Synthesis And Biological Activity Of Pyrimidine Guanidine Compounds

Pyrimidine derivatives are heterocyclic compounds with a wide range of biological activities.They have bactericidal,insecticidal,herbicidal,antiviral,and anti-inflammatory functions.They are widely used in the fields of medicine and pesticides.The guanidine group in organic guanidine compounds can be fully protonated under physiological conditions and can react with groups or elements in the organism,thereby affecting the normal substance or energy metabolism of the organism.In order to create new pesticides with high efficiency,low toxicity and good environment,this paper designed and synthesized a series of novel pyrimidine guanidine compounds.A variety of bioassay methods were used to target tobacco mosaic virus,phytopathogenic fungi,phytopathogenic bacteria,and weeds as target organisms.The biological activities of the compounds were evaluated,and a preliminary structure-activity relationship analysis was performed.The conclusions are as follows:1.Using substituted acetophenone and ethyl fluoroacetate as starting materials,37 1,3-diketone intermediate compounds were synthesized by Claisen ester condensation reaction.The intermediate was dehydrated and condensed with morpholine hydrochloride to synthesize 37 new pyrimidine guanidine target compounds.The structures of all compounds were confirmed by ¹H-NMR,¹³C-NMR and MS.2.The target compound was tested for resistance to tobacco mosaic virus using the blob method.The test results showed that at a concentration of 0500 ?g / m L,most of the target compounds were more effective against tobacco mosaic virus.Good inhibitory activity,among which compounds GLY-15,GLY-22,GLY-23,GLY-32 have TMV inhibition rates of 80.29%,87.60%,82.55%,and 86.78%,which are significantly higher than those of the control agent morpholinoguanine hydrochloride?Inhibition rate was 76.12%?and Ningnanmycin?inhibition rate was 68.65%?.At aAbstract concentration of 400 ?g / m L,the compounds GLY-15 and GLY-37 still maintainedgood inhibitory effects?inhibition rates were 75.37% and 71.64%,respectively?,which were significantly higher than those of the control agent Ningnanmycin?inhibition rate was 52.88%?.And morpholinoguan hydrochloride?inhibition rate was49.52%?.The mycelial growth rate method and pot method were used to determine the fungicidal activity of the compounds.From the test results,this series of compounds has a broad spectrum of fungicidal activity.Highly active compounds GLY-13 and GLY-19 against Pyricularia grisea and Fusarium graminearum were selected.The compound GLY-18 with high activity against Sclerotinia sclerotiorum was screened.The high-throughput screening method was used to test the bactericidal activity of this series of compounds against four pathogenic bacteria,such as Erwinia carotovora,Clavibater michiganensis,Xanthomonas campestris pv.Citri Hasse Dye and Xanthomonas campestris pv.Vesicatoria..From the test results,this series of compounds has a broad spectrum For bacterial activity,GLY-30,GLY-32 and GLY-36 compounds with high activity against E.carotovora were screened out,and GLY-32 and GLY-36 compounds with high activity against X.campestris pv.Citri Hasse Dye were selected..Using the rhizome suppression method,Echinochloa crusgalli and Abutilon theophrasti were used as test objects,and the target compound was tested for herbicidal activity at a concentration of 100 ?g / m L.The results showed that the herbicidal activity of the compound on E.crusgalli was significantly higher than that of A.theophrasti.Therefore,this series of compounds need further structural optimization to improve herbicidal activity.Through the biological activity analysis of the synthetic pyrimidine guanidine compounds,the structure-activity relationship of the target compounds was summarized.In summary,pyrimidine guanidine compounds have higher application value and better application prospects,and provide a theoretical basis for further compound design and screening of target for activity determination.