CN113045548B - Compound, weeding composition and application thereof - Google Patents
Compound, weeding composition and application thereof Download PDFInfo
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- CN113045548B CN113045548B CN202010679811.4A CN202010679811A CN113045548B CN 113045548 B CN113045548 B CN 113045548B CN 202010679811 A CN202010679811 A CN 202010679811A CN 113045548 B CN113045548 B CN 113045548B
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- C07—ORGANIC CHEMISTRY
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- 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
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- 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
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Abstract
The invention provides a compound, a weeding composition and application thereof, wherein the compound comprises a compound shown as a general formula (I), an N-oxide of the compound shown as the general formula (I) and a salt of the compound shown as the general formula (I); the compound or the weeding composition has broad-spectrum weeding activity, has good control effect on barnyard grass, green bristlegrass, crab grass, redroot amaranth and the like, can be used for wheat, soybean, rice, corn, orchards, uncultivated areas and the like, and can be used for controlling various malignant weeds.
Description
Technical Field
The invention relates to the technical field of agricultural herbicides, and particularly relates to a compound, a weeding composition and application thereof.
Background
Substituted hydantoins with herbicidal properties can be described in a number of documents. Such as: WO2016071364A2, CN109790150A, CN105636439A, CN105658637A, WO2016/071361, WO2016/071362, WO2016/071363, WO2016/071364 and the like. However, these known compounds have inadequate herbicidal activity, in particular at low application rates, and/or their compatibility with crop plants is still worth improving.
The primary object of the present invention is to provide herbicidally active compounds (herbicides) which are very effective against economically important harmful plants even at relatively low application rates and can be used selectively on crop plants, and further which have good activity against harmful plants and at the same time have good compatibility with crop plants. Furthermore, these herbicidal compounds should be particularly effective and effective in controlling gramineous weeds in a broad spectrum and at the same time have good compatibility with crop plants.
Surprisingly, it has now been found that certain substituted triazinylimidazolone derivatives of formula (I) or salts thereof, as defined below, achieve this object and are particularly suitable as herbicides.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
A first object of the present invention is to provide a compound which has herbicidal activity and can be selectively used for crop plants, has good activity against harmful plants and at the same time has good compatibility with crop plants. The weeding composition is effective in removing weeds, can efficiently prevent and kill gramineous weeds in a broad spectrum, and has good compatibility with crop plants.
In order to achieve the above purpose of the present invention, the following technical solutions are adopted:
a compound comprising any one of a compound represented by the general formula (I), an N-oxide of the compound represented by the general formula (I), and a salt of the compound represented by the general formula (I);
wherein X is selected from O or S;
R1、R2identical or different and are respectively and independently selected from halogen, hydrogen, hydroxyl and C1-C6Alkylamino radical, halogeno C1-C6Alkylamino radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyloxy, halo C2-C6Alkynyloxy.
Preferably, in the general formula (I), X is O;
R1、R2the same or different and are each independently selected from: halogen, hydrogen, hydroxy, C1-C4Alkoxy, halo C1-C4An alkoxy group.
Preferably, in the general formula (I), X is O;
R1、R2the same or different and are respectively and independently selected from one of F, Cl, Br, I, H, hydroxyl, methoxy, ethoxy, propoxy, butoxy, trifluoromethoxy, trifluoroethoxy, difluoromethoxy or difluoroethoxy.
Preferably, in the general formula (I), X is O;
R1、R2the same or different, and are respectively and independently selected from one of F, Cl, Br, H, hydroxyl, methoxy, ethoxy, trifluoromethoxy or difluoromethoxy.
Preferably, in the general formula (I), X is O;
R1、R2the same or different, and are each independently selected from: cl, H, hydroxy, difluoromethoxy.
Preferably, the salt of the compound represented by the general formula (I) is selected from one of sodium salt, potassium salt, calcium salt and lithium salt of the compound represented by the general formula (I), and is preferably one of sodium salt, potassium salt and lithium salt.
A herbicidal composition comprising said compound as an active ingredient.
Preferably, the weight percentage of the compound in the weeding composition is 0.1-99%.
Preferably, the herbicidal composition further comprises a safener.
The use of said compounds or said herbicidal compositions for weed control.
Compared with the prior art, the invention has the beneficial effects that:
(1) the compound provided by the invention has good activity for preventing and removing harmful plants, has good compatibility with crop plants, is effective, can effectively prevent and remove gramineous weeds in a broad spectrum, and also has good compatibility with the crop plants.
(2) The compound or the weeding composition provided by the invention has good control effect on barnyard grass, green bristlegrass, crab grass, redroot amaranth and the like, can be used for wheat, soybean, rice, corn, orchards, uncultivated lands and the like, and can be used for controlling various malignant weeds.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following detailed description, but those skilled in the art will understand that the following described examples are some, not all, of the examples of the present invention, and are only used for illustrating the present invention, and should not be construed as limiting the scope of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The invention provides a compound, which comprises any one of a compound shown as a general formula (I), an N-oxide of the compound shown as the general formula (I) and a salt of the compound shown as the general formula (I);
in the formula:
x is selected from O or S;
R1、R2identical or different and are respectively and independently selected from halogen, hydrogen, hydroxyl and C1-C6Alkylamino radical, halogeno C1-C6Alkylamino radical, C1-C6Alkoxy, halo C1-C6Alkoxy radical, C1-C6Alkylthio, halo C1-C6Alkylthio radical, C2-C6Alkenyloxy, halogeno C2-C6Alkenyloxy radical, C2-C6Alkynyloxy, halo C2-C6Alkynyloxy.
In some preferred embodiments of the present invention, in the general formula (I), X is O;
R1、R2the same or different and are each independently selected from: halogen, hydrogen, hydroxy, C1-C4Alkoxy, halo C1-C4An alkoxy group.
In some preferred embodiments of the present invention, in the general formula (I), X is O;
R1、R2the same or different and are respectively and independently selected from one of F, Cl, Br, I, H, hydroxyl, methoxy, ethoxy, propoxy, butoxy, trifluoromethoxy, trifluoroethoxy, difluoromethoxy or difluoroethoxy.
In some preferred embodiments of the present invention, in the general formula (I), X is O;
R1、R2the same or different, and are respectively and independently selected from one of F, Cl, Br, H, hydroxyl, methoxy, ethoxy, trifluoromethoxy or difluoromethoxy.
In some preferred embodiments of the present invention, in the general formula (I), X is O;
R1、R2the same or different, and are each independently selected from: cl, H, hydroxy, difluoromethoxy.
In some preferred embodiments of the present invention, the salt of the compound represented by the general formula (I) is selected from one of sodium salt, potassium salt, calcium salt and lithium salt of the compound represented by the general formula (I), preferably one of sodium salt, potassium salt and lithium salt.
