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WO2025114265A1 - Arylcarboxamides substitués - Google Patents

Arylcarboxamides substitués Download PDF

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Publication number
WO2025114265A1
WO2025114265A1 PCT/EP2024/083582 EP2024083582W WO2025114265A1 WO 2025114265 A1 WO2025114265 A1 WO 2025114265A1 EP 2024083582 W EP2024083582 W EP 2024083582W WO 2025114265 A1 WO2025114265 A1 WO 2025114265A1
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WO
WIPO (PCT)
Prior art keywords
methyl
alkyl
chloro
acid
compounds
Prior art date
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PCT/EP2024/083582
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German (de)
English (en)
Inventor
Christian Waldraff
Hartmut Ahrens
Harald Jakobi
Birgit BOLLENBACH-WAHL
Elisabeth ASMUS
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Bayer AG
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Bayer AG
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Publication of WO2025114265A1 publication Critical patent/WO2025114265A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings

Definitions

  • the invention relates to the technical field of herbicides, in particular to herbicides for the selective control of weeds and grass weeds in crops.
  • WO 2020/148175 and the documents cited therein describe herbicidally active benzoylamides. These benzoylamides can be substituted in the 3-position of the phenyl ring by a variety of different residues. However, the benzoylamides known from these documents do not always exhibit sufficient herbicidal activity and/or tolerance to crop plants.
  • the object of the present invention is to provide alternative herbicidally active ingredients. This object is achieved by the arylcarboxamides according to the invention described below, which bear a sulfur-containing radical linked via a methylene group in the 3-position of the phenyl ring and a haloalkoxy radical in the 4-position.
  • the present invention therefore relates to arylcarboxamides of the formula (I) and their salts where the symbols and indices have the following meanings:
  • R x means (Ci-C 6 )-alkyl
  • X is halogen or (Ci-Ce)-alkyl
  • Y means halogen-(Ci-C6)-alkoxy
  • Z means (Ci-Ce)-alkyl, (Cs-Cej-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C6)-alkyl or (Ci-Ce)-alkyl-
  • n 0, 1 or 2.
  • alkyl radicals with more than two carbon atoms can be straight-chain or branched.
  • Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl.
  • alkenyl is, for example, allyl, l-methylprop-2-en-l-yl, 2-methyl-prop-2-en-l-yl, but-2-en-l-yl, but-3-en-l-yl, l-methyl-but-3-en-l-yl and l-methyl-but-2-en-l-yl.
  • Alkynyl is, for example, propargyl, but-2-yn-l-yl, but-3-yn-l-yl, l-methyl-but-3-yn-l-yl.
  • the multiple bond can be located in any position of the unsaturated residue.
  • Cycloalkyl means a carbocyclic, saturated ring system.
  • Halogen-substituted alkyl means straight-chain or branched alkyl groups, where in these groups the hydrogen atoms may be partially or completely replaced by halogen atoms, e.g.
  • C1-C2-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl.
  • Halogen stands for fluorine, chlorine, bromine or iodine.
  • the compounds of the general formula (I) or (II) can exist as stereoisomers depending on the nature and linkage of the substituents. For example, if one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers also occur when n is 1 (sulfoxides). Stereoisomers can be obtained from the mixtures obtained during production by conventional separation methods, for example by chromatographic separation processes. Stereoisomers can also be selectively prepared by using stereoselective reactions using optically active starting materials and/or auxiliaries.
  • the invention also relates to all stereoisomers and mixtures thereof which are encompassed by the general formula (I) or (II) but are not specifically defined.
  • the compounds of the formula (I) can form salts.
  • Suitable bases include, for example, organic amines such as trialkylamines, morpholine, piperidine, or pyridine, as well as ammonium, alkali, or alkaline earth metal hydroxides, carbonates, and bicarbonates, particularly sodium and potassium hydroxide, sodium and potassium carbonate, and sodium and potassium bicarbonate.
  • salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, particularly alkali metal salts or alkaline earth metal salts, particularly sodium and potassium salts, or ammonium salts, salts with organic amines, or quaternary ammonium salts, for example with cations of the formula [NRR ⁇ R ⁇ ⁇ R ⁇ ⁇ ] + , in which R to R ⁇ ⁇ ⁇ each independently represent an organic radical, particularly alkyl, aryl, aralkyl, or alkylaryl.
  • metal salts particularly alkali metal salts or alkaline earth metal salts, particularly sodium and potassium salts, or ammonium salts, salts with organic amines, or quaternary ammonium salts, for example with cations of the formula [NRR ⁇ R ⁇ ⁇ R ⁇ ⁇ ] + , in which R to R ⁇ ⁇ ⁇ each independently represent an organic radical, particularly alkyl, aryl,
  • Alkylsulfonium and alkylsulfoxonium salts are also suitable.
  • the compounds of formula (I) can form salts by addition of a suitable inorganic or organic acid, such as mineral acids such as HCl, HBr, H2SO4, H3PO4, or HNO3, or organic acids, e.g., carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid, or sulfonic acids such as p-toluenesulfonic acid, to a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino, or pyridino.
  • a suitable inorganic or organic acid such as mineral acids such as HCl, HBr, H2SO4, H3PO4, or HNO3, or organic acids, e.g., carboxylic acids such as formic acid, acetic acid, propionic acid, oxa
  • R X is (C1-C3)-alkyl
  • X is halogen or (C1-C3)-alkyl
  • Y is OCF3 or OCHF2, OCF2Me
  • Z is (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl or (C1-C3)-alkyl-O-(C1-C3)-alkyl
  • n is 0, 1 or 2.
  • R X is Me or Et
  • X is chlorine, bromine, Me or Et
  • Y is OCF3
  • Z is Me, Et, c-Pr, CH2 -c-Pr or ( CH2 ) 2OMe
  • n means 0, 1 or 2.
  • the present invention thus further relates to compounds of formula (II), where the symbols and indices have the following meanings: L means halogen or R 2 O, X is halogen or (C1-C6)-alkyl, Y is halogen-(C1-C6)-alkoxy, Z is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl or (C1-C6)-alkyl-O-(C1-C6)-alkyl, R2 is hydrogen or (C1-C6)-alkyl, and n is 0, 1 or 2.
