DE3101889A1 - Novel phenoxycarboxamides, their preparation, and their use as herbicides - Google Patents

Novel phenoxycarboxamides, their preparation, and their use as herbicides

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Publication number
DE3101889A1
DE3101889A1 DE19813101889 DE3101889A DE3101889A1 DE 3101889 A1 DE3101889 A1 DE 3101889A1 DE 19813101889 DE19813101889 DE 19813101889 DE 3101889 A DE3101889 A DE 3101889A DE 3101889 A1 DE3101889 A1 DE 3101889A1
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formula
alkyl
weight
compounds
phenoxycarboxamides
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DE19813101889
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German (de)
Inventor
Klaus Dr. 6054 Rodgau Bauer
Hermann Dipl.-Agraring. Dr. 6239 Vockenhausen Bieringer
Hubert Dr. 6074 Rödermark Schönowsky
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Hoechst AG
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Hoechst AG
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Priority to DE19813101889 priority Critical patent/DE3101889A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • 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
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • 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
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • C07D251/44—One nitrogen atom with halogen atoms attached to the two other ring carbon 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
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

Phenoxycarboxamides of the formula <IMAGE> in which R denotes halogen, alkyl or halophenoxy, R1 and R2 denote H or alkyl, Het denotes a substituted pyridine, thiazole, thiophene, thiadiazole or triazine radical, and n denotes 1, 2 or 3, are potent herbicides.

Description

Neue Phencxycarbonsäureamide, Verfahren zu ihrerNew Phencxycarboxamides, Process for their

Herstellung und ihre Verwendung als Herbizide Gegenstand der vorliegenden Erfindung sind neue Phenoxycarbonsäureamide der Formel I, worin R = Halogen, (C1-C4)-Alkyl, Mono- oder Dihalogenphenoxy, R1 und R2 = Wasserstoff oder (C1-C4)-Alkyl, Het = ein gegebenenfalls ein- oder zweifach durch Halogen, Niti:o, (C1-C4)-Alkyl, (C1-Cq)-Alkoxy und/ oder (C1-C2)-alkoxycarbonyl substituierter Pyridin-, Thiazol-, Thiophen-, Thiadiazol- oder Triazinrest sowie n = 1, 2 oder 3 bedeuten.Production and their use as herbicides The present invention relates to new phenoxycarboxamides of the formula I, where R = halogen, (C1-C4) -alkyl, mono- or dihalophenoxy, R1 and R2 = hydrogen or (C1-C4) -alkyl, Het = one optionally one or two times by halogen, Niti: o, (C1- C4) -alkyl, (C1-Cq) -alkoxy and / or (C1-C2) -alkoxycarbonyl-substituted pyridine, thiazole, thiophene, thiadiazole or triazine radical and n = 1, 2 or 3.

Man erhält die Verbindungen der Formel I, indem rhan Phenoxycarbonsäurehalogenide der Formel II mit heterocyclischen Aminen der Formel III umsetzt.The compounds of the formula I are obtained by adding phenoxycarboxylic acid halides of the formula II with heterocyclic amines of the formula III implements.

Die Umsetzung wird vorteilhaft in einem organischen Lösungsmittel wie z.B. Butanon, Dimethoxiethan, Toluol u.a. vorgenommen. Zur Bindung des freiwerdenden Halogenwasserstoffs arbeitet man in Gegenwart einer Base, vorzugsweise einer tertiären organischen Base wie Triethylamin ode einer alkalischen Verbindung wie MgO oder K2CO3.The reaction is advantageously carried out in an organic solvent such as butanone, dimethoxyethane, toluene and others. To bind what is released Hydrogen halide is carried out in the presence of a base, preferably a tertiary one organic base such as triethylamine or an alkaline compound such as MgO or K2CO3.

Nach beendeter Reaktion wird das gebildete halooenwasserstoffsaure Salz durch Filtration oder durch Behandeln mit Wasser abgetrennt, und - gegebenenfalls nach abschließender Entfernung des organischen Lösungsmittels - das gebildete Amid isoliert.After the reaction has ended, the hydrofluoric acid formed is The salt is separated off by filtration or by treatment with water, and - if appropriate after final removal of the organic solvent - the amide formed isolated.

