CN111747940B - Quinolinone semicarbazone derivative and preparation method and application thereof - Google Patents
Quinolinone semicarbazone derivative and preparation method and application thereof Download PDFInfo
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- CN111747940B CN111747940B CN202010652327.2A CN202010652327A CN111747940B CN 111747940 B CN111747940 B CN 111747940B CN 202010652327 A CN202010652327 A CN 202010652327A CN 111747940 B CN111747940 B CN 111747940B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 20
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- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 40
- 235000013311 vegetables Nutrition 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 14
- 230000007226 seed germination Effects 0.000 claims abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 239000011593 sulfur Chemical group 0.000 claims abstract description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 8
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Chemical group 0.000 claims abstract description 8
- 150000002367 halogens Chemical group 0.000 claims abstract description 8
- 229910052757 nitrogen Chemical group 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
- 239000000243 solution Substances 0.000 claims description 34
- 239000011259 mixed solution Substances 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 16
- 230000007935 neutral effect Effects 0.000 claims description 14
- 229940125782 compound 2 Drugs 0.000 claims description 13
- 229940125898 compound 5 Drugs 0.000 claims description 13
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 12
- 229930185107 quinolinone Natural products 0.000 claims description 12
- 239000002244 precipitate Substances 0.000 claims description 11
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 claims description 10
- 240000008384 Capsicum annuum var. annuum Species 0.000 claims description 10
- 240000008067 Cucumis sativus Species 0.000 claims description 10
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 claims description 10
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 10
- 240000003768 Solanum lycopersicum Species 0.000 claims description 10
- 241000254113 Tribolium castaneum Species 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- 240000008042 Zea mays Species 0.000 claims description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 9
- 235000005822 corn Nutrition 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 235000019441 ethanol Nutrition 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 239000005457 ice water Substances 0.000 claims description 8
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000741 silica gel Substances 0.000 claims description 8
- 229910002027 silica gel Inorganic materials 0.000 claims description 8
- OVYTZAASVAZITK-UHFFFAOYSA-M sodium;ethanol;hydroxide Chemical compound [OH-].[Na+].CCO OVYTZAASVAZITK-UHFFFAOYSA-M 0.000 claims description 8
- 239000008247 solid mixture Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 229940125904 compound 1 Drugs 0.000 claims description 7
- 229940126214 compound 3 Drugs 0.000 claims description 7
- 229940126062 Compound A Drugs 0.000 claims description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 6
- 239000001387 apium graveolens Substances 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- -1 methoxy, hydroxymethyl Chemical group 0.000 claims description 4
- 238000013375 chromatographic separation Methods 0.000 claims description 3
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- 230000035784 germination Effects 0.000 abstract description 13
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
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- 238000001819 mass spectrum Methods 0.000 description 10
- 230000000749 insecticidal effect Effects 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
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- USFUFHFQWXDVMH-UHFFFAOYSA-N 1-(1-methylindol-5-yl)-3-(3-methyl-1,2-thiazol-5-yl)urea Chemical compound S1N=C(C)C=C1NC(=O)NC1=CC=C(N(C)C=C2)C2=C1 USFUFHFQWXDVMH-UHFFFAOYSA-N 0.000 description 1
- GFBVUFQNHLUCPX-UHFFFAOYSA-N 5-bromothiophene-2-carbaldehyde Chemical compound BrC1=CC=C(C=O)S1 GFBVUFQNHLUCPX-UHFFFAOYSA-N 0.000 description 1
- VWYFITBWBRVBSW-UHFFFAOYSA-N 5-chlorothiophene-2-carbaldehyde Chemical compound ClC1=CC=C(C=O)S1 VWYFITBWBRVBSW-UHFFFAOYSA-N 0.000 description 1
- OUDFNZMQXZILJD-UHFFFAOYSA-N 5-methyl-2-furaldehyde Chemical compound CC1=CC=C(C=O)O1 OUDFNZMQXZILJD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
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- 239000003905 agrochemical Substances 0.000 description 1
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- 150000001408 amides Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
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- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
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- 229920000053 polysorbate 80 Polymers 0.000 description 1
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- 238000002791 soaking Methods 0.000 description 1
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Images
Classifications
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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 relates to the field of pesticides, in particular to a quinolinone semicarbazone derivative and a preparation method and application thereof. The invention solves the technical problem of providing a compound serving as an insecticide and a vegetable seed germination promoter. The structural formula of the compound is shown as formula I; wherein X is oxygen, sulfur or nitrogen; r is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 hydroxyalkyl or halogen. The compound has good poisoning effect on storage pests and good promotion effect on the germination of vegetable seeds.
