Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
• • 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
• • 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
  • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
  • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
  • A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
  • C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
  • C07D273/04—Six-membered rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
  • C07D285/15—Six-membered rings
  • C07D285/16—Thiadiazines; Hydrogenated thiadiazines

Definitions

• the present invention relates to substituted ureas with a semicarbazide structure, in which the hydrazino group is incorporated into a 6-membered saturated heterocycle which has a further heteroatom which is not adjacent to the nitrogen atoms and is selected from oxygen and sulfur.
• the invention also relates to the use of such substituted ureas as herbicidal compositions which contain these compounds as active substances, and to processes for controlling unwanted vegetation with compounds of this type.
• J5 9082-372 describes herbicidally active tetrahydro-pyridazinecarboxylic acid derivatives and processes for their preparation.
• WO 94/10173 and German patent application P 198.29.745.9 describe herbicidally active bicyclic triazolinediones and processes for their preparation.
• substituted ureas of the formulas Ia and Ib have a particularly good herbicidal action.
• herbicidal compositions which contain the compounds Ia and Ib and which have a very good herbicidal action.
• processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I were found.
• the present invention relates to substituted ureas of the general formula Ia and Ib
• n 0, 1, 2 or 3;
• Q means one of the residues Ql to Q6:
• Y and Y ' are independently 0 or S;
• R 1 are hydrogen, C 6 alkyl, Ci-C ⁇ -haloalkyl, C -C 3 -alcohol xy-C ⁇ -C 3 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;
• R 2 Ci-Cö-alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 -allkynyl, C ⁇ -C 6 -haloalkyl, C ⁇ -C 6 -alkoxy-C ⁇ - C 6 -alkyl, hydroxy-carbonyl-C -C 6 -alkyl, Ci-Ce-alkoxycarbonyl-Cx-Cö-alkyl, C ⁇ -C 6 -alkylthio-C ⁇ -C 6 -alkyl, Ci-C ⁇ -alkylsulfinyl-C ⁇ - C 6 -alkyl, Ci-C ⁇ -alkylsulfonyl-Ci-Cö-alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl -CC 6 -alkyl, C 3 -C 6 -alkenyloxycarbonyl- -C
• R 3 is hydrogen or halogen
• R 4 C ⁇ -C 6 -alkyl, Cx-Cg-haloalkyl, 0CH 3 , SCH 3 , 0CHF 2 , halogen, cyano or N0 2 ;
• R 5 is hydrogen, hydroxy, mercapto, cyano, nitro, halogen, C ⁇ -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C ⁇ -C 6 haloalkyl, Ci-C ⁇ -Haloalkoxy, Ci-C ⁇ -haloalkylthio, C ⁇ -C 6 -alkoxy- (Cx-C ⁇ -alkyl) carbonyl, Ci-C ⁇ -alkylthio- (Ci-C ⁇ -alkyl) carbonyl, (Ci-C ⁇ -alkyl) - iminooxycarbonyl, C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxyamino-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkylamino-C ⁇ -C 6 -alkyl .
• Halogen nitro, cyano, hydroxy, C 3 -C 6 cycloalkyl, C ⁇ -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C ⁇ -C 5 -alkoxy-C ⁇ -C 6 -alkoxy, C ⁇ -C 6 -alkyl thio, C ⁇ -C 6 -alkylsulfinyl, C ⁇ -C 6 -alkylsulfonyl,
• Z 2 , Z 3 independently of one another represent oxygen or sulfur
• each cycloalkyl and heterocyclyl ring can contain a carbonyl or thiocarbonyl ring member and where each cycloalkyl and heterocyclyl ring can be unsubstituted or carry two, three or four substituents selected from cyano, Nitro, amino, hydroxy, halogen, C ⁇ -C-alkyl, C ⁇ -C 4 -haloalkyl, C ⁇ -C 4 -cyanoalkyl, C ⁇ -C 4 -hydroxyalkyl, C ⁇ -C 4 -aminoalkyl, C ⁇ -C 4 -alkoxy, C ⁇ -C 4
• R 7 is hydrogen, C ⁇ -C 6 -alkyl, C ⁇ -C 6 -haloalkyl, C ⁇ -C 3 -alkoxy-C ⁇ -C 3 -alkyl, C 2 -C 6 -cyanoalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 alkynyl;
• R 8 is hydrogen, C ⁇ -C 3 alkyl, C ⁇ -C 3 haloalkyl or halogen
• R 9 is hydrogen, C ⁇ -C 3 alkyl, C ⁇ -C 3 haloalkyl
• R 10 C ⁇ -C 15 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 10 alkenyl, C 3 -C 10 alkynyl, -C-C 6 -haloalkyl, C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkyl, -C-C 6 -alkylthio-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkylsulfinyl-C ⁇ -C 6 -alkyl, C -C 6 -alkylsulfonyl-C -C 6 -alkyl, C ⁇ -C 3 -alkoxy-C ⁇ -C 3 -alkoxy-C ⁇ -C 3 -alkyl, C 3 -C 6 -cycloalkyl-C ⁇ -C 6 -alkyl, carboxyl-Cx-C ⁇ -alkyl, C ⁇ -C 6 -Alkoxycarbonyl-C ⁇
• R 11 is hydrogen, C ⁇ -C 6 alkyl or C ⁇ -C 6 alkoxy
• R 12 hydrogen, C ⁇ -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C ⁇ -C 6 haloalkyl,
• the alkylene chain can additionally carry one to three halogen and / or cyano residues, phenyl or benzyl, which in adjacent positions can carry a divalent substituent such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy or one to five times by halogen, C ⁇ -C 4 alkyl , C ⁇ -C 4 -haloalkyl, C ⁇ -C -alkoxy, C ⁇ -C -haloalkoxy, C ⁇ -C 4 -alkylthio, C ⁇ -C 4 -haloalkylthio, amino, C ⁇ -C 4 -monoalkylamino, C
• R 13 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, hydroxy-C ⁇ -C 6 -alkyl, -CC 6 -alkoxy-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkylthio-C ⁇ -C 6 -alkyl, cyano-C ⁇ -C 6 -alkyl, (C ⁇ -C 6 -alkyl) carbonyl- C ⁇ -C 6 -alkyl, (C ⁇ -C 6 -alkoxy) carbonyl-C ⁇ -C 6 -alkyl, (C ⁇ -C 6 -alkoxy) -carbonyl-C 2 -C 6 -alkenyl, (C ⁇ -C 6 -Alkyl) carbonyloxy-C--C 6 -alkyl or phenyl
• R 14 is hydrogen, C ⁇ -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C ⁇ -C 6 alkoxy-C ⁇ -C 6 alkyl, ( C ⁇ -C 6 -alkoxy) -carbonyl-C ⁇ -C 6 -alkyl, (C 3 -C 6 -alkenyloxy) carbonyl- C ⁇ -C 6 -alkyl, phenyl or phenyl-C ⁇ -C 6 -alkyl, where the Phenyl ring of the latter two groups can be unsubstituted or can carry one or two radicals, selected from halogen, nitro, cyano, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C ⁇ -C 6 alkoxy and (C ⁇ -C 6 alkyl) carbonyl;
• R 14 has the meanings given for R 14 , except hydrogen
• R 15 is hydrogen, hydroxy, C -C6-alkyl, C 3 -C 6 cycloalkyl, C ⁇ -C 6 alkoxy, (CC 6 alkoxy) carbonyl-C ⁇ -C 6 alkoxy, C 3 -C 6 alkenyl or C 3 -C 6 alkenyloxy;
• R 16 is hydrogen, halogen, C ⁇ -C 6 -alkyl, C ⁇ -C 6 -haloalkyl, C ⁇ -C 6 -alkoxy, C ⁇ -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C ⁇ -C 6 alkylthio, C ⁇ -C 6 haloalkylthio,
• R 17 is hydrogen, cyano, C ⁇ -C 6 alkyl, C -C ⁇ haloalkyl,
• R 18 is hydrogen, hydroxyl, -CC 6 -alkyl, C 3 -C 6 -alkenyl,
• R 22 is hydrogen, 0-R 31 , SR 31 , C ⁇ -C 6 alkyl, which can also carry one or two C ⁇ -C 6 alkoxy substituents, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl , C ⁇ -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl-, C ⁇ -C 6 -alkylthio-C ⁇ -C 6 -alkyl, C -C 6 -alkyliminooxy, -N (R 27 ) R 28 or phenyl, which can be unsubstituted or carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ⁇ -C 6 alkyl, C 2 -C 6 alkenyl, C ⁇ -C 6 haloalkyl, C ⁇ -C 6 -Alkoxy and (C ⁇ -C 6 -alkoxy) carbonyl;
• R 23 is hydrogen, cyano, halogen, C ⁇ -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkyl, (C ⁇ -C 6 -Alkyl) carbonyl, (C ⁇ -C 6 -alkoxy) carbonyl, -N (R 27 ) R 28 or phenyl, which in turn can carry one to three substituents, selected from cyano, nitro, halogen, C ⁇ -C 6 -Al - kyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 alkenyl, C ⁇ -C 6 alkoxy and (C ⁇ -C 6 alkoxy) carbonyl;
• R 24 is hydrogen, cyano, halogen, C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxy, C -C 6 -haloalkyl, (C ⁇ -C 6 -alkyl) carbonyl or (C--C 6 -alkoxy) carbonyl ;
• R 25 is hydrogen, cyano, C ⁇ -C 6 alkyl or (C ⁇ -C 6 alkoxy) carbonyl;
• R 26 , R 31 independently of one another are hydrogen, C ⁇ -C 6 -alkyl,
• R 27 , R 28 , R 29 , R 3 ° independently of one another are hydrogen,
• C 1 -C 6 alkyl C 3 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C ⁇ -C 6 haloalkyl, C ⁇ -C 6 alkoxy-C ⁇ -C 6- alkyl, (C ⁇ -C 6 -alkyl) carbonyl, (C ⁇ -C 6 -alkoxy) carbonyl, (Cx-C ß -alkoxy) carbonyl-C ⁇ -C 6 -alkyl,
• (C ⁇ -C 6 -alkoxy) carbonyl-C 2 -C 6 -alkenyl in which the alkenyl chain can additionally carry one to three halogen and / or cyano residues, Cx-C ß -alkylsulfonyl, (C ⁇ - C 6 -alkoxy) carbonyl-C ⁇ -C 6 -alkylsulfonyl, phenyl or phenylsulfonyl, where the phenyl rings of the latter two radicals can be unsubstituted or in turn can carry one to three substituents, each selected from cyano, nitro, halogen, C ⁇ -C 6 -alkyl, C ⁇ -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C ⁇ -C 6 -alkoxy and (Ci-C ß -alkoxy) carbonyl; or
• R 29 and R 30 together with the common nitrogen atom for a saturated or unsaturated 4- to
• the compounds of the formulas Ia and Ib 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 Ia and Ib.
• cations in particular the ions of the alkali metals, preferably lithium, sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which if desired one to four C devis -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, preferably sulfoxonium Tri (C ⁇ -C 4
• Anions of usable 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 formulas Ia and Ib 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 R 1 to R 2 , R 4 to R 31 as well as on phenyl, cycloalkyl and heterocyclyl rings represent collective terms for individual enumeration of the individual group members.
• All carbon chains, that is to say all (optionally substituted) alkyl -, Alkenyl or alkynyl parts can be straight-chain or branched.