Die so erhaltenen Verbindungen I können nach üblichen Verfahren z. B. Umkristallisieren aus goeigneten Lösungsmitteln gereinigt werden.The compounds I obtained in this way can, by conventional methods, for. B. recrystallization from suitable solvents.

Die erfindungsgemäßen Verbindungen eignen sich zur Bekämpfung von unerwünschtem Pflanzenwuchs im Vor-und Nachauflauf. Sie zeichnen sich besonders durch eine gute herbizide Wirkung gegen breitblättrige Unkräuter z.B. Cruciferenarten, Galium (Klettenlabkraut) und wärmeliebende Arten wie Amaranthus, Sida, Abutylon und Ipomoea aus. Gegen Gräser sind sie unwirksam, so daß sie zur selektive Unkrautbekämpfung in Gramineenkulturen, wie Weizen, Reis, Gerste, Roggen und Sorghum eingesetzt werden können.The compounds according to the invention are suitable for combating unwanted vegetation in pre- and post-emergence. You stand out particularly due to a good herbicidal effect against broad-leaved weeds e.g. crucifera species, Galium (burdock weed) and heat-loving species such as Amaranthus, Sida, Abutylon and Ipomoea from. They are ineffective against grasses, so they can be used for selective weed control in graminaceous crops such as wheat, rice, barley, rye and sorghum can.

Die Verträglichkeit der erfindungsgemäßen Verbindungen I in den bereits erwähnten grasartigen Kulturen ist außerordentlich gut, so werden noch bei Konzentrationen von 2,4 kg/ha keine oder nur geringfügige Schäden an der Kulturpflanze festgestellt.The compatibility of the compounds I according to the invention in the already mentioned grassy crops is extraordinarily good, so are still at concentrations of 2.4 kg / ha, no or only minor damage to the crop was found.

Gegenstand der vorliegenden Erfindung sind daher auch herbizide Mittel, die gekennzeichnet sind durch einen Gehalt an einem Wirkstoff der Formel I im allgemeinen zu 2-95 Gew.-. Sie können als Spritzpulver, emulgierbare Konzentrate, versprühbare Lösungen, Stäubemittel oder Granulate in den üblichen Zubereitungen angewendet werden.The present invention therefore also relates to herbicidal agents which are characterized by a content of an active ingredient of the formula I in general to 2-95 wt. They can be used as wettable powders, emulsifiable concentrates, sprayable Solutions, dusts or granules can be used in the usual preparations.

Spritzpulver sind in Wasser gleichmäRig dispergierbare Präparate, die neben dem Wirkstoff auger einem Verdünnungs- oder Inertstoff noch Netzmittel, z.B. polyoxethylierte Alkylphenole, polyoxethylierte Fettalkohole, A1Kyl- oder Alkylphenyl-sulfonate und Dispergiermittel, z.B. ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalinsulfonssaures Natrium oder auch oleylmethyltaurinsaurcs Natrium enthalten.Wettable powders are preparations that are uniformly dispersible in water, which, in addition to the active ingredient as well as a diluent or inert substance, also include wetting agents, e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, A1Kyl- or alkylphenyl-sulfonates and dispersants such as sodium lignin sulfonic acid, 2,2'-dinaphthylmethane-6,6'-disulfonic acid Sodium, sodium dibutylnaphthalenesulfonic acid or oleylmethyltaurine acid Contain sodium.

