Nitrogenous heterocyclic compounds with insecticidal activity, preparation and uses thereof

一种化合物、六元杂环的技术，应用在新型杀虫剂领域，能够解决限制用药选择性、窄杀虫谱等问题

Inactive Publication Date: 2009-07-29
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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  • Nitrogenous heterocyclic compounds with insecticidal activity, preparation and uses thereof
  • Nitrogenous heterocyclic compounds with insecticidal activity, preparation and uses thereof
  • Nitrogenous heterocyclic compounds with insecticidal activity, preparation and uses thereof

Examples

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preparation example Construction

[0076] The preparation method of the compound of the present invention

[0077] The compounds of the present invention can be synthesized by the reaction steps described above. Those skilled in the art can synthesize the compound of formula (a) in the reaction step according to the prior art literature, for example, refer to WO2006056108A1 and WO2007101369A1.

[0078] In the specific embodiment of the present invention, the synthetic method of formula (I) compound is as follows:

[0079]

[0080]

[0081] In other specific embodiments of the present invention, the synthetic method of formula (II) compound is as follows:

[0082]

[0083] In other specific embodiments of the present invention, the synthetic method of formula (III) compound is as follows:

[0084]

[0085] In a specific embodiment, compounds of formula (I) can be prepared by the following reactions:

[0086] (1) Add the acetonitrile solution of 2-chloro-5-chloromethylpyridine dropwise into the dia...

Embodiment 1

[0114] Example 1.2-chloro-5-((2-(2-(furan-2-yl)-1-nitrovinyl)-4,5-dihydroimidazolidin-1-yl)methyl)pyridine (compound 1) Synthesis of

[0115] Using 0.03mol of 2-chloro-5-chloromethylpyridine as a starting material, prepare 2-chloro-5-(2-nitromethylene-imidazolidin-1-ylmethanol according to the method described in WO2006056108A1 and WO2007101369A1 Base)-pyridine, the yield was 56%; Rf = 0.46 (petroleum ether: ethyl acetate = 1: 1); mp = 156.9 ° C ~ 161.8 ° C. GC MS (m / s) 220(25), 126(100), 90(9).

[0116] Synthesis of 2-chloro-5-((2-(2-(furan-2-yl)-1-nitrovinyl)-4,5-dihydroimidazol-1-yl)methyl)pyridine

[0117]

[0118] 1.27g (0.005mol) of 2-chloro-5-(2-nitromethylene-imidazolidin-1-ylmethyl)-pyridine, 30ml of anhydrous acetonitrile, 0.576g (0.006mol) of furfural, A catalytic amount of HCl was placed in a 50 ml round bottom flask. After stirring at room temperature, a large amount of solids precipitated after about 2 hours, the reaction was stopped, and the crude produ...

Embodiment 2

[0120] Example 2.2-chloro-5-((2-(2-(furan-3-yl)-1-nitrovinyl)-4,5-dihydroimidazolidin-1-yl)methyl)pyridine (compound 2) Synthesis of

[0121]

[0122] 1.27g (0.005mol) of 2-chloro-5-(2-nitromethylene-imidazolidin-1-ylmethyl)-pyridine, 30ml of anhydrous acetonitrile, 0.576g (0.006mol) of furan- 3-Formaldehyde, a catalytic amount of HCl was placed in a 50 ml round bottom flask. After stirring at room temperature, a large amount of solids precipitated after about 2 hours, the reaction was stopped, and the crude product was obtained by filtration. The pure product obtained by recrystallization was 0.862 g of taupe powder solid, and the yield was about 51.9%.

[0123] mp=175.3-175.9°C; 1 H NMR (400Mz, DMSO-d 6 ): δ8.86(s, 1H), 8.70(s, 1H), 8.27(d, J=2.4Hz, 1H), 8.02(s, 1H), 7.71(dd, J 1 =2.4Hz,J 2 =8.4Hz, 1H), 7.52(d, J=8.4Hz, 1H), 6.61(d, J=0.8Hz, 1H), 4.75(d, J=15.2Hz, 1H), 4.68(d, J=15.2 Hz, 1H), 4.05-4.25 (m, 4H) ppm; 13 C NMR (100Mz, DMSO-d 6 ): δ157.9, 154.9, 150....

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Abstract

The invention relates to a compound which is provided with formula (A) and contains N heterocycles or open loops, wherein, R1, R2, R3, R4, R5, Y, Z and W are respectively defined as in the specification. A preparation method of a new insecticide and the usage thereof are also disclosed by the invention. The compound and derivatives thereof have high insecticidal activity on agricultural and forestry pests of homoptera, Lepidoptera, and the like and aphids, plant hoppers, whiteflies, leafhoppers, thrips, cotton bollworms, cabbage caterpillars, diamondback moths, cotton leafworms, armyworms, etc.

Description

technical field [0001] The invention relates to a novel neonicotinoid-like insecticide, its preparation method and application. technical background [0002] In the mid-1980s, Bayer developed the first neonicotinoid insecticide, imidacloprid, and became one of the most successful new insecticides. The neonicotinoid insecticide represented by imidacloprid has high insecticidal activity. It has a wide insecticidal spectrum, low toxicity to mammals and aquatic animals, and has good system properties, appropriate field stability and environmental friendliness, and has become an important hot spot for the creation of new pesticides. Later, a series of neonicotinoid insecticides such as thiacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram, and dinotefuran were developed successively (European patents 247477, 296453, 685477, 235725, 235725 , 315826, 192060, 244777, 0386565, 580553, and 1031566, Japanese patents 62292765, 8259568, 8291171, and 7242633). [0003] Howeve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D409/14C07D401/12C07D413/12C07D417/14A01N43/50A01N43/54A01P7/00
CPCC07D401/12A01N43/50C07D417/14A01N43/08C07D405/14A01N43/78A01N43/42C07D409/12A01N43/54C07D417/12A01N43/76A01N43/40C07D405/06C07D409/14A01N43/34A01N37/52
Inventor 李忠钱旭红邵旭升徐晓勇陶黎明宋恭华黄青春
Owner EAST CHINA UNIV OF SCI & TECH
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