Sydney ketone and Sydney ketimine compounds and preparation methods and uses thereof

Abstract

The present invention discloses Sydney ketone and Sydney ketimine compounds and preparation methods and uses thereof. The compound structures are 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 fungicidal activity against various plant fungal diseases, and can be used alone or in combination with other agents for the prevention and treatment of various plant fungal diseases, especially having excellent prevention and treatment effects on cucumber downy mildew, cucumber anthracnose, wheat powdery mildew, corn rust, rice sheath blight, and cucumber gray mold.

Description

Technical Field

[0001] The invention relates to Sydney ketone and Sydney ketimine compounds and preparation methods and uses thereof. Background Art

[0002] Plant pathogens are very harmful to plant growth and cause huge losses to agriculture every year. In order to prevent the occurrence of plant diseases and reduce the losses caused by them, a large number of antibacterial and fungicidal 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 for pesticide companies and researchers.

[0003] Sydney ketone or Sydney ketone imine compounds are the most widely studied mesoionic compounds. Compounds of this structure have a wide range of biological activities, including anticancer, antiviral, analgesic, antispasmodic, antipyretic, free radical scavenging and nitric oxide donor activities. Further development is needed. Summary of the invention

[0004] The purpose of the present invention is to provide a novel compound containing Sydney ketone or Sydney ketimine structure for preventing and controlling plant pathogens.

[0005] In a first aspect of the present invention, there is provided a compound having a structure represented by general formula (I), an optical isomer, a cis-trans isomer or a pesticide-acceptable salt thereof,

[0006]

[0007] In the formula, L is H, halogen (such as fluorine, chlorine, bromine, iodine), hydroxyl, nitro, carboxyl, cyano, SHSF5, SCN, or a substituted or unsubstituted group selected from the following group: C1-C8 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C2-C6 alkenyloxy, C2-C6 alkynyl, C2-C6 alkynyloxy, C1-C6 alkoxy, C3-C6 cycloalkyloxy, C5-C7 cycloalkenyl, 4-8 membered heterocyclyl, -CONR a R b 、C6-C 10 Aryl, -C(O)(C6-C 10 Aryl), -COO(C6-C 10 Aryl), -COO(C6-C 10 Aryl)(C2-C6 alkenyl), -COO(C1-C8 alkylene)(C6-C 10 aryl), -COO(C1-C8 alkylene)phenyl(C2-C6 alkenyl), 4-8 membered heteroaryl, -(C1-C8 alkylene)(4-10 membered heteroaryl), -(C1-C8 alkylene)(C6-C 10 Aryl), -C(O)(C1-C8 alkylene)(C6-C 10aryl), -(C1-C8 alkylene)(C3-C6 cycloalkyl), -C(O)(C1-C8 alkyl), -C(O)(4-8 membered heteroaryl), -C(O)(4-8 membered heterocyclyl), -C(O)(C3-C6 cycloalkyl), -(C1-C8 alkylene)(4-10 membered heterocyclyl), -(C1-C8 alkylene)NHCO(4-10 membered heteroaryl), -NR a R b ; where R a , R b Each independently selected from H, C1-C8 alkyl, C3-C6 cycloalkyl, C1-C8 haloalkyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group; wherein the substitution refers to substitution by one or more groups selected from the following group: cyano, hydroxyl, oxo (=O), C1-C8 alkyl, halogen (fluorine, chlorine, bromine), C1-C8 haloalkyl, -CONH (C1-C8 alkyl), C3-C6 cycloalkyl, C1-C8 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, nitro, C2-C6 alkynyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclyl, -COO(C1-C8 alkyl) or C1-C6 thioalkyl;

[0008] Q is a substituted or unsubstituted group selected from the following group: C1-C 10 Alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 10 aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group, -(C1-C8 alkylene)(C3-C6 cycloalkyl), -(C1-C8 alkylene)(C6-C 10 aryl), -(C1-C8 alkylene)(4-10 membered heteroaryl), -(C1-C8 alkylene)(4-8 membered heterocyclyl), -C(O)(C6-C 10 aryl), -C(O)(4-8 membered heteroaryl), -C(O)(C1-C 10 alkyl), -C(O)(C3-C6 cycloalkyl), -C(O)(4-8 membered heterocyclic), -COO(C6-C 10 Aryl), -COO (4-8 membered heteroaryl), -COO (C1-C 10 alkyl), -COO(C3-C6 cycloalkyl), -COO(4-8 membered heterocyclic group), -C(O)(C6-C 10 Aryl)NHCO (4-10 membered heteroaryl), -(C6-C 10 Aryl)(C6-C 10 Aryl)NHCO (4-10 membered heteroaryl), -(C6-C 10Aryl)NHCO (4-10 membered heteroaryl), -CONR c R d 、-NR c R d ; where R c , R d Each independently selected from: hydrogen, C1-C8 alkyl, C3-C6 cycloalkyl, C1-C8 haloalkyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group, -C(O)(C6-C 10 wherein the substitution refers to substitution by one or more groups selected from the group consisting of cyano, oxo (=O), C1-C8 alkyl, halogen (fluorine, chlorine, bromine), C1-C8 haloalkyl, halogenated 4-8 membered heteroaryl, -CONH (C1-C8 alkyl), C3-C6 cycloalkyl, C1-C8 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, nitro, hydroxyl, C2-C6 alkynyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group, -O(C6-C 10 Aryl) or C1-C6 thioalkyl;

[0009] M is O - or N - R 1 ; Among them, R 1 is a substituted or unsubstituted group selected from the following group: -COO(C1-C8 alkyl), -SO2(C1-C8 alkyl), -C(O)(C1-C8 alkyl), -C(O)(C6-C 10 Aryl), -SO2(C6-C 10 aryl), -C(O)(4-8 membered heteroaryl), -P(O)(OC1-C8 alkyl)(OC1-C8 alkyl), -CO(C1-C8 alkylene)(4-8 membered heterocyclic group), -COO(C6-C 10 aryl), -COO(4-8 membered heteroaryl), -COO(C3-C8 cycloalkyl), -COO(4-8 membered heterocyclyl), -SO2(C3-C8 cycloalkyl), -SO2(4-8 membered heteroaryl), -SO2(4-8 membered heterocyclyl), -C(O)(C3-C8 cycloalkyl), -C(O)(4-8 membered heterocyclyl), -CO(C1-C8 alkylene)(C3-C8 cycloalkyl), -CO(C1-C8 alkylene)(C6-C 10 aryl), -CO(C1-C8 alkylene)(4-8 membered heteroaryl), -CO(C1-C8 alkylene)(C3-C8 cycloalkyl), -SO(C1-C8 alkyl), -SO(C6-C 10aryl), -SO(C3-C8 cycloalkyl), -SO(4-8 membered heteroaryl), -SO(4-8 membered heterocyclyl), -CONR e R f , where R e , R f independently selected from H, C1-C8 alkyl, C3-C6 cycloalkyl, C1-C8 haloalkyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclic group; wherein the substitution refers to substitution by one or more groups selected from the following groups: halogen (fluorine, chlorine, bromine), cyano, C1-C8 alkyl, C1-C8 haloalkyl, nitro, hydroxyl, C2-C6 alkenyl, C2-C6 alkynyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 thioalkyl.

[0010] In another preferred embodiment, M is O - or N - R 1 ; Among them, R 1 is a substituted or unsubstituted group selected from the following group: -COO(C1-C6 alkyl), -SO2(C1-C4 alkyl), -C(O)(C1-C4 alkyl), -C(O)phenyl, -SO2phenyl, -C(O)(5-6 membered heteroaryl), -P(O)(OC1-C4 alkyl)(OC1-C4 alkyl), -CO(C1-C4 alkylene)(5-6 membered heterocyclyl), -COOphenyl, -COO(5-6 membered heteroaryl), -COO(C3-C6 cycloalkyl), -COO(5-6 membered heterocyclyl), -SO2(C3-C6 cycloalkyl), -SO 2(5-6 membered heteroaryl), -SO2(5-6 membered heterocyclyl), -C(O)(C3-C6 cycloalkyl), -C(O)(5-6 membered heterocyclyl), -CO(C1-C4 alkylene)(C3-C6 cycloalkyl), -CO(C1-C4 alkylene)phenyl, -CO(C1-C4 alkylene)(5-6 membered heteroaryl), -CO(C1-C4 alkylene)(C3-C6 cycloalkyl), -SO(C1-C4 alkyl), -SOphenyl, -SO(C3-C6 cycloalkyl), -SO(5-6 membered heteroaryl), -SO(5-6 membered heterocyclyl), -CONR e R f , where R e , R fIndependently selected from H, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, phenyl, 4-8 membered heteroaryl, 5-6 membered heterocyclyl; wherein the substitution refers to substitution by one or more groups selected from the following groups: halogen (fluorine, chlorine, bromine), cyano, C1-C4 alkyl, C1-C4 haloalkyl, nitro, hydroxyl, C2-C4 alkenyl, C2-C4 alkynyl, phenyl, 5-6 membered heteroaryl, 5-6 membered heterocyclyl, C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 thioalkyl.

[0011] In another preferred embodiment, R 1 is a substituted or unsubstituted group selected from the following group: -COO(C1-C6 alkyl), -SO2(C1-C4 alkyl), -C(O)(C1-C4 alkyl), -C(O)phenyl, -SO2phenyl, -C(O)(5-6 membered heteroaryl), -P(O)(OC1-C4 alkyl)(OC1-C4 alkyl), -CO(C1-C4 alkylene)(5-6 membered heterocyclyl); wherein the substitution refers to substitution by one or more groups selected from the following group: halogen (fluorine, chlorine, bromine), cyano, C1-C4 alkyl, C1-C4 haloalkyl.

[0012] In another preferred embodiment, R 1 It is -COO(C1-C6 alkyl), -SO2(C1-C4 alkyl) substituted or unsubstituted by halogen(fluorine), -C(O)phenyl substituted or unsubstituted by halogen and / or cyano, -SO2phenyl substituted or unsubstituted by C1-C4 alkyl, -C(O)(C1-C4 alkyl) substituted or unsubstituted by halogen(fluorine, chlorine), -C(O)(5-6 membered heteroaryl) substituted or unsubstituted by C1-C4 alkyl and C1-C4 haloalkyl, -CO(C1-C4 alkylene) (5-6 membered heterocyclyl), -P(O)(OC1-C4 alkyl)(OC1-C4 alkyl), -C(O)(5-6 membered heteroaryl) substituted by halogen(chlorine) and / or C1-C4 haloalkyl, or -C(O)phenyl substituted by haloalkyl.

[0013] In another preferred embodiment, R 1 The groups listed in Table 1.

