1, 2, 4-oxadiazole derivative containing 1, 3, 4-thiadiazole unit as well as preparation method and application of 1, 2, 4-oxadiazole derivative

A technology of oxadiazole and thiadiazole, which is applied in the fields of chemical industry and pesticides, can solve the problems of no nematicidal activity, low nematicidal activity in vitro, and lack of flexibility.

Active Publication Date: 2022-03-18
GUIZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned patents have the following disadvantages: First, in the derivatives containing 1,2,4-oxadiazole structure, no compound with broad-spectrum nematicidal activity has been found, only for root-knot nematode incognita, amides The compound is also only against root-knot nematode incognita, and other plant parasitic nematodes have not been evaluated, and the above-mentioned thiophene compounds have shown i...

Method used

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  • 1, 2, 4-oxadiazole derivative containing 1, 3, 4-thiadiazole unit as well as preparation method and application of 1, 2, 4-oxadiazole derivative
  • 1, 2, 4-oxadiazole derivative containing 1, 3, 4-thiadiazole unit as well as preparation method and application of 1, 2, 4-oxadiazole derivative
  • 1, 2, 4-oxadiazole derivative containing 1, 3, 4-thiadiazole unit as well as preparation method and application of 1, 2, 4-oxadiazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Example 1: 2-fluoro-N-(5-(((3-phenyl-1,2,4-oxadiazol-5-yl)methyl)sulfur)-1,3,4-thiadiazole -2-yl) benzamide (i.e. compound 4a) preparation method, comprising the following steps:

[0064] (1) Preparation of N-hydroxybenzamide:

[0065] Hydroxylamine hydrochloride (4.04g, 58.18mmol), sodium hydroxide (2.33g, 58.18mmol), and ethanol (48.49mL) were mixed in a 100mL three-necked flask, and benzonitrile (5.00g, 48.49mmol) was added at room temperature, and heated after dropping Reflux for 7 hours; after the reaction, the reaction system was washed with water, separated, dried, suction filtered and desolvated under reduced pressure to obtain 5.50 g of N-hydroxybenzamide intermediate, with a yield of 83.31%;

[0066] (2) Preparation of 5-(chloromethyl)-3-phenyl-1,2,4-oxadiazole:

[0067] Chloroacetyl chloride (6.84g, 60.59mmol) was added dropwise into a mixed solution of N-hydroxybenzamide (5.50g, 40.40mmol) and 40.40mL of toluene under ice bath, and the temperature was rais...

Embodiment 2

[0072] Example 2: N-(5-((3-phenyl-1,2,4-oxadiazol-5-yl)methyl)thio)-1,3,4-thiadiazol-2-yl ) the preparation method of cyclopropanecarboxamide (being compound 4b), comprises the following steps:

[0073] Steps (1)~(3) are with embodiment 1;

[0074] (4) The target compound N-(5-((3-phenyl-1,2,4-oxadiazol-5-yl)methyl)thio)-1,3,4-thiadiazole-2- Base) the preparation of cyclopropanecarboxamide:

[0075] 5-((3-Phenyl-1,2,4-oxadiazol-5-yl)methyl)thio)-1,3,4-thiadiazol-2-amine (0.20g, 0.69mmol) , triethylamine (0.17g, 1.72mmol) and 2.07mL of dry dichloromethane were added to the one-necked bottle, cyclopropylformyl chloride (86.11mg, 0.82mmol) was added dropwise into the system, and the reaction was carried out at room temperature for 6h; the solvent was removed under reduced pressure , recrystallized from methanol to give white solid N-(5-((3-phenyl-1,2,4-oxadiazol-5-yl)methyl)thio)-1,3,4-thiadiazole- 2-yl)cyclopropanecarboxamide 0.16g, yield 64.85%.

Embodiment 3

[0076] Example 3: 4-methoxy-N-(5-(((3-phenyl-1,2,4-oxadiazol-5-yl)methyl)thio)-1,3,4- The preparation method of thiadiazol-2-yl)benzamide (i.e. compound 4c), comprises the following steps:

[0077] Steps (1)~(3) are with embodiment 1;

[0078] (4) The target compound 4-methoxy-N-(5-(((3-phenyl-1,2,4-oxadiazol-5-yl)methyl)thio)-1,3,4 - Preparation of thiadiazol-2-yl)benzamide:

[0079] 5-((3-Phenyl-1,2,4-oxadiazol-5-yl)methyl)thio)-1,3,4-thiadiazol-2-amine (0.20g, 0.69mmol) , triethylamine (0.17g, 1.72mmol) and 2.07mL of dry dichloromethane were added to the one-necked bottle, p-methoxybenzoyl chloride (0.14g, 0.82mmol) was added dropwise into the system, and the reaction was carried out at room temperature for 6h; The solvent was removed and recrystallized from methanol to obtain a white solid 4-methoxy-N-(5-(((3-phenyl-1,2,4-oxadiazol-5-yl)methyl)thio)-1 ,3,4-Thiadiazol-2-yl)benzamide 0.15g, the yield was 51.36%.

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Abstract

The invention relates to the field of chemical engineering and pesticides, in particular to a 1, 2, 4-oxadiazole derivative containing a 1, 3, 4-thiadiazole unit and a preparation method and application of the 1, 2, 4-oxadiazole derivative. The 1, 2, 4-oxadiazole derivative of the 1, 3, 4-thiadiazole unit is applied to preparation of pharmaceutical preparations or pharmaceutical compositions for preventing and treating plant nematodes such as meloidogyne incognita, pine wood nematodes, aphelenchoides besseyi and caenorhabditis elegans, and the derivative is simple in structure and preparation process and low in production cost.

Description

technical field [0001] The present invention relates to the fields of chemical engineering and pesticides, in particular to 1,2,4-oxadiazole derivatives containing 1,3,4-thiadiazole units, and to the 1,3,4-thiadiazole derivatives containing 1,3,4-thiadiazole units , A preparation method of 2,4-oxadiazole derivatives, and the application of the derivatives in medicines for preventing and treating plant diseases such as root-knot nematode incognita, pine wood nematode and rice stem-point nematode. Background technique [0002] Plant nematode disease is one of the most widely distributed and seriously harmful infectious diseases, which not only seriously threatens global food security but also seriously affects agricultural production, and brings huge losses to agricultural production. The losses caused are more than 157 billion U.S. dollars. At the same time, the economic losses caused by nematode diseases in my country are as high as 70 billion yuan (about 11 billion U.S. doll...

Claims

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Application Information

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IPC IPC(8): C07D417/06A01N43/836A01P5/00
CPCC07D417/06A01N43/82
Inventor 甘秀海刘丹曾华南袁婷王正兴梁峻铖罗领耿望
Owner GUIZHOU UNIV
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