EP1725103A1 - 4-(4-trifluoromethylpyrazolyle)-pyrimidines substituees, utilisees comme herbicides - Google Patents

4-(4-trifluoromethylpyrazolyle)-pyrimidines substituees, utilisees comme herbicides

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Publication number
EP1725103A1
EP1725103A1 EP05707643A EP05707643A EP1725103A1 EP 1725103 A1 EP1725103 A1 EP 1725103A1 EP 05707643 A EP05707643 A EP 05707643A EP 05707643 A EP05707643 A EP 05707643A EP 1725103 A1 EP1725103 A1 EP 1725103A1
Authority
EP
European Patent Office
Prior art keywords
halogen
alkyl
alkoxy
compounds
hydrogen
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.)
Withdrawn
Application number
EP05707643A
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German (de)
English (en)
Inventor
Michael Gerhard Hoffmann
Hendrik Helmke
Lothar Willms
Thomas Auler
Heinz Kehne
Martin Hills
Dieter Feucht
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 CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1725103A1 publication Critical patent/EP1725103A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the invention relates to the technical field of herbicides, in particular that of the herbicides from the group of heteroaryl pyrazoles for the selective control of weeds and weeds in crops of useful plants.
  • pyridines and pyrimidines which are substituted by azole radicals, such as pyrazolyl, imidazolyl and triazolyl, have herbicidal properties.
  • WO 99/28301 discloses pyridines and pyrimidines which carry an azole radical in the 2-position and an aromatic or heteroaromatic radical bonded via a carbon atom in the 4- or 6-position.
  • WO 98/40379 describes pyridines and pyrimidines which carry an azole radical in the 2-position and an aromatic or heteroaromatic radical bonded via an oxygen, nitrogen or sulfur atom in the 4- or 6-position.
  • the azole residue in the 2-position can be substituted by various residues.
  • the object of the present invention is therefore to provide herbicidally active compounds having improved herbicidal properties compared to the compounds disclosed in the prior art.
  • Y means a residue from the group Y1 to Y9:
  • R 1 and R 2 are independently hydrogen, halogen, cyano, isocyano, OH, COOR 9 , COR 9 , CH 2 OH, CH 2 SH, CH 2 NH 2> NO 2 , CSNH 2 , CONH 2 , (C r C 4 ) alkyl, halo (CC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl.
  • R 1 and R 2 together mean CH2-CH2-CH2, CH 2 -CH 2 -CH2-CH 2 or OCH 2 -
  • R 3 and R 4 independently of one another are hydrogen, halogen, cyano, (C 1 -C 4 ) -alkyl, halogen (C r C 4 ) -alkyl, (dC 4 ) -alkoxy or halogen- (C- ⁇ -C 4 ) alkoxy;
  • R 5 denotes halogen, cyano, (CC 4 ) alkyl, halogen (CC 4 ) alkyl, (CC 4 ) alkoxy, halogen (CC) alkoxy, halogen (C 1 -C 4 ) alkylthio, (C 3 -C 5 ) cycloalkyl, halogen (C 3 -C 5 ) cycloalkyl, SF 5) S (O) n R 8 , (C 2 -C 4 ) alkenyl or (C 2 -C) - alkynyl;
  • R 6 denotes hydrogen, halogen, cyano, (C 1 -C 4 ) alkyl, halogen ⁇ rC ⁇ alkyl, (C 1 -C 4 ) alkoxy, halogen (CC 4 ) alkoxy or S (O) n R 8 ;
  • R 7 represents (dC 4 ) alkyl
  • R 8 represents hydrogen, (CC 4 ) alkyl or halo (CC 4 ) alkyl
  • R 9 represents hydrogen or (CrC 4 ) alkyl
  • n 0, 1 or 2.
  • alkyl, alkenyl and alkynyl radicals having more than two or three carbon atoms can be straight-chain or branched.
  • Alkyl radicals mean methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl.
  • alkenyl means ethenyl, 1-propenyl, 2-propenyl and the various butenyl isomers.
  • Alkynyl means ethynyl, 1-propynyl, 2-propynyl and the various butynyl isomers.
  • alkynyloxy stands for HC- ⁇ CCH 2 O, CH 3 C ⁇ CCH 2 O and
  • Cycloalkyl means cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Halogen means fluorine, chlorine, bromine or iodine.
  • Haloalkyl means alkyl which is partially or completely substituted by halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine, for example CF 3> CHF 2 , CH 2 F, CF3CF2, CH2FCHCI, CCI3, CHCI2, CH2CH2CI;
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to other halogen-substituted radicals.
