Citation: Yu Fuqiang, Guan Aiying, Sun Xufeng, Li Huichao, Li Xiaowu. Design, Synthesis and Fungicidal Activity against Rhizoctonia solani of New Phenylpyrazoloxyl Propionic Acid Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 397-405. doi: 10.6023/cjoc201807009 shu

Design, Synthesis and Fungicidal Activity against Rhizoctonia solani of New Phenylpyrazoloxyl Propionic Acid Derivatives

Yu Fuqiang ^a,b ,
Guan Aiying ^b,, ,
Sun Xufeng ^b ,
Li Huichao ^b ,
Li Xiaowu ^a,,

a.
Key Laboratory for Anisotropy and Texture of Materials, Ministry of Education, Department of Materials Physics and Chemistry, School of Material Science and Engineering, Northeastern University, Shenyang 110819
b.
State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R & D. Co. Ltd., Tiexi District, Shenyang 110021

Corresponding author: Guan Aiying, guanaiying@sinochem.com Li Xiaowu, xwli@mail.neu.edu.cn
Received Date: 4 July 2018
Revised Date: 5 September 2018
Available Online: 14 February 2018
Fund Project: Project supported by the Liaoning Provincal Science and Technology Plan Projects No.2015306001Project supported by the Liaoning Provincal Science and Technology Plan Projects (No. 2015306001)

Figures(3)

Rice sheath blight disease, one of three most important diseases in rice, can lead to crop production loss seriously. However, the application of fungicides is an effective way to prevent rice from diseases. After being used for a period of time, the plant pathogenic fungi may develop resistance to chemical fungicide, so it is necessary to discover compounds with novel structures and further to address the problem of fungicide resistance. By employing the intermediate derivatisation method (IDM), twenty-five new phenylpyrazoloxyl propionic acid derivatives were designed and synthesized. The biological activities of title compounds were tested against Rhizoctonia solani and their structure-activity relationships (SAR) were discussed as well. The preliminary bioassay results displayed that some compounds exhibited an excellent fungicidal activity against Rhizoctonia solani, especially 2-((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)-N-(4-nitrophenyl)propanamide (17) (EC₅₀=1.05 mg/L) and 2-((1-(4-chlorophenyl)-1H-pyrazol-3-yl)oxy)-N-(pyridin-2-yl)propanamide (22) (EC₅₀=1.02 mg/L) showing a com-parable activity to the commercial contrast tebuconazole (EC₅₀=1.02 mg/L), and 2-((1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy)-N-(3, 4-dichlorophenyl)propanamide (20) (EC₅₀=0.95 mg/L) is a little more active than tebuconazole (EC₅₀=1.02 mg/L).
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