Thiophene borate bactericide

Abstract

The invention provides a thiophene boric acid ester compound with a novel structure. The compound has a remarkable inhibition effect on spore germination and appressorium formation of various plant pathogenic fungi and oomycetes (such as pyricularia oryzae, colletotrichum, gibberellic disease bacteria, phytophthora and phytophthora capsici).

Description

Technical Field

[0001] This invention belongs to the field of bactericide technology, specifically relating to a thiophene borate ester bactericide. Background Technology

[0002] Most plant diseases are caused by fungi and oomycetes. A single plant may be affected by several or even dozens of different fungi and oomycetes causing diseases. For example, rice diseases such as sheath blight, rice blast, rice false smut, sesame leaf spot, and bakanae disease; wheat diseases such as Fusarium head blight, stripe rust, stem rust, leaf rust, and root rot; and corn diseases such as large leaf spot, small leaf spot, stem base rot, rust, sheath blight, Curvularia leaf spot, head smut, and powdery mildew are all caused by fungi. Potato late blight, soybean Phytophthora blight, pepper Phytophthora blight, grape downy mildew, and cucumber downy mildew are caused by oomycetes.

[0003] Chemical fungicides, characterized by their economy and high efficiency, have long been the preferred method for controlling crop diseases. Commonly used fungicides include cyazofamid, chlorothalonil, pyraclostrobin, chlorothalonil, thiophanate-methyl, carbendazim, azoxystrobin, boscalid, prochloraz, and mancozeb. However, these fungicides have exhibited a series of problems with increasing years of use. For example, they show varying degrees of toxicity to non-target organisms in the farmland environment; their similar and singular modes of action lead to field resistance; and cross-resistance among fungicides of the same class is a serious problem. Therefore, the development of novel, green, and safe fungicides is an urgent need for safe production.

[0004] Plant pathogens must spread to the plant body to cause primary infection, and secondary infection can only occur between plants through transmission. Asexual spore dispersal is the primary mode of transmission. For example, when *Pyrophyte oryzae* and *Anthracnose* infect plants, spores adhere to the plant surface and germinate into germ tubes. Appressoria then form at the tips of these germ tubes, and under significant turgor pressure, infection nails differentiate from the base of the appressoria, invading the plant tissue and causing disease. Currently, there are very few fungicides on the pesticide market that specifically inhibit spore germination and appressoria formation; only tricyclazole prevents disease by inhibiting the maturation of pathogen appressoria. Therefore, developing inhibitors targeting pathogen spore germination and appressoria formation could provide a new avenue for the development of novel fungicides. Summary of the Invention

[0005] This invention provides a novel thiophene borate ester compound that significantly inhibits the germination of conidia and the formation of appressorium by *Pyrrosia oryzae*, exhibiting significant preventive and therapeutic effects against pathogens such as rice blast. Furthermore, this compound also demonstrates significant control effects against various other plant pathogenic fungi and oomycetes.

[0006] This invention provides a thiophene borate ester compound of formula (I), its stereoisomers, racemates, tautomers, isotope labels, nitrogen oxides, agriculturally acceptable salts or esters, solvates, or solvates of agriculturally acceptable salts:

[0007]

[0008] in, This indicates that R1 and R2, together with the two O atoms attached to them and B, constitute an unsubstituted compound, or are optionally substituted by one, two or more R atoms. a The following groups are substituted: 5-12 membered heterocyclic groups or benzo5-12 membered heterocyclic groups;

[0009] The R a Selected from H, =O, C 1-12 Alkyl or halogenated C 1-12 alkyl;

[0010] R3 is selected from: H,

[0011] R4 is selected from: H,

[0012] R5 is selected from: H,

[0013] m is a natural number selected from 0 to 5;

[0014] R b They may be the same or different, and are independently selected from H, halogen, C1-6 alkyl, C1-6 alkoxy, cyano, hydroxyl, C1-6 alkyl ester, aldehyde, 5-10 heteroaryl, -OC 6-10 Aryl;

[0015] The C1-6 alkyl, C1-6 alkoxy, and C1-6 alkyl ester groups are unsubstituted or optionally substituted with one, two, or more halogens;

[0016] The 5-10 quinone heteroaryl group, -OC 6-10 The aryl group is unsubstituted, or optionally substituted with one, two or more halogens or C1-6 alkyl groups;

[0017] R3, R4, and R5 are not all H at the same time.

[0018] According to an embodiment of the present invention, This indicates that R1 and R2, together with the two O atoms attached to them and B, constitute an unsubstituted compound, or are optionally substituted by one, two or more R atoms. a The following groups are substituted: 5-10 membered heterocyclic groups or benzo5-10 membered heterocyclic groups;

[0019] Preferably, This indicates that R1 and R2, together with the two O atoms attached to them and B, form the following groups: m is a natural number between 0 and 4; * indicates the linking site of a group.

[0020] According to an embodiment of the present invention, This indicates that R1 and R2, together with the two O atoms attached to them and B, form the following groups:

[0021] According to an embodiment of the present invention, R a They may be the same or different, and are independently selected from H, =O, C1-6 alkyl, and halo-C1-6 alkyl; preferably, R a They may be the same or different, and are independently selected from H, =O, C1-4 alkyl, and halo-C1-4 alkyl; for example, R a They may be the same or different, and are independently selected from H, =O, methyl, ethyl, n-propyl, isopropyl, n-butyl, or tert-butyl.

[0022] According to an embodiment of the present invention, R3 is selected from: H,

[0023] m is a natural number selected from 0 to 5;

[0024] R b They may be the same or different, and are independently selected from H, halogen, C1-6 alkyl, C1-6 alkoxy, cyano, hydroxyl, C1-6 alkyl ester, aldehyde, 5-10 heteroaryl, -OC 6-10 Aryl;

[0025] The C1-6 alkyl, C1-6 alkoxy, and C1-6 alkyl ester groups are unsubstituted or optionally substituted with one, two, or more halogens;

[0026] The 5-10 quinone heteroaryl group, -OC 6-10 The aryl group is unsubstituted, or optionally substituted with one, two or more halogens or C1-6 alkyl groups;

[0027] Preferably, the 5-10 member heteroaryl group is selected from: piperidinyl, piperazineyl;

[0028] Preferably, -OC 6-10 The aryl group is selected from: -O-phenyl, -O-naphthyl.

[0029] According to an embodiment of the present invention, R3 is selected from H,

[0030] R bThey may be the same or different, and are independently selected from H, halogen, C1-6 alkyl, C1-6 alkoxy, cyano, hydroxyl, C1-6 alkyl ester, and aldehyde.

