An imidic acid compound and its use as a pesticide

Abstract

The application provides an interdiamide compound as shown in formula (I), wherein Q is a substituted or unsubstituted phenyl, a heterocyclic group or the like; R1 is a substituted or unsubstituted C2-C8 epoxy alkyl, a C3-C9 cycloalkyl or the like; R2 is a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl or the like; X1 and X2 are independently selected from a hydrogen atom, a fluorine atom or the like; Y1 and Y3 are independently a hydrogen atom, a halogen atom or the like; Y2 is a C2-C6 haloalkyl; and W is an oxygen atom or a sulfur atom. The interdiamide compound has no cross resistance with existing insecticides, has the advantages of fast efficacy, low dosage, low toxicity and environmental friendliness on plant pests, and has excellent control effect on resistant Chilo suppressalis, Plutella xylostella, aphids and the like. The application also provides a salt, a composition and an application of the interdiamide compound as a pesticide.

Description

Technical Field

[0001] This invention relates to the field of organic compound technology, specifically to a meta-diamide compound and its application as a pesticide. Background Technology

[0002] In the production of agriculture, forestry, ornamental plants, and nursery crops, pests cause significant economic losses, and pesticides are widely used in agricultural production and planting. However, with the large-scale and prolonged use of pesticides, pests have developed resistance to many existing pesticides, requiring increased dosages to achieve the same effect, causing problems for agricultural production, the environment, and the ecosystem. For example, chlorantraniliprole is a highly effective pesticide for controlling the rice stem borer in rice cultivation; however, after years of continuous use, serious resistance problems have emerged in most parts of the world, posing a significant threat to global rice production. Therefore, there is a need for continuous research and development of new pesticides with high activity, rapid efficacy, low toxicity, and environmental friendliness. Summary of the Invention

[0003] In view of this, this application provides a meta-diamid compound and its application as a pesticide. The meta-diamid compound does not exhibit cross-resistance with existing insecticides. This compound has the advantages of rapid efficacy, low dosage, low toxicity, and environmental friendliness against plant pests. In particular, it has excellent control efficacy against resistant rice stem borers, diamondback moths, and aphids.

[0004] The first aspect of this application provides a m-diamide compound as shown in formula (I):

[0005]

[0006] In formula (Ⅰ), Q is any one of substituted or unsubstituted phenyl groups or substituted or unsubstituted heterocyclic groups;

[0007] R1 is any one of the following: substituted or unsubstituted C3-C9 cycloalkyl, substituted or unsubstituted C2-C8 epoxyalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted olefinic carbonyl, substituted or unsubstituted alkynylic carbonyl, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted C1-C6 alkyl, hydrogen atom, cyano, amino, hydroxyl, and mercapto; wherein, when R1 is a substituted C1-C6 alkyl, the substituent group is selected from cyano, nitro, hydroxyl, carboxyl, thio, and sulfonyl. The group consisting of one or more of the following: alkyl, sulfinyl, carbamoyl, aminosulfonyl, aminosulfinyl, substituted or unsubstituted phenyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted alkoxycarbonyl, substituted or unsubstituted alkenoxycarbonyl, substituted or unsubstituted alkynoxycarbonyl, C1-C6 substituted or unsubstituted alkyl, C3-C6 substituted or unsubstituted cycloalkyl, C1-C6 substituted or unsubstituted alkoxy, C2-C6 substituted or unsubstituted alkenyl, C2-C6 substituted or unsubstituted alkynyl, and substituted or unsubstituted -Si(C1-C6 alkyl)3.

[0008] Alternatively, it may be a group represented as -L1-M-L2, wherein L1 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted heterocyclic, substituted or unsubstituted imino, substituted or unsubstituted alkoxycarbonyl, substituted or unsubstituted alkenoxycarbonyl, substituted or unsubstituted alkynoxycarbonyl, substituted or unsubstituted C1-C6 alkylene, substituted or unsubstituted C3-C9 cycloalkylene, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C2-C8 cyclooxyalkylene, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkyne, substituted or unsubstituted... The substituted C2-C6 enyloxy group, substituted or unsubstituted C2-C6 alkynoxy group, is selected from any one of oxygen atom, sulfur atom, carbonyl group, sulfone group, sulfoxide group, and imino group; L2 is selected from any one of hydrogen atom, substituted or unsubstituted phenyl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkoxycarbonyl group, substituted or unsubstituted alkenoxycarbonyl group, substituted or unsubstituted alkynoxycarbonyl group, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted C3-C9 cycloalkyl group, substituted or unsubstituted C1-C6 alkoxy group, substituted or unsubstituted C2-C6 alkenyl group, and substituted or unsubstituted C2-C6 alkynyl group.

[0009] R2 is selected from any one of hydrogen atom, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C1-C6 alkylcarbonyl, substituted or unsubstituted C2-C6 alkenylcarbonyl, substituted or unsubstituted C2-C6 alkynylcarbonyl, and substituted or unsubstituted C3-C6 cycloalkylcarbonyl.

[0010] X1 and X2 are each independently selected from any one of hydrogen atom, fluorine atom, cyano group or nitro group, and X1 and X2 are not both hydrogen atoms at the same time;

[0011] Y1 and Y3 are each independently one of hydrogen atom, halogen atom, cyano, nitro, substituted or unsubstituted alkyl group of C1-C6, and substituted or unsubstituted alkoxy group of C1-C6;

[0012] Y2 is a C2-C6 haloalkyl group;

[0013] W represents an oxygen atom or a sulfur atom.

[0014] In the embodiments of this application, when R1 is a substituted C2-C8 epoxy alkyl, a substituted C3-C9 cycloalkyl, a substituted phenyl, a substituted heterocyclic group, a substituted olefinic carbonyl, a substituted alkynyl carbonyl, a substituted C1-C6 alkylthio, a substituted C2-C6 alkenyl, or a substituted C2-C6 alkynyl, the substituent group is selected from hydrogen atoms, halogen atoms, cyano, nitro, hydroxyl, carboxyl, mercapto, sulfonyl, sulfinyl, carbamoyl, aminosulfonyl, aminosulfinyl, substituted or unsubstituted benzene. One or more of the following: alkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxycarbonyl group, substituted or unsubstituted alkenoxycarbonyl group, substituted or unsubstituted alkynoxycarbonyl group, C1-C6 substituted or unsubstituted alkyl group, C3-C6 substituted or unsubstituted cycloalkyl group, C1-C6 substituted or unsubstituted alkoxy group, C2-C6 substituted or unsubstituted alkenyl group, C2-C6 substituted or unsubstituted alkynyl group, and substituted or unsubstituted -Si(C1-C6 alkyl)3 group;

[0015] When L1 or L2 is a substituted group, the substituted group is independently selected from one or more of the following: hydrogen atom, halogen atom, cyano, nitro, hydroxyl, carboxyl, mercapto, sulfonyl, sulfinyl, carbamoyl, aminosulfonyl, aminosulfinyl, substituted or unsubstituted phenyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted alkoxycarbonyl, substituted or unsubstituted alkenoxycarbonyl, substituted or unsubstituted alkynoxycarbonyl, C1-C6 substituted or unsubstituted alkyl, C3-C6 substituted or unsubstituted cycloalkyl, C1-C6 substituted or unsubstituted alkoxy, C1-C6 substituted or unsubstituted alkylthio, C2-C6 substituted or unsubstituted alkenyl, C2-C6 substituted or unsubstituted alkynyl, and substituted or unsubstituted -Si(C1-C6 alkyl)3.

[0016] When R2 is a substituted C1-C6 alkyl, substituted C2-C6 alkenyl, substituted C2-C6 alkynyl, substituted C3-C6 cycloalkyl, substituted C1-C6 alkylcarbonyl, substituted C2-C6 alkenylcarbonyl, substituted C2-C6 alkynylcarbonyl, or substituted C3-C6 cycloalkylcarbonyl, the substituent group is selected from one or more of the following: halogen atom, cyano group, substituted or unsubstituted alkoxy group of C1-C6, and substituted or unsubstituted cycloalkyl group of C3-C6.

[0017] In some embodiments of this application, Q is any one of substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted thiophenyl, or substituted or unsubstituted pyrazinyl.

[0018] In the embodiments of this application, when Q is any one of substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted thiophene, or substituted or unsubstituted pyrazinyl, the substituent group in the substituted phenyl, substituted pyridyl, substituted pyrimidinyl, substituted thiophene, or substituted pyrazinyl is selected from one or more of halogen, cyano, nitro, trifluoromethyl, methoxy, and trifluoromethoxy.

[0019] In this application embodiment, R1 is a substituted or unsubstituted C2-C8 epoxy alkyl, a substituted or unsubstituted C3-C9 cycloalkyl, a substituted or unsubstituted C1-C3 alkyl-C3-C5 cycloalkyl, a substituted or unsubstituted C3-C5 cycloalkyl-C1-C3 alkyl, a cyano-substituted C1-C6 alkyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted C1-C6 alkylthio, a substituted or unsubstituted C2-C6 alkenyl, or a substituted or unsubstituted [other compound]. The substituted groups in the substituted C2-C6 alkynyl, hydrogen atom, cyano, amino, hydroxyl, and mercapto groups are any one of C2-C8 epoxy alkyl, substituted C3-C9 cycloalkyl, substituted C3-C5 cycloalkyl, C1-C3 alkyl, substituted furanyl, substituted C1-C6 alkylthio, substituted C2-C6 alkenyl, and substituted C2-C6 alkynyl groups are one or more of C1-C3 alkyl, hydrogen atom, halogen atom, cyano, or furanyl groups.

[0020] Alternatively, it may be a group represented as -L1-M-L2, wherein L1 is selected from any one of substituted or unsubstituted C1-C3 alkylene, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C1-C3 alkoxy, substituted or unsubstituted C1-C3 alkylene amino, and substituted or unsubstituted C1-C3 alkoxycarbonyl, wherein the substituted C1-C3 alkylene, substituted C2-C6 alkenyl, substituted C1-C3 alkoxy, substituted C1-C3 alkylene amino, and substituted C1-C3 alkoxycarbonyl are... The substituent group is one or more of hydrogen atom, halogen atom, cyano or C1-C3 alkoxy; M is selected from oxygen atom, sulfur atom or imino; L2 is selected from hydrogen atom, substituted or unsubstituted C1-C3 alkyl, substituted or unsubstituted C2-C5 alkenyl, substituted or unsubstituted C1-C3 alkoxy, wherein the substituent group of the substituted C1-C3 alkyl, substituted C2-C5 alkenyl or substituted C1-C3 alkoxy is one or more of hydrogen atom, halogen atom, cyano, C1-C3 alkoxy or C1-C3 alkylthio.

[0021] In the embodiments of this application, R1 is any one of the following: substituted or unsubstituted C3-C5 cycloalkyl, substituted or unsubstituted C1-C3 alkyl-C3-C5 cycloalkyl, substituted or unsubstituted C1-C3 alkyl-C3-C5 cycloalkyl-C1-C3 alkyl, cyano-substituted C1-C6 alkyl, substituted or unsubstituted furanyl, substituted or unsubstituted C1-C3 alkathiol, substituted or unsubstituted C2-C5 alkenyl, substituted or unsubstituted C2-C6 alkynyl, hydrogen atom, and cyano group. The substituted groups in the substituted C3-C5 cycloalkyl, substituted C1-C3 alkyl C3-C5 cycloalkyl, substituted C1-C3 alkyl C3-C5 cycloalkyl C1-C3 alkyl, substituted C1-C3 alkoxy, substituted C1-C3 alkylthio C1-C3 alkylamino, substituted furanyl, substituted C1-C3 alkoxycarbonyl, substituted C1-C3 alkyl, and substituted C2-C5 alkenyl are one or more of halogen, cyano, nitro, or furanyl.

[0022] Alternatively, it may be a group represented as -L1-M-L2, wherein L1 is selected from any one of substituted or unsubstituted C1-C3 alkylene, substituted or unsubstituted C2-C6 alkenyl, and substituted or unsubstituted C1-C3 alkoxy, wherein the substituent in the substituted C1-C3 alkylene, substituted C2-C6 alkenyl, and substituted C1-C3 alkoxy is one or more of a halogen atom, a cyano group, or a C1-C3 alkoxy group; M is selected from an oxygen atom; L2 is selected from a hydrogen atom, substituted or unsubstituted C1-C3 alkyl, and substituted or unsubstituted C2-C5 alkenyl, wherein the substituent in the substituted C1-C3 alkyl and substituted C2-C5 alkenyl is one or more of a hydrogen atom, a halogen atom, a cyano group, a C1-C3 alkylthio group, or a C1-C3 alkoxy group;

[0023] R2 is a hydrogen atom, C1-C3 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl or C1-C3 alkylC1-C3 alkoxy, C1-C3 alkyl carbonyl, C2-C5 alkenyl carbonyl, C2-C5 alkynyl carbonyl, or C3-C5 cycloalkyl carbonyl.

[0024] In this embodiment of the application, X1 and X2 are independently selected from hydrogen atoms or fluorine atoms, and X1 and X2 are not both hydrogen atoms; Y1 and Y3 are independently selected from halogen atoms, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy; Y2 is a C2-C6 fluoroalkyl; and W is an oxygen atom.

[0025] In this embodiment of the application, X1 is a fluorine atom, and X2 is a hydrogen atom; Y1 and Y3 are independently a bromine atom, an iodine atom, a methyl atom, a methoxy atom, an ethoxy atom, a trifluoromethyl atom, a pentafluoroethyl atom, a trifluoromethoxy atom, and a pentafluoroethoxy atom, respectively; Y2 is a pentafluoroethyl atom, a heptafluoroisopropyl atom, or a nonafluoro-2-butyl atom; and W is an oxygen atom.

[0026] The second aspect of this application provides a tautomer, enantiomer, diastereomer, or pesticide-acceptable salt thereof of the m-diamide compound provided in the first aspect.

[0027] The third aspect of this application provides the use of the m-diamide compound provided in the first aspect or the m-diamide compound provided in the second aspect, tautomers, enantiomers, diastereomers or pesticide-acceptable salts thereof, in the preparation of an insecticide in the agricultural, forestry or health fields.

[0028] The fourth aspect of this application also provides an insecticide formulation, the insecticide comprising an active ingredient and excipients; the active ingredient comprising tautomers, enantiomers, diastereomers or pesticide-acceptable salts thereof of the m-diamid compounds provided in the first aspect and / or the m-diamid compounds provided in the second aspect.

