Spiro heterocycles frequently occur in bioactive molecules. In the pursuit of neonicotinoids with spiro hererocycles, three types of novel neonicotinoids with spirobenzofuranone, spirooxindole or spiroacenaphythylenon...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.展开更多
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 moderat...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.展开更多
A series of novel anthranilic diamides with benzyl sulfide scaffold were synthesized,in which N-pyridylpyrazole moiety generally regarded as key pharmacophore was abandoned.The target compounds were characterized by ~...A series of novel anthranilic diamides with benzyl sulfide scaffold were synthesized,in which N-pyridylpyrazole moiety generally regarded as key pharmacophore was abandoned.The target compounds were characterized by ~1H NMR,^(13)C NMR,^(19)F NMR and HRMS.The 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/L.The difference in activities between the target compounds was influenced by the substituents,which provided some hints for further investigation on structure modifications.展开更多
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 synthesized.Their inse...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 synthesized.Their 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.展开更多
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 diami...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.展开更多
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 NM...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.展开更多
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 phen...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 armyworm.Some of the 9-phenyl and 2-hydroxy substituted phenalenone analogues showed potential activities against cowpea aphids with 33%-41%mortality at 500 mg/L.展开更多
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 solub...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.展开更多
1,8-Naphthyridines(NAP) are biological important scaffolds in bioactive molecules design. By hybrid of NAP with neonicotinoid core structure, nine novel NAP derivatives were synthesized and subjected to insecticidal...1,8-Naphthyridines(NAP) are biological important scaffolds in bioactive molecules design. By hybrid of NAP with neonicotinoid core structure, nine novel NAP derivatives were synthesized and subjected to insecticidal activities evaluation. Some of the compounds showed excellent insecticidal activity against cowpea aphids(Aphis craccivora) with LC_(50) values ranging from 0.011 mmol/L to 0.067 mmol/L. The results indicated that 1,8-naphthyridine can be used as insecticidal structure for further modification.展开更多
基金financial supported by National Basic Research Program of China(973 Program,No.2010CB126100)National High Technology Research Development Program of China(863 Program,No.2011AA10A207)+4 种基金Key Projects in the National Science & Technology Pillar Program(No.2011BAE06B05)National Natural Science Foundation of China(No.21372079)Shanghai Education Committee(No.12ZZ057)the Fundamental Research Funds for the Central Universitiespartly supported by Australia DC Foundation
文摘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.
基金supported by National Key Technology R&D Program of China(No.2011BAE06B01)
文摘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.
基金supported by National Basic Research Program of China(973 Program,No.2010CB126100)National High Technology Research and Development Program of China (863 Program,No.2011AA10A207)supported by National Key Technology R&D Program of China(No. 2011BAE06B01)
文摘A series of novel anthranilic diamides with benzyl sulfide scaffold were synthesized,in which N-pyridylpyrazole moiety generally regarded as key pharmacophore was abandoned.The target compounds were characterized by ~1H NMR,^(13)C NMR,^(19)F NMR and HRMS.The 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/L.The difference in activities between the target compounds was influenced by the substituents,which provided some hints for further investigation on structure modifications.
文摘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 synthesized.Their 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.
基金the financial support from the National Key Technology R&D Program of China (No.2011BAE06B05)
文摘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.
基金financial supported by National High Technology Research Development Program of China (863 Program, No. 2011AA10A207)National Natural Science Foundation of China (Nos. 21472046, 21372079)+2 种基金Shanghai Pujiang Program (No. 14PJD012)the Fundamental Research Funds for the Central Universities (No. 222201414015)partly supported by Australia DC Foundation
文摘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.
基金financial supported by National Natural Science Foundation of China(No.21372079)National High Technology Research Development Program of China(863 Program,No. 2011AA10A207)+3 种基金Shanghai Pujiang Program(No.14PJD012)Key Projects in the National Science & Technology Pillar Program(No. 2011BAE06B05)the Fundamental Research Funds for the Central Universitiespartly supported by Australia DC Foundation
文摘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 established.This protocol involved aza-ene reaction/imine-enamine tautomerization/enamine-ester exchange/ring-opening reaction sequence.
基金financial supported by National Natural Science Foundation of China(Nos.21472046,21372079)Science and Technology Commission of Shanghai Municipality(No.16391902300)
文摘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 armyworm.Some of the 9-phenyl and 2-hydroxy substituted phenalenone analogues showed potential activities against cowpea aphids with 33%-41%mortality at 500 mg/L.
基金financial supported by National Natural Science Foundation of China (Nos. 21372079, 21472046)Shanghai Pujiang Program (No. 14PJD012)the Fundamental Research Funds for the Central Universities (No. 222201414015)
文摘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.
基金financial supported by National Natural Science Foundation of China(Nos.21372079,21472046)Shanghai Pujiang Program(No.14PJD012)
文摘1,8-Naphthyridines(NAP) are biological important scaffolds in bioactive molecules design. By hybrid of NAP with neonicotinoid core structure, nine novel NAP derivatives were synthesized and subjected to insecticidal activities evaluation. Some of the compounds showed excellent insecticidal activity against cowpea aphids(Aphis craccivora) with LC_(50) values ranging from 0.011 mmol/L to 0.067 mmol/L. The results indicated that 1,8-naphthyridine can be used as insecticidal structure for further modification.