Synthesis and fungicidal activity of novel 1,2,4-triazole derivatives containing a pyrimidine moiety

References

• Madhu, S.-M.; Nagarjuna, U.; Padmavathi, V.; Padmaja, A.; Vasudeva, R.-N.; Vijaya, T. Synthesis and Antimicrobial Activity of Pyrimidinyl 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles and 1,2,4-Triazoles. Eur. J. Med. Chem. 2018, 145, 1–10. DOI:10.1016/j.ejmech.2017.12.067.
   PubMed Web of Science ®Google Scholar
• Chen, M.-H.; Chen, L.-J.; Zhu, X.-S.; Wang, X.-B.; Li, Q.; Zhang, J.-P.; Lu, D.-W.; Xue, W. Synthesis and Biological Activities of Cyclanone O-(2-(3-Aryl-4- Amino-4H-1,2,4-Triazol-3-yl) Thio)Acetyl)Oxime Derivatives. Phosphorus Sulfur Silicon Relat. Elem. 2017, 192, 1259–1263. DOI:10.1080/10426507.2017.1315419.
   Web of Science ®Google Scholar
• Jin, R.; Liu, J.; Zhang, G.; Li, J.; Zhang, S.; Guo, H. Design, Synthesis, and Antifungal Activities of Novel 1,2,4-Triazole Schiff Base Derivatives. Chem. Biodivers. 2018, 5, e1800263. DOI:10.1002/cbdv.201800263.
   Google Scholar
• Jia, C.-Q.; Su, W.-C.; Xu, Y.-J.; Liu, J.-P.; Qin, Z.-H. Synthesis, Structure Characterization and Fungicidal Activity of 1,3-Disubstituted-1H-1,2,4-Triazole-5-Amines. Chin. J. Org. Chem. 2016, 36, 830–837. DOI:10.6023/cjoc201510021.
   Web of Science ®Google Scholar
• El-Sayed, H.-A.; Moustafa, A.-H.; Haikal, A. –E.-Z. Synthesis, Antiviral and Antimicrobial Activity of 1,2,4-Triazole Thioglycoside Derivatives. Phosphorus Sulfur Silicon Relat. Elem. 2013, 188, 649–662. DOI:10.1080/10426507.2012.668990.
   Web of Science ®Google Scholar
• Tariq, S.; Alam, O.; Amir, M. Synthesis, anti-Inflammatory, P38α MAP Kinase Inhibitory Activities and Molecular Docking Studies of Quinoxaline Derivatives Containing Triazole Moiety. Bioorg. Chem. 2018, 76, 343–358. DOI:10.1016/j.bioorg.2017.12.003.
   PubMed Web of Science ®Google Scholar
• Ganesh Kumar, T. –N.-V.; Gautham Shenoy, G.; Kar, S.-S.; Shenoy, V.; Bairy, I. Design, Synthesis and Evaluation of Antitubercular Activity of Novel 1,2,4-Triazoles against MDR Strain of Mycobacterium Tuberculosis. Pharm. Chem. J. 2018, 51, 907–917. DOI:10.1007/s11094-018-1714-8.
   Web of Science ®Google Scholar
• Kaldrikyan, M.-A.; Melik-Ohanjanyan, R.-G.; Arsenyan, F.-H. Synthesis and Antitumor Activity of 2-N-,3-S-Substituted 5-(4-Benzyloxyphenyl)-1,2,4-Triazoles. Pharm. Chem. J. 2017, 51, 760–763. DOI:10.1007/s11094-017-1688-y.
   Web of Science ®Google Scholar
• Du, H.-F.; Zhi, J.; Yang, L.; Bao, X.-P. Synthesis and Antimicrobial Activities of Novel 1,2,4-Triazole-Acylhydrazone Derivatives Containing the Quinazolin-4-One Moiety. Chin. J. Org. Chem. 2018, 38, 531–538. DOI:10.6023/cjoc201708051.
   Web of Science ®Google Scholar
• Zhang, Y.; Wang, B.-L.; Zhan, Y.-Z.; Zhang, L.-Y.; Li, Y.-H.; Li, Z.-M. Synthesis and Biological Activities of Novel 5-(Pyridine-3-yl)-1,2,4-Triazole Mannich Bases and Bis-Mannich Bases Containing Piperazine Moiety. Chem. J. Chin. U. 2016, 37, 1100–1107. DOI: 10.7503/cjcu20160042.
