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

Phenylpyrazole zwitterionic compound and application thereof in control of resistant pests

A phenylpyrazole, zwitterion technology, applied in the application, pesticide, organic chemistry and other directions, can solve the problems such as the ineffectiveness of resistant pests, increase water solubility, etc., to increase the spectrum of pest control and overcome resistance , the effect of high yield

Active Publication Date: 2017-11-24
SOUTH CHINA AGRI UNIV
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with commercial benzopyrazole insecticides, this patent has greatly increased water solubility and reduced toxicity to humans, livestock, aquatic organisms and bees. However, toluene is used as a solvent in the process of preparing compounds in this patent. The use of strong base sodium hydride as protonation reagent is still lacking in environmental friendliness
In particular, the compounds prepared by this patent do not show significant efficacy against resistant pests

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
  • Phenylpyrazole zwitterionic compound and application thereof in control of resistant pests
  • Phenylpyrazole zwitterionic compound and application thereof in control of resistant pests
  • Phenylpyrazole zwitterionic compound and application thereof in control of resistant pests

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The preparation of embodiment 1 phenylpyrazole zwitterionic compound

[0037] Preparation method: Add 4.40g (0.01mol) of fipronil to a 100mL three-necked flask equipped with a magnetic stirrer, a drying tube and a dropping funnel, add 40mL of dry DMF, stir to dissolve, and then add 2.76g of anhydrous potassium carbonate ( 0.02mol), add 1.78mL 98% bromoacetyl bromide dropwise, stir at room temperature for 30min, then add quinoline (0.012mol) dissolved in DMF, stir overnight at room temperature until the reaction is complete, quench with ice water, extract with ethyl acetate , the organic phase was dried with anhydrous sodium sulfate, and the filtrate was filtered, then subjected to column chromatography after vacuum distillation, and recrystallized from methanol / petroleum ether to obtain yellow crystals with a yield of 62.40%, m.p.103-105°C. The detection data is:

[0038] 1 H NMR (600MHz, DMSO) δ9.24 (dd, J = 5.8, 1.3Hz, 1H, Ar-H), 8.96 (d, J = 8.3Hz, 1H, Ar-H), 8.23 ...

Embodiment 2

[0044] Preparation of embodiment 2 phenylpyrazole zwitterionic compounds

[0045] The preparation method is the same as in Example 1, wherein the molar ratio of fipronil: bromoacetyl bromide: 5-aminoquinoline: anhydrous potassium carbonate is 1:1.1:1.2:1.8. Recrystallization from methanol / petroleum ether gave red crystals with a yield of 45.6%, m.p.258-265°C. The detection data is:

[0046] 1H NMR (600MHz, DMSO) δ9.11(d, J=8.5Hz, 1H), 9.02–8.98(m, 1H), 7.87(d, J=1.4Hz, 1H, Ar-H), 7.80(d, J=1.5Hz, 1H, Ar-H), 7.70(t, J=8.3Hz, 1H), 7.56(dd, J=8.5, 5.8Hz, 1H), 7.00(s, 2H, NH 2 ),6.97(d,J=8.7Hz,1H),6.91(d,J=8.0Hz,1H),5.30(dd,J=35.7,16.3Hz,2H,CH 2 ).

[0047] 13 C NMR(151MHz,DMSO)δ168.59,151.86,149.43,148.86,141.63,139.97,137.51,137.27,135.32,135.15,132.06,125.92,125.29,123.54,121.76,119.01,117.05,113.20,110.09,103.93,102.16,99.97 ,62.10.

[0048] HRMS(ESI-TOF):Extract mass calculated for C 23 h 12 Cl 2 f 6 N 6 o 2 S requires[M+H] + 621.0109, found 621.0096; [M+Na] + ...

Embodiment 3

[0052] Preparation of embodiment 3 phenylpyrazole zwitterionic compounds

[0053] The preparation method is the same as in Example 1, wherein the molar ratio of fipronil:bromoacetyl bromide:N,N-dimethyl-5-aminoquinoline:anhydrous potassium carbonate is 1:1.2:1.3:2.3. Recrystallization from methanol / petroleum ether gave red crystals with a yield of 15.52%, m.p.245-249°C. The detection data is:

[0054] 1 H NMR (600MHz, DMSO) δ9.15 (dd, J = 5.8, 1.3Hz, 1H), 8.94 (d, J = 8.5Hz, 1H), 7.93–7.89 (m, 1H), 7.85 (d, J = 1.4Hz, 1H, Ar-H), 7.80(d, J=1.5Hz, 1H, Ar-H), 7.77(dd, J=8.6, 5.7Hz, 1H), 7.52(d, J=8.9Hz, 1H ), 7.34(d, J=7.9Hz, 1H), 5.46(dd, J=34.5, 16.4Hz, 2H, CH 2 ),2.95(s,6H,CH 3 ,CH 3 ).

[0055] 13 C NMR(151MHz,DMSO)δ168.45,152.81,151.71,149.58,143.29,140.52,137.47,135.94,135.26,135.11,132.22,125.88,125.32,124.27,123.57,121.77,119.52,116.49,113.16,111.49,85.91,75.89 ,62.24,45.43.

[0056] HRMS(ESI-TOF):Extract mass calculated for C 25 h 16 Cl 2 f 6 N 6 o 2 S re...

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 a phenylpyrazole zwitterionic compound and application thereof in control of resistant pests. The phenylpyrazole zwitterionic compound belongs to a dipolar compound containing positive and negative charges in a delocalization state in the structure, and a molecule contains a pharmacophore phenylpyrazole group of a gamma-aminobutyric acid receptor and a zwitterionic group of a nicotinic acetylcholine receptor that are used for acting on a nerve parts of an insect, so that compared with a single phenylpyrazole insecticide acting on the gamma-aminobutyric acid receptor of the insect, the phenylpyrazole zwitterionic compound are used for simultaneously acting on two different target spots of the nerve part of the insect, synergistic interaction can be achieved, the purpose of overcoming resistance is achieved, and the high efficiency of the phenylpyrazole zwitterionic compound for resistant pests is showed; and in addition, a control spectrum can be added, and therefore, the application prospect is very wide.

Description

technical field [0001] The present invention relates to phenylpyrazole zwitterionic compounds and their application in the control of resistant pests. Background technique [0002] Fipronil (fipronil), the first phenylpyrazole insecticide developed by the French company Rhône-Planck in 1989, was registered for use in my country for the first time in 1992. The target of fipronil is the GABA receptor in insects, and it mainly acts on the synaptic area where nerve endings and muscles connect. Under normal circumstances, the GABA receptor in the insect body is activated, and the chloride ion channel in the binding site of GABA is opened accordingly, causing chloride ions to flow into the post-synaptic membrane of the nerve, promoting the polarization effect of the action potential, and making the entire insect nervous system active. sequence operation. Fipronil interferes with the opening function of the chloride ion channel, resulting in the local loss of insect GABA receptor...

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
IPC IPC(8): C07D401/12C07D231/44C07D403/12A01N47/02A01P7/04
CPCA01N47/02C07D231/44C07D401/12C07D403/12
Inventor 江定心付春伶杨小东陈燕飞费程程
Owner SOUTH CHINA AGRI UNIV
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