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N-substituted alkyl arylxoy phenoxyl propanamide compound with herbicidal activity and preparation and application thereof

An alkylphenoxypropionamide and compound technology, which is applied in the field of weed compounds, can solve the problems of insufficient safety, no description of rice safety, inability to meet agricultural production requirements, etc., and achieves broad herbicidal spectrum and excellent activity. Effect

Inactive Publication Date: 2016-03-23
周银平
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Chinese patent CN201310273568.6 reports that the compound (P-3) has good biological activity, and has good safety to rice at low doses (active ingredient 8 g/mu), but the patent does not indicate that it is effective on rice at high doses. safety, the active in

Method used

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  • N-substituted alkyl arylxoy phenoxyl propanamide compound with herbicidal activity and preparation and application thereof
  • N-substituted alkyl arylxoy phenoxyl propanamide compound with herbicidal activity and preparation and application thereof
  • N-substituted alkyl arylxoy phenoxyl propanamide compound with herbicidal activity and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The preparation of embodiment 1 compound 2

[0049]

[0050] (1) Preparation of Intermediate IV

[0051] Add 33.3 grams of intermediate III (prepared according to the method described in patent CN201310606528.9) into a 250 ml four-neck flask, add 150 ml of dichloroethane and 11.8 grams of thionyl chloride. Heated and refluxed for 10 hours. After the reaction is complete, remove the solvent to obtain Intermediate IV, add 150ml of dichloroethane, and cool down to 30°C for use.

[0052] (2) Preparation of Compound 2

[0053] 14 g of ethyl aminoacetate hydrochloride was added to the above-prepared solution, stirred and reacted for 1 hour, 12 g of triethylamine was added dropwise, and a large amount of white solid was precipitated. React for 2 hours. After the reaction was completed, 100 ml of water was added and stirred for 1 hour, then suction filtered and dried to obtain 38 g of the product. Content 96%. Yield 91%.

Embodiment 2

[0054] The preparation of embodiment 2 compound 3

[0055]

[0056] (1) Preparation of N-methylglycyl amino acid methyl ester

[0057] 12.6 grams of glycine methyl ester hydrochloride was added to a 250ml four-necked flask, and 150ml of ethanol and 11 grams of sodium carbonate were added. The temperature was raised to reflux, and 9.5 g of methyl bromide was added dropwise under the reflux state. After the dropwise addition was completed, the reaction was carried out under reflux for 4 hours. After the reaction is complete, cool down to room temperature, filter out the solid with suction, and remove ethanol to obtain N-methylglycinate methyl ester.

[0058] (2) Preparation of compound 3

[0059] The obtained N-methylglycyl amino acid methyl ester was added to the acid chloride solution (prepared by the above method), stirred and reacted at room temperature for 1 hour, 12 g of triethylamine was added dropwise, and a large amount of white solid was precipitated. React for 2...

Embodiment 3

[0060] The preparation of embodiment 3 compound 5

[0061]

[0062] (1) Preparation of Intermediate A

[0063] 11.6 grams of propionaldehyde and 14 grams of hydroxylamine hydrochloride were added to a 250 ml four-necked reaction flask, 100 ml of ethanol and 8 grams of sodium hydroxide were added, and the temperature was raised to reflux for 4 hours to complete the reaction. Ethanol was removed to obtain 13 grams of propionaldehyde oxime.

[0064] Add 11 grams of propionaldoxime into a 250 ml four-neck flask, add 100 ml of dichloroethane, and dropwise add 30 grams of 2-bromoacetyl bromide. After the dropwise addition, continue to add 15 grams of triethylamine dropwise. After the dropwise addition, the stirring reaction was continued for 4 hours. After the reaction was completed, 25.6 g of Intermediate A-1 was obtained, with a content of 97%.

[0065] Add 14.7 grams of phthalimide, 4 grams of sodium hydroxide, and 100 ml of N,N-dimethylformamide into a 250 ml four-neck rea...

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Abstract

The invention discloses an N-substituted alkyl arylxoy phenoxyl propanamide compound shown in the formula (I), a preparation method, a weeding composition and application of the composition for controlling malignant grassy weed in a rice field.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a compound that can be used in paddy fields to control weeds such as barnyardgrass and its preparation and application. Background technique [0002] Aryloxyphenoxy compounds have high activity in controlling grass weeds, and have been commercially developed in many varieties, such as fenoxaprop-ethyl, clodinafop-propargyl, etc. Because these compounds have high biological activity on gramineous plants, only a few can be used in rice, wheat and other gramineous crop fields. So far, there are only two aryloxyphenoxypropionate compounds that have been successfully used for post-emergence weeding in rice fields: 1. Cyhalofop-methyl (P-1) was developed and produced by Dow AgroSciences in 1987. The aryloxyphenoxypropionate herbicide used for weeding in paddy fields has good control effect on Paddy chinensis. The disadvantage is that it has very poor control effect on vicious gr...

Claims

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Application Information

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IPC IPC(8): C07D263/58A01N43/76A01P13/02
CPCA01N43/76C07D263/58
Inventor 周银平
Owner 周银平
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