Aromatic heterocyclic compound and / or salt thereof, preparation method and application of aromatic heterocyclic compound and / or salt thereof, and insecticidal and acaricidal agent

Abstract

The invention relates to an aromatic heterocyclic compound and / or a salt thereof, a preparation method and application thereof, and an insecticidal and acaricidal agent. The aromatic heterocyclic compound has a structure as shown in a formula (I). The aromatic heterocyclic compound provided by the invention can have an acaricidal effect when being used at a low concentration content, meanwhile, the provided compound has relatively good safety, and in a rat acute toxicity test, part of the compound does not show obvious toxicity under the administration dosage of 1,000 mg / kg. # imgabs0 #

Description

Aromatic heterocyclic compound and / or its salt, preparation method and application thereof, and insecticide and acaricide

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of Chinese patent application 202311251021.6 filed on September 26, 2023 and Chinese patent application 202311762666.6 filed on December 20, 2023, the contents of which are incorporated herein by reference. Technical Field

[0003] The present invention relates to the technical field of pesticides, and in particular to an aromatic heterocyclic compound and / or its salt, a preparation method and application thereof, and an insecticide and acaricide. Background Art

[0004] In crop production in agriculture and horticulture, losses caused by pests and other factors continue to be significant. Furthermore, pests resistant to existing pesticides are emerging. From the perspectives of impact on environmental organisms and labor conservation, there is a desire to develop insecticides and acaricides for agricultural and horticultural use that have novel properties, minimal impact on natural enemies and beneficial insects, and possess penetrating and translocation activities.

[0005] CN114957131A discloses a benzimidazole compound having excellent insecticidal and acaricidal effects, and in particular, some compounds have good acaricidal activity at a low dose of 6.25 mg / L.

[0006] However, due to the high resistance development speed of pests and mites and the national requirement to reduce pesticide use, it is still necessary to develop new compounds with higher activity so that they can produce excellent killing effects on pests and mites at lower concentrations.

[0007] Summary of the Invention

[0008] The purpose of the present invention is to overcome the defect that existing aromatic heterocyclic compounds can only have insecticidal and acaricidal activity when used at high concentrations, which is difficult to meet the demand for controlling field pest mites. The present invention provides a new aromatic heterocyclic compound and its salt, which can be used as an active ingredient in an insecticide and acaricide, and can have a high control effect when used at a low concentration (not higher than 100 ppm).

[0009] In order to achieve the above object, the first aspect of the present invention provides an aromatic heterocyclic compound and / or its salt, wherein the aromatic heterocyclic compound has a structure shown in formula (I):

[0010] wherein R is selected from substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted phenyl, wherein the substituted substituents are each independently selected from halogen, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 cycloalkoxy;

[0011] X 1 Select N or CY 1 , X 2 Select N or CY 2 , X 3 Select N or CY 3 , X 4 Select N or CY 4 ; where X 1 、X 2 、X 3 and X 4 At least one of them is selected from N;

[0012] Y 1 、Y 2 、Y 3 、Y 4 are independently selected from H, halogen, CN, NO2, formyl, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Alkylthio, substituted or unsubstituted C1-C 10 Alkylsulfinyl, substituted or unsubstituted C1-C 10 Alkylsulfonyl, substituted or unsubstituted C1-C 10 Alkylcarbonyl, substituted or unsubstituted C1-C 10 substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C2-C6 alkenyloxy, substituted or unsubstituted C2-C6 alkynyloxy, substituted or unsubstituted C1-C 10 Alkylcarbonyloxy, substituted or unsubstituted C1-C 10 Cyanoalkyl, substituted or unsubstituted C1-C10 substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryl C1-C6 alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C1-C6 alkoxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylthio, substituted or unsubstituted aryl C1-C6 alkylsulfonyl, substituted or unsubstituted aryl C1-C6 alkylsulfinyl, substituted or unsubstituted aryl C1-C6 alkylthio, substituted or unsubstituted heterocycle, substituted or unsubstituted heterocycle C1-C6 alkyl, substituted or unsubstituted heterocycleoxy, wherein each group of the substituted substituents is independently selected from halogen, unsubstituted C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 At least one of cycloalkoxy; optionally, Z 1 and Z 2 , Z 2 and Z 3 , Z 3 and Z 4 They can be divided into three groups, at least one of which is cyclized with the pyridine ring in formula (I) via or without at least one heteroatom to form at least one 3- to 8-membered ring.

[0013] Q is selected from the following aromatic rings:

[0014] In Q1, Z 1 Select N or CT 1 , Z 2 Select N or CT 2 , Z 3 Select N or CT 3 , Z 4 Select N or CT 4 , Z 5 Select N or CT 5 ; In the Q1 ring, the number of N atoms does not exceed 4;

[0015] In Q2, Z 1 Selected from N, NR 1 , O, S or CT 1 , Z 2 Selected from N, NR 2 , O, S or CT 2, Z 3 Selected from N, NR 3 , O, S or CT 3 , Z 4 Selected from N, NR 4 , O, S or CT 4 ; In the Q2 ring, the number of O or S atoms does not exceed 1;

[0016] In Q3, Z 1 Selected from N, NR 1 , O, S or CT 1 , Z 2 Selected from N, NR 2 , O, S or CT 2 , Z 3 Selected from N, NR 3 , O, S or CT 3 , Z 4 Selected from N, NR 4 , O, S or CT 4 ; In the Q3 ring, the number of O or S atoms does not exceed 1, and the number of N atoms does not exceed 4;

[0017] T 1 、T 2 、T 3 、T 4 、T 5 are independently selected from H, halogen, CN, NO2, formyl, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Alkylthio, substituted or unsubstituted C1-C 10 Alkylsulfinyl, substituted or unsubstituted C1-C 10 Alkylsulfonyl, substituted or unsubstituted C1-C 10 Alkylcarbonyl, substituted or unsubstituted C1-C 10 Alkoxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C2-C6 alkenyloxy, substituted or unsubstituted C2-C6 alkynyloxy, substituted or unsubstituted C1-C 10 Alkylcarbonyloxy, substituted or unsubstituted C1-C 10 Cyanoalkyl, substituted or unsubstituted C1-C 10substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryl C1-C6 alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C1-C6 alkoxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylthio, substituted or unsubstituted aryl C1-C6 alkylsulfonyl, substituted or unsubstituted aryl C1-C6 alkylsulfinyl, substituted or unsubstituted aryl C1-C6 alkylthio, substituted or unsubstituted heterocycle, substituted or unsubstituted heterocycle C1-C6 alkyl, substituted or unsubstituted heterocycleoxy, wherein the substituted substituents are each independently selected from halogen, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 Cycloalkoxy; optionally, T 1 and T 2 、T 2 and T 3 、T 3 and T 4 、T 4 and T 5 It can be divided into four groups, wherein at least one group of carbon atoms to which it is attached is cyclized via or without at least one heteroatom to form at least one 3- to 8-membered ring;

[0018] R 1 、R 2 、R 3 and R 4Each independently selected from H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C1-C6 alkylsulfinyl, substituted or unsubstituted C1-C6 alkylsulfonyl or substituted or unsubstituted phenyl; wherein the substituted substituents are each independently selected from halogen, CN, NO2, formyl, C1-C6 alkyl, halogenated C1-C6 alkyl, -At least one of a C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C3-C6 cycloalkyl group, a C1-C6 alkoxy group, a halogenated C1-C6 alkoxy group, a C3-C6 cycloalkyloxy group, a halogenated C3-C6 cycloalkoxy group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C1-C6 alkylcarbonyloxy group or a cyano C1-C6 alkoxy group.

[0019] A second aspect of the present invention provides a method for preparing an aromatic heterocyclic compound and / or a salt thereof, the method comprising:

[0020] (1) in a first solvent, in the presence of a first alkaline substance and a condensing agent, subjecting compound V and compound IV to a condensation reaction to obtain compound III;

[0021] (2) in a second solvent, subjecting the compound III' to a cyclization reaction with an acidic substance to obtain compound II;

[0022] (3) in a third solvent, in the presence of a second alkaline substance, subjecting the compound II to a sulfonylation reaction with a sulfonyl-containing compound to obtain compound I;

[0023] Wherein, the compound V has a structure represented by formula (V), the compound IV' has a structure represented by formula (IV), the compound III has a structure represented by formula (III), the compound II' has a structure represented by formula (II), the compound I has a structure represented by formula (I), and the sulfonyl-containing compound has a structure represented by formula (VI);

[0024] In formula (I), formula (II), formula (III), formula (IV), formula (V) and formula (VI), R, X 1 、X 2 、X 3 、X 4 , Q is defined as the same as in any one of claims 1-4, and L is selected from halogen.

[0025] The third aspect of the present invention provides the use of at least one of the aromatic heterocyclic compounds and / or salts thereof, and pyridimidazole compounds or salts thereof described in the first aspect of the present invention in the preparation of insecticides and acaricides.

[0026] The fourth aspect of the present invention provides an insecticide and acaricide, which contains an active ingredient, and the active ingredient is selected from at least one of the aromatic heterocyclic compounds and / or salts thereof, and pyridimidazole compounds or salts thereof described in the first aspect of the present invention.

[0027] The fifth aspect of the present invention provides the use of the insecticide and acaricide according to the fourth aspect of the present invention in killing insects and / or acaricides in agriculture, forestry and gardening.

[0028] Compared with the prior art, the present invention has at least the following advantages:

[0029] The aromatic heterocyclic compounds or salts thereof provided by the present invention are used as active ingredients as insecticides and acaricides. When used at low concentrations, they can have excellent control effects. At the same time, the compounds provided by the present invention have good safety. In the acute toxicity test in rats, the compounds of the present invention did not show obvious toxicity at a dose of 1000 mg / kg.

[0030] Other features and advantages of the present invention will be described in detail in the following detailed description. DETAILED DESCRIPTION

[0031] The endpoints of the ranges and any values ​​disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoints of each range, the endpoints of each range and individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered to be specifically disclosed herein.

[0032] In this invention, the terms involved are interpreted as follows:

[0033] Halogen refers to fluorine, chlorine, bromine and iodine.

[0034] Alkyl refers to an alkyl group in the form of a straight chain or branched chain, excluding cycloalkyl. The C1-C8 alkyl refers to an alkyl group having 1-8 carbon atoms, including but not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, etc.

[0035] Cycloalkyl refers to an alkyl group containing a cyclic chain, and the C1-C8 cycloalkyl refers to a cycloalkyl group having 1-8 carbon atoms, including but not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.

[0036] Alkenyl refers to a straight chain or branched alkenyl group, and the C2-C8 alkenyl group refers to an alkenyl group having 2 to 8 carbon atoms, including but not limited to 1-propenyl, 2-propenyl and different butenyl, pentenyl and hexenyl isomers; alkenyl also includes polyenes, such as 1,2-propadienyl and 2,4-hexadienyl.

[0037] Alkynyl refers to a straight chain or branched alkynyl group, and the C2-C8 alkynyl group refers to an alkynyl group having 2-8 carbon atoms, including but not limited to 1-propynyl, 2-propynyl and different butynyl, pentynyl and hexynyl isomers; alkynyl also includes groups containing multiple triple bonds, such as 2,5-hexadiynyl.

[0038] Alkoxy refers to a group in which an oxygen atom is attached to the terminal of a straight or branched alkyl group. 1-8 The alkoxy group refers to an alkoxy group having 1 to 8 carbon atoms, including but not limited to methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy and the like.

[0039] Cycloalkoxy is a group containing an oxygen atom in a cycloalkyl group. 1-8 The cycloalkoxy group refers to a cycloalkoxy group having 1 to 8 carbon atoms, including but not limited to cyclopropyloxy, cyclobutyloxy, etc.

[0040] Alkylthio refers to a group with a sulfur atom attached to the end of an alkyl group, including but not limited to methylthio, ethylthio, n-propylthio, isopropylthio, tert-butylthio and the like.

[0041] The alkylsulfinyl group refers to a group with a sulfinyl group attached to the end of an alkyl group, including but not limited to methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, tert-butylsulfinyl and the like.

[0042] The alkylsulfonyl group refers to a group with a sulfonyl group attached to the end of an alkyl group, including but not limited to methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, tert-butylsulfonyl and the like.

[0043] A haloalkyl group, a haloalkenyl group, a haloalkynyl group, a halocycloalkyl group, a haloalkoxy group, a halocycloalkoxy group, a haloalkylthio group, a haloalkylsulfinyl group, and a haloalkylsulfonyl group refer to groups in which at least one hydrogen atom in an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an alkylthio group, an alkylsulfinyl group, or an alkylsulfonyl group is substituted by a halogen atom. When there are two or more halogen atoms, the halogen atoms may be the same or different.

[0044] In the present invention, cycloalkyl-substituted alkyl, halocycloalkyl-substituted alkyl, cycloalkyl-substituted haloalkyl, alkoxy-substituted alkyl, haloalkoxy-substituted alkyl, alkoxy-substituted haloalkyl, cycloalkoxy-substituted alkyl, halocycloalkoxy-substituted alkyl, and cycloalkoxy-substituted haloalkyl respectively mean that at least one hydrogen atom in the alkyl group is replaced by a cycloalkyl group, a halocycloalkyl group, an alkoxy group, a haloalkoxy group, a cycloalkoxy group, or a halocycloalkoxy group.

[0045] In the present invention, heteroatoms include but are not limited to O, S, and N atoms.

[0046] Other groups have similar definitions as above, except for the different substituents or the number of carbon atoms, and will not be described in detail.

[0047] Other terms in the present invention may be interpreted in a conventional manner in the art.

[0048] As mentioned above, the first aspect of the present invention provides an aromatic heterocyclic compound and / or its salt, wherein the aromatic heterocyclic compound has a structure shown in formula (I):

[0049] wherein R is selected from substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted phenyl, wherein the substituted substituents are each independently selected from halogen, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 cycloalkoxy;

[0050] X 1 Select N or CY 1 , X 2 Select N or CY 2 , X 3 Select N or CY 3 , X 4 Select N or CY 4 ; where X 1 、X 2 、X 3 and X 4 At least one of them is selected from N;

[0051] Y 1 、Y 2 、Y 3 、Y 4 are independently selected from H, halogen, CN, NO2, formyl, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Alkylthio, substituted or unsubstituted C1-C 10 Alkylsulfinyl, substituted or unsubstituted C1-C 10 Alkylsulfonyl, substituted or unsubstituted C1-C 10 Alkylcarbonyl, substituted or unsubstituted C1-C 10 substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C2-C6 alkenyloxy, substituted or unsubstituted C2-C6 alkynyloxy, substituted or unsubstituted C1-C 10 Alkylcarbonyloxy, substituted or unsubstituted C1-C 10 Cyanoalkyl, substituted or unsubstituted C1-C 10 substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryl C1-C6 alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C1-C6 alkoxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylthio, substituted or unsubstituted aryl C1-C6 alkylsulfonyl, substituted or unsubstituted aryl C1-C6 alkylsulfinyl, substituted or unsubstituted aryl C1-C6 alkylthio, substituted or unsubstituted heterocycle, substituted or unsubstituted heterocycle C1-C6 alkyl, substituted or unsubstituted heterocycleoxy, wherein each group of the substituted substituents is independently selected from halogen, unsubstituted C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 At least one of cycloalkoxy; optionally, Y 1 and Y 2 、Y 2 and Y3 、Y 3 and Y 4 、Y 4 and Y 5 Can be divided into four groups, at least one of which is the same as X in formula (I) 1 To X 4 The aromatic rings formed together are cyclized via or without at least one heteroatom to form at least one 3- to 8-membered ring;

[0052] Q is selected from the following aromatic rings:

[0053] In Q1, Z 1 Select N or CT 1 , Z 2 Select N or CT 2 , Z 3 Select N or CT 3 , Z 4 Select N or CT 4 , Z 5 Select N or CT 5 ; In the Q1 ring, the number of N atoms does not exceed 4;