[0029] In this embodiment of the application, the mass percentage of the active component in the insecticide formulation is 0.1%-99%.

[0030] The fifth aspect of this application also provides an insecticide composition comprising an active ingredient and other active compounds; the active ingredient comprising tautomers, enantiomers, diastereomers or pesticide-acceptable salts thereof of the m-diamid compounds provided in the first aspect and / or the m-diamid compounds provided in the second aspect; the other active compounds comprising one or more of insecticides, baits, disinfectants, acaricides, nematicides, fungicides, growth regulators and herbicides.

[0031] In this embodiment of the application, the mass percentage of the active component in the insecticide composition is 1%-99%. Detailed Implementation

[0032] The technical solutions in the embodiments of this application are described clearly and completely below. Obviously, the described embodiments are only a part of the embodiments of this application, and not all of the embodiments. Based on the embodiments in this application, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of this application.

[0033] This application provides a meta-diamide compound as shown in formula (I):

[0034]

[0035] In formula (Ⅰ), Q is any one of substituted or unsubstituted phenyl groups or substituted or unsubstituted heterocyclic groups;

[0036] R1 is any one of the following: substituted or unsubstituted C3-C9 cycloalkyl, substituted or unsubstituted C2-C8 epoxyalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted olefinic carbonyl, substituted or unsubstituted alkynylic carbonyl, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted C1-C6 alkyl, hydrogen atom, cyano, amino, hydroxyl, and mercapto; wherein, when R1 is a substituted C1-C6 alkyl, the substituent group is selected from cyano, nitro, hydroxyl, carboxyl, thio, and sulfonyl. The group consisting of one or more of the following: alkyl, sulfinyl, carbamoyl, aminosulfonyl, aminosulfinyl, substituted or unsubstituted phenyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted alkoxycarbonyl, substituted or unsubstituted alkenoxycarbonyl, substituted or unsubstituted alkynoxycarbonyl, C1-C6 substituted or unsubstituted alkyl, C3-C6 substituted or unsubstituted cycloalkyl, C1-C6 substituted or unsubstituted alkoxy, C2-C6 substituted or unsubstituted alkenyl, C2-C6 substituted or unsubstituted alkynyl, and substituted or unsubstituted -Si(C1-C6 alkyl)3.

[0037] Alternatively, it may be a group represented as -L1-M-L2, wherein L1 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted heterocyclic, substituted or unsubstituted imino, substituted or unsubstituted alkoxycarbonyl, substituted or unsubstituted alkenoxycarbonyl, substituted or unsubstituted alkynoxycarbonyl, substituted or unsubstituted C1-C6 alkylene, substituted or unsubstituted C3-C9 cycloalkylene, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C2-C8 cyclooxyalkylene, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkyne, substituted or unsubstituted... The substituted C2-C6 enyloxy group, substituted or unsubstituted C2-C6 alkynoxy group, is selected from any one of oxygen atom, sulfur atom, carbonyl group, sulfone group, sulfoxide group, and imino group; L2 is selected from any one of hydrogen atom, substituted or unsubstituted phenyl group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted alkoxycarbonyl group, substituted or unsubstituted alkenoxycarbonyl group, substituted or unsubstituted alkynoxycarbonyl group, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted C3-C9 cycloalkyl group, substituted or unsubstituted C1-C6 alkoxy group, substituted or unsubstituted C2-C6 alkenyl group, and substituted or unsubstituted C2-C6 alkynyl group.

[0038] R2 is selected from any one of hydrogen atom, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C1-C6 alkylcarbonyl, substituted or unsubstituted C2-C6 alkenylcarbonyl, substituted or unsubstituted C2-C6 alkynylcarbonyl, and substituted or unsubstituted C3-C6 cycloalkylcarbonyl.

[0039] X1 and X2 are each independently selected from any one of hydrogen atom, fluorine atom, cyano group or nitro group, and X1 and X2 are not both hydrogen atoms at the same time;

[0040] Y1 and Y3 are each independently one of hydrogen atom, halogen atom, cyano, nitro, substituted or unsubstituted alkyl group of C1-C6, and substituted or unsubstituted alkoxy group of C1-C6;

[0041] Y2 is a C2-C6 haloalkyl group;

[0042] W represents an oxygen atom or a sulfur atom.

[0043] In this application embodiment, when Q is a substituted phenyl or a substituted heterocyclic group, the substituent group is selected from one or more of halogen atoms, cyano, nitro, trifluoromethyl, methoxy, and trifluoromethoxy. In this application embodiment, when the substituent group is selected from a halogen atom, the halogen atom can be, for example, one or more of fluorine, chlorine, and bromine atoms. When there are two or more substituent groups, the substituent groups can be the same or different. In this application embodiment, the above-mentioned substituent groups may further have substituents where possible.

[0044] In some specific embodiments of this application, when Q is a substituted heterocyclic group, Q may be, for example, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiophene group, or a substituted or unsubstituted pyrazinyl group.

[0045] In some specific embodiments of this application, Q can be, for example, phenyl, fluorophenyl, cyanophenyl, trifluoromethylphenyl, difluorophenyl, trifluorophenyl, pyridyl, chloropyridyl, fluoropyridyl, dichlorofluorophenyl, thiophenyl, pyrimidinyl, or pyrazinyl.

[0046] In the embodiments of this application, when R1 is a substituted C1-C6 alkyl group, the substituent group is selected from one or more of the following: cyano, nitro, hydroxyl, carboxyl, thio, sulfonyl, sulfinyl, carbamoyl, aminosulfonyl, aminosulfinyl, substituted or unsubstituted phenyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted alkoxycarbonyl, substituted or unsubstituted alkenyloxycarbonyl, substituted or unsubstituted alkynyl, C1-C6 substituted or unsubstituted cycloalkyl, C3-C6 substituted or unsubstituted alkoxy, C2-C6 substituted or unsubstituted alkenyl, C2-C6 substituted or unsubstituted alkynyl, and substituted or unsubstituted -Si(C1-C6 alkyl)3. In the embodiments of this application, C1-C6 alkyl refers to C1-C6 chain alkyl, including C1-C6 straight-chain alkyl and C1-C6 branched alkyl. In some embodiments of this application, the number of carbon atoms in the C1-C6 alkyl group can be, for example, 1, 2, 3, 4, 5, or 6.

[0047] In the embodiments of this application, when R1 is a substituted C2-C8 epoxy alkyl, a substituted C3-C9 cycloalkyl, a substituted phenyl, a substituted heterocyclic group, a substituted olefinic carbonyl, a substituted alkynyl carbonyl, a substituted C1-C6 alkylthio, a substituted C2-C6 alkenyl, or a substituted C2-C6 alkynyl, the substituent group is selected from hydrogen atoms, halogen atoms, cyano, nitro, hydroxyl, carboxyl, mercapto, sulfonyl, sulfinyl, carbamoyl, aminosulfonyl, aminosulfinyl, substituted or unsubstituted phenyl. One or more of the following: substituted or unsubstituted heterocyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkoxycarbonyl group, substituted or unsubstituted alkenoxycarbonyl group, substituted or unsubstituted alkynoxycarbonyl group, C1-C6 substituted or unsubstituted alkyl group, C3-C6 substituted or unsubstituted cycloalkyl group, C1-C6 substituted or unsubstituted alkoxy group, C2-C6 substituted or unsubstituted alkenyl group, C2-C6 substituted or unsubstituted alkynyl group, and substituted or unsubstituted -Si(C1-C6 alkyl)3 group;

[0048] When L1 or L2 is a substituted group, the substituted group is independently selected from one or more of the following: hydrogen atom, halogen atom, cyano, nitro, hydroxyl, carboxyl, mercapto, sulfonyl, sulfinyl, carbamoyl, aminosulfonyl, aminosulfinyl, substituted or unsubstituted phenyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted alkoxycarbonyl, substituted or unsubstituted alkenoxycarbonyl, substituted or unsubstituted alkynoxycarbonyl, C1-C6 substituted or unsubstituted alkyl, C3-C6 substituted or unsubstituted cycloalkyl, C1-C6 substituted or unsubstituted alkoxy, C1-C6 substituted or unsubstituted alkylthio, C2-C6 substituted or unsubstituted alkenyl, C2-C6 substituted or unsubstituted alkynyl, and substituted or unsubstituted -Si(C1-C6 alkyl)3.

[0049] In the embodiments of this application, when R2 is a substituted C1-C6 alkyl, a substituted C2-C6 alkenyl, a substituted C2-C6 alkynyl, a substituted C3-C6 cycloalkyl, a substituted C1-C6 alkylcarbonyl, a substituted C2-C6 alkenylcarbonyl, a substituted C2-C6 alkynylcarbonyl, or a substituted C3-C6 cycloalkylcarbonyl, the substituent group is selected from one or more of halogen atoms, cyano groups, substituted or unsubstituted alkoxy groups of C1-C6, and substituted or unsubstituted cycloalkyl groups of C3-C6.

[0050] In this application, when there are two or more substituents, the substituents may be the same or different. In this application, the substituents may further have substituents where possible.

[0051] In the embodiments of this application, the number of carbon atoms in C2-C8 epoxy alkyl groups can be, for example, 2, 3, 4, 5, 6, 7, or 8; the number of carbon atoms in C3-C9 cycloalkyl groups can be, for example, 3, 4, 5, 6, 7, 8, or 9; the number of carbon atoms in C1-C6 alkylthio groups can be, for example, 1, 2, 3, 4, 5, or 6; the number of carbon atoms in C2-C6 alkenyl groups can be, for example, 2, 3, 4, 5, or 6; and the number of carbon atoms in C2-C6 alkynyl groups can be, for example, 2, 3, 4, 5, or 6. In the embodiments of this application, the number of carbon atoms in the substituted or unsubstituted alkyl groups of C1-C6 can be, for example, 1, 2, 3, 4, 5, or 6; the number of carbon atoms in the substituted or unsubstituted cycloalkyl groups of C3-C6 can be, for example, 3, 4, 5, or 6; the number of carbon atoms in the substituted or unsubstituted alkoxy groups of C1-C6 can be, for example, 1, 2, 3, 4, 5, or 6; the number of carbon atoms in the substituted or unsubstituted alkenyl groups of C2-C6 can be, for example, 2, 3, 4, 5, or 6; and the number of carbon atoms in the substituted or unsubstituted alkylthio groups of C1-C6 can be, for example, 1, 2, 3, 4, 5, or 6.

[0052] In some embodiments of this application, R1 is a substituted or unsubstituted C2-C8 epoxy alkyl, a substituted or unsubstituted C3-C9 cycloalkyl, a substituted or unsubstituted C1-C3 alkyl-C3-C5 cycloalkyl, a substituted or unsubstituted C3-C5 cycloalkyl-C1-C3 alkyl, a cyano-substituted C1-C6 alkyl, a substituted or unsubstituted furanyl, a substituted or unsubstituted C1-C6 alkylthioyl, a substituted or unsubstituted C2-C6 alkenyl, or a substituted or unsubstituted compound. The substituted groups in the substituted C2-C6 alkynyl, hydrogen atom, cyano, amino, hydroxyl, and mercapto groups are any one of C2-C8 epoxy alkyl, substituted C3-C9 cycloalkyl, substituted C3-C5 cycloalkyl, C1-C3 alkyl, substituted furanyl, substituted C1-C6 alkylthio, substituted C2-C6 alkenyl, and substituted C2-C6 alkynyl groups are one or more of C1-C3 alkyl, hydrogen atom, halogen atom, cyano, or furanyl groups.

[0053] Alternatively, it may be a group represented as -L1-M-L2, wherein L1 is selected from any one of substituted or unsubstituted C1-C3 alkylene, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C1-C3 alkoxy, substituted or unsubstituted C1-C3 alkylene amino, and substituted or unsubstituted C1-C3 alkoxycarbonyl, wherein the substituted C1-C3 alkylene, substituted C2-C6 alkenyl, substituted C1-C3 alkoxy, substituted C1-C3 alkylene amino, and substituted C1-C3 alkoxycarbonyl are... The substituent group is one or more of hydrogen atom, halogen atom, cyano or C1-C3 alkoxy; M is selected from oxygen atom, sulfur atom or imino; L2 is selected from hydrogen atom, substituted or unsubstituted C1-C3 alkyl, substituted or unsubstituted C2-C5 alkenyl, substituted or unsubstituted C1-C3 alkoxy, wherein the substituent group of the substituted C1-C3 alkyl, substituted C2-C5 alkenyl or substituted C1-C3 alkoxy is one or more of hydrogen atom, halogen atom, cyano, C1-C3 alkoxy or C1-C3 alkylthio.

[0054] In some specific embodiments of this application, R1 is any one of the following: substituted or unsubstituted C3-C5 cycloalkyl, substituted or unsubstituted C1-C3 alkyl-C3-C5 cycloalkyl, substituted or unsubstituted C1-C3 alkyl-C3-C5 cycloalkyl-C1-C3 alkyl, cyano-substituted C1-C6 alkyl, substituted or unsubstituted furanyl, substituted or unsubstituted C1-C3 alkylthio, substituted or unsubstituted C2-C5 alkenyl, substituted or unsubstituted C2-C6 alkynyl, hydrogen atom, and cyano group. The substituted group in the substituted C3-C5 cycloalkyl, substituted C1-C3 alkyl C3-C5 cycloalkyl, substituted C1-C3 alkyl C3-C5 cycloalkyl C1-C3 alkyl, substituted C1-C3 alkoxy, substituted C1-C3 alkylthio C1-C3 alkylamino, substituted furanyl, substituted C1-C3 alkoxycarbonyl, substituted C1-C3 alkyl, and substituted C2-C5 alkenyl is one or more of halogen, cyano, nitro, or furanyl.

[0055] Alternatively, it may be a group represented as -L1-M-L2, wherein L1 is selected from any one of substituted or unsubstituted C1-C3 alkylene, substituted or unsubstituted C2-C6 alkenyl, and substituted or unsubstituted C1-C3 alkoxy, wherein the substituent in the substituted C1-C3 alkylene, substituted C2-C6 alkenyl, and substituted C1-C3 alkoxy is one or more of a halogen atom, a cyano group, or a C1-C3 alkoxy group; M is selected from an oxygen atom; L2 is selected from a hydrogen atom, substituted or unsubstituted C1-C3 alkyl, and substituted or unsubstituted C2-C5 alkenyl, wherein the substituent in the substituted C1-C3 alkyl and substituted C2-C5 alkenyl is one or more of a hydrogen atom, a halogen atom, a cyano group, a C1-C3 alkylthio group, or a C1-C3 alkoxy group.

