CH606029A5 - N-Furoyl-N-aryl-alanine esters - Google Patents

N-Furoyl-N-aryl-alanine esters

Info

Publication number
CH606029A5
CH606029A5 CH1506177A CH1506177A CH606029A5 CH 606029 A5 CH606029 A5 CH 606029A5 CH 1506177 A CH1506177 A CH 1506177A CH 1506177 A CH1506177 A CH 1506177A CH 606029 A5 CH606029 A5 CH 606029A5
Authority
CH
Switzerland
Prior art keywords
sep
formula
cooch3
active ingredient
smp
Prior art date
Application number
CH1506177A
Other languages
German (de)
Inventor
Adolf Dr Hubele
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 claimed from CH457274A external-priority patent/CH590608A5/en
Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag
Priority to CH1506177A priority Critical patent/CH606029A5/en
Priority claimed from CH159175A external-priority patent/CH603041A5/en
Publication of CH606029A5 publication Critical patent/CH606029A5/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/30—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D327/06—Six-membered rings
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Wood Science & Technology (AREA)
  • Zoology (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

N-Furoyl-N-aryl-alanine esters prepd. e.g. by reacting N-aryl-alanine esters with 2-furoic acid or its derivs.

Description

  

  
 



   Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von neuen Aniliden, welche der Formel I entsprechen
EMI1.1     
 .worin   Rl      C1-C4-Alkyl,      Cl-C4-Alkoxy    oder Halogen, R2 Was serstoff,   C1-C3-Alkyl    oder Halogen, R5 Wasserstoff,   Cl-C3-Al-    kyl oder Halogen, R6 Wasserstoff oder Methyl sind, wobei die Gesamtzahl von C-Atomen der Substituenten R1, R2, R5 und R6 im Phenylring die Zahl 8 nicht übersteigt,
EMI1.2     
 darstellen, wobei R', R" und R"' unabhängig voneinander Wasserstoff, Methyl oder Äthyl bedeuten und R4 einen gegebenenfalls durch Methyl und/oder Halogen substituierten 5oder 6-gliedrigen heterocyclischen Rest mit 1 oder 2 Heteroatomen bedeutet.



   Unter Alkyl und als   Alkyl:l ell    einer Alkoxy-Gruppe   smd    je nach Zahl der angegebenen Kohlenstoffatome folgende Gruppen zu verstehen: Methyl, Äthyl, n-Propyl, iso-Propyl oder n-, iso-, sec- oder tert-Butyl. Als Halogen kommen Fluor, Chlor, Brom oder Jod in Frage.



   Als 5- bis 6gliedriger heterocyclischer Rest können z. B.



  genannt werden: Furan, Thiophen, Pyridin, Pyrimidin, 2,3-Dihydro-4H-pyran,   1 ,4-Oxathi-(2 > in,    Tetrahydrofuran, Morpholin oder Piperidin, welche gegebenenfalls durch Methyl undloder Halogen substituiert sein können.



   Die Herstellung der Verbindungen der Formel I erfolgt erfindungsgemäss so, dass das entsprechende Acylanilid der Formel II
EMI1.3     
 mit Butyl-Lithium, Na-Hydrid oder K2CO3 in Pyridin oder Tetrahydrofuran in das Alkalisalz überführt wird, welches dann mit dem Halogenessigsäure-Ester oder -Amid bzw. dem a-Ha logenpropionsäure-Ester oder -Amid der Formel III
Hal-X-R3 (III) weiter umgesetzt wird.



   In den Formeln II und III haben   Rl    bis R6 und X die für
Formel I gegebenen Bedeutungen, während Hal für ein Halo genatom, vorzugsweise Chlor oder Brom steht.



   Die Umsetzungen können auch in An- oder Abwesenheit von weiteren gegenüber den Reaktionsteilnehmern inerten
Lösungs- oder Verdünnungsmitteln durchgeführt werden. Es kommen beispielsweise folgende in Frage: Aliphatische oder aromatische Kohlenwasserstoffe wie Benzol, Toluol, Xylole,
Petroläther, Äther und ätherartige Verbindungen wie Dialky läther oder Dioxan, oder auch Nitrile wie Acetonitril; und
Gemische solcher Lösungsmittel untereinander.



   Die Reaktionstemperaturen liegen zwischen -20   "C    und
180   "C,    vorzugsweise zwischen   0     und 120   "C.   



   Die Verbindungen der Formel I besitzen die Eigenschaft, das Wachstum und den Gesundheitszustand von Nutztieren und das Wachstum und die Entwicklung von Nutzpflanzen sowie den Nutzpflanzenanbau, z. B. durch selektive Unkraut bekämpfung oder durch Wuchsregulation, günstig zu beeinflussen. Unter anderem eignen sie sich zur Bekämpfung ver schiedenartiger pflanzlicher und tierischer Schädlinge.



   Überragende Wirkung aber erzielen die Verbindungen der Formel I als Pflanzenfungizide. Sie werden mit üblichen Trägerstoffen zu entsprechenden Mitteln formuliert. Die Verbindungen der Formel I, worin X -CH(CH3)- bedeutet, besitzen ein asymmetrisches Kohlenstoffatom und können auf übliche Art in optische Antipoden gespalten werden. Hierbei besitzt die enantiomere D-Form die stärkere pflanzenfungi zide Wirkung.



   Das nachfolgende Beispiel dient zur näheren Erläuterung der Erfindung, ohne dieselbe einzuschränken. Die Temperatur angaben im Beispiel und in den folgenden Tabellen bezie hen sich auf Celsiusgrade.



   Beispiel
Man stellt aus 2,4 g (0,055 Mole)   55 /0iger      Natriumhydrid     Öldispersion und 25 ml Tetrahydrofuran eine Suspension her. Zu dieser tropft man bei Raumtemperatur 10,75 g (0,05
Mole) in 125 ml Tetrahydrofuran gelöstes Furan-2-carbonsäu    re-2',6'-dimethylanilid,    Smp.   125-128 ,    das man durch Reaktion von 2,6-Dimethylanilin mit z. B. 2-Furanoylchlorid gewonnen hat. Das Reaktionsgemisch wird danach 30 Min. bei normaler Temperatur und weitere 30 Min. bei 45   "C    gerührt.



  Nach dem Abkühlen werden bei Raumtemperatur 9,2 g (0,055 Mole) 2-Brompropionsäuremethylester in 10 ml Tetrahydrofuran gelöst zugetropft. Dann wird 1 Std. bei normaler Temperatur gerührt und 24 Std. unter Rückfluss erhitzt.



  Nach dem Abkühlen wird filtriert und das Filtrat am Rotationsverdampfer eingeengt. Das als Rückstand verbleibende   N-(1¯Methoxycarbonyl-äthyl)-N-(furan-(2' -carbonyl2,6-dimet-    hylanilin wird aus Äther/Petroläther umkristallisiert; Smp.



  82-84   "C.     



  Analog lassen sich folgende Verbindungen herstellen:
EMI2.1     

EMI2.2     


<tb> VeLb. <SEP> R, <SEP> R2 <SEP> -X'R3 <SEP> Physikal.
<tb>



   <SEP> r <SEP> Konstante
<tb>  <SEP> ¯¯ <SEP> . <SEP> 
<tb> 1 <SEP> CH, <SEP> 6-H <SEP> -CH-COOCH3 <SEP> Smp. <SEP> 85-870
<tb> 2 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CH-COOCH3 <SEP> Sdp. <SEP> 162-163 /
<tb>  <SEP> cH3 <SEP> 0,1 <SEP> Torr
<tb> 3 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-COO-C2H5 <SEP> Smp. <SEP> 90-940
<tb>  <SEP> CH3
<tb> 4 <SEP> CH3 <SEP> H <SEP> -CH <SEP> -COOCH. <SEP> Sdp. <SEP> 126-148 /
<tb>  <SEP> CH3 <SEP> 0,02 <SEP> Torr
<tb> 5 <SEP> CH3 <SEP> 3-CH3 <SEP> -CH-COOCH3 <SEP> Sdp.151 /0,03Torr
<tb>  <SEP> CH3
<tb> 6 <SEP> CH3 <SEP> 4-CH3 <SEP> -0H-COOCH3 <SEP> Smp. <SEP> 89-91 
<tb>  <SEP> cH3
<tb> 7 <SEP> CH3 <SEP> 5-CH3 <SEP> -CH-COOCH3 <SEP> Smp.

  <SEP> 114-116 
<tb>  <SEP> CH3
<tb>  <SEP> CD) <SEP> -F'orm
<tb> 8 <SEP> CR3 <SEP> 6-cH3 <SEP> cH?C00CH3 <SEP> SmO2 <SEP> 1030
<tb>  <SEP> 3 <SEP> 3 <SEP> bH3 <SEP> [ 1g " <SEP> -47,0+0,7 ;
<tb>  <SEP> c-1,73% <SEP> g/v <SEP> in
<tb>  <SEP> Aceton
<tb> 9 <SEP> CH3 <SEP> 6-C2H5 <SEP> -ÇH2-COOCH3 <SEP> Smp. <SEP> 91-94 
<tb> 10 <SEP> CR3 <SEP> 6-Cl <SEP> -CR-COOC <SEP> Smp.
<tb>



   <SEP> H3 <SEP> 2 <SEP> 5 <SEP> Smp. <SEP> 112-113
<tb>   
EMI3.1     


<tb> Verb. <SEP> R1 <SEP> R2 <SEP> wX-R3 <SEP> IConstante
<tb>  <SEP> 11 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-CO-NH, <SEP> Smp.128-130 
<tb>  <SEP> 12 <SEP> C1 <SEP> 5-C1 <SEP> -CH-COOCH3 <SEP> Smp.11O-1120
<tb>  <SEP> CR3
<tb>  <SEP> 13 <SEP> C2H5 <SEP> 6-C2H5 <SEP> -CH2-CO-NH2 <SEP> Smp.127-1280
<tb>  <SEP> 14 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOCH3 <SEP> Smp. <SEP> 92
<tb>  <SEP> CR3
<tb>  <SEP> 15 <SEP> nC4H9-O- <SEP> H <SEP> -ICH-COOCH3 <SEP> Sdp.170-173 /
<tb>  <SEP> CH3 <SEP> 0,04 <SEP> Torr
<tb>  <SEP> 16 <SEP> CH3 <SEP> 6CH3 <SEP> -CH;CO-NHCH3 <SEP> Smp. <SEP> 141-143 
<tb>  <SEP> CR
<tb>  <SEP> 3
<tb>  <SEP> 17 <SEP> iso-C3H7 <SEP> 6-isoC3H7 <SEP> -CH-COOCH <SEP> Smp. 

