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EP1303498A1 - Substituted 2-amino-1,3,5-triazines, and the use thereof as herbicides and plant growth regulators - Google Patents

Substituted 2-amino-1,3,5-triazines, and the use thereof as herbicides and plant growth regulators

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Publication number
EP1303498A1
EP1303498A1 EP01947437A EP01947437A EP1303498A1 EP 1303498 A1 EP1303498 A1 EP 1303498A1 EP 01947437 A EP01947437 A EP 01947437A EP 01947437 A EP01947437 A EP 01947437A EP 1303498 A1 EP1303498 A1 EP 1303498A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
substituted
radicals
unsubstituted
alkylamino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01947437A
Other languages
German (de)
French (fr)
Inventor
Wolfgang Giencke
Lothar Willms
Thomas Auler
Hermann Bieringer
Hubert Menne
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1303498A1 publication Critical patent/EP1303498A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines

Definitions

  • the invention relates to the technical field of crop protection agents, such as herbicides and plant growth regulators, in particular herbicides for the selective control of harmful plants in crops of useful plants.
  • crop protection agents such as herbicides and plant growth regulators, in particular herbicides for the selective control of harmful plants in crops of useful plants.
  • the known active ingredients sometimes have disadvantages when used, whether it is inadequate herbicidal activity against harmful plants, too small a range of harmful plants which can be combated with an active ingredient, or insufficient selectivity in crops of useful plants.
  • Other active ingredients cannot be produced economically on an industrial scale because of the difficult to access precursors and reagents, or they have insufficient chemical stability.
  • the object of the invention is to provide alternative active compounds of the 2-amino-1,3,5-triazine type, which can optionally be used with advantages as herbicides or plant growth regulators.
  • the present invention relates to compounds of the formula (I) and their salts,
  • R 1 aryl, aryloxy, arylthio, arylamino, N-aryl-N- (-C-C 4 ) alkyl-amino, (C 3 - C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyloxy, (C 3 -C 9 ) Cycloalkylthio, (C 3 - Cg) cycloalkylamino, N- (C 3 -C 9 ) cycloalkyl-N- (CrC 4 ) alkylamino, di - [(C 3 - C 9 ) cycloalkyl] amino, heterocyclyl, heterocyclyloxy , Heterocyclylthio, Heterocyciylamino or N-heterocyclyl-N- (CrC 4 ) alkyl-amino, where each of the latter 16 residues is unsubstituted or substituted, preferably unsubstituted
  • alkylamino carbonyl (-C-C 6 ) alkylsulfonyl and (CC 6 ) haloalkylsulfonyl is substituted and including substituents preferably has up to 30 C atoms, or
  • L 1 is a direct bond, -O-, -S- or a group of the formula -NG 2 -, preferably a direct bond,
  • U 3 is a group of the formula G 13 , OG 14 , SG 15 , NG 16 G 17 , NG 18 NG 19 G 20 ,
  • U 4 is a group of the formula G 25 , OG 26 , SG 27 or NG 28 G 29 , where the radicals G 1 to G 29 independently of one another are hydrogen, aryl which is unsubstituted or substituted and preferably has 6 to 30 C atoms including substituents, or (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted and preferably including substituents Has 3 to 30 carbon atoms, or heterocyclyl, which is substituted or unsubstituted and including substituents preferably has 2 to 30 carbon atoms, or (-C-C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 - C 6 ) mean alkynyl, where each of the latter 3 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, nitro, thiocyanato, (C 1 -C 4 ) alkoxy, (
  • R ', R "and R'” each independently of one another are hydrogen or preferably (CC 6 ) alkyl, aryl, aryl- (CrC 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 -C 9 ) cycloalkyl- ( C 1 -C 6 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, and in which Z and T are each independently an oxygen or sulfur atom / is substituted and preferably contains 1 to 30 C atoms, including substituents, or the Residues U 1 and U 3 or U 2 and U 4 or U 2 and G 1 or U 4 and G 1 in pairs with the atoms connecting them each represent a carbocyclic or heterocyclic ring with 4 to 7 ring atoms, the ring being unsubstituted or substituted is a radical of the formula -B 1 -D 1 , where B 1 and D 1 are
  • a 2 is a direct bond or straight-chain alkylene having 1 to 4 carbon atoms or straight-chain alkenylene or alkynylene each having 2 to 5 carbon atoms, each of the three last-mentioned diradicals being unsubstituted or by one or more radicals from the group halogen, nitro, cyano , Thiocyanato and radicals of the formula -B 3 -D 3 is substituted, or a divalent radical of the formula V 1 , V 2 , V 3 , V 4 or V 5 ,
  • each of the radicals R a , R b , R c , R d , R e and R f each independently of one another is hydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula -B 4 -D 4 ,
  • W * is in each case an oxygen atom, a sulfur atom or a group of the formula N (B 5 -D 5 ) and
  • Hydrogen aryl which is unsubstituted or substituted and preferably has 6 to 30 C atoms including substituents, or (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted and preferably has 3 to 30 C atoms including substituents, or heterocyclyl , which is substituted or unsubstituted and including substituents preferably has 2 to 30 C atoms, or (-C-C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 unsubstituted radicals or by one or more radicals from the group halogen, hydroxy, cyano, nitro, thiocyanato, (C ⁇ -C 4) alkoxy, (C ⁇ -C 4) haloalkoxy, (C 2 -C 4) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (-
  • R ', R "and R'” each independently of one another are hydrogen or preferably (CC 6 ) alkyl, aryl, aryl- (C 1 -C 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (Cs-CgJCycloalkyKC-i- CeJalkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, and in which Z and Z 'are each independently an oxygen or sulfur atom, are substituted and, including substituents, preferably have 1 to 30 C atoms, (X) nn substituents X and X is independently halogen,
  • the compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, for example HCl, HBr, H 2 SO 4 or HNO 3 , but also oxalic acid or sulfonic acids to a basic group, such as amino or alkylamino.
  • Suitable substituents which are present in deprotonated form such as, for example, sulfonic acids or carboxylic acids, can form internal salts with groups which can be protonated, such as amino groups.
  • Salts can also be formed in that, in the case of suitable substituents, such as, for example, sulfonic acids or carboxylic acids, the hydrogen is replaced by a cation which is suitable for agriculture.
  • salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts.
  • the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and / or substituted radicals in the carbon skeleton can each be straight-chain or branched.
  • the lower carbon skeletons e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl etc., mean e.g.
  • Alkynyl means e.g. Propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-yl.
  • Cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 C atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • substituents having a double bond on the cycloalkyl radical e.g. B. an alkylidene group such as methylidene.
  • multi-cyclic aliphatic systems are also included, such as, for example, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, Bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, adamantan-1-yl and adamantan-2-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl.
  • substituted cycloalkenyl the explanations for substituted cycloalkyl apply accordingly.
  • Halogen means, for example, fluorine, chlorine, bromine or iodine.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
  • a heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic; it preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms.
  • Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and additionally oxo.
  • the oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example in the case of N and S.
  • Substituted radicals such as a substituted alkyl, alkenyl, alkynyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, mean, for example, a substituted radical derived from the unsubstituted basic body, the substituents being, for example, one or more, preferably 1, 2 or 3 radicals from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino , and Alkylsuifinyl, Haloalkylsulfinyi, Alkylsulfonyl, Haloalkylsulfonyl and, in the case of cyclic radicals, also
  • radicals from the group mean one or more identical or different radicals from the group of radicals mentioned, unless specific restrictions are expressly defined.
  • substituted radicals such as substituted alkyl etc. includes, in addition to the saturated hydrocarbon-containing radicals mentioned, corresponding unsaturated aliphatic and aromatic radicals, such as optionally substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy etc.
  • substituted cyclic radicals with aliphatic portions in the ring cyclic systems with such substituents are also included, which are bonded to the ring with a double bond, e.g. B. are substituted with an alkylidene group such as methylidene or ethylidene.
  • radicals with carbon atoms those with 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred.
  • the substituents methyl, methoxy and chlorine are particularly preferred.
  • Mono- or disubstituted amino means a chemically stable radical from the group of substituted amino radicals which are, for example, N-substituted by one or two identical or different radicals from the group alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles; alkyl radicals having 1 to 4 carbon atoms are preferred; Aryl is preferably phenyl or substituted phenyl; the definition given below applies to acyl, preferably (C 1 -C 4 ) alkanoyi. The same applies to substituted hydroxylamino or hydrazino.
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or one or more times, preferably up to three times, by the same or different radicals from the group halogen, (-C 4 -C) alkyl, (CrC 4 ) alkoxy, (-C 4 ) haloalkyl , (CrC 4 ) haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and trichlorophenyl, 2, 4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxy phenyl.
  • An acyl radical in a broad sense means the residue of an organic acid which is formally formed by removing an OH group, for example the residue of a carboxylic acid and residues of acids derived therefrom, such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the rest of carbonic acid monoesters, optionally N -substituted carbamic acid, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids.
  • Acyl means, for example, formyl, alkylcarbonyl such as [(C 1 -C 4 ) alkyl] carbonyl, phenylcarbonyl, alkyloxycarbonyl, Phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other residues of organic acids.
  • radicals in each case in the alkyl or phenyl part can be further substituted, for example in the alkyl part by one or more radicals from the group halogen, alkoxy, phenyl and phenoxy;
  • substituents in the phenyl part are the substituents already mentioned above generally for substituted phenyl.
  • acyl means, for example, the remainder of an alkanoic acid, alkenoic acid, alkynic acid, arylcarboxylic acid (e.g.
  • acyl means a residue of an alkanoic acid, e.g. B. a (CC 24 ) alkanoic acid, preferably (-C-C ⁇ s) alkanoic acid, in particular (CrC- ⁇ 2 ) alkanoic acid, very particularly (Ci-C ⁇ Jalkanoic acid such as formyl, acetyl or propionyl.
  • alkanoic acid e.g. B. a (CC 24 ) alkanoic acid, preferably (-C-C ⁇ s) alkanoic acid, in particular (CrC- ⁇ 2 ) alkanoic acid, very particularly (Ci-C ⁇ Jalkanoic acid such as formyl, acetyl or propionyl.
  • the general formulas can formally define unstable functional groups by combining variables, e.g. the carbamyl radical or the hydroxycarbonyloxy radical, which are unstable in the neutral or acidic aqueous medium and are therefore not preferred or are used only in the form of their stable salts or degradation products.
  • the invention also relates to all stereoisomers which are encompassed by formula (I) and mixtures thereof.
  • Such compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds which are not indicated separately in the general formulas (I).
  • the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I) and can be obtained from mixtures of the stereoisomers by customary methods or else by stereoselective reactions in combination with the use of stereochemically pure starting materials can be produced.
  • Compounds according to the invention are, especially for the reasons of the higher herbicidal activity, better selectivity and / or better manufacturability Formula (I) mentioned or its salts of particular interest, in which individual radicals have one of the preferred meanings already mentioned or mentioned below, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.
  • R 1 is preferably phenyl, phenoxy, phenylthio, phenylamino, N-phenyl-N- (C ⁇ - C) alkyl-amino, each of the latter 5 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro , Formyl, carboxy, sulfo, cyano, thiocyanato, (CrC 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (CC 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C ⁇ -C 4 ) alkylthio, ( C 1 -C 4 ) haloalkylthio, mono (C 1 -C 4 ) alkylamino, di (C ⁇ -C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C 1 -C 4 ) alkyl
  • R 1 is preferably also (C 3 -C 9 ) cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (CC 4 ) alkyl, (CC) haloalkyl, (CC 4 ) Alkoxy, (-C-C 4 ) haloalkoxy, (CC 4 ) alkylthio, (C ⁇ -C) haloalkylthio, mono (C ⁇ -C) alkylamino and di (C ⁇ -C) alkylamino is substituted and including substituents 3 to 30 C-atoms, preferably has 3 to 20 carbon atoms, in particular 3 to 15 carbon atoms.
  • R 1 is (C 3 -C 6 ) cycloalkyl which is unsubstituted or substituted.
  • R 1 is preferably also heterocyclyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (CrC 4 ) alkyl, (CrC) haloalkyl, (C ⁇ - C 4 ) alkoxy, (CC 4 ) haloalkoxy, (-C-C 4 ) alkylthio, (C ⁇ -C 4 ) haloalkylthio, mono dG alkylamino, di (C 1 -C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C 1 -C 4 ) alkyl] carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (C 1 -C) alkylamino-carbonyl, Di (CrC 4 ) al
  • heterocyclyl is generally or preferably defined as described above.
  • R 1 is also preferably hydrogen or in particular (C ⁇ -C6) alkyl, (C 2 - C 6) alkenyl, (C 2 -C 6) alkynyl, (C 1 -C 6) alkoxy or (C 1 -C 6) Alkylthio, each of the last 5 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, nitro, thiocyanato, (Cr C 4 ) alkoxy, (C ⁇ -C) haloalkoxy, (C 2 -C 4 ) alkenyloxy , (C 2 -C 4 ) haloalkenyloxy, (CC 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (CC 4 ) alkylsulfonyl, (CC 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkylsulf
  • Cycloalkyl which is unsubstituted or or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (-C-C 4 ) alkyl, (CrC 4 ) haloalkyl, (CrC 4 ) alkoxy , (CrC 4 ) haloalkoxy, (-C-C 4 ) alkylthio, (CC 4 ) haloalkylthio, mono (CrC 4 ) alkylamino and di (CrC 4 ) alkylamino is substituted, and phenyl and heterocyclyl, each of the latter two radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (C ⁇ -C 4 ) alkyl, (CC) hal
  • R 1 is more preferred
  • (CrC) alkyl which is unsubstituted or by one or more radicals from the group halogen, (C 1 -C 4 ) alkoxy, (CC 4 ) alkylthio, (C ⁇ -C 4 ) alkylsulfonyl and (C 3 -Cg) cycloalkyl, the is unsubstituted or substituted, and phenyl which is unsubstituted or by one or more radicals from the
  • Halogen group (-CC 4 ) alkyl and (CC 4 ) haloalkyl, (-C-C 4 ) alkoxy, (CC 4 ) haloalkoxy, (dC 4 ) alkylthio, amino, mono- and di [(CC 4 ) alkyl] amino, (C 1 -C 4 ) alkanoylamino, benzoylamino, nitro, cyano, [(C ⁇ -C) alkyl] carbonyl, formyl, carbamoyl, mono- and di - [(d- C) alkyl] aminocarbonyl and (C ⁇ -C 4 ) Alkylsulfonyl is substituted, and heterocyclyl with 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group N, O and S, the ring being unsubstituted or by one or more radicals from the group halogen, (-C-C) alkyl and oxo is substituted, is substitute
  • Phenyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (CrC 4 ) alkyl, (C ⁇ -C 4 ) haloalkyl, (C ⁇ -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (CC 4 ) alkylthio, (C 1 -C 4 ) haloalkylthio, mono (C ⁇ -C) alkylamino, di (CrC) alkylamino, (C 3 -C 9 ) cycloalkyl, [(CrC 4 ) alkyl] carbonyl, [(CrC) alkoxy] carbonyl, aminocarbonyl, mono (C ⁇ -C 4 ) alkylamino-carbonyl, di (C 1 -C 4 ) alkylamino-
  • R 1 is further preferred (CrC 4 ) alkyl, (-C-C 4 ) haloalkyl, benzyl or [(C 3 - C 6 ) cycloalkyl] - (C 1 -C 2 ) alkyl, in particular (C 1 -C 4 ) alkyl , (-CC 4 ) haloalkyl or [(C 3 - C 6 ) cycloalkyl] methyl, very particularly -CH 3 , -CH 2 F, -CHF 2 , -CF 3 , -CH 2 CI, -CHCI 2 , -CCI 3 , -CH 2 Br, -CHBr 2 , -CH 2 CH 3 , -CH 2 CH 2 F, -CF 2 CHF 2 , -CH 2 CH 2 CI, -CHFCH 3 , -CHFCH 2 CH 3 , - CH 2 Br, -CH (CH 3 ) 2) -CF (CH 3 )
  • R 1 is aryl which is unsubstituted or substituted and preferably contains 6 to 30 C atoms including substituents, or (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted and including substituents preferably Has 3 to 30 C atoms, or heterocyclyl which is substituted or unsubstituted and preferably contains 2 to 30 C atoms including substituents, or (CC 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) Alkynyl, each of the last 3 radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, nitro, thiocyanato, (-C-C 4 ) alkoxy, (CrC 4 ) haloalkoxy, (C 2 -C 4 ) Alkenyloxy, (C 2 -C) hal
  • R 1 is preferably also phenyl, which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (C 1 -C 4 ) alkyl, (-C-C 4 ) Haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (CC 4 ) alkylthio, (CC 4 ) haloalkylthio, mono (C ⁇ -C) alkylamino, di (C ⁇ -C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C ⁇ -C) alkyl] carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (C ⁇ -C) alkylamino-carbonyl, di (CrC 4 ) al
  • radicals R 1 , R 3 , R 4 , L °, A 1 , A 2 and (X) n and preferably in combination with preferred meanings of one or more of these radicals, the following meanings of R 2 are of particular interest:
  • R 2 is preferably (C 3 -Cg) cycloalkyl which is unsubstituted or substituted by one or more radicals from the group of the radicals A), B), C) and D), where group A) from the radicals halogen, hydroxy, Amino, nitro, formyl,
  • Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl are preferred as (C 3 -Cg) cycloalkyl radicals, in particular cyclopropyl, cyclobutyl or cyclopentyl.
  • Preferred (C 4 -C 9 ) cycloalkenyl radicals are 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl and 3-cyclopentenyl.
  • R 2 including substituents, preferably has up to 20 C atoms, in particular up to 15 C atoms, very particularly up to 10 C atoms.
  • R 2 is preferably (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted by one or more radicals from the group consisting of radicals A), B), C) and D), where
  • Group A consists of the radicals halogen, hydroxy, nitro, formyl, aminocarbonyl, cyano and thiocyanato,
  • Group C) consists of radicals according to group B), but each radical consists of one or more radicals from the group halogen, (CC 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (CC 4 ) alkylthio, (-C-C 4 ) haloalkylthio, mono (C ⁇ -C 4 ) alkylamino, di (C ⁇ -C 4 ) alkylamino, (C 3 -C 6 ) cycloalkyl, [(CC) alkyl] carbonyl, [(Ci -C 4 ) AI koxyjcarbonyl, aminocarbonyl, mono (-C-C 4 ) alkylamino-carbonyl, di (C ⁇ -C 4 ) alkylamino-carbonyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyciylami
  • C 3 -C 9 cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, thiocyanato, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, ( C 1 -C 4 ) alkoxy, (CC 4 ) haloalkoxy, (CrC 4 ) alkylthio, (C ⁇ -C 4 ) haloalkylthio, (C r C 4 ) alkylidene, mono (C ⁇ -C 4 ) alkylamino and di (CrC 4 ) alkylamino or heterocyclyl or phenyl, each of the latter two radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (CC
  • radicals R 1 , R 2 , R 4 , A 1 , A 2 , L ° and (X) n and preferably in combination with preferred meanings of one or more of these radicals, the following meanings of R 3 are of particular interest:
  • R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 in the above formulas are independent of one another
  • Hydrogen aryl which is unsubstituted or substituted and preferably has 6 to 30 C atoms including substituents, or (C 3 - C 9 ) cycloaikyl which is unsubstituted or substituted and preferably has 3 to 30 C atoms including substituents, or heterocyclyl , which is substituted or unsubstituted and including substituents preferably has 2 to 30 carbon atoms, or (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 residues unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, nitro, thiocyanato, (CrC 4 ) alkoxy, (C ⁇ -C) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) Haloalkenyloxy, (
  • R 12 , R 13 are each independent of one another
  • radicals R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 each independently represent hydrogen.
