含杂环1,4-戊二烯-3-酮肟酯类化合物的合成及其生物活性研究
发布时间：2018-08-14 17:15
【摘要】：1,4-戊二烯-3-酮类似物与姜黄素结构相似,稳定性优于姜黄素,具有抗病毒、抗氧化、抗炎、抗癌、杀虫、抑菌、抗肿瘤、除草等多种生物活性;此外,现如今,含氮杂环化合物在农药的研究与开发中具有十分重要的地位,引入杂环化合物往往显著改善其理化性质及其生物活性;肟酯类化合物是一类重要的活性化合物,具有杀虫活性、抑菌、抗病毒、除草等生物活性,且大多数肟酯化合物有高效、低毒、低残留等优点,因此,含肟酯基团类化合物长期以来受到广泛的研究。针对以上现状,为了寻找具有较高活性的化合物,本课题采用活性基团拼接原理,将杂环和肟脂引入1,4-戊二烯-3-酮结构中,通过醚化、肟化、酯化合成了40个含杂环1,4-戊二烯-3-酮肟脂类化合物,其结构经过1H NMR、13C NMR、IR及HRMS进行表征。采用生长速率法对目标化合物进行抑真菌活性测试,在药剂浓度为50μg/m L时,结果表明该类部分化合物具有一定的抑菌活性。其中化合物I23、II3、II8、II9对小麦赤霉病菌(G.zeae)的抑制率分别为42.8、45.2、45.6、48.3%,接近对照药剂醚菌酯54.3%;化合物I19、I26、II2、II12对黄瓜灰霉病菌(B.Cinerea)的抑制率分别为51.2、63.6、52.4、51.4%,低于对照药剂醚菌酯70.3%;化合物II4对水稻纹枯病菌(R.solani)的抑制率为50.9%,但仍低于对照药剂醚菌酯63.6%。采用浊度法对目标化合物进行抑细菌活性测试,在药剂浓度为200μg/m L和100μg/mL时,化合物具有一定的抑菌活性。其中化合物在200μg/mL的抑制浓度下,化合物I21、II7、II11对水稻白叶枯病菌(X.oryzae)的抑制率分别为89.4、93.1、79.3%,高于对照药剂叶枯唑77.5%;在100μg/mL的抑制浓度下,化合物I20、II7对水稻白叶枯病菌(X.oryzae)的抑制率分别为68.3、85.2%,高于对照药剂叶枯唑56.4%;在200μg/m L的抑制浓度下,化合物I22对烟草青枯病菌(R.solanacearum)的抑制率为92.4%,略低于对照药剂94.1%;在200μg/mL的抑制浓度下,化合物I3、I14、I16、I18、II1、II2、II7对柑橘溃疡病菌(X.citri)的抑制率分别为94.5、94.5、89.0、92.1、86.8、81.3、81.2%,高于对照药剂叶枯唑80.4%,在100μg/mL的抑制浓度下,化合物I3、I14、I16、I18、II7对柑橘溃疡病菌(X.citri)的抑制率分别为81.8、83.4、80.9、76.8、67.2%,高于对照药剂叶枯唑63.2%。采用半叶枯斑法对目标化合物进行了抗烟草花叶病毒(TMV)的活性测定,测试结果表明:部分化合物在500μg/m L的浓度下对烟草花叶病毒均有较好的抑制作用。化合物I5、I12、II1的治疗活性分别为58.8、59.2、53.7%,高于对照药剂宁南霉素51.8%;化合物I20、I25、II4、II6、II7的保护活性分别为65.1%、66.3、62.2、64.9、64.8%,与对照药剂宁南霉素(65.7%)相当;化合物I5的钝化活性为70.8%,低于对照药剂宁南霉素95.8%。
[Abstract]:Similar to curcumin, its stability is superior to that of curcumin. It has many biological activities, such as antivirus, antioxidation, anti-inflammation, anti-cancer, insecticidal, bacteriostatic, anti-tumor, herbicide and so on. Heterocyclic compounds containing nitrogen play an important role in the research and development of pesticides. The introduction of heterocyclic compounds often improves their physical and chemical properties and biological activities, oxime esters are an important class of active compounds with insecticidal activities. Most of the oxime ester compounds have the advantages of high efficiency, low toxicity, low residue and so on. Therefore, the oxime ester group compounds have been widely studied for a long time. In order to find the compounds with high activity, the heterocyclic and oxime lipids were introduced into the structure of 1 ~ 4- pentadiene-3-one by etherification and oximation. Forty heterocyclic 1-pentadiene-3-ketoxime lipids were synthesized by esterification. Their structures were characterized by 1H NMR-13C NMR-IR and HRMS. The growth rate method was used to test the fungicidal activity of the target compounds. The results showed that some of the compounds had certain bacteriostatic activity at the concentration of 50 渭 g / mL. The inhibition rates of compound I23, I23, II3, II8, II9, on wheat scab bacteria (G.zeae) were 42.8N 45.2N 45.6N 48.3s, which were close to that of the control agent ether ester 54.3.The inhibition rate of compound I19C I26I2H2CY II12 on cinerea (B.Cinerea) was 51.23.62.42.40.1.4, which was lower than that of the control agent, Ether ester 70.3.The compound I19C was lower than that of the control agent, Ether ester 70.3.The inhibition rate of compound I23C I26I2CY IIII12 on Cucumber Gray