[0054] In Q2, Z 1 Selected from N, NR 1 , O, S or CT 1 , Z 2 Selected from N, NR 2 , O, S or CT 2 , Z 3 Selected from N, NR 3 , O, S or CT 3 , Z 4 Selected from N, NR 4 , O, S or CT 4 ; In the Q2 ring, the number of O or S atoms does not exceed 1;

[0055] In Q3, Z 1 Selected from N, NR 1 , O, S or CT 1 , Z 2 Selected from N, NR 2 , O, S or CT 2 , Z 3 Selected from N, NR 3 , O, S or CT 3 , Z 4 Selected from N, NR 4 , O, S or CT 4 ; In the Q3 ring, the number of O or S atoms does not exceed 1, and the number of N atoms does not exceed 4;

[0056] T1 、T 2 、T 3 、T 4 、T 5 are independently selected from H, halogen, CN, NO2, formyl, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Alkylthio, substituted or unsubstituted C1-C 10 Alkylsulfinyl, substituted or unsubstituted C1-C 10 Alkylsulfonyl, substituted or unsubstituted C1-C 10 Alkylcarbonyl, substituted or unsubstituted C1-C 10 Alkoxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C2-C6 alkenyloxy, substituted or unsubstituted C2-C6 alkynyloxy, substituted or unsubstituted C1-C 10 Alkylcarbonyloxy, substituted or unsubstituted C1-C 10 Cyanoalkyl, substituted or unsubstituted C1-C 10 substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryl C1-C6 alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C1-C6 alkoxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylthio, substituted or unsubstituted aryl C1-C6 alkylsulfonyl, substituted or unsubstituted aryl C1-C6 alkylsulfinyl, substituted or unsubstituted aryl C1-C6 alkylthio, substituted or unsubstituted heterocycle, substituted or unsubstituted heterocycle C1-C6 alkyl, substituted or unsubstituted heterocycleoxy, wherein the substituted substituents are each independently selected from halogen, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 Cycloalkoxy; optionally, T 1 and T 2 、T 2 and T 3 、T3 and T 4 、T 4 and T 5 It can be divided into four groups, wherein at least one group of carbon atoms to which it is attached is cyclized via or without at least one heteroatom to form at least one 3- to 8-membered ring;

[0057] R 1 、R 2 、R 3 and R 4 Each independently selected from H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C1-C6 alkylsulfinyl, substituted or unsubstituted C1-C6 alkylsulfonyl or substituted or unsubstituted phenyl; wherein the substituted substituents are each independently selected from halogen, CN, NO2, formyl, C1-C6 alkyl, halogenated C1-C6 alkyl, -At least one of a C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C3-C6 cycloalkyl group, a C1-C6 alkoxy group, a halogenated C1-C6 alkoxy group, a C3-C6 cycloalkyloxy group, a halogenated C3-C6 cycloalkoxy group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C1-C6 alkylcarbonyloxy group or a cyano C1-C6 alkoxy group.

[0058] In the present invention, it means that Represents a large π bond.

[0059] In some embodiments of the present invention, preferably, R is selected from substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted phenyl, wherein the substituted substituents are each independently selected from at least one of halogen, C1-C3 alkyl, halo-substituted C1-C3 alkyl, C3-C6 cycloalkyl, halo-substituted C3-C6 cycloalkyl, C1-C3 alkoxy, halo-substituted C1-C3 alkoxy, C3-C6 cycloalkoxy or halo-substituted C3-C6 cycloalkoxy;

[0060] In some embodiments of the present invention, preferably, Y 1 、Y 2 、Y 3 、Y 4Each is independently selected from H, halogen, CN, NO2, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl substituted C1-C6 alkyl, halogenated C3-C6 cycloalkyl substituted C1-C6 alkyl, C3-C6 cycloalkyl substituted halogenated C1-C6 alkyl, C1-C6 alkoxy substituted C1-C6 alkyl, halogenated C1-C6 alkoxy substituted C1-C6 alkyl, C1-C6 alkoxy substituted halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkyl substituted C C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl substituted halogenated C3-C6 cycloalkyl, C1-C6 alkyl substituted halogenated C3-C6 cycloalkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C1-C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, formyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxy C2-C6 alkyl, alkylcarbonyl, arylcarbonyl, aryloxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, halogenated C2-C6 alkenyloxy, halogenated C2-C6 alkynyloxy, C1-C8 alkylcarbonyloxy, halogenated C1-C6 alkylcarbonyloxy, cyano C1-C6 alkyl, cyano C1-C6 alkoxy, C1-C6 alkyl-substituted silyl, substituted or unsubstituted amino, aryl, aryl C1-C6 alkyl, aryloxy, aryl C1 -C6 alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C1-C6 alkylsulfonyl, aryl C1-C6 alkylsulfinyl, aryl C1-C6 alkylthio, heterocyclic C1-C6 alkyl, heterocyclic oxy, wherein the substituted substituents are each independently selected from at least one of halogen, C1-C6 alkyl, halo-substituted C1-C6 alkyl, C3-C6 cycloalkyl, halo-substituted C3-C6 cycloalkyl, C1-C6 alkoxy, halo-substituted C1-C6 alkoxy, C3-C6 cycloalkyloxy or halo-substituted C3-C6 cycloalkyloxy.

[0061] In some embodiments of the present invention, preferably, R is selected from C1-C4 alkyl or halogenated C1-C4 alkyl; or substituted or unsubstituted phenyl, wherein the substituted substituents are each independently selected from at least one of halogen, C1-C3 alkyl, halogenated C1-C3 alkyl, C1-C3 alkoxy, and halogenated C1-C3 alkoxy;

[0062] In some embodiments of the present invention, preferably, Y 1 、Y 2 、Y 3 、Y 4Each is independently selected from H, halogen, CN, NO2, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted amino, C1-C4 alkoxy C1-C4 alkyl, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C1-C6 -C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or halogenated C1-C6 alkylsulfonyl; wherein the substituted substituents are each independently selected from at least one of halogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C3-C6 cycloalkyloxy or halogenated C3-C6 cycloalkoxy.

[0063] In some embodiments of the present invention, preferably, in formula (I), R is selected from C1-C4 alkyl, halogenated C1-C4 alkyl or phenyl.

[0064] In some embodiments of the present invention, preferably, Y 1 、Y 2 、Y 3 、Y 4 Each independently selected from H, halogen, CN, NO2, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C1-C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or halogenated C1-C6 alkylsulfonyl.

[0065] In some embodiments of the present invention, preferably, Y 1 It is not a substituted or unsubstituted piperazine ring.

[0066] In some embodiments of the present invention, preferably, T 1 、T 2 、T 3 、T 4 、T 5Each is independently selected from H, halogen, CN, NO2, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl substituted C1-C6 alkyl, halogenated C3-C6 cycloalkyl substituted C1-C6 alkyl, C3-C6 cycloalkyl substituted halogenated C1-C6 alkyl, C1-C6 alkoxy substituted C1-C6 alkyl, halogenated C1-C6 alkoxy substituted C1-C6 alkyl, C1-C6 alkoxy substituted halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkyl substituted C3 -C6 cycloalkyl, halogenated C1-C6 alkyl-substituted C3-C6 cycloalkyl, C1-C6 alkyl-substituted halogenated C3-C6 cycloalkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C1-C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, formyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxy Carbonyl, arylcarbonyl, aryloxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, halogenated C2-C6 alkenyloxy, halogenated C2-C6 alkynyloxy, C1-C6 alkylcarbonyloxy, halogenated C1-C6 alkylcarbonyloxy, cyano C1-C6 alkyl, cyano C1-C6 alkoxy, C1-C6 alkyl-substituted silyl, substituted or unsubstituted amino, aryl, aryl C1-C6 alkyl, aryloxy, aryl C1- C6 alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C1-C6 alkylsulfonyl, aryl C1-C6 alkylsulfinyl, aryl C1-C6 alkylthio, heterocycle, heterocycle C1-C6 alkyl, heterocycleoxy, and the optional substituents are each independently selected from at least one of halogen, C1-C6 alkyl, halo-substituted C1-C6 alkyl, C3-C6 cycloalkyl, halo-substituted C3-C6 cycloalkyl, C1-C6 alkoxy, halo-substituted C1-C6 alkoxy, C3-C6 cycloalkyloxy or halo-substituted C3-C6 cycloalkyloxy.

[0067] In some embodiments of the present invention, preferably, T 1 、T 2 、T 3 、T 4 、T 5 Each is independently selected from H, halogen, CN, NO2, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C1-C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or halogenated C1-C6 alkylsulfonyl.

[0068] In some embodiments of the present invention, preferably, T 1 、T 2 、T 3 、T 4 、T 5 Each is independently selected from H, halogen, CN, NO2, CH3, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, cyclopropyl, CF3, CHF2, 2,2,2-trifluoroethyl, heptafluoroisopropyl, OCH3, tert-butoxy, OCHF2, OCF3, 2,2,2-trifluoroethoxy, heptafluoroisopropoxy, SCH3, SCH2CH3, SCHF2, SCF3, 2,2,2-trifluoroethylthio, heptafluoroisopropylthio, trifluoromethanesulfinyl, trifluoromethanesulfonyl, trifluoroethanesulfinyl or trifluoroethanesulfonyl.

[0069] In some embodiments of the present invention, preferably, in formula (I), R is selected from methyl, ethyl, chloroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl or phenyl.

[0070] In some embodiments of the present invention, preferably, Y 1 、Y 2 、Y 3 、Y 4 Each independently selected from H, halogen, CN, NO2, CH3, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, cyclopropyl, CF3, CHF2, 2,2,2-trifluoroethyl, heptafluoroisopropyl, OCH3, tert-butoxy, OCHF2, OCF3, 2,2,2-trifluoroethoxy, heptafluoroisopropoxy, SCH3, SCH2CH3, SCHF2, SCF3, 2,2,2-trifluoroethylthio, heptafluoroisopropylthio, trifluoromethanesulfinyl, trifluoromethanesulfonyl, trifluoroethanesulfinyl or trifluoroethanesulfonyl.

[0071] In some embodiments of the present invention, preferably, the compound of the structure shown in Formula I is selected from any of the following structures: Preferably

[0072] In some embodiments of the present invention, preferably, in the compound of the structure shown in Formula I, Q is selected from the following aromatic rings: Preferably

[0073] In some embodiments of the present invention, preferably, R 1 、R 2 、R 3 and R 4 Each is independently selected from H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkylsulfinyl, substituted or unsubstituted C1-C6 alkylsulfonyl or substituted or unsubstituted phenyl; wherein the substituted substituents are each independently selected from at least one of halogen, CN, NO2, formyl, C1-C3 alkyl or halogenated C1-C3 alkyl.

[0074] In some embodiments of the present invention, preferably, R 1 、R 2 、R 3 and R 4 Each is independently selected from H, C1-C6 alkyl, halogenated C1-C6 alkyl, substituted or unsubstituted C1-C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, phenyl or halogenated phenyl.

[0075] In some embodiments of the present invention, preferably, R 1 、R 2 、R 3 and R 4 Each is independently selected from H, CH3, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, CF3, 2,2,2-trifluoroethyl, heptafluoroisopropyl, trifluoromethanesulfinyl, trifluoromethanesulfonyl, phenyl, trifluoroethanesulfinyl or trifluoroethanesulfonyl.

[0076] In some embodiments of the present invention, preferably, the compound of formula I has the structure shown in formula IA.

[0077] wherein R is selected from methyl, ethyl, chloroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, allyl, propargyl, trifluoromethyl or phenyl;

[0078] Y 2 、Y 3 、Y 4 Each independently selected from H, halogen, CN, NO2, CH3, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, cyclopropyl, CF3, CHF2, 2,2,2-trifluoroethyl, heptafluoroisopropyl, OCH3, tert-butoxy, OCHF2, OCF3, 2,2,2-trifluoroethoxy, heptafluoroisopropoxy, SCH3, SCH2CH3, SCHF2, SCF3, 2,2,2-trifluoroethylthio, heptafluoroisopropylthio, trifluoromethanesulfinyl, trifluoromethanesulfonyl, trifluoroethanesulfinyl or trifluoroethanesulfonyl;

[0079] T 1 、T 2 、T 3 、T 4 、T 5 Each is independently selected from H, halogen, CN, NO2, CH3, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, cyclopropyl, CF3, CHF2, 2,2,2-trifluoroethyl, heptafluoroisopropyl, OCH3, tert-butoxy, OCHF2, OCF3, 2,2,2-trifluoroethoxy, heptafluoroisopropoxy, SCH3, SCH2CH3, SCHF2, SCF3, 2,2,2-trifluoroethylthio, heptafluoroisopropylthio, trifluoromethanesulfinyl, trifluoromethanesulfonyl, trifluoroethanesulfinyl or trifluoroethanesulfonyl.

[0080] Among the aromatic heterocyclic compounds of the present invention, there may be E- and Z-type geometric isomers depending on the types of substituents. The present invention includes these E- and Z-types, or mixtures containing these E- and Z-types in any ratio. In addition, among the compounds of the present invention, there may be optical isomers caused by having one or more asymmetric carbon atoms or asymmetric sulfur atoms. The present invention includes all optical isomers, racemates, and diastereomers.

[0081] In some embodiments, the compound of formula I is selected from at least one of the compounds shown in Tables 1-25.

[0082] The following expressions in the tables of this specification represent the following groups, respectively.

[0083] Me:methyl

[0084] Et: ethyl

[0085] t-Bu: tert-butyl

[0086] CF3: trifluoromethyl

[0087] OCF3: trifluoromethoxy

[0088] Ac:Acetyl

[0089] n-Pr: n-propyl

[0090] i-pr: isopropyl

[0091] n-Bu: n-butyl

[0092] i-Bu: isobutyl

[0093] s-Bu: sec-butyl

[0094] i-Am: isopentyl

[0095] Ph: phenyl

[0096] Table 1:

[0097] Q is selected from Q1, Z 1 Selected from CT 1 , Z 2 Selected from CT 2 , Z 3 Selected from CT 3 , Z 4 Selected from CT 4 , Z 5 Selected from CT 5 :

[0098] Table 2:

[0099] Q is selected from Q1, Z 1 Selected from CH, Z 2 Selected from N, Z 3 Selected from CT 3 , Z 4 Selected from CT 4 , Z 5 Selected from CH:

[0100] Table 3:

[0101] Q is selected from Q1, Z 1 Selected from CH, Z 2 Selected from CT 2 , Z 3 Selected from N, Z 4 Selected from CT 4 , Z 5 Selected from CH:

[0102] Table 4:

[0103] Q is selected from Q1, Z 1 Selected from N, Z 2 Selected from CT 2 , Z 3 Selected from CH, Z 4 Selected from CT 4 , Z 5 Selected from CH:

[0104] Table 5: Q is selected from Q2, Z 1 Selected from CT 1 , Z 2 Selected from CT 2 , Z 3 Selected from N, Z 4 Selected from CT 4 ;

[0105] Table 6: Q is selected from Q3, Z 1 Selected from CT 1 , Z 2 Selected from CT 2 , Z 3 Selected from CT 3 , Z 4 Selected from N;

[0106] Table 7: Q is selected from Q3, Z 1 Selected from CT 1 , Z2 Selected from N, Z 3 Selected from CT 3 , Z 4 Selected from N;

[0107] Table 8: Q is selected from Q3, Z 1 Selected from CT 1 , Z 2 Selected from CT 2 , Z 3 Selected from N, Z 4 Selected from N;

[0108] Table 9: Q is selected from Q3, Z 1 Selected from N, Z 2 Selected from CT 2 , Z 3 Selected from CT 3 , Z 4 Selected from N;

[0109] Table 10: Q is selected from Q3, Z 1 Selected from N, Z 2 Selected from CT 2 , Z 3 Selected from N, Z 4 Selected from N;

[0110] Table 11: Q is selected from Q3, Z 1 Selected from CT 1 , Z 2 Selected from CT 2 , Z 3 Selected from CT 3 , Z 4 Selected from CT 4 ;

[0111] Table 12: Q is selected from Q2, Z 1 Selected from O, Z 2 Selected from CT 2 , Z 3 Selected from CT 3 , Z 4 Selected from CT 4 ;

