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New method for synthetizing tolfenpyrad

A technology of pyrenpyrad and a new method, which is applied in the field of synthesis of insecticide and acaricide-fenpyran, can solve the problems of three wastes, many reaction steps, and high cost

Inactive Publication Date: 2013-07-10
YANCHENG TEACHERS UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the deficiencies of many reaction steps, high cost and many wastes in the prior art, the main purpose of the present invention is to provide a new method for synthesizing tofenpyrad, which is characterized in that 4-chloro-5-ethylpyridine is made Azole-2-carboxylate and 4-(4-methylphenoxy)benzylamine are directly subjected to aminolysis reaction to obtain pyrenpyrad

Method used

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  • New method for synthetizing tolfenpyrad

Examples

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Comparison scheme
Effect test

Embodiment 1

[0013] Embodiment 1: the aminolysis of Ia-make catalyst with titanium tetrachloride

[0014] 101.3g Ia and 106.6g II, 9.38g titanium tetrachloride, and 300ml toluene are placed in a four-necked flask, heated up to 80°C, kept for 8h, and the conversion rate of Ia detected by gas chromatography reaches 87.2%, and the conversion rate of Ia after 12h Reached 93.3%. After cooling, add 300 mL of water and stir for 30 min, separate the organic layer, wash with water, and remove the solvent to obtain a brownish-red solid, which is recrystallized from a mixed solution of ethyl acetate-petroleum ether (1:1) to obtain pyrenpyrrole, an off-white solid 125 g , Yield: 65.0%.

Embodiment 2

[0015] Embodiment 2: the aminolysis of Ia-use titanium tetrachloride to make the solvent-free reaction of catalyst

[0016] 101.3g Ia, 106.6g II, 9.38g titanium tetrachloride were placed in a four-necked flask, and the temperature was raised to 130-140°C. After 6 hours, the conversion rate of Ia was detected by gas chromatography to reach 85.7%, and after 7 hours, the conversion rate of Ia reached 93.5%. %. After cooling, add 300mL of water and 500mL of dichloroethane and stir for 30min, separate the organic layer, wash with water, and remove the solvent to obtain a brownish red solid, which is recrystallized from a mixed solution of ethyl acetate-petroleum ether (1:1) to obtain azoles Amide, off-white solid 134.4g, yield: 70%.

Embodiment 3

[0017] Embodiment 3: the aminolysis of Ib-make catalyst with tetraisopropyl titanate

[0018] 108g Ib, 106.6g II, 9.35g tetraisopropyl titanate, and 600mL chlorobenzene were placed in a four-necked flask, and the temperature was raised to 130°C. After 6 hours, the conversion rate of Ib was detected by gas chromatography to reach 81.5%. After 10 hours, the conversion rate of Ib was The rate reached 94.6%. After cooling, add 600mL of water and stir for 30min, separate the organic layer, wash with water, and remove the solvent to obtain a brown-red solid, which is recrystallized from a mixed solution of ethyl acetate-petroleum ether (1:1) to obtain pyrenpyrrole, an off-white solid 130g , Yield: 68%.

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Abstract

The invention relates to a new method for synthetizing tolfenpyrad. The key of the new method is that ethyl 1-methyl-3-ethyl-4-chloro-5-pyrazolecarboxylate and 4-(4-methyl phenoxyl)benzylamine are directly subjected to an aminolysis reaction by using an acid catalyst to synthesize tolfenpyrad; and compared with the steps in the prior art, the reaction steps are shortened by two steps.

Description

technical field [0001] The present invention relates to a new method for the synthesis of insecticide and acaricide-fenpyran, the key of the present invention is to change the synthetic route of tofenpyrad reported in the literature, and use 4-chloro-5-ethylpyrazole under the catalysis of acidic catalyst -2-Formic acid ester and 4-(4-methylphenoxy)benzylamine were directly subjected to aminolysis reaction to synthesize tofenpyrad. Compared with the literature, its reaction steps are shortened by two steps. Background of the invention [0002] Fenpyramid was discovered by Mitsubishi Chemical Co., and its activity was reported by T. Kukuchi et al. It was tested in Japan in 1996 and registered in 2002. It is a new type of pyrazole insecticide and acaricide jointly developed by Mitsubishi and Otsuka Chemical Co. , and listed under the trade name Hachi-hachi, and sold in many countries; in 2009, Nippon Nosho Chemical Co., Ltd. obtained provisional registration of 98% technical a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/16
Inventor 杨锦明李玉峰沈小娟马鸿飞左杭冬
Owner YANCHENG TEACHERS UNIV
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