WO2022012320A1 - Composé, composition herbicide et utilisation associée - Google Patents

Composé, composition herbicide et utilisation associée Download PDF

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Publication number
WO2022012320A1
WO2022012320A1 PCT/CN2021/102898 CN2021102898W WO2022012320A1 WO 2022012320 A1 WO2022012320 A1 WO 2022012320A1 CN 2021102898 W CN2021102898 W CN 2021102898W WO 2022012320 A1 WO2022012320 A1 WO 2022012320A1
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compound
herbicidal composition
general formula
plants
present disclosure
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PCT/CN2021/102898
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English (en)
Chinese (zh)
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周银平
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周银平
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms

Definitions

  • the present disclosure relates to the technical field of agricultural herbicides, and in particular, to a compound, a herbicidal composition and use thereof.
  • the present disclosure provides a compound comprising any one of the compound represented by the general formula (I), the N-oxide of the compound represented by the general formula (I), and the salt of the compound represented by the general formula (I). kind;
  • X is selected from O or S
  • R 1 and R 2 are the same or different, and are independently selected from halogen, hydrogen, hydroxyl, C 1 -C 6 alkylamino, halogenated C 1 -C 6 alkylamino, C1-C 6 alkoxy, halogenated C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halogenated C 1 -C 6 alkylthio, C 2 -C 6 alkenyloxy, halogenated C 2 -C 6 alkenyloxy , C 2 -C 6 alkynyloxy, halogenated C 2 -C 6 alkynyloxy.
  • X is O
  • R 1 and R 2 are the same or different, and are independently selected from: halogen, hydrogen, hydroxyl, C 1 -C 4 alkoxy, and halogenated C 1 -C 4 alkoxy.
  • X is O
  • R 1 and R 2 are the same or different, and are independently selected from F, Cl, Br, I, H, hydroxyl, methoxy, ethoxy, propoxy, butoxy, trifluoromethoxy, trifluoro One of ethoxy, difluoromethoxy or difluoroethoxy.
  • X is O
  • R 1 and R 2 are the same or different, and are independently selected from F, Cl, Br, H, hydroxyl, methoxy, ethoxy, trifluoromethoxy or difluoromethoxy.
  • X is O
  • R 1 and R 2 are the same or different, and are independently selected from: Cl, H, hydroxyl, and difluoromethoxy.
  • the salt of the compound shown in general formula (I) is selected from a kind of in sodium salt, potassium salt, calcium salt and lithium salt of the compound shown in general formula (I), preferably sodium salt, potassium salt and one of the lithium salts.
  • the present disclosure also provides a herbicidal composition comprising the compound as an active ingredient.
  • the mass percentage of the compound in the herbicidal composition is 0.1%-99%, such as 0.5%-95%, 1%-90%, 2%-80%, and the like.
  • the herbicidal composition further includes a safener.
  • the herbicidal composition further comprises one or more selected from the following agrochemical active substances: insecticides, acaricides, nematicides, fungicides, fertilizers, other herbicides and other plants growth regulator.
  • the herbicidal composition further comprises one or more selected from the following formulation adjuvants: surfactants, emulsifiers, dispersants, film-forming agents, thickeners, inorganic salts, dust removers, Solid carrier, adsorbent particulate inert material, wetting agent, antioxidant, stabilizer, buffer substance, defoamer, water, organic solvent at 25° C. and 1013 mbar.
  • formulation adjuvants include surfactants, emulsifiers, dispersants, film-forming agents, thickeners, inorganic salts, dust removers, Solid carrier, adsorbent particulate inert material, wetting agent, antioxidant, stabilizer, buffer substance, defoamer, water, organic solvent at 25° C. and 1013 mbar.
  • the use forms of the herbicidal composition include wettable powders, emulsifiable concentrates, sprayable solutions, powders or granules.
  • the present disclosure also provides the use of the compound or the herbicidal composition in weed control.
