CN106220633A - 1,2,4 triazole derivatives of a kind of chloride benzopyrazines structure are as the application of antibacterial - Google Patents
1,2,4 triazole derivatives of a kind of chloride benzopyrazines structure are as the application of antibacterial Download PDFInfo
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Abstract
The invention discloses 1,2,4 triazole derivatives application as antibacterial of a kind of chloride benzopyrazines structure.It generates compound (II) with 4 chlorine ortho-nitranilines with hydrazine hydrate, then reacts with MBF, obtains product (III), compound (III) is used POCl3Chlorination obtains product (IV), and compound thing (IV) and hydrazine hydrate react to obtain intermediate product (V), and compound (V) is with POCl3Make solvent, react to obtain 1,2,4 triazole derivatives of the chloride 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 technical fields, it is specifically related to the 1 of a kind of chloride benzopyrazines structure,
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 system of the 1,2,4-triazole derivative of a kind of chloride benzopyrazines structure with bactericidal activity
Preparation Method and application technology.
Summary of the invention
It is an object of the present invention to provide 1,2,4-triazole derivative the answering as antibacterial of a kind of chloride benzopyrazines structure
With.
1,2,4-triazole derivatives of described a kind of chloride benzopyrazines structure are as the application of antibacterial, and its feature exists
In its structural formula as shown in (I):
Wherein: R1For phenyl, undecyl, 3-chloropyridine, 4-n-pro-pyl phenyl, 4-aminomethyl phenyl, 4-isopropyl phenyl,
4-fluorophenyl, 2-fluorophenyl, 4-tert-butyl-phenyl, 2,4-Dichlorobenzene base, 4-nitrobenzophenone, 4-methoxyphenyl, 2-methoxyl group
Phenyl, 2-aminomethyl phenyl, 3-aminomethyl phenyl, 2-iodobenzene, 2-furan.
The 1,2,4-triazole derivative of described chloride benzopyrazines structure is preventing and treating fungus point spore anthrax as antibacterial
Application in bacterium, Fructus Fragariae Ananssae anthrax, Fructus Lycii anthrax bacteria.
Described application, it is characterised in that the R in 1,2,4-triazole derivatives of chloride benzopyrazines structure1For phenyl,
Undecyl, 3-chloropyridine, 4-n-pro-pyl phenyl, 4-aminomethyl phenyl, 4-fluorophenyl, 2-fluorophenyl, 4-tert-butyl-phenyl, 2,4-
Dichlorobenzene base, 4-nitrobenzophenone, 2-aminomethyl phenyl, 3-aminomethyl phenyl, 2-iodobenzene.
The preparation method of 1,2,4-triazole derivatives of described a kind of chloride benzopyrazines structure, it is characterised in that include
Following steps:
1) being solvent at methanol, Raney Ni is under catalysts conditions, and 4-chloro-2-nitroaniline is heated to reflux with hydrazine hydrate
Prepare 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
Chlorination reaction is carried out under the conditions of stream, after TLC monitoring reaction terminates, the post-treated compound (IV) obtained as shown in formula IV,
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-chloro-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 of the chloride benzopyrazines structure shown in formula (I)；
Preparation process is as follows:
The preparation method of 1,2,4-triazole derivatives of described chloride benzopyrazines structure, it is characterised in that step 1)
In, each material inventory of addition is: 0.1mol 4-chloro-2-nitroaniline, 30-50mL methanol, the hydration of 70-80mL85%
Hydrazine, 0.25～0.45g Raney Ni are preferably 0.1mol 4-chloro-2-nitroaniline, 40mL methanol, the hydration of 75mL85%
Hydrazine, 0.25～0.45g Raney Ni, Raney Ni is weight in wet base.
The preparation method of 1,2,4-triazole derivatives of described chloride benzopyrazines structure, it is characterised in that step 2)
In, reaction temperature is room temperature, and the response time is 30-90min.
The preparation method of 1,2,4-triazole derivatives of described chloride benzopyrazines structure, it is characterised in that step 3)
In, post-processing approach is to be poured slowly in frozen water by reactant liquor after completion of the reaction, separates out a large amount of yellow solid immediately, sucking filtration,
Washing is dried, and obtains compound (IV).
