The Synthesis And Activity Of 7-Aromatic Vinyl Coumarin Derivatives

Coumarin is an important class of heterocyclic aromatic oxygen compounds.It has a wide range of potential applications in the fields of food,medicine,pesticide etc.Researches on coumarin compounds has been very active.In this study,was designed and synthesized derivatives of coumarin-7-ene group and tested for biological activity of the target compounds.The main contents are as follows:1.Choice of o-methyl hydroquinone and ethyl acetoacetate as starting materials,that is cheap and easy to get.6-hydroxy-4,7-dimethyl-coumarin was synthesized by Pechmann method,and as a parent nucleus.The 6-hydroxyl modified into 6-methoxymethoxy,then the methyl of 7-position was bromide with NBS,last preparation wittig reagent with PPh3,and reacted with substituted benzaldehyde to synthesis of 17 7-aryl vinyl coumarin compounds through wittig reaction.2.The antifungicidal activities of 17 synthetic 7-aromatic vinyl coumarins against Botryodiplodia theobromae,Bipolaris cactivora,Lasiodiplodia theobromae,Botryosphaeria berengriana,Collectotrichum gloeosporioides and Colletotrichum musae were evaluated by the mycelium growth rate method.Experimental results show:(1)Seventeen 7-aromatic vinyl coumarin compound show varying degrees of inhibitory activity to six kinds of strains in the concentration of 100 μg/mL.Test results show that in respect of a whole series of compounds have poor inhibitory activity on Botryodiplodia theobromae,Bipolaris cactivora and Lasiodiplodia theobromae,but have a significant antibacterial activity on Botryosphaeria berengriana,Collectotrichum gloeosporioides and Colletotrichum musae.(2)On the basis of the preliminary antibacterial activity,evaluated the ECso of the compounds which inhibition rate reached more than 70%.Experimental results show that Compound Ia,Ie and Ik have significant inhibitory activity to Colletotrichum musae,their EC50 were 3.67 μg/mL,3.67 μg/mL and 0.42 μg/mL.3.Insecticidal activity test results show that the compound Ig,Ip and Iq have insecticidal activity against Pieris rapae crucivora and Aphidoidea,which corrected mortality was reached 60%after processing 24h,in the concentration of 100 μg/mL.4.Structure-activity relationship analysis of compounds found that,compounds would have a good inhibitory activity against to Botryosphaeria berengriana,C.ollectotrichum gloeosporioides and Colletotrichum musae when R substituent was methoxy or halogen substituent.F and Cl of halogen group substituent have a better antifungicidal activity,and the R substituent group on opposite position have the best activity.The compounds which R substituent was F or CF3 group having insecticidal activity.