DE3939892A1 - New triazolo-(4,3-a)pyridine(s) and N'-(2-pyridyl)-hydrazone(s) - Google Patents

New triazolo-(4,3-a)pyridine(s) and N'-(2-pyridyl)-hydrazone(s)

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Publication number
DE3939892A1
DE3939892A1 DE19893939892 DE3939892A DE3939892A1 DE 3939892 A1 DE3939892 A1 DE 3939892A1 DE 19893939892 DE19893939892 DE 19893939892 DE 3939892 A DE3939892 A DE 3939892A DE 3939892 A1 DE3939892 A1 DE 3939892A1
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Germany
Prior art keywords
halogen
alkyl
alkoxy
phenyl
alkylamino
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.)
Withdrawn
Application number
DE19893939892
Other languages
German (de)
Inventor
Jens Dipl Chem Dr Geisler
Helga Dipl Chem Dr Franke
Alfred Dipl Chem Dr Angermann
Guenter Dipl Chem D Hoemberger
Gerhard Johann
Richard Dipl Biol Dr Rees
Juergen Bohner
Ruediger Dipl Biol Dr Mertens
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Bayer Pharma AG
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Schering AG
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Publication date
Application filed by Schering AG filed Critical Schering AG
Priority to DE19893939892 priority Critical patent/DE3939892A1/en
Priority to IL96432A priority patent/IL96432A0/en
Priority to JP2323362A priority patent/JPH03181463A/en
Priority to PT96034A priority patent/PT96034A/en
Priority to BR909006067A priority patent/BR9006067A/en
Priority to KR1019900019667A priority patent/KR910009155A/en
Priority to EP19900250296 priority patent/EP0430385A3/en
Priority to CN90109686A priority patent/CN1052238A/en
Publication of DE3939892A1 publication Critical patent/DE3939892A1/en
Withdrawn legal-status Critical Current

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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
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C07D213/77—Hydrazine radicals
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Abstract

Substd. 1,2,4-triazolo-(4,3-a)pyridines of formula (I) and substd. N'-(2-pyridyl)hydrazones of formula (II) for use in herbicidal compositions are new, where A = 5-membered heterocycle (comprising 1-3 of N, O or S; ring C's opt. substd. with halo, 1-4C alkyl or halo (1-4C)alkyl and 1 ring N is opt. substd. with 1-4C alkyl), 1-10C alkyl (opt. substd. with B), 2-10C alkenyl (opt. substd. with B, or 2-10C alkynyl (opt. substd. with B); B = halo, Cn, 3-6C cycloalkyl, halo-(3-6C)cycloalkyl, cyano-(3-6C)cycloalkyl, 1-4C alkyl-3-6C cycloalkyl, halo(1-4C)alkyl-(3-6C) cycloalkenyl, halo(1-4C)alkyl (3-6C)cycloalkenyl, cyano (1-4C)alkyl (3-6C)cycloalkenyl (i), 3-8C cycloalkyl (ii) or 3-8C cycloalkenyl; (iii); (i), (ii) and (iii) are opt. substd. with halo, CN, 1-4C alkyl, halo(1-4C)alkyl, cyano (1-4C)alkyl, 2-4C alkenyl, halo(2-4C)alkenyl, cyano(2-4C)alkenyl, 2-4C alkynyl, halo(2-4C)alkynyl, cyano(2-4C)alkynyl (iv), Ph(v) or benzyl (vi); R1 = halo, Oh, 1-6C alkyl, halo (1-6C)alkyl, 1-6C alkoxy, halo (1-6C)alkoxy, 1-6C alkylthio, halo(1-6C)alkylthio, 1-6C alkylsulphinyl, 1-6C alkylsulphonyl, 1-6C alkoxy; carbonyl, phenyl (1-6C) alkoxycarbonyl, Ph, phenoxy.

Description

Die Erfindung betrifft die Verwendung von teilweise bekannten substituier­ ten 1,2,4-Triazolo[4,3-a]pyridinen als Mittel mit herbizider Wirkung.The invention relates to the use of partially known substitutes ten 1,2,4-triazolo [4,3-a] pyridines as herbicidal agents.

Es ist bekannt, daß bestimmte 1,2,4-Triazolo[4,3-a]pyridine, die in 3-Stel­ lung mit einer Phenylgruppe substituiert sind, pharmakologische Eigenschaften besitzen (EP-Anmeldung 02 10 648). Über eine herbizide Wirkung dieser Verbindungsklasse ist bisher nichts bekannt.It is known that certain 1,2,4-triazolo [4,3-a] pyridines, which are in 3-st are substituted with a phenyl group, pharmacological properties own (EP application 02 10 648). About a herbicidal effect of this No connection class is known yet.

Es wurde gefunden, daß Mittel enthaltend teilweise bekannte substituierte 1,2,4-Triazolo[4,3-a]pyridine der allgemeinen Formel IIt has been found that compositions containing partially known substituted ones 1,2,4-triazolo [4,3-a] pyridines of the general formula I

