DE4012040A1 - 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)Info
- Publication number
- DE4012040A1 DE4012040A1 DE19904012040 DE4012040A DE4012040A1 DE 4012040 A1 DE4012040 A1 DE 4012040A1 DE 19904012040 DE19904012040 DE 19904012040 DE 4012040 A DE4012040 A DE 4012040A DE 4012040 A1 DE4012040 A1 DE 4012040A1
- Authority
- DE
- Germany
- Prior art keywords
- halogen
- alkyl
- cyano
- cycloalkyl
- cycloalkenyl
- 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- Withdrawn
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Classifications
-
- 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
Description
Die Erfindung betrifft die Verwendung von teilweise bekannten substituierten N′-(2-Pyridyl)-aldehydhydrazonen als Mittel mit herbizider Wirkung.The invention relates to the use of partially known substituted N '- (2-pyridyl) -aldehyde hydrazone as a herbicidal agent.
Es ist bekannt, daß bestimmte N′-(2-Pyridyl)-benzaldehydhydrazone pharmakologische Eigenschaften besitzen (US-PS 41 21 036). Über eine herbizide Wirkung dieser Verbindungsklasse ist bisher nichts bekannt.It is known that certain N '- (2-pyridyl) benzaldehyde hydrazones are pharmacological Have properties (US-PS 41 21 036). About a herbicidal effect nothing is known about this class of compound.
Es wurde nun gefunden, daß Mittel enthaltend teilweise bekannte substituierte N′-(2-Pyridyl)-aldehydhydrazone der allgemeinen Formel IIt has now been found that compositions containing partially known Substituted N '- (2-pyridyl) aldehyde hydrazones of the general formula I
in der
R¹ einen C₁-C₁₀-Alkylrest, einen ein- oder mehrfach, gleich oder verschieden
durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl,
Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄-alkyl-
C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl,
Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄-Alkyl-
C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl oder
Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₁-C₁₀-Alkylrest, einen
C₂-C₁₀-Alkenylrest, einen ein- oder mehrfach, gleich oder verschieden
durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl,
Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄-alkyl-
C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl,
Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄-Alkyl-
C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl oder Cyano-
C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₂-C₁₀-Alkenylrest;
einen C₂-C₁₀-Alkinylrest, einen ein- oder mehrfach, gleich oder verschieden
durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl,
Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄-
alkyl-C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl,
Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄-
Alkyl-C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl oder
Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₂-C₁₀-Alkinylrest,
einen C₃-C₈-Cycloalkylrest, einen ein- oder mehrfach, gleich oder verschieden
durch Halogen, Cyano, C₁-C₄-Alkyl, Halogen-C₁-C₄-alkyl, Cyano-
C₁-C₄-alkyl, C₂-C₄-Alkenyl, Halogen-C₂-C4-alkenyl, Cyano-C₂-C₄-alkenyl,
C₂-C₄-Alkinyl, Halogen-C₂-C₄-alkinyl oder Cyano-C₂-C₄-alkinyl substituierten
C₃-C₈-Cycloalkylrest, einen C₃-C₈-Cycloalkenylrest, einen ein-
oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₁-C₄-Alkyl,
Halogen-C₁-C₄-alkyl, Cyano-C₁-C₄-alkyl, C₂-C₄-Alkenyl, Halogen-C₂-C₄-
alkenyl, Cyano-C₂-C₄-alkenyl, C₂-C₄-Alkinyl, Halogen-C₂-C₄-alkinyl
oder Cyano-C₂-C₄-alkinyl substituierten C₃-C₈-Cycloalkenylrest, einen
Phenylrest oder einen ein- oder mehrfach, gleich oder verschieden durch
Halogen, Hydroxy, C₁-C₄-Alkyl, Halogen-C₁-C₄-alkyl, C₁-C₄-Alkoxy, Halogen-
C₁-C₄-alkoxy, Mercapto, C₁-C₄-Alkylthio, Halogen-C₁-C₄-alkylthio,
C₁-C₄-Alkylsulfinyl, C₁-C₄-Alkylsulfonyl, C₁-C₄-Alkoxycarbonyl, Phenyl,
Amino, C₁-C₄-Alkylamino, Di-C₁-C₄-Alkylamino, Cyano, Nitro, Methylendioxy,
Ethylendioxy oder Isopropylidendioxy substituierten Phenylrest,
R² 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,
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 und
R⁵ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆-
Akoxy, 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
bedeuten, überraschenderweise eine ausgeprägte herbizide Wirkung besitzen.in the
