Abstract:Nine novel difluoromethylpyrazole acyl urea derivatives were synthesized via seven steps conveniently. All the structures were determined by 1H‐NMR, 13C‐NMR, HRMS, and X‐ray diffraction. The in vivo fungicidal activities were determined against Corynespora mazei, Botrytis cinerea, Fusarium oxysporum, and Pseudomonas syringae, respectively. The bioassay results indicated that some of them displayed good control effective (around 50 and 80%) against P. syringae and B. cinerea at 50 mg/L, respectively, which is b… Show more
“…Recently, it has been shown that the antifungal activity of a variety of compounds is mainly due to inhibition of succinate dehydrogenase (SDH) which is a component of the mitochondrial respiratory chain and the tricarboxylic acid cycle [21][22][23]. Thus, the interactions of antifungal compounds with the ubiquinone binding site have been evaluated to understand the experimental activity shown by different series of related compounds [24][25][26][27][28]. In this work, we have performed molecular docking studies of geranylated phenols carrying one (23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33), two (34)(35)(36)(37)(38) or no (14, 18, 19) hydroxyl groups in the side alkyl chain.…”
Section: Molecular Docking Studymentioning
confidence: 99%
“…Thus, the interactions of antifungal compounds with the ubiquinone binding site have been evaluated to understand the experimental activity shown by different series of related compounds [24][25][26][27][28]. In this work, we have performed molecular docking studies of geranylated phenols carrying one (23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33), two (34)(35)(36)(37)(38) or no (14, 18, 19) hydroxyl groups in the side alkyl chain. Molecular coupling of these compounds to a single crystal structure of SDH (PDB code 2FBW) was carried out by using Glide software.…”
“…Binding energies, obtained from molecular docking studies and antifungal activities against B. cinerea (EC 50 values) of geranylated phenols with one(14,(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33), two(34)(35)(36)(37)(38) or none(18,19,21) hydroxyl groups in the side alkyl chain. CBE is used for comparison 1 .…”
Botrytis cinerea is a ubiquitous fungus that affects hundreds of plants, resulting in economic losses to the horticulture and fruit industry. The search for new antifungal agents is a matter of current interest. Thus, in this work a series of geranylated phenols in which the side alkyl chain has been hydrated have been synthesized, and their activity against B. cinerea has been evaluated. The coupling of phenol and geraniol has been accomplished under microwave irradiation obtaining the highest reaction yields in the shortest reaction times. Hydration of the side chain was carried out in dioxane with p-toluenesulfonic acid polymer-bound as the catalyst. All synthesized compounds were tested against B. cinerea using the growth inhibition assay and EC50 values were determined. The results show that activity depends on the number and nature of functional groups in the phenol ring and hydration degree of the geranyl chain. The most active compound is 1,4-dihydroquinone with one hydroxyl group attached at the end of the alkyl chain. Results from a molecular docking study suggest that hydroxyl groups in the phenol ring and alkyl chain are important in the binding of compounds to the active site, and that the experimental antifungal activity correlates with the number of H-bond that can be formed in the binding site.
“…Recently, it has been shown that the antifungal activity of a variety of compounds is mainly due to inhibition of succinate dehydrogenase (SDH) which is a component of the mitochondrial respiratory chain and the tricarboxylic acid cycle [21][22][23]. Thus, the interactions of antifungal compounds with the ubiquinone binding site have been evaluated to understand the experimental activity shown by different series of related compounds [24][25][26][27][28]. In this work, we have performed molecular docking studies of geranylated phenols carrying one (23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33), two (34)(35)(36)(37)(38) or no (14, 18, 19) hydroxyl groups in the side alkyl chain.…”
Section: Molecular Docking Studymentioning
confidence: 99%
“…Thus, the interactions of antifungal compounds with the ubiquinone binding site have been evaluated to understand the experimental activity shown by different series of related compounds [24][25][26][27][28]. In this work, we have performed molecular docking studies of geranylated phenols carrying one (23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33), two (34)(35)(36)(37)(38) or no (14, 18, 19) hydroxyl groups in the side alkyl chain. Molecular coupling of these compounds to a single crystal structure of SDH (PDB code 2FBW) was carried out by using Glide software.…”
“…Binding energies, obtained from molecular docking studies and antifungal activities against B. cinerea (EC 50 values) of geranylated phenols with one(14,(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33), two(34)(35)(36)(37)(38) or none(18,19,21) hydroxyl groups in the side alkyl chain. CBE is used for comparison 1 .…”
Botrytis cinerea is a ubiquitous fungus that affects hundreds of plants, resulting in economic losses to the horticulture and fruit industry. The search for new antifungal agents is a matter of current interest. Thus, in this work a series of geranylated phenols in which the side alkyl chain has been hydrated have been synthesized, and their activity against B. cinerea has been evaluated. The coupling of phenol and geraniol has been accomplished under microwave irradiation obtaining the highest reaction yields in the shortest reaction times. Hydration of the side chain was carried out in dioxane with p-toluenesulfonic acid polymer-bound as the catalyst. All synthesized compounds were tested against B. cinerea using the growth inhibition assay and EC50 values were determined. The results show that activity depends on the number and nature of functional groups in the phenol ring and hydration degree of the geranyl chain. The most active compound is 1,4-dihydroquinone with one hydroxyl group attached at the end of the alkyl chain. Results from a molecular docking study suggest that hydroxyl groups in the phenol ring and alkyl chain are important in the binding of compounds to the active site, and that the experimental antifungal activity correlates with the number of H-bond that can be formed in the binding site.
“…Many studies 6,21,22 on HPPD inhibitors have proven that prodrug-type HPPD herbicides are an effective method of obtaining new HPPD inhibitors, such as the commercial HPPD herbicides benzobicyclon, isoxaflutole, benzofenap, pyrazolynate and pyrazoxyfen. As a part of our job in designing and synthesizing novel pyrazole derivatives with pesticidal activity, [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41] the pyrazole HPPD herbicides were used as lead compound, the 3-position of benzene ring was replaced by a flexible chain, and the hydroxyl group of pyrazole ring was also etherified or esterified. Through the prodrug strategy, we hoped that better herbicidal activity would result.…”
Difluoroacetohydrazonoyl bromides, which are stable in air at room temperature, are demonstrated to be good difluoromethyl building blocks for construction of CF2H‐substituted pyrazoline and pyrazole compounds via [3+2] cycloaddition with electron‐deficient olefins under mild conditions. A series of CF2H‐substituted pyrazolines and pyrazoles were obtained in good yields. The method has the advantages of mild reaction conditions, good regioselectivity, broad substrate scopes and easy operation.
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