Pyrazole pyrimidine compound and preparation method therefor, herbicidal composition, and use

Abstract

Provided are a pyrazole pyrimidine compound and a preparation method therefor, a herbicidal composition, and a use, relating to the technical field of pesticides. The compound is as shown in general formula I: wherein X represents halogen, -OX1, -(CO)OX2, -(CO)SX2, or -(CO)N(X2)2; X1 represents hydrogen, alkyl, alkenyl, alkynyl, or the like; X2 independently represents hydrogen, alkyl, alkenyl, alkynyl, or the like; and Y, Z, R1, R2, R3, R4, R5, R6, R7, and R8 each independently represent hydrogen, halogen, cyano, or the like. The compound has excellent herbicidal activity and crop safety.

Description

Pyrazole pyrimidine compound, preparation method thereof, herbicide composition and application thereof Technical Field

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

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

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

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

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

[0006] wherein X represents halogen, -OX1, -(CO)OX2, -(CO)SX2 or -(CO)N(X2)2;

[0007] X1 represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, -(CO)R9, -(CO)N(R9)2, -(CO)N(R9)(OR9) or -(CO)OR9, wherein the alkyl, alkenyl or alkynyl group is optionally selected from halogen, cycloalkyl, aryl, heterocyclyl, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2;

[0008] X2 independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclic group, wherein the alkyl, alkenyl or alkynyl group is optionally selected from halogen, cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2;

[0009] Y, Z, R1, R2, R3, R4, R5, R6, R7, and R8 independently represent hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclic, -OR9, -(CO)R9, -(CO)OR9, -(CO)N(R9)2, -CR9=N-OR9, -S(O) n R9 or -N(R9)2, the alkyl, alkenyl or alkynyl group is optionally selected from halogen, cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)OR9, -S(O) n R9 or -N(R9)2 is substituted by at least one group, or Y and Z together form -CH=CH-CH=CH-, or R6 and R7 together form -OCH2O- which is unsubstituted or substituted by halogen;

[0010] n is 0, 1, or 2;

[0011] R9 each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, wherein the alkyl, alkenyl or alkynyl group is optionally substituted by at least one group selected from halogen or alkoxy;

[0012] The aforementioned "cycloalkyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR 10 、-SR 10 、-(CO)R 10 、-(CO)OR 10 、-(CO)N(R 10 )2、-(CS)N(R 10 )2、-(SO)R 10 or -(SO2)R 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure;

[0013] R 10 Each of them is independently hydrogen, alkyl, haloalkyl, aryl or heterocyclic group which is unsubstituted or substituted by at least one group selected from halogen and alkyl.

[0014] In a specific embodiment, X1 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, aryl, heterocyclyl, -(CO)R9, -(CO)N(R9)2, -(CO)N(R9)(OR9) or -(CO)OR9, wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally selected from halogen, C3-C8 cycloalkyl, aryl, heterocyclyl, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2;

[0015] X2 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, aryl or heterocyclic group, wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally selected from halogen, C3-C8 cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2;

[0016] Y, Z, R1, R2, R3, R4, R5, R6, R7, and R8 independently represent hydrogen, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)R9, -(CO)OR9, -(CO)N(R9)2, -CR9=N-OR9, -S(O) n R9 or -N(R9)2, the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally selected from halogen, C3-C8 cycloalkyl, aryl, heterocyclyl, -OR9, -(CO)OR9, -S(O) n R9 or -N(R9)2 is substituted by at least one group, or Y and Z together form -CH=CH-CH=CH-, or R6 and R7 together form -OCH2O- which is unsubstituted or substituted by halogen;

[0017] R9 each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, aryl, arylC1-C8 alkyl, heterocyclyl or heterocyclylC1-C8 alkyl, wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally substituted by at least one group selected from halogen or C1-C8 alkoxy;

[0018] The aforementioned "C3-C8 cycloalkyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, -OR 10 、-SR 10 、-(CO)R 10 、-(CO)OR 10 、-(CO)N(R 10 )2、-(CS)N(R 10 )2、-(SO)R 10 or -(SO2)R 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure;

[0019] R 10 Each is independently hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, aryl or heterocyclic group which is unsubstituted or substituted with at least one group selected from halogen and C1-C8 alkyl.

[0020] In another embodiment, X1 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, aryl, heterocyclyl, -(CO)R9, -(CO)N(R9)2, -(CO)N(R9)(OR9) or -(CO)OR9, wherein the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally selected from halogen, C3-C6 cycloalkyl, aryl, heterocyclyl, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2;

[0021] X2 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, aryl or heterocyclic group, and the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally selected from halogen, C3-C6 cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2;

[0022] Y, Z, R1, R2, R3, R4, R5, R6, R7, and R8 independently represent hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)R9, -(CO)OR9, -(CO)N(R9)2, -CR9=N-OR9, -S(O) n R9 or -N(R9)2, the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally selected from halogen, C3-C6 cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)OR9, -S(O) n R9 or -N(R9)2 is substituted by at least one group, or Y and Z together form -CH=CH-CH=CH-, or R6 and R7 together form -OCH2O- which is unsubstituted or substituted by halogen;

[0023] R9 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, aryl, arylC1-C6 alkyl, heterocyclyl or heterocyclylC1-C6 alkyl, wherein the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally substituted by at least one group selected from halogen or C1-C6 alkoxy;

[0024] The aforementioned "C3-C6 cycloalkyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, -OR 10 、-SR 10 、-(CO)R 10 、-(CO)OR 10 、-(CO)N(R 10 )2、-(CS)N(R 10 )2、-(SO)R 10 or -(SO2)R 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure;

[0025] R 10 Each is independently hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, aryl or heterocyclic group which is unsubstituted or substituted with at least one group selected from halogen and C1-C6 alkyl.

[0026] In another embodiment, the following compounds are excluded:

[0027] 5-[(5-chloro-2-pyrimidinyl)hydroxymethyl]-1-(3,4-difluorophenyl)-1H-pyrazole-3-carbonitrile;

[0028] 5-chloro-α-[3-(difluoromethyl)-1-(3,4-difluorophenyl)-1H-pyrazol-5-yl]-2-pyrimidinyl acetate;

[0029] 5-bromo-α-[3-(trifluoromethyl)-1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl]-2-pyrimidinyl acetate;

[0030] 5-chloro-α-[3-(trifluoromethyl)-1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl]-2-pyrimidinyl acetate;

[0031] α-(1-phenyl-1H-pyrazol-5-yl)-2-pyrimidinemethanol;

[0032] 5-Methyl-α-(1-phenyl-1H-pyrazol-5-yl)-2-pyrimidinemethanol.

[0033] In the definitions of the compounds represented by the above general formula and in all the following structural formulas, the technical terms used, whether used alone or in compound terms, represent the following substituents: Alkyl groups having more than two carbon atoms may be straight-chain or branched. For example, in the compound term "cycloalkylalkyl," the alkyl group may be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. Alkyl groups include, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl, such as n-propyl or isopropyl; C4 alkyl-butyl, such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl, such as n-pentyl; and C6 alkyl-hexyl, such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, vinyl, allyl, 1-methylprop-2-ene-1-yl, 2-methylprop-2-ene-1-yl, but-2-ene-1-yl, but-3-ene-1-yl, 1-methylbut-3-ene-1-yl and 1-methylbut-2-ene-1-yl. Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds can be at any position of each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system with, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl with, for example, three to six carbocyclic ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein double bonds can be at any position. Halogen is fluorine, chlorine, bromine or iodine.