  • Preferred compounds (II) are those in which L is chlorine, methoxy or hydroxy, X is chlorine, bromine, methyl or ethyl, Y is OCF3 , OCHF2 or OCF2Me , Z is methyl, ethyl, c-propyl, CH2 -c-propyl or ( CH2 ) 2OMe , and n is 0, 1 or 2.
  • L is chlorine, methoxy or hydroxy
  • X is chlorine, bromine, methyl or ethyl
  • Y is OCF3 , OCHF2 or OCF2Me
  • Z is methyl, ethyl, c-propyl, CH2 -c-propyl or ( CH2 ) 2OMe
  • n is 0, 1 or 2.
  • a range of commercially available devices can be used for parallelized reaction execution and workup, for example Calpyso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Massachusetts 02451, USA.
  • chromatography apparatus is available, for example from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. The listed apparatus lead to a modular procedure in which the individual work steps are automated, but manual operations must be carried out between the work steps.
  • the present invention therefore also provides a method for controlling undesirable plants or for regulating the growth of plants, preferably in plant crops, in which one or more compounds according to the invention are applied to the plants (e.g. weeds such as mono- or dicotyledonous weeds or undesirable crop plants), the seed (e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds) or the area on which the plants are growing (e.g. the cultivated area).
  • the compounds according to the invention can be applied, for example, by pre-sowing (optionally also by incorporation into the soil), pre-emergence or post-emergence.
  • Monocotyledonous weeds of the genera Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum.
  • the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, are only insignificantly damaged or not damaged at all, depending on the structure of the respective compound according to the invention and the application rate thereof.
  • the present compounds are highly suitable for the selective control of undesirable plant growth in plant crops such as agricultural crops or ornamental plants.
  • the compounds according to the invention depending on their respective chemical structure and the application rate, exhibit outstanding growth-regulating properties in crops. They regulate the plant's own metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, for example by inducing desiccation and stunting.
  • they are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, since, for example, lodging can be reduced or completely prevented as a result.
  • the active ingredients can also be used to control weeds in crops of plants modified genetically or by conventional mutagenesis.
  • the transgenic plants are usually characterized by particularly advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens from plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate, for example, to the harvested product in terms of quantity, quality, storability, composition and special ingredients. For example, transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition of the harvested product are known.
  • transgenic crops With regard to transgenic crops, the use of the compounds according to the invention is preferred in economically important transgenic crops of useful and ornamental plants, e.g. cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, cassava, tomatoes, peas and other vegetables.
  • the compounds according to the invention can preferably be used as herbicides in useful plant crops that are resistant to the phytotoxic effects of the herbicides or have been genetically engineered to be resistant. Conventional ways of producing new plants that have modified properties compared to previously occurring plants consist, for example, in classic breeding methods and the generation of mutants.
  • new plants with modified characteristics can be produced using genetic engineering techniques (see, for example, EP-A-0221044, EP-A-0131624).
  • genetic engineering techniques see, for example, EP-A-0221044, EP-A-0131624.
  • the following have been described in several cases: - genetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827, WO 91/19806), - transgenic crop plants which are resistant to certain herbicides of the glufosinate type (cf. e.g.
  • Bt toxins Bacillus thuringiensis toxins
  • EP-A-0193259 Bacillus thuringiensis toxins
  • - Transgenic crops with modified fatty acid composition WO 91/13972.
  • Genetically modified crops with new ingredients or secondary substances, e.g., new phytoalexins, that cause increased disease resistance EPA 309862, EPA0464461).
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence modification through recombination of DNA sequences.
  • base exchanges can be performed, partial sequences can be removed, or natural or synthetic sequences can be added.
  • adapters or linkers can be attached to the fragments, see e.g. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones", VCH Weinheim 2nd ed.
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one correspondingly constructed ribozyme that specifically cleaves transcripts of the above-mentioned gene product.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, or DNA molecules that comprise only parts of the coding sequence, whereby these parts must be long enough to produce an antisense effect in the cells. It is also possible to use DNA sequences that have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein can be localized in any compartment of the plant cell.
  • the coding region can, for example, be linked to DNA sequences that ensure localization in a specific compartment.
  • sequences are known to the person skilled in the art (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).
  • Expression of the nucleic acid molecules can also take place in the organelles of plant cells.
  • the transgenic plant cells can be regenerated into whole plants using known techniques.
  • transgenic plants can, in principle, be plants of any plant species, i.e., both monocotyledonous and dicotyledonous plants.
  • the compounds according to the invention can preferably be used in transgenic crops that are resistant to growth promoters, such as dicamba, or to herbicides that inhibit essential plant enzymes, e.g., acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS), or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates, or benzoyl isoxazoles and analogous active ingredients.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydroxyphenylpyruvate dioxygenases
  • the active compounds according to the invention are used in transgenic crops, in addition to the effects on weeds observed in other crops, effects often occur which are specific to the application in the respective transgenic crop, for example a modified or specifically expanded weed spectrum that can be controlled, modified application rates that can be used for application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing the growth and yield of the transgenic crops.
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling weeds in transgenic crops.
  • the compounds according to the invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary preparations.
  • the invention therefore also relates to herbicidal and plant growth regulating compositions which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on the biological and/or chemical-physical parameters specified. Possible formulation options 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-miscible solutions, capsule suspensions (CS), dusts (DP), seed dressings, granules for broadcast and soil application, granules (GR) in the form of microgranules, spray granules, emulsifiable granules, and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG
  • Wettable powders are preparations that are evenly dispersible in water and which, in addition to the active ingredient and a diluent or inert substance, also contain ionic and/or non-ionic surfactants (wetting agents, dispersants), e.g.
  • the herbicidal active ingredients are finely ground in conventional equipment such as hammer mills, fan mills, and air jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g., butanol, cyclohexanone, dimethylformamide, xylene, or higher-boiling aromatics or hydrocarbons, or mixtures of these organic solvents, with the addition of one or more ionic and/or non-ionic surfactants (emulsifiers).
  • organic solvent e.g., butanol, cyclohexanone, dimethylformamide, xylene, or higher-boiling aromatics or hydrocarbons, or mixtures of these organic solvents.
  • emulsifiers examples include: alkylarylsulfonic acid calcium salts such as Ca dodecylbenzenesulfonate or non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters. Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g.
  • Suspension concentrates can be water- or oil-based. They can be produced, for example, by wet grinding using commercially available bead mills and, if necessary, with the addition of surfactants, such as those listed above for the other formulation types.
