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Design, synthesis and insecticidal activity of biphenyl-diamide derivatives

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Chinese Chemical Letters 2016年第3期27卷 321-324页

作者： Ye Liu Chao Lei Xiao-Yong xu xu-sheng shao Zhong Li Shanghai Key Laboratory of Chemical Biology School of PharmacyEast China University of Science and Technology

Diamides acting on insect ryanodine receptors are an intensive research area now. In order to search for novel candidates, a series of diamides containing biphenyl substructure were designed and *** insecticidal activities against armyworms（Mythimna sepatara） and aphis（Aphis craccivora） were screened. The compounds with 3,5-dichloro-4-（1,1,2,2-tetrafluoroethoxy）phenyl substituent were found to be insecticidal to armyworms with the similar symptoms to poisoning by flubendiamide. In this research, we presented a novel type of diamide insecticide as a lead compound for further optimization.

关键词： Diamide Insecticide Ryanodine insecticide Biphenyl

Synthesis and insecticidal evaluation of phytoalexin phenalenones derivatives

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Chinese Chemical Letters 2017年第6期28卷 1228-1231页

作者： Ya-Nan Zhang Yi-An Feng Zhong Li xu-sheng shao Shanghai Key Laboratory of Chemical Biology School of Pharmacy East China University of Science and Technology Shanghai 20037 China

Phenalenone is a kind of defensive compound biosynthesized inside plants in response to the outside attack such as fungus and nematodes.A set of derivatives encompassing structural modifications on the privileged phenalenone scaffold were synthesized through introduction of phenyl and hydroxy!substitutes at 9-positon and 2-position and assessed their insecticidal activities against armyworm（Mythimna separata Walker） and cowpea aphids[Aphis craccivora）.No obvious insecticidal activities of the synthesized compounds were observed against *** of the 9-phenyl and 2-hydroxy substituted phenalenone analogues showed potential activities against cowpea aphids with 33%-41%mortality at 500 mg/L.

关键词： Phenalenones derivatives Insecticidal activities Structural modifications

Design,synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold

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Chinese Chemical Letters 2013年第8期24卷 673-676页

作者： Yin-Bo Chen Ji-Ling Li xu-sheng shao Xiao-Yong xu Zhong Li Shanghai Key Lab of Chemistry Biology School of PharmacyEast China University of Science and Technology

A series of novel anthranilic diamides with benzyl sulfide scaffold were synthesized,in which N-pyridylpyrazole moiety generally regarded as key pharmacophore was *** target compounds were characterized by ~1H NMR,^（13）C NMR,^（19）F NMR and *** preliminary bioassays indicated that half of the title compounds were endowed with good insecticidal activities against armyworm（Mythimna sepatara） at the concentration of 500 mg/L,Exhilaratingly,the synthesized compound 3a was also active against Tetranychus cinnabarinus at 100 mg/*** difference in activities between the target compounds was influenced by the substituents,which provided some hints for further investigation on structure modifications.

关键词： Anthranilic diamides Benzyl sulfide Synthesis Insecticidal activity

Synthesis and insecticidal evaluation of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives

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Chinese Chemical Letters 2016年第1期27卷 7-10页

作者： xuan-Qi Liu Ya-Qin Liu xu-sheng shao Zhi-Ping xu Xiao-Yong xu Zhong Li Shanghai Key Lab of Chemistry Biology School of Pharmacy East China University of Science and Technology Shanghai 200237 China Shanghai Collaborative Innovation Center for Biomanufacturing Technology Shanghai 200237 China

A series of novel tetrahydroimidazo[1,2-a]pyridine-5（1H）-one derivatives containing a electronegative pharmacophore（=CNO_2） were synthesized via practical aza-ene reaction and characterized by ~1H NMR,^（13）C NMR,^（19）F NMR and HRMS. Preliminary bioassays showed that some of the target compounds exhibited good insecticidal activity against brown planthopper（Nilaparvata lugens） and cowpea aphids（Aphis craccivora） at 500 mg L^（-1）. Among them, compound 11 h was active against brown planthopper at100 mg L^（-1）. The insecticidal activities varied significantly depending on the types and patterns of the substituents, which provided guidance for further investigation on structure modifications.

