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 irratio

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

Example Embodiment

[0040] Example 1

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

[0042]

[0043] (1) Add 1,3-dichloroacetone (1mol) to 1L of 2M hydrochloric acid ether solution at 25°C, then add tert-butyl nitrite (1mol), continue the reaction at 25°C for 10h, and remove after the reaction is complete After cooling, the crude product of the compound represented by the formula (2-2) is obtained by cooling diethyl ether, which is washed with 1-chlorobutane, filtered, and the filter cake is collected; and the filtrate is recrystallized, filtered, and the filter cake is dried to obtain the formula (2 -2) The compound represented by the formula (2-2) is obtained by combining the two batches to obtain the pure product of the compound represented by formula (2-2).

[0044] (2) At 25°C, add sodium bicarbonate (5mol) to 1L of the compound represented by formula (2-2) (1mol) in methylene chloride solution, then add 2,6-difluorostyrene (1mol) ...

Example Embodiment

[0048] Example 2

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

[0050]

[0051] At 0℃, sodium hydride (1.5mmol) was added to the 10mL DMF solution of the compound (1.2mmol) represented by formula (11), reacted at 0℃ for 0.5h, and then added with formula (2-1) Compound (1mmol), the reaction was continued at 25°C for 6h. After the reaction is completed, the compound represented by formula (1) is obtained through extraction, washing, concentration, and column chromatography purification.

[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= 13.8Hz,1H),4.07(d,J=13.8Hz, 1H), 3.81(dd,J=17.4,12.0Hz,1H), 3.64(dd,J=17.4,9.0Hz,1H), 3.37–3.26 ( m, 2H), 3.02 (q, J = 7.8 Hz, 2H), 2.85 (t, J = 12.6 Hz, 1H), 2.23 (d, J = 13.8 Hz, 1H), 2.16 (d, ...

Example Embodiment

[0054] Example 3

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

[0056]

[0057] Under the condition of 0℃, sodium hydride (1.5mmol) was added to the 10mL DMF solution of the compound (1.2mmol) represented by formula (21), reacted at 0℃ for 0.5h, and then added as shown by formula (2-1) Compound (1mmol), the reaction was continued at 25°C for 6h. After the reaction is completed, the compound represented by formula (2) is obtained through extraction, washing, concentration, and column chromatography purification.

[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 = 7.8 Hz, 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 = 16.8 Hz, 1H), 5.36 (d, J = 16.8 Hz, 1H), 4.35 (d, J = 13.2 Hz, 1H), 4.13 (d, J = 13.2 Hz, 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 = 16.2 Hz, 2H), 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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