  • Emulsions e.g. oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • Granules can be produced either by spraying the active ingredient onto adsorptive, granulated inert material or by applying active ingredient concentrates using adhesives, e.g. polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules - if desired in a mixture with fertilizers. Water-dispersible granules are generally produced using conventional processes such as spray drying, fluidized bed granulation, disc granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds according to the invention.
  • the active ingredient concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consisting of conventional formulation components.
  • the active ingredient concentration can be about 1 to 90, preferably 5 to 80% by weight.
  • Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably 5 to 20% by weight of active ingredient, and sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends partly on whether the active compound is in liquid or solid form and on which granulation aids, fillers, etc. are used.
  • the active ingredient content is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetrating agents, preservatives, antifreeze agents, solvents, fillers, Carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and viscosity.
  • combinations with other pesticidally active substances such as insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and/or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix.
  • the formulations available in commercial form are diluted in the usual way if necessary, e.g.
  • the required application rate of the compounds of the formula (I) varies with external conditions such as temperature, humidity and the type of herbicide used, among other factors. It can vary within wide limits, e.g., between 0.001 and 1.0 kg/ha or more of active ingredient, but is preferably between 0.005 and 750 g/ha.
  • the compounds of formula (I) according to the invention can also be used as a mixture with other herbicides, if required.
  • herbicides or plant growth regulators which can be combined with compounds of formula (I) include, for example, the following active ingredients (the compounds are designated either by the "common name” according to the International Organization for Standardization (ISO) or by the chemical name or by the code number) and always include all application forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • Acetochlor Acifluorfen, Acifluorfen-methyl, Acifluorfen-sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazon, 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, Amitrol, Ammonium sulfamate, Anilofos, Asulam, Asulam-potassium, Asulam- Sodium, atrazine, azafenidine, azimsulfur
  • dicamba biproamine dicamba N,N-bis(3-aminopropyl)methylamine, dicamba butotyl, dicamba choline, dicamba diglycolamine, dicamba Dimethylammonium, Dicamba-Diethanolaminemmonium, Dicamba-Diethylammonium, Dicamba-isopropylammonium, Dicamba-methyl, Dicamba-monoethanolamine, Dicamba-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, dichlorprop-dimethylammonium, dichlorprop-etexyl, dichlorprop-eth
  • Abscisic acid and related analogues [e.g. (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid, methyl-(2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoic acid, methyl (2E
  • COs differ from LCOs in that they lack the fatty acid side chain characteristic of LCOs.
  • COs sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units, but have side chains that distinguish them from chitin molecules [(C8H13NO5)n, CAS No. 1398-61-4] and chitosan molecules [(C5H11NO4)n, CAS No.
  • LCO lipochitooligosaccharides
  • Nod or Nod factors symbiotic nodulation signals
  • Myc factors consist of an oligosaccharide backbone of ⁇ -l,4-linked N-acetyl-D-glucosamine residues (“GlcNAc”) with an N-linked fatty acid side chain fused to the non-reducing end.
  • LCOs differ in the number of GlcNAc units in the backbone structure, in the length and degree of saturation of the fatty acid chain as well as in the substitution of the reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic acid hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-Methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-( ⁇ [(2R)-4-methyl-5-ox
  • Safeners that can be used in combination with the compounds of formula (I) according to the invention and optionally in combination with other active ingredients such as insecticides, acaricides, herbicides, fungicides as listed above are preferably selected from the group consisting of: S1) compounds of formula (S1), where the symbols and indices have the following meanings: n A is a natural number from 0 to 5, preferably 0 to 3; RA 1 is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl; N WA is an unsubstituted or substituted divalent heterocyclic radical from the group of the partially saturated or aromatic five-membered ring heterocycles having 1 to 3 hetero ring atoms from the group N and O, wherein at least one N atom and at most one O atom is contained
  • RC 1 is (C1-C4)alkyl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C3-C7)cycloalkyl, preferably dichloromethyl;
  • RC 2 , RC 3 are identical or different and are hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C1-C4)haloalkyl, (C2-C4)haloalkenyl, (C1-C4)alkylcarbamoyl-(C1-C4)alkyl, (C2-C4)alkenylcarbamoyl-(C1-C4)alkyl, (C1-C4)alkoxy-(C1-C4)alkyl, dioxolanyl-(C1-C4)alkyl, thi
  • X D is CH or N
  • RD 1 is CO-NRD 5 RD 6 or NHCO-RD 7
  • RD 2 is halogen, (C1-C4)haloalkyl, (C1-C4)haloalkoxy, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylsulfonyl, (C1-C4)alkoxycarbonyl or (C1-C4)alkylcarbonyl
  • RD 3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl
  • RD 4 is halogen, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, (C3-
  • RD 7 is (C1-C6)alkyl, (C3-C6)cycloalkyl, the last two radicals being substituted by vD substituents from the group halogen, (C1-C4)alkoxy, (C1-C6)haloalkoxy and (C1-C4)alkylthio and, in the case of cyclic radicals, also (C1-C4)alkyl and (C1-C4)haloalkyl; RD 4 is halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3; mD is 1 or 2; vD is 0, 1, 2 or 3; and acylsulfamoylbenzoic acid amides, e.g.
  • S5 Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.
  • S6 Active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g.
  • Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones e.g. 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020.
  • R G 1 is halogen, (C 1 -C 4 )alkyl, methoxy, nitro, cyano, CF 3 , OCF 3 Y G , Z G independently of one another is O or S
  • n G is an integer from 0 to 4
  • R G 2 is (C 1 -C 16 )alkyl, (C 2 -C 6 )alkenyl, (C 3 -C 6 )cycloalkyl, aryl; benzyl, halobenzyl, R G 3 is hydrogen or (C 1 -C 6 )alkyl.
  • S11 Active ingredients of the oxyimino compound type (S11), which are known as seed dressing agents, such as, for example, B.
  • “Oxabetrinil” ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet against metolachlor damage
  • "Fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2), which is known as a seed dressing safener for millet against metolachlor damage
  • “Cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet against metolachlor
  • S12 Active ingredients from the class of isothiochromanones (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361.
  • S12 isothiochromanones
  • S13 One or more compounds from group (S13): “Naphthalic anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides, "Fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is used as a safener for pretilachlor in sown rice, “Flurazole” (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for millet against damage from alachlor and metolachlor, "CL 304415” (CAS Reg.
  • Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor, dichlormid and metcamifen.