R¹ is a C₁-C₁₀ alkyl radical, one or more, the same or different, by halogen, cyano, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₄-alkyl- C₃-C₆-cycloalkyl, halogen-C₁-C₄-alkyl- C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, cyano- C₃-C₆-cycloalkenyl, C₁-C₄-alkyl-C₃-C₆-cycloalkenyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl-substituted C₁-C₁₀- Alkyl radical, a C₂-C₁₀ alkenyl radical, one or more, the same or different by halogen, cyano, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₄-alkyl -C₃-C₆-cycloalkyl, halogen-C₁-C₄-alkyl- C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, cyano -C₃-C₆-cycloalkenyl, C₁-C₄-alkyl- C₃-C ₆-cycloalkenyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituted C₂-C₁₀ alkenyl; a C₂-C₁₀ alkynyl radical, one or more, identical or different by halogen, cyano, C₃-C--cycloalkyl, halogen-C₃-C--cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃ -C₆-cycloalkyl, halogen-C₁-C₄- alkyl-C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, cyano-C₃ -C₆-cycloalkenyl, C₁-C₄- alkyl-C₃-C₆-cycloalkenyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituted C₂-C₁₀ alkynyl , a C₃-C₈-cycloalkyl radical, one or more, identical or different by halogen, cyano, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkenyl, Halogen-C₂-C4-alkenyl, cyano-C₂-C₄-alkenyl, C₂-C₄-alkynyl, halogen-C₂-C₄-alkynyl or cyano-C₂-C₄-alkynyl substituted C₃-C₈-cycloalkyl radical, a C₃-C₈-cycloalkenyl radical , one or more, the same o the different by halogen, cyano, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkenyl, halogen-C₂-C₄-alkenyl, cyano-C₂-C₄-alkenyl , C₂-C₄-alkynyl, halogen-C₂-C₄-alkynyl or cyano-C₂-C₄-alkynyl substituted C₃-C₈-cycloalkenyl radical, a phenyl radical or one or more, the same or different, by halogen, hydroxy, C₁-C₄- Alkyl, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, mercapto, C₁-C₄-alkylthio, halogen-C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄- Alkylsulfonyl, C₁-C₄-alkoxycarbonyl, phenyl, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano, nitro, methylenedioxy, ethylenedioxy or isopropylidenedioxy substituted phenyl radical,
R² 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-C₁-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl-C₁-C₆-alkoxycarbonyl, 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 and
R⁵ hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-acoxy, 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
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", "Halogenalkenyl", "Halogenalkinyl", "Halogencycloalkyl", "Halogencycloalkenyl", "Halogenalkylcycloalkyl" oder "Halogenalkylcycloalkenyl" bedeutet, daß ein oder mehrere Wasserstoffatome durch Fluor, Chlor, Brom oder Jod ersetzt sind."Haloalkyl", "haloalkenyl", "haloalkynyl", "halocycloalkyl", "Halocycloalkenyl", "haloalkylcycloalkyl" or "haloalkylcycloalkenyl" means that one or more hydrogen atoms by fluorine, chlorine, Bromine or iodine are replaced.
"Cyanoalkyl", "Cyanoalkenyl", "Cyanoalkinyl", "Cyanocycloalkyl", "Cyanocycloalkenyl", "Cyanoalkylcycloalkyl" oder "Cyanoalkylcycloalkenyl" bedeutet, daß ein- oder mehrere Wasserstoffatome durch Cyano ersetzt sind."Cyanoalkyl", "cyanoalkenyl", "cyanoalkinyl", "cyanocycloalkyl", "cyanocycloalkenyl", Means "cyanoalkylcycloalkyl" or "cyanoalkylcycloalkenyl", that one or more hydrogen atoms are replaced by cyano.
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 N′-(2-Pyridyl)-aldehydhydrazone der allgemeinen Formel I sind teilweise bekannt (Khim. Geterotsikl. Soedin, 6 (1974) 792, Ukr. Khim. Zh. 35 (1969) 524, Rocz. Chem. 41 (1967) 483).The substituted N '- (2-pyridyl) aldehyde hydrazones which can be used according to the invention general formula I are known in part (Khim. Geterotsikl. Soedin, 6 (1974) 792, Ukr. Khim. Zh. 35 (1969) 524, Rocz. Chem. 41 (1967) 483).
Noch nicht bekannt sind jedoch die substituierten N′-(2-Pyridyl)-aldehydhydrazone der allgemeinen Formel IaHowever, the substituted N ′ - (2-pyridyl) aldehyde hydrazones are not yet known of the general formula Ia
in der
R¹* einen C₁-C₁₀-Alkylrest, einen ein- oder mehrfach, gleich oder verschieden
durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl,
Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄-
alkyl-C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl,
Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄-
Alkyl-C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl oder
Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₁-C₁₀-Alkylrest,
einen C₂-C₁₀-Alkenylrest, einen ein- oder mehrfach, gleich oder verschieden
durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl,
Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄-
alkyl-C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl,
Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄-
Alkyl-C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl oder
Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₂-C₁₀-Alkenylrest,
einen C₂-C₁₀-Alkinylrest, einen ein- oder mehrfach, gleich oder verschieden
durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl,
Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄-
alkyl-C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl,
Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄-
Alkyl-C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl oder
Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₂-C₁₀-Alkinylrest,
einen C₃-C₈-Cycloalkylrest, einen ein- oder mehrfach, gleich oder verschieden
durch Halogen, Cyano, C₁-C₄-Alkyl, Halogen-C₁-C₄-alkyl, Cyano-
C₁-C₄-alkyl, C₂-C₄-Alkenyl, Halogen-C₂-C4-alkenyl, Cyano-C₂-C₄-alkenyl,
C₂-C₄-Alkinyl, Halogen-C₂-C₄-alkinyl oder Cyano-C₂-C₄-alkinyl substituierten
C₃-C₈-Cycloalkylrest, einen C₃-C₈-Cycloalkenylrest, einen ein-
oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₁-C₄-Alkyl,
Halogen-C₁-C₄-alkyl, Cyano-C₁-C₄-alkyl, C₂-C₄-Alkenyl, Halogen-C₂-C₄-
alkenyl, Cyano-C₂-C₄-alkenyl, C₂-C₄-Alkinyl, Halogen-C₂-C₄-alkinyl
oder Cyano-C₂-C₄-alkinyl substituierten C₃-C₈-Cycloalkenylrest, einen
Phenylrest oder einen ein- oder mehrfach, gleich oder verschieden durch
Halogen, Hydroxy, C₁-C₄-Alkyl, Halogen-C₁-C₄-alkyl, C₁-C₄-Alkoxy, Halogen-
C₁-C₄-alkoxy, Mercapto, C₁-C₄-Alkylthio, Halogen-C₁-C₄-alkylthio,
C₁-C₄-Alkylsulfinyl, C₁-C₄-Alkylsulfonyl, C₁-C₄-Alkoxycarbonyl, Phenyl,
Amino, C₁-C₄-Alkylamino, Di-C₁-C₄-Alkylamino, Cyano, Nitro, Methylendioxy,
Ethylendioxy oder Isopropylidendioxy substituierten Phenylrest,
R²* 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, C₁-C₄-Alkylamino, Di-C₁-C₄-alkylamino, oder
Cyano, mit der Einschränkung, daß R²* nicht Brom ist, wenn R¹* Phenyl
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, Di-C₁-C₄-
alkylamino, Cyano oder Nitro, mit der Einschränkung, daß R⁴* nicht
Nitro ist, wenn R¹* Phenyl und R²* Methyl sind, und
R⁵* Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆-
Akoxy, 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, mit der Einschränkung, daß R⁵* nicht
Methyl ist, wenn R¹* Phenyl und R²* und R⁴* Chlor sind,
bedeuten.in the
R¹ * is a C₁-C₁₀ alkyl radical, one or more, identical or different by halogen, cyano, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₁-alkyl -C₃-C₆-cycloalkyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, cyano -C₃-C₆-cycloalkenyl, C₁-C₄- alkyl-C₃-C₆-cycloalkenyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituted C₁-C₁₀ -Alkyl radical, a C₂-C₁₀ alkenyl radical, one or more, the same or different, by halogen, cyano, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₄- Alkyl-C₃-C₆-cycloalkyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄- alkyl-C₃- C₆-Cycloalkenyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituted C₂-C₁₀-alkenyl radical, a C₂-C₁₀-alkynyl radical, one or more times , identical or different by halogen, cyano, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkyl, halogen-C₁-C₄- alkyl -C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, cyano-C₃-C₆-cycloalkenyl, C₁-C₄- alkyl-C₃ -C₆-cycloalkenyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituted C₂-C₁₀-alkynyl radical, a C₃-C₈-cycloalkyl radical, a one or multiple, identical or different by halogen, cyano, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, cyano- C₁-C₄-alkyl, C₂-C₄-alkenyl, halogen-C₂-C4-alkenyl, cyano-C₂- C₄-alkenyl, C₂-C₄-alkynyl, halogen -C₂-C₄-alkynyl or cyano-C₂-C₄-alkynyl substituted C₃-C₈-cycloalkyl radical, a C₃-C₈-cycloalkenyl radical, one or more, the same or different, by halogen, cyano, C₁-C₄-alkyl, halogen- C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkenyl, halogen-C₂-C₄-alkenyl, cyano-C₂-C₄-alkenyl, C₂-C₄-alkynyl, halogen-C₂-C₄-alkynyl or Cyano-C₂-C₄-alkynyl substituted C₃-C₈-cycloalkenyl radical, a phenyl radical or one or more, the same or different, by halogen, hydroxy, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy , Halogen C₁-C Halogen-alkoxy, mercapto, C₁-C₄-alkylthio, halogen-C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkoxycarbonyl, phenyl, amino, C₁-C₄ Alkylamino, di-C₁-C₄-alkylamino, cyano, nitro, methylenedioxy, ethylenedioxy or isopropylidenedioxy substituted phenyl radical,
R² * 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, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, or cyano, with the restriction that R² * is not bromine when R¹ * is phenyl,
R³ * 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, with the restriction that R⁴ * is not nitro when R¹ * is phenyl and R² * is methyl, and
R⁵ * hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-acoxy, 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, with the restriction that R⁵ * is not methyl when R¹ * is phenyl and R² * and R⁴ * are chlorine,
mean.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel I und Ia können auch als Tautomere mit den allgemeinen Formeln I′ und I′aThe compounds of general formula I and Ia according to the invention can also as tautomers with the general formulas I 'and I'a
oder als Isomere mit den allgemeinen Formeln I′′ und I′′aor as isomers with the general formulas I '' and I''a
vorliegen, in denen R¹, R², R³, R⁴ und R⁵ die unter der allgemeinen Formel I und R¹*, R²*, R³*, R⁴* und R⁵* die unter der allgemeinen Formel Ia angegebene Bedeutungen haben. Diese Strukturen werden ebenfalls durch die vorliegende Erfindung erfaßt, aus Gründen der Einfachheit werden aber jeweils nur die Strukturen der allgemeinen Formeln I und Ia angegeben.are present in which R¹, R², R³, R⁴ and R⁵ those under the general formula I. and R¹ *, R² *, R³ *, R⁴ * and R⁵ * those given under the general formula Ia Have meanings. These structures are also covered by the present Invention is recorded, but for reasons of simplicity only the structures of general formulas I and Ia are given.
