Dialdehyde-built disinsection activity-having nitrogen or oxygen-containing heterocyclic compound and preparation method

一种化合物、六元杂环的技术，应用在新型新烟碱类的杀虫剂领域，能够解决窄杀虫谱、限制用药选择性、制约化合物发展等问题，达到解决抗性问题、扩大杀虫谱的效果

Active Publication Date: 2010-06-23
EAST CHINA UNIV OF SCI & TECH
View PDF13 Cites 48 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 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 has been 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 disinsection activity-having nitrogen or oxygen-containing heterocyclic compound and preparation method
  • Dialdehyde-built disinsection activity-having nitrogen or oxygen-containing heterocyclic compound and preparation method
  • Dialdehyde-built disinsection activity-having nitrogen or oxygen-containing heterocyclic compound and preparation method

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0060] The preparation method of the compound of the present invention

[0061] 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 literature, for example, refer to WO 2006056108A1, WO 2007101369A1 and PCT / CN2008 / 071115.

[0062] In a specific embodiment of the present invention, the synthetic method of formula (A) compound is as follows:

[0063] (R 2 for hydrogen).

[0064] In a specific embodiment of the present invention, the synthetic method of formula (B) compound is as follows:

[0065]

[0066] In a specific embodiment of the present invention, the synthetic method of formula (C) compound is as follows:

[0067]

[0068] In a specific embodiment of the present invention, the synthetic method of formula (C) compound is as follows:

[0069]

[0070] In one embodiment of the present invention, t...

Embodiment 1

[0104] 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)

[0105] Using 0.03mol of 2-chloro-5-chloromethylpyridine as a starting material, prepare 2-chloro-5-(2-nitromethylene-imidazolidine-1- Methyl)-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).

[0106] 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

[0107]

[0108]Add 1.27g (0.005mol) of 2-chloro-5-(2-nitromethylene-imidazolidin-1-ylmethyl)-pyridine, 30ml of anhydrous acetonitrile, and 3ml of 30% aqueous glyoxal In a 50ml round-bottomed flask, stir for half an hour, then add a catalytic amount of concentrated hydrochloric acid to catalyze, continue to stir, TLC to track...

Embodiment 2

[0110] 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)

[0111]

[0112] 0.549g (0.001mol) of compound 1 was added to a 50ml round bottom flask, and then 10ml of methanol, 50ml of dichloromethane and a catalytic amount of concentrated hydrochloric acid were added, refluxed, and the reaction was tracked by TLC. After the reaction was finished, the solvent was removed, and the pure product was obtained as a yellow powder through column chromatography separation, with a yield of 62%.

[0113] mp=151.6-153.1°C; 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 (...

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 the preparation and the use of a dialdehyde-built disinsection activity-having nitrogen or oxygen-containing heterocyclic compound, and provides a compound with a chemical formula showed as formula (A), (B), (C) or (D), or an optical isomer, a cis-trans isomer, or an agriculturally pharmaceutically acceptable salt of the compound,. The invention further relates to an agricultural composite which comprises the compound, or the optical isomer the cis-trans isomer of the compound, or the agriculturally pharmaceutically acceptable salt, the use of the agricultural composite, and a preparation method of the compound, or the optical isomer, the cis-trans isomer of the compound, or the agriculturally pharmaceutically acceptable salt. The compound and ramification thereof has high disinsection activity for agriculture and forestry injurious pests such as aphid, plant hopper, leafhopper, thrips palmi karny, cotton bollworm, cabbage caterpillar, plutella xylostella, prodenia litura and armyworm, etc.

Description

technical field [0001] The invention relates to a novel neonicotinoid insecticide, a preparation method and application thereof. Background technique [0002] 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 successively afterwards (seeing European patents 247477, 296453, 685477, 235725, 235725, 315826, 192060, 244777, 0386565, 580553 and 1031566, Japanese patents 62292765, 8259568, 8291171 and 7242633). [0003] However, due to the serious resistance problem caused by the excessive and frequent use of imidacloprid and the cross-resistance between neonicotin...

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): C07D401/14C07D213/61C07D417/14C07D498/08C07D498/18A01N43/90A01N43/78A01N43/50A01P7/00
CPCA01N43/50C07D491/18A01N43/62A01N43/90C07D213/61C07D409/14C07D498/08C07D413/12C07D401/14C07D401/12C07D417/14C07D405/14A01N43/78A01N43/54C07D471/14A01N43/40C07D498/18A01N33/02
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