  • radicals R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 are each also independently of one another
  • Phenyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (dC 4 ) alkyl, (dC 4 ) haloalkyl, (dC 4 ) alkoxy, ( -C-C 4 ) haloalkoxy, (dd) alkylthio, (C ⁇ -C) haloalkylthio, mono (dC) alkylamino, di (C ⁇ -C 4 ) alkylamino, (C 3 -Cg) cycloalkyl, [(C ⁇ -C 4 ) alkyl ] carbonyl, [(-C-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (C ⁇ -C 4 ) alkylamino-carbonyl, di (C ⁇ -C) alkylamino-carbonyl, (C ⁇ -C
  • radicals R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 are each also independently of one another
  • (C 3 -C 9 ) cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (C 1 -C 4 ) alkyl, (dC 4 ) haloalkyl, (C 1 -C 4 ) Alkoxy, (dC 4 ) haloalkoxy, (dC 4 ) alkylthio, (CrC 4 ) haloalkylthio, mono (dC 4 ) alkylamino and di (dC 4 ) alkylamino is substituted and including substituents 3 to 30 C atoms, preferably 3 to 20 C -Atoms, in particular 3 to 15 carbon atoms.
  • radicals R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 are each also independently of one another
  • Heterocyclyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, Thiocyanato, (dC 4 ) alkyl, (CC 4 ) haloalkyl, (CC 4 ) alkoxy, (C 1 -C) haloalkoxy, (dC 4 ) alkylthio, (dC ⁇ haloalkylthio, mono (C ⁇ -C 4 ) alkylamino, di ( dC 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C -C 4 ) alkyl] carbonyl, [(C ⁇ -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (C ⁇ -C 4 ) alkylamino-carbonyl, di (-C-C) alkylamino-carbonyl, (-
  • R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 are each, independently of one another, preferably also (CrC 6 ) alkyl, (C 2 -C 6 ) Alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, nitro, thiocyanato, (C 1 -C 4 ) alkoxy, (d- C 4 ) Haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (CC 4 ) alkylthio, (CC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulf
  • R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 are each independently preferred (-C-C 4 ) alkyl which is unsubstituted or by one or more radicals from the group consisting of halogen, (dC 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (dC 4 ) alkylsulfonyl, (C 3 - Cg) cycloalkyl which is unsubstituted or substituted, and phenyl which is unsubstituted or substituted by one or more radicals from the group halogen, (-CC 4 ) alkyl and (dC 4 ) haloalkyl, (dC 4 ) alkoxy, (C 1 -C) haloalkoxy, (-C-C 4 ) alkylthio, amino, mono- and Di [(-C-C 4 )
  • R 12 , R 13 are each independently, preferably also phenyl, which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (CrC 4 ) alkyl, (C ⁇ -C 4 ) haloalkyl, (dC 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (dC 4 ) alkylthio, (C ⁇ -C 4 ) haloalkylthio, mono (dC 4 ) alkylamino, di (dC) alkylamino, (C 3 -C 9 ) cycloalkyl, [(CrC 4 ) alkyl] carbonyl, [(-C-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (C ⁇ -C 4 ) alkylamino-carbonyl, di (C
  • R 12 , R 3 are each independently of one another preferably also (C 3 -C 9 ) cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (-C-C) alkyl, (-C.
  • R 12 , R 13 are each, independently of one another, preferably also heterocyclyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (C 1 -C 8) alkyl, ( dC 4 ) haloalkyl, (dC 4 ) alkoxy, (C ⁇ -C 4 ) haloalkoxy, (CC 4 ) alkylthio, (C ⁇ -C) haloalkylthio, mono (dC 4 ) alkylamino, di (C ⁇ -C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(-C-C 4 ) alkyl] carbonyl, [(dC 4 ) alkoxy] carbonyl, aminocarbonyl, mono (CrC 4 ) alkylamino-carbonyl, di
  • R 12 , R 13 are each, independently of one another, preferably also (-C 6 ) alkyl, (C 2 -Ce) alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 residues being unsubstituted or by one or more residues the group halogen, hydroxy, cyano, nitro, thiocyanato, (C ⁇ -C 4 ) alkoxy, (C ⁇ -C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (CC 4 ) Alkylthio, (C 1 -C 4 ) alkylsulfinyl, (d- C 4 ) alkylsulfonyl, (C ⁇ -C) haloalkylsulfinyl, (C ⁇ -C) haloalkylsulfonyl, (C 3 -C 6 )
  • R 12 , R 13 are each independently preferred (-CC 4 ) alkyl which is unsubstituted or by one or more radicals from the group halogen, (dC 4 ) alkoxy, (dC 4 ) alkylthio, (dC 4 ) alkylsulfonyl, ( C 3 -C 9 ) Cycloalkyl, which is unsubstituted or substituted, and phenyl, which is unsubstituted or by one or more radicals from the group halogen, (-C-C) alkyl and (dC) haloalkyl, (dC 4 ) alkoxy, (CC ) Haloalkoxy, (CC 4 ) alkylthio, amino, mono- and di [(CC 4 ) alkyl] amino, (C -C 4 ) alkanoylamino, benzoylamino, nitro, cyano, [(Ci-C 4 ) alkyl] carbonyl, formyl
  • radicals R 1 , R 2 , R 3 , L °, A 1 , A 2 and (X) n and preferably in combination with preferred meanings of one or more of these radicals, the following meanings of R 4 are of particular interest:
  • R 4 means, for example, a radical of the formula -B 1 -D 1 , where B 1 and D 1 are preferably as defined below.
  • R 4 is preferably hydrogen, (C 1 -C) alkyl, phenyl or (C 3 -C 6 ) cycloalkyl, each of the 3 last-mentioned radicals being unsubstituted or by one or more radicals from the group consisting of halogen, hydroxy, amino, nitro, formyl , Carboxy, sulfonyl, cyano, thiocyanato, (C ⁇ -C 4 ) alkoxy, (C ⁇ -C 4 ) haloalkoxy, (dC 4 ) alkylthio, (C ⁇ -C 4 ) haloalkylthio, mono (dC 4 ) alkylamino, di (dC) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C 1 -C 4 ) alkyl] carbonyl, [(C ⁇ -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (dC 4 )
  • L ° is a direct bond or Oxygen.
  • a 1 means, for example, straight-chain alkylene with 1 to 5 C atoms or straight-chain alkenylene or alkynylene each with 2 to 5 C atoms, each of the three last-mentioned diradicals being unsubstituted or by one or more radicals from the group halogen, nitro, cyano, thiocyanato and a radical of the formula -B 2 -D 2 is substituted, in which B 2 is a direct bond or a divalent group of the formulas -O-, -SO 2 -, -CO-, -O-CO-, -NR ° -, -NR ° -CO-, -CO-NR 0 -, -O-CO-NR 0 - or -NR °
  • R ° independently of one another are each hydrogen, (dC 4 ) alkyl, phenyl, phenyl- (dC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (C 1 -C 4 ) alkyl, where each of the last 5 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (C ⁇ -C) alkoxy, (C ⁇ -C 4 ) haloalkoxy, ( CrC 4 ) alkylthio, (dC 4 ) haloalkylthio, mono (CC) alkylamino, di (C 1 -C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C ⁇ -C 4 ) alkyl
  • a 1 is preferably a radical of the formula
  • a 1 is particularly preferably a radical of the formula -CH 2 CH 2 - or -CH 2 CH 2 CH 2 - which is unsubstituted or by one or two radicals of the formula hydroxyl, (-CC 4 ) alkyl or (-CC) Alkoxy is substituted.
  • a 2 is preferably a direct bond or a group of the formula -CH 2 -, -CH 2 CH 2 -,
  • Halogen, nitro, cyano, thiocyanato and radicals of the formula -B 3 -D 3 is substituted, or a divalent radical of the formula V 1 , V 2 , V 3 , V 4 or V 5 ,
  • W * is in each case O, S or a group of the formula N (B 5 -D 5 ) and
  • B 3 , B 4 , B 5 , D 3 , D 4 and D 5 are as defined below,
  • a 2 is particularly preferably a direct bond or a group of the formula -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH, -CH2-O-CH 2 -, -CH 2 -O-CH 2 -CH 2 -, -CH 2 -CH 2 -O-CH 2 -, -CH -S-CH 2 -, -CH 2 -S-CH 2 -CH 2 -, -CH 2 -CH 2 -S-CH 2 -, -CH 2 -NH-CH 2 -, -CH 2 -NH-CH 2 -CH 2 -, -CH 2 -CH 2 -NH-CH 2 -, - CH 2 -N (CH 3 ) -CH 2 -, -CH 2 -N (CH 3 ) -CH 2 -CH 2 - or -CH 2 -CH 2 -CH 2 -N (CH 3 )
  • B 2 , B 3 and B 4 are more preferably, independently of one another, a direct bond or a divalent group of the formulas -O-, -S (O) p -, -CO-,
  • D 1 , D 2 , D 3 , D 4 and D 5 preferably independently of one another are hydrogen, (dd alkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 - C ⁇ JCycloalkyKd -C ⁇ Jalkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (dC) alkoxy, (C ⁇ -C 4 ) haloalkoxy, (dC) alkylthio, (dC 4 ) haloalkylthio, mono (C ⁇ -C 4 ) alkylamino, di (dC 4 ) alkylamino, (C 3
  • D 1 , D 2 , D 3 , D 4 and D 5 are furthermore preferably (C 1 -C 4 ) alkyl, phenyl, phenyl- (dC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 - C 6 ) Cycloalkyl- (-C-C 4 ) alkyl, each of the 5 last-mentioned radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, formyl, (dC) alkoxy, (-C-C 4 ) haloalkoxy, (CC 4 ) alkylthio, mono (C ⁇ -C 4 ) alkylamino, di (CC 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(dC 4 ) alkyl ] carbonyl, [(C -C 4 ) alkoxy] carbonyl, aminocarbonyl,
  • radicals R 1 to R 4 , L °, A 1 and A 2 and preferably in combination with preferred meanings of one or more of these radicals the following meanings of (X) n are of particular interest:
  • (X) n denotes n substituents X, the radicals X preferably each independently of the other halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, aminocarbonyl or (C 1 -C 4 ) alkyl, (CrC 4 ) alkoxy, (C 1 C -C 4 ) alkylthio, mono (dC 4 ) alkylamino, di (CC 4 ) alkylamino, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, [(dC 4 ) alkyl] carbonyl, [(dC 4 ) alkoxy] carbonyl, mono (-C-C 4 ) alkylamino-carbonyl, di (dC 4 ) alkylamino-carbonyl, N- (CrC 6 ) alkanoyl-amino or N- (C ⁇ -C 4 ) alkan
  • n is preferably 0, 1, 2 or 3, in particular 0, 1 or 2.
  • (X) n further preferably denotes n substituents X, the radicals X each independently of one another halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, (C 1 -C 4 ) alkyl, cyano- (CrC) alkyl, ( -C-C) alkoxy, (-C-C 4 ) alkylamino, di - [(dC) alkyl] -amino, halo (C ⁇ -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl ) (C 1 - C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo (dC 4 ) alkoxy- (CC 4 ) alkyl, (C ⁇ -C 4 ) alkylthio, halo- (dC 4 ) alkylthio, (C 2 -C 6 ) Alkenyl, hal
  • radicals X together represent a fused-on cycle with 4 to 6 ring atoms, which is carbocyclic or contains hetero ring atoms from the group O, S and N and which is unsubstituted or by one or more radicals from the group halogen, (C ⁇ - C) alkyl and oxo is substituted.
  • (X) n particularly preferably denotes n substituents X, where the radicals X are each, independently of one another, halogen, OH, N0 2 , CN, SCN, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy, (dC 4 ) alkylcarbonyl or (-CC 4 ) alkyloxycarbonyl, the latter four radicals being unsubstituted or substituted by halogen or (-C-C) alkoxy, and very particularly preferably denotes n substituents X, where the radicals X are each independently halogen, hydroxy, (dC 4 ) alkyl or (-C-C 4 ) alkoxy mean.
  • Heterocyclyl in the radicals mentioned above or further below, independently of one another, preferably denotes a heterocyclic radical having 3 to 7 ring atoms and 1 to 3 heteroatoms from the group N, O and S, preferably a heteroaromatic radical from the group pyridyl, pyrimidinyl, pyridazinyl, pyrazinyi, Triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl, imidazolyl and triazolyl or a partially or completely hydrogenated heterocyl radical from the group oxiranyl, oxetanyl, oxolanyl ( tetrahydrofuryl, piperyl, piperyl, piperyl, piperyl Dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidiny
  • Heterocyclyl particularly preferably denotes a heterocyclic radical with 3 to 6 ring atoms and one (1) heteroatom from the group N, O and S, in particular a heteroaromatic radical with 5 or 6 ring atoms or a saturated or partially unsaturated heterocyclic (non-heteroaromatic) radical with 3 up to 6 ring atoms.
  • heterocyclyl preferably denotes a heterocyclic radical with 5 or 6
  • Ring atoms and with 2 or 3 heteroatoms from the group N, O and S in particular pyrimidinyl, pyridazinyl, pyrazinyi, triazinyl, thiazolyl, thiadiazolyl,
  • the composite group -A 2 -R 2 is preferably cyclopropyl (hereinafter also “c-Pr”), CH 2 -c-Pr, - (CH 2 ) 2 -c-Pr, cyclobutyl (hereinafter also “c-Bu”) , CH 2 -c-Bu; (CH 2 ) 2 - c-Bu, oxiranyl, oxiranyl-methyl or 2- (oxiranyl) -eth-1-yl.
  • c-Pr cyclopropyl
  • CH 2 -c-Pr CH 2 -c-Pr
  • - (CH 2 ) 2 -c-Pr cyclobutyl
  • CH 2 -c-Bu CH 2 -c-Bu
  • oxiranyl oxiranyl
  • the present invention also relates to processes for the preparation of compounds of the formula (I) and their salts,
  • a 1 , A 2 , L °, R 1 , R 2 , R 3 , R 4 , X and n are as defined above, characterized in that
  • a 1 , A 2 , L °, L 1 , R 1 , R 2 , R 4 , X and n are as defined in formula (I), with a compound of formula (III),
  • U 1 and U 3 are as defined in formula (I) and R 18 and R 19 independently of one another each represent optionally substituted alkyl having up to 12 carbon atoms, preferably (C 1 -C 4 ) alkyl or are joined together to form an alkylene group with 2 to 4 carbon atoms mean, or
  • a 1 , A 2 , L °, L 1 , R 1 , R 2 , R 4 , G 1 , X and n are as defined in formula (I), with a compound of
  • a 1 , A 2 , L °, L 1 , R 1 , R 2 , R 4 , U 1 , X and n are as defined in formula (I) and R 6 and R 7 are as defined above, with one Compound of formula (VII) or their acid adducts,
  • substituted aminotriazines of the formula (II) used in the process according to the invention, variant a) for the preparation of compounds of the formula (I) are known and / or can be prepared by processes known per se (cf. WO-A-9965882).
  • Variant a) of the process according to the invention for the preparation of compounds of the general formula (I) is carried out, if appropriate, using a diluent.
  • Inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyroni
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are used, for example, in equimolar amounts.
  • one of the components in a more or less large excess, e.g. B. if the component used in the deficit should react quickly to reduce side reactions.
  • the reaction is carried out, for example, in a suitable diluent in the presence of a reaction auxiliary, the reaction mixture generally being mixed, for example stirred, at the required temperature for several hours.
  • the work-up can be carried out using customary methods (cf. also the preparation examples).
  • substituted aminotriazines of the formula (IV) used in the process according to the invention, variant b) for the preparation of compounds of the formula (I) are known and / or can be prepared by processes known per se (cf. WO-A-9965882).
  • the compounds of formula (V) are known, for example, from J. Org. Chem. 30, pp. 2531-2533 (1965).
  • the process according to the invention for the preparation of compounds of the general formula (I) according to variant b) is optionally carried out using a diluent.
  • Inert organic solvents are particularly suitable as diluents.
  • aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as NN-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl methylformamide,
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • inventive method according to variant b) is carried out in a simple manner, for example under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - preferably between 0.1 bar and 10 bar.
  • the starting materials can be used in equimolar amounts. However, it is also possible to use one of the components in a more or less large excess.
  • the reaction is preferably carried out in a suitable diluent in the presence of a reaction auxiliary. The reaction usually runs completely within several hours with stirring at the required temperature.
  • the work-up can be carried out by customary methods (cf. the production examples).
  • Compounds of the formula (VI) are used to prepare the compounds (I) according to variant c).
  • the compounds of formula (VII) are known or can be prepared by known methods.
  • the method according to variant c) according to the invention is optionally carried out using a diluent.
  • diluents include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrii; Amides such as N, N-dimethylformamide, N
  • reaction conditions such as ranges for reaction temperatures, pressure conditions, quantitative ratios etc. are comparable to those in variants a) and b).
  • the method according to variant d) according to the invention is optionally carried out using a diluent.
  • Inert organic solvents are particularly suitable as diluents.
  • aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl
  • reaction conditions such as ranges for reaction temperatures, pressure conditions, quantitative ratios etc. are comparable to those in variants a) and b) and c).
  • the water released during the reaction can be e.g. B. by acetrope distillation, water-binding salts or molecular sieves.
  • the respective starting compounds of the formulas (II) to (VIII) are known or can be prepared by the methods indicated above or by methods known analogously.
  • the following acids are suitable for the preparation of the acid addition salts of the compounds of the formula (I): hydrohalic acids such as hydrochloric acid or hydrobromic acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- or bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid Salicylic acid, sorbic acid or lactic acid, and sulfonic acids such as p-toluenesulfonic acid or 1, 5-naphthalenedisulfonic acid.
  • the acid addition compounds of the formula (I) can be prepared in a simple manner by the customary salt formation methods, for example by dissolving a compound of the formula (I) in a suitable organic solvent such as methanol, acetone, methylene chloride or gasoline and adding the acid at temperatures from 0 to 100 ° C are obtained and isolated in a known manner, for example by filtering, and optionally cleaned by washing with an inert organic solvent.
  • a suitable organic solvent such as methanol, acetone, methylene chloride or gasoline
  • the base addition salts of the compounds of formula (I) are preferably in inert polar solvents such as e.g. Water, methanol or acetone at temperatures from 0 to 100 C.
  • Suitable bases for the preparation of the salts according to the invention are, for example, alkali carbonates, such as potassium carbonate, alkali and alkaline earth metal hydroxides, e.g. NaOH or KOH, alkali and alkaline earth hydrides, e.g. NaH, alkali and alkaline alcoholates, e.g. Sodium methoxide, potassium tert-butoxide, or ammonia or ethanolamine.
  • Quaternary ammonium salts can e.g. by salting or condensation with quaternary ammonium salts of the formula
  • inert solvents mean in each case solvents which are inert under the respective reaction conditions but do not have to be inert under any reaction conditions.
  • a collection of compounds (I) which can be synthesized according to the above-mentioned methods can additionally be produced in a parallelized manner, which can be done in a manual, partially automated or fully automated manner. It is possible to automate the implementation of the reaction, the processing or the cleaning of the products or intermediate stages. Overall, this is understood to mean a procedure as described, for example, by SH DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis", Volume 1, Escom Verlag, 1997, pages 69 to 77.
