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1,2,4-triazole compound containing oxime carboxylate, and preparation method and application thereof

A compound, carboxylic acid oxime technology, applied in the direction of botany equipment and methods, applications, chemicals for biological control, etc., to achieve good biological activity effect

Active Publication Date: 2016-08-10
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the other hand, the long-term application of chemical pesticides has led to the increasingly prominent problem of drug resistance of plant pathogens, and the resulting increase in the amount of pesticides used and the reduction of drug efficacy have an increasing impact on the ecological environment.

Method used

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  • 1,2,4-triazole compound containing oxime carboxylate, and preparation method and application thereof
  • 1,2,4-triazole compound containing oxime carboxylate, and preparation method and application thereof
  • 1,2,4-triazole compound containing oxime carboxylate, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment 1: the synthesis of propane-2-ketone O-(2-(3-phenyl-4-amino-1,2,4-triazole-5-thio)acetyl) oxime (compound number is I 1 )

[0056] (1) Dissolve 5.81 g (100.00 mmol) of anhydrous acetone in 100 mL of absolute ethanol, add 20.73 g (150.00 mmol) of anhydrous potassium carbonate and 10.42 g (150.00 mmol) of hydroxylamine hydrochloride, and stir at room temperature for 8 hours. After the reaction, the solvent was evaporated under reduced pressure, washed with water, and dried to obtain 6.15 g of white needle-like crystals, with a yield of 84%.

[0057] (2) Dissolve 7.31 g (100.00 mmol) of acetone oxime in 70 mL of anhydrous acetone, add 15.20 g (110.00 mmol) of anhydrous potassium carbonate, and slowly drop 12.42 g of chloroacetyl chloride diluted with anhydrous acetone in an ice bath. g (110.00mmol), continue stirring for about 2 hours after the dropwise addition, pour the reaction solution into 150 mL of water, separate the liquid, filter, and wash with water t...

Embodiment 2

[0063] Example 2: (Z, E)-butane-2-one O-(2-(3-phenyl-4-amino-1,2,4-triazole-5-thio)acetyl)oxime Synthesis (compound number is I 2 )

[0064] (1) Synthesized under the conditions and method of (1) in Example 1, except that 7.21 g (100.00 mmol) of butanone was added.

[0065](2) Synthesized under the conditions and methods of (2) in Example 1, except that 8.71 g (100.00 mmol) of butanone oxime was added.

[0066] (3) Synthesis under the conditions and methods of (3) in Example 1.

[0067] (4) Synthesize as in the conditions and methods of (4) in Example 1.

[0068] (5) Synthesize as in the conditions and methods of (5) in Example 1.

[0069] (6) Synthesize as in the conditions and methods of (6) in Example 1.

[0070] (7) Synthesized under the same conditions and methods as in (7) in Example 1, except that 0.36 g (2.20 mmol) of (Z,E)-butan-2-one O-(2-chloroacetyl)oxime was added.

Embodiment 3

[0071] Embodiment 3: the synthesis of propane-2-ketone O-(2-(3-(4-fluorophenyl)-4-amino-1,2,4-triazole-5-thio)acetyl)oxime ( The compound number is I 3 )

[0072] (1) Synthesize as in the conditions and methods of (1) in Example 1.

[0073] (2) Synthesis under the conditions and methods of (2) in Example 1.

[0074] (3) Synthesized under the conditions and methods of (3) in Example 1, except that 7.01 g (50.00 mmol) of 4-fluorobenzoic acid was added.

[0075] (4) Synthesized according to the conditions and methods of (4) in Example 1, except that 6.73 g (40.00 mmol) of ethyl 4-fluorobenzoate was added.

[0076] (5) Synthesized according to the conditions and methods of (5) in Example 1, except that 4.62 g (30.00 mmol) of 4-fluorobenzohydrazide was added.

[0077] (6) Synthesized under the same conditions and methods as in (6) in Example 1, except that 3.92 g (20.00 mmol) of 2-(4-fluorophenyl)-5-mercapto-1,3,4-oxadiazole was added.

[0078] (7) Synthesized as in Example 1 ...

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Abstract

The invention discloses a 1,2,4-triazole compound containing oxime carboxylate, and a preparation method and application thereof. The general formula (I) of the compound is described in the specification. In the formula (I), R is selected from a group consisting of a phenyl group, a 4-fluorophenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, a 4-nitrophenyl group, a 4-methoxyphenyl group, a 3,4-dimethyoxyphenyl group and a 3,4,5-trimethoxyphenyl group; R1 is a methyl group or ethyl group; and R2 is a methyl group. The compound provided by the invention has good biological activity in inhibition of Xanthomonas axonopodis pv.citri, Ralstonia solanacearum and Xanthomonas oryzae pv.oryzae.

Description

technical field [0001] The present invention relates to the technical field of chemical engineering, in particular to a 1,2,4-triazole compound containing carboxylic acid oxime ester, and at the same time relates to the preparation of the 1,2,4-triazole compound containing carboxylic acid oxime ester The preparation method and the application of the 1,2,4-triazole compound containing carboxylic acid oxime lipid in anti-plant bacteria. Background technique [0002] The occurrence and spread of plant diseases directly affect the quality and yield of agricultural products, and chemical control is still one of the main countermeasures at present. 1,2,4-Triazole compounds have various biological activities such as antibacterial, antiviral, and anticancer. Tebuconazole and Propiconazole have been widely used in the control of agricultural diseases. In recent years, the excellent biological activities of oxime lipid compounds in antibacterial, antiviral and insecticidal aspects...

Claims

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Application Information

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IPC IPC(8): C07D249/12A01N43/653A01P1/00
CPCA01N43/653C07D249/12
Inventor 薛伟朱雪松谢艳王晓斌肖维黄民国钟新敏贺鸣卢平柳敏
Owner GUIZHOU UNIV
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