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

Wu J, Wang J, Hu D, He M, Jin L, Song B - Chem Cent J (2012)

Bottom Line: Their structures were characterized by 1 H-NMR, 13 C-NMR, IR, and elemental analysis.The activity of compounds 7a, 7f, 7g, 7h, 7i, 7j, 7l and 7q were 40.82%, 47.78%, 50.32%, 40.82%, 49.05%, 48.73%, 40.19% and 45.89%, respectively, and the synthesized compounds showed certain antifungal activities against F. oxysporum and C.mandshurica.A practical synthetic route to pyrazole amide derivatives containing a hydrazone moiety were synthesized by the condensation of intermediates 5-chloro-N-(4-subsititued-2-(hydrazinecarbonyl)-6-methylphenyl)-1,3-dimethyl-1 H-pyrazole-4-carboxamide with different aldehydes or ketones in ethanol at room temperature is presented, the results of the study suggested that the pyrazole amide derivatives containing hydrazone moieties could inhibit the growth of G. zeae, F. oxysporium and C. mandshurica to a certain extent.

View Article: PubMed Central - HTML - PubMed

Affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, China. basong@gzu.edu.cn.

ABSTRACT

Background: The plant pathogenic fungus (such as Gibberella zeae, Fusarium oxysporum and Cytospora mandshurica) causes devastating disease in agriculture. The pathogenic fungus is responsible for billions of dollars in economic losses worldwide each year. In order to discover new fungicidal molecule with good fungicidal activity against G. zeae, F. oxysporum, and C. mandshurica, we sought to combine the active sub-structure of hydrazone and pyrazole amide derivatives together to design and synthesize novel pyrazole amide derivatives containing a hydrazone moiety.

Results: A series of novel pyrazole amide derivatives bearing hydrazone moiety were synthesized. Their structures were characterized by 1 H-NMR, 13 C-NMR, IR, and elemental analysis. The preliminary biological assays revealed that most of the synthesized compounds exhibit favorable antifungal activities against G. zeae. The activity of compounds 7a, 7f, 7g, 7h, 7i, 7j, 7l and 7q were 40.82%, 47.78%, 50.32%, 40.82%, 49.05%, 48.73%, 40.19% and 45.89%, respectively, and the synthesized compounds showed certain antifungal activities against F. oxysporum and C.mandshurica.

Conclusion: A practical synthetic route to pyrazole amide derivatives containing a hydrazone moiety were synthesized by the condensation of intermediates 5-chloro-N-(4-subsititued-2-(hydrazinecarbonyl)-6-methylphenyl)-1,3-dimethyl-1 H-pyrazole-4-carboxamide with different aldehydes or ketones in ethanol at room temperature is presented, the results of the study suggested that the pyrazole amide derivatives containing hydrazone moieties could inhibit the growth of G. zeae, F. oxysporium and C. mandshurica to a certain extent.

No MeSH data available.


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The commercialised pesticide of pyrazole amide and hydrazone derivatives.
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Figure 1: The commercialised pesticide of pyrazole amide and hydrazone derivatives.

Mentions: Pyrazole amide derivatives play an important role in development of medicine and pesticide due to their broad spectrum of biological activity[3-8]. Considerable attention for the study of synthesis and biological activity of pyrazole amide derivatives has been paid in recent years[9]. Currently, some pyrazole amide derivatives have been developed and commercialized as pesticide. As shown in Figure 1, furametpyr, penthiopyrad, tolfenpyrad, and chlorantraniliprole are known for their ability to protect certain plants from severe diseases and pests. In the past few years, hydrazone derivatives has been also attracted more and more attention due to their particular physical, chemical, and biological activities[10]. Hydrazone, a class of important substructure, can be found in numerous pharmaceutically active compounds[10,11], and have been demonstrated to bear important biological activities (such as antibacterial activity[12,13], analgesic activity[14], antinociceptive activity[15], insecticidal activity[16,17], antimalarial activity[18], and antimicrobial activity[19,20]). Some of the compounds containing hydrazone substructure have been commercialized as pesticides (such as benquinox, diflufenzopyr, and ferimzone) (Figure 1). In our recent publications[21,22], several hydrazone derivatives have been synthesized and tested for their insecticidal activity and antibacterial activity, some of the hydrazone derivatives exhibited notable insecticidal activity against Plutella xylostellaHelicoverpa armigeraCulex pipiens pallensLaphygma exiguaSpodoptera lituraNilaparvata lugens and Rhopalosiphum maidis[21], and some of the hydrazone derivatives containing a pyridine moiety possessed good antibacterial activity against Ralstonia Solanacearum[22].


