Paper
Synthesis and biological activity of 4-methyl-1,2,3-thiadiazole-5-carboxylates
Published 2010 · Song Hai-bin
Chinese Journal of Pesticide Science
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Abstract
Heterocyclic compounds had various biological activities,in order to explore novel elicitors with a broad spectrum and highly systemic acquired resistance,a series of 4-methyl-1,2,3-thiadiazole-5-carboxylates were synthesized by using 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride and substituted hydroxyl aromatic compounds as reactants.These reactions were conducted in dichloromethane at room temperature and using triethylamine as acid binding agent.All synthesized compounds including 9 new structures were confirmed by 1H NMR,IR and HRMS.Crystal structure of 2g was cultured and characterized by X-ray crystal diffraction method to validate the detailed chemical structure for this kind of compounds.Bioassay indicated that some compounds possessed obvious fungicidal activity at a concentration of 50 μg/mL.Among these compounds,2c,2n and 2o possessed a broad spectrum of fungicidal activity and EC50 value of these compounds ranged from 3.46 to 23.30 μg/mL.Antivirus activity screening indicated that some compounds possessed good anti-TMV activity and most compounds displayed good inactivation activity against TMV.Moreover,compounds including 2a,2c,2d,2e,2f,2g,2l and 2o exhibited good systemic acquired resistance for tobacco against TMV as compared with positive control agents.
The synthesized 4-methyl-1,2,3-thiadiazole-5-carboxylates show promising fungicidal and anti-TMV properties, with some showing good systemic acquired resistance for tobacco against TMV.
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