EP1047693A1 - Herbizide 3-(benzazol-4-yl)pyrimidindion-derivate - Google Patents

Herbizide 3-(benzazol-4-yl)pyrimidindion-derivate

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Publication number
EP1047693A1
EP1047693A1 EP98963564A EP98963564A EP1047693A1 EP 1047693 A1 EP1047693 A1 EP 1047693A1 EP 98963564 A EP98963564 A EP 98963564A EP 98963564 A EP98963564 A EP 98963564A EP 1047693 A1 EP1047693 A1 EP 1047693A1
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EP
European Patent Office
Prior art keywords
alkyl
carbonyl
butyl
ethyl
halogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98963564A
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German (de)
English (en)
French (fr)
Inventor
Robert Reinhard
Gerhard Hamprecht
Markus Menges
Olaf Menke
Peter Schäfer
Cyrill Zagar
Elisabeth Heistracher
Martina Otten
Helmut Walter
Karl-Otto Westphalen
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BASF SE
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BASF SE
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Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

Definitions

  • Herbicides 3 - (Benzazole - 4 -yD pyrimidinedione derivatives
  • the present invention relates to new 3- (benzazol-4-yl) pyrimidinedione derivatives of the formula I.
  • R 1 is hydrogen, amino, C ⁇ -Cg-alkyl or Ci-C ⁇ -haloalkyl
  • R 2 is hydrogen, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl,
  • R 3 is hydrogen, halogen or C ⁇ -Cg-alkyl
  • R 4 is hydrogen or halogen
  • R 5 cyano, halogen, Ci-Cg-alkyl, -C-C 6 haloalkyl, C ⁇ -C 6 alkoxy or Ci-Cg-haloalkoxy;
  • Ci-Cg-alkyl which by cyano, Ci-Cg-alkoxy, C ⁇ -C 6 -alkylthio, (C ⁇ -C 6 -alkoxy) carbonyl, (Ci-Cg-alkylamino) carbonyl, di (Ci-Cg-alkyl) aminocarbonyl or (Ci-Cg-alkyl) carbonyloxy may be substituted; l a chemical bond, oxygen, sulfur, -S (O) -, -S (0) 2 -, -NH- or -N (R 8 ) -;
  • R 7 and R 8 are independent of one another
  • each heterocyclyl ring can contain a carbonyl or thiocarbonyl ring member, and wherein each cycloalkyl, phenyl and heterocyclyl ring can be unsubstituted or can carry one to four substituents, each selected from the group consisting of cyano, nitro, amino, hydroxy, Carboxy, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy,
  • R 7 and R 8 together form a 1, 3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain, which are each unsubstituted or one to four C ⁇ -C 4 alkyl groups or one or two (C ⁇ -C 4 alkoxy ) can carry carbonyl groups;
  • the invention also relates to
  • WO 97/08170 describes certain 3 - (benz (ox / thi) azol-7-yl) -6- (trifluoromethyl) uracils as herbicides. Further 3- (benzthiazol -7-yl) uracils and their use as herbicides and for the desiccation / defoliation of plants are taught in WO 97/08171.
  • WO 97/12886 relates inter alia to certain 3-benzisoxazol-7 -yl-2, 4 - (1H, 3H) pyrimidinediones, which are said to have a herbicidal and desiccant effect.
  • the object of the present invention was to provide new herbicidally active uracil compounds which can be used to specifically control undesired plants better than the known ones.
  • herbicidal compositions which contain the compounds I and have a very good herbicidal action.
  • processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
  • the compounds of the formula I can contain one or more centers of chirality and are then present as mixtures of enantiomers or diastereomers.
  • E / Z isomers may also be possible.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • Agriculturally useful salts include, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I. So come as cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, as well as the ammonium ion, the one to four C ⁇ if desired -C 4 alkyl and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably
  • Tri (C ⁇ -C 4 alkyl) sulfonium and sulfoxonium ions preferably tri (C ⁇ -C alkyl) sulfoxonium, into consideration.
  • 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 von-C 4 -alkanoic acids, preferably Formate, acetate, propionate and butyrate. They can be formed by reacting I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • All carbon chains ie all alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, aminoalkyl, hydroxycarbonylalkyl, aminocarbonylalkyl, phenyl - alkyl, heterocyclylalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, Alkyl - sulfonyl, haloalkylsulfonyl, alkenyl, haloalkenyl, cyanoalkenyl, alkenyloxy, alkenylthio, alkenylsulfinyl, alkenylsulfonyl, alkynyl, haloalkynyl, cyanoalkynyl, alkynyloxy, alkynylthio, alkynylsulfinyl and
  • - C ⁇ -C 4 -haloalkyl for: a C ⁇ -C 4 -alkyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CH F, CHF, CF 3 , CHC1 , CH (C1), C (C1) 3 , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2, 2, 2- Trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, C 2 Fs, 2-fluoropropyl, 3- Fluoropropyl, 2,
  • Cx-C ß- alkyl for: a C ⁇ -C -alkyl radical as mentioned above, or for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n- Hexyl,
  • - C ⁇ -Cg-haloalkyl for: a C ⁇ -Cg-alkyl radical as mentioned above, which is partially or completely by fluorine, chlorine,
  • Bromine and / or iodine is substituted, for example one of the radicals mentioned under C ⁇ -C 4 -haloalkyl or for 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodine -l-pentyl, 5, 5, 5 -Tri - chloro-1-penyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6 -chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1 -hexyl, 6, 6, 6-trichloro-l-hexyl or dodecafluorohexyl;
  • Cyano -C ⁇ -C 4 alkyl for: CHCN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyanoprop-1-yl, 1-cyano-but -l-yl, 2-cyanobut-l-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, 3-cyanobut-2 -yl, 4-cyano-but-2-yl, 1- (CH 2 CN) eth-1-yl, 1- (CH 2 CN) -1 - (CH 3 ) -eth-l-yl or 1- ( CHCN) prop-1-yl;
  • Hydroxy-C ⁇ -C 4 -alkyl for: CH 2 OH, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxyprop-l-yl, 2-hydroxyprop-l-yl, 3-hydroxyprop-1-yl, 1 -hydroxybut - 1 -yl, 2 -hydroxybut - 1 -yl, 3 -hydroxybut - 1 -yl, 4-hydroxybut-l-yl, 1-hydroxybut-2 -yl, 2 -hydroxybut- 2 -yl, 3 -hydroxybut- 2 - yl, 4-hydroxybut-2-yl, 1- (CH 2 OH) eth-1-yl, 1- (CH 2 OH) -1- (CH 3 ) -eth-1-yl or 1- (CH 2 OH ) per -1-yl;
  • Amino-C ⁇ -C 4 -alkyl for: CH 2 NH, 1-aminoethyl, 2-aminoethyl, 1-aminoprop-l-yl, 2-aminoprop-l-yl, 3-aminoprop-1-yl, 1-amino- but-l-yl, 2-aminobut-l-yl, 3-aminobut-1-yl, 4-aminobut-1-yl, l-aminobut-2-yl, 2-aminobut-2-yl, 3-aminobut- 2-yl, 4-amino-but-2-yl, 1- (CH 2 NH 2 ) eth-1-yl, 1- (CH 2 NH 2 ) -1 - (CH 3 ) -eth-1-yl or 1- (CH 2 NH 2 ) prop -1-yl;
  • Heterocyclyl-C ⁇ -C-alkyl for: heterocyclylmethyl, 1-heterocyclic-ethyl, 2-heterocyclyl-ethyl, 1-heterocyclyl-prop-l-yl,
  • C ⁇ -C 4 -haloalkoxy for: a C ⁇ -C-alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, e.g. OCHF, OCHF, OCF 3 , 0CH 2 C1, OCH ( Cl) 2 , 0C (C1) 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2, 2, 2-trichloroethoxy, OC F 5 , 2-fluoropropoxy, 3-fluoropropoxy, 2,
