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Novel benzoylpyrimidylurea compound and preparation and application thereof

A technology of benzoyl pyrimidine urea and compound, which is applied to novel benzoyl pyrimidine urea compounds and the fields of preparation and application thereof, can solve problems such as harm and death of domestic fish, and achieve excellent effect of killing armyworms

Active Publication Date: 2018-11-30
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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  • Novel benzoylpyrimidylurea compound and preparation and application thereof
  • Novel benzoylpyrimidylurea compound and preparation and application thereof
  • Novel benzoylpyrimidylurea compound and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] (1) Preparation of 4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-amine (I-a)

[0060] 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 1molL -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

[0096] (1) Preparation of 4-chloro-6-morpholinopyrimidin-2-amine (I-g)

[0097] 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%.

[0098] 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).

[0099] The intermediates shown in Table 2 below were prepared according to the above method.

[0100] 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 give 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 N ...

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Abstract

The present invention provides a novel benzoylpyrimidylurea compound. The novel benzoylpyrimidylurea compound has a shown structure in a formula I or a formula II. The provided novel benzoylpyrimidylurea compound has excellent armyworm-killing, mosquito-killing and broad-spectrum antifungal activities. Experimental results show that the activity of the provided benzoylpyrimidylurea compound at 0.5[mu]g / mL in killing mosquito larvae can reach 100%; the activity of the benzoylpyrimidylurea compound at 0.25 [mu]g / mL in killing the mosquito larvae can reach 100%; and when the benzoylpyrimidylureacompound is at 50 [mu]g / mL, the benzoylpyrimidylurea compound exhibits the broad spectrum antifungal activity and has a certain protective effect on detached leaves of cabbages. Besides, the benzoylpyrimidylurea compound is low in toxicity of fish; LC50 of zebrafish is 378.387mg / L and 21.668mg / L, respectively. The novel benzoylpyrimidylurea compound can be applied in preparation of a pesticide for killing insects and preventing phytopathogenic 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 in my country 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. However, Zhang Yequn and Zhu Jiaxian reported in 2013 that the Culex pipiens in Huzhou City had 8.96 times the resistance to secbucarb and permethrin, and 5.97 times the resistance to deltamethrin. Jiang Bin, Li Shigen, Quan Xin et al. reported in 2014 that there were dichlorvos-resistant and deltamethrin-resistant Culex pipiens strains in Jining City, and their resistance coef...

Claims

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Application Information

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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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