Methylene ester bridge-containing compound and preparation method and bactericide application thereof

Abstract

The invention relates to a methylene ester bridge-containing compound as well as a preparation method and a bactericide application thereof. The compound has a structure as shown in a formula (I). The compound disclosed by the invention has broad-spectrum bactericidal activity on various plant fungal diseases, can be used for preventing and treating various plant fungal diseases independently or by being compounded with other medicaments, and particularly has an excellent preventing and treating effect on rice sheath blight disease, cucumber gray mold, wheat scab and sclerotinia rot of colza.

Description

Technical Field

[0001] This invention relates to the field of pesticide chemistry, specifically to a methylene ester-bridged compound, its preparation method, and its application as a fungicide. Background Technology

[0002] Fungal diseases not only affect food security but also threaten biodiversity. To prevent plant diseases and reduce the losses they cause, numerous antifungal and fungicidal compounds have been reported and applied. Among existing fungicides, ester-based fungicides account for only a minority, and they are not the main active fragments.

[0003] Developing a methylene ester-containing structure as an active fragment for the control of plant fungi is a novel design concept. While maintaining efficacy, the ester bond is easily hydrolyzed within the plant, thus often avoiding phytotoxicity. Therefore, designing and developing highly efficient, highly active, and low-toxicity fungicides using methylene esters as the backbone is the technical problem this invention aims to solve. Summary of the Invention

[0004] The purpose of this invention is to provide a methylene ester-bridged compound that can be used as a fungicide in the field of agronomy.

[0005] In a first aspect of the invention, a methylene ester-bridged compound, and its optical isomers, cis-trans isomers, or pesticide-acceptable salts thereof, are provided, said compound having the structure shown in formula (I):

[0006]

[0007] Wherein, A is independently selected from the group consisting of: phenyl, -(C1-C8 alkylene)phenyl, -N=CH-phenyl; wherein one or more hydrogen atoms on A are optionally substituted by Ra, wherein Ra is selected from the group consisting of: halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C8 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 thioalkyl;

[0008] T is independently: halogen, hydroxyl, nitro, amino, cyano, or a substituted or unsubstituted group selected from the group consisting of: C1-C8 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 alkenoxy, C2-C6 alkynoxy, C1-C6 alkoxy, C3-C6 cycloalkoxy, C5-C7 cycloalkenyl, C3-C 10 Cycloalkyl, 4-8 membered heterocyclic, C6-C 10 Aryl, 5-8 membered aromatic heterocyclic, -(C1-C8 alkylene)(C6-C10 aryl), -(C6-C 10 aryl)-O-(C6-C 10 aryl), -(C6-C 10 aryl)-(C6-C 10 aryl), -(C1-C8 alkylene)(5-10 heteroaryl), -OC(=O)(C6-C 10 aryl), -OC (=O)(C6-C 10 Aryl)(C2-C6 alkenyl), -OC(=O)(C1-C8 alkylene)(C6-C 10 Aryl), -OC(=O)(C1-C8 alkylene)phenyl(C2-C6 alkenyl), -(C1-C8 alkylene)(C3-C6 cycloalkyl), -(C1-C8 alkylene)(4-10 heterocyclic), -(C1-C8 alkylene)NHC(=O)(4-10 heteroaryl);

[0009] W is independently: cyano, substituted or unsubstituted groups selected from the group consisting of C1-C1. 10 Alkyl, C2-C6 alkenyl, C2-C6 ynyl, C6-C 10 Aryl, 5-8 membered heteroaryl, 4-8 membered heterocyclic, C3-C 10 Cycloalkyl, -(C1-C8 alkylene)(C3-C 10 cycloalkyl), -(C1-C8 alkylene)(C6-C 10 aryl), -(C1-C8 alkylene)(4-10 heteroaryl), -(C1-C8 alkylene)(4-8 heterocyclic), -O(C1-C 10 Alkyl), -O (C3-C) 10 cycloalkyl), -O (C6-C) 10 aryl), -O (4-10 membered heteroaryl), -O (4-8 membered heterocyclic), -NH (C1-C 10 Alkyl), -NH (C3-C) 10 cycloalkyl), -NH (C6-C 10 Aryl), -NH (4-10 membered heteroaryl), -NH (4-8 membered heterocyclic);

[0010] Unless otherwise specified, substitution means that one or more hydrogen atoms on a group are substituted by a substituent selected from the group consisting of: deuterium, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 alkoxy, halo-C1-C4 alkyl, and halo-C1-C4 alkoxy.

[0011] In another preferred embodiment, the compound has the structures shown in formulas (IA) and (IB):

[0012]

[0013] Wherein, R1 is selected from the group consisting of: halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C8 alkyl; m and n are each independently an integer between 0 and 5;

[0014] The remaining substituents are as described above.

[0015] In another preferred embodiment, A is: -CF3,

[0016] In another preferred embodiment, each of the following groups, T, is independently: halogen, hydroxyl, nitro, amino, cyano, C1-C4 alkyl, halogenated C1-C4 alkyl, C2-C4 alkenyl, halogenated C2-C4 alkenyl, C2-C4 alkynyl, halogenated C2-C4 alkynyl, C2-C4 alkenoxy, halogenated C2-C4 alkenoxy, C2-C4 alkynoxy, C1-C4 alkoxy, or substituted or unsubstituted groups of the following: C3-C7 cycloalkyl, five-membered heterocyclic, phenyl, 5-8-membered aromatic heterocyclic, biphenyl, naphthyl.

[0017] In another preferred embodiment, each of the following groups (T) is independently: halogen, hydroxyl, nitro, amino, cyano, methyl, ethyl, propyl, isopropyl, ethynyl, propynyl, butynyl, ethoxy, propoxy, isopropoxy, propynylated, fluoroethynyl, bromoethynyl, chloroethynyl, fluoropropynyl, bromopropynyl, chloropropynyl, fluorobutynyl, bromobutynyl, chlorobutynyl, trifluoromethyl, difluoromethyl, etc.

[0018] Where X is selected from: F, Cl, Br, I, CF3, OCF3, OCH3;

[0019] o and p are selected from 0, 1, 2, 3, 4, and 5.

[0020] In another preferred embodiment, each of the W groups is independently: cyano, C1-C4 alkyl, halo-C1-C4 alkyl, or substituted or unsubstituted of the following groups: C3-C7 cycloalkyl, phenyl, 5-8 membered aromatic heterocyclic group.

[0021] In another preferred embodiment, each of the W groups is independently: cyano, -CF3, -CH2CF3, -CH2CH2CF3,

[0022] Y is selected from: F, Cl, Br, I;

[0023] q is selected from 0, 1, 2, 3, 4, 5.

