Insecticides and acaricides and their uses

Abstract

The present invention provides a benzimidazole compound represented by formula (I) or a salt thereof, a process for its preparation, and uses. The benzimidazole compound or its salt has excellent insecticidal and acaricidal effects, and can exhibit acaricidal effects even when used at a particularly low concentration. [Formula 1] TIFF2024507409000034.tif34170

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of Chinese patent application No. 202110204832.5, filed on February 23, 2021, the contents of which are incorporated herein by reference.

[0002] The present invention relates to the field of insecticides, in particular , kill Concerning insecticides and acaricides and their uses. [Background technology]

[0003] In agricultural and horticultural crop production, damage caused by pests is significant, and pests that are resistant to existing chemicals are appearing. From the perspective of the impact on environmental organisms and labor saving, there are hopes for the development of agricultural and horticultural insecticides and acaricides that have new modes of action, have little effect on natural enemies and beneficial insects, and have systemic and translocating activity.

[0004] The following benzimidazole compounds are reported in Advanced Materials Research Vols 236-238 (2011) pp2570-2573, some of which have anti-inflammatory activity, but there is no disclosure of their insecticidal or acaricidal activity.

[0005] [ka]

[0006] There is currently a need to provide compounds that have high insecticidal and acaricidal activity when used at low concentrations. Summary of the Invention [Problem to be solved by the invention]

[0007] The object of the present invention is to solve the defect of conventional benzimidazole compounds that they only have insecticidal / acaricidal activity when used in high concentrations, and therefore cannot meet the need to control pests and mites in fields, and to provide novel benzimidazole compounds and salts thereof which are expected to be used as active ingredients in insecticides and acaricides and which can provide high control effects even when used in low concentrations (100 ppm or less). [Means for solving the problem]

[0008] In order to achieve the above object, a first aspect of the present invention provides a benzimidazole compound having a structure represented by formula (I) or a salt thereof.

[0009] [ka]

[0010] (In formula (I), R is a 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, and the optional substituents are each independently selected from halogen, C1-C 10 Alkyl, halo C1~C 10 Alkyl, C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkyl, C1-C 10 Alkoxy, Halo C1~C 10 Alkoxy, C3-C 10 Cycloalkoxy, haloC3~C 10 At least one selected from cycloalkoxy; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 are each independently H, halogen, CN, NO2, formyl, or a substituted or unsubstituted C1-C 10Alkyl, 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 each set of optional substituents is independently selected from halogen, C1-C6 alkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyl C1-C6 alkyl, substituted or unsubstituted heterocyclyloxy, and each set of optional substituents is independently selected from halogen, C1-C6 alkyl, substituted or unsubstituted aryloxy ... 10 Alkyl, halo C1-C 10 Alkyl, C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkyl, C1-C 10 Alkoxy, Halo C1~C 10 Alkoxy, C3-C 10 Cycloalkoxy, haloC3~C 10cycloalkoxy; and optionally, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 any two adjacent groups among the above are grouped into one pair, and at least one pair is cyclized with the benzene ring to which it is bonded, with or without at least one heteroatom therebetween, to form at least one 3- to 8-membered ring; Z 1 , Z 2 , Z 3 , Z 4 are each independently H, halogen, CN, NO2, formyl, or a 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 10each set of optional substituents is independently selected from halogen, 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 heterocyclyl, substituted or unsubstituted heterocyclyl C1-C6 alkyl, substituted or unsubstituted heterocyclyloxy, and 10 Alkyl, halo C1~C 10 Alkyl, C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkyl, C1-C 10 Alkoxy, Halo C1~C 10 Alkoxy, C3-C 10 Cycloalkoxy, haloC3~C 10 cycloalkoxy; and optionally, Z 1 , Z 2 , Z 3 , Z 4 any two adjacent groups among the above are grouped into one pair, and at least one pair is cyclized with the benzene ring to which it is bonded, with or without at least one heteroatom therebetween, to form at least one 3- to 8-membered ring; And Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 3 , Y 4 are all H and R is ethyl, then Y 5 is not H, fluorine or chlorine, but Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 4 , Y5 are all H and R is ethyl, then Y 3 is not fluorine or chlorine, Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 3 , Y 5 are all H and R is ethyl, then Y 2 , Y 4 is not chlorine at the same time.)

[0011] A second aspect of the present invention is (1) performing a first reaction between compound V and compound IV in a first solvent in the presence of a first alkaline substance and a condensing agent to obtain compound III; (2) performing a second reaction between the compound III and an acidic substance in a second solvent to obtain a compound II; and (3) performing a third reaction of compound II with a sulfonyl-containing compound in a third solvent in the presence of a second alkaline material to obtain the benzimidazole compound, The present invention provides a method for preparing a benzimidazole compound, wherein compound V has a structure represented by formula (V), compound IV has a structure represented by formula (IV), compound III has a structure represented by formula (III), compound II has a structure represented by formula (II), the benzimidazole compound has a structure represented by formula (I), and the sulfonyl-containing compound has a structure represented by formula (VI).

[0012] [ka]

[0013] (In the formula (I), formula (II), formula (III), formula (IV), formula (V), and formula (VI), R, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Z 1 , Z 2 , Z3 , Z 4 is the same as defined in the first embodiment above, and X is selected from halogen.

[0014] A third aspect of the present invention provides a benzimidazole compound produced by the method according to the second aspect.

[0015] A fourth aspect of the present invention provides the use of a benzimidazole compound or a salt thereof according to the first or third aspect in the manufacture of an insecticide or acaricide.

[0016] A fifth aspect of the present invention provides an insecticide or acaricide containing as an active ingredient at least one kind selected from the benzimidazole compound or a salt thereof according to the first or third aspect described above.

[0017] A sixth aspect of the present invention provides the use of an insecticide or acaricide as defined above in killing insects and / or acaricides in agriculture, forestry and horticulture. Effect of the Invention

[0018] Compared with the prior art, the present invention has at least the following advantages: When the benzimidazole compound or its salt according to the present invention is used as an active ingredient in an insecticide or acaricide, it has an excellent control effect even when used at a low concentration. Other features and advantages of the present invention are described in detail in the Detailed Description section below. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0019] The endpoints of the ranges and any values ​​disclosed herein should be understood not to be limited to the exact ranges or values, but to include values ​​close to these ranges or values. In the case of numerical ranges, the endpoints of each range, and the endpoints and individual point values ​​of each range, and the individual point values ​​between each other, can be combined with each other to obtain one or more new numerical ranges, and these numerical ranges should be considered to be specifically disclosed herein.

[0020] The terms used in the present invention are explained as follows. Halogen refers to fluorine, chlorine, bromine and iodine. Alkyl refers to a linear or branched alkyl group excluding cycloalkyl, and the C1-C8 alkyl refers to an alkyl group having 1 to 8 carbon atoms, including, but not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, n-hexyl, etc.

[0021] Cycloalkyl refers to an alkyl containing a cyclic chain, and the C1-C8 cycloalkyl refers to a cycloalkyl group having 1 to 8 carbon atoms, including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.

[0022] Alkenyl refers to straight or branched chain alkenyl, and the C2-C8 alkenyl refers to alkenyl groups having 2 to 8 carbon atoms, including, but not limited to, 1-propenyl, 2-propenyl, and the various butenyl, pentenyl, and hexenyl isomers, and also includes polyenyls such as 1,2-propadienyl and 2,4-hexadienyl.

[0023] Alkynyl refers to straight-chain or branched-chain alkynyl, and the C2-C8 alkynyl refers to alkynyl groups having 2 to 8 carbon atoms, including, but not limited to, 1-propynyl, 2-propynyl, and the various butynyl, pentynyl, and hexynyl isomers, and further includes groups containing multiple triple bonds, such as 2,5-hexadiynyl.

[0024] Alkoxy refers to a group in which an oxygen atom is linked to the terminal of a straight or branched alkyl group. 1~8 The alkoxy refers to an alkoxy group having 1 to 8 carbon atoms, including, but not limited to, groups such as methoxy, ethoxy, n-propoxy, isopropoxy, and n-butoxy.

[0025] Cycloalkoxy is a group containing an oxygen atom in cycloalkyl, 1~8 The term "cycloalkoxy" refers to a cycloalkoxy group having 1 to 8 carbon atoms, and examples thereof include, but are not limited to, cyclopropoxy, cyclobutoxy, and the like.

[0026] Alkylthio refers to a group in which a sulfur atom is linked to the alkyl terminal end, and examples include, but are not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, t-butylthio, and other groups.

[0027] Alkylsulfinyl refers to a group in which a sulfinyl is linked to the alkyl terminal, and includes, but is not limited to, groups such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, and t-butylsulfinyl.

[0028] Alkylsulfonyl refers to a group in which a sulfonyl is linked to the alkyl terminal, and examples include, but are not limited to, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, t-butylsulfonyl, and other groups.

[0029] Haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, haloalkoxy, halocycloalkoxy, haloalkylthio, haloalkylsulfinyl, and haloalkylsulfonyl respectively refer to a group formed by replacing at least one hydrogen atom of an alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, cycloalkoxy, alkylthio, alkylsulfinyl, or alkylsulfonyl with a halogen atom, and when there are two or more halogen atoms, the halogen atoms may be the same or different.

[0030] 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 refer to alkyl groups in which at least one hydrogen atom is substituted with cycloalkyl, halocycloalkyl, alkoxy, haloalkoxy, cycloalkoxy, or halocycloalkoxy.

[0031] For purposes of the present invention, heteroatoms include, but are not limited to, O, S, and N atoms. Other groups have similar definitions as above, differing only in the number of substituents or carbon atoms, and therefore will not be described in detail. All other terms in the present invention may be explained in a common manner in the art.

