A novel preparation method and application of thioamide compounds

Abstract

The present invention provides a preparation method and application of a novel thioamide compound, wherein the compound comprises a compound as shown in the general formula (I) and a salt of the compound as shown in the general formula (I); the compound or herbicidal composition of the embodiment of the present invention has a broad-spectrum herbicidal activity, and has a good control effect on barnyard grass, foxtail grass, crabgrass and Amaranthus retroflexus, etc., and can be used in wheat, soybeans, rice, corn, orchards and non-cultivated land to prevent and control various malignant weeds. R1 is selected from halogenated C1-C3 alkyl; R2 and R3 are selected from O and S respectively; and R2 and R3 are not selected from O at the same time, and at least one is selected from S; R4 is selected from methyl or ethyl.

Description

Technical Field

[0001] The present invention relates to the technical field of agricultural herbicides, and in particular to a preparation method and application of a novel thioamide compound. Background Art

[0002] Weed control is a crucial link in achieving efficient agriculture. Although there are various types of herbicides on the market, for example, WO2022238178A1, WO222238247A1, WO2020079078A1 and other invention embodiments describe certain aromatic formamide compounds and their use as herbicides. Due to years of long-term use, the problem of weed resistance has become increasingly prominent, especially with the serious occurrence of resistance to mainstream weed herbicides such as penoxsulam, bispyribac-butyl, cyhalofop-butyl, oxadiazine, and glyphosate, crops such as wheat and rice have encountered severe challenges and lack of effective agents for preventing and controlling resistant weeds. This requires scientists to continuously research and develop new varieties of herbicides that are efficient, safe, economical and have different modes of action.

[0003] Based on this, the present invention provides a novel thioamide compound and composition, their uses and methods of use. The compound and its composition have excellent herbicidal activity and higher crop safety, especially establishing good selectivity for key crops such as rice.

[0004] In view of this, the present invention is proposed. Summary of the invention

[0005] In order to meet the requirements in agriculture, the present invention provides a novel thioamide compound and a method for using the same for controlling weeds and the application of components containing the compounds in agriculture.

[0006] The present invention is achieved in that:

[0007] The present invention provides a novel thioamide compound or an agriculturally acceptable salt thereof, as shown in the general formula (I):

[0008]

[0009] Where:

[0010] R1 is selected from halogenated C1-C3 alkyl;

[0011] R2 and R3 are selected from O and S respectively; R2 and R3 are not selected from O at the same time, and at least one of them is selected from S; R4 is selected from methyl or ethyl;

[0012] Optionally, in the general formula (I):

[0013] R1 is selected from halogenated trifluoromethane and difluoromethane;

[0014] R2 and R3 are selected from O and S respectively; R2 and R3 are not selected from O at the same time, and at least one of them is selected from S; R4 is selected from methyl or ethyl;

[0015] Optionally, in the general formula (I), preferably selected from the following structures:

[0016]

[0017]

[0018] Optionally, the salt of the compound represented by general formula (I) is selected from one of the sodium salt, potassium salt, calcium salt and lithium salt of the compound represented by general formula (I), preferably one of the sodium salt, potassium salt and lithium salt.

[0019] In the definition of compounds of general formula (I) given above, the terms used collectively are generally defined as follows:

[0020] Unsubstituted means that all substituents are hydrogen.

[0021] Halogen: refers to fluorine, chlorine, bromine or iodine.

[0022] Haloalkyl: a linear or branched haloalkyl group, in which hydrogen atoms may be partially or completely substituted by halogen atoms, for example, a haloalkyl group such as chloromethyl, dichloromethyl, trichloromethyl, monofluoromethyl, difluoromethyl or trifluoromethyl.

[0023] A salt of a novel thioamide compound represented by the following general formula (II) and an acid or base addition:

[0024]

[0025] Wherein, R1, R2, R3, and R4 have the same meanings as defined in the general formula (I).

[0026] Acids that can form salts with the novel thioamide compounds represented by general formula (II) of the present invention include carboxylic acids, such as acetic acid, propionic acid, butyric acid, oxalic acid, trifluoroacetic acid; sulfonic acids, such as methanesulfonic acid, p-toluenesulfonic acid or dodecylbenzenesulfonic acid; and inorganic acids, such as hydrochloric acid, sulfuric acid, nitric acid or carbonic acid.

[0027] The bases and metals that can form salts with the novel thioamide compounds represented by the general formula (II) of the present invention include metals such as sodium, alkali, calcium, magnesium, etc.; organic bases such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium methoxide, potassium ethoxide, sodium formate, butyl lithium, sodium acetate, etc.; inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium hydroxide, lithium carbonate, sodium hydride, sodium amide, etc.;

[0028] Unless otherwise stated, the intermediates used in this article were purchased from the market.

[0029] The embodiments of the present invention also relate to the use of the compound or the herbicidal composition in weed control.

[0030] Compounds shown in the general formula (I) and agriculturally acceptable salts thereof are suitable for use as herbicides in the form of isomer mixtures and pure isomers. They are suitable for direct use or for use with appropriately formulated compositions. Herbicidal compositions comprising compounds shown in the general formula (I) are very effective in preventing and controlling plant growth in non-crop areas, especially at high application rates. They act on broadleaf weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to crops. This effect is mainly observed at low application rates.

[0031] In some embodiments, the compound represented by the general formula (I) and / or its salts of the embodiments of the present invention are suitable for controlling a wide range of harmful plants, such as the following monocotyledonous and dicotyledonous harmful plants, which are only used to illustrate the embodiments of the present invention, but are by no means limited to the embodiments of the present invention.

[0032] Monocotyledonous harmful plants of the following genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, El eusine), Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum.

