4-(4-hydroxyphenoxy) benzoate derivative as well as preparation method and application thereof

Abstract

The invention belongs to the field of pesticide bactericides, and discloses a pesticide containing 4-(4-hydroxyphenoxy) benzoate derivatives and application of the 4-(4-hydroxyphenoxy) benzoate derivatives, and the 4-(4-hydroxyphenoxy) benzoate derivatives have a structure as shown in a formula (I).

Description

TECHNICAL FIELD

[0001] The present application relates to the field of fungicides, in particular to 4-(4-hydroxyphenoxy)benzoate derivatives, their preparation method and application. BACKGROUND

[0002] Fungal diseases continuously threaten global food production, causing severe yield and quality losses. Due to the concealment of the infection process, the fast adaptation of pathogens, and the complex interactions among crops, environment, and pathogens, it is a great challenge to implement effective prevention and control at the key infection stage. The successful infection of fungal pathogens depends on their ability to perceive and adapt to the dynamic nutritional environment in the host. Among the essential nutrients, nitrogen plays a core role in fungal growth, development, and pathogenicity. Existing studies have shown that fungal pathogens encounter nitrogen stress during the infection process and have evolved precise mechanisms to re-regulate nitrogen acquisition and utilization to overcome this nutritional starvation pressure. Therefore, targeting the nitrogen response regulatory network provides a new approach for developing broad-spectrum antifungal strategies.

[0003] As a core hub, the target of rapamycin (TOR) kinase coordinates cell growth, metabolism, and stress response by integrating nutritional signals. The TOR signaling pathway is a conserved regulator of nutrient perception and cell growth in eukaryotes. In the present application, it is found that the lysine acetylation modification of the Sap protein (FgSap) of Fusarium graminearum is a key molecular switch that regulates its interaction with Sit4, thereby affecting nitrogen utilization, toxin synthesis, and autophagy processes. Based on the structural characteristics of FgSap, we have developed small molecule compounds that can specifically bind to Sap and block its acetylation modification, thereby effectively inhibiting the TOR signaling pathway and developing a highly efficient and broad-spectrum fungicide with a novel mechanism of action. SUMMARY

[0004] The purpose of the present application is to provide a new type of 4-(4-hydroxyphenoxy)benzoate derivative preparation and application. The compounds of the present application have high fungicidal activity against plant pathogenic fungi.

[0005] To achieve the above purpose, the first aspect of the present application provides a 4-(4-hydroxyphenoxy)benzoate derivative compound having the structure shown in formula I, Formula (I)

[0006] wherein,

[0007] A is C1-C 12 alkyl and / or C1-C 12 alkoxy substitution and / or halogen and / or N-substituted or unsubstituted five- or six-membered heterocycle, benzene ring or C3-C8 cycloalkyl;

[0008] X is in any substitution position in A, and is an amide group or an amino group that is O, S, N-substituted or unsubstituted;

[0009] B represents sulfonyl, sulfinyl, carbonyl, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 alkylamine, halogen-substituted C1-C12 alkyl, and S-substituted alkyl.

[0010] Q represents H, halogen, hydroxyl, amino, cyano, nitro, phenyl, pyridyl, C1-C. 12 Alkyl groups, halogen-substituted C1-C 12 Alkyl, C1-C 12 Alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C1-C substituted with halogen and / or N-substituted 12 Alkoxy groups, composed of C1-C 12 Alkyl and / or C1-C 12 Alkoxy-substituted and / or halogenated and / or N-substituted or unsubstituted phenyl, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazole, C1-C 12 Alkyl and / or C1-C 12 Alkoxy-substituted and / or halogenated and / or N-substituted or unsubstituted C3-C8 heterocycles;

[0011] The terminology of this invention will be explained below.

[0012] “C1-C 12 "alkyl" refers to an alkyl group with a total number of carbon atoms of 1-12, including straight-chain alkyl, branched alkyl, or cycloalkyl. For example, it can be a straight-chain alkyl, branched alkyl, or cycloalkyl group with a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, cyclopropyl, methylcyclopropyl, ethylcyclopropyl, cyclobutyl, methylcyclobutyl, ethylcyclobutyl, cyclopentyl, methylcyclopentyl, ethylcyclopentyl, cyclohexyl, methylcyclohexyl, ethylcyclohexyl, etc.

[0013] In this invention, "C1-C" 12 "alkoxy group" refers to an alkoxy group with 1-12 carbon atoms, such as methyloxy, ethyloxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, tert-butyloxy, n-pentyloxy, isopentyloxy, n-hexyloxy, cyclopropyloxy, methylcyclopropyloxy, ethylcyclopropyloxy, cyclopentyloxy, methylcyclopentyloxy, and cyclohexyloxy.

[0014] In this invention, "C1-C" 12"Alkylamino" indicates an amino group with alkyl substitution having 1-12 carbon atoms, which can be mono- and / or dialkyl-substituted, wherein the alkyl group can be the same and / or different when dialkyl-substituted.

[0015] In this invention, "C2-C6 alkenyl" refers to a monoalkenyl, dienyl, or polyalkenyl group having 1-6 carbon atoms, such as vinyl, n-propenyl, isopropenyl, n-butenyl, n-dibutenyl, isobutenyl, tert-butenyl, n-pentenyl, 1,3-pentadienyl, isopentenyl, n-hexenyl, 1,3-hexadienyl, cyclopropenyl, methylcyclopropenyl, ethylcyclopropenyl, cyclopentenyl, methylcyclopentenyl, and cyclohexenyl.

[0016] In this invention, "C2-C6 alkynyl" refers to a mono-alkynyl, di-alkynyl, or poly-alkynyl group having 1-6 carbon atoms. Examples include ethynyl, n-propynyl, isopropynyl, n-butynyl, n-dibutynyl, isobutynyl, tert-butynyl, n-pentynyl, 1,3-pentadiynyl, isopentenynyl, n-hexynyl, 1,3-hexadiynyl, cyclopropynyl, methylcyclopropynyl, ethylcyclopropynyl, cyclopentynyl, methylcyclopentynyl, and cyclohexynyl.

