A phenyl trifluoroethyl sulfide (sulfoxide) compound and use thereof

Abstract

The present invention relates to phenyl trifluoroethyl sulfide (sulfoxide) compounds of formula (I) wherein n, R 1 , R 2 , R 3 , R 4 , R 5 , X, Y are each as defined in the specification, to their use as acaricides and insecticides for controlling animal pests, and to processes for their preparation.

Description

Technical Field

[0001] This invention relates to a phenyltrifluoroethyl sulfide (sulfoxide) compound and its uses. Specifically, it relates to the use of phenyltrifluoroethyl sulfide (sulfoxide) compounds for controlling animal pests, and methods for preparing such compounds. This invention also relates to pesticide compositions comprising said phenyltrifluoroethyl sulfide (sulfoxide) compounds. Background Technology

[0002] Invertebrate pests are highly destructive to crop growth, causing not only economic losses but also threatening the normal food supply for humans. Although humans have developed a large number of pesticides, pests can quickly develop resistance to these pesticides. Therefore, humans still need to continuously develop new pesticides.

[0003] Existing patent document 1 (CN104125773A) discloses N-arylamidinium-substituted trifluoroethyl sulfide derivatives (structural formula shown below) and their use in controlling related pests.

[0004]

[0005] Existing patent document 2 (CN102341376A) discloses a 3-arylquinazolin-4-one compound (structure shown below) for the control of invertebrate pests, and also describes that this type of compound has good activity against diamondback moth, silver leaf whitefly, two-spotted spider mite, etc.

[0006]

[0007] Existing patent document 3 (CN111978225A) discloses a class of trifluoroethyl sulfide (sulfoxide) substituted benzene compounds (the structural formula is shown below), and the specification describes the excellent activity of this class of compounds against related mite pests.

[0008]

[0009] The long-term use of these existing compounds as insecticides and acaricides will lead to significant resistance in pests and mites, increasing the difficulty of pest control and seriously threatening the healthy growth of crops. Therefore, it is necessary to continuously develop new and highly effective insecticides and acaricides. Summary of the Invention

[0010] The purpose of this invention is to provide a class of phenyltrifluoroethyl sulfide (sulfoxide) compounds that have excellent control effects on pests and mites. They have high insecticidal and acaricidal activity even when applied in small doses, and have high selectivity and compatibility with plant crops. They can be widely used in the control of pests and mites in agriculture, forestry and health fields.

[0011] This invention provides a phenyltrifluoroethyl sulfide (sulfoxide) compound of formula (I):

[0012]

[0013] in:

[0014] n is selected from 0 or 1;

[0015] R 1 Selected from aldehyde, hydroxyl, nitro, cyano, halogen, optionally substituted alkyl or optionally substituted alkoxy groups;

[0016] R 2 R 3 They may be the same or different, and each is independently selected from hydrogen, hydroxyl, nitro, cyano, halogen, optionally substituted alkyl or optionally substituted alkoxy;

[0017] R 4 R 5 They may be the same or different, each independently selected from hydrogen, optionally substituted alkyl groups, R 4 R 5 Carbon atoms that can be bonded together with them can form rings;

[0018] X and Y can be the same or different, and each can be independently selected from CO or CH2;

[0019] And diastereomers, enantiomers and rotational isomers of compounds of formula (I).

[0020] The present invention also provides methods for preparing diastereomers, enantiomers and rotational isomers of the compound of formula (I).

[0021] The present invention also discloses a pesticide composition containing a compound of formula (I).

[0022] Furthermore, this invention also discloses a method for controlling pests and mites using the compound of formula (I). Detailed Implementation

[0023] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention. Unless otherwise expressly stated, throughout the specification and claims, the term "comprising" or its variations such as "including" or "comprising of," etc., will be understood to include the stated components or steps, without excluding other substances or steps.

[0024] Furthermore, to better illustrate the present invention, numerous specific details are provided in the following detailed embodiments.

[0025] Those skilled in the art will understand that the present invention can be practiced even without certain specific details. In some embodiments, materials, methods, and means well known to those skilled in the art are not described in detail in order to highlight the spirit of the invention.

[0026] In this invention, C n ~C m The subscript indicates the number of carbon atoms in the group in all cases; halogen indicates fluorine, chlorine, bromine and iodine in all cases.

[0027] As used herein, the term "alkyl" (and in other alkyl groups, such as alkoxy groups) in each case means a straight-chain or branched alkyl group generally having 1 to 10 carbon atoms, often 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and especially 1 to 3 carbon atoms. Examples of C1 to C4 alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), and 1,1-dimethylethyl (tert-butyl). Examples of C1-C6 alkyl groups, in addition to those mentioned for C1-C4 alkyl groups, include n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl. C1-C 10 Examples of alkyl groups, in addition to those mentioned for C1 to C6 alkyl groups, include n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl, 2-propylpentyl, nonyl, decyl, 2-propylheptyl, and 3-propylheptyl.

[0028] The term "optional substitution" means that the relevant group may or may not be substituted by a substituent.

[0029] When a relevant group (such as an alkyl group) is replaced by a substituent, the substituent can be a hydroxyl, cyano, nitro, amino, or halogen. When an alkyl group is replaced by a halogen, a haloalkyl group is formed.

[0030] The term "haloalkyl" as used herein (and in other groups containing alkyl halides, such as alkoxy halides) in each case means generally having 1 to 10 carbon atoms ("C1 to C2"). 10 The term "haloalkyl" refers to a straight-chain or branched alkyl group with 1 to 6 carbon atoms ("C1-C6 haloalkyl"), more commonly 1 to 4 carbon atoms ("C1-C4 haloalkyl"), wherein some or all of the hydrogen atoms in the group are substituted with halogens. Preferred haloalkyl structural moieties are selected from C1-C4 haloalkyl, more preferably C1-C2 haloalkyl, and even more preferably halomethyl, especially C1-C2 fluoroalkyl. A halomethyl group is a methyl group in which 1, 2, or 3 hydrogen atoms are substituted with halogens, examples of which include bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloromonofluoromethyl, and monochlorodifluoromethyl. Examples of C1-C2 fluoroalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, and 2,2-fluoromethyl. Examples of C1-C2 haloalkyl groups, in addition to the groups mentioned in C1-C2 fluoroalkyl groups, include chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chlorofluoromethyl, dichloromonofluoromethyl, monochlorodifluoromethyl, 1-chloroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-bromoethyl, etc. Examples of C1-C4 haloalkyl groups, in addition to the groups mentioned in C1-C2 haloalkyl groups, include 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoropropyl-2-yl, 3-chloropropyl, 4-chlorobutyl, etc.