[0033] Dicotyledonous harmful plants of the following genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurium urea), Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Phytophthora arbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0034] In some embodiments, when the compound of the present invention is applied to the soil surface before the harmful plants (gramineous weeds and / or broadleaf weeds) sprout (pre-emergence method), the seedlings of gramineous weeds and broadleaf weeds can be completely prevented from emerging from the soil, or they can be grown to the cotyledon stage and then stop growing, and finally die completely after three to four weeks.

[0035] In some embodiments, if the active compound is applied to the green parts of the plants after emergence, growth is stopped after the treatment and the harmful plants remain in the growth phase at the time of application or die completely after a certain period of time, thus eliminating the competition of weeds that are harmful to crop plants at a very early point in time and continuously.

[0036] Although the compounds of the embodiments of the present invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they only cause damage to crop plants of economically important crops to a small extent, or no damage at all, depending on the structure of each compound of the embodiments of the present invention and its application rate. The crop plants of the economically important crops are dicotyledonous crops such as those of the following genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotina, The present invention relates to a compound of the invention which is preferably a plant of the genus Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, and Zea. These examples are intended to illustrate, but are not intended to limit, the present invention. Thus, in some embodiments, the compounds of the present invention are well suited for selectively controlling unwanted plant growth in crop plants such as agriculturally useful plants or ornamental plants.

[0037] In addition, in some embodiments, the compounds of the embodiments of the present invention (depending on their specific structure and the application rate used) have excellent growth regulating properties for crop plants. They participate in the metabolism of the plant itself with a regulatory effect, and can be used to control plant components and promote harvesting, for example by inducing dehydration and dwarfing growth. In addition, they are also suitable for general prevention and control and inhibition of unwanted vegetative growth without damaging the plant in the process. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, because, for example, it can reduce or completely prevent lodging.

[0038] In some embodiments, due to the herbicidal and plant growth regulating properties of the active compound, it can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the characteristics of transgenic plants are particularly advantageous properties, such as resistance to certain pesticides: particularly certain herbicides, resistance to plant diseases or plant disease pathogens-such as certain insects or microorganisms (such as fungi, bacteria or viruses). Other specific properties relate to, for example, the quantity, quality, storage, composition and specific ingredients of the harvested material. For example, transgenic plants with increased starch content or improved starch quality, or transgenic plants whose harvested materials contain different fatty acid compositions are known. Other specific properties can be tolerance or resistance to abiotic stress factors, such as heat, cold, drought, salinity and ultraviolet radiation.

[0039] Contemplating transgenic plants, the compounds of the present invention of formula (I) and / or their salts are optionally used in economically important transgenic crops of useful plants and ornamental plants, such as cereals (e.g., wheat, barley, rye, oats, triticale, millet, rice, cassava and corn), or other crops such as sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.

[0040] Alternatively, the compounds of formula (I) are employed as herbicides in crops of useful plants which are resistant to the phytotoxic effects of herbicides or which have acquired such resistance by recombinant technology.

[0041] Conventional methods for producing novel plants with modified characteristics compared to existing plants comprise, for example, conventional breeding methods and the generation of mutants. Alternatively, novel plants with altered characteristics can be generated with the aid of recombinant methods.

[0042] Alternatively, the compound (I) of the embodiments of the present invention is used in transgenic crops resistant to the following substances: growth regulators, such as dicamba; or herbicides that inhibit plant essential enzymes, such as acetolactate synthase (ALS), EPSP synthase, glutamine synthetase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD); or herbicides selected from sulfonylureas, glyphosate, glufosinate or benzoyl isoxazole and similar active compounds.

[0043] When the active compounds of the embodiments of the present invention are used in transgenic crops, not only the effects on harmful plants observed in other crops appear, but also specific effects for application to specific transgenic crops often appear, such as an altered or particularly broadened range of weeds that can be controlled, an improved application rate that can be used for application, an optional good ability to combine with herbicides to which the transgenic crops are resistant, and an effect on the growth and yield of transgenic crop plants.

[0044] Therefore, embodiments of the present invention also relate to the use of the compounds of formula (I) and / or salts thereof according to embodiments of the present invention as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally transgenic crop plants.

[0045] In some embodiments, the present invention also relates to the use of the compound of formula (I) and / or its salt in cereals, such as soybean, corn, wheat, barley, rye, oats, millet or rice, by pre-emergence or post-emergence methods.

[0046] In one or more exemplary embodiments, the use of the embodiments of the present invention for controlling harmful plants or for plant growth regulation also includes the case where the active compound of formula (I) or its salt is not formed from a precursor substance ("prodrug") until after application to the plant, in the plant or in the soil.

[0047] Embodiments of the present invention also provide the use of one or more compounds of formula (I) or their salts or compositions of embodiments of the present invention (as defined below) (in a method) for controlling harmful plants or for regulating plant growth, which comprises applying an effective amount of one or more compounds of formula (I) or their salts to plants (harmful plants, if appropriate, together with useful plants), plant seeds, soil in which plants grow or on the soil or cultivation area.

[0048] IV. Compositions containing compounds of general formula (I) and / or their salts and methods of preparation and use thereof

[0049] The present invention also provides a herbicidal composition, comprising the compound of the general formula (I) as an active ingredient. In some embodiments, the mass percentage of the compound in the herbicidal composition is 0.1%-99%, such as 0.5%-95%, 1%-90%, 2%-80%, etc. In some embodiments, the herbicidal composition also includes a safener. In one or more exemplary embodiments, the present invention provides a composition for weed control and / or plant growth regulation, wherein the composition comprises:

[0050] (a) one or more compounds of formula (I) as defined above and / or their salts, in each case as defined above; and (b) one or more further substances selected from (i) and / or (ii):

[0051] (i) one or more other agrochemical active substances, which may be selected from insecticides, acaricides, nematicides, other herbicides (i.e. those not corresponding to formula (I) as defined above), fungicides, safeners, fertilizers and / or other growth regulators;

[0052] (ii) one or more formulation auxiliaries customary in crop protection.