in der
R¹ einen Phenylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₃-C₆-Cycloal­ kyl, Halogen-C₃-C₆-cycloalkyl, Phenyl-C₁-C₆-alkyl, C₂-C₆-Alkenyl, Halo­ gen-C₂-C₆-alkenyl, Phenyl-C₂-C₆-alkenyl, C₂-C₆-Alkinyl, Halogen-C₂-C₆- alkinyl, Phenyl-C₂-C₆-alkinyl, C₁-C₆-Alkoxy, Halogen-C₁-C₆-alkoxy, C₁- C₄-Alkoxy-C₁-C₆-alkoxy, C₁-C₄-Alkylamino-C₁-C₆-alkoxy, Di-C₁-C₄-alkyl­ amino-C₁-C₆-alkoxy, C₂-C₆-Alkenyloxy, Mercapto, C₁-C₆-Alkylthio, Halo­ gen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkyl­ carbonyl, Halogen-C₁-C₆-alkylcarbonyl, C₁-C₆-Alkoxycarbonyl, Phenyl, Halogenphenyl, C₁-C₆-Alkylphenyl, Phenoxy, Halogenphenoxy, C₁-C₆-Alkyl­ phenoxy, Nitrophenoxy, Amino, C₁-C₄-Alkylamino, Di-.C₁-C₄-alkylamino, Phenylamino, Halogenphenylamino, C₁-C₆-Alkylphenylamino, Cyano, Nitro, Methylendioxy, Ethylidendioxy oder Isopropylidendioxy substituierten Phenylrest, einen Naphthylrest oder einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Hydroxy, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, Ami­ no, C₁-C₄-Alkylamino, Di-C₁-C₄-alkylamino, Cyano oder Nitro substituierten Naphthylrest,
R² Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆-Alkoxy, Halo­ gen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkyl­ sulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl-C₁-C₆-alkoxy­ carbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁-C₄-alkylamino, Cyano oder Nitro,
R³ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁- C₄-alkylamino, Cyano oder Nitro,
R⁴ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, Amino, C₁-C₄-Alkylamino, Di-C₁- C₄-alkylamino, Cyano oder Nitro,
R⁵ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁- C₄-alkylamino, Cyano oder Nitro und
n 0 oder 1
bedeuten, überraschenderweise eine ausgeprägte herbizide Wirkung besitzen.in the
R¹ is a phenyl radical, one or more, the same or different, by halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₃-C₆-cycloalyl, halogen-C₃-C₆-cycloalkyl, phenyl-C₁ -C₆-alkyl, C₂-C₆-alkenyl, halo gene-C₂-C₆-alkenyl, phenyl-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halogen-C₂-C₆-alkynyl, phenyl-C₂-C₆-alkynyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₆-alkoxy, C₁-C₄-alkylamino-C₁-C₆-alkoxy, di-C₁-C₄-alkyl amino-C₁-C₆ -alkoxy, C₂-C₆-alkenyloxy, mercapto, C₁-C₆-alkylthio, halo gene-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkyl carbonyl, halogen-C₁-C₆ -alkylcarbonyl, C₁-C₆-alkoxycarbonyl, phenyl, halophenyl, C₁-C₆-alkylphenyl, phenoxy, halophenoxy, C₁-C₆-alkyl phenoxy, nitrophenoxy, amino, C₁-C₄-alkylamino, di-.C₁-C₄-alkylamino, phenylamino , Halogenphenylamino, C₁-C₆-alkylphenylamino, cyano, nitro, methylenedioxy, ethyl lidendioxy or isopropylidenedioxy substituted phenyl, a naphthyl or one or more, the same or different, by halogen, hydroxy, C₁-C₄-alkyl, C₁-C₄-alkoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄- alkylamino, cyano or nitro substituted naphthyl,
R² halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁- C₆-alkyl sulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl-C₁-C₆-alkoxy carbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano or nitro,
R³ is hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl- C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁- C₄-alkylamino, cyano or nitro,
R⁴ hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl- C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano or nitro ,
R⁵ hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl-C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano or nitro and
n 0 or 1
mean, surprisingly have a pronounced herbicidal action.

Die Bezeichnung "Halogen" umfaßt Fluor, Chlor, Brom und Jod.The term "halogen" includes fluorine, chlorine, bromine and iodine.

"Halogenalkyl", "Halogenalkoxy" oder "Halogenalkylthio" bedeutet, daß ein oder mehrere Wasserstoffatome durch Fluor, Chlor, Brom oder Jod ersetzt sind."Haloalkyl", "haloalkoxy" or "haloalkylthio" means that a or several hydrogen atoms are replaced by fluorine, chlorine, bromine or iodine are.

Unter den Begriffen "Alkyl", "Alkenyl" und "Alkinyl" sind sowohl geradkettige als auch verzweigte Kohlenwasserstoffreste zu verstehen.The terms "alkyl", "alkenyl" and "alkynyl" are both straight chain to understand as well as branched hydrocarbon residues.

Die erfindungsgemäß verwendbaren substituierten 1,2,4-Triazolo[4,3-a]pyri­ dine der allgemeinen Formel I sind teilweise bekannt (Bull. Chem. Soc. Japan 53 (1980) 2007-2011, Khim. Geterotsikl. Soedin. 6 (1974) 792-795, Croat. Chem. Acta 49 (1977) 135-140).The substituted 1,2,4-triazolo [4,3-a] pyri which can be used according to the invention Some of the general formula I are known (Bull. Chem. Soc.  Japan 53 (1980) 2007-2011, Khim. Heterotics Soedin. 6 (1974) 792-795, Croat. Chem. Acta 49 (1977) 135-140).

Noch nicht bekannt sind jedoch die substituierten 1,2,4-Triazolo[4,3-a]pyridine der allgemeinen Formel IaHowever, the substituted 1,2,4-triazolo [4,3-a] pyridines are not yet known of the general formula Ia

in der
R¹* einen Phenylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl, Phenyl-C₁-C₆-alkyl, C₂-C₆-Alkenyl, Halogen- C₂-C₆-alkenyl, Phenyl-C₂-C₆-alkenyl, C₂-C₆-Alkinyl, Halogen-C₂-C₆- alkinyl, Phenyl-C₂-C₆-alkinyl, C₁-C₆-Alkoxy, Halogen-C₁-C₆-alkoxy, C₁- C₄-Alkoxy-C₁-C₆-alkoxy, C₁-C₄-Alkylamino-C₁-C₆-alkoxy, Di-C₁-C₄-alkyl­ amino-C₁-C₆-alkoxy, C₂-C₆-Alkenyloxy, Mercapto, C₁-C₆-Alkylthio, Halogen- C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Al­ kylcarbonyl, Halogen-C₁-C₆-alkylcarbonyl, C₁-C₆-Alkoxycarbonyl, Phenyl, Halogenphenyl, C₁-C₆-Alkylphenyl, Phenoxy, Halogenphenoxy, C₁-C₆-Alkyl­ phenoxy, Nitrophenoxy, Amino, C₁-C₄-Alkylamino. Di-C₁-C₄-alkylamino, Phenylamino, Halogenphenylamino, C₁-C₆-Alkylphenylamino, Cyano, Nitro, Methylendioxy, Ethylidendioxy oder Isopropylidendioxy substituierten Phenylrest, einen Naphthylrest oder einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Hydroxy, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, Amino, C₁-C₄-Alkylamino, Di-C₁-C₄-alkylamino, Cyano oder Nitro substituierten Naphthylrest,
R²* Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆-Alkoxy, Halo­ gen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkyl­ sulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl-C₁-C₆-alkoxy­ carbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁-C₄-alkylamino, Cyano oder Nitro, mit der Einschränkung, daß R²* nicht Brom oder Methyl ist, wenn R¹* Phenyl und n* 0 ist, und R²* nicht Nitro ist, wenn R¹* 4-Methoxyphenyl und n* 0 ist.
R³ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁- C₄-alkylamino, Cyano oder Nitro,
R⁴ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Ci-C₁- C₄-alkylamino, Cyano oder Nitro,
R⁵ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁-C₄- alkylamino, Cyano oder Nitro und
n* 0 oder 1
bedeuten.in the
R¹ * is a phenyl radical, one or more, the same or different, by halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, phenyl-C₁ -C₆-alkyl, C₂-C₆-alkenyl, halogen- C₂-C₆-alkenyl, phenyl-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halogen-C₂-C₆-alkynyl, phenyl-C₂-C₆-alkynyl, C₁ -C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁- C₄-alkoxy-C₁-C₆-alkoxy, C₁-C₄-alkylamino-C₁-C₆-alkoxy, di-C₁-C₄-alkyl amino-C₁-C₆- alkoxy, C₂-C₆-alkenyloxy, mercapto, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylcarbonyl, halogen-C₁-C₆-alkylcarbonyl , C₁-C₆-alkoxycarbonyl, phenyl, halophenyl, C₁-C₆-alkylphenyl, phenoxy, halophenoxy, C₁-C₆-alkyl phenoxy, nitrophenoxy, amino, C₁-C₄-alkylamino. Di-C₁-C₄-alkylamino, phenylamino, halophenylamino, C₁-C₆-alkylphenylamino, cyano, nitro, methylenedioxy, ethylidendioxy or isopropylidendioxy substituted phenyl radical, a naphthyl radical or a one or more, identical or different, halogen or hydroxy, C₁-C₄ -Alkyl, C₁-C₄-alkoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano or nitro substituted naphthyl,
R² * halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkyl sulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl-C₁-C₆-alkoxy carbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano or nitro , with the restriction that R² * is not bromine or methyl when R¹ * is phenyl and n * 0, and R² * is not nitro when R¹ * is 4-methoxyphenyl and n * 0.
R³ is hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl- C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁- C₄-alkylamino, cyano or nitro,
R⁴ hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl- C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, Ci-C₁- C₄-alkylamino, cyano or nitro,
R⁵ hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl-C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano or nitro and
n * 0 or 1
mean.

