CN106243110A - A kind of 1,2,4 triazole derivatives containing methoxyl group benzopyrazines structure and its preparation method and application - Google Patents
A kind of 1,2,4 triazole derivatives containing methoxyl group benzopyrazines structure and its preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of 1,2,4 triazole derivatives containing methoxyl group benzopyrazines structure and its preparation method and application.It generates compound (II) with 4 methoxyl group 2 nitroanilines 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 methoxyl group benzopyrazines structure shown in formula (I) with replacing acid compounds；Its raw material is simple and easy to get, and preparation method is simple, convenient post-treatment, and product yield is high, and this compound is for having activity of weeding, has good herbicidal effect especially for creeping bentgrass, provides the foundation for novel pesticide research and development.
Description
Technical field
The invention belongs to 1,2,4-triazole class compounds preparing technical fields, it is specifically related to a kind of benzopyrazines Han methoxyl group
1,2,4-triazole derivative of structure and its preparation method and application.
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 4 class benzene
And in pyrazine structure, splice triazole structure, synthesis has novel 1,2, the 4-triazole derivatives of activity of weeding.
The invention provides a kind of 1,2,4-triazole derivative containing methoxyl group benzopyrazines structure with activity of weeding
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 methoxyl group benzopyrazines structure and preparation side thereof
Method and application.
Described a kind of 1,2,4-triazole derivatives containing methoxyl group benzopyrazines structure, it is characterised in that its structural formula is such as
(I) shown in:
Wherein: R1For phenyl, undecyl, 3-fluorophenyl, 4-amyl group phenyl, 4-nitrobenzophenone, 3-nitrobenzophenone, 4-first
Phenyl, 4-isopropyl phenyl, 2-chloropyridine, 4-n-pro-pyl phenyl, 2-furan, 2,4-Dichlorobenzene base, 3-chlorphenyl, 4-fluorine
Phenyl, 3-aminomethyl phenyl.
The preparation method of described 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure, it is characterised in that include
Following steps:
1) being solvent at methanol, Raney Ni is under catalysts conditions, and 4-methoxyl group-2-nitroaniline heats with hydrazine hydrate
Backflow 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
Carry out chlorination reaction under the conditions of stream, terminate through TLC monitoring reaction, 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 shown in acquisition formula (V)
(7-methoxyl group-3-phenyl quinoxaline-2-base) hydrazine crude product (V)；
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 methoxyl group benzopyrazines structure shown in formula (I)；
Preparation process is as follows:
The preparation method of described 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure, it is characterised in that step
1), in, each material inventory of addition is: 0.1mol 4-methoxyl group ortho-nitraniline, 30-50mL methanol, 70-80mL85%
Hydrazine hydrate, 0.25～0.45g Raney Ni, preferably 0.1mol 4-methoxyl group ortho-nitraniline, 40mL methanol, 75mL85%
Hydrazine hydrate, 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 methoxyl group benzopyrazines structure, it is characterised in that step
2) reaction temperature in is room temperature, and the response time is 30-90min.
The preparation method of described 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure, it is characterised in that step
3) in, post-processing approach is: be poured slowly into after completion of the reaction in frozen water, separates out a large amount of yellow solid immediately, and sucking filtration, washing are dried,
Obtain compound (IV).
The preparation method of described 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure, it is characterised in that step
4), in, compound (IV) is 1:2.5-3.5, preferably 1:3 with the molar ratio of the hydrazine hydrate of 85%.
The preparation method of described 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure, it is characterised in that chemical combination
Thing (V) is 1:1:1.2 with the ratio of the amount of the material of replacing acid compounds, and the time of being heated to reflux is 3.5-4.54h, preferably thing
The ratio of the amount of matter is 1:1:1.2, and the time of being heated to reflux is 4h.
The preparation method of described 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure, it is characterised in that step
3), in, extract reaction solution during TLC monitoring, 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 described 1,2,4-triazole derivative containing methoxyl group benzopyrazines structure is as the application of herbicide.
The described 1,2,4-triazole derivative containing methoxyl group benzopyrazines structure is preventing and treating creeping bentgrass, life as herbicide
The application of dish weeds.
