1,2,3-噻二唑联-1,2,4-三唑衍生物的合成及抑菌活性

杨知昆; 张海科; 范志金; 米娜; 宋海斌; 孙学军; NataliaP.Belskaia; VasiliyA.Bakulev

1,2,3-噻二唑联-1,2,4-三唑衍生物的合成及抑菌活性

1.
南开大学元素有机化学国家重点实验室,天津 300071
2.
曲阜师范大学化学科学学院,山东曲阜 273165
3.
TOSLab,The Urals State Technical University,620002,Ekaterinburg,Russia

基金项目:

国家自然科学基金(20672062,20872071);国家自然科学基金国际合作项目(No.29);天津市自然科学基金(07JCYBJC01200);天津市科技支撑计划国际科技合作项目(07ZCGHHZ01400)资助.

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出版历程
- 收稿日期: 2008-12-10

Synthesis and Fungicidal Activity of 1,2,3-ThiadiazoleContaining 1,2,4-Triazoles

1.
State Key Laboratory of Elemento-organic Chemistry,Nankai University,Tianjin 300071,China
2.
Department of Chemistry,Qufu Normal University,Qufu 273165,Shandong Province,China
3.
TOSLab,The Urals State Technical University,620002,Ekaterinburg,Russia

摘要

摘要: 以4-氨基-3-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑-5-硫酮为原料,与醛在冰乙酸中回流制得15个新型4-取代亚氨基-3-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑-5-硫酮化合物,其结构经IR、1H NMR 及元素分析表征,其中,化合物 5c 的结构经单晶测试确证,该晶体属单斜晶系,P2(1)/c空间群,晶胞参数a=1.403 7(3) nm,b=1.570 5(3) nm,c=0.686 4(14) nm,β=102.06(3)°,V = 1.479 8(5) nm3,Z=4,F(000)=656。初步的抑菌活性测试结果表明;所有化合物对黄瓜灰霉病菌Botrytis cinerea都有较好的抑制作用,化合物 5l 的抑制率达87%, 5c、5d和5f 的抑制率在78%左右; 5a 对小麦赤霉病菌Gibberella zeae的抑制率为78.7%; 5m 对西瓜炭疽病菌Colletotrichum lagenarium的抑制率为65.6%。
- 1,2,3-噻二唑 /
- 1,2,4-三唑 /
- 合成 /
- 杀菌活性 /
- 单晶结构
Abstract: Fifteen novel title compounds were synthesized from 3-(4-methyl-1,2,3-thiadiazolyl)-4- amino-1,2,4-triazolo-5-thione with substituted benzaldehyde in acetic acid under refluxing.The structures of the compounds were confirmed by elemental analysis,IR and 1H NMR.The single crystal of compound 5c was cultured and determined by X-ray single-crystal diffraction as of a monoclinic system,space group P2(1)/c with cell parameters a=1.403 7(3) nm, b=1.570 5 (3) nm,c=0.686 4 (4) nm,β= 102.06 (3)°,V=1.479 8(9) nm3 ,Z=4,F(000)=656.Bioassay was conducted by fungi growth inhibition method using 10 commonly used fungi which represented most disease occurring in China,the results showed that,all the title compounds had satisfactory fungicidal activity against Botrytis cinerea,the growth inhibition rate of compound 5l against Botrytis cinerea was up to 87%,for compound 5c,5d and 5f were more than 78%,compound 5a exhibited fungicidal activity against Gibberella zeae with growth inhibition of 78.7%,the growth inhibition rate of compound 5m against Colletotrichum lagenarium was 65.6%.
- 1,2,3-thiadiazole /
- 1,2,3-triazole /
- synthesis /
- fungicide activity /
- single crystal structure

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参考文献(12)

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