Isoxazoline substituted benzamide compound and use thereof

Abstract

The present invention belongs to the technical field of pesticides, and specifically relates to an isoxazoline substituted benzamide compound, a stereoisomer and an agriculturally or veterinarily acceptable salt thereof and the use thereof. The compound is as shown in general formula (I), wherein X is halogen; Y is hydrogen or halogen; Z is hydrogen, halogen, cyano, alkyl, alkoxy, alkylthio, etc.; M is CH, CF or N; Q is hydrogen or halogen; R1 is hydrogen, halogen, hydroxyl, cyano, etc.; and R2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, etc. The compound has an excellent control effect on pests.

Description

An isoxazoline-substituted benzamide compound and its application Technical Field

[0001] The invention belongs to the technical field of pesticides, and particularly relates to an isoxazoline-substituted benzamide compound and application thereof. Background Art

[0002] In recent years, due to the long-term use of pest control agents, such as insecticides or fungicides, pests and diseases have acquired drug resistance, making it difficult to control them with existing insecticides or fungicides. In addition, some known pest control agents are highly toxic, or some damage ecosystems through their long-term residual properties. In this situation, despite the existence of a large number of known pesticides, such as WO2015 / 128358, which discloses oxazoline compounds and their use as pesticides, there is still a need to develop new pest control agents with low toxicity and low residual properties. Summary of the Invention

[0003] In order to solve the above-mentioned problems existing in the prior art, the present invention provides an isoxazoline-substituted benzamide compound, its stereoisomers and agriculturally or veterinarily usable salts, which have excellent control effects on pests such as fall armyworm, peach aphid, brown planthopper, truncate spider mite, and leek fungus gnat.

[0004] The technical solution adopted in the present invention is as follows:

[0005] An isoxazoline-substituted benzamide compound as shown in formula I, its stereoisomers and agriculturally or veterinarily acceptable salts:

[0006] wherein X is a halogen;

[0007] Y is hydrogen or halogen;

[0008] Z is hydrogen, halogen, cyano, alkyl, alkoxy, alkylthio or alkylsulfonyl;

[0009] M is CH, CF or N;

[0010] Q is hydrogen or halogen;

[0011] R1 is hydrogen, halogen, hydroxy, cyano, amino, nitro, formyl, cyanoalkyl, hydroxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkylamino, haloalkoxy, haloalkylthio, alkylcarbonyl, alkoxycarbonyl, alkoxyalkyl, haloalkoxyalkyl, alkylaminoalkyl, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally substituted with halogen, -OR 11 、-SR 11 、-(CO)OR 11、-(CO)N(R 11 )2、-(SO2)R 11 or -N(R 11 ) 2, wherein the "cycloalkyl", "cycloalkylalkyl", "aryl", "heterocyclyl", "arylalkyl" or "heterocyclylalkyl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-alkylene-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0012] R2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclic, aryl, Wherein, the "alkyl", "alkenyl" or "alkynyl" is optionally selected from halogen, cyano, nitro, cycloalkyl, trialkylsilyl, cycloalkenyl, heterocyclic, aryl, wherein the “cycloalkyl”, “cycloalkenyl”, “heterocyclyl” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-alkylene-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0013] X 11 Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl or arylalkyl, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11or -N(R 11 )2, wherein the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" or "arylalkyl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-alkylene-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0014] X 13 、X 14 Each independently represents hydrogen, halogen, cyano, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or a group CX 13 X 14 Together they form an unsubstituted or substituted ring structure, or the group NX 13 X 14 Together they form an unsubstituted or substituted heterocyclic group with a nitrogen atom at the 1-position, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 or -N(R 11 )2, wherein the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "heterocyclyl" or "heterocyclylalkyl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-alkylene-(CO)OR 11or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0015] R 11 Each independently represents hydrogen, alkyl, haloalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

[0016] In one embodiment, Z is hydrogen, halogen, cyano, C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio or C1-C8 alkylsulfonyl;

[0017] R1 is hydrogen, halogen, hydroxy, cyano, amino, nitro, formyl, cyano C1-C8 alkyl, hydroxy C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, halo C1-C8 alkoxy, halo C1-C8 alkylthio, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxyC1-C8 alkyl, halogenated C1-C8 alkoxyC1-C8 alkyl, C1-C8 alkylaminoC1-C8 alkyl, aryl, heterocyclic, arylC1-C8 alkyl or heterocyclicC1-C8 alkyl, wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(CO)N(R 11 )2、-(SO2)R 11 or -N(R 11 )2, the "C3-C8 cycloalkyl", "C3-C8 cycloalkylC1-C8 alkyl", "aryl", "heterocyclyl", "arylC1-C8 alkyl" or "heterocyclylC1-C8 alkyl" is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C8 alkylene)-(CO)OR11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0018] R2 is hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, Wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally selected from halogen, cyano, nitro, C3-C8 cycloalkyl, tri-C1-C8 alkylsilyl, cycloalkenyl, heterocyclyl, aryl, wherein the “C3-C8 cycloalkyl”, “C3-C8 cycloalkenyl”, “heterocyclyl” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C8 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0019] X 11 Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl or arylC1-C8 alkyl, wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 or -N(R 11)2, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkylC1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenylC1-C8 alkyl”, “heterocyclyl”, “heterocyclylC1-C8 alkyl”, “aryl” or “arylC1-C8 alkyl” is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-substituted C1-C8 alkyl, halo-substituted C2-C8 alkenyl, halo-substituted C2-C8 alkynyl, halo-substituted C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C8 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0020] X 13 、X 14 Each independently represents hydrogen, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxyC1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, aryl, arylC1-C8 alkyl, heterocyclyl or heterocyclylC1-C8 alkyl, or the group CX 13 X 14 Together they form a 5- to 8-membered carbon ring or a heterocyclic ring containing oxygen, sulfur or nitrogen, or the group NX 13 X 14 Formed together Wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 or -N(R 11)2, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkylC1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenylC1-C8 alkyl”, “aryl”, “arylC1-C8 alkyl”, “heterocyclyl” or “heterocyclylC1-C8 alkyl” is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-substituted C1-C8 alkyl, halo-substituted C2-C8 alkenyl, halo-substituted C2-C8 alkynyl, halo-substituted C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C8 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-, the "5- to 8-membered carbon ring or heterocycle containing oxygen, sulfur or nitrogen" is unsubstituted or substituted with at least one group selected from C1-C8 alkyl, C1-C8 alkoxycarbonyl or benzyl, or forms a condensed ring structure with an aryl or heterocyclic group; is unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl;

[0021] R 11 Each independently represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.