[0112] Table 13: Q is selected from Q2, Z 1 Selected from S, Z 2 Selected from CT 2 , Z 3 Selected from CT 3 , Z 4 Selected from CT 4 ;

[0113] Table 14: Q is selected from Q2, Z 1 Selected from CT 1 , Z 2 Selected from O, Z 3 Selected from CT 3 , Z 4 Selected from CT 4 ;

[0114] Table 15: Q is selected from Q2, Z 1 Selected from CT 1 , Z 2 Selected from S, Z 3 Selected from CT 3 , Z 4 Selected from CT 4 ;

[0115] Table 16: Q is selected from Q2, Z 1 Selected from S, Z 2 Selected from CT 2 , Z 3 Selected from N, Z 4 Selected from CT 4 ;

[0116] Table 17: Q is selected from Q2, Z 1 Selected from O, Z 2 Selected from CT 2 , Z 3 Selected from N, Z 4 Selected from CT 4 ;

[0117] Table 18: Q is selected from Q2, Z 1 Selected from CT 1 , Z 2 Selected from S, Z 3 Selected from CT 3 , Z 4 Selected from N;

[0118] Table 19: Q is selected from Q2, Z 1 Selected from CT 1 , Z 2 Selected from O, Z 3 Selected from CT 3 , Z 4 Selected from N;

[0119] Table 20: Q is selected from Q2, Z 1 Selected from N, Z 2 Selected from CT 2 , Z 3 Selected from CT 3 , Z 4 Selected from S;

[0120] Table 21: Q is selected from Q2, Z 1 Selected from N, Z 2 Selected from CT 2 , Z 3 Selected from CT 3 , Z 4 Selected from O;

[0121] Table 22: Q is selected from Q2, Z 1 Selected from O, Z 2 Selected from N, Z 3 Selected from CT 3 , Z 4 Selected from CT 4 ;

[0122] Table 23: Q is selected from Q2, Z 1 Selected from O, Z2 Selected from N, Z 3 Selected from CT 3 , Z 4 Selected from CT 4 ;

[0123] Table 24: Q is selected from Q2, Z 1 Selected from CT 1 , Z 2 Selected from CT 2 , Z 3 Selected from O, Z 4 Selected from N;

[0124] Table 25: Q is selected from Q2, Z 1 Selected from CT 1 , Z 2 Selected from CT 2 , Z 3 Selected from NR 3 , Z 4 Selected from N;

[0125] In some exemplary embodiments, the present invention provides the following compounds:

[0126] In some embodiments of the present invention, preferably, the salts in the aromatic heterocyclic compounds and / or their salts include but are not limited to inorganic salts such as hydrochlorides, sulfates, nitrates, phosphates; and organic salts such as acetates, fumarates, maleates, oxalates, methanesulfonates, benzenesulfonates, and p-toluenesulfonates.

[0127] In some embodiments of the present invention, preferably, a pyridoimidazole compound and / or a salt thereof is provided, wherein the pyridoimidazole compound has a structure shown in formula (I'):

[0128] Wherein, in formula (I'),

[0129] R is selected from substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10Alkynyl, and the optional substituents are each independently selected from halogen, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 at least one of cycloalkoxy groups;

[0130] Y1, Y2, Y3, Y4, and Y5 are each independently selected from H, halogen, CN, NO2, formyl, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Alkylthio, substituted or unsubstituted C1-C 10 Alkylsulfinyl, substituted or unsubstituted C1-C 10 Alkylsulfonyl, substituted or unsubstituted C1-C 10 Alkylcarbonyl, substituted or unsubstituted C1-C 10 Alkoxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C2-C6 alkenyloxy, substituted or unsubstituted C2-C6 alkynyloxy, substituted or unsubstituted C1-C 10 Alkylcarbonyloxy, substituted or unsubstituted C1-C 10 Cyanoalkyl, substituted or unsubstituted C1-C 10 substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryl C1-C6 alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C1-C6 alkoxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylthio, substituted or unsubstituted aryl C1-C6 alkylsulfonyl, substituted or unsubstituted aryl C1-C6 alkylsulfinyl, substituted or unsubstituted aryl C1-C6 alkylthio, substituted or unsubstituted heterocycle, substituted or unsubstituted heterocycle C1-C6 alkyl, substituted or unsubstituted heterocycleoxy, and each group of optionally present substituents is independently selected from halogen, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 At least one of cycloalkoxy; optionally, Y 1 、Y 2 、Y 3 、Y 4 、Y 5 Any two adjacent groups form a group, and at least one group is cyclized with the bonded benzene ring via or without at least one heteroatom to form at least one 3- to 8-membered ring;

[0131] Z1, Z2, Z3 are each independently selected from H, halogen, CN, NO2, formyl, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Alkylthio, substituted or unsubstituted C1-C 10 Alkylsulfinyl, substituted or unsubstituted C1-C 10 Alkylsulfonyl, substituted or unsubstituted C1-C 10 Alkylcarbonyl, substituted or unsubstituted C1-C 10 substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C2-C6 alkenyloxy, substituted or unsubstituted C2-C6 alkynyloxy, substituted or unsubstituted C1-C 10 Alkylcarbonyloxy, substituted or unsubstituted C1-C 10 Cyanoalkyl, substituted or unsubstituted C1-C 10 substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryl C1-C6 alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C1-C6 alkoxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylthio, substituted or unsubstituted aryl C1-C6 alkylsulfonyl, substituted or unsubstituted aryl C1-C6 alkylsulfinyl, substituted or unsubstituted aryl C1-C6 alkylthio, substituted or unsubstituted heterocycle, substituted or unsubstituted heterocycle C1-C6 alkyl, substituted or unsubstituted heterocycleoxy, and each group of optionally present substituents is independently selected from halogen, C1-C 10 Alkyl, halogenated C1-C10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 At least one of cycloalkoxy; optionally, any two adjacent groups of Z1, Z2, and Z3 form a group, and at least one group is cyclized with the bonded pyridine ring via or without at least one heteroatom to form at least one 3- to 8-membered ring;

[0132] According to the present invention, the term "optionally" means that a polycyclic ring structure may or may not exist.

[0133] According to the present invention, any two adjacent groups among Y1, Y2, Y3, Y4, and Y5 form a group, and at least one group forms at least one 3- to 8-membered ring with the bonded benzene ring via or without at least one heteroatom, which means that at least one combination of Y1 and Y2, Y2 and Y3, Y3 and Y4, or Y4 and Y5 forms at least one 3- to 8-membered ring with the bonded benzene ring via or without at least one heteroatom. 1 , Z 2 , Z 3 It has a similar definition and will not be repeated here.

[0134] In some embodiments of the present invention, preferably, in formula (I'),

[0135] R is selected from C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl substituted C1-C 10 Alkyl, halogenated C3-C 10 Cycloalkyl substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl substituted halogenated C1-C 10 Alkyl, C1-C 10 Alkoxy substituted C1-C 10 Alkyl, halogenated C1-C 10 Alkoxy substituted C1-C 10 Alkyl, C1-C 10 Alkoxy substituted halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkoxy substituted C1-C 10 Alkyl, halogenated C3-C 10 Cycloalkoxy substituted C1-C 10 Alkyl, C3-C 10 Cycloalkoxy substituted halogenated C1-C10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkyl substituted C3-C 10 Cycloalkyl, halogenated C1-C 10 Alkyl substituted C3-C 10 Cycloalkyl, C1-C 10 Alkyl substituted halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy substituted C3-C 10 Cycloalkyl, halogenated C1-C 10 Alkoxy substituted C3-C 10 Cycloalkyl, C1-C 10 Alkoxy substituted halogenated C3-C 10 Cycloalkyl, C3-C 10 Cycloalkoxy substituted C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkoxy substituted C3-C 10 Cycloalkyl, C3-C 10 Cycloalkoxy substituted halogenated C3-C 10 Cycloalkyl, C2-C 10 Alkenyl, halogenated C2-C 10 Alkenyl, C2-C 10 Alkynyl, halogenated C2-C 10 Alkynyl;

[0136] Y1, Y2, Y3, Y4, Y5 are each independently selected from H, halogen, CN, NO2, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl substituted C1-C 10 Alkyl, halogenated C3-C 10 Cycloalkyl substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl substituted halogenated C1-C 10 Alkyl, C1-C 10 Alkoxy substituted C1-C 10 Alkyl, halogenated C1-C 10 Alkoxy substituted C1-C 10 Alkyl, C1-C 10 Alkoxy substituted halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkyl substituted C3-C 10 Cycloalkyl, halogenated C1-C10 Alkyl substituted C3-C 10 Cycloalkyl, C1-C 10 Alkyl substituted halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C1-C 10 Alkylthio, halogenated C1-C 10 Alkylthio, C1-C 10 Alkylsulfinyl, halogenated C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, halogenated C1-C 10 Alkylsulfonyl, formyl, C1-C 10 Alkylcarbonyl, halogenated C1-C 10 Alkylcarbonyl, C1-C 10 Alkoxycarbonyl, halogenated C1-C 10 Alkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, halogenated C2-C6 alkenyloxy, halogenated C2-C6 alkynyloxy, C1-C 10 Alkylcarbonyloxy, halogenated C1-C 10 Alkylcarbonyloxy, C1-C 10 Cyanoalkyl, C1-C 10 Cyanoalkoxy, C1-C 10 Alkyl-substituted silyl, substituted or unsubstituted amino, aryl, aryl C1-C6 alkyl, aryloxy, aryl C1-C6 alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C1-C6 alkylsulfonyl, aryl C1-C6 alkylsulfinyl, aryl C1-C6 alkylthio, heterocycle, heterocycle C1-C6 alkyl, heterocycleoxy, and each group of substituents that are optionally present are independently selected from halogen, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 At least one of cycloalkoxy groups; optionally, any two adjacent groups of Y1, Y2, Y3, Y4, and Y5 form a group, and at least one group is cyclized with the bonded benzene ring via or without at least one heteroatom to form at least one 3- to 8-membered ring;

[0137] Z1, Z2, Z3 are each independently selected from H, halogen, CN, NO2, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl substituted C1-C 10 Alkyl, halogenated C3-C 10 Cycloalkyl substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl substituted halogenated C1-C 10 Alkyl, C1-C 10 Alkoxy substituted C1-C 10 Alkyl, halogenated C1-C 10 Alkoxy substituted C1-C 10 Alkyl, C1-C 10 Alkoxy substituted halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkyl substituted C3-C 10 Cycloalkyl, halogenated C1-C 10 Alkyl substituted C3-C 10 Cycloalkyl, C1-C 10 Alkyl substituted halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C1-C 10 Alkylthio, halogenated C1-C 10 Alkylthio, C1-C 10 Alkylsulfinyl, halogenated C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, halogenated C1-C 10 Alkylsulfonyl, formyl, C1-C 10 Alkylcarbonyl, halogenated C1-C10 alkylcarbonyl, C1-C 10 Alkoxycarbonyl, halogenated C1-C10 alkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, halogenated C2-C6 alkenyloxy, halogenated C2-C6 alkynyloxy, C1-C 10 Alkylcarbonyloxy, halogenated C1-C 10 Alkylcarbonyloxy, C1-C 10 Cyanoalkyl, C1-C 10 Cyanoalkoxy, C1-C 10Alkyl-substituted silyl, substituted or unsubstituted amino, aryl, aryl C1-C6 alkyl, aryloxy, aryl C1-C6 alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C1-C6 alkylsulfonyl, aryl C1-C6 alkylsulfinyl, aryl C1-C6 alkylthio, heterocycle, heterocycle C1-C6 alkyl, heterocycleoxy, and each group of substituents that are optionally present are independently selected from halogen, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 At least one of cycloalkoxy groups; optionally, any two adjacent groups among Z1, Z2, and Z3 form a group, and at least one group is cyclized with the bonded pyridine ring via or without at least one heteroatom to form at least one 3- to 8-membered ring.

[0138] Several particularly preferred embodiments of the pyridoimidazole compounds of the present invention are provided below.

[0139] Specific implementation method 1

[0140] R is selected from C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl substituted C1-C8 alkyl, halogenated C3-C8 cycloalkyl substituted C1-C8 alkyl, C3-C8 cycloalkyl substituted halogenated C1-C8 alkyl, C1-C8 alkoxy substituted C1-C8 alkyl, halogenated C1-C8 alkoxy substituted C1-C8 alkyl, C1-C8 alkoxy substituted halogenated C1-C8 alkyl, C3-C8 cycloalkyloxy substituted C1-C8 alkyl, halogenated C3-C8 cycloalkyloxy substituted C1-C8 alkyl, C3-C8 cycloalkyloxy substituted halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, halogenated C1-C8 alkyl-substituted C3-C8 cycloalkyl, C1-C8 alkyl-substituted halogenated C3-C8 cycloalkyl, C1-C8 alkoxy-substituted C3-C8 cycloalkyl, halogenated C1-C8 alkoxy-substituted C3-C8 cycloalkyl, C1-C8 alkoxy-substituted halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyloxy-substituted C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyloxy-substituted C3-C8 cycloalkyl, C3-C8 cycloalkyloxy-substituted halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl;

[0141] Y1, Y2, Y3, Y4, and Y5 are each independently selected from H, halogen, CN, NO2, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl substituted C1-C8 alkyl, halogenated C3-C8 cycloalkyl substituted C1-C8 alkyl, C3-C8 cycloalkyl substituted halogenated C1-C8 alkyl, C1-C8 alkoxy substituted C1-C8 alkyl, halogenated C1-C8 alkoxy substituted C1-C8 alkyl, C1-C8 alkoxy substituted halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, halogenated C1-C8 alkyl-substituted C3-C8 cycloalkyl, C1-C8 alkyl-substituted halogenated C3-C8 cycloalkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkylthio, halogenated C1-C8 alkylthio, C1-C8 alkylsulfinyl, halogenated C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, halogenated C1-C8 alkylsulfonyl;

[0142] Z1, Z2, and Z3 are each independently selected from H, halogen, CN, NO2, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkylthio, halogenated C1-C8 alkylthio, C1-C8 alkylsulfinyl, halogenated C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, and halogenated C1-C8 alkylsulfonyl;

[0143] Specific embodiment 2

[0144] In formula (I'),

[0145] R is selected from C1-C8 alkyl, halo-substituted C1-C8 alkyl, C3-C8 cycloalkyl, halo-substituted C3-C8 cycloalkyl, C2-C8 alkenyl, halo-substituted C2-C8 alkenyl, C2-C8 alkynyl and halo-substituted C2-C8 alkynyl;

[0146] Y1, Y2, Y3, Y4, and Y5 are each independently selected from H, halogen, CN, NO2, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkylthio, halogenated C1-C8 alkylthio, C1-C8 alkylsulfinyl, halogenated C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, and halogenated C1-C8 alkylsulfonyl;

[0147] Z1, Z2, and Z3 are each independently selected from H, halogen, CN, NO2, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkylthio, halogenated C1-C8 alkylthio, C1-C8 alkylsulfinyl, halogenated C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, and halogenated C1-C8 alkylsulfonyl;

[0148] Specific embodiment 3

[0149] In formula (I'),

[0150] R is selected from C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C5 alkenyl, C2-C5 alkynyl;

[0151] Y1, Y2, Y3, Y4, and Y5 are each independently selected from H, halogen, CN, NO2, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, and halogenated C1-C8 alkoxy;

[0152] Z1, Z2, and Z3 are each independently selected from H, halogen, CN, NO2, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, and halogenated C1-C8 alkoxy;

[0153] Specific implementation method 4

[0154] In formula (I'),

[0155] R is selected from methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, allyl, propargyl, CF3;

[0156] Y1, Y2, Y3, Y4, and Y5 are each independently selected from H, F, Cl, Br, I, CN, NO2, CH3, tert-butyl, CF3, OCH3, OCF3, OCH2CF3, OCH2CF2CF3, CF2Cl, CFCl2, and CCl3;

[0157] Z1, Z2, and Z3 are each independently selected from H, F, Cl, Br, I, CN, NO2, CH3, CF3, OCF3, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl;

[0158] Specific implementation method 5

[0159] In formula (I'),

[0160] R is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl;

[0161] Y1, Y2, Y3, Y4, and Y5 are each independently selected from H, F, Cl, Br, CN, NO2, OCF3, CH3, CF3, OCH3, OCH2CF3, and OCH2CF2CF3;

[0162] Z1, Z2, Z3 are each independently selected from H, F, Cl, Br, CH3, tert-butyl;

[0163] Specific embodiment 6

[0164] In formula (I'),

[0165] R is selected from ethyl and n-propyl;

[0166] Y1, Y2, Y3, Y4, and Y5 are each independently selected from H, F, Cl, Br, CN, NO2, OCF3, CH3, tert-butyl, CF3, and OCH3;

[0167] Z1, Z2, Z3 are each independently selected from H, Cl, CH3;

[0168] Specific embodiment 7

[0169] The pyridoimidazole compound is selected from at least one of the compounds shown in Table 26:

[0170] Table 26

[0171] Specific embodiment 8

[0172] The pyridimidazole compound is selected from at least one of compounds I-2, I-29, I-30, I-39, I-43, and I-50, and the compounds have the chemical structures shown in formula (I-2), formula (I-57), formula (I-30), formula (I-50), formula (I-39), formula (I-43), and formula (I-29), respectively.

