CN116730852A - Substituted phenyl isopropanolamine-containing compound, and preparation method and application thereof - Google Patents

Substituted phenyl isopropanolamine-containing compound, and preparation method and application thereof Download PDF

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CN116730852A
CN116730852A CN202310702493.2A CN202310702493A CN116730852A CN 116730852 A CN116730852 A CN 116730852A CN 202310702493 A CN202310702493 A CN 202310702493A CN 116730852 A CN116730852 A CN 116730852A
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China
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canker
compound
isopropanolamine
substituted phenyl
bacterial
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王培义
胡洪晟
孙蓓蕾
李长转
赵海聪
曾皖丽
廖来香
梁宇宇
慕江淇
叶豪杰
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Guizhou University
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Guizhou University
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    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
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    • C07C217/34—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
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    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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Abstract

The application relates to a compound containing substituted phenyl isopropanolamine, a preparation method and application thereof. The compound has a structure shown in a general formula (I):

Description

Substituted phenyl isopropanolamine-containing compound, and preparation method and application thereof
Technical Field
The application relates to the technical field of pharmaceutical chemistry, in particular to a compound containing substituted phenyl isopropanolamine, and a preparation method and application thereof.
Background
Plant bacterial diseases are one of the main factors affecting global agricultural production, seriously affect the yield and quality of agricultural products, cause great economic loss and threaten human health. Such as bacterial leaf blight of rice, canker of citrus, canker of kiwi fruit, bacterial wilt of tobacco and the like, outbreaks to different degrees each year, and causes huge economic loss for farmers. The long-term use of traditional bactericides such as thiabendazole, metconazole, streptomycin sulfate and the like not only increases the drug resistance of plant pathogenic bacteria, but also has harmful effects on the ecological environment and the safety of plants. Therefore, there is an urgent need to develop a novel pesticide having high activity and high selectivity.
In order to find an active compound with high-efficiency sterilization, the application takes substituted phenyl as a parent ring, connects propylene oxide, and then uses amine compounds to open the ring to obtain a target compound with isopropanolamine structure, synthesizes a series of compounds with novel structure and substituted phenyl isopropanolamine, tests the biological activity of the compounds, and provides an important scientific basis for the research and development and the creation of new pesticides.
The study of the biological activity of the substituted phenyl compounds proceeds as follows:
in 2019, zhao et al [ Zhao, yong Liang; huang, xing; liu, li Wei; wang, pei Yi; long, qing Su; tao, qing; li, zhong; yang, song. Identification of Racemic and Chiral Carbazole Derivatives Containing an Isopropanolamine Linker as Prospective Surrogates against Plant Pathogenic Bacteria: in Vitro and In Vivo Assays and Quantitative Proteomics [ J].J.Agric.Food Chem.，2019，67(26)，7512-7525.]The design and synthesis of the raceme chiral carbazole derivatives show that the compound 26 can obviously inhibit the growth of rice bacterial blight bacteria, citrus canker bacteria and kiwi fruit canker bacteria of plant pathogenic bacteria to be tested and the EC thereof 50 The values are 2.04, 2.42 and 0.603 mug/mL respectively, which is significantly better than the existing commercial medicines. In vivo studies prove that they have application prospects in the aspect of controlling plant bacterial diseases. Label-free quantitative proteomic analysis showed that compound 27 could significantly induce up-and down-regulation of 247 differentially expressed proteins, and this result was further confirmed by parallel reaction monitoring techniques.
