CN108863935A - A kind of amides compound containing pyrazole ring is preparing the application in herbicide - Google Patents
A kind of amides compound containing pyrazole ring is preparing the application in herbicide Download PDFInfo
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- CN108863935A CN108863935A CN201810997254.3A CN201810997254A CN108863935A CN 108863935 A CN108863935 A CN 108863935A CN 201810997254 A CN201810997254 A CN 201810997254A CN 108863935 A CN108863935 A CN 108863935A
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- trifluoromethyl
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- 0 CC(C1)C(NC(NNC(CNC(c2c[n](C)cc2C(F)(F)F)=O)=*)=O)=CC=C1Cl Chemical compound CC(C1)C(NC(NNC(CNC(c2c[n](C)cc2C(F)(F)F)=O)=*)=O)=CC=C1Cl 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
Abstract
The present invention relates to a kind of amides compounds containing pyrazole ring to prepare the application in herbicide.It using romaine lettuce (Lettuce), bent grass (Agrostis) seed as subjects, before bioassay, the surface sterilizing that seed uses the Chlorox solution of 5-10% to carry out 10 minutes, cleaning down then is carried out with the deionized water of Millipore system, is then air-dried in gnotobasis.Sample treatment：All samples use acetone as solvent, and configuration concentration is the solution of 1 mM, by bioassay, show that the compound has preferable activity of weeding, provide the foundation for the research and development of novel pesticide.
Description
Technical field
The present invention relates to a kind of novel amides compound containing pyrazole ring, that is, 1- methyl-N- (2- (2- (carbamyl) acyls
Diazanyl) -2- oxoethyl) -3- Trifluoromethyl-1 H- pyrazole-4-carboxamide derivatives are preparing the application in herbicide.
Background technique
In recent decades, pesticide industry enters the epoch of rapid development, and a feature the most outstanding is exactly jeterocyclic chemistry
Close object extensive application so that pesticide is big from toxicity, side effect is high, high residue old times turns to development for ultra high efficiency, without public affairs
In harmful, environmental-friendly pesticides application new era, heterocyclic compound species are extensive, a variety of systems including nitrogenous, oxygen, sulphur etc.
Column, but wherein also belong to nitrogen-containing heterocycle class using weight is higher in pesticide.Make a general survey of last century end so far, the jeterocyclic chemistry of new listing
It closes object and contains nitrogen, such as sulfonylurea herbicide tribenuron-methyl (Tribenuron methyl), azoles fungicide triazolone
(Triadimefon), Acaricide Fenpyroximate (Fenpyroximate), anabasine insecticide Diacloden (Thiamethoxam)
Deng, it can be seen that, no matter heterocycle compound in weeding, sterilization or in desinsection, mite killing all has very good effect, wherein again
Number nitrogen-containing hetero cyclics are the most prominent.
Instantly the exploitation of heterocycle noval chemical compound is the emphasis of noval chemical compound research, and pyrazole derivatives are as heterocyclic compound
In an important class in new drug development field be even more that there is critical role.Due to pyrazole compound show it is efficient, low
Poison and the characteristics of structure diversity, the pesticide species of many novel, efficient, environment amenable pyrazole derivatives also meet the tendency of and
It is raw, but being widely used with such medicament, since action site is single, resistance problem is also increasingly prominent, and germ insect pest is
Gradually these drugs are produced with different degrees of resistance, therefore the pyrazoles pesticide species for developing novel structure increasingly show
One of its necessity and urgency, and the hot spot studied at present.
Summary of the invention
The object of the present invention is to provide a kind of amides compounds containing pyrazole ring to prepare the application in herbicide.
A kind of amides compound containing pyrazole ring is preparing the application in herbicide, it is characterised in that its structure
Shown in formula such as formula (I)：
In formula (I)：R is phenyl or substituted-phenyl, the substituent group of the substituted-phenyl be halogen, 2- perfluoro propyl, cyano,
Methyl, nitro.
