CN106070263B - 5- amino -1H- Bi Zuos [3,4-d]Application of pyrimidine -4 (5H) the -one class compound in preparing anti-plant virus agent - Google Patents
5- amino -1H- Bi Zuos [3,4-d]Application of pyrimidine -4 (5H) the -one class compound in preparing anti-plant virus agent Download PDFInfo
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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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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Abstract
The invention discloses a kind of 5- amino -1H- Bi Zuos [3,4-d]Application of pyrimidine -4 (5H) the -one class compound in preparing anti-plant virus agent.
Description
Technical field
The invention belongs to agriculturals to use antivirotic field, relate in particular to a kind of 5- amino -1H- Bi Zuos [3,4-d]It is phonetic
Application of pyridine -4 (5H) the -one class compound in preparing anti-plant virus agent.
Background technology
Bi Zuo [3,4-d]Pyrimidine -4 (5H) -one has anticancer（Molecules 2014, 19, 3297-3309；Bio. Med. Chem., 2013, 21, 5782-5793；J. Chem. Pharm. Res., 2012, 4, 4097-4106; Bioorg. Med. Chem., 2011, 6808–6817；）, sterilization（J. Het. Chem., 2014, 51, 899-905）, It is anti-inflammatory（Sci. Pharmac., 2013, 81, 393-422）Etc. multiple biological activities, be Medicine research hot fields
One of.As Bi Zuo [3,4-d]5 of pyrimidine -4 (5H) -one are upper containing there are one when amino（I.e.：5- amino -1H- Bi Zuos [3,4-d]
Pyrimidine -4 (5H) -one）, due to the modifiability of amino and the characteristic of its reaction, often as the weight of further modification transformation
Want intermediate, amino is more commonly used decorating site.Therefore, 5- amino -1H- Bi Zuos [3,4-d]Pyrimidine -4 (5H) -one is general
In the case of be used as intermediate use.So far, it is reported 5- amino -1H- Bi Zuos [ there are no any;3,4-d]Pyrimidine -4
(5H) -one class compound is as anti-plant virus agent application.
Invention content
The purpose of the present invention is to provide a kind of 5- amino -1H- Bi Zuos [3,4-d]Pyrimidine -4 (5H) -one class compound
Application in preparing anti-plant virus agent.
A kind of 5- amino -1H- Bi Zuos [3,4-d]Pyrimidine -4 (5H) -one class compound is preparing resisting tobacco mosaic virus, horse
Bell potato Y virus, potato virus X, potato virus S, marmor solani, cucumber mosaic virus, tomato virus disease, capsicum disease
Application in the plant virus agents such as viral disease, Virus Diseases of Rice.
Application especially in resisting tobacco mosaic virus, cucumber mosaic virus.
5- amino -1H- Bi Zuos the [ of the present invention;3,4-d]Pyrimidine -4 (5H) -one makees the application in anti-plant virus agent, changes
Object structure is closed as shown in general formula I：
In formula, R1Selected from H, C1-C3Alkyl, R2Selected from methyl, ethyl, tertiary butyl, phenyl, substituted-phenyl, heteroaromatic
Base；R3It can be selected from H, the alkyl of C1-C3.
Further, in the compound described in general formula I, R1Selected from H ,-CH3；R2Selected from methyl, ethyl, tertiary butyl, phenyl,
Aromatic heterocyclic；R3It can be selected from H ,-CH3、-CH2CH3.
Further, in the compound described in general formula I, more preferred substituent group is：R1Selected from H ,-CH3, R2It is selected from
Methyl, ethyl, tertiary butyl, phenyl, 2- chloropyridine bases；R3It can be selected from H ,-CH3。
The general formula I of preferred compound is as follows:
The logical compound of formula I of the present invention can be prepared in accordance with the following methods.Specifically it is referred to document
[Tetrahedron, 1987,43 (18), 4195-202； Liebigs Annalen der Chemie 1985, (9), 1910-1916]It is prepared by the method.In reaction equation, the substitution of intermediate and compound is based on above-mentioned identical, reacts
Cheng Wei：
Synthesized obtained 5- amino -1H- Bi Zuos [3,4-d]Pyrimidine -4 (5H) -one class compound nuclear magnetic data is as follows：
Compound Ia：1H NMR (500 MHz, CDCl3 ) δ 8.29 (s, 1H), 8.15 (s, 1H), 3.96
(s, 3H), 2.31 (s, 2H); 13C NMR 13C NMR (125 MHz, CDCl3) δ 158.25, 145.89,
144.50, 136.77, 87.06, 37.40.
