Abstract:In
the current work, a series of 1-trifluoromethyl cinnamyl alcohol
derivatives were designed and synthesized and their antifungal activities
were evaluated. The bioassay result showed that most compounds exhibited
excellent antifungal activity in vitro at 10 μg
mL–1. Next, photostable and easily synthesized compound 2 with broad-spectrum antifungal activity in vitro was selected as a potential candidate to evaluate its antibacterial
and antifungal activities. The EC50 values of compound 2 against eight fungal… Show more
“…The following conclusions were drawn: a) Compared with other substituents, CF 3 -Ph-containing compounds 4t , 4u , and 4v exhibited the strongest anti-R. solani effect regardless of the specific positions of the −CF 3 group on the phenyl ring, having EC 50 values of 1.25, 1.22, and 0.50 μg/mL, respectively, which may be related to strong electronegativity, high lipophilicity, and high chemical stability of the CF 3 group; b). Combining the data from Tables and , the introduction of electron-donating groups (like CH 3 -, CH 3 O-, or (CH 3 ) 2 N-) into the phenyl ring was detrimental to the activity, except for the 4-OCH 3 -Ph-bearing compound 4g .…”
A total of 29 novel quinazoline-2-aminothiazole hybrids
containing
a 4-piperidinylamide linker were designed, synthesized, and evaluated
for their anti-microbial properties against phytopathogenic fungi
and bacteria of agricultural importance. The anti-fungal assays indicated
that some of the target compounds exhibited excellent inhibitory effects
in vitro against Rhizoctonia solani. For example, 11 compounds within this series (including 4a, 4g, 4h, 4j, 4o, 4s, 4t, 4u, 4v, 4y, and 4b′) were found to possess
EC50 values (effective concentration for 50% activity)
ranging from 0.42 to 2.05 μg/mL against this pathogen. In particular,
compound 4y with a 2-chloro-6-fluorophenyl substituent
displayed a potent anti-R. solani efficacy
with EC50 = 0.42 μg/mL, nearly threefold more effective
than the commercialized fungicide Chlorothalonil (EC50 =
1.20 μg/mL) and also slightly superior to the other fungicide
Carbendazim (EC50 = 0.53 μg/mL). Moreover, compound 4y could efficiently inhibit the growth of R. solani in vivo on the potted rice plants, displaying an impressive protection
efficacy of 82.3% at 200 μg/mL, better than those of the fungicides
Carbendazim (69.8%) and Chlorothalonil (48.9%). Finally, the mechanistic
studies showed that compound 4y exerted its anti-fungal
effects by altering the mycelial morphology, increasing the cell membrane
permeability, and destroying the cell membrane integrity. On the other
hand, some compounds demonstrated good anti-bacterial effects in vitro
against Xanthomonas oryzae pv. oryzae (Xoo). Overall, the presented results
implied that 4-piperidinylamide-bridged quinazoline-2-aminothiazole
hybrids held the promise of acting as lead compounds for developing
more efficient fungicides to control R. solani.
“…The following conclusions were drawn: a) Compared with other substituents, CF 3 -Ph-containing compounds 4t , 4u , and 4v exhibited the strongest anti-R. solani effect regardless of the specific positions of the −CF 3 group on the phenyl ring, having EC 50 values of 1.25, 1.22, and 0.50 μg/mL, respectively, which may be related to strong electronegativity, high lipophilicity, and high chemical stability of the CF 3 group; b). Combining the data from Tables and , the introduction of electron-donating groups (like CH 3 -, CH 3 O-, or (CH 3 ) 2 N-) into the phenyl ring was detrimental to the activity, except for the 4-OCH 3 -Ph-bearing compound 4g .…”
A total of 29 novel quinazoline-2-aminothiazole hybrids
containing
a 4-piperidinylamide linker were designed, synthesized, and evaluated
for their anti-microbial properties against phytopathogenic fungi
and bacteria of agricultural importance. The anti-fungal assays indicated
that some of the target compounds exhibited excellent inhibitory effects
in vitro against Rhizoctonia solani. For example, 11 compounds within this series (including 4a, 4g, 4h, 4j, 4o, 4s, 4t, 4u, 4v, 4y, and 4b′) were found to possess
EC50 values (effective concentration for 50% activity)
ranging from 0.42 to 2.05 μg/mL against this pathogen. In particular,
compound 4y with a 2-chloro-6-fluorophenyl substituent
displayed a potent anti-R. solani efficacy
with EC50 = 0.42 μg/mL, nearly threefold more effective
than the commercialized fungicide Chlorothalonil (EC50 =
1.20 μg/mL) and also slightly superior to the other fungicide
Carbendazim (EC50 = 0.53 μg/mL). Moreover, compound 4y could efficiently inhibit the growth of R. solani in vivo on the potted rice plants, displaying an impressive protection
efficacy of 82.3% at 200 μg/mL, better than those of the fungicides
Carbendazim (69.8%) and Chlorothalonil (48.9%). Finally, the mechanistic
studies showed that compound 4y exerted its anti-fungal
effects by altering the mycelial morphology, increasing the cell membrane
permeability, and destroying the cell membrane integrity. On the other
hand, some compounds demonstrated good anti-bacterial effects in vitro
against Xanthomonas oryzae pv. oryzae (Xoo). Overall, the presented results
implied that 4-piperidinylamide-bridged quinazoline-2-aminothiazole
hybrids held the promise of acting as lead compounds for developing
more efficient fungicides to control R. solani.
