WO2025209889A1 - Compositions herbicides - Google Patents
Compositions herbicidesInfo
- Publication number
- WO2025209889A1 WO2025209889A1 PCT/EP2025/058160 EP2025058160W WO2025209889A1 WO 2025209889 A1 WO2025209889 A1 WO 2025209889A1 EP 2025058160 W EP2025058160 W EP 2025058160W WO 2025209889 A1 WO2025209889 A1 WO 2025209889A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- plants
- herbicides
- combination
- total amount
- resistance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
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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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
Definitions
- Some weeds have developed almost complete tolerance to herbicides of a certain Mode of Action, that is, they are virtually undamaged by these herbicides at the normal commercial application rates. Sometimes the word “resistant” is also used to describe such weeds, in particular where they have the inherited ability to survive treatment by these herbicides.
- the active ingredient diflufenican (IUPAC name: 2',4'-difluoro-2-[3- (trifluoromethyl)phenoxy]pyridine-3-carboxanilide) is an active herbicidal ingredient (herbicide) known from US 4,618,366.
- Diflufenican controls unwanted weed plants pre-emergence and early postemergence in certain crops; see, for example, "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012, p. 355-357.
- Diflufenican is an inhibitor of the phytoene desaturase (PDS), blocking carotenoid biosynthesis.
- the active ingredient mesotrione (IUPAC name: 2- [4- (methylsulfonyl) -2- nitrobenzoyl] cyclohexane - 1, 3-dione) is an active herbicidal ingredient (herbicide) known from US 5,006,158, US 5,506,195 and US 5,912,207.
- mesotrione controls unwanted weed plants in certain crops; see, for example, "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012, p. 728-729.
- Mesotrione is an inhibitor of the 4-hydroxyphenylpyruvate dioxygenase (HPPD).
- Herbicidal combinations often extend the weed spectrum for control relative to each of the individual active ingredients, but without producing further possibilities for use, such as deployment in other crops of useful plants, or shifting of the application window.
- these herbicidal combinations known from the prior art do not (sufficiently) solve the problem of evolving or increasing resistance developed by weed plants (weeds) to active herbicidal ingredients from certain Modes of Action, for example HPPD inhibitors such as mesotrione.
- Example embodiments of the present disclosure are generally directed to herbicidal combinations comprising: (A) rimisoxafen and (B) diflufenican (e.g., as active herbicidal ingredients, etc.).
- Example embodiments of the present disclosure are also generally directed to herbicidal combinations comprising (A) rimisoxafen, and (B) diflufenican and (C) mesotrione.
- Example embodiments of the present disclosure are also generally directed to methods for controlling weed plants in crops of useful plants, for example, by applying one or more of the herbicidal combinations described above (and/or otherwise described herein) to the weed plants, plants, plant seeds, or to the area on which the weed plants are or will be growing. Further areas of applicability will become apparent from the description provided herein. The description and specific examples in this summary are intended for purposes of illustration only and are not intended to limit the scope of the present disclosure.
- herbicidal combinations or compositions wherein the active herbicidal ingredients comprise or consist of (A) rimisoxafen, and (B) diflufenican and (C) mesotrione.
- rimisoxafen component (A)
- diflufenican B
- diflufenican B
- mesotrione B
- C mesotrione
- the herbicidal combination or composition according to the present disclosure contains as sole active herbicidal ingredients (A) rimisoxafen, and (B) diflufenican; wherein the ratio by weight of the total amount of component (A) to the total amount of component (B) is in the range of from about 10 : 1 to about 1 : 10.
- the ratio by weight of the total amount of component (A) to the total amount of component (B) is in the range of from about 4 : 1 to about 1 : 4.
- the herbicidal combination or composition according to the present disclosure contains as sole active herbicidal ingredients (A) rimisoxafen, and (B) diflufenican and (C) mesotrione; wherein the ratio by weight of the total amount of component (A) to the combined total amount of component (B) and (C) is in the range of from about 10 : 1 to about 1 : 10.
- the ratio by weight of the total amount of component (A) to the combined total amount of component (B) and (C) is in the range of from about 4 : 1 to about 1 : 4.