[0031] The C1-6 alkyl, C1-6 alkoxy, and C1-6 alkyl ester groups are unsubstituted or optionally substituted with one, two, or more halogens;

[0032] m is a natural number selected from 0 to 5;

[0033] Preferably, R b They may be the same or different, and are independently selected from H, halogen, C1-4 alkyl, C1-4 alkoxy, cyano, hydroxyl, C1-4 alkyl ester, and aldehyde; the C1-4 alkyl, C1-4 alkoxy, and C1-4 alkyl ester groups are unsubstituted or optionally substituted by one, two, or more halogens.

[0034] For example, R3 is selected from: H,

[0035] According to an embodiment of the present invention, R4 is selected from: H,

[0036] m is a natural number selected from 0 to 5;

[0037] R b They may be the same or different, and are independently selected from H, halogen, C1-6 alkyl, C1-6 alkoxy, cyano, and hydroxyl.

[0038] The C1-6 alkyl and C1-6 alkoxy groups are unsubstituted or optionally substituted with one, two or more halogens;

[0039] Preferably, R b They may be the same or different, and are independently selected from H, halogen, C1-4 alkyl, C1-4 alkoxy, cyano, and hydroxyl; the C1-4 alkyl and C1-4 alkoxy are unsubstituted or optionally substituted by one, two, or more halogens;

[0040] For example, R4 is selected from: H,

[0041] According to an embodiment of the present invention, R5 is selected from: H,

[0042] m is a natural number selected from 0 to 5;

[0043] R b They may be the same or different, and are independently selected from H, halogen, C1-6 alkyl, C1-6 alkoxy, cyano, and hydroxyl.

[0044] The C1-6 alkyl and C1-6 alkoxy groups are unsubstituted or optionally substituted with one, two or more halogens;

[0045] Preferably, R b They may be the same or different, and are independently selected from H, halogen, C1-4 alkyl, C1-4 alkoxy, cyano, and hydroxyl; the C1-4 alkyl and C1-4 alkoxy are unsubstituted or optionally substituted by one, two, or more halogens;

[0046] For example, R5 is selected from: H,

[0047] According to an embodiment of the present invention, the compound is selected from compounds represented by the following formula (I-1):

[0048]

[0049] in, R3 has the above definition.

[0050] According to an embodiment of the present invention, the compound is selected from compounds represented by the following formula (I-2):

[0051]

[0052] in, R4 has the above definition.

[0053] According to an embodiment of the present invention, the compound is selected from compounds represented by the following formula (I-3):

[0054]

[0055] in, R5 has the above definition.

[0056] According to an embodiment of the present invention, the compound is selected from the following compounds:

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064] The present invention also provides a method for preparing the above-mentioned compound, its stereoisomers, racemates, tautomers, isotope labels, nitrogen oxides, agriculturally acceptable salts or esters, solvates, or solvates of agriculturally acceptable salts, wherein the preparation method comprises the following steps:

[0065] The compound shown in formula (Ia) reacts with R3-Bpin and / or R4-Bpin and / or R5-Bpin to give the compound shown in formula (I);

[0066] The reaction formula is as follows:

[0067]

[0068] in, R3, R4, and R5 have the definitions described above;

[0069] X is selected from halogens (such as fluorine, chlorine, bromine, iodine);

[0070] Bpin represents pinacol borate ester.

[0071] According to an embodiment of the present invention, the reaction is carried out in a catalyst; the catalyst is preferably DPPF palladium dichloride.

[0072] According to an embodiment of the present invention, the reaction is carried out in the presence of a base; the base is preferably an inorganic base, such as potassium phosphate.

[0073] According to an embodiment of the present invention, the reaction is carried out in a solvent; the solvent is preferably a mixture of tetrahydrofuran and water.

[0074] According to an embodiment of the present invention, formula (Ia) can be prepared by the following method:

[0075] The compound shown in formula (Ib) reacts with the compound shown in formula (Ic) to give the compound shown in formula (Ia);

[0076] The reaction formula is as follows:

[0077]

[0078] in, It has the definition described above;

[0079] X is selected from halogens (such as fluorine, chlorine, bromine, iodine).

[0080] According to an embodiment of the present invention, the reaction is carried out in a solvent; the solvent is preferably toluene.

[0081] The present invention also provides a pesticide composition comprising the above-mentioned compound, its stereoisomer, racemate, tautomer, isotope label, nitrogen oxide, agriculturally acceptable salt or ester, solvate, or a solvate of an agriculturally acceptable salt.

[0082] According to an embodiment of the invention, the pesticide composition is, for example, a fungicide.

[0083] The present invention also provides the use of the above-described compounds, their stereoisomers, racemates, tautomers, isotope labels, nitrogen oxides, agriculturally acceptable salts or esters, solvates or solvates of agriculturally acceptable salts, or the above-described compositions in the preparation of fungicides.

[0084] According to an embodiment of the present invention, the fungicide is used in the agronomic field (agricultural fungicide) or the horticultural field (horticultural fungicide).

[0085] According to embodiments of the present invention, the fungicide inhibits the germination of fungal and / or oomycete spores and the formation of appressoriums, and prevents plant diseases caused by fungi and / or oomycetes.

[0086] This invention also provides the use of the above-mentioned compounds, their stereoisomers, racemates, tautomers, isotopic markers, nitrogen oxides, agriculturally acceptable salts or esters, solvates, or solvates of agriculturally acceptable salts, or combinations thereof, for the prevention and control of plant diseases caused by fungi and / or oomycetes. According to embodiments of the invention, the fungus is at least one of *Pyrophyte oryzae*, *Anthracnose*, *Fusarium graminearum*, *Phytophthora capsici*, and *Phytophthora capsici*.

[0087] According to embodiments of the present invention, the plant diseases caused by the fungi and / or oomycetes are selected from the following: rice sheath blight, rice blast, rice false smut, sesame spot, and bakanae disease; wheat scab, stripe rust, stem rust, leaf rust, root rot, and sheath blight; maize large leaf spot, small leaf spot, anthracnose, stem base rot, rust, sheath blight, Curvularia leaf spot, common smut, and powdery mildew; mango anthracnose, potato late blight, soybean Phytophthora blight, pepper Phytophthora blight, grape downy mildew, and cucumber downy mildew.

[0088] To achieve the desired effect, the amount of compound used varies depending on various factors, such as the compound used, the crop being protected, the type of pest, the degree of infection, climatic conditions, the application method, and the formulation used.

[0089] The selection of dosage forms or compositional components described herein should be consistent with the physical properties of the active ingredient, the method of application, and environmental factors such as soil type, humidity, and temperature.