In 2019, xiang et al [ Xiang, meng; zhou, xiang; luo, ting Rong; wang, pei Yi; liu, li Wei; li, zhong; wu, zhi big; yang, song. Design, synthesis, antibacterial Evaluation, and Induced Apoptotic Behaviors of Epimeric andChiral 18β-Glycyrrhetinic Acid Ester Derivatives with an Isopropanolamine Bridge against Phytopathogens[J].J.Agric.Food Chem.，2019，67(48)，13212-13220.]a series of 18 beta-glycyrrhetinic acid ester derivatives with different tertiary amines are designed and synthesized, and the pharmacological activity of the 18 beta-glycyrrhetinic acid ester derivatives is screened. The results showed that compounds 28, 29 were effective against plant pathogens Xanthomonas oryzae and Xanthomonas citri (EC) 50 3.81 and 2.76 mug/mL respectively) are superior to GA (EC) 50 > 400 μg/mL), thiabendazole and metconazole. Pharmacophore studies have shown that the synergistic combination of the GA backbone with tertiary amine scaffolds contributes to biological effects. In vivo experiments show their application prospects in controlling bacterial infections. The antibacterial mechanism research shows that the title compound can induce apoptosis of the tested pathogen, and the observed bacterial morphology change in the scanning electron microscope image is obvious. This result will facilitate the development of various apoptosis inducers.
In 2020, liu et al [ Liu, hong Wu; ji, qing Tian; ren, gang; wang, fang; su, fen; wang, pei Yi; zhou, xiang; wu, zhi big; li, zhong; an array of novel THC derivatives of 1,3-Diaminopropan-2-ol were prepared by Yang, song.antibacterial Functions and Proposed Modes of Action of Novel 1,2,3,4-tetrahydroβ -carboline Derivatives that Possess an Attractive, 3-diaminoprop-2-ol Pattern against Rice Bacterial Blight, kiwifruit Bacterial Canker, and Citrus Bacterial Canker [ J ]. J.agric.food chem.,2020, 68 (45), 12558-12568 ], and evaluated for biological activity, target compound 30 was used for three plant pathogens: the bacterial leaf blight bacteria, the citrus canker bacteria and the kiwi fruit canker bacteria all show excellent activity. . The relevant EC50 values were 1.69, 4.05 and 2.39. Mu.g/mL, respectively. The effect is better than that of the parent structure 1,2,3,4-THC and positive control. The antibacterial mechanism shows that tetrahydrocannabinol compounds can induce the increase of active oxygen of bacteria, so that the bacteria have obvious apoptosis behaviors. In addition, compound 30 may reduce hypersensitivity and pathogenicity of kiwifruit canker pathogens.
2021, huang et al [ Huang, xing; liu, hong Wu; long, zhou Qing; li, zhen Xing; zhu, jian Jun; wang, pei Yi; qi, pu Ying; liu, li Wei; 1,2,3-Triazole custom carbazole was prepared by Yang, song.RationalOptimation of 1,2,3-Triazole-Tailored Carbazoles As Prospective Antibacterial Alternatives with Significant In Vivo Control Efficiency and Unique Mode of Action [ J ]. J.Agric.Food chem.,2021, 69 (16), 4615-4627 ]. The compounds have inhibition effect on the growth of bacterial leaf blight bacteria, citrus canker bacteria and kiwifruit canker bacteria of rice, and EC50 values are respectively 3.36 (31), 2.87 (31) and 4.57 mug/mL (32). The potting test results show that the control effect of the compound 31 on the bacterial leaf blight of rice at the concentration of 200 mug/mL is 53.23% and 50.78% respectively. Interestingly, the addition of 0.1% of adjuvants such as organosilicon and orange oil can significantly improve the surface wettability of the compound 31 on rice leaves, and the control effect is respectively improved by 65.50% and 61.38%. Meanwhile, the compound 32 has obvious inhibition effect on white suppurative secretion caused by kiwi fruit canker pathogen infection, and the control effect of the compound is 79.42 percent (protective activity) and 78.74 percent (therapeutic activity) respectively at the concentration of 200 mug/mL, which is obviously better than that of the commercial pesticide thiabendazole copper.
Disclosure of Invention
The application provides a compound containing substituted phenyl isopropanolamine or a stereoisomer thereof or a salt thereof or a solvate thereof.
