Isoxazoline compound and preparation method therefor, herbicidal composition, and use

Abstract

NOT VISIBLE DUE TO STATUS OF PATENT

Description

Isoxazoline compound, preparation method thereof, herbicide composition and application thereof Technical Field

[0001] The present invention belongs to the technical field of pesticides, and in particular relates to an isoxazoline compound, a preparation method thereof, a herbicidal composition and applications thereof. Background Art

[0002] Weed control is a crucial step in achieving efficient agriculture. Despite the diverse range of herbicides on the market, the herbicidal performance and crop selectivity of these known compounds are far from satisfactory. Furthermore, the ever-expanding market, the emergence of weed resistance, the longevity and affordability of these drugs, and the growing concern for the environment necessitate continuous research and development of new, highly effective, safe, and economical herbicides with diverse modes of action. Summary of the Invention

[0003] The present invention provides an isoxazoline compound, a preparation method thereof, a herbicidal composition and application thereof. The compound has excellent herbicidal activity and crop safety.

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

[0005] An isoxazoline compound or a salt thereof as shown in formula I:

[0006] Wherein, X is an aryl group or a heterocyclic group;

[0007] Y is halogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR, -SR, -alkylene-OR, -alkylene-O(CO)R, -alkylene-SR, -(CO)OR, or -(CO)R;

[0008] Z is hydrogen, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, haloalkyl, haloalkenyl, haloalkynyl, cyanoalkyl, -OR, -SR, -N(R)2, -alkylene-OR, -alkylene-SR, -alkylene-N(R)2, -(CO)OR, -alkylene-(CO)OR, -alkylene-(CO)N(R)2, -(CO)N(R)2, aryl, heterocyclyl, arylalkyl, or heterocyclylalkyl;

[0009] R1 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, -alkylene-OR, -alkylene-SR, -alkylene-(SO)R, -alkylene-(SO)2R, -alkylene-(CO)OR, -alkylene-(CO)N(R)2, -alkylene-(CO)NR(OR), -alkylene-ON═C(R)2, -alkylene-(CO)ON═C(R)2, aryl, heterocyclyl, or alkyl, alkenyl, or alkynyl substituted with at least one group selected from halogen, cycloalkyl, cycloalkenyl, heterocyclyl, or aryl;

[0010] R2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, heterocyclyl, arylalkyl, heterocyclylalkyl, -alkylene-OR, -alkylene-SR, cyanoalkyl, -(CO)OR, -SO2R, or -SO2N(R)2;

[0011] Or R1 and R2 together form -(CH2) which is unsubstituted or substituted by at least one group selected from alkyl, halogen or oxo. n -;

[0012] n is 3, 4, or 5;

[0013] R3 is O, NH or N-alkyl;

[0014] Q1 and Q2 are independently O or S;

[0015] The aforementioned cycloalkyl, cycloalkenyl, aryl or heterocyclic group is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR, -SR, -alkylene-OR, -alkylene-SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, -S02R, -OS02R, -N(R)2 or -NR(OR);

[0016] R each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl substituted by at least one group selected from halogen, hydroxy, alkoxy, cyano, trialkylsilyl, phenyl or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, heterocyclic radical, or phenyl or heterocyclic radical substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, haloalkoxy, phenyl or halophenyl; or N(R)2 together form

[0017] In a specific embodiment, Y is halogen, cyano, 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, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, -OR, -SR, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-O(CO)R, -(C1-C8 alkylene)-SR, -(CO)OR, or -(CO)R;

[0018] Z is hydrogen, halogen, 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, halo-substituted C1-C8 alkyl, halo-substituted C2-C8 alkenyl, halo-substituted C2-C8 alkynyl, cyano-C1-C8 alkyl, -OR, -SR, -N(R)2, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, -(C1-C8 alkylene)-N(R)2, -(CO)OR, -(C1-C8 alkylene)-(CO)OR, -(C1-C8 alkylene)-(CO)N(R)2, -(CO)N(R)2, aryl, heterocyclyl, arylC1-C8 alkyl or heterocyclylC1-C8 alkyl;

[0019] R1 is hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, -(C1-C8 alkylene)-(SO)R, -(C1-C8 alkylene)-(SO)2R, -(C1-C8 alkylene)-(CO)OR, -(C1-C8 alkylene)-(CO) N(R)2, -(C1-C8 alkylene)-(CO)NR(OR), -(C1-C8 alkylene)-ON=C(R)2, -(C1-C8 alkylene)-(CO)ON=C(R)2, aryl, heterocyclyl, or C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted by at least one group selected from halogen, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl or aryl;

[0020] R2 is 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, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, aryl, heterocyclyl, arylC1-C8 alkyl, heterocyclylC1-C8 alkyl, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, cyanoC1-C8 alkyl, -(CO)OR, -SO2R or -SO2N(R)2;

[0021] Or R1 and R2 together form -(CH2)n which is unsubstituted or substituted by at least one group selected from C1-C8 alkyl, halogen or oxo;

[0022] n is 3, 4, or 5;

[0023] R3 is O, NH or N-(C1-C8 alkyl);

[0024] The aforementioned C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl or heterocyclic group is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, -OR, -SR, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, -S02R, -OS02R, -N(R)2 or -NR(OR);

[0025] R independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted by at least one group selected from halogen, hydroxy, C1-C8 alkoxy, cyano, tri-C1-C8 alkylsilyl, phenyl or C1-C8 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 Cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl, heterocyclyl, or phenyl or heterocyclyl 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, halogenated C1-C8 alkoxy, phenyl or halogenated phenyl; or N(R)2 together form

[0026] In another specific embodiment, Y is halogen, cyano, 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, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, -OR, -SR, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-O(CO)R, -(C1-C6 alkylene)-SR, -(CO)OR, or -(CO)R;

[0027] Z is hydrogen, halogen, 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, halo-substituted C1-C6 alkyl, halo-substituted C2-C6 alkenyl, halo-substituted C2-C6 alkynyl, cyano-C1-C6 alkyl, -OR, -SR, -N(R)2, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-SR, -(C1-C6 alkylene)-N(R)2, -(CO)OR, -(C1-C6 alkylene)-(CO)OR, -(C1-C6 alkylene)-(CO)N(R)2, -(CO)N(R)2, aryl, heterocyclyl, arylC1-C6 alkyl or heterocyclylC1-C6 alkyl;

[0028] R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-SR, -(C1-C6 alkylene)-(SO)R, -(C1-C6 alkylene)-(SO)2R, -(C1-C6 alkylene)-(CO)OR, -(C1-C6 alkylene)-(CO) N(R)2, -(C1-C6 alkylene)-(CO)NR(OR), -(C1-C6 alkylene)-ON=C(R)2, -(C1-C6 alkylene)-(CO)ON=C(R)2, aryl, heterocyclyl, or C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl substituted by at least one group selected from halogen, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl or aryl;

[0029] R2 is 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, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, aryl, heterocyclyl, arylC1-C6 alkyl, heterocyclylC1-C6 alkyl, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-SR, cyanoC1-C6 alkyl, -(CO)OR, -SO2R or -SO2N(R)2;

[0030] Or R1 and R2 together form -(CH2)n which is unsubstituted or substituted by at least one group selected from C1-C6 alkyl, halogen or oxo;

[0031] n is 3, 4, or 5;

[0032] R3 is O, NH or N-(C1-C6 alkyl);

[0033] The aforementioned C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl or heterocyclic group is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, -OR, -SR, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, -S02R, -OS02R, -N(R)2 or -NR(OR);

[0034] R independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl substituted by at least one group selected from halogen, hydroxy, C1-C6 alkoxy, cyano, tri-C1-C6 alkylsilyl, phenyl or C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 Cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl, heterocyclic group, or phenyl or heterocyclic group 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, halo-C1-C6 alkoxy, phenyl or halophenyl; or N(R)2 together form

[0035] In another embodiment, R3 is NH; Q1 and Q2 are each independently O.

[0036] In another embodiment, R1 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, haloalkyl, haloalkenyl, haloalkynyl, -alkylene-(CO)OR, -alkylene-(CO)N(R)2, -alkylene-ON=C(R)2, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl.

[0037] In another specific embodiment, R1 is 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, halo-substituted C1-C8 alkyl, halo-substituted C2-C8 alkenyl, halo-substituted C2-C8 alkynyl, -(C1-C8 alkylene)-(CO)OR, -(C1-C8 alkylene)-(CO)N(R)2, -(C1-C8 alkylene)-ON=C(R)2, aryl, heterocyclyl, arylC1-C8 alkyl or heterocyclylC1-C8 alkyl.

[0038] In another specific embodiment, R1 is 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, halo-substituted C1-C6 alkyl, halo-substituted C2-C6 alkenyl, halo-substituted C2-C6 alkynyl, -(C1-C6 alkylene)-(CO)OR, -(C1-C6 alkylene)-(CO)N(R)2, -(C1-C6 alkylene)-ON=C(R)2, aryl, heterocyclyl, arylC1-C6 alkyl or heterocyclylC1-C6 alkyl.

[0039] In the definitions 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 terms, represent the following substituents: Alkyl groups having more than two carbon atoms may be straight-chain or branched. For example, in the compound term "-alkylene-OR," alkylene may be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. Alkyl groups include, 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; and C6 alkyl-hexyl, such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, vinyl, allyl, 1-methylprop-2-ene-1-yl, 2-methylprop-2-ene-1-yl, but-2-ene-1-yl, but-3-ene-1-yl, 1-methylbut-3-ene-1-yl and 1-methylbut-2-ene-1-yl. Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds can be at any position of each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system with, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl with, for example, three to six carbocyclic ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein double bonds can be at any position. Halogen is fluorine, chlorine, bromine or iodine.

