EP0000051A1 - N-acylmethyl-chloroacetanilides, process for their preparation and their use as herbicides. - Google Patents

N-acylmethyl-chloroacetanilides, process for their preparation and their use as herbicides. Download PDF

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Publication number
EP0000051A1
EP0000051A1 EP78100091A EP78100091A EP0000051A1 EP 0000051 A1 EP0000051 A1 EP 0000051A1 EP 78100091 A EP78100091 A EP 78100091A EP 78100091 A EP78100091 A EP 78100091A EP 0000051 A1 EP0000051 A1 EP 0000051A1
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Prior art keywords
chloroacetanilides
acylmethyl
alkyl
halogen
preparation
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EP78100091A
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German (de)
French (fr)
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EP0000051B1 (en
Inventor
Erik Ing.-(Grad) Regel
Ludwig Dr. Eue
Robert Rudolf Dr. Schmidt
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Bayer AG
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Bayer AG
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    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides

Definitions

  • the present invention relates to new N-acylmethyl-chloroacetanilides, a process for their preparation and their use as herbicides.
  • chloroacetanilides such as, for example, 2-ethyl-6-methyl-N- (1'-methyl-2'-methoxy-ethyl) -chloroacetanilide
  • these compounds are not equally effective against all grasses and their selectivity is not always entirely satisfactory.
  • N-acylmethyl-chloroacetanilides according to the invention are superior to the previously known chloroacetanilides, such as 2-ethyl-6-methyl-N- (1'-methyl-2'-methoxy-ethyl) -chloroacetanilide, because in addition to the Grasses Setaria, Lolium and Echinochloa especially Sinapis is better recorded. They also show better selectivity in important crops.
  • the active compounds according to the invention thus represent an essential enrichment of the herbicidal compositions.
  • R preferably represents straight-chain or branched alkyl having 1 to 6, in particular 1 to 4, carbon atoms, halogen, in particular fluorine, chlorine and bromine, haloalkyl having up to 3 carbon atoms and up to 5 identical or different halogen atoms, with halogens in particular fluorine and chlorine, for example trifluoromethyl; further preferably for alkylthio and alkylsulfonyl having 1 to 4 carbon atoms in the alkyl part and for aminosulfonyl, cyano and nitro.
  • R 1 and R 2 are identical or different and are preferably hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, halogen, in particular fluorine, chlorine and bromine, haloalkyl with up to 3 carbon atoms and up to 5 identical or different halogen atoms, the halogens being in particular fluorine and chlorine and preferably phenyl which is monosubstituted or polysubstituted, the substituents mentioned for R being preferred R 3 preferably represents straight-chain or branched alkyl having 1 to 6, in particular 1 to 4, carbon atoms and optionally optionally mono- or polysubstituted phenyl, the substituents which are preferably the radicals already mentioned for R and phenyl and phenoxy, which are likewise represented by R may be substituted.
  • N-acylmethyl-anilines of the formula (II) are known (see, inter alia, Bischler, Chem. Ber. 25, 2865 (1892) and Crowther, Mann, Purdie, Chem. Soc. 1943, 63) or can be prepared by known methods . They are obtained, for example, by anilines with a-haloketones in the presence of an organic solvent, e.g. Ethanol, implemented (see also the manufacturing examples).
  • Inert organic solvents are preferably suitable as diluents for the reaction according to the invention.
  • These preferably include ketones, such as diethyl ketone, in particular acetone and methyl ethyl ketone; Nitriles, such as propionitrile, especially acetonitrile; Ethers such as tetrahydrofuran or dioxane; aliphatic and aromatic hydrocarbons, such as petroleum ether, benzene, toluene or xylene; halogenated hydrocarbons such as methylene chloride, carbon tetrachloride, chloroform or chlorobenzene; and esters, such as ethyl acetate.
  • ketones such as diethyl ketone, in particular acetone and methyl ethyl ketone
  • Nitriles such as propionitrile, especially acetonitrile
  • Ethers such as tetrahydrofuran or dioxane
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, between 0 and 120 ° C, preferably between 20 and 100 ° C.
  • the active compounds according to the invention influence the planter growth and can therefore be used as defoliants, desiccants, haulm killers, germ inhibitors and, in particular, as weed killers. Weeds in the broadest sense are all plants that grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops can e.g. Forestry, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annual crops.
  • the active compounds according to the invention can preferably be used for selective weed control and in particular weed control in various crops.
  • the active compounds according to the invention it is already - in contrast to those used as grass herbicides known chloroacetanilides - possible, in addition to dicotyledons, e.g. Galinsoga and Sinapis, also the difficult to control weed Avena fatua or Alopecurus at the same time as other harmful grasses, e.g. Digitaria, Echinochloa, Panicum and / or Setaria in crops such as sugar beet, soybeans, beans, cotton, rape , Peanuts, vegetables, corn and rice.
  • the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules. These are manufactured in a known manner, e.g. B. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene, benzene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B.
  • Liquefied gaseous scattering agents or carriers mean liquids which are gaseous at normal temperature and under normal pressure, e.g. B.
  • aerosol propellants such as dichlorodifluoromethane or trichlorofluoromethane; as solid carriers: natural rock flour, such as kaolins, clays, talc, chalk, Quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates; as an emulsifier; nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as a dispersant: e.g. B. lignin sulfite and methyl cellulose.
  • natural rock flour such as kaolins, clays, talc, chalk, Quartz, attapulgite, montmorillonite or diatomaceous earth and
  • the active compounds according to the invention as such or in their formulations for strengthening and supplementing their spectrum of action, can be combined with other herbicidal active compounds, depending on the intended use, finished formulation or tank mixture being possible.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90% by weight.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They are used in the usual way, e.g. by spraying, spraying, dusting, scattering and pouring.
  • the active compounds according to the invention can be applied both after and in particular before the plants emerge. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can fluctuate in larger areas. It essentially depends on the type of effect you want. In general, the application rates are between 0.1 and 10 kg of active ingredient per ha, preferably between 0.2 and 5 kg / ha.
  • the active compounds according to the invention can also be mixed with other herbicides, e.g. with metamitron for sugar beet, with metribuzin for soybeans, with atrazine for corn and with diuron or fluomethuron for cotton.
  • herbicides e.g. with metamitron for sugar beet, with metribuzin for soybeans, with atrazine for corn and with diuron or fluomethuron for cotton.
  • Solvent 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Abstract

