Citation: You LV, Kun LI, Ze-Sheng HAO, Tatiana A. KALININA, Tatiana V. GLUKHAREVA, Zhi-Jin FAN. Synthesis, Crystal Structure and Fungicidal Activity of 3-Chloro-4-(3, 4-dichloroisothiazol-5-yl)-5-hydroxy-7-methyl-2H-chromen-2-ones[J]. Chinese Journal of Structural Chemistry, ;2021, 40(8): 1068-1074. doi: 10.14102/j.cnki.0254–5861.2011–3108 shu

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

a.
State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
b.
The Ural Federal University Named after the First President of Russia B. N. Yeltsin, Yeltsin UrFU 620002, Ekaterinburg, Russia

Corresponding author: Tatiana V. GLUKHAREVA, taniagluhareva@yandex.ru Zhi-Jin FAN, fanzj@nankai.edu.cn
Received Date: 21 January 2021
Accepted Date: 11 March 2021

Fund Project: the Tianjin Natural Science Foundation 18JCZDJC33500the National Natural Science Foundation of China 31872007

Figures(4)

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, D_c = 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 (R_int = 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.
- coumarin,
- synthesis,
- crystal structure,
- fungicidal activity
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