Russian Journal of General Chemistry最新文献

In this study, a series of novel 1,3,4-oxadiazole thioether derivatives incorporating a methylsulfonyl moiety were synthesized and their structures were characterized by ¹H, ¹³C NMR, and HRMS. Bioassay results demonstrated that the target compounds exhibited moderate to good in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas axonopodis pv. citri (Xac), and Wickerhamomyces anomalus (Wa). Notably, 2-[(4-fluorobenzyl)thio]-5-[4-(methylsulfonyl)phenyl]-1,3,4-oxadiazole showed excellent antibacterial activities against these pathogens at concentrations of 200 and 100 μg/mL, with inhibition rates of 90 and 76% for Xoo, 84 and 64% for Xac, and 96 and 81% for Wa, respectively, which were even better than thiodiazole copper. However, the target compounds exhibited certain in vitro antifungal activities against Penicillium sumatraense (Ps) and Aspergillus fumigatus (Af) at 50 μg/mL, with the inhibition rates of 25–46 and 18–42%, respectively, which were lower than those of prochloraz. To the best of our knowledge, it is the first report on the synthesis and bioactivity evaluation of this series of 1,3,4-oxadiazole thioether derivatives incorporating a methylsulfonyl moiety.

Herein, a series of novel sulfone derivatives incorporating an 1,2,4-triazole moiety was synthesized and their structures were confirmed by ¹H NMR, ¹³C NMR, and HRMS. The in vitro antibacterial activities of these compounds against Wickerhamomyces anomalus (Wa) and Bacillus cereus (Bc) at concentrations of 200 and 100 μg/mL were evaluated using the turbidimeter tests. The results demonstrated that the target compounds exhibited moderate to good antibacterial activities against Wa and Bc. Notably, 3-{[(4-chlorophenyl)sulfonyl]methyl}-5-[(4-fluorobenzyl)thio]-4-methyl-4H-1,2,4-triazole showed excellent in vitro antibacterial activity against Bc at 200 μg/mL, with a 100% inhibition rate. Additionally, the in vitro antifungal activities of these compounds against Penicillium sumatraense (Ps) and Aspergillus fumigatus (Af) were assessed using the mycelium growth rate method. Bioassay results indicated that the target compounds exhibited certain antifungal activities against Ps and Af at 50 μg/mL. Specifically, 3-{[(4-chlorophenyl)sulfonyl]methyl}-4-phenyl-5-(propylthio)-4H-1,2,4-triazole displayed moderate antifungal activity against Ps at 50 μg/mL, with an inhibition rate of 64.52%. To the best of our knowledge, this study is the first to report on the synthesis and bioactivity evaluation of this series of novel sulfone derivatives incorporating an 1,2,4-triazole moiety.

Discovering super-efficient herbicides with novel structures is one of the effective ways to solve the increasingly severe weed resistance problem and meet ecological requirements. In this work, a series of novel bromo-p-hydroxybenzamides were designed based on the molecular hybridization strategy, and rapidly synthesized by one-step amidation reaction, and then characterized by ¹H NMR, ¹³C NMR and HRMS. The herbicidal activity assay indicated that most of the target compounds exhibited good-to-excellent inhibition effects on seed germination of two model plants. At a concentration of 100 mg/L, the inhibition rate of 3,5-dibromo-N-(4-bromo-3-chlorophenyl)-p-hydroxybenzamide reached up to 98 and 96% on the roots and stalks of the monocotyledonous barnyard grass (E. crus-galli), respectively. 3,5-Dibromo-N-(2-bromophenyl)-p-hydroxybenzamide showed excellent inhibitory activity on the roots and stalks of dicotyledonous rape (B. napus) at 100 mg/L, with an inhibitory rate of more than 90%. Furthermore, the concentration was reduced to 1 mg/L, the inhibitory rate of 3,5-dibromo-N-(2-bromophenyl)-p-hydroxybenzamide on the roots of B. napus was still as high as 90%. This work provides a novel molecular scaffold for the development and research of new super-efficient herbicides.

Abandoned biomass derived from agricultural production has been widely applied to deal with environmental challenges. This work prepared biochar modified by zinc and manganese (Zn/Mn–BC) through straightforward impregnation pyrolysis for the removal of oxytetracycline from wastewater. Characterizations, adsorption performance, reusability, and mechanisms were studied. Results showed that the Zn/Mn–BC had the highest OTC adsorption capacity (60.81 mg/g) and exhibited finer separation performance at low OTC concentrations. Notably, Zn/Mn–BC can keep a high removal rate (75.86%) of OTC after 5 cycles. The kinetic and isotherm models reveal that the adsorption process is multi-layer chemisorption. Thermodynamic data indicates that OTC adsorption by Zn/Mn–BC is an exothermic, spontaneous process with decreasing entropy. In addition, the possible mechanisms of adsorption are mainly electrostatic, hydrogen bonds, π–π stacking interactions, and especially metal oxide bonds (M–O) for OTC removal. This study not only realizes the strategy of turning waste into a treasure of chestnut shell but also provides an alternative and sustainable adsorbent for antibiotics from wastewater.