Die Herstellung der noch nicht bekannten substituierten N′-(2-Pyridyl)- aldehydhydrazone läßt sich in Anlehnung an bekannte Methoden durchführen (zum Beispiel J. Chem. Soc. 1915, 688, Acta Chim. Scan. B 37 (1983), 527), indem man eine Verbindung der allgemeinen Formell IIThe preparation of the not yet known substituted N ′ - (2-pyridyl) - aldehyde hydrazones can be carried out based on known methods (for Example J. Chem. Soc. 1915, 688, Acta Chim. Scan. B 37 (1983), 527) by a compound of the general formula II
in der R²*, R³*, R⁴* und R⁵* die unter der allgemeinen Formel Ia angegebene Bedeutungen haben, mit einem Aldehyd der allgemeinen Formel III in the R² *, R³ *, R⁴ * and R⁵ * the given under the general formula Ia Have meanings with an aldehyde of the general formula III
in der R¹* die unter der allgemeinen Formel Ia angegebene Bedeutung hat, in Anwesenheit eines geeigneten Lösungsmittels zur Reaktion bringt.in which R¹ * has the meaning given under the general formula Ia, in the presence of a suitable solvent.
Die Herstellung kann mit oder ohne Lösungsmittel durchgeführt werden, wobei im Bedarfsfall solche Lösungs- beziehungsweise Verdünnungsmittel zum Einsatz kommen, die gegenüber den jeweiligen Reaktanden inert sind. Beispiele für solche Lösungsmittel beziehungsweise Verdünnungsmittel sind aliphatische, alicyclische und aromatische Kohlenwasserstoffe, die jeweils gegebenenfalls chloriert sein können, wie zum Beispiel Hexan, Cyclohexan, Petrolether, Ligroin, Benzol, Toluol, Xylol, Methylenchlorid, Chloroform, Kohlenstofftetrachlorid, Ethylenchlorid, Trichlorethylen und Chlorbenzol, Ether, wie zum Beispiel Diethylether, Methylethylether, Methyl-t-butylether, Diisopropylether, Dibutylether, Dioxan und Tetrahydrofuran, Ketone, wie zum Beispiel Aceton, Methylenethylketon, Methylisopropylketon und Methylisobutylketon, Nitrile, wie zum Beispiel Acetonitril und Propionitril, Alkohole, wie zum Beispiel Methanol, Ethanol, Isopropanol, 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 preparation can be carried out with or without a solvent, where If necessary, such solvents or diluents can be used come that are inert to the respective reactants. Examples such solvents or diluents are aliphatic, alicyclic and aromatic hydrocarbons, each optionally can be chlorinated, such as hexane, cyclohexane, petroleum ether, Ligroin, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, Ethylene chloride, trichlorethylene and chlorobenzene, ether, such as diethyl ether, methyl ethyl ether, methyl t-butyl ether, Diisopropyl ether, dibutyl ether, dioxane and tetrahydrofuran, ketones, such as Example acetone, methylene ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, Nitriles, such as, for example, acetonitrile and propionitrile, alcohols, such as methanol, ethanol, isopropanol, butanol, tert-butanol, tert-amyl alcohol and ethylene glycol, esters, such as ethyl acetate and amyl acetate, acid amides such as dimethylformamide and dimethylacetamide, Sulfoxides such as dimethyl sulfoxide and sulfones such as for example sulfolane, and bases such as pyridine and Triethylamine.
Alle Reaktionen werden vorzugsweise unter dem Druck der Umgebung durchgeführt, 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, although they are 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 dem oben genannten Verfahren hergestellten erfindungsgemäßen Verbindungen 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 compounds of the invention prepared by the above process 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 geruchlose 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 colorless and odorless 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 beschriebenen Herstellungsverfahren benötigten Hydrazine der allgemeinen Formel II sowie die Aldehyde der allgemeinen Formel III sind entweder literaturbekannt oder können in Anlehnung an literaturbekannte Methoden hergestellt werden. Einschlägige Techniken sind beispielsweise in J. Org. Chem. 27 (1962) 3965 für Hydrazine oder Synthesis 1988, 394 für Aldehyde beschrieben.The hydrazines required in the production process described general formula II and the aldehydes of general formula III either known from the literature or can be based on methods known from the literature getting produced. Relevant techniques are, for example, in J. Org. Chem. 27 (1962) 3965 for hydrazines or Synthesis 1988, 394 for aldehydes described.
Die erfindungsgemäßen Verbindungen zeigen eine gute herbizide Wirkung bei breitblättrigen Unkräutern und Gräsern. Ein selektiver Einsatz der erfindungsgemäßen Wirkstoffe ist in verschiedenen Kulturen möglich, zum Beispiel in Raps, Rüben, Sojabohnen, Baumwolle, Reis, Gerste, Weizen und anderen Getreidearten. 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 Unkrautbekämpfung 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 invention Active ingredients are possible in different cultures, for example in rapeseed, beets, soybeans, cotton, rice, barley, wheat and others 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 Weed 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, Matricaria, Anthemis, Galinsoga, Chenopodium, Brassica, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Lamium, Veronica, Abutilon, Datura, Viola, Galeopsis, Papaver, Centaurea und Chrysanthemum.Dicot weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Brassica, Urtica, Senecio, Amaranthus, 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, Echinoloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron, Sagittaria, Monochoria, Fimbristylis, Elocharis, Ischaemum und Apera.Monocot weeds of the genera Avena, Alopecurus, Echinoloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron, Sagittaria, Monochoria, Fimbristylis, Elocharis, 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 miteinander oder mit anderen Wirkstoffen angewendet werden. Gegebenenfalls können andere Pflanzenschutz- oder Schädlingsbekämpfungsmittel je nach dem gewünschten Zweck zugesetzt werden. Sofern eine Verbreiterung des Wirkungsspektrums beabsichtigt ist, können auch andere Herbizide zugesetzt werden.The compounds according to the invention can either be used alone or in a mixture with one another or with other active ingredients. Possibly other pesticides or pesticides may vary depending on the desired purpose can be added. If a broadening of the spectrum of activity other herbicides may also be added.