[0031] The term "cyclo" or "cycloalkyl" in this invention generally refers to a structure having 3 to 10 carbon atoms ("C3-C4"). 10 Cycloalkyl groups, preferably monocyclic or bicyclic alicyclic groups with 3 to 7 carbon atoms (“C3-C7 cycloalkyl”), especially 3 to 6 carbon atoms (“C3-C6 cycloalkyl”). Examples of monocyclic groups with 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of monocyclic groups with 3 to 7 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. Examples of bicyclic groups with 7 or 8 carbon atoms include bicyclic [2.1.1]hexyl, bicyclic [3.1.1]heptyl, bicyclic [2.2.1]heptyl, bicyclic [2.2.2]octyl, and bicyclic [3.2.1]octyl.

[0032] In this invention, the term "amino" refers to NR6R7, where R6 and R7 are each independently selected from hydrogen and alkyl groups, such as amino, methylamino, ethylamino, n-propylamino, isopropylamino, dimethylamino, diethylamino, di-n-propylamino, and diisopropylamino.

[0033] In this invention, the term "aldehyde group" refers to a nailyl acyl group or -CHO.

[0034] The following description of the variables of the compound of formula (I) and the preferred embodiments of the variables, the features of the use and method of the present invention, and the features of the compositions of the present invention are effective either on their own or in preferred combinations thereof.

[0035] The present invention provides a phenyltrifluoroethyl sulfide (sulfoxide) compound of formula (I):

[0036]

[0037] in:

[0038] n is selected from 0 or 1;

[0039] R 1 Selected from aldehyde, hydroxyl, nitro, cyano, halogen, optionally substituted alkyl or optionally substituted alkoxy groups;

[0040] R 2 R 3 They may be the same or different, and each is independently selected from hydrogen, hydroxyl, nitro, cyano, halogen, optionally substituted alkyl or optionally substituted alkoxy;

[0041] R 4 R 5 They may be the same or different, each independently selected from hydrogen, optionally substituted alkyl groups, R 4 R 5 Carbon atoms that can be bonded together with them can form rings;

[0042] X and Y can be the same or different, and each can be independently selected from CO or CH2;

[0043] And diastereomers, enantiomers and rotational isomers of compounds of formula (I).

[0044] The present invention also provides methods for preparing diastereomers, enantiomers and rotational isomers of the compound of formula (I).

[0045] Depending on the substitution mechanism, compounds of formula (I) may have one or more chiral centers, in which case they exist as enantiomers or mixtures thereof. This invention provides the use of pure enantiomers or diastereomers or mixtures thereof, as well as the use of pure enantiomers or diastereomers or mixtures thereof of compounds of formula (I). Suitable compounds of formula (I) also include all possible rotational isomers and mixtures thereof.

[0046] According to one embodiment of the present invention, X in the compound of formula (I) is CO.

[0047] According to one embodiment of the present invention, X in the compound of formula (I) is CH2.

[0048] According to one embodiment of the present invention, Y in the compound of formula (I) is CO.

[0049] According to one embodiment of the present invention, Y in the compound of formula (I) is CH2.

[0050] According to one embodiment of the present invention, X and Y in the compound of formula (I) are both CO.

[0051] According to one embodiment of the present invention, X and Y in the compound of formula (I) are both CH2.

[0052] According to a preferred embodiment of the present invention, R in compound (I) 1 It is selected from optionally substituted alkyl, optionally substituted alkoxy, aldehyde, hydroxy, cyano, amino, nitro or halogen.

[0053] According to another preferred embodiment of the present invention, R in compound (I) 1 Selected from C1 to C1 by optional substitution 10 Alkyl groups, or optionally substituted C1-C1 groups 10 Alkoxy, aldehyde, hydroxy, cyano, amino, nitro, or halogen.

[0054] According to another preferred embodiment of the present invention, R in compound (I) 1 Selected from the substituted C1 to C 10 Alkyl, substituted C1-C 10 The substituted group is alkoxy, aldehyde, hydroxy, cyano, amino, nitro, or halogen, wherein the substituent is hydroxy, cyano, nitro, amino, or halogen.

[0055] According to another preferred embodiment of the present invention, R in compound (I) 1 Selected from C1 to C 10 Alkyl, C1-C 10 Alkoxy, aldehyde, hydroxy, cyano, amino, nitro, or halogen.

[0056] According to another preferred embodiment of the present invention, R in compound (I) 1 The group is selected from substituted C1-C6 alkyl, substituted C1-C6 alkoxy, aldehyde, hydroxyl, cyano, amino, nitro or halogen, wherein the substituted substituent is hydroxyl, cyano, nitro, amino or halogen.

[0057] According to another preferred embodiment of the present invention, R in compound (I) 1 It is selected from C1-C6 alkyl, C1-C6 alkoxy, aldehyde, hydroxyl, cyano, amino, nitro or halogen.

[0058] According to another preferred embodiment of the present invention, R in compound (I) 1 The group is selected from substituted C1-C4 alkyl groups, substituted C1-C4 alkoxy groups, aldehyde groups, hydroxyl groups, cyano groups, amino groups, nitro groups, or halogens, wherein the substituted substituents are hydroxyl, cyano, nitro, amino, or halogens.

