Preparation and use of substituted alkyl thioether (sulfoxide) group arylamine derivative

Abstract

The present invention relates to preparation and a use of substituted alkyl thioether (sulfoxide) group arylamine derivative. Specifically, the present invention relates to a compound of formula (I) as a substituted alkyl thioether (sulfoxide) group arylamine derivative or an isotopically labeled compound thereof, or an optical isomer, geometric isomer, tautomer or mixture of isomers thereof, or an agrochemically acceptable salt thereof, and a use of the compound in the preparation of an acaricide for mite pest control. Such a compound can achieve a better mite pest control effect at a lower dose.

Description

Preparation and application of substituted alkyl sulfide (sulfoxide) group arylamine derivative TECHNICAL FIELD

[0001] The present application relates to the technical field of pesticides, in particular, to the preparation and application of substituted alkyl sulfide (sulfoxide) group arylamine derivative. BACKGROUND

[0002] In recent years, due to long-term and large-scale use of insecticides and acaricides, a large number of reports on insecticide and acaricide resistant populations have been reported. The use of existing insecticides and acaricides has failed to achieve effective control of insect pests and acarids and insects. Therefore, it is urgent to develop new insecticide and acaricide active compounds effective against existing insecticide and acaricide resistant populations. With the continuous development and research of researchers, trifluoroethyl-substituted sulfur-containing compounds gradually entered the researchers' field of vision. WO1999055668A, CN103664811A, JP2011042611A, JP2011219419A, JP2015036377A, WO 2012 / 012086848, WO 2013 / 018928 and WO 2019 / 131575, CN118344315A all studied trifluoroethyl-substituted sulfur-containing compounds. But the above research results are still not very satisfactory in efficacy, durability, toxicity, cost, etc.

[0003] It is known that the active compounds described in the above-mentioned documents still have low killing activity when controlling pests, acarids and insects, especially at low use rates, their insecticide and acaricide activity is often unsatisfactory, and the production cost is high, so there is still an urgent need in agricultural production for new drugs with high efficiency, low toxicity and excellent killing effect on resistant mites. SUMMARY

[0004] The purpose of the present application is to provide a new class of substituted alkyl sulfide (sulfoxide) group arylamine derivatives. This class of compounds can achieve better pest control effect at a lower dose, can efficiently kill insects, acarids and insects, and can be used to control animal pests (including arthropods and particularly representatives of the order of insects or acarids). Moreover, the synthesis process of the compound provided by the present application is simple, the production cost is low, and it has great development potential in the future.

[0005] In a first aspect, the present application provides a compound of formula (I) as a substituted alkyl sulfide (sulfoxide) group arylamine derivative, or an isotopically labeled compound thereof, or an optical isomer, a geometric isomer, a tautomer or an isomer mixture thereof, or a pesticidally acceptable salt thereof,

[0006] wherein,

[0007] R1is selected from the group consisting of C1-C3alkyl, C1-C3haloalkyl;

[0008] R2, R4are independently from each other selected from the group consisting of halogen, cyano, C1-C3alkyl, C1-C3haloalkyl, C1-C3cycloalkyl;

[0009] R3is selected from the group consisting of hydrogen; R5is selected from the group consisting of hydrogen;

[0010] R6is selected from the group consisting of hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C6-C 10 heteroaryl, C6-C 10 aryl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C3-C6cycloalkylcarbonyl, C6-C 10 arylcarbonyl, C1-C6alkoxycarbonylC1-C3alkyl, C1-C6alkylthiocarbonylC1-C3alkyl, C1-C6alkylaminocarbonyl, C1-C6dialkylaminocarbonyl, C1-C6alkylsulfoxide, C1-C6alkylsulfone, C1-C6alkyloxalyl;

[0011] Q is selected from the group consisting of

[0012] and can be mono- or poly-substituted with one or more identical or different substituents selected from the group consisting of halogen, C1-C4alkyl, C1-C3haloalkyl, C1-C3alkoxy, C3-C6cycloalkyl, hydroxy, cyano, formyl, nitro, amino, trifluoroethylthio;

[0013] n is selected from 0, 1 or 2.

[0014] In one embodiment of the present application, wherein,

[0015] R1is selected from the group consisting of C1-C3alkyl, C1-C3haloalkyl;

[0016] R2, R4are independently from each other selected from the group consisting of halogen, cyano, C1-C3alkyl, C1-C3haloalkyl, C1-C3cycloalkyl;

[0017] R3is selected from the group consisting of hydrogen; R5is selected from the group consisting of hydrogen;

[0018] R6is selected from the group consisting of hydrogen, C1-C3alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C3alkyl, C6-C 10 heteroaryl, C6-C 10 aryl, C1-C3alkylcarbonyl, C1-C3alkoxycarbonyl, C3-C6cycloalkylcarbonyl, C6-C 10arylcarbonyl, C1-C3alkoxycarbonyl C1-C3alkyl, C1-C3alkylthio C1-C3alkylcarbonyl, C1-C3alkylaminocarbonyl, C1-C3dialkylaminocarbonyl, C1-C3alkylsulfoxyl, C1-C3alkylsulfone, C1-C3alkyloxalyl, or C1-C3alkyloxalyl;

[0019] Q is selected from

[0020] and can be mono- or poly-substituted by one or more identical or different substituents selected from the group consisting of halogen, C1-C4alkyl, C1-C3haloalkyl, C1-C3alkoxy, C3-C6cycloalkyl, hydroxy, cyano, aldehydo, nitro, amino, trifluoromethylthio;

[0021] n is selected from 0, 1 or 2.

[0022] In one embodiment of the present application, wherein,

[0023] R1is selected from methyl, ethyl, propyl, fluoromethyl, difluoromethyl, trifluoromethyl, difluoroethyl (CF2CH3, CH2CHF2, CHFCFH2), trifluoroethyl (CH2CF3, CHFCHF2, CF2CFH2), tetrafluoroethyl (CHFCF3, CF2CHF2), pentafluoroethyl, trifluoropropyl, heptafluoropropyl;

[0024] R2, R4are independently from each other selected from fluorine, chlorine, bromine, iodine, methyl, ethyl, propyl, fluoromethyl, difluoromethyl, trifluoromethyl, trifluoroethyl (CH2CF3, CHFCHF2, CF2CFH2), pentafluoroethyl, trifluoropropyl, heptafluoropropyl, cyano, cyclopropyl;

[0025] R3is selected from hydrogen; R5is selected from hydrogen;

[0026] R6is selected from hydrogen, methyl cyano, C1-C3alkyl, C3-C6cycloalkyl C1-C3alkyl, C1-C3alkylcarbonyl, C1-C3alkoxycarbonyl, C3-C6cycloalkylcarbonyl, C6-C8arylcarbonyl, C1-C3alkylsulfoxyl, C1-C3alkylsulfone, C1-C3alkyloxalyl;

[0027] Q is optionally selected from

[0028] and can be mono- or poly-substituted by one or more identical or different substituents selected from the group consisting of halogen, C1-C4alkyl, C1-C3haloalkyl, C1-C3alkoxy, C3-C6cycloalkyl, hydroxy, cyano, aldehydo, nitro, amino, trifluoromethylthio;

[0029] n is selected from 0, 1 or 2.

[0030] In one embodiment of the present application, wherein,

[0031] R1is selected from CH2CF3, CH2CH2CF3;

[0032] R2, R4are independently of each other selected from hydrogen, fluorine, chlorine, bromine, methyl, cyano;

[0033] R3is selected from hydrogen; R5is selected from hydrogen;

[0034] R6is selected from hydrogen, methyl cyano, methyl, ethyl, propyl, cyclopropylmethyl, cyclobutylmethyl, cyclopropylethyl, cyclobutylethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, phenylcarbonyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, oxalyl;

[0035] Q is optionally selected from

[0036] and can be mono- or poly-substituted with one or more identical or different substituents selected from fluorine, chlorine, methyl, ethyl, propyl, methoxy, trifluoromethyl, trifluoroethyl, tert-butyl, cyclopropyl, hydroxy, cyano, aldehydo, nitro, amino, trifluoroethylthio;

[0037] n is selected from 0, 1 or 2.

[0038] In another embodiment of the present application, wherein,

[0039] R1is selected from CH2CF3, CH2CH2CF3;

[0040] R2is selected from fluorine, chlorine, bromine, methyl, cyano; R3is selected from hydrogen;

[0041] R4is selected from fluorine, chlorine, bromine, methyl, cyano; R5is selected from hydrogen;

[0042] R6is selected from hydrogen, methyl cyano, methyl, ethyl, cyclopropylmethyl, methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, cyclopropylcarbonyl, phenylcarbonyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, oxalyl;

[0043] Q is selected from Q1, and can be mono- or poly-substituted with one or more identical or different substituents selected from fluorine, chlorine, methyl, methoxy, trifluoromethyl, cyclopropyl, hydroxy, cyano, aldehydo, nitro, amino, trifluoroethylthio;

[0044] or Q is optionally selected from Q2, Q3or Q4, and can be mono- or poly-substituted with one or more identical or different substituents selected from fluorine, chlorine, hydroxy, trifluoromethyl, cyano, nitro;

[0045] n is selected from 0, 1 or 2.