[0040] 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

[0041] 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.

[0042] 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.

[0043] The present invention provides an isoxazoline compound having a chiral center or a salt thereof as shown in Formula I':

[0044] wherein the carbon atom (C*) at position 2 and / or 5 is a chiral center, the substituents R1, R2, R3, Q1, Q2, X, Y and Z are as defined above, and Z is not hydrogen;

[0045] Based on the content of stereoisomers having R and S configurations at position 2, 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); or 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);

[0046] and / or based on the carbon atom at position 5 being a chiral center, based on the content of stereoisomers having R and S configurations at this position, 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); or 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).

[0047] Here, "stereochemical purity" refers to the percentage of the amount of the stereoisomer to the total amount of stereoisomers having a chiral center.

[0048] In the present invention, the stereochemical configuration at the position marked * in Formula I is determined according to the Cahn-Ingold-Prelog system as predominantly (R) or (S), however, the subject matter of the present invention also relates to all stereoisomers at other positions encompassed by Formula I, and mixtures thereof. Such compounds of Formula I may contain, for example, one or more additional asymmetric carbon atoms or other double bonds not specifically described in 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 position marked * is in the R- or S-configuration, or in mixtures in which compounds or compounds of the same chemical structure have the R- or S-configuration at the position marked *, or are present in a proportion in which the compound having the R- or S-configuration is predominant (at least 60% R- or S-configuration), 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 positions marked with * are met, possible stereoisomers defined by specific spatial forms, such as enantiomers, diastereomers, Z- and E-isomers, are included in 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.

[0049] If various functional groups are present, the present invention also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0050] 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.

[0051] The preparation method of the isoxazoline compound comprises the following steps:

[0052] (1) The compound represented by the general formula II is reacted with the compound represented by the general formula III or a salt thereof (such as hydrochloride) to obtain the compound represented by the general formula I. The reaction equation is as follows:

[0053] Or (2) reacting the compound represented by the general formula IV with the compound represented by the general formula V or a salt thereof (such as hydrochloride) to obtain the compound represented by the general formula I, wherein the reaction equation is as follows:

[0054] Or (3) reacting the compound represented by the general formula VI with the compound represented by the general formula VII to obtain the compound represented by the general formula I, wherein the reaction equation is as follows:

[0055] wherein M and M1 independently represent OH or halogen, Hal represents halogen, and the substituents R1, R2, R3, Q1, Q2, X, Y and Z are as defined above.

[0056] In one embodiment, the reactions (1) and (2) are respectively carried out in the presence of a solvent; in another embodiment, a base and / or a condensing agent is added during the reaction.

[0057] In another specific embodiment, the base is selected from at least one of an inorganic base (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KHCO3, KF, CsF, KI, NaI, K3PO4, K2HPO4, NaOH, KOH, NaH, KH, etc.) or an organic base (such as DMAP, pyrazole, triethylamine, DIEA / DIPEA, potassium trimethylsilanolate, AcOK, AcONa, MeONa, EtONa, t-BuONa, etc.).

[0058] In another embodiment, the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU or HATU.

[0059] In another embodiment, the solvent is selected from at least one of DMF, DMA, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran or ethyl acetate.

[0060] In one embodiment, the reaction (3) is carried out in the presence of a base and a solvent.

[0061] In another specific embodiment, the base is selected from at least one of an inorganic base (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KHCO3, KF, CsF, KI, NaI, K3PO4, K2HPO4, NaOH, KOH, NaH, KH, etc.) or an organic base (such as DMAP, pyrazole, triethylamine, DIEA / DIPEA, potassium trimethylsilanolate, AcOK, AcONa, MeONa, EtONa, t-BuONa, etc.).

[0062] In another embodiment, the solvent is selected from at least one of methanol, ethanol, isopropanol, DMF, DMA, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran or ethyl acetate.

[0063] In another embodiment, when M 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:

[0064] The compound represented by general formula IV is prepared by reacting the compound represented by general formula V with the compound represented by general formula VI. The reaction chemical equation is as follows:

[0065] Wherein, W represents a C1-C6 alkyl group or a phenyl group.

[0066] In addition, the compounds of the present invention can be prepared by referring to the methods shown in CN201280017007.3 and the like.

[0067] An intermediate, such as described in Formula II, Formula III, Formula V or Formula VI.

[0068] A herbicide composition comprises a herbicidally effective amount of at least one of the isoxazoline compounds; preferably, further comprises a formulation adjuvant; more preferably, further comprises other active ingredients.

[0069] A method for controlling weeds comprises applying a herbicidally effective amount of at least one of the isoxazoline compounds or the herbicide composition on plants or weedy areas.

[0070] The use of at least one of the isoxazoline compounds or the herbicide composition in controlling weeds, preferably, the isoxazoline compound is used to control weeds in useful crops, wherein the useful crops are transgenic crops or crops treated with genome editing technology.

[0071] The compounds of formula I of the present invention have outstanding herbicidal activity against many economically important monocotyledonous and dicotyledonous harmful plants. The active substances of the present invention are also effective against perennial weeds that grow from rhizomes, rootstocks, or other perennial organs and are difficult to control. In this regard, it is generally unimportant whether the substance is used before sowing, before germination, or after germination. Representative examples of monocotyledonous and dicotyledonous weed groups that can be controlled by the compounds of the present invention are mentioned in particular, without being limited to specific species. Examples of weed species on which the active substances are effective include monocotyledonous plants: annual Avena, Secale, Grass, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria, and Cyperus, and perennial Agropyron, Cyperus, Imperata, and Sorghum, as well as perennial Cyperus.

[0072] Regarding dicotyledonous weed species, its activity extends to species such as annual Galium, Viola, Veronica, Sesame, Chickweed, Amaranthus, Sinapsis, Ipomoea, Glechoma, Matricaria, and Abutilon, as well as perennial weeds such as Convolvulus, Thistle, Rumex, and Artemisia. The active ingredients of the present invention effectively control harmful plants such as Echinochloa, Sagittaria, Alisma, Eriocheir, Saccharum, and Cyperus under unspecified conditions during rice sowing. If applied to the soil surface before germination, the weed seedlings can be completely prevented from emerging, or growth can be halted as soon as the cotyledons emerge, ultimately resulting in complete death after three to four weeks. The compounds of the present invention are particularly active against Apia, Sesame, Polygonum convolvulus, Chickweed, Ivy-leaved Veronica, Veronica arabicum, Pansy, Amaranthus, Galium, and Kochia.

[0073] While the compounds of the present invention exhibit excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they cause no damage, or only minimal damage, to economically important crop plants such as wheat, barley, rye, rice, corn, sugar beets, cotton, and soybeans. They are particularly compatible with cereal crops such as wheat, barley, and corn, particularly wheat. Therefore, the compounds of the present invention are well suited for selectively controlling undesirable plants in agricultural or ornamental crops.

[0074] Due to their herbicidal properties, these active substances can be used to control harmful plants in known or upcoming genetically engineered plant cultivation. Transgenic plants often possess superior properties, such as resistance to specific pesticides, especially herbicides, or resistance to plant diseases or their causative microorganisms, such as specific insects or fungal, bacterial, or viral microorganisms. Other specific properties are related to the product's characteristics, such as quantity, quality, storage stability, composition, and specific ingredients. Thus, transgenic plant products are known to be obtained with increased starch content, improved starch quality, or a different fatty acid composition.

[0075] The compounds of formula I according to the present invention or their salts are preferably used in the cultivation of economically important genetically modified crops and ornamental plants, for example cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn, or in the cultivation of sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetable plants. The compounds of formula I are preferably used in the cultivation of useful plants with herbicides which are resistant or have been rendered resistant to the toxic effects of the herbicides by genetic engineering.

[0076] Conventional methods for breeding plants with improved traits compared to known plants include, for example, conventional mating methods and mutant breeding. In other words, new plants with improved traits can be obtained by means of genetic engineering methods (see, for example, EP-0221044A, EP-0131624A). For example, several methods have been described:

[0077] - genetic engineering of crop plants to improve starch synthesis in plants (e.g. WO 92 / 11376, WO 92 / 14827, WO 91 / 19806);

[0078] - transgenic crop plants resistant to specific herbicides, such as glufosinate herbicides (e.g. EP-0242236 A, EP-0242246 A) or glyphosate herbicides (WO 92 / 00377), or sulfonylurea herbicides (EP-0257993 A, US Pat. No. 5,013,659 A);

[0079] - genetically modified crop plants, such as cotton, that produce Bacillus thuringiensis toxins (Bt toxins) that protect against attack by certain pests (EP-0142924 A, EP-0193259 A);

[0080] - Transgenic crop plants with improved fatty acid composition (WO 91 / 13972).

[0081] Numerous molecular biotechniques are known for producing transgenic plants with improved traits (see, for example, Sambrook et al., 1989, Molecular Amplification, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York; or Winnacker, "Gene und Klone," VCH Weinheim, 2nd ed., 1996, or Christou, "Trends in Plant Science," 1 (1996), 423-431). To carry out genetic engineering operations, nucleic acid molecules can be introduced into plasmids, and mutations or sequence changes can be generated by recombination of DNA sequences. Using the standard methods described above, for example, substrates can be exchanged, partial sequences can be removed, or natural or synthetic sequences can be added. To connect DNA fragments to one another, it is possible to attach binding partners or linkers to the fragments.

[0082] Plant cells in which the activity of a gene product is reduced can be prepared, for example, by expressing at least one appropriate antisense RNA, sense RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the gene product.

