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Oxime ether (ester) compound as well as preparation method and application thereof

A technology of compound and oxime ether, applied in the field of pathogenic bacteria control, to achieve the effect of novel structure, broad-spectrum bactericidal activity and obvious effect

Active Publication Date: 2021-12-21
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report of introducing 1,2,3,4-tetrahydroquinoline and indole into the skeleton structure of oxime ethers (esters). Therefore, the present invention discloses a novel class of 1,2, Oxime ether (ester) compounds of 3,4-tetrahydroquinoline or indole and their application as agricultural fungicides

Method used

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  • Oxime ether (ester) compound as well as preparation method and application thereof
  • Oxime ether (ester) compound as well as preparation method and application thereof
  • Oxime ether (ester) compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1: Preparation of compound 2-fluorobenzaldehyde O-(1,2,3,4-tetrahydroquinoline-1-carbonyl)oxime (I-01)

[0053]

[0054] Add 0.6957 g (5 mmol) of 2-fluorobenzaldehyde oxime and 10 mL of dichloromethane into a 25 mL single-necked bottle, and stir at room temperature. Then, a solution of 0.9783 g (5 mmol) of 1,2,3,4-tetrahydroquinoline-1-formyl chloride in 5 mL of dichloromethane was added dropwise thereto, and the reaction was continued for 300 min after the dropwise addition was completed. Purified by column chromatography (petroleum ether: ethyl acetate = 15:1), after drying, 0.9695 g of light yellow solid was obtained, yield 65%, melting point: 98-100°C, 1 H NMR (500MHz, CDCl 3 )δ8.60(s,1H),8.09–8.06(m,1H),7.68(d,J=8.1Hz,1H),7.45(m,1H),7.20(t,J=7.6Hz,2H), 7.09 (m, 3H), 3.88–3.86 (m, 2H), 2.82 (t, J=6.6Hz, 2H), 2.04–1.99 (m, 2H).

Embodiment 2

[0055] Example 2: Preparation of compound 3-methylbenzaldehyde O-(1,2,3,4-tetrahydroquinoline-1-carbonyl)oxime (I-10)

[0056]

[0057] Add 0.6759 g (5 mmol) of 3-methylbenzaldehyde oxime, 0.5060 g (5 mmol) of triethylamine, and 10 mL of toluene into a 25 mL single-necked bottle at room temperature. Then, a 5 mL toluene solution of 0.9783 g (5 mmol) of 1,2,3,4-tetrahydroquinoline-1-carbonyl chloride was added dropwise thereto, and the reaction was continued for 5 minutes after the dropwise addition was completed. Purified by column chromatography (petroleum ether: ethyl acetate = 10:1), and dried to obtain 0.8831 g of a yellow solid, yield 60%, melting point: 88-90°C, 1 H NMR (500MHz, CDCl 3 )δ8.29(s,1H),7.68(d,J=8.2Hz,1H),7.63(s,1H),7.48(d,J=7.4Hz,1H),7.30(dd,J=14.6,7.2 Hz, 2H), 7.20(t, J=7.7Hz, 1H), 7.13(d, J=7.0Hz, 1H), 7.06(dd, J=11.0, 3.7Hz, 1H), 3.88–3.85(m, 2H ), 2.81(t, J=6.6Hz, 2H), 2.38(s, 3H), 2.03–2.00(m, 2H), 13 C NMR (125MHz, CDCl 3 )δ 155.38, 153.19, 138...

Embodiment 3

[0058] Example 3: Preparation of compound 3-phenoxybenzaldehyde O-(1,2,3,4-tetrahydroquinoline-1-carbonyl)oxime (I-16)

[0059]

[0060] Add 1.0662 g (5 mmol) of 3-phenoxybenzaldoxime, 0.3955 g (5 mmol) of pyridine, and 10 mL of ethyl acetate into a 25 mL single-necked bottle, and stir at -20°C. Then 1,2,3,4-tetrahydroquinoline-1-formyl chloride 1.1739g (6mmol) in 5mL ethyl acetate solution was added dropwise thereto, and the reaction was carried out for 120min after the dropwise addition was completed. Purified by column chromatography (petroleum ether: ethyl acetate = 10:1), and dried to obtain 1.2290 g of a yellow solid, yield 66%, melting point: 76-78 °C, 1 H NMR (500MHz, CDCl 3 )δ8.27(s,1H),7.65(d,J=8.0Hz,1H),7.48(d,J=7.7Hz,1H),7.36(dt,J=15.3,8.0Hz,4H),7.18( t,J=7.9Hz,1H),7.11(q,J=7.1Hz,3H),7.03(dd,J=23.9,7.6Hz,3H),3.85–3.83(m,2H),2.80(t,J =6.6Hz, 2H), 2.01(q, J=6.4Hz, 2H), 13 C NMR (125MHz, CDCl 3 )δ157.87, 156.70, 154.80, 153.03, 137.71, 132.10, 130.58, 130.25, ...

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Abstract

The invention belongs to the technical field of pathogenic bacteria control, and particularly relates to an oxime ether (ester) compound as well as a preparation method and application thereof. According to the invention, a 1, 2, 3, 4-tetrahydroquinoline or indole fragment with excellent biological activity is introduced into an oxime ether (ester) compound to obtain a compound with a novel structure. The structure of the compound is shown as a formula I. The compound has broad-spectrum bactericidal activity, particularly has an obvious inhibition effect on rhizoctonia solani, botrytis cinerea and valsa mali, and can be used as a bactericide for preventing and treating plant diseases.

Description

technical field [0001] The invention belongs to the technical field of pathogen control, and in particular relates to an oxime ether (ester) compound, a preparation method and an application. Background technique [0002] The use of pesticides can not only reduce food losses caused by diseases, insects, and weeds, but also have certain benefits in improving the quality of food. However, with the massive and partly irrational use of pesticides, it brings great benefits as well as certain negative effects, such as resistance and environmental problems. Therefore, it is urgent to develop new green pesticides with high efficiency, broad spectrum and environmental friendliness to replace some existing varieties. [0003] Oxime ether (ester) compounds have excellent biological activity, their medical value has been widely reported, and their agricultural activity has a good research basis. Among them, among the commercialized pesticide varieties, oxime ether (ester) compounds ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/08C07D209/08A01N47/24A01N43/38A01P3/00
CPCC07D215/08C07D209/08A01N47/24A01N43/38Y02A50/30
Inventor 雷鹏穆雅利胡夏桐王宇佳马志卿冯俊涛王勇王艺博
Owner NORTHWEST A & F UNIV
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