Antifungal Exploration of Quinoline Derivatives against Phytopathogenic Fungi Inspired by Quinine Alkaloids

Chen, Yong-Jia; Ma, Kun-Yuan; Du, Shanshan; Zhang, Zhijun; Wu, Tian‐Lin; Sun, Yu; Liu, Ying‐Qian; Yin, Xiaoyi; Zhou, Rui; Yan, Yin-Fang; Wang, Ren-Xuan; He, Yi; Chu, Qing-Ru; Tang, Chong

doi:10.1021/acs.jafc.1c05677

Cited by 30 publications

(39 citation statements)

References 42 publications

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“… On the other hand, for the fungicidal acethydrazide compounds reported in the literature, the plasma membrane contraction and separation from the cell wall in the treated fungal cells could be clearly found by TEM observation, while the specific target was unclear (Figure ). In this project, it was also found that the plasma membrane was shrunk seriously and separated from the cell wall (Figure ). Therefore, transcriptomics and metabolomics measurements were performed to further elucidate the mechanism of action of acethydrazide compound C4 .…”

Section: Resultsmentioning

confidence: 66%

“…In terms of agricultural fungicidal activity, for example, Wang’s group reported benzoic hydrazides ( 1 ) containing a 1,2,3-triazole group as potential SDH inhibitors, Yang and co-workers synthesized pyrazole hydrazides ( 2 ) bearing a 1,3,4-oxadiazole core as agrochemicals against plant fungus and Ye’s group prepared 1,2,3-triazole hydrazide derivatives ( 3 ) exhibiting anti-phytopathogenic activity . Similarly, other literature has also successively reported the application of hydrazide structures controlling agricultural pathogens, − such as compounds 4 – 6 listed in Figure .…”

Section: Introductionmentioning

confidence: 99%

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Discovery of Aryloxy-, Arylthio-, and Arylamino-Containing Acethydrazides as Fungicidal Agents

Fang

Chen

Liu

et al. 2022

J. Agric. Food Chem.

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The development of new green fungicides is an effective way to solve the resistance of agricultural pathogens and plays an important role in promoting high-quality and sustainable development of modern agriculture. In this project, a series of aryloxy-, arylthio-, and arylamino-containing acethydrazide derivatives were designed, synthesized, and characterized by 1 H nuclear magnetic resonance (NMR), 13 C NMR, and high-resolution mass spectrometry (HRMS). The fungicidal bioassays indicated that some compounds showed excellent and broad-spectrum fungicidal activity, and the structure−activity relationship was discussed. The in vivo fungicidal activity demonstrated that compounds C4 and D8 exhibited good preventative effects against Fusarium graminearum infecting wheat leaves, of which the preventative activity of compound D8 was almost equal to that of the positive agents. Transmission electron microscopy (TEM) observation revealed that the plasma membrane in the C4-treated F. graminearum hyphal cells was severely contracted and separated with the cell wall, coupling with the visible lysosomes and the disappeared cytoplasm and organelles, which may be the reasons for the shriveled and even ruptured hyphae observed by scanning electron microscopy (SEM). Subsequently, transcriptomics and metabolomics were performed to further elucidate the fungicidal mechanism. The regulatory networks of differential genes and metabolites in plasma membrane-related sphingolipid metabolism, linoleic acid metabolism, α-linoleic acid metabolism, and arachidonic acid metabolism were constructed and elaborated. Additionally, preliminary investigation of seeding growth suggested that compounds C4 and D8 may have different degrees of influence on the growth indicators of wheat seedlings; however, this effect may be negligible as the plant grows.

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Section: Resultsmentioning

confidence: 66%

Section: Introductionmentioning

confidence: 99%

Discovery of Aryloxy-, Arylthio-, and Arylamino-Containing Acethydrazides as Fungicidal Agents

Fang

Chen

Liu

et al. 2022

J. Agric. Food Chem.

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“…The change in permeability of S. sclerotiorum membrane treated with compound 6c 2 was determined by a conductivity method 41 . The mycelial disks of S. sclerotiorum (5 mm) were placed in 20.0 mL of Potato Dextrose Broth ( PDB) liquid medium at 27 °C and shaken at 140 rpm to culture for 4 days.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and antifungal activities of novel sulfoximine derivatives for plant protection

