Synthesis And Antifungal Activities Of 7-aminocoumarin Nitrogen-containing Derivatives

Coumarin compounds are widely found in various natural plants,and it has many physical,chemical and biological activities,such as fluorescence,anti-virus,anti-fungal,antibacterial and parasites,anti-cancer.It had been received great attentions in medicine,agriculture,materials and other fields.Therefore,coumarin compounds in the field of new pesticides for fungicides,herbicides,pesticides and other aspects will have a broad prospects,causing widespread interest in the scientific community.Due to overused of pesticides for a long time,the existing pesticides are facing drug resistance and other issues.Fungi,bacteria and viruses caused by the disease has a short breeding cycle,the spread of fast and so on,but also the urgent need to constantly replace the pesticide to ensure adequate drug activity.Therefore,the development of pesticide varieties with novel skeleton structure and novel mechanism to meet the demand of agricultural production is the key to solve the grain problem.Because of that natural products has rich variety and biological activity,unique mechanism of action for people to develop new pesticides,one of the important sources of ideas.In this paper,we spliced coumarin fungicides and traditional nitrogen-containing heterocyclic fungicides and carbamates and other reactive groups to prepare a new pesticide-based pesticide compounds.Most of traditional coumarin compounds contains 7-hydroxyl groups and their derivatives,which synthesized from resorcinol.In this paper,in order to add amino groups at the 7th position of coumarin,we use 3-aminophenol as raw material and ethyl chloroformate protects the amino group.25 kinds of 7-carbamate coumarin are obtained by condensation of the Pechmann reaction with the β-keto acid under acidic conditions and the protecting group is removed under acidic conditions for 8 kinds of 7-amino coumarin core structure.Then the addition of pyrrole ring and pyrazole ring were introduced at the 7th position of coumarin.All the target compounds were characterized by 1H-NMR,13C-NMR,HRMS,IR.In this paper,six kinds of common fungi(Botrytis cinrea,Alternaria solani,Gibberella zeae,Rhizoctonia solani,Cucumber anthrax,Alternaria Leaf Spot)were tested by growth rate method.The results showed that most of the target compounds were used to study the effects of most of the target compounds on the growth of six kinds of fungi,(4a,4d,4h)and some 7-pyrrole coumarin(5g)were inhibited at the concentration of 100 μg/mL of the tested fungi up to 60%or more,4h on Rhizoctonia solani inhibition rate of 90%,the initial performance of a good bactericidal activity.We measured the EC50 toxicity of the compound with the antibacterial rate of more than 60%.It was found that the EC50 value of the compound 5g reached 4.47,which was further studied.