Substituted aryl ethers compounds as well as preparation and uses thereof

A technology of compounds and aryl ethers, applied in the fields of agricultural insecticides and fungicides, can solve the problems that substituted aryl ether compounds are not specifically disclosed, etc.

Active Publication Date: 2011-04-27
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 structures, the substituted aryl ether compounds involved in the present invention are not specifically disclosed

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

[0151] Example 1: Preparation of compound 40

[0152]

[0153] At room temperature, the 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 under reflux and stirred for reaction 5 After hours, the reaction mixture was poured into ice water, extracted with ethyl acetate 3 times, the extracts were combined, washed with saturated brine 3 times, 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) yielded 0.51 g of the title compound, melting point 84-86°C. The yield was 70.5%.

[0154] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0155] 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

[0156] Example 2: Preparation of compound 193

[0157]

[0158] 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. , Pour the reaction mixture into ice water, extract 3 times with ethyl acetate, combine the extracts, wash 3 times with saturated brine, dry, filter, and concentrate under reduced pressure to obtain a pale yellow solid as a crude product. Column chromatography with a mixture of ethyl acetate and petroleum ether (1:8) gave the title compound 0.53 g, melting point 92-94°C. The yield was 73.2%.

[0159] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0160] 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

[0161] Example 3: Preparation of Compound 323

[0162]

[0163] 0.60 g of compound 193 was stirred in 50 ml of tetrahydrofuran at room temperature with twice the molar ratio of methylamine aqueous solution overnight, concentrated and then extracted with ethyl acetate twice, the combined extracts were washed with water three times, and then with saturated brine twice. Dry, filter, and concentrate to obtain 0.53 g of the title compound, melting point 132-134°C. The yield was 88.5%.

[0164] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0165] 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).

[0166] Other compounds of the present invention can be synthesized by referring to the above methods.

[0167] Part of the nuclear magnetic data of the compounds of general formula I shown in Table 1 and Table 2 ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0168] Compound 6...

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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), wherein Ar represents Ar-1 or Ar-2. 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 specifically relates to substituted aryl ether compounds and their preparation and application. Background technique [0002] Methoxyacrylate compounds are known compounds with biological activity. There are many patents and documents reported, such as CN1030749A, CN1188394A, EP335519A, US4829085, US4914128, US5145980, US5157144, US5334748, US5395854, US5548078, US2004029944A, WO9515083A, WO9517818A, WO9823155A, WO9823156A, WO2003087032A, WO2003087032A, WO2003087032A; , 11343-11364; Nippon Noyaku Gakkaishi (1998), 23(2), 107-112; Shionogi Kenkyusho Nenpo (1997), 47, 33-57, etc. [0003] There are also many known commercial varieties. The structure and names of some commercial varieties are as follows: [0004] [0005] The applicant of the present invention discloses a compound of the following general formula in the Chinese patent application titled "Substituted p-trifluorome...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D273/01C07C69/734C07C251/48C07C271/28A01N37/44A01N37/52A01P3/00A01P5/00A01P7/00
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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