[0053] Herein, the other agricultural chemical active substances of component (i) of the composition of the embodiments of the present invention can be selected from the substances mentioned in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0054] The herbicidal or plant growth regulating composition of the embodiment of the present invention may contain one, two, three or more formulation adjuvants (ii) commonly used in crop protection, which are selected from surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dust removers, solid carriers at 25° C. and 1013 mbar, adsorbent granular inert materials, wetting agents, antioxidants, stabilizers, buffer substances, defoamers, water, organic solvents, and organic solvents that can be miscible with water in any proportion at 25° C. and 1013 mbar.

[0055] In some embodiments, the compound (I) of the embodiment of the present invention can be used in the form of a wettable powder, an emulsifiable concentrate, a sprayable solution, a powder or a granule in a conventional formulation. Therefore, the embodiment of the present invention also provides a composition for weed control and plant growth regulation, which comprises a compound of formula (I) and / or a salt thereof.

[0056] The compounds of formula (I) and / or their salts can be formulated in various ways depending on the desired biological and / or physicochemical parameters. Possible formulations include, for example, wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water emulsions and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil-based or water-based dispersions, oil-soluble solutions, capsule suspensions (CS), dusts (DP), seed dressings, granules for broadcasting and soil application, granules in microgranular form (GR), spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV preparations, microcapsules and waxes.

[0057] In some embodiments, wettable powders are preparations that can be uniformly dispersed in water, which contain, in addition to the active compound, a diluent or inert substance, and an ionic surfactant and / or a nonionic surfactant (wetting agent, dispersant), such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkyl sulfonates, alkylbenzene sulfonates, sodium lignin sulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. To prepare wettable powders, the herbicidal active ingredient is finely ground in, for example, conventional equipment such as a hammer mill, a wind mill and an air jet mill, and simultaneously or subsequently mixed with formulation adjuvants.

[0058] In some embodiments, the emulsifiable concentrate is prepared by dissolving the active compound in an organic solvent (e.g., butanol, cyclohexanone, dimethylformamide, xylene or a higher boiling aromatic compound or hydrocarbon) or a mixture of organic solvents and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of useful emulsifiers are calcium alkylaryl sulfonates, such as calcium dodecylbenzene sulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensates, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.

[0059] In some embodiments, dusts are obtained by grinding the active compound with finely divided solids, such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0060] In some embodiments, suspension concentrates may be water-based or oil-based. They may be prepared, for example, by wet grinding using a commercially available ball mill, and optionally adding surfactants such as those listed above in other dosage forms.

[0061] In some embodiments, emulsions, such as oil-in-water emulsions (EWs), can be prepared, for example, with the aid of a stirrer, a colloid mill and / or a static mixer using an aqueous organic solvent as listed above, for example, with respect to other dosage forms, and optionally a surfactant.

[0062] In some embodiments, granules can be prepared by spraying the active compound on an adsorbable granular inert material, or by coating the active compound concentrate on the surface of a carrier (e.g., sand, kaolin or granular inert material) using a binder (e.g., polyvinyl alcohol, sodium polyacrylate or mineral oil). Suitable active compounds can also be prepared into granules in a conventional manner for preparing fertilizer granules, and can be mixed with fertilizers if necessary.

[0063] In some embodiments, water-dispersible granules can be generally prepared by conventional methods such as spray drying, fluidized bed granulation, pan granulation, mixing using a high-speed mixer, and extrusion without using a solid inert substance.

[0064] In one or more exemplary embodiments, the agricultural chemical formulations of the embodiments of the present invention, optionally a herbicidal or plant growth regulating composition, contain an active compound of formula (I) and its salts thereof in a total amount of 0.1 to 99% by weight, such as 0.5 to 95% by weight, 1 to 90% by weight, 2 to 80% by weight.

[0065] In wettable powders, the concentration of the active compound is, for example, about 10 to 90% by weight, and the balance to 100% by weight is composed of conventional formulation ingredients. In emulsifiable concentrates, the concentration of the active compound can be, for example, about 1 to 90% by weight, 5 to 80% by weight. The formulation in the form of a powder contains, for example, 1 to 30% by weight of the active composition, usually 5 to 20% by weight of the active compound. The sprayable solution contains, for example, about 0.05 to 80% by weight, 2 to 50% by weight of the active compound. For water-dispersible granules, the content of the active compound depends in part on whether the active compound is in liquid or solid form, as well as the granulation aids, fillers, etc. used. In water-dispersible granules, the content of the active compound is, for example, 1 to 95% by weight, 10 to 80% by weight.

[0066] In some embodiments, the active compound preparation mentioned optionally contains corresponding conventional tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents that affect pH and viscosity. Examples of formulation adjuvants are particularly described in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998).

[0067] In one or more exemplary embodiments, the compound of formula (I) or its salt can be used as is or in the form of its formulation (formulation) in combination with other pesticide active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators, for example in the form of finished formulations or tank mixes. Combination formulations can be prepared based on the above formulations, taking into account the physical properties and stability of the active compounds to be combined.

[0068] In some embodiments, in a mixture formulation or tank mix, the active compound that can be used in combination with the compound of formula (I) of the embodiments of the present invention is, for example, a known active compound based on the inhibition of the following enzymes, such as acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described in, for example, Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.

[0069] Of particular concern is the selective prevention and treatment of harmful plants in crops of useful plants and ornamental plants. Although in many crops, the compound (I) of the embodiment of the present invention has very good or even sufficient selectivity, in principle, in some crops, particularly in the case of a mixture with other low-selectivity herbicides, phytotoxicity for crop plants may still occur. In this regard, the composition of the compound (I) of the embodiment of the present invention comprising compound (I) or its composition with other herbicides or pesticides and safeners is of particular concern. The safener used in a detoxification effective dose can reduce the phytotoxic side effects of the herbicides / pesticides used in, for example, economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), beets, sugarcane, rapeseed, cotton and soybeans, illustratively cereals.

