A compound containing a benzimidazolone structure, application thereof and a herbicide

Abstract

This invention relates to the field of pesticides and herbicides, and discloses a compound containing a benzimidazole structure, its application, and a herbicide. The compound has the structure shown in formula (I). The aforementioned compound containing a benzimidazole structure provided by this invention exhibits high herbicidal activity against broadleaf weeds, grass weeds, and sedge weeds.

Description

Technical Field

[0001] This invention relates to the field of pesticides and herbicides, specifically to a compound containing a benzimidazole ketone structure, its application, and a herbicide. Background Technology

[0002] Herbicides, as an important agricultural input, play an indispensable role in ensuring food security. However, due to the long-term irrational and unscientific use of herbicides, the problem of weed resistance has become increasingly prominent, urgently requiring the development of ultra-efficient herbicides with novel mechanisms of action and low risk of resistance.

[0003] p-Hydroxyphenylpyruvate dioxidase (HPPD) is one of the most important herbicide targets, widely present in various aerobic organisms. It catalyzes the conversion of p-hydroxyphenylpyruvate (HPPA) into homogentisic acid (HGA). In plants, HGA is further converted into plastoquinone and tocopherol. Plastoquinone is a carrier in the photosynthetic electron transport chain, and tocopherol is an important antioxidant that protects cells from singlet oxygen damage. If HPPD is inhibited in plants, the synthesis of plastoquinone and tocopherol will be hindered, thereby affecting the biosynthesis of carotenoids, which in turn affects photosynthesis, ultimately leading to bleaching and death of weeds.

[0004] Inhibitors targeting HPPD are characterized by high efficiency, broad spectrum, low toxicity, environmental friendliness, and slow resistance development. Furthermore, these inhibitors do not exhibit cross-resistance with other types of herbicides.

[0005] Therefore, HPPD-inhibiting herbicides have significant research value and development prospects. Summary of the Invention

[0006] The purpose of this invention is to provide a class of compounds containing a benzimidazole ketone structure so that such compounds can be used as pesticide herbicides to control agricultural weeds.

[0007] To achieve the above objectives, a first aspect of the present invention provides a compound containing a benzimidazolone structure, the compound having the structure shown in formula (I). , , In equation (I), R 1 C1-C is H, unsubstituted, or substituted by at least one group in combination A. 12 Alkyl, unsubstituted or substituted by at least one group in combination A, C2-C 12 The alkenyl, unsubstituted or substituted C2-C group of combination A 12The alkynyl group, unsubstituted or substituted with at least one group from combination A, is a six-membered unsaturated aromatic heterocyclic alkyl group containing 1-3 N atoms as cyclic atoms, or -(CH2). m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 For C1-C 12 Alkyl group; m is an integer from 0 to 6; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a cyano group, or a C1-C1 group. 12 alkoxy groups, -SO2-R 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C6 alkyl groups; R 10 For C1-C 12 Any one of the alkyl groups; the combination B contains C1-C 12 Alkyl, C1-C 12 Alkyl, halogen, nitro, cyano, and C1-C6 alkyl groups substituted with at least one halogen; R 2 For C1-C 12 Any one of alkyl, C3-C6 cycloalkyl, and phenyl groups; X is a halogen, -S(O) n -R x Nitro, cyano, -C(O) n -R x C1-C substituted by at least one halogen 12 Any one of the alkyl groups; n is 0, 1, or 2; R x C1-C that is unsubstituted or substituted by at least one halogen 12 Any one of the alkyl groups; Q is any one of the groups in formula (Q1), formula (Q2), formula (Q3), and formula (Q4); In equation (Q1), R 3 R 4 R 5 R 6 Each is independently selected from H and C1-C6 alkyl groups; In equation (Q2), R 7 Selected from H, C2-C 12 alkynyl group, C2-C 12 alkenyl, -S(O) n -R y -C(O)n -R y ;R y C1-C that is unsubstituted or substituted by at least one halogen 12 Alkyl groups, five- or six-membered unsaturated aromatic heterocyclic alkyl groups containing 0-3 nitrogen atoms as cyclic atoms, or phenyl groups; R 8 Selected from C1-C 12 Alkyl group; R 9 Selected from H, C1-C 12 Alkyl groups, C3-C6 cycloalkyl groups; In equation (Q3), R 10 Selected from C1-C 12 Alkyl groups; In equation (Q4), R 11 Selected from C1-C 12 Alkyl groups.

[0008] A second aspect of the present invention provides the use of the compounds containing the benzimidazole structure described in the first aspect in the control of weeds.

[0009] A third aspect of the present invention provides a herbicide containing an effective amount of the compound with the benzimidazole structure described in the first aspect for controlling weeds.

[0010] The compounds containing benzimidazole ketone structures provided by this invention have high herbicidal activity against broadleaf weeds, grass weeds, and sedge weeds. Detailed Implementation

[0011] The endpoints and any values ​​of the ranges 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 endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0012] The compounds of this invention can exist in pure form or as mixtures of different possible isomers (e.g., stereoisomers or structural isomers). Various stereoisomers include enantiomers, diastereomers, chiral isomers, rotation-resistant isomers, conformational isomers, rotational isomers, tautomers, optical isomers, polymorphs, and geometric isomers. Any possible mixture of these isomers falls within the scope of the claims of this disclosure. Those skilled in the art will understand that a stereoisomer may be more active and / or may exhibit beneficial effects when enriched or separated from other isomers. Furthermore, processes or methods for separating, enriching, and / or selectively preparing said isomers are known to those skilled in the art.

[0013] Used alone or in compound words (e.g., "alkoxy" or "halogen-substituted C") 1-12 The term "alkyl" as used in the context of "alkyl group" includes straight-chain or branched alkyl groups. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- Dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl, or different isomers. If the alkyl group is at the end of the complex substituent, for example in an alkylcycloalkyl group, the starting portion of the complex substituent, such as a cycloalkyl group, may be mono- or poly-substituted by the alkyl group, either identically or differently, and independently. This also applies to complex substituents in which other groups (e.g., alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy, etc.) are at the end. Unsubstituted or substituted C1-C groups from combination A. 12 Alkyl groups, indicating that when C1-C 12 When the alkyl group is substituted, it can be at C1-C 12 Substitution occurs at any position on the alkyl group that can be substituted, and the substituent is selected from at least one of combination A, wherein the number of carbon atoms present in the substituent is not counted in the "C1-C" group. 12 In the alkyl group of 1-12.

[0014] The term "alkenyl" used alone or in compound words includes straight-chain or branched alkenes. Non-limiting examples of alkenes include vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, and 3-methyl-2-butenyl. 1-Methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2- Pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, l,3-dimethyl-2-butenyl, l,3-dimethyl-3-butenyl, 2,2-dimethyl-3 -Butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl, as well as various isomers. "Alkenyl" also includes polyenes, such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl groups that are part of a complex substituent, such as haloalkenyl groups, unless otherwise specifically defined. C2-C unsubstituted or substituted by at least one group in combination A 12 The alkenyl group indicates that when C2-C 12 When the alkenyl group is substituted, it can be at C2-C12 Substitution occurs at any position on the alkenyl group that can be substituted, and the substituent is selected from at least one of combination A. The number of carbon atoms present in the substituent is not counted in the "C2-C" group. 12 In the 2-12 of the "alkenyl".

[0015] Non-limiting examples of the term "alkynyl" used alone or in compound words include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl- 3-Pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2-propynyl, as well as various isomers. This definition also applies to alkynyl groups that are part of a complex substituent, such as halogenated alkynyl groups, unless otherwise specifically defined. The term "alkynyl" may also include a portion consisting of multiple triple bonds, such as 2,5-hexamethylenediynyl. C2-C unsubstituted or substituted by at least one group in combination A 12 The alkynyl group indicates that when C2-C 12 When the alkynyl group is substituted, it can be at C2-C 12 Substitution occurs at any position on the alkynyl group that is capable of substitution, and the substituent is selected from at least one of combination A. The number of carbon atoms present in the substituent is not counted in the "C2-C" group. 12 In the 2-12 of the "alkynyl group".

[0016] The term "halogen," whether used alone or in compound words (such as "halogen-substituted C"), 1-12 Alkyl groups, including fluorine, chlorine, bromine, or iodine. Furthermore, when used in compound terms, the hydrogen atoms on the group may be partially or completely replaced by halogen atoms, which may be the same or different. (The last part, "halogen-substituted C," appears to be a separate, unrelated sentence.) 1-12Taking "alkyl" as an example, non-limiting examples include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, and 1,1,1-trifluoropropyl-2-yl. This definition also applies to haloalkyl groups that are part of a complex substituent, such as haloalkylaminoalkyl groups, unless otherwise specifically defined.

[0017] Examples of the term "alkoxy" used alone or in compound words include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentooxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy The substituents include alkyl, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy, as well as their various isomers. This definition also applies to alkoxy groups that are part of a complex substituent, such as haloalkoxy, alkynylalkoxy, etc., unless otherwise specifically defined.

[0018] In this invention, when a group contains a substituent that can be hydrogen, the group is considered unsubstituted when the substituent is considered to be hydrogen.

[0019] If appropriate, the compounds of the present invention may exist in mixtures of different possible isomers, especially stereoisomers such as E and Z, threotypes and erythrotypes, and optical isomers, but also tautomers if appropriate. Any desired mixtures of these isomers and possible tautomers, including E and Z isomers, threotypes and erythrotypes, and optical isomers, are disclosed and claimed.

[0020] The definition of "aromatic" in the group described in this invention is adopted in a broad sense within the field of organic chemistry.

[0021] In the structural formula of this invention, the wavy lines all represent connection points.