[0024] In another preferred embodiment, the compound is selected from the following table:

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] In a second aspect, the present invention provides a pesticide composition, wherein

[0040] Contains: (a) the compound as described in the first aspect of the invention, its optical isomer, cis-trans isomer, or a pesticide-acceptable salt thereof, or a combination thereof; and

[0041] Optional (b) pesticide-acceptable carriers and / or excipients.

[0042] In another preferred embodiment, component (a) accounts for 0.001-99.99 wt% of the total weight of the pharmaceutical composition; more preferably 0.01-99.9 wt%; and even more preferably 0.05-90 wt%.

[0043] In another preferred embodiment, the pesticide composition further includes a fungicide selected from the group consisting of: cyprodinil, fluazinam, flumorph, dimethomorph, chlorothalonil, sulfadiazine, mesotriazine, thiabendazole, cyclofludioxazone, streptomycin, pyrimethanil, cyclooxygenase, benzyloxygenase, cyprothiophanate-methyl, thiabendazole, cyprothiophanate-methyl, diclofenac, cymoxanil, high-efficiency metalaxyl, high-efficiency benzyloxygenase, carbendazim, furazolidone, mesotriazine, fluopyram, azoxystrobin, oxadiazon, pyraclostrobin, pyraclostrobin, fluopyram, tebuconazole, fenoxystrobin, tebuconazole, azoxystrobin, oxadiazon. Azoxystrobin, fluopyram, high-efficiency imidacloprid, imidacloprid, cyazofamid, imidacloprid, prochloraz, oxadiazon, malathion, isoprothiolane, oxytetracycline, flutriafol, fluquinazole, difenoconazole, tetraflufenazole, tebuconazole, flusilazole, silfluzoxystrobin, triazole, bifenthrin, cyproconazole, high-efficiency tebuconazole, tebuconazole, fenbendazole, hexaconazole, prothioconazole, tebuconazole, cyproconazole, cyproconazole, imidacloprid, tebuconazole; Thiazoles: thiamethoxam, benzylthiocyanate, octothiazoline, carbendazim, dodecyl morpholine, butyl morpholine, tridemorpholine; Pyrroles: seed dressing powder Fludioxonil, fluazinam, pyridaben, cyclopyridamenil, pyridabenoxime, pyrimidinium cyclomethonium, chlorophenazine alcohol, fluphenazine alcohol, pyrimethanil, pyrimethanil hydrazone, pyrimethanil, fluazinam, fenpyraclostrobin, difenoconazole, ethoxyquinoline, propoxyquinoline, phenoxyquinoline, isopropoxynil, ethoxycarb, bensulfuron-methyl, thiophanate-methyl, isopyram, pyraclostrobin, methyl thiophanate, fenpyroximate, kasugamycin, polyoxin, polyoxin, activated ester, indole ester, bromonitol, benzylsulfamethoxam, toluenesulfonamide, spirocyclamide, pyrazosulfuron, sodium dichloroisocyanurate, pendimethalin Tetrachlorophthalide, tricyclazole, allylphenthiazide, benzyl sulfadiazine, chlornitramine, biguanide octylamine, doxycycline, cymoxanil, cymoxanil, streptomycin, metalaxyl, propineb, benzyl sulfadiazine, chlorpyrifos, methyl thiophanate, carbendazim, benomyl, captan, thiophanate-methyl, chlorpyrifos, chlorpyrifos, furazolidone, fluchlorochlorothiazide, vinazolidone, thiram, isoprothiolane, isoprothiolane, chlorothalonil, eugenol, carvacrol, berberine.

[0044] In a third aspect, the present invention provides the use of a compound as described in the first aspect of the present invention, its optical isomer, cis-trans isomer, or a pesticide composition as described in the second aspect of the present invention, for the preparation of a fungicide.

[0045] In another preferred embodiment, the fungicide controls the following diseases: gray mold (tomato gray mold, pepper gray mold, leek gray mold, kiwi gray mold, strawberry gray mold, cucumber gray mold, etc.), cucumber anthracnose, downy mildew (cucumber downy mildew, rapeseed downy mildew, soybean downy mildew, beet downy mildew, sugarcane downy mildew, tobacco downy mildew, pea downy mildew, loofah downy mildew, winter melon downy mildew, cantaloupe downy mildew), white rust (rapeseed white rust, ... White rust of cabbage, damping-off (rapeseed damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber damping-off, cotton seedling damping-off), cottony rot (pepper cottony rot, loofah cottony rot, winter melon cottony rot), blight (blight of broad bean, cucumber, winter melon, watermelon, cantaloupe, pepper, leek blight, garlic blight, cotton blight), late blight (potato late blight, tomato late blight), etc.Root rot (root rot of peppers, eggplants, beans, cucumbers, bitter gourds, cotton, broad beans), damping-off (dampness of cotton seedlings, sesame, peppers, cucumbers, cabbage), Verticillium wilt (Verticillium wilt of cotton, sunflowers, tomatoes, peppers, eggplants), black spot (black spot of zucchini, winter melon, cantaloupe), brown spot (brown spot of cotton, jute, beetroot, peanuts, peppers, winter melon, soybeans, sunflowers, peas, broad beans), black spot (false black spot of flax, rapeseed, sesame, sunflowers, castor beans, tomatoes). Black spot disease in various vegetables and crops, including peppers, eggplants, beans, cucumbers, celery, carrots, apples, and peanuts; leaf spot disease in tomatoes, peppers, and celery; early blight in tomatoes, peppers, eggplants, potatoes, and celery; ring rot in soybeans, sesame, and beans; leaf blight in sesame, sunflowers, watermelons, and melons; stem base rot in tomatoes and beans; and others such as corn spot, rice blast, millet black sheath disease, sugarcane eye spot, cotton boll blight, peanut crown rot, soybean stem rot, soybean black spot, melon large leaf spot, peanut net spot, and tea red leaf spot. Pepper white spot, winter melon leaf spot, sprout black rot, Chinese cabbage heart rot, kenaf leaf mold, kenaf spot, jute stem spot, soybean purple spot, sesame leaf spot, castor bean gray spot, tea brown leaf spot, eggplant brown round star disease, common bean red spot, bitter gourd white spot, watermelon spot, jute blight, sunflower root and stem rot, common bean anthracnose, eggplant stem leaf spot, cucumber target spot, tomato leaf mold, eggplant leaf mold, broad bean red spot, etc.; Basidiomycete diseases, such as rust (wheat stripe rust, wheat stem rust, wheat leaf rust, flower rust, sunflower rust, ganlu rust, leek rust, onion rust, chestnut rust, soybean rust, corn rust), smut (corn silk smut, corn smut, sorghum silk smut, sorghum loose smut, sorghum hard smut). Diseases include: ear blight, sorghum smut, millet smut, sugarcane smut, and bean rust; and others such as wheat sheath blight and rice sheath blight; ascomycete diseases, such as powdery mildew (wheat powdery mildew, lettuce powdery mildew, sesame powdery mildew, sunflower powdery mildew, beet powdery mildew, eggplant powdery mildew, pea powdery mildew, loofah powdery mildew, pumpkin powdery mildew, zucchini powdery mildew, winter melon powdery mildew, cantaloupe powdery mildew, grape powdery mildew, and broad bean powdery mildew); sclerotinia rot (rapeseed sclerotinia rot, soybean sclerotinia rot, peanut sclerotinia rot, tobacco sclerotinia rot, pepper sclerotinia rot, and eggplant sclerotinia rot); black spot (apple black spot and pear black spot); and clubroot (cabbage clubroot, Chinese cabbage clubroot, cauliflower clubroot, mustard clubroot, radish clubroot, turnip clubroot, and rapeseed clubroot).