Description
Technical Field
The invention relates to the field of pesticides, in particular to a quinolinone semicarbazone derivative and a preparation method and application thereof.
Background
The amide compounds have wide biological activity, including sterilization, antioxidation, plant growth regulation and the like. Therefore, extensive and intensive research on the compounds has been conducted over the past decades, and many novel and highly effective compounds have been discovered, and there have been continuously reported varieties which are novel in structure, unique in mode of action, excellent in performance, highly effective against harmful organisms, safe against non-target organisms, easily degradable in the environment, and safe in the human health and ecological environment as degradation products.
It is known that furan ring is an electron-rich system, which easily forms intermolecular hydrogen bonds with various biological enzymes, and thus some furan ring-containing compounds, both natural and synthetic, have a broad spectrum of biological activities, such as bacteriostasis, antivirus, antitumor, insecticidal, herbicidal, etc. Meanwhile, the compounds generally have the characteristics of high efficiency, low toxicity, safety to non-target organisms, easiness in degradation in the environment, difficulty in generation of resistance by pests and the like, so that the compounds containing furan rings play more and more important roles in the research and development processes of pesticides.
Thiophene is an important member of heterocyclic compounds and plays a very important role. The study of thiophene derivatives also has a very major role in medicine and agrochemical chemistry. Thiophene derivatives have a wide variety of biological activities, for example, antibacterial, antiviral, antitumor, anti-inflammatory, insecticidal, herbicidal, and the like. Meanwhile, the thiophene ring-containing compounds generally have the characteristics of high efficiency, low toxicity, safety to non-target organisms, easiness in degradation in the environment, difficulty in generation of resistance by pests and the like, and compounds with novel structures and excellent performance are continuously published. Therefore, in the process of research and development of pesticides, compounds containing thiophene rings will receive more extensive attention and become hot spots for creating new pesticides.
Until now, no report has been made on the use of quinolinone semicarbazone derivatives as pesticides and vegetable seed germination promoters.
Disclosure of Invention
The first technical problem solved by the invention is to provide a compound serving as an insecticide and a vegetable seed germination promoter.
The compound of the invention has a structural formula shown as a formula I:
wherein X is oxygen, sulfur or nitrogen; r is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 hydroxyalkyl or halogen.
In one embodiment, R is hydrogen, methyl, methoxy, hydroxymethyl, chloro, or bromo.
In one embodiment, R is hydrogen, methyl, chloro, or bromo.
In one embodiment, the X is oxygen or sulfur.
In one embodiment, the compound has the following structural formula:
the second technical problem solved by the invention is to provide a preparation method of the compound.
The preparation method of the compound comprises the following steps:
a. dissolving 2-aminoacetophenone in absolute ethyl alcohol, adding NaOH ethanol solution, adding a mixed solution of a compound A and the absolute ethyl alcohol, and reacting at 0-5 ℃;
b. after the reaction is finished, adjusting the pH value of the reaction solution to be neutral, then adding p-toluenesulfonic acid into the reaction solution, and reacting at 65-70 ℃;
c. after the reaction is finished, pouring the reaction liquid into ice water, adjusting the pH value of the solution to 7-9 by using triethylamine until a precipitate is separated out, filtering, washing the precipitate, and recrystallizing by using absolute ethyl alcohol to obtain a quinolinone intermediate;
d. dissolving the quinolinone intermediate in acetic acid, adding a mixed solution of semicarbazide and ethanol, reacting at 25-35 ℃, removing the solvent to obtain a solid mixture after the reaction is finished, and performing chromatographic separation on a silica gel column to obtain a target compound;
wherein the compound A is
Wherein X is oxygen, sulfur or nitrogen; r is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 hydroxyalkyl or halogen.
The invention also provides application of the compound in preparing a medicament for preventing and treating pests.
The compound of the invention has excellent insecticidal effect.
In one embodiment, the pest is a storage pest.
In one embodiment, the pest is elephant corn, clothes of grain or tribolium castaneum;
preferably, when the pest is a corn weevil, the compound is compound 1 or compound 5; when the pests are the clothes, the compound is compound 2 or compound 3; when the pest is tribolium castaneum, the compound is compound 4 or compound 5;
more preferably, when the pest is a corn elephant, the compound is compound 1; when the pest is tribolium castaneum, the compound is compound 5.
