The Synthesis and Fungicidal Activity of 2-Substituted 1-Azol-1-ylmethyl-6-arylidenecyclohexanols

Попков, С. В.; Kovalenko, L. V.; Bobylev, Mikhail M.; Molchanov, O. Yu.; Krimer, M. Z.; Tashchi, V. P.; Putsykin, Yury G.

doi:10.1002/(sici)1096-9063(199702)49:2<125::aid-ps506>3.0.co;2-0

Cited by 22 publications

(6 citation statements)

References 4 publications

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“…Synthesized alkylthio derivatives 4–6 were tested in vitro to a common conventional procedure [ 20 , 23 , 24 , 25 , 26 ] with six phytopathogenic fungi characterized by high impact on crop production: Venturia inaequalis , Rhizoctonia solani , Fusarium oxysporum , Fusarium moniliforme , Bipolaris sorokiniana , and Sclerotinia sclerotiorum . The effect of the testing compounds on the mycelium radial growth in potato-saccharose agar was measured at a concentration 30 μg mL −1 .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Evaluation on the Fungicidal Activity of S-Alkyl Substituted Thioglycolurils

Vinogradova

Alekseenko

Попков

et al. 2023

IJMS

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A series of S-alkyl substituted thioglycolurils was prepared through the alkylation of corresponding thioglycolurils with halogenoalkanes and tested for their fungicidal activity against six phytopathogenic fungi from different taxonomic classes: Venturia inaequalis, Rhizoctonia solani, Fusarium oxysporum, Fusarium moniliforme, Bipolaris sorokiniana, and Sclerotinia sclerotiorum, and two pathogenic yeasts: Candida albicans and Cryptococcus neoformans var. grubii. A number of S-alkyl substituted thioglycolurils exhibited high activity against Venturia inaequalis and Rhizoctonia solani (85–100% mycelium growth inhibition), and moderate activity against other phytopathogens. S-Ethyl substituted thioglycolurils possessed a high activity against Candida albicans. Additionally, the hemolytic and cytotoxic properties of promising derivatives were determined using human red blood cells and human embryonic kidney cells, respectively. Two S-ethyl derivatives possessed both low cytotoxicity against normal human cells and high fungicidal activity against Candida albicans.

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Section: Resultsmentioning

confidence: 99%

“…The fungicidal activities were tested according to the conventional procedure [ 20 , 23 , 24 , 25 , 26 ] with six phytopathogenic fungi from different taxonomic classes: Venturia inaequalis ( V. i. ), Rhizoctonia solani ( R. s. ), Fusarium oxysporum ( F. o.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Evaluation on the Fungicidal Activity of S-Alkyl Substituted Thioglycolurils

Vinogradova

Alekseenko

Попков

et al. 2023

IJMS

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“…Fungicidal activity tests were performed according to a standard procedure − against six phytopathogenic fungi from different taxonomic classes: V.i. - Venturia inaequalis MRA-16-2, R.s.…”

Section: Methodsmentioning

confidence: 99%

4-Nitropyrazolin-5-ones as Readily Available Fungicides of the Novel Structural Type for Crop Protection: Atom-Efficient Scalable Synthesis and Key Structural Features Responsible for Activity

Budnikov

Lopat’eva

Krylov

et al. 2022

J. Agric. Food Chem.

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The development of new types of fungicides for agriculture and medicine is highly desirable due to the uprising fungal resistance against commonly used compounds. Herein, 4-substituted-4-nitropyrazolin-5-ones (nitropyrazolones) were proposed as highly active fungicides of the novel structural type. The first scalable and practical method for the nitropyrazolone synthesis was proposed, which is atom-efficient, is applicable for the multigram scale synthesis, and allows for production of a wide variety of nitropyrazolones with high yields and purity. The synthesized compounds demonstrated high fungicidal activity against the broad spectrum of phytopathogenic fungi (Venturia inaequalis, Rhizoctonia solani, Fusarium oxysporum, Fusarium moniliforme, Bipolaris sorokiniana, and Sclerotinia sclerotiorum). Their mycelium growth inhibiting activity was comparable or superior to that of kresoximmethyl. In vitro activity against Staphyloccocus aureus, Candida albicans, and Aspergillus niger revealed that nitropyrazolones are promising candidates against human pathogens. The key factors for the manifestation of high fungicidal activity were established to be an aromatic substituent on the N1 atom and small substituents, such as methyl, at the C3 and C4 positions of the pyrazolone ring.

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“…The fungicidal activity was investigated according to a standard procedure [63][64][65][66][67][68][69]. The strains for fungicidal studies were obtained from the working collection of the All-Russian Research Institute for Phytopathology (B. Vyazemy, Moscow reg., Russia): Venturia inaequalis (V.i.)…”

Section: Investigation Of Fungicidal Activity (Table 1)mentioning

confidence: 99%

4-Disubstituted Pyrazolin-3-Ones—Novel Class of Fungicides against Phytopathogenic Fungi

et al. 2023

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The search for fungicides of novel classes is the long-standing priority in crop protection due to the continuous development of fungal resistance against currently used types of active compounds. Recently, 4-nitropyrazolin-3-ones were discovered as highly potent fungicides, of which activity was believed to be strongly associated with the presence of a nitro group in the pyrazolone ring. In this paper, a series of 4-substituted pyrazolin-3-ones were synthesized and their fungicidal activity against an important species of phytopathogenic fungi (Venturia inaequalis, Rhizoctonia solani, Fusarium oxysporum, Fusarium moniliforme, Bipolaris sorokiniana, and Sclerotinia sclerotiorum) was tested in vitro. We discovered that 4-mono and 4,4-dihalogenated pyrazolin-3-ones demonstrate fungicidal activity comparable to that of 4-nitropyrazolin-3-ones and other modern fungicides (such as kresoxim methyl). This discovery indicates that NO2 moiety can be replaced by other groups of comparable size and electronic properties without the loss of fungicidal activity and significantly expands the scope of potent new fungicides based on a pyrazolin-3-one fragment.

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The Synthesis and Fungicidal Activity of 2-Substituted 1-Azol-1-ylmethyl-6-arylidenecyclohexanols

Cited by 22 publications

References 4 publications

Synthesis and Evaluation on the Fungicidal Activity of S-Alkyl Substituted Thioglycolurils

Synthesis and Evaluation on the Fungicidal Activity of S-Alkyl Substituted Thioglycolurils

4-Nitropyrazolin-5-ones as Readily Available Fungicides of the Novel Structural Type for Crop Protection: Atom-Efficient Scalable Synthesis and Key Structural Features Responsible for Activity

4-Disubstituted Pyrazolin-3-Ones—Novel Class of Fungicides against Phytopathogenic Fungi

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