Application of eight-membered oxygen bridge heterocyclic compound as synergist of bee selective insecticide

A compound and insecticide technology, applied in the field of pesticides, can solve the problem that honeybees do not show selectivity, increase the insecticidal activity of imidacloprid neonicotinoid insecticides, etc.

Pending Publication Date: 2020-05-19
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Neonicotinoid insecticides are selective agonists of insect nicotinic acetylcholine receptors (nAChRs). Due to the characteristics of their mechanism of action, it is difficult for existing synergists to produce synergistic effects on them.
In previous studies, we found that an eight-membered oxygen-bridged heterocyclic compound (IPPA08) can significantly increase the insecticidal activity of neonicotinoid insecticides such as imidacloprid, thiacloprid, and thiamethoxam, but its effect on honey bees Shown no selectivity

Method used

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  • Application of eight-membered oxygen bridge heterocyclic compound as synergist of bee selective insecticide
  • Application of eight-membered oxygen bridge heterocyclic compound as synergist of bee selective insecticide
  • Application of eight-membered oxygen bridge heterocyclic compound as synergist of bee selective insecticide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1: 1-(4-methylphenyl)-10-nitro-1,2,3,5,6,7,8,9-octahydro-5,9-epoxyimidazo[1, Synthesis of 2-a] azacyclooctene

[0067]

[0068] At room temperature, 1-(4-methylphenyl)-2-(nitromethylene) imidazolidine (1.165g, 5mmol) and 50% glutaraldehyde aqueous solution (1.2g, 6mmol) were dissolved in 20mL without Add a catalytic amount of concentrated hydrochloric acid (0.1 mL) to water acetonitrile and stir to react, followed by TLC. After the reaction, saturated NaHCO 3 The pH of the aqueous solution was adjusted to neutral, extracted with dichloromethane (20mL×3), the organic phase was collected and washed with anhydrous Na 2 SO 4 Drying, concentration, and separation by column chromatography yielded a light yellow powdery pure product with a yield of 80%; m.p.122.9-124.1°C; 1 H NMR (400MHz, CDCl 3 )δ7.18(dd,J=15.6,7.8Hz,4H),5.37–5.29(m,1H),4.96(d,J=14.8Hz,1H),4.83(d,J=14.8Hz,1H), 3.75–3.64(m,1H),3.63–3.45(m,4H),2.34(s,3H),2.16(d,J=13.6Hz,1H),1.94–1.83(m,2H),1.64...

Embodiment 2

[0069] Example 2: 1-(4-isopropylphenyl)-10-nitro-1,2,3,5,6,7,8,9-octahydro-5,9-epoxyimidazo[1 ,Synthesis of 2-a]azacyclooctene

[0070]

[0071] At room temperature, 1-(4-isopropylphenyl)-2-(nitromethylene) imidazolidine (1.305g, 5mmol) and 50% glutaraldehyde aqueous solution (1.2g, 6mmol) were dissolved in 20mL In anhydrous acetonitrile, a catalytic amount of concentrated hydrochloric acid (0.1 mL) was added to stir the reaction, followed by TLC. After the reaction, saturated NaHCO 3 The pH of the aqueous solution was adjusted to neutral, extracted with dichloromethane (20mL×3), the organic phase was collected and washed with anhydrous Na 2 SO 4 Drying, concentration, and separation by column chromatography gave a pure yellow powder with a yield of 83%; m.p.140.2-141.3°C; 1 H NMR (400MHz, DMSO-d 6 )δ7.34–7.14(m,4H),5.07-5.03(m,2H),4.96(d,J=15.0Hz,1H),4.75(d,J=15.0Hz,1H),3.76–3.54(m ,4H),2.94–2.80(m,1H),1.83–1.44(m,6H),1.19(d,J=6.8Hz,6H)ppm. 13 C NMR (101MHz, DMSO-d 6...

Embodiment 3

[0072] Example 3: 1-(4-ethylphenyl)-10-nitro-1,2,3,5,6,7,8,9-octahydro-5,9-epoxyimidazo[1, Synthesis of 2-a] azacyclooctene

[0073]

[0074] At room temperature, 1-(4-ethylphenyl)-2-(nitromethylene) imidazolidine (1.235g, 5mmol) and 50% glutaraldehyde aqueous solution (1.2g, 6mmol) were dissolved in 20mL without Add a catalytic amount of concentrated hydrochloric acid (0.1 mL) to water acetonitrile and stir to react, followed by TLC. After the reaction, saturated NaHCO 3 The pH of the aqueous solution was adjusted to neutral, extracted with dichloromethane (20mL×3), the organic phase was collected and washed with anhydrous Na 2 SO 4 Drying, concentration, and separation by column chromatography gave a pure yellow powder with a yield of 90%; m.p.118.9-119.1°C; 1 H NMR (400MHz, CDCl 3 )δ7.18(dd,J=15.6,7.8Hz,4H),5.37–5.29(m,1H),4.96(d,J=14.8Hz,1H),4.83(d,J=14.8Hz,1H), 3.75–3.64(m,1H),3.63–3.45(m,4H),2.34(s,3H),2.16(d,J=13.6Hz,1H),1.94–1.83(m,4H),1.64–1.62( m,3H)ppm. 1...

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Abstract

The invention discloses an application of an eight-membered oxygen bridge heterocyclic compound as a synergist of a bee selective insecticide. The structure of the eight-membered oxygen bridge heterocyclic compound is as shown in a formula I, and the definition of each substituent group in the formula is as shown in the specification and claims. The eight-membered oxygen bridge heterocyclic compound as shown in the formula I can significantly increase the insecticidal effect of the insecticide, shows selectivity to bees, and does not increase the toxicity of the insecticide to bees.

Description

technical field [0001] The invention relates to the field of pesticides. Specifically, the present invention relates to a new use of an eight-membered oxygen-bridged heterocyclic compound containing a benzene ring structure that is selective for honeybees as a synergist for neonicotinoid insecticides and other insecticides. Background technique [0002] In the mid-1980s, Bayer developed the first neonicotinoid insecticide, imidacloprid, and became one of the most successful new insecticides. High activity, wide insecticidal spectrum, low toxicity to mammals and aquatic animals, good systemicity, appropriate field stability and environmental friendliness have become an important hotspot for the creation of new pesticides. Subsequently, a series of neonicotinoid insecticides such as thiacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram and dinotefuran were successively developed. However, the long-term and large-scale use of a single type of insecticide has led to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/90C07D498/18A01N51/00A01N47/18A01N43/707A01N57/16A01P7/04
CPCA01N43/90A01N51/00A01N47/18A01N43/707A01N57/16C07D498/18
Inventor 李忠徐晓勇张晓王轶平刘泽文邵旭升须志平程家高
Owner EAST CHINA UNIV OF SCI & TECH
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