Chinese Journal of Organic Chemistry >
Synthesis and Bioactivity of 2-Benzoyl Pyrimidine Derivatives
Received date: 2015-12-18
Revised date: 2015-02-17
Online published: 2015-02-18
Supported by
Project supported by the National Key Technologies R&D Program (No. 2011BAE06B02).
2-Benzoyl pyrimidine as a secondary leading structure is developed by twice optimization of 2-pyrimidinoxy-N- aryl benzylamine. Based on this structure, thirty six 2-benzoyl pyrimidine derivatives have been designed and synthesized. All compounds are determined by 1H NMR, 13C NMR and HRMS. Their interior fungicidal activities show that R1 substituent prefers phenyl or heterocyclic group with 2-halo or 2-alkyl group. When introducing fluoride to 6-position on benzene ring, the fungicidal activity is maintained at a similar level. 4,6-Dimethoxy group on pyrimidine ring was recognized as a best substituent by far. The activity is seriously decreased when methyl group is fixed on 5-position of pyrimidine. Even the fungicidal activities become completely disappeared when the ketone group is reduced to hydroxyl group. Among them, three compounds 2,3-dichloro-N-(2-(4,6-dimethoxypyrimidine-2-carbonyl)phenoxy)-N-methylbenzamide (4AHl), 2,5-dichloro-N-(2-(4,6-dime- thoxypyrimidine-2-carbonyl)phenoxy)-N-methylbenzamide (4AHn) and N-(2-(4,6-dimethoxypyrimidine-2-carbonyl)-3-fluoro- phenoxy)-N,2-dimethylbenzamide (4AFd) exhibit comparable fungicidal activity against cucumber powdery mildew to the reference metrafenone.
Lü Qiang, Lu Xinting, Dai Ming, Liu Shimeng, Zhu Weihong, Du Pa, Lü Long . Synthesis and Bioactivity of 2-Benzoyl Pyrimidine Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(6) : 1260 -1269 . DOI: 10.6023/cjoc201412032
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