Design, synthesis, fungicidal property and QSAR studies of novel <i>β</i>‐carbolines containing urea, benzoylthiourea and benzoylurea for the control of rice sheath blight

Zhang, Zhijun; Zeng, Yong; Jiang, Zongyong; Shu, Benshui; Veeran, Sethuraman; Zhong, Guohua

doi:10.1002/ps.4873

Cited by 55 publications

(36 citation statements)

References 35 publications

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“…On the other hand, urea structure also is an important skeleton in bioactive molecules. The urea derivatives also exhibited diverse bioactivities, such as mosquito activity , antimicrobial activity , antiviral activity , antifungal activity , antinociceptive activity , and anticancer activity .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, Antifungal Activity, and Docking Study of Difluoromethyl Pyrazole Derivatives

Zhai

Cai

et al. 2019

Journal of Heterocyclic Chem

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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 better than control. It is possible that difluoromethylpyrazole acyl urea derivatives can be a leading compound for the development of new fungicides against the two fungi with further structure optimization. Furthermore, docking model was studied to establish structure–activity relationship of difluoromethylpyrazole acyl urea derivatives.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, Antifungal Activity, and Docking Study of Difluoromethyl Pyrazole Derivatives

Zhai

Cai

et al. 2019

Journal of Heterocyclic Chem

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“…Of these compounds, indole (7, EC 50 = 25.56 µg/mL) displayed superior fungicidal activity, and was 7-fold as potent as validamycin A (EC 50 = 183.00 µg/mL). Additionally, it can be seen quite clearly that the structural changes in general were detrimental to activity and no favorable substitution could be found for the 2-or 3-position, even after extensive probing with a variety of diverse groups (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26). These findings implied that indole was a potent fungicidal template for further modification and derivatization.…”

Section: Chemistrymentioning

confidence: 99%

“…The fungi R. solani GD-118 was provided by our laboratory, and the rice cultivar (Xiangyazhan) was planted according to our previously reported method [15]. The in vitro and in vivo fungicidal activity against R. solani were tested following our previously reported method [17].…”

Section: In Vitro and In Vivo Fungicidal Activity Against R Solanimentioning

confidence: 99%

“…For instant, the representative harmala alkaloids harmine (Figure 1, 1), harmaline (2) and tetrahydroharmine (3) displayed marginal and similar fungicidal activity against R. solani [13]. In our previous work, we had introduced urea [15] and oxadiazole [16] groups into the 3 position of β-carboline scaffold and obtained two potent compounds 5 and 6 with respective EC50 values of 69.52 and 4.24 μg/mL against R. solani. Continued exploration of the β-carboline through optimization of the ring C of β-carboline led to 1,2,4,9-tetrahydro-3-thia-9-aza-fluorene derivatives with greater fungicidal efficacy giving rise to a highly effective agent 4 (EC50 = 2.35 μg/mL) [17], which indicated that the ring C of β-carboline was attractive for further simplifications.…”

Section: Introductionmentioning

confidence: 98%

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Simplification of Natural β-Carboline Alkaloids to Obtain Indole Derivatives as Potent Fungicides against Rice Sheath Blight

et al. 2020

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The increasing resistance of rice sheath blight caused by Rhizoctonia solani highlights the need for highly effective and environmentally benign agents. Natural β-carboline alkaloids were simplified to obtain a series of indole derivatives, and their fungicidal activity and preliminary mode of action against R. solani were also evaluated. The initial hit indole (7) displayed significant fungicidal activity with an EC50 value of 25.56 μg/mL, and was selected for further optimization. Importantly, compound 55, the most active compound, had an EC50 value of 0.62 μg/mL, and approximately 300-fold more potent than validamycin A (EC50 = 183.00 μg/mL). In vivo bioassay also demonstrated that compound 55 showed better fungicidal activities than validamycin A. Moreover, the mechanism studies revealed that compound 55 not only caused remarkable morphological and structural alterations of R. solani hyphae, but also induced the loss of mitochondrial membrane potential and interfered with DNA synthesis. Therefore, compound 55 showed superior fungicidal activity against R. solani, and the elucidated mode of action supported the potential application of compound 55 against rice sheath blight.

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“…Thiourea molecules are of interest in themselves and as ligands for metal ions (Saeed et al, 2014). The free molecules, including benzoyl derivatives, are well-known to exhibit various biological properties, for example, anti-bacterial, antifungal and anti-viral activities as well as cytotoxicity (Hallur et al, 2006;Cunha et al, 2007;Saeed et al, 2010;Gunasekaran et al, 2017;Zhang et al, 2018;. The combination of hard (oxygen) and soft (sulfur) donor atoms along with nitrogen suggests that benzoylthioureas can function as versatile ligands to metals.…”

Section: Chemical Contextmentioning

confidence: 99%

3,3-Bis(2-hydroxyethyl)-1-(4-methylbenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study

Tan

Azizan

Jotani³

et al. 2019

Acta Cryst E

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In the title tri-substituted thiourea derivative, C13H18N2O3S, the thione-S and carbonyl-O atoms lie, to a first approximation, to the same side of the molecule [the S—C—N—C torsion angle is −49.3 (2)°]. The CN2S plane is almost planar (r.m.s. deviation = 0.018 Å) with the hydroxyethyl groups lying to either side of this plane. One hydroxyethyl group is orientated towards the thioamide functionality enabling the formation of an intramolecular N—H...O hydrogen bond leading to an S(7) loop. The dihedral angle [72.12 (9)°] between the planes through the CN2S atoms and the 4-tolyl ring indicates the molecule is twisted. The experimental molecular structure is close to the gas-phase, geometry-optimized structure calculated by DFT methods. In the molecular packing, hydroxyl-O—H...O(hydroxyl) and hydroxyl-O—H...S(thione) hydrogen bonds lead to the formation of a supramolecular layer in the ab plane; no directional interactions are found between layers. The influence of the specified supramolecular interactions is apparent in the calculated Hirshfeld surfaces and these are shown to be attractive in non-covalent interaction plots; the interaction energies point to the important stabilization provided by directional O—H...O hydrogen bonds.

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Design, synthesis, fungicidal property and QSAR studies of novel β‐carbolines containing urea, benzoylthiourea and benzoylurea for the control of rice sheath blight

Cited by 55 publications

References 35 publications

Synthesis, Crystal Structure, Antifungal Activity, and Docking Study of Difluoromethyl Pyrazole Derivatives

Synthesis, Crystal Structure, Antifungal Activity, and Docking Study of Difluoromethyl Pyrazole Derivatives

Simplification of Natural β-Carboline Alkaloids to Obtain Indole Derivatives as Potent Fungicides against Rice Sheath Blight

3,3-Bis(2-hydroxyethyl)-1-(4-methylbenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study

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