Aromatic compound containing substituted isoxazoline and preparation method, herbicidal composition and application thereof

Abstract

The application belongs to the technical field of pesticides, and particularly relates to a substituted isoxazoline-containing aromatic compound, a preparation method, a herbicidal composition and application thereof. The compound is shown in the general formula I: wherein Q represents Y represents halogen, halogenated alkyl or cyano; Z represents halogen; X1 and X2 independently represent hydrogen, halogen, alkyl or the like; X3 represents halogen, cyano or the like; X4 independently represents -COOR5 or -alkyl-COOR5; and R5 independently represents hydrogen, alkyl or the like. The compound has excellent herbicidal activity on gramineous weeds, broadleaf weeds and the like, and has high selectivity on crops even at a low application rate.

Description

[0001] This application is a divisional application of Chinese Patent Application No. 202011215664.1, filed on November 4, 2020, entitled "An aromatic compound containing substituted isoxazoline and its preparation method, herbicidal composition and application". Technical Field

[0002] This invention belongs to the field of pesticide technology, specifically relating to an aromatic compound containing substituted isoxazoline, its preparation method, herbicidal composition, and application. Background Technology

[0003] Weed control is a crucial aspect of achieving efficient agriculture. Although a variety of herbicides are available on the market—for example, patent WO00 / 50409 discloses the use of the general formula compound 1-aryl-4-thiotriazine as a herbicide; CN105753853A discloses a uracil compound containing isoxazoline and its use as a herbicide—the weeding performance and crop selectivity of these known compounds are not entirely satisfactory. Furthermore, due to the expanding market, weed resistance, herbicide lifespan, economic considerations, and increasing environmental awareness, scientists need to continuously research and develop new, efficient, safe, economical herbicides with different modes of action. Summary of the Invention

[0004] This invention provides an aromatic compound containing substituted isoxazoline, its preparation method, herbicidal composition, and application. The compound exhibits excellent herbicidal activity against grass weeds and broadleaf weeds even at low application rates, and is highly selective for crops.

[0005] The technical solution adopted in this invention is as follows:

[0006] An aromatic compound containing a substituted isoxazoline, as shown in general formula I:

[0007]

[0008] Where Q represents

[0009] Y represents halogen, haloalkyl, or cyano;

[0010] Z represents halogen;

[0011] Q1, Q2, Q3, Q4, and Q5 each independently represent O or S;

[0012] R1, R2, and R6 independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl;

[0013] R7 and R8 independently represent hydrogen, alkyl, halogen, haloalkyl, or amino, respectively;

[0014] X1 and X2 independently represent hydrogen, halogen, alkyl, alkenyl, ynyl, cycloalkyl, cycloalkylalkyl, -OR3, -(CO)OR3 or phenyl, wherein the "alkyl", "alkenyl", "ynyl", "cycloalkyl" or "cycloalkylalkyl" is independently unsubstituted or substituted by at least one group selected from halogens;

[0015] X3 represents halogen, cyano, formyl, alkyl, alkenyl, ynyl, cycloalkyl, cycloalkylalkyl, -OR3, -(CO)OR3, -SR3, heterocyclic, heterocyclic alkyl, aryl, arylalkyl, or amino, and X3 does not represent methyl.

[0016] The "alkyl", "alkenyl", or "alkynyl" groups are independently unsubstituted or substituted by at least one group selected from halogen, cyano, -OR3, -(CO)R3, -SR3, -(SO2)R3, -O(CO)R3, -O-(SO2)R3, -(CO)OR3, -O(CO)OR3, -O-alkyl-(CO)OR3, or -O(CO)(CO)OR3.

[0017] The terms "cycloalkyl", "cycloalkylalkyl", "heterocyclic", "heterocyclic alkyl", "aryl", or "arylalkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR4, -SR4, -(CO)OR4, -(SO2)R4, or -N(R4)2.

[0018] The "amino" group is either unsubstituted or substituted with one or two groups selected from -R3;

[0019] X4 can represent either -COOR5 or -alkyl-COOR5 independently;

[0020] R3 can independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl;

[0021] R4 can represent hydrogen, alkyl, or haloalkyl independently;

[0022] R5 independently represents hydrogen, alkyl, alkenyl, ynyl, cycloalkyl, or cycloalkylalkyl, wherein the "alkyl", "alkenyl", "ynyl", "cycloalkyl", or "cycloalkylalkyl" is independently unsubstituted or substituted by at least one group selected from halogens.

[0023] Preferably, Y represents a halogen, a halogenated C1-C8 alkyl group, or a cyano group;

[0024] R1, R2, and R6 independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl / C1-C8 alkyl, respectively;

[0025] R7 and R8 independently represent hydrogen, C1-C8 alkyl, halogen, halogenated C1-C8 alkyl, or amino, respectively;

[0026] X1 and X2 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, -OR3, -(CO)OR3 or phenyl, wherein the "C1-C8 alkyl", "C2-C8 alkenyl", "C2-C8 ynyl", "C3-C8 cycloalkyl" or "C3-C8 cycloalkylC1-C8 alkyl" are independently unsubstituted or substituted by at least one group selected from halogens;

[0027] X3 represents halogen, cyano, formyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, -OR3, -(CO)OR3, -SR3, heterocyclic, heterocyclic C1-C8 alkyl, aryl, aryl C1-C8 alkyl, or amino, wherein...

[0028] The "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" groups are independently unsubstituted or substituted by at least one group selected from halogen, cyano, -OR3, -(CO)R3, -SR3, -(SO2)R3, -O(CO)R3, -O-(SO2)R3, -(CO)OR3, -O(CO)OR3, -O-(C1-C8 alkyl)-(CO)OR3 or -O(CO)(CO)OR3.

[0029] The "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "heterocyclic", "heterocyclic C1-C8 alkyl", "aryl", or "aryl C1-C8 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 ynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR4, -SR4, -(CO)OR4, -(SO2)R4, or -N(R4)2.

[0030] The "amino" group is either unsubstituted or substituted with one or two groups selected from -R3;

[0031] X4 can independently represent -COOR5 or -(C1-C8 alkyl)-COOR5;

[0032] R3 can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl-C1-C8 alkyl.

[0033] R4 can independently represent hydrogen, C1-C8 alkyl, or halo-C1-C8 alkyl;

[0034] R5 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl-C1-C8 alkyl, wherein each of the “C1-C8 alkyl”, “C2-C8 alkenyl”, “C2-C8 ynyl”, “C3-C8 cycloalkyl”, or “C3-C8 cycloalkyl-C1-C8 alkyl” is independently unsubstituted or substituted by at least one group selected from halogens.

[0035] More preferably, Y represents a halogen, a halogenated C1-C6 alkyl group, or a cyano group;

[0036] R1, R2, and R6 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl / C1-C6 alkyl, respectively.

[0037] R7 and R8 independently represent hydrogen, C1-C6 alkyl, halogen, halogenated C1-C6 alkyl, or amino, respectively;

[0038] X1 and X2 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, -OR3, -(CO)OR3 or phenyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", "C2-C6 ynyl", "C3-C6 cycloalkyl" or "C3-C6 cycloalkylC1-C6 alkyl" are independently unsubstituted or substituted by at least one group selected from halogens;

[0039] X3 represents halogen, cyano, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, -OR3, -(CO)OR3, -SR3, heterocyclic, heterocyclic-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, or amino, wherein...

[0040] The "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" groups are independently unsubstituted or substituted by at least one group selected from halogen, cyano, -OR3, -(CO)R3, -SR3, -(SO2)R3, -O(CO)R3, -O-(SO2)R3, -(CO)OR3, -O(CO)OR3, -O-(C1-C6 alkyl)-(CO)OR3 or -O(CO)(CO)OR3.

[0041] The "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "heterocyclic", "heterocyclic C1-C6 alkyl", "aryl", or "aryl C1-C6 alkyl" are each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR4, -SR4, -(CO)OR4, -(SO2)R4, or -N(R4)2.

[0042] The "amino" group is either unsubstituted or substituted with one or two groups selected from -R3;

[0043] X4 can independently represent -COOR5 or -(C1-C6 alkyl)-COOR5;

[0044] R3 can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C6 alkyl.