A kind of described 1- methyl-N- (2- (2- (carbamyl) hydrazide group) -2- the oxoethyl) -3- Trifluoromethyl-1 H-
Application of the pyrazole-4-carboxamide derivatives in the herbicide of preparation prevention and treatment romaine lettuce and bent grass, it is characterised in that its structural formula
As shown in formula (I)：
In formula (I)：R is phenyl or substituted-phenyl, the substituent group of the substituted-phenyl be halogen, 2- perfluoro propyl, cyano,
Methyl, nitro.
The application, it is characterised in that R is one of following in formula (I)：Phenyl, 2,3- dichlorophenyls, the chloro- 2- fluorobenzene of 4-
Base, 4- (2- perfluoro propyl) phenyl, 2- cyano-phenyl, 2- methyl -4- nitrobenzophenone.
The beneficial effects are mainly reflected as follows：The present invention provides a kind of 1- methyl-N- (2- (2- (carbamyl)
Hydrazide group) -2- oxoethyl) -3- Trifluoromethyl-1 H- pyrazole-4-carboxamide analog derivative has preferable activity of weeding, and it is special
It is not to have preferable inhibition to romaine lettuce and bent grass, such compound is new agriculture as the noval chemical compound with activity of weeding
The research and development of medicine provide the foundation.
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：
1 1- methyl-N- of embodiment (2- oxo -2- (2- (phenylcarbamoyl) diazanyl) ethyl) -3- (fluoroform
Base) -1H- pyrazole-4-carboxamide preparation
(1) synthesis of ethyl (1- methyl -3- (trifluoromethyl) -1H- pyrazoles -4- carbonyl) glycine ethyl ester (II)：
1- methyl -3- Trifluoromethyl-1 H- pyrazoles -4- acyl chlorides (1.06g, 5mmol) is added to (20ml) methylene chloride
In, it is slowly added to ethyl aminoacetate (1.13g, 11mmol) under ice bath, triethylamine (1.52g, 15mmol) then is added, room temperature
Reaction was completed after reaction 3h, methylene chloride and water 1:1 (V) system extracts three times, and concentration dichloromethane layer obtains white solid, obtains formula
(II) ethyl shown in (1- methyl -3- (trifluoromethyl) -1H- pyrazoles -4- carbonyl) glycine ethyl ester.
(2) conjunction of N- (2- diazanyl -2- oxoethyl) -1- methyl -3- (trifluoromethyl) -1H- pyrazole-4-carboxamide (III)
At：
By ethyl shown in formula (II) (1- methyl -3- (trifluoromethyl) -1H- pyrazoles -4- carbonyl) glycine ethyl ester (1.68g,
5mmol) with 80% hydrazine hydrate (0.94g, 15mmol) back flow reaction 4h, TLC (EA:PE=2:1) it tracks, depressurizes after the reaction was completed
Solid is precipitated in distillation, and then plus water filters to obtain translucent solid, and 75% ethyl alcohol recrystallization obtains N- (2- diazanyl-shown in formula (III)
2- oxoethyl) -1- methyl -3- (trifluoromethyl) -1H- pyrazole-4-carboxamide.