[0083] For this purpose, it is possible to use a DNA molecule that comprises the entire coding sequence of the gene product, including any flanking sequences that may be present, and to use a DNA molecule that comprises only a portion of the coding sequence, which portion must be long enough to achieve an antisense effect in the cell. Sequences that are highly homologous to the coding sequence of the gene product, but not identical thereto, can also be used.

[0084] When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired plant cell compartment. However, in order to localize in a specific compartment, it is possible, for example, to link the coding region to the DNA sequence to ensure localization at a specific position. These sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992) 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 65 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

[0085] Transgenic plant cells can be incorporated into whole plants using known techniques. Transgenic plants can be of any desired plant variety, i.e., monocotyledons and dicotyledons. In this way, it is possible to obtain transgenic plants with improved traits by overexpressing, inhibiting or suppressing homologous (=natural) genes or gene sequences, or by expressing heterologous (=foreign) genes or gene sequences.

[0086] When the active substances of the present invention are used on genetically modified crops, in addition to the harmful plant growth inhibitory effects observed on other crops, they often exhibit specific effects on the corresponding genetically modified crops, such as improved or expanded weed control, improved application rates, preferably a good combination of the resistance of the genetically modified crop and the performance of the herbicide, and effects on the growth and yield of the genetically modified crop plants. Therefore, the present invention also provides the use of the compounds as herbicides for controlling harmful plants in genetically modified crop plants.

[0087] Furthermore, the compounds of the present invention can significantly regulate the growth of crop plants. By modulating plant metabolism, these compounds can be used to control plant composition and promote harvest, for example by causing plant desiccation and dwarfing. Furthermore, they are suitable for regulating and inhibiting undesirable plant growth without disrupting crop growth. Inhibiting plant growth plays a very important role in many monocotyledonous and dicotyledonous crops because it can reduce or completely prevent lodging.

[0088] The compound of the present invention can be applied using general formulations, and wettable powders, emulsion concentrates, sprayable solutions, powders or granules can be used. Thus, the present invention also provides herbicidal compositions comprising compounds of formula I. According to common biological and / or chemical physical parameters, compounds of formula I can be formulated in a variety of ways. Suitable formulation selection examples are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsion concentrates (EC), emulsions such as oil-in-water dispersions and water-in-oil dispersions (EW), sprayable solutions, suspension concentrates (SC), dispersible oil suspensions (OD), suspensions with oil or water as diluents, solutions of miscible oils, powders (DP), capsule suspensions (CS), seeded compositions, granules for broadcasting and soil application, spray granules, coated granules and absorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV (ultra-low volume) formulations, microcapsules and wax products. These individual formulation types are known and are described, for example, in Winnacker-Küchler, "Chemische Techonologie" [Chemical Technology], Vol. 7, C. Hauser Verlag Munich, 4th edition 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973; K. Martens, "Spray Drying" Handbook, 3rd edition 1979, G. Goodwin Ltd. London.

[0089] Necessary formulation auxiliaries, such as inert substances, surfactants, solvents and other additives are likewise known and described in, for example, Watkins, "Handbook of Powder Diluents, Pesticides and Carriers," 2nd ed., Darland, Caldwell, NJ; Hvophen, "Introduction to Clay Colloid Chemistry," 2nd ed., J. Wiley and Sons, NY; C. Marsden, "Solvent Guide," 2nd ed., Interscience, NY 1963; McCutcheon, "Detergents and Emulsifiers Annual," MC Publishing Company, Ridgewood, NJ; Sisley and Wood, "Encyclopedia of Surfactants," Chemical Publishing Company, NY 1964; of" "[Ethylene oxide adduct surfactants], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Küchler "Chemische Technologie" [Chemical Technology], Vol. 7, C. Hauser Verlag Munich, 4th edition 1986.

[0090] Wettable powders are homogeneously dispersible in water and contain, in addition to the active substance, a diluent or inert substance, ionic and nonionic surfactants (wetting agents, dispersants), for example, polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkylsulfonates, alkylphenylsulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthomethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. To prepare wettable powders, the herbicide active substance is finely ground, for example using conventional apparatus such as hammer mills, fan mills or jet mills, and the adjuvants are mixed in simultaneously or sequentially.

[0091] The concentrated emulsion is prepared by dissolving the active substance in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene or a mixture of relatively high-boiling aromatic compounds or hydrocarbons or solvents, and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.

[0092] Powders are obtained by grinding the active substance with finely divided solid materials, such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspensions in water or oil can be prepared, for example, by wet grinding using a commercially available bead mill, with or without the addition of a surfactant of the type described above for the other formulations.

[0093] Emulsions such as oil-in-water emulsions (EW) can be prepared using aqueous organic solvents using stirrers, colloid mills and / or static mixers and, if desired, adding surfactants of another formulation type as described above.

[0094] Granules can be prepared by spraying the active substance onto an adsorbent and granulating with an inert material, or by concentrating the active substance onto the surface of a carrier such as sand or kaolinite and granulating the inert material with a binder such as polyvinyl alcohol, sodium polyacrylate, or mineral oil. Suitable active substances can be granulated using methods for preparing fertilizer granules and, if desired, mixed with fertilizers. Aqueous suspension granules can be prepared using conventional methods, such as spray drying, fluidized bed granulation, disc granulation, mixing using a high-speed mixer, and extrusion in the absence of solid inert materials.

[0095] For the preparation of granules using a mill, fluidized bed, extruder, and spraying, see, for example, the following processes: "Spray Drying Handbook," 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, "Agglomeration," Chemistry and Engineering, 1967, pp. 147ff; "Perry's Chemical Engineer's Handbook," 5th ed., McGraw-Hill, New York, 1973, pp. 8-57. For the formulation of crop protection products, see, for example, G. C. Lingman, "Weed Control as a Science," John Wiley & Sons, New York, 1961, pp. 81-96 and J. D. Frieder, S. A. Evans, "Weed Control Handbook," 5th ed., Blackwell Scientific Research, Oxford, 1968, pp. 101-103.

[0096] Agrochemical formulations typically contain 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the active substance of Formula I. The active substance concentration in wettable powders is, for example, from about 10 to 99% by weight, with the formulation components typically comprising the remainder to 100% by weight. The active substance concentration in emulsifiable concentrates can range from about 1 to 90% by weight, preferably 5 to 80%. Powder formulations contain 1 to 30% by weight of active substance, typically preferably 5 to 20% by weight, while sprayable solutions contain approximately 0.05 to 80% by weight, preferably 2 to 50% by weight. The active substance content in water-suspendable granules depends primarily on whether the active substance is liquid or solid, and on the adjuvants, fillers, etc. used in granulation. The active substance content in water-suspendable granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

[0097] The active substance formulations may additionally include tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and, generally, pH and viscosity regulators which are customary in each case.

[0098] Based on these formulations, it is also possible to mix with other pesticide active substances such as insecticides, acaricides, herbicides and fungicides, as well as with safeners, fertilizers and / or plant growth regulators, either as premixes or as canned mixes.