[0070] In some embodiments, the weight ratio of herbicide (mixture) to safener generally depends on the herbicide application rate and the efficacy of the safener, and can vary over a wide range, such as 200:1 to 1:200, 100:1 to 1:100, 20:1 to 1:20. Similar to compound (I) or a mixture thereof, safeners can be formulated with other herbicides / pesticides and provided and used as a finished formulation or as a tank mix with a herbicide.

[0071] For use, the commercially available herbicides or herbicide / safener preparations are diluted, if appropriate, in a customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersibles and water-dispersible granules. Dust preparations, granules for soil application or granules for broadcasting and sprayable solutions generally do not require further dilution with other inert substances before application.

[0072] The application rate of the compound of formula (I) and / or its salt is affected by external conditions such as temperature, humidity, etc. to a certain extent. Herein, the application rate can change in a wide range. In some embodiments, for the application of the herbicide as a harmful plant control, the total amount of the compound of formula (I) and its salt is, for example, 0.001 to 10.0 kg / ha, 0.005 to 5 kg / ha, 0.01 to 1.5 kg / ha, 0.05 to 1 kg / ha. This is applicable to application before and after emergence.

[0073] In some embodiments, when the compound of formula (I) and / or its salt is used as a plant growth regulator, for example as a stalk stabilizer for crop plants such as those described above, exemplarily cereal plants (such as wheat, barley, rye, triticale, millet, rice or corn), the total application rate is, for example, 0.001 to 2 kg / ha, 0.005 to 1 kg / ha, 10 to 500 g / ha, 20 to 250 g / ha. This applies to pre-emergence and post-emergence applications.

[0074] Application as a stem stabilizer can be carried out at various stages of plant growth, for example, after the tillering stage, at the beginning of longitudinal growth.

[0075] Alternatively, application as a plant growth regulator can also be by treating the seeds, which includes various techniques for dressing and coating the seeds. In this context, the application rate depends on the specific technique and can be determined in preliminary tests.

[0076] In some embodiments, in the composition of the embodiments of the present invention (e.g., in the form of a mixed preparation or tank mix), the active compound that can be used in combination with the compound of formula (I) of the embodiments of the present invention is, for example, a known active compound based on the inhibition of the following enzymes, the enzymes being, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.

[0077] In some embodiments, known herbicides or plant growth regulators that can be combined with the compounds of the embodiments of the present invention are, for example, the following active compounds, wherein the compounds are represented by the "common name" specified by the International Organization for Standardization (ISO) or by its chemical name or its code. They generally include all forms of use, such as acids, salts, esters, and all isomers (e.g., stereoisomers and optical isomers), even if not explicitly mentioned.

[0078] Examples of known herbicides or plant growth regulators that can be used in combination with the compounds of formula I of the embodiments of the present invention are:

[0079] b1) lipid biosynthesis inhibitors selected from the group consisting of clodinafop, clodinafop-propargyl, cyhalofop, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, and phenoxydim;

[0080] b2) ALS inhibitors selected from the group consisting of bensulfuron, bispyribac, cinosulfuron, cloransulam, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, ulfuron), florasulam, flucarbazone, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, mesosulfuron, metosulam, metsulfuron, metsulfuron-methyl yl), nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyrimisulfan, pyriftalid, imazapic imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, pyrazosulfuron-ethyl;

[0081] b3) selected from the group consisting of the following photosynthesis inhibitors: ametryn, amicarbazone, atrazine, bromoxynil and its salts and esters, chlorobromuron, chloridazone, cyanazine, diquat-dibromide, diuron, fluometuron, ioxynil and its salts and esters, isoproturon, turon), lenacil, linuron, metamitron, methabenzthiazuron, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, terbacil, terbuthylazine;

[0082] b4) a protoporphyrinogen-IX oxidase inhibitor selected from the group consisting of bencarbazone, benzfendizone, butafenacil, cinidon-ethyl, fuazolate, flufenpyr-ethyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, oxadiazon, oxyfluorfen, pentoxazone, profuazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil;

[0083] b5) bleaching agent herbicides selected from the group consisting of aclonifen, beflubutamid, benzofenap, clomazone, diflufenican, fluridone, fluchloridone, flurochloridone, mesotrione, norflurazon, picolinafen, pyrachlor sulfutole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, bixlozone, triazosulfone, cyproconazole, bispyribac, 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one (H-7;

[0084] b6) EPSP synthase inhibitors selected from the group consisting of glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);

[0085] b7) glutamine synthetase inhibitors selected from the group consisting of bilanaphos (bialaphos), bilanaphos-sodium, glufosinate-ammonium;

[0086] b8) DHP synthase inhibitors selected from the group consisting of asulam;

[0087] b9) a mitotic inhibitor selected from the group consisting of benfluralin, butralin, chlorpropham, dinitramine, dithiopyr, propham, propyzamide, tebutam, thiazopyr and trifluralin;

[0088] b10) VLCFA inhibitors selected from the group consisting of acetochlor, alachlor, anilofos, butachlor, dimethanamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone;

[0089] b11) a cellulose biosynthesis inhibitor selected from the group consisting of chlorthiamid, dichlobenil, flupoxam and isoxaben;

[0090] b12) a dissociating agent herbicide selected from the group consisting of dinoseb, dinoterb and DNOC and its salts;

[0091] b13) is selected from the following auxin herbicides: 2,4-D and its salts and esters, 2,4-DB and its salts and esters, benazolin-ethyl, clomeprop, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr -meptyl), MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid;

[0092] b14) an auxin transport inhibitor selected from the group consisting of diflufenzopyr and naptalam;

[0093] b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, endothal and its salts, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, indanofan, maleichydrazide, mefluidide, methyl-dymron, oxaziclomefone, pelargonic acid, pyributicarb, and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (H-10);

[0094] Optionally, the safener is benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, cloquintocet, pyraclostrobin, cyprosulfamide, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (H-11; MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (H-12; R-29148, CAS 52836-31-4).

