[go: up one dir, main page]

WO2025073561A1 - Combinaison herbicide/phytoprotecteur sur la base d'un traitement de graines avec des phytoprotecteurs appartenant à la classe de l'acide [(1,5-diphényl-1h-1,2,4-triazol-3-yl) oxy]acétique substitué et ses sels - Google Patents

Combinaison herbicide/phytoprotecteur sur la base d'un traitement de graines avec des phytoprotecteurs appartenant à la classe de l'acide [(1,5-diphényl-1h-1,2,4-triazol-3-yl) oxy]acétique substitué et ses sels Download PDF

Info

Publication number
WO2025073561A1
WO2025073561A1 PCT/EP2024/077001 EP2024077001W WO2025073561A1 WO 2025073561 A1 WO2025073561 A1 WO 2025073561A1 EP 2024077001 W EP2024077001 W EP 2024077001W WO 2025073561 A1 WO2025073561 A1 WO 2025073561A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
formula
oxy
difluorophenyl
fluorophenyl
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
Application number
PCT/EP2024/077001
Other languages
English (en)
Inventor
Julio PEREZ CATALAN
Jan Dittgen
Hubert Menne
Mathias Schmidt
Thomas Müller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of WO2025073561A1 publication Critical patent/WO2025073561A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • 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
    • 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
    • A01P13/02—Herbicides; Algicides selective