It is another object of the present application to provide an intermediate compound for preparing the above compound or a stereoisomer thereof, or a salt thereof or a solvate thereof, and a method for preparing the same.
It is still another object of the present application to provide a composition comprising the above compound or a stereoisomer thereof, or a salt thereof or a solvate thereof.
It is a further object of the present application to provide the use of the above compound or a stereoisomer thereof, or a salt thereof or a solvate thereof, or the composition.
It is another object of the present application to provide a method for controlling agricultural pests using the above-mentioned compound or a stereoisomer thereof, or a salt thereof or a solvate thereof, or the composition.
In order to achieve the above purpose, the present application adopts the following technical scheme:
a compound containing substituted phenyl isopropanolamine or a stereoisomer thereof, or a salt thereof or a solvate thereof, the compound having a structure as shown in a general formula (I):
wherein R is 1 、R 2 And R is 3 Each independently selected from hydrogen and chlorine; r is R 4 、R 5 Each independently selected from one or more of hydrogen, optionally substituted or unsubstituted alkyl, amino, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl;
the application also provides a preparation method of the compound containing the substituted phenyl isopropanolamine or the stereoisomer thereof, or the salt or the solvate thereof, which comprises the following steps:
the term "alkyl" as used herein is intended to include both branched and straight chain saturated hydrocarbon groups having a specified number of carbon atoms. For example "C 1-10 Alkyl "(or alkylene) is intended to mean C1, C2, C3, C4, C5, C6, C7, C8, C9 and C10 alkyl. In addition, e.g. "C 1-6 Alkyl "means an alkyl group having 1 to 6 carbon atoms. Alkyl groups may be unsubstituted or substituted such that one or more of its hydrogen atoms is replaced by another chemical group. Examples of alkyl groups include, but are not limited to, methyl (Me), ethyl (Et), propyl (e.g., n-propyl and isopropyl), butyl (e.g., n-butyl, isobutyl, t-butyl), pentyl (e.g., n-pentyl, isopentyl, neopentyl) and the like.
The term "substituted" as used herein refers to any one or more hydrogen atoms on a specified atom or group being replaced with a selected specified group, provided that the specified atom's general valency is not exceeded. Substituents are named to the central structure, unless otherwise indicated. For example, it is understood that when (cycloalkyl) alkyl is the possible substituent, the point of attachment of the substituent to the central structure is in the alkyl moiety. As used herein, a ring double bond is a double bond formed between two adjacent ring atoms (e.g., c= C, C =n or n=n). When referring to substitution, particularly polysubstituted, it is meant that a plurality of substituents are substituted at various positions on the indicated group, such as dichlorobenzyl refers to 2, 3-dichlorobenzyl, 2, 4-dichlorobenzyl, 2, 5-dichlorobenzyl, 2, 6-dichlorobenzyl, 3, 4-dichlorobenzyl and 3, 5-dichlorobenzyl.
Combinations of substituents and variables are permissible only if such combinations result in stable compounds or useful synthetic intermediates. The stable compound or stable structure implies that the compound is sufficiently stable when isolated from the reaction mixture in useful purity, and is formulated to form an effective therapeutic agent.
The term "heteroaryl" refers to substituted and unsubstituted aromatic 5-or 6-membered monocyclic groups, 9-or 10-membered bicyclic groups, and 11 to 14-membered tricyclic groups, having at least one heteroatom (O, S or N) in at least one ring, said heteroatom-containing ring preferably having 1,2 or 3 heteroatoms selected from O, S and N. Each ring of the heteroatom-containing heteroaryl group may contain one or two oxygen or sulfur atoms and/or from 1 to 4 nitrogen atoms provided that the total number of heteroatoms in each ring is 4 or less and that each ring has at least one carbon atom. The fused ring completing the bicyclic and tricyclic groups may contain only carbon atoms and may be saturated, partially saturated, or unsaturated. The nitrogen may optionally be oxidized and quaternized. Bicyclic or tricyclic heteroaryl groups must include at least one wholly aromatic ring and the nitrogen other fused rings may be aromatic or non-aromatic. Heteroaryl groups may be attached at any available nitrogen or carbon atom of any ring.