[0045] R4 can independently represent hydrogen, C1-C6 alkyl, or halo-C1-C6 alkyl;

[0046] R5 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C6 alkyl, wherein each of the “C1-C6 alkyl”, “C2-C6 alkenyl”, “C2-C6 ynyl”, “C3-C6 cycloalkyl”, or “C3-C6 cycloalkyl-C1-C6 alkyl” is independently unsubstituted or substituted by at least one group selected from halogens.

[0047] More preferably, Y represents halogen;

[0048] R1, R2, and R6 each independently represent C1-C6 alkyl groups;

[0049] R7 and R8 each independently represent hydrogen or a halogenated C1-C6 alkyl group;

[0050] X1 and X2 each independently represent hydrogen;

[0051] X3 represents halogen, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C3 alkyl, -OR3, phenyl, or benzyl, wherein...

[0052] The "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl" groups are independently unsubstituted or substituted by one, two, or three groups selected from halogen, -OR3, -O(CO)R3, -(CO)OR3, -O-(C1-C3 alkyl)-(CO)OR3, or -O(CO)(CO)OR3.

[0053] The “C3-C6 cycloalkyl”, “C3-C6 cycloalkylC1-C3 alkyl”, “phenyl” or “benzyl” are independently unsubstituted or substituted by one, two or three groups selected from halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR4 or -(CO)OR4;

[0054] X4 independently represents -COOR5;

[0055] R3 can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl / C1-C3 alkyl.

[0056] R4 can independently represent hydrogen, C1-C6 alkyl, or halo-C1-C6 alkyl;

[0057] R5 can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl.

[0058] More preferably, Y represents chlorine;

[0059] Z stands for fluorine;

[0060] R7 represents a halogenated C1-C6 alkyl group;

[0061] R8 represents hydrogen;

[0062] X3 represents halogen, formyl, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, -OR3, -(C1-C3 alkyl)-OR3, -(C1-C3 alkyl)-O(CO)R3, -(C1-C3 alkyl)-(CO)OR3, -(C1-C3 alkyl)-O-(C1-C3 alkyl)-(CO)OR3, -(C1-C3 alkyl)-O(CO)(CO)OR3, phenyl, or benzyl, wherein,

[0063] The “C1-C6 alkyl” are each independently unsubstituted or substituted by one, two or three groups selected from halogens;

[0064] R3 can independently represent hydrogen or C1-C6 alkyl groups;

[0065] R5 can represent either hydrogen or C1-C6 alkyl groups.

[0066] More preferably, Q represents

[0067] In the definitions of compounds shown in the above general formulas and in all the following structural formulas, the technical terms used, whether alone or in compound terms, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chain or branched. For example, the compound term "-alkyl-(CO)OR". 11 The alkyl group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group is, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, the alkenyl group is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl. Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl group having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein the double bond can be in any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0068] Unless otherwise specified, the term "aryl" in this invention includes, but is not limited to, phenyl, naphthyl, and... The "heterocyclic group" includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups.

[0069] And, including but not limited to, heteroaryl groups, i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms and optionally fused with benzo[a] rings, wherein 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms are selected from oxygen, nitrogen, and sulfur, for example

[0070] If a group is substituted by another group, this should be understood to mean that the group is substituted by one or more identical or different groups selected from those groups mentioned. Furthermore, the identical or different substitution characters contained in the identical or different substituents are chosen independently and may be identical or different. This also applies to ring systems formed from different atoms and units. Meanwhile, the scope of the claims excludes compounds that are chemically unstable under standard conditions, as known to those skilled in the art.

[0071] Furthermore, unless otherwise specified, the phrase "replaced by at least one group" in this invention refers to being replaced by, for example, 1, 2, 3, 4, or 5 groups; groups without specific attachment positions (including heterocyclic groups, aryl groups, etc.) can be attached at any position, including positions attached to C or N; if it is substituted, the substituent can also be substituted at any position, as long as it conforms to the rules of chemical bond attachment. For example, a heteroaryl group substituted by one methyl group. Can represent wait.

[0072] It should be noted that when general formula I When the carbon atom (C*) bonded to X3 and X4 is a chiral center (i.e., X3 and X4 are not the same), it has an R configuration or an S configuration, preferably an S configuration. 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), and even more preferably 95-100% (S). Here, "stereochemical purity" refers to the percentage of the amount of the stereoisomer relative to the total amount of stereoisomers that generate the chiral center.

[0073] Furthermore, the present invention also provides an aromatic compound containing a substituted isoxazoline with an S configuration, as shown in general formula I':

[0074]

[0075] Wherein, X3' represents hydrogen, methyl or X3, and the substituents X1, X2, X3, X4, Q, Y and Z are defined as described above, and X3 and X4 are different.

[0076] In this invention, the stereochemical configuration at the position marked * in Formulas I and I' is determined to be predominant (S) according to the Cahn-Ingold-Prelog system; however, the subject matter of this invention also relates to all stereoisomers at other positions included in Formulas I and I', and mixtures thereof. Such Formulas I and I' compounds contain, for example, one or more additional asymmetric carbon atoms or other double bonds not specifically described in Formulas I and I'. It should be understood that this invention includes pure isomers and mixtures thereof enriched to varying degrees with pure isomers, wherein the asymmetric carbon atom at the position marked * is in the S-configuration, or in the mixture, the compound or a compound with the same chemical structure has the S-configuration at the position marked *, or is present in a proportion predominantly of the compound having the S-configuration (at least 60% S-configuration), while other asymmetric carbon atoms may be present in a racemic form or may be resolved to varying degrees. Possible stereoisomers defined by a specific spatial form, such as enantiomers, diastereomers, Z- and E-isomers, are included in Formulas I and I', provided that the stereochemical configuration conditions at the position marked * are met. They can be obtained from mixtures of stereoisomers by conventional methods or prepared by stereoselective reactions in conjunction with stereochemically pure initial substances.

[0077] If various functional groups are present, the present invention also includes any ketone and enol tautomer forms, mixtures thereof, and salts thereof.

[0078] Stereoisomers can be obtained from mixtures prepared by optical resolution. Similarly, stereoisomers can be selectively prepared using stereoselective reactions and optically active starting materials and / or auxiliaries. For optical resolution, conventional methods (see Textbooks of Stereochemistry) can generally be used, such as physical methods for resolving mixtures into diastereomers, including crystallization, chromatography, especially column chromatography and high-performance liquid chromatography, distillation under reduced pressure as needed, extraction, and other methods, typically employing chromatographic separation on a chiral solid phase, which can separate the residual mixture of enantiomers. Suitable for preparative or industrial scales are methods such as crystallizing diastereomers, which can be obtained from the compound using optically active acids, and, if acidic groups are present, using optically active bases as needed.

[0079] The method for preparing the aromatic compound containing substituted isoxazoline includes the following steps:

[0080] When Q represents (1) When the compound shown in general formula II-1 is subjected to a cyclization reaction with the compound shown in general formula III-1, the compound shown in general formula I-1 is obtained, and the chemical reaction equation is as follows:

[0081]

[0082] When Q represents (2) When the compound shown in general formula II-2 is subjected to a cyclization reaction with the compound shown in general formula III-2, a compound shown in general formula I-2 is obtained, and the chemical reaction equation is as follows:

[0083]

[0084] (3) React the compound shown in general formula II-3 with the compound shown in general formula III-3 to obtain the compound shown in general formula I-3;

[0085]

[0086] (4) React the compound shown in general formula II-4 with the compound shown in general formula III-4 to obtain the compound shown in general formula I-4;

[0087]

[0088] Alternatively, (5) the compound shown in general formula I-5 is reacted with R6'-Hal via a substitution reaction to obtain the compound shown in general formula I-6;

[0089] The chemical reaction equation is as follows:

[0090]

[0091] Wherein, L1, L2, L3, L4, L5, L6 and L7 independently represent C1-C6 alkyl or aryl groups, preferably methyl, ethyl or phenyl; Hal represents a halogen, preferably iodine; R6' represents a group other than hydrogen in R6; the definitions of other substituents R1, R2, R6, R7, R8, X1, X2, X3, X4, Q1, Q2, Q3, Q4, Q5, Y and Z are as described above.

