Pyridine amine compound as well as preparation method and application thereof

Abstract

The invention provides a compound shown in a formula (I) or a pharmaceutically acceptable salt thereof and application of the compound in preparation of bactericides in the agricultural field or the horticultural field, # imgabs0, the compound shown in the formula (I) shows excellent biological activity on various germs in the agricultural field or the horticultural field, and an excellent effect can be obtained at a low dosage.

Description

Technical Field

[0001] The present invention belongs to the technical field of agricultural or horticultural fungicides, and particularly relates to a pyridineamine compound, a preparation method thereof, and uses thereof. Background Art

[0002] In the agricultural field, with the popularization of straw returning to the field and no-tillage techniques, the treatment of plant residues in production is insufficient, and many pathogens overwinter and oversummer through plants, resulting in a large amount of plant pathogens remaining in the soil. In addition, with the increasingly serious problem of disease resistance, farmers need to increase the dosage of pesticides, but this will increase drug residues and cause pollution and burden to the environment. Therefore, new pesticide varieties with high effectiveness need to be developed. Summary of the Invention

[0003] To solve the above technical problems, the present invention provides a pyridineamine compound represented by the following formula (I) or a pharmaceutically acceptable salt thereof,

[0004]

[0005] wherein R1 is the same or different and is independently selected from hydrogen, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 haloalkyl, C1-C 10 haloalkoxy, halogen, hydroxyl, amino, nitro, cyano;

[0006] R2 is the same or different and is independently selected from hydrogen, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 haloalkyl, C1-C 10 haloalkoxy, halogen, hydroxyl, amino, nitro, cyano;

[0007] R a 、R b is the same or different and is independently selected from hydrogen, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 haloalkyl, C1-C 10 haloalkoxy, halogen, hydroxyl, amino, nitro, cyano;

[0008] Y is selected from -O-, -S-, -Se-, -CH2-, -CH2O-, -OCH2-, -CH2S-, -SCH2-;

[0009] Q is selected from optionally substituted by one, two or more R s1Substituted C6-20 aryl, 5-20 membered heteroaryl, 3-20 membered cycloalkyl, 3-20 membered heterocycloalkyl,

[0010] R s1 which are the same or different and are independently selected from each other from the following groups: hydrogen, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 haloalkyl, C1-C 10 haloalkoxy, halogen, hydroxy, amino, nitro, cyano;

[0011] p is an integer and is selected from 0, 1, 2, 3;

[0012] q is an integer and is selected from 0, 1, 2, 3, 4;

[0013] represents the attachment site of the group.

[0014] According to an embodiment of the present invention, provided that the compound represented by formula (I) does not include the following compounds:

[0015]

[0016] According to an embodiment of the present invention, R1 are the same or different and are independently selected from each other from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; preferably, R1 are the same or different and are independently selected from each other from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; more preferably, R1 are the same or different and are independently selected from each other from hydrogen, C1-C4 alkyl, halogen; exemplarily, R1 are the same or different and are independently selected from each other from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, fluorine, chlorine, bromine, iodine.

[0017] According to an embodiment of the present invention, p is an integer selected from 0, 1. According to an embodiment of the present invention, R1 is selected from hydrogen, methyl.

[0018] According to an embodiment of the present invention, R2s are the same or different and independently selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; preferably, the R2s are the same or different and independently selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; more preferably, the R2s are the same or different and independently selected from hydrogen, halogen; exemplarily, the R2s are the same or different and independently selected from hydrogen, fluorine, chlorine, bromine, iodine.

[0019] According to an embodiment of the present invention, q is an integer selected from 0. According to an embodiment of the present invention, R2 is selected from hydrogen.

[0020] According to an embodiment of the present invention, R a 、R b are the same or different and independently selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; preferably, R a 、R b are the same or different and independently selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; more preferably, R a 、R b are the same or different and independently selected from hydrogen, halogen; exemplarily, R a 、R b are the same or different and independently selected from hydrogen, fluorine, chlorine, bromine, iodine. According to an embodiment of the present invention, R a 、R b are both selected from hydrogen.

[0021] According to an embodiment of the present invention, Y is selected from -O-, -S-, -CH2O-, -OCH2-, -CH2S-, -SCH2-; preferably, Y is selected from -O-, -CH2O- or -OCH2-.

[0022] According to an embodiment of the present invention, Q is selected from a C6-16 aryl, 5-16 membered heteroaryl, 3-16 membered cycloalkyl, 3-16 membered heterocycloalkyl optionally substituted by one, two or more R s1 ; preferably, Q is selected from a C6-10 aryl, 5-10 membered heteroaryl, 3-10 membered cycloalkyl, 3-10 membered heterocycloalkyl optionally substituted by one, two or more R ; more preferably, Q is selected from a C6-10 aryl, 5-10 membered heteroaryl, 3-10 membered cycloalkyl, 3-10 membered heterocycloalkyl optionally substituted by one, two or more R s1 ; more preferably, Q is selected from a C6-10 aryl, 5-10 membered heteroaryl, 3-10 membered cycloalkyl, 3-10 membered heterocycloalkyl optionally substituted by one, two or more Rs1 Substituted C6-10 aryl, 5-10 membered heteroaryl, 3-6 membered cycloalkyl, 3-6 membered heterocycloalkyl,

[0023] According to an embodiment of the present invention, the C6-10 aryl is selected from phenyl and naphthyl.

[0024] According to an embodiment of the present invention, the heteroaryl and heterocyclic group contain at least one heteroatom selected from N, O, and S.

[0025] According to an embodiment of the present invention, the 5-10 membered heteroaryl and 3-6 membered heterocycloalkyl contain at least one (such as one, two, three, four, etc.) heteroatom selected from N, O, and S; preferably, the 5-10 membered heteroaryl and 3-6 membered heterocycloalkyl contain one, two, or three N atoms; for example, pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazolinyl, triazinyl, etc.

[0026] According to an embodiment of the present invention, Q is selected from phenyl, naphthyl, pyrrolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazolinyl, triazinyl optionally substituted by one, two, or more R s1 or

[0027] According to an embodiment of the present invention, R s1 are the same or different and independently selected from each other from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; preferably, R s1 are the same or different and independently selected from each other from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; more preferably, R s1 are the same or different and independently selected from each other from hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl; exemplarily, R s1 are the same or different and independently selected from each other from hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl, and methyl.

[0028] According to an embodiment of the present invention, Q is selected from

[0029]

[0030] R s1 having the foregoing definitions;

[0031] n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7.

[0032] According to an embodiment of the present invention, Q is selected from

[0033]

[0034] According to an embodiment of the present invention, the compound represented by formula (I) is selected from the compounds represented by formula (II) below or a pharmaceutically acceptable salt thereof:

[0035]

[0036] Wherein, R1 is selected from hydrogen, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 haloalkyl, C1-C 10 haloalkoxy, halogen, hydroxyl, amino, nitro, cyano;

[0037] Y and Q have the foregoing definitions.

