EP0000051B1 - N-acylméthyl-chloroacétanilides, procédé pour leur préparation et leur utilisation comme herbicides. - Google Patents

N-acylméthyl-chloroacétanilides, procédé pour leur préparation et leur utilisation comme herbicides. Download PDF

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Publication number
EP0000051B1
EP0000051B1 EP78100091A EP78100091A EP0000051B1 EP 0000051 B1 EP0000051 B1 EP 0000051B1 EP 78100091 A EP78100091 A EP 78100091A EP 78100091 A EP78100091 A EP 78100091A EP 0000051 B1 EP0000051 B1 EP 0000051B1
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EP
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Prior art keywords
chloroacetanilides
acylmethyl
alkyl
preparation
formula
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP78100091A
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German (de)
English (en)
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EP0000051A1 (fr
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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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
  • DT-OS 2 328 340 grass-like weeds
  • FR-PS 2,216,916 discloses chloroacetanilides in which the nitrogen atom, in addition to the substituted phenyl ring and the chloroacetyl group, is also linked to a radical designated as -A-OR, the group designated as "A" being mandatory for one, if appropriate - Or is twice substituted by methyl-substituted ethylene unit. Substances in which the relevant part of the molecule means an optionally substituted methylene unit are not mentioned. Otherwise, the substances listed in FR-PS 2 216 916 in the aniline portion in the 2- and 6-position of the phenyl ring cannot simultaneously carry alkyl radicals.
  • N-acylmethylchloroacetanilides according to the invention are superior to the previously known chloroacetanilides, such as, for example, 2-ethyl-6-methyl-N- (1'methyl-2'-methoxy-ethyl) -chloroacetanilide, in addition to the grasses Setaria, Lolium and Echinochloa especially Sinapis is better captured. They also show better selectivity in important crops.
  • the active compounds according to the invention thus represent a substantial enrichment of the herbicidal compositions.
  • N-acylmethylchloroacetanilides according to the invention differ constitutionally from the substances known from French Pat -Tied part.
  • the part of the molecule in question is in each case a methoxy or ethoxy group which is bonded via an optionally mono- or disubstituted by methyl-substituted ethylene unit, while the corresponding part of the molecule in the substances according to the invention each represents an optionally substituted methylene group.
  • the N-acylmethyl-chloroacetanilides according to the invention also differ from the substances mentioned in French Patent 2,216,916 with regard to the substitution pattern in the anilide tell, because in the case of the previously known substances, the 2- and 6-position of the phenyl ring cannot be simultaneously occupied by alkyl .
  • the substances described in US Pat. No. 3,966,811 are - acetals, whereas the compounds according to the invention contain an alkylcarbonyl or phenylcarbonyl group at the point in question.
  • Formula (11) provides a general definition of the N-acylmethylanilines to be used as starting materials.
  • 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 'and R 2 are the same 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 having up to 3 carbon and up to 5 identical or different halogen atoms, where as halogens are in particular fluorine and chlorine and preferably for optionally mono- or polysubstituted phenyl, preference being given as substituents. as the residues mentioned for R come into question.
  • 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 can also be substituted by R. , come into question.
  • N-acylmethyl-anilines of the formula (11) are known (compare, 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, especially 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, especially 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 plant 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 understood to mean 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 active compounds according to the invention can e.g. used 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 ), Stinging nettle (Urtica), ragwort (Senecio), foxtail (Amaranthus), purslane (Portulaca), burdock (Xanthium), winch (Convolvulus), morning glory (Ipomoea), knotweed (Polygonum), sesbanie (Sesbania), ambrosia (Ambrosia) ), Thistle (Cirsium), Thistle (Carduus), Goose Thistle (Sonchus), Nightshade (Solanum), Marsh Cress (Rorippa), Rotala, Creeper
  • Monocot crops of the genera Rice (Oryza), Maize (Zea), Wheat (Triticum), Barley (Hordeum), Oats (Avena), Rye (Secale), Black Millet (Sorghum), Millet (Panicum), Sugar Cane (Saccharum), Pineapple (aranas), asparagus (asparagus), leek (allium).
  • 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 weed control connections in permanent crops 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 make it possible, in addition to dicotyledons, e.g. Galinsoga and Sinapis, also the difficult to control weed Avena fatua or Alopecurus at the same time with other harmful grasses, e.g. To successfully combat Digitaria, Echinochloa, Panicum and / or Setaria in crops such as sugar beet, soybeans, beans, cotton, rapeseed, 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 made in a known manner, e.g. 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. If water is used as an extender, e.g. 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.
  • 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 formulations or tank mixes 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.
  • 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.