The invention also provides application of the compound in preparing a seed germination promoter.
Researches show that the compound can promote the germination of seeds and improve the germination rate of the seeds, and can be prepared into a seed germination promoter.
In one embodiment, the seed is a vegetable seed; in another embodiment, the vegetable seed is a cucumber seed, a green pepper seed, a tomato seed, or a celery seed;
preferably, when the vegetable seed is cucumber seed, the compound is compound 2 or compound 4; when the vegetable seed is a green pepper seed, the compound is compound 2 or compound 4; when the vegetable seed is a tomato seed, the compound is compound 3 or compound 5; when the vegetable seed is celery seed, the compound is compound 2 or compound 4.
The invention has the beneficial effects that:
according to the invention, amide skeleton and furan ring (or thiophene ring) are introduced into the molecular structure of quinolinone to synthesize some quinolinone semicarbazone derivatives, and some active compounds or active lead compounds with novel structures and excellent activity are found, so that the synthesis process is simple, the insecticidal composition has a good poisoning effect on storage pests, and has a good promotion effect on the germination of vegetable seeds, and a good foundation is laid for the creation of new pesticides.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of the compound of example 1.
FIG. 1-a is a detailed view of a nuclear magnetic hydrogen spectrum of the compound of example 1.
FIG. 2 is a nuclear magnetic carbon spectrum of the compound of example 1.
FIG. 3 is a high resolution mass spectrum of the compound of example 1.
FIG. 4 is a nuclear magnetic hydrogen spectrum of the compound of example 2.
FIG. 5 is a nuclear magnetic carbon spectrum of the compound of example 2.
FIG. 6 is a high resolution mass spectrum of the compound of example 2.
FIG. 7 is a nuclear magnetic hydrogen spectrum of the compound of example 3.
FIG. 8 is a nuclear magnetic carbon spectrum of the compound of example 3.
FIG. 9 is a high resolution mass spectrum of the compound of example 3.
FIG. 10 is a nuclear magnetic hydrogen spectrum of the compound of example 4.
FIG. 11 is a nuclear magnetic carbon spectrum of the compound of example 4.
FIG. 12 is a high resolution mass spectrum of the compound of example 4.
FIG. 13 is a nuclear magnetic hydrogen spectrum of the compound of example 5.
FIG. 14 is a nuclear magnetic carbon spectrum of the compound of example 5.
FIG. 15 is a high resolution mass spectrum of the compound of example 5.
Detailed Description
The first technical problem solved by the invention is to provide a compound serving as an insecticide and a vegetable seed germination promoter.
The compound of the invention has a structural formula shown as a formula I:
wherein X is oxygen, sulfur or nitrogen; r is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 hydroxyalkyl or halogen.
In one embodiment, R is hydrogen, methyl, methoxy, hydroxymethyl, chloro, or bromo.
In one embodiment, R is hydrogen, methyl, chloro, or bromo.
In one embodiment, the X is oxygen or sulfur.
In one embodiment, the compound has the following structural formula:
the second technical problem solved by the invention is to provide a preparation method of the compound.
The compound of the invention can be prepared by adopting a conventional chemical method.
In one embodiment, the following reaction procedure may be used.
Wherein X is oxygen, sulfur or nitrogen; r is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 hydroxyalkyl or halogen.
The preparation method of the compound specifically comprises the following steps:
a. dissolving 2-aminoacetophenone in absolute ethyl alcohol, adding NaOH ethanol solution, adding a mixed solution of a compound A and the absolute ethyl alcohol, and reacting at 0-5 ℃;
b. after the reaction is finished, adjusting the pH value of the reaction solution to be neutral, then adding p-toluenesulfonic acid into the reaction solution, and reacting at 65-70 ℃;
c. after the reaction is finished, pouring the reaction solution into ice water, adjusting the pH value of the solution to 7-9 by using triethylamine until a precipitate is separated out, filtering, washing the precipitate until washing water is neutral, and recrystallizing by using absolute ethyl alcohol to obtain a quinolinone intermediate;
d. dissolving the quinolinone intermediate in acetic acid, adding a mixed solution of semicarbazide and ethanol, reacting at 25-35 ℃, removing the solvent to obtain a solid mixture after the reaction is finished, and performing chromatographic separation on a silica gel column to obtain a target compound;
wherein the compound A is
Wherein X is oxygen, sulfur or nitrogen; r is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 hydroxyalkyl or halogen.