[0014] In another preferred embodiment, R 1 for

[0015]

[0016] In another preferred embodiment, L is H, fluorine, chlorine, bromine, iodine, hydroxyl, nitro, carboxyl, cyano, SHSF5, SCN, or a substituted or unsubstituted group selected from the following group: C1-C4 alkyl, C2-C4 alkenyl, C3-C6 cycloalkyl, C2-C4 alkenyloxy, C2-C4 alkynyl, C2-C4 alkynyloxy, C1-C4 alkoxy, C3-C6 cycloalkyloxy, C5-C6 cycloalkenyl, 5-6 membered heterocyclyl, -CONR a R b , phenyl, -C(O)phenyl, -COOphenyl, -COOphenyl(C2-C4alkenyl), -COO(C1-C4alkylene)phenyl(C2-C4alkenyl), -COO(C1-C4alkylene)phenyl, 5-6 membered heteroaryl, -(C1-C4alkylene)(4-10 membered heteroaryl), -(C1-C4alkylene)phenyl, -C(O)(C1-C4alkylene)phenyl, -(C1-C4alkylene)(C3-C6cycloalkyl), -C(O)(C1-C4alkyl), -C(O)(5-6 membered heteroaryl), -C(O)(5-6 membered heterocyclyl), -C(O)(C3-C6cycloalkyl), -(C1-C4alkylene)(5-10 membered heterocyclyl), -(C1-C4alkylene)NHCO(4-10 membered heteroaryl), -NR a R b ; where R a , R b Each is independently selected from H, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, phenyl, 5-6 membered heteroaryl, 5-6 membered heterocyclyl; wherein the substitution refers to substitution by one or more groups selected from the following group: cyano, hydroxyl, oxo (=O), C1-C4 alkyl, halogen (fluorine, chlorine, bromine), C1-C4 haloalkyl, -CONH(C1-C4 alkyl), C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyl, nitro, C2-C4 alkynyl, phenyl, 5-6 membered heteroaryl, 5-6 membered heterocyclyl, -COO(C1-C4 alkyl) or C1-C4 thioalkyl.

[0017] In another preferred embodiment, L is H, fluorine, chlorine, bromine, iodine or a substituted or unsubstituted group selected from the following group: C1-C4 alkyl, -CONR a R b , phenyl, -C(O)phenyl, -COOphenyl, -COOphenyl(C2-C4alkenyl), -COO(C1-C4alkylene)phenyl(C2-C4alkenyl), -COO(C1-C4alkylene)phenyl, 5-6 membered heteroaryl, -(C1-C4alkylene)(4-10 membered heteroaryl), -(C1-C4alkylene)(5-10 membered heterocyclyl), -(C1-C4alkylene)NHCO(4-10 membered heteroaryl); wherein Ra , R b Each is independently selected from H, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, phenyl; wherein the substitution refers to substitution by one or more groups selected from the following group: cyano, hydroxyl, oxo (=O), C1-C4 alkyl, halogen (fluorine, chlorine, bromine), C1-C4 haloalkyl, -CONH(C1-C4 alkyl), C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, or -COO(C1-C4 alkyl).

[0018] In another preferred embodiment, L is a group listed in Table 1.

[0019] In another preferred embodiment, L is H, phenyl, C1-C4 alkyl (such as ), CF3, CHF2, CH2F, Cl, Br, I or F.

[0020] In another preferred embodiment, Q is a substituted or unsubstituted group selected from the following group: C2-C 10 Alkyl, C2-C5 alkenyl, C2-C4 alkynyl, phenyl, 5-6 membered heteroaryl, 5-6 membered heterocyclyl, -(C1-C4 alkylene)(C3-C6 cycloalkyl), -(C1-C4 alkylene)(phenyl), -(C1-C4 alkylene)(5-6 membered heteroaryl), -(C1-C4 alkylene)(5-6 membered heterocyclyl), -C(O)(phenyl), -C(O)(5-6 membered heteroaryl), -C(O)(C1-C4 alkyl), -C(O )(C3-C6 cycloalkyl), -C(O)(5-6 membered heterocyclyl), -COO(phenyl), -COO(5-6 membered heteroaryl), -COO(C1-C4 alkyl), -COO(C3-C6 cycloalkyl), -COO(5-6 membered heterocyclyl), -C(O)(phenyl)NHCO(4-6 membered heteroaryl), -(phenyl)(phenyl)NHCO(4-6 membered heteroaryl), -(phenyl)NHCO(4-6 membered heteroaryl), -CONR c R d 、-NR c R d ; where R c , R dEach is independently selected from: hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, phenyl, 4-8 membered heteroaryl, 4-8 membered heterocyclyl, -C(O)(phenyl), -C(O)(4-6 membered heteroaryl); wherein the substitution refers to substitution by one or more groups selected from the following group: cyano, oxo (=O), C1-C4 alkyl, fluorine, chlorine, bromine, C1-C4 haloalkyl, halogenated 4-6 membered heteroaryl, -CONH(C1-C4 alkyl), C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyl, nitro, hydroxyl, C2-C4 alkynyl, phenyl, 5-6 membered heteroaryl, 5-6 membered heterocyclyl, -O(phenyl) or C1-C4 thioalkyl.

[0021] In another preferred embodiment, Q is a substituted or unsubstituted group selected from the group consisting of -(C1-C4 alkylene)(C3-C6 cycloalkyl), -(C1-C4 alkylene)(phenyl), -(C1-C4 alkylene)(5-6 membered heteroaryl), -(C1-C4 alkylene)(5-6 membered heterocyclyl), -C(O)(phenyl), -C(O)(5-6 membered heteroaryl), -C(O)(C1-C4 alkyl), -C(O)(C3-C6 cycloalkyl), -C(O)(5-6 membered heterocyclyl), -COO(phenyl), -COO(5-6 membered heteroaryl), -COO(C1-C4 alkyl), -COO(C3-C6 cycloalkyl), -COO(5-6 membered heterocyclyl), -C(O)(phenyl)NHCO(4-6 membered heteroaryl), -(phenyl)(phenyl)NHCO(4-6 membered heteroaryl), -(phenyl)NHCO(4-6 membered heteroaryl), -CONR c R d 、-NR c R d ; where R c , R d Each is independently selected from: hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, phenyl, 4-8 membered heteroaryl, 4-8 membered heterocyclyl, -C(O)(phenyl), -C(O)(4-6 membered heteroaryl); wherein the substitution refers to substitution by one or more groups selected from the following group: cyano, oxo (=O), C1-C4 alkyl, fluorine, chlorine, bromine, C1-C4 haloalkyl, halogenated 4-6 membered heteroaryl, -CONH(C1-C4 alkyl), C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyl, nitro, hydroxyl, C2-C4 alkynyl, phenyl, 5-6 membered heteroaryl, 5-6 membered heterocyclyl, -O(phenyl) or C1-C4 thioalkyl.

[0022] In another preferred embodiment, Q is a group listed in Table 1.

[0023] In another preferred embodiment, Q is

[0024]

[0025] In another preferred embodiment, Q is -(C1-C8 alkylene)A, and A is

[0026]

[0027] In another preferred embodiment, R 1 It is a methylcarbonyl group substituted by one or more substituents selected from hydrogen, halogen, cyano, nitro, hydroxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy or C1-C6 alkylthio substituents; preferably a trifluoromethylcarbonyl group.

[0028] In another preferred embodiment, L is hydrogen, halogen, C1-C8 alkyl, five-membered or six-membered aryl, five-membered or six-membered heteroaryl, five-membered or six-membered heteroarylaminocarbonyl, five-membered or six-membered heterocycle, five-membered or six-membered heterocyclylaminocarbonyl; the above groups are optionally mono- or poly-substituted by groups selected from the following group: hydrogen, halogen, cyano, nitro, hydroxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy or C1-C6 alkylthio.

[0029] In another preferred embodiment, L is benzyl or phenyl substituted by one or more substituents selected from hydrogen, halogen, cyano, nitro, hydroxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy or C1-C6 thioalkyl; preferably, it is phenyl substituted by trifluoromethoxy.

[0030] In another preferred embodiment, Q is C1-C8 alkyl, C1-C6 haloalkyl, five-membered or six-membered aryl, five-membered or six-membered aryl-C1-C6 alkyl, five-membered or six-membered heteroaryl, five-membered or six-membered heteroaryl-C1-C6 alkyl, five-membered or six-membered heterocycle, five-membered or six-membered heterocyclyl-C1-C6 alkyl; the above groups are optionally substituted by one or more groups selected from the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy or C1-C6 alkylthio.

[0031] In another preferred embodiment, Q is benzyl or phenyl substituted by one or more substituents selected from hydrogen, halogen, cyano, nitro, hydroxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy or C1-C6 thioalkyl; preferably 3,5-trichloro-substituted phenyl.

[0032] In another preferred embodiment, the compound is any one of the compounds in Table 1.

[0033] In another preferred embodiment, when M is O- and L is H, A or Q is not the following groups: unsubstituted phenyl or benzyl, C1-C4 alkyl-substituted phenyl or benzyl, nitro-substituted phenyl or benzyl.

[0034] In another preferred embodiment, M is O - , when A is phenyl, L is not the following groups: 3-trifluoromethylphenyl, pyridyl, C1-C2 alkoxy substituted phenyl, nitro substituted phenyl, trifluoromethyl, oxetanyl, 4-methylphenyl, iodine, amidomethylene, carboxymethylene, hydrazidemethylene, heterocyclic acyl, thiazolyl, lithium, chlorine, methylsulfonyl, morpholinomethylene acyl, pyridylmethylene acyl, chloromethylene acyl, acetyl, acyl and hydroxy substituted methylene, methylsulfinyl, thioether, methoxyformyl, phenyl, isobutyl substituted phenyl, substituted amino substituted phenyl, amide, carboxyl, N'N-diethylmethyl, N'N-dimethylmethyl.

[0035] In another preferred embodiment, M is O - , when L is acetyl, A is not the following groups: substituted phenyl, benzyl. In another preferred embodiment, M is O - , when L is amidomethylene, A is not the following group: substituted phenyl. In another preferred embodiment, M is O - , when L is methoxyacetyl, A is not the following group: substituted phenyl. In another preferred embodiment, M is O - , when A is 4-methylphenyl, L is not the following groups: formyl, bromine. In another preferred embodiment, M is O - , when A is methoxy substituted phenyl, L is not the following groups: bromoethyl, bromine, morpholinylmethylene, phenyl, N'N-diethylmethyl, N'N-dimethylethyl. In another preferred embodiment, M is O - , when L is methylenemorpholinyl, A is not the following groups: C1-C6 alkyl, benzyl. In another preferred embodiment, M is O -, when L is phenyl, A is not the following groups: N'N-dimethylmethyl, morpholine methylene, piperidine methylene, tetrahydropyrroline methylene, amide, trimethylsilyl, phenyl and hydroxy substituted methyl, allyl, nitro substituted phenyl, 4-chlorophenyl, carboxyl, thioether methylene, formic acid methylene, N'N-diethylmethyl, in another preferred embodiment, M is O - , when L is nitro, A is not the following group: nitro-substituted phenyl. In another preferred embodiment, M is O - , when L is nitro-substituted phenyl, A is not the following group: nitro-substituted phenyl. In another preferred embodiment, M is O - , when Q is propyl, A is not the following group: amide. In another preferred embodiment, M is O - , when Q is isopropyl, A is not the following group: amide group. In another preferred embodiment, M is O - , when L is phenyl and methyl substituted by hydroxyl, A is not the following groups: methylene substituted by amino. In another preferred embodiment, M is O - , when A is cyanomethylene, L is not the following groups: bromine, iodine. In another preferred embodiment, M is O - , when L is phenylacetyl, A is not the following group: amino-substituted methylene. In another preferred embodiment, M is O - , when A is phenylmethylene, L is not the following group: morpholinemethylene. In another preferred embodiment, M is O - , when A is N'N-dimethylethyl, L is not the following groups: phenylmethylene, 4-methoxyphenyl. In another preferred embodiment, M is O - , when A is N'N-dimethylmethyl, L is not the following group: 4-methoxyphenyl. In another preferred embodiment, M is O - , when L is methyl, A is not the following groups: N'N-diethylmethyl, N'N-dimethylethyl, piperidinylmethylene, tetrahydropyrromethylmethylene, mercaptomethylmethylene, phenylmethylene, N'N-dimethylmethylmethyleneoxymethyl, bromodinitromethyl, chlorodinitromethyl, thioethermethylene, phenylsubstitutedethylene, aminosulfonylmethylene, sulfonylmethylene, sulfinylmethylene, trinitromethyl, carboxyl, morpholinylmethylene. In another preferred embodiment, M is O - , when L is tert-butyl, A is not the following groups: phenyl substituted ethylene, thioether methylene. In another preferred embodiment, M is O - , when L is bromine, A is not the following groups: amide, substituted phenylacetyl, pentadecyl, ethoxyformyl, carboxyl. In another preferred embodiment, M is O - , when L is chlorine, A is not the following groups: carboxyl, amide. In another preferred embodiment, M is O -, when L is phenylmethylene, A is not the following groups: phenylmethylene, cyano, ethoxyacetyl, carboxyl, amide, N'N-dimethylethyl. In another preferred embodiment, M is O - , when A is propyl, L is not the following group: ester group. In another preferred embodiment, M is O - , when L is carboxyethylene, A is not the following group: cyanomethylene. In another preferred embodiment, M is O - , when A is an amide group, L is not the following groups: hydroxyl and phenyl substituted methyl, benzoyl, methoxyethylidene acyl. In another preferred embodiment, M is O - , when A is methoxyformyl, L is not the following groups: substituted acyl, substituted hydroxyl. In another preferred embodiment, M is O - , when A is a carboxyl group, L is not the following group: phenyl substituted with nitro. In another preferred embodiment, M is O - , when A is cyanomethylene, L is not the following groups: benzyl, isobutyl, methyl, phenyl. In another preferred embodiment, M is O - , A and L are not the following groups: C1-C4 alkyl.