[0046] In another embodiment of the present application, wherein,

[0047] R1is selected from CH2CF3, CH2CH2CF3; R2is selected from fluorine, chlorine, methyl; R3is selected from hydrogen; R4is selected from fluorine, chlorine; R5is selected from hydrogen; R6is selected from hydrogen, methyl, methylcarbonyl;

[0048] Q is optionally selected from Q1, Q2, Q3or Q4, and can be mono- or poly-substituted by one or more, identical or different substituents selected from fluorine, chlorine, trifluoromethyl, nitro, cyano;

[0049] n is selected from 0, 1 or 2.

[0050] In particular, in another embodiment of the present application, wherein,

[0051] R1is selected from CH2CF3, CH2CH2CF3; R2is selected from fluorine, chlorine, methyl; R4is selected from fluorine, chlorine, bromine; R6is selected from hydrogen, methyl, methylcarbonyl;

[0052] X1, X2, X3, X4, X5are optionally selected from hydrogen, fluorine, chlorine, trifluoromethyl, cyano, nitro, with the proviso that not all are hydrogen;

[0053] n is selected from 0, 1 or 2.

[0054] Further, in another embodiment of the present application, wherein,

[0055] R2is selected from fluorine, chlorine, methyl; R4is selected from fluorine, chlorine; R6is selected from hydrogen, methyl, methylcarbonyl;

[0056] X3is selected from fluorine, chlorine, trifluoromethyl;

[0057] n is selected from 0, 1 or 2.

[0058] Further, in another embodiment of the present application, wherein,

[0059] R2is selected from fluorine, chlorine, methyl; R4is selected from fluorine, chlorine; R6is selected from hydrogen, methyl, methylcarbonyl;

[0060] X2, X3are optionally selected from fluorine, chlorine, cyano, trifluoromethyl;

[0061] n is selected from 0, 1 or 2.

[0062] Further, in another embodiment of the present application, wherein,

[0063] R2is selected from fluoro, chloro, methyl; R4is selected from fluoro, chloro, bromo, methyl; R6is selected from hydrogen, methyl, methylcarbonyl;

[0064] X2, X3, X4are independently selected from fluoro, chloro, cyano, trifluoromethyl;

[0065] n is selected from 0, 1 or 2.

[0066] Further, in another embodiment of the present application, wherein,

[0067] R2is selected from fluoro, chloro, methyl; R4is selected from fluoro, chloro, bromo, methyl; R6is selected from hydrogen, methyl, methylcarbonyl;

[0068] X2, X3, X4, X5are independently selected from fluoro, chloro, cyano, trifluoromethyl;

[0069] n is selected from 0, 1 or 2.

[0070] In particular, in another embodiment of the present application, wherein,

[0071] R1is selected from CH2CF3; R2is selected from methyl; R4is selected from fluoro;

[0072] R6is selected from hydrogen, methyl, acetyl;

[0073] X2, X4are selected from hydrogen; X3, X5are independently selected from hydrogen, fluoro, chloro, trifluoromethyl, with the proviso that not all are hydrogen;

[0074] n is selected from 0, 1 or 2.

[0075] In particular, in another embodiment of the present application, wherein,

[0076] R1is selected from CH2CF3; R2is selected from methyl; R4is selected from fluoro;

[0077] R6is selected from hydrogen, methyl, acetyl;

[0078] X3, X4, X5are independently selected from hydrogen, fluoro, chloro, trifluoromethyl, with the proviso that not all are hydrogen;

[0079] n is selected from 0, 1 or 2.

[0080] In particular, in another embodiment of the present application, wherein,

[0081] R1is selected from CH2CF3; R2is selected from methyl; R4is selected from fluoro;

[0082] R6is selected from hydrogen, methyl;

[0083] X2, X4, X5 are independently selected from hydrogen, fluorine, chlorine, trifluoromethyl, with the proviso that not all are hydrogen;

[0084] n is selected from 0, 1 or 2.

[0085] For the sake of brevity, the term "substituted alkylthio (sulfoxide) group arylamine derivative", "compound of formula (I)" or "compound of the present invention" hereinafter can also encompass any isotopically-labelled compound of formula (I), or an optical isomer, a geometric isomer, a tautomer or an isomer mixture thereof, or a pesticidally acceptable salt thereof.

[0086] The term "optical isomer" means that, when a compound has one or more chiral centers, each chiral center can exist in either the R or S configuration, the various isomers resulting therefrom being optical isomers. Optical isomers include all diastereomeric, enantiomeric, meso forms or mixtures thereof. Optical isomers can be separated for example by chiral chromatography or by chiral synthesis.

[0087] The term "geometric isomer" means that, when a compound has a double bond, the compound can exist as a cis isomer, a trans isomer, an E isomer and a Z isomer. Geometric isomers include cis isomers, trans isomers, E isomers, Z isomers or mixtures thereof.

[0088] The term "tautomer" means isomers that differ in the position of a proton. It is understood by the skilled person that tautomers can be converted into each other and can coexist in a state of equilibrium.

[0089] The term "nematodes" includes all species of the phylum Nematoda and in context especially species that are parasitic on plants (e.g. species of Aphelenchida, Meloidogae, Tylenchida and others).

[0090] Unless otherwise specified, the term "substituted alkylthio (sulfoxide) group arylamine derivative", "compound of formula (I)" or "compound of the present invention" as mentioned herein encompasses also isotopically-labelled compounds, wherein one or more atoms are replaced by atoms having the same atomic number but different atomic mass or mass number as found in nature. The present invention includes all pharmaceutically acceptable isotopically-labelled compounds of formula (I) wherein one or more atoms are replaced by atoms having the same atomic number but different atomic mass or mass number as found in nature.

[0091] Examples of isotopes suitable for inclusion in the compounds of the present invention include isotopes of hydrogen, such as 2H(D) and 3 H(T), isotopes of carbon, such as 11 C, 13 C and 14 C, isotopes of chlorine, such as 37 Cl, isotopes of fluorine, such as 18 F, isotopes of iodine, such as 123 I and 125 I, isotopes of nitrogen, such as 13 N and 15 N, isotopes of oxygen, such as 15 O, 17 O and 18 O, and isotopes of sulfur, such as 35 S.

[0092] Isotopically-labeled compounds of formula (I) can generally be prepared by conventional techniques known to those skilled in the art or by the replacement of prior art non- isotopic markers with isotopic ones. Methods for their production are described, for example, in the examples and preparations appended hereto.

[0093] The compounds of formula (I) can exist in the form of a salt which is acceptable in the art of agrochemicals, such as, for example, acid addition salts and / or base addition salts of the compounds of formula (I). As used herein, "salt acceptable in the art of agrochemicals" includes acid addition salts or base addition salts which can occur in the compounds of formula (I), unless otherwise indicated.

[0094] The salts acceptable in the art of agrochemicals of the compounds of formula (I) include acid addition salts and base addition salts thereof. Suitable acid addition salts are formed from acids which form nontoxic salts. For a review on suitable salts see Handbook of Pharmaceutical Salts: Properties, Selection and Use by Stahl and Wermuth (Wiley-VCH, 2002). Methods for making the salts acceptable in the art of agrochemicals of the compounds described herein are known to those skilled in the art.

[0095] To avoid ambiguity, the following definitions of the terms used herein are provided. The terms used herein have the following meanings, unless specified otherwise.

[0096] As used herein, the term "substituted" means that one or more (preferably 1 to 5, more preferably 1 to 3) hydrogen atoms in a group are independently replaced with the corresponding number of substituents.

[0097] As used herein, the term "each independently" means that when the number of substituents is more than one, these substituents can be the same or different.

[0098] As used herein, the term "alkyl" refers to saturated aliphatic hydrocarbons, including straight-chain and branched-chain. In some embodiments, alkyl groups have 1-8, or 1-6, or 1-3 carbon atoms. For example, the term "C 1-8 As used herein, the term "alkyl" refers to saturated aliphatic hydrocarbons, including straight-chain and branched-chain. In some embodiments, alkyl groups have 1-8, or 1-6, or 1-3 carbon atoms. For example, the term "C 1-8 As used herein, the term "alkyl" refers to saturated aliphatic hydrocarbons, including straight-chain and branched-chain. In some embodiments, alkyl groups have 1-8, or 1-6, or 1-3 carbon atoms. For example, the term "C 1-6 As used herein, the term "alkyl" refers to saturated aliphatic hydrocarbons, including straight-chain and branched-chain. In some embodiments, alkyl groups have 1-8, or 1-6, or 1-3 carbon atoms. For example, the term "C Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, 2-pentyl, 3-pentyl, isopentyl, neopentyl, (R)-2-methylbutyl, (S)-2-methylbutyl, 3-methylbutyl, 2,3-dimethylpropyl, 2,3-dimethylbutyl, hexyl, and the like. Alkyl groups can optionally be substituted with one or more (e.g., 1 to 5) suitable substituents.