Definitions

  • the invention relates to novel methods for preventing crop damage, which comprise seed treatment of a crop seed with a safener compound based on a substituted [(l,5-diphenyl-lH-l,2,4-triazol-3-yl)oxy]acetic acid or agrochemically acceptable salt thereof, followed by application of a herbicidal compound based on a substituted isoxazolincarboxamide or agrochemically acceptable salt thereof.
  • a safener compound based on a substituted [(l,5-diphenyl-lH-l,2,4-triazol-3-yl)oxy]acetic acid or agrochemically acceptable salt thereof
  • a herbicidal compound based on a substituted isoxazolincarboxamide or agrochemically acceptable salt thereof.
  • Substituted isoxazolincarboxamides are already known as effective herbicides from WO2018/228985 and WO2019/145245.
  • the activity of these compounds and/or their compatibility with crop plants are not entirely satisfactory under all conditions, such that the use of different safeners has been considered, e.g. described in W02021/245003, W02021/245004, W02021/245005, W02021/245006, W02021/245007, W02021/245008, W02021/245009.
  • Substituted [(l,5-diphenyl-lH-l,2,4-triazol-3-yl)oxy]acetic acids and salts thereof are a novel class of safeners first described in W02021/105101.
  • Combinations of substituted [(l,5-diphenyl-lH-l,2,4-triazol-3- yl)oxy]acetic acids with different classes of herbicides are furthermore described in WO2022/238194.
  • the present invention thus provides a method for reducing crop damage, comprising treating seeds of the crop with a safener compound of formula (II) before sowing,
  • (R 1 ) n ’ -phenyl is presented by one of the groups Q-l.l to Q-1.55 and (R 2 ) m -phenyl is selected from one of the groups Q-2.1 to Q-2.55
  • R 3 is hydrogen
  • R 4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-yl-methyl, tetrahydropyran-2-yl-methyl, tetrahydropyran-3-yl-methyl, tetrahydropyran-4-yl-methyl, methylpropionat-3-yl, ethylpropionat-3-yl, methylacetat-2-yl, ethylacetat-2-yl, methylpivalat-2-yl, ethylpivalat-3-yl, methyl-2-methylpropanoat-3-yl, methyl-2
  • the compound of formula (I) is a compound of formula (la) or an agrochemically acceptable salt thereof, in which
  • X 3 , X 5 , R 3 and G are as described above;
  • Z means Z-la, Z-lb, Z-2a, Z-3a, Z-4a, Z-5a, Z-6a, Z-7a, or Z-8a,
  • Z-8a wherein Z-4a means the mixture of both structures Z-4b and Z-4c and wherein Z-8a means the mixture of both structures Z-8b and Z-8c and wherein the arrow means a bond to the group CO-G in formula (la).
  • the compound of formula (la) is selected from the compounds of below table 1 or agrochemically acceptable salts thereof.
  • the compounds of formula (I) are known from WO2018/228985 and WO2019/145245 and can be synthesized according to the processes described therein. Even further preferably, the compound of formula (I) is selected from
  • the compound of formula (II) is selected from
  • Such compounds of formula (II) are for example described in W02021/105101 and can be synthesized according to the processes described therein.
  • preferred safener compounds of formula (II) in the context of the present invention are compounds Al, A3, A5, A7 and A9 of the previous table 2.
  • the herbicidal compound of formula (I) is Methyl (2R* ,4R*)-4- [ [(5 S) -3 -(3 ,5 -difluorophenyl)-5 - vinyl-4H-isoxazol-5 -carbonyl] amino] tetrahydrofuran- 2-carboxylate; and the safener compound of formula (II) is selected from
  • the herbicidal compound of formula (I) is
  • the herbicidal compound of formula (I) is applied in a pre-emergent treatment.
  • the herbicidal compound of formula (I) is applied in a post-emergent treatment, preferably in an early or mid post-emergent treatment.
  • the crop is a genetically modified plant.
  • the safener compound (II) is applied to the seeds in an application rate of between 0.01 and 2 g per kg seed, preferably between 0.1 and 1 g per kg seed, further preferably between 0.2 and 0.8 g per kg seed, even further preferably between 0.2 and 0.5 g per kg seed.
  • the herbicidal compound of formula (I) is applied at an application rate of between 0.1 and 1000 g per ha, preferably between 0.5 and 500 g per ha, further preferably between 0.7 and 100 g per ha, even further preferably between 1 and 50 g per ha.
  • the method further comprises applying the safener compound of formula (II) after sowing in a in a pre-emergent or post-emergent treatment.
  • the safener compound of formula (II) is applied in a tank-mix together with the herbicidal compound of formula (I).
  • the safener compound of formula (II) is applied in a tank-mix together with the herbicidal compound of formula (I) at an application rate of between 1 and 1000 g per ha, preferably between 5 and 500 g per ha, further preferably between 10 and 100 g per ha, even further preferably between 25 and 75 g per ha.
  • Halogen represents radicals of fluorine, chlorine, bromine and iodine. Preference is given to the radicals of fluorine and chlorine.
  • Alkyl means saturated straight-chain or branched hydrocarbyl radicals having the number of carbon atoms specified in each case, e.g. Ci-Ce-alkyl such as methyl, ethyl, propyl, 1 -methylethyl, butyl, 1- methylpropyl, 2-methylpropyl, 1,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl,
