CN106234385A - A kind of 1,2,4 triazole derivatives containing benzopyrazines structure are as the application of antibacterial - Google Patents

A kind of 1,2,4 triazole derivatives containing benzopyrazines structure are as the application of antibacterial Download PDF

Info

Publication number
CN106234385A
CN106234385A CN201610608888.6A CN201610608888A CN106234385A CN 106234385 A CN106234385 A CN 106234385A CN 201610608888 A CN201610608888 A CN 201610608888A CN 106234385 A CN106234385 A CN 106234385A
Authority
CN
China
Prior art keywords
phenyl
triazole
quinoxaline
compound
application
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201610608888.6A
Other languages
Chinese (zh)
Other versions
CN106234385B (en
Inventor
沈钟华
孙召慧
汪乔
谭成侠
刘幸海
刘旭锋
张永刚
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhejiang University of Technology ZJUT
Original Assignee
Zhejiang University of Technology ZJUT
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zhejiang University of Technology ZJUT filed Critical Zhejiang University of Technology ZJUT
Priority to CN201610608888.6A priority Critical patent/CN106234385B/en
Publication of CN106234385A publication Critical patent/CN106234385A/en
Application granted granted Critical
Publication of CN106234385B publication Critical patent/CN106234385B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention discloses the application as antibacterial of a kind of 1,2,4 triazole derivatives containing benzopyrazines structure.It generates compound (II) with ortho-nitraniline with hydrazine hydrate.React with MBF again, obtain product (III).Compound (III) is used POCl3Chlorination obtains product (IV).Compound thing (IV) and hydrazine hydrate react to obtain intermediate product (V).Compound (V) is with POCl3Make solvent, react to obtain 1,2,4 triazole derivatives containing benzopyrazines structure shown in formula (I) with replacing acid compounds；Its raw material is simple and easy to get, preparation method is simple, convenient post-treatment, and product yield is high, and this compound is for having bactericidal activity, the particularly preventing and treating of fungus point spore anthrax bacteria, Strawberry anthracnose bacterium and Fructus Lycii anthrax bacteria etc. has good effect, and the research and development for novel pesticide provide the foundation.

