N-substituted phenylpyrazole derivative and preparation and use thereof

Abstract

The present invention relates to an N-substituted phenylpyrazole derivative, and a preparation and a use thereof. Specifically, the present invention relates to a compound of formula (I) as the N-substituted phenylpyrazole derivative or an isotope-labeled compound thereof, or an optical isomer, geometric isomer, tautomer or isomer mixture thereof, or an acceptable salt thereof, and a use of said compound in the preparation of an insecticide for pest control. The compound can achieve better pest control effects at lower doses, especially for pests of the orders Lepidoptera, Coleoptera, Homoptera, Hemiptera, Thysanoptera, Isoptera, Diptera, Hymenoptera, Mallophaga, Anoplura, Orthoptera, Blattodea, Siphonaptera and Acarina, and the class Nematoda.

Description

An N-substituted phenylpyrazole derivative and its preparation and application Technical Field

[0001] The present invention relates to the field of insecticide, and in particular to an N-substituted phenylpyrazole derivative and a preparation and application thereof. Background Art

[0002] Although there are currently a variety of control measures in the field of insecticide, new, more effective and reasonable insecticidal compounds are constantly being explored and discovered. The present invention provides a new type of compound that can be further studied. Pyrazole compounds have excellent biological and physiological activities. In terms of medical care, animal health and plant protection, pyrazole compounds have shown a wide range of applications and development prospects. In particular, in terms of insecticide, these compounds have a different mechanism of action from most insecticides used in the field of pest control, which can solve the increasingly serious resistance problem. Because of this, pyrazole compounds have opened up new horizons for the development of medicinal chemistry and provided a new approach to the search for new, highly effective and low-toxic insecticides.

[0003] Summary of the Invention

[0004] The present invention provides a phenylpyrazole derivative, and a composition comprising such a derivative, for use in controlling arthropod pests. In particular, such a compound has excellent control efficacy against a variety of pests, such as the diamondback moth, fall armyworm, armyworm, Spodoptera litura, beet armyworm, striped stem borer, black cutworm, cat flea, boophilus microplus, Rhipicephalus sanguineus, Bradygia leucoderma, Aedes albopictus, and American cockroach, while also exhibiting low toxicity and more targeted insecticide activity. These compounds are expected to address the low efficiency and high toxicity of current pesticides.

[0005] In a first aspect, the present invention provides a compound of formula (I) or an isotope-labeled compound thereof, or an optical isomer, geometric isomer, tautomer or isomer mixture thereof, or a pesticidally acceptable salt thereof as a phenylpyrazole derivative,

[0006] in,

[0007] X1, X2, X3, X4 are each independently selected from hydrogen, halogen, hydroxy, nitro, amino, cyano, carboxyl, C 1-6 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, C 1-6 Halogenated alkyl, C 1-6 Alkoxy or C 1-6 haloalkoxy;

[0008] R1 is selected from hydrogen, halogen, hydroxy, cyano, nitro, amino, carboxyl, C 1-6 Alkyl, C 2-6Alkenyl, C 2-6 Alkynyl, C 1-6 Halogenated alkyl, C 2-6 Halogenated alkenyl, C 2-6 Haloalkynyl, C 6-10 Aryl, C 6-10 Halogenated aryl, C 6-10 Aryl-C 1-6 Alkyl or C 6-10 Halogenated aryl-C 1-6 alkyl;

[0009] R2 is selected from hydrogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-12 Cycloalkyl, C 3-6 Heterocyclic group, C 6-10 Aryl, C 5-12 Heteroaryl, C 1-6 Alkoxy C 1-6 Alkyl, C 3-12 Cycloalkyl C 1-6 Alkyl, and may be monosubstituted or polysubstituted by one or more identical or different substituents selected from: halogen, cyano, C 1-6 Alkyl, C 1-6 alkyl halide;

[0010] Q is selected from C 1-6 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-12 Cycloalkyl, C 3-6 Heterocyclic group, C 6-10 Aryl, C 5-12 Heteroaryl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylthio C 1-6 Alkyl, C 3-12 Cycloalkyl C 1-6 Alkyl, C 3-6 Heterocyclyl C 1-6 Alkyl, C 6-10 Aryl C 1-6 Alkyl, C 5-12 Heteroaryl C 1-6 Alkyl, C 6-10 Aryloxy C 1-6 Alkyl, C 5-12 Heteroaryloxy C 1-6 Alkyl, and may be monosubstituted or polysubstituted by one or more identical or different substituents selected from: halogen, cyano, nitro, C 1-6 Alkyl, C 1-6 Alkoxy, C1-6 Halogenated alkyl, C 1-6 Alkoxycarbonyl, C 1-3 Alkylamino, C 6-10 Aryl.

[0011] In one embodiment of the present invention,

[0012] X1, X2, X3, X4 are each independently selected from hydrogen, halogen, hydroxy, nitro, amino, cyano, carboxyl, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 1-4 Halogenated alkyl, C 1-4 Alkoxy or C 1-4 haloalkoxy;

[0013] R1 is selected from hydrogen, halogen, hydroxy, cyano, nitro, amino, carboxyl, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 1-4 Halogenated alkyl, C 2-4 Halogenated alkenyl, C 2-4 Haloalkynyl, C 6-10 Aryl, C 6-10 Halogenated aryl, C 6-10 Aryl-C 1-3 Alkyl or C 6-10 Halogenated aryl-C 1-3 alkyl;

[0014] R2 is selected from hydrogen, C 1-3 Alkyl, C 1-3 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-12 Cycloalkyl, C 3-6 Heterocyclic, aryl, C 5-12 Heteroaryl, C 1-3 Alkoxy C 1-3 Alkyl, C 3-12 Cycloalkyl C 1-3 Alkyl, which may be monosubstituted or polysubstituted by one or more identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, C 1-3 Alkyl, C 1-3 alkyl halide;

[0015] Q is selected from C 1-6 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-12 Cycloalkyl, C 3-6 Heterocyclic group, C 6-10 Aryl, C 5-12Heteroaryl, C 1-3 Alkoxy C 1-3 Alkyl, C 1-3 Alkylthio C 1-3 Alkyl, C 3-12 Cycloalkyl C 1-3 Alkyl, C 3-6 Heterocyclyl C 1-3 Alkyl, C 6-10 Aryl C 1-3 Alkyl, C 5-12 Heteroaryl C 1-3 Alkyl, C 6-10 Aryloxy C 1-3 Alkyl, C 5-12 Heteroaryloxy C 1-3 Alkyl, and may be monosubstituted or polysubstituted by one or more identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, C 1-3 Alkyl, C 1-3 Alkoxy, C 1-3 Halogenated alkyl, C 1-3 Alkoxycarbonyl, C 1-3 Alkylamino, C 6-10 Aryl.

[0016] In another embodiment of the present invention, wherein,

[0017] X1, X2, X3, X4 are each independently selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, amino, carboxyl, C 1-4 Alkyl, C 1-4 Halogenated alkyl, C 1-4 Alkoxy or C 1-4 haloalkoxy;

[0018] R1 is selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, amino, carboxyl, C 1-4 Alkyl or C 1-4 alkyl halide;

[0019] R2 is selected from hydrogen, C 1-3 Alkyl, C 1-3 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Heterocyclic group, C 1-3 Alkoxy C 1-3 Alkyl, C 3-6 Cycloalkyl C 1-3 Alkyl, which may be monosubstituted or polysubstituted by one or more identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, C 1-3 Alkyl, C 1-3 alkyl halide;

[0020] Q is selected from C 1-6Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Heterocyclic group, C 6-10 Aryl, C 5-12 Heteroaryl, C 1-3 Alkoxy C 1-3 Alkyl, C 1-3 Alkylthio C 1-3 Alkyl, C 3-6 Cycloalkyl C 1-3 Alkyl, C 3-6 Heterocyclyl C 1-3 Alkyl, C 6-10 Aryl C 1-3 Alkyl, C 5-12 Heteroaryl C 1-3 Alkyl, and may be monosubstituted or polysubstituted by one or more identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, C 1-3 Alkyl, C 1-3 Alkoxy, C 1-3 Halogenated alkyl, C 1-3 Alkoxycarbonyl, C 1-3 Alkylamino.

