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Advances of Heterocyclic Chemistry with Antibacterial and Antifungal Activity
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Advances of Heterocyclic Chemistry with Antibacterial and Antifungal Activity

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 April 2024) | Viewed by 12582

Special Issue Editor

Dr. Pei Li

E-Mail Website
Guest Editor
Qiandongnan Engineering and Technology Research Center for Comprehensive Utilization of National Medicine, Kaili University, Kaili, China
Interests: pesticide synthesis; fungicide; natural product; organic synthesis; green pesticide
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Global food safety/security will remain a worldwide concern for the next 50 years and beyond. Plant bacterial and fungal diseases have had an enormous impact on food safety/security at various stages of the food chain, from primary production to consumption. Although pesticide application has been the conventional methodology used in plant protection, frequent use of conventional chemical pesticides has resulted in problems in resistance in bacteria and fungi populations, environmental contamination, and human health. Therefore, the current paradigm of relying almost exclusively on conventional chemical pesticides for plant bacterial and fungal disease control may need to be reconsidered. In the past decade, due to the good selectivity, high activity, low dosage, and low toxicity, heterocyclic compounds show an important role in the development of novel heterocyclic pesticides. So far, more than 50 heterocyclic pesticides have been developed or even marketed. Therefore, the important position of heterocyclic chemistry in the pesticides market is supposed to remain in the following decades.

This Special Issue of Molecules invites researchers to contribute original research papers or reviews in the field of design, synthesis, bioactivity, mechanism of action, and so on of heterocyclic pesticides.

Prof. Dr. Pei Li
Guest Editor

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Keywords

  • heterocyclic chemistry
  • heterocyclic pesticides
  • design
  • synthesis
  • bioactivity
  • mechanism of action

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Published Papers (7 papers)