关键词： Neonicotinoids Tetrahydroimidazo[1,2-a]pyridin-5(1H) one Configuration Insecticidal activity

Facile three-component synthesis and insecticidal evaluation of hexahydroimidazo[1,2-a]pyridine derivatives

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Chinese Chemical Letters 2015年第1期26卷 1-5页

作者： Ye-Feng Fan Wen-Wen Zhang xu-sheng shao Zhi-Ping xu Xiao-Yong xu Zhong Li Shanghai Key Lab of Chemistry Biology School of PharmacyEast China University of Science and Technology Shanghai Collaborative Innovation Center for Biomanufacturing Technology

A series of new hexahydroimidazo[1,2-a]pyridine derivatives were synthesized via convenient and practical three-component reactions. Preliminary bioassays showed that majority of the target compounds exhibited moderate to excellent insecticidal activity against cowpea aphids （Aphis craccivora）. Among them, compound 91 demonstrated significant activity with LCso value of 0.00918 mmol/L which was about 3.8-fold higher than that of imidacloprid （IMI）. Furthermore, the study of stereostructure-activity relationship of four isomers of 9k indicated that configuration played a key role in insecticidal activity of these compounds.

关键词： Neonicotinoids Hexahydroimidazo[ 1,2-a]pyridine Three-component reaction Configuration Insecticidal activity

Bioactive conformation analysis of anthranilic diamide insecticides:DFT-based potential energy surface scanning and 3D-QSAR investigations

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Chinese Chemical Letters 2015年第6期26卷 662-666页

作者： Dan-Ping Jiang Cheng-Chun Zhu xu-sheng shao Jia-Gao Cheng Zhong Li Shanghai Key Laboratory of Chemical Biology School of PharmacyEast China University of Science and Technology Shanghai Collaborative Innovation Center for Biomanufacturing Technology

Anthranilic diamides are fasting growing class insecticides in modern crop protection for their high activity, low ecotoxicity, and broad insecticidal spectra. However. the bioactive conformations of anthranilic diamides are still unclear until now. In the present study, DFT-based potential energy surface scanning was used to detect the low energy conformations of chlorantraniliprole, then were used respectively in the structure alignment for a series of anthranilic diamide compounds followed by detailed CoMFA and CoMSIA analyses. Finally, the bioactive conformations of anthranilic diamide insecticides were revealed from a series of low energy conformations, which might provide some clues for future insecticide design.

关键词： Bioactive conformation Anthranilic diamides Potential energy surface scanning 3D-QSAR

Design,synthesis and insecticidal activity of spiro heterocycle containing neonicotinoid analogs

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Chinese Chemical Letters 2014年第2期25卷 197-200页

作者： Nan-Yang Chen Li-Ping Ren Min-Ming Zou Zhi-Ping xu xu-sheng shao Xiao-Yong xu Zhong Li Shanghai Key Laboratory of Chemical Biology School of PharmacyEast China University of Science and Technology

Spiro heterocycles frequently occur in bioactive molecules. In the pursuit of neonicotinoids with spiro hererocycles, three types of novel neonicotinoids with spirobenzofuranone, spirooxindole or spiroacenaphythylenone framework were designed and synthesized. Insecticidal evaluation showed that some of spirobenzofuranone containing neonicotinoids exhibited moderate activity against cowpea aphid, armyworm or brown planthopper.

关键词： Neonicotinoid Spiro heterocycle Activity Insecticide

Azopyridine-imidacloprid derivatives as photoresponsive neonicotinoids

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Chinese Chemical Letters 2016年第5期27卷 635-639页

作者： Shen Li Run-Jiang Song Dong-Hui Wang xue Tian xu-sheng shao Zhong Li Shanghai Key Laboratory of Chemical Biology School of Pharmacy East China University of Science and Technology Shanghai 200237 China College of Life Science Perking University Beijing 100871 China

A series of imidacloprid derivatives containing an azopyridine motif as a photoswitchable functional group were designed and synthesized. The new version of photoresponsive imidacloprid analogues showed improved solubility in comparison with their azobenzene analogues. 1.2 to 2-fold activity difference was observed for these azopyridine-imidacloprids against house fly （Musca domestica） and cowpea aphid （Aphis craccivora） upon irradiation.

关键词： Azopyridine Photoresponsive Imidacloprid Solubility Insecticide

A novel and facile synthesis of 2-oxo-1,2-dihydropyridine-fused 1,3-diazaheterocycles via heterocyclic ketene aminals and Konevenagel adducts formed by phthalic anhydride and ethyl cyanacetate

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Chinese Chemical Letters 2014年第12期25卷 1515-1519页

作者： Min-Ming Zou Feng-Juan Zhu xue Tian Li-Ping Ren xu-sheng shao Zhong Li Shanghai Key Laboratory of Chemical Biology School of PharmacyEast China University of Science and Technology

An efficient synthetic pathway to 2-oxo-1,2-dihydropyridine-fused 1,3-diaza heterocycles from heterocyclic ketene aminals,phathalic anhydride and ethyl cyanacetate was *** protocol involved aza-ene reaction/imine-enam... 详细信息

关键词： Heterocyclic ketene aminals 2-Oxo-1 2-dihydropyridine 1 3-Diazaheterocycle Synthesis