[0092] Preferably, steps (1), (2), (4) and (5) are all carried out in the presence of alkali and solvent.

[0093] The base is selected from at least one of inorganic bases (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, etc.) or organic bases (such as pyrazole, triethylamine, DIEA, etc.).

[0094] The solvent is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, or ethyl acetate.

[0095] Preferably, step (3) is performed in the presence of an acid.

[0096] The acid is selected from acetic acid, hydrochloric acid, or sulfuric acid.

[0097] Additionally, when Q When at least one of the substituents Q1, Q2, and Q3 is S, or at least one of Q4 and Q5 is S, it can also be represented by the corresponding Q. The compound used as a raw material in Lawson's reagent It can also be prepared by conventional sulfur substitution reaction in the presence of phosphorus pentasulfide.

[0098] The compounds described in this invention were also prepared using the methods described in patents WO00 / 50409 and CN105753853A.

[0099] A herbicide composition comprising at least one of the herbicidal aromatic compounds containing substituted isoxazoline, preferably further comprising a formulation adjuvant.

[0100] A method for controlling weeds, comprising applying a herbicidal effective amount of at least one of the said aromatic compounds containing substituted isoxazoline or the said herbicide composition to plants or weedy areas.

[0101] The use of at least one of the substituted isoxazoline aromatic compounds or the herbicide composition in weed control, preferably, the use of the substituted isoxazoline aromatic compounds in controlling weeds in useful crops, said useful crops being transgenic crops or crops treated with genome editing technology.

[0102] For many economically important monocotyledonous and dicotyledonous pests, the compounds of formula I and formula I' of this invention exhibit outstanding herbicidal activity. The active substances of this invention are also effective against perennial weeds that grow from rhizomes, stems, or other perennial organs and are difficult to control. In this regard, it is generally not important whether the substance is used before sowing, before germination, or after germination. Representative examples of monocotyledonous and dicotyledonous weed populations that can be controlled by the compounds of this invention are specifically mentioned, without limiting the specific species. Examples of weed species to which the active substances are effective include monocotyledons: annuals of *Oat*, *Rye*, *Grass*, *Alopecurus*, *Fararis*, *Barnyardgrass*, *Digitaria*, *Setaria*, and *Sedge*, and perennials of *Agrostis*, *Bermudagrass*, *Imperata*, and *Sorghum*, as well as perennials of *Sedge*.

[0103] Regarding dicotyledonous weed species, its effects can be extended to annual species such as *Galium aparine*, *Viola*, *Veronica*, *Sesamum indicum*, *Stellaria*, *Amaranthus*, *Sinapis*, *Ipomoea*, *Heliotropium*, *Chaenomeles*, and *Abutilon*, and perennial weeds such as *Convolvulus*, *Thistle*, *Rumex*, and *Artemisia*. The active substances of this invention effectively control harmful plants such as barnyard grass, *Sagittaria*, *Alisma*, *Eupatorium*, *Sedum*, and *Sedge* under the undetermined condition of rice sowing. If the compounds of this invention are applied to the soil surface before germination, weed seedlings can be completely prevented before they emerge, or growth can be stopped when the weeds develop cotyledons, eventually leading to their complete death after three to four weeks. The compounds of this invention exhibit particularly excellent activity against the following plants: *Apira*, *Sesamum indicum*, *Polygonum cuspidatum*, *Stellaria*, *Veronica ivy*, *Veronica arabiculata*, *Viola tricolor* and *Amaranthus*, *Galium aparine*, and *Kochia scoparia*.

[0104] While the compounds of this invention exhibit excellent herbicidal activity against both monocot and dicot weeds, they cause little to no damage to important economic crops 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, especially wheat. Therefore, the compounds of this invention are highly suitable for the selective control of unwanted plants in agricultural or ornamental crops.

[0105] Due to their herbicidal properties, these active substances can be used to control harmful plants in known or future genetically engineered plant cultivation. Transgenic plants typically possess superior traits, such as resistance to specific insecticides, particularly specific herbicides, and resistance to plant diseases or pathogenic microorganisms, such as specific insects or fungi, bacteria, or viruses. Other specific traits relate to conditions such as quantity, quality, storage stability, composition, and special components of the product. Thus, it is known that transgenic plant products have increased starch content or improved starch quality or different fatty acid compositions.

[0106] The compounds of formula I and I' or their salts are preferably used in the cultivation of economically important genetically modified crops and ornamental plants, such as cereals like 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 and I' are preferably used as herbicides for cultivating useful plants that are resistant or have been genetically engineered to resist the toxic effects of the herbicides.

[0107] Traditional methods for breeding plants with improved morphology compared to known plants include, for example, conventional mating methods and mutant breeding. In other words, new plants with improved traits can be obtained using genetic engineering methods (see, for example, EP-0221044A, EP-0131624A). Several methods have been described, for example:

[0108] - To improve starch synthesis in plants, genetic engineering is used to modify crop plants (e.g., WO 92 / 11376, WO92 / 14827, WO 91 / 19806);

[0109] - Transgenic crop plants resistant to specific herbicides, such as glufosinate-methyl (e.g., EP-0242236A, EP-0242246A), glyphosate-based herbicides (WO 92 / 00377), or sulfonylurea herbicides (EP-0257993A, US-5013659A);

[0110] - For example, genetically modified cotton plants can produce Bt toxins, which can defend against certain pests (EP-0142924A, EP-0193259A).

[0111] - A genetically modified crop plant with improved fatty acid composition (WO91 / 13972).

[0112] Many molecular biotechnologies for preparing transgenic plants with improved traits are known (see, for example, Sambrook et al., 1989, Molecular Amplification, Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory, Cold Spring Harbor, New York; or Winnacker, “Gene and Cloning,” VCH Weinheim, 2nd ed., 1996; or Christou, “Trends in Plant Science,” 1 (1996) 423-431). To perform genetic engineering operations, nucleic acid molecules may be introduced into plasmids, resulting in mutations or sequence alterations through DNA sequence recombination. Using standard methods, such as exchanging substrates, removing portions of the sequence, or adding natural or synthetic sequences, can be employed. To link DNA fragments together, it is possible to attach conjugates or linkers to the fragments.

[0113] Plant cells containing reduced-activity gene products can be prepared by methods such as expressing at least one appropriate antisense RNA or sense RNA to achieve co-inhibition, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the aforementioned gene product.

[0114] For this purpose, it is possible to use a DNA molecule containing the entire coding sequence of the gene product, including any possible flanking sequences, or a DNA molecule containing only a portion of the coding sequence, which must be long enough to achieve an antisense effect in the cell. Alternatively, a sequence that is highly homologous to but not identical to the coding sequence of the gene product can also be used.

[0115] When nucleic acid molecules are expressed in plants, the synthesized proteins can be localized in any desired plant cell compartment. However, to localize in a specific compartment, it is possible, for example, to link the coding region to a DNA sequence to ensure localization at a specific location. 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 85 (1988), 846-850; Sonnewald et al. Plant J.1 (1991), 95-106).

[0116] Using known techniques, transgenic plant cells can be recombined into the entire plant. Transgenic plants can be any desired plant variety, i.e., monocots and dicots. 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 (=external) genes or gene sequences.

[0117] When the active substances of this invention are used on genetically modified crops, in addition to the inhibitory effect on harmful plants observed in other crops, they often exhibit specific effects on the corresponding genetically modified crops. For example, they can improve or expand the range of weed control, improve the application rate, preferably combine the herbicide resistance of the genetically modified crop with the performance of the herbicide, and affect the growth and yield of the genetically modified crop. Therefore, this invention also provides the use of the compounds as herbicides to control harmful plants in genetically modified crop plants.

[0118] Furthermore, the compounds of this invention can significantly regulate crop growth. By modulating plant metabolism, these compounds can be used to directionally control plant components and promote harvesting, for example, by causing plant drying and dwarfing. They are also suitable for regulating and inhibiting unwanted plant growth without disrupting crop growth. Inhibiting plant growth plays a crucial role in many monocot and dicot crops because it can reduce or completely prevent lodging.