  • the compound or the herbicidal composition is used to control harmful plants in crops of useful or ornamental plants and their transgenic crops.
  • the compound or the herbicidal composition is used to control wheat, barley, rye, oat, triticale, millet, rice, cassava, corn, sugar beet, sugar cane, rape, potato, tomato, pea, cotton and Harmful plants in soybeans.
  • the compound or the herbicidal composition is used to control broadleaf weeds and grass weeds.
  • the compound or the herbicidal composition is used to control barnyardgrass, foxtail, crabgrass, amaranth, sedge and snakehead.
  • the present disclosure provides a compound comprising any one of the compound represented by the general formula (I), the N-oxide of the compound represented by the general formula (I), and the salt of the compound represented by the general formula (I). kind;
  • X is selected from O or S
  • R 1 and R 2 are the same or different and are independently selected from halogen, hydrogen, hydroxyl, C 1 -C 6 alkylamino, halogenated C 1 -C 6 alkylamino, C1-C 6 alkoxy, halogenated C 1- C 6 alkoxy, C 1 -C 6 alkylthio, halogenated C 1 -C 6 alkylthio, C 2 -C 6 alkenyloxy, halogenated C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, halogenated C 2 -C 6 alkynyloxy.
  • X is O
  • R 1 and R 2 are the same or different and are independently selected from: halogen, hydrogen, hydroxyl, C 1 -C 4 alkoxy, halogenated C 1 -C 4 alkoxy.
  • X is O
  • R 1 and R 2 are the same or different and are independently selected from F, Cl, Br, I, H, hydroxyl, methoxy, ethoxy, propoxy, butoxy, trifluoromethoxy, trifluoroethyl One of oxy, difluoromethoxy or difluoroethoxy.
  • X is O
  • R 1 and R 2 are the same or different, and are independently selected from F, Cl, Br, H, hydroxyl, methoxy, ethoxy, trifluoromethoxy or difluoromethoxy.
  • X is O
  • R 1 and R 2 are the same or different, and are independently selected from: Cl, H, hydroxyl, and difluoromethoxy.
  • the salt of the compound represented by the general formula (I) is selected from one of the sodium salts, potassium salts, calcium salts and lithium salts of the compound represented by the general formula (I), optionally sodium One of salt, potassium salt and lithium salt.
  • tautomers may form due to the presence of conjugated chemical bonds, and the present disclosure includes tautomers and mixtures thereof in any ratio.
  • Halogen refers to fluorine, chlorine, bromine or iodine.
  • Alkyl Linear, branched or cyclized alkyl, such as methyl, ethyl, propyl, isopropyl, tert-butyl or cyclopropyl.
  • Haloalkyl straight or branched chain haloalkyl, the hydrogen atoms on these alkyl groups may be partially or fully substituted by halogen atoms, for example, haloalkyl groups such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl group, difluoromethyl or trifluoromethyl.
  • Alkoxy Linear, branched or cyclic alkoxy, for example methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy or cyclopropoxy.
  • Haloalkoxy straight or branched chain haloalkoxy, the hydrogen atoms in these alkoxy groups may be partially or fully substituted by halogen atoms, for example, haloalkyl groups such as chloromethoxy, dichloromethoxy, trichloro Methoxy, fluoromethoxy, difluoromethoxy or trifluoromethoxy.
  • Alkylthio A straight or branched chain alkyl group attached to the structure via a sulfur atom bond.
  • Halogenated alkylthio group straight-chain or branched-chain alkylthio group, the hydrogen atoms on these alkylthio groups may be partially or totally substituted by halogen atoms.
  • halogen atoms for example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like.
  • Alkenyl straight or branched chain and may have a double bond in any position, such as vinyl or allyl.
  • Alkynyl straight or branched chain and may have triple bonds in any position, such as ethynyl or propargyl.
  • bases that can form salts with compounds represented by formula (I) of the present disclosure include: sodium hydroxide, potassium hydroxide, lithium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate , potassium bicarbonate, lithium carbonate, etc.