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Research

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11 pages, 4068 KiB  
Article
Synthesis, Structure and Antibacterial Activity of Two Novel Coordination Polymers Based on N,N′-bis(4-carbozvlbenzvl)-4-aminotoluene and Heterocyclic Ligand against S. aureus
by Ziyun Wang, Lun Zhao, Hongwei Jing, Guanying Song and Jiayu Li
Molecules 2024, 29(9), 1990; https://doi.org/10.3390/molecules29091990 - 26 Apr 2024
Viewed by 825
Abstract
As the use of antibiotics increases, the increasing resistance of bacteria is the main reason for the reduced efficiency of antibacterial drugs, making the research of new antibacterial materials become new hot spot. In this article, two novel coordination polymers (CPs), namely, [Cd [...] Read more.
As the use of antibiotics increases, the increasing resistance of bacteria is the main reason for the reduced efficiency of antibacterial drugs, making the research of new antibacterial materials become new hot spot. In this article, two novel coordination polymers (CPs), namely, [Cd2(L)2(bibp)2]n (1) and [Ni(L)(bib)]n (2), where H2L = N,N′-bis(4-carbozvlbenzvl)-4-aminotoluene, bibp = 4,4′-bis(imidazol-1-yl)biphenyl, and bib = 1,3-bis(1-imidazoly)benzene, have been synthesized under solvothermal and hydrothermal condition. Structural clarification was performed through infrared spectrum and single-crystal X-ray diffraction analysis, while thermal analysis and XRD technology were used for the performance assessment of compounds 1 and 2. In addition, antibacterial performance experiments showed that compounds 1 and 2 have certain selectivity in their antibacterial properties and have good antibacterial properties against S. aureus. As the concentration of the compound increases, the inhibitory effect gradually strengthens, and when the concentration of the compound reaches 500 μg/mL and 400 μg/mL, the concentration of the S. aureus solution no longer increases and has been completely inhibited. Full article
(This article belongs to the Special Issue Advances of Heterocyclic Chemistry with Antibacterial and Antifungal Activity)
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13 pages, 1645 KiB  
Article
Synthesis, Antifungal, and Antibacterial Activities of Novel Benzoylurea Derivatives Containing a Pyrimidine Moiety
by Jiansong An, Wenjun Lan, Qiang Fei, Pei Li and Wenneng Wu
Molecules 2023, 28(18), 6498; https://doi.org/10.3390/molecules28186498 - 7 Sep 2023
Cited by 2 | Viewed by 1354
Abstract
To explore more efficient and less toxic antibacterial and antifungal pesticides, we utilized 2,6-difluorobenzamide as a starting material and ultimately synthesized 23 novel benzoylurea derivatives containing a pyrimidine moiety. Their structures were characterized and confirmed by 1H NMR, 13C NMR, 19 [...] Read more.
To explore more efficient and less toxic antibacterial and antifungal pesticides, we utilized 2,6-difluorobenzamide as a starting material and ultimately synthesized 23 novel benzoylurea derivatives containing a pyrimidine moiety. Their structures were characterized and confirmed by 1H NMR, 13C NMR, 19F NMR, and HRMS. The bioassay results demonstrated that some of the title compounds exhibited moderate to good in vitro antifungal activities against Botrytis cinerea in cucumber, Botrytis cinerea in tobacco, Botrytis cinerea in blueberry, Phomopsis sp., and Rhizoctonia solani. Notably, compounds 4j and 4l displayed EC50 values of 6.72 and 5.21 μg/mL against Rhizoctonia solani, respectively, which were comparable to that of hymexazol (6.11 μg/mL). Meanwhile, at 200 and 100 concentrations, the target compounds 4a–4w exhibited lower in vitro antibacterial activities against Xanthomonas oryzae pv. oryzicola and Xanthomonas citri subsp. citri, respectively, compared to those of thiodiazole copper. Furthermore, the molecular docking simulation demonstrated that compound 4l formed hydrogen bonds with SER-17 and SER-39 of succinate dehydrogenase (SDH), providing a possible explanation for the mechanism of action between the target compounds and SDH. This study represents the first report on the antifungal and antibacterial activities of novel benzoylurea derivatives containing a pyrimidine moiety. Full article
(This article belongs to the Special Issue Advances of Heterocyclic Chemistry with Antibacterial and Antifungal Activity)
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14 pages, 2996 KiB  
Article
Design, Catalyst-Free Synthesis of New Novel α-Trifluoromethylated Tertiary Alcohols Bearing Coumarins as Potential Antifungal Agents
by Shengfei Jiang, Guoyu Yang, Lijun Shi, Liangxin Fan, Zhenliang Pan, Caixia Wang, Xiaodan Chang, Bingyi Zhou, Meng Xu, Lulu Wu and Cuilian Xu
Molecules 2023, 28(1), 260; https://doi.org/10.3390/molecules28010260 - 28 Dec 2022
Cited by 4 | Viewed by 1784
Abstract
A new method for the synthesis of α-trifluoromethylated tertiary alcohols bearing coumarins is described. The reaction of 3-(trifluoroacetyl)coumarin and pyrrole provided the target compounds with high yields under catalyst-free, mild conditions. The crystal structure of compound 3fa was investigated by X-ray diffraction analysis. [...] Read more.
