Quinazolinone compound, preparation method therefor, herbicidal composition thereof, and use thereof

Abstract

The present invention belongs to the technical field of agrochemicals, and particularly relates to a quinazolinone compound or a salt thereof, a preparation method therefor, a herbicidal composition thereof, and use thereof. The compound is represented by general formula I: wherein Q represents heterocyclyl, and R1, R2, R4, and R6 each independently represent hydrogen, halogen, cyano, nitro, alkyl, or the like; R3 represents an alkyl group that is unsubstituted or is substituted with at least one group selected from cyano, nitro, halogen, -OR21, -SR21, -(SO)R21, or -(SO2)R21; R5 and R7 each independently represent alkyl, alkenyl, alkynyl, or the like; X1, X2, X3, X4, X5, and X6 each independently represent hydrogen, halogen, alkyl, or the like. The compound has excellent herbicidal activity, is safe for crops, and has high selectivity.

Description

Quinazolinone compounds, their preparation methods, herbicidal compositions and applications Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a quinazolinone compound, its preparation method, herbicidal composition, and application. Background Technology

[0002] Weed control is a crucial aspect of achieving efficient agriculture. Although a wide variety of herbicides are available on the market, the weed-control 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

[0003] This invention provides a quinazolinone compound, its preparation method, herbicidal composition, and application. The compound exhibits excellent herbicidal activity, is safe for crops, and has high selectivity.

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

[0005] A quinazolinone compound or a salt thereof, as shown in general formula I:

[0006] Where Q represents a heterocyclic group,

[0007] R1, R2, R4, and R6 independently represent hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, and -OR, respectively. 21 -(CO)OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 ;

[0008] R3 represents unsubstituted or selected from cyano, nitro, halogen, -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 An alkyl group substituted with at least one group;

[0009] R5 and R7 independently represent alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclic, or are selected from cyano, nitro, halogen, cycloalkyl, aryl, heterocyclic, -(CO)OR 21 -OR21 -SR 21 -(SO)R 21 or -(SO2)R 21 An alkyl, alkenyl, or ynyl group substituted with at least one group;

[0010] X1, X2, X3, X4, X5, and X6 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, or cycloalkylalkyl, or two substituents on the same carbon atom connected to form unsubstituted or halogen-substituted -(CH2)2-, -(CH2)3-, -(CH2)4-, or -(CH2)5-, or two substituents on different carbon atoms connected to form -O-, or unsubstituted or halogen-substituted -CH2-, -(CH2)2-, -(CH2)3-, or -(CH2)4-;

[0011] R 21 Each of these can independently represent hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclic or heterocyclic alkyl.

[0012] The aforementioned cycloalkyl, cycloalkenyl, heterocyclic, or aryl groups are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 The aryl group is substituted by at least one group in 2, or the two adjacent carbon atoms on the aryl group are connected to an unsubstituted or halogen-substituted -O-CH2-O- to form a fused ring;

[0013] R 10 Each can independently represent hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, or haloalkynyl.

[0014] In one specific embodiment, R1, R2, R4, and R6 independently represent hydrogen, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, aryl, heterocyclic, and -OR, respectively. 21 -(CO)OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 ;

[0015] R3 represents unsubstituted or selected from cyano, nitro, halogen, -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 C1-C8 alkyl groups substituted with at least one group;

[0016] R5 and R7 independently represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, aryl, heterocyclic, or groups selected from cyano, nitro, halogen, C3-C8 cycloalkyl, aryl, heterocyclic, and -(CO)OR. 21 -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl groups substituted with at least one group;

[0017] X1, X2, X3, X4, X5, and X6 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkyl-C1-C8 alkyl, or two substituents on the same carbon atom connected to form unsubstituted or halogen-substituted -(CH2)2-, -(CH2)3-, -(CH2)4- or -(CH2)5-, or two substituents on different carbon atoms connected to form -O-, or unsubstituted or halogen-substituted -CH2-, -(CH2)2-, -(CH2)3- or -(CH2)4-;

[0018] R 21 Each of these can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl-C1-C8 alkyl, aryl, aryl-C1-C8 alkyl, heterocyclic or heterocyclic-C1-C8 alkyl;

[0019] The aforementioned C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic, or aryl groups are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 ) 20 At least one group in the aryl group is substituted, or two adjacent carbon atoms on the aryl group are connected to an unsubstituted or halogenated -O-CH2-O- to form a fused ring;

[0020] R 10 Each of these can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, or halo-C2-C8 alkynyl.

[0021] In another embodiment, R1, R2, R4, and R6 independently represent hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, aryl, heterocyclic, and -OR, respectively. 21 -(CO)OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 ;

[0022] R3 represents unsubstituted or selected from cyano, nitro, halogen, -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 C1-C6 alkyl groups substituted with at least one group;

[0023] R5 and R7 independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, aryl, heterocyclic, or groups selected from cyano, nitro, halogen, C3-C6 cycloalkyl, aryl, heterocyclic, and -(CO)OR. 21 -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl groups substituted with at least one group;

[0024] X1, X2, X3, X4, X5, and X6 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl-C1-C6 alkyl, or two substituents on the same carbon atom connected to form unsubstituted or halogenated -(CH2)2-, -(CH2)3-, -(CH2)4- or -(CH2)5-, or two substituents on different carbon atoms connected to form -O-, or unsubstituted or halogenated -CH2-, -(CH2)2-, -(CH2)3- or -(CH2)4-;

[0025] R 21 Each of these can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heterocyclic or heterocyclic-C1-C6 alkyl;

[0026] The aforementioned C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, or aryl groups are each independently unsubstituted or 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, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 ) 20 At least one group in the aryl group is substituted, or two adjacent carbon atoms on the aryl group are connected to an unsubstituted or halogenated -O-CH2-O- to form a fused ring;

[0027] R 10 Each of these can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, or halo-C2-C6 alkynyl.

