Design, synthesis, pharmacophore modeling, and molecular docking of some novel chloroacetamide derivatives as herbicidal agents

IF 5.2 2区 农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY
Saad R. El-Zemity, Kareem E. E. Esmaiel, Mohamed E. I. Badawy
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引用次数: 0

Abstract

Background

The discovery of new lead compounds with desired properties and biological activity is an excellent challenge in pesticide chemistry. Chloroacetamide are an important class of synthetic herbicides.

Results

To explore the herbicidal activity of chloroacetamides, several new chloroacetamide derivatives have been designed, and synthesized. The compounds have been described by forming Schiff bases followed by chloroacetylation of imines. The herbicidal activity as a chlorophyll inhibition was evaluated against two broadleaf weeds (Chenopodium album and Anagallis arvensis) and two grass weeds (Lolium temulentum and Echinochloa crus-galli) in comparison with acetochlor as a standard herbicide. 1H-NMR, 13C-NMR and mass spectroscopic analyses confirmed the chemical structures of the synthesized compounds. Several compounds have demonstrated highly potent herbicidal activity compared to the standard herbicide acetochlor. Some of them have been described as the most effective against weeds tested, such as compounds 5b and 18b. Molecular docking to the active sites of Very Long Chain Fatty Acid Synthase (VLCFAS) has indicated that most compounds are low-energy binding agents and show high affinity for the active pocket.

Conclusion

Novel herbicides may be discovered by combining chloroacetamide derivatives with these existing lead structures.

Graphical Abstract

作为除草剂的一些新型氯乙酰胺衍生物的设计、合成、药效学建模和分子对接
背景发现具有所需性质和生物活性的新先导化合物是农药化学领域的一项巨大挑战。为了探索氯乙酰胺的除草活性,我们设计并合成了几种新的氯乙酰胺衍生物。这些化合物是通过形成希夫碱,然后对亚胺进行氯乙酰化而得到的。与标准除草剂乙草胺相比,这些化合物对两种阔叶杂草(Chenopodium album 和 Anagallis arvensis)和两种禾本科杂草(Lolium temulentum 和 Echinochloa crus-galli)的除草活性(叶绿素抑制)进行了评估。1H-NMR 、13C-NMR 和质谱分析证实了合成化合物的化学结构。与标准除草剂乙草胺相比,有几种化合物具有很强的除草活性。其中一些化合物(如化合物 5b 和 18b)被认为是对测试杂草最有效的化合物。与超长链脂肪酸合成酶(VLCFAS)活性位点的分子对接表明,大多数化合物都是低能结合剂,对活性口袋具有很高的亲和力。
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来源期刊
Chemical and Biological Technologies in Agriculture
Chemical and Biological Technologies in Agriculture Biochemistry, Genetics and Molecular Biology-Biotechnology
CiteScore
6.80
自引率
3.00%
发文量
83
审稿时长
15 weeks
期刊介绍: Chemical and Biological Technologies in Agriculture is an international, interdisciplinary, peer-reviewed forum for the advancement and application to all fields of agriculture of modern chemical, biochemical and molecular technologies. The scope of this journal includes chemical and biochemical processes aimed to increase sustainable agricultural and food production, the evaluation of quality and origin of raw primary products and their transformation into foods and chemicals, as well as environmental monitoring and remediation. Of special interest are the effects of chemical and biochemical technologies, also at the nano and supramolecular scale, on the relationships between soil, plants, microorganisms and their environment, with the help of modern bioinformatics. Another special focus is the use of modern bioorganic and biological chemistry to develop new technologies for plant nutrition and bio-stimulation, advancement of biorefineries from biomasses, safe and traceable food products, carbon storage in soil and plants and restoration of contaminated soils to agriculture. This journal presents the first opportunity to bring together researchers from a wide number of disciplines within the agricultural chemical and biological sciences, from both industry and academia. The principle aim of Chemical and Biological Technologies in Agriculture is to allow the exchange of the most advanced chemical and biochemical knowledge to develop technologies which address one of the most pressing challenges of our times - sustaining a growing world population. Chemical and Biological Technologies in Agriculture publishes original research articles, short letters and invited reviews. Articles from scientists in industry, academia as well as private research institutes, non-governmental and environmental organizations are encouraged.
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