Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (9): 2832-2839.DOI: 10.6023/cjoc202203051 Previous Articles     Next Articles

Special Issue: 有机氟化学虚拟合辑



李文娟a,*(), 张睿a, 蔡志华a, 韩小强b,*(), 何林a, 代斌a   

  1. a 石河子大学化学化工学院 新疆兵团化工绿色过程重点实验室 新疆石河子 832003
    b 石河子大学农学院 新疆绿洲农业病虫害治理与植物资源利用重点实验室 新疆石河子 832003
  • 收稿日期:2022-03-24 修回日期:2022-05-13 发布日期:2022-06-22
  • 通讯作者: 李文娟, 韩小强
  • 基金资助:
    石河子大学双一流(SHYL-YB201901); 石河子大学高层次人才启动(RCZK2021B08)

Constrution and Insecticidal Activities of Trifluoromethylated Benzocyclicsulfoximine Derivatives by [3+2] Cycloaddition Reaction of Beznyne

Wenjuan Lia(), Rui Zhanga, Zhihua Caia, Xiaoqiang Hanb(), Lin Hea, Bin Daia   

  1. a Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003
    b Key Laboratory for Oasis Agricultural Pest Management and Plant Protection Resources Utilization, Xinjiang Uygur Autonomous Region, College of Agriculture, Shihezi University, Shihezi, Xinjiang 832003
  • Received:2022-03-24 Revised:2022-05-13 Published:2022-06-22
  • Contact: Wenjuan Li, Xiaoqiang Han
  • Supported by:
    Double First Class Project of Shihezi University(SHYL-YB201901); High Level Talents Launch Project of Shehezi University(RCZK2021B08)

Sulfoximines derivatives are widely used in the field of pesticides and medicine due to its antimalarial, antibacterial and herbicidal properties. A concise and direct synthetic strategy for the construction of trifluoromethylated cyclicsulfoximines has been developed via [3+2] cycloaddition reaction of benzynes and trifluoromethyl α,β-unsaturated N-(S)-tert-butyl sulfinylketoimines. The reaction affords the cyclosulfoximines at room temperature in low to moderate yields (13%~57%) and KF as fluorinated reagent, 18-C-6 as additives, and acetonitrile and toluene as mixed solvent (VV=4∶1). The insecticidal activities against Aphis gossypii were determined by impregnation method. The results showed that 24-h median lethal concentrations (24 h LC50) of (1R,3S)-1-(tert-butyl)-3-((E)-4-methylstyryl)-3-(trifluoromethyl)-3H-1λ4-benzo- [d]isothiazole 1-oxide) (3b) and (1R,3S)-1-(tert-butyl)-3-(trifluoromethyl)-3-((E)-4-(trifluoromethyl)styryl)-3H-1λ4-benzo[d]- isothiazole 1-oxide (3h) are lower than that of the positive control imidacolprid (0.0800 mg/L) and dinitraz (0.0532 mg/L). They can be used as new lead insecticidal compounds with further structure modification.

Key words: benzyne, [3+2] cycloaddition, benzocyclicsulfoximine, insecticidal activity