4-甲基-1,2,3-噻二唑-5-羧酸有机锡和苯并[1,2,3]噻二唑-7-羧酸有机锡的合成与生物活性。

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

机构信息

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.

出版信息

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

DOI:10.1021/jf902168d

PMID:20014765

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)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.

摘要

一系列的有机锡 4-甲基-1,2,3-噻二唑-5-羧酸酯和苯并[1,2,3]噻二唑-7-羧酸酯已经被合成并通过 NMR ((1)H, (13)C, 和 (119)Sn)、IR 和元素分析进行了表征。二聚体复合物 {(BTHCO(2))SnEt(2)O}(2)（BTH 代表苯并[1,2,3]噻二唑-7-基）的结构进一步通过 X 射线衍射晶体学得到了确认。杀菌活性评估表明，所有新合成的化合物对茄丝核盘菌、花生褐斑病菌、禾谷镰孢菌、梨叶点霉和灰葡萄孢都表现出良好的生长抑制作用。在体外，三有机锡 4-甲基-1,2,3-噻二唑-5-羧酸酯和苯并[1,2,3]噻二唑-7-羧酸酯在 50μg/mL 时获得了高的生长抑制率。这些三有机锡羧酸酯的相应 EC(50)值已经被检测到，并且三乙基锡苯并[1,2,3]噻二唑-7-羧酸酯对梨叶点霉的 EC(50)值低至 0.12μg/mL，对禾谷镰孢菌的 EC(50)值低至 0.16μg/mL。