• Halogenated substituents preferably carry one to five identical or different halogen atoms. Halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
• - 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, that is, for. B. CH 2 F, CHF 2 , CF 3 , CH 2 CI, dichloromethyl, trichloromethyl, 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 F 5 , 2-fluoropropyl, 3-flu
• C ⁇ -C 6 alkyl for: C ⁇ -C 4 alkyl as mentioned above, and for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl f 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,
• C ⁇ -C ⁇ 5 alkyl for C ⁇ -C 6 alkyl for C ⁇ -C 6 alkyl as mentioned above, and for example n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl , 3-ethylpentyl, 4-ethylpentyl, 1, 1-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl, 1,4-dimethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl , 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1, 1-
• C ⁇ -C 6 -haloalkyl for: C-C ⁇ -alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / iodine, 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-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6- Fluoro-l-hexyl, 6-chloro-1-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6,6,6-trichloro-l-hexyl or dodecafluorohexyl, especially for chloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloro
• Hydroxy-C ⁇ -C 6 alkyl for: eg hydroxymethyl, 2-hydroxyeth-1-yl, 2-hydroxy-prop-l-yl, 3-hydroxy-prop-l-yl, 1-hydroxyprop-2-yl , 2-hydroxy-but-l-yl, 3-hydroxy-but-l-yl, 4-hydroxy-but-l-yl, l-hydroxy-but-2-yl, l-hydroxy-but-3-yl , 2-hydroxy-but-3-yl, l-hydroxy-2-methyl-prop-3-yl, 2-hydroxy-2-methyl-prop-3-yl or 2-hydroxymethyl-prop-2-yl, in particular for 2-hydroxyethyl;
• Cyano-C ⁇ -C 6 alkyl for: for example cyanomethyl, 1-cyanoeth-l-yl, 2-cyanoeth-l-yl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyano-prop -1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut-l -yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, l-cyanobut-3-yl, 2-cyano- but-3-yl, l-cyano-2-methyl-prop-3-yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl or 2- Cyanomethyl-prop-2-yl, especially for cyanomethyl or 2-cyanoethyl;
• Phenyl-CC 6 -alkyl for: e.g. benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-1-yl, 1-phenylbut-l -yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl , 4-phenylbut-2-yl, l- (phenylmethyl) -eth-1-yl, l- (phenylmethyl) -l- (methyl) -eth-l-yl or l- (phenylmethyl) prop-l -yl, especially for benzyl or 2-phenylethyl;
• Phenyl- (C ⁇ -C 6 -alkyl) carbonyloxy for: e.g. benzylcarbonyloxy, 1-phenylethylcarbonyloxy, 2-phenylethylcarbonyloxy, 1-phenylprop-1-ylcarbonyloxy, 2-phenylprop-l-ylcarbonyloxy, 3-phenylprop-1- ylcarbonyloxy, 1-phenylbut-l-ylcarbonyloxy, 2-phenylbut-1-ylcarbonyloxy, 3-phenylbut-ly.lcarbonyloxy, 4-phenylbut-1-ylcarbonyloxy, l-phenylbut-2-ylcarbonyloxy, 2-phenyl- but-2-ylcarbonyloxy, 3-phenylbut-2-ylcarbonyloxy, 4-phenyl-but-2-ylcarbonyloxy, 1- (phenylmethyl) -eth-1-ylcarbonyloxy, 1- (phenylmethyl) -1- (methyl
• Phenyl-C ⁇ -C 6 -alkylsulfonyloxy for: e.g. benzylsulfonyloxy, 1-phenylethylsulfonyloxy, 2-phenylethylsulfonyloxy, 1-phenylprop-1-ylsulfonyloxy, 2-phenylprop-l-ylsulfonyloxy, 3-phenylprop-1-ylsulfonyloxy, 1 -Phenylbut-l-ylsulfonyloxy, 2-phenylbut-1-ylsulfonyloxy, 3-phenylbut-l-ylsulfonyloxy, 4-phenylbut-1-ylsulfonyloxy, l-phenylbut-2-ylsulfonyloxy, 2-phenylbut-2 -ylsulfonyloxy, 3-phenylbut-2-ylsulfonyloxy, 4-phenyl
• (C ⁇ -C 6 -alkyl) carbonyl for: C0-CH 3 , CO-C 2 H 5 ,, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1, 1- Dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1, 1-dimethylpropylcarbonyl, 1, 2-dimethylpropylcarbonyl, 2, 2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentyl carbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1, 1-dimethylbutylcarbonyl, 1, 2-dimethylbutylcarbonyl, 1,
• (Ci-C ⁇ -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, e.g.
• (C ⁇ -C 6 -alkyl) carbonyloxy for: acetyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1, 1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy , 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1, 1-dimethylpropylcarbonyloxy,
• (C ⁇ -C 6 -haloalkyl) carbonyloxy for: a (C ⁇ -C 6 -alkyl) carbonyloxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetyloxy, dichloroacetyloxy , Trichloroacetyloxy, fluoroacetyloxy, difluoroacetyloxy, tri-fluoroacetyloxy, chlorofluoroacetyloxy, dichlorofluoroacetyloxy, chlorodifluoroacetyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2,2, 2-fluoro-carbonyloxy, 2,2, 2-fluoro-carbonyloxy, 2,2, 2-fluoro-2-carbonyloxy,
• (C ⁇ -C 6 alkyl) carbonylthio for acetylthio, ethylcarbonylthio, n-propylcarbonylthio, 1-methylethylcarbonylthio, n-butylcarbonylthio, 1-methylpropylcarbonylthio, 2-methylpropylcarbonylthio, 1, 1-dimethylethylcarbonylthio, n-pentyl- carbonyl 1-methylbutylcarbonylthio, 2-methylbutyl carbonylthio, 3-methylbutylcarbonylthio, 1, 1-dimethylpropylcarbonylthio, 1,2-dimethylpropylcarbonylthio, 2,2-dimethylpropylcarbonylthio, 1-ethylpropylcarbonylthio, n-hexylcarbonylthio, 1-methylpentylcarbonylthio, 2-methylpentylcarbonylthio Methylpentylcarbony
• - (Cx-C ⁇ -haloalkyl) carbonylthio for: a (C ⁇ -C 6 -alkyl) carbonylthio radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetylthio, dichloroacetylthio , Trichloroacetylthio, fluoroacetylthio, difluoroacetylthio, trifluoroacetylthio, chlorofluoroacetylthio, dichlorofluoroacetylthio, chlorodifluoroacetylthio, 2-fluoroethylcarbonylthio, 2-chloroethylcarbonylthio, 2-bromoethylcarbonylthio-carbonylthio-carbonylthio-carbonylthio-2-ethylcarbonylthio-carbonylthio-2-carbon
• - (C ⁇ -C 6 alkyl) carbamoyloxy for: methylcarbamoyloxy, ethylcarbamoyloxy, n-propylcarbamoyloxy, 1-methylethylcarbamoyloxy, n-butylcarbamoyloxy, 1-methylpropylcarbamoyloxy, 2-methylpropylcarbamoyloxy, 1, 1-dimethylethylcarbamoyloxy carbamoyloxy, 1-methylbutylcarbamoyloxy, 2-methylbutylcarbamoyloxy, 3-methylbutylcarbamoyloxy, 1, 1-dimethylpropylcarbamoyloxy, 1,2-dimethylpropylcarbamoyloxy, 2,2-dimethylpropylcarbamoyloxy, 1-ethylpropylcarbamoyloxycarbamoyloxy 1-MethylpentyIcarb
• (C ⁇ -C 6 -haloalkyl) carbamoyloxy for: a (C ⁇ -C 6 -alkyl) carbamoyloxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethylcarbamoyloxy , dichloro- methyIcarbamoyloxy, TrichlormethyIcarbamoyloxy, carbamoyloxy fluoromethyl, Difluormethylcarbamoyloxy, amoyloxy Trifluormethylcarb-, Chlorfluormethylcarbamoyloxy, Dichlorfluormethyl- carbamoyloxy, Chlordifluormethylcarbamoyloxy, 2-fluoroethyl carbamoyloxy, 2-Chlorethylcarbamoyloxy, 2-BromethyIcarbamoyloxy, 2-lodethylcarbamoyloxy, 2,
• C ⁇ -C 6 alkoxy for: e.g. 0CH 3 , OC 2 H 5 , 0CH 2 -C 2 H 5 , 0CH (CH 3 ) 2 , n-butoxy, OCH (CH 3 ) -C 2 H 5 , OCH 2 - CH (CH 3 ) 2 , OC (CH 3 ) 3 , n-pentoxy,
• C -C -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. Chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, tri luormethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2-difluoroethoxy -Trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-di-chloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoro
• Cx-C ß -haloalkoxy for: a C ⁇ -C 6 -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-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5,5, 5-trichloro-1-pentoxy, undecafluoropentoxy, 6 -Fluoro-l-hexoxy, 6-chloro-l-hexoxy, 6-bromo-l-hexoxy, 6-iodo-l-hexoxy, 6, 6, 6-trichloro-l-hexoxy or dodecafluorohexoxy, especially for chloromethoxy, fluoromethoxy , Difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-ch
• Hydroxy-C ⁇ -C 6 -alkoxy for: e.g. 0CH 2 -0H, OCH (CH 3 ) -OH, OCH 2 -CH 2 -OH, OCH (C 2 H 5 ) -OH, OCH 2 -CH (CH 3 ) -OH, 3-hydroxy-prop-1-yloxy, 1-hydroxybut-l-yloxy, 2-hydroxybut-l-yloxy, 3-hydroxybut-l-yloxy, 4-hydroxybut-l-yloxy, 1-hydroxy-but -2-yloxy, 2-hydroxybut-2-yloxy, 3-hydroxybut-2-yloxy, 4-hydroxybut-2-yloxy, l- (CH 2 -OH) -eth-l-yloxy, l- (CH 2 - OH) - l- (CH 3 ) -eth-l-yloxy or l- (CH 2 -OH) -prop-l-yloxy, in particular for OCH 2 -OH or OCH 2
• Cyano-C ⁇ -C 6 -alkoxy for: e.g. 0CH 2 -CN, 0CH (CH 3 ) -CN, OCH 2 -CH 2 -CN, 0CH (C 2 H 5 ) -0H, 0CH-CH (CH 3 ) - CN, 3-cyanoprop-l-yloxy, 1-cyanobut-l-yloxy, 2-cyanobut-l-yloxy, 3-cyanobut-l-yloxy, 4-cyanobut-l-yloxy, l-cyanobut- 2-yloxy, 2-cyanobut-2-yloxy, 3-cyanobut-2-yloxy, 4-cyanobut-2-yloxy, l- (CH 2 -CN) -eth- 1-yloxy, l- (CH 2 -CN) -l- (CH 3 ) -eth-l-yloxy or l- (CH 2 -CN) prop-1-yloxy, in particular for OCH 2 -
• Phenyl-Cx-C ⁇ -alkoxy for: e.g. Benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenylprop-l-yloxy, 2-phenylprop-l-yloxy, 3-phenylprop-l-yloxy, 1-phenylbut-l-yloxy, 2-phenylbut-l-yl- oxy, 3-phenylbut-l-yloxy, 4-phenylbut-l-yloxy, 1-phenylbut-2-yloxy, 2-phenylbut-2-yloxy, 3-phenylbut-2-yloxy, 4-phenylbut-2- yloxy, l- (benzyl) -eth-l-yloxy, l- (benzyl) -l- (methyl) -eth-l-yloxy or l- (benzyl) -prop-l-yloxy, especially for benzyloxy or 2- phenylethoxy;
• Heterocyclyl-Cx-C ß -alkoxy for: e.g. heterocyclylmethoxy, l- (heterocyclyl) ethoxy, 2- (heterocyclyl) ethoxy, l- (heterocyclicl) prop-l-yloxy, 2- (heterocyclyl) prop-l-yloxy , 3- (heterocyclic) prop-l-yloxy, l- (heterocyclyl) but-l-yloxy, 2- (heterocyclic) but-l-yloxy, 3- (heterocyclyl) but-l-yloxy, 4 - (Heterocyclic) but-l-yloxy, l- (heterocyclyl) but-2-yloxy, 2- (heterocyclic) but-2-yloxy, 3- (heterocyclyl) but-2-yloxy, 4- ( Heterocyclic) but-2-yloxy, l- (
• Phenyl-Cx-C ⁇ -alkylthio for: e.g. Benzylthio, 1-phenylethylthio, 2-phenylethylthio, 1-phenylprop-l-ylthio, 2-phenylprop-l-ylthio, 3-phenylprop-l-ylthio, 1-phenylbut-l-ylthio, 2-phenylbut- l-ylthio, 3-phenylbut-l-ylthio, 4-phenylbut-l-ylthio, l-phenylbut-2-ylthio, 2-phenylbut-2-ylthio, 3-phenylbut-2-ylthio, 4-phenylbut- 2-ylthio, l- (phenylmethyl) -eth-1-ylthio, l- (phenylmethyl) -l- (methyl) -eth-l-ylthio or l- (phenylmethyl) prop-l-
• SCH 3 - C -C 6 alkylthio for: SCH 3 , SC 2 H 5 , SCH 2 -C 2 H 5 , SCH (CH 3 ) 2 , n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC (CH 3 ) 3 , n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methyl butylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio,
