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Acetylamine derivative containing thienyl pyridine and sulfur group and preparation method and application thereof

A technology of thienylpyridine and acetoarylamide is applied in the field of acetoarylamide derivatives and their preparation, which can solve the problems of the preparation of pyrazolecarboxamide derivatives and the undisclosed insecticidal activity, and achieves high insecticidal activity, good insecticidal activity, and the like. Control the effect of the effect

Active Publication Date: 2021-08-06
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, a sulfur-containing aryl-substituted pyrazole carboxamide derivative as shown in the present invention and its preparation and insecticidal activity have not been disclosed

Method used

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  • Acetylamine derivative containing thienyl pyridine and sulfur group and preparation method and application thereof
  • Acetylamine derivative containing thienyl pyridine and sulfur group and preparation method and application thereof
  • Acetylamine derivative containing thienyl pyridine and sulfur group and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Compound I-3 (2-((3-cyano-6-methyl-4-(thiophen-2-yl)pyridin-2-yl)thio)-N-(4-fluorophenyl)acetamide) method of preparation.

[0038] The reaction scheme is shown in the following formula:

[0039]

[0040] The preparation method is as follows:

[0041] Step 1: Preparation of 2-chloro-6-methyl-4-(thiophen-2-yl)nicotinonitrile (compound of formula A1)

[0042]

[0043] Prepared by referring to the method in the literature (J.Chem., 2013, 2013: 1-7; ACS Omega, 2019, 4: 8406-8412).

[0044] Add ethanol (250mL), 2-thiophenecarbaldehyde (11.22g), ethyl cyanoacetate (11.31g) and acetone (5.81g) into a 500mL two-necked flask in turn, and add ammonium acetate (23.12g) while stirring at room temperature. The mixture was heated to reflux for 12 hours, then cooled to room temperature, a solid precipitated, filtered, washed with ethanol, and dried to give a yellow solid 6-methyl-2-oxo-4-(thiophen-2-yl)-1,2- Dihydropyridine-3-carbonitrile was directly put into the next react...

Embodiment 2

[0054] Compound I-11 (2-((3-cyano-6-methyl-4-(thiophen-2-yl)pyridin-2-yl)thio)-N-(2,4,6-trichlorobenzene base) the preparation method of acetamide).

[0055] The reaction scheme is shown in the following formula:

[0056]

[0057] The preparation method is as follows:

[0058] Step 1: Preparation of 2-mercapto-6-methyl-4-(thiophen-2-yl)nicotinonitrile (compound of formula B1)

[0059]

[0060] Prepared according to the method in the literature (J.Chem., 2013, 2013: 1-7).

[0061] The compound of formula A1 (2-chloro-6-methyl-4-(thiophen-2-yl)nicotinonitrile) (7.04g), ethanol (100mL), and thiourea (4.57g) were sequentially added into a 250mL two-necked bottle, Heated to reflux and reacted for 8 hours. The system was cooled to room temperature, a solid was precipitated, filtered, washed with ethanol, and dried to obtain 2-mercapto-6-methyl-4-(thiophen-2-yl)nicotinonitrile (compound of formula B1) as a yellow solid.

[0062] Step 2: Preparation of 2-chloro-N-(2,4,6-tri...

Embodiment 3

[0070] Compound I-12 (2-((3-cyano-6-methyl-4-(5-methylthiophen-2-yl)pyridin-2-yl)thio)-N-(3-fluorophenyl ) the preparation method of acetamide).

[0071] The reaction scheme is shown in the following formula:

[0072]

[0073] The preparation method is as follows:

[0074] Step 1: Preparation of 2-chloro-6-methyl-4-(5-methylthiophen-2-yl)nicotinonitrile (compound of formula A2)

[0075]

[0076] Prepared by referring to the method in the literature (J.Chem., 2013, 2013: 1-7; ACS Omega, 2019, 4: 8406-8412).

[0077] Add ethanol (250mL), 5-methylthiophene-2-carbaldehyde (12.62g), ethyl cyanoacetate (11.31g) and acetone (5.81g) into a 500mL two-necked flask in sequence, and add ammonium acetate ( 23.12g). The mixture was heated to reflux for 12 hours, then cooled to room temperature, a solid was precipitated, filtered, washed with ethanol, and dried to obtain a yellow solid, which was directly put into the next reaction.

[0078] 6-methyl-4-(5-methylthiophen-2-yl)-2-ox...

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Abstract

The invention relates to an acetyl arylamine derivative containing thienyl pyridine and a sulfur group and a preparation method and application thereof. On the basis of intermediates such as sulfur-containing substituted pyridine, a compound obtained through a series of reactions is shown as a general formula I, the compound represented by the general formula I has good insecticidal activity, is especially effective for oriental armyworm and plutella xylostella, can be used as an active component of an insecticidal composition, and is used for preparing an agricultural insecticide and preventing and treating agricultural insect pests.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides, and in particular relates to an acetylarylamine derivative containing thienylpyridine and sulfur groups, a preparation method and application thereof. Background technique [0002] The continuous discovery and research of new insecticidal compounds is of great significance. With the long-term or excessive use of existing insecticide varieties, they may be gradually eliminated due to problems such as the emergence of pest resistance and ecological environment pollution, and the development of insecticides with novel structure types can continue to be used as substitutes. crop protection. [0003] Heterocyclic compounds widely exist in nature, and most of the important compounds related to biology are heterocyclic compounds. Compounds containing heterocyclic groups often have a variety of properties, some of which can be used as drugs, insecticides, herbicides, dyes, plastics, etc. For e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/04A01N43/40A01P7/00A01P7/04
CPCC07D409/04A01N43/40
Inventor 王宝雷李欢杨娜熊丽霞李正名
Owner NANKAI UNIV
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