[0099] As used herein, the term "haloalkyl" refers to an alkyl group having one or more halogen substituents (up to perhaloalkyl, i.e., each hydrogen atom of the alkyl group is replaced with a halogen atom). For example, the term "C 1- As used herein, the term "haloalkyl" refers to an alkyl group having one or more halogen substituents (up to perhaloalkyl, i.e., each hydrogen atom of the alkyl group is replaced with a halogen atom). For example, the term "C 1- As used herein, the term "haloalkyl" refers to an alkyl group having one or more halogen substituents (up to perhaloalkyl, i.e., each hydrogen atom of the alkyl group is replaced with a halogen atom). For example, the term "C 1- As used herein, the term "haloalkyl" refers to an alkyl group having one or more halogen substituents (up to perhaloalkyl, i.e., each hydrogen atom of the alkyl group is replaced with a halogen atom). For example, the term "C 1- As used herein, the term "haloalkyl" refers to an alkyl group having one or more halogen substituents (up to perhaloalkyl, i.e., each hydrogen atom of the alkyl group is replaced with a halogen atom). For example, the term "C Examples of haloalkyl groups include: CF3, C2F5, CHF2, CH2F, CH2CF3, CH2Cl, and the like. In the case of polyhalo, the halogen atoms can be the same or different. In the context of the present application, the halogen is fluorine, chlorine, bromine, or iodine, especially fluorine, chlorine, or bromine.

[0100] As used herein, the term "alkoxy" refers to O-alkyl, either by itself or in combination with other terms, e.g., haloalkoxy, and is understood in the present application to mean O-alkyl, wherein the term "alkyl" is as defined above.

[0101] As used herein, the term "cycloalkyl" refers to C3-C8-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Among these groups, C3-C6-cycloalkyl is preferred.

[0102] As used herein, the term "n-membered heterocycloalkyl" refers to a heterocycloalkyl group having m ring-forming carbon atoms and (n-m) ring-forming heteroatoms selected from O, S and N. For example, 4-6 membered heterocycloalkyl includes, but is not limited to, oxetane, thietane, azetidine, tetrahydrofuran, tetrahydrothiophene, pyrrolidine, tetrahydropyran, tetrahydrothiopyran, piperidine, morpholine, piperazine. Further, the heterocycloalkyl group can be optionally substituted with one or more suitable substituents.

[0103] Herein, the numerical ranges in connection with the number of substituents, the number of carbon atoms, the number of ring atoms are intended to include each and every sub-range of the indicated range. For example, "1-4 substituents" is intended to include 1, 2, 3, or 4 substituents; "3-8 ring atoms" is intended to include 3, 4, 5, 6, 7, or 8 ring atoms. Accordingly, the numerical ranges in connection with the number of substituents, the number of carbon atoms, the number of ring atoms also encompass any sub-range within the indicated ranges and each of the sub-ranges is hereby disclosed.

[0104] The compounds of the present application can be prepared in a variety of ways known to one skilled in the art of organic synthesis. The synthesis of specific compounds of the present application can be adapted by one skilled in the art to prepare other compounds by appropriate modification of the reactants and reaction conditions.

[0105] The following synthetic schemes describe the preparation of the compounds disclosed in the present application. In the schemes, R1, R2, R3, R4, R5, R6and n have the meanings described in the present application.

[0106] Intermediate 1 is reacted with different electrophilic reagents in the presence of a base to obtain intermediate 2. Catalytic substitution of halogenated Q containing different substituents with intermediate 2 in the presence of a base to obtain intermediate 3. Intermediate 3 is reacted with different nucleophilic reagents to obtain the target product 4. Intermediate 3 or target product 4 is oxidized in the presence of an oxidizing agent such as hydrogen peroxide to obtain the target product of formula I.

[0107] In addition, the above-mentioned intermediate compounds and their raw materials can be prepared by the methods reported in WO2006043635A1, WO2010100189, CN102341376A, WO2013092350, WO2013157229, WO2007131680, WO2013030262, WO2018015852, WO2014202510, WO2014202505, WO2015004028, WO2021056922 or WO2021005081, etc.

[0108] The present application lists a plurality of synthesized exemplary compounds, the specific selection of groups is shown in the following table, and the compound data is shown in Table 5. It should be understood that the scope of the present application is not limited to the exemplary compounds listed in the following table, and the selection of groups of the compounds in Table 1 below can be combined in any combination without particular limitation. The compounds of the present application are shown below, but the present application is by no means limited to these compounds.

[0109] Table 1 R3, R5 = H, n = 0, specific substituents are shown in the following table

[0110] Table 2 R3, R5 = H, n = 0, specific substituents are shown in the following table

[0111] Table 3 R3, R5 = H, n = 0, specific substituents are shown in the following table

[0112] Table 4 R3, R5 = H, n = 0, specific substituents are shown in the following table

[0113] In general formula I-1, when n = 1, the other substituents correspond to I-001 ~ I-230 of Table 1 in turn, and the representative compound numbers are II-001 ~ II-230; the other substituents correspond to I-401 ~ I-486 of Table 1 in turn, and the representative compound numbers are II-401 ~ II-486. In general formula I-1, when n = 2, the other substituents correspond to I-001 ~ I-230 of Table 1 in turn, and the representative compound numbers are II-001 ~ II-230; the other substituents correspond to I-401 ~ I-486 of Table 1 in turn, and the representative compound numbers are II-401 ~ II-486.

[0114] In general formula I-2-1, when n = 1, the other substituents correspond to I-231 ~ I-293 of Table 2 in turn, and the representative compound numbers are II-231 ~ II-293. In general formula I-2-1, when n = 2, the other substituents correspond to I-231 ~ I-293 of Table 2 in turn, and the representative compound numbers are II-231 ~ II-293.

[0115] In general formula I-2-2, when n = 1, the other substituents correspond to I-294~I-312 of Table 3 in turn, and the representative compounds are numbered as II-294~II-312; the other substituents correspond to I-487~I-504 of Table 3 in turn, and the representative compounds are numbered as II-487~II-504. In general formula I-2-2, when n = 2, the other substituents correspond to I-294~I-312 of Table 3 in turn, and the representative compounds are numbered as II-294~II-312; the other substituents correspond to I-487~I-504 of Table 3 in turn, and the representative compounds are numbered as II-487~II-504.

[0116] In general formula I-2-3, when n = 1, the other substituents correspond to I-313~I-322 of Table 4 in turn, and the representative compounds are numbered as II-313~II-322. In general formula I-2-3, when n = 2, the other substituents correspond to I-313~I-322 of Table 4 in turn, and the representative compounds are numbered as III-313~III-322.

[0117] Table 5 Partial Exemplary Compound Characterization Data

[0118] In a second aspect, the present application provides an insecticide / acaricide composition comprising a compound of formula (I) or an isotopically-labeled compound thereof, or an optical isomer, a geometric isomer, a tautomer, or an isomer mixture thereof, or a pesticidally acceptable salt thereof, and a pesticidally acceptable carrier. The composition can be applied to an animal pest / acarid and / or its habitat to control unwanted animal pests / acarids.

[0119] The formulations comprise at least one compound of the present application and at least one agriculturally useful adjuvant, such as carriers and / or surface-active agents.

[0120] The pesticidally acceptable carrier can be an organic or inorganic inert carrier material, for example, suitable carriers include water, gelatin, gum arabic, magnesium stearate, talc, vegetable oils, polyalkylene glycols, petrolatum, mannitol, cellulose, cellulose derivatives, sodium saccharin, magnesium carbonate, saline, glycerol, ethanol, and the like. In addition, the insecticide / acaricide composition can also contain other additives, such as preservatives, stabilizers, emulsifiers, buffers, diluents, binders, wetting agents, lubricants, flow agents, and the like.

[0121] The compounds of formula (I) according to the present application can also be used as a mixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbials, beneficial microorganisms, herbicides, fertilizers, bird repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators, for example to broaden the spectrum of action, to prolong the duration of action, to increase the rate of action, to prevent repellence or to prevent the development of resistance. Furthermore, such active ingredient combinations can improve plant growth and / or tolerance to abiotic factors, for example to high or low temperatures, to drought or to high water content or soil salinity. Flowering and fruit set performance, germination capacity and root development can also be improved, harvest can be facilitated and yield increased, ripening can be influenced, the quality and / or nutritional value of the harvested products can be increased, the shelf life of the harvested products can be prolonged and / or the processing properties of the harvested products can be improved.

