Isoprothiolane

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of isoprothiolane
General
Surname Isoprothiolane
other names
  • Diisopropyl 2- (1,3-dithiolan-2-ylidene) malonate
  • Fuji-one
Molecular formula C 12 H 18 O 4 S 2
Brief description
  • colorless crystals
  • in technical quality: yellow solid
External identifiers / databases
CAS number 50512-35-1
EC number 610-537-8
ECHA InfoCard 100.124.256
PubChem 39681
Wikidata Q18816455
properties
Molar mass 290.40 g mol −1
Physical state

firmly

Melting point
  • 54-54.5 ° C ° C
  • 50–51 ° C (technical quality)
solubility

practically insoluble in water (0.054 g l −1 at 25 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Isoprothiolane is a chemical compound from the group of dithiolanes and 1974 by Nihon Noyaku introduced fungicide . Isoprothiolane has a noticeable ketene di thioacetal structure.

Extraction and presentation

Isoprothiolane can be prepared from diisopropylmalonate , which reacts with carbon disulfide in the presence of sodium hydride . The product reacts further with 1,2-dibromoethane to form isoprothiolane.

use

Isoprothiolane is a systemic fungicide with curative and protective effects. The active ingredient is used in rice cultivation to combat various fungal diseases such as rice blight .

It is also used to treat fatty liver syndrome in cattle.

Admission

No plant protection products containing this active ingredient are permitted in the EU or Switzerland .

Individual evidence

  1. ↑ a b c d e f Entry on isoprothiolane. In: Römpp Online . Georg Thieme Verlag, accessed on January 8, 2015.
  2. ↑ a b Isoprothiolane data sheet from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
  3. ↑ Hiroki Ota: Historical Development of Pesticides in Japan, pp. 80-81.
  4. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 734 ( limited preview in Google Book search).
  5. ↑ Takashi Hirooka, Yukio Miyagi, Fujio Araki, Hitoshi Kunoh, Hiroshi Ishizaki: The effect of isoprothiolane on the emergence of infection pegs from appressoria of Pyricularia oryzae . In: Pesticide Science . tape 13 , no. 4 , August 1982, p. 379-386 , doi : 10.1002 / ps.2780130407 .
  6. ↑ Y. Shimada, H. Katamoto, S. Ishida, K. Kobayashi, H. Tohzyoh: Therapeutic effect of isoprothiolane on bovine fat necrosis. In: Nihon juigaku zasshi. The Japanese journal of veterinary science. Volume 50, Number 5, October 1988, ISSN  0021-5295 , pp. 1017-1024, PMID 3199611 .
  7. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on Isoprothiolane in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 26, 2016.