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A kind of nitroguanidine compound and its preparation and application

A compound, the technology of nitroguanidine, which is applied in the field of nitroguanidine compounds and their preparation and application, can solve problems such as negative environmental impact

Active Publication Date: 2021-09-10
SHANGHAI UNIV OF ENG SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it is undeniable that with the long-term use of fungicides, bacteria have continuously increased their resistance to such fungicides through heredity and mutation from generation to generation.
In addition, due to frequent and continuous use, it also has a certain negative impact on the environment

Method used

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  • A kind of nitroguanidine compound and its preparation and application
  • A kind of nitroguanidine compound and its preparation and application
  • A kind of nitroguanidine compound and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Taking 1-[(S-benzyl-S-methyl)sulfoxide base]-2 nitro-3-propyl nitroguanidine as an example, the nitroguanidines shown in the formula (I) provided by the present invention are set forth Compound preparation methods.

[0032] 1-[(S-benzyl-S-methyl-S-oxo)sulfide]-2nitro-3-propylnitroguanidine (in formula I, R 1 is propyl, R 2 For the synthesis of 2-chlorophenyl), the following preparation methods are specifically adopted:

[0033] (a) N, the synthesis of -propyl nitroguanidine

[0034]

[0035]Add 5.0 g (0.048 mol) of nitroguanidine and 50 ml of anhydrous DMF into a 100 mL three-necked flask, stir until the nitroguanidine is completely dissolved, and cool to 0° C. in an ice bath. Add 2.32g (0.058mol) of 60% sodium hydride three times, and keep the reaction temperature not exceeding 10°C. After reacting for 1 hour, slowly add 7.27g (0.058mol) of 98% 1-bromopropane dropwise. Remove the ice bath and react overnight. The reaction solution was poured into 300 mL of wate...

Embodiment 2

[0051] In addition to step (a), the added organic solvent D is DMSO, the alkaline substance is sodium ethylate, the catalytic reaction temperature is 80 ° C, and the catalytic reaction time is 12h. The compound of structure shown in nitroguanidine and general formula (II) The molar ratio is 1:1.5, in step (b), the added organic solvent A is methanol, the reaction temperature is 50°C, the reaction time is 20h, the molar ratio of the compound of the structure shown in general formula (IV) to sodium methyl mercaptide 1.5:1, the organic solvent B added in the step (c) is ethanol, the oxidant A is hydrogen peroxide, the oxidation reaction temperature is 50°C, and the oxidation reaction time is 20h, the compound of the structure shown in the general formula (Ⅴ) and the general formula ( Ⅲ) The molar ratio of the compound with the structure shown in the oxidant is 1.5:1:1.5. In step (d), the organic solvent C added is ethanol, the oxidant B is potassium permanganate, the oxidation rea...

Embodiment 3

[0053] In addition to step (a), the basic substance added is sodium methylate, the catalytic reaction temperature is 30°C, the catalytic reaction time is 5h, and the molar ratio of nitroguanidine to the compound of the structure shown in the general formula (II) is 1:1.5 , step (b) outside, the organic solvent A that adds is DMF, and reaction temperature is 20 ℃, and reaction time is 1h, and the molar ratio of the compound of structure shown in general formula (Ⅳ) and sodium methyl mercaptide is 1.5:1, step The organic solvent B added in (c) is DMSO, the oxidant A is sodium hypochlorite, the oxidation reaction temperature is 30 DEG C, the oxidation reaction time is 15h, the compound of the structure shown in the general formula (Ⅴ) and the structure shown in the general formula (Ⅲ) The molar ratio of the compound to the oxidizing agent is 1.5:1:1.5. In step (d), the organic solvent C added is DMSO, the oxidizing agent B is sodium dichromate, the oxidation reaction temperature i...

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Abstract

The present invention relates to a nitroguanidine compound and its preparation and application. The nitroguanidine compound is a compound having a structure represented by general formula (I), or a pharmaceutically acceptable salt, enantiomer, or pharmaceutically acceptable salt thereof. Diastereoisomers, tautomers, solvates, polymorphs or prodrugs: wherein, R1 is C1-C8 saturated or unsaturated aliphatic hydrocarbon group, benzyl, substituted benzyl or substituted picolyl R2 is one of C1-C8 saturated or unsaturated aliphatic hydrocarbon groups, phenyl, substituted phenyl groups or substituted pyridyl groups. Compared with the prior art, the nitroguanidine compounds of the present invention are effective against Fusarium, Gibberella, Solanum solani, Phytophthora, Pythium melon and fruit, Botrytis cinerea, Sclerotinia, Rhizoctonia solani etc. It has good control effect on fungal diseases and can be used as a potential plant fungicide.

Description

technical field [0001] The invention relates to the technical field of agricultural chemicals, in particular to a nitroguanidine compound and its preparation and application. Background technique [0002] Crops including rice, tomato, potato, wheat, etc. are prone to fungal diseases, such as rice bakanae disease (Gibberella), tomato gray leaf spot (Solanum solani), potato late blight (Phytophthora), taro blight (Phytophthora These fungal diseases are mainly transmitted through the soil, and the crops will inevitably be infected with the corresponding fungal diseases when they grow on the soil infected with such bacteria. Therefore, it is necessary to spray carbendazim, frost powder or Mianfengbao and other fungicides. However, it is undeniable that with the long-term use of fungicides, bacteria have continuously increased their resistance to such fungicides through heredity and mutation from generation to generation. In addition, due to frequent and continuous use, it also...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C381/10C07D213/61A01N47/44A01P3/00
CPCA01N47/44C07C381/10C07D213/61
Inventor 李洪森邵群肖玉龙赵琳静程聪聪侯宇欣马佳慧俞彦岚韦发彩
Owner SHANGHAI UNIV OF ENG SCI
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