Synthesis and biological activity of organotin 4-methyl-1,2,3-thiadiazole-5-carboxylates and benzo[1,2,3]thiadiazole-7-carboxylates.
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.
Wang
Zhi-Hong
ZH
State Key Laboratory of Elemento-Organic Chemistry, The Research Institute of Elemento-Organic Chemistry, Nankai University, No. 94 Weijin Road, Nankai District, Tianjin 300071, People's Republic of China. zhihongwang@nankai.edu.cn
Guo
Yan-Zhao
YZ
Zhang
Jun
J
Ma
Lin
L
Song
Hai-Bin
HB
Fan
Zhi-Jin
ZJ
D002264:Carboxylic Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005658:Fungi / Q000187:drug effects; D008958:Models, Molecular; D009947:Organotin Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D002264:Carboxylic Acids; D009947:Organotin Compounds; D013830:Thiadiazoles