Compared with prior art, the beneficial effects are mainly as follows: the invention provides a kind of containing methoxybenzene
And 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
Method is simple, convenient post-treatment, and product yield is high, and this compound is for having activity of weeding, especially for preventing and treating Jian's stock
Grain husk, Caulis et Folium Lactucae Sativae weeds etc. there is good effect, the research and development for novel pesticide provide the foundation.
Compared with prior art, the beneficial effects are mainly as follows: the invention provides a kind of containing methoxybenzene
And 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
Method is simple, convenient post-treatment, and product yield is high, and this compound is for having activity of weeding, especially for preventing and treating Jian's stock
Grain husk, Caulis et Folium Lactucae Sativae weeds etc. there is good effect, 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 methoxyl group 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-methoxyl group-2-nitroaniline, 40mL methanol, 75mL water
Close hydrazine (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, react after terminating
Being cooled to room temperature, be filtered to remove Raney Ni, decompression is distilled off solvent and obtains filbert crystal, obtains the 4-shown in formula II and take
For o-phenylenediamine.0.1mol 4-methoxyl group o-phenylenediamine (II), use 100mL ethanol are dissolved, then are slowly added dropwise MBF, often
Temperature section of lower response time is 30-90min, after reaction completely, is filtered to remove solvent, obtains product (III) three times with alcohol flushing.Will
Compound (III) joins in 100mL single port flask, and uses 40mL POCl3Do and under solvent, heated reflux condition, carry out chlorination,
Reaction is cooled to room temperature after terminating, and is poured slowly in 500g frozen water, separates out a large amount of yellow solid immediately, and sucking filtration, washing are dried,
To product (IV).Make solvent with 60mL ethanol, product (IV) is slowly added dropwise the hydrazine hydrate of 18g (0.3mol) 85%, dropping
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
Color solid, through sucking filtration, washs and is dried, and prepares thick product, obtains intermediate product (V) by recrystallization.By compound (V) with
POCl3Make solvent, react to obtain 1,2, the 4-triazoles containing methoxyl group benzopyrazines structure shown in formula (I) with replacing acid compounds
Derivant.
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-methoxyl group-Isosorbide-5-Nitrae-diphenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 40.0%, fusing point 168-171
℃；1H NMR(400MHz,CDCl3/TMS),δ4.00(s,3H,OCH3),7.45-7.48(m,3H,Ph-H),7.56(m,3H,
Ph-H),7.63-7.71(m,3H,Ph-H),7.77(m,1H,Ph-H),7.88(m,2H,Ph-H),7.97(m,1H,Ph-H)
.HRMS(ESI)m/z:Calculated,353.1397,Found,353.1391[M+H]+.
Embodiment 2
8-methoxyl group-4-phenyl-1-undecyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 76.2%, fusing point
125-130℃；1H NMR (400MHZ, CDCl3/TMS), δ 0.90 (t, J=5.6Hz, 3H, CH3), 1.28 (m, 16H, CH2),
1.66 (m, J=6.0Hz, 2H, CH2), 2.37 (t, J=6.0Hz, 2H, CH2), 4.00 (s, 3H, OCH3), 7.46 (m, 2H, Ph-
H),7.56(m,3H,Ph-H),7.88(m,2H,Ph-H),7.97(m,1H,Ph-H).HRMS(ESI)m/z:Calculated,
431.2805,Found,431.2809[M+H]+.
Embodiment 3
1-(3-fluorophenyl)-8-methoxyl group-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 60.1%, fusing point
164-168℃；1H NMR(400MHZ,CDCl3/TMS),δ4.00(s,3H,OCH3),7.45-7.48(m,3H,Ph-H),
7.54-7.58(m,4H,Ph-H),7.63-7.70(m,2H,Ph-H),7.68(m,2H,Ph-H),7.97(m,1H,Ph-H)
.HRMS(ESI)m/z:Calculated,371.1303,Found,371.1307[M+H]+.
Embodiment 4
8-methoxyl group-1-(4-n-pentyl phenyl)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 64.3%,
Fusing point 90-94 DEG C；1H NMR (400MHZ, CDCl3/TMS), δ 4.00 (s, 3H, OCH3), 0.92 (t, J=5.2Hz, 3H,
CH3), 1.35 (m, 4H, CH2), 1.66 (m, J=6.0Hz, 2H, CH2), 2.70 (t, J=6.0Hz, 2H, CH2), 7.30 (d, J
=6.8Hz, 2H, Ph-H), 7.48 (s, 1H, Ph-H), 7.55 (m, 3H, Ph-H), 7.88 (m, 2H, Ph-H), 7.97 (d, J=
7.2Hz, 1H, Ph-H), 8.04 (d, J=6.4Hz, 2H, Ph-H) .HRMS (ESI) m/z:Calculated, 423.2179,
Found,423.2188[M+H]+.