[0017] In this invention, the term "substituted or unsubstituted C3-C8 heterocycle" refers to a heterocycle containing at least one of N, O, and S.

[0018] In this invention, "halogen" means at least one element selected from fluorine, chlorine, bromine, and iodine.

[0019] The invention does not specifically limit the method for synthesizing the 4-(4-hydroxyphenoxy)benzoate derivatives shown in Formula (I). Those skilled in the art can obtain suitable methods for preparing the derivatives shown in Formula (I) by combining the compound structure provided by the invention with the synthesis methods in the field of chemistry. The invention will not elaborate on these methods here.

[0020] The second aspect of the present invention provides a method for preparing the compound containing the 4-(4-hydroxyphenoxy)benzoate derivative described in the first aspect.

[0021] The following synthetic route was used for its synthesis, wherein the position and type of substituents were changed according to the specific compound being prepared:

[0022]

[0023] Specifically,

[0024] In step a, raw material I and alkali are dissolved in a solvent, p-fluorobenzonitrile is added, and the mixture is stirred at 0℃-110℃. After the reaction is complete, dilute hydrochloric acid is added to quench the reaction, followed by extraction, washing with saturated sodium chloride solution, combining the organic layers, drying and concentrating to obtain intermediate II.

[0025] In step b, intermediate II is dissolved in a solvent, an aqueous solution of alkali is added, and the mixture is stirred at 0℃-90℃. After the reaction is complete, the solvent is evaporated to dryness, and the mixture is extracted with ethyl acetate. The aqueous phase is acidified with concentrated hydrochloric acid and filtered to obtain intermediate III.

[0026] In step c, raw material IV is dissolved in a solvent, alkali is added, and the mixture is stirred at 0℃-90℃. After the reaction is complete, the solvent is evaporated, the mixture is extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers are combined, dried, concentrated, and column chromatography is used to obtain intermediate V.

[0027] In step d, intermediate V is dissolved in a solvent, sodium borohydride is added, and the mixture is stirred at 0℃-90℃. After the reaction is complete, water is added, the solvent is evaporated, the mixture is extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers are combined, dried, concentrated, and column chromatography is used to obtain intermediate VI.

[0028] In step e, intermediate VI is dissolved in a solvent, carbon tetrabromide and triphenylphosphine are added, and the mixture is stirred at room temperature until the reaction is complete. Water is added, the solvent is evaporated to dryness, the mixture is extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers are combined, dried, concentrated, and column chromatography is used to obtain intermediate VII.

[0029] In step f, intermediate III is dissolved in a solvent, alkali is added, and the mixture is stirred at 50-90°C. Intermediate VII is then added, and after the reaction is complete, water is added, the solvent is evaporated to dryness, the mixture is extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers are combined, dried, concentrated, and column chromatography is performed to obtain intermediate VII.

[0030] The solvent in step af is selected from water, N,N-dimethylformamide, acetonitrile, dichloromethane, 1,4-dioxane, toluene, dimethyl sulfoxide, acetic acid, tetrahydrofuran, methanol, and ethanol.

[0031] A third aspect of the invention provides the application of the compound as a pesticide fungicide. This is for the control of plant diseases caused by pathogenic fungi, including at least one of the following: *Alternaria solani* (tomato early blight); *Botrytis cinerea* (tomato gray mold); *Cercospora arachidicola* (peanut brown spot); *Fusarium graminearum* (wheat scab); *Phytophthora infestans* (potato late blight); *Physalospora piricola* (apple ring rot); *Rhizoctonia solani* (rice sheath blight); *Sclerotinia sclerotiorum* (rapeseed sclerotinia sclerotiorum); and rice blast.

[0032] Preferably, in this invention, the pathogenic fungus includes at least one of the following: Botrytis cinerea (tomato gray mold); Fusarium graminearum (wheat scab); Rhizoctonia solani (rice sheath blight); Sclerotinia sclerotiorum (rapeseed sclerotinia sclerotiorum); and rice blast.

[0033] A fourth aspect of the present invention provides a pesticide fungicide composed of an active ingredient and excipients, wherein the active ingredient includes at least one of the compounds described in the first aspect above.

[0034] This invention has the following advantages: First, the compounds of this invention exhibit novel modes of action in terms of fungicide activity. They contain 4-(4-hydroxyphenoxy)benzoate derivatives that act on Sap acetylation; no related compounds have been reported to act on this target, and there are no commercially available fungicides. In particular, the compounds of this invention possess high fungicidal activity and strong inhibitory effects against plant pathogenic fungi, demonstrating excellent application value. Second, the compounds of this invention have simple structures and are easy to prepare. Attached Figure Description

[0035] Figure 1 Compound ag (NJU173) can effectively prevent and control wheat scab and reduce DON toxin while exhibiting broad-spectrum antifungal activity.

[0036] Figure 2 Safety of compound ag (NJU173) in mung bean and tomato plants. Detailed Implementation

[0037] Example 1

[0038] The compound shown in formula VIII-1 was synthesized using the following synthetic route.

[0039]

[0040] Synthesis of intermediate of formula II-1

[0041] Hydroquinone (10 mmol) was dissolved in N,N-dimethylformamide solution, potassium carbonate (15 mmol) was added, and the reaction was carried out at room temperature for half an hour. Then p-fluorobenzonitrile was added. The temperature was raised to 100 °C. The reaction was carried out for 3-4 hours. The reaction progress was monitored by TLC. After the reaction was completed, the solvent was removed. The remaining solid was dissolved in ethyl acetate and washed twice with saturated NaCl. The organic phase was collected, dried over anhydrous Na2SO4, and concentrated to give intermediate II-1.

[0042] Synthesis of intermediate of formula III-1

[0043] Intermediate II-1 (10 mmol) was dissolved in methanol, and an aqueous solution of sodium hydroxide (30 mmol) was added. The mixture was heated to reflux, and the reaction was monitored by TLC. After the reaction was complete, the solvent was evaporated, and the mixture was extracted with ethyl acetate. The aqueous phase was acidified with concentrated hydrochloric acid, and the pH was adjusted to 1-2. The mixture was then filtered to obtain intermediate III-1.

