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Application of a 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound as a fungicide

A technology of adamantanecarboxylate and benzoyloxy is applied in the application field of 1-adamantanecarboxylate-2-(substituted benzoyloxy)ethyl ester compounds as fungicides, which can solve structural and biological problems. Activity studies have not found any problems such as literature reports

Active Publication Date: 2021-03-23
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The series of 1-adamantanecarboxylic acid-2-(substituted benzoyloxy)ethyl ester compounds designed and synthesized by the present invention have no literature reports on their structure and biological activity research

Method used

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  • Application of a 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound as a fungicide
  • Application of a 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound as a fungicide
  • Application of a 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound as a fungicide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Synthesis of Derivative Ia (R(n)=H):

[0027] Dissolve 1.5 mmol of benzoyl chloride in 5 mL of tetrahydrofuran to prepare a solution (5 mL) of benzoyl chloride (1.5 mmol) in tetrahydrofuran.

[0028] The intermediate 2-hydroxyethyl-1-adamantanecarboxylate (0.336 g, 1.5 mmol), tetrahydrofuran (10 mL) and acid-binding agent triethylamine (1.8 mmol) were mixed, stirred and dissolved, and placed in an ice bath A solution of benzoyl chloride (1.5 mmol) in tetrahydrofuran (5 mL) was slowly added dropwise. After the dropwise addition, react at room temperature for 2 h, then filter to remove the hydrochloride of triethylamine generated by the reaction, and remove the solvent tetrahydrofuran by rotary evaporation of the filtrate obtained by filtration, and separate the obtained rotary evaporation residue through column chromatography (eluent is The mixed solution of ethyl acetate and sherwood oil with a volume ratio of 1:5) to obtain a light yellow oily liquid, which ...

Embodiment 2

[0031] Example 2 Synthesis of derivative Ib (R(n)=o-fluorine):

[0032] The intermediate 2-hydroxyethyl-1-adamantanecarboxylate (0.336 g, 1.5 mmol), tetrahydrofuran (8.5 mL) and acid-binding agent triethylamine (2.25 mmol) were mixed, stirred and dissolved, and placed in an ice bath A solution of o-fluorobenzoyl chloride (1.5 mmol) in tetrahydrofuran (4 mL) was slowly added dropwise. After the dropwise addition was completed, react at room temperature for 3 h, then filter to remove the hydrochloride of triethylamine generated by the reaction, and remove the solvent tetrahydrofuran by rotary evaporation of the filtrate obtained by filtration, and separate the obtained rotary evaporation residue through column chromatography (eluent: The mixed solution of ethyl acetate and sherwood oil of volume ratio 1: 3) obtains white waxy solid, is 1-adamantanecarboxylic acid-2-(2-fluorobenzoyloxy group) ethyl ester, and its yield is calculated as 64.9%.

[0033] 1 H NMR (500 MHz, CDCl 3...

Embodiment 3

[0035] Example 3 Synthesis of derivative Ic (R(n)=p-fluorine):

[0036] The intermediate 2-hydroxyethyl-1-adamantanecarboxylate (0.336 g, 1.5 mmol), tetrahydrofuran (8.5 mL) and acid-binding agent triethylamine (2.0 mmol) were mixed, stirred and dissolved, and placed in an ice bath A solution (4 mL) of p-fluorobenzoyl chloride (1.5 mmol) in tetrahydrofuran was slowly added dropwise. After the dropwise addition was completed, react at room temperature for 3 h, then filter to remove the hydrochloride of triethylamine generated by the reaction, and remove the solvent tetrahydrofuran by rotary evaporation of the filtrate obtained by filtration, and separate the obtained rotary evaporation residue through column chromatography (eluent: The mixed solution of ethyl acetate and sherwood oil of volume ratio 1: 3) obtains white waxy solid, is 1-adamantanecarboxylic acid-2-(4-fluorobenzoyloxy) ethyl ester, and its yield is calculated as 55.7%.

[0037] 1 H NMR (500 MHz, CDCl 3 ) δ ...

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Abstract

The invention discloses applications of a 1-adamantanecarboxylic acid-2-(substituted benzoyloxy)ethyl ester compound as bactericides, wherein the 1-adamantanecarboxylic acid-2-(substituted benzoyloxy)ethyl ester compound has a structure represented by a formula (I), H on the benzene ring is mono-substituted or di-substituted with a substituent R or is not substituted, n is an integer of 0-2, preferably 1-2, and represents the number of the substituents R on the benzene ring, the H on the benzene ring is not substituted when n is 0, the H on the benzene ring is mono-substituted by the substituent R when n is 1, the H on the benzene ring is di-substituted by the substituent R when n is 2, the substituents R at different substitution positions are the same or different, and the substituents Rare hydrogen, C1-C3 alkoxy, C1-C2 haloalkyl, and halogen. According to the present invention, the 1-adamantanecarboxylic acid-2-(substituted benzoyloxy)ethyl ester compound particularly has good inhibition effect on Alternaria solani, Fusarium graminearum, Sclerotinia sclerotiorum, Botrytis cinerea and other fungi.

Description

technical field [0001] The invention relates to the application of a 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound as a fungicide. Background technique [0002] Adamantane has unique chemical and physical properties, and has been used in pesticides (Chemical Reagents, 2016, 38(03): 224-230), medicine (Chemical Reviews, 2013, 113(5): 3516-3604), optoelectronics Materials (Tetrahedron, 2013, 69(48): 10357-10 360) and other fields. According to literature reports, adamantane derivatives have bactericidal (Journal of Organic Chemistry, 1999, 64(24): 8916-8921, Organic Chemistry, 2014, 34(12): 2543-2550), insecticidal (Chinese Journal of Chemistry, 2011, 31(4): 486-489), herbicide (Energetic Materials, 2017, 25(01): 76-85, Fine Chemical Information, 1986(10): 11-14), etc. more and more attention. In addition, adamantane is generally considered to provide special lipophilicity, so the introduction of adamantane structure can enhance the lipophilici...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N37/10A01N37/40A01P3/00C07C69/78C07C67/14C07C67/56C07C69/92
CPCA01N37/10A01N37/40C07C67/14C07C67/56C07C69/78C07C69/92C07C2603/74
Inventor 翁建全孔瑶蕾庞凯胜刘幸海
Owner ZHEJIANG UNIV OF TECH
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