Compound Ib：1H NMR (500 MHz, CDCl3) 8.30 (s, 1H), 3.93 (s, 3H), 2.45 (s,
2H), 1.92 (s, 3H); 13C NMR 13C NMR (125 MHz, CDCl3 ) δ 161.24, 160.13, 148.91,
136.77, 88.46, 37.40, 19.78.
Compound Ic：1H NMR (500 MHz, CDCl3)δ 4.07 (s, 3H), 2.42 (s, 2H), 1.98 (s,
3H), 1.92 (s, 3H).; 13C NMR (125 MHz, CDCl3 )δ 160.09, 158.04, 149.86, 147.59,
106.30, 38.34, 19.78, 14.76.
Compound Id：1H NMR (500 MHz, CDCl3)δ8.15 (s, 1H), 4.07 (s, 3H), 2.33
(brs, 2H), 1.98 (s, 3H); 13C NMR (125 MHz, CDCl3 )δ 160.09, 158.04, 149.86,
147.59, 106.30, 38.34, 19.78, 14.76.
Compound Ie：1H NMR (500 MHz, CDCl3) δ 8.42 – 8.34 (m, 2H), 8.22 (s, 1H),
8.15 (s, 1H), 7.94 – 7.76 (m, 3H); 13C NMR (125 MHz, , CDCl3) δ 158.25,
151.62, 141.48, 141.17, 140.69, 129.30, 129.07, 125.47, 86.29.
Compound If：1H NMR (500 MHz, CDCl3) δ8.39 (dt, J = 4.6, 2.3 Hz, 1H), 8.38
(s, 1H), 7.85 (d, J = 40.0 Hz, 3H), 2.46 (s, 2H), 1.98 (s, 3H), 1.92 (s,
3H).; 13C NMR (125 MHz, , CDCl3) δδ 160.09, 155.54, 152.70, 151.66, 140.81,
128.97, 128.97, 125.03, 108.35, 19.78, 14.76.
Compound Ig per：1H NMR (500 MHz, CDCl3) δ 8.43 (d, J = 1.2 Hz, 1H), 8.37 (d,J = 1.3 Hz, 1H), 8.22 (s, 1H), 7.89 (t, J = 7.4 Hz, 2H), 7.84 – 7.78 (m, 1H),
2.45 (s, 2H), 1.92 (s, 3H); 13C NMR (125 MHz, CDCl3) δ161.24, 158.21, 153.08,
141.17, 140.69, 129.30, 129.07, 125.47, 82.20, 19.78.
Compound Ih：1H NMR (500 MHz, CDCl3) δ8.38 (s, 1H), 8.37 (d, J = 1.3 Hz,
1H), 8.15 (s, 1H), 7.89 (s, 2H), 7.81 (s, 1H), 2.37 (s, 2H), 1.98 (s, 3H).;13C NMR (125 MHz, CDCl3) δ160.45, 152.70, 152.14, 140.81, 140.33, 128.97,
128.97, 125.03, 104.75, 14.76.
Compound Ii：1H NMR (500 MHz, CDCl3) δ 8.30 (s, 2H), 8.15 (s, 2H), 3.97
(q, J = 12.6 Hz, 4H), 2.31 (brs, 4H), 1.29 (s, 3H); 13C NMR (125 MHz, CDCl3) δ
158.25, 149.04, 144.22, 137.74, 90.00, 46.32, 12.41.
Compound Ij：1H NMR (500 MHz, CDCl3) δ 3.97 (q, J = 12.6 Hz, 2H), 2.42 (d,J = 2.8 Hz, 2H), 1.98 (s, 3H), 1.92 (s, 3H), 1.29 (t, J = 12.6 Hz, 3H); 13C
NMR (125 MHz, CDCl3) δ 160.09, 158.60, 152.65, 150.68, 107.82, 47.06, 19.78,
14.76, 12.45.