[0056] In some specific embodiments of this application, R1 may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, ethylcyclopropyl, -ethyl(2-methylcyclopropyl), -methyl(3-methylcyclobutyl), -methyl(3-methylcyclopentyl), -CH2SCH3, -CH2SCH2CH3, -CH2SCH3, -furan-2-yl, -methyl(furan-2-yl), -CH2CN, -C2H4CN, -CH=CH2, -CH2CH=CH2CH3, -C(CH3)=CH2, -C≡CH, -C≡CCH3, -CH2C≡CCH3, -CH2OCH3, -CH2OCH2CH3, -CH2CH2OCH3, -CH2OCH2OCH2Cl, or -CH2OCH2CH2OCH3.

[0057] In some embodiments of this application, R1 may be, for example, a substituted or unsubstituted C3-C5 cycloalkyl, a substituted or unsubstituted C1-C3 alkyl-C3-C5 cycloalkyl, a substituted or unsubstituted C1-C3 alkyl-C3-C5 cycloalkyl-C1-C3 alkyl, a substituted or unsubstituted C1-C3 alkoxy, a substituted or unsubstituted C1-C3 alkylthio, a substituted or unsubstituted C1-C3 alkylamino, or a substituted or unsubstituted C1-C3 alkoxycarbonyl. When R1 contains a cyclic structure such as a cycloalkyl group or a heteroatom such as O, N, or S, the meta-diamide compound exhibits superior pest control efficacy. In some specific embodiments of this application, R1 may be, for example, cyclopropyl, methylcyclopropyl, isopropoxy, -CH2OCH3, or -CH2OCH2CH3.

[0058] In the embodiments of this application, the number of carbon atoms in C1-C6 alkyl carbonyl groups can be, for example, 1, 2, 3, 4, 5, or 6; the number of carbon atoms in C2-C6 alkenyl carbonyl groups can be, for example, 2, 3, 4, 5, or 6; the number of carbon atoms in C2-C6 alkynyl carbonyl groups can be, for example, 2, 3, 4, 5, or 6; and the number of carbon atoms in C3-C6 cycloalkyl carbonyl groups can be, for example, 3, 4, 5, or 6.

[0059] In some embodiments of this application, R2 can be a hydrogen atom, a C1-C3 alkyl group, a C2-C5 alkenyl group, a C2-C5 alkynyl group, a C3-C5 cycloalkyl group, a C1-C3 alkylC1-C3 alkoxy group, a C1-C3 alkyl carbonyl group, a C2-C5 alkenyl carbonyl group, a C2-C5 alkynyl carbonyl group, or a C3-C5 cycloalkyl carbonyl group. In some specific embodiments of this application, R2 can be, for example, a hydrogen atom, a methyl group, -CH=CH2, -CH2CH=CH2, -CH2OCH3, -CH3CN, -CH2C≡CH, a cyclopropyl group, -C(O)cyclopropyl, or -C(O)CH=CH2.

[0060] In some embodiments of this application, X1 is a fluorine atom; X2 is a hydrogen atom; Y1 and Y3 are independently a bromine atom, an iodine atom, a methyl atom, a methoxy atom, an ethoxy atom, a trifluoromethyl atom, a pentafluoroethyl atom, a trifluoromethoxy atom, and a pentafluoroethoxy atom, respectively; Y2 is a pentafluoroethyl atom, a heptafluoroisopropyl atom, or a nonafluoro-2-butyl atom; and W is an oxygen atom.

[0061] This application enhances the lipophilicity of the m-diamid compound by selecting suitable groups for R1 and R2, and by the synergistic effect of suitable groups between R1 and R2. This makes it easier for pests to absorb the compound when applied in the insecticidal field, resulting in better insecticidal activity. Currently, commercially available m-diamid compounds produce their efficacy through demethylation in organisms, but pests develop resistance after long-term use. The m-diamid compound provided in this application produces its efficacy through deacylation in organisms. This type of m-diamid compound has not yet been used in the insecticidal field, and its application is less prone to resistance development. Furthermore, this application employs a special design to the structure of the m-diamid compound and the grafting positions of R1 and R2, such that the R1 group is attached to the C in C=W, and the C in C=W is grafted onto the N in the m-diamid compound that is attached to the carbonyl group. This reduces polarity, making it less likely for water molecules to form hydrogen bonds, thus reducing hydrophilicity and increasing lipophilicity. This results in the m-diamid compound exhibiting better lipophilicity, which can further enhance its insecticidal efficacy. This is because the modified structure has a faster enzyme metabolism rate in vivo, making it easier to produce efficacy more quickly through deacylation reactions in vivo.

[0062] The m-diamide compounds provided in this application do not exhibit cross-resistance with existing insecticides. Compared with existing insecticides on the market, these compounds have advantages such as rapid efficacy, low dosage, low toxicity, and environmental friendliness against plant pests. They are particularly effective against resistant rice stem borers, diamondback moths, and aphids.

[0063] This application provides a tautomer, enantiomer, diastereomer, or pesticide-acceptable salt thereof of the aforementioned meta-diamide compound.

[0064] This application also provides the use of the aforementioned m-diamide compounds or tautomers, enantiomers, diastereomers or pesticide-acceptable salts thereof in the agricultural, forestry or health fields for the preparation of insecticides.

[0065] In this application, the insecticide is used to control pests including, but not limited to, beetles (coleoptera), such as bean weevil, corn weevil, red flour beetle, potato ladybug, slender click beetle, multicolored scarab beetle, potato leaf beetle, leaf beetle, pine longhorn beetle, rice root weevil, brown powder beetle; and lepidopteran pests, such as gypsy moth, yellow tent caterpillar, cabbage white butterfly Japanese subspecies, beet armyworm, cabbage looper, rice stem borer, corn borer, dried fruit leaf roller, apple leafroller, yellow cutworm, large wax moth, diamondback moth, tobacco bud moth, and citrus leafminer. Hemiptera pests, such as black-tailed leafhoppers, brown planthoppers, Comstock mealybugs, arrowhead scale insects, peach aphids, apple aphids, cotton aphids, turnip aphids, pear lace bugs, *Toona sinensis*, and greenhouse whiteflies; Thysanoptera pests, such as palm thrips and western flower thrips; Orthoptera pests, such as African mole crickets and African migratory locusts; Blattodea pests, such as German cockroaches, American cockroaches, yellow-breasted subterranean termites, and domestic termites; Diptera pests, such as houseflies, Aedes aegypti, gray ground fly, Culex pipiens pallens, Anopheles sinensis, Culex tritaeniorhynchus, and clover leafminer, among one or more of these. In some embodiments of this application, the insecticide may also refer to the acaricide, and the pests used for control include, but are not limited to, spiders (Arachnida), such as ticks (Acari order), for example, ticks of the families Soft ticks, Hard ticks, and Sarcoptidae, such as the long-spotted tick, tropical flower tick, Persian sharp tick, cattle tick, small cattle tick, castor hard tick, chicken skin mites, sheep scabies, and human scabies; mites of the genus *Scutellaria*, such as apple rust mite; mites of the genus *Ceratophyllum*, such as *Polyphagus lateralis*; mites of the genus *Scutellaria*, such as *Scutellaria purpurata*; mites of the genus *Tetranychus*, such as *Tetranychus cinnabarinus*, *Tetranychus scabra*, *Tetranychus pacificans*, cotton spider mite, and two-spotted spider mite; and one or more of the following: apple spider mite and citrus spider mite.

[0066] This application also provides an insecticide formulation comprising an active ingredient, which includes the aforementioned m-diamid compounds and / or tautomers, enantiomers, diastereomers, or pesticide-acceptable salts thereof; the insecticide formulation further includes one or more excipients.

[0067] In this application, the insecticide formulations include, but are not limited to, solutions, emulsions, wettable powders, granular wettable powders, suspensions, powders, foams, pastes, tablets, granules, aerosols, natural reagents impregnated with active compounds, synthetic reagents impregnated with active compounds, microcapsules, seed coating agents, formulations equipped with combustion devices (the combustion devices may be chimneys and fog cans, canisters and coils, etc.), as well as cold fog agents, hot fog agents, etc. These insecticide formulations or animal parasite control agents can be prepared by known methods, for example, by mixing the active component with fillers (such as liquid diluents or carriers, liquefied gas diluents or carriers, solid diluents or carriers), and optionally with surfactants (i.e., emulsifiers and / or dispersants and / or foaming agents).

[0068] In this application, the mass percentage of the active ingredient in the insecticide formulation is 0.1%-99%. In some embodiments of this application, the mass percentage of the active ingredient in the insecticide formulation may be, for example, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 99%. In some specific embodiments of this application, the mass percentage of the active ingredient in the insecticide formulation may be 0.5%-90%.

[0069] This application also provides an insecticide composition comprising an active ingredient and other active compounds; the active ingredient comprises the m-diamid compounds provided above in this application and / or tautomers, enantiomers, diastereomers or pesticide-acceptable salts thereof of the m-diamid compounds provided above in this application; the other active compounds comprise one or more of insecticides, poison baits, disinfectants, acaricides, nematicides, fungicides, growth regulators and herbicides.

[0070] In some embodiments of this application, the mass percentage of the active ingredient in the insecticide composition is 1%-99%. In some specific embodiments of this application, the mass percentage of the active ingredient in the insecticide composition can be, for example, 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 99%. In some embodiments of this application, the mass percentage of the active ingredient in the insecticide composition is 20%-70%.

[0071] The insecticide, insecticide formulation, and insecticide composition provided in this application do not exhibit cross-resistance with existing insecticides. Compared with existing insecticides on the market, this compound has advantages such as rapid efficacy, low dosage, low toxicity, and environmental friendliness against plant pests. It is particularly effective against rice resistant rice stem borer, diamondback moth, and aphids.

[0072] The embodiments of the present invention will be further described below with reference to several examples.

[0073] Specifically, the meta-diamid compounds described in this application are as shown in formula (II), and some of the meta-diamid compounds are shown in Table 1, but the meta-diamid compounds described in this invention are not limited to all the compounds in Table 1.

[0074]

[0075] Table 1: Meta-diamide compounds with the chemical structure shown in formula (II):

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] Example 1

[0104] Preparation methods of compound number 146 in Table 1: (1) Synthesis of tert-butyl 2-fluoro-3-nitrobenzoate

[0105]

[0106] At room temperature, di-tert-butyl dicarbonate (18.62 mL, 81.03 mmol), triethylamine (14.98 mL, 108.04 mmol), and 4-dimethylaminopyridine (1.98 g, 16.21 mmol) were added to a solution of 2-fluoro-3-nitrobenzoic acid (10 g, 54.02 mmol) in dichloromethane (100 mL). The reaction mixture was then stirred at room temperature for 18 h. After TLC detection, the reaction mixture was quenched in water (100 mL), allowed to stand, and separated. The aqueous phase was extracted with dichloromethane (50 mL), and the organic phases were combined. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to obtain the crude product. The crude product was purified by rapid column chromatography (petroleum ether:ethyl acetate = 99:1) to obtain a pale yellow oil (8.34 g, yield 64.00%).

[0107] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 8.35-8.31 (m, 1H), 8.18-8.13 (m, 1H), 7.54-7.50 (m, 1H), 1.55 (s, 9H).

[0108] (2) Synthesis of tert-butyl 2-fluoro-3-aminobenzoate

[0109]

[0110] Under nitrogen protection, 10% palladium on carbon (2.4 g) was added to a 200 mL solution of tert-butyl ester (8.34 g, 34.57 mmol) in ethyl acetate. The mixture was then purged three times with hydrogen, and stirred for 18 h under hydrogen (15 Psi) atmosphere. The reaction was stopped by TLC. The reaction solution was filtered through a diatomaceous earth layer, and the filter cake was washed with ethyl acetate (50 mL). The filtrate was concentrated to obtain the crude product. The crude product was purified by rapid column chromatography (petroleum ether:ethyl acetate = 90:10) to obtain a pale yellow oil (6.10 g, yield 83.52%).

[0111] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 6.94-6.85 (m, 3H), 5.32 (s, 2H), 1.52 (s, 9H).

[0112] (3) Synthesis of tert-butyl 3-benzoamide-2-fluorobenzoate

[0113]

[0114] At room temperature, tert-butyl 3-amino-2-fluorobenzoate (2.10 g, 9.94 mmol) and triethylamine (4.13 mL, 29.82 mmol) were added to a solution of dichloromethane (25 mL), followed by the slow dropwise addition of a solution of benzoyl chloride (1.27 mL, 10.94 mmol). After the addition was complete, the reaction mixture was stirred at room temperature for 2 h. The reaction was monitored by LCMS until completion. The reaction mixture was then poured into water (30 mL), extracted three times with ethyl acetate (60 mL), and the organic phases were combined. The organic phase was washed once with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to obtain the crude product. The crude product was slurried with petroleum ether (50 mL), filtered, and the filter cake was washed with petroleum ether (30 mL) and dried under vacuum to obtain a white solid (2.40 g, yield 76.56%).

[0115] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 10.23 (s, 1H), 8.01–7.98 (m, 2H), 7.84–7.80 (m, 1H), 7.69–7.60 (m, 2H), 7.56–7.52 (m, 2H), 7.31 (t, J = 7.9Hz, 1H), 1.55 (s, 9H).

[0116] (4) Synthesis of tert-butyl 3-(N-acryloylbenzamido)-2-fluorobenzoate

[0117]

[0118] Under ice bath conditions, tert-butyl 3-benzoamide-2-fluorobenzoate (2.00 g, 7.32 mmol) was added to a tetrahydrofuran (50 mL) solution, followed by slow, partial addition of sodium hydride (0.63 g, 15.85 mmol) until the entire solution was added. The mixture was purged with nitrogen three times, and the reaction was continued for 20 minutes. Then, a tetrahydrofuran (5 mL) solution of acryloyl chloride (1.29 mL, 15.85 mmol) was slowly added dropwise to the above reaction system. After the addition was complete, the reaction mixture was stirred under ice bath conditions for 1 hour. The reaction was monitored by LCMS until complete. The reaction solution was quenched in an ammonium chloride aqueous solution (20 mL), extracted three times with ethyl acetate (50 mL), and the organic phases were combined. The organic phase was washed once with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 0-20%) to give a white solid (0.70 g, yield 29.88%).