  • the following examples illustrate the invention. A.
  • Step 1 Preparation of 1-bromo-2-chloro-3-methyl-4-(trifluoromethoxy)benzene (4): 20.35 ml (145.2 mmol) of diisopropylamine were placed in 250 ml of tetrahydrofuran under argon, and 79.4 ml (127.1 mmol) of n-butyllithium (1.6 M solution in hexane) were added dropwise at -60 ° C, and the solution was stirred for 1 h.
  • Step 2 Preparation of 2-chloro-3-methyl-4-(trifluoromethoxy)benzonitrile (5): 18.91 g (65.33 mmol) of 1-bromo-2-chloro-3-methyl-4-(trifluoromethoxy)benzene (4) was dissolved in 150 ml of dimethylformamide, and 11.7 g (130.65 mmol) of copper(I) cyanide was added at room temperature. The resulting reaction mixture was heated to reflux for 12 h. It was then poured into 1 l of cold water and treated with ethyl acetate. After vigorous stirring for 10 min, the mixture was filtered and the phases were separated. The organic phase was dried and evaporated.
  • Step 3 Preparation of 2-chloro-3-methyl-4-(trifluoromethoxy)benzoic acid (6): 10.92 g (46.35 mmol) of 2-chloro-3-methyl-4-(trifluoromethoxy)benzonitrile (5) were dissolved in a solution of 17.73 g (443 mmol) of sodium hydroxide in 180 ml of water and heated to reflux for 6 h. The mixture was then left to stand overnight at room temperature. The mixture was then washed with dichloromethane and the aqueous phase was adjusted to pH 1 with 2 M hydrochloric acid. The mixture was then extracted with ethyl acetate and the organic phase was separated, dried and evaporated.
  • Step 4 Preparation of methyl 2-chloro-3-methyl-4-(trifluoromethoxy)benzoate (7): 22.08 g (86.73 mmol) of 2-chloro-3-methyl-4-(trifluoromethoxy)benzoic acid (6) were initially dissolved in 400 ml of dichloromethane and 3 ml of dimethylformamide, and 11.58 ml (13.09 mmol) of oxalyl chloride were slowly added at room temperature. The mixture was then stirred for 1 h at room temperature. After 20 ml (1734.5 mmol) of methanol was added dropwise, the mixture was stirred for 3 h at room temperature, and the solution was evaporated to dryness.
  • Step 5 Preparation of methyl 3-(bromomethyl)-2-chloro-4-(trifluoromethoxy)benzoate (1): 10.42 g (38.79 mmol) of methyl 2-chloro-3-methyl-4-(trifluoromethoxy)benzoate (7) were dissolved in 100 g of chlorobenzene, and 13.81 g (77.58 mmol) of N-bromosuccinimide and 0.64 g (3.88 mmol) of AIBN were added. The reaction mixture was stirred at 120 ° C for 8 h. It was then evaporated, and the residue was taken up in water and extracted with dichloromethane. The organic phase was separated, dried, and evaporated.
  • Step 1 Preparation of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (9): 10 g (47.35 mmol) of commercially available methyl 2-chloro-4-hydroxy-3-methylbenzoate (8) were added portionwise to a solution of 19.93 g of potassium hydroxide in 75 ml of acetonitrile and 75 ml of water at 0 ° C.
  • Step 2 Preparation of methyl 3-(bromomethyl)-2-chloro-4-(difluoromethoxy)benzoate (2): 20.65 g (82.39 mmol) of methyl 2-chloro-4-(difluoromethoxy)-3-methylbenzoate (9) was dissolved in 200 g of chlorobenzene, and 29.33 g (164.79 mmol) of N-bromosuccinimide and 1.35 g (8.24 mmol) of AIBN were added.
  • Step 2 Preparation of 2-chloro-3-[(methylsulfanyl)methyl]-4-(trifluoromethoxy)benzoic acid (4-31): 2.15 g (6.83 mmol) of methyl 2-chloro-3-[(methylsulfanyl)methyl]-4-(trifluoromethoxy)benzoate (3-31) were initially charged in 100 ml of methanol, and 6.83 ml (13.66 mmol) of 2M sodium hydroxide solution was added at room temperature. The reaction mixture was stirred for 12 h at room temperature and then evaporated. The residue was taken up with water, and the aqueous phase was adjusted to pH 1 with 2M hydrochloric acid. The organic phase was separated, dried, and evaporated.
  • Step 3 Preparation of 2-chloro-3-[(methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-31): 600 mg (2 mmol) of 2-chloro-3-[(methylsulfanyl)methyl]-4-(trifluoromethoxy)benzoic acid (4-31) and 302.7 mg (3 mmol) of 5-amino-1-methyl-1H-tetrazole were initially charged in 10 ml of pyridine, and 0.27 ml (3 mmol) of oxalyl chloride was added dropwise at room temperature.
  • Step 4 Preparation of (R,S)-2-chloro-3-[(methylsulfinyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-32): 68 mg (0.17 mmol) of 2-chloro-3-[(methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethoxy)benzamide (1-31) were initially charged in 3 ml of glacial acetic acid, and 0.016 ml (0.17 mmol) of a 25% aqueous hydrogen peroxide solution was added at room temperature. The mixture was stirred at 60 ° C for 4 h.
  • Table 2 Compounds of the formula (I) according to the invention, wherein R x represents an ethyl group and the other substituents have the meanings given below.
  • N Table 3: Compounds of the formula (II) according to the invention, wherein L is methoxy and the other substituents have the meanings given below,
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and/or its salts and 90 parts by weight of talc as an inert substance and grinding the mixture in a hammer mill.
  • a wettable powder that is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of formula (I) and/or its salts, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium ligninsulfonate, and 1 part by weight of sodium oleoylmethyltaurine as wetting and dispersing agents, and grinding the mixture in a pin-type mill.
  • a dispersion concentrate which is easily dispersible in water is obtained by mixing 20 parts by weight of a compound of formula (I) and/or its salts with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, approx. 255 to over 277 °C) and grinding in a ball mill to a fineness of less than 5 microns.
  • alkylphenol polyglycol ether ®Triton X 207
  • isotridecanol polyglycol ether 8 EO
  • paraffinic mineral oil oil
  • grinding range for example, approx. 255 to over 277 °C
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I) and/or its salts, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • Water-dispersible granules are obtained by mixing 75 parts by weight of a compound of formula (I) and/or its salts, 10 parts by weight of calcium ligninsulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol, and 7 parts by weight of kaolin, grinding the mixture on a pin mill, and granulating the powder in a fluidized bed by spraying water as the granulating liquid.