Emulgierbare Konzentrate werden durch Auflösen des airkstoffes in einem organischen Lösungsmittel, z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen unter Zusatz von einem oder mehreren Emulgatoren hergestellt. Als Emulgatoren können beispielsweise verwandt werden: Alkylarylsulfonsaure Calziumsalze wie Ca-dodecylbenzolsulfonat, oder nichtionische Emulgatoren wie Fettsäurepolyglkolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Et.hylenoxid-Kondensationsprodukte, Fettalkohol-Propylenoxid-Ethylenoxid- Kondensationsprodukte, Alkylpolyether, Sorbitanfettsäureester, Polyoxethylen-sorbitan-fettsäureester oder Polyoxethylen-sorbitester.Emulsifiable concentrates are made by dissolving the airkstoffes in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or several emulsifiers. As emulsifiers, for example, can be used be: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate, or non-ionic Emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, Propylene oxide-ethylene oxide condensation products, fatty alcohol-propylene oxide-ethylene oxide- Condensation products, Alkyl polyethers, sorbitan fatty acid esters, polyoxethylene sorbitan fatty acid esters or Polyoxethylene sorbitol ester.

Stäubemittel erhält man durch Vermahlen des Wirkstoffes mit fein verteilten, festen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit, Pyrophillit oder Diatomeenerde.Dust is obtained by grinding the active ingredient with finely divided, solid substances, e.g. talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.

Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol,polyacrylsaurem Natrium oder auch Mineralölen auf die Oberfläche von Trägerstoffen, wie Sand, Kaolinite, oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranalien üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - hergestellt werden.Granules can either be sprayed onto adsorptive, Granulated inert material can be produced or by applying active ingredient concentrates by means of adhesives, e.g. polyvinyl alcohol, polyacrylic acid sodium or mineral oils on the surface of carrier materials such as sand, kaolinite, or granulated Inert material. Suitable active ingredients can also be used in the production of fertilizer granules the usual way - if desired in a mixture with fertilizers - are produced.

Bei herbiziden Mitteln können die Konzentrationen der Wirkstoffe in den handelsüblichen bormunierungen verschieden sein.In the case of herbicidal agents, the concentrations of the active ingredients can be in be different from the customary boron fittings.

In Spritzpulvern variiert die Wirkstoffkonzentration z.B.In wettable powders, the active ingredient concentration varies e.g.

zwischen etwa 10 e/t und 80 , der Rest besteht aus den oben angegebenen Formulierungszusätzen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration gleichfalls etwa 10 bis 8G betragen. Staubförmige Formulierungen enthalten meistens 5 - 20 % an Wirkstoff, versprühbare Lösungen etwa 2 - 20 56. Bei Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden.between about 10 e / t and 80, the remainder consists of the above Formulation additives. In the case of emulsifiable concentrates, the active ingredient concentration can also be about 10 to 8G. Dust-like formulations mostly contain 5 - 20% active ingredient, sprayable solutions around 2 - 20 56. With granules it depends the active ingredient content depends in part on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.

Zur Anwendung werden die handelsüblichen Konzentrate gegebenenfalls in üblicher Weise verdurnt, z.B. bei Spritzpulvern und emulgierbaren Konzentraten mittels Wasser.The commercially available concentrates are optionally used for use Diluted in the usual way, e.g. with wettable powders and emulsifiable concentrates by means of water.

Staubförmige und granulierte Zubereitungen sowie versprühbare Lösungen werden vor der Anwendung nicht mehr mit weiteren inerten Stoffen verdünnt. Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, u.a. variiert die erforderliche Aufwendmenge. Sie beträgt im allgemeinen etwa 0,3 - 4 kg/ha, vorzugsweise etwa 0,5 bis 3 kg/ha Wirkstoff. Der erfindungsgemaNe Wirkstoff kann mit anderen Herbiziden, Insektiziden, Akariziden und Fungiziden kombiniert werden.Dust-like and granulated preparations as well as sprayable solutions are no longer diluted with other inert substances before use. With the External conditions such as temperature, humidity, etc., the required varies Expenditure amount. It is generally about 0.3-4 kg / ha, preferably about 0.5 up to 3 kg / ha active ingredient. The active ingredient according to the invention can be combined with other herbicides, Insecticides, acaricides and fungicides are combined.