[0046] In another preferred embodiment, the fungicide controls the following diseases: cucumber downy mildew, apple rot, cucumber gray mold, corn rust, soybean rust, rice sheath blight, wheat powdery mildew, wheat scab, rapeseed sclerotinia rot, and rice blast.

[0047] In a fourth aspect, the present invention provides a method for controlling plant pathogens, comprising applying to the environment, soil, or plants requiring control a compound as described in the first aspect of the present invention, its optical isomer, cis-trans isomer, or a pesticide composition as described in the second aspect of the present invention, an optically acceptable salt thereof, or an optically acceptable salt thereof, or to the environment, soil, or plants requiring control.

[0048] It should be understood that, within the scope of this invention, the above-described technical features of this invention and the technical features specifically described below (such as in the embodiments) can be combined with each other to form new or preferred technical solutions. Due to space limitations, they will not be described in detail here. Detailed Implementation

[0049] Through extensive and in-depth research, and through numerous screenings and tests, the inventors have developed a compound containing a methylene ester bridge. This compound exhibits multiple antifungal activities, showing significant inhibitory effects not only on rice sheath blight and cucumber gray mold, but also on wheat scab and rapeseed sclerotinia stem rot. It is expected to be used as a novel pesticide in agricultural production.

[0050] the term

[0051] Group definition

[0052] The term "C1-C8 alkyl" refers to a straight-chain or branched alkyl group having 1 to 8 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or similar groups.

[0053] The term "C2-C6 alkenyl" refers to a straight-chain or branched alkenyl group having 2-6 carbon atoms, such as vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl or similar groups.

[0054] The term "C2-C6 ynyl" refers to a straight-chain or branched ynyl group having 2-6 carbon atoms, such as ethynyl, propynyl, or similar groups.

[0055] The term "C3-C6 cycloalkyl" refers to cyclic alkyl groups having 3-7 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or similar groups.

[0056] The term "C5-C7 cycloalkenyl" refers to a cyclic alkenyl group having 5-7 carbon atoms and one or more double bonds, such as cyclopentenyl, cyclohexenyl, cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl or similar groups.

[0057] The term "C1-C6 alkoxy" refers to a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, or similar groups.

[0058] The term "halogen" refers to fluorine, chlorine, bromine, or iodine. The term "halogenated" refers to a group substituted with one or more of the same or different halogen atoms, such as trifluoromethyl, pentafluoroethyl, heptafluoroisopropyl, or similar groups.

[0059] The term "alkyl" refers to a group formed by removing one hydrogen atom from an alkane molecule.

[0060] The term "ring" or "cyclic system" refers to carbon rings or heterocycles.

[0061] The terms "heterocyclic group" and "heteroaryl group" refer to atoms forming the heterocycle or heteroaryl ring skeleton where at least one atom is not carbon, but nitrogen, oxygen, or sulfur. Typically, "heterocyclic group" and "heteroaryl group" contain no more than 4 nitrogen atoms, no more than 2 oxygen atoms, and / or no more than 2 sulfur atoms. Unless otherwise specified, the heterocycle can be a saturated or unsaturated ring. Preferred heterocyclic groups include, for example, morpholino, piperidino, piperazino, tetrahydrofurano, tetrahydropyrroleo, tetrahydropyrano, etc. Preferred heteroaryl groups include, for example, thiopheno, furano, pyrroleo, pyridino, thiazolyl, isothiazolo, pyrazolo, pyrimidino, benzofurano, benzopyrroleo, benzothiopheno, indolo, benzimidazolo, quinolino, pyridazino, etc.

[0062] The term "DMSO" refers to dimethyl sulfoxide.

[0063] The term "DMF" refers to N,N-dimethylformamide.

[0064] The term "DAST" refers to diethylaminosulfur trifluoride.

[0065] The term "DCC" refers to dicyclohexylcarbodiimide.

[0066] The term "DMAP" refers to 4-dimethylaminopyridine.

[0067] The term "THF" refers to tetrahydrofuran.

[0068] bactericidal activity of the active substance of the present invention

[0069] The terms "active substance of the present invention" or "active compound of the present invention" refer to compounds with the structure shown in general formula (I) or their optical isomers, cis-trans isomers, or pesticide-acceptable salts thereof. More preferred compounds of the present invention exhibit significant bactericidal activity, a broad bactericidal spectrum, and strong stability.

[0070] The term "pesticide-acceptable salt" means that the anion of the salt is known and acceptable in forming a fungicide-pesticide-acceptable salt. Preferably, the salt is water-soluble. Suitable acid addition salts formed from compounds of formula (I) include salts formed from inorganic acids, such as hydrochlorides, phosphates, sulfates, and nitrates; and salts formed from organic acids, such as carboxylates.

[0071] The compounds involved in this invention have particularly good control effects on rice sheath blight, cucumber gray mold, wheat scab, and rapeseed sclerotinia stem rot.

[0072] Bactericidal compositions containing the active substances of the present invention

[0073] The active substances of the present invention can be prepared into bactericidal compositions using conventional methods. These active compounds can be formulated into conventional preparations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with the active substances, microcapsules in polymers, seed coating compounds, and preparations for use with combustion devices, such as fumigation cylinders, fumigation canisters and fumigation trays, as well as ULV cold mist and warm mist preparations.

