含吡唑杂环二酰胺类化合物的合成与杀虫活性研究

有机化学 ›› 2011, Vol. 31 ›› Issue (9): 1510-1515. 上一篇下一篇

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含吡唑杂环二酰胺类化合物的合成与杀虫活性研究

葛前建¹，陈列忠²，杜晓华*^,1

(¹浙江工业大学催化加氢研究中心杭州 310014)
(²浙江省农科院杭州 310021)

收稿日期:2010-12-29 修回日期:2011-03-23 发布日期:2011-04-28
通讯作者: 杜晓华 E-mail:duxiaohua@zjut.edu.cn

Synthesis and Insecticidal Activities of Pyrazole-heterocyclic Dia-mides

Ge Qianjian¹ Chen Liezhong² Du Xiao-hua*^,1

(¹Catalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014)
(²Zhejiang Academy of Agricultural Sciences, Hangzhou 310021)

Received:2010-12-29 Revised:2011-03-23 Published:2011-04-28

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摘要/Abstract

通过活性亚结构拼接, 合成16个含吡唑杂环的新型二酰胺类化合物, 其结构通过了IR, ¹H NMR和HRMS的表征, 其中目标化合物3h的结构经X单晶衍射进一步确认. 初步生测结果表明在500 mg/L浓度下, 部分化合物对粘虫和苜蓿蚜有致死活性|在100 mg/L浓度下部分化合物对茶尺蠖幼虫具有致死活性, 其中毒症状表现为拒食.

关键词: 活性亚结构, 双酰胺化合物, 鱼尼汀受体激活剂, 合成, 杀虫活性

16 novel pyrazole-heterocyclic diamides were synthesized according to the principle of combination of bioactive substructures, and their structures were characterized by IR, ¹H NMR and HRMS techniques. The crystal structure of 3h was determined by X-ray diffraction analysis. Preliminary bioassays showed that some compounds had lethal activities against Mythimna sepatara and Aphis medicaginis at the dosage of 500 mg/L|some of the compounds had lethal activities against the larvae of Ectropis oblique hypulina Wehrli at the dosage of 100 mg/L, the treated insects appeared to have anti-feeding effect.

Key words: bioactive substructure, diamides, ryanodine receptor activator, synthesis, insecticidal activity

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葛前建, 陈列忠, 杜晓华. 含吡唑杂环二酰胺类化合物的合成与杀虫活性研究[J]. 有机化学, 2011, 31(9): 1510-1515.

GE Qian-Jian, CHEN Lie-Zhong, DU Xiao-Hua. Synthesis and Insecticidal Activities of Pyrazole-heterocyclic Dia-mides[J]. Chin. J. Org. Chem., 2011, 31(9): 1510-1515.

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参考文献

[1]Qi,F.;Liu, Z.-L.; Xiong, L.-X.Synthesis and Insecticidal Activities of Novel Anthranilic Diamides Containing Modified N-Pyridylpyrazoles[J].J.Agric. Food Chem,2010,58:12327-12336

[2]Feng,M.-L.; Feng,Y.; Zhu,L.-X. J..Synthesis, Insecticidal Activity, and Structure-Activity Relationship of Trifluoromethyl-Containing Phthalic Acid Diamide Structures[J].Agric Food Chem,2010,58:10999-11006

[3]Liu,M.; Wang,Y.; Wangyang, W.-Z. .Design, Synthesis, and Insecticidal Activities of Phthalamides Containing a Hydrazone Substructure[J].J. Agric. Food Chem,2010,58:6858-6863

[4]Tohnishi, Masanori; Nakao, Hayami;. Preparation of phthalamides as agrohorticultural insecticides[J].EP 1006107,2000,:-

[5]Lahm, George Philip; Selby, Thomas Paul.Arthropodicidal anthranilamides[J].WO2003015519,2003,:-

[6]Hughes, Kenneth Andrew; Lahm, George Philip;.Preparation of cyano anthranilamide insecticides[J].WO2004067528,2004,:-

[7]John E. Casida.Pest Toxicology: The Primary Mechanisms of Pesticide Action[J].Chem. Res. Toxicol,2009,22:609-619

[8]Zhang,Y.-B. .鱼尼汀受体抑制剂类杀虫剂的研发新动向[J].,2009,31(2):3-6

[9]张一宾.鱼尼汀受体抑制剂类杀虫剂的研发新动向[J].世界农药,2009,31(2):3-6

[10]Kato,K.; Kiyonaka,S.; Sawaguchi,Y.; Tohnishi,M. .Molecular Characterization of Flubendiamide Sensitivity in the Lepidopterous Ryanodine Receptor Ca2+ Release Channel[J].Biochemictry,2009,48:10342-10352

[11]Daniel Cordova, Eric A. Benner, Matthew D. Sacher.The Novel Mode of Action of Anthranilic Diamide Insecticides: Ryanodine Receptor Activation[J].Synthesis and Chemistry of Agrochemicals Ⅶ,,17:223-234

[12]宋宝安金林红.-A.;Jin,L.-H. New Heterocylic Pesticide: Insecticide, Beijing,2010,p.71[J].新杂环农药（杀虫剂）,2009,:71-

[13]Hosie A M; Baylis H A; Buckingham S D;Sattela D B,.Actions of the insecticide fipronil, on dieldrin-sensitive and- resistant GABA receptors of Drosophila melanogaster[J].British Journal of Pharmacology,1995,115(6):909-912

[14] Hainzl D; Casida J E.Fipronil insecticide: novel photochemical desulfinylation with retention of neurotoxicity[J].Proceedings of the National Academy of Sciences of the United States of America,1996,93(23):12764-12767

[15]Nicalaou, K.C.; Baran, P.S.; Zhong, Y.L..New Synthetic Technology for the Synthesis of Hindered r-Diazoketones via Acyl Mesylates[J].Organic Letters,1999,1(6):883-886

含吡唑杂环二酰胺类化合物的合成与杀虫活性研究

Synthesis and Insecticidal Activities of Pyrazole-heterocyclic Dia-mides

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