Citation: Wei-Bo WANG, Xiao-Yu LIU, Zhi-Xinyi LI, Wei GAO, You LV, Kun LI, Tatiana V. GLUKHAREVA, Liang-Fu TANG, Zhi-Jin FAN. Synthesis, Crystal Structure and Fungicidal Activity of 3, 4-Dichloro-5-(6-chloro-9-(4-fluorobenzyl)-9H-purin-8-yl)isothiazole[J]. Chinese Journal of Structural Chemistry, ;2022, 41(2): 220209. doi: 10.14102/j.cnki.0254-5861.2011-3235 shu

Synthesis, Crystal Structure and Fungicidal Activity of 3, 4-Dichloro-5-(6-chloro-9-(4-fluorobenzyl)-9H-purin-8-yl)isothiazole

Wei-Bo WANG ^{a, b} ,
Xiao-Yu LIU ^{a, b} ,
Zhi-Xinyi LI ^c ,
Wei GAO ^{a, b} ,
You LV ^{a, b} ,
Kun LI ^{a, b} ,
Tatiana V. GLUKHAREVA ^d,, ,
Liang-Fu TANG ^{a, b} ,
Zhi-Jin FAN ^{a, b,,}

a.
State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
b.
Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China
c.
School of Medicine, Nankai University, Tianjin 300071, China
d.
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

^th

Received Date: 26 April 2021
Accepted Date: 1 June 2021

Fund Project: the Tianjin Natural Science Foundation 18JCZDJC33500the Frontiers Science Center for New Organic Matter, Nankai University 63181206

Figures(4)

3, 4-Dichloro-5-(6-chloro-9-(4-fluorobenzyl)-9H-purin-8-yl)isothiazole, a novel purine derivative, was synthesized by the cyclization of pyrimidine amine. Its structure was characterized by ¹H NMR, ¹³C NMR, ¹⁹F NMR, H RMS and single-crystal X-ray diffraction. This compound 3 is crystallized from a mixed solvent of dichloromethane and n-hexane (1:2, v/v) for structural identification as monoclinic crystal system, space group P2₁/n with a = 11.66250(10), b = 8.21300(10), c = 17.77920(10) Å, V = 1676.34(3) Å³, Z = 4, D_c = 1.643 g/cm³, F(000) = 832.0 and μ = 6.301 mm^-1. 22315 reflections were measured (8.43≤2θ≤158.10°), of which 3532 were unique (R_int = 0.0311) and used in all calculations. The final R = 0.0334 (I > 2σ(I)) and wR = 0.0842 (reflections). The title compound showed over 50% of growth inhibition against Botrytis cinereal, Cercospora arachidicola, Gibberella zeae, Rhizoctonia solani and Sclerotinia sclerotiorum at 50 mg/L, and its EC₅₀ value against R. solani was 60.44 µmol/L, which was active at the same level as that of positive control diflumetorim with its EC₅₀ value of 60.29 µmol/L and less active than YZK-C22 with its EC₅₀ value of 12.32 µmol/L, respectively. Our studies discovered that the combination of bioactive substructures of isothiazole with purine could be an effective way to novel fungicide development.
- purine,
- synthesis,
- crystal structure,
- fungicidal activity
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