Description

A kind of 1,2,4-triazole derivative containing benzopyrazines structure is as the application of antibacterial
Technical field
The invention belongs to 1,2,4-triazole class compounds preparing technical fields, it is specifically related to a kind of containing benzopyrazines structure 1,2,4-triazole derivative is as the application of antibacterial.
Background technology
Quinoxaline, the synthesis of triazole compound are chemistry of pesticide, iatrochemistry, polymer chemistry, Coordinative Chemistry Important directions.Quinoxaline compound has significant biological activity, is widely used in the fields such as pesticide, medicine, dyestuff.Three Nitrogen azole compounds is applied at pesticide field because of its good sterilization, weeding, parasite killing and plant growth regulating activity again.Some reports Road display fused heterocyclic compound is generally of the mixed attributes of single heterocycle.In order to find high-efficiency activated noval chemical compound, at benzo Splicing triazole structure in pyrazine structure, synthesis has novel 1,2, the 4-triazole derivatives of bactericidal activity.
The invention provides the preparation of a kind of 1,2,4-triazole derivative containing benzopyrazines structure with bactericidal activity Method and application technology.
Summary of the invention
It is an object of the present invention to provide a kind of 1,2,4-triazole derivative containing benzopyrazines structure with bactericidal activity and Its preparation method and application.
Described a kind of 1,2,4-triazole derivatives containing benzopyrazines structure are as the application of antibacterial, it is characterised in that Its structural formula is as shown in (I):
Wherein: R1For phenyl, 4-n-pro-pyl phenyl, 4-aminomethyl phenyl, 2,4-Dichlorobenzene base, 2-chloropyridine, 4-hydroxy benzenes Base, undecyl, methylamino, 3-pyridine, 4-nitrobenzophenone, 4-tert-butyl-phenyl, 4-methoxyphenyl, 4-aminophenyl, 2- Furan, 2-pyridine.
The described 1,2,4-triazole derivative containing benzopyrazines structure is as preventing and treating fungus point spore anthrax, Fructus Fragariae Ananssae anthrax The application of the antibacterial of bacterium Fructus Lycii anthrax bacteria.
Described application, it is characterised in that 1-(4-methylphenethyl)-4-phenyl-[1,2,4] triazole [4,3-a] quinoline Quinoline, 4-phenyl-1-p-methylphenyl-[1,2,4] triazole [4,3-a] quinoxaline are to fungus point spore anthrax bacteria, Strawberry anthracnose bacterium Good activity is all had with Fructus Lycii anthrax bacteria.
Described application, it is characterised in that 1-(2,4-Dichlorobenzene base)-4-phenyl-[1,2,4] triazole [4,3-a] quinoline Quinoline, 4-(4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline-1-base) phenol, 4-phenyl-1-undecyl-[1,2,4] triazole [4,3-a] quinoxaline, (4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline-1-base) methylamine, 1-(4-(tert-butyl group) phenyl)- 4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline is to fungus point spore anthrax bacteria, Strawberry anthracnose bacterium and Fructus Lycii anthrax bacteria Active.
The preparation method of described 1,2, the 4-triazole derivatives containing benzopyrazines structure, it is characterised in that include walking as follows Rapid:
1) being solvent at methanol, Raney Ni is under catalysts conditions, and ortho-nitraniline and hydrazine hydrate are heated to reflux preparing Compound (II) as shown in formula II；
2) by step 1) compound (II) that obtains and methyl benzoylformate be synthesized the chemical combination as shown in formula III Thing (III) crude product；
3) by step 2) compound (III) crude product that obtains through washing with alcohol after purification, uses POCl3Make solvent, heat back Carrying out chlorination reaction under the conditions of stream, post processing obtains the compound (IV) as shown in formula IV；
4) with ethanol as solvent, by step 3) compound (IV) and the hydrazine hydrate that obtain react the change shown in acquisition formula (V) Compound (V) crude product；
5) by step 4) compound (V) crude product that obtains is after recrystallization purifying, with POCl3Make solvent, with replacing acid Compounds reacts to obtain the 1,2,4-triazole derivative containing benzopyrazines structure shown in formula (I)；