  <SEP> 86-960
<tb>  <SEP> 18 <SEP> iso-C3H7 <SEP> H <SEP> -CH-COOCH3 <SEP> Sdp.1580/O,O3Torr
<tb>  <SEP> OH3
<tb>  <SEP> 19 <SEP> F <SEP> H <SEP> -CH-COOCH3 <SEP> Sdp.l500/0,03Torr
<tb>  <SEP> OH3
<tb>  <SEP> 20 <SEP> C1 <SEP> H <SEP> 0111 <SEP> ;COOCH3 <SEP> Sdp.1550/O,O5Torr
<tb>  <SEP> CR3
<tb>  <SEP> 21 <SEP> C1 <SEP> 6-C1 <SEP> 'CH-COOCH3 <SEP> Smp.113-1160
<tb>  <SEP> CR3
<tb>   
EMI4.1     


<tb>  <SEP> Verb <SEP> . <SEP> R <SEP> R <SEP> PhysLkal.
<tb>



   <SEP> 1 <SEP> 2 <SEP> -X-R3 <SEP> Konstante
<tb> 22 <SEP> J <SEP> H <SEP> -CH-COOCH3 <SEP> Sdp.145 <SEP> /0,2Torr
<tb>  <SEP> 1 <SEP> 3
<tb> 2-3 <SEP> Br <SEP> H <SEP> -H-COOCH3 <SEP> Sdp.1450/0,05Torr
<tb>  <SEP> CH3
<tb> 24 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-COOCH3 <SEP> Smp. <SEP> 98-990
<tb> 25 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-C0-NHCH3 <SEP> Smp.164-1650
<tb> 26 <SEP> CH3 <SEP> 6-OH3 <SEP> -CH2-CO-N(CH3) >  <SEP> Smp.142-1450
<tb> 27 <SEP> cd <SEP> 4-CH30- <SEP> -011-000CH3 <SEP> ; <SEP> Sdp <SEP> 168 Sdp.1680
<tb>  <SEP> OH3 <SEP> 4-CH,O- <SEP> /0,07Torr
<tb> 28 <SEP> CH3 <SEP> W-sec.C4H90 <SEP> -CH-COOCH3 <SEP> Sdp.l780 <SEP> /
<tb>  <SEP> O,OSTorr.
<tb>



  29 <SEP> 02H5 <SEP> 6-C2H5 <SEP> -CH2-C0-CHi2 <SEP> zu2 <SEP> Smp.178-181 
<tb> 30 <SEP> 02H5 <SEP> 6-C2H5 <SEP> -CH2-COOCH3 <SEP> Smp. <SEP> 880
<tb> 31 <SEP> 02H5 <SEP> 6-C2H5 <SEP> -CH2-C0-NHC2H5 <SEP> Smp. <SEP> 158-159 
<tb>    Ferner auch Verbindungen der Formel
EMI5.1     

EMI5.2     


<tb> Verb. <SEP> R <SEP> R2 <SEP> -X-R3 <SEP> Physikal.
<tb>



   <SEP> 1
<tb>  <SEP> I <SEP> KonstanLe
<tb> 33 <SEP> CH3 <SEP> 6-CH3 <SEP> -CR-000CR3 <SEP> (D) <SEP> -Form
<tb>  <SEP> Smp. <SEP> 91.920
<tb>  <SEP> CH3 <SEP> Smp <SEP> 91-92 
<tb>  <SEP> D <SEP> a <SEP> zu+0,80;
<tb>  <SEP> c=1,52% <SEP> g/v <SEP> in
<tb>  <SEP> Aceton
<tb> 34 <SEP> CH3 <SEP> 6cH3 <SEP> -CH2'co <SEP> -N <SEP> (CH <SEP> Oel
<tb> 35 <SEP> C2H5 <SEP> 6-C2H5 <SEP> -CH2-C0-NH2 <SEP> Smp.144-1450
<tb>  <SEP> 36 <SEP> CH3 <SEP> 6-C1 <SEP> -H-COO-C2H5 <SEP> Oel
<tb>  <SEP> 3
<tb>  <SEP> 37 <SEP> CH3 <SEP> li-sec.C,H <SEP> -O- <SEP> -yH-COOCH3 <SEP> Sdp.1850/0,O6Torr
<tb>  <SEP> 3
<tb>  <SEP> 38 <SEP> F <SEP> H <SEP> -C1H-COOCH3 <SEP> Sdp.1620/O,lTorr
<tb>  <SEP> 3
<tb>  <SEP> 39 <SEP> C1 <SEP> H <SEP> -IH-COOCH3 <SEP> Sdp.1600/0,lTorr
<tb>  <SEP> CH3
<tb>  <SEP> 40 <SEP> J <SEP> H <SEP> -fH-COOCH3 <SEP> Sdp.168-172 /
<tb>  <SEP> CH3 <SEP> ),1 <SEP> Torr
<tb>  <SEP> 41 <SEP> 

   CH3 <SEP> 4-CH3 <SEP> -CH-COOCH3
<tb>  <SEP> 3 <SEP> ),2 <SEP> Torr
<tb>  <SEP> 3 <SEP> 2 <SEP> Torr
<tb>  <SEP> 42 <SEP> CH3 <SEP> 6-C1 <SEP> -7H-COOCH3 <SEP> Smp. <SEP> 80-87 
<tb>  <SEP> OH3
<tb>    Ferner die Verbindungen der allgemeinen Formel:
EMI6.1     

EMI6.2     


<tb> Verb. <SEP> R <SEP> R2 <SEP> -X-R3 <SEP> R4 <SEP> 1 <SEP> .Phys <SEP> ika <SEP> 1.
<tb>



   <SEP> 1 <SEP> Konstanre
<tb>  <SEP> 43 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-COOCH3 <SEP> t <SEP> Smp.95-96 
<tb>  <SEP> 44 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOCH3 <SEP> 4 <SEP> Smp.85-87 
<tb>  <SEP> 45 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOC2H5 <SEP> t <SEP> Smp. <SEP> 63-66 
<tb>  <SEP> 0113
<tb>  <SEP> 46 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CH2-COOCH3 <SEP> t <SEP> Smp. <SEP> 88-90 
<tb>  <SEP> 47 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-CON(CH3)2 <SEP> t <SEP> Smp. <SEP> 148-152 
<tb>  <SEP> 48 <SEP> CH3 <SEP> 6-CH3 <SEP> -OH-OOOCH3 <SEP> Smp.100-107 
<tb>  <SEP> OH3 <SEP> H3C0
<tb>  <SEP> 49 <SEP> CH3 <SEP> 6 <SEP> -02H5 <SEP> -CH2-COOCH3 <SEP> X <SEP> n25 <SEP> e <SEP> 1,5276
<tb>  <SEP> 50 <SEP> 01130 <SEP> 6-C1 <SEP> -CH;COOCH3 <SEP> S <SEP> n <SEP> Smp. <SEP> 98 <SEP> - <SEP> 100 
<tb>  <SEP> 0113
<tb>   
EMI7.1     


<tb> Verb. <SEP> R1 <SEP> R2 <SEP> -X-R3 <SEP> R4 <SEP> Physikal.
<tb>



   <SEP> Konstante
<tb> 51 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-COOCH3 <SEP> 3¸ <SEP> Smp. <SEP> 50.510
<tb> 52 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-COOCH3 <SEP> -71mp.97-980
<tb>  <SEP> CR3
<tb> 53 <SEP> H3 <SEP> 6-1 <SEP> -CH-COOCH3 <SEP> Smp.73-85o
<tb>  <SEP> OH3
<tb> 54 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CH2-COOCII3 <SEP> Däl <SEP> Smp.76-770
<tb>  <SEP> 0
<tb> 55 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOCH3 <SEP> X <SEP> O <SEP> J <SEP> Smp.108-110 
<tb>  <SEP> 3 <SEP> 0
<tb> 56 <SEP> H3 <SEP> 6-CH3 <SEP> -C1-COOCH3 <SEP> XJ <SEP> Smp. <SEP> 138 
<tb>  <SEP> OH3 <SEP> -CH-COOCH <SEP> 0
<tb>  <SEP> 20
<tb> 57 <SEP> isoC3H7 <SEP> 6-isoC3H7 <SEP> -CH-COOCH3 <SEP> JW <SEP> O <SEP> ; <SEP> CH3 <SEP> nD  <SEP> 1.6900
<tb>  <SEP> C1H3 <SEP> 0 <SEP> CH3
<tb> 58 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOCH3 <SEP> X <SEP> Css <SEP> Smp.120-122
<tb> 59 <SEP> H3 <SEP> 6-CH3 <SEP> -CH-COOCH3 <SEP> z <SEP> 8 <SEP> Smp.

  <SEP> 91-930
<tb>  <SEP> 3 <SEP> 00113
<tb>  <SEP> CH3 <SEP> 00113
<tb>   
EMI8.1     


<tb> Verb. <SEP> h <SEP> R2 <SEP> -X-R3 <SEP> R4 <SEP> PhysLkal
<tb>  <SEP> 60 <SEP> CH3 <SEP> 6-C1 <SEP> -F""""" <SEP>  > ) <SEP> smp. <SEP> 11
<tb>  <SEP> OH3
<tb>  <SEP> 61 <SEP> CH3 <SEP> 6-C1 <SEP> ; <SEP> ICH-COOCH3 <SEP> oD;) <SEP> X <SEP> 9 <SEP> Smp.118-1190
<tb>  <SEP> 62 <SEP> CH3 <SEP> 6-C1 <SEP> -tH-COOC2H5 <SEP> C <SEP> X3 <SEP> Smp. <SEP> 1260
<tb>  <SEP> 63 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOCK, <SEP> 4 <SEP> Stnp.150-1510
<tb> 64 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-COOCH3 <SEP> CH- <SEP> ° <SEP> O <SEP> 3 <SEP> Smp. <SEP> 81-830
<tb> 65 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CY-COOCH, <SEP> Sdp.

  <SEP> Sdp.190-2100
<tb>  <SEP> Olis <SEP> /0,5 <SEP> Torr
<tb> 66 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CH2-COOCH3 <SEP> zu <SEP> ) <SEP> Sdp.190-195 
<tb>  <SEP> CR30 <SEP> /0,2 <SEP> /0,2 <SEP> /0,2 <SEP> Torr
<tb> 67 <SEP> CH3 <SEP> 6-CH3 <SEP> - <SEP> -CH2-COOCH3 <SEP> 7 <SEP> Smp. <SEP> 75o
<tb> 68 <SEP> CH3 <SEP> 6-CH3 <SEP> -8H-COOCH3 <SEP> rO <SEP> g <SEP> Smp. <SEP> 83-85 
<tb>  <SEP> OH3
<tb>   
EMI9.1     


<tb>  <SEP> Physikal.
<tb>



  Verb. <SEP> RL <SEP> R2 <SEP> -X-R3 <SEP> R4 <SEP> Konstante
<tb>  <SEP> 69 <SEP> CH3 <SEP> 6-C1 <SEP> -iH-COOCH3 <SEP> es <SEP> Smp. <SEP> 90-1050
<tb>  <SEP> 0113 <SEP> 11
<tb>  <SEP> 70 <SEP> C1 <SEP> I <SEP> 6-C1 <SEP> -CH-COOCH <SEP> Oel
<tb>  <SEP> OH3 <SEP> 0
<tb>  <SEP> 71 <SEP> CH3-0- <SEP> H <SEP> -CH2-CONH2 <SEP> S <SEP> Oel
<tb>  <SEP> 72 <SEP> CH3 <SEP> 4-C1 <SEP> CH3 <SEP> n <SEP> Oel
<tb>  <SEP> 0113
<tb>  <SEP> 73 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-COOCH <SEP> CH; <SEP> CH <SEP> X <SEP> CH3 <SEP> Smp.91-93 
<tb>  <SEP> 74 <SEP> C1 <SEP> 5-C1 <SEP> -ICH-COOCH3 <SEP> | <SEP> Oel
<tb>  <SEP> iacx
<tb>  <SEP> 75 <SEP> Cl <SEP> 5-C1 <SEP> -CH-COOCH3 <SEP> CH3 <SEP> t <SEP> Oel
<tb>  <SEP> LH3 <SEP> OH
<tb>  <SEP> 76 <SEP> CH3 <SEP> 6-CH3 <SEP> -H-COOCH3 <SEP> X <SEP> Smp.