The invention also provides application of the compound in preparing a medicament for preventing and treating pests.
The compound of the invention has excellent insecticidal effect.
In one embodiment, the pest is a storage pest.
In one embodiment, the pest is elephant corn, clothes of grain or tribolium castaneum;
preferably, when the pest is a corn weevil, the compound is compound 1 or compound 5; when the pests are the clothes, the compound is compound 2 or compound 3; when the pest is tribolium castaneum, the compound is compound 4 or compound 5;
more preferably, when the pest is a corn elephant, the compound is compound 1; when the pest is tribolium castaneum, the compound is compound 5.
The invention also provides application of the compound in preparing a seed germination promoter.
Researches show that the compound can promote the germination of seeds and improve the germination rate of the seeds, and can be prepared into a seed germination promoter.
In one embodiment, the seed is a vegetable seed; in another embodiment, the vegetable seed is a cucumber seed, a green pepper seed, a tomato seed, or a celery seed;
preferably, when the vegetable seed is cucumber seed, the compound is compound 2 or compound 4; when the vegetable seed is a green pepper seed, the compound is compound 2 or compound 4; when the vegetable seed is a tomato seed, the compound is compound 3 or compound 5; when the vegetable seed is celery seed, the compound is compound 2 or compound 4.
The following examples are provided to further illustrate the embodiments of the present invention and are not intended to limit the scope of the present invention.
Example 1:
compound 1:
preparation of
0.01mol of 2-aminoacetophenone was dissolved in 10mL of anhydrous ethanol, and 10mL of 10% NaOH ethanol solution was added thereto. Stirring in an ice bath, slowly dropping a mixed solution of 0.01mol of furfural and 10mL of absolute ethyl alcohol into the mixed solution by using a constant-pressure dropping funnel, reacting at 0-5 ℃, and checking whether the reaction is finished by using a thin-layer silica gel plate (TLC). After the reaction was complete, the pH of the solution was adjusted to neutral with 10% HCl. Then, 0.01mol of p-toluenesulfonic acid is added into the reaction mixture, the reaction is carried out at 65-70 ℃, and the completion of the reaction is checked by TLC. And after the reaction is finished, pouring the reaction solution into 100mL of ice water, adjusting the pH value of the solution to 7-9 by using triethylamine, separating out a precipitate, filtering, washing with distilled water to be neutral, and recrystallizing with absolute ethyl alcohol to obtain a quinolinone intermediate.
0.01mol of the home-made intermediate was dissolved in 15mL of acetic acid. And slowly dropping a mixed solution of 0.02mol of semicarbazide and 15mL of 95% ethanol into the mixed solution by using a constant-pressure dropping funnel, reacting at 25-35 ℃, and checking whether the reaction is finished by using TLC. After the reaction is finished, removing the solvent by rotary evaporation to obtain a solid mixture, and separating by silica gel column chromatography (eluent is a mixture of ethyl acetate and petroleum ether with the volume ratio of 1: 50) to obtain the target compound, wherein the physical and chemical properties of the target compound are as follows:
a pale yellow plate crystal; the yield is 88%; the hydrogen spectrum is shown in figure 1, the carbon spectrum is shown in figure 2, the high resolution mass spectrum is shown in figure 3, and particularly,1HNMR(400MHz,DMSO-d6)δ(ppm):9.32(1H,s),7.96(1H,dd,J＝8.0,1.2Hz),7.61(1H,dd,J＝1.6,0.4Hz),7.07-7.03(1H,m),6.76(1H,dd,J＝8.0,0.8Hz),6.62-6.58(1H,m),6.47-6.44(3H,m),6.40(1H,dd,J＝3.2,2.0Hz),6.24(1H,d,J＝3.2Hz),4.51(1H,t,J＝6.4Hz),2.93(1H,dd,J＝16.8,5.2Hz),2.86(1H,dd,J＝16.4,8.0Hz)；13C NMR(100MHz,DMSO-d6)δ(ppm):157.89,155.67,146.82,142.66,141.16,130.06,124.93,118.56,117.70,116.00,110.82,106.65,47.94,29.56；HRMS(ESI)m/z:Calcd for C14H14N4O2[M+H]+:271.1190,Found:271.1193.
