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4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms

A technique of atoms and compounds, applied in the field of 4-substituted aniline derivatives

Inactive Publication Date: 2019-06-14
PI IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The effectiveness of the aniline derivatives described in the prior art is good, but leaves something to be desired in many cases

Method used

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  • 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms
  • 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms
  • 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0553] Preparation of N'-[2,5-Dimethyl-4-(phenylamino)phenyl]-N-ethyl-N-methyliminoformamide

[0554] Step A: 2,5-Dimethyl-N-phenylbenzene-1,4-diamine

[0555] To a stirred solution of 4-anilino-2,5-dimethylnitrobenzene (1.3g, 5.365mmol) in 1,4-dioxane and concentrated HCl (1:1) (30ml), add chloride Tin(II) (3.62g, 16.097mmol). The reaction mixture was heated at 100°C for 3-4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and carefully basified to pH 7-8 with sodium bicarbonate. The aqueous layer was extracted with 5% methanol / dichloromethane (3 x 100ml). The combined organic layers were washed with water (1 x 100ml), brine solution (1 x 100ml). The organic layer was dried over anhydrous sodium sulfate. Filtration and evaporation of the organic layer under high vacuum yielded a residue which was then purified by flash chromatography using 0-80% ethyl acetate:hexane as eluent to afford 2,5-dimethyl- N-Phenylbenzene-1,4-diamine...

Embodiment 2

[0559] Preparation of N'-{2,5-Dimethyl-4-[methyl(phenyl)amino]phenyl}-N-ethyl-N-methyliminoformamide

[0560] Step A: Preparation of 4-N-methylanilino-2,5-dimethylaniline

[0561] A stirred solution of p-4-N-methylanilino-2,5-dimethylnitrobenzene (2.0 g, 7.80 mmol) in 1,4-dioxane and concentrated HCl (1:1) (50 ml) , Tin(II) chloride (3.62 g, 16.097 mmol) was added. The reaction mixture was heated at 100°C for 3-4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and carefully basified to pH 7-8 with sodium bicarbonate. The aqueous layer was extracted with 5% methanol / dichloromethane (3 x 100ml). The combined organic layers were washed with water (1 x 100ml), brine solution (1 x 100ml). The organic layer was dried over anhydrous sodium sulfate. Filtration and evaporation of the organic layer under high vacuum yielded a residue which was purified by flash chromatography using 0-80% ethyl acetate:hexane as eluent to afford 4-N-methy...

Embodiment 3

[0565] Preparation of N'-[2-chloro-5-methyl-4-(phenylamino)phenyl]-N-ethyl-N-methyliminoformamide

[0566] Step A: Preparation of 4-anilino-2-chloro-5-methylaniline

[0567] p-4-anilino-2-chloro-5-methylnitrobenzene (2g, 7.61mmol), iron (2.12g, 3.80mmol) and ammonium chloride (2.1g, 3.80mmol) in ethanol-water (1: 1.50 mL) of the mixture was stirred and the solution was heated at 9°C for 2 hours. After completing the reaction, the contents were filtered through wollastonite. The filtrate was concentrated and diluted with ethyl acetate (300ml), then washed with saturated sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to obtain crude compound, which was purified by flash column chromatography to obtain 4-anilino-2-chloro-5-methylaniline as a gum (1.6 g ). LCMS(M+H)233.74

[0568] Step B: Preparation of N'-[2-chloro-5-methyl-4-(phenylamino)phenyl]-N-ethyl-N-methyliminoformamide

[0569] To a stirred solution...

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PUM

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Abstract

The invention relates to 4-substituted phenylamine derivatives of the general formula (I), wherein R1 to R8 and A have the meanings as defined in description. The invention further relates to methodsfor their preparation and use of the compounds to fight undesired phytopathogenic microorganisms, and agents for the purpose, comprising the phenylamine derivatives, all according to the invention. The invention further relates to a method for fighting undesired phytopathogenic microorganisms by application of the 4-substituted phenylamine derivatives of general formula (I) to such undesired microorganisms and / or to their habitat, according to the invention.

Description

Technical field [0001] The present invention relates to compounds intended to protect crops against undesirable phytopathogenic microorganisms. More precisely, the subject of the present invention relates to 4-substituted aniline derivatives for use in the protection of crops against undesirable phytopathogenic microorganisms. Background technique [0002] Controlling damage to crops caused by phytopathogenic microorganisms is extremely important in achieving high crop efficiency. For example, damage to ornamental, vegetable, pasture, cereal, and fruit crops by plant diseases can result in significant productivity losses and thus increased costs to consumers. Many products are commercially available to control such damage. There is a continuing need for new compounds that are more effective, less costly, less toxic, environmentally safer, or / or have a different mode of action. Certain aniline derivatives disclosed in the literature are microbicidal active ingredients in p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N37/52A01N43/40A01N43/84C07C257/12C07D265/30C07D211/12A01P3/00
CPCA01N37/52A01N43/40A01N43/84C07C257/12C07C317/32C07C323/41C07D265/30C07D211/12A01N33/26C07C211/52C07C323/48
Inventor 玛如堤·N·奈克维夏·亚修克·玛哈詹古拉伯·依克纳斯·瓦尔奴玛诺·甘帕特·卡勒维克朗·辛·贾拉苏露·G·曼住纳塔哈佳拉瓦迪·M·凡卡泰沙桑陶许·斯里达·奥卡尔鲁奇·贾克贾汀·沙曼塔亚历山大·G·M·克劳森纳康斯坦丁·波夏尼
Owner PI IND LTD
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