CN106234387A - A kind of 1,2,4 triazole derivatives containing methyl benzopyrazines structure are as the application of antibacterial - Google Patents
A kind of 1,2,4 triazole derivatives containing methyl benzopyrazines structure are as the application of antibacterial Download PDFInfo
- Publication number
- CN106234387A CN106234387A CN201610613203.7A CN201610613203A CN106234387A CN 106234387 A CN106234387 A CN 106234387A CN 201610613203 A CN201610613203 A CN 201610613203A CN 106234387 A CN106234387 A CN 106234387A
- Authority
- CN
- China
- Prior art keywords
- phenyl
- methyl
- triazole
- compound
- quinoxaline
- 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
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 methyl benzopyrazines structure.It generates compound (II) with 4 methyl ortho-nitranilines 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 methyl 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
Technical field
The invention belongs to 1,2,4-triazole class compounds preparing technical fields, it is specifically related to a kind of containing methyl benzopyrazines knot
The 1,2,4-triazole derivative of structure 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 a kind of 1,2,4-triazole derivative containing methyl benzopyrazines structure with bactericidal activity
Preparation 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 methyl benzopyrazines structure as antibacterial
Application.
Described a kind of 1,2,4-triazole derivatives containing methyl benzopyrazines structure are as the application of antibacterial, its feature
It is that its structural formula is as shown in (I):
Wherein: R1For phenyl, 2-fluorophenyl, undecyl, 3-aminomethyl phenyl, 3-methoxyphenyl, 3-chlorphenyl, 3-nitre
Base phenyl, 2-aminomethyl phenyl, 4-nitrobenzophenone, 4-aminophenyl, 4-tert-butyl-phenyl, 4-fluorophenyl, 4-methoxyphenyl, 2,
4-Dichlorobenzene base, 2-chloropyridine.
The described 1,2,4-triazole derivative containing methyl benzopyrazines structure is as fungus point spore anthrax bacteria, Fructus Fragariae Ananssae charcoal
Cellulitis pathogenic bacteria and the application of Fructus Lycii anthrax bacteria antibacterial.
Described application, it is characterised in that 8-methyl isophthalic acid-(3-nitrobenzophenone)-4-phenyl-[1,2,4] triazole [4,3-a]
Quinoxaline, 8-methyl 4-phenyl-1-o-methyl-phenyl--[1,2,4] triazole [4,3-a] quinoxaline, 8-methyl isophthalic acid-(4-Nitrobenzol
Base)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, 1-(4-tert-butyl-phenyl)-8-methyl 4-phenyl-[1,2,4] three
Azoles [4,3-a] quinoxaline fungus point spore anthrax bacteria, Strawberry anthracnose bacterium and Fructus Lycii anthrax bacteria antibacterial are active.
The preparation method of described a kind of 1,2,4-triazole derivatives containing methyl benzopyrazines structure, it is characterised in that bag
Include following steps:
1) being solvent at methanol, Raney Ni is under catalysts conditions, and 4-methyl-2-nitroaniline and hydrazine hydrate heat back
Stream prepares the 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, TCL monitoring reaction obtains the compound (IV) as shown in formula IV through post processing after terminating, and
Carry out the next step；
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) (7-methyl-3-phenyl quinoxaline-2-base) hydrazine 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 methyl benzopyrazines structure shown in formula (I)；
Its preparation process is as follows:
The preparation method of described 1,2, the 4-triazole derivatives containing methyl benzopyrazines structure, it is characterised in that step 1)
In, the amount of each material of addition is: 0.1mol 4-methyl-2-nitroaniline, 30-50mL methanol, 70-80mL hydrazine hydrate
(85%), 0.25～0.45g Raney Ni, preferably 0.1mol 4-methyl-2-nitroaniline, 40mL methanol, 75mL hydration
Hydrazine (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 methyl benzopyrazines structure, it is characterised in that step 2)
Middle reaction temperature is room temperature, and response time section is 30-90min.