The invention provides a weeding composition which comprises the compound as an active component.
In some preferred embodiments of the present invention, the weight percentage of the compound in the herbicidal composition is 0.1% to 99%.
In some preferred embodiments of the present invention, the herbicidal composition further comprises a safener.
The invention also provides application of the compound or the weeding composition in weed control.
In the compounds of the present invention, tautomerism may be formed due to the presence of conjugated chemical bonds, and the present invention includes tautomers and mixtures thereof in any proportion.
In the definitions of the compounds of the general formula (I) given above, the terms used are generally defined as follows:
by substituted is meant that all substituents are hydrogen.
Halogen: refers to fluorine, chlorine, bromine or iodine.
Alkyl groups: straight-chain, branched or cyclic alkyl, such as methyl, ethyl, propyl, isopropyl, tert-butyl or cyclopropyl.
Halogenated alkyl groups: straight-chain or branched haloalkyl groups in which the hydrogen atoms may be partially or wholly replaced by halogen atoms, for example, haloalkyl groups such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl or trifluoromethyl.
Alkoxy groups: straight-chain, branched-chain or cyclic alkoxy, for example methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy or cyclopropoxy.
Haloalkoxy groups: straight-chain or branched haloalkoxy groups in which the hydrogen atoms may be partially or fully substituted by halogen atoms, for example, haloalkyl groups such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy or trifluoromethoxy groups.
Alkylthio group: straight or branched chain alkyl groups attached to the structure via a sulfur atom.
Haloalkylthio: straight-chain or branched alkylthio groups in which the hydrogen atoms may be partially or fully substituted by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like.
Alkenyl: straight-chain or branched and may have a double bond in any position, for example a vinyl or allyl group.
Alkynyl: straight or branched chain and may have a triple bond at any position, for example ethynyl or propargyl.
Bases which can form salts with the compounds represented by the general formula (I) of the present invention include: sodium hydroxide, potassium hydroxide, lithium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, lithium carbonate, and the like;
some of the compounds of the present invention can be illustrated by the specific compounds listed in Table 1, but are not intended to limit the present invention.
TABLE 1
The synthesis method comprises the following steps:
step one
The reaction is carried out in a suitable solvent selected from benzene, toluene, xylene, acetone, tetrahydrofuran, acetonitrile, N-dimethylformamide, N-methylpyrrolidone, dichloromethane, chloroform, dichloroethane, ethyl acetate, or the like. The reaction may 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 is accelerated. The base may be selected from alkali metal hydrides such as sodium hydride, lithium hydride or sodium amide, and the like; 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 may be between-10 ℃ and the boiling point of the solvent selected for the reaction, and is usually 0 to 100 ℃. The reaction time is 30 minutes to 20 hours, usually 1 to 10 hours.
Step two
The reaction is carried out in a suitable solvent selected from benzene, toluene, xylene, acetone, tetrahydrofuran, acetonitrile, N-dimethylformamide, N-methylpyrrolidone, dichloromethane, chloroform, dichloroethane, ethyl acetate, or the like. The reaction may 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 is accelerated. The base may be selected from alkali metal hydrides such as sodium hydride, lithium hydride or sodium amide, and the like; 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 may be between-10 ℃ and the boiling point of the solvent selected for the reaction, and is usually 0 to 100 ℃. The reaction time is 30 minutes to 20 hours, usually 1 to 10 hours.
The intermediates described herein are commercially available unless otherwise indicated.
The compounds of the general formula (I) and their agriculturally suitable salts are suitable for use as herbicides in the form of isomer mixtures and in the form of pure isomers. They are suitable for direct use or for use in suitably formulated compositions. Herbicidal compositions comprising compounds of the general formula (I) are very effective in controlling plant growth in non-crop areas, especially at high application rates. They act on broadleaf weeds and grassy weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop. This effect is mainly observed at low application rates.
The compounds of the invention of the general formula (I) and/or their salts are suitable for controlling monocotyledonous and dicotyledonous harmful plants of the following genera:
monocotyledonous harmful plants of the following genera: aegilops (aegiops), Agropyron (Agropyron), Agrostis (Agrostis), Alopecurus (Alopecurus), alexania (Apera), Avena (Avena), Brachiaria (Brachiaria), Bromus (broomus), tribulus (centhrus), Commelina (Commelina), bermuda (Cynodon), sedge (cypress), cogongrass (dactylotene), Digitaria (Digitaria), Echinochloa (Echinochloa), Eleocharis (elocharis), phacellus (Eleusine), setaria (setaria), setaria (Leptochloa), setaria (flagellata), setaria (Leptochloa), setaria (leptochloaria), setaria (leptochloaria), setaria) (leptochloaria), setaria) (leptochloaria), pinus (leptochloaria), setaria) (leptochloaria), pinipemia) (leptochloaria), pinus) (leptochloaria), pinus (leptochloaria), pinus) (leptochloaria), pinus) (leptochloaria), pinus (leptochloaria), pinus) (leptochloaria), pinus) (leptochloaria (paphio (leptochloaria), pinus) (leptochloaria (paphio), etc. (paphio (papyri), etc.), phacellaria), etc. (papyri), etc.), phaeocharosa) (paphio (papyri), etc.), phaeocharalis), etc. (papyri), etc.), phaeocharosa) (papyri (papyria), peltatus) (papyria) (papyri), etc.), phaeocharalis), etc. (papyria) (papyri (papyria), etc. (papyri), etc.), phaeocharalis), etc.), phae), etc. (papyri), etc.), papyri (papyri), skimmia (Scirpus), Setaria (Setaria), Sorghum (Sorghum).
Dicotyledonous harmful plants of the following genera: ambary (Abutilon), Amaranthus (Amaranthus), Ambrosia (Ambrosia), Malva (Andoa), Chamomilla (Anthemis), Aphanes (Aphanes), Artemisia (Artemisia), Atriplex (Atriplex), Bellis (Bellis), Bidens (Bidens), Capsella (Capsella), Carduus (Carduus), Cassia (Cassia), Centaurea (Centaurea), Chenopodium (Chenopodium), Cirsium (Cirsium), Convolvulus (Convolvulus), Gymnonia (Datura), Desmodium (Desmodium), Rumex (Emex), Brassica (Glycyrrhiza) (Euimum), Europe (Europium), weasel (Galeosoma), achyranthes (achyranthes), Galium (Galinoculus), Hibiscus (Ocimus), Mucora (Ochia), Pilus (Ocimum (Lecia), Pilus (Ocimum), Pilus (Ocimum (Lecia), Meristia), Pilus (Ocimum (Lepistia), Pilus (Pilus), Piper (Ocimum (Piper), Piper (Ocimum (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Piper (Piper), Pi, Poppy (Papaver), Pharbitis (Pharbitis), Plantago (Plantago), Polygonum (Polygonum), Portulaca (Portulaca), Ranunculus (Ranunculus), Raphanus (Raphanus), Rorippa (Rorippa), nodosa (Rotala), sorrel (Rumex), Salsola (Salsola), Senecio (seneco), Sesbania (Sesbania), Sida (Sida), Sinapis (Sinapis), Solanum (Solanum), endive (Sonchus), valvula (spinoclea), chickweed (stella), Taraxacum (taraxum), pennycress (Thlasi), clover (trillium), nettle (Urtica), Veronica (Vibrio), and violaxacum (Xanthola).
