Benzo-fused polycyclic compound and use thereof, and HPPD-inhibiting herbicide
By developing benzo[a]polycyclic compounds as HPPD-inhibiting herbicides, the problem of poor control of resistant weeds in existing technologies has been solved, achieving efficient weed control and improved safety for crops such as rice and wheat.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- HUAZHONG NORMAL UNIV
- Filing Date
- 2025-12-11
- Publication Date
- 2026-06-18
AI Technical Summary
Existing HPPD herbicides are not very effective in controlling resistant weeds in wheat fields and other crop fields, and the large amount of herbicide required leads to significant residue problems, preventing them from fully realizing their advantages.
A benzo[a]polycyclic compound is provided as an HPPD-inhibiting herbicide with excellent herbicidal activity, effective against major crops such as rice and wheat as well as resistant weeds, and safe for non-target crops.
It achieves efficient control of resistant weeds, reduces the toxicity risk to non-target crops, and improves the safety and efficiency of herbicide use.
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Figure CN2025141926_18062026_PF_FP_ABST
Abstract
Description
A benzo[a]polycyclic compound and its applications; an HPPD-inhibiting herbicide
[0001] Cross-reference to related applications
[0002] This application claims the benefit of Chinese patent application No. 202411817375.7, filed on December 11, 2024, the contents of which are incorporated herein by reference. Technical Field
[0003] This invention relates to the field of pesticides, specifically to a benzo[a]polycyclic compound and its application, and an HPPD-inhibiting herbicide. Background Technology
[0004] Chemical herbicides play an irreplaceable role in weed control in modern agriculture.
[0005] With the continued large-scale use of chemical herbicides, the types of resistant weeds are constantly increasing, and the affected area and severity are also continuously worsening. 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors have been discovered and used for over 30 years, with only three reported cases of resistance worldwide, making them highly suitable for integrated management of resistant weeds.
[0006] HPPD, a key enzyme in plants, participates in the plant's tyrosine metabolism pathway. It catalyzes the conversion of p-hydroxyphenylpyruvic acid (HPPA) to homogentisic acid (HGA), which is further metabolized in plants to produce plastoquinone and tocopherol. Plastoquinone acts as an electron acceptor in carotenoid biosynthesis and electron transport during photosynthesis. When HPPD is inhibited, carotenoid biosynthesis is hindered, photosynthesis is disrupted, and ultimately, plant bleaching or even death occurs.
[0007] Currently, the vast majority of commercial HPPD herbicides are only suitable for controlling weeds in corn fields, with only a few exceptions for use in rice, wheat, and other crop fields. However, these applications require large amounts of herbicides, resulting in significant residue problems. This prevents existing HPPD herbicides from fully utilizing their advantages in controlling resistant weeds such as those found in wheat fields.
[0008] Therefore, developing novel, highly efficient HPPD herbicides with novel structures and safety for specific crops is one of the important means to solve the problem of frequent weed resistance in major crop fields, and it has huge market value. Summary of the Invention
[0009] The purpose of this invention is to provide a benzo[a]polycyclic compound with the potential to become a novel, highly efficient HPPD-inhibiting herbicide.
[0010] To achieve the above objectives, a first aspect of the present invention provides a benzo[a]polycyclic compound or an agriculturally chemically acceptable salt, hydrate, solvate, or an enantiomer or optically active derivative thereof, the compound having the structure shown in formula (I):
[0011] In formula (I), Q is a group represented by formula (Q1) or formula (Q2);
[0012] R 1 For H, C 1-30 alkyl, C 1-30 alkoxy, halogen, nitro, C substituted with at least one halogen 1-24 Alkyl or -S(O)2-R1; R1 is C 1-24 Alkyl groups;
[0013] R 2 C is H, unsubstituted, or substituted by at least one group in combination 2A. 1-30 alkyl, unsubstituted or substituted C groups of at least one of the groups in combination 2A 1-30 alkoxy, C 2-24 alkenyl, C 2-24 alkenyloxy group, unsubstituted or R2-substituted C 2-24 alkynyl, unsubstituted or R2-substituted C 2-24 alkynyloxy group, unsubstituted or derived from R 24 Substituted phenyl, unsubstituted or derived from R 24 Substituted phenyloxy, C 3-8 Cycloalkyl groups or 3-8 membered unsaturated heterocycloalkyl groups containing at least one type A heteroatom; combination 2A contains halogen, C 1-24 alkoxy, C 1-24 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 -N(R) 22 (R) 23 ), cyano, -Si(R) 21 3、-C(O)-R 22 -COO-R 22 -CO-N(R) 22 (R) 23 C 3-8 cycloalkyl, unsubstituted or derived from R 25 Substituted 3-8 member saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom, unsubstituted or composed of at least one R 24 Substituted phenyl; R2 is selected from -Si(R 21 )3; 3 R 21 Each is independently selected from C 1-12Alkyl group; R 24 Selected from halogens, C 1-24 alkyl, C 1-24 alkoxy, nitro, cyano, C groups substituted with at least one halogen 1-24 Alkyl groups, C substituted with at least one halogen 1-24 alkoxy, C 1-24 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 At least one of the following; Class A heteroatoms include N, O, and S; R 22 and R 23 Each is independently selected from H and C. 1-24 Any one of alkyl and benzyl groups; R 25 Selected from C 3-8 cycloalkyl, unsubstituted or C substituted with at least one halogen 1-12 At least one of the alkyl groups;
[0014] R 3 Selected from H, C 1-24 Alkyl groups, C substituted with at least one halogen 1-24 Alkyl groups, C3 substituted with R3 1-24 R3 is selected from any one of alkyl or phenyl groups; R3 is selected from at least one of -S-R1, -SO-R1, -SO2-R1, and phenyl groups.
[0015] Or, R 2 and R 3 They can cyclize together to form saturated or unsaturated 5-7 membered rings;
[0016] R 4 Selected from H, C 1-24 Any one of the alkyl groups;
[0017] R 5 Selected from H, C 1-24 Alkyl groups, C substituted with at least one halogen 1-24 Alkyl groups, C substituted with R5 1-24 alkyl, C 3-8 cycloalkyl, C 2-24 alkenyl, C 2-24 Any one of the alkynyl groups; R5 is -O-R1 or phenyl;
[0018] n is 0, 1, or 2;
[0019] In equation (Q1), x R 6 Each is independently selected from H and C. 1-12 Alkyl groups, where x is an integer from 1 to 6;
[0020] In equation (Q2), R 7 and R8 Each is independently selected from H and C. 1-24 alkyl, C 3-8 cycloalkyl, phenyl-substituted C 7-24 Alkyl groups;
[0021] R 9 C selected from H, unsubstituted or substituted by at least one group from combination 9A 1-24 alkyl, C 2-24 alkenyl, C 2-24 alkynyl group, -C(R) 91 (R) 92 )-OC(O)-OR 93 -C(R) 91 (R) 92 )-OC(O)-SR 93 -C(R) 91 (R) 92 )-OC(O)-N(R 93 (R) 94 ), -C(R 91 (R) 92 )-C(O)-R 93 -C(O)-R 93 -COO-R 93 -C(O)-SR 93 -C(S)-OR 93 -C(O)-N(R) 93 (R) 94 -C(S)-N(R) 93 (R) 94 -S(O)2-R 93 -S(O)2-N(R) 93 (R) 94 -P(O)(OR) 93 (OR) 94 Combination 9A contains halogens and C. 1-24 alkoxy, cyano, phenyl, or 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one class A heteroatom; R 91 and R 92 Each is independently selected from H and C. 1-24 Alkyl groups; or R 91 and R 92 Together they form 3-6 saturated rings; R 93 C selected from unsubstituted or substituted groups of at least one of the groups in combination 9A 1-24 alkyl, C 3-8 cycloalkyl, C 2-24 alkenyl, unsubstituted or derived from R 95Substituted phenyl groups, 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom; R 94 Selected from H, C 1-12 Alkyl groups; or R 93 and R 94 Together they cyclize to form a 3-8 membered saturated or unsaturated heterocyclic group containing at least one type A heteroatom; R 95 Selected from halogens, C 1-12 alkyl, C 1-12 alkoxy groups.
[0022] The second aspect of the present invention provides the application of the aforementioned benzo[a]polycyclic compound or its agriculturally chemically acceptable salt, hydrate, solvate, or its enantiomer or optically active derivative as an HPPD inhibitor in the control of weeds.
[0023] A third aspect of the present invention provides an HPPD-inhibiting herbicide containing an effective amount of active ingredient for weed control, wherein the active ingredient includes any one of the aforementioned benzo[a]polycyclic compound or its agriculturally chemically acceptable salt, hydrate, solvate, or its enantiomer or optically active derivative.
[0024] The compound containing a benzo[a] polycyclic ring structure provided by this invention has excellent herbicidal activity against weeds, especially resistant weeds, in major crops such as rice and wheat, as well as some important economic crops, and has good safety against non-target crops. Detailed Implementation
[0025] 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.
[0026] The term "halogen," whether used alone or in compound words (such as "halogen-substituted C"), 1-8 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.) 1-8Taking "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.
[0027] Used alone or in compound words (e.g., "C") 1-30 The term "alkyl" as used in the context of "alkyl groups" 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, etc. 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. In particular, C 1-30 The alkyl group indicates an alkyl group with a total number of carbon atoms ranging from 1 to 30, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30. "C 1-10 Alkyl" "C" 1~8 Alkyl", C 1~6 Alkyl", C 1~3 Alkyl groups have similar definitions, differing only in the total number of carbon atoms.
[0028] 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 group includes 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 various isomers. This definition also applies to alkoxy groups that are part of a complex substituent, such as haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere. In particular, C... 1-30 The alkoxy group represents an alkoxy group with a total number of carbon atoms ranging from 1 to 30, where the oxygen atom is attached to the parent nucleus. Examples of the total number of carbon atoms are 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, and 30. "C 1~8 Alkoxy, C 1~6 Alkoxy, C 1~3 Alkoxy groups have similar definitions, differing only in the total number of carbon atoms. 1-24 "alkylthio" has the same properties as "C". 1-24 The definition is similar to that of "alkoxy group", the difference being that "C 1-24 The alkylthio group is connected to the parent nucleus structure through the S atom, while the C group is connected through the S atom. 1-24 The alkoxy group is connected to the parent nucleus structure through an oxygen atom.
[0029] "C substituted by at least one halogen" 1-24 "Halogenated alkyl" indicates "C 1-24 At least one H atom in the alkyl group is substituted with a halogen, and the substituted halogen can be one or more. Examples include trifluoromethyl and trifluoroethyl. A C atom substituted with at least one halogen... 1~8 "Halogenated alkyl", "C substituted with at least one halogen" 1~6 "Halogenated alkyl", "C substituted with at least one halogen" 1~3 "Halogenated alkyl" and the like have similar definitions, differing only in the total number of carbon atoms.
[0030] "C that is unsubstituted or substituted by at least one group in combination 2A"1-30 "alkyl" indicates C 1-30 The alkyl group may contain at least one substituent from combination 2A, or it may not contain any substituents; if it contains at least one substituent from combination 2A, there are no particular requirements regarding the specific substitution position of the substituent, and it can be any position that can be substituted. "Unsubstituted or substituted C..." 1-30 The alkoxy group has a similar interpretation.
[0031] 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. More specifically, "C 2-24 "Alkenyl" represents C 2-24The hydrocarbon group contains at least one unsaturated carbon-carbon double bond, and there is no particular limitation on the specific position of the unsaturated carbon-carbon double bond. "C 2~8 "alkenyl", "C" 2~6 "alkenyl", "C" 2~3 "Alkenyl" and similar terms have similar definitions, differing only in the total number of carbon atoms.