[0034] Unless otherwise specified, the "aryl" mentioned in the present invention includes but is not limited to phenyl, naphthyl, The "heterocyclic group" includes but is not limited to saturated or unsaturated non-aromatic cyclic groups etc., and also include but are not limited to heteroaryl, i.e. an aromatic cyclic group containing, for example, 3 to 6 ring atoms and optionally fused to a benzo ring, wherein 1 to 4 (e.g. 1, 2, 3 or 4) heteroatoms in the ring atoms are selected from oxygen, nitrogen and sulfur, for example

[0035] The term "optional" or "optionally" means that the subsequently described event or circumstance may or may not occur, and that the description includes instances where the event or circumstance occurs and instances where the event or circumstance does not occur. For example, the term "optionally substituted with" means that the specified atom or group is unsubstituted or substituted with one or more substituents. If a group is substituted with a group, this should be understood to mean that the group is substituted with one or more identical or different groups selected from those mentioned. In addition, identical or different substitution characters contained in identical or different substituents are independently selected and may be the same or different. The same applies to ring systems formed from different atoms and units. At the same time, the scope of the claims will exclude compounds that are known to those skilled in the art to be chemically unstable under standard conditions.

[0036] In addition, unless otherwise specified, the term "substituted by at least one group" as used herein refers to being substituted by 1, 2, 3, 4 or 5 groups; groups (including heterocyclic groups, aryl groups, etc.) without a specific connection position can be connected at any position, including the position connected to C or N; if it is substituted, the substituent can also be substituted at any position as long as it complies with the chemical bond connection rules. For example, a heteroaryl group substituted by 1 methyl group Can represent wait.

[0037] If various functional groups are present, the present invention also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0038] Stereoisomers can be obtained from the mixture obtained in the preparation by optical resolution. Stereoisomers can also be selectively prepared by using stereoselective reactions and optically active starting materials and / or auxiliary agents. For optical resolution, conventional methods (see Textbooks of Stereochemistry) can usually be used, such as the following methods for separating the mixture into diastereomers, such as physical methods, such as crystallization, chromatography, especially column chromatography and high pressure liquid chromatography, optionally distillation methods under reduced pressure, extraction methods and other methods, usually using chromatographic separation on a chiral solid phase, which can separate the residual mixture of enantiomeric structures. Suitable for preparation or for industrial scale is such a method, such as crystallization of diastereomeric salts, which can be obtained from compounds using optically active acids, and if an acidic group is present, optically active bases can be used as needed.

[0039] The preparation method of the pyrazole pyrimidine compound comprises the following steps:

[0040] When X represents -(CO)OX2, -(CO)SX2 or -(CO)N(X2)2, the compound represented by the general formula II is reacted with the compound represented by the general formula III to obtain the compound represented by the general formula I, and the reaction equation is as follows:

[0041] When X represents halogen or -OX1, the compound shown in formula IV React with the compound shown in formula III to obtain the compound shown in formula I' Then the target compound is obtained through conventional substitution reaction;

[0042] Alternatively, when X represents a halogen, Prepared by halogenation reaction;

[0043] wherein L represents a halogen, and the substituents X, R1, R2, R3, R4, R5, R6, R7, R8, Y and Z are as defined above.

[0044] In one embodiment, the reaction for preparing the compound of formula I or I' is carried out in the presence of a base and a solvent.

[0045] In another embodiment, the base is selected from at least one of an inorganic base (such as NaOH, KOH, KF, NaH or KH, etc.) or an organic base (such as n-butyl lithium, tert-butyl lithium or sodium tert-butoxide, etc.).

[0046] In another embodiment, the solvent is selected from at least one of toluene, dichloroethane, dimethyl sulfoxide, acetonitrile, ethyl acetate, diethyl ether, hexane or tetrahydrofuran.

[0047] In one embodiment, the halogenation reaction is carried out in the presence of a solvent, a halogenating agent and an initiator.

[0048] In another embodiment, the solvent is selected from at least one of carbon tetrachloride, acetonitrile, dichloromethane, trifluorotoluene or benzene.

[0049] In another specific embodiment, the halogenating agent is selected from at least one of NBS, NCS, Br2, chlorine, I2 or thionyl chloride.

[0050] In another embodiment, the initiator is selected from at least one of AIBN, benzoyl peroxide, DTBP or photoinitiator.

[0051] In addition, the compounds of the present invention can be prepared by referring to the methods shown in WO2023099354A and the like.

[0052] A herbicide composition comprises a herbicidally effective amount of at least one of the pyrazolopyrimidine compounds; preferably, further comprises a formulation adjuvant; more preferably, further comprises other active ingredients.

[0053] A method for controlling weeds comprises applying a herbicidally effective amount of at least one of the pyrazolopyrimidine compounds or the herbicide composition on plants or weedy areas.

[0054] The use of at least one of the pyrazolopyrimidine compounds or the herbicide composition in controlling weeds, preferably, the pyrazolopyrimidine compound is used to control weeds in useful crops, wherein the useful crops are transgenic crops or crops treated with genome editing technology.

[0055] An intermediate is represented by formula II.

[0056] An intermediate is represented by formula IV.

[0057] The compounds of formula I of the present invention have outstanding herbicidal activity against many economically important monocotyledonous and dicotyledonous harmful plants. The active substances of the present invention are also effective against perennial weeds that grow from rhizomes, rootstocks, or other perennial organs and are difficult to control. In this regard, it is generally unimportant whether the substance is used before sowing, before germination, or after germination. Representative examples of monocotyledonous and dicotyledonous weed groups that can be controlled by the compounds of the present invention are mentioned in particular, without being limited to specific species. Examples of weed species on which the active substances are effective include monocotyledonous plants: annual Avena, Secale, Grass, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria, and Cyperus, and perennial Agropyron, Cyperus, Imperata, and Sorghum, as well as perennial Cyperus.

[0058] Regarding dicotyledonous weed species, its activity extends to species such as annual Galium, Viola, Veronica, Sesame, Chickweed, Amaranthus, Sinapsis, Ipomoea, Glechoma, Matricaria, and Abutilon, as well as perennial weeds such as Convolvulus, Thistle, Rumex, and Artemisia. The active ingredients of the present invention effectively control harmful plants such as Echinochloa, Sagittaria, Alisma, Eriocheir, Saccharum, and Cyperus under unspecified conditions during rice sowing. If applied to the soil surface before germination, the weed seedlings can be completely prevented from emerging, or growth can be halted as soon as the cotyledons emerge, ultimately resulting in complete death after three to four weeks. The compounds of the present invention are particularly active against Apia, Sesame, Polygonum convolvulus, Chickweed, Ivy-leaved Veronica, Veronica arabicum, Pansy, Amaranthus, Galium, and Kochia.

[0059] While the compounds of the present invention exhibit excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they cause no damage, or only minimal damage, to economically important crop plants such as wheat, barley, rye, rice, corn, sugar beets, cotton, and soybeans. They are particularly compatible with cereal crops such as wheat, barley, and corn, particularly wheat. Therefore, the compounds of the present invention are well suited for selectively controlling undesirable plants in agricultural or ornamental crops.

[0060] Due to their herbicidal properties, these active substances can be used to control harmful plants in known or upcoming genetically engineered plant cultivation. Transgenic plants often possess superior properties, such as resistance to specific pesticides, especially herbicides, or resistance to plant diseases or their causative microorganisms, such as specific insects or fungal, bacterial, or viral microorganisms. Other specific properties are related to the product's characteristics, such as quantity, quality, storage stability, composition, and specific ingredients. Thus, transgenic plant products are known to be obtained with increased starch content, improved starch quality, or a different fatty acid composition.