A new method for the synthesis of α-trifluoromethylated tertiary alcohols bearing coumarins is described. The reaction of 3-(trifluoroacetyl)coumarin and pyrrole provided the target compounds with high yields under catalyst-free, mild conditions. The crystal structure of compound 3fa was investigated by X-ray diffraction analysis. The biological activities, such as in vitro antifungal activity of the α-trifluoromethylated tertiary alcohols against Fusarium graminearum, Fusarium oxysporum, Fusarium moniliforme, Rhizoctonia solani Kuhn, and Phytophthora parasitica var nicotianae, were investigated. The bioassay results indicated that compounds 3ad, 3gd, and 3hd showed broad-spectrum antifungal activity in vitro. Compound 3cd exhibited excellent fungicidal activity against Rhizoctonia solani Kuhn, with an EC50 value of 10.9 μg/mL, which was comparable to that of commercial fungicidal triadimefon (EC50 = 6.1 μg/mL). Furthermore, molecular docking study suggested that 3cd had high binding affinities with 1W9U, like argifin. Full article
(This article belongs to the Special Issue Advances of Heterocyclic Chemistry with Antibacterial and Antifungal Activity)
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13 pages, 1186 KiB  
Article
Establishment of an LC-MS/MS Method for the Determination of 45 Pesticide Residues in Fruits and Vegetables from Fujian, China
by Kunming Zheng, Xiaoping Wu, Jiannan Chen, Jinxing Chen, Wenhao Lian, Jianfeng Su and Lihong Shi
Molecules 2022, 27(24), 8674; https://doi.org/10.3390/molecules27248674 - 8 Dec 2022
Cited by 13 | Viewed by 2255
Abstract
Pesticide residues in food have become an important factor seriously threatening human health. Therefore, this study was conducted to determine the pesticide residues in fruits and vegetables commonly found in Fujian, China, with the aim of constructing a simple and rapid method for [...] Read more.
Pesticide residues in food have become an important factor seriously threatening human health. Therefore, this study was conducted to determine the pesticide residues in fruits and vegetables commonly found in Fujian, China, with the aim of constructing a simple and rapid method for pesticide residue monitoring. We collected 5607 samples from local markets and analyzed them for the presence of 45 pesticide residues. A fast, easy, inexpensive, effective, robust, and safe (QuEChERS) multi-residue extraction method followed by liquid chromatography equipped with triple-quadrupole mass spectrometry (LC-MS/MS) was successfully established. This 12-min-long analytical method detects and quantifies pesticide residues with acceptable validation performance parameters in terms of sensitivity, selectivity, linearity, the limit of quantification, accuracy, and precision. The linear range of the calibration curves ranged from 5 to 200 mg/L, the limits of detection for all pesticides ranged from 0.02 to 1.90 μg/kg, and the limits of quantification for the pesticides were 10 μg/kg. The recovery rates for the three levels of fortification ranged from 72.0% to 118.0%, with precision values (expressed as RSD%) less than 20% for all of the investigated analytes. The results showed that 726 (12.95%) samples were contaminated with pesticide residues, 94 (1.68%) samples exceeded the maximum residue limit (MRL) of the national standard (GB 2763-2021, China), 632 (11.23%) samples were contaminated with residues below the MRL, and 4881 (87.05%) samples were pesticide residue-free. In addition, the highest number of multiple pesticide residues was observed in bananas and peppers, which were contaminated with acetamiprid, imidacloprid, pyraclostrobin, and thiacloprid. Full article
(This article belongs to the Special Issue Advances of Heterocyclic Chemistry with Antibacterial and Antifungal Activity)
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10 pages, 262 KiB  
Article
Investigation and Analysis of Pesticide Residues in Four Common Vegetables and Risk Assessment of Dietary Exposure in Ceramic Capital, China
by Xingang Meng, Lu Wang, Niao Wang, Luting Chen and Qian Huang
Molecules 2022, 27(19), 6562; https://doi.org/10.3390/molecules27196562 - 4 Oct 2022
Cited by 5 | Viewed by 1890
Abstract
In order to understand the basic situation of pesticide residues in vegetables in China’s porcelain capital, four kinds of common vegetables on the market were selected in this study for detection and analysis of pesticide residues. The pesticide residues in vegetables were analyzed [...] Read more.
In order to understand the basic situation of pesticide residues in vegetables in China’s porcelain capital, four kinds of common vegetables on the market were selected in this study for detection and analysis of pesticide residues. The pesticide residues in vegetables were analyzed through sample selection, optimization of instrument and equipment conditions, and comparison of detection pass rates. The sampling locations were common vegetables purchasing places such as large and medium-sized supermarkets. QuEChERS method was used as the sample pretreatment, and gas chromatography (GC-MS/MS) was used for quantitative analysis. Finally, the exposure risk of pesticides was assessed according to the test results. The results showed that all the pesticides were detected in four kinds of vegetables, but the detected pesticides did not exceed the national standard (GB 2763-2014, China). Moreover, the target risk coefficient (THQ) and risk index (HI) values of four vegetables were less than one, indicating that the combined and toxic effect of pesticide residual mixed contamination was smaller in four vegetables. Therefore, there was no significant harm from people using these vegetables. Full article
(This article belongs to the Special Issue Advances of Heterocyclic Chemistry with Antibacterial and Antifungal Activity)