[0021] In another preferred embodiment of the present invention,

[0022] X1, X2, X3, X4 are each independently selected from hydrogen, fluorine, chlorine, bromine, iodine, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -C(CH3)3, -CH2Cl, -CHF2, -CF 3、 -CH(CF3)2, -CF(CH3)2, -C(CF3)3, -CH2F, -CF2CH3, -CF(CF3)2, -C(OH)(CF3)2, -C(OCH3)(CF3)2;

[0023] R1 is selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, amino, carboxyl, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -C(CH3)3, -CH2Cl, -CHF2, -CF3;

[0024] R2 is selected from hydrogen, C 1-3 Alkyl, C 1-3 Alkoxy, C 3-6 Cycloalkyl, C 1-3 Alkoxy C 1-3 Alkyl, C 3-6 Cycloalkyl C 1-3Alkyl, which may be monosubstituted or polysubstituted by one or more identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, C 1-3 Alkyl, C 1-3 alkyl halide;

[0025] Q is selected from C 1-6 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 1-3 Alkoxy C 1-3 Alkyl, C 1-3 Alkylthio C 1-3 Alkyl, C 3-6 Cycloalkyl C 1-3 Alkyl or the following groups,

[0026] And it may be mono- or poly-substituted by one or more identical or different substituents selected from: fluorine, chlorine, bromine, cyano, nitro, -CH3, -CH2CH3, -CHF2, -CF3, -OCH3, -OCH2CH3, -OCF3, -NHCH3, -N(CH3)2.

[0027] In another preferred embodiment of the present invention,

[0028] X1, X2, X4 are each independently selected from hydrogen, fluorine, chlorine, bromine, and iodine;

[0029] X3 is selected from -CH2CH2CH3, -CH(CH3)2, -CH(CF3)2, -CF(CH3)2, -CF(CF3)2;

[0030] R1 is selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, and amino;

[0031] R2 is selected from hydrogen, C 1-3 Alkyl, C 3-6 Cycloalkyl, which may be mono- or poly-substituted by one or more identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, and cyano;

[0032] Q is selected from C 1-6 Alkyl, C 2-4 Alkenyl, C 3-6 Cycloalkyl, C 1-3 Alkoxy C 1-3 Alkyl, C 1-3 Alkylthio C 1-3 Alkyl or the following groups,

[0033] And it may be mono- or poly-substituted by one or more identical or different substituents, wherein the substituents are selected from: fluorine, chlorine, bromine, cyano, nitro, -CH3, -CH2CH3, -CF3, -OCH3, -OCH2CH3, -OCF3, -NHCH3, -N(CH3)2.

[0034] In another preferred embodiment of the present invention, the compound of formula (I) has the following structure:

[0035] In another aspect, the present invention relates to a composition comprising at least one compound according to the present invention and at least one pesticidally acceptable adjuvant.

[0036] In yet another aspect, the present invention relates to use of the compound or composition of the present invention as a pest control agent in agriculture, forestry or horticulture.

[0037] Furthermore, in some embodiments, the present invention relates to the use of the compound of the present invention or the composition of the present invention in preventing and / or controlling pests, wherein the pests include at least one of the diamondback moth, fall armyworm, Spodoptera litura, beet armyworm, armyworm, striped stem borer, black cutworm, cat flea, boophilus microplus, Rhipicephalus sanguineus, Bradygia leekensis, Aedes albopictus, and American cockroach.

[0038] In yet another aspect, the present invention relates to a method for controlling pests, comprising applying an effective amount of the compound or composition of the present invention to the pests or the locus of the pests.

[0039] Detailed description of the invention

[0040] Definitions and General Terms

[0041] Certain embodiments of the present invention are now described in detail, examples of which are illustrated by the accompanying structural formulas and chemical formulae. The definitions and preferences described in one aspect of the present invention apply equally to the other aspects. The embodiments of the various aspects of the present invention can be combined in various ways without departing from the subject matter and ideas of the present invention, and these combinations are also included within the scope of the present invention.

[0042] It will be further appreciated that certain features of the invention, which, for clarity, are described in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features of the invention, which, for brevity, are described in the context of a single embodiment, may also be provided separately or in any suitable subcombination.

[0043] Unless otherwise specified, all technical terms used in the present invention have the same meaning as commonly understood by those skilled in the art to which the present invention belongs. All patents and publications related to the present invention are incorporated herein by reference in their entirety.

[0044] Unless otherwise indicated, the following definitions used in the present invention shall apply. For purposes of the present invention, chemical elements are consistent with the Periodic Table of the Elements, CAS version, and Handbook of Chemistry and Physics, 75th edition, 1994. In addition, general principles of organic chemistry can be found in "Organic Chemistry", Thomas Sorrell, University Science Books, Sausalito: 1999, and "March's Advanced Organic Chemistry" by Michael B. Smith and Jerry March, John Wiley & Sons, New York: 2007, the entire contents of which are incorporated herein by reference.

[0045] Unless otherwise specified or clearly contradicted by context, the articles "a," "an," and "the" as used herein are intended to include "at least one" or "one or more." Thus, as used herein, these articles refer to one or more than one (i.e., at least one) of the objects. For example, "a component" refers to one or more components, i.e., more than one component may be contemplated for use or use in implementing the described embodiment.

[0046] As described herein, the compounds of the present invention may be optionally substituted with one or more substituents, such as the compounds of the general formula above, or as specifically exemplified in the Examples, subclasses, and classes of compounds encompassed by the present invention. It should be understood that the term "optionally substituted" is used interchangeably with the term "substituted or unsubstituted." In general, the term "substituted" means that one or more hydrogen atoms in a given structure are replaced with a specified substituent. Unless otherwise indicated, an optional substituent group may be substituted at each substitutable position of the group. When more than one position in a given formula can be substituted with one or more substituents selected from a specified group, the substituents may be the same or different at each position. Specifically, examples of "one or more" refer to 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. The substituents can be, but are not limited to, deuterium, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, amino, carboxyl, alkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, alkoxyalkylamino, aryloxy, heteroaryloxy, heterocyclyloxy, arylalkoxy, heteroarylalkoxy, heterocyclylalkoxy, cycloalkylalkoxy, cycloalkylalkylamino, alkylthio, haloalkyl, haloalkoxy, hydroxy-substituted alkyl, hydroxy-substituted alkylamino, cyano-substituted alkyl, cyano-substituted alkoxy, cyano-substituted alkylamino, amino-substituted alkyl, alkylacyl, heteroalkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heterocyclylacyl, aryl, arylalkyl, arylamino, heteroaryl, heteroarylalkyl, heteroarylamino, amido, sulfonyl, aminosulfonyl, and the like.

[0047] In addition, it should be noted that, unless otherwise explicitly stated, the description methods used in the present invention such as "each...independently is" and "...each independently is" and "...independently is" can be interchanged and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or that in the same group, the specific options expressed by the same symbols do not affect each other.

[0048] In various parts of this specification, substituents of compounds disclosed herein are disclosed in terms of group types or ranges. It is specifically noted that the present invention includes every independent subcombination of the individual members of these group types and ranges. For example, the term "C1-C6 alkyl" or "C 1-6 "Alkyl" specifically refers to methyl, ethyl, C3 alkyl, C4 alkyl, C5 alkyl and C6 alkyl as disclosed independently.

[0049] As used herein, the term "alkyl" or "alkyl group" refers to a saturated, linear or branched, monovalent hydrocarbon radical containing 1 to 6 carbon atoms, optionally substituted with one or more substituents described herein. Unless otherwise specified, an alkyl group contains 1 to 6 carbon atoms. In one embodiment, an alkyl group contains 1 to 5 carbon atoms; in another embodiment, an alkyl group contains 1 to 4 carbon atoms; and in another embodiment, an alkyl group contains 1 to 3 carbon atoms.

[0050] Examples of alkyl groups include, but are not limited to, methyl (Me, -CH3), ethyl (Et, -CH2CH3), n-propyl (n-Pr, -CH2CH2CH3), isopropyl (i-Pr, -CH(CH3)2), n-butyl (n-Bu, -CH2CH2CH2CH3), isobutyl (i-Bu, -CH2CH(CH3)2), sec-butyl (s-Bu, -CH(CH3)CH2CH3), tert-butyl (t-Bu, -C(CH3)3), n-butyl Pentyl (-CH2CH2CH2CH2CH3), 2-pentyl (-CH(CH3)CH2CH2CH3), 3-pentyl (-CH(CH2CH3)2), 2-methyl-2-butyl (-C(CH3)2CH2CH3), 3-methyl-2-butyl (-CH(CH3)CH(CH3)2), 3-methyl-1-butyl (-CH2CH2CH(CH3)2), 2-methyl-1-butyl (-CH2CH(CH3)CH2CH3), and the like.

[0051] The term "alkoxy" refers to an alkyl group attached to the rest of the molecule via an oxygen atom, wherein the alkyl group has the meaning as defined herein. Examples of alkoxy groups include, but are not limited to, methoxy (MeO, -OCH3), ethoxy (EtO, -OCH2CH3), 1-propoxy (n-PrO, n-propoxy, -OCH2CH2CH3), 2-propoxy (i-PrO, i-propoxy, -OCH(CH3)2), and the like.

