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Compound N-fluorobenzamido-N'-phenylthiocarbamide as well as preparation and application thereof

A technology of fluorobenzylamino and fluorobenzylhydrazide, which is applied in the fields of botanical equipment and methods, applications, organic chemistry, etc., can solve problems such as the reduction of arable land area, and achieve energy saving and mild reaction conditions. , the effect of convenient operation

Inactive Publication Date: 2012-11-21
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, while the demand for food has increased, the area of ​​arable land has continued to decline

Method used

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  • Compound N-fluorobenzamido-N'-phenylthiocarbamide as well as preparation and application thereof
  • Compound N-fluorobenzamido-N'-phenylthiocarbamide as well as preparation and application thereof
  • Compound N-fluorobenzamido-N'-phenylthiocarbamide as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1, the synthesis of compound N-o-fluorobenzamido-N'-phenylthiourea 2a

[0037] (1) Synthesis of intermediate o-fluorobenzoic hydrazide 1a

[0038] Get 4.2g (30mmol) of 2-fluorobenzoic acid and 50ml of anhydrous methanol, add to a 100ml beaker and mix, then add 3ml of concentrated sulfuric acid (concentration is 98%), and heat to reflux at 70°C to 100°C for 7 ~8h, cooling, with anhydrous Na 2 CO 3 Adjust to neutral (pH=7~8), filter with suction, add 3g (43mmol) of NH 2 NH 2 ·H 2 O (mass concentration 85%), heated to 70 ° C ~ 100 ° C, refluxed 7 ~ 8h, to obtain the intermediate o-fluorobenzoic hydrazide 1a.

[0039] (2) Add 0.4g (2.7mmol) of 2-fluorobenzoic hydrazide and 0.4g (3.0mmol) of phenyl isothiocyanate in an agate mortar, grind intermittently for 3-5 hours, and the reactants are viscous The thick liquid turned into a white solid, and the target product was obtained. Recrystallized from absolute ethanol to obtain pure N-fluorobenzamido-N'-phenylth...

Embodiment 2

[0041] Embodiment 2, the synthesis of compound N-p-fluorobenzamido-N'-phenylthiourea 2b

[0042] (1) Synthesis of intermediate p-fluorobenzoic hydrazide

[0043] Get 4.2g (30mmol) of p-fluorobenzoic acid and 50ml of anhydrous methanol, add them to a 100ml beaker and mix them, then add 3ml of concentrated sulfuric acid (concentration is 98%), and heat to reflux at 70°C to 100°C for 7~ 8h, cooling, with anhydrous Na 2 CO 3 Adjust pH=7~8, filter with suction, add 3g (43mmol) NH to the filtrate 2 NH2 ·H 2 O (mass concentration 85%), heated to 70 ° C ~ 100 ° C, refluxed 7 ~ 8h, to obtain the intermediate fluorobenzoic hydrazide 1b.

[0044] (2) Add 0.4g (2.7mmol) p-fluorobenzoic hydrazide and 0.4g (3.0mmol) phenyl isothiocyanate to an agate mortar, grind intermittently for 3-5 hours, and the reactant is formed from viscous liquid Turn into a white solid, that is, the target product. Recrystallized from absolute ethanol to obtain pure N-p-fluorobenzamido-N'-phenylthiourea 2b. ...

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Abstract

The invention provides a compound N-fluorobenzamido-N'-phenylthiocarbamide, which is prepared by the following steps of: mixing fluorobenzoic acid with absolute methanol, then adding concentrated sulfuric acid, controlling the temperature at 70-100 DEG C for refluxing for 7-8 hours; cooling, regulating pH with anhydrous sodium carbonate to equaling 7-8, extracting and filtering; adding amount of NH2NH2.H2O in the filtrate to continue reflux for 7-8 hours to thereby obtain an intermediate of fluorobenzoyl hydrazine; adding the fluorobenzoyl hydrazine and phenylthiocarbonimide in a certain proportion into an agate mortar for being ground intermittently for 3-5 hours, obtaining a target product until the reactant is changed from viscous liquid into white solid; recrystallizing the product with absolute alcohol to obtain pure N-fluorobenzamido-N'-phenylthiocarbamide. A result from experiments of biological activity shows that: the compound N-fluorobenzamido-N'-phenylthiocarbamide is excellently facilitative for the growth of wheat seedling root.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and relates to a compound N-fluorobenzamido-N'-phenylthiourea and a preparation method thereof; the invention also relates to a compound N-fluorobenzamido-N'-benzene The use of thiourea as a plant growth regulator. Background technique [0002] With the development of the economy and the improvement of people's living standards, the human demand for food crops is increasing day by day. However, while the demand for food has increased, the area of ​​arable land has continued to decline. Therefore, increasing the grain output per unit area is the main way to solve this contradiction. Plant growth regulators play an important role in efforts to increase food production. [0003] Amidothiourea compounds have various biological activities such as herbicide, insecticide, antivirus, and regulation of plant growth. In addition, fluorine-containing compounds also have unique biological activ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C337/06A01N47/34A01P21/00
Inventor 张有明王雅琳林奇魏太保
Owner NORTHWEST NORMAL UNIVERSITY