EP1165515A1 - Diamides d'acide pyridin-2,3-dicarboxylique - Google Patents

Diamides d'acide pyridin-2,3-dicarboxylique

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Publication number
EP1165515A1
EP1165515A1 EP00925152A EP00925152A EP1165515A1 EP 1165515 A1 EP1165515 A1 EP 1165515A1 EP 00925152 A EP00925152 A EP 00925152A EP 00925152 A EP00925152 A EP 00925152A EP 1165515 A1 EP1165515 A1 EP 1165515A1
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European Patent Office
Prior art keywords
alkyl
halogen
methyl
alkoxy
chloro
Prior art date
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EP00925152A
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German (de)
English (en)
Inventor
Gerhard Hamprecht
Markus Menges
Olaf Menke
Robert Reinhard
Ingo Sagasser
Cyrill Zagar
Karl-Otto Westphalen
Martina Otten
Helmut Walter
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • 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
    • C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • 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

Definitions

  • the present invention relates to pyridine-2,3-dicarboxylic acid diamides of the general formula I
  • R 1 is halogen, CN, N0 2, C ⁇ -C 3 alkyl, C -C 3 haloalkyl, C ⁇ -C 3 -alkoxy, C 3 haloalkoxy, C ⁇ -C 3 alkylthio, C ⁇ -C3 haloalkylthio , C ⁇ -C 3 -alkylsulfinyl, C ⁇ -C 3 -haloalkylsulfinyl, C ⁇ -C 3 -alkylsulfonyl, C ⁇ -C 3 -haloalkylsulfonyl, C 3 -C 6 -cycloalkyl-, C 3 -C 6 -cycloalkyl-C ⁇ -C 3- alkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 3 -C 4 haloalkynyl, amino, C ⁇ -C 3 monoalkylamin
  • R 3 is halogen, CN, N0 2 , C ⁇ -C 3 alkyl, C ⁇ -C 3 alkoxy, C ⁇ -C 3 haloalkyl or C ⁇ ⁇ C 3 haloalkoxy;
  • R 4 is hydrogen, C ⁇ -C 3 alkyl, C ⁇ -C 3 haloalkyl, C ⁇ -C 3 alkoxy, saturated or unsaturated C 3 -C cycloalkyl, 3- bis
  • R 5 is hydrogen, C ⁇ -C 3 alkyl, OH or C ⁇ -C 4 alkoxy
  • R 6 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C ⁇ -C 6 cyanoalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl,
  • C 3 -C 6 cycloalkyl-C ⁇ -C 3 alkyl C 3 -C 6 cycloalkyl which has 1 or 2 substituents which are independently selected from halogen or C ⁇ -C 3 alkyl,
  • n 2 or 3 when Q is Q
  • the invention also relates to
  • herbicidal compositions which contain the compounds I as active substances,
  • EP 799 825 A describes certain pyridine-2,3-dicarboxylic acid diamides as herbicides.
  • the object of the present invention was to provide new herbicidally active pyridine-2,3-dicarboxylic acid diamides with which undesired plants can be controlled more effectively than with the known pyridine-2,3-dicarboxylic acid diamides.
  • the compounds of the formula I can contain one or more centers of chirality and are then present as enantiomers or diastereomer mixtures.
  • the invention encompasses both the pure enantiomers and the diastereomers and mixtures thereof.
  • the acid addition salts with those acids whose anions do not adversely affect the herbicidal activity of the compounds of the formula I are particularly suitable.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C ⁇ -C 4 -alkanoic acids, preferably formate , Acetate, propionate and butyrate. They can be formed by reacting the compounds of the formula I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the organic molecule parts mentioned in the definition of the substituents R 1 to R 6 or as residues on saturated cycloalkyl or saturated heterocyclic rings represent - like the meaning halogen - collective terms for individual lists of the individual group members.
  • All carbon chains that is to say all alkyl and alkenyl -, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cyanoalkyl, aminoalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkoxycarbonyl and alkoxycarbon etc.
  • Halogenated substituents preferably carry 1, 2, 3, 4 or 5 identical or different halogen atoms.
  • Halogen means fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine.
  • C ⁇ -C 3 alkyl methyl, ethyl, n-propyl, 1-methylethyl;
  • - C ⁇ -C 4 alkyl C ⁇ -C 3 alkyl as mentioned above, and n-butyl, 1-methylpropyl, 2-methylpropyl and 1, 1-dimethylethyl;
  • C ⁇ -C 6 alkyl C ⁇ -C-alkyl as mentioned above, and n-pentyl, 1-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1 , 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- Dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-l-methylpropyl and l-ethyl-2-methylpropyl;
  • (C ⁇ -C 3 alkyl) carbonyl methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl; in particular
  • C 2 -C 4 alkenyl eth-1-en-l-yl, prop-1-en-l-yl, prop-2-en-l-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methyl-prop-l-en-l-yl, 2-methyl-prop-l-en-l-yl, l-methyl-prop- 2-en-1-yl and 2-methyl-prop-2-en-1-yl;
  • C 3 -C 6 alkenyl C 3 -C alkenyl as mentioned above, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl-but-l-en-l-yl, 2-methyl-but-l-en-l-yl,
  • C 3 -C 6 alkynyl C 3 -C 6 -alkynyl as mentioned above, n-pent-1-yn-l-yl, n-pent-l-yn-3-yl, n-pent-l-yl 4-yl, n-pent-l-in-5-yl, n-pent-2-in-l-yl, n-pent-2-in-4-yl, n-pent-2-in-5- yl, 3-methyl-but-l-in-l-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1- in-l-yl, n-hex-l-in-3-yl, n-hex-l-in-4-yl, n-hex-l-in-5-yl, n-hex-l-in- 6-yl, n-hex-2-in-l-yl, n-
  • C ⁇ -C 6 alkoxy C ⁇ -C 3 alkoxy as mentioned above, and for example n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 0C (CH 3 ) 3 , n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy,
  • (C ⁇ -C 6 -alkoxy) carbonyl (C ⁇ -C 4 -alkoxy) carbonyl such as COOCH 3 , C00C 2 H 5 , n-propoxycarbonyl, C00CH (CH 3 ) 2 , n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl , C0O (CH 3 ) 3 , (C 4 -C 6 alkoxy) carbonyl such as n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl,
