Structural Modification of Saccharin Containing 2‐Aminothiazole As Potential Fungicidal Agents

Zhang, Tianyuan; You, Shuyan; Zheng, Suiping; Huang, Danling; Cheng, Yong‐Xian

doi:10.1002/slct.202103603

Cited by 4 publications

(3 citation statements)

References 24 publications

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“…The fungicidal activities of the above compounds to A. alternala, S. sclerotiorum, B. cinerea, and F. oxysporum were tested by the method described in our previous report. [22][23] Briefly, 0.5 cm mycelial plugs of the pathogens were prepared and transferred onto PDA plates supplemented with the indicated concentrations of the compounds. The same volumes of DMSO were used as a control.…”

Section: Bioactivity Assaymentioning

confidence: 99%

Structural Optimization, Fungicidal Activities Evaluation, DFT Study and Structure‐Activity Relationship of Dopamine Derivatives with Benzothiazole Fragment from Polyrhachis dives

Wang

Huang

Cheng

2023

Chemistry & Biodiversity

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In our previous work, two dopamine derivatives with benzothiazole fragment were isolated and identified from Polyrhachis dives (P. dives). Based on their characteristic structure, we used them as lead compound to carry out structural optimization and subsequent fungicidal evaluation. Here 20 dopamine derivatives with benzothiazole fragment were designed and synthesized by a facile method, and their structures were characterized by 1 H-NMR, 13 CNMR and HMRS. In bioassays, most of the title compounds possess potential fungicidal activities against Altenaia alternala (A. alternala) and Botrytis cinerea (B. cinerea). Especially, (E)-N-(2-(benzo[d]thiazol-6-yl)ethyl)-3-(ptolyl)acrylamide and (E)-N-(2-(benzo[d]thiazol-6-yl)ethyl)-3-(4-(trifluoromethyl)phenyl)acrylamide displayed 29.3 mg/L and 10.7 mg/L EC 50 value against A. alternala, respectively, which possessed equivalent fungicidal activities level to hymexazol.

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Section: Bioactivity Assaymentioning

confidence: 99%

Structural Optimization, Fungicidal Activities Evaluation, DFT Study and Structure‐Activity Relationship of Dopamine Derivatives with Benzothiazole Fragment from Polyrhachis dives

Wang

Huang

Cheng

2023

Chemistry & Biodiversity

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“…16 Compared with five-membered heterocycles like oxazole and imidazole, the thiazole ring has unique features owing to the presence of low-lying C S ⊞* orbitals, which lead to small regions of low electron density at the sulfur atom and thus is an important part of drug-target interactions. 17 Among the various thiazole derivatives, the 2-aminothiazole core is of particular significance in the field of heterocyclic chemistry and is a privileged structural motif for lead discovery and drug design, showing multifarious bioactivities such as antibacterial, 18,19 antifungal, 20 insecticidal, 21 anticancer, 22 antiviral, 23 and anti-inflammatory properties. 24 Some commercialized drugs/pesticides based on this core include the antibiotic abafungin (Fig.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and antimicrobial evaluation of 2‐aminothiazole derivatives bearing the 4‐aminoquinazoline moiety against plant pathogenic bacteria and fungi

Wan,

Yang,

Tian

et al. 2023

Pest Management Science

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BACKGROUNDTo find more effective agricultural antibiotics, a class of new 2‐aminothiazole derivatives containing the 4‐aminoquinazoline moiety were synthesized and evaluated for their antimicrobial properties against phytopathogenic bacteria and fungi of agricultural importance.RESULTSAll the target compounds were fully characterized by 1H NMR, 13C NMR, and high‐resolution mass spectrometry. The bioassay results showed that compound F29 with a 2‐pyridinyl substituent exhibited an outstanding antibacterial effect against Xanthomonas oryzae pv. oryzicola (Xoc) in vitro, having an half‐maximal effective concentration (EC50) value as low as 2.0 μg/mL (over 30‐fold more effective than the commercialized agrobactericide bismerthiazol, with an EC50 value of 64.3 μg/mL). In addition, compound F8 with a 2‐fluorophenyl group demonstrated a good inhibitory activity toward the bacterium Xanthomonas axonopodis pv. citri (Xac), around twofold more active than bismerthiazol in terms of their EC50 values (22.8 versus 71.5 μg/mL). Interestingly, this compound also demonstrated a notable fungicidal effect against Phytophthora parasitica var. nicotianae, with an EC50 value largely comparable with that of the commercialized fungicide carbendazim. Finally, mechanistic studies revealed that compound F29 exerted its antibacterial effects by increasing the permeability of bacterial membranes, reducing the release of extracellular polysaccharides, and triggering morphological changes of bacterial cells.CONCLUSIONCompound F29 has promising potential as a lead compound for developing more efficient bactericides to fight against Xoc. © 2023 Society of Chemical Industry.

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“…Oomycetes are one of the important pathogens that cause many crop diseases [1–3] . Oomycetes have a wide variety that are harmful after infection.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Fungicidal Activities of Benzofuran‐Substitutes Cinnamamide Compounds

et al. 2023

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The commercially available dimethomorph is a mixture of two isomers, among which Z‐ dimethomorph has an excellent control effect against oomycetes, while E‐dimethomorph has less fungicidal activity. Therefore, in this paper, a series of novel benzofuran‐modified cinnamamide derivatives were designed and synthesized by “fixing” the cis‐styrene group in Z‐dimethomorph with benzofuran group. And the modification of the molecular structure of cinnamamide compounds could be beneficial to improve its practical application performance. The synthesized products were evaluated for their antifungal activity against 7 strains of phytopathogenic fungi. It was found that the antifungal spectrum and fungicidal activities of some compounds were improved compared with the commercial fungicides dimethomorph and flumorph. Furthermore, for benzofuran‐modified cinnamamide derivatives, substituted bis‐methoxy in the phenyl ring of cinnamate is crucial to inhibit Phytophthora infestans and Phytophthora dreschsleri.

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Structural Modification of Saccharin Containing 2‐Aminothiazole As Potential Fungicidal Agents

Cited by 4 publications

References 24 publications

Structural Optimization, Fungicidal Activities Evaluation, DFT Study and Structure‐Activity Relationship of Dopamine Derivatives with Benzothiazole Fragment from Polyrhachis dives

Structural Optimization, Fungicidal Activities Evaluation, DFT Study and Structure‐Activity Relationship of Dopamine Derivatives with Benzothiazole Fragment from Polyrhachis dives

Design, synthesis, and antimicrobial evaluation of 2‐aminothiazole derivatives bearing the 4‐aminoquinazoline moiety against plant pathogenic bacteria and fungi

Synthesis and Fungicidal Activities of Benzofuran‐Substitutes Cinnamamide Compounds

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