Die Herstellung der noch nicht bekannten substituierten 1,2,4-Triazolo [4,3-a]pyridine läßt sich in Anlehnung an bekannte Methoden durchführen (zum Beispiel J. Org. Chem. 31 (1966) 251, Chem. Ber. 103 (1970) 1918), indem manThe preparation of the not yet known substituted 1,2,4-triazolo [4,3-a] pyridine can be carried out based on known methods (e.g. J. Org. Chem. 31 (1966) 251, Chem. Ber. 103 (1970) 1918) by one

  • A) eine Verbindung der allgemeinen Formel II in der R¹*, R²*, R³, R⁴, R⁵ und n* die unter der allgemeinen Formel Ia angegebenen Bedeutungen haben, mit einem Halogenierungsmittel umsetzt oder A) a compound of general formula II in which R¹ *, R² *, R³, R⁴, R⁵ and n * have the meanings given under the general formula Ia, reacted with a halogenating agent or
  • B) eine Verbindung der allgemeinen Formel III in der R¹*, R²*, R³*, R⁴, und R⁵ und n* die unter der allgemeinen Formel Ia angegebenen Bedeutungen haben, mit einem Oxydationsmittel zur Reaktion bringt.B) a compound of the general formula III in which R¹ *, R² *, R³ *, R⁴, and R⁵ and n * have the meanings given under the general formula Ia, reacting with an oxidizing agent.

Als Halogenierungsmittel für die Verfahrensvariante A) haben sich Phosphor­ oxychlorid und Thionylchlorid als besonders vorteilhaft erwiesen.Phosphorus has been used as halogenating agent for process variant A) oxychloride and thionyl chloride have proven to be particularly advantageous.

Als Oxydationsmittel für die Verfahrensvariante B) sind Bleitetraacetat und Brom besonders geeignet.Lead tetraacetate and are as oxidizing agents for process variant B) Bromine particularly suitable.

Die Herstellungsmethoden A) und B) können mit oder ohne Lösungsmittel durchgeführt werden, wobei im Bedarfsfall solche Lösungs- beziehungsweise Verdünnungsmittel zum Einsatz kommen, die gegenüber den jeweiligen Reaktanden inert sind. Beispielsweise für solche Lösungsmittel beziehungsweise Verdün­ nungsmittel sind aliphatische, alicyclische und aromatische Kohlenwasser­ stoffe, die jeweils gegebenenfalls chloriert sein können, wie zum Beispiel Hexan, Cyclohexan, Petrolether, Ligroin, Benzol, Toluol, Xylol, Methylen­ chlorid, Chloroform, Kohlenstofftetrachlorid, Ethylenchlorid, Trichlorethylen und Chlorbenzol, Ether, wie zum Beispiel Diethylether, Methylethylether, Methyl-t-butylether, Diisopropylether, Dibutylether, Dioxan und Tetra­ hydrofuran, Ketone, wie zum Beispiel Aceton, Methylethylketon, Methyl­ isopropylketon und Methylisobutylketon, Nitrile, wie zum Beispiel Acetonitril und Propionitril, Alkohole, wie zum Beispiel Methanol, Ethanol, Iso­ propanol, Butanol, tert.-Butanol, tert.-Amylalkohol und Ethylenglycol, Ester, wie zum Beispiel Ethylacetat und Amylacetat, Säureamide, wie zum Beispiel Dimethylformamid und Dimethylacetamid, Sulfoxide, wie zum Beispiel Dimethylsulfoxid, und Sulfone, wie zum Beispiel Sulfolan, sowie Basen, wie zum Beispiel Pyridin und Triethylamin. The production methods A) and B) can with or without solvent be carried out, if necessary, such solution or Diluents are used, which are compared to the respective reactants are inert. For example for such solvents or diluents Means are aliphatic, alicyclic and aromatic hydrocarbons substances that may or may not be chlorinated, such as Hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichlorethylene and chlorobenzene, ethers, such as, for example, diethyl ether, methyl ethyl ether, Methyl t-butyl ether, diisopropyl ether, dibutyl ether, dioxane and tetra hydrofuran, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile and propionitrile, alcohols, such as, for example, methanol, ethanol, iso propanol, butanol, tert-butanol, tert-amyl alcohol and ethylene glycol, Esters such as ethyl acetate and amyl acetate, acid amides such as Example dimethylformamide and dimethylacetamide, sulfoxides such as Dimethyl sulfoxide, and sulfones, such as sulfolane, and bases, such as for example pyridine and triethylamine.  

Alle Reaktionen werden vorzugsweise unter dem Druck der Umgebung durchge­ führt, wenngleich sie auch bei erhöhtem oder vermindertem Druck ausgeführt werden könnten. Sie können ferner innerhalb eines breiten Temperaturbereichs durchgeführt werden. Im allgemeinen werden sie bei einer Temperatur zwischen -20°C und 200°C durchgeführt.All reactions are preferably carried out under the pressure of the environment leads, although it is carried out at elevated or reduced pressure could become. They can also operate within a wide temperature range be performed. Generally, they are at a temperature between -20 ° C and 200 ° C.

Die nach den oben genannten Verfahren hergestellten erfindungsgemäßen Ver­ bindungen können nach den üblichen Methoden aus dem Reaktionsgemisch isoliert werden, beispielsweise durch Abdestillieren des eingesetzten Lösungsmittels bei normalem oder vermindertem Druck, durch Ausfällen mit Wasser oder durch Extraktion. Ein erhöhter Reinheitsgrad kann in der Regel durch säulenchromatographische Aufreinigung sowie durch fraktionierte Destillation oder Kristallisation erhalten werden.The Ver according to the invention produced by the above-mentioned processes Bonds can be isolated from the reaction mixture by the usual methods be, for example by distilling off the solvent used at normal or reduced pressure, through precipitation with water or by extraction. An increased degree of purity can usually be caused by purification by column chromatography and by fractional distillation or crystallization can be obtained.