[0028] In another implementation, Q represents a heterocyclic group or

[0029] In another embodiment, R1, R2, and R4 independently represent hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, and -OR, respectively. 21 -(CO)OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 .

[0030] In another embodiment, R5 represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, aryl, heterocyclic, or is selected from cyano, nitro, halogen, C3-C6 cycloalkyl, -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 The C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl group is substituted with at least one group.

[0031] 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, in the compound term "cycloalkylalkyl," 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, alkenyl groups are, 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, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl groups are, for example, ethynyl, propynyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds can be in any position in each unsaturated group. Cycloalkyl groups are carbocyclic saturated ring systems having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl groups are monocyclic alkenyl groups having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bonds can be in any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0032] 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. 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

[0033] The terms "optional" or "optionally" mean that the event or situation described below may or may not occur, and the description includes instances where said event or situation occurs and instances where said event or situation does not occur. For example, the term "optionally...substituted" means that the specified atom or group is unsubstituted or substituted by one or more substituents. If a group is substituted by a group, this should be understood to mean that the group is substituted by one or more groups, either the same or different, selected from those groups mentioned. Furthermore, the same or different substitution characters contained in the same or different substituents are chosen independently and may be the same 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.

[0034] 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.

[0035] The method for preparing the quinazolinone compound or its salt includes the following steps: using the compound The reaction proceeds as an intermediate, where L represents a leaving group (such as OH, halogen, p-nitrophenoxy, or cyano), and the substituents R1, R2, R3, R4, and R5 are defined as described above.

[0036] In one specific implementation, (1) when Q represents Compound IV-1 is prepared by a condensation reaction of the compound represented by general formula II and the compound represented by general formula III-1, and then compound I-1 is prepared by a rearrangement reaction. The reaction equation is as follows:

[0037] (2) When Q represents Compound I-2 is prepared by a condensation reaction of the compound represented by general formula II and the compound represented by general formula III-2, and the reaction equation is as follows:

[0038] (3) When Q represents Compound I-3 is prepared by a condensation reaction of the compound represented by general formula II and the compound represented by general formula III-3, and the reaction equation is as follows:

[0039] The definitions of Y1, Y2, Y3, Y4, Y5, Y6, R1, R2, R3, R4, R5, R6, and R7 are as described above.

[0040] In one specific embodiment, the condensation reactions in step 1, reaction (2), and (3) are all carried out in the presence of a solvent.

[0041] In one specific embodiment, the rearrangement reaction in step 2 is carried out in the presence of a catalyst (such as acetone cyanohydrin), a base, and a solvent.

[0042] In another specific embodiment, a condensing agent and / or base are added to the condensation reactions in step 1, reaction (2) and (3).

[0043] In another specific embodiment, the solvent is selected from at least one of aromatic hydrocarbons (such as benzene, chlorobenzene or toluene), N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dichloroethane, dimethyl sulfoxide, 1,4-dioxane, dichloromethane or ethyl acetate.

[0044] In another specific embodiment, the base is selected from at least one of inorganic or organic bases, such as NaH, KH, NaOH, KOH, K2CO3, Na2CO3, NaHCO3, Cs2CO3, KF, CsF, 1,8-diazabicyclo[5.4.0]undec-7-ene, pyrazole, triethylamine, N,N-diisopropylethylamine, pyridine, potassium trimethylsilanol, AcOK, AcONa, MeONa, EtONa, t-BuONa, or t-BuOK, etc.

[0045] In another specific embodiment, the condensing agent in step 1, reaction (2) and (3) is selected from at least one of benzotriazine-1-yl-oxytripyrrolidinephosphine hexafluorophosphate (Py-BOP), N,N'-carbonyldiimide (CDI), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI), 1-hydroxybenzotriazole (HOBT), 1,3-dicyclohexylcarbodiimide (DCC) or N,N,N',N'-tetramethyl-O-(7-azabenzotriazine-1-yl)hexafluorophosphate urea (HATU).

[0046] An intermediate, as shown in Formula II.

[0047] In addition, compounds represented by general formula I can also be prepared by the method shown in CN114573516A, etc.

[0048] A herbicide composition comprising at least one of the quinazolinone compounds or their salts in an herbicidal effective amount, preferably further comprising a formulation adjuvant.

[0049] A method for controlling weeds, comprising applying a herbicidally effective amount of at least one of the quinazolinone compounds or their salts, or the herbicide composition thereof, to plants or weedy areas.

[0050] The use of at least one of the quinazolinone compounds or their salts, or the herbicide composition, in controlling weeds, preferably, the use of the quinazolinone compounds or their salts in controlling weeds in useful crops, more preferably, the useful crops including transgenic crops or crops treated with genome editing technology.

[0051] For many economically important monocotyledonous and dicotyledonous pests, the compounds of 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*.

[0052] 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*.

[0053] 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.

[0054] 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.

[0055] The compounds of Formula I of the present invention, or salts thereof, are preferably used in the cultivation of economically important genetically modified crops and ornamental plants, such as cereals, including 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 as herbicides for the cultivation of useful plants that are resistant or have been genetically engineered to be resistant to the toxic effects of the herbicides.