Exemplary monocyclic heteroaryl groups include pyrrolyl, pyrazolyl, pyrazolinyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, furanyl, thienyl, oxadiazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, and the like.
The compounds of the present application are understood to include both the free form and salts thereof, unless otherwise indicated. The term "salt" means an acid and/or base salt formed from inorganic and/or organic acids and bases. In addition, the term "salt" may include zwitterionic (inner salts), such as when the compounds of formula I contain basic moieties such as amine or pyridine or imidazole rings, and acidic moieties such as carboxylic acids. Pharmaceutically acceptable (i.e., non-toxic, physiologically acceptable) salts are preferred, such as acceptable metal and amine salts, wherein the cation does not contribute significantly to the toxicity or bioactivity of the salt. However, other salts may be useful, such as by employing isolation or purification steps in the preparation process, and are therefore also included within the scope of the present application.
Preferably C 1 -C 10 Alkyl refers to methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl and isomers thereof;
when referring to substituents as alkynyl, alkyl, aryl, benzyl, or where these substituents are specifically a particular alkynyl, alkyl, aryl, benzyl, cycloalkyl, one to three of the above substituents are meant. For example chlorobenzyl refers to one to three chloro-substituted benzyl groups.
By adopting the technical scheme, the application takes the substituted phenyl as the starting material to synthesize a series of compounds containing the substituted phenyl isopropanolamine, and the compounds are found to have good inhibition effect on pathogenic bacteria of pathogenic plants, have good inhibition effect on pathogenic bacteria [ such as bacterial leaf blight bacteria (Xanthomonas oryzae pv. Oryzae, xoo), citrus canker (Xanthomonas axonopodis pv. Citri, xac) and kiwi fruit canker (Pseudomonas syringae pv. Actinidiae, psa) and the like ], and have good inhibition effect on pathogenic fungi [ such as Botrytis cinerea, rhizoctonia solani and the like ], and provide important scientific basis for research and development and creation of new pesticides.
Examples
The application is further illustrated by the following examples. It should be understood that the methods described in the examples of the present application are only for illustrating the present application, and not for limiting the present application, and that simple modifications to the preparation methods of the present application under the concept of the present application are within the scope of the present application as claimed. All the starting materials and solvents used in the examples are commercially available products.
Example 1: preparation of intermediate 2- (2-chlorophenoxy) methyl oxirane
2-chlorophenol (15.56 mmol) and K 2 CO 3 (18.67 mmol) was added to a 100mL round bottom flask, 20mL DMF was added thereto, stirred at 60℃for 15 minutes, then epibromohydrin (23.34 mmol) was slowly added dropwise to the system, and the reaction was stopped after 5 hours; ethyl acetate (60 mL) was added, followed by saturated NH 4 Aqueous Cl (3X 30 mL) was washed, and the organic phase was collected over anhydrous Na 2 SO 4 Drying, desolventizing, column chromatography (PE: ea=10:1, V/V) gave a colorless liquid in 87.74% yield. The nuclear magnetic data are as follows: 1 H NMR(400MHz，CDCl 3 )δ7.36(dd，J＝1.6Hz，1H，phenyl-H)，7.22-7.18(m，1H，phenyl-H)，6.96-6.89(m，2H，phenyl-H)，4.29(dd，J＝2.8Hz，1H，phenyl-O-CH 2 -)，4.05(dd，J＝5.6Hz，1H，phenyl-O-CH2-)，3.41-3.37(m，1H，-O-CH-)，2.93-2.90(t，J＝4.8Hz，1H，-O-CH 2 -)，2.83(dd，J＝2.8Hz，1H，-O-CH 2 -). 13 C NMR(101MHz，CDCl 3 )δ154.1，130.5，127.8，123.2，122.2，114.0，69.7，50.2，44.8.