[0032] “C 2-24 The alkenyloxy group has the same properties as "C". 2-24 The definition is similar to that of "alkenyl", the difference being that "C" 2-24 "Alkenyloxy group" is in "C 2-24 It is based on the "alkenyl" group, with an O atom attached, and is connected to the parent nucleus structure through the O atom.
[0033] 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. More specifically, C 2-24 The alkynyl group represents C 2-24 The hydrocarbon group contains at least one unsaturated carbon-carbon triple bond, and there is no particular limitation on the specific position of the unsaturated carbon-carbon triple bond. For example, propargyl, etc. "C 2~8 "Alkyne", "C" 2~6 "Alkyne", "C" 2~3 "Alkyne" and similar terms have similar definitions, differing only in the total number of carbon atoms. "Unsubstituted or R2-substituted C" 2-24 "Alkyne group" indicates that in C 2-24The alkynyl group may or may not have an R2 substituent; if an R2 substituent is present, there are no special requirements on the specific substitution position of the substituent, and it can be any position that can be substituted.
[0034] “C 2-24 The alkynyloxy group has the same properties as "C". 2-24 The definition is similar to that of "alkynyl group", the difference being that "C 2-24 "The alkynyl oxygen group" is in "C 2-24 It is based on the "acetylation group" and attaches an O atom, which is then connected to the parent nucleus structure.
[0035] "Phenoxy group" means that an O atom is attached to the "phenyl" group and connected to the parent nucleus structure through the O atom; for example, if there are no substituents on the "phenyl" group, then the phenoxy group is a phenol group.
[0036] “C 3-8 "Cycloalkyl" refers to a cycloalkyl group with a total number of carbon atoms of 3 to 8, and all cyclic atoms are carbon atoms. For example, it can be a cycloalkyl group with a total number of carbon atoms of 3, 4, 5, 6, 7, or 8, and the "C" is... 3~8 The cycloalkyl group can be directly attached to the parent nucleus at any position. Examples include cyclopropyl, cyclobutyl, and cyclopentyl. 3~6 "Cycloalkyl" and similar terms have similar definitions, differing only in the total number of carbon atoms.
[0037] "A 3-8 membered unsaturated heterocyclic alkyl group containing at least one type A heteroatom" means that the cycloalkyl group has 3, 4, 5, 6, 7, or 8 cyclic atoms, and contains at least one type A heteroatom as a cyclic atom. This group is unsaturated, and the carbon atom in the cyclic atom is connected to the parent nucleus. "Unsaturated heterocyclic group" has a similar definition, except that the heteroatom in the cyclic atom of the "unsaturated heterocyclic group" is connected to the parent nucleus.
[0038] In the structural formulas of the compounds provided in this invention, solid lines not connected to specific sites in the parent nucleus represent bonds that can bind to any site on the corresponding ring of the parent nucleus. Wavy lines in the structural formulas representing functional groups represent sites connected to the parent nucleus.
[0039] As previously stated, a first aspect of the present invention provides a benzo[a] polycyclic compound or an agriculturally chemically acceptable salt, hydrate, solvate, or an enantiomer or optically active derivative thereof, having the structure shown in formula (I).
[0040] In a preferred embodiment, in formula (I), Q is a group represented by formula (Q1) or formula (Q2):
[0041] R 1For H, C 1-12 alkyl, C 1-12 alkoxy, halogen, nitro, C substituted with at least one halogen 1-12 Alkyl or -S(O)2-R1; R1 is C 1-12 Alkyl groups;
[0042] R 2 C is H, unsubstituted, or substituted by at least one group in combination 2A. 1-12 alkyl, unsubstituted or substituted C groups of at least one of the groups in combination 2A 1-12 alkoxy, C 2-12 alkenyl, C 2-12 alkenyloxy group, unsubstituted or R2-substituted C 2-12 alkynyl, unsubstituted or R2-substituted C 2-12 alkynyloxy group, unsubstituted or derived from R 24 Substituted phenyl, unsubstituted or derived from R 24 Substituted phenyloxy, C 3-8 Cycloalkyl groups or 3-8 membered unsaturated heterocycloalkyl groups containing at least one type A heteroatom; combination 2A contains halogen, C 1-12 alkoxy, C 1-12 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 -N(R) 22 (R) 23 ), cyano, -Si(R) 21 3、-C(O)-R 22 -COO-R 22 -CO-N(R) 22 (R) 23 C 3-8 cycloalkyl, unsubstituted or derived from R 25 Substituted 3-8 member saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom, unsubstituted or composed of at least one R 24 Substituted phenyl; R2 is selected from -Si(R 21 )3; 3 R 21 Each is independently selected from C 1-6 Alkyl group; R 24 Selected from halogens, C 1-6 alkyl, C 1-6 alkoxy, nitro, cyano, C groups substituted with at least one halogen 1-6 Alkyl groups, C substituted with at least one halogen 1-6 alkoxy, C 1-6 alkylthio groups, -S(O)-R 22 -S(O)2-R 22At least one of the following; Class A heteroatoms include N, O, and S; R 22 and R 23 Each is independently selected from H and C. 1-6 Any one of alkyl and benzyl groups; R 25 Selected from C 1-6 alkyl, C 3-8 cycloalkyl groups, C substituted with at least one halogen 1-6 At least one of the alkyl groups;
[0043] R 3 Selected from H, C 1-6 Alkyl groups, C substituted with at least one halogen 1-6 Alkyl groups, C3 substituted with R3 1-6 R3 is selected from any one of alkyl or phenyl groups; R3 is selected from at least one of -S-R1, -SO-R1, -SO2-R1, and phenyl groups.
[0044] Or, R 2 and R 3 They can cyclize together to form saturated or unsaturated 5-7 membered rings;
[0045] R 4 Selected from H, C 1-6 Any one of the alkyl groups;
[0046] R 5 Selected from H, C 1-12 Alkyl groups, C substituted with at least one halogen 1-12 Alkyl groups, C substituted with R5 1-6 alkyl, C 3-8 cycloalkyl, C 2-12 alkenyl, C 2-12 Any one of the alkynyl groups; R5 is -O-R1 or phenyl;
[0047] n is 0, 1, or 2;
[0048] In equation (Q1), x R 6 Each is independently selected from H and C. 1-6 Alkyl groups, where x is an integer from 1 to 6;
[0049] In equation (Q2), R 7 and R 8 Each is independently selected from H and C. 1-12 alkyl, C 3-8 cycloalkyl, phenyl-substituted C 7-12 Alkyl groups;
[0050] R 9 C selected from H, unsubstituted or substituted by at least one group from combination 9A 1-12 alkyl, C2-12 alkenyl, C 2-12 alkynyl group, -C(R) 91 (R) 92 )-OC(O)-OR 93 -C(R) 91 (R) 92 )-OC(O)-SR 93 -C(R) 91 (R) 92 )-OC(O)-N(R 93 (R) 94 ), -C(R 91 (R) 92 )-C(O)-R 93 -C(O)-R 93 -COO-R 93 -C(O)-SR 93 -C(S)-OR 93 -C(O)-N(R) 93 (R) 94 -C(S)-N(R) 93 (R) 94 -S(O)2-R 93 -S(O)2-N(R) 93 (R) 94 -P(O)(OR) 93 (OR) 94 Combination 9A contains halogens and C. 1-12 alkoxy, cyano, phenyl, or 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one class A heteroatom; R 91 and R 92 Each is independently selected from H and C. 1-6 Alkyl groups; or R 91 and R 92 Together they form 3-6 saturated rings; R 93 C selected from unsubstituted or substituted groups of at least one of the groups in combination 9A 1-12 alkyl, C 3-8 cycloalkyl, C 2-12 alkenyl, unsubstituted or derived from R 95 Substituted phenyl groups, 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom; R 94 Selected from H, C 1-6 Alkyl groups; or R 93 and R 94 Together they cyclize to form a 3-8 membered saturated or unsaturated heterocyclic group containing at least one type A heteroatom; R 95 Selected from halogens, C 1-6 alkyl, C1-6 alkoxy groups.
[0051] According to the preferred embodiment 1, in formula (I), Q is the group represented by formula (Q1):
[0052] R 1 For H, C 1-12 alkyl, C 1-12 alkoxy, halogen, nitro, C substituted with at least one halogen 1-12 Alkyl or -S(O)2-R1; R1 is C 1-12 Alkyl groups;
[0053] R 2 C is H, unsubstituted, or substituted by at least one group in combination 2A. 1-12 alkyl, unsubstituted or substituted C groups of at least one of the groups in combination 2A 1-12 alkoxy, C 2-12 alkenyl, C 2-12 alkenyloxy group, unsubstituted or R2-substituted C 2-12 alkynyl, unsubstituted or R2-substituted C 2-12 alkynyloxy group, unsubstituted or derived from R 24 Substituted phenyl, unsubstituted or derived from R 24 Substituted phenyloxy, C 3-8 Cycloalkyl groups or 3-8 membered unsaturated heterocycloalkyl groups containing at least one type A heteroatom; combination 2A contains halogen, C 1-12 alkoxy, C 1-12 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 -N(R) 22 (R) 23 ), cyano, -Si(R) 21 3、-C(O)-R 22 -COO-R 22 -CO-N(R) 22 (R) 23 C 3-8 cycloalkyl, unsubstituted or derived from R 25 Substituted 3-8 member saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom, unsubstituted or composed of at least one R 24 Substituted phenyl; R2 is selected from -Si(R 21 )3; 3 R 21 Each is independently selected from C 1-6 Alkyl group; R 24 Selected from halogens, C 1-6 alkyl, C 1-6 alkoxy, nitro, cyano, C groups substituted with at least one halogen1-6 Alkyl groups, C substituted with at least one halogen 1-6 alkoxy, C 1-6 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 At least one of the following; Class A heteroatoms include N, O, and S; R 22 and R 23 Each is independently selected from H and C. 1-6 Any one of alkyl and benzyl groups; R 25 Selected from C 1-6 alkyl, C 3-8 cycloalkyl groups, C substituted with at least one halogen 1-6 At least one of the alkyl groups;
[0054] R 3 Selected from H, C 1-6 Alkyl groups, C substituted with at least one halogen 1-6 Alkyl groups, C3 substituted with R3 1-6 R3 is selected from any one of alkyl or phenyl groups; R3 is selected from at least one of -S-R1, -SO-R1, -SO2-R1, and phenyl groups.
[0055] Or, R 2 and R 3 They can cyclize together to form saturated or unsaturated 5-7 membered rings;
[0056] R 4 Selected from H, C 1-3 Any one of the alkyl groups;
[0057] R 5 Selected from H, C 1-12 Alkyl groups, C substituted with at least one halogen 1-12 Alkyl groups, C substituted with R5 1-6 alkyl, C 3-8 cycloalkyl, C 2-12 alkenyl, C 2-12 Any one of the alkynyl groups; R5 is -O-R1 or phenyl;
[0058] n is 0, 1, or 2.
