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Pyrimidylsalicylate type compounds, and preparing method and applications thereof

A technology for pyrimidine salicylic acids and compounds, which is applied in the field of pyrimidine salicylic acids and their preparation, and achieves the effect of effective prevention and treatment

Inactive Publication Date: 2014-11-12
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to long-term use, the problem of weed resistance to herbicides has also emerged

Method used

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  • Pyrimidylsalicylate type compounds, and preparing method and applications thereof
  • Pyrimidylsalicylate type compounds, and preparing method and applications thereof
  • Pyrimidylsalicylate type compounds, and preparing method and applications thereof

Examples

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preparation example Construction

[0040] In a second aspect, the present invention provides a method for preparing pyrimidine salicylic acid compounds represented by formula (I), the method comprising the following steps:

[0041] (1) Dissolving the compound represented by formula (II) in an organic solvent, and then contacting it with a basic inorganic salt, so that the hydrogen on the hydroxyl group in the compound of formula (II) is replaced;

[0042] (2) The product obtained in step (1) is contacted with the pyrimidine compound represented by formula (III) to carry out nucleophilic substitution reaction, and the aqueous solution of the solid product obtained by the reaction is acidified to a pH of 0-1 to obtain formula (I) The indicated pyrimidine salicylates;

[0043] Formula (I)

[0044] Formula (II)

[0045] Formula (III)

[0046] in,

[0047] R 1 is methyl or trifluoromethyl;

[0048] R 2 At least one selected from hydrogen, methyl, halogen, nitro, methoxy and trifluoromethyl, n is 0, 1, 2...

Embodiment 1

[0075] This example is used to illustrate the pyrimidine salicylate compound of the present invention and its preparation method.

[0076] Dissolve 1mmol of compound A in 30mL of redistilled toluene, add 2mmol of potassium carbonate, react at 20°C for 2 hours, then add 4,6-dimethoxy-2-thiamphenicol pyrimidine (1mmol), at 120°C Under reaction 12h. The solvent was distilled off under reduced pressure, a small amount of water was added to dissolve the solid completely, the aqueous layer was washed several times with ether, the aqueous layer was acidified to pH=1 with concentrated hydrochloric acid, extracted with dichloromethane, dried over anhydrous sodium sulfate, and pyrimidine salicyl was obtained by column chromatography Acid compound A1. The yield of Compound A1 prepared from Compound A was 78%. A1(Y11149):mp:144-145℃. 1 H NMR(600MHz,dmso)δ12.83(s,1H),7.45–7.40(m,4H),7.38(d,J=6.6Hz,1H),7.15(s,1H),7.13(s,1H) ,6.00(s,1H),3.79(s,6H),2.39(s,3H).HRMS(MALDI):Calcd for C 20 h...

Embodiment 2

[0079] This example is used to illustrate the pyrimidine salicylate compound of the present invention and its preparation method.

[0080] Dissolve 1mmol of compound B in 30mL of redistilled toluene, add 2mmol of potassium carbonate, react at 23°C for 1.5 hours, then add 4,6-dimethoxy-2-thiamphenicol pyrimidine (1mmol), at 118°C Under reaction 16h. The solvent was distilled off under reduced pressure, a small amount of water was added to dissolve the solid completely, the aqueous layer was washed several times with ether, the aqueous layer was acidified to pH=1 with concentrated hydrochloric acid, extracted with dichloromethane, dried over anhydrous sodium sulfate, and pyrimidine salicyl was obtained by column chromatography Acid compound B1. The yield of Compound B1 prepared from Compound B was 65%. B1(Y11150):mp:140-141℃. 1 H NMR(600MHz,dmso)δ12.99(s,1H),7.48(d,J=7.2Hz,1H),7.33–7.08(m,5H),6.02(s,1H),3.79(s,6H) ,2.39(s,3H).HRMS(MALDI):Calcd for C 20 h 17 FN 2 o 5 [M+H...

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Abstract

Pyrimidylsalicylate type compounds are disclosed. The compounds are characterized in that: the structure of the compounds is shown as a formula (I), wherein R1 is methyl or trifluoromethyl, R2 is at least one selected from hydrogen, methyl, halogen, nitro, methoxyl and trifluoromethyl, and n is 0, 1, 2, 3, 4, or 5. A preparing method of the compounds and applications of the compounds in weed control are also provided. The compounds are high in activity and anti-resistance property, effectively control resistant weeds, and particularly have good effects for control of flixweed, ammannia arenaria, and other intractable resistant weeds. The formula (I) is shown in the specification.

Description

technical field [0001] The invention relates to a class of pyrimidine salicylic acid compounds and a preparation method thereof, as well as the application of the pyrimidine salicylic acid compounds in controlling weeds. Background technique [0002] Weeds are a major hazard in agriculture and forestry. Weeds compete with crops for nutrients, water, sunlight and space, hinder the ventilation and light transmission of the field, and increase the local climate temperature. Some weeds are intermediate hosts of diseases and insect pests, which promote the occurrence of diseases and insect pests; Reduce crop yield and quality. In addition, the seeds or pollen of some weeds contain toxins, which can poison humans and animals. Therefore, herbicides are called the hot spot of pesticide chemistry research. [0003] At present, there are many kinds of herbicides, mainly sulfonylureas, sulfonamide triazolones, imidazolinones, triazolopyrimidines, pyrimidine thiobenzoates, etc. Howe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/60A01N43/54A01P13/00
CPCA01N43/54C07D239/60
Inventor 杨光富刘玉超陈琼陈杰崔海兰唐伟
Owner HUAZHONG NORMAL UNIV
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