CN104610155A - Preparation method for imazalil - Google Patents
Preparation method for imazalil Download PDFInfo
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- CN104610155A CN104610155A CN201510061742.XA CN201510061742A CN104610155A CN 104610155 A CN104610155 A CN 104610155A CN 201510061742 A CN201510061742 A CN 201510061742A CN 104610155 A CN104610155 A CN 104610155A
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- imazalil
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- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000005795 Imazalil Substances 0.000 title claims abstract description 32
- 229960002125 enilconazole Drugs 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 18
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000002608 ionic liquid Substances 0.000 claims abstract description 13
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 150000002460 imidazoles Chemical class 0.000 claims description 19
- WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical class CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 claims description 16
- 239000010410 layer Substances 0.000 claims description 16
- 239000012044 organic layer Substances 0.000 claims description 16
- -1 tetrafluoroborate Chemical compound 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 8
- 238000013517 stratification Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000005580 one pot reaction Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- SOGLGKRIVMZMSK-UHFFFAOYSA-N 2-chloro-1-(2-chlorophenyl)ethanone Chemical compound ClCC(=O)C1=CC=CC=C1Cl SOGLGKRIVMZMSK-UHFFFAOYSA-N 0.000 description 2
- 241000234295 Musa Species 0.000 description 2
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 1
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 1
- XWRFNYYGDNIMII-UHFFFAOYSA-N C(C)C(=O)CC.ClC1=CC=CC(=C1)Cl Chemical compound C(C)C(=O)CC.ClC1=CC=CC(=C1)Cl XWRFNYYGDNIMII-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000021038 drupes Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a preparation method for imazalil. The method is characterized by adding 2,4-dichloro-2'-chlorophenylethanol, imidazole, allyl chloride, sodium carbonate and ionic liquid in a reaction container, reacting for 1-10 hours at 10-100 DEG C, and carrying out posttreatment to obtain the imazalil, wherein the ionic liquid is 1-methyl-3-alkyl imidazole tetrafluoroborate. According to the method, the imazalil is prepared by using the 2,4-dichloro-2'-chlorophenylethanol, imidazole and allyl chloride and adopting a one-pot reaction technology in an ionic liquid reaction system. The technology is green chemical preparation technology which is simple to operate, energy saving and emission reducing, environmentally friendly and recyclable.
Description
Technical field
The present invention relates to a kind of novel processing step of imazalil.
Background technology
Imazalil is that imidazoles sterilant is inhaled in a kind of has a broad antifungal spectrum of exploitation in 1973 by Belgian Yang Sen company.Not only there is preventive effect to many fungal diseases of invasion and attack fruit, vegetables and ornamental crops, especially citrus, banana and other fruit sprayed, flood rotten (being mainly used in the storage of apple, banana, Cauliflower) that can prevent and treat the rear gourd, fruit and vegetable of results, and have high activity to Helminthosporium, fusarium, Septoria and drupe leaf rust etc., can be used for preventing and treating cereal disease and seed treatment.At present, the chemosynthesis bibliographical information of imazalil is little.Chemical name is 1-[2-(2,4 dichloro benzene base)-2-(2-allyloxy) ethyl]-1 H-imidazoles, and molecular weight is 297.2, and structural formula is:
。
The synthesis of imazalil mainly contains two lines.Route one is that carbonyl reduction becomes hydroxyl by the methyl bromide of 2,4 dichloro benzene ethyl ketone, and then the nitrogen-atoms of bromo methylene radical and imidazoles replaces, last and allyl bromide 98 alkylated reaction; Route two is that 1,3-dichlorobenzene and chloro-acetyl chloride react the chloro-2 '-chloroacetophenone of generation 2,4-bis-, and carbonyl reduction is hydroxyl, carries out the alkylation of nitrogen-atoms with imidazoles, finally carries out the alkylated reaction on Sauerstoffatom with chlorallylene again.Route one is more in the side reaction of this step of reduction reaction, affects reaction yield; The chemically reactive of route dimethyl chloride is lower, not easily carries out the alkylated reaction of nitrogen-atoms with imidazoles.The chloro-2 '-chloroacetophenone of reaction raw materials 2,4-bis-is relatively active in addition, stability is bad and to be not easy to use by suitability for industrialized production, and the condition preparing this raw material is harsh, expensive reagents, and has strong impulse smell, and toxicity is also very large.Because fungi produces resistance to multi-medicament, and have the trend day by day increased, antifungal drug research is subject to the attention of global medicine scholar day by day.The superiority that imidazoles and triazole compound show in clinical application, makes it have wide application prospect.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of novel syntheti c route of imazalil, and this preparation method adopts the chloro-2 '-chlorinated benzene ethanol of 2,4-bis-, imidazoles and chlorallylene to be raw material, in ionic liquid, adopts one pot reaction technology to prepare imazalil.