When the compound of the present invention is applied to the soil surface before the emergence of harmful plants (grasses and/or broadleaves) (pre-emergence method), seedlings of grasses and broadleaves can be completely prevented from emerging, or they can be allowed to grow until they reach the cotyledon stage, stop growing, and finally die completely after three to four weeks.
If the active compound is applied to the green parts of the plants after emergence, the growth is stopped after the treatment and the harmful plants remain in the growth phase at the point in time of application or die completely after a certain period of time, so that in this way the competition of weeds which are harmful to the crop plants is continuously eliminated at an extremely early point in time.
Although the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they cause damage to crop plants of economically important crops, for example dicotyledonous crops of the following genera, to only a small extent, or not at all, depending on the structure of the individual compounds according to the invention and their application rates: groundnut (Arachis), beetroot (Beta), Brassica (Brassica), Cucumis (Cucumis), Cucurbita (Cucurbita), Helianthus (Helianthus), Daucus (Daucus), Glycine (Glycine), Gossypium (Gossypium), Ipomoea (Ipomoea), Lactuca (Lactuca), Linum (Linum), Lycopersicon (Lycopersicon), Miscanthus (cisanthus), Nicotiana (Nicotiana), Phaseolus (Phaseolus), Pisum (Pisum), Solanum (Solanum), Vicia, or a monocotyledonous crop of the following genera: allium (Allium), Ananas (Ananas), Asparagus (Asparagus), Avena (Avena), Hordeum (Hordeum), Oryza (Oryza), Panicum (Panicum), Saccharum (Saccharum), Secale (Secale), Sorghum (Sorghum), triticale (triticale), triticum (triticum) and Zea (Zea). The compounds according to the invention are therefore very suitable for selectively controlling unwanted plant growth in crop plants, such as agriculturally useful plants or ornamental plants.
Furthermore, the compounds of the invention (depending on their specific structure and the application rate used) have excellent growth regulating properties on crop plants. They are involved in the metabolism of the plant itself with a regulatory action and can thus be used for the controlled influencing of plant constituents and for the promotion of harvesting, for example by triggering dehydration and stunting growth. Furthermore, they are suitable for the 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, as it may reduce or completely prevent lodging, for example.
Owing to their herbicidal and plant growth-regulating properties, the active compounds can also be used for controlling harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, transgenic plants are characterized by particularly advantageous properties, such as, for example, the expression of certain pesticides: in particular resistance to certain herbicides, to plant diseases or plant disease pathogens, such as certain insects or microorganisms (e.g. fungi, bacteria or viruses). Other specific properties relate to, for example, the quantity, quality, storage properties, composition and specific ingredients of the harvest. For example, transgenic plants with increased starch content or improved starch quality, or with harvests containing different fatty acid compositions are known. Other specific properties may be tolerance or resistance to abiotic stress factors, such as heat, cold, drought, salt and uv irradiation.
In view of the transgenic plants, it is preferred to use the compounds of the invention and/or their salts in economically important transgenic crops of useful plants and ornamentals, for example cereals (e.g.wheat, barley, rye, oats, millet, rice and maize) or other crops such as sugar beet, cotton, soybeans, rape, potatoes, tomatoes, peas and other vegetables.
The compounds of the formula (I) according to the invention or their salts are preferably used in economically important transgenic crops of useful plants and ornamentals, for example cereals (for example wheat, barley, rye, oats, triticale, millet, rice, cassava and maize) or other crops such as sugar beet, cotton, soybeans, oilseed rape, potatoes, tomatoes, peas and other vegetables.
The compounds of the formula (I) can preferably be used as herbicides for crops of useful plants which are resistant to the phytotoxic effects of the herbicide or for which said resistance has been obtained by recombinant techniques.
Conventional methods for making new plants with modified characteristics compared to existing plants include, for example, conventional breeding methods and the generation of mutants. Alternatively, new plants with altered characteristics can be produced by means of recombinant methods.
The compounds (I) according to the invention are preferably used in transgenic crops which are resistant to: growth regulators, such as dicamba (dicamba); or a herbicide that inhibits a plant essential enzyme such as acetolactate synthase (ALS), EPSP synthase, Glutamine Synthase (GS), or hydroxyphenylpyruvate dioxygenase (HPPD); or a herbicide selected from sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and similar active compounds.
When the active compounds according to the invention are used in transgenic crops, not only the effects on harmful plants observed in other crops, but also specific effects on the application to the particular transgenic crop, such as an altered or particularly broadened spectrum of the weeds which can be controlled, improved application rates which can be used for application, preferably good binding capacity with the herbicides to which the transgenic crop is resistant, and an influence on the growth and yield of the transgenic crop plants, frequently occur.
The present invention therefore also relates to the use of the compounds of the formula (I) according to the invention and/or their salts as herbicides for controlling harmful plants in crops of useful plants or ornamentals, optionally transgenic crop plants.
Preferably in cereals, preferably in maize, wheat, barley, rye, oats, millet or rice, by a pre-or post-emergence process.
Also preferred is the use in soybean by a pre-emergence or post-emergence method.
The use according to the invention for controlling harmful plants or for plant growth regulation also includes the case where the active compound of the formula (I) or a salt thereof is not formed from a precursor substance ("prodrug") until after application on plants, in plants or in the soil.
The present invention also provides the use of one or more compounds of the formula (I) or salts thereof or of the compositions of the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants, which comprises applying an effective amount of one or more compounds of the formula (I) or salts thereof to the plants (harmful plants, if appropriate together with the useful plants), to the plant seeds, to the soil in which the plants grow or to the soil or to the cultivation area.
The invention also provides a herbicidal and/or plant growth regulating composition, characterized in that it comprises
(a) One or more compounds of the formula (I) and/or salts thereof, as defined above, in each case as defined above,
and (b) one or more further substances selected from (i) and/or (ii):
(i) one or more further agrochemical active substances, preferably selected from insecticides, acaricides, nematicides, further herbicides (i.e. those which do not correspond to formula (I) defined above), fungicides, safeners, fertilizers and/or other growth regulators,
(ii) one or more formulation auxiliaries customary for crop protection.