[0022] As previously described, a first aspect of the present invention provides a compound containing a benzimidazolone structure having the structure shown in formula (I). , , In equation (I), R 1 C1-C is H, unsubstituted, or substituted by at least one group in combination A. 12 Alkyl, unsubstituted or substituted by at least one group in combination A, C2-C 12 The alkenyl, unsubstituted or substituted C2-C group of combination A 12 The alkynyl group, unsubstituted or substituted with at least one group from combination A, is a six-membered unsaturated aromatic heterocyclic alkyl group containing 1-3 N atoms as cyclic atoms, or -(CH2). m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 For C1-C 12 Alkyl group; m is an integer from 0 to 6; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a cyano group, or a C1-C1 group. 12 alkoxy groups, -SO2-R 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C6 alkyl groups; R 10 For C1-C 12 Any one of the alkyl groups; the combination B contains C1-C 12 Alkyl, C1-C 12 Alkyl, halogen and nitro, cyano, C1-C6 alkyl groups substituted with at least one halogen; R 2 For C1-C 12 Any one of alkyl, C3-C6 cycloalkyl, and phenyl groups; X is a halogen, -S(O) n -R x Nitro, cyano, -C(O) n -R x C1-C substituted by at least one halogen 12 Any one of the alkyl groups; n is 0, 1, or 2; R x C1-C that is unsubstituted or substituted by at least one halogen 12 Any one of the alkyl groups; Q is any one of the groups in formula (Q1), formula (Q2), formula (Q3), and formula (Q4); In equation (Q1), R 3 R 4 R 5 R 6 Each is independently selected from H and C1-C6 alkyl groups; In equation (Q2), R 7 Selected from H, C2-C 12 alkynyl group, C2-C 12 alkenyl, -S(O) n -R y -C(O) n -R y ;R y C1-C that is unsubstituted or substituted by at least one halogen 12 Alkyl groups, five- or six-membered unsaturated aromatic heterocyclic alkyl groups containing 0-3 nitrogen atoms as cyclic atoms, or phenyl groups; R 8 Selected from C1-C 12 Alkyl group; R 9 Selected from H, C1-C 12 Alkyl groups, C3-C6 cycloalkyl groups; In equation (Q3), R 10 Selected from C1-C 12 Alkyl groups; In equation (Q4), R 11 Selected from C1-C 12 Alkyl groups.

[0023] Preferably, in formula (I), R 1 C1-C is H, unsubstituted, or substituted by at least one group in combination A. 10 Alkyl, unsubstituted or substituted by at least one group in combination A, C2-C 10 The alkenyl, unsubstituted or substituted C2-C group of combination A 10 The alkynyl group, unsubstituted or substituted with at least one group from combination A, is a six-membered unsaturated aromatic heterocyclic alkyl group containing 1-3 N atoms as cyclic atoms, or -(CH2). m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 For C1-C 10Alkyl group; m is an integer from 0 to 4; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, C1-C 10 alkoxy groups, -SO2-R 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 For C1-C 10 Any one of the alkyl groups; the combination B contains C1-C 10 Alkyl, C1-C 10 alkoxy, halogen, and nitro groups; R 2 For C1-C 10 Any one of the alkyl groups; X is a halogen, -S(O) n -R x Nitro, cyano, C1-C substituted with at least one halogen 10 Any one of the alkyl groups; n is 0, 1, or 2; R x C1-C that is unsubstituted or substituted by at least one halogen 10 Any one of the alkyl groups; Q is any one of the groups in formula (Q1), formula (Q2), formula (Q3), and formula (Q4); In equation (Q1), R 3 R 4 R 5 R 6 Each is independently selected from H and C1-C4 alkyl groups; In equation (Q2), R 7 Selected from H, C2-C 10 alkynyl group; R 8 and R 9 Each is independently selected from C1-C 10 Alkyl groups; In equation (Q3), R 10 Selected from C1-C 10 Alkyl groups; In equation (Q4), R 11 Selected from C1-C 12 Alkyl groups.

[0024] More preferably, in equation (I), R 1The following are unsubstituted C1-C6 alkyl groups, unsubstituted C2-C6 alkenyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted six-membered unsaturated aromatic heterocyclic alkyl groups containing 1-2 N atoms as cyclizing atoms, or -(CH2) substituted by H, unsubstituted or substituted by at least one group in combination A. m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 It is a C1-C6 alkyl group; m is an integer from 0 to 3; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a C1-C6 alkoxy group, or -SO2-R. 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 It is any one of C1-C6 alkyl groups; the combination B contains C1-C6 alkyl groups, C1-C6 alkoxy groups, halogens and nitro groups; R 2 It is any one of the alkyl groups from C1 to C6; X is a halogen, -S(O) n -R x Any one of C1-C6 alkyl groups substituted with at least one halogen; n is 0, 1, or 2; R x It is any one of the alkyl groups from C1 to C6; Q is any one of the groups in formula (Q1), formula (Q2), formula (Q3), and formula (Q4); In equation (Q1), R 3 R 4 R 5 R 6 Each is independently selected from H, C1-C3 alkyl groups; In equation (Q2), R 7 Selected from H, C2-C6 alkynyl groups; R 8 and R 9 Each alkyl group is independently selected from C1-C6; In equation (Q3), R 10 Alkyl groups selected from C1-C6; In equation (Q4), R 11 Alkyl groups selected from C1-C6.

[0025] According to the preferred embodiment 1, in formula (I), R 1 The following are unsubstituted C1-C6 alkyl groups, unsubstituted C2-C6 alkenyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted six-membered unsaturated aromatic heterocyclic alkyl groups containing 1-2 N atoms as cyclizing atoms, or -(CH2) substituted by H, unsubstituted or substituted by at least one group in combination A. m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 It is a C1-C6 alkyl group; m is an integer from 0 to 3; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a C1-C6 alkoxy group, or -SO2-R. 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 It is any one of C1-C6 alkyl groups; the combination B contains C1-C6 alkyl groups, C1-C6 alkoxy groups, halogens and nitro groups; R 2 It is any one of the alkyl groups from C1 to C6; X can be F, Cl, Br, or -S(O). n -R x Any one of C1-C6 alkyl groups substituted with at least one halogen; n is 0, 1, or 2; R x It is any one of C1-C4 alkyl groups; Q is the group represented by formula (Q1); in formula (Q1), R 3 R 4 R 5 R 6 Each is independently selected from H, methyl, ethyl, n-propyl, and isopropyl.

[0026] In the preferred embodiment 1, more preferably, the compound represented by formula (I) has the structure represented by formula (I-Q1). Formula (I-Q1), In equation (I-Q1), R 3 R 4 R 5 R 6 Both are H; R 1 R2 The definitions of X are shown in Table 1 for compounds 1 to 371.

[0027] According to the preferred embodiment 2, in formula (I), R 1 The following are unsubstituted C1-C6 alkyl groups, unsubstituted C2-C6 alkenyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted six-membered unsaturated aromatic heterocyclic alkyl groups containing 1-2 N atoms as cyclizing atoms, or -(CH2) substituted by H, unsubstituted or substituted by at least one group in combination A. m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 It is a C1-C6 alkyl group; m is an integer from 0 to 3; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a C1-C6 alkoxy group, or -SO2-R. 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 It is any one of C1-C6 alkyl groups; the combination B contains C1-C6 alkyl groups, C1-C6 alkoxy groups, halogens and nitro groups; R 2 It is any one of the alkyl groups from C1 to C6; X can be F, Cl, Br, or -S(O). n -R x Any one of C1-C6 alkyl groups substituted with at least one halogen; n is 0, 1, or 2; R x It is any one of C1-C4 alkyl groups; Q is the group represented by formula (Q2); in formula (Q2), R 7 Selected from H, C2-C4 alkynyl groups; R 8 and R 9 Each is independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl.

[0028] In a preferred embodiment 2, more preferably, the compound represented by formula (I) has the structure represented by formula (I-Q2). Formula (I-Q2) In equation (I-Q2), R 8 and R9 All are methyl; R 1 R 2 R 7 The definitions of X are shown in compounds 372 to 744 in Table 2.

[0029] According to the preferred embodiment 3, in formula (I), R 1 The following are unsubstituted C1-C6 alkyl groups, unsubstituted C2-C6 alkenyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted six-membered unsaturated aromatic heterocyclic alkyl groups containing 1-2 N atoms as cyclizing atoms, or -(CH2) substituted by H, unsubstituted or substituted by at least one group in combination A. m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 It is a C1-C6 alkyl group; m is an integer from 0 to 3; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a C1-C6 alkoxy group, or -SO2-R. 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 It is any one of C1-C6 alkyl groups; the combination B contains C1-C6 alkyl groups, C1-C6 alkoxy groups, halogens and nitro groups; R 2 It is any one of the alkyl groups from C1 to C6; X can be F, Cl, Br, or -S(O). n -R x Any one of C1-C6 alkyl groups substituted with at least one halogen; n is 0, 1, or 2; R x It is any one of C1-C4 alkyl groups; Q is the group represented by formula (Q3); in formula (Q3), R 10 Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl.

[0030] In a preferred embodiment 3, more preferably, the compound represented by formula (I) has the structure represented by formula (I-Q3). Formula (I-Q3) In equation (I-Q3), R10 Methyl; R 1 R 2 The definitions of X are shown in Table 3 for compounds 745 to 1116.

[0031] According to the preferred embodiment 4, in formula (I), R 1 The following are unsubstituted C1-C6 alkyl groups, unsubstituted C2-C6 alkenyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted six-membered unsaturated aromatic heterocyclic alkyl groups containing 1-2 N atoms as cyclizing atoms, or -(CH2) substituted by H, unsubstituted or substituted by at least one group in combination A. m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 It is a C1-C6 alkyl group; m is an integer from 0 to 3; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a C1-C6 alkoxy group, or -SO2-R. 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 It is any one of C1-C6 alkyl groups; the combination B contains C1-C6 alkyl groups, C1-C6 alkoxy groups, halogens and nitro groups; R 2 It is any one of the alkyl groups from C1 to C6; X can be F, Cl, Br, or -S(O). n -R x Any one of C1-C6 alkyl groups substituted with at least one halogen; n is 0, 1, or 2; R x It is any one of C1-C4 alkyl groups; Q is the group represented by formula (Q4); in formula (Q4), R 11 Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl.

[0032] In a preferred embodiment 4, more preferably, the compound represented by formula (I) has the structure represented by formula (I-Q4). Formula (I-Q4) In equation (I-Q4), R 11 Methyl; R1 R 2 The definitions of X are shown in compounds 1117 to 1487 in Table 4.

[0033] According to the preferred embodiment 5, the compound shown in formula (I) is selected from any one of compound 1 to compound 1487.

[0034] This invention does not impose any particular limitations on the specific methods for preparing the aforementioned compounds containing benzimidazolone structures. Those skilled in the art can obtain the aforementioned compounds of this invention by combining the specific structural formulas provided by this invention with known knowledge in the field of organic synthesis. Furthermore, the following description of this invention exemplifies the preparation methods of some compounds. Those skilled in the art can also obtain the specific preparation methods of all other compounds by substituting the types of raw materials according to the preparation methods of the compounds described later in this invention. This invention will not elaborate on the preparation methods of all compounds, and this should not be construed as a limitation of the invention.

[0035] As previously stated, a second aspect of the present invention provides the use of compounds containing the benzimidazole structure described in the first aspect in weed control.

[0036] Preferably, the weeds include broadleaf weeds, grass weeds, and sedge weeds.

[0037] Preferably, the broadleaf weeds are selected from at least one of the following: shepherd's purse, lambsquarters, velvetleaf, cleavers, speedwell, chickweed, amaranth, black nightshade, lantern grass, purslane, amaranth retroflexus, and carp intestines.

