Isopropanolamine pyridine ether compound as well as preparation method and application thereof

Abstract

The invention relates to an isopropanolamine pyridine ether compound as well as a preparation method and application thereof. The compound has a structure as shown in a general formula (I): # imgabs0 #. According to the invention, 2, 3-dichloropyridine and hydroquinone are taken as leader, and a series of isopropanolamine pyridine ether compounds are synthesized through three steps; the compound has a good inhibition effect on plant pathogenic bacteria such as Xanthomonas oryzae pv. Oryzae, Xanthomonas oryzae pv. Oryzae, Xanthomonas citri pv. Citri, Xanthomonas syringae pv. Kiwifruit and the like.

Description

Technical Field

[0001] The present invention relates to the technical field of medicinal chemistry, in particular to an isopropylamine-containing pyridine ether compound and a preparation method and application thereof. Background Art

[0002] Rice bacterial leaf blight (BLB) and rice bacterial leaf streak (BLS), caused by Xanthomonas oryzae pv.oryzae (Xoo) and Xanthomonas oryzae pv.oryzicola (Xoc), respectively, are currently the two most serious bacterial diseases threatening rice production, often causing yield losses of 20% to 50%, and there is still a lack of effective control measures. Currently, the prevention and control of bacterial diseases of rice still mainly rely on traditional chemical antimicrobial agents. Similarly, citrus canker (caused by Xanthomonas axonopodis pv.citri) is a disease that is widely distributed worldwide and extremely difficult to control. It causes necrotic lesions and even rot in citrus fruits, seriously affecting yield and marketability. These plant bacterial diseases caused by Xanthomonas not only spread rapidly and cause great harm, but also easily develop drug resistance in a short period of time, becoming a difficult problem for agricultural prevention and control. Currently, the commercially available fungicides for controlling these diseases are limited, relying primarily on traditional agents such as thiophanate-methyl (TC) and chlorothalonil (BT). However, excessive and frequent use of these chemical pesticides not only leads to the rapid development of pathogen resistance but also leaves harmful residues in the environment and agricultural products. Therefore, the development of new, highly effective, low-toxic, and environmentally friendly plant fungicides has become a key area of pesticide development, crucial for ensuring safe crop production and the ecological environment.

[0003] Isopropanolaminopyridinium ether compounds exhibit diverse chemical properties due to their unique structural features. These compounds typically contain a pyridine ring, an ether bond, and an isopropanolamine group with a polar hydroxyl group. The pyridine ring, as an aromatic heterocycle, possesses excellent electron-accepting and coordinating abilities, imparting a degree of rigidity and structural stability to the molecule. The introduction of the ether bond enhances the molecule's hydrophobicity and membrane permeability. The isopropanolamine group imparts strong polarity and good water solubility to the molecule as a whole, while also possessing the ability to form hydrogen bonds, thereby enhancing its interaction with biological targets. These structural advantages have made isopropanolaminopyridinium ether compounds valuable for research in fields such as medicinal chemistry and pesticide chemistry. Studies have shown that these compounds have the potential to inhibit the activity of certain pathogen-related enzymes and regulate cell signaling pathways. Some structural analogs exhibit antibacterial, anti-inflammatory, or antiviral activities. In the field of agricultural chemistry, isopropylaminopyridinium ether compounds are also regarded as a good basis for developing new pesticide candidate molecules due to their flexible synthesis, stable properties and low toxicity. They are expected to be used to improve crop disease resistance or interfere with the nervous system of pests, thereby achieving green and efficient plant protection effects.

[0004] The research progress on the biological activity of isopropylaminopyridinium ether compounds is as follows:

[0005] In 2022, Zhao Lixia et al. [Zhao L, Peng J, Liu F, et al. Discovery of novel phenoxypyridine as promising protoporphyrinogen IX oxidase inhibitors [J]. Pesticide Biochemistry and Physiology, 2022, 184: 105102.] started from the active fragments of several known commercially available herbicides and designed and synthesized a series of protoporphyrinogen oxidase inhibitors (PPO inhibitors) with diphenyl ether scaffolds through substructure splicing and bioisosteric methods. The test results showed that the newly synthesized target product had excellent PPO inhibitory activity, with an IC50 value of 0.032 mg / L to 3.245 mg / L for corn PPO. Among all the target compounds, compound 1-12a exhibited the best herbicidal activity, with an IC 50 The value is 0.032mg / L.

