CN106234385B - A kind of application of 1,2,4- triazole derivatives of the structure containing benzopyrazines as fungicide - Google Patents
A kind of application of 1,2,4- triazole derivatives of the structure containing benzopyrazines as fungicide Download PDFInfo
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- CN106234385B CN106234385B CN201610608888.6A CN201610608888A CN106234385B CN 106234385 B CN106234385 B CN 106234385B CN 201610608888 A CN201610608888 A CN 201610608888A CN 106234385 B CN106234385 B CN 106234385B
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- 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
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Abstract
Application the invention discloses a kind of 1,2,4- triazole derivatives of structure containing benzopyrazines as fungicide.It generates compound (II) with ortho-nitraniline and hydrazine hydrate.It is reacted again with MBF, obtains product (III).Compound (III) is used into POCl3Chlorination obtains product (IV).Compound object (IV) obtains intermediate product (V) with hydration hydrazine reaction.Compound (V) is with POCl3Make solvent, reacted with substitution acid compounds the structure containing benzopyrazines shown in formula (I) 1,2,4- triazole derivatives；Its raw material is simple and easy to get, preparation method is simple, convenient post-treatment, and product yield is high, and the compound is with bactericidal activity, especially the prevention of fungi point spore anthrax bacteria, Strawberry anthracnose bacterium and matrimony vine anthrax bacteria etc. has good effect, provides the foundation for the research and development of novel pesticide.
Description
Technical field
The invention belongs to 1,2,4- triazole class compounds preparing technical fields, and in particular to a kind of structure containing benzopyrazines
Application of the 1,2,4- triazole derivatives as fungicide.
Background technology
The synthesis of quinoxaline, triazole compound is chemistry of pesticide, iatrochemistry, polymer chemistry, Coordinative Chemistry
Important directions.Quinoxaline compound has significant bioactivity, is widely used in the fields such as pesticide, medicine, dyestuff.Three
Nitrogen azole compounds are again because its good sterilization, weeding, desinsection and plant growth regulating activity are applied in pesticide field.Some reports
Road, which shows fused heterocyclic compound usually, has the mixed attributes of single heterocycle.In order to find high-efficiency activated noval chemical compound, in benzo
Splice upper triazole structure in pyrazine structure, synthesizes novel 1 with bactericidal activity, 2,4- triazole derivatives.
The present invention provides a kind of preparations of the 1,2,4- triazole derivatives of structure containing benzopyrazines with bactericidal activity
Method and application technology.
Invention content
It is an object of the present invention to provide a kind of 1,2,4- triazole derivatives of structure containing benzopyrazines with bactericidal activity and
Preparation method and application.
The 1 of a kind of structure containing benzopyrazines, application of 2, the 4- triazole derivatives as fungicide, it is characterised in that
Its structural formula is such as shown in (I)：
Wherein：R1For phenyl, 4- n-propyl phenyl, 4- aminomethyl phenyls, 2,4- dichlorophenyls, 2- chloropyridines, 4- hydroxy benzenes
Base, undecyl, methylamino, 3- pyridines, 4- nitrobenzophenones, 4- tert-butyl-phenyls, 4- methoxyphenyls, 4- aminophenyls, 2-
Furans, 2- pyridines.
The 1,2,4- triazole derivatives of the structure containing benzopyrazines are as prevention fungi point spore anthrax-bacilus, strawberry anthrax
The application of the fungicide of bacterium matrimony vine anthrax bacteria.
The application, it is characterised in that 1- (4- methylphenethyls) -4- phenyl-[1,2,4] triazole [4,3-a] quinoline
Quinoline, 4- phenyl -1- p-methylphenyls-[1,2,4] triazole [4,3-a] quinoxaline are to fungi point spore anthrax bacteria, Strawberry anthracnose bacterium
There is good activity with matrimony vine anthrax bacteria.
The application, it is characterised in that 1- (2,4- dichlorophenyl) -4- phenyl-[1,2,4] triazole [4,3-a] quinoline
Quinoline, 4- (4- phenyl-[1,2,4] triazole [4,3-a] quinoxaline -1- bases) phenol, 4- phenyl -1- undecyls-[1,2,4] triazole
[4,3-a] quinoxaline, (4- phenyl-[1,2,4] triazole [4,3-a] quinoxaline -1- bases) methylamine, 1- (4- (tertiary butyl) phenyl) -
4- phenyl-[1,2,4] triazole [4,3-a] quinoxaline is to fungi point spore anthrax bacteria, Strawberry anthracnose bacterium and matrimony vine anthrax bacteria
It is active.