[0044] Synthesis of Formula V-1 intermediate

[0045] p-hydroxybenzaldehyde (10 mmol) was dissolved in tetrahydrofuran solution, and triethylamine (20 mmol) and benzoyl chloride (10 mmol) were added. The mixture was stirred at room temperature, and the reaction was monitored by TLC. After the reaction was completed, ethyl acetate was added, the mixture was filtered, and the filtrate was concentrated by rotary evaporation to obtain intermediate V-1.

[0046] Synthesis of Formula VI-1 intermediate

[0047] Intermediate V-1 (10 mmol) was dissolved in ultra-dry tetrahydrofuran solution, and sodium borohydride (40 mmol) was added at 0 °C. The reaction was heated to room temperature, and the reaction was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, and the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, and the organic layers were combined, dried, concentrated, and column chromatography was used to obtain intermediate VI-1.

[0048] Synthesis of intermediate of formula VII-1

[0049] Intermediate VI-1 (10 mmol) was dissolved in tetrahydrofuran solution, carbon tetrabromide (15 mmol) was added, and triphenylphosphine (20 mmol) was added at 0 °C. The mixture was heated to room temperature and stirred. The reaction was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, and the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, and the organic layers were combined, dried, concentrated, and column chromatography was used to obtain intermediate VII-1.

[0050] Synthesis of intermediate VIII-1

[0051] Intermediate III-1 (2 mmol) was dissolved in N,N-dimethylformamide solution, sodium bicarbonate (3 mmol) was added, and the mixture was stirred at 70 °C for 10 minutes. The mixture was then cooled to 50 °C, and intermediate VII-1 (6 mmol) was added. The reaction was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, and the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, and the organic layers were combined. The mixture was dried and concentrated by column chromatography to obtain intermediate VIII-1.

[0052] Example 2

[0053] The compound shown in formula VIII-2 was synthesized using the following synthetic route.

[0054] .

[0055] Synthesis of intermediate of formula II-1

[0056] Hydroquinone (10 mmol) was dissolved in N,N-dimethylformamide solution, potassium carbonate (15 mmol) was added, and the reaction was carried out at room temperature for half an hour. Then p-fluorobenzonitrile was added. The temperature was raised to 100 °C. The reaction was carried out for 3-4 hours. The reaction progress was monitored by TLC. After the reaction was completed, the solvent was removed. The remaining solid was dissolved in ethyl acetate and washed twice with saturated NaCl. The organic phase was collected, dried over anhydrous Na2SO4, and concentrated to give intermediate II-1.

[0057] Synthesis of intermediate of formula III-1

[0058] Intermediate II-1 (10 mmol) was dissolved in methanol, and an aqueous solution of sodium hydroxide (30 mmol) was added. The mixture was heated to reflux, and the reaction was monitored by TLC. After the reaction was complete, the solvent was evaporated, and the mixture was extracted with ethyl acetate. The aqueous phase was acidified with concentrated hydrochloric acid, and the pH was adjusted to 1-2. The mixture was then filtered to obtain intermediate III-1.

[0059] Synthesis of Formula V-2 intermediate

[0060] p-hydroxybenzaldehyde (10 mmol) was dissolved in tetrahydrofuran solution, and triethylamine (20 mmol) and benzenesulfonyl chloride (10 mmol) were added. The mixture was stirred at room temperature, and the reaction was monitored by TLC. After the reaction was completed, ethyl acetate was added, the mixture was filtered, and the filtrate was concentrated by rotary evaporation to obtain intermediate V-2.

[0061] Synthesis of Formula VI-2 intermediate

[0062] Intermediate V-2 (10 mmol) was dissolved in ultra-dry tetrahydrofuran solution, sodium borohydride (40 mmol) was added at 0 °C, and the reaction was heated to room temperature. The reaction progress was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers were combined, dried and concentrated by column chromatography to obtain intermediate VI-2.

[0063] Synthesis of intermediate of formula VII-2

[0064] Intermediate VI-2 (10 mmol) was dissolved in tetrahydrofuran solution, carbon tetrabromide (15 mmol) was added, and triphenylphosphine (20 mmol) was added at 0 °C. The mixture was heated to room temperature and stirred. The reaction was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers were combined, dried and concentrated, and column chromatography was used to obtain intermediate VII-2.

[0065] Synthesis of intermediate VIII-2

[0066] Intermediate III-1 (2 mmol) was dissolved in N,N-dimethylformamide solution, sodium bicarbonate (3 mmol) was added, and the mixture was stirred at 70 °C for 10 minutes. The mixture was then cooled to 50 °C, and intermediate VII-2 (6 mmol) was added. The reaction was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, and the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, and the organic layers were combined. The mixture was dried and concentrated by column chromatography to obtain intermediate VIII-2.

[0067] Example 3

[0068] The compound shown in formula VIII-3 was synthesized using the following synthetic route.

[0069] .

[0070] Synthesis of intermediate of formula II-1

[0071] Hydroquinone (10 mmol) was dissolved in N,N-dimethylformamide solution, potassium carbonate (15 mmol) was added, and the reaction was carried out at room temperature for half an hour. Then p-fluorobenzonitrile was added. The temperature was raised to 100 °C. The reaction was carried out for 3-4 hours. The reaction progress was monitored by TLC. After the reaction was completed, the solvent was removed. The remaining solid was dissolved in ethyl acetate and washed twice with saturated NaCl. The organic phase was collected, dried over anhydrous Na2SO4, and concentrated to give intermediate II-1.

[0072] Synthesis of intermediate of formula III-1

[0073] Intermediate II-1 (10 mmol) was dissolved in methanol, and an aqueous solution of sodium hydroxide (30 mmol) was added. The mixture was heated to reflux, and the reaction was monitored by TLC. After the reaction was complete, the solvent was evaporated, and the mixture was extracted with ethyl acetate. The aqueous phase was acidified with concentrated hydrochloric acid, and the pH was adjusted to 1-2. The mixture was then filtered to obtain intermediate III-1.