example 2:
compound 2:
preparation of
0.01mol of 2-aminoacetophenone was dissolved in 10mL of anhydrous ethanol, and 10mL of 10% NaOH ethanol solution was added thereto. Stirring in an ice bath, slowly dropping a mixed solution of 0.01mol of 5-methylfurfural and 10mL of absolute ethanol into the mixed solution by using a constant-pressure dropping funnel, reacting at 0-5 ℃, and checking whether the reaction is finished by using a thin-layer silica gel plate (TLC). After the reaction was complete, the pH of the solution was adjusted to neutral with 10% HCl. Then, 0.01mol of p-toluenesulfonic acid is added into the reaction mixture, the reaction is carried out at 65-70 ℃, and the completion of the reaction is checked by TLC. And after the reaction is finished, pouring the reaction solution into 100mL of ice water, adjusting the pH value of the solution to 7-9 by using triethylamine, separating out a precipitate, filtering, washing with distilled water to be neutral, and recrystallizing with absolute ethyl alcohol to obtain a quinolinone intermediate.
0.01mol of the home-made intermediate was dissolved in 15mL of acetic acid. And slowly dropping a mixed solution of 0.02mol of semicarbazide and 15mL of 95% ethanol into the mixed solution by using a constant-pressure dropping funnel, reacting at 25-35 ℃, and checking whether the reaction is finished by using TLC. After the reaction is finished, removing the solvent by rotary evaporation to obtain a solid mixture, and separating by silica gel column chromatography (eluent is a mixture of ethyl acetate and petroleum ether with the volume ratio of 1: 50) to obtain the target compound, wherein the physical and chemical properties of the target compound are as follows:
a light brown powder; the yield is 89%; the hydrogen spectrum is shown in fig. 4, the carbon spectrum is shown in fig. 5, the high resolution mass spectrum is shown in fig. 6, and particularly,1H NMR(400MHz,DMSO-d6)δ(ppm):9.30(1H,s),7.96(1H,d,J＝8.0Hz),7.06-7.02(1H,m),6.77(1H,d,J＝8.0Hz),6.61-6.57(1H,m),6.47(2H,s),6.38(1H,s),6.11(1H,d,J＝3.2Hz),6.00(1H,d,J＝2.0Hz),4.43(1H,dd,J＝8.0,4.4Hz),2.93(1H,dd,J＝16.8,4.4Hz),2.79(1H,dd,J＝16.8,8.8Hz),2.25(3H,s)；13C NMR(100MHz,DMSO-d6)δ(ppm):157.85,153.80,151.17,146.94,141.29,130.00,124.92,118.56,117.64,115.99,107.36,106.77,48.02,29.67,13.82；HRMS(ESI)m/z:Calcd for C15H16N4O2[M+H]+:285.1346,Found:285.1347.
example 3:
compound 3:
preparation of
0.01mol of 2-aminoacetophenone was dissolved in 10mL of anhydrous ethanol, and 10mL of 10% NaOH ethanol solution was added thereto. Stirring in an ice bath, slowly dropping a mixed solution of 0.01mol of thiophene-2-formaldehyde and 10mL of absolute ethyl alcohol into the mixed solution by using a constant-pressure dropping funnel, reacting at 0-5 ℃, and checking whether the reaction is finished by using a thin-layer silica gel plate (TLC). After the reaction was complete, the pH of the solution was adjusted to neutral with 10% HCl. Then, 0.01mol of p-toluenesulfonic acid is added into the reaction mixture, the reaction is carried out at 65-70 ℃, and the completion of the reaction is checked by TLC. And after the reaction is finished, pouring the reaction solution into 100mL of ice water, adjusting the pH value of the solution to 7-9 by using triethylamine, separating out a precipitate, filtering, washing with distilled water to be neutral, and recrystallizing with absolute ethyl alcohol to obtain a quinolinone intermediate.
