Substituted aryl ethers compounds as well as preparation and uses thereof

A technology of compound and aryl ether, which is applied in the field of agricultural insecticide and fungicide, can solve the problem that substituted aryl ether compounds are not disclosed in detail

Active Publication Date: 2008-06-25
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Although there are many patents and commercialized varieties of compounds with similar struct...

Method used

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  • Substituted aryl ethers compounds as well as preparation and uses thereof
  • Substituted aryl ethers compounds as well as preparation and uses thereof
  • Substituted aryl ethers compounds as well as preparation and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0131] Example 1: Preparation of Compound 40

[0132]

[0133] At room temperature, a mixture containing 0.8 g of anhydrous potassium carbonate, 0.39 g of compound (II-1), and 0.4 g of compound (III-1) in 20 ml of N,N-dimethylformamide was heated to reflux and stirred for reaction 5 After 2 hours, the reaction mixture was poured into ice water, extracted 3 times with ethyl acetate, the combined extracts were washed 3 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 with a melting point of 84-86°C. Yield 70.5%.

[0134] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0135] δppm 3.71(3H, s), 3.84(3H, s), 5.10(2H, s), 7.01(1H, m), 7.20(1H, m), 7.25(1H, m), 7.35(2H, m), 7.56 (1H, m), 7.62 (1H, s).

example 2

[0136] Example 2: Preparation of compound 193

[0137]

[0138] At room temperature, the mixture containing 0.8 g of anhydrous potassium carbonate, 0.39 g of compound (II-2), 0.42 g of compound (III-2) in 20 ml of N,N-dimethylformamide was heated under reflux and stirred for 5 hours , 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, melting at 92-94°C. Yield 73.2%.

[0139] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0140] δppm 3.86(3H, s), 4.04(3H, s), 5.06(2H, s), 7.06(1H, d), 7.15(1H, m), 7.23(1H, m), 7.44(3H, m), 7.58 (1H, m).

example 3

[0141] Example 3: Preparation of compound 323

[0142]

[0143] 0.60 g of compound 193 and an aqueous solution of twice the molar ratio of methylamine 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 132-134°C. Yield 88.5%.

[0144] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0145]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).

[0146] Other compounds of the present invention can be synthesized with reference to the above methods.

[0147] The NMR data of the general formula I compound shown in part table 1 and table 2 ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )a...

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Abstract

The invention belongs to the field of the agricultural pesticides and fungicides, in particular discloses a replaced aryl ether compounds and the preparation and application. The replaced aryl ether compounds of the invention are shown as the general formula (I): the general formula (I) compounds of the invention have the broad-spectrum activity--the compounds have very favorable control effects on the diseases such as the grape downy mildew, rice sheath blight, rice-blast disease, tomato late blight, powdery mildew, cucumber powdery mildew, cucumber downy mildew, cucumber gray mold, etc. The compounds of the invention simultaneously have very good insecticidal activity, have effects on a plurality of pests such as the armyworm, the diamondback moth, etc. and are very suitable for the integrated control of the pests on various crops.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides and fungicides, and in particular relates to substituted aryl ether compounds and their preparation and application. Background technique [0002] Methoxyacrylate compounds are known biologically active compounds. 报道的专利和文献很多如CN1030749A、CN1188394A、EP335519A、US4829085、US4914128、US5145980、US5157144、US5334748、US5395854、US5548078、US2004029944A、WO9515083A、WO9517818A、WO9823155A、WO9823156A、WO9703950A、WO2003087032A;Tetrahedron(1999),55(37) , 11343-11364; Nippon Noyaku Gakkaishi (1998), 23(2), 107-112; Shionogi Kenkyusho Nenpo (1997), 47, 33-57 et al. [0003] There are also many known commercial varieties, and the structure and names of some commercial varieties are as follows: [0004] [0005] The applicant of the present invention disclosed the compound of the following general formula in the Chinese patent application titled "Substituted p-trifluoromethylphenyl ether compounds and their pre...

Claims

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Application Information

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IPC IPC(8): C07C69/734C07C251/48C07C271/28C07D273/01A01N37/44A01N37/52A01P3/00A01P5/00A01P7/00
Inventor 刘长令迟会伟李淼李志念柴宝山崔东亮李洋袁静张弘杨吉春刘远雄王立增
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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