Nicotinamide compound as well as preparation method and application thereof

A compound, the technology of nicotinamide, applied in the field of nicotinamide compound and its preparation, can solve the problems of environmental pollution, plant drug resistance, irrational use of chemical pesticides, etc., and achieve a wide range of effects

Inactive Publication Date: 2017-11-24
河北蓝泰化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the long-term irrational use of chemical pesticides has also brought many disadvantages such as environmental pollution, direct poisoning to non-target organisms, and negative effects such as plant resistance.

Method used

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  • Nicotinamide compound as well as preparation method and application thereof
  • Nicotinamide compound as well as preparation method and application thereof
  • Nicotinamide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0027] The preparation method of the route one comprises the following steps:

[0028] A, potassium hydroxide is added in the flask under stirring state, then slowly add methanol solution, form potassium hydroxide methanol solution after stirring and cooling, stand for use;

[0029] B. Add cyanoacetamide to the four-neck flask under stirring, then add methanol solution, stir and heat to reflux, the reaction solution turns from turbid to transparent, and then add the raw material ethyl trifluoroacetoacetate, in which cyanoacetamide and trifluoroacetoacetate The molar ratio of ethyl ester is 1:0.5~1.5, add potassium hydroxide methanol solution while maintaining the reflux state, continue to reflux for 24 hours, and wait for the complete reaction of cyanoacetamide to obtain the reflux solution;

[0030] C. Distill the reflux solution, recover 3 / 4 methanol, add cold water to the residue, under cooling condition, use dilute hydrochloric acid to adjust PH=3-4, after stirring for 0.5...

Embodiment 1

[0043] Example 1: Preparation of 2,6-dichloro-4-(trifluoromethyl)nicotinamide

[0044] (1) Preparation of intermediate 2,6-dihydroxy-3-cyano-4-(trifluoromethyl)pyridine

[0045] Take 29.8g (0.53mol) of potassium hydroxide and put it into a 250mL four-necked bottle equipped with mechanical stirring and reflux condenser, slowly add 100mL of methanol, stir and cool for later use; put 43.4g (0.52mol) of cyanoacetamide into a bottle equipped with mechanical stirring , constant pressure dropping funnel, drying tube and 500mL four-necked flask of reflux condenser, add 150mL of methanol, mechanically stir and heat to reflux, after the reaction solution changes from turbid to light yellow and transparent, add 100g (0.54mol) trifluoroacetoacetic acid Ethyl ester, keep the reflux state, slowly add the prepared potassium hydroxide methanol solution dropwise, heat and reflux for 24 hours, the reaction of the central control raw material cyanoacetamide is complete, change the reflux device ...

Embodiment 2

[0050] Example 2: Preparation of 2,6-difluoro-4-(trifluoromethyl)nicotinamide

[0051] (1) Preparation of intermediate 3-cyano-2,6-difluoro-4-(trifluoromethyl)pyridine

[0052] Add 53 grams of 2,6-dichloro-3-cyano-4-(trifluoromethyl)pyridine, 35 grams of KF, 10 grams of 18 crown ether, and 250 ml of DMF into a 250ml four-necked bottle, heat up to 130 degrees, and keep warm for 3 -5 hours, after the reaction is completed, add water to precipitate a yellow solid, 30 g after drying, hplc92%, yield 65.5%.

[0053] (2) Preparation of 2,6-difluoro-4-(trifluoromethyl)nicotinamide

[0054] Add 25 grams (120 mmol) of 3-cyano-2,6-difluoro-4-(trifluoromethyl)pyridine and 75 grams of 98% concentrated sulfuric acid into a 250ml four-necked bottle, heat up to 90-95 degrees, and keep warm for 3 hours After the temperature was lowered, it was added into water, and a pale yellow solid was precipitated. After drying, 23 g was obtained, hplc93%, and the yield was 85%.

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Abstract

The invention provides a nicotinamide compound of which the structural formula is as shown in the specification, in the formula, R1 and R2 are one of F, Cl, Br, I, methyl, tertiary butyl, trifluoromethyl, halogenated alkyl, hydroxyl, nitryl, amino, cyan, alkynyl, amidine, diazanyl, sulfonyl, sulfydryl, hydrazide or acylamino, 2-furan and 2-thiophene; R1 and R2 are identical or different; and R3 in the formula is one of hydrogen, sulfydryl and amino. Compared with other widely used amide compounds with a good pesticide effect, the nicotinamide compound is relatively good in activity. The nicotinamide compound provided by the invention has no interaction resistance with other pesticides, takes multiple functions into play, and thus is relatively wide in application.

Description

technical field [0001] The invention belongs to the technical field of chemistry and chemical engineering, and relates to the preparation of pesticides, in particular to a nicotinamide compound and its preparation method and application. Background technique [0002] my country is a large agricultural country, with an area of ​​about 400 million hectares of crops. However, due to the occurrence of crop diseases, insect pests and weeds all year round, about 800,000 tons of pesticides need to be produced and used every year, and pesticides have become an indispensable factor of production in agricultural production. However, the long-term irrational use of chemical pesticides has also brought many disadvantages such as environmental pollution, direct toxicity to non-target organisms, and negative effects such as plant resistance. Therefore, research on new pesticides with good environmental compatibility, safety, low residue and economy will become the development trend in th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82A01N43/40A01P7/04
Inventor 郭明孟水强田鹏会侯建军
Owner 河北蓝泰化工科技有限公司
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