  • Water-dispersible granules are also obtained by mixing 25 parts by weight of a compound of formula (I) and/or its salts, 5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, 2 parts by weight of oleoylmethyltauric acid sodium, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water are homogenized and pre-crushed in a colloid mill, then ground in a bead mill and the resulting suspension is atomized and dried in a spray tower using a single-component nozzle.
  • a compound of formula (I) and/or its salts 5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, 2 parts by weight of oleoylmethyltauric acid sodium, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water
  • weeds mean: ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AVEFA Avena fatua AMARE Amaranthus retroflexus CYPES Cyperus esculentus DIGSA Digitaria sanguinalis ECHCG Echinochloa crus-galli HORMU Hordeum murinum KCHSC Kochia scoparia LOLMU Lolium multiflorum LOLRI Lolium rigidum MATIN Matricaria inodora PHBPU Pharbitis purpurea POLCO Polygonum convolvulus SETVI Setaria viridis STEME Stellaria media VERPE Veronica persica VIOTR Viola tricolor 1.
  • Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants are placed in sandy loam soil in wood fibre pots and covered with soil.
  • the compounds of the invention formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then applied to the surface of the covering soil as an aqueous suspension or emulsion at a water application rate of the equivalent of 600 to 800 l/ha with the addition of 0.2% wetting agent. After treatment, the pots are placed in the greenhouse and maintained under favorable growth conditions for the test plants.
  • WP wettable powders
  • EC emulsion concentrates
  • Table C-8 Pre-emergence effect at 80g/ha against ALOMY in %
  • Table C-9 Pre-emergence effect at 20g/ha against AMARE in %
  • Table C-10 Pre-emergence effect at 80g/ha against AMARE in %
  • Table C-17 Pre-emergence effect at 80g/ha against MATIN in %
  • Table C-18 Pre-emergence effect at 80g/ha against PHBPU in %
  • Table C-19 Pre-emergence effect at 20g/ha against POLCO in %
  • Table C-20 Pre-emergence effect at 80g/ha against POLCO in %
  • Table C-27 Pre-emergence effect at 20g/ha against KCHSC in %
  • Table C-28 Pre-emergence effect at 80g/ha against KCHSC in % 2.
  • Post-emergence herbicidal activity against weeds Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants are sown in wood-fiber pots in sandy loam soil, covered with soil, and grown in a greenhouse under favorable growth conditions. Two to three weeks after sowing, the test plants are treated at the single-leaf stage.
  • the compounds of the invention formulated as wettable powders (WP) or emulsion concentrates (EC), are then applied to the green leaves as an aqueous suspension or emulsion at a water application rate of the equivalent of 600 to 800 l/ha, with the addition of 0.2% wetting agent. Plant parts were sprayed.
  • Table C-29 Postemergence activity at 20 e en ZEAMX /ha in %
  • Table C-35 Post-emergence effect at 80g/ha against ALOMY in %
  • Table C-36 Post-emergence effect at 20g/ha against AMARE in %
  • Table C-37 Post-emergence effect at 80g/ha against AMARE in %
  • Table C-44 Post-emergence effect at 80g/ha against PHBPU in %
  • Table C-45 Post-emergence effect at 80g/ha against POLCO in %
  • Table C-46 Post-emergence effect at 20g/ha against SETVI in % I
  • Table C-47 Post-emergence effect at 80g/ha against SETVI in %
  • Table C-48 Post-emergence effect at 20/ha a VERPE in %
  • Table C-53 Post-emergence effect at 80g/ha against KCHSC in % Comparative Experiments
  • the herbicidal activity of numerous compounds according to the invention and the structurally closest compounds known from WO2020/148175
  • V-1 2-chloro-4-methoxy-3-[(methylsulfanyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)benzamide
  • V-2 (R,S)-2-chloro-4-methoxy-3-[(methylsulfinyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)benzamide
  • V-3 2-chloro-4-methoxy-3-[(methylsulfonyl)methyl]-N-(1-methyl-1H-tetrazol-5-yl)benzamide
  • V-4 2-chloro-N-(1-ethyl-1H-tetrazol-5-yl)-4-methoxy-3-[(methylsulfanyl)methyl]benzamide

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Abstract

L'invention concerne des arylcarboxamides de formule (I) en tant qu'herbicides. Dans la formule (I), X, Y, Z et Rx sont des groupes tels qu'alkyle, cycloalkyle, halogénoalkyle et halogène.
PCT/EP2024/083582 2023-11-29 2024-11-26 Arylcarboxamides substitués Pending WO2025114265A1 (fr)

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Citations (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2906507A1 (de) 1979-02-20 1980-08-28 Bayer Ag Mittel zur regulierung des pflanzenwachstums
EP0030287A1 (fr) 1979-11-29 1981-06-17 Bayer Ag Dérivés de l'acide amino-1 cyclopropanecarboxylique, procédés pour leur préparation, leur utilisation comme régulateurs de la croissance de végétaux et compositions contenant de tels dérivés
EP0086750A2 (fr) 1982-02-17 1983-08-24 Ciba-Geigy Ag Utilisation de dérivés de la quinoléine pour la protection de plantes cultivables
EP0094349A2 (fr) 1982-05-07 1983-11-16 Ciba-Geigy Ag Utilisation de dérivés de quinoléine pour protéger des plantes cultivées
EP0131624A1 (fr) 1983-01-17 1985-01-23 Monsanto Co Plasmides de transformation de cellules vegetales.