[0074] Synthesis of Formula V-3 intermediate

[0075] p-hydroxybenzaldehyde (10 mmol) was dissolved in tetrahydrofuran solution, and triethylamine (20 mmol) and N-methyl-N-isopropylchloroformamide (10 mmol) were added. The mixture was stirred at room temperature, and the reaction was monitored by TLC. After the reaction was completed, ethyl acetate was added, the mixture was filtered, and the filtrate was concentrated by rotary evaporation to obtain intermediate V-3.

[0076] Synthesis of Formula VI-3 intermediate

[0077] Intermediate V-3 (10 mmol) was dissolved in ultra-dry tetrahydrofuran solution, sodium borohydride (40 mmol) was added at 0 °C, and the reaction was heated to room temperature. The reaction progress was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers were combined, dried and concentrated, and column chromatography was used to obtain intermediate VI-3.

[0078] Synthesis of intermediates of formula VII-3

[0079] Intermediate VI-3 (10 mmol) was dissolved in tetrahydrofuran solution, carbon tetrabromide (15 mmol) was added, and triphenylphosphine (20 mmol) was added at 0 °C. The mixture was heated to room temperature and stirred. The reaction was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers were combined, dried and concentrated, and column chromatography was used to obtain intermediate VII-3.

[0080] Synthesis of Formula VIII-3 intermediate

[0081] Intermediate III-1 (2 mmol) was dissolved in N,N-dimethylformamide solution, sodium bicarbonate (3 mmol) was added, and the mixture was stirred at 70 °C for 10 minutes. The mixture was then cooled to 50 °C, and intermediate VII-3 (6 mmol) was added. The reaction was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, and the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, and the organic layers were combined. The mixture was dried and concentrated by column chromatography to obtain intermediate VIII-3.

[0082] Example 4

[0083] The compound shown in formula VIII-4 was synthesized using the following synthetic route.

[0084] .

[0085] Synthesis of intermediate of formula II-1

[0086] Hydroquinone (10 mmol) was dissolved in N,N-dimethylformamide solution, potassium carbonate (15 mmol) was added, and the reaction was carried out at room temperature for half an hour. Then p-fluorobenzonitrile was added. The temperature was raised to 100 °C. The reaction was carried out for 3-4 hours. The reaction progress was monitored by TLC. After the reaction was completed, the solvent was removed. The remaining solid was dissolved in ethyl acetate and washed twice with saturated NaCl. The organic phase was collected, dried over anhydrous Na2SO4, and concentrated to give intermediate II-1.

[0087] Synthesis of intermediate of formula III-1

[0088] Intermediate II-1 (10 mmol) was dissolved in methanol, and an aqueous solution of sodium hydroxide (30 mmol) was added. The mixture was heated to reflux, and the reaction was monitored by TLC. After the reaction was complete, the solvent was evaporated, and the mixture was extracted with ethyl acetate. The aqueous phase was acidified with concentrated hydrochloric acid, and the pH was adjusted to 1-2. The mixture was then filtered to obtain intermediate III-1.

[0089] Synthesis of Formula V-4 intermediate

[0090] p-hydroxybenzaldehyde (10 mmol) was dissolved in tetrahydrofuran solution, and triethylamine (20 mmol) and benzyl bromide (10 mmol) were added. The mixture was stirred at room temperature, and the reaction was monitored by TLC. After the reaction was completed, ethyl acetate was added, the mixture was filtered, and the filtrate was concentrated by rotary evaporation to obtain intermediate V-4.

[0091] Synthesis of Formula VI-4 intermediate

[0092] Intermediate V-4 (10 mmol) was dissolved in ultra-dry tetrahydrofuran solution, sodium borohydride (40 mmol) was added at 0 °C, and the reaction was heated to room temperature. The reaction progress was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers were combined, dried and concentrated by column chromatography to obtain intermediate VI-4.

[0093] Synthesis of intermediates of formula VII-4

[0094] Intermediate VI-4 (10 mmol) was dissolved in tetrahydrofuran solution, carbon tetrabromide (15 mmol) was added, and triphenylphosphine (20 mmol) was added at 0 °C. The mixture was heated to room temperature and stirred. The reaction was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers were combined, dried and concentrated, and column chromatography was used to obtain intermediate VII-4.

[0095] Synthesis of intermediate VIII-4

[0096] Intermediate III-1 (2 mmol) was dissolved in N,N-dimethylformamide solution, sodium bicarbonate (3 mmol) was added, and the mixture was stirred at 70 °C for 10 minutes. The mixture was then cooled to 50 °C, and intermediate VII-4 (6 mmol) was added. The reaction was monitored by TLC. After the reaction was completed, water was added, the solvent was evaporated, and the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, and the organic layers were combined. The mixture was dried and concentrated by column chromatography to obtain intermediate VIII-4.

[0097] The 4-(4-hydroxyphenoxy)benzoate derivatives of the present invention were synthesized according to the above method. Table 1 lists the structural characterization data of some compounds of the present invention.

[0098] Table 1 Physical properties and spectral characterization of the compounds

[0099]

[0100] Example 5:

[0101] Plate inhibition test: The compound was dissolved in DMSO and added to a quantitative PDA medium (20 g glucose, 200 g potato, 20 g agar, 1 L ultrapure water) to prepare plates with a final concentration of 50 μg / mL. Plates without the added drug served as blank controls, while fluopyram and flufenoxuron served as positive controls. Mycelial cakes were then inoculated into the center of each of the three types of plates. The inoculated plates were sealed with film and incubated at 25°C for 3-5 days. The colony diameter of the tested compound was calculated using the cross-cross method. The inhibition rate (%) was calculated using the following formula:

[0102]

[0103] Table 2 shows the inhibition rates of some compounds against plant pathogenic fungi (concentration: 100 µg / mL).

[0104]

[0105] The preliminary screening data above show that these compounds exhibit good fungicidal activity against all four pathogenic fungi. Among them, compounds ag, aj, am, cb, cl, and dc show particularly excellent inhibitory effects against wheat scab. Therefore, these compounds have promising application prospects.

