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A kind of 2-(3-oxo-2-pentylcyclopentyl)acetamide derivative and its application

A technology of pentylcyclopentyl and acetamide, which is applied in the chemical field, can solve the problems affecting the marketing of drugs and the few types of plant-induced disease resistance activators, and achieve good plant-induced disease resistance activity, novel structure, and good safety Effect

Active Publication Date: 2022-05-06
SHENYANG RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There are few types of plant-induced disease resistance activators in the market, and there are certain problems in their activity and cost, which affects the market promotion of such drugs

Method used

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  • A kind of 2-(3-oxo-2-pentylcyclopentyl)acetamide derivative and its application
  • A kind of 2-(3-oxo-2-pentylcyclopentyl)acetamide derivative and its application
  • A kind of 2-(3-oxo-2-pentylcyclopentyl)acetamide derivative and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Embodiment 1: the synthesis of compound 1-4

[0102]

[0103] Add 3.0 g of 2-(3-oxo-2-pentylcyclopentyl)acetic acid, 3.0 g of oxalyl chloride, 150 mL of dichloromethane, and three drops of DMF (N,N-dimethylformamide) into a 250 mL flask. The reaction was stirred at room temperature for 12 hours. After the reaction was completed, the solvent was removed under reduced pressure, and 150 mL of ethyl acetate, 1.5 g of p-toluidine, and 2.0 g of triethylamine were added. The reaction was stirred at room temperature for 2 hours. After the reaction was monitored by TLC, wash with 50mL×3 water, dry the organic phase with anhydrous sodium sulfate for 12 hours, precipitate under reduced pressure, and perform column chromatography (eluent is ethyl acetate and petroleum ether (boiling range 60-90°C) , the volume ratio is 1:6) to obtain 2.3 grams of compound 2-(3-oxo-2-pentylcyclopentyl)acetyl 4-methylaniline as a white solid.

Embodiment 2

[0104] Embodiment 2: the synthesis of compound 1-4

[0105]

[0106] In a 250mL flask, add 3.0 grams of 2-(3-oxo-2-pentylcyclopentyl)acetic acid, EDCI (1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride ) 5.0 grams, triethylamine 2.0 g, p-toluidine 1.5 grams, dichloromethane 150 mL. The reaction was stirred at room temperature for 12 hours. After completion of the reaction, wash with 50 mL×3 of water, dry the organic phase with anhydrous sodium sulfate for 12 hours, precipitate under reduced pressure, and perform column chromatography (eluent is ethyl acetate and petroleum ether (boiling range 60-90° C.), volume The ratio is 1:6) to obtain 1.7 g of the compound 2-(3-oxo-2-pentylcyclopentyl)acetyl-p-toluidine as a white solid.

[0107] Other compounds shown in formula I can also be obtained according to the above synthetic route, and the characterization data of other compounds are as follows:

[0108] Compounds 1-3:

[0109] 1 H NMR (600MHz, Chloroform-d) δ7.62(...

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Abstract

The invention belongs to the chemical field, specifically a kind of 2-(3-oxo-2-pentylcyclopentyl) acetamide derivatives such as the compound shown in formula I, and the compound shown in formula I in the preparation of plant growth regulator agent or plant-induced disease resistance activator. The compound of the invention has a novel structure, and at the same time, the compound has good plant induction and disease resistance activity. Moreover, the compound of the general formula has a good activity of inhibiting seed germination at a high concentration, and is very safe (it can still have a good germination activity under high concentration treatment), without causing the seeds to lose their germination activity.

Description

technical field [0001] The invention belongs to the field of chemistry, specifically a 2-(3-oxo-2-pentylcyclopentyl)acetamide derivative, and the application of said compound for regulating plant growth or inducing and activating plant disease resistance . Background technique [0002] Plant growth regulators (PGRs) are generally any substance or mixture of substances used to accelerate or retard the rate of growth or maturation or to alter the development of a plant or its products. PGRs affect plant growth and differentiation. More specifically, various plant growth regulators (PGRs) can, for example, reduce plant height, stimulate seed germination, cause flowering, deepen leaf coloration, alter plant growth rate and alter the timing and efficiency of fruit set. Plant growth regulators (PGRs) can exhibit pronounced growth-regulating properties that can lead to increased yields of cultivated plants or harvested crops. Plant growth regulators (PGRs) have concentration-dep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/74A01N37/42A01N43/40A01N43/08A01N43/10A01N43/54A01N43/58A01N43/60C07D213/75C07D333/36C07D307/66C07D239/42C07D241/20C07D237/20A01P21/00
CPCC07C235/74A01N37/42A01N43/40A01N43/08A01N43/10A01N43/54A01N43/58A01N43/60C07D213/75C07D333/36C07D307/66C07D239/42C07D241/20C07D237/20C07C2601/08
Inventor 周繁冉兆晋魏婷婷李继广王芳焦姣王远柴宝山赵宪成
Owner SHENYANG RES INST OF CHEM IND
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