   Web of Science ®Google Scholar
• Liu, X.-H.; Wang, Q.; Sun, Z.-H.; Wedge, D. E.; Becnel, J. J.; Estep, A. S.; Tan, C.-X.; Weng, J.-Q. Synthesis and Insecticidal Activity of Novel Pyrimidine Derivatives Containing Urea Pharmacophore against Aedes Aegypti. Pest Manag. Sci. 2017, 73, 953–959. DOI:10.1002/ps.4370.
   PubMed Web of Science ®Google Scholar
• Chen, Q.; Zhu, X.-L.; Jiang, L.-L.; Liu, Z.-M.; Yang, G.-F. Synthesis, Antifungal Activity and CoMFA Analysis of Novel 1,2,4-Triazolo[1,5-a]Pyrimidine Derivatives. Eur. J. Med. Chem. 2008, 43, 595–603. DOI:10.1016/j.ejmech.2007.04.021.
   PubMed Web of Science ®Google Scholar
• Zhang, J.; Peng, J.-F.; Bai, Y.-B.; Wang, P.; Wang, T.; Gao, J.-M.; Zhang, Z.-T. Synthesis of Pyrazolo[1,5-a]Pyrimidine Perivatives and Their Antifungal Activities against Phytopathogenic Fungi in Vitro. Mol. Divers. 2016, 20, 887–896. DOI:10.1007/s11030-016-9690-y.
   PubMed Web of Science ®Google Scholar
• Li, K.-J.; Qu, R.-Y.; Liu, Y.-C.; Yang, J.-F.; Devendar, P.; Chen, Q.; Niu, C.-W.; Xi, Z.; Yang, G.-F. Design, Synthesis, and Herbicidal Activity of Pyrimidine–Biphenyl Hybrids as Novel Acetohydroxyacid Synthase Inhibitors. J. Agric. Food Chem. 2018, 66, 3773–3782. DOI:10.1021/acs.jafc.8b00665.
   PubMed Web of Science ®Google Scholar
• Cheng, X.; Wang, S.; Cui, D.; Li, B. The Synthesis and Herbicidal Activity of 5-(Substituted-Phenyl)-4,6-Dioxo-4,5,6,7-Tetrahydropyrazolo(3,4-d)Pyrimidines. J. Heterocyclic Chem. 2015, 52, 607–610. DOI:10.1002/jhet.2047.
   Web of Science ®Google Scholar
• Wang, Y.-Y.; Xu, F.-Z.; Zhu, Y.-Y.; Song, B.; Luo, D.; Yu, G.; Chen, S.; Xue, W.; Wu, J. Pyrazolo[3,4-d]Pyrimidine Derivatives Containing a Schiff Base Moiety as Potential Antiviral Agents. Bioorg. Med. Chem. Lett. 2018, 28, 2979–2984. DOI:10.1016/j.bmcl.2018.06.049.
   PubMed Web of Science ®Google Scholar
• Xu, X.-J.; Wang, J.; Yao, Q.-Z. Synthesis and Quantitative Structure-Activity Relationship (QSAR) Analysis of Some Novel Oxadiazolo[3,4-d]pyrimidine Nucleosides Derivatives as Antiviral Agents. Bioorg. Med. Chem. Lett. 2015, 25, 241–244. DOI:10.1016/j.bmcl.2014.11.065.
   PubMed Web of Science ®Google Scholar
• Kumar, B.; Sharma, P.; Gupta, V.-P.; Khullar, M.; Singh, S.; Dogra, N.; Kumar, V. Synthesis and Biological Evaluation of Pyrimidine Bridged Combretastatin Derivatives as Potential Anticancer Agents and Mechanistic Studies. Bioorg. Chem. 2018, 78, 130–140. DOI:10.1016/j.bioorg.2018.02.027.
