Synthesis and biological activity of organotin 4-methyl-1,2,3-thiadiazole-5-carboxylates and benzo[1,2,3]thiadiazole-7-carboxylates

J Agric Food Chem. 2010 Mar 10;58(5):2715-9. doi: 10.1021/jf902168d.

Abstract

A series of organotin 4-methyl-1,2,3-thiadiazole-5-carboxylates and benzo[1,2,3]thiadiazole-7-carboxylates have been synthesized and characterized by NMR ((1)H, (13)C, and (119)Sn), IR, and elemental analyses. The structure of the dimeric complex {[(BTHCO(2))SnEt(2)](2)O}(2) (BTH represents benzo[1,2,3]thiadiazol-7-yl) has been further confirmed by X-ray diffraction crystallography. Assessment for fungicidal activity indicates that all of the newly synthesized compounds exhibit good growth inhibition against Alternaria solani , Cercospora arachidicola , Gibberella zeae , Physalospora piricola , and Botrytis cinerea . High growth inhibition percentage at 50 microg/mL was obtained in vitro in the case of triorganotin 4-methyl-1,2,3-thiadiazole-5-carboxylates and benzo[1,2,3]thiadiazole-7-carboxylates. The corresponding EC(50) values of these triorganotin carboxylates have been detected, and values of EC(50) as low as 0.12 microg/mL against P. piricola and 0.16 microg/mL against G. zeae, respectively, were observed for triethyltin benzo[1,2,3]thiadiazole-7-carboxylate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemistry*
  • Crystallography, X-Ray
  • Fungi / drug effects
  • Models, Molecular
  • Organotin Compounds / chemical synthesis*
  • Organotin Compounds / chemistry
  • Organotin Compounds / pharmacology*
  • Thiadiazoles / chemical synthesis*
  • Thiadiazoles / chemistry
  • Thiadiazoles / pharmacology*

Substances

  • Carboxylic Acids
  • Organotin Compounds
  • Thiadiazoles