  • a number of commercially available devices can be used for parallelized reaction execution and processing, for example those offered by Stern Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England or H + P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleissheim, Germany become.
  • Chromatography apparatus for example from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA, is available for the parallelized purification of compounds (I) or of intermediate products obtained during production.
  • the equipment listed enables a modular procedure in which the individual work steps are automated, but manual operations must be carried out between the work steps. This can be avoided by using partially or fully integrated automation systems in which the respective automation modules are operated by robots, for example. Automation systems of this type can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA.
  • compounds (I) can be prepared completely or partially by methods supported by solid phases.
  • solid phases For this purpose, individual intermediate stages or all intermediate stages of the synthesis or a synthesis adapted for the corresponding procedure are bound to a synthetic resin.
  • Solid phase supported synthesis methods are in the specialist literature is adequately described, e.g. For example: Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998.
  • the preparation according to the processes described here provides compounds (I) in the form of substance collections or libraries.
  • the present invention therefore also relates to libraries of the compounds (I) which contain at least two compounds (I) and their precursors.
  • the compounds of the formula (I) according to the invention and their salts, hereinafter referred to collectively as (compounds) of the formula (I) according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants.
  • Perennial weeds that are difficult to control and that sprout from rhizomes, rhizomes or other permanent organs are also well captured by the active ingredients. It does not matter whether the substances are applied by pre-sowing, pre-emergence or post-emergence.
  • weed species for example, Agrostis, Alopecurus, Apera, Avena, Brachicaria, Bromus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Festuca, Fimbristylis, Ischaemum, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Sagittaria, Scirpus, Setaria, Sphenoclea, as well as Cyperus species mainly from the annual group and on the part of the perennial species Agroponata, Cynodyron, Cyn as well as sorghum and perennial cyperus species.
  • herbicidal activity in dicotyledon weeds such as Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rioaes, Sotala, Sotala, Sotala Solanum, Sonchus, Taraxacum, Trifolium, Urtica and Xanthium.
  • herbicidal activity in dicotyledon weeds such as Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rioaes, Sotala, Sotala, Sotala Solanum, Sonchu
  • the compounds according to the invention are applied to the surface of the earth before germination, either the weed seedlings emerge completely or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.
  • the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops such as, for example, wheat, barley, rye, triticale, rice, corn, sugar beet, cotton and soybean are only insignificantly or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops, including ornamental crops.
  • the substances according to the invention have excellent growth-regulating properties in crop plants. They intervene in the plant's metabolism in a regulating manner and can thus be used to influence plant constituents in a targeted manner and to facilitate harvesting, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesired vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as this can reduce or completely prevent storage.
  • the active compounds can also be used to control harmful plants in crops of known or still to be developed genetically modified plants.
  • the transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogen pathogens such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. B. the crop in terms of quantity, quality, storability, composition and special ingredients.
  • transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
  • B. of cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • the compounds of the formula (I) can preferably be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made resistant to genetic engineering.
  • new plants which have modified properties in comparison to previously occurring plants are, for example, classic breeding methods and the generation of mutants.
  • new plants with modified properties can be produced using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624).
  • genetic engineering changes in crop plants have been described in order to modify the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827,
  • Glufosinate see e.g. EP-A-0242236, EP-A-242246) or glyphosate
  • Bacillus thuringiensis toxins (Bt toxins) which the
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of the above standard procedures such. B. base exchanges, partial sequences removed or natural or synthetic sequences added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments.
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically cleaves transcripts of the gene product mentioned above.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
  • the synthesized protein When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a particular compartment, z. B. the coding region can be linked to DNA sequences that localize in guarantee a certain compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1: 95-106 (1991).
  • the transgenic plant cells can be regenerated into whole plants using known techniques.
  • the transgenic plants can in principle be plants of any plant species, i.e. both monocot and dicot plants.
  • the compounds (I) according to the invention can preferably be used in transgenic crops which are resistant to herbicides from the group of the sulfonylureas, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active compounds.
  • the active compounds according to the invention are used in transgenic crops, in addition to the effects on harmful plants which can be observed in other crops, there are often effects which are specific to the application in the respective transgenic culture, for example a changed or specially expanded weed spectrum which can be controlled changed Application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing the growth and yield of the transgenic crop plants.
  • the invention therefore also relates to the use of the compounds (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the use according to the invention for controlling harmful plants or for regulating the growth of plants also includes the case in which the active compound of the formula (I) or its salt is obtained from a precursor substance only after application to the plant, in the plant or in the soil ("Prodrug ”) is formed.
  • the compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also relates to herbicidal and plant growth-regulating compositions which comprise compounds of the formula (I).
  • the compounds of formula (I) can be formulated in different ways, depending on which biological and / or chemical-physical parameters are specified. Possible formulation options are, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), pickling agents, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and Adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powder
  • EC emulsifiable concentrates
  • EW emulsions
  • combinations with other pesticidally active substances e.g. Manufacture insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a finished formulation or as a tank mix.
  • pesticidally active substances e.g. Manufacture insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or an inert substance, but also ionic and / or nonionic surfactants (wetting agents, dispersing agents), e.g.
  • the herbicidal active ingredients are finely ground, for example in conventional apparatus such as hammer mills, fan mills and air jet mills, and mixed at the same time or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents.
  • ionic and / or nonionic surfactants emulsifiers
  • emulsifiers may be used, for example: calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan fatty acid such as Polyoxethylensorbitanester.
  • calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants, such as those e.g. already listed above for the other types of formulation.
  • Emulsions e.g. Oil-in-water emulsions (EW) can be used, for example, with stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as those e.g. already listed above for the other formulation types.
  • EW Oil-in-water emulsions
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylic acid or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material.
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
  • Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active ingredient of the formula (I).
  • the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components.
  • the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight.
  • Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating aids, fillers, etc. are used.
  • the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity.
  • the compounds of formula (I) or their salts can be used as such or in the form of their preparations (formulations) with other pesticidal substances, such as B. insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators can be used in combination, for. B. as a finished formulation or as a tank mix.
  • active substances As a combination partner for the active substances according to the invention in mixture formulations or in the tank mix, there are, for example, known active substances which are based on an inhibition of, for example, acetoiactate synthase, acetyl-coenzyme A carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen Oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase are used.
  • active substances which are based on an inhibition of, for example, acetoiactate synthase, acetyl-coenzyme A carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen Oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase are used.
  • herbicides known from the literature which can be combined with the compounds of the formula (I) are the following active ingredients (note: the compounds are either with the "common name” according to the international organization for standardization (ISO) or with the chemical name , possibly together with a usual code number): acetochlor; acifluorfen (-sodium); aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and methyl acetate; alachlor; alloxydim (-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; amitrol; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azafenidin, azimsulfurone (DPX-A89
  • the selective control of harmful plants in crops of useful and ornamental plants is of particular interest.
  • the compounds (I) according to the invention already have very good to sufficient selectivity in many crops, phytotoxicity can occur on the crop plants in principle in some crops and especially in the case of mixtures with other herbicides which are less selective.
  • combinations of compounds (I) according to the invention which contain the compounds (I) or their combinations with other herbicides or pesticides and safeners are of particular interest.
  • the safeners which are used in an antidotically effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, eg. B.
  • cereals wheat, barley, rye, corn, rice, millet
  • sugar beet sugar cane
  • rapeseed cotton and soy
  • cotton and soy preferably cereals.
  • safeners for the compounds (I) and their combinations with other pesticides are suitable, for example, as safeners for the compounds (I) and their combinations with other pesticides:
  • dichlorophenylpyrazole carboxylic acid preferably compounds such as 1 - (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylic acid ethyl ester (S1 -2), 1- ( 2,4-dichlorophenyl) -5-isopropyl-pyrazole-3-carboxylic acid ethyl ester (S1-3), 1- (2,4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (S1 -4), 1 - (2,4-dichlorophenyl) -5-phenyl-pyrazole-3-carboxylic acid ethyl ester (S1 -5) and related compounds as described in EP-A-333 131 and EP-A-269 806 are described.
  • EP-A-191 736 or EP-A-0 492 366 Compounds of the type of (5-chloro-8-quinolinoxy) malonic acid, preferably compounds such as (5-chloro-8-quinolinoxy) malonic acid diethyl ester, (5-chloro-8-quinolinoxy) malonic acid diallyl ester, (5- Chloro-8-quinolinoxy) -malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198.
  • active substances of the phenoxyacetic or propionic acid derivative or aromatic carboxylic acid type e.g.
  • Safeners known for pretilachlor in sown rice are i) active substances of the dichloroacetamide type, often used as pre-emergence safeners
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide from the
  • Cyanomethoxyimino (phenyl) acetonitrile which is known as a seed dressing safener for millet against damage to metolachlor, I) active substances of the thiazole carboxylic acid ester type, which are known as seed dressings, such as, for. B.
  • Seed dressings are known, such as. B.
  • Naphthalenedicarboxylic anhydride which acts as a seed dressing safener against corn
  • n active substances of the chromanacetic acid derivative type, such as. B.
  • the weight ratio of herbicide (mixture) to safener generally depends on the amount of herbicide applied and the effectiveness of the particular safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds (I) or their mixtures with further herbicides / pesticides and can be provided and used as a finished formulation or tank mixture with the herbicides.
  • the herbicide or herbicide safener formulations present in commercial form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, using water. Preparations in the form of dust, ground granules or scattering granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate of the compounds of formula (I) varies with the external conditions, such as temperature, humidity, the type of herbicide used, and others. It can vary within wide limits, for example between 0.001 and 10.0 kg / ha or more of active substance, but is preferably between 0.005 and 5 kg / ha, in particular 0.01 and 3 kg / ha.
  • Ph phenyl
  • Ph phenyl
  • a dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as an inert substance and comminuting in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyitauric acid sodium as wetting and dispersing agent and grind in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight.
  • Parts of paraffinic mineral oil (boiling range e.g. approx. 255 to above 277 ° C) and ground in a friction ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
  • a water-dispersible granulate is also obtained by 25 parts by weight of a compound of the formula (I),
  • Homogenize 50 "water on a colloid mill and pre-crush it, then grind it on a bead mill and atomize and dry the suspension thus obtained in a spray tower using a single-component nozzle.
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants are placed in sandy loam in plastic pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders or emulsion concentrates are then applied as an aqueous suspension or emulsion with a water application rate of the equivalent of 600 to 800 l / ha in different dosages to the surface of the covering earth.
  • the pots are placed in the greenhouse and kept under good growth conditions for the weeds. After the test plants have emerged, the optical damage to the plants or the emergence damage is assessed after a test period of 3 to 4 weeks in comparison to untreated controls.
  • the compounds according to the invention show a very good pre-emergence activity against a broad spectrum of grasses and weeds.
  • harmful plants such as Stellaria media, Lolium multiforum, Amaranthus retroflexus, Sinapis alba, Avena sativa and Setaria viridis are used by compounds according to the invention (see examples A1 to A3 and connections 2-1, 2-35, 2-36, 2-45, 2-55, 2-56, 3-1, 3-14, 3-25, 3-37, 3- 38, 3-40, 3-41, 3-43, 3-44, 3-46, 3-47, 3-55, 3-56, 3-58, 3-59, 3-67, 3-68, 3-70, 3-71, 3-74, 3-85, 3-86, 3-124, 5-1, 5-40, 8-2, 8-11, 8-20, 8-21, 8- 27 and 8-37 from Tables 1 to 12) very well combated in the pre-emergence process.
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds are placed in sandy loam soil in plastic pots, covered with soil and grown in the greenhouse under good growth conditions. Three weeks after sowing, the test plants are treated at the three-leaf stage.
  • the compounds according to the invention formulated as wettable powder or as emulsion concentrates are sprayed onto the green parts of the plant in various dosages with a water application rate of the equivalent of 600 to 800 l / ha. After the test plants have stood in the greenhouse for about 3 to 4 weeks under optimal growth conditions, the effect of the preparations is assessed visually in comparison with untreated controls.
  • the agents according to the invention also have good herbicidal activity against a broad spectrum of economically important grasses and weeds, for example against harmful plants such as Sinapis alba, Echinochloa crus-galli, Lolium multiflorum, Stellaria media, Cyperus iria, Amaranthus retroflexus, Setaria viridis and Avena sativa of the compounds according to the invention (see examples A1 to A3 and compounds 2-1, 2-35, 2-36, 2-45, 2-55, 2-56, 3-1, 3-14, 3-25, 3 -37, 3-38, 3-40, 3-41, 3-43, 3-44, 3-46, 3-47, 3-55, 3-56, 3-58, 3-59, 3-67 , 3-68, 3-70, 3-71, 3-74, 3-85, 3-86, 3-124, 5-1, 5-40, 8-2, 8-11, 8-20, 8 -21, 8-27 and 8-37 from Tables 1 to 12) in the post-emergence process with an application rate of 1 kg and less active substance per
  • Transplanted and sown rice as well as typical rice weeds and grass weeds are grown in the greenhouse up to the three-leaf stage (Echinochloa crus-galli 1,5-leaf) Paddy rice conditions (water accumulation height: 2 - 3 cm) grown in closed plastic pots.
  • the treatment with the compounds according to the invention is then carried out.
  • the formulated active ingredients are suspended in water, dissolved or emulsified and applied by pouring application into the backwater of the test plants in different dosages. After the treatment has been carried out in this way, the test plants are placed in the greenhouse under optimal growth conditions and are kept this way throughout the test period.
  • the compounds according to the invention show very good herbicidal activity against harmful plants, such as Cyperus monti, Echinochloa crus-galli and Sagittaria pygmaea.
  • Some substances also protect Gramineae crops such as barley, wheat, rye, sorghum, corn or rice.
  • the Compounds of the formula (I) show a high selectivity in some cases and are therefore suitable for combating undesired plant growth in agricultural crops.

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Abstract

The invention relates to compounds of formula (I) and to the salts thereof, wherein R<1> to R<4>, A<1>, A<2>, L<0>, X and n are defined as in claim 1. The inventive compounds are useful as herbicides and plant growth regulators and are produced by a method according to claim 6.

Description

Beschreibung description
SUBSTITUIERTE 2-AMIN0-1, 3, 5-TRIAZINE UND IHRE VERWENDUNG ALS HERBIZIDE UNDSUBSTITUTED 2-AMIN0-1, 3, 5-TRIAZINE AND THEIR USE AS HERBICIDES AND
PFLANZENWACHSTUMSREGULATORENPLANT GROWTH REGULATORS
Die Erfindung betrifft das technische Gebiet der Pflanzenschutzmittel, wie Herbizide und Pflanzenwachtumsregulatoren, insbesondere der Herbizide zur selektiven Bekämpfung von Schadpflanzen in Nutzpflanzenkulturen.The invention relates to the technical field of crop protection agents, such as herbicides and plant growth regulators, in particular herbicides for the selective control of harmful plants in crops of useful plants.
Es ist bekannt, daß in 6-Stellung substituierte 2-Amino-4-(N-Phenylalkyl-amino)- 1 ,3,5-triazine, die noch weiter substituiert sein können, herbizide und pflanzenwachstumsregulierende Eigenschaften besitzen; vgl. WO97/08156 und dort zitierte Literatur, WO 99/37627 und dort zitierte Literatur WO98/15537und dort zitierte Literatur; vgl. teilweise auch WO 97/00254 und dort zitierte Literatur.It is known that 2-amino-4- (N-phenylalkylamino) -1,3,5-triazines which are substituted in the 6-position and which may be further substituted have herbicidal and plant growth-regulating properties; see. WO97 / 08156 and literature cited there, WO 99/37627 and literature cited there WO98 / 15537 and literature cited there; see. partly also WO 97/00254 and literature cited there.
Die bekannten Wirkstoffe weisen bei ihrer Anwendung teilweise Nachteile auf, sei es unzureichende herbizide Wirkung gegen Schadpflanzen, zu geringes Spektrum der Schad pflanzen, das mit einem Wirkstoff bekämpft werden kann, oder zu geringe Selektivität in Nutzpflanzenkulturen. Andere Wirkstoffe lassen sich wegen schwer zugänglicher Vorprodukte und Reagenzien im industriellen Maßstab nicht wirtschaftlich herstellen oder besitzen nur unzureichende chemische Stabilitäten.The known active ingredients sometimes have disadvantages when used, whether it is inadequate herbicidal activity against harmful plants, too small a range of harmful plants which can be combated with an active ingredient, or insufficient selectivity in crops of useful plants. Other active ingredients cannot be produced economically on an industrial scale because of the difficult to access precursors and reagents, or they have insufficient chemical stability.
Aufgabe der Erfindung ist es, alternative Wirkstoffe vom Typ der 2-Amino-1 ,3,5- Triazine bereitzustellen, die gegebenenfalls mit Vorteilen als Herbizide oder Pflanzenwachstumsregulatoren eingesetzt werden können.The object of the invention is to provide alternative active compounds of the 2-amino-1,3,5-triazine type, which can optionally be used with advantages as herbicides or plant growth regulators.
