Nitrogen-containing bridged ring compound having insect disinfestation activity, preparation and uses thereof

A compound and unsaturated technology, applied in the field of nitrogen-containing bridged ring neonicotinoid insecticides, can solve the problems of narrow insecticidal spectrum and limited drug selectivity, and achieve expanded insecticidal spectrum, significant insecticidal activity, and The effect of broad spectrum

Active Publication Date: 2016-04-06
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, 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 it has become a constraint on this field. Neonicotinoid insecticides are mainly effective against Homoptera and Coleoptera pests, and their relatively narrow insecticidal spectrum also limits the selectivity of insecticides in pest control

Method used

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  • Nitrogen-containing bridged ring compound having insect disinfestation activity, preparation and uses thereof
  • Nitrogen-containing bridged ring compound having insect disinfestation activity, preparation and uses thereof
  • Nitrogen-containing bridged ring compound having insect disinfestation activity, preparation and uses thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0109] The preparation method of the compound of the present invention

[0110] The compound of general formula A and B structure of the present invention can be prepared by the following method, but the conditions of the method, such as the amount of reactant, solvent, base, compound used, reaction temperature, reaction time required etc. are not limited to the following explanations. The compound of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in the specification or known in the art. Such a combination can be easily performed by those skilled in the art to which the present invention belongs.

[0111] Protonic acids or Lewis acids used in the reaction include (but are not limited to): hydrochloric acid, acetic acid, sodium dihydrogen phosphate, p-toluenesulfonic acid, trifluoroacetic acid, boron trifluoride, aluminum trichloride, ferric chloride, magnesium chloride , cobalt chloride, strontium chloride...

Embodiment 1-32

[0133] Example 1-32: Preparation of heterobridged ring neonicotinoid compounds

Embodiment 1

[0134] Example 1: 1-((6-chlorophen-3-yl)methyl)-9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-cycloimine Synthesis of imidazo[1,2-a]azepane:

[0135]

[0136] 1.270g (5.0mmol) of 2-chloro-5-((2-(nitromethylene) imidazolin-1-yl) methyl) benzene and 0.266g (5.0mmol) of ammonium chloride were added to 20ml Acetonitrile, slowly dropwise add 0.430g (5.0mmol) of succinic dialdehyde. After reacting for 24 hours, the solvent was removed, and the pure product was obtained as light yellow powder through column chromatography separation, with a yield of 38%. 1 HNMR (400MHz, DMSO-d 6 )δ8.66(d,J=2.9Hz,1H),8.01(dd,J 1 =8.0Hz,J 2 =2.0Hz,1H),7.30(d,J=14.9Hz,1H),4.81(s,2H),4.28(t,J=7.3Hz,1H),3.96(t,J=8.7Hz,1H), 3.18(t, J=13.9Hz, 1H), 3.05(t, J=13.8Hz, 1H), 2.89(t, J=13.7Hz, 1H), 2.69(t, J=13.9Hz, 1H), 2.27( s,1H),1.95–1.75(m,1H),1.72–1.41(m,2H),1.32–1.11(m,1H)ppm; 13 CNMR (100MHz, DMSO-d 6 ): δ149.48, 148.61, 138.84, 130.35, 123.76, 64.35, 54.68, 50.62, 49.31, 29.97, 27.81ppm; HRMS(ES+)C 14...

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Abstract

The present invention relates to a nitrogen-containing bridged ring compound having insect disinfestation activity, preparation and uses thereof, and particularly provides a compound having a structure represented by a general formula I, a preparation method and uses thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, R, n and Z are defined in the specification. The present invention further relates to an agricultural composition containing the compound or a pesticide acceptable salt, and uses of the agricultural composition. According to the present invention, the compound provides high insect disinfestation activity on Homoptera pests, Lepidoptera pests and other agricultural and forestry pests such as aphid, planthopper, whiteflies, leafhoppers, thrips, Helicoverpa armigera Hubner, Pieris rapae, diamondback moth, Spodoptera litura, armyworms and the like. The general formula I is defined in the specification.

Description

technical field [0001] The invention relates to a nitrogen-containing bridged ring neonicotinoid insecticide, a preparation method and application thereof. technical background [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 system properties, appropriate field stability and environmental friendliness have become an important hotspot for the creation of new pesticides. Later, a series of neonicotinoid insecticides such as thiacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram, and dinotefuran were successively developed. Due to their high insecticidal activity, broad insecticidal spectrum, low toxicity to mammals and aquatic animals, good system properties and appropriate field stability, neonicotinoid insecticides have become an important hotspot for pesticide development...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/18C07D471/18C07D513/18A01N43/90A01P7/04A01P5/00
Inventor 李忠徐晓勇徐仁博钱旭红邵旭升须志平程家高宋恭华
Owner EAST CHINA UNIV OF SCI & TECH
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