[0038] According to an embodiment of the present invention, R1 is selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, halogen, hydroxyl, amino, nitro, cyano; preferably, R1 is selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, hydroxyl, amino, nitro, cyano; more preferably, R1 is selected from hydrogen, C1-C4 alkyl, halogen; exemplarily, R1 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, butyl, fluorine, chlorine, bromine, iodine. According to an embodiment of the present invention, R1 is selected from hydrogen, methyl.

[0039] According to an embodiment of the present invention, the compound of formula (I) is selected from the following compounds or a pharmaceutically acceptable salt thereof,

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] For the purpose of reducing the length of the specification, the exemplary groups and / or compounds of the present invention are described in the form of the above table. The present invention also provides a method for preparing the compound of formula (I) or a pharmaceutically acceptable salt thereof as described above, and the preparation method includes: 1) reacting the compound shown in formula (VIII) with the compound shown in formula (IX) to obtain the compound shown in formula (VII);

[0047] 2) reacting the compound shown in formula (VII) to obtain the compound shown in formula (VI);

[0048] 3) reacting the compound shown in formula (VI) to obtain the compound shown in formula (V);

[0049] 4) reacting the compound shown in formula (V) with the compound shown in formula (IV) to obtain the compound shown in formula (III);

[0050] 5) reacting the compound shown in formula (III) to obtain the compound shown in formula (I);

[0051] The reaction formulas are shown as follows:

[0052]

[0053] Wherein, R1, R2, R a , R b , Y, Q, p, q have the definitions as described above;

[0054] L1 and L2 are selected from leaving groups, such as halogen atoms (exemplarily fluorine, chlorine, bromine or iodine). According to an embodiment of the present invention, the reaction route of the preparation method is as follows:

[0055]

[0056] Wherein, R1, Y, Q have the definitions as described above;

[0057] L1 and L2 are selected from leaving groups, such as halogen atoms (exemplarily fluorine, chlorine, bromine or iodine).

[0058] According to an embodiment of the present invention, in step 1), the compound shown in (VIII) and the compound shown in formula (IX) are reacted in the presence of a base to prepare the compound (VII). Preferably, the base is selected from organic bases and inorganic bases; for example, selected from one, two or more of triethylamine, pyridine, DIEA, DMAP, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, potassium tert-butoxide, sodium hydride, etc. Preferably, the reaction is carried out in a solvent; the solvent can be selected from one, two or more of N,N-dimethylformamide, toluene, butanone, acetonitrile, tetrahydrofuran, etc. Preferably, the reaction temperature is 25°C to 150°C.

[0059] According to an embodiment of the present invention, in step 2), compound (VII) is used to prepare compound (VI) in the presence of a reducing agent (such as lithium aluminum hydride or diisobutylaluminum hydride). Preferably, the reaction is carried out in a solvent; the solvent can be selected from one, two or more of benzene, toluene, tetrahydrofuran, methyltetrahydrofuran, diethyl ether, etc. Preferably, the reaction temperature is -30°C to 25°C.

[0060] According to an embodiment of the present invention, in step 3), compound (VI) undergoes a halogenation reaction to prepare compound (V). Preferably, the halogenating agent can be selected from acyl halides of inorganic acids, such as thionyl chloride, phosphorus oxychloride, phosphorus tribromide, etc. Preferably, the halogenation reaction can be carried out with carbon tetrachloride or carbon tetrabromide in the presence of triphenylphosphine. Preferably, the halogenation reaction can be carried out without a solvent or in a solvent-free medium; preferably, the solvent can be selected from one, two or more of aromatic solvents, halogenated alkane solvents, alkane solvents, such as one, two or more of toluene, 1,2-dichloroethane or petroleum ether, etc. Preferably, the temperature of the halogenation reaction can be 15°C to 120°C.

[0061] According to an embodiment of the present invention, in step 4), compound (V) reacts with compound (IV) in the presence of a base to prepare compound (III). Preferably, the base is selected from organic bases and inorganic bases; for example, it can be selected from one, two or more of triethylamine, pyridine, DIEA, DMAP, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, potassium tert-butoxide, sodium hydride, etc. Preferably, the reaction can be carried out in the presence of a catalyst (such as Xphos, Pd(CH3CN)2Cl2) (which can promote the progress of the reaction). Preferably, the reaction is carried out in a solvent; the solvent can be selected from one, two or more of toluene, acetonitrile, tetrahydrofuran, etc. Preferably, the reaction temperature is 25°C to 120°C.

[0062] According to an embodiment of the present invention, in step 5), compound (III) undergoes deamination protection in the presence of an acid to prepare compound (I). Preferably, the acid is selected from organic acids and inorganic acids; for example, it can be selected from formic acid, trifluoroacetic acid, p-toluenesulfonic acid, etc. Preferably, the reaction temperature is 0°C to 80°C.

[0063] According to an embodiment of the present invention, the above reactions can be carried out with reference to the methods described in patent documents WO2022127782 or WO2015025019 or other similar methods.

[0064] The preparation method of the present invention can, according to the reaction conditions suitable for each case and the selection of raw materials, for example, replace only one substituent with another substituent according to the present invention in a one-step reaction, or replace multiple substituents with other substituents according to the present invention in the same reaction step.

[0065] If the respective compounds cannot be obtained via the above routes, they can be prepared by derivatizing other compounds of formula (I) or by making conventional variations to the said synthetic routes.

[0066] The reaction mixture is worked up in a conventional manner, such as by mixing with water, phase separation, and purifying the crude product by chromatography, for example, on alumina or silica gel.

[0067] According to an embodiment of the present invention, the pharmaceutically acceptable salts of the compounds of formula (I) can be prepared by known methods. For example, the pharmaceutically acceptable acid addition salts of the compounds of formula (I) are obtained by treatment with a suitable acid. The preparation method is as follows: reacting the compound of formula (I) with an acid (organic acid, inorganic acid, such as hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid, malic acid or citric acid, etc.), the pharmaceutically acceptable salts of the compounds of formula (I) can be obtained. Preferably, the reaction is carried out in a solvent; preferably, the solvent is selected from water, ether, toluene, etc.

[0068] The above preparation method can obtain a mixture of isomers of the compounds of formula (I). If pure isomers are required, they can be separated by conventional methods such as crystallization or chromatography.

[0069] Unless otherwise specified, all of the above reactions can be conveniently carried out at atmospheric pressure or the autogenous pressure of a particular reaction.

[0070] The present invention also provides the use of the compounds of formula (I) or their pharmaceutically acceptable salts in the preparation of fungicides, which are used in the agronomic field (agricultural fungicides) or the horticultural field (horticultural fungicides).

[0071] The present invention also provides the use of at least one of the compounds of formula (I) or their pharmaceutically acceptable salts as a fungicide, which is used in the agronomic field (agricultural fungicides) or the horticultural field (horticultural fungicides).

[0072] The present invention also provides a composition, which comprises at least one of the compounds of formula (I) or their pharmaceutically acceptable salts as an active ingredient.