[0006] In 2022, Wang Lizeng et al. [Wang L, Yang Z, Pan S, et al. A new potential aphicide against Myzus persicae: Design, synthesis and 3D-QSAR of novel phenoxypyridine derivatives containing 4-aminopyrimidine [J]. Journal of Molecular Structure, 2022, 1262: 132949.] designed and synthesized 31 phenoxypyridine derivatives containing 4-aminopyrimidine using the intermediate derivatization method (IDM). The bioassay results showed that some compounds exhibited significant insecticidal activity against peach aphids (M persicae) in vivo. In particular, the activity of 1-11a (LC 50 : 0.34 mg / L) is higher than pymetrozine, anthracene and other derivatives.

[0007] In 2021, Zhao Lixia et al. [Zhao LX, Wang ZX, Peng JF, et al. Design, synthesis, andherbicidal activity of novel phenoxypyridine derivatives containing natural product coumarin [J]. Pest Management Science, 2021, 77 (10): 4785-4798.] synthesized compounds with good herbicidal activity by connecting the bioisotope structure of diphenyl ether pyridine with substituted coumarin. The bioassay results showed that compound 1-9a exhibited good herbicidal activity in greenhouse and field tests, and its IC 50 The selectivity and safety of cotton and soybean are better than the commercial herbicide oxyfluorfen (LC 50 :0.07368mg / L).

[0008] In 2020, Ran Fangsheng et al. [Ran F, Liu Y, Yu S, et al. Design and synthesis of novel 1-substituted 3-(6-phenoxypyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineanalogs as selective BTK inhibitors for the treatment of mantle cell lymphoma[J]. Bioorganic Chemistry, 2020, 94: 103367.] studied and synthesized a series of novel 3-(6-phenoxypyridin-3-yl)-4-amine-1H-pyrazolo[3,4-d]pyrimidine derivatives that can effectively inhibit Bruton's tyrosine kinase (BTK). Among them, compound 1-8a explained the effective BTK inhibitory activity and could completely inhibit the phosphorylation of BTK and PLCγ2 in Z138 cells at low micromolar concentrations. Compared with IBN (the first BTK inhibitor), compounds 1-8a showed 3-40-fold enhanced antiproliferative activity in MCL cell lines, with IC 50 The values were lower than 1 μM. Low molar doses of 1-8a could induce strong apoptosis in Jeko-1 and Z138 cells. Summary of the Invention

[0009] One of the purposes of the present invention is to provide an isopropylamine-containing pyridine ether compound or its stereoisomer, or its salt or solvate.

[0010] Another object of the present invention is to provide an intermediate compound for preparing the above-mentioned compound or its stereoisomer, or its salt or solvate and a preparation method thereof.

[0011] Another object of the present invention is to provide a composition containing the above compound or its stereoisomer, or its salt or solvate.

[0012] Another object of the present invention is to provide the use of the above compound or its stereoisomer, or its salt or solvate, or the composition.

[0013] Another object of the present invention is to provide a method for controlling agricultural pests and diseases using the above-mentioned compound or its stereoisomer, or its salt or solvate, or the composition.

[0014] To achieve the above object, the present invention adopts the following technical solutions:

[0015] An isopropylamino-containing pyridine ether compound or its stereoisomer, or its salt or solvate, wherein the compound has a structure as shown in the general formula (I):

[0016]

[0017] where R

[0018] One or more selected from hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted aryl, and optionally substituted or unsubstituted heteroaryl;

[0019] The present invention also provides an intermediate compound for preparing the isopropanolamino-containing pyridine ether compound or its stereoisomer, or its salt or solvate:

[0020]

[0021] The present invention also provides a method for preparing the aforementioned isopropylamine-containing pyridine ether compound or its stereoisomer, or its salt or solvate, comprising the following steps:

[0022]

[0023] wherein R is selected from one or more of hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted aryl, and optionally substituted or unsubstituted heteroaryl;

[0024] The term "alkyl" as used herein includes both branched and straight chain saturated hydrocarbon groups having the specified number of carbon atoms. For example, "C 1-10 Alkyl (or alkylene) is C1, C2, C3, C4, C5, C6, C7, C8, C9 and C 10 Alkyl. In addition, for example, "C 1-6 "Alkyl" means an alkyl group having 1 to 6 carbon atoms. The alkyl group may be unsubstituted or substituted such that one or more of its hydrogen atoms are replaced by other chemical groups. Examples of alkyl groups include, but are not limited to, methyl (Me), ethyl (Et), propyl (such as n-propyl and isopropyl), butyl (such as n-butyl, isobutyl, tert-butyl), pentyl (such as n-pentyl, isopentyl, neopentyl), and the like.