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

Wu J, Wang J, Hu D, He M, Jin L, Song B - Chem Cent J (2012)

The commercialised pesticide of pyrazole amide and hydrazone derivatives.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3539435&req=5

Figure 1: The commercialised pesticide of pyrazole amide and hydrazone derivatives.
Mentions: Pyrazole amide derivatives play an important role in development of medicine and pesticide due to their broad spectrum of biological activity[3-8]. Considerable attention for the study of synthesis and biological activity of pyrazole amide derivatives has been paid in recent years[9]. Currently, some pyrazole amide derivatives have been developed and commercialized as pesticide. As shown in Figure 1, furametpyr, penthiopyrad, tolfenpyrad, and chlorantraniliprole are known for their ability to protect certain plants from severe diseases and pests. In the past few years, hydrazone derivatives has been also attracted more and more attention due to their particular physical, chemical, and biological activities[10]. Hydrazone, a class of important substructure, can be found in numerous pharmaceutically active compounds[10,11], and have been demonstrated to bear important biological activities (such as antibacterial activity[12,13], analgesic activity[14], antinociceptive activity[15], insecticidal activity[16,17], antimalarial activity[18], and antimicrobial activity[19,20]). Some of the compounds containing hydrazone substructure have been commercialized as pesticides (such as benquinox, diflufenzopyr, and ferimzone) (Figure 1). In our recent publications[21,22], several hydrazone derivatives have been synthesized and tested for their insecticidal activity and antibacterial activity, some of the hydrazone derivatives exhibited notable insecticidal activity against Plutella xylostellaHelicoverpa armigeraCulex pipiens pallensLaphygma exiguaSpodoptera lituraNilaparvata lugens and Rhopalosiphum maidis[21], and some of the hydrazone derivatives containing a pyridine moiety possessed good antibacterial activity against Ralstonia Solanacearum[22].

Bottom Line: Their structures were characterized by 1 H-NMR, 13 C-NMR, IR, and elemental analysis.The activity of compounds 7a, 7f, 7g, 7h, 7i, 7j, 7l and 7q were 40.82%, 47.78%, 50.32%, 40.82%, 49.05%, 48.73%, 40.19% and 45.89%, respectively, and the synthesized compounds showed certain antifungal activities against F. oxysporum and C.mandshurica.A practical synthetic route to pyrazole amide derivatives containing a hydrazone moiety were synthesized by the condensation of intermediates 5-chloro-N-(4-subsititued-2-(hydrazinecarbonyl)-6-methylphenyl)-1,3-dimethyl-1 H-pyrazole-4-carboxamide with different aldehydes or ketones in ethanol at room temperature is presented, the results of the study suggested that the pyrazole amide derivatives containing hydrazone moieties could inhibit the growth of G. zeae, F. oxysporium and C. mandshurica to a certain extent.

View Article: PubMed Central - HTML - PubMed

Affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, China. basong@gzu.edu.cn.

ABSTRACT

Background: The plant pathogenic fungus (such as Gibberella zeae, Fusarium oxysporum and Cytospora mandshurica) causes devastating disease in agriculture. The pathogenic fungus is responsible for billions of dollars in economic losses worldwide each year. In order to discover new fungicidal molecule with good fungicidal activity against G. zeae, F. oxysporum, and C. mandshurica, we sought to combine the active sub-structure of hydrazone and pyrazole amide derivatives together to design and synthesize novel pyrazole amide derivatives containing a hydrazone moiety.

Results: A series of novel pyrazole amide derivatives bearing hydrazone moiety were synthesized. Their structures were characterized by 1 H-NMR, 13 C-NMR, IR, and elemental analysis. The preliminary biological assays revealed that most of the synthesized compounds exhibit favorable antifungal activities against G. zeae. The activity of compounds 7a, 7f, 7g, 7h, 7i, 7j, 7l and 7q were 40.82%, 47.78%, 50.32%, 40.82%, 49.05%, 48.73%, 40.19% and 45.89%, respectively, and the synthesized compounds showed certain antifungal activities against F. oxysporum and C.mandshurica.

Conclusion: A practical synthetic route to pyrazole amide derivatives containing a hydrazone moiety were synthesized by the condensation of intermediates 5-chloro-N-(4-subsititued-2-(hydrazinecarbonyl)-6-methylphenyl)-1,3-dimethyl-1 H-pyrazole-4-carboxamide with different aldehydes or ketones in ethanol at room temperature is presented, the results of the study suggested that the pyrazole amide derivatives containing hydrazone moieties could inhibit the growth of G. zeae, F. oxysporium and C. mandshurica to a certain extent.

No MeSH data available.


Related in: MedlinePlus