Embodiment 5
8-methoxyl group-1-(4-nitrobenzophenone)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 70.0%, molten
Point 153-157 DEG C；1H NMR(400MHZ,CDCl3/TMS),δ4.00(s,3H,OCH3),7.47(m,2H,Ph-H),7.56(m,
3H,Ph-H),7.64(m,2H,Ph-H),7.87(m,2H,Ph-H),7.97(m,1H,Ph-H),8.06(m,1H,Ph-H),8.18
(m,1H,Ph-H).HRMS(ESI)m/z:Calculated,398.1248,Found,398.1263[M+H]+.
Embodiment 6
8-methoxyl group-1-(3-nitrobenzophenone)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 63.0%, molten
Point 144-149 DEG C；1H NMR(400MHZ,CDCl3/TMS),δ4.00(s,3H,OCH3),7.47(m,2H,Ph-H),7.56(m,
2H, Ph-H), 7.63 (m, 2H, Ph-H), 7.87 (m, 2H, Ph-H), 7.92 (t, J=6.4Hz, 1H, Ph-H), 7.97 (m, 1H,
Ph-H),8.19(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,398.1263,Found,398.1248[M+H]+.
Embodiment 7
8-methoxyl group-1-(4-methoxyphenyl)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 59.4%,
Fusing point 150-154 DEG C；1H NMR(400MHZ,CDCl3/TMS),δ3.91(s,3H,OCH3),4.00(s,3H,OCH3),7.47
(m, 2H, Ph-H), 7.55-7.62 (m, 3H, Ph-H), 7.72 (d, J=7.2Hz, 1H, Ph-H), 7.87 (m, 2H, Ph-H),
7.97(m,1H,Ph-H),8.09(m,3H,Ph-H).HRMS(ESI)m/z:Calculated,383.1503,Found,
383.1519[M+H]+.
Embodiment 8
1-(4-isopropyl phenyl)-8-methoxyl group-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 66.0%,
Fusing point 154-159 DEG C；1H NMR (400MHZ, CDCl3/TMS), δ 1.30 (d, J=5.6Hz, 6H, CH3), 3.01 (m, J=
5.6Hz, 1H, CH), 4.00 (s, 3H, OCH3), 7.34 (d, J=6.4Hz, 1H, Ph-H), 7.46-7.59 (m, 7H, Ph-H),
7.17 (m, 2H, Ph-H), 7.97 (d, J=8.0Hz, 1H, Ph-H), 8.04 (m, 1H, Ph-H) .HRMS (ESI) m/z:
Calculated,395.1866,Found,395.1876[M+H]+.
Embodiment 9
1-(2-chloropyridine-4-base)-8-methoxyl group-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield
40.0%, fusing point 127-131 DEG C；1H NMR(400MHZ,CDCl3/TMS),δ4.00(s,3H,OCH3),7.46(m,1H,Ph-
H),7.55(m,3H,Ph-H),7.60-7.65(m,3H,Ph-H),7.87(m,2H,Ph-H),7.97(m,1H,Ph-H),8.16
(m,1H,Ph-H).HRMS(ESI)m/z:Calculated,388.0960,Found,388.0964[M+H]+.
Embodiment 10
1-(4-n-pro-pyl phenyl)-8-methoxyl group-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 57.1%,
Fusing point 128-130 DEG C；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=6.0Hz, 2H, CH2), 4.00 (s, 3H, OCH3), 7.30 (d, J=6.4Hz, 2H, Ph-
H), 7.47 (m, 2H, Ph-H), 7.56 (m, 2H, Ph-H), 7.64 (m, 1H, Ph-H), 7.70 (d, J=6.4Hz, 1H, Ph-H),
7.87 (m, 1H, Ph-H), 7.97 (m, 1H, Ph-H), 8.15 (d, J=6.4Hz, 2H, Ph-H) .HRMS (ESI) m/z:
Calculated,395.1866,Found,395.1872[M+H]+.