[0099] In mixed formulations or tank-mixed formulations, suitable active substances that can be mixed with the active substance of the present invention are, for example, known substances described in "World New Pesticide Variety Technology Encyclopedia", China Agricultural Science and Technology Press, September 2010, and the literature cited therein. For example, the following herbicide active substances can be mixed with the mixture of formula I (Note: the name of the compound is either the common name according to the International Organization for Standardization (ISO) or the chemical name, with a code number when appropriate): acetochlor, butachlor, alachlor, isopropyl metolachlor, isopropyl metolachlor, S-isopropyl metolachlor, pretilachlor, acetochlor, acetochlor, naphthiachlor, R-(l-)naphthiachlor, propanil, mefenacet, bisbencarb, fluazifop, flufenacet, cyfluthrin, flumethalin, bromomethalin, dimethathiachlor, high-efficiency dimethathiachlor, ethoxymethalin, flufenacet, methoxymethalin, metazachlor, isopropyltrimonium chloride, high-efficiency cyfluthrin, Dipropylene glycol, pethoxachlor, butyrac, cyproconazole, flumethalin, heptamiprole, isobutachlor, propargyl chloramine, terbutachlor, dimethylaminopropylamine, dimethoate, chlorfenapyr, trimethylcyclohexane, chlorfenapyr, propyracyl chloramine, valeryl chloramine, carbamyl, new Yanling, tricyclic chlorfenapyr, butenesulfonamide, butenesulfonamide, mesotrione, benzylchlor, quinone, benzfluorosulfonamide, naphthamide, acetoacetamide, naphthamide, thiazolin, cypermethrin, benzylchlor, benzylchlor, cypermethrin, benzylchlor, cypermethrin, atrazine, simazine, promethazine, cyanamide, simethazine, ametryn, propazine, isopropylamine, fluroxypyr, terbutylamine, terbutylazine, triazine fluazifone, cyprodinil, gampopazine, thiophanate , Promethazine, Simatolin, Azide, Dichlorvos, Isopropylamine, Cyprodinil, Metazine, Another Butylazine, Second Butylazine, Terbutalone, Methoxypropylamine, Cyanamide, Cyanocyanine, Kolazone, Atrazine, Metazine, Glycyrrhizin, Cyanuric acid, Indaziflam, Chlorsulfuron, Metsulfuron-methyl, Bensulfuron-methyl, Chlorimuron-methyl, Bensulfuron-methyl, Thisulfuron-methyl, Pyrazosulfuron-methyl, Metsulfuron-methyl, Iodosulfuron-methyl sodium salt, Formamidosulfuron-methyl, Ethylsulfuron-methyl, Bensulfuron-methyl, Metsulfuron-methyl, Nicosulfuron, Ethamidosulfuron-methyl, Acesulfuron-methyl, Ethoxysulfuron-methyl, Cyprodinil, Sulfonsulfuron-methyl, Tetrazosulfuron, Fentazuron-methyl, Monosulfuron-methyl, Monosulfuron, Fluazuron-methyl, Flupyrazosulfuron-methyl, Epoxysulfuron Sulfur-methyl, azole pyrazosulfuron, primisulfuron, propensulfuron-methyl, trifloxysulfuron, sulfosulfuron, trifloxysulfuron, trifloxysulfuron, metsulfuron-methyl sodium, primisulfuron, methylthiosulfuron, pyrimidisulfon-methyl, Propyrisulfuron (propyrisulfuron), pyrazosulfuron-methyl, acifluorfen, fomesafen, lactofen, fluazifop-butyl, oxyfluorfen, oxazolidinone, benfibrate, chlorpyrifos ethyl, methylcarboxylic acid butyl, trifluoroacetic acid butyl, methoxy-nitropropane, trifluosuccinate, fluorinated herbicide ether, flutosulfuron, nitropropane, methylpyralid, dimethoate, flutosulfuron, flutosulfuron ester, Halosafen, chlorotoluron, isoproturon, linuron, diuron,Saproron, Fluorouron, Benthiocarb, Methylbenthiocarb, Benthiocarb, Sulfathiocarb, Isoxuron, Terbuthiuron, Clodinuron, Chlorbromon, Methylthiocarb, Acyril, Methoxythiocarb, Bromothiocarb, Methoxythiocarb, Chlorthiocarb, Monisouron, Cyclothiocarb, Fenuron, Flusulfuron, Cyclothiocarb, Cyclothiocarb, Cyclothiocarb, Cyclothiocarb, Thiofuron, Buthiuron, Cyclothiocarb, Parafluron, Methiathiazolin, Lomthiocarb, Trimethylisourea, Oxazol, Monisouron, Anisuron, Methiuron, Chloreturon, Tetrafluron, Betaine, Betaine-ethyl Ester, Betaine, Sulfathiocarb, Terbuthiuron, Avena Cinnamomum, Anipropyrin, Chlorprophion, Diclofenac, Anipropyrin, Chlorpheniramine, Carboxazo le, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbasulam, Butylcarb, Fenasulam ... 2-Methyl-4-chlorobutyric acid, 2,4,5-T, 2,4,5-T propionic acid, 2,4,5-T butyric acid, 2-Methyl-4-chloroamine salt, Mediben, Cypermethrin, Fenpyraclostrobin ... in, propanol, glyphosate, safflower, glufosinate, methylamine glufosinate, glufosinate sulfide, piperphosphine, bialaphos, disulfide, glufosinate, vine glufosinate, valoron, dimethylamino glufosinate, oxalophos, imazapyr, imazapyr, imazapyr, imazapyr, imazapyr ammonium, imazapyr, imazapyr, cloflupyr, cloflupyr 2-ethylhexyl ester, clopyralid, amiloride, triclopyr, dithiopyr, halofop, triclopyralid, thiopyralid, flupyralid, chlorpyrifos, flupyralid, chlorpyrifos, flupyralid, flupyralid, triclopyralid butoxyethyl ester, Cliodinate, sethoxydim, clethodim, cycloxydim, chlorpyrifos, cyclohexanone, butoxydim, oxaclofop, pyraclofop, Buthidazole, metribuzin,Hexazinone, Metamitron, Ethylmetazolin, Ametridione, Amibuzin, Bromoxynil, Octanoyl Bromoxynil, Octanoyl Ioxyl, Ioxyl, Dichlobenil, Diphenylacetonitrile, Dipyridoxal, Hydroxypyridoxal, Iodobonil, Sulfursulfuron, Difluorosulfuron, Penoxsulam, Sulfursulfuron, Chlorosulfuron, Dichlorosulfuron, Pyroxypyramide, Fluorosulfuron, Bispyribac-butyl, Cyclopyramide, Pyroxypyramide, Pyroxypyramide, Bispyribac-butyl, Cyclopyramide, Pyroxypyramide, Bispyribac-butyl, Mesotrione, Sulcotrione, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, Isoxaflutole, Isoxachlorpyrifos, Fenoxasulfone, M Ethiozolin, isopropylpyraclostrobin, pyrasulfobutyl, pyrazoline, wild yanquat, benzylpyrachlor, pyrazoline, pyrasulfotole, benzylpyrazone, pyroxasulfone, pyrazoline, fluazifop, chlorfenapyr, amine pyraclostrobin, pyrazoline, fluazifop, sulfentrazone, Bencarbazone, bispyribac, fluazifop-butyl, bromocriptine, isothiocyanate, cypermethrin, cypermethrin, terclopyralid, Flupropacil, indolone, flumethoxal, fluazifop-butyl, cypermethrin, phthalein, Flumezin, pentachlorophenol (sodium), dinitrophenol, dinitrophenol, dinitrophenol, dioxin, dioxetone, oxadiazol, oxadiazol, cyclopentane Fluazifop, flumethoxam, fluazifop-butyl, tetrazolam, flupyridazone, herbicide-resistant, bromomyxin, dimethylpyridazone, pyridafol, quinclorac, quinmechlor, bentazon, pyridazone, oxaziclomefop, chlorpyrifos, isopropylpyridazone, cyproconazole, isopropylpyridazone, indole, sodium chlorate , dalapon, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, grass fast, bromophenol oxime, triazole sulfonate, methomyl, furochlor, furochlor, ethyl furochlor, chloranil, chlorthalid, fluchloralidone, barnyard grass, acrolein, benzylpyridinium chloride, benzylpyridinium chloride, avena sativa ester, thiadiazole, cotton amine, hydroxythiocarb, methoxybenzone, benzylpyridinium chloride, chloranil, trichloropropionic acid, Al orac, Diethamquat, Etnipromid, Iprymidam, Ipfencarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapin, Methylsulfuron, Cambendichlor, Cyprodinil, Thiencarbazone, Fenthiocyanate ...D489, LS82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO5 35. DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023. ,

[0100] When used, if necessary, commercially available formulations are diluted in a common manner, for example, in the case of wettable powders, concentrated emulsions, suspensions and granules suspended in water, with water dilution. Powders, granules used for soil application or solutions for broadcasting and spraying generally do not require further dilution with an inert substance before use. The required use amount of the compound of formula I varies with external conditions, such as temperature, humidity, the nature of the herbicide used, etc. It can have a large range of variation, for example between 0.001 and 1.0 kg ai / ha, or more active substance, but preferably between 0.005 and 750 g ai / ha, particularly between 0.005 and 250 g ai / ha. DETAILED DESCRIPTION

[0101] 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.

[0102] 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.

[0103] Table 1 Compound structures and their 1 H NMR

[0104] Tables AF are constructed in the same manner as Table 1 above, except that the compounds of formula I are replaced with compounds of formula I' having a chiral center. In Table A, the entries under the "Serial Number" column heading are sequentially recited as 1(2R)-21(2R), 23(2R)-232(2R), 234(2R)-353(2R), 355(2R)-365(2R), 367(2R)-454(2R), 456(2R)-466(2R), 468(2R)-474(2R), 476(2R)-481(2R), and 483(2R)-486(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. In Table B, the entries under the "Serial Number" column heading are sequentially recited as 1(2S)-21(2S), 23(2S)-232(2S), 234(2S)-353(2S), 355(2S)-365(2S), 367(2S)-454(2S), 456(2S)-466(2S), 468(2S)-474(2S), 476(2S)-481(2S), and 483(2S)-486(2S). For example, 1(2S) corresponds to a compound in which the 2-position of compound 1 in Table 1 has an S configuration. In Table C, the entries under the "Serial Number" column heading are sequentially recited as 1(5S)-486(5S). For example, 1(5S) corresponds to a compound in which the 5-position of compound 1 in Table 1 has an S configuration. In Table D, the entries under the "Number" column heading are sequentially recited as 1(5R)-486(5R). For example, 1(5R) corresponds to compound 1 in Table 1 in which the 5-position is in the R configuration.In Table EH, the entries under the "Serial Number" column heading are 1(2S,5S)-21(2S,5S), 23(2S,5S)-232(2S,5S), 234(2S,5S)-353(2S,5S), 355(2S,5S)-365(2S,5S), 367(2S,5S)-454(2S,5S), 456(2S,5S)-466(2S,5S), 468(2S,5S)-474(2S,5S), 476(2S,5S)-481(2S,5S), 483 (2S,5S)-486(2S,5S), 1(2S,5R)-21(2S,5R), 23(2S,5R)-232(2S,5R), 234(2S,5R)-353(2S,5R), 355(2S,5R)-365(2S,5 R), 367(2S,5R)-454(2S,5R), 456(2S,5R)-466(2S,5R), 468(2S,5R)-474(2S,5R), 476(2S,5R)-481(2S,5R), 483(2S,5R) )-486(2S,5R), 1(2R,5S)-21(2R,5S), 23(2R,5S)-232(2R,5S), 234(2R,5S)-353(2R,5S), 355(2R,5S)-365(2R,5S), 367 (2R,5S)-454(2R,5S), 456(2R,5S)-466(2R,5S), 468(2R,5S)-474(2R,5S), 476(2R,5S)-481(2R,5S), 483(2R,5S)-486( 2R,5S), 1(2R,5R)-21(2R,5R), 23(2R,5R)-232(2R,5R), 234(2R,5R)-353(2R,5R), 355(2R,5R)-365(2R,5R), 367(2R,5R) )-454(2R,5R), 456(2R,5R)-466(2R,5R), 468(2R,5R)-474(2R,5R), 476(2R,5R)-481(2R,5R), 483(2R,5R)-486(2R,5R). For example, 1(2S,5S) corresponds to a compound in which both positions 2 and 5 of compound 1 in Table 1 are in S configuration, and 1(2R,5S) corresponds to a compound in which position 2 of compound 1 in Table 1 is in R configuration and position 5 is in S configuration.

