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CH576945A5 - Haloacetanilides - selective herbicides - Google Patents

Haloacetanilides - selective herbicides

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Publication number
CH576945A5
CH576945A5 CH728372A CH728372A CH576945A5 CH 576945 A5 CH576945 A5 CH 576945A5 CH 728372 A CH728372 A CH 728372A CH 728372 A CH728372 A CH 728372A CH 576945 A5 CH576945 A5 CH 576945A5
Authority
CH
Switzerland
Prior art keywords
sep
torr
xylidine
formula
radical
Prior art date
Application number
CH728372A
Other languages
German (de)
Original Assignee
Ciba Geigy Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to BE795021D priority Critical patent/BE795021A/en
Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag
Priority to CH728372A priority patent/CH576945A5/en
Priority to SE7301032A priority patent/SE400775B/en
Priority to IL41414A priority patent/IL41414A/en
Priority to SU7301882613A priority patent/SU581836A3/en
Priority to CA162,480A priority patent/CA1047532A/en
Priority to NL7301481.A priority patent/NL161133B/en
Priority to AU51675/73A priority patent/AU470433B2/en
Priority to BG022621A priority patent/BG20534A3/en
Priority to DE19732305495 priority patent/DE2305495C3/en
Priority to DD168667A priority patent/DD103122A5/xx
Priority to YU290/73A priority patent/YU39295B/en
Priority to RO73102519A priority patent/RO80063A/en
Priority to PH14315A priority patent/PH10362A/en
Priority to GB574073A priority patent/GB1422473A/en
Priority to OA54825A priority patent/OA04526A/en
Priority to AT102373A priority patent/AT321639B/en
Priority to PL1973179610A priority patent/PL93822B1/en
Priority to ES411328A priority patent/ES411328A1/en
Priority to HUCI1337A priority patent/HU165898B/hu
Priority to IT20087/73A priority patent/IT983445B/en
Priority to JP1512273A priority patent/JPS5614083B2/ja
Priority to EG48/73A priority patent/EG10663A/en
Priority to PL1973160616A priority patent/PL89203B1/en
Priority to DK62273AA priority patent/DK140531B/en
Priority to FR7304098A priority patent/FR2171171B1/fr
Priority to TR17988A priority patent/TR17988A/en
Priority to CS906A priority patent/CS168627B2/cs
Priority to IN1037/CAL/73A priority patent/IN138952B/en
Priority to AR248005A priority patent/AR231052A1/en
Priority to BR3548/73A priority patent/BR7303548D0/en
Priority to CU33904A priority patent/CU33904A/en
Priority to AT328274A priority patent/AT338249B/en
Priority to US05/548,042 priority patent/US3952056A/en
Priority to SU7502163132A priority patent/SU580831A3/en
Priority to US05/653,556 priority patent/US4019894A/en
Priority to DK201976A priority patent/DK201976A/en
Priority to DK201776A priority patent/DK142161B/en
Priority to US05/688,868 priority patent/US4283221A/en
Publication of CH576945A5 publication Critical patent/CH576945A5/en
Priority to JP52114515A priority patent/JPS5835502B2/en
Priority to US05/905,835 priority patent/US4160660A/en
Priority to US05/944,816 priority patent/US4412855A/en

Links

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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms

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

Abstract

Title cpds. are of formula I: where R' = H or Me; R2 = Me, Et, Pr', Prn, allyl, methallyl, crotyl, cyclopropyl, or cyclopropyl-CH2-; A = CH2CH2- opt. subst. by Et or 1 or 2 Me; and X = Cl or Br. I are prepd. e.g. by condensing an N-substd. aniline with a sensitive haloacetyl deriv.

Description

       

  
 



   Das CH-Hauptpatent Nr. 563963 betrifft ein Verfahren zur Herstellung neuer, herbizid wirksamer Chloracetanilide der Formel
EMI1.1     
 worin R Methyl, Äthyl, n-Propyl oder Isopropyl bedeutet.



   Es wurde nun gefunden, dass dieses Verfahren für die Herstellung analog gebauter Chloracetanilide mit ebenfalls hervorragenden herbiziden Eigenschaften angewendet werden kann.



   Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von neuen N-substituierten Chloracetaniliden der Formel I
EMI1.2     
 worin A einen geradkettigen oder verzweigten Alkylenrest mit 2 bis 4 Kohlenstoffatomen bedeutet, von denen 2 Kohlenstoffatome glieder der Alkylenkette sind, und
R einen Alkenylrest mit 3 oder 4 Kohlenstoffatomen oder den Cyclopropyl- oder Cyclopropylmethylrest darstellt, und falls A einen verzweigten Alkylenrest bedeutet, auch ein Alkylrest mit 1 bis 3 Kohlenstoffatomen sein kann.