  • Alkenyl means unsaturated straight-chain or branched hydrocarbyl radicals having the number of carbon atoms specified in each case and one double bond in any position, e.g. Cz-Ce-alkenyl such as ethenyl, 1- propenyl, 2-propenyl, 1 -methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl- 1 -propenyl, 2-methyl- 1 -propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl- 1-butenyl, 2-methyl- 1-butenyl, 3-methyl- 1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-
  • Alkynyl represents a straight-chain or branched hydrocarbyl groups having 2 to 8, preferably 2 to 6, carbon atoms and one triple bond in any position.
  • Non-limiting examples include ethynyl, prop-l-ynyl, prop-2-ynyl, but-l-ynyl, but-2-ynyl, but-3-ynyl, l-methylprop-2-ynyl, pent-l-ynyl, pent-2-ynyl, pent-3- ynyl, pent-4-ynyl, l-methylbut-2-ynyl, l-methylbut-3-ynyl, 2-methylbut-3-ynyl, 3-methylbut-l-ynyl, l,l-dimethylprop-2-ynyl, l-ethylprop-2-ynyl, hex-l-ynyl, hex-2-ynyl, hex-3-ynyl
  • Cycloalkyl means a carbocyclic saturated ring system having preferably 3-8 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • cyclic systems with substituents are included, also including substituents with a double bond on the cycloalkyl radical, for example an alkylidene group such as methylidene.
  • Alkoxy means saturated straight-chain or branched alkoxy radicals having the number of carbon atoms specified in each case, for example Ci-Ce-alkoxy such as methoxy, ethoxy, propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy, 1,1 -dimethylethoxy, pentoxy, 1 -methylbutoxy, 2- methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1,1 -dimethylpropoxy,
  • Ci-Ce-alkoxy such as methoxy, ethoxy, propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy, 1,1 -dimethylethoxy, pentoxy, 1 -methylbutoxy, 2- methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1,1 -dimethylprop
  • Halogen-substituted alkoxy means straight-chain or branched alkoxy radicals having the number of carbon atoms specified in each case, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above, e.g.
  • Ci- Cz-haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 -bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-l,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and l,l,l-trifluoroprop-2-oxy.
  • the safenening effect of the compounds of formula (II) is higher compared to the safening effect of other known known safeners or antidotes which are generally capable of antagonizing the damaging effect of a herbicide on the crop plants, when followed by herbicidal treatment with substituted isoxazolincarboxamides of the general formula (I).
  • Emphasis is given here to the particularly advantageous effect of a crop seed treatment with compounds of formula (II) with respect to sparing cereal plants, such as, for example, wheat, barley and rye, but also maize and rice, as crop plants.
  • the active compound combinations according to the invention can be used, for example, in connection with the following plants:
  • Dicotyledonous crops of the genera Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cuburbita, Helianthus.
  • Monocotyledonous crops of the genera Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.
  • crop plants are all plants and plant varieties including transgenic plants and plant varieties, where on transgenic plants and plant varieties it is also possible for synergistic effects to occur.
  • compositions within the context of the present invention comprise in addition to the herbicide compound of formula (I) according to the invention one or more further component(s) which include, but are not limited to the following: formulation auxiliaries, additives customary in crop protection, further agrochemically active compounds (e.g. fungicides and insecticides). Such compositions may also be applied in the method according to the invention.
  • the method according to the present invention comprises applying at least one further herbicide (c) wherein (c) is chosen from the list which includes but is not limited to the following: Acetochlor, acifluorfen, acifluorfen-methyl, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid- dimethylammonium, aminopyralid- tripromine, amitrole, ammoniumsulfamate, anilofos, asulam, asulam-potassium, asulam sodium
  • dicamba-biproamine dicamba-N,N-Bis(3-aminopropyl)methylamine, dicamba-butotyl, dicamba-choline, dicamba-digly colamine, dicamba-dimethylammonium, dicamba- diethanolaminemmonium, dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl, dicamba-monoethanolaminedicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba- triethanolamine, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl- 1 ,2-oxazolidin-3-one, 2-(2,5- dichlorobenzyl)-4,4-dimethyl- 1 ,2-oxazolidin-3-one, dichlorprop, dichlorprop-butotyl, dichlroprop- dimethylammonium, dichhlorprop-
  • COs sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc residues but have side chain decorations that make them different from chitin molecules [(CsHoNOsln, CAS No. 1398-61-4] and chitosan molecules [(CsHnNOrln, CAS No.
  • chitinous compounds chlormequat chloride, cloprop, cyclanilide, 3-(Cycloprop-l-enyl)propionic acid, daminozide, dazomet, dazomet-sodium, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurenol- methyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4-indol-3- ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, Jasmonic acid or derivatives thereof (e.g.
  • LCO lipo-chitooligosaccharides
  • Nod symbiotic nodulation
