DE49071T1 - N-arylbenzamid-verbindungen. - Google Patents

N-arylbenzamid-verbindungen.

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Publication number
DE49071T1
DE49071T1 DE198181304225T DE81304225T DE49071T1 DE 49071 T1 DE49071 T1 DE 49071T1 DE 198181304225 T DE198181304225 T DE 198181304225T DE 81304225 T DE81304225 T DE 81304225T DE 49071 T1 DE49071 T1 DE 49071T1
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DE
Germany
Prior art keywords
formula
alkyl
hydrogen
arylbenzamide
derivative
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DE198181304225T
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English (en)
Inventor
Jr. Kenneth Wayne Indianapolis Indiana 46220 Burow
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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Filing date
Publication date
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of DE49071T1 publication Critical patent/DE49071T1/de
Pending legal-status Critical Current

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    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • A—HUMAN NECESSITIES
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    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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    • 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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • 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
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
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    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/04—Monocyclic monocarboxylic acids
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    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • C07D231/40—Acylated on said nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/88—Nitrogen atoms, e.g. allantoin
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
    • C07D237/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/14—Nitrogen atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
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    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Claims (5)

Gn ' '"' Veröffentlichung der Patentansprüche DE/EP O 049 071 T1 Europäische Patentanmeldung mit der Veröffentlichungs- Europäisches Aktenzeichen: 81 304 225.6 PATENTANS PRÜCHE 10· :
1. N-Arylbenzamidderivat der Formel I
worin
Z Sauerstoff oder Schwefel ist,
R1 Wasserstoff, Halogen, C1-C4-AIkYl oder C1-C4 ist,
R Wasserstoff, Halogen, C1-C.-Alkyl, C1-C.-Alkoxy,
or I 4r I 4t
C1~C4-Alkylthio oder Trifluormethyl ist,
R Wasserstoff, Halogen, C.-C.-Alkyl, C1-C4-AIkOXy oder C--C4~Alkylthio ist, mit den Maßgaben, daß einer oder beide der anderen Phenylsubstituenten
etwas anderes als Wasserstoff sind, falls einer
12 3 der Substituenten R , R oder R Alkyl ist und daß
einer oder beide der Substituenten R und R etwas
anderes als Wasserstoff sind, falls R Trifluormethyl ist, und
;
4
R eine Ary!gruppe ausgewählt aus .
OG':
N A . N
H K ist, worin
A für CH oder N und B für CH oder N steht,
mit der Maßgabe, daß eine der Brücken A und B für CH steht und die andere N ist,
X für NH, O oder S steht,
15
R für Wasserstoff oder C1-C.-Alkyl steht,
R für Wasserstoff,
1 oder 2
steht, worin
y eine Zahl von 0 bis 5 ist,
R , R und R unabhängig Wasserstoff, C--C. .,-Alkyl, Halogen-C.-C. .,-Alkyl, C0-C1 .,-Alkenyl, C0-C1-J-AIkInVl, C1-C.-AIkOXy-C1-Cg-Alkyl, C1-C^Alkylthio-
ν— λ W /- t\. XJS-J^ _L f k^ λ d rtXAyÄy ρ ^-· ο ^* λ .γ* J. λ. α.
I O I Jo^ ; 1' '; .;: - : ; . Z : ft '■■;
noyloxy-C^Cg-Alkyl, C^Cg-Alkylthio
^- "" Jjl!:"'1^!:';il -r-j'-iv.,·^!,· vH av τ oder 2
./ ,^CH^^O^CH^^, oder _.(CH.)
sind, Worin''
·. O
m eine Zahl von 0 bis 4 ist,
η für 0 oder 1 steht und .
9 10
R und R unabhängig Wasserstoff, Halogen,
C^C.-Alkyl oder C2-C4-Alkenyl sind,
1 2
Q und Q unabhängig CH3, O, S, CH3O oder CH9S sind, mit der Maßgabe, daß y nicht 0
1 2 ist, falls Q und Q beide etwas anderes
als CH9 sind,
mit der Maßgabe, daß R nur dann Wasserstoff ist, falls R4 für
2 3
steht, und mit der weiteren Maßgabe, daß R und R etwas
4 anderes als Wasserstoff sind, falls R für
β _ . N—
_jL 4Ur5 oder -4- 4--ίΓ
R u
steht, n
oder ein landwirtschaftlich annehmbares Salz hiervon.
