文献类型：期刊文献

中文题名：四氢芳樟基酰胺类化合物的合成及除草活性研究

英文题名：Synthesis and Herbicidal Activity of Tetrahydrolinalyl Amides

作者：张红梅[1,2] 王婧[1,2] 陈玉湘[1] 徐士超[1] 蒋建新[2] 赵振东[1]

第一作者：张红梅

机构：[1]中国林业科学研究院林产化学工业研究所,江苏省生物质能源与材料重点实验室,国家林业和草原局林产化学工程重点实验室,林木生物质低碳高效利用国家工程研究中心,江苏省林业资源高效加工利用协同创新中心,江苏南京210042;[2]北京林业大学材料科学与技术学院,北京100083

年份：2023

卷号：43

期号：3

起止页码：89-100

中文期刊名：林产化学与工业

外文期刊名：Chemistry and Industry of Forest Products

收录：CSTPCD;;Scopus;北大核心:【北大核心2020】；CSCD:【CSCD2023_2024】；

基金：国家自然科学基金资助项目(31870557)。

语种：中文

中文关键词：四氢芳樟醇;四氢芳樟胺;酰胺类化合物;除草活性

外文关键词：tetrahydrolinalool;tetrahydrolinalyl amine;amides;herbicidal activity

分类号：TQ35

摘要：以四氢芳樟醇为原料,设计合成了17种四氢芳樟基酰胺类化合物(2,4a~4p),得率64.8%~96.9%。通过FT-IR、^(1)H NMR、^(13)C NMR和HRMS表征了系列化合物的结构,并评价了目标化合物对黑麦草和稗草的除草活性。研究结果表明:四氢芳樟基酰胺类化合物对黑麦草和稗草均有一定的生长抑制活性,化合物2、4a、4o对黑麦草的萌芽前(芽前)除草活性最好,对黑麦草根长的半数抑制浓度(IC_(50))值分别为0.05、0.05和0.03 mmol/L(稍差于阳性对照草甘膦),对黑麦草茎长的IC_(50)值分别为0.06、0.05和0.05 mmol/L(优于草甘膦)。化合物4b对稗草根长和茎长的IC_(50)值分别为0.06和0.15 mmol/L(与草甘膦相同)。构效关系分析表明:四氢芳樟基酰胺类化合物在不同杂草间具有选择性;含烷基取代的化合物除草活性强于含苯环和呋喃环的,苯环上含给电子基团时活性强于含吸电子基团的,且给电子基团位于苯环邻位和间位时除草活性更好。
Seventeen tetrahydrolinalyl amides(2,4a-4p)were designed and synthesized using tetrahydrolinalool as starting material.Their structures were characterized by FT-IR,^(1)H NMR,^(13)C NMR and HRMS,then the herbicidal activities against Lolium perenne and Echinochloa crusgalli were evaluated.The results showed that the tetrahydrolinalyl amides exhibited certain growth inhibitory effects on L.perenne and E.crusgalli.Compounds 2,4a,4o showed the best pre-emergence herbicidal activity against L.perenne,where the inhibitory concentration_(50)%(IC_(50))values for the root growth of L.perenne were 0.05,0.05,and 0.04 mmol/L,respectively(weaker than that of the positive control glyphosate),and the IC_(50) values for the shoot of L.perenne were 0.06,0.05,and 0.05 mmol/L,respectively(stronger than that of glyphosate).The IC_(50) values of compound 4b on root and shoot growth of E.crusgalli were 0.06 and 0.15 mmol/L(equal to that of glyphosate),respectively.The structure-activity relationship analysis showed that tetrahydrolinayl amides exhibited selectivity among different weed species.The compounds containing alkyl group showed higher herbicidal activity than that of benzene ring and furan ring.The herbicidal activity of compounds with electron-donating group on benzene ring was stronger than that with electron-withdrawing group,exhibiting better activity when it was located at the ortho-and meta-position of benzene ring.