  • Cyano-C ⁇ -C 6 alkyl CH 2 CN, 1-cyanoeth-1-yl, 2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1 -yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-l-yl,
  • C 1 -C 6 haloalkyl or C 1 -C 3 haloalkyl C ⁇ -C 6 alkyl or C ⁇ -C 3 alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example chloromethyl , Dichloromethy1, trichloromethyl,
  • C 3 -C 4 haloalkenyl C 3 -C 4 alkenyl as mentioned above, partially or completely by fluorine, chlorine and / or
  • Bromine is substituted, for example 2-chloroallyl, 3-chloroallyl, 2,3-dichlorallyl, 3, 3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3- Bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromo-but-2-enyl, especially 2-chloroallyl or 3,3-dichloroallyl; C 3 -C 4 -haloalkynyl: C 3 -C 6 -alkynyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example 3-chloropropanol, 3-bromopropanol, 3-fluoropropyl, 3, 3, 3-trifluoropropargyl, 4-chloro-but-2-ynyl, 4-bro
  • haloalkoxy a C ⁇ -C 3 alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 0CH 2 F, 0CHF 2 , 0CF 3 , 0CH 2 C1 , 0CH (C1) 2 , 0C (C1) 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2,2, 2-trifluoroethoxy, 2 -Chlor-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, 0C 2 F 5 , 2-fluoropropoxy,
  • C 3 -C 4 alkenyloxy prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n- Buten-3-yloxy, 1-methyl-prop-l-en-l-yloxy,
  • 2-methyl-prop-1-en-1-yloxy 1-methyl-prop-2-en-1-yloxy, 2-methyl-prop-2-en-1-yloxy, preferably ethenyloxy and prop-2-ene -1-yloxy;
  • C ⁇ -C 6 -alkylthio-C ⁇ -C 6 -alkyl C ⁇ -C 6 -alkylthio substituted C ⁇ -C 6 -alkyl as mentioned above, for example for methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, (l-methylethylthio) methyl, n -Butylthiomethyl, (l-methylpropylthio) methyl, (2-methylpropylthio) methyl, (1, 1-dimethylethylthio) methyl1, 2- (methyl11hio) ethyl, 2- (ethylthio) ethyl, 2- (n-propylthio) ethyl, 2nd - (l-methylethylthio) ethyl, 2- (n-butylthio) ethyl,
  • C ⁇ -C 3 alkylthio SCH 3 , SC 2 H 5 , SCH 2 -C 2 H 5 and SCH (CH 3 ) 2 , in particular SCH 3 or SC 2 H 5 ;
  • C ⁇ -C 3 -haloalkylthio the same applies for C ⁇ -C 3 -haloalkyl and C ⁇ -C 3 -alkylthio;
  • C ⁇ -C 3 alkylsulfonyl methylsulfonyl, ethylsulfonyl, n-propylsulfonyl and 1-methylethylsulfonyl, especially methylsulfonyl or ethylsulfonyl; for C ⁇ -C 3 -haloalkylsulfonyl the same applies to C ⁇ -C 3 -haloalkyl and C ⁇ -C 3 -alkylsulfonyl;
  • C ⁇ -C 3 alkylsulfinyl methylsulfinyl, ethylsulfinyl, n-propylsulfinyl and 1-methylethylsulfinyl, especially methylsulfinyl or ethylsulfinyl; for C ⁇ -C 3 -haloalkylsulfinyl the same applies to C ⁇ -C 3 -haloalkyl and C ⁇ -C 3 -alkylsulfinyl; C ⁇ -C 4 alkoxy-C ⁇ -C 4 alkyl: by C Maschinen-C 4 alkoxy such as methoxy,
  • C ⁇ -C 4 alkyl for example CH 2 OCH 3 , CH 2 OC 2 H 5 , n-propoxymethyl,
  • C ⁇ -C 6 -alkoxy-C ⁇ -C 6 alkyl by C ⁇ -C 6 -alkoxy as mentioned above substituted C ⁇ -C 6 alkyl eg methoxymethyl, Ethoxymethy1, n-propoxymethyl, (1-methylethoxy) methyl, n, -Butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1, l-dimethylethoxy) methyl,
  • (C ⁇ -C 6 -alkoxy) carbonyl such as COOCH 3 , C00C 2 H 5 , n-propoxycarbonyl,
  • C ⁇ -C 2 alkyl for example CH 2 -C00CH 3 , CH 2 -C00C 2 H 5 , n-propoxycarbonylmethyl, CH 2 -C00CH (CH 3 ) 2 , n-butoxycarbonylmethyl, (l-methylpropoxycarbonyl) methyl,
  • C ⁇ -C 4 alkylcarbonyl acetyl, propionyl, butyryl, isobutyryl;
  • C ⁇ -C 4 -alkoximinomethyl methoxyimonomethyl, ethoxyiminomethyl, propoxyiminomethyl, isopropoxyiminomethyl, n-butoxyiminomethyl, sec. -Butoxyiminomethyl, isobutoxyiminomethyl, tert. -Butoxyiminomethyl;
  • (C ⁇ -C 6 alkoxy) carbonyl-C ⁇ -C 6 alkyl as mentioned above by (C ⁇ -C 6 alkoxy) carbonyl substituted C ⁇ -C6 alkyl, eg methoxycarbonylmethyl, ethoxycarbonylmethyl, 1- (methoxycarbonyl) ethyl , 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 3- (methoxycarbonyl) propyl, 4- (methoxycarbonyl) butyl, 5- (methoxycarbonyl) pentyl or 6- (methoxycarbonyl) hexyl;
  • C 3 -C 6 cycloalkoxy-C ⁇ -C 3 alkyl cyclopropyloxymethyl, cyclobutyloxymethyl, cyclopentyloxymethyl, cyclohexyloxymethyl, 1- (cyclopropyloxy) ethyl, l- (cyclobutyloxy) ethyl, l- (cyclopentyloxy) ethyl, 1- (cyclohexyloxy) ethyl , 2- (Cyclopropyloxy) ethyl, 2- (Cyclobutyloxy) ethyl1, 2- (Cyclopentyloxy) ethyl, 2- (Cyclohexyloxy) ethyl, 3- (Cyclopropyloxy) propyl, 3- (Cyclobutyloxy) propyl, 3- (Cyclopentyloxypropyl or 3- (Cyclohexyloxy) propyl, especially for Cyclopenty
  • C 3 -C 6 - or C 3 -C cycloalkyl cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl;
  • C 3 -C 6 cycloalkenyl l-cyclopropen-3-yl, l-cyclobuten-3-yl, l-cyclobuten-4-yl, l-cyclopenten-3-yl, l-cyclopenten-4-yl, l- Cyclohexen-3-yl or l-cyclohexen-4-yl;
  • saturated 3- to 7-membered heterocyclyl are: oxiranyl, thiiranyl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3- yl, tetrahydrothiophene-2-yl, tetrahydrothiophene-3-yl, l, 3-dioxolan-2-yl,
  • Examples of unsaturated 3- to 7-membered heterocyclyl are: oxirenyl, thiirenyl, oxet-3-yl, thiet-3-yl, 1, 2-dihydrofuran-2-yl, 1, 2-dihydrofuran-3-yl, 1, 2-dihydrothiophene-2-yl, 1,2-dihydrothiophene-3-yl, furan-2-yl, furan-3-yl, pyrrol-2-yl, pyrrol-3-yl, thiophene-2-yl, Thiophene-3-yl, 1,3-dioxol-2-yl, 1,3-oxathiol-2-yl, 1,3-dithiol-2-yl, 2,3-dihydropyran-4-yl, 2,3- Dihydropyran-5-yl, 2,3-dihydropyran-6-yl, 2,3-dihydrothiopyran-4-yl, 2,
  • pyridine-2,3-dicarboxamides according to the invention can be prepared by processes known per se from the literature, for example analogously to the synthetic routes described in EP 799 825. Reference is hereby made in full to EP 799 825.