[0122] The dosage form of the insecticide / acaricide composition according to the present application can be a liquid dosage form, a solid dosage form or a semi-solid dosage form, without particular limitation. In some embodiments, the dosage form of the insecticide composition is selected from the group consisting of a powder, a granule, a liquid, a suspension or a spray, preferably a wettable powder, a wettable liquid, a soluble powder, a dispersible liquid, an aqueous agent, a microemulsion, an emulsion oil, an aqueous emulsion, a sprayable solution, a dispersible oil suspension, a microcapsule suspension, a water dispersible granule, a water soluble granule, a large granule, a granule for broadcasting and soil application, an aerosol, an ultra-low volume agent and a wax preparation.

[0123] The content of the compound according to the present application in its insecticide / acaricide composition can be adjusted according to the actual needs (e.g. dosage form, mode of application, application object, etc.), including but not limited to 0.001 mg / L-10 mg / L, for example 0.001 mg / L, 0.01 mg / L, 0.1 mg / L, 0.5 mg / L, 1 mg / L, 2.5 mg / L, 5 mg / L or 10 mg / L.

[0124] The specific frequency of application can be determined by a person skilled in the relevant art, for example 1 time per day, 1 time per 2 days, 1 time per 3 days, 1 time per 4 days, 1 time per 5 days, 1 time per 6 days, 2 times per day, 3 times per day, etc.

[0125] In a third aspect, the present application provides the use of a compound of formula (I) or an isotopically-labeled compound thereof, or an optical isomer, a geometric isomer, a tautomer or a mixture of isomers thereof, or a pesticidally acceptable salt thereof, for the preparation of an insecticide / acaricide for the control of pests / acarids.

[0126] The compounds of the present application are suitable for controlling pests or insect pests, i.e. for controlling harmful or unwanted insects or acarids, especially in the agricultural, in the forestry, in the protection of stored goods and in the protection of materials and in the hygiene sector, and exhibit excellent control of a wide variety of pests or insect pests at low rates of application and are active at all stages of development, i.e. eggs, larvae (nymphs), pupae, and adults, and also exhibit excellent control of pests which are resistant to conventional insecticides or acaricides.

[0127] The present application also relates to a method for controlling pests or insect pests, which comprises applying to the locus, the habitat of the insects, the habitat of the pests, the area to be protected, or directly on the insects to be controlled a controlling effective amount of a compound of formula (I). The compounds of the present application can also be used for controlling other invertebrate pests or organisms.

[0128] In particular, the habitat of the insects, the habitat of the pests or the habitat of the acarids is the environment in which the insects, the pests or the acarids live or in which their eggs are present, including the surrounding air, the food to be consumed or the object to be touched. For example, by applying the active compounds to the seeds of the plants (before planting), to the seedlings, or to the planted cuttings, leaves, stems, fruits, grains and / or roots, or to the soil or other growth medium (before or after planting of the crop), it is possible to control insects or acarids which consume, destroy or touch the edible agricultural products, ornamental plants, turf, pasture plants or other plants of economic value, and it is also possible to control sap-sucking pests such as whiteflies, plant hoppers, aphids and the like or acarids such as two-spotted spider mites, carmine spider mites and the like in order to protect these plants against diseases caused by viruses, fungi or bacteria; the plants include plants which are propagated by conventional methods and also plants which have been modified by modern biotechnology to be insect- or acarid-resistant, herbicide-resistant, high-yielding and / or otherwise have advantageous properties. It can be expected that the compounds will be suitable for protecting fabrics, paper, stored grains, seeds and other foodstuffs, houses, buildings and the like from pests and / or organisms by applying the compounds of the present application to these objects or in the vicinity of these objects, for example directly using conventional treatment methods or by allowing the compounds to act on the environment, habitat or storage space, for example by dipping, spraying, evaporating, atomizing, spreading, painting, injecting, and in the case of propagation material, especially seeds, also by applying one or more coats.

[0129] In the field of animal health, i.e. veterinary medicine, the compounds of formula (I) according to the application have activity against animal parasites, in particular ectoparasites or endoparasites. The term "endoparasites" includes in particular helminths and protozoa, such as coccidia. Ectoparasites are usually and preferably arthropods, in particular insects or mites.

[0130] In the field of veterinary medicine, the compounds of formula (I) having a favourable toxicity to warm-blooded animals are suitable for controlling parasites which occur in the animal breeding and animal keeping of domestic animals, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are active against all or specific developmental stages of the parasites.

[0131] Agricultural domestic animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, water buffalo, rabbits, reindeer, fallow deer, and in particular cattle and swine; or poultry such as turkeys, ducks, geese, and in particular chickens; or, for example, fish or crustaceans in aquaculture; or, as appropriate, insects such as bees.

[0132] Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and in particular dogs, cats, caged birds; reptiles, amphibians or ornamental fish.

[0133] With regard to the field of animal health, the term "control" or "controlling" herein means that the compounds of formula (I) are effective in reducing the incidence of a particular parasite to a non-damaging level in animals infected with such parasites. More specifically, "control" herein means that the compounds of formula (I) kill, inhibit the growth of, or inhibit the reproduction of the respective parasites.

[0134] In the context of the present patent application, the term "hygiene" is to be understood as meaning any and all measures, precautions and methods which are aimed at preventing illnesses, in particular infectious diseases, and which serve to protect the health of humans and animals and / or to protect the environment and / or to maintain cleanliness. In accordance with the present application, this includes in particular measures for cleaning, disinfecting and sterilizing, for example, textiles or hard surfaces, in particular surfaces made of glass, wood, cement, porcelain, ceramic, plastic or metal, in order to protect them from hygienic pests / mite pests and / or their secretions. In this respect, the scope of protection of the present application preferably excludes methods which are applied in surgical or therapeutic treatment of the human or animal body and diagnostic methods which are carried out on the human or animal body.

[0135] The term "hygiene sector" thus encompasses all areas, technical fields and industrial applications in which these hygiene measures, precautions and methods are important, for example hygiene in kitchens, bakeries, airports, bathrooms, swimming pools, department stores, hotels, hospitals, stables, animal keeping, etc.

[0136] The inventors of this invention have discovered that even when applied in low doses, the compounds of this invention are effective in controlling animal pests / mites, particularly insects, arachnids, worms, nematodes, and mollusks, encountered in agriculture, horticulture, livestock farming, aquaculture, forestry, landscaping and recreational facilities, protection of stored products and materials, and sanitation. These compounds are preferably used as insecticides / miticides. They are effective against both commonly susceptible and resistant species, and against all or part of the developmental stages. The aforementioned pests include animal pests, and specifically include insects, mites, or nematodes:

[0137] Pests / mites from the phylum Arthropoda, especially from the class Arachnida, such as those from the order Acarina, including the family Tetranychidae (e.g., *Tetranychus* spp., *Eotetranychus* spp., *Panonychus* spp., or *Oligonychus* spp.), such as those from the genera *Acarus* (e.g., *Acarus siro*, *Aceria kuko*, *Aceriasheldoni*), *Aculops* spp., and *Aculus* spp. (e.g., *Aculus fockeui*, *Aculus*). schlechtendali), Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp. (e.g., Brevipalpus phoenicis), Bryobia graminum (e.g., Bryobalpus praetiosa), Centruroides spp., Chorioptes spp., Dermatophagoides pteronyssinus (e.g., Dermatophagoides farinae), Dermacentor spp., Dermanyssus gallinae;

[0138] Pests / mites from the order Coleoptera, such as the striped leaf beetle (Acalymma vittatum), bean weevil (Acanthoscelides obtectus), beetle (Adoretus spp.), poplar leaf beetle (Agelasticaalni), click beetle (Agriotes spp.) (e.g., straight click beetle (Agriotes linneatus), wireworm (Agriotes mancus)), black fungus beetle (Alphitobius diaperinus), June beetle (Amphimallon solstitialis), furniture thieving beetle (Anobium punctatum), longhorn beetle (Anoplophora spp.), flower weevil (Anthonomus spp.) (e.g., cotton boll weevil (Anthonomus grandis)), round beetle (Anthrenus spp.), pear weevil (Apion spp.), and sugarcane beetle (Apogonia). spp.), genus *Atomaria* (e.g., *Atomaria linearis*), genus *Attagenus*, genus *Baris caerulescens*, genus *Bruchidius obtectus*, genus *Bruchus* (e.g., *Bruchus pisorum*, *Bruchus rufimanus*), genus *Cassida*, genus *Cerotoma trifurcata*, genus *Ceuthorhynchus* (e.g., *Ceutorrhynchus assimilis*, *Ceutorrhynchus quadridens*, *Ceutorrhynchus rapae*), genus *Chaetocnema* (e.g., *Chaetocnema*). Confinis, Chaetocnemadenticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp. (e.g., Cosmopolites sordidus);