  <SEP> 99-100"
<tb>  <SEP> CH3 <SEP> Ho
<tb>  <SEP> 77 <SEP> CH3 <SEP> 6-CH3 <SEP> -CR-C0OCR <SEP> X <SEP> O <SEP> 3 <SEP> Stnp. <SEP> 1300
<tb>  <SEP> 3
<tb>  <SEP> OH3 <SEP> 011o
<tb>  <SEP> 78 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-CO-NH <SEP> Smp. <SEP> 85-88 
<tb>  <SEP> O2H5 <SEP> 3o
<tb>    Ferner die Verbindungen der allgemeinen Formel Ia
EMI10.1     

EMI10.2     


<tb>  <SEP> IFhysLkal.
<tb>

 

  79 <SEP> | <SEP> CH3 <SEP> CH3 <SEP> 1 <SEP> H <SEP> JHH3CO <SEP> 3 <SEP> JÜ
<tb> 80 <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> 5CH3 <SEP> -CH-COOCH3 <SEP> Smp. <SEP> 83,5
<tb>  <SEP> 113 <SEP> 850
<tb> 81 <SEP> CH3 <SEP> CH3 <SEP> 02115 <SEP> H <SEP> -cClH;COOCH3 <SEP> 2C <SEP> Smp12o66
<tb> 82 <SEP> C2H5 <SEP> CH3 <SEP> CH3 <SEP> lI <SEP> -2H-COOCH3 <SEP> U <SEP> Sdp. <SEP> l76
<tb>  <SEP> H3 <SEP> O <SEP> 177 /0,05Torr
<tb> 83 <SEP> CH3 <SEP> CH3 <SEP> C1 <SEP> H <SEP> -H;COOCH3 <SEP> X
<tb>  <SEP> 3
<tb> 84 <SEP> UH,-O- <SEP> CH3 <SEP> C1 <SEP> H <SEP> -CH;COOCH3 <SEP> U <SEP> Oel
<tb>  <SEP> 0113
<tb> 85 <SEP> CH3 <SEP> Br <SEP> - <SEP> CH3 <SEP> H <SEP> -bCH-COOCH3 <SEP> JD <SEP> Smp. <SEP> 83.1180
<tb> 86 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> H <SEP> -CCH;COOCH3 <SEP> zu <SEP> ss <SEP> r <SEP> Smp.90-920
<tb>  <SEP> 0113 <SEP> Ho <SEP> Br
<tb>   
EMI11.1     


<tb> Verb.

  <SEP> R1 <SEP> R7 <SEP> R8 <SEP> R9 <SEP> -X-R3 <SEP> R4 <SEP> Konstante
<tb>  <SEP> 87 <SEP> CH3 <SEP> CHC00CH3 <SEP> U <SEP> CH3 <SEP> .-CH3 <SEP> CH; <SEP> C <SEP> Smp.1130-114"
<tb>  <SEP> 88 <SEP> CH3 <SEP> H <SEP> Br <SEP> 4-OH <SEP> -CH;COOCH3 <SEP> U <SEP> Smp.135-140 
<tb>  <SEP> 3
<tb>  <SEP> 89 <SEP> CH3 <SEP> CH3 <SEP> 0113 <SEP> H <SEP> H <SEP> -CH;COOCH <SEP> 4;

  <SEP> l <SEP> mp.88-91 <SEP> Smp.88-910
<tb>  <SEP> -OH <SEP> -0000
<tb>  <SEP> 90 <SEP> CH3 <SEP> H <SEP> Br <SEP> ;-Br <SEP> CH3 <SEP> ssU <SEP> mp.134-13 <SEP> ,5
<tb>  <SEP> 0113
<tb>  <SEP> 91 <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> -CH2-CON° <SEP> 2 <SEP> X <SEP> Bri <SEP> j B <SEP> Smp <SEP> .132-1390
<tb>  <SEP> 92 <SEP> CH3 <SEP> CH3 <SEP> 0113 <SEP> H <SEP> -H11-O000113 <SEP> TI <SEP> 28 <SEP> 1.5280
<tb>  <SEP> 3
<tb>  <SEP> 93 <SEP> CH3 <SEP> H <SEP> Br <SEP> W-C1 <SEP> -CH-COOCH3 <SEP> Smp.143-145 
<tb>  <SEP> 3
<tb>  <SEP> 94 <SEP> Br <SEP> CH3 <SEP> CH3 <SEP> -Br <SEP> -CB-COOCB <SEP> Di <SEP> Smp.114-1220
<tb>  <SEP> 95 <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> - <SEP> AH;

  ;COOCH3 <SEP>  >  <SEP> C1 <SEP> Smp.126-132 
<tb>   
EMI12.1     


<tb> Verb <SEP>  >  <SEP> R <SEP> 1 <SEP> R7 <SEP> R8 <SEP> R9 <SEP> -X-R3 <SEP> R4 <SEP> Phys <SEP> kal
<tb>  <SEP> 96 <SEP> CH3 <SEP> H <SEP> C2H5 <SEP> CH; <SEP> U <SEP> Stnp.105-107
<tb>  <SEP> 0113 <SEP> 001
<tb>  <SEP> 97 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> 4-CH3 <SEP> -CHH3COOCH3 <SEP> 31i$LN01
<tb>  <SEP> 0113
<tb>  <SEP> 98 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> 4CH3 <SEP> -CtCOOCH3 <SEP> X <SEP> Br <SEP> Dmp.104-107 
<tb>  <SEP> 99 <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> 5-0113 <SEP> - <SEP> ;COOCH3 <SEP> X <SEP> Smp.119-122"
<tb>  <SEP> 3
<tb>  <SEP> 100 <SEP> CH3 <SEP> 11 <SEP> OH3 <SEP> | <SEP> CH;

  <SEP> 9 <SEP> | <SEP> mp.106-110
<tb>  <SEP> 0113
<tb>  <SEP> 101 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> 4-Br <SEP> -5H3COOCH3 <SEP> S <SEP> Smp.107-1080
<tb>  <SEP> 102 <SEP> CH3 <SEP> H <SEP> Cl <SEP> 4-C1 <SEP> -2H;COOCH3 <SEP> U <SEP> Smp.134-136 
<tb>  <SEP> 3
<tb>  <SEP> 103 <SEP> CH3 <SEP> H <SEP> C1 <SEP> 4-Br <SEP> -IH;COOCH3 <SEP> U <SEP> Smp.137-138 
<tb>  <SEP> 104 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> 4-C1 <SEP> -5H;COOCH3 <SEP> U <SEP> -Br <SEP> Smp.108-111 
<tb>  <SEP> 0113
<tb>    Ferner Verbindungen der Formel:
EMI13.1     

EMI13.2     


<tb> Verbl.
<tb>



  Verb <SEP> R <SEP> 1 <SEP> R <SEP> 2 <SEP> -x <SEP> -R3 <SEP> Konstante
<tb> 105 <SEP> CH3 <SEP> 6CH3 <SEP> -gH;COOCH3 <SEP> Stnp. <SEP> 90-92 
<tb> 1o6 <SEP> CH3 <SEP> 6-OH3 <SEP> -tH;COOC2H5 <SEP> Oel
<tb> 107 <SEP> CH3 <SEP> 6-C2H5 <SEP> -tH-COOCH3 <SEP> Oel
<tb>  <SEP> 3
<tb> 108 <SEP> CH3 <SEP> 6-1 <SEP> -gH-COOCH3 <SEP> Smp.102-104 
<tb>  <SEP> 3
<tb>    Ferner Verbindungen der Formel:
EMI14.1     

EMI14.2     


<tb>  <SEP> Verb. <SEP> R <SEP> R <SEP> .-X <SEP> -R <SEP> Physikal.
<tb>



   <SEP> 1 <SEP> 2 <SEP> 3 <SEP> Konstante
<tb> 109 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH;COOCH3 <SEP> Smp. <SEP> 136-1370
<tb>  <SEP> 3
<tb>  <SEP> 3
<tb> 110 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-COOC2H, <SEP> Oel
<tb>  <SEP> 3
<tb> 111 <SEP> CH3 <SEP> 6O2H5 <SEP> -H-COOCH3 <SEP> Oel
<tb>  <SEP> 0113
<tb> 112 <SEP> CH3 <SEP> 6-OH3 <SEP> -CH2-COOCH3
<tb> 113 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-CON(CH3) <SEP> Smp.172-1740
<tb> 114 <SEP> CH3 <SEP> 6-CH3 <SEP> -CHZ-CON( <SEP> viscos
<tb> 115 <SEP> CH3 <SEP> 4-CH3 <SEP> 4's <SEP> -CH;COOCH3 <SEP> Oel
<tb>  <SEP> 3
<tb> 116 <SEP> CH3 <SEP> 6-C1. <SEP> -CH-COOCH, <SEP> Smp.142-145"
<tb>  <SEP> 3
<tb>   
Die Verbindungen der Formel I können für sich allein oder zusammen mit geeigneten Trägern und/oder anderen Zuschlagstoffen verwendet werden.

  Geeignete Träger und Zuschlagstoffe können fest oder flüssig sein und entsprechen den in der Formulierungstechnik üblichen Stoffen wie z. B.



  natürlichen oder regenerierten mineralischen Stoffen, Lösungs-, Dispergier-, Netz-,   Haft-,      Verdickungs-,    Binde- oder Düngemitteln.



   Zur Applikation können die Verbindungen der Formel I in den folgenden Aufarbeitungsformen vorliegen:
Feste Aufarbeitungsformen:
Stäubemittel, Streumittel, Granulate, Umhüllungsgranulate, Imprägnierungsgranulate und Homogengranulate.



   Flüssige Aufarbeitungsformen: a) in Wasser dispergierbare Wirkstoffkonzentrate: Spritzpulver, Pasten, Emulsionen; b) Lösungen.



   Zur Herstellung fester Aufarbeitungsformen (Stäubemittel, Streumittel) werden die Wirkstoffe mit festen Trägerstoffen vermischt. Als Trägerstoffe kommen z. B. Kaolin, Talkum, Bolus, Löss, Kreide, Kalkstein, Kalkgries, Attapulgit, Dolomit, Diatomeenerde, gefällte Kieselsäure, Erdalkalisilikate, Natrium- und Kaliumaluminiumsilikate (Feldspäte und Glimmer), Calcium- und Magnesiumsulfate, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoff, gemahlene pflanzliche Produkte wie Getreidemehl, Baumrindenmehl, Holzmehl, Nussschalenmehl, Cellulosenpulver, Rückstände von Pflanzenextrakten, Aktivkohle usw., je für sich oder als Mischung untereinander in Frage.