  • the preferred manufacturing process involves reacting a pyridine-2,3-dicarboxylic anhydride compound of the formula
  • an inert solvent e.g. a chlorinated solvent, such as dichloromethane or 1,2-dichloroethane, an aromatic hydrocarbon, such as toluene or xylene, or an ether, such as diethyl ether, dioxane or tetrahydrofuran.
  • a chlorinated solvent such as dichloromethane or 1,2-dichloroethane
  • an aromatic hydrocarbon such as toluene or xylene
  • an ether such as diethyl ether, dioxane or tetrahydrofuran.
  • the reaction can take place over a wide temperature range, e.g. from room temperature to the boiling point of the solvent.
  • the solvents indicated above are suitable as inert solvents.
  • the amines of the formula Q-NH can also be reacted directly in the melt, preferably at 150 to 250 ° C., to give the imide.
  • a suitable oxidizing agent such as hydrogen peroxide or organic peracids, for example peracetic acid, m-chloroperbenzoic acid, see EP-A-799 825
  • pyridine-2,3-dicarboxylic acid anhydrides can be prepared by known processes, for example by treating the pyridine-2,3-dicarboxylic acids with phosgene in the presence of dimethylformamide by the process described in US Pat. No. 4,439,607.
  • R 21 C ⁇ -C 3 -alkoxymethyl, C ⁇ -C 3 -alkoximinomethyl, C ⁇ -C 3 -alkoxycarbonyl, C ⁇ -C 3 -alkylthiocarbonyl, C (0) NH 2 , CN, Cl, Br, C ⁇ -C 3 - Alkyl;
  • R 23 is hydrogen, C ⁇ -C 3 -alkoxymethyl, C ⁇ -C 3 -alkoxycarbonyl, C ⁇ -C 3 - alkylthiocarbonyl, C (0) NH 2 , CN, Cl, Br, C ⁇ -C 3 -alkyl, C ⁇ -C 3 - Alkoxy;
  • the anilines of formula 1 can be prepared by one of the following processes.
  • the isatoic anhydrides used as starting materials and their preparation are known per se and are known in the literature, e.g. Chem. Abstr. 75, 98482; 117, 233811; 125, 300514.
  • the 3-chloro-6-methyl-isatoic anhydride is described in more detail in the synthesis of the starting materials.
  • substituted anilines of the general formula Ia in which R 21 represents a C ⁇ -C 3 -alkoximinomethyl radical, are prepared by processes known per se, for example by using a substituted o-nitrobenzaldehyde of the formula 2
  • Suitable, nucleophilically displaceable leaving groups are halogen, preferably chlorine, bromine or iodine, C ⁇ -C 3 alkylsulfonyloxy such as methylsulfonyloxy, phenylsulfonyloxy, in which the phenyl radical is optionally substituted one or more times by halogen or C ⁇ -C 6 alkyl can be, such as phenylsulfonyloxy, p-toluenesulfonyloxy or p-Cl-phenylsulfonyloxy or a C ⁇ -C 3 -dialkylsulfate such as dimethyl or diethyl sulfate.
  • halogen preferably chlorine, bromine or iodine
  • C ⁇ -C 3 alkylsulfonyloxy such as methylsulfonyloxy
  • phenylsulfonyloxy in which the phenyl radical is optionally substituted one or more
  • the oxime ethers of the formula 6 can also be obtained by direct oximation of a substituted o-nitrobenzaldehyde 2 with a C ⁇ -C 3 alkoxyamine of the formula 7
  • substituted anilines of the formula Ib in which one of the radicals R 21 or R 23 represents a carboxylic acid function, are also prepared by processes known per se, for example by using a substituted aniline of the formula 8a or 8b
  • inert solvents whose boiling points are not below the boiling point of the resulting cleavage products
  • Diethyl glycol ether diethylene glycol dimethyl ether, tetraethyl urea, tetra butyl urea, dimethyl ethylene urea, dimethyl propylene urea, phthalic acid diethyl ether, phthalic acid diethylhexyl ester, octaethylene glycol or nonaethylene glycol, to the corresponding o-amino-15-benzonitriles of the form
  • the isatins of the formulas 10a or 10b can also be mixed with aqueous hydrogen peroxide in an aliphatic carboxylic acid, such as glacial acetic acid, in the presence of conc. Sulfuric acid to the isatoic anhydrides of the formulas 16a or 16b
  • the latter can be converted into the anthranil esters of the formulas 13a or 13b in an alternative reaction with C ⁇ -C 3 alkanols in the presence of a base compared to the corresponding reaction of the isatins 10a or 10b.
  • isatins required as further starting materials, for example the isatins 10az or 10bz, substituted anilines 8az or 8bz are reacted with chloral hydrate and hydroxylamine to give the corresponding isonitrosoacetanilides 9az or 9bz and cyclized with sulfuric acid according to the following scheme 2.
  • the synthesis of Isatinen is described for example in Beilstein, 21, I 402-405 and 21, I 5451.
  • the isatins lOaz or lObz can be converted, for example, by reaction with methanol in the presence of sodium methylate and aqueous hydrogen peroxide in anthranilic acid methyl ester 13az or 13bz according to Scheme 3.