   PubMed Web of Science ®Google Scholar
• El-Miligy, M. M. M.; Hazzaa, A. A.; El-Messmary, H.; Nassra, R. A.; El-Hawash, S. A. M. New Hybrid Molecules Combining Benzothiophene or Benzofuran with Rhodanine as Dual COX-1/2 and 5-LOX Inhibitors: Synthesis, Biological Evaluation and Docking Study. Bioorg. Chem. 2017, 72, 102–115. DOI:10.1016/j.bioorg.2017.03.012.
   PubMed Web of Science ®Google Scholar
• Venkatachalam, S.-R.; Salaskar, A.; Chattopadhyay, A.; Barik, B.; Mishra, B.; Gangabhagirathi, R.; Priyadarsini, K.-I. Synthesis, Pulse Radiolysis, and in Vitro Radioprotection Studies of Melatoninolipoamide, a Novel Conjugate of Melatonin and α-Lipoic Acid. Bioorg. Med. Chem. 2006, 14, 6127–6456. DOI:10.1016/j.bmc.2006.05.042.
   Web of Science ®Google Scholar
• Zhao, L.; Ma, X.-D.; Chen, F.-E. Development of Two Scalable Syntheses of 4-Amino-5-Aminomethyl-2-Methylpyrimidine: Key Intermediate for Vitamin B1. Org. Process Res. Dev. 2012, 16, 57–60. DOI:10.1021/op2002003.
   Web of Science ®Google Scholar
• Donald, P.; Everette, L.-M.; Frank, D.-P. Studies on Pyrimidines Related to Nitamin B1. I. A New Synthesis of 2-Methyl-6-Aminopyrimidine-5-Aldehyde. J. Am. Chem. Soc. 1940, 62, 2818–2820. DOI:10.1021/ja01867a055.
   Google Scholar
• Chattapadhyay, T.-K.; Dureja, P. Antifungal Activity of 4-Methyl-6-Alkyl-2H-Pyran-2-Ones. J. Agric. Food Chem. 2006, 54, 2129–−2133. DOI:10.1021/jf052792s.
   PubMed Web of Science ®Google Scholar
• Xu, W.-M.; He, J.; He, M.; Han, F.-F.; Chen, X.-H.; Pan, Z.-X.; Wang, J.; Tong, M.-G. Synthesis and Antifungal Activity of Novel Sulfone Derivatives Containing 1,3,4-Oxadiazole Moieties. Molecules 2011, 16, 9129–9141. DOI:10.3390/molecules16119129.
   PubMed Web of Science ®Google Scholar
• Xu, W.-M.; Yang, S.; Bhadury, P.; He, J.; He, M.; Gao, L.-L.; Hu, D.-Y.; Song, B-A. Synthesis and Bioactivity of Novel Sulfone Derivatives Containing 2,4-Dichlorophenyl Substituted 1,3,4-Oxadiazole/Thiadiazole Moiety as Chitinase Inhibitors. Pestic. Biochem. Phys. 2011, 101, 6–15. DOI:10.1016/j.pestbp.2011.05.006.
   Web of Science ®Google Scholar
• Fan, Z.-J.; Shi, J.; Bao, X.-P. Synthesis and Antimicrobial Evaluation of Novel 1,2,4-Triazole Thioether Derivatives Bearing a Quinazoline Moiety. Mol. Divers. 2018, 22, 657–667. DOI:10.1007/s11030-018-9821-8.
   PubMed Web of Science ®Google Scholar
• Xu, M.; Zhu, Y.-B.; Wang, M.; Khan, I. A.; Liu, X.-H.; Weng, J.-Q. Microwave-Assisted Synthesis and Antifungal Activity of Novel 1,2,4- Triazole Thioether Derivatives Containing Pyrimidine Moiety. Lett. Drug Des. Discov. 2018, 15, 347–352. DOI:10.2174/1570180814666170602082440.
   Web of Science ®Google Scholar
• Wu, W.-N.; Chen, Q.; Tai, A.-Q.; Jiang, G.-Q.; Ouyang, G.-P. Synthesis and Antiviral Activity of 2-Substituted Methlthio-5-(4-Amino-2-Methylpyrimidin-5-yl)-1,3,4-Oxadiazole Derivatives. Bioorg. Med. Chem. Lett. 2015, 25, 2243–2246. DOI:10.1016/j.bmcl.2015.02.069.
   PubMed Web of Science ®Google Scholar