Gegenstand der vorliegenden Erfindung sind Verbindungen der Formel (I) und deren Salze, The present invention relates to compounds of the formula (I) and their salts,
worinwherein
R1 Aryl, Aryloxy, Arylthio, Arylamino, N-Aryl-N-(Cι-C4)alkyl-amino, (C3- C9)Cycloalkyl, (C3-C9)Cycloalkyloxy, (C3-C9)Cycloalkylthio, (C3- Cg)Cycloalkylamino, N-(C3-C9)Cycloalkyl-N-(CrC4)alkyl-amino, Di-[(C3- C9)cycloalkyl]-amino, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio, Heterocyciylamino oder N-Heterocyclyl-N-(CrC4)alkyl-amino, wobei jeder der letztgenannten 16 Reste unsubstituiert oder substituiert ist, vorzugsweise unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (C C6)Alkyl, (C C6)Haloalkyl, (C2-C6)Alkenyl, (C2-C6)Haloalkenyl, (C2-C6)Alkinyl, (C2-C6)Haloalkinyl, (Cι-C6)Alkoxy, (Cι-C6)Haloalkoxy, (C2-C6)Alkenyloxy, (C2-C6)Haloalkenyloxy, (C2-C6)Alkinyloxy, (C2-C6)Haloalkinyoxy, (C C6)Alkylthio, (C1-C6)Haloalkylthio, Mono(Cι-C6)alkylamino, Di(CrC6)alkylamino, (C3-C9)Cycloalkyl, (C5-C9)Cycloalkenyl, [(CrC5)Alkyl]carbonyl, [(CrC6)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C6)alkylamino-carbonyi, Di(Cι.-C6)alkylamino- carbonyl, (Cι-C6)Alkylsulfonyl und (C C6)Haloalkylsulfonyl substituiert ist und inklusive Substituenten vorzugsweise bis zu 30 C-Atome aufweist, oderR 1 aryl, aryloxy, arylthio, arylamino, N-aryl-N- (-C-C 4 ) alkyl-amino, (C 3 - C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyloxy, (C 3 -C 9 ) Cycloalkylthio, (C 3 - Cg) cycloalkylamino, N- (C 3 -C 9 ) cycloalkyl-N- (CrC 4 ) alkylamino, di - [(C 3 - C 9 ) cycloalkyl] amino, heterocyclyl, heterocyclyloxy , Heterocyclylthio, Heterocyciylamino or N-heterocyclyl-N- (CrC 4 ) alkyl-amino, where each of the latter 16 residues is unsubstituted or substituted, preferably unsubstituted or by one or more residues from the group halogen, hydroxy, amino, nitro, formyl , Carboxy, sulfo, cyano, thiocyanato, (CC 6 ) alkyl, (CC 6 ) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkynyl, (Cι-C 6 ) alkoxy, (Cι-C 6 ) haloalkoxy, (C 2 -C 6 ) alkenyloxy, (C 2 -C 6 ) haloalkenyloxy, (C 2 -C 6 ) alkynyloxy, (C 2 -C 6 ) haloalkinyoxy, (CC 6 ) alkylthio, (C 1 -C 6 ) haloalkylthio, mono (Cι-C 6 ) alkylamino, di (CrC 6 ) alkylamino, (C 3 -C 9 ) cycloalkyl, ( C 5 -C 9 ) cycloalkenyl, [(CrC 5 ) alkyl] carbonyl, [(CrC 6 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 6 ) alkylamino-carbonyi, di (Cι . -C6) alkylamino carbonyl, (-C-C 6 ) alkylsulfonyl and (CC 6 ) haloalkylsulfonyl is substituted and including substituents preferably has up to 30 C atoms, or
Wasserstoff, (Cι-C6)Alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (Cι-Cβ)Alkoxy, (C2- C6)Alkenyloxy, (C2-C6)Alkinyloxy, (C C6)Alkylthio, (C2-C6)Alkenylthio, (C2- C6)Alkinylthio, (C1-C6)Alkyl-amino oder Di-[(C C6)alkyl]-amino, wobei jeder der letztgenannten 11 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (Cι-C4)Alkoxy, (CrC4)Haloalkoxy, (C2- C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (CrC4)Alkylthio, (d- C4)Alkylsulfinyl, (CrC4)Alkylsulfonyl, (C C4)Haloalkylthio, (Cr C4)Haloalkylsulfinyl, (Cι-C4)Haloalkylsulfonyl, (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, und Reste der Formeln R,-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-, R,R"N-C(=Z')-, R'-Z-C(=Z')-O-, R'R"N-C(=Z,)-Z-, R,-Z-C(=Z')-NR"- und R,R"N-C(=Z,)-NR",-I worin R', R" und R1" jeweils unabhängig voneinander Wasserstoff oder vorzugsweise (Cι-C6)Alkyl, Aryl, Aryl-(CrC6)alkyl, (C3- C9)Cycloalkyl oder (C3-C9)Cycloalkyl~(Cι-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist und inklusive Substituenten vorzugsweise 1 bis 30 C- Atome aufweist, R2 (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist, (C -CΘ)Cycloalkenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, oder Phenyl, das unsubstituiert oder substituiert ist, wobei R2 inklusive Substituenten vorzugsweise bis zu 30 C-Atome aufweist,Hydrogen, (-C-C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Cι-Cβ) alkoxy, (C 2 - C 6 ) alkenyloxy, (C 2 -C 6 ) alkynyloxy, (CC 6) alkylthio, (C 2 -C 6) alkenylthio, (C 2 - C 6) alkynylthio, (C 1 -C 6) alkyl-amino or di - [(CC 6) alkyl] amino, wherein each of the latter 11 residues unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, nitro, thiocyanato, (-C-C 4 ) alkoxy, (CrC4) haloalkoxy, (C 2 - C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (CrC 4 ) alkylthio, (d- C 4 ) alkylsulfinyl, (CrC 4 ) alkylsulfonyl, (CC 4 ) haloalkylthio, (C r C 4 ) haloalkylsulfinyl, (Cι-C 4 ) haloalkylsulfonyl, (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, heterocyclyl which is unsubstituted or substituted, and radicals of the formulas R , -C (= Z ') -, R'-C (= Z') - Z-, R'-ZC (= Z ' ) -, R , R "NC (= Z ') -, R'-ZC (= Z') - O-, R'R" NC (= Z , ) -Z-, R , -ZC (= Z ' ) -NR "- and R , R" NC (= Z , ) -NR " , - I wherein R ', R" and R 1 "are each independently hydrogen or preferably (-C-C 6 ) alkyl, aryl, aryl- (CrC 6 ) alkyl, (C 3 - C 9 ) cycloalkyl or (C 3 -C 9 ) cycloalkyl ~ (Cι-C 6 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, and in which Z and Z ' are each independently an oxygen or sulfur atom, are substituted and, including substituents, preferably have 1 to 30 C atoms, R 2 (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted, (C -C Θ ) cycloalkene nyl which is unsubstituted or substituted, heterocyclyl which is unsubstituted or substituted, or phenyl which is unsubstituted or substituted, where R 2 including substituents preferably has up to 30 C atoms,
R3 eine Gruppe — U* R 3 a group - U *
worinwherein
L1 eine direkte Bindung, -O-, -S- oder eine Gruppe der Formel -NG2-, vorzugsweise eine direkte Bindung,L 1 is a direct bond, -O-, -S- or a group of the formula -NG 2 -, preferably a direct bond,
L)\ U2 unabhängig voneinander eine Gruppe der Formel G3, OG4, SG5,L ) \ U 2 independently of one another a group of the formula G 3 , OG 4 , SG 5 ,
NG6G7, NG8NG9G10, NG11OG12 oder NG11SG12,NG 6 G 7 , NG 8 NG 9 G 10 , NG 11 OG 12 or NG 11 SG 12 ,
U3 eine Gruppe der Formel G13, OG14, SG15, NG16G17, NG18NG19G20,U 3 is a group of the formula G 13 , OG 14 , SG 15 , NG 16 G 17 , NG 18 NG 19 G 20 ,
NG21OG22 oder NG23SG24,NG 21 OG 22 or NG 23 SG 24 ,
U4 eine Gruppe der Formel G25, OG26, SG27 oder NG28G29 bedeuten, wobei die Reste G1 bis G29 unabhängig voneinander Wasserstoff, Aryl, das unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise 6 bis 30 C-Atomen aufweist, oder (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise 3 bis 30 C-Atome aufweist, oder Heterocyclyl, das substituiert oder unsubstituiert ist und inklusive Substituenten vorzugsweise 2 bis 30 C-Atome aufweist, oder (Cι-C6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl bedeuten, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (Cι-C )Alkoxy, (Cι-C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (d-C4)Alkylthio, (C1-C4)Alkylsulfinyl, (Cι-C4)Alkylsulfonyl, (C C4)Haloalkylsulfinyl, (Cι-C4)Haloalkylsulfonyl, (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, und Reste der Formeln R'-C(=Z , R'-C(=Z')-Z-, R'-Z- C(=Z , R'R"N-C(=Z , R'-Z-C(=Z')-O-, R'R"N-C(=Z')-Z-, R'-Z-C(=Z NR"- und R'R"N-C(=Z')-NR"1-, worinU 4 is a group of the formula G 25 , OG 26 , SG 27 or NG 28 G 29 , where the radicals G 1 to G 29 independently of one another are hydrogen, aryl which is unsubstituted or substituted and preferably has 6 to 30 C atoms including substituents, or (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted and preferably including substituents Has 3 to 30 carbon atoms, or heterocyclyl, which is substituted or unsubstituted and including substituents preferably has 2 to 30 carbon atoms, or (-C-C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 - C 6 ) mean alkynyl, where each of the latter 3 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, nitro, thiocyanato, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (dC 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (Cι-C 4 ) alkylsulfonyl, (CC 4 ) haloalkylsulfinyl, (Cι-C 4 ) Haloalkylsulfonyl, (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, H eterocyclyl, which is unsubstituted or substituted, and radicals of the formulas R'-C (= Z, R'-C (= Z ') - Z-, R'-Z- C (= Z, R'R "NC (= Z, R'-ZC (= Z ') - O-, R'R "NC (= Z') - Z-, R'-ZC (= Z NR" - and R'R "NC (= Z ') -NR " 1 -, wherein
R', R" und R'" jeweils unabhängig voneinander Wasserstoff oder vorzugsweise (C C6)Alkyl, Aryl, Aryl-(CrC6)alkyl, (C3-C9)Cycloalkyl oder (C3-C9)Cycloalkyl-(Cι-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten und worin Z und T unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind/substituiert ist und inklusive Substituenten vorzugsweise 1 bis 30 C-Atome aufweist, oder die Reste U1 und U3 oder U2 und ü4 oder U2 und G1 oder U4 und G1 paarweise mit den sie verbindenden Atomen jeweils einen carbocyclischen bzw. heterocyclischen Ring mit 4 bis 7 Ringatomen bedeuten, wobei der Ring unsubstituiert oder substituiert ist, einen Rest der Formel -B1-D1, wobei B1 und D1 wie unten definiert sind und R4 inklusive Substituenten vorzugsweise bis zu 20 C-Atome aufweist, A1 eine direkte Bindung oder geradkettiges Alkylen mit 1 bis 5 C-Atomen oder geradkettiges Alkenylen oder Alkinylen mit jeweils 2 bis 5 C-Atomen, wobei jeder der drei letztgenannten Diradikale unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Cyano, Thiocyanato und Reste der Formel -B2-D2 substituiert ist, wobei B2 und D2 wie unten definiert sind,R ', R "and R'" each independently of one another are hydrogen or preferably (CC 6 ) alkyl, aryl, aryl- (CrC 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 -C 9 ) cycloalkyl- ( C 1 -C 6 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, and in which Z and T are each independently an oxygen or sulfur atom / is substituted and preferably contains 1 to 30 C atoms, including substituents, or the Residues U 1 and U 3 or U 2 and U 4 or U 2 and G 1 or U 4 and G 1 in pairs with the atoms connecting them each represent a carbocyclic or heterocyclic ring with 4 to 7 ring atoms, the ring being unsubstituted or substituted is a radical of the formula -B 1 -D 1 , where B 1 and D 1 are as defined below and R 4, including substituents, preferably has up to 20 C atoms, A 1 is a direct bond or straight-chain alkylene having 1 to 5 carbon atoms or straight-chain alkenylene or alkynylene each having 2 to 5 carbon atoms, each of the three last-mentioned diradicals being unsubstituted or by one or more radicals from the group halogen, nitro, cyano , Thiocyanato and radicals of the formula -B 2 -D 2 , where B 2 and D 2 are as defined below,
A2 eine direkte Bindung oder geradkettiges Alkylen mit 1 bis 4 C-Atomen oder geradkettiges Alkenylen oder Alkinylen mit jeweils 2 bis 5 C-Atomen, wobei jeder der drei letztgenannten Diradikale unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Cyano, Thiocyanato und Reste der Formel -B3-D3 substituiert ist, oder ein divalenter Rest der Formel V1, V2, V3, V4 oder V5,A 2 is a direct bond or straight-chain alkylene having 1 to 4 carbon atoms or straight-chain alkenylene or alkynylene each having 2 to 5 carbon atoms, each of the three last-mentioned diradicals being unsubstituted or by one or more radicals from the group halogen, nitro, cyano , Thiocyanato and radicals of the formula -B 3 -D 3 is substituted, or a divalent radical of the formula V 1 , V 2 , V 3 , V 4 or V 5 ,
CRaRb-W*-CRcRd- (V1)CR a R b -W * -CR c R d - (V 1 )
CRaRb-W*-CRcRd-CReRf- (V2)CR a R b -W * -CR c R d -CR e R f - (V 2 )
•CRaRb-CRcRd-W*-CReRf- (V3)• CR a R b -CR c R d -W * -CR e R f - (V 3 )
•CRaRb-CRcRd-W*- (V4)• CR a R b -CR c R d -W * - (V 4 )
CRaRb-W*- (V5)CR a R b -W * - (V 5 )
wobei jeder der Reste Ra, Rb, Rc, Rd, Re und Rf jeweils unabhängig voneinander Wasserstoff, Halogen, Nitro, Cyano, Thiocyanato oder ein Rest der Formel -B4-D4 ist,wherein each of the radicals R a , R b , R c , R d , R e and R f each independently of one another is hydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula -B 4 -D 4 ,
W* jeweils ein Sauerstoffatom, ein Schwefelatom oder eine Gruppe der Formel N(B5-D5) ist undW * is in each case an oxygen atom, a sulfur atom or a group of the formula N (B 5 -D 5 ) and
B3, B4, B5, D3, D4 und D5 wie unten definiert sind, B1 und B5 jeweils unabhängig voneinander eine direkte Bindung oder eine divalente Gruppe der Formeln -C(=Z*)-, -C(=Z*)-Z**-, -C(=Z*)-NH- oder -C(=Z*)-NR*-, wobei Z* = ein Sauerstoff- oder Schwefelatom, Z** = ein Sauerstoff- oder Schwefelatom und R* = (Cι-C6)Alkyl, Aryl, Aryl-(Cι-C6)alkyl, (C3-C9)Cycloalkyl oder (C3-C9)Cycloalkyl-(Cι-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise bis zu 20 C-Atome aufweist, B2, B3 und B4 jeweils unabhängig voneinander eine direkte Bindung oder eine divalente Gruppe der Formeln -O-, -S(O)p-, -S(O)p-O-, -O-S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR° -, -O-NR0-, -NR°-O-, -NR°-CO-, -CO-NR0-, -O-CO-NR0- oder -NR°-CO-O-, wobei p die ganze Zahl 0, 1 oder 2 ist und R° Wasserstoff, (Cι-C6)Alkyl, Aryl, Aryl-(C C6)alkyl, (C3-C9)Cycloalkyl oder (C3-C9)Cycloalkyl-(C1-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise bis zu 20 C-Atome aufweist, bedeutet, D1, D2, D3, D4 und D5 jeweils unabhängig voneinander Wasserstoff, (Cι-C6)Alkyl,B 3 , B 4 , B 5 , D 3 , D 4 and D 5 are as defined below, B 1 and B 5 each independently of one another a direct bond or a divalent group of the formulas -C (= Z *) -, -C (= Z *) - Z ** -, -C (= Z *) - NH- or -C (= Z *) - NR * -, where Z * = an oxygen or sulfur atom, Z ** = an oxygen - Or sulfur atom and R * = (-C-C 6 ) alkyl, aryl, aryl- (-C-C 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 -C 9 ) cycloalkyl- (Cι-C 6 ) alkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted and preferably including up to 20 C atoms, including substituents, B 2 , B 3 and B 4 each independently of one another are a direct bond or a divalent group of the formulas -O-, -S (O) p -, -S (O) p -O-, -OS (O) p -, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR ° -, -O-NR 0 -, -NR ° -O-, -NR ° -CO-, -CO-NR 0 -, -O-CO-NR 0 - or -NR ° -CO-O-, where p is the integer 0, 1 or 2 and R ° is hydrogen, (-CC 6 ) alkyl, aryl, aryl- (CC 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 -C 9 ) cycloalkyl - (C 1 -C 6 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted and, including substituents, preferably has up to 20 C atoms, means D 1 , D 2 , D 3 , D 4 and D 5 each independently from each other hydrogen, (-CC 6 ) alkyl,
Aryl, Aryl-(C C6)alkyl, (C3-C9)Cycloalkyl oder (C3-C9)Cycloalkyl-(Cι-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise bis zu 20 C-Atome aufweist, oder jeweils zwei Reste D3 von an einem C-Atom gebundenen zwei Gruppen -B3-D3 miteinander verbunden sind und eine Alkylengruppe mit 2 bis 4 C- Atomen ergeben, die unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe (CrC4)Alkyl und (C1-C4)Alkoxy substituiert ist, L° eine direkte Bindung, Sauerstoff, Schwefel oder eine Gruppe NG30, worin der Rest G30 Aryl, aryl- (CC 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 -C 9 ) cycloalkyl- (Cι-C 6 ) alkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted and including substituents preferably has up to 20 carbon atoms, or two radicals D 3 of two groups -B 3 -D 3 bonded to a carbon atom are connected to one another and give an alkylene group having 2 to 4 carbon atoms which are unsubstituted or by one or several radicals from the group (CrC 4 ) alkyl and (C 1 -C 4 ) alkoxy is substituted, L ° is a direct bond, oxygen, sulfur or a group NG 30 , where the radical G 30
Wasserstoff, Aryl, das unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise 6 bis 30 C-Atomen aufweist, oder (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise 3 bis 30 C-Atome aufweist, oder Heterocyclyl, das substituiert oder unsubstituiert ist und inklusive Substituenten vorzugsweise 2 bis 30 C-Atome aufweist, oder (Cι-C6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (Cι-C4)Alkoxy, (C-ι-C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (Cι-C4)Alkylthio, (CrC4)Alkylsulfinyl, (CrC4)Alkylsulfonyl, (C C4)Haloalkylsulfinyl, (Cι-C4)Haloalkylsulfonyl, (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, und Reste der Formeln R'-C(=Z , R'-C(=Z')-Z-, R'-Z- C(=Z')-, R'R"N-C(=Z')-, R'-Z-C(=Z')-O-, R'R"N-C(=Z')-Z-, R'-Z-C(=Z NR"- und R'R"N-C(=Z')-NR'"-, worinHydrogen, aryl which is unsubstituted or substituted and preferably has 6 to 30 C atoms including substituents, or (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted and preferably has 3 to 30 C atoms including substituents, or heterocyclyl , which is substituted or unsubstituted and including substituents preferably has 2 to 30 C atoms, or (-C-C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 unsubstituted radicals or by one or more radicals from the group halogen, hydroxy, cyano, nitro, thiocyanato, (Cι-C 4) alkoxy, (Cι-C 4) haloalkoxy, (C 2 -C 4) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (-C-C 4 ) alkylthio, (CrC 4 ) alkylsulfinyl, (CrC 4 ) alkylsulfonyl, (CC 4 ) haloalkylsulfinyl, (Cι-C 4 ) haloalkylsulfonyl, (C 3 -C 9 ) cycloalkyl, which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, heterocyclyl which is unsubstituted or is substituted, and radicals of the formulas R'-C (= Z, R'-C (= Z ') - Z-, R'-Z- C (= Z') -, R'R "NC (= Z ' ) -, R'-ZC (= Z ') - O-, R'R "NC (= Z') - Z-, R'-ZC (= Z NR" - and R'R "NC (= Z ' ) -NR '"-, where
R', R" und R'" jeweils unabhängig voneinander Wasserstoff oder vorzugsweise (C C6)Alkyl, Aryl, Aryl-(C1-C6)alkyl, (C3-C9)Cycloalkyl oder (Cs-CgJCycloalkyKC-i-CeJalkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist und inklusive Substituenten vorzugsweise 1 bis 30 C- Atome aufweist, (X)n n Substituenten X und dabei X jeweils unabhängig voneinander Halogen,R ', R "and R'" each independently of one another are hydrogen or preferably (CC 6 ) alkyl, aryl, aryl- (C 1 -C 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (Cs-CgJCycloalkyKC-i- CeJalkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, and in which Z and Z 'are each independently an oxygen or sulfur atom, are substituted and, including substituents, preferably have 1 to 30 C atoms, (X) nn substituents X and X is independently halogen,
Hydroxy, Amino, Nitro, Formyl, Carboxy, Cyano, Thiocyanato, Aminocarbonyl oder (Cι-C6)Alkyl, (CrC6)Alkoxy, (Cι-C6)Alkylthio, Mono(CrC6)alkylamino, Di(C1-C4)alkylamino, (C2-C6)Alkenyl, (C2-C6)Alkinyl, [(C1-C6)Alkyl]carbonyl, [(Cι-C6)Alkoxy]carbonyl, Mono(Cι-C6)alkylamino-carbonyl Di(CrC4)alkylamino-carbonyl, N-(Cι-C6)Alkanoyl-amino oder N-(C C4)Alkanoyl-N-(Cι-C4)alkyl-amino, wobei jeder der letztgenannten 13 Reste unsubstituiert oder substituiert ist, vorzugsweise unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Cyano, Thiocyanato, (CrC )Alkoxy, (Cι-C4)Haloalkoxy, (C C4)Alkylthio, (C1-C4)Haloalkylthio, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (C3-C9)Cycloalkyl, (C3-Cg)Cycloalkyl-amino, [(CrC4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(Cι-C4)alkylamino-carbonyl, Phenyl, Phenoxy, Phenylthio, Phenylcarbonyl, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio und Heterocyciylamino, wobei jeder der letztgenannten 8 Reste unsubstituiert ist oder einen oder mehrere Substituenten aus der Gruppe Halogen, Nitro, Cyano, (C|-C4)Alkyl, (CrC4)Alkoxy, (CrC4)Alkylthio, (C1-C4)Haloalkyl, (Cι-C4)Haloalkoxy, Formyl, (Cι-C4)Alkyl-carbony und (C-ι-C4)Alkoxy- carbonyl aufweist, substituiert ist, oder (C3-C9)Cycloalkyl, (C3-Cg)Cycloalkoxy, (C3-C9)Cycloalkylamino, Phenyl, Phenoxy, Phenylthio, Phenylcarbonyl, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio oder Heterocyciylamino, wobei jeder der letztgenannten 11 Reste unsubstituiert oder substituiert ist, vorzugsweise unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Cyano, Thiocyanato, (Cι-C4)Alkyl, (Cι-C4)Haloalkyl, (C C4)Alkoxy, (CrC4)Haloalkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkylthio, Mono(Cι-C4)alkylamino, Di(C1-C4)alkylamino, (C3-C9)Cycloalkyl, [(C -C4)Alkyl]carbonyl, [(Ci -C4)AI koxyjcarbonyl , Aminocarbonyl , Mono(Cι-C )alkylamino-carbonyl und Di(CrC4)alkylamino- carbonyl substituiert ist, oder zwei benachbarte Reste X gemeinsam einen ankondensierten Cyclus mit 4 bis 6 Ringatomen, der carbocyclisch ist oder Heteroringatome aus der Gruppe O, S und N enthält und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (CrC4)Alkyl und Oxo substituiert ist, n 0, 1 , 3, 4 oder 5, vorzugsweise 0, 1 , 2, 3 oder 4, insbesondere 0, 1 oder 2, und Heterocyclyl in den vorstehend genannten Resten unabhängig voneinander jeweils einen heterocyclischen Rest mit 3 bis 7 Ringatomen und 1 bis 3 Heteroatomen aus der Gruppe N, O und S bedeuten.Hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, aminocarbonyl or (Cι-C 6 ) alkyl, (CrC 6 ) alkoxy, (Cι-C 6 ) alkylthio, mono (CrC 6 ) alkylamino, di (C 1 - C 4 ) alkylamino, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, [(C 1 -C 6 ) alkyl] carbonyl, [(Cι-C 6 ) alkoxy] carbonyl, mono (Cι- C 6 ) alkylamino-carbonyl di (CrC 4 ) alkylamino-carbonyl, N- (-C-C 6 ) alkanoyl-amino or N- (C C4) alkanoyl-N- (Cι-C 4 ) alkyl-amino, each of which the latter 13 radicals is unsubstituted or substituted, preferably unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, (CrC) alkoxy, (C 1 -C 4 ) haloalkoxy, (CC 4 ) alkylthio, (C 1 -C 4 ) haloalkylthio, mono (-C-C 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, (C 3 -Cg) cycloalkyl-amino, [(CrC 4 ) alkyl] carbonyl, [(-C-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino-carbonyl, di (Cι-C 4 ) alkylamino-carbonyl, phenyl, phenoxy, phenylthio, Phenylcarbon yl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyciylamino, where each of the latter 8 residues is unsubstituted or one or more substituents from the group halogen, nitro, cyano, (C | -C 4 ) alkyl, (CrC 4 ) alkoxy, (CrC 4 ) Alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy, formyl, (C 1 -C 4 ) alkylcarbonyl and (C 1 -C 4 ) alkoxycarbonyl, is substituted, or (C 3 -C 9 ) cycloalkyl, (C 3 - Cg) cycloalkoxy, (C 3 -C 9 ) cycloalkylamino, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyciylamino, each of the latter 11 radicals being unsubstituted or substituted, preferably unsubstituted or by one or more Group halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, (-C-C 4 ) alkyl, (Cι-C 4 ) haloalkyl, (CC 4 ) alkoxy, (CrC 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkylthio, mono (Cι-C 4 ) alkylamino, di (C 1 -C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C -C 4 ) alkyl] carbonyl, [(Ci -C 4 ) Al koxyjcarbonyl, aminocarbonyl, mono (-C-C) alkylamino-carbonyl and di (CrC 4 ) alkylamino-carbonyl, or two adjacent radicals X together a fused-on cycle with 4 to 6 ring atoms, which is carbocyclic contains t or hetero ring atoms from the group O, S and N and which is unsubstituted or substituted by one or more radicals from the group halogen, (CrC 4 ) alkyl and oxo, n 0, 1, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in particular 0, 1 or 2, and heterocyclyl in the radicals mentioned above each independently represent a heterocyclic radical with 3 to 7 ring atoms and 1 to 3 heteroatoms from the group N, O and S.