[0059] According to another preferred embodiment of the present invention, R in compound (I) 1 It is selected from C1-C4 alkyl, C1-C4 alkoxy, aldehyde, hydroxyl, cyano, amino, nitro or halogen.

[0060] According to a particularly preferred embodiment of the present invention, R in compound (I) 1 It is selected from methyl, methoxy, aldehyde, hydroxy, cyano, amino, nitro or halogen, where the halogen is selected from fluorine, chlorine and bromine.

[0061] According to another preferred embodiment of the present invention, R in compound (I) 2 R 3 They may be the same or different, each independently selected from hydrogen, hydroxyl, cyano, nitro, amino, halogen, optionally substituted alkyl or optionally substituted alkoxy.

[0062] According to another preferred embodiment of the present invention, R in compound (I) 2 R 3 They can be the same or different, and each can be independently selected from hydrogen, hydroxyl, cyano, nitro, amino, halogen, or substituted C1 to C2 groups. 10 Alkyl, substituted C1-C 10 Alkoxy, wherein the substituent is hydroxyl, cyano, nitro, amino, or halogen.

[0063] According to another preferred embodiment of the present invention, R in compound (I) 2 R 3 They can be the same or different, and each can be independently selected from hydrogen, hydroxyl, cyano, nitro, amino, halogen, C1-C2. 10 Alkyl, C1-C 10 Alkyl group.

[0064] According to another preferred embodiment of the present invention, R in compound (I) 2 R 3 They may be the same or different, and each can be independently selected from hydrogen, hydroxyl, cyano, nitro, amino, halogen, substituted C1-C6 alkyl, substituted C1-C6 alkoxy, wherein the substituents are hydroxyl, cyano, nitro, amino and halogen.

[0065] According to another preferred embodiment of the present invention, R in compound (I) 2 R 3 They can be the same or different, and each can be independently selected from hydrogen, hydroxyl, cyano, nitro, amino, halogen, C1-C6 alkyl, and C1-C6 alkoxy.

[0066] According to another preferred embodiment of the present invention, R in compound (I) 2 R 3 They may be the same or different, and each can be independently selected from hydrogen, hydroxyl, cyano, nitro, amino, halogen, substituted C1-C4 alkyl, substituted C1-C4 alkoxy, wherein the substituents are hydroxyl, cyano, nitro, amino and halogen.

[0067] According to another preferred embodiment of the present invention, R in compound (I) 2 R 3 They can be the same or different, and each can be independently selected from hydrogen, hydroxyl, cyano, nitro, amino, halogen, C1-C4 alkyl, and C1-C4 alkoxy.

[0068] According to a particularly preferred embodiment of the present invention, R in compound (I) 2 R 3 Selected from hydrogen.

[0069] According to another preferred embodiment of the present invention, R in compound (I) 4 R 5 They can be the same or different, and each can be independently selected from hydrogen, substituted C1 to C2. 10 Alkyl groups, wherein the substituents are hydroxyl, cyano, nitro, amino, and halogen.

[0070] According to another preferred embodiment of the present invention, R in compound (I) 4 R 5 They can be the same or different, and each can be independently selected from hydrogen, C1 to C2. 10 alkyl.

[0071] According to another preferred embodiment of the present invention, R in compound (I) 4 R 5They may be the same or different, and each can be independently selected from hydrogen, substituted C1 to C6 alkyl groups, wherein the substituents are hydroxyl, cyano, nitro, amino, and halogen.

[0072] According to another preferred embodiment of the present invention, R in compound (I) 4 R 5 They can be the same or different, and each can be independently selected from hydrogen and C1 to C6 alkyl groups.

[0073] According to another preferred embodiment of the present invention, R in compound (I) 4 R 5 They may be the same or different, and each can be independently selected from hydrogen, substituted C1 to C4 alkyl groups, wherein the substituted substituents are hydroxyl, cyano, nitro, amino, and halogen.

[0074] According to another preferred embodiment of the present invention, R in compound (I) 4 R 5 They can be the same or different, and each can be independently selected from hydrogen and C1 to C4 alkyl groups.

[0075] According to a particularly preferred embodiment of the present invention, R in compound (I) 4 R 5 They can be the same or different, and each can be independently selected from H, methyl, ethyl, propyl, and butyl.

[0076] According to a particularly preferred embodiment of the present invention, R in compound (I) 4 and R 5 The carbon atoms that are connected to them form a ring, wherein the ring is C3 to C4. 10 ring.

[0077] According to a particularly preferred embodiment of the present invention, R in compound (I) 4 and R 5 The carbon atoms that are connected to them form a ring, which is a C3 to C7 ring.

[0078] According to a particularly preferred embodiment of the present invention, R in compound (I) 4 and R 5 The carbon atoms that are connected to them form a ring, which is a C3 to C6 ring.

[0079] According to a particularly preferred embodiment of the present invention, n in the compound of formula (I) is selected from 0 or 1.

[0080] According to a particularly preferred embodiment of the present invention, n in the compound of formula (I) is selected from 0.

[0081] According to a particularly preferred embodiment of the present invention, n in the compound of formula (I) is selected from 1.

[0082] Another aspect of the present invention provides a method for preparing a compound of formula (I), comprising the following steps:

[0083] Compound (II) is condensed in one step with compound (III) or its salt to form compound (I);

[0084] Or, compound (II) and compound (III) or their ammonium salt are converted stepwise into compound (I) via intermediates of formula (IV) and / or formula (V);

[0085] In formulas (I), (IV) and (V), n = 0 can be converted to n = 1 through oxidation, and X and / or Y = CO can be converted to X and / or Y = CH2 through reduction.

[0086] Where, n, R 1 R 2 R 3 R 4 R 5 X and Y are defined as above; LG is a leaving group, preferably one of Cl, Br, OTs, OMs, or OBs.

[0087] Its main reaction equations are as follows:

[0088]

[0089] In the above reactions, compound (II) can be prepared according to the methods reported in WO9954324, WO2007052383, or WO2004113295. Compounds (III) and (VI) can be prepared according to the methods reported in WO2013092350, WO2014095979, WO2018015852, or US9981940.

