Synthesis and Fungicidal Activity of Diamide Compounds Based on the Metabolite of Benalaxyl

被引：3
|
作者：
Sun, Guoshao [1 ]
Wang, Lingna [1 ]
Jin, Shuhui [1 ]
Dong, Yanhong [1 ]
Lu, Huizhe [1 ]
Zhang, Jianjun [1 ]
机构：
[1] China Agr Univ, Beijing 100193, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 37卷 / 01期
基金：
美国国家科学基金会;
关键词：
benalaxyl; metabolite; diamide; synthesis; antifungal activity; ACID; DESIGN; WHEAT;
D O I：
10.6023/cjoc201608006
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Based on benalaxyl pesticide metabolite structure framework, fourteen novel diamide derivatives were synthesized by the reaction of amine and N-2-carboxyacetyl-N'-(2,6-dimethylphenyl)alanine methyl ester. Their structures were identified by H-1 NMR, C-13 NMR spectra and HRMS. The results of bioassay indicated that some compounds possess potential fungicidal activities against 8 kinds of bacteria, and the antibacterial activity of some compounds was better than that of benalaxyl. At a dosage of 5.0 X 10(-5) g/mL,, compound 7d displayed 94.2% antifungal activities against Rhizoctonia solani. Compound 8f displayed 87.1% and 88.9% antifungal activities against Phytophthora capsici and Rhizoctonia solani.
引用
收藏
页码：157 / 165
页数：9
相关论文
共 35 条
  • [1] Mereaptoamide-based non-hydroxamic acid type histone deacetylase inhibitors
    Anandan, SK
    Ward, JS
    Brokx, RD
    Bray, MR
    Patel, DV
    Xiao, XX
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (08) : 1969 - 1972
  • [2] Bruge D., 2005, [No title captured], Patent No. [WO2005005389A3, 2005005389, WO 2005005389]
  • [3] Synthesis and Biological Activities of Novel Analogues of Phthalamide Containing Acylurea and Acylthiourea
    Chen, Youwei
    Wan, Yingying
    Liu, Qiaoxia
    Liu, Jingbo
    Xiong, Lixia
    Yu, Shujing
    Li, Zhengming
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (04) : 882 - 889
  • [4] CHEN Z, 2015, SHOCK VIB, V2015, P1, DOI DOI 10.1155/2015/390134
  • [5] Dong X. X., 1989, MED PHILOS, V2, P55
  • [6] Catalytic reductive N-alkylation of anilines. Application to the synthesis of N-aryl aminoacid precursors.
    Fache, F
    Valot, F
    Milenkovic, A
    Lemaire, M
    [J]. TETRAHEDRON, 1996, 52 (29) : 9777 - 9784
  • [7] Fildes P, 1940, LANCET, V1, P955
  • [8] Design of non-nucleoside inhibitors of HIV-1 reverse transcriptase with improved drug resistance properties. 2.
    Freeman, GA
    Andrews, CW
    Hopkins, AL
    Lowell, GS
    Schaller, LT
    Cowan, JR
    Gonzales, SS
    Koszalka, GW
    Hazen, RJ
    Boone, LR
    Ferris, RG
    Creech, KL
    Roberts, GB
    Short, SA
    Weaver, K
    Reynolds, DJ
    Milton, J
    Ren, JS
    Stuart, DI
    Stammers, DK
    Chan, JH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (24) : 5923 - 5936
  • [9] Enantiomerization and Enantioselective Bioaccumulation of Benalaxyl in Tenebrio molitor Larvae from Wheat Bran
    Gao, Yongxin
    Chen, Jinhui
    Wang, Huili
    Liu, Chen
    Lv, Xiaotian
    Li, Jianzhong
    Guo, Baoyuan
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2013, 61 (38) : 9045 - 9051
  • [10] PARA-NITROPHENYL 3-DIAZOPYRUVATE AND DIAZOPYRUVAMIDES, A NEW FAMILY OF PHOTOACTIVATABLE CROSS-LINKING BIOPROBES
    GOODFELLOW, VS
    SETTINERI, M
    LAWTON, RG
    [J]. BIOCHEMISTRY, 1989, 28 (15) : 6346 - 6360
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