[0061] The compounds of formula I according to the present invention or their salts are preferably used in the cultivation of economically important genetically modified crops and ornamental plants, for example cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn, or in the cultivation of sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetable plants. The compounds of formula I are preferably used in the cultivation of useful plants with herbicides which are resistant or have been rendered resistant to the toxic effects of the herbicides by genetic engineering.

[0062] Conventional methods for breeding plants with improved traits compared to known plants include, for example, conventional mating methods and mutant breeding. In other words, new plants with improved traits can be obtained by means of genetic engineering methods (see, for example, EP-0221044 A, EP-0131624 A). For example, several methods have been described:

[0063] - genetic engineering of crop plants to improve starch synthesis in plants (e.g. WO 92 / 11376, WO 92 / 14827, WO 91 / 19806);

[0064] - transgenic crop plants resistant to specific herbicides, such as glufosinate herbicides (e.g. EP-0242236 A, EP-0242246 A) or glyphosate herbicides (WO 92 / 00377), or sulfonylurea herbicides (EP-0257993 A, US Pat. No. 5,013,659 A);

[0065] - genetically modified crop plants, such as cotton, that produce Bacillus thuringiensis toxins (Bt toxins) that protect against attack by certain pests (EP-0142924 A, EP-0193259 A);

[0066] - Transgenic crop plants with improved fatty acid composition (WO 91 / 13972).

[0067] Numerous molecular biotechniques are known for producing transgenic plants with improved traits (see, for example, Sambrook et al., 1989, Molecular Amplification, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York; or Winnacker, "Gene und Klone," VCH Weinheim, 2nd ed., 1996, or Christou, "Trends in Plant Science," 1 (1996), 423-431). To carry out genetic engineering operations, nucleic acid molecules can be introduced into plasmids, and mutations or sequence changes can be generated by recombination of DNA sequences. Using the standard methods described above, for example, substrates can be exchanged, partial sequences can be removed, or natural or synthetic sequences can be added. To connect DNA fragments to one another, it is possible to attach binding partners or linkers to the fragments.

[0068] Plant cells in which the activity of a gene product is reduced can be prepared, for example, by expressing at least one appropriate antisense RNA, sense RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the gene product.

[0069] For this purpose, it is possible to use a DNA molecule that comprises the entire coding sequence of the gene product, including any flanking sequences that may be present, and to use a DNA molecule that comprises only a portion of the coding sequence, which portion must be long enough to achieve an antisense effect in the cell. Sequences that are highly homologous to the coding sequence of the gene product, but not identical thereto, can also be used.

[0070] When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired plant cell compartment. However, in order to localize in a specific compartment, it is possible, for example, to link the coding region to the DNA sequence to ensure localization at a specific position. These sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992) 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 65 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

[0071] Transgenic plant cells can be incorporated into whole plants using known techniques. Transgenic plants can be of any desired plant variety, i.e., monocotyledons and dicotyledons. In this way, it is possible to obtain transgenic plants with improved traits by overexpressing, inhibiting or suppressing homologous (=natural) genes or gene sequences, or by expressing heterologous (=foreign) genes or gene sequences.

[0072] When the active substances of the present invention are used on genetically modified crops, in addition to the harmful plant growth inhibitory effects observed on other crops, they often exhibit specific effects on the corresponding genetically modified crops, such as improved or expanded weed control, improved application rates, preferably a good combination of the resistance of the genetically modified crop and the performance of the herbicide, and effects on the growth and yield of the genetically modified crop plants. Therefore, the present invention also provides the use of the compounds as herbicides for controlling harmful plants in genetically modified crop plants.

[0073] Furthermore, the compounds of the present invention can significantly regulate the growth of crop plants. By modulating plant metabolism, these compounds can be used to control plant composition and promote harvest, for example by causing plant desiccation and dwarfing. Furthermore, they are suitable for regulating and inhibiting undesirable plant growth without disrupting crop growth. Inhibiting plant growth plays a very important role in many monocotyledonous and dicotyledonous crops because it can reduce or completely prevent lodging.

[0074] The compound of the present invention can be applied using general formulations, and wettable powders, emulsion concentrates, sprayable solutions, powders or granules can be used. Thus, the present invention also provides herbicidal compositions comprising compounds of formula I. According to common biological and / or chemical physical parameters, compounds of formula I can be formulated in a variety of ways. Suitable formulation selection examples are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsion concentrates (EC), emulsions such as oil-in-water dispersions and water-in-oil dispersions (EW), sprayable solutions, suspension concentrates (SC), dispersible oil suspensions (OD), suspensions with oil or water as diluents, solutions of miscible oils, powders (DP), capsule suspensions (CS), seeded compositions, granules for broadcasting and soil application, spray granules, coated granules and absorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV (ultra-low volume) formulations, microcapsules and wax products. These individual formulation types are known and are described, for example, in Winnacker-Küchler, "Chemische Techonologie" [Chemical Technology], Vol. 7, C. Hauser Verlag Munich, 4th edition 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973; K. Martens, "Spray Drying" Handbook, 3rd edition 1979, G. Goodwin Ltd. London.

[0075] Necessary formulation auxiliaries, such as inert substances, surfactants, solvents and other additives are likewise known and described in, for example, Watkins, "Handbook of Powder Diluents, Pesticides and Carriers," 2nd ed., Darland, Caldwell, NJ; Hvophen, "Introduction to Clay Colloid Chemistry," 2nd ed., J. Wiley and Sons, NY; C. Marsden, "Solvent Guide," 2nd ed., Interscience, NY 1963; McCutcheon, "Detergents and Emulsifiers Annual," MC Publishing Company, Ridgewood, NJ; Sisley and Wood, "Encyclopedia of Surfactants," Chemical Publishing Company, NY 1964; of [Ethylene oxide adduct surfactants], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Vol. 7, C. Hauser Verlag Munich, 4th edition 1986.

[0076] Wettable powders are homogeneously dispersible in water and contain, in addition to the active substance, a diluent or inert substance, ionic and nonionic surfactants (wetting agents, dispersants), for example, polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkylsulfonates, alkylphenylsulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthomethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. To prepare wettable powders, the herbicide active substance is finely ground, for example using conventional apparatus such as hammer mills, fan mills or jet mills, and the adjuvants are mixed in simultaneously or sequentially.

[0077] The concentrated emulsion is prepared by dissolving the active substance in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene or a mixture of relatively high-boiling aromatic compounds or hydrocarbons or solvents, and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.

[0078] Powders are obtained by grinding the active substance with finely divided solid materials, such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspensions in water or oil can be prepared, for example, by wet grinding using a commercially available bead mill, with or without the addition of a surfactant of the type described above for the other formulations.

[0079] Emulsions such as oil-in-water emulsions (EW) can be prepared using aqueous organic solvents using stirrers, colloid mills and / or static mixers and, if desired, adding surfactants of another formulation type as described above.

[0080] Granules can be prepared by spraying the active substance onto an adsorbent and granulating with an inert material, or by concentrating the active substance onto the surface of a carrier such as sand or kaolinite and granulating the inert material with a binder such as polyvinyl alcohol, sodium polyacrylate, or mineral oil. Suitable active substances can be granulated using methods for preparing fertilizer granules and, if desired, mixed with fertilizers. Aqueous suspension granules can be prepared using conventional methods, such as spray drying, fluidized bed granulation, disc granulation, mixing using a high-speed mixer, and extrusion in the absence of solid inert materials.

