CN103524418B - One group of 3-methylpyrazole compound - Google Patents

One group of 3-methylpyrazole compound Download PDF

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CN103524418B
CN103524418B CN201310527240.2A CN201310527240A CN103524418B CN 103524418 B CN103524418 B CN 103524418B CN 201310527240 A CN201310527240 A CN 201310527240A CN 103524418 B CN103524418 B CN 103524418B
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compound
disease
methylpyrazole
rxh
preparation
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CN103524418A (en
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孙家隆
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Qingdao Agricultural University
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    • 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
    • C07D231/16—Halogen atoms or nitro radicals
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention provides one group of 3-methylpyrazole compound, this compound formula is

Description

One group of 3-methylpyrazole compound
Technical field
The invention belongs to pesticide field, technical scheme relates to one group of 3-methylpyrazole compound and preparation method thereof and applies with its sterilant being activeconstituents.
Background technology
Pyrazole compound has high biological activity, and the application as agricultural chemicals aspect is more and more noticeable.Such as, the systemic fungicide furametpyr of SUMITOMO CHEMICAL company exploitation, the pyrrole metsulfovax of Mitsui chemical company exploitation are all excellent disinfectant use in agriculture.We conduct in-depth research analysis to pyrazole compound structure, according to row's principles such as bioelectricity, with 1, the chloro-4-pyrazol formyl chloride of 3-dimethyl-5-is parent, react from different nucleophilic reagents respectively, synthesized serial 3-methylpyrazole compound, biological activity test result shows, prepared compound has good sterilization, bacteriostatic action.
Summary of the invention
The object of this invention is to provide one group of 3-methylpyrazole compound, structural formula is such as formula shown in I:
Wherein, X is NH, O or S, and R group is selected from phenyl derivatives, naphthyl derivatives or heterocyclic radical derivative.
Concrete, compound shown in formula I is any one in table 1.
Table 1 3-methylpyrazole provided by the invention compound
The preparation method that another object of the present invention is to provide described compound is as follows:
Reaction equation:
Comprise the following steps: in room temperature, the inert solvent solution of chloro-for 1,3-dimethyl-5-4-pyrazol formyl chloride is added dropwise to RXH and K 2cO 3inert solvent solution in, after dropwising, react under rising to 20 ~ 50 DEG C of temperature, after completion of the reaction suction filtration, remove reaction solvent, after recrystallization purifying, namely obtain described compound.
Concrete, described RXH is selected from any one corresponding with compound number in table 2.
RXH needed for 3-methylpyrazole compound of the present invention prepared by table 2
Concrete, when preparing compound T111021, T111022, T120604 and T120605, RXH is respectively 2-sulfurous base imidazolidine, N-nitro imido imidazolyl alkane, 2-sulfydryl-5-amino 3,4-thiadiazoles and 2,5-diamino 3,4-thiadiazoles, and the chloro-4-pyrazol formyl chloride of 1,3-dimethyl-5-, RXH and K 2cO 3molar mass than for 2:1:2; In preparation table 1 during other compounds, the chloro-4-pyrazol formyl chloride of described 1,3-dimethyl-5-, RXH and K 2cO 3molar mass than for 1:1:1.
Concrete, described inert solvent is acetonitrile, chloroform or toluene.
It is disinfectant use in agriculture application that another object of the present invention is to provide described 3-methylpyrazole compound.
The invention has the beneficial effects as follows: 3-methylpyrazole compound of the present invention can be used for preventing and treating agricultural disease, and part of compounds has the activity suppressing growth of pathogenic bacteria, and can obtain good effect.
3-methylpyrazole compound provided by the invention is one of key character of the present invention for preventing and treating agricultural disease.
" three wastes " that produce in new compound preparation process of the present invention are less, are easy to process, compare environmental protection when producing as bactericide agricultural chemicals.
Embodiment
The present invention is by the preparation of specific preparation and biological activity determination embodiment specific description 3-methylpyrazole provided by the present invention compound and biological activity, and described embodiment is unrestricted the present invention for specific description the present invention only.
The experimental technique used in following embodiment if no special instructions, is ordinary method.
Material used in following embodiment, reagent etc., if no special instructions, all can obtain from commercial channels.
The preparation of embodiment 1 compound T110906
5 mmole anhydrous K are added in the there-necked flask of 100 milliliters being equipped with thermometer, agitator and condenser 2cO 3powder, 5 mmoles 2,6-xylidine, 35 milliliters of chloroforms, under low temperature (0 ± 5 DEG C), the chloro-4-pyrazol formyl chloride of slow dropping 5 mmole 1-methyl-3-trifluoromethyl-5-is dissolved in the solution that 25 milliliters of chloroforms are made into, dropwise, slowly be warming up to room temperature (20 ± 5 DEG C), and react 6 hours in stirring at room temperature.Filtration under diminished pressure reaction mixture, by gained filtrate decompression precipitation, obtained compound T110906 crude product, with ethanol-sherwood oil (volume ratio 3:1) to compound T110906 crude product recrystallization, obtained needle-like white crystals compound T110906 sterling, yield 94%.
The preparation of other 29 kinds of compounds in embodiment 2 ~ 30 table 1
Concrete operations are as table 3.
