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Quaternary ammonium salt compound and application thereof

A technology of quaternary ammonium salts and compounds, applied in the field of agricultural herbicides, can solve problems such as herbicide resistance

Active Publication Date: 2016-05-11
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In order to develop novel herbicides to solve the increasingly serious problem of herbicide resistance, the invention provides a quaternary ammonium salt compound and its application

Method used

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  • Quaternary ammonium salt compound and application thereof
  • Quaternary ammonium salt compound and application thereof
  • Quaternary ammonium salt compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0191] Example 1 Preparation of Compound (63)

[0192]

[0193] 1) Preparation of intermediate (VII-1)

[0194] Dissolve 10g sodium carbonate (0.1mol) in water, add 200ml toluene after dissolution, add 10g 2,6-diethylaniline (0.068mol), add 7.7g chloroacetyl chloride (0.068mol) dropwise under ice bath, stir at room temperature 2 After hours, TLC monitored the completion of the reaction, the reaction mixture was filtered off with suction, washed with water, and washed with petroleum ether to obtain a pink solid (VII-1). Melting point 122-124℃

[0195] 2) Preparation of intermediate (IV-1)

[0196] Add 13g of (VII-1) (0.058mol) into a 500ml three-necked flask, add 200ml of acetonitrile, add 12g of potassium carbonate (0.087mol), add 4.2g of diethylamine (0.058mol) dropwise, heat and reflux for 3 hours, the solution becomes light yellow turbid. After the completion of the reaction, the reaction mixture was suction filtered, and the filtrate was desolvated to obtain a yellow solid (IV-...

Embodiment 2

[0201] Example 2 Preparation of Compound (15)

[0202]

[0203] The preparation method refers to step 4) of Example 1. White solid, melting point 230.5°C. 1H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δppm 1.07 (6H, t), 1.42 (6H, t), 2.43 (4H, m), 3.46 (4H, m), 4.46 (6H, s), 6.77 (3H, d), 7.19 (2H, d) ), 7.42 (6H, m), 8.86 (1H, s).

Embodiment 3

[0204] Example 3 Preparation of Compound (31)

[0205]

[0206] The preparation method refers to step 4) of Example 1. White solid, melting point 165°C. 1H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δppm 1.12 (6H, t), 1.47 (6H, t), 2.53 (4H, d), 3.56 (4H, m), 3.85 (6H, s), 4.14 (2H, s), 4.81 (2H, d) ), 7.16 (2H, d), 7.19 (2H, d), 7.33 (2H, d), 7.54 (4H, s).

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Abstract

Belonging to the field of agricultural herbicides, the invention in particular relates to a quaternary ammonium salt compound and application thereof. The quaternary ammonium salt compound is shown as general formula (I). The general formula (I) compound has very good herbicidal activity, can effectively control barnyard grass, Abutilon theophrasti, Green Bristlegrass Herb, Zinnia elegans and other weeds, can achieve a good weeding effect under a low dosage, and is safe to corn and cotton before emergence and safe to wheat and corn after emergence. (general formula (I)).

Description

Technical field [0001] The invention belongs to the field of agricultural herbicides, and specifically relates to a quaternary ammonium salt compound and its application. Background technique [0002] Patent EP0638843A2 and US3080327A disclose compounds of the following general formula as developer and denatured ethanol additives. [0003] [0004] X is halogen, hydroxy, substituted benzoic acid, etc. [0005] Among them, the patent EP0638843A2 specification page 5 discloses compound A (the patent is numbered I-4). [0006] [0007] In the prior art, there is no report on the herbicidal activity of the compound represented by the general formula (I) of the present invention. Summary of the invention [0008] In order to develop new herbicides to solve the increasingly serious problem of herbicide resistance, the present invention provides a quaternary ammonium compound and its application. [0009] In order to achieve the above objectives, the technical solutions adopted by the present...

Claims

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Application Information

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IPC IPC(8): C07C237/04C07D401/04C07D241/44C07K5/062A01P13/00
Inventor 杨吉春吴峤崔东亮关爱莹马宏娟刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD