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Compound of 1-pyrimidine ketone group-4-chlorine-5-benzoic ethers and preparation method thereof

A technology of ester compound and pyrimidinone group, which is applied in the field of 1-pyrimidinone-4-chloro-5-benzoic acid ester compound and its preparation, can solve the problem of 1-pyrimidinone-4-chloro-5- 5-Benzoic acid monosubstituted methyl ester compounds and other issues

Inactive Publication Date: 2005-10-26
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] EP195346A2, US4943309 and US 6207830 disclose the synthesis and herbicidal activity of some 1-pyrimidinone-4-chloro-5-benzoate compounds, but none of the prior art relates to 1-pyrimidinone as shown in the present invention 4-Chloro-5-benzoic acid monosubstituted methyl esters

Method used

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  • Compound of 1-pyrimidine ketone group-4-chlorine-5-benzoic ethers and preparation method thereof
  • Compound of 1-pyrimidine ketone group-4-chlorine-5-benzoic ethers and preparation method thereof
  • Compound of 1-pyrimidine ketone group-4-chlorine-5-benzoic ethers and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of Compounds (II-3)~(II-7)

[0034]

[0035] Step 1: Add 30mmol of compound (II-2), 30-36mmol of ethyl trifluoroacetoacetate (II-1) and 250mL of toluene into a 500mL three-neck flask, install a stirring and distillation device, stir and heat slowly at 10°C At the same time, the toluene in the reaction solution and the ethanol generated were distilled out, an average of 20 mL per hour; after the reaction was carried out for 1 hour, 3 mmol of ethyl trifluoroacetoacetate (II-1) was added to continue the reaction, and then added after 2 hours Ethyl trifluoroacetoacetate (II-1) 3mmol and toluene 40mL, stop the reaction after 4 hours. The reaction solution was concentrated and purified by silica gel column chromatography, the developing solvent was ethyl acetate / n-hexane=1 / 5 to obtain 15 mmol of waxy solid (II-3) with a yield of 50%. 1 H NMR (CDCl 3 , 300MHz): δ5.260(s, 1H), 5.346(s, 2H), 7.425(m, 6H), 7.747(m, 1H), 7.898(s, 1H).

[0036] Step 2: Add (II-3) 15...

Embodiment 2

[0041] R=CH in the compound general formula (I) of the present invention listed in table 1 3 -Synthesis:

[0042]

[0043] 0.5 mmol of compound (II-7) prepared in Example 1, 1 mmol of ethyl iodide, 0.6 mmol of potassium carbonate and 10 mL of DMF were added to a 20 mL three-necked flask and stirred at 65° C. for 3 hours. The residue was poured into 10 ml of water, extracted twice with ethyl acetate, 20 ml each time, washed with 15 ml of saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was passed through a silica gel column. Purified by chromatography, the eluent was ethyl acetate / n-hexane=1 / 3, and the compound (I)-1 in Table 1 was obtained as a white solid 0.33 mmol, the yield was 66%, and the melting point was 101-102°C. Replace the solvent DMF with chloroform, dichloromethane, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetone, THF or dioxane, and replace the base ...

Embodiment 3

[0045] The compounds of the present invention listed in Table 1 have the general formula (I) formula R=CH 3 CH 2 -Synthesis:

[0046] Except that iodoethane was replaced by iodopropane, other operating procedures were the same as in Example 2, and compound (I)-2 in Table 1 was obtained as a white solid, melting point: 98-99°C.

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Abstract

The present invention relates to a 1-pyrimidone group-4-chlo-5-benzoate compound and its preparation method. Said invention also provides the general formula of said compound. Said compound can be used as weedicide, and has high herbicidal activity.

Description

technical field [0001] The technical scheme of the present invention relates to heterocyclic compounds containing 1,3-diazine rings that are not fused with other rings, specifically a 1-pyrimidinone-4-chloro-5-benzoate compound and its preparation method. Background technique [0002] Due to the succession and change of weed populations and the emergence and rapid development of resistance to chemical pesticides; the strengthening of people's awareness of ecological environment protection and the awareness of chemical pesticide pollution, the impact of pesticides on non-target organisms, and the fate of pesticides in the ecological environment Pay attention to; the reduction of the world's cultivated land area and the increase in the demand for food due to population growth; the rapid development of agricultural production technology and the continuous improvement of farming systems, etc., need to continuously invent new and improved herbicidal compounds and compositions. ...

Claims

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Application Information

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IPC IPC(8): C07D239/46
Inventor 李斌杨华铮刘斌胡方中邹小毛
Owner NANKAI UNIV
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