The Design Synthesis And Pesticidal Activities Of6-Esterified Coumarins And6-Etherified Coumarins

Coumarin is a class of compounds with benzopyrone mother nuclear structure in General. It has two sources, one is extracted directly from plants, the other is a biomimetic synthesis. Coumarin and coumarin derivatives of species are very few if extracted directly from plants, most researchers focus on the release of coumarin and coumarin derivatives synthesis. Coumarin derivatives are used in the field of medicine, dyes, spices and agricultural, it has really high research value. This article consists of following two elements.1. I synthesized6-hydroxy-4,7-dimethyl coumarin and3-chloro-6-hydroxy,7-dimethyl coumarin according to Pechmann's Law, and used them as raw material, modified its hydroxyl, and further combines the coumarin derivative containing an ester group, an ether group. Using aryl benzoyl chloride as raw material, through esterification modification of the hydroxyl of coumarin.45kinds of ester containing coumarin derivatives were synthesized. Using substituted benzyl chloride as the raw material, through etherification modification of hydroxyl coumarin hydroxy, got12kinds of coumarin derivatives containing ether.2. After studied agricultural activity of those57kinds synthesized coumarin derivatives, the results are as follows:(1) Use Aphis gossypii, Aphis craccivora, Tetranychus cinnabarinus, Orgyia postica, Culex pipiens pollens as tested insects, studied the insecticidal activity. Results showed that, compounds3m,3u,3x,3ff and3gg show over90%insecticidal activities against Aphis gossypii; compounds3h and3aa show over90%insecticidal activities against Aphis craccivora; compounds3ff,3ii,3ll and3nn show over90%insecticidal activities against Tetranychus cinnabarinus; compounds3t and3bb show over90%insecticidal activities against Orgyia postica; and the3gg show over80%insecticidal activities against Aphis gossypii and Aphis craccivora, show high insecticidal activities.(2) Use pathogenic fungus of Colletotrichum musae, Fusarium oxysporum, Botryodiplodia theobromae, Colletotrichum gloeosporioiles, Colletotrichum gloeosporioides, Corynespora cassiicola, Pestalotia palmarum, to study the fungicidal activity. Results showed that, compound3q show71.53%fungicidal activity against Colletotrichum musae, show74.69%fungicidal activity against Botryodiplodia theobromae, show74.69%fungicidal activity against Colletotrichum gloeosporioilesm; compound4b show91.58%fungicidal activity against Botryodiplodia theobromae; compound4c show90.59%fungicidal activity against Botryodiplodia theobromae; compound4e show91.49%fungicidal activity against Botryodiplodia theobromae; compound41show74.93%fungicidal activity against Collelotrichum gloeosporioides; the performance of a certain fungicidal activity.(3) Use Crotalaria, Mimosa, Bidens pilosa, Echinochloa crusgalli, radish, cucumber as tested plants, to study the herbicidal activity. Results showed that, the activity of more than80%of the6active compounds,3o,3z,3oo and3qq show83.67%herbicidal activity against Mimosa; compound3m show80.50%herbicidal activities against Crotalaria; compound3a show83%herbicidal activity against Bidens pilosa; and besides above we have28kinds of compounds have a high fungicidal activities in70%to80%.(4) Combined with the structure and activity of those compounds, we found that, compounds with high activity also had benzene in C6-substituent, the halogen substituted in benzene had higher activity than others, and the chlorine substituted got the best activity, we can them for further optimization.