Novel trifluoromethylpyrazole acyl urea derivatives: Synthesis, crystal structure, fungicidal activity and docking study

Wang, Han; Zhai, Zhi-Wen; Shi, Yanhong; Tan, Cheng‐Xia; Weng, Jian‐Quan; Li, Han; Li, Baoju; Liu, Xinghai

doi:10.1016/j.molstruc.2018.06.050

Cited by 38 publications

(26 citation statements)

References 33 publications

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“…A suitable single crystal (CCDC 1887856) of compound 12b for X‐ray diffraction was obtained by recrystallizing with ethyl acetate. Adopting known procedures, the crystal structure resolution was compiled from the collected diffraction data.…”

Section: Methodsmentioning

confidence: 99%

One‐pot synthesis, structure and structure–activity relationship of novel bioactive diphenyl/diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(arylamino)methylphosphonates

Wang

Zhu

et al. 2019

Pest Management Science

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BACKGROUND N‐Pyridylpyrazole derivatives have received continuous attention in agrochemical research during the last decade owing to their remarkable insecticidal or fungicidal potentials. To look for novel heterocyclic agrochemicals for increasing production of agriculture, a series of novel α‐aminophosphonate derivatives containing N‐pyridylpyrazole moiety were synthesized. RESULTS The structures of the title compounds were confirmed via melting point, IR, 1H NMR, 13C NMR, 31P NMR, HRMS and elemental analysis. The single crystal structure of diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(2,6‐dimethylphenylamino)methylphosphonate (compound 12b) was first reported. Moreover, the bioassays displayed that the title compounds exhibited modest or weak insecticidal activities against oriental armyworm at 200 μg mL−1. The first investigation on the fungicidal potential of chlorantraniliprole showed no significant activities towards the six tested fungi found in this study, however, most of the title compounds displayed apparent in vitro fungicidal activity against some plant fungi, in particular excellent activities towards Physalospora piricola. Compounds 11a and 11b had EC50 values of 18.8 and 17.4 μg mL−1, respectively, which were comparable with that of fungicide control triadimefon (EC50 = 24.7 μg mL−1) against Physalospora piricola. In addition, some compounds exhibited modest in vivo control efficacy at 0.5 mg mL−1 towards Sclerotinia sclerotiorum (11b: 30.1(±1.8)%), Rhizoctonia cerealis (11a: 20.4(±2.1)%; 11b: 30.2(±2.2)%), and Erysiphe graminis (11a: 30.3(±1.8)%; 12d: 40.2(±0.9)%). CONCLUSION Compounds 11a, 11b and 12d could be promising new lead structures for the development and discovery of novel fungicides towards Physalospora piricola and Erysiphe graminis. The structure‐activity relationship (SAR) analysis provided useful guidance and new understanding for the design of novel pyridylpyrazole‐containing agrochemicals. © 2019 Society of Chemical Industry

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Section: Methodsmentioning

confidence: 99%

One‐pot synthesis, structure and structure–activity relationship of novel bioactive diphenyl/diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(arylamino)methylphosphonates

Wang

Zhu

et al. 2019

Pest Management Science

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“…Docking scores (‐CDOCKER interaction energy) of the best‐fitted poses with the active site at the SDH structure were then recorded. The entire process was done in accordance with our previous work …”

Section: Fungicidal Activitymentioning

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 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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Novel trifluoromethylpyrazole acyl urea derivatives: Synthesis, crystal structure, fungicidal activity and docking study

Cited by 38 publications

References 33 publications

One‐pot synthesis, structure and structure–activity relationship of novel bioactive diphenyl/diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(arylamino)methylphosphonates

One‐pot synthesis, structure and structure–activity relationship of novel bioactive diphenyl/diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(arylamino)methylphosphonates

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

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

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