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Quinoline derivative and application thereof

A derivative, quinoline technology, applied in the field of quinoline derivatives, can solve the problems of rising insect species resistance, lower pest control rate, low insecticide control rate, etc., and achieves strong killing activity and environmental compatibility. High and efficient killing effect

Active Publication Date: 2015-05-27
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 agriculture and garden production, some insect species are difficult to control, and the resistance of some insect species has increased significantly. The control rate of existing insecticides on diseases and insect pests has been greatly reduced. A new type of agriculture and garden with excellent insecticidal activity has been developed. Insecticide is an inevitable measure to solve the current low rate of insecticide control

Method used

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  • Quinoline derivative and application thereof

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Experimental program
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Effect test

Embodiment 1

[0095] Intermediate Ⅰ: (R 6 =H) The specific synthetic steps are as follows:

[0096] Dissolve 1 mol of hydroquinone in 5L of ethanol, add 1 mol of potassium carbonate, reflux for 8 hours, distill off ethanol under reduced pressure at -0.095kPa, 80°C, then cool down to room temperature, add 1L of N,N-dimethylformamide , then add 1mol 2-chloro-5-trifluoromethylpyridine, heat up, react in the range of 50-55°C for 8h, then pour the reaction mixture into 5L water, stir, filter the precipitated crystals, and dry to obtain 200g intermediate Body Ⅰ, the yield was 78.4%.

[0097] Elemental analysis: C, 56.48; H, 3.16; F, 22.33; N, 5.49; O, 12.54.

[0098] m / z: 255.05 (100.0%), 256.05 (13.4%).

Embodiment 2

[0100] Synthesis of Intermediate II from Intermediate I: (R 4 = H, R 5 =CH 3 , R 6 =H) The specific synthetic steps are as follows:

[0101] Dissolve 0.05 mol of intermediate I in 100 ml of N,N-dimethylformamide, add 0.05 mol of potassium hydroxide powder and 0.05 mol of 3-methyl-4-chloronitrobenzene in sequence, heat up and reflux for 8 hours, and drop to After normal temperature, pour the reaction liquid into 1L water, extract with 100ml chloroform for 30min, divide chloroform, distill off chloroform at -0.095kPa, 100°C to obtain a viscous oily substance, use ethyl acetate / petroleum ether=8:2 chromatographic column After separation, 9.4 g of intermediate II was obtained with a yield of 44.3%.

[0102] Elemental analysis: C, 53.73; H, 2.85; Cl, ​​8.35; F, 13.42; N, 6.60; O, 15.07.

[0103] m / z: 424.04 (100.0%), 426.04 (32.1%), 425.05 (20.8%), 427.04 (6.8%), 426.05 (2.9%).

Embodiment 3

[0105] Synthesis of Intermediate III from Intermediate II: (R 4 =CH 3 , R 5 =CH 3 , R 6 =H) The specific synthetic steps are as follows:

[0106] Dissolve 0.05mol of intermediate II in 500ml of ethanol and place it in an autoclave with N 2 Replace 3 times, add 1g of 10% palladium carbon, pass H at 40-45°C 2 up to 22kg / cm 2 , until H 2 Until the pressure no longer drops, react for 8 hours, vent, filter out the filtrate, and distill under reduced pressure at -0.095kPa, 100°C to obtain an oily substance, which is separated by a chromatographic column with ethyl acetate / petroleum ether=8:2 to obtain 8.5g intermediate Body III, the yield was 45.5%.

[0107] Elemental Analysis: C, 64.17; H, 4.58; F, 15.22; N, 7.48; O, 8.55.

[0108] m / z: 374.12 (100.0%), 375.13 (21.9%), 376.13 (2.7%).

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Abstract

The present invention provides a quinoline derivative and an application thereof. The quinoline derivative has a structure shown in a general formula A. The quinoline derivative or an agriculture and garden acceptable acid addition salt thereof can be used as an active component of insecticides in the agriculture and the garden to kill insects of lepidoptera, homoptera, coleoptera and orthoptera, does not generate cross resistance, and also has stronger killing activity to pests which already have pesticide resistance.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to a quinoline derivative and its application. Background technique [0002] In modern agriculture and garden production, some insect species are difficult to control, and the resistance of some insect species has increased significantly. The control rate of existing insecticides on diseases and insect pests has been greatly reduced. A new type of agricultural and garden with excellent insecticidal activity has been developed. Insecticide is an inevitable measure to solve the current low rate of insecticide control. [0003] Quinoline is chemically active and can react with other substances. The resulting quinoline derivatives have broad-spectrum insecticidal activity and high biological activity. Contents of the invention [0004] The object of the present invention is to provide a kind of quinoline derivative and its application aiming at the problems existing in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12A01N47/06A01P7/04
CPCC07D401/12A01N47/06
Inventor 唐剑峰王如军吴雪潘光民刘杰李文宏
Owner SHANDONG UNITED PESTICIDE IND CO LTD
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