  • Myc factors consist of an oligosaccharide backbone of P-l,4-linked N-acetyl-D-glucosamine (“GlcNAc”) residues with an N-linked fatty acyl chain condensed at the non-reducing end.
  • LCOs differ in the number of GlcNAc residues in the backbone, in the length and degree of saturation of the fatty acyl chain and in the substitutions of reducing and non-reducing sugar residues), linoleic acid or derivatives thereof, linolenic acid or derivatives thereof, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1 -methylcyclopropene, 3 ’-methyl abscisic acid, 2-(l-naphthyl)acetamide, 1 -naphthylacetic acid, 2- naphthyloxyacetic acid, nitrophenolate-mixture, 4-Oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmon, salicylic
  • Pre-emergent application refers to a herbicide which is applied to an area of interest (e.g., a field or area of cultivation) before a plant emerges visibly from the soil.
  • Post-emergent application refers to a herbicide which is applied to an area after a plant emerges visibly from the soil.
  • pre- emergent and post-emergent may be defined via the BBCH code.
  • the BBCH code commonly known to the person skilled in the art, provides information on the stage of morphological development of a plant.
  • the abbreviation officially represents the Federal Department of Biology, Federal Register of Plant Varieties and Chemical Industry.
  • PE prior to seed germination or up to BBCH stage 09
  • Post-emergent (PO) application on the aboveground parts of the plant; BBCH stages 10-31.
  • Late post-emergent BBCH stages 29-31.
  • the BBCH code may apply to both the emergence of a weed or of a planted crop.
  • the BBCH code refers to the emergence of the crop. Examples:
  • TRZAW winter wheat
  • the safener compound A3 (see table 2 above) according to the invention, as well as the comparative safeners mefenpyr-diethyl (CAS 135590-91-9) and cloquintocet-mexyl (CAS 99607- 70-2) were used.
  • each safener was tank-mixed with water.
  • the water is used to ensure right kernel distribution of the compound on it.
  • the slurry volume (water+safener) is 800 ml/100 kg seeds.
  • the seeds to be treated were put in a mixing chamber of the equipment for seed treatment. Once seeds are placed in the equipment, the slurry volume was introduced in the mixing chamber for a duration of 20 seconds (to complete the seed treatment). Treated seeds were collected then from the mixing chamber and dried in a paper bag.
  • the dose rate of the seed treatment was 50 g safener / 100 kg seeds.
  • Seeds of the eight varieties of TRZAW treated with safeners as described under 1. above as well as untreated seeds were planted in strips in the field with 4 rows of TRZAW per each of the treatments in 4 trials around Europe (DE, FR, PL, IT).
  • % crop damage from the herbicide application observed on the different strips was scored visually in comparison to control strips (that had not received a herbicide application but containing seed treatment and not seed treatment).
  • [Average crop damage] % (herbicide damage on strips (with and without safener seed treatment) treated with the herbicide - herbicide damage on strips (with and without safener seed treatment) non treated with the herbicide) *100
  • the herbicidal activity (%) on Alopecurus myosuroides (ALOMY) and Avena sativa (AVESA) was determined by the overall difference (%) of the biomass and other symptoms (i.e. chlorosis, necrosis, stunting) between the treated plots with the herbicide and the untreated plots.
  • the safener compound A3 provides for a higher safening function of the crop compared to the safeners mefenpyr-diethyl or cloquintocet-mexyl, as shown in the tables above. At the same time, the herbicidal activity of HER is not affected by the safener compound A3. B. Efficacy of different modes of safener application
  • test plants were treated post-emergent in growth stage BBCH11.
  • HER Metal (2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazol-5- carbonyl] amino] tetrahydrofuran-2-carboxylate: EC 10g/l
  • the application rate of HER was 2 g /ha; the application rate of compound A3 was 50 g/ha.
  • the plants were further cultivated as described above. 28 days after application, the herbicide damage was scored visually. The damage was evaluated visually on a scale of 0-100% in comparison to control plants without herbicide and safener treatment.
  • the crop damage could be unexpectedly reduced by applying the safener as seed treatment when compared to tank- mixing the safener with the herbicides.
  • An even further unexpected reduction of crop damage was achieved by applying the safener twice, namely both in terms of seed treatment and as tank-mix partner to the herbicide.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouveaux procédés de réduction de dommages causés aux cultures comprenant des applications pour le traitement de graines de phytoprotecteurs suivies d'un traitement pré- ou post-émergence avec des isoxazolincarboxamides substitués agissant de manière herbicide.
PCT/EP2024/077001 2023-10-02 2024-09-26 Combinaison herbicide/phytoprotecteur sur la base d'un traitement de graines avec des phytoprotecteurs appartenant à la classe de l'acide [(1,5-diphényl-1h-1,2,4-triazol-3-yl) oxy]acétique substitué et ses sels Pending WO2025073561A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP23201166 2023-10-02
EP23201166.8 2023-10-02

