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Nitrogen (sulfur) containing bridge ring compound with insecticidal activity, preparation method and application

A compound and carbonyl technology, applied in the field of nitrogen-containing bridged ring neonicotinoid insecticides, can solve the problems of limited drug selectivity and narrow insecticidal spectrum, achieve significant insecticidal activity, expand insecticidal spectrum, and improve insecticidal activity. The effect of insect activity

Inactive Publication Date: 2013-08-14
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 (sulfur) containing bridge ring compound with insecticidal activity, preparation method and application
  • Nitrogen (sulfur) containing bridge ring compound with insecticidal activity, preparation method and application
  • Nitrogen (sulfur) containing bridge ring compound with insecticidal activity, preparation method and application

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preparation example Construction

[0106] The preparation method of the compound of the present invention

[0107] The compound represented by the general formula 1 of the present invention can be prepared by the following method, but the conditions of the method, such as reactants, solvents, bases, the amount of the 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.

[0108] The acid used in the reaction is protonic acid or Lewis acid, including (but not limited to): hydrochloric acid, acetic acid, sodium dihydrogen phosphate, p-toluenesulfonic acid, trifluoroacetic acid, boron trifluoride, aluminum trichloride, trichloro Iron chloride, magnesium chloride, cobalt chlo...

Embodiment 1-44

[0141] Example 1-44: Preparation of heterobridged ring neonicotinoid compounds

Embodiment 1

[0142] Example 1 1-((6-chloropyridin-3-yl)methyl)-8-nitro-1,2,3,5,6,7-hexahydro-5,7-cycloimidoimidazo[ 1,2-a] the synthesis of pyridine (compound A-1):

[0143]

[0144] 1.270g (5.0mmol) of 2-chloro-5-((2-(nitromethylene) imidazolin-1-yl) methyl) pyridine and 0.531g (10.0mmol) of ammonium chloride were added to 20ml Acetonitrile, slowly drop 0.360g (5.0mmol) of malondialdehyde. 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 42%. 1 H NMR (400MHz, DMSO-d 6 )δ8.71(d, J=2.9Hz, 1H), 8.05(dd, J 1 =8.0Hz,J 2 =2.0Hz, 1H), 7.34(d, J=8.0Hz, 1H), 4.84(s, 2H), 4.00(t, J=7.6Hz, 1H), 3.90(t, J=9.5Hz, 1H), 3.04(m, 4H), 2.41(m, 1H), 1.84(m, 1H)ppm; 13 C NMR (100MHz, DMSO-d 6 ): δ150.02, 149.48, 148.61, 138.84, 130.35, 123.76, 54.68, 50.86, 50.62, 37.44ppm; HRMS(ES+)C 13 h 14 35 ClN 5 o 2 (M+H) + , calculated value: 308.0836; measured value: 308.0756; C 13 ...

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Abstract

The invention relates to a nitrogen (sulfur) containing bridge ring compound with insecticidal activity, a preparation method and an application. Specifically, the invention discloses a compound with a general formula I or an optical isomer, a cis-trans-isomer or an agricultural pharmacology acceptable salt of the compound, and a preparation method thereof, wherein R1, R2, R3, R4, R5, R6, R, m, X and Z are respectively as defined in the specification. The invention also discloses an agricultural composition comprising the above compound and an application thereof. The above compound has high insecticidal activity for homoptera and lepidoptera agriculture and forestry insects, such as aphids, plant hoppers, whiteflies, cotton bollworms, prodenia litura, armyworm, etc. The general formula 1 is shown in the specification.

Description

technical field [0001] The invention relates to a nitrogen (sulfur) 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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IPC IPC(8): C07D487/18C07D487/08C07D495/18C07D513/18A01N43/90A01P7/04
Inventor 李忠徐晓勇徐仁博钱旭红邵旭升须志平曾步兵宋恭华
Owner EAST CHINA UNIV OF SCI & TECH
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