A carbonyl compound, its preparation method and use

Through the synthesis and application of carbonyl-containing compounds, the problem of resistance to existing amide bactericides was solved, and high-efficiency, low-toxicity, and no interaction resistance were developed to prevent and treat a variety of plant bacteria, achieving significant antibacterial effects and stability.

CN113024379BActive Publication Date: 2025-05-27EAST CHINA UNIV OF SCI & TECH
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Patent Information

Application Number
CN202110272320.2
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2021-03-12
Publication Date
2025-05-27
Estimated Expiration
2041-03-12

AI Technical Summary

Technical Problem

Existing amide fungicides become resistant after long-term use, resulting in a reduced effect in preventing and treating plant bacteria. It is necessary to develop highly efficient, low-toxic and non-interactive resistance fungicides.

Method used

Carbonyl-containing compounds are used as active ingredients of the fungicide to synthesize a series of carbonyl compounds with multiple antibacterial activities to prevent and treat a variety of plant diseases including cucumber downy mildew, cucumber anthrax, wheat powdery mildew, corn rust, rice vein blight, cucumber grey mold, etc.

Benefits of technology

These carbonyl-containing compounds show significant antibacterial activity, can effectively inhibit a variety of plant bacteria, and are highly stable and have low cost, making them suitable for agricultural production.

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Abstract

The present invention discloses a carbonyl-containing compound, its preparation method and uses. The structure of the compound is as described in General Formula I, and the definitions of each substituent are as described in the specification and claims. The compounds of the present invention have broad-spectrum bactericidal activity against various plant fungal diseases, and can be used alone or in combination with other agents for the control of various plant fungal diseases, especially having excellent control effects on cucumber downy mildew, cucumber anthracnose, wheat powdery mildew, corn rust, rice sheath blight, and cucumber gray mold.
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Description

Technical Field

[0001] The present invention relates to carbonyl-containing compounds and their preparation methods and uses. Background Art

[0002] Plant pathogens cause great harm to the growth of plants, causing huge losses to agriculture every year. To prevent the occurrence of plant diseases and reduce the losses caused by them, a large number of antibacterial and bactericidal active compounds have been reported and applied. Due to factors such as drug resistance, the research and development of new fungicides has always been a hot topic of concern for pesticide companies and researchers.

[0003] Amide compounds have been used as fungicides for decades, and more than 30 varieties have been commercialized so far. Most of these fungicides have good control effects on oomycete diseases. Due to long-term use, these compounds have now begun to develop drug resistance, and there is a need to develop fungicides with high efficiency, low toxicity, and no cross-resistance. Summary of the Invention

[0004] The object of the present invention is to provide carbonyl-containing compounds for controlling plant pathogens.

[0005] In a first aspect of the present invention, there is provided a compound having the structure shown in general formula (I), its optical isomers, cis-trans isomers or its agriculturally acceptable salts,

[0006]

[0007] wherein, T is H, cyano or a substituted or unsubstituted group selected from the following groups: C 1 -C 8 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyl, C 2 -C 6 alkynyloxy, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C 5 -C 7 cycloalkenyl, 4-8 membered heterocyclic group, C 6 -C 10 aryl, -OC(=O)(C 6 -C 10 aryl), -OC(=O)(C 6 -C 10 aryl)(C2 -C 6 alkenyl), -OC(=O)(C 1 -C 8 alkylene)(C 6 -C 10 aryl), -OC(=O)(C 1 -C 8 alkylene)phenyl(C 2 -C 6 alkenyl), 4-8 membered heteroaryl, -(C 1 -C 8 alkylene)(4-10 membered heteroaryl), -(C 1 -C 8 alkylene)(C 6 -C 10 aryl), -(C 1 -C 8 alkylene)(C 3 -C 6 cycloalkyl), -(C 1 -C 8 alkylene)(4-10 membered heterocyclic group), -(C 1 -C 8 alkylene)NHC(=O)(4-10 membered heteroaryl), -NR a R b ; wherein R a , R b are each independently selected from H, C 1 -C 8 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 8 haloalkyl, C 6 -C 10 aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group, -C(=O)C 1 -C 8 alkyl, -C(=O)C 3 -C 6 cycloalkyl, -C(=O)C 1 -C 8 haloalkyl, -C(=O)C 6 -C 10 aryl, -C(=O)4-8 membered heteroaryl, -C(=O)4-8 membered heterocyclic group; wherein the substitution means being substituted by one or more groups selected from the group consisting of: cyano, hydroxy, oxo(=O), C 1 -C 8 alkyl, halogen (fluorine, chlorine, bromine), C 1 -C 8 haloalkyl, -C(=O)NH(C1 -C 8 alkyl), C 3 -C 6 cycloalkyl, C 1 -C 8 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, nitro, C 2 -C 6 alkynyl, C 6 -C 10 aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group, -C(=O)O(C 1 -C 8 alkyl) or C 1 -C 6 thioalkyl.

[0008] In another preferred embodiment, T is H, or is a substituted or unsubstituted group selected from the group consisting of: C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, 5-7 membered heterocyclic group, phenyl, 5-7 membered heteroaryl, -(C 1 -C 8 alkylene)(4-10 membered heteroaryl), -(C 1 -C 8 alkylene)(C 6 -C 10 aryl), -(C 1 -C 8 alkylene)(C 3 -C 6 cycloalkyl), -(C 1 -C 8 alkylene)(4-10 membered heterocyclic group), -(C 1 -C 8 alkylene)NHC(=O)(4-10 membered heteroaryl), -NR a R b ; wherein R a 、R b are each independently selected from H, C 1 -C 8 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 8 haloalkyl, C 6 -C 10Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group, -C(=O)C 1 -C 8 Alkyl, -C(=O)C 3 -C 6 Cycloalkyl, -C(=O)C 1 -C 8 Halogenated alkyl, -C(=O)C 6 -C 10 Aryl, -C(=O)4-8 membered heteroaryl, -C(=O)4-8 membered heterocyclic group; wherein the substitution means being substituted by one or more groups selected from the group consisting of: cyano, hydroxy, oxo(=O), C 1 -C 8 Alkyl, fluorine, chlorine, bromine, C 1 -C 6 Halogenated alkyl, -C(=O)NH(C 1 -C 8 Alkyl), C 3 -C 6 Cycloalkyl, C 1 -C 4 Alkoxy, C 1 -C 6 Halogenated alkoxy, C 2 -C 6 Alkenyl, nitro, C 2 -C 6 Alkynyl, phenyl, 4-8 membered heteroaryl, 5-7 membered heterocyclic group, -C(=O)O(C 1 -C 8 Alkyl) or C 1 -C 6 Thioalkyl.