Die erfindungsgemäßen Verbindungen stellen in der Regel fast farb- und ge­ ruchlose Flüssigkeiten oder Kristalle dar, die schwerlöslich in Wasser, bedingt löslich in aliphatischen Kohlenwasserstoffen, wie Petrolether, Hexan, Pentan und Cyclohexan, gut löslich in halogenierten Kohlenwasserstoffen, wie Chloroform, Methylenchlorid und Tetrachlorkohlenstoff, aromatischen Kohlenwasserstoffen, wie Benzol, Toluol und Xylol, Ethern, wie Diethylether, Tetrahydrofuran und Dioxan, Carbonsäurenitrilen, wie Acetonitril, Alkoholen, wie Methanol und Ethanol, Carbonsäureamiden, wie Dimethylformamid, und Sulfoxiden, wie Dimethylsulfoxid, sind.The compounds of the invention are usually almost colored and ge nondescript liquids or crystals that are poorly soluble in water soluble in aliphatic hydrocarbons, such as petroleum ether, hexane, Pentane and cyclohexane, readily soluble in halogenated hydrocarbons, such as chloroform, methylene chloride and carbon tetrachloride, aromatic Hydrocarbons such as benzene, toluene and xylene, ethers such as diethyl ether, Tetrahydrofuran and dioxane, carbonitriles, such as acetonitrile, Alcohols, such as methanol and ethanol, carboxamides, such as dimethylformamide, and sulfoxides such as dimethyl sulfoxide.

Die bei dem Herstellungsverfahren A) benötigten Hydrazide der allgemeinen Formel II sowie die im Herstellungsverfahren B) einzusetzenden Hydrazone der allgemeinen Formel III sind entweder literaturbekannt oder können in Anlehnung an literaturbekannte Methoden hergestellt werden. Einschlägige Techniken sind beispielsweise in J. Chem. Soc. 1955, 688 oder J. Chem. Soc. 1957, 727 beschrieben.The hydrazides of general preparation required in production process A) Formula II and the hydrazones to be used in production process B) of the general formula III are either known from the literature or can be found in Based on methods known from the literature. Relevant Techniques are described, for example, in J. Chem. Soc. 1955, 688 or J. Chem. Soc. 1957, 727.

Die erfindungsgemäßen Verbindungen zeigen eine gute herbizide Wirkung bei breitblättrigen Unkräutern und Gräsern. Ein selektiver Einsatz der erfin­ dungsgemäßen Wirkstoffe ist in verschiedenen Kulturen möglich, zum Beispiel in Raps, Rüben, Sojabohnen, Baumwolle, Reis, Gerste, Weizen und anderen Ge­ treidearten. Dabei sind einzelne Wirkstoffe als Selektivherbizide in Rüben, Baumwolle, Soja und Getreide besonders geeignet. Ebenso können die Verbindungen zur Unkrautbekämpfung in Dauerkulturen, wie zum Beispiel Forst-, Ziergehölz-, Obst-, Wein-, Citrus-, Nuß-, Bananen-, Kaffee-, Tee-, Gummi-, Ölpalm-, Kakao-, Beerenfrucht- und Hopfenanlagen, und zur selektiven Un­ krautbekämpfung in einjährigen Kulturen eingesetzt werden.The compounds according to the invention show a good herbicidal activity broad-leaved weeds and grasses. A selective use of the inventions Active substances according to the invention are possible in different cultures, for example in rapeseed, beets, soybeans, cotton, rice, barley, wheat and other Ge cereals. Individual active ingredients are selective herbicides in beets,  Cotton, soybeans and cereals are particularly suitable. Likewise, the connections for weed control in permanent crops, such as forestry, Ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, Oil palm, cocoa, berry fruit and hop plants, and for selective un herb control can be used in annual crops.

Die erfindungsgemäßen Verbindungen können zum Beispiel bei den folgenden Pflanzengattungen verwendet werden:The compounds of the present invention can include, for example, the following Plant genera are used:

Dikotyle Unkräuter der Gattungen Sinapis, Lepidium, Galium, Stellaria, Ma­ tricaria, Anthemis, Galinsoga, Chenopodium, Brassica, Urtica, Senecio, Ama­ ranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Lamium, Veronica, Abutilon, Datura, Viola, Galeopsis, Papaver, Centaurea und Chrysanthemum.Dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Ma tricaria, anthemis, galinsoga, chenopodium, brassica, urtica, senecio, ama ranthus, portulaca, xanthium, convolvulus, ipomoea, polygonum, sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Lamium, Veronica, Abutilon, Datura, Viola, Galeopsis, Papaver, Centaurea and Chrysanthemum.

Monokotyle Unkräuter der Gattungen Avena, Alopecurus, Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron, Sagittaria, Monochoria, Fimbristylis, Eleocharis, Ischaemum und Apera.Monocot weeds of the genera Avena, Alopecurus, Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron, Sagittaria, Monochoria, Fimbristylis, Eleocharis, Ischaemum and Apera.

Die Aufwandmengen schwanken je nach Anwendungsart im Vor- und Nachauflauf in Grenzen zwischen 0,001 bis 5 kg/ha.Depending on the type of application, the application rates fluctuate in the pre- and post-emergence between 0.001 and 5 kg / ha.

Die erfindungsgemäßen Wirkstoffe können auch als Defoliant, Desiccant und als Krautabtötungsmittel verwendet werden.The active compounds according to the invention can also be used as defoliants, desiccants and can be used as an herbicide.

Die erfindungsgemäßen Verbindungen können entweder allein, in Mischung mit­ einander oder mit anderen Wirkstoffen angewendet werden. Gegebenenfalls können andere Pflanzenschutz- oder Schädlingsbekämpfungsmittel je nach dem gewünschten Zweck zugesetzt werden. Sofern eine Verbreiterung des Wirkungs­ spektrums beabsichtigt ist, können auch andere Herbizide zugesetzt werden.The compounds according to the invention can either be used alone or in a mixture with each other or with other active substances. Possibly other pesticides or pesticides may vary depending on the desired purpose can be added. Unless there is a broadening of the impact other herbicides can be added.

Beispielsweise eignen sich als herbizid wirksame Mischungspartner diejenigen Wirkstoffe, die in Weed Abstracts, Vol. 38, No. 3, 1989, unter dem Titel "List of common names and abbreviations employed for currently used herbicides and plant growth regulators in Weed Abstracts" aufgeführt sind. For example, those suitable as herbicidally active mixture partners Active ingredients described in Weed Abstracts, Vol. 38, No. 3, 1989, under the title "List of common names and abbreviations employed for currently used herbicides and plant growth regulators in Weed Abstracts ".  