[0032] As mentioned above, a first aspect of the present invention provides a benzimidazole compound having a structure represented by formula (I) or a salt thereof:

[0033] [ka]

[0034] (In formula (I), R is a 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, and the optional substituents are each independently selected from halogen, C1-C 10 Alkyl, halo C1-C 10 Alkyl, C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkyl, C1-C 10 Alkoxy, Halo C1~C 10 Alkoxy, C3-C 10 Cycloalkoxy, haloC3~C10 At least one selected from cycloalkoxy; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 are each independently H, halogen, CN, NO2, formyl, or a 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 each set of optional substituents is independently selected from halogen, C1-C6 alkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyl C1-C6 alkyl, substituted or unsubstituted heterocyclyloxy, and each set of optional substituents is independently selected from halogen, C1-C6 alkyl, substituted or unsubstituted aryloxy ... 10 Alkyl, halo C1-C10 Alkyl, C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkyl, C1-C 10 Alkoxy, Halo C1~C 10 Alkoxy, C3-C 10 Cycloalkoxy, haloC3~C 10 cycloalkoxy; and optionally, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 any two adjacent groups among the above are grouped into one pair, and at least one pair is cyclized with the benzene ring to which it is bonded, with or without at least one heteroatom therebetween, to form at least one 3- to 8-membered ring; Z 1 , Z 2 , Z 3 , Z 4 are each independently H, halogen, CN, NO2, formyl, or a 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 10each set of optional substituents is independently selected from halogen, C1-C6 alkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyl C1-C6 alkyl, substituted or unsubstituted heterocyclyloxy, and each set of optional substituents is independently selected from halogen, C1-C6 alkyl, substituted or unsubstituted aryloxy ... 10 Alkyl, halo C1-C 10 Alkyl, C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkyl, C1-C 10 Alkoxy, Halo C1~C 10 Alkoxy, C3-C 10 Cycloalkoxy, haloC3~C 10 cycloalkoxy; and optionally, Z 1 , Z 2 , Z 3 , Z 4 any two adjacent groups among the above are grouped into one pair, and at least one pair is cyclized with the benzene ring to which it is bonded, with or without at least one heteroatom therebetween, to form at least one 3- to 8-membered ring; And Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 3 , Y 4 are all H and R is ethyl, then Y 5 is not H, fluorine or chlorine, but Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 4 , Y5 are all H and R is ethyl, then Y 3 is not fluorine or chlorine, Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 3 , Y 5 are all H and R is ethyl, then Y 2 , Y 4 is not chlorine at the same time.) According to the present invention, the term "optionally" means that a multi-membered ring structure may or may not be present.

[0035] According to the present invention, the Y 1 , Y 2 , Y 3 , Y 4 , Y 5 Any two adjacent groups among Y are grouped into one pair, and at least one pair is cyclized with the benzene ring to which it is bonded, with or without at least one heteroatom therebetween, to form at least one 3- to 8-membered ring, 1 and Y 2 , Y 2 and Y 3 , Y 3 and Y 4 , Y 4 and Y 5 At least one of the combinations of Z forms at least one 3- to 8-membered ring with the benzene ring to which it is bonded, with or without at least one heteroatom. 1 , Z 2 , Z 3 , Z 4 have similar definitions and will not be described in detail here.

[0036] Preferably, in formula (I), R is C1~C 10 Alkyl, halo C1~C 10 Alkyl, C3-C 10 Cycloalkyl substituted C1-C 10 Alkyl, halo C3~C 10 Cycloalkyl substituted C1-C 10 Alkyl, C3-C10 Cycloalkyl substituted halo C1~C 10 Alkyl, C1-C 10 Alkoxy substituted C1-C 10 Alkyl, halo C1~C 10 Alkoxy substituted C1-C 10 Alkyl, C1-C 10 Alkoxy-substituted haloC1-C 10 Alkyl, C3-C 10 Cycloalkoxy substituted C1-C 10 Alkyl, halo C3~C 10 Cycloalkoxy substituted C1-C 10 Alkyl, C3-C 10 Cycloalkoxy substituted halo C1-C 10 Alkyl, C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkyl, C1-C 10 Alkyl substituted C3~C 10 Cycloalkyl, haloC1~C 10 Alkyl substituted C3~C 10 Cycloalkyl, C1-C 10 Alkyl-substituted halo C3~C 10 Cycloalkyl, C1-C 10 Alkoxy substituted C3-C 10 Cycloalkyl, haloC1~C 10 Alkoxy substituted C3-C 10 Cycloalkyl, C1-C 10 Alkoxy-substituted haloC3~C 10 Cycloalkyl, C3-C 10 Cycloalkoxy substituted C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkoxy substituted C3-C 10 Cycloalkyl, C3-C 10 Cycloalkoxy substituted haloC3~C 10 Cycloalkyl, C2-C 10 Alkenyl, HaloC2~C 10 Alkenyl, C2-C 10 Alkynyl, HaloC2~C 10 alkynyl, Y 1 , Y 2 , Y3 , Y 4 , Y 5 are each independently H, halogen, CN, NO2, C1-C 10 Alkyl, halo C1~C 10 Alkyl, C3-C 10 Cycloalkyl substituted C1-C 10 Alkyl, halo C3~C 10 Cycloalkyl substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl substituted halo C1~C 10 Alkyl, C1-C 10 Alkoxy substituted C1-C 10 Alkyl, halo C1~C 10 Alkoxy substituted C1-C 10 Alkyl, C1-C 10 Alkoxy-substituted haloC1-C 10 Alkyl, C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkyl, C1-C 10 Alkyl substituted C3~C 10 Cycloalkyl, haloC1~C 10 Alkyl substituted C3~C 10 Cycloalkyl, C1-C 10 Alkyl-substituted halo C3~C 10 Cycloalkyl, C1-C 10 Alkoxy, Halo C1~C 10 Alkoxy, C1-C 10 Alkylthio, HaloC1~C 10 Alkylthio, C1-C 10 Alkylsulfinyl, HaloC1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, HaloC1-C 10 Alkyl sulfonyl, formyl, C1-C 10 Alkylcarbonyl, HaloC1-C 10 Alkylcarbonyl, C1-C 10 Alkoxycarbonyl, HaloC1-C 10Alkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, halo C2-C6 alkenyloxy, halo C2-C6 alkynyloxy, C1-C 10 Alkylcarbonyloxy, HaloC1~C 10 Alkylcarbonyloxy, C1-C 10 Cyanoalkyl, C1-C 10 Cyanoalkoxy, C1-C 10 each set of optionally present substituents is independently selected from 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, heterocyclyl, heterocyclyl C1-C6 alkyl, and heterocyclyloxy; 10 Alkyl, halo C1~C 10 Alkyl, C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkyl, C1-C 10 Alkoxy, Halo C1~C 10 Alkoxy, C3-C 10 Cycloalkoxy, haloC3~C 10 cycloalkoxy; and optionally, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 any two adjacent groups among the above are grouped into one pair, and at least one pair is cyclized with the benzene ring to which it is bonded, with or without at least one heteroatom therebetween, to form at least one 3- to 8-membered ring; Z 1 , Z 2 , Z 3 , Z 4 are each independently H, halogen, CN, NO2, C1-C 10 Alkyl, halo C1~C10 Alkyl, C3-C 10 Cycloalkyl substituted C1-C 10 Alkyl, halo C3~C 10 Cycloalkyl substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl substituted halo C1~C 10 Alkyl, C1-C 10 Alkoxy substituted C1-C 10 Alkyl, halo C1-C 10 Alkoxy substituted C1-C 10 Alkyl, C1-C 10 Alkoxy-substituted haloC1-C 10 Alkyl, C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkyl, C1-C 10 Alkyl substituted C3~C 10 Cycloalkyl, haloC1~C 10 Alkyl substituted C3~C 10 Cycloalkyl, C1-C 10 Alkyl-substituted halo C3~C 10 Cycloalkyl, C1-C 10 Alkoxy, Halo C1~C 10 Alkoxy, C1-C 10 Alkylthio, HaloC1~C 10 Alkylthio, C1-C 10 Alkylsulfinyl, HaloC1~C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, HaloC1-C 10 Alkyl sulfonyl, formyl, C1-C 10 Alkylcarbonyl, HaloC1~C 10 Alkylcarbonyl, C1-C 10 Alkoxycarbonyl, HaloC1-C 10 Alkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, halo C2-C6 alkenyloxy, halo C2-C6 alkynyloxy, C1-C 10Alkylcarbonyloxy, HaloC1~C 10 Alkylcarbonyloxy, C1-C 10 Cyanoalkyl, C1-C 10 Cyanoalkoxy, C1-C 10 each set of optionally present substituents is independently selected from 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, heterocyclyl, heterocyclyl C1-C6 alkyl, and heterocyclyloxy; 10 Alkyl, halo C1~C 10 Alkyl, C3-C 10 Cycloalkyl, haloC3~C 10 Cycloalkyl, C1-C 10 Alkoxy, Halo C1~C 10 Alkoxy, C3-C 10 Cycloalkoxy, haloC3~C 10 cycloalkoxy; and optionally, Z 1 , Z 2 , Z 3 , Z 4 any two adjacent groups among the above are grouped into one pair, and at least one pair is cyclized with the benzene ring to which it is bonded, with or without at least one heteroatom therebetween, to form at least one 3- to 8-membered ring; And Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 3 , Y 4 are all H and R is ethyl, then Y 5 is not H, fluorine or chlorine, but Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 4 , Y 5are all H and R is ethyl, then Y 3 is not fluorine or chlorine, Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 3 , Y 5 are all H and R is ethyl, then Y 2 , Y 4 is not chlorine at the same time.

