98198-65-3Relevant articles and documents
Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring
Yan, Zhongzhong,Liu, Aiping,Huang, Mingzhi,Liu, Minhua,Pei, Hui,Huang, Lu,Yi, Haibo,Liu, Weidong,Hu, Aixi
, p. 170 - 181 (2018/03/08)
Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole carboxamide derivatives with antifungal activity were synthesized. Those compounds were evaluated against five phytopathogenic fungi, Gibberella zeae, Phytophythora capsici, Sclerotonia sclerotiorum, Erysiphe graminis and Puccinia sorghi. The results indicated that most of the compounds displayed good fungicidal activities, especially against E. graminis. Theoretical calculations were carried out at the B3LYP/6-31G (d, p) level and the full geometry optimization was carried out using the 6-31G (d, p) basis set, and the frontier orbital energy, atomic net charges, molecular docking were discussed, and the structure-activity relationships were also studied.
Design, Synthesis, and Acaricidal Activities of Novel Pyrazole Acrylonitrile Compounds
Huang, Danling,Huang, Mingzhi,Liu, Aiping,Liu, Xingping,Liu, Weidong,Chen, Xiaoyang,Xue, Hansong,Sun, Jiong,Yin, Dulin,Wang, Xiaoguang
, p. 1121 - 1128 (2017/03/27)
Using cyenopyrafen as the lead compound, a series of novel pyrazole acrylonitrile compounds were designed and synthesized via the reaction of butylphenylacetonitrile with the corresponding (substituted pyrazol-5-yl) methanone of pyrethroid alcohols in the presence of potassium tert-butoxide. These compounds showed prominent acaricidal activity against Tetranchus urticae. In particular, IIf, IIh, IIo, and IIp displayed excellent activities, which the median lethal concentrations were all lower 0.4 mg/L. In addition, the structure-activity relationship for the target compounds was discussed.
Synthesis and insecticidal activities of novel 1H-pyrazole-5-carboxylic acid derivatives
Huang, Danling,Liu, Aiping,Liu, Weidong,Liu, Xingping,Ren, Yeguo,Zheng, Xi,Pei, Hui,Xiang, Jun,Huang, Mingzhi,Wang, Xiaoguang
, p. 455 - 460 (2017/12/18)
Fourteen 1H-pyrazole-5-carboxylic acid derivatives containing oxazole and thiazole rings were synthesized and characterized by 1H NMR, mass spectrometry and elemental analysis. Most target compounds were obtained in overall yields in the range of 30-50%. The insecticidal activities of these new compounds against Aphis fabae were evaluated. The bioassays' results indicate that some of these compounds exhibit good activities, especially compound 7h which shows 85.7% mortality against A. fabae at a concentration of 12.5 mg/L. This activity is comparable to that of the commercial insecticide imidacloprid.
Design, synthesis and biological evaluation of 1H-pyrazole-5-carboxamide derivatives as potential fungicidal and insecticidal agents
Huang, Danling,Huang, Mingzhi,Liu, Weidong,Liu, Aiping,Liu, Xingping,Chen, Xiaoyang,Pei, Hui,Sun, Jiong,Yin, Dulin,Wang, Xiaoguang
, p. 2053 - 2061 (2017/09/30)
A series of novel 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety were designed and synthesized by a facile method, and their structures were characterized by 1H NMR, mass spectrometry and elemental analysis. Bioassay results showed that most of the title compounds showed potent fungicidal activities against Erysiphe graminis and insecticidal activity against Aphis fabae. Especially, compound 9b has EC50 values of 3.04 mg/L against Erysiphe graminis, of which the fungicidal activity is better than that of the commercial fungicide Thifluzamide and Azoxystrobinare; compound 9l has LC50 values of 3.81 mg/L against Aphis fabae, which was comparable with the commercial insecticide Tolfenpyrad. It is suggested that 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety could be considered as a precursor structure for further design of pesticides. Graphical Abstract: A series of novel 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety were designed and synthesized by a facile method, and their structures were characterized by 1H NMR, mass spectrometry and elemental analysis. Bioassay results showed that most of the title compounds showed potent fungicidal activities against Erysiphe graminis and insecticidal activity against Aphis fabae. Especially, compound 9b has EC50 values of 3.04 mg/L against Erysiphe graminis, of which the fungicidal activity is better than that of the commercial fungicide Thifluzamide and Azoxystrobinare; compound 9l has LC50 values of 3.81 mg/L against Aphis fabae, which was comparable with the commercial insecticide Tolfenpyrad. It is suggested that 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety could be considered as a precursor structure for further design of pesticides.[Figure not available: see fulltext.]