Eine Förderung der Wirkintensität und der Wirkungsgeschwindigkeit kann zum Beispiel durch wirkungssteigernde Zusätze, wie organische Lösungsmittel, Netzmittel und Öle, erzielt werden. Solche Zusätze lassen daher gegebenen­ falls eine Verringerung der Wirkstoffdosierung zu.A promotion of the intensity and speed of action can Example by adding additives, such as organic solvents, Wetting agents and oils can be achieved. Such additives are therefore given if a decrease in drug dosage.

Zweckmäßig werden die gekennzeichneten Wirkstoffe oder deren Mischungen in Form von Zubereitungen wie Pulvern, Streumitteln, Granulaten, Lösungen, Emulsionen oder Suspensionen, unter Zusatz von flüssigen und/oder festen Trägerstoffen beziehungsweise Verdünnungsmitteln und gegebenenfalls Haft-, Netz-, Emulgier- und/oder Dispergierhilfsmitteln angewandt.The labeled active ingredients or their mixtures are expediently in Form of preparations such as powders, sprinkling agents, granules, solutions, Emulsions or suspensions, with the addition of liquid and / or solid Carriers or diluents and, if necessary, adhesives, Wetting, emulsifying and / or dispersing aids applied.

Geeignete flüssige Trägerstoffe sind zum Beispiel aliphatische und aromatische Kohlenwasserstoffe wie Benzol, Toluol, Xylol, Cyclohexanon, Isophoron, Dimethylsulfoxid, Dimethylformamid, weiterhin Mineralölfraktionen und Pflanzenöle.Suitable liquid carriers are, for example, aliphatic and aromatic Hydrocarbons such as benzene, toluene, xylene, cyclohexanone, isophorone, Dimethyl sulfoxide, dimethylformamide, mineral oil fractions and Vegetable oils.

Als feste Trägerstoffe eignen sich Mineralien, zum Beispiel Bentonit, Silicagel, Talkum, Kaolin, Attapulgit, Kalkstein, und pflanzliche Produkte, zum Beispiel Mehle.Minerals are suitable as solid carriers, for example bentonite, silica gel, Talc, kaolin, attapulgite, limestone, and herbal products, for Example flour.

An oberflächenaktiven Stoffen sind zu nennen zum Beispiel Calciumligninsulfonat, Polyethylenalkylphenylether, Naphthalinsulfonsäuren und deren Salze, Phenolsulfonsäuren und deren Salze, Formaldehydkondensate, Fettalkoholsulfate sowie substituierte Benzolsulfonsäuren und deren Salze.Examples of surface-active substances include calcium lignin sulfonate, Polyethylene alkylphenyl ether, naphthalenesulfonic acids and their salts, Phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates as well as substituted benzenesulfonic acids and their salts.

Der Anteil des beziehungsweise der Wirkstoffe(s) in den verschiedenen Zube­ reitungen kann in weiten Grenzen variieren. Beispielsweise enthalten die Mittel etwa 10 bis 90 Gewichtsprozent Wirkstoff, etwa 90 bis 10 Gewichts­ prozent flüssige oder feste Trägerstoffe sowie gegebenenfalls bis zu 20 Ge­ wichtsprozent oberflächenaktive Stoffe.The proportion of the active ingredient (s) in the various accessories Horse riding can vary widely. For example, the Average about 10 to 90 weight percent active ingredient, about 90 to 10 weight percent liquid or solid carriers and optionally up to 20 Ge percent by weight of surface-active substances.

Die Ausbringung der Mittel kann in üblicher Weise erfolgen, zum Beispiel mit Wasser als Träger in Spritzbrühmengen etwa 100 bis 1000 Liter/ha. Eine Anwendung der Mittel im sogenannten Low-Volume und Ultra-Low-Volume-Verfahren ist ebenso möglich wie ihre Applikation in Form von sogenannten Mikro­ granulaten. The funds can be applied in the customary manner, for example with water as a carrier in spray liquor quantities about 100 to 1000 liters / ha. A Use of the funds in the so-called low-volume and ultra-low-volume process is just as possible as their application in the form of so-called micro granules.  

Die Herstellung dieser Zubereitungen kann in an sich bekannter Art und Weise, zum Beispiel durch Mahl- oder Mischverfahren, durchgeführt werden. Ge­ wünschtenfalls können Zubereitungen der Einzelkomponenten auch erst kurz vor ihrer Verwendung gemischt werden, wie es zum Beispiel im sogenannten Tankmixverfahren in der Praxis durchgeführt wird. These preparations can be prepared in a manner known per se, for example by grinding or mixing processes. Ge if desired, preparations of the individual components can also be made only briefly be mixed before use, for example in the so-called Tank mix procedure is carried out in practice.  

Zur Herstellung der verschiedenen Zubereitungen werden zum Beispiel die folgenden Bestandteile eingesetzt:For the preparation of the various preparations, for example following components:

A) Spritzpulver
1.) 20 Gewichtsprozent Wirkstoff
68 Gewichtsprozent Kaolin
10 Gewichtsprozent Calciumsalz der Ligninsulfonsäure
 2 Gewichtsprozent DialkylnaphthalinsulfonatA) wettable powder
1.) 20 percent by weight of active ingredient
68 weight percent kaolin
10 weight percent calcium salt of lignin sulfonic acid
2 percent by weight dialkylnaphthalenesulfonate

2.) 40 Gewichtsprozent Wirkstoff
25 Gewichtsprozent Kaolin
25 Gewichtsprozent kolloidale Kieselsäure
 8 Gewichtsprozent Calciumsalz der Ligninsulfonsäure
 2 Gewichtsprozent Natriumsalz des N-Methyl-N-oleyl-taurins2.) 40 percent by weight of active ingredient
25% by weight kaolin
25 percent by weight colloidal silica
8 weight percent calcium salt of lignin sulfonic acid
2 percent by weight sodium salt of N-methyl-N-oleyl-taurine

B) Emulsionskonzentrat
20 Gewichtsprozent Wirkstoff
75 Gewichtsprozent Isophoron
 2 Gewichtsprozent ethoxyliertes Rizinusöl
 3 Gewichtsprozent Calciumsalz der DodecylphenylsulfonsäureB) emulsion concentrate
20 percent by weight of active ingredient
75 weight percent isophorone
2% by weight of ethoxylated castor oil
3 percent by weight calcium salt of dodecylphenylsulfonic acid

Die folgenden Beispiele erläutern die Herstellung der erfindungsgemäßen Verbindungen:The following examples illustrate the preparation of the invention Links:

Beispiel 1Example 1 8-Chlor-3-(2,4-dichlorphenyl)-1,2,4-triazolo[4,3-a]pyridin8-chloro-3- (2,4-dichlorophenyl) -1,2,4-triazolo [4,3-a] pyridine

