CN115124462A - 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound and preparation method and application thereof - Google Patents
2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound and preparation method and application thereof Download PDFInfo
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- CN115124462A CN115124462A CN202210865872.9A CN202210865872A CN115124462A CN 115124462 A CN115124462 A CN 115124462A CN 202210865872 A CN202210865872 A CN 202210865872A CN 115124462 A CN115124462 A CN 115124462A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
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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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The invention discloses a 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound as well as a preparation method and application thereof, wherein the compound is prepared by reacting 2, 4-difluoroaniline with 2-methyl ethyl acetoacetate to prepare 2, 3-dimethyl-6, 8-difluoro-4-hydroxyquinoline, and then reacting the 2, 3-dimethyl-6, 8-difluoro-4-hydroxyquinoline with various chlorobenzyls to prepare the 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound. The preparation method is simple and convenient to operate, and 17 prepared compounds are prepared by 1 HNMR and HRMS characterization, and at 50ppm concentration for bactericidal activity test. The results show that: 16 compounds all have bactericidal activity, the inhibition rate of I-10 on sclerotinia sclerotiorum and rhizoctonia solani is more than 60%, and the inhibition rates of I-2 and I-4 on botrytis cinerea are 63% respectively3% and 60.0%.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis and drug application, and particularly relates to a 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound and a preparation method and application thereof.
Background
Food and environmental issues remain a major issue in today's world. The breadth of our country is broad, and the country is a big country of population and agriculture from the ancient times, and the agricultural production has no significance to our country. In the development of heterocyclic pesticides, the compound plays an important role in the development of novel pesticides. Quinoline is a common and very important nitrogen-containing heterocyclic structure, extracted from coal tar by Runge in 1834. Many heterocyclic compounds containing quinoline structure have very important biological and pharmacological activities, and thus, of course, become the most common in the creation of new pesticides.
In recent years, synthesis of various quinoline compounds has been reported, and many compounds containing quinoline structures are put on the market as commercial pesticides. Moreover, the structural modification of known natural products or commercial compounds to develop safe pesticides with higher activity and lower toxicity has been a hot spot of research direction of agricultural chemists.
Disclosure of Invention
The invention aims to provide a 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound and a preparation method and application thereof, wherein the invention takes Tebufloquin as a lead compound, keeps the quinoline ring of the Tebufloquin and the methyl of the 2, 3-position on the ring unchanged, replaces tert-butyl with fluoro, modifies the ester bond part, introduces ether bond, and synthesizes a series of 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compounds.
The invention discloses a 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound, which has a structural formula shown in a formula (I):
in the formula (I), R is alkyl, phenyl, substituted phenyl, benzoyl, substituted benzoyl, cyano or 2-chlorothiazol-5-yl, the substituent of the substituted phenyl is alkyl or halogen, and the substituent of the substituted benzoyl is halogen, alkoxy or substituted alkyl; preferably, the substituents of the substituted phenyl are 2-chloro, 4-bromo, 2-fluoro, 4-fluoro, 2-methyl, 2, 4-dichloro, 3-fluoro; the substituent of the substituted benzoyl is 4-bromine, 4-methoxyl, 4-chlorine, 4-fluorine and 4-trifluoromethyl.
Furthermore, the invention also discloses a preparation method of the 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound, which comprises the following steps;
1) reacting 2, 4-difluoroaniline with 2-methyl ethyl acetoacetate by using polyphosphoric acid as a cyclizing agent to generate a compound shown as a formula (II);
2) taking DMF as a solvent, and stirring the compound shown in the formula (II) obtained in the step 1) and the compound shown in the formula (III) at room temperature to react under the alkaline environment provided by NaH to obtain a 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound shown in the formula (I);
in the formula (I), R is alkyl, phenyl, substituted phenyl, benzoyl, substituted benzoyl, cyano or 2-chlorothiazol-5-yl, the substituent of the substituted phenyl is alkyl or halogen, and the substituent of the substituted benzoyl is halogen, alkoxy or substituted alkyl; preferably, the substituents of the substituted phenyl are 2-chloro, 4-bromo, 2-fluoro, 4-fluoro, 2-methyl, 2, 4-dichloro, 3-fluoro; the substituent of the substituted benzoyl is 4-bromine, 4-methoxyl, 4-chlorine, 4-fluorine and 4-trifluoromethyl.