[0056] 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-0221044 A, EP-0131624 A). Several methods have been described, for example:

[0057] - To improve starch synthesis in plants, genetic engineering is used to modify crop plants (e.g., WO 92 / 11376, WO 92 / 14827, WO 91 / 19806);

[0058] - Transgenic crop plants resistant to specific herbicides, such as glufosinate-methyl (e.g., EP-0242236 A, EP-0242246 A), glyphosate-based herbicides (WO 92 / 00377), or sulfonylurea herbicides (EP-0257993 A, US-5013659 A);

[0059] - For example, genetically modified cotton plants can produce Bt toxins, which can defend against certain pests (EP-0142924 A, EP-0193259 A).

[0060] - A genetically modified crop plant with improved fatty acid composition (WO91 / 13972).

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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).

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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 formula I. Compounds of formula 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.

[0069] 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, “Chemische Technologie” [Chemical Processes], Vol. 7, C. Hauser Verlag Munich, 4th edition 1986.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] 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; “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, 181–96; and JD. F. Greyer, SAEvans, “Weed Control Handbook,” 5th edition, Blackwell Scientific Rublications, Oxford University Press, 1968, 101–103.

[0076] Agricultural chemical formulations typically contain 0.1% to 99%, particularly 0.1% to 95%, of active ingredient Formula I by weight. The concentration of active ingredient 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 ingredient in concentrated emulsions can be from about 1% to 90% by weight, preferably 5% to 80%. Powder formulations contain 1% to 30% active ingredient by weight, 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 ingredient 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 ingredient in aqueous suspension granules is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

[0077] 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.

[0078] 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.

[0079] 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 (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, succinyl-metolachlor, propachlor, chlorpyrifos, chlorpyrifos, naphthalenepropanoyl-methyl, R-L-naphthalenepropanoyl-methyl, propachlor, benzylthiamethoxam, bisbenzylthiamethoxam, pyrifluquinazon, chlorpyrifos, flubutyroxychlor, brobutyroxychlor, dimethoate, high-efficiency dimethoate, ethoxybenzyl-methyl, flubutyroxychlor, methoxythiamethoxam, pyrifluquinazon, isoxachlor, high-efficiency methylparaben, high-efficiency methylparaben. Acetaminophen, clethodim, butyrazosulfuron, cyprochloraz, flusulfuron, heptanosulfuron, isobutyrazosulfuron, propyzamide, terbutyrazosulfuron, methylparaben, metolachlor, methylcyclohexane, chlorpyrifos, propyzamide, pendimethalin, carbaryl, succinylmethrin, tricyclomethrin, butyrazosulfuron, succinylmethrin, bensulfuron-methyl, naphthylmethrin, acetochlor, naphthylmethrin, thiamethoxam, pyrimethanil, bensulfuron-methyl, chlorpyrifos, butyrazosulfuron, flupyrazole, atrazine, simazine, promethazine, cypermethrin, cypermethrin, atrazine, pyrazosulfuron, isopropazine, flumethrin, terbutyraz, terbutyraz, triazine flumethrin, cyprochlorazine, glyphosate, chlorpyrifos Phosphatidylcholine, Simazine, Ziziphus jujuba, Dichlorvos, Isoamyl acetate, Cyprodinil, Atrazine, Butyraz, Butyraz, Terbutaline, Methoxypropazine, Cypermethrin, Herbicides, Clonazine, Atrazine, Methoxypropazine, Glycyrrhizin, Cyanobacterium trioxide, Indaziflam, Greensulfuron, Methsulfuron-methyl, Benzylsulfuron, Chlorpyrifos, Bensulfuron-methyl, Thisulfuron-methyl, Pyrimisulfuron-methyl, Methiosulfuron-methyl, Sodium formamide sulfuron, Ethersulfuron-methyl, Etherbensulfuron-methyl, Methsulfuron-methyl, Nicosulfuron-methyl, Aminosulfuron-methyl, Acylsulfuron-methyl, Ethoxysulfuron-methyl, Cyprosulfuron-methyl, Sulfadiazine, Tetraazolidinylsulfuron, Pyrimisulfuron, Monosulfuron-methyl, Fluazolidinylsulfuron, Flupyrimisulfuron, Flupyrimisulfuron, Epimethrin Sulfuric acid, pyrazosulfuron, flusulfuron, propanil, trifluprosulfuron, sulfonylsulfuron, trifluralin, flusulfanil, trifluralin, mesosulfuron sodium salt, flupyrsulfuron, thiosulfuron, pyrimethanil, propyrisulfuron, pyrazosulfuron, trifluralin, flusulfanilamide, quizalofop-p-ethyl, ethoxysulfuron, glufosinate, bensulfuron, chlorfluazuron ethyl, methylfluzoxystrobin, trifluralin, methoxysulfuron, trifluralin, flufenoxuron, flufenoxuron, oxysulfuron, metolachlor, sulfadiazine, flufenoxuron, oxysulfuron, metolachlor, flufenoxuron, flufenoxuron, halosafen, chlormequat chloride, isoproturon, linuron, diuronSaprolegnia, fluroxypyr, bensulfuron, methyl bensulfuron, bensulfuron, sulfothiamethoxam, isoxaflutole, terbutaline, clodinafop-methyl, chlorobromosulfuron, methyl methoxysulfuron, methyl methoxysulfuron, bromosulfuron, methoxysulfuron, chlorpyrifos, metribuzin, cycloroxysulfuron, felsulfuron, flusulfuron, glufosinate, fensulfuron, cyproconazole, thiamethoxam, fensulfuron, chlorpyrifos, methamidophos, thiamethoxam, trimethourea, oxazolium, Monisouron, Anisuron, Methiuron, Chloreturon, tetraflufenozide, betaine, betaine-ethyl, betaine, sulfonamide, terbutaline, fensulfuron-methyl, fensulfuron-methyl, fensulfuron-methyl, fensulfuron-methyl, chlorpyrifos, carboxazo le, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbasulam, Butyrazosulfan, Clethodim, Metrazine, Clethodim, Wild Grass, Permethrin, Clethodim, Barnyardgrass, Cypermethrin, Oat Grass, Dimethoate, Ethylmethazine, Methiobencarb, Clethodim, Benzoate, Methiobencarb, Thionylmethazine, 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 Chloride, 2,4-D Propionic Acid, High 2,4-D Propionate, 2,4-D Butyric Acid, 2,4-D Chlorpropionic Acid, 2,4-D Propionate 2,4,5-chlorobutyric acid, 2,4,5-propylpropionic acid, 2,4,5-propylbutyric acid, 2,4,5-chloromethacin, MCPA, dicamba, 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, 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, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl In, proponitrophenol, glyphosate, barnyardphos, glufosinate, methyl parathion, glyphosate, piperazine, diammonium phosphate, dimethoate, phosmet, fenpropathrin, fenpropathrin, fenpropathrin, dimethoate, fenpropathrin, imidacloprid, imidacloprid acetic acid, imidacloprid quinolinic acid, methoxymethylene, methoxymethylene ammonium salt, imidacloprid acetic acid, imidacloprid, clopyralid, clopyralid isooctyl ester, dichloropyridine acid, aminopyridine acid, trichloropyridine acid, fluthion, haloxypyridine, trichloropyridine phenol, thiamethoxam, flupyridine, clopyralid, flupyridine hydrazone, trichloropyridine butoxyethyl ester, cliodinate, clethodim, thiamethoxam, quizalofop-p-ethyl, cyclobenzanone, butenazine, oxadiazine, pyranazine, buthidazole, cyproconazoleAmetridione, Amibuzin, bromobenzonitrile, octanoyl bromobenzonitrile, octanoyl iodobenzonitrile, iodobenzonitrile, diphenylacetonitrile, bispyribac-sodium, hydroxybispyribac-sodium, Iodobonil, pyrimisulfuron-methyl, diflubenzuron, penoxsulam, sulfadiazine, chlorpyrifos-sulfuron-methyl, dichlorvos-sulfuron-methyl, flumethrin, bispyribac-sodium, pyrimisulfuron-methyl, pyrimisulfuron-methyl, pyrimisulfuron-methyl, bispyribac-sodium, nicosulfuron-methyl, sulfadiazine, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, isoxasulfuron-methyl, isoxasulfuron-methyl, Fenoxasulfone, M ethiozolin, isopropalazine, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, bensulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flumetsulam, pyrazosulfuron, pyrazosulfuron, flumethrin, pyrazosulfuron, flupropacil, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flupropacil ... Herbicides, fluazinam, methyl methacrylate, tetrazolium chlorpyrifos, flupyridamole, chlorpyrifos, bromochlor, dimethomorph, pyrazosulfuron, cyprodinil, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, cyprodinil, pyrazosulfuron, bentazon, pyrazosulfuron, oxadiazon, cyprodinil, isoxadiazon, cyprodinil, isopropyl methoxysulfuron, cyprodinil, indicarb, sodium chlorate Herbicides, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, forage grass, bromophenol oxime, triazole sulfonate, methomyl, furazolidone, furazolidone, ethoxysulfuron, pyrimethanil, chlorpyrifos, flurfluthrin, barnyardgrass, acrolein, bensulfuron-methyl, metribuzin, oat ester, thiamethoxam, styracil, hydroxylone, methoxybenzone, pyrimethanil, chlorpyrifos, trichloropropionic acid, Al orac, Diethamquat, Etnipromid, Iprymidam, Ipfencarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapin, methylsulfuron, Cambendichlor, Cyproterinic acid, Thiamethoxam, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, pyrazole cypermethrin, furazolidone, oxadiazon, bis(oxazolyl)acrylic acid, dichloropropenylamine, fluorochloropyridinium, DOW fluorochloropyridinium, UBH-509D489, 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. ,

