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WO2024194026A1 - 4-difluorométhyl benzamides à action herbicide - Google Patents

4-difluorométhyl benzamides à action herbicide Download PDF

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Publication number
WO2024194026A1
WO2024194026A1 PCT/EP2024/055971 EP2024055971W WO2024194026A1 WO 2024194026 A1 WO2024194026 A1 WO 2024194026A1 EP 2024055971 W EP2024055971 W EP 2024055971W WO 2024194026 A1 WO2024194026 A1 WO 2024194026A1
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WO
WIPO (PCT)
Prior art keywords
methyl
alkyl
acid
plants
ethyl
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.)
Ceased
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PCT/EP2024/055971
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German (de)
English (en)
Inventor
Hartmut Ahrens
Ralf Braun
Harald Jakobi
Arnim Köhn
Christian Waldraff
Elisabeth ASMUS
Birgit BOLLENBACH-WAHL
Jan Dittgen
Elmar Gatzweiler
Christopher Hugh Rosinger
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
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Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to CN202480019442.2A priority Critical patent/CN120882703A/zh
Priority to EP24709395.8A priority patent/EP4680598A1/fr
Publication of WO2024194026A1 publication Critical patent/WO2024194026A1/fr
Priority to MX2025010758A priority patent/MX2025010758A/es
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • 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
    • A01N43/82—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 three 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
    • A01P13/02—Herbicides; Algicides selective

Definitions

  • the invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
  • WO 2018/202535 A1 describes herbicidally active benzoic acid amides which differ from one another essentially in the type of heterocyclic substituent. These benzoic acid amides can be substituted in the 2-, 3- and 4-positions of the phenyl ring by a large number of different radicals. However, the benzoic acid amides known from the above-mentioned documents often have an unfavorable profile with regard to their biological properties, such as herbicidal activity, tolerance to crop plants, toxicological and ecotoxicological properties.
  • the object of the present invention is to provide alternative herbicidally active active ingredients.
  • This object is achieved by the benzoic acid amides according to the invention described below, which carry an alkyl group, a cycloalkyl group, a chlorine atom or a bromine atom in the 2-position of the phenyl ring, a sulfur-containing radical in the 3-position, a CHF2 group in the 4-position and an unsubstituted 1,3,4-oxadiazole on the nitrogen atom of the amide group.
  • the present invention thus relates to benzoic acid amides of the formula (I) and their
  • X is (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, chlorine or bromine,
  • R means (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-Ce)-alkyl or (Ci-Ce)-alkyl-
  • 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.
  • Cycloalkyl is a carbocyclic, saturated ring system with three to six carbon atoms, e.g. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • the compounds of formula (I) can exist as stereoisomers depending on the type and linkage of the substituents. For example, if one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers can occur.
  • Stereoisomers can be obtained from the mixtures obtained during production by conventional separation methods, for example by chromatographic separation processes. Stereoisomers can also be prepared selectively 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 formula (I) but are not specifically defined.
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali or alkaline earth metal hydroxides, carbonates and hydrogen carbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium hydrogen carbonate.
  • salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
  • R to R'" each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • alkylsulfonium and alkylsulfoxonium salts such as (Ci-Cr -trialkylsulfonium and (Ci-Cr -trialkylsulfoxonium salts.
  • X is (C1-C4)-alkyl or chlorine
  • R means (Ci-Ce)-alkyl, (Cs-Cej-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C4)-alkyl or (Ci-C j-Alkyl-O-(Ci-C 4 )- alkyl.
  • R means methyl or ethyl.
  • benzoic acid chlorides or the corresponding benzoic acids on which the compounds (I) according to the invention are based can be prepared, for example, by the methods given in WO 2018/202535 A1.
  • the respective reaction mixtures are usually processed using known methods, for example by crystallization, aqueous-extractive processing, chromatographic methods or a combination of these methods.