[0073] The present invention also provides the use of the said composition as a fungicide, which can be used in the agronomic field (agricultural fungicides) or the horticultural field (horticultural fungicides).

[0074] The present invention also provides a method for controlling germs (such as phytopathogenic bacteria) or diseases in the field of agronomy or horticulture, said method comprising applying an effective amount of at least one of the compounds represented by the above formula (I), or a pharmaceutically acceptable salt thereof, or said composition, onto the growth medium of the germs or diseases (such as phytopathogens).

[0075] Examples of diseases mentioned below are only used to illustrate the present invention, but in no way limit the present invention.

[0076] The compound shown by formula (I), its pharmaceutically acceptable salt or the composition can be used for preventing and treating the following diseases or their corresponding pathogenic bacteria: oomycete diseases such as downy mildew (downy mildew of cucumber, downy mildew of rape, downy mildew of soybean, downy mildew of sugar beet, downy mildew of sugarcane, downy mildew of tobacco, downy mildew of pea, downy mildew of towel gourd, downy mildew of wax gourd, downy mildew of muskmelon, downy mildew of Chinese cabbage, downy mildew of spinach, downy mildew of radish, downy mildew of grape, downy mildew of onion), white rust (white rust of rape, white rust of Chinese cabbage), damping-off (damping-off of rape, damping-off of tobacco, damping-off of tomato, damping-off of pepper, damping-off of eggplant, damping-off of cucumber, damping-off of cotton seedling), cottony rot (cottony rot of pepper, cottony rot of towel gourd, cottony rot of wax gourd), phytophthora blight (phytophthora blight of broad bean, phytophthora blight of cucumber, phytophthora blight of pumpkin, phytophthora blight of wax gourd, phytophthora blight of watermelon, phytophthora blight of muskmelon, phytophthora blight of pepper, phytophthora blight of Chinese chives, phytophthora blight of garlic, phytophthora blight of cotton), late blight (late blight of potato, late blight of tomato), etc.;Deuteromycete diseases, such as fusarium wilt (sweet potato fusarium wilt, cotton fusarium wilt, sesame fusarium wilt, castor bean fusarium wilt, tomato fusarium wilt, kidney bean fusarium wilt, cucumber fusarium wilt, towel gourd fusarium wilt, pumpkin fusarium wilt, wax gourd fusarium wilt, watermelon fusarium wilt, melon fusarium wilt, pepper fusarium wilt, broad bean fusarium wilt, rape fusarium wilt, soybean fusarium wilt), root rot (pepper root rot, eggplant root rot, kidney bean root rot, cucumber root rot, balsam pear root rot, cotton black root rot, broad bean root rot), damping-off (cotton seedling damping-off, sesame damping-off, pepper damping-off, cucumber damping-off, Chinese cabbage damping-off), anthracnose (sorghum anthracnose, cotton anthracnose, kenaf anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, mulberry anthracnose, pepper anthracnose, eggplant anthracnose, kidney bean anthracnose, cucumber anthracnose, balsam pear anthracnose, zucchini anthracnose, wax gourd anthracnose, watermelon anthracnose, melon anthracnose, litchi anthracnose), verticillium wilt (cotton verticillium wilt, sunflower verticillium wilt, tomato verticillium wilt, pepper verticillium wilt, eggplant verticillium wilt), scab (zucchini scab, wax gourd scab, melon scab), gray mold (cotton boll gray mold, kenaf gray mold, tomato gray mold, pepper gray mold, kidney bean gray mold, celery gray mold, spinach gray mold, kiwifruit gray mold), brown spot (cotton brown spot, jute brown spot, sugar beet brown spot, peanut brown spot, pepper brown spot, wax gourd brown spot, soybean brown spot, sunflower brown spot, pea brown spot, broad bean brown spot), black spot (flax false black spot, rape black spot, sesame black spot, sunflower black spot, castor bean black spot, tomato black spot, pepper black spot, eggplant black spot, kidney bean black spot, cucumber black spot, celery black rot, carrot black rot, carrot black spot, apple black spot, peanut black spot), leaf spot (tomato leaf spot, pepper leaf spot, celery leaf spot), early blight (tomato early blight, pepper early blight, eggplant early blight, potato early blight, celery early blight), ring spot (soybean ring spot, sesame ring spot, kidney bean ring spot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon leaf blight, melon leaf blight), basal stem rot (tomato basal stem rot, kidney bean basal stem rot), and others (maize circular spot, kenaf stem break, rice blast, chestnut black sheath, sugarcane eyespot, cotton boll aspergillosis, peanut crown rot, soybean stem blight, soybean black dot, melon large spot, peanut net blotch, tea red leaf spot, pepper white spot, wax gourd leaf spot, celery black rot, spinach core rot, kenaf leaf mold, kenaf leaf spot, jute stem spot, soybean purple spot, sesame leaf spot, castor bean gray spot, tea brown leaf spot, eggplant brown round star spot, kidney bean red spot, balsam pear white spot, watermelon spot, jute dry rot, sunflower root and stem rot, kidney bean charcoal rot, soybean target spot, eggplant Corynespora leaf spot, cucumber target spot, tomato leaf mold, eggplant leaf mold, broad bean red spot, etc.);Basidiomycete diseases, such as rust diseases (wheat stripe rust, wheat stem rust, wheat leaf rust, peanut rust, sunflower rust, sugarcane rust, leek rust, onion rust, chestnut rust, soybean rust), smut diseases (maize head smut, maize smut, sorghum head smut, sorghum loose smut, sorghum covered smut, sorghum kernel smut, chestnut kernel smut, sugarcane smut, bean rust) and others (such as wheat sharp eyespot, rice sheath blight, etc.); Ascomycete diseases, such as powdery mildew diseases (wheat powdery mildew, rape powdery mildew, sesame powdery mildew, sunflower powdery mildew, sugar beet powdery mildew, eggplant powdery mildew, pea powdery mildew, towel gourd powdery mildew, pumpkin powdery mildew, zucchini powdery mildew, wax gourd powdery mildew, muskmelon powdery mildew, grape powdery mildew, broad bean powdery mildew), sclerotinia diseases (flax sclerotinia, rape sclerotinia, soybean sclerotinia, peanut sclerotinia, tobacco sclerotinia, pepper sclerotinia, eggplant sclerotinia, bean sclerotinia, pea sclerotinia, cucumber sclerotinia, balsam pear sclerotinia, wax gourd sclerotinia, watermelon sclerotinia, celery sclerotinia), scab diseases (apple scab, pear scab), etc.