[0081] For the preparation of granules using a mill, fluidized bed, extruder, and spraying, see, for example, the following processes: "Spray Drying Handbook," 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, "Agglomeration," Chemistry and Engineering, 1967, pp. 147ff; "Perry's Chemical Engineer's Handbook," 5th ed., McGraw-Hill, New York, 1973, pp. 8-57. For the formulation of crop protection products, see, for example, G. C. Lingman, "Weed Control as a Science," John Wiley & Sons, New York, 1961, pp. 81-96 and J. D. Frieder, S. A. Evans, "Weed Control Handbook," 5th ed., Blackwell Scientific Research, Oxford, 1968, pp. 101-103.

[0082] Agrochemical formulations typically contain 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the active substance of Formula I. The active substance concentration in wettable powders is, for example, from about 10 to 99% by weight, with the formulation components typically comprising the remainder to 100% by weight. The active substance concentration in emulsifiable concentrates can range from about 1 to 90% by weight, preferably 5 to 80%. Powder formulations contain 1 to 30% by weight of active substance, typically preferably 5 to 20% by weight, while sprayable solutions contain approximately 0.05 to 80% by weight, preferably 2 to 50% by weight. The active substance content in water-suspendable granules depends primarily on whether the active substance is liquid or solid, and on the adjuvants, fillers, etc. used in granulation. The active substance content in water-suspendable granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

[0083] The active substance formulations may additionally include tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and, generally, pH and viscosity regulators which are customary in each case.

[0084] Based on these formulations, it is also possible to mix with other pesticide active substances such as insecticides, acaricides, herbicides and fungicides, as well as with safeners, fertilizers and / or plant growth regulators, either as premixes or as canned mixes.

[0085] In mixed formulations or tank-mixed formulations, suitable active substances that can be mixed with the active substance of the present invention are, for example, known substances described in "World New Pesticide Variety Technology Encyclopedia", China Agricultural Science and Technology Press, September 2010, and the literature cited therein. For example, the following herbicide active substances can be mixed with the mixture of formula I (Note: the name of the compound is either the common name according to the International Organization for Standardization (ISO) or the chemical name, with a code number when appropriate): acetochlor, butachlor, alachlor, isopropyl metolachlor, isopropyl metolachlor, S-isopropyl metolachlor, pretilachlor, acetochlor, acetochlor, naphthiachlor, R-(l-)naphthiachlor, propanil, mefenacet, bisbencarb, fluazifop, flufenacet, cyfluthrin, flumethalin, bromomethalin, dimethathiachlor, high-efficiency dimethathiachlor, ethoxymethalin, flufenacet, methoxymethalin, metazachlor, isopropyltrimonium chloride, high-efficiency cyfluthrin, Dipropylene glycol, pethoxachlor, butyrac, cyproconazole, flumethalin, heptamiprole, isobutachlor, propargyl chloramine, terbutachlor, dimethylaminopropylamine, dimethoate, chlorfenapyr, trimethylcyclohexane, chlorfenapyr, propyracyl chloramine, valeryl chloramine, carbamyl, new Yanling, tricyclic chlorfenapyr, butenesulfonamide, butenesulfonamide, mesotrione, benzylchlor, quinone, benzfluorosulfonamide, naphthamide, acetoacetamide, naphthamide, thiazolin, cypermethrin, benzylchlor, benzylchlor, cypermethrin, benzylchlor, cypermethrin, atrazine, simazine, promethazine, cyanamide, simethazine, ametryn, propazine, isopropylamine, fluroxypyr, terbutylamine, terbutylazine, triazine fluazifone, cyprodinil, gampopazine, thiophanate , Promethazine, Simatolin, Azide, Dichlorvos, Isopropylamine, Cyprodinil, Metazine, Another Butylazine, Second Butylazine, Terbutalone, Methoxypropylamine, Cyanamide, Cyanocyanine, Kolazone, Atrazine, Metazine, Glycyrrhizin, Cyanuric acid, Indaziflam, Chlorsulfuron, Metsulfuron-methyl, Bensulfuron-methyl, Chlorimuron-methyl, Bensulfuron-methyl, Thisulfuron-methyl, Pyrazosulfuron-methyl, Metsulfuron-methyl, Iodosulfuron-methyl sodium salt, Formamidosulfuron-methyl, Ethylsulfuron-methyl, Bensulfuron-methyl, Metsulfuron-methyl, Nicosulfuron, Ethamidosulfuron-methyl, Acesulfuron-methyl, Ethoxysulfuron-methyl, Cyprodinil, Sulfonsulfuron-methyl, Tetrazosulfuron, Fentazuron-methyl, Monosulfuron-methyl, Monosulfuron, Fluazuron-methyl, Flupyrazosulfuron-methyl, Epoxysulfuron Sulfur-methyl, azole pyrazosulfuron, primisulfuron, propensulfuron-methyl, trifloxysulfuron, sulfosulfuron, trifloxysulfuron, trifloxysulfuron, metsulfuron-methyl sodium, primisulfuron, methylthiosulfuron, pyrimidisulfon-methyl, Propyrisulfuron (propyrisulfuron), pyrazosulfuron-methyl, acifluorfen, fomesafen, lactofen, fluazifop-butyl, oxyfluorfen, oxazolidinone, benfibrate, chlorpyrifos ethyl, methylcarboxylic acid butyl, trifluoroacetic acid butyl, methoxy-nitropropane, trifluosuccinate, fluorinated herbicide ether, flutosulfuron, nitropropane, methylpyralid, dimethoate, flutosulfuron, flutosulfuron ester, Halosafen, chlorotoluron, isoproturon, linuron, diuron,Saproron, Fluorouron, Benthiocarb, Methylbenthiocarb, Benthiocarb, Sulfathiocarb, Isoxuron, Terbuthiuron, Clodinuron, Chlorbromon, Methylthiocarb, Acyril, Methoxythiocarb, Bromothiocarb, Methoxythiocarb, Chlorthiocarb, Monisouron, Cyclothiocarb, Fenuron, Flusulfuron, Cyclothiocarb, Cyclothiocarb, Cyclothiocarb, Cyclothiocarb, Thiofuron, Buthiuron, Cyclothiocarb, Parafluron, Methiathiazolin, Lomthiocarb, Trimethylisourea, Oxazol, Monisouron, Anisuron, Methiuron, Chloreturon, Tetrafluron, Betaine, Betaine-ethyl Ester, Betaine, Sulfathiocarb, Terbuthiuron, Avena Cinnamomum, Anipropyrin, Chlorprophion, Diclofenac, Anipropyrin, Chlorpheniramine, Carboxazo le, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbasulam, Butylcarb, Fenasulam ... 2-Methyl-4-chlorobutyric acid, 2,4,5-T, 2,4,5-T propionic acid, 2,4,5-T butyric acid, 2-Methyl-4-chloroamine salt, Mediben, Cypermethrin, Fenpyraclostrobin ... in, propanol, glyphosate, safflower, glufosinate, methylamine glufosinate, glufosinate sulfide, piperphosphine, bialaphos, disulfide, glufosinate, vine glufosinate, valoron, dimethylamino glufosinate, oxalophos, imazapyr, imazapyr, imazapyr, imazapyr, imazapyr ammonium, imazapyr, imazapyr, cloflupyr, cloflupyr 2-ethylhexyl ester, clopyralid, amiloride, triclopyr, dithiopyr, halofop, triclopyralid, thiopyralid, flupyralid, chlorpyrifos, flupyralid, chlorpyrifos, flupyralid, flupyralid, triclopyralid butoxyethyl ester, Cliodinate, sethoxydim, clethodim, cycloxydim, chlorpyrifos, cyclohexanone, butoxydim, oxaclofop, pyraclofop, Buthidazole, metribuzin,Hexazinone, Metamitron, Ethylmetribuzin, Ametridione, Amibuzin, Bromoxynil, Octanoyl Bromoxynil, Octanoyl Ioxyl, Ioxyl, Dichlobenil, Diphenylacetonitrile, Dipyridamole, Hydroxypyridamole, Iodobonil, Sulfursulfuron, Difluorosulfuron, Penoxsulam, Sulfursulfuron, Chlorosulfuron, Dichlorosulfuron, Pyroxypyramide, Fluorosulfuron, Bispyribac-butyl, Cyclopyramide, Pyroxypyramide, Pyroxypyramide, Bispyribac-butyl, Cyclopyramide, Pyroxypyramide, Bispyribac-butyl, Mesotrione, Sulcotrione, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, Isoxaflutole, Isoxachlorpyrifos, Fenoxasulfone, Me Thiozolin, isopropylpyraclostrobin, pyrasulfobutyl, pyrazoline, wild yanquat, benzylpyrazone, pyrasulfotole, pyroxasulfone, pyrasulfobutyl, fluazifop, chlorfenapyr, fenpyrazone, fluazifop, sulfentrazone, bencarbazone, fluazifop-butyl, bromocriptine, isothiocyanate, cypermethrin, cypermethrin, terclopyralid, flupropacil, flupropacil, flufenacet, fluazifop-butyl, clofosamide, phthalein, flumezin, pentachlorophenol (sodium), dinoseb, teroseb, terosebate, pentachlorophenol, dinitrophenol, chlorfenapyr, dinoseb, teroseb, oxadiazol, oxadiazol, cyclopentadiazol , fluazifop-butyl, fluazifop-butyl, tetrazolam, fluazifop-butyl, herbicide-resistant, bromomyxin, dimethylpyridasulfuron, pyridafol, chlorfenapyr, chlorfenapyr, chlorfenapyr, pyridafol, quinclorac, chlormequat, bentazon, pyridasulfuron, oxaziclomefop-butyl, chlorfenapyr, isopropylpyridasulfuron, chlorfenapyr, sodium chlorate, thatch Cetirizine, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, bromophenol oxime, triazole sulfonate, methomyl, furazolidone, furazolidone, ethylfuransulfonate, chloranil, chlorthalidone, fluazifop, barnyardgrass, acrolein, benzylpyridinium chloride, benzylpyridinium chloride, avena sativa ester, thiadiazole, cotton amine, hydroxythiocarb, methoxybenzone, benzylpyridinium chloride, chloranil, trichloropropionic acid, Alora c、Diethamquat、Etnipromid、Iprymidam、Ipfencarbazone、Thiencarbazone-methyl、Pyrimisulfan、Chlorflurazole、Tripropindan、Sulglycapin、Methylsulfuron、Cambendichlor、Cyclopropane、Thiocyananilide、Fenthiocarbazone、Fenthiocarbazone、Fenthiocarbazone-methyl、Pyrimisulfan、Chlorflurazole、Tripropindan、Sulglycapin、Methiosulfuron、Cambendichlor、Cyclopropane ...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. ,