Its preparation process is as follows:
The preparation method of described 1,2, the 4-triazole derivatives containing benzopyrazines structure, it is characterised in that step 1) in, The inventory of each material added is: 0.1mol ortho-nitraniline, 30-50mL methanol, 70-80mL hydrazine hydrate (85%), 0.25 ～0.45g Raney Ni, preferably 0.1mol ortho-nitraniline, 40mL methanol, 75mL hydrazine hydrate (85%), 0.25～0.45g Raney Ni, Raney Ni is weight in wet base.
The preparation method of described 1,2, the 4-triazole derivatives containing benzopyrazines structure, it is characterised in that step 2) in, Compound (II) be firstly dissolved in alcohol, and the volumetric usage of ethanol is calculated as 0.8～1.2ml/mmol with the amount of compound (II) material, Reaction temperature is room temperature, and the response time is 30-90min.
The preparation method of described 1,2, the 4-triazole derivatives containing benzopyrazines structure, it is characterised in that step 3) in after Processing procedure is: be poured slowly in frozen water by reactant liquor, separates out a large amount of yellow solid, and sucking filtration, washing are dried to obtain compound (Ⅳ)。
The preparation method of described 1,2, the 4-triazole derivatives containing benzopyrazines structure, it is characterised in that step 4) in, Compound (IV) is 1:2-4 with the molar ratio of the hydrazine hydrate of 85%.
The preparation method of described 1,2, the 4-triazole derivatives containing benzopyrazines structure, it is characterised in that compound (V) It is 1:1-1.2 with the ratio of the amount of the material of replacing acid compounds, is heated to reflux 3.5-4.5h, preferably 4h.
The preparation method of described 1,2, the 4-triazole derivatives containing benzopyrazines structure, it is characterised in that step 3) in, When carrying out TLC monitoring, extract reaction solution to join and frozen water cracks POCl3, then be extracted with ethyl acetate product, take organic layer, with Ethyl acetate: petroleum ether=1:3 mixed liquor is developing solvent, what monitoring was reacted carries out degree.
Compared with prior art, the beneficial effects are mainly as follows: the invention provides a kind of containing benzopyrazines The 1 of structure, 2,4-triazole derivatives are as the application of antibacterial, and its raw material is simple and easy to get, and preparation method is simple, post processing side Just, product yield is high, and this compound is for having bactericidal activity, especially for preventing and treating fungus point spore anthrax, Fructus Fragariae Ananssae charcoal Cellulitis bacterium, Fructus Lycii anthrax bacteria etc. has good effect, and the research and development for novel pesticide provide the foundation.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in This:
The 1,2,4-triazole derivative (I) containing benzopyrazines structure of the present invention can synthesize in the following manner:
In 250mL single port flask, be sequentially added into 0.1mol ortho-nitraniline, 40mL methanol, 75mL hydrazine hydrate (85%), 0.25～0.45g Raney Ni (weight in wet base), is heated to reflux, and follows the trail of with TLC and disappears to raw material, and reaction is cooled to room temperature after terminating, Being filtered to remove RaneyNi, decompression is distilled off solvent and obtains filbert crystal, obtains the o-phenylenediamine shown in formula II.0.1mol O-phenylenediamine (II), use 100mL ethanol are dissolved, then are slowly added dropwise MBF, and response time section is 30-90min at normal temperatures, After reaction completely, it is filtered to remove solvent, obtains product (III) three times with alcohol flushing.Compound (III) is joined 100mL single port In flask, and use 40mL POCl3Doing and carry out chlorination under solvent, heated reflux condition, reaction is cooled to room temperature, slowly after terminating Pouring in 500g frozen water, separate out a large amount of yellow solid immediately, sucking filtration, washing are dried, and obtain product (IV).Do molten with 60mL ethanol Agent, is slowly added dropwise the hydrazine hydrate of 18g (0.3mol) 85% in product (IV), is warming up to backflow after dropping, reacts 4-5h, Reaction is cooled to room temperature after terminating, and pours in 300g frozen water, separates out a large amount of white solid immediately, through sucking filtration, washs and be dried, system Obtain thick product, obtain intermediate product (V) by recrystallization.By compound (V) with POCl3Make solvent, with replacing acid compounds React to obtain the 1,2,4-triazole derivative containing benzopyrazines structure shown in formula (I).