1. N-Alcylmethyl-chloroacetanilides of the formula see diagramm : EP0000051,P12,F1 in which R represents alkyl, halogen, halogenoalkyl, alkylthio, alkylsulphonyl, aminosulphonyl, cyano or nitro, R**1 and R**2 are identical or different and represent hydrogen, alkyl, halogen, halogenoalkyl or optionally substituted phenyl, R**3 represents alkyl or optionally substituted phenyl and n represents integers from 0 to 5.

Description

Die vorliegende Erfindung betrifft neue N-Acylmethyl-chloracetanilide, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide.The present invention relates to new N-acylmethyl-chloroacetanilides, a process for their preparation and their use as herbicides.

Es ist bereits bekannt geworden, daß Chloracetanilide, wie beispielsweise 2-Aethyl-6-methyl-N-(1'-methyl-2'-methoxy-äthyl)-chloracetanilid, als Herbizide, insbesondere zur Bekämpfung von grasartigen Unkräutern, verwendet werden können (vergleiche DT- 'OS 2 328 340). Diese Verbindungen sind jedoch nicht gegen alle Gräser gleich gut wirksam und in ihrer Selektivität nicht immer ganz befriedigend.It has already become known that chloroacetanilides, such as, for example, 2-ethyl-6-methyl-N- (1'-methyl-2'-methoxy-ethyl) -chloroacetanilide, can be used as herbicides, in particular for controlling grass-like weeds (see DT- 'OS 2 328 340). However, these compounds are not equally effective against all grasses and their selectivity is not always entirely satisfactory.

Es wurden neue N-Acylmethyl-chloracetanilide der Formel

Figure imgb0001
in welcher

  • R für Alkyl, Halogen, Halogenalkyl, Alkylthio, Alkylsulfonyl, Aminosulfonyl, Cyano oder Nitro steht,
  • R1 und R2 gleich oder verschieden sind und für Wasserstoff, Alkyl, Halogen, Halogenalkyl oder gegebenenfalls substituiertes Phenyl stehen,
  • R3 für Alkyl oder gegebenenfalls substituiertes Phenyl steht und
  • n für ganze Zahlen von 0 bis 5 steht,

aufgefunden.There were new N-acylmethyl-chloroacetanilides of the formula
Figure imgb0001
 in which
  • R represents alkyl, halogen, haloalkyl, alkylthio, alkylsulfonyl, aminosulfonyl, cyano or nitro,
  • R 1 and R 2 are the same or different and represent hydrogen, alkyl, halogen, haloalkyl or optionally substituted phenyl,
  • R 3 represents alkyl or optionally substituted phenyl and
  • n stands for integers from 0 to 5,

found.

Diese neuen N-Acylmethyl-chloracetanilide weisen starke herbizide, insbesondere auch selektiv-herbizide Eigenschaften auf.These new N-acylmethyl chloroacetanilides have strong herbicidal, in particular also selective herbicidal properties.

Weiterhin wurde gefunden, daß man die N-Acylmethyl-chloracetanilide der Formel (I) erhält, wenn man N-Acylmethylaniline der Formel

Figure imgb0002
in welcher

  • R,R' ,R2,R3 und n die oben angegebene Bedeutung haben.

mit Chloracetylchlorid in Gegenwart eines Verdünnungsmittels umsetzt.Furthermore, it was found that the N-acylmethyl-chloroacetanilides of the formula (I) are obtained when N-acylmethylanilines of the formula
Figure imgb0002
 in which
  • R, R ', R 2 , R 3 and n have the meaning given above.

reacted with chloroacetyl chloride in the presence of a diluent.

Ueberraschenderweise sind die erfindungsgemäßen N-Acylmethyl-chloracetanilide den vorbekannten Chloracetaniliden, wie beispielsweise 2-Aethyl-6-methyl-N-(1'-methyl-2'-methoxy-äthyl)-chloracetanilid, in der herbiziden Wirkung überlegen, da neben den Gräsern Setaria, Lolium und Echinochloa vor allem auch Sinapis besser erfaßt wird. Außerdem zeigen sie eine bessere Selektivität in wichtigen Kulturpflanzen. Die erfindungsgemäßen Wirkstoffe stellen somit eine wesentliche Bereicherung der herbiziden Mittel dar.Surprisingly, the N-acylmethyl-chloroacetanilides according to the invention are superior to the previously known chloroacetanilides, such as 2-ethyl-6-methyl-N- (1'-methyl-2'-methoxy-ethyl) -chloroacetanilide, because in addition to the Grasses Setaria, Lolium and Echinochloa especially Sinapis is better recorded. They also show better selectivity in important crops. The active compounds according to the invention thus represent an essential enrichment of the herbicidal compositions.

