Synthesis and pesticidal activity of new N-alkyl-N-[1-(2-hydroxyphenyl) ethyl]amines

A series of novel N-alkyl-N-[1-(2-hydroxyphenyl) ethyl]amines were synthesized as potential new agents to control pests. Their structures were confirmed on the basis of IR, NMR and elemental analyses. Six new N-alkyl-N-[1-(2-hydroxyphenyl) ethyl]amines were prepared by reduction of corresponding Schiff bases using sodium borohydride in 80–87 % yields. These compounds were tested for their antifungal activity against two pathogenic fungi viz., Rhizoctonia bataticola ITCC 0482 and Sclerotium rolfsii ITCC 5226 and for insecticidal activity against insects of stored grain pest Callosobruchus analis. Fungicidal bioassay revealed that compound N-Decyl-N-[1-(2-hydroxyphenyl)ethyl]amine, was highly effective against R. bataticola (ED₅₀ 6.86 mg L^?1) which was comparable with that of commercial fungicide hexaconazole (ED₅₀ 6.35 mg L^?1). Also compounds N-Heptyl-N-[1-(2-hydroxyphenyl)ethyl]amine, N-Octyl-N-[1-(2-hydroxyphenyl)ethyl]amine and N-Nonyl-N-[1-(2-hydroxyphenyl)ethyl]amine displayed promising fungitoxicity against same pathogen. However, compound N-Heptyl-N-[1-(2-hydroxyphenyl)ethyl]amine was also found to be effective against S. rolfsii (ED₅₀ 4.92 mg L^?1 as against 1.27 mg L^?1 for hexaconazole). Compound N-Hexyl-N-[1-(2-hydroxyphenyl)ethyl]amine was most effective as insecticide followed by compound N-Octyl-N-[1-(2-hydroxyphenyl)ethyl]amine. LC₅₀ values for these compounds were 155.0 and 275.0 mg L^?1 respectively as against 36.70 mg L^?1 for commercial insecticide dichlorovos. The results obtained from bioassays indicate that this class of compounds can be utilized for the design of new substances endowed with pesticidal activities.     

Synthesis,structural elucidation,electro-chemical behaviour and fungitoxic activity of transition metal(II) mixed-ligand complexes with some Schiff bases

The Schiff bases, potassium salt of salicylidene-β-alanine [KHL], bis(benzylidene)ethylenediamine [SB¹] and thiophene-o-carboxaldene-p-toluidine [SB²], and mixed-ligand complexes with Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) have been prepared. They were characterized by elemental analyses, magnetic susceptibility measurements, thermogravimetric analyses (t.g.a.), infrared spectra and electronic spectra. The mixed-ligand complexes were found to have the general composition [M(L)(SB)(H₂O)]. All the mixed-ligand complexes were found to have six-coordinated octahedral geometry. The fungitoxic activity of the ligands, metal salts, control (DMSO), bavistin, emcarb, and mixed-ligand complexes were screened against Aspergillus niger, Fusarium oxysporum and Aspergillus flavus. All the mixed-ligand complexes show higher fungitoxic activity as compared to the Schiff bases, metal nitrate and control (dimethyl sulphoxide, DMSO), and moderate fungitoxic activity as compared to the fungicides (bavistin and emcarb).     

Study on increase in toxicity of Schiff bases on microorganism on chelation with metal

New heterochelates of the type [M(L)(SB)(H₂O)] (where M?=?Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II), KHL?=?potassium salt of salicylideneglycine and SB?=?thiophene- O -carboxaldeneaniline) have been synthesized. The heterochelates have been characterized on the basis of elemental analyses, electronic spectra, and magnetic measurement analyses. The structural and geometrical conformation has been discussed on the basis of IR spectral data. A thermal study of the complexes has been carried out to ascertain their thermal stability. Magnetic susceptibility measurements and electronic spectral data suggest a six-coordinated octahedral structure for these complexes. The increase in toxicity of the investigated heterochelate metal compounds was tested against three gram-negative bacteria, S. typhi, E. coli, and Serratia marcescens by the disc diffusion method. It is observed that the heterochelates show higher toxicity when compared to the Schiff bases, metal salts, and control (DMSO) due to chelation. The toxicity is also compared to the standard drug tetracycline.     