[0139] a pest / invertebrate from the order Diptera (Diptera), for example, Aedes spp. (e.g., Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans), Agromyza spp. (e.g., Agromyza frontella, Agromyza parvicornis), Anastrepha spp., Anopheles spp. (e.g., Anopheles quadrimaculatus, Anopheles gambiae), Asphondylia spp., Bactrocera spp. (e.g., Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae), Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomyia spp., Chrysops spp., Chrysozona pluvialis, Cochliomyia spp., Contarinia spp. (e.g., Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora);

[0140] Pests / mites from the order Heteroptera, such as the pumpkin stink bug (Anasa tristis), *Antestiopsis* spp., *Boisea* spp., *Blissus* spp., *Calocoris* spp., *Campylomma livida*, *Cavelerius* spp., *Cimex* spp. (e.g., *Cimex adjunctus*, *Cimex hemipterus*, *Cimexlectularius*, *Cimex pilosellus*), *Collaria* spp., *Creontiades dilutus*, *Dasynus piperis*, *Dichelops furcatus*, and *Diconocoris*. Hewetti, Dysdercus spp., Euschistus spp.;

[0141] pests / spiders from the order Homoptera, for example Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp. (for example Acyrthosiphon pisum), Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp. (for example Amrasca bigutulla, Amrasca devastans), Anuraphis cardui, Aonidiella spp. (for example Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata), Aphanostigma piri, Aphis spp (for example Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii;

[0142] Pests / mites from the order Hymenoptera, such as the genera *Acromyrmex* spp., *Athalia* spp. (e.g., *Athalia rosae*), *Atta* spp., *Diprion* spp. (e.g., *Diprion similis*), *Hoplocampa* spp. (e.g., *Hoplocampa cookei*, *Hoplocampa testudinea*), and *Lasius* spp.;

[0143] Pests / mites from the order Isoptera, such as *Coptotermes spp.*, *Cornitermes cumulans*, *Cryptotermes spp.*, *Incisitermes spp.*, *Microtermesobesi*, *Odontotermes spp.*, and *Reticulitermes spp.* (e.g., *Reticulitermes flavipes*, *Reticulitermes hesperus*));

[0144] pests / mites from the order Lepidoptera, for example, Achroia grisella, Acronicta major, Adoxophyes spp. (for example, Adoxophyes orana), Aedia leucomelas, Agrotis spp. (for example, Agrotis segetum, Agrotis ipsilon), Alabama spp. (for example, Alabama argillacea), Amyelois transitella, Anarsia spp., Anticarsia spp. (for example, Anticarsia gemmatalis), Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp. (for example, Chilo plejadellus, Chilo suppressalis), Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp.;

[0145] pests / pest mites from the order of the Orthoptera or Saltatoria, for example, Acheta domesticus, Dichroplus spp., Gryllotalpa spp. (for example Gryllotalpa gryllotalpa), Hieroglyphus spp., Locusta spp. (for example Locusta migratoria), Melanoplus spp. (for example Melanoplus devastator), Schistocerca gregaria;

[0146] pests / pest mites from the order of the Thysanoptera, for example, Anaphothrips obscurus, Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens, Frankliniella spp. (for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi), Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp. (for example Thrips palmi, Thrips tabaci);

[0147] Plant pests / pest mites from the phylum Nematoda (Nematoda), i.e. plant parasitic nematodes, in particular Aglenchus spp. (e.g. Aglenchus agricola), Anguina spp. (e.g. Anguina tritici), Aphelenchoides spp. (e.g. Aphelenchoides arachidis, Aphelenchoides fragariae), Belonolaimus spp. (e.g. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni), Bursaphelenchus spp. (e.g. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus); Meloidogyne spp. (e.g. Meloidogyne arenaria, Meloidogyne chitwoodi, Meloidogyne hapla, Meloidogyne incognita); Pratylenchus spp. (e.g. Pratylenchus alleni, Pratylenchus curvitatus, Pratylenchus goodeyi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus scriputeri, Pratylenchus vulnus); Radopholus spp. (e.g. Radopholus similis, Radopholus solani); Tylenchulus spp. (e.g. Tylenchulus semipenetrans); and Xiphinema spp. (e.g. Xiphinema index).(e.g., Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne artiella, Meloidogyne chitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, Meloidogyne exigua, Meloidogyne fallax, Meloidogyne graminicola, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis, Meloidogyne minor, Meloidogyne naasi, Meloidogyne paranaensis, Meloidogyne thamesi, and Meloidogyne spp. that are non-migratory parasites; Tylenchulus spp. (e.g., Tylenchulus semipenetrans), Xiphinema spp. (e.g., Xiphinema index).

[0148] Arthropods from the order of the Phthiraptera, for example Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Ptirus pubis, Trichodectes spp.;

[0149] Arthropods from the order of the Siphonapterida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp., and from the order of the Blattaria the unwanted pests and hygiene pests.

[0150] Depending on the concentration or rate of application, the compounds of the formula (I) can also be used as herbicides, safeners, growth regulators or plant properties improving compositions, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (Mycoplasma-like organisms) and RLO (Rickettsia-like organisms). Depending on the case, they can also be used as intermediates or precursors for the synthesis of further active ingredients.

[0151] The person skilled in the art will understand that the definitions and preferences described in one aspect of the application apply equally to the other aspects. The person skilled in the art will understand that the embodiments of the individual aspects of the application can be combined in various ways without deviating from the subject matter and idea of the application, and that these combinations are also included in the scope of the application.

[0152] The advantageous effects of the present application are:

[0153] A series of novel compounds were designed and synthesized by active substructure splicing, intermediate derivation, and electronic isosterism. Some of the compounds showed excellent acaricidal activity against spider mites at low concentrations, which was better than the mainstream commercial acaricides Spiromesifen. The novel compounds can be used for the control of agricultural or forestry pests and spider mites, especially showing excellent control effect on T. urticae, T. pacificus, A. schlechtendali, and P. citri at low concentrations. At the same time, the synthesis process is simple, the production cost is low, and the potential is huge. DETAILED DESCRIPTION

[0154] The technical solutions in the embodiments of the present application will be clearly and completely described below in combination with the embodiments of the present application. Based on the embodiments in the present application, all other embodiments obtained by those of ordinary skill in the art without creative effort belong to the scope of protection of the present application.

[0155] The compound of formula (I) can be synthesized by various methods familiar to those skilled in the art of organic synthesis. Some exemplary methods for synthesizing the compound of formula (I) are given in the following specific examples, which are well known in the art of synthetic chemistry. Obviously, referring to the exemplary schemes in the present patent, those skilled in the art can easily design the synthesis routes of other compounds of formula (I) by appropriately adjusting the reactants, reaction conditions and protecting groups.

[0156] Example 1 Synthesis of 2-fluoro-N-(2-fluoro-5-(trifluoromethyl)phenyl)-4-methyl-5-((2,2,2-trifluoroethyl)thio)aniline (Compound I-069)

[0157] Into a reaction flask was added a solution of 4-methyl-2-fluoro-5-(2,2,2- trifluoroethylthio)aniline (500 mg, 2.09 mmol) in toluene, after stirring uniformly, then BINAP (52 mg, 0.0418 mmol), Pd(OAc)2(10 mg, 0.0418 mmol), K2CO3(433 mg, 2.51 mmol) were added into the reaction system respectively, and then 3-chloro-4-fluorobenzotrifluoride (560 mg, 2.09 mmol) was added, and the reaction system was heated to 110°C for reaction, and the reaction was tracked by TLC, and it was found that the raw material was completely converted after 16 h at the temperature, the reaction was stopped, and the reaction system was restored to room temperature, saturated brine was added into the reaction system, extracted with ethyl acetate (3 x 15 mL), the organic phase was collected and dried with anhydrous sodium sulfate, the organic phase was concentrated, and column chromatography was used for separation to obtain a total of 0.5 g of compound I-069, and the yield was 59.61%.

[0158] 1 H NMR (400 MHz, CDCl3-d) δ 7.54 (d, J = 8.0 Hz, 1H), 7.40 (dd, J = 7.6, 2.0 Hz, 1H), 7.32 - 7.18 (m, 2H), 7.08 (d, J = 11.2 Hz, 1H), 5.87 (s, 1H), 3.34 (q, J = 9.6 Hz, 2H), 2.50 (s, 3H).

[0159] 13C NMR (100 MHz, CDC13-d) δ 154.4 (d, J = 245.4 Hz), 154.2 (d, J = 246.5 Hz), 136.9 (d, J = 7.3 Hz), 132.0 (d, J = 11.8 Hz), 128.2 (d, J = 3.6 Hz), 127.1 (d, J = 12.2 Hz), 126.2, 125.3 (q, J = 276.7 Hz), 123.7 (q, J = 272.2 Hz), 118.0 (d, J = 20.0 Hz), 117.8 (q, J = 4.1 Hz), 115.9 (d, J = 20.4 Hz), 114.6, 113.0 (m), 37.9 (q, J = 32.9 Hz), 20.2.

