Synthesis and <i>in vivo</i> fungicidal activity of some new quinoline derivatives against rice blast

Liu, Xinghai; Fang, Yue-Ming; Xie, Feng; Zhang, Ruirui; Shen, Zhonghua; Tan, Cheng‐Xia; Weng, Jian‐Quan; Xu, Tian‐Ming; Huang, Hongying

doi:10.1002/ps.4556

Cited by 52 publications

(30 citation statements)

References 24 publications

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“…In our previous work , we found the perfluoropropanyl group on the quinoline ring can increase the fungicidal activity, so in line with our continued efforts to synthesize novel lead compounds for drug discover , the fungicide tebufloquin was selected as a lead compound, the t ‐Bu group was replaced by perfluoropropanyl group, and the fluorine atom was replaced by hydrogen atom. Then, the ether group was replaced by ester carbonate.…”

Section: Introductionmentioning

confidence: 95%

Synthesis and Biological Activity of Some New 6‐perfluoropropanyl Quinoline Derivatives

Zhang

et al. 2018

Journal of Heterocyclic Chem

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A series of new quinoline derivatives containing perfluoropropanyl moiety were designed and synthesized. Their structures were confirmed by 1 H NMR, MS, and elemental analysis. The bioassay results showed that some of them exhibited good control efficacy against Pyricularia oryae. Also, some of the title compounds exhibited good insecticidal activity against Aphis craccivora Koch, Plutella xylostella, Mythimna Separate, and Tetranychus cinnabarinus.

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Section: Introductionmentioning

confidence: 95%

Synthesis and Biological Activity of Some New 6‐perfluoropropanyl Quinoline Derivatives

Zhang

et al. 2018

Journal of Heterocyclic Chem

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“…In our previous work, many heterocyclic derivatives were synthesized and their pesticidal activity was explored, in particular, the pyrazole ring with insecticidal, fungicidal, and nematocidal activity . The three types of pyrazole compounds were designed by extending the carbon chain between the acyl amide group and the benzene ring to discover highly active fungicidal lead compounds (Fig.…”

Section: Introductionmentioning

confidence: 99%

Novel 4‐pyrazole carboxamide derivatives containing flexible chain motif: design, synthesis and antifungal activity

Liu

Zhai

et al. 2019

Pest Management Science

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Background In recent years, carboxamide fungicides, targeting succinate dehydrogenase (SDH), have shown highly efficient and broad spectrum fungicidal activity. Structure–activity relationship (SAR) results for these commercial fungicides show that the carboxamide group was a key active group. This is useful information for the discovery of new pyrazole carboxamide derivatives with fungicidal activity. Results Twenty‐seven novel pyrazole carboxamides were designed and synthesized. Their fungicidal activities against Gibberella zeae, Phytophthora infestans, Phytophthora capsici, Rhizoctonia solani, Alternaria solani, Botrytis cinerea, Fusarium oxysporum, Cercospora arachidicola, Sclerotinia sclerotiorum and Physalospora piricola were tested; derivatives possessed excellent inhibitory at 50 mg L−1 in particular. Furthermore, some pyrazole carboxamides exhibited remarkably high activities against Sclerotinia sclerotiorum in vitro with EC50 values of 2.04 to 15.2 μg mL−1. In addition, some compounds also exhibited high activities against Physalospora piricola, Cercospora arachidicola and Phytophthora capsici. Inhibition activities against SDH proved that the designed analogues were effective at the enzyme level. The SAR of these pyrazole carboxamides was studied by using the docking method. Conclusion It is possible that pyrazole carboxamides, which exhibit good activity against Sclerotinia sclerotiorum, can be further optimized as a lead compounds of carboxamide fungicides. © 2019 Society of Chemical Industry

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“…In recent reference, her group 17 built a modelling of the P. capsici cellulose synthase 3. In our previous work [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] , many bioactive compounds were designed and synthesised. In this paper, based on the structure of seven commercialised CAA fungicides, we found that they have similar structural fragments: amide bond, para-substituted phenyl, 3,4-dialkyloxy substituted phenyl.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model

Peng

Zhao

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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2020) Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model, Journal of Enzyme Inhibition and Medicinal Chemistry, 35:1, 682-691, ABSTRACTThirty-six novel threoninamide carbamate derivatives were designed and synthesised using active fragment-based pharmacophore model. Antifungal activities of these compounds were tested against Oomycete fungi Phytophthora capsici in vitro and in vivo. Interestingly, compound I-1, I-2, I-3, I-6 and I-7 exhibited moderate control effect (>50%) against Pseudoperonospora cubensis in greenhouse at 6.25 lg/ mL, which is better than that of control. Meanwhile most of these compounds exhibited significant inhibitory against P. capsici. The other nine fungi were also tested. More importantly, some compounds exhibited remarkably high activities against Sclerotinia sclerotiorum, P. piricola and R. solan in vitro with EC 50 values of 3.74-9.76 lg/mL. It is possible that the model is reliabile and this method can be used to discover lead compounds for the development of fungicides. ARTICLE HISTORY

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Synthesis and in vivo fungicidal activity of some new quinoline derivatives against rice blast

Cited by 52 publications

References 24 publications

Synthesis and Biological Activity of Some New 6‐perfluoropropanyl Quinoline Derivatives

Synthesis and Biological Activity of Some New 6‐perfluoropropanyl Quinoline Derivatives

Novel 4‐pyrazole carboxamide derivatives containing flexible chain motif: design, synthesis and antifungal activity

Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model

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