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Dialdehyde-constructed nitrogen- 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, and restricting the development of compounds, so as to expand the insecticidal spectrum and solve the problem of resistance Effect

Active Publication Date: 2017-04-26
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 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

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

Examples

Experimental program
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preparation example Construction

[0062] The preparation method of the compound of the present invention

[0063] 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.

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

[0065]

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

[0071]

[0072] In one embodiment of the present invention, the compound of formul...

Embodiment 1

[0106] 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)

[0107] Using 0.03mol of 2-chloro-5-chloromethylpyridine as a starting material, 2-chloro-5-(2-nitromethylene-imidazolidin-1-yl was prepared according to the methods described in WO 2006056108A1 and WO2007101369A1 Methyl)-pyridine, the yield is 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).

[0108] 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

[0109]

[0110] 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 c...

Embodiment 2

[0112] 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)

[0113]

[0114] 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%.

[0115] 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(m,1H)ppm; 13 C NMR (100Mz...

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Abstract

The invention relates to a dialdehyde-constructed nitrogenous or heterocyclic oxygen compound with insecticidal activity, and preparation and application thereof, and provides a compound disclosed as Formula (A), (B), (C) or (D), or an optical isomer, cis-trans-isomer or insecticidally acceptable salt thereof. The invention also relates to an agricultural composition comprising the compound or the optical isomer, cis-trans-isomer or insecticidally acceptable salt thereof, application of the agricultural composition, and a preparation method of the compound or the optical isomer, cis-trans-isomer or insecticidally acceptable salt thereof. The compound and derivatives thereof have high insecticidal activity for Homoptera, Lepidoptera and other pests in agriculture and forestry, such as aphids, planthoppers, aleyrodids, leafhoppers, thrips, cotton bollworms, cabbage worms, cabbage moths, tobacco caterpillars, armyworms and the like.

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 201310398752.3, and an invention title of "Nitrogen-containing or oxygen-containing heterocyclic compounds with insecticidal activity constructed by dialdehyde and its preparation method" Apply. [0002] The application with the application number 201310398752.3 is an invention patent with the application date of December 19, 2008, the application number 200810207355.2, and the invention title "Nitrogen or oxygen-containing heterocyclic compound with insecticidal activity constructed by dialdehyde and its preparation method" Divisional application of the application. technical field [0003] The invention relates to a novel neonicotinoid insecticide, a preparation method and application thereof. Background technique [0004] Neonicotinoid insecticides represented by imidacloprid have high insecticidal activity, wide insectic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/08C07D498/18A01N43/90A01P7/02A01P7/04
CPCA01N43/90C07D498/08C07D498/18
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