Compound Ik：1H NMR (500 MHz, CDCl3) δ 8.33 (s, 1H), 3.97 (s, 2H), 2.41
(d, J = 2.5 Hz, 2H), 1.92 (s, 3H), 1.29 (s, 3H).; 13C NMR (125 MHz, CDCl3) δ
161.24, 160.82, 149.91, 137.74, 91.40, 46.32, 19.78, 12.44.
Compound Il：1H NMR (500 MHz, CDCl3) δ 8.15 (s, 1H), 3.97 (s, 2H), 2.33
(d, J = 1.5 Hz, 2H), 1.98 (s, 3H), 1.29 (s, 3H); 13C NMR (125 MHz, CDCl3) δ
160.45, 152.80, 150.68, 143.61, 104.89, 47.06, 14.76, 12.47.
Compound Im：1H NMR (500 MHz, CDCl3) δ 8.94 (dd, J = 7.5, 1.4 Hz, 1H),
8.15 (s, 1H), 8.05 (s, 1H), 7.85 (t, J = 7.5 Hz, 1H), 7.20 (dd, J = 7.4, 1.5
Hz, 1H); 13C NMR (125 MHz, CDCl3) δ158.25, 156.46, 150.81, 148.82, 145.99,
141.48, 139.93, 128.06, 124.28, 99.76.
Compound In：1H NMR (500 MHz, CDCl3) δ 8.92 (dd, J = 15.0, 2.9 Hz, 1H),
7.85 (t, J = 15.0 Hz, 1H), 7.18 (dd, J = 15.0, 2.9 Hz, 1H), 2.46 (s, 2H),
1.97 (s, 3H), 1.95 (s, 3H); 13C NMR (125 MHz, CDCl3) δ 160.09, 155.54, 154.71,
153.62, 149.84, 148.96, 139.18, 127.96, 125.46, 102.54, 19.78, 14.76.
Compound Io：1H NMR (500 MHz, CDCl3) δ 8.91 (dd, J = 15.0, 2.9 Hz, 1H),
8.03 (s, 1H), 7.82 (t, J = 15.0 Hz, 1H), 7.19 (dd, J = 14.9, 3.0 Hz, 1H),
2.42 (s, 2H), 1.91 (s, 3H); 13C NMR (125 MHz, CDCl3) δ 161.24, 158.21, 156.46,
150.52, 148.82, 145.99, 139.93, 128.06, 124.28, 92.47, 19.78.
Compound Ip：1H NMR (500 MHz, CDCl3) δ 8.92 (dd, J = 14.9, 3.0 Hz, 1H),
8.13 (s, 1H), 7.81 (t, J = 14.9 Hz, 1H), 7.16 (dd, J = 14.9, 3.0 Hz, 1H),
2.34 (s, 2H), 1.98 (s, 3H).; 13C NMR (125 MHz, CDCl3) δ 160.45, 154.71,
153.62, 148.96, 148.31, 140.33, 139.18, 127.96, 125.46, 101.56, 14.76.
Compound Iq：1H NMR (500 MHz, CDCl3) δ 8.32 (s, 1H), 8.15 (s, 1H), 2.31
(s, 2H), 1.20 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 158.22, 145.41, 145.24,
141.43, 93.27, 60.29, 28.13.
Compound Ir：1H NMR (500 MHz, CDCl3) δ 2.42 (s, 2H), 1.98 (s, 3H), 1.92
(s, 3H), 1.20 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 160.12, 159.74, 157.21,
147.05, 106.54, 61.12, 28.12, 19.38, 14.76.
Compound Is：1H NMR (500 MHz, CDCl3) δ 8.32 (s, 1H), 2.41 (s, 2H), 1.92
(s, 3H), 1.20 (s, 9H).; 13C NMR (125 MHz, CDCl3); 13C NMR (125 MHz, CDCl3) δ
160.21, 159.73, 157.24, 147.38, 106.25, 61.12, 28.11, 19.72, 14.73.