Verwendet man 2,6-Dimethyl-N-benzoylmethyl-anilin und Chloracetylchlorid als Ausgangsstoffe, so kann der Reaktionsablauf durch das folgende Formelschema wiedergegeben werden:

Figure imgb0003
If 2,6-dimethyl-N-benzoylmethyl-aniline and chloroacetyl chloride are used as starting materials, the course of the reaction can be represented by the following formula:
Figure imgb0003

Die als Ausgangsstoffe zu verwendenden N-Acylmethyl-aniline sind durch die Formel (II) allgemein definiert. In dieser Formel steht R vorzugsweise für geradkettiges oder verzweigtes Alkyl mit 1 bis 6, insbesondere 1 bis 4 Kohlenstoffatomen, Halogen, insbesondere Fluor, Chlor und Brom, Halogenalkyl mit bis zu 3 Kohlenstoff- und bis zu 5 gleichen oder verschiedenen Halogenatomen, wobei als Halogene insbesondere Fluor und Chlor stehen, beispielhaft sei Trifluormethyl genannt; ferner vorzugsweise für Alkylthio und Alkylsulfonyl mit 1 bis 4 Kohlenstoffatomen im Alkylteil sowie für Aminosulfonyl, Cyano und Nitro. R1 und R2 sind gleich oder verschieden und stehen vorzugsweise für Wasserstoff, geradkettiges oder verzweigtes Alkyl mit 1 bis 4 Kohlenstoffatomen, Halogen, insbesondere Fluor, Chlor und Brom, Halogenalkyl mit bis zu 3 Kohlenstoff- und bis zu 5 gleichen oder verschiedenen Halogenatomen, wobei als Halogene insbesondere Fluor und Chlor stehen sowie vorzugsweise für gegebenenfalls einfach oder mehrfach substituiertes Phenyl, wobei als Substituenten vorzugsweise die für R genannten Reste infrage kommen.R3 steht vorzugsweise für geradkettiges oder verzweigtes Alkyl mit 1 bis 6, insbesondere 1 bis 4 Kohlenstoffatomen sowie für gegebenenfalls einfach oder mehrfach substituiertes Phenyl, wobei als Substituenten vorzugsweise die bei R bereits genannten Reste sowie Phenyl und Phenoxy, die ebenfalls durch R substituiert sein können, infrage kommen.Formula (II) provides a general definition of the N-acylmethylanilines to be used as starting materials. In this formula, R preferably represents straight-chain or branched alkyl having 1 to 6, in particular 1 to 4, carbon atoms, halogen, in particular fluorine, chlorine and bromine, haloalkyl having up to 3 carbon atoms and up to 5 identical or different halogen atoms, with halogens in particular fluorine and chlorine, for example trifluoromethyl; further preferably for alkylthio and alkylsulfonyl having 1 to 4 carbon atoms in the alkyl part and for aminosulfonyl, cyano and nitro. R 1 and R 2 are identical or different and are preferably hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, halogen, in particular fluorine, chlorine and bromine, haloalkyl with up to 3 carbon atoms and up to 5 identical or different halogen atoms, the halogens being in particular fluorine and chlorine and preferably phenyl which is monosubstituted or polysubstituted, the substituents mentioned for R being preferred R 3 preferably represents straight-chain or branched alkyl having 1 to 6, in particular 1 to 4, carbon atoms and optionally optionally mono- or polysubstituted phenyl, the substituents which are preferably the radicals already mentioned for R and phenyl and phenoxy, which are likewise represented by R may be substituted.

Die N-Acylmethyl-aniline der Formel (II) sind bekannt (vergleiche u.a. Bischler, Chem.Ber. 25, 2865 (1892) sowie Crowther, Mann, Purdie, Chem.Soc. 1943, 63) oder lassen sich nach bekannten Methden herstellen. Man erhält sie z.B., indem man Aniline mit a-Halogenketonen in Gegenwart eines organischen Lösungsmittels, wie z.B. Aethanol, umsetzt (vergleiche auch die Herstellungsbeispiele).The N-acylmethyl-anilines of the formula (II) are known (see, inter alia, Bischler, Chem. Ber. 25, 2865 (1892) and Crowther, Mann, Purdie, Chem. Soc. 1943, 63) or can be prepared by known methods . They are obtained, for example, by anilines with a-haloketones in the presence of an organic solvent, e.g. Ethanol, implemented (see also the manufacturing examples).

Als Verdünnungsmittel kommen für die erfindungsgemäße Umsetzung vorzugsweise inerte organische Lösungsmittel infrage. Hierzu gehören vorzugsweise Ketone, wie Diäthylketon, insbesondere Aceton und Methyläthylketon; Nitrile, wie Propionitril, insbesondere Acetonitril; Aether, wie Tetrahydrofuran oder Dioxan; aliphatische und aromatische Kohlenwasserstoffe, wie Petroläther, Benzol, Toluol oder Xylol; halogenierte Kohlenwasserstoffe, wie Methylenchlorid, Tetrachlorkohlenstoff, Chloroform oder Chlorbenzol; und Ester, wie Essigester.Inert organic solvents are preferably suitable as diluents for the reaction according to the invention. These preferably include ketones, such as diethyl ketone, in particular acetone and methyl ethyl ketone; Nitriles, such as propionitrile, especially acetonitrile; Ethers such as tetrahydrofuran or dioxane; aliphatic and aromatic hydrocarbons, such as petroleum ether, benzene, toluene or xylene; halogenated hydrocarbons such as methylene chloride, carbon tetrachloride, chloroform or chlorobenzene; and esters, such as ethyl acetate.

Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäBen Verfahrens in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man zwischen 0 und 120°C, vorzugsweise zwischen 20 und 100°C.The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, between 0 and 120 ° C, preferably between 20 and 100 ° C.

Bei der Durchführung des erfindungsgemäßen Verfahrens setzt man vorzugsweise auf 1 Mol der Verbindung der Formel (II) 1 bis 3 Mol Chloracetylchlorid ein. Die Isolierung der Verbindungen der Formel (I) erfolgt in üblicher Weise.When carrying out the process according to the invention, 1 to 3 moles of chloroacetyl chloride are preferably used per mole of the compound of the formula (II). The compounds of the formula (I) are isolated in a customary manner.

Die erfindungsgemäßen Wirkstoffe beeinflussen das Pflanzer.- wachstum und können deshalb als Defoliants, Desiccants, Krautabtötungsmittel, Keimhemmungsmittel und insbescndere als Unkrautvernichtungsmittel verwendet werden. Unter Unkraut im weitesten Sinne sind alle Pflanzen zu versteher., die an Orten aufwachsen, wo sie unerwünscht sind. Ob die erfindungsgemäßen Stoffe als totale oder selektive Herbizide wirken, hängt im wesentlichen von der angewendeten Menge ab.The active compounds according to the invention influence the planter growth and can therefore be used as defoliants, desiccants, haulm killers, germ inhibitors and, in particular, as weed killers. Weeds in the broadest sense are all plants that grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

Die erfindungsgemäßen Wirkstoffe können z.B. bei den folgenden Pflanzen verwendet werden:

  • Dikotyle Unkräuter der Gattungen: Senf (Sinapis), Kresse (Lepidium), Labkraut (Galium), Sternmiere (Stellaria), Kamille (Matricaria), Hundskamille (Anthemis), Knopfkraut (Galinsoga), Gänsefuß (Chenopodium), Brennessel (Urtica), Kreuzkraut (Senecio), Fuchsschwanz (Amaranthus), Portulak (Portulaca), Spitzklette (Xanthium), Winde (Convolvulus), Prunkwinde (Ipomoea), Knöterich (Polygonum), Sesbanie (Sesbania), Ambrosie (Ambrosia), Kratzdistel (Cirsium), Distel (Carduus), Gänsedistel (Sonchus), Nachtschatten (Solanum), Sumpfkresse (Rorippa), Rotala, Büchsenkraut (Lindernia), Taubnessel (Lamium), Ehrenpreis (Veronica), Schönmalve (Abutilon), Emex, Stechapfel (Datura), Veilchen (Viola), Hanfnessel, Hohlzahn (Galeopsis), Mohn (Papaver), Flockenblume (Centaurea).
  • Dicotyle Kulturen der Gattungen: Baumwolle (Gossypium), Sojabohne (Glycine), Rübe (Beta), Möhre (Daucus), Gartenbohne (Phaseolus), Erbse (Pisum), Kartoffel (Solanum), Lein (Linum), Prunkwinde (Ipomoea), Bohne (Vicia), Tabak (Nicotiana), Tomate (Lycopersicon), Erdnuß (Arachis), Kohl (Brassica), Lattich (Lactuca), Gurke (Cucumis), Kürbis (Cuburbita).
  • Monokotyle Unkräuter der Gattungen: Hühnerhirse (Echinochloa), Borstenhirse (Setaria), Hirse (Panicum), Fingerhirse (Digitaria), Lieschgras (Phleum), Rispengras (Poa), Schwingel (Festuca), Eleusine, Brachiaria, Lolch (Lolium), Trespe (Bromus), Hafer (Avena), Zypergras (Cyperus), Mohrenhirse (Sorghum), Quecke (Agropyron), Hundszahngras (Cynodon), Monocharia, Fimbristylis, Pfeilkraut (Sagittaria), Sumpfried (Eleocharis.), Simse (Scirpus), Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Straußgras (Agrostis), Fuchsschwanzgras (Alopecurus), Windhalm (Apera).
  • Monokotyle Kulturen der Gattungen: Reis (Oryza), Mais (Zea), Weizen (Triticum), Gerste (Hordeum), Hafer (Avena), Roggen (Secale), Mohrenhirse (Sorghum), Hirse (Panicum), Zuckerrohr (Saccharum), Ananas (Ananas), Spargel (Asparagus), Lauch (Allium).
The active compounds according to the invention can be used, for example, in the following plants:
  • Dicotyledon weeds of the genera: mustard (Sinapis), cress (Lepidium), bedstraw (Galium), starwort (Stellaria), chamomile (Matricaria), dog chamomile (Anthemis), button herb (Galinsoga), goose foot (Chenopodium), nettle (Urtica), Ragwort (Senecio), Foxtail (Amaranthus), Purslane (Portulaca), Norway Burlap (Xanthium), Winch (Convolvulus), Morning Glory (Ipomoea), Knotweed (Polygonum), Sesbanie (Sesbania), Ambrosia (Ambrosia), Scratch Thistle (Cirsium) Thistle (Carduus), Goose Thistle (Sonchus), Nightshade (Solanum), Marsh Cress (Rorippa), Rotala, Ciderweed (Lindernia), Deadnettle (Lamium), Honorary Award (Veronica), Schönmalve (Abutilon), Emex, Stecheapfel (Datura), Violet (Viola), hemp nettle, hollow tooth (galeopsis), poppy (papaver), knapweed (centaurea).
  • Dicot y le cultures of the genera: cotton (Gossypium), soybean (Glycine), turnip (Beta), carrot (Daucus), haricot bean (Phaseolus), pea (Pisum), potato (Solanum), flax (Linum), morning glory (Ipomoea ), Bean (Vicia), tobacco (Nicotiana), tomato (Lycopersicon), peanut (Arachis), cabbage (Brassica), cos (Lactuca), cucumber (Cucumis), pumpkin (Cuburbita).
  • Monocotyledon weeds of the genera: Millet (Echinochloa), Bristle (Setaria), Millet (Panicum), Millet (Digitaria), Lieschgras (Phleum), Panicle Grass (Poa), Fescue (Festuca), Eleusine, Brachiaria, Lolch (Lolch (Lolch (Bromus), oats (Avena), cyper grass (Cyperus), black millet (Sorghum), grasshopper (Agropyron), canine grass (Cynodon), monocharia, fimbristylis, arrow herb (Sagittaria), swamp (Eleocharis.), Cornices (Scirpus), Paspalum , Ischaemum, Sphenoclea, Dactyloctenium, ostrich grass (Agrostis), foxtail grass (Alopecurus), wind straw (Apera).
  • Monocot cultures of the genera: Rice (Oryza), Maize (Zea), Wheat (Triticum), Barley (Hordeum), Oats (Avena), Rye (Secale), Black Millet (Sorghum), Millet (Panicum), Sugar Cane (Saccharum), Pineapple (pineapple), asparagus (asparagus), leek (allium).

