Synthesis of novel N-pyridylpyrazole derivatives containing 1,2,4-oxadiazole moiety via 1,3-dipolar cycloaddition and their structures and biological activities |
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| Institution: | 1. Yaroslavl State Technical University, 88 Moscowsky Pr, 150023 Yaroslavl, Russian Federation;2. Pharmaceutical Technology Transfer Center, Ushinsky Yaroslavl State Pedagogical University, 108 Respublikanskaya St., Yaroslavl 150000, Russian Federation;3. Organic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation;1. Institute of Chemistry, Saint Petersburg State University, 26 Universitetsky Pr, Peterhof, Saint Petersburg 198504, Russian Federation;2. M.V. Lomonosov Institute of Fine Chemical Technologies, MIREA – Russian Technological University, 86 Vernadskogo Pr, Moscow 119571, Russian Federation;3. Pharmaceutical Technology Transfer Centre, Ushinsky Yaroslavl State Pedagogical University, 108 Respublikanskaya St., Yaroslavl 150000, Russian Federation;1. Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Buenos Aires, Argentina;2. BioLab, Instituto Universitario de Bio-Orgánica “Antonio González” (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, 38206 La Laguna, Spain;3. CONICET – Universidad de Buenos Aires, Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), Buenos Aires, Argentina;1. Division of Molecular Entomology, ICAR-National Bureau of Agricultural Insect Resources, Bengaluru 560 024, Karnataka, India;2. Centre for Agricultural Bioinformatics, Indian Agricultural Statistical Research Institute, Pusa, New Delhi 110 012, India |
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| Abstract: | A series of novel 1,2,4-oxadiazole-containing N-pyridylpyrazole derivatives 12a−h were efficiently synthesized with pivaldehyde, pyridylpyrazole carboxylic acid and arylamine as raw materials via 1,3-dipolar cycloaddition. Their structures were identified by melting points, 1H NMR, 13C NMR and elemental analysis or HRMS. The exploration on the single-crystal structures of 12c and 12g revealed the stereochemical and substituent oriental characteristics, and the relevance of the structure and the reaction activity of this type of compounds. The preliminary bioassays indicated that several compounds had good insecticidal activities, among which 12c showed a lethality rate of 80% towards Mythimna separata Walker at 200 μg/mL; some of the compounds exhibited favorable fungicidal activities at 50 μg/mL against Physalospora piricola, Rhizoctonia cereal, Sclerotinia sclerotiorum, etc. Among which, 12a, 12b, 12c and 12h could be considered as new fungicidal leading compounds for further structural optimization. These discoveries along with the structure-activity relationship analysis in this paper will provide useful guidance for the innovative studies on new pyridylpyrazole derivatives and their applications in agrochemical area. |
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| Keywords: | 1 2 4-Oxadiazole 1 3-Dipolar cycloaddition Insecticidal activity Fungicidal activity Structure-activity relationship |
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