[0119] The compounds of the present invention can be applied using common formulations, including wettable powders, concentrated emulsions, sprayable solutions, powders, or granules. Thus, the present invention also provides herbicide compositions comprising compounds of formulas I and I'. Compounds of formulas I and I' can be formulated in various ways depending on typical biological and / or chemical physical parameters. Examples of suitable formulation choices include: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, concentrated emulsions (EC), emulsions such as oil dispersed in water and water dispersed in oil (EW), sprayable solutions, suspension concentrates (SC), dispersible oil suspensions (OD), suspensions diluted with oil or water, solutions miscible with oil, powders (DP), capsule suspensions (CS), seeddressing compositions, granules for broadcasting and soil application, spray granules, coating granules and absorbent 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 described in the following literature, for example, Winnacker-Küchler, “Chemische Techonologie” [Chemical Processes], Vol. 7, C. Hauser Verlag Munich, 4th ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, NY, 1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

[0120] Necessary formulation adjuvants, such as inert substances, surfactants, solvents, and other additives, are also known and described in the following documents, for example, Watkins's "Handbook of Powder Diluents, Insecticides, and Carriers," 2nd ed., Darland, Caldwell, NJ; Hv01phen's "Introduction to Clay Colloid Chemistry," 2nd ed., J. Wiley and Sons, NY; C. Marsden's "Solvent Guide," 2nd ed., Interscience, NY 1963; McCutcheon's "Annual Report on Detergents and Emulsifiers," MC Publishing, Ridgewood, NJ; Sisley and Wood, "Encyclopedia of Surfactants," Chemical Publishing, NY 1964; of [Ethylene oxide adduct surfactants], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Küchler's "Chemische Technologie" [Chemical Processes], Vol. 7, C. Hauser Verlag Munich, 4th edition 1986.

[0121] Wettable powders are uniformly dispersible in water and, in addition to the active ingredient, include diluents or inert substances, ionic and nonionic surfactants (wetting agents, dispersants), such as polyethoxyalkylphenols, polyethoxy fatty alcohols, polyoxyethyl aliphatic amines, fatty alcohol polyethylene glycol ether sulfates, alkyl sulfonates, alkyl phenyl sulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyl taurate. To prepare wettable powders, the active ingredient of the herbicide is finely ground, for example using common equipment such as hammer mills, fan mills, and jet mills, while adjuvants are mixed in simultaneously or sequentially.

[0122] Concentrated emulsions are prepared by dissolving active ingredients in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of higher-boiling aromatic compounds or hydrocarbons, and then adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used include, for example, calcium alkylaryl sulfonate of calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyethylene glycol esters, alkyl aromatic polyethylene glycol ethers, fatty alcohol polyethylene glycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters, or polyethylene oxide sorbitan esters such as polyethylene oxide sorbitan fatty acid esters.

[0123] The active substance and finely ground solid material are ground to obtain a powder. The solid material may be talc, natural clay such as kaolin, bentonite, and pyrophyllite, or diatomaceous earth. A water- or oil-based suspension may be prepared, for example, by wet grinding using a commercially available glass bead mill, with or without the addition of a surfactant of the other formulation type mentioned above.

[0124] Emulsions, such as oil-in-water (EW) emulsions, can be prepared using an aqueous organic solvent, a stirrer, a colloid mill, and / or a static mixer, and if necessary, by adding a surfactant of another formulation type as described above.

[0125] Granules can be prepared by spraying the active material onto an adsorbent and granulating it using an inert material, or by concentrating the active material onto the surface of a carrier such as sand or kaolinite and granulating it using a binder such as polyvinyl alcohol, sodium polyacrylate, or mineral oil. Suitable active materials can be granulated using methods for preparing fertilizer granules, and fertilizers can be mixed in if necessary. 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 without solid inert material.

[0126] For methods of preparing granules using grinding discs, fluidized beds, extruders, and spraying, see the following processes, for example, “Spray Drying Handbook,” 3rd edition, 1979, G. Goodwin Ltd., London; J.E. Browning, “Agglomeration,” Chemicals and Engineering, 1967, 147ff; and “Perry’s Chemical Engineer’s Handbook,” 5th edition, McGraw-Hill, New York, 1973, 8–57. For information on formulations of crop protection products, see, for example, G.K. C. Lingman, “Weed Control as a Science,” John Wiley and Sons, New York, 1961, 81–96; and JD. F. Greyer, SAEvans, “Weed Control Handbook,” 5th edition, Blackwell Scientific Rublications, Oxford University Press, 1968, 101–103.

[0127] Agricultural chemical formulations typically contain 0.1% to 99%, particularly 0.1% to 95%, of active ingredients of formulas I and I' by weight. The concentration of active ingredients in wettable powders is, for example, from about 10% to 99% by weight, with the usual formulation components constituting the remainder to 100% by weight. The concentration of active ingredients in concentrated emulsions can be from about 1% to 90% by weight, preferably 5% to 80%. Powder formulations contain 1% to 30% by weight of active ingredients, typically preferably 5% to 20% by weight; however, sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight. The content of active ingredients in aqueous suspension granules depends primarily on whether the active ingredient is liquid or solid, and on the adjuvants, fillers, etc., used during granulation. The content of active ingredients in aqueous suspension granules is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

[0128] The formulation of the active substance may also include thickeners, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, defoamers, evaporation inhibitors, and pH and viscosity adjusters that are commonly used in all cases.

[0129] Based on these formulations, they may also be mixed with other insecticidal active substances such as insecticides, acaricides, herbicides and fungicides, or with safeners, fertilizers and / or plant growth regulators. The mixing method may be pre-mixed or bottled.