[0052] The term "halogen" refers to fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

[0053] The term "haloalkyl" refers to an alkyl group substituted with one or more halogen atoms, examples of which include, but are not limited to, -CF3, -CHF2, -CH2Cl, -CH2CF3, -CH2CHF2, -CH2CH2CF3 and the like.

[0054] The term "haloalkoxy" means an alkoxy group substituted by one or more halogen atoms, examples of which include, but are not limited to, -OCF3, -OCHF2, -OCHCl2, -OCH2CHF2, -OCH2CHCl2, -OCH(CH3)CHF2, etc.

[0055] The term "alkenyl" refers to a linear or branched monovalent hydrocarbon radical containing 2 to 6 carbon atoms, wherein there is at least one site of unsaturation, i.e., a carbon-carbon sp 2 Double bond, wherein the alkenyl group can be optionally substituted with one or more substituents described herein, including "cis" and "tans" positioning, or "E" and "Z" positioning. In one embodiment, the alkenyl group contains 2-5 carbon atoms; in another embodiment, the alkenyl group contains 2-4 carbon atoms; in yet another embodiment, the alkenyl group contains 2-3 carbon atoms. Examples of alkenyl groups include, but are not limited to, vinyl (-CH=CH2), allyl (-CH2CH=CH2), propenyl (CH3-CH=CH-), oxobutenyl (CH3-C(=O)-CH=CH-), and the like.

[0056] The term "alkynyl" refers to a linear or branched monovalent hydrocarbon radical containing 2-6 carbon atoms, wherein at least one carbon-carbon sp triple bond is present, wherein the alkynyl group may be optionally substituted with one or more substituents described herein. In one embodiment, the alkynyl group contains 2-5 carbon atoms; in one embodiment, the alkynyl group contains 2-4 carbon atoms; in another embodiment, the alkynyl group contains 2-3 carbon atoms. Examples of alkynyl groups include, but are not limited to, -C≡CH, -C≡CCH3, -CH2-C≡CH, -CH2-C≡CCH3, -CH2CH2-C≡CH, -CH2-C≡CCH2CH3, -CH2CH2-C≡CCH3, and the like.

[0057] As used herein, the term "unsaturated" means that the group contains one or more degrees of unsaturation.

[0058] The term "heteroaryl" refers to monocyclic, bicyclic, and tricyclic ring systems containing 5-12 ring atoms, or 5-10 ring atoms, or 5-6 ring atoms, wherein at least one ring system is aromatic and at least one ring system contains one or more heteroatoms, wherein each ring system contains 5-7 ring atoms and has one or more points of attachment to the rest of the molecule. The term "heteroaryl" can be used interchangeably with the terms "heteroaromatic ring" or "heteroaromatic compound." The heteroaryl group is optionally substituted with one or more substituents described herein.

[0059] The term "heteroatom" refers to O, S, N, P and Si, including N, S and P in any oxidation state; in the form of primary, secondary, tertiary amines and quaternary ammonium salts; or in the form of a nitrogen atom in a heterocyclic ring substituted with a hydrogen, for example, N (such as N in 3,4-dihydro-2H-pyrrolyl), NH (such as NH in pyrrolidinyl) or NR (such as NR in N-substituted pyrrolidinyl).

[0060] In one embodiment, the 5-10 atom heteroaryl group contains 1, 2, 3 or 4 heteroatoms independently selected from O, S and N.

[0061] In another embodiment, the ring atoms of the heteroaryl group contain 1-9 carbon atoms and 1-4 heteroatoms selected from N, O, or S; in another embodiment, the ring atoms of the heteroaryl group contain 1-5 carbon atoms and 1-4 heteroatoms selected from N, O, or S.

[0062] In another embodiment, heteroaryl represents a 5-membered or 6-membered heteroaryl containing 1-4 N heteroatoms; in another embodiment, heteroaryl represents a 5-membered heteroaryl containing 1-3 heteroatoms selected from N, O or S; in another embodiment, heteroaryl represents a 5-membered heteroaryl containing 1-3 heteroatoms selected from N or O; in another embodiment, heteroaryl represents a 5-membered heteroaryl containing 1-3 heteroatoms selected from N or S.

[0063] Examples of heteroaryl groups include, but are not limited to, 2-furyl, 3-furyl, N-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, pyridazinyl (e.g., 3-pyridazinyl), 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, tetrazolyl (e.g., 5-tetrazolyl), triazolyl (e.g., 2- and 5-triazolyl), 2-thiophenyl, 3-thiophenyl, pyrazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,3-triazolyl, 1,2,3-thiodiazolyl, 1,3,4-thiodiazolyl, 1,2,5-thiodiazolyl, pyrazinyl, 1,3,5-triazinyl, pyrimidinone, pyridinone; and also include, but are not limited to, the following bicyclic rings: benzimidazolyl, benzofuranyl, benzotetrahydrofuranyl, benzothiophenyl, indolyl (such as 2-indolyl), and the like.

[0064] The term "cycloalkyl" refers to a monovalent or multivalent saturated monocyclic, bicyclic, or tricyclic ring system containing 3-12 carbon atoms. In one embodiment, the cycloalkyl group contains 3-12 carbon atoms; in another embodiment, the cycloalkyl group contains 3-10 carbon atoms; in another embodiment, the cycloalkyl group contains 3-8 carbon atoms; and in yet another embodiment, the cycloalkyl group contains 3-6 carbon atoms. The cycloalkyl group is optionally substituted with one or more substituents described herein. Examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, adamantyl, and the like.

[0065] The terms "heterocyclyl" and "heterocycle" are used interchangeably herein and refer to a saturated or partially unsaturated monocyclic, bicyclic, or tricyclic ring containing 3 to 15 ring atoms, wherein the monocyclic, bicyclic, or tricyclic ring does not contain an aromatic ring and at least one ring atom is selected from nitrogen, sulfur, and oxygen atoms. Unless otherwise specified, a heterocyclyl group can be a carbon group or a nitrogen group, and a -CH2- group can be optionally replaced by a -C(=O)- group. A sulfur atom of the ring can be optionally oxidized to an S-oxide. A nitrogen atom of the ring can be optionally oxidized to an N-oxide. Examples of heterocyclic groups include, but are not limited to, oxiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl (e.g., 2-pyrrolidinyl), 2-pyrrolinyl, 3-pyrrolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, tetrahydrofuranyl, dihydrofuranyl, tetrahydrothiophenyl, dihydrothiophenyl, 1,3-dioxolane, dithiolanyl, tetrahydropyranyl, dihydropyranyl, 2H-pyranyl, 4H-pyranyl, pyranyl, tetrahydrothiopyranyl, piperidinyl (2-piperidinyl, 3-piperidinyl, 4-piperidinyl), morpholinyl, thiomorpholinyl, (1-oxo)-thiomorpholinyl, (1,1-dioxo)-thiomorpholinyl, piperazinyl, dioxanyl, dithianyl, thioxanyl, homopiperazinyl, homopiperidinyl, oxepanyl, thiepanyl, 2-oxa-5-azabicyclo[2.2.1]hept-5-yl, tetrahydropyridinyl. Examples of heterocyclic groups in which the -CH2- group is replaced by -C(=O)- include, but are not limited to, 2-oxopyrrolidinyl, oxo-1,3-thiazolidinyl, 2-piperidonyl, 3,5-dioxopiperidinyl. Examples of heterocyclic groups in which the sulfur atom is oxidized include, but are not limited to, sulfolane and 1,1-dioxothiomorpholinyl. The heterocyclyl group is optionally substituted with one or more substituents described herein.

[0066] The term "aryl" refers to monocyclic, bicyclic, and tricyclic carbon ring systems containing 6-14 ring atoms, or 6-12 ring atoms, or 6-10 ring atoms, wherein at least one ring system is aromatic, wherein each ring system comprises a ring of 3-7 atoms and has one or more points of attachment to the rest of the molecule. The term "aryl" can be used interchangeably with the term "aromatic ring". Examples of aryl groups include phenyl, indenyl, naphthyl, and anthracenyl. The aryl groups are optionally substituted with one or more substituents described herein.

[0067] Salts of the compounds of the present invention include those derived from alkali metals or alkaline earth metals and those derived from ammonia and amines. Preferred cations include sodium, potassium, magnesium and those having the formula N + (R AA R BB R CC R DD ) of an ammonium cation, wherein R AA 、R BB 、R CC and R DD Independently selected from hydrogen, C1-C6 alkyl and C1-C6 hydroxyalkyl. Salts of compounds of formula (I) can be prepared by treating the compound of formula (I) with a metal hydroxide (e.g., sodium hydroxide) or an amine (e.g., ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine or benzylamine).

[0068] When the compounds of the present invention contain a basic moiety, acceptable salts may be formed with organic and inorganic acids such as acetic acid, propionic acid, lactic acid, citric acid, tartaric acid, succinic acid, fumaric acid, maleic acid, malonic acid, mandelic acid, malic acid, phthalic acid, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, methanesulfonic acid, naphthalenesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, camphorsulfonic acid, and similarly known acceptable acids.

