【摘要】：1,4-戊二烯-3-酮類似物與姜黃素結(jié)構(gòu)相似,穩(wěn)定性優(yōu)于姜黃素,具有抗病毒、抗氧化、抗炎、抗癌、殺蟲、抑菌、抗腫瘤、除草等多種生物活性;此外,現(xiàn)如今,含氮雜環(huán)化合物在農(nóng)藥的研究與開發(fā)中具有十分重要的地位,引入雜環(huán)化合物往往顯著改善其理化性質(zhì)及其生物活性;肟酯類化合物是一類重要的活性化合物,具有殺蟲活性、抑菌、抗病毒、除草等生物活性,且大多數(shù)肟酯化合物有高效、低毒、低殘留等優(yōu)點,因此,含肟酯基團類化合物長期以來受到廣泛的研究。針對以上現(xiàn)狀,為了尋找具有較高活性的化合物,本課題采用活性基團拼接原理,將雜環(huán)和肟脂引入1,4-戊二烯-3-酮結(jié)構(gòu)中,通過醚化、肟化、酯化合成了40個含雜環(huán)1,4-戊二烯-3-酮肟脂類化合物,其結(jié)構(gòu)經(jīng)過1H NMR、13C NMR、IR及HRMS進行表征。采用生長速率法對目標化合物進行抑真菌活性測試,在藥劑濃度為50μg/m L時,結(jié)果表明該類部分化合物具有一定的抑菌活性。其中化合物I23、II3、II8、II9對小麥赤霉病菌(G.zeae)的抑制率分別為42.8、45.2、45.6、48.3%,接近對照藥劑醚菌酯54.3%;化合物I19、I26、II2、II12對黃瓜灰霉病菌(B.Cinerea)的抑制率分別為51.2、63.6、52.4、51.4%,低于對照藥劑醚菌酯70.3%;化合物II4對水稻紋枯病菌(R.solani)的抑制率為50.9%,但仍低于對照藥劑醚菌酯63.6%。采用濁度法對目標化合物進行抑細菌活性測試,在藥劑濃度為200μg/m L和100μg/mL時,化合物具有一定的抑菌活性。其中化合物在200μg/mL的抑制濃度下,化合物I21、II7、II11對水稻白葉枯病菌(X.oryzae)的抑制率分別為89.4、93.1、79.3%,高于對照藥劑葉枯唑77.5%;在100μg/mL的抑制濃度下,化合物I20、II7對水稻白葉枯病菌(X.oryzae)的抑制率分別為68.3、85.2%,高于對照藥劑葉枯唑56.4%;在200μg/m L的抑制濃度下,化合物I22對煙草青枯病菌(R.solanacearum)的抑制率為92.4%,略低于對照藥劑94.1%;在200μg/mL的抑制濃度下,化合物I3、I14、I16、I18、II1、II2、II7對柑橘潰瘍病菌(X.citri)的抑制率分別為94.5、94.5、89.0、92.1、86.8、81.3、81.2%,高于對照藥劑葉枯唑80.4%,在100μg/mL的抑制濃度下,化合物I3、I14、I16、I18、II7對柑橘潰瘍病菌(X.citri)的抑制率分別為81.8、83.4、80.9、76.8、67.2%,高于對照藥劑葉枯唑63.2%。采用半葉枯斑法對目標化合物進行了抗煙草花葉病毒(TMV)的活性測定,測試結(jié)果表明:部分化合物在500μg/m L的濃度下對煙草花葉病毒均有較好的抑制作用。化合物I5、I12、II1的治療活性分別為58.8、59.2、53.7%,高于對照藥劑寧南霉素51.8%;化合物I20、I25、II4、II6、II7的保護活性分別為65.1%、66.3、62.2、64.9、64.8%,與對照藥劑寧南霉素(65.7%)相當;化合物I5的鈍化活性為70.8%,低于對照藥劑寧南霉素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，

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