Compound It：1H NMR (500 MHz, CDCl3) δ 8.15 (s, 1H), 2.33 (s, 2H), 1.98
(s, 3H), 1.20 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 160.46, 157.22, 148.04,
144.32, 106.00, 61.12, 28.12,
Plant virus inhibitor prepared by the compound of the present invention, is mainly used for including tobacco, cucumber, tomato, capsicum, water
Rice, potatoes and other crops, quenchable virus include tobacco mosaic virus (TMV), marmor upsilon, potato virus X, potato S
Virus, marmor solani, cucumber mosaic virus, tomato virus disease, pepper virus disease, Virus Diseases of Rice etc..
Specific implementation mode
With resisting tobacco mosaic virus（Tobacco Mosaic Virus, TMV）And Cucumber Mosaic Virus（CNV）Activity
For, but do not limit the application that the compounds of this invention resists other viruses.
Embodiment 1：To tobacco mosaic disease（TMV）Live body protective effect
The Nicotiana glutinosa for choosing the growing way consistent 5-6 leaves phase gently spreads medicament with writing brush in Zuo Banye, and right half leaf spreads correspondence
The solvent of dosage compares.The moisturizing culture in illumination box controls 23 ± 1 oC of temperature, after illumination 10000 Lux, 12 h
TMV virus liquids are diluted to suitable concentration with phosphate buffer, with the artificial frictional inoculation of spread pen on the blade sprinkled with diamond dust,
Full leaf virus inoculation, after natural drying clear water rinse blade.The then moisturizing culture in illumination box controls temperature 23 ± 1
OC, 10000 Lux of illumination.3 plants, every plant 3 are set per chemicals treatment-4 leaves.3 repetitions are carried out per medicament as stated above.
As a result investigation and analysis：Reference literature（Fan Z.J.;Et al.J.Agric.Food Chem., 2010,58 (5): 2630-2636 and Zuo X.;Et al.J.Agric. Food Chem., 2010,58 (5):2755-2762）Deng described side
Method carries out compound and evaluates the protection of tobacco mosaic virus (TMV).When apparent withered spot is presented on half leaf of blank control, about testing
It can be investigated after 2-3 d, record the withered spot number of half leaf of left and right of every leaf respectively, go out test compound to tobacco by following calculation
The inhibiting rate of mosaic virus, i.e. relative efficacy.
Y=(C-A)∕C ×100%
Wherein：Y is compound to the inhibiting rate to tobacco mosaic virus (TMV)；
C is control group (right half leaf) withered spot number, unit：It is a；
A is compound processing group (Zuo Banye) withered spot number, unit：It is a.
Control group (right half leaf) withered spot number and compound processing group (Zuo Banye) withered spot number can join to be repeated with each group
Average or each group repeat withered spot sum.Each processing be with oneself the other half as a contrast.When blank control
Apparent withered spot is presented on half leaf, can about be investigated after testing 2-3 d, records the withered spot number of half leaf of left and right of every leaf respectively,
Go out inhibiting rate of the test compound to tobacco mosaic virus (TMV), i.e. relative efficacy by following calculation.
Y=(C-A)∕C ×100%
Wherein：Y is compound to the inhibiting rate to tobacco mosaic virus (TMV)；
C is control group (right half leaf) withered spot number, unit：It is a；
A is compound processing group (Zuo Banye) withered spot number, unit：It is a.
Control group (right half leaf) withered spot number and compound processing group (Zuo Banye) withered spot number can join to be repeated with each group
Average or each group repeat withered spot sum.Each processing be with oneself the other half as a contrast.
By test：Under the concentration of 500 mg/L, compound Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Im, In, Io
68%-90% is reached to the protection of tobacco live body.
Embodiment 2：To tobacco mosaic disease（TMV）The passivation of virion
The Nicotiana glutinosa for choosing the growing way consistent 5-6 leaf phases, 6 × 10 are diluted to phosphate buffer by TMV virus liquids-3 mg
Medicament is mixed 30 min of passivation with isometric viral juice, with the artificial frictional inoculation of spread pen in sprinkled with diamond dust by ∕ mL
Zuo Banye, the solvent of matched doses and viral right half leaf of juice combined inoculation, are rinsed with clear water after natural drying.Then in illumination
Moisturizing culture in incubator controls 23 ± 1 oC of temperature, the number for generating withered spot is observed and recorded after illumination 10000 Lux, 2-3d
Mesh.3 plants, every plant 3 are set per chemicals treatment-4 leaves.3 repetitions are carried out per medicament as stated above.
