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Preparation method and application of camphor sulfonyl benzylamine compound

A technology of sulfonylbenzylamine and compound, which is applied in the field of preparation of camphorsulfonylbenzylamine compounds, can solve the problems such as unreported preparation method and sterilization application of camphorsulfonylbenzylamine compound, camphor can not meet the market demand of camphor, and the like, Achieve the effect of novel molecular structure, simple preparation method, and easy availability of raw materials

Active Publication Date: 2022-05-06
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Naturally sourced camphor has been far from meeting the growing market demand for camphor due to lack of resources and protection.
[0005] At present, the preparation method and bactericidal application of camphorsulfonylbenzylamine compounds have not yet been reported

Method used

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  • Preparation method and application of camphor sulfonyl benzylamine compound
  • Preparation method and application of camphor sulfonyl benzylamine compound
  • Preparation method and application of camphor sulfonyl benzylamine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add L-10-camphorsulfonic acid (3.0mmol) and thionyl chloride (3.3mmol) to the single-necked bottle to dissolve, heat up to reflux temperature for 5h, cool, concentrate to remove most of the solvent and HCl, and obtain white solid L-10 -camphorsulfonyl chloride, the product was directly put into the next step without further treatment.

[0033]

[0034] Dissolve 2,4-difluorobenzylamine (1.0mmol), 4-dimethylaminopyridine (0.1mmol), and triethylamine (1.1mmol) in anhydrous dichloromethane, cool to 0°C, and add L -10-Camphorsulfonyl chloride (1.10mol), raised to 25°C for 3h. The complete reaction of raw materials was monitored by TLC. The organic layer was washed 3 times with water (8ml×3), washed 3 times with saturated brine (8mL×3), dried, filtered with suction, concentrated to remove dichloromethane, and the crude product was subjected to column chromatography (CH 2 Cl 2 :MeOH=20:1) to obtain target compound I-1, white solid, m.p.52-54 ℃, yield 85%. 1 H NMR (600MHz...

Embodiment 2

[0036]

[0037] Dissolve 3-chlorobenzylamine (1.0mmol), 4-dimethylaminopyridine (0.1mmol), and triethylamine (1.1mmol) in anhydrous dichloromethane, cool to 0°C, and add L-10- Camphorsulfonyl chloride (1.10mol) was raised to 25°C for 5h. The complete reaction of raw materials was monitored by TLC. The organic layer was washed 3 times with water (8ml×3), washed 3 times with saturated brine (8mL×3), dried, filtered with suction, concentrated to remove dichloromethane, and the crude product was subjected to column chromatography (CH 2 Cl 2 :MeOH=20:1) to obtain target compound I-2, colorless oil, yield 80%. 1 H NMR (600MHz, CDCl 3)δ7.38(s,1H),7.28–7.27(m,3H),5.88(s,1H),4.37–4.29(m,2H),3.18(d,J=15.1Hz,1H),2.89(d ,J=15.1Hz,1H),2.39–2.35(m,1H),2.17–2.10(m,2H),2.04–1.90(m,3H),1.45–1.40(m,1H),0.96(s,3H) ),0.79(s,3H). 13 C NMR (150MHz, CDCl 3 )δ217.18, 139.11, 134.49, 129.95, 128.26, 127.92, 126.34, 59.27, 50.69, 48.79, 47.05, 42.91, 42.68, 26.94, 26.85, 19.71, 19.30.

Embodiment 3

[0039]

[0040] Dissolve 2-chloro-4-fluorobenzylamine (1.0mmol), 4-dimethylaminopyridine (0.1mmol), and triethylamine (1.1mmol) in anhydrous dichloromethane, cool to 0°C, and add in batches L-10-camphorsulfonyl chloride (1.10mol), raised to 25°C for 4.5h. The complete reaction of raw materials was monitored by TLC. The organic layer was washed 3 times with water (8ml×3), washed 3 times with saturated brine (8mL×3), dried, filtered with suction, concentrated to remove dichloromethane, and the crude product was subjected to column chromatography (CH 2 Cl 2 :MeOH=20:1) to obtain target compound I-3, white solid, m.p.106-107.5°C, yield 83%. 1 H NMR (600MHz, CDCl 3 )δ7.54(dd, J=8.5,6.0Hz,1H),7.16(dd,J=8.4,2.6Hz,1H),7.04–7.01(m,1H),5.91–5.89(m,1H),4.49 –4.42(m,2H),3.21(d,J=15.1Hz,1H),3.00–2.86(m,1H),2.42–2.38(m,1H),2.20–2.13(s,2H),2.06–2.00 (m,2H),1.94(d,J=18.6Hz,1H),1.49–1.43(m,1H),1.00(s,3H),0.83(s,3H). 13 C NMR (150MHz, CDCl 3 )δ216.72, 161.98(d, J=248.8Hz), 134.22(d, J=...

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Abstract

The invention discloses a preparation method and application of a camphor sulfonyl benzylamine compound, the structural formula of the camphor sulfonyl benzylamine compound is shown in the specification, and the camphor sulfonyl benzylamine compound is applied to prevention and treatment of plant fungi in agriculture or forestry. Activity results show that the compound has a good control effect on sclerotinia sclerotiorum and rhizoctonia solani.

Description

technical field [0001] The invention belongs to the technical field of pesticide synthesis, and in particular relates to a preparation method and application of camphorsulfonylbenzylamine compounds. Background technique [0002] Sulfonamide compounds have a wide range of biological activities in medicine and pesticides, such as: sterilization, herbicide, insecticide, anticancer, antidiabetic, etc. In recent years, there have been many studies on sulfonamide compounds, and high-efficiency and low-toxicity fungicides such as sulfamethanil and sulfamethanil have been developed successively; a large number of sulfonamide compounds with anti-tumor activity have been reported, some of which have entered the clinical trial stage. [0003] On the other hand, the research of terpenoids in medical or agricultural fields has attracted extensive attention. As an important forest resource, camphor is a non-woody forest product with a bicyclic monoterpene structure, which naturally exist...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/10C07C303/38C07D213/61A01N41/06A01N47/02A01N43/40A01P3/00
CPCC07C311/10C07C303/38C07D213/61A01N41/06A01N43/40C07C2602/42
Inventor 谷文杨子辉王石发孙雪宝孙露陈霖霖
Owner NANJING FORESTRY UNIV
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