CN106234373B - A kind of application of hydrazone compounds of the structure of benzopyrazines containing methyl as fungicide - Google Patents
A kind of application of hydrazone compounds of the structure of benzopyrazines containing methyl as fungicide Download PDFInfo
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- CN106234373B CN106234373B CN201610617529.7A CN201610617529A CN106234373B CN 106234373 B CN106234373 B CN 106234373B CN 201610617529 A CN201610617529 A CN 201610617529A CN 106234373 B CN106234373 B CN 106234373B
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- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
Application the invention discloses a kind of hydrazone compounds of structure of benzopyrazines containing methyl as fungicide.Compound 1 is made with 4- methyl ortho-nitraniline and hydrazine hydrate in it；Compound 1 and BMF, which are acted on, is made compound 2；Compound 3 is made in compound 2 and phosphorus oxychloride reaction；Compound 4 is made in compound 3 and hydration hydrazine reaction；Compound 4 reacts obtained compound (I) with aldehyde compound is replaced.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 antifungal activity, there is good bactericidal effect especially for point spore anthrax bacteria, Strawberry anthracnose bacterium and fructus lycii anthrax bacteria, provide the foundation for novel pesticide research and development.
Description
Technical field
Application the present invention relates to a kind of hydrazone compounds of structure of benzopyrazines containing methyl as fungicide.
Background technique
Heterocycle structure is synthetic drug, the important key factor of the substances such as pesticide, this is because heterocycle is efficient, low toxicity and
It can carry out what the characteristics of diversification replaces was determined.It has become medicine, a research hotspot in the field of pesticide.Hydrazone class
Compound has the extensive bioactivity such as good weeding, desinsection, sterilization, while tying because containing the Asia C=N in its molecular structure
Structure makes it have the coordination mode of stronger coordination ability and multiplicity, can synthesize the new compound of many high activities, and hydrazone
There are also good antitumor and oxidation resistant activity for class compound and its complex, therefore lead in pesticide, medicine, detection and material
There is application in domain.The extensive concern for the person that even more receives pesticide research, is studied more and more deep in terms of New pesticides discovery.Previous generation
It records and has the kind of commercialization the fifties, E.I.Du Pont Company, which reported Benzophenonehydrazones analog derivative at 1973 and has, well to kill
Worm activity, especially has lepidoptera pest high-efficiency activated；The benquinox that Beyer Co., Ltd develops is in prevention and treatment pythium spp and soil fungi
Caused seed and sprout term disease have better effects；Schiff bases and fatty acylhydrazone are right by apparent activity of weeding
Broadleaf weeds and barnyard grass have excellent activity.
Summary of the invention
Application it is an object of the present invention to provide a kind of hydrazone compounds of structure of benzopyrazines containing methyl as fungicide.
Application of the hydrazone compounds of a kind of structure of benzopyrazines containing methyl as fungicide, it is characterised in that contain
The structural formula of the hydrazone compounds of methyl benzopyrazines structure is such as shown in (I):
Wherein: R1It is 3,4,5- trimethoxyphenyls, 2,4- dichlorophenyls, 3- nitrobenzophenone, 2- bromophenyl, 2- hydroxy benzenes
Base, 2- nitrobenzophenone, 2- fluorophenyl, 4- bromophenyl, 4- isopropyl phenyl, 2- methoxyphenyl, 3- chlorphenyl, 4- fluorophenyl,
3,4- Dimethoxyphenyls, 4- aminomethyl phenyl, 2- furans phenyl, methyl.
The hydrazone compounds of the structure of benzopyrazines containing methyl are as the sharp spore anthrax-bacilus of prevention and treatment, strawberry anthrax-bacilus, Chinese holly
The application of the fungicide of Qi anthrax bacteria.
The application, it is characterised in that R1For 2- hydroxy phenyl, 2- bromophenyl, 2,4- dichlorophenyls, 3- chlorphenyl
(B10), 2- furans phenyl, 4- isopropyl phenyl.