DE3335514A1 (de) 1983-09-30 1985-04-18 Bayer Ag, 5090 Leverkusen 1-methylamino-cyclopropan-1-carbonsaeure-derivate
JPS6087254A (ja) 1983-10-19 1985-05-16 Japan Carlit Co Ltd:The 新規尿素化合物及びそれを含有する除草剤
EP0142924A2 (fr) 1983-09-26 1985-05-29 Mycogen Plant Science, Inc. Plantes resistantes aux insectes
EP0174562A2 (fr) 1984-09-11 1986-03-19 Hoechst Aktiengesellschaft Agents pour la protection de plantes basés sur des dérivés de 1,2,4- briazole ainsi que dérivés 1,2,4-triazole
EP0191736A2 (fr) 1985-02-14 1986-08-20 Ciba-Geigy Ag Utilisation de dérivés de la quinoléine pour la protection de plantes cultivables
EP0193259A1 (fr) 1985-01-18 1986-09-03 Plant Genetic Systems N.V. Modification des plantes par une méthode de génie génétique pour combattre ou contrôler des insectes
EP0221044A1 (fr) 1985-10-25 1987-05-06 Monsanto Company Vecteurs de plantes
EP0242236A1 (fr) 1986-03-11 1987-10-21 Plant Genetic Systems N.V. Cellules végétales résistantes aux inhibiteurs de la synthétase de glutamine, produites par génie génétique
EP0257993A2 (fr) 1986-08-26 1988-03-02 E.I. Du Pont De Nemours And Company Fragment d'acide nucléique codant la synthase acétolactate végétale résistante aux herbicides
EP0268554A2 (fr) 1986-10-22 1988-05-25 Ciba-Geigy Ag Dérivés d'acide diphényl-1,5-pyrazol-3-carbonique pour la protection de plantes de culture
EP0269806A1 (fr) 1986-10-04 1988-06-08 Hoechst Aktiengesellschaft Dérivés d'acide phénylpyrazolcarbonique, leur préparation et leur utilisation comme agents régulateurs de croissance des plantes et antidote
EP0333131A1 (fr) 1988-03-17 1989-09-20 Hoechst Aktiengesellschaft Agent de protection des plantes à base de dérivés d'acide pyrazolcarboxylique
EP0346620A1 (fr) 1988-05-20 1989-12-20 Hoechst Aktiengesellschaft Agents phytoprotecteurs contenant des dérivés du 1,2,4-triazole ainsi que dérivés du 1,2,4-triazole
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
WO1991008202A1 (fr) 1989-11-25 1991-06-13 Hoechst Aktiengesellschaft Isoxazolines, procede de preparation et application comme produits phytosanitaires
WO1991007874A1 (fr) 1989-11-30 1991-06-13 Hoechst Aktiengesellschaft Pyrazoline pour la protection de plantes cultivees contre les herbicides
WO1991013972A1 (fr) 1990-03-16 1991-09-19 Calgene, Inc. Desaturases de plantes - compositions et emplois
WO1991019806A1 (fr) 1990-06-18 1991-12-26 Monsanto Company Plantes a teneur en amidon augmentee
WO1992000377A1 (fr) 1990-06-25 1992-01-09 Monsanto Company Plantes tolerant le glyphosate
US5123951A (en) 1986-03-31 1992-06-23 Rhone-Poulenc Nederland B.V. Synergistic plant growth regulator compositions
EP0492366A2 (fr) 1990-12-21 1992-07-01 Hoechst Schering AgrEvo GmbH Nouveaux dérivés de chloro-5-quinoline-8-acide oxyalkanecarboniques, procédé pour leur préparation et leur utilisation comme antidote d'herbicides
WO1992011376A1 (fr) 1990-12-21 1992-07-09 Amylogene Hb Modification de la pomme de terre par manipulation genetique permettant la formation de fecule du type amylopectine
WO1992014827A1 (fr) 1991-02-13 1992-09-03 Institut Für Genbiologische Forschung Berlin Gmbh Plasmides contenant des sequences d'adn provoquant des changements dans la concentration et la composition glucidiques de plantes, cellules de plantes et plantes contenant ces plasmides
EP0582198A2 (fr) 1992-08-01 1994-02-09 Hoechst Schering AgrEvo GmbH Composés (hétéro-)aryliques substitués, procédé pour leur préparation, compositions les contenant et leur utilisation comme agents de protection
WO1995007897A1 (fr) 1993-09-16 1995-03-23 Hoechst Schering Agrevo Gmbh Isoxazolines substituees, leur procede de preparation, agents les contenant et leur utilisation comme reducteurs de phytotoxicite
WO1997045016A1 (fr) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh Nouveaux n-acylsulfonamides, nouveaux melanges d'herbicides et d'antidotes et leur utilisation
WO1998013361A1 (fr) 1996-09-26 1998-04-02 Novartis Ag Composition herbicide
WO1998027049A1 (fr) 1996-12-19 1998-06-25 Hoechst Schering Agrevo Gmbh Nouveaux derives d'acide 2-fluoroacrylique, nouveaux melanges d'herbicides et d'antidotes et leur utilisation
WO1998038856A1 (fr) 1997-03-04 1998-09-11 Zeneca Limited Compositions pour proteger du riz contre l'acetochlore
WO1999000020A1 (fr) 1997-06-27 1999-01-07 Hoechst Schering Agrevo Gmbh 3-(5-tetrazolylcarbonyle)-2-quinolones et produits phytosanitaires pour plantes utiles les contenant
WO1999016744A1 (fr) 1997-09-29 1999-04-08 Aventis Cropscience Gmbh Amides d'acide benzoique d'acylsulfamoyle, agents phytosanitaires les contenant et procede permettant de les preparer
WO2002034048A1 (fr) 2000-10-23 2002-05-02 Syngenta Participations Ag Compositions agrochimiques avec des phytoprotecteurs a base de quinoline
WO2004084631A1 (fr) 2003-03-26 2004-10-07 Bayer Cropscience Gmbh Utilisation de composés aromatiques hydroxy comme phytoprotecteurs
WO2005015994A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Utilisation d'aromates hydroxy comme phytoprotecteurs
WO2005016001A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Agents phytoprotecteurs a base de derives d'acide carboxylique aromatiques-aliphatiques
WO2005112630A1 (fr) 2004-05-12 2005-12-01 Bayer Cropscience Gmbh Derives de quinoxalin-2-one, phytoprotecteurs pour plantes utiles contenant ces derives, procede de production et utilisation desdits derives
