摘要/Abstract

以α-甲氧基乙酸甲酯、甲酸乙酯和取代苯甲酸为起始原料，经过环化、Dimroth重排和亲核加成等反应，合成了一系列结构新颖的N-取代苯甲酰基-N'-4，7-二甲氧基-[1，2，4]三唑并[1，5-c]嘧啶（硫）脲类化合物11a～11q.目标化合物的结构通过IR、¹H NMR、¹³C NMR和元素分析进行了确认.初步生物活性测试结果表明，在50 mg·L^-1下，大部分化合物具有一定的杀菌活性，其中N-（2-氯苯甲酰基）-N'-4，7-二甲氧基-[1，2，4]三唑并[1，5-c]嘧啶硫脲（11m）对黄瓜灰霉菌的抑制率为67.25%.化合物均对2～3龄库蚊幼虫表现一定的昆虫生长调节活性，7个化合物的校正未羽化率高于70%，其中N-（4-甲基苯甲酰基）-N'-4，7-二甲氧基-[1，2，4]三唑并[1，5-c]嘧啶硫脲（11l）的校正未化蛹率和校正未羽化率均达100%，与对照药剂5%（质量分数）吡丙醚乳液相当.构效关系研究表明，苯环上吸电子基团的引入有利于杀菌活性的提高，而给电子基团的引入则有利于昆虫生长调节活性的提高.苯甲酰基脲类化合物11a～11i的杀菌活性普遍优于苯甲酰基硫脲类化合物11j～11q，而苯甲酰基硫脲类化合物则表现出更好的昆虫生长调节活性.
关键词: 几丁质, 苯甲酰基(硫)脲, 三唑并嘧啶, 杀菌活性, 昆虫生长调节活性
A series of novel N-(substitutedbenzoyl)-N'-4,7-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidine (thio)ureas (11a~11q) were synthesized from α-methoxyl methyl acetate, ethyl formate and substituted benzoic acids by cyclization, Dimroth rearrangement and nucleophilic addition reactions. The structures of products were confirmed by IR, ¹H NMR, ¹³C NMR and elemental analysis. The preliminary bioassay showed that most of the compounds displayed positive fungicidal activity at 50 mg·L^-1. Among them, N-(2-chlorobenzoyl)-N'-4,7-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidinethiourea (11m) exhibited an inhibition rate of 67.25% against B. cinerea. All compounds showed certain insect growth regulation activities against 2~3 instar culex larvae, in which seven compounds exhibited revised uneclosion rate higher than 70%. N-(4-methylbenzoyl)-N'-4,7-dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidinethiourea (11l) showed excellent insecticidal activity, which was equivalent to the control 5% (mass fraction) pyriproxyfen. The preliminary structure-activity relationship analysis showed that compounds with electron-withdrawing group on the phenyl ring showed higher fungicidal activities, while compounds with electron-donating group exhibited higher insect growth regulation activities. Benzoylureas displayed higher fungicidal activities and benzoylthioureas exhibited good insect growth regulation activities.
Key words: chitin, benzoyl (thio) urea, triazolopyrimidine, fungicidal activity, insect growth regulation activity


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