[0025] As used herein, the term "substituted" refers to the replacement of any one or more hydrogen atoms on a designated atom or group with a selected designated group, provided that the general valence of the designated atom is not exceeded. Unless otherwise specified, the substituents are named to the central structure. For example, it is understood that when (cycloalkyl)alkyl is a possible substituent, the point of attachment of the substituent to the central structure is in the alkyl portion. A ring double bond as used herein is a double bond formed between two adjacent ring atoms (e.g., C=C, C=N, or N=N). When referring to substitution, particularly polysubstitution, it is meant that multiple substituents are substituted at various positions on the designated group, e.g., dichlorophenyl refers to 1,2-dichlorophenyl, 1,3-dichlorophenyl, and 1,4-dichlorophenyl.

[0026] Combinations of substituents and variables are permissible only if such combinations result in stable compounds or useful synthetic intermediates.A stable compound or stable structure implies that the compound is sufficiently stable when isolated to a useful degree of purity from a reaction mixture, and then formulated into an efficacious therapeutic agent.

[0027] The term "aryl" refers to a monocyclic or bicyclic aromatic hydrocarbon group having 6 to 12 carbon atoms in the ring portion, such as phenyl and naphthyl, each of which may be substituted.

[0028] 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, preferably one, two, or three heteroatoms selected from O, S, and N. Each ring of a heteroaryl group containing a heteroatom may contain one or two oxygen or sulfur atoms and / or from one to four nitrogen atoms, provided that the total number of heteroatoms in each ring is four or fewer and each ring has at least one carbon atom. The fused rings completing the bicyclic and tricyclic groups may contain only carbon atoms and may be saturated, partially saturated, or unsaturated. The nitrogen and sulfur atoms may optionally be oxidized, and the nitrogen atoms may optionally be quaternized. Bicyclic or tricyclic heteroaryl groups must include at least one fully aromatic ring; the nitrogen and other fused rings may be aromatic or non-aromatic. The heteroaryl group may be attached at any available nitrogen or carbon atom in any ring. When valence permits, if the other ring is a cycloalkyl or heterocycle, it is additionally optionally substituted with =0 (oxygen).

[0029] Exemplary monocyclic heteroaryl groups include pyrazolyl, imidazolyl, furanyl, thienyl, pyridinyl, pyrimidinyl, and the like.

[0030] If not otherwise indicated, the compounds of the present invention are understood to include both the free form and the salts thereof. The term "salt" refers to acidic and / or basic salts formed with inorganic and / or organic acids and bases. In addition, the term "salt" may include zwitterions (inner salts), such as when the compound of Formula I contains a basic moiety such as an amine. Pharmaceutically acceptable (i.e., non-toxic, physiologically acceptable) salts are preferred, such as acceptable metal and amine salts, in which the cation does not significantly contribute to the toxicity or biological activity of the salt. However, other salts may be useful, such as when separation or purification steps are employed during preparation, and are therefore also included within the scope of the present invention.

[0031] When a substituent is referred to as an alkylaryl group or a heteroarylamino group, or when these substituents are specifically a specific alkylaryl group or heteroarylamino group, it refers to one to three of the above substituents. For example, methylphenyl refers to a phenyl group substituted with one to three methyl groups.

[0032] By adopting the above technical solution, the present invention synthesizes a series of isopropanolamino-containing pyridine ether compounds based on 2,3-dichloropyridine and hydroquinone, and finds that the compounds have a good inhibitory effect on pathogenic bacteria, especially pathogens such as citrus canker (Xanthomonas axonopodis pv. citri), rice bacterial blight (Xanthomonas oryzae pv. oryzae), rice streak pathogen (Xanthomonas oryzae pv. oryzicola), and kiwifruit canker (Pseudomonas syringae pv. actinidiae). These compounds all have a good inhibitory effect, providing an important scientific basis for the research and development and creation of new pesticides. Example

[0033] The present invention will be further described below by way of examples. It should be understood that the methods described in the examples of the present invention are only intended to illustrate the present invention, rather than to limit the present invention.