[0022] In another embodiment, Z is hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio or C1-C6 alkylsulfonyl;

[0023] R1 is hydrogen, halogen, hydroxy, cyano, amino, nitro, formyl, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy C1-C6 alkyl, halogenated C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl, aryl, heterocyclic, aryl C1-C6 alkyl or heterocyclic C1-C6 alkyl, wherein the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(CO)N(R 11 )2、-(SO2)R 11 or -N(R 11 )2, the "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C6 alkyl", "aryl", "heterocyclyl", "arylC1-C6 alkyl" or "heterocyclylC1-C6 alkyl" is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-substituted C1-C6 alkyl, halo-substituted C2-C6 alkenyl, halo-substituted C2-C6 alkynyl, halo-substituted C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C6 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0024] R2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl, Wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally selected from halogen, cyano, nitro, C3-C6 cycloalkyl, tri-C1-C6 alkylsilyl, cycloalkenyl, heterocyclyl, aryl, wherein the “C3-C6 cycloalkyl”, “C3-C6 cycloalkenyl”, “heterocyclyl” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C6 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0025] X 11 Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl or arylC1-C6 alkyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 or -N(R 11 )2, the "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenylC1-C6 alkyl", "heterocyclyl", "heterocyclylC1-C6 alkyl", "aryl" or "arylC1-C6 alkyl" is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-substituted C1-C6 alkyl, halo-substituted C2-C6 alkenyl, halo-substituted C2-C6 alkynyl, halo-substituted C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C6 alkylene)-(CO)OR 11or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-;

[0026] X 13 、X 14 Each independently represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, aryl, arylC1-C6 alkyl, heterocyclyl or heterocyclylC1-C6 alkyl, or the group CX 13 X 14 Together they form a 5- to 8-membered carbon ring or a heterocyclic ring containing oxygen, sulfur or nitrogen, or the group NX 13 X 14 Together Wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 or -N(R 11 )2, the "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenylC1-C6 alkyl", "aryl", "arylC1-C6 alkyl", "heterocyclyl" or "heterocyclylC1-C6 alkyl" is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-substituted C1-C6 alkyl, halo-substituted C2-C6 alkenyl, halo-substituted C2-C6 alkynyl, halo-substituted C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C6 alkylene)-(CO)OR 11or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-, the "5- to 8-membered carbon ring or heterocycle containing oxygen, sulfur or nitrogen" is unsubstituted or substituted with at least one group selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl or benzyl, or forms a condensed ring structure with an aryl or heterocyclic group; is unsubstituted or substituted by at least one group selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

[0027] R 11 Each independently represents hydrogen, C1-C6 alkyl, halo-substituted C1-C6 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-substituted C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-substituted C1-C6 alkoxy.

[0028] In the definition of the compounds represented by the above general formula and in all the following structural formulas, the technical terms used, whether used alone or in compound words, represent the following substituents: Alkyl groups with more than two carbon atoms can be straight-chain or branched. For example, the compound word "-O-alkylene-(CO)OR 11 " " in which the alkylene group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group is, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl. The term "cycloalkyl" refers to a group consisting of cyclopentyl, cyclohexyl, cyclopentenyl, cyclohex ...

[0029] Unless otherwise specified, the "aryl" mentioned in the present invention includes but is not limited to phenyl, naphthyl, The "heterocyclic group" includes but is not limited to saturated or unsaturated non-aromatic cyclic groups etc., and also include but are not limited to heteroaryl, i.e. an aromatic cyclic group containing, for example, 3 to 6 ring atoms and optionally fused to a benzo ring, wherein 1 to 4 (e.g. 1, 2, 3 or 4) heteroatoms in the ring atoms are selected from oxygen, nitrogen and sulfur, for example

[0030] If a group is substituted by a group, this is understood to mean that the group is substituted by one or more identical or different groups selected from the groups mentioned. Furthermore, identical or different substituent characters contained in identical or different substituents are independently selected and may be identical or different. The same applies to ring systems formed from different atoms and units. At the same time, compounds known to those skilled in the art to be chemically unstable under standard conditions are excluded from the scope of the claims.

[0031] In addition, unless otherwise specified, the term "substituted by at least one group" as used herein refers to being substituted by 1, 2, 3, 4 or 5 groups; groups (including heterocyclic groups, aryl groups, etc.) without a specific connection position can be connected at any position, including the position connected to C or N; if it is substituted, the substituent can also be substituted at any position as long as it complies with the chemical bond connection rules. For example, a heteroaryl group substituted by 1 methyl group Can represent wait.

[0032] The present invention provides an isoxazoline-substituted benzamide compound having a chiral center as shown in Formula I', its stereoisomers and agriculturally or veterinarily acceptable salts:

[0033] Wherein, the substituents Q, X, Y, Z, M, R1, and R2 are as defined above, and R1 is not hydrogen; the carbon atom at position 2 is a chiral center, and based on the content of stereoisomers having R and S configurations at this position, it has a stereochemical purity of 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), further preferably 90-100% (R), and even more preferably 95-100% (R).

[0034] The present invention also provides an isoxazoline-substituted benzamide compound having a chiral center as shown in Formula I", its stereoisomers and agriculturally or veterinarily acceptable salts:

[0035] Wherein, the substituents Q, X, Y, Z, M, R1, and R2 are as defined above, and R1 is not hydrogen;

[0036] Based on the content of stereoisomers having R and S configurations at position 5, it has a stereochemical purity of 60-100% (S), preferably 70-100% (S), more preferably 80-100% (S), further preferably 90-100% (S), and even more preferably 95-100% (S);

[0037] The carbon atom at position 2 is a chiral center. Based on the content of stereoisomers with R and S configurations at this position, it has a stereochemical purity of 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), further preferably 90-100% (R), and even more preferably 95-100% (R).

[0038] Here, "stereochemical purity" refers to the percentage of the amount of the stereoisomer in question to the total amount of stereoisomers having a chiral center.

[0039] In the present invention, the stereochemical configuration at positions 5 and 2 in Formula I' and Formula I" is determined to be predominantly (5S) and (2R), respectively, according to the Cahn-Ingold-Prelog system. However, the subject matter of the present invention also relates to all stereoisomers at other positions encompassed by Formula I, Formula I' and Formula I", and mixtures thereof. Such compounds of Formula I, Formula I' and Formula I" may contain, for example, one or more additional asymmetric carbon atoms or other double bonds not specifically described in Formula I, Formula I' and Formula I". It should be understood that the present invention includes pure isomers and mixtures thereof enriched to varying degrees in pure isomers, wherein the asymmetric carbon atom at the marked position 5 is in the S-configuration and / or the asymmetric carbon atom at the marked position 2 is in the R-configuration, or in mixtures in which compounds or compounds of the same chemical structure have the configurations at the marked positions, or are present in a proportion in which the compounds having the configurations are predominant (at least 60% of the configurations), while the other asymmetric carbon atoms may be present in racemic form or may be resolved to varying degrees. As long as the stereochemical configuration conditions at the marked positions are met, possible stereoisomers defined by specific spatial forms, such as enantiomers, diastereomers, Z- and E-isomers, are included in Formula I, Formula I' and Formula I", and can be obtained from mixtures of stereoisomers using conventional methods, or can be prepared by stereoselective reactions combined with the use of stereochemically pure starting materials.

