N-(2-三氟甲基-4-氯苯基)-2-吡唑酰氨基环己烷基磺酰胺类化合物的合成与杀菌活性  

Synthesis and fungicidal activity of N-(2-trifluoromethyl-4-chlorophenyl)-2-pyrazoleamide cyclohexylsulfonamides

作　　者：孟司奇 杨永贵 纪明山[1] 祁之秋[1] 李兴海[1] MENG Siqi;YANG Yonggui;JI Mingshan;QI Zhiqiu;LI Xinghai(Plant Protection College,Shenyang Agricultural University,Shenyang 110866,China)

机构地区：[1]沈阳农业大学植物保护学院

出　　处：《农药学学报》2018年第5期568-576,共9页Chinese Journal of Pesticide Science

基　　金：辽宁省教育厅科学研究项目(LJNYB201611);辽宁省自然科学基金(2015020766);沈阳市中青年科技创新人才支持计划项目(RC170518)

摘　　要：吡唑酰胺类杀菌剂是近年新农药开发的热点。本研究采用EDCI/HOBt酰胺化法合成了14个结构新颖的N-（2-三氟甲基-4-氯苯基）-2-吡唑酰氨基环己烷基磺酰胺类化合物（3a^3n）,其结构均经1H NMR、13C NMR、质谱和元素分析确认,并用X-射线衍射法确定了化合物3g的单晶结构和立体构型。菌丝生长速率法试验结果表明,化合物3a、3e和3j对番茄灰霉病菌Botrytis cinerea KZ-9的EC50值分别为4.28、10.08和11.31 mg/L,抑菌活性不及对照药剂啶酰菌胺和腐霉利;但在孢子萌发试验中,目标化合物表现出与对照药剂相近的抑菌活性,在10 mg/L下有7个化合物对灰霉病菌孢子萌发的抑制率超过了85%;在番茄活体盆栽试验中,化合物3e在200 mg/L下对番茄叶片及其花上灰霉病菌的防治效果分别为77.5%和65.2%,高于对照药剂啶酰菌胺（防效分别为59.8%和30.3%）,有进一步研究的价值。Pyrazolecarboxamide derivatives have attracted much attention in the field of agrochemical discovery.With the objective of exploring the novel fungicides,14 novel N-（2-trifluoromethyl-4-chlorophenyl）-2-pyrazoleamide cyclohexylsulfonamides were obtained by amidation method using EDCI/HOBt.Their structures were characterized by ~1H NMR,^（13）C NMR,MS and elemental analysis.The crystal structure and stereo configuration of compound 3g were determined by X-ray diffraction.The bioactivities against Botrytis cinerea revealed that the synthesized compounds possessed good fungicidal activities.The bioactivities determined by the mycelium growth rate method showed that the EC50 values of compounds 3a,3e and 3j were 4.28,10.08 and 11.31 mg/L,respectively,and the activities were lower compared with the positive controls,namely boscalid and procymidone.However,7 compounds with the inhibition rates against spore germination of more than 85%showed better activities compared to the positive controls.The further in vivo bioassay showed that compound 3e exhibited better control effect（the control effect is 77.5%with tomato leaves and 65.2%with the flowers st the application concentration of 200 mg/L）than the commercial fungicides,which could be used as lead compounds for further study.

关 键 词：吡唑酰胺 有机合成 灰霉病菌 杀菌活性 构效关系 

分 类 号：O626.21[理学—有机化学] S482.2[理学—化学]