[0009] In another preferred embodiment, T is H, or is a substituted or unsubstituted group selected from the group consisting of: C 1 -C 4 Alkyl, phenyl, C 2 -C 6 Alkenyl, C 3 -C 6 Cycloalkyl, 5-6 membered heterocyclic group; wherein the substitution means being substituted by one or more groups selected from the group consisting of: fluorine, chlorine, bromine, cyano, C 1 -C 4 Alkyl, C 1 -C 4 Halogenated alkyl, C 1 -C 4 Alkoxy, 5-6 membered heterocyclic group, phenyl.

[0010] In another preferred embodiment, T is any of the groups listed in Table 1.

[0011] Z is O or NR2 ; wherein, R 2 is hydrogen, or a substituted or unsubstituted group selected from the group consisting of: C 1 -C 8 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyl, C 2 -C 6 alkynyloxy, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C 5 -C 7 cycloalkenyl, 4- to 8-membered heterocyclic group, C 6 -C 10 aryl, -(C 1 -C 8 alkylene)(4- to 10-membered heteroaryl), -(C 1 -C 8 alkylene)(C 6 -C 10 aryl), -(C 1 -C 8 alkylene)(C 3 -C 6 cycloalkyl), -(C 1 -C 8 alkylene)(4- to 10-membered heterocyclic group), -(C 1 -C 8 alkylene)NHC(=O)(4- to 10-membered heteroaryl); wherein the substitution means being substituted by one or more groups selected from the group consisting of: halogen (fluorine, chlorine, bromine), cyano, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, nitro, hydroxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 aryl, 4- to 8-membered heteroaryl, 4- to 8-membered heterocyclic group, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C1 -C 6 Thioalkyl group

[0012] In another preferred example, Z is O or NR 2 ; wherein, R 2 is hydrogen, or a substituted or unsubstituted group selected from the group consisting of: -(C 1 -C 4 alkylene)(5-7 membered heteroaryl), -(C 1 -C 4 alkylene)(C 6 -C 10 aryl), -(C 1 -C 4 alkylene)(C 3 -C 6 cycloalkyl), -(C 1 -C 4 alkylene)(4-10 membered heterocyclic group), -(C 1 -C 4 alkylene)NHC(=O)(4-10 membered heteroaryl); wherein the substitution means being substituted by one or more groups selected from the group consisting of: halogen (fluorine, chlorine, bromine), cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, nitro, hydroxy, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 6 -C 10 aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 thioalkyl group

[0013] In another preferred example, Z is O or NH

[0014] R 1 is a substituted or unsubstituted group selected from the group consisting of: C 1 -C 10 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10Aryl, 4- to 8-membered heteroaryl, 4- to 8-membered heterocyclic group, C 3 -C 10 Cycloalkyl, -(C 1 -C 8 Alkylene)(C 3 -C 10 Cycloalkyl), -(C 1 -C 8 Alkylene)(C 6 -C 10 Aryl), -(C 1 -C 8 Alkylene)(4- to 10-membered heteroaryl), -(C 1 -C 8 Alkylene)(4- to 8-membered heterocyclic group); wherein the substitution means being substituted by one or more groups selected from the group consisting of: cyano, oxo(=O), C 1 -C 8 Alkyl, halogen (fluorine, chlorine, bromine), C 1 -C 8 Halogenated alkyl, halogenated 4- to 8-membered heteroaryl, -C(=O)NH(C 1 -C 8 Alkyl), C 3 -C 6 Cycloalkyl, C 1 -C 8 Alkoxy, C 1 -C 6 Halogenated alkoxy, C 2 -C 6 Alkenyl, nitro, hydroxy, C 2 -C 6 Alkynyl, C 6 -C 10 Aryl, 4- to 8-membered heteroaryl, 4- to 8-membered heterocyclic group, -O(C 6 -C 10 Aryl) or C 1 -C 6 Thioalkyl.

[0015] In another preferred embodiment, R 1 is a group selected from the group consisting of substituted or unsubstituted: C 1 -C 6 Alkyl, C 2 -C 4 Alkenyl, C 2 -C 4 Alkynyl, phenyl, 5- to 7-membered heteroaryl, 5- to 7-membered heterocyclic group, C 3 -C 8 Cycloalkyl, -(C 1 -C 6 Alkylene)(C 3 -C8 cycloalkyl), -(C 1 -C 6 alkylene)phenyl, -(C 1 -C 6 alkylene)(4-10 membered heteroaryl), -(C 1 -C 6 alkylene)(5-7 membered heterocyclic group); wherein said substitution means being substituted by one or more groups selected from the group consisting of: cyano, oxo(=O), C 1 -C 6 alkyl, fluorine, chlorine, bromine, C 1 -C 4 haloalkyl, halo 5-7 membered heteroaryl, -C(=O)NH(C 1 -C 6 alkyl), C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, nitro, hydroxy, C 2 -C 6 alkynyl, phenyl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group, -O-phenyl or C 1 -C 6 thioalkyl.

[0016] In another preferred embodiment, R 1 is C 3 -C 8 cycloalkyl, -(C 1 -C 8 alkylene)(C 3 -C 8 cycloalkyl), -(C 1 -C 8 alkylene)(C 6 -C 10 aryl), -(C 1 -C 8 alkylene)(4-10 membered heteroaryl), -(C 1 -C 8 alkylene)(4-8 membered heterocyclic group); wherein said substitution means being substituted by one or more groups selected from the group consisting of: cyano, oxo(=O), C 1 -C 8 alkyl, halogen (fluorine, chlorine, bromine), C 1 -C 8 haloalkyl, halo 4-8 membered heteroaryl, -C(=O)NH(C 1 -C 8(alkyl), C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, nitro, hydroxy, C 2 -C 6 alkynyl, phenyl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group, -O-phenyl) or C 1 -C 6 thioalkyl.