   Als Alkylenreste A kommen der geradkettige Äthylenrest (CH2   -      CH2 -),    sowie der verzweigte,   dh.    durch Methyl oder Äthyl substituierte Äthylenrest in Betracht.



   Ein Alkenylrest R ist Allyl oder Methallyl; falls R bei Vorhandensein eines verzweigten Alkylenrestes A auch Alkyl bedeutet, so sind damit Methyl, Äthyl, n-Propyl und Isopropyl gemeint.



   Die neuen Chloracetanilide der Formel I werden erfindungsgemäss hergestellt, indem man ein N-substituiertes Anilin der Formel II
EMI1.3     
 mit einem Chloracetylierungsmittel, vorzugsweise einem Anhydrid oder Halogenid der Chloressigsäure acyliert. In Formel II haben A und R die unter Formel I angegebenen Bedeutungen.



   Die   Uriisetzungen    können in An- oder Abwesenheit von gegen über den Reaktionsteilnehmern inerten Lösungs- oder Verdünnungsmitteln durchgeführt werden. Es kommen beispielsweise folgende in Frage: aliphatische, aromatische oder halogenierte Kohlenwasserstoffe, wie Benzol, Toluol, Xylole, Petroläther, Chlorbenzol, Methylenchlorid, Äthylenchlorid, Chloroform; Äther und ätherartige Verbindungen, wie Dialkyläther, Dioxan, Tetrahydrofuran; Nitrile wie Acetonitril, N,N-dialkylierte Amide wie Dimethylformamid; ferner Dimethylsulfoxid sowie Gemische dieser Lösungsmittel untereinander.



   Als geeignete Chloracetylierungsmittel werden vorzugsweise Chloressigsäureanhydrid und Chloressigsäurehalogenide wie Chloracetylchlorid verwendet. Die Reaktion kann jedoch auch mit Chloressigsäure selbst, ihren Estern oder Amiden durchgeführt werden. Die Reaktionstemperaturen liegen zwischen 0 und 200 C vorzugsweise zwischen 20 und   100 C.    In manchen Fällen, insbesondere bei der Verwendung von Chloracetylhalogeniden, wird die Chloracetylierung in Gegenwart eines säurebindenden Mittels durchgeführt. Als solche kommen tertiäre Amine, wie Trialkylamine, z.B. Triäthylamin, Pyridin und Pyridinbasen, oder anorganische Basen, wie die Oxide und Hydroxide, Hydrogencarbonate und Carbonate von Alkali- und Erdalkalimetallen in Betracht.

  Als säurebindendes Mittel kann ausserdem das jeweilige Anilin der Formel II dienen, welches in diesem Fall im Überschuss angewandet werden muss.



   Einige Ausgangstoffe der Formel II sowie die entsprechenden Hydroxyalkylderivate (R=H) sind bekannt, z.B. aus USP 2381071, 2759943 sowie Am. Soc. 84, 734 und Bull. Soc. Chim. France 1962, 303 und 1965, 2037. Diese sowie in der Literatur noch nicht beschriebene Ausgangstoffe, welche unter die allgemeine Formel II fallen, können nach an sich bekannten Methoden leicht hergestellt werden, wie zum Beispiel: a) Durch Kondensation des entsprechenden methylierten Anilins mit einem Alkanal   OHC - A - OR    zum entsprechenden   R-O-alkylidenaminobenzol    und anschliessende katalytische Hydrierung.



   b) Durch Umsetzung des Methylanilins mit einer Verbindung der Formel III
Y-A-OR   (III)    worin A und R wie unter Formel I definiert sind und Y ein Halogenatom oder einen anderen Säurerest, insbesondere einen Arylsulfonsäurerest darstellt. Verbindungen der Formel III mit Benzolsulfonsäureresten Y sind beispielsweise in Can. J. Chem.



  33, 1207, solche mit Tosyloxyresten   (CH3 -C6H4-SO3 -)    im Brit. Patent 869083 beschrieben.



   Selbstverständlich gibt es noch eine Reihe anderer Verfahren zur Herstellung der Ausgangsstoffe der Formel II aus orthomethylierten Anilinen.



   Das folgende Beispiel veranschaulicht das erfindungsgemässe Verfahren mit Einschluss der Herstellung eines Ausgangsstoffes.



  Weitere Verbindungen der Formel I, die nach dem erfindungsgemässen Verfahren hergestellt wurden, sind in der anschliessenden Tabelle aufgeführt Temperaturen beziehen sich auf Celsiusgrade.



