Citation: Jing-Bo LIU, Na QIN, Yuan-Hong WANG, Yu-Xin LI, Zheng-Ming LI. Synthesis, Crystal Structure and Insecticidal Activities of (4aR, 7aS)-6-Benzyl-1-((R)-2-(2-chlorophenyl)-4, 5-dihydrothiazole- 4-carbonyl)hexahydro-5H-pyrrolo[3, 4-b]pyridine-5, 7(6H)-dione[J]. Chinese Journal of Structural Chemistry, ;2021, 40(5): 659-665. doi: 10.14102/j.cnki.0254–5861.2011–2974 shu

Synthesis, Crystal Structure and Insecticidal Activities of (4aR, 7aS)-6-Benzyl-1-((R)-2-(2-chlorophenyl)-4, 5-dihydrothiazole- 4-carbonyl)hexahydro-5H-pyrrolo[3, 4-b]pyridine-5, 7(6H)-dione

Jing-Bo LIU ^{a, b,,} ,
Na QIN ^a ,
Yuan-Hong WANG ^a ,
Yu-Xin LI ^b,, ,
Zheng-Ming LI ^b

a.
College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300384, China
b.
State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Jing-Bo LIU, liujingbo0626@163.com Yu-Xin LI, liyx128@nankai.edu.cn
Received Date: 1 September 2020
Accepted Date: 4 October 2020

Fund Project: the Natural Science Foundation of Tianjin 19JCQNJC04600National Natural Science Foundation of China 31901908National Natural Science Foundation of China 31972287the Scientific Research and Development Fund Project of Tianjin Agricultural University 20190108

Figures(4)

The title compound (4aR, 7aS)-6-benzyl-1-((R)-2-(2-chlorophenyl)-4, 5-dihydrothiazole-4-carbonyl)- hexahydro-5H-pyrrolo[3, 4-b]pyridine-5, 7(6H)-dione (C₂₄H₂₂ClN₃O₃S) was synthesized, and its chemical structure was confirmed by ¹H NMR, ¹³C NMR and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic system, space group C2/c with a = 28.929(6), b = 7.858(16), c = 22.936(5) Å, β = 125.20(3)°, V = 4221.4(15) Å³, Z = 8, D_c = 1.473 g/cm³, μ(MoKa) = 0.314 mm^–1, the final R = 0.0629 and wR = 0.1708 for 2812 observed reflections with I > 2σ(I). The preliminary insecticidal activity indicated that the title compound exhibited good and promising insecticidal activities against Mythimna separata, Plutella xylostella and Culex pipiens pallens. Moreover, the calcium imaging experiment indicated that the title compound can activate intracellular calcium channels to release the stored calcium ion from endoplasmic reticulum (ER) to cytoplasm of Mythimna separata.
- synthesis,
- crystal structure,
- insecticidal activity,
- calcium imaging
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