[0036] In another preferred embodiment, M is BocN - , A is not the following groups: C1-C4 alkyl, methoxymethylene. In another preferred embodiment, M is benzoyl N - , A is not the following groups: methoxymethylene, C1-C4 alkyl, phenyl, amide. In another preferred embodiment, M is acetyl N - , A is not the following groups: C1-C4 alkyl, phenyl. In another preferred embodiment, M is trifluoroacetyl N - , A is not the following group: C1-C4 alkyl. In another preferred embodiment, M is butylamino acyl N - , A is not the following group: C1-C4 alkyl. In another preferred embodiment, M is methylamino acyl N - , A is not the following groups: ester group, amide group, phenyl group. In another preferred embodiment, M is methoxy acyl group N - , A is not the following group: C1-C4 alkyl. In another preferred embodiment, M is an aniline acyl group N - , A is not the following groups: amide group, ester group, carboxyl group.

[0037] The second aspect of the present invention provides a pesticide composition comprising:

[0038] (a) the compound of the first aspect, its optical isomers, cis-trans isomers or pesticide-acceptable salts thereof, or a combination thereof; and

[0039] (b) pesticide-acceptable carriers and / or excipients.

[0040] In another preferred embodiment, 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 %.

[0041] When necessary, one or more acceptable carriers in pesticide preparations may be added to the pesticide composition, including conventional diluents, excipients, fillers, adhesives, wetting agents, absorption promoters, surfactants, lubricants, stabilizers, defoamers, diatomaceous earth, etc. The dosage form of the prepared drug is also diverse, which may be powder, emulsion, aqueous solution, granules, corrosion inhibitors, effervescent tablets, etc.

[0042] In another preferred embodiment, the pesticide composition further comprises: flumorph, fenacetyl morpholine, chloranil, sulfamethoxam, sulfamethoxam, thiofluanid, cyfluanid, streptothiopyrad, penthiopyrad, cyclamoxadone, oxazolidinone, cyproconazole, thiocarbamide, cyanamide, dichlorocyanamide, high-efficiency metalaxyl, high-efficiency bensulfuron, carboxin, furapyramide, furamide, flutolanil, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fluoxastrobin, enoxamethoxam, fenoxystrobin, trifloxystrobin, enoxamethoxam, trifloxystrobin ... , fluquinconazole, fluquinconazole, fenpropimorph, tetrafluconazole, tebuconazole, flusilane, siloxane, triazole, bifenthrin, cyproconazole, high-efficiency diniconazole, diniconazole, flutriafol, hexaconazole, prothioconazole, trithionazole, penconazole, myclobutanil, nitrobenzazole, imidoazole, sugar conidiaazole, cyproconazole, metconazole; thiazoles: triathiapiprolin, benzathiathionine, octhiazide, carbendazim, dodecacyclic morpholine, fenpropimorph, tridecanone; pyrroles: fenpiclonil, fludioxonil, fluazinam, boscalid, flubosaccharid, pyraclostrobin, cyclamoxadone, pyraclostrobin, pyrimidine cyclamine, chlorfenapyr, flufenapyr, pyrimidine amide, myclobutanil, myclobutanil, myclobutanil, fluazinam, acaricide Manganese, dicyanoanthraquinone, 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, benzsulfamide, tolusulfamide, spiroxafil, thiamethoxam, sodium disulfone, pencuron, tetrachlorophthalide, tricyclazole, allylbenzamide, fenpropidin, chloranil, biguanide, docodine, frost, succinate, benzophenone, succinate, streptomycin, metalaxyl, propantheline, bensulfamide, leaf dregs, validamycin, Jinggangmycin , pentachloronitrobenzene, mancozeb, fosetyl-aluminum, ethoxysulfonate, ethoxyphenol, dimethoate, triadimefon, methyl thiophanate, carbendazim, benomyl, captan, captan, sulfamethoxam, fumarate, furamide, fluchlorinated sclerotin, vinyl sclerotin, sclerotin, thiram, rice blast, rice blast, chlorothalonil, sulfur, Bordeaux mixture, hydroxide mace, cuprous oxide, copper oxide, copper sulfate, matrine, osthole, knotweed extract, camphor, copper humate, copper rosinate (sodium), mixed amino acid copper, copper succinate, copper citrate, eugenol, carvacrol, berberine, allicin, chitosan, oligosaccharides, glucan, allicin.

[0043] The third aspect of the present invention provides the use of the compound described in the first aspect, its optical isomers, cis-trans isomers or pesticide-acceptable salts, or the pesticide composition described in the second aspect for controlling plant diseases or preparing fungicides.

[0044] In another preferred embodiment, the plant disease is a plant fungal disease.

[0045] In another preferred embodiment, the fungicide prevents and controls the following diseases: anthracnose, downy mildew, white rust, damping-off, cotton rot, blight, late blight, root rot, damping-off, Verticillium wilt, black spot, gray mold, brown spot, black spot, leaf spot, early blight, ring rot, leaf blight, stem base rot, rust, smut, sheath blight, powdery mildew, sclerotinia, black spot, clubroot. In another preferred embodiment, the fungicide prevents and controls the following diseases: anthracnose, downy mildew, gray mold, rust, sheath blight, powdery mildew.

[0046] In another preferred embodiment, the fungicide controls the following diseases: cucumber anthracnose, cucumber downy mildew, rape downy mildew, soybean downy mildew, beet downy mildew, sugarcane downy mildew, tobacco downy mildew, pea downy mildew, loofah downy mildew, wax gourd downy mildew, melon downy mildew, cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew, cotton boll black gray mold, hemp gray mold, tomato gray mold, pepper gray mold, bean gray mold, leek gray mold, kiwi gray mold, strawberry gray mold disease, cucumber gray mold, wheat stripe rust, wheat stem rust, wheat leaf rust, flower rust, sunflower rust, sugarcane rust, leek rust, onion rust, chestnut rust, soybean rust, corn rust, wheat sheath blight, rice sheath blight, 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, wax gourd powdery mildew, melon powdery mildew, grape powdery mildew, and broad bean powdery mildew.

[0047] The fourth aspect of the present invention provides a method for controlling plant fungal diseases, comprising the step of applying to plants a compound as described in any one of claims 1 to 5, its optical isomers, cis-trans isomers or its pesticide-acceptable salts, or a pesticide composition as described in claim 6.

[0048] In another preferred embodiment, the fungal disease is selected from: anthracnose, downy mildew, white rust, damping-off, cotton rot, blight, late blight, root rot, damping-off, verticillium wilt, black spot, gray mold, brown spot, black spot, leaf spot, early blight, ring rot, leaf blight, stem base rot, rust, smut, sheath blight, powdery mildew, sclerotinia, black spot, and clubroot.

[0049] The invention synthesizes analogs containing Sydney ketone or Sydney ketimine, and the preparation method is simple and easy, the operation is simple, the product purification is easy, the cost is low, and the stability is improved. The analogs containing Sydney ketone or Sydney ketimine of the invention have obvious antibacterial activity as confirmed by experiments, and are used for preventing and controlling diseases of crops, fruit trees, Chinese herbal medicines and flowers.

[0050] It should be understood that within the scope of the present invention, the above-mentioned technical features of the present invention and the technical features specifically described below (such as embodiments) can be combined with each other to form a new or preferred technical solution. Each feature disclosed in the specification can be replaced by any alternative feature that provides the same, equal or similar purpose. Due to space limitations, they will not be described one by one here. DETAILED DESCRIPTION

[0051] After extensive and in-depth research, the inventors of the present application have developed a series of analogues containing Sydney ketone or Sydney ketimine structures, which have multiple antibacterial activities, not only have obvious inhibitory effects on cucumber downy mildew and cucumber anthracnose, but also have good inhibitory activity on wheat powdery mildew, corn rust, rice sheath blight, and cucumber gray mold, and can be used as pesticides in agricultural production.

[0052] the term

[0053] In the present invention, the term "C1-C8" refers to having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, and so on. "4-8 membered" refers to having 4-8 ring atoms, and so on.

[0054] The term "C1-C8 alkyl" refers to a straight or branched chain alkyl group having 1 to 8 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl or the like.

[0055] The term "C2-C6 alkenyl" refers to a straight or branched alkenyl group having 2 to 6 carbon atoms, such as vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl or the like.

[0056] The term "C2-C6 alkynyl" refers to a straight chain or branched chain alkynyl group having 2 to 6 carbon atoms, such as ethynyl, propynyl or the like.

[0057] The term "C3-C6 cycloalkyl" refers to a cyclic alkyl group having 3 to 6 carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or the like.

[0058] The term "C5-C7 cycloalkenyl" refers to a cyclic alkenyl group having 5 to 7 carbon atoms and having one or more double bonds, such as cyclopentenyl, cyclohexenyl, cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl or the like.

[0059] The term "C1-C6 alkoxy" refers to a straight or branched alkoxy group having 1 to 6 carbon atoms, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy or the like.

[0060] The term "halogen" refers to fluorine, chlorine, bromine or iodine. The term "halogenated" refers to a group substituted by the same or different one or more halogen atoms mentioned above, for example trifluoromethyl, pentafluoroethyl, heptafluoroisopropyl or the like.

[0061] The term "alkyl" refers to an alkane molecule with one hydrogen atom missing.

[0062] The term "alkylene" refers to an alkane molecule minus two hydrogen atoms.

[0063] The term "aryl" refers to a hydrocarbon moiety containing one or more aromatic rings. For example, the term "C6-C 10 The term "aryl" refers to an aromatic ring group having 6 to 10 carbon atoms and containing no heteroatoms in the ring, such as phenyl, naphthyl, etc.

[0064] The term "heteroaryl" refers to a heteroaromatic system containing 1 to 4 heteroatoms, including nitrogen, oxygen and S(O)r (wherein r is an integer of 0, 1, or 2). For example, a 4-8 membered heteroaryl refers to a heteroaromatic system containing 4 to 8 ring atoms, and a 4-10 membered heteroaryl refers to a heteroaromatic system containing 4 to 10 ring atoms, including but not limited to pyrrolyl, furanyl, thienyl, pyrazolyl, thiazolyl, imidazolyl, oxazolyl, isoxazolyl, pyridinyl, pyranyl, pyridazinyl, pyrimidinyl, pyrazinyl, benzimidazolyl, triazolyl, and the like.

