摘要
具有异喹啉-1(2H)-酮骨架的天然产物分布广泛且有丰富多样的生物活性,为进一步明确该类化合物的农用抑菌活性,本文利用Castagnoli-Cushman反应及酯化反应合成了22个具有该骨架的四氢异喹啉酮-4-羧酸(酯)类化合物。离体抑菌活性测定结果表明,在100μg/mL下,5a~5k和6a~6f对油菜菌核病菌菌丝生长抑制率高于80%,其中5k活性最高,EC_(50)值为5.8μg/mL,但低于对照药剂啶酰菌胺(EC_(50)=0.094μg/mL)。初步构效关系分析表明,在N上引入苯基要优于烷基,苯基上引入不同取代基后抑菌活性均有所提高且表现出位置和数目的选择性;C3位苯基和C4位羧基引入取代基对活性不利。室内离体叶片法结果表明,在500μg/mL下,5k的保护作用防治效果为94.6%,与啶酰菌胺在10μg/mL下的防治效果(95.8%)相当。本研究可为该类化合物的进一步结构优化提供借鉴。
Compounds bearing structurally unique isoquinolin-1(2H)-one scaffold were found to be widely distributed in various organisms and they exhibited a broad spectrum of biological activities.In the present study,22 derivatives of the isoquinolin-1(2H)-one scaffold were synthesized by CastagnoliCushman reaction and esterification reaction and their antifungal activity was evaluated against7 phytopathogens.The in vitro bioassay results indicated that the mycelial growth inhibition rates of compounds 5a-5k and 6a-6f were higher than 80%against Sclerotinia sclerotiorum at the concentration of 100μg/mL.Compound 5k was the most potent activity with the EC_(50)value of 5.8μg/mL,which was lower than the commercial boscalid(EC_(50)=0.094μg/mL).The structure-activity relationship analysis revealed that the phenyl on N atom site is superior to the alkyl,and the introduction of different substituents to the phenyl group could improve the antifungal activity,which was subject to the positional selectivity and the number of substituents on the phenyl group.However,introducing different substituents at C3 phenyl and C4 carboxyl group were unfavorable for the activity.The preventive control efficacy of 5k was 94.6%at 500μg/mL,which was comparable to that of boscalid at 10μg/mL(95.8%).Taken together,these results could provide some important cues for further optimization of tetrahydroisoquinolone-4-carboxylic acid derivatives.
作者
李敏
员春霞
房雅丽
张治家
王德龙
LI Min;YUN Chunxia;FANG Yali;ZHANG Zhijia;WANG Delong(College of Plant Protection,Shanxi Agricultural University,Taigu 030801,Shanxi Province,China)
出处
《农药学学报》
CAS
CSCD
北大核心
2023年第1期62-72,共11页
Chinese Journal of Pesticide Science
基金
国家自然科学基金青年基金(31901909)
山西省现代农业产业技术体系建设专项资金(2022-05)。