The preparation method of the hydrazone compounds of the structure of benzopyrazines containing methyl, it is characterised in that including walking as follows
It is rapid:
1) in organic solvent, 5- methyl ortho-nitraniline and hydration hydrazine reaction are obtained such as formula 1 under the action of Raney Ni
Compound represented 5- methyl ortho-nitraniline；
2) in organic solvent, the 5- methyl ortho-nitraniline that step 1) obtains is reacted under ethyl alcohol effect with MBF
To compound 7- methyl -2- hydroxyl -3- phenyl quinoxaline as shown in Equation 2；
3) the 7- methyl -2- hydroxyl -3- phenyl quinoxaline for obtaining step 2) and phosphorus oxychloride action-reaction are generated such as formula 3
The chloro- 3- phenyl quinoxaline of compound represented 7- methyl -2-；
4) the chloro- 3- phenyl quinoxaline of 7- methyl -2- for obtaining step 3) and hydrazine hydrate action-reaction generate as shown in Equation 4
Compound (7- methyl -3- phenyl quinoxaline -2- base) hydrazine；
5) (7- methyl -3- phenyl quinoxaline -2- base) hydrazine and substitution aldehydes that in organic solvent, step 4) is obtained
It closes object reaction and generates the target hydrazone compounds as shown in formula (I)；
Preparation process is as follows:
The preparation method of the hydrazone compounds of the structure of benzopyrazines containing methyl, it is characterised in that 5- first in step 1)
The amount of the substance of base ortho-nitraniline and the mass ratio of Raney Ni are 1:2.5~4.5, and organic solvent is methanol, volume
Dosage is calculated as 0.3~0.5ml/mmol with the amount of the substance of 5- methyl ortho-nitraniline, and the dosage of 85% hydrazine hydrate is with 5- first
The amount of the substance of base ortho-nitraniline is calculated as 0.7~0.8ml/mmol.
The preparation method of the hydrazone compounds of the structure of benzopyrazines containing methyl, it is characterised in that 4- first in step 2)
The ratio between amount of substance of base o-phenylenediamine and MBF is 1:1.5~3.5.
The preparation method of the hydrazone compounds of the structure of benzopyrazines containing methyl, it is characterised in that organic in step 2)
Solvent is methanol, ethyl alcohol or DMF, and volumetric usage is calculated as 0.9~1.1ml/mmol with the amount of the substance of 4- methyl-o-phenylenediamine.
The preparation method of the hydrazone compounds of the structure of benzopyrazines containing methyl, it is characterised in that trichlorine in step 3)
Oxygen phosphorus volumetric usage is calculated as 0.3~0.5ml/mmol with the amount of the substance of 7- methyl -2- hydroxyl -3- phenyl quinoxaline.
The preparation method of the hydrazone compounds of the structure of benzopyrazines containing methyl, it is characterised in that 7- first in step 4)
The ratio between amount of substance of the chloro- 3- phenyl quinoxaline of base -2- and hydrazine hydrate is 1:1.5~4.5.
The preparation method of the hydrazone compounds of the structure of benzopyrazines containing methyl, it is characterised in that (7- in step 5)
Methyl -3- phenyl quinoxaline -2- base) hydrazine and the ratio between amount of substance of aldehyde compound is replaced to be 1:0.9~1.1.
The preparation method of the hydrazone compounds of the structure of benzopyrazines containing methyl, it is characterised in that organic in step 5)
Solvent is methanol, ethyl alcohol or DMF, and dosage is to replace the amount of the substance of aldehyde compound to be calculated as 7.0~8.0ml/mmol.
Compared with prior art, the beneficial effects are mainly reflected as follows: the present invention provides one kind contain benzopyrazines
The preparation method and application of the hydrazone compounds of structure, raw material is simple and easy to get, and preparation method is simple, convenient post-treatment, produces
Product high income, the compound are especially to prevent and treat sharp spore anthrax-bacilus, strawberry anthrax-bacilus, fructus lycii anthracnose with antibacterial activity
Bacterium has good preventive and therapeutic effect, provides the foundation for the research and development of novel pesticide.