   Die Korngrösse der Trägerstoffe beträgt für Stäubemit tel zweckmässig bis ca. 0,1 mm, für Streumittel ca. 0,075 bis 0,2 mm und für Granulate 0,2 mm oder mehr.



   Granulate lassen sich herstellen, indem man einen Wirkstoff der Formel I in einem organischen Lösungsmittel löst und die so erhaltene Lösung auf ein granuliertes Mineral, z. B. Attapulgit, SiO2, Granicalcium, Bentonit usw. aufbringt und dann das organische Lösungsmittel wieder verdampft.



   In Wasser dispergierbare Wirkstoffkonzentrate, d. h.



  Spritzpulver, Pasten und Emulsionskonzentrate stellen Mittel dar, die mit Wasser auf jede gewünschte Konzentration verdünnt werden können. Sie bestehen aus Wirkstoff, Trägerstoff, gegebenenfalls den Wirkstoff stabilisierenden Zusätzen, oberflächenaktiven Substanzen und Antischaummitteln und gegebenenfalls Lösungsmitteln.



   Die Wirkstoffkonzentration in diesen Mitteln beträgt 5% bis 80%. Spritzpulver und Pasten werden erhalten, indem man die Wirkstoffe mit Dispergiermitteln und pulverförmigen Trägerstoffen in geeigneten Vorrichtungen bis zur Homogenität vermischt und vermahlt. Als Trägerstoffe kommen beispielsweise die vorstehend für die festen Aufarbeitungsformen erwähnten in Frage. In manchen Fällen ist es vorteilhaft, Mischungen verschiedener Trägerstoffe zu verwenden.

  Als Dispergatoren können beispielsweise verwendet werden:
Kondensationsprodukte von sulfoniertem Naphthalin und sulfonierten Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäure mit Phenol und Formaldehyd sowie Alkali-, Ammonium- und Erdalkalisalze von Ligninsulfonsäure, weiter Alkylarylsulfonate, Alkali- und Erdalkalimetallsalze der Dibutylnaphthalinsulfonsäure, Fettalkoholsulfate, wie Salze sulfatierter Hexadecanole, Heptadecanole, Octadecanole und Salze von sulfatierten Fettalkoholglykoläthern, das Natriumsalz von Oleylmethyltaurid, ditertiäre Äthylenglykole, Dialkyldilaurylammoniumchlorid und fettsaure Alkali- und Erdalkalisalze.



   Als Antischaummittel kommen zum Beispiel Siliconöle in Frage.



   Die Wirkstoffe werden mit den oben aufgeführten Zusätzen so vermischt, vermahlen, gesiebt und passiert, dass bei den Spritzpulvern der feste Anteil eine Korngrösse von 0,02 bis 0,04 mm und bei den Pasten von 0,03 mm nicht   überschrei    tet. Zur Herstellung von Emulsionskonzentraten und Pasten werden Dispergiermittel, wie sie in den vorangehenden Abschnitten aufgeführt wurden, organische Lösungsmittel und Wasser verwendet.



   Der Gehalt an Wirkstoff in den oben beschriebenen Mitteln liegt zwischen 0,1 bis   95 /0.   



   Emulgierbare Konzentrate:
Zur Herstellung eines   250/,eigen    emulgierbaren Konzentrates werden folgende Stoffe verwendet:
5 Teile Wirkstoff
2,5 Teile epoxydiertes Pflanzenöl 10 Teile eines   AlkylarylsulfonatlFettalkohol-    polyglykoläther-Gemisches
5 Teile Dimethylformamid 57,5 Teile Xylol.



   PATENTANSPRUCH I
Verfahren zur Herstellung von heterocyclischen Carbonsäureaniliden der Formel I
EMI15.1     
 worin   Rl      Cl-C4-Alkyl,      Cl-C4-Alkoxy    oder Halogen, R2 Wasserstoff,   Ct-C3-Alkyl    oder Halogen,   R5    Wasserstoff, C1-C3-Alkyl oder Halogen,   R5    Wasserstoff oder Methyl sind, wobei die Gesamtzahl von C-Atomen der Substituenten   Rl,    R2, R5 und   R6    im Phenylring die Zahl 8 nicht übersteigt,
EMI15.2     
 darstellen, wobei R',   R"    und R"' unabhängig voneinander Wasserstoff, Methyl oder Äthyl bedeuten und R4 einen unsubstituierten oder durch Methyl und/oder Halogen substituierten 5oder 6-gliedrigen heterocyclischen Rest mit 1 oder 2 Heteroatomen bedeutet, 

   gekennzeichnet durch Überführung einer Verbindung der Formel II bei   -20"    bis   +180 "C.   
EMI15.3     




  mit Butyl-Lithium, Na-Hydrid oder   K2CO3    in Pyridin oder Te 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.



   



  
 



   The present invention relates to a process for the preparation of new anilides which correspond to formula I.
EMI1.1
 .Worin Rl C1-C4-alkyl, Cl-C4-alkoxy or halogen, R2 hydrogen, C1-C3-alkyl or halogen, R5 hydrogen, Cl-C3-alkyl or halogen, R6 hydrogen or methyl, where the The total number of carbon atoms in the substituents R1, R2, R5 and R6 in the phenyl ring does not exceed 8,
EMI1.2
 represent, where R ', R "and R"' are independently hydrogen, methyl or ethyl and R4 is a 5 or 6-membered heterocyclic radical with 1 or 2 heteroatoms which is optionally substituted by methyl and / or halogen.



   By alkyl and as alkyl: ell an alkoxy group, depending on the number of carbon atoms specified, the following groups are to be understood: methyl, ethyl, n-propyl, iso-propyl or n-, iso-, sec- or tert-butyl. Fluorine, chlorine, bromine or iodine are suitable as halogen.



   As a 5- to 6-membered heterocyclic radical, for. B.



  The following are mentioned: furan, thiophene, pyridine, pyrimidine, 2,3-dihydro-4H-pyran, 1,4-oxathi- (2> yne, tetrahydrofuran, morpholine or piperidine, which can optionally be substituted by methyl and / or halogen.



   According to the invention, the compounds of the formula I are prepared such that the corresponding acylanilide of the formula II
EMI1.3
 with butyl-lithium, sodium hydride or K2CO3 in pyridine or tetrahydrofuran is converted into the alkali salt, which is then mixed with the haloacetic acid ester or amide or the a-halopropionic acid ester or amide of the formula III
Hal-X-R3 (III) is further implemented.



   In formulas II and III, R1 to R6 and X have those for
Formula I given meanings, while Hal represents a halogen atom, preferably chlorine or bromine.



   The reactions can also be inert towards the reactants in the presence or absence of further ones
Solvents or diluents are carried out. For example, the following are possible: Aliphatic or aromatic hydrocarbons such as benzene, toluene, xylenes,
Petroleum ether, ether and ethereal compounds such as dialky ether or dioxane, or even nitriles such as acetonitrile; and
Mixtures of such solvents with one another.



   The reaction temperatures are between -20 "C and
180 "C, preferably between 0 and 120" C.



   The compounds of formula I have the property, the growth and the state of health of farm animals and the growth and development of useful plants and the cultivation of useful plants, e.g. B. through selective weed control or through growth regulation to influence favorably. Among other things, they are suitable for combating various plant and animal pests.



   However, the compounds of the formula I achieve an outstanding effect as plant fungicides. They are formulated into appropriate agents with the usual carriers. The compounds of the formula I in which X is -CH (CH3) - have an asymmetric carbon atom and can be split into optical antipodes in the usual way. Here, the enantiomeric D-form has the stronger plant fungicidal effect.



   The following example serves to explain the invention in more detail without restricting the same. The temperature data in the example and in the following tables refer to degrees Celsius.



   example
A suspension is prepared from 2.4 g (0.055 mol) of 55/0 sodium hydride oil dispersion and 25 ml of tetrahydrofuran. 10.75 g (0.05%) are added dropwise to this at room temperature
Moles) in 125 ml of tetrahydrofuran dissolved furan-2-carboxylic acid re-2 ', 6'-dimethylanilide, m.p. 125-128, which is obtained by reacting 2,6-dimethylaniline with z. B. 2-furanoyl chloride has won. The reaction mixture is then stirred for 30 minutes at normal temperature and for a further 30 minutes at 45.degree.



  After cooling, 9.2 g (0.055 mol) of methyl 2-bromopropionate, dissolved in 10 ml of tetrahydrofuran, are added dropwise at room temperature. The mixture is then stirred for 1 hour at normal temperature and heated under reflux for 24 hours.



  After cooling, it is filtered and the filtrate is concentrated on a rotary evaporator. The N- (1¯-methoxycarbonyl-ethyl) -N- (furan- (2 '-carbonyl2,6-dimethylaniline) which remains as residue is recrystallized from ether / petroleum ether;



  82-84 "C.



  The following connections can be made in the same way:
EMI2.1

EMI2.2


<tb> VeLb. <SEP> R, <SEP> R2 <SEP> -X'R3 <SEP> Physical.
<tb>



   <SEP> r <SEP> constant
<tb> <SEP> ¯¯ <SEP>. <SEP>
<tb> 1 <SEP> CH, <SEP> 6-H <SEP> -CH-COOCH3 <SEP> Smp. <SEP> 85-870
<tb> 2 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CH-COOCH3 <SEP> Sdp. <SEP> 162-163 /
<tb> <SEP> cH3 <SEP> 0.1 <SEP> Torr
<tb> 3 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-COO-C2H5 <SEP> m.p. <SEP> 90-940
<tb> <SEP> CH3
<tb> 4 <SEP> CH3 <SEP> H <SEP> -CH <SEP> -COOCH. <SEP> Sdp. <SEP> 126-148 /
<tb> <SEP> CH3 <SEP> 0.02 <SEP> Torr
<tb> 5 <SEP> CH3 <SEP> 3-CH3 <SEP> -CH-COOCH3 <SEP> Sdp. 151 / 0.03 Torr
<tb> <SEP> CH3
<tb> 6 <SEP> CH3 <SEP> 4-CH3 <SEP> -0H-COOCH3 <SEP> Smp. <SEP> 89-91
<tb> <SEP> cH3
<tb> 7 <SEP> CH3 <SEP> 5-CH3 <SEP> -CH-COOCH3 <SEP> Smp.