Eine andere Anwendungsform der vorliegenden Wirkstoffe besteht in ihrer Mischung mit Düngemitteln, wodurch düngende und zugleich herbizide Mittel erhalten werden.Another application form of the present active ingredients consists in Mixing them with fertilizers, creating fertilizing and at the same time herbicidal agents can be obtained.

Herstellungsbeispiele Allgemeine Verschrift zur Herstellung der Phenoxycarbonsäureamide der allgemeinen Formel I Zu 0,1 mol Säurechlorid, gelöst in 50 ml Toluol, werden 0,1 mol Triethylamin zugesetzt. Bei 25 - 40 OC werden dann 0,1 mol eines heterocyclischen Amins zugetropft.Preparation examples General instructions for the preparation of the phenoxycarboxamides of the general formula I To 0.1 mol of acid chloride dissolved in 50 ml of toluene 0.1 mol of triethylamine added. At 25-40 ° C., 0.1 mol of a heterocyclic Amine was added dropwise.

Man läßt 1 h nachreagieren und setzt dann Wasser zu.The reaction is allowed to continue for 1 hour and then water is added.

Die Toluolphase wird abgetrennt, mit Wasser gewaschen und über Natriumsulfat getrocknet. Nach Abdestillieren des Toluols wird das Amid isoliert und durch Umkristallisieren gereinigt.The toluene phase is separated off, washed with water and over sodium sulfate dried. After the toluene has been distilled off, the amide is isolated and recrystallized cleaned.

In folgender Tabelle sind die so hergestellten Verbindungen zusammengefaßt. Bei- (R) R, H, Het Fp. COC~7 n C1 ~ 1 2,4-CL H H 117 - 120 E-I H 2 2,4-Cl H H C)441C1 83 - 86 Br 3 -2,4-Cl H H > 100 - 103 NO Cl 4 2,4-Cl H H N0 zuCl 134 - 136 Bei- (R) R1 R2 Het Fp. Lot 7 spiel Nr. NO2 Br 5 2,4-C1 H H N0 W r 146 - 147 6 2,4-C1 IT H jffi1Br 153 - 255 BrBr 7 2,4-C1 C'da H 166 - 168 Br 8 r 2-CH3, CH3 H Br 122 - 124 4-Cl NO2 Br g I 2-CH3, CH3 H N02 X bs 163 - 164 4-Cl NO2 Cl 10 2-CH, , CH3 H No2 C1 151 - 153 4-Cl Br Br 11 2-CH3, CH3 H o 190 - 192 4-Cl 12 2,4-C1 CH5 H 13 2,4-C1 CHa H NO2 Cl 14 2,4-C1 -CH5 H No2 C1 140 - 142 Bei- (R)n R1 R2 Het Fp. gC 7 spiel Nr. 15 4-O--C1 CH H 107 - 108 107 - 108 16 4-o-(O)-cl CH H NO2 2 Cl 149 - 151 4ri 17 2,4-C1 H CH3 WsN\C(CH.) N 122122 - 1D N-N ~ ~ N~N 18 2-CH32 CH3 CH3 t s\>C(CH3)3 123 - 126 4-C1 s C2H500C CM5 91 - 93 ig 2,4-C1 H H I I rC OCz Hs 21 2,4-C1 CH3 )I 230 - 232 22 2-CII,, CH, H 11 244 - 245 4-C1 C1 N 24 2,4-C1 CH3 M 25 2-CH5, CH5 H n 136 - 138 4-C1 Bei- (R R, R2 Met afp. E0C7 spiel I Nr. CH3 N 26 2-CH3, CH3 H SSA 168 - 170 4-C1 5 27 2,4-C1 H H 28 2,4-C1 CH3 H The compounds produced in this way are summarized in the following table. At- (R) R, H, Het m.p. COC ~ 7 n C1 ~ 1 2,4-CL HH 117-120 EI H 2 2,4-Cl HHC) 441C1 83-86 Br 3 -2,4-Cl HH> 100-103 NO Cl 4 2,4-Cl HH N0 to Cl 134-136 Bei- (R) R1 R2 Het Fp. Lot 7 game No. NO2 Br 5 2,4-C1 HH N0 W r 146 - 147 6 2,4-C1 IT H jffi1Br 153-255 BrBr 7 2,4-C1 C'da H 166-168 Br 8 r 2-CH3, CH3 H Br 122-124 4-Cl NO2 Br g I 2-CH3, CH3 H NO2 X bs 163-164 4-Cl NO2 Cl 10 2-CH,, CH3 H No2 C1 151-153 4-Cl Br Br 11 2-CH3, CH3 HO 190-192 4-Cl 12 2,4-C1 CH5 H 13 2,4-C1 CHa H NO2 Cl 14 2,4-C1 -CH5 H No2 C1 140 - 142 At- (R) n R1 R2 Het m.p. gC 7 game No. 15 4-O-C1 CH H 107-108 107-108 16 4-o- (O) -cl CH H NO2 2 Cl 149-151 4ri 17 2,4-C1 H CH3 WsN \ C (CH.) N 122122-1D NN ~ ~ N ~ N 18 2-CH32 CH3 CH3 ts \> C (CH3) 3 123 - 126 4-C1 s C2H500C CM5 91-93 ig 2,4-C1 HH II rC OCz Hs 21 2,4-C1 CH3) I 230-232 22 2-CII ,, CH, H 11 244-245 4-C1 C1 N 24 2,4-C1 CH3 M 25 2-CH5, CH5 H n 136-138 4-C1 At- (RR, R2 Met afp. E0C7 game I. No. CH3 N 26 2-CH3, CH3 H SSA 168-170 4-C1 5 27 2,4-C1 HH 28 2,4-C1 CH3 H