[0017] In another preferred embodiment, R 1 is -(C 1 -C 8 alkylene)(C 6 -C 10 aryl); wherein said substitution means being substituted by one or more groups selected from the group consisting of cyano, oxo(=O), C 1 -C 8 alkyl, halogen (fluorine, chlorine, bromine), C 1 -C 8 haloalkyl, halo 4-8 membered heteroaryl, -C(=O)NH(C 1 -C 8 alkyl), C 3 -C 6 cycloalkyl, C 1 -C 8 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyl, nitro, hydroxy, C 2 -C 6 alkynyl, C 6 -C 10 aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group, -O(C 6 -C 10 aryl) or C 1 -C 6 thioalkyl.

[0018] In another preferred embodiment, R 1 is C 2 -C 4 alkenyl, phenyl, C 3 -C 8 cycloalkyl, -(C 1 -C 4 alkylene)(C 3 -C 8 cycloalkyl), -(C1 -C 4 alkylene)phenyl, -(C 1 -C 4 alkylene)(4-10 membered heteroaryl), -(C 1 -C 4 alkylene)(5-7 membered heterocyclic group); wherein said substitution means being substituted by one or more groups selected from the group consisting of: cyano, oxo(=O), C 1 -C 4 alkyl, fluorine, chlorine, bromine, C 1 -C 4 haloalkyl, halo 5-7 membered heteroaryl, -C(=O)NH(C 1 -C 4 alkyl), C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyl, nitro, hydroxy, C 2 -C 6 alkynyl, phenyl, 5-7 membered heteroaryl, 5-7 membered heterocyclic group, -O-phenyl or C 1 -C 6 thioalkyl.

[0019] In another preferred embodiment, R 1 is any one of the groups listed in Table 1.

[0020] In another preferred embodiment, the compound has the following structure: R 1 -OCO(C 1 -C 6 alkyl), preferably R 1 -OCO(C 1 -C 4 alkyl), wherein the above alkyl is optionally substituted by 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 groups selected from the group consisting of: cyano, hydroxy, oxo(=O), C 1 -C 4 alkyl, fluorine, chlorine, bromine, C 1 -C 4 haloalkyl (preferably trifluoromethyl), -C(=O)NH(C 1 -C 4 alkyl), C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4Halogenated alkoxy (preferably trifluoromethoxy), C 2 -C 4 -alkenyl, nitro, C 2 -C 4 -alkynyl, phenyl, 5- to 7-membered heteroaryl, 5- to 7-membered heterocyclic group.

[0021] In another preferred example, the compound has the following structure: R 1 -OCOPh, wherein the above Ph is optionally substituted by 1, 2, 3, 4 or 5 groups selected from the group consisting of: cyano, hydroxy, oxo (=O), C 1 -C 4 -alkyl, fluorine, chlorine, bromine, C 1 -C 4 -haloalkyl (preferably trifluoromethyl), -C(=O)NH(C 1 -C 4 -alkyl), C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenated alkoxy (preferably trifluoromethoxy), C 2 -C 4 -alkenyl, nitro, C 2 -C 4 -alkynyl, phenyl, 5- to 7-membered heteroaryl, 5- to 7-membered heterocyclic group.

[0022] In another preferred example, the compound has the following structure: Ph-(C 1 -C 4 -alkylene)OCO(C 1 -C 6 -alkyl), preferably Ph-(C 1 -C 4 -alkylene)OCO(C 1 -C 4 -alkyl), wherein the above alkyl is optionally substituted by 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 groups selected from the group consisting of: cyano, hydroxy, oxo (=O), C 1 -C 4 -alkyl, fluorine, chlorine, bromine, C 1 -C 4 -haloalkyl (preferably trifluoromethyl), -C(=O)NH(C 1 -C 4 -alkyl), C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4Halogenated alkoxy groups (preferably trifluoromethoxy), C 2 -C 4 alkenyl, nitro, C 2 -C 4 alkynyl, phenyl, -O-phenyl, 5- to 7-membered heteroaryl, 5- to 7-membered heterocyclic group.

[0023] In another preferred example, the compound is any compound in Table 1.

[0024] In a second aspect of the present invention, there is provided an agricultural composition comprising:

[0025] (a) 0.001-99.99 wt% of the compound described in the first aspect of the present invention, its optical isomers, cis-trans isomers, or its pharmaceutically acceptable salts, or a combination thereof; and

[0026] (b) a pesticidally acceptable carrier and / or excipient.

[0027] In another preferred example, component (a) accounts for 0.001-99.99 wt% of the total weight of the pharmaceutical composition; preferably 0.01-99.9 wt%; more preferably 0.05-90 wt%.

[0028] In the present invention, there is provided a drug with a carbonyl compound as the active ingredient. When needed, one or more carriers acceptable in pesticide formulations can also be added to the drug. The carriers include conventional diluents, excipients, fillers, binders, wetting agents, absorption promoters, surfactants, lubricants, stabilizers, defoaming agents, diatomaceous earth, etc. in pesticide formulations. The dosage forms of the prepared drugs are also diverse and can be powders, emulsions, aqueous solutions, granules, corrosion inhibitors, effervescent tablets, etc.

[0029] In another aspect of the present invention, there is provided the use of the compound described in the first aspect, its optical isomers, cis-trans isomers or its pesticidally acceptable salts or the pesticidal composition described in the second aspect for preparing a bactericide.

[0030] In another preferred example, the bactericide controls the following diseases: cucumber downy mildew, cucumber gray mold, corn rust, rice sheath blight, wheat powdery mildew.

[0031] In another aspect of the present invention, there is provided a method for controlling plant pathogens, including applying to plants the compound described in the first aspect, its optical isomers, cis-trans isomers or its pesticidally acceptable salts or the pesticidal composition described in the second aspect.

[0032] The present invention synthesizes a carbonyl compound, and the preparation method is simple and easy to implement, the operation is simple, the product purification is easy, the cost is low, and the stability is improved.

[0033] The carbonyl compound contained in the present invention has been proven to have obvious antibacterial activity through tests and is used for preventing and controlling diseases of crops, fruit trees, Chinese herbal medicines and flowers.