The preparation method of 1,2,4-triazole derivatives of described chloride benzopyrazines structure, it is characterised in that step 4)
In, compound (IV) is 1:3-3.2, preferably 1:3 with the molar ratio of the hydrazine hydrate of 85%.
The preparation method of 1,2,4-triazole derivatives of described chloride 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 1,2,4-triazole derivatives of described chloride 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 developing solvent, what monitoring was reacted carries out degree.
The 1,2,4-triazole derivative of described chloride benzopyrazines structure is as the application of herbicide.
Compared with prior art, the beneficial effects are mainly as follows: the invention provides a kind of chloride benzo pyrrole
The 1 of piperazine 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, the preventing and treating of 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) of the chloride 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-chloro-2-nitroaniline, 40mL methanol, 75mL hydrazine hydrate
(85%), 0.25～0.45g Raney Ni (weight in wet base), be heated to reflux, follow the trail of with TLC and disappear to raw material, reaction cools down after terminating
To room temperature, being filtered to remove Raney Ni, decompression is distilled off solvent and obtains filbert crystal, obtains the 4-chlorine neighbour's benzene shown in formula II
Diamidogen.0.1mol 4-chlorine o-phenylenediamine (II), use 100mL ethanol are dissolved, then are slowly added dropwise MBF, when reacting at normal temperatures
Between section be 30-90min, after reaction completely, be filtered to remove solvent, with alcohol flushing three times product (III).By compound (III)
Join in 100mL single port flask, and use 40mL POCl3Do and under solvent, heated reflux condition, carry out chlorination, after reaction terminates
Being cooled to room temperature, be poured slowly in 500g frozen water, separate out a large amount of yellow solid immediately, sucking filtration, washing are dried, and obtain product
(Ⅳ).Make solvent with 60mL ethanol, product (IV) is slowly added dropwise the hydrazine hydrate of 18g (0.3mol) 85%, after dropping
Being warming up to backflow, react 4-5h, reaction is cooled to room temperature after terminating, pours in 300g frozen water, separate out a large amount of white solid immediately,
Through sucking filtration, wash and be dried, prepare thick product, obtain intermediate product (V) by recrystallization.By compound (V) with POCl3Do molten
Agent, reacts to obtain 1,2,4-triazole derivatives of the chloride benzopyrazines structure shown in formula (I) with replacing acid compounds.
Embodiment 1～17, the acids synthesis compound 1～17 different from substituent group is as follows, other synthesis condition
Do not change.
Embodiment 1
Chloro-Isosorbide-5-Nitrae-the diphenyl of 8--[1,2,4] triazole [4,3-a] quinoxaline, yield 66.2%, fusing point 200-203 DEG C；1H
NMR (400MHZ, CDCl3/TMS), δ 7.47 (m, 1H, Ph-H), 7.56 (d, J=5.6Hz, 1H, Ph-H), 7.66 (m, 3H, Ph-
H), 7.67-7.71 (m, 5H, Ph-H), 8.15 (d, J=6.8Hz, 1H, Ph-H), 8.90 (m, 2H, Ph-H) .HRMS (ESI) m/
z:Calculated,379.0721,Found,379.0727[M+H]+.
Embodiment 2
8-chloro-4-phenyl-1-undecyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 67.8%, fusing point 107-
111℃；1H NMR (400MHZ, CDCl3/TMS), δ 0.90 (t, J=6.0Hz, 3H, CH3), 1.47 (m, 14H, CH2), 1.63
(m, J=5.6Hz, 2H, CH2), 2.10 (m, J=6.0Hz, 2H, CH), 3.50 (m, 2H, CH2), 7.60-7.66 (m, 4H, Ph-
H),8.07-8.23(m,2H,Ph-H),8.84(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,435.2310,
Found,435.2385[M+H]+.
Embodiment 3
The chloro-1-of 8-(3-chloropyridine)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 76.9%, fusing point 116-
119℃；1H NMR(400MHZ,CDCl3/TMS),δ7.41(m,1H,Ph-H),7.62-7.67(m,5H,Ph-H),8.14(m,
1H,Ph-H),8.26(m,1H,Py-H),8.82(m,1H,Py-H),8.92(m,2H,1Ph-H,1Py-H).HRMS(ESI)m/z:
Calculated,392.0464,Found,392.0 473[M+H]+.