Formullerungsbelspiele Beispiel A In Wasser leicht dispergierbare, benetzbare Pulver werden erhalten, indem man die nachstehend aufgeführten Bestandteile mischt und in einer Stiftmühle mahlt: 50 Gew.-% Wirkstoff der Formel I 5 Gew.-% Dispergiermittel (Na-Salz eines Kondensationsproduktes aus Naphthalinsulfonsa.cure und Formaldehyd) 3 Gew.-% Dialkylarylsulfonsaures Natrium 3 Gcw.-% Fcttsuremethyltaurid-Natrium 4 Gew. -% Polyvinylalkohol 10 Gew.-% Calciumligninsulfonat 25 Gew.-% feindisperse Kieselsäure Beispiel B In Wasser leicht emulgierbare Emulsionskonzentrate werden erhalten durch Mischen der nachstehend aufgeführten Bestandteile: 10 Gew.-% Wirkstoff der Formel I 60 Gew.-t Mineralcl (aromatisch) 18 Gew.-% Emulgatorgemisch aus Ca-dodecylbenzolsulfonat und Nonylphenolpolyglykolether 5 Gew.-% Oxethyliertes Polypropylenglykol 7 Gew.-% Verdunstungshemmer (hcchsiedender aromatischer Ester) Beispiel C Staubformulierungen werden erhalten, indem man die nachstehend aufgeführten Bestandteile mischt und in einer Stiftmühle mahlt: 60 Gew.-% Wirkstoff der Formel I 35 Gew.-% Talkum-Pulver 5 Gew.-% Haftmittel Beispiel D In Wasser leicht dispergierbare Dispersicnskonzentrate werden erhalten, indem man die nachstehend aufgeführten Bestandteile mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt: 25 Gew.-% Wirkstoff der Formel I 15 Gew.-% Emulgatorgemisch aus Ca-dodecylbenzolsulfonat und Nonylphenolpolyglykolether 10 Gew.-% Tributylphenolpolyglykolether 50 Gew.-% Weißöl (paraffinisches Mineralöl) Beispiel E Granulate werden erhalten, indem man die nachstehend aufgeführten Bestandteile mischt und in die Granulatform überführt: 25 Gew.-% Wirkstoff der Formel I 35 Gew.-% Kreide (feinpulvrig) 15 Gew.-t Attapulgit-Pulver 5 Gew.-% Polyvinyalkohol 8 Gew.-% Natriumligninsulfonat 4 Gew.-% Dialkylarylsulfonsaures-Natrium 6 Gew.-% Dispergiermittel (Na-Salz eine Kondensationsproduktes aus Formaldehyd und aromatischen Sulfonsäuren) 2 Gew.-% Na-carboxymethylcellulose Biologische Beispiele Verschiedene wirtschaftlich bedeutende Unkräuter und landwirtschaftliche Kulturpflanzen wurden in Töpfen mit sandiger Lehmerde ausgesät und unter Gewächshausbedingungen bis zum Dreiblattstadium der Testpflanzen angezogen. Anschließend wurden die erfindungsgemäßen Verbindungen in verschiedenen Konzentrationen auf das Pflanzenmaterial appliziert, wobei das Volumen der Spritzbrühe pro Topf einer Menge von umgerechnet 600 2 ha entsprach.Die Pflanzen wurden dann unter Gewächshausbedingungen aufgestellt und ca. 3 Wochen später auf Schadwirkung visuell bonitiert.Formulation examples Example A Easily dispersible in water, Wettable powders are obtained by adding the ingredients listed below mixes and grinds in a pin mill: 50 wt .