[0173] Specific embodiment 9

[0174] The pyridimidazole compound is selected from at least one of compounds I-2, I-29, I-30, I-39, I-43, and I-50, and the compounds have the chemical structures shown in formula (I-2), formula (I-30), formula (I-50), formula (I-39), formula (I-43), and formula (I-29), respectively.

[0175] Specific embodiment mode 10

[0176] The pyridimidazole-containing compound is selected from at least one of compounds I-2, I-29, I-30, I-39, I-43, and I-50.

[0177] The inventors of the present invention have found that the pyridoimidazole compounds or salts thereof in the several preferred embodiments provided above have better insecticidal and acaricidal effects, especially the pyridine-containing benzimidazole compounds or salts thereof in preferred embodiments I-2, I-29, I-30, I-39, I-43, and I-50, and especially the compounds in preferred embodiments I-2, I-29, I-30, I-39, I-43, and I-50 have better insecticidal and acaricidal effects. When used at low concentrations (e.g., 0.78 mg / L), they can exhibit excellent insecticidal and acaricidal effects.

[0178] In some embodiments of the present invention, preferably, the salts in the pyridimidazole compounds and / or their salts include but are not limited to inorganic salts such as hydrochlorides, sulfates, nitrates, phosphates; and organic salts such as acetates, fumarates, maleates, oxalates, methanesulfonates, benzenesulfonates, and p-toluenesulfonates.

[0179] The present invention has no particular requirements for the specific preparation method of the compound described in the first aspect. A person skilled in the art can determine a suitable synthesis method based on the structural formula provided by the present invention in combination with known knowledge in the field of organic synthesis, or a person skilled in the art can also prepare the aforementioned compound based on the specific examples provided below by the present invention (substitution of raw materials). However, preferably, the second aspect of the present invention provides a method for preparing an aromatic heterocyclic compound and / or its salt, the method comprising:

[0180] (1) in a first solvent, in the presence of a first alkaline substance and a condensing agent, subjecting compound V and compound IV to a condensation reaction to obtain compound III;

[0181] (2) in a second solvent, subjecting the compound III to a cyclization reaction with an acidic substance to obtain a compound II;

[0182] (3) in a third solvent, in the presence of a second alkaline substance, subjecting the compound II to a sulfonylation reaction with a sulfonyl-containing compound to obtain compound I;

[0183] Wherein, the compound V has a structure represented by formula (V), the compound IV has a structure represented by formula (IV), the compound III has a structure represented by formula (III), the compound II has a structure represented by formula (II), the compound I has a structure represented by formula (I), and the sulfonyl-containing compound has a structure represented by formula (VI);

[0184] In formula (I), formula (II), formula (III), formula (IV), formula (V) and formula (VI), R, X 1 、X 2 、X 3 、X 4 , Q has the same definition as described in the first aspect of the present invention, and L is selected from halogen.

[0185] In some embodiments of the present invention, preferably, in step (1), the conditions of the condensation reaction include: temperature of -10°C to 150°C, and reaction time of 0.5-48h.

[0186] In some embodiments of the present invention, preferably, in step (1), the molar ratio of the compound V to the compound IV is 0.5-2: 1. The compound V and the compound IV can be obtained commercially.

[0187] In some embodiments of the present invention, preferably, in step (1), the condensing agent is selected from at least one of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or its hydrochloride (EDCI), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), diethyl cyanophosphate (DEPC), chlorocarbonate compounds, and 2-chloro-1-methylpyridinium iodide.

[0188] In some embodiments of the present invention, preferably, in step (1), the molar ratio of the condensing agent to the compound IV is 1-2:1.

[0189] In some embodiments of the present invention, preferably, in step (1), the first alkaline substance is selected from at least one of pyridine, dimethylaminopyridine (DMAP), triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene.

[0190] In some embodiments of the present invention, preferably, in step (1), the molar ratio of the first alkaline substance to the compound IV is 0.1-10:1.

[0191] In some embodiments of the present invention, preferably, in step (1), the first solvent is selected from at least one of pyridine, dichloromethane, chloroform, carbon tetrachloride benzene, toluene, xylene, chlorobenzene, dichlorobenzene, ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA), N-methylpyrrolidone (NMP), acetone, methyl ethyl ketone, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone.

[0192] In some embodiments of the present invention, preferably, in step (1), the amount of the first solvent used is 1-20 mL relative to 1 mmol of the compound IV.

[0193] According to the present invention, in step (1), the first solvent and the first alkaline substance may be the same, for example, pyridine. In addition, it should be noted that when the first solvent and the first alkaline substance are the same substance, they need to be measured separately.

[0194] In some embodiments of the present invention, preferably, in step (2), the conditions of the cyclization reaction include: a temperature of -10°C to 300°C, and a reaction time of 0.5-48h.

[0195] In some embodiments of the present invention, preferably, in step (2), the acidic substance is selected from at least one of p-toluenesulfonic acid or a hydrate thereof, methanesulfonic acid, trifluoromethanesulfonic acid, hydrochloric acid, sulfuric acid, nitric acid, formic acid, acetic acid, propionic acid, trifluoroacetic acid, trichloroacetic acid, benzoic acid, and phosphoric acid. The p-toluenesulfonic acid hydrate is preferably p-toluenesulfonic acid monohydrate.

[0196] In some embodiments of the present invention, preferably, in step (2), the molar ratio of the acidic substance to the compound III is 0.01-10:1.

[0197] In some embodiments of the present invention, preferably, in step (2), the second solvent is selected from at least one of acetic acid, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA), N-methylpyrrolidone (NMP), ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, benzene, toluene, xylene, acetone, methyl ethyl ketone, dichloromethane, chloroform, carbon tetrachloride, chlorobenzene, dichlorobenzene, ethyl acetate, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone.

[0198] In some embodiments of the present invention, preferably, in step (2), the amount of the second solvent used is 1-20 mL relative to 1 mmol of the compound III.

[0199] In some embodiments of the present invention, preferably, step (2) further comprises: adjusting the pH value of the system to 7-10 using an alkaline solution after the cyclization reaction, wherein the alkaline solution is, for example, an aqueous sodium hydroxide solution.

[0200] In some embodiments of the present invention, preferably, in step (3), the conditions of the sulfonylation reaction include: a temperature of -10°C to 100°C, and a reaction time of 0.5-48h.

[0201] In some embodiments of the present invention, preferably, in step (3), the molar ratio of ethylsulfonyl chloride to the compound II is 0.8-10:1.

[0202] In some embodiments of the present invention, preferably, in step (3), the second alkaline substance is selected from at least one of pyridine, dimethylaminopyridine (DMAP), triethylamine, diisopropylethylamine, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene.

[0203] In some embodiments of the present invention, preferably, in step (3), the molar ratio of the second alkaline substance to the compound II is 1-10:1.

[0204] In some embodiments of the present invention, preferably, in step (3), the third solvent is selected from at least one of diethyl ether, tetrahydrofuran (THF), 2-methyltetrahydrofuran, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA), N-methylpyrrolidone (NMP), dioxane, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, chlorobenzene, and dichlorobenzene.

[0205] In some embodiments of the present invention, preferably, in step (3), the amount of the third solvent used is 1-20 mL relative to 1 mmol of the compound II.

[0206] In some embodiments of the present invention, preferably, step (3) comprises: in a third solvent, in the presence of a second alkaline substance, first subjecting the compound II to a first stage of sulfonylation reaction, and then adding the ethylsulfonyl chloride to carry out a second stage of sulfonylation reaction to obtain the pyridimidazole compound.

[0207] In some embodiments of the present invention, preferably, the conditions of the first stage of the sulfonylation reaction include: a temperature of -10°C to 100°C, and a reaction time of 10-120 min.

[0208] In some embodiments of the present invention, preferably, the conditions of the second stage of the sulfonylation reaction include: temperature of -10°C to 100°C, and reaction time of 0.5-48h.

[0209] According to the present invention, the method may also include various post-processing operation means currently used in the art, such as extraction, washing, drying, filtration, concentration, separation and purification. The present invention is not particularly limited to this, and various conventional operations in the art can be used for the method, such as extraction using ethyl acetate; drying using anhydrous sodium sulfate; concentration using reduced pressure concentration; separation and purification using column chromatography separation and purification, etc.

[0210] The present invention also provides another method for preparing the compound represented by formula I, characterized in that the method comprises:

[0211] (a) condensing compound X and compound VI in the presence of a fourth solvent and a third basic substance;

[0212] (b) subjecting the product compound IX of the condensation reaction in step (a) to a reduction reaction with a reducing substance in the presence of a fifth solvent;

[0213] (c) condensing the product of the reduction reaction in step (b), compound VIII, and compound XI in the presence of a sixth solvent;

[0214] (d) subjecting the product of the condensation reaction, Compound VII, to an addition ring-closure reaction in the presence of a seventh solvent;

[0215] Wherein, the compound I has the structure shown in formula (I), the compound VII has the structure shown in formula (VII), the compound VIII has the structure shown in formula (VIII), the compound IX has the structure shown in formula (IX), the compound X has the structure shown in formula (X), the compound XI has the structure shown in formula (XI), and the compound VI has the structure shown in formula (VI);

[0216] Among them, R, X 1 、X 2 、X 3 、X 4 The definitions of Q are the same as those described in the first aspect of the present invention, and L is selected from halogen.

[0217] In some embodiments of the present invention, preferably, the third alkaline substance is selected from at least one of pyridine, dimethylaminopyridine, triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide and 1,8-diazabicyclo[5.4.0]undec-7-ene.

[0218] In some embodiments of the present invention, preferably, the molar ratio of the compound X to the compound VI is 0.5-2:1;

[0219] In some embodiments of the present invention, preferably, in step (a), the conditions of the condensation reaction include: a temperature of -20°C to 150°C, and a reaction time of 0.1-48h;

[0220] In some embodiments of the present invention, preferably, the reducing substance is selected from at least one of hydrogen, metal, sulfide, borane and its complex and hydrosulfite.

[0221] In some embodiments of the present invention, preferably, in step (b), the reduction reaction conditions include: temperature of -10°C to 200°C, and reaction time of 0.5-72h.

[0222] In some embodiments of the present invention, preferably, the molar ratio of the compound VIII to the compound XI is 0.5-2:1.

[0223] In the present invention, the reaction in step (c) can be carried out in the presence of a first catalyst.

[0224] In some embodiments of the present invention, preferably, the first catalyst is selected from at least one of glacial acetic acid, propionic acid, amino acid and Lewis acid.

[0225] In some embodiments of the present invention, preferably, in step (c), the conditions of the condensation reaction include: a temperature of -20°C to 150°C, and a reaction time of 0.1-48h;

[0226] In some embodiments of the present invention, preferably, the reaction in step (d) can be carried out in the presence of a second catalyst.

[0227] In some embodiments of the present invention, preferably, the second catalyst is selected from iodide, bromide, glacial acetic acid, propionic acid, amino acid, and Lewis acid.

[0228] In some embodiments of the present invention, preferably, the fourth to seventh solvents are each independently selected from at least one of methanol, ethanol, isopropanol, propanol, butanol, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, ethyl acetate, toluene, xylene, acetonitrile, tetrahydrofuran, acetone, N,N-dimethylformamide, N-methylpyrrolidone, dioxane and water.

[0229] In some embodiments of the present invention, preferably, in step (d), the condensation reaction conditions include: temperature of -20°C to 150°C, and reaction time of 0.1-48h.

[0230] In some embodiments of the present invention, preferably, the method for preparing a pyridoimidazole compound and / or a salt thereof comprises:

[0231] (1) in a first solvent, in the presence of a first alkaline substance and a condensing agent, subjecting compound V' and compound IV' to a condensation reaction to obtain compound III';

[0232] (2) in a second solvent, subjecting the compound III' to a cyclization reaction with an acidic substance to obtain compound II';

[0233] (3) in a third solvent, in the presence of a second alkaline substance, subjecting the compound II' to a sulfonylation reaction with a sulfonyl group-containing compound to obtain the pyridimidazole compound;

[0234] Wherein, the compound V' has a structure shown in formula (V'), the compound IV has a structure shown in formula (IV'), the compound III has a structure shown in formula (III'), the compound II has a structure shown in formula (II'), the pyridimidazole-containing compound has a structure shown in formula (I'), and the ethylsulfonyl compound has a structure shown in formula (VI');

[0235] In formula (I'), formula (II'), formula (III'), formula (IV'), formula (V') and formula (VI'), the definitions of R, Y1, Y2, Y3, Y4, Y5, Z1, Z2, and Z3 are the same as those described in the first aspect above, and X is selected from halogen.

[0236] In the method for preparing the pyridimidazole compound and / or its salt, the definitions of the first to third solvents, the first alkaline substance, the second alkaline substance, the condensing agent and the acidic substance are the same as those described below.

[0237] As mentioned above, the third aspect of the present invention provides the use of at least one of the aromatic heterocyclic compounds and / or salts thereof, pyridimidazole compounds or salts thereof described in the first aspect of the present invention in the preparation of insecticides and acaricides and / or parasite control agents.

[0238] Preferably, at least one of the aromatic heterocyclic compounds and / or salts thereof, and the pyridoimidazole compounds or salts thereof is used as an active ingredient (ie, effective ingredient) in the insecticide and acaricide and / or parasite control agent.

[0239] In some embodiments of the present invention, preferably, the insects are selected from the group consisting of diamondback moth, beet armyworm, corn borer, striped stem borer, armyworm, thrips, and flea beetles; and the mites are selected from the group consisting of spider mites, two-spotted spider mites, citrus mites, and tea yellow mites.

[0240] As mentioned above, the fourth aspect of the present invention provides an insecticide and acaricide, which contains an active ingredient, and the active ingredient is selected from at least one of the aromatic heterocyclic compounds and / or their salts, pyridimidazole compounds and / or their salts described in the first aspect of the present invention.

[0241] In some embodiments of the present invention, preferably, the active ingredient is present in an amount of 1-99% by weight, based on the total weight of the insecticide and acaricide. For example, the active ingredient is present in an amount of 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 99%, or any value in a range formed by any two of these values. More preferably, the active ingredient is present in an amount of 5-60% by weight, based on the total weight of the insecticide and acaricide.

[0242] In some embodiments of the present invention, the insecticide and acaricide preferably further comprises a carrier. Preferably, the carrier in the insecticide and acaricide is a substance acceptable in agriculture, forestry, and horticulture and facilitates the application of the active ingredient. Particularly preferably, the carrier is a liquid carrier and / or a solid carrier, wherein the solid carrier is preferably selected from at least one solid substance selected from clay, natural or synthetic silicates, silicon dioxide, resins, waxes, and solid fertilizers; and the liquid carrier is preferably selected from water, alcohols, ketones, petroleum fractions, aromatic hydrocarbons, chlorinated hydrocarbons, and liquefied gas.