2. N-Arylbenzamidderivat der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, daß
' ■ " ■-..'..-■■ Z Sauerstoff ist,
4 ■ ■ ■■■·-.■■■ ■. ■.
R eine Ary!gruppe ausgewählt aus
>-
ist, worin R Wasserstoff ist und RJ Wasserstoff,
oder ^1 _1C
'R M oder 2 ist, worin
R und R unabhängig Wasserstoff, C.-C.-Alkyl, C2-C4-Alkenyl oder C2-C4-Alkinyl sind,
y eine Zahl von 0 bis 4 ist,
R Wasserstoff, C.-C.3-Alkyl, HaIOgCn-C1-C. 3-AI-kyl, C3-C13-Alkenyl/ C3-C13~Alkinyl, C1-C4-
AIkOXy-C1-Cg-Alkyl, C1-C4~Alkylthio-C1-C5-Alkyl,
X.
oder 2
R
ist, worin
m eine Zahl von 0 bis 4 ist,
η für O oder 1 steht und
9 10
R und R unabhängig Wasserstoff, Halogen, C1
C4~Alkyl oder C2-C4~Alkenyl sind.
— 5 — 1
3. N-Arylbenzamidderivat der Formel (I) gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, daß Z Sauerstoff ist und
4 R für
■ I—ι
• —κ ;·—R3 oder —«k
steht.
4. N-Arylbenzamidderivat der Formel (I) gemäß einem der
Ansrüche 1 bis 3, dadurch gekennzeichnet, daß R Wasser-
2
stoff ist und R und R für C1-C4-AIkOXy stehen.
5. N-Arylbenzamidderivat der Formel (I) gemäß Anspruch
4, dadurch gekennzeichnet, daß R für 2-Methoxy steht und R ein 6-Methoxysubstituent ist.
6. N-Arylbenzamidderivat der Formel (I) gemäß einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, daß R e sterisch gehinderte oder voluminöse Gruppe ist.
7. N-Arylbenzamidderivat der Formel (I) gemäß Anspruch 6, dadurch gekennzeichnet, daß R eine Gruppe der Formel
ΐ , ■ -
6 "7
ist, worin R Wasserstoff oder Cj-C.-Alkyl ist, R für
steht und R8 für C^C^-Alkyl steht.
8. N-Arylbenzamidderivat der Formel (I) gemäß Anspruch 7, dadurch ge]
propyl steht.
7, dadurch gekennzeichnet, daß R für 1-Ethyl-1-methyl-
9. N-Arylbenzamidderivat der Formel (I) gemäß Anspruch 6, dadurch gekennzeichnet, daß R eine Gruppe der Formel
/a)
^K ; 1 oder 2
ist, worin R für C1-C.-Alkyl steht, R und R unabhän
12 . 15 gig Wasserstoff oder Cj-C^-Alkyl sind, Q und Q für CH stehen und y eine Zahl von 0 bis 4 ist.
10. N-Arylbenzamidderivat der Formel (I) gemäß Anspruch 9, dadurch
cyclohexyl steht.
spruch 9, dadurch gekennzeichnet, daß R für 1-Ethyl-
11. N-/3- Cl-Ethyl-1-methylpropyl)-5-isoxazoly1/-2,6-dimethoxybenzamid.
12. N-/3-(1 ,1-Dimethylethyl)-S-isoxazolyV-2,6-dimethoxybenzamid.
1 3. H-/3- (1 -Ethylcyclohexyl) -5-isoxazolyl./-2 ,6-dimethoxybenzamid.
30
14. N-£6-(1,1-Dimethylethyl)pyridazin-3-yl/-2,6-dimethoxybenzam.id.
1 5 . N-/_6- (1 -Ethyl-1-methylpropyl) pyridazin-S-yV-2 , 6-dimethoxybenzamid*
O P
16. Verwendung eines N-Arylbenzamidderivats der Formel (I) oder eines landwirtschaftlich annehmbaren Salzes hiervon gemäß einem der Ansprüche 1 bis 15 als Herbizid.
17. Herbizide Formulierung, dadurch gekennzeichnet, daß sie ein N-Arylbenzamidderivat der Formel (I) oder ein landwirtschaftlich annehmbares Salz hiervon gemäß einem der Ansprüche 1 bis 15 als Wirkstoff in Verbindung mit einem oder mehreren landwirtschaftlich annehmbaren Trägern oder Verdünnungsmitteln hierfür enthält.
18. Herbizide Formulierung nach Anspruch 17, dadurch gekennzeichnet, daß sie ein benetzbares Pulver ist.
19. Verfahren zur Bekämpfung des Wachstums einer uner- , wünschten Vegetation, dadurch gekennzeichnet, daß man die Stelle, wo man eine Vegetation bekämpfen möchte, mit einer herbizid wirksamen Menge eines N-Arylbenzamidderivats der Formel (I) oder eines landwirtschaftlich annehmbares Salzes hiervon gemäß einem der Ansprüche 1 bis 15 behandelt.
20. Verfahren zur Herstellung eines N-Arylbenzamidderivats der Formel (I) gemäß einem der Ansprüche 1 bis 15, dadurch gekennzeichnet, daß man
Ca) ein Amin der Formel
30
mit einem substituierten Benzoesäurederivat der Formel
35
0 0 /;. " Μ
worin L eine Abgangsgruppe ist, acyliert und so ein N-Arylbenzamidderivat der Formel (I) bildet, worin Z für Sauerstoff steht, 5
(b) das Produkt der Umsetzung (a) gegebenenfalls
thioniert und so ein N-Arylbenzamid der Formel (I) bildet, worin Z für Schwefel steht, und
(c) ein gemäß Umsetzung (a) oder (b) hergestelltes N-Arylbenzamidderivat der Formel (I) gegebenenfalls in ein Salz überführt und so ein landwirtschaftlich annehmbares Salz bildet.
DE198181304225T 1980-09-16 1981-09-15 N-arylbenzamid-verbindungen. Pending DE49071T1 (de)

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