[0105] 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.

[0106] 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 in the table below are either commercially available or can be readily prepared by one of ordinary skill in the art.

[0107] Examples of representative compounds are shown below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0108] 1. Synthesis of compound 19(2S)

[0109] (1) 19-1 (0.2 g, 1.0 eq) was dissolved in dichloromethane in a round-bottom flask, and 19-2 (0.26 g, 1.0 eq) was added. EDCI (0.75 g, 2.0 eq) and DMAP (0.11 g, 0.5 eq) were added in sequence. The mixture was reacted at room temperature overnight, extracted with dichloromethane, and the organic phase was dried over anhydrous sodium sulfate. The crude product 19-3 (0.3 g, yield 71%) was obtained after spin drying.

[0110] (2) 19-3 (0.3 g, 1.0 eq) was dissolved in isopropanol in a round-bottom flask, and 19-4 (0.26 g, 1.0 eq) and NaHCO3 (0.58 g, 5.0 eq) were added sequentially. The temperature was raised to 50°C and the reaction was allowed to proceed for two hours. After the reaction, the isopropanol was dried by spin-drying, the mixture was extracted with ethyl acetate, and the organic phase was dried over anhydrous sodium sulfate and purified by column chromatography. 19(2S) was obtained as a white oil by spin-drying (0.33 g, purity 94%, yield 64%).

[0111] 2. Synthesis of compound 21 (2S, 5S)

[0112] (1) In a 50 ml round-bottom flask, 400 mg of compound 21-1 was dissolved in 10 ml of dichloromethane. Triethylamine (3 eq), HOBT (1.2 eq), EDCI (1.2 eq), and 21-2 (1.1 eq) were added in sequence. The mixture was reacted at room temperature overnight. After completion of the reaction, 480 mg of compound 21-3 was obtained by column purification (yield 90%).

[0113] (2) 480 mg of 21-3 was dissolved in 10 ml of tetrahydrofuran and 5 ml of water in a round-bottom flask, and lithium hydroxide (1.1 eq) was slowly added. The mixture was reacted at room temperature for 2 hours. The tetrahydrofuran was dried by spin-drying, and water and EA were added for extraction. The organic phase was removed, and the aqueous phase was adjusted to an acidic pH of 2 and then extracted with DCM to obtain the product. The organic phase was washed with saturated brine and dried over sodium sulfate to obtain 450 mg of the crude product 21-4 (yield 98%).

[0114] (3) 21-4150 mg was dissolved in 10 ml of dichloromethane in a round-bottom flask, and then triethylamine (3 eq), HOBT (1.2 eq), EDCI (1.2 eq), and 21-5 (1.1 eq) were added in sequence. The reaction was completed at room temperature overnight and directly purified by column to obtain 40 mg of compound 21 (2S, 5S) (yield 25%).

[0115] 3. Synthesis of compound 21 (2R, 5S)

[0116] (1) In a 100 mL round-bottom flask, 21-1 (0.4 g, 1.0 eq), 21-6 (1.5 eq), EDCI (1.5 eq), HOBT (1.5 eq), triethylamine (3 eq), and 10 ml of DCM were added to the flask and reacted at room temperature overnight. After the reaction, silica gel powder was added and the sample was purified by column chromatography and dried to obtain a white solid. Chiral separation was performed to obtain compound 21-7 (0.21 g, 97% purity, 40% yield).

[0117] (2) In a 100 mL round-bottom flask, 21-7 (0.210 g, 1.0 eq), LiOH (0.044 g, 3.0 eq), 10 mL of THF, and 10 mL of water were added and reacted at room temperature for 1 h. After the reaction, the THF was dried and the mixture was acidified by adding dilute hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic phase was dried by adding anhydrous sodium sulfate. The mixture was dried and dried to obtain 21-8 as a white solid (0.15 g, 97% purity, 74% yield).

[0118] (3) In a 100 mL round-bottom flask, 21-8 (0.150 g, 1.0 eq), 21-5 (0.042 g, 1.5 eq), EDCI (0.132 g, 1.5 eq), HOBT (0.093 g, 1.5 eq), triethylamine (0.140 g, 3 eq), and 10 ml of DCM were added to the flask and reacted at room temperature overnight. After the reaction, silica gel powder was added, the sample was purified by column chromatography, and dried to obtain 21(2R,5S) as a white solid (0.090 g, purity 97%, yield 51%).

[0119] 4. Synthesis of Compound 20(2R)

[0120] The preparation method of compound 20-1 refers to 21-4.

[0121] To a 100 mL round-bottom flask, 20-1 (0.120 g, 1.0 eq), 20-2 (0.026 g, 1.5 eq), EDCI (0.106 g, 1.5 eq), HOBT (0.075 g, 1.5 eq), triethylamine (0.102 g, 3 eq), and 10 ml of DCM were added and allowed to react overnight at room temperature. After the reaction, silica gel powder was added, the sample was purified by column chromatography, and dried to afford 20(2R) as a white oil (0.084 g, 93% purity, 64% yield).

[0122] 5. Synthesis of compound 68(2R)

[0123] (1) In a 100 mL round-bottom flask, 68-1 (0.400 g, 1.0 eq), 21-6 (0.145 g, 1.0 eq), EDCI (0.325 g, 1.5 eq), HOBT (0.284 g, 1.5 eq), triethylamine (0.430 g, 3 eq), and 10 ml of DCM were added to the flask and reacted at room temperature overnight. After the reaction, silica gel powder was added, the sample was purified by column chromatography, and dried to obtain 68-2 as a white solid (0.3 g, purity 97%, yield 56%).

[0124] (2) In a 100 mL round-bottom flask, 68-2 (0.240 g, 1.0 eq), LiOH (0.400 g, 2.0 eq), 10 mL of THF, and 10 mL of water were added and reacted at room temperature for 1 h. After the reaction, the THF was dried and the mixture was acidified by adding dilute hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic phase was dried by adding anhydrous sodium sulfate. The mixture was dried and dried to obtain 68-3 as a white solid (0.18 g, purity 97%, yield 80%).

[0125] (3) In a 100 mL round-bottom flask, 68-3 (0.180 g, 1.0 eq), 21-5 (0.030 g, 1.0 eq), EDCI (0.145 g, 1.5 eq), HOBT (0.102 g, 1.5 eq), triethylamine (0.155 g, 3 eq), and 10 ml of DCM were added to the flask and allowed to react overnight at room temperature. After the reaction, silica gel powder was added, the sample was purified by column chromatography, and dried to obtain 68(2R) as a white solid (0.034 g, purity 96%, yield 17%).

[0126] 6. Synthesis of compound 115 (2S, 5S)

[0127] (1) Compound 115-1 (1.0 g, 3.95 mmol) and compound 115-2 (1.1 g, 5.13 mmol) were dissolved in 30 ml of dichloromethane, triethylamine (0.8 g, 7.90 mmol) was added, and HOBT (0.8 g, 5.92 mmol) and EDCI (1.1 g, 5.92 mmol) were slowly added. The reaction was allowed to proceed at room temperature for 2 hours. LCMS monitored the reaction to be complete. The reaction solution was diluted with 30 ml of dichloromethane, and the organic phase was washed with water and saturated brine, dried, and concentrated. The residue was purified by column chromatography to obtain compound 115-3 (315 mg, yield 19%).

[0128] (2) Compound 115-3 (315 mg, 0.76 mmol) was dissolved in 5 ml of THF, and 5 ml of an aqueous solution of lithium hydroxide (64 mg, 1.52 mmol) was added at room temperature. The reaction was completed after monitoring by LCMS. Dilute hydrochloric acid was added to adjust the pH to 5, and 20 ml of water and 20 ml of EA were added for extraction. The organic phase was dried and concentrated to obtain a crude compound 115-4 (280 mg, yield 92%).

[0129] (3) Compound 115-4 (280 mg, 0.7 mmol) was dissolved in 10 ml of DMF, and compound 21-5 (68 mg, 1.4 mmol) was added. DIPEA (450 mg, 3.5 mmol) and HATU (532 mg, 1.4 mmol) were added. The mixture was stirred at room temperature for 2 hours. The reaction was monitored by LCMS until completion. The reaction solution was diluted with EA, and the organic phase was washed with water and saturated brine, dried, and concentrated. The residue was purified by column chromatography to obtain compound 115 (2S, 5S) (70 mg, yield 23%).

[0130] 7. Synthesis of compound 125 (2S, 5S)

[0131] 125-2 was prepared by referring to the preparation method of 21-8 above. 125-2 (200 mg, 0.62 mmol) was dissolved in 5 ml of dichloromethane, and triethylamine (354 mg, 1.85 mmol), EDCI (177.35 mg, 0.93 mmol), HOBT (354 mg, 0.93 mmol), and compound 125-1 (63.63 mg, 0.62 mmol) were added. The reaction was allowed to react at room temperature for 4 h. LCMS monitored the reaction to be complete. The reaction solution was diluted with water, the aqueous phase was extracted with dichloromethane, the organic phase was dried and concentrated, and the residue was purified by column chromatography (EA:PE = 1:2) to give compound 125 (2S, 5S) (160 mg, 63% yield, as a light yellow oil).