0.01mol of the home-made intermediate was dissolved in 15mL of acetic acid. And slowly dropping a mixed solution of 0.02mol of semicarbazide and 15mL of 95% ethanol into the mixed solution by using a constant-pressure dropping funnel, reacting at 25-35 ℃, and checking whether the reaction is finished by using TLC. After the reaction is finished, removing the solvent by rotary evaporation to obtain a solid mixture, and separating by silica gel column chromatography (eluent is a mixture of ethyl acetate and petroleum ether with the volume ratio of 1: 50) to obtain the target compound, wherein the physical and chemical properties of the target compound are as follows:
a beige powder; yield: 83 percent; the hydrogen spectrum is shown in fig. 7, the carbon spectrum is shown in fig. 8, the high resolution mass spectrum is shown in fig. 9, and specifically,1H NMR(400MHz,DMSO-d6)δ(ppm):9.30(1H,s),7.98(1H,dd,J＝8.0,1.2Hz),7.43(1H,dd,J＝4.8,1.2Hz),7.10-7.05(2H,m),6.99(1H,dd,J＝4.8,3.2Hz),6.77(1H,d,J＝7.6Hz),6.64-6.60(1H,m),6.57(1H,s),6.46(2H,s),4.73(1H,dd,J＝9.2,4.4Hz),3.03(1H,dd,J＝16.4,4.4Hz),2.72(1H,dd,J＝16.4,9.2Hz)；13C NMR(100MHz,DMSO-d6)δ(ppm):157.83,147.41,147.00,141.22,130.06,127.06,125.24,125.11,124.97,118.71,117.85,116.14,50.44,33.88；HRMS(ESI)m/z:Calcd for C14H14N4OS[M+H]+:287.0961,Found:287.0950.
example 4:
compound 4:
preparation of
0.01mol of 2-aminoacetophenone was dissolved in 10mL of anhydrous ethanol, and 10mL of 10% NaOH ethanol solution was added thereto. Stirring in an ice bath, slowly dropping a mixed solution of 0.01mol of 5-chlorothiophene-2-formaldehyde and 10mL of absolute ethyl alcohol into the mixed solution by using a constant-pressure dropping funnel, reacting at 0-5 ℃, and checking whether the reaction is finished by using a thin-layer silica gel plate (TLC). After the reaction was complete, the pH of the solution was adjusted to neutral with 10% HCl. Then, 0.01mol of p-toluenesulfonic acid is added into the reaction mixture, the reaction is carried out at 65-70 ℃, and the completion of the reaction is checked by TLC. And after the reaction is finished, pouring the reaction solution into 100mL of ice water, adjusting the pH value of the solution to 7-9 by using triethylamine, separating out a precipitate, filtering, washing with distilled water to be neutral, and recrystallizing with absolute ethyl alcohol to obtain a quinolinone intermediate.
0.01mol of the home-made intermediate was dissolved in 15mL of acetic acid. And slowly dropping a mixed solution of 0.02mol of semicarbazide and 15mL of 95% ethanol into the mixed solution by using a constant-pressure dropping funnel, reacting at 25-35 ℃, and checking whether the reaction is finished by using TLC. After the reaction is finished, removing the solvent by rotary evaporation to obtain a solid mixture, and separating by silica gel column chromatography (eluent is a mixture of ethyl acetate and petroleum ether with the volume ratio of 1: 50) to obtain the target compound, wherein the physical and chemical properties of the target compound are as follows:
dark brown powder; the yield is 87%; the hydrogen spectrum is shown in fig. 10, the carbon spectrum is shown in fig. 11, the high resolution mass spectrum is shown in fig. 12, and specifically,1H NMR(400MHz,DMSO-d6)δ(ppm):9.32(1H,s),7.98(1H,d,J＝7.2Hz),7.10-7.05(1H,m),6.99(1H,d,J＝4.0Hz),6.95(1H,d,J＝4.0Hz),6.75(1H,d,J＝8.0Hz),6.64-6.61(2H,m),6.48(2H,s),4.70(1H,dd,J＝7.6,4.4Hz),2.99(1H,dd,J＝16.4,4.4Hz),2.75(1H,dd,J＝16.4,8.8Hz)；13C NMR(100MHz,DMSO-d6)δ(ppm):157.82,146.95,146.50,140.67,130.15,127.05,126.72,125.01,124.89,118.74,118.06,116.17,50.55,33.19；HRMS(ESI)m/z:Calcd for C14H13ClN4OS[M+H]+:321.0571,Found:321.0569.
example 5:
compound 5:
preparation of
0.01mol of 2-aminoacetophenone was dissolved in 10mL of anhydrous ethanol, and 10mL of 10% NaOH ethanol solution was added thereto. Stirring in an ice bath, slowly dropping a mixed solution of 0.01mol of 5-bromothiophene-2-formaldehyde and 10mL of absolute ethyl alcohol into the mixed solution by using a constant pressure dropping funnel, reacting at 0-5 ℃, and checking whether the reaction is finished by using a thin-layer silica gel plate (TLC). After the reaction was complete, the pH of the solution was adjusted to neutral with 10% HCl. Then, 0.01mol of p-toluenesulfonic acid is added into the reaction mixture, the reaction is carried out at 65-70 ℃, and the completion of the reaction is checked by TLC. And after the reaction is finished, pouring the reaction solution into 100mL of ice water, adjusting the pH value of the solution to 7-9 by using triethylamine, separating out a precipitate, filtering, washing with distilled water to be neutral, and recrystallizing with absolute ethyl alcohol to obtain a quinolinone intermediate.