Table 3 embodiment 2 ~ 24 concrete operations
The physical and chemical parameter of compound prepared by embodiment 31 embodiment 1-30 measures and Identification of chemical structure
Measure the fusing point of compound prepared by embodiment 1-30, 1h-NMR and IR, its chemical structural formula and physical and chemical parameter are in table 4, table 5 and table 6.
3-methylpyrazole compound physical chemical property prepared by table 4 embodiment 1-30 and yield
3-methylpyrazole compound hydrogen nuclear magnetic resonance modal data prepared by table 5 embodiment 1-30
3-methylpyrazole compound ir data prepared by table 6 embodiment 1-30
Numbering Infrared spectra (charateristic avsorption band) data (IR)/cm -1
T110906 3224，3033，2921，1635，1540，1515，1457，1373，1304
T110907 3253，2037，2934，1635，1532，1399，1376，1270
T110908 3406，3257，3095，2929，1673，1652，1586，1544，1441，1377，1308
T110911 3274，3170，3100，2925，1947，1648，1582，1572，1474，1403，1373
T110913 3440，3178，2983，1677，1573，1532，1432，1374
T110915 3390，3282，2988，2925，2855，1764，1652，1586，1499，1436，1378
T110916 3361，3095，2988，2934，1685，1602，1544，1494，1378，1374
T110917 3378，3012，2922，1926，1768，1661，1542，1408，1369
T110918 3153，3050，2929，1677，1598，1548，1528，1445，1370，1378
T110919 3120，3046，2983，2925，1660，1519，1416，1362，1370
T110920 3323，3098，2987，1668，1518，1416，1376
T110921 3502，3211，3021，2704，1627，1515，1378
T110922 3344，3017，2942,2884,2187，1681，1573，1465，1370
T110923 3382，2975，2921，1698，1673，1602，1544，1515，1490，1436，1370
T111013 3236，3166,3062,2909，1685，1598，1553，1519，1482，1432，1376
T111014 3153，2979,2943，2908,2839，1673，1530，1441，1373
T111015 3315，3129,2992，1664，1503，1403，1374
T111016 3382，2958,2921，1673，1577，1511，1378，1374
T111019 3070，2963，2871，2842，1652，1598，1507，1461，1366
T111020 2992，2929，1685，1664，1519，1474，1378，1366
T111021 3432，2942，1706，1664，1582，1515，1461，1395
T111022 3423，2938，1685，1664，1582，1515，1461，1395
T111023 3427，3270,3054,2954，1727，1615，1569，1478，1387
T111024 3427，3270,3054,2954，1727，1615，1596，1478，1387
T120601 3448，3236,3141，2934,2793，1677，1573，1523，1436，1366
T120602 3402，2975，2929,2788，1660，1569，1424,1371
T120603 3423，3108,2988,2954，1652，1573，1436，1333
T120604 3377，3116，2954，1644，1511，1441，1304
T120605 3440，2996,2954，1648，1573，1519，1445
T130422 3440，2067，1640，1573，1523，1432，1304，1266
From table 5 and table 6, the 3-trifluoromethyl pyrazol compound prepared by embodiment 1-30 1number and its structure of the H-NMR display chemical shift corresponding to its structure, H are identical, and corresponding skeleton absorption peak appears in IR.
3-methylpyrazole compound prepared by embodiment 32 embodiment 1-30 is to the Antibacterial Activity of 7 kinds of common representative disease cause of diseases
(1) PDA medium preparing: by the stripping and slicing of 200g peeling potatoes, add 1000mL distilled water, boil 10-20min.By filtered through gauze, add distilled water to 1000mL.Add 20g glucose and 17g agar, heating and melting, packing, high pressure steam sterilization 2h, for subsequent use.
(2) cultivation of pathogenic fungi: with a small amount of pathogenic bacteria mycelia of inoculating needle picking on PDA substratum, be placed in 25 DEG C of constant incubators and cultivate 2-4 days, stand-by after mycelia grows.
(3) measuring method: adopt the mycelial growth rate method size of colony diameter (in the certain hour) to measure the bacteriostatic activity of compound.In centrifuge tube, accurately take 5mg for examination target compound, first dissolve by proper amount of acetone, then add the aqueous solution containing 1% polysorbas20 emulsifying agent of calculated amount, be diluted to the liquid of 1000mg/L.Get 1mL liquid to add in 9mL substratum and shake up, be mixed with the pastille substratum of 100mg/L, evenly pour culture dish into.Add simultaneously and do not do blank containing the culture dish trying target compound, acetone containing identical amount and polysorbas20 emulsifying agent substratum altogether.With the punch tool (diameter 4mm) of sterilizing at well-grown, pollution-free, the even colony edge of growing way is beaten and is got bacterium cake, aseptically access pastille substratum center (a bacterium cake inoculated by each culture dish), cover ware lid, ware lid, often processes repetition 3 times down.Substratum is placed in 25 DEG C of constant incubators to cultivate, after colony diameter in contrast culture dish expands to 4-5cm, measures each process bacterium cake expansion diameter by right-angled intersection method, average, compare with blank and calculate relative bacteriostasis rate.
(4) calculating of bacteriostasis rate:
Bacterium colony increases diameter (mm)=bacterium colony and measures diameter (mm)-bacterium cake diameter (mm)
Relative inhibition (%)=[contrast bacterium colony increases bacterium colony on diameter (mm)-pastille substratum and increases diameter (mm)]/contrast bacterium colony increases diameter (mm) × 100
According to the method described above, measure 3-methylpyrazole compound prepared by embodiment 1-30 to the fungistatic effect of seven kinds of common representative disease cause of diseases, measurement result is in table 7 (inhibition percentage that in table, data are each compound when 100mg/L to growth of pathogenic bacteria).
Wherein, if Azoxystrobin is contrast agricultural chemicals.
3-methylpyrazole compound fungicidal activity prepared by table 7 embodiment 1-30
From table 7, data are found out, compound prepared by embodiment 1-30 is under 100mg/L concentration, to the most of bacteriostatic activity had in various degree of selected seven kinds of pathogenic bacterias, wherein T110915 reaches 93.95% respectively to the bacteriostasis rate of tomato early blight bacterium, the bacteriostasis rate of T111015 to Pear black spot bacterium reaches 100.00%, the bacteriostasis rate of T111020 to withered germ of water-melon reaches 100.00%, T120603 and T120604 reaches 89.66% and 100.00% respectively to Valsa mali bacteriostasis rate, and bacteriostasis rate is higher than contrast agricultural chemicals Azoxystrobin.