[0086] When used, if necessary, commercially available formulations are diluted in a common manner, for example, in the case of wettable powders, concentrated emulsions, suspensions and granules suspended in water, with water dilution. Powders, granules used for soil application or solutions for broadcasting and spraying generally do not require further dilution with an inert substance before use. The required use amount of the compound of formula I varies with external conditions, such as temperature, humidity, the nature of the herbicide used, etc. It can have a large range of variation, for example between 0.001 and 1.0 kg ai / ha, or more active substance, but preferably between 0.005 and 750 g ai / ha, particularly between 0.005 and 250 g ai / ha. DETAILED DESCRIPTION

[0087] The following examples are used to illustrate the present invention and should not be regarded as limiting the present invention in any way. The scope of rights claimed for protection by the present invention is described by the claims. In view of the economy and diversity of the compounds, we preferably synthesized some compounds. Among the many compounds synthesized, some are selected and 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 illustrating the present invention, but do not limit the present invention. For those skilled in the art, this should not be understood as the scope of the above-mentioned subject matter of the present invention being limited to the following compounds.

[0088] Table 1 Compound structures and their 1 H NMR values

[0089] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The starting materials can be purchased commercially or can be prepared by methods known in the literature or as described in detail. It will be understood by those skilled in the art that other synthetic routes can also be used to synthesize the compounds of the present invention. Although the specific starting materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar starting materials and conditions, and these modifications or variations of the preparation methods of the present invention that result in various isomerizations of the compounds are included within the scope of the present invention. In addition, the preparation methods described below can be further modified according to the present disclosure using conventional chemical methods well known to those skilled in the art. For example, appropriate groups can be protected during the reaction, etc.

[0090] The following process examples are provided to facilitate a further understanding of the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further illustrate the present invention and are not intended to limit its reasonable scope. The reagents used in the synthesis of the compounds shown in the table below are either commercially available or can be readily prepared by one of ordinary skill in the art.

[0091] Examples of representative compounds are shown below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0092] 1. Synthesis of Compound 1

[0093] (1) 1-1 (500 mg, 1.00 eq) was dissolved in THF (10.0 mL), replaced with nitrogen three times, and cooled to -70°C using dry ice / EA. LDA (2.00 M, 1.34 mL, 1.50 eq) was added and the temperature was maintained for 0.5 h. DMF (196 mg, 1.50 eq) was added and the temperature was maintained for 0.5 h. The reaction solution was quenched by adding dilute aqueous hydrochloric acid and diluted with acetonitrile. LCMS was used to monitor the disappearance of the starting material, and the product was the main peak. The reaction solution was returned to room temperature, and dilute aqueous hydrochloric acid and ethyl acetate were added. The layers were separated, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed once with saturated brine, and silica gel was added to mix the sample. The normal phase separation gave 1-2 (400 mg, yield = 73%).

[0094] (2) 1-3 (310 mg, 1.40 eq) was dissolved in toluene (7.00 mL), replaced with nitrogen three times, and cooled to -70°C using dry ice / EA. n-Butyl lithium (2.5 M, 0.44 mL, 1.20 eq) was added, and the temperature was maintained for 15 minutes. 1-2 (285 mg, 1.00 eq) was added to the system, and the temperature was maintained for 45 minutes. The reaction solution was quenched by adding dilute aqueous hydrochloric acid and diluted with acetonitrile. LCMS was used to monitor the disappearance of the starting material, and the product was the main peak. The reaction solution was returned to room temperature, and dilute aqueous hydrochloric acid and ethyl acetate were added. The layers were separated, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed once with saturated brine, and silica gel was added to the sample. The normal phase separation gave 1 (100 mg, yield = 25%) as a light yellow solid.

[0095] 2. Synthesis of Compound 17

[0096] Compound 1 (200 mg, 1.0 eq) was dissolved in 5 mL of DCM. Acetic anhydride (97 mg, 2 eq) and triethylamine (144 mg, 3.0 eq) were added at 0°C and stirred overnight at room temperature. LCMS monitored the reaction for completion. The reaction solution was diluted with ethyl acetate, and the organic phase was washed with saturated brine, dried, and concentrated. The residue was purified by column chromatography to afford compound 17 (100 mg, 45%).

[0097] 3. Synthesis of Compound 95

[0098] (1) LDA (11 mL, 2 M solution in tetrahydrofuran) was added to 20 mL of THF at 0°C, followed by compound 95-1 (1 g, 1.0 eq). After reacting for 1 h, the temperature was lowered to -78°C, and ethyl difluoromethylate (1.5 g, 1.3 eq) was added dropwise. The temperature was slowly raised to room temperature and allowed to react overnight. LCMS was used to monitor the reaction until completion. Dilute hydrochloric acid was added dropwise to quench the reaction, and the organic phase was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried, and concentrated to give crude product 95-2 (4 g).

