Synthesis And Biological Activity Of Novel Cyanoacrylate Compounds Containing Heterocycles

Cyanoacrylates are a kind of important PSII electron transport inhibitors,which can prevent the combination of D1 protein in PSII and QB and destroy the photosynthesis of weed. Relevant research shows that the nature of substituent groups on cyanoacrylates can cause a huge change in the biological activities. Cyanoacrylates not only show high herbicidal activity but also have good antitumor activity. Hence it has become one of the hot spots in the field of new pesticides.Heterocyclic compounds are an important part of the biologically active compounds and 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 find highly active cyanoacrylate compounds, we used Z-ethoxyethyl-2-cyano-3-methylthio-3-(2-chloro-5-pyridyl)methanaminoacrylate as a leading compound to design and synthesize four series of novel cyanoacrylates with pyrimidine, oxadiazole, pyrazole and coumarin heterocyclic moieties. We also explored and optimized the synthesis methods of some intermediates and target compounds. The structures of all the target compounds were confirmed by 1H NMR, 13 C NMR and elemental analysis, some of the target compounds were analyzed by mass spectrometry. Some of these compounds were assayed for herbicidal activity and other biological activities.The results exhibited that pyrimidine containing cyanoacrylates have moderate herbicidal activities,and some of the pyrimidine derivatives showed better herbicidal activities than the reference sample NK-9717.Besides,some cyanoacrylates bearing pyrazole showed favorable antitumor activity,but they have no good herbicidal activities, some cyanoacrylates containing oxadiazole and coumarin show low herbicidal activities.