  • the compounds of the formula (I) can be present as stereoisomers. For example, if a double bond is present, diastereomers can occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur.
  • Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, e.g. obtained by chromatographic separation processes. Likewise, stereoisomers can be produced selectively by using stereoselective reactions using optically active starting materials and / or auxiliary substances.
  • the invention also relates to all stereoisomers and their mixtures which are encompassed by the general formula (I) but are not specifically defined.
  • N-oxides can be prepared according to methods known to the person skilled in the art by reaction with oxidizing reagents such as peracids, hydrogen peroxide and sodium perborate. Such methods are, for example, in TL Gilchrist, Comprehensive Organic Synthesis, Volume 7, pages 748 to 750, SV Ley, Ed., Pergamon Press.
  • Compounds of the formula (I) can in principle form salts by addition with a) acids such as hydrogen chloride, hydrogen bromide, nitric acid, phosphoric acid, sulfuric acid, acetic acid, oxalic acid, or b) bases such as pyridine, ammonia, triethylamine, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide.
  • acids such as hydrogen chloride, hydrogen bromide, nitric acid, phosphoric acid, sulfuric acid, acetic acid, oxalic acid
  • bases such as pyridine, ammonia, triethylamine, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide.
  • preferred embodiments of the compounds according to the invention always include the N-oxides and salts.
  • R 1 and R 2 independently of one another are hydrogen, halogen, cyano, hydroxyl, formyl, vinyl, (C 1 -C 4 ) -alkyl, halogen (CC 4 ) -alkyl, or (CC 4 ) alkoxy; or
  • R 1 and R 2 together represent CH2CH 2 CH 2 ;
  • R 3 and R 4 are independently hydrogen, halogen, methyl or methoxy;
  • Y represents a radical Y1, Y2, Y3, Y6, Y7, Y8 or Y9, and the other substituents and indices each have the meanings mentioned above.
  • R 1 is hydrogen, halogen, hydroxy, cyano, trifluoromethyl, methoxy, methyl or ethyl;
  • R 2 is hydrogen, hydroxy, methyl, ethyl, methoxy or ethoxy, or
  • R 1 and R 2 together CH 2 -CH 2 -CH 2 ;
  • R 3 and R 4 independently of one another denote hydrogen or methyl, and the other substituents and indices each have the meanings given above.
  • Preferred compounds of the general formula (I) are those in which R 5 is halogen, cyano, halogen (C 1 -C 2 ) alkyl, halogen (C C2) alkoxy or halogen (C 1 -C 2 ) alkylthio, and the other substituents and indices each have the meanings given above.
  • Y represents Y1, Y2, Y7, Y8 or Y9, and the other substituents and indices each have the meanings mentioned above.
  • the compounds of formula (I) according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants.
  • Perennial weeds that are difficult to control and that sprout from rhizomes, rhizomes or other permanent organs are also well captured by the active ingredients. It is usually irrelevant whether the substances are applied by pre-sowing, pre-emergence or post-emergence.
  • Some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned in detail, which can be controlled by the compounds according to the invention without the name being intended to restrict them to certain species.
  • Harmful plants occurring in the rice under the specific culture conditions such as, for example, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus, are also excellently combated by the active compounds according to the invention. If the compounds according to the invention are applied to the surface of the earth before germination, either the weed seedlings emerge completely or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.
  • the compounds according to the invention show an excellent action against Amaranthus retroflexus, Avena sp., Echinochloa sp., Cyperus serotinus, Lolium multiflorum, Setaria viridis, Sagittaria pygmaea, Scirpus juncoides, Sinapis sp. and Stellaria media.
  • the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds
  • crop plants of economically important crops such as, for example, wheat, barley, rye, rice, corn, sugar beet, cotton and soybeans are only insignificantly or not at all damaged.
  • they have excellent tolerability in wheat, barley, corn, rice and soybeans.
  • the present compounds are very suitable for the selective control of undesired plant growth in agricultural crops or in ornamental crops.
  • the active compounds can also be used to control harmful plants in crops of known or still to be developed genetically modified plants.
  • the transgenic plants are generally distinguished by special 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 concern e.g. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • Transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known.
  • B. of cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.
  • the compounds of the formula (I) can preferably be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been rendered genetically resistant.
  • new plants which have modified properties in comparison to previously occurring plants are, for example, classic breeding methods and the generation of mutants.
  • new plants with modified properties can be produced using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624).
  • transgenic crop plants which are active against certain herbicides of the glufosinate type (cf., for example, EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A -5013659) are resistant to produce transgenic crop plants, for example cotton, with the ability of Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259).