[0106] Example 6:

[0107] To evaluate its field control efficacy, we conducted a two-year foliar spraying trial (100 μM NJU173, the aforementioned compound ag). This treatment consistently reduced symptoms of wheat scab on the ears, decreasing disease severity by 70%-75%. Figure 1 (a), and within two years, the accumulation of DON toxin was suppressed by 53%-60% ( Figure 1 (b) can recover 40%-42% of the production loss rate. Figure 1 (c) This demonstrates that NJU173 can effectively control Fusarium head blight and reduce DON pollution under field conditions.

[0108] We further evaluated the broad-spectrum control potential of NJU173 against Botrytis cinerea and Fusarium oxysporum. For example... Figure 1 As shown in Figure d, treatment with 50 μM NJU173 reduced the area of ​​gray mold lesions on mung bean leaves by more than 67%; similarly, this treatment significantly inhibited the symptoms of Fusarium wilt in tomato seedlings, reducing the disease index by approximately 53%. Figure 1 (d). It is worth noting that NJU173 did not show any visible phytotoxicity to mung bean and tomato plants. Figure 2 These results collectively demonstrate that NJU173 can effectively control Fusarium head blight and DON contamination under field conditions, and has broad-spectrum antifungal activity, showing its potential as a multifunctional crop protectant.

[0109] The TOR signaling pathway, as a core regulatory hub for nutrient sensing, metabolism, and fungal pathogenicity, is a highly promising antifungal target. While the natural TOR kinase inhibitor rapamycin exhibits antifungal activity in various fungi, its strong immunosuppressive effect on mammals hinders its direct application as an agricultural fungicide or in clinical antifungal therapy. Therefore, identifying fungal-specific targets within the TOR signaling pathway provides a new approach for developing novel antifungal agents that combine safety and selectivity. This invention reveals that the acetylation of the conserved lysine residues in the Sap protein of fungal pathogens acts as a TOR regulatory switch, driving successful fungal infection of the host by activating Sit4. A small molecule compound, ag (NJU173), specifically blocking Sap acetylation, was designed. This novel antifungal agent disrupts the TOR signaling pathway and prevents fungal infection. More importantly, ag (NJU173) effectively controlled Fusarium head blight in field trials and exhibited broad-spectrum activity against multiple fungal pathogens without affecting plant growth, thus establishing Sap acetylation as a selective and safe target for antifungal research.

[0110] In summary, the 4-(4-hydroxyphenoxy)benzoate derivatives described in this invention have the characteristics of simple structure, convenient preparation, novel mode of action, low toxicity, and high activity. They also exhibit good inhibitory effects on a variety of pathogenic fungi and are worthy of further research and development.

[0111] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A compound of a 4-(4-hydroxyphenoxy)benzoate derivative, characterized in that, It has the structure shown in equation (Ⅰ), in, A is C1-C 12 Alkyl and / or C1-C 12 Alkoxy-substituted and / or halogenated and / or N-substituted or unsubstituted five- or six-membered heterocycles, benzene rings or C3-C8 cycloalkyl groups; X is in any substitution position in A, and is an amide group or an amino group that is O, S, N-substituted or unsubstituted; B represents sulfonyl, sulfinyl, carbonyl, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 alkylamine, halogen-substituted C1-C12 alkyl, and S-substituted alkyl. Q represents H, halogen, hydroxyl, amino, cyano, nitro, phenyl, pyridyl, C1-C. 12 Alkyl groups, halogen-substituted C1-C 12 Alkyl, C1-C 12 Alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C1-C substituted with halogen and / or N-substituted 12 Alkoxy groups, composed of C1-C 12 Alkyl and / or C1-C 12 Alkoxy-substituted and / or halogenated and / or N-substituted or unsubstituted phenyl, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazole, C1-C 12 Alkyl and / or C1-C 12 Alkoxy-substituted and / or halogenated and / or N-substituted or unsubstituted C3-C8 heterocycles.