[0119] The 1H NMR spectrum (600MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 7.84-7.80 (m, 1H), 7.73-7.69 (m, 1H), 7.67-7.65 (m, 2H), 7.57-7.53 (m, 1H), 7.47-7.43 (m, 2H), 7.33 (t, J = 7.9Hz, 1H), 6.56-6.49 (m, 1H), 6.34-6.29 (m, 1H), 5.89-5.86 (m, 1H), 1.52 (s, 9H).

[0120] (5) Synthesis of 3-(N-acryloylbenzamido)-2-fluorobenzoic acid

[0121]

[0122] At room temperature, tert-butyl 3-(N-acryloylbenzamido)-2-fluorobenzoate (1.30 g, 3.52 mmol) was added to a solution of dichloromethane (20 mL), followed by slow dropwise addition of a solution of trifluoroacetic acid (7 mL, 91.48 mmol). After the addition was complete, the mixture was stirred at room temperature for 2 h. The reaction was monitored by LCMS until completion, and the reaction solution was concentrated to obtain the crude product. The crude product was purified by preparative high-performance liquid chromatography (Puningtech-Pntulips-C18-10 μm-30*250 mm (A: 0.1% FA / H2O, B: ACN = 80-20%)) to obtain a pale yellow solid (0.60 g, yield 54.06%).

[0123] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 13.49 (s, 1H), 7.88-7.84 (m, 1H), 7.72-7.68 (m, 1H), 7.66-7.64 (m, 2H), 7.57-7.52 (m, 1H), 7.46-7.42 (m, 2H), 7.33 (t, J = 7.9Hz, 1H), 6.58-6.52 (m, 1H), 6.32 (dd, J = 1.5, 16.9Hz, 1H), 5.90-5.87 (m, 1H).

[0124] (6) Synthesis of 3-(N-acryloylbenzamido)-2-fluoro-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide

[0125]

[0126] 3-(N-Acryloylbenzamido)-2-fluorobenzoic acid (0.40 g, 1.28 mmol) was dissolved in ultra-dry dichloromethane. Oxaloyl chloride (0.32 g, 2.56 mmol) was added under ice bath conditions, followed by 1-2 drops of N,N-dimethylformamide. The reaction was carried out at room temperature for 2-3 h, and then concentrated under reduced pressure to obtain 3-(N-Acryloylbenzamido)-2-fluorobenzoyl chloride. 3-(N-Acryloylbenzamido)-2-fluorobenzoyl chloride was dissolved in acetonitrile. The temperature was raised to 50-60 °C, and 4-(perfluoropropane-2-yl)-2-(trifluoromethyl)aniline (0.42 g, 1.28 mmol) was added. The reaction was maintained at this temperature until completion. After concentration under reduced pressure, the solution was purified by silica gel column chromatography to give a white solid (0.46 g, yield 57.50%).

[0127] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 10.53 (s, 1H), 8.11 (d, J = 8.6Hz, 1H), 8.02-7.97 (m, 1H), 7.94 (s, 1H), 7.79-7.67 (m, 4H), 7.58-7.52 (m, 1H), 7.50-7.38 (m, 3H), 6.56 (dd, J = 16.9, 10.3Hz, 1H), 6.35 (dd, J = 16.9, 1.5Hz, 1H), 5.90 (dd, J = 10.3, 1.5Hz, 1H).

[0128] Example 2

[0129] Preparation methods of compound number 147 in Table 1:

[0130]

[0131] 3-(N-acryloylbenzamido)-2-fluoro-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide (0.40 g, 0.64 mmol) was dissolved in acetonitrile, and sodium hydroxide (0.04 g, 0.96 mmol) was added. The mixture was stirred in an ice bath for 10 min, and N-bromosuccinimide (0.23 g, 1.28 mmol) was added. The reaction was allowed to proceed for 2.5 h–3.5 h. After the reaction was complete, the sodium hydroxide was filtered off, the mixture was evaporated to dryness, and dichloromethane was added. The mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, saturated sodium sulfite solution (1:1 ratio), and saturated sodium chloride solution. After drying with anhydrous sodium sulfate, the mixture was evaporated to dryness to give a white solid (0.26 g, yield 57.78%).

[0132] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.84 (s, 1H), 8.44 (s, 1H), 7.96 (s, 1H), 7.76–7.67 (m, 4H), 7.58 (t, J = 7.4 Hz, 1H), 7.46 (dd, J = 12.5, 5.0 Hz, 3H), 6.55 (dd, J = 16.9, 10.3 Hz, 1H), 6.34 (dd, J = 16.9, 1.5 Hz, 1H), 5.90 (dd, J = 10.3, 1.5 Hz, 1H).

[0133] Example 3

[0134] Preparation methods of compound number 155 in Table 1: (1) Synthesis of methyl 3-benzamido-2-fluorobenzoate

[0135]

[0136] Methyl 3-amino-2-fluorobenzoate (3.00 g, 17.74 mmol) was added to a reaction flask and dissolved in dichloromethane. Pyridine (3.16 g, 39.92 mmol) was added, followed by dropwise addition of benzoyl chloride (2.49 g, 17.74 mmol) under ice bath conditions. After the reaction was complete, the mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated sodium chloride solution. The solution was dried over anhydrous sodium sulfate and then evaporated to dryness to give a pink solid (4.35 g, yield 89.69%).

[0137] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.25 (s, 1H), 8.03–7.96 (m, 2H), 7.92–7.84 (m, 1H), 7.75 (ddd, J = 8.1, 6.6, 1.7 Hz, 1H), 7.63 (ddd, J = 6.5, 3.8, 1.2 Hz, 1H), 7.55 (dd, J = 10.2, 4.6 Hz, 2H), 7.36 (t, J = 7.9 Hz, 1H), 3.88 (s, 3H).

[0138] ESI-MS (m / z): [MH-] Theoretical value: 272.0728, Measured value: 272.0731.

[0139] (2) Synthesis of 3-benzamido-2-fluorobenzoic acid

[0140]

[0141] Method 1: Methyl 3-benzamido-2-fluorobenzoate (3.00 g, 10.98 mmol) was added to a mixture of 5% potassium hydroxide solution and methanol in a 1:1 volume ratio, and hydrolyzed at 25℃-35℃ for 3-4 h. After the reaction was completed, dilute hydrochloric acid was added for acidification, and a solid precipitated out. The solid was filtered, washed several times with distilled water, and dried to obtain a light pink solid (2.42 g, yield 84.91%).

[0142]

[0143] Method 2: 3-Amino-2-fluorobenzoic acid (3.00 g, 19.34 mmol) was dissolved in saturated sodium carbonate solution, and benzoyl chloride (2.99 g, 21.27 mmol) was dissolved in ethyl acetate and added to the solution. The reaction was allowed to proceed overnight. The inorganic phase was then acidified with dilute hydrochloric acid, and a solid precipitated out. The solid was filtered, washed several times with distilled water, and dried to obtain a light pink solid (2.50 g, yield 49.90%).

[0144] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 13.32 (s, 1H), 10.21 (s, 1H), 7.99 (dd, J = 5.2, 3.3 Hz, 2H), 7.87–7.77 (m, 1H), 7.75–7.70 (m, 1H), 7.65–7.59 (m, 1H), 7.58–7.50 (m, 2H), 7.32 (t, J = 7.9 Hz, 1H).

[0145] ESI-MS (m / z): [MH-] Theoretical value: 258.0572, Measured value: 258.0569.

[0146] (3) Synthesis of 3-benzamido-2-fluorobenzoate benzyl ester

[0147]

[0148] 3-Benzamido-2-fluorobenzoic acid (3.00 g, 11.57 mmol) and thionyl chloride (10 mL) were added to a reaction flask and stirred under reflux for 3-4 h. The mixture was then concentrated under reduced pressure to obtain 3-benzamido-2-fluorobenzoyl chloride. 3-Benzamido-2-fluorobenzoyl chloride and pyridine (1.37 g, 17.36 mmol) were added to a solution of benzyl alcohol (1.88 g, 17.36 mmol) in acetonitrile (20 mL), and the reaction was allowed to proceed overnight. The mixture was washed successively with saturated sodium carbonate solution, dilute hydrochloric acid (2 mol / L), and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then evaporated to dryness to give a pale purple solid (3.60 g, yield 89.11%).

[0149] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.26 (s, 1H), 8.00 (d, J = 7.3 Hz, 2H), 7.89 (t, J = 6.9 Hz, 1H), 7.78 (t, J = 6.6 Hz, 1H), 7.67-7.31 (m, 9H), 5.39 (s, 2H).

[0150] ESI-MS (m / z): [M+Na] + Theoretical value: 372.1012, measured value: 372.1004.

[0151] (4) Synthesis of 3-(N-(cyclopropanecarbonyl)benzamido)-2-fluorobenzoate benzyl ester

[0152]

[0153] Benzyl 3-benzamido-2-fluorobenzoate (3.00 g, 8.59 mmol) was dissolved in dichloromethane, and 4-dimethylaminopyridine (0.10 g, 0.86 mmol) and triethylamine (1.74 g, 17.18 mmol) were added. After stirring for a while, cyclopropylformyl chloride (1.35 g, 12.89 mmol) was added, and the reaction was carried out at 35-39 °C. The reaction was monitored by TLC until completion. After the reaction was completed, the product was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then evaporated to dryness to obtain a pink, oily, viscous liquid (3.02 g, yield 84.12%).

[0154] The 1H NMR spectrum (600MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 7.94 (t, J = 6.7Hz, 1H), 7.82 (t, J = 6.9Hz, 1H), 7.68 (d, J = 7.4Hz, 2H), 7.56 (t, J = 7.4Hz, 1H), 7.50-7.35 (m, 8H), 5.37 (s, 2H), 1.95-1.87 (m, 1H), 0.93 (ddd, J = 10.8, 7.2, 3.1Hz, 4H).

[0155] ESI-MS (m / z): [M+Na] + Theoretical value: 440.1274, measured value: 440.1264.

[0156] (5) Synthesis of 3-(N-(cyclopropanecarbonyl)benzamido)-2-fluorobenzoic acid

[0157]

[0158] 3-(N-(cyclopropanecarbonyl)benzamido)-2-fluorobenzoate benzyl ester (3.00 g, 7.19 mmol) was dissolved in ethyl acetate, and 0.60 g of 5% palladium on carbon (55% water) was added. Hydrogen gas was bubbled through the solution, and the reaction was allowed to proceed for 24 h. After the reaction was complete, the palladium on carbon was filtered off, and the solution was evaporated to dryness to give a white solid (1.13 g, yield 48.09%).

[0159] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 13.46 (s, 1H), 7.92-7.85 (m, 1H), 7.77-7.71 (m, 1H), 7.70-7.65 (m, 2H), 7.59-7.52 (m, 1H), 7.46 (t, J = 7.5Hz, 2H), 7.34 (dd, J = 13.7, 5.8Hz, 1H), 1.96-1.84 (m, 1H), 1.01-0.87 (m, 4H).

[0160] ESI-MS (m / z): [MH-] Theoretical value: 326.0834, Measured value: 326.0832.

[0161] (6) Synthesis of 3-(N-(cyclopropanecarbonyl)benzamido)-2-fluoro-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide

[0162]

[0163] 3-(N-(cyclopropanecarbonyl)benzamido)-2-fluorobenzoic acid (1.00 g, 3.06 mmol) was dissolved in ultra-dry dichloromethane. Oxaloyl chloride (0.78 g, 6.12 mmol) was added under ice bath conditions, followed by 1-2 drops of N,N-dimethylformamide. The reaction was carried out at room temperature for 2-3 h, and then concentrated under reduced pressure to obtain 3-(N-(cyclopropanecarbonyl)benzamido)-2-fluorobenzoyl chloride. 3-(N-(cyclopropanecarbonyl)benzamido)-2-fluorobenzoyl chloride was dissolved in acetonitrile. The temperature was raised to 50-60 °C, and 4-(perfluoropropane-2-yl)-2-(trifluoromethyl)aniline (1.01 g, 3.06 mmol) was added. The reaction was maintained at this temperature until completion. After concentration under reduced pressure, the solution was purified by silica gel column chromatography to give a white solid (1.06 g, yield 54.36%).

[0164] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.52 (s, 1H), 8.12 (d, J = 8.6Hz, 1H), 7.99 (d, J = 8.6Hz, 1H), 7.94 (s, 1H), 7.75 (ddd, J = 20.0, 11.8, 4.7Hz, 4H), 7.58 (t, J = 7.4Hz, 1H), 7.47 (dt, J = 21.1, 7.8Hz, 3H), 1.93–1.86 (m, 1H), 1.01–0.89 (m, 4H).

[0165] ESI-MS (m / z): [MH-] Theoretical value: 637.0991, Measured value: 637.1001.

[0166] Example 4

[0167] Preparation methods of compound number 156 in Table 1:

[0168]

[0169] 3-(N-(cyclopropanecarbonyl)benzamido)-2-fluoro-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide (1.00 g, 1.57 mmol) was dissolved in acetonitrile, and sodium hydroxide (0.09 g, 2.36 mmol) was added. The mixture was stirred in an ice bath for 10 min, and N-bromosuccinimide (0.56 g, 3.14 mmol) was added. The reaction was allowed to proceed for 2.5-3.5 h. After the reaction was complete, the sodium hydroxide was filtered off, the mixture was evaporated to dryness, and dichloromethane was added. The mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, saturated sodium sulfite solution (1:1 ratio), and saturated sodium chloride solution. After drying with anhydrous sodium sulfate, the mixture was evaporated to dryness to give a white solid (0.63 g, yield 55.75%).

[0170] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 10.83 (s, 1H), 8.43 (s, 1H), 7.97 (s, 1H), 7.75 (ddd, J = 17.5, 8.7, 1.4Hz, 4H), 7.61-7.56 (m, 1H), 7.48 (dt, J = 12.5, 7.8Hz, 3H), 1.92-1.84 (m, 1H), 0.95 (ddt, J = 20.5, 7.7, 3.9Hz, 4H).

[0171] ESI-MS (m / z): [MH-] Theoretical value: 715.0096, measured value: 715.0109.