[0090] In the above reactions, during the preparation of formula (I) by reactions (II) and (III): the reaction can be carried out by heating at 100-250°C, or by adding a suitable acid, such as H3PO4, H2SO4, TsOH, HCl, AcOH, but not limited to these, to promote the reaction.

[0091] In the above reactions, during the preparation of formula (IV) using formulas (II) and (III): the reaction can be carried out by heating at 100–250 °C, and adjusting the reaction temperature and time can yield the intermediate (IV) before cyclization. Alternatively, adding a suitable acid, such as H3PO4, H2SO4, TsOH, HCl, AcOH, but not limited to these, can promote the reaction. Or adding a suitable base, such as Na2CO3, NaHCO3, K2CO3, KHCO3, LDA, AlMe3, but not limited to these, can also promote the reaction.

[0092] In the above reaction, during the preparation of formula (I) by reaction (IV): the reaction can be carried out by heating at 100-250°C, or by adding a suitable acid, such as H3PO4, H2SO4, TsOH, HCl, AcOH, but not limited to these, to promote the reaction.

[0093] In the above reaction, during the preparation of formula (V) by reaction (IV): OH can be converted to Cl or Br by halogenating agents such as SOCl2, PCl3 or PBr3, but not limited thereto; or OH can be converted to the corresponding sulfonyl ester by suitable sulfonyl chlorides such as TsCl, MsCl or BsCl, but not limited thereto.

[0094] In the above reaction, during the preparation of formula (I) by reaction (V): the reaction can be carried out by adding a base, such as TEA, NaOMe, NaOEt, Na2CO3, NaHCO3, K2CO3, KHCO3, etc., but not limited to these, and the reaction is carried out at 0 to 150℃.

[0095] In the above reactions, n=0 in formulas (I), (IV) and (V) is changed to n=1: This reaction can be achieved through an oxidation reaction using oxidizing agents such as H2O2, NaOCl, mCPBA, etc., but not limited to these.

[0096] In the above reactions, X and / or Y = CO in formulas (I), (IV) and (V) are converted to X and / or Y = CH2. This reaction can be achieved through a reduction reaction using a reducing agent, such as red phosphorus, zinc powder, LiAlH4, etc., but not limited to these.

[0097] The present invention also includes another method for preparing the compound of formula (I), the main reaction formula of which is as follows:

[0098]

[0099] In this case, the compound of formula (II) is condensed in one step with the compound of formula (VI) or its salt to form the compound of formula (VII), and the conversion is carried out by a method similar to that described above;

[0100] Wherein, compound (II) and compound (VI) or their salts are converted into compound (VII) via intermediates of formula (VIII) and / or formula (IX), and the conversion is carried out by a method similar to that described above;

[0101] Then, referring to the methods reported in WO2013092350, WO2014095979, WO2018015852 or US9981940, the compound of formula (VII) was converted into the compound of formula (I).

[0102] In equation (I), n = 0 can be converted to n = 1 through an oxidation reaction, and the conversion can be carried out by a method similar to that described above.

[0103] In formulas (I), (VII), (VIII) and (IX), X and / or Y = CO can be converted into X and / or Y = CH2 via a reduction reaction, and the conversion is carried out by a method similar to that described above.

[0104] The definitions of n, R1, R2, R3, R4, R5, X, Y, and LG are as above.

[0105] Because the compounds of formula (I) of this invention possess excellent acaricidal and insecticidal activities, they are suitable for plant protection and animal pest control in agriculture, forestry, and horticulture. The harmful organisms to which the compounds of this invention are effective include, for example, harmful mites and nematodes. Specific examples of harmful organisms include the following pests (the listed objects are for illustrative purposes only and do not limit the scope of protection of this invention):

[0106] Arachnida, such as the genera *Tetranychus*, *Rhizoctonia*, *Citrus galliseptica*, *Hemiptera*, *Bruciformis*, *Tetranychus*, and *Ophiocorhiza*.

[0107] Lepidoptera pests, such as diamondback moth, armyworm, beet armyworm, cotton bollworm, tobacco bollworm, rice stem borer, rice leaf roller, corn borer, and cotton bollworm.

[0108] Homoptera pests, such as bean aphids, cotton aphids, apple aphids, peach aphids, corn aphids, whiteflies, and rice planthoppers.

[0109] Coleoptera, including genera such as leaf beetles, round-skinned beetles, root-necked beetles, flea beetles, bean beetles, star-shaped longhorn beetles, bean leaf beetles, tortoise beetles, black longhorn beetles, and spider beetles.

[0110] The class Helminthiae includes species such as *C. cucurbita*, *C. trichomonas*, *C. heterochila*, *C. ascarid*, and *C. nodosa*.

[0111] Orthoptera, such as the Oriental cockroach.

[0112] Diptera, such as the genera *Anopheles*, *Fructus*, *Corydalis*, *Honeyfly*, and *Vibrio*.

[0113] Plant parasitic nematodes, such as those in the genera *Stem Nematode*, *Heterodera*, *Longnematode*, and *Short-bodied Nematode*.

[0114] The compound of formula (I) of the present invention can control pests by means of an effective amount of the active compound, or by use in pest-infested plants, seeds, materials or soil.

[0115] Insecticidal compositions typically contain 0.1–95 wt%, preferably 0.5–90 wt%, of the compound of formula (I). When reagents containing the compounds of the present invention are used to control pests such as insects and mites, the application rate based on the compound of formula (I) of the present invention is typically selected as 10–1000 g per hectare, preferably an effective amount of 20–500 g per hectare. When pesticide compositions containing the compound of formula (I) are used to control pests in formulations such as emulsifiable concentrates, wettable powders, or microemulsions, they are typically applied by diluting these formulations with water to a concentration of the active ingredient [i.e., the compound of formula (I)] in the range of 0.01–5000 ppm. Studies have shown that granules or powders can be applied without dilution. Research results indicate that the compound of formula (I) of the present invention has a mortality rate of at least 90% against certain pests in the range of concentrations from 0.01 to 100 ppm (0.01 mg / L to 100 mg / L). Preferred compounds exhibit at least 90% lethality against certain pests in the range of 0.01 ppm to 10 ppm. Particularly preferred compounds exhibit at least 90% lethality against certain pests in the range of 0.01 ppm to 0.5 ppm.