[0040] If various functional groups are present, the present invention also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0041] Stereoisomers can be obtained from the mixture obtained in the preparation by optical resolution. Stereoisomers can also be selectively prepared by using stereoselective reactions and optically active starting materials and / or auxiliary agents. For optical resolution, conventional methods (see Textbooks of Stereochemistry) can usually be used, such as the following methods for separating the mixture into diastereomers, such as physical methods, such as crystallization, chromatography, especially column chromatography and high pressure liquid chromatography, optionally distillation methods under reduced pressure, extraction methods and other methods, usually using chromatographic separation on a chiral solid phase, which can separate the residual mixture of enantiomeric structures. Suitable for preparation or for industrial scale is such a method, such as crystallization of diastereomeric salts, which can be obtained from compounds using optically active acids, and if an acidic group is present, optically active bases can be used as needed.

[0042] The salts of the compounds of the formula I, formula I' and formula I" are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary manner, for example by reacting the compounds with acids of the anions mentioned, if the compounds of the formula I, formula I' and formula I" have basic functional groups, or by reacting acidic compounds of the formula I, formula I' and formula I" with suitable bases.

[0043] Suitable agriculturally acceptable salts are in particular salts of those cations or acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the invention. Suitable cations are in particular alkali metal ions, preferably lithium, sodium and potassium ions; alkaline earth metal ions, preferably calcium, magnesium and barium ions; transition metal ions, preferably manganese, copper, zinc and iron ions; and ammonium (NH4 + ) and substituted ammonium in which 1 to 4 hydrogen atoms are replaced by C1-C4 alkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy, C1-C4 alkoxy-C1-C4 alkyl, hydroxy-C1-C4 alkoxy-C1-C4 alkyl, phenyl or benzyl. Examples of substituted ammonium ions include methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, di(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, in addition to phosphonium ions, sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4 alkyl)sulfoxonium.

[0044] Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, hydrogencarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the formula I, formula I' and formula I" with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

[0045] The term "veterinarily acceptable salt" refers to salts of those cations or anions that are known and accepted in the art of veterinary salt formation. Suitable acid addition salts formed, for example, with compounds of Formula I, Formula I' and Formula I" containing a basic nitrogen atom, such as an amino group, include salts with inorganic acids, such as hydrochlorides, sulfates, phosphates and nitrates, and organic acids, such as acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methanesulfenic acid, methanesulfonic acid and succinic acid.

[0046] The compounds of the present invention, including their salts, stereoisomers, and tautomers, are particularly suitable for effectively controlling invertebrate pests. "Invertebrate pests" include arthropods, gastropods, nematodes, and worms that are economically important pests. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, woodlice, and synechids. The term "gastropod" includes snails, slugs, and other stylopods. The term "nematode" includes all members of the class Nematoda. It is particularly suitable for effectively controlling or eliminating the following pests: lepidoptera insects (Lepidoptera), beetles (Coleoptera), flies, mosquitoes (Diptera), thrips (Thysanoptera), termites (Isoptera), cockroaches (Blattaria-Blattodea), bed bugs, aphids, leafhoppers, whiteflies, scales, cicadas (Hemiptera), ants, bees, wasps, sawflies (Hymenoptera), era), crickets, grasshoppers, locusts (Orthoptera), arachnids (Arachnida), fleas (Siphonaptera), silverfish, house silverfish (Thysanura), centipedes (Chilopoda), millipedes (Diplopoda), earwigs (Dermaptera), lice (Phthiraptera), springtails (Collembola), etc. They may infest plants, thereby causing significant damage to the infested plants, and may infect animals, especially warm-blooded animals such as mammals or birds or other higher animals such as reptiles, amphibians or fish, thereby causing significant damage to the infested animals.

[0047] The present invention also relates to a method for preparing the isoxazoline-substituted benzamide compound, its stereoisomers and agriculturally or veterinarily acceptable salts, comprising the following steps:

[0048] The compound represented by general formula II is reacted with the compound represented by general formula III or a salt thereof (such as hydrochloride) in the presence of a condensing agent to obtain a compound represented by general formula I. The chemical reaction equation is as follows:

[0049] wherein P represents OH or halogen, preferably Cl; and the substituents Q, X, Y, Z, M, R1 and R2 are as defined above.

[0050] In a specific embodiment, the condensing agent is PyBOP, HATU, HOBt-EDCI, CDI, DCC or DBU.

[0051] In another embodiment, the reaction is carried out in the presence of a base and a solvent.

[0052] In another specific embodiment, the solvent is selected from one or more of dichloromethane, dichloroethane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, toluene, and xylene.

[0053] In another embodiment, the base is selected from one or more of triethylamine, trimethylamine, DIPEA and NMM.

[0054] In one embodiment, when P is OH, the compound represented by general formula II is prepared by hydrolyzing the compound represented by general formula IV, and the chemical reaction equation is as follows:

[0055] The compound represented by general formula IV is prepared by a cycloaddition reaction of the compound represented by general formula V with hydroxylamine hydrochloride. The chemical reaction equation is as follows:

[0056] Wherein, W represents a C1-C6 alkyl group or a phenyl group.

[0057] In addition, the above-mentioned compound can be prepared by referring to the methods shown in CN111936492A, WO2005 / 085216, etc.

[0058] The present invention also provides an intermediate, as shown in Formula II.

[0059] The present invention also relates to an insecticide composition comprising a biologically effective amount of the isoxazoline-substituted benzamide compound, at least one of its stereoisomers and agriculturally or veterinarily acceptable salts, and preferably, further comprising a formulation adjuvant.

[0060] Such compositions may comprise an individual active compound according to the invention or a mixture of several active compounds according to the invention.The compositions according to the invention may comprise individual isomers or mixtures of isomers or salts as well as individual tautomers or mixtures of tautomers.

[0061] In addition, the composition of the present invention may also include an insecticide or acaricide having an action mechanism classified according to IRAC regulations as an active ingredient, and the combined application has obvious synergistic and synergistic effects.