  • Collections of compounds of formula (I) and/or their salts, which can be synthesized by the above-mentioned reactions, can also be produced in parallel, whereby this can be done manually, partially automated or fully automated. It is possible, for example, to automate the reaction procedure, the processing or the purification of the products or intermediates. Overall, this is understood to mean a procedure such as that described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (editor Günther Jung), Wiley Publishers 1999, on pages 1 to 34.
  • a range of commercially available devices can be used for parallelized reaction execution and work-up, for example Calpyso reaction blocks (Caylpso 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.
  • Calpyso reaction blocks Caylpso reaction blocks
  • reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, England
  • MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Massachusetts 02451, USA.
  • Chromatography equipment is available from, for example, ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
  • the equipment listed leads to a modular approach in which the individual work steps are automated, but manual operations must be carried out between the work steps. This can be avoided by using partially or fully integrated automation systems in which the respective automation modules are operated by robots, for example.
  • Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
  • the preparation of compounds of formula (I) and their salts can be carried out completely or partially by solid-phase-assisted methods.
  • solid-phase-assisted synthesis methods are adequately described in the specialist literature, e.g. Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (editor Günther Jung), Wiley, 1999.
  • the use of solid-phase-assisted synthesis methods allows a series of protocols known from the literature, which in turn can be carried out manually or automatically.
  • the reactions can be carried out, for example, using IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • Preparation according to the processes described here yields compounds of formula (I) and salts thereof in the form of collections of substances called libraries.
  • the present invention also relates to libraries which contain at least two compounds of formula (I) and salts thereof.
  • the compounds according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous annual weeds. Even difficult-to-control perennial weeds which sprout from rhizomes, rootstocks or other permanent organs are well controlled by the active ingredients.
  • the present invention therefore also relates to 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. harmful plants such as monocotyledonous 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 grow (e.g. the cultivation area).
  • the compounds according to the invention can be applied, for example, in the pre-sowing (optionally also by incorporation into the soil), pre-emergence or post-emergence method.
  • some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention are mentioned by way of example, without the mention being intended to be a restriction to certain species.
  • Monocotyledonous harmful plants 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 are applied to the soil surface before germination, either the emergence of weed seedlings is completely prevented or the weeds grow to the cotyledon stage but then cease growth and finally die completely after three to four weeks.
  • the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, e.g. 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 amount applied. For these reasons, the present compounds are very suitable for the selective control of undesirable plant growth in plant
  • the compounds according to the invention have excellent growth-regulating properties in cultivated plants, depending on their respective chemical structure and the amount applied. They regulate the plant's own metabolism and can therefore be used to specifically influence plant ingredients and to facilitate harvesting, for example by triggering desiccation and stunting. They are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as this can reduce or completely prevent lodging, for example.
  • the active ingredients can also be used to control harmful plants in crops of plants modified by genetic engineering or conventional mutagenesis.
  • the transgenic plants are generally characterized by particularly advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties affect the harvested product in terms of quantity, quality, storability, composition and special ingredients.
  • 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 in economically important transgenic crops of useful and ornamental plants, e.g. of 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, is preferred.
  • the compounds according to the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.
  • new plants with modified properties can be created 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.
  • WO 92/11376, WO 92/14827, WO 91/19806 several cases have been described of 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.
  • transgenic crops with modified fatty acid composition WO 91/13972.
  • Transgenic crops that produce pharmaceutically or diagnostically important proteins (“molecular pharming”), transgenic crops that are characterized by higher yields or better quality, transgenic crops that are characterized by a combination of the new properties mentioned above (“gene stacking”).
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence changes through recombination of DNA sequences.
  • base exchanges can be made, partial sequences can be removed, or natural or synthetic sequences can be added.
  • Adapters or linkers can be attached to the fragments to connect the DNA fragments to one another. can be used, see e.g. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd edition Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones", VCH Weinheim 2nd edition 1996
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by expressing at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately 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, as well as DNA molecules that comprise only parts of the coding sequence, whereby these parts must be long enough to cause 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).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated into whole plants using known techniques.
