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Application of eight-membered oxygen-bridge heterocyclic compound as pesticide synergist

A kind of technology of heterocyclic compound and eight-membered oxygen bridge, applied in the field of pesticides

Active Publication Date: 2016-05-11
NANJING AGRICULTURAL UNIVERSITY +1
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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.
No specific synergist for this type of insecticide has been reported in the literature

Method used

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  • Application of eight-membered oxygen-bridge heterocyclic compound as pesticide synergist
  • Application of eight-membered oxygen-bridge heterocyclic compound as pesticide synergist
  • Application of eight-membered oxygen-bridge heterocyclic compound as pesticide synergist

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Example 1: 1-(4-chlorophenyl)-10-nitro-1,2,3,5,6,7,8,9-octahydro-5,9-epoxyimidazo[1,2 -a] Synthesis of azacyclooctene tetraene (compound 9)

[0091]

[0092] Put 1.27g (0.005mol) of 1-(4-chlorophenyl)-2-(nitromethylene) imidazolidine, 30ml of anhydrous acetonitrile, 3ml of 25% glutaraldehyde aqueous solution, and a catalytic amount of HCl in 50ml in a round bottom flask. Stir at room temperature, and track the reaction by TLC. After the reaction was finished, the solvent was removed, and the pure product was obtained as light yellow powder through column chromatography separation, with a yield of 86%. mp=174.7-175.4°C; 1 HNMR (400Mz, DMSO-d 6):δ7.39(s,306H),7.32(s,307H),4.84(s,308H),4.73(s,154H),4.46(s,158H),3.22(s,80H),3.14(s, 86H), 2.89(s, 87H), 2.84(s, 82H), 1.94(t, J=3.5Hz, 30H), 1.93(s, 148H), 1.77(dd, J=65.0, 60.0Hz, 590H), 1.56(d, J=80.0Hz, 257H), 1.46(d, J=1.6Hz, 6H)ppm; 13 CNMR (100Mz, DMSO-d 6 ): δ167.96, 136.07, 132.68, 129.50, 128.21, 80.05, 64.91...

Embodiment 2

[0093] Example 2: 1-(3-fluoropropyl)-1,2,3,5,6,7,8,9-octahydro-5,9-epoxyimidazolium [1,2-a] nitrogen heterocycle Synthesis of octene-10-carbonitrile (compound 10):

[0094]

[0095] Add 0.845 g (5.0 mmol) of 2-(1-(3-fluoropropyl)imidazoline-2-ylide) acetonitrile and 3 ml of 25% glutaraldehyde aqueous solution into 20 ml of acetonitrile, add a catalytic amount of concentrated hydrochloric acid, stir at room temperature, TLC traced, 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 64%. 1 HNMR (400MHz, DMSO-d 6 )δ4.94(s,8H),5.95–2.81(m,74H),3.23(s,4H),3.10(s,8H),3.41–2.81(m,36H),2.96(d,J=17.4Hz ,14H),2.80(s,4H),1.93(s,6H),1.83(s,9H),1.73(d,J=4.0Hz,14H),1.71–1.46(m,24H)ppm; 13 CNMR (100MHz, DMSO-d 6 ): δ151.48, 120.64, 80.76, 80.05, 65.24, 61.05, 52.63, 49.19, 47.77, 31.54, 30.45, 26.78, 15.74ppm; HRMS(ES+)C 13 h 19 FN 3 O(M+H) + , calculated value: 25...

Embodiment 3

[0096] Example 3: 1-Benzyl-10-nitro-1,2,3,5,6,7,8,9-octahydro-5,9-epoxyimidazo[1,2-a]azepine Synthesis of Cyclooctene (Compound 6)

[0097]

[0098] Put 1.10 g (0.005 mol) of 1-benzyl-2-(nitromethylene) imidazolidine, 30 ml of anhydrous acetonitrile, 3 ml of 25% glutaraldehyde aqueous solution, and a catalytic amount of HCl in a 50 ml round bottom flask . Stir at room temperature, and track the reaction by TLC. After the reaction was finished, the solvent was removed, and the pure product was obtained as light yellow powder through column chromatography separation, with a yield of 66%. mp=154.7-155.4°C; 1 HNMR (400Mz, DMSO-d 6 ):δ7.36(s,82H),7.29(d,J=15.0Hz,170H),4.84(s,110H),4.74(s,55H),4.60(s,58H),3.18(s,30H) ,3.08(s,31H),2.80(d,J=13.8Hz,85H),1.94(t,J=3.5Hz,11H),1.93(s,53H),1.77(dd,J=65.0,60.0Hz, 211H), 1.56 (d, J=80.0Hz, 92H) ppm; 13 CNMR (100Mz, DMSO-d 6 ): δ167.96, 137.34, 128.64, 128.56, 127.89, 80.05, 64.91, 54.33, 50.62, 47.77, 31.93, 31.54, 15.74ppm; HRMS (...

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Abstract

The invention relates to application of an eight-membered oxygen-bridge heterocyclic compound as a pesticide synergist. Specifically, the invention discloses a compound with a structural formula as shown in (1) which is described in the specification. The compound can substantially reduce the LD50 or LC50 of pesticides under the condition of a low concentration and exerts strong synergistic effect on prevention and treatment of a plurality of pests like rice hoppers, whiteflies, cotton aphids, America periplaneta and houseflies.

Description

technical field [0001] The invention belongs to the field of pesticides. Specifically, the present invention relates to a new use of an eight-membered oxygen-bridged heterocyclic compound as a synergist for neonicotinoid insecticides. Background technique [0002] Most of the insecticides currently developed and utilized act on the nervous system of insects, such as ion channels, neurotransmitter receptors, and enzymes that play an important role in the nervous system. Nerve agents are the focus of research and development in recent years. Neonicotinoid insecticides represented by imidacloprid are the most deeply researched and most successfully developed and utilized insecticides acting on insect nAChRs. Their mechanism of action is to selectively act on nAChRs in the insect central nervous system, destroying The normal conduction of the central nervous system makes it in a state of extreme excitement and gradually paralyzes until death. It has the characteristics of high...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/90C07D498/18A01N51/00A01N47/40A01P7/04
CPCA01N43/90C07D498/14
Inventor 刘泽文李忠徐晓勇张懿熙邵旭升
Owner NANJING AGRICULTURAL UNIVERSITY
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