苯并嗪-1-羧酸-丙氨酸缀合物的合成、杀菌活性和韧皮部移动性。
Synthesis, fungicidal activity and phloem mobility of phenazine-1-carboxylic acid-alanine conjugates.
机构信息
Agricultural School, Yangtze University, Jingzhou, Hubei 434025, PR China.
Agricultural School, Yangtze University, Jingzhou, Hubei 434025, PR China.
出版信息
Pestic Biochem Physiol. 2017 Nov;143:8-13. doi: 10.1016/j.pestbp.2017.10.004. Epub 2017 Oct 16.
Phenazine-1-carboxylic acid (PCA) is a natural product that has been proven effective against a number of soil-borne fungal phytopathogens and registered for biofungicide against rice sheath blight in China. In order to improve the phloem mobility of phenazine-1-carboxylic acid (PCA), four PCA derivatives were designed and synthesized by conjugating PCA with l-alanine methyl ester, d-alanine methyl ester, l-alanine and d-alanine respectively. In vitro and planta bioassays results showed that conjugates L-PAM and D-PAM exhibited higher fungicidal activities against Rhizoctonia solani Kuhn than PCA while L-PA and D-PA were less active than PCA. The concentration of conjugates in Ricinus communis phloem sap was determined by HPLC. The results showed that only L-PA exhibited phloem mobility among these conjugates, and its concentration in Ricinus communis phloem sap increased with the increase of time (the maximum concentration was 12.69μM within 5h). However, the results of pot experiments showed that L-PA and other conjugates didn't exhibited the inhibition for the growth of Rhizoctonia solani Kuhn in the lower leaves after treatment in the upper leaves of rice seedlings. This may be due to the poor plant absorbility for them or their too little amount of accumulation in the lower leaves.
吩嗪-1-羧酸（PCA）是一种天然产物，已被证明对许多土传真菌植物病原体有效，并在中国注册为防治水稻纹枯病的生物杀菌剂。为了提高吩嗪-1-羧酸（PCA）的韧皮部移动性，将 PCA 分别与 l-丙氨酸甲酯、d-丙氨酸甲酯、l-丙氨酸和 d-丙氨酸偶联，设计并合成了 4 种 PCA 衍生物。体外和植物生物测定结果表明，与 PCA 相比，偶联物 L-PAM 和 D-PAM 对丝核菌具有更高的杀菌活性，而 L-PA 和 D-PA 的活性低于 PCA。通过 HPLC 测定了这些偶联物在蓖麻韧皮部汁液中的浓度。结果表明，只有 L-PA 具有韧皮部移动性，其在蓖麻韧皮部汁液中的浓度随时间的增加而增加（5h 内最大浓度为 12.69μM）。然而，盆栽试验结果表明，L-PA 和其他偶联物在处理水稻幼苗上部叶片后，对下部叶片中丝核菌的生长没有表现出抑制作用。这可能是由于它们在植物体内的吸收较差或在下部叶片中的积累量太少。
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