The further agrochemical active substances of component (i) of The compositions of The invention are preferably selected from those mentioned in "The Pesticide Manual",16th edition, The British Crop Protection Council and The royal soc of Chemistry, 2012.
The herbicidal or plant growth regulating compositions according to the invention preferably comprise one, two, three or more formulation auxiliaries (ii) customary in crop protection, selected from surfactants, emulsifiers, dispersants, film-formers, thickeners, inorganic salts, dedusting agents, solid carriers at 25 ℃ and 1013 mbar, preferably adsorbent particulate inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably organic solvents miscible with water in any ratio at 25 ℃ and 1013 mbar.
The compounds (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in customary formulations. Accordingly, the present invention 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 salts thereof may 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, Suspension Concentrates (SC), oil-or water-based dispersions, oil-soluble solutions, Capsule Suspensions (CS), powders (DP), seed dressings, granules for broadcasting and soil application, granules in the form of microparticles (GR), spray granules, absorbent and adsorbent granules, water-dispersible granules (WG), water-Soluble Granules (SG), ULV formulations, microcapsules and waxes.
Wettable powders are preparations which can be uniformly dispersed in water and which, in addition to the active compound, contain diluents or inert substances, and also ionic surfactants and/or nonionic surfactants (wetting agents, dispersants), such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkylsulfonates, alkylbenzenesulfonates, sodium lignosulfonates, sodium 2,2 '-dinaphthylmethane-6, 6' -disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. To prepare wettable powders, the herbicidal active ingredients are finely ground, for example in conventional apparatus such as hammer mills, air mills and air jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.
The emulsifiable concentrate is prepared by the following process: the active compound is dissolved in an organic solvent (for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons) or a mixture of organic solvents, and one or more ionic and/or nonionic surfactants (emulsifiers) are added. Examples of useful emulsifiers are: calcium alkyl aryl sulfonates such as calcium dodecylbenzene sulfonate; or nonionic emulsifiers, for example fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensates, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.
Dusts can be obtained by grinding the active compound with finely divided solids, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspension concentrates may be water-based or oil-based. They can be prepared by wet milling, for example using a commercially available ball mill, and optionally adding surfactants such as those listed above in other dosage forms.
Emulsions, for example oil-in-water Emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents as listed above, for example in connection with the other dosage forms, and optionally surfactants.
Granules can be prepared by spraying the active compound on adsorbable, particulate inert substances or by coating the active compound concentrate on the surface of a carrier, for example sand, kaolin or particulate inert material, using binders, for example polyvinyl alcohol, sodium polyacrylate or mineral oil. Suitable active compounds can also be prepared as granules in the customary manner for preparing fertilizer granules, if desired mixed with fertilizers.
Water dispersible granules can generally be prepared by conventional methods such as spray drying, fluid bed granulation, pan granulation, mixing using high speed mixers and extrusion without solid inert substances.
The agrochemical, preferably herbicidal or plant growth-regulating compositions according to the invention preferably contain a total amount of from 0.1 to 99% by weight, preferably from 0.5 to 95% by weight, particularly preferably from 1 to 90% by weight, particularly preferably from 2 to 80% by weight, of active compounds of the formula (I) and salts thereof.
In wettable powders, the concentration of the active compound is, for example, from about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the concentration of active compound can be about 1 to 90% by weight, preferably 5 to 80% by weight. Formulations in powder form contain from 1 to 30% by weight of the active composition, generally preferably from 5 to 20% by weight of the active compound; the sprayable solution contains about 0.05 to 80% by weight, preferably 2 to 50% by weight, of the active compound. For water-dispersible granules, the active compound content depends in part on whether the active compound is in liquid or solid form, and on the granulation auxiliaries, fillers, etc. used. In the water-dispersible granules, the active compound is present, for example, in an amount of from 1 to 95% by weight, preferably from 10 to 80% by weight.
Furthermore, the active compound formulations mentioned optionally contain corresponding customary tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, antifoams, evaporation inhibitors and agents which influence the pH and viscosity. Examples of formulation auxiliaries are described, inter alia, in "Chemistry and Technology of agricultural Formulations", ed.D.A.Knowles, Kluwer Academic Publishers (1998).
The compounds of the formula (I) or their salts can be used as such or in the form of their formulations (preparations) in combination with other pesticidally active substances, for example insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example in the form of finished preparations or tank mixes. A combined preparation may be prepared based on the above-mentioned preparations while taking into consideration the physical properties and stability of the active compounds to be combined.
Active compounds which can be used in combination with the compounds of the formula (I) according to the invention in a mixture preparation or tank mix are, for example, known active compounds based on the inhibition of 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, for example, in Weed Research 26(1986)441-445or "The Pesticide Manual",16th edition, The British crop protection Council and The Royal Soc. of Chemistry,2012 and The references cited therein.
Of particular interest is the selective control of harmful plants in crops of useful plants and ornamental plants. Although the compounds (I) according to the invention are already very selective or even sufficiently selective in many crops, phytotoxicity to the crop plants can still occur in principle in some crops, in particular in mixtures with other herbicides of low selectivity. In this respect, compositions of the compounds (I) of the invention comprising compounds (I) or their compositions with other herbicides or pesticides and safeners are of particular interest. Safeners used in antidotally effective doses can reduce the phytotoxic side effects of herbicides/pesticides used, for example, in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, oilseed rape, cotton and soybeans, preferably 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 within wide ranges, for example from 200:1 to 1:200, preferably from 100:1 to 1:100, in particular from 20:1 to 1: 20. Similar to compound (I) or mixtures thereof, safeners can be formulated with other herbicides/pesticides and provided and used as finished preparations or as tank mixes with the herbicide.
For use, the herbicides or herbicide/safener formulations in the form commercially available are diluted in a conventional manner, if appropriate, for example with water in the case of wettable powders, emulsifiable concentrates, dispersants and water-dispersible granules. Dust formulations, soil-applied 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 a salt thereof is affected to some extent by external conditions such as temperature, humidity, and the like. Herein, the application rate may vary within a wide range. For application as herbicides for controlling harmful plants, the total amount of the compounds of the formula (I) and their salts is preferably from 0.001 to 10.0kg/ha, preferably from 0.005 to 5kg/ha, more preferably from 0.01 to 1.5kg/ha, in particular from 0.05 to 1 kg/ha. This applies to pre-and post-emergence applications.
When the compounds of the formula (I) and/or their salts are used as plant growth regulators, for example as stalk stabilizers for those crop plants, preferably cereal plants, as described above, such as wheat, barley, rye, triticale, millet, rice or maize, the total application rate is preferably from 0.001 to 2kg/ha, preferably from 0.005 to 1kg/ha, in particular from 10 to 500g/ha, very particularly from 20 to 250 g/ha. This applies to pre-and post-emergence applications.