  Beispiel: a) Herstellung der Ausgangsverbindung
Eine Lösung von 484 g (4 Mole) 2,6-Xylidin und 490 g (2 Mole)   p-Toluolsulfonsäure.(1-methoxyprop-2.yl)-ester    in 1000 ml Toluol wird 25 Std. am Rückfluss erhitzt. Das abgekühlte Reaktionsgemisch wird dann alkalisch gemacht und mit Diäthyläther verdünnt. Die organische Phase wird mehrfach mit Wasser gewaschen und über Mg-Sulfat getrocknet. Nach dem Abdestillieren des Lösungsmittels und weiterer Destillation erhält man   N-(1'-methoxyprop-2'-yl)-2,6-xylidin,    Kp.   70-72 C/0.4    Torr.



  b) Herstellung von   N-(l '-Methoxyprop-2'-yl)-N-chloracetyl-2,6-       dimethylantlin   
Unter Rühren wird zu einer Suspension, bestehend aus 42,5 g (0,22 Mol) des unter a) erhaltenen Zwischenprodukts, 23,3 g (0,22 Mol) Na- Carbonat und 300 ml Benzol (absolut), tropfenweise eine Lösung von 26,0 g (0,23 Mol) Chloracetylchlorid in 50 ml Benzol (absolut) getropft. Danach wird die Mischung 2   Std.   



  bei Raumtemperatur weitergerührt. Nach dem Verdünnen mit Diäthyläther wird die organische Phase wiederholt mit Wasser gewaschen, getrocknet und im Vakuum eingeengt. Das kristalline Endprodukt schmilzt nach dem Umkristallisieren bei   44-46     C.



   In der folgenden Tabelle sind diese sowie weitere nach dem im Beispiel beschriebenen Verfahren hergestellte Verbindungen der Formel 1 zusammengestellt.  



   Die erfindungsgemässen Wirkstoffe sind stabile Verbindungen und besitzen sehr gute herbizide Eigenschaften gegen Gramineen, wie Hirse und hirseartige Pflanzen der Gattungen Setaria, Digitaria etc., gegen Gräser wie Loliumarten und auch gegen viele dikotyle Unkrautarten, wie Amaranthus, Sesbania, Chrysanthemum, Ipomea, Galium, Pastinak etc., ohne dass Kulturpflanzen wie Sojabohnen, Bohnen, Erbsen, Mais, Baumwolle, Luzerne geschädigt werden.



   Die Applikation der Wirkstoffe erfolgt entweder vor oder nach dem Auflaufen der Kulturpflanzen und der Unkräuter und Ungräser, vorzugsweise vor dem Auflaufen. Die Aufwandmengen liegen zwischen 0,1 und 10 kg Wirkstoff pro Hektar, wobei im Vorauflauf schon mit einer Aufwandmenge von 0,5 kg/ha eine sehr weitgehende Vernichtung der Unkräuter erzielt wird.

 

   Ausserdem zeigen einige der neuen Wirkstoffe der Formel I auch wachstumsregulierende Eigenschaften, indem sie z.B. in bestehenden Rasenkulturen das Längenwachstum des Rasens verzögern und die Bestockung erhöhen.



   Es wurde überraschenderweise gefunden, dass die Wirkstoffe der Formel I dem als Spitzenprodukt unter den N-Alkoxyalkyl50 55 60 65 halogenacetaniliden des Handels geltenden N-Methoxymethyl-2,6diäthylchloracetanilid (Handelsname: Alachlor) in der Unkrautbekämpfung überlegen sind und auf Grund grösserer chemischer Stabilität eine bessere Dauerwirkung im Erdboden entfalten. 



  
 



   CH main patent no. 563963 relates to a process for the preparation of new, herbicidally active chloroacetanilides of the formula
EMI1.1
 wherein R is methyl, ethyl, n-propyl or isopropyl.



   It has now been found that this process can be used for the production of analogously constructed chloroacetanilides with likewise excellent herbicidal properties.



   The present invention relates to a process for the preparation of new N-substituted chloroacetanilides of the formula I.
EMI1.2
 wherein A is a straight-chain or branched alkylene radical having 2 to 4 carbon atoms, of which 2 carbon atoms are members of the alkylene chain, and
R represents an alkenyl radical with 3 or 4 carbon atoms or the cyclopropyl or cyclopropylmethyl radical, and if A represents a branched alkylene radical, it can also be an alkyl radical with 1 to 3 carbon atoms.



   As alkylene radicals A, the straight-chain ethylene radical (CH2 - CH2 -), as well as the branched one, ie. Ethylene radical substituted by methyl or ethyl can be considered.



   An alkenyl radical R is allyl or methallyl; if R also denotes alkyl in the presence of a branched alkylene radical A, this denotes methyl, ethyl, n-propyl and isopropyl.



