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Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

Postal Subscription Code 80-969

2018 Impact Factor: 2.809

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Front. Chem. Sci. Eng.    2019, Vol. 13 Issue (2) : 369-376    https://doi.org/10.1007/s11705-018-1734-7
RESEARCH ARTICLE
The synthesis of 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives and their antifungal activity against Pyricularia oryzae
Long Cheng1,2, Ruirui Zhang2, Hongke Wu1, Xinghai Liu1(), Tianming Xu2()
1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
2. Zhejiang Base of National Southern Pesticide Research Centre, Zhejiang Research Institute of Chemical Industry, Hangzhou 310023, China
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Abstract

A series of novel 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives were designed and synthesized. Bioassay results showed that some of them exhibited good activity against Pyricularia oryzae (P. oryzae). It was found that the compound 5q (benzyl (6-(tert-butyl)-8-fluoro-2,3-dimethylquinolin-4-yl) carbonate) possessed good activity against P. oryzae whatever protective activity (10 mg·L−1) or curative activity (25 mg·L−1), which was better than that of control tebufloquin. In addition, the frontier molecular orbit results revealed that the compound held higher activity against P. oryzae when the total energy was low and the ClogP was high, which may provide useful information for further design novel fungicides.
Keywords quinoline      synthesis      antifungal activity      rice blast      SAR     
Corresponding Author(s): Xinghai Liu,Tianming Xu   
Online First Date: 17 July 2018    Issue Date: 22 May 2019
 Cite this article:   
Long Cheng,Ruirui Zhang,Hongke Wu, et al. The synthesis of 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives and their antifungal activity against Pyricularia oryzae[J]. Front. Chem. Sci. Eng., 2019, 13(2): 369-376.
 URL:  
https://academic.hep.com.cn/fcse/EN/10.1007/s11705-018-1734-7
https://academic.hep.com.cn/fcse/EN/Y2019/V13/I2/369
Fig.1  Scheme 1 Design strategy of the title compounds
Fig.2  Scheme 2 The synthetic route of title compounds
No. R 100/(mg?L?1) 50/(mg?L?1) 10/(mg?L?1)
5a 4-Me 100 95 65
5b 4-Br 100 80 55
5c 3,4-Cl2 100 85 70
5d 4-OMe 100 99 65
5e 4-F 100 90 80
5f 4-Cl 100 85 45
5g 2,4-Cl2 100 80 30
5h 2-Cl 100 65 35
5i 2-F 100 75 30
5j 2-Me 100 75 40
5k 3-Me 100 75 45
5l 3-F 100 70 34
5m 2,6-Cl2 100 85 45
5n 2,4-F2 100 90 75
5o 2-Cl-6-F 95 70 50
5p 2-Cl-5-CF3 100 75 45
5q H 100 95 75
Tebufloquin 100 70 0
Tab.1  The in vivo protective efficacy against rice blast at different concentration
No. R 100/(mg?L?1) 50/(mg?L?1) 25/(mg?L?1)
5a 4-Me 85 65 25
5b 4-Br 80 45 0
5c 3,4-Cl2 90 75 45
5d 4-OMe 85 65 35
5e 4-F 85 65 35
5f 4-Cl 65 35 0
5g 2,4-Cl2 80 45 0
5h 2-Cl 75 35 0
5i 2-F 85 50 0
5j 2-Me 65 55 25
5k 3-Me 90 45 0
5l 3-F 75 35 0
5m 2,6-Cl2 85 40 0
5n 2,4-F2 75 70 0
5o 2-Cl-6-F 75 35 0
5p 2-Cl-5-CF3 75 45 0
5q H 90 65 45
Tebufloquin 70 45 0
Tab.2  The in vivo curative efficacy against rice blast at different concentration
Compound EC50/(mg?L?1) Y = BX + A R
5a 2.79(1.72–4.58) 4.7522+ 0.5567X 0.98
5c 3.59(2.31–5.82) 4.6658+ 0.6018X 0.98
5d 0.94(0.61–1.37) 5.0203+ 0.7815X 0.98
5e 6.77(4.93–9.57) 4.2012+ 0.9621X 0.99
5q 5.18(3.68–7.66) 4.4027+ 0.8363X 0.99
Tebufloquin 1.27(0.91–1.70) 4.8943+ 1.0124X 0.99
Tab.3  The EC50 of high active compound against rice blast (in vitro)
DFT 5q 5d Tebufloquin
Etotal/Hartreea ?1270.85620776 ?1385.33947946 ?1865.96608237
EHOMO/Hartree ?0.22710 ?0.22504 ?0.22894
ELUMO/Hartree ?0.05235 ?0.05014 ?0.07096
DEb/Hartree 0.17475 0.1749 0.15798
CLogP 6.33 6.95 4.81
Tab.4  CLogP, total energy, energy gap and frontier orbital energy
Fig.3  Frontier molecular orbitals of compound 5q, 5d and tebufloquin
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