Application as a stalk stabilizer may be carried out at various stages of plant growth. Preferably, it is applied, for example, after tillering, at the beginning of longitudinal growth.
Alternatively, application as a plant growth regulator may also be by treatment of the seed, which includes various techniques for dressing and coating the seed. Herein, the application rate depends on the particular technique and can be determined in preliminary tests.
Active compounds which can be used in combination with the compounds of the formula (I) according to the invention in the compositions according to the invention (for example in the form of mixed preparations or tank mixes) are, for example, known active compounds based on the inhibition of the following enzymes, 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-. Known herbicides or plant growth regulators which can be combined with the compounds of the invention are, for example, the active compounds indicated by the "common name" or by their chemical name or their code as specified by the international organization for standardization (ISO). They generally include all forms of use, such as acids, salts, esters, and all isomeric (e.g., stereoisomeric and optical isomeric) forms, even if not explicitly mentioned.
Examples of herbicides that can be used in combination with the compounds of formula I of the present invention are:
b1) a lipid biosynthesis inhibitor selected from the group consisting of: clethodim (clethodim), clodinafop (clodinafop), clodinafop-propargyl (clodinafop-propargyl), cycloxydim (cycloxydim), cyhalofop-butyl (cyhalofop-butyl), clomeprop (diclofop-methyl), prodiamine (diclofop-methyl), fenoxaprop-ethyl (fenoxaprop-ethyl), fluazifop-P (fluazifop-butyl), fluazifop-P (fluazifop-P), fluazifop-P (fluazifop-P-butyl), fluazifop-P (halofop-P), fluazifop (halofop-methyl), fluazifop (halofop-P), fluazifop (halofop-P-methyl), fluazifop (halofop-P (halofop), halofop (halofop-P), halofop (halofop), halofop (halofop-P (halofop-methyl), halofop (halofop-P-methyl), halofop-P (halofop), halofop (halofop-methyl), halofop (halofop-P (halofop-methyl), halofop-P-ethyl (halofop-P-butyl), halofop-P-methyl), halofop-P-ethyl (halofop-P-ethyl (halofop-methyl), halofop-ethyl (halofop-P-ethyl (halofop-methyl), halofop-P-butyl), halofop-ethyl (halofop-P-methyl), halofop-P-ethyl (halofop-methyl), halofop-P-ethyl (halofop-butyl), halofop-P-butyl), halofop-ethyl (halofop-P-ethyl (halofop-methyl), halofop-ethyl (halofop-P-ethyl (halofop-ethyl, halofop-ethyl (halofop-P-ethyl (halofop-ethyl, halofop-P-ethyl, halofop-P-methyl), halofop-P-ethyl (halofop-P-ethyl, halofop-P-ethyl, quizalofop-P, quizalofop-P-ethyl, tetrahydrofurfuryl, sethoxydim, and tralkoxydim.
b2) An ALS inhibitor selected from: bensulfuron-methyl (bensulfuron), pyrisulfuron-methyl (bispyribac), cinosulfuron (cinosulfuron), diclosulam (clavulan), pyrazosulfuron-ethyl (cloransulam), pyrazosulfuron-methyl (cloransulam-methyl), cyclosulfamuron (cyclosulfamuron), pyrazosulfuron-ethyl (diclosulam), ethametsulfuron (ethametsulfuron), ethametsulfuron-methyl (ethametsulfuron), sulfosulfuron (ethosulfuron), flazasulfuron (flumuron), fluorosulfuron (flucarbazone), flupyrazosulfuron (flusulfuron), fluazuron (fluxosulfuron), fluazifosulfuron (fluxosulfuron), sulfosulfuron (methyl-methyl), sulfosulfuron (methyl-methyl, sulfosulfuron (methyl), sulfosulfuron (methyl-methyl), sulfosulfuron (methyl-methyl, sulfosulfuron-methyl, sulfosulfuron (methyl-methyl, sulfosulfuron), sulfosulfuron (methyl, sulfosulfuron-methyl, sulfosulfuron (methyl, sulfosulfuron-methyl, methyl-methyl, sulfosulfuron-methyl, sulfosulfuron (methyl, methyl-methyl, methyl-methyl, sulfosulfuron-methyl, methyl-methyl, methyl-methyl, methyl-methyl, methyl-methyl, methyl-methyl, methyl-methyl, methyl-methyl, methyl-methyl, methyl-methyl, methyl-methyl, methyl-methyl, methyl, Sulfosulfuron (orthiosulfuron), thifensulfuron (oxasulfuron), penoxsulam (penoxsulam), primisulfuron (primisulfuron-methyl), tribenuron (propoxycarbazone-sodium), prosulfuron (prosulfuron), pyrazosulfuron (pyrazosulfuron-ethyl), pyrithiobac (pyrithiobac), pyriftalid (pyriftalid), pyribenzoxim (pyriminobac-methyl), pyrithiobac (pyriftalid), thifensulfuron (thifenuron), thifensulfuron (thifensulfuron), thifensulfuron-methyl), pyribenzoxim (pyrifensulfuron-methyl), pyribenzoxim (pyribenzoxim-methyl), pyribenzoxim (trifloxysulfuron-methyl), trifloxysulfuron (triflusulfuron-methyl), triflusulfuron (triflusulfuron), triflusulfuron (triflusulfuron-methyl), triflusulfuron (triflusulfuron), triflusulfuron-methyl), triflusulfuron (triflusulfuron-methyl), triflusulfuron (triflusulfuron), triflusmethyl), triflusulfuron (triflusmethyl), triflusulfuron (triflusmethyl), triflusulfuron-methyl), triflusulfuron (triflusmethyl), triflusulfuron (triflusulfuron-methyl), thifensulfuron-methyl), thiuron (triflusmethyl), thifensulfuron-methyl) and triflusmethyl); (imazamethabenz z), imazamethabenz-methyl, imazamox (imazamox), imazapic (imazapic), imazapyr (imazapyr), imazaquin (imazaquin), imazethapyr (imazethapyr), mazosulfuron (imazosulfuron), iodosulfuron (iodosulfuron), iodosulfuron-methyl-sodium (iodosulfuron-methyl-sodium), mesosulfuron (mesosulfuron), imazasulfuron (metosulsulfuron), metsulfuron-methyl, metsulfuron (nicosulfuron), sulfosulfuron (metosulron), thifensulfuron (metosuluron), thifensulfuron (oxypuron), pyrisulfuron (oxypyrisulfuron), pyrisulfuron (oxasulfuron), pyrisulfuron (penoxsulam), pyrisulfuron (pyrifos (penoxsulsulfuron), pyrifos (pyrifos-methyl), pyrisulfuron (pyrifos), pyrifos (pyrifos-methyl), pyrisulfuron-methyl (pyrifos), pyrifos (pyrifos-methyl, pyrifos (pyrifos), pyrifos (pyrifos-methyl, pyrifos (pyrifos), pyrifos-methyl, pyrifos (pyrifos-methyl, pyrifos) and pyrifos (pyrifos) as.
