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

The synthesis, characterization and activity test of two potential herbicide safeners of dichloroacetyl oxazolidine were described in this paper. Two compounds were synthesized in this paper:Ⅰ: N-dichloroacetyl-2,3-dimethyl-1-oxa-4-aza-spiro-4.5-decane;Ⅱ: N-dichloroacetyl-3-methyl-2-ethyl -1-oxa-4-aza-spiro-4.5-decane.Some materials were synthesized in this paper.At first, 3-nitro-2-butanol and 2-nitro-3- pentanol were synthesized with nitroethane and acetaldehyde or nitroethane and propionaldehyde , the yield were 51.96% and 64.86%; 3-nitro-2-butanol and 2-nitro-3- pentanol were reduced to 3- amino -2-butanol and 2-amino-3- pentanol with iron, and the yield were 74.13% and 80.58%. Two compounds were synthesized with two methods. The two compounds can be synthesized by two steps with triethylamine as catalyst. After the water produced in the synthesis of oxazolidine was removed with different solvents by water segregator, triethylamine was added and dichloroacetyl chloride was dropped. The optimum experimental conditions of the compoundⅠwere as follows: benzene was solvent, temperature was -5~0℃ and stirring time was 3hr,the yield was 90.78%; compoundⅡ: benzene was solvent, temperature was 0～5℃ and stirring time was 3hr, the yield was 86.76%.When hydroxide sodium acted as catalyst, dichloroacetyl chloride was directly dropped into the system after the intermediate product was synthesized by the condensation of aminoalcohols and cyclohexanone. The optimum experimental conditions of the compoundⅠwere as follows: toluene acted as solvent, temperature was 0~5℃ and stirring time was 3hr,the yield was 72.89%; compoundⅡ: toluene acted as solvent, temperature was -5~0℃ and stirring time was 3hr,the yield was 69.11%. The structures of compoundⅠandⅡwere confirmed by TLC, UV, IR, 1HNMR and elementary analysis. The effect of two compounds on the detoxification of acetochlor and chlorsulfuron in soil was determined by testing plant height, fresh weight and GSH content of maize. Two compounds can protect maize from being injuried by acetochlor and chlorsulfuron. In addition, the effect of two compounds and AD-67 on the detoxification of acetochlor and chlorsuluron in soil was compared. When concentration of three compounds was 50 mg/kg, compoundⅠwas better than compoundⅡ in protecting maize from being injuried by acetochlor. When the concentration of acetochlor was 60mg/kg, the detoxification of AD67 was the best one. The effect of compound Ⅱ on the detoxification of chlorsulfuron in soil was better than compoundⅠ. When the concentration of chlorsuluron was 1μg/kg,2μg/kg ,4μg/kg, the detoxification effect of AD-67 was the best.Candidate: Li Yingjiao Major: PesticidesSupervisor: Prof. Ye Fei...