[0160] Example 2 Synthesis of 2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)-N-(3,4,5- trifluorophenyl)aniline (Compound 1-117)

[0161] Into a reaction flask was added 4-methyl-2-fluoro-5-(2,2,2-trifluoroethylthio)aniline (500 mg, 2.09 mmol), dissolved in toluene, stirred until homogeneous, then added BINAP (52 mg, 0.0418 mmol), Pd(OAc)2(10 mg, 0.0418 mmol), K2CO3(433 mg, 2.51 mmol), followed by 3,4,5-trifluorobromobenzene (550 mg, 2.09 mmol), heated to 110 °C, and allowed to react at that temperature, TLC tracking of the reaction was performed, when the starting material was completely reacted, saturated brine was added to the reaction system, extracted with ethyl acetate (3 x 15 mL), the organic phase was collected and dried with anhydrous sodium sulfate, the organic phase was concentrated, and column chromatography was used to separate to obtain a total of 0.45 g of compound 1-117, with a yield of 58.30%.

[0162] 1 H NMR (400 MHz, CDC13-d) δ 7.47 (d, J = 8.4 Hz, 1H), 7.04 (d, J = 11.6 Hz, 1H), 6.64-6.56 (m, 2H), 5.62 (s, 1H), 3.32 (q, J = 9.6 Hz, 2H), 2.47 (s, 3H).

[0163] 13C NMR (100 MHz, CDC13-d) δ 154.1 (d, J = 246.4 Hz), 151.3 (ddd, J = 246.3, 10.5, 5.7 Hz), 138.7 (dt, J = 10.8, 3.3 Hz), 136.6 (d, J = 7.4 Hz), 134.6 (dt, J = 243.4, 15.5 Hz), 128.0 (dd, J = 7.9, 4.3 Hz), 125.8, 125.3 (q, J = 276.7 Hz), 117.9 (d, J = 19.8 Hz), 101.2 (d, J = 24.2 Hz), 38.0 (q, J = 32.4 Hz), 20.2.

[0164] Example 3 Synthesis of 3-chloro-N-(2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl)-5- (trifluoromethyl)pyridin-2-amine (Compound 1-268)

[0165] Into a reaction flask was added 4-methyl-2-fluoro-5-(2,2,2-trifluoroethylthio)aniline (500 mg, 2.09 mmol) and then dissolved in toluene. After stirring to homogeneity, BINAP (52 mg, 0.0418 mmol), Pd(OAc)2(10 mg, 0.0418 mmol), K2CO3(433 mg, 2.51 mmol), and then 2,3-dichloro-5-trifluoromethylpyridine (580 mg, 2.09 mmol) were added to the reaction. The reaction was heated to 110 °C and the reaction was followed by TLC. When the starting material was consumed, saturated brine was added to the reaction, extracted with ethyl acetate (3 x 15 mL), the organic phase was collected and dried over anhydrous sodium sulfate, and the organic phase was concentrated. Compound 1-268 was isolated by column chromatography to give a total of 0.62 g with a yield of 70.84%.

[0166] 1 H NMR (400 MHz, CDC13-d) δ 8.70 (d, J = 8.1 Hz, 1H), 8.45 (dd, J = 2.2, 1.1 Hz, 1H), 7.83 (d, J = 2.1 Hz, 1H), 7.41 (d, J = 3.4 Hz, 1H), 7.05 (d, J = 11.5 Hz, 1H), 3.43 (q, J = 9.7 Hz, 2H), 2.48 (s, 3H).

[0167] 13C NMR (100 MHz, CDC13-d) δ 152.9 (d, J = 246.2 Hz), 152.6, 143.4 (q, J = 4.4 Hz), 136.6 (d, J = 7.6 Hz), 133.6 (q, J = 3.4 Hz), 128.2 (d, J = 3.4 Hz), 126.8 (q, J = 275.0 Hz), 126.3, 125.6 (d, J = 10.6 Hz), 125.0 (q, J = 269.6 Hz), 118.7 (q, J = 33.9 Hz), 116.7 (d, J = 20.0 Hz), 116.3, 38.2 (q, J = 32.3 Hz), 20.3.

[0168] Example 4 Synthesis of 3-chloro-N-(2-fluoro-4-methyl-5-(2,2,2-trifluoroethyl)thio)phenyl)-N-methyl-5-(trifluoromethyl)pyridine (Compound 1-275)

[0169] Compound 1-268 (0.5 g, 1.19 mmol) was taken in 10 ml of methanol solution, then TFA (411 mg, 3.60 mmol) was added to the reaction system, stirred for 5 min, and 35% aqueous formaldehyde solution (0.31 g, 3.58 mmol) and NaBH4(76 mg, 11.9 mmol) were added, and the reaction was stirred at 45 °C, TLC monitoring, after the raw material was completely reacted, concentrated under reduced pressure, water was added to the residue, then extracted with DCM (3 x 15 mL), the organic phase was collected and dried with anhydrous sodium sulfate, the organic phase was concentrated, and column chromatography was separated to obtain compound 1-275, a total of 0.32 g, the yield was 61.93%.

[0170] 1 H NMR (400 MHz, CDC13-d) δ 8.54 (s, 1H), 7.78 (s, 1H), 7.46 (d, J = 8.0 Hz, 1H), 7.02 (d, J = 11.4 Hz, 1H), 3.43 (s, 3H), 3.31 (q, J = 9.6 Hz, 2H), 2.50 (s, 3H).

[0171] 13C NMR (100 MHz, CDC13-d) δ 157.2 (d, J = 250.3 Hz), 156.4, 143.1 (q, J = 4.3 Hz), 140.9 (d, J = 8.0 Hz), 138.7 (q, J = 3.6 Hz), 133.0, 130.4 (d, J = 11.5 Hz), 128.3 (d, J = 3.5 Hz), 125.3 (q, J = 275.1 Hz), 123.0 (q, J = 270.1 Hz), 121.4 (q, J = 33.5 Hz), 120.4, 118.1 (d, J = 20.5 Hz), 83.1, 38.0 (q, J = 32.6 Hz), 20.4.

[0172] Example 5 Synthesis of 2-fluoro-N-(2-fluoro-5-(trifluoromethyl)phenyl)-4-methyl-5- ((2,2,2-trifluoroethyl)sulfinyl)aniline (Compound II-069)

[0173] To a round bottom flask was added 2-fluoro-N-(2-fluoro-5-(trifluoromethyl)phenyl)-4- methyl-5-((2,2,2-trifluoroethyl)sulfanyl)aniline (Compound 2) (0.5 g, 1.25 mmol) and 20 mL of DCM solution, under ice bath, to the reaction system was added dropwise 85% m-CPBA (0.31 g, 1.50 mmol) in DCM solution slowly, keeping 0 °C, reaction TLC tracking reaction, after the raw material was completely converted, to the reaction system was added 30% Na2S2O3 aqueous solution, stirred at room temperature for 10 min, then to the reaction system was added saturated NaHCO3 solution, stirred for 10 min, stopped the reaction, the reaction system was extracted with DCM (3 x 15 mL), the organic phase was collected and dried over anhydrous sodium sulfate, filtered, the filtrate was collected and concentrated under reduced pressure, the sample was mixed with silica gel, then column chromatography was used to separate to obtain Compound II-069, a total of 0.43 g, the yield was 85%.

[0174] 1 H NMR (400 MHz, CDC13-d) δ 7.53 (d, J = 8.2 Hz, 1H), 7.40 (d, J = 7.7 Hz, 1H), 7.25 - 7.15 (m, 2H), 7.08 (d, J = 11.3 Hz, 1H), 5.87 (s, 1H), 3.34 (q, J = 9.6 Hz, 2H), 2.49 (s, 3H).

[0175] 13C NMR (100 MHz, CDCI3-d) δ 154.3 (dd, J = 247.5 Hz, 20.0 Hz), 136.9 (d, J = 7.3 Hz), 131.9 (d, J = 11.9 Hz), 129.4, 128.3 - 126.9 (m), 126.6, 126.1, 125.0 (q, J = 247.5 Hz), 123.9 (q J = 247.5 Hz), 122.3, 118.6 - 117.3 (m), 115.8 (d, J = 20.4 Hz), 112.8 (d, J = 4.1 Hz), 37.9 (q, J = 32.9 Hz), 20.1.

[0176] In analogy to the examples and in accordance with the above described methods of preparation, the remaining analogous compounds of formula (I) can be obtained.