-% active ingredient of the formula I 5 wt .-% Dispersant (Na salt of a condensation product from Naphthalenesulfonsa.cure and formaldehyde) 3% by weight of dialkylarylsulphonic acid, sodium 3% by weight of methyltauride, sodium 4% by weight polyvinyl alcohol 10% by weight calcium lignosulfonate 25% by weight finely dispersed Silicic Acid Example B Emulsion concentrates which can be easily emulsified in water are used obtained by mixing the ingredients listed below: 10% by weight of active ingredient of formula I 60 wt. t mineral oil (aromatic) 18 wt.% emulsifier mixture of calcium dodecylbenzenesulfonate and nonylphenol polyglycol ether 5% by weight Oxethylated polypropylene glycol 7% by weight Evaporation Inhibitors (High-Boiling Aromatic Esters) Example C Dust Formulations are obtained by mixing the ingredients listed below and grinds in a pin mill: 60% by weight of active ingredient of the formula I 35 % By weight talc powder 5% by weight adhesive. Example D Easily dispersible in water Dispersion concentrates are obtained by adding the ingredients listed below mixed and ground in a friction ball mill to a fineness of less than 5 microns: 25% by weight of active ingredient of the formula I 15% by weight of emulsifier mixture of calcium dodecylbenzenesulfonate and nonylphenol polyglycol ether 10% by weight tributylphenol polyglycol ether 50% by weight White oil (paraffinic mineral oil) Example E Granules are obtained by mixes the ingredients listed below and converts them into granulate form: 25% by weight of active ingredient of the formula I 35% by weight of chalk (finely powdered) 15% by weight of attapulgite powder 5% by weight of polyvinyl alcohol, 8% by weight of sodium lignin sulfonate, 4% by weight of sodium dialkylarylsulfonic acid 6 wt .-% dispersant (Na salt a condensation product of formaldehyde and aromatic sulfonic acids) 2% by weight Na-carboxymethyl cellulose Biological Examples Various economically significant weeds and agricultural Cultivated plants were sown in pots with sandy loam and under greenhouse conditions grown to the three-leaf stage of the test plants. Then the invention Compounds applied in different concentrations to the plant material, the volume of the spray liquid per pot being the equivalent of 600 2 ha The plants were then placed under greenhouse conditions and visually rated for harmful effects approx. 3 weeks later.