[0034] All the raw materials and solvents used in the examples are commercially available products of corresponding purity.

[0035] Example 1: Preparation of intermediate 4-((3-chloropyridin-2-yl)oxy)phenol

[0036] 2,3-Dichloropyridine (6.8 mmol), hydroquinone (8.1 mmol), and potassium carbonate (K2CO3, 16.2 mmol) were added to a 15 mL reaction flask. 10 mL of DMSO was added as solvent and the reaction was heated at 100°C for 5 h. After the reaction, the reaction solution was cooled to ice bath temperature, the pH was adjusted to neutral (pH = 7), and the solution was allowed to stand to precipitate a solid. The resulting precipitate was filtered and dried to obtain a white solid with a yield of 58.43%.

[0037] Example 2: Preparation of intermediate 3-chloro-2-(4-(epoxy-2-ylmethoxy)phenoxy)pyridine

[0038] 4-((3-chloropyridin-2-yl)oxy)phenol (2.26 mmol), epibromohydrin (2.93 mmol), and potassium hydroxide (KOH, 2.71 mmol) were added to a 25 mL round-bottom flask. 8 mL of N,N-dimethylformamide (DMF) was added as the solvent and the reaction was stirred at room temperature for 8 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The resulting organic phase was washed with saturated ammonium chloride solution, dried to remove the solvent, and purified by column chromatography (P / E = 20:1 → 10:1) to obtain a white solid in a 41.2% yield.

[0039] Example 3: Preparation of 1-[4-((3-chloropyridin-2-yl)oxy)phenoxy]-3-(dipropylamino)propan-2-ol (PyE9)

[0040] 3-Chloro-2-(4-(epoxy-2-ylmethoxy)phenoxy)pyridine (1.08 mmol), propylenediamine (3.24 mmol), K2CO3 (0.54 mmol), and isopropyl alcohol (IPA, 8 mL) were added to a 15 mL pressure tube and heated at 60°C for 36 h. After completion of the reaction, the mixture was extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure at 40°C. The crude product was purified by column chromatography (DCM / M = 100:1 → 50:1) to obtain a white solid in a yield of 76.8%.

[0041] Example 4: Preparation of the target compound 1-[4-((3-chloropyridin-2-yl)oxy)phenoxy]-3-(4-phenylpiperazin-1-yl)propan-2-ol (PyE24)

[0042] 3-Chloro-2-(4-(epoxy-2-ylmethoxy)phenoxy)pyridine (1.08 mmol), N-phenylpiperazine (3.24 mmol), KCO (0.54 mmol), and isopropyl alcohol (IPA, 8 mL) were added to a 15 mL pressure tube and heated at 60°C for 36 h. After completion of the reaction, the mixture was extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure at 40°C. The crude product was purified by column chromatography (DCM / M = 100:1 → 10:1) to obtain a yellow solid in a 57.4% yield.

[0043] Example 5: Preparation of the target compound 1-[4-((3-chloropyridin-2-yl)oxy)phenoxy]-3-(4-(pyrimidin-2-yl)piperazin-1-yl)propan-2-ol (PyE25)

[0044] 3-Chloro-2-(4-(epoxy-2-ylmethoxy)phenoxy)pyridine (1.08 mmol), 1-(pyrimidin-2-yl)piperazine (3.24 mmol), KCO (0.54 mmol), and isopropyl alcohol (IPA, 8 mL) were added to a 15 mL pressure tube and heated at 60°C for 36 h. After completion of the reaction, the mixture was extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure at 40°C. The crude product was purified by column chromatography (DCM / M = 100:1 → 10:1) to obtain a yellow solid in a 77.7% yield.

[0045] Example 6: Preparation of the target compound 1-[(4-chlorobenzyl)amino]-3-[4-((3-chloropyridin-2-yl)oxy)phenoxy]propan-2-ol (PyE28)

[0046] 3-Chloro-2-(4-(epoxy-2-ylmethoxy)phenoxy)pyridine (1.08 mmol), N-methyl-4-chlorobenzylamine (3.24 mmol), K2CO3 (0.54 mmol), and isopropyl alcohol (IPA, 8 mL) were added to a 15 mL pressure tube and heated at 60°C for 36 h. After completion of the reaction, the mixture was extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure at 40°C. The crude product was purified by column chromatography (DCM / M = 100:1 → 50:1) to obtain a yellow solid in a 48.6% yield.