  <SEP> 114-116
<tb> <SEP> CH3
<tb> <SEP> CD) <SEP> -F'orm
<tb> 8 <SEP> CR3 <SEP> 6-cH3 <SEP> cH? C00CH3 <SEP> SmO2 <SEP> 1030
<tb> <SEP> 3 <SEP> 3 <SEP> bH3 <SEP> [1g "<SEP> -47.0 + 0.7;
<tb> <SEP> c-1.73% <SEP> g / v <SEP> in
<tb> <SEP> acetone
<tb> 9 <SEP> CH3 <SEP> 6-C2H5 <SEP> -ÇH2-COOCH3 <SEP> m.p. <SEP> 91-94
<tb> 10 <SEP> CR3 <SEP> 6-Cl <SEP> -CR-COOC <SEP> Smp.
<tb>



   <SEP> H3 <SEP> 2 <SEP> 5 <SEP> Smp. <SEP> 112-113
<tb>
EMI3.1


<tb> Connection <SEP> R1 <SEP> R2 <SEP> wX-R3 <SEP> IConstante
<tb> <SEP> 11 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-CO-NH, <SEP> m.p. 128-130
<tb> <SEP> 12 <SEP> C1 <SEP> 5-C1 <SEP> -CH-COOCH3 <SEP> Smp. 11O-1120
<tb> <SEP> CR3
<tb> <SEP> 13 <SEP> C2H5 <SEP> 6-C2H5 <SEP> -CH2-CO-NH2 <SEP> m.p. 127-1280
<tb> <SEP> 14 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOCH3 <SEP> Smp. <SEP> 92
<tb> <SEP> CR3
<tb> <SEP> 15 <SEP> nC4H9-O- <SEP> H <SEP> -ICH-COOCH3 <SEP> Sdp.170-173 /
<tb> <SEP> CH3 <SEP> 0.04 <SEP> Torr
<tb> <SEP> 16 <SEP> CH3 <SEP> 6CH3 <SEP> -CH; CO-NHCH3 <SEP> Smp. <SEP> 141-143
<tb> <SEP> CR
<tb> <SEP> 3
<tb> <SEP> 17 <SEP> iso-C3H7 <SEP> 6-isoC3H7 <SEP> -CH-COOCH <SEP> Smp.

  <SEP> 86-960
<tb> <SEP> 18 <SEP> iso-C3H7 <SEP> H <SEP> -CH-COOCH3 <SEP> Sdp.1580 / O, O3Torr
<tb> <SEP> OH3
<tb> <SEP> 19 <SEP> F <SEP> H <SEP> -CH-COOCH3 <SEP> Sdp.l500 / 0.03Torr
<tb> <SEP> OH3
<tb> <SEP> 20 <SEP> C1 <SEP> H <SEP> 0111 <SEP>; COOCH3 <SEP> Sdp.1550 / O, O5Torr
<tb> <SEP> CR3
<tb> <SEP> 21 <SEP> C1 <SEP> 6-C1 <SEP> 'CH-COOCH3 <SEP> Smp. 113-1160
<tb> <SEP> CR3
<tb>
EMI4.1


<tb> <SEP> Verb <SEP>. <SEP> R <SEP> R <SEP> PhysLkal.
<tb>



   <SEP> 1 <SEP> 2 <SEP> -X-R3 <SEP> constant
<tb> 22 <SEP> J <SEP> H <SEP> -CH-COOCH3 <SEP> Sdp.145 <SEP> / 0.2 Torr
<tb> <SEP> 1 <SEP> 3
<tb> 2-3 <SEP> Br <SEP> H <SEP> -H-COOCH3 <SEP> Sdp.1450 / 0.05 Torr
<tb> <SEP> CH3
<tb> 24 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-COOCH3 <SEP> Smp. <SEP> 98-990
<tb> 25 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-C0-NHCH3 <SEP> m.p. 164-1650
<tb> 26 <SEP> CH3 <SEP> 6-OH3 <SEP> -CH2-CO-N (CH3)> <SEP> m.p. 142-1450
<tb> 27 <SEP> cd <SEP> 4-CH30- <SEP> -011-000CH3 <SEP>; <SEP> Sdp <SEP> 168 Sdp.1680
<tb> <SEP> OH3 <SEP> 4-CH, O- <SEP> / 0.07 Torr
<tb> 28 <SEP> CH3 <SEP> W-sec.C4H90 <SEP> -CH-COOCH3 <SEP> Sdp.l780 <SEP> /
<tb> <SEP> O, OSTorr.
<tb>



  29 <SEP> 02H5 <SEP> 6-C2H5 <SEP> -CH2-C0-CHi2 <SEP> zu2 <SEP> mp 178-181
<tb> 30 <SEP> 02H5 <SEP> 6-C2H5 <SEP> -CH2-COOCH3 <SEP> Smp. <SEP> 880
<tb> 31 <SEP> 02H5 <SEP> 6-C2H5 <SEP> -CH2-C0-NHC2H5 <SEP> m.p. <SEP> 158-159
<tb> Furthermore also compounds of the formula
EMI5.1

EMI5.2


<tb> Connection <SEP> R <SEP> R2 <SEP> -X-R3 <SEP> Physical.
<tb>



   <SEP> 1
<tb> <SEP> I <SEP> Constants
<tb> 33 <SEP> CH3 <SEP> 6-CH3 <SEP> -CR-000CR3 <SEP> (D) <SEP> form
<tb> <SEP> Smp. <SEP> 91.920
<tb> <SEP> CH3 <SEP> Smp <SEP> 91-92
<tb> <SEP> D <SEP> a <SEP> to + 0.80;
<tb> <SEP> c = 1.52% <SEP> g / v <SEP> in
<tb> <SEP> acetone
<tb> 34 <SEP> CH3 <SEP> 6cH3 <SEP> -CH2'co <SEP> -N <SEP> (CH <SEP> Oel
<tb> 35 <SEP> C2H5 <SEP> 6-C2H5 <SEP> -CH2-C0-NH2 <SEP> m.p. 144-1450
<tb> <SEP> 36 <SEP> CH3 <SEP> 6-C1 <SEP> -H-COO-C2H5 <SEP> oil
<tb> <SEP> 3
<tb> <SEP> 37 <SEP> CH3 <SEP> li-sec.C, H <SEP> -O- <SEP> -yH-COOCH3 <SEP> Sdp.1850 / 0, O6Torr
<tb> <SEP> 3
<tb> <SEP> 38 <SEP> F <SEP> H <SEP> -C1H-COOCH3 <SEP> Sdp.1620 / O, lTorr
<tb> <SEP> 3
<tb> <SEP> 39 <SEP> C1 <SEP> H <SEP> -IH-COOCH3 <SEP> Sdp.1600 / 0, lTorr
<tb> <SEP> CH3
<tb> <SEP> 40 <SEP> J <SEP> H <SEP> -fH-COOCH3 <SEP> Sdp.168-172 /
<tb> <SEP> CH3 <SEP>), 1 <SEP> Torr
<tb> <SEP> 41 <SEP>

   CH3 <SEP> 4-CH3 <SEP> -CH-COOCH3
<tb> <SEP> 3 <SEP>), 2 <SEP> Torr
<tb> <SEP> 3 <SEP> 2 <SEP> Torr
<tb> <SEP> 42 <SEP> CH3 <SEP> 6-C1 <SEP> -7H-COOCH3 <SEP> Smp. <SEP> 80-87
<tb> <SEP> OH3
<tb> Furthermore the compounds of the general formula:
EMI6.1

EMI6.2


<tb> Verb. <SEP> R <SEP> R2 <SEP> -X-R3 <SEP> R4 <SEP> 1 <SEP> .Phys <SEP> ika <SEP> 1.
<tb>



   <SEP> 1 <SEP> const
<tb> <SEP> 43 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-COOCH3 <SEP> t <SEP> Smp.95-96
<tb> <SEP> 44 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOCH3 <SEP> 4 <SEP> Smp. 85-87
<tb> <SEP> 45 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOC2H5 <SEP> t <SEP> Smp. <SEP> 63-66
<tb> <SEP> 0113
<tb> <SEP> 46 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CH2-COOCH3 <SEP> t <SEP> Smp. <SEP> 88-90
<tb> <SEP> 47 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-CON (CH3) 2 <SEP> t <SEP> Smp. <SEP> 148-152
<tb> <SEP> 48 <SEP> CH3 <SEP> 6-CH3 <SEP> -OH-OOOCH3 <SEP> m.p. 100-107
<tb> <SEP> OH3 <SEP> H3C0
<tb> <SEP> 49 <SEP> CH3 <SEP> 6 <SEP> -02H5 <SEP> -CH2-COOCH3 <SEP> X <SEP> n25 <SEP> e <SEP> 1.5276
<tb> <SEP> 50 <SEP> 01130 <SEP> 6-C1 <SEP> -CH; COOCH3 <SEP> S <SEP> n <SEP> Smp. <SEP> 98 <SEP> - <SEP> 100
<tb> <SEP> 0113
<tb>
EMI7.1


<tb> connection <SEP> R1 <SEP> R2 <SEP> -X-R3 <SEP> R4 <SEP> physical.
<tb>



   <SEP> constant
<tb> 51 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-COOCH3 <SEP> 3¸ <SEP> Smp. <SEP> 50.510
<tb> 52 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-COOCH3 <SEP> -71mp.97-980
<tb> <SEP> CR3
<tb> 53 <SEP> H3 <SEP> 6-1 <SEP> -CH-COOCH3 <SEP> Smp. 73-85o
<tb> <SEP> OH3
<tb> 54 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CH2-COOCII3 <SEP> Däl <SEP> Smp. 76-770
<tb> <SEP> 0
<tb> 55 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOCH3 <SEP> X <SEP> O <SEP> J <SEP> Smp. 108-110
<tb> <SEP> 3 <SEP> 0
<tb> 56 <SEP> H3 <SEP> 6-CH3 <SEP> -C1-COOCH3 <SEP> XJ <SEP> Smp. <SEP> 138
<tb> <SEP> OH3 <SEP> -CH-COOCH <SEP> 0
<tb> <SEP> 20
<tb> 57 <SEP> isoC3H7 <SEP> 6-isoC3H7 <SEP> -CH-COOCH3 <SEP> JW <SEP> O <SEP>; <SEP> CH3 <SEP> nD <SEP> 1.6900
<tb> <SEP> C1H3 <SEP> 0 <SEP> CH3
<tb> 58 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOCH3 <SEP> X <SEP> Css <SEP> Smp. 120-122
<tb> 59 <SEP> H3 <SEP> 6-CH3 <SEP> -CH-COOCH3 <SEP> z <SEP> 8 <SEP> Smp.

  <SEP> 91-930
<tb> <SEP> 3 <SEP> 00113
<tb> <SEP> CH3 <SEP> 00113
<tb>
EMI8.1


<tb> Connection <SEP> h <SEP> R2 <SEP> -X-R3 <SEP> R4 <SEP> PhysLkal
<tb> <SEP> 60 <SEP> CH3 <SEP> 6-C1 <SEP> -F "" "" "<SEP>>) <SEP> smp. <SEP> 11
<tb> <SEP> OH3
<tb> <SEP> 61 <SEP> CH3 <SEP> 6-C1 <SEP>; <SEP> ICH-COOCH3 <SEP> oD;) <SEP> X <SEP> 9 <SEP> Smp. 118-1190
<tb> <SEP> 62 <SEP> CH3 <SEP> 6-C1 <SEP> -tH-COOC2H5 <SEP> C <SEP> X3 <SEP> Smp. <SEP> 1260
<tb> <SEP> 63 <SEP> CH3 <SEP> 6-C1 <SEP> -CH-COOCK, <SEP> 4 <SEP> Stnp. 150-1510
<tb> 64 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-COOCH3 <SEP> CH- <SEP> ° <SEP> O <SEP> 3 <SEP> Smp. <SEP> 81-830
<tb> 65 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CY-COOCH, <SEP> Sdp.