WO2007023719A1 (fr) 2005-08-22 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent servant à réduire l'attaque chimique et composition herbicide produisant une attaque chimique réduite
WO2007023764A1 (fr) 2005-08-26 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent servant à réduire les effets nocifs d’un herbicide et composition d’herbicide ayant des effets nocifs réduits
WO2008131861A1 (fr) 2007-04-30 2008-11-06 Bayer Cropscience Ag Utilisation de pyridin-2-oxy-3-carbonamides comme phytoprotecteurs
WO2008131860A2 (fr) 2007-04-30 2008-11-06 Bayer Cropscience Ag Pyridone-carboxamides, phytoprotecteurs contenant ces composés, procédés pour leur production et leur utilisation
EP2248421A1 (fr) 2009-05-07 2010-11-10 GMI - Gregor-Mendel-Institut für Molekulare Pflanzenbiologie GmbH Accumulation de biomasse dans les plantes
WO2012028579A1 (fr) 2010-09-01 2012-03-08 Bayer Cropscience Ag Amides de l'acide n-(tétrazol-5-yl)- et n-(triazol-5-yl)arylcarboxylique, et leur utilisation comme herbicides
WO2020148175A1 (fr) 2019-01-14 2020-07-23 Bayer Aktiengesellschaft N-tétrazolylarylcarboxamides substitués herbicides
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
US20220402882A1 (en) * 2019-11-15 2022-12-22 Syngenta Crop Protection Ag Herbicidal compounds
WO2023066784A1 (fr) * 2021-10-20 2023-04-27 Syngenta Crop Protection Ag Benzamides substitués utilisés en tant qu'herbicides

Patent Citations (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2906507A1 (de) 1979-02-20 1980-08-28 Bayer Ag Mittel zur regulierung des pflanzenwachstums
EP0030287A1 (fr) 1979-11-29 1981-06-17 Bayer Ag Dérivés de l'acide amino-1 cyclopropanecarboxylique, procédés pour leur préparation, leur utilisation comme régulateurs de la croissance de végétaux et compositions contenant de tels dérivés
EP0086750A2 (fr) 1982-02-17 1983-08-24 Ciba-Geigy Ag Utilisation de dérivés de la quinoléine pour la protection de plantes cultivables
EP0094349A2 (fr) 1982-05-07 1983-11-16 Ciba-Geigy Ag Utilisation de dérivés de quinoléine pour protéger des plantes cultivées
EP0131624A1 (fr) 1983-01-17 1985-01-23 Monsanto Co Plasmides de transformation de cellules vegetales.
EP0142924A2 (fr) 1983-09-26 1985-05-29 Mycogen Plant Science, Inc. Plantes resistantes aux insectes
DE3335514A1 (de) 1983-09-30 1985-04-18 Bayer Ag, 5090 Leverkusen 1-methylamino-cyclopropan-1-carbonsaeure-derivate
JPS6087254A (ja) 1983-10-19 1985-05-16 Japan Carlit Co Ltd:The 新規尿素化合物及びそれを含有する除草剤
EP0174562A2 (fr) 1984-09-11 1986-03-19 Hoechst Aktiengesellschaft Agents pour la protection de plantes basés sur des dérivés de 1,2,4- briazole ainsi que dérivés 1,2,4-triazole
EP0193259A1 (fr) 1985-01-18 1986-09-03 Plant Genetic Systems N.V. Modification des plantes par une méthode de génie génétique pour combattre ou contrôler des insectes
EP0191736A2 (fr) 1985-02-14 1986-08-20 Ciba-Geigy Ag Utilisation de dérivés de la quinoléine pour la protection de plantes cultivables
EP0221044A1 (fr) 1985-10-25 1987-05-06 Monsanto Company Vecteurs de plantes
EP0242236A1 (fr) 1986-03-11 1987-10-21 Plant Genetic Systems N.V. Cellules végétales résistantes aux inhibiteurs de la synthétase de glutamine, produites par génie génétique
EP0242246A1 (fr) 1986-03-11 1987-10-21 Plant Genetic Systems N.V. Cellules végétales résistantes aux inhibiteurs de la synthétase de glutamine, produites par génie génétique
US5123951A (en) 1986-03-31 1992-06-23 Rhone-Poulenc Nederland B.V. Synergistic plant growth regulator compositions
EP0257993A2 (fr) 1986-08-26 1988-03-02 E.I. Du Pont De Nemours And Company Fragment d'acide nucléique codant la synthase acétolactate végétale résistante aux herbicides
EP0269806A1 (fr) 1986-10-04 1988-06-08 Hoechst Aktiengesellschaft Dérivés d'acide phénylpyrazolcarbonique, leur préparation et leur utilisation comme agents régulateurs de croissance des plantes et antidote
EP0268554A2 (fr) 1986-10-22 1988-05-25 Ciba-Geigy Ag Dérivés d'acide diphényl-1,5-pyrazol-3-carbonique pour la protection de plantes de culture
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
EP0333131A1 (fr) 1988-03-17 1989-09-20 Hoechst Aktiengesellschaft Agent de protection des plantes à base de dérivés d'acide pyrazolcarboxylique
EP0346620A1 (fr) 1988-05-20 1989-12-20 Hoechst Aktiengesellschaft Agents phytoprotecteurs contenant des dérivés du 1,2,4-triazole ainsi que dérivés du 1,2,4-triazole
WO1991008202A1 (fr) 1989-11-25 1991-06-13 Hoechst Aktiengesellschaft Isoxazolines, procede de preparation et application comme produits phytosanitaires
WO1991007874A1 (fr) 1989-11-30 1991-06-13 Hoechst Aktiengesellschaft Pyrazoline pour la protection de plantes cultivees contre les herbicides
WO1991013972A1 (fr) 1990-03-16 1991-09-19 Calgene, Inc. Desaturases de plantes - compositions et emplois
WO1991019806A1 (fr) 1990-06-18 1991-12-26 Monsanto Company Plantes a teneur en amidon augmentee
WO1992000377A1 (fr) 1990-06-25 1992-01-09 Monsanto Company Plantes tolerant le glyphosate
EP0492366A2 (fr) 1990-12-21 1992-07-01 Hoechst Schering AgrEvo GmbH Nouveaux dérivés de chloro-5-quinoline-8-acide oxyalkanecarboniques, procédé pour leur préparation et leur utilisation comme antidote d'herbicides
WO1992011376A1 (fr) 1990-12-21 1992-07-09 Amylogene Hb Modification de la pomme de terre par manipulation genetique permettant la formation de fecule du type amylopectine
WO1992014827A1 (fr) 1991-02-13 1992-09-03 Institut Für Genbiologische Forschung Berlin Gmbh Plasmides contenant des sequences d'adn provoquant des changements dans la concentration et la composition glucidiques de plantes, cellules de plantes et plantes contenant ces plasmides
