Design, Synthesis, Fungicidal Activity and Docking Study of Acyl Urea Derivatives Containing Pyrazole Moiety

Sun, Nabo; Shen, Zhonghua; Zhai, Zhi-Wen; Liu, Han; Weng, Jian‐Quan; Tan, Cheng‐Xia; Liu, Xinghai

doi:10.6023/cjoc201702003

Cited by 10 publications

(11 citation statements)

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“…The key intermediates 1 , 2 , 3 , and 4 were synthesized according to the references . First, the pyrazole ring was synthesized from methyl hydrazine and ethyl acetoacetate.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Nematocidal Activity of N‐Substituted 3‐Methyl‐1H‐pyrazole‐4‐carboxamide Derivatives Against Meloidogyne incognita

Shen

et al. 2018

Journal of Heterocyclic Chem

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A series of novel pyrazole carboxamides were designed and synthesized through multi‐step reactions from ethyl acetoacetate and triethyl orthoformate, and their structures were characterized by Fourier transform infrared, 1H‐NMR, 13C‐NMR, mass spectrometry, and elemental analysis. The preliminary insecticidal activity showed that some of them possessed good insecticidal activities against Meloidogyne incognita.

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“…The key intermediates 1 , 2 , 3 , and 4 were synthesized according to the references . First, the pyrazole ring was synthesized from methyl hydrazine and ethyl acetoacetate.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Nematocidal Activity of N‐Substituted 3‐Methyl‐1H‐pyrazole‐4‐carboxamide Derivatives Against Meloidogyne incognita

Shen

et al. 2018

Journal of Heterocyclic Chem

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“…Gibberella zeae (GZ), Phytophthora infestans (PI), Phytophthora capsici (PC), Sclerotinia sclerotiorum (SS), Rhizoctonia solani (RS), Alternaria solani (AS), Botrytis cinerea (BC), Fusarium oxysporum (FO), Cercospora arachidicola (CA) and Physalospora piricola (PP) were provided by the National Pesticide Engineering Research Centre, Nankai University. The fungicidal activities of all the synthetic compounds were tested in vitro against ten fungi using a mycelia growth inhibition method . Each compound was dissolved in dimethyl sulfoxide(DMSO) to prepare the 50 ppm stock solution.…”

Section: Fungicidal Activitymentioning

confidence: 99%

“…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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“…[4][5][6] Mitochondria complex II (Succinate dehydrogenase, SDH) is an important target for pesticidal discovery. [5][6][7] To date, many small molecules [8][9][10][11][12][13][14][15][16][17][18][19][20] targeting SDH were discovered as fungicides and insecticides. The acrylonitrile group was a key skeleton in the insecticides, especially in acaricides, such as cyenopyrafen, SYP-9625.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, acaricidal activities and docking study of novel acrylonitrile derivatives

Zhong¹,

Kang²,

Tan³

et al. 2020

Arkivoc

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A series of novel acrylonitrile derivatives containing a flexible chain were designed using cyflumetofen as lead compound. They were synthesized via two steps. The structures were confirmed by 1 H NMR, 13 C NMR and HRMS. The title acrylonitrile derivatives exhibited good acaricidal activity against Tetranchus urticae. In particular, 3j possessed excellent activity in the green house, at the same level as the control Cyflumetofen at 4 days or 7 days.

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Design, Synthesis, Fungicidal Activity and Docking Study of Acyl Urea Derivatives Containing Pyrazole Moiety

Cited by 10 publications

References 0 publications

Synthesis and Nematocidal Activity of N‐Substituted 3‐Methyl‐1H‐pyrazole‐4‐carboxamide Derivatives Against Meloidogyne incognita

Synthesis and Nematocidal Activity of N‐Substituted 3‐Methyl‐1H‐pyrazole‐4‐carboxamide Derivatives Against Meloidogyne incognita

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

Synthesis, acaricidal activities and docking study of novel acrylonitrile derivatives

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