The Research Of New Cyanoacrylates With Nitrogen-containing Heterocyclic Compounds

Cyanoacrylates have been the subject of intense interest for the past decades as one kind of herbicides. A detailed study of these compounds revealed that cyanoacrylates are inhibitors of photosystem II(PS II) electron transportation, which inhibits the growth of weeds by disrupting photosynthetic electron transportation at a common binding domain on the Dl protein (32kDa polypeptide) of the PS II reaction center. In recent years many cyanoacrylates containing heterocycles exhibited excellent herbicidal activities, insecticidal activities, fungicidal activities, anticancer activities or antivirus activities. Therefore, the research in this field have good prospects for development.Heterocyclic compounds especially nitrogen-containing heterocyclic compounds are an important part of the biologically active compounds and are widely used in the field of medicines and pesticides, for example, the active ingredients in herbal alkaloids or some vitamins and antibiotics are mostly heterocyclic compounds. Heme, chlorophyll and nucleic acid which play an important physiological role of bases in animals and plants are nitrogen-containing heterocyclic compounds also. In recent years, due to the awareness of pesticide safety requirements, many of the traditional pesticides such as organophosphate pesticides and organochlorine pesticides gradually withdraw from the stage of pesticide, while the nitrogen-containing heterocyclic pesticides have been a hot area of pesticide and opened a new era of green pesticide research due to its advantage of high activity, high selectivity, low toxicity, and environment-friendly.In order to further study the structure-activity relationship of different substituents in cyanoacrylates and look for new herbicides with improved prifiles, we used (Z)-ethoxyethyl-2-cyano-3-methylthio-3-(2-chloro-5-pyridyl)methanaminoacrylate as a leading compound to design and synthesize 14 series of novel cyanoacrylates with nitrogen-containing heterocyclic compounds using bioisoterism and union of active group. 120 Novel target compounds and 17 novel intermediates were synthesied. The structures of the compounds were confirmed by NMR, IR, MS, elemental analysis(or HRMS analysis) and X-ray diffraction. The bioactivity tests showed that most of the compounds showed good herbicidal activities and excellent selectivity, some of the compounds also have fungicidal activities and plant growth regulatory activities. We have laid a solid theoretical and experimental basis on the research of cyanoacrylates in the future.