Embodiment 1～16, the acids synthesis compound 1～16 different from substituent group is as follows, other synthesis condition Do not change.
Embodiment 1
Isosorbide-5-Nitrae-diphenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 71.8%, fusing point 200-203 DEG C；1H NMR (400MHZ, CDCl3/TMS), δ 7.37 (t, J=8.2Hz, 1H, Ph-H), 7.55 (d, J=8.4Hz, 1H, Ph-H), 7.63 (m, 5H, Ph-H), 7.68 (d, J=7.5Hz, 2H, Ph-H), 7.73 (q, J=7.4Hz, 1H, Ph-H), 7.78 (d, J=7.0Hz, 2H, Ph-H), 8.22 (d, J=8.0Hz, 1H, Ph-H), 8.90 (m, 2H, Ph-H) .HRMS (ESI) m/z:Calculated, 323.1291,Found,323.1240[M+H]+.
Embodiment 2
1-(4-methylphenethyl)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 23.6%, fusing point 92-95 ℃；1H NMR (400MHZ, CDCl3/TMS), δ 1.06 (t, J=7.3Hz, 3H, CH3), 1.81 (m, J=7.5Hz, 2H, CH2), 2.79 (t, J=7.7Hz, 2H, CH2), 7.36 (t, J=8.2Hz, 2H, Ph-H), 7.47 (d, J=7.9Hz, 2H, Ph-H), 7.6 (t, J=6.8Hz, 4H, Ph-H), 7.67 (d, J=8.0Hz, 2H, Ph-H), 7.90 (m, 1H, Ph-H), 8.21 (d, J= 8.4Hz,1H,Ph-H),8.90(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,365.1761,Found, 365.1776[M+H]+.
Embodiment 3
4-phenyl-1-p-methylphenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 55.6%, fusing point 90-93 DEG C；1H NMR (400MHZ, CDCl3/TMS), δ 2.45 (s, 3H, CH3), 7.35 (t, J=7.0Hz, 2H, Ph-H), 7.65 (m, 7H, Ph- H),7.93(m,2H,Ph-H),8.21(m,2H,Ph-H),8.88(m,1H,Ph-H).HRMS(ESI)m/z:Calculated, 337.1448,Found,337.1448[M+H]+.
Embodiment 4
1-(2,4-Dichlorobenzene base)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 34.2%, fusing point 113- 117℃；1H NMR (400MHZ, CDCl3/TMS), δ 7.33 (t, J=8.6Hz, 1H, Ph-H), 7.47 (m, 1H, Ph-H), 7.60 (m,2H,Ph-H),7.64(m,1H,Ph-H),7.72(m,1H,Ph-H),7.83(m,1H,Ph-H),7.89(m,1H,Ph-H), 7.96 (d, J=8.5Hz, 1H, Ph-H), 8.10 (m, 1H, Ph-H), 8.25 (d, J=7.2Hz, 1H, Ph-H), 8.92 (m, 1H, Ph-H).HRMS(ESI)m/z:Calculated,391.0512,Found,391.0522[M+H]+.
Embodiment 5
1-(2-chloropyridine-4-base)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 45.5%, fusing point 198- 200℃；1H NMR(400MHZ,CDCl3/TMS),δ7.30(s,1H,Ph-H),7.45(m,1H,Ph-H),7.60-7.68(m, 5H,4Ph-H,1Py-H),8.15(m,1H,Ph-H),8.27(m,1H,Py-H),8.79(m,1H,Py-H),8.91(m,2H,Ph- H).HRMS(ESI)m/z:Calculated,358.0980,Found,358.0854[M+H]+.
Embodiment 6
4-(4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline-1-base) phenol, yield 49.0%, fusing point 143-147 ℃；1H NMR(400MHZ,CDCl3/TMS),δ7.57(m,4H,Ph-H),7.83(m,3H,Ph-H),7.89(m,3H,Ph-H), 8.10(m,2H,Ph-H),8.20(m,1H,Ph-H).HRMS(ESI)m/z:Calculated,358.0980,Found, 358.0868[M+H]+. embodiment 7
4-phenyl-1-undecyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 72.5%, fusing point 93-96 DEG C；1H NMR (400MHZ, CDCl3/TMS), δ 0.90 (t, J=7.0Hz, 3H, CH3), 1.28-1.37 (m, 15H, CH2), 1.45 (m, J =7.4Hz, 1H, CH2), 1.63 (m, J=7.2Hz, 2H, CH2), 2.12 (m, J=7.6Hz, 1H, CH2), 2.37 (t, J= 7.5Hz, 1H, CH2), 3.56 (t, J=7.5Hz, 1H, CH2), 7.60 (m, 3H, Ph-H), 7.70 (m, 1H, Ph-H), 7.83 (m, 1H,Ph-H),7.90(m,1H,Ph-H),8.09-8.26(m,2H,Ph-H),8.85(m,1H,Ph-H).HRMS(ESI)m/z: Calculated,401.2700,Found,401.2699[M+H]+.
Embodiment 8
(4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline-1-base) methylamine, yield 37.2%, fusing point 153-155 DEG C；1H NMR (400MHZ, CDCl3/TMS), δ 7.47 (t, J=6.4Hz, 1H, Ph-H), 7.57 (q, J=4.8Hz, 5H, ph-H), 7.65 (t, J=6.4Hz, 1H, ph-H), 7.75 (t, J=6.0Hz, 3H, ph-H), 7.82 (d, J=6.8Hz, 1H, ph-H), 8.00 (d, J=6.4Hz, 1H, ph-H) .HRMS (ESI) m/z:Calculated, 276.1244, Found, 276.1249 [M+H ]+.
Embodiment 9
4-phenyl-1-(pyridin-3-yl)-[1,2,4] triazole [4,3-a] quinoxaline, yield 62.0%, fusing point 184-187 ℃；1H NMR(400MHZ,CDCl3/TMS),δ7.48(m,3H,Ph-H),7.66-7.73(m,5H,4Ph-H,1Py-H),8.32 (m,1H,Py-H),8.90(m,2H,Ph-H),9.06(m,1H,Ph-H),9.19(m,1H,Py-H).FTIRυ(cm-1): 705.63 1199.43,1570.76,3343.48.
Embodiment 10
