dithiocarbamate

Dithiocarbamates are a class of organosulfur compounds derived from amines and carbon disulfide. The hallmark is the dithiocarbamate moiety, typically represented as R2N–C(=S)–S− in salt form or R2N–C(=S)–SH for the neutral thiocarbamic acid. In salts the anion commonly coordinates to metals as a bidentate ligand through the two sulfur atoms, though binding modes vary with metal and substituents. The dithiocarbamate anion is resonance-stabilized, contributing to the stability of a wide range of derivatives.

Preparation typically involves reacting carbon disulfide with primary or secondary amines in the presence of a base, producing dialkyl or diaryl dithiocarbamate salts that can be isolated as metal salts or free bases. This versatile route allows the synthesis of many substituted derivatives, including both aliphatic and aromatic examples.

Applications span coordination chemistry, agriculture, and materials science. As ligands, dithiocarbamates form stable metal complexes and are widely used in catalysis and materials research due to their strong, tunable sulfur donation. In agriculture, several dithiocarbamate fungicides are widely used, including maneb, mancozeb, zineb, and ziram, which are typically administered as metal-containing dithiocarbamate complexes. They also find use as stabilizers and additives in polymers and rubber, and as precursors to other sulfur-containing compounds. Some derivatives can be toxic and are subject to regulatory controls.