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WO1995006039A1 - Nouveaux derives d'acide phenylglyoxylique, leurs procedes de preparation et leur utilisation comme herbicides et comme regulateurs de croissance vegetale - Google Patents

Nouveaux derives d'acide phenylglyoxylique, leurs procedes de preparation et leur utilisation comme herbicides et comme regulateurs de croissance vegetale Download PDF

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Publication number
WO1995006039A1
WO1995006039A1 PCT/EP1994/002629 EP9402629W WO9506039A1 WO 1995006039 A1 WO1995006039 A1 WO 1995006039A1 EP 9402629 W EP9402629 W EP 9402629W WO 9506039 A1 WO9506039 A1 WO 9506039A1
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Prior art keywords
formula
alkoxy
alkyl
group
halogen
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PCT/EP1994/002629
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German (de)
English (en)
Inventor
Rainer SCHÜTZE
Klaus Bauer
Hermann Bieringer
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Hoechst Schering Agrevo Gmbh
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Filing date
Publication date
Application filed by Hoechst Schering Agrevo Gmbh filed Critical Hoechst Schering Agrevo Gmbh
Priority to AU76527/94A priority Critical patent/AU7652794A/en
Publication of WO1995006039A1 publication Critical patent/WO1995006039A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/38—Sulfur atoms
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms

