Studies On The Synthesis, Characterization And Activity Of One Potential Herbicide Safeners

The synthesis, characterization and activity test of potential herbicide safeners of 5-dichloroacetyl-3,6-dimethyl-3-ethyl-9-oxo-1,5-diazabicyclo[4.3.0] nonane was described in this paper.Some materials were synthesized at first. 2-methyl-2-ethyl-1,3-dinitropropane was synthesized with butanone and nitromethane, the yield was 54.7%; 2-methyl-2-ethyl-1,3-dinitropropane was reduced to 2-methyl-2-ethyl-1,3-propanediamine with iron, the yield was 81.2%; the intermediate product 3,6-dimethyl-3-ethyl-9-oxo-1,5-diaz-abicyclo[4.3.0] nonane was synthesized with 2-methyl-2-ethyl-1,3-propanediamine and levulinic acid ,the yield was 82.5%.5-dichloroacetyl-3,6-dimethyl-3-ethyl-9-oxo-1,5-diazabicyclo[4.3.0] nonane was synthesized with two methods. In the first method, the raw materials were 2-methyl-2-ethyl-1,3-propanediamine and levulinic acid. When the catalyst was triethylamine, the optimum experimental conditions of the product were as following: methylbenzene acted as solvent, the mixture ratio was 1:1, temperature was 35~40℃ and stirring time was 1h., the yield was 79.8%; When hydroxide sodium acted as catalyst, the optimum experimental conditions were as following: methylbenzene acted as solvent, the mixture ratio was 1:1, temperature was 45~50℃ and stirring time 1h., the yield was 81.4%. In the second method, 3,6-dimethyl-3-ethyl-9-oxo-1,5-diazabicyclo[4.3.0] nonane acted as raw material. When the catalyst was triethylamine, the optimum experimental conditions of the product were as following: methylbenzene acted as solvent, temperature was 25~30℃ and stirring time was 2h., the yield was 61.7%; When hydroxide sodium acted as catalyst, the optimum experimental conditions were as following: benzene was solvent, temperature was 35~40℃ and stirring time was 1h., the yield was 63.8%.The structures of the intermediate product and end product were confirmed by TLC, UV, IR, 1HNMR and elementary analysis. The influence of the product on the toxicity of chlorsulfuron and imazethapyr in soil was determined by testing plant height, fresh weight and GSH content of maize. The product can protect maize from injury of chlorsulfuron and imazethapyr. In addition, the effect of the product and BAS-145138 on the toxicity of chlorsulfuron and imazethapyr in soil was compared. When concentration of two compounds was 5 mg/kg, in the soil of chlorsulfuron residue, the protecting effect of BAS-145138 was better ; In the soil of imazethapyr residue, the protecting effect was not different if the concentration of imazethapyr was low, the effect of BAS-145138 was better if the imazethapyr was high. Candidate: Sun Taifan Speciality: Pesticides Supervisor: Prof.Ye Fei...