The preparation method of described 1,2, the 4-triazole derivatives containing methyl benzopyrazines structure, it is characterised in that step 3)
Middle post-processing approach is: be poured slowly into after completion of the reaction in frozen water, separates out a large amount of yellow solid, sucking filtration, being dried to obtain of washing
Compound (IV).
The preparation method of described 1,2, the 4-triazole derivatives containing methyl benzopyrazines structure, it is characterised in that step 4)
In, compound (IV) with 85% the molar ratio of hydrazine hydrate be 1:2.8-3.2, preferably molar ratio be 1:3.
The preparation method of described 1,2, the 4-triazole derivatives containing methyl benzopyrazines structure, it is characterised in that compound
(V) ratio with the amount of the material of replacing acid compounds is 1:1-1.2, and the time of being heated to reflux is 3.5-4.5, preferred substance
The ratio of amount is 1:1, and the time of being heated to reflux is 4h.
The preparation method of described 1,2, the 4-triazole derivatives containing methyl benzopyrazines structure, it is characterised in that step 3)
In, when carrying out TLC monitoring, extract reaction solution, join and frozen water cracks POCl3, then it is extracted with ethyl acetate product, take organic
Layer, with ethyl acetate: petroleum ether=1:3 mixed liquor is as developing solvent, and what monitoring was reacted carries out degree.
The described 1,2,4-triazole derivative containing methyl benzopyrazines structure is as the application of herbicide.
The described 1,2,4-triazole derivative containing methyl benzopyrazines structure preventing and treating creeping bentgrass, Caulis et Folium Lactucae Sativae weeds should
With.
Compared with prior art, the beneficial effects are mainly as follows: the invention provides a kind of benzo Han methyl
The 1 of pyrazine structure, preparation method of 2,4-triazole derivatives and its preparation method and application, its raw material is simple and easy to get, preparation side
Method is simple, convenient post-treatment, and product yield is high, and this compound is for having bactericidal activity, especially for preventing and treating fungus point
Spore anthrax, Fructus Fragariae Ananssae anthrax, the preventing and treating of Fructus Lycii anthrax bacteria etc. has good effect, and the research and development for novel pesticide provide base
Plinth.
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 methyl benzopyrazines structure of the present invention can synthesize in the following manner:
In 250mL single port flask, it is sequentially added into 0.1mol 4-methyl-2-nitroaniline, 40mL methanol, 75mL hydration
Hydrazine (85%), 0.25～0.45g Raney Ni (weight in wet base), be heated to reflux, and follows the trail of with TLC and disappears to raw material, and reaction is cold after terminating
But to room temperature, being filtered to remove Raney Ni, decompression is distilled off solvent and obtains filbert crystal, obtains the 4-methyl shown in formula II
O-phenylenediamine.0.1mol 4-methyl-o-phenylenediamine (II), use 100mL ethanol are dissolved, then are slowly added dropwise MBF, at normal temperatures
Response time section is 30-90min, after reaction completely, is filtered to remove solvent, obtains product (III) three times with alcohol flushing.By chemical combination
Thing (III) joins in 100mL single port flask, and uses 40mL POCl3Do and under solvent, heated reflux condition, carry out chlorination, reaction
Being cooled to room temperature after end, be poured slowly in 500g frozen water, separate out a large amount of yellow solid immediately, sucking filtration, washing are dried, and are produced
Thing (IV).Make solvent with 60mL ethanol, product (IV) is slowly added dropwise the hydrazine hydrate of 18g (0.3mol) 85%, drips complete
After be warming up to backflow, react 4-5h, reaction is cooled to room temperature after terminating, pours in 300g frozen water, separates out a large amount of white immediately solid
Body, through sucking filtration, washs and is dried, and prepares thick product, obtains intermediate product (V) by recrystallization.By compound (V) with POCl3
Make solvent, react to obtain 1,2, the 4-triazole derivatives containing methyl benzopyrazines structure shown in formula (I) with replacing acid compounds.
Embodiment 1～15, the acids synthesis compound 1～15 different from substituent group is as follows, other synthesis condition
Do not change.
