Synthesis, S-alkylation, and fungicidal activity of 4-(benzylideneamino)thioglycolurils

Газиева, Галина А.; Nechaeva, Tatyana V.; Kostikova, N. N.; Sigay, Natalya V.; Серков, С. А.; Попков, С. В.

doi:10.1007/s11172-018-2180-x

Cited by 11 publications

(3 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Imidazole and benzimidazole cores are widely found in natural products and biologically active compounds [ 8 , 9 , 10 , 11 , 12 , 13 , 14 ]. 2-Thioderivatives of imidazole were found to possess antifungal activity [ 15 , 16 , 17 , 18 , 19 , 20 , 21 ]. 4-Methyl-2-methylthio-4-phenyl-1-phenylamino-1 H -imidazol-5(4 H )-one, known as the fungicide fenamidone , has been present on the market of agrochemical plant protection products since 2001.…”

Section: Introductionmentioning

confidence: 99%

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

Vinogradova

Alekseenko

Попков

et al. 2023

IJMS

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

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

Vinogradova

Alekseenko

Попков

et al. 2023

IJMS

View full text Add to dashboard Cite

show abstract

“…In the second step, bromine at para position is used for the Suzuki C–C coupling reaction, as shown in Scheme . It is also used as an intermediate in other N -alkylations, S -alkylations, and most importantly in C–C cross-coupling reactions. − …”

Section: Introductionmentioning

confidence: 99%

Continuous Synthesis and Separation of p-Bromobenzyl Bromide Using Atom-Efficient Bromination of p-Bromotoluene without Any Organic Effluent: Potential for Green Industrial Practice

Sancheti

Yadav

2021

Org. Process Res. Dev.

View full text Add to dashboard Cite

This work focuses on the bromination of p-bromotoluene (PBT) using different brominating agents such as liquid Br2, NaBr–NaBrO3, NaBr–NaBrO3–NaCl, NaBr–H2O2, and HBr–H2O2. NaBr–NaBrO3–NaCl is an eco-friendly brominating agent obtained from a bromine recovery plant. Both NaBr–NaBrO3 and NaBr–NaBrO3–NaCl were found to be nonhazardous and efficient brominating agents. Pure NaBr–NaBrO3 resulted in the best PBT conversion with 79.7% Br atom efficiency in water and 98.2% average Br atom efficiency using dichloroethane as a solvent. Dichloroethane is de facto no longer used in the US and Europe and is not eco-friendly; the process with water as a solvent is the best. The substrate to active bromine molar ratio of 3:1 was found to be sufficient to get the maximum selectivity of p-bromobenzyl bromide (PBBB). The low-temperature crystallization method was used for separation cum purification of the product. Unreacted PBT was recycled along with the dibromo byproduct obtained. The dibromo product, which was built up gradually in the reaction mixture over 10 successive batches, was converted back into PBBB/PBT through NaBH4 treatment of the mother liquor. This continuous process is highly sustainable and produces zero organic waste, making it potentially attractive toward green industrial implementation.

show abstract

“…2,6 More and more research has focused on semithioglycolurils I-IX (Figure 1), 2, including compounds I, II, V, VII, and VIII that were synthesized in our laboratory. 6,[12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] Although a wide range of trisubstituted semithioglycolurils I and II have been reported, they are still actively investigated, as some of them have antifungal and cytotoxic activities. 12,13 Other compounds III-IX are represented by several examples and used as scaffolds in the synthesis of semithiobambusurils (III and VII), 11,27 in Claisen condensation matrices (IV), 10 and in the synthesis of tri-, tetra-, and polycyclic systems (V) [28][29][30][31] and iminoglycolurils (V, VII, VIII).…”

mentioning

confidence: 99%

Synthesis and Structure of 1-Substituted Semithioglycolurils

et al. 2020

View full text Add to dashboard Cite

Two methods for the synthesis of previously unavailable 1-substituted semithioglycolurils were developed. These methods consist of the cyclocondensation of 1-substituted ureas with 4,5-dihydroxy- or 4,5-dimethoxyimidazolidine-2-thione or glyoxal, followed by the reaction of the resulting 1-substituted 4,5-dihydroxyimidazolidine-2-ones with HSCN in a two-step one-pot procedure. Two of the desired semithioglycolurils were obtained as conglomerates.

show abstract

Synthesis, S-alkylation, and fungicidal activity of 4-(benzylideneamino)thioglycolurils

Cited by 11 publications

References 20 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

Continuous Synthesis and Separation of p-Bromobenzyl Bromide Using Atom-Efficient Bromination of p-Bromotoluene without Any Organic Effluent: Potential for Green Industrial Practice

Synthesis and Structure of 1-Substituted Semithioglycolurils

Contact Info

Product

Resources

About