The synthesis of 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives and their antifungal activity against Pyricularia oryzae

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.

Graphical abstract

Keywords

quinoline / synthesis / antifungal activity / rice blast / SAR

References

[1] Kramer W, Schirmer U. Modern Crop Protection Compounds.Weinheim: Wiley-VCH, 2007, 1141

[2] Gobeil-Richard M, Tremblay D M, Beaulieu C, Van der Heyden H, Carisse O. A pyrosequencing-based method to quantify genetic substitutions associated with resistance to succinate dehydrogenase inhibitor fungicides in Botrytis spp. populations. Pest Management Science, 2016, 72(3): 566–573

[3] Hidalgo W, Cano M, Arbelaez M, Zarrazola E, Gil J, Schneider B, Otálvaro F. 4-Phenylphenalenones as a template for new photodynamic compounds against Mycosphaerella fijiensis. Pest Management Science, 2016, 72(4): 796–800

[4] Johnson P L, Kister J, Thornburgh S. Improved synthetic route to quinoxyfen photometabolite 2-chloro-10-fluorochromeno[2,3,4-de]quinoline. Pest Management Science, 2017, 73(8): 1703–1708

[5] Bellón-Gómez D, Vela-Corcía D, Pérez-García A, Torés J A. Sensitivity of Podosphaera xanthii populations to anti-powdery-mildew fungicides in Spain. Pest Management Science, 2015, 71(10): 1407–1413

[6] Matsumura M, Mitomi M, Yabusaki M B. Actericidal Mixed Composition for Agriculture and Horticulture.JP Patent, 2 007 112 760, 2005

[7] Kiguchi S, Tanaka S, Ozawa M, Iwata A. Plant disease controlling composition and method for controlling plant disease.US Patent, 8940717, 2015

[8] Nakajima Y, Okawara Y. Pesticidal composition containing condensed heterocyclic compound and other agrochemically active component, and pest control method.JP Patent, 2 016 102 104, 2016

[9] Shi X, Kou P, Li M, Zhao H, Wu X, Da P, Mei H, Liang B, Lu H, Zhou D, Composition for preventing and treating rice blast, comprises fenaminstrobin and isotianil, carpropamid, 4,5,6,7-tetrachlorophthalide or tebufloquin.CN Patent, 103 271 076, 2014

[10] Sakurais O, Morimoto M, Kondon I. Plant disease control composition useful for controlling plant disease from plant pathogens such as rice blast caused by Pyricularia oryzae, comprises quinoline compounds and fungicidal compound e.g. fluxapyroxad and benzovindiflupyr.WO Patent, 2 015 141 867, 2015

[11] Kimura N.Composition contains carboxamide compound, isotianil, diclocymet, probenazole, orysastrobin, tiadinil, tricyclazole, sulfoxaflor, dinotefuran, thiamethoxam, imidacloprid, fipronil, tetraniliprole and spinosad.JP Patent, 2 015 214 554, 2015

[12] Jain P P, Degani M S, Raju A, Anantram A, Seervi M, Sathaye S, Ray M, Rajan M G R. Identification of a novel class of quinoline-oxadiazole hybrids as anti-tuberculosis agents. Bioorganic & Medicinal Chemistry Letters, 2016, 26(2): 645–649

[13] Kamath P R, Sunil D, Ajees A A. Synthesis of indole-quinoline-oxadiazoles: their anticancer potential and computational tubulin binding studies. Research on Chemical Intermediates, 2016, 42(6): 5899–5914

[14] Puskullu M O, Shirinzadeh H, Nenni M, Gurer-Orhan H, Suzen S. Synthesis and evaluation of antioxidant activity of new quinoline-2-carbaldehyde hydrazone derivatives: bioisosteric melatonin analogues. Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, 31(1): 121–125

[15] Ghodsi R, Azizi E, Ferlin M G, Pezzi V, Zarghi A. Design, synthesis and biological evaluation of 4-(imidazolylmethyl)-2-aryl-quinoline derivatives as aromatase inhibitors and anti-breast cancer agents. Letters in Drug Design & Discovery, 2016, 13(1): 89–97

[16] Di Pietro O, Vicente-García E, Taylor M C, Berenguer D, Viayna E, Lanzoni A, Sola I, Sayago H, Riera C, Fisa R, Clos M V, Pérez B, Kelly J M, Lavilla R, Muñoz-Torrero D. Multicomponent reaction-based synthesis and biological evaluation of tricyclic heterofused quinolines with multi-trypanosomatid activity. European Journal of Medicinal Chemistry, 2015, 105: 120–137

[17] Coa J C, Castrillón W, Cardona W, Carda M, Ospina V, Muñoz J A, Vélez I D, Robledo S M. Synthesis, leishmanicidal, trypanocidal and cytotoxic activity of quinoline-hydrazone hybrids. European Journal of Medicinal Chemistry, 2015, 101: 746–753

[18] Huang X, Bao Y, Zhu S, Zhang X, Lan S, Wang T. Synthesis and biological evaluation of levofloxacin core-based derivatives with potent antibacterial activity against resistant Gram-positive pathogens. Bioorganic & Medicinal Chemistry Letters, 2015, 25(18): 3928–3932

[19] Yan S L, Yang M Y, Sun Z H, Min L J, Tan C X, Weng J Q, Wu H K, Liu X H. Synthesis and antifungal activity of 1,2,3-thiadiazole derivatives containing 1,3,4-thiadiazole moiety. Letters in Drug Design & Discovery, 2014, 11(7): 940–943

[20] Zhang L J, Yang M Y, Sun Z H, Tan C X, Weng J Q, Wu H K, Liu X H. Synthesis and antifungal activity of 1,3,4-thiadiazole derivatives containing pyridine group. Letters in Drug Design & Discovery, 2014, 11(9): 1107–1111

[21] Fang Y M, Zhang R R, Shen Z H, Tan C X, Weng J Q, Xu T M, Liu X H, Huang H Y, Wu H K. Synthesis and antifungal activity of some 6-tert-butyl-8-chloro-2,3-dimethylquinolin-4-ol derivatives against Pyricularia oryae. Letters in Drug Design & Discovery, 2018, 15:

[22] Fang Y M, Zhang R R, Shen Z H, Wu H K, Tan C X, Weng J Q, Xu T M, Liu X H. Synthesis, antifungal activity, and SAR study of some new 6-perfluoropropanyl quinoline derivatives. Journal of Heterocyclic Chemistry, 2018, 55(1): 240–245

[23] Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, . Gaussian 03, revision C. 01; Gaussian, Inc.: Wallingford, CT, USA, 2004

[24] Liu X H, Fang Y M, Xie F, Zhang R R, Shen Z H, Tan C X, Weng J Q, Xu T M, Huang H Y. Synthesis and in vivo fungicidal activity of some new quinoline derivatives against rice blast. Pest Management Science, 2017, 73(9): 1900–1907

Acknowledgements

This work was supported financially by Zhejiang Provincial Natural Science Foundation of China (No. LY16C140007) and Research Institute Special Program of Department of Science and Technology of Zhejiang Province (No. 2015F50030).

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