b3) A photosynthesis inhibitor selected from the group consisting of: ametryn (ametryn), amicarbazone (amicarbazone), atrazine (atrazine), bentazone (bentazone-sodium), bromacil (bromoacil), desmetrofloxacin (bromoxynil) and salts and esters thereof, chlorsulfuron (chlorobromouron), chlorfenapyr (chlordizazone), cyanazine (cyanazine), fentrazone (cyazone), isopyrazine (desmediphazone), dimethenan (desmetryn), diquat-dibromide (diumuron), diuron (diuron), fluometuron (fluometuron), hexazinone (hexazinone), ioxynil (ioxynil) and salts and esters thereof, isoproturon (isoproturon), pyributhiuron (prophyridone), pyributhiuron (pyributhiuron), pyributhiuron (bentazone), pyributhiuron (bentazone (pyributhiuron), pyributhizim (pyributron), pyributron (pyrim), pyribencarb (pyrim (bencarb), pyribencarb (bencarb), pyribencarb (bencarb), pyribencarb (bencarb), pyribencarb (bencarb), pyribencarb (bencarb), pyribencarb (bencarb), pyrim (bencarb), pyribencarb), pyrim (bencarb), pyribencarb (bencarb), pyribencarb (bencarb), pyrim (bencarb), pyribencarb (bencarb), pyrim (bencarb), pyribencarb (bencarb), pyribencarb (bencarb, pyridafol, pyridate (pyritre), siduron (siduron), simazine (simazine), simetryn (simetryn), terfenadine (terbacil), terbuthylazine (terbutyrazine).
b4) A protoporphyrinogen-IX oxidase inhibitor selected from the group consisting of: acifluorfen (acifluorfen), acifluorfen-sodium (acifluorfen-sodium), fenpropidin (azafenidin), bencarbzone, benfenazone (benfendizone), bifenox (bifenox), butafenacil (butafenacil), carfentrazone-ethyl), chlorfenapyr (chlorfenapyr), indolofen (cinidon-ethyl), isoxaflufen (furazolate), flupyridazinyl (furfenpyr), flupyridazinyl (fenpyr-ethyl), fluoroxafen (fluorofenpyr-ethyl), fluorooxazone (fluoroxazin (flufenpyr), fluoroglycofen (fluoroglycofen-ethyl), fluorofenofen (fluorofenpyr-ethyl), fluorofenoxafen (fluorofen-ethyl), fluorofenoxafen (fluorofen-ethyl), fluorofenoxafen (fluorofen-ethyl), fluorofenoxafen (fluorofenoxafen-ethyl), fluorofenoxafen-ethyl (fluorofenoxafen-ethyl), fluorofenoxafen (fluorofenoxafen-ethyl), fluorofenoxafen-ethyl (fluorofenoxafen-ethyl), fluorofenoxafen-ethyl (fluorofenoxafen-ethyl), fluorofenoxafen-ethyl (fluorofenoxafen-ethyl), fluorofenoxafen-ethyl (fluorofenoxaprop-ethyl), fluorofenoxaprop-ethyl (fluorofenoxaprop-ethyl), fenoxaprop-ethyl (fluorofenoxaprop-ethyl, fluorofenoxaprop-ethyl (fluorofen-ethyl), flufen-ethyl), fluorofenoxaprop-ethyl, flufen-ethyl (fluorofenoxaprop-ethyl), flufen-ethyl), fluorofen-ethyl, flufen-ethyl), flufen-ethyl (fluorofen-ethyl, flufen-ethyl, flu, Pyraflufen-ethyl (pyraflufen-ethyl), saflufenacil (saflufenacil).
b5) A bleach herbicide selected from the group consisting of: aclonifen (aclonifen), mefenapyr (amitrol), beflubutamid (beflubutamid), benzobicyclon (benzobicyclon), benzofenap (benzofenap), clomazone (clomazone), diflufenican (diflufenican), fluroxypyr (flurididone), fluridone, flurtamone (flurochlorodinone), flurtamone (flurtamone), isoxaflutole (isoxaflutole), mesotrione (mesotrione), norflurazon (norflurazon), flupyrazamide (picolinafen), pylfuron, pyrazolate (pyrazynate), pyrazoxazole (pyrazoxyn), sulcotrione (pyroxyzone), sulcotrione (sultoprione), tefuryltrione, tembotrione, benzofenazone (pyraclostrobin), pyrazoxyzone (pyrazoxyzone), pyrazoxyzone (3-2-3-benzoxyzone, 3-2-3-4-ethoxybenzoxazone, 3-2-3-2, 3-2, 4, 3, 4, 3, 2,3, 2,3, 2,3, 2,3, 2,3, 2,3, 2,3, 2,3, 2,3 -2- (4-trifluoromethylphenyl) pyrimidine (H-8; CAS 180608-33-7);
b6) an EPSP synthase inhibitor selected from: glyphosate, glyphosate isopropylamine (glyphosate-isopyrammonium) and phosphinothricin (glyphosate-trimetium) (sulfosate);
b7) a glutamine synthetase inhibitor selected from: bialaphos (bialaphos), bialaphos-sodium, glufosinate-ammonium;
b8) a DHP synthase inhibitor selected from the group consisting of: asulam (asulam);
b9) a mitotic inhibitor selected from the group consisting of: flufenacet (benfluralin), dimethomorph (butralin), chlorpropham (chlorpropham), dinoamine (dinitramine), dithiopyr (dithiopyr), ethalfluralin (ethalfluralin), flufenacet (fluchlalin), oryzalin (oryzalin), pendimethalin (pendimethalin), prodiamine (prodiamine), prodiamine (propham), naproxen (propyzam), naphalon (propyzamide), tebufam (tebutham), thifluzamide (thiazopyr), and trifluralin (trifluralin);
b10) a VLCFA inhibitor selected from: acetochlor (acetochlor), alachlor (alachlor), anilofos (anilofos), butachlor (butachlor), cafenstrole (cafenstrole), pretilachlor (dimethachlor), dimethenamid (dimethanamid), dimethenamid-P, metamifop (diaphenamid), fentrazamide (fentrazamide), flufenacet (flufenacet), mefenacet (mefenacet), metazachlor (metazachlor), metolachlor (metolachlor), S-metolachlor (metolachlor), napropamide (naproxamide), naproxen (naproxamide), pethoxamid (pethofos), propinophos (pretiassociated), propisochlor (propachlor), propachlor (propachlor), isopropamide (propachlor), propachlor (propachlor), thiflufenamide (thiobenethofen) (H-P-methyl ether (propachlor);
b11) a cellulose biosynthesis inhibitor selected from the group consisting of: chloramber (chlorethaamid), dichlobenil (dichlobenil), fenchlorazole (flupoxam) and isoxachlor (isoxaben);
b12) an herbicide isolate selected from the group consisting of: dinotefuran (dinoseb), dinotefuran (dinoterb) and Dinitrocresol (DNOC) and salts thereof;