As a result investigation and analysis：Reference literature（Fan Z.J.;Et al.J.Agric.Food Chem., 2010,58 (5): 2630-2636 and Zuo X.;Et al.J.Agric. Food Chem., 2010,58 (5):2755-2762）Deng described side
Method carries out compound and evaluates the passivation of tobacco mosaic virus (TMV).When apparent withered spot is presented on half leaf of blank control, about exist
It can be investigated after experiment 2-3 d, record the withered spot number of half leaf of left and right of every leaf respectively, go out test compound pair by following calculation
The inhibiting rate of tobacco mosaic virus (TMV), i.e. relative efficacy.
Y=(C-A)∕C ×100%
Wherein：Y is compound to the inhibiting rate to tobacco mosaic virus (TMV)；
C is control group (right half leaf) withered spot number, unit：It is a；
A is compound processing group (Zuo Banye) withered spot number, unit：It is a.
Control group (right half leaf) withered spot number and compound processing group (Zuo Banye) withered spot number can join to be repeated with each group
Average or each group repeat withered spot sum.Each processing be with oneself the other half as a contrast.
By test：Under the concentration of 500 mg/L, compound Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Im, In, Io, It
85% or more is reached to TMV passivation activity.
Embodiment 3：To tobacco mosaic disease（TMV）Therapeutic effect
TMV virus liquids, suitable concentration is diluted to phosphate buffer by the Nicotiana glutinosa for the 5-6 leaf phases for selecting growing way consistent,
Full leaf sprinkles evenly diamond dust, with spread pen full leaf virus inoculation, is rinsed after natural drying with clear water.After blade is dry, used in Zuo Banye
Writing brush spreads medicament, and the solvent that right half leaf spreads matched doses compares.The then moisturizing culture in illumination box, control temperature
23 ± 1 oC are spent, the number for generating withered spot is observed and recorded after illumination 10000 Lux, 2-3 d.3 plants, every plant are set per chemicals treatment
3-4 leaves.3 repetitions are carried out per medicament as stated above.
As a result investigation and analysis：Reference literature（Fan Z.J.;Et al.J.Agric.Food Chem., 2010,58 (5): 2630-2636 and Zuo X.;Et al. J.Agric. Food Chem., 2010,58 (5):2755-2762）Deng described in
Method carries out compound and evaluates the therapeutic effect of tobacco mosaic virus (TMV).It is apparent withered when being presented on half leaf of blank control
Spot can about be investigated after testing 2-3 d, record the withered spot number of half leaf of left and right of every leaf respectively, go out for examination by following calculation
Compound is to the inhibiting rate of tobacco mosaic virus (TMV), i.e. relative efficacy.
Y=(C-A) ∕ C ×100%
Wherein：Y is compound to the inhibiting rate to tobacco mosaic virus (TMV)；
C is control group (right half leaf) withered spot number, unit：It is a；
A is compound processing group (Zuo Banye) withered spot number, unit：It is a.
Control group (right half leaf) withered spot number and compound processing group (Zuo Banye) withered spot number can join to be repeated with each group
Average or each group repeat withered spot sum.Each processing be with oneself the other half as a contrast.
After tested：Under the concentration of 500 mg/L, compound Ia, Ib, Ic, Id, Ie, Im, In, Io, Iq, Is, It is to TMV
Therapeutic activity reaches 54-70%.
Embodiment 4：Anti cucumber mosaic virus activity（Protection activity）
Using document（Agricultural University Of South China's journal, 1995,16: 74-79）Described half leaf withered spot method, to being closed
At compound carried out anti-CMV biological activity tests.
The consistent Chenopodium amaranticolor of growing way is chosen, gently spreads medicament in Zuo Banye with writing brush, right half leaf spreads aqua sterilisa and opposes
According to virus inoculation after 24 hours.Viral juice is dipped with spread pen（A concentration of 6 × 10-3 mg / mL）, on blade face（Full leaf）Edge
Its artificial frictional inoculation in offshoot direction is on the blade sprinkled with diamond dust, and the inoculation dynamics of left and right blade is consistent as possible, leaf
It is supported with smooth plank below piece.After virus liquid is dry, the diamond dust above blade is rinsed out with flowing water.3 are set per chemicals treatment
Plant is then placed on moisturizing culture in illumination box by strain, every plant of 5-6 piece leaf, controls 23 ± 1 °C of temperature, illumination
The number for generating withered spot is observed and recorded after 10000 Lux, 6-7 d.3 repetitions are carried out per medicament as stated above, are calculated
Inhibiting rate.
