Design, Synthesis, and Antifungal Activities of Novel Aromatic Carboxamides Containing a Diphenylamine Scaffold

2019 ◽  
Vol 67 (17) ◽  
pp. 5008-5016 ◽  
Author(s):  
Aigui Zhang ◽  
Ying Yue ◽  
Jian Yang ◽  
Jiaxing Shi ◽  
Ke Tao ◽  
...  
Keyword(s):  
Design Synthesis ◽  
Antifungal Activities

Design, Synthesis and Antifungal Activity of Novel 1-(Adamantan-1-yl) ethanone Oxime Esters

2020 ◽  
Vol 17 (5) ◽  
pp. 526-532
Author(s):  
Si Liu ◽  
Li-Zhi Niu ◽  
Yan-Hua Shi ◽  
Fu-Xian Wan ◽  
Lin Jiang
Keyword(s):  
Antifungal Activity ◽  
Biological Activities ◽  
Lead Compound ◽  
Design Synthesis ◽  
Antifungal Activities

Background: Oxime compounds, including oxime ethers and oxime esters, possess various biological activities. Many oxime ethers have been widely used in the fields of pesticides and medicines. However, oxime ethers are rarely used in the field of pesticides. Methods: We chose the excellent fungicide pyrifenox as the lead compound, integrated pyridinyl, adamantyl and benzoyl moieties into one molecule, while also designed and synthesized ten 1- (adamantan-1-yl)ethanone oxime esters containing pyridinyl moiety. Moreover, we also evaluated their preliminary antifungal activities against S. sclerotiorum and B. cinerea. Results: The target compounds were characterized by NMR, IR and HRMS. The preliminary bioactivity test showed that they exhibited some antifungal activity to S. sclerotiorum and B. cinerea, and EC50 values were in the range of 14.16-32.97 and 27.60-52.82 μg/mL, respectively. Conclusion: Some target compounds such as 3d, 3e, 3h and 3i, exhibited moderate activities against S. sclerotiorum, with EC50 values of 14.16-18.18 μg/mL.

scholarly journals Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5852
Author(s):  
Hui Bai ◽  
Xuelian Liu ◽  
Pengfei Chenzhang ◽  
Yumei Xiao ◽  
Bin Fu ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Binding Modes ◽  
Oxime Ether ◽  
Single Crystal Diffraction ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Triazole Derivatives ◽  
Pyridine Moiety ◽  
New Compounds

A series of novel 1,2,4-triazole derivatives containing oxime ether and phenoxy pyridine moiety were designed and synthesized. The new compounds were identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). Compound (Z)-1-(6-(4-nitrophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a18) was further confirmed by X-ray single crystal diffraction. Their antifungal activities were evaluated against eight phytopathogens. The in vitro bioassays indicated that most of the title compounds displayed moderate to high fungicidal activities. Compound (Z)-1-(6-(4-bromo-2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a4) exhibited a broad-spectrum antifungal activities with the EC50 values of 1.59, 0.46, 0.27 and 11.39 mg/L against S. sclerotiorum, P. infestans, R. solani and B. cinerea, respectively. Compound (Z)-1-(6-(2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-benzyl oxime (5b2) provided the lowest EC50 value of 0.12 mg/L against S. sclerotiorum, which were comparable to the commercialized difenoconazole. Moreover, homologous modeling and molecular docking disclosed possible binding modes of compounds 5a4 and 5b2 with CYP51. This work provided useful guidance for the discovery of new 1,2,4-triazole fungicides.

ChemInform Abstract: Design, Synthesis and Antifungal Activities of Novel Pyrrole Alkaloid Analogues.

ChemInform ◽  
2011 ◽  
Vol 42 (31) ◽  
pp. no-no
Author(s):  
Ming-Zhong Wang ◽  
Han Xu ◽  
Tuan-Wei Liu ◽  
Qi Feng ◽  
Shu-Jing Yu ◽  
...  
Keyword(s):  
Design Synthesis ◽  
Antifungal Activities

scholarly journals Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2203 ◽  
Author(s):  
Peiqi Chen ◽  
Xiangmin Song ◽  
Yongmei Fan ◽  
Weihao Kong ◽  
Hao Zhang ◽  
...  
Keyword(s):  
Phytopathogenic Fungi ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
In Vivo Experiments ◽  
Sar Studies ◽  
Low Toxicity ◽  
Inhibitory Activities ◽  
Commercial Pesticide ◽  
Pipiens Pallens

In order to find pesticides with insecticidal and antifungal activities, a series of novel benzoyl pyrimidinylurea derivatives were designed and synthesized. All target compounds were identified by 1H-NMR spectroscopy and HRMS. Insecticidal and antifungal activity of these compounds were evaluated and the structure-activity relationships (SAR) were clearly and comprehensively illustrated. Compound 7, with low toxicity to zebrafish (LC50 = 378.387 µg mL−1) showed 100% inhibition against mosquito (Culex pipiens pallens) at 0.25 µg mL−1. Both compounds 19 and 25 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 13 phytopathogenic fungi), which were better than those of the commercial pesticide pyrimethanil (>50% inhibitory activities against eight phytopathogenic fungi). Furthermore, compounds 19 and 25 exhibited protective activity against Sclerotinia sclerotiorum on leaves of Brassica oleracea L. during in vivo experiments.

scholarly journals Design, Synthesis, and Antimicrobial Evaluation of Novel Pyrazoles and Pyrazolyl 1,3,4-Thiadiazine Derivatives

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2092 ◽  
Author(s):  
Ibrahim Radini
Keyword(s):  
Antimicrobial Activity ◽  
Minimum Inhibitory Concentration ◽  
Elemental Analysis ◽  
Inhibitory Concentration ◽  
Diazonium Salts ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Antibacterial And Antifungal Activities ◽  
Antimicrobial Evaluation ◽  
Antibacterial And Antifungal

A novel series of pyrazolyl 1,3,4-thiadiazines 5a–c, 8a–c, 12, 15a–c, 17a–c, and 20 was prepared from the reaction of pyrazole-1-carbothiohydrazide 1a,b with 2-oxo-N′-arylpropanehydrazonoyl chloride, 2-chloro-2-(2-arylhydrazono)acetate, and 3-bromoacetylcoumarin. Moreover, the regioselective reaction of 5-pyrazolone-1-carbothiohydrazide 1a with 4-substituted diazonium salts and 4-(dimethylamino)benzaldehyde gave the corresponding hydrazones 21a–c and 22. The newly prepared compounds were characterized by spectroscopy and elemental analysis. Many new synthesized compounds showed considerable antimicrobial activity against tested microorganisms. Hydrazones 21a–c and 22 showed remarkable antibacterial and antifungal activities. 4-(2-(p-tolyl)hydrazineylidene)-pyrazole-1-carbothiohydrazide 21a displayed the highest antibacterial and antifungal activities with minimum inhibitory concentration (MIC) values lower than standard drugs chloramphenicol and clotrimazole, in the range of 62.5–125 and 2.9–7.8 µg/mL, respectively.

Design, Synthesis, Antifungal Activities and SARs of (R)-2-Aryl-4,5-dihydrothiazole-4-carboxylic Acid Derivatives

2015 ◽  
Vol 33 (11) ◽  
pp. 1269-1275 ◽  
Author(s):  
Jingbo Liu ◽  
Yuxin Li ◽  
Youwei Chen ◽  
Xuewen Hua ◽  
Yingying Wan ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Design Synthesis ◽  
Antifungal Activities
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