clover, lentils, peas, potatoes and sugar beets. It works mainly against unwanted grasses.

Admission

In the EU countries such as Germany and Austria as well as Switzerland no diallate-containing is pesticides approved.

safety instructions

Diallat is classified as carcinogenic.

See also

Individual evidence

  1. ↑ a b c d e Entry on Diallat in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
  2. ^ Entry on Diallat in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on June 16, 2017.
  3. ↑ Data sheet of the New Jersey Department of Health (English) .
  4. ↑ Entry on Di-allate 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. ↑ Entry on dialate in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  6. ↑ Peter Mair, John E. Casida: Diallate, Triallate, and Sulfallate Herbicides: Identification of Thiocarbamate Sulfoxides, Chloroacroleins, and Chloroallylthiols as Mouse Microsomal Oxidase and Glutathione S-Transferase Metabolites, J. Agric. Food Chem. 1991, 39, pp. 1504-1508.
  7. ↑ Entry on Diallat. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2019.
  8. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 104 ( limited preview in Google Book search).
  9. ↑ Diallat's mission profile .
  10. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Di-allate in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.
  11. ^ Office of Environmental Health Hazard Assessment California ( Memento from July 20, 2007 in the Internet Archive ) (PDF; 632 kB).
  12. ^ Directory of carcinogenic, mutagenic substances .