Definitions

  • New phenylglyoxylic acid derivatives processes for their preparation and their use as herbicides and plant growth regulators
  • the invention relates to the technical field of herbicides and plant growth regulators, in particular herbicides for the selective control of weeds and weeds in crops of useful plants.
  • the present invention relates to compounds of the formula (I)
  • R 1 H (C., - C 8 alkyl, which is unsubstituted or by one or more radicals from the group halogen, nitro, cyano, (C 1 -C 4 ) alkoxy, aryl and substituted aryl, or (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) alkynyl or aryl, where the aryl radical is unsubstituted or by one or more radicals from the group halogen, nitro, (C 1 -C 4 ) -Alkyl, (C., ⁇ ) - alkoxy and [(C 1 -C 4 ) -alkoxy] carbonyl, or a cation suitable for agriculture, for example a metal cation, in particular alkali or alkaline earth metal cation, or an unsubstituted or substituted ammonium ion,
  • R 2 and R 3 independently of one another (C r C 4 ) alkyl, (C r C 4 ) haloalkyl, (C r C 4 ) -
  • R 4 H halogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, (C r C 4 ) alkoxycarbonyl, nitro, cyano, or a group of the formula Q defined below,
  • R 5 , R 6 each independently of one another are H, (C r C 4 ) -alkyl which is unsubstituted or substituted by one or more radicals from the group halogen, (C 1 -C 4 ) -alkoxy or aryl, or (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) alkynyl or aryl which is unsubstituted or by one or more radicals from the group halogen, nitro, (C r C 4 ) alkyl, (C r C 4 ) - Alkoxy and (C r C 4 ) -haloalkoxy is substituted, or together with the N atom connecting them a heterocyclic radical with 3 to 7 ring atoms, which in addition to the N atom as a hetero ring atom has one or two further hetero ring atoms from the group N, O and S may be present in the possible oxidation states and may be unsubstituted or substitute
  • R 2 ' , R 3' , X 'and Y' are defined analogously to the meanings of the corresponding radicals R 2 , R 3 , X and Y in formula (I).
  • hydrocarbon-containing radicals such as. B. alkyl, alkoxy, haloalkyl and alkylthio radicals and the corresponding unsaturated and / or substituted radicals in the hydrocarbon part may each be straight-chain or branched.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl, etc., mean methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl;
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, such as 2-propenyl, 2- or 3-butenyl, 2-propynyl, 2- or 3-butynyl.
  • Halogen means fluorine, chlorine, bromine or iodine.
  • Haloalkyl means alkyl which is substituted by one or more atoms from the group halogen; Haloalkyl is, for example, CF 3 , CHF 2 , CH 2 CF 3 .
  • Aryl is, for example, phenyl, naphthyl, tetrahydronaphthyl, indanyl, fluorenyl and the like, preferably phenyl.
  • Substituted aryl or substituted phenyl preferably means aryl or phenyl, which is substituted by one or more, preferably 1 to 3, radicals from the group halogen, alkyl, haloalkyl, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkanoyl, carbamoyl, mono- and di-alkylaminocarbonyl , Mono- and dialkylamino, alkylsulfinyl or alkylsulfonyl is substituted, the alkyl-containing radicals having 1 to 4 carbon atoms, in particular 1 to 2 carbon atoms, being preferred; methyl, methoxy and chlorine are particularly preferred.
  • Heterocyclic radicals for the group NR 5 R 6 are, for example, saturated, unsaturated and heteroaromatic radicals of optionally substituted compounds from the group pyrrole, imidazole, pyrazole, triazole, oxazole, propanesultam, butanesulfame, pyrrolidone, pyrazolone and their partially or completely hydrogenated system such as piperidine , Piperazine or morpholine.
  • the invention also relates to all stereoisomers which are encompassed by formula (I) and mixtures thereof.
  • Such compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds which are not indicated separately in the general formula (I).
  • the possible stereoisomers defined by their specific spatial shape such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formulas (I) and can be obtained by conventional methods from mixtures of the stereoisomers or by stereoselective reactions in combination with the Use of stereochemically pure starting materials.
  • Preferred compounds of the formula (I) according to the invention are those in which R 1 is H, (Ci "C 5 ) alkyl which is unsubstituted or substituted by one or more radicals from the group halogen and (C r C 4 ) alkoxy, ( C 3 -C 6 ) alkenyl, (C 3 -C 6 ) alkynyl, an alkali metal cation, an alkaline earth metal cation or an ammonium ion (NH 4 ⁇ ), preferably H, (C- Cs.-alkyl which is unsubstituted or singly or repeatedly by Halogen or (C., ⁇ ) - alkoxy is substituted,
  • R 2 and R 3 independently of one another (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C - C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy or halogen, preferably (-C-C 4 ) alkoxy or (C 1 -C 4 ) alkyl, in particular OCH 3 ,
  • R 4 H halogen, (CC 4 ) -alkyl, (C r C 4 ) -alkoxy, (CC 4 -alkoxycarbonyl, nitro, cyano or a group of the formula Q, preferably H, Cl, CH 3 , OCH 3 , CO 2 CH 3 , NO 2 or a group of the formula Q, X 0 or S, preferably O,
  • Y is CH or N, preferably CH
  • R 2 ' , R 3' , X 'and Y' are defined analogously to R 2 , R 3 , X and Y in formula (I).
  • R 2 and R 3 independently of one another (C-