Die durch die Versuchspräparate verursachte Schädigung bzw. Abtötung wurde in Prozenten im Vergleich zur unbehandelten Kontrolle (Schädigung = O ,4) ausgedrückt.The damage or death caused by the test preparations was in percent compared to the untreated control (damage = 0.4) expressed.

Die Ergebnisse dieser Versuche (Tabelle l) zeigen, daß die erfindungsgemaßen Verbindungen bei 2,4 bzw. 0,6 ka AS/ha dikotyle Unkräuter völlig vernichten, monokotyle Kulturpflanzen wie Weizen, Gerste, Reis, Mais und Sorghum hingegen weitgehend schonen. Die erfindungsgemäßen Verbindungen eignen sich deshalb hervorragend dazu, unerwünschten Pflanzenwuchs in Getreide-, Reis- und Maiskulturen zu bekämpfen.The results of these tests (Table 1) show that the invention Completely destroy compounds at 2.4 or 0.6 ka AS / ha dicotyledon weeds, monocotyledonous On the other hand, conserve crops such as wheat, barley, rice, maize and sorghum to a large extent. The compounds according to the invention are therefore outstandingly suitable for treating undesired Combat plant growth in grain, rice and maize crops.

Tabelle 1: Herbizide wirkung gegen verschiedene Unkräuter und Selektivität im Nachauflaufverfahren (Schadwirkung in %) Bei- Dosis SIA AtR IPP TA HV OS ZM SV spiel (kg Nr. AS/ha) 1 2,4 100 100 100 20 20 10 10 30 0,6 100 100 100 10 10 0 0 0 2 2,4 100 lC0 100 0 0 0 -0,6 100 90 100 0 0 0 - 0 3 2,4 100 90 100 0 20 30 0 0 0,6 100 70 100 0 10 0 0 0 20 2,4 100 100 100 10 10 0 0 10 0,6 100 95 100 0 0 0 0 0 Abkürzunen: SIA = Ackersenf OS = Reis AMR = Amaranth ZM = Mais IPP = Prunkwinde SV = Sorghum TA = Weizen AS = Aktivsubstanz HV = GersteTable 1: Herbicidal activity against various weeds and selectivity in the post-emergence method (harmful effect in%) at dose SIA AtR IPP TA HV OS ZM SV play (kg No.AS / ha) 1 2.4 100 100 100 20 20 10 10 30 0.6 100 100 100 10 10 0 0 0 2 2.4 100 lC0 100 0 0 0 -0.6 100 90 100 0 0 0 - 0 3 2.4 100 90 100 0 20 30 0 0 0.6 100 70 100 0 10 0 0 0 20 2.4 100 100 100 10 10 0 0 10 0.6 100 95 100 0 0 0 0 0 Abbreviations: SIA = field mustard OS = rice AMR = amaranth ZM = maize IPP = morning glory SV = sorghum TA = wheat AS = active ingredient HV = barley

Claims (5)