[0037] Below, some particularly preferred specific embodiments of the benzimidazole-based compounds of the present invention are provided. Specific embodiment 1 R is C1-C8 alkyl, halo C1-C8 alkyl, C3-C8 cycloalkyl substituted C1-C8 alkyl, halo C3-C8 cycloalkyl substituted C1-C8 alkyl, C3-C8 cycloalkyl substituted halo C1-C8 alkyl, C1-C8 alkoxy substituted C1-C8 alkyl, halo C1-C8 alkoxy substituted C1-C8 alkyl, C1-C8 alkoxy substituted halo C1-C8 alkyl, C3-C8 cycloalkoxy substituted C1-C8 alkyl, halo C3-C8 cycloalkoxy substituted C1-C8 alkyl, C3-C8 cycloalkoxy substituted C1-C8 alkyl, halo C3-C8 cycloalkoxy substituted C1-C8 alkyl, C3-C8 cycloalkoxy substituted halo C1-C8 alkyl, C3-C8 cycloalkyl, halo C3-C8 cycloalkyl, C1-C8 alkyl selected from substituted C3-C8 cycloalkyl, halo C1-C8 alkyl substituted C3-C8 cycloalkyl, C1-C8 alkyl substituted halo C3-C8 cycloalkyl, C1-C8 alkoxy substituted C3-C8 cycloalkyl, halo C1-C8 alkoxy substituted C3-C8 cycloalkyl, C1-C8 alkoxy substituted halo C3-C8 cycloalkyl, C3-C8 cycloalkoxy substituted C3-C8 cycloalkyl, halo C3-C8 cycloalkoxy substituted C3-C8 cycloalkyl, C3-C8 cycloalkoxy substituted halo C3-C8 cycloalkyl, C3-C8 cycloalkoxy substituted halo C3-C8 cycloalkyl, C2-C8 alkenyl, halo C2-C8 alkenyl, C2-C8 alkynyl, halo C2-C8 alkynyl; Y 1 , Y 2 , Y 3 , Y 4 , Y 5are each independently H, halogen, CN, NO2, C1-C8 alkyl, halo C1-C8 alkyl, C3-C8 cycloalkyl substituted C1-C8 alkyl, halo C3-C8 cycloalkyl substituted C1-C8 alkyl, C3-C8 cycloalkyl substituted halo C1-C8 alkyl, C1-C8 alkoxy substituted C1-C8 alkyl, halo C1-C8 alkoxy substituted C1-C8 alkyl, C1-C8 alkoxy substituted halo C1-C8 alkyl, C3-C8 cycloalkyl, halo C3 ~C8 cycloalkyl, C1-C8 alkyl substituted C3-C8 cycloalkyl, halo C1-C8 alkyl substituted C3-C8 cycloalkyl, C1-C8 alkyl substituted halo C3-C8 cycloalkyl, C1-C8 alkoxy, halo C1-C8 alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, C1-C8 alkylsulfinyl, halo C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, and halo C1-C8 alkylsulfonyl; Z 1 , Z 2 , Z 3 , Z 4 are each independently selected from H, halogen, CN, NO2, C1-C8 alkyl, haloC1-C8 alkyl, C3-C8 cycloalkyl, haloC3-C8 cycloalkyl, C1-C8 alkoxy, haloC1-C8 alkoxy, C1-C8 alkylthio, haloC1-C8 alkylthio, C1-C8 alkylsulfinyl, haloC1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, and haloC1-C8 alkylsulfonyl; And Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 3 , Y 4 are all H and R is ethyl, then Y 5 is not H, fluorine or chlorine, but Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 4 , Y 5are all H and R is ethyl, then Y 3 is not fluorine or chlorine, Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 3 , Y 5 are all H and R is ethyl, then Y 2 , Y 4 is not chlorine at the same time.

[0038] Specific embodiment 2 In formula (I), R is selected from C1-C8 alkyl, halo C1-C8 alkyl, C3-C8 cycloalkyl, halo C3-C8 cycloalkyl, C2-C8 alkenyl, halo C2-C8 alkenyl, C2-C8 alkynyl, and halo C2-C8 alkynyl; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 are each independently selected from H, halogen, CN, NO2, C1-C8 alkyl, haloC1-C8 alkyl, C3-C8 cycloalkyl, haloC3-C8 cycloalkyl, C1-C8 alkoxy, haloC1-C8 alkoxy, C1-C8 alkylthio, haloC1-C8 alkylthio, C1-C8 alkylsulfinyl, haloC1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, and haloC1-C8 alkylsulfonyl; Z 1 , Z 2 , Z 3 , Z 4 are each independently selected from H, halogen, CN, NO2, C1-C8 alkyl, haloC1-C8 alkyl, C1-C8 alkoxy, haloC1-C8 alkoxy, C1-C8 alkylthio, haloC1-C8 alkylthio, C1-C8 alkylsulfinyl, haloC1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, and haloC1-C8 alkylsulfonyl; And Z 1 , Z 2 , Z 3 , Z 4, Y 1 , Y 2 , Y 3 , Y 4 are all H and R is ethyl, then Y 5 is not H, fluorine or chlorine, but Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 4 , Y 5 are all H and R is ethyl, then Y 3 is not fluorine or chlorine, Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 3 , Y 5 are all H and R is ethyl, then Y 2 , Y 4 is not chlorine at the same time.

[0039] Specific embodiment 3 In formula (I), R is selected from C1-C8 alkyl, haloC1-C8 alkyl, C3-C8 cycloalkyl, haloC3-C8 cycloalkyl, C2-C5 alkenyl, and C2-C5 alkynyl; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 are each independently selected from H, halogen, CN, NO2, C1-C8 alkyl, haloC1-C8 alkyl, C1-C8 alkoxy, and haloC1-C8 alkoxy; Z 1 , Z 2 , Z 3 , Z 4 are each independently selected from H, halogen, CN, NO2, C1-C8 alkyl, haloC1-C8 alkyl, C1-C8 alkoxy, and haloC1-C8 alkoxy; And Z 1 , Z 2 , Z 3 , Z 4 , Y1 , Y 2 , Y 3 , Y 4 are all H and R is ethyl, then Y 5 is not H, fluorine or chlorine, but Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 4 , Y 5 are all H and R is ethyl, then Y 3 is not fluorine or chlorine, Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 3 , Y 5 are all H and R is ethyl, then Y 2 , Y 4 is not chlorine at the same time.

[0040] Specific embodiment 4 In formula (I), R is selected from methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, allyl, propargyl, and CF; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 are each independently selected from H, F, Cl, Br, I, CN, NO2, CH3, CF3, OCH3, OCF3, OCH2CF3, OCH2CF2CF3, CF2Cl, CFCl2, and CCl3; Z 1 , Z 2 , Z 3 , Z 4 are each independently selected from H, F, Cl, Br, I, CN, NO2, CH3, CF3, OCF3, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, and t-butyl; And Z 1 , Z 2 , Z 3 , Z4 , Y 1 , Y 2 , Y 3 , Y 4 are all H and R is ethyl, then Y 5 is not H, fluorine or chlorine, but Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 4 , Y 5 are all H and R is ethyl, then Y 3 is not fluorine or chlorine, Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 3 , Y 5 are all H and R is ethyl, then Y 2 , Y 4 is not chlorine at the same time.

[0041] Specific embodiment 5 In formula (I), R is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 are each independently selected from H, F, Cl, Br, CN, NO2, OCF3, CH3, CF3, OCH3, OCH2CF3, and OCH2CF2CF3; Z 1 , Z 2 , Z 3 , Z 4 are each independently selected from H, F, Cl, Br, and CH3; And Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 3 , Y 4 are all H and R is ethyl, then Y5 is not H, fluorine or chlorine, but Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 2 , Y 4 , Y 5 are all H and R is ethyl, then Y 3 is not fluorine or chlorine, Z 1 , Z 2 , Z 3 , Z 4 , Y 1 , Y 3 , Y 5 are all H and R is ethyl, then Y 2 , Y 4 is not chlorine at the same time.

[0042] Specific embodiment 6 The benzimidazole compound is at least one selected from the compounds shown in Table 1.

[0043] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7]

[0044] Specific embodiment 7 The benzimidazole compounds include Compound 1-25, Compound 1-26, Compound 1-27, Compound 1-28, Compound 1-29, Compound 1-30, Compound 1-31, Compound 1-32, Compound 1-33, Compound 1-34, Compound 1-37, Compound 1-38, Compound 1-40, Compound 1-43, Compound 1-47, Compound 1-49, Compound 1-50, Compound 1-51, Compound 1-52, Compound 1-54, Compound 1-55, Compound 1-56, Compound 1-57, Compound 1-60, Compound Compound 1-61, Compound 1-62, Compound 1-68, Compound 1-69, Compound 1-72, Compound 1-73, Compound 1-75, Compound 1-76, Compound 1-81, Compound 1-133, Compound 1-174, Compound 1-186, Compound 1-213, Compound 1-214, Compound 1-218, Compound 1-235, Compound 1-239, Compound 1-254, Compound 1-255, Compound 1-257, Compound 1-261, Compound 1-264, and Compound 1-265.

[0045] Specific embodiment 8 The benzimidazole compound is at least one selected from Compound 1-26, Compound 1-27, Compound 1-28, Compound 1-29, Compound 1-30, Compound 1-31, Compound 1-32, Compound 1-34, Compound 1-37, Compound 1-38, Compound 1-47, Compound 1-49, Compound 1-56, Compound 1-57, Compound 1-61, Compound 1-68, Compound 1-69, Compound 1-73, Compound 1-133, Compound 1-174, Compound 1-186, Compound 1-213, Compound 1-214, Compound 1-218, Compound 1-235, Compound 1-239, Compound 1-254, Compound 1-255, Compound 1-257, Compound 1-261, Compound 1-264, and Compound 1-265.

[0046] Specific embodiment 9 The benzimidazole compound is at least one selected from Compound 1-27, Compound 1-28, Compound 1-47, Compound 1-56, Compound 1-57, Compound 1-133, Compound 1-174, Compound 1-186, Compound 1-213, Compound 1-214, Compound 1-218, Compound 1-235, Compound 1-239, Compound 1-254, Compound 1-255, Compound 1-257, Compound 1-261, Compound 1-264, and Compound 1-265.

