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Application of 3,6-disubstituted imidazo[1, 2-b] pyridazine derivatives in preparation of fungicides

A technology of disubstituted imidazole and 2-b, applied in the field of pesticides, can solve problems such as unresearched inhibitory effects, and achieve the effect of strong bactericidal activity and broad-spectrum bactericidal activity

Active Publication Date: 2020-06-05
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the abuse of fungicides, it also leads to the cross-resistance of plant pathogenic fungi to fungicides [Ma Z, MichailidesTJ. Crop Prot. 2005; 24:853–863]. Novel fungicides with bacteriostatic activity are important in securing agricultural production
[0003] The pyridazine ring is an important heterocyclic skeleton, and molecules containing this skeleton have various pharmacological activities, such as anticancer, antibacterial, antifungal, antituberculosis, antiinflammatory, antipyretic, antidiabetic, insecticidal, and antihypertensive et al [Kolar P, Tisler M. Adv. Hererocycl. Chem. 1999, 75:167-241], [Bendjeddou LZ, N, Villiers B, Prina E, G F, Galons H, Meijer L, Oumata. Eur. J. Med. Chem. 2017, 125, 696-709] reported that the imidazo[1,2-b] pyridazine ring was used as Cdk 2, pim, IKKB, abl, VEGFR 2 and SYK protein kinase inhibitors, some imidazo[1,2-b]pyridazine derivatives in the prior art have been used in the research of antitumor drugs, but such derivatives have not been used for plant pathogenic fungi to study the inhibitory effect of

Method used

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  • Application of 3,6-disubstituted imidazo[1, 2-b] pyridazine derivatives in preparation of fungicides
  • Application of 3,6-disubstituted imidazo[1, 2-b] pyridazine derivatives in preparation of fungicides
  • Application of 3,6-disubstituted imidazo[1, 2-b] pyridazine derivatives in preparation of fungicides

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Experimental program
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Effect test

Embodiment 1

[0031] A preparation method of 6-chloro-3-phenylimidazo[1,2-b]pyridazine, comprising the steps of:

[0032] (1) Preparation of 6-chloroimidazo[1,2-b]pyridazine:

[0033] 3-amino-6-chloropyridazine (3g, 23mmol) and n-butanol (30mL) were added in a 100mL round bottom flask, and chloroacetaldehyde (4.6mL, 50% aqueous solution) was added dropwise at room temperature and then refluxed for 16 hours. After the reaction is complete, the reaction solution is cooled to room temperature, and n-butanol is evaporated under reduced pressure, then 30 mL of water is added, and NaHCO 3 The solution was adjusted to pH 7, extracted with ethyl acetate (3×50 mL), anhydrous Na 2 SO 4 After drying, the organic phase was concentrated and purified by column chromatography to obtain 3.1 g of white solid compound 6-chloroimidazo[1,2-b]pyridazine (2), with a yield of 90%, M.p.115-117°C; 1 H NMR (400MHz, CDCl 3 ):δ7.35(d,1H,J=9.6Hz),7.85(s,1H),8.22(d,1H,J=9.6Hz),8.34(s,1H). 13 C NMR (100MHz, CDCl 3 ):...

Embodiment 2

[0040] The preparation method of 6-chloro-3-(2,3-dichlorophenyl)imidazo[1,2-b]pyridazine comprises the following steps:

[0041] The preparation steps (1) and (2) of Example 1 are the same, except that the phenylboronic acid in the step (3) of Example 1 is replaced by 2,3-dichlorophenylboronic acid to obtain compound 6 -Chloro-3-(2,3-dichlorophenyl)imidazo[1,2-b]pyridazine (4b), 48% yield, white solid, M.p.194-195℃, 1 H NMR (600MHz, CDCl 3 )δ7.99-7.98 (m, 2H), 7.59 (dd, 1H, J = 8.4Hz, 1.8Hz), 7.54 (dd, 1H, J = 8.4Hz, 1.2Hz), 7.36 (t, 1H, J = 7.8Hz), 7.13(d,1H,J=8.4Hz); 13 C NMR (150MHz, CDCl 3 )δ138.0, 135.5, 134.0, 132.9, 131.1, 130.1, 128.8, 127.3, 127.2, 126.4, 119.1. HRMS (ESI) calcd for C 12 h 7 N 3 Cl 3 [M+H] + m / z: 297.9706, found 297.9712.

Embodiment 3

[0043] The preparation method of 6-chloro-3-(2-fluorophenyl) imidazo[1,2-b]pyridazine comprises the following steps:

[0044] It is the same as the preparation step (1) and step (2) of Example 1, except that the phenylboronic acid in the step (3) of Example 1 is replaced by 2-fluorophenylboronic acid to obtain the compound 6-chloro- 3-(2-Fluorophenyl)imidazo[1,2-b]pyridazine (4c), 77% yield, white solid, M.p.70-72℃, 1 H NMR (400MHz, CDCl 3 )δ8.21(td, 1H, J=7.6Hz, 2.4Hz), 8.15(d, 1H, J=2.8Hz), 8.00(d, 1H, J=9.2Hz), 7.41-7.38(m, 1H) ,7.33-7.30(m,1H),7.24-7.22(m,1H),7.13(d,1H,J=9.6Hz); 13 C NMR (100MHz, CDCl 3 )δ159.8, 157.3, 145.7, 134.8, 134.7, 128.9, 128.1, 126.1, 123.1, 117.5, 115.0, 114.8. HRMS (ESI) calcd for C 12 h 8 N 3 FCl[M+H] + m / z: 248.0391, found 248.0400.

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Abstract

The invention belongs to the technical field of farm chemicals, and specifically relates to application of 3,6-disubstituted imidazo[1, 2-b] pyridazine derivatives in preparation of fungicides. The 3,6-disubstituted imidazo[1, 2-b] pyridazine derivatives are prepared and applied in farm chemical preparation. The inhibition activity of the derivatives on nine common plant pathogenic fungi is testedby adopting a hypha growth rate inhibition method; some of the derivatives show excellent fungistat activity, and are expected to be used for preventing and treating plant diseases caused by pathogenic fungi such as wheat scab, rice blast, cotton blight, tobacco brown spot, cabbage black spot, pumpkin blight, apple ring spot, Curvularia lunata(Walk) Boed and potato dry rot.

Description

technical field [0001] The invention belongs to the technical field of pesticides, in particular to the application of 3,6-disubstituted imidazo[1,2-b]pyridazine derivatives in the preparation of fungicides. Background technique [0002] Crop diseases caused by phytopathogenic fungi are a serious problem in agricultural production worldwide, and phytopathogenic fungi often quickly infect many crops, resulting in reduced food production. In particular, many plant pathogenic fungi, once they enter the food chain, will produce mycotoxins that are harmful to animal and human health [Brase S, Encinas A, Keck J, Nising CF, Chem.Rev.2009, 109, 3903-3990], so In recent years, various pesticide companies have developed and developed a variety of broad-spectrum and high-activity fungicides, which play an important role in ensuring agricultural production and food safety. However, with the abuse of fungicides, it also leads to the cross-resistance of plant pathogenic fungi to fungicid...

Claims

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Application Information

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IPC IPC(8): A01N43/90A01P3/00
CPCA01N43/90
Inventor 樊玲玲李永汤磊罗忠福赵菊琴
Owner GUIZHOU MEDICAL UNIV
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