3,7-二甲基辛-2,6-二烯酰胺和3,7-二甲基-6,7-二羟基辛-2-烯酰胺的合成及杀菌活性
收稿日期: 2021-05-07
修回日期: 2021-05-31
网络出版日期: 2021-06-22
基金资助
国家自然科学基金(21772229)
Synthesis and Fungicidal Activity of Novel 3,7-Dimethylocta-2,6-dienamides and 3,7-Dimethyl-6,7-dihydroxyoct-2-enamides
Received date: 2021-05-07
Revised date: 2021-05-31
Online published: 2021-06-22
Supported by
National Natural Science Foundation of China(21772229)
分别以(Z)-和(E)-香叶醇为原料, 设计合成了22个新的(Z)-和(E)-3,7-二甲基辛-2,6-二烯酰胺及光学活性(6R或6S)-3,7-二甲基-6,7-二羟基辛-2-烯酰胺, 它们的结构经过IR, 1H NMR, 13C NMR和HR-ESI-MS表征. 离体杀菌活性测试结果显示, 部分化合物在50 µg/mL浓度时对水稻纹枯菌和油菜菌核菌等测试植物病原菌显示了一定的杀菌活性, 如(Z)-N-[2-(4-氯苯基)苯基]-3,7-二甲基辛-2,6-二烯酰胺(5d)、(6S,2Z)-N-[2-(4-氯苯基)苯基]-3,7-二甲基-6,7-二羟基辛-2-烯酰胺(7g)和(6R,2Z)-N-[2-(4-氯苯基)苯基]-3,7-二甲基-6,7-二羟基辛-2-烯酰胺(7h)对油菜菌核菌的EC50分别为46.3, 38.1和40.6 µg/mL, (Z)-N-(4-叔丁基苄基)-3,7-二甲基辛-2,6-二烯酰胺(5b)对水稻纹枯菌的EC50分别为20.5 µg/mL. 活体杀菌活性测试结果显示, 在400 µg/mL浓度下(Z)-N-(2-氯-4-三氟甲基苯基)-3,7-二甲基辛-2,6-二烯酰胺(5c)、(E)-N-(2-氯-4-三氟甲基苯基)-3,7-二甲基辛-2,6-二烯酰胺(5g)和(6S,2E)-N-(2-氯-4-三氟甲基苯基)-3,7-二甲基-6,7-二羟基辛-2-烯酰胺(7m)对黄瓜霜霉病和小麦白粉病的防效达到50%~100%, 具有进一步优化提高杀菌活性的潜力.
王卫伟 , 李益豪 , 刘鑫磊 , 赵宇 , 王明安 . 3,7-二甲基辛-2,6-二烯酰胺和3,7-二甲基-6,7-二羟基辛-2-烯酰胺的合成及杀菌活性[J]. 有机化学, 2021 , 41(9) : 3717 -3725 . DOI: 10.6023/cjoc202105009
A series of novel (Z)- and (E)-3,7-dimethylocta-2,6-dienamides and optical (6R or 6S)-3,7-dimethyl-6,7-dihydroxyoct-2-enamides were designed and synthesized using (Z)- and (E)-geraniols as raw materials, respectively. Their structures were characterized by IR, 1H NMR, 13C NMR and HR-ESI-MS spectra. The preliminary bioassay results indicated that some compounds exhibit certain in vitro fungicidal activities against Rhizoctonia solani and Sclerotinia sclerotiorum at the concentration of 50 µg/mL. For example, (Z)-N-(2-(4-chlorophenyl)phenyl)-3,7-dimethylocta-2,6-dienamide (5d), (6S,2Z)-N-(2- (4-chlorophenyl)phenyl)-3,7-dimethyl-6,7-dihydroxyoct-2-enamide (7g) and (6S,2Z)-N-(2-(4-chlorophenyl)phenyl)-3,7-dimethyl-6,7-dihydroxyoct-2-enamide (7h) have EC50 values of 46.3, 38.1 and 40.6 µg/mL against S. sclerotiorum, and (Z)-N-(4-tert-butyl-benzyl)-3,7-dimethylocta-2,6-dienamide (5b) has an EC50 value of 20.5 µg/mL against R. solani, respectively. The in vivo efficacy of (Z)-N-(2-chloro-4-trifluromethylphenyl)-3,7-dimethylocta-2,6-dienamide (5c), (E)-N-(2-chloro- 4-trifluromethylphenyl)-3,7-dimethylocta-2,6-dienamide (5g) and (6S,2E)-N-(2-chloro-4-trifluromethylphenyl)-3,7-dimethyl- 6,7-dihydroxyoct-2-enamide (7m) at the concentration of 400 µg/mL were in the range of 50%~100% against Pseudoperonospora cubensis and Erysiphe graminis. They have a potential to be optimized for improving the fungicidal activity.
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