[0047] The inventors of the present invention have found that the benzimidazole compounds or salts thereof in the multiple preferred specific embodiments provided above have superior insecticidal and acaricidal effects, and that the benzimidazole compounds or salts thereof in particularly preferred specific embodiments 7 to 9, and the even more preferred compound of specific embodiment 9, have superior insecticidal and acaricidal effects, and even when used at a low concentration (e.g., 6.25 mg / L), they have superior insecticidal and acaricidal effects. Furthermore, the performance data (nuclear magnetism) of some compounds of the present invention are shown in Table 2.

[0048] [Table 2-1] [Table 2-2] [Table 2-3] [Table 2-4] [Table 2-5]

[0049] In the present invention, the salt in the benzimidazole compound or a salt thereof includes inorganic salts such as hydrochloride, sulfate, nitrate, phosphate, etc.; and organic salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate, etc.

[0050] As stated above, the second aspect of the present invention is (1) performing a first reaction between compound V and compound IV in a first solvent in the presence of a first alkaline substance and a condensing agent to obtain compound III; (2) performing a second reaction between the compound III and an acidic substance in a second solvent to obtain a compound II; and (3) performing a third reaction of compound II with a sulfonyl-containing compound in a third solvent in the presence of a second alkaline material to obtain the benzimidazole compound, The present invention provides a method for preparing a benzimidazole compound, wherein compound V has a structure represented by formula (V), compound IV has a structure represented by formula (IV), compound III has a structure represented by formula (III), compound II has a structure represented by formula (II), the benzimidazole compound has a structure represented by formula (I), and the sulfonyl-containing compound has a structure represented by formula (VI).

[0051] [ka]

[0052] (In the formula (I), formula (II), formula (III), formula (IV), formula (V), and formula (VI), R, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Z 1 , Z 2 , Z 3 , Z 4 is the same as defined above in the first embodiment, and X is selected from halogen.

[0053] According to the present invention, in step (1), the first reaction is as follows:

[0054] [ka]

[0055] Preferably, in step (1), the first reaction conditions include a temperature of from −10° C. to 150° C. and a reaction time of from 0.5 to 48 hours. Preferably, in step (1), the molar ratio of the amounts of the compound V and the compound IV used is 0.5 to 2: 1. The compound V and the compound IV are commercially available.

[0056] Preferably, in step (1), the condensing agent is at least one selected from 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or its hydrochloride (EDCI), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), diethyl cyanophosphate (DEPC), a chlorocarbonate compound, and 2-chloro-1-methylpyridinium iodide. Preferably, in step (1), the molar ratio of the amount of the condensing agent to the amount of the compound IV used is 1-2:1.

[0057] Preferably, in step (1), the first alkaline substance is at least one selected from 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 t-butoxide, potassium t-butoxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene. Preferably, in step (1), the molar ratio of the amount of the first alkaline substance to the amount of the compound IV used is 0.1-10:1.

[0058] Preferably, in step (1), the first solvent is at least one selected from pyridine, dichloromethane, chloroform, carbon tetrachloride, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, ethyl ether, methyl t-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. Preferably, in step (1), the amount of the first solvent used is 1 to 20 mL relative to 1 mmol of the compound IV.

[0059] According to the present invention, in step (1), the first solvent and the first alkaline substance may be the same, for example, both may be pyridine. If the first solvent and the first alkaline substance are the same substance, both need to be weighed separately. According to the present invention, in step (2), the second reaction is as follows:

[0060] [ka]

[0061] Preferably, in step (2), the second reaction conditions include a temperature of from -10°C to 300°C and a reaction time of from 0.5 to 48 hours. Preferably, in step (2), the acidic substance is at least one selected from 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.

[0062] Preferably, in step (2), the molar ratio of the amount of the acidic substance to the amount of the compound IV used is 0.01-10:1. Preferably, in step (2), the second solvent is at least one selected from N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA), N-methylpyrrolidone (NMP), ethyl ether, methyl t-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.

[0063] Preferably, in step (2), the amount of the second solvent used is 1 to 20 mL relative to 1 mmol of the compound III. Preferably, step (2) further comprises adjusting the pH value of the system to 7-10 with an alkaline solution after the second reaction, the alkaline solution being, for example, an aqueous sodium hydroxide solution. According to the present invention, in step (3), the third reaction is as follows:

[0064] [ka]

[0065] Preferably, in step (3), the third reaction conditions include a temperature of from -10°C to 100°C and a reaction time of from 0.5 to 48 hours. Preferably, in step (3), the molar ratio of the amount of the sulfonyl-containing compound to the amount of compound II used is 0.8-10:1. Preferably, in step (3), the sulfonyl-containing compound is at least one selected from methylsulfonyl chloride, ethylsulfonyl chloride, n-propylsulfonyl chloride, and n-butylsulfonyl chloride, more preferably ethylsulfonyl chloride.

[0066] Preferably, in step (3), the second alkaline substance is at least one selected from 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 t-butoxide, potassium t-butoxide, and 1,8-diazabicyclo[5.4.0]undec-7-ene. Preferably, in step (3), the molar ratio of the amount of the second alkaline substance to the amount of the compound II used is 1-10:1.

[0067] Preferably, in step (3), the third solvent is at least one selected from ethyl 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. Preferably, in step (3), the amount of the third solvent used is 1 to 20 mL relative to 1 mmol of the compound II.

[0068] According to a preferred specific embodiment of the present invention, step (3) includes first carrying out a first-stage third reaction with compound II in a third solvent and in the presence of a second alkaline substance, and then adding the sulfonyl-containing compound to carry out a second-stage third reaction to obtain the benzimidazole compound. Preferably, the conditions for the first-stage third reaction include a temperature of −10° C. to 100° C. and a reaction time of 10 to 120 minutes. Preferably, the conditions for the second-stage third reaction include a temperature of -10°C to 100°C and a reaction time of 0.5 to 48 hours.

[0069] According to the present invention, the method may further include various post-treatment operation means conventionally used in the art, such as extraction, washing, drying, suction filtration, concentration, and separation and purification. The present invention is not particularly limited thereto, and the method may be carried out using various conventional operations in the art, for example, ethyl acetate is used for extraction, anhydrous sodium sulfate is used for drying, vacuum concentration is used for concentration, and column chromatography is used for separation and purification.

[0070] As mentioned above, the third aspect of the present invention provides a benzimidazole compound prepared by the method according to the second aspect. As described above, a fourth aspect of the present invention provides use of a benzimidazole compound or a salt thereof according to the first or third aspect in the manufacture of an insecticide or acaricide. Preferably, the benzimidazole compound or a salt thereof is used as an active ingredient (ie, effective ingredient) in the insecticide or acaricide.

[0071] As described above, the fifth aspect of the present invention provides an insecticide or acaricide containing an active ingredient which is at least one selected from the benzimidazole compounds or salts thereof described in the first or third aspect. In the fifth aspect of the present invention, the content of the active ingredient is preferably 1 to 99% by weight, for example, 1% by weight, 5% by weight, 10% by weight, 15% by weight, 20% by weight, 25% by weight, 30% by weight, 35% by weight, 40% by weight, 45% by weight, 50% by weight, 55% by weight, 60% by weight, 65% by weight, 70% by weight, 75% by weight, 80% by weight, 85% by weight, 90% by weight, 95% by weight, 99% by weight, and any value within a range consisting of any two of these point values. More preferably, the content of the active ingredient is 5 to 60% by weight, based on the total weight of the insecticide or acaricide.

[0072] In the fifth aspect of the present invention, the insecticide / acaricide preferably further contains a carrier. Preferably, the carrier of the insecticide / acaricide is a material acceptable for agriculture, forestry and horticulture and advantageous for application of the active ingredient. Particularly preferably, the carrier is a liquid carrier and / or a solid carrier, the solid carrier being preferably at least one solid material selected from clay, natural or synthetic silicate, silica, resin, wax, solid fertilizer, and the liquid carrier being preferably a liquid material selected from water, alcohols, ketones, petroleum fractions, aromatic compounds, chlorinated hydrocarbons, and liquefied petroleum gas.

[0073] In the fifth aspect of the present invention, the insecticide and acaricide may include surfactants, protective colloids, adhesives, thickeners, thixotropic agents, penetrating agents, chelating agents, colorants, polymers, and other auxiliary components commonly used in this field, which are not particularly limited in the present invention. Those skilled in the art can select a reasonable composition and amount of use according to actual needs.

[0074] In the fifth aspect of the present invention, preferably, the formulation of the insecticide / acaricide is independently at least one selected from wettable powders, soluble powders, emulsifiable oil agents, aqueous suspensions, dispersible oil suspensions, aqueous emulsions, suspensible emulsions, microemulsions, aqueous preparations, granules, microcapsules, and water-dispersible granules, thereby making the active ingredient more soluble or dispersible and more dispersible when used as an active substance of the insecticide or acaricide, thereby enhancing the application effect. In the fifth aspect of the present invention, the present invention does not particularly limit the method for producing the insecticide / acaricide, and a person skilled in the art can obtain a reagent having a desired composition and formulation by producing the insecticide / acaricide using a method described in conventional literature or standards in the field or a conventional method in the field.

[0075] As mentioned above, a sixth aspect of the present invention provides the use of an insecticide or acaricide as described above in killing insects and / or acaricides in agriculture, forestry and horticulture. Preferably, the method of use comprises applying the insecticide to pests and / or mites or applying the insecticide to a medium in which pests and / or mites live. According to the invention, the medium in which pests live is, for example, a plant or soil.

[0076] Preferably, the effective amount of application (i.e., the amount of active ingredient used) is 10 g to 1000 g per hectare of soil, more preferably 20 g to 500 g per hectare of soil. According to the present invention, the specific method of application is not particularly limited and may be carried out by a conventional method in the art, for example, spraying the insecticide / acaricide on pests and / or mites, or on the living medium of pests and / or mites.

