CN113045562B - Thiazole compound for plant bacteriostasis and application thereof - Google Patents
Thiazole compound for plant bacteriostasis and application thereof Download PDFInfo
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- CN113045562B CN113045562B CN202110331547.XA CN202110331547A CN113045562B CN 113045562 B CN113045562 B CN 113045562B CN 202110331547 A CN202110331547 A CN 202110331547A CN 113045562 B CN113045562 B CN 113045562B
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- thiazole compound
- thiazole
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- 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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- 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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- 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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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
The invention relates to a thiazole compound with antibacterial property and application thereof in the technical field of medicinal chemistry, wherein the preparation method of the thiazole compound comprises the following steps: taking 2- (p-methylthio phenoxymethyl) -4- (N-isobutyl-aminomethyl) -thiazole and 2-thiophenecarbonyl chloride as raw materials, and taking CH2Cl2Triethylamine is used as a solvent, the reaction liquid is stirred for 10 to 14 hours at normal temperature while reacting, after the reaction, an organic layer is separated and purified, and finally the 2- (p-methylthiophenoxymethyl) -4- (N-isobutyl-N-2-thenoyl-aminomethyl) -thiazole compound is obtained. The thiazole compound can effectively inhibit the growth of various fungi, has obvious inhibition effect on wheat take-all pathogen, and is a novel antibacterial agent for preventing and treating plant fungi.
Description
Technical Field
The invention relates to the field of medicinal chemistry, in particular to thiazole compounds (I) containing amide structures and application thereof.
Background
Thiazole compounds generally have significant biological activity. In recent years, the biological activity of amide compounds is also paid more attention, and the unique biological activity of the amide compounds has the condition of creating green pesticides, and more researches show that the amide compounds have outstanding effects on the aspects of killing insects and bacteria, resisting cold, resisting stress and the like in agriculture.
Succinate dehydrogenase inhibitors (SDHIs) are agriculturally important commercial fungicides that exert inhibitory activity against phytopathogenic fungi by disrupting the tricarboxylic acid cycle and mitochondrial electron transport processes by competing for binding sites to coenzyme Q. The existing 23 SDHI bactericides are continuously marketed and comprise various structure types, such as pyrazole amides, benzamides, thiazole amides, thiophene amides, furan amides and the like. Because the bactericide has the characteristics of high bacteriostatic activity, novel action mechanism and more structural types, the development of the SDHI bactericide with a novel structure becomes a research hotspot.
Disclosure of Invention
The invention aims to provide a novel thiazole compound containing an amide structure, and the antibacterial effect of the novel thiazole compound is researched so as to develop a novel antibacterial agent applied to control of plant fungi.
In order to achieve the purpose, the invention provides a thiazole compound with antibacterial property, wherein the thiazole compound is 2- (p-methylthiophenoxymethyl) -4- (N-isobutyl-N-2-thiophenecarboxyl-aminomethyl) -thiazole, and the structural formula is shown as formula I:
further, the synthesis method of the thiazole compound comprises the following steps: takes 2- (p-methylthiophenoxymethyl) -4- (N-isobutyl-aminomethyl) -thiazole and 2-thiophenecarbonyl chloride as raw materials and CH2Cl2Using triethylamine as a solvent, reacting the reaction solution at normal temperature while stirring for 10-14 hours by using triethylamine as an acid-binding agent, separating and purifying an organic layer after the reaction, and finally obtaining the 2- (p-methylthio phenoxymethyl) -4- (N-isobutyl-N-2-thiophene formyl-aminomethyl) -thiazole compound, wherein the specific process comprises the following steps:
furthermore, the molar ratio of the 2- (p-methylthiophenoxymethyl) -4- (N-isobutyl-aminomethyl) -thiazole, the 2-thiophenecarbonyl chloride and the triethylamine is 1 (1-1.1): (0.5-1).
Further, the separated and purified organic layer is purified by adopting a column-layer separation column, and the volume ratio of a column-passing solvent is 1: (10-14) A mixed solution of ethyl acetate and petroleum ether.
