Study On The Design, Synthesis And Biological Activity Of Pyrimidine-5-carboxylic Formic Acid Esters

Pesticides, which are strategic materials in protecting agricultural production, play an irreplaceable role in agriculture modernization process. In the 21st century, environmental protection and sustainable development are the themes that the world advocated, and therefore, this situation requires pesticides industry must continue to develop environmentally friendly ultra-efficient, safe, and innovative green pesticides to meet the challenge. Among them, the pyrimidine formic acid esters herbicides have played a very important role in the world’s agricultural development. In this paper, based on the method of active substructures unionization and the bases of the previous study in our group,53 compounds containing pyrimidine carbamate structures which have not been reported are rationally designed and synthesized. All of the target compounds were characterized by 1H NMR,13C NMR, IR, MS spectra. What’s more, various herbicidal activitives of the target compounds were tested systematicly which shows that a number of compounds have excellent herbicidal activity and may be valueable in herbicidal applications. In this thesis, the specific contents are as following:1. Providing an overview of the current status and future direction of the development of pesticides industry, and the research progress of pyrimidine formic acid esters herbicides. Othewise, the applications of pyrimidine formic acid esters compounds in the field of pesticides are introduced, and synthetic methods of pyrimidine formic acid esters were briefly described.2. Chlorination of 4-(4-fluorophenyl)-2-hydroxy-6-methyl-pyrimidine-5-formic acid ethyl ester with phosphorus oxychloride gives the corresponding 2-chloro-4-(4-fluorophenyl)-6-methyl-pyrimidine-5-formic acid ethyl ester intermediate which undergoes amination/etherification with substituted amines/phenols to produce 36 target compounds. All these compounds ware characterized systematically by 1H NMR,13C NMR, MS and IR spectra.3. The reactions between 2-chloro-4-(4-methylphenyl)-6-methyl-5-carboxylate and substituted amines/phenols give 23 target compounds, which are characterized systematically by 1H NMR,13C NMR, MS, and IR spectra.4. The herbicidal activitives of all the target compounds were tested with greenhouse indoor plate method and the results show that these compounds can effectively control a variety of broadleaf weeds with a high selectivity. All the target compounds could inhibit, in a certain extent, the growth of roots and stems of the rape and ryegrass which are behalf of dicots and monocots representatively.