  <SEP> Sdp.190-2100
<tb> <SEP> Olis <SEP> / 0.5 <SEP> Torr
<tb> 66 <SEP> CH3 <SEP> 6-C2H5 <SEP> -CH2-COOCH3 <SEP> to <SEP>) <SEP> Sdp.190-195
<tb> <SEP> CR30 <SEP> / 0.2 <SEP> / 0.2 <SEP> / 0.2 <SEP> Torr
<tb> 67 <SEP> CH3 <SEP> 6-CH3 <SEP> - <SEP> -CH2-COOCH3 <SEP> 7 <SEP> Smp. <SEP> 75o
<tb> 68 <SEP> CH3 <SEP> 6-CH3 <SEP> -8H-COOCH3 <SEP> rO <SEP> g <SEP> Smp. <SEP> 83-85
<tb> <SEP> OH3
<tb>
EMI9.1


<tb> <SEP> Physical.
<tb>



  Conn. <SEP> RL <SEP> R2 <SEP> -X-R3 <SEP> R4 <SEP> constant
<tb> <SEP> 69 <SEP> CH3 <SEP> 6-C1 <SEP> -iH-COOCH3 <SEP> es <SEP> Smp. <SEP> 90-1050
<tb> <SEP> 0113 <SEP> 11
<tb> <SEP> 70 <SEP> C1 <SEP> I <SEP> 6-C1 <SEP> -CH-COOCH <SEP> oil
<tb> <SEP> OH3 <SEP> 0
<tb> <SEP> 71 <SEP> CH3-0- <SEP> H <SEP> -CH2-CONH2 <SEP> S <SEP> oil
<tb> <SEP> 72 <SEP> CH3 <SEP> 4-C1 <SEP> CH3 <SEP> n <SEP> oil
<tb> <SEP> 0113
<tb> <SEP> 73 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-COOCH <SEP> CH; <SEP> CH <SEP> X <SEP> CH3 <SEP> Smp. 91-93
<tb> <SEP> 74 <SEP> C1 <SEP> 5-C1 <SEP> -ICH-COOCH3 <SEP> | <SEP> oil
<tb> <SEP> iacx
<tb> <SEP> 75 <SEP> Cl <SEP> 5-C1 <SEP> -CH-COOCH3 <SEP> CH3 <SEP> t <SEP> oil
<tb> <SEP> LH3 <SEP> OH
<tb> <SEP> 76 <SEP> CH3 <SEP> 6-CH3 <SEP> -H-COOCH3 <SEP> X <SEP> Smp.

  <SEP> 99-100 "
<tb> <SEP> CH3 <SEP> Ho
<tb> <SEP> 77 <SEP> CH3 <SEP> 6-CH3 <SEP> -CR-C0OCR <SEP> X <SEP> O <SEP> 3 <SEP> Stnp. <SEP> 1300
<tb> <SEP> 3
<tb> <SEP> OH3 <SEP> 011o
<tb> <SEP> 78 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-CO-NH <SEP> m.p. <SEP> 85-88
<tb> <SEP> O2H5 <SEP> 3o
<tb> Furthermore, the compounds of the general formula Ia
EMI10.1

EMI10.2


<tb> <SEP> IFhysLkal.
<tb>

 

  79 <SEP> | <SEP> CH3 <SEP> CH3 <SEP> 1 <SEP> H <SEP> JHH3CO <SEP> 3 <SEP> JÜ
<tb> 80 <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> 5CH3 <SEP> -CH-COOCH3 <SEP> Smp. <SEP> 83.5
<tb> <SEP> 113 <SEP> 850
<tb> 81 <SEP> CH3 <SEP> CH3 <SEP> 02115 <SEP> H <SEP> -cClH; COOCH3 <SEP> 2C <SEP> Smp12o66
<tb> 82 <SEP> C2H5 <SEP> CH3 <SEP> CH3 <SEP> lI <SEP> -2H-COOCH3 <SEP> U <SEP> Sdp. <SEP> l76
<tb> <SEP> H3 <SEP> O <SEP> 177 / 0.05 Torr
<tb> 83 <SEP> CH3 <SEP> CH3 <SEP> C1 <SEP> H <SEP> -H; COOCH3 <SEP> X
<tb> <SEP> 3
<tb> 84 <SEP> UH, -O- <SEP> CH3 <SEP> C1 <SEP> H <SEP> -CH; COOCH3 <SEP> U <SEP> oil
<tb> <SEP> 0113
<tb> 85 <SEP> CH3 <SEP> Br <SEP> - <SEP> CH3 <SEP> H <SEP> -bCH-COOCH3 <SEP> JD <SEP> Smp. <SEP> 83.1180
<tb> 86 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> H <SEP> -CCH; COOCH3 <SEP> to <SEP> ss <SEP> r <SEP> Smp.90-920
<tb> <SEP> 0113 <SEP> Ho <SEP> Br
<tb>
EMI11.1


<tb> verb.

  <SEP> R1 <SEP> R7 <SEP> R8 <SEP> R9 <SEP> -X-R3 <SEP> R4 <SEP> constant
<tb> <SEP> 87 <SEP> CH3 <SEP> CHC00CH3 <SEP> U <SEP> CH3 <SEP>.-CH3 <SEP> CH; <SEP> C <SEP> Smp. 1130-114 "
<tb> <SEP> 88 <SEP> CH3 <SEP> H <SEP> Br <SEP> 4-OH <SEP> -CH; COOCH3 <SEP> U <SEP> mp 135-140
<tb> <SEP> 3
<tb> <SEP> 89 <SEP> CH3 <SEP> CH3 <SEP> 0113 <SEP> H <SEP> H <SEP> -CH; COOCH <SEP> 4;

  <SEP> l <SEP> mp.88-91 <SEP> mp.88-910
<tb> <SEP> -OH <SEP> -0000
<tb> <SEP> 90 <SEP> CH3 <SEP> H <SEP> Br <SEP>; -Br <SEP> CH3 <SEP> ssU <SEP> mp.134-13 <SEP>, 5
<tb> <SEP> 0113
<tb> <SEP> 91 <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> -CH2-CON ° <SEP> 2 <SEP> X <SEP> Bri <SEP> j B <SEP > Smp <SEP> .132-1390
<tb> <SEP> 92 <SEP> CH3 <SEP> CH3 <SEP> 0113 <SEP> H <SEP> -H11-O000113 <SEP> TI <SEP> 28 <SEP> 1.5280
<tb> <SEP> 3
<tb> <SEP> 93 <SEP> CH3 <SEP> H <SEP> Br <SEP> W-C1 <SEP> -CH-COOCH3 <SEP> Smp. 143-145
<tb> <SEP> 3
<tb> <SEP> 94 <SEP> Br <SEP> CH3 <SEP> CH3 <SEP> -Br <SEP> -CB-COOCB <SEP> Di <SEP> Smp. 114-1220
<tb> <SEP> 95 <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> H <SEP> - <SEP> AH;

  ; COOCH3 <SEP>> <SEP> C1 <SEP> mp 126-132
<tb>
EMI12.1


<tb> Verb <SEP>> <SEP> R <SEP> 1 <SEP> R7 <SEP> R8 <SEP> R9 <SEP> -X-R3 <SEP> R4 <SEP> Phys <SEP> cal
<tb> <SEP> 96 <SEP> CH3 <SEP> H <SEP> C2H5 <SEP> CH; <SEP> U <SEP> Stnp.105-107
<tb> <SEP> 0113 <SEP> 001
<tb> <SEP> 97 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> 4-CH3 <SEP> -CHH3COOCH3 <SEP> 31i $ LN01
<tb> <SEP> 0113
<tb> <SEP> 98 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> 4CH3 <SEP> -CtCOOCH3 <SEP> X <SEP> Br <SEP> Dmp.104-107
<tb> <SEP> 99 <SEP> CH3 <SEP> CH3 <SEP> CH3 <SEP> 5-0113 <SEP> - <SEP>; COOCH3 <SEP> X <SEP> Smp. 119-122 "
<tb> <SEP> 3
<tb> <SEP> 100 <SEP> CH3 <SEP> 11 <SEP> OH3 <SEP> | <SEP> CH;

  <SEP> 9 <SEP> | <SEP> mp.106-110
<tb> <SEP> 0113
<tb> <SEP> 101 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> 4-Br <SEP> -5H3COOCH3 <SEP> S <SEP> Smp. 107-1080
<tb> <SEP> 102 <SEP> CH3 <SEP> H <SEP> Cl <SEP> 4-C1 <SEP> -2H; COOCH3 <SEP> U <SEP> Smp. 134-136
<tb> <SEP> 3
<tb> <SEP> 103 <SEP> CH3 <SEP> H <SEP> C1 <SEP> 4-Br <SEP> -IH; COOCH3 <SEP> U <SEP> Smp. 137-138
<tb> <SEP> 104 <SEP> CH3 <SEP> H <SEP> CH3 <SEP> 4-C1 <SEP> -5H; COOCH3 <SEP> U <SEP> -Br <SEP> Smp. 108-111
<tb> <SEP> 0113
<tb> Also compounds of the formula:
EMI13.1

EMI13.2


<tb> Rem.
<tb>



  Verb <SEP> R <SEP> 1 <SEP> R <SEP> 2 <SEP> -x <SEP> -R3 <SEP> constant
<tb> 105 <SEP> CH3 <SEP> 6CH3 <SEP> -gH; COOCH3 <SEP> Stnp. <SEP> 90-92
<tb> 1o6 <SEP> CH3 <SEP> 6-OH3 <SEP> -tH; COOC2H5 <SEP> oil
<tb> 107 <SEP> CH3 <SEP> 6-C2H5 <SEP> -tH-COOCH3 <SEP> oil
<tb> <SEP> 3
<tb> 108 <SEP> CH3 <SEP> 6-1 <SEP> -gH-COOCH3 <SEP> Smp. 102-104
<tb> <SEP> 3
<tb> Also compounds of the formula:
EMI14.1

EMI14.2


<tb> <SEP> Connection <SEP> R <SEP> R <SEP>.-X <SEP> -R <SEP> Physical.
<tb>



   <SEP> 1 <SEP> 2 <SEP> 3 <SEP> constant
<tb> 109 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH; COOCH3 <SEP> Smp. <SEP> 136-1370
<tb> <SEP> 3
<tb> <SEP> 3
<tb> 110 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH-COOC2H, <SEP> oil
<tb> <SEP> 3
<tb> 111 <SEP> CH3 <SEP> 6O2H5 <SEP> -H-COOCH3 <SEP> oil
<tb> <SEP> 0113
<tb> 112 <SEP> CH3 <SEP> 6-OH3 <SEP> -CH2-COOCH3
<tb> 113 <SEP> CH3 <SEP> 6-CH3 <SEP> -CH2-CON (CH3) <SEP> mp 172-1740
<tb> 114 <SEP> CH3 <SEP> 6-CH3 <SEP> -CHZ-CON (<SEP> viscos
<tb> 115 <SEP> CH3 <SEP> 4-CH3 <SEP> 4's <SEP> -CH; COOCH3 <SEP> oil
<tb> <SEP> 3
<tb> 116 <SEP> CH3 <SEP> 6-C1. <SEP> -CH-COOCH, <SEP> mp 142-145 "
<tb> <SEP> 3
<tb>
The compounds of the formula I can be used alone or together with suitable carriers and / or other additives.