[0059] In a preferred embodiment 1, more preferably, in formula (I), Q is a group represented by formula (Q1), and R in formula (Q1) 6 All are H; and the compound represented by formula (I) is selected from any one of the following:
[0060] I.1: R 1 R 5 Both are CH3, R 2 R3 R 4 All are H, and n is 0;
[0061] I.2: R 1 R 2 Both are CH3, R 3 R 4 R 5 All are H, and n is 0;
[0062] I.3: R 1 R 2 R 5 Both are CH3, R 3 R 4 All are H, and n is 0;
[0063] I.8:R 1 R 2 Both are CH3, R 3 R 4 Both are H, R 5 The form is CH2CH2F, and n is 0;
[0064] I.10: R 1 R 2 Both are CH3, R 3 R 4 Both are H, R 5 For CH2CH=CH2, n is 0;
[0065] I.11: R 1 R 2 Both are CH3, R 3 R 4 Both are H, R 5 For CH2C≡CH, n is 0;
[0066] I.13: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CH3, and n is 0;
[0067] I.14: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH3, and n is 0;
[0068] I.15: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R2 The expression is CH2CH2CH2CH3, and n is 0;
[0069] I.16: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH2CH2CH3, and n is 0;
[0070] I.17: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH(CH3)CH2CH3, and n is 0;
[0071] I.18: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH(CH3)2, and n is 0;
[0072] I.19: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is C(CH3)3, and n is 0;
[0073] I.22: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH=CH2, n is 0;
[0074] I.23: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2C(CH3)=CH2, and n is 0;
[0075] I.25: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH=CH2, and n is 0;
[0076] I.26: R 1 R 5Both are CH3, R 3 R 4 Both are H, R 2 For CH2C≡CH, n is 0;
[0077] I.27: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2C≡CCH3, and n is 0;
[0078] I.29: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The form is CH2CH2F, and n is 0;
[0079] I.30:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CHF2, and n is 0;
[0080] I.31: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CF3, and n is 0;
[0081] I.32: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2OCH3, and n is 0;
[0082] I.33:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2OCH2CH3, and n is 0;
[0083] I.35: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2SCH3, and n is 0;
[0084] I.37: R1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2SO2CH3, and n is 0;
[0085] I.40: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CN, and n is 0;
[0086] I.42: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The form is CH2COCH3, and n is 0;
[0087] I.70:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5O, and n is 0;
[0088] I.83:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 Let c = Pr, and n = 0;
[0089] I.84:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 Let c-Bn be the integer part of the integer part, and n be 0.
[0090] I.85: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is c-pentyl, and n is 0;
[0091] I.87: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is -CH2-c-Pr, and n is 0;
[0092] I.88:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is -CH2-c-Bn, where n is 0;
[0093] I.105: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5CH2, and n is 0;
[0094] I.109: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-Me-C6H4CH2, and n is 0;
[0095] I.110: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-F-C6H4CH2, and n is 0;
[0096] I.111: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-F-C6H4CH2, and n is 0;
[0097] I.112: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-F-C6H4CH2, and n is 0;
[0098] I.114: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2,4-di-F-C6H3CH2, and n is 0;
[0099] I.119: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R2 It is α-CH3-4-F-C6H4CH2, and n is 0;
[0100] I.122: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-NO2-C6H4CH2, and n is 0;
[0101] I.125: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-Cl-C6H4CH2, and n is 0;
[0102] I.126: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-CF3-C6H4CH2, and n is 0;
[0103] I.128: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CF3-C6H4CH2, and n is 0;
[0104] I.131: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCF3-C6H4CH2, and n is 0;
[0105] I.134: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CN-C6H4CH2, and n is 0;
[0106] I.138: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4CH2, and n is 0;
[0107] I.141: R1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-SCH3-C6H4CH2, and n is 0;
[0108] I.148: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 for n is 0;
[0109] I.153: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5-, and n is 0;
[0110] I.154: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-OCH3-C6H4-, and n is 0;
[0111] I.155: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-OCH3-C6H4-, and n is 0;
[0112] I.156: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4-, and n is 0;
[0113] I.157: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-CH3-C6H4-, and n is 0;
[0114] I.158: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2It is 3-CH3-C6H4-, and n is 0;
[0115] I.159: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CH3-C6H4-, and n is 0;
[0116] I.160: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-F-C6H4-, and n is 0;
[0117] I.161: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-F-C6H4-, and n is 0;
[0118] I.162: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-F-C6H4-, and n is 0;
[0119] I.172: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-NO2-C6H4-, and n is 0;
[0120] I.177: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is 4-CF3-C6H4-, and n is 0;
[0121] I.184: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-SCH3-C6H4-, and n is 0;
[0122] I.185: R 1 R 5 Both are CH3, R3 R 4 Both are H, R 2 It is 3-SCH3-C6H4-, and n is 0;
[0123] I.186: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-SCH3-C6H4-, and n is 0;
[0124] I.192: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is 4-SO2CH3-C6H4-, and n is 0;
[0125] I.201: R 1 R 2 R 5 Both are CH3, R 3 for R 4 H is a integer, and n is 0.
[0126] I.202:R 1 R 2 R 5 Both are CH3, R 3 for R 4 H is a integer, and n is 0.
[0127] I.203:R 1 R 2 R 3 R 4 R 5 All are CH3, n is 0;
[0128] I.286: R 1 R 3 R 4 Both are H, R 2 It is 4-MeO-C6H4, R 5 CH3, n is 0;
[0129] I.306:R 1 For Cl, R 2 It is 4-MeO-C6H4, R 3 R 4 Both are H, R 5 CH3, n is 0;
[0130] I.326: R 1 For NO2, R 2 It is 4-MeO-C6H4, R 3 R 4 Both are H, R 5 CH3, n is 0;
[0131] I.346: R 1 For CF3, R 2 It is 4-MeO-C6H4, R 3 R 4 Both are H, R 5 CH3, n is 0;
[0132] I.366:R 1 For OCH3, R 2 It is 4-MeO-C6H4, R 3 R 4 Both are H, R 5 CH3, n is 0;
[0133] I.386:R 1 For SO2CH3, R 2 It is 4-MeO-C6H4, R 3 R 4 Both are H, R 5 It is CH3, and n is 0.
[0134] According to the preferred embodiment 2, in formula (I), Q is the group represented by formula (Q2):
[0135] R 1 For H, C 1-12 alkyl, C 1-12 alkoxy, halogen, nitro, C substituted with at least one halogen 1-12 Alkyl or -S(O)2-R1; R1 is C 1-12 Alkyl groups;
[0136] R 2 C is H, unsubstituted, or substituted by at least one group in combination 2A. 1-12 alkyl, unsubstituted or substituted C groups of at least one of the groups in combination 2A 1-12 alkoxy, C 2-12 alkenyl, C 2-12 alkenyloxy group, unsubstituted or R2-substituted C 2-12 alkynyl, unsubstituted or R2-substituted C 2-12 alkynyloxy group, unsubstituted or derived from R 24 Substituted phenyl, unsubstituted or derived from R 24 Substituted phenyloxy, C 3-8Cycloalkyl groups or 3-8 membered unsaturated heterocycloalkyl groups containing at least one type A heteroatom; combination 2A contains halogen, C 1-12 alkoxy, C 1-12 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 -N(R) 22 (R) 23 ), cyano, -Si(R) 21 3、-C(O)-R 22 -COO-R 22 -CO-N(R) 22 (R) 23 C 3-8 cycloalkyl, unsubstituted or derived from R 25 Substituted 3-8 member saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom, unsubstituted or composed of at least one R 24 Substituted phenyl; R2 is selected from -Si(R 21 )3; 3 R 21 Each is independently selected from C 1-6 Alkyl group; R 24 Selected from halogens, C 1-6 alkyl, C 1-6 alkoxy, nitro, cyano, C groups substituted with at least one halogen 1-6 Alkyl groups, C substituted with at least one halogen 1-6 alkoxy, C 1-6 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 At least one of the following; Class A heteroatoms include N, O, and S; R 22 and R 23 Each is independently selected from H and C. 1-6 Any one of alkyl and benzyl groups; R 25 Selected from C 1-6 alkyl, C 3-8 cycloalkyl groups, C substituted with at least one halogen 1-6 At least one of the alkyl groups; R 3 Selected from H, C 1-6 Alkyl groups, C substituted with at least one halogen 1-6 Alkyl groups, C3 substituted with R3 1-6 R3 is selected from any one of alkyl or phenyl groups; R3 is selected from at least one of -S-R1, -SO-R1, -SO2-R1, and phenyl groups.
[0137] Or, R 2 and R 3 They can cyclize together to form saturated or unsaturated 5-7 membered rings;
[0138] R 4 Selected from H, C 1-6 Any one of the alkyl groups; R 5 Selected from H, C 1-12 Alkyl groups, C substituted with at least one halogen 1-12 Alkyl groups, C substituted with R5 1-6 alkyl, C 3-8 cycloalkyl, C 2-12 alkenyl, C 2-12 Any one of the alkynyl groups; R5 is -O-R1 or phenyl; n is 0, 1 or 2;
[0139] In equation (Q2), R 7 and R 8 Each is independently selected from H and C. 1-12 alkyl, C 3-8 cycloalkyl, phenyl-substituted C 7-12 Alkyl groups;
[0140] R 9 C selected from H, unsubstituted or substituted by at least one group from combination 9A 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl group, -C(R) 91 (R) 92 )-OC(O)-OR 93 -C(R) 91 (R) 92 )-OC(O)-SR 93 -C(R) 91 (R) 92 )-OC(O)-N(R 93 (R) 94 ), -C(R 91 (R) 92 )-C(O)-R 93 -C(O)-R 93 -COO-R 93 -C(O)-SR 93 -C(S)-OR 93 -C(O)-N(R) 93 (R) 94 -C(S)-N(R) 93 (R) 94 -S(O)2-R 93 -S(O)2-N(R) 93 (R) 94 -P(O)(OR) 93 (OR) 94Combination 9A contains halogens and C. 1-12 alkoxy, cyano, phenyl, or 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one class A heteroatom; R 91 and R 92 Each is independently selected from H and C. 1-6 Alkyl groups; or R 91 and R 92 Together they form 3-6 saturated rings; R 93 C selected from unsubstituted or substituted groups of at least one of the groups in combination 9A 1-12 alkyl, C 3-8 cycloalkyl, C 2-12 alkenyl, unsubstituted or derived from R 95 Substituted phenyl groups, 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom; R 94 Selected from H, C 1-6 Alkyl groups; or R 93 and R 94 Together they cyclize to form a 3-8 membered saturated or unsaturated heterocyclic group containing at least one type A heteroatom; R 95 Selected from halogens, C 1-6 alkyl, C 1-6 alkoxy groups.
[0141] In a preferred embodiment 2, more preferably, in formula (I), Q is a group represented by formula (Q2), and R in formula (Q2) 9 H is present; and the compound represented by formula (I) is selected from any one of the following:
[0142] II.1: R 1 R 5 R 7 R 8 Both are CH3, R 2 R 3 R 4 All are H, and n is 0;
[0143] II.2: R 1 R 2 R 7 R 8 Both are CH3, R 3 R 4 R 5 All are H, and n is 0;
[0144] II.3: R 1 R 2 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R5 CH3, n is 0;
[0145] II.10: R 1 R 2 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 5 For CH2CH=CH2, n is 0;
[0146] II.11: R 1 R 2 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 5 For CH2C≡CH, n is 0;
[0147] II.21: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CH3, and n is 0;
[0148] II.22: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH3, and n is 0;
[0149] II.23: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH2CH3, and n is 0;
[0150] II.24: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH2CH2CH3, and n is 0;
[0151] II.25: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH(CH3)CH2CH3, and n is 0;
[0152] II.26: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH(CH3)2, and n is 0;
[0153] II.27: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is C(CH3)3, and n is 0;
[0154] II.30: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH=CH2, n is 0;
[0155] II.31: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2C(CH3)=CH2, and n is 0;
[0156] II.33: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH=CH2, and n is 0;
[0157] II.34: R 1 R5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2C≡CH, n is 0;
[0158] II.35: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2C≡CCH3, and n is 0;
[0159] II.37: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The form is CH2CH2F, and n is 0;
[0160] II.38: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CHF2, and n is 0;
[0161] II.39: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CF3, and n is 0;
[0162] II.40: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2OCH3, and n is 0;
[0163] II.41: R 1 R 5 R 7 R 8 Both are CH3, R3 R 4 Both are H, R 2 The expression is CH2CH2OCH2CH3, and n is 0;
[0164] II.43: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2SCH3, and n is 0;
[0165] II.45: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2SO2CH3, and n is 0;
[0166] II.48: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CN, and n is 0;
[0167] II.78: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5O, and n is 0;
[0168] II.91: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 Let c = Pr, and n = 0;
[0169] II.92: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2Let c-Bn be the integer part of the integer part, and n be 0.