EP0582198A2 (fr) 1992-08-01 1994-02-09 Hoechst Schering AgrEvo GmbH Composés (hétéro-)aryliques substitués, procédé pour leur préparation, compositions les contenant et leur utilisation comme agents de protection
WO1995007897A1 (fr) 1993-09-16 1995-03-23 Hoechst Schering Agrevo Gmbh Isoxazolines substituees, leur procede de preparation, agents les contenant et leur utilisation comme reducteurs de phytotoxicite
WO1997045016A1 (fr) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh Nouveaux n-acylsulfonamides, nouveaux melanges d'herbicides et d'antidotes et leur utilisation
WO1998013361A1 (fr) 1996-09-26 1998-04-02 Novartis Ag Composition herbicide
WO1998027049A1 (fr) 1996-12-19 1998-06-25 Hoechst Schering Agrevo Gmbh Nouveaux derives d'acide 2-fluoroacrylique, nouveaux melanges d'herbicides et d'antidotes et leur utilisation
WO1998038856A1 (fr) 1997-03-04 1998-09-11 Zeneca Limited Compositions pour proteger du riz contre l'acetochlore
WO1999000020A1 (fr) 1997-06-27 1999-01-07 Hoechst Schering Agrevo Gmbh 3-(5-tetrazolylcarbonyle)-2-quinolones et produits phytosanitaires pour plantes utiles les contenant
WO1999016744A1 (fr) 1997-09-29 1999-04-08 Aventis Cropscience Gmbh Amides d'acide benzoique d'acylsulfamoyle, agents phytosanitaires les contenant et procede permettant de les preparer
WO2002034048A1 (fr) 2000-10-23 2002-05-02 Syngenta Participations Ag Compositions agrochimiques avec des phytoprotecteurs a base de quinoline
WO2004084631A1 (fr) 2003-03-26 2004-10-07 Bayer Cropscience Gmbh Utilisation de composés aromatiques hydroxy comme phytoprotecteurs
WO2005015994A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Utilisation d'aromates hydroxy comme phytoprotecteurs
WO2005016001A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Agents phytoprotecteurs a base de derives d'acide carboxylique aromatiques-aliphatiques
WO2005112630A1 (fr) 2004-05-12 2005-12-01 Bayer Cropscience Gmbh Derives de quinoxalin-2-one, phytoprotecteurs pour plantes utiles contenant ces derives, procede de production et utilisation desdits derives
WO2007023719A1 (fr) 2005-08-22 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent servant à réduire l'attaque chimique et composition herbicide produisant une attaque chimique réduite
WO2007023764A1 (fr) 2005-08-26 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent servant à réduire les effets nocifs d’un herbicide et composition d’herbicide ayant des effets nocifs réduits
WO2008131861A1 (fr) 2007-04-30 2008-11-06 Bayer Cropscience Ag Utilisation de pyridin-2-oxy-3-carbonamides comme phytoprotecteurs
WO2008131860A2 (fr) 2007-04-30 2008-11-06 Bayer Cropscience Ag Pyridone-carboxamides, phytoprotecteurs contenant ces composés, procédés pour leur production et leur utilisation
EP2248421A1 (fr) 2009-05-07 2010-11-10 GMI - Gregor-Mendel-Institut für Molekulare Pflanzenbiologie GmbH Accumulation de biomasse dans les plantes
WO2012028579A1 (fr) 2010-09-01 2012-03-08 Bayer Cropscience Ag Amides de l'acide n-(tétrazol-5-yl)- et n-(triazol-5-yl)arylcarboxylique, et leur utilisation comme herbicides
WO2020148175A1 (fr) 2019-01-14 2020-07-23 Bayer Aktiengesellschaft N-tétrazolylarylcarboxamides substitués herbicides
US20220402882A1 (en) * 2019-11-15 2022-12-22 Syngenta Crop Protection Ag Herbicidal compounds
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
WO2023066784A1 (fr) * 2021-10-20 2023-04-27 Syngenta Crop Protection Ag Benzamides substitués utilisés en tant qu'herbicides

Non-Patent Citations (21)

* Cited by examiner, † Cited by third party
Title
"Gene Transfer to Plants", 1995, SPRINGER VERLAG BERLIN
"Microwaves in Organic and Medicinal Chemistry", 2005, VERLAG WILEY
"Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis", CHEMFILES, vol. 4, no. 1
"Synthesis, Analysis, Screening", 1999, VERLAG WILEY, article "Combinatorial Chemistry"
BARRY A. BUNIN: "The Combinatorial Index", 1998, VERLAG ACADEMIC PRESS
BRAUN ET AL., EMBO J., vol. 11, 1992, pages 3219 - 3227
G.C. KLINGMAN: "Weed Control as a Science", 1961, JOHN WILEY AND SONS, INC, pages: 81 - 96
H.V. OLPHEN: "Handbook of Insecticide Dust Diluents and Carriers", 1963, J. WILEY & SONS
J.D. FREYERS.A. EVANS: "Weed Control Handbook", 1968, SCIENTIFIC PUBLICATIONS, pages: 101 - 103
J.E. BROWNING: "Chemical and Engineering", vol. Agglomeration, 1967, pages: 147
K. MARTENS: "Handbook", 1979, GOODWIN LTD, article "Spray Drying"
MCCUTCHEON'S: "Encyclopedia of Surface Active Agents", 1964, CHEM. PUBL. CO. INC
no. 133993-74-5
SAMBROOK ET AL.: "Molecular Cloning, A Laboratory Manual", 1989, COLD SPRING HARBOR LABORATORY PRESS, pages: 2
SCHÖNFELDT: "Grenzflächenaktive Äthylenoxidaddukte", 1976, WISS. VERLAGSGESELL
SONNEWALD ET AL., PLANT J, vol. 1, 1991, pages 95 - 106
VERFAHREN: "Spray-Drying Handbook", 1979, G. GOODWIN LTD
WADEVALKENBURG: "Perry's Chemical Engineer's Handbook", 1973, MARCEL DEKKER, pages: 8 - 57
WINNACKER: "Trends in Plant Science", vol. 1, 1996, VCH WEINHEIM, pages: 423 - 431
WINNACKER-KÜCHLER: "Chemische Technologie", vol. 26, 1986, THE BRITISH CROP PROTECTION COUNCIL AND THE ROYAL SOC. OF CHEMISTRY, article "The Pesticide Manual", pages: 441 - 445
WOLTER ET AL., PROC. NATL. ACAD. SCI. USA, vol. 85, 1988, pages 846 - 850

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