  Suitable carriers and additives can be solid or liquid and correspond to the substances customary in formulation technology such as. B.



  natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers.



   For administration, the compounds of the formula I can be in the following working-up forms:
Fixed processing forms:
Dusts, grit, granulates, coating granulates, impregnation granulates and homogeneous granulates.



   Liquid working-up forms: a) active ingredient concentrates dispersible in water: wettable powders, pastes, emulsions; b) Solutions.



   The active ingredients are mixed with solid carriers for the production of solid forms (dusts, grit). As carriers come z. B. kaolin, talc, bolus, loess, chalk, limestone, lime grit, attapulgite, dolomite, diatomaceous earth, precipitated silica, alkaline earth silicates, sodium and potassium aluminum silicates (feldspars and mica), calcium and magnesium sulfates, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate , Ammonium phosphate, ammonium nitrate, urea, ground vegetable products such as grain flour, tree bark flour, wood flour, nut shell flour, cellulose powder, residues of plant extracts, activated charcoal etc., each individually or as a mixture with one another.



   The grain size of the carrier materials is expediently up to approx. 0.1 mm for dusts, approx. 0.075 to 0.2 mm for grit and 0.2 mm or more for granulates.



   Granules can be produced by dissolving an active ingredient of the formula I in an organic solvent and applying the resulting solution to a granulated mineral, e.g. B. attapulgite, SiO2, granicalcium, bentonite, etc. applies and then the organic solvent evaporates again.



   Active ingredient concentrates dispersible in water, d. H.



  Wettable powders, pastes and emulsion concentrates are agents that can be diluted with water to any desired concentration. They consist of active ingredient, carrier, optionally additives stabilizing the active ingredient, surface-active substances and anti-foaming agents and optionally solvents.



   The active ingredient concentration in these agents is 5% to 80%. Wettable powders and pastes are obtained by mixing the active ingredients with dispersants and pulverulent carriers in suitable devices until homogeneous and grinding. Suitable carriers are, for example, those mentioned above for the solid work-up forms. In some cases it is advantageous to use mixtures of different carriers.

  The following can be used as dispersants, for example:
Condensation products of sulfonated naphthalene and sulfonated naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde and alkali, ammonium and alkaline earth salts of ligninsulfonic acid, further alkylarylsulfonates, alkali metal and alkaline earth metal sulfanates, alkali metal sulfanates, alkali metal sulfanates, hexadeceptyl sulfonates, hexadeceptyl sulfonates, hexadeceptyl sulfonates, hexadeceptyl sulfonates, hexadeceptyl sulfonates, hexadeceptyl sulfonates, hexadeceptyl sulfonic acid salts , Octadecanols and salts of sulfated fatty alcohol glycol ethers, the sodium salt of oleyl methyl tauride, ditertiary ethylene glycols, dialkyldilaurylammonium chloride and fatty acid alkali and alkaline earth salts.



   Silicone oils, for example, can be used as antifoam agents.



   The active ingredients are mixed, ground, sieved and passed with the additives listed above in such a way that the solid portion of the wettable powders does not exceed a particle size of 0.02 to 0.04 mm and of the pastes of 0.03 mm. To produce emulsion concentrates and pastes, dispersants such as those listed in the previous sections, organic solvents and water are used.



   The content of active ingredient in the agents described above is between 0.1 and 95/0.



   Emulsifiable concentrates:
The following substances are used to produce a 250 /, self-emulsifiable concentrate:
5 parts of active ingredient
2.5 parts epoxidized vegetable oil 10 parts of an alkylarylsulfonate / fatty alcohol polyglycol ether mixture
5 parts of dimethylformamide, 57.5 parts of xylene.



   PATENT CLAIM I
Process for the preparation of heterocyclic carboxylic acid anilides of the formula I.
EMI15.1
 wherein Rl is Cl-C4-alkyl, Cl-C4-alkoxy or halogen, R2 is hydrogen, Ct-C3-alkyl or halogen, R5 is hydrogen, C1-C3-alkyl or halogen, R5 is hydrogen or methyl, the total number of C- Atoms of the substituents Rl, R2, R5 and R6 in the phenyl ring does not exceed the number 8,
EMI15.2
 represent, where R ', R "and R"' are independently hydrogen, methyl or ethyl and R4 is a 5 or 6-membered heterocyclic radical with 1 or 2 heteroatoms, which is unsubstituted or substituted by methyl and / or halogen,

   characterized by conversion of a compound of formula II at -20 "to +180" C.
EMI15.3