[0095] Active compounds of groups b1) to b15) and safeners are known herbicides and safeners, see for example The Compendium of Pesticide Common Names; (http: / / www.alanwood.net / pesticides / ); B. Hock, C. Fedtke, RR Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart, 1995. Other herbicidally active compounds are known from WO 96 / 26202, WO 97 / 41116, WO 97 / 41117, WO 97 / 41118, WO 01 / 83459 and WO 2008 / 074991, W. et al. (eds.) "Modern Crop Protection Compounds", Vol. 1, Wiley VCH, 2007 and the literature cited therein.

[0096] Compared with the prior art, the embodiments of the present invention have the following beneficial effects:

[0097] (1) The compounds provided in the embodiments of the present invention have good activity in controlling harmful plants and good compatibility with crop plants, and are effective, efficient and broad-spectrum in controlling grass weeds and have good compatibility with crop plants.

[0098] (2) The compounds or herbicidal compositions provided in the embodiments of the present invention have good control effects on barnyard grass, foxtail grass, crabgrass, Amaranthus retroflexus, etc., and can be used in wheat, soybean, rice, corn fields, etc. to control various malignant weeds.

[0099] The following examples illustrate the compounds of formula I and embodiments of the present invention, but the present invention is not limited to the examples shown. DETAILED DESCRIPTION

[0100] The following examples are provided to illustrate the present invention and should not be construed as limiting the present invention in any way.

[0101] In view of the economic efficiency and diversity of the compounds, we preferably synthesized some compounds, and among the many synthesized compounds, some are selected and listed in the following Table 1. 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 not for limiting the present invention. For those skilled in the art, this should not be understood as the scope of the above subject matter of the present invention is limited to the following compounds.

[0102] Table 1

[0103]

[0104]

[0105] 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 purchased from the market or can be prepared by methods known in the literature or as shown in the detailed description. It will be appreciated 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 raw materials and conditions in the synthetic route have been described below, it can be easily replaced with other similar raw materials and conditions, and these modifications or variations of the preparation method of the present invention such as various isomers of compounds are included within the scope of the present invention. In addition, the preparation method described below can be further modified according to the content of the embodiments of the present invention, using conventional chemical methods well known to those skilled in the art. For example, appropriate groups are protected during the reaction, etc.

[0106] The method examples provided below are used to promote further understanding of the preparation method of the present invention. The specific substances, types and conditions used are determined to further illustrate the present invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds shown in the following table can be purchased commercially or can be easily prepared by a person of ordinary skill in the art.

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

[0108] Synthesis Example

[0109] Example 1: Preparation of Compound 1

[0110] Step 1

[0111]

[0112] 9.24 g of 3-amino-2-chloro-4-(trifluoromethoxy)benzoic acid (prepared by the method provided by patent WO2022238178A1) was added to a 250 ml four-necked flask, and 5 g of triethylamine and 100 g of dichloromethane were added in sequence. Under an ice bath, 5.9 g of tetrahydropyran-4-carbonyl chloride was slowly added dropwise. After the addition was completed, the reaction was continued at room temperature with stirring for 4 hours, and then 100 g of water was added for washing and the layers were separated. The organic layer was concentrated to obtain 11.2 g of the target product.

[0113] Step 2

[0114]

[0115] 180 ml of toluene was added to 16.3 g (36.7 mmol) of phosphorus pentasulfide, 6.50 g (61.4 mmol) of sodium carbonate was added thereto and the resulting mixture was stirred at room temperature for 5 minutes. 11.2 g (30 mmol) of 2-chloro-3-(tetrahydropyran-4-carboxamido)-4-(trifluoromethoxy)benzoic acid was added thereto and the resulting mixture was stirred at 50°C for 16 hours. 150 ml of ethyl acetate was added to the reaction solution, the resulting mixture was stirred at 50°C for 10 minutes, 100 ml of water was added, and the pH was adjusted to 3-4 with hydrochloric acid. The mixture was transferred to a separatory funnel, separated, and then the organic layer was concentrated under reduced pressure. 120 ml of water was added thereto to precipitate crystals. The mixture was stirred at room temperature for 1 hour, and then the crystals were collected, washed twice with 100 ml of water, and dried under reduced pressure at 60°C for 2 hours to obtain the target compound. The amount obtained was 10.2 g.

[0116] Step 3

[0117]

[0118] 10.2 g of 2-chloro-3-(tetrahydropyran-4-thiocarboxamido)-4-(trifluoromethoxy)benzoic acid was added to a 250 ml four-necked flask, and 10 g of thionyl chloride, 2 drops of DMF, and 100 g of petroleum ether were added in sequence. The temperature was raised to 60 ° C and stirred for 4 hours. After TLC detection, the reaction was completed, the petroleum ether was removed, and then 100 g of dichloromethane and 2.8 g of 1-methyltetrazol-5-amine were added. Under an ice bath, 3.5 g of triethylamine was slowly added. After the addition was completed, the reaction was continued to stir at room temperature for 4 hours, and then 80 g of water was added and separated. The organic layer was concentrated. 80 ml of water was added thereto to precipitate crystals. The mixture was stirred at room temperature for 1 hour, and then the crystals were collected, washed twice with 80 ml of water, and dried under reduced pressure at 60 ° C for 2 hours to obtain 9.8 g of the target product. 1 H NMR (300MHz, DMSO-d6) δppm 7.45(1H,d), 7.21(1H,d), 4.03(3H,s), 3.98-3.82(2H,m), 3.58-3.40(2H,m), 2.85-2.62(1H,m), 1.86-1.64(4H,m).