  • - C ⁇ -Cg-alkoxy for: a C ⁇ -C 4 alkoxy radical as mentioned above, or for example n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2, 2-dimethylpropoxy, 1-ethylpropoxy, n -Hexoxy, 1,1-dimethylpropoxy, 1, 2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3 -Dimethylbutoxy, 2, 2-dimethylbutoxy,
  • - C ⁇ -Cg-haloalkoxy for: a C ⁇ -Cg-alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example one of the radicals mentioned under C ⁇ -C 4 -haloalkoxy or for 5 - fluorine-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5, 5, 5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluorine l-hexoxy, 6-chloro-l-hexoxy, 6-bromo-l-hexoxy, 6-iodo-l-hexoxy, 6,6,6-trichloro-1-hexoxy or dodecafluorohexoxy;
  • C ⁇ -C -haloalkylthio for: a C ⁇ -C 4 -alkylthio radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example SCH F, SCHF 2 , SCF 3 SCH 2 C1, SCH (C1) 2 , SC (C1) 3 , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2, 2, 2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, 2, 2, 2-t
  • - C ⁇ -C 6 -alkylthio for: a C ⁇ -C 4 -alkylthio radical as mentioned above, or for example n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dirnethylpropylthio, 1-ethyl- propylthio, n-hexylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1,2-di- methylbutylthio, 1, 3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2, 3-dimethylbutylthio, 3, 3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio
  • C ⁇ -C -alkoxy-C ⁇ -C 4 -alkyl for: C ⁇ -C 4 -alkoxy - as mentioned above - substituted C ⁇ -C 4 -alkyl, for example for CH 2 -OCH 3 , CH 2 -OC 2 H 5 , n-propoxymethyl, CH 2 -OCH (CH 3 ) 2 , n-butoxymethyl, (l-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH 2 -OC (CH 3 ) 3 , 2- (Methoxy) ethyl, 2- (ethoxy) ethyl, 2- (n-propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2- (l, l-dimethylethoxy) ethyl, 2- (methoxy) propyl
  • C ⁇ -C-haloalkoxy-C ⁇ -C 4 ⁇ alkyl for: C ⁇ -C 4 -haloalkoxy substituted as mentioned above C ⁇ -C 4 alkyl, for example for 2- (OCHF 2 ) ethyl, 2- (OCF 3 ) ethyl or 2- (OC 2 F 5 ) ethyl;
  • C ⁇ -C 4 -Alkylthio-C C-C -alkyl for: C ⁇ -C 4 -alkylthio - as mentioned above - substituted C C-C-alkyl, for example for CH 2 -SCH 3 , CH 2 -SC 2 H 5 , n-propylthiomethyl, CH 2 -SCH (CH 3 ) 2 , n-butylthiomethyl, (l-methylpropylthio) methyl, (2-methylpropylthio) methyl, CH 2 -SC (CH 3 ) 3 , 2- (methylthio) ethyl, 2- (ethylthio) - ethyl, 2- (n-propylthio) ethyl, 2- (1-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl, 2- (2 -Methyl-propyl,
  • C ⁇ -C4-haloalkylthio-C ⁇ -C 4 alkyl by C ⁇ -C 4 halo-alkylthio as mentioned above substituted C ⁇ -C4 alkyl, that is ethyl for example, 2- (SCHF 2), 2- ( SCF 3 ) ethyl or 2- (SC 2 F 5 ) ethyl;
  • C ⁇ -C 4 alkyl carbonyl for: C0-CH 3 , CO-C 2 H 5 , CO-CH 2 -C 2 H 5 , CO-CH (CH 3 ) 2 , n-butylcarbonyl, CO-CH (CH 3 ) -C 2 H 5 , CO-CH 2 -CH (CH 3 ) 2 or CO-C (CH 3 ) 3 , preferably for CO-CH 3 or CO-C 2 Hs;
  • (C ⁇ -C 4 -haloalkyl) carbonyl for: a (C ⁇ -C 4 -alkyl) carbonyl radical - as mentioned above - which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CO- CH 2 F, CO-CHF 2 , CO-CF 3 , C0-CH 2 C1, C0-CH (C1) 2 , C0-C (C1) 3 , chlorofluoromethylcarbonyl, dichlorofluoromethylcarbonyl, chlorodifluoromethylcarbonyl, 2-fluoroethylcarbonyl, 2- Chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2, 2, 2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2, 2-di
  • (C ⁇ -Cg-alkyl) carbonyl for: one of the abovementioned (Cx -C 4 alkyl) carbonyl radicals, or for example n-pentyl-CO, 1-methyl-butyl-CO, 2-methylbutyl -C0, 3-methylbutyl- CO, 2, 2-dimethylpropyl-CO, 1-ethylpropyl-CO, n-hexyl-CO, 1, 1-dimethylpropyl-CO, 1,2-dirnethylpropyl -C0, 1-methylpentyl-CO, 2-methylpentyl- CO, 3-methylpentyl-CO, 4-methylpentyl-CO, 1, 1-dimethylbutyl-CO, 1,2-dimethylbutyl-CO, 1, 3-dimethylbutyl -CO, 2, 2-dimethylbutyl - CO, 2,3-dimethylbutyl-CO, 3, 3-dimethylbutyl -CO, 1-ethylbutyl-
  • (C ⁇ -Cg-haloalkyl) carbonyl for: a (C ⁇ -Cg-alkyl) carbonyl radical - as mentioned above - which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CO-CH 2 F, CO-CHF 2 , CO-CF 3 , C0-CH 2 C1, C0-CH (C1) 2 , C0-C (C1) 3 , chlorofluoromethylcarbonyl, dichlorofluoromethylcarbonyl, chlorodifluoromethylcarbonyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbo- nyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethyl - __ carbonyl, 2, 2, 2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-ch
  • (C ⁇ -C-Alkyl) carbonyloxy for: 0-CO-CH 3 , 0-CO-C 2 H 5 , 0-CO-CH 2 -C 2 H 5 , 0-CO-CH (CH 3 ) 2 , 0 -CO-CH 2 -CH 2 -C 2 H 5 , O-CO-CH (CH 3 ) -C 2 H 5 , 0 0-CO-CH 2 -CH (CH 3 ) 2 or O-CO-C ( CH 3 ) 3 , preferably for 0-CO-CH 3 or 0-CO-C 2 H 5 ;
  • (C ⁇ -C haloalkyl) carbonyloxy for: a (C ⁇ -C 4 alkyl) carbonyl radical - as mentioned above - which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 0 -CO-CH 2 F, 0-CO-CHF 2 , 0-CO-CF 3 , 0-CO-CH 2 Cl, O-CO-CH (CD 2 , O-CO-C (CD 3 , chlorofluoromethylcarbonyloxy, dichlorofluoromethylcarbonyloxy , Chlorodifluoromethylcarbonyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethyl-0 carbonyloxy, 2-iodoethylcarbonyloxy, 2, 2-difluoroethylcarbonyloxy, 2,2, 2-trifluoroethylcarbonyloxy, 2-chloro-2
  • (C ⁇ -C-alkyl) carbonyloxy for: one of the above (C ⁇ -C 4 -alkyl) carbonyloxy radicals, or for example n-pentyl-COO,
  • (C ⁇ -C 6 alkyl) thiocarbonyl for: CS-CH 3 , CS-C 2 H 5 , CS-CH 2 -C 2 H 5 , CS-CH (CH 3 ) 2 , CS- (nC 4 H 9 ) , CS-CH (CH 3 ) -C 2 H 5 , CS-CH 2 -CH (CH 3 ) 2 , CS-C (CH 3 ) 3 , CS- (nC 5 H ⁇ ), CS-CH (CH 3 ) -CH 2 -C 2 H 5 , CS-CH 2 -CH (CH 3 ) -C 2 H 5 , CS-CH 2 CH 2 -CH (CH 3 ) 2 , CS-C (CH 3 ) 2 -C 2 H 5 , CS-CH (CH 3 ) -CH (CH 3 ) 2 , CS-CH 2 -C (CH 3 ) 3 , CS-CH (C 2 H 5 -C 2
  • (C ⁇ -C -alkoxy) carbonyl for: CO-OCH 3 , CO-OC 2 H 5 , CO-OCH 2 -C 2 H 5 , CO-OCH (CH 3 ) 2 , n-butoxycarbonyl, CO-OCH (CH 3 ) -C 2 H 5 , CO-OCH 2 -CH (CH 3 ) 2 or CO-OC (CH 3 ) 3 , preferably for CO-OCH 3 or CO-OC 2 H 5 ;
  • (C ⁇ -C 6 -alkoxy) carbonyl for: one of the above (C ⁇ -C-alkoxy) carbonyl radicals, or for example n-pentoxy-CO, 1-methylbutoxy-CO, 2-methylbutoxy-CO, 3-methylbutoxy- CO, 2, 2-dimethyl-propoxy-CO, 1-ethylpropoxy-CO, n-hexoxy-CO, 1, 1-dimethyl-propoxy-CO, 1, 2-dimethylpropoxy-CO, 1-methylpentoxy-CO, 2- Methylpentoxy-CO, 3-methylpentoxy-CO, 4-methylpentoxy-CO, 1,1-dimethylbutoxy-CO, 1, 2-dimethylbutoxy-CO, 1, 3-dimethylbutoxy-CO, 2, 2-dimethylbutoxy-CO, 2, 3-dimethylbutoxy-CO, 3, 3-dimethylbutoxy-CO, 1-ethylbutoxy-CO, 2-ethylbutoxy-CO, 1, 1, 2-trimethylpropoxy-CO, 1,2,2-trimethylpropoxy
  • (C ⁇ -Cg-Alkoxy) thiocarbonyl for: e.g. CS-OCH 3 , CS-OC 2 H 5 , CS-OCH 2 -C 2 H 5 , CS-OCH (CH 3 ) 2 , CS-0 (nC 4 H 9 ), CS-OCH (CH 3 ) -C 2 H 5 , CS-OCH 2 -CH (CH 3 ) 2 , CS-OC (CH 3 ) 3 , CS-0 (nC 5 H ⁇ ), CS-OCH (CH 3 ) -CH 2 -C 2 H 5 , CS-OCH 2 -CH (CH 3 ) -C 2 H 5 , CS-OCH 2 CH 2 -CH (CH 3 ) 2 , CO-OCH 2 -C (CH 3 ) 3 , CS- OCH (C 2 H 5 ) -C 2 H 5 , CS-0 (n-CgH 13 ), CS-
  • CO-SCH 3 CO-SC 2 H 5 , CO-SCH 2 -C 2 H 5 , CO-SCH (CH 3 ) 2 .