example 2: preparation of intermediate 4- (3- (2-chlorophenoxy) -2-hydroxypropyl) -1-tert-butoxycarbonyl piperazine
2- (2-chlorophenoxy) methyl oxirane (2.71 mmol) and K 2 CO 3 (18.67 mmol) was dissolved in 4mL of isopropanol solution, then 1-t-butoxycarbonyl piperazine (2.98 mmol) was added and reacted at 60 ℃. The TCL tracks the reaction until completion. Dichloromethane (20 mL) was added, washed with water (3×15 mL), and the organic phase was collected over anhydrous Na 2 SO 4 Drying, desolventizing, column chromatography (DCM: m=50:1, V/V) gave a yellow oil in 96.15% yield. The nuclear magnetic data are as follows: 1 H NMR(400MHz，CDCl 3 )δ7.33(dd，J＝7.9，1.6Hz，1H，phenyl-H)，7.19(ddd，J＝8.3，7.6，1.6Hz，1H，phenyl-H)，6.93(dd，J＝8.3，1.2Hz，1H，phenyl-H)，6.89(td，J＝7.7，1.3Hz，1H，phenyl-H)，4.14(td，J＝9.3，4.7Hz，1H，-O-CH-)，4.04(d，J＝4.9Hz，2H，-CH-CH 2 -piperazinyl)，3.46-3.40(m，4H，piperazinyl-H)，2.64-2.55(m，4H，piperazinyl-H)，2.45-2.37(m，2H，phenyl-O-CH 2 -)，1.44(s，9H，-C(CH 3 ) 3 ). 13 C NMR(101MHz，CDCl 3 )δ154.8，154.3，130.3，127.8，123.1，121.9，113.9，79.8，71.3，65.8，60.7，53.3，28.5，25.4.
example 3: preparation of intermediate 1- (2-chlorophenoxy) -3- (piperazin-1-yl) propanol
4- (3- (2-chlorophenoxy) -2-hydroxypropyl) -1-t-butoxycarbonylpiperazine (5.39 mmol) was dissolved in 10mL DCM and put into a 50mL round bottom flask, concentrated hydrochloric acid (5.39 mmol) was slowly added dropwise to the reaction system and stirred at room temperature for 2h. TLC tracing, desolventizing after completion of the reaction, adding 10mL of water, then K 2 CO 3 Adjusting pH to 9-10, and desolventizing to obtain yellow solid with a yield of 95.88%. The nuclear magnetic data are as follows: 1 H NMR(400MHz，CDCl 3 )δ7.35(dd，J＝7.9，1.5Hz，1H，phenyl-H)，7.22-7.17(m，1H，phenyl-H)，6.95(dd，J＝8.3，1.2Hz，1H，phenyl-H)，6.93-6.86(m，1H，phenyl-H)，4.17-4.10(m，1H，-O-CH-)，4.04(d，J＝5.0Hz，2H，-CH-CH 2 -piperazinyl)，3.03-2.77(m，4H，piperazinyl-H)，2.74-2.64(m，2H，piperazinyl-H)，2.61-2.57(m，2H，phenyl-O-CH 2 -)，2.49-2.37(m，2H，piperazinyl-H). 13 C NMR(101MHz，CDCl 3 )δ154.4，130.4，127.8，123.2，121.9，113.9，71.6，65.5，61.2，51.6，46.2.