  • the compound represented by general formula (I) of the present disclosure can be prepared according to the following methods:
  • the above reaction is carried out in a suitable solvent, and the suitable solvent can be selected from benzene, toluene, xylene, acetone, tetrahydrofuran, acetonitrile, N,N-dimethylformamide, N-methylpyrrolidone, dichloromethane, chloroform, Dichloroethane or ethyl acetate, etc.
  • the reaction can be carried out in the presence or absence of a base, and when the reaction is carried out in the presence of a base, the reaction can be accelerated.
  • the alkali can be selected from alkali metal hydrides, such as sodium hydride, lithium hydride or sodium amide, etc.; alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide; alkali metal carbonates, such as sodium carbonate or potassium carbonate ; Organic bases, such as pyridine, 4-dimethylaminopyridine, triethylamine, N-methylpyrrole or diisopropylethylamine, etc.
  • the reaction temperature can be between -10°C and the boiling point temperature of a suitable solvent selected in the reaction, usually 0-100°C.
  • the reaction time is 30 minutes to 20 hours, usually 1 to 10 hours.
  • the above reaction is carried out in a suitable solvent, and the suitable solvent can be selected from benzene, toluene, xylene, acetone, tetrahydrofuran, acetonitrile, N,N-dimethylformamide, N-methylpyrrolidone, dichloromethane, chloroform, Dichloroethane or ethyl acetate, etc.
  • the reaction can be carried out in the presence or absence of a base, and when the reaction is carried out in the presence of a base, the reaction can be accelerated.
  • the alkali can be selected from alkali metal hydrides, such as sodium hydride, lithium hydride or sodium amide, etc.; alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide; alkali metal carbonates, such as sodium carbonate or potassium carbonate ; Organic bases, such as pyridine, 4-dimethylaminopyridine, triethylamine, N-methylpyrrole or diisopropylethylamine, etc.
  • the reaction temperature can be between -10°C and the boiling point temperature of a suitable solvent selected in the reaction, usually 0-100°C.
  • the reaction time is 30 minutes to 20 hours, usually 1 to 10 hours.
  • the present disclosure also relates to the use of the compounds or herbicidal compositions in weed control.
  • the compounds represented by the general formula (I) and their agriculturally acceptable salts are suitable for use as herbicides in the form of mixtures of isomers and in the form of pure isomers. They are suitable for direct use or in suitably formulated compositions.
  • Herbicidal compositions comprising compounds of formula (I) are very effective in controlling plant growth in non-crop areas, especially at high application rates. They act on broadleaf and grass weeds in crops such as wheat, rice, corn, soybean and cotton without causing any significant damage to the crops. This effect is mainly observed at low application rates.
  • the compound represented by the general formula (I) of the present disclosure and/or its salt is suitable for controlling harmful plants in a wide range, such as the monocotyledonous and dicotyledonous harmful plants of the following genus, these examples are only used to illustrate the present invention Disclosure, but in no way limit this disclosure.
  • grass weeds and Seedlings of broadleaf weeds are unearthed, or they are allowed to grow until they reach the cotyledon stage and stop growing, and finally die completely after three to four weeks.
  • the active compound if the active compound is applied to the green parts of the plant after emergence, growth stops after the treatment and the harmful plant remains in the growth phase at the point of application, or completely after a period of time death, thereby continuously eliminating competition from weeds that are harmful to crop plants at a very early point in time.
  • Crop plants of the economically important crops are, for example, dicotyledonous crops of the following genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus (Miscanthus), Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the following genera: Allium, Bromeliad (Ananas), Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum (Sorghum), Triticale (Triticale), Triticum (Triticum) and Zea (Z
  • the compounds of the present disclosure (depending on their specific structure and the application rates used) have excellent growth regulating properties on crop plants. They participate in the plant's own metabolism in a regulatory role and thus can be used to control the influence of plant components and to facilitate harvesting, for example by inducing dehydration and stunted growth. Furthermore, they are suitable for general control and inhibition of unwanted vegetative growth without damaging the plants 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.