[0116] Compounds of formula (I) can be formulated into conventional preparations using conventional methods, such as emulsifiable concentrates, oil solutions, powders, granules, wettable powders, flowable concentrates, microcapsules, aerosols, smoke generators, poison baits, etc. The form of use depends on the specific purpose.

[0117] The formulation is prepared using conventional and known methods, such as by mixing the active compound with a solvent and / or a carrier, and, if necessary, by adding suitable emulsifiers and dispersants or other commonly used adjuvants.

[0118] The reagents for controlling pests of the present invention comprise the compounds of the present invention and an inert carrier. As used herein, an inert carrier refers to a expander, a diluent, and other formulations used in disease control and agriculture. The reagents for controlling pests of the present invention are typically prepared by mixing the compounds of the present invention with an inert carrier, such as a solid carrier, a liquid carrier, or a gaseous carrier, and, if desired, by adding surfactants and other formulation adjuvants to produce emulsifiable concentrates, oil solutions, powders, granules, wettable powders, flowables, microcapsules, aerosols, fumigants, poison baits, etc.

[0119] Examples of solid carriers used in pesticide composition support formulations include: fine powders or granules of clay (e.g., kaolin clay, diatomaceous earth, bentonite), synthetic hydrated silica, talc, ceramics, other inorganic materials (e.g., quartz, sulfur, activated carbon, calcium carbonate, or hydrated silica), chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, or ammonium chloride), and synthetic resins (e.g., polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate and polyethylene terephthalate, nylon resins, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer), etc.

[0120] Examples of the aforementioned liquid carriers include: water, alcohols (e.g., methanol, ethanol, isopropanol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, or phenoxyethanol), ketones (e.g., acetone, methyl ethyl ketone, or cyclohexanone), aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, or methylnaphthalene); aliphatic hydrocarbons (e.g., hexane, cyclohexane, kerosene, or light oil), esters (e.g., ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, or propylene glycol). Alcohol monomethyl ether acetate, propylene carbonate), nitrile (e.g., acetonitrile or isobutyronitrile), ether (e.g., diisopropyl ether, 1,4-diane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether or 3-methoxy-3-methyl-1-butanol), amide (e.g., N,N-dimethylformamide or N,N-dimethylacetamide), halogenated hydrocarbons (e.g., dichloromethane, trichloroethane or carbon tetrachloride), sulfoxides (e.g., dimethyl sulfoxide), and vegetable oils (e.g., soybean oil or cottonseed oil).

[0121] Examples of the aforementioned gas carriers include butane gas, liquefied petroleum gas, dimethyl ether, and carbon dioxide gas.

[0122] The surfactants used in this invention include: nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyethylene glycol fatty acid esters, and anionic surfactants such as alkyl sulfonates / benzene sulfonates / sulfates.

[0123] Examples of other formulation adjuvants that may be added as needed include: binders, dispersants, colorants, and stabilizers. Specific examples include starch, gum arabic, cellulose derivatives and alginic acid, lignin derivatives, bentonite, polyvinyl alcohol, polyvinylpyrrolidone and polyacrylic acid, and mixtures of 2,6-di-tert-butyl-4-cresol, 2-tert-butyl-4-methoxyphenol, and 3-tert-butyl-4-methoxyphenol.

[0124] The prepared formulation typically contains 0.01 to 95 wt%, preferably 0.1 to 90 wt%, of an active compound.

[0125] The concentration of the active compound in the ready-to-use formulation can vary over a wide range, for example, from 0.0001 to 10 wt%.

[0126] The pesticide reagent of the present invention for controlling pests can be used in farmland containing the following plants. The plants mentioned include: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beets, rapeseed, sunflowers, sugarcane, tobacco, eggplant, tomato, bell peppers, chili peppers, potatoes, cucumbers, pumpkins, zucchini, watermelons, cantaloupes, Japanese radishes, white radishes, horseradishes, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, garland chrysanthemum, artichokes, lettuce, scallions, onions, garlic, or asparagus, carrots, parsley, celery, parsnip, spinach, Swiss chard, apples, pears, papayas, peaches, plums, nectarines, prunes, cherries, apricots, prunes, Satsuma mandarins, oranges, lemons, limes, grapefruits, chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, or macadamia nuts, grapes, persimmons, olives, loquats, bananas, coffee, dates, coconut palms, oil palms, etc. The above-mentioned plants include their genetically modified forms.

[0127] Preparation Examples

[0128] The preparation and application of the active ingredient of formula (I) of the present invention are illustrated by the following examples, but are not limited to these examples. The raw materials used in the preparation examples of the present invention can be obtained commercially or synthesized by referring to methods disclosed in the prior art.

[0129] Example 1

[0130]

[0131] 2-Fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)aniline (III-1, 25.5 g, 0.1 mol, 1 equiv), 6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2-one (II-1, 15.1 g, 0.12 mol, 1.2 equiv), and p-toluenesulfonic acid (172 mg, 1 mmol, 1 mol%) were added to a 100 mL reaction flask. The mixture was heated to 180 °C and stirred for 24 h. The mixture was then cooled to room temperature. Toluene (160 mL) was added, and the mixture was stirred at 0 °C for 2 h. The mixture was filtered, rinsed with toluene (40 mL), saturated NaHCO3 (40 mL), and deionized water (100 mL). The filter cake was dried by forced air at 60°C to give 31.2 g of a yellow solid 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-one (I-1), yield 86%, HPLC purity 97.5%. LC-MS (m / z, ESI): 364.1 (M+H) + 386.0 (M+Na) + .