[0069] Compositions and formulations of the compounds of the present invention

[0070] The compound of the present invention can generally be used as an active ingredient of pesticides in compositions and / or formulations, and usually further comprises pharmaceutically common adjuvants. The adjuvants include surfactants and carriers.

[0071] The above-mentioned surfactant can be various surfactants known in the field of pesticide formulations. In the present invention, it is preferably one or more of an emulsifier, a dispersant and a wetting agent.

[0072] Other carriers besides the above-mentioned surfactants may be various carriers known in the field of pharmaceutical dosage forms, including various silicates, carbonates, sulfates, oxides, phosphates, plant carriers, and synthetic carriers. Specifically, for example, one or more of white carbon black, kaolin, diatomaceous earth, clay, talc, organobentonite, pumice, titanium dioxide, dextrin, cellulose powder, light calcium carbonate, soluble starch, corn starch, sawdust powder, urea, amine fertilizer, a mixture of urea and amine fertilizer, glucose, maltose, sucrose, anhydrous potassium carbonate, anhydrous sodium carbonate, anhydrous potassium bicarbonate, anhydrous sodium bicarbonate, attapulgite, a mixture of anhydrous potassium carbonate and anhydrous potassium bicarbonate, and a mixture of anhydrous sodium carbonate and anhydrous sodium bicarbonate.

[0073] The emulsifier can be any of various emulsifiers known in the field of pharmaceutical dosage forms. Specifically, the emulsifier can be one or more of calcium dodecylbenzenesulfonate, triphenyl phenol polyoxyethylene ether phosphate, fatty alcohol polyoxyethylene ether, alkylphenol polyoxyethylene ether, alkylphenol polyoxyethylene polyoxypropylene ether, fatty amine, ethylene oxide adduct of fatty amide, fatty acid polyoxyethylene ester, rosin acid ethylene oxide adduct, polyol fatty acid ester and ethylene oxide adduct thereof, styrylphenyl polyoxyethylene ether, alkylphenol formaldehyde resin polyoxyethylene ether, terminal hydroxyl polyoxyethylene polyoxypropylene ether, styrylphenol formaldehyde resin polyoxyethylene polyoxypropylene ether and castor oil polyoxyethylene ether.

[0074] The dispersant can be any of various dispersants known in the field of pharmaceutical dosage forms. Specifically, the dispersant is one or more of sodium salt of acrylic acid homopolymer, disodium maleate, sodium salt of naphthalenesulfonic acid formaldehyde condensate, rosin block polyoxyethylene ether polyoxypropylene ether sulfonate, hydroxyl-terminated polyoxyethylene polyoxypropylene ether block copolymer, triphenylphenol polyoxyethylene ether phosphate, fatty alcohol polyoxyethylene ether phosphate and sodium salt of p-hydroxyphenyl lignin sulfonate.

[0075] The wetting agent can be any wetting agent known in the field of pharmaceutical dosage forms. Specifically, the wetting agent can be one or more of sodium lauryl sulfate, sodium secondary alkyl sulfate, sodium dodecylbenzene sulfonate, fatty alcohol polyoxyethylene ether, alkyl naphthalene sulfonate, and alkylphenol resin polyoxyethylene ether sulfate.

[0076] According to the insecticide composition of the present invention, the insecticide composition may further contain various formulation adjuvants commonly used in the field of pharmaceutical dosage forms. Specifically, the formulation adjuvant may be one or more of solvents, cosolvents, thickeners, antifreeze agents, capsule materials, protective agents, defoaming agents, disintegrants, stabilizers, preservatives and binders.

[0077] The above-mentioned solvent can be various solvents known in the field of pharmaceutical dosage forms. Specifically, the solvent can be one or more of an organic solvent, vegetable oil, mineral oil, solvent oil and water.

[0078] The organic solvent includes one or more of N-methylpyrrolidone, tetrahydrofuran, dimethyl sulfoxide, N,N-dimethyldecylamide, N,N-dimethylformamide, trimethylbenzene, tetramethylbenzene, xylene, toluene, octane, heptane, methanol, isopropanol, n-butanol, tetrahydrofurfuryl alcohol, tributyl phosphate, 1,4-dioxane and cyclohexanone.

[0079] The vegetable oil includes one or more of methylated vegetable oil, rosin-based vegetable oil, turpentine, epoxidized soybean oil, soybean oil, peanut oil, rapeseed oil, castor oil, corn oil and pine nut oil.

[0080] The mineral oil includes one or more of liquid wax, motor oil, kerosene and lubricating oil.

[0081] At the same time, the above solvents can also be used as co-solvents.

[0082] The antifreeze agent can be any antifreeze agent known in the field of pharmaceutical dosage forms. In the present invention, the antifreeze agent is preferably one or more of ethylene glycol, propylene glycol, glycerol and urea.

[0083] The thickener can be any of various thickeners known in the field of pharmaceutical dosage forms. Specifically, the thickener can be one or more of xanthan gum, polyvinyl alcohol, polypropylene alcohol, polyethylene glycol, white carbon black, diatomaceous earth, kaolin, clay, sodium alginate, magnesium aluminum silicate, sodium aluminum silicate, carboxymethyl cellulose, sodium hydroxypropyl cellulose and organic bentonite.

[0084] The capsule material can be any capsule material known in the field of pharmaceutical dosage forms. In the present invention, it is preferably one or more of polyurethane, polyurea and urea-formaldehyde resin.

[0085] The protective agent can be any protective agent known in the field of pharmaceutical dosage forms, and in the present invention, polyvinyl alcohol and / or polyethylene glycol are preferred.

[0086] The defoaming agent can be any of various defoaming agents known in the field of pharmaceutical dosage forms. In the present invention, the defoaming agent is preferably one or more of organosiloxane, tributyl phosphate and silicone.

[0087] The stabilizer is selected from one or more of triphenyl phosphite, epichlorohydrin and acetic anhydride.

[0088] The preservative is selected from one or more of benzoic acid, sodium benzoate, 1,2-benzisothiazolin-3-one (BIT), kasone and potassium sorbate.

[0089] The present invention also provides a formulation prepared from the above-mentioned insecticide composition, wherein the formulation is in the form of an emulsifiable concentrate, an aqueous emulsion, a microemulsion, a soluble liquid, an aqueous suspension, a suspoemulsion, an ultra-low volume spray, an oil suspension, a microcapsule suspension, a water-film-spreading oil, a wettable powder, a water-dispersible granule, a dry suspension, a soluble powder, a soluble granule, an emulsifiable powder, an emulsifiable granule, a granule, a solid microcapsule formulation, an effervescent tablet, an effervescent granule, a water-floating dispersible granule, or a seed coating. All of the above-mentioned formulations can be prepared by conventional methods in the art.

[0090] The insecticide composition of the present invention can be provided in the form of a finished formulation, that is, the various substances in the composition are already mixed; it can also be provided in the form of a separate formulation, which can be mixed in a bucket or tank before use and selectively mixed with water for dilution according to the desired concentration of the active substance.

[0091] For additional information related to the field of formulations, see T. S. Woods, "The Formulator's Toolbox—Product Forms for Modern Agriculture," in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, edited by T. Brooks and T. R. Roberts, Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361 at column 6, lines 16 to column 7, line 19, and Examples 10-41; U.S. Pat. No. 3,309,192 at column 5, lines 43 to column 7, line 62, and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, and 169-182; U.S. Pat. No. 2,891,855 at column 3, lines 66 to column 5, line 17, and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp. 81-96; Hance et al., Weed Control Handbook, 8th ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000.

[0092] Application of the compounds and compositions of the present invention

[0093] The compounds and / or compositions of the present invention are suitable for controlling pests in animals and plants such as arthropods, gastropods and nematodes, including but not limited to:

[0094] From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp. spp.), Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvatalugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., and Psylla spp.