1-(4-nitrobenzophenone)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 70.1%, fusing point 162-165 ℃；1H NMR (400MHZ, CDCl3/TMS), δ 7.43 (t, J=6.0Hz, 1H, Ph-H), 7.53 (d, J=6.4Hz, 1H, Ph- H), 7.66 (m, 3H, Ph-H), 8.05 (d, J=6.8Hz, 2H, Ph-H), 8.28 (d, J=5.2Hz, 1H, Ph-H), 8.35 (d, J =6.8Hz, 1H, Ph-H), 6.55 (d, J=6.8Hz, 2H, Ph-H), 8.89 (m, 2H, Ph-H).
Embodiment 11
1-(4-(tert-butyl group) phenyl)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 43.9%, fusing point 152-155℃；1H NMR (400MHZ, CDCl3/TMS), δ 1.38 (s, 9H, CH3), 7.41 (t, J=7.5Hz, 1H, Ph-H), 7.52 (d, J=8.4Hz, 2H, Ph-H), 7.61-7.72 (m, 6H, Ph-H), 8.06 (d, J=8.4Hz, 2H, Ph-H), 8.23 (d, J=8.05Hz, 1H, Ph-H), 8.90 (m, 1H, Ph-H).
Embodiment 12
1-(4-anisyl)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 18.2%, fusing point 182-184 ℃；1H NMR (400MHZ, CDCl3/TMS), δ 3.98 (s, 3H, OCH3), 7.17 (d, J=8.4Hz, 2H, Ph-H), 7.39 (t, J=7.8Hz, 1H, Ph-H), 7.62 (m, 5H, Ph-H), 7.69 (d, J=8.4Hz, 2H, Ph-H), 8.21 (d, J=7.9Hz, 1H,Ph-H),8.89(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,353.1397,Found,353.1399[M+H ]+.
Embodiment 13
4-(4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline-1-base) aniline, yield 87.0%, fusing point 187-190 ℃；1H NMR (400MHZ, CDCl3/TMS), δ 6.91 (d, J=6.8Hz, 2H, Ph-H), 7.40 (t, J=6.0Hz, 1H, Ph- H), 7.52 (m, 3H, Ph-H), 7.63 (m, 4H, 2Ph-H, 2NH), 7.77 (d, J=6.8Hz, 1H, Ph-H), 8.12 (d, J= 6.4Hz, 1H, Ph-H), 8.21 (d, J=6.4Hz, 1H, Ph-H), 8.89 (m, 2H, Ph-H) .HRMS (ESI) m/z: Calculated,338.1400,Found,338.1403[M+H]+.
Embodiment 14
1-(furan-2-base)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 63.5%, fusing point 201-204 ℃；1H NMR (400MHZ, CDCl3/TMS), δ 6.80 (m, 1H, furan-H), 7.18 (d, J=3.2Hz, 1H, furan-H), 7.46 (d, J=8,4Hz, 1H, Ph-H), 7.55 (t, J=7.2Hz, 1H, Ph-H), 7.63-7.69 (m, 5H, Ph-H), 7.84 (m, 1H, Ph-H), 8.24 (d, J=8.0,1H, furan-H), 8.89 (m, 2H, Ph-H) .HRMS (ESI) m/z: Calculated,313.1084,Found,313.1082[M+H]+.
Embodiment 15
4-phenyl-1-(pyridine-2-base)-[1,2,4] triazole [4,3-a] quinoxaline, yield 19.1%, fusing point 199-202 ℃；1H NMR(400MHZ,CDCl3/TMS),δ7.50(m,2H,Ph-H),7.59-7.69(m,5H,Ph-H),7.83(m,2H, Ph-H), 8.13 (d, J=7.6Hz, 1H, Py-H), 8.26 (d, J=8.0Hz, 1H, Py-H), 8.90 (m, 2H, Py-H) .HRMS (ESI)m/z:Calculated,346.1063,324.1244,Found,346.1088[M+Na]+,324.1271[M+H]+.
Embodiment 16
1-(3-fluorophenyl)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 51.2%, fusing point 197-200 ℃；1H NMR (400MHZ, CDCl3/TMS), δ 7.43 (m, 2H, Ph-H), 7.52 (d, J=8.4Hz, 1H, Ph-H), 7.57 (d, J=8.8Hz, 2H, Ph-H), 7.65 (m, 5H, Ph-H), 6.24 (d, J=8.0Hz, 1H, Ph-H), 8.89 (m, 2H, Ph-H) .HRMS(ESI)m/z:Calculated,363.1016,341.1197,Found,300.0[M+H]+,363.1043[M+Na]+, 341.1489[M+H]+.
Embodiment 17 bactericidal activity is tested
Subjects: fungus point spore anthrax, Fructus Fragariae Ananssae anthrax, Fructus Lycii anthrax bacteria.
Test method: the preparation of pathogen and preservation: test fungus point spore anthrax (Colletrotichum anthrax CaGoff), Fructus Fragariae Ananssae anthrax (Colletrotichum fragariae Cf63), Fructus Lycii anthrax bacteria (Colletrotichum Gloeosporioides Cg162) it is stored in natural product research on utilization institute of agricultural research institute of the Ministry of Agriculture of United States Department of Agriculture (USDA) (USDA-ARS, Natural Products Utilization Research Unit) David Wedge seminar.Three kinds of charcoals Cellulitis strain all isolateds from Fructus Fragariae Ananssae.
Inoculation method: the conidium of each fungal species is brushed lamellae gently with a L-shaped Glass rod.
Directly bioautography: after waiting test to terminate, measures the radius size of thin layer chromatography version.
Compound 1-16 is to fungus point spore anthrax, Fructus Fragariae Ananssae anthrax, the room of 3 antibacterial targets such as Fructus Lycii anthrax bacteria Interior Vivo Studies on Screening the results are shown in Table 1.
The bactericidal activity data of table 1 compound 1-16
Knowable to above-mentioned table 1, compound sets under concentration the bactericidal activity testing selected 3 kinds of targets in test.Chemical combination Fungus point spore anthrax bacteria, Strawberry anthracnose bacterium and Fructus Lycii anthrax bacteria are all had good under the conditions of microtitration by thing 2,3 Activity, 4,6,7,8,11 pairs of fungus point spore anthrax bacterias of compound, Strawberry anthracnose bacterium and Fructus Lycii anthrax bacteria have certain activity.