[0065] The term "ring system" refers to a carbocyclic or heterocyclic ring.

[0066] The term "heterocyclic group" refers to a cyclic group containing at least one ring heteroatom (e.g., N, O, or S). Typically, the heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens, and / or no more than 2 sulfurs. Unless otherwise indicated, the heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. Examples of heterocyclic groups include, but are not limited to, morpholinyl, hexahydroisoindolyl, tetrahydrofuranyl, tetrahydropyrrolyl, etc.

[0067] Bactericidal activity of the active substance of the present invention

[0068] The term "active substance of the present invention" or "active compound of the present invention" refers to a compound of the structure shown in general formula (I) or a pesticide-acceptable salt thereof. The heterocyclic structure containing N and O has significant fungicidal activity, a broad fungicidal spectrum and strong stability.

[0069] The term "pesticide acceptable salt" means that the anion of the salt is known and acceptable when forming a pharmaceutically acceptable salt of a fungicide. Preferably, the salt is water-soluble. Suitable acid addition salts formed by the compound of formula (I) include salts formed by inorganic acids, such as hydrochlorides, phosphates, sulfates, nitrates; and salts formed by organic acids, such as acetates, benzoates, etc.

[0070] The compounds involved in the present invention have good control effects on cucumber downy mildew, cucumber anthracnose, wheat powdery mildew, corn rust, rice sheath blight and cucumber gray mold.

[0071] Bactericide composition containing the active substance of the present invention

[0072] The active substances of the present invention can be prepared into fungicide compositions by conventional methods. These active compounds can be made into conventional formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active substances, microcapsules in polymers, coating compounds for seeds, and formulations used with combustion devices, such as fumigation cartridges, fumigation pots and fumigation trays, and ULV cold mist and hot mist formulations.

[0073] These preparations can be produced in a known manner, for example by mixing the active compound with an extender, i.e. a liquid, liquefied gas or solid diluent or carrier and optionally a surfactant, i.e. an emulsifier and / or dispersant and / or foam former. For example, when water is used as the extender, an organic solvent can also be used as an auxiliary agent.

[0074] When a liquid solvent is used as a diluent or carrier, it is basically suitable, such as: aromatic hydrocarbons, for example xylene, toluene or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons, for example chlorobenzene, vinyl chloride or methylene chloride; aliphatic hydrocarbons, for example cyclohexane or paraffin, for example mineral oil fractions; alcohols, for example ethanol or ethylene glycol and their ethers and lipids; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; or less commonly used polar solvents, for example dimethylformamide, dimethyl sulfoxide and water.

[0075] A diluent or carrier for liquefied gas refers to a liquid that will become a gas at normal temperature and pressure, such as an aerosol propellant, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.

[0076] Solid carriers can be ground natural minerals, such as kaolin, clay, talc, quartz, atavistic clay, montmorillonite, or diatomaceous earth; and ground synthetic minerals, such as highly dispersed silicic acid, alumina and silicates. Solid carriers for particles are ground and classified natural zircons, such as calcite, marble, pumice, sepiolite, dolomite, inorganic and organic coarse powder synthetic particles, and organic materials such as sawdust, coconut shells, corn cobs and tobacco stem particles, etc.

[0077] Nonionic and anionic emulsifiers can be used as emulsifiers and / or foam formers. For example, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and albumin hydrolysates. Dispersants include lignin sulfite waste liquor and methylcellulose.

[0078] Binders such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or emulsions, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, may be used in the formulation.

[0079] Colorants 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. can be used.

[0080] The active compounds of the present invention may be mixed with other active compounds in their commercial preparations or in the use formulations prepared from these preparations, and these other active compounds are insecticides, bactericides, fungicides, herbicides, growth control agents, etc. Insecticides include, for example, phosphates, carbamates, chlorinated hydrocarbons, and substances produced by microorganisms, such as avermectin, etc., and fungicides include strobilurins, amides, triazoles, etc.

[0081] In addition, the active compounds of the present invention may also be mixed with synergists in their commercial preparations or dosage forms prepared from these preparations. These synergists are compounds that enhance the effects of the active compounds. Since the active compounds themselves are active, it is not necessary to add synergists.

[0082] These preparations 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 compound of the present invention, based on the total weight of the fungicide composition. The concentration of the active compound in the commercial preparation or use formulation can vary over a wide range. The concentration of the active compound in the use formulation can be from 0.0000001-100% (g / v), preferably between 0.0001 and 1% (g / v).

[0083] Preparation method of the compound of the present invention

[0084] The compound of the general formula (I) of the present invention can be prepared by the following method, however, the conditions of the method, such as reactants, solvents, bases, the amount of the compounds used, reaction temperature, reaction time, etc. are not limited to the following explanation. The compound of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in this specification or known in the art, and such combination can be easily performed by a person skilled in the art to which the present invention belongs.

[0085] The present invention is further described below in conjunction with specific examples. It should be understood that these examples are only used to illustrate the present invention and are not intended to limit the scope of the present invention. The experimental methods in the following examples that do not specify specific conditions are usually carried out under conventional conditions or under conditions recommended by the manufacturer. The materials described can be obtained from public commercial sources unless otherwise specified. Unless otherwise specified, percentages and parts are calculated by weight.

[0086] Example 1: Preparation of 3-(2-methyl-4-heptafluoroisopropylbenzyl)sydney ketone

[0087] 1.1 Preparation of 2-(2-methyl-4-heptafluoroisopropylbenzyl)aminoacetic acid

[0088]

[0089] Dissolve 10 mmol of 4-heptafluoroisopropylbenzylamine in 80 ml of acetone, add 10 mmol of chloroacetic acid and 50 g of anhydrous potassium carbonate. Heat under reflux overnight and track the reaction by TLC. Filter the reaction solution, evaporate the filtrate, and obtain 2-(2-methyl-4-heptafluoroisopropylphenyl)aminoacetic acid (yield 72%, light yellow liquid) by column chromatography. 1 H NMR(400MHz, CDCl3 d)δ:7.36(m,2H),7.21(m,2H),3.79(s,2H),3.49(s,2H); HRMS(ESI)m / z[M+H] + C 12 H 11 F7NO2, calculated value: 334.0415, measured value: 334.0419.

[0090] 1.2 Preparation of 3-(4-heptafluoroisopropylbenzyl)sydney ketone

[0091]

[0092] 13.81mmol 2-(2-methyl-4-heptafluoroisopropylphenyl)aminoacetic acid was dissolved in 150ml anhydrous tetrahydrofuran, and 20.71mmol tert-butyl nitrite was added dropwise under argon protection at 0°C. The reaction gradually returned to room temperature within 1 hour, and the reaction was tracked by TLC. After the reaction was completed, 15mmol of trifluoroacetic anhydride was added, stirred at room temperature for 1 hour, and the reaction was tracked by TLC. After the reaction was completed, ethyl acetate / water was added to quench the reaction, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified by column chromatography to obtain 3-(2-methyl-4-heptafluoroisopropylphenyl) Sydney ketone (yield 73%, light yellow solid). 1H NMR(400MHz, CDCl3 d)δ:7.76(s,1H),7.28(m,2H),7.20(m,2H),2.29(s,2H); HRMS(ESI)m / z[M+H] + C 12 H8F7N2O2, calculated value: 345.1928, found value: 345.1930.

[0093] Example 2: Preparation of 3-(4-trifluoromethylbenzyl)sydney ketone

[0094] 2.1 Preparation of 4-(trifluoromethylbenzyl)aminoacetic acid

[0095]

[0096] Dissolve 10 mmol of 4-trifluoromethylbenzylamine in 80 ml of acetone, add 10 mmol of chloroacetic acid and 50 g of anhydrous potassium carbonate. Heat under reflux overnight and track the reaction by TLC. Filter the reaction solution, evaporate the filtrate, and obtain 4-(trifluoromethylbenzyl)aminoacetic acid (yield 75%, light yellow liquid) by column chromatography. 1 H NMR(400MHz, CDCl3 d)δ:12.59(s,1H),7.49(m,2H),7.15(m,2H),4.10(s,1H),3.9(s,2H),3.29(s,2H); HRMS(ESI)m / z[M+H] + C 10 H 11 F3NO2, calculated value: 234.1907, measured value: 234.1908.

[0097] 2.2 Preparation of 3-(4-trifluoromethylbenzyl)sydney ketone

[0098]

[0099] 13.81mmol 4-(trifluoromethylbenzyl)aminoacetic acid was dissolved in 150ml anhydrous tetrahydrofuran, and 20.71mmol tert-butyl nitrite was added dropwise at 0°C under argon protection. The reaction gradually returned to room temperature within 1 hour, and the reaction was tracked by TLC. After the reaction was completed, 15mmol trifluoroacetic anhydride was added, stirred at room temperature for 1 hour, and the reaction was tracked by TLC. After the reaction was completed, ethyl acetate / water was added to quench the reaction, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified by column chromatography to obtain 3-(4-trifluoromethylbenzyl)sydney ketone (yield 65%, light yellow solid). 1H NMR(400MHz, CDCl3 d)δ:7.76(s,1H),7.45(m,2H),7.10(m,2H),2.29(s,2H); HRMS(ESI)m / z[M+H] + C 10 H8F3N2O2, calculated value: 245.1752, found value: 245.1730.

[0100] Example 3: 3-(3-trifluoromethylbenzyl)sydney ketone

[0101] 3.1 Preparation of 3-(trifluoromethylbenzyl)aminoacetic acid

[0102]

[0103] Dissolve 10 mmol of 3-trifluoromethylbenzylamine in 80 ml of acetone, add 10 mmol of chloroacetic acid and 50 g of anhydrous potassium carbonate. Heat under reflux overnight and track the reaction by TLC. Filter the reaction solution, evaporate the filtrate, and obtain 3-(trifluoromethylbenzyl)aminoacetic acid (yield 76%, light yellow liquid) by column chromatography. 1 H NMR(400MHz, CDCl3 d)δ:13.00(s,1H),7.45-7.53(m,3H),7.28(m,1H),4.12(s,1H),3.80(s,2H),3.19(s,2H); HRMS(ESI)m / z[M+H] + C 10 H 11 F3NO2, calculated value: 234.1907, measured value: 234.1909.

[0104] 3.2 Preparation of 3-(3-trifluoromethylbenzyl)sydney ketone

[0105]

[0106] 13.81mmol 3-(trifluoromethylbenzyl)aminoacetic acid was dissolved in 150ml anhydrous tetrahydrofuran, and 20.71mmol tert-butyl nitrite was added dropwise at 0°C under argon protection. The reaction gradually returned to room temperature within 1 hour, and the reaction was tracked by TLC. After the reaction was completed, 15mmol trifluoroacetic anhydride was added, stirred at room temperature for 1 hour, and the reaction was tracked by TLC. After the reaction was completed, ethyl acetate / water was added to quench the reaction, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified by column chromatography to obtain 3-(3-trifluoromethylbenzyl)sydney ketone (yield 67%, light yellow solid). 1H NMR(400MHz, CDCl3 d)δ:7.76(s,1H),7.47(s,1H),7.45(s,1H),7.43(m,1H),7.41(m,1H),2.29(s,2H); HRMS(ESI)m / z[M+H] + C 10 H8F3N2O2, calculated value: 245.1752, found value: 245.1731.

