Design, Synthesis, and Insecticidal Activity of Novel m-Diamide Compounds Containing Sulfur

被引:0
作者
Huang, Pengmian [1 ]
Yang, Hualan [1 ]
Wu, Minghui [2 ]
Zhou, Liqi [2 ]
Huang, Zihan [2 ]
Liu, Jiyong [2 ]
机构
[1] Changsha Univ Sci & Technol, Sch Chem & Chem Engn, Changsha, Peoples R China
[2] CAC Nantong Chem Co Ltd, Nantong, Peoples R China
关键词
cyproflanilide; insecticidal activity; m-diamide; molecular docking; sulfur; META-DIAMIDE; BROFLANILIDE; MODES;
D O I
10.1002/cbdv.202500230
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
To find efficient insecticides with novel structures, 16 novel m-diamide compounds containing sulfur were designed and synthesized based on the principle of biologically active factor splicing with cyproflanilide as the lead compound. Preliminary biological assay data showed that some of the target compounds exhibited insecticidal activity above 90% against Mythimna separata at 0.01 mg/L and Aphis craccivora at 100 mg/L, which were better than cyproflanilide. Meanwhile, most compounds still maintain 100% mortality at 1 mg/L for Plutella xylostella. In particular, compounds 5c, 5e, 5f, and 5g revealed excellent activities against P. xylostella, M. separata, and A. craccivora, exhibiting efficient and broad-spectrum insecticidal activity. Additionally, the interaction between the metabolites of cyproflanilide, compound 5g, and gamma-aminobutyric acid receptor protein was studied by molecular docking method. The results showed that they could be stably bound to the potential active cavity in the protein to form a protein-ligand complex, thus showing excellent insecticidal activity, which is consistent with the data on the excellent insecticidal activity of compounds. This work showed that sulfur-containing compounds might provide certain clues for structure optimization for the development of new insecticides.
引用
收藏
页数:8
相关论文
共 32 条
[1]  
[成升魁 Cheng Shengkui], 2021, [中国科学基金, Bulletin of National Natural Science Foundation of China], V35, P426
[2]   Sulfur-Containing Agrochemicals [J].
Devendar, Ponnam ;
Yang, Guang-Fu .
TOPICS IN CURRENT CHEMISTRY, 2017, 375 (06)
[3]   Exploring the Interaction Mechanism of Desmethyl-broflanilide in Insect GABA Receptors and Screening Potential Antagonists by In Silico Simulations [J].
Gao, Ya ;
Zhang, Yichi ;
Wu, Fengshou ;
Pei, Jianfeng ;
Luo, Xiaogang ;
Ju, Xiulian ;
Zhao, Chunqing ;
Liu, Genyan .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2020, 68 (50) :14768-14780
[4]   Status and outlook for acaricide and insecticide discovery [J].
Jeschke, Peter .
PEST MANAGEMENT SCIENCE, 2021, 77 (01) :64-76
[5]   Discovery of broflanilide, a novel insecticide [J].
Katsuta, Hiroyuki ;
Nomura, Michikazu ;
Wakita, Takeo ;
Daido, Hidenori ;
Kobayashi, Yumi ;
Kawahara, Atsuko ;
Banba, Shinichi .
JOURNAL OF PESTICIDE SCIENCE, 2019, 44 (1-2) :120-128
[6]  
Kobayshi Y., 2010, WO2010013567
[7]   Influence of new sulfur-containing fertilizers on performance of wheat yield [J].
Kurmanbayeva, Meruyert ;
Sekerova, Tolganai ;
Tileubayeva, Zhanar ;
Kaiyrbekov, Tursynbek ;
Kusmangazinov, Adil ;
Shapalov, Shermakhan ;
Madenova, Aigul ;
Burkitbayev, Mukhambetkali ;
Bachilova, Nadezhda .
SAUDI JOURNAL OF BIOLOGICAL SCIENCES, 2021, 28 (08) :4644-4655
[8]  
Li W., 2022, WO2024023735
[9]  
Liu J. Y., 2021, World Pesticide, V43, P34, DOI DOI 10.16201/J.CNKI.CN10-1660/TQ.2021.01.05
[10]   Reliability Assessment of Cyber Physical Distribution System [J].
Liu, Jie ;
Wang, Diangang ;
Zhang, Cheng ;
Tang, Zhenyu ;
Jiang, Zhuozhen ;
Liu, Junyong ;
Xiang, Yue .
PROCEEDINGS OF THE 9TH INTERNATIONAL CONFERENCE ON APPLIED ENERGY, 2017, 142 :2021-2026