[0080] 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 Formula I compound 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 ingredient, but is preferably from 0.005 to 750 g ai / ha, particularly from 0.005 to 250 g ai / ha. Detailed Implementation

[0081] 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.

[0082] 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.

[0083] Table 1. Compound structures and their properties 1 H NMR

[0084] 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.

[0085] 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.

[0086] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0087] 1. Synthesis of Compound 9

[0088] (1) Weigh intermediate 9-1 (9.03 g, 54.66 mmol) into a dry flask, dissolve it in N,N-dimethylformamide, add N-iodosuccinimide (12.30 g, 54.66 mmol), and after reacting for 2 h, monitor the reaction to ensure it is complete by LC-MS. Pour the system into ice water, filter the precipitated yellow solid through a Buchner funnel, wash the filtered solid three times with water, and dry it to obtain intermediate 9-2 (10.00 g of yellow solid, yield 61.02%, purity 90%).

[0089] (2) Weigh intermediate 9-2 (10.00 g, 34.35 mmol) into a dry eggplant-shaped flask, dissolve it in dichloromethane, add 2-(7-azabenzotriazole)-N,N,N',N'-tetramethylurea hexafluorophosphate (19.59 g, 51.53 mmol), N,N-diisopropylethylamine (8.88 g, 68.71 mmol) and aniline (3.84 g, 41.22 mmol), and react at room temperature overnight. After LC-MS monitoring showed no significant change in the reaction, pour the system into water, add dichloromethane for extraction, combine the organic phases, dry with anhydrous Na2SO4, concentrate the organic phase, and purify it using an EA / PE (10-50%) system via Flash to obtain intermediate 9-3 (7.50 g yellow solid, yield 59.62%, purity 97%).

