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Preparation method of fipronil derivatives

A technology of fipronil and derivatives, which is applied in the field of preparation of fipronil derivative HNPC-A8008, which can solve the problems of raw material consumption and synthesis cost, difficulty in industrialization, complicated operation, etc., and achieve less three wastes and lower precipitation temperature , The effect of simple process

Active Publication Date: 2018-10-23
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In the above method, there are disadvantages such as low yield, high raw material consumption and synthesis cost, complicated operation, etc., and it is difficult to realize industrialization

Method used

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  • Preparation method of fipronil derivatives
  • Preparation method of fipronil derivatives
  • Preparation method of fipronil derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 437.2g (1.0mol) of fipronil, 58.8g (1.05mol) KOH and 1000mL of methanol to a 3000mL three-necked flask equipped with a thermometer, condenser, constant pressure dropping funnel, and stirrer, and start stirring. 111.0 g (1.0 mol) of 1,3-transdichloropropene was added dropwise at -10°C. After the drop was complete, the temperature was controlled at -10°C for 24 hours. After the reaction is completed, filter the filtrate to adjust the pH value of the system to neutral with concentrated hydrochloric acid, recover the solvent under negative pressure below 40 ° C, slowly add the residue to ice water, control the temperature at 0 ° C ~ 5 ° C, stir and crystallize, filter, and the filter residue is reconstituted with methanol. Crystallization, filtration, and drying gave 380.6 g of white crystalline solid. The yield was 71.7%, and the quantitative analysis content by liquid chromatography was 96.4%. 1 HNMR (CDCl 3 / TMS): δ (ppm): 3.730 (d, 2H, CH 2 ), 5.681 (m, 1H, CH=),...

Embodiment 2

[0016] Add 437.2g (1.0mol) of fipronil, 159g (1.5mol) of Na 2 CO 3 and 1500mL of ethanol, start stirring, dropwise add 149.9g (1.35mol) 1,3-transdichloropropene at 10°C, after dropping, control the temperature at 20°C for 15 hours. After the reaction is completed, filter the filtrate to adjust the pH value of the system to neutral with concentrated hydrochloric acid, recover the solvent under negative pressure below 40 ° C, slowly add the residue to ice water, control the temperature at 0 ° C ~ 5 ° C, stir and crystallize, filter, and the filter residue is reconstituted with methanol. Crystallization, filtration, and drying gave 375.8 g of white crystalline solid. The yield was 70.5%, and the quantitative analysis content by liquid chromatography was 96.0%.

Embodiment 3

[0018] Add 437.2g (1.0mol) of fipronil, 179.4g (1.3mol) of K 2 CO 3 And 1300mL of n-propanol, start stirring, add 127.7g (1.15mol) of 1,3-transdichloropropene dropwise at 0°C, after dropping, control the temperature at 0°C for 22 hours. After the reaction is completed, filter the filtrate to adjust the pH value of the system to neutral with concentrated hydrochloric acid, recover the solvent under negative pressure below 40 ° C, slowly add the residue to ice water, control the temperature at 0 ° C ~ 5 ° C, stir and crystallize, filter, and the filter residue is reconstituted with methanol. Crystallization, filtration, and drying gave 386.0 g of white crystalline solid. The yield was 72.5%, and the quantitative analysis content by liquid chromatography was 96.1%.

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Abstract

The invention discloses a preparation method of fipronil derivative HNPC-A 8088, comprising: under the action of an organic solvent methanol, ethanol, n-propanol or butanone, and an inorganic alkali KOH, NaOH, Na2CO3 or K2CO3, reacting fipronil with trans-1,3-dichlorpropylene, and after reacting, performing filtering, desolventizing, filtering and recrystallizing to obtain the finished fipronil derivative HNPC-A 8088 >95% in mass content, having a following chemical reaction formula. A low-boiling-point organic matter is used as a reaction solvent so that product desolventizing temperature is reduced, the solvent is easy to recycle, reaction conditions are mild, operation is safe, product yield is greatly increased, a post-treatment method has simple process and low three wastes, saves energy and reduces consumption, and solved are the problems: the prior art is low in yield and high in cost, the organic solvent for use has a high boiling point, the product HNPC-A 8008 thermally decomposes easily if rectification desolventizing temperature is high, and there is a need for column chromatography to obtain a product while column chromatography is high in cost, low in capacity and difficult to industrialize.

Description

technical field [0001] The invention relates to a preparation method of fipronil derivatives, especially a preparation method of fipronil derivative HNPC-A8008. Background technique [0002] Fipronil derivative HNPC-A8008 is a new broad-spectrum insecticide independently designed and synthesized by Hunan Research Institute of Chemical Industry. It not only has excellent biological activity against Lepidoptera pests, but also exhibits high killing activity against Coleoptera and Homoptera insects. It has low toxicity to humans and animals and is safe to crops. The toxicity to zebrafish is low toxicity, which solves the toxicity problem of pyrazole compounds to aquatic organisms. The chemical structural formula of HNPC-A8008 is: [0003] [0004] The preparation method of HNPC-A8008 disclosed in the literature is: in the presence of potassium hydroxide, using N,N-dimethylformamide (DMF) or tetrahydrofuran (THF) as solvent, from fipronil 1,3-trans dichloropropene Reactio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/44
CPCC07D231/44
Inventor 杜升华兰世林刘卫东刘源黄超群王艳丽罗亮明
Owner HUNAN CHEM RES INST
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