b13) an auxin herbicide selected from the group consisting of: 2,4-D and salts and esters thereof, 2,4-DB and salts and esters thereof, triamcinolone (aminopyralid) and salts thereof such as ammoniumsulfate-tris (2-hydroxypropyl) ammonium and esters thereof, benazolin (benazolin), benazolin (benazolin-ethyl), clomiphene (chloriumben) and salts and esters thereof, clomeprop (clomeprop), clopyralid (cyclopyralid) and salts and esters thereof, dicamba (dicamba) and salts and esters thereof, 2, 4-dichloropropion (dichlorprop) and salts and esters thereof, dichloropropion (dichloroprop) and salts and esters thereof, dichloropropyl (dichloropropyl) and salts and esters thereof, fluroxypyr-butoxypyr, dichloropropyl (dichloropropyl), MCPCMCMP and salts and esters thereof, MCP (MCP) and salts and esters thereof, MCP (2, 4-chloromethyl) and salts and esters thereof, fluroxypyr, MCP (2, 4-methyl chloride) and salts and esters thereof, MCP (MCP) and salts and esters thereof, MCP (chlorambup, and salts and esters thereof, BPA, and MCP (chlorambup) and salts and esters thereof, benazolin, benazolidin (benazolin, and salts and esters thereof, benazolidin (benazolidin ester thereof, and salts thereof, and salts thereof, wherein MCP, and salts thereof, and salts of fluroxypyr, Picloram (picloram and its salts and esters, quinclorac), quinmerac (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 (H-9; b14) auxin transport inhibitors selected from the group consisting of diflufenzopyr and bentazone (naptalam);
b15) other herbicides selected from the group consisting of: bromobutyroletamide (bromobutide), chlordane (chlorflunol), chlordane (chlorflubenz-methyl), cinmethylin (cinmethylin), cumyluron (cumyluron), dalapon (dazomet), dichloflubenz (difenon), dichlorbenz (difenon-methyl), dichlorbenz (dichlorbenz-methyl), thionine (dimethipin), meconium sodium (DSMA), vanillyl (dyron), dichlobenil (endothal) and its salt, flufenapyr (flumprop), flufenapyr (flufenop-M-isopropyl), dicamba (flufenop-M-methyl), butazone-butyl (dyflurenol), flufenapyr (flufenapyr-butyl), pyrimethan (flupyrimethanil), pyrimethan (ammonium chloride), pyributron (ben-methyl), pyributron (bengal (2-methyl), pyributron (pyributron-methyl), pyributron (pyrithiobac (2-methyl-ethyl), pyrithiobac (pyrimethan-methyl-2-ben (pyrine-methyl-2-ethyl), pyrimethan-methyl-ben (pyrimethan-methyl-2-methyl-ben-methyl-ben-methyl-2-ben-methyl-ben-methyl-ben-methyl-ben, ben-methyl, ben-methyl-ben-methyl-ben-methyl-ben-methyl-ben-methyl-ben (ben-methyl-ben-methyl-ben-methyl-ben-methyl-ben-methyl-ben-methyl-ben-methyl-ben-methyl-ben-methyl-ben-methyl ben-methyl-ben (ben-methyl-ben-methyl-ben-methyl (ii) a
Preferred safeners are benoxacor (benoxacor), cloquintocet (cloquintocet), chlorfenapyr (cyclotrinil), cyprosulfamide, chlorfenapyr (dichlormid), dicyclonone, dietholate, fenchlorazole (fenchlorazole), fenclorim (fenclorim), fenclozole (fluxazole), fluxofenam (fluxofenam), flurazon (furilazole), isoxadifen (isoxadifen), cloquinate, mefenpyr, cyprosulfamide, pyrric acid (menpyr), mephenate, naphthalic anhydride (naphthalic anhydride), oxabetrinil (oxabetrinil), 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (H-11; MON4660, CAS 71526-07-3) and 2, 2-5-acetyl-5- (CAS 523, 5-trimethyl-L-12; CAS 5231, R-31, R-29148).
b1) -b15) are known herbicides and safeners, see for example The complex of Pesticide Common Names; (http:// www.alanwood.net/pestides /);
hock, c.fedtke, r.r.schmidt, Herbizide [ herbicides ], Georg Thieme Verlag, Stuttgart, 1995. Further herbicidally active compounds are known from WO96/26202, 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 references cited therein.
The compounds of the formula I are illustrated below by way of examples, without the subject matter of the invention being restricted to the examples shown.
Embodiments of the present invention will be described in detail below with reference to examples, but it will be understood by those skilled in the art that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products commercially available.
Example 1
This example relates to the preparation of compound 21 in table 1:
3.7 g of 2,4, 6-trichloro-1, 3, 5-triazine (0.02mol), 2.3 g of 1-methylhydantoin (0.02mol), 3 g of triethylamine (0.029mol) and 80ml of acetonitrile are added to a 250ml four-neck flask, the temperature is raised to 60 ℃, the reaction is stirred for 1 hour, after the reaction is finished, the solvent is removed, and 100ml of water is added. Extraction was carried out with 100ml of ethyl acetate. The product is obtained by column chromatography 5.2 g. A sticky substance. Δ ppm 4.21(2H, s), 3.22(3H, s).
Example 2
This example relates to the preparation of compound 2 in table 1:
2.6 g of compound 21(0.01mol), 3 g of potassium carbonate (0.021mol), 80ml of acetonitrile and 20 g of water are added into a 250ml four-neck flask, the temperature is raised to 60 ℃, the reaction is stirred for 3 hours, after the reaction is finished, the solvent is removed, 50ml of water is added, and the pH value is adjusted to about 5 by hydrochloric acid. Extraction was carried out with 100ml of ethyl acetate. The product is obtained by column chromatography with a melting point of 120-122 ℃. Δ ppm 4.09(2H, s), 3.09(3H, s).
Example 3
This example relates to the preparation of compound 9 in table 1:
2.25 g of compound 2(0.01mol), 0.8 g of sodium hydroxide (0.02mol) and 60 g of methanol are added into a 250ml four-neck flask at room temperature, stirred and reacted for 1 hour at room temperature, and the solvent is removed under reduced pressure to obtain 2.9 g of a product. Melting point 280-. Δ ppm 3.92(2H, s), 2.97(3H, s).