[0090] (3) Weigh intermediate 9-3 (3.00 g, 8.19 mmol) into a dry eggplant-shaped flask, dissolve it in N,N-dimethylformamide, cool the reaction system in an ice bath, slowly add trifluoroacetic anhydride (1.72 g, 7.19 mmol), remove the ice bath and restore the reaction to room temperature. After 1 h of reaction, monitor the reaction to ensure it is complete by LC-MS, pour the system into ice water, filter the precipitated yellow solid through a Buchner funnel, wash the filtered solid three times with water, and dry it to obtain intermediate 9-4 (3.40 g of yellow solid, yield 89.97%, purity 93%).

[0091] (4) Weigh intermediate 9-4 (3.40 g, 7.36 mmol) into a dry eggplant-shaped flask. Using toluene as solvent, add p-toluenesulfonic acid (1.27 g, 7.36 mmol) and dry molecular sieve. After refluxing for 4 h, monitor the reaction by LC-MS until it is complete. Remove toluene, add water and ethyl acetate for extraction, dry the organic phase with anhydrous Na2SO4, concentrate the organic phase, and purify the residue with EA / PE (0-10%) system using Flash to obtain intermediate 9-5 (3.20 g yellow solid, yield 97.93%, purity 98%).

[0092] (5) Weigh intermediate 9-5 (1.5 g, 3.38 mmol) into a dry eggplant-shaped flask, dissolve it in tetrahydrofuran, add nitrogen protection, cool the reaction system in an ice bath, slowly add 2M isopropyl magnesium chloride tetrahydrofuran solution (2.53 mL, 5.07 mmol), keep the reaction in an ice bath for 30 min, then introduce carbon dioxide gas, monitor the reaction for completeness by LC-MS, add saturated ammonium chloride aqueous solution to quench the reaction, add ethyl acetate for extraction, combine the organic phases and dry with anhydrous Na2SO4, remove the organic phase to obtain intermediate 9-6 (yellow solid 920 mg, yield 75.20%, purity 85%).

[0093] (6) Weigh intermediate 9-6 (920 mg, 2.54 mmol) into a dry eggplant-shaped flask, dissolve it in dichloromethane, add oxalyl chloride (644 mg, 5.08 mmol), add 2-3 drops of N,N-dimethylformamide as a catalyst, react for 30 min, remove the solvent from the system by rotary evaporation, and dissolve the obtained solid in an appropriate amount of dichloromethane for later use;

[0094] In a separate dry, round-bottomed flask, 1,3-cyclohexanedione (341 mg, 3.05 mmol) was placed in and dissolved in dichloromethane. Triethylamine (513 mg, 5.08 mmol) was then added. The reaction system was cooled in an ice bath, and the prepared solution was slowly added dropwise to the system. The ice bath was removed, and the reaction was allowed to proceed at room temperature. When the reaction was no longer observed by LC-MS, water and dichloromethane were added for extraction. The combined organic phases were dried over anhydrous Na2SO4 and purified by Flash using an EA / PE (10-30%) system to obtain intermediate 9-7 (623 mg of yellow solid, yield 53.75%, purity 97%).

[0095] (7) Weigh intermediate 9-7 (623 mg, 1.36 mmol) into a dry flask, dissolve it in dichloromethane, add triethylamine (207 mg, 2.05 mmol) and acetone cyanohydrin (11.62 mg, 0.14 mmol), and react overnight at room temperature. When the reaction stops as monitored by LC-MS, add water and dichloromethane for extraction, combine the organic phases and dry with anhydrous Na2SO4. The target compound 9 (121 mg yellow solid, yield 19.42%, purity 99%) is obtained by Flash purification using an ACN / H2O (10-30%) system.

[0096] 2. Synthesis of Compound 57

[0097] (1) Compound 9-2 (10.00 g, 34.35 mmol) was dissolved in 10 mL of dichloromethane, and 2-(7-azabenzotriazole)-N,N,N',N'-tetramethylurea hexafluorophosphate (19.59 g, 51.53 mmol), N,N-diisopropylethylamine (8.88 g, 68.71 mmol) and cyclopropylamine (3.84 g, 41.22 mmol) were added. The mixture was reacted overnight at room temperature. After no significant change was observed in the reaction as monitored by LC-MS, the system was poured into water, extracted with dichloromethane, and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated, and the system was purified by normal phase to obtain 57-1 (7.50 g of yellow solid, yield 66%).

[0098] (2) At room temperature, compound 57-1 (2.0 g, 6.0 mmol) was dissolved in 5 mL of dichloromethane. While stirring, triethylamine (0.9 g, 9.0 mmol) and acetyl chloride (0.7 g, 9.0 mmol) were slowly added. After the addition was complete, stirring was continued for 2 h. LCMS monitoring showed that the reaction of the starting material was basically complete, and the main peak was the product peak. After concentrating the organic phase, a light yellow crude compound 57-2 was obtained, which was directly used in the next step.

[0099] (3) At room temperature, the crude product 57-2 from the previous step was dissolved in 10 mL of toluene, and p-toluenesulfonic acid (1.6 g, 9.0 mmol) was added. After the addition was complete, the mixture was stirred at 120 °C overnight. After the reaction was completed, 50 mL of water was added, and the organic phases were extracted with ethyl acetate and combined. The concentrated organic phase was separated by column chromatography to obtain a white solid compound 57-3 (0.8 g, 15%).