  • transgenic plants are characterized by particularly advantageous properties, such as resistance to certain pesticides: in particular certain herbicides, to plant diseases or plant disease pathogens such as certain insects or microorganisms (such as fungi, bacteria or virus) resistance.
  • Other specific properties relate to eg quantity, quality, storability, composition and specific components of the harvested material. For example, transgenic plants with increased starch content or improved starch quality, or harvested material containing different fatty acid compositions are known.
  • Other specific properties may be tolerance or resistance to abiotic stress factors, such as heat, cold, drought, salinity and UV radiation.
  • the compounds of formula (I) and/or their salts of the present disclosure are used in economically important transgenic crops of useful plants and ornamental plants, such as cereals (eg wheat, barley, rye, oats, etc.) , triticale, millet, rice, cassava and corn), or other crops such as sugar beets, cotton, soybeans, canola, potatoes, tomatoes, peas and other vegetables.
  • cereals eg wheat, barley, rye, oats, etc.
  • triticale millet, rice, cassava and corn
  • sugar beets cotton, soybeans, canola, potatoes, tomatoes, peas and other vegetables.
  • the compounds of formula (I) are used as herbicides in crops of useful plants which are resistant to the phytotoxic effects of herbicides, or for which resistance has been obtained by recombinant techniques.
  • compound (I) of the present disclosure is used in transgenic crops that are resistant to growth regulators, such as dicamba; or herbicides that inhibit plant essential enzymes, which are essential for plants
  • growth regulators such as dicamba
  • herbicides that inhibit plant essential enzymes, which are essential for plants
  • sulfonylurea glyphosate, glufosinate or benzene
  • Herbicides for formylisoxazole and similar active compounds Herbicides for formylisoxazole and similar active compounds.
  • the active compounds of the present disclosure are used in transgenic crops, not only the effects on harmful plants observed in other crops, but also often specific effects on application to the particular transgenic crop, such as altered or particularly broadened.
  • the present disclosure also relates to the use of the compounds of formula (I) of the present disclosure and/or their salts as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally transgenic crop plants.
  • the present disclosure also relates to the use of compounds of formula (I) and/or salts thereof in cereals, such as corn, wheat, barley, rye, oats, millet or rice, by pre-emergence or post-emergence methods .
  • the present disclosure also relates to the use of compounds of formula (I) and/or salts thereof in soybean by pre-emergence or post-emergence methods.
  • the use of the present disclosure for controlling harmful plants or for plant growth regulation also includes wherein the activity of formula (I) is not present until after application on, in plants or in soil.
  • a compound or a salt thereof is only formed from a precursor substance ("prodrug").
  • the present disclosure also provides the use of one or more compounds of formula (I) or a salt thereof or a composition of the present disclosure (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 the formula (I) or their salts to plants (harmful plants, if appropriate, together with useful plants), plant seeds, in or on the soil in which the plants grow or on the soil in which they are grown or cultivated area.
  • compositions comprising compounds of general formula (I) and/or salts thereof, and methods of formulation and use thereof
  • the present disclosure also provides a herbicidal composition
  • a herbicidal composition comprising the compound of general formula (I) as an active component.
  • the mass percentage of the compound in the herbicidal composition is 0.1%-99%, such as 0.5%-95%, 1%-90%, 2%-80%, and the like.
  • the herbicidal composition further includes a safener.
  • the present disclosure provides a herbicidal and/or plant growth regulating composition, wherein the composition comprises:
  • one or more other agrochemical active substances which may be selected from insecticides, acaricides, nematicides, other herbicides (ie those not corresponding to formula (I) as defined above), fungicides , safeners, fertilizers and/or other growth regulators;
  • component (i) of the composition of the present disclosure may be selected from those mentioned in "The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 substance.