[0132] Example 2

[0133]

[0134] 2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)aniline (III-1, 23.9 g, 0.1 mol, 1 equiv), 6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2-one (II-1, 15.1 g, 0.12 mol, 1.2 equiv), and p-toluenesulfonic acid (172 mg, 1 mmol, 1 mol%) were added to a 100 mL reaction flask. The mixture was heated to 180 °C and stirred for 24 h. The mixture was then cooled to room temperature. Toluene (150 mL) was added, and the mixture was stirred at 0 °C for 2 h. The mixture was filtered, rinsed with toluene (30 mL), saturated NaHCO3 (40 mL), and deionized water (100 mL). The filter cake was dried by forced air at 60°C to give 27.4 g of a yellow solid 3-(2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-one (I-88), with a yield of 79% and an HPLC purity of 98.3%. LC-MS (m / z, ESI): 348.1 (M+H) + 370.2 (M+Na) + .

[0135] Example 3

[0136]

[0137] 3-(2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-one (I-15, 24.3 g, 70 mmol, 1 equiv) was dissolved in dichloromethane (100 mL). m-CPBA (85% purity, 17.1 g, 84 mmol, 1.2 equiv) was added at 0–10 °C. The mixture was stirred at 0–10 °C for 18 h. The reaction was quenched by adding sodium sulfite (3.5 g, 28 mmol, 0.4 equiv) and water (20 mL) at 0–10 °C. The mixture was separated, and the organic phase was washed once each with saturated NaHCO3 (100 mL) and water (50 mL). The organic phase was concentrated to dryness to give 24.9 g of a yellow solid 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-one (I-1), yield 98%, HPLC purity 98.5%. LC-MS (m / z, ESI): 364.1 (M+H) + 386.0 (M+Na) + .

[0138] Example 4

[0139]

[0140] Add 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)aniline (III-1, 25.5 g, 0.1 mol, 1 equiv), 6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2-one (II-1, 13.3 g, 0.105 mol, 1.05 equiv), and xylene (200 mL) to a 500 mL reaction flask. Heat to 140 °C and stir for 24 h. Cool to 0 °C to crystallize for 2 h, filter, and wash with xylene (40 mL). Dry at 60 °C to give 34.7 g of yellow solid N-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-3-hydroxymethyl-2,2-dimethylcyclopropane-1-amide (IV-1), yield 91%, HPLC purity 98.7%. LC-MS (m / z, ESI): 382.1 (M+H) + 404.1(M+Na) + .

[0141] Example 5

[0142]

[0143] N-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-3-hydroxymethyl-2,2-dimethylcyclopropane-1-amide (IV-1, 25 g, 65.5 mmol, 1 equiv) and p-toluenesulfonyl chloride (13.1 g, 68.8 mmol, 1.05 equiv) were dissolved in DCM (200 mL) and cooled to -5 °C. Triethylamine (7.3 g, 72.1 mmol, 1.1 equiv) was added dropwise, and the temperature was controlled between -5 and 5 °C. After the addition was complete, the reaction was carried out at -5 to 5 °C for 6 h. The reaction solution was washed with water (70 mL), saturated NaHCO3 (70 mL), and water (70 mL). The organic phase was concentrated to dryness to give 32.7 g of a yellow solid, 3-((2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)carbamoyl-2,2-dimethylcyclopropyl)methanol-p-toluenesulfonate (V-1), with a yield of 93% and an HPLC purity of 96.6%. LC-MS (m / z, ESI): 536.2 (M+H) + 558.1(M+Na) + .

[0144] Example 6

[0145]

[0146] 3-((2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)carbamoyl-2,2-dimethylcyclopropyl)methanol-p-toluenesulfonate (V-1, 20 g, 37.3 mmol, 1 equiv) and triethylamine (4.5 g, 44.8 mmol, 1.2 equiv) were dissolved in dichloroethane (150 mL) and heated to reflux for 16 h. The mixture was cooled to room temperature, washed with water (70 mL), 1 M hydrochloric acid (70 mL), and saturated NaHCO3 (70 mL). The organic phase was concentrated to dryness. Toluene (40 mL) was added to the residue and the mixture was stirred at 0 °C for 2 h. The mixture was filtered and washed with toluene (10 mL). The solution was dried at 60 °C to give 11.1 g of a yellow solid, 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-one (I-1), with a yield of 82% and an HPLC purity of 97.5%. LC-MS (m / z, ESI): 364.1 (M+H) + 386.0 (M+Na) + .

[0147] Example 7

[0148]

[0149] N-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethylthio)phenyl)-3-hydroxymethyl-2,2-dimethylcyclopropane-1-amide (IV-2, 27 g, 73.9 mmol, 1 equiv) and 85% phosphoric acid (0.43 g, 3.7 mmol, 5 mol%) were added to xylene (120 mL), and the mixture was heated to reflux for 24 h. After cooling to room temperature, the mixture was washed with water (60 mL) and then with saturated NaHCO3 (6 mL). 0 mL). The organic phase was cooled to 0 °C and slurried for 2 h. Filtered and washed with xylene (10 mL). Drying at 60 °C, yielding 24.1 g of a yellow solid 3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethylthio)phenyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-one (I-88), yield 94%, HPLC purity 97.9%. LC-MS (m / z, ESI): 348.1 (M+H) + 370.1 (M+Na) + .

[0150] Example 8

[0151]

[0152] 2-Fluoro-4-chloro-5-((2,2,2-trifluoroethyl)sulfinyl)aniline (III-2, 14 g, 50.8 mmol, 1 equiv), 6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2-one (II-1, 7.7 g, 61 mmol, 1.2 equiv), and 98% sulfuric acid (51 mg, 0.51 mmol, 1 mol%) were added to a 100 mL reaction flask. The mixture was heated to 150 °C and stirred for 24 h. The mixture was then cooled to room temperature. Toluene (80 mL) was added, and the mixture was stirred at 0 °C for 2 h. The mixture was filtered, rinsed with toluene (20 mL), saturated NaHCO3 (40 mL), and deionized water (50 mL). The filter cake was dried by forced air at 60°C to give 15.2 g of a yellow solid 3-(2-fluoro-4-chloro-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-one (I-8), with a yield of 78% and an HPLC purity of 97.8%. LC-MS (m / z, ESI): 384.0 (M+H) + 406.1 (M+Na) + .

