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Amide-type compound as well as preparation method and application thereof

An amide compound, C1-C6 technology, applied in the field of agricultural insecticides and fungicides

Active Publication Date: 2009-12-09
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Although there are many reports on piperazine and amide compounds, continuous development and research are still needed

Method used

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  • Amide-type compound as well as preparation method and application thereof
  • Amide-type compound as well as preparation method and application thereof
  • Amide-type compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0454] Example 1: Preparation of Table 181-83 Compounds

[0455] (1) Preparation of Intermediate IV-1

[0456]

[0457] Add 9 grams (150 millimoles) of ethylenediamine and 100 milliliters of ethanol successively in a 250 milliliter reaction flask, then slowly drop 22.7 grams (100 millimoles) of 2,3-dichloro-5-trifluoromethylpyridine Add, add dropwise for 30 minutes, and react at room temperature for 2 hours. After the completion of the reaction as monitored by TLC, 22 g of light yellow oil was obtained by desolvation under reduced pressure. Yield 91.7%.

[0458] (2) Preparation of Table 181-83 Compounds

[0459]

[0460] 6-chloro-2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-8-methyl-4H-3,1-benzoxazine- Add 1.00 g (2.21 mmol) of 4-ketone (see WO03015519 for preparation) into a 50 ml reaction flask, add 25 ml of acetonitrile, add 0.53 g of IV-1 (2.21 mmol) while stirring, and react at 40°C for 4 hours. After the completion of the TLC monitoring reaction, desol...

example 2

[0461] Example 2: Preparation of Table 181-287 Compounds

[0462] (1) Preparation of Intermediate IV-2

[0463]

[0464] Add 11.8 g (60 mmol) of piperazine (hexahydrate) into a 150 ml reaction flask containing 40 ml of acetonitrile, raise the temperature to 40°C, and add 2,3-dichloro-5-trifluoromethane dropwise under stirring 10.8 g (50 mmol) of pyridine was added within 15 minutes, then 9 ml of triethylamine was added, and the reaction was maintained at 40° C. for 4 hours. After the reaction was monitored by TLC, it was filtered and washed with a small amount of ethanol to obtain 12 g of a white solid. Yield 90.2%.

[0465] (2) Preparation of Table 181-287 Compounds

[0466]

[0467] 6-chloro-2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-8-methyl-4H-3,1-benzoxazine- Add 1.00 g (2.21 mmol) of 4-ketone (see WO03015519 for preparation) into a 50 ml reaction flask, add 25 ml of acetonitrile, add 0.59 g of IV-2 (2.21 mmol) while stirring, and react at 40°C for 4 h...

example 3

[0473] Example 3: 60% WP

[0474] Table 181-288 Active ingredient 60%

[0475] Sodium dodecyl naphthalene sulfonate 2%

[0476] Sodium lignosulfonate 9%

[0477] Kaolin topped up to 100%

[0478] The components (all solids) were mixed together and pulverized in a pulverizer until the granules were on par.

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Abstract

The invention discloses an amide-type compound as well as a preparation method and an application thereof. The structure of the amide-type compound is shown as a general formula I: each substitutional group is defined as an instruction book. The amide-type compound has broad spectrum insecticidal activity, is very effective to Lepidoptera pests comprising European corn borers, sugarcane borers, codling moths, laspeyresia pomonellas, gypsy moths, rice leaf rollers, corn borers, tobacco leaf moths, small fruit borers, diamond back moths, asparagus caterpillars, prodenia lituras, and the like, and has better activity for the asparagus caterpillars and the prodenia lituras, thereby achieving good effect with low dose. Meanwhile, part of the compound also has good sterilizing activity and can be used for preventing and treating rice blast, tomato late blight, cucumber downy mildew and vegetable gray mold.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides and fungicides, and relates to an amide compound and its preparation and application. Background technique [0002] Early patent US3394137 involves piperazine derivatives shown in the following general formula as insecticides and fungicides: [0003] R 1 is an alkyl or haloalkyl [0004] Patent JP2001354657 relates to piperazine derivatives shown in the following general formula as insecticides and fungicides: [0005] [0006] Patents JP2006188462, US20080076777, CN101128445, US20050032810, and US20030207894 also involve compounds such as piperazines as agricultural chemicals such as fungicides and insecticides. [0007] 专利CN1040029、CN1969853、JP2003335681、US2993062、US5872115、US6313127、US2005119251、US20070027118、US2007004750、US20070190079、US2007219198、WO9728128、WO02102778、WO2004002965、WO2004078732、WO2005023260、WO2006014168、WO2006094843、WO2007009635、WO2007066784、WO2007141039等,有关论文如K...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14A01N43/60A01P7/00A01P3/00
CPCC07D401/14A01N43/60C07D211/04C07D231/10A01N43/56C07D403/12C07D239/24C07D213/74C07D403/14A01N53/00C07D237/06
Inventor 刘长令柴宝山张弘杨吉春李志念彭永武吴峤马士存李淼刘远雄
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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