Partial test result is as follows：
By test：Under the concentration of 500 mg/L, compound Ia, Ic, Id, Ie, If, Im, In, Io, Ir protect CMV
Activity reaches 60-88%.
Embodiment 5：Anti cucumber mosaic virus live body therapeutic activity
The consistent Chenopodium amaranticolor of growing way is chosen, first dips virus liquid with spread pen（A concentration of 6 × 10-3 mg / mL）, on blade face
（Full leaf）Along its artificial frictional inoculation in offshoot direction on the blade sprinkled with diamond dust, the inoculation dynamics of left and right blade is kept as possible
Unanimously, it is supported with smooth plank below blade.After virus liquid is dry, the diamond dust above blade is rinsed out with flowing water.Wait for blade
After dry, medicament is spread in Zuo Banye, right half leaf spreads aqua sterilisa and compares.3 plants are set per chemicals treatment, every plant of 5-6 piece leaf,
Plant is then placed on moisturizing culture in illumination box, controls 23 ± 1 °C of temperature, after illumination 10000 Lux, 6-7 d
Observe and record the number for generating withered spot.3 repetitions are carried out per medicament as stated above, calculate inhibiting rate.
By test：Under the concentration of 500 mg/L, compound Ib, Ic, Id, Ie, If, In, Io, Ip, Ir control CMV
It treats activity and reaches 50-72 %.
Embodiment 6：The live body passivation that medicament infects CMV
Medicament is mixed into 30 min of passivation with isometric viral juice, the mixed liquor of medicament and virus is dipped with spread pen,
Artificial frictional inoculation is supported below blade with smooth plank on the left half of blade of the blade sprinkled with diamond dust.Aqua sterilisa and disease
Right half leaf of venom liquid combined inoculation.3 plants are set per chemicals treatment, plant is then placed on illumination box by every plant of 5-6 piece leaf
Middle moisturizing culture controls 23 ± 1 °C of temperature, the number for generating withered spot is observed and recorded after illumination 10000 Lux, 6-7 d.
3 repetitions are carried out per medicament as stated above, calculate inhibiting rate.
Test result shows：Under the concentration of 500 mg/L, compound Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ip,
Ir, Is, It reach 82% or more to CMV therapeutic activities.
The above described is only a preferred embodiment of the present invention, being not intended to limit the present invention in any form, appoint
What is simply repaiied to any made by above example according to the technical essence of the invention without departing from technical solution of the present invention content
Change, equivalent variations and modification, in the range of still falling within technical solution of the present invention.
Claims (3)
1. a kind of 5- amino -1H- Bi Zuos [3,4-d]Pyrimidine -4 (5H) -one class compound answering in preparing anti-plant virus agent
With the 5- amino -1H- Bi Zuos [3,4-d]Pyrimidine -4 (5H) -one class compound is：
2. 5- amino -1H- Bi Zuos [ as described in claim 1;3,4-d]Pyrimidine -4 (5H) -one class compound is preparing anti-tobacco
Mosaic virus, marmor upsilon, potato virus X, potato virus S, marmor solani, cucumber mosaic virus, tomato disease
Viral disease, pepper virus disease, Virus Diseases of Rice plant virus agent in application.
3. 5- amino -1H- Bi Zuos [ as claimed in claim 1 or 2;3,4-d]Pyrimidine -4 (5H) -one class compound is preparing anti-cigarette
Showy flowers of herbaceous plants mosaic virus, cucumber mosaic virus plant virus agent in application.
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| CN103880836B (en) * | 2014-04-04 | 2016-07-06 | 贵州大学 | 1-replaces-5-amino-4-pyrazoles connection 1,3,4-diazole thioether or connection 1,3,4-diazole sulfone derivatives and application thereof |
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