(3) 1- methyl-N- (2- (2- (carbamyl) hydrazide group) -2- oxoethyl) -3- Trifluoromethyl-1 H- pyrazoles -4-
The synthesis of carboxamides derivatives derivative formula：
By N- shown in formula (III) (2- diazanyl -2- oxoethyl) -1- methyl -3- (trifluoromethyl) -1H- pyrazoles -4- formyl
Amine is added in methylene chloride, with phenyl isocyanate with molar ratio 1:1.1 feed intake, and are stirred at room temperature, reaction overnight, TLC (EA/PE
=2/1 (V)) tracking, it is pure to cross column for vacuum distillation removal solvent, petroleum ether elution, 75% ethyl alcohol recrystallization after complete reaction
Change, 1- methyl-N- (2- oxo -2- (2- (phenylcarbamoyl) diazanyl) ethyl)-shown in target compounds of formula (I -1) is made
3- (trifluoromethyl) -1H- pyrazole-4-carboxamide, yield 83%, m.p.161-162 DEG C, 1- methyl-N- (2- shown in formula (I -1)
Oxo -2- (2- (phenylcarbamoyl) diazanyl) ethyl) -3- (trifluoromethyl) -1H- pyrazole-4-carboxamide structural formula is as follows：
1- methyl-N- (2- oxo -2- (2- (phenylcarbamoyl) diazanyl) ethyl) -3- (trifluoromethyl) -1H- pyrrole
Azoles -4- formamide：1H NMR(500MHz,d-DMSO)δ:3.88 (d, J=6.0Hz, 2H, CH2),3.96(s,3H,CH3),6.96
(t, J=7.5Hz, 1H, Ph), 7.24 (t, J=8.5Hz, 2H, Ph), 7.50 (d, J=7.5Hz, 2H, Ph), 8.19 (s, 1H,
NH),8.39(s,1H,CH),8.57(s,1H,NH),8.67(s,1H,NH),9.94(s,1H,NH).
Embodiment 2N- (2- (2- (2,3- dichlorophenyl carbamyl) diazanyl) -2- oxoethyl) -1- methyl -3- (trifluoro
Methyl) -1H- pyrazole-4-carboxamide preparation
(1) synthesis of ethyl (1- methyl -3- (trifluoromethyl) -1H- pyrazoles -4- carbonyl) glycine ethyl ester (II)：
1- methyl -3- Trifluoromethyl-1 H- pyrazoles -4- acyl chlorides (1.06g, 5mmol) is added to (20ml) methylene chloride
In, it is slowly added to ethyl aminoacetate (1.13g, 11mmol) under ice bath, triethylamine (1.52g, 15mmol) then is added, room temperature
Reaction was completed after reaction 3h, methylene chloride and water 1:1 (V) system extracts three times, and concentration dichloromethane layer obtains white solid, obtains formula
(II) ethyl shown in (1- methyl -3- (trifluoromethyl) -1H- pyrazoles -4- carbonyl) glycine ethyl ester.
(2) conjunction of N- (2- diazanyl -2- oxoethyl) -1- methyl -3- (trifluoromethyl) -1H- pyrazole-4-carboxamide (III)
At：
By ethyl shown in formula (II) (1- methyl -3- (trifluoromethyl) -1H- pyrazoles -4- carbonyl) glycine ethyl ester (1.68g,
5mmol) with 80% hydrazine hydrate (0.94g, 15mmol) back flow reaction 4h, TLC (EA:PE=2:1) it tracks, depressurizes after the reaction was completed
Solid is precipitated in distillation, and then plus water filters to obtain translucent solid, and 75% ethyl alcohol recrystallization obtains N- (2- diazanyl-shown in formula (III)
2- oxoethyl) -1- methyl -3- (trifluoromethyl) -1H- pyrazole-4-carboxamide.