  • the 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 be used in transgenic cultures which are resistant to growth factors such as dicamba or to herbicides which 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 lisoxazoles and analogous active substances.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydroxyphenylpyruvate dioxygenases
  • 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 used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the usual preparations.
  • the invention therefore also relates to herbicidal and plant growth regulating agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and/or chemical-physical parameters are 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), dusting agents (DP), dressing agents, granules for broadcast and soil application, granules (GR) in the form of micro-, spray, coating and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powders
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • wet powders are preparations that can be evenly dispersed 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, blower mills and air jet mills and mixed simultaneously or subsequently with the formulation aids.
  • 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 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 organic solvents.
  • alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or non-ionic emulsifiers
  • 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. talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances e.g. talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • 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, by adding surfactants, such as those already listed above for the other formulation types.
  • Emulsions eg oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if appropriate, surfactants, such as those already listed above for the other formulation types.
  • Granules can be produced either by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates using adhesives, e.g. polyvinyl alcohol, polyacrylic acid sodium or mineral oils, to the surface of carrier materials such as sand, kaolinite or granulated inert material.
  • Suitable active ingredients can also be granulated in the usual way for the production of fertilizer granules - if desired in a mixture with fertilizers.
  • Water-dispersible granules are usually produced by conventional processes such as spray drying, fluid 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 about 10 to 90% by weight, the remainder (100% by weight) consisting of the usual formulation components.
  • the active ingredient concentration can be about 1 to 90, preferably 5 to 80% by weight. Dust-like formulations contain
  • sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and 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.
  • active ingredient formulations mentioned may contain the usual adhesives,
  • combinations with other pesticidally active substances such as insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and/or growth regulators, can also be produced, e.g. in the form of a ready-made formulation or as a tank mix.
  • the formulations in commercial form are diluted in the usual way if necessary, e.g. with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Dust-like preparations, soil or spreading granules and sprayable solutions are usually not diluted with other inert substances before use.
  • the required application rate of the compounds of formula (I) varies with external conditions such as temperature, humidity, the type of herbicide used, etc. It can vary within wide limits, e.g. between 0.001 and 1.0 kg/ha or more of active substance, 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.
  • active ingredients that can be used as combination partners for the compounds of formula (I) in mixture formulations or in tank mixes are known active ingredients that are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase or that act as plant growth regulators, as are known, for example, from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and the literature cited therein.
  • Known herbicides or plant growth regulators that can be combined with compounds of formula (I) include 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.
  • ISO International Organization for Standardization
  • One and sometimes several application forms are mentioned as examples:
  • 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- l,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4 ,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-etexyl, dichlorpropethylammonium, dichlorprop
  • Abscisic acid and related analogues [e.g. (2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6-dimethyl-4- oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoic acid, methyl-(2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6- dimethyl-4-oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(l-hydroxy-2,6,6- trimethyl-4-oxocyclohex-2-en-l-yl)penta-2,4-dienoic acid, (2E,4E)-5-(l-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-dieno
  • 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 [(CSHBNOS) ⁇ CAS NO. 1398-61-4] and chitosan molecules [(C5H11NO CAS No.
