Arylamino isobutyryl derivative and application thereof

An aroylaminoisobutyryl derivative and alkylaminocarbonyl technology, which is applied in the field of chemistry and can solve the problems of few types of plant-induced disease resistance activators, affecting drug market promotion and the like.

Active Publication Date: 2020-05-26
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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  • Arylamino isobutyryl derivative and application thereof
  • Arylamino isobutyryl derivative and application thereof
  • Arylamino isobutyryl derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0161] Embodiment 1: the synthesis of compound 1-49

[0162]

[0163] In a 250mL flask, add 7.0 grams of 4-fluoro-2-chlorobenzoic acid, 10.0 grams of EDCI (1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride), aminoisobutyric acid 7.5 grams of methyl ester hydrochloride, 150 mL of dichloromethane, and 5 mL of triethylamine. The reaction was stirred at room temperature for 12 hours. After the reaction was completed, the reaction liquid was washed with 50 mL×3 of water, the organic phase was dried with anhydrous sodium sulfate for 12 hours, precipitated under reduced pressure, 150 mL of ethanol and 7.0 g of sodium hydroxide were added, and the reaction was stirred at room temperature for 2 hours. After the completion of the reaction as monitored by TLC, desolvation under reduced pressure, add 100 mL of water to the residue, extract with ethyl acetate 50 mL × 3, dry the organic phase with anhydrous sodium sulfate for 12 hours, desolvate under reduced pressure, column c...

Embodiment 2

[0164] Embodiment 2: the synthesis of compound 4-7

[0165]

[0166] In a 250mL flask, add 3.1 grams of compound 4-fluorobenzamidoisobutyric acid (synthesized with reference to Example 1), EDCI (1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride Salt) 3.0 g, dichloromethane 150 mL. The reaction was stirred at room temperature for 12 hours. After the reaction was completed, the reaction solution was washed with 100 mL of water × 3, the organic phase was dried with anhydrous sodium sulfate for 12 hours, precipitated under reduced pressure, and the residue was column chromatographed (eluent was ethyl acetate and petroleum ether (boiling range 60-90 °C), the volume ratio is 1:4) to obtain the compound 2-(4-fluorophenyl)-4,4-dimethyl-2-oxazolin-5-one, 1.6 g of white solid.

[0167]

[0168] Into a 250 mL flask were added 1.0 g of the compound 2-(4-fluorophenyl)-4,4-dimethyl-2-oxazolin-5-one, 1.5 g of ethylamine, and 150 mL of tetrahydrofuran. The reaction was stirr...

Embodiment 3

[0169] Embodiment 3: the synthesis of compound 17-7

[0170]

[0171] Into a 250 mL flask were added 2.0 g of the compound 4-fluorobenzamidoisobutyric acid (synthesized with reference to Example 1), 4.0 g of oxalyl chloride, and 150 mL of dichloromethane. The reaction was stirred at room temperature for 12 hours. After the reaction was completed, the reaction solution was washed with 100 mL of water × 3, the organic phase was dried with anhydrous sodium sulfate for 12 hours, precipitated under reduced pressure, and the residue was column chromatographed (eluent was ethyl acetate and petroleum ether (boiling range 60-90 °C), the volume ratio is 1:4) to obtain the compound 2-(4-fluorophenyl)-4,4-dimethyl-2-oxazolin-5-one, 1.1 g of white solid.

[0172]

[0173] Into a 250 mL flask were added 1.0 g of the compound 2-(4-fluorophenyl)-4,4-dimethyl-2-oxazolin-5-one, 1.5 g of cyclohexylamine, and 150 mL of tetrahydrofuran. The reaction was stirred at room temperature for 12 h...

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PUM

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Abstract

The invention belongs to the field of chemistry, and particularly relates to an arylamino isobutyryl derivative and application thereof in regulating plant growth and inducing activation of plant disease resistance. The arylamino isobutyryl derivative is a compound shown as a formula I. The compound disclosed by the invention is novel in structure; and meanwhile, the compound has relatively good plant-induced disease-resistant activity. And the compound as shown in the general formula has good seed germination inhibition activity at high concentration, has good safety (still has good germination activity under high-concentration treatment), and does not cause seed germination activity loss.

Description

technical field [0001] The invention belongs to the field of chemistry, and specifically relates to an aroylamino isobutyryl derivative and its use for regulating plant growth and 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-dependent growth inhibitory eff...

Claims

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Application Information

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IPC IPC(8): C07C233/83C07C235/52C07C255/57C07D213/81C07D213/82C07D307/68C07D333/38C07D239/28C07D241/24C07D237/24A01N37/46A01N43/40A01N43/10A01N43/08A01N43/54A01N43/60A01N43/58A01P21/00A01P1/00A01P3/00
CPCC07C233/83C07C235/52C07C255/57C07D213/81C07D213/82C07D307/68C07D333/38C07D239/28C07D241/24C07D237/24A01N37/46A01N43/40A01N43/10A01N43/08A01N43/54A01N43/60A01N43/58
Inventor 周繁冉兆晋王远柴宝山王芳魏婷婷崔顺艳李继广
Owner SHENYANG RES INST OF CHEM IND
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