[0062] Examples of insecticides or acaricides having a mechanism of action classified according to the IRAC regulations include (1A) acetylcholinesterase (AChE) inhibitors (carbamate type), (1B) acetylcholinesterase (AChE) inhibitors (organophosphorus type), (2) GABA-activated chloride ion (chloride) channel blockers, (3A) sodium channel modulators (pyrethroid type), (3B) sodium channel modulators (DDT type), (4) nicotinic acetylcholine receptor (nAChR) competitive modulators, (5) nicotinic acetylcholine receptor (nAChR) allosteric modulators, (6) glutamate-activated chloride ion (chloride) channel (GluCl) allosteric modulators, (7) juvenile hormone analogs, (8) other nonspecific (multi-site) inhibitors, (9) chord organ TRPV channel modulators, (10) mite growth inhibitors, (11) microbial insect midgut lining disruptors, (12) mitochondrial ATP synthase inhibitors, (13) Oxidative phosphorylation uncouplers that disrupt the proton gradient, (14) Nicotinic acetylcholine receptor (nAChR) channel blockers, (15) Chitin biosynthesis inhibitors, type 0, (16) Chitin biosynthesis inhibitors, type 1, (17) Molting inhibitors, (18) Ecdysone (ecdysone) receptor agonists, (19) Octopamine receptor agonists, (20) Mitochondrial electron transport complex III inhibitors, (21) Mitochondrial electron transport complex I inhibitors (METI), (22) Voltage-dependent sodium channel blockers, (23) Acetyl CoA carboxylase inhibitors, (24) Mitochondrial electron transport complex IV inhibitors, (25) Mitochondrial electron transport complex II inhibitors, (28) Rianodine receptor modulators, (29) Chord modulators with unidentified target site, (30) GABA-activated chloride (chloride) channel allosteric modulators, and (UN) agents with unknown or unclear mechanisms of action.

[0063] Specific examples of the above compounds are illustrated below.

[0064] (1A) Acetylcholinesterase (AChE) inhibitors (carbamates)

[0065] Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Fumarate Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, Xylylcarb.

[0066] Aldoxycarb, Allyxycarb, Aminocarb, Bufencarb, Cloethocarb, Fenothiocarb, Promecarb.

[0067] (1B) Acetylcholinesterase (AChE) inhibitors (organophosphates)

[0068] Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isoprophos Isofenphos, Isopropylo-(methoxyaminothio-phosphoryl)salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-m ethyl), Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion,Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon-methyl, Triazophos, Trichlorfon, Vamidothion, Bromophos-ethyl, Cyanofenphos, Demeton-S-methylsulfone, Dialifos ), Dichlofenthion, Dioxabenzofos, Etrimfos, Fensulfothion, Fonofos, Formothion, Iodofenphos, Isazofos, Isocarbofos, Methacrifos, Phosphocarb, Pirimiphos-ethyl, Propaphos, Prothoate, Sulprofos.

[0069] (2) GABA-activated chloride channel blockers

[0070] Chlordane, Endosulfan, Ethiprole, Fipronil, Acetoprole, Camphechlor, Dienochlor, Heptachlor, Pyrafluprole, Pyriprole, and Flufiprole.

[0071] (3A) Sodium channel modulators (pyrethroids)

[0072] Acrinathrin, Allethrin, d-cis-transAllethrin, d-trans-Allethrin, Bifenthrin, Bioallethrin, Bioallethrin S-cyclopentenyl-isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, Beta -Cyhalothrin (beta-Cyfluthrin), Cyhalothrin, lambda-Cyhalothrin, gamma-Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta-Cypermethrin, phenothrin [(1R)-trans isomer

[0073] Cyphenothrin [(1R)-trans-isomers]), Deltamethrin, Empenthrin [(EZ)-(1R)-isomers], Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, tau-Fluvalinate, Bromo Halfenprox, Imiprothrin, Kadethrin, Permethrin, Phenothrin [(1R)-trans-isomer], Prallethrin, Pyrethrins, Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)-isomer] [(1R)-isomers]), Tralomethrin, Transfluthrin, kappa-Bifenthrin, Biopermethrin, Chloroprallethrin, Dimefluthrin, Fenfluthrin, Fenpirithrin, Flufenprox, Heptafluthrin, Meperfluthrin ), epsilon-Metofluthrin, Momfluorothrin, epsilon-Momfluorothrin, trans-Permethrin, Profluthrin, Protrifenbute, kappa-Tefluthrin, Terallethrin, Tetramethylfluthrin, Bioethanomethrin.

[0074] (3B) Sodium channel modulators (DDT class)

[0075] DDT, Methoxychlor.

[0076] (4) Competitive modulators of nicotinic acetylcholine receptors (nAChR)

[0077] Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam, Nicotine, Sulfoxaflor, Flupyradifurone, Triflumezopyrim, Nithiazine, Diclomezotiaz, N-[(E)-1-(6-chloro-3-pyridylmethyl)pyridine-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Flupyrimin).

[0078] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators

[0079] Spinetoram, Spinosad.

[0080] (6) Glutamate-activated chloride ion (chloride) channel (GluCl) allosteric modulator

[0081] Abamectin, Emamectin, Emamectin-benzoate, Lepimectin, Milbemectin, Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin.

[0082] (7) Juvenile hormone analogs

[0083] Hydroprene, Kinoprene, Methoprene; Fenoxycarb; Pyriproxifen, Diofenolan, Epofenonane, Triprene.

[0084] (8) Other nonspecific (multi-site) inhibitors

[0085] Methyl bromide, alkyl halides, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium borate, sodium metaborate, tartar emetic, dazomet, metam, metampotassium, metamsodium.

[0086] (9) String organ TRPV channel modulator

[0087] Pymetrozine, Pyrifluquinazon, Afidopyropen.

[0088] (10) Mite growth inhibitors

[0089] Clofentezine, Diflovidazin, Hexythiazox, Etoxazole.

[0090] (11) Microbial-derived insect midgut lining destroyer

[0091] Bacillus thuringiensis subsp. israelensis, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1, Bacillus sphaericus.

[0092] (12) Mitochondrial ATP synthase inhibitors

[0093] Diafenthiuron, Azocyclotin, Cyhexatin, Fenbutatin-oxide, Propargite; Tetradifon.

[0094] (13) Oxidative phosphorylation uncouplers that disrupt the proton gradient

[0095] Chlorfenapyr, DNOC (4,6-dinitro-o-cresol), Sulfluramid, Binapacryl, Dinobuton, and Dinocap.

[0096] (14) Nicotinic acetylcholine receptor (nAChR) channel blockers

[0097] Bensultap, Cartap hydrochloride, Thiocyclam, Thiosultap-sodium.

[0098] (15) Chitin biosynthesis inhibitors, type 0

[0099] Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Novifluron, Teflubenzuron, Triflumuron, Fluazuron.

[0100] (16) Chitin biosynthesis inhibitors, type 1

[0101] Buprofezin (Buprofezin).

[0102] (17) Molting inhibitors

[0103] Cyromazine.

[0104] (18) Ecdysone (ecdysone) receptor agonists

[0105] Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.

[0106] (19) Octopamine receptor agonists

[0107] Amitraz, Chlordimeform.

[0108] (20) Mitochondrial electron transport complex III inhibitors

[0109] Hydramethylnon, Acequinocyl, Fluacrypyrim, Bifenazate.

[0110] (21) Mitochondrial electron transport complex I inhibitor (METI)

[0111] Fenazaquin, Fenpyroximate, Pyridaben, Pyrimidifen, Tebufenpyrad, Tolfenpyrad, Rotenone.