[0090] The dosage forms of the compounds or compositions include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and / or suspensions), etc., which may optionally be thickened into a gel. The dosage forms also include solids such as powders, granules, tablets, pills, films, etc., which may be water-dispersible (“wettable”) or water-soluble. The active ingredient may be microencapsulated and re-formed into a suspension or solid dosage form; alternatively, the entire dosage form of the active ingredient may be encapsulated. Encapsulation can control or delay the release of the active ingredient. Sprayable formulations can be diluted in a suitable medium, using a spray volume of approximately one hundred to several hundred liters per hectare. High-concentration compositions are primarily used as intermediates for further processing.

[0091] All formulations may contain small amounts of additives to reduce foaming, prevent clumping, prevent corrosion, and inhibit microbial growth, or thickeners to increase viscosity. Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, sulfonated dialkyl succinates, alkyl sulfates, alkylbenzene sulfonates, organosilanes, N,N-dialkyl taurates, lignin sulfonates, naphthalene sulfonates with aldehyde condensates, polycarboxylate esters, and polyoxyethylene / polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, magnesia, and kaolin; starch; sugar; silica; talc; diatomaceous earth; urea; calcium carbonate; sodium carbonate; sodium bicarbonate; and sodium sulfate. Liquid diluents include, for example, water; N,N-dimethylformamide; dimethyl sulfone; N-alkylpyrrolidone; ethylene glycol; polypropylene glycol; paraffin; alkylbenzene; alkylnaphthalene; olive oil; castor oil; linseed oil; tung oil; sesame oil; corn oil; peanut oil; cottonseed oil; soybean oil; rapeseed oil; and cocoa butter; fatty acid esters; ketones such as cyclohexanone, 2-heptanone, isophorone, and 4-hydroxy-4-methyl-2-pentanone; and alcohols such as methanol, cyclohexanol, dodecyl alcohol, and tetrahydrofuranol. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the components. Powders and fine powders can be prepared by mixing or, typically, by grinding in a hammer mill or hydraulic mill.

[0092] In this article, for certain applications of the composition, such as in agriculture, one, two or more other fungicides, insecticides, acaricides, herbicides, plant growth regulators or fertilizers may be added to the composition of the present invention, thereby producing additional advantages and effects.

[0093] Beneficial effects

[0094] This invention provides a novel thiophene borate ester compound that significantly inhibits spore germination and appressorium formation of various plant pathogenic fungi and oomycetes (e.g., *Pseudomonas aeruginosa*, *Amycosis anthracnose*, *Fusarium graminearum*, *Phytophthora capsici*, and *Phytophthora capsici*). Furthermore, this invention demonstrates its efficacy through indoor potted plant inoculation experiments.

[0095] Terminology Definitions and Explanations

[0096] In some substituents Or, the "*" indicates a connection point.

[0097] "More than" means three or more, such as 3, 4, 5 or 6.

[0098] In this document, the term "halogen" refers to fluorine, chlorine, bromine, and / or iodine. Correspondingly, the term "halogenated" refers to fluorination, chlorination, bromination, and / or iodination. Within the scope of this document, when an atom, residue, group, or part is halogenated, the atom at the halogenated position can be monosubstituted, disubstituted, or polysubstituted up to fully substituted by the halogen atom, for example, "halogenated C..." 1-12 Alkyl and Halogenated C 1-12 Alkoxy groups, etc.

[0099] Term "C" 1-12 "alkyl" should be understood to refer to a straight-chain or branched saturated monovalent hydrocarbon group having 1 to 12 carbon atoms, preferably C12. 1-10 Alkyl or C 1-6 Alkyl group. "C" 1-6 "alkyl" should be understood to preferably represent a straight-chain or branched saturated monovalent hydrocarbon group having 1, 2, 3, 4, 5, or 6 carbon atoms. The alkyl group is, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-methylbutyl, 1-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, neopentyl, 1,1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 2,3-dimethylbutyl, 1,3-dimethylbutyl, or 1,2-dimethylbutyl, or their isomers. In particular, the group has 1, 2, or 3 carbon atoms ("C..."). 1-3 Alkyl), such as methyl, ethyl, n-propyl or isopropyl.

[0100] The term "5-12 membered heterocyclic group" refers to a saturated or partially saturated monovalent monocyclic or bicyclic hydrocarbon ring containing 1-5, preferably 1-3, heteroatoms selected from N, O, and S. The heterocyclic group can be connected to the rest of the molecule via any one of the carbon atoms or a nitrogen atom (if present). Specifically, the heterocyclic group can include, but is not limited to: 4-membered rings, such as azirrobutyl or oxobutyl; 5-membered rings, such as tetrahydrofuranyl, dioxacyclopentenyl, pyrrolyl, imidazoalkyl, pyrazolyl, or pyrrololinyl; or 6-membered rings, such as tetrahydropyranyl, piperidinyl, morpholinyl, dithiaalkyl, thiomorpholinyl, piperazinyl, or trithiaalkyl; or 7-membered rings, such as diazacycloheptyl. Optionally, the heterocyclic group can be benzofused. The heterocyclic group may be bicyclic, such as, but not limited to, a 5,5-membered ring, like a hexahydrocyclopentano[c]pyrrolo-2(1H)-yl ring, or a 5,6-membered bicyclic ring, like a hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl ring. The nitrogen-containing ring may be partially unsaturated, i.e., it may contain one or more double bonds, such as, but not limited to, 2,5-dihydro-1H-pyrroloyl, 4H-[1,3,4]thiadiazinyl, 4,5-dihydrooxazolyl, or 4H-[1,4]thiazinyl, or it may be benzofused, such as, but not limited to, dihydroisoquinolinyl.

[0101] The above refers to the term "C" 1-12 The definition of "alkyl" also applies to compounds containing "C". 1-12 Other terms for "alkyl", such as the term "halogenated C", 1-12 "alkyl" or "C" 1-12 "alkoxy" or "halogenated C" 1-12 "Alkyloxy" etc.

[0102] "Stereoisomers" are compounds that have the same chemical structure but whose atoms or groups are arranged differently in space. Stereoisomers include enantiomers, diastereomers, conformational isomers (rotational isomers), geometric isomers (cis / trans) isomers, and hindered isomers, etc.

[0103] "Tautomers" refer to structural isomers with different energies that can interconvert through a low energy barrier. If tautomerism is possible (e.g., in solution), chemical equilibrium can be achieved for the tautomers. For example, proton tautomers (also called prototropic tautomers) involve interconversions via proton migration, such as keto-enol isomerization and imine-enamine isomerization. Valence tautomers involve interconversions via the rearrangement of some bonding electrons. A specific example of a keto-enol tautomer is the interconversion between pentane-2,4-dione and 4-hydroxypent-3-en-2-one. Another example of tautomerism is phenol-keto tautomerism. A specific example of a phenol-keto tautomer is the interconversion between pyridine-4-ol and pyridine-4(1H)-keto. Unless otherwise stated, all tautomer forms of the compounds of this invention are within the scope of this invention.