  • the herbicidal or plant growth regulating composition of the present disclosure may comprise one, two, three or more formulation adjuvants (ii) commonly used in crop protection, selected from the group consisting of surfactants, emulsifiers, dispersants , film formers, thickeners, inorganic salts, dust collectors, solid carriers at 25°C and 1013 mbar, adsorbent particulate inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoaming agents , water, organic solvent, organic solvent miscible with water in any ratio at 25°C and 1013 mbar.
  • formulation adjuvants ii) commonly used in crop protection, selected from the group consisting of surfactants, emulsifiers, dispersants , film formers, thickeners, inorganic salts, dust collectors, solid carriers at 25°C and 1013 mbar, adsorbent particulate inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antif
  • Compound (I) of the present disclosure can be used in conventional formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, powders or granules. Accordingly, the present disclosure also provides herbicidal and plant growth regulating compositions comprising a compound of formula (I) and/or a salt thereof.
  • 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 and water-in-oil emulsions, sprayable solutions Agents, Suspension Concentrates (SC), Oil- or Water-Based Dispersions, Oil-Soluble Solutions, Capsule Suspensions (CS), Powders (DP), Seed Dressings, Granules for Spreading and Soil Application, Microgranular Forms granules (GR), spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powders
  • wettable powders are formulations that are homogeneously dispersible in water, and which, in addition to the active compound, contain diluents or inert substances, and ionic and/or nonionic surfactants ( wetting agents, dispersing agents) such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkylsulfonates, alkanes benzenesulfonate, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoyl methyl taurate.
  • the herbicidal active ingredient is finely ground, for example, in conventional equipment such as hammer mills, wind mills and air jet
  • the emulsifiable concentrate is prepared by dissolving the active compound in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene, or higher boiling aromatic compounds or hydrocarbons type) or organic solvent mixture, and add one or more ionic and/or non-ionic surfactants (emulsifiers).
  • organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene, or higher boiling aromatic compounds or hydrocarbons type
  • organic solvent mixture such as butanol, cyclohexanone, dimethylformamide, xylene, or higher boiling aromatic compounds or hydrocarbons type
  • ionic and/or non-ionic surfactants emulsifiers
  • useful emulsifiers are: calcium alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; or non-ionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensates, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan Alcohol esters, such as polyoxyethylene sorbitan fatty acid esters.
  • calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate
  • non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensates, alkyl polyethers
  • powders can be obtained by grinding the active compound with finely divided solids such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • the suspension concentrate may be water-based or oil-based. They can be prepared, for example, by wet milling using a commercially available ball mill, and optionally adding surfactants such as those listed above in other dosage forms.
  • emulsions such as oil-in-water emulsions (EWs)
  • EWs oil-in-water emulsions
  • agitators e.g., colloid mills, and/or static mixers, using aqueous organic solvents and optionally surface active agent.
  • granules can be prepared by spraying the active compound on an adsorbable particulate inert material, or by using a binder such as polyvinyl alcohol, sodium polyacrylate, or mineral oil to concentrate the active compound It is prepared by coating on the surface of a carrier such as sand, kaolin or granular inert material.
  • a binder such as polyvinyl alcohol, sodium polyacrylate, or mineral oil to concentrate the active compound It is prepared by coating on the surface of a carrier such as sand, kaolin or granular inert material.
  • the suitable active compounds can also be granulated in the customary manner for the preparation of fertilizer granules and, if desired, can be mixed with the fertilizer.
  • water dispersible granules can generally be prepared by conventional methods such as spray drying, fluid bed granulation, pan granulation, mixing using a high speed mixer, and using no solids Extrusion of inert substances.
  • an agrochemical formulation of the present disclosure optionally a herbicidal or plant growth regulating composition, contains 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 of the active compounds of formula (I) and their salts.
  • the active compound concentration is, for example, from about 10 to 90% by weight, the balance to 100% by weight consisting of customary formulation ingredients.