[0112] (22) Potential-dependent sodium channel blockers

[0113] Indoxacarb, Metaflumizone.

[0114] (23) Acetyl CoA carboxylase inhibitors

[0115] Spirodiclofen, Spiromesifen, Spirotetramat, Spiropyridine ethyl ester.

[0116] (24) Mitochondrial electron transport complex IV inhibitors

[0117] Aluminum phosphide (Al-phosphide), calcium phosphide (Ca-phosphide), phosphine (Phosphine), zinc phosphide (Zn-phosphide); calcium cyanide (Ca-cyanide), sodium cyanide (Na-cyanide), potassium cyanide (K-cyanide).

[0118] (25) Mitochondrial electron transport complex II inhibitors

[0119] Cyenopyrafen, Cyflumetofen, Cyetpyrafen; Pyflubumide.

[0120] (28) Rianodine receptor modulators

[0121] Chlorantraniliprole, Cyantraniliprole, Cyclaniliprole, Flubendiamide, Cyhalodiamide, Tetrachlorantraniliprole, Tetraniliprole.

[0122] (29) The target site of the chord modulator has not been determined

[0123] Flonicamid.

[0124] (30) GABA-activated chloride ion (chloride ion) channel allosteric modulator

[0125] Broflanilide, 4-[(5RS)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-trifluoromethyl-1,2-oxazol-3-yl]-N-[(EZ)-(methoxyimino)methyl]-o-toluamide, Isocycloseram; Afoxolaner, Fluralaner, Lotilaner, Sarolaner.

[0126] (UN) Azadirachtin, Benzoximate, Bromopropylate, Chinomethionat, Dicofol, Limesulfur, Mancozeb, Pyridalyl, Sulfur, Acynonapyr, Amidoflumet, Benzomate, Benzpyrimoxan, Chlorobenzilate, Dicyclanil, fenoxacrim, fentrifanil, flometoquin, flubenzimine, flufenzine, fluhexafon, fluopyram, metoxadiazone, 2-[3-(ethylsulfonyl)-2-pyridinyl]-5-[(trifluoromethyl)sulfonyl]benzoxazole (oxazosulfyl), Tetrasul, triarathene, tyclopyrazoflor, and dimpropyridaz.

[0127] The term "biologically effective amount" refers to an amount of a biologically active compound (e.g., a compound of Formula I, Formula I', and Formula I") that is sufficient to produce the desired biological effect when applied to (i.e., contacted with) the pest to be controlled or its environment, or the plant, the seed from which the plant grows, or the locus of the plant (e.g., the growth medium), thereby protecting the plant from damage by the pest or achieving other desired effects (e.g., increasing plant vigor). The compounds of the present invention can also be applied prophylactically to locations where pests or parasites are expected to appear.

[0128] Compound I, its stereoisomers and salts can be converted into conventional types of agrochemical compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressed articles, capsules and mixtures thereof. Examples of composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressed articles (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticide preparations (e.g. LN) and gel formulations for treating plant propagation materials such as seeds (e.g. GF).

[0129] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, tackifiers and adhesives.

[0130] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling point mineral oil fractions, for example kerosene, diesel; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, for example toluene, paraffin, tetralin, alkylated naphthalenes; alcohols, for example ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example cyclohexanone; esters, for example lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, for example N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[0131] Suitable solid carriers or fillers are mineral earths, for example silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, for example cellulose, starch; fertilizers, for example ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of plant origin, for example cereal flour, bark flour, wood flour and nut shell flour, and mixtures thereof.

[0132] Suitable surfactants are surface-active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids or adjuvants.

[0133] Suitable anionic surfactants are alkali metals, alkaline earth metals or ammonium salts of sulfonic acid, sulfuric acid, phosphoric acid, carboxylic acids and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, α-olefinsulfonates, ligninsulfonates, fatty acids and oily sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalene sulfonates, dodecyl- and tridecylbenzene sulfonates, naphthalene and alkylnaphthalene sulfonates, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oily sulfates, ethoxylated alkylphenol sulfates, sulfates of alcohols, sulfates of ethoxylated alcohols or sulfates of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkylcarboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0134] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated with 1-50 equivalents. Ethylene oxide and / or propylene oxide can be used for the alkoxylation, with ethylene oxide being preferred. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerides or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinyl pyrrolidone, vinyl alcohol or vinyl acetate.

[0135] Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with 1 or 2 hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers comprising blocks of polyoxyethylene and polyoxypropylene, or ABC type block polymers comprising alkanol, polyoxyethylene and polyoxypropylene. Suitable polyelectrolytes are polyacids or polyalkalis. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polyalkalis are polyvinylamine or polyvinylamine.

[0136] Suitable adjuvants are compounds which themselves have negligible or even no pesticidal activity and which improve the biological properties of the compounds I towards the target substances. Examples are surfactants, mineral or vegetable oils and other adjuvants.

[0137] Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[0138] Suitable fungicides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

[0139] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol.

[0140] Suitable defoamers are silicones, long-chain alcohols and fatty acid salts.

[0141] Suitable colorants (for example red, blue or green) are low water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (for example iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (for example alizarin colorants, azo colorants and phthalocyanine colorants).

[0142] Suitable tackifiers or adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, bio- or synthetic waxes and cellulose ethers.

[0143] The present invention also provides a method for controlling pests, which comprises contacting the pests or their environment with a biologically effective amount of the isoxazoline-substituted benzamide compound, its stereoisomers and agriculturally or veterinarily acceptable salts or the composition.

[0144] In one embodiment, the pest, its food supply, its habitat or its breeding ground, or the cultivated plants, plant propagation materials (such as seeds), soil, area, material or environment in which the pest grows or may grow, or the material, cultivated plants, plant propagation materials (such as seeds), soil, surface or space to be protected from infestation or infestation by the pest, is treated with a biologically effective amount of a compound of the invention or a composition as defined above.

[0145] The present invention also relates to the use of the compounds of the present invention, their stereoisomers and / or agriculturally or veterinarily acceptable salts or compositions thereof for controlling pests.

[0146] The term "controlling pests" refers to inhibiting the development of pests (including mortality, reduced feeding, and / or mating disruption), and related expressions may be defined similarly.

[0147] The term "plant propagation material" should be construed as representing all propagation parts of a plant such as seeds, and asexual plant materials such as cuttings and tubers (e.g., potatoes) that can be used for propagating plants. This includes seeds, roots, fruits, tubers, bulbs, underground stems, branches, buds and other plant parts, including rice seedlings and seedlings transplanted by soil after germination or after emergence. Plant propagation material can be treated with plant protection compounds preventatively when or before planting or transplanting. The seedling can also be protected by the complete or partial treatment via dipping or watering before transplanting.

[0148] The term "plants" includes any type of plants, including "non-cultivated plants" and especially "cultivated plants".