[0104] The term "nitrogen oxide" in this invention refers to an N-oxide formed by oxidizing one or more nitrogen atoms when the compound contains several amine functional groups. Specific examples of N-oxides are N-oxides of tertiary amines or N-oxides containing nitrogen atoms in nitrogen-containing heterocyclic nitrogen atoms. The corresponding amines can be treated with oxidizing agents such as hydrogen peroxide or peracids (e.g., peroxycarboxylic acids) to form N-oxides (see Advanced Organic Chemistry, Wiley Interscience, 4th edition, Jerry March, pages). In particular, N-oxides can be prepared using the LWDeady method (Syn. Comm. 1977, 7, 509-514), wherein the amine compound is reacted with m-chloroperoxybenzoic acid (MCPBA), for example in an inert solvent such as dichloromethane.

[0105] As used in this invention, the term "metabolite" refers to the product obtained in vivo through the metabolism of a specific compound or its salt. A metabolite of a compound can be identified using techniques known in the art, and its activity can be characterized by experimental methods as described in this invention. Such products can be obtained by administering the compound through oxidation, reduction, hydrolysis, acylation, deacylation, esterification, defatting, enzymatic cleavage, etc. Accordingly, this invention includes metabolites of compounds, including metabolites produced by sufficiently exposing the compounds of this invention to mammals for a period of time.

[0106] Agriculturally acceptable salts can be, for example, acid addition salts of compounds of the present invention having sufficient basicity and containing nitrogen atoms in the chain or ring, such as acid addition salts formed with inorganic acids including: hydrochloric acid, hydrofluoric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, pyrosulfuric acid, phosphoric acid or nitric acid, or bisulfate; or acid addition salts formed with organic acids including: formic acid, acetic acid, acetoacetic acid, pyruvic acid, trifluoroacetic acid, propionic acid, butyric acid, hexanoic acid, heptanoic acid, undecanoic acid, lauric acid, benzoic acid, salicylic acid, 2-(4-hydroxybenzoyl)benzoic acid, camphoric acid, cinnamic acid, cyclopentanepropionic acid, and diglucose. Gluconic acid, 3-hydroxy-2-naphtholic acid, nicotinic acid, pyruvic acid, pectinic acid, persulfate, 3-phenylpropionic acid, picric acid, pentyl acid, 2-hydroxyethanesulfonic acid, itaconic acid, aminosulfonic acid, trifluoromethanesulfonic acid, dodecyl sulfuric acid, ethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, 2-naphthalenesulfonic acid, naphthalenedisulfonic acid, camphorsulfonic acid, citric acid, tartaric acid, stearic acid, lactic acid, oxalic acid, malonic acid, succinic acid, malic acid, adipic acid, alginic acid, maleic acid, fumaric acid, D-gluconic acid, mandelic acid, ascorbic acid, glucohepanoic acid, glycerophosphate, aspartic acid, sulfosalicylic acid, hemisulfonic acid or thiocyanate.

[0107] Alternatively, another suitable agriculturally acceptable salt of the compounds of the present invention having sufficient acidity is an alkali metal salt (e.g., sodium or potassium salt), an alkaline earth metal salt (e.g., calcium or magnesium salt), an ammonium salt, or a salt formed with an organic base that provides a physiologically acceptable cation, such as a salt formed with sodium ions, potassium ions, N-methylglucosamine, dimethylglucosamine, ethylglucosamine, lysine, dicyclohexylamine, 1,6-hexanediamine, ethanolamine, glucosamine, meglumine, sarcosine, serine, trihydroxymethylaminomethane, aminopropylene glycol, 1-amino-2,3,4-butanetriol. As an example, the pharmaceutically acceptable salts include salts formed by the -COOH group with the following substances: sodium ion, potassium ion, calcium ion, magnesium ion, N-methylglucosamine, dimethylglucosamine, ethylglucosamine, lysine, dicyclohexylamine, 1,6-hexanediamine, ethanolamine, glucosamine, meglumine, sarcosine, serine, trihydroxymethylaminomethane, aminopropylene glycol, and 1-amino-2,3,4-butanetriol.

[0108] In addition, the basic nitrogen-containing group can be quaternized with the following reagents: lower alkyl halides, such as methyl, ethyl, propyl, and butyl chlorides, bromides, and iodides; dialkyl sulfates, such as dimethyl sulfate, diethyl sulfate, dibutyl sulfate, and dipentyl sulfate; long-chain halides, such as decyl, lauryl, myristyl, and stearyl chlorides, bromides, and iodides; aralkyl halides such as benzyl and phenethyl bromides, etc. As examples, pharmaceutically acceptable salts include hydrochlorides, sulfates, nitrates, hydrogen sulfates, hydrobromic acid salts, acetates, oxalates, citrates, methanesulfonates, formates, or meglumine salts, etc. Since the compounds of the present invention can have multiple salting sites, the pharmaceutically acceptable salts include not only salts formed at one salting site of the compounds of the present invention, but also salts formed at two, three, or all of the salting sites. Therefore, the molar ratio of the pharmaceutically acceptable salt of formula (I) compound to the anion of the acid or the cation of the base required for salt formation can vary over a wide range, for example, it can be 4:1 to 1:4, such as 3:1, 2:1, 1:1, 1:2, 1:3, etc.

[0109] In the conventional sense, the term "solvate" in this invention refers to a complex formed by a combination of a solute (such as an active compound or a salt of an active compound) and a solvent (such as water). The solvent refers to a solvent known or readily identifiable to those skilled in the art. If it is water, the solvate is generally referred to as a hydrate, such as a hemihydrate, monohydrate, dihydrate, trihydrate, or a substitute thereof. Detailed Implementation

[0110] The technical solution of the present invention will be further described in detail below with reference to specific embodiments. It should be understood that the following embodiments are merely illustrative and explanatory of the present invention, and should not be construed as limiting the scope of protection of the present invention. All technologies implemented based on the above content of the present invention are covered within the scope of protection intended by the present invention.

[0111] Unless otherwise stated, the raw materials and reagents used in the following examples are commercially available products or can be prepared by known methods.