Embodiment 1
8-methyl isophthalic acid, 4-diphenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 41.8%, fusing point 176-178 DEG C；1H NMR(400MHZ,CDCl3/TMS),δ2.50(s,3H,CH3),6.95(m,1H,Ph-H),7.13(m,1H,Ph-H),
7.32-7.88(m,9H,Ph-H),8.10(s,1H,Ph-H),8.29(s,1H,NH),8.70(m,1H,CH),11.65(m,1H,
OH).HRMS(ESI)m/z:Calculated,337.1448,Found,337.1453[M+H]+.
Embodiment 2
1-(4-fluorophenyl)-8-methyl 4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 55.3%, fusing point
193-196℃；1H NMR (400MHZ, CDCl3/TMS), δ 7.54 (s, 3H, CH3), 7.23 (d, J=8.5Hz, 1H, Ph-H),
7.33(s,1H,Ph-H),7.44(m,3H,Ph-H),7.5(m,1H,Ph-H),7.57(m,1H,Ph-H),8.04(s,1H,Ph-
H), 8.11 (d, J=8.2Hz, 1H, Ph-H), 8.87 (m, 3H, Ph-H) .HRMS (ESI) m/z:Calculated, 355.1354,
Found,355.1363[M+H]+.
Embodiment 3
8-methyl 4-phenyl-1-undecyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 54.5%, fusing point 127-
130℃；1H NMR (400MHZ, CDCl3/TMS), δ 0.90 (t, J=6.5Hz, 3H, CH3), 1.28 (m, 14H, CH2), 1.64
(m, 2H, CH2), 2.10 (m, 2H, CH2), 3.52 (q, J=7.90Hz, 2H, CH2), 7.50 (d, J=7.7Hz, 1H, Ph-H),
7.59(m,3H,Ph-H),7.93-8.12(m,2H,Ph-H),8.83(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,
415.2856,Found,415.2864[M+H]+.
Embodiment 4
Aminomethyl phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 44.3%, fusing point between 8-methyl 4-phenyl-1-
174-177℃；1H NMR(400MHZ,CDCl3/TMS),δ2.45(s,3H,CH3),2.52(s,3H,CH3),7.38(m,2H,
Ph-H), 7.45 (m, 2H, Ph-H), 7.53 (m, 3H, Ph-H), 7.60 (d, J=8.0Hz, 1H, Ph-H), 7.95 (s, 1H, Ph-
H), 8.10 (d, J=8.2Hz, 1H, Ph-H), 8.88 (m, 2H, Ph-H) .HRMS (ESI) m/z:Calculated, 351.1604,
Found,351.1605[M+H]+.
Embodiment 5
1-(3-methoxyphenyl)-8-methyl 4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 58.9%, molten
Point 117-120 DEG C；1H NMR(400MHZ,CDCl3/TMS),δ2.53(s,3H,CH3),3.68(s,3H,OCH3),7.34(d,J
=4.7Hz, 1H, Ph-H), 7.42 (m, 1H, Ph-H), 7.6-7.71 (m, 5H, Ph-H), 8.02 (s, 1H, Ph-H), 8.09 (d, J
=8.2Hz, 1H, Ph-H), 8.88 (m, 3H, Ph-H) .HRMS (ESI) m/z:Calculated, 367.1553, Found,
367.1555[M+H]+.
Embodiment 6
1-(3-chlorphenyl)-8-methyl 4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 64.2%, fusing point
183-185℃；1H NMR (400MHZ, CDCl3/TMS), δ 2.55 (s, 3H, CH3), 7.36 (s, 1H, Ph-H), 7.45 (t, J=
8.3Hz, 3H, Ph-H), 7.80 (m, 1H, Ph-H), 8.09 (s, 1H, Ph-H), 8.12 (d, J=8.2Hz, 1H, Ph-H), 8.86
(m,3H,Ph-H).HRMS(ESI)m/z:Calculated,371.1058,Found,371.1059[M+H]+.
