农药学学报2024，Vol.26Issue(2)：324-336,13.DOI:10.16801/j.issn.1008-7303.2024.0012
N-(5-(3,5-二硝基苯基)噻唑-2-基)-2-苯氧乙酰胺类化合物的设计、合成及除草活性
Design,synthesis and herbicidal activity of novel N-(5-(3,5-dinitrophenyl)thiazol-2-yl)-2-phenoxyacetamide compounds
摘要
Abstract
In order to discover highly active herbicidal compounds,29 derivatives of N-(5-(3,5-dinitrophenyl)thiazol-2-yl)-2-phenoxyacetamide(Ⅵaa-Ⅵbc)were synthesized and characterized by 1H NMR,13C NMR,and HRMS.The spatial configuration of compoundⅥaa was determined using X-ray single crystal diffraction.Barnyard grass and lettuce were used as target organisms for herbicidal activity testing using a Petri dish method.The results showed that most of the target compounds exhibited inhibition rates of over 70%against barnyard grass and lettuce at a concentration of 100 mg/L.Stem and leaf spray experiments demonstrated that compoundsⅥam,Ⅵas,Ⅵat,Ⅵav,andⅥaw inhibited the fresh weight of dicotyledonous plant lettuce by over 80%at a concentration of 375 g/hm2,with compoundⅥas showing 100%inhibition.Crop safety experiments have demonstrated that compoundⅥas at a dosage of 750 g/hm2 causes varying degrees of phytotoxicity to maize,sorghum,rice,soybeans,flax,and rapeseed.However,the phytotoxicity to sorghum is the lowest among these crops and notably lower than the control herbicide 2,4-D.The results of the transmission electron microscope analysis showed that treatment of lettuce leaves with a concentration of 18.17 g/hm2 for 72 hours,the chloroplast membrane of the leaves twisted and deformed,the thylakoid layers of the chloroplasts were disorganized,and partial vesicles underwent rupture.Enzyme activity measurement results showed that compoundⅥas exhibited a stimulatory effect followed by suppression on catalase(CAT)and hydrogen peroxide(H2O2).It can be inferred that compound VIas inhibits the normal growth of lettuce by damaging the chloroplast structure and affecting the activity of CAT and H2O2,showing an initial promotion followed by inhibition effect.关键词
噻唑/苯氧乙酰胺/除草活性/作物安全性Key words
thiazole/phenoxyacetamide/herbicidal activity/crop safety分类
化学化工引用本文复制引用
刘娜,万远会,韩进财,李皓,柏振东,柏浩东,罗丁峰,李祖任..N-(5-(3,5-二硝基苯基)噻唑-2-基)-2-苯氧乙酰胺类化合物的设计、合成及除草活性[J].农药学学报,2024,26(2):324-336,13.基金项目
湖南省农业科技创新资金项目(2023CX115) （2023CX115）
湖南省自然科学基金面上项目(2023JJ30342).Supported by Scientific-Innovative of Hunan Agricultural Sciences and Technology(No.2023CX115)and Natural Science Foundation of Hunan Province(No.2023JJ30342). （2023JJ30342）