[0077] According to an embodiment of the present invention, the compound of formula (I) or its agrochemically acceptable salt or the composition can be used to control the following pathogenic bacteria or their corresponding diseases:

[0078] Gram-negative bacteria: Erwinia (causing fire blight of pear, etc.); Pectobacterium (causing soft rot of cruciferous vegetables, blackleg of potato, etc.); Dickeya (causing stem rot of sweet potato, bacterial stalk rot of maize, bacterial foot rot of rice, blackleg of potato, rusty water disease of pear, etc.); Pantoea (causing bacterial wilt of maize, Pantoea leaf spot of maize, bacterial leaf blight of adzuki bean, canker pathogen of stone fruit tree, etc.); Pseudomonas (causing canker pathogen of peach tree, bacterial blight of pea, bacterial black spot of cruciferae, bacterial leaf spot of tomato, bacterial speck of tomato, bacterial black spot of rape, bacterial angular leaf spot of sesame, bacterial angular leaf spot of cucumber, wildfire of tobacco, bacterial brown spot of maize, bacterial brown spot of maize, bacterial stem blight of broad bean, bacterial leaf spot of soybean, bacterial leaf blight of sugar beet, bacterial pith necrosis of tomato, Pseudomonas aeruginosa soft rot of ginseng, etc.); Ralstonia (causing various bacterial wilt diseases, etc.); Burkholderia (causing bacterial wilt of carnation, onion rot, bacterial panicle blight of rice, etc.); Acidovorax (causing bacterial fruit blotch of cucurbit, brown spot of orchid, brown stripe of oat, bacterial leaf spot of konjac, etc.); Xanthomonas (causing bacterial leaf blight of rice, bacterial leaf streak of rice, spot disease of pepper and tomato, scab disease of pepper and tomato, bacterial black spot of mango, bacterial leaf spot of pepper, bacterial blight of poinsettia, angular leaf spot of cotton, bacterial leaf blotch of soybean, black rot of cruciferae, bacterial wilt of cassava, gummosis of sugarcane, bacterial blight of anthurium, citrus canker pathogen, yellow rot of hyacinth, bacterial leaf spot of strawberry, bacterial canker of poplar, etc.); Agrobacterium (causing crown gall of rosaceous plants, etc.); Xylella (causing Pierce's disease of grapevine and variegated chlorosis of citrus, etc.); Liberibacter (causing huanglongbing of citrus, etc.); Enterobacter (causing wilt pathogen of poplar, etc.); Ligniniphilus (causing bacterial blight of grapevine, etc.).

[0079] Gram-positive bacteria: Corynebacterium (causing potato ring rot, bacterial canker of tomato, bacterial wilt of alfalfa, Stewart's wilt of maize, bacterial mosaic of wheat, etc.); Streptomyces (causing potato common scab, etc.); Curtobacterium (causing bacterial wilt of bean, yellow pustule of tulip, wilt of bean, etc.); Arthrobacter (causing leaf blight of American holly, etc.); Rhodococcus (causing fasciation of sweet pea, etc.); Bacillus (causing Bacillus leaf spot of maize, white leaf streak of wheat, etc.); Rathayibacter (causing honey spike of cocksfoot, etc.).

[0080] According to the embodiments of the present invention, the compound represented by formula (I) or its agrochemically acceptable salt or the composition can be used to control the following pathogenic bacteria or their corresponding diseases: Magnaporthe oryzae, Rhizoctonia solani Kuhn, Ustilaginoidea virens (Cooke) Takahashi, Botrytis cinerea Pers., Rhizoctonia bataticola (Taub.) Butler, Fusarium graminearum Schwabe, Fusarium culmorum (W.G. Sm.) Sacc., Phytophthora citrophthora (R.et E.Sm.) Leon., Rhizoctonia solani Kühn, Sclerotinia sclerotiorum (Lib.) de Bary, Fusarium pseudograminearum, Verticillium tricorpus, Phytophthora infestans (Mont.) de Bary, Gaeumannomyces graminis (Sacc.) Arx & Olivier, Colletotrichum gloeosporioides Penz.

[0081] To obtain the desired effect, the dosage of the compound varies depending on various factors, such as the compound used, the crop to be protected, the type of pest, the degree of infestation, climatic conditions, application method, and the dosage form employed.

[0082] The selection of the dosage form or composition components described herein should be consistent with the physical properties of the active ingredient, the mode of application, and environmental factors such as soil type, humidity, and temperature.

[0083] The dosage forms include liquid formulations such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and / or suspoemulsions), etc., which can optionally be thickened into gels. The dosage forms also include solids such as powders, dusts, granules, tablets, pellets, films, etc., which can be water-dispersible ("wettable") or water-soluble. The active ingredient can be microencapsulated and then formulated into suspensions or solid dosage forms; alternatively, the entire dosage form of the active ingredient can be encapsulated. Encapsulation can control or slow down the release of the active ingredient. Sprayable formulations can be diluted in a suitable medium, and the spray volume used is approximately one hundred to several hundred liters per hectare. High-concentration compositions are mainly used as intermediates for further processing.

[0084] Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, and Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended applications. All formulations may contain small amounts of additives to reduce foaming, prevent caking, prevent corrosion, inhibit microbial growth, etc., or thickeners to increase viscosity.

[0085] Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, silanes, N,N-dialkyl taurates, lignin sulfonates, naphthalene sulfonate-aldehyde condensates, polycarboxylates, and polyoxyethylene / polyoxypropylene block copolymers.

[0086] Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite, and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate, sodium bicarbonate, 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, dodecanol, and tetrahydrofurfuryl alcohol.

[0087] Solutions, including emulsifiable concentrates, can be prepared by simply mixing the components. Dusts and fine powders can be prepared by mixing or, generally, by grinding in a hammer mill or fluid energy mill. Suspension concentrates are generally prepared by wet grinding, for example, by the method described in US 3060084. Granules and pellets are prepared by spraying the active substance onto freshly prepared granular carriers or by granulation techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, 147-48; Perry's Chemical Engineer's Handbook, 4TH Ed., McGraw-Hill, New York, 1963, 8-57; and WO 9113546. Pellets are prepared as described in US 4172714, and water-dispersible and water-soluble granules are prepared by the methods described in US 4144050, US 3920442, and DE 3246493. Tablets are prepared by the methods described in US 5180587, US 5232701, and US 5208030. Films are prepared by the methods described in GB 2095558 and US 3299566.

[0088] More information on processing can be found in US 3235361, column 6, lines 16 to column 7, line 19, and Examples 10-41; US 3309192, column 5, line 43 to column 7, line 62, and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, and 169-182; US 2891855, column 3, line 66 to column 5, line 17, and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York 1961, 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.

[0089] In this article, for certain applications of the described compositions, such as in agriculture, one, two, or more other fungicides, insecticides, acaricides, herbicides, plant growth regulators, or fertilizers, etc. can be added to the compositions described in the present invention, whereby additional advantages and effects can be produced.

[0090] Term Definitions and Explanations

[0091] Unless otherwise defined, all technical terms used herein shall have the same meanings as commonly understood by those skilled in the art to which the claimed subject matter pertains. Unless otherwise specified, all patents, patent applications, and published materials cited herein in their entirety are incorporated herein by reference. If there are multiple definitions of a term in this document, the definitions in this chapter shall prevail.