(3) 1- methyl-N- (2- ((1- (methylamino) vinyl) amino) ethyl) -3- Trifluoromethyl-1 H- pyrazoles -4-
The synthesis of carboxamides derivatives formula：
By N- shown in formula (III) (2- diazanyl -2- oxoethyl) -1- methyl -3- (trifluoromethyl) -1H- pyrazoles -4- formyl
Amine is added in methylene chloride, with 2,3- dichlorophenyl isocyanate with molar ratio 1:1.1 feed intake, and are stirred at room temperature, reaction overnight,
TLC (EA/PE=2/1 (V)) tracking, vacuum distillation removal solvent, petroleum ether elution, 75% ethyl alcohol are tied again after complete reaction
Crystalline substance crosses column purification, and 1- methyl-N- (2- oxo -2- (2- (2,3- dichlorophenyl amino shown in target compounds of formula (I -2) are made
Formoxyl) diazanyl) ethyl) -3- (trifluoromethyl) -1H- pyrazole-4-carboxamide, yield 64.4%, m.p.168-169 DEG C, formula
1- methyl-N- shown in (I -2) (2- oxo -2- (2- (2,3- dichlorophenyl carbamoyl) diazanyl) ethyl) -3- (fluoroform
Base) -1H- pyrazole-4-carboxamide structural formula is as follows：
1- methyl-N- (2- oxo -2- (2- (2,3- dichlorophenyl carbamoyl) diazanyl) ethyl) -3- (fluoroform
Base) -1H- pyrazole-4-carboxamide：1H NMR(500MHz,d-DMSO)δ:3.91 (d, J=5.5Hz, 2H, CH2),3.96(s,3H,
CH3), 7.31~7.34 (m, 2H, Ph), 8.01~8.06 (m, 1H, Ph), 8.38 (s, 1H, CH), 8.60 (t, J=5.5Hz,
1H,NH),8.89(s,1H,NH),9.26(s,1H,NH),10.02(s,1H,NH)；HRMS(ESI)m/z:Calculated,
453.0451,Found,453.0439[M+H]+.
Embodiment 3N- (2- (2- (the chloro- 2- fluorophenyl carbamyl of 4-) diazanyl) -2- oxoethyl) -1- methyl -3- (three
Methyl fluoride) -1H- pyrazole-4-carboxamide preparation
Phenyl isocyanate in 1 step of embodiment (3) is substituted for the chloro- 2- fluorophenylisocyanate of 4-, other operations
With embodiment 1, N- (2- (2- (the chloro- 2- fluorophenyl carbamyl of 4-) diazanyl) -2- oxoethyl) -1- methyl -3- (trifluoro is obtained
Methyl) -1H- pyrazole-4-carboxamide, yield 37.5%, m.p.201-202 DEG C, (2- (2- (the chloro- 2- fluorine of 4- of N- shown in formula (I -3)
Phenylcarbamoyl) diazanyl) -2- oxoethyl) -1- methyl -3- (trifluoromethyl) -1H- pyrazole-4-carboxamide structural formula is such as
Under：
N- (2- (2- (the chloro- 2- fluorophenyl carbamyl of 4-) diazanyl) -2- oxoethyl) -1- methyl -3- (trifluoromethyl) -
1H- pyrazole-4-carboxamide：1H NMR(500MHz,d-DMSO)δ:3.90 (d, J=5.5Hz, 2H, CH2),3.95(s,3H,
CH3), 7.22 (d, J=9.0Hz, 1H, Ph), 7.45~7.47 (m, 1H, Ph), 7.97 (s, 1H, Ph), 8.38 (s, 1H, CH),
8.44 (s, 1H, NH), 8.58 (t, J=6.0Hz, 1H, NH), 8.68 (s, 1H, NH), 9.98 (s, 1H, NH)；HRMS(ESI)m/
z:Calculated,437.0747,Found,437.0739[M+H]+.
Embodiment 4N- (2- (2- (4- (2- perfluoro propyl) phenylcarbamoyl) diazanyl) -2- oxoethyl) -1- methyl -
The preparation of 3- (trifluoromethyl) -1H- pyrazole-4-carboxamide
Phenyl isocyanate in 1 step of embodiment (3) is substituted for 4- (2- perfluoro propyl) phenyl isocyanate, other
Operation obtains N- (2- (2- (4- (2- perfluoro propyl) phenylcarbamoyl) diazanyl) -2- oxoethyl) -1- first with embodiment 1
Base -3- (trifluoromethyl) -1H- pyrazole-4-carboxamide, yield 50.9%, m.p.145-146 DEG C, N- (2- (2- shown in formula (I -4)
(4- (2- perfluoro propyl) phenylcarbamoyl) diazanyl) -2- oxoethyl) -1- methyl -3- (trifluoromethyl) -1H- pyrazoles -4-
Formamide structural formula is as follows：
N- (2- (2- (4- (2- perfluoro propyl) phenylcarbamoyl) diazanyl) -2- oxoethyl) -1- methyl -3- (trifluoro
Methyl) -1H- pyrazole-4-carboxamide：1H NMR(500MHz,d-DMSO)δ:3.90 (d, J=5.5Hz, 2H, CH2),3.96(s,
3H,CH3), 7.54 (d, J=8.5Hz, 2H, Ph), 7.76 (s, 2H, Ph), 8.39 (s, 1H, CH), 8.43 (s, 1H, NH), 8.69
(s,1H,NH),10.00(s,1H,NH)；HRMS(ESI)m/z:Calculated,553.1040,Found,553.1073[M+H
]+.