The reaction process is as follows:
further, when the compound represented by the formula (II) is synthesized in the step 1), the mass ratio of the 2, 4-difluoroaniline to the ethyl 2-methylacetoacetate is 1:1-1:1.5, preferably 1:1.
Further, when the 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound is synthesized in the step 2), the mass ratio of the compound shown in the formula (II) to the compound shown in the formula (III) is 1:1-1:1.4, preferably 1: 1.1.
Further, when the 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound is synthesized in the step 2), the mass ratio of the compound shown as the formula (II) to NaH is 1:1-1:1.5, preferably 1: 1.3.
Furthermore, the invention also discloses application of the 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound in preparation of bactericides.
The invention has the beneficial effects that:
the preparation method is simple and convenient to operate, and the structure of the obtained product is shown in the specification 1 H NMR and HRMS were confirmed and the 17 target products obtained were tested for bactericidal activity, indicating: all compounds have certain antibacterial activity, and in the 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compounds, the inhibition rate of the compound I-14 on the tomato early blight bacteria is 41.7%; the inhibition rates of the compounds I-2, I-3 and I-10 on the wheat scab bacteria respectively reach 54.2 percent, 58.3 percent and 50.0 percent, and the inhibition rates of the compounds I-4 and I-8 reach 45.8 percent; the inhibition rates of the compounds I-4, I-10 and I-16 on rice blast germs are all up to more than 40.0 percent; the inhibition rate of the compound I-10 on phytophthora capsici reaches 58.1%, and the inhibition rate of the compound I-14 reaches 41.9%; the inhibition rates of the compounds I-2, I-8 and I-16 on sclerotinia sclerotiorum are respectively up to 50.0 percent, the inhibition rates of the compounds I-10 and I-1 are up to 66.7 percent and 41.7 percent; the inhibition rates of the compounds I-2 and I-4 to cucumber botrytis cinerea are respectively 63.3% and 60.0%, and the inhibition rates of the compounds I-10 and I-13 reach 50.0%; the inhibition rate of the compound I-10 on rice sheath blight bacteria reaches 63.6 percent, and the inhibition rates of the compounds I-5, I-8 and I-16 reach 45.5 percent; the inhibition rate of the compound I-8 on cucumber fusarium wilt bacteria reaches 47.6 percent; the inhibition rate of the compounds I-8 and I-9 on the ring rot of apple reaches 57.7 percent.
Detailed Description
The present invention is further illustrated by the following examples, which should not be construed as limiting the scope of the invention.
EXAMPLE 1 preparation of the Compound of formula (II)
A100 mL three-necked flask was charged with 2, 4-difluoroaniline (5.16g,40.00mmol), ethyl 2-methylacetoacetate (5.77g,40.00mmol) and polyphosphoric acid (20.28g,60.00mmol) in this order, and the reaction mixture was heated and stirred at 150 ℃ to carry out TLC (V) EA /V PE 1/1), stopping the reaction after 5h, cooling to room temperature, and placing the reaction flask into the reaction flaskIn ice bath, adjusting the pH value to 7-8 by using a 10% sodium hydroxide aqueous solution, separating out a large amount of solids, performing suction filtration, taking a filter cake, and drying to obtain a compound shown as a formula (II), wherein the compound is a white solid, and the yield is as follows: 83.2%, melting point: 241 to 243 ℃.
Example 2 preparation of a Compound of formula (I)
A17-mL 50-mL round-bottomed flask was charged with the compound represented by the formula (II) (0.20g,0.96mmol) prepared in example 1, sodium hydride (0.03g,1.25mmol) and DMF (10mL) in this order, and after stirring at room temperature for 0.5h, the compound represented by the formula (III) (1.06mmol) was added, followed by stirring and TLC (V) EA /V PE 1/4), transferring to separating funnel, adding water (30mL), extracting with ethyl acetate (10mL × 3), combining organic phases, washing with saturated brine (10mL × 3), drying with anhydrous sodium sulfate, filtering, spin-drying solvent, and column chromatography (mobile phase V) EA /V PE 1/4) to obtain the target compounds I-1 to I-17, and the specific data are shown in tables 1 and 2.
