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Compound with fused heterocycle structure as well as preparation method and application thereof and fungicide

A compound and fused heterocyclic ring technology, applied in the field of pesticides, fungicides and fungicides, can solve the problems of prolonged use time, irrational use, pathogenic bacteria resistance, etc., and achieve the effect of good market development prospects and excellent control effects.

Active Publication Date: 2020-02-21
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the prolonged use of these fungicides and long-term irrational use, many pathogenic bacteria have developed serious drug resistance.

Method used

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  • Compound with fused heterocycle structure as well as preparation method and application thereof and fungicide
  • Compound with fused heterocycle structure as well as preparation method and application thereof and fungicide
  • Compound with fused heterocycle structure as well as preparation method and application thereof and fungicide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] This example is used to illustrate the preparation method of the compound represented by formula (2-1).

[0042]

[0043] (1) At 25°C, add 1,3-dichloroacetone (1mol) into 1L of 2M diethyl ether hydrochloride solution, then add tert-butyl nitrite (1mol), continue the reaction at 25°C for 10h, and remove Diethyl ether, after cooling, obtain the crude product of the compound shown in formula (2-2), and wash with 1-chlorobutane, filter, collect filter cake; And the filtrate is recrystallized, filter, also obtain formula (2 The compound shown in -2) was combined to obtain the pure product of the compound shown in formula (2-2) after merging two batches.

[0044] (2) At 25°C, add sodium bicarbonate (5mol) to 1L of the compound (1mol) shown in formula (2-2) in dichloromethane solution, then add 2,6-difluorostyrene (1mol) Add slowly, continue to stir and react for 4h, after the reaction is completed, filter and remove the solvent in the filtrate to obtain the compound repre...

Embodiment 2

[0049] This example is used to illustrate the preparation method of the compound represented by formula (1).

[0050]

[0051] At 0°C, add sodium hydride (1.5mmol) to a 10mL DMF solution of the compound (1.2mmol) represented by formula (11), react at 0°C for 0.5h, and then add the compound represented by formula (2-1) Compound (1 mmol), continue to react at 25°C for 6h. After completion of the reaction, extract, wash, concentrate, and purify by column chromatography to obtain the compound shown in formula (1).

[0052] White solid, yield 89%, m.p.128-130℃, 1 H NMR (600MHz, CDCl 3 )δ8.51 (dd, J=4.8,1.6Hz,1H),8.06(dd,J=8.4,1.6Hz,1H),7.67(s,1H),7.36–7.28 (m,1H),7.10(dd ,J=8.4,4.8Hz,1H),6.92(t,J=8.4Hz,2H),6.08(dd,J=12.0,9.0Hz,1H),5.39(s,2H),4.62(d,J= ( m, 2H), 3.02(q, J=7.8Hz, 2H), 2.85(t, J=12.6Hz, 1H), 2.23(d, J=13.8Hz, 1H), 2.16(d, J=13.8Hz, 1H), 1.90–1.75(m, 2H), 1.41(t, J=7.8Hz, 3H). 13 CNMR (151MHz, CDCl 3 )δ174.36, 165.09, 162.04(d, J=5.1Hz), 160.37(d, J=5.1Hz), ...

Embodiment 3

[0055] This example is used to illustrate the preparation method of the compound represented by formula (2).

[0056]

[0057] At 0°C, add sodium hydride (1.5mmol) into a 10mL DMF solution of the compound (1.2mmol) represented by formula (21), react at 0°C for 0.5h, and then add the compound represented by formula (2-1) Compound (1 mmol), continue to react at 25°C for 6h. After completion of the reaction, extract, wash, concentrate, and purify by column chromatography to obtain the compound shown in formula (2).

[0058] White solid, yield 79%, m.p.165-166℃, 1 H NMR (600MHz, DMSO-d 6 )δ 8.48(s,1H),8.31(d,J=7.8Hz,1H),8.04(s,1H),7.55–7.45(m,1H),7.27–7.07(m,3H),6.05–5.95( m,1H),5.46(d,J=16.8Hz,1H),5.36(d,J=16.8Hz,1H),4.35(d,J=13.2Hz,1H),4.13(d,J=13.2Hz, 1H),3.91(t,J=14.4Hz, 1H),3.54(dd,J=17.4,8.4Hz,1H),3.36–3.24(m,3H),2.81(t,J=12.6Hz, 1H), 2.10(t, J=16.2Hz, 2H), 1.78(d, J=14.4Hz, 1H), 1.57(t, J=12.6Hz, 1H), 1.36(d, J=6.6Hz, 6H). 13 C NMR (101MHz, DMSO-d 6 )δ175.08,165.1...

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Abstract

The invention relates to the field of pesticide fungicides and discloses a compound with a fused heterocycle structure as well as a preparation method and application thereof and a fungicide. The compound with the fused heterocycle structure has a structure of a formula (1), a formula (2) or a formula (3). The compound disclosed by the invention has excellent prevention and control effects on plant diseases caused by oomycete pathogenic bacteria such as phytophthora, phytophthora capsicum, phytophthora ultimate, phytophthora tobacco, phytophthora lychee and phytophthora cucumber, is remarkablyprior to an ordinary oomycete disease and insect prevention and treatment chemical dimethomorph, and has good market development prospects.

Description

technical field [0001] The invention relates to the field of pesticide fungicides, in particular to a compound containing a fused heterocyclic structure and a preparation method thereof, the application of the compound containing a fused heterocyclic structure in the prevention and treatment of plant oomycete diseases, and the compound containing a fused heterocyclic structure Application as a pesticide fungicide and a fungicide. Background technique [0002] Oomycete is one of the important pathogenic bacteria that cause plant diseases. It has the characteristics of wide parasitic range, strong destructiveness, great damage, and rapid development. It can harm most major economic crops such as potatoes, tomatoes, peppers, grapes, tobacco, and peppers. Wait. Simultaneously, the disease that it causes is also more difficult to control, therefore brings great loss to agricultural production. [0003] The main plant pathogens of oomycetes include Phytophthora infestans, Phytop...

Claims

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Application Information

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IPC IPC(8): C07D471/04A01N43/78A01P3/00
CPCC07D471/04A01N43/78C07D471/02C07D417/04
Inventor 杨光富李建龙
Owner HUAZHONG NORMAL UNIV
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