   The new chloroacetanilides of the formula I are prepared according to the invention by adding an N-substituted aniline of the formula II
EMI1.3
 acylated with a chloroacetylating agent, preferably an anhydride or halide of chloroacetic acid. In formula II, A and R have the meanings given under formula I.



   The reactions can be carried out in the presence or absence of solvents or diluents which are inert towards the reactants. For example, the following are possible: aliphatic, aromatic or halogenated hydrocarbons, such as benzene, toluene, xylenes, petroleum ether, chlorobenzene, methylene chloride, ethylene chloride, chloroform; Ethers and ethereal compounds such as dialkyl ethers, dioxane, tetrahydrofuran; Nitriles such as acetonitrile, N, N-dialkylated amides such as dimethylformamide; also dimethyl sulfoxide and mixtures of these solvents with one another.



   Suitable chloroacetylating agents are preferably chloroacetic anhydride and chloroacetic acid halides such as chloroacetyl chloride. However, the reaction can also be carried out with chloroacetic acid itself, its esters or amides. The reaction temperatures are between 0 and 200 ° C., preferably between 20 and 100 ° C. In some cases, especially when using chloroacetyl halides, the chloroacetylation is carried out in the presence of an acid-binding agent. As such, tertiary amines such as trialkylamines, e.g. Triethylamine, pyridine and pyridine bases, or inorganic bases, such as the oxides and hydroxides, hydrogen carbonates and carbonates of alkali and alkaline earth metals.

  The respective aniline of the formula II, which in this case must be used in excess, can also serve as the acid-binding agent.



   Some starting materials of the formula II and the corresponding hydroxyalkyl derivatives (R = H) are known, e.g. from USP 2381071, 2759943 and Am. Soc. 84, 734 and Bull. Soc. Chim. France 1962, 303 and 1965, 2037. These starting materials, which have not yet been described in the literature and which come under the general formula II, can easily be prepared by methods known per se, such as, for example: a) By condensation of the corresponding methylated aniline with an alkanal OHC - A - OR to the corresponding RO-alkylideneaminobenzene and subsequent catalytic hydrogenation.



   b) By reacting the methylaniline with a compound of the formula III
Y-A-OR (III) where A and R are as defined under formula I and Y represents a halogen atom or another acid radical, in particular an arylsulfonic acid radical. Compounds of the formula III with benzenesulfonic acid radicals Y are for example in Can. J. Chem.



  33, 1207, those with tosyloxy residues (CH3 -C6H4-SO3 -) in Brit. Patent 869083.



   There are of course a number of other processes for preparing the starting materials of the formula II from orthomethylated anilines.



   The following example illustrates the process according to the invention including the production of a starting material.



  Further compounds of the formula I which were prepared by the process according to the invention are listed in the table below. Temperatures relate to degrees Celsius.



  Example: a) Preparation of the starting compound
A solution of 484 g (4 moles) of 2,6-xylidine and 490 g (2 moles) of p-toluenesulfonic acid. (1-methoxyprop-2.yl) ester in 1000 ml of toluene is refluxed for 25 hours. The cooled reaction mixture is then made alkaline and diluted with diethyl ether. The organic phase is washed several times with water and dried over magnesium sulfate. After distilling off the solvent and further distillation, N- (1'-methoxyprop-2'-yl) -2,6-xylidine, boiling point 70-72 C / 0.4 Torr, is obtained.



  b) Preparation of N- (l'-methoxyprop-2'-yl) -N-chloroacetyl-2,6-dimethylantline
With stirring, a solution is added dropwise to a suspension consisting of 42.5 g (0.22 mol) of the intermediate obtained under a), 23.3 g (0.22 mol) of sodium carbonate and 300 ml of benzene (absolute) of 26.0 g (0.23 mol) of chloroacetyl chloride in 50 ml of benzene (absolute) were added dropwise. Then the mixture is 2 hours.



  stirred further at room temperature. After dilution with diethyl ether, the organic phase is washed repeatedly with water, dried and concentrated in vacuo. The crystalline end product melts after recrystallization at 44-46 C.



   These and other compounds of the formula 1 prepared by the process described in the example are compiled in the following table.



   The active ingredients according to the invention are stable compounds and have very good herbicidal properties against gramineae, such as millet and millet-like plants of the genera Setaria, Digitaria, etc., against grasses such as lolium species and also against many dicotyledonous weed species such as Amaranthus, Sesbania, Chrysanthemum, Ipomea, Galium, Parsnip, etc., without damaging crops such as soybeans, beans, peas, corn, cotton, alfalfa.



   The active compounds are applied either before or after emergence of the crop plants and the weeds and grass weeds, preferably before emergence. The application rates are between 0.1 and 10 kg of active ingredient per hectare, with an application rate of 0.5 kg / ha already achieving very extensive destruction of the weeds in the pre-emergence phase.