For solving above technical problem, the preparation method of imazalil of the present invention, adds 2 in reaction vessel, the chloro-2 '-chlorinated benzene ethanol of 4-bis-, imidazoles, chlorallylene, sodium carbonate and ionic liquid, at 10 ~ 100 DEG C of temperature, react 1 ~ 10 hour, obtain imazalil through aftertreatment;
Described ionic liquid is 1-methyl-3-alkylimidazolium tetrafluoroborate.
Reaction formula of the present invention is as follows:
。
Further, the molar ratio of described 2,4-bis-chloro-2 '-chlorinated benzene ethanol and imidazoles and chlorallylene is 1:1 ~ 1.5: 1 ~ 1.5.
Again further, the molar ratio of described 2,4-bis-chloro-2 '-chlorinated benzene ethanol and imidazoles and chlorallylene is 1:1.2: 1.2.
Further, the alkyl in described ionic liquid is C
1~ C
10alkyl.
Further, the weight consumption of described ionic liquid is 3 ~ 8 times of 2,4-bis-chloro-2 '-chlorinated benzene ethanol weight.
Further, the temperature of reaction of described method is 50 ~ 80 DEG C.
Further, the reaction times of described method is 3 ~ 5 hours.
Further, described aftertreatment is that reaction terminates rear temperature of reaction and drops to room temperature, adds the water with reaction system roughly same volume; Stratification, separates aqueous layer and organic layer; Aqueous layer extracted with diethyl ether, merges all organic layers, dry, steams solvent and obtains imazalil product.It is >=99% that gained imazalil analyzes content through HPLC, fusing point 50 ~ 52 DEG C.
The present invention utilizes the chloro-2 '-chlorinated benzene ethanol of 2,4-bis-, imidazoles and chlorallylene, in ionic liquid reaction system, adopts one pot reaction technology to prepare imazalil.This technology is easy and simple to handle, energy-saving and emission-reduction, environmental friendliness and the Green Chemistry technology of preparing of reusable edible.
Embodiment
With specific embodiment, technical scheme of the present invention is described below, but protection scope of the present invention is not limited thereto:
embodiment 1
In 500 milliliters of there-necked flasks, add 2 successively, the chloro-2 '-chlorinated benzene ethanol of 4-bis-22.6 grams (0.1 mole), imidazoles 8.2 grams (0.12 mole), chlorallylene 9.2 grams (0.12 mole), 21 grams, sodium carbonate (0.2 mole) and 1-methyl-3-butyl imidazole tetrafluoroborate ion liquid 113 grams, under 50 DEG C of conditions, react 5 hours.After reaction terminates, temperature of reaction drops to room temperature, adds 174 grams of water, stratification, separates aqueous layer and organic layer, and aqueous layer 100 milliliters of extracted with diethyl ether 3 times, merge all organic layers, and drying, boils off solvent, obtain imazalil product 17.8 grams, yield 60%.It is >=99% that HPLC analyzes content.Fusing point 51 ~ 52 DEG C.
embodiment 2
In 500 milliliters of there-necked flasks, add 2 successively, the chloro-2 '-chlorinated benzene ethanol of 4-bis-22.6 grams (0.1 mole), imidazoles 6.8 grams (0.1 mole), chlorallylene 7.7 grams (0.1 mole), 21 grams, sodium carbonate (0.2 mole) and 1-methyl-3-octylimidazole tetrafluoroborate ion liquid 69 grams, under 80 DEG C of conditions, react 10 hours.After reaction terminates, temperature of reaction drops to room temperature, adds 128 grams of water, stratification, separates aqueous layer and organic layer, and aqueous layer 100 milliliters of extracted with diethyl ether 3 times, merge all organic layers, and drying, boils off solvent, obtain imazalil product 17.5 grams, yield 59%.It is >=99% that HPLC analyzes content.Fusing point 51 ~ 52 DEG C.