[0243] In some embodiments of the present invention, preferably, the insecticide and acaricide may further contain surfactants, protective colloids, adhesives, thickeners, thixotropic agents, penetrants, chelating agents, colorants, polymers and other commonly used auxiliary components in the art. The present invention is not particularly limited thereto, and those skilled in the art may select a reasonable composition and dosage according to actual needs.

[0244] In some embodiments of the present invention, preferably, the formulations of the insecticide and acaricide are each independently selected from at least one of wettable powders, soluble powders, emulsifiable concentrates, aqueous suspensions, dispersible oil suspensions, aqueous emulsions, suspoemulsions, microemulsions, aqueous solutions, granules, microcapsules, and water-dispersible granules. As a result, the active ingredient is more easily dissolved or dispersed, making it easier to disperse when used as an active substance of an insecticide or acaricide, thereby improving the application effect.

[0245] In some embodiments of the present invention, preferably, the present invention has no particular limitation on the preparation method of the insecticide and acaricide, and those skilled in the art may refer to the methods in existing literature and standards in the field or adopt existing methods in the field to prepare the agent to obtain the desired composition and dosage form.

[0246] As mentioned above, the fifth aspect of the present invention provides the use of the insecticide and acaricide according to the fourth aspect of the present invention in killing insects and / or acaricides in agriculture, forestry and horticulture.

[0247] The present invention will be described in detail below through examples.

[0248] In the following examples, unless otherwise specified, all raw materials used are commercially available.

[0249] In the following examples, unless otherwise specified, room temperature refers to 25±2°C.

[0250] Example 1

[0251] This example is the preparation of compound I-2

[0252] The specific preparation process is as follows:

[0253] (1) Add the first solvent (pyridine, 15 mL) to the reaction flask, add the condensing agent (EDCI, 12 mmol) and the first alkaline substance (DMAP, 1.6 mmol), add compound IV'-2 and compound V'-2 (3,5-bis(trifluoromethylbenzoic acid)) (8 mmol) and react at room temperature for 3 hours to carry out the first reaction, then add water, extract with ethyl acetate, wash the organic phase with saturated brine, and dry over anhydrous sodium sulfate. Filter and concentrate the filtrate under reduced pressure to obtain compound III-2;

[0254] (2) The obtained compound III'-2 was dissolved in a second solvent (glacial acetic acid, 20 mL) and refluxed at 117.9°C for 4 h for a second reaction. The mixture was cooled to room temperature, and the pH value of the system was adjusted to 9 by adding sodium hydroxide aqueous solution. The mixture was then extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain compound II' (II'-2, 6.4 mmol).

[0255] (3) Compound II-2 was dissolved in a third solvent (THF, 20 mL), and a second alkaline substance (0.76 g of mineral oil-coated NaH, NaH content 60 wt%, NaH 19 mmol) was added. After reacting at room temperature for 10 min, an ethylsulfonyl compound (ethylsulfonyl chloride, 19 mmol) was added and reacted at room temperature for 12 h. Saturated ammonium chloride was added to quench the reaction, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting product was separated and purified by column chromatography to obtain compound I-2 (2.71 g) as a white solid.

[0256] Example 2

[0257] This example is the preparation of compound I-57

[0258] The specific preparation process is as follows:

[0259] (1) Add the first solvent (pyridine, 15 mL) to the reaction flask, add the condensing agent (EDCI, 12 mmol) and the first alkaline substance (DMAP, 1.6 mmol), add compound IV'-57 and compound V'-2 (3,5-bis(trifluoromethylbenzoic acid)) (8 mmol) and react at room temperature for 3 hours to carry out the first reaction, then add water, extract with ethyl acetate, wash the organic phase with saturated brine, and dry over anhydrous sodium sulfate. Filter and concentrate the filtrate under reduced pressure to obtain compound III-57;

[0260] (2) The obtained compound III'-57 was dissolved in a second solvent (glacial acetic acid, 20 mL) and refluxed at 117.9°C for 4 h for a second reaction. The mixture was cooled to room temperature, and the pH value of the system was adjusted to 9 by adding sodium hydroxide aqueous solution. The mixture was then extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain compound II (II'-57, 6.3 mmol).

[0261] (3) Compound II'-57 was dissolved in a third solvent (THF, 20 mL), and a second alkaline substance (0.76 g of mineral oil-coated NaH, NaH content 60 wt%, NaH 19 mmol) was added. After reacting at room temperature for 10 min, an ethylsulfonyl compound (ethylsulfonyl chloride, 19 mmol) was added and reacted at room temperature for 12 h. Saturated ammonium chloride was added to quench the reaction, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting product was separated and purified by column chromatography to obtain compound I-57 (2.6 g) as a white solid.

[0262] Example 3

[0263] This example is the preparation of compound I-30

[0264] (1) Add the first solvent (pyridine, 15 mL) to the reaction flask, add the condensing agent (EDCI, 12 mmol) and the first alkaline substance (DMAP, 1.6 mmol), add compound IV'-30 and compound V'-2 (8 mmol) and react at room temperature for 3 hours to carry out the first reaction, then add water, extract with ethyl acetate, wash the organic phase with saturated brine, and dry over anhydrous sodium sulfate. Filter and concentrate the filtrate under reduced pressure to obtain compound III-30;

[0265] (2) The obtained compound III'-30 was dissolved in a second solvent (glacial acetic acid, 20 mL) and refluxed at 117.9°C for 4 h for a second reaction. The mixture was cooled to room temperature, and the pH value of the system was adjusted to 9 by adding sodium hydroxide aqueous solution. The mixture was then extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain compound II (II'-30, 6.6 mmol).

[0266] (3) Compound II'-30 was dissolved in a third solvent (THF, 20 mL), and a second alkaline substance (0.76 g of mineral oil-coated NaH, NaH content 60 wt%, NaH 19 mmol) was added. After reacting at room temperature for 10 min, an ethylsulfonyl compound (ethylsulfonyl chloride, 19 mmol) was added and reacted at room temperature for 12 h. Saturated ammonium chloride was added to quench the reaction, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting product was separated and purified by column chromatography to obtain compound I-30 (2.8 g) as a white solid.

[0267] Example 4

[0268] This example is the preparation of compound I-50

[0269] The specific preparation process is as follows:

[0270] (1) Add the first solvent (pyridine, 15 mL) to the reaction flask, add the condensing agent (EDCI, 12 mmol) and the first alkaline substance (DMAP, 1.6 mmol), add compound IV'-30 and compound V'-1 (3,5-di-tert-butylbenzoic acid) (8 mmol) and react at room temperature for 3 hours to perform the first reaction, then add water, extract with ethyl acetate, wash the organic phase with saturated brine, and dry over anhydrous sodium sulfate. Filter and concentrate the filtrate under reduced pressure to obtain compound III-50;

[0271] (2) The obtained compound III'-50 was dissolved in a second solvent (glacial acetic acid, 20 mL) and refluxed at 117.9°C for 4 h for a second reaction. The mixture was cooled to room temperature, and the pH value of the system was adjusted to 9 by adding sodium hydroxide aqueous solution. The mixture was then extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain compound II (II'-50, 6.2 mmol).

[0272] (3) Compound II'-50 was dissolved in a third solvent (THF, 20 mL), and a second alkaline substance (0.76 g of mineral oil-coated NaH, NaH content 60 wt%, NaH 19 mmol) was added. After reacting at room temperature for 10 min, an ethylsulfonyl compound (ethylsulfonyl chloride, 19 mmol) was added and reacted at room temperature for 12 h. Saturated ammonium chloride was added to quench the reaction, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting product was separated and purified by column chromatography to obtain compound I-50 (2.5 g) as a white solid.

[0273] Example 5

[0274] This example is the preparation of compound I-39

[0275] The specific preparation process is as follows:

[0276] (1) Add the first solvent (pyridine, 15 mL) to the reaction flask, add the condensing agent (EDCI, 12 mmol) and the first alkaline substance (DMAP, 1.6 mmol), add compound IV'-30 and compound V'-3 (3,5-dichlorobenzoic acid) (8 mmol) and react at room temperature for 3 hours to carry out the first reaction, then add water, extract with ethyl acetate, wash the organic phase with saturated brine, and dry over anhydrous sodium sulfate. Filter and concentrate the filtrate under reduced pressure to obtain compound III'-39;

[0277] (2) The obtained compound III'-39 was dissolved in a second solvent (glacial acetic acid, 20 mL) and refluxed at 117.9°C for 4 h for a second reaction. The mixture was cooled to room temperature, and the pH value of the system was adjusted to 9 by adding sodium hydroxide aqueous solution. The mixture was then extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain compound II (II'-39, 6.1 mmol).

[0278] (3) Compound II'-39 was dissolved in a third solvent (THF, 20 mL), and a second alkaline substance (0.76 g of mineral oil-coated NaH, NaH content 60 wt%, NaH 19 mmol) was added. After reacting at room temperature for 10 min, an ethylsulfonyl compound (ethylsulfonyl chloride, 19 mmol) was added and reacted at room temperature for 12 h. Saturated ammonium chloride was added to quench the reaction, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting product was separated and purified by column chromatography to obtain compound I-39 (2.4 g) as a white solid.

[0279] Example 6

[0280] This example is the preparation of compound I-43

[0281] The specific preparation process is as follows:

[0282] (1) Add the first solvent (pyridine, 15 mL) to the reaction flask, add the condensing agent (EDCI, 12 mmol) and the first alkaline substance (DMAP, 1.6 mmol), add compound IV'-30 and compound V'-4 (3-chloro-5-trifluoromethoxybenzoic acid) (8 mmol) and react at room temperature for 3 hours to carry out the first reaction. Then add water and extract with ethyl acetate. The organic phase is washed with saturated brine and dried over anhydrous sodium sulfate. Filter and concentrate the filtrate under reduced pressure to obtain compound III'-43.

[0283] (2) The obtained compound III'-43 was dissolved in a second solvent (glacial acetic acid, 20 mL) and refluxed at 117.9°C for 4 h for a second reaction. The mixture was cooled to room temperature, and the pH value of the system was adjusted to 9 by adding sodium hydroxide aqueous solution. The mixture was then extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain compound II (II'-43, 6.1 mmol).

[0284] (3) Compound II'-43 was dissolved in a third solvent (THF, 20 mL), and a second alkaline substance (0.76 g of mineral oil-coated NaH, NaH content 60 wt%, NaH 19 mmol) was added. After reacting at room temperature for 10 min, an ethylsulfonyl compound (ethylsulfonyl chloride, 19 mmol) was added and reacted at room temperature for 12 h. Saturated ammonium chloride was added to quench the reaction, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting product was separated and purified by column chromatography to obtain compound I-43 (2.4 g) as a white solid.

[0285] Example 7

[0286] This example is the preparation of compound I'-29

[0287] The specific preparation process is as follows:

[0288] (1) Add the first solvent (pyridine, 15 mL) to the reaction flask, add the condensing agent (EDCI, 12 mmol) and the first alkaline substance (DMAP, 1.6 mmol), add compound IV'-30 and compound V'-5 (3-chloro-5-trifluoromethylbenzoic acid) (8 mmol) and react at room temperature for 3 hours to carry out the first reaction. Then add water and extract with ethyl acetate. The organic phase is washed with saturated brine and dried over anhydrous sodium sulfate. Filter and concentrate the filtrate under reduced pressure to obtain compound III'-29.

[0289] (2) The obtained compound III'-29 was dissolved in a second solvent (glacial acetic acid, 20 mL) and refluxed at 117.9°C for 4 h for a second reaction. The mixture was cooled to room temperature, and the pH value of the system was adjusted to 9 by adding sodium hydroxide aqueous solution. The mixture was then extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain compound II (II'-29, 6.2 mmol).

[0290] (3) Compound II'-29 was dissolved in a third solvent (THF, 20 mL), and a second alkaline substance (0.76 g of mineral oil-coated NaH, NaH content 60 wt%, NaH 19 mmol) was added. After reacting at room temperature for 10 min, an ethylsulfonyl compound (ethylsulfonyl chloride, 19 mmol) was added and reacted at room temperature for 12 h. Saturated ammonium chloride was added to quench the reaction, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting product was separated and purified by column chromatography to obtain compound I-29 (2.6 g) as a white solid.

[0291] Example 8

[0292] The specific preparation process is as follows:

[0293] (1) X-1 (100 g, 0.576 mol) was dissolved in acetonitrile (650 ml), and the temperature was controlled between 13°C and 17°C in an ice-water bath. Sodium tert-butoxide (166 g, 1.73 mol) was slowly added. Ethylsulfonyl chloride (89 g, 0.69 mol) was slowly added over 10 minutes. After stirring and reacting for 2 hours, hydrochloric acid was added dropwise to adjust the pH to 3. The mixture was filtered and the filter cake was dried to obtain 112 g of a light brown solid.

[0294] 1 H NMR (500MHz, CDCl3) δ9.76 (s, 1H), 8.43 (d, J = 8.7Hz, 1H), 7.09 (d, J = 8.6Hz, 1H), 3.68 (q, J = 7.4Hz, 2H), 1.42 (t, J = 7.4Hz, 3H).

[0295] (2) Add ethanol (270 ml) to IX-1 (50 g, 0.1887 mol), add 4,4-bipyridine (9 g, 0.058 mol), slowly add tetrahydroxydiborane (47 g, 0.53 mol), react in a water bath at room temperature for 3 hours, add 500 mL of water and 500 mL of ethyl acetate to the reaction solution, extract and separate the liquids, evaporate the organic phase to dryness, and purify by column chromatography to obtain 28 g of an off-white solid.

[0296] 1 H NMR (500MHz, CDCl3) δ7.08–6.75(m,2H),6.42(s,1H),4.37–3.91(m,2H),3.34(dd,J=14.3,7.0Hz,2H),1.41(t,J=7.4Hz,3H).

[0297] (3) VIII-1 (3.7 g, 15.7 mmol) and XI-1 (3.42 g, 15.7 mol) were added to ethanol (25 mL) and refluxed for 12 h. The reaction solution was concentrated under reduced pressure and dried to obtain a crude product of VII-1. NIS (3.8 g, 16.8 mol) and 2,2,2-trifluoroethanol (30 ml) were added and reacted at room temperature for 2 h. After the reaction was completed, the reaction solution was poured into ethyl acetate (50 mL) and a saturated aqueous sodium thiosulfate solution (50 mL) was added. After extraction, the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain 3.3 g of a white solid.

[0298] Example 9

[0299] The specific preparation process is as follows:

[0300] (1) Sodium hydride (139 g, 3.48 mol, 60% content) was added to tetrahydrofuran (1 L) under nitrogen protection and cooled to 0°C in an ice bath. X-2 (200 g, 1.16 mol) was added to the reaction solution and stirred for 3 hours. Ethylsulfonyl chloride (163 g, 1.27 mol) was added dropwise. Bubbles were generated and the addition was completed within 1 hour. After stirring for half an hour, the reaction solution was slowly poured into ice water. Ethyl acetate (1 L) was added for extraction and separation. The organic phase was spin-dried and purified by column chromatography to obtain 188 g of a white solid.

[0301] 1 H NMR (500MHz, CDCl3) δ9.75 (s, 1H), 8.15 (d, J = 9.0Hz, 1H), 7.87 (d, J = 2.1Hz, 1H), 7.10 (dd, J = 9.0, 2.1Hz, 1H), 3.22 (q, J = 7.4Hz, 2H), 1.36 (t, J = 7.4Hz, 3H).

[0302] (2) IX-2 (268 g, 1.0 mol) was added to ethanol, and then iron powder (168 g, 3 mol) was added. The temperature was raised to above 60°C, and a saturated aqueous ammonium chloride solution was added dropwise. The reaction solution was heated under reflux until the solution turned reddish brown and translated for 2 hours. After the reaction was complete, the solid was filtered out by padding with diatomaceous earth. The filter cake was washed with ethyl acetate, and the filtrate was extracted with water and EA. After separation, the organic phase was evaporated to dryness and purified by column chromatography to obtain 85 g of solid.

