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

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.

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

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.

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

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.

Design, synthesis and insecticidal activity of biphenyl-diamide derivatives

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.

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

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.

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

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.

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

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.

Synthesis and insecticidal evaluation of phytoalexin phenalenones derivatives

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.

Azopyridine-imidacloprid derivatives as photoresponsive neonicotinoids

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.

Synthesis and insecticidal activities of 1,8-naphthyridine derivatives

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.