[0047] Other compounds were prepared by similar methods to the above examples, replacing corresponding starting materials.

[0048] The structures, H NMR spectra, and C NMR spectra of the synthesized pyrazole amide compounds are shown in Table 1 , and their physicochemical properties are shown in Table 2 .

[0049] Table 1 H NMR and C NMR data of the compounds

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] Table 2 Physicochemical properties of target compounds

[0058]

[0059]

[0060] Pharmacological Example 1:

[0061] Turbidimetric testing was used to determine the inhibitory effects of target compounds on plant pathogens Xanthophyllum citri (Xac), Xanthophyllum oryzae (Xoo), Xanthophyllum oryzae (Xoc), and Xanthophyllum kiwifruit (Psa). DMSO dissolved in the culture medium served as a blank control. Xanthophyllum citri (Xac), Xanthophyllum oryzae (Xoo), Xanthophyllum oryzae (Xoc), and Xanthophyllum kiwifruit (Psa) were cultured in NB medium and shaken at 28°C and 180 rpm in a constant temperature shaker until the logarithmic growth phase. Xanthophyllum citri (Xac), Xanthophyllum oryzae (Xoo), Xanthophyllum oryzae (Xoc), and Xanthophyllum kiwifruit (Psa) were cultured on NA solid medium and then incubated in NB medium and shaken at 28°C and 180 rpm in a constant temperature shaker until the logarithmic growth phase. 5 mL of NB liquid (523 medium) containing different concentrations of the drug (compound) (e.g., 50, 25, 12.5 μg / mL) was added to a test tube, and 40 μL of NB liquid medium (523 medium) containing plant pathogenic bacteria was added. The mixture was shaken in a constant temperature shaker at 28°C and 180 rpm for 48 hours. The OD of the bacterial solution at each concentration was measured on a spectrophotometer. 595 The OD of the corresponding concentration of toxic sterile NB liquid culture medium was also measured. 595 value.

[0062] EC 50Median effective concentration (MEC) is an important indicator for evaluating the sensitivity of plant pathogens to compounds. It is also an important parameter for setting compound concentration when studying the mechanism of action of target compounds. In the concentration gradient experiment, the two-fold dilution method was used to set 5 appropriate concentrations. Finally, the inhibition rate of the agent on plant pathogens and the agent concentration were converted into logarithmic values. The toxicity curve was obtained through regression analysis using SPSS software, and the EC was calculated. 50 .

[0063] The effective medium concentration EC of target compounds against plant pathogens was tested by turbidimetric method. 50 The test subjects were Xanthophyllotoxin (Xac), Xanthophyllotoxin (Xoo), Xanthophyllotoxin (Xoc), and Xanthophyllotoxin (Psa). DMSO was dissolved in the culture medium as a blank control. Xanthophyllotoxin (Xac) was placed in NB medium (Xac) and cultured in a constant temperature shaker at 28°C and 180 rpm until the logarithmic growth phase. Xanthophyllotoxin (Xac), Xanthophyllotoxin (Xoc), and Xanthophyllotoxin (Psa) were transferred from 523 solid culture medium to 523 medium. The solid culture medium was then placed in NB medium and cultured in a constant temperature shaker at 28°C and 180 rpm until the logarithmic growth phase. 5 mL of NB liquid medium containing different concentrations of the drug (compound) (e.g., 50, 25, 12.5, 6.25, 3.125 μg / mL) was added to the test tube, and 40 μL of NB liquid medium containing plant pathogenic bacteria (523 medium) was added to each test tube. The culture was shaken in a constant temperature shaker at 28°C and 180 rpm for 48 hours. The OD value of the bacterial solution at each concentration was measured on a spectrophotometer. 595 The OD of the corresponding concentration of toxic sterile NB liquid culture medium was also measured. 595 value.

[0064] Corrected OD value = OD value of bacterial culture medium - OD value of sterile culture medium

[0065] Inhibition rate % = [(corrected OD value of control culture medium bacteria liquid - corrected OD value of poisonous culture medium) / corrected OD value of control culture medium bacteria liquid] × 100

[0066] The examples of the present invention are used to illustrate the technical solutions of the present invention, but the contents of the examples are not limited thereto. The experimental results of the target compounds are shown in Table 3.

