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

doi:10.6023/cjoc202203051

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

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苯炔[3+2]环加成反应构建三氟甲基取代的苯并环状亚砜亚胺衍生物及其杀棉蚜活性研究

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

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 Li^a(), Rui Zhang^a, Zhihua Cai^a, Xiaoqiang Han^b(), Lin He^a, Bin Dai^a

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)

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Abstract

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 (V∶V=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

Cite this article

Wenjuan Li, Rui Zhang, Zhihua Cai, Xiaoqiang Han, Lin He, Bin Dai. Constrution and Insecticidal Activities of Trifluoromethylated Benzocyclicsulfoximine Derivatives by [3+2] Cycloaddition Reaction of Beznyne[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2832-2839.

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Compd.	LC₅₀/(mg•L^–1)	Compd.	LC₅₀/(mg•L^–1)
3a	1.5976	3g	0.0860
3b	0.0246	3h	0.0077
3c	0.6820	3i	1.6558
3d	0.8489	Imidacolprid	0.0800
3e	0.3501	Dinitraz	0.0532
3f	0.4055

Compd.	LC₅₀/(mg•L^–1)	Compd.	LC₅₀/(mg•L^–1)
3a	1.5976	3g	0.0860
3b	0.0246	3h	0.0077
3c	0.6820	3i	1.6558
3d	0.8489	Imidacolprid	0.0800
3e	0.3501	Dinitraz	0.0532
3f	0.4055

苯炔[3+2]环加成反应构建三氟甲基取代的苯并环状亚砜亚胺衍生物及其杀棉蚜活性研究

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

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Entry	F source	Solvent	Temp./℃	Time/h	Yield^b/% of 3a
1	KF/18-C-6	THF	50	20	22
2	KF/18-C-6	CH₃CN	50	20	36
3	KF/18-C-6	Toluene	50	20	11
4	KF/18-C-6	1,4-Dioxane	50	20	12
5	KF/18-C-6	1,2-Dimethoxyethane	50	20	25
6	KF/18-C-6	CH₃CN/toluene (V∶V=4∶1)	50	20	50
7	CsF	CH₃CN/toluene (V∶V=4∶1)	50	20	22
8	KF/18-C-6	CH₃CN/toluene (V∶V=4∶1)	50	11	36
9	KF/18-C-6	CH₃CN/toluene (V∶V=4∶1)	50	36	40
10	KF/18-C-6	CH₃CN/toluene (V∶V=4∶1)	50	48	44
11	KF/18-C-6	CH₃CN/toluene (V∶V=4∶1)	50	96	23
12	KF/18-C-6	CH₃CN/toluene (V∶V=4∶1)	80	11	32
13	KF/18-C-6	CH₃CN/toluene (V∶V=4∶1)	80	23	32
14	KF/18-C-6	CH₃CN/toluene (V∶V=4∶1)	100	9	39
15^c	TBAF	THF	50	22	Nr
16	CsF	CH₂Cl₂	50	12	Nr

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