取代酰腙类化合物的合成及其杀虫活性研究
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摘要
以对氯苯甲酸、甲醇、水合肼、对硝基苯甲醛、对甲氧基苯甲醛、苯乙酮为原料,合成了对硝基苯甲醛对氯苯甲酰腙、对甲氧基苯甲醛对氯苯甲酰腙及苯乙酮对氯苯甲酰腙。目标化合物的结构通过核磁共振氢谱、元素分析和红外光谱进行了表征,并试验了目标化合物对菜粉蝶幼虫的杀虫活性。活性筛选试验结果表明,对硝基苯甲醛对氯苯甲酰腙的触杀活性和胃毒活性最强。系列浓度试验表明,处理24 h后,对硝基苯甲醛对氯苯甲酰腙对菜粉蝶幼虫的触杀活性和胃毒活性的EC50分别为497.85 mg/L、287.01 mg/L;处理48 h后,二者分别为272.21 mg/L、145.75 mg/L。
Taking p-chlorobenzoic acid,methanol,hydrazine hydrate,p-nitrobenzaldehyde,p-methoxybenzaldehyde and acetophenone as materials,p-nitrobenzaldehyde p-chlorobenzoyl hydrazone,pmethoxybenzaldehyde p-chlorobenzoyl hydrazone and acetophenone p-chlorobenzoyl hydrazone were synthesized in lab.Their structures were confirmed by 1HNMR,elemental analysis and the infrared spectrum.The insecticidal activities of target compounds were tested against Pieris rapae larvae in lab.The results showed that p-nitrobenzaldehyde p-chlorobenzoyl hydrazone had the strongest contact toxicity and stomach toxicity.Insecticidal activities of series of concentrations of p-nitrobenzaldehyde p-chlorobenzoyl hydrazone were tested against P.rapae and the EC50 of contact toxicity and stomach toxicity24 h after treatment were 497.85 mg / L、287.01 mg / L and 48 h after treatment were 272.21 mg / L and145.75 mg / L,respectively.
Taking p-chlorobenzoic acid,methanol,hydrazine hydrate,p-nitrobenzaldehyde,p-methoxybenzaldehyde and acetophenone as materials,p-nitrobenzaldehyde p-chlorobenzoyl hydrazone,pmethoxybenzaldehyde p-chlorobenzoyl hydrazone and acetophenone p-chlorobenzoyl hydrazone were synthesized in lab.Their structures were confirmed by 1HNMR,elemental analysis and the infrared spectrum.The insecticidal activities of target compounds were tested against Pieris rapae larvae in lab.The results showed that p-nitrobenzaldehyde p-chlorobenzoyl hydrazone had the strongest contact toxicity and stomach toxicity.Insecticidal activities of series of concentrations of p-nitrobenzaldehyde p-chlorobenzoyl hydrazone were tested against P.rapae and the EC50 of contact toxicity and stomach toxicity24 h after treatment were 497.85 mg / L、287.01 mg / L and 48 h after treatment were 272.21 mg / L and145.75 mg / L,respectively.
引文
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[4]INAM A,SIDDIQUI S M,MACEDO T S,et al.Design,synthesis and biological evaluation of 3-[4-(7-chloro-quinolin-4-yl)-piperazin-1-yl]-propionic acid hydrazones as antiprotozoal agents[J].European Journal of Medicinal Chemistry,2014,75:67.
[5]MASSARICO SERAFIM R A,GONALVES J E,DE SOUZA F P,et al.Design,synthesis and biological evaluation of hybrid bioisoster derivatives of N-acylhydrazone and furoxan groups with potential and selective antiTrypanosoma cruzi activity[J].European Journal of Medicinal Chemistry,2014,82:418.
[6]张美丹,黄剑锋,张晔初,等.新型苯甲醛-β-咔啉-3-酰腙的合成及其除草活性[J].合成化学,2014,22(3):313.
[7]杨滋渊,宋斌,徐守卫,等.呋喃酰腙及其镍、锰配合物的合成与晶体结构及抑菌活性[J].无机化学学报,2014,30(3):585.
[8]康圣鸿,胡德禹,吴剑,等.含腙类结构化合物生物活性研究进展[J].农药,2012,51(4):238.
[9]张舟,李耀仓,范望喜,等.酰腙类化合物的研究进展[J].安徽农业科学,2010,38(13):6644.
[10]YAN Z N,WANG S Q,WANG H X,et al.Bismuth(III)PVC membrane ion selective electrodes based on two compounds:acylhydrazone and thiosemicarbazone with 1,3,4-thiadiazole[J].Materials Science and Engineering C-Materials for Biological Applications,2013,33(5):2562.
[11]徐焱,雷鹏,凌云,等.新型(3-取代苯基-2-丙烯-1-亚基)-苯甲酰腙类化合物的设计、合成及生物活性研究[J].有机化学,2014(6):1118.
[12]宋发辉,祝心德,王成刚,等.H2L及其金属配合物的合成和生物活性[J].武汉理工大学学报,2006,28(1):26.
[13]刘万云,霍平,梅光泉,等.橙皮素芳酰腙化合物的微波合成与抑菌活性研究[J].江西师范大学学报(自然科学版),2012,36(2):193.
[14]华世豪,邵维忠.乳油[M].北京:化学工业出版社,1985:80.
[15]慕立义.植物化学保护研究方法[M].北京:中国农业出版社,1994:47.
[16]吴文君.植物化学保护实验技术导论[M].西安:陕西科学技术出版社,1988:43.
[17]韩杰,周晓霞,陈思宝,等.含1,2,4-三唑酰腙类化合物的合成、结构表征及生物活性[J].有机化学,2014,34(4):741.
[18]岳敏,袁勤坤,金林红.含酰腙结构的新型吡唑酰胺衍生物对小菜蛾的生物活性[J].农药学学报,2012,14(4):449.