Wenn nicht näher angegeben, sind divalente Reste, z.B. B1 = -C(=Z*)-Z**-, so definiert, daß in den zusammengesetzten Gruppen, z. B. - B1-D1, diejenige Bindung des divalenten Restes mit der Gruppe D1 verbunden ist, die in der Formel für den divalenten Rest rechts geschrieben ist, d. h. - B1-D1 ist eine Gruppe der Formel -C(=Z*)-Z**-D1; entsprechendes gilt für analoge divalente Reste. Die Verbindungen der Formel (I) können durch Anlagerung einer geeigneten anorganischen oder organischen Säure, wie beispielsweise HCI, HBr, H2SO4 oder HNO3, aber auch Oxalsäure oder Sulfonsäuren an eine basische Gruppe, wie z.B. Amino oder Alkylamino, Salze bilden. Geeignete Substituenten, die in deprotonierter Form, wie z.B. Sulfonsäuren oder Carbonsäuren, vorliegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. Salze können ebenfalls dadurch gebildet werden, daß bei geeigneten Substituenten, wie z.B. Sulfonsäuren oder Carbonsäuren, der Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird. Diese Salze sind beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre (quatemäre) Ammoniumsalze.If not specified, divalent radicals, for example B 1 = -C (= Z *) - Z ** -, are defined so that in the composite groups, for. B. - B 1 -D 1 , that bond of the divalent radical to the group D 1 which is written in the formula for the divalent radical on the right, ie - B 1 -D 1 is a group of the formula -C (= Z *) - Z ** - D 1 ; the same applies to analog divalent residues. The compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, for example HCl, HBr, H 2 SO 4 or HNO 3 , but also oxalic acid or sulfonic acids to a basic group, such as amino or alkylamino. Suitable substituents which are present in deprotonated form, such as, for example, sulfonic acids or carboxylic acids, can form internal salts with groups which can be protonated, such as amino groups. Salts can also be formed in that, in the case of suitable substituents, such as, for example, sulfonic acids or carboxylic acids, the hydrogen is replaced by a cation which is suitable for agriculture. These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts.
In Formel (I) und allen nachfolgenden Formeln können die Reste Alkyl, Alkoxy, Haloalkyl, Haloalkoxy, Alkylamino und Alkylthio sowie die entsprechenden ungesättigten und/oder substituierten Reste im Kohlenstoffgerüst jeweils geradkettig oder verzweigt sein. Wenn nicht speziell angegeben, sind bei diesen Resten die niederen Kohlenstoffgerüste, z.B. mit 1 bis 6 C-Atomen bzw. bei ungesättigten Gruppen mit 2 bis 6 C-Atomen, bevorzugt. Alkylreste, auch in den zusammengesetzten Bedeutungen wie Alkoxy, Haloalkyl usw., bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1 ,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1 -Methylhexyl und 1,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste; Alkenyl bedeutet z.B. Allyl, 1-Methylprop-2-en-1-yl, 2-Methyl-prop-2-en-1-yl, But-2-en-1-yl, But-3-en-1-yl, 1-Methyl-but-3-en-1-yl und 1-Methyl-but-2-en-1-yl; Alkinyl bedeutet z.B. Propargyl, But-2-in-1-yl, But-3-in-1-yl, 1-Methyl-but-3-in-1-yl.In formula (I) and all the following formulas, the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and / or substituted radicals in the carbon skeleton can each be straight-chain or branched. Unless specifically stated, the lower carbon skeletons, e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred. Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl etc., mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; Alkenyl means e.g. Allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1- Methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl; Alkynyl means e.g. Propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-yl.
Cycloalkyl bedeutet ein carbocyclisches, gesättigtes Ringsystem mit vorzugsweise 3-8 C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. Im Falle von substituiertem Cycloalkyl werden cyclische Systeme mit Substituenten umfaßt, wobei die Substituenten mit einer Doppelbindung am Cycloalkylrest, z. B. eine Alkylidengruppe wie Methyliden, gebunden sind. Im Falle von substituiertem Cycloalkyl werden auch mehrcyclische aliphatische Systeme umfaßt, wie beispielsweise Bicyclo[1.1.0]butan-1-yl, Bicyclo[1.1.0]butan-2-yl, Bicyclo[2.1.0]pentan-1-yl, Bicyclo[2.1.0]pentan-2-yl, Bicyclo[2.1.0]pentan-5-yl, Adamantan-1-yl und Adamantan-2-yl.Cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 C atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. In the event of of substituted cycloalkyl cyclic systems with substituents are included, the substituents having a double bond on the cycloalkyl radical, e.g. B. an alkylidene group such as methylidene. In the case of substituted cycloalkyl, multi-cyclic aliphatic systems are also included, such as, for example, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, Bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, adamantan-1-yl and adamantan-2-yl.
Cycloalkenyl bedeutet ein carbocyclisches, nicht aromatisches, partiell ungesättigtes Ringsystem mit vorzugsweise 4-8 C-Atomen, z.B. 1-Cyclobutenyl, 2-Cyclobutenyl, 1- Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, oder 1-Cyclohexenyl, 2- Cyclohexenyl, 3-Cyclohexenyl, 1 ,3-Cyclohexadienyl oder 1 ,4-Cyclohexadienyl. Im Falle von substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend.Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl. In the case of substituted cycloalkenyl, the explanations for substituted cycloalkyl apply accordingly.
Halogen bedeutet beispielsweise Fluor, Chlor, Brom oder lod. Haloalkyl, -alkenyl und -alkinyl bedeuten durch Halogen, vorzugsweise durch Fluor, Chlor und/oder Brom, insbesondere durch Fluor oder Chlor, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl (= Monohalogenalkyl), Perhaloalkyl, CF3> CHF2, CH2F, CF3CF2, CH2FCHCI, CCI3, CHCI2, CH2CH2CI; Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3 und OCH2CH2CI; entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierte Reste.Halogen means, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are partially or fully substituted alkyl, alkenyl or alkynyl, for example monohaloalkyl (= monohalogenalkyl), perhaloalkyl, CF 3> by halogen, preferably by fluorine, chlorine and / or bromine, in particular by fluorine or chlorine CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCI, CCI 3 , CHCI 2 , CH 2 CH 2 CI; Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
Aryl bedeutet ein mono-, bi- oder polycyclisches aromatisches System, beispielsweise Phenyl, Naphthyl, Tetrahydronaphthyl, Indenyl, Indanyl, Pentalenyl, Fluorenyl und ähnliches, vorzugsweise Phenyl.Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
Ein heterocyclischer Rest oder Ring (Heterocyclyl) kann gesättigt, ungesättigt oder heteroaromatisch sein; er enthält vorzugsweise ein oder mehrere, insbesondere 1 , 2 oder 3 Heteroatome im heterocyclischen Ring, vorzugsweise aus der Gruppe N, O, und S; vorzugsweise ist er ein aliphatischer Heterocyclylrest mit 3 bis 7 Ringatomen oder ein heteroaromatischer Rest mit 5 oder 6 Ringatomen. Der heterocyclische Rest kann z.B. ein heteroaromatischer Rest oder Ring (Heteroaryl) sein, wie z.B. ein mono-, bi- oder polycyclisches aromatisches System, in dem mindestens 1 Ring ein oder mehrere Heteroatome enthält, beispielsweise Pyridyl, Pyrimidinyl, Pyridazinyl, Pyrazinyl, Triazinyl, Thienyl, Thiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Furyl, Pyrrolyl, Pyrazolyl, Imidazolyl und Triazolyl, oder ist ein partiell oder vollständig hydrierter Rest wie Oxiranyl, Oxetanyl, Oxolanyl (= Tetrahydrofuryl), Oxanyl, Pyrrolidyl, Piperidyl, Piperazinyl, Dioxolanyl, Oxazolinyl, Isoxazolinyl, Oxazolidinyl, Isoxazolidinyl und Morpholinyl. Als Substituenten für einen substituierten heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo. Die Oxogruppe kann auch an den Heteroringatomen, die in verschiedenen Oxidationsstufen existieren können, z.B. bei N und S, auftreten.A heterocyclic radical or ring (heterocyclyl) can be saturated, unsaturated or heteroaromatic; it preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms. The heterocyclic radical can be, for example, a heteroaromatic radical or ring (heteroaryl), such as, for example, a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, Thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl, imidazolyl and triazolyl, or is a partially or completely hydrogenated radical such as oxiranyl, oxetanyl, oxolanyl (= tetrahydrofuryl), oxanyl, pyrrolidylolazidyl, piperyl , Isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl. Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and additionally oxo. The oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example in the case of N and S.
Substituierte Reste, wie ein substituierter Alkyl-, Alkenyl-, Alkinyl-, Aryl-, Phenyl-, Benzyl-, Heterocyclyl- und Heteroarylrest, bedeuten beispielsweise einen vom unsubstituierten Grundkörper abgeleiteten substituierten Rest, wobei die Substituenten beispielsweise einen oder mehrere, vorzugsweise 1 , 2 oder 3 Reste aus der Gruppe Halogen, Alkoxy, Haloalkoxy, Alkylthio, Hydroxy, Amino, Nitro, Carboxy, Cyano, Azido, Alkoxycarbonyl, Alkylcarbonyl, Formyl, Carbamoyl, Mono- und Dialkylaminocarbonyl, substituiertes Amino, wie Acylamino, Mono- und Dialkylamino, und Alkylsuifinyl, Haloalkylsulfinyi, Alkylsulfonyl, Haloalkylsulfonyl und, im Falle cyclischer Reste, auch Alkyl und Haloalkyl bedeuten. Dabei bedeuten in der Definition "einen oder mehrere Reste aus der Gruppe" jeweils einen oder mehrere gleiche oder verschiedene Reste aus der genannten Gruppe von Resten, sofern nicht spezielle Einschränkungen ausdrücklich definiert sind. Im Begriff "substituierte Reste" wie substituiertes Alkyl etc. sind als Substituenten zusätzlich zu den genannten gesättigten kohlenwasserstoffhaltigen Resten entsprechende ungesättigte aliphatische und aromatische Reste, wie gegebenenfalls substituiertes Alkenyl, Alkinyl, Alkenyloxy, Alkinyloxy, Phenyl, Phenoxy etc. eingeschlossen. Im Falle von substituierten cyclischen Resten mit aliphatischen Anteilen im Ring werden auch cyclische Systeme mit solchen Substituenten umfaßt, die mit einer Doppelbindung am Ring gebunden sind, z. B. mit einer Alkylidengruppe wie Methyliden oder Ethyliden substituiert sind.Substituted radicals, such as a substituted alkyl, alkenyl, alkynyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, mean, for example, a substituted radical derived from the unsubstituted basic body, the substituents being, for example, one or more, preferably 1, 2 or 3 radicals from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino , and Alkylsuifinyl, Haloalkylsulfinyi, Alkylsulfonyl, Haloalkylsulfonyl and, in the case of cyclic radicals, also mean alkyl and haloalkyl. In the definition "one or more radicals from the group" mean one or more identical or different radicals from the group of radicals mentioned, unless specific restrictions are expressly defined. The term "substituted radicals" such as substituted alkyl etc. includes, in addition to the saturated hydrocarbon-containing radicals mentioned, corresponding unsaturated aliphatic and aromatic radicals, such as optionally substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy etc. In the case of substituted cyclic radicals with aliphatic portions in the ring, cyclic systems with such substituents are also included, which are bonded to the ring with a double bond, e.g. B. are substituted with an alkylidene group such as methylidene or ethylidene.
Bei Resten mit C-Atomen sind solche mit 1 bis 4 C-Atomen, insbesondere 1 oder 2 C-Atomen, bevorzugt. Bevorzugt sind in der Regel Substituenten aus der Gruppe Halogen, z.B. Fluor und Chlor, (Cι-C4)Alkyl, vorzugsweise Methyl oder Ethyl, (Cι-C )Haloalkyl, vorzugsweise Trifluormethyl, (CrC )Alkoxy, vorzugsweise Methoxy oder Ethoxy, (Cι-C )Haloalkoxy, Nitro und Cyano. Besonders bevorzugt sind dabei die Substituenten Methyl, Methoxy und Chlor.In the case of radicals with carbon atoms, those with 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred. Preferred are generally substituents from the group halogen, for example fluorine and chlorine, (-CC 4 ) alkyl, preferably methyl or ethyl, (-C-C) haloalkyl, preferably trifluoromethyl, (CrC) alkoxy, preferably methoxy or ethoxy, ( Cι-C) haloalkoxy, nitro and cyano. The substituents methyl, methoxy and chlorine are particularly preferred.
Mono- oder disubstituiertes Amino bedeutet einen chemisch stabilen Rest aus der Gruppe der substituierten Aminoreste, welche beispielsweise durch einen bzw. zwei gleiche oder verschiedene Reste aus der Gruppe Alkyl, Alkoxy, Acyl und Aryl N-substituiert sind; vorzugsweise Monoalkylamino, Dialkylamino, Acylamino, Arylamino, N-Alkyl-N-arylamino sowie N-Heterocyclen; dabei sind Alkylreste mit 1 bis 4 C-Atomen bevorzugt; Aryl ist dabei vorzugsweise Phenyl oder substituiertes Phenyl; für Acyl gilt dabei die weiter unten genannte Definition, vorzugsweise (Cι-C4)Alkanoyi. Entsprechenes gilt für substituiertes Hydroxylamino oder Hydrazino.Mono- or disubstituted amino means a chemically stable radical from the group of substituted amino radicals which are, for example, N-substituted by one or two identical or different radicals from the group alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles; alkyl radicals having 1 to 4 carbon atoms are preferred; Aryl is preferably phenyl or substituted phenyl; the definition given below applies to acyl, preferably (C 1 -C 4 ) alkanoyi. The same applies to substituted hydroxylamino or hydrazino.
