Studies On The Synthesis, Characterization And Activity Of Chiral Herbicide Safeners

The synthesis, characterization and activity test of chiral herbicide safeners of dichloroacetyl oxazolidine were described in this paper. Two compounds were synthesized in this paper:Ⅰ: (-)-3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine [(-)-R-29148];Ⅱ: (+)-3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine [(+)-R-29148].Some materials were synthesized in this paper at first. L-(+)-aminopropanol tartrate and D-(-)-aminopropanol tartrate were synthesized with resolving agent L-(+)-tartrate and D-(-)-tartrate. Adopt orthogonal experiment scheme of three factors-three levels, to get the optimum experimental conditions of L-(+)-aminopropanol tartrate were as follows: mixture ratio was 1:1, crystal temperature was 20~25℃and crystal time was 24hr,the yield was 91.4%; The optimum experimental conditions of D-(-)-aminopropanol tartrate were as follows: mixture ratio was 1:1, crystal temperature was -5~0℃and crystal time was 24hr,the yield was 89.8%Deal with L-(+)-aminopropanol tartrate and D-(-)-aminopropanol tartrate to get chiral raw material S-(+)-1-amino-2-propanol and R-(-)-1-amino-2-propanol, the yield were 45.2% and 48.7%.The two compounds can be synthesized with hydroxide sodium as catalyst. When hydroxide sodium acted as catalyst, dichloroacetyl chloride was directly dropped into the system after the intermediate product was synthesized by the condensation of S-(+)-1-amino-2-propanol or R-(-)-1-amino-2-propanol and acetone, the yield was 53.78%,51.32%.The structures of compoundⅠandⅡwere confirmed by melting point, optical rotation, TLC, IR, 1HNMR and elementary analysis.The effect on maize of two compounds and (±)-R-29148 on the detoxification of acetochlor and chlorsuluron in soil was compared. The effect of three compounds on the detoxification of acetochlor and chlorsulfuron in soil was determined by testing plant height, plant fresh weight, root length, root fresh weight and GSH content, ALS activity of maize.In addition, the comparison test of two compounds and safener (±)-R-29148 showed...