[0130] Suitable active substances that can be mixed with the active substances of the present invention in compound formulations or tank-mixed formulations include, for example, known substances in the "World Encyclopedia of New Pesticide Varieties Technology", China Agricultural Science and Technology Press, 2010.9 and the literature cited herein. For example, the following herbicidal active substances can be mixed with mixtures of Formula I and Formula I' (Note: the name of the compound, either the common name according to the International Organization for Standardization (ISO) or the chemical name, with a code where appropriate): acetochlor, butachlor, metolachlor, isopropachlor, isopropachlor, succinate, chlorpyrifos, chlorpyrifos, naphthylpropachlor, R-L-naphthylpropachlor, propargite, benzylthiamethoxam, bisbenzylthiamethoxam, pyrifluquinazon, chlorpyrifos, flubutyroxyfen, brobutyroxyfen, dimethomorph, high-efficiency dimethomorph, ethoxybenzyl, flubutyroxyfen, methoxyfenazon, pyrifluquinazon, isoxaflutole, high-efficiency methyl methoxyfenozide, high-efficiency wheatgrass. Propranolol, Acetylchlor, Clethodim, Butyroxychlor, Cyprochlor, Flusulfanilamide, Heptylchlor, Isobutanil, Propylenechlor, Terbutaline, Metolachlor, Metolachlor, Loquat, Trimethylphenoxychlor, Chlorpyrifos, Propylenechlor, Pendimethalin, Carbohydrate, New Yanling, Tricyclic Succinylchlor, Butylchlor, Forsythiachlor, Benzosulfuron, Quinopyr, Benflufenican, Naphthylpropane, Acetylmetholachlor, Naphthylchlor, Thiamethoxam, Pyrazosulfuron, Benzodazole, Clethodim, Butamidine, Flupyrazole, Atrazine, Simazine, Prochloraz, Cypermethrin, Ciprofloxacin, Atrazine, Prochlorazine, Isopropanil, Fluroxypyrin, Terbutaline, Terbutaline, Triazine Fluroxypyrin, Cyprochlor, Ganpozine Herbicides, chlorpyrifos, simazine, azidophos, diquat, isoamyl acetate, cyprodinil, atrazine, terbufos, methoxypropazine, cyanazine, cyazofamid, clodinil, atrazine, cypermethrin, glycyrrhizin, cyanuric acid, Indaziflam, chlorsulfuron, mesosulfuron, bensulfuron, chlorpyrifos, bensulfuron, thiasulfuron, pyrimisulfuron, mesosulfuron-methyl, sodium iodosulfuron, formamidosulfuron, ethersulfuron, etherbensulfuron, mesosulfuron, nicosulfuron, aminebensulfuron, acylsulfuron, ethoxysulfuron, cyprosulfuron, sulfadiazine, tetrazoliumsulfuron, pyrimisulfuron, monosulfuron, monosulfuron, fluazolidone, flupyrimisulfuron, flupyrimisulfuron , including: epoximsulfuron, pyrazosulfuron, flupyrimisulfuron, propanilsulfuron, trifluprosulfuron, sulfonylsulfuron, trifluralinsulfuron, flusulfanilamide, trifluralin, sodium mesosulfuron, flupyrimisulfuron, thiosulfuron, pyrimisulfuron, propyrisulfuron, pyrazosulfuron, trifluralin, flusulfanilamide, quizalofop-p-ethyl, ethoxyflufenoxam, oxyflufenoxam, methylflufenoxam, methoxyflufenoxam, trifluralin, fluorinated oxychloride, flufenoxam, oxychloride, metolachlor, methylflufenoxam, halosafen, chlormequat chloride, isoproturon, linuron.Diuron, Saprolegnia, Fluroxypyr, Benzothiazoline, Methionylbenzyl, Benzothiazoline, Sulfothiazoline, Isoxadixyl, Terbuthiazoline, Clotrazoxadixyl, Chlorobromonium, Methylsulfuron, Acetazol, Methoxysulfuron, Bromosulfuron, Methoxysulfuron, Chlorfluazol, Benzouron, Cyclosulfuron, Fenitrothion, Flusulfuron, Rumab, Fipronil, Rumab, Isofenbamectin, Cyclosulfuron, Thifluzuron, Butyrazosulfuron, Fipronil, Methionyl, Trimethomorph, Oxazol, Monisouron, Anisuron, Methiuron, Chloreturon, Tetraflurium, Betaine, Betaine-ethyl, Betaine, Sulfochlor, Terbuchlor, Oxalide, Aniline, Chlorfenapyr, Dichlorfenapyr, Benzophenate, Chlorpyrifos, Carbo xazole, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbasulam, Butyrazosulfan, Herbadum, Metrazosulfan, Herbadum, Wild Grass, Herbadum, Herbadum, Herbadum, Herbadum, Herbadum, Herbadum, Herbadum, Herbadum, Herbadum, Herbadum, Isopolinate, Methiobencarb, 2,4-D Butyl Acetate, 2,4-D Sodium Chloride, 2,4-D Isooctyl Acetate, 2,4-D Sodium Salt, 2,4-D Dimethylamine Salt, 2,4-D Chlorethyl Thiate, 2,4-D Chlorine, 2,4-D Propionic Acid, High 2,4-D Propionate, 2,4-D Butyric Acid, 2,4-D Chlorpropionic Acid, 2,4-D Chlorine Propionate, 2,4,5-chlorobutyric acid, 2,4,5-propylpropionic acid, 2,4,5-propylbutyric acid, 2,4,5-chloroamine salt, dicamba, quizalofop-p-ethyl, cyhalofop-p-ethyl, methoxytrichlorobenzoic acid, quizalofop-p-ethyl, quizalofop-p-ethyl, fluazinam, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, cyhalofop-p-ethyl, quizalofop-p-ethyl, cyhalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl Opalin, propargyl, glyphosate, barnyardphos, glufosinate, methyl parathion, glyphosate, piperazine, diammonium phosphate, dimethoate, phosmet, fenpropathrin, fenpropathrin, fenpropathrin, dimethoate, fenpropathrin, imazalil, imazalil ethionate, imazalil quinolinic acid, methoxymethylene, methoxymethylene ammonium salt, imazalil, imazalil, clopyralid, clopyralid isooctyl ester, dichloropyridine acid, aminopyridine acid, trichloropyridine acid, fluthion, haloxypyridine, trichloropyridine phenol, thiamethoxam, flupyridine, clopyralid, flupyridine, trichloropyridine butoxyethyl ester, cliodinate, clethodim, thiamethoxam, quizalofop-p-ethyl, cyclobenzyl, butenazol, oxadiazon, pyranazol, buthidazoleAmetridione, Amibuzin, bromobenzonitrile, octanoyl bromobenzonitrile, octanoyl iodobenzonitrile, iodobenzonitrile, diphenylacetonitrile, bispyribac-sodium, hydroxydimethalin, Iodobonil, pyrimethanil, diflubenzuron, penoxsulam, sulfadiazine, chlorpyrifos-sulfuron-methyl, dichlorvos-sulfuron-methyl, flumethrin, bispyribac-sodium, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, bispyribac-sulfuron-methyl, nicosulfuron-methyl, sulfadiazine, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, isoxazin, isoxazin, Fenoxasulfon e. Methiozolin, isopyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, benzylazine, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flumetsulam, pyrazosulfuron, pyrazosulfuron, flumetsulam, mesotrione, fluroxypyr, pyrazosulfuron, flupropacil, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flupropacil, pyrazosulfuron, flupropacil, pyrazosulfuron, flupropacil, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pentachlorophenol (sodium), pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, dinitrophenol, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron Oxadiazon, Flupyrazosulfuron, Metazon, Tetracycline, Flupyrazosulfuron, Herbicides, Bromhexidine, Dimethoate, Pyridafol, Oxadiazon, Oxadiazon, Pyridafol, Pyridafol, Quinclorac, Quinclorac, Bendasone, Pyridafol, Oxadiazon, Oxadiazon, Isoxadiazon, Cyclohexafen, Isopropyltriazon, Propyltriazon, Indoxadixyl, Chlorine Sodium, cogon grass ash, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, forage grass, bromophenol oxime, triazole sulfonate, methomyl, furazolidone, furazolidone, ethoxysulfuron, pyrimethanil, chlorphthalic acid, flurfluthrin, barnyardgrass, acrolein, bensulfuron-methyl, metribuzin, oat ester, thiamethoxam, styracil, hydroxyzine, methoxybenzone, pyrimethanil, chlorpyrifos, trichloropropionic acid, A lorac, Diethamquat, Etnipromid, Iprymidam, Ipfencarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapin, methylsulfuron, Cambendichlor, Cypropyridine acid, Thiamethoxam, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, pyrazole cypermethrin, furazolidone, oxadiazon, bis(oxazolyl)acrylic acid, dichloropropenylamine, fluorochloropyridinium, DOW fluorochloropyridinium, UBH-509.D489,LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO535, D K-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023. ,

[0131] When used, commercially available formulations are diluted in a common manner if necessary, such as with water for wettable powders, concentrated emulsions, suspensions, and granules suspended in water. Powders, granules for soil application, or solutions for broadcasting and spraying generally do not require further dilution with an inert substance before use. The required dosage of compounds of formula I and I' varies with external conditions, such as temperature, humidity, and the nature of the herbicide used. It can vary considerably, for example, from 0.001 to 1.0 kg ai / ha, or more active material, but is preferably between 0.005 and 750 g ai / ha, particularly between 0.005 and 250 g ai / ha. Detailed Implementation

[0132] The following examples are for illustrative purposes only and should not be construed as limiting the invention in any way. The scope of protection of this invention is defined by the claims.

[0133] Given the economic efficiency and diversity of the compounds, we preferentially synthesized a number of compounds, some of which are listed in Table 1 below. The specific compound structures and corresponding compound information are shown in Table 1. The compounds in Table 1 are only for better illustration of the present invention and do not limit the invention. Those skilled in the art should not interpret this as limiting the scope of the above-mentioned subject matter of the invention to the following compounds.