  • CO-SCH 2 CH 2 -C 2 H 5 CO-SCH (CH 3 ) -C 2 H 5 , CO-SCH 2 -CH (CH 3 ) 2 or CO-SC (CH 3 ) 3 , preferably for CO- SCH 3 or CO-SC H 5 ;
  • a C ⁇ -C -alkylsulf inyl for: a C ⁇ -C -alkylsulf inylrest such as SO-CH 3 , SO-C 2 H 5 , SO-CH 2 -C 2 H 5 , SO-CH (CH 3 ) 2 , SO - (nC 4 H 9 ), SO-CH (CH 3 ) -C 2 H 5 , SO-CH 2 -CH (CH 3 ) 2 or SO-C (CH 3 ) 3 , or for example SO- (nC 5 H ⁇ ), 1-methylbutyl-SO, 2-methylbutyl-SO, 3-methylbutyl-SO, 2,2-dryness thylpropyl-SO, 1-ethylpropyl-SO, n-hexyl-SO, 1,1-dimethylpropyl -SO, 1, 2-dimethylpropyl-SO, 1-methylpentyl-
  • C ⁇ -C 4 -alkylsulfinyl-C ⁇ -C 4 -alkyl for: C ⁇ -C 4 -alkylsulfinyl substituted as above-mentioned C ⁇ -C-alkyl, for example for CH 2 SOCH 3 , CH 2 SOC 2 H 5 , n- Propylsulfinylmethyl, CH 2 SOCH (CH 3 ) 2 , n-butylsulfinylmethyl, (1-methylpropylsulfinyDmethyl, (2-methylpropylsulfinyDmethyl, (1, 1-dimethylethylsulfinyl) methyl, 2-methylsulfinylethyl, 2-ethylsulfinylethyl, 2- (n-propylsulfinyl ethyl, 2- (1-methylethylsulfinyl) ethyl, 2- (n-butylsulfinyl) e
  • C ⁇ -C -haloalkylsulfinyl-C ⁇ -C 4 -alkyl for: C ⁇ -C -haloalkylsulfinyl substituted as mentioned above C -C -alkyl, for example for 2- (2, 2, 2-trifluoroethylsulfinyl) ethyl;
  • - C ⁇ -C 4 -haloalkylsulfonyl for: a C ⁇ -C 4 -alkylsulfonyl radical - as mentioned above - which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example S0 2 -CH 2 F, S0 2 - CHF 2 , S0 2 -CF 3 , S0 2 -CH 2 C1, S0 2 -CH (C1) 2 , S0 2 -C (C1) 3 , chlorofluoroethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl , 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2, 2-difluoroethy
  • S0 2 -CF 2 -C 2 F 5 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -2-chloroethylsulfonyl, 1- (bromomethyl) -2-bromethyl- sulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl, preferably for S0 2 -CHC1, S0 -CF 3 or 2, 2, 2-trifluoroethylsulfonyl;
  • C ⁇ -Cg-alkylsulfonyl for: a C ⁇ -C 4 -alkylsulfonyl radical as mentioned above, or for example S0 - (n-CsH ⁇ ), 1-methylbutyl-S0 2 , 2-methylbutyl - S0 2 , 3-methylbutyl - S0 2 , 2 , 2-Dirnethylpropyl - S0 2 , 1-ethylpropyl-S0 2 , n-hexyl-S0 2 , 1, 1-dimethylpropyl-S0 2 , 1,2-dimethylpropyl - SO2, 1-methylpentyl-S0 2 , 2- Methylpentyl-S0 2 , 3-methylpentyl-S0 2 , 4-methylpentyl-S0 2 , 1, 1-dimethylbutyl-S0 2 , 1,2-dirnethylbutyl -S0 2 , 1, 3-dimethylbutyl
  • C ⁇ -C 4 alkylsulfonyl-C ⁇ -C 4 alkyl by C ⁇ -C 4 alkylsulfonyl as mentioned above substituted C ⁇ -C4 alkyl, eg CH 2 S0 2 CH 3, CH 2 SO 2 -C 2 H 5 , CH 2 S0 2 -CH 2 -C 2 H 5 , CH 2 S0 2 -CH (CH 3 ) 2 , CH 2 SO 2 -CH 2 CH 2 -C 2 H 5 , (l-methylpropylsulfonyl) methyl , (2-MethylpropylsulfonyDmethyl, CH 2 S0 2 -C (CH 3 ) 3 , CH (CH 3 ) S0 2 -CH 3 , CH (CH 3 ) S0 2 -C 2 H 5 , CH 2 CH 2 S0 2 -CH 3 , CH 2 CH 2 SO 2 -C 2 H 5 , CH 2 CH 2 S0 2 -CH 2 -C 2 H 5 ,
  • C ⁇ -C 4 -alkylamino-C ⁇ -C -alkyl for: by C Maschinen-C 4 -alkylamino such as H 3 C-NH-, H 5 C 2 - H-, n-propyl-NH-, 1-methylethyl-NH -, n-Butyl- H-, 1-methylpropyl-NH-, 2-methylpropyl-NH- and 1, 1-dimethylethyl-NH-, preferably H 3 C-NH- or H 5 C 2 - H-, substi- tuiert C ⁇ -C 4 alkyl, for example for CH 2 CH 2 -NH-CH 3 , CH 2 CH 2 -N (CH 3 ) 2 , CH 2 CH 2 -NH-C 2 H 5 or CH 2 CH 2 - N (C 2 H 5 ) 2 ;
  • CO-NH-CH 3 CO-NH-C 2 H 5 , n-propyl - a ino, CO-NH-CH (CH 3 ) 2 , CO-NH- CH 2 CH 2 -C 2 H 5 , CO-NH-CH (CH 3 ) -C 2 H 5 , CO-NH-CH 2 -CH (CH 3 ) 2 or CO-NH-C (CH 3 ) 3 , preferably for CO-NH-CH 3 or CO-NH-C 2 H 5 ;
  • (C ⁇ -Cg-alkylamino) carbonyl for: one of the abovementioned (C ⁇ -C 4 -alkylamino) carbonyl radicals, or for example CO-NH- (n-CsH ⁇ ), 1-methylbutyl-NHCO-, 2-methylbutyl -NHCO-, 3-Methylbutyl-NHCO-, 2, 2-Dirnethylpropyl -NHCO-, 1-Ethylpropyl-NHCO-, CO-NH- (nC 6 H 13 ), 1,1-Dimethylpropyl-NHCO-, 1, 2-Dirnethylpropyl -NHCO -, 1-Methyl-pentyl-NHCO-, 2-methylpentyl-NHCO-, 3-methylpentyl-NHCO-, 4-methylpentyl-NHCO-, 1, 1-dimethylbutyl -NHCO-, 1, 2-dirnethylbutyl - NHCO -, 1, 3-D
  • (C ⁇ -C 4 -alkylamino) carbonyl-C ⁇ -C 4 -alkyl for: (C ⁇ -C 4 -alkylamino) carbonyl as mentioned above, preferably CO-NH-CH 3 or CO-NH-C 2 H 5 , substituted C ⁇ -C-alkyl, for example for CH 2 -CO-NH-CH 3 , CH 2 -CO-NH-C 2 H 5 , CH 2 -CO-NH-CH 2 -C 2 H 5 , CH 2 - CO-NH-CH (CH 3 ) 2 , CH 2 -CO-NH-CH 2 CH 2 -C 2 H 5 , CH 2 -CO-NH-CH (CH 3 ) -C 2 H 5 , CH 2 -CO -NH-CH 2 -CH (CH 3 ) 2, CH 2 -CO-NH-C (CH 3 ) 3 , CH (CH 3 ) -CO-NH-CH 3 , CH (CH 3 ) -CO-NH- C 2
  • Di (C ⁇ -C 4 alkyl) aminocarbonyl for: CO-N (CH 3 ) 2 , CO-N (C 2 H 5 ), CO-N (CH 2 -C 2 H 5 ) 2 , CO-N [CH (CH 3 ) 2 ] 2 , N, N-dibutylaminocarbonyl, CO-N [CH (CH 3 ) -C 2 H 5 ] 2, CO-N [CH 2 -CH (CH 3 ) 2 ] 2, CO-N [C (CH 3 ) 3] 2 , N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N- [CH (CH 3 ) 2 ] aminocarbonyl, N-butyl-N-methylamino - carbonyl, N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2-methylpropyl) aminocarbonyl, N- [C (CH 3 )
  • Di (C ⁇ -Cg-alkyl) aminocarbonyl for: one of the aforementioned di (C 1 -C 4 alkyl) aminocarbonyl radicals or, for example, N (CH 3 ) - (nC 5 H ⁇ ), N (C 2 H 5 ) - (nC 5 H ⁇ ), N (CH 2 -C 2 H 5 ) - (nC 5 H ⁇ ),
  • Di (C ⁇ -C 4 -alkyl) aminocarbonyl-C ⁇ -C-alkyl for: by di (C ⁇ -C 4 -alkyl) aminocarbonyl as mentioned above, preferably CO-N (CH 3 ) 2 or CO-N (C2H 5 ) 2 , substituted C ⁇ -C 4 alkyl, for example for CH 2 -CO-N (CH 3 ) 2 , CH 2 -CO-N (C 2 H 5 ) 2 , CH (CH 3 ) -CO-N (CH 3 ) 2 or CH (CH 3 ) -CO-N (C 2 H 5 ) 2 , preferably for CH 2 -CO-N (CH 3 ) 2 or CH (CH 3 ) -CO-N (CH 3 ) 2 ;
