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Citation: MAO Wu-Tao, ZONG Guang-Ning, FAN Zhi-Jin, LI Feng-Yun, SONG Hai-Bin, LI Juan-Juan, Kalinina A. Tatiana, Khazhieva Inna, Lugovik Ksenia, Morzherin Yu. Yury, Belskaya P. Nataliya. Synthesis, Crystal Structure and Biological Activity of N-cyanosulfoximine Derivative Containing 1,2,3-Thiadiazole[J]. Chinese Journal of Structural Chemistry, ;2015, 34(9): 1428-1433. doi: 10.14102/j.cnki.0254-5861.2011-0665 shu

Synthesis, Crystal Structure and Biological Activity of N-cyanosulfoximine Derivative Containing 1,2,3-Thiadiazole

1.
a State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China;
2.
b College of Chemistry and Pharmacy Engineering, Nanyang Normal University, Henan 473061, China;
c The Ural Federal University Named after the First President of Russia B.
c The Ural Federal University Named after the First President of Russia B. N. Yeltsin, Yeltsin UrFU 620002, Ekaterinburg, Russia

Received Date: 10 February 2015
Available Online: 9 July 2015
Fund Project: This study was funded in part by the National Natural Science Foundation of China (21372132) (21372132)

The title compound N-cyanosulfoximine derivative containing 1,2,3-thiadiazole (C₆H₈N₄OS₂, M_r=216.28) has been synthesized using 4-(chloromethyl)-5-methyl-1,2,3-thiadiazole as the starting material, and its structure was characterized by IR, ¹H NMR, HRMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to orthorhombic, space group Pna2₁ with a=14.730(6), b=5.478(2), c=22.619(9) Å, Z=8, V=1825.0(13) Å³, D_c=1.574 g/cm³, μ=0.547 mm^-1, F(000)=896, R=0.0767 and wR (I>2σ(I))=0.2064. X-ray analysis indicates that in this crystal double enantiomers are found as the basically asymmetrical unit and interactions between S(1)···N(3), S(3)···N(4) and S(3)···N(7) are observed. This kind of interactions extends the molecules into a one-dimensional double chain. The preliminary biological test showed that the title compound had insecticidal activity against Myzus persicae in a certain degree and also presented moderate potential bioactivity against tobacco mosaic virus (TMV).
- 1,2,3-thiadiazole,
- sulfoximine,
- crystal structure,
- synthesis,
- biological activity
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