2. The compound according to claim 1, characterized in that, It is any one of the compounds shown in formula I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, I-10: X is O, B is CH2, and Q is Ph; X is O, B is CH2, and Q is 4-F-Ph; X is O, B is CH2, and Q is CH3NCH2(CH3)2; X is O, B is C=O, and Q is Ph; X is O, B is C=O, and Q is 4-F-Ph; X is O, B is C=O, and Q is CH3NCH2(CH3)2; X is O, B is SO2, and Q is Ph; X is O, B is SO2, and Q is 4-F-Ph; X is O, B is SO2, and Q is CH3NCH2(CH3)2; X is NH, B is CH2, and Q is Ph; X is NH, B is CH2, and Q is 4-F-Ph; X is NH, B is CH2, and Q is CH3NCH2(CH3)2; X is NH, B is C=O, and Q is Ph. X is NH, B is C=O, and Q is 4-F-Ph; X is NH, B is C=O, and Q is CH3NCH2(CH3)2; X is NH, B is SO2, and Q is Ph; X is NH, B is SO2, and Q is 4-F-Ph; X is NH, B is SO2, and Q is CH3NCH2(CH3)2; X is NCH3, B is CH2, and Q is Ph; X is NCH3, B is CH2, and Q is 4-F-Ph; X is NCH3, B is CH2, and Q is CH3NCH2(CH3)2; X is NCH3, B is C=O, and Q is Ph; X is NCH3, B is C=O, and Q is 4-F-Ph; X is NCH3, B is C=O, and Q is CH3NCH2(CH3)2; X is NCH3, B is SO2, and Q is Ph; X is NCH3, B is SO2, and Q is 4-F-Ph; X is NCH3, B is SO2, and Q is CH3NCH2(CH3)2; X is O, B is CH2, and Q is Ph; X is O, B is CH2, and Q is 4-F-Ph; X is O, B is CH2, and Q is CH3NCH2(CH3)2; X is O, B is C=O, and Q is Ph; X is O, B is C=O, and Q is 4-F-Ph; X is O, B is C=O, and Q is CH3NCH2(CH3)2; X is O, B is SO2, and Q is Ph; X is O, B is SO2, and Q is 4-F-Ph; X is O, B is SO2, and Q is CH3NCH2(CH3)2; X is NH, B is CH2, and Q is Ph; X is NH, B is CH2, and Q is 4-F-Ph; X is NH, B is CH2, and Q is CH3NCH2(CH3)2; X is NH, B is C=O, and Q is Ph. X is NH, B is C=O, and Q is 4-F-Ph; X is NH, B is C=O, and Q is CH3NCH2(CH3)2; X is NH, B is SO2, and Q is Ph; X is NH, B is SO2, and Q is 4-F-Ph; X is NH, B is SO2, and Q is CH3NCH2(CH3)2; X is NCH3, B is CH2, and Q is Ph; X is NCH3, B is CH2, and Q is 4-F-Ph; X is NCH3, B is CH2, and Q is CH3NCH2(CH3)2; X is NCH3, B is C=O, and Q is Ph; X is NCH3, B is C=O, and Q is 4-F-Ph; X is NCH3, B is C=O, and Q is CH3NCH2(CH3)2; X is NCH3, B is SO2, and Q is Ph; X is NCH3, B is SO2, and Q is 4-F-Ph; X is NCH3, B is SO2, and Q is CH3NCH2(CH3)2; X is O, B is CH2, and Q is Ph; X is O, B is CH2, and Q is 4-F-Ph; X is O, B is CH2, and Q is CH3NCH2(CH3)2; X is O, B is C=O, and Q is Ph; X is O, B is C=O, and Q is 4-F-Ph; X is O, B is C=O, and Q is CH3NCH2(CH3)2; X is O, B is SO2, and Q is Ph; X is O, B is SO2, and Q is 4-F-Ph; X is O, B is SO2, and Q is CH3NCH2(CH3)2; X is NH, B is CH2, and Q is Ph; X is NH, B is CH2, and Q is 4-F-Ph; X is NH, B is CH2, and Q is CH3NCH2(CH3)2; X is NH, B is C=O, and Q is Ph. X is NH, B is C=O, and Q is 4-F-Ph; X is NH, B is C=O, and Q is CH3NCH2(CH3)2; X is NH, B is SO2, and Q is Ph; X is NH, B is SO2, and Q is 4-F-Ph; X is NH, B is SO2, and Q is CH3NCH2(CH3)2; X is NCH3, B is CH2, and Q is Ph; X is NCH3, B is CH2, and Q is 4-F-Ph; X is NCH3, B is CH2, and Q is CH3NCH2(CH3)2; X is NCH3, B is C=O, and Q is Ph; X is NCH3, B is C=O, and Q is 4-F-Ph; X is NCH3, B is C=O, and Q is CH3NCH2(CH3)2; X is NCH3, B is SO2, and Q is Ph; X is NCH3, B is SO2, and Q is 4-F-Ph; X is NCH3, B is SO2, and Q is CH3NCH2(CH3)2; X is O, B is CH2, and Q is Ph; X is O, B is CH2, and Q is 4-F-Ph; X is O, B is CH2, and Q is CH3NCH2(CH3)2; X is O, B is C=O, and Q is Ph; X is O, B is C=O, and Q is 4-F-Ph; X is O, B is C=O, and Q is CH3NCH2(CH3)2; X is O, B is SO2, and Q is Ph; X is O, B is SO2, and Q is 4-F-Ph; X is O, B is SO2, and Q is CH3NCH2(CH3)2; X is NH, B is CH2, and Q is Ph; X is NH, B is CH2, and Q is 4-F-Ph; X is NH, B is CH2, and Q is CH3NCH2(CH3)2; X is NH, B is C=O, and Q is Ph. X is NH, B is C=O, and Q is 4-F-Ph; X is NH, B is C=O, and Q is CH3NCH2(CH3)2; X is NH, B is SO2, and Q is Ph; X is NH, B is SO2, and Q is 4-F-Ph; X is NH, B is SO2, and Q is CH3NCH2(CH3)2; X is NCH3, B is CH2, and Q is Ph; X is NCH3, B is CH2, and Q is 4-F-Ph; X is NCH3, B is CH2, and Q is CH3NCH2(CH3)2; X is NCH3, B is C=O, and Q is Ph; X is NCH3, B is C=O, and Q is 4-F-Ph; X is NCH3, B is C=O, and Q is CH3NCH2(CH3)2; X is NCH3, B is SO2, and Q is Ph; X is NCH3, B is SO2, and Q is 4-F-Ph; X is NCH3, B is SO2, and Q is CH3NCH2(CH3)2; X is O, B is CH2, and Q is Ph; X is O, B is CH2, and Q is 4-F-Ph; X is O, B is CH2, and Q is CH3NCH2(CH3)2; X is O, B is C=O, and Q is Ph; X is O, B is C=O, and Q is 4-F-Ph; X is O, B is C=O, and Q is CH3NCH2(CH3)2; X is O, B is SO2, and Q is Ph; X is O, B is SO2, and Q is 4-F-Ph; X is O, B is SO2, and Q is CH3NCH2(CH3)2; X is NH, B is CH2, and Q is Ph; X is NH, B is CH2, and Q is 4-F-Ph; X is NH, B is CH2, and Q is CH3NCH2(CH3)2; X is NH, B is C=O, and Q is Ph. X is NH, B is C=O, and Q is 4-F-Ph; X is NH, B is C=O, and Q is CH3NCH2(CH3)2; X is NH, B is SO2, and Q is Ph; X is NH, B is SO2, and Q is 4-F-Ph; X is NH, B is SO2, and Q is CH3NCH2(CH3)2; X is NCH3, B is CH2, and Q is Ph; X is NCH3, B is CH2, and Q is 4-F-Ph; X is NCH3, B is CH2, and Q is CH3NCH2(CH3)2; X is NCH3, B is C=O, and Q is Ph; X is NCH3, B is C=O, and Q is 4-F-Ph; X is NCH3, B is C=O, and Q is CH3NCH2(CH3)2; X is NCH3, B is SO2, and Q is