[0067] Table 3 EC values of novel pyrazole amide compounds against plant pathogenic fungi 50

[0068]

[0069]

[0070] As can be seen from Table 3, in the in vitro test, the target compounds showed good inhibitory activity against plant pathogenic bacteria (such as Xanthomonas citri, Xanthomonas oryzae and Xanthomonas oryzae). Among them, compounds 10, 26, 27 and 28 showed good inhibitory activity against Xanthomonas citri, with their EC 50 3.70, 3.85, 3.24, and 2.91 μg / mL, respectively; compounds 1, 23, 26, 27, 28, and 36 also showed good inhibitory activity against bacterial blight of rice, and their EC 50 and 3.33, 4.72, 2.81, 2.17, 2.03, and 2.80 μg / mL, respectively. Meanwhile, compound 2 also showed good inhibitory activity against rice streak pathogen, and its EC 50 The concentration of 4.47 μg / mL can be used to prepare pesticides against plant pathogenic bacteria.

Claims

1. An isopropylamine-containing pyridine ether compound or a stereoisomer thereof, or a salt thereof or a solvate thereof, characterized in that: The compound has a structure as shown in general formula (I): Wherein R is selected from hydrogen, alkyl, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted amide, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl, and optionally substituted or unsubstituted nitrogen-containing group.

2. The isopropylamino pyridine ether compound according to claim 1, or a stereoisomer thereof, or a salt thereof, or a solvate thereof, wherein: R is selected from hydrogen, methyl, ethyl, cyano, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, formyl, acetyl, pyridyl, pyrrolyl, amino, piperidyl, piperazinyl, morpholinyl, 3. The isopropylamine-containing pyridine ether compound according to claim 1, or its stereoisomer, or its salt or solvate, is characterized in that Selected from the following compounds:

4. An intermediate compound for preparing the isopropylamine-containing pyridine ether compound or its stereoisomer, or its salt or solvate according to claim 1, characterized in that As shown below:

5. The method for preparing an isopropylamine-containing pyridine ether compound or a stereoisomer thereof, or a salt thereof or a solvate thereof according to any one of claims 1 to 3, characterized in that The steps include: Further including: Preferred include: Most preferably include: where R is as described above.

6. A composition characterized in that Contains the compound according to any one of claims 1 to 3 or its stereoisomer, or its salt or solvate, and an agriculturally usable adjuvant or fungicide, insecticide or herbicide; preferably, the composition is in the form of an emulsifiable concentrate (EC), a dust (DP), a wettable powder (WP), a granule (GR), an aqueous solution (AS), a suspension (SC), an ultra-low volume spray (ULV), a soluble powder (SP), a microcapsule (MC), a smoke agent (FU), an emulsion in water (EW), and a water-dispersible granule (WG).

7. Use of the compound or stereoisomer thereof, or salt or solvate thereof according to any one of claims 1 to 3, or the composition according to claim 6 for preventing and controlling agricultural pests and diseases, preferably, the agricultural pests and diseases are bacterial diseases of plants; more preferably, the agricultural pests and diseases are plant leaf blight and plant canker; most preferably, the agricultural pests and diseases are rice bacterial leaf blight, cucumber bacterial leaf blight, konjac bacterial leaf blight, citrus canker, kiwifruit canker, mango angular leaf spot, grape canker, tomato canker, apple canker, cucumber gray mold, pepper wilt, rapeseed sclerotinia, wheat fusarium head blight, potato late blight, rice leaf streak, and rice fine streak.

8. A method for preventing and controlling agricultural pests and diseases, characterized by: The compound according to any one of claims 1 to 3 or its stereoisomer, or its salt or solvate, or the composition according to claim 6 is allowed to act on a pest or its living environment; preferably, the pest is a bacterial or fungal plant disease; more preferably, the agricultural pest is rice bacterial blight, cucumber bacterial blight, konjac bacterial blight, citrus canker, kiwi canker, mango angular leaf spot, grape canker, tomato canker, apple canker, cucumber gray mold, pepper wilt pathogen, rapeseed sclerotinia, wheat fusarium wilt, potato late blight, rice leaf streak pathogen, and rice fine stripe disease.

9. A method for protecting plants from agricultural pests and diseases, comprising the step of contacting the plant with the compound or stereoisomer thereof, or a salt or solvate thereof according to any one of claims 1 to 3, or the composition according to claim 6.

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