The 1 of the structure containing benzopyrazines, the preparation method of 2,4- triazole derivatives, it is characterised in that including walking as follows
Suddenly：
1) it is solvent in methanol, Raney Ni are under catalysts conditions, and ortho-nitraniline is heated to reflux obtained with hydrazine hydrate
Such as formula (II) compound represented (II)；
2) compound (II) and methyl benzoylformate reaction the synthesis chemical combination as shown in formula (III) obtained step 1)
Object (III) crude product；
3) compound (III) crude product obtained step 2) washs after purification through ethyl alcohol, uses POCl3Solvent is made, is heated back
Chlorination reaction is carried out under the conditions of stream, post-processing is obtained such as formula (IV) compound represented (IV)；
4) using ethyl alcohol as solvent, the compound (IV) that step 3) obtains is obtained with hydration hydrazine reaction and is changed shown in formula (V)
Close object (V) crude product；
5) compound (V) crude product obtained step 4) is after recrystallization purifying, with POCl3Solvent is made, with substitution acid
Class compound react the structure containing benzopyrazines shown in formula (I) 1,2,4- triazole derivatives；
Its preparation process is as follows：
The 1 of the structure containing benzopyrazines, the preparation method of 2,4- triazole derivatives, it is characterised in that in step 1),
The inventory of each substance being added is：0.1mol ortho-nitranilines, 30-50mL methanol, 70-80mL hydrazine hydrates (85%), 0.25
~0.45g Raney Ni, preferably 0.1mol ortho-nitranilines, 40mL methanol, 75mL hydrazine hydrates (85%), 0.25~0.45g
Raney Ni, Raney Ni are weight in wet base.
The 1 of the structure containing benzopyrazines, the preparation method of 2,4- triazole derivatives, it is characterised in that in step 2),
Compound (II) is firstly dissolved in alcohol, and the volumetric usage of ethyl alcohol is calculated as 0.8~1.2ml/mmol with the amount of compound (II) substance,
Reaction temperature is room temperature, reaction time 30-90min.
The 1 of the structure containing benzopyrazines, the preparation method of 2,4- triazole derivatives, it is characterised in that after in step 3)
Processing procedure is：Reaction solution is poured slowly into ice water, a large amount of yellow solids are precipitated, is filtered, washing is dried to obtain compound
(Ⅳ)。
The 1 of the structure containing benzopyrazines, the preparation method of 2,4- triazole derivatives, it is characterised in that in step 4),
The molar ratio of compound (IV) and 85% hydrazine hydrate is 1：2-4.
The 1 of the structure containing benzopyrazines, the preparation method of 2,4- triazole derivatives, it is characterised in that compound (V)
It is 1 with the ratio between the amount of substance for replacing acid compounds:1-1.2 is heated to reflux 3.5-4.5h, preferably 4h.
The 1 of the structure containing benzopyrazines, the preparation method of 2,4- triazole derivatives, it is characterised in that in step 3),
When carrying out TLC monitorings, extracts reaction solution to be added in ice water and crack POCl3, then product is extracted with ethyl acetate, take organic layer, with
Ethyl acetate：Petroleum ether=1:3 mixed liquors are solvent, monitor the carry out degree of reaction.
Compared with prior art, the beneficial effects are mainly as follows：The present invention provides one kind containing benzopyrazines
The 1 of structure, application of 2, the 4- triazole derivatives as fungicide, raw material is simple and easy to get, and preparation method is simple, post-processing side
Just, product yield is high, and the compound is with bactericidal activity, especially for prevention fungi point spore anthrax-bacilus, strawberry charcoal
Subcutaneous ulcer bacterium, matrimony vine anthrax bacteria etc. have good effect, provide the foundation for the research and development of novel pesticide.
Specific implementation mode
With reference to 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 derivatives (I) of the structure containing benzopyrazines of the present invention can synthesize in the following manner：
In 250mL single-necked flasks, sequentially add 0.1mol ortho-nitranilines, 40mL methanol, 75mL hydrazine hydrates (85%),
0.25~0.45g Raney Ni (weight in wet base), are heated to reflux, and are tracked to raw material and are disappeared with TLC, are cooled to room temperature after reaction,
It is filtered to remove RaneyNi, vacuum distillation removes solvent and obtains filbert crystal, obtains o-phenylenediamine shown in formula (II).0.1mol
O-phenylenediamine (II) is dissolved with 100mL ethyl alcohol, then MBF is slowly added dropwise, and reaction time section is 30-90min at normal temperatures,
After the reaction was complete, it is filtered to remove solvent, product (III) is flushed three times to obtain with ethyl alcohol.Compound (III) is added to 100mL single port
In flask, 40mL POCl are used in combination3Solvent is made, chlorination is carried out under heated reflux condition, is cooled to room temperature after reaction, slowly
It pours into 500g ice water, a large amount of yellow solids is precipitated immediately, filter, washing drying, obtain product (IV).It is made of 60mL ethyl alcohol molten
The hydrazine hydrate of 18g (0.3mol) 85% is slowly added dropwise in agent in product (IV), and reflux is warming up to after being added dropwise, and reacts 4-5h,
It is cooled to room temperature, is poured into 300g ice water after reaction, a large amount of white solids are precipitated immediately, through suction filtration, washing and drying, system
Crude product is obtained, by recrystallizing to obtain intermediate product (V).By compound (V) with POCl3Solvent is made, with substitution acid compounds
React the structure containing benzopyrazines shown in formula (I) 1,2,4- triazole derivatives.