Ph; X is NCH3, B is SO2, and Q is 4-F-Ph; X is NCH3, B is SO2, and Q is CH3NCH2(CH3)2; X is O, B is CH2, and Q is Ph; X is O, B is CH2, and Q is 4-F-Ph; X is O, B is CH2, and Q is CH3NCH2(CH3)2; X is O, B is C=O, and Q is Ph; X is O, B is C=O, and Q is 4-F-Ph; X is O, B is C=O, and Q is CH3NCH2(CH3)2; X is O, B is SO2, and Q is Ph; X is O, B is SO2, and Q is 4-F-Ph; X is O, B is SO2, and Q is CH3NCH2(CH3)2; X is NH, B is CH2, and Q is Ph; X is NH, B is CH2, and Q is 4-F-Ph; X is NH, B is CH2, and Q is CH3NCH2(CH3)2; X is NH, B is C=O, and Q is Ph. X is NH, B is C=O, and Q is 4-F-Ph; X is NH, B is C=O, and Q is CH3NCH2(CH3)2; X is NH, B is SO2, and Q is Ph; X is NH, B is SO2, and Q is 4-F-Ph; X is NH, B is SO2, and Q is CH3NCH2(CH3)2; X is NCH3, B is CH2, and Q is Ph; X is NCH3, B is CH2, and Q is 4-F-Ph; X is NCH3, B is CH2, and Q is CH3NCH2(CH3)2; X is NCH3, B is C=O, and Q is Ph; X is NCH3, B is C=O, and Q is 4-F-Ph; X is NCH3, B is C=O, and Q is CH3NCH2(CH3)2; X is NCH3, B is SO2, and Q is Ph; X is NCH3, B is SO2, and Q is 4-F-Ph; X is NCH3, B is SO2, and Q is CH3NCH2(CH3)2; X is O, B is CH2, and Q is Ph; X is O, B is CH2, and Q is 4-F-Ph; X is O, B is CH2, and Q is CH3NCH2(CH3)2; X is O, B is C=O, and Q is Ph; X is O, B is C=O, and Q is 4-F-Ph; X is O, B is C=O, and Q is CH3NCH2(CH3)2; X is O, B is SO2, and Q is Ph; X is O, B is SO2, and Q is 4-F-Ph; X is O, B is SO2, and Q is CH3NCH2(CH3)2; X is NH, B is CH2, and Q is Ph; X is NH, B is CH2, and Q is 4-F-Ph; X is NH, B is CH2, and Q is CH3NCH2(CH3)2; X is NH, B is C=O, and Q is Ph. X is NH, B is C=O, and Q is 4-F-Ph; X is NH, B is C=O, and Q is CH3NCH2(CH3)2; X is NH, B is SO2, and Q is Ph; X is NH, B is SO2, and Q is 4-F-Ph; X is NH, B is SO2, and Q is CH3NCH2(CH3)2; X is NCH3, B is CH2, and Q is Ph; X is NCH3, B is CH2, and Q is 4-F-Ph; X is NCH3, B is CH2, and Q is CH3NCH2(CH3)2; X is NCH3, B is C=O, and Q is Ph; X is NCH3, B is C=O, and Q is 4-F-Ph; X is NCH3, B is C=O, and Q is CH3NCH2(CH3)2; X is NCH3, B is SO2, and Q is Ph; X is NCH3, B is SO2, and Q is 4-F-Ph; X is NCH3, B is SO2, and Q is CH3NCH2(CH3)2; X is O, B is CH2, and Q is Ph; X is O, B is CH2, and Q is 4-F-Ph; X is O, B is CH2, and Q is CH3NCH2(CH3)2; X is O, B is C=O, and Q is Ph; X is O, B is C=O, and Q is 4-F-Ph; X is O, B is C=O, and Q is CH3NCH2(CH3)2; X is O, B is SO2, and Q is Ph; X is O, B is SO2, and Q is 4-F-Ph; X is O, B is SO2, and Q is CH3NCH2(CH3)2; X is NH, B is CH2, and Q is Ph; X is NH, B is CH2, and Q is 4-F-Ph; X is NH, B is CH2, and Q is CH3NCH2(CH3)2; X is NH, B is C=O, and Q is Ph. X is NH, B is C=O, and Q is 4-F-Ph; X is NH, B is C=O, and Q is CH3NCH2(CH3)2; X is NH, B is SO2, and Q is Ph; X is NH, B is SO2, and Q is 4-F-Ph; X is NH, B is SO2, and Q is CH3NCH2(CH3)2; X is NCH3, B is CH2, and Q is Ph; X is NCH3, B is CH2, and Q is 4-F-Ph; X is NCH3, B is CH2, and Q is CH3NCH2(CH3)2; X is NCH3, B is C=O, and Q is Ph; X is NCH3, B is C=O, and Q is 4-F-Ph; X is NCH3, B is C=O, and Q is CH3NCH2(CH3)2; X is NCH3, B is SO2, and Q is Ph; X is NCH3, B is SO2, and Q is 4-F-Ph; X is NCH3, B is SO2, and Q is CH3NCH2(CH3)2; X is O, B is CH2, and Q is Ph; X is O, B is CH2, and Q is 4-F-Ph; X is O, B is CH2, and Q is CH3NCH2(CH3)2; X is O, B is C=O, and Q is Ph; X is O, B is C=O, and Q is 4-F-Ph; X is O, B is C=O, and Q is CH3NCH2(CH3)2; X is O, B is SO2, and Q is Ph; X is O, B is SO2, and Q is 4-F-Ph; X is O, B is SO2, and Q is CH3NCH2(CH3)2; X is NH, B is CH2, and Q is Ph; X is NH, B is CH2, and Q is 4-F-Ph; X is NH, B is CH2, and Q is CH3NCH2(CH3)2; X is NH, B is C=O, and Q is Ph. X is NH, B is C=O, and Q is 4-F-Ph; X is NH, B is C=O, and Q is CH3NCH2(CH3)2; X is NH, B is SO2, and Q is Ph; X is NH, B is SO2, and Q is 4-F-Ph; X is NH, B is SO2, and Q is CH3NCH2(CH3)2; X is NCH3, B is CH2, and Q is Ph; X is NCH3, B is CH2, and Q is 4-F-Ph; X is NCH3, B is CH2, and Q is CH3NCH2(CH3)2; X is NCH3, B is C=O, and Q is Ph; X is NCH3, B is C=O, and Q is 4-F-Ph; X is NCH3, B is C=O, and Q is CH3NCH2(CH3)2; X is NCH3, B is SO2, and Q is Ph; X is NCH3, B is SO2, and Q is 4-F-Ph; X is NCH3, B is SO2, and Q is CH3NCH2(CH3)2; X is O, B is CH2, and Q is Ph; X is O, B is CH2, and Q is 4-F-Ph; X is O, B is CH2, and Q is CH3NCH2(CH3)2; X is O, B is C=O, and Q is Ph; X is O, B is C=O, and Q is 4-F-Ph; X is O, B is C=O, and Q is CH3NCH2(CH3)2; X is O, B is SO2, and Q is Ph; X is O, B is SO2, and Q is 4-F-Ph; X is O, B is SO2, and Q is CH3NCH2(CH3)2; X is NH, B is CH2, and Q is Ph; X is NH, B is CH2, and Q is 4-F-Ph; X is NH, B is CH2, and Q is CH3NCH2(CH3)2; X is NH, B is C=O, and Q is Ph. X is NH, B is C=O, and Q is 4-F-Ph; X is NH, B is C=O, and Q is CH3NCH2(CH3)2; X is NH, B is SO2, and Q is Ph; X is NH, B is SO2, and Q is 4-F-Ph; X is NH, B is SO2, and Q is CH3NCH2(CH3)2; X is NCH3, B is CH2, and Q is Ph; X is NCH3, B is CH2, and Q is 4-F-Ph; X is NCH3, B is CH2, and Q is CH3NCH2(CH3)2; X is NCH3, B is C=O, and Q is Ph; X is NCH3, B is C=O, and Q is 4-F-Ph; X is NCH3, B is C=O, and Q is CH3NCH2(CH3)2; X is NCH3, B is SO2, and Q is Ph; X is NCH3, B is SO2, and Q is 4-F-Ph; X is NCH3, B is SO2, and Q is CH3NCH2(CH3)2.

