Design, Synthesis and Insecticidal Activity of New Phenylpyrazole Derivatives

doi:10.6023/cjoc202405024

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (1): 227-239.DOI: 10.6023/cjoc202405024 Previous Articles Next Articles

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新型苯基吡唑类衍生物的设计、合成和杀虫活性研究

田海平^a, 刘东东^a^,^b, 裴鸿艳^a^,^c, 叶家麟^a, 郑子锐^a, 高一星^a, 李昌兴^a, 田欢^a, 张静^a^,^b^,^d^,^*(), 张立新^a^,^b^,^c^,^d^,^*()

a 沈阳化工大学功能分子研究所沈阳 110142
b 辽宁科技大学化学工程学院辽宁鞍山 114051
c 沈阳工业大学材料科学与工程学院沈阳 110870
d 广西思钺生物科技有限责任公司南宁 530000

收稿日期:2024-05-16 修回日期:2024-08-05 发布日期:2024-09-18
作者简介:
†共同第一作者
基金资助:
国家自然科学基金(22277081); 辽宁省自然科学基金计划(2022-KF-15-04); 辽宁省“揭榜挂帅”科技攻关计划(2022JH1/10400018)

Design, Synthesis and Insecticidal Activity of New Phenylpyrazole Derivatives

Haiping Tian^a, Dongdong Liu^a^,^b, Hongyan Pei^a^,^c, Jialin Ye^a, Zirui Zheng^a, Yixing Gao^a, Changxing Li^a, Huan Tian^a, Jing Zhang^a^,^b^,^d(), Lixin Zhang^a^,^b^,^c^,^d()

a Institute of Functional Molecules, Shenyang University of Chemical Technology, Shenyang 110142
b School of Chemical Engineering, University of Science and Technology Liaoning, Anshan, Liaoning 114051
c School of Materials Science and Engineering, Shenyang University of Technology, Shenyang 110870
d Guangxi Siyue Biotechnology Co., Ltd., Nanning 530000

Received:2024-05-16 Revised:2024-08-05 Published:2024-09-18
Contact: *E-mail: zhang-jing@syuct.edu.cn; zhanglixin@syuct.edu.cn
About author:
†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22277081); Natural Science Foundation Program of Liaoning Province(2022-KF-15-04); “Jiebang Guashuai” Science and Technology Tackling Plan of Liaoning Province(2022JH1/10400018)

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Abstract

To enhance the discovery of phenylpyrazole-based insecticides and acaricides with superior biological activity, leveraging the insecticide and acaricide of Nicoflurole as a lead compound, 25 novel phenylpyrazole analogues were designed and synthesized through the design strategies of bioelectronic rearrangement and active substructures splicing. The target compounds were confirmed by ¹H NMR, ¹³C NMR and HRMS. The insecticidal activities against Tetranychus cinnabarinus, Myzus persicae, and Plutella xylostella were preliminarily screened and rescreened to preliminarily explore structure-activity relationship. Among them, methyl 1-(2-chloro-5-(1-(2,6-dichloro-4-(perfluoropropan-2-yl)phenyl)-1H-pyrazol-4-yl)nicotin- amido)cyclopropane-1-carboxylate (8e) showed 100% mite killing efficacy against Tetranychus cinnabarinus at 2.5 mg/L. 5-(1-(2-Bromo-6-chloro-4-(perfluoropropan-2-yl)phenyl)-1H-pyrazol-4-yl)-2-chloro-N-cyclopropylnicotinamide (8i) exhibited an insecticidal efficacy of 100% against Myzus persicae at 5 mg/L. 2-Chloro-N-cyclopropyl-5-(1-(2,6-dichloro-4-(perfluoro-propan-2-yl)phenyl)-1H-pyrazol-4-yl)-N-methylbenzamide (8a), 2-chloro-N-cyclopropyl-5-(1-(2,6-dichloro-4-(perfluoropro- pan-2-yl)phenyl)-1H-pyrazol-4-yl)benzamide (8b), and 8i demonstrated an insecticidal efficacy of 100% against Plutella xylostella at 2.5 mg/L. Molecular docking studies indicated that the enhancement of 8e acaricidal activity may be due to the incorporation of ester groups leading to an increase in corresponding hydrogen bonding interactions. This study provides valuable insights for the continued optimization and development of novel phenylpyrazole insecticides and acaricides.