[0170] II.93: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is c-pentyl, and n is 0;
[0171] II.95: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is -CH2-c-Pr, and n is 0;
[0172] II.113: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5CH2, and n is 0;
[0173] II.117: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-Me-C6H4CH2, and n is 0;
[0174] II.118: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-F-C6H4CH2, and n is 0;
[0175] II.122: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2,4-di-F-C6H3CH2, and n is 0;
[0176] II.134: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-CF3-C6H4CH2, and n is 0;
[0177] II.135: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-CF3-C6H4CH2, and n is 0;
[0178] II.136: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CF3-C6H4CH2, and n is 0;
[0179] II.139: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCF3-C6H4CH2, and n is 0;
[0180] II.142: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CN-C6H4CH2, and n is 0;
[0181] II.146: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4CH2, and n is 0;
[0182] II.149: R1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-SCH3-C6H4CH2, and n is 0;
[0183] II.156: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 for n is 0;
[0184] II.161: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5-, and n is 0;
[0185] II.162: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-OCH3-C6H4-, and n is 0;
[0186] II.163: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-OCH3-C6H4-, and n is 0;
[0187] II.164: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4-, and n is 0;
[0188] II.165: R 1 R 5R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-CH3-C6H4-, and n is 0;
[0189] II.166: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-CH3-C6H4-, and n is 0;
[0190] II.167: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CH3-C6H4-, and n is 0;
[0191] II.168: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-F-C6H4-, and n is 0;
[0192] II.169: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-F-C6H4-, and n is 0;
[0193] II.170: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-F-C6H4-, and n is 0;
[0194] II.172: R 1 R 5 R 7 R 8Both are CH3, R 3 R 4 Both are H, R 2 The expression is 2,4-di-F-C6H3-, and n is 0;
[0195] II.177: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-Cl-C6H4-, and n is 0;
[0196] II.180: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-NO2-C6H4-, and n is 0;
[0197] II.185: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is 4-CF3-C6H4-, and n is 0;
[0198] II.191: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is 4-CN-C6H4-, and n is 0;
[0199] II.194: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-SCH3-C6H4-, and n is 0;
[0200] II.200: R 1 R 5 R 7 R 8 Both are CH3, R 3 R4 Both are H, R 2 The expression is 4-SO2CH3-C6H4-, and n is 0;
[0201] II.209: R 1 R 2 R 5 R 7 R 8 Both are CH3, R 3 for R 4 H is a integer, and n is 0.
[0202] II.210: R 1 R 2 R 5 R 7 R 8 Both are CH3, R 3 for R 4 H is a integer, and n is 0.
[0203] II.294: R 1 R 3 R 4 Both are H, R 5 R 7 R 8 Both are CH3, R 2 It is 4-MeO-C6H4, and n is 0;
[0204] II.314: R 1 For Cl, R 3 R 4 Both are H, R 5 R 7 R 8 Both are CH3, R 2 It is 4-MeO-C6H4, and n is 0;
[0205] II.334: R 1 For NO2, R 3 R 4 Both are H, R 5 R 7 R 8 Both are CH3, R 2 It is 4-MeO-C6H4, and n is 0;
[0206] II.374: R 1 For OCH3, R 3 R 4 Both are H, R 5 R 7 R 8Both are CH3, R 2 It is 4-MeO-C6H4, and n is 0;
[0207] II.394: R 1 For SO2CH3, R 3 R 4 Both are H, R 5 R 7 R 8 Both are CH3, R 2 It is 4-MeO-C6H4, and n is 0.
[0208] In a preferred embodiment 2, more preferably, in formula (I), Q is a group represented by formula (Q2); and the compound represented by formula (I) is selected from any one of the following:
[0209] III.4: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0210] III.5: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0211] III.7: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0212] III.8: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R9 for n is 0;
[0213] III.10: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0214] III.15: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0215] III.23: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0216] III.24: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0217] III.25: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0218] III.26: R1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0219] III.27: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0220] III.28: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0221] III.29: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0222] III.30: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0223] III.31: R 1 R 5 R 7 R 8 Both are CH3, R3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0224] III.32: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0225] III.33: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0226] III.34: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0227] III.35: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0228] III.36: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0229] III.37: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0230] III.38: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0231] III.39: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0232] III.40: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0233] III.43: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0234] III.44: R 1 R5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0235] III.45: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0236] III.48: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0237] III.51: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0238] III.52: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0239] III.54: R 1 R 5 R 7 R 8 Both are CH3, R 3 R4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0240] III.55: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0241] III.56: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0242] III.57: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0243] III.58: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0244] III.59: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0245] III.63: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0246] III.64: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0247] III.65: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0;
[0248] III.81: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0249] III.84: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0250] III.85: R 1 R 5R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0251] III.86: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0252] III.87: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0253] III.88: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0254] III.89: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0255] III.90: R 1 R 5 R 7 R 8 Both are CH3, R3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0256] III.91: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0257] III.95: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0258] III.101: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0259] III.105: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0260] III.112: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2It is 4-OCH3-C6H4, R 9 for n is 0;
[0261] III.119: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0262] III.120: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0263] III.121: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0;
[0264] III.129: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0.
[0265] This invention does not specifically limit the method for preparing compounds with the structure shown in formula (I). Those skilled in the art, having understood the compounds of this invention, can combine existing techniques in organic synthesis and known methods in the field to obtain suitable preparation routes to synthesize compounds with the structure shown in formula (I). To obtain higher product yields, several specific preparation methods for compounds with the structure shown in formula (I) are provided exemplarily below, and should not be construed as limiting the invention.
[0266] As previously stated, the second aspect of the present invention provides the application of the aforementioned benzo[a] polycyclic compound or its agriculturally chemically acceptable salt, hydrate, solvate, or its enantiomer or optically active derivative as an HPPD inhibitor in the control of weeds.
[0267] More preferably, the weeds are selected from at least one of broadleaf weeds, grass weeds and sedges.
[0268] The compounds provided by this invention have excellent herbicidal activity. Specifically, they can control at least one type of weed in peanut fields, soybean fields, cotton fields, wheat fields, rice fields, and corn fields. For example, they can control broadleaf weeds such as: shepherd's purse, shepherd's purse, lambsquarters, velvetleaf, cleavers, speedwell, chickweed, amaranth, black nightshade, purslane, purslane, amaranth purslane, and carp; grass weeds such as: barnyard grass, goosegrass, golden foxtail, foxtail grass, crabgrass, wild oat, Japanese wild oat, jointed goatgrass, wild oat, wild oat, bromegrass, and double-spike barnyard grass; and sedges such as: bulrush and sedge.
[0269] As mentioned above, a third aspect of the present invention provides an HPPD-inhibiting herbicide containing an effective amount of active ingredient for weed control. The active ingredient includes any one of the aforementioned benzo[a] polycyclic compound or its agriculturally chemically acceptable salt, hydrate, solvate, or its enantiomer or optically active derivative.
[0270] Preferably, the herbicide formulation is selected from at least one of wettable powder, soluble powder, emulsifiable concentrate, aqueous suspension, dispersible oil suspension, water emulsion, microemulsion, soluble liquid, or water-dispersible granules.
[0271] According to a preferred embodiment, the herbicide also contains a herbicide safener.
[0272] Preferably, the herbicide safener comprises at least one of 1,8-naphthalenedicarboxylic anhydride, dichloropropeneamine, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, furazolidone, cyclohexane, pyrazosulfuron, bis(oxazolyl) acid, cyclopropanesulfonamide, brassinolide, allyl oxychloride, and oxadiazon.
[0273] The pesticide herbicide of the present invention may also contain excipients.
[0274] 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.
[0275] 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.
[0276] 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.
[0277] 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.
[0278] 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.
[0279] 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.
[0280] 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.
[0281] 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.
[0282] 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.
[0283] 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.
[0284] Suitable bactericides used as excipients in this invention are bromonitrile glycol and isothiazolinone derivatives such as alkylisothiazolinone and benzisothiazolinone.
[0285] Suitable antifreeze agents used as excipients in this invention are ethylene glycol, propylene glycol, urea, and glycerin.
[0286] Suitable defoamers used as excipients in this invention are polysiloxanes, long-chain alcohols, and fatty acid salts.
[0287] 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).
[0288] Suitable thickeners or adhesives used as excipients in this invention are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biowax or synthetic wax, and cellulose ether.
[0289] In a preferred embodiment, the content of the active ingredient in the herbicide is 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%.
[0290] The benzo[a]polycyclic compounds provided by this invention have excellent crop safety.
[0291] 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.
[0292] 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.
[0293] 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.
[0294] 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.
[0295] Based on the compounds described in this invention, it is also possible to mix them with other insecticidal active substances such as insecticides, acaricides, herbicides and fungicides, as well as with safeners, fertilizers and / or plant growth regulators. The mixing method can be pre-mixed or bottled.
[0296] 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 benzo[a]polycyclic aromatic hydrocarbons: metolachlor, propargite, quinalazine, pyraclostrobin, flusulfanilamide, heptamethrin, chlorpyrifos, acetamiprid, pendimethalin, benzylsulfuron, diquat, clodinafop-methyl, atrazine, chlorsulfuron-methyl, metsulfuron-methyl, benzylsulfuron-methyl, thiamethoxam, pyrimimethoxam, formicin, methylsulfuron-methyl, nicosulfuron, acesulfuron-methyl, sulfadiazine ... 1,4-D cyprosulfuron, sulfadiazine, pyrimisulfuron, fluazolidone, trifluralin, flusulfanilamide, clethodim, ethoxysulfuron, glufosinate, bensulfuron, chlorfluazuron, ethyl ester, methyl methoxyfen, trifluralin, fluorinated oxyfen, propyzoxystrobin, bensulfuron-methyl, fluazinam, 2,4-D butyl ester, MCPA sodium, 2,4-D isooctyl ester, quizalofop-P-ethyl, quizalofop-P-ethyl, quizalofop-P-ethyl, quizalofop-P-ethyl , including quizalofop-P-ethyl, cyhalofop-butyl, oxazolidinone, clodinafop-propargyl, glyphosate, glufosinate, imazolidinone, imazolidinone ethionyl, imazolidinone quinclorac, methoxyfenozide, dichloropyridinic acid, ammonia-pyridinic acid, benzalkonium chloride, ethazinone, diflubenzuron, penoxsulam, sulfadiazine, chlorpyrifos, cyclopyridoxine, pyrimethanil, pyrimethanil, pyrimethanil, bispyribac-sodium, mesotrione, sulfadiazine, cyclopyridoxine, furazolidone, flupyrazole, cyclopyridoxine, cyclopyridoxine, cyclopyridoxine, cyclopyridoxine, cyclopyridoxine The following are some of the following: cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, pyrazosulfuron, furazolidone, oxadiazon, cyclopropanesulfonamide, bis(oxazolyl)acrylic acid, 1,8-naphthalenedicarboxylic anhydride, dichloropropeneamine, brassinolide, allyl oxychloride, oxadiazon, fluroxypyridine ester, chloropyridine ester, indolepyridine ester, fluroxypyridine, flusulfanilamide, trifluralin, fluproilamide, flupyrimisulfuron, flupyrimisulfuron, pyrimisulfuron, and cyclohexane.
[0297] When used, commercially available formulations should be 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 dosage of benzo[a]polycyclic aromatic hydrocarbons 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 between 0.005 and 500 g ai / ha, particularly between 0.005 and 250 g ai / ha.
[0298] 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.
[0299] 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.
[0300] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, all raw materials used are commercially available products.