“…The incorporation of fluorine-containing groups into organic molecules is a potent strategy to improve their metabolic stability, lipophilicity, and membrane permeability. These enhancements make such molecules valuable in the development of human drugs and agrichemicals. , Trifluoromethylpyridine derivatives, in particular, have shown diverse biological activities, such as herbicidal, antifungal, and insecticidal activities. Consequently, they are frequently employed as active fragments in pesticide structures, with representative examples including the commercial fungicides fluopicolide and fluopimomide …”
In this study, a series of acrylamide derivatives containing
trifluoromethylpyridine
or piperazine fragments were rationally designed and synthesized.
Subsequently, the in vitro antifungal activities
of all of the synthesized compounds were evaluated. The findings revealed
that compounds 6b, 6c, and 7e exhibited >80% antifungal activity against Phomopsis sp. (Ps) at the concentration of 50 μg/mL.
Furthermore, the EC50 values for compounds 6b, 6c, and 7e against Ps were determined to be 4.49, 6.47, and 8.68 μg/mL, respectively,
which were better than the positive control with azoxystrobin (24.83
μg/mL). At the concentration of 200 μg/mL, the protective
activity of compound 6b against Ps reached
65%, which was comparable to that of azoxystrobin (60.9%). Comprehensive
mechanistic studies, including morphological studies with fluorescence
microscopy (FM), cytoplasmic leakage, and enzyme activity assays,
indicated that compound 6b disrupts cell membrane integrity
and induces the accumulation of defense enzyme activity, thereby inhibiting
mycelial growth. Therefore, compound 6b serves as a valuable
candidate for the development of novel fungicides for plant protection.
“…Rapid development and outbreak of plant diseases lead to tremendous output and economic loss to agricultural production per annum . A total of 120 million acres of area in China have been infected with bacterial diseases, which is the second largest bacterial disease outbreak of plants behind fungal infection. , For instance, bacterial blight of rice caused by Xanthomonas oryzae pv. Oryzae ( Xoo ) is thought to be one of the most deadly rice diseases in the entire world .…”
Plant bacterial illnesses are common and cause dramatic damage to agricultural goods all over the world, yet there are few efficient bactericides to alleviate them at present. To discover novel antibacterial agents, two series of quinazolinone derivatives with novel structures were synthesized and their bioactivity against plant bacteria was tested. Combining CoMFA model search and the antibacterial bioactivity assay, D32 was identified as a potent antibacterial inhibitor against Xanthomonas oryzae pv. Oryzae (Xoo), with an EC 50 value of 1.5 μg/mL, much better in inhibitory capacity compared to bismerthiazol (BT) and thiodiazole copper (TC) (31.9 and 74.2 μg/mL). The activities of compound D32 against rice bacterial leaf blight in vivo were 46.7% (protective activities) and 43.9% (curative activities), better than commercial drug thiodiazole copper (29.3% protective activities and 30.6% curative activities). Flow cytometry, proteomics, reactive oxygen species, and key defense enzymes were used to further investigate the relevant mechanisms of action of D32. The identification of D32 as an antibacterial inhibitor and revelation of its recognition mechanism not only open the possibility of developing new therapeutic strategies for treatment of Xoo but also provide clues for elucidation of the acting mechanism of quinazolinone derivative D32, which is a possible clinical candidate worth in-depth study.
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