Benzimidazole

Colorless crystals

Fixed

171-174 ° C

> 360 ° C

  • Slightly soluble in water (2 g · l-1 at 20 ° C)
  • Soluble in ethanol

2910 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Benzimidazole is a heterocyclic organic chemical compound that results from the fusion of benzene and imidazole. Compounds with this basic structure are referred to as benzimidazoles, whose most important representative in nature the compound N- ribosyl dimethylbenzimidazole is, which occurs as a ligand for cobalt in vitamin B12. But it is also in connection with purine and adenine in which benzene is replaced by a pyrimidine.

Production and representation

Benzimidazole can be represented by the condensation of o-phenylenediamine with formic acid or trimethyl orthoformate in the equivalents.

Use

Benzimidazole is used as a starting material for the preparation of derivatives derived therefrom. These are used as drugs ( eg omeprazole, Flubendazole, domperidone ), anthelmintic (ATC P02CA eg albendazole ), plastics (eg polybenzimidazole ) and dyes (eg, Benzimidazolone ).

They are also used as fungicides (MBC fungicides ) where the mechanism of action is based on the inhibition of cell division ( mitosis) by destroying the components of the spindle apparatus. Since this is just a point of the metabolism of the fungus, and therefore there is a high risk of resistance. This group includes, among other agents with activity against eyespot and snow mold. They have a healing ( curative ) but no preventive ( protective ) effect. Some of these derivatives are:

  • Carbendazim ( eg fungicide Harvesan and mordants )
  • Thiophanate-methyl (such as Cercobin )
  • Fuberidazol (eg in seed dressings )
  • Benomyl ( no longer allowed)
  • Fenbendazole
  • Mebendazole
  • Thiabendazole

Where is the actual active ingredient carbendazim and thiophanate -methyl and benomyl be converted into the plant to carbendazim. This compounds such netobimin and febantel are included as such no benzimidazole structure, but these are formed from the substances in the body, called Probenzimidazole.

CAS registry number PubChem Condensation reaction Polybenzimidazole fiber Fuberidazole Tiabendazole
116214
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