Die Verwendung der erfindungsgemäßen Wirkstoffe ist jedoch keineswegs auf diese Gattungen beschränkt, sondern erstreckt sich in gleicher Weise auch auf andere Pflanzen.However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.

Die Verbindungen eignen sich in Abhängigkeit von der Konzentration zur Totalunkrautbekämpfung z.B. auf Industrie- und Gleisanlagen und auf Wegen und Plätzen mit und ohne Baumbewuchs. Ebenso können die Verbindungen zur Unkrautbekämpfung in Dauerkulturen z.B. Forst-, Ziergehölz-, Obst-, Wein-, Citrus-, Nuss-, Bananen-, Kaffee-, Tee-, Gummi-, Ölpalm-, Kakao-, Beerenfrucht- und Hopfenanlagen und zur selektiven Unkrautbekämpfung in einjährigen Kulturen eingesetzt werden.Depending on the concentration, the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops can e.g. Forestry, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annual crops.

Die erfindungsgemäßen Wirkstoffe körnen vorzugsweise zur selektiven Unkraut- und insbesondere Ungräserbekämpfmg in verschiedenen Kulturen eingesetzt werden. Mit den erfindungsgemäßen Wirkstoffen ist es - im Gegensatz zu den als Gräserherbizide bereits bekannten Chloracetaniliden - möglich, neben Dikotylen, z.B. Galinsoga und Sinapis, auch die schwer bekämpfbaren Ungräser Avena fatua oder Alopecurus gleichzeitig mit anderen Schadgräsern, z.B. Digitaria, Echinochloa, Panicum und/oder Setaria in Kulturen, wie Zuckerrüben, Sojabohnen, Bohnen, Baumwolle, Raps, Erdnüssen, GemUsearten, Mais und Reis erfolgreich zu bekämpfen.The active compounds according to the invention can preferably be used for selective weed control and in particular weed control in various crops. With the active compounds according to the invention, it is already - in contrast to those used as grass herbicides known chloroacetanilides - possible, in addition to dicotyledons, e.g. Galinsoga and Sinapis, also the difficult to control weed Avena fatua or Alopecurus at the same time as other harmful grasses, e.g. Digitaria, Echinochloa, Panicum and / or Setaria in crops such as sugar beet, soybeans, beans, cotton, rape , Peanuts, vegetables, corn and rice.

Die erfindungsgemäßen Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Pasten und Granulate. Diese werden in bekannter Weise hergestellt, z. B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel können z. B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, Benzol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chloräthylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z. B. Erdölfraktionen, Alkohole, wie Butanol oder Glycol sowie deren Äther und Ester, Ketone, wie Aceton, Methyläthylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylaulfoxid, sowie Wasser; mit verflüssigten gasförmigen Streokmitteln oder Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z. B. Aerosol-Treibgase, wie Dichlordifluormethan oder Trichlorfluormethan; als feste Trägerstoffe: naturliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate; als Emulgiermittel; nichtionogene und anionische Emulgatoren, wie Polyoxyäthylen-Fettsäure-Ester,Polyoxy- äthylen-Fettalkohol-Äther, z.B. Alkylaryl-polyglycol-Xther, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel: z. B. Lignin -Sulfitablaugen und Methylcellulose.The active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules. These are manufactured in a known manner, e.g. B. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. In the case of the use of water as an extender, e.g. B. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, benzene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylaulfoxide, and water; Liquefied gaseous scattering agents or carriers mean liquids which are gaseous at normal temperature and under normal pressure, e.g. B. aerosol propellants such as dichlorodifluoromethane or trichlorofluoromethane; as solid carriers: natural rock flour, such as kaolins, clays, talc, chalk, Quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates; as an emulsifier; nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as a dispersant: e.g. B. lignin sulfite and methyl cellulose.