[0119] Example 2: Preparation of Compound 2

[0120]

[0121] 180ml of toluene was added to 16.3g (36.7mmol) of phosphorus pentasulfide, 6.72g (63.4mmol) of sodium carbonate was added thereto and the resulting mixture was stirred at room temperature for 5 minutes. 13.9g (31mmol) of N-[2-chloro-3-[(1-methyltetrazol-5-yl)carbamoyl]-6-(trifluoromethoxy)phenyl]-tetrahydropyran-4-carboxamide (prepared by the method provided by patent WO2022238178A1) was added thereto, and the resulting mixture was stirred at 50°C for 19 hours. 150ml of ethyl acetate was added to the reaction solution, the resulting mixture was stirred at 50°C for 10 minutes, the insoluble material was filtered out, and 100 grams of water was added. The mixture was transferred to a separatory funnel, separated, and the organic layer was concentrated under reduced pressure. 100ml of water was added thereto to precipitate crystals. The mixture was stirred at room temperature for 1 hour, and then the crystals were collected and dried under reduced pressure at 60°C for 2 hours to obtain the target compound. The amount obtained was 13.7 g. 1 H NMR (300MHz, DMSO-d6) δppm7.34(1H,d), 7.12(1H,d), 4.03(3H,s), 3.98-3.85(2H,m), 3.53-3.42(2H,m), 2.79-2.67(1H,m), 1.86-1.68(4H,m).

[0122] Example 3 Preparation of Compound 3

[0123] Step 1

[0124]

[0125] 150ml of toluene was added to 16.3g (36.7mmol) of phosphorus pentasulfide, 6.72g (63.4mmol) of sodium carbonate was added thereto and the resulting mixture was stirred at room temperature for 5 minutes. 21.2g (63mmol) of 3-amino-2-chloro-N-(1-methyltetrazol-5-yl)-4-(trifluoromethoxy)benzamide (prepared by the method provided by patent WO2022238178A1) was added thereto, and the resulting mixture was stirred at 50°C for 16 hours. 150ml of ethyl acetate was added to the reaction solution, the resulting mixture was stirred at 50°C for 10 minutes, the insoluble material was filtered out, and 100 grams of water was added. The mixture was transferred to a separatory funnel, separated, and the organic layer was concentrated under reduced pressure. 100ml of water was added thereto to precipitate crystals. The mixture was stirred at room temperature for 1 hour, and then the crystals were collected and dried under reduced pressure at 60°C for 2 hours to obtain the target compound. The amount obtained was 20.8g.

[0126] Step 2

[0127]

[0128] Add 17.6 g of 3-amino-2-chloro-N-(1-methyltetrazol-5-yl)-4-(trifluoromethoxy)thiobenzamide to a 250 ml four-necked flask, add 6.5 g of triethylamine and 100 g of dichloromethane in sequence, and slowly drop 7.8 g of tetrahydropyran-4-carbonyl chloride under an ice bath. After the addition is complete, continue to stir the reaction at room temperature for 4 hours, then add 100 g of water and separate the layers. The organic layer is concentrated, and 100 ml of water is added thereto to precipitate crystals. The mixture is stirred at room temperature for 1 hour, and then the crystals are collected and dried under reduced pressure at 60°C for 2 hours to obtain the target compound. The amount obtained is 19.75 g. 1 H NMR (300MHz, DMSO-d6) δppm 7.24(1H,d), 7.10(1H,d), 4.03(3H,s), 3.98-3.85(2H,m), 3.53-3.42(2H,m), 2.79-2.67(1H,m), 1.86-1.68(4H,m).

[0129] Example 4 Preparation of Compound 4

[0130] Step 1

[0131]

[0132] 9.5 g of 3-amino-2-chloro-4-(difluoromethoxy)benzoic acid (prepared by the method provided by patent WO2022238178A1) was added to a 250 ml four-necked flask, and 5 g of triethylamine and 100 g of dichloromethane were added in sequence. Under an ice bath, 6.24 g of tetrahydropyran-4-carbonyl chloride was slowly added dropwise. After the addition was completed, the reaction was continued at room temperature with stirring for 4 hours, and then 100 g of water was added for washing and the layers were separated. The organic layer was concentrated to obtain 12.4 g of the target product.

[0133] Step 2

[0134]

[0135] 150 ml of toluene was added to 16.3 g (36.7 mmol) of phosphorus pentasulfide, 6.50 g (61.4 mmol) of sodium carbonate was added thereto and the resulting mixture was stirred at room temperature for 5 minutes. 12.4 g (35 mmol) of 2-chloro-3-(tetrahydropyran-4-carboxamido)-4-(difluoromethoxy)benzoic acid was added thereto and the resulting mixture was stirred at 50°C for 16 hours. 150 ml of ethyl acetate was added to the reaction solution, the resulting mixture was stirred at 50°C for 10 minutes, 100 ml of water was added, and the pH was adjusted to 3-4 with hydrochloric acid. The mixture was transferred to a separatory funnel, separated, and then the organic layer was concentrated under reduced pressure. 120 ml of water was added thereto to precipitate crystals. The mixture was stirred at room temperature for 1 hour, and then the crystals were collected, washed twice with 100 ml of water, and dried under reduced pressure at 60°C for 2 hours to obtain the target compound. The amount obtained was 11.2 g.