Gegebenenfalls substituiertes Phenyl ist vorzugsweise Phenyl, das unsubstituiert oder ein- oder mehrfach, vorzugsweise bis zu dreifach durch gleiche oder verschiedene Reste aus der Gruppe Halogen, (Cι-C4)Alkyl, (CrC4)Alkoxy, (Cι-C4)Halogenalkyl, (CrC4)Halogenalkoxy und Nitro substituiert ist, z.B. o-, m- und p-Tolyl, Dimethylphenyle, 2-, 3- und 4-Chlorphenyi, 2-, 3- und 4-Trifluor- und -Trichlorphenyl, 2,4-, 3,5-, 2,5- und 2,3-Dichlorphenyl, o-, m- und p-Methoxy phenyl.Optionally substituted phenyl is preferably phenyl which is unsubstituted or one or more times, preferably up to three times, by the same or different radicals from the group halogen, (-C 4 -C) alkyl, (CrC 4 ) alkoxy, (-C 4 ) haloalkyl , (CrC 4 ) haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and trichlorophenyl, 2, 4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxy phenyl.
Ein Acylrest bedeutet in einem weiten Sinne den Rest einer organischen Säure, der formal durch Abtrennen einer OH-Gruppe entsteht, z.B. den Rest einer Carbonsäure und Reste davon abgeleiteter Säuren wie der Thiocarbonsäure, gegebenenfalls N-substituierten Iminocarbonsäuren oder den Rest von Kohlensäuremonoestern, gegebenenfalls N-substituierter Carbaminsäure, Sulfonsäuren, Sulfinsäuren, Phosphonsäuren, Phosphinsäuren. Acyl bedeutet beispielsweise Formyl, Alkylcarbonyl wie [(C1-C4)Alkyl]-carbonyl, Phenylcarbonyl, Alkyloxycarbonyl, Phenyloxycarbonyl, Benzyloxycarbonyl, Alkylsulfonyl, Alkylsulfinyl, N-Alkyl-1-iminoalkyl und andere Reste von organischen Säuren. Dabei können die Reste jeweils im Alkyl- oder Phenylteil noch weiter substituiert sein, beispielsweise im Alkylteil durch ein oder mehrere Reste aus der Gruppe Halogen, Alkoxy, Phenyl und Phenoxy; Beispiele für Substituenten im Phenylteil sind die bereits weiter oben allgemein für substituiertes Phenyl erwähnten Substituenten. Im engeren Sinne bedeutet Acyl beispielsweise den Rest einer Alkansäure, Alkensäure, Alkinsäure, Arylcarbonsäure (z. B. Benzoyl), Alkoxycarbonyl, Alkenyloxycarbonyl, Alkinyloxycarbonyl, Aryloxycarbonyl, Alkylsulfonyl oder Alkysulfinyl; in noch engerem Sinne bedeutet Acyl einen Rest einer Alkansäure, z. B. einer (C C24)Alkansäure, vorzugsweise (Cι-Cιs)Alkansäure, insbesondere (CrC-ι2)Alkansäure, ganz besonders (Ci-CβJAlkansäure wie Formyl, Acetyl oder Propionyl.An acyl radical in a broad sense means the residue of an organic acid which is formally formed by removing an OH group, for example the residue of a carboxylic acid and residues of acids derived therefrom, such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the rest of carbonic acid monoesters, optionally N -substituted carbamic acid, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids. Acyl means, for example, formyl, alkylcarbonyl such as [(C 1 -C 4 ) alkyl] carbonyl, phenylcarbonyl, alkyloxycarbonyl, Phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other residues of organic acids. The radicals in each case in the alkyl or phenyl part can be further substituted, for example in the alkyl part by one or more radicals from the group halogen, alkoxy, phenyl and phenoxy; Examples of substituents in the phenyl part are the substituents already mentioned above generally for substituted phenyl. In the narrower sense, acyl means, for example, the remainder of an alkanoic acid, alkenoic acid, alkynic acid, arylcarboxylic acid (e.g. benzoyl), alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkylsulfonyl or alkysulfinyl; in an even narrower sense, acyl means a residue of an alkanoic acid, e.g. B. a (CC 24 ) alkanoic acid, preferably (-C-Cιs) alkanoic acid, in particular (CrC-ι 2 ) alkanoic acid, very particularly (Ci-CβJalkanoic acid such as formyl, acetyl or propionyl.
Die allgemeinen Formeln können formal durch Kombination von Variablen instabile funktionelle Gruppen definieren, z.B. den Carbamylrest oder den Hydroxycarbonyloxyrest, welche im neutralen oder sauren wäßrigen Milieu instabil sind und daher nicht bevorzugt bzw. nur in Form ihrer stabilen Salze oder Abbauprodukte eingesetzt werden.The general formulas can formally define unstable functional groups by combining variables, e.g. the carbamyl radical or the hydroxycarbonyloxy radical, which are unstable in the neutral or acidic aqueous medium and are therefore not preferred or are used only in the form of their stable salts or degradation products.
Gegenstand der Erfindung sind auch alle Stereoisomeren, die von Formel (I) umfasst sind, und deren Gemische. Solche Verbindungen der Formel (I) enthalten ein oder mehrere asymmetrische C-Atome oder auch Doppelbindungen, die in den allgemeinen Formeln (I) nicht gesondert angegeben sind. Die durch ihre spezifische Raumform definierten möglichen Stereoisomeren, wie Enantiomere, Diastereomere, Z- und E-Isomere sind alle von der Formel (I) umfaßt und können nach üblichen Methoden aus Gemischen der Stereoisomeren erhalten oder auch durch stereoselektive Reaktionen in Kombination mit dem Einsatz von stereochemisch reinen Ausgangsstoffen hergestellt werden.The invention also relates to all stereoisomers which are encompassed by formula (I) and mixtures thereof. Such compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds which are not indicated separately in the general formulas (I). The possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I) and can be obtained from mixtures of the stereoisomers by customary methods or else by stereoselective reactions in combination with the use of stereochemically pure starting materials can be produced.
Vor allem aus den Gründen der höheren herbiziden Wirkung, besseren Selektivität und/oder besseren Herstellbarkeit sind erfindungsgemäße Verbindungen der genannten Formel (I) oder deren Salze von besonderem Interesse, worin einzelne Reste eine der bereits genannten oder im Folgenden genannten bevorzugten Bedeutungen haben, oder insbesondere solche, worin eine oder mehrere der bereits genannten oder im folgenden genannten bevorzugten Bedeutungen kombiniert auftreten.Compounds according to the invention are, especially for the reasons of the higher herbicidal activity, better selectivity and / or better manufacturability Formula (I) mentioned or its salts of particular interest, in which individual radicals have one of the preferred meanings already mentioned or mentioned below, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.
R1 ist vorzugsweise Phenyl, Phenoxy, Phenylthio, Phenylamino, N-Phenyl-N-(Cι- C )alkyl-amino, wobei jeder der letztgenannten 5 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (CrC4)Alkyl, (C1-C4)Haloalkyl, (C C4)Alkoxy, (C1-C4)Haloalkoxy, (Cι-C4)Alkylthio, (C1-C4)Haloalkylthio, Mono(C1-C4)alkylamino, Di(Cι-C4)alkylamino, (C3-C9)Cycloalkyl, [(C1-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(Cι-C4)alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl und (CrC4)Haloalkylsulfonyl substituiert ist und inklusive Substituenten 6 bis 30 C-Atome, vorzugsweise 6 bis 20 C-Atome, insbesondere 6 bis 15 C-Atome aufweist. Insbesondere ist R dabei Phenyl, das unsubstituiert oder substituiert ist.R 1 is preferably phenyl, phenoxy, phenylthio, phenylamino, N-phenyl-N- (Cι- C) alkyl-amino, each of the latter 5 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro , Formyl, carboxy, sulfo, cyano, thiocyanato, (CrC 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (CC 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (Cι-C 4 ) alkylthio, ( C 1 -C 4 ) haloalkylthio, mono (C 1 -C 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C 1 -C 4 ) alkyl] carbonyl, [( -C-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (-C-C 4 ) alkylamino-carbonyl, di (Cι-C 4 ) alkylamino-carbonyl, (Cι-C 4 ) alkylsulfonyl and (CrC 4 ) haloalkylsulfonyl is substituted and inclusive Has substituents from 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, in particular 6 to 15 carbon atoms. In particular, R is phenyl which is unsubstituted or substituted.
R1 ist vorzugsweise auch (C3-C9)Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Thiocyanato, (C C4)Alkyl, (C C )Haloalkyl, (C C4)Alkoxy, (Cι-C4)Haloalkoxy, (C C4)Alkylthio, (Cι-C )Haloalkylthio, Mono(Cι-C )alkylamino und Di(Cι-C )alkylamino substituiert ist und inklusive Substituenten 3 bis 30 C-Atome, vorzugsweise 3 bis 20 C-Atome, insbesondere 3 bis 15 C-atome aufweist. Insbesondere ist R1 dabei (C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist.R 1 is preferably also (C 3 -C 9 ) cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (CC 4 ) alkyl, (CC) haloalkyl, (CC 4 ) Alkoxy, (-C-C 4 ) haloalkoxy, (CC 4 ) alkylthio, (Cι-C) haloalkylthio, mono (Cι-C) alkylamino and di (Cι-C) alkylamino is substituted and including substituents 3 to 30 C-atoms, preferably has 3 to 20 carbon atoms, in particular 3 to 15 carbon atoms. In particular, R 1 is (C 3 -C 6 ) cycloalkyl which is unsubstituted or substituted.
R1 ist vorzugsweise auch Heterocyclyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (CrC4)Alkyl, (CrC )Haloalkyl, (Cι-C4)Alkoxy, (C C4)Haloalkoxy, (Cι-C4)Alkylthio, (Cι-C4)Haloalkylthio, Mono d-G alkylamino, Di(C1-C4)alkylamino, (C3-C9)Cycloalkyl, [(Cι-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(C1-C )alkylamino-carbonyl, Di(CrC4)alkylamino-carbonyl, (C C4)Alkylsulfonyl und (C1-C4)Haloalkylsulfonyl substituiert ist und inklusive Substituenten 2 bis 30 C-Atome, vorzugsweise 2 bis 20 C-Atome, insbesondere 2 bis 15 C-atome aufweist.R 1 is preferably also heterocyclyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (CrC 4 ) alkyl, (CrC) haloalkyl, (Cι- C 4 ) alkoxy, (CC 4 ) haloalkoxy, (-C-C 4 ) alkylthio, (Cι-C 4 ) haloalkylthio, mono dG alkylamino, di (C 1 -C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C 1 -C 4 ) alkyl] carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (C 1 -C) alkylamino-carbonyl, Di (CrC 4 ) alkylamino-carbonyl, (CC 4 ) alkylsulfonyl and (C 1 -C 4 ) haloalkylsulfonyl is substituted and including substituents 2 to 30 C atoms, preferably 2 to 20 C atoms, in particular 2 to 15 C atoms having.
Dabei und auch in anderen Resten ist Heterocyclyl wie weiter oben allgemein bzw. vorzugsweise definiert.Here and also in other radicals, heterocyclyl is generally or preferably defined as described above.
Insbesondere ist Heterocyclyl dabei vorzugsweise ein heterocyclischer Rest mit 3 bis 7, insbesondere 3 bis 6 Ringatomen und einem Heteroatom aus der Gruppe N, O und S, beispielsweise Pyridyl, Thienyl, Furyl, Pyrrolyl, Oxiranyl, Oxetanyl, Oxolanyl (= Tetrahydrofuryl), Oxanyl, Pyrrolidyl, Piperidyl, oder ist ein heterocyclischer Rest mit zwei oder drei Heteroatomen aus der Gruppe Pyrimidinyl, Pyridazinyl, Pyrazinyl, Triazinyl, Thienyl, Thiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Pyrazolyl, Triazolyl, Piperazinyl, Dioxolanyl, Oxazolinyl, Isoxazolinyl, Oxazolidinyl, Isoxazolidinyl, Morpholinyl.In particular, heterocyclyl is preferably a heterocyclic radical having 3 to 7, in particular 3 to 6 ring atoms and a heteroatom from the group N, O and S, for example pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, oxetanyl, oxolanyl (= tetrahydrofuryl), oxanyl , Pyrrolidyl, piperidyl, or is a heterocyclic radical having two or three heteroatoms from the group pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, piperazinyl, oxolinylazoxazoloxazoloxazoloxazoloxazoloxazoloxazoloxazoloxazole Isoxazolidinyl, morpholinyl.
R1 ist vorzugsweise auch Wasserstoff oder insbesondere (Cι-C6)Alkyl, (C2- C6)Alkenyl, (C2-C6)Alkinyl, (C1-C6)Alkoxy oder (C1-C6)Alkylthio, wobei jeder der letztgenannten 5 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (Cr C4)Alkoxy, (Cι-C )Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (C C4)Alkylthio, (C1-C4)Alkylsulfinyl, (C C4)Alkylsulfonyl, (C C4)Haloalkylsulfinyl, (d- C4)Haloalkylsulfonyl undR 1 is also preferably hydrogen or in particular (Cι-C6) alkyl, (C 2 - C 6) alkenyl, (C 2 -C 6) alkynyl, (C 1 -C 6) alkoxy or (C 1 -C 6) Alkylthio, each of the last 5 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, nitro, thiocyanato, (Cr C 4 ) alkoxy, (Cι-C) haloalkoxy, (C 2 -C 4 ) alkenyloxy , (C 2 -C 4 ) haloalkenyloxy, (CC 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (CC 4 ) alkylsulfonyl, (CC 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkylsulfonyl and
(C3-C6)Cycloalkyl, das unsubstituiert oder oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Thiocyanato, (Cι-C4)Alkyl, (CrC4)Haloalkyl, (CrC4)Alkoxy, (CrC4)Haloalkoxy, (Cι-C4)Alkylthio, (C C4)Haloalkylthio, Mono(CrC4)alkylamino und Di(CrC4)alkylamino substituiert ist, und Phenyl und Heterocyclyl, wobei jeder der zwei letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (Cι-C4)Alkyl, (C C )Haloalkyl, (CrC4)Alkoxy, (Cι-C4)Haloalkoxy, (Cι-C4)Alkylthio, (Cι-C4)Haloalkylthio, Mono(CrC4)alkylamino, Di(Cι-C4)alkylamino, (C3-C9)Cycloalkyl, [(C-ι-C4)Alkyl]carbonyl, [(C1-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(Cι-C4)alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl und (Cι-C )Haloalkylsulfonyl substituiert ist, und Reste der Formeln R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N-C(=Z,)-I R'-Z-C(=Z')-O-, R'R"N-C(=Z')-Z-, R,-Z-C(=Z,)-NR"- und R'R"N-C(=Z,)-NR,"-) worin R', R" und R,M jeweils unabhängig voneinander Wasserstoff oder bevorzugt (Cι-C4)Alkyl, Phenyl, Phenyl-(Cι-C )alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(Cι-C4)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Cyano, Thiocyanato, (Cι-C4)Alkoxy, (C-ι-C4)Alkylthio, Mono(Cι-C4)alkylamino, Di(CrC4)alkylamino, (C -C4)Alkenyl, (C2-C )Alkinyl, (C3-C6)Cycloalkyl und im Fall cyclischer Reste auch (CrC4)Alkyl und (C-ι-C4)Haloalkyl substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist und inklusive Substituenten vorzugsweise 1 bis 20 C-Atome, insbesondere 1 bis 15 C-Atome aufweist,(C 3 -C 6 ) Cycloalkyl, which is unsubstituted or or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (-C-C 4 ) alkyl, (CrC 4 ) haloalkyl, (CrC 4 ) alkoxy , (CrC 4 ) haloalkoxy, (-C-C 4 ) alkylthio, (CC 4 ) haloalkylthio, mono (CrC 4 ) alkylamino and di (CrC 4 ) alkylamino is substituted, and phenyl and heterocyclyl, each of the latter two radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (Cι-C 4 ) alkyl, (CC) haloalkyl, (CrC 4 ) alkoxy, (Cι-C 4 ) Haloalkoxy, (Cι-C 4 ) alkylthio, (Cι-C 4 ) haloalkylthio, mono (CrC 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C-ι- C 4 ) alkyl] carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino-carbonyl, di (Cι-C 4 ) alkylamino-carbonyl, (Cι-C 4 ) alkylsulfonyl and (-C-C) haloalkylsulfonyl is substituted, and radicals of the formulas R'-C (= Z ') -, R'-C (= Z') - Z-, R'-ZC (= Z ') -, R 'R "NC (= Z , ) - I R'-ZC (= Z') - O-, R'R" NC (= Z ') - Z-, R , -ZC (= Z , ) -NR " - and R'R "NC (= Z , ) -NR , " - ) wherein R ', R "and R , M each independently of one another hydrogen or preferably (-C-C 4 ) alkyl, phenyl, phenyl- (-C-C ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (-C-C 4 ) alkyl, each of the 5 last-mentioned radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino , Nitro, formyl, cyano, thiocyanato, (-C-C 4 ) alkoxy, (C-ι-C 4 ) alkylthio, mono (Cι-C 4 ) alkylamino, di (CrC 4 ) alkylamino, (C -C 4 ) alkenyl , (C 2 -C) alkynyl, (C 3 -C 6 ) cycloalkyl and in the case of cyclic radicals also (CrC 4 ) alkyl and (C-ι-C 4 ) haloalkyl is substituted, and in which Z and Z 'independently of one another are each an oxygen or sulfur atom, is substituted and including substituents preferably 1 to 20 C atoms, in particular 1 to 15 C. -Atoms,
R1 ist weiter bevorzugtR 1 is more preferred
(CrC )Alkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (C1-C4)AIkoxy, (C C4)Alkylthio, (Cι-C4)Alkylsulfonyl und (C3-Cg)Cycloalkyl, das unsubstituiert oder substituiert ist, und Phenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der(CrC) alkyl, which is unsubstituted or by one or more radicals from the group halogen, (C 1 -C 4 ) alkoxy, (CC 4 ) alkylthio, (Cι-C 4 ) alkylsulfonyl and (C 3 -Cg) cycloalkyl, the is unsubstituted or substituted, and phenyl which is unsubstituted or by one or more radicals from the
Gruppe Halogen, (Cι-C4)Alkyl und (C C4)Haloalkyl, (Cι-C4)Alkoxy, (C C4)Haloalkoxy, (d-C4)Alkylthio, Amino, Mono- und Di[(C C4)alkyl]amino, (C1-C4)Alkanoylamino, Benzoylamino, Nitro, Cyano, [(Cι-C )Alkyl]carbonyl, Formyl, Carbamoyl, Mono- und Di-[(d- C )alkyl]aminocarbonyl und (Cι-C4)Alkylsulfonyl substituiert ist, und Heterocyclyl mit 3 bis 6 Ringatomen und 1 bis 3 Heteroringatomen aus der Gruppe N, O und S, wobei der Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Cι-C )Alkyl und Oxo substituiert ist, substituiert ist, oderHalogen group, (-CC 4 ) alkyl and (CC 4 ) haloalkyl, (-C-C 4 ) alkoxy, (CC 4 ) haloalkoxy, (dC 4 ) alkylthio, amino, mono- and di [(CC 4 ) alkyl] amino, (C 1 -C 4 ) alkanoylamino, benzoylamino, nitro, cyano, [(Cι-C) alkyl] carbonyl, formyl, carbamoyl, mono- and di - [(d- C) alkyl] aminocarbonyl and (Cι-C 4 ) Alkylsulfonyl is substituted, and heterocyclyl with 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group N, O and S, the ring being unsubstituted or by one or more radicals from the group halogen, (-C-C) alkyl and oxo is substituted, is substituted, or
Phenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (CrC4)Alkyl, (Cι-C4)Haloalkyl, (Cι-C4)Alkoxy, (C1-C4)Haloalkoxy, (C C4)Alkylthio, (C1-C4)Haloalkylthio, Mono(Cι-C )alkylamino, Di(CrC )alkylamino, (C3-C9)Cycloalkyl, [(CrC4)Alkyl]carbonyl, [(CrC )Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(C1-C4)alkylamino-carbonyl, (Cι-C )Alkylsulfonyl und (C C4)Haloalkylsulfonyl substituiert ist und inklusive Substituenten 2 bis 30 C-Atome, vorzugsweise 2 bis 20 C-Atome, insbesondere 2 bis 15 C-Atome aufweist.Phenyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (CrC 4 ) alkyl, (Cι-C 4 ) haloalkyl, (Cι-C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (CC 4 ) alkylthio, (C 1 -C 4 ) haloalkylthio, mono (Cι-C) alkylamino, di (CrC) alkylamino, (C 3 -C 9 ) cycloalkyl, [(CrC 4 ) alkyl] carbonyl, [(CrC) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino-carbonyl, di (C 1 -C 4 ) alkylamino-carbonyl, (Cι-C) alkylsulfonyl and (CC 4 ) Haloalkylsulfonyl is substituted and including substituents has 2 to 30 C atoms, preferably 2 to 20 C atoms, in particular 2 to 15 C atoms.