[0172] Example 5

[0173] Preparation methods of compound number 170 in Table 1: (1) Synthesis of benzyl benzoate 2-fluoro-3-(N-(2-methoxyacetyl)benzamido)benzoate

[0174]

[0175] Benzyl 3-benzamido-2-fluorobenzoate (3.00 g, 8.59 mmol) was dissolved in ultra-dry tetrahydrofuran. Sodium hydride (0.41 g, 17.18 mmol) was added in portions under ice bath conditions. After stirring for 30 min, methoxyacetyl chloride (2.80 g, 25.77 mmol) was added, and the mixture was allowed to react at room temperature for 2.5-3.5 h. After the reaction was complete, the mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated sodium chloride solution. After drying with anhydrous sodium sulfate, the product was evaporated to dryness and purified by silica gel column chromatography to obtain a pink, oily, viscous liquid (2.54 g, yield 70.17%).

[0176] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 7.87 (dd, J = 10.5, 4.0 Hz, 1H), 7.74 (t, J = 6.6 Hz, 1H), 7.58–7.54 (m, 2H), 7.50–7.34 (m, 8H), 7.32 (t, J = 7.9 Hz, 1H), 5.35 (s, 2H), 4.50 (s, 2H), 3.32 (s, 3H).

[0177] ESI-MS (m / z): [M+Na] + Theoretical value: 444.1223, measured value: 444.1211.

[0178] (2) Synthesis of 2-fluoro-3-(N-(2-methoxyacetyl)benzamido)benzoic acid

[0179]

[0180] Benzyl benzoate (3.00 g, 7.12 mmol) was dissolved in ethyl acetate, and 0.60 g of 5% palladium on carbon (55% water) was added. Hydrogen gas was bubbled through the solution, and the reaction was allowed to proceed for 24 h. After the reaction was complete, the palladium on carbon was filtered off, and the solution was evaporated to dryness to give a white solid (1.25 g, yield 52.97%).

[0181] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 13.16 (s, 1H), 7.82 (t, J = 6.7Hz, 1H), 7.67 (t, J = 6.9Hz, 1H), 7.57 (d, J = 6.1Hz, 2H), 7.48 (t, J = 7.4Hz, 1H), 7.39 (t, J = 7.6Hz, 2H), 7.27 (t, J = 7.9Hz, 1H), 4.50 (s, 2H), 3.33 (s, 3H).

[0182] ESI-MS (m / z): [MH-] Theoretical value: 330.0783, Measured value: 330.0788.

[0183] (3) Synthesis of 2-fluoro-3-(N-(2-methoxyacetyl)benzamido)-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide

[0184]

[0185] 2-Fluoro-3-(N-(2-methoxyacetyl)benzamido)benzoic acid (1.00 g, 3.02 mmol) was dissolved in ultra-dry dichloromethane. Oxaloyl chloride (0.77 g, 6.04 mmol) was added under ice bath conditions, followed by 1-2 drops of N,N-dimethylformamide. The reaction was carried out at room temperature for 2-3 hours, and then concentrated under reduced pressure to obtain 2-fluoro-3-(N-(2-methoxyacetyl)benzamido)benzoyl chloride. 2-Fluoro-3-(N-(2-methoxyacetyl)benzamido)benzoyl chloride was dissolved in acetonitrile. The temperature was raised to 50-60 °C, and 4-(perfluoropropane-2-yl)-2-(trifluoromethyl)aniline (0.99 g, 3.02 mmol) was added. The reaction was maintained at this temperature until completion. After concentration under reduced pressure, the solution was purified by silica gel column chromatography to give a white solid (1.08 g, yield 55.67%).

[0186] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.47 (s, 1H), 8.12 (d, J = 8.4Hz, 1H), 7.99 (d, J = 8.6Hz, 1H), 7.94 (s, 1H), 7.70 (dd, J = 13.2, 6.7Hz, 2H), 7.63 (d, J = 7.3Hz, 2H), 7.52 (t, J = 7.4Hz, 1H), 7.45-7.35 (m, 3H), 4.49 (s, 2H), 3.33 (s, 3H).

[0187] ESI-MS (m / z): [MH-] Theoretical value: 641.0940, Measured value: 641.0948.

[0188] Example 6

[0189] Preparation methods of compound number 171 in Table 1:

[0190]

[0191] 2-Fluoro-3-(N-(2-methoxyacetyl)benzamido)-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide (1.00 g, 1.56 mmol) was dissolved in acetonitrile, and sodium hydroxide (0.09 g, 2.34 mmol) was added. The mixture was stirred in an ice bath for 10 min, and N-bromosuccinimide (0.56 g, 3.12 mmol) was added. The reaction was allowed to proceed for 2.5 h–3.5 h. After the reaction was complete, the sodium hydroxide was filtered off, the mixture was evaporated to dryness, and dichloromethane was added. The mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, saturated sodium sulfite solution (1:1 ratio), and saturated sodium chloride solution. After drying with anhydrous sodium sulfate, the mixture was evaporated to dryness to give a white solid (0.71 g, yield 62.83%).

[0192] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 10.78 (s, 1H), 8.43 (s, 1H), 7.98 (s, 1H), 7.74–7.66 (m, 2H), 7.62 (d, J = 7.3 Hz, 2H), 7.52 (t, J = 7.4 Hz, 1H), 7.40 (dt, J = 13.5, 7.8 Hz, 3H), 4.49 (s, 2H), 3.33 (s, 3H).

[0193] ESI-MS (m / z): [MH-] Theoretical value: 719.0045, Measured value: 719.0054.

[0194] Example 7

[0195] Preparation methods of compound number 491 in Table 1: (1) Synthesis of methyl 2-fluoro-3-(4-fluorobenzoamide)benzoate

[0196]

[0197] Methyl 3-amino-2-fluorobenzoate (3.00 g, 17.74 mmol) was added to a reaction flask and dissolved in dichloromethane. Pyridine (3.16 g, 39.92 mmol) was added, followed by dropwise addition of p-fluorobenzoyl chloride (2.81 g, 17.74 mmol) under ice bath conditions. After the reaction was complete, the mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated sodium chloride solution. After drying with anhydrous sodium sulfate, the product was evaporated to dryness to give a pink solid (4.65 g, yield 89.94%).

[0198] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.28 (s, 1H), 8.12-8.02 (m, 2H), 7.90-7.82 (m, 1H), 7.81-7.69 (m, 1H), 7.46-7.28 (m, 3H), 3.88 (s, 3H).

[0199] ESI-MS (m / z): [MH-] Theoretical value: 290.0634, Measured value: 290.0636.

[0200] (2) Synthesis of 2-fluoro-3-(4-fluorobenzoamido)benzoic acid

[0201]

[0202] Method 1: Methyl 2-fluoro-3-(4-fluorobenzoamide)benzoate (3.00 g, 10.30 mmol) was added to a 1:1 volume ratio of 5% potassium hydroxide to methanol and hydrolyzed at 25-35°C for 3-4 hours. After the reaction was complete, dilute hydrochloric acid was added for acidification, and a solid precipitated out. The solid was filtered, washed several times with distilled water, and dried to obtain a light pink solid (2.66 g, yield 93.01%).

[0203] Method 2: 3-Amino-2-fluorobenzoic acid (3.00 g, 19.34 mmol) was dissolved in saturated sodium carbonate solution, and p-fluorobenzoyl chloride (3.37 g, 21.27 mmol) was dissolved in ethyl acetate and added to the solution. The reaction was carried out overnight. The inorganic phase was acidified with dilute hydrochloric acid, and a solid precipitated out. The solid was filtered, washed several times with distilled water, and dried to obtain a light pink solid (2.75 g, yield 51.31%).

[0204] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 13.31 (s, 1H), 10.25 (s, 1H), 8.11–8.04 (m, 2H), 7.86–7.79 (m, 1H), 7.77–7.69 (m, 1H), 7.44–7.28 (m, 3H).

[0205] ESI-MS (m / z): [MH-] Theoretical value: 276.0478, Measured value: 276.0481.

[0206] (3) Synthesis of 2-fluoro-3-(4-fluorobenzoamido)benzoate benzyl ester

[0207]

[0208] 2-fluoro-3-(4-fluorobenzoamide)benzoic acid (3.00 g, 10.82 mmol) and thionyl chloride (10 mL) were added to a reaction flask and stirred under reflux for 3-4 h. The mixture was then concentrated under reduced pressure to obtain 2-fluoro-3-(4-fluorobenzoamide)benzoyl chloride. 2-fluoro-3-(4-fluorobenzoamide)benzoyl chloride and pyridine (1.28 g, 16.23 mmol) were added to a solution of benzyl alcohol (1.76 g, 16.23 mmol) in acetonitrile (20 mL), and the reaction was allowed to proceed overnight. The mixture was washed successively with saturated sodium carbonate solution, dilute hydrochloric acid (2 mol / L), and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then evaporated to dryness to give a light pink solid (3.52 g, yield 88.66%).

[0209] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 10.30 (s, 1H), 8.12-8.04 (m, 2H), 7.89 (t, J = 7.4Hz, 1H), 7.79 (dd, J = 10.3, 3.9Hz, 1H), 7.53-7.46 (m, 2H), 7.45-7.31 (m, 6H), 5.39 (s, 2H).

[0210] ESI-MS (m / z): [MH-] Theoretical value: 366.0947, Measured value: 366.0946.

[0211] (4) Synthesis of 3-(N-(cyclopropanecarbonyl)-4-fluorobenzoamide)-2-fluorobenzoate benzyl ester

[0212]

[0213] Benzyl 2-fluoro-3-(4-fluorobenzoamide)benzoate (3.00 g, 8.17 mmol) was dissolved in dichloromethane, and 4-dimethylaminopyridine (0.10 g, 0.82 mmol) and triethylamine (1.65 g, 16.34 mmol) were added. After stirring for a while, cyclopropylformyl chloride (1.28 g, 12.26 mmol) was added, and the reaction was carried out at 35-39 °C. The reaction was monitored by TLC until completion. After the reaction was completed, the product was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then evaporated to dryness to obtain a pink, oily, viscous liquid (3.14 g, yield 88.20%).

[0214] The 1H NMR spectrum (600MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 8.01-7.92 (m, 1H), 7.88-7.81 (m, 1H), 7.80-7.72 (m, 2H), 7.50-7.25 (m, 8H), 5.37 (s, 2H), 1.93-1.83 (m, 1H), 1.00-0.87 (m, 4H).

[0215] ESI-MS (m / z): [M+Na] + Theoretical value: 458.1180, measured value: 458.1177.

[0216] (5) Synthesis of 3-(N-(cyclopropanecarbonyl)-4-fluorobenzoamide)-2-fluorobenzoic acid

[0217]

[0218] 3-(N-(cyclopropanecarbonyl)-4-fluorobenzamido)-2-fluorobenzoate benzyl ester (3.00 g, 6.89 mmol) was dissolved in ethyl acetate, and 0.60 g of 5% palladium on carbon (55% water) was added. Hydrogen gas was bubbled through the solution, and the reaction was allowed to proceed for 24 h. After the reaction was complete, the palladium on carbon was filtered off, and the solution was evaporated to dryness to give a white solid (1.21 g, yield 50.84%).

[0219] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 13.41 (s, 1H), 7.89 (dd, J = 10.5, 4.0 Hz, 1H), 7.80–7.73 (m, 3H), 7.34 (dt, J = 17.6, 8.3 Hz, 3H), 1.92–1.85 (m, 1H), 0.99–0.88 (m, 4H).

[0220] ESI-MS (m / z): [MH-] Theoretical value: 344.0740, Measured value: 344.0740.

[0221] (6) Synthesis of 3-(N-(cyclopropanecarbonyl)-4-fluorobenzamido)-2-fluoro-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide

[0222]

[0223] 3-(N-(cyclopropanecarbonyl)-4-fluorobenzamido)-2-fluorobenzoic acid (1.00 g, 2.90 mmol) was dissolved in ultra-dry dichloromethane. Oxaloyl chloride (0.74 g, 5.80 mmol) was added under ice bath conditions, followed by 1-2 drops of N,N-dimethylformamide. The reaction was carried out at room temperature for 2-3 hours, and then concentrated under reduced pressure to obtain 3-(N-(cyclopropanecarbonyl)-4-fluorobenzamido)-2-fluorobenzoyl chloride. 3-(N-(cyclopropanecarbonyl)-4-fluorobenzamido)-2-fluorobenzoyl chloride was dissolved in acetonitrile. The temperature was raised to 50-60 °C, and 4-(perfluoropropane-2-yl)-2-(trifluoromethyl)aniline (0.95 g, 2.90 mmol) was added. The reaction was maintained at this temperature until completion. After concentration under reduced pressure, the sample was purified by silica gel column chromatography to give a white solid (1.01 g, yield 53.16%).

[0224] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.52 (s, 1H), 8.12 (d, J = 8.7Hz, 1H), 8.00 (d, J = 8.6Hz, 1H), 7.94 (s, 1H), 7.84–7.75 (m, 4H), 7.47 (t, J = 7.9Hz, 1H), 7.33 (t, J = 8.8Hz, 2H), 1.91–1.83 (m, 1H), 1.02–0.90 (m, 4H).

[0225] ESI-MS (m / z): [MH-] Theoretical value: 655.0897, Measured value: 655.0904.

[0226] Example 8

[0227] Preparation method of compound number 492 in Table 1:

[0228]

[0229] 3-(N-(cyclopropanecarbonyl)-4-fluorobenzamido)-2-fluoro-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide (1.00 g, 1.52 mmol) was dissolved in acetonitrile, and sodium hydroxide (0.09 g, 2.28 mmol) was added. The mixture was stirred in an ice bath for 10 min, and N-bromosuccinimide (0.54 g, 3.04 mmol) was added. The reaction was allowed to proceed for 2.5 h–3.5 h. After the reaction was complete, the sodium hydroxide was filtered off, the mixture was evaporated to dryness, and dichloromethane was added. The mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, saturated sodium sulfite solution (1:1 ratio), and saturated sodium chloride solution. After drying with anhydrous sodium sulfate, the mixture was evaporated to dryness to give a white solid (0.65 g, yield 58.04%).

[0230] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 10.84 (s, 1H), 8.43 (s, 1H), 7.97 (s, 1H), 7.85-7.70 (m, 4H), 7.53-7.44 (t, 1H), 7.34 (t, J = 8.8Hz, 2H), 1.90-1.82 (m, 1H), 0.95 (ddd, J = 11.2, 7.4, 3.3Hz, 4H).