Die erfindungsgemäßen Wirkstoffe können als solche oder in ihren Formulierungen zur Verstärkung und Ergänzung ihres Wirkungsspektrums je nach beabsichtigter Verwendung mit anderen herbiziden Wirkstoffen kombiniert werden, wobei Fertigformulierung oder Tankmischung möglich ist.The active compounds according to the invention, as such or in their formulations for strengthening and supplementing their spectrum of action, can be combined with other herbicidal active compounds, depending on the intended use, finished formulation or tank mixture being possible.

Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,5 und 90 Gew.-%.The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90% by weight.

Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Emulsionen, Suspensionen, Pulver, Pasten und Granulate angewendet werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Spritzen, Sprühen, Stäuben, Streuen und Gießen.The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They are used in the usual way, e.g. by spraying, spraying, dusting, scattering and pouring.

Die erfindungsgemäßen Wirkstoffe können sowohl nach als auch insbesondere vor dem Auflaufen der Pflanzen appliziert werden. Sie können auch vor der Saat in den Boden eingearbeitet werden.The active compounds according to the invention can be applied both after and in particular before the plants emerge. They can also be worked into the soil before sowing.

Die aufgewandtewirkatoffmenge kann in größeren Bereichen schwanken. Sie hängt im wesentlichen von der Art des gewünschten Effekts ab. Im allgemeinen liegen die Aufwandmengen zwischen 0,1 und 10 kg Wirkstoff pro ha, vorzugsweise zwischen 0,2 und 5 kg/ha.The amount of active ingredient used can fluctuate in larger areas. It essentially depends on the type of effect you want. In general, the application rates are between 0.1 and 10 kg of active ingredient per ha, preferably between 0.2 and 5 kg / ha.

Die guten herbiziden Wirkungen der erfindungsgemäßen Wirkstoffe und ihre selektiven Einsatzmöglichkeiten gehen aus den nachfolgenden Beispielen hervor.The good herbicidal effects of the active compounds according to the invention and their selective uses are evident from the examples below.

Die erfindungsgemäßen Wirkstoffe können auch mit anderen Herbiziden gemischt werden, z.B. mit Metamitron für Zuckerrüben, mit Metribuzin für Sojabohnen, mit Atrazin für Mais und mit Diuron bzw. Fluomethuron für Baumwolle.The active compounds according to the invention can also be mixed with other herbicides, e.g. with metamitron for sugar beet, with metribuzin for soybeans, with atrazine for corn and with diuron or fluomethuron for cotton.

Beispiel AExample A Pre-emergence-TestPre-emergence test Lösungsmittel: 5 Gewichtsteile Aceton Emulgator: 1 Gewichtsteil AlkylarylpolyglycolätherSolvent: 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether

Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Samen der Testpflanzen werden in normalen Boden ausgesät und nach 24 Stunden mit der Wirkstoffzubereitung begossen. Dabei hält man die Wassermenge pro Flächeneinheit zweckmäßigerweise konstant. Die Wirkstoffkonzentration in der Zubereitung spielt keine Rolle, entscheidend ist nur die Aufwandmenge des Wirkstoffs pro Flächeneinheit. Nach drei Wochen wird der Schädigungsgrad der Pflanzen bonitiert in % Schädigung im Vergleich zur Entwicklung der unbehandelten Kontrolle. Es bedeuten:

  • 0 % = keine Wirkung (wie unbehandelte Kontrolle)
  • 100 % = totale Vernichtung
Seeds of the test plants are sown in normal soil and watered with the preparation of active compound after 24 hours. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
  • 0% = no effect (like untreated control)
  • 100% = total annihilation

Wirkstoffe, Aufwandmengen und Resultate gehen εus der nachfolgenden Tabelle hervor:

Figure imgb0004
Active ingredients, application rates and results are shown in the table below:
Figure imgb0004

HerstellungsbeispieleManufacturing examples Beispiel 1example 1

Figure imgb0005
Figure imgb0005

In eine Lösung von 18,5 g (0,068 Mol) 2,6-Dimethyl-N-(4-chlor- benzoylmethyl)-anilin in 150 ml Benzol werden 16 ml (0,2 Mol) Chloracetylchlorid getropft. Danach läßt man 15 Stunden unter Rückfluß rühren und engt durch Abdestillieren des Lösungsmittels und des überschüssigen Chloracetylchlorids im Vakuum ein. Der Rückstand wird mit einem Gemisch Aether/Petroläther (1 : 3) verrieben, der entstehende kristalline Rückstand abgesaugt und getrocknet. Man erhält 17,7 g (75 % der Theorie) 2,6-Dimethyl-N-(4-chlorbenzoylmethyl)-chloracetanilid vom Schmelzpunkt 128°C.16 ml (0.2 mol) of chloroacetyl chloride are added dropwise to a solution of 18.5 g (0.068 mol) of 2,6-dimethyl-N- (4-chloro-benzoylmethyl) aniline in 150 ml of benzene. The mixture is then stirred under reflux for 15 hours and concentrated by distilling off the solvent and the excess chloroacetyl chloride in vacuo. The residue is triturated with a mixture of ether / petroleum ether (1: 3), the resulting crystalline residue is filtered off with suction and dried. 17.7 g (75% of theory) of 2,6-dimethyl-N- (4-chlorobenzoylmethyl) chloroacetanilide with a melting point of 128 ° C. are obtained.