5,0 g (15,8 mmol) 2′-(3-Chlor-2-pyridyl)-2,4-dichlorbenzoesäurehydrazid werden mit 7,4 ml (79 mmol) Phosphoroxychlorid 5 Stunden am Rückfluß er­ hitzt. Nach dem Erkalten der Reaktionsmischung wird mit gesättigter Natrium­ hydrogencarbonatlösung hydrolysiert und anschließend mit Essigester ex­ trahiert. Nach Trocknen (Magnesiumsulfat), Abziehen des Lösungsmittels im Vakuum und Umkristallisation des Rückstandes aus Diisopropylether erhält man die Titelverbindung.5.0 g (15.8 mmol) 2 '- (3-chloro-2-pyridyl) -2,4-dichlorobenzoic acid hydrazide are refluxed with 7.4 ml (79 mmol) of phosphorus oxychloride for 5 hours is heating. After the reaction mixture has cooled, it is saturated with sodium Hydrolysed hydrogen carbonate solution and then with ethyl acetate ex trahed. After drying (magnesium sulfate), stripping off the solvent in Vacuum and recrystallization of the residue from diisopropyl ether one the title link.

Ausbeute: 2,76 g=58% der Theorie; Fp.: 169°CYield: 2.76 g = 58% of theory; Mp: 169 ° C

Beispiel 2Example 2 8-Chlor-3-(phenylmethyl)-1,2,4-triazolo[4,3-a]pyridin8-chloro-3- (phenylmethyl) -1,2,4-triazolo [4,3-a] pyridine

Zu einer Lösung von 4,0 g (16,3 mmol) Phenylacetaldehyd-3-chlor-2-pyridyl­ hydrazon und 4,0 g (48,9 mmol) Natriumacetat in 160 ml Eisessig wird eine Lösung von 2,6 g (16,3 mmol) Brom in 32 ml Eisessig getropft. Das Gemisch wird für 30 Minuten bei Raumtemperatur nachgerührt und anschließend in 640 ml Eiswasser gegeben. Extraktion mit Dichlormethan liefert nach Trocknen (Magnesiumsulfat), Einrotieren und Umkristallisation die Titelverbindung.To a solution of 4.0 g (16.3 mmol) of phenylacetaldehyde-3-chloro-2-pyridyl hydrazone and 4.0 g (48.9 mmol) sodium acetate in 160 ml glacial acetic acid Solution of 2.6 g (16.3 mmol) of bromine in 32 ml of glacial acetic acid was added dropwise. The mixture is stirred for 30 minutes at room temperature and then in 640 ml Given ice water. Extraction with dichloromethane provides after drying (Magnesium sulfate), spinning in and recrystallization the title compound.

Ausbeute: 2,41 g=60,7% der Theorie; Fp.: 105-107°CYield: 2.41 g = 60.7% of theory; Mp .: 105-107 ° C

Analog zu den Beispielen wurden auch die folgenden erfindungsgemäßen Ver­ bindungen hergestellt:Analogously to the examples, the following ver bindings made:

Die folgenden Beispiele erläutern die Anwendungsmöglichkeiten der erfindungsgemäßen Verbindungen.The following examples explain the possible uses of the invention Links.

Beispiel AExample A

Im Gewächshaus wurden die aufgeführten Pflanzenspezies nach dem Auflaufen mit den aufgeführten Verbindungen in einer Aufwandmenge von 1,0 kg Wirk­ stoff/ha behandelt. Die Verbindungen wurden zu diesem Zweck als Emulsionen oder Suspensionen mit 500 Litern Wasser/ha gleichmäßig über die Pflanzen versprüht. Hier zeigte zwei Wochen nach der Behandlung die erfindungsgemäße Verbindung eine hohe Kulturpflanzenselektivität in Baumwolle und Mais bei ausgezeichneter Wirkung gegen das Unkraut. Das Vergleichsmittel zeigte nicht die gleichhohe Selektivität.The plant species listed were in the greenhouse after emergence with the listed compounds in an application rate of 1.0 kg of active ingredient fabric / ha treated. The compounds were used as emulsions for this purpose or suspensions with 500 liters of water / ha evenly over the plants sprayed. Here showed the invention according to the invention two weeks after the treatment Compound a high crop selectivity in cotton and corn excellent action against weeds. The comparative showed not the same selectivity.

In der folgenden Tabelle bedeuten:In the following table mean:

0 = keine Schädigung
1 = 1-24% Schädigung
2 = 25-74% Schädigung
3 = 75-89% Schädigung
4 = 90-100% Schädigung0 = no damage
1 = 1-24% damage
2 = 25-74% damage
3 = 75-89% damage
4 = 90-100% damage

GOSHI = Gossypium hirsutum
TRZAX = Triticum aestivum
ZEAMX = Zea mays
ABUTH = Abutilon theophrasti
IPOSS = Ipomoea purpurea
MATCH = Matricaria chamomilla
SEBEX = Sesbania exaltata
SOLSS = Solanum sp. GOSHI = Gossypium hirsutum
TRZAX = Triticum aestivum
ZEAMX = Zea mays
ABUTH = Abutilon theophrasti
IPOSS = Ipomoea purpurea
MATCH = Matricaria chamomilla
SEBEX = Sesbania exaltata
SOLSS = Solanum sp.

Beispiel BExample B

Im Gewächshaus wurden die aufgeführten Pflanzenspezies vor dem Auflaufen mit den aufgeführten Verbindungen in einer Aufwandmenge von 0,3 kg Wirk­ stoff/ha behandelt. Die Verbindungen wurden zu diesem Zweck als Emulsionen oder Suspensionen mit 500 Litern Wasser/ha gleichmäßig über den Boden ver­ sprüht. Hier zeigte drei Wochen nach der Behandlung die erfindungsgemäße Verbindung eine hohe Kulturpflanzenselektivität in Baumwolle und Mais bei ausgezeichneter Wirkung gegen das Unkraut. Das Vergleichsmittel zeigte nicht die gleichhohe Wirksamkeit.The plant species listed were in the greenhouse before emergence with the listed compounds in an application rate of 0.3 kg of active ingredient fabric / ha treated. The compounds were used as emulsions for this purpose or suspensions with 500 liters of water / ha evenly over the soil sprays. Here three weeks after the treatment showed the invention Compound a high crop selectivity in cotton and corn excellent action against weeds. The comparative showed not the same effectiveness.

