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O-formammidotiazol-benzamide compounds and use thereof

A technology of o-formamidobenzamide and compounds, which is applied in the field of o-formamidobenzamide compounds, and can solve the problems of no bactericidal activity and different structures of compounds

Active Publication Date: 2012-02-15
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 all disclosed compounds in the above patents (applications) have similarities with the compounds of the present invention, there are still significant differences in their structures, and there are no reports of bactericidal activity in the compounds involved in the literature

Method used

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  • O-formammidotiazol-benzamide compounds and use thereof
  • O-formammidotiazol-benzamide compounds and use thereof
  • O-formammidotiazol-benzamide compounds and use thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0194] Example 1: Preparation of Compound 1-12

[0195]

[0196] Take 0.23 g of sodium hydride in a 100 ml reaction bottle, wash twice with petroleum ether, add 40 ml of tetrahydrofuran, add NH 2 CN, react until no bubbles are released, then raise the temperature to 35°C for 10 minutes, add 0.5 g of II-I (see WO03015519 for preparation), and stir for 3 hours. After the completion of the TLC monitoring reaction, after desolvation under reduced pressure, pour 50 milliliters of saturated saline into the reaction flask, extract three times with 60 milliliters of ethyl acetate, dry, desolventize, and obtain 0.45 grams of the product by column chromatography, namely the compound 1-12. Yield 82.4%.

example 2

[0197] Example 2: Preparation of Compound 1-99

[0198]

[0199] Take 0.5 g of II-I in a 50 ml reaction flask, add 25 ml of acetonitrile, and add 0.3 g of NH 2 C(CH 3 )=CHCN, the temperature was raised to reflux for 8 hours. After TLC monitors the completion of the reaction, after desolvation under reduced pressure, pour 50 milliliters of saturated saline into the reaction flask, extract three times with 60 milliliters of ethyl acetate, dry, and desolventize, and obtain 0.39 grams of product by column chromatography, namely compound 1-99. Yield 66.1%.

example 3

[0200] Example 3: Preparation of Compound 2-4

[0201]

[0202] Take 0.5 g of II-I in a 50 ml reaction flask, add 25 ml of acetonitrile, add 0.03 g of ethylenediamine under stirring, and heat up and reflux for 15 hours. After TLC monitors the completion of the reaction, after desolvation under reduced pressure, pour 50 milliliters of saturated saline into the reaction flask, extract three times with 60 milliliters of ethyl acetate, dry, and desolventize, and column chromatography gives 0.19 grams of the product, namely compound 2-4. Yield 39.6%.

[0203] Other compounds of general formula I can be prepared by the preparation methods provided by the present invention.

[0204] NMR data of some compounds ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0205] Compound 1-12: melting point 118-120°C. δppm 2.08(3H, s), 7.34(1H, s), 7.37(1H, s), 7.63(1H, q), 7.70(1H, s), 8.02(1H, s), 8.19(1H, m), 8.52 (1H, m), 11.71 (1H, s).

[0206] Compound 1-93: m...

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PUM

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Abstract

The invention discloses anthranilic diamide compounds and application thereof; the structures of the compounds are showed by a general formula I; the definitions of each substitutional group are seen in an instruction; the anthranilic diamide compounds of the invention have broad-spectrum insecticidal activity and is very effective to lepidopterous pests which include European corn borers, sugarcane borers, codling moths, lessorapple-worms and gypsy moths; the activity is especially better to diamond back moths; better effect can be obtained under low dosage. Simultaneously, a part of the compounds also have better sterilizing activity and can be used for controlling rice blasts, cucumber downy mildews and anthraxes.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides and fungicides. Specifically, it relates to a kind of o-formamidobenzamide compound and application thereof. Background technique [0002] O-formamidobenzamide compounds (ryanodine receptors) are effective insecticides developed in recent years to control Lepidoptera pests. [0003] Patent WO2001070671 discloses the following compounds with insecticidal activity: [0004] [0005] Patent WO03015519 discloses the following compounds with insecticidal activity: [0006] [0007] Patent WO2004033468 discloses the following compounds with insecticidal activity: [0008] [0009] Patent WO2004067528 discloses the following compounds with insecticidal activity: [0010] [0011] Although all the compounds disclosed in the above patents (applications) have similarities with the compounds of the present invention, there are still significant differences in their structures, and the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/14C07D231/16C07D401/04C07D401/14A01N43/56A01P5/00A01P7/00A01P3/00
Inventor 刘长令柴宝山袁静杨吉春张弘李淼李志念迟会伟
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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