[0099] (2) Compound 95-2 (800 mg, 1.0 eq) was dissolved in 20 mL of glacial acetic acid, and compound 95-3 (1 g, 1.0 eq) was added at room temperature. The mixture was stirred at room temperature for 2 hours. LCMS confirmed the completion of the reaction. The mixture was diluted with ethyl acetate, and the organic phase was washed with saturated brine, dried, and concentrated. The residue was purified by column chromatography to afford compound 95-4 (600 mg, 36%).

[0100] (3) Compound 95-4 (600 mg, 1.0 eq) was dissolved in 20 mL of dimethyl sulfoxide, and 2,5-dichloropyrimidine (1.23 g, 5 eq) and sodium tert-butoxide (1.11 g, 7 eq) were added. The mixture was stirred at 40°C for 2 h and monitored by LCMS until the reaction was complete. The mixture was quenched with water and extracted with ethyl acetate. The organic phase was washed with saturated brine, dried, and concentrated. The residue was purified by column chromatography to obtain compound 95 (110 mg, 14%).

[0101] 4. Synthesis of Compound 75

[0102] (1) The raw material 75-1 (5.0 g, 1.0 eq) was dissolved in THF under nitrogen protection. LDA (1.5 eq) was added dropwise at -78°C and stirred for 30 minutes. DMF was then added and stirred at the same temperature for 2 hours. After the reaction was completed by LCMS monitoring (quenched with dilute hydrochloric acid), dilute hydrochloric acid was added to quench the reaction, extracted with EA, dried, and purified by normal phase purification to obtain the product 75-2 (3.0 g, 55% yield).

[0103] (2) Raw material 1-3 (1.2 eq) was dissolved in toluene under nitrogen protection. n-Butyl lithium was added dropwise at -78°C and stirred for 30 minutes. Raw material 75-2 (2.0 g, 1.0 eq) was then added and stirred at the same temperature for 2 hours. After the reaction was completed by LCMS monitoring (quenched with dilute hydrochloric acid), dilute hydrochloric acid was added to quench the reaction, extracted with EA, dried, and purified by normal phase purification to obtain product 75 (1.5 g, 58% yield).

[0104] 5. Synthesis of Compound 101

[0105] Compound 98 (200 mg, 1.00 eq) was dissolved in isopropanol (5 mL), and 3 drops of tetraisopropyl titanate were added dropwise. The mixture was stirred at 80°C for 10 hours. LCMS confirmed the reaction was complete. The reaction solution was cooled to room temperature and diluted with ethyl acetate. The organic phase was washed with saturated brine, dried, and concentrated. The residue was purified by column chromatography to afford Compound 101 (150 mg, 72%) as a white solid.

[0106] 6. Synthesis of Compound 108

[0107] Compound 1 (100 mg, 1.0 eq) was dissolved in 5 mL of DCM, and DAST (76 mg, 1.0 eq) was added dropwise at 0°C. The mixture was stirred overnight at room temperature. Upon completion of the reaction, ice water was added to quench the reaction. The mixture was extracted with DCM, and the organic phase was washed with saturated brine, dried, and concentrated. The residue was purified by column chromatography to afford 108 (50 mg, 46%) as a light yellow oil.

[0108] 7. Synthesis of Compound 112

[0109] (1) Dissolve raw material 1-3 in toluene under nitrogen protection, add n-butyl lithium dropwise at -78°C, and stir for 30 minutes. Then add raw material 112-1 and maintain the temperature and stir for 2 hours. After the reaction is completed by LCMS monitoring (quenching with dilute hydrochloric acid), quench the reaction with dilute hydrochloric acid, extract with EA, dry, and then purify with normal phase to obtain product 112-2.

[0110] (2) Dissolve the raw material 112-2 in DCM, add DAST, and stir at room temperature overnight. After the reaction is completed as monitored by LCMS, the solvent is dried and the product 112 is obtained by normal phase purification.

[0111] 8. Synthesis of Compound 134

[0112] (1) Compound 134-1 (8.0 g, 1.0 eq) was dissolved in a solvent (MeCN: 100 mL), and Cu(OAc)2 (9.69 g, 1.0 eq), compound 134-2 (9.6 g, 1.2 eq), and 4A molecular sieves (3.0 g) were added. The mixture was then reacted at 50°C under an oxygen atmosphere for 12 h. LCMS monitored the reaction to be complete, with the main peak of the product. The silica gel sample was flash purified (0-25% EA / PE) to afford compound 134-3 (12.0 g, 89.2%).

[0113] (2) Compound 134-3 (12 g, 1.0 eq) was dissolved in a solvent (DCM: 120 mL) and DAST (38.07 g, 5.0 eq) was added dropwise at 0°C. The mixture was then stirred at room temperature overnight. LCMS monitored the reaction to be complete, with the product as the main peak. The product was quenched with ice water after post-treatment, and the organic phase was dried and concentrated. The residue was flash purified (0-25% EA / PE) to afford compound 134-4 (9.22 g, 85.4%).

[0114] (3) Compound 134-4 (9.22 g, 1.0 eq) was dissolved in a solvent (CCl4: 100 mL), and AIBN (5.66 g, 1.0 eq) was added, followed by NBS (7.13 g, 1.2 eq). The mixture was stirred under reflux overnight. LCMS monitored the reaction to be complete, with the main peak of the product. The product was quenched with ice water, extracted with DCM, and the organic phase was dried and concentrated. The residue was flash purified (0-25% EA / PE) to afford compound 134-5 (11.0 g, 94%).

[0115] (4) Compound 134-5 (11.0 g, 1.0 eq) was dissolved in a solvent (MeCN: 110 mL), and NMO (5.45 g, 1.5 eq) was added. The mixture was stirred under reflux overnight. LCMS monitoring indicated that the reaction was complete and the product was the main peak. The reaction solution was concentrated and extracted with EA / water. The organic phase was dried and concentrated. The residue was flash purified (0-25% EA / PE) to afford compound 134-6 (4.2 g, 43.7%).

[0116] (5) Compound 1-3 (6.95 g, 2.0 eq) was dissolved in a solvent (THF: 110 mL) under nitrogen protection. n-Butyl lithium (8.7 mL, 1.5 eq) was added dropwise at -78°C, followed by stirring for 2 h. Compound 134-6 (4.2 g, 1.0 eq) was then added and stirred at room temperature for 1 h. LCMS monitoring indicated that the reaction was complete and the product was the main peak. The product was quenched with ice water, extracted with EA, and the organic phase was dried and concentrated. The residue was flash purified (0-25% EA / PE) to give compound 134-7 (3.2 g, 50%).

[0117] (6) Compound 134-7 (200 mg, 1.0 eq) was dissolved in a solvent (DCM: 2 mL) and DAST (399 mg, 5.0 eq) was added dropwise at 0°C. The mixture was then stirred at room temperature for 2 h. LCMS analysis revealed the reaction was complete and the product was the main peak. The product was quenched with ice water and the organic phase was dried and concentrated. The residue was flash purified (0-25% EA / PE) to afford compound 134 (150 mg, 75%).

[0118] 9. Synthesis of Compound 143

[0119] (1) Dissolve the starting material 143-1 in toluene, add the starting material 143-2, CuI, potassium carbonate, and 1,2-cyclohexanediamine ligand, and stir at 110°C overnight under nitrogen protection. After completion of the reaction, monitor by LCMS, dry the product and purify it with normal phase chromatography to obtain the product 143-3.