In der folgenden Tabelle bedeuten:In the following table mean:

0 = keine Schädigung
1 = 1-24% Schädigung
2 = 25-74% Schädigung
3 = 75-89% Schädigung
4 = 90-100% Schädigung0 = no damage
1 = 1-24% damage
2 = 25-74% damage
3 = 75-89% damage
4 = 90-100% damage

GOSHI = Gossypium hirsutum
ZEAMX = Zea mays
GALAP = Galium aparine
VERPE = Veronica persicaGOSHI = Gossypium hirsutum
ZEAMX = Zea mays
GALAP = Galium aparine
VERPE = Veronica persica

Claims (5)

1. Mittel mit herbizider Wirkung, gekennzeichnet durch einen Gehalt an mindestens einem substituierten 1,2,4-Triazolo[4,3-a]pyridin der allgemeinen Formel I in der
R¹ einen Phenylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₃-C₆-Cycloal­ kyl, Halogen-C₃-C₆-cycloalkyl, Phenyl-C₁-C₆-alkyl, C₂-C₆-Alkenyl, Halo­ gen-C₂-C₆-alkenyl, Phenyl-C₂-C₆-alkenyl, C₂-C₆-Alkinyl, Halogen-C₂-C₆- alkinyl, Phenyl-C₂-C₆-alkinyl, C₁-C₆-Alkoxy, Halogen-C₁-C₆-alkoxy, C₁- C₄-Alkoxy-C₁-C₆-alkoxy, C₁-C₄-Alkylamino-C₁-C₆-alkoxy, Di-C₁-C₄-alkyl­ amino-C₁-C₆-alkoxy, C₂-C₆-Alkenyloxy, Mercapto, C₁-C₆-Alkylthio, Halo­ gen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkyl­ carbonyl, Halogen-C₁-C₆-alkylcarbonyl, C₁-C₆-Alkoxycarbonyl, Phenyl, Halogenphenyl, C₁-C₆-Alkylphenyl, Phenoxy, Halogenphenoxy, C₁-C₆-Alkyl­ phenoxy, Nitrophenoxy, Amino, C₁-C₄-Alkylamino, Di-.C₁-C₄-alkylamino, Phenylamino, Halogenphenylamino, C₁-C₆-Alkylphenylamino, Cyano, Nitro, Methylendioxy, Ethylidendioxy oder Isopropylidendioxy substituierten Phenylrest, einen Naphthylrest oder einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Hydroxy, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, Ami­ no, C₁-C₄-Alkylamino, Di-C₁-C₄-alkylamino, Cyano oder Nitro substituierten Naphthylrest,
R² Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆-Alkoxy, Halo­ gen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkyl­ sulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl-C₁-C₆-alkoxy­ carbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁-C₄-alkylamino, Cyano oder Nitro,
R³ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁- C₄-alkylamino, Cyano oder Nitro,
R⁴ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁- C₄-alkylamino, Cyano oder Nitro,
R⁵ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁- C₄-alkylamino, Cyano oder Nitro und
n 0 oder 1
bedeuten.1. Agents with herbicidal activity, characterized by a content of at least one substituted 1,2,4-triazolo [4,3-a] pyridine of the general formula I. in the
R¹ is a phenyl radical, one or more, the same or different, by halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₃-C₆-cycloalyl, halogen-C₃-C₆-cycloalkyl, phenyl-C₁ -C₆-alkyl, C₂-C₆-alkenyl, halo gene-C₂-C₆-alkenyl, phenyl-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halogen-C₂-C₆-alkynyl, phenyl-C₂-C₆-alkynyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₆-alkoxy, C₁-C₄-alkylamino-C₁-C₆-alkoxy, di-C₁-C₄-alkyl amino-C₁-C₆ -alkoxy, C₂-C₆-alkenyloxy, mercapto, C₁-C₆-alkylthio, halo gene-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkyl carbonyl, halogen-C₁-C₆ -alkylcarbonyl, C₁-C₆-alkoxycarbonyl, phenyl, halophenyl, C₁-C₆-alkylphenyl, phenoxy, halophenoxy, C₁-C₆-alkyl phenoxy, nitrophenoxy, amino, C₁-C₄-alkylamino, di-.C₁-C₄-alkylamino, phenylamino , Halogenphenylamino, C₁-C₆-alkylphenylamino, cyano, nitro, methylenedioxy, ethyl lidendioxy or isopropylidenedioxy substituted phenyl, a naphthyl or one or more, the same or different, by halogen, hydroxy, C₁-C₄-alkyl, C₁-C₄-alkoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄- alkylamino, cyano or nitro substituted naphthyl,
R² halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁- C₆-alkyl sulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl-C₁-C₆-alkoxy carbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano or nitro,
R³ is hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl- C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁- C₄-alkylamino, cyano or nitro,
R⁴ hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl- C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁- C₄-alkylamino, cyano or nitro,
R⁵ hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl-C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano or nitro and
n 0 or 1
mean. 2. Verwendung von Mitteln gemäß Anspruch 1 zur Bekämpfung monokotyler und dikotyler Unkrautarten in landwirtschaftlichen Hauptkulturen.2. Use of agents according to claim 1 for combating monocotyledons and dicotyledonous weed species in main agricultural crops. 3. Verfahren zur Herstellung von Mitteln mit herbizider Wirkung, dadurch gekennzeichnet, daß man substituierte 1,2,4-Triazolo[4,3-a]pyridine der allgemeinen Formel I gemäß Anspruch 1 mit Träger- und/oder Hilfsstoffen vermischt.3. Process for the preparation of compositions with herbicidal activity, thereby characterized in that substituted 1,2,4-triazolo [4,3-a] pyridines of general formula I according to claim 1 with carriers and / or auxiliaries mixed. 4. Substituierte 1,2,4-Triazolo[4,3-a]pyridine der allgemeinen Formel Ia R¹* einen Phenylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl, Phenyl-C₁-C₆-alkyl, C₂-C₆-Alkenyl, Halogen- C₂-C₆-alkenyl, Phenyl-C₂-C₆-alkenyl, C₂-C₆-Alkinyl, Halogen-C₂-C₆- alkinyl, Phenyl-C₂-C₆-alkinyl, C₁-C₆-Alkoxy, Halogen-C₁-C₆-alkoxy, C₁- C₄-Alkoxy-C₁-C₆-alkoxy, C₁-C₄-Alkylamino-C₁-C₆-alkoxy, Di-C₁-C₄-alkyl­ amino-C₁-C₆-alkoxy, C₂-C₆-Alkenyloxy, Mercapto, C₁-C₆-Alkylthio, Halogen- C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Al­ kylcarbonyl, Halogen-C₁-C₆-alkylcarbonyl, C₁-C₆-Alkoxycarbonyl, Phenyl, Halogenphenyl, C₁-C₆-Alkylphenyl, Phenoxy, Halogenphenoxy, C₁-C₆-Alkyl­ phenoxy, Nitrophenoxy, Amino, C₁-C₄-Alkylamino. Di-C₁-C₄-alkylamino, Phenylamino, Halogenphenylamino, C₁-C₆-Alkylphenylamino, Cyano, Nitro, Methylendioxy, Ethylidendioxy oder Isopropylidendioxy substituierten Phenylrest, einen Naphthylrest oder einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Hydroxy, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, Amino, C₁-C₄-Alkylamino, Di-C₁-C₄-alkylamino, Cyano oder Nitro substituierten Naphthylrest,