  • the process is described in EP 32672 A.
  • R is, for example, a C ⁇ -C 3 alkyl radical and R 21 , R 22 and R 23 Cl, Br, C 2 -C 3 alkyl, R 21 and R 23 also CN or C ⁇ -C 3 alkoxycarbonyl or R 23 is also C ⁇ -C 3 alkoxy, for example after protecting the amino group with an acylating agent 30
  • R ' is a C ⁇ -C 4 alkyl radical and G represents a nucleophilic 35 displaceable leaving group (examples have already been mentioned above) to the acylanilines 19a or 19b
  • Me 1 or Me 111 each represent metals of the 1st or 3rd main group, reduce to the benzyl alcohols 21a or 21b,
  • anthranil esters 13a or 13b instead of the anthranil esters 13a or 13b, the corresponding anthranilic acids can also be used for the reduction.
  • acylanilines of the formulas 19c or 19d can also be used
  • R 2 and R 23 are Cl, Br, CN or C ⁇ -C 3 -alkoxycarbonyl and R 22 are Cl or Br, halogenate on the tolyl side chain to the benzyl halides 24c or 24d in which Hai is Cl or Br
  • R '"0H or alcoholate R'" 0Me wherein R '"stands for a C ⁇ -C 3 alkyl radical and Me for an alkali or alkaline earth metal atom, optionally in the presence of a base, to the benzyl ethers 22c or 22d
  • corresponding anthranil esters are used instead of the 19cz or 19dz nitriles, these are usually also saponified when the acylamino group is split off, so that they have to be esterified again, for example by refluxing in alcoholic hydrochloric acid with passage of hydrogen chloride gas.
  • Sodium, potassium, magnesium or calcium bicarbonate are suitable as alkali or alkaline earth bicarbonate.
  • the free hydroxylamine is added as an aqueous solution with stirring at 40 to 70 ° C, preferably 50 to 60 ° C, within 10 to 30 minutes to the solution of the nitrobenzaldehyde in an inert organic solvent and stirred for 1 to 4, preferably 2 to 3 hours at 50 ° C.
  • the molar ratio of starting material 2 to 7 is generally 0.9 to 1.2, preferably 0.95 to 1.1.
  • hydroxylamine hydrochloride can also be converted into the free base in an analogous manner and reacted with the aldehyde derivative 2 as described.
  • the oxime 4 obtained in this way must then be alkylated with an alkylating agent 5.
  • alkylating agent 5 are alkyl halides, e.g. Alkyl chlorides, bromides or iodides, dialkyl sulfates or aryl sulfonic esters are suitable.
  • the alkylating agent is expediently allowed to act on the oxime 5 in the presence of a base at 10 to 60 ° C., preferably 20 to 40 ° C., 0.5 to 5 h, in particular 1 to 2 h.
  • alkali metal or alkaline earth metal carbonates and alkali metal and alkaline earth metal hydroxides can be used as the base.
  • Alkali preferably stands for sodium and potassium, alkaline earth for magnesium and calcium.
  • the molar ratio of 4 to 5 is generally 0.9 to 1.4, preferably 1.1 to 1.2.
  • Analogous alkylations are described in Houben-Weyl, Methods of Organic Chemistry, IV Edition, Volume VI / 3, pp. 24-37.
  • the oxime ethers 6 thus obtained are then reduced with iron in the presence of an acid.
  • the oxime ether 6 is brought into a mixture of a carboxylic acid, such as acetic acid, and an alcohol, such as methanol, with a mixture of iron powder in the same mixture of carboxylic acid and alcohol for 2 to 6 h, advantageously 3 to 4 h, at 70 to 80 ° C in contact.
  • the reduction of oxime ether 6 can, however, also be carried out with hydrogen in the presence of a metal catalyst at 10 to 40 ° C.
  • the reduction can also be carried out under pressure in an autoclave, for example using Raney nickel. It is expedient to hydrogenate at 20 to 80 ° C., advantageously 40 to 60 ° C. and 1 to 50 bar, advantageously 10 to 20 bar hydrogen pressure.
  • Platinum, palladium, Raney nickel, Raney cobalt or also platinum oxide are suitable as metal catalysts. Suitable hydrogenation processes are described in Houben-Weyl, Methods of Organic Chemistry, IVth Edition, Volume 11/1, pp. 341-359.
  • the aniline 8 is expediently placed in water, then hydroxylammonium sulfate is added successively in portions, then conc. Add sulfuric acid and finally chloral with stirring at 20 to 40 ° C. The mixture is heated to 50 ° C. for 10 to 30 min and then adjusted by adding conc. Sodium hydroxide a pH of 1.5-2. After 6 to 16 h, advantageously 8 to 12 h at room temperature, the precipitate formed is isolated, taken up in a base, washed with a water-immiscible organic solvent and the isonitrosoacetanilide 9 is precipitated by adding an acid, e.g. Sulfuric acid.
  • an acid e.g. Sulfuric acid.
  • the starting materials 9 are treated for 2 to 5 hours at 60 to 90 ° C, advantageously 70 to 80 ° C with a strong acid, e.g. 90% sulfuric acid.
  • the synthesis of the starting materials 9 and 10 follows the manufacturing methods described in Beilstein, Volume 21, 402-405.
  • the isatins 10 are oxidized with hydrogen peroxide in the presence of alcohols 11 and alkali alcoholates 12 to give the anthranil esters 13.
  • aqueous hydrogen peroxide is added to the starting materials 10 in a mixture of an alcohol 9 and its alkali alcoholate with cooling added and treated for 20 to 60 min, advantageously 30 to 40 min at room temperature.
  • the molar amounts in which the starting materials are reacted 10 amount to 40 to 100, in particular 60 to 80 mol of alcohol, 1 to 5 mol, in particular 1 to 3 mol of alkali metal alcoholate and 1 to 3, in particular 1 to 1.5 mol, of hydrogen peroxide per mole of isatin 10.
  • the isatins 10 can also be used in the manner described in Scheme 1, and also according to J. Heterocycl. Chem. 1980, 20 17, 65 convert into their ß-oximes.
  • the isatins 10 are first oxidized with hydrogen peroxide in a carboxylic acid, such as acetic acid, as the reaction medium in the presence of catalytic amounts of sulfuric acid to give the isatoic anhydrides 16.
  • a carboxylic acid such as acetic acid
  • 35 is the Isatine 10 in acetic acid with (per mol Isatin 10) 4-8 ml, preferably 5-6 ml conc. Sulfuric acid and hydrogen peroxide and maintains the reaction temperature at 50-80 ° C, preferably 60-70 ° C.
