含α-氨基膦酸酯、芳香胺取代的氰基丙烯酸酯(酰胺)衍生物的合成与生物活性分析-农药学专业论文.docxVIP

贵州 贵州大学 2009 届硕士研究生毕业论文 PAGE PAGE 2 Abstract 2-Cyanoacrylate is a special type of compound known for its versatile biological activity and wide application in agricultural chemistry. In our previous work, a series of cyanoacrylate compounds incorporating different structural features of aromatic amines, chiral amines, phosphonyl units, and aminophosphonates was prepared, and their activities evaluated. The result showed that some of these compounds possessed good anti-virus activities. In order to design and synthesize cyanoacrylate derivatives with high bioactivity, in the current investigation, α-aminophosphonates bearing alkyloxyethyl and fluorine moieties were introduced into the parent scaffold of cyanoacrylate (cyanoacrylamide). Also, for further screening, aromatic amines and simple α-aminophosphonates were introduced into the cyanoacrylate unit. Starting from ethyl cyanoacetate (cyanoacetic acid), 31 title compounds were synthesized. The structures of all the compounds were confirmed by 1H NMR, 13C NMR, 31P NMR, IR and elemental analysis. To optimize the reaction conditions, the synthesis of compound 5-1 was carried out under different conditions of microwave irradiation. The best result was obtained at 100 °C and 140 W microwave power with a reaction time of 30 min. A comparison of the yields from the conventional and microwave-assisted syntheses was performed; the microwave-assisted synthesis resulted in a moderate improvement in the yield from 19.4 to 31.4 %, but the reaction time was significantly shortened from 12 h to 30 min. In conclusion, microwave assisted synthesis was environment-friendly, rapid and afforded the desired product in moderate yields with the formation of fewer byproducts. The result of bioassay showed that some target compounds have excellent anti-TMV activity. The derivatives 5-17 and 5-24 display appreciably higher activities against TMV, with the curative rates of 58.8 % and 60.0 % respectively while compounds 5-17 and 5-24