文献类型：期刊文献

中文题名：3-对[艹孟]烯-1-磺酰胺类化合物的合成及其除草活性

英文题名：Synthesis and Herbicidal Activity Investigation of p-Menth-3-en-1-sulfonamide Compounds

作者：张红梅[1,2,3] 陈玉湘[1,3] 徐士超[1,3] 王婧[1,2,3] 蒋建新[2] 赵振东[1,3]

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,生物质化学利用国家工程实验室,国家林业和草原局林产化学工程重点实验室,江苏省生物质能源与材料重点实验室,江苏南京210042;[2]北京林业大学材料科学与技术学院,北京100083;[3]南京林业大学江苏省林业资源高效加工利用协同创新中心,江苏南京210037

年份：2022

卷号：42

期号：1

起止页码：43-50

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:【CSCD2021_2022】；

基金：国家自然科学基金资助项目(31870557)。

语种：中文

中文关键词：松节油;3-对[艹孟]烯-1-胺;植物源除草剂;磺酰胺衍生物;除草活性

外文关键词：turpentine;p-menth-3-en-1-amine;botanical herbicides;sulfamide compounds;herbicidal activity

分类号：TQ35

摘要：以松节油为原料合成了3-对[艹孟]烯-1-胺,继而以磺酰氯为磺酰化试剂、三乙胺为缚酸剂,合成了10种3-对[艹孟]烯-1-磺酰胺类化合物(2a~2j)。通过FT-IR、^(1)H NMR、^(13)C NMR和LC-MS对所合成化合物的结构进行了表征,并评价了其对稗草的芽后除草活性。研究结果表明:3-对[艹孟]烯-1-磺酰胺类化合物的收率为60%~87%,各种结构表征图谱与化合物特征相符,表明成功合成了目标化合物。部分化合物对稗草的生长抑制作用明显,其中3-对[艹孟]烯-1-丙基磺酰胺(2f)的除草活性最好,对茎长和根长的半数抑制浓度(IC_(50))值分别为0.36和0.17 mmol/L。细胞毒性试验结果表明:3-对[艹孟]烯-1-基磺酰胺类化合物毒性较低,对正常人脐静脉血管内皮细胞HUVEC-C和小鼠胚胎成纤维细胞BALB/C 3T3的体外增殖均无显著抑制。构效关系分析表明:含烷基的磺酰胺衍生物的除草活性明显高于含芳基的,当烷基为3个碳原子时活性最好,但是当烷基上连有吸电子基团时会减弱其活性;苯环或萘环上连有给电子基团(甲基、甲氧基)时活性比连吸电子基团(F、Cl、Br)要好。
Ten p-menth-3-en-1-sulfamide compounds(2a-2j)were synthesized by using turpentine as start material,sulfonyl chloride as sulfonylation reagent,triethylamine as acid binding agent.Their structures were characterized by FT-IR,^(1)H NMR,^(13)C NMR and LC-MS.The post-emergence herbicidal activities of them against Echinochloa crusgalli were evaluated.The results showed that the yields of p-menth-3-en-1-sulfamide compounds were 60%-87%.The structural characterization spectra were consistent with the compounds,indicating that the target compounds had been successfully synthesized.Some compounds showed obvious inhibition activities to the growth of E.crusgalli.Among them,p-menth-3-en-1-propyl-sulfamide(2f)showed the best herbicidal activity against E.crusgalli.And the IC_(50) values of it against the stem and root growth of E.crusgalli were 0.36 and 0.17 mmol/L,respectively.Cytotoxicity assays results showed that p-menth-3-en-1-sulfamide compounds had no significant inhibition against cell proliferation of normal human HUVEC-C cells and mouse fibroblasts BALB/C 3T3 cells in vitro.Structure-activity relationship analysis showed that the herbicidal activity of alkyl sulfonamide derivatives was significantly higher than that of aryl groups and reached the best when the alkyl group containing three carbon atoms.However,the herbicidal activity was weakened when the alkyl group was connected with electron-absorbing groups.The herbicidal activities of benzene or naphthalene rings with electron-donating groups(methyl,methoxyl)were better than those of electron-absorbing groups(F,Cl,Br).