  • the molar amounts of hydrogen peroxide per mol of isatin 10 are 0.95 to 1.3, preferably 1.0 to 1.15 mol.
  • the starting materials 16 are suspended in excess alcohol as the reaction medium, and 0.6 to 1 mol, preferably 0.7 to 0.9 mol, of an organic base, such as trie, thylamine, tri-n-propylamine, cyclohexyldimethylamine or N-methylmorpholine, added and treated for 1 to 5 h, preferably 2 to 3 h, at 50 to 80 ° C, preferably 60 to 70 ° C.
  • the anthranil esters 13 are obtained in a conventional manner.
  • 1 to 10 preferably 2 to 5, mol% of a highly nucleophilic organic base, such as 4-dimethylaminopyridine, can also be used as the catalyst.
  • the ring opening of the isatoic anhydrides 16 can also take place with ammonia to form the anthranilamides 17.
  • aqueous ammonia and compound 16 are brought into contact in a polar aqueous solvent, such as dimethylformamide, dimethylacetamide or N-methylpyrrolidone, at 70 to 95 ° C., advantageously 80 to 90 °.
  • the amount of ammonia, based on the starting material 16, is 0.95 to 1.3, preferably 1.1 to 1.2 mol.
  • the starting materials 17 are expediently treated in
  • Suitable acylating agents are chlorides or bromides of acetic acid, propionic acid, butyric acid, isobutyric acid or valeric acid, and also anhydrides
  • the acylating agent is expediently allowed to act on the anthranil ester in an inert solvent at 20 to 140 ° C., advantageously 80 to 120 ° C., within 4 to 20 h, advantageously 6 to 12 h.
  • the acid chloride is contacted with a mixture of the anthranile ester 13 and a base in an inert solvent at 10 to 60 ° C., advantageously 20 to 30 ° C., for 2 to 20 hours, advantageously 6 to 12 hours .
  • an inert solvent at 10 to 60 ° C., advantageously 20 to 30 ° C., for 2 to 20 hours, advantageously 6 to 12 hours .
  • ganic bases also pyridine, ⁇ -, ⁇ -, ⁇ -picoline, lutidine, quinoline or acridine can be used.
  • acid chlorides or bromides you can also in a two-phase system work that forms when water is used.
  • acylation can also be catalytically accelerated by highly nucleophilic bases such as p-dimethylaminopyridine or p-pyrrolidinopyridine.
  • the molar ratios in which the starting materials are reacted with one another are from 0.95 to 1.3, advantageously from 1.0 to 1.1, mol of acylating agent and base per mol of anthranil ester 13.
  • the catalyst is expediently used in an amount of 0 , 5 to 1.0, advantageously 1 to 3 mol% per mol of anthranil ester 13.
  • acylated anthranile ester 19 it is brought into an inert solvent with a complex metal hydride, such as sodium boranate, in one of the abovementioned solvents at 10 to 65 ° C., advantageously 20 to 50 ° C. for 2 to 10 h, advantageously 3 to 6 h Contact.
  • Suitable inert solvents are acetonitrile or aqueous alcohols (when using sodium boranate) or diisopropyl ether or tetrahydrofuran (when using lithium aluminum hydride or lithium boranate).
  • the molar ratios in which the starting materials are reacted with one another are from 0.5 to 3, advantageously 0.75 to 2.5, mol of lithium boranate per mol of starting material 20.
  • the starting materials 19 can also be advantageously treated by treatment with 0.95 to 1.1 mol, advantageously 1.0 to 1.03 mol, of aqueous alkali at 10 to 80 ° C., advantageously 20 to 60 ° C., for 1 to 10 hours Saponify at the ester group for 2 to 6 hours and then reduce as above with a complex metal hydride.
  • the procedure follows the procedure described in Organikum, VEB Deutscher Verlag dermaschineen, Berlin 1976, 15th edition, pp. 612-616.
  • the benzyl alcohols 21 are then alkylated by treatment with an alkylating agent 5.
  • the reaction is carried out under the same reaction conditions as for the alkylation of oxime 4 according to Scheme 1.
  • compound 22 is mixed with aqueous alkali, advantageously 0.95 to 1.2 mol, advantageously 1.0 to 1.1 mol, 1 to 12 h at 20 to 120 ° C., advantageously 2 to 8 h hydrolyzed at 60 to 100 ° C.
  • aqueous alkali advantageously 0.95 to 1.2 mol, advantageously 1.0 to 1.1 mol, 1 to 12 h at 20 to 120 ° C., advantageously 2 to 8 h hydrolyzed at 60 to 100 ° C.
  • the amount of chlorination reagent is 0.7 to 1.5, expediently 0.95 to 1.1 mol of chlorination reagent per mol of starting material 20.
  • the process is carried out at 10 to 200 ° C., advantageously 20 to 150 ° C. during 10 min to 10 h, advantageously 0.5 to 6 h.
  • an alkanol 11 and advantageously its alcoholate 12 are brought into contact with 30 14 at 10 to 100 ° C., advantageously 20 to 80 ° C. for 0.5 to 8 hours, advantageously 1 to 4 hours.
  • the alcoholate 12 one of the bases mentioned above or an alkali metal hydroxide in the alcohol in question can also be used.
  • the molar amounts in which the alcoholate 12 or the base is used are 0.95 to 1.2, advantageously 1.0 to 1.1 mol per mol of benzyl chloride 24.
  • the starting materials 22 are mixed with aqueous alkali (advantageously 0.95 to 1.2 mol, advantageously 1.0 to 1.1 mol) for 1 to 20 h, advantageously 2 to 10 h at 20 to 45 120 ° C. , advantageously treated 70 to 100 ° C. All of the reaction steps described above can be carried out without pressure or under pressure, continuously or batchwise.
  • the concentration of the starting materials in the solvent is 0.1 to 5 mol / 1, preferably 0.2 to 2 mol / 1.
  • reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or solvent extraction, or by removing the solvent and distilling or distributing the residue in a mixture of water and a suitable organic solvent and working up the organic phase towards the product.