 

   In addition, some of the new active ingredients of the formula I also show growth-regulating properties, e.g. Delay the growth of the length of the lawn in existing lawn crops and increase the tillering.



   It has surprisingly been found that the active ingredients of the formula I are superior to N-methoxymethyl-2,6-diethylchloroacetanilide (trade name: Alachlor) in weed control and are superior to N-methoxymethyl-2,6-diethylchloroacetanilide (trade name: Alachlor) as the top product among the N-alkoxyalkyl50 55 60 65 halogenacetanilides in weed control, and because of their greater chemical stability develop a better permanent effect in the ground.

Claims (1)

PATENTANSPRUCH PATENT CLAIM Verfahren zur Herstellung substituierter Chloracetanilide der FormelI EMI2.1 worin A einen geradkettigen oder verzweigten Alkylenrest mit 2 bis 4 Kohlenstoffatomen bedeutet, von denen 2 Kohlenstoffatome Verb. -A-OR Physikalische No. Daten EMI2.2 <tb> <SEP> 1 <SEP> -CH-CH2-O-CH2-CH=CH2 <SEP> n <SEP> 1.5353 <tb> <SEP> 2 <SEP> -CHz <SEP> -CH2 <SEP> -O-CH-CH <SEP> =CH2 <SEP> ndo <SEP> 1.5368 <tb> <SEP> H3 <tb> <SEP> 3 <SEP> -CH2-CH2-O-(I <SEP> -nr2X3 <SEP> 1.5362 <tb> <SEP> 4 <SEP> -CH2-CH2-O-CH2-a <SEP> nD23 <SEP> 1.5324 <tb> <SEP> 5 <SEP> CH- <SEP> CH2-O-CH3 <SEP> Smp. Process for the preparation of substituted chloroacetanilides of the formula I. EMI2.1 wherein A is a straight-chain or branched alkylene radical having 2 to 4 carbon atoms, of which 2 carbon atoms are Verb. -A-OR Physical No. Data EMI2.2 <tb> <SEP> 1 <SEP> -CH-CH2-O-CH2-CH = CH2 <SEP> n <SEP> 1.5353 <tb> <SEP> 2 <SEP> -CHz <SEP> -CH2 <SEP> -O-CH-CH <SEP> = CH2 <SEP> ndo <SEP> 1.5368 <tb> <SEP> H3 <tb> <SEP> 3 <SEP> -CH2-CH2-O- (I <SEP> -nr2X3 <SEP> 1.5362 <tb> <SEP> 4 <SEP> -CH2-CH2-O-CH2-a <SEP> nD23 <SEP> 1.5324 <tb> <SEP> 5 <SEP> CH- <SEP> CH2-O-CH3 <SEP> Smp. <SEP> 44-46"C <tb> <SEP> CH3 <tb> <SEP> 6 <SEP> -CH,-CH- <SEP> nD <SEP> nO <SEP> 1.5325 <tb> <SEP> tH, <tb> <SEP> 7 <SEP> CH2CE <SEP> HOC2Hs <SEP> nEO <SEP> 1.5126 <tb> <SEP> 8 <SEP> -CH-CH2-O-C2H5 <SEP> nD <SEP> 1.5234 <tb> <SEP> CH3 <tb> <SEP> 9 <SEP> -CH-CH-O-CH3 <SEP> Kp. <SEP> 113-115"/0,01 <SEP> Torr <tb> <SEP> II <tb> <SEP> CH3 <SEP> CH3 <tb> 10 <SEP> CH <SEP> - <SEP> CH2 <SEP> - <SEP> O <SEP> -CH3 <SEP> Kp. <SEP> 120-122 /0,03 <SEP> Torr <tb> <SEP> C2H5 <tb> Einige der entsprechenden Ausgangstoffe der Formel II oder ihre Vorprodukte sind nachstenend aufgeführt: N-(2'-Allyloxyäthyl)-2,6-xylidin . . Kp. 83-87 C/0,2 Torr N-(2'-Cyclopropoxyäthyl)-2,6-xylidin . Kp. 79-80 C/0,15 Torr N-(2'-Cyclopropylmethyloxyäthyl)-2,6-xylidin .. <SEP> 44-46 "C <tb> <SEP> CH3 <tb> <SEP> 6 <SEP> -CH, -CH- <SEP> nD <SEP> nO <SEP> 1.5325 <tb> <SEP> tH, <tb> <SEP> 7 <SEP> CH2CE <SEP> HOC2Hs <SEP> nEO <SEP> 1.5126 <tb> <SEP> 8 <SEP> -CH-CH2-O-C2H5 <SEP> nD <SEP> 1.5234 <tb> <SEP> CH3 <tb> <SEP> 9 <SEP> -CH-CH-O-CH3 <SEP> Kp. <SEP> 113-115 "/ 0.01 <SEP> Torr <tb> <SEP> II <tb> <SEP> CH3 <SEP> CH3 <tb> 10 <SEP> CH <SEP> - <SEP> CH2 <SEP> - <SEP> O <SEP> -CH3 <SEP> Kp. <SEP> 120-122 / 0.03 <SEP> Torr <tb> <SEP> C2H5 <tb> Some of the corresponding starting materials of the formula II or their precursors are listed below: N- (2'-allyloxyethyl) -2,6-xylidine. . Bp 83-87 C / 0.2 Torr N- (2'-Cyclopropoxyethyl) -2,6-xylidine. Bp. 79-80 C / 0.15 Torr N- (2'-Cyclopropylmethyloxyäthyl) -2,6-xylidine .. Kp. 96-101 C/0,15 Torr N-(2'-Methoxy-2'-methyläthyl)-2,6-xylidin . Kp. 54-57 C/0,04 Torr N-(2'Methoxy-1'-methyläthyl)-2,6-xylidin ... Kp. 54-57 C/0,04 Torr N-(2'-Hydroxypropyl)-2,6-xylidin ............ . Kp. 81-83 C/0,1 Torr N-(2'-Hydroxypropyl)-N-chloroacetyl-2,6-xylidin .. Smp. 83-85 C N-(2'-Äthoxy-1'-methyläthyl)-2,6-xylidin .. . . Kp. 142-145 C/17 Torr N-(2'-Methoxy-1'-äthyläthyl)-2,6-xylidin ..... . Kp.143-144 C/16 Torr N-(2'-Methoxy-1',2'-dimethyläthyl)-2,6-xylidin . Bp 96-101 C / 0.15 Torr N- (2'-methoxy-2'-methylethyl) -2,6-xylidine. Bp 54-57 C / 0.04 torr N- (2'-methoxy-1'-methylethyl) -2,6-xylidine ... Bp 54-57 C / 0.04 torr N- (2'-hydroxypropyl ) -2,6-xylidine ............. Bp. 81-83 C / 0.1 Torr N- (2'-hydroxypropyl) -N-chloroacetyl-2,6-xylidine .. Mp. 83-85 C N- (2'-ethoxy-1'-methylethyl) -2,6-xylidine ... . Bp 142-145 C / 17 Torr N- (2'-methoxy-1'-ethylethyl) -2,6-xylidine ...... Bp 143-144 C / 16 torr N- (2'-methoxy-1 ', 2'-dimethylethyl) -2,6-xylidine. . Kp. 124-126 C/8 Torr Glieder der Alkylenkette sind und R einen Alkenylrest mit 3 oder 4 Kohlenstoffatomen, den Cyclopropylrest, den Cyclopropylmethylrest oder, falls A einen verzweigten Alkylenrest bedeutet, auch einen Alkylrest mit 1 bis 3 Kohlenstoffatomen darstellt, dadurch gekennzeichnet, dass man ein substituiertes Anilin der Formel II EMI3.1 worin A und R die für Formel I genannte Bedeutung haben, mit einem Chloracetyliernngsmittel acyliert. . Bp. 124-126 C / 8 Torr members of the alkylene chain and R is an alkenyl radical with 3 or 4 carbon atoms, the cyclopropyl radical, the cyclopropylmethyl radical or, if A is a branched alkylene radical, also an alkyl radical with 1 to 3 carbon atoms, characterized in that that a substituted aniline of the formula II EMI3.1 in which A and R have the meaning given for formula I, acylated with a chloroacetylating agent. UNTERANSPRÜCHE 1. Verfahren gemäss Patentanspruch, wobei in Anwesenheit eines gegenüber den Reaktionspartnern inerten Lösungs- oder Verdünnungsmittels gearbeitet wird. SUBCLAIMS 1. The method according to claim, wherein the reaction is carried out in the presence of a solvent or diluent which is inert towards the reactants. 2. Verfahren gemäss Patentanspruch oder Unteranspruch 1, wobei als Chloracetylierungsmittel das Anhydrid oder ein Halogenid der Chloressigsäure verwendet wird. 2. The method according to claim or dependent claim 1, the anhydride or a halide of chloroacetic acid being used as the chloroacetylating agent. 3. Verfahren gemäss Patentanspruch oder Unteranspruch 1, wobei als Chloracetyliernngsmittel Chloressigsäureester verwendet wird. 3. The method according to claim or dependent claim 1, wherein chloroacetic acid ester is used as the chloroacetylating agent. 4. Verfahren gemäss Patentanspruch oder Unteranspruch 1, wobei die Acylierung in Gegenwart eines säurebindenden Mittels durchgeführt wird. 4. The method according to claim or dependent claim 1, wherein the acylation is carried out in the presence of an acid-binding agent. 5. Verfahren gemäss Patentanspruch oder Unteranspruch 1, wobei die Verbindung N-(l '-Methoxyprop-2'-yl)-N-chloracetyl-2,6- EMI3.2 <tb> dimethylanilin <SEP> der <SEP> Formel <tb> <SEP> C,H3 <SEP> CH-CH2 <SEP> -O <SEP> -CH <tb> <SEP> J <SEP> CH-CK2-O-CH3 <tb> <SEP> CH3 <tb> <SEP> 3 <tb> hergestellt wird. 5. The method according to claim or dependent claim 1, wherein the compound N- (l'-methoxyprop-2'-yl) -N-chloroacetyl-2,6- EMI3.2 <tb> dimethylaniline <SEP> of the <SEP> formula <tb> <SEP> C, H3 <SEP> CH-CH2 <SEP> -O <SEP> -CH <tb> <SEP> J <SEP> CH-CK2-O-CH3 <tb> <SEP> CH3 <tb> <SEP> 3 <tb> is produced. 6. Verfahren gemäss Patentanspruch oder Unteranspruch 1, wobei die Verbindung N-(2'-Methoxypropyl)-N-chloracetyl-2,6dimethylanilin der Formel EMI3.3 hergestellt wird. 6. The method according to claim or dependent claim 1, wherein the compound N- (2'-methoxypropyl) -N-chloroacetyl-2,6dimethylaniline of the formula EMI3.3 will be produced.
CH728372A 1972-02-07 1972-05-16 Haloacetanilides - selective herbicides CH576945A5 (en)