TABLE 12 physicochemical data of 3, 3-dimethyl-6, 8-difluoroquinolin-4-ether compounds
TABLE 22, 3-dimethyl-6, 8-difluoroquinolin-4-ethers 1 H NMR and HRMS data
Example 3 bactericidal Activity test
Test method
(1) Test subjects: early blight of tomato (Alternaria solani), Gibberella zeae (Gibberella zeae), Pyricularia oryzae (Pyricularia Grisea), Phytophthora capsici (Phytophtora capsici), Sclerotinia sclerotiorum (Sclerotinia sclerotiorum), Botrytis cinerea (Botrytis cinerea), Rhizoctonia solani (Riziocotinia solani), Fusarium oxysporum (Fusarium oxysporum), Pseudocercospora arachidicola (Cercospora arachidicola), and Phyllospora mallotoides (Physalospora piricola).
(2) Each test compound was dissolved in DMSO to 1% EC stock solution for use. And evaluating the indoor bactericidal activity of the compound to be tested on the test target at the dose of 50ppm by adopting a bacteriostatic ring method, and additionally setting a clear water control (QCK).
(3) The test method comprises the following steps: 150 microliter of the prepared EC mother liquor is absorbed by a pipette gun and dissolved in 2.85mL of Tween water to prepare a liquid medicine with the effective concentration of the compound to be detected being 500 ppm. Sucking 1ml of the liquid medicine by using a pipette gun, putting the liquid medicine into a sterilized culture dish, putting 9ml of PDA culture medium into the culture dish, shaking up, and cooling. And (3) beating the round bacterial cake by using a puncher, picking the round bacterial cake to the center of a culture dish by using an inoculating needle, then placing the culture dish in an incubator at 27 ℃ for culture, and measuring the diameter of a bacterial colony after 48 hours. The pure growth amount of the bacterial colony is the difference value between the average diameter of the bacterial colony and the diameter of the bacterial cake, and the calculation method of the bacteriostasis rate (%) refers to the following formula.
The results of the activity test are shown in table 3:
TABLE 32, 3-dimethyl-6, 8-difluoroquinolin-4-ether bactericidal activity
17 compounds of 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether all show certain bactericidal activity, and the inhibition rate of the compound I-14 on the tomato early blight bacteria is 41.7%; the inhibition rates of the compounds I-2, I-3 and I-10 on the wheat scab bacteria respectively reach 54.2 percent, 58.3 percent and 50.0 percent, and the inhibition rates of the compounds I-4 and I-8 reach 45.8 percent; the inhibition rates of the compounds I-4, I-10 and I-16 on rice blast germs are all up to more than 40.0 percent; the inhibition rate of the compound I-10 on phytophthora capsici reaches 58.1%, and the inhibition rate of the compound I-14 reaches 41.9%; the inhibition rates of the compounds I-2, I-8 and I-16 on sclerotinia sclerotiorum are respectively up to 50.0 percent, the inhibition rates of the compounds I-10 and I-1 are up to 66.7 percent and 41.7 percent; the inhibition rates of the compounds I-2 and I-4 to cucumber botrytis cinerea are respectively 63.3% and 60.0%, and the inhibition rates of the compounds I-10 and I-13 reach 50.0%; the inhibition rate of the compound I-10 on rice sheath blight bacteria reaches 63.6 percent, and the inhibition rates of the compounds I-5, I-8 and I-16 reach 45.5 percent; the inhibition rate of the compound I-8 on cucumber fusarium wilt bacteria reaches 47.6 percent; the inhibition rate of the compounds I-8 and I-9 on the ring rot of apple reaches 57.7 percent.
The description is given for the sole purpose of illustrating embodiments of the inventive concept and should not be taken as limiting the scope of the invention to the particular forms set forth in the embodiments, but rather as being limited only to the equivalents thereof as may be contemplated by those skilled in the art based on the teachings herein.