[0107] Example 4: Preparation of 3-(5-chlorofuran-2-methyl)sydney ketone

[0108] 4.1 Preparation of 2-(5-chlorofuranylmethylamino)-2-phenylacetic acid

[0109]

[0110] Dissolve 10 mmol of 2-(5-chlorofuranyl)methylamine in 50 ml of ethyl acetate, add 10 mmol of α-bromophenylacetic acid and 10 mmol of triethylamine. Heat under reflux overnight and track the reaction by TLC. After the reaction, add water, extract with ethyl acetate, then wash with saturated sodium chloride solution, separate the organic phase, and after rotary evaporation, obtain 2-(5-chlorofuranylmethylamino)-2-phenylacetic acid (yield 60%, light red liquid) by column chromatography. 1 H NMR(400MHz, CDCl3 d)δ:12.69(s,1H),6.39(m,1H),6.29(m,1H),4.16(s,1H),4.92(s,1H),3.66(s,1H),3.49(s,2H); HRMS(ESI)m / z[M+H] + C7H9NClO3, calculated value: 190.0602, found value: 190.0603.

[0111] 4.2 Preparation of 3-(5-chlorofuran-2-methyl)sydney ketone

[0112]

[0113] The synthesis of the target compound was similar to step 1.2 of Example 1, except that 2-(5-chlorofuranylmethylamino)-2-phenylacetic acid was used instead of 2-(2-methyl-4-heptafluoroisopropylphenyl)aminoacetic acid. (yield 66%, light yellow solid). 1 HNMR(400MHz, CDCl3 d)δ:7.76(m,1H),6.33(m,1H),6.10(m,1H),2.10(s,2H); HRMS(ESI)m / z[M+H] +C7H6N2ClO3, calculated value: 201.1452, found value: 201.1420.

[0114] Example 5: Preparation of 3-(pyridine-4-methyl)-4-phenylsydney ketone

[0115] 5.1 Preparation of 2-phenyl-2-(4-pyridylmethylamino)acetic acid

[0116]

[0117] Dissolve 20 mmol of 4-methylaminopyridine in 50 ml of ether, add 10 mmol of α-bromophenylacetic acid, heat under reflux overnight, and track the reaction by TLC. After the reaction, add water and filter to obtain: 2-phenyl-2-(4-pyridylmethylamino)acetic acid (yield 80%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:12.69(s,1H),8.55(m,2H),7.25-7.35(m,6H),5.01(s,1H),4.65(s,1H),4.20(s,2H); HRMS(ESI)m / z[M+H] + C 14 H 15 N2O2, calculated value: 243.2803, measured value: 243.2805.

[0118] 5.2 Preparation of 3-(pyridine-4-methyl)-4-phenylsydney ketone

[0119]

[0120] The synthesis of the target compound was similar to step 1.2 of Example 1, except that 2-phenyl-2-(4-pyridylmethylamino)acetic acid was used instead of 2-(2-methyl-4-heptafluoroisopropylphenyl)aminoacetic acid. (Yield 70%, light yellow solid). 1 HNMR(400MHz, CDCl3 d)δ:8.53(m,2H),7.68(m,2H),7.55(m,1H),7.53(m,2H),7.22(m,2H)2.29(s,2H); HRMS(ESI)m / z[M+H] + C 14 H 12 N3O2, calculated value: 254.2612, measured value: 254.2622.

[0121] Example 6: Preparation of 3-(4-trifluoromethoxybenzyl)-4-phenylsydney ketone

[0122] 6.1 Preparation of 2-(4-trifluoromethoxybenzylamino)-2-phenylacetic acid

[0123]

[0124] Dissolve 20 mmol of p-trifluoromethoxybenzylamine in 50 ml of ether, add 10 mmol of α-bromophenylacetic acid, heat under reflux overnight, and track the reaction by TLC. After the reaction, add water and filter to obtain: 2-(4-trifluoromethoxybenzylamino)-2-phenylacetic acid (yield 85%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:12.65(s,1H),7.25-7.33(m,5H),7.13(m,2H),6.89(m,2H),4.92(s,1H),4.70(s,1H),3.80(s,2H); HRMS(ESI)m / z[M+H] + C 16 H 13 NO3F3, calculated value: 326.1314, measured value: 326.1312.

[0125] 6.2 Preparation of 3-(4-trifluoromethoxybenzyl)-4-phenylsydney ketone

[0126]

[0127] 13.81mmol 2-(4-trifluoromethoxybenzylamino)-2-phenylacetic acid was dissolved in 150ml anhydrous tetrahydrofuran, and 20.71mmol tert-butyl nitrite was added dropwise at 0°C under argon protection. The reaction gradually returned to room temperature within 1 hour, and the reaction was tracked by TLC. After the reaction was completed, 15mmol trifluoroacetic anhydride was added, stirred at room temperature for 1 hour, and the reaction was tracked by TLC. After the reaction was completed, ethyl acetate / water was added to quench the reaction, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with saturated sodium chloride, dried with anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified by column chromatography to obtain 3-trifluoromethoxybenzyl-4-phenylsydney ketone (yield 70%, light yellow solid). 1 H NMR(400MHz, CDCl3 d)δ:7.68(m,1H),7.56-7.58(m,4H),7.10(m,2H),7.01(m,2H),2.29(s,2H); HRMS(ESI)m / z[M+H] + C 16 H 11 N2O3F3, calculated value: 337.1102, found value: 337.1101.

[0128] Example 7: Preparation of 3-trifluoromethylbenzyl-4-trifluoromethylphenylsydney ketone

[0129] 7.1 Preparation of 2-bromo-2-(3-trifluoromethylphenyl)acetic acid

[0130]

[0131] 5 mmol of NBS and 0.2 mmol of dibenzoyl peroxide were dissolved in 5 ml of carbon tetrachloride, and the mixture was heated to reflux, and then 5 mmol of 2-trifluoromethylphenylacetic acid dissolved in 3 ml of carbon tetrachloride was added. The reaction was heated to reflux for 6 hours, and the reaction was tracked by TLC. After the reaction was completed, it was allowed to stand and cool, filtered, and the filtrate was washed with sodium bicarbonate solution to separate the organic phase. After rotary evaporation, it was subjected to column chromatography to obtain: 2-bromo-2-(3-trifluoromethylphenyl)acetic acid (yield 70%, light yellow liquid). 1 H NMR(400MHz, CDCl3 d)δ:12.75(s,1H),7.45-7.51(m,3H),7.21(m,1H),5.90(s,1H); HRMS(ESI)m / z[M+H] + C9H7BrF3O2, calculated value: 284.0416, found value: 284.0415.

[0132] 7.2 Preparation of 2-((4-trifluoromethylbenzyl)amino)-2-(3-trifluoromethylphenyl)acetic acid

[0133]

[0134] The synthesis of the target compound was similar to step 5.1 of Example 5, except that 2-bromo-2-(3-trifluoromethylphenyl)acetic acid was used instead of α-bromophenylacetic acid, and 4-trifluoromethylbenzylamine was used instead of 4-methylaminopyridine. (yield 80%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:12.73(s,1H),7.45-7.51(m,5H),7.21(m,1H),7.15(m,2H),4.90(s,1H),4.80(s,1H),3.80(s,2H); HRMS(ESI)m / z[M+H] + C 17 H 14 NF6O2, calculated value: 378.2916, measured value: 378.2954.

[0135] 7.3 Preparation of 3-trifluoromethylbenzyl-4-trifluoromethylphenylsydney ketone

[0136]

[0137] The synthesis of the target compound was similar to step 1.2 of Example 1, except that 2-((4-trifluoromethylbenzyl)amino)-2-(3-trifluoromethylphenyl)acetic acid was used instead of 2-(2-methyl-4-heptafluoroisopropylphenyl)aminoacetic acid. (yield 59%, light yellow solid). 1 H NMR(400MHz, CDCl3 d)δ:8.09(m,1H),7.78(m,2H),7.65(m,2H),7.53(m,1H),7.22(m,2H)2.25(s,2H); HRMS(ESI)m / z[M+H] + C 17 H 11 F6N2O2, calculated value: 389.2712, found value: 389.2716.

[0138] Example 8: Preparation of 3-trifluoromethylbenzyl-4-(3,5-dichlorophenyl)sydney ketone

[0139] 8.1 Preparation of 2-bromo-2-(3,5-dichlorophenyl)acetic acid

[0140]

[0141] Dissolve 5mmol of NBS and 0.2mmol of dibenzoyl peroxide in 5ml of carbon tetrachloride, heat the mixture under reflux, and then add 5mmol of 3,5-dichlorophenylacetic acid dissolved in 3ml of carbon tetrachloride. The reaction is heated under reflux for 6 hours, and the reaction is tracked by TLC. After the reaction is completed, let it stand and cool, filter, wash the filtrate with sodium bicarbonate solution, separate the organic phase, and after rotary evaporation, obtain: 2-bromo-2-(3,5-dichlorophenyl)acetic acid (yield 75%, light yellow liquid) by column chromatography. 1 H NMR(400MHz, CDCl3 d)δ:12.73(s,1H),7.51(s,1H),7.31(s,2H),5.92(s,1H); HRMS(ESI)m / z[M+H] + C8H6BrCl2O2, calculated value: 284.8842, found value: 284.8843.

[0142] 8.2 Preparation of 2-((4-trifluoromethylbenzyl)amino)-2-(3,5-dichlorophenyl)acetic acid

[0143]

[0144] The synthesis of the target compound was similar to step 5.1 of Example 5, except that 2-bromo-2-(3,5-dichlorophenyl)acetic acid was used instead of α-bromophenylacetic acid, and 4-trifluoromethylbenzylamine was used instead of 4-methylaminopyridine. (yield 82%, white solid). 1 HNMR(400MHz, CDCl3 d)δ:12.72(s,1H),7.55-7.58(m,3H),7.34(s,2H),7.20(m,2H),5.00(s,1H),4.82(s,1H).3.80(s,2H); HRMS(ESI)m / z[M+H] + C 16 H 13 Cl2NF3O2, calculated value: 379.1725, found value: 379.1735.

[0145] 8.3 Preparation of 3-trifluoromethylbenzyl-4-(3,5-dichlorophenyl)sydney ketone

[0146]

[0147] The synthesis of the target compound was similar to step 1.2 of Example 1, except that 2-((4-trifluoromethylbenzyl)amino)-2-(3,5-dichlorophenyl)acetic acid was used instead of 2-(2-methyl-4-heptafluoroisopropylphenyl)aminoacetic acid. (yield 63%, light yellow solid). 1 H NMR(400MHz, CDCl3 d)δ:7.89(m,2H),7.78(m,1H),7.65(m,2H),7.53(m,2H),2.28(s,2H); HRMS(ESI)m / z[M+H] + C 16 H 10 Cl2F3N2O2, calculated value: 390.1622, found value: 390.1631.

[0148] Example 9: Preparation of 3-thienylmethyl-4-phenylsydney ketone

[0149] 9.1 Preparation of 2-phenyl-2-(2-thienylmethylamino)acetic acid

[0150]

[0151] The synthesis of the target compound was similar to step 5.1 of Example 5, except that 2-aminomethylthiophene was used instead of 4-methylaminopyridine (yield 92%, white solid). 1H NMR (400MHz, CDCl3 d)δ:12.72(s,1H),7.27-7.31(m,5H),7.44(m,1H),7.10(m,1H),7.00(m,1H),5.00(s,1H),4.82(s,1H).3.80(s,2H); HRMS(ESI)m / z[M+H] + C 13 H 14 NSO2, calculated value: 248.3112, measured value: 248.3115.