[0095] Hemiptera: Planthoppers (Delphacidae) such as the brown planthopper (Nilaparvata lugens) and the small gray planthopper (Laodelphax striatellus); leafhoppers (Deltocephalidae) such as the green rice leafhopper (Nephotettix cincticeps); aphids (Aphididae) such as the cotton aphid (Aphis gossypii) and the alfalfa aphid (Aphis craccivora Koch); Pentatomidae such as the flower bug (Nezara antennata); whiteflies (Aleyrodidae) such as the greenhouse whitefly (Trialeurodes vaporariorum); scale insects (Coccidae) such as the California red scale (Aonidiella aurantii); Tingidae; Homoptera, Psyllidea;

[0096] Lepidoptera: Pyralidae such as Chilo suppressalis; Noctuidae such as Spodoptera litura, Pseudaletia separata, Heliothis spp., and Helicoverpa spp.; Pieridae such as Pieris rapae; Tortricidae such as Adoxophyes; Gracilariidae such as Caloptilia theivora and Phyllonorycter ringoneella; Carposinidae such as Carposina niponensis; Lyonetiidae such as Lyonetia spp. spp.); tussock moths (Lymantriidae), such as Lymantria spp. and Euproctis spp.; nest moths (Yponomeutidae), such as Plutella xylostella (diamondback moth); wheat moths (Gelechiidae), such as Pectinophora gossypiella (red bell wheat moth) and Phthorimaea operculella (potato wheat moth); lamp moths (Arctiidae), such as Hyphantria cunea (American white moth); and grain moths (Tineidae), such as Tinea translucens (clothes moth) and Tineola bisselliella (curtain moth);

[0097] Thysanoptera: Frankliniella occidentalis (Western Flower Thrips), Thrips palmi (Palm Thrips), Scirtothrips dorsalis (Yellow Hard Thrips), Thrips tabaci (Tobacco Thrips), Frankliniella intonsa (Beautiful Flower Thrips), and Frankliniella fusca (Potato Thrips);

[0098] Diptera: Musca domestica, Culex popiens pallens, Tabanus trigonus, Hylemya anitqua, Hylemya platura, Anopheles sinensis, Aedes albopictus, Bradysia odoriphaga Yang et Zhang, Agromyza oryzae, Hydrellia griseola, Chlorops oryzae, Dacus cucurbitae, Ceratitis capitata, and Liriomyza trifolii;

[0099] Coleoptera: Epilachna vigintioctopunctata, Phyllotreta striolata, Oulema oryzae, Echinocnemus squameus, Lissorhoptrus oryzophilus, Anthonomus grandis, Callosobruchus chinensis, Sphenophorus venatus, Popillia japonica, Anomala cuprea, Diabrotica spp., Leptinotarsa ​​decemlineata, Agriotes spp., Lasioderma serricorne, Anthrenus verbasci, Tribolium castaneum), brown powder beetle (Lyctus brunneus), white-spotted longhorn beetle (Anoplophora malasiaca), and vertical pit cutting beetle (Tomicus piniperda);

[0100] Orthoptera: East Asian migratory locust (Locusta migratoria), African mole cricket (Gryllotalpa afficana), Hokkaido rice locust (Oxya yezoensis), and Japanese rice locust (Oxya japanica);

[0101] Hymenoptera: Athalia rosae, Acromyrmex spp., and Solenopsis spp.;

[0102] Nematodes: Aphelenchoides besseyi (rice stem tip nematode), Nothotylenchus acris (strawberry bud nematode), Heterodera glycines (soybean cyst nematode), Meloidogyne incognita (southern root knot nematode), Pratylenchus penetrans (Pratylenchus penetrans), and Nacobbus aberrans (abnormal pearl nematode);

[0103] Blattariae: German cockroach (Blattella germanica), black-breasted cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta Americana), brown-spotted cockroach (Periplaneta brunnea), and Oriental cockroach (Blatta orientalis);

[0104] Order Acarina: Tetranychidae (e.g., Tetranychus cinnabarinus, Tetranychusurticae, Panonychus citri, and Oligonychus spp.); Eriophyidae (e.g., Aculops pelekassi); Tarsonemidae; Tenuipalpidae; Tuckerellidae; Tuckerellidae Acaridae; Pyroglyphidae (e.g., Dermatophagoides farinae and Dermatophagoides ptrenyssnus); Cheyletidae, Cheyletus melakaensis; malaccensis) and cattle ticks (Boophilus spp.), Rhipicephalus sanguineus; and Dermanyssidae.

[0105] From the order of the Siphonapterida: Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; in particular, representative examples are Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tungapenetrans, and Xenopsylla cheopis.

[0106] Within the scope of the present invention, useful animals include the following species: mammals, livestock, poultry, such as cats, dogs, cows, sheep, horses, pigs, camels, donkeys, mules, deer, chickens, ducks, geese, rabbits, pigeons, etc.

[0107] Within the scope of the present invention, useful plants include the following plant species: cereals (wheat, barley, rye, oats, rice, corn, sorghum and related species); beets (sugar beet and fodder beet); pome, stone and soft fruits (apple, pear, plum, peach, almond, cherry, strawberry, raspberry and blackberry); legumes (lentil, bean, pea, soybean); oil crops (rape, mustard, olive, sunflower, coconut, castor oil plant, cocoa bean, peanut or soybean); cucurbits (squash, cucumber, melon). ; fiber plants (cotton, flax, hemp, jute); citrus fruits (oranges, lemons, grapefruits, mandarins); vegetables (spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, red peppers); laurel plants (avocado, cinnamon, camphor) or plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, grapevines, hops, bananas and natural rubber plants, as well as turf, ornamental and forest plants, such as flowers, shrubs, broad-leaved trees or evergreen trees, such as conifers, and plant propagation material.

[0108] The term "plant propagation material" should be understood as meaning reproductive parts of the plant, such as seeds, which can be used for the multiplication of the plant, and vegetative material, such as cuttings or tubers (for example potatoes).

[0109] The compounds and / or compositions of the present invention can kill pests by using an effective amount of active substance. In particular, when the effective amount of the compound of formula (I) is within 5g-5kg per hectare, preferably 10g-1kg per hectare, the pest control effect is better.

[0110] The present invention also relates to a method for controlling pests by applying the compounds or compositions of the present invention to seeds, plants or plant parts, fruits or the soil in which the plants grow. Application can be carried out before and after the seeds, plants or plant parts, fruits or the soil in which the plants grow are infested by the pests.

[0111] The term "effective amount" as used herein means an amount of a compound or composition according to the invention which is sufficient to control pests on cultivated plants or in the protection of materials without causing significant damage to the treated plants. This amount may vary within wide limits and depends on various factors such as the pest species, the cultivated plants or materials being treated, climatic conditions and the specific compound used.

[0112] The compounds and / or compositions of the present invention are simple to use by applying them to the pest or its growth medium. The dosage of the compounds and / or compositions of the present invention varies depending on weather conditions, formulation, timing of application, method of application, area of ​​application, target disease, target crop, and the like.

[0113] General synthesis process

[0114] The following schemes describe the preparation of the compounds of the present invention. Unless otherwise specified, the compounds of the present invention can be prepared in a variety of ways known to those skilled in the art of organic synthesis. Those skilled in the art can refer to the synthetic routes of the specific compounds of the specific embodiments of the present invention and make appropriate adjustments to the reaction raw materials and reaction conditions to obtain the synthetic methods of other compounds. The raw materials, reagents, etc. used to prepare the compounds of the present invention are all commercially available or can be prepared by conventional methods in the art. In this specification, if there is any difference between the chemical name and the chemical structure, the structure is dominant.

[0115] For the sake of simplicity, the "pyrazole derivatives", "compounds of formula (I)" or "compounds of the present invention" mentioned below may also include any isotope-labeled compounds of the compound of formula (I), or their optical isomers, geometric isomers, tautomers or isomer mixtures, or their pesticide-acceptable salts.

[0116] The compound of formula (I) of the present invention can be prepared by the following method:

[0117] The remaining substituents are as described above.

[0118] The specific steps include: dissolving raw material A in a suitable solvent, adding the corresponding acyl compound B, substituting under alkaline conditions, reacting at a temperature of 0-120° C. for 1-24 hours to obtain the target compound I.

[0119] In addition, the present invention also lists a number of exemplary compounds that have been synthesized, and their specific group selections are shown in Table 1 below. It should be understood that the scope of the present invention is not limited to the exemplary compounds listed in the table below, and the various group selections of the compounds in Table 1 below can be arbitrarily combined without particular limitation.

[0120] Table 1 Structures of some compounds

[0121] Table 2 Physical properties and characterization data of some compounds DETAILED DESCRIPTION

[0122] The compounds of formula (I) of the present invention can be synthesized using a variety of methods familiar to those skilled in the art of organic synthesis. The following specific examples provide some exemplary methods for synthesizing compounds of formula (I), which are well known in the field of synthetic chemistry. Obviously, by referring to the exemplary schemes in this patent, those skilled in the art can easily design other synthetic routes for compounds of formula (I) by appropriately adjusting the reactants, reaction conditions, and protecting groups.

[0123] The present invention is further illustrated below with reference to examples; however, these examples are not intended to limit the scope of the present invention. Unless otherwise stated, all reactants used in the examples were obtained from commercial sources; and the instruments and equipment used in the synthesis experiments and product analysis and testing were conventional instruments and equipment commonly used in organic synthesis.

