Studies On Synthesis And Herbicidal Activity Of Dioxoquinoxaline Ethanone Alkoxy Phosphorohydrazones And Substituted Sulfamides

Hydrazone compounds have good herbicidal, fungicidal, insecticidal and other biological activities and become one of research focuses of pesticides. Compounds of quinoxaline di-N-oxides is a class of substances with wide range of biological activity. Modifed such compounds’structure have some practical significance. Nowadays amino acid herbicides play an important role in the world herbicide market. As herbicide-resistant transgenic crops continue to expand rapidly, it is estimated that herbicides with such structures will also continue to develop. In order to find lead compound with novel structure and good biological activity, we designed and synthesized two series including 1,4-dioxide-3-methylquinoxaline-2-ethanone phosphorohydrazone and N, N’-di(carboxylate) substituted sulfonamide on the basis of the principle of combination of active structural moieties. Totally,17 target compounds of which 15 compounds have not been reported were obtained. Their structures were characterized by IR and 1HNMR. The general formulas of two series of compounds are list as follows:In this paper, different reaction conditions and their properties of physical, chemical and spectroscopy of these title compounds were systematically investigated.Using foliar spray application test, we select echinochloa beauvis and Oryza sativa as the representative of the monocotyledon and amaranthus ascendens loisel as the representative of the dicotyledon to test the two new series compounds’herbicidal activity.The result shows that, the herbicidal activity varies from different species tested and concentration of novel compounds. The two series of target compounds showed different degrees of inhibition on the echinochloa beauvis.1,4-dioxide-3-methyl-quinoxaline-2-ethanone dipentoxy phosphorohydrazone’s inhibition rate reach to 80% when the mass concentration of the compound is 800mg/L. N,N’-Bis(ethoxycarbonylmethyl)sulfamide’s inhibition rate reach to 62.00% when the mass concentration of the compound is 200 mg/L.1,4-dioxide-3-meth-ylquinoxaline-2-ethanone phosphorohydrazone compounds generally have weak activity in promoting growth on Oryza sativa. While only N,N’-Bis(a-ethyl acetate)sulfamide and N,N’-Bis(y-methyl-α-ethyl pentanoate)sulfamide have weak activity of inhibition on dicotyledon Canola when the mass concentration of the compound are 800 mg/L, which inhibition rate are 26.00% and 20.00% respectively. Overall, the new compounds’inhibitory activity on monocotyledon Echinochloa Beauvois are better than them on dicotyledon Canola. In addition, the structure-activity relationships of the target compounds were discussed.