[0100] (4) At room temperature, compound 57-3 (0.8 g, 2.3 mmol) was dissolved in 10 mL of N,N-dimethylformamide, and lithium formate (230 mg, 4.5 mmol), lithium chloride (190 mg, 4.5 mmol), acetic anhydride (710 mg, 6.9 mmol) and N,N-diisopropylethylamine (890 mg, 6.9 mmol) were added sequentially. After purging with nitrogen three times, (2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) chloride (35 mg, 0.05 mmol) was quickly added. After the addition was complete, the mixture was purged with nitrogen three times and stirred overnight at 70 °C. LCMS monitoring showed that the raw material was almost completely consumed and the main peak was the product peak. After adding 20 mL of water to the reaction solution, the mixture was extracted with ethyl acetate. The pH of the aqueous phase was adjusted to acidic with dilute hydrochloric acid. The organic phase was concentrated to obtain crude yellow solid compound 57-4 (500 mg, 81%).

[0101] (5) At room temperature, compound 57-4 (500 mg, 1.8 mmol) was dissolved in 5 mL of dichloromethane, and 1,3-cyclohexanedione (310 mg, 2.7 mmol) and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (530 mg, 2.7 mmol) were added sequentially. After the addition was complete, the mixture was stirred at room temperature for 1 h. After the reaction was completed, the mixture was quenched with water and extracted with ethyl acetate. The combined organic phases were washed with saturated brine and dried over anhydrous sodium sulfate. The organic phase was then evaporated to dryness to obtain crude compound 57-5, which was a light yellow oil. The crude product was used directly in the next step.

[0102] (6) At room temperature, the crude product 57-5 from the previous step was dissolved in 10 mL of acetonitrile, and triethylamine (550 mg, 5.4 mmol) and a catalytic amount of acetone cyanohydrin were added sequentially. After the addition was complete, the mixture was replaced with N2 three times and then heated to 60 °C and stirred overnight. After the reaction was completed, it was quenched with dilute hydrochloric acid, extracted with dichloromethane, and the organic phases were combined. After concentrating the organic phase, the crude product was separated by column chromatography to obtain a white solid compound 57 (100 mg, 20%).

[0103] 3. Synthesis of Compound 62

[0104] (1) In a 100 mL single-necked flask, 62-1 (3 g, 1.0 eq, 13.6 mmol) was added to 30 mL of ethanol, followed by the addition of elemental iodine (6.8 g, 2.0 eq, 27.2 mmol). The reaction was carried out at room temperature for 8 h. The reaction was monitored by LCMS to indicate completion. After removing the solvent, the product was extracted with ethyl acetate and water, and then subjected to column chromatography to obtain product 62-2 (3 g, yield 63%).

[0105] (2) In a 250 mL single-necked flask, 62-2 (3.0 g, 1.0 eq, 8.7 mmol) was added to 30 mL of dichloromethane, followed by the addition of n-propylamine (0.76 g, 1.5 eq, 13.0 mmol), 2-(7-azabenzotriazole)-N,N,N',N'-tetramethylurea hexafluorophosphate (4.9 g, 1.5 eq, 13.0 mmol), and N,N-diisopropylethylamine (2.2 g, 2.0 eq, 17.4 mmol). The reaction was carried out at room temperature for 8 h. The reaction was monitored by LCMS until completion. After post-treatment, dichloromethane and water were added for extraction, and the product was dried and purified under normal phase to obtain product 62-3 (2.5 g, yield 75%).

[0106] (3) In a 100 mL single-necked flask, 62-3 (2.5 g, 1.0 eq, 6.4 mmol) was added to 20 mL of tetrahydrofuran, followed by trifluoroacetic anhydride (2.0 g, 1.5 eq, 9.6 mmol). The reaction was carried out at room temperature for 2 h. The reaction was monitored by LCMS until completion. After post-treatment, ethyl acetate and water were added for extraction, and the product was dried to obtain product 62-4 (2.7 g, 90% yield).

[0107] (4) In a 100 mL single-necked flask, 62-4 (2.7 g, 1.0 eq, 5.6 mmol) was added to 15 mL of 1,2-dichloroethane, followed by trifluoroacetic acid (0.95 g, 1.5 eq, 8.4 mmol). The reaction was carried out at 140 °C for 8 h. The reaction was confirmed by LCMS. After post-treatment, the product was extracted with dichloromethane and water, dried, and purified under normal phase to obtain product 62-5 (2.7 g, yield 92%).

[0108] (5) In a 100 mL single-necked flask, add 62-5 (2.7 g, 1.0 eq, 5.8 mmol) to 20 mL of water. Lithium formate (452 ​​mg, 1.5 eq, 8.7 mmol), lithium chloride (365 mg, 1.5 eq, 8.7 mmol), acetic anhydride (1.2 g, 2.0 eq, 11.6 mmol), N,N-diisopropylethylamine (1.4 g, 2.0 eq, 11.6 mmol), and an appropriate amount of catalyst (2-dicyclohexylphosphino-2′,4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1′-biphenyl)]palladium(II) chloride (35 mg, 0.05 mmol) were added sequentially to N,N-dimethylformamide. The reaction was carried out at 80 °C for 3 h. The reaction was monitored by LCMS until completion. Water was added to the post-treatment reaction solution, the pH was adjusted, back-extracted, dried, and filtered to obtain product 62-6 (2.0 g, yield 90%).