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (5)

1. Des N-acylméthyl-chloracétanilides de formule:
Figure imgb0014
dans laquelle:
R est un groupe alkyl, un halogène, un groupe halogènalkyle, alkylthio, alkylsulfonyle, aminosulfonyle,, cyano ou nitro,
R1 et R2 sont égaux ou différents et représentent de l'hydrogène, un groupe alkyle, un halogène, un groupe halogénalkyle ou un groupe phényle éventuellement substitué,
R3 est un groupe alkyle ou un groupe phényle éventuellement substitué, et
n représente les nombres entiers de 0 à 5.
2. Procédé de production de N-acylméthyl-chloracétanilides, caractérisé en ce qu'on fait réagir des N-acyl-méthylanilines de formule:
Figure imgb0015
dans laquelle R, R', R2, R3 et n ont les définitions données ci-dessus, avec le chlorure de chloracétyle en présence d'un diluant.
3. Compositions herbicides, caractérisées par une teneur en N-acylméthyl-chloracétanilides suivant la revendication 1.
4. Utilisation des N-acylméthyl-chloracétanilides suivant la revendication 1 pour la lutte contre une croissance végétale non désirée.
5. Procédé de production de compositions herbicides, caractérisé en ce qu'on mélange des N-acylméthyl-chloracétanilides suivant la revendication 1 avec des diluants et/ou des agents tensio-actifs.
EP78100091A 1977-06-10 1978-06-05 N-acylméthyl-chloroacétanilides, procédé pour leur préparation et leur utilisation comme herbicides. Expired EP0000051B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772726253 DE2726253A1 (de) 1977-06-10 1977-06-10 N-acylmethyl-chloracetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
DE2726253 1977-06-10

Publications (2)

Publication Number Publication Date
EP0000051A1 EP0000051A1 (fr) 1978-12-20
EP0000051B1 true EP0000051B1 (fr) 1980-09-17

Family

ID=6011220

Family Applications (1)

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EP78100091A Expired EP0000051B1 (fr) 1977-06-10 1978-06-05 N-acylméthyl-chloroacétanilides, procédé pour leur préparation et leur utilisation comme herbicides.

Country Status (16)

Country Link
EP (1) EP0000051B1 (fr)
JP (1) JPS545926A (fr)
AU (1) AU3677378A (fr)
BR (1) BR7803711A (fr)
CS (1) CS196431B2 (fr)
DD (1) DD137878A5 (fr)
DE (2) DE2726253A1 (fr)
DK (1) DK258478A (fr)
ES (1) ES470665A1 (fr)
IL (1) IL54872A (fr)
IT (1) IT7824355A0 (fr)
NZ (1) NZ187478A (fr)
PL (1) PL109941B1 (fr)
PT (1) PT68147A (fr)
TR (1) TR19764A (fr)
ZA (1) ZA783329B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4260410A (en) * 1978-03-31 1981-04-07 Chevron Research Company Herbicidal and plant-growth-regulating N-haloacetylphenylamino carbonyl oximes
DE2828303A1 (de) * 1978-06-28 1980-01-17 Bayer Ag Verwendung von n,n-diallyl-dichloracetamid zur verbesserung der kulturpflanzen- vertraeglichkeit von herbizid wirksamen acetaniliden
DE2828222A1 (de) * 1978-06-28 1980-01-10 Bayer Ag Gegenmittel zum schutz von kulturpflanzen vor schaedigungen durch herbizide
DE2965415D1 (en) * 1978-11-03 1983-06-16 Bayer Ag Anilinomethyloxime ethers and processes for their production
DE3004871A1 (de) * 1980-02-09 1981-08-20 Bayer Ag, 5090 Leverkusen Halogenalkylamide, verfahren zu deren herstellung und deren verwendung als gegenmittel zum schutz von kulturpflanzen vor schaedigungen durch herbizide
DE3101785A1 (de) * 1981-01-21 1982-08-26 Bayer Ag, 5090 Leverkusen N-substituierte anilide, verfahreen zu ihrer herstellung sowie ihre verwendung als fungizide
US4734119A (en) 1983-11-15 1988-03-29 Ciba-Geigy Corporation Novel phosphorus compounds for protecting cultivated plants from the phytotoxic action of herbicides
IT1240676B (it) * 1990-04-24 1993-12-17 Agrimont Spa Composizioni ad attivita' erbicida
JP6071255B2 (ja) * 2012-06-04 2017-02-01 キヤノン株式会社 光硬化物
EP3169469A1 (fr) * 2014-07-14 2017-05-24 GCE Holding AB Système de chalumeau d'oxycoupage d'une machine

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH579348A5 (fr) * 1973-02-08 1976-09-15 Ciba Geigy Ag
US3966811A (en) * 1974-12-19 1976-06-29 Velsicol Chemical Corporation Dialkyl acetals of anilinoacetaldehydes

Also Published As

Publication number Publication date
TR19764A (tr) 1979-11-30
DK258478A (da) 1978-12-11
PT68147A (de) 1978-07-01
IL54872A (en) 1981-09-13
PL207470A1 (pl) 1979-02-26
PL109941B1 (en) 1980-06-30
IL54872A0 (en) 1978-08-31
CS196431B2 (en) 1980-03-31
BR7803711A (pt) 1979-01-16
DD137878A5 (de) 1979-10-03
EP0000051A1 (fr) 1978-12-20
DE2860162D1 (en) 1980-12-18
ES470665A1 (es) 1979-02-01
JPS545926A (en) 1979-01-17
ZA783329B (en) 1979-06-27
IT7824355A0 (it) 1978-06-08
DE2726253A1 (de) 1978-12-21
AU3677378A (en) 1979-12-06
NZ187478A (en) 1979-11-01

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