Fluoropyridine-containing piperazine amide compounds and application thereof

A technology for pyridine piperazine amide and compound is applied in the field of fluorine-containing pyridine piperazine amide compounds, and achieves the effects of good biodegradability, low production cost and simple synthesis process

Active Publication Date: 2018-11-16
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, the compound of general formula I as shown in the present invention and its use as agricultural and forestry acaricides have not been reported

Method used

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  • Fluoropyridine-containing piperazine amide compounds and application thereof
  • Fluoropyridine-containing piperazine amide compounds and application thereof
  • Fluoropyridine-containing piperazine amide compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0024] Example 1, the preparation of intermediate III

[0025]

[0026] Add 17.2g (0.2mol) of anhydrous piperazine and 60mL of methanol into a 250mL reaction flask, stir to dissolve and raise the temperature to 40°C, then dilute 21.6g (0.1mol) of 2,3-dichloro-5-(tri Fluoromethyl)pyridine, slowly added dropwise, after the drop, reacted at a constant temperature of 40°C for 6h, tracked by TLC until the reaction of the raw materials was complete, lowered to room temperature, filtered with suction, and the filtrate was rotary evaporated in vacuo to remove methanol, and a white solid was precipitated. Add water and stir to dissolve the remaining free Water piperazine, filtered with suction, and washed the filter cake with water to obtain 22.6 g of a white solid with a melting point of 65.8-67.3°C and a yield of 85%.

[0027] 1 H NMR (500MHz, DMSO-d6), δ (ppm) 8.53 (s, 1H), 8.15 (s, 1H), 3.37–3.35 (t, 4H), 2.82–2.80 (t, 4H).

example 2

[0028] Example 2, compound I 1 preparation of

[0029]

[0030] Take 5.3g (0.02mol) of intermediate III and add it to a 250mL reaction flask, then add 35mL of ethyl acetate, then add 2.22g of triethylamine, add 10mL of ethyl acetate and 3.45g (0.02mol) of 3-ethylamine dropwise under stirring - Mixture of 1-methyl-1H-pyrazole-5-carbonyl chloride, react at room temperature for 30 minutes after dropping, TLC traces the complete reaction of intermediate III, add 100mL of water and stir, then separate the liquids, and dry the organic phase with anhydrous sodium sulfate , ethyl acetate was removed by rotary evaporation, and 7.3 g of white solid was obtained by cooling, with a melting point of 103.0-105.1° C. and a yield of 91%.

[0031] 1 H NMR (500MHz, DMSO-d6) δ (ppm) 8.56 (s, 1H), 8.23 ​​(s, 1H), 6.38 (s, 1H), 3.97 (s, 2H), 3.82 (s, 3H), 3.58– 3.44(m,6H),2.57–2.51(m,2H),1.24–1.21(t,3H).

[0032] According to example 2 in I 1 Synthetic method for synthesizing other compoun...

example 3

[0046] Example 3, acaricidal activity assay

[0047] The acaricidal egg activity was determined by dipping method and statistical correction of pest mortality. The specific process is as follows: dilute the test agent to the required concentration according to the active ingredients, draw 50mL of the liquid medicine under aseptic conditions and inject it into the petri dish, and then respectively immerse the cinnabar mite eggs (mite eggs normally raised according to the indoor standardized method) population), and a plate with 50 mL of sterilized water added was used as a blank control. Place the Petri dish in a constant temperature incubator at 24±1°C. After 48 hours, the mortality rate was investigated and counted.

[0048] The acaricidal activity test result of table 1 series compound

[0049]

[0050] According to the test results, the compound of the present invention has excellent acaricidal activity, and at the same dose, the compound of the present invention I 1...

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PUM

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Abstract

The invention provides fluoropyridine-containing piperazine amide compounds. The structure of the compounds is represented as the general formula I shown in the description, wherein R in the formula is as follows: C1-C5 alkyl, C1-C4 alkoxy, substituted phenyl and heterocyclic aryl. The compounds shown as the formula I have inhibiting and killing effects on harmful mites and mite eggs, and can be taken as miticides to be applied to control of agricultural and forestry mite damage.

Description

technical field [0001] The invention belongs to the field of acaricides in pesticides, and in particular relates to a fluorine-containing pyridine piperazine amide compound and an application thereof. Background technique [0002] Mites destroy the normal physiological functions of plants, resulting in reduced yield and normal growth of crops. There are many acaricides to prevent mite damage, such as bromofen, abamectin, spirodiclofen, and pyraclofen. Spirodiclofen has a good killing effect on mites, but with the extensive use of pesticides, the resistance of mites to pesticides has increased. 2,3-Dichloro-5-(trifluoromethyl)pyridine is a fluorine-containing organic intermediate with high activity and low toxicity. It is also a key intermediate for many high-efficiency insecticides, acaricides, and fungicides. For example, Acetamizuron, Fluazinam and Fluopyram. Piperazine itself has excellent biological activity and is widely used in pesticides. In the prior art, there is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C07D409/12C07D213/74A01N43/60A01P7/02
CPCA01N43/60C07D213/74C07D401/12C07D409/12
Inventor 王明慧彭壮崔焕奇崔建强许良忠
Owner QINGDAO UNIV OF SCI & TECH
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