[0038] Preferably, the grassy weeds are selected from at least one of the following: barnyard grass, goosegrass, golden foxtail grass, foxtail grass, crabgrass, wild oat, Japanese wild oat, jointed barnyard grass, wild oat, wild oat, barnyard grass, and double-spike barnyard grass.

[0039] Preferably, the sedge is selected from at least one of Cyperus rotundus and Cyperus divaricata.

[0040] As previously described, a third aspect of the present invention provides a herbicide containing an effective amount of the compound with the benzimidazole structure described in the first aspect (as an active ingredient).

[0041] Preferably, the herbicide also contains pesticide formulation excipients.

[0042] Preferably, the pesticide formulation excipients are selected from at least one of solvents, emulsifiers, dispersants, wetting agents, stabilizers, thickeners, antifreeze agents, preservatives, fillers, colorants, and defoamers.

[0043] The solvent is used to dissolve or dilute the active ingredient of the pesticide, and common solvents include water, alcohols (such as ethanol and isopropanol), ketones (such as acetone), and aromatic hydrocarbons (such as toluene and xylene). The emulsifier helps the active ingredient of the pesticide to disperse evenly in water, forming a stable emulsion; commonly used are nonionic surfactants (such as alkylphenol polyoxyethylene ethers) and anionic surfactants (such as sodium dodecylbenzene sulfonate). The dispersant prevents solid particles from agglomerating and ensures uniform suspension; commonly used are lignin sulfonates and naphthalene sulfonates. The wetting agent reduces the surface tension of the liquid, enhancing the adhesion and penetration of the pesticide solution onto the plant surface; commonly used are alkyl sulfates and alkylbenzene sulfonates. The stabilizer prevents the pesticide from decomposing during storage or use; commonly used are antioxidants (such as BHT and BHA) and ultraviolet absorbers (such as benzotriazoles). The thickener adjusts the viscosity of the formulation and improves flowability; commonly used are xanthan gum and carboxymethyl cellulose. The antifreeze prevents the liquid pesticide from freezing at low temperatures; commonly used are ethylene glycol and propylene glycol. The preservatives prevent microbial contamination and extend shelf life; commonly used preservatives include sodium benzoate and potassium sorbate. The fillers are used in solid pesticide formulations to increase volume or adjust flowability; commonly used fillers include talc, kaolin, and diatomaceous earth. The colorants are used to identify pesticide types or improve visibility; commonly used colorants include dyes or pigments. The defoamers prevent or eliminate foaming during formulation production and use; commonly used defoamers are silicone-based.

[0044] Preferably, the formulation of the herbicide is selected from at least one of wettable powder (WP), water-dispersible granules (WG), emulsifiable concentrate (EC), suspension concentrate (SC), aqueous solution (AS), granules (GR), soluble powder (SP), microcapsule suspension (CS), oil suspension (OD), emulsion (EW), effervescent tablets (ET), and fumigant (FG).

[0045] Furthermore, the present invention does not particularly limit the specific types of excipients, such as inert carriers or any other basic components, such as surfactants, additives, solid diluents and liquid diluents.

[0046] For example, suitable excipients can be solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, auxiliaries, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, viscous agents and adhesives.

[0047] For example, suitable solvents and liquid carriers for excipients are water and organic solvents, such as medium to high boiling point mineral oil fractions, such as kerosene and diesel; oils of vegetable or animal origin; aliphatic, cyclic, and aromatic hydrocarbons, such as toluene, paraffin, tetrahydronaphthalene, and alkylated naphthalene; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, and cyclohexanol; diols; DMSO; ketones, such as cyclohexanone; esters, such as lactates, carbonates, fatty acid esters, and γ-butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone and fatty acid dimethylamide; and mixtures thereof. Suitable solid carriers or fillers are mineral soils, such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, and magnesium oxide; polysaccharides, such as cellulose and starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and urea; and plant-derived products, such as cereal flour, bark flour, wood flour, and nut shell flour, as well as mixtures thereof.

[0048] Suitable surfactants for use as excipients in this invention are surfactant compounds, such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. These surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or auxiliaries.

[0049] Suitable anionic surfactants used as excipients in this invention are alkali metal, alkaline earth metal, or ammonium salts of sulfonic acids, sulfuric acids, phosphoric acids, and carboxylic acids, as well as mixtures thereof. Examples of sulfonates are alkyl aryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalene and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamides. Examples of sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, or sulfates of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0050] Suitable nonionic surfactants used as excipients in this invention are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl surfactants, polymeric surfactants, and mixtures thereof.

[0051] Examples of N-substituted fatty acid amides used as excipients in this invention are fatty acid glucosamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerides, or monoglycerides. Examples of glycosyl surfactants are sorbitol, ethoxylated sorbitol, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[0052] Suitable cationic surfactants used as excipients in this invention are quaternary surfactants, such as quaternary ammonium compounds having one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers containing blocks of polyethylene oxide and polypropylene oxide, or ABC type block polymers containing alkanols, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers.

[0053] Suitable adjuvants for this invention are compounds that possess negligible pesticide activity or even no pesticide activity themselves, but improve the biological properties of the compound against the target analyte. Examples include surfactants, mineral or vegetable oils, and other adjuvants.

[0054] Suitable thickeners for use as excipients in this invention are polysaccharides (e.g., xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0055] Suitable bactericides used as excipients in this invention are bromonitrile glycol and isothiazolinone derivatives such as alkylisothiazolinone and benzisothiazolinone.

[0056] Suitable antifreeze agents used as excipients in this invention are ethylene glycol, propylene glycol, urea, and glycerin.

[0057] Suitable defoamers used as excipients in this invention are polysiloxanes, long-chain alcohols, and fatty acid salts.

[0058] Suitable colorants (e.g., red, blue, or green) used as excipients in this invention are low-water-soluble pigments and water-soluble dyes. Examples include inorganic colorants (e.g., iron oxide, titanium oxide, ferric hexacyanate ferrite) and organic colorants (e.g., alizarin colorants, azo colorants, and phthalocyanine colorants).

[0059] Suitable thickeners or adhesives used as excipients in this invention are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biowax or synthetic wax, and cellulose ether.

[0060] Preferably, the active ingredient in the herbicide is present in an amount of 0.1-99.99 wt%, for example, it can be 0.5 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, 75 wt%, 80 wt%, 85 wt%, 90 wt%, 91 wt%, 92 wt%, 93 wt%, 94 wt%, 95 wt%, 96 wt%, 97 wt%, 98 wt%, or 99 wt%.

[0061] The compounds containing benzimidazole one structures provided by this invention have excellent crop safety.

[0062] The crops described in this invention can be plants that can be obtained through conventional breeding and optimization methods or through biotechnology and genetic engineering methods or a combination of these methods, including transgenic plants and plant cultivars protected and unprotected by plant breeders.

[0063] Examples of crops described in this invention include, but are not limited to, agricultural crops such as wheat, rye, barley, triticale, oats, or rice; sugar beets, such as sugar beets or fodder beets; fruits and fruit trees, such as pome, stone fruit, or soft fruit, such as apple, pear, plum, peach, almond, cherry, strawberry, raspberry, blackberry, or gooseberry; legumes, such as lentils, peas, alfalfa, or soybeans; oilseed plants, such as rape, mustard, olive, sunflower, coconut, cocoa bean, castor oil plants, oil palm, peanut, or soybeans; cucurbitaceous plants, such as squash, cucumber, or melons; fiber plants, such as cotton, flax, hemp, or jute; citrus fruits and citrus trees, such as oranges, lemons, grapefruits, or mandarins; any horticultural plants and vegetables, such as spinach, lettuce, etc. Lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits, or red peppers; Lauraceae plants, such as avocados, cinnamon, or camphor; Cucurbitaceae; oil plants; energy and raw material plants, such as cereals, corn, soybeans, other legumes, rapeseed, sugarcane, or oil palm; tobacco; nuts; coffee; tea; cocoa; bananas; peppers; grapevines (table grapes and grape juice vines); hops; turf; stevia (also known as sweet stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broadleaf trees, or evergreens, such as conifers; and plant propagation materials, such as seeds, and crop materials of these plants.

[0064] Preferably, the crops described in this invention include, but are not limited to, cereal crops, corn, rice, soybeans and other legumes, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oil-producing plants, tobacco, coffee, tea, cocoa, sugar beets, sugarcane, cotton, potatoes, tomatoes, onions, peppers and vegetables, ornamental plants, any flowering plants and other plants for human and animal use.

[0065] The crop described in this invention includes all parts and organs of the crop, including but not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots (including taproot, lateral roots, root hairs, root tips, and root cap), rhizomes, slips, shoots, fruits, fruiting bodies, bark, stem, buds, axillary buds, meristems, nodes, and internodes.

[0066] Based on the compounds described in this invention, it may also be mixed with other insecticidal active substances such as insecticides, acaricides, herbicides and fungicides, or with safeners, fertilizers and / or plant growth regulators. The mixing method may be pre-mixed or bottled.

[0067] In compound formulations or tank-mixed formulations, suitable active substances that can be mixed with the active substances of the present invention are known substances in the cited literature (e.g., *World Encyclopedia of New Pesticide Varieties*, China Agricultural Science and Technology Press, 2010.9). For example, the following herbicidal active substances can be mixed with the compounds of the present invention: metolachlor, propargite, quinalazine, pyraclostrobin, flusulfuron-methyl, heptamethrin, chlorpyrifos, acetamiprid, pendimethalin, benzylsulfuron-methyl, diquat chloride, clodinafop-methyl, atrazine, chlorsulfuron-methyl, metsulfuron-methyl, benzylsulfuron-methyl, thiamethoxam, pyrazuron-methyl, and formamide. Pyrimethanil, methyl pyrimethanil, nicosulfuron, amphetamine, acyl pyrimethanil, cypromethanil, sulfadiazine, pyrimisulfuron, fluazinam, trifluralin, flusulfanilamide, quizalofop-P-ethyl, ethoxysulfuron, glufosinate, bensulfuron, chlorfluazuron, ethyl ester, methyl methoxysulfuron, trifluralin, fluorinated oxysulfuron, propyzoxystrobin, bensulfuron-methyl, fluazinam, 2,4-D butyl ester, 2,4-D sodium chloride, 2 4-D isooctyl ester, quizalofop-P-ethyl, quizalofop-P-ethyl, quizalofop-P-ethyl, quizalofop-P-ethyl, cyhalofop-butyl, oxazolidinyl, clodinafop-propargyl, glyphosate, glufosinate, imazaloxic acid, imazaloxic acid, imazaloxic acid, methoxymethylene, dichloropyridine, ammoniapyridine, benzoxazine, ethazine, diflubenzuron, penoxsulam, sulfadiazine, chlorpyrifos, cyclopyrazosulfuron, pyrimethanil, pyrimethanil, pyrimethanil, dicyclopyrazosulfuron, nitrate Sulfamethrin, sulfadiazine, cyclosulfadiazine, furazolidone, flupyrazole, cyclopyrazole, cyclopyrazole, cyclopyrazole, cyclopyrazole, cyclopyrazole, cyclopyrazole, cyclopyrazole, cyclopyrazole, cyclopyrazole, cyclopyrazole, cyclopyrazole, cyclopyrazole, cyclopyrazole, dichloropropene, dichloropropene, fluchloropyridine ester, chlorofluoropyridine ester, indolepyridine ester, flupyrazole, flusulfanilamide, trifluralin, flupropyrazol, flupyrimisulfuron, flupyrimisulfuron, pyrimisulfuron, cyclopyrazole, cyclopyrazole, etc.