embodiment 3
In 500 milliliters of there-necked flasks, add 2 successively, the chloro-2 '-chlorinated benzene ethanol of 4-bis-22.6 grams (0.1 mole), imidazoles 10.2 grams (0.15 mole), chlorallylene 9.2 grams (0.12 mole), 21 grams, sodium carbonate (0.2 mole) and 1-methyl-3-benzyl imidazole tetrafluoroborate ion liquid 180 grams, under 100 DEG C of conditions, react 1 hour.After reaction terminates, temperature of reaction drops to room temperature, adds 243 grams of water, stratification, separates aqueous layer and organic layer, and aqueous layer 100 milliliters of extracted with diethyl ether 3 times, merge all organic layers, and drying, boils off solvent, obtain imazalil product 18.1 grams, yield 61%.It is >=99% that HPLC analyzes content.Fusing point 51 ~ 52 DEG C.
embodiment 4
In 500 milliliters of there-necked flasks, add 2 successively, the chloro-2 '-chlorinated benzene ethanol of 4-bis-22.6 grams (0.1 mole), imidazoles 8.2 grams (0.12 mole), chlorallylene 9.2 grams (0.12 mole), 1-methyl-3-octylimidazole tetrafluoroborate ion liquid 163 grams is 7 by sodium carbonate regulation system pH value, under 80 DEG C of conditions, react 8 hours.After reaction terminates, temperature of reaction drops to room temperature, adds 224 grams of water, stratification, separates aqueous layer and organic layer, and aqueous layer 100 milliliters of extracted with diethyl ether 3 times, merge all organic layers, and drying, boils off solvent, obtain imazalil product 17.8 grams, yield 60%.It is >=99% that HPLC analyzes content.Fusing point 51 ~ 52 DEG C.
embodiment 5
In 500 milliliters of there-necked flasks, add 2 successively, the chloro-2 '-chlorinated benzene ethanol of 4-bis-22.6 grams (0.1 mole), imidazoles 8.2 grams (0.12 mole), chlorallylene 9.2 grams (0.12 mole), 21 grams, sodium carbonate (0.2 mole) and 1-methyl-3-hexyl imidazolium tetrafluoroborate ion liquid 136 grams, under 40 DEG C of conditions, react 3 hours.After reaction terminates, temperature of reaction drops to room temperature, adds 200 grams of water, stratification, separates aqueous layer and organic layer, and aqueous layer 100 milliliters of extracted with diethyl ether 3 times, merge all organic layers, and drying, boils off solvent, obtain imazalil product 17.8 grams, yield 60%.It is >=99% that HPLC analyzes content.Fusing point 51 ~ 53 DEG C.
embodiment 6
In 500 milliliters of there-necked flasks, add 2 successively, the chloro-2 '-chlorinated benzene ethanol of 4-bis-22.6 grams (0.1 mole), imidazoles 8.2 grams (0.12 mole), chlorallylene 9.2 grams (0.12 mole), 21 grams, sodium carbonate (0.2 mole) and 1-methyl-3-butyl imidazole tetrafluoroborate ion liquid 160 grams, under 50 DEG C of conditions, react 6 hours.After reaction terminates, temperature of reaction drops to room temperature, adds 221 grams of water, stratification, separates aqueous layer and organic layer, and solution layer 100 milliliters of extracted with diethyl ether 3 times, merge all organic layers, and drying, boils off solvent, obtain imazalil product 18.4 grams, yield 62%.It is >=99% that HPLC analyzes content.Fusing point 51 ~ 52 DEG C.
Above-mentioned embodiment is exemplary, being to better enable those skilled in the art understand the present invention, can not being interpreted as it is limiting the scope of the invention; As long as any equivalent change done by disclosed spirit or modification, all fall into the scope of protection of the invention.
Claims (8)
1. a preparation method for imazalil, is characterized in that in reaction vessel, add the chloro-2 '-chlorinated benzene ethanol of 2,4-bis-, imidazoles, chlorallylene, sodium carbonate and ionic liquid, at 10 ~ 100 DEG C of temperature, reacts 1 ~ 10 hour, obtains imazalil through aftertreatment;
Described ionic liquid is 1-methyl-3-alkylimidazolium tetrafluoroborate.
2. the preparation method of imazalil according to claim 1, is characterized in that the molar ratio of described 2,4-bis-chloro-2 '-chlorinated benzene ethanol and imidazoles and chlorallylene is 1:1 ~ 1.5: 1 ~ 1.5.
3. the preparation method of imazalil according to claim 1, is characterized in that the molar ratio of described 2,4-bis-chloro-2 '-chlorinated benzene ethanol and imidazoles and chlorallylene is 1:1.2: 1.2.
4. the preparation method of imazalil according to claim 1, is characterized in that the alkyl in described ionic liquid is C
1~ C
10alkyl.
5. the preparation method of the imazalil according to claim 1 or 4, is characterized in that the weight consumption of described ionic liquid is 3 ~ 8 times of 2,4-bis-chloro-2 '-chlorinated benzene ethanol weight.
