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

作　　者：刘娜 万远会 韩进财 李皓 柏振东 柏浩东 罗丁峰 李祖任 LIU Na;WAN Yuanhui;HAN Jincai;LI Hao;BAI Zhendong;BAI Haodong;LUO Dingfeng;LI Zuren(Longping Branch,College of Biology,Hunan University,Changsha 410000,China;Hunan Provincial Key Laboratory for Biology and Control of Weeds,Hunan Academy of Agricultural Sciences,Changsha 410125,China)

机构地区：[1]湖南大学生物学院隆平分院,长沙410000 [2]杂草生物学及安全防控湖南省重点实验室,湖南省农业生物技术研究所,长沙410125

出　　处：《农药学学报》2024年第2期324-336,共13页Chinese Journal of Pesticide Science

基　　金：湖南省农业科技创新资金项目(2023CX115);湖南省自然科学基金面上项目(2023JJ30342).

摘　　要：为了发现高活性的除草化合物,设计合成了29个N-(5-(3,5-二硝基苯基)噻唑-2-基)-2-苯氧乙酰胺类衍生物(Ⅵaa~Ⅵbc),并通过核磁共振氢谱、碳谱和高分辨质谱确认其结构。利用X-射线单晶衍射确定化合物Ⅵaa的空间构型。以单子叶植物稗草和双子叶植物生菜为供试靶标,采用平皿法测试了目标化合物的除草活性。结果显示:多数化合物在100 mg/L下对稗草和生菜的生长抑制率达70%以上;整株茎叶喷雾法测定结果表明:在375 g/hm^(2)下,化合物Ⅵam、Ⅵas、Ⅵat、Ⅵav和Ⅵaw对生菜的鲜重抑制率达80%以上,其中化合物Ⅵas的抑制率为100%。作物安全性试验结果表明,在750 g/hm^(2)下,化合物Ⅵas对玉米、高粱、水稻、大豆、亚麻和油菜均有不同程度的药害,但对高粱的药害程度最小,明显低于对照药剂2,4-D。透射电子显微镜观察结果显示,用18.17 g/hm^(2)的化合物处理生菜叶片72 h后,叶片叶绿体被膜扭曲变形,叶绿体基粒片层排列散乱,部分类囊体发生断裂。酶活性测定试验结果表明,化合物Ⅵas对过氧化氢酶(CAT)活性和过氧化氢(H_(2)O_(2))含量均表现出先促进后抑制的效应。由此推断,化合物Ⅵas可能是通过破坏生菜叶绿体结构和影响CAT活性和H_(2)O_(2)含量而抑制生菜的正常生长。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 ^(1)H NMR,^(13)C NMR,and HRMS.The spatial configuration of compoundⅥaa was determined using Xray 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/hm^(2),with compoundⅥas showing 100%inhibition.Crop safety experiments have demonstrated that compoundⅥas at a dosage of 750 g/hm^(2) 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/hm^(2) 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(H_(2)O_(2)).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 H_(2)O_(2),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 

分 类 号：O626.25[理学—有机化学] TQ457.2[理学—化学]