Claims (4)

1. 1,2, the 4-triazole derivatives application as antibacterial containing benzopyrazines structure, it is characterised in that its structural formula As shown in (I):
Wherein: R1For phenyl, 4-n-pro-pyl phenyl, 4-aminomethyl phenyl, 2,4-Dichlorobenzene base, 2-chloropyridine, 4-hydroxy phenyl, ten One alkyl, methylamino, 3-pyridine, 4-nitrobenzophenone, 4-tert-butyl-phenyl, 4-methoxyphenyl, 4-aminophenyl, 2-furan, 2-pyridine.
1,2,4-triazole derivative containing benzopyrazines structure the most according to claim 1 is as preventing and treating fungus point spore anthrax Bacterium, the application of antibacterial of Fructus Fragariae Ananssae anthrax Fructus Lycii anthrax bacteria.
Application the most according to claim 1 and 2, it is characterised in that 1-(4-methylphenethyl)-4-phenyl-[1,2,4] three Azoles [4,3-a] quinoxaline, 4-phenyl-1-p-methylphenyl-[1,2,4] triazole [4,3-a] quinoxaline to fungus point spore anthrax bacteria, Strawberry anthracnose bacterium and Fructus Lycii anthrax bacteria all have good activity.
Application the most according to claim 1 and 2, it is characterised in that 1-(2,4-Dichlorobenzene base)-4-phenyl-[1,2,4] three Azoles [4,3-a] quinoxaline, 4-(4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline-1-base) phenol, 4-phenyl-1-hendecane Base-[1,2,4] triazole [4,3-a] quinoxaline, (4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline-1-base) methylamine, 1-(4- (tert-butyl group) phenyl)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline is to fungus point spore anthrax bacteria, Strawberry anthracnose bacterium Active with Fructus Lycii anthrax bacteria.
CN201610608888.6A 2016-07-28 2016-07-28 A kind of application of 1,2,4- triazole derivatives of the structure containing benzopyrazines as fungicide Active CN106234385B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610608888.6A CN106234385B (en) 2016-07-28 2016-07-28 A kind of application of 1,2,4- triazole derivatives of the structure containing benzopyrazines as fungicide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610608888.6A CN106234385B (en) 2016-07-28 2016-07-28 A kind of application of 1,2,4- triazole derivatives of the structure containing benzopyrazines as fungicide