[0077] According to the present invention, in the use of said insecticide / acaricide in killing insects and / or acars in agriculture, forestry and horticulture, said insecticide / acaricide may be applied in combination with conventional substances such as fungicides, insecticides, herbicides, plant growth regulators, plant fertilizers and the like in the relevant field, and such combination produces additive or synergistic effects to obtain better effects. The present invention is not particularly limited thereto, and when the benzimidazole compound or its salt of the present invention is contained as an active ingredient, those skilled in the art may use the benzimidazole compound or its salt in a reasonable combination with an appropriate amount of substance according to actual needs.

[0078] The present invention will now be described in detail with reference to the following examples. In the following examples, all raw materials used are commercially available unless otherwise stated. The origins of some of the raw materials are shown in Table 3.

[0079] [Table 3]

[0080] In the following examples, unless otherwise specified, room temperature refers to 25±2°C. Example 1 Preparation of Compounds 1-27

[0081] [ka]

[0082] The specific manufacturing process is as follows. (1) The first solvent (pyridine, 15 mL), condensing agent (EDCI, 15 mmol), first alkaline substance (DMAP, 2 mmol), compound V (V-1, 10 mmol) and compound IV (IV-1, 10 mmol) were added to a reaction flask and reacted at room temperature for 3 hours to carry out the first reaction. After that, water and ethyl acetate were added for extraction, the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, suction filtered, and the filtrate was concentrated under reduced pressure to obtain compound III.

[0083] (2) The obtained compound III was dissolved in a second solvent (NMP, 15 mL), and an acidic substance (p-toluenesulfonic acid monohydrate, 30 mmol) was added and reacted at 160° C. for 4 hours to carry out the second reaction. The mixture was cooled to room temperature, and a 10 wt% aqueous sodium hydroxide solution was added to adjust the pH value of the system to 9. The mixture was then extracted with ethyl acetate, and the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, filtered by suction, and the filtrate was concentrated under reduced pressure to obtain compound II (II-1, 8 mmol).

[0084] (3) The compound II was dissolved in a third solvent (THF, 30 mL), and a second alkaline substance (NaH coated with 0.96 g of mineral oil, NaH content 60 wt%, NaH 24 mmol) was added. After reacting at room temperature for 10 min, a sulfonyl-containing compound (ethylsulfonyl chloride, 24 mmol) was added and reacted at room temperature for 12 h. The mixture was quenched by adding saturated ammonium chloride, extracted with ethyl acetate, the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, suction filtered, the filtrate was concentrated under reduced pressure, and the obtained product was separated and purified by column chromatography to obtain compound 1-27 (2.08 g).

[0085] Example 2 Preparation of Compound 1-28

[0086] [ka]

[0087] The specific manufacturing process is as follows. (1) The first solvent (pyridine, 15 mL), condensing agent (EDCI, 15 mmol), first alkaline substance (DMAP, 2 mmol), compound V (V-1, 10 mmol) and compound IV (IV-2, 10 mmol) were added to a reaction flask and reacted at room temperature for 3 hours to carry out the first reaction. After that, water and ethyl acetate were added for extraction, the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, suction filtered, and the filtrate was concentrated under reduced pressure to obtain compound III.

[0088] (2) The obtained compound III was dissolved in a second solvent (NMP, 15 mL), and an acidic substance (p-toluenesulfonic acid monohydrate, 30 mmol) was added and reacted at 160° C. for 4 hours to carry out the second reaction. The mixture was cooled to room temperature, and a 10 wt% aqueous sodium hydroxide solution was added to adjust the pH value of the system to 10. The mixture was then extracted with ethyl acetate, and the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, filtered by suction, and the filtrate was concentrated under reduced pressure to obtain compound II (II-2, 8.2 mmol).

[0089] (3) The compound II was dissolved in a third solvent (THF, 30 mL), a second alkaline substance (NaH coated with 0.98 g of mineral oil, NaH content 60 wt%, NaH 24.6 mmol) was added, and the mixture was reacted at room temperature for 10 min., after which a sulfonyl-containing compound (ethylsulfonyl chloride, 24.6 mmol) was added and reacted at room temperature for 12 h. After the reaction, the mixture was quenched by adding saturated ammonium chloride, extracted with ethyl acetate, the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, suction filtered, the filtrate was concentrated under reduced pressure, and the obtained product was separated and purified by column chromatography to obtain compound 1-28 (2.10 g).

[0090] Example 3 Preparation of Compound 1-47

[0091] [ka]

[0092] The specific manufacturing process is as follows. (1) The first solvent (pyridine, 15 mL), condensing agent (EDCI, 15 mmol), first alkaline substance (DMAP, 2 mmol), compound V (formula V-1, 10 mmol) and chemical substance IV (IV-3, 10 mmol) were added to a reaction flask and reacted at room temperature for 3 h to carry out the first reaction. After that, water and ethyl acetate were added for extraction, the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, suction filtered, and the filtrate was concentrated under reduced pressure to obtain compound III.

[0093] (2) The obtained compound III was dissolved in a second solvent (NMP, 15 mL), and an acidic substance (p-toluenesulfonic acid monohydrate, 30 mmol) was added and reacted at 160° C. for 4 hours to carry out the second reaction. The mixture was cooled to room temperature, and a 10 wt% aqueous sodium hydroxide solution was added to adjust the pH value of the system to 10. The mixture was then extracted with ethyl acetate, and the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, filtered by suction, and the filtrate was concentrated under reduced pressure to obtain compound II (II-3, 8 mmol).

[0094] (3) The compound II was dissolved in a third solvent (THF, 30 mL), and a second alkaline substance (NaH coated with 0.96 g of mineral oil, NaH content 60 wt%, NaH 24 mmol) was added. After reacting at room temperature for 10 min, a sulfonyl-containing compound (ethylsulfonyl chloride, 24 mmol) was added and reacted at room temperature for 12 h. After the reaction, the reaction was quenched by adding saturated ammonium chloride, extracted with ethyl acetate, and the organic phase was washed with saturated saline and dried over anhydrous sodium sulfate. The reaction was filtered by suction, and the filtrate was concentrated under reduced pressure. The obtained product was separated and purified by column chromatography to obtain compound formula 1-47 (2.53 g).

[0095] Example 4 Preparation of Compound 1-56

[0096] [ka]

[0097] The specific manufacturing process is as follows. (1) The first solvent (pyridine, 15 mL), condensing agent (EDCI, 15 mmol), first alkaline substance (DMAP, 2 mmol), compound V (V-2, 10 mmol) and compound IV (IV-1, 10 mmol) were added to a reaction flask and reacted at room temperature for 3 hours to carry out the first reaction. After that, water and ethyl acetate were added for extraction, the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, suction filtered, and the filtrate was concentrated under reduced pressure to obtain compound III.

[0098] (2) The obtained compound III was dissolved in a second solvent (NMP, 15 mL), and an acidic substance (p-toluenesulfonic acid monohydrate, 30 mmol) was added and reacted at 160° C. for 4 hours to carry out the second reaction. The mixture was cooled to room temperature, and a 10 wt% aqueous sodium hydroxide solution was added to adjust the pH value of the system to 10. The mixture was then extracted with ethyl acetate, and the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, filtered by suction, and the filtrate was concentrated under reduced pressure to obtain compound II (II-4, 7.5 mmol).

[0099] (3) The compound II was dissolved in a third solvent (THF, 30 mL), a second alkaline substance (NaH coated with 0.90 g of mineral oil, NaH content 60 wt%, 22.5 mmol) was added, and the mixture was reacted at room temperature for 10 min., after which a sulfonyl-containing compound (ethylsulfonyl chloride, 22.5 mmol) was added and the mixture was reacted at room temperature for another 12 h. After the reaction, the mixture was quenched by adding saturated ammonium chloride, extracted with ethyl acetate, the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, suction filtered, the filtrate was concentrated under reduced pressure, and the obtained product was separated and purified by column chromatography to obtain the compound 1-56 (2.16 g).

[0100] Example 5 Preparation of Compound 1-57

[0101] [ka]

[0102] The specific manufacturing process is as follows. (1) The first solvent (pyridine 15 mL), condensing agent (EDCI, 15 mmol), first alkaline substance (DMAP, 2 mmol), compound V (V-2, 10 mmol) and compound IV (IV-2, 10 mmol) were added to a reaction flask and reacted at room temperature for 3 hours to carry out the first reaction. Extraction was performed by adding water and ethyl acetate, and the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, suction filtered, and the filtrate was concentrated under reduced pressure to obtain compound III.

[0103] (2) The obtained compound III was dissolved in a second solvent (NMP, 15 mL), and an acidic substance (p-toluenesulfonic acid monohydrate, 30 mmol) was added and reacted at 160° C. for 4 hours to carry out the second reaction. The mixture was cooled to room temperature, and a 10 wt% aqueous sodium hydroxide solution was added to adjust the pH value of the system to 9. The mixture was then extracted with ethyl acetate, and the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, filtered by suction, and the filtrate was concentrated under reduced pressure to obtain compound II (II-5, 7.23 mmol).

[0104] (3) The compound II was dissolved in a third solvent (THF, 30 mL), and a second alkaline substance (NaH coated with 0.86 g of mineral oil, NaH content 60 wt%, NaH 21.6 mmol) was added. After reacting at room temperature for 10 min, a sulfonyl-containing compound (ethylsulfonyl chloride, 21.6 mmol) was added and reacted at room temperature for another 12 h. After the reaction, the mixture was quenched by adding saturated ammonium chloride, extracted with ethyl acetate, the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, suction filtered, the filtrate was concentrated under reduced pressure, and the obtained product was separated and purified by column chromatography to obtain compound formula 1-57 (2.12 g).

[0105] Example 6 Preparation of Compound 1-213

[0106] [ka]

[0107] The specific manufacturing process is as follows. (1) The first solvent (pyridine, 15 mL), condensing agent (EDCI, 15 mmol), first alkaline substance (DMAP, 2 mmol), compound V (V-1, 10 mmol) and compound IV (IV-4, 10 mmol) were added to a reaction flask and reacted at room temperature for 3 hours to carry out the first reaction. After that, water and ethyl acetate were added for extraction, the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, suction filtered, and the filtrate was concentrated under reduced pressure to obtain compound III.