[0134] Table 1. Compound structures and their properties 1 HNMR

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156] Table A has the same structure as Table 1 above, except that it will have a chiral center ( The racemic compounds (i.e., compounds 1-50, 52-90, 92-93, 95-152, 154-192, 194-195 and 197-236) with the carbon atom (C*) bonded to X3 and X4 being the chiral center (i.e., when X3 and X4 are not the same) are replaced with the corresponding S configurations and the compounds without chiral centers at the corresponding positions are deleted. In Table A, the entries under the "Serial Number" column are described as "1(S)-50(S), 52(S)-90(S), 92(S)-93(S), 95(S)-152(S), 154(S)-192(S), 194(S)-195(S) and 197(S)-236(S)". For example, “1(S)” corresponds to the S configuration of compound “1” in Table 1, and “119(S)” corresponds to the S configuration of compound “119” in Table 1.

[0157] Table B shows the structures of the compounds and their... 1 H NMR data

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The raw materials can be commercially available or prepared by methods known in the literature or as detailed in the description. Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention. Although specific raw materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar raw materials and conditions. Such variations or modifications to the preparation methods of the present invention, such as various isomers of the compounds, are all included within the scope of the present invention. Furthermore, the preparation methods described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protecting appropriate groups during the reaction process, etc.

[0170] The following method examples are provided to further illustrate the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further explain the invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds shown in the table below are either commercially available or can be easily prepared by those skilled in the art.

[0171] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0172] 1. Synthesis of Compound 55

[0173] (1) 55-1 (1.18 g, 1.0 eq., 10 mmol) was dissolved in THF (30 mL), and NaH (500 mg, 1.25 eq., 12.5 mmol, 60% purity) was added under an ice-water bath. After stirring for 30 minutes under an ice-water bath, 55-2 (1.93 g, 1.0 eq., 10 mmol) was added, and the mixture was slowly brought to room temperature and stirred at room temperature for 12 h. The reaction was monitored by TLC until complete. After the reaction was complete, the reaction solution was slowly added to water (200 mL) to quench the reaction. The mixture was extracted three times with ethyl acetate (20 mL), and the organic phases were combined and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated to obtain crude compound 55-3 (1.88 g, 82% yield, 8.2 mmol, yellow oily liquid), which was directly added to the next step.

[0174]

[0175] (2) Add a (20 g, 91.5 mmol, 1.0 eq) to 150 mL of DMF, then slowly add NCS (13.4 g, 100.7 mmol, 1.1 eq) to the reaction solution at 35 °C. After the addition is complete, stir the reaction solution at 35 °C for 1.5 hours. LCMS analysis shows that the starting materials have basically reacted completely. Pour the reaction solution into 100 mL of HCl (1 M) and extract with dichloromethane. Wash the organic phase with saturated brine (100 mL * 3). After concentrating the organic phase, crude product 55-4 (26 g, crude product) (yellow oil) is obtained. The crude product is directly added to the next step.

[0176]

[0177] (3) 55-4 (1.6 g, 6.7 mmol, 1.0 eq) and Et3N (1.01 g, 10.05 mmol, 1.5 eq) were added to 20 mL of DCM. Then, 55-3 (1.84 g, 8 mmol, 1.2 eq) was added to the reaction solution at 0 °C. After reacting at 0 °C for 1 hour, the product was detected by LCMS. 100 mL of water was added to the reaction solution, and the mixture was extracted with dichloromethane (100 mL * 3). The organic phase was dried over anhydrous sodium sulfate, concentrated, and the crude product was purified by column chromatography to obtain 55-5 (1.94 g, 65% yield, 4.35 mmol, yellow solid).

[0178]

[0179] (4) 55-5 (1.80 g, 4.0 mmol, 1.0 eq), Fe powder (672 mg, 12.0 mmol, 3 eq), NH4Cl (530 mg, 10.0 mmol, 2.0 eq), and water (5 mL) were added sequentially to 20 mL of EtOH. The reaction solution was then reacted at 80 °C for 2 hours. LC-MS analysis showed that the starting material disappeared, and the main peak was the product peak. The reaction solution was filtered through diatomaceous earth, concentrated to remove ethanol, and then water (100 mL) was added. After extraction with ethyl acetate, the solution was concentrated to obtain a black crude product. The crude product was purified by column chromatography to obtain 55-6 (1.41 g, 85% yield, 3.4 mmol, yellow solid).

[0180]

[0181] (5) 55-6 (1.2 g, 2.89 mmol, 1.0 eq) and 55-7 (0.50 g, 3.18 mmol, 1.1 eq) were added to 10 ml of toluene, and the reaction solution was heated at 110 °C for 1 hour. LCMS showed that the starting material had basically reacted completely, and the main peak was the product. After concentrating the solvent, the crude product was separated by column chromatography to obtain 55-8 (1.29 g, 83.4% yield, 2.41 mmol, yellow solid).

[0182]

[0183] (6) Add 55-9 (0.48 g, 2.1 mmol, 1.5 eq) and AcONa (58 mg, 0.7 mmol, 0.5 eq) to 10 ml of DMF. Then add 55-8 (0.75 g, 1.4 mmol, 1.0 eq) to the reaction solution at 60 °C and react at 60 °C for 1 hour. The product was detected by LCMS. After adding water (10 ml) to the reaction solution, extract with ethyl acetate. Wash the organic phase with saturated brine (20 ml * 1). After concentrating the organic phase, the crude product was separated by column chromatography to obtain 55 (0.58 g, 72% yield, 1.0 mmol, yellow solid).

[0184]

[0185] 2. Synthesis of Compound 119

[0186] (1) Diethyl oxalate (5.0 g, 34.2 mmol, 1.0 eq) was dissolved in anhydrous THF (80 mL). Under nitrogen protection, the mixture was cooled to -60 °C in a dry ice-ethanol bath. Cyclopropylmagnesium bromide (1 M in THF) (37.6 mL, 37.6 mmol, 1.1 eq) was slowly added dropwise to the system. The reaction was maintained at low temperature for 1 h. LCMS analysis showed that the starting material had almost disappeared and a new peak had formed. After the temperature was raised to room temperature, a saturated ammonium chloride aqueous solution was slowly added dropwise to quench the reaction. The mixture was diluted with 100 mL of water, and the aqueous phase was extracted with EA (3 x 100 mL). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent, yielding crude product 119-1 (4.9 g, quantitative).

[0187] The crude product can be used directly in the next reaction without purification.

[0188]

[0189] (2) Methyltriphenylphosphine bromide (12.2 g, 34.2 mmol, 1.0 eq) was dissolved in anhydrous THF (100 mL). Under nitrogen protection, the mixture was cooled to -60 °C in a dry ice-ethanol bath. LiHMDS (1 M in THF) (34.2 mL, 34.2 mmol, 1.0 eq) was slowly added to the system, and the reaction was maintained at low temperature for 1 h. Then, a tetrahydrofuran solution of the previous product 119-1 (4.9 g, 34.2 mmol, 1.0 eq) was slowly added to the system. After the addition was complete, the reaction was maintained at low temperature for 2 h. LCMS showed that the starting material disappeared and a new peak was formed. The mixture was then brought to room temperature, and a saturated ammonium chloride aqueous solution was slowly added dropwise to quench the reaction. The mixture was concentrated under reduced pressure to remove most of the solvent. The remaining portion was diluted with 100 mL of water, and the aqueous phase was extracted with diethyl ether (2 x 100 mL). The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent, yielding product 119-2 (3.2 g, crude product yield 67%). The crude product was used directly in the next reaction without purification.

[0190]

[0191] (3) Add starting material 55-4 (2.8 g, 11.4 mmol, 0.5 eq) and Et3N (1.7 g, 17.1 mmol, 1.5 eq) to 60 mL of DCM. Then, add product 119-2 (3.2 g, 22.8 mmol, 1.0 eq) from the previous step to the reaction solution at 0 °C. After reacting at 0 °C for 1 hour, the product was detected by LCMS. Add 50 mL of water to the reaction solution, extract with dichloromethane (50 mL * 3), dry the organic phase with anhydrous sodium sulfate, concentrate, and purify the crude product by column chromatography to obtain product 119-3 (320 mg g, 8% yield) (yellow oil).

