Synthesis And Antibacterial Activity Of 2-Hydroxy-1-Naphthaldehyde-N(4)-Substituted Thiosemicarbazide And Their Mn(Ⅱ) And Co(Ⅱ) Complexes

2-hydroxy-1-naphthaldehyde Schiff base, thiosemicarbazide Schiff base and their metal complexes were showed a certain bacteria antibacterial activity, but they were not showed a certain fungi antibacterial activity. Therefore, in order to create synergies, improve the antibacterial activity and provide theoretical basis for the drug molecular design of fungi antibacterial activity, the author attempted to integrate antibacterial commonness of two kinds of Schiff base, a series of 2-hydroxy-1-naphthaldehyde-N(4)-substituted thiosemicarbazide and their Mn(II) and Co(II) complexes were synthesized. Their chemical structures were confirmed by FT-IR spectrum, 1H NMR spectrum, 13 C NMR spectrum, UV-vis spectrum and TG/DTA curves. The antibacterial activity and structure-activity relationship of Schiff base and their Mn(II) and Co(II) complexes to six crops fungal pathogens including rhizoctorzia solani, gibberella zeae, alternaria solani, fusarium wilt of cucumber, phytophythora infestans and phytophythora capsici were evaluated and speculated in vitro test.1. Ten kinds of N(4)-substituted thiosemicarbazide(1a~1j) were synthesized with aniline or some derivatives of aniline, carbon disulfide, hydrazine hydrate as the raw m-aterials and potassium hydroxide as the catalyst, including N(4)-phenyl thiosemicarbazide(1a), N(4)-o-methylphenyl thiosemicarbazide(1b), N(4)-m-methylphenyl thiosemicarbazi-de(1c), N(4)-p-methylphenyl thiosemicarbazide(1d), N(4)-o-methoxylphenyl thiosemicarb-azide(1e), N(4)-m-methoxylphenyl thiosemicarbazide(1f), N(4)-p-methoxylphenyl thiosemicarbazide(1g), N(4)-p-fluorophenyl thiosemicarbazide(1h), N(4)-p-chlorophenyl thiosem-icarbazide(1i) and N(4)-p-bromophenyl thiosemicarbazide(1j). Their chemical structures were confirmed by 1H NMR spectrum and FT-IR spectrum.2. Ten kinds of 2-hydroxy-1-naphthaldehyde-N(4)-substituted thiosemicarbazide(2a~2j) were synthesized with ten kinds of N(4)-substituted thiosemicarbazide and 2-hydrox-y-1-naphthaldehyde as the raw materials and hydrochloric acid as the catalyst, including 2-hydroxy-1-naphthaldehyde-N(4)-phenyl thiosemicarbazide(2a), 2-hydroxy-1-naphthaldehyde-N(4)-o-methylphenyl thiosemicarbazide(2b), 2-hydroxy-1-naphthaldehyde-N(4)-m-methylphenyl thiosemicarbazide(2c), 2-hydroxy-1-naphthaldehyde-N(4)-p-methylphenyl thi-osemicarbazide(2d), 2-hydroxy-1-naphthaldehyde-N(4)-o-methoxylphenyl thiosemicarbazide(2e), 2-hydroxy-1-naphthaldehyde-N(4)-m-methoxylphenyl thiosemicarbazide(2f), 2-hydr-oxy-1-naphthaldehyde-N(4)-p-methoxylphenyl thiosemicarbazide(2g), 2-hydroxy-1-naphth-aldehyde-N(4)-p-fluorophenyl thiosemicarbazide(2h), 2-hydroxy-1-naphthaldehyde-N(4)-chlorophenyl thiosemicarbazide(2i) and 2-hydroxy-1-naphthaldehyde-N(4)-p-bromophenyl t-hiosemicarbazide(2j). Their chemical structures were confirmed by 1H NMR spectrum,13 C NMR spectrum, UV-vis spectrum and FT-IR spectrum.3. Ten kinds of 2-hydroxy-1-naphthaldehyde-N(4)-substituted thiosemicarbazide Mn(II) complexes[2aMn(II)~2jMn(II)] and ten kinds of Co(II) complexes[2aCo(II)~2jCo(II)] were synthesized with 2-hydroxy-1-naphthaldehyde-N(4)-substituted thiosemicarbazide and Manganese(II) Acetate Tetrahydrate or Cobalt(II) Acetate Tetrahydrate. Their chemical structures were presumed by TG/DTA curves, UV-vis spectrum and FT-IR spectrum.4. It was found that Schiff base and their Mn(II) and Co(II) complexes were showed a certain antibacterial activity and related to the type and location of substituted of benzene of N(4)-substituted to six crops fungal pathogens in vitro test. The antibacterial activity of benzene of N(4)-substituted of compounds substituted had better than theirs not substituted. When benzene of N(4)-substituted of compounds substituted by electron-withdrawing groups, the higher the group electronegativity, the better antibacterial activity to gibberella zeae became. When benzene of N(4)-substituted of the target compounds para substituted by electron-donating group, these compounds had broad-spectrum antibacterial activity. The antibacterial activity of Mn(II) and Co(II) complexes had better than those Schiff base.