Specific embodiment
The present invention is described further combined with specific embodiments below, but protection scope of the present invention is not limited in
This:
The hydrazone compounds (I) of the structure of benzopyrazines containing methyl of the invention can synthesize in the following manner:
The present invention is described further combined with specific embodiments below, but protection scope of the present invention is not limited in
This:
The hydrazone compounds (I) of the structure containing benzopyrazines of the invention can synthesize in the following manner:
In 250mL single-necked flask, 0.1mol 4- methyl ortho-nitraniline, 40mL methanol, 75mL hydrazine hydrate are sequentially added
(85%), 0.25~0.45Rany Ni (weight in wet base), is heated to reflux, and is tracked with TCL to raw material and is disappeared, is cooled to after reaction
Room temperature, is filtered to remove Rany Ni, and vacuum distillation removes solvent and obtains filbert crystal to get compound as shown in Equation 1 is arrived
14- methyl-o-phenylenediamine.In 250mL single-necked flask, 0.1mol substituted o-phenylenediamine is added, is dissolved with 100mL ethyl alcohol,
MBF is slowly added dropwise again, has yellow solid appearance during dropwise addition, according to substituent R1Variation, the reaction time is different, normal
The lower reaction period of temperature is 30-120min, after fully reacting, is filtered to remove solvent, is flushed three times with ethyl alcohol, is obtained such as 2 institute of formula
The compound 7- methyl -2- hydroxyl -3- phenyl quinoxaline shown.40mLPOCl is added in compound 23Solvent is made, is heated to reflux
Under the conditions of carry out chlorination, with TLC track to raw material disappear, be cooled to room temperature, be poured slowly into 500g ice water after reaction, stand
A large amount of yellow solids are precipitated, filters, washing drying, obtains compound 3 as shown in Equation 3.In 250mL three-necked flask, add
Enter compound 3 and make solvent with 60mL ethyl alcohol, the hydrazine hydrate of 18g (0.3mol) 85% is slowly added dropwise, is warming up to after being added dropwise
Reflux reacts 4-5h, is cooled to room temperature, is poured into 300g ice water after reaction, a large amount of white solids are precipitated immediately, through taking out
Filter, washing and dry, obtained crude product, to obtain compound 4 as shown in Equation 4 by recrystallizing.It is added in 50mL round-bottomed flask
0.377g (0.002mol) hydrazine is added 15mL ethyl alcohol and makees solvent, and 0.002mol is slowly added dropwise under stirring condition and replaces aldehydes chemical combination
Object, raw material dissolve rapidly, then have solid precipitation, are stirred overnight at room temperature, and contact plate monitoring after raw material fully reacting, is filtered, used
The mixed liquor of petroleum ether and ethyl alcohol washs three times, obtains reddish yellow solid powder, i.e., as shown in formula (I) containing benzopyrazines structure
Hydrazone compounds.
