2-(2-Chloro-6-methylpyridin-3-yl)-5-(4-methylthiadiazol-5-yl)-1,3,4-oxadiazole | 945856-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(2-Chloro-6-methylpyridin-3-yl)-5-(4-methylthiadiazol-5-yl)-1,3,4-oxadiazole
• CAS: 945856-59-7
• 化学式: C₁₁H₈ClN₅OS
• 分子量: 293.736
• InChiKey: FZCWLSKHIGUDSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氯-6-甲基烟酸 、 4-甲基-1,2,3-噻二唑-5-羧酸酰肼 在 三氯氧磷 作用下， 反应 6.0h， 以48%的产率得到2-(2-Chloro-6-methylpyridin-3-yl)-5-(4-methylthiadiazol-5-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and Biological Activity Evaluation of 1,2,3-Thiadiazole Derivatives as Potential Elicitors with Highly Systemic Acquired Resistance

  摘要：

  Elicitors provide a broad spectrum of systemic acquired resistance by altering the physical and physiological status of the host plants and, therefore, are among the most successful directions in modern pesticide development for plant protection. To develop a novel elicitor with highly systemic acquired resistance, two series of thiazole- and oxadiazole-containing thiadiazole derivatives were rationally designed and synthesized according to the principle of combination of bioactive substructures in this work. Their structures were characterized by (1)H nuclear magnetic resonance (NMR), infrared (IR), high-resolution mass spectrometry (HRMS), or elemental analysis. Their potential systemic acquired resistance as an elicitor was also evaluated; bioassay results indicated that, among the 23 compounds synthesized, three compounds, 10a, 10d, and 12b, displayed better systemic acquired resistance than the positive control, tiadinil, a commercialized 1,2,3-thiadiazole-based elicitor. In addition, three other compounds, 10f, 12c, and 12j, exhibited a certain degree of fungus growth inhibition in vitro or in vivo. Our results demonstrated that, in combination of bioactive substructures is an interesting exploration for novel pesticide development, thiazole- and oxadiazole-containing thiadiazole derivatives are potential elicitors with good systemic acquired resistance.

  DOI：

  10.1021/jf8031364

文献信息

• Synthesis and Biological Activity Evaluation of 1,2,3-Thiadiazole Derivatives as Potential Elicitors with Highly Systemic Acquired Resistance
  作者：Zhijin Fan、Zugui Shi、Haike Zhang、Xiufeng Liu、Lili Bao、Lin Ma、Xiang Zuo、Qinxiang Zheng、Na Mi

  DOI：10.1021/jf8031364

  日期：2009.5.27

  Elicitors provide a broad spectrum of systemic acquired resistance by altering the physical and physiological status of the host plants and, therefore, are among the most successful directions in modern pesticide development for plant protection. To develop a novel elicitor with highly systemic acquired resistance, two series of thiazole- and oxadiazole-containing thiadiazole derivatives were rationally designed and synthesized according to the principle of combination of bioactive substructures in this work. Their structures were characterized by (1)H nuclear magnetic resonance (NMR), infrared (IR), high-resolution mass spectrometry (HRMS), or elemental analysis. Their potential systemic acquired resistance as an elicitor was also evaluated; bioassay results indicated that, among the 23 compounds synthesized, three compounds, 10a, 10d, and 12b, displayed better systemic acquired resistance than the positive control, tiadinil, a commercialized 1,2,3-thiadiazole-based elicitor. In addition, three other compounds, 10f, 12c, and 12j, exhibited a certain degree of fungus growth inhibition in vitro or in vivo. Our results demonstrated that, in combination of bioactive substructures is an interesting exploration for novel pesticide development, thiazole- and oxadiazole-containing thiadiazole derivatives are potential elicitors with good systemic acquired resistance.