example 4: preparation of the target Compound 3,3' -Ethylazadiylbis (1- (2-chlorophenoxy) propan-2-ol)
2- (2-chlorophenoxy) methyl oxirane (1.62 mmol) and K 2 CO 3 (0.81 mmol) was dissolved in 4mL of isopropanol solution, then ethylamine (0.81 mmol) was added and reacted at 60 ℃. The TCL tracks the reaction until completion. Quench the reaction with water (15 mL) followed by CH 2 Cl 2 (30 mL) extraction, washing with water (2X 30 mL), and washing the organic phase with anhydrous Na 2 SO 4 After drying, desolventizing and column chromatography (DCM: m=60:1, V/V) gave a white solid in 79 yield.28％。
Example 5: a target compound: 1- (2-chlorophenoxy) -3- (4- (3-trifluoromethylphenyl) piperazin-1-yl) propanol 1- (2-chlorophenoxy) -3- (piperazin-1-yl) propanol (1.11 mmol) and Cs 2 CO 3 (1.33 mmol) was dissolved in 4mL of DMSO solution, then 2-chloro-6-trifluoromethylpyridine (1.11 mmol) was added and reacted at 105 ℃. TCL followed the reaction until completion, then extracted with ethyl acetate (30 mL), washed with water (4X 15 mL), and the organic phase was washed with anhydrous Na 2 SO 4 After drying, desolventizing and column chromatography (DCM: m=100:1, V/V) gave a white solid in 53.17% yield.
Other target compounds were synthesized using the corresponding starting materials or substituents, with reference to the procedure of the examples described above.
The structure and nuclear magnetic resonance hydrogen spectrum and carbon spectrum data of the synthesized compound containing the substituted phenyl isopropanolamine are shown in table 1, and the physical and chemical properties are shown in table 2.
TABLE 1 Nuclear magnetic resonance Hydrogen Spectroscopy and carbon Spectroscopy data for the Compounds of the application
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TABLE 2 physicochemical Properties of the Compounds of the application
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Pharmacological example 1:
EC 50 (median effective concentration) is an important index for evaluating the sensitivity of plant pathogenic bacteria to a compound, and is also an important parameter for setting the concentration of the compound when researching the action mechanism of the target compound. In the concentration gradient experiment, proper 5 concentrations are set by adopting a double dilution method, and finally the inhibition rate of the medicament to plant pathogenic bacteria and the medicament concentration are converted into logarithmic values, and the virulence curve is obtained by SPSS software regression analysis, so that EC is calculated 50 。
By using turbid materialsMethod for testing effective medium concentration EC of target compound on plant pathogenic bacteria 50 The test subjects were rice bacterial leaf blight bacteria (Xoo), citrus canker bacteria (Xac) and kiwi fruit canker bacteria (Psa). DMSO was dissolved in the medium as a blank. Putting rice bacterial leaf blight bacteria (rice bacterial leaf blight pathogenic bacteria are in an M210 solid culture medium) into an NB culture medium, and carrying out shake culture in a constant-temperature shaking table at 28 ℃ and 180rpm until the bacterial leaf blight bacteria are in a logarithmic growth phase for later use; the citrus canker fungus (on M210 solid medium) is placed in NB medium and shake-cultured in a thermostatic shaker at 28℃and 180rpm until logarithmic growth phase is ready for use. 5mL of toxic NB liquid culture medium with different concentrations (for example, 100, 50, 25 and 12.5,6.25 mug/mL) of the medicament (compound) is added into a test tube, 40 mu L of NB liquid culture medium containing phytopathogenic bacteria is respectively added, and the culture is oscillated in a constant temperature shaking table at 28 ℃ and 180rpm, so that the rice bacterial leaf blight pathogenic bacteria are cultured for 36h, the citrus canker bacteria are cultured for 48h and the kiwi fruit canker bacteria are cultured for 36h. Measuring OD of bacterial solutions with various concentrations on a spectrophotometer 595 Values, and additionally determining the OD of corresponding concentrations of toxic sterile NB liquid medium 595 Values.
Corrected OD = bacteria-containing medium OD-sterile medium OD
Inhibition ratio = [ (corrected control culture medium bacterial liquid OD value-corrected toxic culture medium OD value)/corrected control culture medium bacterial liquid OD value ] ×100
The present application is described with the aid of examples, but the contents of examples are not limited thereto, and the experimental results of the target compounds are shown in table 3.