[0108] (2) The obtained compound III was dissolved in a second solvent (NMP, 15 mL), and an acidic substance (p-toluenesulfonic acid monohydrate, 30 mmol) was added and reacted at 160° C. for 4 hours to carry out the second reaction. The mixture was cooled to room temperature, and a 10 wt% aqueous sodium hydroxide solution was added to adjust the pH value of the system to 10. The mixture was then extracted with ethyl acetate, and the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, filtered by suction, and the filtrate was concentrated under reduced pressure to obtain compound II (II-6, 8.2 mmol).

[0109] (3) The compound II was dissolved in a third solvent (THF, 30 mL), a second alkaline substance (NaH coated with 0.98 g of mineral oil, NaH content 60 wt%, NaH 24.6 mmol) was added, and the mixture was reacted at room temperature for 10 min., after which a sulfonyl-containing compound (ethylsulfonyl chloride, 24.6 mmol) was added and reacted at room temperature for 12 h. After the reaction, the mixture was quenched by adding saturated ammonium chloride, extracted with ethyl acetate, the organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, suction filtered, the filtrate was concentrated under reduced pressure, and the obtained product was separated and purified by column chromatography to obtain compound 1-213 (2.10 g).

[0110] Remaining Examples The following compounds were prepared in a manner similar to that of Example 1. Except for the types and / or amounts of raw materials used, the rest was the same as that of Example 1. Compound 1-25, Compound 1-26, Compound 1-29, Compound 1-30, Compound 1-31, Compound 1-32, Compound 1-33, Compound 1-34, Compound 1-37, Compound 1-38, Compound 1-40, Compound 1-43, Compound 1-49, Compound 1-50, Compound 1-51, Compound 1-52, Compound 1-54, Compound 1-55, Compound Compounds 1-60, 1-61, 1-62, 1-68, 1-69, 1-72, 1-73, 1-75, 1-76, 1-81, 1-133, 1-174, 1-186, 1-214, 1-218, 1-235, 1-239, 1-254, 1-255, 1-257, 1-261, 1-264, and 1-265 were obtained, respectively.

[0111] Biological activity testing In this test example, the acaricidal activity of the compound prepared above, specifically the acaricidal activity against Tetranychus cinnabarinus, is tested, and the specific test process is as follows: (1) The compound to be measured was dissolved in acetone, and then diluted with a 0.1 wt% aqueous solution of Twain 80 to the desired concentration (see Test Examples 1-A to 1-D below for details) to produce a drug with an acetone content of 5 wt% or less.

[0112] (2) One true leaf was removed from each of the bean seedlings that had grown to two true leaves, and the number of inoculated mites was counted 24 hours after inoculation with Tetranychus cinnabarinus (the number of Tetranychus cinnabarinus inoculated per bean seedling was 50-150). The pesticide prepared in (1) was sprayed onto each of the three bean seedlings using a hand-held sprayer (amount sprayed per seedling was 0.5 mL), and the seedlings were observed in a thermostatic observation room (25°C). After 72 hours, the number of surviving mites was counted, and the mortality rate was calculated. Mortality rate (%) = (number of inoculated mites - number of live mites after spraying) / number of inoculated mites x 100

[0113] Test Example 1-A The compounds were diluted to a concentration of 100 mg / L and then tested as above, in which the following compounds showed a mortality rate of over 90% at a concentration of 100 mg / L, and the specific results are shown in Table 4. Compound 1-25, Compound 1-26, Compound 1-27, Compound 1-28, Compound 1-29, Compound 1-30, Compound 1-31, Compound 1-32, Compound 1-33, Compound 1-34, Compound 1-37, Compound 1-38, Chemical Compound 1-40, Compound 1-43, Compound 1-47, Compound 1-49, Compound 1-50, Compound 1-51, Compound 1-52, Compound 1-54, Compound 1-55, Compound 1-56, Compound 1-57, Compound 1-60, Compound 1-61, Compound 1-62, Compound 1-68, Compound 1-69, Compound 1-72, Compound 1-73, Compound 1-75, Compound 1-76, Compound 1-81, Compound 1-133, Compound 1-174, Compound 1-186, Chemical Compound 1-213, Compound 1-214, Compound 1-218, Compound 1-235, Compound 1-239, Compound 1-254, Compound 1-255, Compound 1-257, Compound 1-261, Compound 1-264, Compound 1-265.

[0114] Test Example 1-B The compounds were diluted to a concentration of 25 mg / L and then tested as above, in which the following compounds showed a mortality rate of over 90% at a concentration of 25 mg / L, and the specific results are shown in Table 4. Compound 1-26, Compound 1-27, Compound 1-28, Compound 1-29, Compound 1-30, Compound 1-31, Compound 1-32, Compound 1-34, Compound 1-37, compound 1-38, compound 1-47, compound 1-49, compound 1-56, compound 1-57, compound 1-61, compound 1-68, compound 1-69 , compound 1-73, compound 1-133, compound 1-174, compound 1-186, compound 1-213, compound 1-214, compound 1-218, compound 1 -235, compound 1-239, compound 1-254, compound 1-255, compound 1-257, compound 1-261, compound 1-264, compound 1-265.

[0115] Test Example 1-C The compounds were diluted to a concentration of 6.25 mg / L and then tested as above, in which the following compounds showed a mortality rate of over 90% at 6.25 mg / L, and the specific results are shown in Table 4. Compound 1-27, Compound 1-28, Compound 1-47, Compound 1-56, Compound 1-57, Compound 1-133, Compound 1-174, Compound 1-186, Compound 1-213, Compound 1-21 4, Compound 1-218, Compound 1-235, Compound 1-239, Compound 1-254, Compound 1-255, Compound 1-257, Compound 1-261, Compound 1-264, Compound 1-265.

[0116] [Table 4]

[0117] Comparative test example In the present invention, the biological activities of the following compounds against Tetranychus cinnabarinus were also tested as above, and the test results are shown in Table 5 below.

[0118] [ka]

[0119] [Table 5]

[0120] As can be seen from the above test results, the benzimidazole compound or its salt according to the present invention has excellent insecticidal and acaricidal effects, and its insecticidal and acaricidal activity is much higher than that of known compounds. In particular, when the benzimidazole compound of the present invention is used at a low concentration (e.g., 6.25 mg / L), it shows excellent insecticidal and acaricidal effects.

[0121] Although the preferred embodiments of the present invention have been described in detail above, the present invention is not limited thereto. Various modifications can be made to the technical solutions of the present invention, including combining each technical feature in any suitable manner, without departing from the technical concept of the present invention, and these simple modifications and combinations should also be regarded as the disclosure of the present invention, and all are within the patent scope of the present invention.

Claims

1. An insecticide / acaricide characterized by comprising at least one active ingredient selected from benzimidazole compounds having the structure represented by formula (I) or salts thereof. 【Chemistry 1】 (In formula (I), R is a substituted or unsubstituted C ２ ~C １０ Alkyl, substituted or unsubstituted C ３ ~C １０ Cycloalkyl, substituted or unsubstituted C ２ ~C １０ Alkenyl, substituted or unsubstituted C ２ ~C １０ alkynyl, and the optional substituents are each independently selected from halogen, C １ ~C １０ Alkyl, haloC １ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl, haloC ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkoxy, HaloC １ ~C １０ Alkoxy, C ３ ~C １０ Cycloalkoxy, haloC ３ ~C １０ At least one selected from cycloalkoxy; Y １ , Y ２ , Y ３ , Y ４ , Y ５ are each independently H, halogen, CN, or NO ２ , formyl, substituted or unsubstituted C １ ~C １０ Alkyl, substituted or unsubstituted C ３ ~C １０ Cycloalkyl, substituted or unsubstituted C １ ~C １０ Alkoxy, substituted or unsubstituted C １ ~C １０ Alkylthio, substituted or unsubstituted C １ ~C １０ Alkylsulfinyl, substituted or unsubstituted C １ ~C １０ Alkylsulfonyl, substituted or unsubstituted C １ ~C １０ Alkylcarbonyl, substituted or unsubstituted C １ ~C １０ Alkoxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C ２ ~C ６ Alkenyl, substituted or unsubstituted C ２ ~C ６ Alkynyl, substituted or unsubstituted C ２ ~C ６ Alkenyloxy, substituted or unsubstituted C ２ ~C ６ Alkynyloxy, substituted or unsubstituted C １ ~C １０ Alkylcarbonyloxy, substituted or unsubstituted C １ ~C １０ Cyanoalkyl, substituted or unsubstituted C １ ~C １０ Cyanoalkoxy, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryl C １ ~C ６ Alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C １ ~C ６ Alkoxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylthio, substituted or unsubstituted arylC １ ~C ６ Alkylsulfonyl, substituted or unsubstituted aryl C １ ~C ６ Alkyl sulfinyl, substituted or unsubstituted aryl C １ ~C ６ Alkylthio, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyl C １ ~C ６ each set of optional substituents is independently selected from halogen, C １ ~C １０ Alkyl, haloC １ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl, haloC ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkoxy, HaloC １ ~C １０ Alkoxy, C ３ ~C １０ Cycloalkoxy, haloC ３ ~C １０ cycloalkoxy; and optionally, Y １ , Y ２ , Y ３ , Y ４ , Y ５ Any two adjacent groups among the above are grouped into a pair, and at least one pair is cyclized with the benzene ring to which it is bonded, with or without at least one heteroatom therebetween, to form at least one 3- to 8-membered ring; Z １ , Z ２ , Z ３ , Z ４ are each independently H, halogen, CN, or NO ２ , formyl, substituted or unsubstituted C １ ~C １０ Alkyl, substituted or unsubstituted C ３ ~C １０ Cycloalkyl, substituted or unsubstituted C １ ~C １０ Alkoxy, substituted or unsubstituted C １ ~C １０ Alkylthio, substituted or unsubstituted C １ ~C １０ Alkylsulfinyl, substituted or unsubstituted C １ ~C １０ Alkylsulfonyl, substituted or unsubstituted C １ ~C １０ Alkylcarbonyl, substituted or unsubstituted C １ ~C １０ Alkoxycarbonyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxycarbonyl, substituted or unsubstituted C ２ ~C ６ Alkenyl, substituted or unsubstituted C ２ ~C ６ Alkynyl, substituted or unsubstituted C ２ ~C ６ Alkenyloxy, substituted or unsubstituted C ２ ~C ６ Alkynyloxy, substituted or unsubstituted C １ ~C １０ Alkylcarbonyloxy, substituted or unsubstituted C １ ~C １０ Cyanoalkyl, substituted or unsubstituted C １ ~C １０ Cyanoalkoxy, substituted or unsubstituted silyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted aryl C １ ~C ６ Alkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl C １ ~C ６ Alkoxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted arylsulfinyl, substituted or unsubstituted arylthio, substituted or unsubstituted arylC １ ~C ６ Alkylsulfonyl, substituted or unsubstituted aryl C １ ~C ６ Alkyl sulfinyl, substituted or unsubstituted aryl C １ ~C ６ Alkylthio, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyl C １ ~C ６ each set of optional substituents is independently selected from halogen, C １ ~C １０ Alkyl, haloC １ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl, haloC ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkoxy, HaloC １ ~C １０ Alkoxy, C ３ ~C １０ Cycloalkoxy, haloC ３ ~C １０ cycloalkoxy; and optionally, Z １ , Z ２ , Z ３ , Z ４ Any two adjacent groups among the above are grouped into a pair, and at least one pair is cyclized with the benzene ring to which it is bonded, with or without at least one heteroatom therebetween, to form at least one 3- to 8-membered ring; And Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ２ , Y ３ , Y ４ are all H and R is ethyl, then Y ５ is not H, fluorine or chlorine, but Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ２ , Y ４ , Y ５ are all H and R is ethyl, then Y ３ is not fluorine or chlorine, Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ３ , Y ５ are all H and R is ethyl, then Y ２ , Y ４ is not chlorine at the same time.)

