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

The synthesis, characterization and activity test of potential herbicide safeners of dichloroacetyl oxazolidine were described in this paper. Two compounds were synthesized in this paper: I : N-dichloroacetyl-3-ethyl-l-oxa-4-aza-spiro-4.5-decane;II : N-dichloroacetyl-2-n-proply-l-oxa-4-aza-spiro-4.5-decane.Some materials were synthesized in this paper at first, 1-nitro-2-pentanol was synthesized with nitromathane and butyraldehyde and the yield was 70.2%; l-nitro-2-pentanol was reduced to 1 -amino-2- pentanol with iron and the yield was 65.2%.Two compounds were synthesized with two methods. 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 compound I were as follows: toluene acted as solvent, temperature was 5~10 and stirring time was 3hr, the yield was 55.08%; compound II: toluene acted as solvent, temperature was-10-5 and stirring time was 3hr, the yield was 63.38%. The two compounds also 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 compound I were as follows: trichloromethane was solvent, temperature was 5-10 and stirring time was 3hr, the yield was 69.56%; compound II: benzene was solvent, temperature was -3~3 and stirring time was 1hr, the yield was 87.91%.The structures of compound I and II were confirmed by TLC, UV, IR, 'HNMR and elementary analysis.The effect of two compounds on the detoxification of acetochlor and imazethapyr 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 imazethapyr. In addition, the effect of two compounds and AD-67 on the detoxification of acetochlor and imazethapyr in soil was compared. When concentration of three compounds was 50 mg/kg, the protectingeffect was not different if the concentration of acetochlor and imazethapyr was low; the effect of AD-67 was better if the concentration of acetochlor and imazethapyr was high.