RESUMO
In continuation of our program aimed at the development of natural product-based pesticidal agents, a series of matrinic amide derivatives containing 1,3,4-thiadiazole scaffold were prepared, and their insecticidal and acaricidal activities were evaluated against Mythimna separata and Tetranychus cinnabarinus. Some compounds exhibited potent insecticidal and acaricidal activities. It suggested that R1 as a nitro group and R2 as a fluorine atom, were important for the insecticidal activity; R1 as the electron-donating groups and R2 as the methyl group, were necessary for the acaricidal activity.
Assuntos
Acaricidas/farmacologia , Alcaloides/farmacologia , Amidas/farmacologia , Inseticidas/farmacologia , Mariposas/efeitos dos fármacos , Quinolizinas/farmacologia , Tetranychidae/efeitos dos fármacos , Tiadiazóis/farmacologia , Acaricidas/síntese química , Acaricidas/química , Alcaloides/síntese química , Alcaloides/química , Amidas/síntese química , Amidas/química , Animais , Relação Dose-Resposta a Droga , Inseticidas/síntese química , Inseticidas/química , Estrutura Molecular , Quinolizinas/síntese química , Quinolizinas/química , Relação Estrutura-Atividade , Tiadiazóis/química , MatrinasRESUMO
A series of 2'(2',6')-(di)halogeno-isoxazolopodophyllic acids-based esters, and oxime sulfonates of 2'(2',6')-(di)halogenopodophyllones were prepared by structural modifications of podophyllotoxin as insecticidal agents against Mythimna separata Walker. It was found that when 2'(2',6')-(di)halogenopodophyllones or 2'(2',6')-(di)chloropicropodophyllones reacted with hydroxylamine hydrochloride, the desired products were related with the configuration of their lactones. Three key single-crystal structures of Ie, IIe and IIIb were determined by X-ray diffraction. Especially compounds IIc and Vc showed the highest insecticidal activity. Moreover, some interesting results of structure-insecticidal activity relationships of tested compounds were also observed.