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Phenazino-1-carboxylic acid triazole derivative as well as preparation method and application thereof

A technology of triazole derivatives and suzinomycin, which is applied in the field of pesticide compound preparation and achieves the effect of novel chemical structure and high commercialization prospect

Active Publication Date: 2020-03-13
上海沪联生物药业(夏邑)股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, although phenazine-1-carboxylic acid has a certain broad-spectrum antibacterial activity, there is still room for improvement in its antibacterial activity, and it is necessary to further develop pesticide compounds with higher antibacterial activity for use as fungicides

Method used

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  • Phenazino-1-carboxylic acid triazole derivative as well as preparation method and application thereof
  • Phenazino-1-carboxylic acid triazole derivative as well as preparation method and application thereof
  • Phenazino-1-carboxylic acid triazole derivative as well as preparation method and application thereof

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preparation example Construction

[0018] For the second solution of the present invention, the present invention proposes a kind of synthetic method of Shenzimycin triazole derivatives, comprising the following steps: synthesizing phenazine-1-carbonyl chloride, synthesizing substituted (3-(benzylthio) )-1H-1,2,4-triazole, synthesis of substituted (3-(benzylthio)-1H-1,2,4-triazol-1-yl)(phenazin-1-yl)methanone .

[0019] The synthesis method of the above-mentioned Shenzimycin triazole derivatives is used to synthesize the Shenzimycin triazole derivatives in the first solution of the present invention.

[0020] It should be noted that in the above synthesis process, the order of synthesizing phenazine-1-carbonyl chloride and synthesizing substituted (3-(benzylthio)-1H-1,2,4-triazole can be interchanged.

[0021] Wherein, the above-mentioned synthesis of phenazine-1-carbonyl chloride is to react with sphenazine and oxalyl chloride as raw materials, and the reaction formula is as follows:

[0022]

[0023] Whe...

Embodiment 1

[0030] This embodiment provides a shenazine triazole derivative, which is the compound a02 in Table 1 and Table 2, prepared by the following steps: (1) phenazine-1-carbon Synthesis of acid chlorides

[0031] 2.24g (0.01mol) Shenzimycin, 100ml CH 2 Cl 2 Put it in a 250ml beaker, add 1.57g (0.012mol) oxalyl chloride and 3 drops of DMF dropwise with a dropper, install a condenser tube and a drying tube, turn off the condensed water, heat up to 50°C, stir and reflux for 12h, and spin the resulting solution dry, with CH 2 Cl 2 Dissolved and then spin-dried to obtain 2.2 g of a yellow-brown solid with a yield of 92%.

[0032]

[0033] (2) Synthesis of 3-((4-methylbenzyl)thio)-1H-1,2,4-triazole.

[0034] Dissolve 2.02g (0.02mol) of 1H-1,2,4-triazole-3-thiol in a 250ml flask filled with 20ml of NaOH (4%), add 50ml of absolute ethanol, stir, and heat at 75°C for reaction , add 3.36g (0.024mol) p-methylbenzyl chloride dropwise when the color becomes lighter, keep the temperatur...

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PUM

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Abstract

The invention discloses a phenazino-1-carboxylic acid triazole derivative as well as a preparation method and application thereof. The phenazine-1-carboxylic acid triazole derivative is a substituted(3-(benzylthio)-1H-1, 2, 4-triazole-1-yl) (phenazine-1-yl) ketone compound, and has a structure disclosed in the invention, wherein X is one or more of H, C1-C4 straight-chain or branched-chain alkyl,halogen, nitro, cyano, phenyl, trifluoromethyl, trichloromethyl and methoxy substituent. According to the invention, phenazino-1-carboxylic acid is used as a parent structure and is subjected to active substructure splicing with 1H-1, 2, 4-triazole-3-mercaptan to synthesize a series of new compounds, the chemical structure is novel, and the compounds can be used for preventing and treating rice sheath blight disease, tomato early blight, watermelon fusarium wilt, wheat scab, rice blast and pepper blight; bioassay results show that the bactericidal activity of most of the compounds on certainpathogenic fungi is superior to that of parent compound phenazino-1-carboxylic acid, and the compounds have a relatively promising commercialization prospect.

Description

technical field [0001] The invention relates to the technical field of preparation of pesticide compounds, in particular to a Shenzimycin triazole derivative and its preparation method and application. Background technique [0002] Shenqinmycin (shenqinmycin) chemical name is phenazine-1-carboxylic acid (PCA), which is a new type of microbial pesticide independently developed by Shanghai Jiaotong University. It has the characteristics of high efficiency, safety, and broad spectrum. Its main component is fluorescent Phenazine-1-carboxylic acid, a secondary metabolite produced by Pseudomonas M18. More than 1,000 phenazine-1-carboxylic acid analogs have been discovered and confirmed in structure, indicating that they exist widely in nature. Biological activity studies have found that phenazine-1-carboxylic acid and its analogues have significant medical and agricultural activities, and have excellent characteristics of low toxicity to humans and animals and easy degradation. ...

Claims

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Application Information

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IPC IPC(8): C07D403/06A01N43/653A01P3/00
CPCA01N43/653C07B2200/13C07D403/06
Inventor 徐志红张卫李俊凯
Owner 上海沪联生物药业(夏邑)股份有限公司
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