[0136] Step 3

[0137]

[0138] 11.2 g of 2-chloro-3-(tetrahydropyran-4-thiocarboxamido)-4-(trifluoromethoxy)benzoic acid was added to a 250 ml four-necked flask, and 12 g of thionyl chloride, 2 drops of DMF, and 100 g of petroleum ether were added in sequence. The temperature was raised to 60 ° C and stirred for 4 hours. After TLC detection, the reaction was completed, the petroleum ether was removed, and then 100 g of dichloromethane and 3.2 g of 1-methyltetrazol-5-amine were added. Under an ice bath, 5 g of triethylamine was slowly added. After the addition was completed, the reaction was continued to stir at room temperature for 4 hours, and then 100 g of water was added and the layers were separated. The organic layer was concentrated. 80 ml of water was added thereto to precipitate crystals. The mixture was stirred at room temperature for 1 hour, and then the crystals were collected, washed with 100 ml of water, and dried under reduced pressure at 60 ° C for 2 hours to obtain 10.8 g of the target product. 1 H NMR(300MHz,DMSO-d6)δppm 7.74(1H,d), 7.38(1H,d), 7.21(1H,t), 4.02(3H,s), 4.00-3.84(2H,m), 3.48-3.20(2H,m), 2.82-2.60(1H,m), 1.83-1.62(4H,m).

[0139] Example 5 Preparation of Compound 5

[0140] Step 1

[0141]

[0142] 150ml of toluene was added to 16.3g (36.7mmol) of phosphorus pentasulfide, 6.72g (63.4mmol) of sodium carbonate was added thereto and the resulting mixture was stirred at room temperature for 5 minutes. 20.07g (63mmol) of 3-amino-2-chloro-N-(1-methyltetrazol-5-yl)-4-(difluoromethoxy)benzamide (prepared by the method provided by patent WO2022238178A1) was added thereto, and the resulting mixture was stirred at 50°C for 16 hours. 150ml of ethyl acetate was added to the reaction solution, the resulting mixture was stirred at 50°C for 10 minutes, the insoluble material was filtered out, and 100 grams of water was added. The mixture was moved to a separatory funnel, separated, and the organic layer was concentrated under reduced pressure. 100ml of water was added thereto to precipitate crystals. The mixture was stirred at room temperature for 1 hour, and then the crystals were collected and dried under reduced pressure at 60°C for 2 hours to obtain the target compound. The amount obtained was 18.8g.

[0143] Step 2

[0144]

[0145] Add 18.8 g of 3-amino-2-chloro-N-(1-methyltetrazol-5-yl)-4-(difluoromethoxy)thiobenzamide to a 250 ml four-necked flask, add 6.8 g of triethylamine and 100 g of dichloromethane in sequence, and slowly drop 8.8 g of tetrahydropyran-4-carbonyl chloride under an ice bath. After the addition is complete, continue to stir the reaction at room temperature for 4 hours, then add 100 g of water and separate the layers. The organic layer is concentrated, and 100 ml of water is added thereto to precipitate crystals. The mixture is stirred at room temperature for 1 hour, and then the crystals are collected and dried under reduced pressure at 60°C for 2 hours to obtain the target compound. The amount obtained is 22.8 g. 1 H NMR(300MHz,DMSO-d6)δppm 7.25(1H,d), 7.12(1H,d), 7.21(1H,t), 4.02(3H,s), 4.00-3.84(2H,m), 3.48-3.20(2H,m), 2.82-2.60(1H,m), 1.83-1.62(4H,m).

[0146] Example 6 Preparation of Compound 6

[0147]

[0148] 180ml of toluene was added to 16.3g (36.7mmol) of phosphorus pentasulfide, 6.72g (63.4mmol) of sodium carbonate was added thereto and the resulting mixture was stirred at room temperature for 5 minutes. 13.35g (31mmol) of N-[2-chloro-3-[(1-methyltetrazol-5-yl)carbamoyl]-6-(difluoromethoxy)phenyl]-tetrahydropyran-4-carboxamide (prepared by the method provided by patent WO2022238178A1) was added thereto, and the resulting mixture was stirred at 50°C for 19 hours. 150ml of ethyl acetate was added to the reaction solution, the resulting mixture was stirred at 50°C for 10 minutes, the insoluble material was filtered out, and 100 grams of water was added. The mixture was transferred to a separatory funnel, separated, and the organic layer was concentrated under reduced pressure. 100ml of water was added thereto to precipitate crystals. The mixture was stirred at room temperature for 1 hour, and then the crystals were collected and dried under reduced pressure at 60°C for 2 hours to obtain the target compound. The amount obtained was 12.85 g. 1 H NMR (300MHz, DMSO-d6) δppm7.28 (1H, d), 7.15 (1H, d), 7.21 (1H, t), 4.02 (3H, s ), 4.00-3.84(2H,m), 3.48-3.20(2H,m), 2.86-2.62(1H,m), 1.83-1.62(4H,m).

[0149] Example 7 Preparation of Compound 2 Sodium Salt

[0150]

[0151] 24 g of N-[2-chloro-3-[(1-methyltetrazol-5-yl)carbamoyl]-6-(trifluoromethoxy)phenyl]-tetrahydropyran-4-carboxamide was added to a 250 ml four-necked flask, followed by 4.5 g of sodium hydroxide, 45 g of water, and 100 g of toluene. The mixture was stirred at room temperature for 4 hours and the reaction was completed by TLC detection. The layers were separated. The water layer was dried to obtain 24.98 g of the target product.

[0152] II. Application Examples

[0153] Example 8: Pre-emergence herbicidal effect

[0154] Control compound CK It is an invention example compound in WO2022238178A1.

[0155] Seeds of monocotyledonous and dicotyledonous weed plants or crop plants are placed in sandy loam in wood fiber pots and covered with soil. Then, the compounds of the general formula (I) of the examples of the present invention prepared in Examples 1-4 and the control compound CK are sprayed on the surface of the soil in the form of an aqueous suspension or emulsion (with the addition of 0.2% of a wetting agent) at an application rate of 600 liters of water / hectare (converted). After treatment, the pots are placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparation is visually evaluated (in percentage) by comparison with the control group. For example, 100% activity = plant has died, 50% herbicidal activity or damage = plant reduction to 50% or plant material reduction by 50%, 0% activity = similar to the control plant.

