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A kind of benzoyl pyrimidine urea compound and its preparation and application

A compound, pyrimidine urea technology, applied in the field of new benzoyl pyrimidine urea compounds and their preparation and application, can solve the problems of death, domestic fish hazards, etc., and achieve excellent armyworm killing and broad-spectrum antifungal activity

Active Publication Date: 2021-06-15
HAINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, the current pesticides will cause different degrees of harm to domestic fish, and even cause death

Method used

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  • A kind of benzoyl pyrimidine urea compound and its preparation and application
  • A kind of benzoyl pyrimidine urea compound and its preparation and application
  • A kind of benzoyl pyrimidine urea compound and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] (1) Preparation of 4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-amine (I-a)

[0061] Under the protection of inert gas, add 12mL of dry THF to a 100mL three-neck flask containing sodium hydride (0.35g, 14.6mmol), and slowly add 2,2,2-trifluoroethanol dropwise when the temperature of the reaction system drops to 0°C (1.5 g, 15.2 mmol). When the reaction system stopped emitting gas and the reaction solution became clear, 2-amino-4,6-dichloropyrimidine (1.0 g, 6.1 mmol) was added into the three-necked flask. The temperature of the reaction system was raised to 62° C. for 15 h, and the reaction was monitored by TLC until the reaction was complete. Stop heating, cool the reaction system to room temperature, add 1mol L -1 hydrochloric acid solution to quench the reaction. Extract with ethyl acetate, separate the organic phase, wash the organic phase twice with sodium bicarbonate solution, and dry over anhydrous magnesium sulfate. After filtration, the filtrate was spin-dried...

Embodiment 2

[0097] (1) Preparation of 4-chloro-6-morpholinopyrimidin-2-amine (I-g)

[0098] Add cuprous iodide (5.8mg, 0.031mmol), potassium carbonate (0.41g, 2.9mmol), morpholine (0.21g, 2.4mmol) and 2-amino-4, 6-Dichloropyrimidine (0.40g, 2.4mmol) was first stirred at room temperature for 30min, then the reaction system was heated to 110°C, and the reaction was monitored by TLC. After the reaction was completed, the reaction system was cooled to room temperature, washed with water, extracted with ethyl acetate, and the organic phase was dried with anhydrous magnesium sulfate. The solvent was spun off under reduced pressure and passed through a silica gel column to obtain a white solid with a yield of 79.1%.

[0099] mp 210-212°C. 1 H NMR(500MHz,Chloroform-d)δ5.94(s,1H,ArH),5.00(s,2H,NH 2 ),3.79–3.68(m,4H,morpholine),3.55(t,J=4.9Hz,4H,morpholine).

[0100] The intermediates shown in Table 2 below were prepared according to the above method.

[0101] Table 2 Structure and Characteriz...

Embodiment 3

[0120] (1) Preparation of N-((4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)thiocarbamoyl)-2-chlorobenzamide (31)

[0121] 2-Chlorobenzoyl isothiocyanate (988 mg, 5 mmol), compound I-a (1.4 g, 5 mmol) and NBS (10 mol%) were mixed and dissolved in 5 mL of anhydrous MeCN. The reaction was then heated to reflux for 4 hours. When the reaction was complete, it was cooled to room temperature, diluted with 20 mL of EtOAc, washed twice with brine (20 mL), washed with anhydrous Na 2 SO 4 Dry and evaporate in vacuo. Finally, the residue was purified by silica gel column chromatography to afford compound 31 as a yellow solid in 53% yield, mp 93-95°C. 1 H NMR (500MHz, DMSO-d 6 )δ12.84(s,1H,NH),12.45(s,1H,NH),7.71–7.62(m,1H,Ph),7.56(dd,J=6.5,1.7Hz,2H,Ph),7.51– 7.42(m,1H,Ph),6.51(s,1H,ArH),5.11(q,J=8.9Hz,4H,OC H 2 CF 3 ). 13 CNMR (126MHz, DMSO) δ178.26, 170.77, 168.24, 156.18, 135.15, 133.26, 131.05, 130.65, 130.34, 128.15, 125.61, 88.16, 63.87, 63.59, 63.32, 63.04. 16 h 11 CIF 6...

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Abstract

The invention provides a benzoyl pyrimidine urea compound, which has the structure shown in formula I or formula II. The benzoyl pyrimidine urea compounds provided by the invention have excellent anti-mygicide, anti-mosquito and broad-spectrum antifungal activities. Experimental result shows, the benzoyl pyrimidine urea compound provided by the invention is in 0.5 μ g mL ‑1 The mosquito larval killing activity can reach 100%, at 0.25μg mL ‑1 The activity of killing mosquito larvae can reach 100%. at 50 μg mL ‑1 It exhibited broad-spectrum antifungal activity and had a certain protective effect on the detached leaves of cabbage. And low toxicity to fish, the LC of zebrafish 50 Respectively 378.387mg L ‑1 , 21.668 mg L ‑1 . It can be used for preparing pesticides for killing insects and resisting plant pathogenic fungi.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a novel benzoyl pyrimidine urea compound and its preparation and application. Background technique [0002] Culex pipiens pallens is a harassing domestic dominant mosquito species and an important vector of epidemic Japanese encephalitis (JE), Bancroft's filariasis and West Nile virus. Currently commonly used high-efficiency insecticides are the following: pyrethroids, such as beta-cypermethrin, permethrin, deltamethrin; organophosphorus, such as dichlorvos; carbamates, such as secbucarb. At present, there is a risk of drug resistance to the commonly used insecticides on the market, and the development of new insecticides is imminent. [0003] CN102690241A discloses the preparation and insecticidal activity of benzoylurea compounds containing isoxazoline and isoxazole structures, and CN101602695A discloses the preparation and insecticidal activity of benzoylurea compounds con...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/52C07D239/48C07D239/42C07D239/47C07D403/12C07D401/12A01N47/36A01P7/04A01P3/00
CPCA01N47/36C07D239/42C07D239/47C07D239/48C07D239/52C07D401/12C07D403/12
Inventor 孙然锋陈佩琦宋祥民范咏梅
Owner HAINAN UNIVERSITY
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