  • chitin-like compounds chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-l-enyl)propionic acid, l-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, l-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozide, dazomet, dazomet sodium, n-decanol, dikegulac, dikegulac sodium, endothal, endothal-di-potassium, -di- sodium, and mono(N,N-dimethylalkylammonium), ethephon, l-ethylcyclopropene, flumetralin, flurenol, flurenol-butyl, fluren
  • 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 hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, l-(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-oxo
  • Safeners which 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:
  • nA is a natural number from 0 to 5, preferably 0 to 3;
  • RA 1 is halogen, (Ci-C4)alkyl, (C1-C4)alkoxy, nitro or (Ci-C4)haloalkyl;
  • WA is an unsubstituted or substituted divalent heterocyclic radical from the group of the partially saturated or aromatic five-membered ring heterocycles with 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom is contained in the ring, preferably a radical from the group (WA 1 ) to (WA 5 ), mA is 0 or 1;
  • RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is linked via the N atom to the carbonyl group in (S1) and is unsubstituted or substituted by radicals from the group (C1-C4) alkyl, (C1-C4) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORA 3 , NHRA 4 or N(CH3)2, in particular of the formula ORA 3 ;
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 C atoms;
  • RA 4 is hydrogen, (Ci-Ce)alkyl, (Ci-Ce)alkoxy or substituted or unsubstituted phenyl;
  • RA 5 is H, (Ci -Cs)alkyl, (Ci-Cs)haloalkyl, (Ci-C4)alkoxy(Ci -Cs)alkyl, cyano or COORA 9 , where RA 9 is hydrogen, (Ci-Cs)alkyl, (Ci-Cs)haloalkyl, (Ci-C 4 )alkoxy-(Ci-C 4 )alkyl, (Ci-C 6 )Hydroxyalkyl, (C3-Ci2)cycloalkyl or tri-(Ci-C 4 )alkylsilyl;
  • RA 6 , RA 7 , RA 8 are identical or different and are hydrogen, (Ci-Cs)alkyl, (Ci-Cs)haloalkyl, (C3-Ci2)cycloalkyl or substituted or unsubstituted phenyl;
  • RA 10 is H, (C 3 -C 12 )cycloalkyl, substituted or unsubstituted phenyl or substituted or unsubstituted heteroaryl; preferably: a) compounds of the dichlorophenylpyrazolin-3-carboxylic acid type (Sl a ), preferably compounds such as l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylate (S 1 - 1) ("mefenpyr-diethyl”), and related compounds as described in WO-A-91/07874; b) derivatives of dichlorophenylpyrazolecarboxylic acid (Sl b ), preferably compounds such as ethyl l-(2,4-dichlor
  • RB 1 is halogen, (Ci-C alkyl, (C1-C4) alkoxy, nitro or (Ci-C4)haloalkyl; ns is a natural number from 0 to 5, preferably 0 to 3;
  • RB 2 is ORB 3 , SRB 3 or NRB 3 RB 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is linked via the N atom to the carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (C1-C4) alkyl, (C1-C4) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORB 3 , NHRB 4 or N(CH3)2, in particular of the formula ORB 3 ;
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 C atoms;
  • RB 4 is hydrogen, (Ci-Ce)alkyl, (Ci-Ce)alkoxy or substituted or unsubstituted phenyl;
  • TB is a (Ci or C2)-alkanediyl chain which is unsubstituted or substituted by one or two (Ci-C4)alkyl radicals or by [(C1-C3)-alkoxy]-carbonyl; preferably: a) compounds of the type 8-quinolinoxyacetic acid (S2 a ), preferably (5-chloro-8-quinolinoxy)acetic acid (l-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8- quinolinoxy)acetic acid-(1,3-dimethyl-but-1-yl)ester (S2-2), (5-chloro-8-quinolinoxy)acetic acid-4-allyloxy-butylester (S2-3), (5-chloro-8-quinolinoxy)acetic acid-l-allyloxy-prop-2-ylester (S2-4), (5-chloro-8-quinolinoxy)acetic acid-ethy