Embodiment 7
8-methyl isophthalic acid-(3-nitrobenzophenone)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 65.1%, fusing point
165-167℃；1H NMR (400MHZ, CDCl3/TMS), δ 2.56 (s, 3H, CH3), 7.24 (m, 1H, Ph-H), 7.38 (d, J=
8.6Hz, 1H, Ph-H), 7.49 (m, 1H, Ph-H), 7.90 (d, J=3.2Hz, 1H, Ph-H), 8.08 (s, 1H, Ph-H), 8.18
(q, J=7.3Hz, 2H, Ph-H), 8.59 (m, 1H, Ph-H), 8.70 (m, 1H, Ph-H), 8.87 (m, 3H, Ph-H) .HRMS
(ESI)m/z:Calculated,382.1299,Found,382.1300[M+H]+.
Embodiment 8
8-methyl 4-phenyl-1-o-methyl-phenyl--[1,2,4] triazole [4,3-a] quinoxaline, yield 52.9%, fusing point
180-183℃；1H NMR(400MHZ,CDCl3/TMS),δ2.29(s,3H,CH3),2.52(s,3H,CH3),7.41(m,1H,
CH3), 7.49 (m, 4H, CH3), 7.57 (d, J=7.4Hz, 2H, Ph-H), 8.02 (s, 1H, Ph-H), 8.09 (d, J=8.2Hz,
1H,Ph-H),8.90(m,3H,Ph-H).HRMS(ESI)m/z:Calculated,351.1604,Found,351.1602[M+H
]+.
Embodiment 9
8-methyl isophthalic acid-(4-nitrobenzophenone)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 29.6%, fusing point
183-185℃；1H NMR(400MHZ,CDCl3/TMS),δ2.54(s,3H,CH3),7.52(m,2H,Ph-H),7.62(m,5H,
Ph-H),8.00(s,1H,Ph-H),8.86(m,3H,Ph-H).HRMS(ESI)m/z:Calculated,382.1299,Found,
382.1749[M+H]+.
Embodiment 10
4-(8-methyl 4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline-1-base)-aniline, yield 27.5%, fusing point
130-133℃；1H NMR(400MHZ,CDCl3/TMS),δ2.54(s,3H,CH3),6.91(m,1H,Ph-H),7.10(m,1H,
Ph-H),7.41-7.61(m,7H,Ph-H),8.02(s,1H,Ph-H),8.86(m,2H,Ph-H).HRMS(ESI)m/z:
Calculated,352.1557,Found,352.1560[M+H]+.
Embodiment 11
1-(4-tert-butyl-phenyl)-8-methyl 4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 47.1%, molten
Point 144-147 DEG C；1H NMR(400MHZ,CDCl3/TMS),δ1.46(s,9H,CH3),2.53(s,3H,CH3),7.52(d,J
=8.3Hz, 3H, Ph-H), 7.63 (m, 2H, Ph-H), 7.68 (m, 2H, Ph-H), 8.06 (d, J=8.2Hz, 3H, Ph-H),
8.87(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,393.2074,Found,393.2078[M+H]+.
Embodiment 12
1-(4-fluorophenyl)-8-methyl 4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 56.0%, fusing point
126-129℃；1H NMR(400MHZ,CDCl3/TMS),δ2.55(m,3H,CH3),7.38(m,2H,Ph-H),7.64(m,3H,
Ph-H),7.19(m,1H,Ph-H),8.07(s,1H,Ph-H),8.14(m,2H,Ph-H),8.87(m,3H,Ph-H).HRMS
(ESI)m/z:Calculated,355.1354,Found,355.1364[M+H]+.
Embodiment 13
1-(4-methoxyphenyl)-8-methyl 4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 54.8%, molten
Point 127-129 DEG C；1H NMR(400MHZ,CDCl3/TMS),δ2.56(s,3H,CH3),3.96(s,3H,Ph-H),7.43(m,
1H, Ph-H), 7.50 (d, J=6.8Hz, 1H, Ph-H), 8.01 (s, 1H, Ph-H), 8.09 (d, J=6.8Hz, 6H, Ph-H),
8.86(m,3H,Ph-H).HRMS(ESI)m/z:Calculated,367.1553,Found,367.1562[M+H]+.