• C ⁇ -C 6 -haloalkylthio for: Cx-C ⁇ -alkylthio as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for SCHF 2 , SCF 3 , chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethyl - Thio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2, 2, 2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chlorine -2,2-di-fluoroethylthio, 2,2-dichloro-2-fluoroethylthio, SC 2 F 5 , 2-fluoropropylthio, 3-flu
• C ⁇ -C 6 -alkylsulfinyl for: SO-CH 3 , SO-C 2 H 5 , n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, n- Pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1-hexylsulfyl, 1-hexylsulfyl, 1-hexylsulfyl,
• 4-methylpentylsulfinyl 1, 1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3, 3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl Ethylbutylsulfinyl, 1, 1, 2-trimethylpropylsulfinyl, 1,2, 2-trimethylpropylsulfinyl, 1-ethyl-l-methylpropylsulfinyl or l-ethyl-2-methylpropylsulfinyl, in particular for SO-CH 3 ;
• Ci-Cg-alkylsulfonyl for: S0 2 -CH 3 , S0 2 -C 2 H 5 , n-propylsulfonyl, S0 2 -CH (CH 3 ) 2 , n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, S ⁇ 2 - C (CH 3 ) 3 , n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2, 2-dimethylpropylsulfonyl, 1-ethyl-propylsulfonyl , 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methyl
• C ⁇ -C 6 alkylsulfonyloxy for: 0-S0 2 -CH 3 , 0-S0 2 -C 2 H 5 , n-propylsulfonyloxy, 0-S0 2 -CH (CH 3 ) 2 , n-butylsulfonyloxy, 1 -Methyl-propylsulfonyloxy, 2-methylpropylsulfonyloxy, 0-S0 2 -C (CH 3 ) 3 , n-pentylsulfonyloxy, 1-methylbutylsulfonyloxy, 2-methylbutylsulfonyloxy, 3-methylbutylsulfonyloxy, 1, 1-dimethylpropylsulfonyloxy, 1 -Dimethylpropylsulfonyloxy, 2,2-dimethylpropylsulfonyloxy, 1-ethylpropylsulfonyloxy, n
• C ⁇ -C 6 -haloalkylsulfonyloxy for: Cx-C ⁇ -alkylsulfonyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CICH 2 -SO 2 -O-, CH (Cl) 2 -S0 2 -0-, C (Cl) 3 -S0 2 -0-, FCH 2 -S0 2 -0-,
• (C ⁇ -C 6 -alkyl) aminocarbonyl for: (C ⁇ -C 4 -alkyl) aminocarbonyl as mentioned above and, for example, n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethyopropylaminocarbonyl, 2-dimethyl , n-Hexylaminocarbonyl, 1,1-Dimethylpropylaminocarbonyl, 1, 2-Dimethylpropylaminocarbonyl, 1-Methylpentylaminocarbonony1, 2-Methylpentylaminocarbonyl, 3-Methylpentylaminocarbonyl, 4-Methylpentylaminocarbonyl, 1, 1-Dimethylbutylaminocarbonyl, 1,2-Dimethylbutyl , 3-dimethylbutylaminocarbonyl, 2,2-dimethyl
• Di (C ⁇ -C 6 -alkyl) aminocarbonyl for: e.g. N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-dipropylaminocarbonyl, N, N-di- (1-methylethyl) aminocarbonyl, N, N-dibutylaminocarbo- nyl, N, N-Di- (1-methylpropy1) aminocarbonyl, N, N-Di- (2-methylpropyl) aminocarbonyl, N, N-Di- (1, 1-dimethylethyl) aminocarbonyl, N-ethyl- N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N- (1-methylethyl) aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N- (1-methylpropylaminocarbonyl, N-
• (-C-C 6 alkyl) iminooxycarbonyl for: methyliminooxycarbonyl, ethyliminooxycarbonyl, n-propyliminooxycarbonyl, 1-methyl-ethyliminooxycarbonyl, n-butyliminooxycarbonyl, 1-methyl-propyliminooxycarbonyl, 2-methylpropyliminooxycarbonyl, 1, 1-dimethyloxyinoylyl -Methylbutyliminooxycarbonyl, 2-Methylbutyliminooxycarbonyl, 3-Methylbutyliminooxycarbonyl, 1, 1-Dimethylpropyliminooxycarbonyl, 1,2-Dimethylpropyliminooxycarbonyl, 2, 2-Dimethylpropyliminooxycarbonyl, 1-Ethylpropyliminooxycarbonyl, n-Hexyliminooxycarbonyl, 1-Methylpentyliminooxycarbonyl, 2-
• C ⁇ -C 6 alkylidene aminoxy for: 1-propylidene aminoxy, 2-propylidene aminoxy, 1-butylidene aminoxy, 2-butylidene aminoxy or 2-hexylidene aminoxy, especially for butylidene aminoxy or 2-propylidene aminoxy;
• C ⁇ -C 6 -alkyliminooxy for: methyliminooxy, ethyliminooxy, n-propyliminooxy, 1-methylethyliminooxy, n-butyliminooxy, 1-methylpropyliminooxy, 2-methylpropyliminooxy, n-pentyliminooxy, n-hexyliminooxy, 1-methylpentyliminooxy, 2-methylpentyliminooxy pentyliminooxy, 3-methylpentyliminooxy or 4-methylpentyl iminooxy, especially for methyliminooxy, ethyliminooxy or 1-methylethyliminooxy;
• C ⁇ -C 6 -alkoxyamino-C ⁇ -C 6 -alkyl for: e.g. CH 2 -NH-OCH 3 , CH 2 -NH-OC 2 H 5 , CH 2 -NH-OCH 2 -C 2 H 5 , CH 2 - NH-OCH (CH 3 ) 2 , CH 2 -NH-OCH 2 -CH 2 -C 2 H 5 , CH 2 -NH-OCH (CH 3 ) -C 2 H 5 ,
• C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkylamino-C ⁇ -C 6 -alkyl for: C ⁇ -C ⁇ -alkylamino-C ⁇ -C 6 -alkyl such as CH 2 -NH-CH 3 , CH 2 -NH- C 2 H 5 , CH 2 -NH-CH 2 -C 2 H 5 , CH 2 -NH-CH (CH 3 ) 2 , CH 2 -NH- (CH 2 ) 3 -CH 3 , CH 2 -NH-CH (CH 3 ) -C 2 H 5 , CH 2 -NH-CH 2 -CH (CH 3 ) 2 , CH 2 -NH-C (CH 3 ) 3 , CH 2 -NH- (CH 2 ) 4-CH 3 , (1-Methylbutylamino) methyl, (2-methylbutylamino) methyl, (3-methylbutylamino) methyl, (2, 2-dimethylpropylamino) methyl
• C ⁇ -C 6 -alkyloximino-C ⁇ -C 6 -alkyl for: by C ⁇ -C 6 -alkyloximino such as methoxyimino, ethoxyimino, 1-propoxyimino, 2-propoxy-imino, 1-methylethoxyimino, n-butoxyimino, sec.-butoxyimino, tert-Butoxyimino, 1-methyl-1-propoxyimino, 2-methyl-l-prop-oxyimino, l-methyl-2-propoxyimino, 2-methyl-2-propoxyimino, n-pentoxyimino, 2-pentoxyimino, 3-pentoxyimino , 4-pentoxyimino, 1-methyl-l-butoxyimino, 2-methyl-l-butoxyimino, 3-methyl-l-butoxyimino, l-methyl-2-butoxyimino, 2-methyl-2-butoxyimino, 3-methyl -2-butoxyimino,
• C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkyl for: C ⁇ -C 6 -alkoxy - as mentioned above - substituted C ⁇ -C 6 -alkyl, for example for CH 2 -OCH 3 , CH 2 -OC 2 H 5 , n-propoxymethyl, CH 2 -OCH (CH 3 ) 2 , n-butoxymethyl, (1-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, 1-dimethylethoxy) ethyl, 2- (methoxy) propy1, 2- (
• Di (C ⁇ -C 6 -alkoxy) -C ⁇ -C 6 -alkyl for: for example 2,2-dimethoxyethyl or 2,2-diethoxyethyl;
• CC 6 -alkoxy-C ⁇ -C 6 -alkoxy for: Cx-C ⁇ -alkoxy substituted by Cx-C ⁇ -alkoxy as mentioned above, for example for OCH 2 -OCH 3 , OCH 2 -OC 2 H 5 , n-propoxymethoxy, OCH 2 -OCH (CH 3 ) 2 , n-butoxymethoxy, (1-methylpropoxy) methoxy, (2-methylpropoxy) methoxy, OCH -OC (CH 3 ) 3 , 2- (methoxy) ethoxy, 2- (ethoxy ) ethoxy, 2- (n-propoxy) ethoxy, 2- (l-methylethoxy) ethoxy, 2- (n-butoxy) ethoxy, 2- (1-methylpropoxy) ethoxy, 2- (2-methylpropoxy) ethoxy, 2- (1, 1-dimethylethoxy) ethoxy,
• (C ⁇ -C 6 -alkoxy) carbonyl-C ⁇ -C 6 -alkoxy for: Cx-Cg-alkoxy substituted by (C ⁇ -C 6 -alkoxy) carbonyl as mentioned above, for example for 0CH 2 -C0-0CH 3 , 0CH 2 -C0-0C 2 H 5 , 0CH 2 -C0-0CH 2 -C 2 H 5 , OCH 2 -CO-OCH (CH 3 ), n-butoxycarbonyl-methoxy, l- (methoxycarbonyl) ethoxy, 2 - (Methoxycarbonyl) ethoxy, 2- (ethoxycarbonyl) ethoxy, 2- (n-propoxycarbonyl) ethoxy, 2- (n-butoxycarbonyl) ethoxy, 3- (methoxycarbonyl) propoxy, 3- (ethoxycarbonyl) propoxy , 3- (n-propoxycarbonyl) propoxy, 3- (n-butoxycarbon
• (C ⁇ -C 6 -alkoxy) carbonyl-C ⁇ -C 6 -alkyl for: Cx-C ß- alkyl substituted by (CC ß -alkoxy) carbonyl as mentioned above, e.g. for methoxycarbonylmethyl, ethoxycarbonylmethyl, 1- (methoxycarbonyl) ethyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 3- (methoxycarbonyl) propyl, 4- (meth- oxycarbonyl) butyl, 5- (methoxycarbonylpentyl or 6- (methoxycarbonyl) hexyl;
• C ⁇ -C 6 -alkylthio-C ⁇ -C 6 -alkoxy of: by C ⁇ -C 6 -alkylthio as mentioned above substituted C ⁇ -C6 alkoxy, eg for OCH 2 SCH 3, OCH 2 -S-C 2 H 5, OCH 2 -SCH 2 -C2H 5 , OCH 2 -SCH (CH 3 ) 2 , n-butylthiomethoxy, OCH 2 -SCH (CH 3 ) -C 2 H 5 , OCH 2 -SCH 2 -CH (CH 3 ) 2 , 0CH 2 -SC (CH 3 ) 3 , 2- (SCH 3 ) ethoxy, 2- (SC 2 H 5 ) ethoxy, 2- (SCH 2 -C 2 H 5 ) - ethoxy, 2- [SCH (CH 3 ) 2 ] ethoxy, 2- (n-butylthio) ethoxy,
• C 3 -C 6 alkenyl for: for example prop-2-en-l-yl, n-buten-4-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop-2- en-l-yl, 2-butene
• C 3 -Cg haloalkenyl for: C 3 -C 6 alkenyl as mentioned above, partially or completely by fluorine, chlorine and / or
• Bromine is substituted, e.g. 2-chloroallyl, 3-chloroallyl, 2,3-dichlorallyl, 3,3-dichlorallyl, 2,3,3-trichlorallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3- Dibromallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl, in particular for 2-chloroallyl or 3,3-dichloroallyl;
• C 2 -C 6 alkenyl for: ethenyl or one of the radicals mentioned under C 3 -C 6 alkenyl, in particular for ethenyl or prop-2-en-1-yl;
• C 3 -C 6 alkenyloxy for: prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n -Butene-3-yloxy, 1-methyl-prop-1-en-1-yloxy, 2-methyl-prop-1-en-1-yloxy, 1-methyl-prop-2-en-1-yloxy, 2 -Methyl-prop-2-en-l-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methyl-but -l-en-l-yl-oxy, 2-methyl-but-l-en-l-yloxy, 3-methyl-but-l-en-l-yloxy, l-methyl-but-2-en-l -yloxy, 2-methyl-but-2-en-l
• C 2 -C 6 alkynyloxy for: ethynyloxy or one of the radicals mentioned under C 3 -Ce-alkynyloxy, in particular for ethynyloxy or prop-2-yn-l-yloxy;
• Phenyl-C 3 -C 6 -alkynyloxy for: e.g. 3-phenylprop-2-in-l-yloxy, 4-phenylbut-2-in-l-yloxy, 3-phenylbut-3-in-2-yloxy, 5- Phenylpent-3-in-1-yloxy or 6-phenylhex-4-in-1-yloxy, especially for 3-phenylprop-2-in-1-yloxy or 3-phenylbut-3-in-2-yloxy;
• Heterocyclyl-C 3 -C 6 -alkynyloxy for: for example 3- (heterocyclyl) prop-2-in-l-yloxy, 4- (heterocyclyl) but-2-in-l-yloxy, 3- (heterocyclic) but -3-in-2-yloxy, 5- (heterocyclyl) pent-3-in-1-yloxy or 6- (heterocyclyl) hex-4-in-l-yloxy, especially for 3- (heterocyclyl) prop-2- in-l-yloxy or 3- (heterocyclyl) but-3-in-2-yloxy;
• C 3 -C 6 alkynylthio for: prop-1-in-l-ylthio, prop-2-in-l-ylthio, n-but-1-in-l-ylthio, n-but-l-in-3 -ylthio, n-but-1-in-4-ylthio, n-but-2-in-1-ylthio, n-pent-1-in-1-ylthio, n-pent-1-in-3-ylthio , n-pent-1-in-4-ylthio, n-pent-1-in-5-ylthio, n-pent-2-in-1-ylthio, n-pent-2-in-4-ylthio, n Pent-2-in-5-ylthio, 3-methyl-but-l-in-3-ylthio, 3-methylbut-l-in-4-ylthio, n-hex-1-in-l-ylthio, n -Hex
• C 2 -C 6 alkynylthio for: ethynylthio or one of the radicals mentioned under C 3 -C 6 -alkynylthio, in particular for ethynylthio or prop-2-ylthio;