  • the concentration of active compound can be, for example, about 1 to 90% by weight, 5 to 80% by weight.
  • Formulations in powder form contain, for example, 1 to 30% by weight of active composition, usually 5 to 20% by weight of active compound.
  • Sprayable solutions contain, for example, about 0.05 to 80% by weight, 2 to 50% by weight of active compound.
  • the active compound content depends in part on whether the active compound is in liquid or solid form, and on the granulation aids, fillers, etc. used. In water-dispersible granules, the active compound content is, for example, 1 to 95% by weight, 10 to 80% by weight.
  • the active compound formulations mentioned optionally contain corresponding conventional tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze and solvents, fillers, Carriers and dyes, antifoams, evaporation inhibitors and reagents affecting pH and viscosity.
  • formulation aids are described inter alia in "Chemistry and Technology of Agrochemical Formulations", ed. D.A. Knowles, Kluwer Academic Publishers (1998).
  • the compound of formula (I) or a salt thereof may be used as such or in combination with other pesticidal active substances, such as insecticides, acaricides, or in the form of their formulations (formulations). , 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 formulations described above, taking into account the physical properties and stability of the active compounds to be combined.
  • the active compounds that can be used in combination with the compounds of formula (I) of the present disclosure in mixture formulations or tank mixes are known active compounds based, for example, on the inhibition of enzymes such as: Acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvate shikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, bougainvillea Erubin desaturases, photosystem I, photosystem II, protoporphyrinogen oxidase, as e.g. Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British CropProtection Council and the Royal As described in Soc. of Chemistry, 2012 and references cited therein.
  • compositions of compound (I) of the present disclosure comprising compound (I) or combinations thereof with other herbicides or pesticides and safeners are of particular interest.
  • Safeners used in detoxifying effective doses can reduce the phytotoxic side effects of, for example, herbicides/pesticides used in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rape, cotton and soybean, exemplarily cereals.
  • herbicides/pesticides used in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rape, cotton and soybean, exemplarily cereals.
  • the weight ratio of herbicide (mixture) to safener generally depends on the herbicide application rate and the efficacy of the safener, and can vary widely, eg, 200:1 to 1:200, 100 : 1 to 1:100, 20:1 to 1:20. Similar to compound (I) or mixtures thereof, safeners can be formulated with other herbicides/pesticides and supplied and used as finished formulations or as tank mixes with herbicides.
  • the herbicide or herbicide/safener formulations in commercial form are diluted, if appropriate, in the customary manner, eg with water in the case of wettable powders, emulsifiable concentrates, dispersants and water-dispersible granules. Dust formulations, soil application granules or granules for broadcasting and sprayable solutions generally do not require further dilution with other inert substances before application.
  • the application rate of the compound of formula (I) and/or its salt is influenced to some extent by external conditions such as temperature, humidity and the like.
  • the application rate can vary within a wide range.
  • the total amount of compounds of formula (I) and salts thereof 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 1kg/ha. This applies to pre-emergence and post-emergence applications.
  • the compounds of formula (I) and/or their salts are used as plant growth regulators, for example as for those crop plants as described above, exemplarily cereal plants (such as wheat, barley, Stem stabilizers for rye, triticale, millet, rice or maize) in total application rates of eg 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.
  • stem stabilizer can be carried out at various stages of plant growth. For example, after the tillering stage, at the beginning of longitudinal growth.
  • application as a plant growth regulator can also be by treating the seed, which includes various techniques for dressing and coating the seed.
  • the application rate depends on the specific technique and can be determined in preliminary tests.
  • the active compound that can be used in combination with the compound of formula (I) of the present disclosure in a composition of the present disclosure is, for example, based on inhibition of the following enzymes
  • Known active compounds such as: acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyl Phenylpyruvate 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 references cited therein.