  • N-butyl-N- (2-methylpropyl) phosphonyl N-butyl-N- (1, 1-dimethylethyl) phosphonyl, N- (1-methylpropyl) -N- (2-methylpropyl) - phosphonyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) phosphonyl or N- (1, 1-dimethylethyl) -N- (2-methylpropyl) phosphonyl, preferably -PO (OCH 3 ) 2 or - PO (OC 2 Hs) 2 , substituted C 1 -C 4 alkyl, e.g.
  • CH 2 -PO (OCH 3 ) 2 CH 2 -PO (OC 2 H 5 ) 2 , CH (CH 3 ) -PO ( OCH 3 ) 2 or CH (CH 3 ) -PO (OC 2 H 5 ) 2 ;
  • haloalkenyl for: C 3 -Cg alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 2-chloroallyl, 3-chloroallyl, 2,3- Dichlorallyl, 3, 3-dichlorallyl, 2, 3, 3-trichlorallyl,
  • Cyano -C 3 -C 6 alkenyl for: for example 2-cyanoallyl, 3-cyanoallyl,
  • haloalkynyl for: C 3 -Cg alkynyl as mentioned above, partially or completely by fluorine, chlorine, bromine and / or
  • Iodine is substituted, e.g. 1, 1-difluoroprop-2-in-l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-l-yl, 1, 1-difluorobut-2-in-l- yl, 5-fluoropent-3-in-1-yl or 6-fluorohex-4-in-1-yl;
  • Cyano-C 3 -Cg-alkynyl for: for example 3-cyanopropargyl, 4-cyanobut-2-in-l-yl, 5-cyanopent-3 -in-l-yl and 6-cyanohex-4 -in-l-yl ;
  • C 3 -C 4 alkenyloxy-C ⁇ -C 4 alkyl for: by C 3 -C 4 alkenyloxy such as allyloxy, but-l-en-3-yloxy, but-l-en-4-yloxy, but-2 -en-l-yloxy, l-methylprop-2-enyloxy or 2-methylprop-2-enyloxy substituted C ⁇ -C 4 alkyl, for example for allyloxymethyl, 2-allyloxyethyl or but-l-en-4-yloxymethyl, in particular for 2-allyloxyethyl;
  • C 3 -C 4 alkynyloxy-C ⁇ -C 4 alkyl for: by C 3 -C 4 alkynyloxy such as propargyloxy, but-l-in-3-yloxy, but-l-in-4-yloxy, but-2 -in-1-yloxy, 1-methylprop-2-ynyloxy or 2-methylprop-2-ynyloxy, preferably propargyloxy, substituted C ⁇ -C alkyl, for example for propargyloxymethyl or 2-propargyloxyethyl, especially for 2-propargyloxyethyl;
  • C 3 -C 4 alkenylthio-C ⁇ -C alkyl for: by C 3 -C alkenylthio such as allylthio, but-l-en-3-ylthio, but-l-en-4-ylthio, but-2- en-l-yl-thio, l-methylprop-2-enylthio or 2-methylprop-2-enylthio substituted C ⁇ -C-alkyl, so for example for allylthio-methyl, 2-allylthioethyl or but-l-en-4-ylthiomethyl , especially for 2- (allylthio) ethyl;
  • C 3 -C 4 alkynylthio-C ⁇ -C 4 alkyl for: by C 3 -C 4 alkynylthio such as propargylthio, but-l-in-3-ylthio, but-l-in-4-ylthio, but- 2-in-l-ylthio, l-methylprop-2-inylthio or 2-methyl-prop-2-inylthio, preferably propargylthio, substituted C ⁇ -C 4 alkyl, for example for propargylthiomethyl or 2-propargylthioethyl, especially for 2- (propargylthio) ethyl;
  • C 3 -C 4 alkynylthio such as propargylthio, but-l-in-3-ylthio, but-l-in-4-ylthio, but- 2-in-l-ylthio, l-methylprop-2-inylthio or 2-methyl-prop-2-inylthio,
  • C 3 -C 4 alkenylsulfinyl-C ⁇ -C 4 alkyl for: by C 3 -C 4 alkenylsulfyl such as allylsulfinyl, but-l-en-3-ylsulfinyl, but-l-en-4-yl- sulfinyl, but-2-en-l-ylsulfinyl, l-methylprop-2-enylsulfinyl or 2-methylprop-2-enylsulfinyl substituted C ⁇ -C 4 ⁇ alkyl, for example for allylsulfinylmethyl, 2-allylsulfinylethyl or but-l-en- 4-ylsulfinylmethyl, especially for 2- (allylsulfinyl) ethyl;
  • C 3 -C 4 alkenylsulfyl such as allylsulfinyl, but-l-en-3-ylsulfin
  • C 3 -C 4 -Alkynylsulfinyl-C ⁇ -C 4 -alkyl for: by C 3 -C -alkynyl-sulfinyl such as propargylsulfinyl, but-l-in-3-ylsulfinyl, but-1- in-4-ylsulfinyl, but -2-in-l-ylsulfinyl, l-methylprop-2-inylsulfinyl or 2-methylprop-2-inylsulfinyl, preferably propargylsulfinyl, substituted C ⁇ -C 4 alkyl, for example for propargylsulfinylmethyl or 2-propargylsulfinylethyl, in particular for 2 - (propargylsulfinyl) ethyl;
  • C 3 -C -alkynyl-sulfinyl such as propargylsulf
  • C 3 -C 4 alkenylsulfonyl-C ⁇ -C 4 alkyl for: by C 3 -C alkenylsulfonyl such as allylsulfonyl, but-1-en-3-ylsulfonyl, but-1-en-4-yl-sulfonyl, But-2-en-l-ylsulfonyl, l-methylprop-2-enylsulfonyl or 2-methylprop-2-enylsulfonyl substituted C ⁇ -C 4 alkyl, e.g. for allylsulfonylmethyl, 2-allylsulfonylethyl or but-l-en- 4-ylsulfonylmethyl, especially for 2- (allylsulfonyl) ethyl;
  • C 3 -C 4 alkynylsulfonyl-C ⁇ -C 4 -alkyl for: by C 3 -C 4 -alkynylsulfonyl such as propargylsulfonyl, but-l-in-3-ylsulfonyl, but-l-in-4-ylsulfonyl, but -2-in-l-ylsulfonyl, l-methylprop-2-inylsulfonyl or 2-methylprop-2-inylsulfonyl, preferably propargylsulfonyl, substituted C ⁇ -C 4 alkyl, that is, for example, for propargylsulfonylmethyl or 2-propargylsulfonylethyl, in particular for 2 - (propargylsulfonyl) ethyl;
  • C 3 -C 4 -alkynylsulfonyl such as propargyls
  • cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;
  • C 3 -C 8 cycloalkyloxy-C ⁇ -C 4 alkyl for: cyclopropyloxymethyl, 1-cyclopropyloxy-ethyl, 2-cyclopropyloxy-ethyl, 1-cyclopropyl-oxy-prop-1-yl, 2-cyclopropyloxy-prop-l- yl, 3-cyclopropyloxy-prop-1-yl, 1-cyclopropyloxy-but-l-yl, 2-cyclopropyloxy-but-1-yl, 3-cyclopropyloxy-but-l-yl, 4-cyclopropyloxy-but-l- yl, l-cyclopropyloxy-but-2-yl, 2-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 4-cyclopropyl-oxy-but-2-yl, 1- (cyclopropyloxymethyl) -eth-l-
  • heterocycles with one to three heteroatoms selected from a group consisting of one to three nitrogen atoms, one or two oxygen and - one or two sulfur atoms.
  • saturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are: oxiranyl, thiiranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-1-yl, diaziridin-3-yl, oxetan-2- yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3- yl, tetrahydrothiophene-2-yl, tetrahydrothiophene-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1, 3-dioxolan-2-yl, 1, 3-dio
  • unsaturated heterocycles which may contain a carbonyl or thiocarbonyl ring member are: dihydrofuran-2-yl, 1, 2-oxazolin-3 -yl, 1, 2-oxazolin-5 -yl, 1, 3 -oxazolin- 2-yl;
  • heteroaromatics the 5- and 6-membered ones are preferred, e.g.
  • Furyl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrolyl such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as 2-oxazolyl, 4-0xazolyl and 5-oxazolyl, thiazolyl such as 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, Imidazolyl such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl such as 1, 2, 4-oxadiazol-3-yl,
  • All phenyl, carbocyclic and heteroeyclic rings are preferably unsubstituted.
  • R 1 is hydrogen, amino or C ⁇ -Cg-alkyl, in particular hydrogen or C ⁇ -C 4 -alkyl, particularly preferably hydrogen or methyl;
  • R 2 is hydrogen, halogen, C ⁇ -Cg-alkyl, C ⁇ -Cg-haloalkyl or C ⁇ -Cg-alkylsulfonyl, especially trifluoromethyl;
  • R 3 is hydrogen
  • R 4 is hydrogen, fluorine or chlorine
  • R 5 cyano or halogen, especially chlorine
  • R 6 C ⁇ -C 6 alkyl, C 3 -Cg alkenyl, C 3 -Cg alkynyl, Cx -Cg alkylsulfonyl, (C ⁇ -Cg alkyl) carbonyl, (C ⁇ -Cg alkyl) thiocarbonyl, (C ⁇ - Cg-alkoxy) carbonyl or C ⁇ -Cg-alkyl, which can be substituted by cyano, (C ⁇ -Cg-alkoxy) carbonyl, di (C ⁇ -Cg-alkyl) aminocarbonyl or (C ⁇ -Cg-alkyl) - carbonyloxy can, in particular C ⁇ -Cg-alkyl, C 3 -Cg-alkynyl, C ⁇ -Cg -alkylsulfonyl or (C ⁇ -C 6 -alkoxy) carbonyl.
  • L 1 represents a common leaving group such as halogen, preferably chlorine, bromine or iodine, (halogen) alkylsulfonyloxy, preferably methylsulfonyloxy or trifluoromethylsulfonyloxy, arylsulfonyloxy, preferably toluenesulfonyloxy, and alkoxysulfonyloxy, preferably methoxysulfonyloxy or ethoxysulfonyloxy.
  • halogen preferably chlorine, bromine or iodine
  • alkylsulfonyloxy preferably methylsulfonyloxy or trifluoromethylsulfonyloxy
  • arylsulfonyloxy preferably toluenesulfonyloxy
  • alkoxysulfonyloxy preferably methoxysulfonyloxy or ethoxysulfonyloxy.
  • an inert organic solvent for example in a protic solvent such as the lower alcohols, preferably in methanol or ethanol, if desired in a mixture with water, or in an aprotic solvent, e.g. in an aliphatic or cyclic ether such as methyl tert.
  • -butyl ether 1, 2-dimethoxyethane, tetrahydrofuran and dioxane, in an aliphatic ketone such as acetone, diethyl ketone and ethyl methyl ketone, in an amide such as dimethylformamide and N-methylpyrrolidone, in a sulfoxide such as dimethyl sulfoxide, in a urea such as tetramethyl urea and 1, 3 -Dimethyltetrahydro-2 (IH) pyrimidinone, in a carboxylic acid ester such as ethyl acetate, or in a halogenated aliphatic or aromatic hydrocarbon such as dichloromethane, dichloroethane, chlorobenzene and the dichlorobenzenes.
  • an aliphatic ketone such as acetone, diethyl ketone and ethyl methyl ketone
  • amide such as dimethylformamide
  • a base both inorganic bases, e.g. Carbonates such as sodium carbonate and potassium carbonate, hydrogen carbonates such as
  • Bases for example amines such as triethylamine, pyridine and N, N-diethylaniline, or alkali metal alcoholates such as sodium methoxide, sodium ethoxide and potassium tert. -butanolate are suitable.
  • reaction temperature is from 0 ° C to the boiling point of the reaction mixture, in particular from 0 to 60 ° C.
  • the salts of those compounds I in which R 1 is hydrogen can also be obtained in a manner known per se from the process products of methods C) to F).
  • the aqueous solution of an inorganic or organic base is mixed with the 3 - (benzazole-4-yDpyrimidinedione derivative I, in which R 1 is hydrogen.
  • the salt formation is then usually already at 20 to 25 ° C. with sufficient Speed.
  • the corresponding salt of 3 - (benzazol-4-yDpyrimidinedione derivative I can then be used, for example, by precipitation with a suitable inert solvent or by evaporation of the solvent can be isolated.
  • Salts of the 3 - (benzazole-4-yDpyrimidinedione derivatives I, the metal ion of which is not an alkali metal ion, can usually be prepared by salting the corresponding alkali metal salt in aqueous solution, as well as ammonium, Phosphonium, sulfonium and sulfoxonium salts using ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
  • 2,4-dinitrophenoxyamine has proven particularly useful as an amination reagent, however, e.g. hydroxylamine-O-sulfonic acid (HOSA) can also be used, which is already known from the literature as an amination reagent (cf. e.g.
  • HOSA hydroxylamine-O-sulfonic acid
  • the amination can be carried out in a manner known per se (see, for example, T. Sheradsky, Tetrahedron Lett. 1968, 1909; MP Wentland et al., J. Med. Chem. 22 (1984) 1103 and in particular EP-A 240 194, EP -A 476 697 and EP-A 517 181, where the amination of uracil is taught).