Key words: phenylpyrazole, insecticidal activity, structure-activity relationship, molecular docking

Cite this article

Haiping Tian, Dongdong Liu, Hongyan Pei, Jialin Ye, Zirui Zheng, Yixing Gao, Changxing Li, Huan Tian, Jing Zhang, Lixin Zhang. Design, Synthesis and Insecticidal Activity of New Phenylpyrazole Derivatives[J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 227-239.

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Compd.	Tetranychus cinnabarinus		Myzus persicae		Plutella xylostella
Compd.	100 mg/L	10 mg/L	100 mg/L	10 mg/L	100 mg/L	10 mg/L
8a	56.3	34.4	0	0	100	100
8b	—	85.4	—	40	100	100
8c	—	0	—	0	—	90
8d	—	0	—	41.7	—	68.9
8e	100	100	0	0	100	69.8
8f	100	31.6	0	0	100	13.3
8g	89.5	81.2	0	0	36.7	0
8h	0	0	0	0	100	0
8i	100	100	100	100	100	100
8j	100	100	100	100	100	100
8k	0	0	0	0	73.3	0
8l	0	0	0	0	0	0
8m	0	0	0	0	0	0
8n	0	0	0	0	0	0
8o	0	0	0	0	0	0
8p	0	0	0	0	0	0
8q	0	0	0	0	0	0
8r	0	0	0	0	0	0
8s	0	0	0	0	0	0
8t	0	0	0	0	0	0
8u	0	0	0	0	0	0
8v	0	0	0	0	0	0
8w	0	0	0	0	0	0
8x	0	0	0	0	20.7	0
8y	0	0	0	0	0	0
Nicofluprole	100	100	100	87.2	100	100
CK1	100	100	100	100	100	100

Compd.	Tetranychus cinnabarinus		Myzus persicae		Plutella xylostella
Compd.	100 mg/L	10 mg/L	100 mg/L	10 mg/L	100 mg/L	10 mg/L
8a	56.3	34.4	0	0	100	100
8b	—	85.4	—	40	100	100
8c	—	0	—	0	—	90
8d	—	0	—	41.7	—	68.9
8e	100	100	0	0	100	69.8
8f	100	31.6	0	0	100	13.3
8g	89.5	81.2	0	0	36.7	0
8h	0	0	0	0	100	0
8i	100	100	100	100	100	100
8j	100	100	100	100	100	100
8k	0	0	0	0	73.3	0
8l	0	0	0	0	0	0
8m	0	0	0	0	0	0
8n	0	0	0	0	0	0
8o	0	0	0	0	0	0
8p	0	0	0	0	0	0
8q	0	0	0	0	0	0
8r	0	0	0	0	0	0
8s	0	0	0	0	0	0
8t	0	0	0	0	0	0
8u	0	0	0	0	0	0
8v	0	0	0	0	0	0
8w	0	0	0	0	0	0
8x	0	0	0	0	20.7	0
8y	0	0	0	0	0	0
Nicofluprole	100	100	100	87.2	100	100
CK1	100	100	100	100	100	100

Compd.	Mortality rate/%
Compd.	5 mg/L	2.5 mg/L	1.25 mg/L
8b	22.2	0	0
8e	100	100	54.6
8i	100	95.3	71.6
8j	100	84.9	13.2
Nicofluprole	71	44	20.4
CK1	98.6	61.9	34.7

Compd.	Mortality rate/%
Compd.	5 mg/L	2.5 mg/L	1.25 mg/L
8b	22.2	0	0
8e	100	100	54.6
8i	100	95.3	71.6
8j	100	84.9	13.2
Nicofluprole	71	44	20.4
CK1	98.6	61.9	34.7

Compd.	Mortality rate/%
Compd.	5 mg/L	2.5 mg/L	1.25 mg/L
8i	100	31.1	10.2
8j	72.2	45	24.3
Nicofluprole	50.9	26.1	14.7
CK1	80.2	74.0	14.3

新型苯基吡唑类衍生物的设计、合成和杀虫活性研究

Design, Synthesis and Insecticidal Activity of New Phenylpyrazole Derivatives

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