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Substituted p-trifluoromethyl phenyl ether compound and its prepn and application

A technology of trifluoromethyl phenyl ether and compounds, which is applied in the field of substituted p-trifluoromethyl phenyl ether compounds, and can solve the problems that trifluoromethyl phenyl ether compounds are not specifically disclosed.

Active Publication Date: 2007-01-03
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although there are many patents and commercialized varieties, although the compound of the present invention may be included in the large protection scope of the existing patent, the substituted p-trifluoromethylphenyl ether compounds involved in the present invention are not specifically disclosed

Method used

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  • Substituted p-trifluoromethyl phenyl ether compound and its prepn and application
  • Substituted p-trifluoromethyl phenyl ether compound and its prepn and application
  • Substituted p-trifluoromethyl phenyl ether compound and its prepn and application

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0063] Example 1: Preparation of Compound 1

[0064]

[0065] At room temperature, the mixture containing 0.8 g of anhydrous potassium carbonate, 0.39 g of (II-1), 0.4 g of (III-1) in 20 ml of N,N-dimethylformamide was heated under reflux and stirred for 5 hours, and the The reaction mixture was poured into ice water, extracted three times with ethyl acetate, the combined extracts were washed three times with saturated brine, dried, filtered, and concentrated under reduced pressure to obtain a light yellow solid as a crude product. Column chromatography with a mixture of ethyl acetate and petroleum ether (1:8) gave 0.51 g of the title compound, melting at 104-106°C. Yield 70.5%.

[0066] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0067] δppm 3.71(3H, s), 3.83(3H, s), 5.12(2H, s), 6.89(1H, d), 7.20(1H, t), 7.35(3H, m), 7.53(1H, m), 7.62 (2H, s).

example 2

[0068] Example 2: Preparation of Compound 4

[0069]

[0070] At room temperature, the mixture containing 0.8 g of anhydrous potassium carbonate, 0.39 g of (II-1), 0.42 g of (III-2) in 20 ml of N,N-dimethylformamide was heated under reflux and stirred for 5 hours, and the The reaction mixture was poured into ice water, extracted three times with ethyl acetate, the combined extracts were washed three times with saturated brine, dried, filtered, and concentrated under reduced pressure to obtain a light yellow solid as a crude product. Column chromatography with a mixture of ethyl acetate and petroleum ether (1:8) gave 0.53 g of the title compound with a melting point of 115-116°C. Yield 73.2%.

[0071] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0072] δppm 3.88(3H, s), 4.04(3H, s), 5.09(2H, s), 6.93(1H, d), 7.22(1H, d), 7.45(3H, m), 7.58(1H, d), 7.63 (1H, s).

example 3

[0073] Example 3: Preparation of Compound 7

[0074]

[0075] 0.60 g of compound 4 and an aqueous solution of methylamine with twice the molar ratio were stirred overnight at room temperature in 50 ml of tetrahydrofuran, concentrated and then extracted twice with ethyl acetate. The combined extracts were washed with water for three times and then washed twice with saturated brine. After drying, filtration and concentration, 0.53 g of the title compound was obtained, with a melting point of 92-94°C. Yield 88.5%.

[0076] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0077] δppm 2.92(3H, s), 3.92(3H, s), 5.12(2H, s), 6.95(1H, d), 7.24(1H, m), 7.42(3H, m), 7.54(1H, d), 7.62 (1H, s).

[0078] Other compounds were synthesized according to the above method.

[0079]The NMR data of the general formula I compound shown in part table 1 ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0080] Compound 10: oily substance....

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Abstract

The present invention belongs to the field of farm pesticide and germicide technology, and is especially one kind of substituted p-trifluoromethyl phenyl ether compound and its preparation and application. The substituted p-trifluoromethyl phenyl ether compound has the general expression as shown. It has broad spectrum germicidal activity of preventing and controlling powdery mildew, grape downy mildew, sheath and culm blight of rice and other diseases, and high pesticidal activity of preventing and controlling carminespider mite, armyworm, cabbage moth and other pests to crops.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides and fungicides, and in particular relates to a substituted p-trifluoromethylphenyl ether compound and its preparation and application. Background technique [0002] Since the fluorine atom has special properties such as good simulation effect, electronic effect, hindrance effect and penetration effect, its introduction can double the activity of the compound. In recent years, new varieties of fluorine-containing pesticides have emerged continuously, accounting for an increasing proportion of new pesticide varieties. [0003] Methoxyacrylate compounds are known biologically active compounds. There are many reported patents such as EP335519, US4829085, US4914128, US5145980, US5157144, US5334748, US5395854, US6653258, US2004029944, WO2003087032, etc. There are also many known commercial varieties, and the structures and names of some commercial varieties are as follows: [0004] [0005]...

Claims

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Application Information

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IPC IPC(8): C07C69/54C07C229/30C07C237/16C07D273/00C07D239/34A01N37/06A01N37/44A01N43/72A01N43/54
CPCA01N37/36C07D239/52C07C69/736A01N47/24A01N43/88A01N37/50C07C255/54A01N43/54C07C67/31C07C271/28C07D413/12C07C251/48
Inventor 刘长令迟会伟崔东亮李淼李志念罗艳梅
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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