Beispielsweise eignen sich als herbizid wirksame Mischungspartner diejenigen Wirkstoffe, die in Weed Abstracts, Vol. 39, No. 1, 1990, unter dem Titel "List of common names and abbreviations employed for currently used herbicides ans plant growth regulators in Weed Abstracts" aufgeführt sind.For example, those suitable as herbicidally active mixture partners Active ingredients described in Weed Abstracts, Vol. 39, No. 1, 1990, under the title "List of common names and abbreviations employed for currently used herbicides ans 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 gegbenenfalls 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 therefore leave, if necessary a reduction 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 Minerale, zum Beispiel Bentonit, Silicagel, Talkum, Kaolin, Attapulgit, Kalkstein und pflanzliche Produkte, zum Beispiel Mehle.Minerals, 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, Formaldehydkonzentrate, 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 concentrates, fatty alcohol sulfates as well as substituted benzenesulfonic acids and their salts.
Der Anteil des, beziehungsweise der Wirkstoffe(s) in den verschiedenen Zubereitungen, kann in weiten Grenzen variieren. Beispielsweise enthalten die Mittel etwa 10 bis 90 Gewichtsprozent Wirkstoff, etwa 90 bis 10 Gewichtsprozent flüssige oder feste Trägerstoffe sowie gegebenenfalls bis zu 20 Gewichtsprozent oberflächenaktive Stoffe.The proportion of the active ingredient (s) in the various preparations can vary widely. For example, the Average about 10 to 90 percent by weight of active ingredient, about 90 to 10 percent by weight liquid or solid carriers and optionally up to 20 Weight percent surfactants.
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 Applikationen in Form von sogenannten Mikrogranulaten.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 applications in the form of so-called Microgranules.
Die Herstellung dieser Zubereitungen kann in an sich bekannter Art und Weise, zum Beispiel durch Mahl- oder Mischverfahren, durchgeführt werden. Gewünschtenfalls 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. If desired can only prepare the individual components 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 Dialkylnaphthalinsulfonat - 2.)
40 Gewichtsprozent Wirkstoff
25 Gewichtsprozent Kaolin
25 Gewichtsprozent kolloidale Kieselsäure
8 Gewichtsprozent Calciumsalz der Ligninsulfonsäure
2 Gewichtsprozent Natriumsalz der N-Methyl-N-oleyl-taurins
- 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 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
- 1.)
-
B) Emulsionskonzentrat
- 20 Gewichtsprozent Wirkstoff
75 Gewichtsprozent Isophoron
2 Gewichtsprozent ethoxyliertes Rizinusöl
3 Gewichtsprozent Calciumsalz der Dodecylbenzolsulfonsäure
- 20 percent by weight of active ingredient
75 weight percent isophorone
2% by weight of ethoxylated castor oil
3 weight percent calcium salt of dodecylbenzenesulfonic acid
- 20 Gewichtsprozent Wirkstoff
Die folgenden Beispiele erläutern die Herstellung der erfindungsgemäßen Verbindungen:The following examples illustrate the preparation of the invention Links:
5,94 g (33,5 mmol) 2-Hydrazino-3-trifluormethylpyridin werden mit 4,06 ml (33,5 mmol) Cyclohexancarbaldehyd in 120 ml Ethanol eine Stunde bei Raumtemperatur gerührt. Nach Abziehen des Lösungsmittels im Vakuum und Umkristallisieren des Rückstandes aus Hexan erhält man die Titelverbindung.5.94 g (33.5 mmol) of 2-hydrazino-3-trifluoromethylpyridine are mixed with 4.06 ml (33.5 mmol) cyclohexane carbaldehyde in 120 ml of ethanol for one hour at room temperature touched. After removing the solvent in vacuo and recrystallizing the residue from hexane gives the title compound.