R1 ist weiter bevorzugt (CrC4)Alkyl, (Cι-C4)Haloalkyl, Benzyl oder [(C3- C6)Cycloalkyl]-(C1-C2)alkyl, insbesondere (C1-C4)Alkyl, (Cι-C4)Haloalkyl oder [(C3- C6)Cycloalkyl]-methyl, ganz besonders -CH3, -CH2F, -CHF2, -CF3, -CH2CI, -CHCI2, -CCI3, -CH2Br, -CHBr2, -CH2CH3, -CH2CH2F, -CF2CHF2, -CH2CH2CI, -CHFCH3, -CHFCH2CH3, -CH2CH2Br, -CH(CH3)2) -CF(CH3)2, -C(CH3)2CI, -CH2CH2CH2F, -CH2CH2CH2CI oder Cyclopropylmethyl oder 1-Fluor-cycloprop-1-yl.R 1 is further preferred (CrC 4 ) alkyl, (-C-C 4 ) haloalkyl, benzyl or [(C 3 - C 6 ) cycloalkyl] - (C 1 -C 2 ) alkyl, in particular (C 1 -C 4 ) alkyl , (-CC 4 ) haloalkyl or [(C 3 - C 6 ) cycloalkyl] methyl, very particularly -CH 3 , -CH 2 F, -CHF 2 , -CF 3 , -CH 2 CI, -CHCI 2 , -CCI 3 , -CH 2 Br, -CHBr 2 , -CH 2 CH 3 , -CH 2 CH 2 F, -CF 2 CHF 2 , -CH 2 CH 2 CI, -CHFCH 3 , -CHFCH 2 CH 3 , - CH 2 CH 2 Br, -CH (CH 3 ) 2) -CF (CH 3 ) 2 , -C (CH 3 ) 2 CI, -CH 2 CH 2 CH 2 F, -CH 2 CH 2 CH 2 CI or cyclopropylmethyl or 1-fluoro-cycloprop-1-yl.
Bevorzugt sind auch erfindungsgemäße Verbindungen (I), worin R1 Aryl, das unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise 6 bis 30 C-Atome aufweist, oder (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise 3 bis 30 C-Atome aufweist, oder Heterocyclyl, das substituiert oder unsubstituiert ist und inklusive Substituenten vorzugsweise 2 bis 30 C-Atome aufweist, oder (C C6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (Cι-C4)Alkoxy, (CrC4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C )Haloalkenyloxy, (Cι-C4)Alkylthio, (C C4)Alkylsulfinyl, (C C4)Alkylsulfonyl, (C1-C4)Haloalkylsulfinyl, (C1-C4)Haloalkylsulfonyl, (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, und Reste der Formeln R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-, R,R"N-C(=Z')-> R'-Z-C(=Z')-O-, R'R,,N-C(=Z,)-Z-,Also preferred are compounds (I) according to the invention in which R 1 is aryl which is unsubstituted or substituted and preferably contains 6 to 30 C atoms including substituents, or (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted and including substituents preferably Has 3 to 30 C atoms, or heterocyclyl which is substituted or unsubstituted and preferably contains 2 to 30 C atoms including substituents, or (CC 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) Alkynyl, each of the last 3 radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, nitro, thiocyanato, (-C-C 4 ) alkoxy, (CrC 4 ) haloalkoxy, (C 2 -C 4 ) Alkenyloxy, (C 2 -C) haloalkenyloxy, (Cι-C 4 ) alkylthio, (CC 4 ) alkylsulfinyl, (CC 4 ) alkylsulfonyl, (C 1 -C 4 ) haloalkylsulfinyl, (C 1 -C 4 ) haloalkylsulfonyl, (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, heterocyclyl, which is unsubstituted or substituted, and radicals of the formulas R'-C (= Z ') -, R'-C (= Z') - Z-, R'-ZC (= Z ') -, R , R "NC (= Z') - > R'-ZC (= Z ') - O-, R'R ,, NC (= Z , ) -Z- .
R'-Z-C(=Z,)-NR"- und R'R"N-C(=Z,)-NR,"-1 worin R', R" und R'" jeweils unabhängig voneinander (Cι-C6)Alkyl, Aryl,R'-ZC (= Z , ) -NR "- and R'R" NC (= Z , ) -NR , "- 1 wherein R ', R" and R'"each independently of one another (-C-C 6 ) alkyl Aryl
Aryl-(Cι-C6)alkyl, (C3-C9)Cycioalkyl oder (C3-C9)Cycloalkyl-(CrC6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils einAryl- (-C-C 6 ) alkyl, (C 3 -C 9 ) cycioalkyl or (C 3 -C 9 ) cycloalkyl- (CrC 6 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, and in which Z and Z 'independently of one another
Sauerstoff- oder Schwefelatom sind, substituiert ist und inklusive Substituenten vorzugsweise 1 bis 30 C-Are oxygen or sulfur, substituted and preferably including 1 to 30 C-, including substituents
Atome aufweist,Has atoms,
R1 ist vorzugsweise auch Phenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (C1-C4)Alkyl, (Cι-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy, (C C4)Alkylthio, (C C4)Haloalkylthio, Mono(Cι-C )alkylamino, Di(Cι-C4)alkylamino, (C3-C9)Cycloalkyl, [(Cι-C )Alkyl]carbonyl, [(C1-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C )alkylamino-carbonyl, Di(CrC4)alkylamino-carbonyl, (C -C4)Alkylsulfonyl und (Cι-C4)Haloalkylsulfonyl substituiert ist und inklusive Substituenten 6 bis 30 C-Atome, vorzugsweise 6 bis 20 C-Atome, insbesondere 6 bis 15 C-Atome aufweist.R 1 is preferably also phenyl, which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (C 1 -C 4 ) alkyl, (-C-C 4 ) Haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (CC 4 ) alkylthio, (CC 4 ) haloalkylthio, mono (Cι-C) alkylamino, di (Cι-C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(Cι-C) alkyl] carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C) alkylamino-carbonyl, di (CrC 4 ) alkylamino carbonyl, (C -C 4 ) alkylsulfonyl and (-C-C 4 ) haloalkylsulfonyl is substituted and includes 6 to 30 C atoms, preferably 6 to 20 C atoms, in particular 6 to 15 C atoms, including substituents.
Unabhängig von den Resten R1, R3, R4, L°, A1, A2 und (X)n und vorzugsweise in Kombination mit bevorzugten Bedeutungen von einem oder mehreren dieser Reste sind folgende Bedeutungen von R2 von besonderem Interesse:Regardless of the radicals R 1 , R 3 , R 4 , L °, A 1 , A 2 and (X) n and preferably in combination with preferred meanings of one or more of these radicals, the following meanings of R 2 are of particular interest:
R2 ist vorzugsweise (C3-Cg)Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe der Reste A), B), C) und D) substituiert ist, wobei Gruppe A) aus den Resten Halogen, Hydroxy, Amino, Nitro, Formyl,R 2 is preferably (C 3 -Cg) cycloalkyl which is unsubstituted or substituted by one or more radicals from the group of the radicals A), B), C) and D), where group A) from the radicals halogen, hydroxy, Amino, nitro, formyl,
Carboxy, Aminocarbonyl, Sulfo, Cyano, Thiocyanato und Oxo besteht, Gruppe B) aus den Resten (C C6)Alkyl, (CrC6)Alkoxy, (Cι-C6)Alkylthio, Mono(C1-C6)alkylamino, Di(Cι-C4)alkylamino, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C3-C9)Cycloalkyl, (C4-C9)Cycloalkenyl, (CrCeJAlkyliden, (C -C9)Cycloalkyliden, Resten der Formeln R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z'K R,R,,N-C(=Z')-, R,-Z-C(=Z')-O-, R'R"N-C(=Z')-Z-, R'-Z-C(=Z')-NR"- und R,R"N-C(=Z,)-NR'"-, worin R", R" und R'" jeweils unabhängig voneinander Wasserstoff oder besonders (Cι-C6)Alkyl, Phenyl, Phenyl-(C C6)alkyl, (C3-C9)Cycloalkyl oder (C3-C9)Cycloalkyl-(C1-C6)alkyl bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, besteht, Gruppe C) aus Resten gemäß Gruppe B) besteht, wobei jedoch jeder Rest durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (Cι-C4)Alkoxy, (CrC4)Haloalkoxy, (Cι-C4)Alkylthio, (C1-C4)Haloalkylthio, Mono(Cι-C )alkylamino, Di(Cι-C4)alkylamino, (C3-C9)Cycloalkyl, (C4-C9)Cycloalkylen, (C4-C9)Cycloalkyliden, [(Cι-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(CrC )alkylamino-carbonyl, Phenyl, Phenoxy, Phenylthio, Phenylcarbonyl, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio und Heterocyciylamino, wobei jeder der letztgenannten 21 Reste unsubstituiert ist oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Cyano, (C-ι-C4)Alkoxy, (Cι-C4)Alkylthio, (CrC4)Haloalkoxy, Formyl, (C C4)Alkyl-carbonyl und (C-ι-C4)Alkoxy-carbonyl und im Falle von cyclischen Resten auch (C C4)Alkyl, (Cι-C )Haloalkyl und (CrC6)Alkyliden substituiert ist, und im Falle von cyclischen Resten auch (Cι-C6)Alkyl, (Cι-C6)Haloalkyl und (C1-C6)Alkyliden substituiert ist, und Gruppe D) aus divalenten oder trivalenten aliphatischen Brücken mit 1 bis 6, vorzugsweise 1 bis 4 C-Atomen, besteht, die im Fall von divalenten Brücken zwei bzw. im Fall von trivalenten Brücken drei C-Atome des cyclischen Grundkörpers verbinden und der Rest R2 dadurch den Rest eines Bicyclus bzw. Tricyclus darstellt, wobei jeder der Brücken unsubstituiert oder durch einen oder mehrere Substituenten aus der Gruppe Halogen, Nitro, Cyano, (Cι-C4)Alkyl, (CrC4)Alkoxy, (Cι-C4)Alkylthio, (Cι-C4)Haloalkyl, (C1-C4)Haloalkoxy, Formyl, (Cι-C4)Alkyl- carbonyl, (CrC4)Alkoxy-carbonyl und Oxo substituiert ist, und wobei R2 inklusive Substituenten vorzugsweise 3 bis 20 C-Atome, insbesondere 3 bis 15 C-Atome aufweist. Als (C3-Cg)Cycloalkyl-reste sind dabei Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl bevorzugt, insbesondere Cyclopropyl, Cyclobutyl oder Cyclopentyl.Carboxy, aminocarbonyl, sulfo, cyano, thiocyanato and oxo, Group B) from the radicals (CC 6 ) alkyl, (CrC 6 ) alkoxy, (Cι-C 6 ) alkylthio, mono (C 1 -C 6 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 3 -C 9 ) cycloalkyl, (C 4 -C 9 ) cycloalkenyl, (CrCeJ alkylidene, (C -C 9 ) cycloalkylidene, residues of the formulas R'-C ( = Z ') -, R'-C (= Z') - Z-, R'-ZC (= Z'K R , R ,, NC (= Z ') -, R , -ZC (= Z') -O-, R'R "NC (= Z ') - Z-, R'-ZC (= Z') - NR" - and R , R "NC (= Z , ) -NR '" -, where R ", R" and R '"each independently of one another hydrogen or especially (-C-C 6 ) alkyl, phenyl, phenyl- (CC 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 -C 9 ) cycloalkyl- (C 1 -C 6 ) alkyl and in which Z and Z 'are each independently an oxygen or sulfur atom, group C) consists of radicals from group B), but each radical by one or more radicals from the group Halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (-C-C 4 ) alkoxy, (CrC 4 ) haloalkoxy, (Cι-C 4 ) alkylthio, (C 1 -C 4 ) haloalkylthio, mono (Cι-C) alkylamino, di (C 1 -C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, (C 4 -C 9 ) cycloalkylene, (C 4 -C 9 ) cycloalkylidene, [(Cι-C 4 ) alkyl] carbonyl, [ (Cι-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino-carbonyl, di (CrC) alkylamino-carbonyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyciylamino, each of which the latter 21 radicals is unsubstituted or by one or more radicals from the group halogen, nitro, cyano, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (CrC 4 ) haloalkoxy, formyl, (CC 4 ) Alkyl-carbonyl and (C-ι-C 4 ) alkoxy-carbonyl and in the case of cyclic radicals also (CC 4 ) alkyl, (Cι-C) haloalkyl and (CrC 6 ) alkylidene is substituted, and also in the case of cyclic radicals (-C-C 6 ) alkyl, (-C-C 6 ) haloalkyl and (C 1 -C 6 ) alkylidene is substituted, and Group D) consists of divalent or trivalent aliphatic bridges with 1 to 6, preferably 1 to 4, carbon atoms, which in the case of divalent bridges or, in the case of trivalent bridges, three C atoms of the basic cyclic body and the rest R 2 thereby represents the remainder of a bicyclus or tricyclus, each of the bridges being unsubstituted or by one or more substituents from the group halogen, nitro, cyano, (C 1 -C 4 ) alkyl, (CrC 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (Cι-C4) haloalkyl, (C 1 -C 4) haloalkoxy, formyl, (Cι-C 4) alkyl carbonyl, (CrC 4) alkoxy-carbonyl and oxo, and wherein R 2, including substituents, preferably has 3 to 20 carbon atoms, in particular 3 to 15 carbon atoms. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl are preferred as (C 3 -Cg) cycloalkyl radicals, in particular cyclopropyl, cyclobutyl or cyclopentyl.
R2 ist vorzugsweise auch (C4-C8)Cycloalkenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe der Reste A), B), C) und D) substituiert ist, wie sie als Reste für den Fall R2 = (C3-C9)Cycloalkyl definiert sind, und weist dabei inklusive Substituenten vorzugsweise 4 bis 20 C-Atome, insbesondere 4 bis 15 C-Atome auf.R 2 is preferably also (C 4 -C 8 ) cycloalkenyl which is unsubstituted or substituted by one or more radicals from the group consisting of radicals A), B), C) and D), as is the case for radicals R 2 = (C 3 -C 9 ) cycloalkyl are defined, and in this case, including substituents, preferably has 4 to 20 C atoms, in particular 4 to 15 C atoms.
Als (C4-C9)Cycloalkenyl-reste sind dabei 1-CycIobutenyl, 2-Cyclobutenyl, 1- Cyclopentenyl, 2-Cyclopentenyl und 3-Cyclopentenyl bevorzugt.Preferred (C 4 -C 9 ) cycloalkenyl radicals are 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl and 3-cyclopentenyl.
R2 ist vorzugsweise auch Heterocyclyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe der Reste A), B), C) und D) substituiert ist, wie sie als Reste für den Fall R2 = (C3-C9)Cycloalkyl definiert sind.R 2 is preferably also heterocyclyl which is unsubstituted or substituted by one or more radicals from the group consisting of radicals A), B), C) and D), as is the case for radicals R 2 = (C 3 -C 9 ) Cycloalkyl are defined.
Heterocyclyl ist dabei vorzugsweise ein heterocyclischer Rest mit 3 bis 6 Ringatomen und einem Heteroringatom, insbesondere ein Rest aus der Gruppe Pyridyl, Thienyl, Furyl, Pyrrolyl, Oxiranyl, 2-Oxetanyl, 3-Oxetanyl, Oxolanyl (= Tetrahydrofuryl), Pyrrolidyl, Piperidyl, insbesondere Oxiranyl, 2- Oxetanyl, 3-Oxetanyl oder Oxolanyl, oder ist ein heterocyclischer Rest mit zwei oder drei Heteroatomen, beispielsweise Pyrimidinyl, Pyridazinyl, Pyrazinyl, Triazinyl, Thienyl, Thiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Pyrazolyl, Triazolyl, Piperazinyl, Dioxolanyl, Oxazolinyl, Isoxazolinyl, Oxazolidinyl, Isoxazolidinyl oder Morpholinyl.Heterocyclyl is preferably a heterocyclic radical with 3 to 6 ring atoms and a hetero ring atom, in particular a radical from the group pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, 2-oxetanyl, 3-oxetanyl, oxolanyl (= tetrahydrofuryl), pyrrolidyl, piperidyl, in particular oxiranyl, 2-oxetanyl, 3-oxetanyl or oxolanyl, or is a heterocyclic radical with two or three heteroatoms, for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl or isoxazinylinyl.
R2 ist vorzugsweise auch Phenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe der Reste A), B) und C) substituiert ist, wie sie als Reste für R2 = (C3-Cg)Cycloalkyl definiert sind.R 2 is preferably also phenyl which is unsubstituted or substituted by one or more radicals from the group consisting of radicals A), B) and C), as defined as radicals for R 2 = (C 3 -Cg) cycloalkyl.
R2 weist inklusive Substituenten vorzugsweise bis 20 C-Atome, insbesondere bis 15 C-Atome, ganz besonders bis 10 C-Atome auf.R 2 , including substituents, preferably has up to 20 C atoms, in particular up to 15 C atoms, very particularly up to 10 C atoms.