[0074] These formulations can be produced using known methods, such as mixing the active compound with a expander, which can be a liquid, liquefied gas, or solid diluent or carrier, and can be any type of surfactant, i.e., emulsifier and / or dispersant and / or foaming agent. For example, when water is used as the expander, organic solvents can also be used as adjuvants.

[0075] Liquid solvents are generally suitable as diluents or carriers, such as: aromatic hydrocarbons, such as xylene, toluene, or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride, or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins, such as mineral oil fractions; alcohols, such as ethanol or ethylene glycol and their ethers and esters; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; or less commonly used polar solvents, such as dimethylformamide, dimethyl sulfoxide, and water.

[0076] A liquefied gas diluent or carrier refers to a liquid that will become a gas at normal temperature and pressure, such as aerosol propellants, halogenated hydrocarbons, and butane, propane, nitrogen, and carbon dioxide.

[0077] Solid carriers can be ground natural minerals such as kaolin, clay, talc, quartz, activated clay, montmorillonite, or diatomaceous earth; and ground synthetic minerals such as highly dispersed silica, alumina, and silicates. Solid carriers for granulation are crushed and graded natural zircon, such as calcite, marble, pumice, sepiolite, dolomite, inorganic and organic coarse powders synthesized into granules, and organic materials such as sawdust, coconut husks, corncobs, and tobacco stalks.

[0078] Nonionic and anionic emulsifiers can be used as emulsifiers and / or foam forming agents. Examples include polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, alkylaryl polyethylene glycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, and albumin hydrolysates. Dispersants include lignin sulfite waste and methylcellulose.

[0079] Binders, such as carboxymethyl cellulose, and natural and synthetic polymers in the form of powders, granules, or emulsions, such as gum arabic, polyvinyl alcohol, and polyvinyl acetate, can be used in the formulation.

[0080] Coloring agents such as inorganic dyes, like iron oxide, cobalt oxide, and Prussian blue; organic dyes, like azo dyes or metallic phthalocyanine dyes; and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, aluminum, and zinc, can be used.

[0081] These active compounds of the present invention can be mixed with other active compounds and exist in their commercial formulations or in dosage forms prepared from these formulations. These other active compounds are insecticides, fungicides, herbicides, growth regulators, etc. Insecticides include, for example, phosphate esters, carbamates, chlorinated hydrocarbons, and substances produced by microorganisms, such as avermectin. Fungicides include methoxyacrylates, amides, triazoles, etc.

[0082] Furthermore, these active compounds of the present invention can also be mixed with synergists in their commercial formulations or in dosage forms prepared from these formulations. These synergists are compounds that enhance the activity of the active compounds. Since the active compounds themselves are active, it is not necessary to add synergists.

[0083] These formulations typically contain 0.001-99.99% by weight, preferably 0.01-99.9% by weight, and more preferably 0.05-90% by weight, of the active compound of the present invention in the total weight of the bactericidal composition. The concentration of the active compound in commercial formulations or drug formulations can vary over a wide range. The concentration of the active compound in drug formulations can range from 0.0000001% to 100% (g / v), preferably between 0.0001% and 1% (g / v).

[0084] Preparation method of the compound of the present invention

[0085] The compounds of general formula (I) of this invention can be prepared by the following method; however, the conditions of this method, such as reactants, solvents, bases, amounts of compounds used, reaction temperatures, and reaction times, are not limited to those explained below. The compounds of this invention can also be conveniently prepared by optionally combining various synthetic methods described in this specification or known in the art, such combinations being readily performed by those skilled in the art.

[0086] The invention is further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. Experimental methods in the following embodiments, unless otherwise specified, are generally performed under conventional conditions, such as those described in Sambrook et al., Molecular Cloning: A Laboratory Manual (New York: Cold Spring Harbor Laboratory Press, 1989), or as recommended by the manufacturer. Unless otherwise stated, percentages and parts are by weight.

[0087] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as are familiar to those skilled in the art. Furthermore, any methods and materials similar to or equivalent to those described herein may be applied to the methods of this invention. The preferred embodiments and materials described herein are for illustrative purposes only.

[0088] Example 1: Preparation of 1-(2,3,5-trichlorophenyl)ethyl 3,3,3-trifluoropropionate

[0089]

[0090] Synthesis of intermediate [1-(2,3,5-trichlorophenyl)ethane-1-ol]:

[0091] In a 100 mL three-necked flask, 5 mmol of 2,3,5-trichlorobenzaldehyde was dissolved in 15 mL of anhydrous THF. The gas was purged three times under argon protection. Then, 0.5 M / 20 mL of methyl magnesium bromide was added dropwise to the reaction mixture under ice bath conditions. After the addition was complete, the mixture was transferred to an oil bath at 60 °C and the reaction was monitored by TLC. The reaction was quenched with saturated ammonium chloride solution, extracted with ethyl acetate (30 mL x 3), dried over anhydrous sodium sulfate, purified by vacuum distillation, and then added to the next step.

[0092] Target product: Preparation of compound I-6 [1-(2,3,5-trichlorophenyl)ethyl 3,3,3-trifluoropropionic acid]

[0093]

[0094] In a 50 mL round-bottom flask, 1 mmol of 1-(2,3,5-trichlorophenyl)ethane-1-ol was dissolved in 10 mL of tetrahydrofuran, followed by the addition of 1.5 mmol of DCC and 0.1 mmol of catalytic DMAP, and then 2 mmol of 3,3,3-trifluoropropionic acid. The mixture was stirred overnight at room temperature, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was filtered through diatomaceous earth, and 10 mL of water was added. The aqueous phase was extracted with ethyl acetate (30 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude product was purified by column chromatography to give 1-(2,3,5-trichlorophenyl)ethyl 3,3,3-trifluoropropionate (85% yield, colorless liquid).

[0095] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ7.44 (d, J = 2.4Hz, 1H), 7.32 (d, J = 2.3Hz, 1H), 6.25 (q, J = 6.5Hz, 1H), 3.26 (q, J = 10.0Hz, 2H), 1.56 (d, J = 6.5Hz, 3H); HRMS (EI) m / z [M] + C 11 H8Cl3F3O2, calculated value: 333.9542, measured value: 333.9547.

[0096] Example 2: Preparation of ethyl 1-(2,3,5-trichlorophenyl)thiazole-4-carboxylate

[0097]

[0098] The synthesis of the target compound was similar to that in Example 1, except that thiazol-4-carboxylic acid was used instead of 3,3,3-trifluoropropionic acid. (74% yield, white solid).

[0099] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ8.89(d,J=1.0Hz,1H),8.31(d,J=1.1Hz,1H),7.46(d,J=1.5Hz ,1H),7.42(s,1H),6.42(q,J=6.4Hz,1H),1.68(d,J=6.5Hz,3H).HRMS(EI)m / z[M]+C 12 H8Cl3NO2S, calculated value: 334.9341, measured value: 334.9338.

