(E)-methyl 2-methoxyiminobenzeneacetate compound containing 1, 2, 4-triazole and preparation method and application thereof

A technology of methoxyimino and methyl phenylacetate, which is applied in the field of compounds and their preparation, and can solve problems such as low safety, environmental pollution, and monotony

Inactive Publication Date: 2014-09-24
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Bactericides include traditional multi-site fungicides and modern selective fungicides. Generally speaking, the former has many sites of action and a broad spectrum of bacteria, but is less safe and easy to pollute the environment. The latter has a site of action Specificity, relatively simple, safe and efficient

Method used

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  • (E)-methyl 2-methoxyiminobenzeneacetate compound containing 1, 2, 4-triazole and preparation method and application thereof
  • (E)-methyl 2-methoxyiminobenzeneacetate compound containing 1, 2, 4-triazole and preparation method and application thereof
  • (E)-methyl 2-methoxyiminobenzeneacetate compound containing 1, 2, 4-triazole and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of Example 1.3-aryl-4-amino-5-mercapto-1,2,4-s-triazole

[0031] (1) Synthesis of Benzohydrazide

[0032] Add 15g of ethyl benzoate to a 50mL round bottom flask, add ethanol, add 10mL of 85% hydrazine hydrate after stirring and dissolving the solid (when adding hydrazine hydrate at the beginning, the system often turns brownish yellow, gradually turns green, and with heating, finally become a colorless transparent liquid), heated to reflux for 4 hours, cooled and distilled off excess ethanol, a large amount of solids precipitated, filtered, and recrystallized with ethanol to obtain a white needle-like solid, which was dried to obtain 12.6 g of the product. Yield: 92.6%.

[0033] (2) Synthesis of benzoylhydrazine dithioformic acid potassium salt

[0034] Add 8g of benzohydrazide, 30mL of absolute ethanol, and 1:1.2 times KOH with benzohydrazide to a 100mL three-necked flask, stir and dissolve, then add 1:1 times of CS in an ice bath 2 , warming up to reflux ...

Embodiment 2

[0037] Example 2. Preparation of 3-mercapto-4-substituted phenylimino-5-phenyl-4H-1,2,4-s-triazole (II)

[0038] (1) Preparation of 3-mercapto-4-phenylimino-5-phenyl-4H-1,2,4-s-triazole (II-a)

[0039] In a 50mL single-necked round bottom flask, add 1.39g (10mmol) of 3-aryl-4-amino-5-mercapto-1,2,4-s-triazole, 1.06g (10mmol) of benzaldehyde, 30mL of absolute ethanol and Add 3 drops of glacial acetic acid, heat, reflux, and monitor by TLC. After the reaction was complete, cool to room temperature, filter with suction, and recrystallize with ethanol to obtain white rod-shaped crystals.

[0040] (2) Preparation of 3-mercapto-4-p-methoxyphenylimino-5-phenyl-4H-1,2,4-s-triazole (II-b) In a 50mL single-neck round bottom flask, Add 1.39 g (10 mmol) of 3-aryl-4-amino-5-mercapto-1,2,4-s-triazole, 1.36 g (10 mmol) of 4-methoxybenzaldehyde, 30 mL of absolute ethanol and 3 drops of ice Acetic acid, heating, reflux, TLC monitoring. After the reaction was complete, cool to room temperat...

Embodiment 3

[0047]Example 3. Target compound (E)-2-(3-(4-(E)-2-substituted benzylideneamino-5-phenyl-4H-1,2,4-triazole-3-mercapto )-methylene)-phenyl)-3-methoxyiminoacetic acid methyl ester (Ia-Iv) preparation

[0048] (1) (E)-2-(3-(4-(E)-2-benzylideneamino-5-phenyl-4H-1,2,4-triazole-3-mercapto)-methylene Base)-phenyl)-3-methoxyiminoacetic acid methyl ester (I-a) preparation

[0049] Weigh 0.490g (1.75mmol) 3-mercapto-4-phenylimino-5-phenyl-4H-1,2,4-s-triazole 0.474g (1.75mmol) (E)-2-(2 -Bromomethyl)phenyl-3-methoxyiminoacetic acid methyl ester, 0.24g (1.75mmol) K 2 CO 3 , dissolved in 15ml DMF, and reacted at 80°C for 1h. Cool to room temperature, add 30mL of water, precipitate solid, filter with suction, recrystallize by heating with ethanol (a small amount), and filter with suction to obtain a white solid.

[0050] (1)(E)-2-(3-(4-(E)-2-p-methoxybenzylideneamino-5-phenyl-4H-1,2,4-triazole-3-mercapto )-methylene)-phenyl)-3-methoxyiminoacetic acid methyl ester (I-b) preparation

[...

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Abstract

The invention discloses a novel compound with bactericidal activity and provides a preparation method and application of the compound. The compound is an (E)-methyl 2-methoxyiminobenzeneacetate compound containing 1, 2, 4-triazole. The preparation method includes the step that the compound is formed by making a compound represented by a general formula II and a compound represented by a general formula III react. The compound has good bactericidal activity and can be applied to preparation of crop bactericide.

Description

technical field [0001] The present invention relates to compounds and their preparation methods and uses, in particular to a class of (E)-methoxyiminophenylacetic acid methyl ester compounds with bactericidal activity containing 1,2,4-triazole and their preparation Methods and uses. Background technique [0002] Food is of great significance to human survival, development and social stability, and the use of pesticides can effectively increase food production. While pesticides have made great contributions to human civilization, highly toxic and high-residue pesticides have also brought negative impacts on the environment on which human beings depend. With the progress of society and the improvement of civilization, people and nature are required to live in harmony, and people have put forward higher requirements for pesticides. Therefore, research and development of green pesticides with high efficiency, low toxicity, easy degradation, safety and environmental compatibilit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12A01N43/653A01P3/00
CPCA01N43/653C07D249/12
Inventor 王献友贡东军庞艳苹陈培云赵志磊吴广臣
Owner HEBEI UNIVERSITY
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