[0132] 8. Synthesis of compound 164 (2S, 5S)

[0133] (1) Compound 164-1 (7.00 g, 26.21 mmol) was dissolved in 50 ml of dichloromethane. Oxalyl chloride (3.30 mL, 39.31 mmol) and a catalytic amount of N,N-dimethylformamide were added at room temperature. The reaction was allowed to proceed for 2 h at room temperature. The reaction was complete after monitoring by LCMS. The reaction solution was concentrated and set aside. Compound 164-2 (4.39 g, 34.07 mmol) was dissolved in 40 ml of tetrahydrofuran. n-Butyllithium solution (12.58 mL, 31.45 mmol, 2.5 M / L in THF) was added dropwise at -78°C under nitrogen protection. The reaction was allowed to proceed for 1 h at -78°C. The prepared acid chloride was dissolved in 20 mL of tetrahydrofuran, added dropwise to the above system at -78°C and reacted for 2 h. The reaction was completed after monitoring by LCMS. An aqueous ammonium chloride solution was added to the reaction solution for quenching, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA:PE=1:5) to obtain compound 164-3 (2.30 g, yield 46%, white solid).

[0134] (2) Compound 164-3 (2.30 g, 6.08 mmol) was dissolved in 15 ml of tetrahydrofuran. 30% hydrogen peroxide (2.75 g, 24.30 mmol) and lithium hydroxide (0.14 g, 6.08 mmol) were added under an ice-water bath. The mixture was allowed to react at room temperature for 30 min. LCMS monitored the reaction until complete. The reaction solution was diluted with water, the aqueous phase was acidified, and extracted with ethyl acetate. The organic phase was washed with saturated brine, dried, and concentrated to afford compound 164-4 (1.6 g, 98% yield, as a white solid).

[0135] (3) Compound 164-4 (200 mg, 0.75 mmol) was dissolved in 2 ml of dichloromethane. Triethylamine (251 mg, 1.50 mmol), 19-2 hydrochloride (189 mg, 1.13 mmol), HOBT (152 mg, 1.13 mmol), and EDCI (216 mg, 1.13 mmol) were added sequentially at room temperature. The mixture was allowed to react for 3 h at room temperature. LCMS monitored the reaction to confirm completion. The reaction solution was diluted with water and ethyl acetate. The organic phase was washed with saturated aqueous ammonium chloride and saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA:PE = 1:3) to obtain compound 164 (2S, 5S) (210 mg, 73% yield, as a white solid).

[0136] 9. Synthesis of Compound 203 (2S, 5R)

[0137] (1) Compound 115-1 (160 mg, 0.63 mmol) was dissolved in 5 ml of methanol. 10% Pd / C (13 mg, 0.12 mmol) was added under nitrogen to displace the hydrogen. The mixture was allowed to react at room temperature for 2 h. LCMS monitored the reaction to completion. The reaction solution was filtered and concentrated to afford crude compound 203-1 (150 mg, 90% yield, white oil), which was used directly in the next step.

[0138] (2) Compound 203-1 (150 mg, 0.59 mmol) was dissolved in 2 ml of dichloromethane, and triethylamine (178 mg, 1.76 mmol), compound 203-2 (83 mg, 0.71 mmol), HOBT (119 mg, 0.88 mmol), and EDCI (169 mg, 0.88 mmol) were added in sequence. The mixture was allowed to react at room temperature for 2 h. LCMS monitoring confirmed the completion of the reaction. The reaction solution was diluted with water and dichloromethane, extracted with dichloromethane, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography (EA:PE = 1:1) to obtain compound 203 (2S, 5R) (74 mg, 32% yield, as a light yellow oil).

[0139] 10. Synthesis of Compound 227(2S)

[0140] (1) In a 500 mL single-necked bottle, 19-4 (12.70 g, 66.30 mmol), compound 227-1 (12.43 g, 86.19 mmol), NaHCO3 (27.85 g, 331.49 mmol) and 70 mL of isopropanol were added, the temperature was raised to 50°C with stirring, and the reaction was carried out for 2 h. LC-MS monitoring showed that the product was the main peak. The solvent was dried, and ethyl acetate and water were added for extraction. Silica gel powder was added and the sample was purified (PE / EA = 23%) to obtain 227-2 (17 g, yield 85.6%).

[0141] (2) Compound 227-2 (2.00 g, 6.68 mmol), 50 mL of DCM, and pyridine (1.06 g, 13.37 mmol) were added to a 250 ml single-necked flask and stirred for 15 min in an ice bath. Then, 227-3 (2.26 g, 8.02 mmol) was slowly added dropwise and reacted at room temperature for 2 h. The main peak of the product was detected by LC-MS. DCM and water were added for extraction. The product was dried to give 2 g of crude product 227-4 in a yield of 69.4%.

[0142] (3) Compound 227-4 (2.00 g, 4.64 mmol), 40 mL of dichloromethane and DBU (1.41 g, 9.27 mmol) were added to a 250 ml single-necked bottle and reacted at room temperature for 1 h. The main peak of the product was monitored by LC-MS. DCM and water were added for extraction. Silica gel powder was added and the sample was mixed and purified (PE / EA = 45%) to obtain product 227-5 (1.13 g, yield 86.9%).

[0143] (4) Compound 227-5 (1.13 g, 4.02 mmol) and 30 mL of THF were added to a 250 mL single-necked flask and stirred at room temperature for 10 min. A solution of lithium hydroxide (288.63 mg, 12.05 mmol) dissolved in 10 mL of water was added and the reaction was continued for 2.5 h. The main peak of the product was monitored by LC-MS. The pH of the solution was adjusted to 3-5 with hydrochloric acid. EA and water were added for extraction. Silica gel powder was added and the sample was mixed and purified (PE / EA = 50%) to obtain 227-6 (900 mg, yield 84.1%).

[0144] (5) Compound 227-6 (200 mg, 748.41 μmol), 227-7 (148.37 mg, 1.12 mmol), triethylamine (227.20 mg, 2.25 mmol), HOBT (202.26 mg, 1.50 mmol), and 20 mL of DCM were added to a 100 mL single-necked flask and stirred at room temperature for 10 min. EDCI (232.38 mg, 1.50 mmol) was added and the reaction was allowed to proceed overnight. LC-MS detected the main peak of the product. Silica gel powder was added and the sample was purified (PE / EA = 40%) to obtain compound 227(2S) (127 mg, 44.5% yield).

[0145] 11. Synthesis of compound 274 (2S, 5S)

[0146] (1) 274-1 (0.5 g, 2.64 mmol) was dissolved in 10 mL of DCM at 0°C. Triethylamine (0.534 g, 5.29 mmol), 274-2 (0.459 g, 3.16 mmol), EDCI (0.759 g, 3.96 mmol), and HOBT (0.534 g, 3.96 mmol) were added and reacted at room temperature for 4 h. The reaction was monitored by LCMS for completion. The reaction solution was quenched with saturated aqueous ammonium chloride and extracted with DCM. The organic phase was purified by column chromatography (THF / PE = 1 / 3) to afford 274-3 (700 mg, 95.8% yield) as a light yellow oil.

[0147] (2) 274-3 (700 mg, 2.5 mmol) was dissolved in 5 mL of DCM at 0°C, 1 mL of HCl / 1,4-dioxane solution was added, and the temperature was slowly raised to room temperature. The reaction was allowed to react for 2 h. LCMS monitored the reaction completion. The reaction solution was evaporated to dryness to obtain the crude product 274-4 as a light yellow oil.

[0148] (3) 164-4 (150 mg, 0.564 mmol) was dissolved in 5 mL of DCM at 0°C, and triethylamine (114 mg, 1.13 mmol), 274-4 (121 mg, 0.677 mmol), EDCI (161 mg, 0.846 mmol), and HOBT (114 mg, 0.846 mmol) were added. The mixture was allowed to react at room temperature for 4 h. The reaction was monitored by LCMS for completion. The reaction solution was quenched with saturated aqueous ammonium chloride and extracted with DCM. The organic phase was purified by column chromatography (THF / PE = 1 / 3) to afford 274 (2S, 5S) as a light yellow oil (120 mg, 50% yield).

[0149] 12. Synthesis of Compound 278 (2S, 5S)

[0150] The preparation of compound 278-1 refers to compound 21-4.

[0151] In a 50 mL single-necked flask, compound 278-1 (100 mg, 0.29 mmol) was dissolved in 1.5 mL of dichloromethane. Triethylamine (59 mg, 0.58 mmol), compound 278-2 (42 mg, 0.58 mmol), 1-hydroxybenzotriazole (HOBT, 59 mg, 0.44 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 84 mg, 0.44 mmol) were added and allowed to react at room temperature for 5 h. LCMS monitored the reaction for completion. The reaction solution was quenched with water and extracted with dichloromethane. The organic phase was washed with water, saturated ammonium chloride solution, and saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA / PE = 1 / 10) to afford compound 278 (2S, 5S) (81 mg, 71.07% yield, as a light yellow oil).

[0152] 13. Synthesis of compound 328(2S)

[0153] (1) In a 100 mL three-necked flask, compound 328-1 (1000 mg, 5.18 mmol) was dissolved in 10 mL of tetrahydrofuran, and compound 328-2 (2199 mg, 7.77 mmol) was added. The atmosphere was replaced with nitrogen three times, and lithium bis(trimethylsilyl)amide (1300 mg, 7.77 mmol) was slowly added dropwise to the reaction solution at -78°C. The reaction was incubated for 2 h. LCMS monitoring confirmed the completion of the reaction. The reaction solution was quenched with saturated ammonium chloride solution, and the insoluble matter was removed by filtration through celite. The filtrate was extracted with ethyl acetate, and the organic phase was washed with water and saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA / PE = 1 / 10) to obtain compound 328-3 (1500 mg, yield 60.84%, light yellow solid).