The structural formula of embodiment 1~15, particular compound is as shown in table 2, and other synthesis conditions do not change.
Embodiment 1
(E)-(2- (2- (7- methyl -3- phenyl quinoxaline -2- base) hydrazine) methyl) phenol, reddish yellow solid, yield
87.5%, m.p.113-116 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, 355.1553, Found, 355.1572 [M+H]+
Embodiment 2
(E) -3- (2- (2- bromophenyl) hydrazine) -6- methyl -2- phenyl quinoxaline, reddish yellow solid, yield 68.3%,
m.p.80-83℃；1H NMR(400MHz,CDCl3/TMS),δ2.52(S,3H,CH3), 7.26 (q, J=6.0Hz, 1H, Ph-H),
7.38 (t, J=6.0Hz, 2H, Ph-H), 7.57-7.77 (m, 8H, Ph-H), 8.17 (m, 1H, Ph-H) .FTIR υ (cm-1):
687.47,1088.49,1462.76,1610.96,2929.38,2958.79,3063.75.HRMS(ESI)m/z:
Calculated,417.0709,Found,417.0729[M+H]+
Embodiment 3
(E) -6- methyl -3- (2- (3- nitrobenzophenone) hydrazine) -2- phenyl quinoxaline, reddish yellow solid, yield 71.9%,
m.p.172-175℃；1H NMR(400MHz,CDCl3/TMS),δ2.55(S,3H,CH3), 7.23 (d, J=6.8Hz, 1H, Ph-
), H 7.37 (d, J=6.8Hz, 1H, Ph-H), 7.63 (m, 3H, Ph-H), 7.74 (m, 3H, Ph-H), 7.87 (m, 2H, Ph-H),
8.16 (q, J=6.8Hz, 2H, Ph-H), 8.59 (m, 1H, NH), 8.89 (m, 1H ,=CH) .HRMS (ESI) m/z:
Calculated,384.1455,Found,384.1478[M+H]+
Embodiment 4
(E) -3- (2- (3,4- Dimethoxyphenyl) hydrazine) -6- methyl -2- phenyl quinoxaline, reddish yellow solid, yield
81.8%, m.p.105-108 DEG C；1H NMR(400MHz,CDCl3/TMS),δ2.53(S,3H,CH3),4.02(S,3H,OCH3),
4.05(S,3H,OCH3), 7.13 (t, J=5.0Hz, 1H, Ph-H), 7.23 (d, J=2.0Hz, 1H, Ph-H), 7.34 (m, 1H,
), Ph-H 7.51-7.56 (m, 5H, Ph-H), 7.63 (m, 1H, Ph-H), 8.02 (s, 1H, Ph-H), 8.09 (d, J=6.4Hz,
1H, Ph-H), 8.87 (m, 2H, 1NH, 1=CH) .HRMS (ESI) m/z:Calculated, 399.1816, Found, 399.1842
[M+H]+
Embodiment 5
(E) -3- (2- (2- fluorophenyl) hydrazine) -6- methyl -2- phenyl quinoxaline, reddish yellow solid, yield 78.7%,
m.p.139-141℃；1H NMR(400MHz,CDCl3/TMS),δ2.53(S,3H,CH3),7.20(m,1H,Ph-H),7.37(q,
J=8.6Hz, 2H, Ph-H), 7.43 (d, J=8.2Hz, 1H, Ph-H), 7.47 (q, J=7.0Hz, 1H, Ph-H), 7.54-7.59
(m, 2H, Ph-H), 7.72-7.76 (m, 2H, Ph-H), 7.79 (t, J=7.2Hz, 1H, Ph-H), 8.87 (m, 2H, 1NH, 1=
CH).HRMS(ESI)m/z:Calculated,357.1510,Found,357.1513[M+H]+
Embodiment 6
(E) -3- (2- (2,4- dichlorophenyl) hydrazine) -6- methyl -2- phenyl quinoxaline, reddish yellow solid, yield 60.8%,
m.p.141-143℃；1H NMR(400MHz,CDCl3/TMS),δ2.53(S,3H,CH3),7.08-7.46(m,2H,Ph-H),
7.60 (m, 4H, Ph-H), 7.70 (m, 2H, Ph-H), 8.04-8.06 (m, 2H, Ph-H), 8.89 (m, 1H ,=CH) .HRMS
(ESI)m/z:Calculated,407.0825,Found,407.082 9[M+H]+
Embodiment 7
(E) -6- methyl -2- phenyl -3- (2- (2,3,4- trimethoxy) hydrazine) quinoxaline, reddish yellow solid, yield
74.5%, m.p.82-85 DEG C；1H NMR(400MHz,CDCl3/TMS),δ2.54(S,3H,CH3),3.96(s,9H,OCH3),
7.06 (s, 2H, Ph-H), 7.56-8.60 (m, 8H, 7Ph-H, 1=CH) .HRMS (ESI) m/z:Calculated, 429.1921,
Found,429.1926[M+H]+
Embodiment 8
(E) -6- methyl -3- (2- (2- nitrobenzophenone) hydrazine) -2- phenyl quinoxaline, reddish yellow solid, yield 46.0%,
m.p.119-121℃；1H NMR(400MHz,CDCl3/TMS),δ2.54(S,3H,CH3),7.46-7.54(m,5H,Ph-H),
7.68 (t, J=7.5Hz, 1H, Ph-H), 7.71-7.89 (m, 3H, Ph-H), 8.00 (d, J=8.6Hz, 2H, Ph-H), 8.27