[0177] Test Example: Bioactivity test

[0178] Test Example 1 : Bioactivity test against Tetranychus cinnabarinus adults

[0179] Test method: The test was carried out according to the agricultural industry standard NYT 1154.6-2006 using the immersion method. Vicia faba seedlings with uniform growth were selected, the thick and tender leaves were cut into two leaves and one stem, one leaf was then cut from the two leaves and one stem, and inserted into a 5 mL sample bottle filled with water, 30 adult mites were selected for each leaf. Each test agent was accurately weighed, dissolved in a small amount of DMSO, and prepared into a 10000 mg / L stock solution. The stock solution was diluted 100 times with 0.1 % Tween 80 aqueous solution to obtain a test solution with a concentration of 100 mg / L. After the test insects were stable on the leaves, they were immersed in the prepared test solution for 5-10 s, the excess test solution was absorbed with filter paper and naturally dried, each treatment was repeated 3 times, and a blank control was set up, the immersion solution used for the control group was the same proportion of DMSO and Tween aqueous solution. Subsequently, the experimental target was placed in an artificial climate chamber (24-26°C, L:D = 16:8, RH 60%) for cultivation, and after 72 h the mortality of adult mites was checked and recorded. The mites were considered dead if they did not move or react when touched with tweezers.

[0180] Calculation method:

[0181] Corrected mortality (%) = [(treated mortality - control mortality) / (1 - control mortality)] x 100%

[0182] Among the part of the exemplary compounds of the present application, the following compounds have better control effect on T. cinnabarinus adult at a concentration of 100 mg / L, and the mortality rate reaches 100%: compounds I-005, I-007, I-010, I-015, I-023, I-025, I-027, I-037, I-040, I-048, I-052, I-056, I-074, I-076, I-080, I-089, I-101, I-113, I-117, I-118, I-122, I-127, I-128, I-136, I-142, I-144, I-158, I-186, I-176, I-196, I-198, I-200, I-210, I-219, I-231, I-238, I-245, I-261, I-268, I-275, I-292, I-296, I-313, I-401, I-411, I-425, I-430, I-434, I-439, I-487, II-027, II-069, II-117.

[0183] Among the part of the exemplary compounds of the present application, the following compounds have better control effect on T. cinnabarinus adult at a concentration of 1.56 mg / L, and the mortality rate is >90%: compounds I-117, I-118, I-122, I-127, I-136, I-219, I-296, I-425, II-117.

[0184] According to the above method, the compounds 711 (CK1) and 725 (CK2) in the patent CN111825585A were selected to perform the biological activity determination on T. cinnabarinus adult, and the results are shown in Table 6.

[0185] Table 6 Mite-killing activity of part of exemplary compounds on T. cinnabarinus adult

[0186] It can be known from the comparison of the exemplary compounds of the present application with the control compounds CK1, CK2 and the commercial reagent Spirodiclofen that the compounds of the present application have higher mite-killing activity compared with the prior art.

[0187] Test Example 2: Biological activity test on Tetranychus urticae adult

[0188] The test was carried out according to the agricultural industry standard NY / T 1154.13-2008 by using the leaf disc spray method. The kidney bean leaves with clean and flat surface, proper size and uniform leaf age were selected, and then were laid on the Petri dishes with clean filter paper, with the reverse side upward. The filter paper was moisturized by adding water, and then 30-40 female adult T. urticae mites with basically consistent physiological state were introduced to each leaf by using a brush. The compound (20 mg) was dissolved in 2 mL of DMSO solvent to form a primary stock solution with a concentration of 10,000 mg / L. The primary stock solution was diluted 100 times with 0.1% Tween-80 aqueous solution to obtain a secondary stock solution with a concentration of 100 mg / L, and the secondary stock solution was diluted 10 times to obtain a test solution with a concentration of 10 mg / L. The test solution with a concentration of 10 mg / L was further diluted 4 times to obtain test solutions with a concentration of 2.5 mg / L and 0.625 mg / L. The leaf with the female adult T. urticae mites was quantitatively sprayed with 2 mL of the test solution by using a throat sprayer. Each treatment was repeated 3 times, and a blank control group was set. The spraying liquid used in the blank control group was the same proportion of DMSO and Tween aqueous solution. The sprayed Petri dishes were sufficiently dried and sealed with sealing film. The Petri dishes were placed in an artificial climate chamber (24-26℃, L:D = 16:8, RH 60%) for culture, and the death of the female adult T. urticae mites was checked and recorded after 72 h.

[0189] Calculation method:

[0190] Mortality (%) = [(pre-treatment insect population base - post-treatment live insect number) / pre-treatment insect population base] x 100%

[0191] Corrected mortality (%) = [(treatment group mortality - blank control group mortality) / (1 - blank control group mortality)] x 100%

[0192] Among the part of the exemplary compounds of the present application, the following compounds have better control effect on T. urticae adult at a concentration of 100 mg / L, and the mortality reaches 100%: I-007, I-015, I-023, I-025, I-027, I-037, I-040, I-048, I-052, I-074, I-076, I-080, I-089, I-101, I-113, I-117, I-118, I-122, I-127, I-128, I-136, I-142, I-144, I-158, I-186, I-176, I-196, I-200, I-210, I-219, I-231, I-238, I-245, I-261, I-268, I-275, I-292, I-296, I-313, I-401, I-411, I-425, I-430, I-434, I-439, I-487, II-027, II-069, II-117.

[0193] Among the part of the exemplary compounds of the present application, the following compounds have better control effect on Tetranychus urticae adult at a concentration of 2.5 mg / L, and the mortality rate is >90%: compounds I-117, I-118, I-122, I-127, I-136, I-219, I-296, I-425, II-117.

[0194] Test Example 3: Bioactivity test against Panonychus citri female adult

[0195] The test was carried out by referring to the agricultural industry standard NYT 1154.6-2006, using the immersion method. Clean and flat citrus leaves of appropriate size and uniform leaf age were selected, and were placed in a culture dish with clean filter paper, with the reverse side facing up. The filter paper was moistened with water, and then 30-40 Panonychus citri female adults in a physiological state were introduced into each leaf using a brush. The compound (20 mg) was dissolved in 2 mL of DMSO solvent to form a primary stock solution with a concentration of 10,000 mg / L. The primary stock solution was diluted 10 times with 0.1% Tween-80 aqueous solution to obtain a test solution with a concentration of 100 mg / L, and then diluted 10 times to obtain a test solution with a concentration of 10 mg / L. The test solution with a concentration of 10 mg / L was further diluted 5 times to obtain a test solution with a concentration of 2 mg / L, and the test solution with a concentration of 2 mg / L was further diluted 2 times to obtain a test solution with a concentration of 1 mg / L. After the test insects were stable on the leaves, they were immersed in the prepared test solution for 5-10 s, and the excess test solution was absorbed with filter paper and naturally dried. Each treatment was repeated 3 times, and a blank control group was set up. The immersion solution used in the blank control group was the same proportion of DMSO and Tween aqueous solution. Then, the experimental target was placed in an artificial climate chamber (24-26°C, L:D=16:8, RH 60%) for culture, and the mortality of female adults was checked and recorded after 72 h.

[0196] Calculation method:

[0197] Mortality rate (%) = [(pre-treatment insect population base - post-treatment live insect number) / pre-treatment insect population base] x 100%

[0198] Corrected mortality rate (%) = [(treatment group mortality rate - blank control group mortality rate) / (1 - blank control group mortality rate)] x 100%

[0199] Among the part of the exemplary compounds of the present application, the following compounds have better control effect on citrus red mite adult at the concentration of 100 mg / L, and the mortality rate reaches 100%: I-007, I-010, I-015, I-023, I-025, I-027, I-037, I-040, I-048, I-052, I-056, I-074, I-076, I-080, I-089, I-101, I-113, I-117, I-118, I-122, I-127, I-128, I-136, I-158, I-186, I-176, I-196, I-198, I-200, I-210, I-219, I-231, I-238, I-245, I-261, I-268, I-275, I-292, I-296, I-313, I-401, I-411, I-425, I-430, I-434, I-439, I-487, II-027, II-069, II-117.

[0200] Among the part of the exemplary compounds of the present application, the following compounds have better control effect on citrus red mite adult at the concentration of 2 mg / L, and the mortality rate is >90%: compounds I-117, I-118, I-122, I-127, I-136, I-219, I-296, I-425, II-117.

[0201] The inventors introduce the trifluoromethyl chloropyridine fragment of the acaricide fluazinam into the trifluoroethylsulfanyl aniline structure newly developed by the active substructure splicing principle to obtain compound I-268, and it is found through acaricidal activity determination that the mortality of Tetranychus cinnabarinus is greater than 70% at 1.56 ppm, and the activity is poor after reducing the concentration, and the overall activity is not very excellent, and subsequently, the structure of I-268 is derived and optimized by changing the position and substituent of the nitrogen on the pyridine, but the final bioassay results show that the acaricidal activity of similar compounds is not greatly improved. Subsequently, the pyridine ring is replaced by a benzene ring by the method of electronic isostere to obtain compound I-080, and it is found that the acaricidal activities of the two are equivalent, and therefore a large number of derivation and optimization are carried out on the structure of I-080, and it is found through structure-activity relationship analysis that the acaricidal activity is good when the substituents on the benzene ring are electron-withdrawing substituents such as fluorine, chlorine, cyano and trifluoromethyl. Subsequently, a plurality of compounds containing fluorine, chlorine, cyano and trifluoromethyl are designed, and it is found through biological activity that compound I-117 exhibits excellent acaricidal activity. Since the introduction of fluorine atoms in the compound can enhance the binding affinity with the target protein and improve the activity of the compound, fluorine atoms are further introduced on the basis of compound I-117, and finally the compound I-219 with more excellent activity is found. In summary, the inventors design and synthesize a series of novel compounds through active substructure splicing, intermediate derivation and electronic isostere, and part of the compounds exhibit excellent acaricidal activity to the pest mites at low concentrations, and the activity is better than that of the mainstream commercial agent Spiromesifen, and the compounds are expected to become a new type of acaricide compound. At the same time, the synthesis process is simple, the production cost is low, and the potential is huge.

