Citation: Zhi-Bing Wu, Xiang Zhou, Yi-Qiang Ye, Pei-Yi Wang, Song Yang. Design, synthesis and insecticidal activities of novel 1-substituted-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives[J]. Chinese Chemical Letters, ;2017, 28(1): 121-125. doi: 10.1016/j.cclet.2016.06.010 shu

Design, synthesis and insecticidal activities of novel 1-substituted-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives

Zhi-Bing Wu ^a ,
Xiang Zhou ^a ,
Yi-Qiang Ye ^a ,
Pei-Yi Wang ^a ,
Song Yang ^a,b,,

a.
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, China
b.
College of Pharmacy, East China University of Science & Technology, Shanghai 200237, China

Corresponding author: Song Yang, jhzx.msm@gmail.com
Received Date: 6 April 2016
Revised Date: 19 May 2016
Accepted Date: 20 May 2016
Available Online: 11 January 2016

Figures(3)

A series of novel 5-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives (6a-6n, 7a, 7b, and 8a-8f) were synthesised by placing the amide bond at the 4-position of the pyrazole ring. These derivatives differed from the structure of chlorantraniliprole analogues with the amide bond at the 5-position of the pyrazole ring. Preliminary bioassay results revealed that a few title compounds exhibited good insecticidal activities against lepidopteran pests, such as Plutella xylostella, Mythimna separate, Heliothis armigera, and Ostrinia nubilalis. Some title compounds also elicited broad-spectrum insecticidal activities against dipterous insects including Culex pipiens pallens after altering the amide position. Similar to pyrazole-5-carboxamide analogues, compounds 6b and 6e showed 100% insecticidal activity against P. xylostella, C. pipiens pallens, and M. separate at concentrations of 200, 2, and 200 μg/mL, respectively. This finding suggested that 5-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives are potential alternative insecticides for management of agriculture pests.
- 5-(Trifluoromethyl)-1H-pyrazole-4-carboxamide,
- Insecticidal activities,
- Chlorantraniliprole,
- Ryanodine receptors
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