[0149] The term "non-cultivated plant" refers to any wild-type variety or related variety or related genus of a cultivated plant.

[0150] The term "cultivated plants" is understood to include plants that have been modified by breeding, mutagenesis or genetic engineering, including but not limited to agricultural biotechnology products that are marketed or in development (see http: / / www.bio.org / speeches / pubs / er / agri_products.asp). Genetically modified plants are plants whose genetic material is not readily obtained by hybridization, mutation or natural recombination under natural conditions. One or more genes are typically integrated into the genetic material of a genetically modified plant to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modifications of proteins, oligopeptides or polypeptides, for example by glycosylation or polymer addition such as prenylated, acetylated or farnesylated moieties or PEG moieties. DETAILED DESCRIPTION

[0151] The following examples are provided to illustrate the present invention and should not be considered to limit the present invention in any way. The scope of the rights claimed in the present invention is described in the claims.

[0152] Given the economical efficiency and diversity of the compounds, we have selected and synthesized a number of compounds. A selection of these compounds is listed in Table 1 below. The specific compound structures and corresponding compound information are shown in Table 1. The compounds in Table 1 are intended to better illustrate the present invention but are not intended to limit the present invention. Those skilled in the art should not interpret this as limiting the scope of the present invention to the following compounds.

[0153] Table 1 Compound structures and their 1 H NMR values

[0154] Table A is constructed in the same manner as Table 1 above, except that the general formula I is replaced by the general formula I′ having a chiral center. (R1 is not H), and in Table A, the entries under the "Serial Number" column heading are sequentially recited as 1(2R)-22(2R), 25(2R)-90(2R). For example, 1(2R) corresponds to a compound in which the 2 position of compound 1 in Table 1 is in the R configuration.

[0155] Table B is constructed identically to Table 1 above, except that the chiral center of formula I is replaced with the chiral center of formula I. (R1 is not H), and in Table B, the entries under the "Serial Number" column heading are sequentially recited as 1(2R,5S)-22(2R,5S), 25(2R,5S)-90(2R,5S). For example, 1(5S,2R) corresponds to a compound in Table 1 in which the 5-position is S-configured and the 2-position is R-configured.

[0156] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The starting materials can be purchased commercially or can be prepared by methods known in the literature or as described in detail. It will be understood by those skilled in the art that other synthetic routes can also be used to synthesize the compounds of the present invention. Although the specific starting materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar starting materials and conditions, and these modifications or variations of the preparation methods of the present invention that result in various isomerizations of the compounds are included within the scope of the present invention. In addition, the preparation methods described below can be further modified according to the present disclosure using conventional chemical methods well known to those skilled in the art. For example, appropriate groups can be protected during the reaction, etc.

[0157] The following process examples are provided to facilitate a further understanding of the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further illustrate the present invention and are not intended to limit its reasonable scope. The reagents used in the synthesis of the compounds shown below are either commercially available or can be readily prepared by one of ordinary skill in the art.

[0158] Examples of representative compounds are shown below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0159] 1. Synthesis of compound 5(2R)

[0160] (1) Add 5-1 (130 mg, 1.5 eq), 5-2 (1 eq), sodium carbonate (3 eq), and 30 ml of acetonitrile to a 100 mL round-bottom flask. React at 100°C overnight. If there is still an undehydrated intermediate in the system, add more acetonitrile and raise the temperature to 110°C to push the intermediate to the product. After the reaction is completed, extract with ethyl acetate and water, add anhydrous sodium sulfate to dry the organic phase, and spin dry to obtain a yellow oil 5-3 (354 mg).

[0161] (2) In a 50 mL round-bottom flask, 5-3 (354 mg, 1.0 eq) and 5 ml of 1,2-dichloroethane were added to the flask. TBAB (0.1 eq) was added. Hydroxylamine hydrochloride (5 eq) and sodium hydroxide (6 eq) were weighed and placed in another flask. Water was added to dissolve the mixture. The mixed aqueous solution of hydroxylamine hydrochloride and sodium hydroxide was added dropwise to the raw material system under an ice bath. The ice bath was naturally warmed to room temperature and the reaction was carried out for 3 h. After the reaction was completed, the mixture was extracted with dichloromethane and water. The organic phase was dried over anhydrous sodium sulfate and purified by column chromatography. The product was obtained with PE:EA = 15%. The product was then dried to obtain 5-4 (450 mg) as a white solid.

[0162] (3) In a 50 mL round-bottom flask, 5-4 (450 mg, 1.0 eq) and 4 mL of solvent (THF:H2O = 3:1) were added, followed by sodium hydroxide (3 eq). The mixture was reacted at 50°C for 1 h. After the reaction, the mixture was extracted with ethyl acetate and dilute hydrochloric acid, and the organic phase was dried over anhydrous sodium sulfate and dried to obtain 5-5 as a yellow oil (296 mg, 67% yield).

[0163] (4) In a 50 mL round-bottom flask, 5-5 (296 mg, 1.0 eq), EDCI (1.5 eq), HOBT (1.5 eq), TEA (3 eq), and 5 ml of dichloromethane were added to the flask. 5-6 (1.5 eq) was then added and allowed to react overnight at room temperature. After the reaction, the mixture was extracted with dichloromethane and water, and the organic phase was dried over anhydrous sodium sulfate. The product was purified by column chromatography with PE:EA = 30% and then dried to obtain 5(2R) as a light yellow oil (60 mg, 84% purity, 17.6% yield).

[0164] 2. Synthesis of compound 21(2R)

[0165] (1) 500 mg of compound 21-1 (1 eq), 21-2 (1.5 eq), and sodium carbonate (1 eq) were added to a single-necked flask, and 15 ml of acetonitrile was added. The mixture was stirred at 100°C and reacted overnight. After the reaction was completed, the sodium carbonate was filtered off, and the mixture was extracted with water and EA. The organic phase was mixed and purified by column to obtain the product 21-3 (300 mg, yield 31%).

[0166] (2) 300 mg of compound 21-3 (1 eq) was added to a single-necked bottle and dissolved in 15 ml of DCE. TBAB (0.05 eq) was added under ice bath. Sodium hydroxide (6 times the volume of water, 5 eq) was added to another single-necked bottle. Hydroxylamine hydrochloride (50% water, 4 eq) was added under ice bath and reacted for 30 min. The hydroxylamine hydrochloride solution was added dropwise to another reaction mixture and reacted for 6 h. The mixture was extracted with DCE, filtered, and dried to obtain crude product 21-4 (300 mg).

[0167] (3) 300 mg of compound 21-4 (1 eq) was dissolved in THF, and an aqueous solution of sodium hydroxide (3 eq) was added dropwise. The mixture was stirred at room temperature overnight. After the reaction was completed, water was added to the reaction solution, and the pH was adjusted to 2-3 with dilute hydrochloric acid. The mixture was extracted with EA, washed once with saturated brine, dried over anhydrous sodium sulfate, and dried to obtain the product 21-5 (288 mg, yield 98%).

