Synthesis, Crystal Structure and Fungicidal Activity of 3-Chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2H-chromen-2-ones

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摘要: 3-Chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2H-chromen-2-ones, a kind of coumarin derivatives, were synthesized by β-ketoester formation and cyclization. Target compound 5e was crystallized from methanol for structural identification as monoclinic crystal system, space group C2/c with a = 16.2700(6), b = 7.1801(5), c = 23.4861(10) Å, V = 2742.6(2) Å3, Z = 8, Dc = 1.756 g/cm3, F(000) = 1456 and μ = 0.827 mm-1. 8308 Reflections were collected (6.01≤2θ≤50.05°), of which 2428 were unique (Rint = 0.0432) and used in all calculations. The final R = 0.0408 (I > 2σ(I)) and wR = 0.1056 (reflections). In vitro bioassay indicated that compounds 5d & 5e possessed good activity against Botrytis cinerea, Physalospora piricola, Rhizoctonia solani, and Sclerotinia sclerotiorum with lower EC50 values falling between 0.50 and 4.85 µg/mL than that of positive control osthole with its EC50 values between 7.38 and 74.59 µg/mL. In vivo screening showed that 5e exhibited 98% and 95% efficacy against Pseudoperonospora cubensis (Berk. & Curt.) Rostov. at 100 and 50 µg/mL, respectively. Our studies discovered that the combination of bioactive substructures of isothiazole with coumarin was an effective way to novel fungicide development.

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	吕游
	李坤
	郝泽生
	KALININA Tatiana A.
	GLUKHAREVA Tatiana V.
	范志金

关键词: coumarin, synthesis, crystal structure, fungicidal activity

Abstract:3-Chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2H-chromen-2-ones, a kind of coumarin derivatives, were synthesized by β-ketoester formation and cyclization. Target compound 5e was crystallized from methanol for structural identification as monoclinic crystal system, space group C2/c with a = 16.2700(6), b = 7.1801(5), c = 23.4861(10) Å, V = 2742.6(2) Å3, Z = 8, Dc = 1.756 g/cm3, F(000) = 1456 and μ = 0.827 mm-1. 8308 Reflections were collected (6.01≤2θ≤50.05°), of which 2428 were unique (Rint = 0.0432) and used in all calculations. The final R = 0.0408 (I > 2σ(I)) and wR = 0.1056 (reflections). In vitro bioassay indicated that compounds 5d & 5e possessed good activity against Botrytis cinerea, Physalospora piricola, Rhizoctonia solani, and Sclerotinia sclerotiorum with lower EC50 values falling between 0.50 and 4.85 µg/mL than that of positive control osthole with its EC50 values between 7.38 and 74.59 µg/mL. In vivo screening showed that 5e exhibited 98% and 95% efficacy against Pseudoperonospora cubensis (Berk. & Curt.) Rostov. at 100 and 50 µg/mL, respectively. Our studies discovered that the combination of bioactive substructures of isothiazole with coumarin was an effective way to novel fungicide development.

Key words: coumarin synthesis crystal structure fungicidal activity

收稿日期: 2021-01-21 出版日期: 2021-07-28

基金资助:This work was supported in part by the Tianjin Natural Science Foundation (No. 18JCZDJC33500), the National Natural Science Foundation of China (No. 31872007) and the Tianjin Development Program for Innovation and Entrepreneurship

通讯作者: fanzj@nankai.edu.cn E-mail: fanzj@nankai.edu.cn

引用本文:

吕游;李坤;郝泽生;KALININA Tatiana A.;GLUKHAREVA Tatiana V.;范志金. Synthesis, Crystal Structure and Fungicidal Activity of 3-Chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2H-chromen-2-ones[J]. 结构化学, 2021, 40(8): 1068-1074.
LV You;LI Kun;HAO Ze-Sheng;KALININA Tatiana A.;GLUKHAREVA Tatiana V.;FAN Zhi-Jin. Synthesis, Crystal Structure and Fungicidal Activity of 3-Chloro-4-(3,4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2H-chromen-2-ones. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2021, 40(8): 1068-1074.

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http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2021/V40/I8/1068

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