Embodiment 1~16, the acids different from substituent group synthesize compound 1~16 as follows, other synthesis conditions
Do not change.
Embodiment 1
Isosorbide-5-Nitrae-diphenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 71.8%, 200-203 DEG C of fusing point；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- methylphenethyls) -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-methylphenyls-[1,2,4] triazole [4,3-a] quinoxaline, yield 55.6%, 90-93 DEG C of fusing point；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- dichlorophenyl) -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- bases) -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- bases) 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- undecyls-[1,2,4] triazole [4,3-a] quinoxaline, yield 72.5%, 93-96 DEG C of fusing point；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- bases) methylamine, yield 37.2%, 153-155 DEG C of fusing point；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- nitrobenzophenones) -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- (tertiary butyl) 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- anisyls) -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- bases) 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- (furans -2- bases) -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- bases)-[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- fluorophenyls) -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]+.
17 bactericidal activity of embodiment is tested
Subjects：Fungi point spore anthrax-bacilus, strawberry anthrax-bacilus, matrimony vine anthrax bacteria.
Test method：The preparation and preservation of pathogen:Test fungi point spore anthrax-bacilus (Colletrotichum anthrax
), CaGoff strawberry anthrax-bacilus (Colletrotichum fragariae Cf63), matrimony vine anthrax bacteria (Colletrotichum
Gloeosporioides Cg162) it is stored in natural products research on utilization institute of agricultural research institute of the Ministry of Agriculture of United States Department of Agriculture
(USDA-ARS, Natural Products Utilization Research Unit) David Wedge seminars.Three kinds of charcoals
Subcutaneous ulcer strain is isolated from strawberry.
Inoculation method：The conidium of each fungal species is gently brushed into lamellae with a L-shaped glass bar.
Direct bioautography：After Deng test, the radius size of thin-layer chromatography version is measured.
Compound 1-16 is to fungi point spore anthrax-bacilus, strawberry anthrax-bacilus, the room of 3 fungicide targets such as matrimony vine anthrax bacteria
Interior Vivo Studies on Screening the results are shown in Table 1.
The bactericidal activity data of 1 compound 1-16 of table
From above-mentioned table 1 it is found that compound in the case where experiment sets concentration to testing the bactericidal activities of selected 3 kinds of targets.Chemical combination
Object 2,3 has fungi point spore anthrax bacteria, Strawberry anthracnose bacterium and matrimony vine anthrax bacteria under the conditions of microtitration good
Activity, compound 4,6,7,8,11 pairs of fungi point spore anthrax bacterias, Strawberry anthracnose bacterium and matrimony vine anthrax bacteria have certain activity.
Claims (4)
1. the 1,2,4- triazole derivatives of structure containing benzopyrazines a kind of as prevention fungi point spore anthrax-bacilus, strawberry anthrax-bacilus,
The application of the fungicide of matrimony vine anthrax bacteria, it is characterised in that its structural formula is such as shown in (I)：
Wherein：R1For 4- n-propyl phenyl, 4- aminomethyl phenyls, 2,4- dichlorophenyls, 4- hydroxy phenyls, 4- tert-butyl-phenyls.
2. the 1,2,4- triazole derivatives of structure containing benzopyrazines a kind of are killed as prevention strawberry anthrax-bacilus, matrimony vine anthrax bacteria
The application of microbial inoculum, it is characterised in that its structural formula is such as shown in (I)：
Wherein：R1For phenyl.
3. a kind of 1,2,4- triazole derivatives of structure containing benzopyrazines are as prevention fungi point spore anthrax-bacilus, matrimony vine anthrax bacteria
Fungicide application, it is characterised in that its structural formula is such as shown in (I)：
Wherein：R1For 4- methoxyphenyls.
4. a kind of 1,2,4- triazole derivatives of structure containing benzopyrazines are answered as the fungicide for preventing fungi point spore anthrax-bacilus
With, it is characterised in that its structural formula is such as shown in (I)：
Wherein：R1For 2- pyridines.
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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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| 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)
| Title |
|---|
| 1，2，4-三唑类化合物杀菌活性的研究进展;王献友等;《江苏农业科学》;20131231;第41卷(第8期);第134-137页 * |
| 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;Eakta et al.;《Indian Journal of Chemistry》;20130228;第52B卷(第2期);第273-281页 * |
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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 |
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