Claims (8)
- A2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound is characterized in that the structural formula is shown as the formula (I):
in the formula (I), a substituent R is alkyl, phenyl, substituted phenyl, benzoyl, substituted benzoyl, cyano or 2-chlorothiazol-5-yl, a substituent on the substituted phenyl is alkyl or halogen, and a substituent on the substituted benzoyl is halogen, alkoxy or substituted alkyl. - 2. The 2, 3-dimethyl-6, 8-difluoroquinolin-4-ether compound of claim 1 wherein the substituent on the substituted phenyl is 2-chloro, 4-bromo, 2-fluoro, 4-fluoro, 2-methyl, 2, 4-dichloro, 3, 4-dichloro, or 3-fluoro.
- 3. The 2, 3-dimethyl-6, 8-difluoroquinolin-4-ether compound of claim 1 or 2 wherein the substituent on the substituted benzoyl group is 4-bromo, 4-methoxy, 4-chloro, 4-fluoro, 4-trifluoromethyl.
- 4. A process for preparing 2, 3-dimethyl-6, 8-difluoroquinolin-4-ether compounds as claimed in claim 1, comprising the steps of;1) reacting 2, 4-difluoroaniline with 2-methyl ethyl acetoacetate by using polyphosphoric acid as a cyclizing agent to generate a compound shown as a formula (II);2) taking DMF as a solvent, and stirring the compound shown in the formula (II) obtained in the step 1) and the compound shown in the formula (III) at room temperature to react under the alkaline environment provided by NaH to obtain a 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compound shown in the formula (I);
in the formula (I) and the formula (III), a substituent R is alkyl, phenyl, substituted phenyl, benzoyl, substituted benzoyl, cyano or 2-chlorothiazole-5-yl, a substituent on the substituted phenyl is alkyl or halogen, and a substituent on the substituted benzoyl is halogen, alkoxy or substituted alkyl. - 5. The method for producing 2, 3-dimethyl-6, 8-difluoroquinolin-4-ether compounds according to claim 4, wherein the amount of 2, 4-difluoroaniline to ethyl 2-methylacetoacetate is 1:1 to 1:1.5, when the compound represented by the formula (II) is synthesized in the step 1).
- 6. The method for producing 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compounds according to claim 4, wherein the mass ratio of the compound represented by the formula (II) to the compound represented by the formula (III) is 1:1 to 1:1.4 when the 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compounds are synthesized in the step 2).
- 7. The method for producing 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compounds according to claim 4, wherein the mass ratio of the compound represented by the formula (II) to NaH is 1:1 to 1:1.5 when the 2, 3-dimethyl-6, 8-difluoroquinoline-4-ether compounds are synthesized in the step 2).
- 8. The use of the 2, 3-dimethyl-6, 8-difluoroquinolin-4-ether compound of claim 1 in the preparation of a bactericide.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1034924A (en) * | 1988-01-29 | 1989-08-23 | 伊莱利利公司 | quinoline, quinazoline and cinnoline derivatives |
| CN1893949A (en) * | 2003-12-24 | 2007-01-10 | 默克专利有限公司 | Acidic quinoline derivatives and their use for the prevention and/or treatment of hyperglycaemia-related pathologies |
| CN101426486A (en) * | 2005-12-01 | 2009-05-06 | 先灵公司 | Compounds for the treatment of inflammatory disorders and microbial diseases |
| CN109320452A (en) * | 2017-07-31 | 2019-02-12 | 东莞东阳光科研发有限公司 | Quinoline derivatives and its preparation method and application |
-
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- 2022-07-22 CN CN202210865872.9A patent/CN115124462B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1034924A (en) * | 1988-01-29 | 1989-08-23 | 伊莱利利公司 | quinoline, quinazoline and cinnoline derivatives |
| CN1893949A (en) * | 2003-12-24 | 2007-01-10 | 默克专利有限公司 | Acidic quinoline derivatives and their use for the prevention and/or treatment of hyperglycaemia-related pathologies |
| CN101426486A (en) * | 2005-12-01 | 2009-05-06 | 先灵公司 | Compounds for the treatment of inflammatory disorders and microbial diseases |
| CN109320452A (en) * | 2017-07-31 | 2019-02-12 | 东莞东阳光科研发有限公司 | Quinoline derivatives and its preparation method and application |
Non-Patent Citations (1)
| Title |
|---|
| 范文玉，等: "2,3-二甲基喹啉类化合物的合成及其生物活性" * |
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