Synthesis Of New Herbicides Cyclosulfonone And Its Analogs

The article briefly reviewed 4-hydroxyphenylpyruvate dioxygenase(HPPD)and herbicides that target it,and the property,mechanism and synthesis route of Tembotrioe e were introduced in detail.We found a synthesis route of Tembotrioe that had a bright industrialization value through comparing the merits and demerits of all methods in the literature.In this paper,an inexpensive 3-chloro-2-methylaniline as a starting material,after diazotization,acetylated,hydrogen peroxide oxidation,hypochlorite oxidation,esterification,bromination,nucleophilic reaction,hydrolysis,synthesis of the 2-chloro-3-(2,2,2-trifluoroethoxy)methyl-4-methylsulfonyl benzoic acid.And with reference to the relevant literature for each step of the reaction has been optimized and improved.2-chloro-3-(2,2,2-trifluoroethoxy)-4-methyl-benzoic acid methyl sulfonyl chloride was synthesized,and then acid chloride with 1,3-cyclohexanedione to the ester finally in acetone cyanohydrin obtained catalytic rearrangement indexing ring Tembotrioe.And the synthesis technology of every step was improved by reference to the literature.The new process is more convenient and the yield is higher.The structure of the products was determined by IR,NMR and MS.The purity is determined by HPLC or GC.We designed and prepared Fourteen Tembotrioe analogues,confirmed the structure of all intermediates and target products.