[0168] (4) 150 mg of compound 21-5 (1 eq), D-alanine methyl ester hydrochloride (1.2 eq), EDCI (1.5 eq), and HOBT (1.5 eq) were added to a single-necked bottle, dissolved in 15 ml of DCM, and TEA (2 eq) was added and stirred evenly. The mixture was reacted at room temperature for 4 h.

[0169] Column chromatography gave the product 21(2R) (85 mg, yield 48%).

[0170] Biological activity evaluation:

[0171] (1) Insecticidal activity test:

[0172] The compound of the present invention was dissolved in acetone and then diluted with water to form a gradient of drug solutions (ppm). Corn leaves were immersed in the drug solutions of different concentrations for approximately 20 seconds, air-dried, and placed in a petri dish. Three-instar fall armyworms were placed in each dish. Peanut leaves were immersed in the drug solutions of different concentrations for approximately 20 seconds, air-dried, and placed in a petri dish. Truncate spider mites (adult mites) were placed in each dish. Chive pseudostems were immersed in the drug solutions of different concentrations for approximately 20 seconds, air-dried, and placed in a petri dish. Three-instar bradya fungus gnats were placed in each dish. Rice stalks were immersed in the drug solutions of different concentrations for approximately 20 seconds, air-dried, and placed in a petri dish. Three-instar brown planthoppers were placed in each dish. The dishes were covered and stored in a constant temperature chamber at 25°C. Radish leaves infested with peach aphids were cut, immersed in the drug solutions of different concentrations for approximately 5 seconds, air-dried, and placed in a petri dish. The dishes were covered and stored in a constant temperature chamber at 25°C. After 48 hours, the number of dead insects was checked and the mortality rate was calculated according to the formula: mortality rate (%) = (number of dead insects / number of test insects) * 100. In addition, the test was performed in duplicate.

[0173] Table 2 Insecticidal test results Note: N stands for no data; Reference compound A: Control compound B:

[0174] At the same time, after many tests, it was found that many of the compounds and compositions of the present invention have good control activity against agricultural pests such as Lepidoptera (such as corn borer, striped stem borer, diamondback moth, Spodoptera litura, beet armyworm, cotton bollworm, fall armyworm, armyworm, etc.), Homoptera (such as cotton aphid, radish aphid, pea aphid, peanut aphid, green stink bug, etc.), Acarina (such as two-spotted spider mite, truncate spider mite, Turkestan spider mite, etc.), Diptera (such as leek bradgy fungus gnat, etc.), Coleoptera (such as yellow flea beetle, monkey leaf beetle, etc.) and thrips (such as palm thrips, onion thrips, tobacco thrips, etc.), as well as sanitary pests such as cockroaches (such as termites, cockroaches, etc.) and Muscidae (such as flies, mosquitoes, etc.). They not only have the characteristics of broad spectrum, high efficiency, and strong systemic absorption, but can also effectively control resistant pests and have certain commercial value.

Claims

1. An isoxazoline-substituted benzamide compound as shown in Formula I, its stereoisomers and agriculturally or veterinarily acceptable salts: in, X is a halogen; Y is hydrogen or halogen; Z is hydrogen, halogen, cyano, alkyl, alkoxy, alkylthio or alkylsulfonyl; M is CH, CF or N; Q is hydrogen or halogen; R1 is hydrogen, halogen, hydroxy, cyano, amino, nitro, formyl, cyanoalkyl, hydroxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkylamino, haloalkoxy, haloalkylthio, alkylcarbonyl, alkoxycarbonyl, alkoxyalkyl, haloalkoxyalkyl, alkylaminoalkyl, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally substituted with halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(CO)N(R 11 )2、-(SO2)R 11 or -N(R 11 )2, wherein the "cycloalkyl", "cycloalkylalkyl", "aryl", "heterocyclyl", "arylalkyl" or "heterocyclylalkyl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-alkylene-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclic, aryl, Wherein, the "alkyl", "alkenyl" or "alkynyl" is optionally selected from halogen, cyano, nitro, cycloalkyl, trialkylsilyl, cycloalkenyl, heterocyclic, aryl, wherein the "cycloalkyl", "cycloalkenyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-alkylene-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; X 11 Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl or arylalkyl, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 or -N(R 11 )2, wherein the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" or "arylalkyl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-alkylene-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; X 13 、X 14 Each independently represents hydrogen, halogen, cyano, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or a group CX 13 X 14 Together they form an unsubstituted or substituted ring structure, or the group NX 13 X 14 Together they form an unsubstituted or substituted heterocyclic group with a nitrogen atom at the 1-position, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 or -N(R 11 )2, wherein the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "heterocyclyl" or "heterocyclylalkyl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-alkylene-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R 11 Each independently represents hydrogen, alkyl, haloalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

2. The isoxazoline-substituted benzamide compound, its stereoisomers and agriculturally or veterinarily acceptable salts according to claim 1, characterized in that: Z is hydrogen, halogen, cyano, C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio or C1-C8 alkylsulfonyl; R1 is hydrogen, halogen, hydroxy, cyano, amino, nitro, formyl, cyano C1-C8 alkyl, hydroxy C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, halo C1-C8 alkoxy, halo C1-C8 alkylthio, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy C1-C8 alkyl, halo C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylamino C1-C8 alkyl, aryl, heterocyclyl, aryl C1-C8 alkyl or heterocyclyl C1-C8 alkyl, wherein, The "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(CO)N(R 11 )2、-(SO2)R 11 or -N(R 11 )2, wherein the “C3-C8 cycloalkyl”, “C3-C8 cycloalkylC1-C8 alkyl”, “aryl”, “heterocyclyl”, “arylC1-C8 alkyl” or “heterocyclylC1-C8 alkyl” is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C8 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R2 is hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, Wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally selected from halogen, cyano, nitro, C3-C8 cycloalkyl, tri-C1-C8 alkylsilyl, cycloalkenyl, heterocyclyl, aryl, wherein the “C3-C8 cycloalkyl”, “C3-C8 cycloalkenyl”, “heterocyclyl” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C8 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; X 11 Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl or arylC1-C8 alkyl, wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 or -N(R 11 )2, wherein the “C3-C8 cycloalkyl”, “C3-C8 cycloalkylC1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenylC1-C8 alkyl”, “heterocyclyl”, “heterocyclylC1-C8 alkyl”, “aryl” or “arylC1-C8 alkyl” is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-substituted C1-C8 alkyl, halo-substituted C2-C8 alkenyl, halo-substituted C2-C8 alkynyl, halo-substituted C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C8 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; X 13 、X 14 Each independently represents hydrogen, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxyC1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, aryl, arylC1-C8 alkyl, heterocyclyl or heterocyclylC1-C8 alkyl, or the group CX 13 X 14 Together they form a 5- to 8-membered carbon ring or a heterocyclic ring containing oxygen, sulfur or nitrogen, or the group NX 13 X 14 Formed together Wherein, the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 or -N(R 11 )2, wherein the “C3-C8 cycloalkyl”, “C3-C8 cycloalkylC1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenylC1-C8 alkyl”, “aryl”, “arylC1-C8 alkyl”, “heterocyclyl” or “heterocyclylC1-C8 alkyl” is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenatedC1-C8 alkyl, halogenatedC2-C8 alkenyl, halogenatedC2-C8 alkynyl, halogenatedC3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C8 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-, the "5- to 8-membered carbon ring or heterocycle containing oxygen, sulfur or nitrogen" is unsubstituted or substituted with at least one group selected from C1-C8 alkyl, C1-C8 alkoxycarbonyl or benzyl, or forms a condensed ring structure with an aryl or heterocyclic group; is unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl; R 11 Each independently represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.