[0120] (2) The raw material 143-3 was dissolved in THF under nitrogen protection. LDA was added dropwise at -78°C and stirred for 30 minutes. DMF was then added and stirred at the same temperature for 2 hours. After the reaction was completed by LCMS monitoring (quenched with dilute hydrochloric acid), the reaction was quenched with dilute hydrochloric acid, extracted with EA, dried, and purified by normal phase purification to obtain the product 143-4.

[0121] (3) Raw material 1-3 was dissolved in toluene under nitrogen protection. n-Butyl lithium was added dropwise at -78°C and stirred for 30 minutes. Raw material 143-4 was then added and stirred at the same temperature for 2 hours. After completion of the reaction (quenched with dilute hydrochloric acid), dilute hydrochloric acid was added to quench the reaction, extracted with EA, and dried, followed by normal phase purification to obtain product 70.

[0122] (4) The starting material 70 was dissolved in DCM, DAST was added, and the mixture was stirred at room temperature overnight. After completion of the reaction monitored by LCMS, the solvent was dried, and the product 143 was obtained by normal phase purification.

[0123] 10. Synthesis of Compound 145

[0124] The starting material 75 (170 mg, 1.0 eq) was dissolved in DCM solution, DAST (3.0 eq) was added, and the mixture was stirred at room temperature overnight. After the reaction was completed as monitored by LCMS, the solvent was dried and the product 145 (150 mg, yield 88%) was obtained by normal phase purification.

[0125] 11. Synthesis of Compound 154

[0126] The starting material 112-2 was dissolved in DCM solution, SOCl2 was added, and stirred at room temperature overnight. After the reaction was completed by LCMS monitoring, the solvent was dried and the product 154 was obtained by normal phase purification.

[0127] 12. Synthesis of Compound 203

[0128] The starting material 75 was dissolved in DCM solution, SOCl2 was added, and stirred at room temperature overnight. After the reaction was completed by LCMS monitoring, the solvent was dried and the product 203 was obtained by normal phase purification.

[0129] 13. Synthesis of Compound 210

[0130] At 0°C, compound 210-1 (100 mg, 0.25 mmol) was dissolved in carbon tetrachloride (5 mL), and NBS (54 mg, 0.3 mmol) and AIBN (4 mg, 0.025 mmol) were added sequentially. After the addition was complete, the mixture was refluxed with stirring overnight. After the reaction was completed, water was added and the mixture was extracted three times with DCM. The combined organic phases were washed with saturated brine and dried over anhydrous sodium sulfate. The organic phase was spin-dried and purified by normal phase to obtain 210 (white solid, 97 mg, yield 80%).

[0131] 14. Synthesis of Compound 238

[0132] (1) Compound 238-1 (1.1 g, 4.84 mmol) was dissolved in 10 mL of concentrated hydrochloric acid solution at 0°C, and then an aqueous sodium nitrite solution (0.5 g, 7.26 mmol) was added. After the addition, the reaction solution was stirred at 0°C for 0.5 h. Subsequently, stannous chloride (2.3 g, 12.1 mmol) was dissolved in concentrated hydrochloric acid solution and slowly added dropwise to the reaction solution. The reaction solution was stirred at 0°C for 3 h and monitored by LCMS until the reaction was complete. Water was added to the reaction solution to quench the reaction, and the solution was extracted three times with saturated sodium bicarbonate solution and ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and then concentrated to obtain crude compound 238-2 (1.0 g, 85%, yellow crude product).

[0133] (2) Compound 238-2 (1.0 g, 4.13 mmol) was dissolved in 10 mL of glacial acetic acid. Compound 238-3 (0.93 g, 4.13 mmol) was added at room temperature. After addition, the mixture was stirred at room temperature for 2 h. The reaction was monitored by LCMS until completion. The reaction solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate, concentrated, and purified by normal phase purification (PE / EA = 8 / 1) to afford compound 238-4 (0.8 g, 45%, yellow solid).

[0134] (3) Compound 238-4 (0.8 g, 1.85 mmol) was dissolved in 10 mL of dimethyl sulfoxide solution, followed by the addition of 2,5-dichloropyrimidine (0.33 g, 2.22 mmol) and sodium tert-butoxide (1.24 g, 12.95 mmol). After the addition, the reaction solution was stirred at 40°C overnight and monitored by LCMS until the reaction was complete. The reaction solution was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The reaction solution was then concentrated and mixed, and purified by normal phase purification (PE / EA = 5 / 1) to obtain compound 238 (0.65 g, 64%, yellow oil).

[0135] 15. Synthesis of Compound 247

[0136] Raw materials 247-1 (1.0 g, 2.7 mmol) and 247-2 (2.50 g, 2.19 mmol) were dissolved in 20 mL of DMSO, and t-BuONa (1.8 g, 18.9 mmol) was added and allowed to react at room temperature for 3 h. After the intermediate reaction, water and EA were added. The EA phase was washed with water and saturated brine, dried, and purified by normal phase purification to afford 247 (152 mg, 12%).

[0137] Biological activity evaluation:

[0138] The activity level standards for plant damage (i.e., growth control rate) are as follows:

[0139] Level 9: Complete death;

[0140] Level 8: Growth control rate is greater than or equal to 90% and less than 100%;

[0141] Level 7: Growth control rate is greater than or equal to 80% and less than 90%;

[0142] Level 6: Growth control rate is greater than or equal to 70% and less than 80%;

[0143] Level 5: Growth control rate is greater than or equal to 50% and less than 70%;

[0144] Level 4: Growth control rate is greater than or equal to 30% and less than 50%;

[0145] Level 3: Growth control rate is greater than or equal to 20% and less than 30%;

[0146] Level 2: Growth control rate is greater than or equal to 10% and less than 20%;

[0147] Level 1: Growth control rate is less than 10%;

[0148] Level 0: No effect.

[0149] The above growth control rates are fresh weight control rates.

[0150] Post-emergence test:

[0151] Monocotyledonous and dicotyledonous weed seeds, as well as staple crop seeds, were placed in plastic pots filled with soil, covered with 0.5-2 cm of soil, and grown in a well-maintained greenhouse environment. Two weeks after sowing, at the 2-3 leaf stage, test plants were treated. The test compounds of the present invention were dissolved in acetone, Tween 80 was added, and 1.5 L / hectare of methyl oleate emulsifiable concentrate was used as a synergist. The solution was diluted with water to a desired concentration and sprayed onto the plants using a spray tower. Following incubation in the greenhouse for three weeks, the weed response was assessed. Representative data are listed in Table 2.

[0152] Table 2 Post-emergence test results

[0153] Note: N stands for no data, reference compound A: Control compound B:

[0154] Pre-emergence testing:

[0155] Monocotyledonous and dicotyledonous weed seeds, as well as staple crop seeds, were placed in plastic pots filled with soil and covered with 0.5-2 cm of soil. The test compounds of the present invention were dissolved in acetone, then diluted with Tween 80 and water to a desired concentration. The solutions were sprayed immediately after sowing. The plants were incubated in a greenhouse for three weeks after application and observed for test results. Representative data are listed in Table 3.

[0156] Table 3 Pre-emergence test results

[0157] Note: N stands for no data.

[0158] At the same time, many tests have found that the compounds and compositions of the present invention can control many key grass weeds, broadleaf weeds and sedges, etc., showing excellent commercial value.