  • known herbicides or plant growth regulators that can be combined with the compounds of the present disclosure are, for example, the active compounds that are known by the International Organization for Standardization (ISO) "common name" or their chemical name or its code representation. They generally include all use forms, eg acids, salts, esters and all isomeric (eg stereoisomers and optical isomers) forms, even if not explicitly mentioned.
  • ISO International Organization for Standardization
  • herbicides or plant growth regulators that can be used in combination with the compounds of formula I of the present disclosure are:
  • Lipid biosynthesis inhibitors selected from the group consisting of clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop , cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop-ethyl, fluazifop, fenoxaprop Fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop -methyl), haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, cyclosporine Ketone (profoxydim), propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop -P), quizalofop,
  • ALS inhibitors selected from the group consisting of bensulfuron, bispyribac, cinosulfuron, cloransulam, cloransulam-methyl , cyclosulfamuron, diclosulfuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron , Florasulam, Flucarbazone, Flucetosulfuron, Flumetulam, Flupyrsulfuron, Flupyrsulfuron-methyl -sodium), foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron sodium (iodosulfuron-methyl-sodium), mesosulfuron, metosulam, metsulfuron, metsulfuron-methyl, nicosulfuron, pyrimidine
  • Photosynthesis inhibitors selected from the group consisting of ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil ), bromofenoxim, bromoxynil and its salts and esters, chlorobromuron, chloridazone, cyanazine, desmedipham, Desmetryn, diquat-dibromide, diuron, fluometuron, hexazinone, ioxynil and their salts and esters, iso isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, paraquat (paraquat-dimetilsulfate), pentanochlor, phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil, extinguish Propazine, pyridafol, pyridate, siduron, simazine, simetry
  • Protoporphyrinogen-IX oxidase inhibitors selected from the group consisting of acifluorfen, aciflorfen-sodium, azafenidin, bencarbazone, diflufenazone (benzfendizone), bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, indofentrazone (cinidon-ethyl), fuazolate, fufenpyr, flufenpyr-ethyl, flumioxazin, fluoroglycofen ), fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, halosafen Lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profuazol (pyraclonil), pyraflufen, pyr,
  • Bleach herbicides selected from the group consisting of aclonifen, amitrol, beflubutamid, benzobicyclon, benzofenap, isofen Clomazone, diflufenican, fluridone, fluoxazone, flurochloridone, flurtamone, isoxaflutole, Mesotrione, norflurazon, picolinafen, pyrasulfutole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, bixlozone, sulfentrazone, cyclofenazone, sulfentrazone, 4-hydroxy-3-[[2-[(2-methoxyethoxy ) methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one (H-7; CAS 352010-68
  • EPSP synthase inhibitors selected from the group consisting of glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);
  • glutamine synthase inhibitors selected from the group consisting of: bilanaphos (bialaphos), bilanaphos-sodium, and glufosinate-ammonium;
  • DHP synthase inhibitors selected from the group consisting of: asulam;
  • Mitotic inhibitors selected from the group consisting of benfluralin, butralin, chlorpropham, dinitramine, dithiopyr, butalofen Ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, valprochlor (tebutam), thiazopyr and trifluralin;
  • VLCFA inhibitors selected from the group consisting of acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor ), dimethanamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet , metazachlor, metolachlor, S-metolachlor-S, naproanilide, napropamide, pethoxamid, Piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KIH-485) and thenylchlor );
  • cellulose biosynthesis inhibitors selected from the group consisting of chlorthiamid, dichlobenil, flupoxam and isoxaben;
  • auxin herbicides selected from the group consisting of 2,4-D and its salts and esters, 2,4-DB and its salts and esters, aminopyralid and its salts such as aminopyralid ammonium ( aminopyralid-tris(2-hydroxypropyl)ammonium) and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, two Clopyralid and its salts and esters, dicamba and its salts and esters, 2,4-D propionic acid (dichlorprop) and its salts and esters, homo 2,4-D propionic acid ( dichlorprop-P) and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, MCPA and its salts and esters, 2 methyl 4 chloroethyl thioester (MCPA-thioethyl), MCPB and its salts and esters
  • auxin transport inhibitors selected from the group consisting of diflufenzopyr, naptalam;
  • herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, Thatch, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, sodium methylarsine (DSMA), dymron, endothal ) and its salts, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, Flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, methyl- dymron), oxaziclomefone, pelargonic acid, pyributicarb, and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4- Pyridazinol (H-10);
  • the safener is benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenchlor fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, fenclorate, fenclorate, cyclopropanesulfonamide, 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).
