Design, synthesis and biological evaluation of 1H-pyrazole-5-carboxamide derivatives as potential fungicidal and insecticidal agents

Huang, Danling; Huang, Mingzhi; Liu, Weidong; Liu, Aiping; Liu, Xing‐Ping; Chen, Xiaoyang; Hui, Pei; Sun, Jiong; Yin, Dulin; Wang, Xiaoguang

doi:10.1007/s11696-017-0198-4

Cited by 10 publications

(9 citation statements)

References 12 publications

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“…The synthetic routes of all target compounds and intermediates are shown in Figure 3. [ 26,31–33 ] The structures of all synthesized compounds were characterized by NMR, MS, and elemental analysis. The chemical structures, MS data, physical properties, and biological activities of all target compounds 12a ‐ l are illustrated in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…The bioactivity tests of the target compounds were conducted according to our previous studies. [ 26,34‐38 ] Stock solution of 1.0 g/L for every test compound was prepared in DMF and then diluted to the required test concentrations (50‐500 mg/L) with water containing Tween 80 (0.4 mg/L).…”

Section: Methodsmentioning

confidence: 99%

“…In our previous studies, [ 23–26 ] we discovered that compounds containing 2‐phenylthiazole or oxazole motifs ( Ia ‐ Ie , Figure 2) showed excellent bioactivities. Besides the ones we have discovered, thiazole or oxazole are also commonly used in a variety of approved agrochemicals (eg, dicloromezotiaz, thiamethoxam, and oxathiapiprolin) and medicines (eg, acotiamide, isavuconazole, and tivozanib).…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis, and bioactivities of novel pyridazinone derivatives containing 2‐phenylthiazole or oxazole skeletons

Dang

Liu

Huang

et al. 2020

Journal of Heterocyclic Chem

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A series of novel pyridazinone derivatives were designed and synthesized by replacing 4‐(tert‐butyl)phenyl moiety of pyridaben with 2‐phenylthiazole or oxazole fragments via activity substructure connecting approach. The structures of all target compounds were characterized through NMR, MS, and elemental analysis. Bioassay results exhibit that most compounds showed potent bioactivities against Aphis fabae, Tetranychus urticae, Erysiphe graminis, and/or Puccinia polysora. Among the newly synthesized compounds, 2‐(tert‐butyl)‐4‐chloro‐5‐(((2‐phenylthiazol‐4‐yl)methyl)thio)pyridazin‐3(2H)‐one (12b) displays remarkable insecticidal activity against A fabae. Its LC50 value (2.73 mg/L) is better than that of pyridaben (5.46 mg/L), although inferior to that of imidacloprid (0.51 mg/L). In addition to its extraordinary insecticidal activity, compound 12b also exerts 96.9% fungicidal activities against P polysora at 500 mg/L in vivo, significantly superior to that of pyridaben (50.0%), while slightly lower than that of tebuconazole (100%). This article discusses the synthesis, bioassay results, and structure‐activity relationship of this series of novel pyridazinone derivatives.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Design, synthesis, and bioactivities of novel pyridazinone derivatives containing 2‐phenylthiazole or oxazole skeletons

Dang

Liu

Huang

et al. 2020

Journal of Heterocyclic Chem

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“…Stock solution of every test compound was prepared in DMF at a concentration of 1000 mg /L and then the solution was diluted to the required test concentration (50-500 mg/L) with water containing Tween 80 (0.40 mg/L) [14][15][16][17].…”

Section: Biological Assaymentioning

confidence: 99%

Synthesis and fungicidal activity of novel imidazo[4, 5-b]pyridine derivatives

Liu

et al. 2019

Heterocyclic Communications

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A series of novel imidazo[4,5-b]pyridine derivatives were synthesized and their structures were characterized by NMR spectroscopy, mass spectrometry and elemental analysis. The results of bioassays showed that some compounds exhibit good fungicidal activity against Puccinia polysora In particular, compound 7b showed an EC50 value of 4.00 mg/L, which was comparable with that of tebuconazole. Besides, preliminary structure-activity relationship was discussed.

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“…Therefore, it is necessary to develop highly efficient and environmentally friendly bactericides to protect crops. Thiazole-containing aromatic heterocycles are reported to bind to certain proteins and receptors of bacteria and exhibit a wide range of biological activities such as insecticidal [4,5], bactericidal [6][7][8], herbicidal [9], antiviral [10] and fungicidal ones [11,12]. In addition, compounds with an amide structure have revealed various activities as antimicrobial [13][14][15] and nematicidal [16,17] agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Evaluation of N-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties

Zhou

Wang

et al. 2020

Molecules

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A series of new N-phenylacetamide derivatives containing 4-arylthiazole moieties was designed and synthesized by introducing the thiazole moiety into the amide scaffold. The structures of the target compounds were confirmed by 1H-NMR, 13C-NMR and HRMS. Their in vitro antibacterial activities were evaluated against three kinds of bacteria—Xanthomonas oryzae pv. Oryzae (Xoo), Xanthomonas axonopodis pv. Citri (Xac) and X.oryzae pv. oryzicola (Xoc)—showing promising results. The minimum 50% effective concentration (EC50) value of N-(4-((4-(4-fluoro-phenyl)thiazol-2-yl)amino)phenyl)acetamide (A1) is 156.7 µM, which is superior to bismerthiazol (230.5 µM) and thiodiazole copper (545.2 µM). A scanning electron microscopy (SEM) investigation has confirmed that compound A1 could cause cell membrane rupture of Xoo. In addition, the nematicidal activity of the compounds against Meloidogyne incognita (M. incognita) was also tested, and compound A23 displayed excellent nematicidal activity, with mortality of 100% and 53.2% at 500 μg/mL and 100 μg/mL after 24 h of treatment, respectively. The preliminary structure-activity relationship (SAR) studies of these compounds are also briefly described. These results demonstrated that phenylacetamide derivatives may be considered as potential leads in the design of antibacterial agents.

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Design, synthesis and biological evaluation of 1H-pyrazole-5-carboxamide derivatives as potential fungicidal and insecticidal agents

Cited by 10 publications

References 12 publications

Design, synthesis, and bioactivities of novel pyridazinone derivatives containing 2‐phenylthiazole or oxazole skeletons

Design, synthesis, and bioactivities of novel pyridazinone derivatives containing 2‐phenylthiazole or oxazole skeletons

Synthesis and fungicidal activity of novel imidazo[4, 5-b]pyridine derivatives

Synthesis and Antibacterial Evaluation of N-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties

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