Embodiment 5N- (2- (2- (2- cyano-phenyl carbamyl) diazanyl) -2- oxoethyl) -1- methyl -3- (fluoroform
Base) -1H- pyrazole-4-carboxamide preparation
Phenyl isocyanate in 1 step of embodiment (3) is substituted for 2- cyano-phenyl isocyanates, other operations are the same as real
Example 1 is applied, N- (2- (2- (2- cyano-phenyl carbamyl) diazanyl) -2- oxoethyl) -1- methyl -3- (trifluoromethyl)-is obtained
1H- pyrazole-4-carboxamide, yield 63.4%, m.p.184-185 DEG C, (2- (2- (the 2- cyano-phenyl ammonia first of N- shown in formula (I -5)
Acyl group) diazanyl) -2- oxoethyl) -1- methyl -3- (trifluoromethyl) -1H- pyrazole-4-carboxamide structural formula is as follows：
N- (2- (2- (2- cyano-phenyl carbamyl) diazanyl) -2- oxoethyl) -1- methyl -3- (trifluoromethyl) -1H-
Pyrazole-4-carboxamide：1H NMR(500MHz,d-DMSO)δ:3.96 (d, J=7.5Hz, 5H, CH3+CH2), 7.07 (t, d, J=
8.0Hz, 1H, Ph), 7.14 (t, J=7.5Hz, 1H, Ph), 7.53 (t, J=8.0Hz, 1H, Ph), 7.83 (s, 1H, Ph), 8.07
(d, J=7.5Hz, 1H, NH), 8.39 (s, 1H, CH), 8.75 (s, 1H, NH), 10.61 (s, 1H, NH), 10.97 (s, 1H, NH)；
HRMS(ESI)m/z:Calculated,410.1183,Found,410.1182[M+H]+.
Embodiment 6N- (2- (2- (2- methyl -4- nitrophenylcarbamoyl) diazanyl) -2- oxoethyl) -1- methyl -3-
The preparation of (trifluoromethyl) -1H- pyrazole-4-carboxamide
Phenyl isocyanate in 1 step of embodiment (3) is substituted for 2- methyl -4- nitrophenyl isocyanate, other
Operation obtains N- (2- (2- (2- methyl -4- nitrophenylcarbamoyl) diazanyl) -2- oxoethyl) -1- first with embodiment 1
Base -3- (trifluoromethyl) -1H- pyrazole-4-carboxamide, yield 47.7%, m.p.212-213 DEG C.
N- (2- (2- (2- methyl -4- nitrophenylcarbamoyl) diazanyl) -2- oxoethyl) -1- methyl -3- (fluoroform
Base) -1H- pyrazole-4-carboxamide：1H NMR(500MHz,d-DMSO)δ:2.34(s,3H,CH3), 3.91 (d, J=6.0Hz, 2H,
CH2),3.96(s,3H,CH3), 8.05~8.08 (m, 1H, Ph), 8.11 (d, J=2.5Hz, 1H, Ph), 8.16-8.19 (m, 1H,
), Ph 8.31 (t, J=9.0Hz, 1H, NH), 8.38 (s, 1H, CH), 8.61 (s, 1H, NH), 8.84 (s, 1H, NH), 10.07 (s,
1H,NH)；HRMS(ESI)m/z:Calculated,444.1238,Found,444.1252[M+H]+.