Publications (2)

Publication Number Publication Date
CN106234385A true CN106234385A (en) 2016-12-21
CN106234385B CN106234385B (en) 2018-11-13

Family

ID=57604560

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610608888.6A Active CN106234385B (en) 2016-07-28 2016-07-28 A kind of application of 1,2,4- triazole derivatives of the structure containing benzopyrazines as fungicide

Country Status (1)

Country Link
CN (1) CN106234385B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112745318A (en) * 2019-10-29 2021-05-04 北京鼎材科技有限公司 Compound and application thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101016300A (en) * 2007-02-14 2007-08-15 浙江工业大学 Triazole pyrimidine sulphonates compound, preparing method and application thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101016300A (en) * 2007-02-14 2007-08-15 浙江工业大学 Triazole pyrimidine sulphonates compound, preparing method and application thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
EAKTA ET AL.: "A reinvestigation of reaction of 2-hydrazino-3-phenylquinoxaline with 1,3-diketones: synthesis and characterization of regioisomeric 1-(3’-phenylquinoxalin-2’-yl)-3,5-disubstituted pyrazoles and 1,2,4-triazolo[4,3-a]quinoxalines", 《INDIAN JOURNAL OF CHEMISTRY》 *
王献友等: "1，2，4-三唑类化合物杀菌活性的研究进展", 《江苏农业科学》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112745318A (en) * 2019-10-29 2021-05-04 北京鼎材科技有限公司 Compound and application thereof
CN112745318B (en) * 2019-10-29 2024-03-19 北京鼎材科技有限公司 Compound and application thereof