Embodiment 4
8-chloro-4-phenyl-1-(4-n-pro-pyl phenyl)-[1,2,4] triazole [4,3-a] quinoxaline, yield 55.3%, fusing point
70-74℃；1H NMR (400MHZ, CDCl3/TMS), δ 0.97 (t, J=6.0Hz, 3H, CH3), 1.70 (m, J=6.0Hz, 2H,
CH2), 2.68 (t, J=6.4Hz, 2H, CH2), 7.30 (m, 2H, Ph-H), 7.48-7.57 (m, 3H, Ph-H), 7.14 (m, 4H,
Ph-H), 8.05 (d, J=6.4Hz, 2H, Ph-H), 8.89 (m, 1H, Ph-H) .HRMS (ESI) m/z:Calculated,
399.1371,Found,399.1375[M+H]+.
Embodiment 5
8-chloro-4-phenyl-1-p-methylphenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 83.8%, fusing point 105-
108℃；1H NMR(400MHZ,CDCl3/TMS),δ2.46(s,3H,CH3),7.30(s,1H,Ph-H),7.46-7.66(m,
7H, Ph-H), 8.02 (d, J=6.4Hz, 2H, Ph-H), 8.20 (m, 1H, Ph-H), 8.90 (m, 1H, Ph-H) .HRMS (ESI) m/
z:Calculated,371.1058,Found,371.1062[M+H]+.
Embodiment 6
8-chloro-4-phenyl-1-(4-isopropyl phenyl)-[1,2,4] triazole [4,3-a] quinoxaline, yield 59.7%, fusing point
57-58℃；1H NMR (400MHZ, CDCl3/TMS), δ 1.29-1.41 (m, 6H, CH3), 3.12 (m, J=5.6Hz, 1H, CH),
7.33 (d, J=6.4Hz, 1H, Ph-H), 7.50-7.59 (m, 3H, Ph-H), 7.64 (m, 3H, Ph-H), 7.65 (d, J=
6.0Hz, 1H, Ph-H), 7.74 (m, 1H, Ph-H), 8.03 (d, J=6.4Hz, 1H, Ph-H), 8.14 (m, 1H, Ph-H), 8.89
(m,1H,Ph-H).HRMS(ESI)m/z:Calculated,399.1371,Found,399.1369[M+H]+.
Embodiment 7
The chloro-1-of 8-(4-fluorophenyl)-4-phenyl--[1,2,4] triazole [4,3-a] quinoxaline, yield 71.8%, fusing point
159-163℃；1H NMR (400MHZ, CDCl3/TMS), δ 7.18 (t, J=8.3Hz, 1H, Ph-H), 7.37 (m, 2H, Ph-H),
7.64(m,3H,Ph-H),7.77(m,2H,Ph-H),8.15(m,2H,Ph-H),8.88(m,2H,Ph-H).HRMS(ESI)m/z:
Calculated,375.0807,Found,375.0818[M+H]+.
Embodiment 8
The chloro-1-of 8-(2-fluorophenyl)-4-phenyl--[1,2,4] triazole [4,3-a] quinoxaline, yield 60.4%, fusing point
175-180℃；1H NMR (400MHZ, CDCl3/TMS), δ 7.43-7.70 (m, 9H, Ph-H), 8.17 (d, J=7.2Hz, 1H,
Ph-H),8.89(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,375.0807,Found,375.0817[M+H]+.
Embodiment 9
1-(4-tert-butyl-phenyl)-8-chloro-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 75.2%, fusing point
200-203℃；1H NMR(400MHZ,CDCl3/TMS),δ1.13(s,9H,CH3),7.50(m,2H,Ph-H),7.64(m,3H,
Ph-H),7.70(m,3H,Ph-H),8.04(m,2H,Ph-H),8.89(m,2H,Ph-H).HRMS(ESI)m/z:
Calculated,413.1528,Found,413.1534[M+H]+.