Herstellung des AusgangsproduktesManufacture of the starting product

Figure imgb0006
Figure imgb0006

46,7 g (0,2 Mol) ω-Brom-4-chloracetophenon in 40 ml Aethanol werden zu 48,4 g (0,4 Mol) 2,6-Dimethylanilin in 40 ml Aethanol gegeben und 20 Minuten auf 50°C erwärmt. Danach kühlt man auf 0°C ab, filtriert die entstandenen Kristalle ab und wäscht mit wenig Aethanol nach. Man erhält 30 g (55 % der Theorie) 2,6-Dimethyl-N-(4-chlorbenzoylmethyl)-anilin vom Schmelzpunkt 82°C.46.7 g (0.2 mol) of ω-bromo-4-chloroacetophenone in 40 ml of ethanol are added to 48.4 g (0.4 mol) of 2,6-dimethylaniline in 40 ml of ethanol and at 50 ° C. for 20 minutes warmed. Then it is cooled to 0 ° C., the crystals formed are filtered off and washed with a little ethanol. 30 g (55% of theory) of 2,6-dimethyl-N- (4-chlorobenzoylmethyl) aniline with a melting point of 82 ° C. are obtained.

Beispiel 2Example 2

Figure imgb0007
Figure imgb0007

23,3 g (0,1 Mol) 2-Aethyl-6-methyl-N-pivaloylmethyl-anilin werden in 100 ml Benzol gelöst und mit 24 ml (0,3 Mol) Chloracetylchlorid versetzt. Danach läßt man 15 Stunden unter Rückfluß rühren und engt durch Abdestillieren des Lösungsmittels und des überschüssigen Chloracetylchlorids im Vakuum ein. Der ölige Rückstand wird mit Petroläther verrührt, dekantiert, mit Aktivkohle verrührt, filtriert und im Vakuum eingeengt. Der Rückstand wird mit n-Hexan verrührt, der resultierende Feststoff abgesaugt und getrocknet. Man erhält 13,7 g (45 % der Theorie) 2-Aethyl-6-methylN-pivaloylmethyl-chloracetanilid vom Schmelzpunkt 86°C.23.3 g (0.1 mol) of 2-ethyl-6-methyl-N-pivaloylmethyl-aniline are dissolved in 100 ml of benzene and mixed with 24 ml (0.3 mol) of chloroacetyl chloride. The mixture is then stirred under reflux for 15 hours and concentrated by distilling off the solvent and the excess chloroacetyl chloride in vacuo. The oily residue is stirred with petroleum ether, decanted, stirred with activated carbon, filtered and concentrated in vacuo. The residue is stirred with n-hexane, the resulting solid is filtered off with suction and dried. 13.7 g (45% of theory) of 2-ethyl-6-methylN-pivaloylmethyl-chloroacetanilide with a melting point of 86 ° C. are obtained.

Herstellung des AusgangsproduktesManufacture of the starting product

Figure imgb0008
Figure imgb0008

108 g (0,8 Mol) 2-Aethyl-6-methyl-anilin und 53,8 g (0,4 Mol, Monochlorpinakolin werden in 300 ml Toluol 25 Stunden auf 110°C erhitzt. Man läßt abkühlen, filtriert, wäscht das Filtrat mit Wasser, trocknet über Natriumsulfat und engt durch Abdestillieren des Lösungsmittels im Vakuum ein. Der Rückstand, wird fraktioniert destilliert. Man erhält 24,1 g (26 % der Theorie) 2-Aethyl-6-methyl-N-pivaloylmethyl-anilin vom Siedepunkt 138-150°C/0,7 mm und einem Brechungsindex von

Figure imgb0009
=1,5168.108 g (0.8 mol) of 2-ethyl-6-methyl-aniline and 53.8 g (0.4 mol, monochloropinacoline are heated in 300 ml of toluene for 25 hours at 110 ° C. The mixture is allowed to cool, filtered and washed Filtrate with water, dried over sodium sulfate and concentrated by distilling off the solvent in vacuo. The residue is fractionally distilled. 24.1 g (26% of theory) of 2-ethyl-6-methyl-N-pivaloylmethyl-aniline from Boiling point 138-150 ° C / 0.7 mm and a refractive index of
Figure imgb0009
 = 1.5168.

In analoger Weise werden die in der nachfolgenden Tabelle 1 aufgeführten Verbindungen hergestellt.

Figure imgb0010
Figure imgb0011
 In analoger Weise können die in der nachfolgenden Tabelle 2 aufgeführten Verbindungen erhalten werden.
Figure imgb0012
 The compounds listed in Table 1 below are prepared in an analogous manner.
Figure imgb0010
Figure imgb0011
 The compounds listed in Table 2 below can be obtained in an analogous manner.
Figure imgb0012

Claims (6)