Priority Applications (42)

Application Number Priority Date Filing Date Title
BE795021D BE795021A (en) 1972-02-07 HALOGENO-ACETANILIDES TO INFLUENCE PLANT GROWTH
CH728372A CH576945A5 (en) 1972-05-16 1972-05-16 Haloacetanilides - selective herbicides
SE7301032A SE400775B (en) 1972-02-07 1973-01-25 N-SUBSTITUTED 2,6-DIMETHYL-CHLOROACETANILIDES WITH GROWTH REGULATORY EFFECTS AND HERBICID EFFECTS, SPECIFICALLY USED AS SELECTIVE HERBICID
IL41414A IL41414A (en) 1972-02-07 1973-01-29 N-substituted chloroacetanilides,their manufacture and compositions for regulating plant growth containing them
CA162,480A CA1047532A (en) 1972-02-07 1973-01-31 Haloacetanilides for regulating plant growth
SU7301882613A SU581836A3 (en) 1972-02-07 1973-01-31 Herbicide
NL7301481.A NL161133B (en) 1972-02-07 1973-02-01 PROCEDURE FOR PREPARATION OF PREPARATIONS FOR INFLUENCING PLANT GROWTH BASED ON N-ALKOXYALKYL-2,6-DIALKYLCHLOROACETANILIDES, PROCEDURE FOR SELECTIVE CONTROL OF UNDESIRABLE PLANTS- GROWING PLANTS-WAKE-ALKYLY-PREVIOUS-PREVIOUSLY-PREVIOUS-PREVIOUS CULTURE 2,6-DIALKYLCHLOROACEETANILIDES.
AU51675/73A AU470433B2 (en) 1972-02-07 1973-02-01 Haloacetanilides for regulating plant growth
BG022621A BG20534A3 (en) 1972-02-07 1973-02-05 HERBICIDE
DE19732305495 DE2305495C3 (en) 1972-02-07 1973-02-05 N-substituted chloroacet anilide, process for their preparation and means for influencing plant growth
DD168667A DD103122A5 (en) 1972-02-07 1973-02-05
YU290/73A YU39295B (en) 1972-02-07 1973-02-05 Process for preparing substituted chloroacetylanilides
RO73102519A RO80063A (en) 1972-02-07 1973-02-05 PROCESS FOR THE PREPARATION OF N-SUBSTITUTED CHLORACETANILIDES
JP1512273A JPS5614083B2 (en) 1972-02-07 1973-02-06
GB574073A GB1422473A (en) 1972-02-07 1973-02-06 Chloroacetanilides for regulating plant growth
OA54825A OA04526A (en) 1972-02-07 1973-02-06 Halogenoacetanilides to influence plant growth.
AT102373A AT321639B (en) 1972-02-07 1973-02-06 Preparations for influencing plant growth
PL1973179610A PL93822B1 (en) 1972-02-07 1973-02-06 2-Chloro-N-(2'-methoxypropyl)- and 2-chloro-N-(2'-ethoxypropyl)-2'',6''-dimethyl-acetanilide as long term weed killers[US4412855A]
ES411328A ES411328A1 (en) 1972-02-07 1973-02-06 2-Chloro-N-(2'-methoxypropyl)- and 2-chloro-N-(2'-ethoxypropyl)-2'',6''-dimethyl-acetanilide as long term weed killers
HUCI1337A HU165898B (en) 1972-02-07 1973-02-06
IT20087/73A IT983445B (en) 1972-02-07 1973-02-06 CHLORINE ACETANILIDES TO INFLUENCE THE GROWTH OF PLANTS
PH14315A PH10362A (en) 1972-02-07 1973-02-06 Haloacetanilides for regulating plant growth
EG48/73A EG10663A (en) 1972-02-07 1973-02-06 Haloacetanilides for regulating plant growth
PL1973160616A PL89203B1 (en) 1972-02-07 1973-02-06 2-Chloro-N-(2'-methoxypropyl)- and 2-chloro-N-(2'-ethoxypropyl)-2'',6''-dimethyl-acetanilide as long term weed killers[US4412855A]
