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CN103524418A - 3-methyl pyrazol compounds - Google Patents

3-methyl pyrazol compounds Download PDF

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Publication number
CN103524418A
CN103524418A CN201310527240.2A CN201310527240A CN103524418A CN 103524418 A CN103524418 A CN 103524418A CN 201310527240 A CN201310527240 A CN 201310527240A CN 103524418 A CN103524418 A CN 103524418A
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compound
preparation
methylpyrazole
rxh
pathogenic bacteria
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CN103524418B (en
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孙家隆
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Qingdao Agricultural University
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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
    • 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
    • C07D417/12—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)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention provides 3-methyl pyrazol compounds. According to the general formula of the 3-methyl pyrazol compounds, X is NH or O or S, and an R group is selected from a phenyl derivative or a naphthyl derivative or a heterocyclic radical derivative. The structure of the compounds and the control efficiency of the compounds on agricultural diseases are disclosed, and meanwhile the application of the compounds as sterilizing agents is disclosed.

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 take its sterilant application that is activeconstituents.
Background technology
Pyrazole compound has high biological activity, more and more noticeable as the application of agricultural chemicals aspect.For example, the pyrrole metsulfovax of the systemic fungicide furametpyr of SUMITOMO CHEMICAL company exploitation, the exploitation of Mitsui chemical company is all good 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 suc as formula shown in I:
Figure BSA0000096941630000011
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
Figure BSA0000096941630000021
The preparation method that a further object of the present invention is to provide described compound is as follows:
Reaction equation:
Figure BSA0000096941630000022
Comprise the following steps: in room temperature, the inert solvent solution of the chloro-4-pyrazol formyl chloride of 1,3-dimethyl-5-is added dropwise to RXH and K 2cO 3inert solvent solution in, after dropwising, rise at 20～50 ℃ of temperature and react, after completion of the reaction suction filtration, remove reaction solvent, after recrystallization purifying, obtain described compound.
Concrete, described RXH is selected from any one corresponding with compound number in table 2.
The required RXH of table 2 preparation 3-methylpyrazole compound of the present invention
Figure BSA0000096941630000023
Concrete, while 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, described 1, the chloro-4-pyrazol formyl chloride of 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, part of compounds has the activity that suppresses pathogenic bacteria growth, and can obtain good effect.
It is one of key character of the present invention that 3-methylpyrazole compound provided by the invention is used 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 relatively environmental protection while producing as bactericide agricultural chemicals.
Embodiment
The present invention is by preparation and the biological activity of specific preparation and biological activity determination embodiment specific description 3-methylpyrazole provided by the present invention compound, and described embodiment is unrestricted the present invention for specific description the present invention only.
The experimental technique using in following embodiment if no special instructions, is ordinary method.
In following embodiment, material used, reagent etc., if no special instructions, all can obtain from commercial channels.
The preparation of embodiment 1 compound T110906
In being equipped with the there-necked flask of 100 milliliters of thermometer, agitator and condenser, add 5 mmole anhydrous K 2cO 3powder, 5 mmoles 2,6-xylidine, 35 milliliters of chloroforms, the lower chloro-4-pyrazol formyl chloride of 5 mmole 1-methyl-3-trifluoromethyl-5-that slowly drips of low temperature (0 ± 5 ℃) is dissolved in the solution that 25 milliliters of chloroforms are made into, dropwise, slowly be warming up to room temperature (20 ± 5 ℃), and in stirring at room reaction 6 hours.Filtration under diminished pressure reaction mixture, by gained filtrate decompression precipitation, make compound T110906 crude product, use ethanol-sherwood oil (volume ratio 3:1) to compound T110906 crude product recrystallization, make needle-like white crystal compound T110906 sterling, yield 94%.
The preparation of other 29 kinds of compounds in embodiment 2～30 tables 1
Concrete operations are as table 3.
Table 3 embodiment 2～24 concrete operations
Figure BSA0000096941630000041
Figure BSA0000096941630000051
The physical and chemical parameter of the prepared compound of embodiment 31 embodiment 1-30 is measured and Identification of chemical structure
The fusing point of the prepared compound of mensuration embodiment 1-30, 1h-NMR and IR, its chemical structural formula and physical and chemical parameter in Table 4, table 5 and table 6.
3-methylpyrazole compound physical chemical property and yield that table 4 embodiment 1-30 is prepared
Figure BSA0000096941630000061
Figure BSA0000096941630000071
Figure BSA0000096941630000081
The 3-methylpyrazole compound proton nmr spectra data that table 5 embodiment 1-30 is prepared
Figure BSA0000096941630000082
Figure BSA0000096941630000091
The 3-methylpyrazole compound ir data that table 6 embodiment 1-30 is prepared
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 that embodiment 1-30 is prepared 1h-NMR shows with number and its structure of the corresponding chemical shift of its structure, H identical, and corresponding skeleton absorption peak appears in IR.
The Antibacterial Activity of the prepared 3-methylpyrazole compound of embodiment 32 embodiment 1-30 to 7 kinds of common representative disease cause of diseases
(1) PDA substratum preparation: 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, standby.
(2) cultivation of pathogenic fungi: with a small amount of pathogenic bacteria mycelia of inoculating needle picking, on PDA substratum, be placed in 25 ℃ of constant incubators and cultivate 2-4 days, stand-by after mycelia grows.
(3) measuring method: adopt mycelial growth rate method (size of colony diameter in certain hour) to measure the bacteriostatic activity of compound.In centrifuge tube, accurately take 5mg for examination target compound, first by proper amount of acetone, dissolve, then add the aqueous solution that contains 1% polysorbas20 emulsifying agent of calculated amount, be diluted to the liquid of 1000mg/L.Get 1mL liquid and add in 9mL substratum and shake up, be mixed with the pastille substratum of 100mg/L, evenly pour culture dish into.Do not add and do blank containing the acetone that tries target compound altogether, contains same amount and the culture dish of polysorbas20 emulsifying agent substratum simultaneously.At well-grown, pollution-free with the punch tool (diameter 4mm) of sterilizing, the even colony edge of growing way is beaten and is got bacterium cake, under aseptic condition, access pastille substratum center (a bacterium cake of each culture dish inoculation), cover ware lid, ware covers down, and every processing repeats 3 times.Substratum is placed in to 25 ℃ of constant incubators and cultivates, after colony diameter expands to 4-5cm in contrast culture ware, by right-angled intersection method, measure and respectively process bacterium cake expansion diameter, average, relatively calculate relative bacteriostasis rate with blank.
(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 the fungistatic effect of the prepared 3-methylpyrazole compound of embodiment 1-30 to seven kinds of common representative disease cause of diseases, measurement result is (in table, data be the inhibition percentage that each compound is grown to pathogenic bacteria when 100mg/L) in Table 7.
Wherein, establish Azoxystrobin for contrast agricultural chemicals.
The 3-methylpyrazole compound fungicidal activity that table 7 embodiment 1-30 is prepared
Figure BSA0000096941630000111
Figure BSA0000096941630000121
From table 7, data are found out, the prepared compound of embodiment 1-30 is under 100mg/L concentration, selected seven kinds of pathogenic bacteria great majority are had to bacteriostatic activity in various degree, wherein T110915 to the bacteriostasis rate of tomato early blight bacterium reach respectively 93.95%, T111015 to the bacteriostasis rate of Pear black spot bacterium reach 100.00%, T111020 to the bacteriostasis rate of withered germ of water-melon reach 100.00%, T120603 and T120604 reach respectively 89.66% and 100.00% to Valsa mali bacteriostasis rate, bacteriostasis rate is higher than contrast agricultural chemicals Azoxystrobin.