[0124] Example 1: Synthesis of Compound 119

[0125] 2-Chloro-N-cyclopropyl-5-(1-(2,6-dichloro-4-(perfluoropropan-2-yl)phenyl)-1H-pyrazol-4-yl)nicotinamide (0.57 g, 1 mmol) and 30 ml of THF were placed in a 100 ml reaction flask. 60% NaH (0.06 g, 1.5 mmol) was added portionwise with stirring under an ice bath. The reaction was allowed to react at 0°C for 30 min, followed by the slow addition of cyclopropanecarbonyl chloride (0.16 g, 1.5 mmol). After completion, the temperature was raised to 40-50°C and the reaction was stirred overnight. The reaction was terminated after 12 h, cooled to room temperature, quenched with water, and extracted twice with 20 ml of ethyl acetate. The organic phases were combined, washed sequentially with water and saturated brine, dried over sodium sulfate, filtered, evaporated under reduced pressure, and purified by flash column chromatography (petroleum ether / ethyl acetate (v / v) = 5 / 1). The product was obtained as a white solid (0.48 g, yield: 76%).

[0126] 1 H NMR(400MHz,Chloroform-d)δ8.59(d,J=2.4Hz,1H),8.12(s,1H),7.90(s,1H),7.80(d,J=2.4Hz,1H),7.74(s,2H),3.01(dt,J=6.9,3.2Hz, 1H), 2.48 (ddd, J=7.7, 5.2, 3.0Hz, 1H), 1.23 (d, J=6.9Hz, 2H), 1.10 (dt, J=5.5, 3.0Hz, 2H), 1.06 (dt, J=7.8, 2.7Hz, 2H), 1.01–0.93 (m, 2H).

[0127] 19 F NMR(377MHz, CDCl3)δ-75.21,-181.58.

[0128] LC-MS: (M+1) m / z=643.1.

[0129] Other compounds in Table 1 can be prepared by methods similar to those exemplified above.

[0130] Example 2: Bioassay Example

[0131] This example tests the insecticidal activity of some compounds against Plutella xylostella, Spodoptera frugiperda, Spodoptera litura, Spodoptera exigua, Armyworm, Chilo suppressalis, Cutworm, Cat flea, Boophilus microplus, Rhipicephalus sanguineus, Bradygia leekis, Aedes albopictus, and American cockroach.

[0132] The specific implementation process is as follows:

[0133] 1) Compound preparation: A certain mass of the original drug was weighed using an analytical balance (0.0001 g), dissolved in N,N-dimethylformamide containing 1‰ Tween-80 emulsifier to prepare a 1% stock solution, and then diluted with distilled water for later use.

[0134] 2) Test methods

[0135] 2.1 Determination of activity against Plutella xylostella

[0136] Leaf Dip Method: Thoroughly soak an appropriate amount of radish or corn leaves in the prepared solution for 30 seconds, then place in a plastic Petri dish lined with filter paper and allow to air dry in the shade. Eight 2- to 3-year-old diamondback moths are seeded per dish and placed in an observation room at 22°C (16 / 8h). Observe after 48 hours. Gently touch the insects with a brush; insects without a reaction are considered dead. Repeat three times for each treatment, and include a solvent control. The test concentration is 50 mg / L.

[0137] Among some of the tested compounds, compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 263, 268, 275, 289, 293, 306, 321, 331, 333, 345 and 351 showed significant control effects against Plutella xylostella at a concentration of 50 mg / L, with a mortality rate of 100%.

[0138] 2.2 Determination of activity against Spodoptera frugiperda

[0139] Leaf Dip Method: Thoroughly soak an appropriate amount of radish or corn leaves in the prepared solution for 30 seconds, then place in a plastic Petri dish lined with filter paper and allow to air dry in the shade. Eight 2-3rd instar Spodoptera frugiperdae (Spodoptera frugiperdae) are seeded into each dish and placed in an observation room at 22°C (16 / 8h). Observe after 48 hours. Gently touch the insects with a brush; no reaction is considered dead. Repeat three times for each treatment, including a solvent control. The test concentration is 100 mg / L.

[0140] Among some of the tested compounds, compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 263, 268, 275, 289, 293, 306, 321, 331, 333, 345 and 351 showed significant control effects against fall armyworm at a concentration of 100 mg / L, with a mortality rate of 100%.

[0141] 2.3 Determination of activity against Spodoptera litura

[0142] Artificial feed film method: Pour the prepared artificial feed into a 12-well plate while it is still hot, add 2.5 ml of artificial feed to each well, and wait for the feed to cool thoroughly before use. Make three 12-well plates for each concentration gradient of each agent, with each 12-well plate as one replicate, for a total of three replicates. Add 50 μL of the corresponding concentration gradient agent to each well and let it dry. Inoculate one Spodoptera litura larva into each well. For control, add 3 12-well plates, for a total of three replicates, and add 50 μL of solvent control to each well. Place the insects in an insect breeding room with a temperature of 26±2°C, a light intensity of 16h:8h (L:D), and a humidity of 50=70%. Investigate the death of the test insects 48 hours after the test and calculate the mortality rate of the test insects. The test concentrations were 100 mg / L respectively.

[0143] Among some of the tested compounds, compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 263, 268, 275, 289, 293, 306, 321, 331, 333, 345 and 351 showed significant control effects against Spodoptera litura at a concentration of 100 mg / L, with a mortality rate of 100%.

[0144] 2.4 Determination of activity against armyworms

[0145] Potted culture method: Armyworms were reared on an artificial diet, and third-instar larvae were selected as the test insect targets. Wheat was first sprayed using a constant-pressure sprayer. Each treatment was replicated twice, with one pot of wheat seedlings per replicate. Each pot was sprayed with 2.5 ml of the solution. A water control was used as a control. After the solution dried, each pot of wheat seedlings was inoculated with 10 third-instar armyworm larvae. The wheat seedlings were placed in a plastic seedling cup, which was then turned upside down and sealed with double-sided tape. The upper plastic cup was pierced with approximately 10 ventilation holes using pointed tweezers. The seedlings were then placed in an insectary at 24±2°C, with a photoperiod of 16h:8h and a relative humidity of 50%-70%. After 48 hours, the number of targets killed in each treatment was counted and the mortality rate was calculated. The test concentration was 50 mg / L.

[0146] Among some of the tested compounds, compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 263, 268, 275, 289, 293, 306, 321, 331, 333, 345 and 351 showed significant control effects against armyworm at a concentration of 50 mg / L, with a mortality rate of 100%.

[0147] 2.5 Determination of activity against Chilo suppressalis

[0148] Leaf dip method: Select rice seedlings approximately 25 cm tall, grown for three weeks in 5 cm diameter pots, with approximately 30 plants per pot. Remove old and dead leaves and pour a small amount of agar onto the topsoil of the pots to stabilize the soil. Allow the agar to solidify before use. Dip the seedlings in the solution for 10 seconds, then remove and air dry until no visible water is visible. Cut the stems at the base, remove the upper leaves, and leave 5.5-6 cm of stem. Place the seedlings in a 6.5 cm diameter Petri dish. Pad the bottom of each dish with four layers of filter paper and add 3 mL of sterile water to keep them moist. Place 15 stems per dish. Use a brush to pick out 10 mid-second-instar larvae of the Chilo suppressalis (C. suppressalis) and cover the dish with two layers of black cotton cloth before closing the dish to prevent escape. Each experiment consists of 5-6 treatments, with three replicates per treatment. The treated larvae were placed in an incubator at 25°C, 70% relative humidity, and a photoperiod of 16:8 light intensity. After 48 hours, the larvae were examined for mortality. Death was defined as inability to coordinate movement when gently touched with a brush. The test concentrations were 100 mg / L.

[0149] Among some of the tested compounds, compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 275, 263, 268, 289, 293, 306, 321, 331, 333, 345 and 351 showed significant control effects against Chilo suppressalis at a concentration of 100 mg / L, with a mortality rate of 100%.

[0150] 2.6 Determination of activity against cutworms

[0151] Artificial feed film method: Pour the prepared artificial feed for cutworms into a 12-well plate while it is still hot, add 3 ml of artificial feed to each well, and wait until the feed is completely cooled before use. For each concentration of each agent, make three 12-well plates, with each 12-well plate as one replicate, for a total of three replicates, and add 50 μL of the corresponding concentration gradient agent to each well. For the control, make one 12-well plate as one replicate, for a total of three replicates, and add 50 μL of solvent control to each well. All 12-well plates treated in the experiment should be dried and used. Inoculate one 3rd-instar cutworm larva into each well. Place the larva in an insectary at 26±2°C, a light intensity of 16h:8h (L:D), and a humidity of 50-70%. Investigate the mortality of the test insects 72 hours after the experiment and calculate the mortality rate of the test insects. The test concentration is 20 mg / L.

[0152] Among some of the tested compounds, compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 275, 263, 268, 289, 293, 306, 321, 331, 333, 345 and 351 showed significant control effects against black cutworms at a concentration of 20 mg / L, with a mortality rate of more than 90%.