• (C 3 -C 6 alkenyloxy) carbonyl for: prop-1-en-l-yloxycarbonyl, prop-2-en-l-yloxycarbonyl, 1-methylethenyloxycarbonyl, n-buten-1-yloxycarbonyl, n-buten-2- yloxycarbonyl, n-butene-3-yloxycarbonyl, 1-methyl-prop-l-en-l-yloxycarbonyl, 2-methyl-prop-1-en-l-yloxycarbonyl, l-methyl-prop-2-en-l- yloxy carbonyl, 2-methyl-prop-2-en-l-yloxycarbonyl, n-penten-1-yloxycarbonyl, n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl, n-penten-4-yloxycarbonyl, 1- Methyl-but-l-en-l-yloxycarbonyl, 2-methyl-
• (C 3 -C 6 alkenyloxy) carbonyl -CC 6 alkyl for: by (C 3 -C 6 alkenyloxy) carbonyl as mentioned above, preferably prop-2-en-1-yl-oxycarbonyl, substituted C ⁇ -C 6 alkyl, for example prop-2-en-1-yl-oxycarbonyl-methyl;
• (C -C 6 alkenyl) carbonyloxy for: ethenylcarbonyloxy, prop-1-en-l-ylcarbonyloxy, prop-2-en-l-ylcarbonyloxy, 1-methyl-ethenylcarbonyloxy, n-buten-1-ylcarbonyloxy, n-butene -2-yl-carbonyloxy, n-buten-3-ylcarbonyloxy, 1-methyl-prop-l-en-1-ylcarbonyloxy, 2-methyl-prop-l-en-l-ylcarbonyloxy, l-methyl-prop-2 -en-l
• (C 2 -C 6 alkenyl) carbonylthio for: ethenylcarbonylthio, prop-1-en-l-ylcarbonylthio, prop-2-en-l-ylcarbonylthio, 1-methylethenylcarbonylthio, n-buten-1-ylcarbonylthio, n- Buten-2-yl-carbonylthio, n-buten-3-ylcarbonylthio, 1-methyl-prop-l-en-1-ylcarbonylthio, 2-methyl-prop-l-en-l-ylcarbonylthio, l-methyl-prop- 2-en-1-ylcarbonylthio, 2-methyl-prop-2-en-1-ylcarbonylthio, n-penten-1-ylcarbonylthio, n-penten-2-ylcarbonylthio, n-penten-3-ylcarbonylthio, n-penten-4-yl-carbonylthio,
• (C 2 -C 6 alkynyl) carbonyloxy for: ethynylcarbonyloxy, prop-1-in-1-ylcarbonyloxy, prop-2-in-1-ylcarbonyloxy, n-but-1-in-1-ylcarbonyloxy, n-but- l-in-3-ylcarbonyloxy, n-but-l-in-4-ylcarbonyloxy, n-but-2-in-l-ylcarbonyloxy, n-pent-1-in-l-ylcarbonyloxy, n-pent-l- in-3-ylcarbonyloxy, n-pent-l-in-4-ylcarbonyloxy, n-pent-l-in-5-ylcarbonyloxy, n-pent-2-in-l-ylcarbonyloxy, n-pent-2-in-ylcarbonyloxy, n-pent-2-in-ylcarbonyloxy, n-pent-2-
• C 3 -C 6 alkynylsulfonyloxy for: prop-1-in-1-ylsulfonyloxy, prop-2-in-1-ylsulfonyloxy, n-but-1-in-1-ylsulfonyloxy, n-but-1-in-3 -ylsulfonyloxy, n-but-1-in-4-ylsulfonyloxy, n-but-2-in-1-ylsulfonyloxy, n-pent-1-in-1-ylsulfonyloxy, n-pent-1-in-3-ylsulfonyloxy , n-Pent-1-in-4-ylsulfonyloxy, n-Pent-1-in-5-ylsulfonyloxy, n-Pent-2-in-1-ylsulfonyloxy, n-Pent-2-in-4-ylsulfonyloxy, n Pent
• Ci-C ⁇ -alkoxy-Cs-Cg-alkenyloxy for: C 3 -C 6 -alkenoxy substituted by Ci-C ⁇ -alkoxy as mentioned above, for example for methylprop-2-en-l-yloxy;
• C 3 -C 6 alkenyloxy -CC 6 alkyl for: by C 3 -C 6 alkenyloxy as mentioned above, preferably allyloxy, 2-methyl-prop-2-en-l-yloxy, but-l-ene -3-yloxy, but-l-en-4-yloxy or but-2-en-1-yloxy-substituted Ci-C ⁇ -alkyl, e.g. for allyloxymethyl, 2-allyloxyethyl or but-l-en-4- yloxymethyl;
• C 3 -C 6 alkynyloxy -CC 6 alkyl for: by C 3 -C 6 -alkynyloxy as mentioned above, preferably propargyloxy, but-l-in-3-yl-oxy, but-l-in-4 -yloxy or But-2-in-l-yloxy, substituted Ci-C ⁇ -alkyl, for example for propargyloxymethyl or 2-propargyloxyethyl;
• C 3 -C 6 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
• C 3 -C 6 cycloalkyloxy for: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy;
• C 3 -C 6 cycloalkylthio for: cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio;
• C 3 -C 6 cycloalkylcarbonyloxy for: cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or cyclohexylcarbonyloxy;
• C 3 -C 6 cycloalkylsulfonyloxy for: cyclopropylsulfonyloxy, cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or cyclohexylsulfonyloxy;
• Cycloalkenyloxy for: cyclopent-1-enyloxy, cyclopent-2-enyloxy, cyclopent-3-enyloxy, cyclohex-1-enyloxy, cyclohex-2-enyloxy, cyclohex-3-enyloxy, cyclohept-1 -enyloxy, cyclohept-2-enyloxy, cyclohept-3-enyloxy or cyclohept-4-enyloxy.
• 3- to 7-membered azaheterocycles which in addition to carbon ring members may also contain an oxygen or sulfur atom as a ring member, are e.g.
• 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, l, 3-dioxolan-2-yl, l,
• 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 5-0xazolyl, 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, 1,2,4-oxadiazol-5-yl and 1,3,4
• the variables preferably have the following meanings, individually or in combination:
• R A CO 2 R 1 , halogen, cyano, OR 2 or -CC 3 alkyl;
• X, Y and Y ' are independently 0 or S;
• T is a chemical bond or 0;
• U is a chemical bond, -CC alkylene, 0 or S;
• R hydrogen, C (0) ORi °, C (0) SR 10 , C (S) 0R 10 , C (S) SR 10 , CHO, CN, C (0) R 2 , C (0) NR n R 12 , C (S) NR U R 12 , C (0) NHC (0) OR 12 ', C (0) NHS (0) 2 R 12 ', C (0) NHS (0) 2 OR 12 '; R 1 is hydrogen or -CC 3 alkyl;
• R 2 C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C ⁇ -C 3 haloalkyl, Cx-Cs-alkoxycarbonyl-Cx -Cs-alkyl, cyano -CC 3 -alkyl, benzyl, which can be substituted with halogen, C 1 -C 4 -alkyl or trifluoromethyl, or
• Phenyl which can be substituted with halogen, -CC 4 -alkyl, trifluoromethyl or -CC 4 -alkoxy;
• R 3 is hydrogen, fluorine or chlorine
• R 4 is chlorine, trifluoromethyl or cyano
• R 5 is hydrogen, hydroxy, mercapto, cyano, nitro, halogen, C ⁇ -C 6 -alkyl, C 6 haloalkyl, Ci-C ⁇ -haloalkoxy, C ⁇ -C6 haloalkylthio, C ⁇ -C 6 alkoxy (C ⁇ -C 6 -alkyl) carbonyl, -C-C 6 -alkylthio- (-C-C 6 -alkyl) carbonyl, (Ci-C ⁇ -alkyl) -iminooxycarbonyl, C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkyl , C ⁇ -C 6 -alkoxyamino-Cx-Cg-alkyl, C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkylamino-no-Ci-C ⁇ -alkyl,
• Halogen nitro, cyano, hydroxy, C 3 -C 6 -Cycloalky, C ⁇ -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 alkenyloxy,
• R 6 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 7 cycloalkyl, or 3- to 7-membered saturated Heterocyclyl containing one or more oxygen and / or sulfur atoms;
• R 7 is hydrogen or C ⁇ -C 6 alkyl
• R 8 is hydrogen or C ⁇ -C 3 alkyl
• R 9 is hydrogen, C ⁇ -C 3 alkyl
• R 10 C ⁇ -C 15 alkyl, C 3 -C 8 cycloalkyl, C 2 -C ⁇ 0 alkenyl, C 3 -C 10 alkynyl, C ⁇ -C 6 haloalkyl, C ⁇ -C 6 alkoxy-C ⁇ -C 6 alkyl,
• Phenyl or benzyl which are each one to five times by halogen, C effet-C 4 -alkyl, C ⁇ -C -haloalkyl, C ⁇ -C 4 -alkoxy, C ⁇ -C 4 -haloalkoxy, amino, C 2 -C 4 - Monoalkylamino, C ⁇ -C 4 -dialkylamino, C ⁇ -C 4 -alkoxycarbonyl, nitro or cyano may be substituted;
• R 11 is hydrogen, C ⁇ -C 6 alkyl or C ⁇ -C 6 alkoxy
• R 12 is hydrogen, C ⁇ -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C ⁇ -C 6 haloalkyl, C ⁇ -Ce alkoxy-C ⁇ -C 6 alkyl, phenyl or benzyl which are substituted one to five times by halogen, C ⁇ -C 4 -alkyl, C ⁇ -C 4 -haloalkyl, C ⁇ -C 4 -alkoxy, C ⁇ -C 4 -dialkylamino, C ⁇ -C 4 -alkoxycarbonyl, nitro or cyano could be; or
• R 11 and R 12 together with the common nitrogen atom represent a saturated or unsaturated 4- to 7-membered azaheterocycle
• R 12 has the meanings given for R 12 , with the exception of hydrogen;
• R 13 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C ⁇ -C 6 alko - xy-C ⁇ -C 6 -alkyl, cyano-C ⁇ -C 6 -alkyl, (C ⁇ -C 6 -alkoxy) carbonyl- C ⁇ -C 6 -alkyl or phenylalkyl, the phenyl ring being mono- to triple by halogen, cyano, Nitro, C ⁇ -C 3 alkyl, C ⁇ -C 3 haloalkyl or C ⁇ -C 3 alkoxy may be substituted;
• R 14 is hydrogen, C ⁇ -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C ⁇ -C 6 alkoxy-C ⁇ -C 6 alkyl, ( C ⁇ -C 6 -alkoxy) carbonyl-C ⁇ -C 6 -alkyl, C 3 -C 6 -alkenyloxycarbonyl- C ⁇ -C 6 -alkyl,
• Phenyl or benzyl which may be unsubstituted on the phenyl ring or substituted one to three times by halogen, cyano, nitro, C ⁇ -C 3 alkyl, C ⁇ -C 3 haloalkyl or C ⁇ -C 3 alkoxy;
• R 14 has the meanings given for R 14 , except hydrogen
• R 15 is hydrogen, hydroxy, C ⁇ -C 6 alkyl, C ⁇ -C 6 alkoxy,
• R 16 is hydrogen, halogen, C ⁇ -C 6 -alkyl, C ⁇ -C 6 -haloalkyl,
• R 17 is hydrogen, cyano, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Cx-Ce-alkoxy-C -C ⁇ -alkyl or (C ⁇ -C 6 alkoxy) carbonyl;
• R 18 is hydrogen, C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C ⁇ -C 6 haloalkyl, C ⁇ -C 6 alkoxy -C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxy, (C ⁇ -C 6 -alkoxy) carbonyl- C ⁇ -C 6 -alkyl,
• Phenyl or phenyl- (Cx-C ß- alkyl), the latter two phenyl radicals being substituted by halogen, cyano, nitro, C ⁇ -C 3 -alkyl, C ⁇ -C 3 -haloalkyl, C ⁇ -C 3 -alkoxy or (C ⁇ -C 3 -alkoxy) carbonyl may be substituted;
• R 19 , R 20 independently of one another C ⁇ -Ce-alkyl, C ⁇ -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C ⁇ -C 6 -alkoxy-C ⁇ -C 6 - alkyl, or
• R 21 is hydrogen, cyano, halogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl or C ⁇ -C 6 alkoxy;
• R 22 is hydrogen, OR 31 , SR 31 , C ⁇ -C 6 alkyl, which can also carry one or two C ⁇ -C 6 alkoxy substituents, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C ⁇ -C 6 -haloalkyl or C 3 -C 6 cycloalkyl;
• R 23 is hydrogen, cyano, halogen, C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;
• R 24 is hydrogen, cyano, halogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 alkoxy or C ⁇ -C 6 haloalkyl
• R2 5 is hydrogen, cyano or Ci-C ß alkyl
• R 26 , R 31 independently of one another are hydrogen, C ⁇ -C 6 -alkyl
• C ⁇ -C 6 haloalkyl C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, where the latter 4 groups can each carry one or two of the following radicals: cyano, halogen, Cx-C ß -alkoxy, C ⁇ -C 6 alkylcarbonyl, (C ⁇ -C 6 alkoxy) carbonyl; or (C ⁇ -C 6 -alkyl) carbonyl, (C ⁇ -C 6 -alkoxy) carbonyl, phenyl or phenyl-Cx-C ß- alkyl;
• R 27 , R 28 , R 29 , R 30 independently of one another hydrogen, C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C ⁇ - C 6 -haloalkyl, C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkylcarbonyl, (Cx-C ß -alkoxy) carbonyl, or
• R 27 and R 28 and / or R 29 and R 30 together with the respective common nitrogen atom for a saturated or unsaturated 4- to 7-membered azaheterocycle which, if desired, can contain an oxygen atom or an —NH group in addition to carbon ring members;
• R 4 stands in particular for halogen, and especially for fluorine or chlorine.
