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Diamine derivative, process for producing the same and fungicide containing the derivative as active ingredient

A technology of diamine derivatives and compounds, which is applied in the preparation of carbamic acid derivatives, botany equipment and methods, and the preparation of organic compounds, etc., which can solve the problem that the harmfulness of useful crops with bactericidal activity is not very ideal, drug-resistant bacteria, Does not show activity and other problems, and achieves high control effect, broad spectrum of sterilization, and excellent rain resistance

Inactive Publication Date: 2007-06-20
MITSUI CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is not very satisfactory in terms of fungicidal activity or harmfulness to useful crops
In addition, due to the large-scale application of agricultural and horticultural fungicides in recent years, drug-resistant bacteria have emerged, and existing drugs may not show sufficient activity.

Method used

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  • Diamine derivative, process for producing the same and fungicide containing the derivative as active ingredient
  • Diamine derivative, process for producing the same and fungicide containing the derivative as active ingredient
  • Diamine derivative, process for producing the same and fungicide containing the derivative as active ingredient

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0167] N-[1,1-Dimethyl-2-[(4-methylbenzoyl)amino]ethyl][(1-methylethoxycarbonyl)amino]acetamide (Compound No. 14)

[0168] Add 1,1′-carbonyldi-1H-imidazole (0.25 g, 1.54mmol), stirred for 1 hour. N-(2-amino-2-methylpropyl)4-methylbenzamide (0.25 g, 1.21 mmol) was added to the reaction liquid at room temperature, and stirred at room temperature for 12 hours. The reaction solution was washed successively with 5% aqueous citric acid solution, saturated saline, saturated aqueous sodium bicarbonate, and saturated saline, and dried over anhydrous magnesium sulfate. After the inorganic salt was filtered, it was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain 0.29 g of the target product as a white solid (yield 69%).

Embodiment 2

[0170] N-[2-Methyl-1-(S)-[[(4-methylbenzoyl)amino]methyl]propyl]2-(S)-[(1,1-Dimethylethoxy Cylcarbonyl)amino]pentanamide (Compound No. 40)

[0171] At room temperature, 1,1'- Carbonyldi-1H-imidazole (1.90 g, 11.72 mmol), stirred for 1 hour. Add N-[2-(S)-amino-3-methylbutyl]4-methylbenzamide hydrochloride (2.00g, 7.79mmol), triethylamine (0.87g, 8.60 mmol), stirred at room temperature for 12 hours. The reaction solution was washed successively with 5% aqueous citric acid solution, saturated saline, saturated aqueous sodium bicarbonate, and saturated saline, and dried over anhydrous magnesium sulfate. After the inorganic salt was filtered, it was concentrated under reduced pressure, and the obtained crude product was washed with diisopropyl ether to obtain 2.86 g of the target product as a white solid (yield 88%).

Embodiment 3

[0173] N-[2-methyl-1-(S)-[[(4-methylbenzoyl)amino]methyl]propyl]2-

[0174] (S)-[(1,1-Dimethylethoxycarbonyl)amino]-2-phenylacetamide (Compound No. 60)

[0175] At room temperature, add 1 , 1'-carbonyldi-1H-imidazole (1.90 g, 11.72 mmol), stirred for 1 hour. Add N-[2-(S)-amino-3-methylbutyl]4-methylbenzamide hydrochloride (2.00g, 7.79mmol), triethylamine (0.87g, 8.60 mmol), stirred at room temperature for 12 hours. The reaction solution was washed successively with 5% aqueous citric acid solution, saturated saline, saturated aqueous sodium bicarbonate, and saturated saline, and dried over anhydrous magnesium sulfate. After the inorganic salt was filtered, it was concentrated under reduced pressure, and the obtained crude product was washed with diisopropyl ether to obtain 3.06 g of the target product as a white solid (yield 87%).

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Abstract

It is an object of the invention to provide a novel fungicide which exhibits a wide controlling spectrum against pathogens of various crops, and solves the toleration problem. The diamine derivative represented by the formula (1) and a process for preparation of the same, fungicides comprising the same as an active ingredient are disclosed: [wherein R1 is substituents such as an alkyl group having 1 to 6 carbon atoms and the like, R2 and R5 are each independently substituents such as hydrogen atom, an alkyl group having 1 to 6 carbon atoms and the like, R3 and R4 are each independently substituents such as hydrogen atom, an alkyl group having 1 to 6 carbon atoms and the like, or R3 and R4 may be bonded to each other to form a hydrocarbon ring having 3 to 6 carbon atoms, R6, R7, R8 and R9 are each independently substituents such as hydrogen atom, an alkyl group having 1 to 6 carbon atoms and the like, R10 is a substituent such as hydrogen atom, an alkyl group having 1 to 6 carbon atoms and the like, A is an oxygen atom or a sulfur atom, and Q is an aryl group or a heterocycle].

Description

technical field [0001] The invention relates to a novel diamine derivative, a preparation method thereof, and a bactericide using it as an active ingredient. Background technique [0002] Disease control plays a greater role in crop cultivation, and a variety of fungicides have been developed and utilized. However, they are not very satisfactory in terms of fungicidal activity or harmfulness to useful crops. In addition, due to the large-scale use of agricultural and horticultural fungicides in recent years, drug-resistant bacteria have emerged, and existing drugs may not show sufficient activity. Moreover, from the viewpoint of environmental problems, a new type of fungicide that is safe and capable of controlling harmful bacteria at a low concentration has been demanded. So far, WO03008372 discloses a diamine derivative different from the compound of the present invention, which is effective as a pest control agent. In contrast to the diamine derivatives described in WO...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/04C07C269/06C07C271/22C07C271/34C07C271/54C07C311/16C07C317/44C07C323/42C07C333/04C07D207/08C07D207/34C07C209/42C07D213/68C07D213/81C07D213/82C07D215/48C07D215/54C07D217/26C07D231/38C07D233/88C07D235/24C07D237/28C07D239/52C07D241/12C07D241/42C07D261/18C07D261/20C07D263/58C07D271/12C07D275/02C07D277/20C07D277/56C07D277/68C07D285/06C07D307/12C07D307/20C07D307/24C07D307/68C07D307/85C07D311/12C07D211/22C07D317/62C07D319/20C07D333/38C07D333/68C07D405/12C07D487/04A01N47/12A01N47/18A01N47/22
CPCC07D405/12C07C209/42C07C269/04C07C269/06C07C271/22C07C271/34C07C271/54C07C311/16C07C317/44C07C323/41C07C333/04C07C2101/08C07C2101/14C07C2601/08C07C2601/14A01N47/12
Inventor 垣元刚龟川尚登千叶丰河野敏之小林由实户村直文安乐城夏子吉田真子青木要治番场伸一
Owner MITSUI CHEM INC
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