Embodiment 10
1-(2,4-Dichlorobenzene base)-8-chloro-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 71.8%, fusing point
198-201℃；1H NMR(400MHZ,CDCl3/TMS),δ7.41(m,1H,Ph-H),7.59-7.76(m,7H,Ph-H),8.18
(d, J=6.8Hz, 1H, Ph-H), 8.91 (m, 2H, Ph-H) .HRMS (ESI) m/z:Calculated, 425.0122, Found,
425.0127[M+H]+. embodiment 11
1-(4-nitrobenzophenone)-8-chloro-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 80.0%, fusing point
197-200℃；1H NMR(400MHZ,CDCl3/TMS),δ7.52(m,1H,Ph-H),7.66(m,3H,Ph-H),8.04(t,J
=7.2Hz, 2H, Ph-H), 8.26 (m, 1H, Ph-H), 8.35 (t, J=6.8Hz, 1H, Ph-H), 8.57 (m, 2H, Ph-H),
8.90(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,372.1010,Found,402.0752[M+H]+.
Embodiment 12
1-(4-methoxyphenyl)-8-chloro-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 93.5%, fusing point
110-113℃；1H NMR(400MHZ,CDCl3/TMS),δ4.00(m,3H,OCH3),7.56(m,1H,Ph-H),7.63(m,
3H, Ph-H), 7.68 (t, J=7.2Hz, 2H, Ph-H), 8.09 (d, J=6.8Hz, 4H, Ph-H), 8.88 (m, 2H, Ph-H)
.HRMS(ESI)m/z:Calculated,387.1007,Found,387.102 5[M+H]+.
Embodiment 13
1-(2-methoxyphenyl)-8-chloro-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 68.2%, fusing point
79-82℃；1H NMR (400MHZ, CDCl3/TMS), δ 3.72 (m, 3H, OCH3), 7.34 (m, 1H, Ph-H), 7.43 (d, J=
7.2Hz, 1H, Ph-H), 7.49 (d, J=5.6Hz, 1H, Ph-H), 7.57 (m, 1H, Ph-H), 7.64 (m, 3H, Ph-H), 7.74
(m,2H,Ph-H),8.20(m,1H,Ph-H),8.90(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,387.1007,
Found,387.1012[M+H]+.
Embodiment 14
1-o-tolyl-8-chloro-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 61.5%, fusing point 107-
111℃；1H NMR (400MHZ, CDCl3/TMS), δ 2.67 (s, 3H, CH3), 7.50 (d, J=7.8Hz, 2H, Ph-H), 7.56
(d, J=6.6Hz, 2H, Ph-H), 7.65 (m, 4H, Ph-H), 8.07 (d, J=7.0Hz, 1H, Ph-H), 8.21 (m, 1H, Ph-
H),8.93(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,371.1058,Found,371.1066[M+H]+.
Embodiment 15
Tolyl-8-chloro-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 56.8%, fusing point 120-between 1-
123℃；1H NMR (400MHZ, CDCl3/TMS), δ 2.44 (s, 3H, CH3), 7.39 (d, J=6.0Hz, 1H, Ph-H), 7.45
(d, J=6.0Hz, 1H, Ph-H), 7.54 (m, 2H, Ph-H), 7.57 (m, 1H, Ph-H), 7.64 (m, 3H, Ph-H), 7.91 (s,
1H,Ph-H),8.21(m,1H,Ph-H),8.90(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,371.1058,
Found,371.1075[M+H]+.
Embodiment 16
1-(2-iodophenyl)-8-chloro-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 65.3%, fusing point 67-
70℃；1H NMR(400MHZ,CDCl3/TMS),δ7.45-7.49(m,2H,Ph-H),7.64-7.69(m,5H,Ph-H),8.00
(d, J=6.4Hz, 1H, Ph-H), 8.07 (d, J=6.0Hz, 1H, Ph-H), 8.16 (d, J=7.2Hz, 1H, Ph-H), 8.96
(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,482.9868,Found,482.9879[M+H]+.
Embodiment 17
1-(furan-2-base)--8-chloro-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 33.1%, fusing point
136-139℃；1H NMR(400MHZ,CDCl3/TMS),δ6.82(m,1H,furan-H),7.22(m,1H,furan-H),
7.42(m,1H,Ph-H),7.64(m,4H,Ph-H),7.97(m,1H,Ph-H),8.23(m,1H,Ph-H),8.87(m,2H,
1furan-H,1Ph-H).HRMS(ESI)m/z:Calculated,347.0694,Found,347.0714[M+H]+.