• R A stands in particular for hydrogen, ie m stands for 0.
• R 5 in Ql stands for:
• each of the 3 last-mentioned radicals may if desired, carry one to three substituents each selected from the group consisting of halogen, C ⁇ -C 6 alkoxy,
• R 13 is C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C ⁇ -C 6 cyanoalkyl and C ⁇ -C 6 alkoxy-carbonyl-C ⁇ -C 6 alkyl;
• R 16 is hydrogen, C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxy, C ⁇ -C 6 -alkoxycarbonyl-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxycarbonyl-C ⁇ -C 6 -alkoxy and phenoxycarbonyl- C ⁇ -C 6 alkoxy;
• R 17 is hydrogen, -CC 6 alkyl
• R 19 and R 20 are independently C ⁇ -C 6 alkyl
• R 21 is hydrogen, halogen, C ⁇ -C 6 alkyl
• R 22 is hydroxy, C ⁇ -C 6 alkoxy, C ⁇ -C 6 alkylthio, C ⁇ -C 6 alkoxycarbonyl-C ⁇ -C ⁇ -alkyl;
• R 26 C ⁇ -C 6 alkyl, C 3 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C ⁇ -C 6 alkoxycarbonyl-C ⁇ -C 6 alkyl, C 3 -C 6 alkenyloxycarbonyl-Cx-C ß- alkyl, C 3 -C 6 -alkynyloxycarbonyl-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxyalkyl;
• R 27 is hydrogen, C ⁇ -C 6 alkyl
• R 28 is hydrogen, Ci-C ⁇ -alkyl, -CC 6 alkoxy,
• Azaheterocycle which may have one or two non-adjacent oxygen atoms in the ring.
• R is preferably not hydrogen, in particular when Q is one of the radicals Q1, Q4, Q5 or Q6 and when Z is oxygen.
• R 2 C -C 6 alkyl
• R 11 is hydrogen or C -C 6 alkyl
• R 12 is hydrogen, C ⁇ -C 6 alkyl or C ⁇ -C 6 alkoxy
• R particularly preferably stands for:
• a special class relates to compounds of the general formulas Ia and Ib, in which Q is Ql.
• the variables have the meanings mentioned above, and particularly preferably the following meanings:
• R 11 is hydrogen or C ⁇ -C 6 alkyl
• R 12 is hydrogen, C ⁇ -C 6 alkyl or C ⁇ -C 6 alkoxy
• R 3 is hydrogen or halogen, in particular fluorine or chlorine
• R 4 is hydrogen, halogen, in particular fluorine or chlorine or cyano, and
• R 5 C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 haloalkenyl, C ⁇ -C 6 alkoxy, C ⁇ -C 6 haloalkoxy, C ⁇ - C 6 alkylthio, C ⁇ -C 6 haloalkylthio, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C ⁇ -C 6 haloalkenyloxy, C 3 -C 6 alkenylthio, C 3 -C 6 -Halogenalkenylthio, C ⁇ -C 6 -alkoxycarbonyl-C ⁇ -C 6 -alkoxy, C 3 -C 6 -alkenyloxycarbonyl-C ⁇ -C 6 -alkoxy, C 3 -C ⁇ -alkynyloxycarbonyl-C ⁇ -C 6 -alkoxy, [C ⁇ -C 6 -al
• R 13 C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C ⁇ -C 6 cyanoalkyl and C ⁇ -C 6 alkoxy-carbonyl-Cx-C ⁇ -alkyl;
• R 16 is hydrogen, C ⁇ -C 6- alkyl, C ⁇ -C 6 -alkoxy, C ⁇ -C 6 -alkoxycarbonyl-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxycarbonyl-C ⁇ -C 6 -alkoxy and
• R 17 is hydrogen, C ⁇ -C 6 alkyl
• R 21 is hydrogen, halogen, C ⁇ -C 6 alkyl
• R 22 is hydroxy, C ⁇ -C 6 alkoxy, C ⁇ -C 6 alkylthio, C ⁇ -C 6 alkoxycarbonyl-C ⁇ -C 6 alkyl; R 26 C ⁇ -C 6 alkyl, C 3 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C ⁇ -C 6 alkoxycarbonyl-C ⁇ -C 6 alkyl, C 3 -C 6 -alkenoxycarbonyl-C ⁇ -C 6 -alkyl, C 3 -C 6 -alkynyloxycarbonyl-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxyalkyl;
• R 27 is hydrogen, C ⁇ -C 6 alkyl
• R 28 is hydrogen, C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxy,
• Azaheterocycle which may have one or two non-adjacent oxygen atoms in the ring.
• R 5 has the following meaning:
• R 5 COOH, C ⁇ -C 4 -alkoxyiminomethyl, C ⁇ -C 4 -alkoxy, C 3 -C 6 -CV-cloalkyloxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -alkenyloxyiminomethyl, (C ⁇ -C -alkoxycarbonyl) -C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxyiminomethyl, 2- [C ⁇ -C 4 -alkoxycarbonyl] -2-chloroethyl, 2nd - [C ⁇ -C 4 -alkoxycarbonyl] -2-chlorethenyl, C ⁇ -C 4 -alkoxycarbonyl, (C ⁇ -C 6 -alkoxycarbonyl) - C ⁇ -C 4 -alkoxy, (C ⁇ -C 6 -alkoxycarbon
• R 17 is C ⁇ -C 4 alkoxy and R 18 C ⁇ -C 4 alkoxy or C ⁇ -C 4 alkoxycarbonyl-C ⁇ -C 4 alkoxy.
• R 1 , R 2 , R 11 , R 12 and R 12 have the following meanings: R 1 C ⁇ -C 6 alkyl,
• R 11 is hydrogen or -CC 6 alkyl
• R 12 is hydrogen, C ⁇ -C 6 alkyl or C ⁇ -C 6 alkoxy
• R 12 is C -C 6 alkyl and C -C 6 alkyloxy
• R 3 is hydrogen or halogen
• R 4 is hydrogen or halogen
• U is a single bond, oxygen or C ⁇ -C 4 alkylene
• R 6 is hydrogen, halogen, cyano, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C cycloalkyl, saturated C 3 -C 7 heterocyclyl, the one or two heteroatoms selected from oxygen and sulfur in the ring has, Cx-C ß -alkoxyalkyl, cyano-C ⁇ -C 6 -alkyl, C0 2 H, C ⁇ -C 6 -alkoxycarbonyl and C ⁇ -C 6 -alkoxycarbonyl-C ⁇ -C 6 -alkyl, C 3 -C 6 Alkenyl or C 3 -C 6 alkynyl.
• R 1 C ⁇ -C 6 alkyl
• R 2 C ⁇ -C 6 alkyl
• R 11 is hydrogen or C ⁇ -C 6 alkyl
• R 12 is hydrogen, C ⁇ -C 6 alkyl or C ⁇ -C 6 alkoxy
• R 3 is hydrogen or halogen
• T is a single bond, oxygen or C ⁇ -C 4 alkylene
• R 7 is hydrogen, halogen, cyano, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 3 -C 7 cycloalkyl, saturated C 3 -C 7 heterocyclyl, the one or two heteroatoms selected from oxygen and
• Another class relates to compounds of the general formulas Ia and Ib, in which Q is Q6.
• the variables have the aforementioned meanings and, independently of one another, have the following meanings:
• R 2 C ⁇ -C 6 alkyl, R 11 is hydrogen or C ⁇ -C 6 alkyl
• R 12 is hydrogen, C ⁇ -C 6 alkyl or Cx-Cg alkoxy
• R 3 is hydrogen or halogen
• R 4 is hydrogen or halogen
• R 8 and R 9 are independently hydrogen, C ⁇ -C 6 alkyl, halogen, cycloalkyl or C ⁇ -C 6 haloalkyl, or
• R 8 and R 9 together with the carbon atom to which they are attached mean a carbonyl group.
• R represents hydrogen, C ⁇ -C 4 -alkoxycarbonyl or (C ⁇ -C4-alkoxycarbonyl) iminocarbonyl
• R 4 represents halogen
• R 5 COOH, -CC alkoxyiminomethyl, -C 4 alkoxy, C 3 -C 6 cycloalkyloxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 -Al- kenyloxyiminomethyl, (-C-C 4 -alkoxycarbonyl) -C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxyiminomethyl, 2- [C ⁇ -C 4 -alkoxycarbonyl] -2-chloroethyl, 2nd - [C ⁇ -C 4 -alkoxycarbonyl] -2-chloroethylene, -C-C 4 -alkoxycarbonyl, (Ci-C ⁇ -alkoxycarbonyl) -C ⁇ -C 4 -alkoxy, (C ⁇ -C 6 -alkoxycarbonyl) -C -C 4 -
• R 17 is C ⁇ -C-alkoxy and R 18 C ⁇ -C 4 -alkoxy or C ⁇ -C 4 -alkoxycarbonyl-C ⁇ -C 4 -alkoxy.
• Particularly preferred compounds of general formula la are the compounds listed in Table 1 la the first! to Ia x .206.
