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A chiral bithioureido derivate containing phosphonate as well as its preparing method and use

A dithiourea derivative, chiral technology, applied in the field of chiral dithiourea derivative and its preparation

Inactive Publication Date: 2009-10-07
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method is relatively simple, it can only synthesize some symmetrical thiourea

Method used

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  • A chiral bithioureido derivate containing phosphonate as well as its preparing method and use
  • A chiral bithioureido derivate containing phosphonate as well as its preparing method and use
  • A chiral bithioureido derivate containing phosphonate as well as its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1, compound O, O'-diethylphenyl (3-((1R, 2R)-2-(3-phenylthioureido) cyclohexyl) thioureido) methylphosphonate (compound Synthesis numbered as a):

[0043] (1) O, the synthesis of O'-diethylamino (phenyl) methyl phosphonate:

[0044] Benzaldehyde (15mmol, 1.59g) and ammonia water (26%, 30mL) were added into a 50mL round bottom flask, and stirred at reflux for 3h. During this process, a white precipitate formed, which was filtered and dried. Subsequently, a 100mL three-neck round bottom flask was taken, and the dried solid was added to it, followed by diethyl phosphite (7.5mmol, 1.04g), the solid was dissolved, and refluxed at 70°C for 5h, during which an intermediate was produced. Afterwards, p-toluenesulfonic acid (5 mmol, 0.86 g) dissolved in 50 mL of tetrahydrofuran was added dropwise to the above reaction system, and stirred at 0° C. for 2 h. A large amount of solid formed which was filtered and washed with 20 mL of tetrahydrofuran. Take a 100mL round ...

Embodiment 2

[0051] Example two, compound O, O'-di-n-propylphenyl (3-((1R, 2R)-2-(3-phenylthioureido) cyclohexyl) thioureido) methylphosphonate ( Compound number is the synthesis of b):

[0052] (1) O, the synthesis of O'-di-n-propylamino (phenyl) methyl phosphonate:

[0053] Synthesize as in Example 1 (1) method and conditions. The difference is that di-n-propyl phosphite (7.5mmol, 1.25g) was added, the reaction time was 6h, and the yield was 45.9%.

[0054] (2) O, the synthesis of O' di-n-propyl isothiocyanate (phenyl) methyl phosphonate:

[0055] Synthesize as in Example 1 (2) method and conditions. The difference is that O, O'-di-n-propylamino(phenyl)methylphosphonate (6mmol, 1.63g) was added, and the yield was 61.5%.

[0056] (3) Synthesis of 1-((1R, 2R)-2-aminocyclohexyl)-3-phenylthiourea:

[0057] Synthesize as in Example 1 (3) method and conditions.

[0058] (4) Synthesis of O, O'-di-n-propylphenyl (3-((1R, 2R)-2-(3-phenylthioureido) cyclohexyl) thioureido) methylphosphonate:...

Embodiment 3

[0060] Example three, compound O, O'-diisopropylphenyl (3-((1R, 2R)-2-(3-phenylthioureido) cyclohexyl) thioureido) methylphosphonate ( Compound number is the synthesis of c):

[0061] (1) O, the synthesis of O'-diisopropylamino (phenyl) methyl phosphonate:

[0062] Synthesize as in Example 1 (1) method and conditions. The difference is that diisopropyl phosphite (7.5mmol, 1.25g) was added, the reaction time was 6h, and the yield was 50.3%.

[0063] (2) O, the synthesis of O'-diisopropyl isothiocyanate (phenyl) methyl phosphonate:

[0064] Synthesize as in Example 1 (2) method and conditions. The difference is that O,O'-diisopropylamino(phenyl)methylphosphonate (6mmol, 1.63g) was added, and the yield was 54.2%.

[0065] (3) Synthesis of 1-((1R, 2R)-2-aminocyclohexyl)-3-phenylthiourea:

[0066] Synthesize as in Example 1 (3) method and conditions.

[0067] (4) Synthesis of O, O'-diisopropylphenyl (3-((1R, 2R)-2-(3-phenylthioureido) cyclohexyl) thioureido) methylphosphonate...

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Abstract

The present invention discloses preparation method and biological activity of a compound for resisting plant virus, a chiral bithioureido derivate containing phosphonate, which has a compound structure represented by the following general formula. The invention describes a chiral bithioureido derivate containing phosphonate compounded through four-step reaction by taking chiral cyclohexanediamine, substituted isosulfocyanates, carbon disulfide, phosphorus oxychloride, triethylamine, substituted benzaldehyde, ammonia, dialkyl phosphite, p-toluenesulfonic acid and the like as raw materials. The inventive compounds a, e have higher treating inhibitory effect to tobacco mosaic virus (TMV) disease, and indicate better plant virus resisting activity; in addition, the compounds also have a certain anti-cancer activity, and can be taken as a chiral catalyst to perform asymmetric synthesis.

Description

technical field [0001] The invention relates to a chiral dithiourea derivative containing phosphonate with anti-plant virus effect and a preparation method thereof. Background technique [0002] Since the thiourea compounds thiophanate and thiophanate-methyl were put on the market as high-efficiency and low-toxicity fungicides in the late 1960s, some foreign drug companies have successfully developed several thioureas. New varieties of urea fungicides, insecticides, plant growth regulators and rodenticides, such as thiophamine as a fungicide, chloromethhiuron as an insecticide, and acaricide as a miticide Long (diafenthiuron), plant growth regulator furhenthiourea (fuphenthiourea), rodenticide Antu (antu), etc. In particular, this type of compound has the advantages of low residue, low phytotoxicity, and low acute toxicity to mammals. Therefore, its molecular design, synthesis, and biological activity research are a hot spot in the creation of green pesticides today. [00...

Claims

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Application Information

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IPC IPC(8): C07F9/40A01P1/00A61P35/00B01J31/02
Inventor 胡德禹杨璇宋宝安杨松李向阳薛伟金林红陈卓
Owner GUIZHOU UNIV
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