  • R 4 H halogen, (C r C 4 ) alkyl, (C r C 4 ) alkoxy, Nitro, cyano or a group Q, preferably H, Cl, CH 3 , OCH 3 , CO 2 CH 3 , NO 2 or a group Q,
  • X is an oxygen atom
  • Y is a group of the formula CH
  • W is an oxygen atom
  • R 2 ' , R 3' , X 'and Y' are defined as R 2 , R 3 , X and Y in formula (I).
  • R 2 and R 3 each OCH 3 ,
  • R 4 H halogen, CH 3 , OCH 3 , CO 2 CH 3 , nitro or a group Q,
  • the invention further relates to processes for the preparation of the compounds of the formula (I) according to the invention, characterized in that
  • Nuc is a leaving group, such as. B. Cl or CH 3 -SO 2 -, reacted, wherein in the formulas (II) to (VI) above R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X and Y as in formula (I) are defined.
  • reaction with chloroformate (variant c) is carried out, for example, in dipolar aprotic solvents, preferably N, N-dimethylformamide, at room temperature under the action of a base.
  • dipolar aprotic solvents preferably N, N-dimethylformamide
  • 2-mercaptophenylglyoxylic acid takes place, for. B. in polar protic solvents, preferably water under the action of alkali metal hydroxides.
  • polar protic solvents preferably water under the action of alkali metal hydroxides.
  • the reaction of the 2-hydroxyphenylglyoxylic acid is generally carried out in dipolar aprotic solvents, preferably N, N-dimethylformamide.
  • the optionally substituted 2-mercaptophenylglyoxylic acid is obtained by methods known from the literature by reacting (subst.) Thiophenol with oxalyl chloride and cyclizing the resulting oxalic acid thiohaloester chloride in an intramolecular Friedel-Crafts acylation to give the (subst.) Benzothiophendione, which is then hydrolysed and acidified which provides (subst.) 2-mercaptophenylglyoxylic acid.
  • the (subst.) 2-hydroxyphenylglyoxylic acid can also be obtained by methods known from the literature (Chem. Reports 17, 973 (1886)) by basic hydrolysis of isatin, the resulting 2-aminophenylglyoxylic acid and the diazonium salt being subjected to a phenol boil.
  • ⁇ available methylthioethers can be prepared by oxidation with oxone (potassium peroxodisulfate).
  • 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 does not matter whether the substances are pre-seeded, pre-emergence or Post-emergence procedures are applied.
  • the spectrum of activity extends to species such as: B. Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida on the annual side as well as Convolvulus, Cirsium, Rumex and Artemisia for the perennial weeds.
  • 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 have excellent herbicidal activity against mono- and dicotyledon weeds, crop plants of economically important crops, such as, for. B. wheat, barley, rye, rice, corn, sugar beet, cotton and soy are only slightly or not at all damaged. For these reasons, the present compounds are very suitable for the selective control of undesired plant growth in agricultural crops.
  • the compounds of the formula (I) according to the invention have excellent growth-regulating properties in crop plants. They intervene regulatively in the plant's own metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, e.g. B. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesired 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 of formula (I) according to the invention can be used in the customary formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules.
  • the invention therefore also relates to herbicidal and plant growth-regulating compositions which comprise compounds of the formula (I) or their salts.
  • the compounds of formula (I) can be formulated in different ways, depending on which biological and / or chemical-physical parameters are specified.
  • formulation options come in, for example Question: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC) , Oil or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), pickling agents, 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.
  • WP wettable powder
  • SP water-soluble powder
  • EC emulsifiable concentrates
  • 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), e.g. B.
  • the herbicidal active ingredients are finely ground, for example in conventional apparatus such as hammer mills, fan mills and air jet mills, and mixed at the same time or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents
  • surfactants of ionic and / or nonionic type emulsifiers
  • alkylarylsulfonic acid calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. B. sorbitan fatty acid esters or polyoxethylene sorbitan esters such. B. polyoxyethylene sorbitan fatty acid ester.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. B. 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 z. B. already listed above for the other types of formulation.
  • Emulsions e.g. B. oil-in-water emulsions (EW) can be, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as z. B. are already listed above for the other types of formulation.
  • 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. As polyvinyl alcohol, sodium polyacrylic acid 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. As polyvinyl alcohol, sodium polyacrylic acid or mineral oils
  • Water-dispersible granules are generally produced using the customary processes, such as spray drying, fluidized bed granulation, plate 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 active compound of the formula (I) or salts thereof.
