Studies On The Synthesis And Biological Activity Of Two Categories Of Multiarylmines And Their Amide Derivatives

Amide herbicides are a class of multiple-target directed herbicides and play an important role in nowadays commercial agrochemicals.The herbicidal mechanisms of amide herbicides mainly include the inhibition of the biosyntheses of fat and fatty acids, inhibition of the electron transfer in photosynthesis,interference of the the biosynthesis of plant proteins and cell division,affection of the integration of cellular membrane,and probable inhibition of plant respiration,etc.In our previous work,we obtained a series of hits concerning the lead compounds targeting D1 protease.Among them,two classes of multiarylmines and their amide derivatives were chosen as the lead compounds for chemical synthesis,and these compounds were theoretically predicted to have high inhibitive effects to D1 protease.D1 protease is the carboxyl terminal processing enzyme for precursor D1 protein.Its role is cutting off the C-terminal extension of polypeptide of the precursor D1 protein to form mature D1 protein,which is responsible for the assembly of the photosystemâ…¡in plants.In recent years,D1 protease has been found as one novel herbicidal target, because of its low content comparing with D1 protein in plant,which is the target of commercially prevalent herbicides in present,such as Simagine,Atrazine,Diuron,etc. Therefore it is very important to develop novel herbicides targeting D1 protease.In this thesis,two categories of multiarylmines and their amide derivatives as lead compounds have been rationally designed and synthesized,and their in vivo and in vitro bioactivities were investigated.The main contents are listed as the following:1.Synthesized(z)-3-(4-aminophenyl)-2-phenylacrylonnitrile and 4 of its amide derivatives,(z)-3-(3-aminophenyl)-2-phenylacrylonnitrile and 8 of its amide derivatives, those 12 amide derivatives have never been reported in literature so far,and their structure have been affirmed by ¹HNMR,GC-MS,IR,etc;2.Synthesized 3-(4-aminophenyl)-2-phenylpropanoic acid and one of its amide derivative,which has never appeared in the present literature and their structure have been affirmed by ¹H NMR,MS,IR,etc;3.A primary test of bioactivities in vivo has been carried out on all the synthesized target compounds,through which the author discovered that at 100 ppm most of the target compounds exert an obvious prohibition effect on the growth of the dicotyledon cole and monocotyledon barnyard grass,moreover,when the thickness is at 10ppm,the inhibitive effects reduced to between 20%and 60%.Meanwhile,the sterilization activity test of these compounds has shown that some compounds have preferable inhibitive effects on some plant pathogen. 4.With D1 protease as the drone,precursor D1 protein C-terminal 24 peptide as simulation substrates,chromatogram the author has measured the prohibition activity of two carboxylic acid amides synthesized in this research on D1 protease,and affirmed that the prohibition constants K_i were 8.8μmol.L^-1and 5.2μmol.L^-1.It proved that the weeding activity of these carboxylic acid amides originated from the prohibition activity towards D1 protease in the plant.