(m, 1H, Ph-H), 8.73 (m, 1H, 1=CH) .HRMS (ESI) m/z:Calculated, 384.1455, Found, 384.1456
[M+H]+
Embodiment 9
(E) -3- (2- (4- bromophenyl) hydrazine) -6- methyl -2- phenyl quinoxaline, reddish yellow solid, yield 95.8%,
m.p.139-142℃；1H NMR(400MHz,CDCl3/TMS),δ2.50(S,3H,CH3), 7.45 (d, J=8.6Hz, 2H, Ph-
H),7.55(m,5H,Ph-H),7.63-7.66(m,3H,Ph-H),7.81(m,1H,Ph-H),8.01(s,1H,Ph-H),8.10
(d, J=8.2Hz, 1H, Ph-H), 8.86 (m, 1H ,=CH) .HRMS (ESI) m/z:Calculated, 417.0709, Found,
417.0697[M+H]+
Embodiment 10
(E) -3- (2- (3- chlorphenyl) hydrazine) -6- methyl -2- phenyl quinoxaline, reddish yellow solid, yield 50.0%,
m.p.127-130℃；1H NMR(400MHz,CDCl3/TMS),δ2.52(S,3H,CH3),7.36(m,2H,Ph-H),7.43(d,
J=8.6Hz, 1H, Ph-H), 7.55 (m, 2H, Ph-H), 7.60-7.65 (m, 4H, Ph-H), 7.86 (t, J=10.0Hz, 2H,
), Ph-H 8.03 (s, 1H, Ph-H), 8.10 (d, J=8.2Hz, 1H, Ph-H), 8.86 (m, 1H ,=CH) .HRMS (ESI) m/z:
Calculated,373.1215,Found,373.1211[M+H]+
Embodiment 11
(E) -3- (2- (2- methoxyphenyl) hydrazine) -6 methyl -2- phenyl quinoxalines, reddish yellow solid, yield 86.0%,
m.p.105-108℃；1H NMR(400MHz,CDCl3/TMS),δ2.50(S,3H,CH3),3.68(s,3H,OCH3),7.12(m,
1H, Ph-H), 7.17-7.26 (m, 2H, Ph-H), 7.34 (d, J=8.6Hz, 1H, Ph-H), 7.62 (m, 3H, Ph-H), 7.89
(m, 2H, Ph-H), 8.06 (d, J=8.2Hz, 1H, Ph-H), 8.88 (m, 2H, 1NH, 1=CH) .HRMS (ESI) m/z:
Calculated,369.1710,Found,369.1711[M+H]+
Embodiment 12
(E) -6- methyl -3- (2- (4- aminomethyl phenyl) hydrazine) -2- phenyl quinoxaline, reddish yellow solid, yield 80.7%,
m.p.240-243℃；1H NMR(400MHz,CDCl3/TMS),δ2.52(S,3H,CH3),2.56(s,3H,CH3),7.46(m,
4H, Ph-H), 7.61 (m, 2H, Ph-H), 7.63 (m, 2H, Ph-H), 8.00 (s, 1H, Ph-H), 8.07 (d, J=6.8Hz, 1H,
), Ph-H 8.88 (m, 3H, 1Ph-H, 1NH, 1=CH) .HRMS (ESI) m/z:Calculated, 353.1761, Found,
353.1764[M+H]+
Embodiment 13
(E) -3- (2- (2- (furans -3- base) benzal) hydrazine) -6- methyl -2- phenyl quinoxaline, reddish yellow solid, yield
78.9%, m.p.123-126 DEG C；1H NMR(400MHz,CDCl3/TMS),δ2.55(S,3H,CH3),6.78(m,1H,furan-
), H 7.17 (d, J=3.2Hz, 1H, furan-H), 7.34 (m, 1H, Ph-H), 7.48 (m, 1H, Ph-H), 7.62 (m, 3H, Ph-
), H 7.82 (m, 1H, furan-H), 8.02 (s, 1H, Ph-H), 8.10 (d, J=8.2Hz, 1H, Ph-H), 8.85 (m, 3H, 1Ph-
H, 1NH, 1=CH) .HRMS (ESI) m/z:Calculated, 329.1397, Found, 329.1407 [M+H]+
Embodiment 14
(E) -3- (2- (4- isopropyl phenyl) hydrazine) -6- methyl -2- phenyl quinoxaline, reddish yellow solid, yield 61.8%,
m.p.137-140℃；1H NMR(400MHz,CDCl3/ TMS), δ 1.72 (t, J=7.2Hz, 6H, CH3),2.60(S,3H,
CH3),3.93(m,1H,CH3), 7.50 (d, J=8.4Hz, 1H, Ph-H), 7.59 (m, 4H, Ph-H), 7.98 (s, 1H, Ph-H),
8.00 (s, 1H, Ph-H), 7.62 (m, 3H, Ph-H), 8.10 (m, 1H, Ph-H), 8.84 (m, 2H, 1NH, 1=CH) .HRMS
(ESI)m/z:Calculated,303.1615,Found,303.1605[M-H]-
Embodiment 15
(E) -3- (2- ethylidene hydrazine) -6- methyl -2- phenyl quinoxaline, reddish yellow solid, yield 60.9%, m.p.90-
93℃；1H NMR(400MHz,CDCl3/TMS),δ2.54(S,3H,CH3),2.57(s,3H,CH3),7.48(m,1H,Ph-H),
7.52-7.57 (m, 5H, Ph-H), 7.62 (s, 1H, Ph-H), 7.62 (m, 3H, Ph-H), 7.87 (d, J=6.8Hz, 1H, Ph-
H).HRMS(ESI)m/z:Calculated,275.1302,Found,275.1293[M-H]-
The test of 16 antifungal activity of embodiment
Subjects: sharp spore anthrax-bacilus, strawberry anthrax-bacilus, fructus lycii anthrax bacteria.