2. In the formula (I), R is C ２ ~C １０ Alkyl, haloC ２ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl-substituted C ２ ~C １０ Alkyl, haloC ３ ~C １０ Cycloalkyl-substituted C ２ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl-substituted haloC ２ ~C １０ Alkyl, C １ ~C １０ Alkoxy-substituted C ２ ~C １０ Alkyl, haloC １ ~C １０ Alkoxy-substituted C ２ ~C １０ Alkyl, C １ ~C １０ Alkoxy-substituted haloC ２ ~C １０ Alkyl, C ３ ~C １０ Cycloalkoxy-substituted C ２ ~C １０ Alkyl, haloC ３ ~C １０ Cycloalkoxy-substituted C ２ ~C １０ Alkyl, C ３ ~C １０ Cycloalkoxy-substituted halo C ２ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl, haloC ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkyl-substituted C ３ ~C １０ Cycloalkyl, haloC １ ~C １０ Alkyl-substituted C ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkyl-substituted haloC ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkoxy-substituted C ３ ~C １０ Cycloalkyl, haloC １ ~C １０ Alkoxy-substituted C ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkoxy-substituted haloC ３ ~C １０ Cycloalkyl, C ３ ~C １０ Cycloalkoxy-substituted C ３ ~C １０ Cycloalkyl, haloC ３ ~C １０ Cycloalkoxy-substituted C ３ ~C １０ Cycloalkyl, C ３ ~C １０ Cycloalkoxy-substituted halo C ３ ~C １０ Cycloalkyl, C ２ ~C １０ Alkenyl, HaloC ２ ~C １０ Alkenyl, C ２ ~C １０ Alkynyl, HaloC ２ ~C １０ alkynyl, Y １ , Y ２ , Y ３ , Y ４ , Y ５ are each independently H, halogen, CN, or NO ２ , C １ ~C １０ Alkyl, haloC １ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl-substituted C １ ~C １０ Alkyl, haloC ３ ~C １０ Cycloalkyl-substituted C １ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl-substituted haloC １ ~C １０ Alkyl, C １ ~C １０ Alkoxy-substituted C １ ~C １０ Alkyl, haloC １ ~C １０ Alkoxy-substituted C １ ~C １０ Alkyl, C １ ~C １０ Alkoxy-substituted haloC １ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl, haloC ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkyl-substituted C ３ ~C １０ Cycloalkyl, haloC １ ~C １０ Alkyl-substituted C ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkyl-substituted haloC ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkoxy, HaloC １ ~C １０ Alkoxy, C １ ~C １０ Alkylthio, HaloC １ ~C １０ Alkylthio, C １ ~C １０ Alkylsulfinyl, HaloC １ ~C １０ Alkylsulfinyl, C １ ~C １０ Alkylsulfonyl, HaloC １ ~C １０ Alkylsulfonyl, formyl, C １ ~C １０ Alkylcarbonyl, haloC １ ~C １０ Alkylcarbonyl, C １ ~C １０ Alkoxycarbonyl, haloC １ ~C １０ Alkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, HaloC ２ ~C ６ Alkenyl, HaloC ２ ~C ６ Alkynyl, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Alkynyloxy, HaloC ２ ~C ６ Alkenyloxy, HaloC ２ ~C ６ Alkynyloxy, C １ ~C １０ Alkylcarbonyloxy, haloC １ ~C １０ Alkylcarbonyloxy, C １ ~C １０ Cyanoalkyl, C １ ~C １０ Cyanoalkoxy, C １ ~C １０ Alkyl-substituted silyl, substituted or unsubstituted amino, aryl, aryl C １ ~C ６ Alkyl, aryloxy, aryl C １ ~C ６ Alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C １ ~C ６ Alkylsulfonyl, Aryl C １ ~C ６ Alkylsulfinyl, Aryl C １ ~C ６ Alkylthio, heterocyclyl, heterocyclyl C １ ~C ６ Each set of optional substituents is independently selected from alkyl, heterocyclyloxy, halogen, C １ ~C １０ Alkyl, haloC １ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl, haloC ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkoxy, HaloC １ ~C １０ Alkoxy, C ３ ~C １０ Cycloalkoxy, haloC ３ ~C １０ cycloalkoxy; and optionally, Y １ , Y ２ , Y ３ , Y ４ , Y ５ Any two adjacent groups among the above are grouped into a pair, and at least one pair is cyclized with the benzene ring to which it is bonded, with or without at least one heteroatom therebetween, to form at least one 3- to 8-membered ring; Z １ , Z ２ , Z ３ , Z ４ are each independently H, halogen, CN, or NO ２ , C １ ~C １０ Alkyl, haloC １ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl-substituted C １ ~C １０ Alkyl, haloC ３ ~C １０ Cycloalkyl-substituted C １ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl-substituted haloC １ ~C １０ Alkyl, C １ ~C １０ Alkoxy-substituted C １ ~C １０ Alkyl, haloC １ ~C １０ Alkoxy-substituted C １ ~C １０ Alkyl, C １ ~C １０ Alkoxy-substituted haloC １ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl, haloC ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkyl-substituted C ３ ~C １０ Cycloalkyl, haloC １ ~C １０ Alkyl-substituted C ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkyl-substituted haloC ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkoxy, HaloC １ ~C １０ Alkoxy, C １ ~C １０ Alkylthio, HaloC １ ~C １０ Alkylthio, C １ ~C １０ Alkylsulfinyl, HaloC １ ~C １０ Alkylsulfinyl, C １ ~C １０ Alkylsulfonyl, HaloC １ ~C １０ Alkylsulfonyl, formyl, C １ ~C １０ Alkylcarbonyl, haloC １ ~C １０ Alkylcarbonyl, C １ ~C １０ Alkoxycarbonyl, haloC １ ~C １０ Alkoxycarbonyl, arylcarbonyl, aryloxycarbonyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, HaloC ２ ~C ６ Alkenyl, HaloC ２ ~C ６ Alkynyl, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Alkynyloxy, HaloC ２ ~C ６ Alkenyloxy, HaloC ２ ~C ６ Alkynyloxy, C １ ~C １０ Alkylcarbonyloxy, haloC １ ~C １０ Alkylcarbonyloxy, C １ ~C １０ Cyanoalkyl, C １ ~C １０ Cyanoalkoxy, C １ ~C １０ Alkyl-substituted silyl, substituted or unsubstituted amino, aryl, aryl C １ ~C ６ Alkyl, aryloxy, aryl C １ ~C ６ Alkoxy, arylsulfonyl, arylsulfinyl, arylthio, aryl C １ ~C ６ Alkylsulfonyl, Aryl C １ ~C ６ Alkylsulfinyl, Aryl C １ ~C ６ Alkylthio, heterocyclyl, heterocyclyl C １ ~C ６ Each set of optional substituents is independently selected from alkyl, heterocyclyloxy, halogen, C １ ~C １０ Alkyl, haloC １ ~C １０ Alkyl, C ３ ~C １０ Cycloalkyl, haloC ３ ~C １０ Cycloalkyl, C １ ~C １０ Alkoxy, HaloC １ ~C １０ Alkoxy, C ３ ~C １０ Cycloalkoxy, haloC ３ ~C １０ cycloalkoxy; and optionally, Z １ , Z ２ , Z ３ , Z ４ Any two adjacent groups among the above are grouped into a pair, and at least one pair is cyclized with the benzene ring to which it is bonded, with or without at least one heteroatom therebetween, to form at least one 3- to 8-membered ring; And Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ２ , Y ３ , Y ４ are all H and R is ethyl, then Y ５ is not H, fluorine or chlorine, but Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ２ , Y ４ , Y ５ are all H and R is ethyl, then Y ３ is not fluorine or chlorine, Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ３ , Y ５ are all H and R is ethyl, then Y ２ , Y ４ The insecticide and / or acaricide according to claim 1, wherein said compound is not chlorine.