[0034] The substantial features of the present invention can be embodied in the following embodiments, but it should not be regarded as any limitation to the present invention. Specific embodiments

[0035] The inventors of the present application have conducted extensive and in-depth research and developed a series of carbonyl compounds with multiple antibacterial activities. They not only have obvious inhibitory effects on cucumber downy mildew and cucumber anthracnose, but also have good inhibitory activities on wheat powdery mildew, corn rust, rice sheath blight and cucumber gray mold, and can be used as pesticides in agricultural production.

[0036] Group definition

[0037] The term "C 1 -C 8 alkyl" refers to a straight-chain or branched-chain 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.

[0038] The term "C 2 -C 6 alkenyl" refers to a straight-chain or branched-chain alkenyl group having 2 to 6 carbon atoms, such as vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl or similar groups.

[0039] The term "C 2 -C 6 alkynyl" refers to a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms, such as ethynyl, propynyl or similar groups.

[0040] The term "C 3 -C 6 cycloalkyl" refers to a cyclic alkyl group having 3 to 7 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or similar groups.

[0041] The term "C 5 -C 7 cycloalkenyl" refers to a cyclic alkenyl group having 5 to 7 carbon atoms and one or more double bonds, such as cyclopentenyl, cyclohexenyl, cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl or similar groups.

[0042] The term "C 1 -C 6"Alkoxy" refers to a straight-chain or branched alkoxy group having 1-6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy or similar groups.

[0043] The term "halogen" refers to fluorine, chlorine, bromine or iodine. The term "halogenated" refers to a group substituted by one or more of the above halogen atoms which may be the same or different, such as trifluoromethyl, pentafluoroethyl, heptafluoroisopropyl or similar groups.

[0044] The term "alkyl" refers to a group formed by removing one hydrogen atom from an alkane molecule.

[0045] The term "ring" or "ring system" refers to a carbocyclic or heterocyclic ring.

[0046] The terms "heterocyclic group" and "heteroaryl" mean that at least one of the atoms forming the heterocyclic or heteroaromatic ring skeleton is not carbon, but nitrogen, oxygen or sulfur. Generally, "heterocyclic group" and "heteroaryl" contain no more than 4 (such as 1, 2 or 3) nitrogens, no more than 2 (such as 1 or 2) oxygens and / or no more than 2 (such as 1 or 2) sulfurs. Unless otherwise specified, the heterocyclic ring can be a saturated, partially unsaturated or fully unsaturated ring. For example, preferred heterocyclic groups are rings containing 1, 2, 3 or 4 heteroatoms selected from nitrogen, oxygen or sulfur. For example, the heterocyclic group is morpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydropyranyl, etc. For example, preferred heteroaryl groups are rings containing 1, 2, 3 or 4 heteroatoms selected from nitrogen, oxygen or sulfur. For example, the heteroaryl group is pyridyl, thiazolyl, isothiazolyl, thienyl, furyl, pyrrolyl, pyrazolyl, pyrimidinyl, benzopyrrolyl, benzofuranyl, benzothienyl, indolyl, benzimidazolyl, quinolinyl, pyridazinyl, etc.

[0047] The term "DCC" refers to dicyclohexylcarbodiimide. The term "DMAP" refers to 4-dimethylaminopyridine.

[0048] The term "THF" refers to tetrahydrofuran.

[0049] The bactericidal activity of the active substance of the present invention

[0050] The term "active substance of the present invention" or "active compound of the present invention" refers to a compound having the structure shown in general formula (I) or a pesticidally acceptable salt. Its heterocyclic structure containing N and O has significant bactericidal activity, a broad bactericidal spectrum and strong stability.

[0051] The term "pesticidally acceptable salt" means that the anion of the salt is known and acceptable when forming a pharmaceutically acceptable salt of the fungicide. Preferably, the salt is water-soluble. Suitably, the acid addition salts formed by the compounds of formula (I) include salts formed by inorganic acids, such as hydrochlorides, phosphates, sulfates, nitrates; and include salts formed by organic acids, such as carboxylates.

[0052] The compounds involved in the present invention have good control effects especially on cucumber downy mildew, cucumber anthracnose, wheat powdery mildew, corn rust, rice sheath blight, and cucumber gray mold.

[0053] The fungicide composition containing the active substance of the present invention

[0054] The active substances of the present invention can be prepared into fungicidal compositions by conventional methods. These active compounds can be made 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, coating compounds for seeds, and preparations used with combustion devices, such as smoking cartridges, smoking cans, and smoking trays, as well as ULV cold mist and warm mist preparations.

[0055] These preparations can be produced by known methods. For example, the active compounds are mixed with extenders, which are liquid or liquefied gas or solid diluents or carriers, and surfactants, namely emulsifiers and / or dispersants and / or foam formers, can be optionally used. For example, when water is used as an extender, organic solvents can also be used as adjuvants.

[0056] When a liquid solvent is used as a diluent or carrier, it is basically suitable, 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 paraffin, 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 common polar solvents, such as dimethylformamide, dimethyl sulfoxide and water.

[0057] Liquefied gas diluents or carriers refer to liquids that will become gases at normal temperature and pressure, such as aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.

[0058] 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 granules are crushed and classified natural zircon, such as calcite, marble, pumice, sepiolite, dolomite, inorganic and organic coarse powder synthetic granules, and granules of organic materials such as sawdust, coconut shells, corn cobs and tobacco stalks, etc.

[0059] Nonionic and anionic emulsifiers can be used as emulsifying agents and / or foam formers. For example, polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, alkylaryl polyethylene glycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, and albumin hydrolysis products. Dispersants include lignin sulfite waste liquor and methyl cellulose.

[0060] Binders can be used in the formulation, 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.

[0061] Colorants can be used, such as inorganic dyes, such as iron oxide, cobalt oxide and Prussian blue; organic dyes, such as azo dyes or metal phthalocyanine dyes; trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, aluminum and zinc, etc.

[0062] These active compounds of the present invention can be present as a mixture with other active compounds in their commercial formulations or in the use forms prepared from these formulations. These other active compounds are insecticides, fungicides, fungicides, herbicides, growth control agents, etc. Insecticides include, for example, phosphate esters, carbamates, chlorinated hydrocarbons, and substances produced by microorganisms, such as avermectin, etc. Fungicides include methoxyacrylates, amides, triazoles, etc.