Mould (B.Cinerea) was 51.23.62.40.44%, respectively. The inhibition rate of R.solani was 50.9%, but still lower than that of the control group (63.6%). The bacteriostatic activity of the target compound was tested by turbidimetric method. When the drug concentration was 200 渭 g / mL and 100 渭 g/mL, the compound had certain bacteriostatic activity. At the inhibitory concentration of 200 渭 g/mL, the inhibitory rates of compound I _ (21) I _ (7) I _ (11) on bacterial blight bacteria (X.oryzae) in rice were 89.4 ~ 93.1% and 79.3%, respectively, which were higher than those of the control, and at the inhibitory concentration of 100 渭 g/mL, the inhibition rate of I21- 鈪，
本文编号：2183553
[Abstract]:Similar to curcumin, its stability is superior to that of curcumin. It has many biological activities, such as antivirus, antioxidation, anti-inflammation, anti-cancer, insecticidal, bacteriostatic, anti-tumor, herbicide and so on. Heterocyclic compounds containing nitrogen play an important role in the research and development of pesticides. The introduction of heterocyclic compounds often improves their physical and chemical properties and biological activities, oxime esters are an important class of active compounds with insecticidal activities. Most of the oxime ester compounds have the advantages of high efficiency, low toxicity, low residue and so on. Therefore, the oxime ester group compounds have been widely studied for a long time. In order to find the compounds with high activity, the heterocyclic and oxime lipids were introduced into the structure of 1 ~ 4- pentadiene-3-one by etherification and oximation. Forty heterocyclic 1-pentadiene-3-ketoxime lipids were synthesized by esterification. Their structures were characterized by 1H NMR-13C NMR-IR and HRMS. The growth rate method was used to test the fungicidal activity of the target compounds. The results showed that some of the compounds had certain bacteriostatic activity at the concentration of 50 渭 g / mL. The inhibition rates of compound I23, I23, II3, II8, II9, on wheat scab bacteria (G.zeae) were 42.8N 45.2N 45.6N 48.3s, which were close to that of the control agent ether ester 54.3.The inhibition rate of compound I19C I26I2H2CY II12 on cinerea (B.Cinerea) was 51.23.62.42.40.1.4, which was lower than that of the control agent, Ether ester 70.3.The compound I19C was lower than that of the control agent, Ether ester 70.3.The inhibition rate of compound I23C I26I2CY IIII12 on Cucumber Gray Mould (B.Cinerea) was 51.23.62.40.44%, respectively. The inhibition rate of R.solani was 50.9%, but still lower than that of the control group (63.6%). The bacteriostatic activity of the target compound was tested by turbidimetric method. When the drug concentration was 200 渭 g / mL and 100 渭 g/mL, the compound had certain bacteriostatic activity. At the inhibitory concentration of 200 渭 g/mL, the inhibitory rates of compound I _ (21) I _ (7) I _ (11) on bacterial blight bacteria (X.oryzae) in rice were 89.4 ~ 93.1% and 79.3%, respectively, which were higher than those of the control, and at the inhibitory concentration of 100 渭 g/mL, the inhibition rate of I21- 鈪，
本文编号：2183553
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