Review

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28 pages, 8079 KiB  
Review
D-Hexopyranosides with Vicinal Nitrogen-Containing Functionalities
by Jana Pospíšilová, Daniel Toman, Tomáš Ručil and Petr Cankař
Molecules 2024, 29(15), 3465; https://doi.org/10.3390/molecules29153465 - 24 Jul 2024
Viewed by 569
Abstract
Various substituted D-hexopypyranosides units with nitrogen-containing functionalities are present in many important natural compounds and pharmaceutical substances. Since their complex structural diversity contributes to a broad spectrum of biological functions and activities, these derivatives are frequently studied. This review covers syntheses of D-hexopyranosides [...] Read more.
Various substituted D-hexopypyranosides units with nitrogen-containing functionalities are present in many important natural compounds and pharmaceutical substances. Since their complex structural diversity contributes to a broad spectrum of biological functions and activities, these derivatives are frequently studied. This review covers syntheses of D-hexopyranosides with vicinal nitrogen-containing functionalities since the 1960s, when the first articles emerged. The syntheses are arranged according to the positions of substitutions, to form a relative configuration of vicinal functionalities, and synthetic methodologies. Full article
(This article belongs to the Special Issue Advances of Heterocyclic Chemistry with Antibacterial and Antifungal Activity)
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14 pages, 604 KiB  
Review
Research Progress on Benzimidazole Fungicides: A Review
by Song Bai, Miaohe Zhang, Shouying Tang, Miao Li, Rong Wu, Suran Wan, Lijun Chen, Xian Wei and Feifei Li
Molecules 2024, 29(6), 1218; https://doi.org/10.3390/molecules29061218 - 8 Mar 2024
Cited by 4 | Viewed by 2947
Abstract
Benzimidazole fungicides are a class of highly effective, low-toxicity, systemic broad-spectrum fungicides developed in the 1960s and 1970s, based on the fungicidal activity of the benzimidazole ring structure. They exhibit biological activities including anticancer, antibacterial, and antiparasitic effects. Due to their particularly outstanding [...] Read more.
Benzimidazole fungicides are a class of highly effective, low-toxicity, systemic broad-spectrum fungicides developed in the 1960s and 1970s, based on the fungicidal activity of the benzimidazole ring structure. They exhibit biological activities including anticancer, antibacterial, and antiparasitic effects. Due to their particularly outstanding antibacterial properties, they are widely used in agriculture to prevent and control various plant diseases caused by fungi. The main products of benzimidazole fungicides include benomyl, carbendazim, thiabendazole, albendazole, thiophanate, thiophanate-methyl, fuberidazole, methyl (1-{[(5-cyanopentyl)amino]carbonyl}-1H-benzimidazol-2-yl) carbamate, and carbendazim salicylate. This article mainly reviews the physicochemical properties, toxicological properties, disease control efficacy, and pesticide residue and detection technologies of the aforementioned nine benzimidazole fungicides and their main metabolite (2-aminobenzimidazole). On this basis, a brief outlook on the future research directions of benzimidazole fungicides is presented. Full article
(This article belongs to the Special Issue Advances of Heterocyclic Chemistry with Antibacterial and Antifungal Activity)
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