  with butyl lithium, sodium hydride or K2CO3 in pyridine or Te

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. Die Verbindungen der Formel I können für sich allein oder zusammen mit geeigneten Trägern und/oder anderen Zuschlagstoffen verwendet werden. Geeignete Träger und Zuschlagstoffe können fest oder flüssig sein und entsprechen den in der Formulierungstechnik üblichen Stoffen wie z. B. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. The compounds of the formula I can be used alone or together with suitable carriers and / or other additives. Suitable carriers and additives can be solid or liquid and correspond to the substances customary in formulation technology such as. B. natürlichen oder regenerierten mineralischen Stoffen, Lösungs-, Dispergier-, Netz-, Haft-, Verdickungs-, Binde- oder Düngemitteln. natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Zur Applikation können die Verbindungen der Formel I in den folgenden Aufarbeitungsformen vorliegen: Feste Aufarbeitungsformen: Stäubemittel, Streumittel, Granulate, Umhüllungsgranulate, Imprägnierungsgranulate und Homogengranulate. For administration, the compounds of the formula I can be in the following working-up forms: Fixed processing forms: Dusts, grit, granulates, coating granulates, impregnation granulates and homogeneous granulates. Flüssige Aufarbeitungsformen: a) in Wasser dispergierbare Wirkstoffkonzentrate: Spritzpulver, Pasten, Emulsionen; b) Lösungen. Liquid working-up forms: a) active ingredient concentrates dispersible in water: wettable powders, pastes, emulsions; b) Solutions. Zur Herstellung fester Aufarbeitungsformen (Stäubemittel, Streumittel) werden die Wirkstoffe mit festen Trägerstoffen vermischt. Als Trägerstoffe kommen z. B. Kaolin, Talkum, Bolus, Löss, Kreide, Kalkstein, Kalkgries, Attapulgit, Dolomit, Diatomeenerde, gefällte Kieselsäure, Erdalkalisilikate, Natrium- und Kaliumaluminiumsilikate (Feldspäte und Glimmer), Calcium- und Magnesiumsulfate, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoff, gemahlene pflanzliche Produkte wie Getreidemehl, Baumrindenmehl, Holzmehl, Nussschalenmehl, Cellulosenpulver, Rückstände von Pflanzenextrakten, Aktivkohle usw., je für sich oder als Mischung untereinander in Frage. The active ingredients are mixed with solid carriers for the production of solid forms (dusts, grit). As carriers come z. B. kaolin, talc, bolus, loess, chalk, limestone, lime grit, attapulgite, dolomite, diatomaceous earth, precipitated silica, alkaline earth silicates, sodium and potassium aluminum silicates (feldspars and mica), calcium and magnesium sulfates, magnesium oxide, ground plastics, fertilizers such as fertilizers such as ammonium sulfate , Ammonium phosphate, ammonium nitrate, urea, ground vegetable products such as grain flour, tree bark flour, wood flour, nut shell flour, cellulose powder, residues of plant extracts, activated charcoal etc., each individually or as a mixture with one another. Die Korngrösse der Trägerstoffe beträgt für Stäubemit tel zweckmässig bis ca. 0,1 mm, für Streumittel ca. 0,075 bis 0,2 mm und für Granulate 0,2 mm oder mehr. The grain size of the carrier materials is expediently up to approx. 0.1 mm for dusts, approx. 0.075 to 0.2 mm for grit and 0.2 mm or more for granulates. Granulate lassen sich herstellen, indem man einen Wirkstoff der Formel I in einem organischen Lösungsmittel löst und die so erhaltene Lösung auf ein granuliertes Mineral, z. B. Attapulgit, SiO2, Granicalcium, Bentonit usw. aufbringt und dann das organische Lösungsmittel wieder verdampft. Granules can be produced by dissolving an active ingredient of the formula I in an organic solvent and applying the resulting solution to a granulated mineral, e.g. B. attapulgite, SiO2, granicalcium, bentonite, etc. applies and then the organic solvent evaporates again. In Wasser dispergierbare Wirkstoffkonzentrate, d. h. Active ingredient concentrates dispersible in water, d. H. Spritzpulver, Pasten und Emulsionskonzentrate stellen Mittel dar, die mit Wasser auf jede gewünschte Konzentration verdünnt werden können. Sie bestehen aus Wirkstoff, Trägerstoff, gegebenenfalls den Wirkstoff stabilisierenden Zusätzen, oberflächenaktiven Substanzen und Antischaummitteln und gegebenenfalls Lösungsmitteln. Wettable powders, pastes and emulsion concentrates are agents that can be diluted with water to any desired concentration. They consist of active ingredient, carrier, optionally additives stabilizing the active ingredient, surface-active substances and anti-foaming agents and optionally solvents. Die Wirkstoffkonzentration in diesen Mitteln beträgt 5% bis 80%. Spritzpulver und Pasten werden erhalten, indem man die Wirkstoffe mit Dispergiermitteln und pulverförmigen Trägerstoffen in geeigneten Vorrichtungen bis zur Homogenität vermischt und vermahlt. Als Trägerstoffe kommen beispielsweise die vorstehend für die festen Aufarbeitungsformen erwähnten in Frage. In manchen Fällen ist es vorteilhaft, Mischungen verschiedener Trägerstoffe zu verwenden. The active ingredient concentration in these agents is 5% to 80%. Wettable powders and pastes are obtained by mixing the active ingredients with dispersants and pulverulent carriers in suitable devices until homogeneous and grinding. Suitable carriers are, for example, those mentioned above for the solid work-up forms. In some cases it is advantageous to use mixtures of different carriers. Als Dispergatoren können beispielsweise verwendet werden: Kondensationsprodukte von sulfoniertem Naphthalin und sulfonierten Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäure mit Phenol und Formaldehyd sowie Alkali-, Ammonium- und Erdalkalisalze von Ligninsulfonsäure, weiter Alkylarylsulfonate, Alkali- und Erdalkalimetallsalze der Dibutylnaphthalinsulfonsäure, Fettalkoholsulfate, wie Salze sulfatierter Hexadecanole, Heptadecanole, Octadecanole und Salze von sulfatierten Fettalkoholglykoläthern, das Natriumsalz von Oleylmethyltaurid, ditertiäre Äthylenglykole, Dialkyldilaurylammoniumchlorid und fettsaure Alkali- und Erdalkalisalze. The following can be used as dispersants, for example: Condensation products of sulfonated naphthalene and sulfonated naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, and alkali metal, ammonium and alkaline earth metal salts of ligninsulfonic acid, further alkylarylsulfonates, alkali metal sulfonates, alkali metal sulfanolsulfonates, alkali metal sulfanolsulfonates, alkali metal sulfanate salts, hexadeceptyl sulfonic acid salts, hexadeceptyl sulfonates, alkali metal sulfonates, hexadeceptyl sulfonates, hexadeceptyl sulfonates , Octadecanols and salts of sulfated fatty alcohol glycol ethers, the sodium salt of oleyl methyl tauride, ditertiary ethylene glycols, dialkyldilaurylammonium chloride and fatty acid alkali and alkaline earth salts. Als Antischaummittel kommen zum Beispiel Siliconöle in Frage. Silicone oils, for example, can be used as antifoam agents. Die Wirkstoffe werden mit den oben aufgeführten Zusätzen so vermischt, vermahlen, gesiebt und passiert, dass bei den Spritzpulvern der feste Anteil eine Korngrösse von 0,02 bis 0,04 mm und bei den Pasten von 0,03 mm nicht überschrei tet. Zur Herstellung von Emulsionskonzentraten und Pasten werden Dispergiermittel, wie sie in den vorangehenden Abschnitten aufgeführt wurden, organische Lösungsmittel und Wasser verwendet. The active ingredients are mixed, ground, sieved and passed with the additives listed above in such a way that the solid portion of the wettable powders does not exceed a particle size of 0.02 to 0.04 mm and of the pastes of 0.03 mm. To produce emulsion concentrates and pastes, dispersants such as those listed in the previous sections, organic solvents and water are used. Der Gehalt an Wirkstoff in den oben beschriebenen Mitteln liegt zwischen 0,1 bis 95 /0. The content of active ingredient in the agents described above is between 0.1 and 95/0. Emulgierbare Konzentrate: Zur Herstellung eines 250/,eigen emulgierbaren Konzentrates werden folgende Stoffe verwendet: 5 Teile Wirkstoff 2,5 Teile epoxydiertes Pflanzenöl 10 Teile eines AlkylarylsulfonatlFettalkohol- polyglykoläther-Gemisches 5 Teile Dimethylformamid 57,5 Teile Xylol. Emulsifiable concentrates: The following substances are used to produce a 250 /, self-emulsifiable concentrate: 5 parts of active ingredient 2.5 parts of epoxidized vegetable oil 10 parts of an alkylarylsulfonate / fatty alcohol polyglycol ether mixture 5 parts of dimethylformamide, 57.5 parts of xylene. PATENTANSPRUCH I Verfahren zur Herstellung von heterocyclischen Carbonsäureaniliden der Formel I EMI15.1 worin Rl Cl-C4-Alkyl, Cl-C4-Alkoxy oder Halogen, R2 Wasserstoff, Ct-C3-Alkyl oder Halogen, R5 Wasserstoff, C1-C3-Alkyl oder Halogen, R5 Wasserstoff oder Methyl sind, wobei die Gesamtzahl von C-Atomen der Substituenten Rl, R2, R5 und R6 im Phenylring die Zahl 8 nicht übersteigt, EMI15.2 darstellen, wobei R', R" und R"' unabhängig voneinander Wasserstoff, Methyl oder Äthyl bedeuten und R4 einen unsubstituierten oder durch Methyl und/oder Halogen substituierten 5oder 6-gliedrigen heterocyclischen Rest mit 1 oder 2 Heteroatomen bedeutet, PATENT CLAIM I Process for the preparation of heterocyclic carboxylic acid anilides of the formula I. EMI15.1 wherein Rl is Cl-C4-alkyl, Cl-C4-alkoxy or halogen, R2 is hydrogen, Ct-C3-alkyl or halogen, R5 is hydrogen, C1-C3-alkyl or halogen, R5 is hydrogen or methyl, the total number of C- Atoms of the substituents Rl, R2, R5 and R6 in the phenyl ring does not exceed the number 8, EMI15.2 represent, where R ', R "and R"' are independently hydrogen, methyl or ethyl and R4 is an unsubstituted or substituted by methyl and / or halogen 5 or 6-membered heterocyclic radical with 1 or 2 heteroatoms, gekennzeichnet durch Überführung einer Verbindung der Formel II bei -20" bis +180 "C. EMI15.3 characterized by conversion of a compound of formula II at -20 "to +180" C. EMI15.3 mit Butyl-Lithium, Na-Hydrid oder K2CO3 in Pyridin oder Te with butyl lithium, sodium hydride or K2CO3 in pyridine or Te trahydrofuran in das Alkalisalz, welches dann mit dem Halo génessigsäure-Ester oder -Amid bzw. dem a-Halogenpropionsäure-Ester oder -Amid der Formel III Hal-X-R3 (III) weiter umgesetzt wird, wobei die Substituenten Rt bis R6 und X in den Formeln II und III die für Formel I gegebene Bedeutung haben, während Hal für ein Halogenatom steht. trahydrofuran into the alkali salt, which is then géacetic acid ester or amide with the halo or the α-halopropionic acid ester or amide of the formula III Hal-X-R3 (III) is reacted further, the substituents Rt to R6 and X in formulas II and III having the meaning given for formula I, while Hal stands for a halogen atom. UNTERANSPRÜCHE 1. Verfahren gemäss Patentanspruch 1, dadurch gekennzeichnet, dass die Reaktion bei 0 bis 120 "C durchgeführt wird. SUBCLAIMS 1. The method according to claim 1, characterized in that the reaction is carried out at 0 to 120 "C. 2. Verfahren gemäss Patentanspruch I, dadurch gekennzeichnet, dass die Reaktion in Anwesenheit eines weiteren Lösungsmittels durchgeführt wird. 2. The method according to claim I, characterized in that the reaction is carried out in the presence of a further solvent. 3. Verfahren gemäss Patentanspruch I, dadurch gekennzeichnet, dass Verbindungen der Formel I hergestellt werden, bei denen R4 den Furanrest bedeutet 4. Verfahren gemäss Patentanspruch I, dadurch gekennzeichnet, dass Verbindungen der Formel I hergestellt werden, bei denen R4 den Tetrahydrofuranrest bedeutet 5. Verfahren gemäss Patentanspruch I, dadurch gekennzeichnet, dass N-(1¯Methoxycarbonyl-äthyl)-N-(furan-(2" -carbonyl)-2,6-dimethylanilin hergestellt wird. 3. The method according to claim I, characterized in that compounds of the formula I are prepared in which R4 denotes the furan radical 4. The method according to claim I, characterized in that compounds of the formula I are prepared in which R4 denotes the tetrahydrofuran radical 5. The method according to claim I, characterized in that N- (1¯-methoxycarbonyl-ethyl) -N- (furan (2 "carbonyl) -2,6-dimethylaniline is produced. 6. Verfahren gemäss Patentanspruch I, dadurch gekennzeichnet, dass N(1'-Methoxycarbonyl-äthyl)-N < furan(2') -car bonylS2,3,6-trimethylanilin hergestellt wird. 6. The method according to claim I, characterized in that N (1'-methoxycarbonyl-ethyl) -N <furan (2 ') -carbonylS2,3,6-trimethylaniline is produced. 7. Verfahren gemäss Patentanspruch I, dadurch gekennzeichnet, dass N-(1'-Methoxyearbonyl-äthyl > N-furan- (2")car- bonylS2,6-dimethyl-3-bromanilin hergestellt wird. 7. The method according to claim I, characterized in that N- (1'-methoxy-carbonyl-ethyl> N-furan (2 ") carbonylS2,6-dimethyl-3-bromaniline is produced. 8. Verfahren gemäss Patentanspruch I, dadurch gekennzeichnet, dass N(1'-Methoxycarbonyl-äthyl)-N(furan- (2")-car bonylS2,4,6-trimethylanilin hergestellt wird. 8. The method according to claim I, characterized in that N (1'-methoxycarbonyl-ethyl) -N (furan- (2 ") - carbonylS2,4,6-trimethylaniline is produced. 9. Verfahren gemäss Patentanspruch I, dadurch gekennzeichnet, dass N-(1'-Methoxycarbonyl-äthylkN-(furan- (2")-carbonyl)-2,6-dimethyl4-chloranilin hergestellt wird. 9. The method according to claim I, characterized in that N- (1'-methoxycarbonyl-ethylkN- (furan- (2 ") - carbonyl) -2,6-dimethyl4-chloroaniline is produced. PATENTANSPRUCH II Die nach dem Verfahren gemäss Patentanspruch I herge stellten Verbindungen. PATENT CLAIM II The compounds produced by the method according to claim I. PATENTANSPRUCH III Verwendung der Verbindungen gemäss Patentanspruch II zur Herstellung von pflanzenfungiziden Mitteln. PATENT CLAIM III Use of the compounds according to claim II for the production of plant fungicidal agents.
CH1506177A 1974-04-02 1975-02-10 N-Furoyl-N-aryl-alanine esters CH606029A5 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH1506177A CH606029A5 (en) 1974-04-02 1975-02-10 N-Furoyl-N-aryl-alanine esters

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH457274A CH590608A5 (en) 1974-04-02 1974-04-02 N-Furoyl-N-aryl-alanine esters - prepd. e.g. by reacting N-aryl-alanine esters with 2-furoic acid or its derivs.
CH159175A CH603041A5 (en) 1974-04-02 1975-02-10 N-Furoyl-N-aryl-alanine esters
CH1506177A CH606029A5 (en) 1974-04-02 1975-02-10 N-Furoyl-N-aryl-alanine esters

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CH606029A5 true CH606029A5 (en) 1978-10-13

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CH1506177A CH606029A5 (en) 1974-04-02 1975-02-10 N-Furoyl-N-aryl-alanine esters

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2943019A1 (en) * 1978-10-27 1980-05-08 Ciba Geigy Ag MICROBICIDAL AGENT
DE3010412A1 (en) * 1979-03-21 1980-09-25 Ciba Geigy Ag PEST CONTROL
EP0019745A1 (en) * 1979-05-19 1980-12-10 BASF Aktiengesellschaft 2-Aminopropanal acetals, their preparation, fungicidal formulations containing them, their preparation and process for combating fungi
CN101805320A (en) * 2010-05-19 2010-08-18 江苏省激素研究所股份有限公司 Amide compounds and preparation method and applications thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2943019A1 (en) * 1978-10-27 1980-05-08 Ciba Geigy Ag MICROBICIDAL AGENT
DE3010412A1 (en) * 1979-03-21 1980-09-25 Ciba Geigy Ag PEST CONTROL
EP0019745A1 (en) * 1979-05-19 1980-12-10 BASF Aktiengesellschaft 2-Aminopropanal acetals, their preparation, fungicidal formulations containing them, their preparation and process for combating fungi
CN101805320A (en) * 2010-05-19 2010-08-18 江苏省激素研究所股份有限公司 Amide compounds and preparation method and applications thereof
CN101805320B (en) * 2010-05-19 2013-06-26 江苏省激素研究所股份有限公司 Amide compounds and preparation method and applications thereof

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