Dithiocarbamate
A dithiocarbamate is a functional group in organic chemistry. It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms. Sodium diethyldithiocarbamate is a common example. Dithiocarbamates and their derivatives are widely used in the vulcanization of rubber.[1]
Formation and reactions
Many primary and secondary amines react with carbon disulfide and sodium hydroxide to form dithiocarbamate salts:[1]
- R2NH + CS2 + NaOH → R2NCS2−Na+ + H2O
Ammonia reacts with CS2 similarly:
- 2 NH3 + CS2 → H2NCS2−NH4+
Dithiocarbamate salts are pale colored solid that are soluble in water and polar organic solvents.
Applications
Zinc dithiocarbamates are used to modify the crosslinking of certain polyolefins with sulfur, a process called vulcanization. They are used as ligands for chelating metals.[2]
Dithiocarbamates specifically ethylene bisdithiocarbamates, EBDCs, in the form of complexes with manganese (maneb), zinc (zineb) or a combination of manganese and zinc (mancozeb), have been used extensively as fungicides in agriculture from the 1940s.[3][4]
See also
References
- ↑ 1.0 1.1 Hans-Wilhelm Engels et al., "Rubber, 4. Chemicals and Additives" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a23_365.pub2
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ http://www.apsnet.org/publications/apsnetfeatures/Pages/Fungicides.aspx
- ↑ Gullino, Maria Lodovica, et al. "Mancozeb: past, present, and future." Plant Disease 94.9 (2010): 1076-1087.
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