• substituted ureas of the formula Ib are particularly preferred, in particular the compounds Ib 1 . to Ib 1 .206, which differ from the corresponding compounds la 1. ! to Iai ⁇ O ⁇ differ only in that the N-substituents are inverse to each other:
• the compounds Ib 3 .l to Ib 3 .206 are further preferred, in which the variables Z, X, R 3 , R 4 and R 5 each have the meanings given in lines 1 to 206:
• the compounds are furthermore preferred lb .l 4 to 4 .206 Ib in which the variables Z, X, R 3, R 4 and R 5 each have the meanings given in the lines 1 to 206:
• the compounds are furthermore preferably 5 lb .l to .206 Ib 5, wherein the variables Z, X, R 3, R 4 and R 5 each have the meanings given in the lines 1 to 206th
• the compounds further preferred are 5 to .l Ib .206 5, wherein the variables Z, X, R 3, R 4 and R 5 each have the meanings given in the lines 1 to 206:
• the compounds Ib further preferably 7 to .l 7 .206 Ib in which the variables Z, X, R 3, R 4 and R 5 each have the meanings given in the lines 1 to 206:
• the compounds Ia are further preferably n .l to 11 .206 la, wherein the variables Z, X, R 3, R 4 and R 5 each have the meanings given in the lines 1 to 206:
• the compounds are furthermore preferably 12 lb .l to .206 Ib 12, wherein the variables Z, X, R 3, R 4 and R 5 each have the meanings given in the lines 1 to 206:
• the compounds are furthermore preferably 14 lb .l to .206 Ib 14, wherein the variables Z, X, R 3, R 4 and R 5 each have the meanings given in the lines 1 to 206:
• the compounds are furthermore preferably 15 lb .l to 15 Ib .206, rin WO variables Z, x, R 3, R 4 and R 5 each have the meanings given in the lines 1 to 206:
• the compounds are furthermore preferred lb 17 lb .l to 17 .206 in which the variables Z, X, R 3, R 4 and R 5 each have the meanings given in the lines 1 to 206:
• the compounds Ib further preferably 20 .l, R 3, R 4 and R 5 each have the meanings given in the lines 1 to 206 to 20 lb .206, where the variables x Z,:
• Ib.b 1 are also preferred! to Ib.b 1 224, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ib.b 2 l to Ib.b 2 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ib.b 3 l to Ib.b 3 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ia.b 4 l to Ia.b 4 224 are also preferred, where the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ib.bl to Ib.b 4 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ia.b 6 l to Ia.b 6 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ib.b further preferably 6 l to 6 Ib.b 224 wherein the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2:
• the compounds IA.B. further preferably 7 l to 7 IA.B. 224 wherein the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2:
• the compounds Ib.b further preferably 7 l to 7 Ib.b 224 WO-rin the variables X, Z, U and R 6 each have the meanings mentioned in rows 1 to 224 of Table 2:
• the compounds Ia.b 8 l to Ia.b 8 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ib.b 8 l to lb.b 8 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 15 224 of Table 2:
• the compounds Ia.b 10 l to Ia.b 10 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ib.b 10 l to Ib.b 10 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ib.b u l to lb.b n 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ia.b 12 l to Ia.b 12 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ib.b 12 l to Ib.b 12 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ib.b 13 l to Ib.b 13 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ib.b 14 l to lb.b 14 224 are furthermore preferred, in which the variables X, Z, U and R 6 each have the meanings given in rows 1 to 224 of Table 2:
• the compounds Ia.b 15 to 28 1 to Ia.b 15 to 28 224 which differ from the compounds Ia. Differentiate b 1 to 14 1 to Ia.b 1 to 14 224 only in that Y stands for S:
• the compounds Ib.c 1 are also preferred! to Ib.c 1 56, which differ from the compounds Ia.c 1 to Ia.c i ⁇ only in that the N substituents are inverse to one another:
• the compounds Ib.c 2 l to Ib.c 2 56 which differ from the compounds Ia.c 1 ! to la.c 1 56 differ only in that the N substituents are inverse to each other and R is C0 2 CH 3 :
• the compounds Ib.c 3 l to Ib.c 3 56 which differ from the compounds Ia.c 1 ! to Ia.c 1 56 differ only in that the N substituents are inverse to each other and R is C0 2 CH 3 and R 3 is Cl:
• the compounds Ib.c 4 l to Ib.c 4 56 which differ from the compounds Ia.c 1 ! to Ia.c x 56 differ only in that the N substituents are inverse to each other and R is CO 2 C 2 H 5 and R 3 is Cl:
• the compounds Ib.c 5 l to Ib.c 5 56 which differ from the compounds Ia.c 1 ! to Ia.c 1 56 differ only in that the N-substituents are inverse to each other and R is C (0) NHC0 2 CH 3 and R 3 is Cl:
• the compounds Ib.c 6 l to Ib.c 6 56 which differ from the compounds Ia.c 1 ! to Ia.c 1 56 differ only in that the N-substituents are inverse to each other and R is C (0) NHS0 2 CH 3 and R 3 is Cl: Also preferred are the compounds Ia.c 7 l to Ia.c 7 56, which differ from the compounds Ia.c 1 ! to Ia-c ⁇ ö differ only in that R is CO 2 CH 3 and R 3 is F:
• the compounds Ib.c 7 l to Ib.c 7 56 which differ from the compounds Ia.c 1 ! to Ia.c 1 56 differ only in that the N-substituents are inverse to each other and R is C0 2 CH 3 and R 3 are F:
• the compounds Ib.c 8 l to Ib.c 8 56 which differ from the compounds Ia.c 1 ! to Ia-c ⁇ ö differ only in that the N-substituents are inverse to each other and R is CO 2 C 2 H 5 and R 3 are F:
• the compounds Ib.c 9 l to Ib.c 9 56 which differ from the compounds Ia.c 1 ! to Ia.c x 56 differ only in that the N-substituents are inverse to each other and R is C (0) NHC0 2 CH 3 and R 3 is F:
• the compounds Ia.c 12 to 22 1 to Ia.c 12 to 22 56 which differ from the compounds Ia.c 1 to 1 to Ia.c 1 to 13 -56 only in that Y is S. ;
• the compounds Ib.c 12 to 22 1 to Ib.c 12 to 22 56 which differ from the compounds Ia.c 1 to n 1 to Ia.c 1 to 56 only in that the N substituents are inverse stand to each other and Y stands for S:
• the compounds Ib .c 23 to 33 1 to Ib.c 23 to 33 56 which differ from the compounds Ia.c 1 to 1 to Ia.c 1 to 1 X 56 only in that the N substituents stand inverse to each other and X stands for 0:
• the compounds Ib.c 34 to 44 1 to Ib.c 34 to 44 56 which differ from the compounds Ia.c 1 to 1 X 1 to Ia.c 1 to 11 56 only in that the N- Substituents are inverse to each other and Z stands for S:
• the compounds Ib.d 1 are also preferred! to Ib.d 1 35, which differ from the compounds Ia.d 1 ! to la.d 1 35 differ only in that the N-substituents are inverse to each other:
• the compounds Ib.d 2 l to Ib.d 2 35 which differ from the compounds Ia.d 1 ! to Ia.d ⁇ ⁇ differ only in that the N-substituents are inverse to each other and R is C0 2 CH 3 :
• the compounds Ib.d 3 l to lb.d 3 35 which differ from the compounds Ia.d 1 ! to Ia.d 1 35 only differ in that the N substituents are inverse to each other and R is C0 2 CH 3 and R 3 is Cl:
• the compounds Ib.d 4 l to Ib.d 4 35 which differ from the compounds Ia.d 1 ! to Ia.d ⁇ ⁇ only differ in that the N substituents are inverse to each other and R is C0 2 C 2 H 5 and R 3 are Cl:
• the compounds Ib.d 5 l to Ib.d 5 35 which differ from the compounds Ia.d x l to Ia.d ⁇ ⁇ only in that the N substituents are inverse to one another and R is C ( 0) NHC0 2 CH 3 and R 3 stand for Cl:
• the compounds Ib.d 6 l to Ib.d 6 35 which differ from the compounds Ia.d 1 ! to la.d 1 35 only differ in that the N substituents are inverse to each other and R is C (0) NHS0 2 CH 3 and R 3 is Cl:
• the compounds Ib.dl to Ib.d 7 35 which differ from the compounds Ia.d 1 ! to Ia.d 1 35 differ only in that the N-substituents are inverse to each other and R is C0 2 CH 3 and R 3 are F:
• the compounds Ib.d 8 l to Ib.d 8 35 which differ from the compounds Ia.d 1 ! only in different Ia.d to 1 .35 in that the N-substituents are inverse to each other and R is CO 2 C 2 H 5 and R 3 are F:
• the compounds Ib.d 9 l to Ib.d 9 35 which differ from the compounds Ia.d 1 ! to Ia.d 1 35 only differ in that the N substituents are inverse to each other and R is C (0) NHC0 2 CH 3 and R 3 is F:
• the compounds Ib.d 9 l to lb.d 9 35 which differ from the compounds Ia.d 1 ! to la.d 1 35 only differ in that the N substituents are inverse to each other and R is C (0) NHS0 2 CH 3 and R 3 is F:
• the compounds Ib.d 13 -1 to Ib.d 1: L 35 which differ from the compounds Ia.d 1 ! to Ia.d 1 35 only differ in that the N substituents are inverse to each other and R is C0 2 CH 3 , R 3 is F and Y is S:
• the compounds Ib.d 12 to 22 1 to Ib.d 12 to 22 35 which differ from the compounds ia.d 1 to u l to Ia.d 1 is 1] -35 only in that the N -Substituents are inverse to each other and X stands for O:
• the compounds Ib.d 23 to 33 1 to Ib.d 23 to 33 35 which differ from the compounds Ia.d 1 to u l to Ia.d 1 to 13 -35 only in that the N-- Substituents are inverse to each other and Z stands for S:
• substituted ureas are of the formula la.e 1
• the compounds Ib.e 1 are also preferred! to lb.e 1 35, which differ from the compounds la.e 1 1 to la.e 1 35 only in that the N substituents are inverse to one another:
• the compounds la.e 3 1 to la.e 3 35 which differ from the compounds la.e 1 1 to la.e 1 35 only in that R is C0 2 CH 3 and R 3 is Cl :
• the compounds Ib.e 3 l to Ib.e 3 35 which differ from the compounds la.e 1 1 to la.e 1 35 only in that the N substituents are inverse to one another and R is C0 2 CH 3 and R 3 stand for Cl:
• the compounds Ib.e 4 l to Ib.e 4 35 which differ from the compounds la.e 1 ! to Ia.e 1 35 only differ in that the N substituents are inverse to each other and R is C0 2 C 2 H 5 and R 3 is Cl:
• the compounds lb.e 5 l to lb.e 5 35 which differ from the compounds la.e 1 ! to Ia.e ⁇ ⁇ only differ in that the N substituents are inverse to each other and R is C (0) NHC0 2 CH 3 and R 3 is Cl:
• the compounds Ib.e 6 l to Ib.e 6 35 which differ from the compounds la.e 1 ! to Ia.e 1 35 differ only in that the N substituents are inverse to each other and R is C (0) NHS0 2 CH 3 and R 3 is Cl:
• the compounds lb.e 7 l to lb.e 7 35 which differ from the compounds la.e 1 ! to Ia.e ⁇ ⁇ only distinguish by the fact that the N substituents are inverse to each other and R is C0 2 CH 3 and R 3 is F:
• the compounds Ib.e 9 l to Ib.e 9 35 which differ from the compounds la.e 1 ! to Ia.e 1 35 differ only in that the N substituents are inverse to each other and R is C (0) NHC0 2 CH 3 and R 3 is F:
• the compounds Ia.e 10 l to Ia.e 10 35 which differ from the compounds la.e 1 ! to la.e 1 .35 only differ in that R is C (0) NHS0 2 CH 3 and R 3 is F:
• the compounds Ib.e 10 l to Ib.e 10 35 which differ from the compounds la.e 1 ! to Ia.e 1 35 only differ in that the N substituents are inverse to each other and R is C (0) NHS0CH 3 and R 3 is F:
• the compounds Ib.e n 1 to Ib.e 1] -35 which differ from the compounds la.e 1 ! to Ia.e 1 35 differ only in that the N substituents are inverse to each other and R is C0 2 CH 3 , R 3 is F and Y is S:
• compounds la.e 12 to 22 1 to la .e 12 to 22 35 which differ from compounds la .e 1 to n 1 to la .e 1 to n 35 only in that X is O. :
• Compounds la are also preferred. e 12 to 22 1 to la. e 12 to 22 35, which differ from the compounds la .e 1 to n l to la. E 1 is 1: 1 35 differ only in that the N substituents are inverse to each other and X is O:
• the compounds la.e 23 to 33 1 to la.e 23 to 33 35 which differ from the compounds la.e 1 to n l to la.
• the only difference between e 1 and n 35 is that Z stands for S;
• compounds la.e 23 to 33 1 to la.e 23 to 33 35 which differ from compounds la.e 1 to n l to la.e 1 to 13 -35 only in that the N- Substituents are inverse to each other and Z stands for S:
• the compounds Ib.f 2 l to Ib.f 2 21, which differ from the compounds la.f 1 ! to la.f 1 21 differ only in that the N-substituents are inverse to each other and R is C0 2 CH 3 :
• the compounds Ib.f 5 l to Ib.f 5 21, which differ from the compounds la.f 1 ! to Ia.f 1 21 differ only in that the N-substituents are inverse to each other and R is C (0) NHC0 2 CH 3 and R 3 is Cl:
• connections la.f 8 l to Ia.f 8 21, which differ from the connections la.f 1 ! to la.f 1 .21 differ only in that R is CO 2 C 2 H 5 and R 3 is F:
• the compounds Ib.f 8 l to Ib.f 8 21, which differ from the compounds la.f 1 ! to la.f 1 .21 differ only in that the N substituents are inverse to each other and R is CO 2 C 2 H 5 and R 3 are F:
• N- (2-hydroxyethyl) -N-amino-N known from WO 94/10173 and the more recent German patent application 198 29 745.9 can be used, for example, in accordance with Scheme 1 'acyl ureas with formaldehyde, for example convert aqueous formaldehyde solution to the N-methylimino-N- (2-hydroxyethyl) -N'-acylureas and then cyclize them in the presence of catalytic amounts of acid or a surface-active metal oxide to give the compound of the invention.
• WO 94/10173 the more recent patent application.
• N-substituted perhydrodiazines Ilb can also be reacted with an isocyanate or isothiocyanate III to give the end products Ib according to the following scheme: sc
• the reaction conditions and the implementation of the processes are described below with reference to the preparation of the ureas la and Ib substituted on the second ring nitrogen; however, the information can be applied to the preparation of all compounds of the formula Ia and Ib, in which R is hydrogen.
• the solvents used for these reactions are hydrocarbons such as pentane, hexane, heptane, cyclohexane, aromatics, e.g. benzene, toluene, xylene, heteroaromatics, e.g. pyridine, ⁇ , ⁇ , ⁇ -picoline and quinoline, chlorinated hydrocarbons, e.g.
• ethers such as 1,4-dioxane, 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 DMF, N, methylpyrrolidone
• Nitro hydrocarbons such as nitromethane, nitroethane, nitropropane and nitrobenzene, ureas such as tetraethyl urea, tetrabutyl urea,
• the hydrolysis of the substituted urea Ib in Scheme 6 is also conveniently carried out with an excess of water, e.g. carried out in aqueous solution.