  • reaction is carried out in a polar solvent, e.g. in dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide or in ethyl acetate, which has so far proven to be particularly suitable.
  • a polar solvent e.g. in dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide or in ethyl acetate, which has so far proven to be particularly suitable.
  • Suitable bases are, for example, alkali metal carbonates such as potassium carbonate, alkali metal alcoholates such as sodium methylate and potassium tert. -butanolate or alkali metal hydrides such as sodium hydride.
  • the amount of base and aminating agent is preferably 0.5 to 2 times the molar amount, based on the amount of starting compound.
  • the sulfurization is usually carried out in an inert solvent or diluent, for example in an aromatic hydrocarbon such as toluene and the xylenes, in an ether such as diethyl ether, 1, 2-dimethoxyethane and tetrahydrofuran, or in an organic amine such as pyridine.
  • an inert solvent or diluent for example in an aromatic hydrocarbon such as toluene and the xylenes, in an ether such as diethyl ether, 1, 2-dimethoxyethane and tetrahydrofuran, or in an organic amine such as pyridine.
  • Phosphorus (V) sulfide and 2,4-bis (4-methoxyphenyl) -1,3,4,4-dithiadiphosphetane-2,4-dithione are particularly suitable as the sulfurization reagent.
  • the reaction temperature is normally 20 to 200 ° C, preferably 40 ° C to the boiling point of the reaction mixture.
  • L 2 means low molecular weight alkyl, preferably C ⁇ -C 4 alkyl, or phenyl.
  • cyclization is carried out in an inert organic solvent or diluent which is aprotic, for example in an aliphatic or cyclic ether such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, in an aromatic compound such as benzene and toluene or in a polar solvent such as dimethylformamide and dimethyl sulfoxide.
  • a polar solvent such as dimethylformamide and dimethyl sulfoxide.
  • polar solvent such as dimethylformamide and dimethyl sulfoxide
  • water can also be suitable as a diluent.
  • Suitable bases are preferably alkali metal alcoholates, in particular the sodium alcoholates, alkali metal hydroxides, in particular sodium hydroxide and potassium hydroxide, alkali metal carbonates, in particular sodium carbonate and potassium carbonate, and metal hydrides, in particular sodium hydride.
  • sodium hydride it has proven advantageous to work in an aliphatic or cyclic ether, in dimethylformamide or in dimethyl sulfoxide. Normally, 0.5 to 2 times the molar amount of base, based on the amount of IV or V, is sufficient for the reaction to succeed.
  • reaction temperature is from (-78) ° C to the boiling point of the respective reaction mixture, in particular from (-60) to 60 ° C.
  • R 1 in formula III or IV is hydrogen
  • the product of the process is obtained as a metal salt, the metal corresponding to the cation of the base used.
  • the ring closure reaction can be carried out by a method known per se (cf. e.g. Houben-Weyl, Methods of Organic Chemistry,
  • the reaction is preferably carried out in acidic, aqueous media, but lower carboxylic acids such as acetic acid are also suitable diluents.
  • Dilute mineral acids for example 10% hydrochloric acid, are particularly suitable as acidic aqueous solvents.
  • the nitrous acid is advantageously prepared in situ by adding an alkali metal nitrite - in bulk or in aqueous solution - to the reaction mixture consisting of the diaminobenzene in acidic aqueous solution or in a carboxylic acid.
  • a suitable reaction temperature is in particular 0 to 20 ° C., very particularly about 5 ° C.
  • the starting materials are expediently used in approximately stoichiometric amounts or one works with an excess of the theoretically expected amount of nitrous acid of not more than 10 mol%.
  • the condensation reaction of the bifunctional benzenes V with the carbonic acid or carboxylic acid derivatives are carried out in a manner known per se (see, for example, Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag Stuttgart, Vol. E8c, 1st Edition 1994, pp. 247- 284; Vol. E8b, 1st edition 1994, pp. 881-901; Vol. E8a, 1st edition 1993, pp. 1032-1078).
  • Preferred carbonic acid or carboxylic acid derivatives are the corresponding anhydrides, acid chlorides, orthoesters, diimides, nitriles, trichloromethyl-substituted compounds, isocyanates and their thio analogues.
  • Suitable solvents / diluents are, in particular, organic solvents, for example aromatic hydrocarbons such as benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane, lower alcohols such as methanol and ethanol, ali- phatic or cyclic ethers such as dimethoxyethane, tetrahydrofuran and dioxane, carboxylic acid esters such as ethyl acetate or aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide.
  • aromatic hydrocarbons such as benzene, toluene and o-, m-, p-xylene
  • halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane
  • lower alcohols such as methanol and ethanol
  • the reaction can be accelerated by adding catalytic amounts of an acid.
  • acids are mineral acids such as hydrochloric acids or sulfonic acids such as p-toluenesulfonic acid.
  • the amounts of acid are preferably 0.1 to 5 mol percent, based on the amount of V.
  • the reaction temperatures are preferably from 20 ° C. to the reflux temperature of the respective reaction mixture, in particular from 60 ° C. to the reflux temperature.
  • the carbonic acid or carboxylic acid derivative is used either in approx., Stoichiometric amount or in excess. In suitable cases, a very large excess can also be used or a solvent can be used. About stoichiometric amounts or an excess of up to 10 molar equivalents, based on the amount of V, are preferred.
  • the substituted 2 -aminophenols, -thiophenols and -anilines (V) are advantageously obtained by reducing the corresponding 2 -nitrophenols, -thiophenols or -anilines VIII (cf., for example, Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag Stuttgart, Vol. XI / 1, 4th edition 1957, p. 431ff.):
  • elemental metals such as iron, tin and zinc are used as reducing agents, Hydrogen in the presence of suitable catalysts such as palladium or platinum on carbon or Raney nickel, or complex hydrides such as LiAlH and NaBH 4 , if appropriate in the presence of catalysts.
  • Suitable solvents are usually - depending on the reducing agent - carboxylic acids such as acetic acid and propionic acid, alcohols such as methanol and ethanol, ethers such as diethyl ether, methyl tert. -butyl ether, tetrahydrofuran and dioxane, aromatics such as benzene and toluene, and mixtures of such solvents.
  • carboxylic acids such as acetic acid and propionic acid
  • alcohols such as methanol and ethanol
  • ethers such as diethyl ether, methyl tert. -butyl ether, tetrahydrofuran and dioxane
  • aromatics such as benzene and toluene, and mixtures of such solvents.
  • the reactions can be carried out at temperatures from (-100) ° C. to the boiling point of the respective reaction mixture.
  • the starting compounds are usually used in approximately stoichiometric amounts; in individual cases, however, an excess of one or the other component, up to about 10 mol%, can also be advantageous.
  • Protection usual protective group that protects phenols or thiophenols as ether or the amino group as amide.
  • the protective groups can be split off by methods known per se (cf., for example, Greene / Wuts: Protective Groups in Organic Synthesis, John Wiley & Sons, Inc., 2nd edition 1991, pp. 145ff. And pp. 279ff. ).
  • cleavage reagents for alkylphenols: trimethylsilyl iodide, boron tribromide,
  • Boron trichloride aluminum trichloride, lithium chloride or hydrogen bromide; in the case of optionally substituted benzylphenols or thiophenols: boron trifluoride, hydrofluoric acid or hydrogen / catalyst, preferably noble metal catalysts such as palladium or platinum.
  • the solvent / diluent should preferably be chosen so that it is inert to the particular cleaving reagent.
  • halides trimethylsilyl iodide, bortribromide, boron trichloride or aluminum trichloride, halogenated solvents such as dichloromethane, chloroform, carbon tetrachloride and dichloroethane are particularly preferred.
  • Hydrogen bromide is preferably used in aqueous solution, very particularly preferably as a 48% solution; Lithium chloride is preferably used in polar solvents such as lower alcohols, dimethyl sulfoxide and dimethylformamide; Hydrogenolytic methods are preferably carried out in lower alcohols or carboxylic acids, all with the addition of a hydrogen transfer agent such as cyclohexene and cyclohexadiene.