[0154] (2) In a 50 mL single-necked bottle, compound 328-3 (1500 mg, 3.15 mmol) was dissolved in 8 mL of N,N-dimethylformamide. 6 M hydrochloric acid (345 mg, 9.45 mmol) and saturated ammonium chloride solution (505 mg, 9.45 mmol) were added, and the mixture was allowed to react at 120°C for 20 h. LCMS monitoring confirmed the completion of the reaction. The reaction solution was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was washed with water and saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA / PE = 1 / 5) to afford compound 328-4 (200 mg, yield 20.03%) as a light yellow solid.

[0155] (3) In a 50 mL single-necked flask, compound 328-4 (200 mg, 0.63 mmol) was dissolved in 2 mL of tetrahydrofuran. A 2 mL solution of lithium hydroxide (23 mg, 0.95 mmol) was added and the mixture was allowed to react at room temperature for 1 h. LCMS monitoring confirmed the completion of the reaction. The reaction solution was adjusted to pH 2 with 1 M hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water and saturated brine, dried, and concentrated to afford compound 328-5 (150 mg, 78.58% yield, pale yellow crude product).

[0156] (4) In a 50 mL single-necked flask, compound 328-5 (150 mg, 0.49 mmol) was dissolved in 2 mL of dichloromethane. Triethylamine (99 mg, 0.98 mmol), compound 227-7 (129 mg, 0.98 mmol), 1-hydroxybenzotriazole (99 mg, 0.74 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (142 mg, 0.74 mmol) were added and reacted at room temperature for 5 h. LCMS monitoring confirmed the completion of the reaction. The reaction solution was quenched with water and extracted with dichloromethane. The organic phase was washed with water, saturated ammonium chloride solution, and saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA / PE = 1 / 10) to obtain compound 328(2S) (186 mg, yield 91.03%, light yellow oil).

[0157] 14. Synthesis of Compound 330

[0158] (1) Compound 330-1 (11.76 g, 31.80 mmol) was dissolved in 30 ml of tetrahydrofuran. NaHMDS (8.48 ml, 21.20 mmol) was added dropwise under an ice-water bath and nitrogen atmosphere, and the mixture was allowed to react at room temperature for 1 h. Compound 328-2 (3.00 g, 10.60 mmol) was dissolved in 5 ml of tetrahydrofuran and added dropwise to the reaction system under an ice-water bath. The mixture was allowed to react at room temperature for 12 h. LCMS showed that the reaction was complete. The reaction solution was quenched by adding aqueous ammonium chloride solution. The aqueous phase was extracted with ethyl acetate, and the organic phase was washed with saturated brine, dried, and concentrated. The residue was purified by column chromatography (EA / PE = 1 / 10) to obtain compound 330-2 (170 mg, 5.4% yield, yellow oil).

[0159] (2) Compound 330-2 (170 mg, 0.57 mmol) was dissolved in 3 ml of tetrahydrofuran and 1 ml of water. Lithium hydroxide (21 mg, 0.86 mmol) was added under an ice-water bath and allowed to react at room temperature for 2 h. LCMS indicated the reaction was complete. The reaction solution was diluted with water and adjusted to acidic. The aqueous phase was extracted with ethyl acetate, and the organic phase was washed with saturated brine, dried, and concentrated to afford crude product 330-3 (160 mg, yellow oil).

[0160] (3) Compound 330-3 (160 mg, 0.57 mmol) was dissolved in 2 ml of dichloromethane. Triethylamine (172 mg, 1.70 mmol), compound 227-7 (90 mg, 0.68 mmol), HOBT (115 mg, 0.85 mmol), and EDCI (163 mg, 0.85 mmol) were added in sequence and reacted at room temperature for 2 h. LCMS monitoring confirmed the completion of the reaction. The reaction solution was diluted with water and dichloromethane, extracted with dichloromethane, and the organic phase was washed with saturated ammonium chloride and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography (EA / PE = 1 / 3) to obtain compound 330 (140 mg, yield 62.5%, light yellow oil).

[0161] Biological activity evaluation:

[0162] The activity level standards for plant damage (i.e., growth control rate) are as follows:

[0163] Level 9: Complete death;

[0164] Level 8: Growth control rate is greater than or equal to 90% and less than 100%;

[0165] Level 7: Growth control rate is greater than or equal to 80% and less than 90%;

[0166] Level 6: Growth control rate is greater than or equal to 70% and less than 80%;

[0167] Level 5: Growth control rate is greater than or equal to 50% and less than 70%;

[0168] Level 4: Growth control rate is greater than or equal to 30% and less than 50%;

[0169] Level 3: Growth control rate is greater than or equal to 20% and less than 30%;

[0170] Level 2: Growth control rate is greater than or equal to 10% and less than 20%;

[0171] Level 1: Growth control rate is less than 10%;

[0172] Level 0: No effect.

[0173] The above growth control rates are fresh weight control rates.

[0174] Post-emergence test:

[0175] Monocotyledonous and dicotyledonous weed seeds, as well as staple crop seeds, were placed in plastic pots filled with soil, covered with 0.5-2 cm of soil, and grown in a well-maintained greenhouse environment. Two weeks after sowing, the test plants were treated. The test compounds of the present invention were dissolved in acetone, then Tween 80 was added. Methyl oleate emulsifiable concentrate was used as a synergist, and the solution was diluted with water to a desired concentration. The solution was then sprayed onto the plants using a spray tower. Following incubation in the greenhouse for three weeks, the weed response was assessed. Representative data are listed in Table 2.

[0176] Table 2 Post-emergence weed test results

[0177] Note: N stands for no data; Reference compound A:

[0178] Pre-emergence testing:

[0179] Monocotyledonous and dicotyledonous weed seeds, as well as staple crop seeds, were placed in plastic pots filled with soil and covered with 0.5-2 cm of soil. The test compounds of the present invention were dissolved in acetone, then diluted with Tween 80 and water to a desired concentration. The solutions were then sprayed immediately after sowing. The plants were incubated in a greenhouse for four weeks after application and observed for test results. Representative data are listed in Table 3.

[0180] Table 3 Pre-emergence weed test results

[0181] Note: N stands for no data; Reference compound A:

[0182] At the same time, through testing on major weeds in wheat and rice fields, we found that the compounds described in the present invention generally have good weed control effects. In particular, we noticed that they have extremely high activity against broad-leaved weeds and sedges that are resistant to ALS inhibitors, such as wild arrowhead, firefly rush, Cyperus diversiformis, Artemisia selengensis, Shepherd's purse, wheat bark, Gallia sinensis, and Cyperus rotundus, and have very good commercial value.

[0183] Safety evaluation of transplanted rice and evaluation of paddy field weed control effectiveness:

[0184] After filling a 1 / 1,000,000-hectare tank with paddy field soil, seeds of barnyard grass, firefly rush, and wolfsbane are sown and lightly covered with soil. The tank is then placed in a greenhouse with water at a depth of 0.5-1 cm. The next day or two days later, tubers of wild arrowhead are implanted. The tank is then maintained at a depth of 3-4 cm. When barnyard grass, firefly rush, and wolfsbane reach the 0.5-leaf stage, and when wild arrowhead reaches the primary leaf stage, a wettable powder or suspension prepared according to conventional formulation methods is evenly applied using a pipette to achieve the desired active ingredient dosage.

[0185] Separately, paddy field soil was filled into 1 / 1,000,000 hectare pots and leveled to a water depth of 3-4 cm. The next day, three-leaf rice (japonica rice) was transplanted at a transplanting depth of 3 cm. Five days after transplanting, the compound of the present invention was treated in the same manner as above.

[0186] The growth status of barnyard grass, firefly rush, wolf grass and wild arrowhead were observed with the naked eye on the 14th day after treatment, and the growth status of rice on the 21st day after treatment. The effects were evaluated based on the above-mentioned activity standard levels. Many compounds showed excellent activity and selectivity.

[0187] Note: Seeds of Echinochloa crusgalli, Echinochloa crusgalli, and Lycopodium album were collected from Heilongjiang, China, and were found to be resistant to conventional doses of pyrazosulfuron-methyl.

[0188] Extensive testing has also revealed that many of the compounds and compositions described herein exhibit excellent selectivity against grassy lawns, including zoysia, bermudagrass, tall fescue, bluegrass, ryegrass, and seashore paspalum, controlling many key grass and broadleaf weeds. Tests on sugarcane, soybeans, cotton, sunflower, potatoes, fruit trees, and vegetables, under different application methods, have also demonstrated excellent selectivity and commercial value.

[0189] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not limiting. Although the present invention has been described in detail with reference to the preferred embodiments, those skilled in the art should understand that the technical solutions of the present invention may be modified or replaced by equivalents without departing from the spirit and scope of the technical solutions of the present invention.