Liu

Zhao

et al. 2023

Pest Management Science

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BACKGROUND: Fungicides play a significant role in the integrated management of plant pathogens. However, the irrational application of fungicides with similar structures has led to development of cross-resistance, therefore there is a need to seek novel fungicides with new structures. RESULTS: Twenty-eight novel sulfoximine derivatives incorporating nitroguanidine moieties were designed, synthesized, and evaluated as antifungal agents. The bioassay results indicated that most of the synthesized compounds displayed excellent fungicidal activities against Sclerotinia sclerotiorum, Rhizoctonia solani, Fusarium graminearum, and Pyricularia grisea. Among these, compounds 6c 4 , 6c 5 , and 6c 6 exhibited remarkable fungicidal activities against P. grisea, with EC 50 values of 1.28, 1.17, and 1.68 ∼g mL −1 , respectively. In addition, compound 6c 2 displayed the most potent activity against S. sclerotiorum (EC 50 = 3.64 ∼g mL −1 ). Further in vivo fungicidal activity screening against S. sclerotiorum demonstrated that the protective and curative effects of compound 6c 2 were 98.1% and 91.3% at 25 ∼g mL −1 , respectively, comparable to that of boscalid (94.4%, 89.6%). The preliminary mechanism study found that the hyphae of S. sclerotiorum treated with compound 6c 2 was abnormal with mycelial collapse and membrane permeability increase. The present findings can help to develop new fungicides for crop protection.CONCLUSION: Novel sulfoximine derivatives containing nitroguanidine possess potential antifungal activity, and the unique structure may offer an alternative option for fungicide development in the future.

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“…DMSO (1%) in 10 mL water was used as a blank control. All treated samples were placed in a light incubator at 25 °C and 100% relative humidity for 9 d. All assays were performed at least in triplicate using conventional methods [ 51 ].…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, Fungicidal and Insecticidal Activities of Novel Diamide Compounds Combining Pyrazolyl and Polyfluoro-Substituted Phenyl into Alanine or 2-Aminobutyric Acid Skeletons

Feng²,

Liu³

et al. 2023

Molecules

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Thirty novel diamide compounds combining pyrazolyl and polyfluoro-substituted phenyl groups into alanine or 2-aminobutyric acid skeletons were designed and synthesized with pyflubumide as the lead compound to develop potent and environmentally friendly pesticides. The preliminary bioassay results indicated that the new compounds containing the para-hexa/heptafluoroisopropylphenyl moiety exhibit fungicidal, insecticidal, and acaricidal activities. This is the first time that the para-hexa/heptafluoroisopropylphenyl group is a key fragment of the fungicidal activity of new N-phenyl amide compounds. Most of the target compounds exhibited moderate to good insecticidal activity against Aphis craccivora at a concentration of 400 μg/mL, and some showed moderate activity at a concentration of 200 μg/mL; in particular, compounds I-4, II-a-10, and III-26 displayed higher than 78% lethal rates at 200 μg/mL. Compound II-a-14 exhibited a 61.1% inhibition at 200 μg/mL for Tetranychus cinnabarinus. In addition, some of the target compounds exhibited good insecticidal activities against Plutella xylostella at a concentration of 200 μg/mL; the mortalities of compounds I-1, and II-a-15 were 76.7% and 70.0%, respectively. Preliminary analysis of the structure–activity relationship (SAR) indicated that the insecticidal and acaricidal activities varied significantly depending on the type of substituent and substitution pattern. The fungicidal activity results showed that compounds I-1, II-a-10, II-a-17, and III-26 exhibited good antifungal effects. Enzymatic activity experiments and in vivo efficacy of compound II-a-10 were conducted and discussed.

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Antifungal Exploration of Quinoline Derivatives against Phytopathogenic Fungi Inspired by Quinine Alkaloids

Cited by 30 publications

References 42 publications

Discovery of Aryloxy-, Arylthio-, and Arylamino-Containing Acethydrazides as Fungicidal Agents

Discovery of Aryloxy-, Arylthio-, and Arylamino-Containing Acethydrazides as Fungicidal Agents

Design, synthesis, and antifungal activities of novel sulfoximine derivatives for plant protection

Design, Synthesis, Fungicidal and Insecticidal Activities of Novel Diamide Compounds Combining Pyrazolyl and Polyfluoro-Substituted Phenyl into Alanine or 2-Aminobutyric Acid Skeletons

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