  • transgenic crop plants with modified fatty acid composition (WO 91/13972).
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences.
  • plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences.
  • base exchanges partial sequences removed or natural or synthetic sequences added.
  • adapters or linkers can be attached to the fragments.
  • 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 appropriately constructed ribozyme which 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 only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
  • the synthesized protein When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a particular compartment, z. B. the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such 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: 95-106 (1991).
  • 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 monocot and dicot plants.
  • the active compounds according to the invention are used in transgenic crops, in addition to the effects on harmful plants which can be observed in other crops, effects often occur which are specific to the application in the respective transgenic culture, for example a modified or specially expanded one Weed spectrum that can be controlled, changed 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 crop plants.
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the substances according to the invention have excellent growth-regulating properties in crop plants. They intervene regulating the plant's own metabolism and can thus be used to influence plant constituents in a targeted manner and to facilitate harvesting, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for 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 storage.
  • the compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also relates to herbicidal compositions which comprise compounds of the formula (I).
  • the compounds of formula (I) can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified.
  • Possible formulation options are, for example: wettable powder (SP), water-soluble powder (WP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray , Elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • SP wettable powder
  • WP water-soluble powder
  • EC emulsifiable concentrates
  • EW emulsions
  • SC Suspension concentrates
  • SC dispersions based on oil or
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or an inert substance, but also ionic and / or nonionic surfactants (wetting agents, dispersing agents), for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzene sulfates 2,2'-Dinaphthylmethane-6,6 , -disulfonic acid sodium, ligninsulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltauric acid sodium.
  • the herbicidal active ingredients are, for example, finely ground in customary apparatuses such as hammer mills, fan mills and
  • Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more surfactants ionic and / or nonionic type (emulsifiers).
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more surfactants ionic and / or nonionic type (emulsifiers).
  • emulsifiers which can be used: calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid, alkyl aryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensate sations occur, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene such as polyoxyethylene -sorbitanfettklader.
  • calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid, alkyl aryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensate sations.
  • alkyl polyethers sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene such as
  • 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. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants, such as those e.g. already listed above for the other types of formulation.
  • Emulsions e.g. Oil-in-water emulsions (EW) can, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as those e.g. already listed above for the other types of formulation.
  • EW Oil-in-water emulsions
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on 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.
  • adhesives e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils
  • Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • spray drying fluidized bed granulation
  • plate granulation mixing with high-speed mixers and extrusion without solid inert material.
  • spray granules see, for example, the process in "Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration”, Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
  • the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active ingredient of the formula (I).
  • the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance 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 mostly 5 to 20% by weight of active ingredient, 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 in liquid or solid form and which granulating aids, fillers, etc. are used.
  • the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity.
  • combinations with other pesticidally active substances such as insecticides, acaricides, herbicides, Manufacture fungicides, as well as with safeners, fertilizers and / or growth regulators, for example in the form of a finished formulation or as a tank mix.
  • pesticidally active substances such as insecticides, acaricides, herbicides, Manufacture fungicides, as well as with safeners, fertilizers and / or growth regulators, for example in the form of a finished formulation or as a tank mix.
  • active ingredients such as those described, for example, in Weed Research 26, 441-445 (1986) or "The Pesticide Manual", 11th edition, The British Crop Protection Council and the, can be used as combination partners for the active ingredients according to the invention in mixture formulations or in the tank mix Royal Soc. of Chemistry, 1997 and the literature cited therein.
  • Known herbicides which can be combined with the compounds of the formula (I) are, for example, the following active substances (note: the compounds are either with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name , possibly together with a usual code number): acetochlor; acifluorfen; aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and methyl acetate; alachlor; alloxydim; ametryn; amidosulfuron; amitrol; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516 H, ie 5-fluoro-2-phen
  • the formulations present in the commercial form are diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, using water. Preparations in the form of dust, ground granules or granules as well as sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate of the compounds of the formula (I) varies with the external conditions, such as temperature, humidity, the type of herbicide used, and others. It can fluctuate within wide limits, e.g. between 0.001 and 1.0 kg / ha or more active substance, but is preferably between 0.005 and 750 g / ha.
  • Dusting agents A dusting agent is obtained by mixing 10 parts by weight of a compound of the general formula (I) and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • Dispersible powder A wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of a compound of the general formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as the wetting agent. and dispersant mixes and grinds in a pin mill. 3. Dispersion concentrate
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the general formula (I), 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. Mixes parts of paraffinic mineral oil (boiling range approx. 255 to above 277 ° C) and grinds to a fineness of less than 5 microns in a attritor.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the general formula (I), 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 adding 25 parts by weight of a compound of the general formula (I), 5 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, 2 oleoylmethyl tauric acid sodium, 1 polyvinyl alcohol,
  • Seeds of monocotyledonous and dicotyledonous weed plants are laid out in sandy loam in cardboard pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders or emulsion concentrates are then applied as an aqueous suspension or emulsion with a water application rate of the equivalent of 600 to 800 l / ha in different dosages to the surface of the covering earth.
