Novel chlorine-containing bifenthrin and preparation method and application thereof

A new type of technology for bifenthrin, which is applied in the field of preparation of new bifenthrin-containing bifenthrin, can solve the problems of poor drug efficacy, achieve strong biological activity, simple preparation method, and good killing effect

Active Publication Date: 2019-06-18
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The invention provides a new type of bifenthrin, its preparation method and its application, and solves the technical problems that existing pyrethroids are prone to potential toxicity and have poor drug efficacy in the prior art

Method used

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  • Novel chlorine-containing bifenthrin and preparation method and application thereof
  • Novel chlorine-containing bifenthrin and preparation method and application thereof
  • Novel chlorine-containing bifenthrin and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of novel bifenthrin (SZ-B-02):

[0037]

[0038] First, obtain Intermediate A through continuous reaction, add 548.0mg (1.0mmol) Intermediate A in a 100ml round bottom flask, add 850.0mg (4.0mmol) of potassium phosphate simultaneously, add 36.6mg (0.05mmol) of [ 1,1-bis(diphenylphosphino)ferrocene]palladium dichloride, then add 236.1mg (1.5mmol) of 2-chloro-5-pyridineboronic acid, dissolve in 30ml of toluene solution, and place in an oil pan React at 100°C for 12 hours; secondly, determine the end point of the reaction by thin layer chromatography, filter the above reaction solution with suction to remove the solid in the reaction, and rotary evaporate the filtrate after suction filtration to obtain the crude product; finally, extract and wash , drying, filtration, rotary evaporation and column chromatography and other purification processes to obtain the target compound SZ-B-02 with a yield of 71%. 1 H NMR (400MHz, CDCl 3 )δ8.43(d,1H),7.75(dd,J=8.2,2.3...

Embodiment 2

[0040] Preparation of novel bifenthrin (SZ-B-04):

[0041]

[0042] First, obtain Intermediate A through continuous reaction, add 548.0mg (1.0mmol) Intermediate A in a 100ml round bottom flask, add 850.0mg (4.0mmol) of potassium phosphate simultaneously, add 36.6mg (0.05mmol) of [ 1,1-bis(diphenylphosphino)ferrocene]palladium dichloride, then add 263.8mg (1.5mmol) of 3,4,5-trifluorophenylboronic acid, dissolve in 30ml of toluene solution, in the oil domain React in the pot at 100°C for 12 hours; secondly, determine the end point of the reaction by thin layer chromatography, filter the above reaction solution with suction to remove the solid in the reaction, and rotary evaporate the filtrate after suction filtration to obtain the crude product; finally, extract , washing, drying, filtration, rotary evaporation and column chromatography to obtain the target compound SZ-B-04 with a yield of 65%. 1 H NMR (400MHz, CDCl 3 )δ7.46(dd, J=7.7,1.5Hz,1H),7.36(t,J=7.6Hz,1H),7.26(dd,1H...

Embodiment 3

[0044]Preparation of novel bifenthrin (SZ-B-05):

[0045]

[0046] First, obtain Intermediate A through continuous reaction, add 548.0mg (1.0mmol) Intermediate A in a 100ml round bottom flask, add 850.0mg (4.0mmol) of potassium phosphate simultaneously, add 36.6mg (0.05mmol) of [ 1,1-bis(diphenylphosphino)ferrocene]palladium dichloride, then add 284.8mg (1.5mmol) of 4-trifluoromethylbenzeneboronic acid, dissolve in 30ml of toluene solution, and place in an oil pan React at 100°C for 12 hours; secondly, determine the end point of the reaction by thin layer chromatography, filter the above reaction solution with suction to remove the solid in the reaction, and rotary evaporate the filtrate after suction filtration to obtain the crude product; finally, extract and wash , drying, filtration, rotary evaporation and column chromatography and other purification processes to obtain the target compound SZ-B-05 with a yield of 39%.

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Abstract

The invention relates to the technical field of pesticides, in particular to novel chlorine-containing bifenthrin, a preparation method thereof and application of the novel chlorine-containing bifenthrin in anti-mosquito drugs. The novel chlorine-containing bifenthrin is as shown in structural formula I. The preparation method includes: adding an intermediate A as shown in structural formula II and a compound B as shown in structural formula III into solvent toluene, adding potassium phosphate, and adding a catalyst to perform reaction to obtain the novel chlorine-containing bifenthrin. By thenovel chlorine-containing bifenthrin and the preparation method and application thereof, the technical problems that existing pyrethroid in the prior art easily generates potential toxicity and is poor in pesticide effect are solved.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a novel bifenthrin, a preparation method and an application thereof. Background technique [0002] Aedes albopictus, also known as the Asian tiger mosquito, belongs to the mosquito family Diptera, which originated in Southeast Asia and is a common mosquito species in Southeast Asia and China. Aedes albopictus is both a very aggressive mosquito and an important viral vector that transmits many pathogens, including dengue fever, Ross River virus and West Nile virus. The eggs of Aedes albopictus have strong cold resistance and vitality, and are easy to be carried and spread, so that Aedes albopictus can invade new territories and develop into a dominant mosquito species, becoming the fastest-spreading 100 species in the world in the past 20 years. one of the species. It has spread from its origin in Asia to more than 70 countries around the world. [0003] Pesticides currently...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61C07C67/293C07C69/747C07C253/30C07C255/55A01P7/04
Inventor 张焜杨洋赵肃清朱秋燕林锦斌
Owner GUANGDONG UNIV OF TECH
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