Ausbeute: 7,69 g = 85% der Theorie
Fp.: 124-125°C
Yield: 7.69 g = 85% of theory
Mp .: 124-125 ° C
Analog zu Beispiel 1 wurden auch die folgenden erfindungsgemäßen Verbindungen hergestellt:The following compounds according to the invention were also analogous to Example 1 produced:
Die folgenden Beispiele erläutern die Anwendungsmöglichkeiten der erfindungsgemäßen Verbindungen:The following examples explain the possible applications of the compounds according to the invention:
Im Gewächshaus wurden die aufgeführten Pflanzenspezies vor dem Auflaufen mit den aufgeführten Verbindungen in einer Aufwandmenge von 1,0 kg Wirkstoff/ ha behandelt. Die Verbindungen wurden zu diesem Zweck als Emulsionen oder Suspensionen mit 500 Litern Wasser/ha gleichmäßig über den Boden versprüht. Hier zeigten drei Wochen nach der Behandlung die erfindungsgemäßen Verbindungen eine hohe Kulturpflanzenselektivität in Baumwolle 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 1.0 kg of active ingredient / ha treated. The compounds were used as emulsions for this purpose or suspensions with 500 liters of water / ha sprayed evenly over the soil. Here three weeks after the treatment showed the invention Compounds have a high crop selectivity in cotton with excellent Effect against weeds. The comparative did not show that equally high 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
ALOMY = Alopecurus myosuroides
IPOSS = Ipomoea pupurea
GOSHI = Gossypium hirsutum
ALOMY = Alopecurus myosuroides
IPOSS = Ipomoea pupurea
Im Gewächshaus wurden die aufgeführten Pflanzenspezies nach dem Auflaufen mit den aufgeführten Verbindungen in einer Aufwandmenge von 1,0 kg Wirkstoff/ ha behandelt. Die Verbindungen wurden zu diesem Zweck als Emulsionen oder Suspensionen mit 500 Litern Wasser/ha gleichmäßig über die Pflanzen versprüht. Hier zeigten zwei Wochen nach der Behandlung die erfindungsgemäßen Verbindungen eine hohe Kulturpflanzenselektivität in Baumwolle bei ausgezeichneter Wirkung gegen das Unkraut. Die Vergleichsmittel zeigten 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 / 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 two weeks after the treatment showed the inventive Compounds a high crop selectivity in cotton excellent action against weeds. The comparison means 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
ABUTH = Abutilon theophrasti
IPOSS = Ipomoea pupurea
MATCH = Matricaria chamomilla
GOSHI = Gossypium hirsutum
ABUTH = Abutilon theophrasti
IPOSS = Ipomoea pupurea
MATCH = Matricaria chamomilla
Im Gewächshaus wurden die in der Tabelle aufgeführten Verbindungen mit den ebenfalls erwähnten Aufwandmengen appliziert. Hierzu wurden die Wirkstoffe in Form von Zubereitungen auf die Wasseroberfläche in Gefäße mit 1500 ml Wasser pipettiert. Die Testpflanzenarten wurden im Vorauflauf und im 1- bis 5-Blatt-Stadium eingesetzt. Drei Wochen nach der Applikation wurde die Schädigung der Pflanzen bonitiert. Die erfindungsgemäßen Verbindungen zeigten eine starke Wirkung gegen wichtige Reisunkräuter bei gleichzeitiger Selektivität in Wasserreis.In the greenhouse, the compounds listed in the table with the applied application rates also mentioned. For this purpose, the active ingredients in the form of preparations on the water surface in vessels with 1500 ml Water pipetted. The test plant species were pre-emergence and 1- to 5-leaf stage used. Three weeks after the application, the Damage to plants rated. The compounds of the invention showed a strong effect against important rice weeds while at the same time Selectivity in water rice.
In der folgenden Tabelle bedeuten:In the following table mean:
0 = keine Schädigung
1 = schwache Schädigung
2 = mittlere Schädigung
3 = starke Schädigung
4 = total vernichtet0 = no damage
1 = slight damage
2 = moderate damage
3 = severe damage
4 = totally destroyed
ORYSA = Oryza sativa
ECHCG = Echinochloa crus-galli
MOOVA = Monocharia vaginalis
PASDS = Paspalum distichum
ORYSA = Oryza sativa
ECHCG = Echinochloa crus-galli
MOOVA = Monocharia vaginalis
PASDS = Paspalum distichum
Claims (5)
R¹ einen C₁-C₁₀-Alkylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl, Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄-alkyl- C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl, Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄-Alkyl- C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl oder Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₁-C₁₀-Alkylrest, einen C₂-C₁₀-Alkenylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl, Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄-alkyl- C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl, Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄-Alkyl- C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl oder Cyano- C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₂-C₁₀-Alkenylrest; einen C₂-C₁₀-Alkinylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl, Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄- alkyl-C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl, Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄- Alkyl-C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl oder Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₂-C₁₀-Alkinylrest, einen C₃-C₈-Cycloalkylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₁-C₄-Alkyl, Halogen-C₁-C₄-alkyl, Cyano- C₁-C₄-alkyl, C₂-C₄-Alkenyl, Halogen-C₂-C4-alkenyl, Cyano-C₂-C₄-alkenyl, C₂-C₄-Alkinyl, Halogen-C₂-C₄-alkinyl