Synthesis and fungicidal activity of methyl (E)-1-(2-((E)-2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)-2-(1-arylidene)hydrazine-1-carboxylates †‡

Jia, Changqing; Yin, Fahong; Zhang, Li; Du, Shijie; Li, Jiaqi; Xiao, Yumei; Qin, Z. H.

doi:10.1007/s11030-021-10187-6

Cited by 4 publications

(4 citation statements)

References 22 publications

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“…Antifungal Activity Test . The in vitro antifungal activities of the title compound against eight phytopathogenic fungi using the mycelia growth inhibition method according as described previously [26]. Difenoconazole was chosen as the positive control.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and biological activity of sulfoximine derivatives

Liu

Wang

Yong

et al. 2021

Journal of Heterocyclic Chem

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In order to discover new pesticides with novel modes of action and further study the sulfoximine scaffolds, 30 novel sulfoximine derivatives were designed, synthesized, and evaluated for their insecticidal and antifungal activities. The preliminary bioassay results showed that the insecticidal activity of target compounds was weak, only I-12 displayed 80.39% larvicidal activity against Nilaparvata lugen, slightly lower than sulfoxaflor (97.87%) at 100 μg/ml. However, most of the compounds also displayed fair to good fungicidal activities against eight representative phytopathogenic fungi, and I-5 showed slightly lower fungicidal activity against Sclerotinia scleotiorum than the control drug difenoconazole (2.26 μg/ml) with an EC 50 of 8.75 μg/ml. The structure-activity relationship showed that the compound exhibited better antifungal activity when the R was 2.4-disubstituted phenyl. Our studies suggested that sulfoximine scaffolds may also have potential plant-fungal activity. This is the first report on the use of sulfoximide scaffolds as fungicides.

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Section: Methodsmentioning

confidence: 99%

Design, synthesis, and biological activity of sulfoximine derivatives

Liu

Wang

Yong

et al. 2021

Journal of Heterocyclic Chem

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“…The promising compound 28 exhibited not only good in vitro fungicidal activity against S. sclerotiorum (EC 50 = 3.96 μg/mL) but also remarkable in vivo fungicidal activity against rice blast fungus and powdery mildew of cucumber . Another lead compound 29 displayed comparable fungicidal activity against Puccinia polysora (inhibition = 80%) and wheat white powder (inhibition = 88%) to commercial fungicides kresoxim-methyl (inhibition = 80% and 98%, respectively) in pot experiments …”

Section: β-Methoxyacrylate Derivatives As Pesticidesmentioning

confidence: 98%

“…49 Another lead compound 29 displayed comparable fungicidal activity against Puccinia polysora (inhibition = 80%) and wheat white powder (inhibition = 88%) to commercial fungicides kresoxim-methyl (inhibition = 80% and 98%, respectively) in pot experiments. 50 The other groups reported some β-methoxyacrylate analogs with different substitutions on the benzene ring. Fluorinecontaining compound 30 exhibited excellent fungicidal activities against E. graminis with 85% control at 0.39 μg/ mL, which was much better than azoxystrobin (30%) and pyraclostrobin (70%).…”

Section: β-Methoxyacrylate Derivatives As Pesticidesmentioning

confidence: 99%

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc₁ Inhibitors for Novel Pesticide Discovery

Luo

Ning

Rao

2022

J. Agric. Food Chem.

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β-Methoxyacrylate derivatives represent a new class of pesticides, which have attracted increasing attention owing to their unique structure, broad biological activity, and unique mechanisms of action. They inhibit mitochondrial respiration via preventing electron transfer at the Qo site of the cytochrome bc 1 complex and thus are identified as cyt bc 1 inhibitors. A variety of βmethoxyacrylate derivatives have been reported by many research groups for discovery of novel pesticides with improved expected activities. This review focuses on development of β-methoxyacrylate derivatives with great significance as pesticides such as fungicides, acaricides, insecticides, herbicides, and antiviral agents. In addition, the structure−activity relationships (SARs) of βmethoxyacrylate derivatives are summarized. Moreover, the cause of resistance to β-methoxyacrylate fungicides and some solutions are also introduced. Finally, the development trend of β-methoxyacrylate derivatives as pesticides is explored. We hope the review will give a guide to develop novel β-methoxyacrylate pesticides in the future.

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“…For example, representative fungicides bearing a hydrazide fragment have been successfully constructed and employed as agrochemical fungicides (Figure ). − Therefore, we propose that introducing a hydrazide fragment into 3-hydroxyflavones may produce novel antifungal agents with biological activity (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Acethydrazide-Containing Flavonol Derivatives as Potential Antifungal Agents

Chen,

Jiang,

Tong

et al. 2024

J. Agric. Food Chem.

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In this study, a series of novel hydrazide-containing flavonol derivatives was designed, synthesized, and evaluated for antifungal activity. In the in vitro antifungal assay, most of the target compounds exhibited potent antifungal activity against seven tested phytopathogenic fungi. In particular, compound C32 showed the best antifungal activity against Rhizoctonia solani (EC 50 = 0.170 μg/mL), outperforming carbendazim (EC 50 = 0.360 μg/mL) and boscalid (EC 50 = 1.36 μg/mL). Compound C24 exhibited excellent antifungal activity against Valsa mali, Botrytis cinerea, and Alternaria alternata with EC 50 values of 0.590, 0.870, and 1.71 μg/ mL, respectively. The in vivo experiments revealed that compounds C32 and C24 were potential novel agricultural antifungals. 3D quantitative structure−activity relationship (3D-QSAR) models were used to analyze the structure−activity relationships of these compounds. The analysis results indicated that introducing appropriate electronegative groups at position 4 of a benzene ring could effectively improve the anti-R. solani activity. In the antifungal mechanism study, scanning electron microscopy and transmission electron microscopy analyses revealed that C32 disrupted the normal growth of hyphae by affecting the structural integrity of the cell membrane and cellular respiration. Furthermore, compound C32 exhibited potent succinate dehydrogenase (SDH) inhibitory activity (IC 50 = 8.42 μM), surpassing that of the SDH fungicide boscalid (IC 50 = 15.6 μM). The molecular dynamics simulations and docking experiments suggested that compound C32 can occupy the active site and form strong interactions with the key residues of SDH. Our findings have great potential for aiding future research on plant disease control in agriculture.

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Synthesis and fungicidal activity of methyl (E)-1-(2-((E)-2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)-2-(1-arylidene)hydrazine-1-carboxylates †‡

Cited by 4 publications

References 22 publications

Design, synthesis, and biological activity of sulfoximine derivatives

Design, synthesis, and biological activity of sulfoximine derivatives

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc₁ Inhibitors for Novel Pesticide Discovery

Discovery of Novel Acethydrazide-Containing Flavonol Derivatives as Potential Antifungal Agents

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Synthesis and fungicidal activity of methyl (E)-1-(2-((E)-2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)-2-(1-arylidene)hydrazine-1-carboxylates †‡

Cited by 4 publications

References 22 publications

Design, synthesis, and biological activity of sulfoximine derivatives

Design, synthesis, and biological activity of sulfoximine derivatives

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc1 Inhibitors for Novel Pesticide Discovery

Discovery of Novel Acethydrazide-Containing Flavonol Derivatives as Potential Antifungal Agents

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Product

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Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc₁ Inhibitors for Novel Pesticide Discovery