[0068] When used, commercially available formulations are diluted in a common manner if necessary, such as with water for wettable powders, concentrated emulsions, suspensions, and granules suspended in water. Powders, granules for soil application, or solutions for broadcasting and spraying generally do not require further dilution with an inert substance before use. The required amount of the compound of the invention used varies with external conditions, such as temperature, humidity, and the nature of the herbicide used. It can vary considerably, for example, from 0.001 to 1.0 kg ai / ha, or more active ingredient, but is preferably from 0.005 to 500 g ai / ha, particularly from 0.005 to 250 g ai / ha.

[0069] The compounds or agents described in this invention can be applied to the environment including soil, plants or plant parts, and to equipment or tools used before, during or after sowing / planting plants or plant parts.

[0070] The application of the compounds or agents of the present invention to plants or plant materials or their sites includes application by techniques known to those skilled in the art, including but not limited to spraying, coating, impregnation, fumigation, immersion, injection, and powdering. The term "application" means physical or chemical adhesion to a plant or plant part, including impregnation.

[0071] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, the raw materials used are all common commercial products, and their purity level is all analytical grade.

[0072] The room temperature or normal temperature below refers to a temperature of 25±2℃.

[0073] Preparation Example 1: Preparation of Compound 2

[0074] At room temperature, 100 g of the compound shown in 1-1 was added to a 2 L reaction flask, and 1 L of glacial acetic acid was added with stirring. Then, 114 g of ICl was dissolved in 400 mL of glacial acetic acid and added dropwise to the above reaction system over 30 min with stirring. After the addition was complete, the reaction was stirred for about 3 h. After the reaction was complete, the reaction solution was filtered, and the resulting solid was washed with 800 mL of glacial acetic acid and dried to obtain intermediate 1-2.

[0075] Add 95 g of cuprous bromide to a 2 L two-necked flask, add 300 mL of acetonitrile, heat to 65 °C, then add 55 g of tert-butyl nitrite. Dissolve 100 g of intermediate 1-2 in 700 mL of acetonitrile and add it to the flask. After the reaction is complete, evaporate the acetonitrile to dryness, wash with 1 mol / L hydrochloric acid solution, extract with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, and remove excess water to obtain intermediate 1-3.

[0076] 80 g of intermediate 1-3 was added to a 2 L single-necked flask, followed by 1 L of tetrahydrofuran and 24 g of sodium methanethiol. The reaction was allowed to proceed overnight. After the reaction was completed, the solvent was removed, the mixture was washed with water, extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, and column chromatography was performed to obtain intermediate 1-4.

[0077] 43 g of intermediate 1-4 was added to a 1 L flask, followed by 500 mL of tetrahydrofuran and 43 g of 30 wt% methylamine aqueous solution. The reaction was allowed to proceed overnight. After the reaction was completed, the mixture was washed with saturated sodium bicarbonate solution, extracted with ethyl acetate, and the organic phases were combined. The mixture was dried over anhydrous sodium sulfate to obtain intermediate 1-5.

[0078] 42 g of intermediates 1-5 and 4.7 g of [1,1′-bis(diphenylphosphine)ferrocene]palladium(II) dichloride were added to a 1 L two-necked flask. Under a CO atmosphere, 300 mL of DMF and 300 mL of methanol were added, and 26.2 g of triethylamine was added with stirring. The mixture was heated to 90 °C and reacted. After the reaction was completed, the solvent was evaporated, the mixture was washed with water, extracted with ethyl acetate, and the organic phases were combined. The mixture was dried over anhydrous sodium sulfate and the solvent was evaporated to obtain intermediates 1-6.

[0079] 28 g of intermediate 1-6 and 29 g of ammonium chloride were added to a 1 L flask, along with 400 mL of ethanol and 100 mL of water. Then, 24.5 g of iron powder was added, and the mixture was reacted at 80 °C. After the reaction was completed, the iron powder was filtered off, the mixture was washed with ethanol, the filtrate was evaporated to dryness, saturated sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the residue was dehydrated to obtain intermediate 1-7.

[0080] 22 g of intermediate 1-7 was added to a 500 mL flask, followed by 200 mL of dichloromethane and 20 g of triethylamine. Then, 11.5 g of triphosgene was dissolved in 100 mL of dichloromethane and added dropwise to the flask under ice bath conditions. After the addition was complete, the reaction was carried out at room temperature. After the reaction was completed, the solvent was evaporated, and the mixture was washed with 500 mL of water. The mixture was then extracted with dichloromethane, and the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain intermediate 1-8.

[0081] Add 3 g of intermediate 1-8 to a 100 mL round-bottom flask, add 35 mL of DMF, and stir. Then add 5.8 g of Cs₂CO₃ and continue stirring for about 30 min. Next, slowly add 2.5 g of iodomethane dropwise to the reaction system while stirring. After the reaction is complete, add 150 mL of water to the system, and extract the reaction system three times with 50 mL of ethyl acetate each time. Combine the organic layers, dry them with anhydrous sodium sulfate, and pass them by column chromatography to obtain intermediate 1-9.

[0082] 2.5 g of intermediate 1-9 was added to a 100 mL round-bottom flask, followed by 30 mL of dichloromethane. 5 g of m-chloroperoxybenzoic acid was added in portions under ice bath conditions. The reaction was carried out at room temperature. After the reaction was completed, the mixture was washed with saturated sodium sulfite solution and extracted with dichloromethane. The organic phases were combined, washed again with saturated sodium bicarbonate solution, extracted with dichloromethane, and the organic phases were combined. The mixture was dried over anhydrous sodium sulfate and the solvent was evaporated to obtain intermediate 1-10.

[0083] 2.4 g of intermediate 1-10 and 677 mg of lithium hydroxide monohydrate were added to a 100 mL round-bottom flask, along with 20 mL of methanol and 10 mL of water. The mixture was refluxed, and after the reaction was complete, the methanol was removed by rotary evaporation. After cooling to room temperature, a 1 mol / L hydrochloric acid solution was added with stirring to adjust the pH of the system to about 1. A large amount of solid precipitated out, and the intermediate 1-11 was obtained by filtration.

[0084] 500 mg of intermediate 1-11 was added to a 100 mL single-necked flask, followed by 30 mL of THF. 419 mg of SOCl2 was slowly added dropwise at room temperature. After the addition was complete, the mixture was refluxed at 70 °C for approximately 1.5 h, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed. 20 mL of CH2Cl2, 296 mg of cyclohexanedione, and 356 mg of Et3N were added, and the reaction was continued for approximately 0.5 h, monitored by TLC until the acyl chloride disappeared. After the reaction was complete, the mixture was washed once with 25 mL of water, twice with 20 mL of saturated NaHCO3, extracted with dichloromethane, dried over anhydrous Na2SO4, and column filtered to obtain intermediate 1-12.

[0085] 470 mg of intermediate 1-12 was added to a 50 mL round-bottom flask, followed by 20 mL of acetonitrile, 250 mg of Et3N, and 10 mg of acetone cyanohydrin. The reaction was carried out at 50 °C, and TLC was monitored until the reactants disappeared. After the reaction was complete, the acetonitrile was removed, and the mixture was washed with 40 mL of 1 mol / L hydrochloric acid, with the reaction mixture extracted three times each time with 20 mL of dichloromethane. The organic phases were combined and washed three times each time with 10 mL of saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a pale yellow oil. The oil was recrystallized from methanol to give compound 2.

[0086] Preparation Example 2: Preparation of Compound 34

[0087] 3 g of intermediate 1-8 was added to a 100 mL round-bottom flask, followed by 35 mL of DMF. While stirring, 5.8 g of Cs₂CO₃ was added, and the reaction mixture was stirred for approximately 30 min. Then, 3.1 g of benzyl bromide was slowly added dropwise to the reaction system. After the addition was complete, the mixture was stirred overnight at room temperature. After the reaction was complete, 150 mL of water was added to the system, and the reaction mixture was extracted three times with 50 mL of ethyl acetate each time. The organic layers were combined, dried over anhydrous sodium sulfate, and column chromatography was performed to obtain intermediate 1-13.

[0088] Add 3 g of intermediate 1-13 to a 100 mL round-bottom flask, add 30 mL of dichloromethane, and add 6 g of m-chloroperoxybenzoic acid in portions under ice bath conditions. React at room temperature. After the reaction is complete, wash with saturated sodium sulfite solution, extract with dichloromethane, combine the organic phases, wash with saturated sodium bicarbonate solution, extract with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, and evaporate the solvent to obtain intermediate 1-14.

[0089] 2.5 g of intermediate 1-14 and 561 mg of lithium hydroxide monohydrate were added to a 100 mL round-bottom flask, along with 20 mL of methanol and 10 mL of water. The mixture was refluxed, and after the reaction was complete, the methanol was removed by rotary evaporation. After cooling to room temperature, a 1 mol / L hydrochloric acid solution was added with stirring to adjust the pH of the system to about 1. A large amount of solid precipitated out, and the solid was obtained by filtration.

[0090] 500 mg of intermediate 1-15 was added to a 100 mL single-necked flask, followed by 30 mL of THF. 330 mg of SOCl2 was slowly added dropwise at room temperature. After the addition was complete, the mixture was refluxed at 70 °C for approximately 1.5 h, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed. 20 mL of CH2Cl2, 233 mg of cyclohexanedione, and 420 mg of Et3N were added, and the reaction was continued for approximately 0.5 h, monitored by TLC until the acyl chloride disappeared. After the reaction was complete, the mixture was washed once with 25 mL of water, twice with 20 mL of saturated NaHCO3, extracted with dichloromethane, dried over anhydrous Na2SO4, and column filtered to obtain intermediate 1-16.

[0091] 450 mg of intermediate 1-16 was added to a 50 mL round-bottom flask, followed by 20 mL of acetonitrile, 200 mg of Et3N, and 10 mg of acetone cyanohydrin. The reaction was carried out at room temperature, and TLC was monitored until the reactants disappeared. After the reaction was complete, the acetonitrile was removed, and the mixture was washed with 40 mL of 1 mol / L hydrochloric acid, with the reaction mixture extracted three times each time with 20 mL of dichloromethane. The organic phases were combined and washed three times each time with 10 mL of saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a pale yellow oil. The oil was recrystallized from methanol to give compound 34.

