CN1059208C - Preparation method of heteroatamic substituted phenyl urea - Google Patents
Preparation method of heteroatamic substituted phenyl urea Download PDFInfo
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- CN1059208C CN1059208C CN98112848A CN98112848A CN1059208C CN 1059208 C CN1059208 C CN 1059208C CN 98112848 A CN98112848 A CN 98112848A CN 98112848 A CN98112848 A CN 98112848A CN 1059208 C CN1059208 C CN 1059208C
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- preparation
- tdz
- heteroatamic
- substituted phenyl
- urea
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- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention relates to a preparation method of heteroatamic substituted phenyl urea, which is a method for synthesizing N-phenyl-N'-1.2.3-thiadiazole-5-urea from phenyl isocyanate and 5-amido-1.2.3-thiadiazole. The abbreviation of the product is TDZ. The present invention is characterized in that standing reaction is completed in a water bath at 8 to 16 DEG C. The preparation method has the advantages of high yield, simplicity, convenience and easy operation. The TDZ as a plant growth regulator can be widely applied to agricultural production.
Description
The invention belongs to heteroatamic substituted phenyl urea preparation method's improvement, relate to the technical field of crop growth regulator.
The alleged heteroatamic substituted phenyl urea of the present invention is N-phenyl-N '-1,2,3-thiadiazoles-5-urea, and English name Thidiazuron is called for short TDZ, is faint yellow mealy crystal, 217 ℃ of fusing points (decomposition).TDZ uses and grows up as the defoliant that grows cotton, and when finding TDZ when adding lower concentration in the substratum in nineteen eighty-two, can obviously promote the Sieve Bean callus Growth, has than the stronger effect of zeatin (ZT); Then in soybean callus tissue, Radix Dauci Sativae cotyledon and tobacco plant regeneration, test respectively, confirmed the highly active cytokinin effect of TDZ; Other tests have confirmed that also TDZ has the effect of evoked callus, promotion differentiation, and this tissue culture to plant has produced very big influence.Along with going deep into to the TDZ applied research, its quality to apple, bear fruit, bloom and the fruit shape influence more be subjected to people's attention, particularly can make the apple fruit shape index improve more than 10%, the high quality fruit rate is enhanced about more than once, volume increase reaches 15-30%, the effect that increases apple hardness and fruit face smooth finish is arranged simultaneously, improved the commodity rate of fruit greatly.
TDZ is synthesized in 1976 by people such as Arndt, (Arndt E.R.et al., 1976 ,-plant pbysiol.57:98-99).Its concrete synthetic method is: 5-amido-1,2,3-thiadiazoles and phenylcarbimide are in tetrahydrofuran solvent, and standing and reacting is 24 hours under room temperature, obtain the TDZ product except that after desolvating, and its yield is up to 76%.This method is continued to use for many years always, and not seeing has improved report.
The objective of the invention is to, improve the preparation method of TDZ, improve the product yield, and make it to have that method is simple, processing ease, the advantage that reduces production costs.
The alleged N-phenyl-N '-1,2 of the present invention, the preparation method of 3-thiadiazoles-5-urea is: 5-amido-1,2,3-thiadiazoles and phenylcarbimide are catalyzer with the triethylamine in tetrahydrofuran solvent, standing and reacting 24 hours is removed and is desolvated, and obtains product; It is characterized in that described standing and reacting is to finish in 8-16 ℃ water-bath.
By preparation method of the present invention, the yield of TDZ is reached more than 86%, the highlyest surpass 90%, thereby because the raising of yield reduces production cost, and have that method is simple, the advantage of processing ease, make TDZ step and go a step further to the application of agriculture production.
Describe technical solution of the present invention in detail below in conjunction with embodiment.
Example 1. is got the 5-amido-1,2 of 10.1 grams, and the 3-thiadiazoles is dissolved in the tetrahydrofuran solvent of 80ml, removes by filter impurity; The phenylcarbimide that in filtrate, adds 12ml, the triethylamine that adds 0.2ml is again made catalyzer and is shaken up, and puts into 8-12 ℃ water-bath standing and reacting 24 hours; There are a large amount of faint yellow TDZ crystal to separate out, get product 18.5 grams after the filtration, reclaim solvent in the filtrate, separate out product 1.2 grams in the mother liquor again; Actual recovery 88.74%, fusing point are 217 ℃ (decomposition).
Example 2. is got the 5-amido-1,2 of 50.5 grams, and the 3-thiadiazoles is dissolved in the tetrahydrofuran solvent of 450ml, removes by filter impurity; Add the phenylcarbimide of 60m and the triethylamine of 0.5ml and shake up, put into 12-16 ℃ water-bath standing and reacting 24 hours, have a large amount of faint yellow TDZ crystal to separate out, after the filtration product 90.3 grams; After reclaiming solvent, separate out product 5.9 grams in the mother liquor again; Actual recovery 86.67%, fusing point are 217 ℃ (decomposition).
Claims (1)
1. N-phenyl-N '-1,2, the preparation method of 3-thiadiazoles-5-urea is 5-amido-1,2,3-thiadiazoles and phenylcarbimide are catalyzer with the triethylamine in tetrahydrofuran solvent, standing and reacting 24 hours, removing desolvates obtains product; It is characterized in that described standing and reacting is to finish in 8-16 ℃ water-bath.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98112848A CN1059208C (en) | 1998-04-13 | 1998-04-13 | Preparation method of heteroatamic substituted phenyl urea |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98112848A CN1059208C (en) | 1998-04-13 | 1998-04-13 | Preparation method of heteroatamic substituted phenyl urea |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1196354A CN1196354A (en) | 1998-10-21 |
| CN1059208C true CN1059208C (en) | 2000-12-06 |
Family
ID=5222643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98112848A Expired - Fee Related CN1059208C (en) | 1998-04-13 | 1998-04-13 | Preparation method of heteroatamic substituted phenyl urea |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1059208C (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0031548A1 (en) * | 1979-12-27 | 1981-07-08 | Ube Industries, Ltd. | Process for preparing 5-amino-1,2,3-thiadiazoles |
-
1998
- 1998-04-13 CN CN98112848A patent/CN1059208C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0031548A1 (en) * | 1979-12-27 | 1981-07-08 | Ube Industries, Ltd. | Process for preparing 5-amino-1,2,3-thiadiazoles |
Non-Patent Citations (1)
| Title |
|---|
| PLANT PHYSIOL 5798-99 1976.1.1 arndt e.r等 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1196354A (en) | 1998-10-21 |
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