[0153] Example 9

[0154]

[0155] 2-Fluoro-4-methylaniline (VI-1, 50 g, 0.4 mol, 1 equiv), 6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2,4-dione (II-2, 67.2 g, 0.48 mol, 1.2 equiv), p-toluenesulfonic acid (827 mg, 4.8 mmol, 1 mol%), and toluene (250 mL) were added to a 500 mL reaction flask. The mixture was refluxed to remove water for 24 h. The mixture was then cooled to 0 °C and stirred for 2 h. After filtration, the mixture was rinsed with toluene (50 mL), saturated NaHCO3 (100 mL), and deionized water (100 mL). The filter cake was dried by forced air at 60°C to give 87.0 g of a yellow solid 3-(2-fluoro-4-methylphenyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,4-dione (VII-1), with a yield of 88% and an HPLC purity of 98.6%. LC-MS (m / z, ESI): 284.1 (M+H) + 270.1 (M+Na) + .

[0156] Example 10

[0157]

[0158] 5-(6,6-dimethyl-2,4-dioxo-3-azabicyclo[3.1.0]-3-hexyl)-4-fluoro-2-methylbenzenesulfonyl chloride (X-1, 11 g, 31.8 mmol, 1 equiv) was dissolved in glacial acetic acid (250 mL) and heated to reflux. Zn powder (16.6 g, 254 mmol, 8 equiv) was added in portions. After the addition was complete, reflux was continued for 3 h. Water (250 mL) was added, and reflux was continued for 3 h. The mixture was cooled to room temperature. The mixture was concentrated to dryness under reduced pressure, and the residue was extracted three times with EA (70 mL * 3) with water (250 mL). The organic phase was washed with saturated NaHCO3 (250 mL) and water (250 mL). The organic phase was concentrated to dryness. The residue was added to xylene (50 mL) and stirred at 0 °C for 2 h, filtered, and washed with xylene (10 mL). The filter cake was dried by forced air at 60°C to obtain 6.3 g of a brown solid, 3-(2-fluoro-5-mercapto-4-methylphenyl)-6,6-dimethyl-3-azabicyclo[3.1.0]-2-hexanone (XI-1), with a yield of 75% and an HPLC purity of 95.7%. LC-MS (m / z, ESI): 266.1 (M+H) + 288.1 (M+Na) + .

[0159] Example 11

[0160]

[0161] 2-Fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)aniline (III-1a, 7.5 g, 29.4 mmol, 1 equiv), (1R,5S)-6,6-dimethyl-3-oxabicyclo[3.1.0]hexane-2-one (II-1, 4.4 g, 34.9 mmol, 1.2 equiv), and p-toluenesulfonic acid (52 mg, 0.3 mmol, 1 mol%) were added to a 50 mL reaction flask. The mixture was heated to 180 °C and stirred for 24 h. The mixture was then cooled to room temperature. Toluene (40 mL) was added, and the mixture was stirred at 0 °C for 2 h. The mixture was filtered, rinsed with toluene (8 mL), saturated NaHCO3 (20 mL), and deionized water (40 mL). The filter cake was dried by forced air at 60°C to give 8.7 g of a yellow solid (1R,5S)-3-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-one (I-1a), with a yield of 82% and an HPLC purity of 97.7%. LC-MS (m / z, ESI): 364.1 (M+H) + 386.0 (M+Na) + .

[0162] Compound of formula (I) in this invention was prepared by a method similar to that described in the above embodiments, as shown in Table 1.

[0163] Table 1

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171] Bioactivity assay

[0172] The insecticidal activity of the compounds of this invention against relevant pests was determined by experiments.

[0173] The determination method is as follows:

[0174] (1) Pharmaceutical preparation

[0175] One mass of the active compound of formula (I) was dissolved in a mixture of acetone and dimethyl sulfoxide in a mass ratio of 70:1.5, and then 0.5 times the mass of Tween 80 was added to prepare a solution containing the active compound. The solution containing the active compound was diluted with water to the desired concentration.

[0176] (2) Activity assay of two-spotted spider mites

[0177] Two-spotted spider mites were collected from fields in Baoding City, Hebei Province, and brought back indoors to be raised in an artificial climate chamber using round bean leaves. The temperature was set at (28.0±1.0℃) and the relative humidity at (80.0±5%).

[0178] Adults of the same instar were selected for the toxicity determination of the acaricide. Spider mites were transferred to round bean leaves of the same size using a paintbrush and floated in a petri dish (diameter = 6 cm) filled with water to allow them to escape. Ten female adult twoleaf spider mites were inoculated onto each leaf, with four replicates. The treatment group used 1 mL of diluted acaricide solution, which was evenly sprayed onto the leaf surface using a Potter sprayer. The control group used 1 mL of a solvent without the active compound of formula (I) of this invention, which was evenly sprayed onto the spider mites and leaves using a Potter sprayer. After spraying, the leaves were returned to an artificial climate chamber for observation. Efficacy data were collected after 7 days to determine the activity as a percentage (%). 100% indicates that all mites were killed; 0% indicates that no mites were killed.

[0179] Mortality rate (%) = (Number of dead insects / Number of insects tested) × 100 (%)

[0180] The results showed that treatment with the compounds of the present invention resulted in a mortality rate of at least 90%.

[0181] The partial test results for the two-spotted spider mite are as follows:

[0182] At a dose of 1 ppm, 7 days after administration, compounds I-1 to I-28, I-35 to I-75, I-88, I-98 to I-130, and I-133 to I-174 showed a mortality rate of over 90% against the two-spotted spider mite.

