Synthesis and Fungicidal Activity of (E)-5-[1-(4-Phenyl-2-oxo-1-oxaspiro[4.5]dec-3-en-3-yl)ethylidene]-2-aminoimidazolin-4-one Derivatives

Zhao, Yu; Tang, Bo; Guan, Aiying; Wang, Weiwei; Zhang, Zhenhua; Wang, Mingan

doi:10.1055/s-0036-1588463

Cited by 6 publications

(14 citation statements)

References 18 publications

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“…The key intermediates 3 and 4 were synthesized following the manner in our previous studies by the reaction of 1 (24 mmol, 6.53 g) and 2 (25 mmol, 5.15 g). − …”

Section: Methodsmentioning

confidence: 99%

“…The intermediate 1 was obtained as a colorless solid, 13.42 g, yield 98% according to the previous protocol using (1-hydroxycyclohexyl)(phenyl)methanone (50 mmol, 10.20 g) and diketene (75 mmol, 6.30 g) as the starting materials. − …”

Section: Methodsmentioning

confidence: 99%

“…The compound 5 was obtained following the method in our previous papers − by the reactions of 3 (10 mmol, 4.60 g) with methyl iodide (15 mmol, 2.14 g). Compound 6 was synthesized by the same method using 4 as the raw material.…”

Section: Methodsmentioning

confidence: 99%

“…In the early stage of our research, the substrate-based approach was used to combine various pharmacophores such as spirocyclic butenolide and imidazolinone, and hundreds of compounds have been designed and synthesized including 5-[1-(2-oxo-4-phenyl-1-oxaspiro[4.5]dec-3-en-3-yl)ethylidene)]-2-aminoimidazolin-4-one derivatives. The evaluation of biological activity showed that some compounds have excellent fungicidal and insecticidal activities. − However, it was found that these 2-aminoimidazolinone derivatives have multiple tautomers in the solution, which make it difficult to characterize them and explore the structure–activity relationship. − During the process of structural modification of commercial fungicide fenamidone, it was found that the 3-position proton of imidazolinone was replaced by a benzyl group, and these compounds also showed excellent fungicidal activities . With the aim to find novel compounds with higher fungicidal activity and reduce the possibility of tautomerism, a series of novel 3-benzyl-5-[1-(2-oxo-4-phenyl-1-oxaspiro[4.5]dec-3-en-3-yl)ethylidene]-2-aminoimidazolin-4-one derivatives was designed and synthesized by introducing the benzyl group to the 3-position of the imidazolinone ring (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

“…Among these compounds, the intermediate 10 displayed the best protective activity with 70% control efficacy against P. cubensis at 100 μg/ mL. 27 After compound 10 was derivatized with various substituted amines, the in vivo fungicidal activities of the obtained compounds were obviously reduced. Comparison of the fungicidal activities of compounds having an N 3 -benzyl group with those of compounds having a non-N 3 -benzyl group proved that the introduction of N 3 -benzyl had significantly improved the fungicidal activities of this type of compound.…”

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confidence: 96%

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Design, Synthesis, and Fungicidal Activity of Novel Plant Elicitors Based on a Diversity-Oriented Synthesis Strategy

et al. 2022

J. Agric. Food Chem.

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The novel plant elicitors, 3-benzyl-5-[1-(2-oxo-4-phenyl-1-oxaspiro[4.5]dec-3-en-3-yl)ethylidene]-2-aminoimidazolin-4-one derivatives, were designed based on the diversity-oriented synthesis strategy and synthesized in four steps via the Knoevenagel condensation reaction as the key step. They were characterized by 1H NMR, 13C NMR, HR-ESI-MS, and X-ray diffraction. The position of the CN bond of Z- and E-configuration compounds was determined by X-ray diffraction. The in vivo fungicidal activity evaluation revealed that most of these compounds exhibited remarkable activities (100%) against Pseudoperonospora cubensis at 400 μg/mL, among which compound 8e still exhibited excellent protective activity with a 50% inhibition rate at 0.1 μg/mL. Because the in vitro effect on tested phytopathogens was poor, the mechanism to induce the immune responses and reinforce the resistance of cucumber against Botrytis cinerea was studied. The results indicated that the compound 8e-mediated defense response against B. cinerea was based on the accumulation of pathogenesis-related proteins and cell wall reinforcement by callose deposition. Quantitative analysis of salicylic acid (SA) and jasmonic acid (JA) and the increased expression of induced resistance-related genes and the defense-associated phenylalanine ammonia lyase revealed that the immune response triggered by compound 8e was highly associated with the SA signaling pathway. Significant upregulation of JA-related genes Cs-AOS2 indicated that the JA signaling pathway was also influenced. It was also shown that the plants treated with compound 8e promoted primary root elongation, which resulted in enhanced plant growth. Most importantly, these compounds have completely new structures compared with the traditional plant elicitors. Further research of 8e-mediated plant disease resistance might have a great influence on the development of plant elicitors.