6. the preparation method of imazalil according to claim 1, is characterized in that the temperature of reaction of described method is 50 ~ 80 DEG C.
7. the preparation method of imazalil according to claim 1, is characterized in that the reaction times of described method is 3 ~ 5 hours.
8. the preparation method of imazalil according to claim 1, is characterized in that described aftertreatment is that reaction terminates rear temperature of reaction and drops to room temperature, adds the water with reaction system roughly same volume; Stratification, separates aqueous layer and organic layer; Aqueous layer extracted with diethyl ether, merges organic layer, dry, steams solvent and obtains imazalil product.
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104876873A (en) * | 2015-05-22 | 2015-09-02 | 池州中瑞化工有限公司 | Synthetic method of enilconazole |
| CN110437154A (en) * | 2019-09-10 | 2019-11-12 | 武汉川泰科技有限公司 | A kind of preparation method of enilconazole bulk pharmaceutical chemicals |
| CN110845416A (en) * | 2019-11-19 | 2020-02-28 | 武汉回盛生物科技股份有限公司 | O-allylation method of α -diaryl substituted ethanol |
| CN111187216A (en) * | 2020-03-23 | 2020-05-22 | 徐州工业职业技术学院 | Method for synthesizing imidazole ethanol by continuous method |
| CN111789120A (en) * | 2020-07-29 | 2020-10-20 | 湖南省植物保护研究所 | Bactericide imazalil ionic liquid, and preparation method and application thereof |
| CN115028586A (en) * | 2022-06-27 | 2022-09-09 | 池州中瑞化工有限公司 | Preparation method of chiral (S) -imazalil |
| CN115433132A (en) * | 2022-10-20 | 2022-12-06 | 武汉回盛生物科技股份有限公司 | A kind of enconazole crystal form, preparation method and application |
| CN116082245A (en) * | 2022-12-26 | 2023-05-09 | 武汉工程大学 | Enconazole crystal and preparation method and application thereof |
| CN116606255A (en) * | 2023-05-18 | 2023-08-18 | 上海农帆生物科技有限公司 | Preparation method of imazalil |
| CN118792003A (en) * | 2024-09-14 | 2024-10-18 | 江苏斯瑞达材料技术股份有限公司 | Polyurethane/epoxy resin thermosetting insulating adhesive and preparation method thereof |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104876873A (en) * | 2015-05-22 | 2015-09-02 | 池州中瑞化工有限公司 | Synthetic method of enilconazole |
| CN110437154A (en) * | 2019-09-10 | 2019-11-12 | 武汉川泰科技有限公司 | A kind of preparation method of enilconazole bulk pharmaceutical chemicals |
| CN110845416A (en) * | 2019-11-19 | 2020-02-28 | 武汉回盛生物科技股份有限公司 | O-allylation method of α -diaryl substituted ethanol |
| CN111187216A (en) * | 2020-03-23 | 2020-05-22 | 徐州工业职业技术学院 | Method for synthesizing imidazole ethanol by continuous method |
| CN111789120A (en) * | 2020-07-29 | 2020-10-20 | 湖南省植物保护研究所 | Bactericide imazalil ionic liquid, and preparation method and application thereof |
| CN111789120B (en) * | 2020-07-29 | 2022-04-01 | 湖南省植物保护研究所 | Bactericide imazalil ionic liquid, and preparation method and application thereof |
| CN115028586A (en) * | 2022-06-27 | 2022-09-09 | 池州中瑞化工有限公司 | Preparation method of chiral (S) -imazalil |
| CN115433132A (en) * | 2022-10-20 | 2022-12-06 | 武汉回盛生物科技股份有限公司 | A kind of enconazole crystal form, preparation method and application |
| CN116082245A (en) * | 2022-12-26 | 2023-05-09 | 武汉工程大学 | Enconazole crystal and preparation method and application thereof |
| CN116606255A (en) * | 2023-05-18 | 2023-08-18 | 上海农帆生物科技有限公司 | Preparation method of imazalil |
| CN118792003A (en) * | 2024-09-14 | 2024-10-18 | 江苏斯瑞达材料技术股份有限公司 | Polyurethane/epoxy resin thermosetting insulating adhesive and preparation method thereof |
| CN118792003B (en) * | 2024-09-14 | 2025-02-11 | 江苏斯瑞达材料技术股份有限公司 | Polyurethane/epoxy resin thermosetting insulating adhesive and preparation method thereof |
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Application publication date: 20150513 |