【目的】合成N-苯氧苯基取代的α-氨基酸衍生物,并测定化合物的生物活性及其在植物体内的传导性。【方法】通过氨基二苯醚类化合物分别与乙醛酸乙酯和丙酮酸乙酯缩合,形成2个希夫碱化合物(Ia-Ib),并经NaBH4还原,合成了5个N-苯氧苯基取代的α-氨基酸衍生物,以二苯醚类除草剂三氟羧草醚为对照药剂,测定化合物对水稻幼苗根、芽的室内生物活性;以空心莲子草为试验材料,以苯氧苯基甘氨酸乙酯(IIa)为试验药剂,喷雾处理空心莲子草后采用HPLC法测定该化合物在植株根中的含量来判断其传导性。【结果】化合物Ⅰa和Ⅱa对水稻幼苗的根、芽的生长均具有一定的抑制作用,化合物Ⅱb在低浓度下对水稻芽具有促进生长的作用,化合物Ⅱc和Ⅱd在低浓度下对水稻幼苗的根具有促进生长的作用;供试化合物在光照条件下的生物活性均比在黑暗条件下高;利用化合物Ⅱa 300 mg.L-1的药液喷雾处理空心莲子草地上部分12 h后,在其根部检测到目标化合物(IIa)含量为8.67 mg.kg-1 FW。【结论】二苯醚类化合物衍生出氨基酸基团后,所得衍生物既保留了二苯醚类除草剂的需光性除草活性特点,又增加了经由植物韧皮部向根部的传导性。
【Objective】 The objective of this study is to synthesize N-phenoxy-phenyl α-amino acid derivatives and determine their biological activities and translocation in plant seedlings.【Method】By condensation reaction of the amino diphenyl ether and ethyl glyoxylate or ethyl pyruvate respectively,two schiff base compounds(Ia-Ib) were synthesized,and reduced by NaBH4,five kinds of compounds of N-phenoxy-phenyl α-amino acid derivatives were synthesized.Taking the acifuorfen as the comparison,the in vivo toxicities of the 7 kinds of compounds to the rice seedling root and bud were determined.The translocation of the N-phenoxy-phenyl glycine ethyl ester(IIa) in seedlings of Alternanthera philoxeroides(Mart.) was determined by detecting the concentration of the compound IIa in roots of seedlings with HPLC after the seedlings were sprayed with the compound IIa.【Result】Compounds Ia and IIa had inhibitory effects on growth of roots and buds of the paddy rice seedlings.At low concentration,the compound IIb promoted the growth of the paddy rice seedling's buds and the compound IIc and IId promoted the growth of the paddy rice seedling's root.These compounds had higher bioactivities under illumination than under darkness.After the above-ground part of the Alternanthera philoxeroides was treated with 300 mg·L-1 compound IIa 12 h later,the compound IIa could be detected in the root part of Alternanthera philoxeroides with the content of 8.67 mg·kg-1 FW.【Conclusion】The N-phenoxy-phenyl α-amino acid derivatives could maintain the light-requiring herbicidal activities of diphenyl herbicides,as well as improve the phloem mobility in plant seedlings.