  • the temperature for the cleavage reaction is preferably from 0 ° C. to the boiling point of the respective reaction mixture.
  • the cleavage reagent is preferably used in approximately stoichiometric amounts or in excess.
  • the excess is particularly preferably between one and ten molar equivalents, based on the amount of IX.
  • the protected nitro compounds IX are finally obtainable in a manner known per se by nitrating (protected) phenols, thiophenols or anilines X (see, for example, Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag Stuttgart, Vol. 10/1, 1971, P. 479ff.):
  • nitrating acid mixed with sulfuric acid or acetic anhydride, or nitronium salts, especially nitronium tetrafluoroborate, are used as nitrating reagents. dress.
  • the mixture consisting of nitric acid and sulfuric acid, can consist of any proportions of the two mixing partners; preference is given to mixtures in which the sulfuric acid content is predominant or is used as a solvent. The same applies to the mixture of nitric acid and acetic anhydride.
  • Nitronium tetrafluoroborate is preferably used in aprotic, polar solvents, e.g. in acetonitrile or nitromethane.
  • the reaction temperature is generally from (-80) to 80 ° C, in particular (-20) ° C to 30 ° C.
  • the nitrations with the nitric acid reagent are preferably carried out with an approximately equimolar amount or particularly preferably with an excess of nitrating reagent.
  • the excess can be a multiple of the amount of X.
  • Nitronium tetrafluoroborate is preferably used in equimolar amounts to the substrate or in a small excess between 1.1 and 1.5 molar equivalents.
  • L 2 stands for low molecular weight alkyl, preferably C ⁇ -C 4 alkyl, or phenyl.
  • Suitable solvents or diluents are, in particular, water solvents which are azeotropically miscible with water, for example aromatics such as benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and chlorobenzene, aliphatic and cyclic ethers such as 1, 2 -Dimethoxyethane, tetrahydrofuran and dioxane, or cyclohexane, but also alcohols such as methanol and ethanol, into consideration.
  • aromatics such as benzene, toluene and o-, m-, p-xylene
  • halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and chlorobenzene
  • aliphatic and cyclic ethers such as 1, 2 -Dimethoxye
  • Suitable acidic catalysts are preferably strong mineral acids such as sulfuric acid and hydrochloric acid, phosphorus-containing acids such as orthophosphoric acid and polyphosphoric acid, organic acids such as p-toluenesulfonic acid and acidic cation exchangers such as "Amberlyst 15" (Fluka).
  • Suitable basic catalysts are, for example, alkali metal hydrides such as sodium hydride and particularly preferably alkali metal alcoholates such as sodium methoxide and ethanolate.
  • XIV and the ß-ketocarboxylic acid ester XIII are used in approximately stoichiometric amounts or one works with a slight excess of one or the other component, up to about 10 mol%.
  • reaction is carried out at a temperature of 60 to 120 ° C., for the rapid removal of water formed, preferably at the boiling point of the reaction mixture.
  • L 2 and L 3 each represent low molecular weight alkyl, preferably C ⁇ -C 4 alkyl, or phenyl.
  • the reaction is preferably carried out in an inert, water-miscible, organic solvent, for example an aliphatic or cyclic ether such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or a lower alcohol, in particular ethanol, the reaction temperature ture is normally 50 to 100 ° C, preferably at the boiling point of the reaction mixture.
  • an inert, water-miscible, organic solvent for example an aliphatic or cyclic ether such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or a lower alcohol, in particular ethanol
  • the reaction temperature ture is normally 50 to 100 ° C, preferably at the boiling point of the reaction mixture.
  • reaction can also be carried out in an aromatic diluent such as benzene, toluene and o-, m-, p-xylene, in which case the addition of either an acidic catalyst such as hydrochloric acid and p-toluenesulfonic acid or a base, e.g. an alkali metal alcoholate such as sodium methoxide and sodium ethanolate is recommended.
  • an acidic catalyst such as hydrochloric acid and p-toluenesulfonic acid or a base
  • an alkali metal alcoholate such as sodium methoxide and sodium ethanolate
  • the reaction temperature is normally 50 to 100 ° C., but preferably 60 to 80 ° C.
  • L 2 stands for low molecular weight alkyl, preferably C ⁇ -C 4 alkyl, or phenyl.
  • an essentially anhydrous aprotic organic solvent or diluent for example an aliphatic or cyclic ether such as diethyl ether, 1, 2-dimethoxyethane, tetrahydrofuran and dioxane, an aliphatic or aromatic hydrocarbon such as n-hexane, benzene, toluene and o-, m-, p-xylene, a halogenated, aliphatic hydrocarbon such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene, an aprotic, polar solvent such as dimethylformamide, hexamethylphosphoric triamide and dimethyl sulfoxide, or a mixture of the solvents mentioned.
  • an essentially anhydrous aprotic organic solvent or diluent for example an aliphatic or cyclic ether such as diethyl ether, 1, 2-dimethoxyethan
  • work can also be carried out in the presence of a metal hydride base such as sodium and potassium hydride or an organic tertiary base such as triethylamine and pyridine. the, wherein the organic base can simultaneously serve as a solvent.
  • a metal hydride base such as sodium and potassium hydride
  • an organic tertiary base such as triethylamine and pyridine.
  • the starting materials are expediently used in stoichiometric amounts or one works with a slight excess of one or the other component, up to about 10 mol%. If one works without solvent in the presence of an organic base, this is present in a large excess.
  • the reaction temperature is preferably (-80) to 50 ° C, in particular (-60) to 30 ° C.
  • the enamine ester III obtained is converted directly (i.e. "in situ") according to process D) into the corresponding product of value I using excess base.
  • L 2 and L 4 independently of one another represent low molecular weight alkyl, preferably C ⁇ -C 4 alkyl, or phenyl.
  • This reaction is advantageously carried out in an aprotic, polar solvent or diluent such as dimethylformamide, 2-butanone, dimethyl sulfoxide and acetonitrile, advantageously in the presence of a base, for example an alkali metal or alkaline earth metal alcoholate, in particular a sodium alcoholate such as sodium methoxide, an alkali metal or alkaline earth metal carbonates, in particular sodium carbonate, or an alkali metal hydride such as lithium and sodium hydride.
  • a base for example an alkali metal or alkaline earth metal alcoholate, in particular a sodium alcoholate such as sodium methoxide, an alkali metal or alkaline earth metal carbonates, in particular sodium carbonate, or an alkali metal hydride such as lithium and sodium hydride.
  • reaction temperature is generally 80 to 180 ° C, preferably at the boiling point of the reaction mixture.
  • a sodium alcoholate is used as the base and the alcohol formed in the course of the reaction is distilled off continuously.
  • the urethanes XIX are e.g. can be produced from carbonic acid chlorides XX and anilines XXI:
  • an auxiliary base such as triethylamine, pyridine or the alkali metal carbonates must generally be added to trap the hydrogen chloride formed in the reaction.
  • Pyridine is particularly suitable because it can also be used as a solvent.
  • the solvents / diluents used are in particular aromatic hydrocarbons such as benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane, lower alcohols such as methanol and ethanol, aliphatic or cyclic ethers such as dimethoxyethane , Tetrahydrofuran and dioxane, carboxylic acid esters such as ethyl acetate, or aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide.
  • aromatic hydrocarbons such as benzene, toluene and o-, m-, p-xylene
  • halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane
  • lower alcohols such as methanol and ethanol
  • aliphatic or cyclic ethers such as dimethoxye
  • the reaction temperature is generally from 0 ° C. to the reflux temperature of the respective reaction mixture.
  • the starting materials are expediently used either in approximately stoichiometric amounts or an excess of carbonic acid chloride of at most 10 mol percent is chosen.
  • the auxiliary base is usually used in an approximately equimolar amount, based on the amount of XX or XXI, or in excess up to about 2 times the molar amount. If pyridine is used as the auxiliary base, an even larger excess is recommended, in which case it is possible to work without additional solvent.
  • L 2 stands for low molecular weight alkyl, preferably C ⁇ -C 4 alkyl, or phenyl.