Claims

1. An isoxazoline compound or a salt thereof, as shown in General Formula I: Among them, X is an aryl or a heterocyclic group; Y is a halogen, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylalkyl group, a cycloalkenyl group, a cycloalkenylalkyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group, -OR, -SR, -alkylene-OR, -alkylene-O(CO)R, -alkylene-SR, -(CO)OR or -(CO)R; Z is hydrogen, a halogen, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylalkyl group, a cycloalkenyl group, a cycloalkenylalkyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group, a cyanoalkyl group, -OR, -SR, -N(R)2, -alkylene-OR, -alkylene-SR, -alkylene-N(R)2, -(CO)OR, -alkylene-(CO)OR, -alkylene-(CO)N(R)2, -(CO)N(R)2, an aryl group, a heterocyclic group, an arylalkyl group or a heterocyclicalkyl group; R1 is hydrogen, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, -alkylene-OR, -alkylene-SR, -alkylene-(SO)R, -alkylene-(SO)2R, -alkylene-(CO)OR, -alkylene-(CO)N(R)2, -alkylene-(CO)NR(OR), -alkylene-O-N=C(R)2, -alkylene-(CO)O-N=C(R)2, an aryl group, a heterocyclic group, or an alkyl group, alkenyl group or alkynyl group substituted by at least one group selected from a halogen, a cycloalkyl group, a cycloalkenyl group, a heterocyclic group or an aryl group; R2 is hydrogen, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylalkyl group, a cycloalkenyl group, a cycloalkenylalkyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group, an aryl group, a heterocyclic group, an arylalkyl group, a heterocyclicalkyl group, -alkylene-OR, -alkylene-SR, a cyanoalkyl group, -(CO)OR, -SO2R or -SO2N(R)2; or R1 and R2 together form -(CH2) which is unsubstituted or substituted by at least one group selected from alkyl, halogen or oxo n -; n is 3, 4 or 5; R3 is O, NH or N-alkyl; Q1 and Q2 are each independently O or S; The aforementioned cycloalkyl group, cycloalkenyl group, aryl group or heterocyclic group is optionally substituted by at least one group selected from an oxo group, a halogen, a cyano group, a nitro group, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylalkyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group, -OR, -SR, -alkylene-OR, -alkylene-SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, -SO2R, -OSO2R, -N(R)2 or -NR(OR); R independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl substituted by at least one group selected from halogen, hydroxy, alkoxy, cyano, trialkylsilyl, phenyl or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, heterocyclic group, or phenyl or heterocyclic group substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, haloalkoxy, phenyl or halophenyl; or N(R)2 together form 2. An isoxazoline compound or a salt thereof according to claim 1, wherein: Y is a halogen, a cyano group, a C1-C8 alkyl group, a C2-C8 alkenyl group, a C2-C8 alkynyl group, a C3-C8 cycloalkyl group, a C3-C8 cycloalkyl C1-C8 alkyl group, a C3-C8 cycloalkenyl group, a C3-C8 cycloalkenyl C1-C8 alkyl group, a halo C1-C8 alkyl group, a halo C2-C8 alkenyl group, a halo C2-C8 alkynyl group, -OR, -SR, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-O(CO)R, -(C1-C8 alkylene)-SR, -(CO)OR or -(CO)R; Z is hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, cyano C1-C8 alkyl, -OR, -SR, -N(R)2, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, -(C1-C8 alkylene)-N(R)2, -(CO)OR, -(C1-C8 alkylene)-(CO)OR, -(C1-C8 alkylene)-(CO)N(R)2, -(CO)N(R)2, aryl, heterocyclic group, aryl C1-C8 alkyl or heterocyclic group C1-C8 alkyl; R1 is hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, -(C1-C8 alkylene)-(SO)R, -(C1-C8 alkylene)-(SO)2R, -(C1-C8 alkylene)-(CO)OR, -(C1-C8 alkylene)-(CO)N(R)2, -(C1-C8 alkylene)-(CO)NR(OR), -(C1-C8 alkylene)-O-N=C(R)2, -(C1-C8 alkylene)-(CO)O-N=C(R)2, aryl, heterocyclic group, or C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted by at least one group selected from halogen, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic group or aryl; R2 is hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, aryl, heterocyclic group, aryl C1-C8 alkyl, heterocyclic group C1-C8 alkyl, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, cyano C1-C8 alkyl, -(CO)OR, -SO2R or -SO2N(R)2; or R1 and R2 together form -(CH2)n which is unsubstituted or substituted by at least one group selected from C1-C8 alkyl, halogen or oxo; n is 3, 4 or 5; R3 is O, NH or N-(C1-C8 alkyl); The foregoing C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl or heterocyclic group is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, -OR, -SR, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, -SO2R, -OSO2R, -N(R)2 or -NR(OR); R independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted by at least one group selected from halogen, hydroxy, C1-C8 alkoxy, cyano, tri-C1-C8 alkylsilyl, phenyl or C1-C8 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl, heterocyclic group, or phenyl or heterocyclic group substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, halo-C1-C8 alkoxy, phenyl or halo-phenyl; or N(R)2 together form 3. An isoxazoline compound or a salt thereof according to claim 1 or 2, characterized in that: Y is halogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, -OR, -SR, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-O(CO)R, -(C1-C6 alkylene)-SR, -(CO)OR or -(CO)R; Z is hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, cyano C1-C6 alkyl, -OR, -SR, -N(R)2, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-SR, -(C1-C6 alkylene)-N(R)2, -(CO)OR, -(C1-C6 alkylene)-(CO)OR, -(C1-C6 alkylene)-(CO)N(R)2, -(CO)N(R)2, aryl, heterocyclic group, aryl C1-C6 alkyl or heterocyclic group C1-C6 alkyl; R1 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-SR, -(C1-C6 alkylene)-(SO)R, -(C1-C6 alkylene)-(SO)2R, -(C1-C6 alkylene)-(CO)OR, -(C1-C6 alkylene)-(CO)N(R)2, -(C1-C6 alkylene)-(CO)NR(OR), -(C1-C6 alkylene)-O-N=C(R)2, -(C1-C6 alkylene)-(CO)O-N=C(R)2, aryl, heterocyclic group, or C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl substituted by at least one group selected from halogen, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic group or aryl; R2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, aryl, heterocyclic group, aryl C1-C6 alkyl, heterocyclic group C1-C6 alkyl, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-SR, cyano C1-C6 alkyl, -(CO)OR, -SO2R or -SO2N(R)2; or R1 and R2 together form -(CH2) which is unsubstituted or substituted by at least one group selected from C1-C6 alkyl, halogen or oxo n -; n is 3, 4 or 5; R3 is O, NH or N-(C1-C6 alkyl); The aforementioned C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl or heterocyclic group is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, -OR, -SR, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, -SO2R, -OSO2R, -N(R)2 or -NR(OR); R independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl substituted by at least one group selected from halogen, hydroxy, C1-C6 alkoxy, cyano, tri-C1-C6 alkylsilyl, phenyl or C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl, heterocyclic group, or phenyl or heterocyclic group substituted by at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, phenyl or halogenated phenyl; or N(R)2 together form Preferably, the compound is selected from any one of Tables 1, A-H in the specification.

4. A chiral - center - containing isoxazoline compound of formula I' or a salt thereof: Among them, The carbon atom (C*) at positions 2 and / or 5 is a chiral center, and the substituents R1, R2, R3, Q1, Q2, X, Y and Z are defined as described in any one of claims 1-3, and Z is not hydrogen; Based on the content of stereoisomers with R and S configurations at position 2, it has a stereochemical purity of 60 - 100% (S), preferably 70 - 100% (S), more preferably 80 - 100% (S), further preferably 90 - 100% (S), still further preferably 95 - 100% (S); or it has a stereochemical purity of 60 - 100% (R), preferably 70 - 100% (R), more preferably 80 - 100% (R), further preferably 90 - 100% (R), still further preferably 95 - 100% (R); and / or based on the carbon atom at position 5 being 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% (S), preferably 70 - 100% (S), more preferably 80 - 100% (S), further preferably 90 - 100% (S), still further preferably 95 - 100% (S); or it has a stereochemical purity of 60 - 100% (R), preferably 70 - 100% (R), more preferably 80 - 100% (R), further preferably 90 - 100% (R), still further preferably 95 - 100% (R).

5. A method for preparing an isoxazoline compound or a salt thereof according to any one of claims 1-4, characterized in that, Comprising the following steps: (1) React the compound represented by General Formula II with the compound represented by General Formula III or its salt to obtain the compound represented by General Formula I. The reaction equation is as follows: Or (2) reacting the compound represented by the general formula IV with the compound represented by the general formula V or a salt thereof to obtain the compound represented by the general formula I, and the reaction equation is as follows: Or (3) reacting the compound represented by the general formula VI with the compound represented by the general formula VII to obtain the compound represented by the general formula I, and the reaction equation is as follows: wherein, M and M1 independently represent OH or halogen respectively, Hal represents halogen, and the substituents R1, R2, R3, Q1, Q2, X, Y and Z are defined as described in any one of claims 1 - 4; Preferably, the reactions (1) and (2) are respectively carried out in the presence of a solvent; more preferably, a base and / or a condensing agent are added during the reaction process; further preferably, the base is selected from at least one of inorganic bases or organic bases; the condensing agent is selected from at least one of Py - BOP, Py - AOP, EDCI, HOBT, DCC, HBTU or HATU; the solvent is selected from at least one of DMF, DMA, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran or ethyl acetate; Preferably, the reaction (3) is carried out in the presence of a base and a solvent; more preferably, the base is selected from at least one of inorganic bases or organic bases; the solvent is selected from at least one of methanol, ethanol, isopropanol, DMF, DMA, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran or ethyl acetate.

6. An intermediate as described in formula II, formula III, formula V or formula VI of claim 5.

7. A herbicide composition, characterized in that, Comprising at least one of the isoxazoline compounds or their salts described in any one of claims 1 - 4 in a herbicidally effective amount; preferably, formulation adjuvants are further included; more preferably, other active ingredients are further included.

8. A method for controlling weeds, characterized in that, Comprising applying at least one of the isoxazoline compounds or their salts described in any one of claims 1 - 4 in a herbicidally effective amount or the herbicide composition described in claim 7 to plants or weed areas.

9. Use of at least one of the isoxazoline compounds or salts thereof according to any one of claims 1-4 or the herbicide composition according to claim 7 for controlling weeds. Preferably, the isoxazoline compound or its salt is used for controlling weeds in useful crops, and the useful crops are genetically modified crops or crops treated with genome editing techniques.