[0092] Preparation Example 3: Preparation of Compound 77

[0093] 40 g of intermediate 1-4 was added to a 1 L flask, followed by 500 mL of tetrahydrofuran and 17.25 g of ethylamine. The reaction was allowed to proceed overnight. After the reaction was complete, the mixture was washed with saturated sodium carbonate solution, extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, and dehydrated to obtain intermediate 2-5.

[0094] 41 g of intermediate 2-5 and 4.4 g of [1,1′-bis(diphenylphosphine)ferrocene]palladium(II) dichloride were added to a 1 L two-necked flask. 300 mL of DMF and 300 mL of methanol were added under a carbon monoxide atmosphere. 24.5 g of triethylamine was added with stirring, and the mixture was heated to 90 °C. After the reaction was completed, the solvent was evaporated, the mixture was washed with water, extracted with ethyl acetate, and the organic phases were combined. The mixture was dried over anhydrous sodium sulfate and the solvent was evaporated to obtain intermediate 2-6.

[0095] 26 g of intermediate 2-6 and 25.5 g of ammonium chloride were added to a 1 L flask, along with 400 mL of ethanol and 100 mL of water. Then, 21.5 g of iron powder was added. The mixture was reacted at 80 °C. After the reaction was complete, the iron powder was filtered off, the mixture was washed with ethanol, the filtrate was evaporated to dryness, saturated sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the residue was dehydrated to obtain intermediate 2-7.

[0096] 21.5 g of intermediate 2-7 was added to a 500 mL flask, followed by 200 mL of dichloromethane and 18 g of triethylamine. Then, 10.6 g of triphosgene was dissolved in 100 mL of dichloromethane and added dropwise to the flask under ice bath conditions. After the addition was complete, the reaction was carried out at room temperature. After the reaction was completed, the solvent was evaporated, and the mixture was washed with 500 mL of water and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain intermediate 2-8.

[0097] 3 g of intermediate 2-8 was added to a 100 mL round-bottom flask, followed by 35 mL of DMF. 7.3 g of Cs₂CO₃ was then added with stirring, and the reaction mixture was stirred for approximately 30 min. Next, 3.1 g of 2-iodobutane was slowly added dropwise to the reaction system. After the addition was complete, the mixture was stirred overnight at room temperature. After the reaction was complete, 150 mL of water was added to the system, and the reaction mixture was extracted three times with 50 mL of ethyl acetate each time. The organic layers were combined, dried over anhydrous sodium sulfate, and column chromatography was performed to obtain intermediate 2-9.

[0098] 2.7 g of intermediate 2-9 was added to a 100 mL round-bottom flask, followed by 30 mL of dichloromethane. 5.8 g of m-chloroperoxybenzoic acid was added in portions under ice bath conditions. The reaction was carried out at room temperature. After the reaction was completed, the mixture was washed with saturated sodium sulfite solution and extracted with dichloromethane. The organic phases were combined, washed again with saturated sodium bicarbonate solution, extracted with dichloromethane, and the organic phases were combined. The mixture was dried over anhydrous sodium sulfate and the solvent was evaporated to obtain intermediate 2-10.

[0099] 2.4 g of intermediate 2-10 and 569 mg of lithium hydroxide monohydrate were added to a 100 mL round-bottom flask, along with 20 mL of methanol and 10 mL of water. The mixture was refluxed, and after the reaction was complete, the methanol was removed by rotary evaporation. After cooling to room temperature, a 1 mol / L hydrochloric acid solution was added with stirring to adjust the pH of the system to about 1. A large amount of solid precipitated out, and the intermediate 2-11 was obtained by filtration.

[0100] 500 mg of intermediate 2-11 was added to a 100 mL single-necked flask, followed by 30 mL of THF. 350 mg of SOCl2 was slowly added dropwise at room temperature. After the addition was complete, the mixture was refluxed at 70 °C for approximately 1.5 h, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed. 20 mL of CH2Cl2, 247 mg of cyclohexanedione, and 445 mg of Et3N were added, and the reaction was continued for approximately 0.5 h, monitored by TLC until the acyl chloride disappeared. After the reaction was complete, the mixture was washed once with 25 mL of water, twice with 20 mL of saturated NaHCO3, extracted with dichloromethane, dried over anhydrous Na2SO4, and column filtered to obtain intermediate 2-12.

[0101] 440 mg of intermediate 2-12 was added to a 50 mL round-bottom flask, followed by 20 mL of acetonitrile, 205 mg of Et3N, and 8 mg of acetone cyanohydrin. The reaction was carried out at room temperature for 15 h, and TLC was monitored until the reactants disappeared. After the reaction was complete, the acetonitrile was removed, and the mixture was washed with 40 mL of 1 mol / L hydrochloric acid, with the reaction mixture extracted three times each time with 20 mL of dichloromethane. The organic phases were combined and washed three times each with 10 mL of saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a pale yellow oil. The oil was recrystallized from methanol to give compound 77.

[0102] Preparation Example 4: Preparation of Compound 206

[0103] 57 g of cuprous chloride was added to a 2 L two-necked flask, followed by 300 mL of acetonitrile. The mixture was heated to 65 °C, and then 55 g of tert-butyl nitrite was added. 100 g of intermediate 1-2 was dissolved in 700 mL of acetonitrile and added to the flask. After the reaction was complete, the acetonitrile was evaporated to dryness, and the mixture was washed with 1 mol / L hydrochloric acid solution. The mixture was extracted with dichloromethane, and the organic phases were combined, dried over anhydrous sodium sulfate, and passed through a column to obtain intermediate 3-3.

[0104] 70 g of intermediate 3-3 was added to a 2 L flask, followed by 1 L of tetrahydrofuran and 72 g of 30 wt% methylamine aqueous solution. The reaction was allowed to proceed overnight. After the reaction was completed, the mixture was washed with saturated sodium carbonate solution, extracted with ethyl acetate, and the organic phases were combined. The mixture was then dried over anhydrous sodium sulfate to obtain intermediate 3-4.

[0105] 65 g of intermediate 3-4 and 7.6 g of [1,1′-bis(diphenylphosphine)ferrocene]palladium(II) dichloride were added to a 2 L two-necked flask. Under a carbon monoxide atmosphere, 600 mL of DMF and 600 mL of methanol were added, and 42 g of triethylamine was added with stirring. The mixture was heated to 90 °C and reacted. After the reaction was completed, the solvent was evaporated, the mixture was washed with water, extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain intermediate 3-5.

[0106] 40 g of intermediate 3-5 and 43 g of ammonium chloride were added to a 2 L flask, along with 800 mL of ethanol and 200 mL of water. Then, 36.6 g of iron powder was added, and the mixture was reacted at 80 °C. After the reaction was completed, the iron powder was filtered off, the mixture was washed with ethanol, the filtrate was evaporated to dryness, saturated sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the residue was dehydrated to obtain intermediate 3-6.

[0107] 31 g of intermediate 3-6 was added to a 1 L flask, followed by 400 mL of dichloromethane and 29 g of triethylamine. Then, 17 g of triphosgene was dissolved in 200 mL of dichloromethane and added dropwise to the flask under ice bath conditions. After the addition was complete, the reaction was carried out at room temperature. After the reaction was completed, the solvent was evaporated, and the mixture was washed with 800 mL of water. The mixture was extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain intermediate 3-7.

[0108] 3 g of intermediate 3-7 was added to a 100 mL round-bottom flask, followed by 35 mL of DMF. While stirring, 6.1 g of Cs₂CO₃ was added, and the reaction mixture was stirred for approximately 30 min. Then, 2.7 g of iodomethane was slowly added dropwise to the reaction system, and the reaction was stirred after the addition was complete. After the reaction was complete, 150 mL of water was added to the system, and the reaction mixture was extracted three times with 50 mL of ethyl acetate each time. The organic layers were combined, dried over anhydrous sodium sulfate, and column chromatography was performed to obtain intermediate 3-8.

[0109] 2.5 g of intermediate 3-8 and 824 mg of lithium hydroxide monohydrate were added to a 100 mL round-bottom flask, along with 20 mL of methanol and 10 mL of water. The mixture was refluxed, and after the reaction was complete, the methanol was removed by rotary evaporation. After cooling to room temperature, a 1 mol / L hydrochloric acid solution was added with stirring to adjust the pH of the system to about 1. A large amount of solid precipitated out, and intermediate 3-9 was obtained by filtration.

[0110] 500 mg of intermediate 3-9 was added to a 100 mL single-necked flask, followed by 30 mL of THF. 495 mg of SOCl2 was slowly added dropwise at room temperature. After the addition was complete, the mixture was refluxed at 70 °C for approximately 1.5 h, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed. 20 mL of CH2Cl2, 349 mg of cyclohexanedione, and 420 mg of Et3N were added, and the reaction was continued for approximately 0.5 h, monitored by TLC until the acyl chloride disappeared. After the reaction was complete, the mixture was washed once with 25 mL of water, twice with 10 mL of saturated NaHCO3, extracted with dichloromethane, dried over anhydrous Na2SO4, and column filtered to obtain intermediate 3-10.

[0111] 530 mg of intermediate 3-10 was added to a 50 mL round-bottom flask, followed by 20 mL of acetonitrile, 310 mg of Et3N, and 10 mg of acetone cyanohydrin. The reaction was carried out at 50 °C, and TLC was monitored until the reactants disappeared. After the reaction was complete, the acetonitrile was removed, and the mixture was washed with 40 mL of 1 mol / L hydrochloric acid, with the reaction mixture extracted three times each time with 20 mL of dichloromethane. The organic phases were combined and washed three times each time with 10 mL of saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a pale yellow oil. The oil was recrystallized from methanol to give compound 206.

[0112] Preparation Example 5: Preparation of Compound 273

[0113] 40 g of intermediate 1-3 was added to a 1 L flask, followed by 500 mL of tetrahydrofuran and 32 g of 30 wt% methylamine aqueous solution. The reaction was allowed to proceed overnight. After the reaction was completed, the mixture was washed with saturated sodium carbonate solution, extracted with ethyl acetate, and the organic phases were combined. The mixture was dried over anhydrous sodium sulfate to obtain intermediate 4-4.

[0114] 40 g of intermediate 4-4 and 4.1 g of [1,1′-bis(diphenylphosphine)ferrocene]palladium(II) dichloride were added to a 1 L two-necked flask. 300 mL of DMF and 300 mL of methanol were added under a carbon monoxide atmosphere. 22.6 g of triethylamine was added with stirring, and the mixture was heated to 90 °C. After the reaction was completed, the solvent was evaporated, the mixture was washed with water, extracted with ethyl acetate, and the organic phases were combined. The mixture was dried over anhydrous sodium sulfate and the solvent was evaporated to obtain intermediate 4-5.

