Design,synthesis And Activity Evaluation Of Chrysanthemum Amide Compounds

Pyrethroids are one kind of effective pestcides which is very important for agricultural production.Cyclopropyl three-membered ring structure has long been regarded as the pesticide insecticidal activitycenter. In recent years, insect resistance is more and more serious because of the strain of heavy use ofPyrethroids pesticides. Currently many scientists use Pyrethroids as a lead compound in order to designand synthesize higher insecticidal activities pesticides.Chlorantraniliprole synthesized by Dupont has been widely used all over the world.They possessunique mechanism of action, wide insecticidal spectrum, low toxicity and environmental friendly.Scientists use chlorantraniliprole as a lead compound to do more deeply research and synthesize tens ofthousands of compounds. None of the compounds can exceed its insecticidal activity.With the method of substructure combination, forty-five novel chrysanthemum amide derivativeswere designed and synthesized from the aniline portion of chlorantraniliprole and the chrysanthemicacids of pyrethroids. The structures were characterized by 1H NMR, IR and ESI-HR-MS.Preliminary indoor biological activity determination indicate,all target compounds had certaininsecticidal activities against Plutella xylostella at the concentration of 500 mg/L and had60%-95%insecticidal activities against Myzus persicae and Tetranychus cinnabarinus in 48 hours.Target compounds including trifluoromethyl n24 has high activity, biological activity can reach 95%.Target compounds displayed 21%-70% fungicial activity on Rhizoctonia solani and other Four kinds offungi at the concentration of 200 mg/L. the target compounds including chrysanthemic acids withbenzene ring structure performed the best fungicial activity.Compounds with Iodine showed betterfungicial activity than compounds with Chlorine and Bromine. All the target compounds had certainbiological activity for weed.An effective and practical synthetic route was designed to accomplish the synthesis of novelchrysanthemum amide derivatives.2-aminobenzoic acid was employed as the starting raw material,which was underwent halogenation, cyclization with triphosgene,ring opening by methylamine and lastacylated with chrysanthemic acids.With the method of substructure combination, a series of newchrysanthemum amide compounds with good biological activity was synthesized by combining twoinsecticidal activity pieces together.But target compounds had insecticidal and fungicial activity, at thesame time had a certain herbicidal activity. This kind of compound mechanism remained to be furtherresearch.