0.01mol of the home-made intermediate was dissolved in 15mL of acetic acid. And slowly dropping a mixed solution of 0.02mol of semicarbazide and 15mL of 95% ethanol into the mixed solution by using a constant-pressure dropping funnel, reacting at 25-35 ℃, and checking whether the reaction is finished by using TLC. After the reaction is finished, removing the solvent by rotary evaporation to obtain a solid mixture, and separating by silica gel column chromatography (eluent is a mixture of ethyl acetate and petroleum ether with the volume ratio of 1: 50) to obtain the target compound, wherein the physical and chemical properties of the target compound are as follows:
a tan powder; the yield is 85 percent; the hydrogen spectrum is shown in fig. 13, the carbon spectrum is shown in fig. 14, the high-resolution mass spectrum is shown in fig. 15, and specifically,1H NMR(400MHz,DMSO-d6)δ(ppm):9.31(1H,s),7.97(1H,d,J＝8.0Hz),7.09(1H,d,J＝3.6Hz),7.07-7.05(1H,m),6.92(1H,d,J＝4.0Hz),6.74(1H,d,J＝8.0Hz),6.65(1H,s),6.62(1H,d,J＝7.2Hz),6.47(2H,s),4.72(1H,dd,J＝7.6,4.4Hz),2.97(1H,dd,J＝16.4,4.4Hz),2.75(1H,dd,J＝16.4,8.4Hz)；13C NMR(100MHz,DMSO-d6)δ(ppm):157.80,149.63,146.49,140.64,130.24,130.15,125.92,125.00,118.73,118.03,116.16,110.16,50.53,33.16；HRMS(ESI)m/z:Calcd for C14H13BrN4OS[M+H]+:365.0066,Found:365.0071.
experimental example 1: determination of insecticidal Activity of Compounds of the present invention
(1) Test pest
Adult corn weevils, adult corn clothes and adult tribolium castaneum, which are all sensitive strains bred indoors for years.
(2) Measurement method
Adopting a feed mixing method: mixing the compound to be tested and the wheat feed uniformly according to a certain dosage. Weighing 100 g of the drug-mixed feed into 500mL wide-mouth bottles, putting 30 heads of tested pests into each bottle, wrapping the bottle mouth with white cloth, placing the bottles in a pest feeding room with the temperature of 28-30 ℃ and the relative humidity of 70-80% for continuous feeding, and taking the feed without the drug as a blank control. Mortality was recorded after 14 days, each experiment was repeated 3 times, and corrected mortality was calculated using the following formula:
(3) results of the experiment
The insecticidal results of the compounds of the present invention are shown in table 1.
TABLE 1 poisoning Activity of Compounds of the invention against storage pests
a: average of three replicates.
From Table 1 above, it is clear that the compounds of the present invention have a good poisoning activity against these pests.
Experimental example 2: measurement of Germination-promoting Effect of the Compound of the present invention on vegetable seeds
(1) Test seeds
Cucumber seeds (Zhongnong No. 8), green pepper seeds (Fengyuan No. 8), tomato seeds (Dongfeng No. 4), and celery seeds (Jinnanshi No. 1).
(2) Measurement method
The test compounds were dissolved in dimethyl sulfoxide and diluted to 20mg/L in tap water containing 0.1% Tween-80 for use. 10 g of cucumber seeds, 10 g of green pepper seeds, 5 g of tomato seeds and 5 g of celery seeds are respectively weighed. And respectively soaking the test solution into 20mL of the test solution, stirring for 30 minutes, fishing out the test solution into a small sieve, washing for 3-4 times by using tap water, and air-drying for later use. The corresponding solution without test compound was used as a blank. 100 seeds with uniform size and no defect treated by the liquid medicine are respectively selected and are horizontally placed in a culture dish (9cm) paved with double-layer filter paper. The water adding amount for the 1 st time is as follows: 9mL of cucumber, 7mL of green pepper, 5mL of tomato and 5mL of celery are put into a constant temperature box (25 +/-2 ℃) for accelerating germination, observed for 1 time every day and quantitatively supplemented when water is deficient. Each treatment was repeated 3 times. The germination of cucumber was checked after 1 day, the germination of green pepper after 5 days, the germination of tomato after 3 days, and the germination of celery after 9 days, and the average germination percentage was calculated for 3 replicates.