[0152] 9.2 Preparation of 3-thienylmethyl-4-phenylsydney ketone

[0153]

[0154] The synthesis of the target compound was similar to step 1.2 of Example 1, except that 2-phenyl-2-(2-thienylmethylamino)acetic acid was used instead of 2-(2-methyl-4-heptafluoroisopropylphenyl)aminoacetic acid. (yield 63%, light yellow solid). 1 HNMR(400MHz, CDCl3 d)δ:7.69(m,2H),7.56(m,1H),7.51(m,2H),7.33(m,1H),6.95(m,1H),6.82(m,1H),2.30(s,2H); HRMS(ESI)m / z[M+H] + C 13 H 11 SN2O2, calculated value: 259.3012, found value: 259.3022.

[0155] Example 10: Preparation of 3-cyclopropylmethyl-4-phenylsydney ketone

[0156] 10.1 Preparation of 2-phenyl-2-(cyclopropylmethylamino)acetic acid

[0157]

[0158] The synthesis of the target compound was similar to step 5.1 of Example 5, except that cyclopropylmethylamine was used instead of 4-methylaminopyridine (yield 81%, white solid). 1 H NMR (400MHz, CDCl3 d)δ:12.72(s,1H),7.27-7.31(m,5H),4.82(s,1H),4.78(s,1H).2.44(s,2H),1.02(m,1H),0.41(m,2H),0.15(m,2H); HRMS(ESI)m / z[M+H] + C12 H 16 NO2, calculated value: 206.2612, measured value: 206.2615.

[0159] 10.2 Preparation of 3-cyclopropylmethyl-4-phenylsydneyketone

[0160]

[0161] The synthesis of the target compound is similar to step 1.2 of Example 1, except that 2-phenyl-2-(cyclopropylmethylamino)acetic acid is used instead of 2-(2-methyl-4-heptafluoroisopropylphenyl)aminoacetic acid. (yield 50%, light yellow solid). 1 HNMR(400MHz, CDCl3 d)δ:7.69(m,2H),7.56(m,1H),7.51(m,2H),1.03(m,1H),0.92(m,2H),0.40(m,2H),0.16(m,2H); HRMS(ESI)m / z[M+H] + C 12 H 13 N2O2, calculated value: 217.2412, measured value: 217.2435.

[0162] Example 11: Preparation of N-Boc-3-heptylsydneyketimine

[0163] 11.1 Preparation of 2-heptylaminoacetonitrile

[0164]

[0165] 92.29mmol of heptylamine and 101.79mmol of triethylamine were added to 33.8ml of ethyl acetate, and the reaction system was kept below 5°C. 92.54mmol of bromoacetonitrile was added dropwise to the reaction system over 2 hours. After the addition was completed, the reaction was stirred at room temperature for 3 hours, and the reaction was tracked by TLC. After the reaction was completed, 33.8ml of water was added. The organic phase was separated, washed with 10% sodium chloride solution, the solvent was removed by suspension, and purified by column chromatography to obtain 2-(heptylamine)acetonitrile (yield 58%, colorless liquid). 1 H NMR(400MHz, CDCl3 d1)δ:3.81(s,2H),3.31(s,1H),2.46(m,2H),1.41(m,2H),1.31-1.36(m,8H),0.92(m,3H); HRMS(ESI)m / z[M+H] + C9H 19 N2, calculated value: 155.2642, measured value: 155.2641.

[0166] 11.2 Preparation of 3-heptylsydneyketimine hydrochloride

[0167]

[0168] Dissolve 5mmol 2-(heptylamine)acetonitrile in 5ml ether, add 7.5mmol tert-butyl nitrite, and track the reaction by TLC. After the reaction is completed, dry hydrogen chloride gas is passed into the reaction solution under ice bath conditions, and the reaction is tracked by TLC. After the reaction is completed, Sydney ketimine hydrochloride will crystallize out, and after filtering, washing with petroleum ether / ether (1:1), recrystallization in isopropanol or ethanol gives the product (yield 71%, white solid). 1 H NMR(400MHz,D2O)δ:9.95(br.s,2H),7.71(s,1H),1.41(m,2H),1.33-1.38(m,8H),0.92(m,2H),0.82(m,3H); HRMS(ESI)m / z[M+H] + C9H 19 N3O, calculated value: 185.2603, measured value: 185.2604.

[0169] 11.3 Preparation of N-Boc-3-heptylsydneyketimine

[0170]

[0171] 25mmol 3-heptyl sydney ketimine hydrochloride, 75mmol di-tert-butyl dicarbonate, 1.25mmol DMAP, dissolved in 100ml chloroform, refluxed for 2-3 hours, until the reaction stopped releasing gas. After cooling to room temperature, 20ml 5% sodium bicarbonate solution was added, the aqueous phase was separated and extracted with chloroform, the organic phases were combined, dried over anhydrous sodium sulfate, and then the solvent was suspended. The product was recrystallized from isopropanol / petroleum ether (yield 65%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:7.72(s,1H),1.48(s,9H),1.43(m,2H),1.32-1.37(m,8H),0.90(m,2H),0.81(m,3H); HRMS(ESI)m / z[M+H] + C 14 H 26 N3O3, calculated value: 284.1903, measured value: 284.1904.

[0172] Example 12: Preparation of N(6)-Boc-3-p-fluorobenzyl-4-phenylsydneyketimine

[0173] 12.1 Preparation of α-bromophenylacetonitrile

[0174]

[0175] 5mmol of NBS and 0.2mmol of dibenzoyl peroxide were dissolved in 5ml of carbon tetrachloride, and the mixture was heated to reflux, and then 5mmol of benzyl cyanide dissolved in 3ml of carbon tetrachloride was added. The reaction was heated to reflux for 6 hours, and the reaction was tracked by TLC. After the reaction was completed, it was allowed to stand and cool, filtered, and the filtrate was washed with sodium bicarbonate solution to separate the organic phase. After rotary evaporation, it was subjected to column chromatography to obtain: α-bromobenzeneacetonitrile (yield 75%, light yellow liquid). 1 H NMR(400MHz, CDCl3d)δ:7.25-7.35(m,5H),5.97(s,1H); HRMS(ESI)m / z[M+H] + C8H7BrN, calculated value: 196.9703, found value: 196.9705.

[0176] 12.2 Preparation of 2-(4-fluorobenzylamino)-2-phenylacetonitrile

[0177]

[0178] Dissolve 10 mmol of p-fluorobenzylamine in 50 ml of ethyl acetate, add 10 mmol of α-bromobenzyl acetonitrile and 10 mmol of triethylamine. Stir the reaction overnight and track the reaction by TLC. After the reaction, add water, extract with ethyl acetate, then wash with saturated sodium chloride solution, separate the organic phase, and after rotary evaporation, obtain 2-(4-fluorobenzylamino)-2-benzyl acetonitrile (yield 70%, yellow liquid) by column chromatography. 1 H NMR(400MHz, CDCl3 d)δ:7.62(m,2H),7.41-7.44(m,5H),7.07(m,2H),5.01(s,1H),4.93(s,1H),3.78(s,2H); HRMS(ESI)m / z[M+H] + C 15 H 14 FN2, calculated value: 241.1101, measured value: 241.1102.

[0179] 12.3 Preparation of 3-(4-fluorobenzyl)-4-phenylsydneyketimine hydrochloride

[0180]

[0181] 5mmol 2-(4-fluorobenzylamino)-2-phenylacetonitrile was dissolved in 5ml ether, 7.5mmol tert-butyl nitrite was added, and the reaction was tracked by TLC. After the reaction was completed, dry hydrogen chloride gas was passed into the reaction solution under ice bath conditions, and the reaction was tracked by TLC. After the reaction was completed, Sydney ketimine hydrochloride was crystallized and precipitated. After filtering, washing with petroleum ether / ether (1:1), and recrystallization in isopropanol or ethanol gave the product (yield 71%, white solid). 1 H NMR(400MHz,D2O)δ:9.95(br.s,2H),7.75(m,2H),7.69(m,2H),7.59-7.61(m,3H),7.18(m,2H),2.28(s,2H); HRMS(ESI)m / z[M+H] + C 15 H 14 FN3O, calculated value: 271.0721, measured value: 271.0720.

[0182] 12.4 Preparation of N(6)-Boc-3-(p-fluorobenzyl)-4-phenylsydneyketimine

[0183]

[0184] 25mmol 3-p-fluorobenzyl-4-phenyl sydney ketimine hydrochloride, 75mmol di-tert-butyl dicarbonate, 1.25mmol DMAP, dissolved in 100ml chloroform, refluxed for 2-3 hours until the reaction stops and the gas is released. After cooling to room temperature, 20ml 5% sodium bicarbonate solution is added, the aqueous phase is separated and extracted with chloroform, the organic phases are combined, dried over anhydrous sodium sulfate, and then the solvent is suspended. The product is recrystallized from isopropanol / petroleum ether (yield 65%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:7.72(m,2H),7.68(m,2H),7.61(m,2H),7.56(m,1H),7.21(m,2H),2.25(m,2H),1.42(m,9H); HRMS(ESI)m / z[M+H] + C 20 H 21 FN3O3, calculated value: 370.1503, found value: 370.1505.

[0185] Example 13: Preparation of N(6)-benzoyl-3-heptylsydneyketimine

[0186]

[0187] 37mmol of 3-heptyl sydney ketimine hydrochloride was added to 70ml of dichloromethane in which 44mmol of benzoyl chloride was dissolved, and then 11.8ml of triethylamine was added, and the mixture was stirred at -20°C for 15 minutes. The mixture was stirred at room temperature for 16 hours, and 50ml of water was added. After separation, the aqueous phase was extracted with dichloromethane, and the organic phases were combined, dried over anhydrous sodium sulfate, and then the solvent was suspended. The product was recrystallized from isopropanol (yield 62%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:7.86(m,2H),7.75(m,1H),7.72(s,1H),7.62(m,2H),1.22-1.27(m,10H),0.90(m,2H),0.81(m,3H); HRMS(ESI)m / z[M+H] + C 16 H 22 N3O2, calculated value: 288.1626, measured value: 288.1627.

[0188] Example 14: Preparation of 3-heptyl-N(6)-p-methylbenzenesulfonyl-sydneyketimine

[0189]

[0190] 92mmol 3-heptyl sydney ketimine hydrochloride was added to 150ml dichloromethane dissolved with 101mmol p-toluenesulfonyl chloride, and then the mixture was added dropwise to 50ml dichloromethane containing 138mmol triethylamine, and then stirred at -20°C for 15 minutes. Stirred at room temperature for 16 hours, filtered to remove insoluble matter, the solution was washed with water and 5% potassium carbonate solution, dried over anhydrous sodium sulfate, and then suspended to dry solvent. The product was recrystallized from isopropanol / petroleum ether (1:1.2) (yield 72%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:7.76(m,3H),7.40(m,2H),2.45(m,3H),1.23-1.30(m,10H),0.95(m,2H),0.86(m,3H); HRMS(ESI)m / z[M+H] + C 16 H 24 N3O3S, calculated value: 338.1534, found value: 338.1533.