  • Rc 1 is (Ci-C 4 )alkyl, (Ci-C 4 )haloalkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 7 )cycloalkyl, preferably dichloromethyl;
  • Rc 2 , Rc 3 are identical or different and are hydrogen, (Ci-C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkynyl, (Ci-C 4 )haloalkyl, (C 2 -C 4 )haloalkenyl, (Ci-C 4 )alkylcarbamoyl-(Ci-C 4 )alkyl, (C 2 - C 4 )alkenylcarbamoyl-(Ci-C 4 )alkyl, (Ci-C 4 )alkoxy-(Ci-C 4 )alkyl, dioxolanyl-(Ci-C 4 )alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted
  • XD is CH or N
  • RD 1 is CO-NR D 5 RD 6 or NHCO-RD 7 ;
  • RD 2 is halogen, (Ci-C4)-haloalkyl, (Ci-C4)-haloalkoxy, nitro, (C1-C4)-alkyl, (Ci-C4)-alkoxy, (Ci-C4)-alkylsulfonyl, (Ci- C4)-alkoxycarbonyl or (Ci-C4)-alkylcarbonyl;
  • RD 3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl;
  • RD 4 is halogen, nitro, (C1-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-haloalkoxy, (C3-Ce)-cycloalkyl, phenyl, (Ci-C4)-alkoxy, cyano , (C1-C4)-alkylthio, (Ci-C4)-alkylsulfinyl, (Ci-C4)-alkylsulfonyl, (Ci-C4)alkoxycarbonyl or (Ci-C4)alkylcarbonyl;
  • RD 5 is hydrogen, (Ci-C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 5 -C 6 )-cycloalkenyl, phenyl or 3- to 6 -membered heterocyclyl containing VD heteroatoms from the group nitrogen, oxygen and sulfur, where the last seven radicals are substituted by VD substituents from the group halogen, (Ci-Ce) alkoxy, (Ci-Ce)haloalkoxy, (C1-C2) alkylsulfinyl, (C1-C2) alkylsulfonyl, (C3-Ce)cycloalkyl, (C1-C4) alkoxycarbonyl, (C1-C4) alkylcarbonyl and phenyl and in the case of cyclic radicals also (C1-C4)
  • RD 6 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkenyl or (C2-Ce)alkynyl, where the last three radicals are substituted by VD radicals from the group halogen, hydroxy, (C1-C4) alkyl, (C1-C4) alkoxy and (Ci- C4)alkylthio, or
  • RD 5 and RD 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;
  • RD 7 is hydrogen, (Ci-C4)alkylamino, di-(Ci-C4)alkylamino, (Ci-Ce)alkyl, (C3-Ce)cycloalkyl, where the last 2 radicals are substituted by VD substituents from the group halogen, (C1-C4)alkoxy, (Ci-Ce)haloalkoxy and (Ci-COalkylthio and in the case of cyclic radicals also (Ci-C alkyl and (Ci-COhaloalkyl); no is 0, 1 or 2; mo is 1 or 2;
  • VD is 0, 1, 2 or 3; preferred are compounds of the N-acylsulfonamide type, e.g. of the following formula (S4 a ), which are known, for example, from WO-A-97/45016 wherein
  • radicals are also substituted by (C1-C4)alkyl and (Ci-C4)haloalkyl;
  • VD is 0, 1, 2 or 3; and acylsulfamoylbenzoic acid amides, eg of the following formula (S4 b ), which are known eg from WO-A-99/16744, e.g. those in which
  • RD 8 and RD 9 independently of one another are hydrogen, (Ci-Cs)alkyl, (C3-Cs)cycloalkyl, (C3-Ce)alkenyl,
  • RD 4 represents halogen, (C1-C4) alkyl, (C1-C4) alkoxy, CF 3 mo 1 or 2; for example l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, l-[4-(N-4 ,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylurea.
  • 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.
  • 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-
  • AE is COORE 3 or COSRE 4
  • RE 3 , RE 4 are independently hydrogen, (C1-C4) alkyl, (Ci-C0) alkenyl, (C2-C4) alkynyl, cyanoalkyl, (Ci-C4) haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium, nE 1 is 0 or 1 nE 2 , nE 3 are independently 0, 1 or 2, preferably diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1).
  • RF 3 represents hydrogen, (Ci -Cs) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof, preferably compounds in which
  • X F CH, nF is an integer from 0 to 2 ,
  • RF 1 halogen, (C1-C4) alkyl, (Ci-C j haloalkyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, RF 2 hydrogen or (C1-C4) alkyl,
  • RF 3 denotes hydrogen, (Ci-Cs)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy, or a salt thereof.
  • Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones e.g. l,2-dihydro-4-hydroxy-l-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-l-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020.
  • YG, ZG independently of one another are O or S, nc is an integer from 0 to 4, RG 2 is (CI-Cie) alkyl, (Ci-Ce) alkenyl, (Cs-Cej cycloalkyl, aryl; benzyl, halobenzyl, RG 3 is hydrogen or (Ci-Ce) alkyl.
  • Si l Active substances of the oxyimino compound type (Si l), which are known as seed dressing agents, such as: B. "Oxabetrinil” ((Z)-l,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (Sl l-1), which is known as a seed dressing safener for millet against metolachlor damage, "Fluxofenim” (l-(4-chlorophenyl)-2,2,2-trifluoro-l-ethanone-O-(l,3-dioxolan-2-ylmethyl)-oxime) (Sl l-2), which is known as a seed dressing safener for millet against metolachlor damage, and "Cyometrinil” or “CGA-43089” ((Z)-cyanomethoxy-imino(phenyl)acetonitrile) (Sl l-3), which is known as a seed dressing safener for mill
  • Active ingredients from the class of isothiochromanones such as methyl [(3-oxo-lH-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361.
  • Active substances which, in addition to a herbicidal effect against harmful plants, also have a safener effect on cultivated plants such as rice, such as
  • RH 2 means hydrogen or halogen
  • RH 3 , RH 4 independently of one another are hydrogen, (Ci -Cie) alkyl, (C2-C16) alkenyl or (C2-Cie) alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (C1-C4) alkoxy, (C1-C4) haloalkoxy, (C1-C4) alkylthio,
  • RH 3 is (Ci-Ct -alkoxy, (C2-C4)alkenyloxy, (C2-Ce)alkynyloxy or (C2-C4)haloalkoxy and RH 4 is hydrogen or (Ci-C j-alkyl or
  • RH 3 and RH 4 together with the directly bonded N atom form a four- to eight-membered heterocyclic ring which, in addition to the N atom, can also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (C1-C4) alkyl, (Ci-C haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloal koxy and (Ci-C jalkylthio).
  • Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor, dichlormid and metcamifen.
  • Step 1 Synthesis of 3-(dihydromethyl)-6-(4,4-dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-2-(methylsulfanyl)aniline
  • Step 2 Synthesis of 2-amino-4-(difluoromethyl)-3-(methylsulfanyl)benzoic acid 3.00 g (10.5 mmol) of 3-(difluoromethyl)-6-(4,4-dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-2-(methylsulfanyl)aniline were mixed with 615 ml of 6M hydrochloric acid, then the reaction mixture was heated under reflux for 6 hours. For workup, the contents were largely concentrated. The suspension obtained as a residue was cooled in an ice bath and then filtered. The residue was washed twice with ice water and finally dried, whereby 1.68 g of the desired product were obtained.
  • Step 3 Synthesis of ethyl 2-amino-4-(difluoromethyl)-3-(methylsulfanyl)benzoate
  • Step 4 Synthesis of ethyl 2-chloro-4-(difluoromethyl)-3-(methylsulfanyl)benzoate
  • Step 6 Synthesis of 2-chloro-4-(difluoromethyl)-3-(methylsulfanyl)-N-(l,3,4-oxadiazol-2-yl)benzamide (Example No. 1-5)
  • 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 in a hammer mill.
  • a powder dissolved in water Easily dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of formula (I) and/or salts thereof, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurine as wetting agent. and dispersant and grinded in a pin 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 e.g. approx. 255 to over 277 C) and ground in a ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I) and/or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
  • a water-dispersible granulate is obtained by
  • a water-dispersible granulate is also obtained by
  • Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants are placed in sandy loam soil in wood fiber pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied to the surface of the covering soil as an aqueous suspension or emulsion with a water application rate of the equivalent of 600 to 800 l/ha and with the addition of 0.2% wetting agent. After treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants.
