Bicyclic neonicotine compounds constructed by cycloalkenone, and preparation method and application thereof

A compound and reaction technology, applied in the field of new neonicotinoid pesticides, can solve problems such as affecting the development prospects of pesticides

Inactive Publication Date: 2014-02-12
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above factors have seriously affected the development prospects of this type of insecticide

Method used

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  • Bicyclic neonicotine compounds constructed by cycloalkenone, and preparation method and application thereof
  • Bicyclic neonicotine compounds constructed by cycloalkenone, and preparation method and application thereof
  • Bicyclic neonicotine compounds constructed by cycloalkenone, and preparation method and application thereof

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preparation example Construction

[0064] The preparation method of the compound of the present invention

[0065] The compounds of the present invention can be synthesized by the reaction steps described above. Those skilled in the art can synthesize intermediates in the reaction steps according to prior art documents, for example, refer to WO2006056108A1, WO2007101369A1 and PCT / CN2008 / 071115.

[0066] The preparation method of the compound of the present invention can be the preparation method commonly used in this field, and the present invention provides a kind of preferred preparation method of the compound shown in general formula (A), comprising:

[0067] (i) said method comprises the steps: in an inert solvent (such as acetonitrile or 1,4-dioxane), in the presence of a catalytic amount of acid (such as glacial acetic acid), combining the compound of formula (a) with the compound of formula (b ) compound is reacted for a period of time (such as 2-48 hours or 20-30 hours), thereby obtaining the compoun...

Embodiment 1

[0090] Embodiment 1. Synthesis of compound 1

[0091]

[0092] Add 5mmol 2-chloro-5-(2-nitromethylene-imidazolidin-1-ylmethyl)-pyridine, 30mL anhydrous acetonitrile, and 6mmol cyclopentenone into a 50mL round bottom flask, stir for half a Hours, then add 3 drops of glacial acetic acid catalyst, reflux and stir for 24 hours. The solvent was spin-dried, and column chromatography (dichloromethane:methanol=10:1) gave 0.36 g of a light yellow powdery solid, with a yield of about 21%.

[0093] 1 H NMR (400Mz, CDCl 3 ):δ8.33(d,J=2.4Hz,1H),7.56(dd,J=8.6Hz,J=2.4Hz,1H),7.41(d,J=8.6Hz,1H),4.52(d,J =15.2Hz,1H),4.43(d,J=15.2Hz,1H),3.85-3.90(m,2H),3.67-3.71(m,1H),3.46-3.51(m,1H),3.30-3.34( m, 1H), 1.99-2.56(m, 6H), 1.20-1.21(m, 1H); HRMS(ES+) calculated value C 15 h 18 N 4 o 3 35 Cl(M+H)+, 337.1067; Found, 337.1059.

Embodiment 2

[0094] Embodiment 2. Synthesis of compound 2

[0095]

[0096]Add 1mmol of compound 1 into a 50mL round bottom flask, 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%.

[0097] 1 H NMR (400Mz, CDCl 3 ):δ8.35(d,J=2.5Hz,1H),7.58(dd,J=8.6Hz,J=2.5Hz,1H),7.42(d,J=8.6Hz,1H),4.54(d,J =15.0Hz,1H),4.48(d,J=15.0Hz,1H),3.85-3.91(m,2H),3.70-3.72(m,1H),3.48-3.51(m,1H),2.14-2.56( m,6H),1.20-1.21(m,1H),1.09(s,3H);

[0098] HRMS(ES+) calculated value C 16 h 20 N 4 o 3 35 Cl(M+H)+, 351.1224; Found, 351.1221.

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Abstract

The invention relates to bicyclic neonicotine compounds constructed by cycloalkenone, and a preparation method and an application thereof, concretely provides compounds having a structure represented by formula (A) or optical isomers, cis-trans-isomers or pharmaceutically acceptable salts of the compounds, and a preparation method and a use thereof, and also relates to an agricultural composition containing the compounds or the optical isomers, cis-trans-isomers or pharmaceutically acceptable salts thereof, and a use thereof. The compounds have a high insecticidal activity against agriculture and forestry pests comprising homoptera pests, lepidoptera pests and the like, such as aphids, plant hoppers and whiteflies.

Description

technical field [0001] The invention relates to a novel neonicotinoid insecticide, a preparation method and application thereof. Background technique [0002] The discovery of neonicotinoid insecticides is considered a milestone in the development of the field of agricultural chemistry in the past two decades. This kind of insecticide is an agonist of insect nicotinic acetylcholine receptor, acts on the central nervous system of insects, has high efficiency, low toxicity, and environmental friendliness, and is a hot field of green pesticide creation. Since the launch of imidacloprid by German Bayer in the early 1990s, six neonicotinoid insecticides, including nitenpyram, acetamiprid, thiamethoxam, thiacloprid, clothianidin, and dinotefuran, have been commercialized one after another. It is currently the most important chemical insecticide variety, registered in more than 120 countries, with annual global sales of more than 2.5 billion US dollars, and a market share of more ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/08C07D401/12C07D417/12C07D405/12A01N43/90A01N43/46A01N43/78A01P7/04
CPCA01N43/42A01N43/78A01N43/90C07D401/12C07D405/12C07D417/12C07D471/08
Inventor 田忠贞徐晓勇须志平李忠崔书霞邵旭升
Owner EAST CHINA UNIV OF SCI & TECH
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