  • the active ingredient concentration is z. B. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components.
  • the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight.
  • Dust-like formulations contain 1 to 30, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions 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.
  • active substances can be used, for example, as described in e.g. B. from Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 9th edition, The British Crop Protection Council, 1990/91, Bracknell, England, and literature cited therein.
  • herbicides known from the literature which can be combined with the compounds of formula (I), z.
  • the following active substances are to be named (note: the compounds are identified either with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name, if appropriate together with a customary 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; amitrole; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; aziprotryn; barban; BAS 516 H, ie 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; benazolin; benfluorflu
  • the formulations present in the commercial form are optionally diluted in the customary manner, for. B. with wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Preparations in the form of dust, ground or scatter granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the compounds of the invention can, for example, directly on the harmful plants or harmful plants and crop plants at the same time in the post-emergence process or on the area on which the plants grow, for. B. on arable soil with plant seeds or accumulated plants or on acreages, such as. B. a rice cultivation area, applied in the pre- or post-emergence process.
  • the required application rate of the compounds of formula (I) varies. It can fluctuate within wide limits, e.g. B. between 0.001 and 10.0 kg / ha or more of active substance, but is preferably between 0.005 and 5 kg / ha.
  • the mixture is heated under reflux for 2 hours, allowed to cool to room temperature, the solution is brought to pH 1 with concentrated hydrochloric acid and extracted twice with 50 ml of ethyl acetate.
  • the combined organic phases are dried over MgSO 4 , the drying agent is filtered off and the solvent is distilled off under reduced pressure.
  • Ph phenyl
  • a dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as an inert substance and comminuting in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I),
  • quartz containing kaolin as an inert substance
  • potassium lignosulfonate 1 part by weight sodium oleoylmethyl taurine as wetting and dispersing agent and ground in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) 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.
  • Parts of paraffinic mineral oil (boiling range e.g. approx. 255 to above 277 ° C) and mixed in one Grinding ball mill ground to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the 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:
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants were placed in sandy loam in plastic pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders or emulsion concentrates were 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 were placed in the greenhouse and kept under good growth conditions for the weeds. After the test plants had emerged, the optical damage to the plants or the emergence damage was assessed after a test period of 3 to 4 weeks in comparison to untreated controls. As the test results show, the compounds according to the invention have good herbicidal pre-emergence activity against a broad spectrum of grasses and weeds.
  • the compounds of Examples 1, 2, 3, 4, 11, 12, 14, 56, 59, 60, 61, 62, 66, 67, 68, 75, 77 and 78 have very good herbicidal activity against harmful plants such as Sinapis alba, Chrysanthemum segetum, Avena sativa, Stellaria media, Echinochloa crus-galli, Lolium multiflorum, Setaria spp., Abutilon theophrasti, Amaranthus retroflexus and Panicum miliaceum in the pre-emergence process with an application rate of 0.3 kg and less active substance per hectare.
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were placed in plastic pots in sandy loam soil, covered with soil and grown in the greenhouse under good growth conditions.
  • the test plants were treated at the three-leaf stage three weeks after sowing.
  • the compounds according to the invention formulated as wettable powder or as emulsion concentrates, were sprayed onto the green parts of the plant in various dosages with a water application rate of the equivalent of 600 to 800 l / ha, and after about 3 to 4 weeks of standing of the test plants in the greenhouse under optimal growth conditions, the action of the preparations visually rated in comparison to untreated controls.
  • the agents according to the invention also have good herbicidal activity against a broad spectrum of economically important grasses and weeds, even after emergence.
  • the compounds of Examples 1, 2, 3, 4, 11, 12, 14, 56, 59, 60, 61, 62, 66, 67, 68, 75, 77 and 78 have very good herbicidal activity against harmful plants such as Sinapis alba, Stellaria media, Echinochloa crus-galli, Lolium multiflorum, Chrysanthemum segetum, Setaria spp., Abutilon theophrasti, Amaranthus retroflexus and Panicum miliaceum, Avena sativa in the post-emergence process with an application rate of 0.3 kg and less active substance per hectare.

