Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Novel bifenthrin derivatives, and preparation method and application thereof

A technology for bifenthrin and derivatives, applied in the field of novel bifenthrin derivatives and their preparation, can solve problems such as interference with organism functions, threats to human and animal health, adverse effects on children's health, etc., and achieve excellent insecticide Mosquito-killing effect, effect of improving insecticidal and mosquito-killing effect and metabolic stability, excellent insecticidal effect

Inactive Publication Date: 2019-08-20
GUANGDONG UNIV OF TECH
View PDF11 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] More and more studies have found that pyrethroids can interfere with the normal function of organisms and pose a considerable threat to human and animal health
Studies have shown that long-term exposure to pyrethroid-containing environments will have adverse effects on the health of humans, especially children

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Novel bifenthrin derivatives, and preparation method and application thereof
  • Novel bifenthrin derivatives, and preparation method and application thereof
  • Novel bifenthrin derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1 compound intermediate B (B 1 ,B 2 ,B 3 )Synthesis

[0068] 1. Synthetic route

[0069]

[0070] Among them, the condition (a) is LiTMP, THF, -78~-60℃, 2~3h / CO 2 ,-60~-50℃, 2~3h.

[0071] 2. Synthesis steps

[0072] (1) After cleaning and drying the reaction vessel, use high-purity ultra-dry nitrogen as the reaction protection gas, pay attention to removing all the air in the reaction vessel, and do a good job of nitrogen balloon protection;

[0073] (2) Add 60mL ultra-dry tetrahydrofuran (THF) containing molecular sieves under nitrogen protection, then take anhydrous diisopropylamine (30mmol, 8.41mL) under nitrogen protection, carry out magnetic stirring, and put it in a Dewar flask, Add 300±5mL of ethyl acetate into the Dewar flask, slowly add crushed dry ice, so that the reaction temperature drops below -20°C, and stir at low temperature for 10 minutes;

[0074] (3) Under nitrogen protection, add n-butyllithium (2.5M, 30mmol, 12mL) into the reac...

Embodiment 2

[0077] Embodiment 2 compound intermediate C (C 1 ,C 2 ,C 3 )Synthesis

[0078] 1. Synthetic route

[0079]

[0080] Wherein, condition (b) is (COCl) 2 ,CH 2 Cl 2 ,DMF / Pyr,CH 3 OH, 2~3h, r.t.

[0081] 2. Synthesis steps

[0082] (1) Take by weighing the compound intermediate B (B) of Example 1 after purification 1 ,B 2 ,B 3 ) (1g, 3.16mmol, 3.16mmol, 3.54mmol), under the protection of nitrogen, add 20mL of ultra-dry anhydrous dichloromethane (DCM) and stir to dissolve it completely, then add three times the amount of oxalyl chloride (9.48mmol , 9.48mmol, 10.62 mmol), stirred for 20-30min;

[0083] (2) Under the protection of nitrogen, add 0.1mL of anhydrous grade N,N-dimethylformamide (DMF), react at room temperature for 1h, dry the activated product in vacuum, and keep as much as possible during the operation. It is possible to reduce the entry of external air into the reaction device; use nitrogen as a protective gas, add ultra-dry dichloromethane solvent, sti...

Embodiment 3

[0085] Embodiment 3 compound intermediate D (D 1 ,D 2 ,D 3 )Synthesis

[0086] 1. Synthetic route

[0087]

[0088] Among them, condition (c) is LiBH 4 , toluene, 100~105℃, 30~35min.

[0089] 2. Synthesis steps

[0090] (1) Take by weighing the purified intermediate compound C of Example 2 (C 1 ,C 2 ,C 3 ) (0.5g, 1.51mmol, 1.51mmol, 1.69mmol), use nitrogen as protective gas, add 20mL of toluene solvent, add lithium borohydride (1.81mmol, 1.81mmol, 2.03mmol), and React in an oil bath for 30-35 minutes, and detect the end point of the reaction by TLC [developing solvent: V (petroleum ether) / V (ethyl acetate) = 6 / 1];

[0091] (2) After the reaction is completed, under magnetic stirring, slowly add HCl solution with a concentration of 4M to adjust the pH value of the system to 3-4, add 50mL of deionized water, extract directly with ethyl acetate three times, and use anhydrous MgSO 4 Dry, then filter, concentrate, obtain compound intermediate D (D 1 ,D 2 ,D 3 ) crud...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses novel bifenthrin derivatives, and a preparation method and application thereof. The novel bifenthrin derivatives have a structural formula as shown in a formula (I) which is described in the specification. In the formula (I), when R1 is H, R2 is a Cl or CF3 substituent group, and R3 is H or a substituted or unsubstituted non-heterocyclic or heterocyclic aryl group; when R1is a Cl substituted group, R 2 is H or a Cl or CF3 substituent group, and R3 is H or a substituted or unsubstituted non-heterocyclic or heterocyclic aryl group; the non-heterocyclic aryl group is a phenyl, naphthyl, anthryl, phenanthryl or pyrenyl group; and the heterocyclic aryl group is a five-to-nine-membered monocyclic or polycyclic heterocyclic aryl group with one or more O or S heteroatoms.According to the invention, a series of the novel bifenthrin derivatives are synthesized mainly by modifying and transforming ortho-position and terminal-position benzene rings on the intermediate benzene rings of bifenthrin; and the novel bifenthrin derivatives have excellent insecticidal and mosquito-killing effect on both larvae and adult mosquitoes, are significantly reduced in toxicity and improved in metabolic stability, and shows good application prospects.

Description

technical field [0001] The invention belongs to the technical field of pesticides for structure modification of medicine small molecules. More specifically, it relates to a novel bifenthrin derivative and its preparation method and application. Background technique [0002] At present, blood-sucking adult mosquitoes can transmit many diseases because they bite humans and animals, such as malaria, dengue fever, filariasis, Japanese encephalitis and other intermediate hosts of more than 80 pathogens. 100% of the population on all continents except Antarctica can be exposed to mosquitoes. Blood-sucking mosquitoes not only have a serious impact on people's daily life, study and work, but more importantly, mosquitoes are the spread of the above-mentioned diseases media, can cause a series of health and safety problems. Therefore, for how to carry out effective mosquito control, while playing a good role in killing mosquitoes or repelling mosquitoes, the harm to the human body i...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C61/40C07C51/363C07D333/16C07D333/56C07D333/62A01N43/10A01N43/12A01N53/08A01P7/04
CPCA01N43/10A01N43/12A01N53/00C07C61/40C07D333/16C07D333/56C07D333/62
Inventor 赵肃清张炳杰冯冬燕钟颖颖黄锦渠吴可凌华英谭绮婷陈燕婷赵佳伟马焯霖江政云杨洋朱秋雁洪为谦
Owner GUANGDONG UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com