[0100] Example 3: Preparation of 1-(2,3,5-trichlorophenyl)prop-2-yn-1-yl 3,3,3-trifluoropropionate

[0101]

[0102] The synthesis of the target compound was similar to that in Example 1, except that...

[0103] The intermediate synthesis was carried out by replacing methyl magnesium bromide with ethynyl magnesium bromide; the oil bath reaction was changed to a room temperature reaction.

[0104] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ7.68(d,J=2.4Hz,1H),7.54(d,J=2.4Hz,1H),6.75(d,J=2.2Hz,1H),3.27(q,J=9.9Hz,2H),2.76(d,J=2.2Hz,1H); HRMS(EI)m / z[M]+C 12 H6Cl3F3O2, calculated value: 343.9385, measured value: 343.9381.

[0105] Example 4: Preparation of 1-(2,3,5-trichlorophenyl)prop-2-yn-1-ylthiazolyl-4-carboxylate

[0106]

[0107] The synthesis of the target compound was similar to that in Example 1, except that...

[0108] The intermediate synthesis was carried out by replacing methyl magnesium bromide with ethynyl magnesium bromide; the oil bath reaction was changed to a room temperature reaction.

[0109] In the second step of the reaction, thiazol-4-carboxylic acid is used instead of 3,3,3-trifluoropropionic acid.

[0110] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ8.87(d,J=2.0Hz,1H),8.33(d,J=2.0Hz,1H),7.81(d,J=2.4Hz,1H) ,7.53(d,J=2.4Hz,1H),6.97(d,J=2.2Hz,1H),2.77(d,J=2.3Hz,1H); HRMS(EI)m / z[M]+C 13 H6Cl3NO2S, calculated value: 344.9185, measured value: 344.9190.

[0111] Example 5: Preparation of 1-(2,3,5-trichlorophenyl)but-2-yn-1-yl 3,3,3-trifluoropropionate

[0112]

[0113] The synthesis of the target compound was similar to that in Example 1, except that...

[0114] The intermediate synthesis was carried out by replacing methyl magnesium bromide with propynyl magnesium bromide; the oil bath reaction was changed to a room temperature reaction.

[0115] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ7.65 (s, 1H), 7.50 (s, 1H), 6.71 (s, 1H), 3.24 (q, J = 10.0Hz, 2H), 1.93 (s, 3H); HRMS (EI) m / z [M] + C 13 H8Cl3F3O2, calculated value: 357.9542, measured value: 357.9546.

[0116] Example 6: Preparation of 1-(2,3,5-trichlorophenyl)but-2-yn-1-ylthiazolyl-4-carboxylate

[0117]

[0118] The synthesis of the target compound was similar to that in Example 1, except that...

[0119] The intermediate synthesis was carried out by replacing methyl magnesium bromide with propynyl magnesium bromide; the oil bath reaction was changed to a room temperature reaction.

[0120] In the second step of the reaction, thiazol-4-carboxylic acid is used instead of 3,3,3-trifluoropropionic acid.

[0121] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ8.86(d,J=2.0Hz,1H),8.30(d,J=2.0Hz,1H),7.77(d,J=2.4Hz,1H) ,7.49(d,J=2.4Hz,1H),6.92(d,J=2.1Hz,1H),1.92(d,J=2.1Hz,3H); HRMS(EI)m / z[M]+C 14 H8Cl3NO2S, calculated value: 358.9341, measured value: 358.9347.

[0122] Example 7: Preparation of cyclopropyl (2,3,5-trichlorophenyl)methyl 3,3,3-trifluoropropionate

[0123]

[0124] The synthesis of the target compound was similar to that in Example 1, except that...

[0125] Cyclopropylmagnesium bromide was used instead of methylmagnesium bromide in the synthesis of intermediates; the oil bath reaction was changed to a room temperature reaction.

[0126] The final test results are as follows: 1H NMR (400MHz, CDCl3) δ7.53 (dd, J=2.0, 1.1Hz, 1H), 7.49 (d, J=2.0Hz, 1H), 5.25 (d, J=1. 0Hz,1H),3.43(q,J=7.5Hz,2H),2.58(s,1H),1.50(d,J=0.9Hz,4H); HRMS(EI)m / z[M]+C 13 H 10 Cl3F3O2, calculated value: 359.9698, measured value: 359.9694.

[0127] Example 8: Preparation of cyclopropyl (2,3,5-trichlorophenyl)methylthiazole-4-carboxylic acid ester

[0128]

[0129] The synthesis of the target compound was similar to that in Example 1, except that...

[0130] Cyclopropylmagnesium bromide was used instead of methylmagnesium bromide in the synthesis of intermediates; the oil bath reaction was changed to a room temperature reaction.

[0131] In the second step of the reaction, thiazol-4-carboxylic acid is used instead of 3,3,3-trifluoropropionic acid.

[0132] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ8.85(s,1H),7.60(s,1H),7.58(dd,J=2.0,0.9Hz,1H),7.51(d,J=2.0H z,1H),5.24(d,J=0.9Hz,1H),2.45(s,1H),1.47(dd,J=29.9,4.9Hz,5H); HRMS(EI)m / z[M]+C 14 H 10 Cl3NO2S, calculated value: 360.9498, measured value: 360.9495.

[0133] Example 9: Preparation of cyano(2,3,5-trichlorophenyl)methyl 3,3,3-trifluoropropionate

[0134]

[0135] Synthesis of intermediate [2-hydroxy-2-(2,3,5-trichlorophenyl)acetonitrile]:

[0136] In a 100 mL three-necked flask, 5 mmol of 2,3,5-trichlorobenzaldehyde was dissolved in 15 mL of anhydrous DMF, followed by the addition of 0.05 mmol of potassium carbonate. The mixture was purged three times under argon protection. Then, 6 mmol of TMSCN was added dropwise at room temperature with stirring. The mixture was monitored by TLC. After the reaction was complete, the solution was quenched with saturated ammonium chloride solution, extracted with ethyl acetate (30 mL x 3), dried over anhydrous sodium sulfate, and distilled under reduced pressure. No further purification was required before proceeding to the next step.

[0137] Target compound I-23 [cyano(2,3,5-trichlorophenyl)methyl 3,3,3-trifluoropropionate]

[0138]

[0139] The synthesis of the target compound was the same as in Example 1;

[0140] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ7.54 (dd, J = 2.0, 1.1Hz, 1H), 7.49 (d, J = 2.0Hz, 1H), 6.60 (d, J = 1.0Hz, 1H), 3.46 (q, J = 10.0Hz, 2H); HRMS (EI) m / z [M] + C 11 H 15 Cl3F3NO2, calculated value: 344.9338, measured value: 344.9342.