  • This reaction is expediently carried out in an essentially anhydrous, aprotic, organic solvent or diluent, for example in the presence of an aliphatic or cyclic ether such as diethyl ether, 1, 2-dimethoxyethane, tetrahydrofuran and dioxane, an aliphatic or aromatic hydrocarbon such as n-hexane, benzene , Toluene and o-, m-, p-xylene, a halogenated, aliphatic hydrocarbon such as methylene chloride, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene, an aprotic, polar solvent such as dimethylformamide, hexamethylphosphoric triamide and dimethyl sulfoxide, or a mixture of the mentioned solvents.
  • an aliphatic or cyclic ether such as diethyl ether, 1, 2-dimethoxyethane,
  • a metal hydride base such as sodium and potassium hydride, an alkali metal or alkaline earth metal alcoholate such as sodium methoxide, ethanolate and potassium tert. -butanolate, or an organic nitrogen base such as triethylamine and pyridine, where the organic base can simultaneously serve as a solvent.
  • a metal hydride base such as sodium and potassium hydride
  • an alkali metal or alkaline earth metal alcoholate such as sodium methoxide, ethanolate and potassium tert. -butanolate
  • an organic nitrogen base such as triethylamine and pyridine
  • the reaction temperature is generally from (-80) to 150 ° C, preferably from (-30) ° C to the boiling point of the reaction mixture.
  • arylanilides of formula IV are also new; they too can be prepared in a manner known per se, for example by reacting an amide XXIII with a urethane XXIV according to process M):
  • L 2 stands for low molecular weight alkyl, preferably C 1 -C 4 alkyl, or phenyl.
  • the reaction is advantageously carried out in a largely anhydrous solvent / diluent at atmospheric pressure, particularly preferably in the presence of an acid catalyst.
  • Suitable solvents / diluents are, in particular, water which is azeotropically miscible with water, for example aromatics such as benzene, toluene and o-, m-, p-xylene or halogenated hydrocarbons such as carbon tetrachloride and chlorobenzene.
  • Suitable catalysts are, in particular, strong mineral acids such as sulfuric acid, organic acids such as p-toluene sulfonic acid, acids containing phosphorus such as orthophosphoric acid and polyphosphoric acid or acidic cation exchangers such as "Amberlyst 15" (from Fluka).
  • reaction temperature of about 70 to 150 ° C is sufficient; To rapidly remove the water of reaction formed, however, it is expedient to work at the boiling point of the respective reaction mixture.
  • XXIII and XXIV are usually used in approximately stoichiometric amounts; XXIV is preferably used in a slight excess of up to about 20 mol%.
  • the amide XXIII can be prepared as follows (process N)):
  • the reaction is preferably carried out in an anhydrous, inert aprotic solvent, for example in a halogenated hydrocarbon such as methylene chloride, chloroform, carbon tetrachloride and chlorobenzene, an aromatic hydrocarbon such as benzene, toluene and o-, m-, p-xylene, or an aliphatic or cyclic ether such as Diethyl ether, dibutyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane.
  • a halogenated hydrocarbon such as methylene chloride, chloroform, carbon tetrachloride and chlorobenzene
  • an aromatic hydrocarbon such as benzene, toluene and o-, m-, p-xylene
  • an aliphatic or cyclic ether such as Diethyl ether, dibutyl ether, 1,2-dimethoxyethane,
  • the reaction temperature is generally about 70 to 140 ° C, especially 100 to 120 ° C.
  • XXV and XXI are usually used in approximately stoichiometric amounts, or one of the components is used in excess, up to about 10 mol%.
  • the isocyanates XVIII can be obtained, for example, from the aniline derivatives XXI according to process 0):
  • the process can be carried out in an inert, essentially anhydrous solvent or diluent or without solvent, the aniline derivatives XXI preferably being reacted with phosgene, a "phosgene equivalent” such as diphosgene, triphosgene and carbonyldiimidazole or with chloroformic acid trichloromethyl ester.
  • phosgene a "phosgene equivalent” such as diphosgene, triphosgene and carbonyldiimidazole or with chloroformic acid trichloromethyl ester.
  • Suitable solvents or diluents are, in particular, aprotic, organic solvents, for example dimethylformamide or aromatics such as toluene and o-, m-, p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane and chlorobenzene, aliphatic or cyclic ethers such as 1 , 2-dimethoxyethane, tetrahydrofuran and dioxane, or esters such as ethyl acetate, and mixtures of these solvents.
  • aprotic, organic solvents for example dimethylformamide or aromatics such as toluene and o-, m-, p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane and chlorobenzene, aliphatic or cyclic ethers such as 1 , 2-dimethoxyethan
  • the starting materials are expediently used in approximately stoichiometric amounts, or one of the components in excess, up to approximately 200 mol%.
  • the addition of a base such as triethylamine may be advantageous, for example in 0.5 to 2 times the molar amount, based on the amount of XXI.
  • the reaction temperature is generally from (-20) ° C to the reflux temperature of the particular solvent or reaction mixture.
  • aniline derivatives XXI are, in turn, in a manner known per se (see, for example, Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag Stuttgart, Vol. XI / 1, 4th edition 1957, p. 431ff.) By reducing the corresponding nitroderivate XXVI available:
  • Compounds XXVIII and XXI can also contain one or more centers of chirality and are then usually obtained as mixtures of enantiomers or diastereomers. If desired, the mixtures can be prepared by the usual methods, e.g. by means of crystallization or chromatography on an optically active adsorbate into which the largely pure isomers are separated. Pure optically active isomers can also be produced, for example, from corresponding optically active starting materials.
  • reaction mixtures are generally worked up by methods known per se, for example by diluting the
  • 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 vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, maize, soybeans and cotton, they work against weeds and grass weeds without causing any significant damage to crops. This effect occurs especially at low application rates.
  • the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the compounds I or the herbicidal compositions comprising them can be sprayed, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, and also high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, spreading agents or granules , Atomizing, dusting, scattering or pouring can be used.
  • 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.
  • inert auxiliaries mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated Benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, for example amines such as N-methylpyrrolidone and water.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons eg paraffins, tetrahydronaphthalene, alkylated naphthalenes and
  • Aqueous use forms can be prepared from emulsion concentrates, Sus pensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oil dispersions the substrates as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols as well as of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylpheny
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared 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, Urea 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 contain from about 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 active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with 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 as far as 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).
  • active ingredient I is 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (as), depending on the control target, season, target plants and growth stage.
  • active ingredient I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together.
  • reaction mixture was poured onto an ice-cold, saturated aqueous sodium chloride solution.
  • the solid product of value was then separated off, washed with water and dried in a drying cabinet at 20 ° C. under reduced pressure for several hours. Yield: 62.3 g;
  • Precursor 7.4 was reacted analogously to Example 5 with 3-amino-4,4,4,4-trifluoro-10-but-2-enoic acid ethyl ester.
  • the crude product was purified by means of medium pressure liquid chromatography (eluent:
  • Plastic flower pots with loamy sand with about 3.0% humus as substrate served as 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 pervaded 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 each according to the growth habit, only grown to a height of 3 to 15 cm and only 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 post-emergence treatment was 15.6 or 7.8 g / ha aS (active substance).
  • the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species.

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AU6018799A (en) 1998-09-09 2000-03-27 Ishihara Sangyo Kaisha Ltd. Fused-benzene derivatives useful as herbicides
JP2002529481A (ja) * 1998-11-16 2002-09-10 ビーエーエスエフ アクチェンゲゼルシャフト 除草剤３−［ベンゾ（オキサ／チア）ゾール−７−イル］−１ｈ−ピリミジン−２，４−ジオン類
DE19937772A1 (de) * 1999-08-10 2001-02-15 Bayer Ag Substituierte Heterocyclyl-2GH-chromene
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US7153583B2 (en) 2003-05-07 2006-12-26 Shin-Etsu Chemical Co., Ltd. Liquid silicone rubber coating composition and airbag
AU2005266622B8 (en) 2004-07-22 2011-05-19 Basf Aktiengesellschaft Method for the production of 3-phenyl(thio)uracils and dithiouracils
CN100398523C (zh) * 2005-06-13 2008-07-02 上海师范大学 2,4-二氯苯氧乙酰胺嘧啶衍生物及其制备方法和农药组合物
MX2012005501A (es) 2009-11-13 2012-07-10 Basf Se Compuestos 3- (3, 4- dihidro-2h-benzo [1, 4] -oxazin-6-il)-1h-piri midin-2, 4-diona como herbicidas.
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