氰基苯氧氟酰胺的合成及其抗柑橘霉菌活性

Synthesis of cyanophenyloxyfluoroamide and its bacteriostatic activity against citrus fungus

摘要:

为了挖掘新型的抗柑橘霉菌活性先导物，以邻羟基苯甲腈、溴氟乙酸乙酯和胺为原料，设计、合成了15个氰基苯氧氟酰胺化合物，通过1HNMR、13CNMR和MS鉴定了产物结构；采用菌丝生长速率法测定了这些化合物对柑橘青霉菌（Penicillium italicum）和绿霉菌（Penicillium digitatum）的抑制活性。结果表明，这些化合物对所测菌种均有一定的抑制活性。其中，化合物Ⅰa〔2-（2-氰基苯氧基）-2-氟-N-苯基乙酰胺〕、Ⅰf〔N-（2-噻唑基）-2-（2-氰基苯氧基）-2-氟乙酰胺〕等6个化合物在200 mg/L质量浓度下对两种菌的抑制活性达到80% ~ 100%；化合物Ⅰh的抗菌活性最高，在50 mg/L质量浓度下对青霉菌和绿霉菌的抑制率分别为60.96%和53.95%，25 mg/L质量浓度下的抑制率也有30%以上。2-氰基苯氧氟酰胺化合物的抗柑橘青、绿霉菌活性均优于2,4-D（2,4-二氯苯氧乙酸）。

Abstract:

In order to explore new lead compounds against Penicillium italicum(PI) and Penicillium digitatum(PD) on citrus, fifteen 2-(2-cyanophenoxy)-2-fluoroacetamides were designed and synthesized using salicylonitrile, ethyl bromofluoroacetate, and amines as the main starting materials. Their structures were confirmed by 1HNMR, 13CNMR and MS. The antibacterial activity of these compounds against PI and PD was studied by the mycelial growth rate method. The results showed that these compounds had certain antibacterial activity against the tested strains. Among them, six compounds such as Ⅰa[ 2-(2-cyanophenoxy)-2-fluoro-N-phenylacetamide],Ⅰf[2-(2-cyanophenoxy)-2-fluoro-N-(thiazol-2-yl)acetamide] have 80% ~ 100% inhibitory activity against the two bacteria at the mass concentration of 200 mg/L. The antibacterial activity of compound Ⅰh is the best among all compounds. At the mass concentration of 50 mg/L, it’s inhibition rates of PI and PD are 60.96% and 53.95%, respectively. The inhibitions rates are more than 30% at the mass concentration of 25 mg/L. The activity of 2-(2-cyanophenoxy)-2-fluoroacetamides against tested strains is better than 2,4-D(2,4-Dichlorophenoxyacetic acid).