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Synthesis and insecticidal activities of new pyrethroid acid oxime ester derivatives

Progress in Natural Science:Materials International 2002年第4期 33-39页

作者： MA Jun’an, HUANG Runqiu and CHAI Youxin(Institute and State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China) Institute and State Key Laboratory of Elemento-organic Chemistry Nankai University Tianjin 300071 China

A series of compounds containing oxime-ester linkage in place of the ester linkage in pyrethroid ester are designed and prepared. Bioassay data of insecticidal activities of these compounds on Ostrinia nubilalis (H. ) and Culex pipines (L. ) are presented. Among them 4-dimethyaminobenzaldehyde oxime ester of 2, 2, 3, 3-tetramethylcyclopropanecarboxylic acid and 4-dimethyamino benzalde-hyde oxime ester of cyclopropanecarboxylic acid are found to be potent insecticide against Ostrinia nubilalis (H. ) . Structure-activity relationship of the compounds is discussed.

关键词： pyrethroids insecticides oxime-ester synthesis structure-activity relationship.

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Synthesis and Biological Activity of New Pyrethroid Acid oxime-esters Containing Pyrazole Ring

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Chemical Research in Chinese Universities 2003年第3期19卷 297-301页

作者： MA Jun-an HUANG Run-qiu FENG Lei SONG Jian QIU De-wen Institute and State Key Laboratory of Elemento-organic Chemistry Nankai UniversityTianjin 300071P.R.China

A series of compounds containing oxime-ester linkage and pyrazole ring(in place of the ester linkage and the alcohol moiety in pyrethroid ester) was designed and synthesized. The structures of all the compounds prepared were confirmed by 1H NMR and MS spectroscopy as well as elemental analyses. The bioassay data of those compounds against tobacco mosaic virus(TMV), cucumber mosaic virus(CMV), potato virus X(PVX) and potato virus Y(PVY) were presented. Among them compound 6i was found to possess significant plant antiviral activities. But all the compounds showed low insecticidal and acaricidal activities.

关键词： Pyrethroid oxime-ester Synthesis Pyrazole Plant antiviral activity

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Studies on the esterifications of 9-(hydroxyimino)-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one with acid chlorides under different conditions

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Chinese Chemical Letters 2008年第7期19卷 791-794页

作者： Ru Shu Sun Yang Wang Peng Xia Department of Medicinal Chemistry School of Pharmacy Fudan University Shanghai 200032 China

The esterifications of 9-（hydroxyimino）-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one （4） with acid chlorides afforded normal oxime-esters 3a-e in 35-78% yields in presence of excessive 4-dimethylaminopyridine as the acid scavenger, whereas the reactions gave unexpected 8-substituted products N-（8-chloro-4-methyl-2-oxo-2H-furo-[2,3-h]chromen-9-yl）amides （5a-c） and 4-methyl-2,9-dioxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-ylcarboxyloates （6d-e） by using excessive acid chlorides. The structures of 10 new compounds were determined by 1H NMR, 13C NMR, MS and HRMS, and the possible mechanism for the formation of unexpected products 5a--c and 6d-e was also proposed.

关键词： 9-(Hydroxyirnino)-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one oxime-ester N-(8-Chloro-4-methyl-2-oxo-2H-furo[2,3-h]chro-men-9-yl)amide 4-Methyl-2,9-dioxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-ylcarboxyloate

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