  • WP wettable powders
  • EC emulsion concentrates
  • Some of the compounds according to the invention show a high selectivity and are therefore suitable for use in the pre-emergence process for controlling undesirable plant growth in agricultural crops.
  • the data in the following tables show, by way of example, the herbicidal action of the compounds according to the invention in the pre-emergence process, with the herbicidal action being given in percent.
  • Table 3a Pre-emergence effect at 20g/ha against DIGSA in %
  • Table 3b Pre-emergence effect at 80g/ha against DIGSA in %
  • Table 5 Pre-emergence effect at 80g/ha against MATIN in %
  • Table 6a Pre-emergence effect at 20g/ha against SETVI in %
  • Table 7 Pre-emergence effect at 80g/ha against VERPE in %
  • Table 8a Pre-emergence effect at 20g/ha against VIOTR in %
  • Table 8b Pre-emergence effect at 80g/ha against VIOTR in %
  • Seeds of monocotyledonous or dicotyledonous weeds or cultivated plants are placed in wood fiber pots in sandy loam soil, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single-leaf stage.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed onto the green parts of the plant as an aqueous suspension or emulsion with a water application rate of the equivalent of 600 to 800 l/ha and with the addition of 0.2% wetting agent.
  • Table 10a Post-emergence effect at 5g/ha against AMARE in %
  • Table 10b Post-emergence effect at 20g/ha against AMARE in %
  • Table 13 Post-emergence effect at 80g/ha against LOLRI in %
  • Table 14a Post-emergence effect at 20g/ha against MATIN in %
  • Table 15 Post-emergence effect at 20g/ha against PHBPU in %
  • Table 16 Post-emergence effect at 20g/ha against SETVI in %
  • Table 17 Post-emergence effect at 20g/ha against VERPE in %

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Abstract

L'invention concerne des 4-difluorométhylbenzamides de formule (I) en tant qu'herbicides. Dans la formule (I), X, R et Ra représentent des groupes notamment alkyle, cycloalkyle, chlore et brome.
PCT/EP2024/055971 2023-03-17 2024-03-07 4-difluorométhyl benzamides à action herbicide Ceased WO2024194026A1 (fr)

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CN202480019442.2A CN120882703A (zh) 2023-03-17 2024-03-07 具有除草作用的4-二氟甲基苯甲酰胺
EP24709395.8A EP4680598A1 (fr) 2023-03-17 2024-03-07 4-difluorométhyl benzamides à action herbicide
MX2025010758A MX2025010758A (es) 2023-03-17 2025-09-11 Amidas de acido 4-difluorometilbenzoico de eficacia herbicida

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Citations (54)

* 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
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
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
EP0365484A1 (fr) 1988-10-20 1990-04-25 Ciba-Geigy Ag Sulfamoylphénylurées
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
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
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
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
WO2011035874A1 (fr) 2009-09-25 2011-03-31 Bayer Cropscience Ag N-(1,2,5-oxadiazol-3-yl) benzamides et leur utilisation comme herbicide
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
WO2012126932A1 (fr) 2011-03-22 2012-09-27 Bayer Cropscience Ag Amides d'acides n-(1,3,4-oxadiazol-2-yl)arylcarboxyliques et utilisation desdits amides d'acides n-(1,3,4-oxadiazol-2-yl)arylcarboxyliques comme herbicides
WO2016146561A1 (fr) 2015-03-17 2016-09-22 Bayer Cropscience Aktiengelsellschaft Sels d'amides d'acide arylcarboxylique n-(1,3,4-oxadiazol-2-yl) et leur utilisation comme herbicides