[0301] Preparation Example 1: Preparation of Compound I.3
[0302] Preparation of intermediate AB: 15.1 g (0.10 mol) of 2-amino-6-methylbenzoic acid (AA) was placed in a 500 mL round-bottom flask. 100 mL of DMF solvent was added under stirring. The mixture was stirred at 0 °C. A solution of N-bromosuccinimide (19.6 g, 0.11 mol) dissolved in 100 mL of DMF was slowly added dropwise to the reaction system. Stirring was continued at 0 °C for approximately 2 h. The reaction was monitored by TLC. After the reaction was complete, the reaction solution was poured into 1 L of ice water under stirring. A white solid precipitated. The solid was collected by filtration, yielding 6-amino-3-bromo-2-methylbenzoic acid (AB), with a yield of 94%.
[0303] Preparation of intermediate ac: 21.5 g of intermediate ab was added to a 500 mL flask, followed by 250 mL of tetrahydrofuran and 22.3 g of triphosgene. The reaction was allowed to proceed overnight, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was poured into 1 L of ice water under stirring, and a white solid precipitated. The solid was collected by filtration, which was the product ac. Yield: 93%.
[0304] Preparation of intermediate AD: 22.0 g of intermediate AC was added to a 500 mL round-bottom flask, followed by 250 mL of DMF. 24.1 g of K₂CO₃ was then added with stirring, and the reaction was continued for approximately 30 min. Next, 18.6 g of iodomethane 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, 1 L of water was added to the system, resulting in the precipitation of a white solid. The solid was collected by filtration, yielding product AD, with a yield of 95%.
[0305] Preparation of intermediate ae: 22.0 g of intermediate ad was added to a 500 mL round-bottom flask, along with 250 mL of glacial acetic acid. 9.2 g of glycine was added with stirring, and the reaction was continued at 120 °C for approximately 6 h with stirring. After the reaction was complete, the glacial acetic acid was removed from the system by vacuum distillation. The remaining solid was added to water, stirred, and filtered. The collected solid was the product ae, with a yield of 90%.
[0306] Preparation of intermediate ae: 3.0 g of intermediate ae was added to a 100 mL round-bottom flask, along with 50 mL of DMF. While stirring, 3.0 g of K₂CO₃ was added, and the reaction was continued with stirring for approximately 30 min. Then, 2.3 g of iodomethane was slowly added dropwise to the reaction system. After the addition was complete, the reaction was stirred overnight at room temperature. After the reaction was complete, 400 mL of water was added to the system, and the reaction system was extracted three times with 150 mL of ethyl acetate each time. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain intermediate ae in 88% yield.
[0307] Preparation of intermediate ag: 2.8 g of intermediate af, 3.8 g of N,N'-dicyclohexylcarboimide, 104 mg of palladium acetate, and 269 mg of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene were added to a 250 mL two-necked flask. Nitrogen gas was introduced into the system, and 150 mL of DMF was added with stirring. Then, 2.5 mL of formic acid and 2.7 mL of triethylamine were added. The reaction was continued at 120 °C with stirring for approximately 12 h. After the reaction was complete, the mixture was filtered through a diatomaceous earth filter. 500 mL of water was added to the organic phase, and the reaction system was extracted three times with 150 mL of ethyl acetate each time. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain intermediate ag in 85% yield.
[0308] Preparation of intermediate ah: 2.4 g of intermediate ag was added to a 100 mL single-necked flask, followed by 50 mL of dry dichloromethane. 0.8 mL of oxaloyl chloride was slowly added dropwise at room temperature, followed by the catalytic amount of N,N-dimethylformamide. After the addition was complete, the mixture was stirred at room temperature for 3 h, and then the solvent was removed. 50 mL of dry dichloromethane, 1.5 g of cyclohexanedione, and 2.6 mL of triethylamine were added to the remaining solid, and the reaction was allowed to proceed for approximately 0.5 h. After the reaction was complete, the mixture was washed once with 25 mL of water, twice with 10 mL of saturated NaHCO3, dried over anhydrous Na2SO4, and column filtered to obtain intermediate ah in 65% yield.
[0309] Preparation of compound I.3: 2.1 g of intermediate ah was added to a 100 mL two-necked flask, followed by 40 mL of anhydrous acetonitrile. Under N2 protection, 1.7 mL of triethylamine and 25 mg of acetone cyanohydrin were added. The reaction was carried out at approximately 50 °C for 15 h, monitored by TLC 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 mixture was column-secreted, and the solvent was removed under reduced pressure to obtain the crude product. Recrystallization from diethyl ether yielded compound I.3 in 80% yield.
[0310] Preparation Example 2: Preparation of Compound I.83
[0311] Preparation of intermediate AI: At room temperature, 50.0 g of the compound represented by AA was added to a 1 L flask. 500 mL of glacial acetic acid was added with stirring. Then, 59.1 g of ICl was dissolved in 200 mL of glacial acetic acid and added dropwise to the reaction system over 30 min with stirring. After the addition was complete, the reaction mixture was stirred for approximately 3 h. After the reaction was complete, the reaction solution was filtered, and the resulting solid was washed with 400 mL of glacial acetic acid and dried to obtain intermediate AI, with a yield of 95%.
[0312] Preparation of intermediate aj: 87.1 g of intermediate ai was added to a 1 L flask, followed by 500 mL of tetrahydrofuran and 74.6 g of triphosgene. The reaction was allowed to proceed overnight, and the reaction was monitored by TLC. After the reaction was complete, the reaction solution was poured into 1 L of ice water under stirring, and a white solid precipitated. The solid was collected by filtration, which was the product aj. Yield: 93%.
[0313] Preparation of intermediate AK: 88.5 g of intermediate AJ was added to a 1 L round-bottom flask, along with 500 mL of DMF. While stirring, 80.8 g of K₂CO₃ was added, and the reaction was continued with stirring for approximately 30 min. Then, 62.2 g of iodomethane 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, 1 L of water was added to the system, and a white solid precipitated. The solid was collected by vacuum filtration, which yielded product AK, with a yield of 95%.
[0314] Preparation of intermediate AL: 3 g of intermediate AK was added to a 100 mL pear-shaped flask, followed by 50 mL of DMF, then 0.8 g of cyclopropylamine and 2.7 mL of triethylamine. The mixture was stirred at 80 °C for approximately 6 h. After the reaction was complete, the reaction mixture was poured into 200 mL of water, and the mixture was extracted three times with 100 mL of ethyl acetate each time. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain intermediate AL in 87% yield.
[0315] Preparation of intermediate am: The obtained intermediate al was added to a 100 mL pear-shaped flask and dissolved in 50 mL of dichloromethane. While stirring, 1.6 g of chloroacetyl chloride and 2.7 mL of triethylamine were added, and the mixture was stirred at room temperature for 1 h. After the reaction was complete, the solvent was removed by vacuum distillation to obtain the residue. The residue was dissolved in 50 mL of DMF, and then 6.1 g of cesium carbonate was added. The mixture was stirred at 80 °C for another 6 h. After the reaction was complete, the reaction mixture was poured into 200 mL of water, and the reaction mixture was extracted three times with 100 mL of ethyl acetate each time. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain intermediate am in 80% yield.
[0316] Preparation of intermediate an: Under nitrogen protection, 2.4 g of intermediate an, 245 mg of Pd(XantPhos)Cl2, 1.8 g of potassium carbonate, and 0.87 g of cyclohexanedione were added to a 250 mL two-necked flask. The mixture was dissolved in 100 mL of acetonitrile, and then 1.9 mL of triethylamine was added with stirring. The reaction was continued at 80 °C for 1 h with stirring. After the reaction was complete, the mixture was filtered through a diatomaceous earth filter, and the organic phase was collected and passed through a column chromatography column. The solvent was removed under reduced pressure to obtain intermediate an in 76% yield.
[0317] Preparation of compound I.83: 1.8 g of intermediate an was added to a 100 mL two-necked flask, followed by 40 mL of anhydrous acetonitrile. Under N2 protection, 1.5 mL of triethylamine and 25 mg of trimethylcyanosilane were added. The reaction was carried out at approximately 50 °C for 15 h, monitored by TLC 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 mixture was column-secreted, and the solvent was removed under reduced pressure to obtain the crude product. Recrystallization from diethyl ether yielded compound I.83, with a yield of 80%.
[0318] Preparation Example 3: Preparation of Compound I.105
[0319] Preparation of intermediate AO: 3.0 g of intermediate AE was added to a 100 mL round-bottom flask, followed by 50 mL of DMF. 3.0 g of K₂CO₃ was added with stirring, and the reaction was continued for approximately 30 min. Then, 2.7 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, 400 mL of water was added to the system, and the reaction mixture was extracted three times with 150 mL of ethyl acetate each time. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain intermediate AO in 90% yield.
[0320] Preparation of intermediate AP: 3.5 g of intermediate Ao, 3.9 g of N,N'-dicyclohexylcarboimide, 105 mg of palladium acetate, and 270 mg of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene were added to a 250 mL two-necked flask. Nitrogen gas was introduced into the system, and 150 mL of DMF was added with stirring. Then, 2.5 mL of formic acid and 2.7 mL of triethylamine were added. The reaction was continued at 120 °C with stirring for approximately 12 h. After the reaction was complete, the mixture was filtered through a diatomaceous earth filter. 500 mL of water was added to the organic phase, and the reaction system was extracted three times with 150 mL of ethyl acetate each time. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain intermediate AP in 85% yield.
[0321] Preparation of intermediate aq: 2.7 g of intermediate ap was added to a 100 mL single-necked flask, followed by 30 mL of dry THF. 1.4 g 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 dry dichloromethane, 1.07 g of cyclohexanedione, and 2.3 mL 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, dried over anhydrous Na2SO4, and column filtered to obtain intermediate aq in 73% yield.
[0322] Preparation of compound I.105: 2.5 g of intermediate aq was added to a 100 mL two-necked flask, followed by 40 mL of anhydrous acetonitrile. Under N2 protection, 1.7 mL of triethylamine and 28 mg of acetone cyanohydrin were added. The reaction was carried out at approximately 50 °C for 15 h, monitored by TLC 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 mixture was column-secreted, and the solvent was removed under reduced pressure to obtain the crude product. Recrystallization from diethyl ether yielded compound I.105, with a yield of 78%.
[0323] Preparation Example 4: Preparation of Compound I.156
[0324] Preparation of intermediate AR: 3g of intermediate AK was added to a 100mL pear-shaped flask, followed by 50mL of DMF, then 1.7g of p-methoxyaniline and 2.7mL of triethylamine. The mixture was stirred at 80℃ for approximately 6 hours. After the reaction was complete, the reaction mixture was poured into 200mL of water, and the mixture was extracted three times with 100mL of ethyl acetate each time. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain intermediate AR in 90% yield.
[0325] Preparation of intermediate as: The obtained intermediate ar was added to a 100 mL pear-shaped flask and dissolved in 50 mL of dichloromethane. 2.6 g of bromoacetyl bromide and 2.5 mL of triethylamine were added with stirring. The mixture was stirred at room temperature for 1 h. After the reaction was complete, the solvent was removed by vacuum distillation to obtain the residue. The residue was dissolved in 50 mL of DMF, and then 5.5 g of cesium carbonate was added. The mixture was stirred at 80 °C for another 6 h. After the reaction was complete, the reaction mixture was poured into 200 mL of water, and the reaction mixture was extracted three times with 100 mL of ethyl acetate each time. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain intermediate as, with a yield of 83%.
[0326] Preparation of intermediate AT: Under nitrogen protection, 3.1 g of intermediate AT, 268 mg of Pd(XantPhos)Cl2, 2.0 g of potassium carbonate, and 1.6 g of cyclohexanedione were added to a 250 mL two-necked flask. The mixture was dissolved in 100 mL of acetonitrile, and then 2.0 mL of triethylamine was added with stirring. The reaction was continued at 80 °C for 1 h with stirring. After the reaction was complete, the mixture was filtered through a diatomaceous earth filter, and the organic phase was collected and passed through a column. The solvent was removed under reduced pressure to obtain intermediate AT in 76% yield.
