含七氟异丙基的3-酰氨基苯甲酰胺类化合物的合成及杀虫活性
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摘要
设计合成了一系列新颖的含七氟异丙基的3-酰氨基苯甲酰胺类化合物,其结构均经核磁共振氢谱、质谱和高分辨质谱确证。初步生物活性测试结果表明,在20 mg/L下,部分化合物对小菜蛾Plutella xylostella具有较高的杀虫活性,其中8j在4 mg/L下对小菜蛾的致死率达100%。
A series of novel 3-acylaminobenzamides containing heptafluoroisopropyl group were synthesized,and their structures were characterized by 1H NMR,ESI-MS and HRMS.Their insecticidal activity indicated that some of the title compounds exhibited moderate to high insecticidal activity against diamondback moth(Plutella xylostella) at 20 mg/L,while compound(8j) showed mortality rate of 100% at the concentration of 4 mg/L.
A series of novel 3-acylaminobenzamides containing heptafluoroisopropyl group were synthesized,and their structures were characterized by 1H NMR,ESI-MS and HRMS.Their insecticidal activity indicated that some of the title compounds exhibited moderate to high insecticidal activity against diamondback moth(Plutella xylostella) at 20 mg/L,while compound(8j) showed mortality rate of 100% at the concentration of 4 mg/L.
引文
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[3]YOSHIDA K,WAKITA T,KATSUTA H,et al.Insecticide foragricultural or horticultural use and method of use thereof:WO2005021488A1[P].2005-10-03.
[4]MAIENFISCH P,ZAMBACK W,JUNG P,et al.Insecticidalcompounds:WO 2008000438A1[P].2008-01-03.
[5]YANAGI A,WATANABE Y,WADA K,et al.Insecticidal 3-acylaminobenzanilides:WO 2007017075A1[P].2007-02-15.
[6]ONISHI M,YOSHIURA A,KOHNO E,et al.Aniline derivativeand process for producing the same:EP 1006102A2[P].2000-06-07.
[7]MAIENFISCH P,GODFREY C R A,JUNG P J M,et al.Insecticidal compounds:WO 2010127928A1[P].2010-11-11.
[8]KOBAYASHI Y,DAIDO H,KATSUTA H,et al.Amidederivative,pest control agent containing the amide derivative anduse of the pest control agent:WO 2010018714A1[P].2010-02-18.
[9]JUNG P J M,GODFREY C R A,HUETER O F,et al.4-Cyano-3-benzoylamino-N-phenyl-benzamides for use in pest control:WO 2010127926A1[P].2010-11-11.
[10]MAIENFISCH P,GODFREY C R A,JUNG P J M.N-(4-Perfluoroalkyl-phenyl)-4-triazolyl-benzamides as nsecticides:WO2010127927A1[P].2010-11-11.
[11]JUNG P,GODFREY C R A,LUTZ W,et al.Insecticidalcompounds:WO 2008107091A1[P].2008-09-12.
[12]USUI S,FUKUCHI T,KINOSHITA S.3-Aminoxalyl-aminobenzamide derivatives and insecticidal and miticidal agentscontaining same active ingredient:US 20120022263A1[P].2012-01-26.
[13]HANSEN P E,KAMOUNAH F S,ULLAH S.Intramolecularhydrogen bonding of o-hydroxyesters and related compoundsevaluated by deuterium isotope effects on 13C chemical shifts andprincipal component analysis[J].J Mol Struct,2007,844-845:300-307.
[14]YAN Y,QIN B,SHU Y Y,et al.Helical organization in foldablearomatic oligoamides by a continuous hydrogen-bonding network[J].Org Lett,2009,11(6):1201-1204.
[15]胡伟群,朱卫刚,陈定花,等.甲氧基丙烯酸酯类新化合物ZJ1621的生物活性[J].农药学学报,2007,9(3):240-244.HU Weiqun,ZHU Weigang,CHEN Dinghua,et al.Biologicalactivity of novel strobilurin compound ZJ1621[J].Chin J PesticSci,2007,9(3):240-244.(in Chinese)
[16]TOHNISHI M,NAKAO H,FURUYA T,et al.Flubendiamide,anovel insecticide highly active against lepidopterous insect pests[J].J Pestic Sci,2005,30(4):354-360.
[17]YAN Y,QIN B,REN C L,et al.Synthesis,structuralinvestigations,hydrogen-deuterium exchange studies,andmolecular modeling of conformationally stablilized aromaticoligoamides[J].J Am Chem Soc,2010,132(16):5869-5879.