[0191] Example 15: Preparation of 3-heptyl-N(6)-trifluoroacetyl-sydneyketimine

[0192]

[0193] 62mmol 3-heptyl sydney ketimine hydrochloride was dissolved in 200ml dichloromethane, 10.4ml trifluoroacetic anhydride was added dropwise to the mixture, 20.5ml triethylamine was added dropwise while stirring at -20°C, and then stirred for 30 minutes. Stirred at room temperature for 16 hours. 150ml water was added, and potassium carbonate was used to neutralize, and the organic phase was separated and dried over anhydrous sodium sulfate, and then the solvent was suspended. The product was recrystallized from isopropanol / petroleum ether (1:2) (yield 82%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:7.76(s,1H),1.25-1.30(m,10H),0.97(m,2H),0.87(m,3H); HRMS(ESI)m / z[M+H] + C 11 H 17 F3N3O2, calculated value: 280.1203, found value: 280.1204.

[0194] Example 16: 3-(3,5-dichlorobenzyl)-N(6)-trifluoroacetyl-sydneyketimine

[0195] 16.1 Preparation of 2-(3,5-dichlorophenyl)aminoacetonitrile

[0196]

[0197] 10 mmol of 3,5-dichlorobenzaldehyde was added to 20 ml of aqueous solution containing 20 mmol of potassium hydroxide and 10 mmol of aminoacetonitrile hydrochloride, and then 20 ml of ethanol was added and stirred for one hour. Then 12 mmol of sodium borohydride was added and stirred at room temperature overnight. Then hydrochloric acid was added to adjust the reaction to acidity, and ethyl acetate was used for extraction, and the organic phase was separated and washed with saturated brine, and the organic phase was separated and dried with anhydrous sodium sulfate, and the solvent was suspended to obtain the product. (yield 80%, yellow solid). 1 H NMR(400MHz, CDCl3 d)δ:7.58(s,1H),7.31(m,2H),4.16(s,1H),3.77(s,2H),3.66(s,2H); HRMS(ESI)m / z[M+H] + C9H9N2Cl2, calculated value: 216.0812, found value: 216.0835.

[0198] 16.2 Preparation of 3,5-dichlorobenzyl sydney ketimine hydrochloride

[0199]

[0200] The synthesis of the target compound was similar to step 11.2 of Example 11, except that 2-(3,5-dichlorophenyl)aminoacetonitrile was used instead of 2-heptylaminoacetonitrile (yield 81%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:9.95(br.s,2H),7.78(s,1H),7.58(s,1H),7.31(m,2H),2.22(s,2H); HRMS(ESI)m / z[M+H] + C9H9N3OCl2, calculated value: 246.0812, found value: 246.0825.

[0201] 16.3 Preparation of 3-(3,5-dichlorobenzyl)-N(6)-trifluoroacetyl-Sydney ketimine

[0202]

[0203] The synthesis of the target compound is similar to that of Example 15, except that 3,5-dichlorobenzyl sydney ketimine hydrochloride is used instead of 3-heptyl sydney ketimine hydrochloride (yield 51%, yellow solid). 1 H NMR(400MHz, CDCl3 d)δ:7.75(s,1H),7.61(s,1H),7.21(m,2H),2.21(s,2H); HRMS(ESI)m / z[M+H] + C 11 H7N3O2Cl2F3, calculated value: 341.0822, found value: 341.0832.

[0204] Example 17: Preparation of 3-(3,5-dichlorobenzyl)-N(6)-dichloroacetyl-sydneyketimine

[0205]

[0206] The synthesis of the target compound is similar to that of Example 15, except that 3,5-dichlorobenzyl sydney ketimine hydrochloride is used instead of 3-heptyl sydney ketimine hydrochloride, and dichloroacetyl chloride is used instead of trifluoroacetic anhydride. (yield 50%, yellow solid). 1 H NMR(400MHz, CDCl3 d)δ:7.75(s,1H),7.61(s,1H),7.21(m,2H),6.33(s,1H),2.21(s,2H); HRMS(ESI)m / z[M+H] + C 11 H8N3O2Cl4, calculated value: 356.0013, found value: 356.0012.

[0207] Example 18: Preparation of 3-(3,5-dichlorobenzyl)-N(6)-bromoacetyl-sydneyketimine

[0208]

[0209] The synthesis of the target compound is similar to that of Example 15, except that 3,5-dichlorobenzyl sydney ketimine hydrochloride is used instead of 3-heptyl sydney ketimine hydrochloride, and bromoacetyl chloride is used instead of trifluoroacetic anhydride. (yield 50%, yellow solid). 1 H NMR(400MHz, CDCl3 d)δ:7.75(s,1H),7.61(s,1H),7.21(m,2H),4.41(s,2H),2.21(s,2H); HRMS(ESI)m / z[M+H] + C 11 H9N3O2Cl2Br, calculated value: 366.0123, found value: 366.0122.

[0210] Example 19: Preparation of N(6)-difluoroacetyl-3-p-fluorobenzyl-4-phenylsydneyketimine

[0211]

[0212] The synthesis of the target compound was similar to that of Example 15, except that 3-p-fluorobenzyl-4-phenylsydney ketimine hydrochloride was used instead of 3-heptylsydney ketimine hydrochloride, and difluoroacetyl chloride was used instead of trifluoroacetic anhydride. (yield 50%, yellow solid). 1 H NMR(400MHz, CDCl3 d)δ:7.75(m,2H),7.69(m,2H),7.61(m,2H),7.51(m,1H),7.21(m,2H),6.02(m,1H),2.23(s,2H); HRMS(ESI)m / z[M+H] + C 17 H 13 N3O2F3, calculated value: 348.3053, found value: 348.3056.

[0213] Example 20: Preparation of 3-heptyl-N(6)-trichloroacetyl-sydneyketimine

[0214]

[0215] The synthesis of the target compound was similar to that of Example 15, except that trichloroacetyl chloride was used instead of trifluoroacetic anhydride (yield 51%, yellow solid). 1H NMR(400MHz, CDCl3 d)δ:7.75(m,2H),1.26-1.30(m,10H),0.98(m,3H),0.86(m,2H); HRMS(ESI)m / z[M+H] + C 11 H 17 N3O2Cl3, calculated value: 329.6212, found value: 329.6216.

[0216] Example 21: Preparation of 3-(3,5-dichlorobenzyl)-N(6)-6-trifluoromethylnicotinoyl-sydneyketimine

[0217]

[0218] The synthesis of the target compound is similar to that of Example 15, except that 3,5-dichlorobenzyl sydney ketimine hydrochloride is used instead of 3-heptyl sydney ketimine hydrochloride, and 6-trifluoromethylnicotinoyl chloride is used instead of trifluoroacetic anhydride. (yield 40%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:8.66(s,1H),8.06(m,1H),7.75(s,1H),7.61(s,1H),7.36(m,1H),7.21(m,2H),2.26(s,2H); HRMS(ESI)m / z[M+H] + C 16 H 10 N4O2Cl2F3, calculated value: 418.0133, found value: 418.0132.

[0219] Example 22: Preparation of 3-(3,5-dichlorobenzyl)-N(6)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-acyl-sydneyketimine

[0220]

[0221] The synthesis of the target compound was similar to that of Example 15, except that 3,5-dichlorobenzyl sydney ketimine hydrochloride was used instead of 3-heptyl sydney ketimine hydrochloride, and 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-yl chloride was used instead of trifluoroacetic anhydride. (yield 48%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:8.70(s,1H),7.75(s,1H),7.61(s,1H),7.21(m,2H),6.45(m,1H),3.82(s,3H),2.26(s,2H); HRMS(ESI)m / z[M+H] + C 15 H12 N5O2Cl2F2, calculated value: 403.0243, found value: 403.0242.

[0222] Example 23: Preparation of 3-(3,5-dichlorobenzyl)-N(6)-phosphoryl dimethyl ester-Sydney ketimine

[0223]

[0224] The synthesis of the target compound is similar to that of Example 15, except that 3,5-dichlorobenzyl sydney ketimine hydrochloride is used instead of 3-heptyl sydney ketimine hydrochloride, and dimethyl phosphorus oxychloride is used instead of trifluoroacetic anhydride. (yield 68%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:7.75(s,1H),7.61(s,1H),7.21(m,2H),3.81(s,6H),2.26(s,2H); HRMS(ESI)m / z[M+H] + C 11 H 13 N3O4PCl2, calculated value: 353.1022, found value: 353.1040.

[0225] Example 24: Preparation of 3-(3,5-dichlorobenzyl)-N(6)-4-morpholineacetyl-sydneyketimine

[0226]

[0227] The synthesis of the target compound is similar to that of Example 15, except that 3,5-dichlorobenzyl sydney ketimine hydrochloride is used instead of 3-heptyl sydney ketimine hydrochloride, and 4-morpholinoacetyl chloride is used instead of trifluoroacetic anhydride. (yield 52%, white solid). 1 H NMR(400MHz, CDCl3 d)δ:7.75(s,1H),7.61(s,1H),7.21(m,2H),3.68(m,4H),3.41(s,2H),2.57(m,4H),2.26(s,2H); HRMS(ESI)m / z[M+H] + C 15 H 17 N4O3Cl2, calculated value: 372.2024, found value: 372.2034.

[0228] The other compounds in Table 1 were prepared using the same synthetic method as in Examples 1-24, with different starting materials.

[0229] Example 25: In vivo antibacterial activity test of the compounds of the present invention

[0230] The host crops are cucumber (variety Xintai Mici), wheat (variety Liaochun No. 10), and corn (variety Jinhuangnuo No. 2).

[0231] Weigh 0.0088g of the new compound and dissolve it in 2ml of acetone, add water containing 0.1% Tween 80 to prepare 20ml of 400mg / L solution. Also prepare 20ml of 6.25mg / L solution of cyazolin and 20ml of 25mg / L solution of azoxystrobin for in vivo screening.

[0232] The two-leaf cucumber seedlings cultured in the greenhouse were used as the experimental host plants for cucumber downy mildew, the two-leaf wheat seedlings were used as the experimental host plants for wheat powdery mildew, and the two-leaf corn seedlings were used as the experimental host plants for corn rust.

[0233] The sprayer type is a three-dimensional crop sprayer, the spray pressure is 1.5kg / cm2, and the spray volume is about 1000L / hm2. The above test materials are treated and then naturally air-dried. Pathogens are inoculated after 24 hours.

[0234] Sporangial suspensions of cucumber downy mildew (5×105 / ml) and corn rust (5×106 / ml) were sprayed on host crops using an inoculator and then transferred to an artificial climate chamber for cultivation (24°C, RH>90, no light). After 24 hours of cultivation, the test materials of cucumber downy mildew and corn rust were transferred to a greenhouse for normal management, and the fungicidal activity of the compounds was investigated 4 days later.

[0235] Powdery mildew spores were shaken onto wheat leaves and cultured in a greenhouse. After 7 days, the fungicidal activity of the compounds was investigated.

[0236] The results were investigated with reference to the "A Manual of Assessment Keys for Plant Diseases" compiled by the American Society of Plant Diseases, expressed on a scale of 100 to 0, with "100" representing disease-free and "0" representing the most severe disease. The control effect (inhibition rate) was calculated using the following formula.

[0237]

[0238]

[0239] Example 26: In vitro antibacterial activity test of the compounds of the present invention

[0240] 0.00625 mg of the new compound was dissolved in 1 ml of dimethyl sulfoxide to prepare a 6.25 mg / L solution. 1 ml of a 25 mg / L solution of the control agent pyraclostrobin was also prepared for in vitro screening.

[0241] Add deionized water to the pre-cultured rice sheath blight and cucumber gray mold fungus plates, gently scrape the spores on the mycelium surface, filter with 3-5 layers of gauze, then put into a centrifuge tube, centrifuge at low speed (1000rpm) for 5 minutes, pour off the supernatant, add deionized water, and centrifuge again. Dilute the precipitated spores with an appropriate amount of deionized water to a spore suspension with about 100 spores under a 100x microscope.