oder Cyano-C₂-C₄-alkinyl substituierten C₃-C₈-Cycloalkylrest, einen C₃-C₈-Cycloalkenylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₁-C₄-Alkyl, Halogen-C₁-C₄-alkyl, Cyano-C₁-C₄-alkyl, C₂-C₄-Alkenyl, Halogen-C₂-C₄- alkenyl, Cyano-C₂-C₄-alkenyl, C₂-C₄-Alkinyl, Halogen-C₂-C₄-alkinyl oder Cyano-C₂-C₄-alkinyl substituierten C₃-C₈-Cycloalkenylrest, einen Phenylrest oder einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Hydroxy, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, Halogen- C₁-C₄-alkoxy, Mercapto, C₁-C₄-Alkylthio, Halogen-C₁-C₄-alkylthio, C₁-C₄-Alkylsulfinyl, C₁-C₄-Alkylsulfonyl, C₁-C₄-Alkoxycarbonyl, Phenyl, Amino, C₁-C₄-Alkylamino, Di-C₁-C₄-Alkylamino, Cyano, Nitro, Methylendioxy, Ethylendioxy oder Isopropylidendioxy substituierten Phenylrest,
R² 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,
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 und
R⁵ Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Akoxy, 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
bedeuten.1. Agents with herbicidal activity, characterized by a content of a substituted N '- (2-pyridyl) aldehyde hydrazone of the general formula I. in the
R¹ is a C₁-C₁₀ alkyl radical, one or more, the same or different, by halogen, cyano, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₄-alkyl- C₃-C₆-cycloalkyl, halogen-C₁-C₄-alkyl- C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, cyano- C₃-C₆-cycloalkenyl, C₁-C₄-alkyl-C₃-C₆-cycloalkenyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl-substituted C₁-C₁₀- Alkyl radical, a C₂-C₁₀ alkenyl radical, one or more, the same or different by halogen, cyano, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₄-alkyl -C₃-C₆-cycloalkyl, halogen-C₁-C₄-alkyl- C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, cyano -C₃-C₆-cycloalkenyl, C₁-C₄-alkyl- C₃-C ₆-cycloalkenyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituted C₂-C₁₀ alkenyl; a C₂-C₁₀ alkynyl radical, one or more, identical or different by halogen, cyano, C₃-C--cycloalkyl, halogen-C₃-C--cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃ -C₆-cycloalkyl, halogen-C₁-C₄- alkyl-C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, cyano-C₃ -C₆-cycloalkenyl, C₁-C₄- alkyl-C₃-C₆-cycloalkenyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituted C₂-C₁₀ alkynyl , a C₃-C₈-cycloalkyl radical, one or more, identical or different by halogen, cyano, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkenyl, Halogen-C₂-C4-alkenyl, cyano-C₂-C₄-alkenyl, C₂-C₄-alkynyl, halogen-C₂-C₄-alkynyl or cyano-C₂-C₄-alkynyl substituted C₃-C₈-cycloalkyl radical, a C₃-C₈-cycloalkenyl radical , one or more, the same o the different by halogen, cyano, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkenyl, halogen-C₂-C₄-alkenyl, cyano-C₂-C₄-alkenyl , C₂-C₄-alkynyl, halogen-C₂-C₄-alkynyl or cyano-C₂-C₄-alkynyl substituted C₃-C₈-cycloalkenyl radical, a phenyl radical or one or more, the same or different, by halogen, hydroxy, C₁-C₄- Alkyl, C₁-C₄-alkoxy, halogen-C₁-Coxy-alkoxy, mercapto, C₁-C₄-alkylthio, halogen-C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkoxycarbonyl, Phenyl, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino, cyano, nitro, methylenedioxy, ethylenedioxy or isopropylidenedioxy substituted phenyl radical,
R² 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-C₁-alkylsulfonyl, C₁-C₆-alkoxycarbonyl, phenyl-C₁-C₆-alkoxycarbonyl, 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 and
R⁵ hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-acoxy, 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
mean.
R¹* einen C₁-C₁₀-Alkylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl, Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄-alkyl- C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl, Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄-Alkyl- C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkylC₃-C₆-cycloalkenyl oder Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₁-C₁₀-Alkylrest, einen C₂-C₁₀-Alkenylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl, Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄- alkyl-C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl, Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄- Alkyl-C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl oder Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₂-C₁₀-Alkenylrest, einen C₂-C₁₀-Alkinylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₃-C₆-Cycloalkyl, Halogen-C₃-C₆-cycloalkyl, Cyano-C₃-C₆-cycloalkyl, C₁-C₄-Alkyl-C₃-C₆-cycloalkyl, Halogen-C₁-C₄- alkyl-C₃-C₆-cycloalkyl, Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-Cycloalkenyl, Halogen-C₃-C₆-cycloalkenyl, Cyano-C₃-C₆-cycloalkenyl, C₁-C₄- Alkyl-C₃-C₆-cycloalkenyl, Halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl oder Cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituierten C₂-C₁₀-Alkinylrest, einen C₃-C₈-Cycloalkylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₁-C₄-Alkyl, Halogen-C₁-C₄-alkyl, Cyano- C₁-C₄-alkyl, C₂-C₄-Alkenyl, Halogen-C₂-C4-alkenyl, Cyano-C₂-C₄-alkenyl, C₂-C₄-Alkinyl, Halogen-C₂-C₄-alkinyl oder Cyano-C₂-C₄-alkinyl substituierten C₃-C₈-Cycloalkylrest, einen C₃-C₈-Cycloalkenylrest, einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Cyano, C₁-C₄-Alkyl, Halogen-C₁-C₄-alkyl, Cyano-C₁-C₄-alkyl, C₂-C₄-Alkenyl, Halogen-C₂-C₄- alkenyl, Cyano-C₂-C₄-alkenyl, C₂-C₄-Alkinyl, Halogen-C₂-C₄-alkinyl oder Cyano-C₂-C₄-alkinyl substituierten C₃-C₈-Cycloalkenylrest, einen Phenylrest oder einen ein- oder mehrfach, gleich oder verschieden durch Halogen, Hydroxy, C₁-C₄-Alkyl, Halogen-C₁-C₄-alkyl, C₁-C₄-Alkoxy, Halogen- C₁-C₄-alkoxy, Mercapto, C₁-C₄-Alkylthio, Halogen-C₁-C₄-alkylthio, C₁-C₄-Alkylsulfinyl, C₁-C₄-Alkylsulfonyl, C₁-C₄-Alkoxycarbonyl, Phenyl, Amino, C₁-C₄-Alkylamino, Di-C₁-C₄-Alkylamino, Cyano, Nitro, Methylendioxy, Ethylendioxy oder Isopropylidendioxy substituierten Phenylrest,