Claims (10)

1. one group of 3-methylpyrazole compound, structural formula is suc as formula shown in I:
Figure FSA0000096941620000011
Wherein, X is NH, O or S, and R group is selected from phenyl derivatives, naphthyl derivatives or heterocyclic radical derivative.
2. 3-methylpyrazole compound according to claim 1, is characterized in that: have formula I structure, wherein said compound is selected from any one in following table.
Figure FSA0000096941620000012
Figure FSA0000096941620000021
。
3. the preparation method of compound described in claim 1 or 2, comprises the following steps: in room temperature, the inert solvent of the chloro-4-pyrazol formyl chloride of 1,3-dimethyl-5-(acetonitrile or chloroform or toluene) solution is added dropwise to RXH and K 2cO 3inert solvent (acetonitrile or chloroform or toluene) solution in, after dropwising, rise at 20～50 ℃ of temperature and react, after completion of the reaction suction filtration, remove reaction solvent, after recrystallization purifying, obtain described compound.
4. preparation method according to claim 3, is characterized in that: described RXH is selected from any one in following table.
Figure FSA0000096941620000022
。
5. according to the preparation method described in claim 3 or 4, it is characterized in that: while preparing compound T111021, T111022 in claim 2, 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 claim 2 during other compounds, described 1, the chloro-4-pyrazol formyl chloride of 3-dimethyl-5-, RXH and K 2cO 3molar mass than for 1:1:1.
6. the application of the 3-methylpyrazole compound described in claim 1 or 2 in control farm crop agricultural disease.
7. the 3-methylpyrazole compound described in claim 1 or 2 is suppressing pathogenic bacteria growth or is killing the application in pathogenic bacteria.
8. the 3-methylpyrazole compound described in claim 1 or 2 suppresses pathogenic bacteria growth or kills the application in pathogenic bacteria medicine in preparation.
9. an agricultural composition, acceptable carrier and/or vehicle in the compound in its claim that comprises 0.1～99.9 % by weight 1 and claim 2 described in any one and Pesticide Science.
10. the purposes of agricultural composition according to claim 9, is characterized in that: as the application in disinfectant use in agriculture.
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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
CN108069905A (en) * 2016-11-09 2018-05-25 沈阳中化农药化工研发有限公司 A kind of pyrazol acid amide compounds and its application
CN112939942A (en) * 2020-12-24 2021-06-11 聊城大学 Heterocyclic ester compound containing quinoline structure and preparation method and application thereof

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Cited By (5)

* Cited by examiner, † Cited by third party
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CN108069905A (en) * 2016-11-09 2018-05-25 沈阳中化农药化工研发有限公司 A kind of pyrazol acid amide compounds and its application
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CN112939942A (en) * 2020-12-24 2021-06-11 聊城大学 Heterocyclic ester compound containing quinoline structure and preparation method and application thereof
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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