数字农科院2.0

Synthesis, Fungicidal Activity, and Action Mode Investigations of Novel Nitrophenyl (Z)-3,3-Diaryl Acrylates

文献类型： 外文期刊

作者： Yin, Fahong;Chen, Minghui;Chen, Shuning;Hong, Sai;Yan, Xiaojing;Xiao, Yumei;Qin, Zhaohai

作者机构：

关键词： fungicidal activity;uncoupler;phenyl acrylate;transcriptome;biodegradation

期刊名称： JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

ISSN： 0021-8561

年卷期： 2025 年 73 卷 32 期

页码：

收录情况： SCIE（2025版） ; ; EI（2025版）

摘要： Uncoupling agents involved in the oxidative phosphorylation process are a category of bioactive molecules that have garnered significant attention; however, their applications in agriculture remain limited. In this study, we employed a scaffold-hopping strategy to design and synthesize a new class of phenyl acrylates. This was achieved by substituting the methylacryloyl group in dinocap with 3,3-diarylacryloyl derivatives featuring a pyridine ring, which shows affinity for mitochondrial respiratory chain complexes. Through fungicidal activity evaluations, we identified compounds such as Ia-7, Ib-7, and Ic-7 that exhibit significantly greater activity compared to meptyl dinocap. Notably, the EC50 of Ia-7's protective effect against wheat powdery mildew was 3.98 mu g/mL, slightly higher than that of fluopyram (3.17 mu g/mL) but considerably lower than that of fluazinam (10.04 mu g/mL), indicating its potential as a candidate fungicide. Structure-activity relationship analysis revealed that the pK a value of the phenolic unit is a crucial factor influencing its activity, although it is not the sole determinant. This suggests that it may function as a prodrug, similar to binapacryl, primarily via the release of phenol with uncoupling activity. Other molecular components also contribute to the overall activity, as made evident by the rapid biodegradation of Ib-7. Analyses of biodegradable products, transcriptomic profiles, and ATPase activity indicate that the mechanisms of action of these compounds are intricate, predominantly centered on oxidative phosphorylation. As an uncoupling agent, their mode of action shares both similarities and differences with fluazinam.

分类号：

  • 相关文献

[1]Isolation, identification, and degradation mechanism by multi-omics of mesotrione-degrading Amycolatopsis nivea La24. Qingqing Li,Qingyun Ma,Yiqing Zhou,Xu Jiang,Rebecca E. Parales,Shumiao Zhao,Yan Zhuang,Zhiyong Ruan. 2024

[2]Molecular mechanism underlying the degradation of tetracycline by Apiotrichum loubieri MFZ-16. Wang J.,Zhang M.,Cheng J.,Han Y.,Ma H.,Jiang X.,Liu Y.. 2024

[3]Isolation and characterization of polycyclic aromatic hydrocarbons-degrading Sphingomonas sp strain ZL5. Liu, YS,Zhang, J,Zhang, ZZ.

[4]Synthesis and biological activities of 2-oxocycloalkylsulfonamides. Yang, Xinling,Liang, Xiaomei,Kai, Zhenpeng,Yuan, Dekai,Zhang, Jianjun,Ling, Yun,Chen, Fuheng,Wang, Daoquan,Yuan, Huizu,Qi, Shuhua,Wang, Ruiqing,Ran, Fuxiang. 2008

[5]Synthesis and Fungicidal Activity of 2-Alkylaminosulfonyl-5,6-dihydro-dibenzo[b,e]azephine-6,11-dione. . 2014

[6]Synthesis and Evaluation of Novel N-(4 '-Arylpyrimidin-2 '-yl) Sulfonylurea Derivatives as Potential Antifungal Agents. Chen Wei,Li Yuxin,Wei Wei,Chen Youwei,Li Yonghong,Liu Jingbo,Li Zhengming,Chen Wei,Li Yuxin,Wei Wei,Chen Youwei,Liu Jingbo,Li Zhengming,Shi Yanxia,Li Baoju. 2015

[7]Synthesis and fungicidal activity of macrolactams and macrolactones with an oxime ether side chain. Jia, Yue-Mei,Liang, Xiao-Mei,Zhu, Wei-Juan,Zhang, Jian-Jun,Dong, Yan-Hong,Wu, Jin-Ping,Chen, Fu-Heng,Wang, Dao-Quan,Yuan, Hui-Zu,Qi, Shu-Hua. 2007

[8]Transaldolase gene Ta167 enhances the biocontrol activity of Clonostachys rosea 67-1 against Sclerotinia sclerotiorum. Li, Shi-Dong,Sun, Man-Hong.