[0327] Preparation of compound I.156: 2.4 g of intermediate at was added to a 100 mL two-necked flask, followed by 50 mL of anhydrous acetonitrile. Under N2 protection, 1.5 mL of triethylamine and 25 mg of trimethylcyanosilane were added. The reaction was carried out at approximately 50 °C for 15 h, monitored by TLC 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 mixture was column-secreted, and the solvent was removed under reduced pressure to obtain the crude product. Recrystallization from diethyl ether yielded compound I.156, with a yield of 80%.
[0328] Preparation Example 5: Preparation of Compound II.3
[0329] Preparation of intermediate br: 2.4 g of intermediate ag was added to a 100 mL single-necked flask, followed by 50 mL of dry dichloromethane. 0.8 mL of oxaloyl chloride was slowly added dropwise at room temperature, followed by the catalytic amount of N,N-dimethylformamide. After the addition was complete, the mixture was stirred at room temperature for 3 h, and then the solvent was removed. 50 mL of dry dichloromethane, 1.5 g of 1,3-dimethyl-5-pyrazolone, and 2.6 mL of triethylamine were added to the remaining solid, and the reaction was allowed to proceed for approximately 0.5 h. After the reaction was complete, the mixture was washed once with 25 mL of water, twice with 10 mL of saturated NaHCO3, dried over anhydrous Na2SO4, and column filtered to obtain intermediate br in 62% yield.
[0330] Preparation of compound II.3: 2.1 g of intermediate br was added to a 100 mL two-necked flask, followed by 40 mL of anhydrous acetonitrile. Under N2 protection, 1.7 mL of triethylamine and 25 mg of acetone cyanohydrin were added. The reaction was carried out at approximately 50 °C for 15 h, monitored by TLC 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 obtain the crude product, which was then recrystallized from methanol to give compound II.3 in 61% yield.
[0331] Preparation Example 6: Preparation of Compound III.7
[0332] 300 mg of compound II.21 was added to a 50 mL flask, followed by 40 mL of anhydrous acetonitrile, then 528 mg of cesium carbonate and 204 mg of allyl iodine. The mixture was stirred at 60 °C for 3 h. After the reaction was complete, the solvent was removed under reduced pressure, and column chromatography was used to obtain the crude product. Recrystallization from diethyl ether gave a white solid III.7. Yield: 91%.
[0333] Preparation Example 7: Preparation of Compound III.28
[0334] 300 mg of compound II.21 was added to a 50 mL flask, followed by 25 mL of dry dichloromethane. 95 mg of acetyl chloride and 0.23 mL of triethylamine were slowly added dropwise at room temperature, followed by the addition of a catalytic amount of 4-dimethylaminopyridine. The mixture was stirred at room temperature for 3 h. After the reaction was complete, the mixture was washed once with 25 mL of water, then washed with 10 mL of saturated NaHCO3, dried over anhydrous Na2SO4, and purified by column chromatography under reduced pressure to obtain the crude product. Recrystallization from diethyl ether gave a white solid III.28. Yield: 86%.
[0335] The preparation methods of the other compounds of the present invention are the same as those described in the preparation examples above. Table 1 lists the characterization data of the compounds of the present invention.
[0336] Table 1
[0337] Note: "-" indicates an oily substance.
[0338] Test Example 1
[0339] This test example illustrates the herbicidal activity (expressed as growth inhibition rate (%)) of compounds with the structure shown in formula (I) and comparative compounds.
[0340] Herbicidal activity test (pot method): The test targets were barnyard grass, foxtail grass, crabgrass, amaranth, lamb's quarters, and velvetleaf. Post-emergence foliar spraying: 7cm inner diameter paper cups were filled with composite soil (garden soil: seedling substrate, 1:2, v / v) to 3 / 4 full, and weeds were directly sown, covered with 0.2cm of soil, and left to grow to the 4-5 leaf stage. The compounds of this invention and the aforementioned comparative compounds were applied at a dosage of 150g ai / ha (grams per hectare) using an automatic spray tower. After the foliar spray dried, the crops were transferred to a greenhouse for cultivation (25℃, 70% humidity), and the results were investigated after 30 days. The growth inhibition rate was evaluated visually, specifically according to the conditions shown in Table 2. The inhibition rate (%) results are shown in Table 3.
[0341] Table 2
[0342] Table 3
[0343] "-" indicates that it has not been tested.
[0344] In herbicidal activity tests, the compounds reported in this invention exhibited excellent herbicidal activity against six common grasses and broadleaf weeds: barnyard grass, foxtail, crabgrass, amaranth, lambsquarters, and velvetleaf. Most of the compounds in this invention showed 100% herbicidal efficacy against the six tested weeds at an application rate of 150 g ai / ha. Therefore, the compounds in this invention have strong development and commercialization potential.
[0345] Test Example 2
[0346] The herbicidal activity of the compound of the present invention in reducing weed dosage was tested using the same test and evaluation methods as in Test Example 1. The test results are shown in Table 4.
[0347] Table 4
[0348] "-" indicates that it has not been tested.
[0349] The results shown above demonstrate that the representative compounds of this invention exhibit excellent herbicidal activity against barnyard grass, foxtail grass, crabgrass, wild oats, wild oats, ryegrass, amaranth, and velvetleaf at reduced dosages, such as 30 g ai / ha, 60 g ai / ha, and 120 g ai / ha. Most compounds completely inhibited weed growth. Therefore, the compounds of this invention have strong prospects for development and commercialization.
[0350] Test Example 3
[0351] The crop safety of the compounds of the present invention was determined using the same test and evaluation methods as in Test Example 1. The test results are shown in Tables 5, 6 and 7.
[0352] Table 5
[0353] Table 6
[0354] Table 7
[0355] The results shown above demonstrate that, at doses of 120, 60, and 30 g ai / ha, compounds I.1 and I.42 exhibited excellent crop safety in maize, while compounds I.126, I.156, II.134, and II.164 exhibited excellent crop safety in wheat. Compounds I.1, I.126, II.21, II.30, II.134, and II.164 all exhibited excellent crop safety in peanuts.
[0356] As the foregoing results show, the benzo[a]polycyclic 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 aequalis*, *Oryza sativa*, *Brassica rapa*, *Echinochloa crus-galli*, and *Paspalum distichum*. Sedges include: *Iris tectorum* and *Cyperus difformis*. Furthermore, the compounds of this invention exhibit high safety for crops.
[0357] 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 benzo[a] polycyclic compound or its agrochemically acceptable salt, hydrate, solvate, or its enantiomer or optically active derivative, characterized in that, The compound has the structure shown in formula (I): In equation (I), Q is a group represented by formula (Q1) or formula (Q2); R 1 For H, C 1-30 alkyl, C 1-30 alkoxy, halogen, nitro, C substituted with at least one halogen 1-24 Alkyl or -S(O)2-R1; R1 is C 1-24 Alkyl groups; R 2 C is H, unsubstituted, or substituted by at least one group in combination 2A. 1-30 alkyl, unsubstituted or substituted C groups of at least one of the groups in combination 2A 1-30 alkoxy, C 2-24 alkenyl, C 2-24 alkenyloxy group, unsubstituted or R2-substituted C 2-24 alkynyl, unsubstituted or R2-substituted C 2-24 alkynyloxy group, unsubstituted or derived from R 24 Substituted phenyl, unsubstituted or derived from R 24 Substituted phenyloxy, C 3-8 Cycloalkyl groups or 3-8 membered unsaturated heterocycloalkyl groups containing at least one type A heteroatom; combination 2A contains halogen, C 1-24 alkoxy, C 1-24 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 -N(R) 22 (R) 23 ), cyano, -Si(R) 21 3、-C(O)-R 22 -COO-R 22 -CO-N(R) 22 (R) 23 C 3-8 cycloalkyl, unsubstituted or derived from R 25 Substituted 3-8 member saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom, unsubstituted or composed of at least one R 24 Substituted phenyl; R2 is selected from -Si(R 21 )3; 3 R 21 Each is independently selected from C 1-12 Alkyl group; R 24 Selected from halogens, C 1-24 alkyl, C 1-24 alkoxy, nitro, cyano, C groups substituted with at least one halogen 1-24 Alkyl groups, C substituted with at least one halogen 1-24 alkoxy, C 1-24 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 At least one of the following; Class A heteroatoms include N, O, and S; R 22 and R 23 Each is independently selected from H and C. 1-24 Any one of alkyl and benzyl groups; R 25 Selected from C 3-8 cycloalkyl, unsubstituted or C substituted with at least one halogen 1-12 At least one of the alkyl groups; R 3 Selected from H, C 1-24 Alkyl groups, C substituted with at least one halogen 1-24 Alkyl groups, C3 substituted with R3 1-24 R3 is selected from any one of alkyl or phenyl groups; R3 is selected from at least one of -S-R1, -SO-R1, -SO2-R1, and phenyl groups. Or, R 2 and R 3 They can cyclize together to form saturated or unsaturated 5-7 membered rings; R 4 Selected from H, C 1-24 Any one of the alkyl groups; R 5 Selected from H, C 1-24 Alkyl groups, C substituted with at least one halogen 1-24 Alkyl groups, C substituted with R5 1-24 alkyl, C 3-8 cycloalkyl, C 2-24 alkenyl, C 2-24 Any one of the alkynyl groups; R5 is -O-R1 or phenyl; n is 0, 1, or 2; In equation (Q1), x R 6 Each is independently selected from H and C. 1-12 Alkyl groups, where x is an integer from 1 to 6; In equation (Q2), R 7 and R 8 Each is independently selected from H and C. 1-24 alkyl, C 3-8 Cycloalkyl, phenyl-substituted C 7-24 Alkyl groups; R 9 C selected from H, unsubstituted or substituted by at least one group from combination 9A 1-24 alkyl, C 2-24 alkenyl, C 2-24 alkynyl group, -C(R) 91 (R) 92 )-OC(O)-OR 93 -C(R) 91 (R) 92 )-OC(O)-SR 93 -C(R) 91 (R) 92 )-OC(O)-N(R 93 (R) 94 ), -C(R 91 (R) 92 )-C(O)-R 93 -C(O)-R 93 -COO-R 93 -C(O)-SR 93 -C(S)-OR 93 -C(O)-N(R) 93 (R) 94 -C(S)-N(R) 93 (R) 94 -S(O)2-R 93 -S(O)2-N(R) 93 (R) 94 -P(O)(OR) 93 (OR) 94 Combination 9A contains halogens and C. 1-24 alkoxy, cyano, phenyl, or 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one class A heteroatom; R 91 and R 92 Each is independently selected from H and C. 1-24 Alkyl groups; or R 91 and R 92 Together they form 3-6 saturated rings; R 93 C selected from unsubstituted or substituted groups of at least one of the groups in combination 9A 1-24 alkyl, C 3-8 cycloalkyl, C 2-24 alkenyl, unsubstituted or derived from R 95 Substituted phenyl groups, 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom; R 94 Selected from H, C 1-12 Alkyl groups; or R 93 and R 94 Together they cyclize to form a 3-8 membered saturated or unsaturated heterocyclic group containing at least one type A heteroatom; R 95 Selected from halogens, C 1-12 alkyl, C 1-12 alkoxy groups.