[0112] Example 1: Preparation of the compound

[0113] Synthesis of compound A-001

[0114] first step:

[0115]

[0116] 2.0 g of compound A01-1 was placed in a 100 mL three-necked flask, and 20.0 mL of ultra-dry tetrahydrofuran was added. The mixture was cooled to 0 °C, and 5.0 mL of isopropyl magnesium chloride solution was added dropwise over 20 min. The mixture was stirred at 0 °C for 1 h, followed by the addition of 1.8 mL of trimethyl borate over 10 min. The mixture was stirred at 0 °C for 30 min and then brought to room temperature. The reaction was monitored by TLC until complete. 17 mL of 1 M hydrochloric acid was added, followed by extraction with water and ethyl acetate. The mixture was washed with saturated brine, and the organic layers were combined. The mixture was concentrated, filtered, and the filter cake was washed with n-hexane. After drying, 1.5 g of compound A01-2 was obtained as a white solid. Characterization data of compound A01-2: 1 ¹H NMR (500MHz, deuterated dimethyl sulfoxide) δ 8.43 (s, 2H), 7.35 (d, J = 1.2Hz, 1H), 7.10 (d, J = 1.3Hz, 1H).

[0117] Step Two:

[0118]

[0119] 1.0 g of compound A01-2 was placed in a 50 mL round-bottom flask, and 10.0 mL of diethyl ether was added. 1.0 g of pinacol was then added with stirring, and the reaction was carried out at room temperature. After the reaction was complete as detected by TLC, ethyl acetate was added for dilution. The organic phase was washed three times with water and once with saturated brine. The organic phase was concentrated and separated by column chromatography to obtain 1.3 g of A01-3 as a white solid. 1 ¹H NMR (500MHz, deuterated chloroform) δ 7.24 (d, J = 1.2Hz, 1H), 7.03 (d, J = 1.3Hz, 1H), 1.35 (s, 12H).

[0120] Step 3:

[0121]

[0122] 1.0 g of compound A01-3, 1.1 g of pinacol phenylboronic acid, 86.0 mg of DPPF palladium dichloride, and 1.5 g of anhydrous potassium phosphate were added to a 50 mL Shrek flask. Then, under nitrogen protection, 10.0 mL of tetrahydrofuran and 273.0 μL of water were added, and the reaction was carried out at room temperature. After the reaction was complete as detected by TLC, ethyl acetate was added for dilution. The organic phase was washed three times with water and once with saturated brine. The organic phase was concentrated and separated by column chromatography to obtain A-001 as a white solid, 531.0 mg.

[0123] Synthesis of compound A-013

[0124] first step:

[0125]

[0126] 2.0 g of compound A13-1 was placed in a 100 mL three-necked flask, and 20.0 mL of ultra-dry tetrahydrofuran was added. The mixture was cooled to 0 °C, and 5.0 mL of isopropyl magnesium chloride solution was added dropwise over 20 min. The mixture was stirred at 0 °C for 1 h, followed by the addition of 1.8 mL of trimethyl borate over 10 min. The mixture was stirred at 0 °C for 30 min, and then brought to room temperature. The reaction was monitored by TLC until complete. 17 mL of 1 M hydrochloric acid was added, followed by extraction with water and ethyl acetate. The mixture was washed with saturated brine, and the organic layers were combined. The mixture was concentrated, filtered, and the filter cake was washed with n-hexane. After drying, 1.5 g of compound A13-2 was obtained as a white solid. Characterization data of compound A13-2: 1 ¹H NMR (500MHz, deuterated dimethyl sulfoxide) δ 8.43 (s, 2H), 7.35 (d, J = 1.2Hz, 1H), 7.10 (d, J = 1.3Hz, 1H).

[0127] Step Two:

[0128]

[0129] 1.0 g of compound A13-2 was placed in a 50 mL round-bottom flask, and 20.0 mL of toluene was added. 782.0 mg of methyliminodiacetic acid was added with stirring, and the reaction was carried out at reflux. After the reaction was complete as detected by TLC, the mixture was diluted with water, filtered, the filter cake was washed with diethyl ether, and dried to obtain 1.2 g of A13-3 as a white solid. Characterization data of compound A13-3: 1 ¹H NMR (500MHz, deuterated dimethyl sulfoxide) δ 7.25 (d, J = 3.6 Hz, 1H), 7.07 (d, J = 3.6 Hz, 1H), 4.35 (d, J = 17.2 Hz, 2H), 4.14 (d, J = 17.2 Hz, 2H), 2.64 (s, 3H).

[0130] Step 3:

[0131]

[0132] 1.0 g of compound A13-3, 1.0 g of pinacol 4-hydroxyphenylboronic acid, 90.0 mg of DPPF palladium dichloride, and 1.7 g of anhydrous potassium phosphate were added to a 50 mL Shrek flask. Then, under nitrogen protection, 10.0 mL of tetrahydrofuran and 280.0 μL of water were added, and the reaction was carried out at room temperature. After the reaction was complete as detected by TLC, ethyl acetate was added for dilution. The organic phase was washed three times with water and once with saturated brine. The organic phase was concentrated and separated by column chromatography to obtain A-013 as a yellow solid, 248.0 mg.

[0133] Referring to the preparation methods for the synthesis of compounds A-001 or A-013 mentioned above, the compounds shown in Table 1 below were prepared by replacing the raw materials.

[0134] Table 1 shows the structural formulas of compound A.

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] Note: In Table 1, when R1 and R2 are selected from... When the groups are equal, N in the above groups coordinates with B.

[0144] Table 2 shows the mass spectrometry data and / or data of the compounds listed in Table 1. 1 H-NMR data. Unless otherwise specified, deuterated chloroform (CDCl3), deuterated methanol (CD3OD-d4), deuterated dimethyl sulfoxide (DMSO-d6), or heavy water (D2O) are used as test solvents.

[0145] In Table 2 and throughout the description below, “NMR” refers to nuclear magnetic resonance spectroscopy, and MS represents mass spectrometry. The following abbreviations are used: s = singlet, br = broad peak, d = doublet, dd = doubletuplet, t = triplet, td = tripletuplet, q = quartet, m = multipletuplet.

[0146] Table 2. Compound structure characterization data

[0147]

[0148]

[0149]

[0150]

[0151] Note: “—” in Table 2 indicates that NMR data for this compound were not tested.

[0152] Example 2 Biological Experiment

[0153] Given that *Pyrrosia lingua* infects plants via appressorium-mediated infection and can be cultured artificially indoors, *Pyrrosia lingua* can be used as a model pathogen to test the inhibitory effects of the compounds of this invention on conidium germination and appressorium formation. The relevant activities of the compounds of this invention are illustrated by the following examples.

[0154] Biological Experiment 1: Inhibitory Effect of Thiophene Borate Compounds on Conidial Germination and Appressorium Formation of *Pyrrosia lingua*

[0155] 1. Experimental material: P131 strain of *Pyrrosia lingua*.