[0159] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not limiting. Although the present invention has been described in detail with reference to the preferred embodiments, those skilled in the art should understand that the technical solutions of the present invention may be modified or replaced by equivalents without departing from the spirit and scope of the technical solutions of the present invention.

Claims

1. A pyrazole pyrimidine compound or a salt thereof as represented by the general formula I: in, X represents halogen, -OX1, -(CO)OX2, -(CO)SX2 or -(CO)N(X2)2; X1 represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, -(CO)R9, -(CO)N(R9)2, -(CO)N(R9)(OR9) or -(CO)OR9, wherein the alkyl, alkenyl or alkynyl group is optionally selected from halogen, cycloalkyl, aryl, heterocyclyl, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2; X2 independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclic group, wherein the alkyl, alkenyl or alkynyl group is optionally selected from halogen, cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2; Y, Z, R1, R2, R3, R4, R5, R6, R7, and R8 independently represent hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclic, -OR9, -(CO)R9, -(CO)OR9, -(CO)N(R9)2, -CR9=N-OR9, -S(O) n R9 or -N(R9)2, the alkyl, alkenyl or alkynyl group is optionally selected from halogen, cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)OR9, -S(O) n R9 or -N(R9)2 is substituted by at least one group, or Y and Z together form -CH=CH-CH=CH-, or R6 and R7 together form -OCH2O- which is unsubstituted or substituted by halogen; n is 0, 1, or 2; R9 each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, wherein the alkyl, alkenyl or alkynyl group is optionally substituted by at least one group selected from halogen or alkoxy; The aforementioned "cycloalkyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR 10 、-SR 10 、-(CO)R 10 、-(CO)OR 10 、-(CO)N(R 10 )2、-(CS)N(R 10 )2、-(SO)R 10 or -(SO2)R 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure; R 10 Each of them is independently hydrogen, alkyl, haloalkyl, aryl or heterocyclic group which is unsubstituted or substituted by at least one group selected from halogen and alkyl.

2. The pyrazole pyrimidine compound according to claim 1, characterized in that X1 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, aryl, heterocyclyl, -(CO)R9, -(CO)N(R9)2, -(CO)N(R9)(OR9) or -(CO)OR9, wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally selected from halogen, C3-C8 cycloalkyl, aryl, heterocyclyl, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2; X2 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, aryl or heterocyclic group, wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally selected from halogen, C3-C8 cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2; Y, Z, R1, R2, R3, R4, R5, R6, R7, and R8 independently represent hydrogen, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)R9, -(CO)OR9, -(CO)N(R9)2, -CR9=N-OR9, -S(O) n R9 or -N(R9)2, the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally selected from halogen, C3-C8 cycloalkyl, aryl, heterocyclyl, -OR9, -(CO)OR9, -S(O) n R9 or -N(R9)2 is substituted by at least one group, or Y and Z together form -CH=CH-CH=CH-, or R6 and R7 together form -OCH2O- which is unsubstituted or substituted by halogen; R9 each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, aryl, arylC1-C8 alkyl, heterocyclyl or heterocyclylC1-C8 alkyl, wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally substituted by at least one group selected from halogen or C1-C8 alkoxy; The aforementioned "C3-C8 cycloalkyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, -OR 10 、-SR 10 、-(CO)R 10 、-(CO)OR 10 、-(CO)N(R 10 )2、-(CS)N(R 10 )2、-(SO)R 10 or -(SO2)R 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure; R 10 Each is independently hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, aryl or heterocyclic group which is unsubstituted or substituted with at least one group selected from halogen and C1-C8 alkyl.

3. The pyrazole pyrimidine compound according to claim 1, characterized in that X1 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, aryl, heterocyclyl, -(CO)R9, -(CO)N(R9)2, -(CO)N(R9)(OR9) or -(CO)OR9, wherein the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally selected from halogen, C3-C6 cycloalkyl, aryl, heterocyclyl, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2; X2 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, aryl or heterocyclic group, and the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally selected from halogen, C3-C6 cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)OR9, -S(O) n is substituted by at least one group in R9 or -N(R9)2; Y, Z, R1, R2, R3, R4, R5, R6, R7, and R8 independently represent hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)R9, -(CO)OR9, -(CO)N(R9)2, -CR9=N-OR9, -S(O) n R9 or -N(R9)2, the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally selected from halogen, C3-C6 cycloalkyl, aryl, heterocyclic group, -OR9, -(CO)OR9, -S(O) n R9 or -N(R9)2 is substituted by at least one group, or Y and Z together form -CH=CH-CH=CH-, or R6 and R7 together form -OCH2O- which is unsubstituted or substituted by halogen; R9 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, aryl, arylC1-C6 alkyl, heterocyclyl or heterocyclylC1-C6 alkyl, wherein the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally substituted by at least one group selected from halogen or C1-C6 alkoxy; The aforementioned "C3-C6 cycloalkyl", "heterocyclyl" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, -OR 10 、-SR 10 、-(CO)R 10 、-(CO)OR 10 、-(CO)N(R 10 )2、-(CS)N(R 10 )2、-(SO)R 10 or -(SO2)R 10 or two adjacent carbon atoms on the ring form a condensed ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure; R 10 are independently hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, aryl or heterocyclic group which is unsubstituted or substituted by at least one group selected from halogen and C1-C6 alkyl; Preferably, the compound is selected from any one of Table 1 in the specification.

4. The method for preparing the pyrazole pyrimidine compound according to any one of claims 1 to 3, comprising the following steps: When X represents -(CO)OX2, -(CO)SX2 or -(CO)N(X2)2, the compound represented by the general formula II is reacted with the compound represented by the general formula III to obtain the compound represented by the general formula I, and the reaction equation is as follows: When X represents halogen or -OX1, the compound shown in formula IV React with the compound shown in formula III to obtain the compound shown in formula I' Then the target compound is obtained through conventional substitution reaction; Alternatively, when X represents a halogen, Prepared by halogenation reaction; Wherein, L represents halogen, and the substituents X, R1, R2, R3, R4, R5, R6, R7, R8, Y and Z are defined as described in any one of claims 1 to 3; Preferably, the reaction for preparing the compound of formula I or I' is carried out in the presence of a base and a solvent; more preferably, the base is selected from at least one of an inorganic base or an organic base, and / or the solvent is selected from at least one of toluene, dichloroethane, dimethyl sulfoxide, acetonitrile, ethyl acetate, diethyl ether, hexane or tetrahydrofuran; Preferably, the halogenation reaction is carried out in the presence of a solvent, a halogenating agent and an initiator; more preferably, the solvent is selected from at least one of carbon tetrachloride, acetonitrile, dichloromethane, trifluorotoluene or benzene, the halogenating agent is selected from at least one of NBS, NCS, Br2, chlorine, I2 or thionyl chloride, and / or the initiator is selected from at least one of AIBN, benzoyl peroxide, DTBP or photoinitiator.

5. A herbicidal composition, characterized in that The invention comprises a herbicidally effective amount of at least one of the pyrazolopyrimidine compounds according to any one of claims 1 to 3; preferably, further comprises a formulation adjuvant; more preferably, further comprises other active ingredients.

6. A method for controlling weeds, comprising applying a herbicidally effective amount of at least one of the pyrazolopyrimidine compounds according to any one of claims 1 to 3 or the herbicide composition according to claim 5 to plants or weedy areas.

7. Use of the pyrazolopyrimidine compound according to any one of claims 1 to 3 or the composition according to claim 5 for controlling weeds. Preferably, the pyrazolopyrimidine compound is used to control weeds in useful crops, which are transgenic crops or crops treated with genome editing technology.

8. An intermediate, as shown in formula II or IV of claim 4.

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