3. The isoxazoline-substituted benzamide compound, its stereoisomers and agriculturally or veterinarily acceptable salts according to claim 1, characterized in that: Z is hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio or C1-C6 alkylsulfonyl; R1 is hydrogen, halogen, hydroxy, cyano, amino, nitro, formyl, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy C1-C6 alkyl, halo C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl, aryl, heterocyclyl, aryl C1-C6 alkyl or heterocyclyl C1-C6 alkyl, wherein, The "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(CO)N(R 11 )2、-(SO2)R 11 or -N(R 11 )2, wherein the "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C6 alkyl", "aryl", "heterocyclyl", "arylC1-C6 alkyl" or "heterocyclylC1-C6 alkyl" is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C6 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl, Wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally selected from halogen, cyano, nitro, C3-C6 cycloalkyl, tri-C1-C6 alkylsilyl, cycloalkenyl, heterocyclyl, aryl, wherein the “C3-C6 cycloalkyl”, “C3-C6 cycloalkenyl”, “heterocyclyl” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C6 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; X 11 Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl or arylC1-C6 alkyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 or -N(R 11 )2, wherein the “C3-C6 cycloalkyl”, “C3-C6 cycloalkylC1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenylC1-C6 alkyl”, “heterocyclyl”, “heterocyclylC1-C6 alkyl”, “aryl” or “arylC1-C6 alkyl” is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-substituted C1-C6 alkyl, halo-substituted C2-C6 alkenyl, halo-substituted C2-C6 alkynyl, halo-substituted C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C6 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; X 13 、X 14 Each independently represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, aryl, arylC1-C6 alkyl, heterocyclyl or heterocyclylC1-C6 alkyl, or the group CX 13 X 14 Together they form a 5- to 8-membered carbon ring or a heterocyclic ring containing oxygen, sulfur or nitrogen, or the group NX 13 X 14 Formed together Wherein, the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally substituted by halogen, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 or -N(R 11 )2, wherein the “C3-C6 cycloalkyl”, “C3-C6 cycloalkylC1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenylC1-C6 alkyl”, “aryl”, “arylC1-C6 alkyl”, “heterocyclyl” or “heterocyclylC1-C6 alkyl” is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-substituted C1-C6 alkyl, halo-substituted C2-C6 alkenyl, halo-substituted C2-C6 alkynyl, halo-substituted C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR 11 、-SR 11 、-(CO)OR 11 、-(SO2)R 11 、-N(R 11 )2 or -O-(C1-C6 alkylene)-(CO)OR 11 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-, the "5- to 8-membered carbon ring or heterocycle containing oxygen, sulfur or nitrogen" is unsubstituted or substituted with at least one group selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl or benzyl, or forms a condensed ring structure with an aryl or heterocyclic group; is unsubstituted or substituted by at least one group selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl; R 11 Each independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy; Preferably, the compound is selected from any one of Table 1, Table A, and Table B.

4. An isoxazoline-substituted benzamide compound having a chiral center as shown in Formula I', its stereoisomers and agriculturally or veterinarily acceptable salts: in, The substituents Q, X, Y, Z, M, R1, and R2 are defined as shown in any one of claims 1 to 3, and R1 is not hydrogen; the carbon atom at position 2 is a chiral center, and based on the content of stereoisomers having R and S configurations at this position, it has a stereochemical purity of 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), further preferably 90-100% (R), and even more preferably 95-100% (R).

5. An isoxazoline-substituted benzamide compound having a chiral center as shown in Formula I", its stereoisomers and agriculturally or veterinarily acceptable salts: in, The substituents Q, X, Y, Z, M, R1, and R2 are as defined in any one of claims 1 to 3, and R1 is not hydrogen; Based on the content of stereoisomers having R and S configurations at position 5, it has a stereochemical purity of 60-100% (S), preferably 70-100% (S), more preferably 80-100% (S), further preferably 90-100% (S), and even more preferably 95-100% (S); The carbon atom at position 2 is a chiral center. Based on the content of stereoisomers with R and S configurations at this position, it has a stereochemical purity of 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), further preferably 90-100% (R), and even more preferably 95-100% (R).

6. A method for preparing the isoxazoline-substituted benzamide compound, its stereoisomers and agriculturally or veterinarily acceptable salts according to any one of claims 1 to 5, comprising the following steps: The compound represented by general formula II is reacted with the compound represented by general formula III or a salt thereof (such as hydrochloride) in the presence of a condensing agent to obtain a compound represented by general formula I. The chemical reaction equation is as follows: Wherein, P represents OH or halogen, preferably Cl; the substituents Q, X, Y, Z, M, R1 and R2 are defined as shown in any one of claims 1 to 5; Preferably, the condensing agent is PyBOP, HATU, HOBt-EDCI, CDI, DCC or DBU; more preferably, the reaction is carried out in the presence of a base and a solvent; further preferably, the solvent is selected from at least one of dichloromethane, dichloroethane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, toluene, and xylene; and the base is selected from at least one of triethylamine, trimethylamine, DIPEA and NMM.

7. An insecticidal composition, characterized in that The invention comprises a biologically effective amount of at least one of the isoxazoline-substituted benzamide compound according to any one of claims 1 to 5, its stereoisomers and agriculturally or veterinarily acceptable salts; preferably, further comprising a formulation adjuvant.

8. A method for controlling pests, characterized in that: The method comprises contacting the pest or its environment with a biologically effective amount of the isoxazoline-substituted benzamide compound according to any one of claims 1 to 5, its stereoisomers and agriculturally or veterinarily acceptable salts, or the composition according to claim 7.

9. Use of the isoxazoline-substituted benzamide compound according to any one of claims 1 to 5, its stereoisomers and agriculturally or veterinarily acceptable salts, or the composition according to claim 7 in controlling pests.

10. An intermediate, as shown in formula II of claim 6.

Images