[0141] Example 10: Preparation of cyano(2,3,5-trichlorophenyl)methylthiazole-4-carboxylate

[0142]

[0143] The synthesis of the target compound was similar to that in Example 9, except that...

[0144] In the second step of the reaction, thiazol-4-carboxylic acid is used instead of 3,3,3-trifluoropropionic acid.

[0145] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ8.85 (s, 1H), 7.59 (dd, J = 2.0, 0.9Hz, 1H), 7.52 (d, J = 2.0Hz, 1H), 7.39 (s, 1H), 6.79 (d, J = 0.9Hz, 1H); HRMS (EI) m / z [M] + C 14 H 10 Cl3NO2S, calculated value: 345.9137, measured value: 345.9141.

[0146] Example 11: Preparation of cyclobutyl(2,3,5-trichlorophenyl)methyl 3,3,3-trifluoropropionate

[0147]

[0148] The synthesis of the target compound was similar to that in Example 1, except that...

[0149] The intermediate synthesis was carried out by replacing methyl magnesium bromide with cyclobutyl magnesium bromide; the oil bath reaction was changed to a room temperature reaction.

[0150] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ7.53 (dd, J=2.0, 0.9Hz, 1H), 7.50 (d, J=2.0Hz, 1H), 5.28 (d, J=1 .1Hz,1H),3.43(q,J=7.5Hz,2H),2.40(s,1H),1.72–1.23(m,6H); HRMS(EI)m / z[M]+C 14 H 12 Cl3F3O2, calculated value: 373.9855, measured value: 373.9857.

[0151] Example 12: Preparation of cyclobutyl(2,3,5-trichlorophenyl)methylthiazole-4-carboxylic acid ester

[0152]

[0153] The synthesis of the target compound was similar to that in Example 1, except that...

[0154] The intermediate synthesis was carried out by replacing methyl magnesium bromide with cyclobutyl magnesium bromide; the oil bath reaction was changed to a room temperature reaction.

[0155] In the second step of the reaction, thiazol-4-carboxylic acid is used instead of 3,3,3-trifluoropropionic acid.

[0156] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ8.85 (s, 1H), 7.74 (s, 1H), 7.61 (dd, J = 2.0, 1.1Hz, 1H), 7.52 (d, J =2.0Hz,1H),5.27(d,J=1.0Hz,1H),2.40(s,1H),1.72–1.25(m,6H); HRMS(EI)m / z[M]+C 15 H 12 Cl3NO2S, calculated value: 374.9654, measured value: 374.9650.

[0157] Example 13: Preparation of fluoro(2,3,5-trichlorophenyl)methyl 3,3,3-trifluoropropionate

[0158]

[0159] In a 100 mL three-necked flask, 5 mmol of 3,3,3-trifluoropropionic acid was dissolved in 15 mL of anhydrous DCM. The gas was purged three times under argon protection. 10 mmol of DAST was slowly added dropwise under ice bath conditions. After stirring for 20 min, 15 mmol of 2,3,5-trichlorobenzaldehyde (dissolved in 20 mL of DCM) was added. The mixture was then brought to room temperature and stirred, and the reaction was monitored by TLC. After the reaction was complete, it was quenched with saturated sodium bicarbonate solution, extracted with dichloromethane (30 mL x 3), dried over anhydrous sodium sulfate, and distilled under reduced pressure. Column chromatography yielded fluoro(2,3,5-trichlorophenyl)methyl 3,3,3-trifluoropropionic acid ester.

[0160] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ7.62 (dd, J = 2.0, 1.0Hz, 1H), 7.55 (d, J = 2.0Hz, 1H), 6.45 (d, J = 0.9Hz, 1H), 3.43 (q, J = 7.5Hz, 2H); HRMS (EI) m / z [M] + C 10 H5Cl3F4O2, calculated value: 337.9291, measured value: 337.9286.

[0161] Example 14: Preparation of fluoro(2,3,5-trichlorophenyl)methylthiazole-4-carboxylic acid ester

[0162]

[0163] The synthesis of the target compound was similar to that in Example 13, except that...

[0164] Replace 3,3,3-trifluoropropionic acid with thiazole-4-carboxylic acid.

[0165] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ8.85 (s, 1H), 7.64 (dd, J = 2.0, 1.1Hz, 1H), 7.55 (d, J = 2.0Hz, 1H), 7.48 (s, 1H), 7.32 (d, J = 1.1Hz, 1H); HRMS (EI) m / z [M] + C 11 H5Cl3FNO2S, calculated value: 338.9091, measured value: 338.9095.

[0166] Example 15: Preparation of 1-(2,3,5-trichlorophenyl)but-3-yn-2-yl 3,3,3-trifluoropropionate

[0167]

[0168] Synthesis of intermediate a [2-(2,3,5-trichlorophenyl)ethane-1-ol]

[0169] In a 100 mL round-bottom flask, 20 mmol of 2,3,5-trichlorophenylacetic acid was dissolved in 40 mL of anhydrous THF and slowly added to the round-bottom flask containing a LiAlH4 solution (24 mmol, 1.2 equivalents) with a magnetic stir bar under ice bath conditions. The mixture was stirred at 0 °C for one hour. After the reaction was completed, the reaction mixture was quenched by adding cold water until no more hydrogen gas was formed.

[0170] The reaction mixture was extracted with diethyl ether (3 × 20 mL). The combined organic phases were washed with brine (20 mL), dried over anhydrous Na₂SO₄, and concentrated under vacuum to obtain intermediate a for the next step without further purification.

[0171] Synthesis of intermediate b [2-(2,3,5-trichlorophenyl)acetaldehyde]

[0172] DCM (50 mL) and DMP (24 mmol, 1.2 equivalence) were added to intermediate a (20 mmol, 1.0 equivalence). The reaction mixture was stirred at room temperature for 2 hours. After completion, the reaction mixture was quenched by adding saturated sodium thiosulfate (50 mL) and stirred until the organic phase became clear (approximately 30 minutes). The organic phase was washed with brine (20 mL), purified with anhydrous Na₂SO₄, dried, and concentrated under vacuum to obtain the residue, which was used to give intermediate b by rapid column chromatography on silica gel.

[0173] Synthesis of intermediate c[1-(2,3,5-trichlorophenyl)but-3-yn-2-ol]

[0174] The synthesis of intermediate c is similar to that in Example 3, except that 2,3,5-trichlorophenylacetaldehyde is used instead of 2,3,5-trichlorobenzaldehyde.