Furthermore, the thiazole compound can effectively inhibit rice bakanae disease, cotton wilt disease, wheat take-all and rice sheath blight disease.
Furthermore, the thiazole compound has an obvious effect of inhibiting rhizoctonia solani.
The invention also aims to provide an antibacterial drug prepared by the thiazole compound, which is used for inhibiting various germs such as rice bakanae disease, cotton wilt disease, wheat take-all and rice sheath blight disease.
The thiazole compound of the present invention has the following advantageous effects:
1) the thiazole novel thiazole compound containing the amide structure is synthesized by one-step reaction, the synthesis method has mild conditions, and the reaction and post-treatment operations are simple, so that the synthesis method has certain popularization and application potentials;
2) the preparation method is simple in preparation route, and the raw materials and auxiliary materials participating in the reaction are simple and easy to obtain.
3) The target compound (I) obtained by the invention has an inhibiting effect on various plant fungi, and lays a solid foundation for the development of novel plant antibacterial agents.
Drawings
FIG. 1 is a drawing showing a preparation method of a thiazole compound obtained in example 11H-NMR spectrum.
FIG. 2 is a diagram of thiazole compounds prepared in example 113C-NMR spectrum.
Detailed Description
Example 1: preparation of thiazole Compounds
The compound 2- (p-methylthiophenoxymethyl) -4- (N-isobutyl-aminomethyl) -thiazole (1.61 g, 5 mmol), 10mL of dichloromethane and 1mL of triethylamine were sequentially added to a 50mL three-necked flask, and the mixture was magnetically stirred at room temperature to dissolve the compound. Then, dropwise adding a mixed solution of 2-thiophenecarboxyl chloride (0.77 g, 5.25 mmol) and 5 mL of dichloromethane at room temperature while stirring, finishing dropwise adding for about 20 min, then, continuously reacting for 12h while stirring at room temperature, after the reaction is completed, slowly pouring the reaction solution into ice water, separating out an organic phase, washing the organic phase to be neutral by using 5% sodium bicarbonate solution and water respectively, and spin-drying the organic phase to obtain a crude product, wherein the volume ratio of the crude product to the dichloromethane is 1: 12, using a mixed solution of ethyl acetate and petroleum ether as a column-passing solvent, and performing column-passing purification to obtain 1.72g of a target product of the thiazole compound, which is a light yellow solid and has a yield of 79.6%, wherein the structural formula of the product is shown as the following formula I:
the structure of the product is verified as follows:
the obtained product is detected and verified by an infrared spectrometer and is shown in figures 1 and 2; the nuclear magnetic resonance instrument has the following nuclear magnetic verification results:
1H NMR (400 MHz, DMSO-d 6) δ 7.75 (d, J = 5.0 Hz, 1H), 7.59 (br, 2H), 7.11 (d, J = 8.4 Hz, 3H), 6.95 (d, J = 8.5 Hz, 2H), 5.38 (s, 2H), 4.80 (s, 2H), 3.27 (br, 2H), 2.51 (t, J = 2.0 Hz, 1H), 2.24 (s, 3H), 2.08 – 1.93 (m, 1H), 0.82 (d, J = 7.0 Hz, 6H);
13C NMR (101 MHz, DMSO-d 6) δ 164.32, 155.88, 152.59, 138.51, 130.66, 130.36, 130.35, 129.91, 129.28, 127.52, 118.12, 115.24, 67.16, 53.26, 49.80, 26.70, 20.54, 20.31.
example 2 bacteriostatic assay for Compound I
In this example, the thiazole compound prepared in example 1 was used as an antibacterial active ingredient in a resistance test against phytopathogenic fungi such as Rhizoctonia solani, Fusarium oxysporum, Rhizoctonia cerealis, Rhizoctonia solani, and the respective strains were subjected to conventional subculture before use.