3. In the formula (I), R is C 2 -C 8 alkyl, halo C 2 -C 8 alkyl, C 3 -C 8 cycloalkyl substituted C 2 -C 8 alkyl, halo C 3 -C 8 cycloalkyl substituted C 2 -C 8 alkyl, C 3 -C 8 cycloalkyl substituted halo C 2 -C 8 alkyl, C 1 -C 8 alkoxy substituted C 2 -C 8 alkyl, halo C 1 -C 8 alkoxy substituted C 2 -C 8 alkyl, C 1 -C 8 alkoxy substituted halo C 2 -C 8 alkyl, C 3 -C 8 cycloalkoxy substituted C 2 -C 8 alkyl, halo C 3 -C 8 cycloalkoxy substituted C 2 -C 8 alkyl, C 3 -C 8 cycloalkoxy substituted halo C 2 -C 8 alkyl, C 3 -C 8 cycloalkoxy substituted C 2 -C 8 alkyl, C 3 -C 8 cycloalkoxy substituted halo C 2 -C 8 alkyl, C 3 -C 8 cycloalkyl, halo C 3 -C 8 cycloalkyl, C1-C8 alkyl substituted C3-C8 cycloalkyl, haloC1-C8 alkyl substituted C3-C8 cycloalkyl, C1-C8 alkyl substituted haloC3-C8 cycloalkyl, C1-C8 alkoxy substituted C3-C8 cycloalkyl, haloC1-C8 alkoxy substituted C3-C8 cycloalkyl, C1-C8 alkoxy substituted haloC3-C8 cycloalkyl, C3-C8 cycloalkoxy substituted C3-C8 cycloalkyl, haloC3-C8 cycloalkoxy substituted C3-C8 cycloalkyl, C3-C8 cycloalkoxy substituted haloC3-C8 cycloalkyl, C2-C8 alkenyl, haloC2-C8 alkenyl, C2-C8 alkynyl, haloC 2-C 8 alkynyl; Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are each independently H, halogen, CN, NO 2 , C 1 -C 8 alkyl, haloC 1 -C 8 alkyl, C 3 -C 8 cycloalkyl substituted C 1 -C 8 alkyl, haloC 3 -C 8 cycloalkyl substituted C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl substituted haloC 1 -C 8 alkyl, C 1 -C 8 alkoxy substituted C 1 -C 8 alkyl, haloC 1 -C 8 alkoxy substituted C 1 -C 8 alkyl, C 1 -C 8 alkoxy substituted haloC 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, haloC 3 -C 8 cycloalkyl, C 1 -C 8 alkyl substituted C 3 -C 8 cycloalkyl, haloC 1 1-C8 alkyl substituted C3-C8 cycloalkyl, C1-C8 alkyl substituted haloC3-C8 cycloalkyl, C1-C8 alkoxy, haloC1-C8 alkoxy, C1-C8 alkylthio, haloC1-C8 alkylthio, C1-C8 alkylsulfinyl, haloC1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl, haloC1-C8 alkylsulfonyl; Z 1 , Z 2 , Z 3 and Z 4 are each independently selected from H, halogen, CN, NO 2 , C 1 -C 8 alkyl, haloC 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, haloC 3 -C 8 cycloalkyl, C 1 -C 8 alkoxy, haloC 1 -C 8 alkoxy, C 1 -C 8 alkylthio, haloC 1 -C 8 alkylthio, C 1 -C 8 alkylsulfinyl, haloC 1 -C 8 alkylsulfinyl, C 1 -C 8 alkylsulfonyl and haloC 1 -C 8 alkylsulfonyl; The insecticide / acaricide according to claim 1, wherein when Z1, Z2, Z3, Z4, Y1, Y2, Y3, and Y4 are all H and R is ethyl, Y5 is not H, fluorine, or chlorine; when Z1, Z2, Z3, Z4, Y1, Y2, Y4, and Y5 are all H and R is ethyl, Y3 is not fluorine or chlorine; and when Z1, Z2, Z3, Z4, Y1, Y3, and Y5 are all H and R is ethyl, Y2 and Y4 are not chlorine at the same time.

4. In the formula (I), R is C ２ ~C ８ Alkyl, haloC ２ ~C ８ Alkyl, C ３ ~C ８ Cycloalkyl, haloC ３ ~C ８ Cycloalkyl, C ２ ~C ８ Alkenyl, HaloC ２ ~C ８ Alkenyl, C ２ ~C ８ Alkynyl and haloC ２ ~C ８ alkynyl, Y １ , Y ２ , Y ３ , Y ４ , Y ５ are each independently H, halogen, CN, or NO ２ , C １ ~C ８ Alkyl, haloC １ ~C ８ Alkyl, C ３ ~C ８ Cycloalkyl, haloC ３ ~C ８ Cycloalkyl, C １ ~C ８ Alkoxy, HaloC １ ~C ８ Alkoxy, C １ ~C ８ Alkylthio, HaloC １ ~C ８ Alkylthio, C １ ~C ８ Alkylsulfinyl, HaloC １ ~C ８ Alkylsulfinyl, C １ ~C ８ Alkylsulfonyl, HaloC １ ~C ８ alkylsulfonyl; Z １ , Z ２ , Z ３ , Z ４ are each independently H, halogen, CN, or NO ２ , C １ ~C ８ Alkyl, haloC １ ~C ８ Alkyl, C １ ~C ８ Alkoxy, HaloC １ ~C ８ Alkoxy, C １ ~C ８ Alkylthio, haloC １ ~C ８ Alkylthio, C １ ~C ８ Alkylsulfinyl, HaloC １ ~C ８ Alkylsulfinyl, C １ ~C ８ Alkylsulfonyl, HaloC １ ~C ８ alkylsulfonyl; And Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ２ , Y ３ , Y ４ are all H and R is ethyl, then Y ５ is not H, fluorine or chlorine, but Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ２ , Y ４ , Y ５ are all H and R is ethyl, then Y ３ is not fluorine or chlorine, Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ３ , Y ５ are all H and R is ethyl, then Y ２ , Y ４ The insecticide and / or acaricide according to any one of claims 1 to 3, wherein said compound is not chlorine.

5. In the formula (I), R is C ２ ~C ８ Alkyl, haloC ２ ~C ８ Alkyl, C ３ ~C ８ Cycloalkyl, haloC ３ ~C ８ Cycloalkyl, C ２ ~C ５ Alkenyl, C ２ ~C ５ alkynyl, Y １ , Y ２ , Y ３ , Y ４ , Y ５ are each independently H, halogen, CN, or NO ２ , C １ ~C ８ Alkyl, haloC １ ~C ８ Alkyl, C １ ~C ８ Alkoxy, HaloC １ ~C ８ alkoxy; Z １ , Z ２ , Z ３ , Z ４ are each independently H, halogen, CN, or NO ２ , C １ ~C ８ Alkyl, haloC １ ~C ８ Alkyl, C １ ~C ８ Alkoxy, HaloC １ ~C ８ alkoxy; And Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ２ , Y ３ , Y ４ are all H and R is ethyl, then Y ５ is not H, fluorine or chlorine, but Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ２ , Y ４ , Y ５ are all H and R is ethyl, then Y ３ is not fluorine or chlorine, Z １ , Z ２ , Z ３ , Z ４ , Y １ , Y ３ , Y ５ are all H and R is ethyl, then Y ２ , Y ４ The insecticide and / or acaricide according to any one of claims 1 to 4, wherein said compound is not chlorine.

6. In the formula (I), R is selected from ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, s-butyl, isobutyl, t-butyl, allyl, propargyl, CF 3 ; Y1, Y2, Y3, Y4, and Y5 are each independently selected from H, F, Cl, Br, I, CN, NO2, CH3, CF3, OCH3, OCF3, OCH2CF3, OCH2CF2CF3, CF2Cl, CFCl2, and CCl3; Z 1 , Z 2 , Z 3 , and Z 4 are each independently selected from H, F, Cl, Br, I, CN, NO 2 , CH 3 , CF 3 , OCF 3 , ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl, and t-butyl; The insecticide / acaricide according to any one of claims 1 to 4, wherein when Z1, Z2, Z3, Z4, Y1, Y2, Y3, and Y4 are all H and R is ethyl, Y5 is not H, fluorine, or chlorine; when Z1, Z2, Z3, Z4, Y1, Y2, Y4, and Y5 are all H and R is ethyl, Y3 is not fluorine or chlorine; and when Z1, Z2, Z3, Z4, Y1, Y3, and Y5 are all H and R is ethyl, Y2 and Y4 are not chlorine at the same time.

7. In the formula (I), R is selected from ethyl, n-propyl, isopropyl, n-butyl, s-butyl, isobutyl; Y1, Y2, Y3, Y4, and Y5 are each independently selected from H, F, Cl, Br, CN, NO2, OCF3, CH3, CF3, OCH3, OCH2CF3, and OCH2CF2CF3; Z 1 , Z 2 , Z 3 , and Z 4 are each independently selected from H, F, Cl, Br, and CH 3 ; The insecticide / acaricide according to any one of claims 1 to 4, wherein when Z1, Z2, Z3, Z4, Y1, Y2, Y3, and Y4 are all H and R is ethyl, Y5 is not H, fluorine, or chlorine; when Z1, Z2, Z3, Z4, Y1, Y2, Y4, and Y5 are all H and R is ethyl, Y3 is not fluorine or chlorine; and when Z1, Z2, Z3, Z4, Y1, Y3, and Y5 are all H and R is ethyl, Y2 and Y4 are not chlorine at the same time.

8. An insecticide / acaricide according to any one of claims 1 to 7, wherein the content of the active ingredient is 1 to 99 weight % relative to the total weight of the insecticide / acaricide.

9. An insecticide / acaricide according to any one of claims 1 to 7, wherein the content of the active ingredient is 5 to 60% by weight based on the total weight of the insecticide / acaricide.

10. Use of the insecticide and / or acaricide according to any one of claims 1 to 9 in agricultural, forestry and horticultural insecticide and / or acaricide.

Images