WO2018202535A1 (fr) 2017-05-04 2018-11-08 Bayer Cropscience Aktiengesellschaft 4-difluorométhylbenzoylamides à effet 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
WO2022189495A1 (fr) * 2021-03-12 2022-09-15 Bayer Aktiengesellschaft Amides d'acide n-(1,3,4-oxadiazole-2-yl)phényl-carboxylique chiraux et leur utilisation en tant qu'herbicides

Patent Citations (55)

* 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
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
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
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
EP0365484A1 (fr) 1988-10-20 1990-04-25 Ciba-Geigy Ag Sulfamoylphénylurées
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
WO2005016001A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Agents phytoprotecteurs a base de derives d'acide carboxylique aromatiques-aliphatiques
WO2005015994A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Utilisation d'aromates hydroxy comme phytoprotecteurs
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
WO2011035874A1 (fr) 2009-09-25 2011-03-31 Bayer Cropscience Ag N-(1,2,5-oxadiazol-3-yl) benzamides et leur utilisation comme herbicide
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
WO2012126932A1 (fr) 2011-03-22 2012-09-27 Bayer Cropscience Ag Amides d'acides n-(1,3,4-oxadiazol-2-yl)arylcarboxyliques et utilisation desdits amides d'acides n-(1,3,4-oxadiazol-2-yl)arylcarboxyliques comme herbicides
WO2016146561A1 (fr) 2015-03-17 2016-09-22 Bayer Cropscience Aktiengelsellschaft Sels d'amides d'acide arylcarboxylique n-(1,3,4-oxadiazol-2-yl) et leur utilisation comme herbicides
WO2018202535A1 (fr) 2017-05-04 2018-11-08 Bayer Cropscience Aktiengesellschaft 4-difluorométhylbenzoylamides à effet 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
WO2022189495A1 (fr) * 2021-03-12 2022-09-15 Bayer Aktiengesellschaft Amides d'acide n-(1,3,4-oxadiazole-2-yl)phényl-carboxylique chiraux et leur utilisation en tant qu'herbicides

Non-Patent Citations (21)

* Cited by examiner, † Cited by third party
Title
"Gene Transfer to Plants, Springer Lab Manual", 1995, SPRINGER VERLAG
"Microwaves in Organic and Medicinal Chemistry", 2005, VERLAG WILEY
"Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich", CHEMFILES, vol. 4, no. 1
"The Pesticide Manual", 2006, THE BRITISH CROP PROTECTION COUNCIL AND THE ROYAL SOC. OF CHEMISTRY
B. SAMBROOK ET AL.: "Molecular Cloning, A Laboratory Manual", 1989, COLD SPRING HARBOR LABORATORY PRESS
BARRY A. BUNIN: "The Combinatorial Index", 1998, VERLAG ACADEMIC PRESS
BRAUN ET AL., EMBO J., vol. 11, 1992, pages 3219 - 3227
D. TIEBES: "Combinatorial Chemistry - Synthesis, Analysis, Screening", 1999, VERLAG WILEY, pages: 1 - 34
G.C. KLINGMAN: "Weed Control as a Science", 1961, JOHN WILEY AND SONS, 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, BLACKWELL SCIENTIFIC PUBLICATIONS, pages: 101 - 103
J.E. BROWNING: "Agglomeration", 1967, CHEMICAL AND ENGINEERING, pages: 147
K. MARTENS: "Spray Drying'' Handbook", 1979, G. GOODWIN LTD.
MCCUTCHEON'S: "Encyclopedia of Surface Active Agents", 1964, CHEM. PUBL. CO. INC.
no. 133993-74-5
SCHÖNFELDT: "Grenzflächenaktive Äthylenoxidaddukte", 1976, WISS. VERLAGSGESELL.
SONNEWALD ET AL., PLANT J., vol. 1, 1991, pages 95 - 106
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, C. HANSER VERLAG, pages: 441 - 445
WOLTER ET AL., PROC. NATL. ACAD. SCI. USA, vol. 85, 1988, pages 846 - 850

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