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Hexahydro-phthalmide compound, its preparation and use thereof

A technology of hexahydrophthalimide and compound is applied in the field of preparation of bactericides, can solve the problems of toxic and side effects, unfriendly environment of bactericides, etc., and achieves the effects of simple preparation method, good bactericidal spectrum and wide range of raw materials

Active Publication Date: 2007-07-18
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Hexahydro-phthalmide compound, its preparation and use thereof
  • Hexahydro-phthalmide compound, its preparation and use thereof
  • Hexahydro-phthalmide compound, its preparation and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Example 1: Preparation of N-(4,6-bismethylpyrimidin-2-yl)-1,2,3,4,5,6-hexahydrophthalimide (I-1) Weighing 1, 152 mg (1 mmol) of 2,3,4,5,6-hexahydrophthalic anhydride was placed in a 25 mL round bottom flask, 10 mL of chloroform was added, and 123 mg of 2-amino-4,6-bismethylpyrimidine (1 mmol) was added thereto. 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 172mg of white solid. Yield 62%. Its physical and chemical data are as follows: [ 1 H] NMR (400MHz, CDCl 3 ): δ / ppm; 7.055 (s, 1H, H-pyrimidine), 3.060-3.037 (t, J 1 = 4.381Hz,J 2 =4.578Hz, 2H, 2CH), 2.517(s, 6H, 2CH 3 ), 1.919 (br.m, 4H, 2CH 2 ), 1.533-1.478 (m, 4H, 2CH 2 ). Mp. 182-183°C.

Embodiment 2

[0040] Example 2: Preparation of N-(6-methylpyridin-2-yl)-1,2,3,4,5,6-hexahydrophthalimide (I-4) Weigh 3,4,5 152 mg (1 mmol) of 6-tetrahydrophthalic anhydride was placed in a 25 mL round bottom flask, 10 mL of trimethylbenzene was added, and 108 mg of 2-amino-6-methylpyridine (1 mmol) was added thereto. 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 177mg of white solid. Yield 73%. 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

[0041] Example 3: The reaction temperature was maintained 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 67%, and the physical and chemical data of the product were the same as in Example 1.

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Abstract

A hexahydro-phthaimide compound, its production and use are disclosed. The process is carried out by reacting compound in structural formula II with compound in structural formula III to obtain compound in structural formula I at 80-150 DEG C. under existing of single solvent or mixed solvent in inactive solvent, 1,4-dioxane, dichloromethane, chloroform, furanidine, methylbenzene and trimethyl benzene, choosing R1 from hydroxy, phobic, alkyl, SCN, N3, aryl, heterary and fused heterary independently, and choosing R2 and R3 from H atom, hydroxy, phobic, halogen atom, SCN, alkyl, alkoxy, N3, aryl, heterary and fused heterary independently. X is N atom or CH. It has rational structure and is simple. It can be used for insecticide.

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): C07D401/04C07D403/04A01N43/38A01N43/40A01N43/54A01P3/00
Inventor 席真班树荣陈文彬李康施捷王勇
Owner NANKAI UNIV