[0092] For the numerical ranges recited in the specification and claims of this application, when the numerical range is only for "integers", it should be understood that both endpoints of the range and each integer within the range are recited. For example, being "1 - 5" should be understood as reciting each of the integers 1, 2, 3, 4, and 5.

[0093] The term "halogen" refers to fluorine, chlorine, bromine, or iodine.

[0094] As used herein, the term "pharmaceutically acceptable salt" refers to a salt that retains the biological potency of the free acid and free base of the specified compound and has no adverse effects biologically or otherwise. The compounds of this application also include pharmaceutically acceptable salts, such as nitrates, hydrochlorides, sulfates, or phosphates, etc. A pharmaceutically acceptable salt refers to converting the base group in the parent compound into the form of a salt. Pharmaceutically acceptable salts include, but are not limited to, inorganic or organic acid salts of base groups such as amine (ammonia) groups. The pharmaceutically acceptable salts of this application can be synthesized from the parent compound, that is, the basic group in the parent compound reacts with 1 - 4 equivalents of an acid in a solvent system.

[0095] The term "C1 - C10 alkyl" should be understood to represent a straight-chain or branched-chain saturated monovalent hydrocarbon group having 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. For example, "C1 - C6 alkyl" represents straight-chain and branched-chain alkyl groups having 1, 2, 3, 4, 5, or 6 carbon atoms. The alkyl groups are, 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, etc., or their isomers. In particular, the groups are straight-chain or branched-chain saturated monovalent hydrocarbon groups having 1, 2, 3, or 4 carbon atoms. The alkyl groups are, for example, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, tert-butyl, or their isomers.

[0096] The above definitions of terms such as "alkyl", e.g., "C1-C4 alkyl", also apply to other terms containing "C1-C4 alkyl", such as the term "C1-C4 haloalkyl", etc.

[0097] The term "haloalkyl" should be understood as a straight-chain or branched-chain alkyl group in which some or all of the hydrogen atoms are replaced by halogen atoms, such as CF3CH2-.

[0098] The term "C 6-20 aryl" should be understood to mean a monocyclic, bicyclic or tricyclic hydrocarbon ring having 6 to 20 carbon atoms and being monovalent, aromatic or partially aromatic, preferably "C 6-14 aryl". The term "C 6-14 aryl" should be understood to preferably mean a monocyclic, bicyclic or tricyclic hydrocarbon ring having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms and being monovalent, aromatic or partially aromatic ("C 6-14 aryl"), especially a ring having 6 carbon atoms ("C6 aryl"), such as phenyl; or biphenyl, or a ring having 9 carbon atoms ("C9 aryl"), such as indanyl or indenyl, or a ring having 10 carbon atoms ("C 10 aryl"), such as tetrahydronaphthyl, dihydronaphthyl or naphthyl, or a ring having 13 carbon atoms ("C 13 aryl"), such as fluorenyl, or a ring having 14 carbon atoms ("C 14 aryl"), such as anthracenyl. When the C 6-20 aryl is substituted, it may be mono-substituted or multi-substituted. Moreover, there is no restriction on the substitution site, for example, it may be ortho-substituted, para-substituted or meta-substituted.

[0099] The term "5-20 membered heteroaryl" should be understood to include such monovalent monocyclic, bicyclic or tricyclic aromatic ring systems, including aromatic or partially aromatic ones, which have 5 to 20 ring atoms and contain 1-5 heteroatoms independently selected from N, O and S, such as "5-14 membered heteroaryl". The term "5-14 membered heteroaryl" should be understood to include such monovalent monocyclic, bicyclic or tricyclic aromatic ring systems: which have 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14 ring atoms, especially 5 or 6 or 9 or 10 carbon atoms, and which contain 1-5, preferably 1-3 heteroatoms independently selected from N, O and S and, additionally, may be benzo-fused in each case. In particular, heteroaryl is selected from thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, thia-4H-pyrazolyl and the like and their benzo derivatives, such as benzofuryl, benzothienyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, benzotriazolyl, indazolyl, indolyl, isoindolyl and the like; or pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl and the like, and their benzo derivatives, such as quinolinyl, quinazolinyl, isoquinolinyl and the like; or azocinyl, indolizinyl, purinyl and the like and their benzo derivatives; or cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl and the like. When the 5-20 membered heteroaryl is linked to other groups to form the compounds of the present invention, it may be that the carbon atoms on the 5-20 membered heteroaryl ring are linked to other groups, or the heteroatoms on the 5-20 membered heteroaryl ring are linked to other groups. When the 5-20 membered heteroaryl is substituted, it may be mono-substituted or multi-substituted. And, there is no restriction on its substitution site, for example, the hydrogen linked to the carbon atom on the heteroaryl ring may be substituted, or the hydrogen linked to the heteroatom on the heteroaryl ring may be substituted.

[0100] The term "3-20 membered heterocyclic group" should be understood to mean a saturated monovalent monocyclic, bicyclic hydrocarbon ring or bridged cycloalkane, the total ring atoms of which contain 1-5 heteroatoms independently selected from N, O and S and the total number of ring atoms is 3-20 (such as 3, 4, 5, 6, 7, 8, 9, 10, etc.), preferably "3-10 membered heterocyclic group". The term "3-10 membered heterocyclic group" means a saturated monovalent monocyclic, bicyclic hydrocarbon ring or bridged cycloalkane, which contains 1-5, preferably 1-3 heteroatoms independently selected from N, O and S, for example 1, 2, 3 heteroatoms independently selected from N, O and S. The heterocyclic group can be linked to the rest of the molecule through any one of the carbon atoms or a nitrogen atom (if present). In particular, the heterocyclic group can include, but is not limited to: 4-membered rings, such as azetidinyl, oxetanyl; 5-membered rings, such as tetrahydrofuranyl, dioxolanyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, pyrroline; or 6-membered rings, such as tetrahydropyranyl, piperidinyl, morpholinyl, dithianyl, thiomorpholinyl, piperazinyl or trithianyl; or 7-membered rings, such as diazepanyl. Optionally, the heterocyclic group can be benzo-fused. The heterocyclic group can be bicyclic, for example but not limited to 5,5-membered rings, such as hexahydrocyclopenta[c]pyrrol-2(1H)-yl ring, or 5,6-membered bicyclic rings, such as hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl ring. The ring containing a nitrogen atom can be partially unsaturated, that is, it can contain one or more double bonds, such as but not limited to 2,5-dihydro-1H-pyrrolyl, 4H-[1,3,4]thiadiazinyl, 4,5-dihydrooxazolyl or 4H-[1,4]thiazinyl, or it can be benzo-fused, such as but not limited to dihydroisoquinolinyl. According to the present invention, the heterocyclic group is non-aromatic. When the 3-20 membered heterocyclic group is linked to other groups to form the compounds of the present invention, it can be the carbon atom on the 3-20 membered heterocyclic group linked to other groups, or the heteroatom on the 3-20 membered heterocyclic ring linked to other groups. For example, when the 3-20 membered heterocyclic group is selected from piperazinyl, it can be the nitrogen atom on piperazinyl linked to other groups. Or when the 3-20 membered heterocyclic group is selected from piperidinyl, it can be the nitrogen atom and the carbon atom at its para position on the piperidinyl ring linked to other groups.