[9]Synthesis and fungicidal activities of a novel series of 4-[3-(Pyrid-4-yl)-3-substituted phenyl acryloyl] morpholine. Yuan Hui-Zhu,Li Nan,Fu Bin,Xiao Yu-Mei,Ma Yong-Qiang,Qi Shu-Hua,Qin Zhao-Hai. 2007

[10]Microwave Assistant Synthesis, Antifungal Activity and DFT Theoretical Study of Some Novel 1,2,4-Triazole Derivatives Containing Pyridine Moiety. Sun, Guo-Xiang,Wu, Hong-Ke,Yang, Ming-Yan,Sun, Zhao-Hui,Liu, Xing-Hai,Shi, Yan-Xia,Li, Bao-Ju,Zhang, Yong-Gang. 2014

[11]Utilization of Chitosan-Lactide Copolymer Nanoparticles as Controlled Release Pesticide Carrier for Pyraclostrobin Against Colletotrichum gossypii Southw. Huang, Qi-Liang,Xu, Lei,Cao, Li-Dong,Li, Feng-Min,Wang, Xiang-Jing.

[12]Design, synthesis and fungicidal activity of 11-alkoxyimino-5,6-dihydro-dibenzo[b,e] azepine-6-one derivatives. Xu, Yan-jun,Huang, Jia-xing,Liang, Xiao-mei,Zhang, Jian-jun,Wang, Dao-quan,Yan, Xiao-jing,Yuan, Hui-zhu.

[13]Design, Synthesis, and Fungicidal Activity of Macrolactones and Macrolactams with a Sulfonamide Side Chain. Wu, Peng,Liang, Xiao-Mei,Dong, Yan-Hong,Zhang, Jian-Jun,Meng, Xiang-Qing,Wu, Jin-Ping,Chen, Fu-Heng,Wang, Dao-Quan,Yuan, Hui-Zu,Qi, Shu-Hua.

[14]Synthesis, Fungicidal Activity, and Structure-Activity Relationship of Spiro-Compounds Containing Macrolactam (Macrolactone) and Thiadiazoline Rings. Li, Jian-Jun,Liang, Xiao-Mei,Jin, Shu-Hui,Zhang, Jian-Jun,Chen, Fu-Heng,Wang, Dao-Quan,Yuan, Hui-Zhu,Qi, Shu-Hua.

[15]Synthesis and Fungicidal Activity of Aryl Carbamic Acid-5-aryl-2-furanmethyl Ester. Li, Ying,Ling, Yun,Miao, Hong-Jian,Yang, Xin-Ling,Li, Bao-Ju,Shi, Yan-Xia.

[16]Synthesis and Biological Activity of Some Novel Trifluoromethyl-Substituted 1,2,4-Triazole and Bis(1,2,4-Triazole) Mannich Bases Containing Piperazine Rings. Shi, Yan-Xia,Li, Bao-Ju,Wang, Bao-Lei,Ma, Yi,Liu, Xing-Hai,Li, Yong-Hong,Song, Hai-Bin,Li, Zheng-Ming.

[17]Synthesis and Fungicidal Activity of Novel 2,5-Disubstituted-1,3,4-oxadiazole Derivatives. Cui, Zi-Ning,Zhang, Li,Ling, Yun,Yang, Xin-Ling,Shi, Yan-Xia,Li, Bao-Ju,Cui, Zi-Ning,Nishida, Yoshihiro. 2012

[18]Design, Synthesis, Biological Activities, and 3D-QSAR of New N,N '-Diacylhydrazines Containing 2-(2,4-dichlorophenoxy)propane Moiety. Liu, Xing-Hai,Weng, Jian-Quan,Tan, Cheng-Xia,Pan, Li,Ma, Yi,Li, Yong-Hong,Li, Zheng-Ming,Shi, Yan-Xia,Li, Bao-Ju,Zhang, Yong-Gang. 2011

[19]Synthesis and Fungicidal Activities of Azaindolyl Thiazoline Compounds. Xiao Yumei,Yuan Dekai,Zhang Zhenhua,Fu Bin,Yan Xiaojing,Yuan Huizhu. 2016

[20]Synthesis and Fungicidal Activities of Biaryl Methanone O-Benzyl Oximes. Wan Chuan,Du Shijie,Li Hong,Jiang Jiazhen,Xiao Yumei,Qin Zhaohai,Yuan Huizhu. 2015

作者其他论文 更多>>