Embodiment 14
1-(2,4-Dichlorobenzene base)-8-methyl 4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 54.8%, molten
Point 127-129 DEG C；1H NMR (400MHZ, CDCl3/TMS), δ 2.55 (m, 3H, CH3), 7.36 (d, J=6.4Hz, 1H, Ph-
H), 7.47 (d, J=6.4Hz, 1H, Ph-H), 7.53 (s, 1H, Ph-H), 7.59 (t, J=5.2Hz, 2H, Ph-H), 7.73 (m,
2H, Ph-H), 7.96 (d, J=6.4Hz, 1H, Ph-H), 8.05 (s, 1H, Ph-H), 8.12 (d, J=6.4Hz, 1H, Ph-H),
8.89(m,3H,Ph-H).HRMS(ESI)m/z:Calculated,405.0688,Found,405.0687[M+H]+.
Embodiment 15
1-(2-chloropyridine-4-base)-8-methyl 4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 38.6%,
Fusing point 186-189 DEG C；1H NMR (400MHZ, CDCl3/TMS), δ 2.56 (m, 3H, CH3), 7.47 (d, J=6.4Hz, 1H, Ph-
H),7.65(m,2H,Ph-H),8.07(s,1H,Ph-H),8.15(m,2H,Py-H),8.79(m,2H,Py-H),8.89(m,3H,
Ph-H).HRMS(ESI)m/z:Calculated,372.1010,Found,372.1023[M+H]+.
Embodiment 16 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 1-15 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 1-15
Knowable to above-mentioned table 1, the sterilization and activation testing selected 3 kinds of targets is closed under test sets concentration by this compounds
7,8,9,11 pairs of fungus point spore anthrax bacterias of thing, Strawberry anthracnose bacterium and Fructus Lycii anthrax bacteria are the most active.
Claims (3)
1. 1,2, the 4-triazole derivatives application as antibacterial containing methyl benzopyrazines structure, it is characterised in that its knot
Structure formula is as shown in (I):
Wherein: R1For phenyl, 2-fluorophenyl, undecyl, 3-aminomethyl phenyl, 3-methoxyphenyl, 3-chlorphenyl, 3-Nitrobenzol
Base, 2-aminomethyl phenyl, 4-nitrobenzophenone, 4-aminophenyl, 4-tert-butyl-phenyl, 4-fluorophenyl, 4-methoxyphenyl, 2,4-bis-
Chlorphenyl, 2-chloropyridine.
1,2,4-triazole derivative containing methyl benzopyrazines structure the most according to claim 1 is as fungus point spore anthrax
Pathogenic bacteria, Strawberry anthracnose bacterium and the application of Fructus Lycii anthrax bacteria antibacterial.
Application the most according to claim 2, it is characterised in that 8-methyl isophthalic acid-(3-nitrobenzophenone)-4-phenyl-[1,2,4]
Triazole [4,3-a] quinoxaline, 8-methyl 4-phenyl-1-o-methyl-phenyl--[1,2,4] triazole [4,3-a] quinoxaline, 8-methyl-
1-(4-nitrobenzophenone)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, 1-(4-tert-butyl-phenyl)-8-methyl-4-benzene
Base-[1,2,4] triazole [4,3-a] quinoxaline fungus point spore anthrax bacteria, Strawberry anthracnose bacterium and Fructus Lycii anthrax bacteria antibacterial
Active.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610613203.7A CN106234387B (en) | 2016-07-28 | 2016-07-28 | A kind of application of the 1,2,4- triazole derivative of the structure of benzopyrazines containing methyl as fungicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610613203.7A CN106234387B (en) | 2016-07-28 | 2016-07-28 | A kind of application of the 1,2,4- triazole derivative of the structure of benzopyrazines containing methyl as fungicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106234387A true CN106234387A (en) | 2016-12-21 |
| CN106234387B CN106234387B (en) | 2019-04-26 |
Family
ID=57605862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610613203.7A Active CN106234387B (en) | 2016-07-28 | 2016-07-28 | A kind of application of the 1,2,4- triazole derivative of the structure of benzopyrazines containing methyl as fungicide |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106234387B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113943260A (en) * | 2020-07-15 | 2022-01-18 | 威智医药有限公司 | Cyclic compound and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013034755A1 (en) * | 2011-09-09 | 2013-03-14 | H. Lundbeck A/S | Triazolopyrazine derivatives and their use for treating neurological and psychiatric disorders |