[0175] Target compound I-196 [1-(2,3,5-trichlorophenyl)but-3-yn-2-yl 3,3,3-trifluoropropionate]

[0176]

[0177] The synthesis of the target compound was similar to that in Example 1, except that...

[0178] 1-(2,3,5-trichlorophenyl)but-3-yne-2-ol replaces 1-(2,3,5-trichlorophenyl)ethane-1-ol.

[0179] The final test results are as follows: 1 H NMR(400MHz, CDCl3) δ7.52(d,J=1.8Hz,1H),7.38(dt,J=2.0,1.0Hz,1H),5.17(s ,1H),3.56(q,J=10.0Hz,2H),3.29(s,1H),3.24–2.98(m,2H); HRMS(EI)m / z[M]+C 10 H5Cl3F3O2, calculated value: 357.9542, measured value: 357.9546.

[0180] Example 16: Preparation of 1-(2,3,5-trichlorophenyl)but-3-yn-2-ylthiazolyl-4-carboxylate

[0181]

[0182] The synthesis of the target compound was similar to that in Example 15, except that...

[0183] In the final step of the reaction, thiazol-4-carboxylic acid is used instead of 3,3,3-trifluoropropionic acid.

[0184] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ8.85 (s, 1H), 7.52 (d, J = 1.8Hz, 1H), 7.39 (s, 1H), 7.37–7. 35(m,1H),5.15(s,1H),3.45(d,J=1.0Hz,2H),3.28(s,1H); HRMS(EI)m / z[M]+C 14 H8Cl3NO2S, calculated value: 358.9341, measured value: 358.9346.

[0185] Example 17: Preparation of 1-(3,5-dichloro-2-methylphenyl)prop-2-yn-1-yl 3,3,3-trifluoropropionate

[0186]

[0187] Synthesis of intermediate a [3,5-dichloro-2-methylbenzaldehyde]

[0188] In a 100 mL three-necked flask, under nitrogen protection at -78 °C, 20 mmol of n-butyllithium (n-hexane solution) was slowly added dropwise to a 10 mmol solution of 2,3,5-trichlorobenzaldehyde in tetrahydrofuran. The reaction was stirred at -78 °C for one hour, followed by the addition of 15 mmol of DMF. The reaction was continued for another hour. After completion, the reaction was quenched with saturated ammonium chloride solution, and the reaction mixture was extracted with ethyl acetate (3 × 20 mL). The combined organic phases were dried over anhydrous sodium sulfate and concentrated under vacuum to obtain an intermediate for the next step without further purification.

[0189] The synthesis of intermediate b [1-(3,5-dichloro-2-methylphenyl)prop-2-yn-1-ol] is similar to that in Example 1, except that;

[0190] Magnesium methyl bromide was replaced with acetylated magnesium bromide; the oil bath reaction was changed to a room temperature reaction.

[0191] Compound I-214 [1-(2,3,5-trichlorophenyl)but-3-yn-2-yl 3,3,3-trifluoropropionate]

[0192]

[0193] The synthesis of the target compound was similar to that in Example 1, except that...

[0194] 1-(3,5-Dichloro-2-methylphenyl)prop-2-yn-1-ol replaces 1-(2,3,5-trichlorophenyl)ethane-1-ol.

[0195] The final test results are as follows: 1 H NMR (400MHz, CDCl3) δ7.48 (d, J=2.0Hz, 1H), 7.26 (dd, J=2.0, 1.1Hz, 1H), 7.19 (d, J=0.9Hz,1H),3.46q,J=10.0Hz,2H),3.14(s,1H),2.53(s,2H); HRMS(EI)m / z[M]+C 13 H9Cl2F3O2, calculated value: 323.9932, measured value: 323.9936.

[0196] Example 18: Preparation of 1-(3,5-dichloro-2-methylphenyl)prop-2-yn-1-ylthiazolyl-4-carboxylate

[0197]

[0198] The synthesis of the target compound was similar to that in Example 19, except that...

[0199] In the final step of the reaction, thiazol-4-carboxylic acid is used instead of 3,3,3-trifluoropropionic acid.

[0200] The final test results are as follows: 1 H NMR(400MHz, CDCl3)δ8.85(s,1H),7.52(s,1H),7.41(d,J=2.0Hz,1H),7.29(s,0H),6.72(d,J=0.9Hz,1H),3.04(s,1H),2.53(s,3H); HRMS(EI)m / z[M]+C 14 H9Cl2NO2S, calculated value: 324.9731, measured value: 324.9735.

[0201] The other compounds in Table 1 were synthesized using the synthetic methods of Examples 1-18 or similar organic reactions.

[0202] Example 19: Bioactivity experiment of the compounds of the present invention

[0203] (1) Activation culture of four tested plant pathogenic fungi

[0204] RS (Rhizoctonia solani); BC (Botrytis cinerea); Fg (Fusarium Gibberella); SS (Sclerotinia sclerotiorum).

[0205] The slant culture of rice sheath blight pathogen was picked up with an inoculation needle and inoculated into potato dextrose agar (PDA) plates for activation using the streak method. The plates were then incubated at (28±1)℃ for 48 h.

[0206] The slant culture of cucumber gray mold was picked up with an inoculation needle and inoculated into potato dextrose agar (PDA) plates for activation using the streak method. The plates were then incubated at (25±1)℃ for 72 h.

[0207] The slant culture of wheat scab was picked up with an inoculation needle and inoculated into potato dextrose agar (PDA) plates for activation using the streak method. The plates were then incubated at (25±1)℃ for 96 h.

[0208] The slant culture of Sclerotinia sclerotiorum var. sclerotiorum was picked up with an inoculation needle and inoculated into potato dextrose agar (PDA) plates for activation. The plates were then incubated at (28±1)℃ for 48 h.

[0209] (2) Determination of antibacterial activity by mycelial growth rate method

[0210] Weigh 1 mg of the compound and dissolve it in 1 mL of dimethyl sulfoxide (DMSO) to prepare a 1000 mg / L stock solution. Add 0.5 mL of the drug-containing DMSO solution and 0.5 mL of 0.1% Tween 80 aqueous solution to 49 mL of PDA medium. Dilute the stock solution 100 times to a final concentration of 10 mg / L. The blank control consisted of 0.5 mL DMSO + 0.5 mL 0.1% Tween 80 aqueous solution. Shake the drug-containing PDA medium well and pour it evenly into three sterile petri dishes with a diameter of 9 cm. After the PDA solidifies, select the fungus to be tested, use a punch to prepare mycelial discs with a diameter of 5 mm, and then inoculate them into the drug-containing medium. Seal the petri dishes to prevent contamination, label them, and place them in a temperature-controlled, light-based incubator for 48-96 hours.