The test of 7 activity of weeding of embodiment
Subjects：The seed of romaine lettuce (Lettuce), bent grass (Agrostis).
Test process：Seed treatment：Before bioassay, seed uses the Chlorox solution of 5-10% to carry out 10
The surface sterilizing of minute then carries out cleaning down with the deionized water of Millipore system, then in gnotobasis apoplexy
It is dry.Sample treatment：All samples use acetone as solvent, and configuration concentration is the solution of 1mM, place stand-by.
Bioassay：All bioassay are divided into duplicate measurement, thin in sterile 24 hole of apyrogeneity polystyrene
It is carried out in born of the same parents' culture plate (CoStar 3524, Corning Incorporated).By a filter paper disk (Whatman Grade
It 1,1.5cm) is placed in each hole ready for use.There are 200 μ L water in all control wells, contains 180 μ L in control+solvent hole
Water and 20 μ L solvents, and have 180 μ L water and the suitably diluted sample of 20 μ L in all sample wells.Before sample is added,
It first will be in 180 μ L water inlet holes.All plates are both placed in sterile environment, and reduce the machine of pollution as far as possible
Meeting.5 seeds are put into all Kong Zhongjun, are sealed with lid.Plate is placed in the incubator of CU-36L5, temperature is 26 DEG C,
Intensity of illumination is 120.1umol s-1m-2Under conditions of be incubated for, plate is at least incubated for 7 days, relatively subjective rows of plants is obtained
Name.Ranking is divided into 5 grades：0-5.Grade be 0 expression do not have apparent inhibiting effect (sample well plant with compare+it is molten
Plant is identical in agent hole), class 5 is expressed as completely inhibiting, i.e., seed all in hole absolutely not germinates.
Activity of weeding test result is as shown in table 1.
The activity of weeding of each compound under 1 1mm of table
It is obtained from table 1, preferable inhibition, especially chemical combination is shown to romaine lettuce under compound 1mm of the present invention
Object (6)；Preferable inhibition is all shown to romaine lettuce, bent grass.
Claims (3)
1. a kind of amides compound containing pyrazole ring is preparing the application in herbicide, it is characterised in that its structural formula such as formula
（Ⅰ）It is shown：
（Ⅰ）
Formula（Ⅰ）In：R is phenyl or substituted-phenyl, and the substituent group of the substituted-phenyl is halogen, 2- perfluoro propyl, cyano, first
Base, nitro.
2. a kind of application of amides compound containing pyrazole ring in the herbicide of preparation prevention and treatment romaine lettuce and bent grass, feature
It is its structural formula such as formula（Ⅰ）It is shown：
（Ⅰ）
Formula（Ⅰ）In：R is phenyl or substituted-phenyl, and the substituent group of the substituted-phenyl is halogen, 2- perfluoro propyl, cyano, first
Base, nitro.
3. application according to claim 1 or 2, it is characterised in that formula（Ⅰ）Middle R is one of following：Phenyl, 2,3- dichloro-benzenes
Base, the chloro- 2- fluorophenyl of 4-, 4-（2- perfluoro propyl）Phenyl, 2- cyano-phenyl, 2- methyl -4- nitrobenzophenone.
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| CN113563329A (en) * | 2021-04-16 | 2021-10-29 | 上海搜果科技有限公司 | Novel pyridopyrimidinedione compound and preparation method and application thereof |
| CN114181150A (en) * | 2021-12-09 | 2022-03-15 | 沈阳万菱生物技术有限公司 | Pyrazole amide derivative, preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113563329A (en) * | 2021-04-16 | 2021-10-29 | 上海搜果科技有限公司 | Novel pyridopyrimidinedione compound and preparation method and application thereof |
| CN114181150A (en) * | 2021-12-09 | 2022-03-15 | 沈阳万菱生物技术有限公司 | Pyrazole amide derivative, preparation method and application thereof |
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