Embodiment 11
1-(furan-2-base)-8-methoxyl group-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 96.5%, molten
Point 149-151 DEG C；1H NMR (400MHZ, CDCl3/TMS), δ 4.00 (s, 3H, OCH3), 6.91 (d, J=2.4Hz, 1H,
Furan-H), 7.47 (m, 2H, 1Ph-H, 1furan-H), 7.56 (m, 3H, Ph-H), 7.64 (q, J=6.0Hz, 1H, Ph-H),
7.87 (m, 2H, Ph-H), 7.97 (m, 1H, Ph-H), 8.83 (d, J=6.4Hz, 1H, furan-H) .HRMS (ESI) m/z:
Calculated,343.1190,Found,343.1200[M+H]+.
Embodiment 12
8-methoxyl group-1-(2,4-Dichlorobenzene base)-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 84.5%,
Fusing point 134-139 DEG C；1H NMR (400MHZ, CDCl3/TMS), δ 4.00 (s, 3H, OCH3), 7.37 (d, J=7.2Hz, 1H,
Ph-H),7.48(s,1H,Ph-H),7.55(m,4H,Ph-H),7.64(m,1H,Ph-H),7.71(s,1H,Ph-H),7.88(m,
2H, Ph-H), 7.98 (t, J=7.2Hz, 2H, Ph-H) .HRMS (ESI) m/z:Calculated, 421.0617, Found,
421.0630[M+H]+.
Embodiment 13
1-(3-chlorphenyl)-8-methoxyl group-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 70.8%, fusing point
149-151℃；1H NMR(400MHZ,CDCl3/TMS),δ4.00(s,3H,OCH3),7.43-7.48(m,3H,Ph-H),7.56
(m, 3H, Ph-H), 7.62 (d, J=6.4Hz, 1H, Ph-H), 7.88 (m, 2H, Ph-H), 7.97 (d, J=6.4Hz, 1H, Ph-
H), 8.02 (d, J=6.4Hz, 1H, Ph-H), 8.12 (s, 1H, Ph-H) .HRMS (ESI) m/z:Calculated, 387.1007,
Found,387.1015[M+H]+.
Embodiment 14
1-(4-fluorophenyl)-8-methoxyl group-4-phenyl-[1,2,4] triazole [4,3-a] quinoxaline, yield 79.7%, fusing point
178-181℃；1H NMR (400MHZ, CDCl3/TMS), δ 4.00 (s, 3H, OCH3), 7.18 (t, J=6.8Hz, 2H, Ph-H),
7.47 (m, 2H, Ph-H), 7.57 (m, 3H, Ph-H), 7.88 (m, 2H, Ph-H), 7.97 (d, J=7.2Hz, 1H, Ph-H), 8.16
(m,2H,Ph-H).HRMS(ESI)m/z:Calculated,371.1307,Found,371.1303[M+H]+.
Embodiment 15
Tolyl-[1,2,4] triazole [4,3-a] quinoxaline between 8-methoxyl group-4-phenyl-1-, yield 58.2%, fusing point
175-179℃；1H NMR(400MHZ,CDCl3/TMS),δ2.45(s,3H,CH3),4.00(s,3H,OCH3),7.44-7.48
(m,3H,Ph-H),7.56(m,4H,Ph-H),7.87(m,2H,Ph-H),7.93-7.98(m,3H,Ph-H).HRMS(ESI)m/
z:Calculated,389.1373,Found,389.1180[M+Na]+.
Embodiment 16 activity of weeding is tested
Subjects: creeping bentgrass, Caulis et Folium Lactucae Sativae.
Test method: complete the filter paper of a diameter 5.6cm in the culture dish of diameter 6cm, add 2 milliliters certain density
Test compounds solution, the sowing seed soaking Semen Brassicae campestris 10 of 6 hours.At 28 ± 1 DEG C, dark culturing measures radicle after 7 days long
Degree.By compound under dark condition, the growth inhibited of crop radicle is come the activity of weeding of detection compound.Test concentrations:
1mM.Each process is in triplicate.Activity graded index: 5 grades: >=80%；4 grades: 60～80%；3 grades: 40～59%；2 grades: 20
～39%；1 grade: 1～20%；0 grade: 0%.
