Synthesis Of A Series Of Maleimide And Comparion Of Their Antimicrobial Activities

Plant diseases caused by plant pathogenic fungi have resulted in large harm to the agriculture in every country.Sclerotinia sclerotiorum?Rhizoctonia solani and Botrytis cinerea,as two representatives of plant pathogenic fungi with a wide host range,complex origins,latent infection and strong saprophytism,are high-risk plant pathogen.Unfortunately,as the extensive use of the present fungicides,these pathogens exert resistance in some degree.In this case,developing novel,highly effective and structurally concise antifungal agents with low toxicities is an urgently challenging and especially significant task to control crop diseases.In the previous study,it has been reported that natural products with maleic anhydride structure or maleimide structure have high biological activities,but there are few species of natural maleimides.So in this paper,4-tert-butylphenyl methanamine?4-?4-methylphenoxy?benzylamine?2,3-dichloro-4-hydroxyphenyl?phenyldiazene and seven different maleic anhydride was selected as substrate,then malemides were synthesized by acetic acid method.By the time,we modify the compounds with maleic anhydride,long carbon chain was introduced to it.At last,malemides were synthesized by methanol solution of sodium methoxide and characterized by ¹H NMR and ESI-MS.There were 28kinds of malemides and the in-vitro antifungal activities studies against Sclerotinia sclerotiorum?Rhizoctonia solani and Botrytis cinerea were preliminary investigated by the mycelium growth rate method.The results showed that the new of maleimides had no obviously inhibition on S.sclerotiorum,R.solani and B.cinerea,but we expanded the compound library.Thenwefoundthatmaleimidessynthesizedby?2,3-dichloro-4-hydroxyphenyl?phenyldiazene had interesting inhibitory with S.sclerotiorum,Rhizoctonia solani and B.cinerea.6 of 28compounds??-1,?-1,?-3,?-4,?-7 and?-8?had stronger inhibitory potency(EC₅₀<10?g/mL).Besides,5 of 28 compounds??-1,?-1,?-3,?-4 and?-5?were more effective than that of dicloran(EC₅₀=15.89?g/mL),It provided a theoretical of a new antimicrobial.The innovation of this paper was combinated maleimides with three kinds of pesticide intermediate and anhydride,respectively the long carbon chain anhydride,which we hoped to get a new antimicrobial compounds.