[0063] In addition, these active compounds of the present invention can also be present as a mixture with synergists in their commercial formulations or in the use forms prepared from these formulations. These synergists are compounds that enhance the action of the active compounds. Since the active compounds themselves are active, it is not necessary to add synergists.

[0064] These formulations usually contain 0.001-99.99% by weight, preferably 0.01-99.9% by weight, more preferably 0.05-90% by weight of the active compounds of the present invention based on the total weight of the fungicide composition. The concentration of the active compounds in the commercial formulations or use forms can vary within a wide range. The concentration of the active compounds in the use forms can range from 0.0000001-100% (g / v), preferably between 0.0001 and 1% (g / v).

[0065] The preparation method of the compound of the present invention

[0066] The compounds represented by the general formula (I) of the present invention can be prepared by the following methods. However, the conditions of the methods, such as reactants, solvents, bases, the amounts of the compounds used, reaction temperature, reaction time required, etc. are not limited to the following explanations. The compounds of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in this specification or known in the art. Such combinations can be easily carried out by those skilled in the art to which the present invention pertains.

[0067] The present invention will be further described below in conjunction with specific embodiments. It should be understood that these embodiments are only used to illustrate the present invention and not to limit the scope of the present invention. The experimental methods without specific conditions noted in the following embodiments are generally carried out under conventional conditions or according to the conditions recommended by the manufacturers. The materials can be obtained from public commercial channels unless otherwise specified. Unless otherwise stated, percentages and parts are calculated by weight.

[0068] Example 1: Preparation of 3,5-dichlorobenzyl 2-bromoacetate

[0069]

[0070] Dissolve 1 mmol of 3,5-dichlorobenzyl alcohol in 5 ml of tetrahydrofuran, then add 1 mmol of DCC and a catalytic amount of DMAP, and then add 1 mmol of bromoacetic acid. Stir at room temperature overnight and monitor the reaction by TLC. After the reaction is completed, add 5 ml of water and 5 ml of ethyl acetate, and extract the aqueous phase with ethyl acetate. Combine the organic phases, wash with saturated sodium chloride, dry over anhydrous magnesium sulfate, and evaporate the solvent. Purify the crude product by column chromatography to obtain 3,5-dichlorobenzyl 2-bromoacetate (yield 73%, colorless liquid). 1 H NMR (400 MHz, CDCl 3 d) δ: 7.33 (t, J = 1.6 Hz, 1H), 7.25 (d, J = 1.6 Hz, 2H), 5.15 (s, 2H), 4.13 (s, 2H); HRMS (ESI) m / z [M+H] + C 9 H 8 BrCl 2 O 2 , calculated value: 296.9079, measured value: 296.9069.

[0071] Example 2: Preparation of 3,5-dichlorobenzyl 2-chloroacetate

[0072]

[0073] The synthesis of the target compound is similar to that in Example 1, except that chloroacetic acid is used instead of bromoacetic acid. (Yield 66%, light yellow solid). 1 H NMR (400 MHz, CDCl 3 d) δ: 7.27 (t, J = 2.0 Hz, 1H), 7.19 (d, J = 1.9 Hz, 2H), 4.92 (s, 2H), 4.50 (s, 2H).; HRMS (ESI) m / z [M+H] + C 9 H8 Cl 3 O 2 Calculated value: 252.9584, measured value: 252.9583.

[0074] Example 3: Preparation of 3,5-dichlorobenzyl 3,3,3-trifluoropropionate

[0075]

[0076] The synthesis of the target compound was similar to that of Example 1, except that 3,3,3-trifluoropropionic acid was used instead of bromoacetic acid. (Yield 67%, colorless liquid). 1 H NMR (400 MHz, CDCl 3 d) δ: 7.34 (t, J = 1.8 Hz, 1H), 7.24 (d, J = 1.8 Hz, 2H), 5.14 (s, 2H), 3.26 (q, J = 10.0 Hz, 2H); HRMS (ESI) m / z [M+H] + C 10 H 8 Cl 2 O 2 F 3 Calculated value: 286.9848, measured value: 286.9843.

[0077] Example 4: Preparation of 3,5-dichlorobenzyl 2,2,3,3,3-pentafluoropropionate

[0078]

[0079] The synthesis of the target compound was similar to that of Example 1, except that 2,2,3,3,3-pentafluoropropionic acid was used instead of bromoacetic acid. (Yield 61%, colorless liquid). 1 H NMR (400 MHz, CDCl 3 d) δ: 7.39 (t, J = 1.8 Hz, 1H), 7.26 (d, J = 1.8 Hz, 2H), 5.31 (s, 2H); HRMS (ESI) m / z [M+H] + C 10 H 5 Cl 2 O 2 F 5 Calculated value: 321.9587, measured value: 321.9587.

[0080] Example 5: Preparation of 3,5-dichlorobenzyl 2,2,3,3,4,4,4-heptafluorobutyrate

[0081]

[0082] The synthesis of the target compound was similar to that of Example 1, except that 2,2,3,3,4,4,4-heptafluorobutyric acid was used instead of bromoacetic acid. (Yield 62%, colorless liquid). 1 H NMR(400MHz,CDCl 3 d)δ:7.35(t,J=2.6Hz,1H),7.28(d,J=1.8Hz,2H),4.44(s,2H);HRMS(ESI)m / z[M+H] + C 11 H 6 Cl 2 O 2 F 7 , calculated value: 372.9628, measured value: 372.9628.

[0083] Example 6: Preparation of 3,5-dichlorobenzyl 2,2,2-trichloroacetate

[0084]

[0085] The synthesis of the target compound was similar to that of Example 1, except that 2,2,2-trichloroacetic acid was used instead of bromoacetic acid. (Yield 65%, yellow solid). 1 H NMR(400MHz,CDCl 3 d)δ:7.37(t,J=1.8Hz,1H),7.30(d,J=1.8Hz,2H),5.30(s,2H);HRMS(ESI)m / z[M+H] + C 9 H 6 Cl 5 O 2 , calculated value: 320.8805, measured value: 320.8815.