Publications (1)

Publication Number Publication Date
WO2025073561A1 true WO2025073561A1 (fr) 2025-04-10

Family

ID=88237411

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2024/077001 Pending WO2025073561A1 (fr) 2023-10-02 2024-09-26 Combinaison herbicide/phytoprotecteur sur la base d'un traitement de graines avec des phytoprotecteurs appartenant à la classe de l'acide [(1,5-diphényl-1h-1,2,4-triazol-3-yl) oxy]acétique substitué et ses sels

Country Status (2)

Country Link
AR (1) AR134007A1 (fr)
WO (1) WO2025073561A1 (fr)

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018228985A1 (fr) 2017-06-13 2018-12-20 Bayer Aktiengesellschaft 3-phénylisoxazoline-5-carboxamides d'acides carboxyliques et d'esters de tétrahydro- et dihydrofurane à effet herbicide
WO2019145245A1 (fr) 2018-01-25 2019-08-01 Bayer Aktiengesellschaft 3-phényl-isoxazoline-5-carboxamides de dérivés d'acide cyclopentényl-carboxylique à action herbicide
WO2021105101A1 (fr) 2019-11-26 2021-06-03 Bayer Aktiengesellschaft Dérivés d'acide acétique [(1,5-diphényl-1h-1,2,4-triazol-3-yl)oxy] et sels de ceux-ci, compositions de protection des cultures les comprenant, leurs procédés de production et utilisation de ceux-ci en tant que phytoprotecteurs
WO2021245006A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et de furilazole
WO2021245003A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et d'isoxadifène-éthyle
WO2021245007A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et de méfénpyr-diéthyle
WO2021245004A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline-carboxamides substitués et de cloquintocet-mexyl
WO2021245005A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et de cyprosulfamide
WO2021245009A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et de metcamifène
WO2021245008A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et de benoxacor
WO2022238194A1 (fr) 2021-05-10 2022-11-17 Bayer Aktiengesellschaft Combinaison herbicide(s)/phytoprotecteur(s) à base de phytoprotecteurs de la classe des acides [(1,5-diphényl-1h-1,2,4-triazol-3-yl)oxy] acétiques substitués et leurs sels
WO2023001679A1 (fr) * 2021-07-19 2023-01-26 Bayer Aktiengesellschaft Procédé d'application de traitement par points contre les mauvaises herbes