Example 4
This example relates to the preparation of compound 18 in table 1:
2.25 g of Compound 2(0.01mol), 2 g of anhydrous potassium carbonate (0.014mol) and 80ml of anhydrous acetonitrile were charged in a 250ml four-necked flask, and difluoromethane was introduced thereinto, and the reaction was stirred at room temperature for 3 hours, after completion of the reaction, the solvent was removed, 100ml of water was added, and extraction was carried out with 100ml of ethyl acetate. The column chromatography gave 1.86 g. Delta ppm 7.48-7.52(2H, t), 4.18(2H, s), 3.16(3H, s).
Herbicidal action before emergence of seedlings
Seeds of monocotyledonous and dicotyledonous weed plants or crop plants are placed in sandy loam in a lignocellulosic pot and covered with soil. The formulated compound of general formula (I) according to the invention is then sprayed in the form of an aqueous suspension or emulsion (0.2% of wetting agent added) over the surface of the soil at an application rate of 600 litres of water per hectare (converted). After treatment, the pots were placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect was assessed visually (in percent) by comparison with untreated controls. For example, 100% activity is when the plant has died, 50% herbicidal activity or damage is when the plant is reduced to 50% or when the plant material is reduced by 50%, 0% activity is similar to the control plant.
Table 2 pre-emergence herbicidal action of the compounds of general formula (I) according to the invention: (dosage: 300g/ha)
| Numbering | Barnyard grass | Tang style food | Snakehead sausage | Amaranthus retroflexus (lour.) Merr | Root of shredded cyperus | Herb of common Setaria | Corn (corn) |
| 2 | 92.8 | 90.5 | 88.2 | 87.9 | 85.9 | 95.4 | 0 |
| 7 | 88.4 | 90.3 | 85.4 | 84.5 | 88.6 | 86.7 | 0 |
| 9 | 93.4 | 92.3 | 84.2 | 83.6 | 82.1 | 96.2 | 0 |
| 18 | 86.4 | 88.6 | 80.2 | 89.6 | 89.2 | 88.4 | 0 |
| CK | 45.3 | 48.2 | 48.3 | 36.8 | 48.7 | 46.8 | 10 |
Control Compound CK
Compounds are disclosed in WO2016071364a 2.
Compounds are disclosed in WO2016071364a 2.
Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are placed in sandy loam in lignocellulosic 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 one-leaf stage and sprayed with the compound of the general formula (I) according to the invention formulated in the form of an aqueous suspension or emulsion (0.2% of wetting agent added) at an application rate of 600 l of water per hectare (converted) onto the green parts of the plants. The activity of the formulations was then assessed visually (in percent) by comparison with untreated controls after the test plants had been placed in the greenhouse for about 3 weeks under optimal growth conditions. For example, 100% activity is dead, 50% herbicidal activity or damage is reduced to 50% or plant material is reduced by 50%, 0% activity is similar to control plants.
Table 3 post-emergence herbicidal action of the compounds of the general formula (I) according to the invention: (dosage: 300g/ha)
| Numbering | Barnyard grass | Tang style food | Snakehead sausage | Amaranthus retroflexus (lour.) Merr | Root of shredded cyperus | Herb of common Setaria | Corn (corn) |
| 2 | 88.7 | 100 | 95.8 | 100 | 92.7 | 100 | 0 |
| 7 | 92.4 | 100 | 96.5 | 100 | 98.3 | 100 | 0 |
| 9 | 90.4 | 98.2 | 94.3 | 100 | 90.2 | 100 | 0 |
| 18 | 91.2 | 94.5 | 92.8 | 97.6 | 96.3 | 100 | 0 |
| CK | 48.3 | 41.5 | 46.4 | 48.3 | 50.8 | 42.4 | 12 |
As can be seen from tables 2 and 3, compared with the control, the herbicidal activity of the compound of the invention is far superior to that of the control compound no matter the soil before seedling treatment or the stem and leaf treatment after seedling; meanwhile, compared with a control compound, the compound provided by the invention has better safety to corn.
While particular embodiments of the present invention have been illustrated and described, it will be appreciated that the above embodiments are merely illustrative of the technical solution of the present invention and are not restrictive; those of ordinary skill in the art will understand that: modifications may be made to the above-described embodiments, or equivalents may be substituted for some or all of the features thereof without departing from the spirit and scope of the present invention; the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention; it is therefore intended to cover in the appended claims all such alternatives and modifications that are within the scope of the invention.
Claims (9)
1. A compound characterized by comprising any one of a compound represented by the general formula (I) and a salt of the compound represented by the general formula (I);
wherein X is O or S;
R1、R2the same or different and are respectively and independently selected from hydroxyl and trifluoroOne of methoxy, trifluoroethoxy, difluoromethoxy or difluoroethoxy.
2. The compound of claim 1, wherein in the formula (I), X is O;
R1、R2the same or different, and are respectively and independently selected from one of hydroxyl, trifluoromethoxy or difluoromethoxy.
3. The compound of claim 1, wherein in the formula (I), X is O;
R1、R2the same or different, and are each independently selected from: hydroxy, difluoromethoxy.
4. A compound according to any one of claims 1 to 3, wherein the salt of the compound of formula (I) is selected from one of the sodium, potassium, calcium and lithium salts of the compound of formula (I).
5. The compound of claim 4, wherein the salt of the compound of formula (I) is selected from the group consisting of sodium, potassium and lithium salts of the compound of formula (I).
6. A herbicidal composition comprising the compound of any one of claims 1 to 5 as an active ingredient.
7. The herbicidal composition as claimed in claim 6, wherein the mass percentage of the compound in the herbicidal composition is 0.1% to 99%.
8. A herbicidal composition according to claim 6, characterized in that it further comprises a safener.
9. Use of a compound according to any one of claims 1 to 5or a herbicidal composition according to any one of claims 6 to 8 for the control of weeds, wherein the species of weeds comprise barnyard grass, large crabgrass, eclipta prostrata, amaranthus retroflexus, cyperus rotundus, setaria viridis.
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| PCT/CN2021/102898 WO2022012320A1 (en) | 2020-07-15 | 2021-06-29 | Compound, herbicidal composition, and application thereof |
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| WO2016071364A2 (en) * | 2014-11-07 | 2016-05-12 | Syngenta Participations Ag | Herbicidal compounds |
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| GB201318863D0 (en) * | 2013-10-25 | 2013-12-11 | Syngenta Ltd | Herbicidal compounds |
| CN113045548B (en) * | 2020-07-15 | 2022-01-28 | 周银平 | Compound, weeding composition and application thereof |
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| CN112745305A (en) * | 2019-10-29 | 2021-05-04 | 沈阳中化农药化工研发有限公司 | Triazinone compound and application thereof |
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