- the herbicidal combination or composition according to the present disclosure preferably is a composition (i.e. a mixture), preferably in the form of a concentrated formulation or a ready-to-use diluted spray application mixture (tank-mix).
- the herbicidal combinations or compositions of the disclosure may comprise or else be used together with additional, further components, examples being active crop protection ingredients of other kinds and/or adjuvants customary in crop protection and/or formulating assistants.
- the combinations and compositions according to the present disclosure may be combined with one or more further herbicides.
- Safeners and further herbicides optionally incorporated into the herbicidal combinations and compositions of the present disclosure and the common names used herein are known in the art; see, for example, "The Pesticide Manual” 16th Edition, British Crop Protection Council 2012; these include the known stereoisomers (in particular racemic and enantiomeric pure isomers) and derivatives such as salts or esters, and particularly the commercially customary forms.
- a herbicide is referenced generically herein by name, unless otherwise restricted, that herbicide includes all commercially available forms known in the art such as salts, esters, free acids and free bases, as well as stereoisomers thereof.
- glyphosate glyphosate acid, salts and esters are within the scope thereof.
- the one or more further herbicides can be selected from the group consisting of acetyl CoA carboxylase (ACCase) inhibitors, enolpyruvyl shikimate-3 -phosphate synthase (EPSPS) inhibitors, glutamine synthetase inhibitors, auxins, photosystem I (PS I) inhibitors, photosystem II (PS II) inhibitors, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, 4- hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, cellulose inhibitors, mitosis inhibitors, oxidative phosphorylation uncouplers, dihydropteroate synthase inhibitors, very long chain fatty acid inhibitors and fatty acid thioesterase inhibitors and lipid biosynthesis inhibitors, auxin transport inhibitors and carotenoid biosynthesis inhibitors,
- the additional herbicides with which the herbicidal combinations or compositions according to the present disclosure may be combined or mixed are preferably selected from the group consisting of herbicides from WSSA Group 4 (auxin herbicides), WSSA Group 14 (protoporphyrinogen oxidase (PPG) inhibitor herbicides) and WSSA Group 15 (VLCFA inhibitor herbicides).
- the auxin herbicide comprises dicamba and/or a salt thereof.
- dicamba salts include the monoethanolamine, tetrabutylamine, dimethylamine (e.g., BANVEL, ORACLE, etc.), isopropylamine, diglycolamine (e.g., CLARITY, VANQUISH, etc.), potassium, and sodium salts, and combinations thereof.
- Commercially available sources of dicamba and its salts includes those products sold under the trade names BANVEL, CLARITY, DIABLO, DISTINCT, ORACLE, VANQUISH, and VISION.
- the auxin herbicide component comprises 2,4-D and/or a salt thereof.
- 2,4-D salts include the choline, dimethylamine, and isopropylamine salts, and combinations thereof.
- Commercially available sources of 2,4-D and its salts include those products sold under trade names BARRAGE, FORMULA 40, OPT- AMINE, and WEED AR 64.
- Herbicides from WSSA Group 14 are protoporphyrinogen oxidase (PPO) inhibitor herbicides suitable to be combined with combinations and compositions according to the present disclosure include, for example, acifluorfen, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone-ethyl, chlomethoxyfen, chlomitrofen, cinidon-ethyl, ethoxyfen-ethyl, epyrifenacil (ethyl [3-[2-chloro-4-fluoro- 5-(l-methyl-6-trifluoromethyl-2,4- dioxo- 1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2- pyridyloxy] acetate), fluazolate, flufenpyr-ethyl, flufenoximacil, flumiclorac, flumiclorac -pentyl
- Herbicides from WSSA Group 15 are very long-chain fatty acid (VLCFA) synthesis inhibitor herbicides suitable to be combined with combinations and compositions according to the present disclosure include, for example, acetochlor, alachlor, butachlor, butenachlor, delachlor, diethatyl, dimethachlor, dimethenamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, napropamide, naproanilide, pethoxamid, pretilachlor, pronamide, propachlor, propisochlor, prynachlor, terbuchlor, thenylchlor and xylachlor, agriculturally acceptable salts and esters thereof, and mixtures thereof.
- the herbicide from the WSSA Group 15 is acetochlor or flufenacet.