[0153] 2.7 Insecticidal test against cat fleas

[0154] 4 mg of the test compound was dissolved in 40 mL of acetone to obtain a 100 mg / L acetone solution. 400 μL of the solution was applied to the bottom and sides of a 5.3 cm inner diameter culture dish. After the acetone evaporated, a thin film of the compound of the present invention was formed on the inner wall of the culture dish. The inner wall of the culture dish used was 40 cm. 2 , the treatment dose is 1μg / cm 2Ten adult cat fleas (mixed males and females) were placed in the test tubes, covered, and stored in a constant temperature chamber at 25°C. Each treatment was repeated three times. Mortality was observed 72 hours after the test, and the mortality rate was calculated. The test concentration was 100 mg / L.

[0155] Test results: Compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 275, 263, 268, 289, 293, 306, 321, 331, 333, 345 and 351 showed significant efficacy against cat fleas at a concentration of 100 mg / L, showing a mortality rate of more than 75%.

[0156] 2.8 Insecticidal test against Boophilus microplus

[0157] 4 mg of the test compound was dissolved in 40 mL of acetone to obtain a 100 mg / L acetone solution. 400 μL of the solution was applied to the bottom and side surfaces of two culture dishes with an inner diameter of 5.3 cm. After the acetone evaporated, a thin film of the compound of the present invention was formed on the inner wall of the culture dish. The inner wall of the culture dish used was 40 cm. 2 , the treatment dose is 1μg / cm 2 Ten first-stage nymphs of the microtic tick (mixed males and females) were placed in two culture dishes, the joints sealed with tape to prevent escape, and stored in a constant-temperature chamber at 25°C. Each treatment was repeated three times. Mortality was observed 72 hours after the test, and the mortality rate was calculated. The test concentration was 100 mg / L.

[0158] Test results: Among some of the tested compounds, compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 275, 263, 268, 289, 293, 306, 321, 331, 333, 345 and 351 showed significant efficacy against Boophilus microplus at a concentration of 100 mg / L, showing a mortality rate of more than 80%.

[0159] 2.9 Insecticidal test against Rhipicephalus sanguineus

[0160] The collected nymphs of Rhipicephalus sanguinosa were divided into groups, with 10 nymphs in each group and 3 replicates in each group. Two control groups were also set up. Each group of ticks was immersed in different drugs for 5 minutes using an in vitro immersion method. The drug solution on the surface of the ticks was then blotted dry with filter paper, placed in a test tube, sealed with a cloth, and incubated in a 25-28°C incubator. The two control groups were treated with solvents and untreated nymphs that were full of blood as controls, and the other processes were the same as the experimental groups. Statistics on the tick-killing effect: The number of molting nymphs in each group was mainly recorded. Ticks that were able to molt and develop to the adult tick stage were considered to have successfully molted (the fewer the number of molting ticks, the better the effect of the drug in killing ticks). The test concentration was 50 mg / L.

[0161] Test results: Among some of the tested compounds, compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 275, 263, 268, 289, 293, 306, 321, 331, 333, 345 and 351 had significant protective effects against Rhipicephalus sanguinosa at a concentration of 50 mg / L, with a mortality rate of more than 80%.

[0162] 2.10 Insecticidal test on Bradysia chinensis

[0163] Lay clean filter paper flat on an 8cm diameter Petri dish with agar underneath. Add 1mL of the prepared solution to the filter paper. Cut the pseudostem of leek into approximately 2cm segments and soak them in 50mg / L and 5mg / L solutions for 30 seconds, respectively. Remove and remove excess solution with absorbent paper. Place the segments on filter paper dripping with the same concentration of solution, five segments per Petri dish. Then, use a brush to select uniformly sized third-instar Bradysphaeria leek fungus gnat larvae and place them in the Petri dishes, 30 per dish, three replicates, and a blank control. After 48 hours, assess the results. Gently touch the insect body with the brush; no reaction is considered dead. The test concentration is 20mg / L.

[0164] Test results: Among some of the tested compounds, compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 275, 263, 268, 289, 293, 306, 321, 331, 333, 345 and 351 had significant control effects on the leek late-eye fungus gnat at a concentration of 20 mg / L, with a mortality rate of more than 95%.

[0165] 2.11 Insecticidal test against Aedes albopictus

[0166] Aedes albopictus mosquitoes were a susceptible strain imported from the Centers for Disease Control and Prevention and naive to any insecticide exposure. They were reared in a sanitary pest control room. Rearing conditions included a temperature of 26±1°C, a relative humidity of 65%±10%, and a photoperiod of 12h / 12h. For the larval toxicity test, healthy, uniformly sized fourth-instar larvae were selected. The toxicity of the test samples against Aedes albopictus larvae was determined using the standard immersion method according to the WHO (1981). The test concentration was 20 mg / L.

[0167] Test results: Among some of the tested compounds, compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 275, 263, 268, 289, 293, 306, 321, 331, 333, 345 and 351 had significant control effects on the leek late-eye fungus gnat at a concentration of 20 mg / L, with a mortality rate of more than 75%.

[0168] 2.12 Insecticidal test against American cockroaches

[0169] American cockroaches (Periplaneta americana) were a sensitive strain imported from the Centers for Disease Control and Prevention. They were reared in an insectary according to national standards. Rearing conditions included a temperature of 25-27°C, a relative humidity of 60-70%, and darkness except during handling. Healthy, uniformly distributed, fourth-instar male nymphs were used for testing (Scheffler and Dombrowski 1992). The abdominal drip method was used for testing, with mortality criterion being no reaction to the needle. The test concentration was 200 mg / L.

[0170] Test results: Among some of the tested compounds, compounds 3, 9, 26, 31, 35, 39, 58, 76, 81, 86, 90, 93, 98, 102, 107, 111, 115, 119, 146, 172, 178, 189, 195, 199, 204, 209, 214, 219, 224, 228, 232, 237, 247, 258, 275, 263, 268, 289, 293, 306, 321, 331, 333, 345 and 351 showed significant protective effects against American cockroaches at a concentration of 200 mg / L, with the mortality rate being more than 50%.

[0171] 2.13 Comparative Test: CN108137509A discloses an insecticide compound MC1 having a similar substitution structure. Some compounds of the general formula I of the present invention were selected for the experiment and compared with MC1. The results are as follows:

[0172] Table 3 The mortality rate of the compounds of the present invention to diamondback moth at different dosages

[0173] Test results show that the compounds of the present invention have a high mortality rate against Plutella xylostella, Spodoptera frugiperda, Spodoptera litura, Spodoptera exigua, Mythimna armyworm, Chilo suppressalis, Cutworm, Cat flea, Boophilus microplus, Rhipicephalus sanguineus, Bradygia spp., Aedes albopictus, and American cockroaches at different dosages and using different test methods. Other compounds of formula I obtained by the preparation process described above also have the above-mentioned corresponding properties, achieving unexpected results. It is foreseeable that even if the compound dosage is further reduced, the compounds of the present invention will still have outstanding control effects and have excellent development prospects.

[0174] In addition to pest control properties, the compounds according to the present invention unexpectedly show improved degradation properties compared to prior art compounds. In addition, the compounds according to the present invention unexpectedly show lower toxicity to bees (or aquatic animals) and are safe for mammals compared to prior art compounds.

[0175] The above embodiments are preferred implementations of the present invention, but the implementations of the present invention are not limited to the above embodiments. Any other changes, modifications, substitutions, combinations, and simplifications that do not deviate from the spirit and principles of the present invention should be considered equivalent replacement methods and are included in the scope of protection of the present invention.

[0176] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. A compound of formula (I) or an isotope-labeled compound thereof, or an optical isomer, geometric isomer, tautomer or isomer mixture thereof, or an acceptable salt thereof, which is an N-substituted phenylpyrazole derivative. in, X1, X2, X3, and X4 are each independently selected from hydrogen, halogen, hydroxy, nitro, amino, cyano, carboxyl, C 1-6 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, C 1-6 Haloalkyl, C 1-6 Alkoxy or C 1-6 Haloalkoxy; R1 is selected from hydrogen, halogen, hydroxy, cyano, nitro, amino, carboxyl, C 1-6 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, C 1-6 Haloalkyl, C 2-6 Halogenated alkenyl, C 2-6 Haloalkynyl, C 6-10 Aryl, C 6-10 Halogenated aryl, C 6-10 Aryl-C 1-6 Alkyl or C 6-10 Halogenated Aryl-C 1-6 alkyl; R2 is selected from hydrogen, C 1-6 Alkyl, C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-12 Cycloalkyl, C 3-6 Heterocyclic group, C 6-10 Aryl, C 5-12 Heteroaryl, C 1-6 Alkoxy C 1-6 Alkyl, C 3-12 Cycloalkyl C 1-6 Alkyl, and may be substituted or polysubstituted by one or more identical or different substituents selected from: halogen, cyano, C 1-6 Alkyl, C 1-6 Haloalkyl; Q is selected from C 1-6 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-12 Cycloalkyl, C 3-6 Heterocyclic group, C 6-10 Aryl, C 5-12 Heteroaryl, C 1-6 Alkoxy C 1-6 Alkyl, C 1-6 Alkylthio C 1-6 Alkyl, C 3-12 Cycloalkyl C 1-6 Alkyl, C 3-6 Heterocyclyl C 1-6 Alkyl, C 6-10 Aryl C 1-6 Alkyl, C 5-12 Heteroaryl C 1-6 Alkyl, C 6-10 Aryloxy C 1-6 Alkyl, C 5-12 Heteroaryloxy C 1-6 Alkyl, and may be substituted or polysubstituted by one or more identical or different substituents selected from: halogen, cyano, nitro, C 1-6 Alkyl, C 1-6 Alkoxy, C 1-6 Haloalkyl, C 1-6 Alkoxycarbonyl, C 1-3 Alkylamino, C 6-10 Aryl.

