松油烯基邻苯二甲酰亚胺衍生物的合成及其除草活性研究  

Synthesis and Herbicidal Activity of Terpinyl Phthalimide Derivatives

作　　者：张运 朱广通 卓梅芳 黄燕敏 莫启进 ZHANG Yun;ZHU Guangtong;ZHUO Meifang;HUANG Yanmin;MO Qijin(Guangxi Key Laboratory of Natural Polymer Chemistry and Physics,Nanning Normal University,Nanning 530001,China)

机构地区：[1]南宁师范大学广西天然高分子化学与物理重点实验室,广西南宁530001

出　　处：《林产化学与工业》2024年第2期103-110,共8页Chemistry and Industry of Forest Products

基　　金：广西自然科学基金资助项目(2021GXNSFAA220104)。

摘　　要：以α-松油烯(1)为起始原料,通过与丁炔二酸二甲酯发生Alder-Rickert反应制备了松油烯基丁烯二酸二甲酯(2),并通过闭环反应合成了松油烯基邻苯二甲酸酐(3),继而与一系列芳胺化合物发生取代反应,合成了13个新型结构的松油烯基邻苯二甲酰亚胺衍生物(4a~4m)。通过红外光谱、质谱、核磁共振氢谱和碳谱等手段对目标化合物的结构进行了表征,相关表征数据表明目标化合物4a~4m成功合成。初步的除草活性测试结果表明:在1.5 kg/hm^(2)施药量下,当采用茎叶处理时,大部分化合物对稗草、马唐、苘麻和反枝苋均具有一定的除草活性,其中化合物4b(R=p-CH_(3))和4c(R=p-OCH_(3))对苘麻的抑制活性最好,抑制率分别为62.2%和64.0%,均达到B级。Usingα-terpinene(1)as the starting material,dimethyl terpinylbutenedioate(2)was synthesized through its Alder-Rickert reaction with dimethyl butenedioate.Terpinyl phthalic anhydride(3)was subsequently synthesized by their ring-closing reaction.Afterwards,13 novel terpinyl phthalimide derivatives(4a-4m)were synthesized by the substitution reactions of compound 3 with a series of aromatic amine compounds.The structures of the target compounds were characterized by IR,ESI-MS,1 H NMR and 13 C NMR,and the successful synthesis of the target compounds 4a-4m was confirmed.Preliminary herbicidal activity tests results showed that most synthetic compounds exhibited certain herbicidal activity against Echinochloa crusgalli(L.)Beauv,Digitaria sanguinalis(L.)Scop.,Abutilon theophrasti Medicus and Amaranthus retroflexus when they were applied to the stems and leaves at a dosage of 1.5 kg/hm^(2).Among them,compounds 4b(R=p-CH_(3))and 4c(R=p-OCH_(3))showed the highest inhibitory activity and reached grade B against A.theophrasti Medicus with the inhibition rates of 62.2%and 64.0%,respectively.

关 键 词：松油烯 邻苯二甲酰亚胺 除草活性 合成 

分 类 号：TQ35[化学工程]