TABLE 3 inhibitory Activity of the Compounds of the application against phytopathogenic bacteria
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TABLE 4 EC of the compounds of the application against phytopathogenic bacteria 50
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"NT" means not tested
As can be seen from Table 4, the target compounds showed good inhibitory activity against plant pathogenic bacteria (such as Rhizoctonia solani, rhizoctonia cerealis and Rhizoctonia cerealis) in an in vitro test. Wherein most of compounds containing benzyl and phenyl in the structure have EC on bacterial leaf blight bacteria and citrus canker bacteria of rice 50 Within 20, especially the compound 28 has excellent activity on rice bacterial leaf blight bacteria and citrus canker bacteria, and EC 50 3.57 and 1.70 μg/mL, respectively; therefore, the compound has great research prospect and can be used for preparing pesticides against plant pathogenic bacteria.
Pharmacological example 2:
EC 50 (median effective concentration) is an important index for evaluating the sensitivity of plant pathogenic bacteria to a compound, and is also an important parameter for setting the concentration of the compound when researching the action mechanism of the target compound. In the concentration gradient experiment, proper 5 concentrations are set by adopting a double dilution method, and finally the inhibition rate of the medicament to plant pathogenic bacteria and the medicament concentration are converted into logarithmic values, and the virulence curve is obtained by SPSS software regression analysis, so that EC is calculated 50 。
Test of the effective Medium concentration EC of the target Compounds against plant pathogens Using the hyphal growth Rate method 50 The test subjects were Botrytis cinerea (B.d), pepper fusarium wilt (F.o) and Rhizoctonia solani (R.s). Placing the Botrytis cinerea (the Botrytis cinerea is in a PDA solid culture medium) into the PDA culture medium, and culturing in a 28 ℃ incubator for 48 hours for later use; placing pepper fusarium wilt bacteria (in a PDA solid culture medium) into a PDA culture medium, and culturing in a 28 ℃ incubator for 48 hours for later use; rhizoctonia solani (in PDA solid)Culture medium) is placed in PDA culture medium, and is cultivated in a culture box at 28 ℃ for 48 hours for standby; the pharmaceutical agent (compound) was prepared as a pharmaceutical agent dilution of different concentrations (e.g., 50, 25, 12.5,6.25,3.125. Mu.g/mL), and PDA drug-containing plates were prepared at a ratio of 9:1 with the pharmaceutical agent dilutions of different concentrations, and the treatment without adding the pharmaceutical agent was used as a control. Preparing bacterial cake at the edge of the activated colony by using a puncher with the inner diameter of 5mm, inoculating a loop to the center of the PDA culture medium of each medicament concentration and control, placing the bacterial cake in a constant temperature incubator for 2-3 d, and measuring the diameter of each colony by using a crisscross method when the control colony grows up to the whole culture dish. The inhibition of each agent was calculated for the different fungi.
Hypha growth inhibition ratio = [ (control colony diameter-agent-treated colony diameter)/control colony diameter-5 ] ×100
The present application is described with the aid of examples, but the contents of examples are not limited thereto, and the experimental results of the target compounds are shown in table 5.
TABLE 5 inhibitory Activity of the Compounds of the application against phytopathogenic fungi
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As can be seen from Table 5, the target compounds were inferior in the in vitro test in the inhibition activity against plant pathogenic fungi (Botrytis cinerea, rhizoctonia solani and Rhizoctonia solani). Wherein, the inhibitory activity of the compounds 11 and 46 on the Botrytis cinerea at the concentration of 50 mug/mL is 78.50% and 83.95%, respectively; the inhibitory activities of compounds 13 and 18 on Rhizoctonia solani at 50 μg/mL were 72.99% and 70.08%, respectively; can be used for preparing pesticides against plant pathogenic fungi.