[0086] Example 7: Preparation of 3,5-dichlorobenzyl 4-bromobutyrate

[0087]

[0088] The synthesis of the target compound was similar to that of Example 1, except that 4-bromobutyric acid was used instead of bromoacetic acid. (Yield 61%, yellow solid). 1 H NMR(400MHz,CDCl 3d) δ: 7.25 (t, J = 1.8 Hz, 1H), 7.16 (d, J = 1.8 Hz, 2H), 4.99 (s, 2H), 3.40 (t, J = 7.4 Hz, 2H), 2.52 (t, J = 7.2 Hz, 2H), 2.17 - 2.08 (m, 2H); HRMS(ESI) m / z [M + H] + C 9 H 6 Cl 5 O 2 , calculated value: 324.9392, found value: 324.9391.

[0089] Example 8: Preparation of 3,5 - Dichlorobenzyl 4 - Chlorobenzoate

[0090]

[0091] The synthesis of the target compound was similar to that of Example 1, except that 4 - chlorobenzoic acid was used instead of bromoacetic acid. (Yield 69%, white solid). 1 H NMR(400MHz, CDCl 3 d) δ: 7.97 (d, J = 8.7 Hz, 2H), 7.61 (d, J = 8.5 Hz, 2H), 7.25 (t, J = 1.8 Hz, 1H), 7.16 (d, J = 1.8 Hz, 2H), 4.99 (s, 2H); HRMS(ESI) m / z [M + H] + C 14 H 10 Cl 3 O 2 , calculated value: 314.9741, found value: 314.9740.

[0092] Example 9: Preparation of 3,5 - Dichlorobenzyl 4 - Methoxybenzoate

[0093]

[0094] The synthesis of the target compound was similar to that of Example 1, except that 4 - methoxybenzoic acid was used instead of bromoacetic acid. (Yield 68%, white solid). 1 H NMR(400MHz, CDCl 3 d) δ: 8.10 (d, J = 8.9 Hz, 2H), 7.25 (t, J = 1.8 Hz, 1H), 7.20 (d, J = 8.9 Hz, 2H), 7.16 (d, J = 1.8 Hz, 2H), 4.99 (s, 2H), 3.89 (s, 3H); HRMS(ESI) m / z [M + H] + C 15 H 13Cl 2 O 3 , Calculated value: 311.0236, Measured value: 311.0231.

[0095] Example 10: Preparation of 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid 3,5-dichlorobenzyl ester

[0096]

[0097] The synthesis of the target compound is similar to that of Example 1, except that 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid is used instead of bromoacetic acid. (Yield 62%, white solid). 1 H NMR(400MHz,CDCl 3 d)δ:8.71(s,1H),7.29(t,J=56Hz,1H),7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H),5.21(s,2H),3.82(s,3H);HRMS(ESI)m / z[M+H] + C 13 H 11 Cl 2 O 2 N 2 F 2 , Calculated value: 335.0160, Measured value: 335.0161.

[0098] Example 11: Preparation of 3,5-dichlorobenzyl 2,2,2-trifluoroacetate

[0099]

[0100] The synthesis of the target compound is similar to that of Example 1, except that trifluoroacetic acid is used instead of bromoacetic acid. (Yield 61%, colorless liquid). 1 H NMR(400MHz,CDCl 3 d)δ:7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H),5.21(s,2H);HRMS(ESI)m / z[M+H] + C 9 H 6 Cl 2 O 2 F 3 , Calculated value: 272.9691, Measured value: 272.9692.

[0101] Example 12: Preparation of N-(3,5-dichlorophenyl)-2,2,2-trifluoroacetamide

[0102]

[0103] The synthesis of the target compound was similar to that of Example 1, except that trifluoroacetic acid was used instead of bromoacetic acid, and 3,5-dichloroaniline was used instead of 3,5-dichlorobenzyl alcohol. (Yield 68%, white solid). 1 H NMR(400MHz,CDCl 3 d)δ:7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H);HRMS(ESI)m / z[M+H] + C 8 H 5 Cl 2 ONF 3 , calculated value: 257.9695, measured value: 257.9691.

[0104] Example 13: Preparation of 3,5-dichlorophenyl 2,2,2-trifluoroacetate

[0105]

[0106] The synthesis of the target compound was similar to that of Example 1, except that trifluoroacetic acid was used instead of bromoacetic acid, and 3,5-dichlorophenol was used instead of 3,5-dichlorobenzyl alcohol. (Yield 61%, white solid). 1 H NMR(400MHz,CDCl 3 d)δ:7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H);HRMS(ESI)m / z[M+H] + C 8 H 4 Cl 2 O 2 F 3 , calculated value: 258.9535, measured value: 258.9531.

[0107] Example 14: Preparation of 3,5-dichlorophenethyl 2,2,2-trifluoroacetate

[0108]

[0109] The synthesis of the target compound was similar to that of Example 1, except that trifluoroacetic acid was used instead of bromoacetic acid, and 3,5-dichlorophenethyl alcohol was used instead of 3,5-dichlorobenzyl alcohol. (Yield 63%, white solid). 1 H NMR(400MHz,CDCl 3d) δ: 7.25 (t, J = 1.8 Hz, 1H), 7.16 (d, J = 1.8 Hz, 2H), 4.12 (t, J = 6.8 Hz, 2H), 3.50 (t, J = 6.8 Hz, 2H); HRMS(ESI) m / z [M + H] + C 10 H 8 Cl 2 O 2 F 3 , calculated value: 286.9848, measured value: 286.9841.

[0110] Example 15: Preparation of 3,5-Dichlorobenzyl 4-(Trifluoromethoxy)benzoate

[0111]

[0112] The synthesis of the target compound was similar to that of Example 1, except that 4-(trifluoromethoxy)benzoic acid was used instead of bromoacetic acid (yield 63%, white solid). 1 1H NMR (400 MHz, CDCl 3 d) δ: 7.91 (d, J = 8.7 Hz, 2H), 7.25 (t, J = 1.8 Hz, 1H), 7.16 (d, J = 1.8 Hz, 2H), 7.04 (d, J = 8.5 Hz, 2H), 5.01 (s, 2H); HRMS(ESI) m / z [M + H] + C 15 H 10 Cl 2 O 3 F 3 , calculated value: 364.9954, measured value: 364.9953.