Microwave synthesis,characterization, and bio-efficacy of novel halogenated Schiff bases

A new series of halogenated Schiff bases was synthesized by the condensation of 5-fluoro-2-hydroxy acetophenone and 3,5-dichloro-2-hydroxy acetophenone with different alkyl amines, namely propyl, pentyl, hexyl, heptyl, octyl, nonyl, dodecyl, tetradecyl, hexadecyl, and octadecyl amines, under microwave irradiation. Newly formed molecules were characterized by Infrared and nuclear magnetic resonance (¹H NMR and ¹³C NMR) spectroscopic techniques. Further, the Schiff bases were screened for antifungal bioassay, and the results showed potential fungicidal activity against two very important plant infecting fungi, viz. Rhizoctonia solani and Sclerotium rolfsii. Among the screened compounds, 2,4-dichloro-2-[1-(propylimino)ethyl]phenol was found to be the most active compound against both R. solani (ED₅₀ 8.02 mg L^?1) and S. rolfsii (ED₅₀ 21.51 mg L^?1) followed by 2,4-dichloro-2-[1-(pentylimino) ethyl]phenol (ED₅₀ 13.02 and 29.57 mg L^?1, respectively). The synthesized compounds were also screened for antioxidant activity by 2,2-diphenyl-1-picrylhydrazyl (DPPH)-free radical scavenging technique. All the compounds showed very low to moderate activity as compared with Gallic acid.     

One-step preparation of polyimide-inlaid amine-rich porous organic block copolymer for efficient removal of chlorophenols from aqueous solution

A novel polyimide-inlaid amine-rich porous organic block copolymer (PI-b-ARPOP) was prepared via one-step polymerization by using different molar ratios of melamine (MA)/terephthalaldehyde (TA)/pyromellitic dianhydride (PMDA), at molar ratios of 4/3/1, 4/2/2 and 4/1/3. The copolymer contained both aminal groups belonging to ARPOP and imide groups belonging to PI, and the bonding styles of the monomers and growth orientations of the polymeric chains were diversiform, forming an excellent porous structure. Notably, MA/TA/PMDA (4/2/2) had a surface area and pore volume of 487.27?m²/g and 1.169?cm³/g, respectively. The adsorption performance of the materials towards 2,4-dichlorophenol (2,4-DCP) in ultra-pure water was systematically studied. The pH value of 7 was optimal in aqueous solution. Na⁺ and Cl^? ions did not negatively affect the adsorption process, while humic acid (HA) slightly decreased the capacity. The equilibrium time was 40 sec, and the maximum adsorption capacity reached 282.49?mg/g at 298?K. The removal process was endothermic and spontaneous, and the copolymer could maintain its porous structure and consistent performance after regeneration by treatment with alkali. Moreover, to further assess the practical applicability of the material, the adsorption performance towards 2,4-DCP in river water was also investigated. This paper demonstrated that the PI-b-ARPOP can be an efficient and practical adsorbent to remove chlorophenols from aqueous solution.     

西夫(Schiff)碱侧链聚硅氧烷毛细管柱气相色谱固定相的制备与色谱性能

将合成的西夫 (Schiff)碱侧链聚硅氧烷高分子液晶化合物用作毛细管柱气相色谱固定相 ,具有较高的柱效 ,热稳定性较好 ,最高柱温可达 2 80℃ ,对苯的各种取代物、酚类及多环芳烃有良好的选择性 ,尤其对位置异构体有独特的分离效果。     

微波辐射合成酪氨酸席夫碱及其光度法测定蔬菜中钴的研究

在微波辐射下 ,合成酪氨酸与桑色素席夫碱 ,该方法有很多优点 .缩短反应时间 ,仅 1 0min完成反应 ,产率在 88.5 %～ 90 .1 % ,该席夫碱应用于光度法测定蔬菜中钴的含量 .实验表明 ,钴与酪氨酸席夫碱形成 1∶1络合物 ,最大吸收波长λmax =670nm ,摩尔吸光系数为 5 .2× 1 0 4L·mol- 1 ·cm- 1 ,方法对于测定蔬菜中的钴 ,结果较满意 .     