[0211] The colony diameter was determined using the cross-cross method, and the inhibition rate was calculated using the following formula:

[0212]

[0213] The antibacterial results of compound (I) at 10 mg / L against four plant fungi are shown in Table 1.

[0214] Table 2 shows the antibacterial activity of compounds of formula (I).

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223] All documents mentioned in this invention are incorporated herein by reference as if each document were individually incorporated by reference. Furthermore, it should be understood that after reading the foregoing teachings of this invention, those skilled in the art can make various alterations or modifications to this invention, and these equivalent forms also fall within the scope defined by the appended claims.

Claims

1. A methylene ester-bridged compound, and its optical isomers, cis-trans isomers, or pesticide-acceptable salts thereof, characterized in that, The compound has the structure shown in formula (I): Wherein, A is independently selected from the group consisting of: phenyl, -(C1-C8 alkylene)phenyl, -N=CH-phenyl; wherein one or more hydrogen atoms on A are optionally substituted by Ra, wherein Ra is selected from the group consisting of: halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C8 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 thioalkyl; T is independently: halogen, hydroxyl, nitro, amino, cyano, or a substituted or unsubstituted group selected from the group consisting of: C1-C8 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 alkenoxy, C2-C6 alkynoxy, C1-C6 alkoxy, C3-C6 cycloalkoxy, C5-C7 cycloalkenyl, C3-C 10 Cycloalkyl, 4-8 membered heterocyclic, C6-C 10 Aryl, 5-8 membered aromatic heterocyclic, -(C1-C8 alkylene)(C6-C 10 aryl), -(C6-C 10 aryl)-O-(C6-C 10 aryl), -(C6-C 10 aryl)-(C6-C 10 aryl), -(C1-C8 alkylene)(5-10 heteroaryl), -OC(=O)(C6-C 10 aryl), -OC (=O)(C6-C 10 Aryl)(C2-C6 alkenyl), -OC(=O)(C1-C8 alkylene)(C6-C 10 Aryl), -OC(=O)(C1-C8 alkylene)phenyl(C2-C6 alkenyl), -(C1-C8 alkylene)(C3-C6 cycloalkyl), -(C1-C8 alkylene)(4-10 heterocyclic), -(C1-C8 alkylene)NHC(=O)(4-10 heteroaryl); W is independently: cyano, substituted or unsubstituted groups selected from the group consisting of C1-C. 10 Alkyl, C2-C6 alkenyl, C2-C6 ynyl, C6-C 10 Aryl, 5-8 membered heteroaryl, 4-8 membered heterocyclic, C3-C 10 Cycloalkyl, -(C1-C8 alkylene)(C3-C 10 cycloalkyl), -(C1-C8 alkylene)(C6-C 10 aryl), -(C1-C8 alkylene)(4-10 heteroaryl), -(C1-C8 alkylene)(4-8 heterocyclic), -O(C1-C 10 Alkyl), -O (C3-C) 10 cycloalkyl), -O (C6-C) 10 aryl), -O (4-10 membered heteroaryl), -O (4-8 membered heterocyclic), -NH (C1-C 10 Alkyl), -NH (C3-C) 10 cycloalkyl), -NH (C6-C 10 Aryl), -NH (4-10 membered heteroaryl), -NH (4-8 membered heterocyclic); Unless otherwise specified, substitution means that one or more hydrogen atoms on a group are substituted by a substituent selected from the group consisting of: deuterium, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 alkoxy, halo-C1-C4 alkyl, and halo-C1-C4 alkoxy.

2. The compound according to claim 1, characterized in that, The compound has the structures shown in formulas (IA) and (IB): Wherein, R1 is selected from the group consisting of: halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C8 alkyl; m and n are each independently an integer between 0 and 5; The remaining substituents are as described in claim 1.

3. The compound according to claim 1, characterized in that, Each of the following groups, T, is independently: halogen, hydroxyl, nitro, amino, cyano, C1-C4 alkyl, halo-C1-C4 alkyl, C2-C4 alkenyl, halo-C2-C4 alkenyl, C2-C4 alkynyl, halo-C2-C4 alkynyl, C2-C4 alkenoxy, halo-C2-C4 alkenoxy, C2-C4 alkynoxy, C1-C4 alkoxy, or substituted or unsubstituted of the following groups: C3-C7 cycloalkyl, five-membered heterocyclic, phenyl, 5-8-membered aromatic heterocyclic, biphenyl, naphthyl.

4. The compound according to claim 1, characterized in that, Each of the following T groups is independently: halogen, hydroxyl, nitro, amino, cyano, methyl, ethyl, propyl, isopropyl, ethynyl, propynyl, butynyl, ethoxy, propoxy, isopropoxy, propynylated, fluoroethynyl, bromoethynyl, chloroethynyl, fluoropropynyl, bromopropynyl, chloropropynyl, fluorobutynyl, bromobutynyl, chlorobutynyl, trifluoromethyl, difluoromethyl, Where X is selected from: F, Cl, Br, I, CF3, OCF3, OCH3; o and p are selected from 0, 1, 2, 3, 4, and 5.

5. The compound according to claim 1, characterized in that, Each of the W groups is independently: cyano, C1-C4 alkyl, halo-C1-C4 alkyl, or substituted or unsubstituted of the following groups: C3-C7 cycloalkyl, phenyl, 5-8 membered aromatic heterocyclic group.

6. The compound according to claim 1, characterized in that, Each of the following groups of W is independently: cyano, -CF3, -CH2CF3, -CH2CH2CF3, Y is selected from: F, Cl, Br, I; q is selected from 0, 1, 2, 3, 4, 5.

7. The compound according to claim 1, characterized in that, The compounds are selected from the following table:

8. A pesticide composition, characterized in that, Comprising: (a) the compound of any one of claims 1-7, its optical isomer, cis-trans isomer, or a pesticide-acceptable salt thereof, or a combination thereof; and Optional (b) pesticide-acceptable carriers and / or excipients.

9. The use of the compound according to any one of claims 1-7, its optical isomer, cis-trans isomer, or a pesticide composition according to claim 8, characterized in that, Used in the preparation of bactericides.

10. A method for preventing and controlling plant pathogens, characterized in that, This includes applying to the environment, soil, or plants requiring control any of the compounds described in claims 1-7, their optical isomers, cis-trans isomers, or pesticide compositions as described in claim 8.

Images