  • Active compounds and safeners of groups b1)-b15) are known herbicides and safeners, see eg The Compendium of Pesticide Common Names; (http://www.alanwood.net/pesticides/); B. Hock, C .Fedtke, RR Schmidt, Herbizide [herbicide], Georg Thieme Verlag, Stuttgart, 1995.
  • Other herbicidal active compounds are described by WO 96/26202, WO 97/41116, WO 97/41117, WO 97/41118, WO 01/83459 and WO 2008/074991, W. et al. (eds.) "Modern CropProtection Compounds", Vol. 1, Wiley VCH, 2007 and references cited therein are known.
  • the compounds provided by the present disclosure have good activities for preventing and controlling harmful plants, and at the same time have good compatibility and effectiveness with crop plants, and have high-efficiency and broad-spectrum control of grass weeds, and at the same time have good effects on crop plants. compatibility.
  • the compounds or herbicidal compositions provided by the present disclosure have good control effects on barnyardgrass, foxtail, crabgrass, amaranth, etc., and can be used in wheat, soybean, rice, corn, orchard and non-arable land It can be used to control various malignant weeds.
  • control compound CK It is the compound disclosed in WO2016071364A2.
  • the present disclosure provides a compound with herbicidal activity, a herbicidal composition comprising the compound, and uses thereof, which have broad-spectrum herbicidal activity and have good control effects on barnyardgrass, foxtail, crabgrass, amaranth, etc. , can be used in wheat, soybeans, rice, corn, orchards and non-arable land to control various malignant weeds.

Abstract

La présente invention concerne un composé, une composition herbicide et une utilisation associée. Le composé comprend un composé tel que représenté par la formule (I), un N-oxyde du composé tel que représenté par la formule (I), et un sel du composé tel que représenté par la formule (I). Le composé ou la composition herbicide selon la présente invention a une activité herbicide à large spectre, a un bon effet de lutte contre le pied-de-coq, la sétaire verte, la digitaire sanguine, l'amaranthus retroflexus, etc, et peut être utilisé pour le blé, le soja, le riz, le maïs, le vergers, les terrains non cultivés, etc. pour lutter contre diverses mauvaises herbes malignes.
PCT/CN2021/102898 2020-07-15 2021-06-29 Composé, composition herbicide et utilisation associée WO2022012320A1 (fr)

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WO2016071364A2 (fr) * 2014-11-07 2016-05-12 Syngenta Participations Ag Composés herbicides
CN105636439A (zh) * 2013-10-07 2016-06-01 先正达参股股份有限公司 除草化合物
CN105658637A (zh) * 2013-10-25 2016-06-08 先正达参股股份有限公司 作为除草剂的吡啶基咪唑酮
CN113045548A (zh) * 2020-07-15 2021-06-29 周银平 一种化合物、除草组合物及其用途

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CN105636439A (zh) * 2013-10-07 2016-06-01 先正达参股股份有限公司 除草化合物
CN105658637A (zh) * 2013-10-25 2016-06-08 先正达参股股份有限公司 作为除草剂的吡啶基咪唑酮
WO2016071364A2 (fr) * 2014-11-07 2016-05-12 Syngenta Participations Ag Composés herbicides
CN113045548A (zh) * 2020-07-15 2021-06-29 周银平 一种化合物、除草组合物及其用途

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