Design, Synthesis, and Herbicidal Evaluation of Novel Uracil Derivatives Containing 1,3,4‐Thiadiazolyl Moiety

He, Liping; Wu, Ying‐Ying; Zhang, Hanyun; Manyun, Liu; Shi, De‐Qing

doi:10.1002/jhet.2160

Cited by 7 publications

(3 citation statements)

References 9 publications

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“…Three dicotyledonous weeds, AR, EP and AT, and three monocotyledonous weeds, DS, SV and EC were chosen to evaluate the herbicidal efficacy of all title compounds using previously reported methods 13,45,46 …”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and herbicidal activity of novel phenoxypyridine derivatives containing natural product coumarin

Zhao

Wang

Peng

et al. 2021

Pest Management Science

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BACKGROUND In recent years, protoporphyrinogen oxidase (PPO, EC 1.3.3.4) inhibitors have been widely studied as important agricultural herbicides. Our research focused on the design and synthesis of novel PPO inhibitor herbicides, through linking of a diphenylether pyridine bioisostere structure to substituted coumarins, which aims to enhance environmental and crop safety while retaining high efficacy. RESULTS A total of 21 compounds were synthesized via acylation reactions and all compounds were characterized using infrared, 1H NMR, 13C NMR, and high‐resolution mass spectra. The respective configurations of compounds IV‐6 and IV‐12 were also confirmed using single crystal X‐ray diffraction. The bioassay results showed that the title compounds displayed notable herbicidal activity, particularly compound IV‐6 which displayed better herbicidal activity in greenhouse and field experiments, crop selectivity and safety for cotton and soybean compared with the commercial herbicide oxyfluorfen. CONCLUSION The work revealed that compound IV‐6 deserves further attention as a candidate structure for a novel and safe herbicide. © 2021 Society of Chemical Industry.

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Section: Methodsmentioning

confidence: 99%

Design, synthesis, and herbicidal activity of novel phenoxypyridine derivatives containing natural product coumarin

Zhao

Wang

Peng

et al. 2021

Pest Management Science

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“…They had a wide range of biological features, including bactericidal, − antifungal, insecticidal, , and anticancer properties in medicine. These compounds not only functioned as effective fungicides but also served as vital plant growth regulators and herbicides, among other chemicals. Commercially available 1,3,4-thiadiazole agricultural fungicides included thiazole zinc, bismerthiazol, thiamethoxam copper, thiessen copper, and others.…”

Section: Introductionmentioning

confidence: 99%

Antifungal Activity of Novel Indole Derivatives Containing 1,3,4-Thiadiazole

He,

Hu,

Xing

et al. 2024

J. Agric. Food Chem.

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In this study, 24 indole derivatives containing 1,3,4-thiadiazole were discovered and synthesized. The target compounds' antifungal efficacy against 14 plant pathogenic fungal pathogens was then determined in vitro. With an EC 50 value of 2.7 μg/mL, Z2 demonstrated the highest level of bioactivity among them against Botrytis cinerea (B.c.), exceeding the concentrations of the control prescription drugs azoxystrobin (Az) (EC 50 = 14.5 μg/mL) and fluopyram (Fl) (EC 50 = 10.1 μg/mL). Z2 underwent in vivo testing on blueberry leaves in order to evaluate its usefulness in real-world settings. A reasonable protective effect was obtained with a control effectiveness of 93.0% at 200 μg/mL, which was superior to those of Az (83.0%) and Fl (52.0%). At 200 μg/mL, this chemical had an efficacy of 84.0% in terms of curative efficacy. These figures outperformed those of Az (69.0%) and Fl (48.0%). Scanning electron microscopy (SEM) experiments and light microscopy experiments showed that Z2 altered the integrity of the cell wall and cell membrane of the pathogenic fungus B.c., which led to an increase in the content of malondialdehyde (MDA), cellular leakage, and cellular permeability. Enzyme activity assays and molecular docking studies indicated that Z2 could act as a potential succinate dehydrogenase inhibitor (SDHI). It was hypothesized that Z2 could cause disruption of mycelial cell membranes, which in turn leads to mycelial death. According to the research, indole derivatives containing 1,3,4-thiadiazole were expected to evolve into new fungicides due to their significant antifungal effects on plant fungi.

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“…1,3,4-thiadiazole derivatives were widely used as pesticides in agrochemical chemistry and studied for years due to their excellent biological activities, including antifungal [ 52 , 53 ], insecticidal [ 54 ], acaricidal [ 54 ], antibacterial [ 55 ], and herbicidal activities [ 56 ]. Heterocyclic thioether compounds also possess high antifungal activities [ 57 ], and the thioether-bound 1,3,4-thiadiazole scaffold is an important pharmacophore [ 58 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

et al. 2022

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A series of novel indole Schiff base derivatives (2a–2t) containing a 1,3,4-thiadiazole scaffold modified with a thioether group were synthesized, and their structures were confirmed using FT-IR, 1H NMR, 13C NMR, and HR-MS. In addition, the antifungal activity of synthesized indole derivatives was investigated against Fusarium graminearum (F. graminearum), Fusarium oxysporum (F. oxysporum), Fusariummoniliforme (F.moniliforme), Curvularia lunata (C. lunata), and Phytophthora parasitica var. nicotiana (P. p. var. nicotianae) using the mycelium growth rate method. Among the synthesized indole derivatives, compound 2j showed the highest inhibition rates of 100%, 95.7%, 89%, and 76.5% at a concentration of 500 μg/mL against F. graminearum, F. oxysporum, F.moniliforme, and P. p. var. nicotianae, respectively. Similarly, compounds 2j and 2q exhibited higher inhibition rates of 81.9% and 83.7% at a concentration of 500 μg/mL against C. lunata. In addition, compound 2j has been recognized as a potential compound for further investigation in the field of fungicides.

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Design, Synthesis, and Herbicidal Evaluation of Novel Uracil Derivatives Containing 1,3,4‐Thiadiazolyl Moiety

Cited by 7 publications

References 9 publications

Design, synthesis, and herbicidal activity of novel phenoxypyridine derivatives containing natural product coumarin

Design, synthesis, and herbicidal activity of novel phenoxypyridine derivatives containing natural product coumarin

Antifungal Activity of Novel Indole Derivatives Containing 1,3,4-Thiadiazole

Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

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