• the concentration of the starting materials in the solvent is generally 0.1 to 5 mol / 1, preferably 0.2 to 2 mol / 1.
• the reaction of the N-amino-N'-arylureas according to Scheme 1 with formaldehyde or paraformaldehyde is advantageously carried out in the presence of a solvent at temperatures in the range from 0 to 150 ° C., preferably 10 to 100 ° C., particularly preferably 20 to 60 ° C. ,
• Aqueous formaldehyde preferably as an approximately 37% solution, is advantageously added over a period of 2 to 20 min to a mixture of the N-amino-N'-arylurea in one of the abovementioned solvents at 10 to 25 ° C., and 0 is then stirred to complete the reaction , 5 to 12 hours, preferably 1 to 3 hours at 20 to 60 ° C after.
• the N-amino-N'-arylurea can also be added to a mixture of formaldehyde in one of the abovementioned solvents and the reaction can then be completed as above.
• aqueous formaldehyde paraformaldehyde can also be used. It is generally not necessary to remove the water of reaction; however, the water of reaction can also be separated off via a water separator during the reaction.
• the reaction with formaldehyde according to step 1 in scheme 1 is preferably carried out with the exclusion of acidic catalysts, ie in a neutral to slightly alkaline medium.
• new acidic impurities are tralized by adding basic compounds, for example alkali metal or alkaline earth metal hydroxides or hydrogen carbonates or carbonates.
• organic bases can also be added or a basic solvent component such as pyridine can be used.
• the reaction can be carried out continuously or discontinuously under pressure or under pressure.
• the cyclization of the N-methylenimino-N'-arylureas to the 4- (arylcarbamoyl) tetra-hydro-4H-l, 3,4-ox (or thia) diazines is generally carried out with the addition of 1 to 100 % By weight of an acid, based on the urea, advantageously in the presence of one of the abovementioned solvents, at temperatures in the range from 0 to 150 ° C., preferably 10 to 120 ° C., particularly preferably 20 to 80 ° C.
• Aromatic sulfonic acids e.g. Benzenesulfonic acid, p-chloro- or p-toluenesulfonic acid, aliphatic sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, ethanesulfonic acid and n-propylsulfonic acid, sulfamic acid such as methylsulfamic acid, ethylsulfamic acid or isopropylsulfamic acid, aliphatic carboxylic acid, propyl acetic acid such as acetic acid or isobutyric acid and inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid or boric acid.
• the N-methyleneimino-N'-arylurea is advantageously added to the organic acid, preferably acetic acid as reaction medium, over a period of 2 to 20 minutes at 10 to 25 ° C., and stirring is continued for 0.5 to 12 hours, preferably 1 to 3 hours 20 to 80 ° C after.
• the acid can also be added directly to the reaction solution of the N-methylenimino-N'-arylurea stage formed from N-amino-N'-arylurea and formaldehyde and this can be added to the 4- without isolation, if necessary after distilling off a solvent part. Cyclize (arylcarbamoyl) tetrahydro-4H-l, 3,4-ox (or thia) diazine.
• the concentration of the starting materials in the solvent is generally 0.1 to 5 mol / 1, preferably 0.2 to 2 mol / 1.
• a neutral or acidic surface-active metal oxide for example aluminum oxide, iron oxide, boron oxide, silicon dioxide, titanium dioxide, arsenic oxide, antimony oxide, chromium oxide or manganese oxide, can also be used as the catalyst.
• reaction can be operated without pressure or under pressure, continuously or batchwise. If R is hydrogen, the compounds of the general formulas la or ib can be cyclized to give bicyclic triazolinediones in analogy to known processes (Scheme la).
• the phosgene is advantageously passed at 10 to 60 ° C. with stirring into a mixture of a 4- (phenylcarbamoyl) tetrahydro-4H-l, 3,4-ox (or thia) diazine and an amount of 0.5 to 5% by weight .-%, based on the starting material, activated carbon as a catalyst in one of the aforementioned anhydrous solvents for 0.5 to 20 hours, preferably 1 to 12 hours.
• the reaction can additionally be accelerated by a basic amide catalyst, e.g. DMF, which can usually be used in an amount of 0.3 to 10 wt .-% based on the input material.
• a basic amide catalyst e.g. DMF
• Organic bases such as triethylamine, tri-n-propylamine, N, N-dimethylaniline or N, N-dimethylcyclohexylamine can also be used as the basic catalyst.
• Pyridine can also preferably be used, if appropriate directly as a solvent.
• diphosgene can also be used.
• the diphosgene is advantageously added to the mixture of the starting material and one of the abovementioned solvents, with or without the addition of activated carbon, DMF or the organic base, with stirring at 0 to -5 ° C. over a period of 1 hour Warm 10 ° C and then stir at 10 to 60 ° C for 1 to 12 hours.
• the molar amount of phosgene or diphosgene is 0.98 to 5, preferably 1 to 3, particularly preferably 1 to 1.3 per mol of starting material.
• the concentration of the starting materials in the solvent is generally 0.1 to 5 mol / 1, preferably 0.2 to 2 mol / 1.
• the reaction can be carried out under pressure or under pressure, continuously or batchwise.
• the multistage reaction according to Scheme 1 and Ia can also advantageously be carried out as a one-pot process, the water of reaction which is formed in the first synthesis step in the reaction of the N-amino-N'-phenylureas being removed with formaldehyde
• N-methylenimino-N'-phenylureas with the addition of a neutral or acidic catalyst to the 4- (phenylcarbamoyl) tetrahydro-4H-l, 3,4-ox (or thia) diazines cyclized and then optionally with phosgene or Diphosgene, if appropriate with the addition of activated carbon or an amide catalyst or in the presence of a base, is cyclized to give the end products la '. If appropriate, acidic catalysts present are separated off before the phosgency clization by phase separation or distillation and the ring closure is then carried out to give the triazolinediones IV.
• the intermediates are taken up in a water-immiscible solvent, acidic impurities are extracted with dilute alkali metal or water, dried and the solvent is removed under reduced pressure.
• an isocyanate or isothiocyanate III is advantageously added to a mixture of the perhydrodiazine Ila or Ilb in one of the abovementioned solvents at 10 to 25 ° C. for 5 to 30 min and then stirred to complete the reaction for 0.5 to 24 Hours, preferably 1 to 10 hours at 20 to 80 ° C after.
• the isocyanate or isothiocyanate III can also be introduced in one of the abovementioned solvents, the N-substituted perhydrodiazine added and the reaction then completed as above.
• the nucleophile is advantageously added to a mixture of the triazolinedione IV in one of the abovementioned solvents at 10 to 30 ° C. for 5 to 30 min and then stirred to complete the Reaction after 0.5 to 24 hours, preferably 1 to 10 hours at 20 to 60 ° C after.
• the triazolinedione IV can also be added to a mixture of the nucleophile in one of the aforementioned solvents and then complete the reaction as above.
• the alcohols or thiols of the formula V are expediently used in the form of their alkali metal or alkaline earth metal salts, that is to say their lithium, sodium, potassium, magnesium or calcium salts.
• the reaction can also be carried out in the presence of an organic base e.g. Triethylamine, tri-n-propylamine, N-ethyldiisopropylamine, pyridine, ⁇ -, ß-, ⁇ -picoline, 2,4-, 2,6-lutidine, N-methylpyrrolidine, triethylene diamine, dimethylaniline, N, N -Dimethylcyclohexylamine, quinoline or acridine.
• an organic base e.g. Triethylamine, tri-n-propylamine, N-ethyldiisopropylamine, pyridine, ⁇ -, ß-, ⁇ -picoline, 2,4-, 2,6-lutidine, N-methylpyrrol
• Salt formation can also be carried out with an alkali or alkaline earth hydride or hydroxide.
• the alcohols or thiols are converted into their corresponding salts with one of the abovementioned bases in an inert solvent and then the reaction with the triazolinedione is followed.
• the water formed during salt formation can be left in the reaction medium or removed azeotropically with a solvent.
• the salt formation can also be carried out from the outset in an aqueous phase and then the water can be removed.
• salt formation can also be carried out with an alkali or alkaline earth alcoholate, preferably sodium methylate or ethylate, and excess alcohol oil can be removed before the reaction with the triazolinedione, or the solvent can be used directly in the same alcohol.
• an alkali or alkaline earth alcoholate preferably sodium methylate or ethylate
• excess alcohol oil can be removed before the reaction with the triazolinedione, or the solvent can be used directly in the same alcohol.
• the bases mentioned in the explanations for Schemes 3 and 3a can be used as the base, preferably organic bases such as triethylamine or pyridine.
• organic bases such as triethylamine or pyridine.
• an alkali or alkaline earth metal hydride preferably sodium or potassium hydride
• reaction of la 'or Ib' with the acid derivatives IX according to Scheme 5 or 6 can also be carried out in a two-phase system in the presence of a phase transfer catalyst.
• Quaternary ammonium or phosphonium salts can be used as phase transfer catalysts.
• A stands for a leaving group such as halogen, for example fluorine, chlorine or bromine, preferably chlorine, in the case of C (0) R 2 for an oxy-Ci-C ⁇ -alkanoyl-oxy-C 3 -C 6 -alkenoyl - Or oxy-C 3 -C 6 -alkinoylrest and in the case of formyl for an oxy-Ci-Ce-alkanoylrest.
• halogen for example fluorine, chlorine or bromine, preferably chlorine
• Substituted ureas la or Ib are available as starting material, in which R is an easily removable radical such as C (0) 0R 10 , C (S) 0R 10 , C (S) SR 10 , C (0) SR 10 , C0 2 H or CHO (urea Ib - Scheme 6), this radical R can be split off according to Scheme 6 by hydrolysis with water, advantageously in the presence of a base at 10 to 100 ° C., advantageously 20 to 80 ° C.
• the base is advantageously used in a molar ratio of 0.9 to 1.4, preferably 0.95 to 1.2, particularly preferably 0.98 to 1.15 for the ratio of substituted urea Ib to base.
• the bases mentioned can be used as bases, preferably alkali or alkaline earth hydroxide, particularly preferably sodium hydroxide.
• the substituted ureas Ia and Ib can be prepared by the above-mentioned synthetic method according to the invention.
• 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, distributing the residue in a mixture of water and a suitable one organic solvents and working up the organic phase towards the product.
• oxazine derivatives of the general formula Ila used as starting compounds according to Scheme 2 are new and the subject of a parallel application. They are prepared, for example, by first using a substituted hydrazine of the formula X
• Suitable, nucleophilically displaceable leaving groups are halogen, preferably chlorine or bromine, C 1 -C 6 -alkoxy such as methoxy, ethoxy, n-propoxy, n-butoxy, C 1 -C 4 -haloalkoxy such as trichloromethoxy, trifluoromethoxy, pentafluoroethoxy, N- bonded heterocyclyl such as imidazolyl, Ci-C ⁇ -alkylcarbonyloxy (or Ci-C ⁇ -alkanoate) such as acetate, propionate, n-butyrate, isobutyrate, pivalate and capronate, C 1 -C 6 -haloalkylcarbonyloxy such as mono-, di- and Trichloroacetate, -CC 6 alkylsulfonyloxy such as methylsulfonyloxy, Ci-C ö -haloalkylsulfonyloxy such as trifluor
• Preferred leaving group is halogen, in particular chlorine or bromine, and also acetate or trifluoroacetate.
• the cyclization of the second production step can take place either with formaldehyde or with a compound which releases formaldehyde under acidic conditions, such as paraformaldehyde or 1,3,5-trioxane, in the presence of an acid.
• the hydrazides obtained in the first production step can also be reacted with formaldehyde to form the Schiff base and then the cyclization can be effected by adding an acid.
• the preparation of the compounds Ila is exemplified by the reaction described in the following scheme, starting from 2-hydrazinoethanol and methyl chloroformate as acid derivative, the N-amino-N-methoxycarbonyl-2-hydrazinoethanol is first prepared, which is then reacted with formaldehyde Tetrahydro-4-methoxycarbonyl-4H-1-oxa-3,4diazine is cyclized.
• the reaction of the hydrazinoethanols / thiols X with the acid derivatives RA is advantageously particularly preferred in the presence of a solvent at temperatures in the range from -30 to 100 ° C., preferably -10 to 80 ° C. 0 to 60 ° C carried out.
• the solvents used for these reactions are hydrocarbons such as pentane, hexane, cyclopentane, cyclohexane, toluene, xylene, chlorinated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, 1,1,2,2-Te - Trachloroethane, chlorobenzene, 1,2-, 1,3- or 1,4-dichlorobenzene, ethers such as 1,4-dioxane, 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 DMF, N-methylpyrrolidone, nitro hydrocarbons such as nitrobenzene, ureas such as tetrae
• hydrocarbons such
• the molar ratios in which the starting compounds X and IX are reacted with one another are generally 0.9 to 1.2, preferably 0.95 to 1.1, particularly preferably 0.98 to 1.04 for the ratio of acid derivative of general formula IX to
• the first reaction step is advantageously carried out under neutral conditions. If an acidic reaction product is formed during the reaction, e.g. Hydrogen halide when A in formula IX is halogen is removed by adding basic compounds, e.g. B. alkali or alkaline earth metal hydroxides or hydrogen carbonates or carbonates. However, the reaction can also be carried out in the presence of an organic base, e.g. B.