[0115] 26 g of intermediate 4-5 and 23.84 g of ammonium chloride were added to a 1 L flask, along with 400 mL of ethanol and 100 mL of water. Then, 20.2 g of iron powder was added, and the mixture was reacted at 80 °C. After the reaction was complete, the iron powder was filtered off, the mixture was washed with ethanol, the filtrate was evaporated to dryness, saturated sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the residue was dehydrated to obtain intermediate 4-6.

[0116] 21.5 g of intermediate 4-6 was added to a 500 mL flask, followed by 200 mL of dichloromethane and 16.8 g of triethylamine. Then, 9.86 g of triphosgene was dissolved in 100 mL of dichloromethane and added dropwise to the flask under ice bath conditions. After the addition was complete, the reaction was carried out at room temperature. After the reaction was completed, the solvent was evaporated, and the mixture was washed with 500 mL of water. The mixture was then extracted with dichloromethane, and the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was evaporated to obtain intermediate 4-7.

[0117] Add 3 g of intermediate 4-7 to a 100 mL round-bottom flask, add 35 mL of DMF, and then add 5.1 g of Cs₂CO₃ while stirring. Continue stirring for about 30 min. Then, slowly add 2 g of bromomethyl methyl ether to the reaction system. After the addition is complete, stir the reaction overnight at room temperature. After the reaction is complete, add 150 mL of water to the system, and extract the reaction system three times with 50 mL of ethyl acetate each time. Combine the organic layers, dry them with anhydrous sodium sulfate, and pass them by column chromatography to obtain intermediate 4-8.

[0118] 2.5 g of intermediate 4-8 and 638 mg of lithium hydroxide monohydrate were added to a 100 mL round-bottom flask, along with 20 mL of methanol and 10 mL of water. The mixture was refluxed, and after the reaction was complete, the methanol was removed by rotary evaporation. After cooling to room temperature, a 1 mol / L hydrochloric acid solution was added with stirring to adjust the pH of the system to about 1. A large amount of solid precipitated out, and intermediate 4-9 was obtained by filtration.

[0119] 500 mg of intermediate 4-9 was added to a 100 mL single-necked flask, followed by 30 mL of THF. 378 mg of SOCl2 was slowly added dropwise at room temperature. After the addition was complete, the mixture was refluxed at 70 °C for approximately 1.5 h, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed. 20 mL of CH2Cl2, 267 mg of cyclohexanedione, and 481 mg of Et3N were added, and the reaction was continued for approximately 0.5 h, monitored by TLC until the acyl chloride disappeared. After the reaction was complete, the mixture was washed once with 25 mL of water, twice with 20 mL of saturated NaHCO3, extracted with dichloromethane, dried over anhydrous Na2SO4, and column filtered to obtain intermediate 4-10.

[0120] 440 mg of intermediate 4-10 was added to a 50 mL round-bottom flask, followed by 20 mL of acetonitrile, 217 mg of Et3N, and 7 mg of acetone cyanohydrin. The reaction was carried out at room temperature for 15 h, and TLC was monitored until the reactants disappeared. After the reaction was complete, the acetonitrile was removed, and the mixture was washed with 40 mL of 1 mol / L hydrochloric acid, with the reaction mixture extracted three times each time with 20 mL of dichloromethane. The organic phases were combined and washed three times each time with 10 mL of saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a pale yellow oil. The oil was recrystallized from methanol to give compound 273.

[0121] Preparation Example 6: Preparation of Compound 334

[0122] Add 3 g of intermediate 1-8 to a 100 mL round-bottom flask, add 35 mL of DMF, and then add 5.8 g of Cs₂CO₃ while stirring. Continue stirring for about 30 min. Then, slowly add 3 g of 1-iodopropane dropwise to the reaction system. After the addition is complete, stir the reaction overnight at room temperature. After the reaction is complete, add 150 mL of water to the system, and extract the reaction system three times with 50 mL of ethyl acetate each time. Combine the organic layers, dry them with anhydrous sodium sulfate, and pass them by column chromatography to obtain intermediate 5-9.

[0123] 2.8 g of intermediate 5-9 was added to a 100 mL round-bottom flask, followed by 30 mL of dichloromethane. 2.4 g of m-chloroperoxybenzoic acid was added in portions under ice bath conditions. The reaction was carried out at room temperature. After the reaction was completed, the mixture was washed with saturated sodium sulfite solution and extracted with dichloromethane. The organic phases were combined, washed again with saturated sodium bicarbonate solution, extracted with dichloromethane, and the organic phases were combined. The mixture was dried over anhydrous sodium sulfate and the solvent was evaporated to obtain intermediate 5-10.

[0124] 2.4 g of intermediate 5-10 and 649 mg of lithium hydroxide monohydrate were added to a 100 mL round-bottom flask, along with 20 mL of methanol and 10 mL of water. The mixture was refluxed, and after the reaction was complete, the methanol was removed by rotary evaporation. After cooling to room temperature, a 1 mol / L hydrochloric acid solution was added with stirring to adjust the pH of the system to about 1. A large amount of solid precipitated out, and the solid was obtained by filtration.

[0125] 500 mg of intermediate 5-11 was added to a 100 mL single-necked flask, followed by 30 mL of THF. 402 mg of SOCl2 was slowly added dropwise at room temperature. After the addition was complete, the mixture was refluxed at 70 °C for approximately 1.5 h, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed. 20 mL of CH2Cl2, 283 mg of cyclohexanedione, and 511 mg of Et3N were added, and the reaction was continued for approximately 0.5 h, monitored by TLC until the acyl chloride disappeared. After the reaction was complete, the mixture was washed once with 25 mL of water, twice with 20 mL of saturated NaHCO3, extracted with dichloromethane, dried over anhydrous Na2SO4, and column filtered to obtain intermediate 5-12.

[0126] 450 mg of intermediate 5-12 was added to a 50 mL round-bottom flask, followed by 20 mL of acetonitrile, 233 mg of Et3N, and 8 mg of acetone cyanohydrin. The reaction was carried out at room temperature for 15 h, and TLC was monitored until the reactants disappeared. After the reaction was complete, the acetonitrile was removed, and the mixture was washed with 40 mL of 1 mol / L hydrochloric acid, with the reaction mixture extracted three times each time with 20 mL of dichloromethane. The organic phases were combined and washed three times each time with 10 mL of saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a pale yellow oil. The oil was recrystallized from methanol to give compound 334.

[0127] Preparation Example 7: Preparation of Compound 346

[0128] 2 g of intermediate 1-9 and 315 mg of lithium hydroxide monohydrate were added to a 100 mL round-bottom flask, along with 20 mL of methanol and 10 mL of water. The mixture was refluxed, and after the reaction was complete, the methanol was removed by rotary evaporation. After cooling to room temperature, a 1 mol / L hydrochloric acid solution was added with stirring to adjust the pH of the system to about 1. A large amount of solid precipitated out, and the solid was obtained by filtration. Intermediate 6-11 was then obtained.

[0129] 500 mg of intermediate 6-11 was added to a 100 mL single-necked flask, followed by 30 mL of THF. 472 mg of SOCl2 was slowly added dropwise at room temperature. After the addition was complete, the mixture was refluxed at 70 °C for approximately 1.5 h, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed. 20 mL of CH2Cl2, 333 mg of cyclohexanedione, and 601 mg of Et3N were added, and the reaction was continued for approximately 0.5 h, monitored by TLC until the acyl chloride disappeared. After the reaction was complete, the mixture was washed once with 25 mL of water, twice with 20 mL of saturated NaHCO3, extracted with dichloromethane, dried over anhydrous Na2SO4, and column filtered to obtain intermediate 6-12.

[0130] 520 mg of intermediate 6-12 was added to a 50 mL round-bottom flask, followed by 20 mL of acetonitrile, 303 mg of Et3N, and 10 mg of acetone cyanohydrin. The reaction was carried out at room temperature for 15 h, and TLC was monitored until the reactants disappeared. After the reaction was complete, the acetonitrile was removed, and the mixture was washed with 40 mL of 1 mol / L hydrochloric acid, with the reaction mixture extracted three times each time with 20 mL of dichloromethane. The organic phases were combined and washed three times each with 10 mL of saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a pale yellow oil. The oil was recrystallized from methanol to give compound 346.

[0131] Preparation Example 8: Preparation of Compound 373

[0132] 500 mg of intermediate 1-11 was added to a 100 mL single-necked flask, followed by 30 mL of THF. 419 mg of SOCl2 was slowly added dropwise at room temperature. After the addition was complete, the mixture was refluxed at 70 °C for approximately 1.5 h, and the reaction was monitored by TLC. After the reaction was complete, the solvent was removed. 20 mL of CH2Cl2, 296 mg of 1,3-dimethyl-5-pyrazolone, and 356 mg of Et3N were added, and the reaction was continued for approximately 0.5 h. TLC was monitored until the acyl chloride disappeared. After the reaction was complete, the mixture was washed once with 25 mL of water, twice with 20 mL of saturated NaHCO3, extracted with dichloromethane, dried over anhydrous Na2SO4, and column filtered to obtain intermediate 7-12.

[0133] 470 mg of intermediate 7-12 was added to a 50 mL round-bottom flask, followed by 20 mL of acetonitrile, 250 mg of Et3N, and 10 mg of acetone cyanohydrin. The reaction was carried out at 50 °C, and TLC was monitored until the reactants disappeared. After the reaction was complete, the acetonitrile was removed, and the mixture was washed with 40 mL of 1 mol / L hydrochloric acid, with the reaction mixture extracted three times each time with 20 mL of dichloromethane. The organic phases were combined and washed three times each time with 10 mL of saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a pale yellow oil. The oil was recrystallized from methanol to give compound 373.

[0134] Preparation Example 9: Preparation of Compound 778

[0135] 200 mg of intermediate I-15 was added to a 50 mL pear-shaped flask and dissolved in 15 mL of ultra-dry acetonitrile. Then, 99 mg of N,N'-carbonyldiimidazole was added, and the mixture was refluxed for 1 h. TLC monitoring was performed after the starting material disappeared. Then, 66 mg of 1-methyl-5-aminotetrazazole and 169 mg of 1,8-diazabicyclo[5.4.0]undec-7-ene were added, and the mixture was refluxed again. TLC was used to monitor the reaction. After the reaction was complete, the acetonitrile in the system was dried, and then 20 mL of 1 mol / L hydrochloric acid solution was added. The mixture was extracted with dichloromethane (3 × 20 mL), and the combined organic phases were dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a pale yellow oil. The oil was recrystallized from methanol to give compound 778.