[0202] The inventors design and synthesize a series of novel compounds through active substructure splicing, intermediate derivation and electronic isostere, and part of the compounds exhibit excellent acaricidal activity to the pest mites at low concentrations, and the activity is better than that of the mainstream commercial agent Spiromesifen. The novel compounds can be used for the control of agricultural or forestry pests and acarid pests, and especially exhibit excellent control effect on Tetranychus urticae Koch, Tetranychus cinnabarinus, Panonychus mori and Panonychus citri.

[0203] In organic molecules, due to the difference in electronegativity, size or spatial configuration of substituents, the transport performance of the whole molecule in the bodies of insects, mites and plants and the difference in receptor binding will be great, and the difference in biological activity will also be great, and the transport performance of the molecule and the suitability of receptor binding are unpredictable, and a large amount of creative labor is needed to obtain them, therefore, the present application has substantial characteristics and significant progress.

[0204] The above merely provides the preferred embodiment of the present application, and is not used to limit the present application. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application should be included in the scope of protection of the present application.

Claims

1. A compound of formula (I) as a derivative of a substituted alkyl sulfide (sulfoxide) aromatic amine, or an isotopically labeled compound thereof, or an optical isomer, geometric isomer, tautomer, or mixture of isomers thereof, or a pesticide-acceptable salt thereof, wherein R1is selected from C1-C3alkyl, C1-C3haloalkyl; R2, R4are independently from each other selected from halogen, cyano, C1-C3alkyl, C1-C3haloalkyl, C1-C3cycloalkyl; R3is selected from hydrogen; R5is selected from hydrogen; R6 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C6-C 10 Heterocyclic group, C6-C 10 Aryl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C3-C6 cycloalkyl carbonyl, C6-C 10 Aryl carbonyl, C1-C6 alkoxy carbonyl, C1-C3 alkyl, C1-C6 alkylthio, C1-C3 alkyl carbonyl, C1-C6 alkylamino carbonyl, C1-C6 dialkylamino carbonyl, C1-C6 alkyl sulfoxide, C1-C6 alkyl sulfone, C1-C6 alkyl oxaloyl, C1-C6 alkoxy oxaloyl; Q is selected from and can be mono- or poly-substituted with one or more identical or different substituents selected from the group consisting of halogen, C1-C4alkyl, C1-C3haloalkyl, C1-C3alkoxy, C3-C6cycloalkyl, hydroxyl, cyano, aldehydo, nitro, amino, thfluoroeththio; n is selected from 0, 1 or 2.

2. The compound of formula (I) according to claim 1, characterized in that, wherein R1is selected from C1-C3alkyl, C1-C3haloalkyl; R2, R4are independently from each other selected from halogen, cyano, C1-C3alkyl, C1-C3haloalkyl, C1-C3cycloalkyl; R3is selected from hydrogen; R5is selected from hydrogen; R6 is selected from hydrogen, C1-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C3 alkyl, C6 ...6-C6 cycloalkyl 10 Heterocyclic group, C6-C 10 Aryl, C1-C3 alkyl carbonyl, C1-C3 alkoxy carbonyl, C3-C6 cycloalkyl carbonyl, C6-C 10 Aryl carbonyl, C1-C3 alkoxy carbonyl, C1-C3 alkyl, C1-C3 alkyl thio, C1-C3 alkyl carbonyl, C1-C3 alkyl amino carbonyl, C1-C3 dialkyl amino carbonyl, C1-C3 alkyl sulfoxide, C1-C3 alkyl sulfone, C1-C3 alkyl oxaloyl or C1-C3 alkoxy oxaloyl; Q is selected from and can be mono- or poly-substituted with one or more identical or different substituents selected from the group consisting of halogen, C1-C4alkyl, C1-C3haloalkyl, C1-C3alkoxy, C3-C6cycloalkyl, hydroxyl, cyano, aldehydo, nitro, amino, thfluoroeththio; n is selected from 0, 1 or 2.

3. The compound of formula (I) according to claim 1, characterized in that wherein R1is selected from C1-C3alkyl, C1-C3haloalkyl; R2, R4are independently from each other selected from halogen, cyano, C1-C3alkyl, C1-C3haloalkyl, C1-C3cycloalkyl; R3is selected from hydrogen; R5is selected from hydrogen; R6is selected from hydrogen, methylcyano, C1-C3alkyl, C3-C6cycloalkyl C1-C3alkyl, C1-C3alkylcarbonyl, C1-C3alkoxycarbonyl, C3-C6cycloalkylcarbonyl, C6-C8arylcarbonyl, C1-C3alkylsulphoxy, C1-C3alkylsulfonyl, C1-C3alkyloxalyl; Q is arbitrarily selected from and can be mono- or poly-substituted with one or more identical or different substituents selected from the group consisting of halogen, C1-C4alkyl, C1-C3haloalkyl, C1-C3alkoxy, C3-C6cycloalkyl, hydroxyl, cyano, aldehydo, nitro, amino, thfluoroeththio; n is selected from 0, 1 or 2.

4. The compound of formula (I) according to claim 1, characterized in that, wherein R1is selected from CH2CF3, CH2CH2CF3; R2, R4are independently from each other selected from hydrogen, fluorine, chlorine, bromine, methyl, cyano; R3is selected from hydrogen; R5is selected from hydrogen; R6is selected from hydrogen, methylcyano, methyl, ethyl, propyl, cyclopropylmethyl, cyclobutylmethyl, cyclopropylethyl, cyclobutylethyl, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, phenylcarbonyl, thfluoromethylsulfinyl, thfluoromethylsulfonyl, oxalyl; Q is arbitrarily selected from and can be mono- or poly-substituted with one or more identical or different substituents selected from the group consisting of fluorine, chlorine, methyl, ethyl, propyl, methoxy, thfluoromethyl, thfluoroethyl, thbutyl, cyclopropyl, hydroxyl, cyano, aldehydo, nitro, amino, thfluoroeththio; n is selected from 0, 1 or 2.

5. The compound of formula (I) according to claim 4, characterized in that wherein R1is selected from CH2CF3, CH2CH2CF3; R2is selected from fluorine, chlorine, bromine, methyl, cyano; R3is selected from hydrogen; R4is selected from fluorine, chlorine, bromine, methyl, cyano; R5is selected from hydrogen; R6is selected from hydrogen, methyl cyano, methyl, ethyl, cyclopropylmethyl, methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, cyclopropylcarbonyl, phenylcarbonyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, oxalyl; Q is selected from Q1and can be mono- or poly-substituted by one or more identical or different substituents selected from fluorine, chlorine, methyl, methoxy, trifluoromethyl, cyclopropyl, hydroxyl, cyano, aldehydo, nitro, amino, trifluoroethylthio; or Q is optionally selected from Q2, Q3or Q4and can be mono- or poly-substituted by one or more identical or different substituents selected from fluorine, chlorine, hydroxyl, trifluoromethyl, cyano, nitro; n is selected from 0, 1 or 2.

6. The compound of formula (I) according to claim 4, characterized in that wherein R1is selected from CH2CF3, CH2CH2CF3; R2is selected from fluorine, chlorine, methyl; R3is selected from hydrogen; R4is selected from fluorine, chlorine; R5is selected from hydrogen; R6is selected from hydrogen, methyl, methylcarbonyl; Q is optionally selected from Q1, Q2, Q3or Q4and can be mono- or poly-substituted by one or more identical or different substituents selected from fluorine, chlorine, trifluoromethyl, nitro, cyano; n is selected from 0, 1 or 2.

7. An agrochemical formulation comprising a compound of formula (I) according to claim 1 and an extender and / or a surface-active agent.

8. An agrochemical formulation according to claim 7, further comprising a further agrochemically active ingredient.

9. A method for controlling animal pest mites, characterized by, Bringing a compound of formula (I) according to claim 1 or an agrochemical formulation according to claim 7 or 8 into the vicinity of animal pest mites and / or their habitat.

10. Use of a compound of formula (I) according to claim 1 or an agrochemical formulation according to claim 7 or 8 for controlling plant pest mites.

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