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Derivative of tetrahydroindeno-6-vinyl-1,3a-diazapentalene and preparation method and application thereof

A technology of rozimidazole and its derivatives, which is applied in the field of derivatives of tetrahydroindenopyrrozimidazole and its preparation and application, and can solve the problem of restricting insect pest control drug selectivity, narrow insecticidal spectrum, and narrow insecticidal spectrum of resistance And other issues

Inactive Publication Date: 2015-11-04
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the frequent and excessive use of neonicotinoid insecticides will inevitably lead to environmental and ecological problems such as resistance and bee toxicity, which restricts the use of such compounds. Pests, whose relatively narrow insecticidal spectrum also limits the choice of insecticides in pest control
[0004] Therefore, rational molecular design and structural modification are carried out to produce new and more effective insecticides, to solve the problems of neonicotinoid insecticide resistance, bee toxicity and narrow insecticidal spectrum, so that they can be applied to insecticides Agent becomes the technical problem that the present invention needs to solve

Method used

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  • Derivative of tetrahydroindeno-6-vinyl-1,3a-diazapentalene and preparation method and application thereof
  • Derivative of tetrahydroindeno-6-vinyl-1,3a-diazapentalene and preparation method and application thereof
  • Derivative of tetrahydroindeno-6-vinyl-1,3a-diazapentalene and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062]1-((6-Chloropyridin-3-yl)methyl)-4a,9a-dihydroxy-10-nitro-2,3,4a,9a-tetrahydroindene[2',1':4,5 Synthesis of ]pyrrole[1,2-a]imidazol-9(1H)-one (Compound Ⅰ-1)

[0063]

[0064] 1.27g (0.005mol) of 2-chloro-5-(2-nitromethylene-imidazolidin-1-ylmethyl)-pyridine, 30ml of anhydrous methanol, 0.890g (0.005mol) of indene hydrate Triketones were placed in a 100ml round bottom flask. Stir at room temperature, and follow the reaction by TLC until the raw material point disappears. The reaction was stopped and filtered to obtain 1.863 g of solid (compound I-1), with a yield of 90%.

[0065] 1 H NMR (400MHz, DMSO-d 6 )δ8.34(s,1H),7.89–7.71(m,4H),7.66(t,J=6.9Hz,1H),7.52(d,J=8.0Hz,1H),7.09(s,1H), 6.43(s,1H),5.09(dd,J=249.9,15.4Hz,2H),4.02–3.71(m,3H),3.72–3.49(m,1H)ppm.

[0066] 13 C NMR (100MHz, DMSO-d 6 )δ196.56,156.75,150.02,149.62,146.44,139.70,136.25,134.70,132.43,131.18,125.62,124.73,124.36,104.25,89.13,86.52,54.47,08.0701,4

[0067] HRMS(ES+) calculated value C 19 h ...

Embodiment 2

[0070] 1-((6-Chloropyridin-3-yl)methyl)-4a,9b-dihydroxy-10-nitro-2,3,4a,9b-tetrahydroindene[1',2':4,5 Synthesis of ]pyrrole[1,2-a]imidazol-5(1H)-one (Compound Ⅰ-2)

[0071]

[0072] 0.414g (0.001mol) of 1-((6-chloropyridin-3-yl)methyl)-4a,9a-dihydroxy-10-nitro-2,3,4a,9a-tetrahydroindene[2 ',1': 4,5]pyrrole[1,2-a]imidazol-9(1H)-one, 10ml of dichloromethane, placed in a 25ml round bottom flask. Stir under reflux conditions, and follow the reaction by TLC until the raw material point disappears. The reaction was stopped, and the product was separated by silica gel column chromatography (pure ethyl acetate as eluent) to obtain 0.311 g of white solid (Compound I-2), with a yield of 75%.

[0073] 1 H NMR (400MHz, DMSO-d 6 )δ8.36(s,1H),8.28(d,J=7.8Hz,1H),7.84(t,J=7.5Hz,1H),7.81–7.71(m,2H),7.59(t,J=7.4 Hz,1H),7.51(d,J=8.2Hz,1H),7.10(s,1H),6.44(s,1H),5.11(dd,J=251.7,15.5Hz,2H),3.97–3.79(m ,2H),3.71(dd,J=17.6,9.7Hz,1H),3.56(dd,J=17.5,9.5Hz,1H)ppm.

[0074] 13 C NMR (100MHz, D...

Embodiment 3

[0078] 1-((6-chloropyridin-3-yl)methyl)-9b-hydroxy-4a-methoxy-10-nitro-2,3,4a,9b-tetrahydroindene[1',2': Synthesis of 4,5]pyrrole[1,2-a]imidazol-5(1H)-one (compound Ⅰ-3):

[0079]

[0080] 0.414g (0.001mol) of 1-((6-chloropyridin-3-yl)methyl)-4a,9b-dihydroxy-10-nitro-2,3,4a,9b-tetrahydroindene[1 ',2': 4,5]pyrrole[1,2-a]imidazol-5(1H)-one, 10ml of anhydrous tetrahydrofuran, placed in a 25ml round bottom flask. Add 0.036g (0.0015mol) NaH, stir at room temperature until the gas is no longer released, then add enough methyl iodide, and follow the reaction by TLC until the raw material point disappears. The reaction was stopped and evaporated to dryness. The crude product was separated by silica gel column chromatography (pure ethyl acetate as eluent) to obtain 0.364 g of white solid (Compound I-3), with a yield of 85%.

[0081] 1 H NMR (400MHz, DMSO-d 6 )δ8.35(s,1H),8.27(d,J=7.7Hz,1H),7.87(t,J=7.3Hz,1H),7.77(d,J=7.0Hz,2H),7.60(t, J=7.2Hz, 1H), 7.51(d, J=8.0Hz, 1H), 6.66(s,...

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Abstract

The invention relates to a derivative of tetrahydroindeno-6-vinyl-1,3a-diazapentalene and a preparation method and application thereof. Based on the nitromethylene structure of an existing nitromethylene-neonicotine insecticide, substituted or non-substituted ninhydrin reacts with a nitromethylene-compound (or other analogs), and then the novel-structure derivative of tetrahydroindeno-6-vinyl-1,3a-diazapentalene is synthesized. Testing results show that the derivative has remarkable insecticidal activity and a wide insecticidal spectrum.

Description

technical field [0001] The invention relates to a derivative of tetrahydroindenopyrroloimidazole and its preparation method and application. 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. Later, a series of neonicotinoid insecticides such as thiacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram, and dinotefuran were developed successively (European patents 247477, 296453, 685477, 235725, 235725 , 315826, 192060, 244777, 0386565, 580553 and 1031566, Japanese patents 62292765, 8259568, 8291171 and 7242633). [0003] However, the frequent and excessive use of neonicotinoid insecticides will inevitably lead to environmental and ecological problems such as resistance and bee ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P7/04
CPCA01N43/90C07D487/04
Inventor 邵旭升李忠陈南阳徐晓勇须志平程家高
Owner EAST CHINA UNIV OF SCI & TECH