ANSPRUCHE 1. phenoxycarbonsäureamide der Formel I worin R = Halogen, (C1-C4)-Alkyl, Mono- oder Dihalogenphenoxy, R1 und R2 = Wasserstoff oder (C1-C4)-Alkyl, Het = ein gegebenenfalls ein- oder zweifach durch Halogen, Nitro, (C1-C4)-Alkyl, tC1-C4)-Alkoxy und/ oder (C1-C2) -Aloxycarbonyl substituierter Pyridin-, Thiazol-, Thiophen-, Thiadiazol- oder Triazinrest sowie n = 1, 2 oder 3 bedeuten.CLAIMS 1. phenoxycarboxamides of the formula I. where R = halogen, (C1-C4) -alkyl, mono- or dihalophenoxy, R1 and R2 = hydrogen or (C1-C4) -alkyl, Het = one optionally one or two times by halogen, nitro, (C1-C4) -Alkyl, tC1-C4) -alkoxy and / or (C1-C2) -aloxycarbonyl-substituted pyridine, thiazole, thiophene, thiadiazole or triazine radical and n = 1, 2 or 3. 2. Verfahren zur Herstellung von Verbindungen der Formel I, dadurch gekennzeichnet, daß man Phenoxycarbonsäurehalogenide der Formel II worin Hal Chlor oder Brom bedeutet, mit heterocyclischen Aminen der Formel III in Gegenwart von Basen umsetzt.2. Process for the preparation of compounds of the formula I, characterized in that phenoxycarboxylic acid halides of the formula II wherein Hal is chlorine or bromine, with heterocyclic amines of the formula III converts in the presence of bases. 3. Herbizide Mittel, gekennzeichnet durch einen wirksamen Gehalt an Verbindungen der Formel I.3. Herbicidal agents, characterized by an effective content of Compounds of formula I. 4. Verwendung von Verbindungen der Formel I zur Bekämpfung von unerwünschtem Pflanzenwuchs.4. Use of compounds of the formula I for combating undesirable substances Vegetation. 5. Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, dadurch gekennzeichnet, daß man auf die Pflanzen bzw. die von ihnen befallene Fläche eine wirksame Menge einer Verbindung der Formel I aufbringt.5. A method for controlling unwanted vegetation, thereby characterized in that one is on the plants or the area infested by them effective amount of a compound of formula I applies.
DE19813101889 1981-01-22 1981-01-22 Novel phenoxycarboxamides, their preparation, and their use as herbicides Withdrawn DE3101889A1 (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63249461A (en) * 1987-04-02 1988-10-17 Mitsuba Electric Mfg Co Ltd Magnetically coupled structure
EP0423523A2 (en) * 1989-10-07 1991-04-24 BASF Aktiengesellschaft Carboxylic acid amides, process for their preparation and their use as herbicides
US5071865A (en) * 1989-06-14 1991-12-10 Bayer Aktiengesellschaft Pesticidal 2-acylamino-4-halogeno-5-nitrothiazoles
US5139564A (en) * 1985-11-19 1992-08-18 Park Sang W Herbicidal aryloxyacetic acid derivatives
JP2011515369A (en) * 2008-03-19 2011-05-19 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト Fungicide hydroxymoyl-tetrazole derivative
EP2411007A2 (en) * 2009-03-27 2012-02-01 The UAB Research Foundation Modulating ires-mediated translation
CN104163792A (en) * 2013-05-20 2014-11-26 湖南化工研究院 N-picolinamide compound, preparation method and application thereof
WO2022008923A1 (en) 2020-07-10 2022-01-13 MOA Technology Limited Herbicidal heterocyclic derivatives

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5139564A (en) * 1985-11-19 1992-08-18 Park Sang W Herbicidal aryloxyacetic acid derivatives
JPS63249461A (en) * 1987-04-02 1988-10-17 Mitsuba Electric Mfg Co Ltd Magnetically coupled structure
JPH0477548B2 (en) * 1987-04-02 1992-12-08 Mitsuba Electric Mfg Co
US5071865A (en) * 1989-06-14 1991-12-10 Bayer Aktiengesellschaft Pesticidal 2-acylamino-4-halogeno-5-nitrothiazoles
US5201934A (en) * 1989-10-07 1993-04-13 Basf Aktiengesellschaft Carboxamides and their use as herbicides
EP0423523A3 (en) * 1989-10-07 1992-02-19 Basf Aktiengesellschaft Carboxylic acid amides, process for their preparation and their use as herbicides
EP0423523A2 (en) * 1989-10-07 1991-04-24 BASF Aktiengesellschaft Carboxylic acid amides, process for their preparation and their use as herbicides
JP2011515369A (en) * 2008-03-19 2011-05-19 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト Fungicide hydroxymoyl-tetrazole derivative
EP2411007A2 (en) * 2009-03-27 2012-02-01 The UAB Research Foundation Modulating ires-mediated translation
EP2411007A4 (en) * 2009-03-27 2012-12-05 Uab Research Foundation Modulating ires-mediated translation
CN104163792A (en) * 2013-05-20 2014-11-26 湖南化工研究院 N-picolinamide compound, preparation method and application thereof
WO2014187298A1 (en) * 2013-05-20 2014-11-27 湖南化工研究院有限公司 N-pyridine amide compound, preparation method therefor, and application thereof
WO2022008923A1 (en) 2020-07-10 2022-01-13 MOA Technology Limited Herbicidal heterocyclic derivatives

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