Patent Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018228985A1 (fr) 2017-06-13 2018-12-20 Bayer Aktiengesellschaft 3-phénylisoxazoline-5-carboxamides d'acides carboxyliques et d'esters de tétrahydro- et dihydrofurane à effet herbicide
US11597724B2 (en) * 2017-06-13 2023-03-07 Bayer Aktiengesellschaft Herbicidally active 3-phenylisoxazoline-5-carboxamides of tetrahydro and dihydrofuran carboxylic acids and esters
WO2019145245A1 (fr) 2018-01-25 2019-08-01 Bayer Aktiengesellschaft 3-phényl-isoxazoline-5-carboxamides de dérivés d'acide cyclopentényl-carboxylique à action herbicide
US20220306591A1 (en) * 2018-01-25 2022-09-29 Bayer Aktiengesellschaft Herbicidally active 3-phenylisoxazoline-5-carboxamides of cyclopentenylcarboxylic acid derivatives
WO2021105101A1 (fr) 2019-11-26 2021-06-03 Bayer Aktiengesellschaft Dérivés d'acide acétique [(1,5-diphényl-1h-1,2,4-triazol-3-yl)oxy] et sels de ceux-ci, compositions de protection des cultures les comprenant, leurs procédés de production et utilisation de ceux-ci en tant que phytoprotecteurs
WO2021245007A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et de méfénpyr-diéthyle
US20230200390A1 (en) * 2020-06-02 2023-06-29 Bayer Aktiengesellschaft Selective herbicides based on substituted isoxazolin carboxamides and mefenpyr-diethyl
WO2021245005A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et de cyprosulfamide
WO2021245009A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et de metcamifène
WO2021245008A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et de benoxacor
WO2021245003A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et d'isoxadifène-éthyle
US20230276792A1 (en) * 2020-06-02 2023-09-07 Bayer Aktiengesellschaft Selective herbicides based on substituted isoxazolin carboxamides and cloquintocet-mexyl
US20230240297A1 (en) * 2020-06-02 2023-08-03 Bayer Aktiengesellschaft Selective herbicides based on substituted isoxazolin carboxamides and cyprosulfamide
WO2021245006A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline carboxamides substitués et de furilazole
US20230189808A1 (en) * 2020-06-02 2023-06-22 Bayer Aktiengesellschaft Selective herbicides based on substituted isoxazolin carboxamides and furilazole
WO2021245004A1 (fr) 2020-06-02 2021-12-09 Bayer Aktiengesellschaft Herbicides sélectifs à base d'isoxazoline-carboxamides substitués et de cloquintocet-mexyl
US20230200393A1 (en) * 2020-06-02 2023-06-29 Bayer Aktiengesellschaft Selective herbicides based on substituted isoxazolin carboxamides and metcamifen
US20230200394A1 (en) * 2020-06-02 2023-06-29 Bayer Aktiengesellschaft Selective herbicides based on substituted isoxazolin carboxamides and benoxacor
US20230217926A1 (en) * 2020-06-02 2023-07-13 Bayer Aktiengesellschaft Selective herbicides based on substituted isoxazolin carboxamides and isoxadifen-ethyl
WO2022238194A1 (fr) 2021-05-10 2022-11-17 Bayer Aktiengesellschaft Combinaison herbicide(s)/phytoprotecteur(s) à base de phytoprotecteurs de la classe des acides [(1,5-diphényl-1h-1,2,4-triazol-3-yl)oxy] acétiques substitués et leurs sels
WO2023001679A1 (fr) * 2021-07-19 2023-01-26 Bayer Aktiengesellschaft Procédé d'application de traitement par points contre les mauvaises herbes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
no. 9012-76-4

Also Published As

Publication number Publication date
AR134007A1 (es) 2025-11-26

Similar Documents

Publication Publication Date Title
US20230276792A1 (en) Selective herbicides based on substituted isoxazolin carboxamides and cloquintocet-mexyl
AU2021285006A1 (en) Selective herbicides based on substituted isoxazolin carboxamides and mefenpyr-diethyl
AU2021286151A1 (en) Selective herbicides based on substituted isoxazolin carboxamides and isoxadifen-ethyl
WO2021245009A1 (fr) Herbicides sélectifs à base d'isoxazoline carboxamides substitués et de metcamifène
US20230189808A1 (en) Selective herbicides based on substituted isoxazolin carboxamides and furilazole
AU2021285005A1 (en) Selective herbicides based on substituted isoxazolin carboxamides and cyprosulfamide
US20230200394A1 (en) Selective herbicides based on substituted isoxazolin carboxamides and benoxacor
WO2025073561A1 (fr) Combinaison herbicide/phytoprotecteur sur la base d'un traitement de graines avec des phytoprotecteurs appartenant à la classe de l'acide [(1,5-diphényl-1h-1,2,4-triazol-3-yl) oxy]acétique substitué et ses sels
EA048095B1 (ru) Селективные гербициды на основе замещенных изоксазолин карбоксамидов и ципросульфамида

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24776305

Country of ref document: EP

Kind code of ref document: A1