1.) N-Acylmethyl-chloracetanilide der Formel
Figure imgb0013
in welcher R für Alkyl, Halogen, Halogenalkyl, Alkylthio, Alkylsulfonyl, Aminosulfonyl, Cyano oder Nitro steht, R1 und R2 gleich oder verschieden sind und für Wasserstoff, Alkyl, Halogen, Halogenalkyl oder gegebenenfalls substituiertes Phenyl stehen, R3 für Alkyl oder gegebenenfalls substituiertes Phenyl steht und n für ganze Zahlen von 0 bis 5 steht. 1.) N-Acylmethyl-chloroacetanilides of the formula
Figure imgb0013
 in which R represents alkyl, halogen, haloalkyl, alkylthio, alkylsulfonyl, aminosulfonyl, cyano or nitro, R 1 and R 2 are the same or different and represent hydrogen, alkyl, halogen, haloalkyl or optionally substituted phenyl, R 3 represents alkyl or optionally substituted phenyl and n stands for integers from 0 to 5. 2.) Verfahren zur Herstellung von N-Acylmethyl-chloracetaniliden, dadurch gekennzeichnet, daß man N-Acylmethylaniline der Formel
Figure imgb0014
in welcher R,R1 ,R2,R3 und n die oben angegebene Bedeutung haben.
mit Chloracetylchlorid in Gegenwart eines Verdünnungsmittels umsetzt.2.) Process for the preparation of N-acylmethyl-chloroacetanilides, characterized in that N-acylmethylanilines of the formula
Figure imgb0014
 in which R, R 1 , R 2 , R 3 and n have the meaning given above.
reacted with chloroacetyl chloride in the presence of a diluent. 3.) Herbizide Mittel, gekennzeichnet durch einen Gehalt an N-Acylmethyl-chloracetaniliden gemäß Anspruch 1.3.) Herbicidal agents, characterized by a content of N-acylmethyl-chloroacetanilides according to claim 1. 4.) Verfahren zur Bekämpfung von unerwünschtem Pflanzenwachstum, dadurch gekennzeichnet, daß man N-Acylmethyl-chloracetanilide gemäß Anspruch 1 auf die unerwünschten Pflanzen oder ihren Lebensraum einwirken läßt.4.) Process for combating undesirable plant growth, characterized in that N-acylmethyl-chloroacetanilides according to claim 1 are allowed to act on the undesired plants or their habitat. 5.) Verwendung von N-Acylmethyl-chloracetaniliden gemäß Anspruch 1 zur Bekämpfung von unerwünschtem Pflanzenwachstum.5.) Use of N-acylmethyl-chloroacetanilides according to claim 1 for combating undesirable plant growth. 6.) Verfahren zur Herstellung von herbiziden Mitteln, dadurch gekennzeichnet, daß man N-Acylmethyl-chloracetanilide gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Mitteln vermischt.6.) Process for the preparation of herbicidal compositions, characterized in that N-acylmethyl-chloroacetanilides according to Claim 1 are mixed with extenders and / or surface-active agents.
EP78100091A 1977-06-10 1978-06-05 N-acylmethyl-chloroacetanilides, process for their preparation and their use as herbicides. Expired EP0000051B1 (en)

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US4260410A (en) * 1978-03-31 1981-04-07 Chevron Research Company Herbicidal and plant-growth-regulating N-haloacetylphenylamino carbonyl oximes
EP0006541A2 (en) * 1978-06-28 1980-01-09 Bayer Ag Use of N,N-diallyl-dichloroacetamide for improving the protection of crop plants against herbicidally active acetanilides
EP0006542A2 (en) * 1978-06-28 1980-01-09 Bayer Ag The use of N-dichloroacetyl-1,2,3,4-tetrahydroisoquinolin as antidote for the protection of cultivated plants against damage caused by herbicidally active acetanilides; combinations thus obtained and process for their preparation
EP0006542A3 (en) * 1978-06-28 1980-01-23 Bayer Ag The use of n-dichloroacetyl-1,2,3,4-tetrahydroisoquinolin as antidote for the protection of cultivated plants against damage caused by herbicidally active acetanilides; combinations thus obtained and process for their preparation
EP0006541A3 (en) * 1978-06-28 1980-01-23 Bayer Ag Use of n,n-diallyl-dichloroacetamide for improving the protection of crop plants against herbicidally active acetanilides
EP0056589A1 (en) * 1981-01-21 1982-07-28 Bayer Ag N-substituted anilides, process for their preparation and their use as fungicides
EP0454067A1 (en) * 1990-04-24 1991-10-30 ZAMBON GROUP S.p.A. Compositions having herbicidal activity containing N-Alkyl-amides as active ingredient
US5336664A (en) * 1990-04-24 1994-08-09 Zambon Group S.P.A. Compositions having herbicidal activity containing N-alkyl-amides as active ingredient
US5556829A (en) * 1990-04-24 1996-09-17 Zambon Group S.P.A. Compositions having herbicidal activity containing N-alkyl-amides as active ingredient
US20150086755A1 (en) * 2012-06-04 2015-03-26 Canon Kabushiki Kaisha Photocured product
US20170129033A1 (en) * 2014-07-14 2017-05-11 Gce Holding Ab Machine cutting torch system

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PL207470A1 (en) 1979-02-26
CS196431B2 (en) 1980-03-31
PL109941B1 (en) 1980-06-30
IT7824355A0 (en) 1978-06-08
TR19764A (en) 1979-11-30
IL54872A (en) 1981-09-13
DD137878A5 (en) 1979-10-03
DE2860162D1 (en) 1980-12-18
ES470665A1 (en) 1979-02-01
AU3677378A (en) 1979-12-06
IL54872A0 (en) 1978-08-31
DK258478A (en) 1978-12-11
JPS545926A (en) 1979-01-17
ZA783329B (en) 1979-06-27
DE2726253A1 (en) 1978-12-21
BR7803711A (en) 1979-01-16
EP0000051B1 (en) 1980-09-17
PT68147A (en) 1978-07-01
NZ187478A (en) 1979-11-01

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