[0231] ESI-MS (m / z): [MH-] Theoretical value: 733.0002, Measured value: 733.0013.

[0232] Example 9

[0233] Preparation methods of compound number 506 in Table 1: (1) Synthesis of benzyl benzoate 2-fluoro-3-(4-fluoro-N-(2-methoxyacetyl)benzamido)benzoate

[0234]

[0235] Benzyl 2-fluoro-3-(4-fluorobenzoamide)benzoate (3.00 g, 8.17 mmol) was dissolved in ultra-dry tetrahydrofuran. Sodium hydride (0.39 g, 16.34 mmol) was added in portions under ice bath conditions. After stirring for 30 min, methoxyacetyl chloride (2.66 g, 24.51 mmol) was added, and the mixture was allowed to react at room temperature for 2.5-3.5 h. After the reaction was complete, the mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated sodium chloride solution. After drying with anhydrous sodium sulfate, the product was evaporated to dryness and purified by silica gel column chromatography to obtain a pink, oily, viscous liquid (2.57 g, yield 71.59%).

[0236] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 7.93-7.86 (m, 1H), 7.79-7.72 (m, 1H), 7.69-7.62 (m, 2H), 7.48-7.31 (m, 6H), 7.24 (t, J=8.8Hz, 2H), 5.35 (s, 2H), 4.54-4.43 (m, 2H), 3.32 (s, 3H).

[0237] ESI-MS (m / z): [M+Na] + Theoretical value: 462.1129, measured value: 462.1120.

[0238] (2) Synthesis of 2-fluoro-3-(4-fluoro-N-(2-methoxyacetyl)benzamido)benzoic acid

[0239]

[0240] Benzyl benzoate (3.00 g, 6.83 mmol) was dissolved in ethyl acetate, and 0.60 g of 5% palladium on carbon (55% water) was added. Hydrogen gas was bubbled through the solution, and the reaction was allowed to proceed for 24 h. After the reaction was complete, the palladium on carbon was filtered off, and the solution was evaporated to dryness to give a white solid (1.28 g, yield 53.56%).

[0241] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 13.42 (s, 1H), 7.85 (t, J = 6.8 Hz, 1H), 7.72-7.63 (m, 3H), 7.28 (ddd, J = 24.3, 12.7, 5.9 Hz, 3H), 4.48 (s, 2H), 3.33 (s, 3H).

[0242] ESI-MS (m / z): [MH-] Theoretical value: 348.0689, Measured value: 348.0694.

[0243] (3) Synthesis of 2-fluoro-3-(4-fluoro-N-(2-methoxyacetyl)benzamido)-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide

[0244]

[0245] 2-Fluoro-3-(4-fluoro-N-(2-methoxyacetyl)benzamido)benzoic acid (1.00 g, 2.86 mmol) was dissolved in ultra-dry dichloromethane. Oxaloyl chloride (0.73 g, 5.72 mmol) was added under ice bath conditions, followed by 1-2 drops of N,N-dimethylformamide. The reaction was carried out at room temperature for 2-3 hours, and then concentrated under reduced pressure to obtain 2-fluoro-3-(4-fluoro-N-(2-methoxyacetyl)benzamido)benzoyl chloride. 2-Fluoro-3-(4-fluoro-N-(2-methoxyacetyl)benzamido)benzoyl chloride was dissolved in acetonitrile. The temperature was raised to 50-60 °C, and 4-(perfluoropropane-2-yl)-2-(trifluoromethyl)aniline (0.94 g, 2.86 mmol) was added. The reaction was maintained at this temperature until completion. After concentration under reduced pressure, the sample was purified by silica gel column chromatography to give a white solid (1.11 g, yield 58.73%).

[0246] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.48 (s, 1H), 8.12 (d, J = 8.9Hz, 1H), 7.99 (d, J = 8.6Hz, 1H), 7.95 (s, 1H), 7.75-7.67 (m, 4H), 7.40 (t, J = 7.8Hz, 1H), 7.30-7.23 (t, 2H), 4.47 (s, 2H), 3.33 (s, 3H).

[0247] ESI-MS (m / z): [MH-] Theoretical value: 659.0846, Measured value: 659.0853.

[0248] Example 10

[0249] Preparation method of compound number 507 in Table 1:

[0250]

[0251] 2-Fluoro-3-(4-fluoro-N-(2-methoxyacetyl)benzamido)-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide (1.00 g, 1.51 mmol) was dissolved in acetonitrile, and sodium hydroxide (0.09 g, 2.27 mmol) was added. The mixture was stirred in an ice bath for 10 min, and N-bromosuccinimide (0.54 g, 3.02 mmol) was added. The reaction was allowed to proceed for 2.5 h–3.5 h. After the reaction was complete, the sodium hydroxide was filtered off, the mixture was evaporated to dryness, and dichloromethane was added. The mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, saturated sodium sulfite solution (1:1 ratio), and saturated sodium chloride solution. After drying with anhydrous sodium sulfate, the mixture was evaporated to dryness to give a white solid (0.73 g, yield 65.18%).

[0252] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 10.78 (s, 1H), 8.44 (s, 1H), 7.97 (s, 1H), 7.77-7.67 (m, 4H), 7.42 (t, J = 7.6Hz, 1H), 7.27 (t, J = 8.8Hz, 2H), 4.47 (s, 2H), 3.33 (s, 3H).

[0253] ESI-MS (m / z): [MH-] Theoretical value: 736.9951, Measured value: 736.9953.

[0254] Example 11

[0255] Preparation methods of compound number 971 in Table 1: (1) Synthesis of 2-fluoro-N-(2-methyl-4-(perfluoropropane-2-yl)phenyl)-3-nitrobenzamide

[0256]

[0257] 2-Fluoro-3-nitrobenzoic acid (3.00 g, 16.21 mmol) and thionyl chloride (10 mL) were added to a reaction flask and stirred under reflux for 2 h. The mixture was then concentrated under reduced pressure to give 2-fluoro-3-nitrobenzoyl chloride. 2-Fluoro-3-nitrobenzoyl chloride and pyridine (1.76 g, 22.39 mmol) were added to a solution of 4-(perfluoropropane-2-yl)-2-methylaniline (2.94 g, 10.69 mmol) in dichloromethane (20 mL). The reaction was stopped after 5 hours at room temperature. The mixture was washed with dilute hydrochloric acid (2 mol / L), saturated potassium carbonate solution, and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then evaporated to dryness to give a pale yellow solid (4.50 g, yield 95.23%).

[0258] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.36 (s, 1H), 8.33 (t, J = 7.1Hz, 1H), 8.12 (t, J = 6.1Hz, 1H), 7.87 (d, J = 8.4Hz, 1H), 7.63-7.54 (m, 3H), 2.40 (s, 3H).

[0259] ESI-MS (m / z): [MH-] Theoretical value: 441.0490, Measured value: 441.0491.

[0260] (2) Synthesis of 3-amino-2-fluoro-N-(2-methyl-4-(perfluoropropane-2-yl)phenyl)benzamide

[0261]

[0262] N-(2-bromo-6-methyl-4-(perfluoropropane-2-yl)phenyl)-2-fluoro-3-nitrobenzamide (3.00 g, 6.78 mmol) was dissolved in ethanol (20 ml), and stannous chloride dihydrate (6.12 g, 27.12 mmol) was added in portions. The mixture was heated to 60 °C and reacted for 4 h. The reaction solution was evaporated to dryness under reduced pressure, dissolved in ethyl acetate solution, and saturated sodium carbonate solution was added. A solid was formed. The solid was filtered off, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure to give a brown solid (2.02 g, yield 72.14%).

[0263] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 9.91 (s, 1H), 7.84 (d, J = 8.5Hz, 1H), 7.59–7.48 (m, 2H), 6.99 (t, J = 7.7Hz, 1H), 6.92 (td, J = 8.2, 1.7Hz, 1H), 6.86–6.79 (m, 1H), 5.40 (s, 2H), 2.38 (s, 3H).

[0264] (3) Synthesis of 2-chloro-N-(2-fluoro-3-((2-methyl-4-(perfluoropropane-2-yl)phenyl)carbamoyl)phenyl)nicotinamide

[0265]

[0266] 3-Amino-2-fluoro-N-(2-methyl-4-(perfluoropropane-2-yl)phenyl)benzamide (3.00 g, 7.28 mmol) was dissolved in acetonitrile, and 2-chloronicotinyl chloride (1.28 g, 7.28 mmol) was added. The mixture was reacted at 80 °C for 2 h. The crude product was evaporated to dryness and, without further processing, was a pale yellow solid (3.23 g, yield 80.35%).

[0267] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 10.72 (s, 1H), 10.16 (s, 1H), 8.55 (dd, J = 4.8, 1.9Hz, 1H), 8.17-8.05 (m, 2H), 7.86 (d, 1H), 7.57 (dt, J = 13.8, 6.8Hz, 4H), 7.39 (t, J = 7.9Hz, 1H), 2.40 (s, 3H).

[0268] (4) Synthesis of 2-chloro-N-(cyclopropenyl)-N-(2-fluoro-3-((2-methyl-4-(perfluoropropane-2-yl)phenyl)carbamoyl)phenyl)nicotinamide

[0269]

[0270] 2-Chloro-N-(2-fluoro-3-((2-methyl-4-(perfluoropropane-2-yl)phenyl)carbamoyl)phenyl)nicotinamide (1.00 g, 1.81 mmol) was dissolved in dichloromethane, and triethylamine (0.28 g, 2.72 mmol) was added, followed by cyclopropylformyl chloride (0.21 g, 1.99 mmol). The reaction mixture was reacted at room temperature for 4-5 h. The reaction solution was washed with dilute hydrochloric acid (2 mol / L), saturated sodium bicarbonate, and saturated brine, dried over anhydrous sodium sulfate, and then evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography to give a white solid (0.36 g, 32.14%).

[0271] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.26 (s, 1H), 8.50 (dd, J = 4.8, 1.9Hz, 1H), 8.08 (dd, J = 7.6, 1.9Hz, 1H), 7.86 (ddd, J = 17.1, 14.4, 7.4Hz, 3H), 7.55 (dt, J = 13.0, 9.7Hz, 4H), 2.39 (s, 3H), 1.76–1.66 (m, 1H), 0.98–0.88 (m, 4H).

[0272] ESI-MS (m / z): [MH-] Theoretical value: 618.0836, Measured value: 618.0836.

[0273] Example 12

[0274] Preparation methods of compound number 978 in Table 1: (1) Synthesis of 3-(2-chloronicotinamide)-2-fluorobenzoic acid

[0275]

[0276] 3-Amino-2-fluorobenzoic acid (3.00 g, 19.34 mmol) was dissolved in a saturated sodium carbonate solution, and 2-chloronicotinyl chloride (3.74 g, 21.27 mmol) was dissolved in ethyl acetate and added to the solution. The reaction was carried out overnight. The inorganic phase was acidified with dilute hydrochloric acid, and a solid precipitated out. The solid was filtered, washed several times with distilled water, and dried to give a light pink solid (2.65 g, yield 46.49%).

[0277] The 1H NMR spectrum (600MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 13.39 (s, 1H), 10.65 (s, 1H), 8.56 (dd, J = 4.8, 1.8Hz, 1H), 8.16-8.06 (m, 2H), 7.72 (t, J = 6.5Hz, 1H), 7.58 (dt, J = 10.8, 5.4Hz, 1H), 7.35 (t, J = 7.9Hz, 1H).

[0278] ESI-MS (m / z): [MH-] Theoretical value: 293.0135, Measured value: 293.0136.

[0279] (2) Synthesis of 3-(2-chloronicotinamide)-2-fluorobenzoate benzyl ester

[0280]

[0281] 3-(2-chloronicotinamide)-2-fluorobenzoic acid (3.00 g, 10.18 mmol) and thionyl chloride (10 mL) were added to a reaction flask and stirred under reflux for 3-4 h. The mixture was then concentrated under reduced pressure to obtain 3-(2-chloronicotinamide)-2-fluorobenzoyl chloride. 3-(2-chloronicotinamide)-2-fluorobenzoyl chloride and pyridine (1.21 g, 15.27 mmol) were added to a solution of benzyl alcohol (1.65 g, 15.27 mmol) in acetonitrile (20 mL), and the reaction was allowed to proceed overnight. The mixture was washed successively with saturated sodium carbonate solution, dilute hydrochloric acid (2 mol / L), and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then evaporated to dryness to give a pale purple solid (3.58 g, yield 91.33%).

[0282] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 10.68 (s, 1H), 8.54 (dd, J = 4.8, 1.7Hz, 1H), 8.17 (t, J = 6.9Hz, 1H), 8.09 (dd, J = 7.5, 1.7Hz, 1H), 7.76 (t, J = 6.5Hz, 1H), 7.60-7.54 (m, 1H), 7.48 (d, J = 7.3Hz, 2H), 7.39 (dt, J = 15.8, 7.2Hz, 4H), 5.39 (s, 2H).

[0283] ESI-MS (m / z): [MH-] Theoretical value: 383.0604, Measured value: 383.0607.

[0284] (3) Synthesis of benzyl 3-(2-chloro-N-(cyclopropanecarbonyl)nicotinamide)-2-fluorobenzoate

[0285]

[0286] Benzyl 3-(2-chloronicotinamide)-2-fluorobenzoate (3.00 g, 7.80 mmol) was dissolved in dichloromethane, and 4-dimethylaminopyridine (0.10 g, 0.78 mmol) and triethylamine (1.58 g, 15.60 mmol) were added. After stirring for a while, cyclopropylformyl chloride (0.98 g, 9.36 mmol) was added, and the reaction was carried out at 35-39 °C. The reaction was monitored by TLC until completion. After the reaction was completed, the product was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then evaporated to dryness to obtain a pink, oily, viscous liquid (3.12 g, yield 88.39%).

[0287] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 8.49 (dd, J = 4.8, 1.8 Hz, 1H), 8.07 (td, J = 7.9, 1.6 Hz, 2H), 7.97 (dd, J = 10.5, 4.1 Hz, 1H), 7.58–7.47 (m, 4H), 7.42 (t, J = 7.5 Hz, 2H), 7.38 (d, J = 7.2 Hz, 1H), 5.41 (s, 2H), 1.70 (ddd, J = 12.4, 7.6, 4.7 Hz, 1H), 0.96–0.84 (m, 4H).