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

Abstract

Composés de la formule (I), dans laquelle R1 désigne H, alkyle (C¿1?-C8), éventuellement substitué par halogène, nitro, cyano, alcoxy (C1-C4), aryle et aryle substitué, ou alkényle (C3-C6), alkinyle (C3-C6) ou aryle (subst.) ou un cation approprié à l'utilisation en agriculture, R?2 et R3¿ désignent indépendamment l'un de l'autre alkyle (C¿1?-C4), haloalkyle (C1-C4), alcoxy (C1-C4) ou haloalcoxy (C1-C4), halogène ou mono- ou Di(alkyle C1-C4) -amino, R?4¿ désigne H, halogène, alkyle (C¿1?-C4), alcoxy (C1-C4), alcoxycarbonyle (C1-C4), nitro, cyano ou un groupe Q, X = O ou S, Y = CH ou N, W = O, S, N-OR?5, N-NR5R6, R5, R6¿ désignent H, alkyle (C¿1?-C4) (subst.), alkényle (C3-C6), alkinyle (C3-C6) ou aryle (subst.) ou conjointement avec l'atome de N, un reste hétérocyclique (subst.) ayant entre 3 et 7 atomes cycliques et Q désigne un groupe de la formule (a) dans laquelle R?2', R3'¿, X' et Y' ont une notation analogue à celle de R2, R3, X et Y dans la formule (I). Ces composés s'utilisent comme herbicides et comme régulateurs de croissance végétale. Leur préparation peut s'effectuer selon les procédés décrits dans la revendication 5.
PCT/EP1994/002629 1993-08-24 1994-08-08 Nouveaux derives d'acide phenylglyoxylique, leurs procedes de preparation et leur utilisation comme herbicides et comme regulateurs de croissance vegetale WO1995006039A1 (fr)

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AU76527/94A AU7652794A (en) 1993-08-24 1994-08-08 Novel phenyl glyoxylic acid derivatives, processes for producing them and their use as herbicides and plant growth regulators

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DEP4328414.0 1993-08-24
DE19934328414 DE4328414A1 (de) 1993-08-24 1993-08-24 Neue Phenylglyoxylsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren

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WO (1) WO1995006039A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5747528A (en) * 1996-02-21 1998-05-05 Warner-Lambert Company Chroman derivatives as anti-oxidants
JP2008019241A (ja) * 2007-03-01 2008-01-31 Mitsubishi Tanabe Pharma Corp オキシム誘導体及びその製法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0468684A2 (fr) * 1990-07-27 1992-01-29 Zeneca Limited Dérivés de l'acide propénique, procédé pour leur préparation et leur utilisation comme fongicides
EP0472113A1 (fr) * 1990-08-22 1992-02-26 Kumiai Chemical Industry Co., Ltd. Dérivés de pyrimidine et compositions herbicides les contenant
GB2249092A (en) * 1990-10-25 1992-04-29 Ici Plc Oxime ether fungicides
EP0549344A1 (fr) * 1991-12-27 1993-06-30 Sumitomo Chemical Company, Limited Dérivés de triazine comme herbicides
EP0555488A1 (fr) * 1991-07-31 1993-08-18 Kumiai Chemical Industry Co., Ltd. Derive de pyrimidine ou de triasine et herbicide contenant ledit derive

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0468684A2 (fr) * 1990-07-27 1992-01-29 Zeneca Limited Dérivés de l'acide propénique, procédé pour leur préparation et leur utilisation comme fongicides
EP0472113A1 (fr) * 1990-08-22 1992-02-26 Kumiai Chemical Industry Co., Ltd. Dérivés de pyrimidine et compositions herbicides les contenant
GB2249092A (en) * 1990-10-25 1992-04-29 Ici Plc Oxime ether fungicides
EP0555488A1 (fr) * 1991-07-31 1993-08-18 Kumiai Chemical Industry Co., Ltd. Derive de pyrimidine ou de triasine et herbicide contenant ledit derive
EP0549344A1 (fr) * 1991-12-27 1993-06-30 Sumitomo Chemical Company, Limited Dérivés de triazine comme herbicides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5747528A (en) * 1996-02-21 1998-05-05 Warner-Lambert Company Chroman derivatives as anti-oxidants
JP2008019241A (ja) * 2007-03-01 2008-01-31 Mitsubishi Tanabe Pharma Corp オキシム誘導体及びその製法

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DE4328414A1 (de) 1995-05-04
AU7652794A (en) 1995-03-21

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