This study focuses on the synthesis of novel organic compounds with potential antioxidant activity. The intermediate hydroxychalcone derivative was synthesized via Claisen-Schmidt condensation and then reacted with chloroacetamide derivatives to produce the target compounds. The biological activity of these compounds was evaluated in vitro by DPPH assay and theoretically using molecular docking. The results obtained support the tested compounds’ importance in free radical scavenging which showed promising inhibitory potential against free radical. The high inhibition percentages of these compounds (up to 88.8% at a concentration of 500 μM) compared to ascorbic acid may be due to their structural properties attracting to the free radicals.

Based on 3-chloro-6-hydrazinylpyridazine, a series of new derivatives containing the arylidenehydrazinyl-6-chloropyridazine fragment, were synthesized using conventional methods and under microwave irradiation. Experimental data indicate that when using a technique that meets the requirements of green chemistry, in the vast majority of cases higher yields of final products are achieved with a simultaneous sharp reduction in reaction times, which leads to significant savings in energy resources. Biological tests were carried out on seeds and seedlings of common bean (Phaseolus vulgaris L.). The screening showed that the synthesized compounds exhibit pronounced stimulating activity in plant growth and may be promising in searching for new growth stimulators. In silico study of synthesized compounds were carried out.

The reactions of nickel(II) with (S)-[(prop-2-en-1-yl)oxy]ethanimidothioate (PENT) and (S)-[(prop-2-yn-1-yl)oxy]ethanimidothioate (PINT) was studied by the extraction-photometric method. The ligands were characterized with IR and NMR spectroscopy. The influence of aqueous phase pH on the formation of Ni(II)L₂ complexes and thermal decomposition were studied. The developed extraction-photometric method was applied to determine nickel in wastewater and plant samples.

The composition of solvate complexes of LiClO₄, LiSO₃CF₃, LiN(SO₂CF₃)₂, LiBF₄, and LiPF₆ with sulfolane formed from lithium salt solutions at 40, 50, 60, and 70°C has been studied by vacuum gravimetry method. It has been shown that the composition of the solvate complexes is determined by the temperature of their formation and the nature of the lithium salt anion. The specific ion conductivity of the solvate complexes has been in the range of 0.4–1.8×10^–3 S/cm, and the cationic conductivity has been in the range of 0.3–0.8×10^–3 S/cm. The sulfolane-based solvate complexes have exhibited high thermal stability (>320°C) and have existed in the liquid state over a wide temperature range.

The reaction of vanillin (Van) with baclofen (Bac) was studied kinetically in an aqueous acidic medium. The reaction product was examined using ¹H, ¹³C NMR and IR spectroscopy methods, in addition to ultra-performance liquid chromatography (UPLC). Moreover, the reaction was monitored spectrophotometrically, with (0.1–0.4) × 10^–4 mol/dm³ of Bac, (0.5–5.0) × 10^–2 mol/dm³ Van and 0.2–1.0 mol/dm³ ionic strength (I) over the temperature range of 40–60°C. The reaction is first order with respect to [Van] and [Bac], and the rate of the reaction decreases as pH increases in the range of 3.60–4.66. In addition, the effect of catalyst on the rate of the reaction was studied, and the thermodynamics activation parameters involving ∆H^* and ∆S^* were calculated. The rate of the reaction obeys the rate law d[Bac–Van]/dt = {k₂ + (k₄ + k₃[H⁺])[Van]} × [Bac]. This experimental rate law is consistent with a mechanism in which both the protonated and unprotonated forms of Van are involved in the rate-determining step, with the protonated species being the more reactive form. Furthermore, density functional theory (DFT) was performed to search the geometries of the final product resulting from the reaction between Bac and Van. Finally, interaction region indicator (IRI) calculations were used to reveal chemical bonding and weak interaction in the coupled compound Bac–Van.

The mechanism of the cycloaddition reaction between singlet Me₂Ge=Ge: and formaldehyde has been investigated with the MP2/6-311++G** method in this article, it could be predicted that the reaction has one dominant reaction pathway. The dominant reaction pathway consists of three elementary reactions: (1) the two reactants form a four-membered Ge-heterocyclic ring germylene; (2) the four-membered Ge-heterocyclic ring germylene further reacts with formaldehyde to form an intermediate; (3) the intermediate isomerizes to a spiro-Ge-heterocyclic ring compound via a transition state.