[0136] Preparation Example 10: Preparation of Compound 1150

[0137] 200 mg of intermediate I-15 was added to a 50 mL pear-shaped flask and dissolved in 15 mL of ultra-dry acetonitrile. Then, 99 mg of N,N'-carbonyldiimidazole was added, and the mixture was refluxed for 1 h. TLC monitoring was performed after the starting material disappeared. Then, 66 mg of 2-amino-5-methyl-1,3,4-oxadiazole and 169 mg of 1,8-diazabicyclo[5.4.0]undec-7-ene were added, and the mixture was refluxed again. TLC was used to monitor the reaction. After the reaction was complete, the acetonitrile in the system was dried, and then 20 mL of 1 mol / L hydrochloric acid solution was added. The mixture was extracted with dichloromethane (3 × 20 mL), and the combined organic phases were dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a pale yellow oil. The oil was recrystallized from methanol to give compound 1150.

[0138] Preparation Example 11: Preparation of Compound 323

[0139] 100.0 g of intermediate 1-2 was dissolved in 500 mL of diethyl disulfide, and 39.7 g of copper powder was added. After the reaction system was heated to 65 °C, 73.1 g of tert-butyl nitrite was slowly added dropwise. After the addition was complete, the reaction continued. The reaction was monitored by TLC until it was complete. After the system was cooled to room temperature, it was filtered, the solvent was evaporated under reduced pressure, water was added, and the mixture was extracted with dichloromethane. The organic phase was dried, concentrated, and purified to obtain intermediate 11-3.

[0140] 26.2 g of intermediate 11-3 was dissolved in 500 mL of tetrahydrofuran, and 3 equivalents of an alcoholic solution of methylamine were added. The mixture was stirred and the reaction was monitored by TLC until the reaction was complete. The solvent was removed, and a saturated sodium bicarbonate solution was added. The mixture was extracted with dichloromethane, and the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to obtain intermediate 11-4.

[0141] 27 g of intermediate 11-4 was weighed and added to a 1 L two-necked flask, followed by 1.8 g of dichloro[9,9-dimethyl-4,5-bis(diphenylphosphine)oxanthracene]palladium(II). Under a carbon monoxide atmosphere, 300 mL of DMF, 300 mL of CH3OH, and 16.2 g of triethylamine were added. After the addition was complete, the system was maintained at 90 °C for reaction. After the reaction was completed by TLC monitoring, the system was depressurized to remove the solvent, and water was added. The mixture was extracted with dichloromethane, and the organic phase was dried and concentrated to obtain intermediate 11-5.

[0142] 21 g of intermediate 11-5 was placed in a 1 L round-bottom flask, 360 mL of glacial acetic acid and 240 mL of water were added, and the reaction system temperature was maintained at 85 °C. Then, 17.4 g of iron powder was added in batches. After the addition was completed, the reaction continued. After the reaction was completed, the mixture was filtered, the filtrate was concentrated, diluted with water, and extracted with ethyl acetate. The organic phase was washed with saturated sodium bicarbonate solution and saturated brine, respectively. The organic phase was then dried and the solvent was removed under reduced pressure to obtain intermediate 11-6.

[0143] 19 g of intermediate 11-6 was dissolved in 200 mL of dichloromethane. 16 g of triethylamine was added under ice bath conditions. Then, 9.4 g of triphosgene was dissolved in 100 mL of dichloromethane and slowly added dropwise to the system. After the addition was complete and the system stabilized, the reaction was moved to room temperature. The reaction was monitored by TLC until it ended. The solvent in the reaction system was evaporated to dryness under reduced pressure. Water was added, and the mixture was extracted with dichloromethane. The organic phases were combined, dried, and concentrated to obtain intermediate 11-7 containing the benzimidazolone structure.

[0144] Weigh 2.1 g of intermediate 11-7 and 5.1 g of cesium carbonate into a 100 mL round-bottom flask, add 30 mL of DMF, stir for 30 min, then add 2.9 g of isobutane iodo. After the reaction is complete, monitor the reaction by TLC, then pour the system into a large amount of water, extract with ethyl acetate, collect the organic phase, concentrate and mix the sample, and then separate the intermediate 11-8 by rapid purification chromatography.

[0145] 1.0 g of intermediate 11-8 was dissolved in 20 mL of glacial acetic acid, 5 equivalents of hydrogen peroxide solution was added at room temperature, and a catalytic amount of sodium tungstate dihydrate was added. The system was heated to 80 °C and the reaction was monitored by TLC. After the reaction was completed, the solvent in the system was evaporated to dryness, water was added, and the mixture was extracted with dichloromethane. The organic phases were combined, dried under reduced pressure to remove the solvent, and intermediate 11-9 was obtained.

[0146] Weigh 1 g of intermediate 11-9 and add it to a 100 mL round-bottom flask. Add 10 mL of tetrahydrofuran and 10 mL of water, then add 237 mg of lithium hydroxide monohydrate. React at room temperature. After the intermediate is completely converted by TLC, evaporate the solvent in the system to dryness. Add 1 mol / L HCl solution to adjust the pH to acidic pH = 2-3 under ice bath. A large amount of solid precipitates in the system. Filter under reduced pressure and dry the filter cake to obtain carboxylic acid intermediate 11-10.

[0147] Weigh 500 mg of intermediate 11-10 into a 100 mL round-bottom flask, add 15 mL of dichloromethane, and add 2 equivalents of oxalyl chloride and a catalytic amount of DMF sequentially under ice bath conditions. After no obvious bubbles are generated, move the mixture to room temperature for reaction. After TLC monitoring to ensure complete conversion of the carboxylic acid intermediate, evaporate the dichloromethane and excess oxalyl chloride under reduced pressure to obtain the acyl chloride compound. In another 100 mL round-bottom flask, dissolve 1.5 equivalents of 1,3-cyclohexanedione in 10 mL of dichloromethane, add 3 equivalents of triethylamine, and then dissolve the aforementioned acyl chloride compound in an appropriate amount of dichloromethane and add it to the above reaction system. After the reaction is complete, add saturated sodium bicarbonate solution, extract with dichloromethane, concentrate the organic phase, mix the sample, and then purify by gradient elution column chromatography to obtain enol ester intermediate 11-11.

[0148] 400 mg of intermediate 11-11 was dissolved in 20 mL of acetonitrile, followed by the addition of 2 equivalents of triethylamine and a catalytic amount of acetone cyanohydrin. The system was placed at 50 °C and reacted until the reaction of the starting material was complete as monitored by TLC. The solvent was removed by vacuum distillation, and the mixture was acidified with 1 mol / L hydrochloric acid. It was then extracted with dichloromethane, and the organic phases were combined, dried, and concentrated to obtain an oily substance. The purified target compound 323 was obtained by recrystallization using diethyl ether and methanol.

[0149] Some compounds of the present invention were prepared using a similar method as described above. Table 5 lists the characterization data of some of the compounds of the present invention.

[0150] Table 5

[0151] Test case Herbicidal activity test (pot method): The test targets were barnyard grass, foxtail grass, crabgrass, amaranth, lamb's quarters, and velvetleaf. Post-emergence foliar spraying was performed: 7 cm inner diameter paper cups were filled with composite soil (garden soil: seedling substrate, 1:2, v / v) to 3 / 4 full, and the weeds were directly sown, covered with 0.2 cm of soil, and left to grow to the 4-5 leaf stage. The compound of this invention was applied at a dosage of 150 g ai / ha (grams per hectare) using an automatic spray tower. After the herbicide solution on the weed leaves dried, the plants were transferred to a greenhouse for cultivation (25°C, 70% humidity), and the results were investigated after 20 days.

[0152] The growth inhibition rate was evaluated by visual inspection, and the rating was based on the conditions shown in Table 6. The test results are shown in Tables 7, 8, 9, 10, 11 and 12.

[0153] Table 6

[0154] Table 7

[0155] Table 8

[0156] Table 9

[0157] Table 10

[0158] Table 11

[0159] Table 12

[0160] The compounds provided by this invention exhibit high herbicidal activity against broadleaf weeds, grass weeds, and sedge weeds. Examples of broadleaf weeds include: *Hedysarum heterotropoides*, *Capsella bursa-pastoris*, *Chenopodium album*, *Abutilon theophrasti*, *Galium affine*, *Veronica persica*, *Stellaria media*, *Amaranthus tricolor*, *Solanum nigrum*, *Phyllostachys edulis*, *Portulaca oleracea*, *Amaranthus retroflexus*, and *Caragana korshinskii*. Grass weeds include: *Barnyardgrass*, *Eleusine indica*, *Setaria viridis*, *Setaria viridis*, *Digitaria sanguinalis*, *Alopecurus japonicus*, *Alopecurus japonicus*, *Oryza sativa*, *Brassica rapa*, *Echinochloa crus-galli*, and *Paspalum notatum*. Sedge weeds include: *Iris tectorum* and *Cyperus difformis*.

[0161] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A compound containing a benzimidazolone structure, characterized in that, The compound has the structure shown in formula (I). ， ， ， In equation (I), R 1 C1-C is H, unsubstituted, or substituted by at least one group in combination A. 12 Alkyl, unsubstituted or substituted by at least one group in combination A, C2-C 12 The alkenyl, unsubstituted or substituted C2-C group of combination A 12 The alkynyl group, unsubstituted or substituted with at least one group from combination A, is a six-membered unsaturated aromatic heterocyclic alkyl group containing 1-3 N atoms as cyclic atoms, or -(CH2). m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 For C1-C 12 Alkyl group; m is an integer from 0 to 6; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a cyano group, or a C1-C1 group. 12 alkoxy groups, -SO2-R 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C6 alkyl groups; R 10 For C1-C 12 Any one of the alkyl groups; the combination B contains C1-C 12 Alkyl, C1-C 12 Alkyl, halogen, nitro, cyano, and C1-C6 alkyl groups substituted with at least one halogen; R 2 For C1-C 12 Any one of alkyl, C3-C6 cycloalkyl, and phenyl groups; X is a halogen, -S(O) n -R x Nitro, cyano, -C(O) n -R x C1-C substituted by at least one halogen 12 Any one of the alkyl groups; n is 0, 1, or 2; R x C1-C that is unsubstituted or substituted by at least one halogen 12 Any one of the alkyl groups; Q is any one of the groups in formula (Q1), formula (Q2), formula (Q3), and formula (Q4); In equation (Q1), R 3 R 4 R 5 R 6 Each is independently selected from H and C1-C6 alkyl groups; In equation (Q2), R 7 Selected from H, C2-C 12 alkynyl group, C2-C 12 alkenyl, -S(O) n -R y -C(O) n -R y ;R y C1-C that is unsubstituted or substituted by at least one halogen 12 Alkyl groups, five- or six-membered unsaturated aromatic heterocyclic alkyl groups containing 0-3 nitrogen atoms as cyclic atoms, or phenyl groups; R 8 Selected from C1-C 12 Alkyl group; R 9 Selected from H, C1-C 12 Alkyl groups, C3-C6 cycloalkyl groups; In equation (Q3), R 10 Selected from C1-C 12 Alkyl groups; In equation (Q4), R 11 Selected from C1-C 12 Alkyl groups.

