Dialdehyde-built nitrogen-containing or oxygen-containing heterocyclic compound with insecticidal activity and preparation method thereof

A compound and composition technology, applied in the field of new neonicotinoid insecticides, can solve the problems of narrow insecticidal spectrum, limited drug selectivity, restricted compound development, etc., so as to solve the problem of resistance and expand the insecticidal spectrum. Effect

Active Publication Date: 2014-01-22
EAST CHINA UNIV OF SCI & TECH
View PDF11 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, due to the serious resistance problem caused by the excessive and frequent use of imidacloprid and the cross-resistance between neonicotinoid insecticides due to structural similarity, the application of this type of compound is limited to a certain extent, and this type of insecticide is restricted. At the same time, neonicotinoid insecticides are mainly effective against homopteran and coleopteran pests, and their relatively narrow insecticidal spectrum also limits the selectivity of insecticides in pest control

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
  • Dialdehyde-built nitrogen-containing or oxygen-containing heterocyclic compound with insecticidal activity and preparation method thereof
  • Dialdehyde-built nitrogen-containing or oxygen-containing heterocyclic compound with insecticidal activity and preparation method thereof
  • Dialdehyde-built nitrogen-containing or oxygen-containing heterocyclic compound with insecticidal activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0061] The preparation method of the compound of the present invention

[0062] The compounds of the present invention can be synthesized by the reaction steps described above. Those skilled in the art can synthesize the compound of formula (a) in the reaction step according to the prior art documents, for example, refer to WO2006056108A1, WO2007101369A1 and PCT / CN2008 / 071115.

[0063] In a specific embodiment of the present invention, the synthetic method of formula (A) compound is as follows:

[0064]

[0065] In a specific embodiment of the present invention, the synthetic method of formula (B) compound is as follows:

[0066]

[0067] In a specific embodiment of the present invention, the synthetic method of formula (C) compound is as follows:

[0068]

[0069] In a specific embodiment of the present invention, the synthetic method of formula (C) compound is as follows:

[0070]

[0071] In one embodiment of the present invention, the compound of formula (...

Embodiment 1

[0105] Example 1 : 4-(1-((6-chloropyridin-3-yl)methyl)-4,5-dihydro-1H-imidazolidin-2-yl)-1-(1-((6-chloropyridine- Synthesis of 3-yl)methyl)imidazolidin-2-yl)-1,4-dinitro-3-buten-2-ol (compound 13)

[0106] Using 0.03mol of 2-chloro-5-chloromethylpyridine as a starting material, prepare 2-chloro-5-(2-nitromethylene-imidazolidin-1-ylmethanol according to the method described in WO2006056108A1 and WO2007101369A1 base)-pyridine, the yield was 56%; Rf = 0.46 (petroleum ether: ethyl acetate = 1:1); mp = 156.9°C-161.8°C. GC MS (m / s) 220(25), 126(100), 90(9).

[0107] 4-(1-((6-chloropyridin-3-yl)methyl)-4,5-dihydro-1H-imidazolidin-2-yl)-1-(1-((6-chloropyridine-3 -base) Synthesis of Methyl)imidazolidin-2-yl)-1,4-Dinitro-3-buten-2-ol

[0108]

[0109]Add 1.27g (0.005mol) of 2-chloro-5-(2-nitromethylene-imidazolidin-1-ylmethyl)-pyridine, 30ml of anhydrous acetonitrile, and 3ml of 30% glyoxal aqueous solution to 50ml In a round-bottomed flask, stir for half an hour, then add ...

Embodiment 2

[0111] Example 2 : 2-chloro-5-((-2-(-4-(1-((6-chloropyridin-3-yl)methyl)-4,5-dihydro-1H-imidazolidin-2-yl) Synthesis of -2-methoxy-1,4-dinitro-3-butenyl)imidazolidin-1-yl)methyl)pyridine (compound 14)

[0112]

[0113] Add 0.549g (0.001mol) of compound 1 into a 50ml round-bottomed flask, then add 10ml of methanol, 50ml of dichloromethane and a catalytic amount of concentrated hydrochloric acid, reflux, and track the reaction by TLC. After the reaction was completed, the solvent was removed, and the pure product was obtained as a yellow powder through column chromatography separation, with a yield of 62%.

[0114] mp=151.6-153.1℃; 1 H NMR (400Mz, DMSO-d 6 ):δ9.03(s,1H),8.38(d,J=2.0Hz,1H),8.36(d,J=2.0Hz,1H),7.81-7.85(m,2H),7.49-7.51(m, 2H),6.50(d,J=7.2Hz,1H),5.35(d,J=15.2Hz,1H),5.19(d,J=15.2Hz,1H),4.80(d,J 1 =7.2Hz,1H),4.77(d,J=16.8Hz,1H),4.69(d,J=16.8Hz,1H),3.68(s,3H),3.88-3.95(m,2H),3.61-3.85 (m,5H),3.38-3.41(m,1H)ppm; 13 C NMR (100Mz, DMSO-d 6 ): δ162.6, 158.7, 14...

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 relates to preparation and application of a dialdehyde-built nitrogen-containing or oxygen-containing heterocyclic compound with the insecticidal activity, provides a compound with the structure represented by formulas (A), (B), (C) or (D) or an optical isomer and a cis-trans-isomer of the compound or agriculturally and pharmacologically acceptable salt and also relates to an agricultural combination comprising the compound or the optical isomer and the cis-trans-isomer of the compound or the agriculturally and pharmacologically acceptable salt, application of the agricultural combination and a preparation method for the compound or the optical isomer and the cis-trans-isomer of the compound or the agriculturally and pharmacologically acceptable salt. The compound and derivatives thereof are high in insecticidal activity to homoptera, lepidoptera and other types of agroforestry pests such as aphids, plant hoppers, aleyrodids, leafhoppers, thrips, cotton bollworms, cabbage caterpillars, plutella xylostella, prodenia litura and armyworms.

Description

[0001] This application is a divisional case of an invention patent application with an application date of December 19, 2008, an application number of 200810207355.2, and an invention title of "Nitrogen-containing or oxygen-containing heterocyclic compounds with insecticidal activity constructed by dialdehyde and its preparation method" Apply. technical field [0002] The invention relates to a novel neonicotinoid insecticide, a preparation method and application thereof. Background technique [0003] Neonicotinoid insecticides represented by imidacloprid have high insecticidal activity, wide insecticidal spectrum, low toxicity to mammals and aquatic animals, good system properties, appropriate field stability and environmental friendliness, and become An important hot spot for the creation of new pesticides. A series of neonicotinoid insecticides such as thiacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram, dinotefuran and the like have been developed successi...

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): A01N43/90A01N43/50A01N43/40A01N43/78A01N43/54C07D491/08C07D491/18C07D401/14C07D417/14C07D213/61A01P7/04
Inventor 李忠钱旭红邵旭升徐晓勇陶黎明宋恭华
Owner EAST CHINA UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap