Studies On Synthesis And Bactericidal Activities Of Halogenated Polyphenyl Ethers

Halogenated hydroxy-diphenyl ethers are widely used as bactericide and germicide. They are applied in many fields, such as medicinal intermediates, agricultural pesticides, dyes, etc. It is valuable to study the new synthesis methods of halogenated hydroxy-diphenyl ethers and derivatives. In this dissertation a series of important results were obtained.The hydroxy-diphenyl ethers were synthesized through three steps reaction. First substituted nitro-diphenyl ethers were synthesized by the reaction of chloro-phenol, dichloro-phenol with chloro-nitrobenzene. Then the substituted amino-diphenyl ethers were obtained by reduction of substituted nitro-diphenyl ethers using iron and hydrochloric acid. Last halogenated hydroxy-diphenyl ethers were synthesized by diazotization and h'ydrolyzing of amino-diphenyl ethers. In this dissertation we study a new solvent free method to synthesize substituted nitro-diphenyl ethers. We have ameliorated the process of hydrolyzing of diazonium salt by improving of acid degree of the reaction system.For further studying the relationship of microorganism resistance and the chemical structure, we synthesized of a series of diphenyl ethers compounds which have different substituent and tested their bactericidal capability. Through this way we can find the relationship between the chemical structure and bactericidal capability. By simulation the structure of nature bacteriostat, we designed and synthesized of eight halogenated hydroxy-diphenyl ethers compounds based on the starting material hydroxy-diphenyl ethers and bromine. All of these halogenated hydroxyl-diphenyl ethers compounds have both chlorine and bromine as theirsubstituents. We test their bactericidal capability and find that these compounds have good antimicrobial on the grampositive-bacteria and gramnegative-bacteria.For studying the new derivatives of the hydroxy polyphenyl ethers, we design the triphenyl compounds. The halogenated triphenyl ethers are potential bactericide and insecticide. The third part of this article described the preparation of six halogenated nitro-triphenyl compounds with new structures by the reaction of hydroxy-diphenyl ethers with chloro-nitrobenzene. Six halogenated amido-triphenyl compounds were synthesized with new structures by reduction of substituted nitro triphenyl ethers using iron and hydrochloric acid We test their bactericidal capability and find that these two kinds of new derivatives have no bactericidal capability. In this part of our dissertation four halogenated hydroxyl triphenyl ethers were synthesized too and bactericidal capability testing show that this kind of new derivatives have good ability of microorganism resistance. From the study we can see the hydroxy is a important substituent in the structure of the polyphenyl ethers bacteria inhibitor.Thirty compounds were reported in this dissertation, twenty-three of them are reported for the first time. The chemical structure of these compounds have been confirmed by means of H1 NMR, MS, IR spectrum and elemental analyses.