2-取代-4-氯-5-芳基-2H-1,2,3-三唑类化合物的合成及其生物活性

Synthesis and Biological Activity of 2-substitued-4-chloro-5-aryl-2H-1,2,3-triazole Derivatives

摘要:

为发现杀菌活性高、抑菌谱广的新化合物，以芳醛、硝基甲烷及叠氮化钠为起始原料，经环化、氯化、烃化反应合成了15个2-取代-4-氯-5-芳基-2H-1,2,3-三唑类新化合物，目标物的分子结构经核磁共振谱、质谱和元素分析进行了确证。采用菌丝生长速率测定法，在25 mg/L的测试浓度下，目标化合物对小麦赤霉病菌、辣椒疫霉病菌、烟草赤星病菌、黄瓜灰霉病菌、水稻纹枯病菌及油菜菌核病菌6种作物病菌进行了离体抑菌活性试验。初步的抑菌活性测试结果表明：化合物4d对小麦赤霉病菌、黄瓜灰霉病菌及油菜菌核病菌的抑制率分别为70.4%、74.1%和72.9%，化合物4k对黄瓜灰霉病菌及油菜菌核病菌的抑制率分别为87.0%及84.7%。4d对辣椒疫霉病菌的抑制率为61.4%，高于商品化品种苯醚甲环唑的42.5%。

Abstract:

In order to discover new compounds with high bactericidal activity and broad inhibition, fifteen series of new 2-substituted-4-chloro-5-aryl-2H-1,2,3-triazole derivatives were synthesized using aryl aldehyde, nitromethane and sodium azide as starting materials through cyclization, chlorination and alkylation reactionin. The structures of title compounds were confirmed by 1H NMR, 13C NMR, mass spectra and elemental analyses. The in vitro antifungal activities of target compound were evaluated against six phytopathogenic fungi (Gibberella zeae, Phytophythora capsici, Alternaria alternate, Botrytis cinerea, Rhizoctonia solani and Sclerotonia sclerotiorum) using the mycelium growth rate method under the test concentration of 25 mg/L. The results of bioassay showed that some compounds exhibited excellent fungicidal activities. For example, the inhibition rates of compound 4d against Gibberella zeae, Botrytis cinerea and Sclerotonia sclerotiorum were 70.4%, 74.1% and 72.9%, respectively. The inhibition rates of compound 4k against Botrytis cinerea and Sclerotonia sclerotiorum were 87.0% and 84.7% respectively. The inhibition rate of 4d against Phytophythora capsici was 61.4%, which was higher than that of commercial difenoconazole 42.5%.