Design，synthesis And Study About Relationship Between Structure And Communication Of2-Chloromethyl-1H-Benzimidazole And Its Derivatives

In the domestic and foreign pesticide research, the compounds of nitrogen heterocyclicbecome the main body of research, which result from its good selectivity, high activity,consumption and low toxicity and specificity in injurant biochemical physiological reaction.Additionally, because of it’s environmental friendly and characteristics of various structure.Compounds of nitrogen heterocyclic, especialy the kinds of benzimidazole have become thefocus of study.Benzimidazole, which is a core substructure and some important biological activitieswere resulted in various compounds. Similarly,2-substituted benzimidazole and theirderivatives have been found to be potent biological activities compounds as well.In this thesis, therefore, according princeple of the active structural stitching, wesynthesis a series derivatives by using parent nucleus of2-Chloromethyl-1H-benzimidazolereacted with various phenols. Additionally, we investigated their antifungal activities on5phytopathogenic fungi in vitro, and the structure antifungal activity relationships （SAR） ofcompounds were also discussed. The results were summarized as follows:1. In thesis, we use chloroacetic acid and the o-phenylenediamines as reactants tosynthesis2-Chloromethyl-1H-benzimidazoles, And through the reactions of acylation andetherification,35derivatives was synthesized. out of the35synthesized derivatives,22compounds （3,4a-d,4n,4o,5c, and7a-n） were new and reported for the first time. whichwas verified by web scifinder. The structures of the synthetic compounds were confirmed by1H NMR,¹³C NMR and MS, as well as HR-MS（ESI） spectral data and compound3wascharacterized by X-ray single crystal analysis.2. The Preliminary activities of the title compounds against5phytopathogenic fungiwhich are Alternaria solani, Botrytis cinerea, Colletotrichum gloeosporioides, Cytospora sp., Fusarium solani, were evaluated by mycelial growth inhibitory rate method at concentrationsof100μg/mL in vitro. In order to further confirm the activities performance of compounds,the IC50（median inhibitory concentration） values of compounds which inhibition rates over65%were determined. Compared with IC50values of the control hymexazol, the resultsindicated compounds6,4f,4m, and7f showed remarkable antifungal activities to one ormore of5phytopathogenic fungi. And, they have potential values for further study.3. Structure activity relationship （SAR） of these compounds was preliminarily studiedand discussed in thesis. The results revealed that the presence of the NO2group at the5-position of benzimidazole ring in6could be critical for antifungal activity. And results alsotold us chlorine atom plays an important role in the fungicidal activity of these compouds andso on. These discoveries provid some new basis for Structural modifications of fungicidalcompounds...