Embodiment 18
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.
Lived in point spore anthrax, Fructus Fragariae Ananssae anthrax, the indoor of 3 antibacterial targets such as Fructus Lycii anthrax bacteria by compound 1-17
Body the selection result is shown in Table 1.
The bactericidal activity data of table 1 compound D1-D17
Knowable to above-mentioned table 1, this compounds sets under concentration the bactericidal activity testing selected 3 kinds of targets in test.
Wherein 2,3,4,5 pairs of fungus point spore anthrax bacterias of compound, Strawberry anthracnose bacterium and Fructus Lycii anthrax bacteria have preferable activity, chemical combination
1,7,8,9,10,11,14,15,16 pairs of fungus point spore anthrax bacterias of thing, Strawberry anthracnose bacterium and Fructus Lycii anthrax bacteria have certain living
Property.
Claims (3)
1. 1,2,4-triazole derivatives of a chloride benzopyrazines structure are as the application of antibacterial, it is characterised in that its structure
Formula is as shown in (I):
Wherein: R1For phenyl, undecyl, 3-chloropyridine, 4-n-pro-pyl phenyl, 4-aminomethyl phenyl, 4-isopropyl phenyl, 4-fluorine
Phenyl, 2-fluorophenyl, 4-tert-butyl-phenyl, 2,4-Dichlorobenzene base, 4-nitrobenzophenone, 4-methoxyphenyl, 2-methoxyphenyl,
2-aminomethyl phenyl, 3-aminomethyl phenyl, 2-iodobenzene, 2-furan.
2. the 1,2,4-triazole derivative of a chloride benzopyrazines structure according to claim 1 is being prevented as antibacterial
Control the application in fungus point spore anthrax, Fructus Fragariae Ananssae anthrax, Fructus Lycii anthrax bacteria.
Application the most according to claim 1, it is characterised in that in 1,2,4-triazole derivatives of chloride benzopyrazines structure
R1For phenyl, undecyl, 3-chloropyridine, 4-n-pro-pyl phenyl, 4-aminomethyl phenyl, 4-fluorophenyl, 2-fluorophenyl, the tertiary fourth of 4-
Base phenyl, 2,4-Dichlorobenzene base, 4-nitrobenzophenone, 2-aminomethyl phenyl, 3-aminomethyl phenyl, 2-iodobenzene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610613110.4A CN106220633B (en) | 2016-07-28 | 2016-07-28 | A kind of application of 1,2,4- triazole derivatives of the structure of benzopyrazines containing chlorine as fungicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610613110.4A CN106220633B (en) | 2016-07-28 | 2016-07-28 | A kind of application of 1,2,4- triazole derivatives of the structure of benzopyrazines containing chlorine as fungicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106220633A true CN106220633A (en) | 2016-12-14 |
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| CN101016300A (en) * | 2007-02-14 | 2007-08-15 | 浙江工业大学 | Triazole pyrimidine sulphonates compound, preparing method and application thereof |
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| MOHAMMED SALAH AYOUP ET AL.: "Synthesis, Docking, and Evaluation of Antimicrobial Activity of a New Series of Acyclo C-Nucleosides of 1, 2, 4-Triazolo[4, 3-a]quinoxaline Derivatives", 《JOURNAL OF HETEROCYCLIC CHEMISTRY》 * |
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| 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 |
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Application publication date: 20161214 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 chlorobenzopyrazine structure as a fungicide Granted publication date: 20180831 License type: Common License Record date: 20230316 Application publication date: 20161214 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 chlorobenzopyrazine structure as a fungicide Granted publication date: 20180831 License type: Common License Record date: 20230316 Application publication date: 20161214 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 chlorobenzopyrazine structure as a fungicide Granted publication date: 20180831 License type: Common License Record date: 20230315 |
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Application publication date: 20161214 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 chlorobenzopyrazine structure as a fungicide Granted publication date: 20180831 License type: Common License Record date: 20230828 |