Synthesis, fungicidal activity, and 3D-QSAR of pyridazinone-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles
| Autor: | Gui-Yu Jin, Xia-Juan Zou, Luhua Lai, Zu-Xing Zhang |
|---|---|
| Rok vydání: | 2002 |
| Předmět: |
Quantitative structure–activity relationship
Oxadiazoles biology Molecular Structure Stereochemistry Chemistry Biological activity General Chemistry Ring (chemistry) biology.organism_classification Chemical synthesis Fungicides Industrial Pyridazines Wheat leaf rust Structure-Activity Relationship Thiadiazoles Structure–activity relationship Puccinia recondita General Agricultural and Biological Sciences |
| Zdroj: | Journal of agricultural and food chemistry. 50(13) |
| ISSN: | 0021-8561 |
| Popis: | A series of novel 5-[1-aryl-1,4-dihydro-6-methylpyridazin-4-one-3-yl] -2-arylamino-1,3,4-oxadiazoles, fungicidally active, were synthesized based on bioisosterism and tested in vivo against wheat leaf rust, Puccinia recondita. These compounds were shown to be fungicidally active, and their activity was influenced by the nature of the substituents. By using the three-dimensional quantitative structure-activity relationships (3D-QSAR) method of comparative molecular field analysis (CoMFA), we have studied the structure and activity relationship of the compounds containing both pyridazinone-substituted 1,3,4-thiadiazoles and pyridazinone-substituted 1,3,4-oxadiazoles. The 3D-QSAR modes gave good correlation between the variations on percent inhibition and the steric-electrostatic properties. The results are consistent with a common mode of action for the pyridazinone-substituted 1,3,4-thiadiazoles and the pyridazinone-substituted 1,3,4-oxadiazoles, which further confirms that the 1,3,4-oxadiazole ring is a bioisosteric analogue of the 1,3,4-thiadiazole ring. These offer important structural insights into designing highly active compounds prior to their synthesis. |
| Databáze: | OpenAIRE |
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