- a or the additional herbicide with which the herbicidal combinations or compositions according to the present disclosure may be combined or mixed is glyphosate and/or salts thereof.
- preferred salts of glyphosate are the mono-salts and di-salts of glyphosate and monoethanolamine, diethanolamine, triethanolamine, dimethylamine, n- propylamine, isopropylamine, trimesium, potassium or sodium, and combinations thereof.
- the herbicidal combinations of the disclosure can be applied in a manner known to the skilled person, as for example together (for example as a co -formulation or as a tank mix) or else a short time after one another (splitting), for example to the plants, plant parts or plant seeds or to the area on which the plants are growing.
- Preference here is given to joint or near-synchronous application of components (A) and (B).
- Also preferred is application from pre-emergence up to early post-emergence.
- the present disclosure relates to a method for controlling weed plants in crops of useful plants, characterized in that a herbicidal combination or composition according to the present disclosure is applied to the weed plants, plants, plant seeds, or to the area on which the weed plants are growing.
- the present disclosure relates the use of a herbicidal combination or composition according to the present disclosure for controlling unwanted plants in crops of useful plants.
- weed plants When the herbicidal combinations or compositions of the disclosure are used, a very broad spectrum of weed plants are controlled pre-emergence and postemergence, examples being annual and perennial monocotyledonous or dicotyledonous weeds, and also unwanted crop plants.
- herbicidal combinations or compositions of the disclosure are particularly suitable for use in crops such as cereals, maize (com), rice, soybean, oilseed rape, sugarbeet, cotton and sugarcane, and for use in long-term crops, in plantations and on noncrop land. Preference is given to their use in crops of com, cotton and soybean. They are also very suitable for use in transgenic crops of com, cotton and soybean.
- a preferred method or use according to the present disclosure is characterized in that the crop plants are selected from the group consisting of corn, cotton and soybean.
- the method or use according to the present disclosure preferably is characterized in that the crop plants have been genetically modified.
- the present disclosure accordingly further provides a method for controlling unwanted plants in plant crops that is characterized in that components (A) and (B) of the herbicidal combinations or compositions of the disclosure are applied to the plants (e.g. weed plants such as monocotyledonous or dicotyledonous weeds or unwanted crop plants) or to the area on which the plants are growing, such application taking place jointly or separately, for example.
- the plants e.g. weed plants such as monocotyledonous or dicotyledonous weeds or unwanted crop plants
- the area on which the plants are growing such application taking place jointly or separately, for example.
- Monocotyledonous weeds belong, for example, to the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecums and Apera.
- Dicotyledonous weeds belong, for example, to the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Kochia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindemia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum and Euphorbia.
- the present disclosure also provides for the use of the herbicidal combinations or compositions of the disclosure for controlling unwanted plant growth, preferably in crops of useful plants.
- said method or use is carried out for controlling weeds or plants having a resistance to herbicides of one, two, three, four, five or more different Modes of Action, wherein the resistances preferably are selected from the group consisting of auxin herbicide resistance, glyphosate resistance, acetolactate synthase (ALS) inhibitor resistance, 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor resistance, CoA carboxylase (ACCase) inhibitor resistance, photosystem I (PS I) inhibitor resistance, photosystem II (PS II) inhibitor resistance, protoporphyrinogen oxidase (PPG) inhibitor resistance and synthesis of very long-chain fatty acid (VLCFA) inhibitor resistance.
- the resistances preferably are selected from the group consisting of auxin herbicide resistance, glyphosate resistance, acetolactate synthase (ALS) inhibitor resistance, 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor resistance, CoA carboxylase (ACCase) inhibitor resistance
- weeds that are resistant to or are evolving resistance to one or to multiple Modes of Action, in particular resistance to one or more herbicides selected from the group consisting of glyphosate, auxin herbicides (auxins), ALS inhibitor herbicides, PSII inhibitor herbicides, HPPD inhibitor herbicides, PPO inhibitor herbicides and/or VLCFA inhibitor herbicides.
- auxins auxin herbicides
- ALS inhibitor herbicides PSII inhibitor herbicides
- HPPD inhibitor herbicides HPPD inhibitor herbicides
- PPO inhibitor herbicides and/or VLCFA inhibitor herbicides.
