Imide analog compounds and its preparation method

A compound and imide technology, applied in the field of preparation of fungicides, can solve the problems of toxic and side effects, unfriendly environment of fungicides, etc., and achieve the effects of simple preparation method, good bactericidal spectrum, and low cost of synthesis process

Active Publication Date: 2007-08-15
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] But some of these fungicides are not friendly to the environment and have toxic side effects on humans
Moreover, long-term use will cause the strain to develop obvious resistance

Method used

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  • Imide analog compounds and its preparation method
  • Imide analog compounds and its preparation method
  • Imide analog compounds and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: Preparation of N-(4,6-bismethylpyrimidin-2-yl)-3,4,5,6-tetrahydrophthalimide (I-1)

[0041] Weigh 152 mg (about 1 mmol) of 3,4,5,6-tetrahydrophthalic anhydride and place it in a 25 mL round bottom flask, add 10 mL of chloroform, and then add 123 mg of 2-amino-4,6-bismethylpyrimidine (about 1 mmol ). The reaction temperature was maintained at 80°C. Stir for 12 hours, column chromatography (40g silica gel H, 2% CH 3 OH / CH 2 Cl 2 elution) to obtain 171mg of white solid. Yield 62%. Its physical and chemical data are as follows: [ 1 H] NMR (400MHz, CDCl 3 ): δ / ppm; 6.991(s, 1H, H-Pyrimidine), 2.470(s, 6H, 2CH 3 ), 2.335 (m, 4H, 2CH 2 ), 1.725 (m, 4H, 2CH 2 ).Mp.141-143℃.

Embodiment 2

[0042] Example 2: Preparation of N-(6-methylpyridin-2-yl)-3,4,5,6-tetrahydrophthalimide (I-5)

[0043] Weigh 152 mg (about 1 mmol) of 3,4,5,6-tetrahydrophthalic anhydride into a 25 mL round bottom flask, add 10 mL of trimethylbenzene, and then add 108 mg of 2-amino-6-methylpyridine (about 1 mmol). The reaction temperature was maintained at 150°C. Stir for 10 hours, column chromatography (40g silica gel H, 2% CH 3 OH / CH 2 Cl 2 Elution) to obtain 97mg of white solid. Yield 40%. Its physical and chemical data are as follows: [ 1 H] NMR (400MHz, CDCl 3 ): δ / ppm; 7.703-7.664 (t, J 1 =7.750Hz,J 2 =7.731Hz, 1H, Py), 7.172-7.153(d, J=7.667Hz, 1H, Py), 7.018-6.998(d, J=7.787Hz, 1H, Py), 3.033-3.011(m, 2H, 2CH ), 2.545 (s, 3H, CH 3 ), 1.885 (br.s, 4H, 2CH 2 ), 1.478-1.471 (m, 4H, 2CH 2 ).Mp.92-94°C.

Embodiment 3

[0044] Example 3: The reaction temperature was kept at 110° C., and 10 mL of chloroform was added instead of 10 mL of toluene. The other reaction conditions were the same as in Example 1, the yield was 63%, and the physical and chemical data were the same as in Example 1.

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Abstract

The invention relates to imide compounds and method for preparation, which comprises, maintaining reaction temperature at 80-150 deg. C, at the presence of one single solvent selected from inert solvent, 1,4-dioxane, methylene chloride, chloroform, tetrahydrofuran, toluene and trimethylbenzene or their mixed solvent, reacting compound having a structural formula II with compound having a structural formula III to obtain compound having a structural formula I, wherein R1 separately selected from hydroxy, mercapto, alkyl, SCN, N3, aryl, heteroaryl, R2, R3 are separately selected from H atom, hydroxy, mercapto, halogen atom, SCN, alkyl, alkoxy, N3, aryl, heteroaryl, X is N atom or CH.

Description

technical field [0001] The invention relates to an imide compound, especially an imide compound used in the preparation of a fungicide, and a preparation method thereof. Background technique [0002] There are many reports of imide compounds as bactericides, and some are commercialized, such as: captan (captan), folpet (folpet), tetrachlordane (Captafol), Yipu Tong. (Iprodione) and Vinclozolin, etc.: [0003] [0004] But some of these fungicides are not friendly to the environment and have toxic side effects on people. And long-term use will cause the strain to develop obvious resistance. Therefore, designing and synthesizing fungicides with high efficiency, low toxicity, broad spectrum, high selectivity, low residue and low resistance is an urgent problem in the current pesticide research. Contents of the invention [0005] The invention provides an imide compound, which has bactericidal activity and can be applied to the preparation of bactericides. [0006] The ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04C07D401/04A01N43/40A01N43/54A01P3/00C07D209/48C07D239/42C07D213/16
Inventor 席真班树荣王勇陈文彬李康施捷
Owner NANKAI UNIV
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