(3) Results of the experiment
The germination-promoting effect of the compounds of the present invention on vegetable seeds is shown in table 2.
TABLE 2 accelerating effect of the compound of the present invention on seed germination at 20mg/L
a: average of three replicates.
As is clear from Table 2, the compounds of the present invention have a good accelerating effect on the germination of the seeds of all of the above 4 vegetables.
The foregoing embodiments are intended to illustrate that the invention may be implemented or used by those skilled in the art, and modifications to the above embodiments will be apparent to those skilled in the art, and therefore the invention includes, but is not limited to, the above embodiments, any methods, processes, products, etc., consistent with the principles and novel and inventive features disclosed herein, and fall within the scope of the invention.
Claims (15)
1. A compound of formula I:
wherein X is oxygen, sulfur or nitrogen; r is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 hydroxyalkyl or halogen.
2. A compound according to claim 1, wherein R is hydrogen, methyl, methoxy, hydroxymethyl, chloro or bromo.
3. A compound according to claim 1, wherein R is hydrogen, methyl, chloro or bromo.
4. The compound of claim 1, wherein X is oxygen or sulfur.
5. The compound of claim 1, having the formula:
6. a process for the preparation of a compound according to any one of claims 1 to 5, comprising the steps of:
a. dissolving 2-aminoacetophenone in absolute ethyl alcohol, adding NaOH ethanol solution, adding a mixed solution of a compound A and the absolute ethyl alcohol, and reacting at 0-5 ℃;
b. after the reaction is finished, adjusting the pH value of the reaction solution to be neutral, then adding p-toluenesulfonic acid into the reaction solution, and reacting at 65-70 ℃;
c. after the reaction is finished, pouring the reaction liquid into ice water, adjusting the pH value of the solution to 7-9 by using triethylamine until a precipitate is separated out, filtering, washing the precipitate, and recrystallizing by using absolute ethyl alcohol to obtain a quinolinone intermediate;
d. dissolving the quinolinone intermediate in acetic acid, adding a mixed solution of semicarbazide and ethanol, reacting at 25-35 ℃, removing the solvent to obtain a solid mixture after the reaction is finished, and performing chromatographic separation on a silica gel column to obtain a target compound;
wherein the compound A is
Wherein X is oxygen, sulfur or nitrogen; r is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 hydroxyalkyl or halogen.
7. Use of a compound according to any one of claims 1 to 5 for the preparation of a medicament for controlling pests.
8. The use of a compound according to claim 7 for the manufacture of a medicament for the control of pests, wherein said pests are stored-grain pests.
9. Use of a compound according to claim 7 for the preparation of a medicament for controlling pests, wherein the pests are elephants, clothes of the corn, or tribolium castaneum.
10. The use of a compound according to claim 5 for the manufacture of a medicament for controlling pests, wherein when the pest is a zeamais species, the compound is compound 1 or compound 5; when the pests are the clothes, the compound is compound 2 or compound 3; when the pest is tribolium castaneum, the compound is compound 4 or compound 5.
11. The use of a compound according to claim 10 for the manufacture of a medicament for controlling pests, wherein when the pest is a zeamais species, the compound is compound 1; when the pest is tribolium castaneum, the compound is compound 5.
12. Use of a compound according to any one of claims 1 to 5 for the preparation of a seed germination promoter.
13. Use of a compound according to claim 12 for the preparation of a seed germination promoter, wherein the seed is a vegetable seed.
14. Use of a compound according to claim 13 for the preparation of a seed germination promoter, wherein the vegetable seed is cucumber seed, green pepper seed, tomato seed or celery seed.
15. Use of a compound according to claim 5 for the preparation of a seed germination promoter, wherein when the vegetable seed is cucumber seed, the compound is compound 2 or compound 4; when the vegetable seed is a green pepper seed, the compound is compound 2 or compound 4; when the vegetable seed is a tomato seed, the compound is compound 3 or compound 5; when the vegetable seed is celery seed, the compound is compound 2 or compound 4.
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