- said method or use is carried out for controlling weeds or plants having a resistance to HPPD-inhibitor herbicides.
- said method or use is carried out for controlling weeds or plants having a resistance to HPPD-inhibitor herbicides and one, two, three of four further resistances mentioned above, preferably selected from the group consisting of glyphosate resistance, acetolactate synthase (ALS) inhibitor resistance, photosystem II (PS II) inhibitor resistance, protoporphyrinogen oxidase (PPO) inhibitor resistance.
- glyphosate resistance acetolactate synthase (ALS) inhibitor resistance
- PS II photosystem II
- PPO protoporphyrinogen oxidase
- resistant weeds in the context of the present disclosure include the following dicotyledonous resistant weeds: Amaranthus palmeri, Amaranthus tuberculatus, Kochia scoparia, Chenopodium album, Ambrosia trifida, and Ambrosia artemisiifolia. Particularly relevant examples of such resistant weeds are Amaranthus palmeri and Amaranthus tuberculatus.
- the application rate of rimisoxafen typically is at least about 35 g/ha (active ingredient in gram per hectare)
- the application rate of diflufenican typically is at least about 35 g/ha (active ingredient in gram per hectare)
- the application rate of mesotrione typically is at least about 50 g/ha (active ingredient in gram per hectare).
- the application rate of rimisoxafen typically is from about 35 to about 200 g/ha (active ingredient in gram per hectare), preferably from about 75 g/ha to about 175 g/ha. In a preferred embodiment, the application rate of rimisoxafen is in the range of about 100 g/ha to about 200 g/ha, such as 100 g/ha, 105 g/ha, 125 g/ha, or 150 g/ha.
- the application rate of diflufenican typically is from about 35 to about 200 g/ha (active ingredient in gram per hectare), preferably from about 75 g/ha to about 175 g/ha. In a preferred embodiment, the application rate of diflufenican is about 150 g/ha.
- a preferred method or use according to the present disclosure is characterized in that the components (A) and (B) and optionally (C) of the combinations of the present disclosure are applied sequentially, wherein the order of application may be flexibly defined according to needs.
- Another preferred method or use according to the present disclosure is characterized in that the components (A) and (B) and optionally (C) are applied together.
- Another preferred method or use according to the present disclosure is characterized in that the components (A) and (B) and optionally (C) are applied together as a single composition.
- the herbicidal combinations of the disclosure can be produced by known methods, for example as mixed formulations of the individual components, optionally with further active ingredients, adjuvants and/or customary formulation assistants, these combinations being then employed in a customary way as dilutions with water, or may be produced in the form of what are called tank mixes, by joint dilution of the separately formulated or partially separately formulated individual components with water.
- the temporally offset application split application of the separately formulated or partially separately formulated individual components.
- Another possibility is the application of the individual components or of the herbicidal combinations in two or more portions (sequential application), as for example after applications pre-emergence, followed by postemergence applications, or after early postemergence applications, followed by applications in the middle or late post-emergence phase. Preference here is given to the joint or near- synchronous application of the active ingredients of the respective combination.
- transgenic plants are notable for special advantageous properties, for example for resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or organisms that cause plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses.
- Other special properties relate, for example, to the harvested material with regard to quantity, quality, storability, combination and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or with a different fatty acid combination in the harvested material.
- Other special properties may be tolerance or resistance to abiotic stressors, for example heat, low temperatures, drought, salinity and ultraviolet radiation.
- nucleic acid molecules which allow mutagenesis or a sequence change by recombination of DNA sequences can be introduced into plasmids.
- base exchanges remove parts of sequences or add natural or synthetic sequences.
- adaptors or linkers can be attached to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene und Klone” [Genes and Clones], VCH Weinheim 2nd edition 1996.
- the production of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.
- DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present and also DNA molecules which only encompass portions of the coding sequence, it being necessary for these portions to be long enough to have an antisense effect in the cells.
- DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them is also possible.
- the protein synthesized may be localized in any desired compartment of the plant cell.
- sequences are known to the skilled person (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
- the nucleic acid molecules can also be expressed in the organelles of the plant cells.
- the transgenic plant cells can be regenerated by known techniques to give whole plants.
