Bian Qiang, Zhao Rui-Qi, Peng Xing-Jie, Gao Li-Jie, Zhou Guo-Na, Yu Shu-Jing, Zhao Wei-Guang
National Pesticide Engineering Research Center (Tianjin), State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
College of Animal Science & Technology, Forestry College, Hebei Agricultural University, Baoding 071000, China.
J Agric Food Chem. 2021 Apr 7;69(13):3848-3858. doi: 10.1021/acs.jafc.0c07581. Epub 2021 Mar 29.
To explore the influence of the positions of the two nitrogen atoms on the thiazole ring and the isoxazoline ring on the activity, a series of novel piperidyl thiazole derivatives containing oxime ether and oxime ester moieties with two nitrogen atoms on the same or opposite sides have been designed, synthesized, and first evaluated for their fungicidal activities against . The bioassay results showed that the target compounds possessed moderate to good fungicidal activities against , among which oxime ether compound shows the highest fungicidal activity (EC = 0.0104 μg/mL) which is higher than dimethomorph (EC = 0.1148 μg/mL) and diacetylenyl amide (EC = 0.040 μg/mL). Compared with oxime ether compounds (the two nitrogen atoms are on the opposite sides), the activities of oxime ester compounds were significantly reduced. It is different from the commercial fungicide fluoxapiprolin, and the activities of the compounds with the two nitrogen atoms on the same side were significantly reduced compared to the compounds with the two nitrogen atoms on the opposite sides. Moreover, compounds , , , and showed moderate to good antifungal activities against , and . Scanning electron microscopy of compound on the hyphae morphology showed that compound might cause mycelial abnormalities of .
为了探究噻唑环和异恶唑啉环上两个氮原子的位置对活性的影响，设计、合成了一系列在噻唑环和异恶唑啉环上含有肟醚和肟酯部分且两个氮原子位于同侧或异侧的新型哌啶基噻唑衍生物，并首次对其针对……的杀菌活性进行了评估。生物测定结果表明，目标化合物对……具有中等至良好的杀菌活性，其中肟醚化合物……表现出最高的杀菌活性（EC = 0.0104 μg/mL），高于烯酰吗啉（EC = 0.1148 μg/mL）和联苯吡菌胺（EC = 0.040 μg/mL）。与肟醚化合物（两个氮原子位于异侧）相比，肟酯化合物的活性显著降低。这与市售杀菌剂氟唑菌酰羟胺不同，且两个氮原子位于同侧的化合物的活性相较于两个氮原子位于异侧的化合物显著降低。此外，化合物……、……、……和……对……、……和……表现出中等至良好的抗真菌活性。对化合物……在菌丝形态上进行扫描电子显微镜观察表明，化合物……可能导致……的菌丝异常。