[0101] The term "3- to 20-membered cycloalkyl" refers to a saturated or partially unsaturated monocyclic or polycyclic cyclic hydrocarbon group, the carbocyclic ring of which may contain 3 to 20 carbon atoms, preferably 3 to 12 (e.g., 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) carbon atoms, more preferably 3 to 6 carbon atoms. The carbocyclic ring may be monocyclic or polycyclic, and it may be a saturated cycloalkyl or may optionally contain one, two or more double bonds and / or triple bonds in its ring, thereby forming a so-called cycloalkenyl or cycloalkynyl. In the case of having multiple rings, these rings may form spiro, fused and bridged ring structures. For example, non-limiting examples of monocyclic carbocyclic rings include cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cycloheptatrienyl, cyclooctyl, cyclooctatetraenyl, etc.; non-limiting examples of polycyclic carbocyclic rings include decahydronaphthyl or isobornyl.

[0102] Unless otherwise specified, a heterocyclic group, heteroaryl or heteroarylene includes all its possible isomeric forms, such as its positional isomers. Thus, for some illustrative non-limiting examples, it may include forms substituted or bonded to other groups at one, two or more positions among its 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12- positions, etc. (if present), including pyridin-2-yl, pyridin-2-ylidene, pyridin-3-yl, pyridin-3-ylidene, pyridin-4-yl and pyridin-4-ylidene; thienyl or thienylidene includes thien-2-yl, thien-2-ylidene, thien-3-yl and thien-3-ylidene; pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl.

[0103] Beneficial effects

[0104] The compounds represented by formula (I) of the present invention exhibit good activity against various pathogens in the fields of agronomy and horticulture. Moreover, these compounds can achieve good control effects at very low doses, and thus can be used to prepare fungicides.

[0105] In addition, the preparation steps of the compounds of the present invention are simple and the yields are relatively high, so they have good application prospects. Detailed implementation manners

[0106] The technical solutions of the present invention will be further described in detail below in conjunction with specific embodiments. It should be understood that the following embodiments are only for illustrative explanation of the present invention and should not be construed as limiting the protection scope 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.

[0107] Unless otherwise specified, the raw materials and reagents used in the following embodiments are all commercially available products or can be prepared by known methods.

[0108] The following method is used for LC-MS analysis:

[0109] Chromatographic column: Agilent ZORBAX SB-C18 150 mm × 4.6 mm, 5 μm (inner diameter);

[0110] Detection wavelength: 254 nm;

[0111] Flow rate: 0.8 mL / min;

[0112] Column temperature: 30 °C;

[0113] Gradient elution conditions:

[0114]

[0115] Synthesis examples

[0116] Example 1: 3-(3-(4-(((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)phenyl)prop-1-yn-1-yl)pyridin-2-amine (Compound 3)

[0117]

[0118] First step: Preparation of methyl 4-(((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)benzoate (Intermediate 1)

[0119] At room temperature, 5.0 g (30 mmol) of methyl 4-(hydroxymethyl)benzoate and 6.50 g (30 mmol) of 2,3-dichloro-5-trifluoromethylpyridine were successively dissolved in 60 mL of acetonitrile. 12.50 g (90 mmol) of potassium carbonate was added to the above mixture, and the mixture was heated under reflux and stirred for 8 h. After distillation under reduced pressure, 50 ml of water was added to the residue, and the mixture was extracted with ethyl acetate (2 × 30 mL). The organic layers were combined, washed with 20 mL of saturated brine, and dried over anhydrous magnesium sulfate. After evaporation under reduced pressure, column chromatography (eluent: a mixture of ethyl acetate and petroleum ether (1:6)) gave 5.80 g of the product with a yield of 56%.

[0120] LC / MS [M+H] + = 346.05, [M+Na] + = 368.03, [M+K] + = 384.00.

[0121] Second step: Preparation of 4-(((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)phenyl)methanol (Intermediate 2)

[0122] At room temperature, 5.0 g (14.4 mmol) of methyl 4-(((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)benzoate (Intermediate 1) was dissolved in tetrahydrofuran (30 ml). After purging with nitrogen, the temperature of the system was lowered to 0 °C, and 1.09 g (28.8 mmol) of lithium aluminum hydride was added portionwise. The reaction solution was stirred for 2 h. The reaction solution was slowly added to a potassium bisulfate solution (30 ml), stirred for 20 min, and extracted with ethyl acetate (3 × 30 mL). The organic layers were combined, washed with saturated brine (20 mL), and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and column chromatography (eluent: a mixture of ethyl acetate and petroleum ether (1:5)) gave 4.26 g of the product with a yield of 93%.

[0123] LC / MS[M+H] + = 318.05, [M+Na] + = 340.03, [M+K] + = 356.01.

[0124] Step 3: Preparation of 3-chloro-2-((4-(chloromethyl)phenyl)oxy)-5-(trifluoromethyl)pyridine (Intermediate 3)

[0125] At 0 °C, 4.0 g (12.6 mmol) of 4-(((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)phenyl)methanol (Intermediate 2) was added to thionyl chloride (25 ml). The reaction solution was heated to 40 °C and stirred for 2 h. The reaction solution was concentrated under reduced pressure to obtain a crude product, which was added to a saturated sodium bicarbonate solution (80 ml), and extracted with ethyl acetate (3 × 40 mL). The organic layers were combined, washed with saturated brine (20 mL), and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 4.0 g of the product with a yield of 95%.

[0126] LC / MS[M+H] + = 336.02, [M+Na] + = 358.00, [M+K] + = 373.97.

[0127] Step 4: Preparation of bis(tert-butyl) (3-(3-(4-(((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)phenyl)prop-1-yn-1-yl)pyridin-2-ylcarbamate (Intermediate 5)

[0128] At room temperature, 1.0 g (3 mmol) of 3-chloro-2-((4-(chloromethyl)phenyl)oxy)-5-(trifluoromethyl)pyridine (Intermediate 3) and 0.95 g (3 mmol) of bis(tert-butyl)(3-ethynylpyridin-2-yl)carbamate (Intermediate 4) were dissolved in acetonitrile (30 ml). 1.95 g (6 mmol) of cesium carbonate, 0.28 g (0.6 mmol) of Xphos, and 0.08 g (0.3 mmol) of Pd(CH3CN)2Cl2 were added. The reaction solution was heated to 90 °C under nitrogen protection and stirred for 4 h. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure to obtain a crude product. Column chromatography (eluent: a mixed solution of ethyl acetate and petroleum ether (1:2)) gave 1.16 g of the product, with a yield of 63%.

[0129] LC / MS [M+H] + = 618.20, [M+Na] + = 640.18, [M+K] + = 656.15.