- the transgenic plants may be plants of any desired plant species, i.e. both monocotyledonous and dicotyledonous plants.
- the combinations or compositions according to the disclosure can be used in transgenic crop plants (crops) which are resistant to auxin herbicides such as, for example, dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or 4- hydroxyphenylpyruvate dioxygenases (HPPD).
- auxin herbicides such as, for example, dicamba
- ALS acetolactate synthases
- EPSP synthases EPSP synthases
- glutamine synthases GS
- HPPD 4- hydroxyphenylpyruvate dioxygenases
- the effects toward weed plants observed in other crops are often also accompanied by effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.
- the disclosure therefore also provides for the use of the combinations or compositions of the disclosure for controlling weed plants in transgenic crop plants.
- the disclosure therefore also provides for the use of the combinations or compositions of the disclosure for controlling weed plants in transgenic crop plants or crop plants having tolerance through selective breeding.
- the components (A) and (B) and (C) can be converted together or separately into customary formulations, for example for application by spraying, watering and sprinkling, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient-impregnated natural and synthetic substances, and microencapsulations in polymeric substances.
- the formulations may comprise the customary auxiliaries and adjuvants.
- formulations are produced in a known manner, for example by mixing the components (A) and (B) and (C) with extenders, i.e. liquid solvents, pressurized liquefied gases and/or solid carriers, optionally with use of surfactants, i.e. emulsifiers and/or dispersants and/or foam formers.
- extenders i.e. liquid solvents, pressurized liquefied gases and/or solid carriers
- surfactants i.e. emulsifiers and/or dispersants and/or foam formers.
- Useful solid carriers include: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; useful solid carriers for granules include: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours, and granules of organic material, such as sawdust, coconut shells, maize cobs and tobacco stalks; useful emulsifiers and/or foam formers include: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
- alkylaryl polyglycol ethers alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates
- useful dispersants include: for example lignosulphite waste liquors and methylcellulose.
- A efficacy of the active ingredient (A) in % at an application rate of a [g a.i./ha] ;
- B efficacy of the active ingredient (B) in % at an application rate of b [g a.i./ha] ;
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Abstract
La présente invention concerne principalement certaines combinaisons herbicides agrochimiquement actives comprenant (A) du rimisoxafène, et (B) du diflufénican, ou (A) du rimisoxafène, (B) du diflufénican et (C) de la mésotrione. L'invention concerne en outre l'utilisation de ces combinaisons pour lutter contre les mauvaises herbes, en particulier pour lutter contre les mauvaises herbes résistantes, et des procédés correspondants.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202463574453P | 2024-04-04 | 2024-04-04 | |
| US63/574,453 | 2024-04-04 |
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| Publication Number | Publication Date |
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| WO2025209889A1 true WO2025209889A1 (fr) | 2025-10-09 |
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| PCT/EP2025/058160 Pending WO2025209889A1 (fr) | 2024-04-04 | 2025-03-25 | Compositions herbicides |
| PCT/EP2025/058168 Pending WO2025209890A1 (fr) | 2024-04-04 | 2025-03-25 | Compositions herbicides |
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| PCT/EP2025/058168 Pending WO2025209890A1 (fr) | 2024-04-04 | 2025-03-25 | Compositions herbicides |
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| WO2015108779A1 (fr) | 2014-01-16 | 2015-07-23 | E. I. Du Pont De Nemours And Company | Dérivés de pyrimidinyloxy benzène à utiliser en tant qu'herbicides |
| WO2022202642A1 (fr) * | 2021-03-22 | 2022-09-29 | 日本曹達株式会社 | Composition herbicide |
| JP2024166574A (ja) * | 2023-05-19 | 2024-11-29 | 株式会社エス・ディー・エス バイオテック | 除草剤組成物および有害雑草を防除する方法 |
| WO2025049862A1 (fr) * | 2023-09-01 | 2025-03-06 | Syngenta Crop Protection Ag | Compositions herbicides |
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2025
- 2025-03-25 WO PCT/EP2025/058160 patent/WO2025209889A1/fr active Pending
- 2025-03-25 WO PCT/EP2025/058168 patent/WO2025209890A1/fr active Pending
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