DK62273AA DK140531B (en) 1972-02-07 1973-02-06 N-substituted chloroacetanilides for use as plant growth regulators and herbicides.
FR7304098A FR2171171B1 (en) 1972-02-07 1973-02-06
TR17988A TR17988A (en) 1972-02-07 1973-02-07 PROCEDURES FOR OBTAINING NEW BRACELETS PROCEDURES FOR OBTAINING NEW BRACELETS
CS906A CS168627B2 (en) 1972-02-07 1973-02-07
IN1037/CAL/73A IN138952B (en) 1972-02-07 1973-05-03
AR248005A AR231052A1 (en) 1972-05-16 1973-05-14 HERBICIDE COMPOSITIONS BASED ON DERIVATIVES OF ESTERIFIED N-HYDROXIALKYL-N-CHLORACETIL-2,6-DIMETHYLLANILINE AND PROCEDURE FOR THE PREPARATION OF SUCH DERIVATIVES
BR3548/73A BR7303548D0 (en) 1972-05-16 1973-05-15 PROCESS OF PREPARATION OF N-SUBSTITUTED HALOACETANILIDES TO COMPOSITES BASED ON THE SAME FOR REGULATING PLANT GROWTH AND A PROCESS TO COMBAT, SELECTIVELY, WEED PLANTS IN CULTIVATED PLANT FIELDS
CU33904A CU33904A (en) 1972-05-16 1973-05-15 NEW SUBSTITUTED HALOGENACETANILIDES COMPOUNDS
AT328274A AT338249B (en) 1972-02-07 1974-04-19 PROCESS FOR PREPARING NEW SUBSTITUTED CHLOROACETANILIDES
US05/548,042 US3952056A (en) 1972-02-07 1975-02-07 Plant growth regulating agent
SU7502163132A SU580831A3 (en) 1972-05-16 1975-08-14 Method of preparing chloracetylized 2,6-xylidines
US05/653,556 US4019894A (en) 1972-02-07 1976-01-29 Plant growth regulating agent
DK201976A DK201976A (en) 1972-02-07 1976-05-05 PROCEDURE FOR SELECTIVE CONTROL OF UNDESIRABLE PLANT GROWTH
DK201776A DK142161B (en) 1972-02-07 1976-05-05 Method for selectively controlling undesired plant growth in crop plants and means for practicing this method.
US05/688,868 US4283221A (en) 1972-02-07 1976-05-21 Plant growth regulating agent
JP52114515A JPS5835502B2 (en) 1972-02-07 1977-09-22 Method for producing substituted chloroacetanilide derivative
US05/905,835 US4160660A (en) 1972-02-07 1978-05-15 Acetanilide plant growth regulating agent
US05/944,816 US4412855A (en) 1972-02-07 1978-09-22 2-Chloro-N-(2'-methoxypropyl)- and 2-chloro-N-(2'-ethoxypropyl)-2",6"-dimethyl-acetanilide as long term weed killers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH728372A CH576945A5 (en) 1972-05-16 1972-05-16 Haloacetanilides - selective herbicides

Publications (1)

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CH576945A5 true CH576945A5 (en) 1976-06-30

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CH728372A CH576945A5 (en) 1972-02-07 1972-05-16 Haloacetanilides - selective herbicides

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AR (1) AR231052A1 (en)
BR (1) BR7303548D0 (en)
CH (1) CH576945A5 (en)
CU (1) CU33904A (en)
SU (1) SU580831A3 (en)

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CU33904A (en) 1983-10-04
SU580831A3 (en) 1977-11-15
AR231052A1 (en) 1984-09-28
BR7303548D0 (en) 1974-07-11
CU21028L (en) 1979-01-16

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