  • the solvents used for the above reactions - depending on the temperature range - are hydrocarbons such as pentane, hexane, cyclopentane, cyclohexane, toluene, xylene, chlorinated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, 1, 1.2 , 2-tetrachloroethane, chlorobenzene, 1,2-, 1,3- or 1,4-dichlorobenzene, ethers such as 1,4-dioxane, tetrahydrofuran, anisole, glycol ethers such as dimethyl glycol ether, diethyl glycol ether, diethylene glycol dimethyl ether, esters such as ethyl acetate , Propyl acetate, methyl isobutyrate, isobutyl acetate, carboxamides such as dimethylformamide, N-methylpyrrolidone, nitrocarbons such
  • aniline compounds are accessible in good yields. They can also be produced on a larger scale. They are therefore particularly suitable as starting products for the preparation of compounds of the general formula I in which Q stands for appropriately substituted Qx.
  • R 1 is halogen, CN, N0 2 , C ⁇ -C 3 -alkyl, trifluoromethyl, C ⁇ -C 3 -alkoxy, C ⁇ -C 3 -haloalkoxy, C ⁇ -C 3 -alkylthio, trifluoromethylthio, difluoromethylthio, C--C 3 -alkylsulfinyl, Trifluoromethylsulfinyl, difluoromethylsulfinyl, C ⁇ -C 3 alkylsulfonyl, trifluoromethylsulfonyl, difluoromethylsulfonyl, cyclopropyl, amino or methylamino; and
  • R 3 is halogen, cyano, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy;
  • R 4 is hydrogen, C ⁇ -C 3 alkyl, C ⁇ -C 3 haloalkyl, C ⁇ -C 3 alkoxy, saturated C 3 -C cycloalkyl, 3- to 6-membered, saturated or unsaturated heterocyclyl, the 1 or 2 heteroatoms which are independently selected from N, O and S;
  • R 5 is hydrogen
  • R 6 C ⁇ -C 6 -alkyl, C ⁇ -C 6 -haloalkyl, C ⁇ -C 6 -cyanoalkyl, C 3 -C 6 -cycloalky1, C 3 -C 6 -cycloalkyl-C ⁇ -C 3 -alkyl, methyl-substituted C 3 - C 6 cycloalkyl, C ⁇ -C 4 alkoxy-C ⁇ -C 4 alkyl, methylthio-C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or together with R 5 a 5 - or 6-membered heterocycle, which has 1 or 2 heteroatoms, three are independently selected from N and 0, and optionally 1 or 2 substituents, which are independently selected from halogen, C ⁇ -C 3 alkyl or methoxy;
  • R 1 C ⁇ -C 3 alkyl, halogen, N0 2 , amino, mono-C ⁇ -C 3 alkylamino, C ⁇ -C 3 alkoxy or CN;
  • Q is one of the residues Qx to Q;
  • R 2 C ⁇ -C 3 alkyl, halogen, CN, carbamoyl, N0 2 , formyl, C ⁇ -C 4 alkylcarbonyl, C ⁇ -C 3 alkoximinomethyl,
  • R 3 C ⁇ -C 3 alkyl or halogen
  • R 4 is hydrogen, C ⁇ -C 3 alkyl, C ⁇ -C 3 haloalkyl, C 3 -C 6 cycloalkyl or 5- or 6-membered saturated or unsaturated heterocyclyl which has an oxygen heteroatom;
  • R 5 is hydrogen
  • R 6 is hydrogen, C ⁇ -C 6 alkyl, Cx-C ß- haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl-C ⁇ -C 3 alkyl;
  • R 2 for halogen, CN, carbamoyl, N0 2 , formyl, C ⁇ -C 3 -alkylcarbonyl, C ⁇ -C 3 -alkoximinomethyl, C ⁇ -C 3 -alkyl,
  • C ⁇ -C 3 -haloalkyl C -C 3 -alkoxy, C ⁇ -C 3 -haloalkoxy, C ⁇ -C 3 -alkoxy-methyl, C ⁇ -C 3 -alkoxycarbonyl, C ⁇ -C 3 -alkylthiocarbonyl or C ⁇ -C 3 -alkoxycarbonyl -C ⁇ -C 3 alkoxy, and
  • n stands for 2.
  • R 1 C ⁇ -C 3 alkyl, halogen, C ⁇ -C 3 alkoxy
  • R 2 C ⁇ -C 3 -alkyl, halogen, CN, carbamoyl, N0 2 , formyl, C ⁇ -C 3 -alkylcarbonyl, C ⁇ -C 3 -alkoximinomethyl, C ⁇ -C 3 -haloalkoxy, C ⁇ -C 3 -alkoxy, C ⁇ - C 3 -haloalkyl, C ⁇ -C 3 -alkoxymethyl, C ⁇ -C 3 -alkoxycarbonyl, C ⁇ -C 3 -alkylthiocarbonyl, C 3 -C 4 -alkynyloxy, C ⁇ -C 3 -alkylthio, C ⁇ -C 3 -alkoxycarbonyl- C ⁇ -C 3 alkoxy or C ⁇ -C 3 alkylsulfonyl, C ⁇ -C 3 haloalkylsulfonyl;
  • R 5 is hydrogen
  • R 6 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl-C ⁇ -C 3 alkyl;
  • R 3 C ⁇ -C 3 alkyl or halogen
  • R 5 is hydrogen
  • R 6 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl-C ⁇ -C 3 alkyl;
  • R 3 C ⁇ -C 3 alkyl or halogen
  • R 5 is hydrogen
  • R 6 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl-C ⁇ -C 3 alkyl;
  • R 4 is hydrogen, C ⁇ -C 3 alkyl, C ⁇ -C 3 haloalkyl, C 3 -C 6 cycloalkyl or 5- or 6-membered saturated or unsaturated heterocyclyl which has an oxygen heteroatom;
  • R 5 is hydrogen
  • R 6 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 cycloalkyl or C 3 -C6 cycloalkyl-C ⁇ -C 3 alkyl; X 0 or S;
  • R 2 C ⁇ -C 3 -alkyl, C ⁇ -C 3 -haloalkyl, C ⁇ -C 3 -alkoxy, C ⁇ -C 3 -alkoxycarbonyl, C ⁇ -C 3 -alkyl-thiocarbonyl, C ⁇ -C 3 -alkoxymethyl, C ⁇ - C 3 alkylthio, C ⁇ -C 3 alkylsulfonyl, halogen or CN, formyl or C ⁇ -C 3 alkoximinomethyl;
  • R 5 is hydrogen
  • R 6 is C ⁇ -C 6 alkyl or C 3 -C 6 cycloalkyl
  • R 1 halogen, CN, N0 2 , C ⁇ -C 3 alkyl, C ⁇ -C 3 haloalkyl, C ⁇ -C 3 alkoxy, C ⁇ -C 3 haloalkoxy, C ⁇ -C 3 alkylthio, C ⁇ -C 3 -Haloalkylthio, C ⁇ -C 3 -alkylsulfinyl, C ⁇ -C 3 -haloalkylsulfinyl, C ⁇ -C 3 -alkylsulfonyl, C ⁇ -C 3 -haloalkylsulfonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C ⁇ -C 3- alkyl, C 2 -C 4 -alkenyl, C 2 -C -haloalkenyl, C 2 -C 4 -alkynyl, C 3 -C 4 -haloalkynyl, amino, C ⁇
  • C ⁇ -C 3 -haloalkylsulfonyl at least one radical R 2 for formyl, carbamoyl, C ⁇ -C 4 -alkylcarbonyl, C ⁇ -C 3 -alkylthio-carbonyl, C ⁇ -C 3 -alkylcarbamoyl, C ⁇ -C 3 -alkoxymethyl, C ⁇ - C 3 -alkoxy-C ⁇ -C 3 -alkyl, C ⁇ -C 4 -alkoximinomethyl, C 3 -C 4 -alkenyloxy, C 3 -C 4 -haloalkenyloxy, C 3 -C 4 -alkynyloxy, C 3 -C -haloalkynyloxy, C ⁇ -C 3 -alkylthio, C ⁇ -C 3 -haloalkylthio, C ⁇ -C 3 -alkylsulfinyl, C ⁇ -C 3 -haloalkylsulfiny
  • R 5 is hydrogen, C ⁇ -C 3 alkyl, OH or C ⁇ -C alkoxy
  • R 6 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl,
  • Di-C ⁇ -C 4 alkylamino or R 6 together with R 5 is a 5- or 6-membered heterocycle of 1, 2 or 3 heteroatoms, which are selected independently of one another from N, 0 and S, and optionally 1 or 2 substituents which are independently selected from halogen or C ⁇ -C 3 alkyl, C ⁇ -C 3 alkoxy or C ⁇ -C 3 haloalkyl;
