Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing 1,3,4-Oxadiazole Group

doi:10.6023/cjoc202212021

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1584-1590.DOI: 10.6023/cjoc202212021 Previous Articles Next Articles

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新型含1,3,4-噁二唑基团的吡唑肟衍生物的合成与生物活性

孙洋, 王杨, 张紫婵, 钱烨, 骆桂成, 周贝贝, 缪丽沙, 陈雨蝶, 戴红^*(), 徐宝琳, 吴正光^*()

南通大学化学化工学院江苏南通 226019

收稿日期:2022-12-15 修回日期:2023-01-31 发布日期:2023-02-06
通讯作者: 戴红, 吴正光
作者简介:
^†共同第一作者.
基金资助:
国家自然科学基金(22177057); 江苏省大学生创新训练计划(202210304022Z)

Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing 1,3,4-Oxadiazole Group

Yang Sun, Yang Wang, Zichan Zhang, Ye Qian, Guicheng Luo, Beibei Zhou, Lisha Miao, Yudie Chen, Hong Dai(), Baolin Xu, Zhengguang Wu()

College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019

Received:2022-12-15 Revised:2023-01-31 Published:2023-02-06
Contact: Hong Dai, Zhengguang Wu
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22177057); Science and Technology Innovation Foundation for the College Students of Jiangsu Province(202210304022Z)

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Abstract

In order to explore new pyrazole oxime compounds possessing satisfactory bioactivities, sixteen pyrazole oxime derivatives containing 1,3,4-oxadiazole group were prepared with fenpyroximate selected as lead structure. Their insecticidal activities were determined. Preliminary bioassay demonstrated that all the target compounds displayed 100% insecticidal activities towards Mythimna separata at 500 μg/mL, of which 5 target compounds possessed 80%~100% insecticidal activities against Mythimna separata at 100 μg/mL. Moreover, at concentration of 500 μg/mL, mortality rates against Aphis medicaginis of 9 target compounds were 100%, those of 3 compounds were 70%~100% at 100 μg/mL. Additionally, 4 target compounds exhibited more than 80% mortality rates against Tetranychus cinnabarinus at 500 μg/mL.

Key words: 1,3,4-oxadiazole, pyrazole oxime, synthesis, bioactivity

Cite this article

Yang Sun, Yang Wang, Zichan Zhang, Ye Qian, Guicheng Luo, Beibei Zhou, Lisha Miao, Yudie Chen, Hong Dai, Baolin Xu, Zhengguang Wu. Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing 1,3,4-Oxadiazole Group[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1584-1590.

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References 35

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Entry	Acid scavenger	Solvent	Temp./℃	Yield/%
1	Pyridine	Acetone	Reflux	0
2	Et₃N	Acetone	Reflux	0
3	Na₂CO₃	Acetone	Reflux	23
4	K₂CO₃	Acetone	Reflux	32
5	Cs₂CO₃	Acetone	Reflux	36
6	Pyridine	MeCN	Reflux	20
7	Et₃N	MeCN	Reflux	25
8	Na₂CO₃	MeCN	Reflux	41
9	K₂CO₃	MeCN	Reflux	62
10	Cs₂CO₃	MeCN	Reflux	68
11	Na₂CO₃	DMF	80	39
12	K₂CO₃	DMF	80	52
13	Cs₂CO₃	DMF	80	55

Entry	Acid scavenger	Solvent	Temp./℃	Yield/%
1	Pyridine	Acetone	Reflux	0
2	Et₃N	Acetone	Reflux	0
3	Na₂CO₃	Acetone	Reflux	23
4	K₂CO₃	Acetone	Reflux	32
5	Cs₂CO₃	Acetone	Reflux	36
6	Pyridine	MeCN	Reflux	20
7	Et₃N	MeCN	Reflux	25
8	Na₂CO₃	MeCN	Reflux	41
9	K₂CO₃	MeCN	Reflux	62
10	Cs₂CO₃	MeCN	Reflux	68
11	Na₂CO₃	DMF	80	39
12	K₂CO₃	DMF	80	52
13	Cs₂CO₃	DMF	80	55

Compd.	Mythimna separata			Aphis medicaginis			Tetranychus cinnabarinus
Compd.	500 μg/mL	100 μg/mL	20 μg/mL	500 μg/mL	100 μg/mL	20 μg/mL	500 μg/mL	100 μg/mL
8a	100	80	0	100	60	0	0	—
8b	100	0	—	100	0	—	0	—
8c	100	100	50	100	70	0	80	0
8d	100	0	—	100	0	—	0	—
8e	100	0	—	0	—	—	0	—
8f	100	60	0	100	0	—	0	—
8g	100	100	50	100	100	40	90	0
8h	100	0	—	0	—	—	0	—
8i	100	0	—	0	—	—	0	—
8j	100	0	—	100	0	—	0	—
8k	100	80	0	0	—	—	0	—
8l	100	70	0	0	—	—	100	0
8m	100	0	—	100	0	—	0	—
8n	100	60	0	0	—	—	0	—
8o	100	0	—	0	—	—	0	—
8p	100	100	40	100	90	30	100	0
Tolfenpyrad	100	50	40	—	—	—	—	—
Imidacloprid	—	—	—	100	100	100	—	—
Fenpyroximate	—	—	—	—	—	—	100	100

Compd.	Mythimna separata			Aphis medicaginis			Tetranychus cinnabarinus
Compd.	500 μg/mL	100 μg/mL	20 μg/mL	500 μg/mL	100 μg/mL	20 μg/mL	500 μg/mL	100 μg/mL
8a	100	80	0	100	60	0	0	—
8b	100	0	—	100	0	—	0	—
8c	100	100	50	100	70	0	80	0
8d	100	0	—	100	0	—	0	—
8e	100	0	—	0	—	—	0	—
8f	100	60	0	100	0	—	0	—
8g	100	100	50	100	100	40	90	0
8h	100	0	—	0	—	—	0	—
8i	100	0	—	0	—	—	0	—
8j	100	0	—	100	0	—	0	—
8k	100	80	0	0	—	—	0	—
8l	100	70	0	0	—	—	100	0
8m	100	0	—	100	0	—	0	—
8n	100	60	0	0	—	—	0	—
8o	100	0	—	0	—	—	0	—
8p	100	100	40	100	90	30	100	0
Tolfenpyrad	100	50	40	—	—	—	—	—
Imidacloprid	—	—	—	100	100	100	—	—
Fenpyroximate	—	—	—	—	—	—	100	100

新型含1,3,4-噁二唑基团的吡唑肟衍生物的合成与生物活性

Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing 1,3,4-Oxadiazole Group

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