[0183] At a dose of 0.05 ppm, compounds I-1 to I-10 showed a mortality rate of over 90% against the two-spotted spider mite 7 days after administration.

[0184] (3) Activity assay of Southern root-knot nematodes

[0185] Place sand, an active compound solution, a suspension of southern root-knot nematode eggs / larvae, and lettuce seeds in a container. Allow the lettuce seeds to germinate and develop. Galls form on the roots.

[0186] After 14 days, the nematicidal efficacy was determined by the formation of galls, expressed as a percentage. 100% indicates no galls were found; 0% indicates that the number of galls on the treated plants was equivalent to the number of galls on the untreated control group. In this experiment, at a dose of 10 ppm, the compounds of this invention showed efficacy of over 80% against southern root-knot nematodes.

[0187] In this experiment, at a dose of 1 ppm, I-11 to I-17, I-88, and I-152 showed efficacy of over 90% against southern root-knot nematodes.

[0188] At a dose of 0.05 ppm, compounds I-1 to I-10 showed efficacy of over 100% against southern root-knot nematodes.

[0189] (4) Test with small ticks

[0190] Use a pipette to transfer the active compound formulation into a test tube. Transfer 8–10 well-fed female adult cattle ticks (minimum ticks) to another perforated test tube. Immerse the test tube in the active compound formulation, ensuring all ticks are fully moistened. After the liquid is depleted, transfer the ticks to filter paper in a plastic dish and store in a temperature-controlled room.

[0191] Viability was assessed after 7 days by examining the fertilized eggs. Eggs that were not visible to the naked eye from fertilization were stored in a temperature-controlled room until hatching into larvae approximately 42 days later. 100% means no ticks laid any fertilized eggs; 0% means all eggs were fertilized.

[0192] Experimental results:

[0193] At a dose of 10 ppm, 7 days after administration, compounds I-1 to I-17, I-20 to I-80, I-88, I-90 to I-145, I-152, and I-155 to I-170 inhibited the effects on more than 90% of fertilized eggs.

[0194] At a dose of 1 ppm, after 7 days of treatment, I-1 to I-17, I-88, and I-152 showed an inhibitory effect on more than 90% of fertilized eggs.

[0195] At a dose of 0.5 ppm, compounds I-1 to I-9 inhibited the activity of more than 90% of fertilized eggs 7 days after administration.

[0196] 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 combining the various technical features in any other suitable manner and including the order of combination. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A compound represented by formula (I): in: n is selected from 0 or 1; R 1 Selected from halogens, C1-C6 alkyl groups, or C1-C6 alkoxy groups; R 2 R 3 They may be the same or different, and each is independently selected from hydrogen, hydroxyl, nitro, cyano, aldehyde, halogen, C1-C6 alkyl or C1-C6 alkoxy; R 4 R 5 They may be the same or different, and each can be independently selected from hydrogen, C1-C6 alkyl, R 4 R 5 The carbon atoms that can be bonded to them can be linked to form C3-C6 cycloalkyl groups; X and Y can be the same or different, and each can be independently selected from CO or CH2.

2. The compound of formula (I) according to claim 1, characterized in that: n is selected from 0 or 1; R 1 Selected from C1-C4 alkyl, C1-C4 alkoxy, or halogen; R 2 R 3 All are selected from hydrogen; R 4 R 5 They can be the same or different, and each can be independently selected from hydrogen, C1 to C4 alkyl groups, R 4 R 5 The carbon atoms that can be connected to them can form a ring, wherein the ring is a C3-C6 cycloalkyl group; X is selected from CH2; Y is selected from CO.

3. Use of the compound of formula (II) in the preparation of the compound of formula (I) according to any one of claims 1 to 2, wherein R 4 R 5 The definitions of X and X are as defined in claims 1-2.

4. Use of the compound of formula (VII) in the preparation of the compound of formula (I) according to any one of claims 1 to 2, wherein R 1 R 2 R 3 R 4 R 5 The definitions of X and Y are as defined in claims 1-2.

5. A method for preparing the compound of formula (I) according to any one of claims 1 to 2, characterized in that, Including at least one of the following schemes, Option 1: Prepare compound (I) by reacting compound (II) with compound (III) or its ammonium salt, as shown in the following reaction formula: Option 2: The compound of formula (II) reacts with the compound of formula (III) or its ammonium salt to obtain the intermediate of formula (IV), and then the compound of formula (I) is prepared from the intermediate of formula (IV). The reaction formula is as follows: Option 3: Compound (II) is reacted with compound (III) or its ammonium salt via intermediates (IV) and (V) to prepare compound (I), as shown in the following reaction formula: Where, n, R 1 R 2 R 3 R 4 R 5 X is defined as in claims 1 to 2, Y is CO; LG is a leaving group; in formulas (I), (IV) and (V), n = 0 can be converted to n = 1 through an oxidation reaction.

6. The preparation method according to claim 5, characterized in that, LG is one of Cl, Br, OTs, OMs, and OBs.

7. A method for preparing the compound of formula (I) according to any one of claims 1 to 2, characterized in that, Including the following reactions: Where, n, R 1 R 2 R 3 R 4 R 5 The definitions of X and Y are as described in claims 1 to 2.

8. The method for preparing the compound of formula (I) according to claim 7, characterized in that, Formula (VII) can be prepared by one of the following methods: Option 1: Prepare compound (VII) by reacting compound (II) with compound (VI) or its ammonium salt, as shown in the following reaction formula: Option 2: The compound of formula (II) reacts with the compound of formula (VI) or its ammonium salt to obtain the intermediate of formula (VIII), and then the compound of formula (VII) is prepared from the intermediate of formula (VIII). The reaction formula is as follows: Option 3: Compound (II) is reacted with compound (VI) or its ammonium salt via intermediates (VIII) and (IX) to prepare compound (VII), as shown in the following reaction formula: In Schemes 1 to 3, Y=CO can be converted into Y=CH2 through a reduction reaction.

9. An active compound composition comprising at least one compound of general formula (I) as described in any one of claims 1 to 2.

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