Preparing a PDA culture medium, sterilizing the culture medium and a culture dish, activating the strain, measuring the bacteriostatic activity of the thiazole compound by adopting a method for inhibiting the growth rate of hyphae, and calculating the inhibition rates of the thiazole compound with different concentrations on different plant pathogenic fungi in the test process, wherein the results are shown in Table 1.
TABLE 1 data on the inhibition of fungi by the target compounds
Experimental results show that the thiazole compound can inhibit the growth of various plant fungi, is optimal for rhizoctonia solani, and lays a solid foundation for the development of novel plant antibacterial agents.
Claims (7)
1. A thiazole compound for plant bacteriostasis is characterized in that the thiazole compound is 2- (p-methylthiophenoxymethyl) -4- (N-isobutyl-N-2-thiophenecarbonyl-aminomethyl) -thiazole, and the structural formula is shown as a formula I:
2. a thiazole compound for plant bacteriostasis according to claim 1, wherein the synthesis method of said thiazole compound is: taking 2- (p-methylthiophenoxymethyl) -4- (N-isobutyl-aminomethyl) -thiazole and 2-thiophenecarbonyl chloride as raw materials and CH2Cl2Using triethylamine as a solvent, taking triethylamine as an acid-binding agent to enable reaction liquid to be stirred and react for 10-14 hours at normal temperature, separating and purifying an organic layer after the reaction, and finally obtaining the 2- (p-methylthio phenoxymethyl) -4- (N-isobutyl-N-2-thiophene formyl-aminomethyl) -thiazole compound, wherein the specific process comprises the following steps:
3. a thiazole compound for plant bacteriostasis according to claim 2, wherein the molar ratio of 2- (p-methylthiophenoxymethyl) -4- (N-isobutyl-aminomethyl) -thiazole, 2-thiophenecarbonyl chloride and triethylamine is 1 (1-1.1): (0.5-1).
4. A thiazole compound for plant bacteriostasis according to claim 2, wherein the separated and purified organic layer is purified by column chromatography, and the volume ratio of the column-passing solvent is 1: (10-15) A mixed solution of ethyl acetate and petroleum ether.
5. A thiazole compound for plant bacteriostasis according to claim 2, wherein said thiazole compound is effective in inhibiting rice bakanae disease, cotton wilt disease, wheat take all and rice sheath blight disease.
6. A thiazole compound for plant bacteriostasis according to claim 2, wherein said thiazole compound has a significant inhibitory effect against Rhizoctonia solani.
7. A bacteriostatic agent prepared from the thiazole compound according to any one of claims 1 to 6, which is used for preparing a bacteriostatic agent comprising the thiazole compound and/or a hydrate thereof as an active ingredient.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159696A (en) * | 2011-12-15 | 2013-06-19 | 天津市嘉涵化工科技有限公司 | Preparation and bactericidal activity of N-phenyl-substituted thiazole methanamide compounds |
| CN104829605A (en) * | 2015-05-20 | 2015-08-12 | 贵州大学 | 1-substituted-5-trifluoromethyl-4-pyrazol-1,3,4-oxadiazole thioether or sulfone derivatives and application of derivatives |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159696A (en) * | 2011-12-15 | 2013-06-19 | 天津市嘉涵化工科技有限公司 | Preparation and bactericidal activity of N-phenyl-substituted thiazole methanamide compounds |
| CN104829605A (en) * | 2015-05-20 | 2015-08-12 | 贵州大学 | 1-substituted-5-trifluoromethyl-4-pyrazol-1,3,4-oxadiazole thioether or sulfone derivatives and application of derivatives |
Non-Patent Citations (2)
| Title |
|---|
| 2-(2-氨基噻唑-4-基)-(Z)-甲氧亚氨基乙酸酯的酰胺及亚胺衍生物的合成及抑菌活性;高涵莹等;《农药学学报》;20110615(第03期);全文 * |
| 新型含醚结构噻唑类化合物的合成及其抑菌活性;仇立干等;《合成化学》;20150320(第03期);全文 * |
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