[0192]

[0193] (4) In 20 mL of EtOH, the product 119-3 (320 mg, 0.9 mmol, 1.0 eq), Fe powder (151 mg, 2.7 mmol, 3 eq), NH4Cl (95 mg, 1.8 mmol, 2 eq), and water (5 mL) were added sequentially. The reaction solution was then reacted at 80 °C for 0.5 hours. LC-MS analysis showed that the starting material disappeared, and the main peak was the product peak. The reaction solution was filtered through diatomaceous earth, concentrated to remove ethanol, and then water (100 mL) was added. After extraction with ethyl acetate, the solution was concentrated to obtain a black crude product. The crude product was purified by column chromatography to obtain product 119-4 (190 mg, 65% yield) (yellow oil).

[0194]

[0195] (5) Add product 119-4 (190 mg, 0.6 mmol, 1.0 eq) from the previous step, 10 mL of acetic acid, and starting material 119-5 (125 mg, 0.6 mmol, 1.0 eq) to a 50 mL round-mouth flask. Heat to 125 °C and react for 20 min. LC-MS detection showed product formation. Cool to room temperature, concentrate under reduced pressure to remove acetic acid, add silica gel for column purification, and concentrate to obtain product 119-6 (160 mg, 56% yield) (pale yellow oil).

[0196]

[0197] (6) Add the product 119-6 (160 mg, 0.33 mmol, 1.0 eq), potassium carbonate (228 mg, 1.65 mmol, 5.0 eq), and methyl iodide (140 mg, 0.99 mmol, 3.0 eq) from the previous step to 10 mL of anhydrous DMF, and react at room temperature for 3 h. LCMS showed that the starting material disappeared and the product was formed. Dilute with EA (60 mL), wash the organic phase with water (2 x 30 mL), wash with 30 mL of saturated brine, dry with anhydrous sodium sulfate, filter and concentrate, and purify the crude product by column chromatography to obtain product 119 (100 mg, 60% yield) (yellow oil).

[0198]

[0199] (7) Compound 119 was separated by chiral HPLC (column type: AD-5H 5μm 21.2x250mm, mobile phase: n-hexane:ethanol = 7:3, flow rate: 20ml / min, wavelength: 220nm) to obtain 119(S) (LC purity: 98%, 93% ee).

[0200]

[0201] 3. Synthesis of Compound 206

[0202] (1) Compound 206-1 was prepared according to the method described above for compound 119-4. Then, 206-1 (0.6 g, 2.0 mmol, 1.0 eq) and 206-2 (0.38 g, 2.2 mmol, 1.1 eq) were added to 10 mL of 1,4-dioxane. The reaction solution was heated at 110 °C for 1 hour. LCMS showed that the reactants had basically reacted completely, and the main peak was the product. After concentrating the solvent, the crude product was separated by column chromatography to obtain 206-3 (0.7 g, 83.4% yield) (white solid).

[0203]

[0204] (2) 206-4 (0.47 g, 2.1 mmol, 1.5 eq) and AcONa (58 mg, 0.7 mmol, 0.5 eq) were added to 10 ml of DMF. Then, 206-3 (0.6 g, 1.4 mmol, 1.0 eq) was added to the reaction solution at 60 °C, and the reaction was carried out at 60 °C for 1 hour. The product was detected by LCMS. Water (10 ml) was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine (20 ml * 1). After concentrating the organic phase, the crude product was separated by column chromatography to obtain 206 (0.4 g, 61.4% yield) (white solid).

[0205]

[0206] 4. Synthesis of Compound 229

[0207] (1) Add 55-4 (2g, 7.94mmol, 1.0eq) and Et3N (1.2g, 11.88mmol, 1.5eq) to 200ml of DCM, then add 229-1 (1.02g, 7.97mmol, 1.0eq) to the reaction solution at 0℃. Slowly raise the temperature to 20℃ and react for 2-4 hours. LCMS detects the product. Add 100ml of water to the reaction solution, extract with dichloromethane (50ml*3), dry the organic phase with anhydrous sodium sulfate, concentrate, and purify the crude product by column chromatography to obtain 229-2 (860mg, 32% yield).

[0208]

[0209] (2) 229-2 (860 mg, 2.5 mmol, 1.0 eq), Fe powder (420 mg, 7.5 mmol, 3.0 eq), NH4Cl (265 mg, 5.0 mmol, 2 eq), and water (12.5 ml) were added sequentially to 50 ml of EtOH. The reaction solution was then reacted at 80 °C for 2 hours. LC-MS analysis showed the disappearance of the starting material and the presence of the product as the main peak. After cooling, the reaction solution was filtered through diatomaceous earth, concentrated to remove ethanol, and then water was added. After extraction with ethyl acetate, the solution was concentrated to obtain a black crude product, 229-3. The crude product was directly used in the next step (720 mg, 90% yield).

[0210]

[0211] (3) 229-3 (450 mg, 1.43 mmol, 1.0 eq), DMAP (17 mg, 0.14 mmol, 0.01 eq), triethylamine (217 mg, 2.15 mmol, 1.5 eq), and thiocarbonyl diimidazole CDI-S (306 mg, 1.72 mmol, 1.2 eq) were added to 20 mL of toluene. The reaction mixture was reacted at room temperature for 1 hour. After removing the toluene by rotation, water was added, and the mixture was extracted with ethyl acetate. The organic phase was stirred and passed through a column. The crude product was purified by column chromatography to obtain 229-4 (270 mg, 53% yield).

[0212]

[0213] (4) Add 229-4 (270 mg, 0.76 mmol, 1.0 eq), cesium carbonate (739 mg, 2.27 mmol, 3.0 eq), and 229-5 (153 mg, 0.84 mmol, 1.1 eq) to 10 ml of DMF. After stirring the reaction solution at 0 °C for 2-3 h, the starting material disappeared and the main peak was the product, as detected by LCMS. Add water to the reaction solution, extract with ethyl acetate, wash with saturated brine, mix the organic phase and pass through a column. The crude product was purified by column chromatography to obtain 229-6 (102 mg, 27% yield).

[0214]

[0215] (5) Add 229-6 (102 mg, 0.21 mmol, 1.0 eq), iodomethane (118 mg, 0.83 mmol, 4.0 eq), and potassium carbonate (57 mg, 0.41 mmol, 2.0 eq) sequentially to 10 mL of DMF. Incubate the reaction mixture at 25-30 °C for 4-6 hours, or until complete as determined by LC-MS. After adding water, extract with ethyl acetate, wash with saturated brine, mix the organic phase, and pass through a column. Purify the crude product by column chromatography to obtain 229 (70 mg, 67% yield).

[0216]

[0217] 5. Synthesis of compounds 1-62

[0218] 1) Compound 1-62-1 was prepared according to the synthetic method described in 229-3 above. Then, 1-62-1 (0.6 g, 2.0 mmol, 1.0 eq) and phenyl chloroformate (0.34 g, 2.2 mmol, 1.1 eq) were added to 10 ml of toluene. The reaction solution was heated at 110 °C for 1 hour. LCMS showed that the reactants had basically reacted completely, and the main peak was the product. After concentrating the solvent, the crude product was separated by column chromatography to obtain 1-62-2 (0.7 g, 83.4% yield) (white solid).

[0219]

[0220] 2) 206-4 (0.48 g, 2.1 mmol, 1.5 eq) and AcONa (58 mg, 0.7 mmol, 0.5 eq) were added to 10 mL of DMF. Then, 1-62-2 (0.6 g, 1.4 mmol, 1.0 eq) was added to the reaction solution at 60 °C, and the reaction was continued at 60 °C for 1 hour. The product was detected by LCMS. Water (10 mL) was added to the reaction solution, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine (20 mL x 1). After concentrating the organic phase, the crude product was separated by column chromatography to obtain the 1-62-racemic mixture (0.4 g, 61.4% yield) (white solid).

[0221]

[0222] 3) The racemic mixture of compound 1-62 (0.5 g, 98% purity) was analyzed by chiral HPLC (Column: AD-5H; Column Size: 3 cm x 25 cm, 5 μm; Injection: 2.0 mL; Mobile phase: Hex:i-PrOH (20% EtOH) = 6:4; Flow rate: 20 mL / min; Wavelength: UV 254 nm; Temperature: 25 nm). O C; Sample solution: 50 mg / 2 ml in EtOH; Run time = 60 mins) After separation and concentration, white solids 1-62 (0.16 g, Rt = 10.51 min, 100% ee) and 1-62-R configuration (0.13 g, Rt = 30.81 min, 99.8% ee) were obtained.

