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3-substituted phenylamidine compounds, preparation and use thereof

A compound, C3-C8- technology, applied in the field of crop protection agents to achieve the effect of enhancing antimicrobial activity

Pending Publication Date: 2021-09-28
PI IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The benzamidine derivatives described in the prior art work well, but in various cases still have deficiencies

Method used

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  • 3-substituted phenylamidine compounds, preparation and use thereof
  • 3-substituted phenylamidine compounds, preparation and use thereof
  • 3-substituted phenylamidine compounds, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0503] Example 1: Synthesis of 3-bromoamidine intermediate (III):

[0504] a) N'-(3-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylformimide (III)

[0505] Step 1: Preparation of 3-bromo-2,5-dimethylbenzoic acid (XXIV)

[0506] A mixture of 2,5-dimethylbenzoic acid (2g, 13.3mmol) and sulfuric acid (20mL) was cooled to 0°C, and N-bromosuccinimide (2.4g, 13.3mmol) was added to the reaction at 0°C in the mixture for 1.5 hours. After the reaction was completed, the reaction mixture was poured onto crushed ice and extracted with ethyl acetate (50 mL). The ethyl acetate layer was washed with brine solution, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography (using 50% ethyl acetate in hexane as eluent) to give 3-bromo-2,5-dimethylbenzoic acid (1.6 g, 52% yield). LCMS(M-1):229.00.

[0507] Step 2: Preparation of tert-butyl (3-bromo-2,5-dimethylphenyl)carbamate

[0508] Anhydrous The reaction mixture in ...

example 2

[0527] Example 2: Preparation of N'-(3-benzyl-2,5-dimethylphenyl)-N-ethyl-N-methylformimide

[0528] a) N'-(2,5-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N - Preparation of ethyl-N-methylformimide

[0529] N'-(3-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylformamide (1.0g, 3.7mmol), bis(pinacol)diboron (1.9g , 7.4mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane[PdCl2(dppf)-CH2Cl2] (0.2g, 0.2mmol) and potassium acetate (0.7 g, 7.4 mmol) in 1,1'-dioxane (30 ml) stirred the mixture and degassed with nitrogen for 5 minutes. The reaction mixture was stirred at 95 °C under nitrogen for 16 hours. After the reaction was complete, the reaction mixture was diluted with dichloromethane, filtered through a bed of celite, and the residue was washed with dichloromethane (100 mL). The combined filtrates were washed with brine solution and dried over anhydrous sodium sulfate. Volatiles were removed under reduced pressure. The crude pr...

example 3

[0532] Example 3: Preparation of N-ethyl-N'-(3-(3-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimide

[0533] a) Preparation of 4-methyl-2-nitro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

[0534] 2-Bromo-4-methyl-6-nitroaniline (2.00g, 8.7mmol), bis(pinacol) diboron (4.4g, 17.3mmol), [1,1'-bis(diphenyl Phosphino)ferrocene] dichloropalladium(II) dichloromethane [PdCl2(dppf)-CH2Cl2] (0.35g, 0.4mmol) and potassium acetate (2.1g, 21.6mmol) stirred mixture of 1,4-diox The alkane (30 mL) solution was degassed with nitrogen. The reaction mixture was stirred at 95 °C under nitrogen for 16 hours. After the reaction was complete, the reaction mixture was diluted with dichloromethane, filtered through a bed of celite, and the residue was washed with dichloromethane (100 mL). The combined filtrates were washed with brine solution, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by column chromatograp...

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Abstract

The present invention disclosed 3-substituted phenylamidine compounds of general formula (I), wherein R1, R2, R3, R4, R4a, R4b, A and E have the same meanings as defined in description. The present invention further discloses methods for their preparation and use of the compounds of general formula (I) as a crop protection agent.

Description

technical field [0001] The present invention relates to 3-substituted benzamidine compounds. More specifically, the present invention relates to 3-substituted benzamidine compounds of general formula (I), their preparation methods and their use as crop protection agents. Background technique [0002] Fungal pathogens continue to pose a serious threat to public health and agriculture. Therefore, control of plant diseases caused by fungal plant pathogens is extremely important for achieving high crop yields. Plant diseases can lead to significant reductions in productivity of ornamental, vegetable, pasture, cereal and fruit crops, thereby increasing costs to consumers. In addition to being often highly destructive, plant diseases can be difficult to control and can render pathogens resistant to commercial fungicides. Many products are commercially available to control this damage, but there is a need for new compounds that are more effective, less costly, less toxic, enviro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/23C07C255/61C07C211/52C07C251/24C07D213/58C07C255/58A01N37/52A01N43/40A01N43/54A01N43/60A01N43/78C07D213/74C07D239/42C07D241/12C07D241/20C07D277/64
CPCC07D213/74C07D213/58C07D239/42C07D241/12C07D241/20C07D277/64A01N37/52A01N43/40A01N43/54A01N43/60A01N43/78C07C251/24C07C255/61C07C211/52C07C323/23C07C255/58C07C249/02C07C253/02C07C319/14C07C209/68A01N37/34A01P3/00A01N43/32A01N47/40C07C251/06C07C253/30C07C319/02C07D319/20
Inventor 马鲁蒂·奈克维沙·A·马哈詹S·西瓦库马尔基肖尔·辛格·拉索德萨钦·纳纳特·贡姆桑托什·什里达尔·奥特加鲁芝·加尔嘉哈加拉瓦迪·M·文卡泰莎亚历山大·G·M·克劳泽纳
Owner PI IND LTD
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