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Best Manufacturing Methods for Pest Control Agents

一种制造方法、化合物的技术,应用在植物学设备和方法、杀生剂、动物驱避剂等方向,能够解决不适合工业制造等问题,达到高收率的效果

Active Publication Date: 2022-05-10
MITSUI CHEM AGRO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the manufacturing method described in these documents is not suitable for industrial manufacturing

Method used

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  • Best Manufacturing Methods for Pest Control Agents
  • Best Manufacturing Methods for Pest Control Agents
  • Best Manufacturing Methods for Pest Control Agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Add 31.24g (0.22mol) of ethyl trifluoroacetate, 18.82g (0.20mol) of 2-aminopyridine, and 16g of N,N-dimethylformamide (DMF) in sequence, and add sodium methoxide (28.0% methanol solution) 38.57g (0.20mol). After stirring at 25° C. for 1 hour, methanol and ethanol were distilled off under reduced pressure. What dissolved 32.70 g (0.20 mol) of 2-chloro-5-chloromethylpyridine in 18.8 g of DMF was added there, and it stirred at 60 degreeC for 3 hours and 15 minutes. Then, 110 ml of water was added, and after stirring at room temperature for 3 hours, the precipitate was collected by filtration, pressure-washed twice with 40 ml of water, and 59.81 g of the target object (94.7% yield, purity 98.6%).

Embodiment 2~4 and comparative example 1

[0072] In Examples 2-4, as shown in Table 1, change the ethyl trifluoroacetate of step 1 in Example 1 relative to the equivalent of 2-aminopyridine to carry out the reaction, and obtain the yield and purity shown in Table 1. Target. In Comparative Example 1, the reaction was carried out by changing the equivalent of ethyl trifluoroacetate to 1 equivalent of 2-aminopyridine in Step 1 in Example 1 as shown in Table 1. As a result, although the target object was obtained, as shown in Table 1, it was an inferior result compared with the yield of Examples 1-4.

[0073]

Embodiment 5~7 and comparative example 2 and 3

[0075] In Examples 5 to 7, as shown in Table 2, change the sodium methylate of Step 1 in Example 1 relative to 1 equivalent of 2-aminopyridine to carry out the reaction, and obtain the yield and purity targets shown in Table 2. thing. In Comparative Examples 2 and 3, the reaction was carried out by changing the equivalent of sodium methoxide to 1 equivalent of 2-aminopyridine in Step 1 in Example 1 as shown in Table 2. As a result, although the target object was obtained, as shown in Table 2, it was an inferior result compared with the yield of Example 1, 5-7.

[0076]

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Abstract

Using the compound represented by the following formula (A) as a starting material, the compound represented by the following formula (I) is produced through the intermediate represented by the following formula (B) produced using trifluoroacetate and metal alkali compound method.

Description

technical field [0001] The present invention relates to an optimal production method of pest control agents having a 2-acyliminopyridine structure. Background technique [0002] N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide represented by the following formula (I) etc. 2 -Acyliminopyridine derivatives are useful compounds as pest control agents (Patent Document 1). [0003] As a method for producing a pest control agent having a 2-acyliminopyridine structure, prior art documents (Patent Documents 1 to 4) are known. [0004] Patent Documents 1 and 2 describe a method for producing a compound represented by formula (I) by an acylation reaction using trifluoroacetate. However, the amount of trifluoroacetate reagent used is large and the yield is low. Patent Document 4 also describes a method for producing the aforementioned compound using trifluoroacetate, but the yield is low and a long time is required for the reaction. Therefore, the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/75
CPCC07D213/75A01N43/40A01N47/40
Inventor 橘田繁辉中西希鹫见信二郎
Owner MITSUI CHEM AGRO INC