  • the pots are placed in the greenhouse and kept under good growth conditions for the weeds.
  • the optical damage to the plants or the emergence damage is assessed after a test period of 3 to 4 weeks in comparison to untreated controls.
  • 1.13, 1.14, 1.25, 1.26, 1.39 and 1.46 show a 100% action against Amaranthus retroflexus, Lolium multiflorum, Setaria viridis and at a dosage of 1000 g and less than 1000 g of active substance per hectare Stellaria media.
  • the compounds according to the invention of Examples Nos. 7.13, 9.13 and 9.14 show a 100% activity against Amaranthus retroflexus, Setaria viridis and Stellaria media.
  • Seeds of monocotyledonous and dicotyledonous harmful plants are laid out in cardboard pots in sandy loam soil, covered with soil and grown in the greenhouse under good growth conditions. Two to three weeks after sowing, the test plants are treated in a three-leaf study.
  • the compounds according to the invention formulated as wettable powder or as emulsion concentrates are sprayed onto the surface of the green parts of the plant in different dosages at a rate of water equivalent to 600 to 800 l / ha. After 3 to 4 weeks of standing of the test plants in the greenhouse the effect of the compounds is rated under optimal growth conditions.
  • the compounds according to the invention from examples 1.46 and 9.25 show a 100% activity against Amaranthus retroflexus, Avena fatua, Sinapis arvensis and Stellaria media.

Abstract

L'invention concerne des 4-(4-trifluorométhylpyrazolyle)-pyrimidines de formule (I) et leur utilisation comme herbicides. Dans cette formule générale (I), R1, R2, R3 et R4 désignent différents restes et Y désigne un reste aromatique ou hétéroaromatique.
EP05707643A 2004-03-10 2005-02-26 4-(4-trifluoromethylpyrazolyle)-pyrimidines substituees, utilisees comme herbicides Withdrawn EP1725103A1 (fr)

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Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5527923B2 (ja) * 2007-03-28 2014-06-25 公益財団法人相模中央化学研究所 パーフルオロアルキル基を有する複素環化合物およびその製造方法
JP5300225B2 (ja) * 2007-08-03 2013-09-25 バイエル・クロップサイエンス・アーゲー 除草剤トリアゾリルピリジンケトン類
US8097712B2 (en) 2007-11-07 2012-01-17 Beelogics Inc. Compositions for conferring tolerance to viral disease in social insects, and the use thereof
EP2135865A1 (fr) * 2008-06-17 2009-12-23 Bayer CropScience AG Acides de vinaigre substitués 1-(diazinyle)pyrazole-4-yl, leur procédé de fabrication et d'utilisation en tant qu'herbicides et régulateurs de croissance de plantes
GB0912946D0 (en) * 2009-07-24 2009-09-02 Addex Pharmaceuticals Sa New compounds 5
US8962584B2 (en) 2009-10-14 2015-02-24 Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. Compositions for controlling Varroa mites in bees
SG183407A1 (en) 2010-03-08 2012-09-27 Monsanto Technology Llc Polynucleotide molecules for gene regulation in plants
WO2013040116A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040049A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions pour lutter contre les mauvaises herbes
EP2756086B1 (fr) 2011-09-13 2018-02-21 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
US10829828B2 (en) 2011-09-13 2020-11-10 Monsanto Technology Llc Methods and compositions for weed control
CN103957696B (zh) 2011-09-13 2019-01-18 孟山都技术公司 用于杂草控制的方法和组合物
CA2848576A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Methodes et compositions de controle des mauvaises herbes comprenant l'application topique de polynucleotides inhibant la 4-hydroxyphenyl-pyruvate-dioxygenase (hppd)
AU2012308818B2 (en) 2011-09-13 2018-06-21 Monsanto Technology Llc Methods and compositions for weed control
EP2755987B1 (fr) 2011-09-13 2018-06-06 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