[0113] Example 16: Preparation of 3,5-Dichlorophenyl 4-(Trifluoromethoxy)benzoate

[0114]

[0115] The synthesis of the target compound was similar to that of Example 1, except that 4-(trifluoromethoxy)benzoic acid was used instead of bromoacetic acid, and 3,5-dichlorophenol was used instead of 3,5-dichlorobenzyl alcohol (yield 71%, yellow solid). 1 1H NMR (400 MHz, CDCl 3 d) δ: 7.91 (d, J = 8.7 Hz, 2H), 7.25 (t, J = 1.8 Hz, 1H), 7.16 (d, J = 1.8 Hz, 2H), 7.04 (d, J = 8.5 Hz, 2H); HRMS(ESI) m / z [M + H] + C 14H 8 Cl 2 O 3 F 3 , Calculated value: 350.9797, Measured value: 350.9781.

[0116] Example 17: Preparation of 3,5-Dimethylbenzyl 3,3,3-Trifluoropropionate

[0117]

[0118] The synthesis of the target compound was similar to that of Example 1, except that 3,3,3-trifluoropropionic acid was used instead of bromoacetic acid, and 3,5-dimethylbenzyl alcohol was used instead of 3,5-dichlorobenzyl alcohol (yield 50%, yellow solid). 1 H NMR(400MHz,CDCl 3 d)δ:7.02(s,1H),7.00(s,2H),5.28(s,2H),3.26(q,J=10.0Hz,2H),2.33(s,6H); HRMS(ESI)m / z[M+H] + C 12 H 14 O 2 F 3 , Calculated value: 247.0940, Measured value: 247.0941.

[0119] Example 18: Preparation of 3,5-Dimethoxybenzyl 3,3,3-Trifluoropropionate

[0120]

[0121] The synthesis of the target compound was similar to that of Example 1, except that 3,3,3-trifluoropropionic acid was used instead of bromoacetic acid, and 3,5-dimethoxybenzyl alcohol was used instead of 3,5-dichlorobenzyl alcohol (yield 50%, yellow solid). 1 H NMR(400MHz,CDCl 3 d)δ:6.45 - 6.41(m,3H),5.36(s,2H),3.78(s,6H),3.26(q,J=10.0Hz,2H); HRMS(ESI)m / z[M+H] + C 12 H 14 O 4 F 3 , Calculated value: 279.0839, Measured value: 279.0831.

[0122] Example 19: Preparation of 3,5-Dibromobenzyl 3,3,3-Trifluoropropionate

[0123]

[0124] The synthesis of the target compound was similar to that of Example 1, except that 3,3,3-trifluoropropionic acid was used instead of bromoacetic acid, and 3,5-dibromobenzyl alcohol was replaced by 3,5-dichlorobenzyl alcohol (yield 52%, yellow solid). 1 H NMR(400MHz,CDCl 3 d)δ:7.58(t,J = 1.7Hz,1H),7.43 - 7.39(m,2H),4.44(s,2H),3.26(q,J = 10.0Hz,2H);HRMS(ESI)m / z[M+H] + C 10 H 8 O 3 F 3 Br 2 , calculated value: 374.8838, measured value: 374.8831.

[0125] Example 20: Preparation of 2,4-dichlorobenzyl 3,3,3-trifluoropropionate

[0126]

[0127] The synthesis of the target compound was similar to that of Example 1, except that 3,3,3-trifluoropropionic acid was used instead of bromoacetic acid, and 2,4-dichlorobenzyl alcohol was replaced by 3,5-dichlorobenzyl alcohol (yield 53%, yellow liquid). 1 H NMR(400MHz,CDCl 3 d)δ:7.40(d,J = 8.3Hz,1H),7.35(d,J = 2.1Hz,1H),7.24(dd,J = 8.3,2.0Hz,1H),4.71(s,2H),3.26(q,J = 10.0Hz,2H);HRMS(ESI)m / z[M+H] + C 10 H 8 O 2 F 3 Cl 2 , calculated value: 286.9848, measured value: 286.9842.

[0128] Other compounds in Table 1 were synthesized by a method similar to that of Examples 1 - 20.

[0129] Example 21: Antibacterial Activity Test of the Compounds of the Invention

[0130] The host crops were cucumber (cultivar Xintaimici), wheat (cultivar Liaochun 10), and corn (Jinhuanuo 2) respectively.

[0131] Weigh 0.0088 g of the new compound and dissolve it in 2 ml of acetone. Add water containing 0.1% Tween 80 to prepare 20 ml of a 400 mg / L liquid medicine. Prepare another control medicine, 20 ml of azoxystrobin liquid medicine, for in-vivo screening.

[0132] Cucumber seedlings at the two-leaf stage grown in the greenhouse are used as the test host plants for cucumber downy mildew, wheat seedlings at the two-leaf stage are used as the test host plants for wheat powdery mildew, and corn seedlings at the two-leaf stage are used as the test host plants for corn rust.

[0133] The type of sprayer is a three-dimensional crop sprayer, and the spray pressure is 1.5 kg / cm 2 , and the liquid spraying amount is about 1000 L / hm 2 , treat the above test materials, then air-dry them naturally, and inoculate the pathogenic bacteria after 24 h.

[0134] Use an inoculator to spray the sporangium suspension of cucumber downy mildew pathogen (5×10 5 spores / ml) and the spore suspension of corn rust pathogen (5×10 6 spores / ml) onto the host crops, and transfer them to an artificial climate chamber for cultivation (24 °C, RH>90, no light). After culturing the test materials for cucumber downy mildew and corn rust for 24 h, transfer them to the greenhouse for normal management, and investigate the bactericidal activity of the compound after 4 d.

[0135] Shake the spores of the powdery mildew pathogen onto the wheat leaves and culture them in the greenhouse. Investigate the bactericidal activity of the compound after 7 d.

[0136] The result investigation refers to "A Manual of Assessment Keys for Plant Diseases" compiled by the American Phytopathological Society, which is represented by 100 - 0, with "100" representing no disease and "0" representing the most severe disease degree.

[0137]

[0138]

[0139] Example 22: Antibacterial activity test of the compound of the present invention

[0140] Take the new compound and dissolve it in 1 ml of dimethyl sulfoxide to prepare a 2000 mg / L liquid medicine. Prepare another 1 ml of liquid medicine of the control agents boscalid and boscalid at 25 mg / L for in-vitro screening.

