CN103554026A - 3-trifluoromethyl-4-formyl pyrazole compounds - Google Patents
3-trifluoromethyl-4-formyl pyrazole compounds Download PDFInfo
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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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—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
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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
- A01N43/72—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
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- 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
- C07D417/12—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
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract
The invention provides a group of 3-trifluoromethyl-4-formyl pyrazole compounds. The compounds have a general formula shown in the specification, wherein X is NH, O or S; and the R group is selected from phenyl derivatives, naphthyl derivatives or heterocyclic radical derivatives. The invention also discloses structures of the compounds and effects og preventing and treating agricultural diseases, as well as application of the compounds serving as bactericides.
Description
Technical field
The invention belongs to pesticide field, technical scheme relates to one group of 3-trifluoromethyl-4-formyl pyrazole compound, is specifically related to one group of 3-trifluoromethyl-4-formyl pyrazole derivatives and preparation method thereof and take its sterilant application that is activeconstituents.
Background technology
Pyrazole compound has high biological activity, and this compounds is as the application of agricultural chemicals, more and more noticeable.For example, the fenpyroximate that Mitsubishi changes into Co., Ltd. exploitation tebufenpyrad, Nihon Nihyaku Co., Ltd's exploitation is all that the systemic fungicide furametpyr of the quick miticide ，Er SUMITOMO CHEMICAL company exploitation of high-efficiency broad spectrum, the pyrrole metsulfovax of Mitsui chemical company exploitation are used as good disinfectant use in agriculture.We conduct in-depth research analysis to pyrazole compound structure, according to row's principles such as bioelectricity, trifluoromethyl is introduced to pyrazole ring, 1-methyl-3-trifluoromethyl-4-pyrazol formyl chloride of take is parent, react from different nucleophilic reagents respectively, synthesize serial 3-trifluoromethyl-4-formyl pyrazole compound, and measured its fungicidal activity.
Summary of the invention
The object of this invention is to provide one group of 3-trifluoromethyl-4-formyl pyrazole compound, structural formula is suc 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-trifluoromethyl-4-provided by the invention formyl pyrazole compound
A further object of the present invention is to provide the preparation method of described compound, as follows:
Reaction equation:
Comprise the following steps: under low temperature (0 ± 5 ℃), the inert solvent solution of 1-methyl-3-trifluoromethyl-4-pyrazol formyl chloride is added dropwise to RXH and K
2cO
3inert solvent solution in, after dropwising, rise to room temperature (25 ± 5 ℃) reaction, 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 of table 2.
The required RXH of table 2 preparation 3-trifluoromethyl-4-formyl pyrazole compound of the present invention
Concrete, described 1-methyl-3-trifluoromethyl-4-pyrazol formyl chloride, 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-trifluoromethyl-4-formyl pyrazole compound.
The invention has the beneficial effects as follows: 3-trifluoromethyl-4-formyl pyrazole 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-trifluoromethyl-4-formyl pyrazole 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-trifluoromethyl-4-formyl pyrazole 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 Q 120209
In being housed, the there-necked flask of 100 milliliters of thermometer and agitator adds 0.01 mole of anhydrous K
2cO
3powder, 0.01 mole of 3-monomethylaniline, 30 milliliters of acetonitriles, 0.01 mole of 1-methyl-3-trifluoromethyl-4-pyrazol formyl chloride of the lower slowly dropping of room temperature (25 ± 5 ℃) is dissolved in the solution that 20 milliliters of acetonitriles are made into, dropwise, in room temperature, continue stirring reaction 10 hours.Filtration under diminished pressure reaction mixture, by gained filtrate decompression precipitation, makes compound Q 120209 crude products, with ethanol-toluene (volume ratio 1:1), to compound Q 120209 crude product recrystallizations, makes white plates crystalline compounds Q120209, yield 64.2%.
The preparation of other 17 kinds of compounds in embodiment 2～18 tables 1
Concrete operations are as table 3.
Table 3 embodiment 2～18 concrete operations
The physical and chemical parameter of the prepared compound of embodiment 19 embodiment 1-18 is measured and Identification of chemical structure
The fusing point of the prepared compound of mensuration embodiment 1-18,
1h-NMR and IR, its chemical structural formula and physical and chemical parameter in Table 4, table 5 and table 6.