Spectroscopic studies and biological evaluation of some transition metal complexes of a novel Schiff base ligands derived from 5-arylazo-salicyladehyde and o-amino phenol

Synthesis and characterization of Cu(II), Ni(II), and Zn(II) Schiff bases complexes resulted from the condensation of salicylaldehyde derivatives with o-amino phenol were discussed using elemental analysis (carbon, hydrogen, and nitrogen), molar conductance, magnetic measurements, mass spectra, and electronic spectra. The essential bands of infrared, ¹HNMR, and UV-Vis spectra as well as thermogravimetric analysis corresponding to the active groups within the three ligands and their complexes were interpreted. The dehydration and decomposition processes of the [Cu(H₂L₁)(H₂O)](OAc)₂, [Ni(H₂L₁)(H₂O)]SO₄ · H₂O, [Zn(H₂L₁)(H₂O)]SO₄ · H₂O, [Cu(H₂L₂)(H₂O)](OAc)₂, [Ni(H₂L₂)(H₂O)]SO₄ · H₂O, [Zn(H₂L₂)(H₂O)]SO₄ · 2H₂O, [Cu(H₂L₃)(H₂O)](OAc)₂ · H₂O, [Ni(H₂L₃)(H₂O)]SO₄ · 2H₂O, [Zn(H₂L₃)(H₂O)]SO₄ complexes were studied thermodynamically using the integral method applying the Coats–Redfern and Horowitz–Metzger equations and the thermodynamic parameters were calculated. It was found from the elemental analysis and the thermal studies, that the ligand behaves as tridentate ligand forming chelates with 1 : 1 (metal : ligand) stoichiometrically. The molar conductance measurements of the complexes in dimethyl sulfoxide solvent indicate that the complexes have an electrolytic nature. The biological activities of the three ligands in comparison with metal(II) complexes were studied against different Gram positive and Gram negative bacteria.     

Synthesis and biological activities of new azacrown ether Schiff bases and spectrophotometric studies of their complexation with [60]fullerene

A series of novel azacrown ether Schiff bases 1–3 have been synthesized in good yield and in a simple way. Their host–guest interaction with [60]fullerene has been studied in toluene by absorption spectroscopic method. All the complexes are found to be stable with 1:1 stoichiometry. Because of their potential applications in industry, agriculture and medicine, they were investigated for their mutagenic and antimutagenic activities using the spot test and the plate incorporation assay of Ames. Compounds 1, 2 and 3 were found to be nonmutagenic in the Ames test using strains TA 1535, TA100 and TA97a of Salmonella typhimurium. However, using strain TA102 revealed that, although both compounds 1 and 2 were nonmutagenic, compound 2 gave a positive response indicating that it acts as an oxidative mutagen. The structure-activity relationship may throw some light on the biological activity of such series of compounds.     

Removal of Fe(III) using a polystyrene anchored Schiff base

Salicylaldehyde Schiff base of amino-methylated polystyrene has been developed as a novel reagent for the removal of Fe(III) from solutions. The selectivity of the metal ion uptake over a wide range of different concentrations of metal ion, effect of pH, ligand concentration and the influence of other foreign ions were studied. A very good selectivity was achieved for the removal of the ion. It was found that 0.01 g of the ligand was sufficient to achieve about 96% removal of the metal ion in terms of concentration (ppm) from a 30 ppm solution in acidic pH.