3. The method for preparing the compound according to claim 1 or 2, characterized in that, The following synthetic route was used for its synthesis, wherein the position and type of substituents were changed according to the specific compound being prepared:

4. The preparation method according to claim 3, characterized in that, In step a, raw material I and alkali are dissolved in a solvent, p-fluorobenzonitrile is added, and the mixture is stirred at 0℃-110℃. After the reaction is complete, dilute hydrochloric acid is added to quench the reaction, followed by extraction, washing with saturated sodium chloride solution, combining the organic layers, drying and concentrating to obtain intermediate II. In step b, intermediate II is dissolved in a solvent, an aqueous solution of alkali is added, and the mixture is stirred at 0℃-90℃. After the reaction is complete, the solvent is evaporated to dryness, and the mixture is extracted with ethyl acetate. The aqueous phase is acidified with concentrated hydrochloric acid and filtered to obtain intermediate III. In step c, raw material IV is dissolved in a solvent, alkali is added, and the mixture is stirred at 0℃-90℃. After the reaction is complete, the solvent is evaporated, the mixture is extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers are combined, dried, concentrated, and column chromatography is used to obtain intermediate V. In step d, intermediate V is dissolved in a solvent, sodium borohydride is added, and the mixture is stirred at 0℃-90℃. After the reaction is complete, water is added, the solvent is evaporated, the mixture is extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers are combined, dried, concentrated, and column chromatography is used to obtain intermediate VI. In step e, intermediate VI is dissolved in a solvent, carbon tetrabromide and triphenylphosphine are added, and the mixture is stirred at room temperature until the reaction is complete. Water is added, the solvent is evaporated to dryness, the mixture is extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers are combined, dried, concentrated, and column chromatography is used to obtain intermediate VII. In step f, intermediate III is dissolved in a solvent, alkali is added, and the mixture is stirred at 50-90°C. Intermediate VII is then added, and after the reaction is complete, water is added, the solvent is evaporated, the mixture is extracted with ethyl acetate, washed with saturated sodium chloride solution, the organic layers are combined, and the mixture is dried and concentrated by column chromatography to obtain intermediate VII.

5. The preparation method according to claim 4, characterized in that, The solvent in step af is selected from water, N,N-dimethylformamide, acetonitrile, dichloromethane, 1,4-dioxane, toluene, dimethyl sulfoxide, acetic acid, tetrahydrofuran, methanol, ethanol, and acetone.

6. The use of the compound of claim 1 or 2 as a pesticide fungicide.

7. The application as described in claim 7, characterized in that, It is to prevent and control plant diseases caused by pathogenic fungi.

8. The application as described in claim 7, characterized in that, The pathogenic fungus is selected from at least one of the following: Alternaria solani (early blight pathogen of tomato); Botrytis cinerea (gray mold pathogen of tomato); Cercospora achidicola (brown spot pathogen of peanut); Fusarium graminearum (fusarium graminearum (wheat scab virgaurea)); Phytophthorainfestans (late blight pathogen of potato); Physalospora piricola (ring rot pathogen of apple); Rhizoctonia solani (sheath blight pathogen of rice); and Sclerotinia sclerotiorum (s ..."sclerotinia sclerotiorum'" (sclerotinia sclerotiorum ("sclerotinia sclerotiorum'" (sclerotinia sclerotiorum's sclerotiorum'" (sclerotiorum sclerotiorum's sclerotiorum'" (sclerotiorum sclerotiorum's sclerotiorum'" (sclerotiorum sclerotiorum's sclerotio 9. A pesticide fungicide, comprising an active ingredient and excipients, characterized in that, The active ingredient includes at least one of the compounds of claim 1 or 2, and the content of the active ingredient is 1 to 99.9999% by weight; preferably, the content of the active ingredient is 1 to 50% by weight.

10. The pesticide fungicide according to claim 9, characterized in that, The formulation of the pesticide fungicide is selected from one of the following: emulsifiable concentrate, suspension concentrate, wettable powder, powder, granule, aqueous solution, mother liquor, and mother powder.

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