[0156] 2. Experimental Method: The *Pyrrosia lingua* strain P131 was inoculated onto tomato-oat agar plates (OTA) and incubated at 28°C. After 3-5 days, the *Pyrrosia lingua* colonies on the OTA were completely broken up and then evenly spread onto new OTA plates and incubated at 28°C. When new mycelia appeared (usually 1-2 days), the mycelia were broken up with cotton swabs, rinsed with sterile water, and dried. The petri dishes were covered with a single layer of gauze and incubated at 28°C for 48 hours, resulting in the production of a large number of conidia on the OTA surface. The culture on the OTA was washed off with sterile water, filtered through three layers of lens paper, and the filtrate was the conidia solution. The conidia concentration was adjusted to 2 × 10⁻⁶. 5 Add the sample solution of the target compound to the sample solution at a concentration of 6.25 ppm or 1.56 ppm, and spot the solutions sequentially onto hydrophobic glass slides. Nine spots are spotted on each slide, and the slides are then treated in the dark and kept moist. After 12 hours, the solutions are observed and counted under a microscope.

[0157] 3. Statistical Analysis: Three inoculation sites were counted on each hydrophobic slide. At each inoculation site, the number of germinating conidia and appressorium formations from 100 conidia at its center were counted. The average of the three sets of data was calculated to obtain the conidia germination rate and appressorium formation rate. The conidia germination rate and appressorium formation rate obtained from parallel experiments using solvent were used as controls to calculate the inhibitory effect of the test compounds on conidia germination and appressorium formation. Table 3 shows the data from biological experiment 1 for the compounds of this invention, where "-" indicates no inhibitory effect at a concentration of 6.25 ppm, "+" indicates an inhibition rate of less than or equal to 50% at a concentration of 6.25 ppm, "++" indicates an inhibition rate of more than 50% at a concentration of 6.25 ppm, and "+++" indicates an inhibition rate of more than 50% at a concentration of 1.56 ppm. The experimental results show that the compounds of this invention have a good inhibitory effect on conidia germination and appressorium formation of *Pyrrosia lingua*, and some compounds exhibit excellent inhibitory activity.

[0158] Table 3. Inhibitory effects of the compounds of the present invention on conidial germination and appressorium formation of *Pyrrosia lingua*.

[0159]

[0160]

[0161] Biological Experiment 2: Control Effects of Thiophene Borate Compounds on Potted Rice Infected by Pyrethrum orientalis

[0162] 1. Experimental materials: Pyridae oryzae strain 16-117, rice varieties CO39 and Xiangwanxian 11.

[0163] 2. Experimental Methods: Sporulation and spore preparation were the same as in Biological Experiment 1. The conidial concentration was adjusted to 5 × 10⁻⁶. 4 Add the test compound stock solution to the solution at a concentration of 1 / mL to prepare a 100 ppm working solution. Spray 15 mL of the working solution onto susceptible rice varieties Xiangwanxian 11 and CO39, spraying 10 seedlings of 2-3 weeks old for each treatment. Incubate in the dark under moist conditions for 48 hours, then proceed with normal culture. Seven days after inoculation, evaluate the control efficacy of the test compound against rice blast.

[0164] 3. Statistics and Analysis: Table 4 shows the data of biological experiment 2 of the compounds of the present invention (average values ​​of each treatment). Rice blast leaf blast disease surveys were conducted in accordance with the agricultural industry standard "Technical Regulations for Field Monitoring of Rice Blast Resistance" (NY / T3685-2020). Specific standards are as follows: Grade 0: No disease on the entire leaf; Grade 1: Small brown necrotic spots on the leaf; Grade 2: Larger brown necrotic spots (1mm-2mm in diameter) on the leaf, but no typical lesions; Grade 3: Typical rice blast lesions, lesion area <2%; Grade 4: Typical rice blast lesions, 2% ≤ lesion area <5%; Grade 5: Typical rice blast lesions, 5% ≤ lesion area <10%; Grade 6: Typical rice blast lesions, 10% ≤ lesion area <25%; Grade 7: Typical rice blast lesions, 25% ≤ lesion area <50%; Grade 8: Typical rice blast lesions, 50% ≤ lesion area <75%; Grade 9: Typical rice blast lesions, lesion area ≥75%. Experimental results show that the compounds of this invention have good control effects on potted rice infected with *Pyrhodotorula oryzae*, and some compounds show excellent control effects.

[0165] Table 4. Control effects of the compounds of this invention on potted rice infected with *Pyrrosia lingua*.

[0166] Compound numbering Disease level A-001 3 A-011 2 A-012 1 A-013 1 A-016 0 A-021 1 A-023 0 A-024 1 A-026 0 A-032 2 A-034 0 A-036 1 A-037 1 A-038 0 A-040 2 A-042 2

[0167] Biological Experiment 3: The Control Effect of Thiophene Borate Compounds on Anthracnose Infection of Exvial Mango Leaves

[0168] 1. Experimental materials: Mango anthracnose strain SC2-1 and newly green 'Guifei' mango tender leaves were placed in an inoculation box for later use.

[0169] 2. Experimental Method: The anthrax strain SC2-1 was inoculated onto tomato-oat agar plates (OTA) and incubated at 25°C under constant temperature and light. After 5-7 days, the mycelia on the OTA were gently broken with a cotton swab, rinsed with sterile water, and air-dried. The petri dish was covered with a single layer of gauze and incubated at 25°C under light for 3-5 days, resulting in the production of a large number of spores on the OTA surface. The culture on the OTA was washed off with sterile water, filtered through three layers of lens paper, and the filtrate was the spore solution. The spore concentration was adjusted to 1×10⁻⁶. 6 Add the test compound stock solution to the solution at a concentration of 10 μL / mL to prepare working solutions of 200 ppm, 100 ppm, or 50 ppm. Spot 10 μL of the working solution onto the surface of mango leaves, treat in the dark for 24 h, and then incubate normally. Evaluate the control effect of the test compound 7 days after inoculation.

[0170] 3. Statistics and Analysis: Five leaves were counted for each treatment, and one inoculation point was counted for each leaf. The lesion area at each inoculation point was counted, and the average value was calculated to obtain the lesion area. The lesion area obtained from parallel experiments using solvent was used as a control to calculate the inhibitory effect of the test compounds on anthracnose-infected mango leaves. Table 5 shows the data from biological experiment 3 for the compounds of this invention. "+" indicates an inhibition effect of less than 40% at 200 ppm, "++" indicates an inhibition effect of more than 40% at 100 ppm, and "+++" indicates an inhibition effect of more than 80% at 50 ppm. The experimental results show that the compounds of this invention have good control effects against anthracnose-infected detached mango leaves, and some compounds show excellent control effects.

