Synthesis and antifungal activity of novel pyrazolecarboxamide derivatives containing a hydrazone moiety

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BackgroundPant diseases in agriculture are extremely difficult to control, which bring about for billions of dollars in economic losses worldwide each year; Nicotinamide derivatives has attracted more and more attention in the field of pesticide due to their broad bioactivities. In an effort to discover new molecules with good antifungal activity, a series of nicotinamide derivatives containing 1,3,4-oxadiazole were synthesized and bio-assayed.ResultsBioassays demonstrated that some of the title compounds exhibited favorable antifungal activities against Gibberella zeae, Fusarium oxysporum, and Cytospora mandshurica. compounds 7b, 7c, 8, 9a, 9b, and 9c displayed 46.4%, 39.6%, 53.0%, 43.2%, 58.3%, 45.6% activities against G. Zeae, respectively; the activities of compounds 7a, 7b, 8, 9a, 9b, and 9c against F. oxysporum were 55.2%, 51.1%, 58.9%, 63.2%, 53.3%, and 47.6%, respectively; whereas inhibitory rates of compounds 7a, 7b, 7c, 8, 9a, 9b, and 9c on C. mandshurica were 53.1%, 49.9%, 44.9%, 52.8%, 59.8%, 54.5%, and 49.3%, respectively.ConclusionA series of the novel nicotinamide derivatives containing 1,3,4-oxadiazole were synthesized and bio-assayed. The results of antifungal tests revealed that the synthesized nicotinamide derivatives possessed weakly to moderately antifungal activities against G. zeae, F. oxysporum, and C. mandshurica. Most of the synthesized compounds exhibited similar activities as (or higher than) these of hymexozol on their corresponding fungus, and compounds 7a, 8, 9a, and 9b showed considerable prospects for further optimization. Primary structure-activity relationships revealed that the introduction of the groups of 4-chloro-6-methyl on benzene, the hydrazone group containing N,N-dimethylamino, and acetyl at -NH2 could enhance the antifungal activity.

Section: Resultsmentioning

confidence: 99%

Synthesis and antifungal activities of novel nicotinamide derivatives containing 1,3,4-oxadiazole

Kang

Luo

et al. 2013

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“…Mepronil, flutolanil, and tiadinil are known for their ability to protect certain plants from severe diseases and pests (Figure 1). In our recent publications [15,16], several pyrazole amide derivatives containing a hydrazone moiety have been synthesized and tested for their antifungal activity. The synthesized compounds exhibited antifungal activity against Fusarium oxysporum and Cytospora mandshurica , with inhibitory rates ranging from 40.82% to 50.32%.…”

Section: Introductionmentioning

confidence: 99%

“…The synthesized compounds exhibited antifungal activity against Fusarium oxysporum and Cytospora mandshurica , with inhibitory rates ranging from 40.82% to 50.32%. In addition, some hydrazone derivatives containing a pyridine moiety possessed high antibacterial activity against Ralstonia Solanacearum [16]. 1-(2,4-Dichlorophenyl)-3-aryl-2-(1 H -1,2,4-triazol-1-yl) prop-2-en-1-one derivatives have been synthesized using aldol condensation between 1-(2,4-dichlorophenyl)-2-(1 H -1,2,4-triazol-1-yl) ethan one and an aryl aldehyde.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety

Tang

Jin

Mou

et al. 2013

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BackgroundPlant fungi (e.g., Pellicularia sasakii, Gibberella zeae, Fusarium oxysporum, and Cytospora mandshurica and Phytophthora infestans) and bacteria (e.g., Ralstonia solanacearum) are extremely difficult to manage in agricultural production. The high incidence of plant mortality and the lack of effective control methods make P. sasakii and R. solanacearum two of the world’s most destructive plant pathogens. Pathogenic fungi and bacteria are responsible for billions of dollars in economic losses worldwide each year. Thus, we designed an active amide structure and synthesized a series of novel amide derivatives containing a triazole moiety to discover new bioactive molecules and pesticides that can act against fungi and bacteria.ResultsA series of amide derivatives containing a triazole moiety were synthesized. All the obtained compounds were characterized through proton and carbon nuclear magnetic resonance spectroscopy, infrared spectroscopy, and elemental analysis. Preliminary antifungal activity test showed that some of the synthesized compounds exhibited moderate antifungal activity against P. sasakii, G. azeae, F. oxysporum, C. mandshurica, and P. infestans at 50 mg/L. Compound 4u displayed more potent antifungal activity against P. sasakii and G. azeae than hymexazol. Preliminary antibacterial activity results showed that some of the synthesized compounds exhibited high anti-bacterial activity against R. solanacearum at 200 mg/L. Compounds 4m and 4q displayed high antibacterial activity against R. solanacearum, with 71% and 65% inhibitory rates, respectively.ConclusionsA series of novel amide derivatives containing 1,2,4-triazole moiety were synthesized through the reaction of intermediate 3 with different acyl chlorides and anhydrous potassium carbonates in anhydrous tetrahydrofuran at 50°C, using 2,4-dichloroacetophenoneas as a starting material. The title compounds exhibited high inhibitory effects against P. sasakii, R. solanacearum, and G. azeae.

“…Amide derivatives have become one of the focuses in the development of pesticides because of their high biological activities, such as fungicidal activities [8-11], herbicidal activities [12-15], insecticidal activities [16,17], anticancer activity [18,19], antibacterial activity [20] and so on. In line with our continueous efforts to synthesize bioactive lead compounds, the title compounds were designed by introducing amide pharmacophore into the valine scaffold.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and larvicidal activity of novel diamide derivatives against Culex pipiens

Zhu

et al. 2012

BackgroundCulex is an important mosquito as vectors for the transmission of serious diseases, such as filariasis, West Nile virus, dengue, yellow fever, chikungunya and other encephalitides. Nearly one billion people in the developing countries are at risk. In order to discover new bioactive molecules and pesticides acting on mosquito, we designed active amide structure and synthesized a series of novel diamide derivatives.ResultsA series of novel diamide derivatives were designed and synthesized. Their structures were characterized by 1 H NMR, FTIR and HRMS. The single crystal structure of compound 6n was determined to further elucidate the structure. Biological activities of these compounds were tested. Most of them exhibited higher mosquito larvicidal activity. Especially compound 6r displayed relatively good activity to reach 70% at 2 μg/mL.ConclusionA practical synthetic route to amide derivatives by the reaction of amide with another acid is presented. This study suggests that the diamide derivatives exhibited good effective against mosquito.