US10760086B2 (en) 2011-09-13 2020-09-01 Monsanto Technology Llc Methods and compositions for weed control
US10806146B2 (en) 2011-09-13 2020-10-20 Monsanto Technology Llc Methods and compositions for weed control
CA2873828A1 (fr) 2012-05-24 2013-11-28 A.B. Seeds Ltd. Arn a double brin nue interferent en agissant sur les molecules cibles dans des graines de plantes
EA032406B1 (ru) 2013-01-01 2019-05-31 Эй.Би. СИДЗ ЛТД. СПОСОБЫ ВВЕДЕНИЯ дсРНК В СЕМЕНА РАСТЕНИЙ ДЛЯ МОДУЛЯЦИИ ЭКСПРЕССИИ ГЕНОВ
US10683505B2 (en) 2013-01-01 2020-06-16 Monsanto Technology Llc Methods of introducing dsRNA to plant seeds for modulating gene expression
CA2905104A1 (fr) 2013-03-13 2014-10-09 Monsanto Technology Llc Controle des ivraies par application topique d'une composition herbicidecomprenant de l'arn a double brin
WO2014164761A1 (fr) 2013-03-13 2014-10-09 Monsanto Technology Llc Procédés et compositions utilisables pour lutter contre les mauvaises herbes
US10568328B2 (en) 2013-03-15 2020-02-25 Monsanto Technology Llc Methods and compositions for weed control
US9850496B2 (en) 2013-07-19 2017-12-26 Monsanto Technology Llc Compositions and methods for controlling Leptinotarsa
CA2918387C (fr) 2013-07-19 2021-11-02 Monsanto Technology Llc Compositions et methodes de lutte contre leptinotarsa
MX2016005778A (es) 2013-11-04 2016-12-20 Monsanto Technology Llc Composiciones y metodos para controlar infestaciones de plagas y parasitos de los artropodos.
UA119253C2 (uk) 2013-12-10 2019-05-27 Біолоджикс, Інк. Спосіб боротьби із вірусом у кліща varroa та у бджіл
AU2015206585A1 (en) 2014-01-15 2016-07-21 Monsanto Technology Llc Methods and compositions for weed control using EPSPS polynucleotides
CN110506752B (zh) 2014-04-01 2022-02-18 孟山都技术公司 用于控制虫害的组合物和方法
CN106795515B (zh) 2014-06-23 2021-06-08 孟山都技术公司 用于经由rna干扰调控基因表达的组合物和方法
US11807857B2 (en) 2014-06-25 2023-11-07 Monsanto Technology Llc Methods and compositions for delivering nucleic acids to plant cells and regulating gene expression
AU2015296700B2 (en) 2014-07-29 2021-10-21 Monsanto Technology Llc Compositions and methods for controlling insect pests
UA124255C2 (uk) 2015-01-22 2021-08-18 Монсанто Текнолоджі Елелсі Інсектицидна композиція та спосіб боротьби з leptinotarsa
AU2016270870A1 (en) 2015-06-02 2018-01-04 Monsanto Technology Llc Compositions and methods for delivery of a polynucleotide into a plant
WO2016196782A1 (fr) 2015-06-03 2016-12-08 Monsanto Technology Llc Procédés et compositions pour l'introduction d'acides nucléiques dans des plantes
EP3927695A1 (fr) 2019-02-20 2021-12-29 Bayer Aktiengesellschaft 4-(4-trifluorométhyl-6-cycloropylpyrazolyl)pyrimidines à action herbicide

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6172005B1 (en) * 1997-03-11 2001-01-09 E. I. Du Pont De Nemours And Company Heteroaryl azole herbicides
JPH10251255A (ja) * 1997-03-14 1998-09-22 Nissan Chem Ind Ltd アジン誘導体
US6525001B1 (en) 1997-12-03 2003-02-25 Mid-American Commercialization Corporation Substituted pyrimidine and pyridine herbicides
DE10234875A1 (de) * 2002-07-25 2004-02-05 Bayer Cropscience Gmbh 4-Trifluormethylpyrazolyl substituierte Pyridine und Pyrimidine
DE10234876A1 (de) * 2002-07-25 2004-02-05 Bayer Cropscience Gmbh 4-Trifluormethylpyrazolyl substituierte Pyridine und Pyrimidine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005089551A1 *

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US20050209106A1 (en) 2005-09-22
AR048749A1 (es) 2006-05-24
CA2559097A1 (fr) 2005-09-29
JP2007527879A (ja) 2007-10-04
EA200601659A1 (ru) 2007-04-27
CN1929738A (zh) 2007-03-14
AU2005223983A1 (en) 2005-09-29
TW200533665A (en) 2005-10-16
KR20060132932A (ko) 2006-12-22
US7312180B2 (en) 2007-12-25
DE102004011705A1 (de) 2005-09-29
WO2005089551A1 (fr) 2005-09-29

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