[0171] Table 5. The preventive and therapeutic effects of the compounds of this invention on anthrax-infected detached mango leaves.

[0172]

[0173]

[0174] Biological Experiment 4: The Control Effect of Thiophene Borate Compounds on Fusarium Head Blight Infection in Potted Wheat

[0175] 1. Experimental materials: Fusarium graminearum strain Fg0609 and "Fielder" wheat cultured to the pre-ear and grain flowering stage.

[0176] 2. Experimental Method: The *Fusarium graminearum* mycelium cake grown on PDA medium for 5 days was placed in CMC liquid medium and incubated at 28℃ and 180 rpm for 7 days. The mixture was filtered through three layers of lens paper, and the filtrate was used as the spore solution. The spore solution concentration was adjusted to 1×10⁻⁶. 5Add the stock solution of the test compound to the solution at a concentration of 10 μL / mL to prepare a 100 ppm working solution. Use a pipette to inject 10 μL of the working solution into wheat ears before flowering, five ears per treatment. Afterward, keep the solution moist for 2 days and then incubate normally. Evaluate the control effect of the test compound 14 days after inoculation.

[0177] 3. Statistics and Analysis: Table 6 shows the data from biological experiment 4 of the compounds of this invention (average values ​​for each treatment). A survey of wheat scab disease was conducted according to the agricultural industry standard "Technical Regulations for Identification of Resistance to Fusarium Head Blight in Regional Trials of Wheat" (NY / T2954-2016), with the following specific standards: Grade 0: No visible symptoms on inoculated spikelets; Grade 1: Disease only on inoculated spikelets; or disease on individual adjacent spikelets, but the lesions do not extend to the rachis; Grade 2: Disease on the rachis, with diseased spikelets accounting for less than 1 / 4 of the total spikelets; Grade 3: Disease on the rachis, with diseased spikelets accounting for 1 / 4-1 / 2 of the total spikelets; Grade 4: Disease on the rachis, with diseased spikelets accounting for more than 1 / 2 of the total spikelets. The experimental results show that the compounds of this invention have good control effects against Fusarium head blight infection in potted wheat, and some compounds exhibit excellent control effects.

[0178] Table 6. Control effects of the compounds of this invention on potted wheat infected with Fusarium graminearum.

[0179] Compound numbering Disease level A-006 3 A-011 2 A-012 1 A-013 1 A-016 0 A-020 2 A-026 1 A-032 2 A-034 0 A-036 1 A-040 2 A-042 1

[0180] Biological Experiment 5: The Control Effect of Thiophene Borate Compounds on Phytophthora Infection of Potted Potatoes

[0181] 1. Experimental materials: The seedlings of the pathogenic Phytophthora blight medium-strong strain "MZ" and the potato late blight susceptible variety "Desiree" were cultured normally for 2 weeks and then placed in an inoculation box for use.

[0182] 2. Experimental Method: The sporangia were cultured on PDA medium. After sporangia were produced, they were washed off with sterile water, filtered through double-layered gauze to prepare a sporangia suspension, and incubated at 4℃ in the dark for 3 hours. The prepared sporangia solution was then adjusted with sterile water at 4℃ to a concentration of 4×10⁻⁶. 3 A suspension of sporangia / mL was prepared. The stock solution of the test compound was diluted with water to a working concentration of 100 ppm. Before inoculation, the plants to be treated were placed in an artificial climate greenhouse at 20℃ for acclimatization 4 hours in advance. After acclimatization, the working solution was sprayed evenly on both sides of the leaves of the treated plants. Five plants were treated per treatment, and each plant was sprayed with 60 mL. After the working solution was allowed to air dry naturally, the plants were cultured normally for 24 hours. Then, the plants were sprayed with the prepared sporangia suspension for inoculation. After 24 hours of dark treatment, the plants were cultured under normal light (20℃, 18 hours light / 6 hours dark). The disease situation was observed at any time. The control effect of the test compound on potato late blight was evaluated after 7 days.

[0183] 3. Statistics and Analysis: Table 7 shows the data from biological experiment 5 of the compounds of this invention (average values ​​for each treatment). A survey of potato late blight disease was conducted according to the agricultural industry standard "Technical Specification for Indoor Identification of Potato Resistance to Late Blight" (NY / T3063-2016). The specific standards are as follows: Grade 0: No symptoms on inoculated leaves; Grade 1: Only pinhead-sized necrotic spots appear on the leaves; Grade 2: Lesion diameter less than 0.5 cm, without a surrounding chlorotic halo; Grade 3: Lesion diameter 0.5 cm-1 cm, water-soaked lesions with a surrounding chlorotic halo, white mycelium visible on the lesion surface; Grade 4: Lesions continue to expand, occupying 1 / 2 of the total leaf area, with a distinct chlorotic halo around the lesion and a distinct white mold layer; Grade 5: Lesions occupy more than 2 / 3 of the leaf area, with a large amount of white mold on the lesion surface and tissue necrosis. The experimental results show that the compounds of this invention have good control effects against Phytophthora infestation in potted potatoes, and some compounds show excellent control effects.

[0184] Table 7. Control effects of the compounds of this invention on potted potatoes infected with pathogenic Phytophthora.

[0185] Compound numbering Disease level A-009 2 A-011 2 A-012 1 A-013 1 A-016 0 A-021 1 A-032 2 A-034 0 A-036 1 A-038 1 A-043 1

[0186] Biological Experiment 6: The Control Effect of Thiophene Borate Compounds on Potted Peppers Infected by Phytophthora capsici

[0187] 1. Experimental materials: The *Phytophthora capsici* strain BYA5 and *Horn Pepper* seedlings were cultured normally for 2 weeks and then placed in an inoculation box for later use.

[0188] 2. Experimental Methods: The strain was cultured on PDA medium for 10 days, then soaked in a small amount of sterile water and placed at 4°C in the dark for 3 hours before storage. The prepared sporangia solution was adjusted with sterile water at 4°C to a concentration of 1×10⁻⁶. 5 A suspension of spores / mL was prepared. The stock solution of the test compound was diluted with water to a working concentration of 100 ppm. Five plants were treated per treatment, and each plant was sprayed with 20 mL of the working solution of the compound. After air drying, the plants were inoculated by drenching the roots with 10 mL of the prepared spore suspension. After 24 hours of dark treatment, the plants were cultured under normal light (20℃, 18 hours light / 6 hours dark), and the disease development was observed at any time. The control effect of the test compound on pepper blight was evaluated after 5-7 days.