[0141] In the pre-cultured Petri dishes of rice sheath blight and cucumber gray mold pathogens, add deionized water, gently scrape the spores on the surface of the mycelium, filter with 3 - 5 layers of gauze, then put them into a centrifuge tube, centrifuge at low speed (1000 rpm) for 5 minutes, pour off the supernatant, add deionized water again, and centrifuge again. Dilute the precipitated spores with an appropriate amount of deionized water to a spore suspension with about 100 spores under a 100-fold microscope.

[0142] Add the prepared liquid medicine to a 96-well culture plate, with 4 replicates for each medicine, 1 μL per well. Then add the prepared spore suspension, 79 μL per well. Incubate the rice sheath blight at 28 °C in a dark incubator for 18 h, and incubate the cucumber gray mold at 18 °C in a dark incubator for 18 h, then conduct the investigation.

[0143]

[0144]

[0145] The antibacterial results of each compound are shown in Table 1.

[0146] Table 1 Antibacterial Activity of Compounds of Formula (I)

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166] Example 23: Composition Containing the Fungicide of the Compound of the Present Invention

[0167] (a) Microemulsion

[0168] Prepare the following components in proportion: 5.0% (weight percentage, the same below) of any one of Compounds I-1 to I-201 (Table 1); 30.0% of polyvinylpyrrolidone-vinyl acetate copolymer; 30.0% of alkyl polyglycoside; 15.0% of glyceryl oleate; 20.0% of water.

[0169] (b) Wettable Powder

[0170] Prepare the following components in proportion: 65.0% of any one of Compounds I-1 to I-201 (Table 1); 2.0% of dodecylphenol polyethylene glycol ether; 4.0% of sodium lignosulfonate; 6.0% of sodium aluminosilicate; 23.0% of montmorillonite (calcined).

[0171] (c) Seed Treatment Agent

[0172] Prepare the following components in proportion: 20.00% of any one of Compounds I-1 to I-201 (Table 1); 5.00% of polyvinylpyrrolidone-vinyl acetate copolymer; 5.00% of montanic acid wax; 1.00% of calcium lignosulfonate; 1.00% of polyoxyethylene / polyoxypropylene block copolymer; 2.00% of stearyl alcohol (POE 20); 0.20% of polyorganosilicon; 0.05% of coloring agent red dye; 65.75% of water.

[0173] After reading the above teachings of the present invention, those skilled in the art can make various changes or modifications to the present invention, and these equivalent forms also fall within the scope defined by the appended claims of this application.

Claims

1. Use of a compound having the structure shown in general formula (I) or a pesticidally acceptable salt thereof, characterized in that, it is used for controlling plant pathogens, wherein, the control of plant pathogens refers to controlling a variety of the following diseases: cucumber downy mildew, cucumber gray mold, rice sheath blight; the compound is any one of the following compounds, 2. A compound having the structure shown in general formula (I) or a pesticidally acceptable salt thereof, wherein, the compound is any one of the following compounds, 3. A pesticidal composition, characterized in that, it comprises: (a) the compound described in claim 2 or a pesticidally acceptable salt thereof, or a combination thereof; and (b) a pesticidally acceptable carrier and / or excipient.

4. The pesticidal composition according to claim 3, characterized in that, The pesticide composition also includes: flumorph, chloranil, sulfaquinoxaline, mesocyanate, thiophanate-methyl, cyfluanid, cyfluanid, streptothiopyrad, penthiopyrad, cyclamoxadone, oxazolidinone, cyproconazole, cyproconazole, cyanamide, dichlorocyanamide, carboxin, furapyramide, furamide, flutolanil, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fluoxastrobin, enoxastrobin, fenoxystrobin, enoxastrobin, trifloxystrobin, trifloxystrobin, imazalil, imazalil, imazalil, imazalil, oxazolidinone, cyproconazole, imazalil, prochloraz, oxaquinoxaline ... azole, fenpropimorph, tetrafluconazole, tebuconazole, flusilane, silfluazole, triazole, cyproconazole, diniconazole, flutriafol, hexaconazole, prothioconazole, trithionazole, penconazole, myclobutanil, myclobutanil, imipenazole, saccharoconazole, cyproconazole, metconazole; thiabendazole, benzathiathionine, octhiocarb, carbendazim, dodecacyclic morpholine, fenpropimorph, tridecanone; flutolanil, fludioxonil, fluazinam, boscalid, flubosaccharide, pyraclostrobin, pyrimidine, chlorfenapyr, flufenapyr, pyrimidine, pyrimidine, myclobutanil, myclobutanil, fluazinam, mite-killing agent, dimethoate, Cyanoanthraquinone, ethoxyquinoline, 8-hydroxyquinoline, propoxyquinoline, phenoxyquinoline, isoprofenamide, ethotripsy, benzthiopyrad, propamocarb, thiocarb, dichlorvos, isoprofen, pyraclostrobin, methyl tolclorox, oxazolidinone, blasticidin, kasugamycin, polyoxin, polyoxin, activated ester, indole ester, bronopol, benzylsulfuron, toluenesulfuron, spiroxafil, thiamethoxam, sodium disulfuron, pencuron, tetrachlorophthalide, tricyclazole, allylbenzyl, fenpropidin, chloranil, biguanide, dococin, streptomycin, metalaxyl, propantheline, bensulfuron, leaf dregs, Jinggangmycin, pentachloronitrate Benzene, mancozeb, fosetyl-aluminum, ethoxysulfonate, ethoxyphenol, dimethoate, triadimefon, methyl thiophanate, carbendazim, benomyl, captan, difopicolide, sulfamethoxam, furamide, sclerotin, thiram, rice blast, rice blast, chlorothalonil, sulfur, Bordeaux mixture, cuprous oxide, cupric sulfate, matrine, osthole, knotweed extract, camphor, copper humate, copper rosinate, sodium rosinate, mixed amino acid copper, copper succinate, copper citrate, eugenol, carvacrol, berberine, allicin, chitosan, oligosaccharides, glucan or allicin.

5. A method for preventing and controlling plant pathogens, It is characterized in that The method comprises applying the compound according to claim 2 or its pesticide acceptable salt or the pesticide composition according to claim 3 to plants, wherein the plant pathogens are multiple species of cucumber downy mildew, cucumber gray mold, and rice sheath blight.

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