2. The compound of formula (I) according to claim 1 or its isotope-labeled compound, or its optical isomer, geometric isomer, tautomer or isomer mixture, or its acceptable salt, wherein: X1, X2, X3, and X4 are each independently selected from hydrogen, halogen, hydroxy, nitro, amino, cyano, carboxyl, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 1-4 Haloalkyl, C 1-4 Alkoxy or C 1-4 Haloalkoxy; R1 is selected from hydrogen, halogen, hydroxy, cyano, nitro, amino, carboxyl, C 1-4 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 1-4 Haloalkyl, C 2-4 Halogenated alkenyl, C 2-4 Haloalkynyl, C 6-10 Aryl, C 6-10 Halogenated aryl, C 6-10 Aryl-C 1-3 Alkyl or C 6-10 Halogenated Aryl-C 1-3 alkyl; R2 is selected from hydrogen, C 1-3 Alkyl, C 1-3 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-12 Cycloalkyl, C 3-6 Heterocyclic group, aryl group, C 5-12 Heteroaryl, C 1-3 Alkoxy C 1-3 Alkyl, C 3-12 Cycloalkyl C 1-3 Alkyl, and may be substituted or polysubstituted by one or more identical or different substituents, the substituents being selected from the group consisting of fluorine, chlorine, bromine, cyano, C 1-3 Alkyl, C 1-3 Haloalkyl; Q is selected from C 1-6 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-12 Cycloalkyl, C 3-6 Heterocyclic group, C 6-10 Aryl, C 5-12 Heteroaryl, C 1-3 Alkoxy C 1-3 Alkyl, C 1-3 Alkylthio C 1-3 Alkyl, C 3-12 Cycloalkyl C 1-3 Alkyl, C 3-6 Heterocyclyl C 1-3 Alkyl, C 6-10 Aryl C 1-3 alkyl, C 5-12 Heteroaryl C 1-3 Alkyl, C 6-10 Aryloxy C 1-3 Alkyl, C 5-12 Heteroaryloxy C 1-3 Alkyl, and may be substituted or polysubstituted by one or more identical or different substituents, the substituents being selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, C 1-3 Alkyl, C 1-3 Alkoxy, C 1-3 Haloalkyl, C 1-3 Alkoxycarbonyl, C 1-3 Alkylamino, C 6-10 Aryl.

3. The compound of formula (I) according to claim 1 or its isotope-labeled compound, or its optical isomer, geometric isomer, tautomer or isomer mixture, or its acceptable salt, wherein: X1, X2, X3, and X4 are each independently selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, amino, carboxyl, C 1-4 Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy or C 1-4 Haloalkoxy; R1 is selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, amino, carboxyl, C 1-4 Alkyl or C 1-4 Haloalkyl; R2 is selected from hydrogen, C 1-3 Alkyl, C 1-3 Alkoxy, C 3-6 Cycloalkyl, C 3-6 Heterocyclic group, C 1-3 Alkoxy C 1-3 Alkyl, C 3-6 Cycloalkyl C 1-3 Alkyl, and may be substituted or polysubstituted by one or more identical or different substituents, the substituents being selected from the group consisting of fluorine, chlorine, bromine, cyano, C 1-3 Alkyl, C 1-3 Haloalkyl; Q is selected from C 1-6 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 3-6 Heterocyclic group, C 6-10 Aryl, C 5-12 Heteroaryl, C 1-3 Alkoxy C 1-3 Alkyl, C 1-3 Alkylthio C 1-3 Alkyl, C 3-6 Cycloalkyl C 1-3 Alkyl, C 3-6 Heterocyclyl C 1-3 Alkyl, C 6-10 Aryl C 1-3 Alkyl, C 5-12 Heteroaryl C 1-3 Alkyl, and may be mono- or poly-substituted by one or more identical or different substituents selected from: Fluorine, chlorine, bromine, cyano, nitro, C 1-3 Alkyl, C 1-3 Alkoxy, C 1-3 Haloalkyl, C 1-3 Alkoxycarbonyl, C 1-3 Alkylamino.

4. The compound of formula (I) according to claim 1 or its isotope-labeled compound, or its optical isomer, geometric isomer, tautomer or isomer mixture, or its acceptable salt, wherein: X1, X2, X3, X4 are each independently selected from hydrogen, fluorine, chlorine, bromine, iodine, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -C(CH3)3, -CH2Cl, -CHF2, -CF 3、 -CH(CF3)2, -CF(CH3)2, -C(CF3)3, -CH2F, -CF2CH3, -CF(CF3)2, -C(OH)(CF3)2, -C(OCH3)(CF3)2; R1 is selected from hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, nitro, amino, carboxyl, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -C(CH3)3, -CH2Cl, -CHF2, -CF3; R2 is selected from hydrogen, C 1-3 Alkyl, C 1-3 Alkoxy, C 3-6 Cycloalkyl, C 1-3 Alkoxy C 1-3 Alkyl, C 3-6 Cycloalkyl C 1-3 Alkyl, and may be substituted or polysubstituted by one or more identical or different substituents, the substituents being selected from the group consisting of fluorine, chlorine, bromine, cyano, C 1-3 Alkyl, C 1-3 Haloalkyl; Q is selected from C 1-6 Alkyl, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-6 Cycloalkyl, C 1-3 Alkoxy C 1-3 Alkyl, C 1-3 Alkylthio C 1-3 Alkyl, C 3-6 Cycloalkyl C 1-3 Alkyl or the following groups, And it may be singly or polysubstituted by one or more identical or different substituents, and the substituents are selected from: fluorine, chlorine, bromine, cyano, nitro, -CH3, -CH2CH3, -CHF2, -CF3, -OCH3, -OCH2CH3, -OCF3, -NHCH3, -N(CH3)2.

5. The compound of formula (I) according to claim 1 or its isotope-labeled compound, or its optical isomer, geometric isomer, tautomer or isomer mixture, or its acceptable salt, which has the following structure:

6. An insecticide composition comprising a compound of formula (I) according to any one of claims 1 to 5 or an isotope-labeled compound thereof, or an optical isomer, geometric isomer, tautomer or isomer mixture thereof, or an acceptable salt thereof, and an acceptable carrier.

7. The insecticide composition according to claim 6, wherein the dosage form is selected from powders, granules, liquids, suspensions, sprays or poison baits, preferably wettable powders, wettable liquids, soluble powders, dispersible liquids, aqueous solutions, microemulsions, emulsifiable concentrates, aqueous emulsions, sprayable solutions, dispersible oil suspensions, microcapsule suspensions, water-dispersible granules, water-soluble granules, large granules, granules for broadcasting and soil application, aerosols, ultra-low volume agents and wax products.

8. Use of the compound of formula (I) or its isotope-labeled compound according to any one of claims 1 to 5, or its optical isomer, geometric isomer, tautomer or isomer mixture, or its pesticide-acceptable salt or the composition according to claim 6 as a pest control agent.

9. The use according to claim 8, wherein the pest is selected from the group consisting of pests belonging to the phylum Arthropoda, the order Coleoptera, the order Diptera, the order Heteroptera, the order Homoptera, the order Hymenoptera, the order Isoptera, the order Lepidoptera, the order Orthoptera, the order Acari, the order Siphonaptera, the order Acarina, the order Blattaria, the order Thysanoptera, and the phylum Nematoda.

10. The use according to claim 9, wherein the pest is selected from the group consisting of Plutella xylostella, Spodoptera: fall armyworm, armyworm, Spodoptera: beet armyworm, Chilo suppressalis, black cutworm, cat flea, Boophilus microplus, Rhipicephalus sanguineus, Bradypodidae, Aedes albopictus, and American cockroach.

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