[0189] 3. Statistics and Analysis: Table 8 shows the data from biological experiment 6 of the compounds of this invention (average values ​​for each treatment). A survey of pepper blight disease was conducted according to the agricultural industry standard "Technical Specification for Identification of Pepper Disease Resistance Part 1: Technical Specification for Identification of Pepper Blight Disease" (NY / T2060.1-2011). The specific standards are as follows: Grade 0: No symptoms; Grade 1: Slight blackening of the seedling rootstock, leaves do not wilt or wilt recoverably; Grade 2: Blackening of the seedling rootstock up to 1-2 cm, irreversible wilting of leaves, occasional shedding of lower leaves; Grade 3: Blackening of the seedling rootstock exceeding 2 cm, obvious wilting of leaves or obvious leaf drop; Grade 4: Blackening and constriction of the seedling rootstock, all leaves except the growing point fall off or the plant wilts; Grade 5: Plant dies. The experimental results show that the compounds of this invention have good control effects on potted peppers infected with Phytophthora capsici, and some compounds show excellent control effects.

[0190] Table 8. Control effects of the compounds of this invention on potted pepper plants infected with Phytophthora capsici.

[0191]

[0192]

[0193] The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiments. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. Thiophene borate esters of formula (I), their stereoisomers, racemates, tautomers, isotopic labels, nitrogen oxides, agriculturally acceptable salts or esters, solvates, or solvates of agriculturally acceptable salts: in, This indicates that R1 and R2, together with the two O atoms attached to them and B, constitute an unsubstituted compound, or are optionally substituted by one, two or more R atoms. a The following groups are substituted: 5-12 membered heterocyclic groups or benzo5-12 membered heterocyclic groups; The R a Selected from H, =O, C 1-12 Alkyl or halogenated C 1-12 alkyl; R3 is selected from: H, R4 is selected from: H, R5 is selected from: H, m is a natural number selected from 0 to 5; R b They may be the same or different, and are independently selected from H, halogen, C1-6 alkyl, C1-6 alkoxy, cyano, hydroxyl, C1-6 alkyl ester, aldehyde, 5-10 heteroaryl, -OC 6-10 Aryl; the C1-6 alkyl, C1-6 alkoxy, and C1-6 alkyl ester groups are unsubstituted or optionally substituted with one, two, or more halogens; The 5-10 quinone heteroaryl group, -OC 6-10 The aryl group is unsubstituted, or optionally substituted with one, two or more halogens or C1-6 alkyl groups; R3, R4, and R5 are not all H at the same time.

2. The compound according to claim 1, characterized in that, This indicates that R1 and R2, together with the two O atoms attached to them and B, constitute an unsubstituted compound, or are optionally substituted by one, two or more R atoms. a The following groups are substituted: 5-10 membered heterocyclic groups or benzo5-10 membered heterocyclic groups; Preferably, This indicates that R1 and R2, together with the two O atoms attached to them and B, form the following groups: m is a natural number between 0 and 4; * indicates the linking site of a group; Preferably, This indicates that R1 and R2, together with the two O atoms attached to them and B, form the following groups: Preferably, R a They may be the same or different, and are independently selected from H, =O, C1-6 alkyl, and halogenated C1-6 alkyl.

3. The compound according to claim 1 or 2, characterized in that, R3 is selected from: H, m is a natural number selected from 0 to 5; R b They may be the same or different, and are independently selected from H, halogen, C1-6 alkyl, C1-6 alkoxy, cyano, hydroxyl, C1-6 alkyl ester, aldehyde, 5-10 heteroaryl, -OC 6-10 Aryl; The C1-6 alkyl, C1-6 alkoxy, and C1-6 alkyl ester groups are unsubstituted or optionally substituted with one, two, or more halogens; The 5-10 quinone heteroaryl group, -OC 6-10 The aryl group is unsubstituted, or optionally substituted with one, two or more halogens or C1-6 alkyl groups; Preferably, the 5-10 member heteroaryl group is selected from: piperidinyl, piperazineyl; Preferably, -OC 6-10 The aryl group is selected from: -O-phenyl, -O-naphthyl; Preferably, R3 is selected from H, 4. The compound according to any one of claims 1-3, characterized in that, R4 is selected from: H, m is a natural number selected from 0 to 5; R b They may be the same or different, and are independently selected from H, halogen, C1-6 alkyl, C1-6 alkoxy, cyano, and hydroxyl. The C1-6 alkyl and C1-6 alkoxy groups are unsubstituted or optionally substituted with one, two or more halogens; Preferably, R b They may be the same or different, and are independently selected from H, halogen, C1-4 alkyl, C1-4 alkoxy, cyano, and hydroxyl; the C1-4 alkyl and C1-4 alkoxy are unsubstituted or optionally substituted by one, two, or more halogens.

5. The compound according to any one of claims 1-4, characterized in that, R5 is selected from: H, m is a natural number selected from 0 to 5; R b They may be the same or different, and are independently selected from H, halogen, C1-6 alkyl, C1-6 alkoxy, cyano, and hydroxyl. The C1-6 alkyl and C1-6 alkoxy groups are unsubstituted or optionally substituted with one, two or more halogens; Preferably, R b They may be the same or different, and are independently selected from H, halogen, C1-4 alkyl, C1-4 alkoxy, cyano, and hydroxyl; the C1-4 alkyl and C1-4 alkoxy are unsubstituted or optionally substituted by one, two, or more halogens.

6. The compound according to any one of claims 1-5, characterized in that, The compound is selected from the compounds shown in formula (I-1): in, R3 has the definition as described in any one of claims 1-5; Alternatively, the compound may be selected from compounds represented by formula (I-2): in, R4 has the definition as described in any one of claims 1-5; Alternatively, the compound may be selected from compounds represented by formula (I-3): in, R5 has the definition as described in any one of claims 1-5.

7. The compound according to any one of claims 1-6, characterized in that, The compound is selected from the following compounds:

8. A pesticide composition comprising the compound of any one of claims 1-7, its stereoisomer, racemate, tautomer, isotope label, nitrogen oxide, agriculturally acceptable salt or ester, solvate, or a solvate of an agriculturally acceptable salt.

9. The use of the compound of any one of claims 1-7, its stereoisomer, racemate, tautomer, isotope label, nitrogen oxide, agriculturally acceptable salt or ester, solvate or solvate of an agriculturally acceptable salt, or the composition of claim 8 in the preparation of a fungicide.

10. Use of the compound of any one of claims 1-7, its stereoisomers, racemates, tautomers, isotopic markers, nitrogen oxides, agriculturally acceptable salts or esters, solvates or solvates of agriculturally acceptable salts, or the composition of claim 8, for the prevention and control of plant diseases caused by fungi and / or oomycetes.

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