The Herbicide activity data of table 1 embodiment 1-15
Showing from table 1 activity of weeding, 4,7,10,12,13,14 pairs of creeping bentgrasses of embodiment have good activity of weeding, wherein
4,10 pairs of Caulis et Folium Lactucae Sativae of embodiment have activity of weeding.
Claims (10)
1. 1,2,4-triazole derivatives containing methoxyl group benzopyrazines structure, it is characterised in that its structural formula is as shown in (I):
Wherein: R1For phenyl, undecyl, 3-fluorophenyl, 4-amyl group phenyl, 4-nitrobenzophenone, 3-nitrobenzophenone, 4-methoxyl group
Phenyl, 4-isopropyl phenyl, 2-chloropyridine, 4-n-pro-pyl phenyl, 2-furan, 2,4-Dichlorobenzene base, 3-chlorphenyl, 4-fluorobenzene
Base, 3-aminomethyl phenyl.
2. the preparation side of the 1,2,4-triazole derivative containing methoxyl group benzopyrazines structure according to claim 1
Method, it is characterised in that comprise the steps:
1) being solvent at methanol, Raney Ni is under catalysts conditions, and 4-methoxyl group-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 compound as shown in formula III
(III) crude product；
3) by step 2) compound (III) crude product that obtains through washing with alcohol after purification, uses POCl3Make solvent, be heated to reflux bar
Carry out chlorination reaction under part, terminate through TLC monitoring reaction, the post-treated compound (IV) obtained as shown in formula IV, go forward side by side
Row the next step；
4) with ethanol as solvent, by step 3) compound (IV) and the hydrazine hydrate that obtain react (the 7-first shown in acquisition formula (V)
Epoxide-3-phenyl quinoxaline-2-base) hydrazine crude product (V)；
5) by step 4) compound (V) crude product that obtains is after recrystallization purifying, with POCl3Make solvent, with replacement acids
Compound reacts to obtain the 1,2,4-triazole derivative containing methoxyl group benzopyrazines structure shown in formula (I)；
Preparation process is as follows:
The preparation method of 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure the most according to claim 2, its
Be characterised by step 1) in, each material inventory of addition is: 0.1mol 4-methoxyl group ortho-nitraniline, 30-50mL methanol,
The hydrazine hydrate of 70-80mL85%, 0.25～0.45g Raney Ni, preferably 0.1mol 4-methoxyl group ortho-nitraniline, 40mL
Methanol, the hydrazine hydrate of 75mL85%, 0.25～0.45g Raney Ni, Raney Ni is weight in wet base.
The preparation method of 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure the most according to claim 2, its
Be characterised by step 2) in reaction temperature be room temperature, the response time is 30-90min.
The preparation method of 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure the most according to claim 2, its
Be characterised by step 3) in post-processing approach be: be poured slowly into after completion of the reaction in frozen water, separate out a large amount of yellow solid immediately, take out
Filter, washing are dried, and obtain compound (IV).
The preparation method of 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure the most according to claim 2, its
It is characterised by step 4) in, compound (IV) is 1:2.5-3.5, preferably 1:3 with the molar ratio of the hydrazine hydrate of 85%.
The preparation method of 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure the most according to claim 2, its
Being characterised by that compound (V) is 1:1:1.2 with the ratio of the amount of the material of replacing acid compounds, the time of being heated to reflux is 3.5-
4.54h, the ratio of the amount of preferred substance is 1:1:1.2, and the time of being heated to reflux is 4h.
The preparation method of 1,2, the 4-triazole derivatives containing methoxyl group benzopyrazines structure the most according to claim 2, its
It is characterised by step 3) in, extract reaction solution during TLC monitoring, join and frozen water cracks POCl3, then it is extracted with ethyl acetate product
Thing, takes organic layer, with ethyl acetate: petroleum ether=1:3 mixed liquor is as developing solvent, and what monitoring was reacted carries out degree.
9. the 1,2,4-triazole derivative containing methoxyl group benzopyrazines structure according to claim 1 is as herbicide
Application.
10. the 1,2,4-triazole derivative containing methoxyl group benzopyrazines structure as claimed in claim 1 is as herbicide
In preventing and treating creeping bentgrass, the application of Caulis et Folium Lactucae Sativae weeds.
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| CN111423388A (en) * | 2020-04-29 | 2020-07-17 | 浙江工业大学 | 7-methoxy-3-phenylquinoxaline-2 (1H) -one derivative and preparation method and application thereof |
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