Also Published As

Publication number Publication date
CN106234385B (en) 2018-11-13

Similar Documents

Publication Publication Date Title
CN103467380B (en) Substituted phenyl pyrazole amide derivative and preparation method and application thereof
EP3632905B1 (en) Method for preparing n-acyl ortho-aminobenzamide
CN109090123A (en) Application of the new cryptolepine derivative in prevention and treatment plant source germ
CN103641827A (en) Purrocoline derivative and synthetic method and application thereof
KR101827660B1 (en) Fluorophenyl pyrazol compounds
CN113135856B (en) 3-trifluoromethyl-5-cyanopyrazole compounds and preparation method thereof
CN104892602B (en) The hydazone derivative of a kind of 1,2,4-triazole [4,3-a] pyridine ring and preparation and application thereof
CN106188011B (en) The ultrasound synthesis and application of quaternary ring-type beta-lactam derivatives based on arylpyrazole skeleton
CN106234385A (en) A kind of 1,2,4 triazole derivatives containing benzopyrazines structure are as the application of antibacterial
CN109705101B (en) Pyrazole triazole sulfonamide compound and solvothermal synthesis method and application thereof
CN109422734B (en) Nortopstein alkaloid derivative, preparation thereof and application thereof in pest control
CN106432245B (en) A kind of 1,2,4- triazole derivatives of the structure containing benzopyrazines and its preparation method and application
CN104610267B (en) Method for efficiently synthesizing 6-alkyl pyrazolo [1,5-c ] quinazoline framework compound under non-catalytic condition
CN108250156B (en) Cinnamylate oxadiazine derivative and preparation method and application thereof
CN113072481B (en) Indolo-cyclobutane skeleton compound, synthesis method and application
CN106234387B (en) A kind of application of the 1,2,4- triazole derivative of the structure of benzopyrazines containing methyl as fungicide
CN106220633A (en) 1,2,4 triazole derivatives of a kind of chloride benzopyrazines structure are as the application of antibacterial
CN105272918B (en) Halogenation -1- alkyl -3- vinyl -2,4,5- triarylimidazoles and preparation method and purposes
CN104059062A (en) Benzothiazole and triazolediheterocycle-containing fused ring compound and application thereof
CN109369528B (en) Trifluoromethyl substituted cyclopentanone quinoline compound, pharmaceutically acceptable salt, preparation method and application thereof
CN106243109B (en) A kind of 1,2,4- triazole derivatives of the structure of benzopyrazines containing methyl and its preparation method and application
CN110483405B (en) Kealiinine derivatives, preparation thereof and application thereof in resisting plant viruses and germs
CN106336415B (en) A kind of 1,2,4- triazole derivatives of chloride benzopyrazines structure and its preparation method and application
CN114957215B (en) Methylene bridged quinoline and 1,2, 3-triazole diheterocyclic compound and preparation method and application thereof
CN106243110B (en) A kind of 1,2,4- triazole derivatives of the structure of benzopyrazines containing methoxyl group and its preparation method and application

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
EE01 Entry into force of recordation of patent licensing contract
EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20161221

Assignee: Hangzhou baibeiyou Biotechnology Co.,Ltd.

Assignor: JIANG University OF TECHNOLOGY

Contract record no.: X2023980033594

Denomination of invention: Application of a 1,2,4-triazole derivative containing benzopyrazine structure as a fungicide

Granted publication date: 20181113

License type: Common License

Record date: 20230315

Application publication date: 20161221

Assignee: Hangzhou Guangyoujiu Enterprise Management Partnership (L.P.)

Assignor: JIANG University OF TECHNOLOGY

Contract record no.: X2023980033595

Denomination of invention: Application of a 1,2,4-triazole derivative containing benzopyrazine structure as a fungicide

Granted publication date: 20181113

License type: Common License

Record date: 20230316

Application publication date: 20161221

Assignee: Hangzhou Zhiguo Enterprise Service Co.,Ltd.

Assignor: JIANG University OF TECHNOLOGY

Contract record no.: X2023980033596

Denomination of invention: Application of a 1,2,4-triazole derivative containing benzopyrazine structure as a fungicide

Granted publication date: 20181113

License type: Common License

Record date: 20230316

EE01 Entry into force of recordation of patent licensing contract
EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20161221

Assignee: Deqing Wucheng Agricultural Development Co.,Ltd.

Assignor: JIANG University OF TECHNOLOGY

Contract record no.: X2023980040519

Denomination of invention: Application of a 1,2,4-triazole derivative containing benzopyrazine structure as a fungicide

Granted publication date: 20181113

License type: Common License

Record date: 20230828