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“…The key intermediates 3 and 4 were synthesized following the manner in our previous studies by the reaction of 1 (24 mmol, 6.53 g) and 2 (25 mmol, 5.15 g). − …”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 96%

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Design, Synthesis, and Fungicidal Activity of Novel Plant Elicitors Based on a Diversity-Oriented Synthesis Strategy

et al. 2022

J. Agric. Food Chem.

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Design, Synthesis, and Insecticidal Activities of Novel meta‐Diamide Compounds Containing Ethyl Acetate and Their Derivatives

Wang

Liu²,

Xiang³

et al. 2023

Chemistry & Biodiversity

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In this study, a series of meta-diamide compounds containing ethyl acetate group and their derivatives were designed and synthesized. Their insecticidal activities against Plutella xylostella, Spodoptera frugiperda and Alfalfa sprouts were evaluated. Preliminary bioassays showed that some of the title compounds exhibited excellent insecticidal activities. -6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-N-(4-cyanobenzoyl)glycinate and ethyl N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-N-(6-fluoronicotinoyl)glycinate showed 100 % mortality at 0.1 mg/L against Plutella xylostella and Spodoptera frugiperda, same to broflanilide. Their LC 50 against Plutella xylostella is 0.286 mg/L and 0.0218 mg/L, respectively. Moreover, compound ethyl N-(3-((2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-N-(6-fluoronicotinoyl)glycinate displayed faster control efficacy than broflanilide at 0.1 mg/L. The results indicated that meta-diamide compounds containing ethyl acetate group could be developed as novel and promising insecticides.

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Design, synthesis, antifungal activity and molecular docking of novel pyrazole‐4‐carboxamides containing tertiary alcohol and difluoromethyl moiety as potential succinate dehydrogenase inhibitors

Su,

Zhang,

et al. 2024

Pest Management Science

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BackgroundResistance problems with the long‐term and frequently use of existing fungicides, and lacking of structure diversity of traditional pyrazole‐4‐carboxamide succinate dehydrogenase inhibitors, it is highly required to design and develop new fungicides to address the resistance issue.ResultsDifferent from previous pyrazole‐4‐carboxamide succinate dehydrogenase inhibitors by breaking the norm of difluoromethyl at the C‐3 position of pyrazole and introducing a tertiary alcohol group at the C‐3 position, twenty‐seven novel pyrazole‐4‐carboxamide derivatives were designed, synthesized and characterized by 1H NMR, 13C NMR, 19F NMR and HR‐ESI‐MS. The crystal structures of compounds A14 and C5 were analyzed by single crystal X‐ray diffraction. Their in vitro antifungal activities were evaluated against phytopathogen Fusarium graminearum, Botrytis cinerea, Phytophthora capsica, Sclerotinia sclerotiorum, Thanatephorus cucumeris. The results displayed that most of them exhibited significant antifungal activities against S. sclerotiorum at 50 mg/L, the EC50 data of A8 and A14 were 3.96 and 2.52 mg/L, respectively. Their in vivo antifungal activities were evaluated against Pseudoperonospora cubensis, Puccinia sorghi schw, Colletotrichum gloeosporioides, F. graminearum, Erysiphe graminis, T. cucumeris, the control efficacies of A6, B3, C3, and C6 against E. graminis reached 100% at a concentration of 400 mg/L. The molecular docking results showed that the binding mode of the target compounds containing tertiary alcohols were similar to that of fluxapyroxad in SDH. In addition, tertiary alcohols were involved in the formation of hydrogen bonds.ConclusionThe excellent in vitro and in vivo inhibitory activities of novel pyrazole‐4‐carboxamide derivatives against SDH were reported for the first time, and they could be used as the potential lead compounds.This article is protected by copyright. All rights reserved.

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Synthesis and Fungicidal Activity of (E)-5-[1-(4-Phenyl-2-oxo-1-oxaspiro[4.5]dec-3-en-3-yl)ethylidene]-2-aminoimidazolin-4-one Derivatives

Cited by 6 publications

References 18 publications

Design, Synthesis, and Fungicidal Activity of Novel Plant Elicitors Based on a Diversity-Oriented Synthesis Strategy

Design, Synthesis, and Fungicidal Activity of Novel Plant Elicitors Based on a Diversity-Oriented Synthesis Strategy

Design, Synthesis, and Insecticidal Activities of Novel meta‐Diamide Compounds Containing Ethyl Acetate and Their Derivatives

Design, synthesis, antifungal activity and molecular docking of novel pyrazole‐4‐carboxamides containing tertiary alcohol and difluoromethyl moiety as potential succinate dehydrogenase inhibitors

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