2. The compound according to claim 1, characterized in that, In formula (I), Q is the group represented by formula (Q1) or formula (Q2): R 1 For H, C 1-12 alkyl, C 1-12 alkoxy, halogen, nitro, C substituted with at least one halogen 1-12 Alkyl or -S(O)2-R1; R1 is C 1-12 Alkyl groups; R 2 C is H, unsubstituted, or substituted by at least one group in combination 2A. 1-12 alkyl, unsubstituted or substituted C groups of at least one of the groups in combination 2A 1-12 alkoxy, C 2-12 alkenyl, C 2-12 alkenyloxy group, unsubstituted or R2-substituted C 2-12 alkynyl, unsubstituted or R2-substituted C 2-12 alkynyloxy group, unsubstituted or derived from R 24 Substituted phenyl, unsubstituted or derived from R 24 Substituted phenyloxy, C 3-8 Cycloalkyl groups or 3-8 membered unsaturated heterocycloalkyl groups containing at least one type A heteroatom; combination 2A contains halogen, C 1-12 alkoxy, C 1-12 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 -N(R) 22 (R) 23 ), cyano, -Si(R) 21 3、-C(O)-R 22 -COO-R 22 -CO-N(R) 22 (R) 23 C 3-8 cycloalkyl, unsubstituted or derived from R 25 Substituted 3-8 member saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom, unsubstituted or composed of at least one R 24 Substituted phenyl; R2 is selected from -Si(R 21 )3; 3 R 21 Each is independently selected from C 1-6 Alkyl group; R 24 Selected from halogens, C 1-6 alkyl, C 1-6 alkoxy, nitro, cyano, C groups substituted with at least one halogen 1-6 Alkyl groups, C substituted with at least one halogen 1-6 alkoxy, C 1-6 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 At least one of the following; Class A heteroatoms include N, O, and S; R 22 and R 23 Each is independently selected from H and C. 1-6 Any one of alkyl and benzyl groups; R 25 Selected from C 1-6 alkyl, C 3-8 cycloalkyl groups, C substituted with at least one halogen 1-6 At least one of the alkyl groups; R 3 Selected from H, C 1-6 Alkyl groups, C substituted with at least one halogen 1-6 Alkyl groups, C3 substituted with R3 1-6 R3 is selected from any one of alkyl or phenyl groups; R3 is selected from at least one of -S-R1, -SO-R1, -SO2-R1, and phenyl groups. Or, R 2 and R 3 They can cyclize together to form saturated or unsaturated 5-7 membered rings; R 4 Selected from H, C 1-6 Any one of the alkyl groups; R 5 Selected from H, C 1-12 Alkyl groups, C substituted with at least one halogen 1-12 Alkyl groups, C substituted with R5 1-6 alkyl, C 3-8 cycloalkyl, C 2-12 alkenyl, C 2-12 Any one of the alkynyl groups; R5 is -O-R1 or phenyl; n is 0, 1, or 2; In equation (Q1), x R 6 Each is independently selected from H and C. 1-6 Alkyl groups, where x is an integer from 1 to 6; In equation (Q2), R 7 and R 8 Each is independently selected from H and C. 1-12 alkyl, C 3-8 Cycloalkyl, phenyl-substituted C 7-12 Alkyl groups; R 9 C selected from H, unsubstituted or substituted by at least one group from combination 9A 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl group, -C(R) 91 (R) 92 )-OC(O)-OR 93 -C(R) 91 (R) 92 )-OC(O)-SR 93 -C(R) 91 (R) 92 )-OC(O)-N(R 93 (R) 94 ), -C(R 91 (R) 92 )-C(O)-R 93 -C(O)-R 93 -COO-R 93 -C(O)-SR 93 -C(S)-OR 93 -C(O)-N(R) 93 (R) 94 -C(S)-N(R) 93 (R) 94 -S(O)2-R 93 -S(O)2-N(R) 93 (R) 94 -P(O)(OR) 93 (OR) 94 Combination 9A contains halogens and C. 1-12 alkoxy, cyano, phenyl, or 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one class A heteroatom; R 91 and R 92 Each is independently selected from H and C. 1-6 Alkyl groups; or R 91 and R 92 Together they form 3-6 saturated rings; R 93 C selected from unsubstituted or substituted groups of at least one of the groups in combination 9A 1-12 alkyl, C 3-8 cycloalkyl, C 2-12 alkenyl, unsubstituted or derived from R 95 Substituted phenyl groups, 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom; R 94 Selected from H, C 1-6 Alkyl groups; or R 93 and R 94 Together they cyclize to form a 3-8 membered saturated or unsaturated heterocyclic group containing at least one type A heteroatom; R 95 Selected from halogens, C 1-6 alkyl, C 1-6 alkoxy groups.
3. The compound according to claim 2, characterized in that, In formula (I), Q is the group represented by formula (Q1): R 1 For H, C 1-12 alkyl, C 1-12 alkoxy, halogen, nitro, C substituted with at least one halogen 1-12 Alkyl or -S(O)2-R1; R1 is C 1-12 Alkyl groups; R 2 C is H, unsubstituted, or substituted by at least one group in combination 2A. 1-12 alkyl, unsubstituted or substituted C groups of at least one of the groups in combination 2A 1-12 alkoxy, C 2-12 alkenyl, C 2-12 alkenyloxy group, unsubstituted or R2-substituted C 2-12 alkynyl, unsubstituted or R2-substituted C 2-12 alkynyloxy group, unsubstituted or derived from R 24 Substituted phenyl, unsubstituted or derived from R 24 Substituted phenyloxy, C 3-8 Cycloalkyl groups or 3-8 membered unsaturated heterocycloalkyl groups containing at least one type A heteroatom; combination 2A contains halogen, C 1-12 alkoxy, C 1-12 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 -N(R) 22 (R) 23 ), cyano, -Si(R) 21 3、-C(O)-R 22 -COO-R 22 -CO-N(R) 22 (R) 23 C 3-8 cycloalkyl, unsubstituted or derived from R 25 Substituted 3-8 member saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom, unsubstituted or composed of at least one R 24 Substituted phenyl; R2 is selected from -Si(R 21 )3; 3 R 21 Each is independently selected from C 1-6 Alkyl group; R 24 Selected from halogens, C 1-6 alkyl, C 1-6 alkoxy, nitro, cyano, C groups substituted with at least one halogen 1-6 Alkyl groups, C substituted with at least one halogen 1-6 alkoxy, C 1-6 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 At least one of the following; Class A heteroatoms include N, O, and S; R 22 and R 23 Each is independently selected from H and C. 1-6 Any one of alkyl and benzyl groups; R 25 Selected from C 1-6 alkyl, C 3-8 cycloalkyl groups, C substituted with at least one halogen 1-6 At least one of the alkyl groups; R 3 Selected from H, C 1-6 Alkyl groups, C substituted with at least one halogen 1-6 Alkyl groups, C3 substituted with R3 1-6 R3 is selected from any one of alkyl or phenyl groups; R3 is selected from at least one of -S-R1, -SO-R1, -SO2-R1, and phenyl groups. Or, R 2 and R 3 They can cyclize together to form saturated or unsaturated 5-7 membered rings; R 4 Selected from H, C 1-3 Any one of the alkyl groups; R 5 Selected from H, C 1-12 Alkyl groups, C substituted with at least one halogen 1-12 Alkyl groups, C substituted with R5 1-6 alkyl, C 3-8 cycloalkyl, C 2-12 alkenyl, C 2-12 Any one of the alkynyl groups; R5 is -O-R1 or phenyl; n is 0, 1, or 2.
4. The compound according to claim 3, characterized in that, In formula (I), Q is the group represented by formula (Q1), and R in formula (Q1) 6 All are H; and the compound represented by formula (I) is selected from any one of the following: I.1: R 1 R 5 Both are CH3, R 2 R 3 R 4 All are H, and n is 0; I.2: R 1 R 2 Both are CH3, R 3 R 4 R 5 All are H, and n is 0; I.3: R 1 R 2 R 5 Both are CH3, R 3 R 4 All are H, and n is 0; I.8:R 1 R 2 Both are CH3, R 3 R 4 Both are H, R 5 The form is CH2CH2F, and n is 0; I.10: R 1 R 2 Both are CH3, R 3 R 4 Both are H, R 5 The expression is CH2CH=CH2, and n is 0; I.11: R 1 R 2 Both are CH3, R 3 R 4 Both are H, R 5 The expression is CH2C≡CH, and n is 0; I.13: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CH3, and n is 0; I.14: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH3, and n is 0; I.15: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH2CH3, and n is 0; I.16: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH2CH2CH3, and n is 0; I.17: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH(CH3)CH2CH3, and n is 0; I.18: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH(CH3)2, and n is 0; I.19: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is C(CH3)3, and n is 0; I.22: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH=CH2, and n is 0; I.23: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2C(CH3)=CH2, and n is 0; I.25: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH=CH2, and n is 0; I.26: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2C≡CH, and n is 0; I.27: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2C≡CCH3, and n is 0; I.29: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The form is CH2CH2F, and n is 0; I.30:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CHF2, and n is 0; I.31: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CF3, and n is 0; I.32: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2OCH3, and n is 0; I.33:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2OCH2CH3, and n is 0; I.35: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2SCH3, and n is 0; I.37: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The form is CH2CH2SO2CH3, and n is 0; I.40: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CN, and n is 0; I.42: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The form is CH2COCH3, and n is 0; I.70:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5O, and n is 0; I.83:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 Let c = Pr, and n = 0; I.84:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 Let c-Bn be the integer part of the integer part, and n be 0. I.85: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is c-pentyl, and n is 0; I.87: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is -CH2-c-Pr, and n is 0; I.88:R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is -CH2-c-Bn, where n is 0; I.105: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5CH2, and n is 0; I.109: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-Me-C6H4CH2, and n is 0; I.110: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-F-C6H4CH2, and n is 0; I.111: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-F-C6H4CH2, and n is 0; I.112: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-F-C6H4CH2, and n is 0; I.114: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2,4-di-F-C6H3CH2, and n is 0; I.119: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is α-CH3-4-F-C6H4CH2, and n is 0; I.122: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-NO2-C6H4CH2, and n is 0; I.125: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-Cl-C6H4CH2, and n is 0; I.126: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-CF3-C6H4CH2, and n is 0; I.128: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CF3-C6H4CH2, and n is 0; I.131: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCF3-C6H4CH2, and n is 0; I.134: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CN-C6H4CH2, and n is 0; I.138: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4CH2, and n is 0; I.141: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-SCH3-C6H4CH2, and n is 0; I.148: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 for n is 0; I.153: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5-, and n is 0; I.154: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-OCH3-C6H4-, and n is 0; I.155: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-OCH3-C6H4-, and n is 0; I.156: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4-, and n is 0; I.157: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-CH3-C6H4-, and n is 0; I.158: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-CH3-C6H4-, and n is 0; I.159: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CH3-C6H4-, and n is 0; I.160: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-F-C6H4-, and n is 0; I.161: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-F-C6H4-, and n is 0; I.162: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-F-C6H4-, and n is 0; I.172: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-NO2-C6H4-, and n is 0; I.177: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is 4-CF3-C6H4-, and n is 0; I.184: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-SCH3-C6H4-, and n is 0; I.185: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-SCH3-C6H4-, and n is 0; I.186: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-SCH3-C6H4-, and n is 0; I.192: R 1 R 5 Both are CH3, R 3 R 4 Both are H, R 2 The expression is 4-SO2CH3-C6H4-, and n is 0; I.201: R 1 R 2 R 5 Both are CH3, R 3 for R 4 H is a integer, and n is 0. I.202:R 1 R 2 R 5 Both are CH3, R 3 for R 4 H is a integer, and n is 0. I.203:R 1 R 2 R 3 R 4 R 5 All are CH3, n is 0; I.286: R 1 R 3 R 4 Both are H, R 2 It is 4-MeO-C6H4, R 5 CH3, n is 0; I.306:R 1 For Cl, R 2 It is 4-MeO-C6H4, R 3 R 4 Both are H, R 5 CH3, n is 0; I.326: R 1 For NO2, R 2 It is 4-MeO-C6H4, R 3 R 4 Both are H, R 5 CH3, n is 0; I.346: R 1 For CF3, R 2 It is 4-MeO-C6H4, R 3 R 4 Both are H, R 5 CH3, n is 0; I.366:R 1 For OCH3, R 2 It is 4-MeO-C6H4, R 3 R 4 Both are H, R 5 CH3, n is 0; I.386: R 1 For SO2CH3, R 2 It is 4-MeO-C6H4, R 3 R 4 Both are H, R 5 It is CH3, and n is 0.