[0242] The prepared drug solution was added to a 96-well culture plate, and each agent was repeated 4 times, with 1 μL per well. Then, the prepared spore suspension was added, with 80 μL added to each well. The rice blast was cultured in a dark incubator at 28°C for 18 hours, and the gray mold was cultured in a dark incubator at 18°C ​​for 18 hours, and then investigated.

[0243] The in vitro screening was performed using the HTS method.

[0244]

[0245]

[0246] Table 1 Antibacterial activity of compounds of formula (I)

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267] Example 27: Composition containing the fungicide compound of the present invention

[0268] (a) Microemulsion

[0269] Prepare the following components in proportion: 5.0% (weight percentage, the same below) of any one of compounds I-1 to I-268 (Table 1); 30.0% polyvinyl pyrrolidone-vinyl acetate copolymer; 30.0% alkyl polyglycoside; 15.0% oleic acid glyceride; 20.0% water.

[0270] (b) Wettable powder

[0271] The following components are prepared in proportion: 65.0% of any one of compounds I-1 to I-268 (Table 1); 2.0% of dodecylphenol polyglycol ether; 4.0% of sodium lignin sulfonate; 6.0% of sodium aluminum silicate; and 23.0% of montmorillonite (calcined).

[0272] (c) Seed treatment agents

[0273] Prepare the following components in proportion: 20.00% of any one of compounds I-1 to I-268 (Table 1); 5.00% polyvinyl pyrrolidone-vinyl acetate copolymer; 5.00% montan acid wax; 1.00% calcium lignin sulfonate; 1.00% polyoxyethylene / polyoxypropylene block copolymer; 2.00% stearyl alcohol (POE 20); 0.20% polysilicone; 0.05% colorant red dye; 65.75% water.

[0274] After reading the above teachings of the present invention, those skilled in the art may make various changes or modifications to the present invention, and these equivalent forms also fall within the scope defined by the claims attached to this application.

Claims

1. A use of a compound having a structure represented by general formula (I) or a pesticide acceptable salt thereof, characterized in that: Used to prevent and control plant fungal diseases or prepare fungicides, In the formula, L is a substituted or unsubstituted phenyl group; wherein the substitution refers to substitution by one or more groups selected from the group consisting of C1-C4 alkyl, halogen, C1-C4 haloalkyl, C3 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl or C1-C4 thioalkyl; Q is a substituted or unsubstituted group selected from the group consisting of -(C1-C4 alkylene)(phenyl) and -(C1-C4 alkylene)(5-6 membered heteroaryl); wherein the substitution refers to substitution by one or more groups selected from the group consisting of C1-C4 alkyl, fluorine, chlorine, bromine, C1-C4 haloalkyl, C3 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyl, nitro, C2-C4 alkynyl and C1-C4 thioalkyl; M is O - , Among them, the fungicide prevents and controls the following diseases: anthracnose, downy mildew, white rust, sudden wilt, cotton rot, late blight, root rot, damping-off, verticillium wilt, gray mold, brown spot, black spot, leaf spot, early blight, ring rot, leaf blight, stem base rot, rust, smut, sheath blight, powdery mildew, sclerotinia, black spot, and clubroot.

2. The use according to claim 1, characterized in that L is a substituted phenyl group; wherein the substitution refers to substitution by one or more groups selected from the group consisting of C1-C4 alkyl, halogen, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy.

3. The use according to claim 1, characterized in that L is a substituted or unsubstituted phenyl group; wherein the substitution refers to substitution by one or more groups selected from the group consisting of fluorine, chlorine, bromine, C1-C4 haloalkyl or C1-C4 haloalkoxy.

4. The use according to claim 1, characterized in that L is phenyl, 5. The use according to claim 1, characterized in that Q is a substituted group selected from the following group: -(C1-C4 alkylene)(phenyl), -(C1-C4 alkylene)(5-6 membered heteroaryl); wherein the substitution refers to substitution by one or more groups selected from the following group: C1-C4 alkyl, fluorine, chlorine, bromine, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyl and nitro.

6. The use according to claim 1, characterized in that Q is a substituted or unsubstituted group selected from the following group: -(C1-C4 alkylene)(phenyl), -(C1-C4 alkylene)(5-6 membered heteroaryl); wherein the substitution refers to substitution by one or more groups selected from the following group: fluorine, chlorine, bromine, C1-C4 haloalkyl, C1-C4 haloalkoxy.

7. The use according to claim 1, characterized in that Q is 8. The use according to claim 1, characterized in that Q is -(C1-C4 alkylene)A, A is 9. The use according to claim 1, characterized in that L is phenyl substituted with fluorine, chlorine, trifluoromethyl or trifluoromethoxy.

10. The use according to claim 1, characterized in that Q is benzyl substituted with fluorine, chlorine or trifluoromethyl.

11. The use according to claim 1, characterized in that L is a phenyl group substituted by fluorine, chlorine, trifluoromethyl or trifluoromethoxy; Q is a benzyl group substituted by fluorine, chlorine or trifluoromethyl.

12. The use according to claim 1, characterized in that The compound is any one of the compounds in Table A, Table A Compounds of formula (I) 13. The use according to claim 1, characterized in that The fungal diseases are selected from: anthracnose, downy mildew, white rust, damping-off, cotton rot, late blight, root rot, damping-off, verticillium wilt, gray mold, brown spot, black spot, leaf spot, early blight, ring rot, leaf blight, stem base rot, rust, smut, sheath blight, powdery mildew, sclerotinia, black spot, and clubroot.

14. A compound having a structure represented by general formula (I) or a pesticide-acceptable salt thereof, In the formula, L is a substituted or unsubstituted phenyl group; wherein the substitution refers to substitution by one or more groups selected from the group consisting of C1-C4 alkyl, halogen, C1-C4 haloalkyl, C3 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl or C1-C4 thioalkyl; M is O - ; Q is -(C1-C4 alkylene)A, in, A is 15. The compound or the pesticide acceptable salt thereof according to claim 14, characterized in that: L is a substituted phenyl group; wherein the substitution refers to substitution by one or more groups selected from the group consisting of C1-C4 alkyl, halogen, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy.

16. The compound according to claim 14 or its pesticide acceptable salt, characterized in that: L is a substituted or unsubstituted phenyl group; wherein the substitution refers to substitution by one or more groups selected from the group consisting of fluorine, chlorine, bromine, C1-C4 haloalkyl or C1-C4 haloalkoxy.

17. The compound according to claim 14 or its pesticidally acceptable salt, characterized in that: L is phenyl, 18. The compound or pesticide-acceptable salt thereof according to claim 14, characterized in that: Q is 19. The compound according to claim 14 or its pesticidally acceptable salt, characterized in that: L is phenyl substituted with fluorine, chlorine, trifluoromethyl or trifluoromethoxy.

20. A compound or a pesticide-acceptable salt thereof, characterized in that: The compound is any one of the compounds in Table A, Table A Compounds of formula (I) 21. A pesticide composition, characterized in that: Include: (a) a compound according to any one of claims 14 to 20 or a pesticidally acceptable salt thereof, or a combination thereof; and (b) pesticide-acceptable carriers and / or excipients.

22. The pesticide composition according to claim 21, characterized in that The pesticide composition also includes: flumorph, chloranil, sulfaquinoxaline, sulfaquinoxaline, thiofluanid, cyfluanid, penthiopyrad, cyclamoxadone, benzylpyridin, cyproconazole, thiocyanamide, cyanamide, dichlorocyanamide, high-efficiency metalaxyl, high-efficiency bensulfuron, carboxin, furpyramide, furamide, flutolanil, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fluoxastrobin, enoxastrobin, fenoxystrobin, pyraclostrobin, trifloxystrobin, trifloxystrobin, high-efficiency imazalil, imazalil, imazalil, prochloraz, oxaquinoxaline, oxaquinoxaline, trifloxystrobin, high-efficiency imazalil, imazalil, cyanamide, imazalil, prochloraz, oxaquinoxaline, mefenamic acid, oxaquinoxaline, flutolanil, pyraclostrobin, pyraclostrobin, oxaquinoxaline ... Cyproconazole, fluquinconazole, difenoconazole, tetrafluconazole, tebuconazole, silfluazole, cyproconazole, high-efficiency diniconazole, diniconazole, flutriafol, hexaconazole, prothioconazole, trichlorfonazole, penconazole, myclobutanil, fenbuconazole, imipenazole, picroconazole, metconazole; thiazoles: ethaconazole, benzathiapiprolin, octhiocyanate, carbendazim, dodecacyclic morpholine, fenpropimorph, tridecanazole; pyrroles: fenpiclonil, fludioxonil, fluazinam, boscalid, flubosacral, pyraclostrobin, cyproconazole, pyrimidine oxime, cyproconazole, chlorfenapyr, flufenac, pyrimidine amine, pyrimidine amine, pyrimidine amine, myclobutanil, myclobutanil, myclobutanil, fluazinam, acaricide Manganese, dicyanoanthraquinone, ethoxyquinoline, 8-hydroxyquinoline, propoxyquinoline, phenoxyquinoline, isoprofenamide, ethotripsy, benzthiopyrad, cymoxanil, thiocarb, dichlorvos, isoprofen, pyraclostrobin, methyl tolclorox, oxazolidinone, blasticidin, kasugamycin, polyoxin, polyoxin, activated ester, indole ester, bronopol, benzylsulfamide, toluenesulfamide, spiroxafil, thiamethoxam, sodium disulfuron, pencuron, tetrachlorophthalide, tricyclazole, allylbenzamide, fenpropidin, chloranil, biguanide, dodine, streptomycin, metalaxyl, bensulfuron, validamycin, Jinggangmycin, pentachloronitrobenzene, Mancozeb, fosetyl-aluminum, ethoxypyrimidine sulfonate, ethoxypyrimidine, dimethoate, triadimefon, methyl thiophanate, benomyl, captan, captan, sulfamethoxam, folpet, furamide, fluchlorinated sclerotin, vinyl sclerotin, 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.

23. The use of the pesticide composition according to claim 21 or 22, characterized in that: Used for preventing and controlling plant fungal diseases or preparing fungicides, wherein the fungicide prevents and controls the following diseases: anthracnose, downy mildew, white rust, damping-off, cotton rot, late blight, root rot, damping-off, verticillium wilt, gray mold, brown spot, black spot, leaf spot, early blight, ring rot, leaf blight, stem base rot, rust, smut, sheath blight, powdery mildew, sclerotinia, black spot, and clubroot.

24. The use according to claim 23, characterized in that The fungal diseases are selected from: anthracnose, downy mildew, white rust, damping-off, cotton rot, late blight, root rot, damping-off, verticillium wilt, gray mold, brown spot, black spot, leaf spot, early blight, ring rot, leaf blight, stem base rot, rust, smut, sheath blight, powdery mildew, sclerotinia, black spot, and clubroot.

25. A method for preventing and controlling plant fungal diseases, characterized in that: The method comprises the step of applying the compound according to any one of claims 14 to 20 or its pesticidally acceptable salt or the pesticidal composition according to claim 21 or 22 to the plant.

26. The method of claim 25, wherein: The fungal diseases are selected from: anthracnose, downy mildew, white rust, damping-off, cotton rot, late blight, root rot, damping-off, verticillium wilt, black spot, gray mold, brown spot, black spot, leaf spot, early blight, ring rot, leaf blight, stem base rot, rust, smut, sheath blight, powdery mildew, sclerotinia, and clubroot.

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