Nicotine compound containing double benzene and preparation method and use thereof

An aniline compound and compound technology, applied in the field of bisphenyl-containing nicotinic compounds and their preparation, can solve the problems of reduced pest killing rate and pest resistance, and achieve strong killing activity, high-efficiency killing, Broad-spectrum insecticidal effect

Active Publication Date: 2013-07-17
SHANDONG UNITED PESTICIDE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In modern agricultural production, the excessive use of pesticides to ensure the production of crops has resulted in the resistance of pests, and the killing rate of existing pesticides on pests has been greatly reduced

Method used

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  • Nicotine compound containing double benzene and preparation method and use thereof
  • Nicotine compound containing double benzene and preparation method and use thereof
  • Nicotine compound containing double benzene and preparation method and use thereof

Examples

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preparation example Construction

[0062] A preparation method of a bisphenyl-containing nicotinic compound of the present invention comprises the following steps:

[0063] ① Add the aniline compound with the general structural formula A and the halide benzyl compound with the general structural formula B into the solvent in a molar ratio of 1-2:1, then add the acid-binding agent, and stir at 20-150°C React for 6-12h, filter to remove the solid, wash with hydrochloric acid to remove the remaining aniline compound A in the filtrate, and the remaining liquid is obtained by column chromatography to obtain intermediate II,

[0064] ;

[0065]②The intermediate II obtained in step ① and 2-chloro-5-chloromethylpyridine or 2-chloro-5-chloromethylthiazole are sequentially added to the solvent in a molar ratio of 1:1, and the bound The acid agent is added to the reaction solution in batches within 5-8 hours. After the addition, the reaction solution is poured into water, and the solid is precipitated. The solid is obt...

Embodiment 1

[0096] Example 1, the specific preparation steps of bisphenyl-containing nicotinic compound (1) are as follows:

[0097] ① Add 0.1mol 2,6-difluoroaniline and 0.1mol benzyl chloride to 300ml methanol in turn, add 40g (0.1mol) sodium hydroxide, stir and react at 20°C for 12h, filter to remove solids, and wash the filtrate with hydrochloric acid Wash to remove the remaining 2,6-difluoroaniline, and the remaining liquid is obtained by column chromatography of ethyl acetate:petroleum ether=6:4 to obtain intermediate II;

[0098] ② Add the intermediate II obtained in step ① and 0.1mol 2-chloro-5-chloromethylpyridine to 300ml methanol in sequence, and add 40g (0.1mol) sodium hydroxide to the reaction solution in 4 batches within 8 hours at 30°C After the addition, the reaction solution was poured into 1000ml of water, the solid was precipitated, and the solid was obtained by filtration, and 29.25g of white solid was obtained by column chromatography of ethyl acetate:petroleum ether=9...

Embodiment 2

[0099] Example 2, the specific preparation steps of the bisphenyl-containing nicotinic compound (11) are as follows:

[0100] ① Add 0.2mol 2,6-dichloroaniline and 0.1mol p-fluorobenzyl bromide to 1500ml propanol in turn, add 138.19g (1mol) potassium carbonate, stir and react at 150°C for 6h, filter to remove the solid, and use the filtrate Wash with hydrochloric acid to remove the remaining 2,6-dichloroaniline, and the remaining solution is subjected to column chromatography of ethyl acetate:petroleum ether=7:3 to obtain intermediate II;

[0101] ② Add the intermediate II obtained in step ① and 0.1mol 2-chloro-5-chloromethylpyridine to 1500ml propanol in sequence, and add 138.19g (1mol) potassium carbonate to the reaction solution in 4 batches within 5h at 100°C After the addition, the reaction solution was poured into 1000ml of water, the solid was precipitated, and the solid was obtained by filtration, and 34.28g of white solid was obtained by column chromatography of ethyl ...

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Abstract

The invention provides a nicotine compound containing double benzene and a preparation method and use thereof. The nicotine compound containing double benzene has the structural formula shown in the specification. The invention discloses a formula of the nicotine compound containing double benzene, the preparation method and use for insecticide. The compound can be used for killing larva and adult in lepidoptera, homoptera, coleoptera and orthoptera.

Description

technical field [0001] The invention belongs to the technical field of insecticides, and in particular relates to a bisphenyl-containing nicotinic compound and a preparation method and application thereof. Background technique [0002] In modern agricultural production, the excessive use of pesticides to ensure the production of crops has resulted in the resistance of pests, and the killing rate of existing pesticides on pests has been greatly reduced. In 2012, the National Agricultural Technology Extension Service Center monitored the pesticide resistance of major crop diseases and insect pests at 76 drug resistance monitoring points in 16 provinces including Hebei and Shanxi. The level of insecticide resistance has increased significantly, and the number of resistant populations has increased year by year. Some pests have high resistance to imidacloprid, acetamiprid and other insecticides. [0003] Therefore, developing a new type of insecticide with high insecticidal act...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61C07D277/32A01N43/78A01N43/40A01P7/04
Inventor 唐剑峰潘光明刘杰张晓霞牛纪胜
Owner SHANDONG UNITED PESTICIDE IND CO LTD
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