[0109] (6) Dissolve product 62-6 from the previous step in 5 mL of dichloromethane, add oxalyl chloride (200 mg, 1.2 eq, 1.56 mmol), and react at room temperature for 1 hour to prepare acyl chloride. Add this to a dichloromethane reaction system containing 1,3-cyclohexanedione (175 mg, 1.2 eq, 1.56 mmol) and triethylamine (393 mg, 3 eq, 3.9 mmol), and react at room temperature for 4 hours. Monitor the reaction completion by LCMS. For post-treatment, extract with dichloromethane and water, wash with acid, dry, and filter to obtain product 62-7 (300 mg, yield 48%).

[0110] (7) In a 50 mL single-necked flask, 62-7 (300 mg, 1.0 eq, 0.63 mmol) was added to 20 mL of acetonitrile, followed by triethylamine (190 mg, 3.0 eq, 1.89 mmol) and an appropriate amount of acetone cyanohydrin. The reaction was carried out at 40 °C for 8 h. After the reaction was completed by LCMS monitoring, dichloromethane and water were added for extraction, followed by acid washing and reverse-phase purification to obtain product 62 (70 mg, yield 22%).

[0111] Bioactivity evaluation:

[0112] The activity level standards for plant damage (i.e., growth control rate) are as follows:

[0113] Level 9: Complete death;

[0114] Level 8: Growth control rate is greater than or equal to 90% and less than 100%;

[0115] Level 7: Growth control rate is greater than or equal to 80% and less than 90%;

[0116] Level 6: Growth control rate is greater than or equal to 70% and less than 80%;

[0117] Level 5: Growth control rate is greater than or equal to 50% and less than 70%;

[0118] Level 4: Growth control rate is greater than or equal to 30% and less than 50%;

[0119] Level 3: Growth control rate greater than or equal to 20% and less than 30%;

[0120] Level 2: Growth control rate greater than or equal to 10% and less than 20%;

[0121] Level 1: Growth control rate less than 10%;

[0122] Level 0: No effect.

[0123] The above growth control rates are fresh weight control rates.

[0124] (1) Post-emergence testing experiment:

[0125] Seeds of monocot and dicot weeds, as well as seeds of major crops, were placed in plastic pots filled with soil and 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 tested compound of this invention was dissolved in acetone, and then Tween 80 was added. Methyl oleate emulsifiable concentrate at 1.5 L / ha was used as a synergist, and the solution was diluted with water to a specific concentration. The solution was then sprayed onto the plants using a spray tower. After three weeks of cultivation in the greenhouse following application, the weed control effect was statistically analyzed. The experiment was repeated three times, and the average value was taken. Representative data are listed in Table 2.

[0126] Table 2 Results of post-emergence weed control experiment

[0127] Table 3 Comparison of Post-emergence Weed Trial Results

[0128] Note: N represents no data; control compound A:

[0129] The results show that, compared with control compound A, the compound described in this application can significantly improve crop safety and has better selectivity while maintaining or improving herbicidal activity.

[0130] (2) Water-based closed-loop test:

[0131] Sow weed or crop seeds evenly in muddy soil, let stand in the greenhouse for 1-3 days, then apply the pesticide using a mobile sprayer. Repeat the application three times. After application, keep the soil in muddy state and continue cultivation for about 14 days to observe the weed emergence. The control efficacy is evaluated and statistically analyzed. Representative data are listed in Table 4.

[0132] Table 4 Results of the Water Direct Streaming Closed Test

[0133] Note: N represents no data.

[0134] Furthermore, numerous tests have revealed that the compounds and compositions described in this invention can control many key grass and broadleaf weeds. Tests on wheat, rice, peanuts, and other crops under different application methods have also demonstrated excellent selectivity and commercial value.

[0135] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit it. Although the present invention has been described in detail with reference to preferred embodiments, those skilled in the art should understand that modifications or equivalent substitutions can be made to the technical solutions of the present invention without departing from the spirit and scope of the present invention.

Claims

1. A quinazolinone compound as shown in general formula I, or a salt thereof: in, Q represents a heterocyclic group. R1, R2, R4, and R6 independently represent hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, and -OR, respectively. 21 -(CO)OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 ; R3 represents unsubstituted or selected from cyano, nitro, halogen, -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 An alkyl group substituted with at least one group; R5 and R7 independently represent alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclic, or are selected from cyano, nitro, halogen, cycloalkyl, aryl, heterocyclic, -(CO)OR 21 -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 An alkyl, alkenyl, or ynyl group substituted with at least one group; X1, X2, X3, X4, X5, and X6 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, or cycloalkylalkyl, or two substituents on the same carbon atom connected to form unsubstituted or halogen-substituted -(CH2)2-, -(CH2)3-, -(CH2)4-, or -(CH2)5-, or two substituents on different carbon atoms connected to form -O-, or unsubstituted or halogen-substituted -CH2-, -(CH2)2-, -(CH2)3-, or -(CH2)4-; R 21 Each of these can independently represent hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclic or heterocyclic alkyl. The aforementioned cycloalkyl, cycloalkenyl, heterocyclic, or aryl groups are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 The aryl group is substituted by at least one group in 2, or the two adjacent carbon atoms on the aryl group are connected to an unsubstituted or halogen-substituted -O-CH2-O- to form a fused ring; R 10 Each can independently represent hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, or haloalkynyl.