• reaction can also be carried out in an aqueous two-phase system, preferably in the presence of phase transfer catalysts such as quaternary ammonium or phosphonium salts.
• phase transfer catalysts such as quaternary ammonium or phosphonium salts.
• the acid derivative IX is advantageously added over a period of 0.25 to 2 hours to a mixture of the hydrazinoethanol / thiols X and the base in one of the abovementioned solvents at 0 to 60 ° C. and the mixture is stirred for a further 0.5 to 16 hours, preferably 2 to 8 hours to 0 to 60 ° C after.
• the starting materials X and IX can be added in any order to a mixture of the phase transfer catalyst in the two phases with stirring and then the reaction can be completed in the temperature range mentioned with the addition of base.
• the reaction can be carried out continuously or discontinuously under pressure or under pressure.
• the salts which may have precipitated are separated off, or their separation is completed by adding non-polar solvents and the hydrazides are thus enriched in the filtrate.
• the second reaction step is explained below:
• the hydrazides are then advantageously reacted under acidic conditions with a formaldehyde solution or paraformaldehyde in one of the abovementioned solvents.
• 0.9 to 1.2, preferably 0.95 to 1.1, particularly preferably 0.98 to 1.04, mole equivalents of formaldehyde or paraformaldehyde are advantageously used per mole of hydrazide derivative.
• the concentration of the starting materials in the solvent is 0.1 to 5 mol / 1, preferably 0.2 to 2 mol / 1.
• Aromatic sulfonic acids e.g. Benzenesulfonic acid, p-chloro- or p-toluenesulfonic acid, aliphatic sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, ethanesulfonic acid and n-propylsulfonic acid, sulfamic acids such as methylsulfamic acid, ethylsulfamic acid or isopropylsulfamic acid, aliphatic carboxylic acid such as acetic acid, butobetic acid, trifluoric acid, trifluoric acid and use inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid or boric acid.
• aliphatic sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, ethanesulfonic acid and n-propyls
• the acidic catalyst is advantageously used in an amount of 1 to 20 mol%, preferably 3 to 15 mol%, particularly preferably 5 to 10 mol%, of acid per mol of hydrazide.
• a formaldehyde solution or paraformaldehyde is preferably added to a mixture of hydrazide and the acid catalyst in one of the abovementioned solvents at from 0 to 100 ° C., advantageously from 10 to 80 ° C., particularly preferably from 20 to 50 ° C., and the mixture is stirred Completion of the reaction after 10 to 50 hours, preferably 15 to 30 hours at 40 to 50 ° C.
• the water is expediently removed, e.g. on the water separator.
• the acidic catalyst can also be added to a mixture of hydrazide and paraformaldehyde in one of the abovementioned solvents and the reaction can then be brought to an end as described.
• the reaction can be operated without pressure or under pressure, continuously or batchwise.
• Oxidation with hydrogen peroxide can be catalyzed by suitable metal compounds, for example transition metal oxides such as vanadium pentoxide, sodium tungstate, potassium dichromate, iron oxide tungsten framat, sodium tungstate molybdic acid, osmic acid, titanium trichloride, selenium dioxide, phenylene selenic acid, oxovanadinyl-2,4-pentanedionate.
• the catalysts are generally used in an amount of 0.5 to 10%, but because of the easy filterability and recovery of the inorganic catalysts, stoichiometric amounts can also be used.
• solvents for the oxidation with hydrogen peroxide are water, acetonitrile, alcohols such as methanol, ethanol, isopropanol, tert-butanol, chlorinated hydrocarbons such as methylene chloride, 1, 1,2,2-tetrachloroethane or ketones such as acetone or methyl ethyl ketone be used.
• peracids such as perbenzoic acid, monoperphthalic acid or 3-chloroperbenzoic acid can also be used as the oxidizing agent.
• the reaction with peracids is conveniently carried out in chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane.
• Chlorine and bromine are also very suitable for the oxidation of the thiols to sulfoxides or sulfones.
• This oxidation is expediently carried out in polar solvents such as water, acetonitrile, dioxane, or in two-phase systems such as aqueous potassium hydrogen carbonate solution / dichloromethane and also acetic acid.
• polar solvents such as water, acetonitrile, dioxane, or in two-phase systems
• aqueous potassium hydrogen carbonate solution / dichloromethane and also acetic acid Tert-butyl hypochlorite, hypochlorous and hypobromous acid, their salts, furthermore N-halogen compounds such as N-bromine and N-chlorosuccinimide or also sulfuryl chloride can also be used as a source of active halogen.
• Photosensitized oxygen transfer is also suitable for the oxidation, with organic dyes, e.g. Porphyrins such as tetraphenylporphyrin, chlorophyll, protoporphyrin, xanthene dyes such as rose bengal or phenothiazine dyes such as methylene blue are used.
• organic dyes e.g. Porphyrins such as tetraphenylporphyrin, chlorophyll, protoporphyrin, xanthene dyes such as rose bengal or phenothiazine dyes such as methylene blue are used.
• inert solvents are hydrocarbons such as pentane, hexane, heptane, cyclohexane, chlorinated hydrocarbons such as methylene chloride, 1,2-dichloroethane, 1, 1,2,2-tetrachloroethane, alcohols such as methanol, ethanol, n-propanol or isopropanol, ketones such as acetone , Methyl ethyl ketone, polar aprotic solvents such as
• Acetonitrile, propionitrile or aromatic hydrocarbons such as benzene, toluene, chlorobenzene or xylene are suitable.
• oxygen it is also possible to use ozone in the abovementioned solvents, in addition to ether, 1,4-dioxane or THF.
• catalysts such as oxides and sulfides of nickel, copper, aluminum, tungsten, chromium, vanadium, ruthenium, titanium, manganese, molybdenum, magnesium and iron are also suitable for oxygen oxidation.
• the molar ratios in which the starting compounds are reacted with one another are generally 0.9 to 1.8, preferably 1.05 to 1.3 for the ratio of tetrahydrothiadiazine to oxidizing agent in the case of oxidation to sulfoxide and generally 1 , 9 to 3.5, preferably 2.05 to 2.9 in the case of oxidation to the sulfone.
• the concentration of the starting materials in the solvent is generally 0.1 to 5 mol / 1, preferably 0.2 to 2 mol / 1.
• the addition and reaction temperature depend on the optimal efficiency of the respective oxidizing agents and the avoidance of side reactions. If photosensitized oxygen is used, the process is generally carried out at from -20 to 80.degree. C., but is generally metal-catalyzed at from 50 to 140.degree. C. and, when using ozone, generally at -78 to 60.degree.
• these are preferably introduced continuously into the reaction mixture over a relatively long period of time (up to 20 hours) until the oxidation at the sulfoxide or sulfone stage is complete.
• Liquid or easily soluble oxidizing agents such as hydrogen superoxide, hypochlorous or bromine acid, tert-butyl hypochlorite, chlorine or bromine, furthermore N-chloro- or N-bromosuccinimide can, depending on the exothermic nature of the reaction, in shorter time spans from 0.25 to 6 hours are added to the reaction mixture of the thiadiazine or sulfoxide to bring the reaction to a conclusion after a further 1 to 60 h.
• a staggered addition of the liquid or dissolved oxidizing agent is also preferred.
• hydrogen superoxide one generally works at 0 to 90 ° C. with tert. -Butylpypochlorite in general at -78 to 30 ° C and with N-halogen compounds in general at 0 to 30 ° C.
• a reaction temperature of 0 to 40 ° C is recommended.
• the oxidations can be operated without pressure, under pressure, continuously or batchwise.
• the reaction product 1 a is allowed to cool to 90 to 20 ° C., a solvent, for example methylene chloride and / or water, is optionally added, and the oxidizing agent is then added in accordance with its consumption. Hydrogen peroxide or sodium hypochlorite are particularly preferred as oxidizing agents.
• the end products Ila are generally taken up in a water-immiscible solvent, acidic impurities or oxidizing agents are extracted with dilute alkali metal or water, dried and the solvent is removed under reduced pressure.
• n D refractive index at 23 ° C v [cm -1 ] IR bands Table b)
• n D 23 refractive index at 23 ° C
• Example 1 (Compound Ib, No. 1, Table 7)
• Tetrahydro-N- (2,4-dichloro-5-methoxy-phenyl) -4H-1,3,4-oxdiazine-3-carboxamide-4-carboxylic acid methyl ester 0.3 g (1.666 mmol) of 30% sodium methylate was added to a solution of 0.5 g (1.505 mmol) of 8- (2 ', 4'-dichloro-5'-methyloxyphenyl) -4-oxa- 7,9-dioxo-l, 2,8-triaza (4.3.0) nonane in 50 ml of methanol. The mixture was stirred at 22 ° C. for a further 6 h.
• reaction mixture was concentrated in vacuo and partitioned between methylene chloride and 1N hydrochloric acid. After drying the organic phase over magnesium sulfate and concentrating in vacuo, 0.5 g (88.5% of theory) of the title compound was obtained as colorless crystals, mp. 160-163 ° C.
• N '- [4' -chloro-2 '-fluoro-5' - (methoxyiminomethyl) phenyl] urea prepared according to Example la of DE 198.29.745.9, added to 100 ml of 1,2-dichloroethane and stirred at 83 ° C. for 2 h , After cooling, the mixture was worked up extractively in water and, after removal of the solvent, 1.3 g of N-methylenimino-N-2-chloro thyl-N '- [4' -chloro-2 '-fluoro-5' - (methoxyiminomethyl) phenyl] urea with a fixed point of 120-122 ° C.
• the compounds Ia and Ib 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 Ia and Ib very well control plant growth on nonculture areas, particularly at high application rates. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
• the compounds Ia or Ib or compositions containing them can also be used in a further number of crop plants for eliminating undesirable plants.
• the following crops are considered, for example:
• the compounds Ia and Ib 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 substances 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 compounds grow more rapidly on the leaves below unwanted plants or the uncovered floor area (post-directed, lay-by).
• the compounds Ia or Ib or the herbicidal compositions comprising them can be carried out, 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, sprinkling agents or granules Spraying, atomizing, dusting, scattering or pouring can be used.
• the application forms depend on the intended use; 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, also 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 cyclohexanone or strongly polar solvents, e.g. B. amines such as N-methylpyrrolidone or water.
• mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin
• aliphatic, cyclic and aromatic hydrocarbons e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, al
• Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
• the substituted ureas as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
• wetting agents adhesives, dispersants or emulsifiers.
• it can also consist of an active substance, wetting agent, adhesive agent, dispersant or emulsifier and possibly concentrates made up of solvents or oil that 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 naphthalene Derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl
• 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, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
• the concentrations of the active substances la and Ib in the ready-to-use preparations can be varied within wide limits.
• 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 Ia and Ib according to the invention can be formulated, for example, as follows:
• I 20 parts by weight of compound Ib.6 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 moles of ethylene oxide and 1 mole 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 and 1 mole of castor oil.
• aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
• V 3 parts by weight of active ingredient Ib.6 are mixed with 97 parts by weight of finely divided kaolin. In this way, a dust is obtained which contains 3% by weight of the active ingredient.
• the substituted ureas la and Ib can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together.
• the compounds Ia or Ib alone or in combination with other herbicides, mixed with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria.
• the miscibility with mineral salt solutions which are used to remedy nutritional and trace element deficiencies.
• Non-phytotoxic oils and oil concentrates can also be added.
• the active compound application rates are from 0.01 to 3, preferably 0.1 to 1.0 kg / ha of active substance (see also).
• Plastic 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 tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic covers 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 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 post-emergence treatment was 62.5, 31.3 or 16.6 and 7.81 g / ha a. S.
• the plants were kept in a species-specific manner at temperatures of 10 to 25 ° C and 20 to 35 ° C.
• the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
• the compounds can be used to combat undesirable broad-leaved plants very well in the post-emergence process.
• Test plants ABUTH 100 100
• Test plants ABUTH 100 100
• Test plants ABUTH 100 100

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• 2000
  • 2000-06-23 AU AU59772/00A patent/AU5977200A/en not_active Abandoned
  • 2000-06-23 EA EA200200040A patent/EA200200040A1/ru unknown
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  • 2000-06-23 EP EP00945805A patent/EP1187820A1/de not_active Withdrawn
  • 2000-06-23 BR BR0011893-1A patent/BR0011893A/pt not_active Application Discontinuation
  • 2000-06-23 JP JP2001507011A patent/JP2003503398A/ja not_active Withdrawn
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