R²* 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, C₁-C₄-Alkylamino, Di-C₁-C₄-alkylamino oder Cyano, mit der Einschränkung, daß R²* nicht Brom ist, wenn R¹* Phenyl 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, Di-C₁-C₄- alkylamino, Cyano oder Nitro, mit der Einschränkung, daß R⁴* nicht Nitro ist, wenn R¹* Phenyl und R²* Methyl sind, und
R⁵* Wasserstoff, Halogen, Hydroxy, C₁-C₆-Alkyl, Halogen-C₁-C₆-alkyl, C₁-C₆- Akoxy, 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, mit der Einschränkung, daß R⁵* nicht Methyl ist, wenn R¹* Phenyl und R²* und R⁴* Chlor sind, bedeuten.4. Substituted N '- (2-pyridyl) aldehyde hydrazones of the general formula Ia in the
R¹ * is a C₁-C₁₀ alkyl radical, one or more, identical or different by halogen, cyano, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₁-alkyl -C₃-C₆-cycloalkyl, halogen-C₁-C₄-alkyl- C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, cyano -C₃-C₆-cycloalkenyl, C₁-C₄-alkyl- C₃-C₆-cycloalkenyl, halogen-C₁-C₄-alkylC₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituted C₁-C₁₀-alkyl radical , a C₂-C₁₀ alkenyl radical, one or more, identical or different by halogen, cyano, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₄-alkyl- C₃-C₆-cycloalkyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, cyano- C₃-C₆-cycloalkenyl, C₁-C₄- alkyl-C₃-C ₆-Cycloalkenyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituted C₂-C₁₀-alkenyl radical, a C₂-C₁ Alk-alkynyl radical, one or more times , identical or different by halogen, cyano, C₃-C₆-cycloalkyl, halogen-C₃-C₆-cycloalkyl, cyano-C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkyl, halogen-C₁-C₄- alkyl -C₃-C₆-cycloalkyl, cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, halogen-C₃-C₆-cycloalkenyl, cyano-C₃-C₆-cycloalkenyl, C₁-C₄- alkyl-C₃ -C₆-cycloalkenyl, halogen-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl or cyano-C₁-C₄-alkyl-C₃-C₆-cycloalkenyl substituted C₂-C₁₀-alkynyl radical, a C₃-C₈-cycloalkyl radical, a one or multiple, identical or different by halogen, cyano, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, cyano- C₁-C₄-alkyl, C₂-C₄-alkenyl, halogen-C₂-C4-alkenyl, cyano-C₂- C₄ alkenyl, C₂-C₄ alkynyl, halogen C₂-C₄-alkynyl or cyano-C₂-C₄-alkynyl substituted C₃-C₈-cycloalkyl radical, a C₃-C₈-cycloalkenyl radical, one or more, the same or different, by halogen, cyano, C₁-C₄-alkyl, halogen-C₁ -C₄-alkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkenyl, halogen-C₂-C₄-alkenyl, cyano-C₂-C₄-alkenyl, C₂-C₄-alkynyl, halogen-C₂-C₄-alkynyl or cyano -C₂-C₄-alkynyl-substituted C₃-C₈-cycloalkenyl, a phenyl radical or one or more, the same or different, by halogen, hydroxy, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, Halogen C₁-C₄-alkoxy, mercapto, C₁-C₄-alkylthio, halogen-C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkoxycarbonyl, phenyl, amino, C₁-C₄- Alkylamino, di-C₁-C₄-alkylamino, cyano, nitro, methylenedioxy, ethylenedioxy or isopropylidenedioxy substituted phenyl radical,
R² * 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, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino or cyano, with the restriction that R² * is not bromine when R¹ * is phenyl,
R³ * 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, with the restriction that R⁴ * is not nitro when R¹ * is phenyl and R² * is methyl, and
R⁵ * hydrogen, halogen, hydroxy, C₁-C₆-alkyl, halogen-C₁-C₆-alkyl, C₁-C₆-acoxy, 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, with the restriction that R⁵ * is not methyl when R¹ * is phenyl and R² * and R⁴ * are chlorine.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19904012040 DE4012040A1 (en) | 1990-04-11 | 1990-04-11 | 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 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19904012040 DE4012040A1 (en) | 1990-04-11 | 1990-04-11 | New triazolo-(4,3-a)pyridine(s) and N'-(2-pyridyl)-hydrazone(s) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4012040A1 true DE4012040A1 (en) | 1991-10-17 |
Family
ID=6404390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19904012040 Withdrawn DE4012040A1 (en) | 1989-11-30 | 1990-04-11 | New triazolo-(4,3-a)pyridine(s) and N'-(2-pyridyl)-hydrazone(s) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE4012040A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104892602A (en) * | 2015-06-16 | 2015-09-09 | 浙江工业大学 | Hydrazone derivative containing 1,2,4-triazole [4,3-a] pyridine ring as well as preparation and application of hydrazone derivative |
-
1990
- 1990-04-11 DE DE19904012040 patent/DE4012040A1/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104892602A (en) * | 2015-06-16 | 2015-09-09 | 浙江工业大学 | Hydrazone derivative containing 1,2,4-triazole [4,3-a] pyridine ring as well as preparation and application of hydrazone derivative |
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