2. A quinazolinone compound or a salt thereof according to claim 1, characterized in that, R1, R2, R4, and R6 independently represent hydrogen, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, aryl, heterocyclic, and -OR, respectively. 21 -(CO)OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 ; R3 represents unsubstituted or selected from cyano, nitro, halogen, -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 C1-C8 alkyl groups substituted with at least one group; R5 and R7 independently represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, aryl, heterocyclic, or groups selected from cyano, nitro, halogen, C3-C8 cycloalkyl, aryl, heterocyclic, and -(CO)OR. 21 -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl groups substituted with at least one group; X1, X2, X3, X4, X5, and X6 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl or C3-C8 cycloalkyl-C1-C8 alkyl, or two substituents on the same carbon atom connected to form unsubstituted or halogen-substituted -(CH2)2-, -(CH2)3-, -(CH2)4- or -(CH2)5-, or two substituents on different carbon atoms connected to form -O-, or unsubstituted or halogen-substituted -CH2-, -(CH2)2-, -(CH2)3- or -(CH2)4-; R 21 Each of these can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl-C1-C8 alkyl, aryl, aryl-C1-C8 alkyl, heterocyclic or heterocyclic-C1-C8 alkyl; The aforementioned C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic, or aryl groups are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 ) 20 At least one group in the aryl group is substituted, or two adjacent carbon atoms on the aryl group are connected to an unsubstituted or halogenated -O-CH2-O- to form a fused ring; R 10 Each of these can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, or halo-C2-C8 alkynyl.

3. A quinazolinone compound or a salt thereof according to claim 1 or 2, characterized in that, R1, R2, R4, and R6 independently represent hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, aryl, heterocyclic, and -OR, respectively. 21 -(CO)OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 ; R3 represents unsubstituted or selected from cyano, nitro, halogen, -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 C1-C6 alkyl groups substituted with at least one group; R5 and R7 independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, aryl, heterocyclic, or groups selected from cyano, nitro, halogen, C3-C6 cycloalkyl, aryl, heterocyclic, and -(CO)OR. 21 -OR 21 -SR 21 -(SO)R 21 or -(SO2)R 21 C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl groups substituted with at least one group; X1, X2, X3, X4, X5, and X6 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl-C1-C6 alkyl, or two substituents on the same carbon atom connected to form unsubstituted or halogenated -(CH2)2-, -(CH2)3-, -(CH2)4- or -(CH2)5-, or two substituents on different carbon atoms connected to form -O-, or unsubstituted or halogenated -CH2-, -(CH2)2-, -(CH2)3- or -(CH2)4-; R 21 Each of these can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heterocyclic or heterocyclic-C1-C6 alkyl; The aforementioned C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, or aryl groups are each independently unsubstituted or 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, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 ) 20 At least one group in the aryl group is substituted, or two adjacent carbon atoms on the aryl group are connected to an unsubstituted or halogenated -O-CH2-O- to form a fused ring; R 10 Each of these can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, or halo-C2-C6 alkynyl.

4. A quinazolinone compound or a salt thereof according to any one of claims 1-3, characterized in that, It is selected from any one of the options in Table 1.

5. A method for preparing a quinazolinone compound or a salt thereof as described in any one of claims 1-4, characterized in that, Includes the following steps: With compounds The reaction is carried out as an intermediate, wherein L represents a leaving group (such as OH, halogen, p-nitrophenoxy or cyano, etc.), and the substituents R1, R2, R3, R4 and R5 are defined as described in any one of claims 1-4.

6. The preparation method according to claim 5, characterized in that, (1) When Q represents Compound IV-1 is prepared by a condensation reaction of the compound represented by general formula II and the compound represented by general formula III-1, and then compound I-1 is prepared by a rearrangement reaction. The reaction equation is as follows: (2) When Q represents Compound I-2 is prepared by a condensation reaction of the compound represented by general formula II and the compound represented by general formula III-2, and the reaction equation is as follows: (3) When Q represents Compound I-3 is prepared by a condensation reaction of the compound represented by general formula II and the compound represented by general formula III-3, and the reaction equation is as follows: The definitions of Y1, Y2, Y3, Y4, Y5, Y6, R1, R2, R3, R4, R5, R6, and R7 are as described in claims 1-4. Preferably, the condensation reactions in step 1, reaction (2) and (3) are all carried out in the presence of a solvent, and / or the rearrangement reaction in step 2 is carried out in the presence of a catalyst (such as acetone cyanohydrin), a base and a solvent. More preferably, a condensing agent and / or a base are added to the condensation reactions in step 1, reaction (2) and (3); More preferably, the solvents are all selected from at least one of aromatic hydrocarbons, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dichloroethane, dimethyl sulfoxide, 1,4-dioxane, dichloromethane, or ethyl acetate; the bases are all selected from at least one of inorganic or organic bases; and / or the condensing agents in step 1, reaction (2), and (3) are respectively selected from at least one of benzotriazol-1-yl-oxytripyrrolidinephosphine hexafluorophosphate, N,N'-carbonyldiimide, 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxybenzotriazole, 1,3-dicyclohexylcarbodiimide, or N,N,N',N'-tetramethyl-O-(7-azabenzotriazol-1-yl)hexafluorophosphate urea.

7. A herbicide composition, characterized in that, The herbicide includes at least one of the quinazolinone compounds or their salts as described in any one of claims 1-4, and preferably, also includes a formulation adjuvant.

8. A method for controlling weeds, characterized in that, This includes applying an effective amount of at least one of the quinazolinone compounds or their salts as described in any one of claims 1-4, or the herbicide composition as described in claim 7, to plants or weedy areas.

9. Use of at least one of the quinazolinone compounds or their salts as described in any one of claims 1-4 or the herbicide composition as described in claim 7 for weed control, preferably, the quinazolinone compounds or their salts are used to control weeds in useful crops, more preferably, the useful crops include transgenic crops or crops treated with genome editing technology.

10. An intermediate as described in Formula II of claim 5.

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