Design,synthesis and fungicidal activity evaluation of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety |
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| Affiliation: | 1. College of Chemistry and Chemical Engineering, Hunan University, No. 1 Lushan Road(s), Changsha 410082, Hunan Province, People’s Republic of China;2. National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry, Changsha 410007, Hunan Province, People’s Republic of China;3. Hunan Province Key Laboratory for Agrochemicals, Changsha 410014, People’s Republic of China;4. Schooll of Medicine, Hunan University of Chinese Medicine, Changsha 410208, People’s Republic of China;1. Department of Pharmaceutical Organic Chemistry, College of Pharmacy, Al-Azhar University, Cairo, 11884, Egypt;2. Department of Comparative Pathobiology, College of Veterinary Medicine, Purdue University, West Lafayette, IN, 47907, USA;3. Purdue Institute of Inflammation, Immunology, and Infectious Disease, West Lafayette, IN, 47907, USA;4. University of Science and Technology, Nanoscience Program, Zewail City of Science and Technology, October Gardens, 6th of October, Giza, 12578, Egypt;1. Department of Chemistry, Faculty of Science and Arts, King Khalid University, Mohail, Assir, Saudi Arabia;2. Department of Chemistry, Faculty of Science, Al-Azhar University, 11884 Nasr City, Cairo, Egypt;3. Department of Botany and Microbiology, Faculty of Science, Al-Azhar University, Nasr City, Cairo 11884, Egypt;4. Department of Chemistry, Faculty of Science, King Khalid University, Abha, Saudi Arabia;5. Department of Chemistry, Faculty of Education, Ain Shams University, Egypt;1. Department of Pharmaceutical Organic Chemistry, College of Pharmacy, Al-Azhar University, Cairo 11884, Egypt;2. Department of Comparative Pathobiology, Purdue University, College of Veterinary Medicine, West Lafayette, IN, USA;3. Department of Pharmacology, College of Pharmacy, Al-Azhar University, Cairo 11884, Egypt;4. Purdue Institute for Inflammation, Immunology, and Infectious Diseases, West Lafayette, IN, USA;5. Biomedical Sciences, University of Science and Technology, Zewail City of Science and Technology, Giza, Egypt;1. Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil;2. Departamento de Microbiologia, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil;3. Departamento de Fisiologia e Biofísica, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil;4. Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil;1. Research Center of Analysis and Measurement, Fudan University, Shanghai 200433, China;2. Technical Center for Industrial Product and Raw Material Inspection and Testing of SHCIQ, Shanghai 200135, China;3. State Key Laboratory Breeding Base of Systematic Research Development and Utilization of Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu, Sichuan 611137, China |
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| Abstract: | Diflumetorim is a member of pyrimidinamine fungicides that possess excellent antifungal activities. Nevertheless, as reported that the activity of diflumetorim to corn rust (Puccinia sorghi) was not ideal (EC50 = 53.26 mg/L). Herein, a series of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety were designed based on our previous study and the structural characteristics of diflumetorim, synthesized and bioassayed to discover novel fungicides with excellent antifungal activities. Among these compounds, T18 gave the optimal fungicidal activity, which respectively offers control effects with EC50 values of 0.93 mg/L against P. sorghi and 1.24 mg/L against E. graminis, significantly superior to commercial fungicides diflumetorim, tebuconazole, and flusilazole. Cell cytotoxicity results suggested that compound T18 has lower toxicities than diflumetorim. Furthermore, DFT calculation indicated that the phenyl-thiazole/oxazole moiety plays an unarguable role in the improvement of activity, which will contribute to designing and developing more potent compounds in the future. |
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| Keywords: | Diflumetorim Pyrimidinamine Antifungal activities DFT calculation |
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