3-trifluoromethyl-4-formyl pyrazole compound physicochemical property and yield that table 4 embodiment 1-18 is prepared
3-trifluoromethyl-4-formyl pyrazole compound that table 5 embodiment 1-18 is prepared
1h-NMR data
3-trifluoromethyl-4 formyl pyrazole compound the ir data that table 6 embodiment 1-18 is prepared
| Numbering | Infrared spectra (charateristic avsorption band) data (IR)/cm -1 |
| Q120209 | IR(KBr)v：3489，3411，3174，1652，1611，1557，1486，1324，1217，1138 |
| Q120210 | IR(KBr)v：3224，1644，1557，1482，1395，1308，1270，1179 |
| Q120510 | IR(KBr)v：3299，3162，3100，1669，1582，1523，1494，1461，1387，1304 |
| Q120305 | IR(KBr)v：3485，3382，3278，1656，1598，1494，1329，1250，1175，1146 |
| Q120825 | IR(KBr)v：3245，1652，1565，1507，1441，1316，1217，1183 |
| Q120915 | IR(KBr)v：3506，3120，3058，1656，1590，1540，1474，1416，1321，1146 |
| Q120627 | IR(KBr)v：3290，3195，3133，1656，1606，1548，1519，1407，1324，1175 |
| Q120827 | IR(KBr)v：3494，3373，3261，1664，1602，1561，1329，1300，1188 |
| Q130304 | IR(KBr)v：2963，1652，1565，1432，1337，1175，1134，1059，839，777，711 |
| Q130305 | IR(KBr)v：3241，1652，1557，1519，1432，1329，1300，1208，1146，1051，827，752 |
| Q130306 | IR(KBr)v：3290，1660，1561，1523，1436，1300，1134，1059，856，823，711，648 |
| Q130307 | IR(KBr)v：2958，1785，1640，1565，1424，1333，1291，1146，1047，847，781，706 |
| Q130310 | IR(KBr)v：3456，3054，2963，1694，1627，1557，1424，1341，1308，1171，1129 |
| Q130311 | IR(KBr)v：3456，3070，2963，1694，1627，1557，1424，1341，1308，1183，885，711 |
| Q130314 | IR(KBr)v：3452，1677，1627，1557，1420，1275，1138，1088，1017，868，764 |
| Q130317 | IR(KBr)v：3452，1635，1561，1438，1338，1134，872，781，732，623 |
| Q130319 | IR(KBr)v：3170，3116，3054，1689，1557，1436，1316，1175，1134，1059，1005，872 |
| Q130320 | IR(KBr)v：1627，1553，1436，1329，1142，839，781，711，619，516 |
From table 5 and table 6,3-trifluoromethyl-4-formyl pyrazole compound that embodiment 1-18 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-trifluoromethyl-4-formyl pyrazole compound of embodiment 20 embodiment 1-18 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-trifluoromethyl-4-formyl pyrazole compound of embodiment 1-18 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, Azoxystrobin is contrast agricultural chemicals.
3-trifluoromethyl-4-formyl pyrazole compound fungicidal activity that table 7 embodiment 1-18 is prepared
From table 7, data are found out, the prepared compound of embodiment 1-18 is under 100mg/L concentration, selected seven kinds of pathogenic bacteria great majority are had to bacteriostatic activity in various degree, wherein the bacteriostasis rate of Q120627 Pear black spot bacterium reach respectively 100.00%, Q130307 to the bacteriostasis rate of Valsa mali reach 91.70%, Q130314 reaches 94.70% to the bacteriostasis rate of tomato early blight bacterium, bacteriostasis rate higher than or close to contrast agricultural chemicals Azoxystrobin.
Claims (10)
1. one group of 3-trifluoromethyl-4-formyl pyrazole compound, structural formula is suc 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.
2. 3-trifluoromethyl-4-formyl pyrazole compound according to claim 1, is characterized in that: have formula I structure, wherein said compound is selected from any one in following table.
3. the preparation method of compound described in claim 1 or 2, comprises the following steps: under low temperature (0 ± 5 ℃), inert solvent (acetonitrile or chloroform or the toluene) solution of 1-methyl-3-trifluoromethyl-4-pyrazol formyl chloride is added dropwise to RXH and K
2cO
3inert solvent (acetonitrile or chloroform or toluene) solution in, after dropwising, rise to room temperature (25 ± 5 ℃) reaction, 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 corresponding with compound number in following table.
5. according to the preparation method described in claim 3 or 4, it is characterized in that: described 1-methyl-3-trifluoromethyl-4-pyrazol formyl chloride, RXH and K
2cO
3molar mass than for 1:1:1.
6. the application of the trifluoromethyl-4-of the 3-described in claim 1 or 2 formyl pyrazole compound in control farm crop agricultural disease.
7. trifluoromethyl-the 4-of the 3-described in claim 1 or 2 formyl pyrazole compound is suppressing pathogenic bacteria growth or is killing the application in pathogenic bacteria.
8. trifluoromethyl-the 4-of the 3-described in claim 1 or 2 formyl pyrazole compound 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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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632044A (en) * | 2016-12-30 | 2017-05-10 | 浙江工业大学 | Amide compound containing methylpyrazole and preparation method the application thereof |
| CN107935929A (en) * | 2017-12-01 | 2018-04-20 | 浙江工业大学 | 3 trifluoromethyl 1H pyrazoles of a kind of 1 methyl, 4 amide derivatives and preparation method and application |
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| CN1646494A (en) * | 2002-02-19 | 2005-07-27 | 拜尔农作物科学股份公司 | Disubstituted pyrazolyl carboxanilides |
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| CN1968935A (en) * | 2004-06-18 | 2007-05-23 | 巴斯福股份公司 | 1-methyl-3-trifluoromethyl-pyrazole-4-carboxylic acid (ortho-phenyl)-anilides and to use thereof as fungicide |
| CN101115723A (en) * | 2005-02-16 | 2008-01-30 | 巴斯福股份公司 | Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi |
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2013
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| US4346097A (en) * | 1980-09-30 | 1982-08-24 | Warner-Lambert Company | Method for treating convulsions with pyrazole-4-carboxamide derivatives |
| CN1646494A (en) * | 2002-02-19 | 2005-07-27 | 拜尔农作物科学股份公司 | Disubstituted pyrazolyl carboxanilides |
| CN1871221A (en) * | 2003-10-23 | 2006-11-29 | 拜尔农作物科学股份公司 | N-substituted pyrazolyl carboxanilides |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106632044A (en) * | 2016-12-30 | 2017-05-10 | 浙江工业大学 | Amide compound containing methylpyrazole and preparation method the application thereof |
| CN107935929A (en) * | 2017-12-01 | 2018-04-20 | 浙江工业大学 | 3 trifluoromethyl 1H pyrazoles of a kind of 1 methyl, 4 amide derivatives and preparation method and application |
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| CN103554026B (en) | 2016-04-27 |
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