N-取代苯甲酰-N'-(5-甲氧基-2-甲硫基嘧啶-4-胺基)(硫)脲的设计、合成及生物活性研究
收稿日期: 2014-04-24
修回日期: 2014-05-20
网络出版日期: 2014-07-02
基金资助
山东省中青年科学家科研奖励基金(No.BS2011NY013)、山东农业大学青年创新基金(No.23682)、国家自然科学基金(No.21102173)、山东省科技发展计划(No.2013GZX20109)和华南农业大学校长科学基金(No.4200-K13014)资助项目.
Design, Synthesis and Biological Activities of N-(Substitutedbenzoyl)-N'-(5-methoxyl-2-methylsulfanylpyrimidin-4-amino)(thio) Ureas
Received date: 2014-04-24
Revised date: 2014-05-20
Online published: 2014-07-02
Supported by
Project supported by the Promotive Research Fund for Excellent Young and Middle-aged Scientists of Shandong Province (No.BS2011NY013), the Innovation Fund for the Youth of Shandong Agricultural University (No.23682), the National Natural Science Foundation of China (No.21102173), the Project of Development of Science and Technology of Shandong Province (No.2013GZX20109) and the President Science Foundation of South China Agricultural University (No.4200-K13014).
为了寻找新型高效、低毒、环境友好的农药先导化合物, 以取代苯甲酸、α-甲氧基乙酸甲酯和甲酸乙酯为起始原料, 设计合成了22个未见报道的N-取代苯甲酰-N'-(5-甲氧基-2-甲硫基嘧啶-4-胺基)(硫)脲10a~10v, 其结构经1H NMR, IR和元素分析表征和确认. 对目标化合物进行初步杀菌活性和昆虫生长调节活性筛选, 生测结果表明: 部分化合物具有较好的杀菌活性, 如化合物10m和10p在50 mg/mL下对黄瓜灰霉菌和油菜菌核菌的抑制率均超过70%, 其中对后者的抑制率高于对照药剂95%百菌清; 一些化合物对2~3龄库蚊幼虫表现出优良的昆虫生长调节活性, 化合物10o和10r对幼虫的未羽化率达97.8%, 化合物10t对幼虫具有100%灭杀活性.
李成坤 , 姜林 , 王悦 , 万福贤 , 张沛之 , 李映 , 崔紫宁 . N-取代苯甲酰-N'-(5-甲氧基-2-甲硫基嘧啶-4-胺基)(硫)脲的设计、合成及生物活性研究[J]. 有机化学, 2014 , 34(11) : 2296 -2303 . DOI: 10.6023/cjoc201404043
In order to find new lead compounds with high effciency, low toxicity and environmental-friendly contribution, a series of novel N-(substituted benzoyl)-N'-(5-methoxyl-2-methylsulfanylpyrimidin-4-amino)(thio) ureas were designed and synthesized from substituted benzoic acids, α-methoxyl methyl acetate and ethyl formate. Their structures were confirmed by 1H NMR, IR and elemental analysis. The preliminary bioassay results indicated that some compounds exhibited considerate fungicidal activity. Among them compounds 10m and 10p showed more than 70% inhibitory rate to Botrytis cinerea and Sclerotinia sclerotiorum at 50 mg/mL, and the inhibitory rate against Sclerotinia sclerotiorum was higher than the control fungicide 95% chlorothalonil. Some compounds showed obvious insect growth regulation activity against 2~3 instar Culex larvae, compounds 10o and 10r showed 97.8% revised uneclosion rate, and compound 10t exhibited 100% insecticidal activity.
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