Claims (6)

1. one group of 3-methylpyrazole compound, described compound and structural formula thereof be selected from following table any one:
2. the preparation method of compound described in claim 1: be added dropwise to RXH and K by the acetonitrile of chloro-for 1,3-dimethyl-5-4-pyrazol formyl chloride or chloroform or toluene solution in room temperature 2cO 3acetonitrile or chloroform or toluene solution in, after dropwising, react under rising to 20 ~ 50 DEG C of temperature, after completion of the reaction suction filtration, remove reaction solvent, after recrystallization purifying, namely obtain described compound, described RXH be selected from following table any one:
3. preparation method according to claim 2, it is characterized in that: in preparation claim 1 when compound T111021, T111022, T120604 and T120605, RXH is respectively 2-sulfurous base imidazolidine, N-nitro imido imidazolyl alkane, 2-sulfydryl-5-amino 3,4-thiadiazoles and 2,5-diamino 3,4-thiadiazoles, and the chloro-4-pyrazol formyl chloride of 1,3-dimethyl-5-, RXH and K 2cO 3mole ratio be 2: 1: 2, preparation claim 1 in other compound time, the chloro-4-pyrazol formyl chloride of 1,3-dimethyl-5-, RXH and K 2cO 3mole ratio be 1: 1: 1.
4. the application of 3-methylpyrazole compound according to claim 1 in control farm crop agricultural disease.
5. 3-methylpyrazole compound according to claim 1 is in the application suppressing growth of pathogenic bacteria or kill in pathogenic bacteria, and the microbial disease of wherein said cause of disease does not comprise the disease of human body or animal body.
6. 3-methylpyrazole compound according to claim 1 is preparing the application suppressing growth of pathogenic bacteria or kill in pathogenic bacteria medicine, and the microbial disease of wherein said cause of disease does not comprise the disease of human body or animal body.
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CN108069905B (en) * 2016-11-09 2020-08-04 沈阳中化农药化工研发有限公司 Pyrazole amide compound and application thereof
CN107141283A (en) * 2017-07-04 2017-09-08 安徽农业大学 The preparation of the pyrazoles ester derivative of one class ring skeleton containing triazole and its it is used as the application of bactericide
CN112939942B (en) * 2020-12-24 2023-11-07 聊城大学 Heterocyclic ester compound containing quinoline structure, and preparation method and application thereof

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