[0223]

[0224] Bioactivity evaluation:

[0225] The activity level standards for plant damage (i.e., growth control rate) are as follows:

[0226] Level 5: Growth control rate is above 85%;

[0227] Level 4: Growth control rate is greater than or equal to 60% and less than 85%;

[0228] Level 3: Growth control rate greater than or equal to 40% and less than 60%;

[0229] Level 2: Growth control rate greater than or equal to 20% and less than 40%;

[0230] Level 1: Growth control rate greater than or equal to 5% and less than 20%;

[0231] Grade 0: Growth control rate is less than 5%.

[0232] The above growth control rates are fresh weight control rates.

[0233] Post-emergence testing experiment:

[0234] Seeds of monocotyledonous and dicotyledonous weeds (such as shepherd's purse, shepherd's purse, velvetleaf, cleavers, chickweed, wild oats, watercress, Japanese wild oats, goosegrass, purslane, hard grass, fleabane, candle grass, speedwell, wild oats, jointed goatgrass, purslane, amaranth, lambsquarters, dayflower, sow thistle, field bindweed, sow thistle, black nightshade, iron amaranth, crabgrass, barnyard grass, green foxtail grass, golden foxtail grass, goosegrass, duckweed, arrowhead, firefly sedge, nutgrass, sedge, purslane, purslane, cocklebur, morning glory, white wine grass, etc.) and the main Crop seeds (wheat, corn, rice, soybean, cotton, rapeseed, millet, sorghum, potato, sesame, castor bean, etc.) were placed in plastic basins filled with soil, then covered with 0.5-2 cm of soil. The plants were then allowed to grow in a suitable greenhouse environment. Two weeks after sowing, test plants were treated at the 2-3 leaf stage. The compound of this invention was dissolved in acetone, then Tween 80 was added, and methyl oleate emulsifiable concentrate at 1.5 L / ha was used as a synergist. The solution was diluted with water to a specific concentration and sprayed onto the plants using a spray tower. After three weeks of cultivation in a greenhouse, the weed control effect was statistically analyzed. The compound dosages used were 500, 250, 125, 60, 15, and 7.5 g ai / ha, with three replicates, and the average value was taken. Representative data are listed in Table 2-6.

[0235] Table 2 Results of post-emergence weed control experiment

[0236]

[0237]

[0238] Table 3 Results of the post-emergence weed control experiment

[0239]

[0240]

[0241] Table 4 Results of Post-emergence Weed Trial

[0242] 105 5 5 5 5 125 105(S) 5 5 5 5 125 119 5 5 5 5 125 119(S) 5 5 5 5 125 126 5 5 5 5 125 129 5 5 5 5 125 132 5 5 5 5 125 134 5 5 5 5 125 135 5 5 5 5 125 136 5 5 5 5 125 142 5 5 5 5 125 152 5 5 5 5 125 218 5 5 5 5 125 219 5 5 5 5 125 220 5 5 5 5 125 226 5 5 5 5 125 228 5 5 5 5 125 228(S) 5 5 5 5 125 229 5 5 5 5 125 230 5 5 5 5 125 231 5 5 5 5 125

[0243] Table 5 Results of the post-emergence weed control experiment

[0244]

[0245]

[0246] Table 6 Results of the post-emergence weed control experiment

[0247]

[0248]

[0249] Note: N represents no data; control compound A: Reference compound B:

[0250] Pre-seeding test experiment:

[0251] Seeds of monocotyledonous and dicotyledonous weeds, as well as seeds of major crops (wheat, corn, rice, soybean, cotton, rapeseed, millet, and sorghum), were placed in plastic basins filled with soil and covered with 0.5-2 cm of soil. The tested compounds of this invention were dissolved in acetone, then Tween 80 was added, and the solution was diluted with water to a specific concentration. The solutions were sprayed immediately after sowing. After 4 weeks of cultivation in a greenhouse following application, the experimental results were observed. It was found that most of the herbicides of this invention showed excellent efficacy at a dosage of 250 g ai / ha, especially against barnyard grass, crabgrass, and velvetleaf, and many compounds exhibited good selectivity for corn, wheat, rice, and soybeans.

[0252] Meanwhile, through testing on major weeds in wheat and rice fields, we found that the compounds described in this invention generally have good weed control efficacy. In particular, we noted that they have extremely high activity against broadleaf weeds and sedges resistant to ALS inhibitors, such as arrowhead, fireweed, sedge, shepherd's purse, shepherd's purse, cleavers, nutgrass, and nutgrass, and have very good commercial value.

[0253] Safety evaluation of transplanted rice and weed control efficacy evaluation in paddy fields:

[0254] After filling 1 / 1,000,000-hectare tanks with paddy field soil, sow seeds of barnyard grass, rush, and wolfsbane, and gently cover them with soil. Then, place the tanks in a greenhouse with water at a depth of 0.5-1 cm. The tubers of arrowhead are then planted the next day or two later. The water depth is maintained at 3-4 cm. When the barnyard grass, rush, and wolfsbane reach the 0.5-leaf stage, and the arrowhead reaches the initial leaf stage, a water-diluted solution of the wettable powder or suspension of the compound of this invention, prepared according to conventional formulation methods, is evenly dripped using a pipette to achieve the specified effective ingredient concentration.

[0255] In addition, after filling the 1 / 1,000,000-hectare tank with paddy field soil, the soil is leveled to a water depth of 3-4 cm. The next day, 3-leaf stage rice (japonica rice) is transplanted at a transplanting depth of 3 cm. The compound of the present invention is treated in the same way as described above on the 5th day after transplanting.

[0256] The growth status of barnyard grass, fireweed, wolfberry, and arrowhead was observed with the naked eye on day 14 after treatment, and the growth status of rice was observed on day 21 after treatment. The effects were evaluated according to the above-mentioned activity standard level. Many compounds showed excellent activity and selectivity.

[0257] Note: The seeds of barnyard grass, fireweed, and wolfsbane were all collected from Heilongjiang, China, and tests showed that they were resistant to conventional doses of pyrimisulfuron.

[0258] Furthermore, numerous tests have revealed that the compounds and their compositions described in this invention exhibit excellent selectivity against many grassy lawns, including Zoysia japonica, Bermuda grass, tall fescue, Kentucky bluegrass, ryegrass, and seashore paspalum, effectively controlling many key grassy weeds as well as broadleaf weeds. Tests on sugarcane, soybeans, cotton, sunflowers, potatoes, fruit trees, and vegetables under different application methods also demonstrated excellent selectivity and commercial value.

Claims

1. An aromatic compound containing a substituted isoxazoline, selected from any one of the following compounds: ， 。 2. An aromatic compound containing a substituted isoxazoline according to claim 1, characterized in that: In the compound, the carbon atoms bonded to X3 and X4 are both chiral centers and have an S configuration.

3. An aromatic compound containing a substituted isoxazoline, selected from any one of the following S-configuration compounds: ， 。 4. A herbicidal composition, characterized by comprising: It includes at least one of the aromatic compounds containing substituted isoxazoline as described in any one of claims 1-3, which has an effective herbicidal amount.

5. The composition of claim 4, wherein, It also includes pharmaceutical additives.

6. A method of controlling weeds, characterized by, This includes applying an effective amount of at least one of the aromatic compounds containing substituted isoxazoline as described in any one of claims 1-3, or the herbicide composition as described in claim 4 or 5, to plants or weedy areas.

7. Use of at least one of the aromatic compounds containing substituted isoxazoline as described in any one of claims 1-3, or the herbicide composition as described in claim 4 or 5, in the control of weeds.

8. The use according to claim 7, characterized in that, The aromatic compounds containing substituted isoxazoline are used to control weeds in useful crops, wherein the useful crops are genetically modified crops or crops treated with genome editing technology.

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