Anthranilic acid compound and use thereof

An anthranilic acid and compound technology, applied to N-oxides, anthranilic acid compounds, salts and compositions, as the application field of pesticides, can solve problems such as increased consumer spending and reduced productivity

Active Publication Date: 2012-11-07
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Invertebrate pest damage to growing and stored crops can cause significant reductions in productivity and consequently increased costs to consumers
Many products are commercially available for these purposes, but there is still a need for new compounds that are more effective, low cost, less toxic, environmentally safe, or have a different mode of action

Method used

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  • Anthranilic acid compound and use thereof
  • Anthranilic acid compound and use thereof
  • Anthranilic acid compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0121] Example 1: Preparation of compound 1-152

[0122]

[0123] Take 0.5 g of II-I in a 50 ml reaction flask, add 25 ml of tetrahydrofuran, add 1 g of HOCH with stirring 2 CH 2 N(CH 3 ) 2 , The temperature is raised and refluxed for 1 hour. After the reaction was monitored by TLC, after the solvent was removed under reduced pressure, the reaction flask was poured into 50 ml of saturated brine, extracted with 60 ml of ethyl acetate three times, dried, and dissolved, and column chromatography yielded 0.31 g of the product, which is the compound 1-152, the yield is 51.8%. Melting point 80-82°C.

[0124] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0125] Compound 1-152: δ ppm 2.18 (3H, s), 2.41 (6H, s), 2.79 (2H, t), 4.45 (2H, t), 7.19 (1H, s), 7.39 (2H, m), 7.80- 7.88 (2H, m), 8.45 (1H, q), 10.14 (1H, s).

example 2

[0126] Example 2: Preparation of compound 2-2

[0127]

[0128] Take 1 g of IV-1 in a 100 ml reaction flask, add 50 ml of dioxane and intermediate H 2 NC(CH 3 ) 2 CN, reflux for 3 hours. After the reaction was monitored by TLC, after the solvent was removed under reduced pressure, 50 ml of saturated brine was poured into the reaction flask, and the mixture was extracted three times with 90 ml of ethyl acetate, dried, and dissolved. The column chromatographed to obtain the III-1 intermediate 0.63. Grams.

[0129] Dissolve the prepared intermediate III-1 in 60 ml of tetrahydrofuran, add 1 ml of triethylamine, add 1.02 g of acid chloride dropwise with stirring, and react at room temperature for 4 hours. After the reaction is monitored by TLC, process the product and obtain 0.45 g of product by column chromatography. , Namely compound 2-2, yield 31%. The melting point is 170-172°C.

[0130] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0131] Compound ...

example 3

[0132] Example 3: Preparation of Compound 2-6

[0133]

[0134] Take 0.5 g of II-2 in a 50 ml reaction flask, add 25 ml of acetonitrile, add 0.8 g of H under stirring 2 NC(CH 3 ) 2 CN, heated and refluxed for 3 hours. After the reaction was monitored by TLC, after the solvent was removed under reduced pressure, 50 ml of saturated brine was poured into the reaction flask, and the mixture was extracted three times with 90 ml of ethyl acetate, dried and dissolved, and column chromatography yielded 0.27 g of the product, which is the compound 2-6, the yield is 45.3%. The melting point is 140-142°C.

[0135] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0136] Compound 2-6: δppm 1.95 (6H, s), 2.65 (3H, s), 6.85 (1H, s), 7.28 (1H, q), 7.87 (1H, s), 7.92 (1H, d), 8.30 ( 1H, q), 8.48 (1H, s).

[0137] Other compounds of general formula I can be prepared by the preparation method provided by the present invention.

[0138] Melting point and nuclear magnetic ...

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Abstract

The invention discloses an anthranilic acid compound, of which the structure is shown in a general formula I, wherein the definitions of substitutional groups are shown in an instruction book. The anthranilic acid compound has broad-spectrum insecticidal activity, and in particular to spodoptera exigua hubner and diamond back moth, the compound has better activity, and can also achieve good control efficiency under the condition of low dose.

Description

Technical field [0001] The invention belongs to the field of pesticides, and specifically relates to an anthranilic acid compound, N-oxide, salt and composition, and their application as pesticides in agriculture or other fields. Background technique [0002] The control of invertebrate pests is extremely important in achieving high planting efficiency. Damage to growing and stored crops by invertebrate pests can cause a significant decrease in productivity, and therefore lead to increased costs for consumers. Many products for these purposes are available, but there is still a need for new compounds that are more effective, low-cost, low-toxic, environmentally safe, or have different modes of action. Anthranilic acid compounds (fish nitin receptors) are effective insecticides developed in recent years to control invertebrate pests. [0003] Patent WO03015519 discloses the following compounds with insecticidal activity: [0004] [0005] Patent WO2004033468 discloses the following...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D417/14C07D413/14C07D401/14A01N43/56A01P7/00A01P5/00
Inventor 刘长令柴宝山袁静彭永武张弘杨吉春李慧超
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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