Inoculation method: the conidium of each fungal species is gently brushed into lamellae with a L shape glass bar.
Direct bioautography: after waiting tests, the radius size of thin-layer chromatography version is measured.
Antibacterial activity test result is as shown in table 1
The bactericidal activity data of 1 compound B-11-B16 of table
Show compound B-11 5 under the conditions of microtitration to fungi point spore anthrax bacteria, strawberry charcoal from 1 antibacterial activity of table
Subcutaneous ulcer germ and fructus lycii anthrax bacteria have good activity, and compound B-11, B2, B6, B10, B13, B14 have centainly three kinds of targets
Bactericidal activity.
Particular compound structure is as shown in table 2
The specific structure of 2 compound B-11-B15 of table
Claims (3)
1. a kind of hydrazone compounds of structure of benzopyrazines containing methyl are as the sharp spore anthrax-bacilus of prevention and treatment, strawberry anthrax-bacilus, fructus lycii charcoal
The application of the fungicide of subcutaneous ulcer germ, it is characterised in that the structural formula of the hydrazone compounds of the structure of benzopyrazines containing methyl such as (I) institute
Show:
Wherein: R1For 2- hydroxy phenyl, 2- bromophenyl, 2,4- dichlorophenyls, 3- chlorphenyl, 2- furans phenyl, 4- isopropyl phenyl
Or methyl.
2. a kind of sterilization of hydrazone compounds of the structure of benzopyrazines containing methyl as prevention and treatment strawberry anthrax-bacilus, fructus lycii anthrax bacteria
The application of agent, it is characterised in that the structural formula of the hydrazone compounds of the structure of benzopyrazines containing methyl is such as shown in (I):
Wherein: R1For 3,4,5- trimethoxyphenyl.
3. a kind of application of hydrazone compounds of the structure of benzopyrazines containing methyl as the fungicide of prevention and treatment fructus lycii anthrax bacteria,
It is characterized in that the structural formula such as (I) of the hydrazone compounds of the structure of benzopyrazines containing methyl is shown:
Wherein: R1For 3,4- Dimethoxyphenyl or 2- fluorophenyl.
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| CN201610617529.7A CN106234373B (en) | 2016-07-28 | 2016-07-28 | A kind of application of hydrazone compounds of the structure of benzopyrazines containing methyl as fungicide |
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Citations (2)
| 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 |
| CN103224470A (en) * | 2013-05-17 | 2013-07-31 | 南京农业大学 | Preparation method and application of quinoxaline-6-phenylhydrazone derivants |
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Patent Citations (2)
| 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 |
| CN103224470A (en) * | 2013-05-17 | 2013-07-31 | 南京农业大学 | Preparation method and application of quinoxaline-6-phenylhydrazone derivants |
Non-Patent Citations (1)
| Title |
|---|
| Quinoxaline derivatives part II: Synthesis and antimicrobial testing of 1,2,4-triazolo[4,3-a]quinoxalines, 1,2,4-triazino[4,3-a]quinoxalines and 2-pyrazolylquinoxalines;S.A.El-HAWASH, et al;《Pharmazie》;19991231;第54卷;第808页"Scheme 1"部分，第810页Table 1、Table2部分 * |
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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 hydrazone compound containing a methyl benzopyrazine structure as a fungicide Granted publication date: 20190628 License type: Common License Record date: 20230316 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 hydrazone compound containing a methyl benzopyrazine structure as a fungicide Granted publication date: 20190628 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 hydrazone compound containing a methyl benzopyrazine structure as a fungicide Granted publication date: 20190628 License type: Common License Record date: 20230316 |
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