[0288] ESI-MS (m / z): [M+Na] + Theoretical value: 475.0837, measured value: 475.0827.

[0289] (4) Synthesis of 3-(2-chloro-N-(cyclopropanecarbonyl)nicotinamide)-2-fluorobenzoic acid

[0290]

[0291] Benzyl 3-(2-chloro-N-(cyclopropanecarbonyl)nicotinamide)-2-fluorobenzoate (3.00 g, 6.62 mmol) was dissolved in ethyl acetate, and 0.60 g of 5% palladium on carbon (55% water) was added. Hydrogen gas was bubbled through the solution, and the reaction was allowed to proceed for 24 h. After the reaction was complete, the palladium on carbon was filtered off, and the solution was evaporated to dryness to give a pale yellow solid (1.97 g, yield 82.08%).

[0292] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 13.17 (s, 1H), 8.48 (dd, J = 4.8, 1.8Hz, 1H), 8.06 (dd, J = 7.6, 1.7Hz, 1H), 8.00 (dd, J = 10.5, 4.0Hz, 1H), 7.90 (t, J = 6.6Hz, 1H), 7.54 (dd, J = 7.6, 4.8Hz, 1H), 7.47 (t, J = 7.9Hz, 1H), 1.72–1.64 (m, 1H), 0.94–0.87 (m, 4H).

[0293] ESI-MS (m / z): [MH-] Theoretical value: 361.0397, Measured value: 361.0398.

[0294] (5) Synthesis of 2-chloro-N-(cyclopropanecarbonyl)-N-(2-fluoro-3-((4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)carbamoyl)phenyl)nicotinamide

[0295]

[0296] 3-(2-chloro-N-(cyclopropanecarbonyl)nicotinamide)-2-fluorobenzoic acid (1.00 g, 2.76 mmol) was dissolved in ultra-dry dichloromethane. Oxaloyl chloride (0.70 g, 5.52 mmol) was added under ice bath conditions, followed by 1-2 drops of N,N-dimethylformamide. The reaction was carried out at room temperature for 2-3 hours, and then concentrated under reduced pressure to obtain 3-(2-chloro-N-(cyclopropanecarbonyl)nicotinamide)-2-fluorobenzoyl chloride. 3-(2-chloro-N-(cyclopropanecarbonyl)nicotinamide)-2-fluorobenzoyl chloride was dissolved in acetonitrile. The temperature was raised to 50-60 °C, and 4-(perfluoropropane-2-yl)-2-(trifluoromethyl)aniline (0.91 g, 2.76 mmol) was added. The reaction was maintained at this temperature until completion. After concentration under reduced pressure, the sample was purified by silica gel column chromatography to give a white solid (1.02 g, yield 54.84%).

[0297] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.58 (s, 1H), 8.50 (dd, J = 4.8, 1.8Hz, 1H), 8.14 (d, J = 8.6Hz, 1H), 8.08 (dd, J = 7.6, 1.8Hz, 1H), 8.03 (d, J = 8.6Hz, 1H), 7.95 (s, 1H), 7.92–7.85 (m, 2H), 7.59–7.52 (m, 2H), 1.75–1.67 (m, 1H), 0.97–0.89 (m, 4H).

[0298] ESI-MS (m / z): [MH-] Theoretical value: 672.0554, Measured value: 672.0558.

[0299] Example 13

[0300] Preparation methods of compound number 979 in Table 1:

[0301]

[0302] 2-Chloro-N-(cyclopropanecarbonyl)-N-(2-fluoro-3-((4-(perfluoropropane-2-yl)-2-(trifluoromethyl)yl)carbamoyl)phenyl)nicotinamide (1.00 g, 1.48 mmol) was dissolved in acetonitrile, and sodium hydroxide (0.09 g, 2.22 mmol) was added. The mixture was stirred in an ice bath for 10 min, and N-bromosuccinimide (0.53 g, 2.96 mmol) was added. The reaction was allowed to proceed for 2.5 h–3.5 h. After the reaction was complete, the sodium hydroxide was filtered off, the mixture was evaporated to dryness, and dichloromethane was added. The mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, saturated sodium sulfite solution (1:1 ratio), and saturated sodium chloride solution. After drying with anhydrous sodium sulfate, the mixture was evaporated to dryness to give a pale yellow solid (0.59 g, yield 53.15%).

[0303] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ10.90 (s, 1H), 8.50 (dd, J = 4.8, 1.8Hz, 1H), 8.45 (s, 1H), 8.09 (dt, J = 6.3, 3.2Hz, 1H), 7.98 (s, 1H), 7.91 (dd, J = 10.7, 4.2Hz, 1H), 7.85 (t, J = 6.4Hz, 1H), 7.61-7.51 (m, 2H), 1.71 (d, J = 5.3Hz, 1H), 0.93 (d, J = 7.4Hz, 4H).

[0304] ESI-MS (m / z): [MH-] Theoretical value: 751.9638, Measured value: 751.9639.

[0305] Example 14

[0306] Preparation methods of compound number 1121 in Table 1: (1) Synthesis of 2-fluoro-3-nitro-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide

[0307]

[0308] 2-Fluoro-3-nitrobenzoic acid (1.66 g, 8.97 mmol) and thionyl chloride (10 mL) were added to a reaction flask and stirred under reflux for 2 h. The mixture was then concentrated under reduced pressure to give 2-fluoro-3-nitrobenzoyl chloride. 2-Fluoro-3-nitrobenzoyl chloride was added to a solution of 4-(perfluoropropane-2-yl)-2-(trifluoromethyl)aniline (2.36 g, 7.17 mmol) in acetonitrile (20 mL), and the mixture was heated to 80 °C and reacted for 8 h. The product was washed with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then evaporated to dryness to give a white solid (3.20 g, yield 90.16%).

[0309] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ10.74 (s, 1H), 8.37-8.32 (m, 1H), 8.15-8.03 (m, 3H), 7.94 (s, 1H), 7.61 (t, J = 7.9Hz, 1H).

[0310] ESI-MS (m / z): [MH-] Theoretical value: 495.0208, Measured value: 495.0203.

[0311] (2) Synthesis of N-(2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-nitrobenzamide

[0312]

[0313] 2-fluoro-3-nitro-N-(4-(perfluoropropane-2-yl)-2-(trifluoromethyl)phenyl)benzamide (2.00 g, 4.03 mmol), sodium hydroxide (0.30 g, 7.50 mmol), and acetonitrile (10 mL) were added to a reaction flask. N-bromosuccinimide (0.92 g, 5.17 mmol) was added in portions, and the reaction was stopped after 7 h at room temperature. The reaction solution was evaporated to dryness under reduced pressure, dissolved in ethyl acetate solution, washed with saturated sodium sulfite solution, saturated sodium bicarbonate solution, and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and evaporated to dryness again to give a white solid (1.76 g, yield 76.35%).

[0314] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ11.13 (s, 1H), 8.45 (d, J = 1.1Hz, 1H), 8.41-8.35 (m, 1H), 8.06 (ddd, J = 7.5, 5.9, 1.6Hz, 1H), 7.98 (s, 1H), 7.65 (t, J = 8.0Hz, 1H).

[0315] ESI-MS (m / z): [MH-] Theoretical value: 572.9313, Measured value: 572.9318.

[0316] (3) Synthesis of 3-amino-N-(2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide

[0317]

[0318] N-(2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-nitrobenzamide (1.76 g, 3.07 mmol) was dissolved in ethanol (20 ml), and stannous chloride dihydrate (2.76 g, 12.26 mmol) was added in portions. The mixture was heated to 60 °C and reacted for 4 h. The reaction solution was evaporated to dryness under reduced pressure, dissolved in ethyl acetate solution, washed with 10% sodium hydroxide aqueous solution, and the solid was filtered off. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure to give a yellow solid (1.20 g, yield 71.99%).

[0319] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ10.74(s,1H), 8.37-8.32(m,1H), 8.15-8.03(m,4H), 7.94(s,1H), 7.61(t,J=7.9Hz,1H).

[0320] ESI-MS (m / z): [MH-] Theoretical value: 542.9571, Measured value: 542.9574.

[0321] (4) Synthesis of N-(2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-(4-fluorobenzamido)benzamide

[0322]

[0323] 3-Amino-N-(2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide (1.20 g, 2.21 mmol) was added to 10 mL of acetonitrile, the temperature was raised to 80 °C, and p-fluorobenzoyl chloride (0.34 g, 2.14 mmol) was added dropwise. The reaction mixture was reacted for 2 h. The reaction solution was evaporated to dryness under reduced pressure, dissolved in ethyl acetate solution, washed with saturated sodium carbonate and saturated brine, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The residue was purified by column chromatography (eluent: hexane: ethyl acetate = 10:1) to give a white solid (1.40 g, yield 95.27%).

[0324] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.78 (s, 1H), 10.34 (s, 1H), 8.44 (s, 1H), 8.13–8.07 (m, 2H), 7.98 (s, 1H), 7.84 (t, J = 7.5Hz, 1H), 7.62–7.57 (m, 1H), 7.44–7.36 (m, 3H).

[0325] ESI-MS (m / z): [MH-] Theoretical value: 664.9739, Measured value: 664.9747.

[0326] (5) Synthesis of N-(2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)-N-(cyclopropanecarbonyl)-2-fluoro-3-(4-fluorobenzamido)benzamide

[0327]

[0328] N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluoro-3-(4-fluorobenzamido)benzamide (1.00 g, 1.50 mmol) was dissolved in dichloromethane (10 ml), and triethylamine (0.23 g, 2.31 mmol) was added. The mixture was stirred at room temperature for 10 min, and cyclopropionyl chloride (0.18 g, 1.72 mmol) was added dropwise. The reaction mixture was allowed to react overnight at room temperature. The reaction solution was washed with saturated sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate, and then evaporated to dryness under reduced pressure. The residue was purified by column chromatography (eluent: hexane: ethyl acetate = 10:1) to give a white solid (0.49 g, 44.57%).

[0329] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.31 (s, 1H), 8.61 (s, 1H), 8.09 (dd, J = 7.7, 4.2Hz, 3H), 7.83 (t, J = 6.7Hz, 1H), 7.45–7.33 (m, 4H), 1.42 (ddd, J = 12.1, 7.8, 4.4Hz, 1H), 0.99–0.92 (m, 2H), 0.91–0.84 (m, 2H).

[0330] ESI-MS (m / z): [MH-] Theoretical value: 733.0002, Measured value: 733.0012.

[0331] (6) Synthesis of N-(2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)-N-(cyclopropanecarbonyl)-3-(N-(cyclopropanecarbonyl)-4-fluorobenzamido)-2-fluorobenzamide

[0332]

[0333] N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-N-(cyclopropanecarbonyl)-2-fluoro-3-(4-fluorobenzamido)benzamide (1.00 g, 1.36 mmol) was dissolved in ultra-dry tetrahydrofuran. Sodium hydride (0.07 g, 2.72 mmol) was added in portions, and the mixture was stirred in an ice bath for 30 min. Cyclopropylformyl chloride (0.21 g, 2.04 mmol) was then added, and the reaction was allowed to proceed at room temperature for 2.5-3.5 h. After the reaction was complete, the mixture was evaporated to dryness, and dichloromethane was added. The mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated brine, and dried over anhydrous sodium sulfate. The mixture was then evaporated to dryness under reduced pressure and purified by silica gel column chromatography to give a light pink solid (0.57 g, 52.29%).

[0334] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 8.61 (s, 1H), 8.10 (s, 1H), 7.76 (dd, J = 8.6, 5.6Hz, 3H), 7.57 (t, J = 6.5Hz, 1H), 7.41 (t, J = 7.9Hz, 1H), 7.33–7.26 (m, 2H), 1.94 (ddd, J = 12.4, 7.5, 5.1Hz, 1H), 1.44–1.34 (m, 1H), 1.01–0.86 (m, 8H).

[0335] ESI-MS (m / z): [M+Na] + Theoretical value: 827.0214, measured value: 827.0200.

[0336] Example 15

[0337] Preparation methods of compound number 1123 in Table 1:

[0338]

[0339] N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-N-(cyclopropanecarbonyl)-2-fluoro-3-(4-fluorobenzamido)benzamide (1.00 g, 1.36 mmol) was dissolved in ultra-dry tetrahydrofuran. Sodium hydride (0.07 g, 2.72 mmol) was added in portions, and the mixture was stirred in an ice bath for 30 min. Acryloyl chloride (0.18 g, 2.04 mmol) was added, and the reaction was allowed to proceed at room temperature for 2.5-3.5 h. After the reaction was complete, the mixture was evaporated to dryness, and dichloromethane was added. The mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated brine, and dried over anhydrous sodium sulfate. The mixture was then evaporated to dryness under reduced pressure and purified by silica gel column chromatography to give a light pink solid (0.38 g, 35.51%).

[0340] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 8.60 (s, 1H), 8.09 (s, 1H), 7.78–7.67 (m, 3H), 7.55 (t, J = 6.3 Hz, 1H), 7.38 (t, J = 7.9 Hz, 1H), 7.32–7.24 (m, 2H), 6.59 (dd, J = 16.9, 10.3 Hz, 1H), 6.35 (dd, J = 16.9, 1.5 Hz, 1H), 5.92 (dd, J = 10.3, 1.5 Hz, 1H), 1.36 (d, J = 6.5 Hz, 1H), 0.93–0.86 (m, 4H).

[0341] ESI-MS (m / z): [M+Na] + Theoretical value: 811.0078, measured value: 811.0074.

[0342] Example 16

[0343] Preparation method of compound number 1124 in Table 1:

[0344]

[0345] N-(2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)-N-(cyclopropanecarbonyl)-2-fluoro-3-(4-fluorobenzamido)benzamide (1.00 g, 1.36 mmol) was dissolved in ultra-dry tetrahydrofuran. Sodium hydride (0.07 g, 2.72 mmol) was added in portions, and the mixture was stirred in an ice bath for 30 min. Methoxyacetyl chloride (0.22 g, 2.04 mmol) was then added, and the reaction was allowed to proceed at room temperature for 2.5-3.5 h. After the reaction was complete, the mixture was evaporated to dryness, and dichloromethane was added. The mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated brine, and dried over anhydrous sodium sulfate. The mixture was then evaporated to dryness under reduced pressure and purified by silica gel column chromatography to give a white solid (0.61 g, 55.45%).