R²* Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆-Alkoxy, Halo­ gen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkyl­ sulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl-C₁-C₆-alkoxy­ carbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁-C₄-alkylamino, Cyano oder Nitro, mit der Einschränkung, daß R²* nicht Brom oder Methyl ist, wenn R¹* Phenyl und n* 0 ist, und R²* nicht Nitro ist, wenn R¹* 4-Methoxyphenyl und n* 0 ist.
R³ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁- C₄-alkylamino, Cyano oder Nitro,
R⁴ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Ci-C₁- C₄-alkylamino, Cyano oder Nitro,
R⁵ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Alkoxy, Halogen-C₁-C₆-alkoxy, C₁-C₆-Alkylthio, Halogen-C₁-C₆-alkylthio, C₁-C₆-Alkylsulfinyl, C₁-C₆-Alkylsulfonyl, C₁-C₆-Alkoxycarbonyl, Phenyl- C₁-C₆-alkoxycarbonyl, Phenyl, Phenoxy, Amino, C₁-C₄-Alkylamino, Di-C₁-C₄- alkylamino, Cyano oder Nitro und
n* 0 oder 1
bedeuten.4. Substituted 1,2,4-triazolo [4,3-a] pyridines of the general formula Ia R¹ * is a phenyl radical, one or more, the same or different, by halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, phenyl-C₁ -C₆-alkyl, C₂-C₆-alkenyl, halogen- C₂-C₆-alkenyl, phenyl-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halogen-C₂-C₆-alkynyl, phenyl-C₂-C₆-alkynyl, C₁ -C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁- C₄-alkoxy-C₁-C₆-alkoxy, C₁-C₄-alkylamino-C₁-C₆-alkoxy, di-C₁-C₄-alkyl amino-C₁-C₆- alkoxy, C₂-C₆-alkenyloxy, mercapto, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylcarbonyl, halogen-C₁-C₆-alkylcarbonyl , C₁-C₆-alkoxycarbonyl, phenyl, halophenyl, C₁-C₆-alkylphenyl, phenoxy, halophenoxy, C₁-C₆-alkyl phenoxy, nitrophenoxy, amino, C₁-C₄-alkylamino. Di-C₁-C₄-alkylamino, phenylamino, halophenylamino, C₁-C₆-alkylphenylamino, cyano, nitro, methylenedioxy, ethylidendioxy or isopropylidendioxy substituted phenyl radical, a naphthyl radical or a one or more, identical or different, halogen or hydroxy, C₁-C₄ -Alkyl, C₁-C₄-alkoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano or nitro substituted naphthyl,
R² * halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkyl sulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl-C₁-C₆-alkoxy carbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano or nitro , with the restriction that R² * is not bromine or methyl when R¹ * is phenyl and n * 0, and R² * is not nitro when R¹ * is 4-methoxyphenyl and n * 0.
R³ is hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl- C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁- C₄-alkylamino, cyano or nitro,
R⁴ hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl- C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, Ci-C₁- C₄-alkylamino, cyano or nitro,
R⁵ hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-alkoxy, halogen-C₁-C₆-alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆-alkylthio, C₁ -C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl-C₁-C₆-alkoxycarbonyl, phenyl, phenoxy, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano or nitro and
n * 0 or 1
mean. 5. Verfahren zur Herstellung von Verbindungen der allgemeinen Formel Ia gemäß Anspruch 4, dadurch gekennzeichnet, daß man in an sich bekannter Weise
  • A) eine Verbindung der allgemeinen Formel II in der R¹*, R²*, R³, R⁴, R⁵ und n* die unter der allgemeinen Formel Ia angegebenen Bedeutungen haben, mit einem Halogenierungsmittel umsetzt oder
  • B) eine Verbindung der allgemeinen Formel III in der R¹*, R²*, R³*, R⁴, und R⁵ und n* die unter der allgemeinen Formel Ia angegebenen Bedeutungen haben, mit einem Oxydationsmittel zur Reaktion bringt.
5. A process for the preparation of compounds of general formula Ia according to claim 4, characterized in that in a manner known per se
  • A) a compound of general formula II in which R¹ *, R² *, R³, R⁴, R⁵ and n * have the meanings given under the general formula Ia, reacted with a halogenating agent or
  • B) a compound of the general formula III in which R¹ *, R² *, R³ *, R⁴, and R⁵ and n * have the meanings given under the general formula Ia, reacting with an oxidizing agent.
DE19893939892 1989-11-30 1989-11-30 New triazolo-(4,3-a)pyridine(s) and N'-(2-pyridyl)-hydrazone(s) Withdrawn DE3939892A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DE19893939892 DE3939892A1 (en) 1989-11-30 1989-11-30 New triazolo-(4,3-a)pyridine(s) and N'-(2-pyridyl)-hydrazone(s)
IL96432A IL96432A0 (en) 1989-11-30 1990-11-21 Pesticidal compositions containing pyridine derivatives and novel pyridine derivatives
JP2323362A JPH03181463A (en) 1989-11-30 1990-11-28 Herbicidal agent, substituted 1, 2, 4- triazol-(4, 3-a) pyridine and method of destroying weed
PT96034A PT96034A (en) 1989-11-30 1990-11-29 PROCESS FOR THE PREPARATION OF SUBSTITUTED N '- (2-PYRIDYL) ALDEED 1,2,4-TRIAZOLE (4,3-A) PYRIDINES AND SUBSTITUTED N' - (2-PYRIDYL) HYDRAXES
BR909006067A BR9006067A (en) 1989-11-30 1990-11-29 HERBICIDE COMPOSITION, PROCESS FOR COMBATING WEEDS, PROCESSES FOR PREPARING A REPLACED 1,2,4-TRIAZOLE- (4,3-A) PYRIDINE AND A N '- (2-PYRIDIL) REPLACED HYDRAZONE, AS WELL AS 1, 2,4-TRIAZOLO- (4,3-A) REPLACED PYRIDINES AND N '- (2-PYRIDYL) REPLACED HYDRAZONS
KR1019900019667A KR910009155A (en) 1989-11-30 1990-11-29 Substituted 1,2,4-triazolo [4,3-a] pyridine and substituted N '-(2-pyridyl) aldehyde hydrazones and their use as herbicides
EP19900250296 EP0430385A3 (en) 1989-11-30 1990-11-29 Substituted 1,2,4-triazolo-(4,3-a)pyridines, and substituted n'-(2-pyridyl)-hydrazones, and their use as herbicides
CN90109686A CN1052238A (en) 1989-11-30 1990-11-30 Replace 1,2, N '-(2-pyridine radicals) the aldehyde hydrazone of 4-triazol [4,3-α] pyridine and replacement and as herbicide applications

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