2. The compound according to claim 1, characterized in that, In equation (I), R 1 C1-C is H, unsubstituted, or substituted by at least one group in combination A. 10 Alkyl, unsubstituted or substituted by at least one group in combination A, C2-C 10 The alkenyl, unsubstituted or substituted C2-C group of combination A 10 The alkynyl group, unsubstituted or substituted with at least one group from combination A, is a six-membered unsaturated aromatic heterocyclic alkyl group containing 1-3 N atoms as cyclic atoms, or -(CH2). m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 For C1-C 10 Alkyl group; m is an integer from 0 to 4; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, C1-C 10 alkoxy groups, -SO2-R 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 For C1-C 10 Any one of the alkyl groups; the combination B contains C1-C 10 Alkyl, C1-C 10 alkoxy, halogen, and nitro groups; R 2 For C1-C 10 Any one of the alkyl groups; X is a halogen, -S(O) n -R x Nitro, cyano, C1-C substituted with at least one halogen 10 Any one of the alkyl groups; n is 0, 1, or 2; R x C1-C that is unsubstituted or substituted by at least one halogen 10 Any one of the alkyl groups; Q is any one of the groups in formula (Q1), formula (Q2), formula (Q3), and formula (Q4); In equation (Q1), R 3 R 4 R 5 R 6 Each is independently selected from H and C1-C4 alkyl groups; In equation (Q2), R 7 Selected from H, C2-C 10 alkynyl group; R 8 and R 9 Each is independently selected from C1-C 10 Alkyl groups; In equation (Q3), R 10 Selected from C1-C 10 Alkyl groups; In equation (Q4), R 11 Selected from C1-C 12 Alkyl groups; Preferably, In equation (I), R 1 The following are unsubstituted C1-C6 alkyl groups, unsubstituted C2-C6 alkenyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted six-membered unsaturated aromatic heterocyclic alkyl groups containing 1-2 N atoms as cyclizing atoms, or -(CH2) substituted by H, unsubstituted or substituted by at least one group in combination A. m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 It is a C1-C6 alkyl group; m is an integer from 0 to 3; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a C1-C6 alkoxy group, or -SO2-R. 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 It is any one of C1-C6 alkyl groups; the combination B contains C1-C6 alkyl groups, C1-C6 alkoxy groups, halogens and nitro groups; R 2 It is any one of the alkyl groups from C1 to C6; X is a halogen, -S(O) n -R x Any one of C1-C6 alkyl groups substituted with at least one halogen; n is 0, 1, or 2; R x It is any one of the alkyl groups from C1 to C6; Q is any one of the groups in formula (Q1), formula (Q2), formula (Q3), and formula (Q4); In equation (Q1), R 3 R 4 R 5 R 6 Each is independently selected from H, C1-C3 alkyl groups; In equation (Q2), R 7 Selected from H, C2-C6 alkynyl groups; R 8 and R 9 Each alkyl group is independently selected from C1-C6; In equation (Q3), R 10 Alkyl groups selected from C1-C6; In equation (Q4), R 11 Alkyl groups selected from C1-C6.

3. The compound according to claim 1 or 2, characterized in that, In equation (I), R 1 The following are unsubstituted C1-C6 alkyl groups, unsubstituted C2-C6 alkenyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted six-membered unsaturated aromatic heterocyclic alkyl groups containing 1-2 N atoms as cyclizing atoms, or -(CH2) substituted by H, unsubstituted or substituted by at least one group in combination A. m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 It is a C1-C6 alkyl group; m is an integer from 0 to 3; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a C1-C6 alkoxy group, or -SO2-R. 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 It is any one of C1-C6 alkyl groups; the combination B contains C1-C6 alkyl groups, C1-C6 alkoxy groups, halogens and nitro groups; R 2 It is any one of the alkyl groups from C1 to C6; X can be F, Cl, Br, or -S(O). n -R x Any one of C1-C6 alkyl groups substituted with at least one halogen; n is 0, 1, or 2; R x It is any one of C1-C4 alkyl groups; Q is the group represented by formula (Q1); in formula (Q1), R 3 R 4 R 5 R 6 Each is independently selected from H, methyl, ethyl, n-propyl, and isopropyl; Preferably, The compound shown in formula (I) has the structure shown in formula (I-Q1). Formula (I-Q1), In equation (I-Q1), R 3 R 4 R 5 R 6 Both are H; R 1 R 2 The definitions of X and X are shown in Table 1; Table 1 。 4. The compound according to claim 1 or 2, characterized in that, In equation (I), R 1 The following are unsubstituted C1-C6 alkyl groups, unsubstituted C2-C6 alkenyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted six-membered unsaturated aromatic heterocyclic alkyl groups containing 1-2 N atoms as cyclizing atoms, or -(CH2) substituted by H, unsubstituted or substituted by at least one group in combination A. m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 It is a C1-C6 alkyl group; m is an integer from 0 to 3; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a C1-C6 alkoxy group, or -SO2-R. 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 It is any one of C1-C6 alkyl groups; the combination B contains C1-C6 alkyl groups, C1-C6 alkoxy groups, halogens and nitro groups; R 2 It is any one of the alkyl groups from C1 to C6; X can be F, Cl, Br, or -S(O). n -R x Any one of C1-C6 alkyl groups substituted with at least one halogen; n is 0, 1, or 2; R x It is any one of C1-C4 alkyl groups; Q is the group represented by formula (Q2); in formula (Q2), R 7 Selected from H, C2-C4 alkynyl groups; R 8 and R 9 Each is independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl; Preferably, The compound shown in formula (I) has the structure shown in formula (I-Q2). Formula (I-Q2) In equation (I-Q2), R 8 and R 9 All are methyl; R 1 R 2 R 7 The definitions of X and X are shown in Table 2; Table 2 。 5. The compound according to claim 1 or 2, characterized in that, In equation (I), R 1 The following are unsubstituted C1-C6 alkyl groups, unsubstituted C2-C6 alkenyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted six-membered unsaturated aromatic heterocyclic alkyl groups containing 1-2 N atoms as cyclizing atoms, or -(CH2) substituted by H, unsubstituted or substituted by at least one group in combination A. m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 It is a C1-C6 alkyl group; m is an integer from 0 to 3; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a C1-C6 alkoxy group, or -SO2-R. 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 It is any one of C1-C6 alkyl groups; the combination B contains C1-C6 alkyl groups, C1-C6 alkoxy groups, halogens and nitro groups; R 2 It is any one of the alkyl groups from C1 to C6; X can be F, Cl, Br, or -S(O). n -R x Any one of C1-C6 alkyl groups substituted with at least one halogen; n is 0, 1, or 2; R x It is any one of C1-C4 alkyl groups; Q is the group represented by formula (Q3); in formula (Q3), R 10 Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl; Preferably, The compound shown in formula (I) has the structure shown in formula (I-Q3). Formula (I-Q3), In equation (I-Q3), R 10 Methyl; R 1 R 2 The definitions of X and X are shown in Table 3; Table 3 。 6. The compound according to claim 1 or 2, characterized in that, In equation (I), R 1 The following are unsubstituted C1-C6 alkyl groups, unsubstituted C2-C6 alkenyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted C2-C6 alkynyl groups, unsubstituted six-membered unsaturated aromatic heterocyclic alkyl groups containing 1-2 N atoms as cyclizing atoms, or -(CH2) substituted by H, unsubstituted or substituted by at least one group in combination A. m -R 11 -(CH2) m -COO-R 12 Any one of them; R 11 R is an unsubstituted phenyl group or a phenyl group substituted by at least one group in combination B; 12 It is a C1-C6 alkyl group; m is an integer from 0 to 3; the heteroatom is selected from at least one of N, O, and S; the combination A contains a halogen, a C1-C6 alkoxy group, or -SO2-R. 10 , C2-C6 saturated cycloalkyl groups with or without heteroatoms; unsubstituted or C2-C6 unsaturated aromatic cycloalkyl groups containing heteroatoms, substituted with C1-C4 alkyl groups; R 10 It is any one of C1-C6 alkyl groups; the combination B contains C1-C6 alkyl groups, C1-C6 alkoxy groups, halogens and nitro groups; R 2 It is any one of the alkyl groups from C1 to C6; X can be F, Cl, Br, or -S(O). n -R x Any one of C1-C6 alkyl groups substituted with at least one halogen; n is 0, 1, or 2; R x It is any one of C1-C4 alkyl groups; Q is the group represented by formula (Q4); in formula (Q4), R 11 Selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl; Preferably, The compound shown in formula (I) has the structure shown in formula (I-Q4). Formula (I-Q4) In equation (I-Q4), R 11 Methyl; R 1 R 2 The definitions of X and X are shown in Table 4; Table 4 。 7. The compound according to claim 1 or 2, characterized in that, The compound shown in formula (I) is selected from any one of compound 1 to compound 1487.

8. The use of the compound containing the benzimidazole structure according to any one of claims 1-7 in weed control; Preferably, The weeds include broadleaf weeds, grass weeds, and sedge weeds; Preferably, The broadleaf weeds are selected from at least one of the following: shepherd's purse, shepherd's purse, lambsquarters, velvetleaf, cleavers, speedwell, chickweed, amaranth, black nightshade, lantern grass, purslane, retroflexus, and carp intestines; And / or, the grass weeds are selected from at least one of barnyard grass, goosegrass, golden foxtail grass, foxtail grass, crabgrass, wild oat, Japanese wild oat, jointed barley, wild oat, wild oat, barnyard grass, and double-spike barnyard grass; And / or, the sedges are selected from at least one of Cyperus rotundus and Cyperus heterophylla.

9. A herbicide, characterized in that, The herbicide contains an effective amount of the compound with the benzimidazole structure as described in any one of claims 1-7 for controlling weeds.

10. The herbicide according to claim 9, characterized in that, This herbicide also contains pesticide formulation excipients; And / or, the pesticide formulation excipients are selected from at least one of solvents, emulsifiers, dispersants, wetting agents, stabilizers, thickeners, antifreeze agents, preservatives, fillers, colorants, and defoamers; Preferably, The herbicide formulation is selected from at least one of the following: wettable powder, water-dispersible granules, emulsifiable concentrate, suspension concentrate, aqueous solution, granules, soluble powder, microcapsule suspension, oil suspension, water emulsion, effervescent tablets, and aerosol.

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