[0303] 1 H NMR (500MHz, CDCl3) δ7.06 (d, J=2.4Hz, 1H), 7.00 (dd, J=8.6, 2.4Hz, 1H), 6.66 (d,J=8.6Hz,1H),3.90–3.37(m,2H),3.11(q,J=7.4Hz,2H),1.42–1.31(m,3H).

[0304] (3) VIII-2 (2.76 g, 12.7 mmol) was added to ethanol (10 mL), and then intermediate XI-1 (2.7 g, 11.5 mol) was added. The mixture was heated under reflux for 48 hours. The reaction solution was concentrated to dryness under reduced pressure, and tetrahydrofuran (10 mL) was added. NIS (4.27 g, 19 mmol) was added and the reaction was continued at room temperature for 6 hours. Sodium thiosulfate aqueous solution (50 mL) and ethyl acetate (50 mL) were added to the reaction solution. After extraction and separation, the organic phase was evaporated to dryness and purified by column chromatography to obtain 1.58 g (I-913) of a white solid.

[0305] Example 10

[0306] (1) IV'-3 (10.9 g, 0.1 mol) and 3,5-di-tert-butylbenzoic acid (23.4 g, 0.1 mol) were added to methanesulfonic acid (100 mL), and phosphorus pentoxide (14.2 g, 0.1 mol) was added. The reaction solution was heated to 120°C and reacted for 2 hours. The reaction solution was added to ice water and filtered under reduced pressure. The filter cake was washed with water and then dried under reduced pressure to obtain 25.2 g of an off-white solid.

[0307] 1 H NMR (500MHz, CDCl3) δ9.24(s,1H),8.27(s,1H),8.14(s,2H),7.86(s,1H),7.60(s,1H),1.35(s,18H).

[0308] (2) Sodium hydride (1.39 g, 34.8 mmol, 60% content) was added to tetrahydrofuran (10 L) under nitrogen protection and cooled to 0°C in an ice bath. II-3 (3.56 g, 1.16 mol) was added to the reaction solution and stirred for 3 hours. Ethylsulfonyl chloride (1.63 g, 12.7 mmol) was added dropwise and stirred for half an hour. The reaction solution was slowly poured into ice water and ethyl acetate (50 mL) was added for extraction. The organic phase was dried and purified by column chromatography to obtain 1.26 g of a white solid (I-433).

[0309] Example 11

[0310] Referring to the method described in Example 1, compound I-1257 was prepared using raw materials IV-1 and V-1.

[0311] Example 12

[0312] Referring to the method described in Example 1, compound I-2109 was prepared using raw materials IV-1 and V-2.

[0313] Example 13

[0314] Step 1: Dissolve 5g of 4-amino-3-nitropyridine in 30ml of DMF. The solution becomes clear and red. Slowly add 7g (2.0eq) of sodium tert-butoxide in an ice bath. The solution turns dark red with no noticeable bubbles and no temperature increase (4-5°C). After reacting for 0.5h, add 4.6g (1.0eq) of ethylsulfonyl chloride dropwise. The temperature is controlled at 15°C. The reaction is complete after 0.5h. After post-treatment, adjust the pH to 3 with HCl, then extract with water and ethyl acetate three times. The organic phase is then dried to give 2.38g of a yellow solid (yield 28.6%).

[0315] Step 2: 2.38 g of the starting material was dissolved in 20 ml of ethanol. The solution turned yellow, and the solid was not completely dissolved. 0.47 g of 4,4-bipyridine (0.3 eq) was added, followed by 2.51 g (2.8 eq) of tetrahydroxydiborane, and the reaction was allowed to proceed in an ice bath. After the addition of tetrahydroxydiborane, the temperature was raised, controlled at 10-20°C. The solution turned clear yellow, then blue, and then faded. The temperature was lowered to 12°C, indicating that the reaction was complete. The reaction solution was purified by spin drying to obtain 1.17 g of a brown oil (yield 58.2%).

[0316] Step 3: 0.5 g of amine was dissolved in 10 ml of ethanol. The solid dissolved and the solution turned yellow. 0.6 g (1 eq) of 3,5-bis(trifluoromethyl)benzaldehyde was added and heated under reflux. The solution turned yellow and the solid completely dissolved. The reaction solution was spin-dried to obtain 1.6 g of a crude brown oil (yield 100%).

[0317] Step 4: 1.6 g of raw material + 16 ml of trifluoroethanol, the solid was not completely dissolved, and the solution turned orange. 1.24 g (1.8 eq) of NIS was added, and the solution turned reddish brown. The reaction was allowed to react at room temperature for 4 h. After the spot reaction was complete, the reaction solution was poured into a beaker containing an aqueous solution of sodium thiosulfate and ethyl acetate, extracted, dried, spin-dried, and column chromatography to obtain 0.2 g of a yellow solid with a purity of 99.567% at 254 nm and 99.293% at 230 nm (yield 15%).

[0318] Example 14

[0319] Step 1: Dissolve 10g of 2-amino-3-nitropyridine in 100ml of tetrahydrofuran. The solution turns yellow, and the solid is not completely dissolved. 8.6g (3eq) of sodium hydride is slowly added in multiple batches under an ice bath. The solution turns red, with no obvious bubbles or temperature rise (4°C-5°C). After 1.5h of reaction, 11.1g (1.2eq) of ethylsulfonyl chloride is added dropwise (4°C-15°C-12°C). After 0.5h of plate reaction, the raw materials react completely. 13.3g of acetic acid is added dropwise. Lumps form and the mixture cannot be stirred upon heating. 20ml of tetrahydrofuran is added, and water is added and stirring continues. Solid precipitates, which is filtered to obtain 14.15g of a yellow-brown solid (85% yield).

[0320] Step 2: 5g of the raw material was dissolved in 50ml of ethanol. The solution turned yellow and the solid was not completely dissolved. 1g of 4,4-bipyridine (0.3eq) was added, followed by 5.4g (2.8eq) of tetrahydroxydiborane. The temperature was raised from 9°C to 80°C. As the solid was completely dissolved, the solution turned clear yellow and then blue and faded. The temperature was lowered to 12°C. After 40 minutes, the reaction of the raw material on the plate was complete. The reaction solution was dried to obtain 11g of a yellow solid. The extraction was dried to obtain 2g of a yellow solid (yield 46%).

[0321] Step 3: Dissolve 1g of amine in 20ml of ethanol. The solid is not completely dissolved and the solution turns yellow. Add 1.1g (1eq) of 3,5-di-tert-butylbenzaldehyde and heat under reflux. The solution turns yellow and the solid is completely dissolved. The reaction solution is then spun down to dryness. (Yield 100%)

[0322] Step 4: 2g of the raw material was added to 20ml of trifluoroethanol. The solid was not completely dissolved and the solution turned orange. 2g (1.8eq) of NIS was added and the solution turned dark brown. The reaction was allowed to react at room temperature for 4h. The plate was plated and the liquid was sent to the HPLC. The reaction solution was poured into a beaker containing an aqueous solution of sodium thiosulfate and ethyl acetate. The solution was extracted, dried, and spin-dried. After column chromatography, 0.25g of a yellow solid was obtained (yield 13%).

[0323] Example 15

[0324] Step 1: Weigh 4 g of N-(6-chloro-3-nitropyridin-2-yl)ethanesulfonamide, 1.55 g (1.2 eq) of cyclopropylboronic acid, 6.24 g (3 eq) of potassium carbonate, and 1.06 g (0.1 eq) of bistriphenylphosphine palladium dichloride in a mixed solvent consisting of 8 ml of 1,4-dioxane and 2 ml of aqueous solution. The reaction solution, now a cloudy yellow-brown solution, was refluxed under nitrogen. The reaction solution turned black after 45 minutes. The reaction was terminated after 3-7 hours of reaction with minimal TLC changes. Water and ethyl acetate were added to the reaction solution for extraction. The organic phase was dried, concentrated, and purified by column chromatography to afford 0.5 g of the title compound (12% yield).

[0325] Step 2: Dissolve 0.5 g of N-(6-cyclopropyl-3-nitropyridin-2-yl)ethanesulfonamide in 6 ml of anhydrous ethanol. Add 10% Pd-C to the reaction mixture. React at room temperature under hydrogen. After 1 hour, the plate shows complete reaction of the starting material, with the formation of distinct new spots. Filter the Pd-C, and concentrate the filtrate to yield 0.3 g of the title compound (68% yield).

[0326] Step 3: Dissolve 0.3g of N-(3-amino-6-cyclopropylpyridin-2-yl)ethanesulfonamide and 0.3g (1eq) of 3,5-bis(trifluoromethyl)benzaldehyde in 6ml of anhydrous ethanol and reflux for 1h 15min. The raw materials are almost completely reacted and new spots are generated. The reaction solution is dried and the crude product is used for the next step.

[0327] Step 4: Dissolve 0.6 g of (E)-N-(3-(3,5-bis(trifluoromethyl)benzylidene)amino)-6-cyclopropylpyridin-2-yl)ethanesulfonamide in 10 ml of trifluoroethanol in a single-necked flask. The solid dissolves, leaving a yellow reaction solution. Add 0.52 g (1.8 eq) of N-iodosuccinimide, causing the solution to turn purple-red. Allow the reaction to react at room temperature. After 2 h 20 min, the plate shows complete reaction of the starting material, forming a new spot. Saturated aqueous sodium thiosulfate and ethyl acetate are added to the reaction solution for extraction. The organic phase is dried and concentrated. Column chromatography yields 309.4 mg of a white product (52% yield).

[0328] Example 16

[0329] Step 1: Place 6-chloro-3-nitropyridin-2-amine (1 mol, 1.0 eq) in a three-necked glass reactor, add 10 vol of acetonitrile, cool to 0-5°C, add sodium tert-butoxide (2.5 mol, 2.5 eq), stir until homogeneous, and slowly add ethylsulfonyl chloride (1.5 mol, 1.5 eq) dropwise, maintaining the reaction system temperature below 15°C. After the addition is complete, incubate for 2 hours. After completion of the reaction, pour into water to quench, adjust the pH to acidic with aqueous hydrochloric acid, and filter the precipitated solid under reduced pressure. The resulting solid is dried and used for product synthesis.

[0330] Step 2: Dissolve N-(6-chloro-3-nitropyridin-2-yl)ethanesulfonamide (1 mmol, 1 eq) in DMSO in a three-necked flask at room temperature to obtain a solution. Add cesium carbonate (2.0 mmol, 2.0 eq) and 2,2,3,3-tetrafluoropropanol (1.5 mmol, 1.5 eq) to the solution, and stir the resulting mixture at 80°C for 4 hours. After the reaction, extract the resulting reaction solution three times with ethyl acetate. The ethyl acetate layer is washed three times with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is then evaporated under reduced pressure to obtain N-(3-nitro-6-(2,2,3,3-tetrafluoropropoxy)pyridin-2-yl)ethanesulfonamide, which is used directly in the next reaction.

[0331] Step 3: Dissolve N-(3-nitro-6-(2,2,3,3-tetrafluoropropoxy)pyridin-2-yl)ethanesulfonamide in methanol in an eggplant-shaped flask. Add 10% W palladium-on-carbon catalyst with stirring. Displace the air with a three-way connection to a hydrogen balloon, and stir at room temperature for 2 hours. After completion of the reaction, remove the palladium-on-carbon by filtration under reduced pressure. The solvent is then evaporated under reduced pressure. The resulting crude product is purified by column chromatography to yield N-(3-amino-6-(2,2,3,3-tetrafluoropropoxy)pyridin-2-yl)ethanesulfonamide, which is used in the next reaction.

[0332] Step 4: Dissolve N-(3-amino-6-(2,2,3,3-tetrafluoropropoxy)pyridin-2-yl)ethanesulfonamide (1.0 eq) in ethanol at room temperature in a three-necked flask. Add 3,5-di-tert-butylbenzaldehyde (1.0 eq) with stirring. Heat the resulting reaction mixture to reflux in ethanol for 1 hour. After the reaction is complete, remove the ethanol solvent from the reaction system under reduced pressure to obtain (E)-N-(3-((3,5-di-tert-butylbenzyl)amino)-6-(2,2,3,3-tetrafluoropropoxy)pyridin-2-yl)ethanesulfonamide, which is used directly in the next reaction.

[0333] Step 5: The obtained (E)-N-(3-((3,5-di-tert-butylbenzyl)amino)-6-(2,2,3,3-tetrafluoropropoxy)pyridin-2-yl)ethanesulfonamide was placed in a glass flask, trifluoroethanol was added for dissolution, and NIS (1.8 eq) was then added thereto and reacted at room temperature for 2 hours. After the reaction, the obtained reaction solution was quenched with an aqueous sodium sulfite solution and then extracted three times with ethyl acetate. The obtained ethyl acetate layer was first washed three times with a saturated sodium chloride solution and finally dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure to obtain the final product 2-(3,5-di-tert-butylphenyl)-3-(ethylsulfonyl)-5-(2,2,3,3-tetrafluoropropoxy)-3H-imidazo[4,5-b]pyridine, which was purified to obtain a pure product as a white solid.

[0334] Example 17

[0335] The reaction conditions are the same as those in Example 16, except that the 2,2,3,3-tetrafluoropropanol in step 2 is replaced by 2,2,2-trifluoroethanol; and the 3,5-di-tert-butylbenzaldehyde in step 4 is replaced by 3,5-bis(trifluoromethyl)benzaldehyde to obtain the target product as a white solid.

[0336] Example 18

[0337] Step 1: Dissolve N-(6-chloro-3-nitropyridin-2-yl)ethanesulfonamide (1 mmol, 1 eq) in N-methylpyrrolidone in a three-necked flask at room temperature to obtain a solution. Add sodium tert-butoxide (2.5 mmol, 2.0 eq) and propylamine hydrochloride (1.2 mmol, 1.5 eq) to the solution, and stir the resulting mixture at 80°C for 4 hours. After completion of the reaction, the resulting reaction solution was extracted three times with ethyl acetate. The resulting ethyl acetate layer was washed three times with saturated sodium chloride solution and finally dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure to obtain N-(3-nitro-6-(propylamino)pyridin-2-yl)ethanesulfonamide, which was used directly in the next reaction.

[0338] Step 2: The obtained N-(3-nitro-6-(propylamino)pyridin-2-yl)ethanesulfonamide was placed in an eggplant-shaped flask and dissolved in methanol. 10% W palladium-carbon catalyst was added under stirring. The air was displaced by connecting a three-way valve to a hydrogen balloon, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, the system was filtered under reduced pressure to remove the palladium-carbon, and the solvent was then evaporated under reduced pressure. The crude N-(3-amino-6-(propylamino)pyridin-2-yl)ethanesulfonamide was purified by column chromatography to obtain the product, which was used in the next reaction.

[0339] Step 3: Dissolve N-(3-amino-6-(propylamino)pyridin-2-yl)ethanesulfonamide (1.0 eq) in ethanol at room temperature in a three-necked flask. Add 3,5-bis(trifluoromethyl)benzaldehyde (1.0 eq) while stirring. Heat the resulting reaction mixture to reflux in ethanol for 1 hour. After the reaction is complete, cool the system to room temperature and filter under reduced pressure to obtain a yellow-green solid (E)-N-(3-((3,5-bis(trifluoromethyl)benzylidene)amino)-6-(propylamino)pyridin-2-yl)ethanesulfonamide, which is used directly in the next reaction.

[0340] Step 4: The obtained (E)-N-(3-((3,5-bis(trifluoromethyl)benzylidene)amino)-6-(propylamino)pyridin-2-yl)ethanesulfonamide was placed in a glass flask, trifluoroethanol was added for dissolution, and NIS (1.8eq) was then added thereto and reacted at room temperature for 2 hours. After the reaction, the obtained reaction solution was quenched with an aqueous sodium sulfite solution, and then extracted three times with ethyl acetate. The obtained ethyl acetate layer was first washed three times with a saturated sodium chloride solution, and finally dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure to obtain the final product 2-(3,5-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)-6-iodo-N-propyl-3H-imidazo[4,5-b]pyridin-5-amine, which was purified to obtain a pure product as a white solid.

