Synthesis And Fungicidal Activity Of Benzoyloxyacetamino/ Imidazolidinones Based On Pyridine Moiety

Pyridine is an isoelectric of benzene,but its electron cloud density and hydrophobic constant is lower than benzene,which has become the focus of new drug research.Facts have proved that pyridine derivatives tend to have higher biological activity,high internal absorption,and high selectivity.Therefore,pyridine derivatives are widely used in the field of pesticides.In addition,amide compounds have been developed as herbicides,bactericides,and insecticides for more than 50 years.Due to their high activity and long-acting time,they have always been the focus of pesticide research and development.Imidazolinone derivatives are also a class of heterocyclic compounds with good biological activity and pharmacological activity.They also have been used as herbicides and fungicides for many years.In order to find novel lead compounds of pyridine structure with high activity,two synthetic routes have been designed according to related literature reviews.The research contents and results of this paper are as follows:1.We selected the bisocyanurin derivatives 2-(4-chlorophenyl)-2-propionyloxyacetamide with good bactericidal activity as the lead,the 3-picolyl group of pyridoxime was introduced into the lead using the method of active substructures combination.At the same time,in order to increase the antibacterial activity,tbutyl groups or 1,1,3,3-tetramethylbutyl groups with larger molecular volume was introduced to replace the two phenylethyl substituted groups to improve the affinity of drug molecules with plant pathogens.So we designed a series of N-tert-butyl-2-(pyridin-3-yl)2-(substituted benzoyloxy)acetamide and N-(1,1,3,3-tetramethyl-butyl)-2-(pyridin-3-yl)-2-(substituted benzoyloxy))acetamide(shown as the series I and series II).2.We introduced the pyridylmethylamino group into the active structure of benzylideneimidazolidone using the principle of active substructure splicing.We synthesized a series of imidazolinone derivatives without pyridine structure,which has never been reported by literatures(shown as series III).3.The antifungal activities of 34 target compounds were tested by means of mycelium growth rate method.The results showed that the compounds I_a,I_k,II_a,II_d,II_g,II_i,II_j,and IIk exhibited moderate inhibitory activity against S.sclerotiorum at 50?g/m L,the inhibition rate was 78%to 87%;near to or higher than the control agents chlorothalonil and triadimefon.The target compounds I_k,II_a,II_k,III_d and III_h had high inhibitory activity against B.cinerea and the antibacterial activity high lights up to 100%at 100?g/mL.However,all compounds exhibit morderate inhibitory activity against B.cinerea.