芳基吡唑氟尿嘧啶类化合物的设计、合成与杀虫活性研究  

Design, Synthesis, Insecticidal Activity and Structure-Activity Relationship of Aryl Pyrazole 5-Fluorouracil Derivatives

作　　者：傅晓东[1] 陈月[1] 杨阳[1] 贺书泽 沈陈[1] 万嵘[1] 

机构地区：[1]南京工业大学理学院,南京210009 [2]江苏扬农化工股份有限公司,扬州225009

出　　处：《有机化学》2014年第10期2090-2098,共9页Chinese Journal of Organic Chemistry

基　　金：江苏省科技厅科技支撑计划(农业)(No.BE2011352)资助项目~~

摘　　要：利用以γ-氨基丁酸(GABA)受体抑制剂芳基吡唑类杀虫剂的关键结构5-氨基-3-氰基-1-(取代苯基)吡唑为基本母核,设计、合成了26个创新结构芳基吡唑氟尿嘧啶化合物.目标化合物结构均采用1H NMR,FTIR和元素分析进行了结构确证,以小菜蛾和库蚊为靶标进行了杀虫活性测试.评价结果表明创制化合物具有优越的杀虫活性:在浓度为1000 mg·L-1时,化合物5a^5c,5e,5m及5u对库蚊具有100%的杀虫活性;在浓度为400 mg·L-1时,化合物5p对小菜蛾具有94.5%的杀虫活性.初步构效关系研究表明:苯环上取代基种类及位置等对化合物的生物活性有重要的影响.On the basis of the key structure of γ-amino butyric acid （GABA） receptor inhibitor aryl pyrazole pesticides, a series of novel aryl pyrazole derivatives containing 5-fluorouracil were designed and synthesized via the key intermediate 5-amino-3-cyano-1-（substituted phenyl）pyrazole. The structures of target compounds were confirmed by ^1 H NMR, FTIR and elemental analysis, and their insecticidal activities were evaluated against diamondback moth （Plutella xylostella） and mosquito （Culex pipiens）. The results of bioassays indicated that aryl pyrazole 5-fluorouracil derivatives exhibited satisfactory insecticidal activities. The insecticidal activities of compounds 5a^5c, 5e, 5m and 5u against mosquito were all 100% at 1000 mg·L^-1. Moreover, the compound 5p exhibited good lethal activity （94.45%） against P. xylostella at the concentration of 400 mg·L^-1. The results also indicated that the type and position of substituent on the phenyl ring play crucial roles on the biological activities of the compounds.

关 键 词：芳基吡唑 5-氟尿嘧啶 合成 杀虫活性 

分 类 号：O626[理学—有机化学] TQ450.1[理学—化学]