[0341] Example 19

[0342] Step 1: Take a three-necked glass reactor, add N-(6-chloro-3-nitropyridin-2-yl)ethanesulfonamide (1mmol, 1eq) and cyclopentane at room temperature, add anhydrous potassium carbonate (0.2mmol, 0.2eq) and anhydrous potassium fluoride (2mmol, 2.0eq) under stirring, and heat the resulting mixture to 150 degrees for 4 hours. After the reaction is completed, the resulting reaction solution is cooled to room temperature, ethyl acetate and saturated sodium carbonate aqueous solution are added, filtered through diatomaceous earth, and the resulting filtrate is extracted three times with ethyl acetate. The aqueous phase is adjusted to a weakly acidic pH with hydrochloric acid and then extracted again with ethyl acetate. The ethyl acetate phase obtained this time is washed three times with a saturated aqueous ammonium chloride solution, dried over anhydrous sodium sulfate, and the solvent is evaporated under reduced pressure to obtain a yellow solid product N-(6-fluoro-3-nitropyridin-2-yl)ethanesulfonamide.

[0343] Step 2: The resulting N-(6-fluoro-3-nitropyridin-2-yl)ethanesulfonamide was placed in an eggplant-shaped flask and dissolved in methanol. A 10% W palladium-on-carbon catalyst was added with stirring. The air was displaced through a three-way connection connected to a hydrogen balloon, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the palladium-on-carbon was removed by filtration under reduced pressure, and the solvent was evaporated under reduced pressure. The crude N-(3-amino-6-fluoropyridin-2-yl)ethanesulfonamide was purified by column chromatography to obtain the product for use in the next reaction.

[0344] Step 3: Dissolve N-(3-amino-6-fluoropyridin-2-yl)ethanesulfonamide (1.0 eq) in ethanol at room temperature in a three-necked flask. Add 3,5-di-tert-butylbenzaldehyde (1.0 eq) while stirring. Heat the resulting reaction mixture to reflux in ethanol for 1 hour. After the reaction is complete, remove the ethanol solvent from the reaction system under reduced pressure to obtain (E)-N-(3-((3,5-di-tert-butylbenzyl)amino)-6-fluoropyridin-2-yl)ethanesulfonamide, which is used directly in the next reaction.

[0345] Step 4: The obtained (E)-N-(3-((3,5-di-tert-butylbenzyl)amino)-6-fluoropyridin-2-yl)ethanesulfonamide was placed in a glass flask, trifluoroethanol was added for dissolution, and NIS (1.8 eq) was then added thereto and reacted at room temperature for 2 hours. After the reaction, the obtained reaction solution was quenched with an aqueous sodium sulfite solution and then extracted three times with ethyl acetate. The obtained ethyl acetate layer was first washed three times with a saturated sodium chloride solution and finally dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure to obtain the final product 2-(3,5-di-tert-butylphenyl)-3-(ethylsulfonyl)-5-fluoro-3H-imidazole[4,5-b]pyridine, which was purified by column chromatography to obtain a pure product as a white solid.

[0346] Example 20

[0347] Step 1: In a three-necked glass reactor, dissolve N-(6-chloro-3-nitropyridin-2-yl)ethanesulfonamide (1 mmol, 1 eq) in ethanol at room temperature. Add anhydrous sodium sulfide (1.5 mmol, 1.5 eq) while stirring, and heat the reaction system to 80°C for 30 minutes. After the reaction is complete, quench the reaction system by adding water, and adjust the pH to acidic with aqueous hydrochloric acid. The resulting solid is filtered under reduced pressure and dried to obtain a purple solid, the product N-(6-mercapto-3-nitropyridin-2-yl)ethanesulfonamide, which is used directly in the next reaction.

[0348] Step 2: The above-mentioned product N-(6-mercapto-3-nitropyridin-2-yl)ethanesulfonamide (1eq) was dissolved in DMF, potassium carbonate (2.0eq) and iodoethane (1.5eq) were added under stirring, and the reaction solution was placed at room temperature for 4 hours. After the reaction, the reaction system was poured into water to quench, the pH was adjusted to acidic with hydrochloric acid, and then extracted three times with ethyl acetate. The obtained ethyl acetate phase was washed with saturated ammonium chloride aqueous solution and then dried over anhydrous sodium sulfate. The organic phase was evaporated to dryness under reduced pressure to obtain N-(6-(ethylthio)-3-nitropyridin-2-yl)ethanesulfonamide product, which was purified by column chromatography to obtain a pure product.

[0349] Step 3: The obtained N-(6-(ethylthio)-3-nitropyridin-2-yl)ethanesulfonamide (1.0 eq) product solution was added to a dichloromethane solution, and the oxidant m-chloroperbenzoic acid (MCPBA 3.0 eq) was added and reacted at room temperature for 4 hours. After the reaction was completed, the reaction was quenched with an aqueous sodium sulfite solution and extracted three times with ethyl acetate. The resulting organic phase was washed with a saturated aqueous ammonium chloride solution, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure to obtain the N-(3-amino-6-(ethylsulfonyl)pyridin-2-yl)ethanesulfonamide product, which was used directly in the next step.

[0350] Step 4: The obtained N-(3-amino-6-(ethylsulfonyl)pyridin-2-yl)ethanesulfonamide product was placed in an eggplant-shaped flask and dissolved in methanol. 10% W palladium-carbon catalyst was added under stirring. The air was replaced by connecting a three-way valve to a hydrogen balloon, and the reaction was stirred at room temperature for 2 hours. After the reaction was completed, the system was filtered under reduced pressure to remove the palladium-carbon, and the solvent was then evaporated under reduced pressure. After purification by column chromatography, the N-(3-amino-6-(ethylsulfonyl)pyridin-2-yl)ethanesulfonamide product was obtained and used in the next step.

[0351] Step 5: The reaction conditions are the same as those in Step 4 of Example 16, except that 3,5-di-tert-butylbenzaldehyde is replaced with 3,5-bis(trifluoromethyl)benzaldehyde to obtain the product (E)-N-(3-((3,5-bis(trifluoromethyl)benzylidene)amino)-6-(ethylsulfonyl)pyridin-2-yl)ethanesulfonamide, which is directly used in the next step.

[0352] Step 6: The reaction was carried out in the same manner as in Step 5 of Example 16. After purification by chromatography, the product, 2-(3,5-bis(trifluoromethyl)phenyl)-3,5-bis(ethylsulfonyl)-3H-imidazo[4,5-b]pyridine, was obtained as a white solid. The preparation methods of representative compounds of the present invention are listed above. The preparation of other compounds can refer to the methods of Examples 1-20, simply substituting commercially available starting materials. The mass spectrometry and hydrogen spectrum data of some compounds of the present invention are shown in Table 27.

[0353] Table 27

[0354] Biological activity test

[0355] This test example tests the acaricidal activity of the compound prepared above, specifically the acaricidal activity against Tetranychus cinnabarinus. The specific test process is as follows:

[0356] (1) The test compound was dissolved in acetone and diluted with a 0.1 wt % Tween 80 aqueous solution to the desired concentration (see Test Examples 1-A to 1-C below), with the acetone content not exceeding 5 wt %, to prepare a pharmaceutical agent;

[0357] (2) Remove one true leaf from the bean seedlings that have grown to two true leaves, inoculate with Tetranychus cinnabarinus (the number of Tetranychus cinnabarinus mites inoculated per bean seedling is 25-100), and investigate the base number of inoculated mites 24 hours later. Use a handheld sprayer to spray the agent prepared in step (1) on the entire plant of three bean seedlings (the spray volume for each plant is 0.5 mL). After treatment, place them in a constant temperature observation room (25°C) for observation. After 72 hours, investigate the number of live mites and calculate the mortality rate:

[0358] Lethality rate (%) = (number of inoculated mites - number of live mites after spraying) / number of inoculated mites × 100%.

[0359] Test Example 1-A

[0360] The agent was diluted to a test compound concentration of 100 mg / L and then tested according to the above procedure. In this test, compounds I-3054, I-3037, I-3057, I-3055, I-3017, I-3008, I-3009, I-3060, I-3044, I-3048, I-2436, I-3052, I-1143, I-3051, and I-3053 showed greater than 90% mortality against adult Tetranychus cinnabarinus mites.

[0361] The agent was diluted to a test compound concentration of 25 mg / L and then tested according to the above procedure. In this test, compounds I-513, I-3015, I-3016, I-3012, I-3007, I-3054, and I-3028 showed a mortality rate greater than 90% against adult Tetranychus cinnabarinus mites.

[0362] The compounds were diluted to a test compound concentration of 25 mg / L and then tested according to the above procedure. In this test, compounds I-2, I-29, I-30, I-39, I-43, I-50, I-433, I-913, I-1257, I-1408, I-1462, I-1489, I-1516, I-1570, I-2109, I-2113, I-2117, I-2143, I-2164, I-2188, and I-2242 showed 100% lethality against adult Tetranychus cinnabarinus mites.

[0363] The compounds were diluted to a concentration of 6.25 mg / L and then tested according to the above procedure.

[0364] In this test assay, compounds I-2, I-29, I-30, I-39, I-43, I-50, I-66, I-57, I-77, I-3005, I-3038, I-3036, I-3001, I-3002, I -613, I-3039, I-633, I-3040, I-3018, I-333, I-3006, I-3041, I-3045, I-313, and I-3046 showed a lethality rate of greater than 90% against adult spider mites.

[0365] Test Example 1-B

[0366] The reagent was diluted to a concentration of 0.78 mg / L of the test compound, and then the test was performed according to the above process.

[0367] In this test, compounds I-2, I-29, I-30, I-39, I-43, and I-50 showed a mortality rate of more than 90% against adult Tetranychus cinnabarinus mites.

[0368] According to the above test method, compounds I-2, I-29, I-30, I-39, I-43, I-50, I-333, I-3041, CK1 and CK2 were selected for parallel tests on mites (Tetranychus cinnabarinus). The test results are shown in Table 28 below:

[0369] Table 28

[0370] In Table 28, the structure of CK1 is The structure of CK2 is

[0371] It can be seen from the above test results that the compounds or salts thereof provided by the present invention have excellent insecticidal and acaricidal effects, and the insecticidal and acaricidal activity is significantly higher than that of known compounds. In particular, when the compounds of the present invention are used at very low concentrations (such as 0.78 mg / L), they can have excellent insecticidal and acaricidal effects.

[0372] The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, various simple variations of the technical solution of the present invention may be made, including combining the various technical features in any other appropriate manner. These simple variations and combinations should also be regarded as disclosed in the present invention and fall within the scope of protection of the present invention.

Claims

1. An aromatic heterocyclic compound and / or its salt, characterized in that: The aromatic heterocyclic compound has a structure shown in formula (I): Wherein, R is selected from substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkynyl, substituted or unsubstituted phenyl, wherein the substituted substituents are each independently selected from halogen, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 Cycloalkoxy; X 1 Select from N or CY 1 , X 2 Select from N or CY 2 , X 3 Select from N or CY 3 , X 4 Select from N or CY 4 ; where X 1 , X 2 , X 3 and X 4 At least one of them is selected from N; Y 1 , Y 2 , Y 3 , Y 4 are each independently selected from H, halogen, CN, NO2, formyl, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Alkylthio, substituted or unsubstituted C1-C 10 Alkylsulfinyl, substituted or unsubstituted C1-C 10 Alkylsulfonyl, substituted or unsubstituted C1-C 10 Alkylcarbonyl, substituted or unsubstituted C1-C 10 alkoxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C2-C6 alkenyloxy, substituted or unsubstituted C2-C6 alkynyloxy, substituted or unsubstituted C1-C 10 Alkylcarbonyloxy, substituted or unsubstituted C1-C 10 Cyanoalkyl, substituted or unsubstituted C1-C 10 substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryl C1-C6 alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C1-C6 alkoxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylthio, substituted or unsubstituted aryl C1-C6 alkylsulfonyl, substituted or unsubstituted aryl C1-C6 alkylsulfinyl, substituted or unsubstituted aryl C1-C6 alkylthio, substituted or unsubstituted heterocycle, substituted or unsubstituted heterocycle C1-C6 alkyl, substituted or unsubstituted heterocyclicoxy, wherein each group of the substituted substituents is independently selected from halogen, unsubstituted C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 At least one of cycloalkoxy; optionally, Y 1 and Y 2 , Y 2 and Y 3 , Y 3 and Y 4 , Y 4 and Y 5 Can be divided into four groups, at least one of which is consistent with X in formula (I) 1 To X 4 The aromatic rings that are composed together are cyclized to form at least one 3- to 8-membered ring via or without at least one heteroatom; Q is selected from the following aromatic rings: In Q1, Z 1 Select from N or CT 1 , Z 2 Select from N or CT 2 , Z 3 Select N or CT 3 , Z 4 Select from N or CT 4 , Z 5 Select from N or CT 5 ; In the Q1 ring, the number of N atoms does not exceed 4; In Q2, Z 1 Selected from N, NR 1 , O, S or CT 1 , Z 2 Selected from N, NR 2 , O, S or CT 2 , Z 3 Selected from N, NR 3 , O, S or CT 3 , Z 4 Selected from N, NR 4 , O, S or CT 4 ; In the Q2 ring, the number of O or S atoms does not exceed 1; In Q3, Z 1 Selected from N, NR 1 , O, S or CT 1 , Z 2 Selected from N, NR 2 , O, S or CT 2 , Z 3 Selected from N, NR 3 , O, S or CT 3 , Z 4 Selected from N, NR 4 , O, S or CT 4 ; In the Q3 ring, the number of O or S atoms does not exceed 1, and the number of N atoms does not exceed 4; T 1 , T 2 , T 3 , T 4 , T 5 are each independently selected from H, halogen, CN, NO2, formyl, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Alkylthio, substituted or Unsubstituted C1-C 10 Alkylsulfinyl, substituted or unsubstituted C1-C 10 Alkylsulfonyl, substituted or unsubstituted C1-C 10 Alkylcarbonyl, substituted or unsubstituted C1-C 10 alkoxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C2-C6 alkenyloxy, substituted or unsubstituted C2-C6 alkynyloxy, substituted or unsubstituted C1-C 10 Alkylcarbonyloxy, substituted or unsubstituted C1-C 10 Cyanoalkyl, substituted or unsubstituted C1-C 10 substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryl C1-C6 alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C1-C6 alkoxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylthio, substituted or unsubstituted aryl C1-C6 alkylsulfonyl, substituted or unsubstituted aryl C1-C6 alkylsulfinyl, substituted or unsubstituted aryl C1-C6 alkylthio, substituted or unsubstituted heterocycle, substituted or unsubstituted heterocycle C1-C6 alkyl, substituted or unsubstituted heterocyclicoxy, wherein the substituted substituents are each independently selected from halogen, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, halogenated C3-C 10 Cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, C3-C 10 Cycloalkoxy, halogenated C3-C 10 Cycloalkoxy; optionally, T 1 and T 2 , T 2 and T 3 , T 3 and T 4 , T 4 and T 5 It can be divided into four groups, wherein at least one group of carbon atoms connected thereto are cyclized to form at least one 3- to 8-membered ring via or without at least one heteroatom; R 1 , R 2 , R 3 and R 4 Each of the substituted substituents is independently selected from H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C1-C6 alkylsulfinyl, substituted or unsubstituted C1-C6 alkylsulfonyl or substituted or unsubstituted phenyl; wherein the substituted substituents are independently selected from halogen, CN, NO2, formyl, C1-C6 alkyl, halogenated C1-C6 alkyl, -At least one of C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C3-C6 cycloalkyloxy, halogenated C3-C6 cycloalkoxy, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C1-C6 alkylcarbonyloxy or cyano C1-C6 alkoxy.