Claims (9)

1. A class of compounds containing substituted phenyl isopropanolamine or stereoisomers thereof, or salts or solvates thereof, is characterized in that: the compound has a structure shown in a general formula (I):
wherein R is 1 、R 2 And R is 3 Each independently selected from hydrogen, halogen or alkyl; r is R 4 、R 5 One of which may optionally be absent or each independently selected from one or more of hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkenyl, optionally substituted or unsubstituted alkynyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl;
or R is 4 、R 5 Bonding to form an alicyclic, aromatic or heteroaromatic ring;
n＝1、2、3。
2. the substituted phenyl-containing isopropanolamine compound or its stereoisomers, or its salts or its solvates according to claim 1, wherein:
R 1 、R 2 and R is 3 Each independently selected from hydrogen, F, cl, br, methyl;
R 4 、R 5 one of which may optionally be absent, or
Each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, phenyl, benzyl, adamantyl,
n＝1、2、3。
3. The substituted phenyl isopropanolamine-containing compound or its stereoisomers, or its salts or its solvates according to claim 1, characterized by being selected from the following compounds:
4. an intermediate compound for preparing the substituted phenyl isopropanolamine compound or its stereoisomers, or salts or solvates thereof according to claim 1, which is characterized by the following formula:
5. a process for the preparation of a substituted phenyl isopropanolamine-containing compound or its stereoisomers, or a salt thereof or a solvate thereof, according to any of claims 1 to 3, comprising the steps of:
preferably, the method further comprises the steps of:
wherein R is 1 、R 2 、R 3 、R 4 、R 5 The method of claim 1.
6. A composition comprising a compound according to any one of claims 1 to 3 or a stereoisomer thereof, or a salt thereof or a solvate thereof, and an agriculturally acceptable adjuvant or fungicide, insecticide or herbicide; preferably, the formulation of the composition is selected from the group consisting of Emulsifiable Concentrates (EC), powders (DP), wettable Powders (WP), granules (GR), aqueous Solutions (AS), suspensions (SC), ultra low volume sprays (ULV), soluble Powders (SP), microcapsules (MC), smoke agents (FU), aqueous Emulsions (EW), water dispersible granules (WG).
7. Use of a compound according to any one of claims 1 to 3, or a stereoisomer thereof, or a salt thereof, or a solvate thereof, or a composition according to claim 6, for controlling an agricultural pest, preferably a plant bacterial or fungal disease; more preferably, the agricultural pest is a plant leaf blight and a plant canker; most preferably, the agricultural pest is rice bacterial leaf blight, cucumber bacterial leaf blight, konjak bacterial leaf blight, citrus canker, kiwi fruit canker, grape canker, tomato canker, apple canker, cucumber gray mold pathogen, pepper fusarium wilt pathogen, rape sclerotinia rot, wheat red mold pathogen, potato late blight pathogen.
8. A method for controlling agricultural plant diseases and insect pests, which is characterized by comprising the following steps: allowing a compound according to any one of claims 1 to 3 or a stereoisomer thereof, or a salt thereof or a solvate thereof, or a composition according to claim 6 to act on a pest or a living environment thereof; preferably, the pest is a plant bacterial or fungal disease; more preferably, the pest is rice bacterial leaf blight, tobacco bacterial wilt, cucumber bacterial leaf blight, konjak bacterial leaf blight, citrus canker, kiwi fruit canker, grape canker, tomato canker, apple canker, cucumber gray mold, pepper fusarium wilt pathogen, rape sclerotinia rot, wheat red mold pathogen, potato late blight pathogen.
9. A method for protecting plants from agricultural pests comprising the method step wherein the plants are contacted with a compound according to any one of claims 1 to 3 or a stereoisomer thereof, or a salt thereof or a solvate thereof, or a composition according to claim 6.
CN202310702493.2A 2023-06-14 2023-06-14 Substituted phenyl isopropanolamine-containing compound, and preparation method and application thereof Pending CN116730852A (en)

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