  • n 0, 1, 2 or 3;
  • R 1 particularly preferably represents halogen, in particular chlorine, C ⁇ -C 3 alkyl, in particular methyl and / or C ⁇ -C 3 alkoxy, in particular methoxy.
  • N is particularly preferably 2.
  • the radical R 1 is then in particular in the 5- and 6-position.
  • n is preferably 1.
  • R 2 particularly preferably represents CN, C ⁇ -C 3 -alkylcarbonyl, C ⁇ -C 3 -alkoxycarbonyl, C (0) NH 2 , CH 3 , CF 3 and / or halogen, in particular Cl. o is preferably 2 and R 2 is then in particular in the 2- and / or 3-position.
  • one of the radicals R 2 is preferably CN, carbamoyl, C ⁇ -C 3 -alkylcarbonyl, C ⁇ -C 3 -alkoxycarbonyl, C ⁇ -C 3 -alkoximino methyl, C ⁇ -C 3 -alkoxymethyl or formyl in the 2 position and the other radical for halogen, C ⁇ -C 3 alkyl or difluoromethoxy in the 3-position.
  • n is 2, particularly preferably 1 and o is 3.
  • one of the radicals R 2 is C ⁇ -C 3 -alkoxycarbonyl, C ⁇ -C 3 -alkoxymethyl, carbamoyl or cyano, preferably in the 2- Position.
  • the other radicals R 2 are preferably halogen and / or C ⁇ -C 3 alkyl, in particular in the 3- and / or 6-position.
  • the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control plant growth very well on non-cultivated areas, particularly when high amounts are applied. In crops like wheat, Rice, corn, soybeans and cotton act against weeds and grass weeds without causing any significant damage to crops. This effect occurs especially at low application rates.
  • the compounds I or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are suitable: Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassicus napus var. napus, Brassicus napus var. napobrassica, Brassica rapa var.
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active ingredients are less compatible for certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit wherever possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the compounds I or the herbicidal compositions comprising them can be, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkles or granules by spraying, atomizing, dusting, scattering or pouring.
  • directly sprayable aqueous solutions powders, suspensions, including high-strength aqueous oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkles or granules by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexane or strongly polar solvents, e.g. Amines such as N-methylpyrrolidone or water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alky
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oil dispersions the pyridine-2,3-dicarboxylic acid diamides, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • active substances, wetting agents, adhesives, dispersants or emulsifiers and, if appropriate, concentrates containing solvents or oils which are suitable for dilution with water can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the surface-active substances are the alkali, alkaline earth and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols as well as fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene ethyl, ethoxylated iso-phenylphenyl Octyl or nonylphenol,
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • the compounds I according to the invention can be formulated, for example, as follows:
  • I 20 parts by weight of compound no. 1 are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil.
  • aqueous dispersion which comprises 0.02% by weight of the active ingredient.
  • V 3 parts by weight of active ingredient No. 40 are mixed with 97 parts by weight of finely divided kaolin. You get on this
  • Wise a dust containing 3 wt .-% of the active ingredient.
  • VI 20 parts by weight of active ingredient No. 50 are intimately mixed with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.
  • VIII 1 part by weight of compound 72 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol EM 31 (non-ionic emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained.
  • Pyridine-2,3-dicarboxylic acid diamides are mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together.
  • 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides Aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het) -aryloxyalkanoic acid and its derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-l, 3-cyclohexanediones, hetaryl-aryl-ketones, benzylisoxazolidinones, meta-CF, 3- phenylderyl Carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1, 3-dione derivatives, diazines, dichloropropionic acid and their derivatives, chloroacetanilides, cyclohexane-1, 3-dione
  • the application rates of active ingredient are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, season, target plants and growth stage.
  • aqueous phase 5 was extracted once more with toluene.
  • the organic extracts were washed with water and dilute saline, dried over magnesium sulfate and concentrated in vacuo.
  • Example A7 Following the procedure of Example A4, the reaction of 5 g (27.1 mmol) of the compound from Example A5, 1.18 g (32.5 mmol) of hydrogen chloride in 100 ml of 1,2-dichloroethane, then 150 ml of phosphorous oxychloride 2.39 g (52.9% of theory) of the title compound as a yellowish powder, mp. 98-99 ° C.
  • Example A7 Following the procedure of Example A4, the reaction of 5 g (27.1 mmol) of the compound from Example A5, 1.18 g (32.5 mmol) of hydrogen chloride in 100 ml of 1,2-dichloroethane, then 150 ml of phosphorous oxychloride 2.39 g (52.9% of theory) of the title compound as a yellowish powder, mp. 98-99 ° C.