2. The compound and / or its salt according to claim 1, wherein In formula (I), R is selected from substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted phenyl, wherein the substituted substituents are each independently selected from at least one of halogen, C1-C3 alkyl, halo-C1-C3 alkyl, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, C1-C3 alkoxy, halo-C1-C3 alkoxy, C3-C6 cycloalkyloxy or halo-C3-C6 cycloalkyloxy; and / or, Y 1 , Y 2 , Y 3 , Y 4 Each is independently selected from H, halogen, CN, NO2, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl substituted C1-C6 alkyl, halogenated C3-C6 cycloalkyl substituted C1-C6 alkyl, C3-C6 cycloalkyl substituted halogenated C1-C6 alkyl, C1-C6 alkoxy substituted C1-C6 alkyl, halogenated C1-C6 alkoxy substituted C1-C6 alkyl, C1-C6 alkoxy substituted halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkyl substituted C 3-C6 cycloalkyl, halogenated C1-C6 alkyl-substituted C3-C6 cycloalkyl, C1-C6 alkyl-substituted halogenated C3-C6 cycloalkyl, C1-C6 alkyl-substituted halogenated C3-C6 cycloalkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C1-C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, formyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxy alkylcarbonyl, arylcarbonyl, aryloxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, halogenated C2-C6 alkenyloxy, halogenated C2-C6 alkynyloxy, C1-C8 alkylcarbonyloxy, halogenated C1-C6 alkylcarbonyloxy, cyano C1-C6 alkyl, cyano C1-C6 alkoxy, C1-C6 alkyl-substituted silanyl, substituted or unsubstituted amino, aryl, aryl C1-C6 alkyl, aryloxy, aryl C1-C8 -C6 alkoxy, arylsulfonyl, arylsulfinyl, arylthio, arylC1-C6 alkylsulfonyl, arylC1-C6 alkylsulfinyl, arylC1-C6 alkylthio, heterocyclicC1-C6 alkyl, heterocyclicoxy, wherein the substituted substituents are each independently selected from at least one of halogen, C1-C6 alkyl, haloC1-C6 alkyl, C3-C6 cycloalkyl, haloC3-C6 cycloalkyl, C1-C6 alkoxy, haloC1-C6 alkoxy, C3-C6 cycloalkyloxy or haloC3-C6 cycloalkyloxy; and / or, T 1 , T 2 , T 3 , T 4 , T 5 Each is independently selected from H, halogen, CN, NO2, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl substituted C1-C6 alkyl, halogenated C3-C6 cycloalkyl substituted C1-C6 alkyl, C3-C6 cycloalkyl substituted halogenated C1-C6 alkyl, C1-C6 alkoxy substituted C1-C6 alkyl, halogenated C1-C6 alkoxy substituted C1-C6 alkyl, C1-C6 alkoxy substituted halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 C1-C6 alkyl, C1-C6 alkyl substituted C3-C6 cycloalkyl, halogenated C1-C6 alkyl substituted C3-C6 cycloalkyl, C1-C6 alkyl substituted halogenated C3-C6 cycloalkyl, C1-C6 alkyl, halogenated C1-C6 alkoxy, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C1-C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, formyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, halogenated C2-C6 alkenyloxy, halogenated C2-C6 alkynyloxy, C1-C6 alkylcarbonyloxy, halogenated C1-C6 alkylcarbonyloxy, cyano C1-C6 alkyl, cyano C1-C6 alkoxy, C1-C6 alkyl-substituted silyl, substituted or unsubstituted amino, aryl, arylC1-C6 -C6 alkyl, aryloxy, aryl C1-C6 alkoxy, aryl sulfonyl, aryl sulfinyl, arylthio, aryl C1-C6 alkylsulfonyl, aryl C1-C6 alkylsulfinyl, aryl C1-C6 alkylthio, heterocycle, heterocycle C1-C6 alkyl, heterocycleoxy, and the optional substituents are each independently selected from at least one of halogen, C1-C6 alkyl, halo-substituted C1-C6 alkyl, C3-C6 cycloalkyl, halo-substituted C3-C6 cycloalkyl, C1-C6 alkoxy, halo-substituted C1-C6 alkoxy, C3-C6 cycloalkyloxy or halo-substituted C3-C6 cycloalkyloxy.

3. The compound and / or salt thereof according to claim 1 or 2, wherein In formula (I), R is selected from C1-C4 alkyl or halogenated C1-C4 alkyl; or substituted or unsubstituted phenyl, wherein the substituted substituents are each independently selected from at least one of halogen, C1-C3 alkyl, halogenated C1-C3 alkyl, C1-C3 alkoxy, and halogenated C1-C3 alkoxy; and / or, Y 1 , Y 2 , Y 3 , Y 4 Each is independently selected from H, halogen, CN, NO2, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted amino, C1-C4 alkoxy C1-C4 alkyl, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C1-C6 -C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or halogenated C1-C6 alkylsulfonyl; wherein the substituted substituents are each independently selected from at least one of halogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C3-C6 cycloalkyloxy or halogenated C3-C6 cycloalkyloxy; and / or, T 1 , T 2 , T 3 , T 4 , T 5 Each is independently selected from H, halogen, CN, NO2, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C1-C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or halogenated C1-C6 alkylsulfonyl.

4. The compound and / or salt thereof according to any one of claims 1 to 3, wherein In formula (I), R is selected from C1-C4 alkyl, halogenated C1-C4 alkyl or phenyl; and / or, Y 1 , Y 2 , Y 3 , Y 4 Each independently selected from H, halogen, CN, NO2, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C1-C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl or halogenated C1-C6 alkylsulfonyl; and / or, T 1 , T 2 , T 3 , T 4 , T 5 Each is independently selected from H, halogen, CN, NO2, CH3, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, cyclopropyl, CF3, CHF2, 2,2,2-trifluoroethyl, heptafluoroisopropyl, OCH3, tert-butoxy, OCHF2, OCF3, 2,2,2-trifluoroethoxy, heptafluoroisopropoxy, SCH3, SCH2CH3, SCHF2, SCF3, 2,2,2-trifluoroethylthio, heptafluoroisopropylthio, trifluoromethanesulfinyl, trifluoromethanesulfonyl, trifluoroethanesulfinyl or trifluoroethanesulfonyl.

5. The compound and / or salt thereof according to any one of claims 1 to 4, wherein In formula (I), R is selected from methyl, ethyl, chloroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl or phenyl; and / or, Y 1 , Y 2 , Y 3 , Y 4 Each independently selected from H, halogen, CN, NO2, CH3, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, cyclopropyl, CF3, CHF2, 2,2,2-trifluoroethyl, heptafluoroisopropyl, OCH3, tert-butoxy, OCHF2, OCF3, 2,2,2-trifluoroethoxy, heptafluoroisopropoxy, SCH3, SCH2CH3, SCHF2, SCF3, 2,2,2-trifluoroethylthio, heptafluoroisopropylthio, trifluoromethanesulfinyl, trifluoromethanesulfonyl, trifluoroethanesulfinyl or trifluoroethanesulfonyl.

6. The compound and / or salt thereof according to any one of claims 1 to 5, wherein The compound of the structure shown in formula (I) is selected from the compounds shown in any of the following structures, Preferably 7. The compound and / or salt thereof according to any one of claims 1 to 6, wherein Q is selected from the following aromatic rings: Preferably Preferably, R 1 , R 2 , R 3 and R 4 Each is independently selected from H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkylsulfinyl, substituted or unsubstituted C1-C6 alkylsulfonyl or substituted or unsubstituted phenyl; wherein the substituted substituents are each independently selected from at least one of halogen, CN, NO2, formyl, C1-C3 alkyl or halogenated C1-C3 alkyl; More preferably, R 1 , R 2 , R 3 and R 4 Each is independently selected from H, C1-C6 alkyl, halogenated C1-C6 alkyl, substituted or unsubstituted C1-C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, phenyl or halogenated phenyl; More preferably, R 1 , R 2 , R 3 and R 4 Each is independently selected from H, CH3, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, CF3, 2,2,2-trifluoroethyl, heptafluoroisopropyl, trifluoromethanesulfinyl, trifluoromethanesulfonyl, phenyl, trifluoroethanesulfinyl or trifluoroethanesulfonyl.

8. The compound and / or salt thereof according to any one of claims 1 to 7, characterized in that The compound of formula I has the structure shown in the compound of formula IA, R is selected from methyl, ethyl, chloroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, allyl, propargyl, trifluoromethyl or phenyl; Y 2 , Y 3 , Y 4 Each independently selected from H, halogen, CN, NO2, CH3, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, cyclopropyl, CF3, CHF2, 2,2,2-trifluoroethyl, heptafluoroisopropyl, OCH3, tert-butoxy, OCHF2, OCF3, 2,2,2-trifluoroethoxy, heptafluoroisopropoxy, SCH3, SCH2CH3, SCHF2, SCF3, 2,2,2-trifluoroethylthio, heptafluoroisopropylthio, trifluoromethanesulfinyl, trifluoromethanesulfonyl, trifluoroethanesulfinyl or trifluoroethanesulfonyl; T 1 , T 2 , T 3 , T 4 , T 5 Each is independently selected from H, halogen, CN, NO2, CH3, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, neopentyl, cyclopropyl, CF3, CHF2, 2,2,2-trifluoroethyl, heptafluoroisopropyl, OCH3, tert-butoxy, OCHF2, OCF3, 2,2,2-trifluoroethoxy, heptafluoroisopropoxy, SCH3, SCH2CH3, SCHF2, SCF3, 2,2,2-trifluoroethylthio, heptafluoroisopropylthio, trifluoromethanesulfinyl, trifluoromethanesulfonyl, trifluoroethanesulfinyl or trifluoroethanesulfonyl.

9. A method for preparing aromatic heterocyclic compounds and / or their salts, characterized in that: The method includes: (1) in a first solvent, in the presence of a first alkaline substance and a condensing agent, subjecting compound V and compound IV to a condensation reaction to obtain compound III; (2) in a second solvent, subjecting the compound III to a cyclization reaction with an acidic substance to obtain a compound II; (3) in a third solvent, in the presence of a second alkaline substance, subjecting the compound II to a sulfonylation reaction with a sulfonyl group-containing compound to obtain a compound I; Wherein, the compound V has a structure shown in formula (V), the compound IV has a structure shown in formula (IV), the compound III has a structure shown in formula (III), the compound II has a structure shown in formula (II), the compound I has a structure shown in formula (I), and the sulfonyl-containing compound has a structure shown in formula (VI); In formula (I), formula (II), formula (III), formula (IV), formula (V) and formula (VI), R, X 1 , X 2 , X 3 , X 4 , Q has the same definition as that in any one of claims 1 to 8, and L is selected from halogen.

10. The method according to claim 9, wherein: In step (1), the conditions of the condensation reaction include: temperature of -10°C to 150°C, reaction time of 0.5-48h; and / or, the molar ratio of the compound V to the compound IV is 0.5-2:1; And / or, the condensing agent is selected from at least one of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide or its hydrochloride, carbonyldiimidazole, 1,3-dicyclohexylcarbodiimide, diethyl cyanophosphate, chlorocarbonate compounds, and 2-chloro-1-methylpyridinium iodide; and / or, the molar ratio of the condensing agent to the compound IV is 1-2:1; and / or, the first alkaline substance is at least one selected from pyridine, dimethylaminopyridine, triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene; And / or, the molar ratio of the first alkaline substance to the compound IV is 0.1-10:

1.

11. The method according to claim 9 or 10, wherein: In step (2), the conditions of the cyclization reaction include: temperature of -10°C to 300°C, reaction time of 0.5-48h; And / or, the acidic substance is selected from at least one of p-toluenesulfonic acid or its hydrate, methanesulfonic acid, trifluoromethanesulfonic acid, hydrochloric acid, sulfuric acid, nitric acid, formic acid, acetic acid, propionic acid, trifluoroacetic acid, trichloroacetic acid, benzoic acid, and phosphoric acid; And / or, the molar ratio of the acidic substance to the compound IV is 0.01-10:

1.

12. The method according to any one of claims 9 to 11, wherein: In step (3), the conditions of the sulfonylation reaction include: temperature of -10°C to 100°C, reaction time of 0.5-48h; and / or, the molar ratio of the sulfonyl-containing compound to the compound II is 0.8-10:1; and / or, the second alkaline substance is at least one selected from pyridine, dimethylaminopyridine, triethylamine, diisopropylethylamine, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene; And / or, the molar ratio of the second alkaline substance to the compound II is 1-10:

1.

13. A method for preparing aromatic heterocyclic compounds and / or their salts, characterized in that: The method includes: (a) in the presence of a fourth solvent and a third basic substance, subjecting compound X and compound VI to a condensation reaction; (b) subjecting the product compound IX of the condensation reaction in step (a) to a reduction reaction with a reducing substance in the presence of a fifth solvent; (c) subjecting the reduction product compound VIII of step (b) and compound XI to a condensation reaction in the presence of a sixth solvent; (d) subjecting the product compound VII of the condensation reaction in step (c) to an addition ring-closing reaction in the presence of a seventh solvent; Wherein, the compound I has a structure shown in formula (I), the compound VII has a structure shown in formula (VII), the compound VIII has a structure shown in formula (VIII), the compound IX has a structure shown in formula (IX), the compound X has a structure shown in formula (X), the compound XI has a structure shown in formula (XI), and the compound VI has a structure shown in formula (VI); Among them, R, X 1 , X 2 , X 3 , X 4 , the definition of Q is the same as that in any one of claims 1-8, and L is selected from halogen.

14. The method according to claim 13, wherein: The third alkaline substance is selected from at least one of pyridine, dimethylaminopyridine, triethylamine, diisopropylethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide and 1,8-diazabicyclo[5.4.0]undec-7-ene; and / or, the molar ratio of the compound X to the compound VI is 0.5-2:1; And / or, in step (a), the conditions of the condensation reaction include: temperature of -20°C to 150°C, and reaction time of 0.1-48h.

15. The method according to claim 13 or 14, wherein: The reducing substance is selected from at least one of hydrogen, metal, sulfide, borane and its complex and hydrosulfite; And / or, in step (b), the conditions of the reduction reaction include: temperature of -10°C to 200°C, and reaction time of 0.5-72h.

16. The method according to any one of claims 13 to 15, wherein: The molar ratio of the compound VIII to the compound XI is 0.5-2:1; and / or, the reaction in step (c) may be carried out in the presence of a first catalyst; and / or, the first catalyst is selected from at least one of glacial acetic acid, propionic acid, amino acid and Lewis acid; And / or, in step (c), the conditions of the condensation reaction include: temperature of -20°C to 150°C, and reaction time of 0.1-48h.

17. The method according to any one of claims 13 to 16, wherein: The reaction described in step (d) may be carried out in the presence of a second catalyst; and / or, the second catalyst is selected from iodide, bromide, glacial acetic acid, propionic acid, amino acid, Lewis acid; and / or, the fourth to seventh solvents are each independently selected from at least one of methanol, ethanol, isopropanol, propanol, butanol, dichloromethane, chloroform, carbon tetrachloride, ethylene dichloride, ethyl acetate, toluene, xylene, acetonitrile, tetrahydrofuran, acetone, N,N-dimethylformamide, N-methylpyrrolidone, dioxane and water; And / or, in step (d), the conditions of the condensation reaction include: temperature of -20°C to 150°C, and reaction time of 0.1-48h.

18. Use of the aromatic heterocyclic compound and / or its salt according to any one of claims 1 to 8 in the preparation of insecticides and acaricides.

19. An insecticide and acaricide, characterized in that: The insecticide and acaricide contains an active ingredient, wherein the active ingredient is selected from at least one of the aromatic ring compounds and / or salts thereof according to any one of claims 1 to 8; Preferably, based on the total weight of the insecticide and acaricide, the content of the active ingredient is 1-99% by weight, more preferably 5-60% by weight. weight%.

20. Use of the insecticide and acaricide according to claim 19 for killing insects and / or acaricides in agriculture, forestry and gardening.

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