Synthesis method for bifenazate

A technology of bifenazate and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of high cost and difficult industrial production, and achieve the effects of easy post-processing, increased yield, and shortened experimental steps

Inactive Publication Date: 2012-02-08
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As a known synthetic pesticide, bifenazate has many synthetic methods. It has been reported that 3-bromo-4-methoxy Biphenyl and 5-bromo-2-methoxyaniline were used as starting materials, and the target product [4-7] was obtained respectively through transition metal catalysis, and p-hydroxybiphenyl was used as raw material through the reaction with azo Amination reaction of diisopropyl dicarboxylate to obtain the product [8,9], but the cost is too high and it is difficult to carry out industrial production

Method used

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  • Synthesis method for bifenazate
  • Synthesis method for bifenazate
  • Synthesis method for bifenazate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of Compound Bifenazate (I)

[0032]

[0033] In a 250ml three-necked flask, 5g (29.4mmol) of p-hydroxybiphenyl was dissolved in 25ml of methyl tert-butyl ether (MTBE), mixed and stirred for 5min, and the temperature was controlled at 30°C. Take 4ml (58.8mmol, 2eq.) of nitric acid mixed with 10ml of MTBE and pour it into the dropping funnel, add dropwise within 1h, and continue to stir for 3h. TLC detects that the reaction ends. The system was poured into 300ml of ice water and stirred for 5 minutes. At this time, there was no dark orange liquid on the surface of the liquid surface, and a large amount of solids were precipitated. They were suction filtered and dried to obtain 5.9 g of yellow solid 3-nitro-4-hydroxybiphenyl (II). The rate is 93%.

[0034]

[0035]

[0036] 5 g (23.2 mmol) of the obtained 3-nitro-4-hydroxybiphenyl solid were mixed with 40 ml of dimethyl carbonate, 8.2 g (1.1 eq.) of tetrabutylammonium bromide (TBAB) and 3.2 ...

Embodiment 2

[0045] Embodiment 2: the preparation of compound bifenazate (I)

[0046]

[0047] In a 250ml three-necked flask, 5g (29.4mmol) of p-hydroxybiphenyl was dissolved in 25ml of methyl tert-butyl ether (MTBE), mixed and stirred for 5min, and the temperature was controlled at 20°C. Take 2ml (29.4mmol, 1eq.) of nitric acid mixed with 10ml of MTBE and pour it into the dropping funnel, add dropwise within 1h, and continue to stir for 3h. TLC detects that the reaction ends. The system was poured into 300ml of ice water and stirred for 5 minutes. At this time, there was no dark orange liquid on the surface of the liquid surface, and a large amount of solids were precipitated. They were suction filtered and dried to obtain 5.9 g of yellow solid 3-nitro-4-hydroxybiphenyl (II). The rate is 80%.

[0048]

[0049]

[0050] 5 g (23.2 mmol) of the obtained 3-nitro-4-hydroxybiphenyl solid were mixed with 30 ml of dimethyl carbonate, 8.2 g (1.1 eq.) of tetrabutylammonium bromide (TBAB) a...

Embodiment 3

[0057] Embodiment 3: the preparation of compound bifenazate (I)

[0058]

[0059] In a 250ml three-necked flask, 5g (29.4mmol) of p-hydroxybiphenyl was dissolved in 25ml of methyl tert-butyl ether (MTBE), mixed and stirred for 5min, and the temperature was controlled at 40°C. Take 2ml (58.8mmol, 2eq.) of nitric acid mixed with 10ml of MTBE and pour it into the dropping funnel. The dropwise addition is completed within 1h, and the stirring is continued for 3h. TLC detects that the reaction ends. The system was poured into 300ml of ice water and stirred for 5 minutes. At this time, there was no dark orange liquid on the surface of the liquid surface, and a large amount of solids were precipitated. They were suction filtered and dried to obtain 5.9 g of yellow solid 3-nitro-4-hydroxybiphenyl (II). The rate is 85%.

[0060]

[0061]

[0062] 5 g (23.2 mmol) of the obtained 3-nitro-4-hydroxybiphenyl solid were mixed with 30 ml of dimethyl carbonate, 8.2 g (1.1 eq.) of tetr...

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Abstract

The invention belongs to the technical field of pesticide and midbody synthesis, particularly relates to a synthesis method for bifenazate. In the synthesis method for the bifenazate, a target product is synthetized by taking para-hydroxydiphenyl as a raw material through nitration, methylation, hydrogenated reduction, diazotization, diazonium salt reduction and an acylation one-step method, wherein acylation reaction is directly performed on hydrazonium salt without treatment, thus, the experimental procedure is shortened, the yield is improved to above 65 percent from 50 percent, the conversion rate of a reaction product is high, and the purification treatment is easy to perform. The synthesis method for the bifenazate has the advantages that the operation is simple, the condition is mild, the yield is high, the cost is low, and the like, is easy to carry out industrial production and has a wide application prospect. The bifenazate synthetized by the invention can be used as a specific acaricide, is active in active stage of tetranychid, can also control pests, such as Tetranychus urticae, in the egg stage, and is used for cotton, hop and certain fruiter crops to effectively prevent all mites in the growth stage.

Description

technical field [0001] The invention belongs to the technical field of pesticide and intermediate synthesis, in particular to a method for synthesizing bifenazate. Background technique [0002] The chemical name of bifenazate is N'-(4-methoxybiphenyl-3-)hydrazine carboxylic acid isopropyl ester, which is a new type of hydrazine ester compound. It is a specific acaricide, which is active in the active stage of spider mites, and can also control the egg stage of pests such as spider mites. Effective against mites in all growth stages for cotton, hops and certain fruit crops [1] . The drug can provide rapid killing and long-residue selective control effect (no harm to beneficial mites and beneficial insects). It has been registered and applied in various states in the United States, but it has not been produced in China at present. [0003] Looking at the development history of the pesticide industry, the number of original pesticide varieties has increased from dozens in t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C281/02
Inventor 匡春香魏健黄振东
Owner TONGJI UNIV
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