Synthetic And Biological Activity Of 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone Derivatives

Since oxime-ether compounds are characterized by active biological traits, they are particularly valuable for medical research and widely applied in pesticides as well.Presently, the production of pesticides focuses on the molecular design and synthesis of these compounds as well as the study on their biological activity. Oxime- ether compounds possess not only good environmental compatibility, but also high activity for downy mildew fungi, Culex pipiens and Musca domestica, as a result, they are mainly used for pesticide insecticidal, fungicidal and herbicidal.Cyproconazole, a triazole fungicide, is marked by high efficiency,broad-spectrum, and absorption characteristic; meanwhile, it functions as a plant growth regulator. Therefore, it is widely used in pesticides as a preventive against and a treatment for plant common pathogens.Taking 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone as the raw material for epoxidation reaction, the reaction with 1,2,4-1H-triazoleto gets cyproconazole. Then,the cyproconazole is used for the separation of the diastereomer by liquid chromatography on the chiral resolution. The yield of the epoxidation reaction has reached 91.6% with a 91.6% content while the yield of the cyproconazole synthesis reaction has reached 75.5% with a 95.5% content.Taking the intermediate of cyproconazole 1-(4-chlorophenyl)-2-cyclopropyl-1-acetone as raw materials,1-(4-chlorophenyl)-2-cyclopropylpropan-1-one oxime was prepared by oximation reaction. Then,10 kinds of 1-(4-chlorophenyl)-2-cyclopropylpropan-1-one oxime have been prepared by etherification reaction with potassium iodide and TBAB as catalyst.The reaction conditions of oximation and etherification are stable, with little side reactions, and the following chemical treatment and operation are simple, with short reaction time and high yield. In addition, the yield of oximation product has reached 96%, and the yield of the etherification reaction is38.6% ~80.3%. The structure of the target products has been analyzed by 1H NMR.The influence on each reaction step has been examined by process parameters including the proportioning of materials, the mode of feeding materials, reaction temperature, reaction time, catalyst, amount of solvent. Optimum process has been acquired, and primary mechanisms of every reaction have also been discussed.