Dithiocarbamates

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General structure of the dithiocarbamates

As dithiocarbamates (also dithiourethanes be mentioned) ester and salts (and their derivatives ) of the dithiocarbamic acid , respectively. They are disulfur analogs of carbamates . Their general structure is R 1 - N (--R 2 ) - C (= S) - S - R 3 , where R 1 , R 2 and R 3 stand for interchangeable radicals. They are often used in agriculture as fungicides , herbicides and insecticides , but in the chemical industry they are also used as vulcanization accelerators. They are generally poorly soluble both in water and (with a few exceptions) in common organic solvents . They arise from the reaction of carbon disulfide with ammonia and primary and secondary amines .

synthesis

Dithiocarbamates are formed from isothiocyanates and thioalcohols through an addition reaction:

Preparation of dithion urethanes from isothiocyanates and mercaptans

Derivatives

  • Dazomet C 5 H 10 N 2 S 2 is used as a crop protection agent
  • Disulfiram (TETD) C 10 H 20 N 2 S 4 , is used to treat alcoholism and as a vulcanization accelerator
  • Dithiocarb C 5 H 10 NS 2 Na is as chelator used
  • Ferbam C 9 H 18 FeN 3 S 6 is, as a fungicide used
  • Mancozeb C 4 H 6 MnN 2 S 4 ; C 4 H 6 ZnN 2 S 4 , is used as a fungicide
  • Maneb C 4 H 6 N 2 S 4 · Mn is used as a fungicide
  • Metam C 2 H 5 NS 2 or metam sodium C 2 H 5 NS 2 Na, is as a fungicide, herbicide and nematicide used
  • Methylmetiram C 10 H 20 N 5 S 8 Zn, is as a fungicide used
  • Metiram C 16 H 33 N 11 S 16 Zn 3 mixed precipitation, is used as a fungicide
  • Nabam C 4 H 6 N 2 Na 2 S 4 , is used as a herbicide, algicide and fungicide
  • Propineb (C 5 H 8 N 2 S 4 Zn) x , is used as a fungicide
  • Thiram (TMTD) C 6 H 12 N 2 S 4 , is used as a fungicide and vulcanization accelerator
  • Zineb C 4 H 6 N 2 S 4 Zn is used as a fungicide
  • Ziram C 6 H 12 N 2 S 4 Zn, is used as a fungicide and vulcanization accelerator

Web links

Individual evidence

  1. ^ THE PPDB Pesticide Properties Database (see Mancozeb, Maneb, Metiram, Thiram et al.). Retrieved May 4, 2016 .
  2. ↑ Max Bögemann, Siegfried Petersen, Otto-Erich Schultz and Hanna Söll: Methods for the production and conversion of sulfur-containing carbonic acid derivatives in Houben-Weyl : Methods of Organic Chemistry , Volume 9, Georg Thieme Verlag, Stuttgart, 1955, pages 773-915, there Page 831.
  3. ↑ External identifiers of or database links to Metam : CAS number: 144-54-7, EC number: 205-632-2, ECHA InfoCard: 100.005.121 , PubChem : 3001858 , ChemSpider : 2273120 , Wikidata : Q16747480 .
  4. ↑ External identifiers or database links for methylmetiram : CAS number: 8064-35-5, Wikidata : Q98002799 .