title: Synthesis and bioactivities of amino acid ester conjugates of phenazine-1-carboxylic acid.
abstract: Phenazine-1-carboxylic acid (PCA) is a natural product that has been characterized by special chemical structures, interesting bioactivities and has been registered for fungicide against rice sheath blight in China. Phloem mobility is of great significance to long-distance transport of systemic pesticides in plants. In order to improve the phloem mobility and bioactivities of PCA, seventeen PCA-amino acid ester conjugates were designed and synthesized by conjugating PCA with different amino-acid esters. The conjugates were evaluated for their fungicidal activities against Rhizoctonia solani Kuhn and their phloem mobility was determined by HPLC. Results showed that conjugates a, b, c, d, e, l, m and p (EC50values between 5.35 and 18.85μg/mL) were more active than PCA (25.66μg/mL). In particular, conjugates l and m exhibited the best fungicidal activities against Rhizoctonia solani Kuhn (EC50values of them were 6.47μg/mL and 5.35μg/mL respectively). All these conjugates didn't have phloem mobility.
authors: School of Agriculture, Yangtze University, Jingmi Road 88, Jingzhou 434025, China.
authors: Junfan
authors: J
authors: Niu
authors: School of Agriculture, Yangtze University, Jingmi Road 88, Jingzhou 434025, China.
authors: Jun
authors: J
authors: Chen
authors: School of Agriculture, Yangtze University, Jingmi Road 88, Jingzhou 434025, China.
authors: Zhihong
authors: Z
authors: Xu
authors: School of Agriculture, Yangtze University, Jingmi Road 88, Jingzhou 434025, China.
authors: Xiang
authors: X
authors: Zhu
authors: School of Agriculture, Yangtze University, Jingmi Road 88, Jingzhou 434025, China. Electronic address: wql106@163.com.
authors: Qinglai
authors: Q
authors: Wu
authors: School of Agriculture, Yangtze University, Jingmi Road 88, Jingzhou 434025, China. Electronic address: junkaili@sina.com.
authors: Junkai
authors: J
authors: Li
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D004951:Esterification; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D012275:Oryza / Q000382:microbiology; D010619:Phenazines / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D052585:Phloem / Q000187:drug effects / Q000378:metabolism / Q000382:microbiology; D010935:Plant Diseases / Q000382:microbiology; D012232:Rhizoctonia / Q000187:drug effects* / Q000502:physiology
chemical_list: D000596:Amino Acids; D005659:Fungicides, Industrial; D010619:Phenazines; C037165:1-phenazinecarboxylic acid
keywords: Amino acid esters; Fungicidal activity; Phenazine-1-carboxylic acid; Phloem mobility