[0130] Step 5: Preparation of 3-(3-(4-(((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)phenyl)prop-1-yn-1-yl)pyridin-2-amine (Compound 3)

[0131] 1.0 g (1.6 mmol) of bis(tert-butyl)(3-(3-(4-(((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)phenyl)prop-1-yn-1-yl)pyridin-2-yl)carbamate (Intermediate 5) was dissolved in 4.8 g (104 mmol) of formic acid and stirred at 15 °C for 15 h. The reaction solution was directly concentrated to obtain a crude product. Column chromatography (eluent: a mixed solution of ethyl acetate and petroleum ether (1:1)) gave 0.43 g of the product, with a yield of 65%.

[0132] LC / MS [M+H] + = 418.10, [M+Na] + = 440.08, [M+K] + = 456.05. 1 H NMR (400 MHz, CDCl3): δ 8.02 - 8.00 (m,

[0133] 1H), 7.88 (s, 1H), 7.67 - 7.64 (m, 1H), 7.55 (s, 1H), 7.19 (d, 2H), 7.13 (d, 2H), 6.78 (s, 2H), 6.59 - 6.55 (m, 1H), 5.10 (s, 2H), 3.32 (s, 2H). 1313C NMR (100 MHz, CDCl3) δ 163.0, 159.4, 149.0, 148.9, 142.3, 139.6, 138.5, 134.8, 130.3 128.1, 125.1, 122.2, 118.9 117.7, 103.1, 88.1, 69.6, 50.5, 23.6.

[0134] Other compounds of the present invention were synthesized by referring to the above method.

[0135] The structural characterization data of some compounds of formula (I) are as follows:

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146] Formulation Examples

[0147] In the following examples, all percentages are by weight, and all dosage forms are prepared by conventional methods.

[0148] Example 2:

[0149] In this example, a wettable powder was prepared using the compound obtained in the above example, and it was specifically prepared with the following raw material composition in the following ratio:

[0150] Compound 1 60.0%, dodecylphenol polyethoxyethylene glycol ether 4.0%, sodium lignosulfonate 5.0%, sodium aluminosilicate 6.0%, montmorillonite (calcined) 25.0%.

[0151] Example 3:

[0152] In this example, a granule was prepared using the compound obtained in the above example, and it was specifically prepared with the following raw material composition in the following ratio:

[0153] Compound 2: 10.0%, other components: sodium dodecyl sulfate 2%, calcium lignosulfonate 6%, potassium chloride 10%, polydimethylsiloxane 1%, soluble starch to make up 100%.

[0154] Example 4:

[0155] In this example, the compound obtained in the above example was used to prepare extrusion pellets, and the raw material composition with the following specific ratio was used for preparation:

[0156] Compound 3: 25.0%, anhydrous calcium sulfate 10.0%, crude calcium lignosulfonate 5.0%, alkylnaphthalenesulfonate 1.0%, calcium / magnesium bentonite 59.0%.

[0157] Example 5:

[0158] In this example, the compound obtained in the above example was used to prepare emulsifiable concentrate, and the raw material composition with the following specific ratio was used for preparation:

[0159] Compound 4: 25.0%, solvent 150 60%, PEG400 5%, Rhodacal 70 / B 3%, Rhodameen RAM / 7 7%.

[0160] Example 6:

[0161] In this example, the compound obtained in the above example was used to prepare water suspension concentrate, and the raw material composition with the following specific ratio was used for preparation:

[0162] Compound 10: 30.0%, POE polystyrene phenyl ether sulfate 5.0%, xanthan gum 0.5%, polyethylene glycol 5%, triethanolamine 1%, sorbitol 0.5%, water to make up 100.0%.

[0163] Biological activity determination

[0164] The compounds of the present invention show good activity against various pathogens in the fields of agronomy and horticulture.

[0165] Example 7: Fungicidal activity determination

[0166] In vitro antibacterial activity tests of the compounds of the present invention against various fungal diseases of plants were carried out. The results of fungicidal activity determination are shown in the following examples.

[0167] The test method is as follows: Dissolve the sample of the compound to be tested with a suitable solvent (the types of solvents such as acetone, methanol, DMSO, etc., and select according to its solubility in the sample) to prepare a test solution with the required concentration. Under a super-clean working environment, add the test solution into the micro-wells of a 96-well culture plate, and then add the suspension of the pathogen propagules into it. The treated culture plate is placed in a constant-temperature incubator for cultivation. After 24 hours, conduct an investigation. During the investigation, visually observe the germination or growth of the pathogen propagules, and evaluate the antibacterial activity of the compound according to the germination or growth of the control treatment.

[0168] (1) The test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compound against Magnaporthe oryzae are as follows:

[0169] At a dose of 10 ppm, the compounds with an inhibition rate against Magnaporthe oryzae above 80% are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0170] At a dose of 1 ppm, the compounds with an inhibition rate against Magnaporthe oryzae above 80% are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0171] (2) The test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compound against Rhizoctonia solani are as follows:

[0172] At a dose of 10 ppm, the compounds with an inhibition rate against Rhizoctonia solani above 80% are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0173] Compounds with an inhibition rate of over 80% against Rhizoctonia solani at a dose of 1 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0174] (3) Test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compounds against Ustilaginoidea virens are as follows:

[0175] Compounds with an inhibition rate of over 80% against Ustilaginoidea virens at a dose of 10 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0176] Compounds with an inhibition rate of over 80% against Ustilaginoidea virens at a dose of 1 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0177] (4) Test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compounds against Botrytis cinerea are as follows:

[0178] Compounds with an inhibition rate of over 80% against Botrytis cinerea at a dose of 10 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0179] Compounds with an inhibition rate of over 80% against Botrytis cinerea of tomatoes at a dose of 1 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0180] (5) Test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compounds against Fusarium solani of peanuts are as follows:

[0181] Compounds with an inhibition rate of over 80% against Fusarium solani of peanuts at a dose of 10 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0182] Compounds with an inhibition rate of over 80% against Fusarium solani of peanuts at a dose of 1 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0183] (6) Test results of the in vitro antibacterial activity (expressed as inhibition rate) of some compounds against Gibberella zeae of wheat are as follows:

[0184] Compounds with an inhibition rate of over 80% against Gibberella zeae of wheat at a dose of 10 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0185] Compounds with an inhibition rate of over 80% against Gibberella zeae at a dose of 1 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0186] (7) Test results of the in vitro antibacterial activities (expressed as inhibition rate) of some compounds against Fusarium culmorum are as follows:

[0187] Compounds with an inhibition rate of over 80% against Fusarium culmorum at a dose of 10 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0188] Compounds with an inhibition rate of over 80% against Fusarium culmorum at a dose of 1 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0189] (8) Test results of the in vitro antibacterial activities (expressed as inhibition rate) of some compounds against Phomopsis citri are as follows:

[0190] Compounds with an inhibition rate of over 80% against Phomopsis citri at a dose of 10 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0191] Compounds with an inhibition rate of over 80% against Phytophthora citrophthora at a dose of 1 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0192] (9) Test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compounds against Rhizoctonia solani are as follows:

[0193] Compounds with an inhibition rate of over 80% against Rhizoctonia solani at a dose of 10 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0194] Compounds with an inhibition rate of over 80% against Rhizoctonia solani at a dose of 1 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0195] (10) Test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compounds against Sclerotinia sclerotiorum are as follows:

[0196] Compounds with an inhibition rate of over 80% against Sclerotinia sclerotiorum at a dose of 10 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0197] At a dose of 1 ppm, the compounds with an inhibition rate of over 80% against Sclerotinia sclerotiorum are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0198] (11) The test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compounds against Fusarium pseudograminearum are as follows:

[0199] At a dose of 10 ppm, the compounds with an inhibition rate of over 80% against Fusarium pseudograminearum are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0200] At a dose of 1 ppm, the compounds with an inhibition rate of over 80% against Fusarium pseudograminearum are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0201] (12) The test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compounds against Verticillium neo - nubilum are as follows:

[0202] At a dose of 10 ppm, the compounds with an inhibition rate of over 80% against Verticillium neo - nubilum are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0203] At a dose of 1 ppm, the compounds with an inhibition rate of over 80% against Verticillium dahliae Kleb. on maize are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0204] (13) The test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compounds against Phytophthora infestans are as follows:

[0205] At a dose of 10 ppm, the compounds with an inhibition rate of over 80% against Phytophthora infestans are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0206] At a dose of 1 ppm, the compounds with an inhibition rate of over 80% against Phytophthora infestans are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0207] (14) The test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compounds against Gaeumannomyces graminis var. tritici are as follows:

[0208] At a dose of 10 ppm, the compounds with an inhibition rate of over 80% against Gaeumannomyces graminis var. tritici are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0209] Compounds with an inhibition rate of over 80% against Gaeumannomyces graminis var. tritici at a dose of 1 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0210] (15) The test results of the in vitro antibacterial activity (expressed as inhibition rate) of the compounds against Colletotrichum gloeosporioides are as follows:

[0211] Compounds with an inhibition rate of over 80% against Colletotrichum gloeosporioides at a dose of 10 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0212] Compounds with an inhibition rate of over 80% against Colletotrichum gloeosporioides at a dose of 1 ppm are: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56.

[0213] The above describes the embodiments of the present invention. However, the present invention is not limited to the above embodiments. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention shall be included within the protection scope of the present invention.

Claims

1. A pyridineamine compound represented by formula (I) or a pharmaceutically acceptable salt thereof, Among them, R1 is the same or different and each independently selected from hydrogen, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 haloalkyl, C1-C 10 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; R2 is the same or different and each independently selected from hydrogen, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 haloalkyl, C1-C 10 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; R a and R b are the same or different and are each independently selected from hydrogen, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 haloalkyl, C1-C 10 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; Y is selected from -O-, -S-, -Se-, -CH2-, -CH2O-, -OCH2-, -CH2S-, -SCH2-; Q is selected from C6-20 aryl optionally substituted with one, two or more Rs, 5-20 membered heteroaryl, 3-20 membered cycloalkyl, 3-20 membered heterocycloalkyl, s1 and R s1 identical or different and each independently selected from the following groups: hydrogen, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 haloalkyl, C1-C 10 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; p is an integer selected from 0, 1, 2, 3; q is an integer selected from 0, 1, 2, 3, 4; Indicates the attachment site of the group; Provided that the compound represented by formula (I) does not include the following compounds:

2. The compound or its pharmaceutically acceptable salt according to claim 1, wherein R1 are the same or different and are independently selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; Preferably, R2 are the same or different and are independently selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; Preferably, R a , R b are the same or different and each independently selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, halogen, hydroxy, amino, nitro, cyano; Preferably, Y is selected from -O-, -S-, -CH2O-, -OCH2-, -CH2S-, -SCH2-; Preferably, Q is selected from C6-16 aryl, 5-16 membered heteroaryl, 3-16 membered cycloalkyl, 3-16 membered heterocycloalkyl, optionally substituted by one, two or more Rs s1 and 3-16 membered heterocycloalkyl, optionally substituted by one, two or more Rs 3. The compound according to claim 1 or 2, or a pharmaceutically acceptable salt thereof, characterized in that, Q is selected from phenyl, naphthyl, pyrrolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazolinyl, triazinyl optionally substituted with one, two or more Rs s1 or Preferably, R s1 are the same or different and are each independently selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, halogen, hydroxy, amino, nitro, cyano.

4. The compound according to any one of claims 1-3 or a pharmaceutically acceptable salt thereof, characterized in that, Q is selected from R s1 has the definition according to any one of claims 1-3; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7; Preferably, Q is selected from 5. The compound according to any one of claims 1-4 or a pharmaceutically acceptable salt thereof, characterized in that, The compound represented by formula (I) is selected from the compound represented by the following formula (II) or a pharmaceutically acceptable salt thereof: wherein, R1 is selected from hydrogen, C1-C 10 alkyl, C1-C 10 alkoxy, C1-C 10 haloalkyl, C1-C 10 haloalkoxy, halogen, hydroxyl, amino, nitro, cyano; Y and Q have the definitions as described in any one of claims 1-4.

6. The compound according to any one of claims 1-5 or a pharmaceutically acceptable salt thereof, characterized in that, The compound of formula (I) is selected from the following compounds or a pharmaceutically acceptable salt thereof, 7. A method for preparing the compound of formula (I) or a pharmaceutically acceptable salt thereof according to any one of claims 1-6, the preparation method comprising: 1) Reacting the compound represented by formula (VIII) with the compound represented by formula (IX) to obtain the compound represented by formula (VII); 2) Reacting the compound represented by formula (VII) to obtain the compound represented by formula (VI); 3) Reacting the compound represented by formula (VI) to obtain the compound represented by formula (V); 4) Reacting the compound represented by formula (V) with the compound represented by formula (IV) to obtain the compound represented by formula (III); 5) Reacting the compound represented by formula (III) to obtain the compound represented by formula (I); The reaction formula is as follows: Among them, R1, R2, R a , R b , Y, Q, p, q have the definitions described in any one of claims 1-6; L1 and L2 are selected from leaving groups.

8. A composition, the composition comprising at least one of the compound represented by formula (I) according to any one of claims 1-6 or a pharmaceutically acceptable salt thereof as an active ingredient.

9. Use of the compound represented by formula (I) according to any one of claims 1-6 or a pharmaceutically acceptable salt thereof, or the composition according to claim 8 in the preparation of a fungicide for use in the agronomic field or the horticultural field.

10. A method for controlling germs or diseases in the agronomic field or the horticultural field, the method comprising applying an effective amount of at least one of the compound represented by formula (I) according to any one of claims 1-6 or a pharmaceutically acceptable salt thereof, or the composition according to claim 8 to the growth medium of the germs or diseases.

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