[0346] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 8.60 (d, J = 1.3Hz, 1H), 8.09 (s, 1H), 7.70-7.62 (m, 3H), 7.53 (t, J = 6.4Hz, 1H), 7.34 (t, J = 7.9Hz, 1H), 7.25-7.18 (m, 2H), 4.49 (s, 2H), 3.34 (s, 3H), 1.35 (d, J = 4.9Hz, 1H), 0.89 (ddd, J = 11.3, 7.6, 3.6Hz, 4H).

[0347] ESI-MS (m / z): [M+Na]+ Theoretical value: 829.0183, measured value: 829.0176.

[0348] Example 17

[0349] Preparation methods of compound number 1141 in Table 1: (1) Synthesis of N-(3-((2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-2-chloronicotinamide

[0350]

[0351] 3-Amino-N-(2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide (1.20 g, 2.20 mmol) was added to 5 ml of acetonitrile, the temperature was raised to 80 °C, and 2-chloronicotinyl chloride (0.39 g, 2.21 mmol) was added. The reaction mixture was reacted for 2 h. The reaction solution was evaporated to dryness under reduced pressure, dissolved in ethyl acetate solution, washed with saturated potassium carbonate and saturated brine, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The residue was purified by column chromatography (eluent: hexane: ethyl acetate = 10:1) to give a pale yellow solid (1.20 g, yield 79.75%).

[0352] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 10.81 (s, 1H), 10.75 (s, 1H), 8.55 (dd, J = 4.8, 1.8Hz, 1H), 8.44 (s, 1H), 8.17 (q, J = 7.3Hz, 1H), 8.10 (dd, J = 7.5, 1.8Hz, 1H), 7.98 (s, 2H), 7.61–7.52 (m, 2H), 7.43 (t, J = 7.9Hz, 1H).

[0353] ESI-MS (m / z): [MH-] Theoretical value: 683.9376, Measured value: 683.9371.

[0354] (2) Synthesis of N-(3-((2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)(cyclopropanecarbonyl)carbamoyl)-2-fluorophenyl)-2-chloro-N-(cyclopropanecarbonyl)nicotinamide

[0355]

[0356] N-(3-((2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-2-chloronicotinamide (1.00 g, 1.46 mmol) was dissolved in acetonitrile, and triethylamine (0.44 g, 4.38 mmol) was added. The mixture was heated to 60 °C, and cyclopropylformyl chloride (0.46 g, 4.38 mmol) was added. The reaction was allowed to proceed for 2.5 h–3.5 h. After the reaction was complete, the mixture was evaporated to dryness, and dichloromethane was added. The mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated brine, and dried over anhydrous sodium sulfate. The mixture was then evaporated to dryness under reduced pressure and purified by silica gel column chromatography to give a white solid (0.83 g, 69.17%).

[0357] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 8.62 (s, 1H), 8.48 (dd, J=4.8, 1.9Hz, 1H), 8.14–8.04 (m, 2H), 7.94–7.86 (m, 1H), 7.72–7.62 (m, 1H), 7.57–7.47 (m, 2H), 1.76–1.66 (m, 1H), 1.46–1.37 (m, 1H), 0.97–0.84 (m, 8H).

[0358] ESI-MS(m / z):[M+H + Theoretical value: 822.0051, measured value: 822.0033.

[0359] Example 18

[0360] Preparation method of compound number 1142 in Table 1:

[0361]

[0362] N-(3-((2-bromo-4-(perfluoropropane-2-yl)-6-(trifluoromethyl)phenyl)carbamoyl)-2-fluorophenyl)-2-chloronicotinamide (1.00 g, 1.46 mmol) was dissolved in acetonitrile, and triethylamine (0.44 g, 4.38 mmol) was added. The mixture was heated to 60 °C, and acryloyl chloride (0.40 g, 4.38 mmol) was added. The reaction was allowed to proceed for 2.5–3.5 h. After the reaction was completed, the mixture was evaporated to dryness, and dichloromethane was added. The mixture was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated brine, and dried over anhydrous sodium sulfate. The mixture was then evaporated to dryness under reduced pressure and purified by silica gel column chromatography to give a white solid (0.51 g, 43.97%).

[0363] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 8.59 (s, 1H), 8.50 (dd, J = 4.8, 1.8Hz, 1H), 8.11 (dd, J = 7.6, 1.7Hz, 2H), 7.86 (dd, J = 10.8, 4.3Hz, 1H), 7.68 (t, J = 6.5Hz, 1H), 7.57-7.46 (m, 2H), 6.51-6.34 (m, 3H), 6.09 (dd, J = 16.3, 10.3Hz, 1H), 6.01-5.88 (m, 2H).

[0364] ESI-MS (m / z): [M+Na] + Theoretical value: 813.9578, measured value: 813.9572.

[0365] Example 19

[0366] Preparation methods of compound number 1157 in Table 1: (1) Synthesis of 3-(2-chlorobenzamido)-2-fluoro-N-(2-methyl-4-(perfluoropropane-2-yl)phenyl)benzamide

[0367]

[0368] 3-Amino-2-fluoro-N-(2-methyl-4-(perfluoropropane-2-yl)phenyl)benzamide (3.00 g, 7.28 mmol) was dissolved in acetonitrile, and 2-chlorobenzoyl chloride (1.27 g, 7.28 mmol) was added. The mixture was reacted at 80 °C for 2 h. The crude product was evaporated to dryness and, without further processing, was a pale yellow solid (3.26 g, yield 81.30%).

[0369] The 1H NMR spectrum (400MHz, DMSO-d6) of the compound is as follows (δ[ppm]): δ 10.55 (s, 1H), 10.16 (s, 1H), 8.04 (s, 1H), 7.85 (d, J = 6.7Hz, 1H), 7.48 (dd, J = 43.5, 37.0Hz, 8H), 2.40 (s, 3H).

[0370] (2) Synthesis of 3-(2-chloro-N-(cyclopropanecarbonyl)benzamido)-N-(cyclopropanecarbonyl)-2-fluoro-N-(2-methyl-4-(perfluoropropane-2-yl)phenyl)benzamide

[0371]

[0372] 3-(2-chlorobenzamido)-2-fluoro-N-(2-methyl-4-(perfluoropropane-2-yl)phenyl)benzamide (1.00 g, 1.82 mmol) was dissolved in ultra-dry tetrahydrofuran, and sodium hydride (0.09 g, 3.64 mmol) was added in portions. The mixture was stirred in an ice bath for 30 min, and then cyclopropylformyl chloride (0.57 g, 5.46 mmol) was added. The reaction was allowed to proceed at room temperature for 2.5-3.5 h. After the reaction was complete, the solution was evaporated to dryness, and dichloromethane was added. The solution was washed successively with dilute hydrochloric acid (2 mol / L), saturated sodium carbonate solution, and saturated brine, and dried over anhydrous sodium sulfate. The solution was then evaporated to dryness under reduced pressure and purified by silica gel column chromatography to give a light pink solid (0.55 g, 44.00%).

[0373] The 1H NMR spectrum (500MHz, DMSO-d6) of the compound is as follows (δ [ppm]): δ 7.79-7.62 (m, 5H), 7.56 (dd, J=7.4, 1.6Hz, 1H), 7.52-7.37 (m, 4H), 2.34 (s, 3H), 1.77-1.68 (m, 1H), 1.55-1.46 (m, 1H), 0.96-0.83 (m, 8H).

[0374] ESI-MS (m / z): [M+Na] + Theoretical value: 709.1116, measured value: 709.1108.

[0375] Effect Example

[0376] Some of the compounds listed in this application were tested for activity against a variety of pests.

[0377] (1) Assay for the activity of rice stem borer:

[0378] Preparation of compound solution: Weigh 10 mg of the original drug using a balance, prepare a 1% stock solution with DMF, and then dilute it with distilled water containing 0.1% Tween-80 to prepare four test concentrations of 5 mg / L, 3.0 mg / L, 1.5 mg / L, and 0.75 mg / L for later use.

[0379] The immersion method was used. After soaking the water chestnut slices in the medicine for 10 seconds, they were placed in a plastic box lined with filter paper and air-dried naturally. Ten third-instar rice stem borers were placed in each box and observed in a room with 26°C light exposure for 16 hours and darkness for 8 hours. The number of dead insects was observed after 4 days.

[0380] The control compound CK01 is shown in formula (III), the control compound CK02 is shown in formula (IV), the control compound CK03 is shown in formula (V), and the control compound CK04 is shown in formula (VI):

[0381]

[0382] Compounds 5, 11, 25, 146, 147, 155, 156, 170, 171, 339, 345, 483, 489, 491, 492, 506, 507, 677, 681, 682, 683, 777, 791, 971, 972, 973, 978, 979, 992, 1001, 1122, 1140, and 1152 showed a lethality of over 80% against rice stem borer after 4 days at a concentration of 10 mg / L. Then, low-concentration activity tests were conducted on compounds 147, 156, 171, 492, 507, 677, 683, 777, 791, 992, CK01, CK02, CK03, and CK04, and the results are shown in Table 2.

[0383] Table 2: Results of activity assays on rice stem borer for some compounds in Table 1.

[0384]

[0385] Note: Compound numbers correspond to those in Table 1.

[0386] (2) Activity assay of diamondback moth:

[0387] Preparation of compound solution: Weigh 10 mg of the original drug using a balance, prepare a 1% stock solution with DMF, and then dilute it with distilled water containing 0.1% Tween-80 to prepare four test concentrations of 3 mg / L, 1 mg / L, 0.5 mg / L and 0.1 mg / L for later use.

[0388] The immersion method was used. After soaking the leaves of Chinese cabbage in the medicine for 10 seconds, they were placed in a plastic box lined with filter paper and allowed to air dry naturally. Ten third-instar diamondback moths were inoculated into each box. The boxes were placed in an observation room at 26℃ with 16 hours of light and 8 hours of darkness. The number of dead insects was observed after 3 days.

[0389] Compounds 5, 11, 25, 146, 147, 155, 156, 170, 171, 339, 345, 483, 489, 491, 492, 506, 507, 677, 681, 682, 683, 777, 791, 971, 972, 973, 978, 979, 992, 1001, 1122, 1140, and 1152 all showed a mortality rate of over 90% against diamondback moth after 3 days at a concentration of 3 mg / L. Then, low-concentration activity tests were conducted on compounds 147, 156, 171, 492, 507, 677, 683, 777, 791, 992, CK01, CK02, CK03, and CK04, and the results are shown in Table 3.

[0390] Table 3: Results of activity assays on diamondback moth for some compounds listed in Table 1.

[0391]

[0392]

[0393] Note: Compound numbers correspond to those in Table 1.

[0394] The results show that the m-diamid compounds provided by this invention exhibit high bioactivity against both rice stem borer and diamondback moth, and these m-diamid compounds show no cross-resistance with chlorantraniliprole. Furthermore, a comparison of the embodiments of this application with CK01, CK02, CK03, and CK04 in Tables 2 and 3 shows that this application, through the selection of suitable groups for R1 and R2, and the synergistic effect of suitable groups between R1 and R2, can enhance the lipophilicity of the m-diamid compounds. When applied to the insecticidal field, these compounds are more easily absorbed by pests, thus exhibiting better insecticidal activity. In addition, this application, through a special design of the structure of the m-diamid compounds and the grafting positions of R1 and R2, makes the m-diamid compounds more lipophilic, which can further enhance their insecticidal efficacy. In pesticide organic small molecule compounds, due to differences in the type of substituents, group volume, and electronegativity, the metabolic and transport properties of the entire molecule in the organism can vary greatly, resulting in significant differences in biological activity. Furthermore, the metabolic properties, transport properties, and ability of the molecule to bind to receptors are unpredictable and require a great deal of creative work to determine.

[0395] The preferred embodiments have been described in detail above, but the present invention is not limited to the specific implementation methods described above. Those skilled in the art can make various specific modifications under the guidance of this application without departing from the scope of protection of this application, and these modifications all fall within the scope of protection of the present invention.

Claims

1. A m-diamide compound as shown in formula (Ⅰ): (Ⅰ) In formula (Ⅰ), Q is any one of substituted or unsubstituted phenyl or substituted or unsubstituted pyridyl, wherein the substituted phenyl or substituted pyridyl group is selected from halogen or cyano groups; R1 is any one of C3-C5 cycloalkyl, C2-C5 alkenyl, and C2-C6 alkynyl; Or it may be a group represented by -L1-M-L2, wherein, L1 is an unsubstituted C1-C3 alkylene group; M is an oxygen atom; L2 is a C1-C3 alkyl group; R2 is a hydrogen atom or a C3-C5 cycloalkyl carbonyl group; X1 and X2 are each independently selected from hydrogen atoms or fluorine atoms, and X1 and X2 are not both hydrogen atoms at the same time; Y1 and Y3 are each independently selected from hydrogen atoms, bromine atoms, methyl groups, or trifluoromethyl groups; Y2 is a C2-C6 fluoroalkyl group; W represents an oxygen atom.

2. The m-diamide compound as described in claim 1, characterized in that, X1 is a fluorine atom, and X2 is a hydrogen atom; Y1 and Y3 are independently bromine, methyl, or trifluoromethyl atom, respectively; Y2 is pentafluoroethyl, heptafluoroisopropyl, or nonafluoro-2-butyl.

3. A pesticide-acceptable salt of a meta-diamide compound as described in claim 1 or 2.

4. The use of a pesticide-acceptable salt of a m-diamide compound as described in claim 1 or 2, or a m-diamide compound as described in claim 3, in the preparation of an insecticide in the agricultural, forestry, or health fields.

5. An insecticide formulation, characterized in that, The insecticide comprises an active ingredient and excipients; the active ingredient comprises a pesticide-acceptable salt of a m-diamide compound as described in claim 1 or 2 and / or a m-diamide compound as described in claim 3; the active ingredient in the insecticide formulation has a mass percentage of 0.1%-99%.

6. An insecticide composition, characterized in that, The insecticide composition comprises an active ingredient and other active compounds; the active ingredient is a pesticide-acceptable salt of a m-diamid compound as described in claim 1 or 2 and / or a m-diamid compound as described in claim 3; the other active compounds are selected from one or more of insecticides, poison baits, disinfectants, acaricides, nematicides, fungicides, growth regulators, and herbicides; the active ingredient in the insecticide composition has a mass percentage of 1%-99%.

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