  • Example A7 Following the procedure of Example A4, the reaction of 5 g (27.1 mmol) of the compound from Example A5, 1.18 g (32.5 mmol
  • reaction mixture was concentrated in vacuo, stirred with ether / pentane and suction filtered, 0.2 g of N- (2-methyl-3-methylthiophenyl) 3-carboxy-6-methyl-pyridine-2-car- received bonklareamid of mp. 170-172 ° C. 1.64 g (13.78 mmol) of thionyl chloride were added to the filtrate with stirring at 22-28 ° C. and the mixture was stirred at 22 ° C. for a further 12 h. The reaction mixture was then added to 50 ml of ice water and the phases were separated. The organic phase was washed successively with saturated sodium bicarbonate solution and with brine.
  • Plastic pots with loamy sand with about 3.0% humus served as the culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the vessels were sprinkled lightly to promote germination and growth, and then plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, unless this was affected by the active ingredients.
  • test plants were first grown to a height of 3 to 15 cm, depending on the growth habit, and then treated with the active ingredients suspended or emulsified in water.
  • the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the application rate for the follow-up treatment was 0.5; 0.0625; 0.0313 or 0.0156 kg / ha a.S.
  • the plants were kept at 10-25 ° C and 20-35 ° C depending on the species.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to the individual treatments was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts, and 0 means no damage or normal growth.
  • the plants used in the greenhouse experiments are composed of the following types:
  • Table 7 Herbicidal activity in post-emergence applications in the greenhouse. Comparison of a compound according to the invention with compound no. 100 from EP 799 825.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Luminescent Compositions (AREA)
  • Indole Compounds (AREA)

Abstract

La présente invention concerne des diamides d'acide 2,3-dicarboxylique pyridine de formule (I) dans laquelle les variables ont les désignations spécifiées dans la description. Les composés peuvent être utilisés comme herbicides ou pour la déshydratation ou la défoliation de plantes.
EP00925152A 1999-03-31 2000-03-31 Diamides d'acide pyridin-2,3-dicarboxylique Withdrawn EP1165515A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19914721 1999-03-31
DE19914721 1999-03-31
PCT/EP2000/002899 WO2000058288A1 (fr) 1999-03-31 2000-03-31 Diamides d'acide pyridin-2,3-dicarboxylique

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EP1165515A1 true EP1165515A1 (fr) 2002-01-02

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EP00917030A Expired - Lifetime EP1165496B1 (fr) 1999-03-31 2000-03-31 Composes d'aniline substitues

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DOP2002000332A (es) * 2001-02-14 2002-08-30 Warner Lambert Co Inhibidores de piridina de metaloproteinasas de la matriz
AU2002366027B2 (en) 2001-11-21 2007-10-25 Sankyo Agro Company, Limited N-heteroarylnicotinamide derivatives
CA2854060A1 (fr) * 2011-11-03 2013-05-10 Bayer Intellectual Property Gmbh Benzoylamides a substitution ether d'oxime agissant comme herbicides
EP2797597B1 (fr) 2011-12-28 2020-02-26 Global Blood Therapeutics, Inc. Composés d'aldéhydes hétéroaryles substitués et leurs procédés d'utilisation dans l'accroissement de l'oxygénation tissulaire
CA3142817A1 (fr) 2011-12-28 2013-07-04 Global Blood Therapeutics, Inc. Composes benzaldehyde substitues et procedes d'utilisation de ceux-ci dans l'augmentation de l'oxygenation des tissus
US9458139B2 (en) 2013-03-15 2016-10-04 Global Blood Therapeutics, Inc. Compounds and uses thereof for the modulation of hemoglobin
US10100043B2 (en) 2013-03-15 2018-10-16 Global Blood Therapeutics, Inc. Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation
US10266551B2 (en) 2013-03-15 2019-04-23 Global Blood Therapeutics, Inc. Compounds and uses thereof for the modulation of hemoglobin
EP2970196B1 (fr) * 2013-03-15 2020-11-25 Global Blood Therapeutics, Inc. Composés et leurs utilisations pour la modulation de l'hémoglobine
EP3919056A1 (fr) 2013-03-15 2021-12-08 Global Blood Therapeutics, Inc. Composés et leurs utilisations pour la modulation de l'hémoglobine
AP2015008718A0 (en) 2013-03-15 2015-09-30 Global Blood Therapeutics Inc Compounds and uses thereof for the modulation of hemoglobin
US8952171B2 (en) 2013-03-15 2015-02-10 Global Blood Therapeutics, Inc. Compounds and uses thereof for the modulation of hemoglobin
EA201992707A1 (ru) 2013-11-18 2020-06-30 Глобал Блад Терапьютикс, Инк. Соединения и их применения для модуляции гемоглобина
EP3102208B1 (fr) 2014-02-07 2021-01-13 Global Blood Therapeutics, Inc. Polymorphe cristallin de la base libre de 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)méthoxy)benzaldéhyde
JP6452575B2 (ja) * 2015-08-19 2019-01-16 株式会社トクヤマ ミルタザピンの製造方法
WO2017096230A1 (fr) 2015-12-04 2017-06-08 Global Blood Therapeutics, Inc. Régimes posologiques pour 2-hydroxy-6-((2- (1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)méthoxy)benzaldéhyde
TWI752307B (zh) 2016-05-12 2022-01-11 美商全球血液治療公司 新穎化合物及製造化合物之方法
TW202332423A (zh) 2016-10-12 2023-08-16 美商全球血液治療公司 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑
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CN108947878B (zh) * 2018-07-24 2020-07-03 浙江中山化工集团股份有限公司 一种2-氯-6-甲硫基甲苯的制备方法
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ZA200108891B (en) 2003-01-29
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ZA200108931B (en) 2002-10-30
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CA2368451A1 (fr) 2000-10-05
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EA200100921A1 (ru) 2002-04-25
WO2000058288A1 (fr) 2000-10-05
SK13802001A3 (sk) 2002-06-04
HUP0200705A3 (en) 2002-12-28
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ATE244699T1 (de) 2003-07-15
MXPA01009733A (es) 2002-11-04
KR20020020685A (ko) 2002-03-15
CN1349507A (zh) 2002-05-15
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US6683213B1 (en) 2004-01-27
IL145565A0 (en) 2002-06-30
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