5. The compound according to claim 2, characterized in that, In formula (I), Q is the group represented by formula (Q2): R 1 For H, C 1-12 alkyl, C 1-12 alkoxy, halogen, nitro, C substituted with at least one halogen 1-12 Alkyl or -S(O)2-R1; R1 is C 1-12 Alkyl groups; R 2 C is H, unsubstituted, or substituted by at least one group in combination 2A. 1-12 alkyl, unsubstituted or substituted C groups of at least one of the groups in combination 2A 1-12 alkoxy, C 2-12 alkenyl, C 2-12 alkenyloxy group, unsubstituted or R2-substituted C 2-12 alkynyl, unsubstituted or R2-substituted C 2-12 alkynyloxy group, unsubstituted or derived from R 24 Substituted phenyl, unsubstituted or derived from R 24 Substituted phenyloxy, C 3-8 Cycloalkyl groups or 3-8 membered unsaturated heterocycloalkyl groups containing at least one type A heteroatom; combination 2A contains halogen, C 1-12 alkoxy, C 1-12 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 -N(R) 22 (R) 23 ), cyano, -Si(R) 21 3、-C(O)-R 22 -COO-R 22 -CO-N(R) 22 (R) 23 C 3-8 cycloalkyl, unsubstituted or derived from R 25 Substituted 3-8 member saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom, unsubstituted or composed of at least one R 24 Substituted phenyl; R2 is selected from -Si(R 21 )3; 3 R 21 Each is independently selected from C 1-6 Alkyl group; R 24 Selected from halogens, C 1-6 alkyl, C 1-6 alkoxy, nitro, cyano, C groups substituted with at least one halogen 1-6 Alkyl groups, C substituted with at least one halogen 1-6 alkoxy, C 1-6 alkylthio groups, -S(O)-R 22 -S(O)2-R 22 At least one of the following; Class A heteroatoms include N, O, and S; R 22 and R 23 Each is independently selected from H and C. 1-6 Any one of alkyl and benzyl groups; R 25 Selected from C 1-6 alkyl, C 3-8 cycloalkyl groups, C substituted with at least one halogen 1-6 At least one of the alkyl groups; R 3 Selected from H, C 1-6 Alkyl groups, C substituted with at least one halogen 1-6 Alkyl groups, C3 substituted with R3 1-6 R3 is selected from any one of alkyl or phenyl groups; R3 is selected from at least one of -S-R1, -SO-R1, -SO2-R1, and phenyl groups. Or, R 2 and R 3 They can cyclize together to form saturated or unsaturated 5-7 membered rings; R 4 Selected from H, C 1-6 Any one of the alkyl groups; R 5 Selected from H, C 1-12 Alkyl groups, C substituted with at least one halogen 1-12 Alkyl groups, C substituted with R5 1-6 alkyl, C 3-8 cycloalkyl, C 2-12 alkenyl, C 2-12 Any one of the alkynyl groups; R5 is -O-R1 or phenyl; n is 0, 1, or 2; In equation (Q2), R 7 and R 8 Each is independently selected from H and C. 1-12 alkyl, C 3-8 Cycloalkyl, phenyl-substituted C 7-12 Alkyl groups; R 9 C selected from H, unsubstituted or substituted by at least one group from combination 9A 1-12 alkyl, C 2-12 alkenyl, C 2-12 alkynyl group, -C(R) 91 (R) 92 )-OC(O)-OR 93 -C(R) 91 (R) 92 )-OC(O)-SR 93 -C(R) 91 (R) 92 )-OC(O)-N(R 93 (R) 94 ), -C(R 91 (R) 92 )-C(O)-R 93 -C(O)-R 93 -COO-R 93 -C(O)-SR 93 -C(S)-OR 93 -C(O)-N(R) 93 (R) 94 -C(S)-N(R) 93 (R) 94 -S(O)2-R 93 -S(O)2-N(R) 93 (R) 94 -P(O)(OR) 93 (OR) 94 Combination 9A contains halogens and C. 1-12 alkoxy, cyano, phenyl, or 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one class A heteroatom; R 91 and R 92 Each is independently selected from H and C. 1-6 Alkyl groups; or R 91 and R 92 Together they form 3-6 saturated rings; R 93 C selected from unsubstituted or substituted groups of at least one of the groups in combination 9A 1-12 alkyl, C 3-8 cycloalkyl, C 2-12 alkenyl, unsubstituted or derived from R 95 Substituted phenyl groups, 3-8 membered saturated or unsaturated heterocyclic alkyl groups containing at least one type A heteroatom; R 94 Selected from H, C 1-6 Alkyl groups; or R 93 and R 94 Together they cyclize to form a 3-8 membered saturated or unsaturated heterocyclic group containing at least one type A heteroatom; R 95 Selected from halogens, C 1-6 alkyl, C 1-6 alkoxy groups.
6. The compound according to claim 5, characterized in that, In formula (I), Q is the group represented by formula (Q2), and R in formula (Q2) 9 H is present; and the compound represented by formula (I) is selected from any one of the following: II.1: R 1 R 5 R 7 R 8 Both are CH3, R 2 R 3 R 4 All are H, and n is 0; II.2: R 1 R 2 R 7 R 8 Both are CH3, R 3 R 4 R 5 All are H, and n is 0; II.3: R 1 R 2 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 5 CH3, n is 0; II.10: R 1 R 2 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 5 The expression is CH2CH=CH2, and n is 0; II.11: R 1 R 2 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 5 The expression is CH2C≡CH, and n is 0; II.21: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CH3, and n is 0; II.22: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH3, and n is 0; II.23: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH2CH3, and n is 0; II.24: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH2CH2CH3, and n is 0; II.25: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH(CH3)CH2CH3, and n is 0; II.26: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH(CH3)2, and n is 0; II.27: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is C(CH3)3, and n is 0; II.30: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH=CH2, and n is 0; II.31: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2C(CH3)=CH2, and n is 0; II.33: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CH=CH2, and n is 0; II.34: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2C≡CH, and n is 0; II.35: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2C≡CCH3, and n is 0; II.37: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The form is CH2CH2F, and n is 0; II.38: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CHF2, and n is 0; II.39: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is CH2CF3, and n is 0; II.40: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2OCH3, and n is 0; II.41: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2OCH2CH3, and n is 0; II.43: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2SCH3, and n is 0; II.45: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The form is CH2CH2SO2CH3, and n is 0; II.48: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is CH2CH2CN, and n is 0; II.78: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5O, and n is 0; II.91: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 Let c = Pr, and n = 0; II.92: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 Let c-Bn be the integer part of the integer part, and n be 0. II.93: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is c-pentyl, and n is 0; II.95: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is -CH2-c-Pr, and n is 0; II.113: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5CH2, and n is 0; II.117: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-Me-C6H4CH2, and n is 0; II.118: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-F-C6H4CH2, and n is 0; II.122: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2,4-di-F-C6H3CH2, and n is 0; II.134: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-CF3-C6H4CH2, and n is 0; II.135: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-CF3-C6H4CH2, and n is 0; II.136: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CF3-C6H4CH2, and n is 0; II.139: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCF3-C6H4CH2, and n is 0; II.142: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CN-C6H4CH2, and n is 0; II.146: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4CH2, and n is 0; II.149: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-SCH3-C6H4CH2, and n is 0; II.156: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 for n is 0; II.161: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is C6H5-, and n is 0; II.162: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-OCH3-C6H4-, and n is 0; II.163: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-OCH3-C6H4-, and n is 0; II.164: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4-, and n is 0; II.165: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-CH3-C6H4-, and n is 0; II.166: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-CH3-C6H4-, and n is 0; II.167: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-CH3-C6H4-, and n is 0; II.168: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-F-C6H4-, and n is 0; II.169: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 3-F-C6H4-, and n is 0; II.170: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-F-C6H4-, and n is 0; II.172: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is 2,4-di-F-C6H3-, and n is 0; II.177: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-Cl-C6H4-, and n is 0; II.180: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 2-NO2-C6H4-, and n is 0; II.185: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is 4-CF3-C6H4-, and n is 0; II.191: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is 4-CN-C6H4-, and n is 0; II.194: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-SCH3-C6H4-, and n is 0; II.200: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 The expression is 4-SO2CH3-C6H4-, and n is 0; II.209: R 1 R 2 R 5 R 7 R 8 Both are CH3, R 3 for R 4 H is a integer, and n is 0. II.210: R 1 R 2 R 5 R 7 R 8 Both are CH3, R 3 for R 4 H is a integer, and n is 0. II.294: R 1 R 3 R 4 Both are H, R 5 R 7 R 8 Both are CH3, R 2 It is 4-MeO-C6H4, and n is 0; II.314: R 1 For Cl, R 3 R 4 Both are H, R 5 R 7 R 8 Both are CH3, R 2 It is 4-MeO-C6H4, and n is 0; II.334: R 1 For NO2, R 3 R 4 Both are H, R 5 R 7 R 8 Both are CH3, R 2 It is 4-MeO-C6H4, and n is 0; II.374: R 1 For OCH3, R 3 R 4 Both are H, R 5 R 7 R 8 Both are CH3, R 2 It is 4-MeO-C6H4, and n is 0; II.394: R 1 For SO2CH3, R 3 R 4 Both are H, R 5 R 7 R 8 Both are CH3, R 2 It is 4-MeO-C6H4, and n is 0.
7. The compound according to claim 5, characterized in that, In formula (I), Q is the group represented by formula (Q2); and the compound represented by formula (I) is selected from any one of the following: III.4: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.5: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.7: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.8: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.10: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.15: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.23: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.24: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.25: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.26: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.27: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.28: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.29: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.30: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.31: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.32: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.33: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.34: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.35: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.36: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.37: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.38: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.39: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.40: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.43: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.44: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.45: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.48: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.51: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.52: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.54: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.55: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.56: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.57: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.58: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.59: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.63: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.64: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.65: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 For CH2CH3, R 9 for n is 0; III.81: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.84: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.85: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.86: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.87: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.88: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.89: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.90: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.91: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.95: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.101: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.105: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.112: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.119: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.120: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.121: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0; III.129: R 1 R 5 R 7 R 8 Both are CH3, R 3 R 4 Both are H, R 2 It is 4-OCH3-C6H4, R 9 for n is 0.
8. The use of the benzo[a] polycyclic compound of any one of claims 1-7 or its agriculturally chemically acceptable salt, hydrate, solvate, or its enantiomer or optically active derivative as an HPPD inhibitor in the control of weeds; Preferably, the weeds are selected from at least one of broadleaf weeds, grass weeds, and sedges.
9. An HPPD-inhibiting herbicide, characterized in that, The herbicide contains an effective amount of active ingredient for weed control, said active ingredient including any one of the benzo[a] polycyclic compound as described in any one of claims 1-7, or its agriculturally chemically acceptable salt, hydrate, solvate, or its enantiomer or optically active derivative; Preferably, the herbicide formulation is selected from at least one of wettable powder, soluble powder, emulsifiable concentrate, aqueous suspension, dispersible oil suspension, water emulsion, microemulsion, soluble liquid, or water-dispersible granules.
10. The herbicide according to claim 9, characterized in that, This herbicide also contains a herbicide safener; Preferably, the herbicide safener comprises at least one of 1,8-naphthalenedicarboxylic anhydride, dichloropropeneamine, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, furazolidone, cyclohexane, pyrazosulfuron, bis(oxazolyl) acid, cyclopropanesulfonamide, brassinolide, allyl oxychloride, and oxadiazon.