Anthranilic acid compound and use thereof

A technology of anthranilic acid and compounds, applied in the field of anthranilic acid compounds, as pesticides, salts and compositions, and N-oxides, can solve the problems of reduced productivity and increased consumer costs

Active Publication Date: 2009-08-05
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

[0122] Example 1: Preparation of Compound 1-152

[0123]

[0124] Take 0.5 g of II-I in a 50 ml reaction flask, add 25 ml of tetrahydrofuran, and add 1 g of HOCH under stirring 2 CH 2 N(CH 3 ) 2 , heated to reflux for 1 hour. 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 0.31 grams of the product, namely the compound 1-152, yield 51.8%. The melting point is 80-82°C.

[0125] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0126] Compound 1-152: δppm 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

[0127] Example 2: Preparation of compound 2-2

[0128]

[0129] Take 1 g of IV-1 in a 100 ml reaction bottle, add 50 ml of dioxane and intermediate H 2 NC(CH 3 ) 2 CN, reflux reaction for 3 hours. After the completion of the reaction as monitored by TLC, after desolvation under reduced pressure, 50 ml of saturated saline was poured into the reaction flask, extracted three times with 90 ml of ethyl acetate, dried, and desolvated, and column chromatography gave III-1 intermediate 0.63 gram.

[0130] The prepared intermediate III-1 was dissolved in 60 ml of tetrahydrofuran, 1 ml of triethylamine was added, 1.02 g of acid chloride was added dropwise under stirring, and the reaction was carried out at room temperature for 4 hours. After the reaction was monitored by TLC, 0.45 g of the product was obtained by column chromatography , namely compound 2-2, the yield is 31%. The melting point is 170-172°C.

[0131] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl...

example 3

[0133] Example 3: Preparation of Compound 2-6

[0134]

[0135] Take 0.5 g of II-2 in a 50 ml reaction flask, add 25 ml of acetonitrile, and add 0.8 g of H 2 NC(CH 3 ) 2 CN, heated up and refluxed for 3 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 90 milliliters of ethyl acetate, dry, and desolventize, and obtain 0.27 grams of product by column chromatography, namely compound 2-6, yield 45.3%. The melting point is 140-142°C.

[0136] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0137] 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).

[0138] Other compounds of general formula I can be prepared by the preparation methods provided by the present invention.

[0139] Melting point and nuclear magnetic data ( 1 H...

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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 insecticides, and in particular relates to an anthranilic acid compound, N-oxide, salt and composition, and their application as insecticides in agriculture or other fields. Background technique [0002] Control of invertebrate pests is extremely important in achieving high planting efficiency. Damage to growing and stored crops by invertebrate pests 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. Anthranilic acid compounds (ryanodine 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 di...

Claims

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Application Information

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Patent Type & Authority Applications(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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