-
2016
- 2016-07-28 CN CN201610613203.7A patent/CN106234387B/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113943260A (en) * | 2020-07-15 | 2022-01-18 | 威智医药有限公司 | Cyclic compound and preparation method and application thereof |
| CN113943260B (en) * | 2020-07-15 | 2023-10-27 | 威智医药股份有限公司 | Cyclic compound and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106234387B (en) | 2019-04-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103467380B (en) | Substituted phenyl pyrazole amide derivative and preparation method and application thereof | |
| TW200800927A (en) | Chemical compounds | |
| CN108997253B (en) | Mandelic acid derivatives containing 1,3, 4-oxadiazole thioether and application thereof | |
| CN109169668B (en) | Application of 2-aryl substituted pyrrole compound in drug for killing vesicular snails | |
| CN103130769B (en) | 3-difluoro ethoxy-pyrazole amides compounds and application thereof | |
| CN109232429B (en) | Bisamide compound containing 1, 3-dialkyl substituted pyrazole, and preparation method and application thereof | |
| CN102746282A (en) | N-5-substituted phenyl-2-furoyl compounds, preparation method and application thereof | |
| CN106496065A (en) | A kind of o-phenylenediamine Schiff base derivatives and preparation method and application | |
| CN106234387A (en) | A kind of 1,2,4 triazole derivatives containing methyl benzopyrazines structure are as the application of antibacterial | |
| CN109705101B (en) | Pyrazole triazole sulfonamide compound and solvothermal synthesis 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 | |
| CN107459490A (en) | The Carbox amide of azophenlyene 1 and its application | |
| CN101407496B (en) | Method for synthesizing 3,5-disubstituted pyrazole | |
| CN106234385B (en) | A kind of application of 1,2,4- triazole derivatives of the structure containing benzopyrazines as fungicide | |
| CN106432245B (en) | A kind of 1,2,4- triazole derivatives of the structure containing benzopyrazines and its preparation method and application | |
| CN106220633A (en) | 1,2,4 triazole derivatives of a kind of chloride benzopyrazines structure are as the application of antibacterial | |
| CN111393348B (en) | Nitrogen-substituted phenylpyrrole compound and application thereof in plant sterilization | |
| CN106212487A (en) | A kind of 1,2,4 triazole derivatives containing methoxyl group benzopyrazines structure are as the application of antibacterial | |
| CN106243110A (en) | A kind of 1,2,4 triazole derivatives containing methoxyl group benzopyrazines structure and its preparation method and application | |
| JPH11302233A (en) | Fluorine-containing aniline compound | |
| CN106336415B (en) | A kind of 1,2,4- triazole derivatives of chloride benzopyrazines structure and its preparation method and application | |
| CN104650063B (en) | A kind of 2,4 dimethyl oxazoline base acrylonitrile compounds and its application | |
| CN110698462A (en) | 1,3, 5-substituent-4-pyrazole amide derivative and preparation method thereof | |
| CN103709175A (en) | One-step synthesis method of 6-chlorine-3H-oxazole [4,5-b] pyridine-2-ketone | |
| CN114716451B (en) | Frutinone compound and preparation method and application thereof |
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 a methylbenzopyrazine structure as a fungicide Granted publication date: 20190426 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 a methylbenzopyrazine structure as a fungicide Granted publication date: 20190426 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 a methylbenzopyrazine structure as a fungicide Granted publication date: 20190426 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 a methylbenzopyrazine structure as a fungicide Granted publication date: 20190426 License type: Common License Record date: 20230828 |