[0156] Table 2 Pre-emergence herbicidal effects of the compounds of general formula (I) of the examples of the present invention compared with the control compounds: (dosage: 200 g / ha)

[0157]

[0158]

[0159] It can be seen from Table 2 that after pre-emergence soil treatment, the herbicidal activity of the compounds of the examples of the present invention is much better than that of the control compounds. At the same time, compared with the control compounds, the compounds of the examples of the present invention have better safety to rice and wheat.

[0160] Example 9: Post-emergence herbicidal effect

[0161] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are placed in sandy loam in wood fiber pots, covered with soil and then cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the single leaf stage and sprayed with the compounds of the general formula (I) of the examples of the invention formulated in Examples 1 to 4 and the control compound CK in the form of an aqueous suspension or emulsion (with the addition of 0.2% of a wetting agent) at an application rate of 600 liters of water / hectare (converted) on the green parts of the plants. The test plants are then placed in a greenhouse under optimal growth conditions for about 3 weeks and the effect of the formulation is assessed visually (in percentage) by comparison with the control group. For example, 100% activity = plant death, 50% herbicidal activity or damage = plant reduction to 50% or plant material reduction to 50%, 0% activity = similar to the control plants.

[0162] Table 3 Post-emergence herbicidal effects of the compounds of general formula (I) of the present invention compared with the control compounds: (dosage: 50 g / ha)

[0163] serial number Barnyard grass Crataegus Channa intestine Amaranthus retroflexus Cyperus rotundus Rice* 1 94.7 96.3 95.8 100 90.2 2 2 92.4 94.2 96.5 98.3 88.4 0 3 93.4 93.8 94.3 95.2 89.6 0 4 94.2 94.5 92.8 100 90.2 5 5 92.6 90.2 90.5 94.8 88.2 5 6 95.2 89.2 93.4 100 89.6 0 CK 89.2 86 83 94 80.8 10

[0164] Note: Rice* (Dosage: 300g / ha)

[0165] It can be seen from Table 3 that after the treatment of stems and leaves after emergence, the herbicidal activity of the compounds of the examples of the present invention is much better than that of the control compounds. At the same time, compared with the control compounds, the compounds of the examples of the present invention have better safety to rice and wheat.

[0166] It can be seen that the compounds of the examples of the present invention, whether applied before or after emergence, achieved a herbicidal effect far superior to that of the control compounds, and at the same time had good safety to crop plants.

[0167] The embodiments of the present invention provide a compound with herbicidal activity, a herbicidal composition comprising the compound, and uses thereof. The compound has broad-spectrum herbicidal activity and has good control effects on barnyard grass, foxtail grass, crabgrass, Amaranthus retroflexus, etc., and can be used in wheat, soybeans, rice, corn, orchards, and non-arable land to control various malignant weeds.

[0168] Finally, it should be noted that: although specific embodiments have been used to illustrate and describe the embodiments of the present invention, it should be appreciated that the above embodiments are only used to illustrate the technical solutions of the embodiments of the present invention, rather than to limit them; those skilled in the art should understand that: without departing from the spirit and scope of the embodiments of the present invention, the technical solutions recorded in the aforementioned embodiments may be modified, or some or all of the technical features therein may be replaced by equivalents; and these modifications or replacements do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present invention.

Claims

1. A novel thioamide compound represented by general formula I or an agriculturally acceptable salt thereof: characterized in that: Where: R1 is selected from halogenated C1-C3 alkyl; R2, R3 are selected from O, S; and R2, R3 are not selected from O, at least one is selected from S; R4 is selected from methyl or ethyl.

2. The novel thioamide compound or its agriculturally acceptable salt according to claim 1, characterized in that: In the general formula (I) R1 is selected from trifluoromethane and difluoromethane; R2, R3 are respectively selected from O, S; and R2, R3 are not selected from O at the same time, at least one is selected from S; R4 is selected from methyl or ethyl.

3. The novel thioamide compound or its agriculturally acceptable salt according to claim 2, characterized in that: Selected from the following structures: 。 4. The novel thioamide compound or its agriculturally acceptable salt according to any one of claims 1 to 3, characterized in that: The salt of the compound represented by the general formula (I) is selected from the group consisting of a sodium salt, a potassium salt, a calcium salt and a lithium salt of the compound represented by the general formula (I).

5. Use of the novel thioamide compound or its agriculturally acceptable salt according to any one of claims 1 to 4 for treating stems and leaves before or after emergence to control weeds.

6. A herbicidal composition, characterized in that: The novel thioamide compound or its agriculturally acceptable salt as claimed in any one of claims 1 to 4 is used as an active component.

7. The herbicidal composition according to claim 6, characterized in that The mass percentage of the compound in the herbicidal composition is 0.1%-99%.

8. The herbicidal composition according to claim 6, characterized in that The mass percentage of the compound in the herbicidal composition is 0.5%-95%.

9. The herbicidal composition according to claim 6, characterized in that The mass percentage of the compound in the herbicidal composition is 1%-90%.

10. The herbicidal composition according to claim 6, characterized in that The mass percentage of the compound in the herbicidal composition is 2%-80%.

11. The herbicidal composition according to any one of claims 6 to 9, characterized in that: The herbicidal composition also includes a safener.

12. The herbicidal composition according to claim 6, characterized in that The herbicidal composition further comprises one or more selected from the following agricultural chemical active substances: insecticides, miticides, nematicides, fungicides, fertilizers, other herbicides and other plant growth regulators.

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