R2 ist bevorzugt (C3-C9)Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe der Reste A), B), C) und D) substituiert ist, wobeiR 2 is preferably (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted by one or more radicals from the group consisting of radicals A), B), C) and D), where
Gruppe A) aus den Resten Halogen, Hydroxy, Nitro, Formyl, Aminocarbonyl, Cyano und Thiocyanato besteht,Group A) consists of the radicals halogen, hydroxy, nitro, formyl, aminocarbonyl, cyano and thiocyanato,
Gruppe B) aus den Resten (Cι-C4)Alkyl, (C1-C4)Alkoxy, (C C4)Alkylthio, Mono(Cι-C )alkylamino, Di(Cι-C4)alkyiamino, (C2-C4)AIkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl, (C4-C6)Cycloalkenyl, (Cι-C4)Alkyliden, (C4-C6)Cycloalkyliden, Resten der Formeln R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z,)-) R'R"N-C(=Z')-, R,-Z-C(=Z')-O-, R'R"N-C(=Z,)-Z-, R'-Z-C(=Z,)-NR"- und R,R"N-C(=Z')-NR,"-J worin R', R" und R'" jeweils unabhängig voneinander Wasserstoff oder insbesondere (Cι-C4)Alkyl, Phenyl, Phenyl- (Cι-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(Cτ Cβ)alkyl bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, besteht,Group B) from the residues (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (CC 4 ) alkylthio, mono (Cι-C) alkylamino, di (Cι-C 4 ) alkyiamino, (C 2 - C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 4 -C 6 ) cycloalkenyl, (Cι-C 4 ) alkylidene, (C 4 -C 6 ) cycloalkylidene, residues of the formulas R'-C (= Z ') -, R'-C (= Z') - Z-, R'-ZC (= Z , ) - ) R'R "NC (= Z ') -, R , -ZC (= Z ') - O-, R'R "NC (= Z , ) -Z-, R'-ZC (= Z , ) -NR" - and R , R "NC (= Z') -NR , "- J wherein R ', R" and R'"each independently of one another hydrogen or in particular (-C-C 4 ) alkyl, phenyl, phenyl- (C-C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (Cτ Cβ) alkyl and where Z and Z 'are each independently an oxygen or sulfur atom,
Gruppe C) aus Resten gemäß Gruppe B) besteht, wobei jedoch jeder Rest durch einen oder mehrere Reste aus der Gruppe Halogen, (C C4)Alkoxy, (Cι-C4)Haloalkoxy, (C C4)Alkylthio, (Cι-C4)Haloalkylthio, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (C3-C6)Cycloalkyl, [(C C )Alkyl]carbonyl, [(Ci -C4)AI koxyjcarbonyl , Aminocarbonyl , Mono(Cι-C4)alkylamino-carbonyl, Di(Cι-C4)alkylamino-carbonyl, Phenyl, Phenoxy, Phenylthio, Phenylcarbonyl, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio und Heterocyciylamino, wobei jeder der letztgenannten 8 Reste unsubstituiert ist oder einen oder mehrere Substituenten aus der Gruppe Halogen, Nitro, Cyano, (C C4)Alkyl, (Cι-C4)Alkoxy, (C C4)Alkylthio, (C1-C4)Haloalkyl, (C C4)Haloalkoxy, (Cι-C4)Alkyl-carbonyl und (CrC4)Alkoxy-carbonyl aufweist, substituiert ist, und Gruppe D) aus divalenten aliphatischen Brücken besteht, die zwei C-Atome des cyclischen Grundkörpers verbinden und dadurch der Rest R2 den Rest eines Bicyclus darstellt, beispielsweise Bicyclo[1.1.0]butan-1-yl, Bicyclo[1.1.0]butan-2-yl, Bicyclo[2.1.0]pentan-1-yl, Bicyclo[2.1.0]pentan-2-yl oder Bicyclo[2.1.0]pentan-5-yl, wobei jeder der Brücken unsubstituiert oder durch einen oder mehrere Substituenten aus der Gruppe Halogen, (C1-C4)Alkyl, (Cι-C4)Alkoxy, (C C4)Alkylthio, (Cι-C4)Haloalkyl, (CrC4)Haloalkoxy, (Cι-C4)Alkyl-carbonyl, (CrC4)Alkoxy-carbonyl und Oxo substituiert ist.Group C) consists of radicals according to group B), but each radical consists of one or more radicals from the group halogen, (CC 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (CC 4 ) alkylthio, (-C-C 4 ) haloalkylthio, mono (Cι-C 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 3 -C 6 ) cycloalkyl, [(CC) alkyl] carbonyl, [(Ci -C 4 ) AI koxyjcarbonyl, aminocarbonyl, mono (-C-C 4 ) alkylamino-carbonyl, di (Cι-C 4 ) alkylamino-carbonyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyciylaminote, each of the latter 8 unsubstituted or one or more substituents from the group halogen, nitro, cyano, (CC 4) alkyl, (Cι-C 4) alkoxy, (CC 4) alkylthio, (C 1 -C 4) haloalkyl, (CC 4) haloalkoxy, (-C-C 4 ) alkyl-carbonyl and (CrC 4 ) alkoxy-carbonyl, is substituted, and group D) consists of divalent aliphatic bridges that connect two carbon atoms of the basic cyclic body and thereby the radical R 2 the rest of one Represents bicyclus, for example bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, bicyclo [2.1.0] pentan-2- yl or bicyclo [2.1.0] pentan-5-yl, where each of the Bridges unsubstituted or by one or more substituents from the group halogen, (C 1 -C 4 ) alkyl, (Cι-C 4 ) alkoxy, (CC 4 ) alkylthio, (Cι-C 4 ) haloalkyl, (CrC 4 ) haloalkoxy, (-C-C 4 ) alkyl-carbonyl, (CrC 4 ) alkoxy-carbonyl and oxo is substituted.
ist besonders bevorzugt (C3-C9)Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Thiocyanato, (C-ι-C4)Alkyl, (Cι-C4)Haloalkyl, (Cι-C4)Alkoxy, (C C4)Haloalkoxy, (CrC4)Alkylthio, (Cι-C4)Haloalkylthio, (CrC4)Alkyliden, Mono(Cι-C4)alkylamino und Di(CrC4)alkylamino substituiert ist, oder Heterocyclyl oder Phenyl, wobei jeder der letztgenannten beiden Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (C C )Alkyl, (CrC4)Haloalkyl, (C C4)Alkoxy, (C1-C4)Haloalkoxy, (C1-C4)Alkylthio, (Cι-C4)Haloalkylthio, Mono(Cι-C )alkylamino, Di(Cι-C4)alkylamino, (C3-C6)Cycloalkyl, Heterocyclyl mit 3 bis 6 Ringatomen, [(Cι-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(CrC4)alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl und (Cι-C4)Haloalkylsulfonyl substituiert ist.is particularly preferred (C 3 -C 9 ) cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, thiocyanato, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, ( C 1 -C 4 ) alkoxy, (CC 4 ) haloalkoxy, (CrC 4 ) alkylthio, (Cι-C 4 ) haloalkylthio, (C r C 4 ) alkylidene, mono (Cι-C 4 ) alkylamino and di (CrC 4 ) alkylamino or heterocyclyl or phenyl, each of the latter two radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (CC) alkyl, (CrC 4 ) haloalkyl, (CC 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (Cι-C 4 ) haloalkylthio, mono (Cι-C) alkylamino , Di (C 1 -C 4 ) alkylamino, (C 3 -C 6 ) cycloalkyl, heterocyclyl having 3 to 6 ring atoms, [(C 1 -C 4 ) alkyl] carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl, aminocarbonyl, Mono (-C-C 4 ) alkylamino-carbonyl, di (CrC 4 ) alkylamino-carbonyl, (Cι-C 4 ) alkylsulfonyl and (Cι-C 4 ) haloalkylsulfonyl is substituted.
Unabhängig von den Resten R1, R2, R4 , A1, A2, L° und (X)n und vorzugsweise in Kombination mit bevorzugten Bedeutungen von einem oder mehreren dieser Reste sind folgende Bedeutungen von R3 von besonderem Interesse:Regardless of the radicals R 1 , R 2 , R 4 , A 1 , A 2 , L ° and (X) n and preferably in combination with preferred meanings of one or more of these radicals, the following meanings of R 3 are of particular interest:
wobei die Reste R bis R )17 weiter unten definiert sind. where the radicals R to R) 17 are defined below.
Von besonderem Interesse sind auch Verbindungen, bei denenAlso of particular interest are connections where
R6 und R7 gemeinsam mit dem Stickstoffatom der Gruppe NR6R7,R 6 and R 7 together with the nitrogen atom of group NR 6 R 7 ,
R7 und OR8 gemeinsam mit dem Stickstoffatom der Gruppe NOR8R7,R 7 and OR 8 together with the nitrogen atom of the group NOR 8 R 7 ,
R7 und SR8 gemeinsam mit dem Stickstoffatom der Gruppe NSR8R7,R 7 and SR 8 together with the nitrogen atom of the group NSR 8 R 7 ,
R10 und R1 gemeinsam mit dem Stickstoffatom der Gruppe NR10R11,R 10 and R 1 together with the nitrogen atom of group NR 10 R 11 ,
OR12 und OR13 bzw. SR12 und SR13 gemeinsam mit dem Kohlenstoffatom derOR 12 and OR 13 or SR 12 and SR 13 together with the carbon atom of the
Gruppen der FormelnGroups of formulas
OR9 und R14 bzw. SR9 und R14 gemeinsam mit dem Kohlenstoffatom der GruppenOR 9 and R 14 or SR 9 and R 14 together with the carbon atom of the groups
R14 und R15 gemeinsam mit dem Kohlenstoffatom der Gruppe R5 und R7 gemeinsam mit der AtomgruppierungR 14 and R 15 together with the carbon atom of the group R 5 and R 7 together with the atom grouping
H dαerr Gϊrriuinppceinn H dαerr Gϊrriuinppceinn
R und R »17 gemeinsam mit dem Kohlenstoffatom der GruppeR and R »17 together with the carbon atom of the group
R und R »16 gemeinsam mit der AtomgruppeR and R »16 together with the atomic group
R16 der Gruppe R16 of the group
R7 und R10 gemeinsam mit der AtomgruppierungR 7 and R 10 together with the atom grouping
der Gruppe the group
jeweils unabhängig voneinander einen carbocyclischen bzw. heterocyclischen Ring mit 3 bis 7 Ringatomen und 1 bis 6 Heteroatomen, wobei die gegebenenfalls weiteren Heteroringatome aus der Gruppe N, O und S ausgewählt sind und der carbocyclische oder heterocyclische Ring jeweils unsubstituiert oder substituiert ist, bilden, wobei die Reste R5 bis R17 nachstehend definiert sind. each independently form a carbocyclic or heterocyclic ring having 3 to 7 ring atoms and 1 to 6 heteroatoms, where the further hetero ring atoms, if appropriate, are selected from the group consisting of N, O and S and the carbocyclic or heterocyclic ring is in each case unsubstituted or substituted, where the radicals R 5 to R 17 are defined below.
In den vorstehenden Formeln für Atomgruppierungen deutet das Symbol für eine Doppelbindung "=", die nur an einer Seite Substituenten aufweist (einseitig gebundene Doppelbindung), die Bindungsstelle einer Doppelbindung an (= eine freie Doppelbindung, gleichbedeutend mit der Bindungsstelle eines Ylidenrestes) und nicht die Kurzschreibweise für Vinyl.In the above formulas for atomic groupings, the symbol for a double bond "=", which has substituents on only one side (single-bonded double bond), indicates the binding site of a double bond (= a free double bond, equivalent to the binding site of a ylidene radical) and not that Abbreviation for vinyl.
R5, R6, R7, R8, R9, R10, R11, R14, R15, R16, R17 in den vorstehenden Formeln sind unabhängig voneinanderR 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 in the above formulas are independent of one another
Wasserstoff, Aryl, das unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise 6 bis 30 C-Atome aufweist, oder (C3- C9)Cycloaikyl, das unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise 3 bis 30 C-Atome aufweist, oder Heterocyclyl, das substituiert oder unsubstituiert ist und inklusive Substituenten vorzugsweise 2 bis 30 C-Atome aufweist, oder (C1-C6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (CrC4)Alkoxy, (Cι-C )Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (C C4)Alkylthio, (Cι-C4)Alkylsulfinyl, (Cι-C4)Alkylsulfonyl, (C1-C4)Haloalkylsulfinyl, (C C4)Haloalkylsulfonyl, (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, und Reste der Formeln R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N-C(=Z')-, R'-Z-C(=Z')-O-, R,R"N-C(=Z')-Z-, R'-Z-C(=Z')-NR"- und R,R"N-C(=Z,)-NR,"-> worin R', R" und R'" jeweils unabhängig voneinander Wasserstoff oder besonders (Cι-C6)Alkyl, Aryl, Aryl-(CrC6)aIkyl, (C3-C9)Cycloalkyl oder (C3-C9)Cycloalkyl-(Cι-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist und inklusive Substituenten vorzugsweise 1 bis 30 C- Atome aufweist.Hydrogen, aryl which is unsubstituted or substituted and preferably has 6 to 30 C atoms including substituents, or (C 3 - C 9 ) cycloaikyl which is unsubstituted or substituted and preferably has 3 to 30 C atoms including substituents, or heterocyclyl , which is substituted or unsubstituted and including substituents preferably has 2 to 30 carbon atoms, or (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 residues unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, nitro, thiocyanato, (CrC 4 ) alkoxy, (Cι-C) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) Haloalkenyloxy, (CC 4 ) alkylthio, (-C-C 4 ) alkylsulfinyl, (Cι-C 4 ) alkylsulfonyl, (C 1 -C 4 ) haloalkylsulfinyl, (CC 4 ) haloalkylsulfonyl, (C 3 -C 9 ) cycloalkyl, that is unsubstituted or substituted, phenyl which is unsubstituted or substituted, heterocyclyl which is unsubstituted or substituted, and the rest e of the formulas R'-C (= Z ') -, R'-C (= Z') - Z-, R'-ZC (= Z ') -, R'R "NC (= Z') -, R'-ZC (= Z ') - O-, R , R "NC (= Z') - Z-, R'-ZC (= Z ') - NR" - and R , R "NC (= Z , ) -NR , "- > wherein R ', R "and R'" are each independently hydrogen or particularly (Cι-C6) alkyl, aryl, aryl (CrC 6) -alkyl, (C 3 -C 9) cycloalkyl or (C 3 -C 9) Cycloalkyl- (-C-C 6 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, and where Z and Z 'are each independently an oxygen or sulfur atom, is substituted and, including substituents, preferably 1 to 30 C atoms having.
R12, R13 sind jeweils unabhängig voneinanderR 12 , R 13 are each independent of one another
Aryl, das unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise 6 bis 30 C-Atome aufweist, oder (C3-Cg)Cycloalkyl, das unsubstituiert oder substituiert ist und inklusive Substituenten vorzugsweise 3 bis 30 C-Atome aufweist, oder Heterocyclyl, das substituiert oder unsubstituiert ist und inklusive Substituenten vorzugsweise 2 bis 30 C-Atome aufweist, oder (C-i-CeJAlkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (CrC4)Alkoxy, (d-C )Haloalkoxy, (C2-C )Alkenyloxy, (C2-C4)Haloalkenyloxy, (C-ι-C4)Alkylthio, (C C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (CrC4)Haloalkylsulfinyl, (CrO Haloalkylsulfonyl, (C3-Cg)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, und Reste der Formeln R'-C(=Z')-, R,-C(=Z')-Z-, R,-Z-C(=Z')-, R'R"N-C(=Z')-, R'-Z-C(=Z')-O-, R'R"N-C(=Z')-Z-, R'-Z-C(=Z')-NR"- und R'R,,N-C(=Z,)-NR,"-J worin R', R" und R"' jeweils unabhängig voneinander Wasserstoff oder besonders (C1-C6)Alkyl, Aryl, Aryl-(CrC6)alkyl, (C3-C9)Cycloalkyl oder (C3-Cg)Cycloalkyl-(CrC6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist und inklusive Substituenten vorzugsweise 1 bis 30 C-Aryl which is unsubstituted or substituted and preferably has 6 to 30 C atoms including substituents, or (C 3 -Cg) cycloalkyl which is unsubstituted or substituted and preferably has 3 to 30 C atoms including substituents, or heterocyclyl which substitutes or is unsubstituted and, including substituents, preferably has 2 to 30 C atoms, or (Ci-CeJalkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 radicals being unsubstituted or by one or several residues from the group halogen, hydroxy, cyano, nitro, thiocyanato, (CrC 4 ) alkoxy, (dC) haloalkoxy, (C 2 -C) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (C-ι-C 4 ) Alkylthio, (CC 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, (CrC 4 ) haloalkylsulfinyl, (CrO haloalkylsulfonyl, (C 3 -Cg) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, Heterocyclyl, which is unsubstituted or substituted, and radicals of the formulas R'-C (= Z ') -, R , -C (= Z ') - Z-, R , -ZC (= Z') -, R'R "NC (= Z ') -, R'-ZC (= Z') - O-, R'R "NC (= Z ') - Z-, R'-ZC (= Z') - NR" - and R'R ,, NC (= Z , ) -NR , "- J where R ', R" and R "'each independently of one another hydrogen or especially (C 1 -C 6 ) alkyl, aryl, aryl- (CrC 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 -Cg) cycloalkyl- (CrC 6 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, and in which Z and Z ' are each independently an oxygen or sulfur atom, is substituted and, including substituents, preferably 1 to 30 C -
Atome aufweist.Has atoms.
Vorzugsweise bedeuten die Reste R5, R6, R7, R8, R9, R10, R11, R14, R15, R16, R17 jeweils unabhängig voneinander Wasserstoff.The radicals R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 each independently represent hydrogen.
Vorzugsweise bedeuten die Reste R5, R6, R7, R8, R9, R10, R11, R14, R15, R16, R17 jeweils unabhängig voneinander auchThe radicals R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 are each also independently of one another
Phenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (d-C4)Alkyl, (d-C4)Haloalkyl, (d-C4)Alkoxy, (Cι-C4)Haloalkoxy, (d-d)Alkylthio, (Cι-C )Haloalkylthio, Mono(d-C )alkylamino, Di(Cι-C4)alkylamino, (C3-Cg)Cycloalkyl, [(Cι-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(Cι-C )alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl und (CrC )Haloalkylsulfonyl substituiert ist und inklusive Substituenten 6 bis 30 C- Atome, vorzugsweise 6 bis 20 C-Atome, insbesondere 6 bis 5 C-Atome aufweist.Phenyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (dC 4 ) alkyl, (dC 4 ) haloalkyl, (dC 4 ) alkoxy, ( -C-C 4 ) haloalkoxy, (dd) alkylthio, (Cι-C) haloalkylthio, mono (dC) alkylamino, di (Cι-C 4 ) alkylamino, (C 3 -Cg) cycloalkyl, [(Cι-C 4 ) alkyl ] carbonyl, [(-C-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino-carbonyl, di (Cι-C) alkylamino-carbonyl, (Cι-C 4 ) alkylsulfonyl and (CrC) haloalkylsulfonyl substituted and includes substituents 6 to 30 C atoms, preferably 6 to 20 C atoms, in particular 6 to 5 C atoms.
Vorzugsweise bedeuten die Reste R5, R6, R7, R8, R9, R10, R11, R14, R15, R16, R17 jeweils unabhängig voneinander auchThe radicals R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 are each also independently of one another
(C3-C9)Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Thiocyanato, (Cι-C4)Alkyl, (d-C4)Haloalkyl, (Cι-C4)Alkoxy, (d-C4)Haloalkoxy, (d-C4)Alkylthio, (CrC4)Haloalkylthio, Mono(d-C4)alkylamino und Di(d-C4)alkylamino substituiert ist und inklusive Substituenten 3 bis 30 C-Atome, vorzugsweise 3 bis 20 C-Atome, insbesondere 3 bis 15 C-Atome aufweist.(C 3 -C 9 ) cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (C 1 -C 4 ) alkyl, (dC 4 ) haloalkyl, (C 1 -C 4 ) Alkoxy, (dC 4 ) haloalkoxy, (dC 4 ) alkylthio, (CrC 4 ) haloalkylthio, mono (dC 4 ) alkylamino and di (dC 4 ) alkylamino is substituted and including substituents 3 to 30 C atoms, preferably 3 to 20 C -Atoms, in particular 3 to 15 carbon atoms.
Vorzugsweise bedeuten die Reste R5, R6, R7, R8, R9, R10, R11, R14, R15, R16, R17 jeweils unabhängig voneinander auchThe radicals R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 are each also independently of one another
Heterocyclyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (d-C4)Alkyl, (C C4)Haloalkyl, (C C4)Alkoxy, (C1-C )Haloalkoxy, (d-C4)Alkylthio, (d-C^Haloalkylthio, Mono(Cι-C4)alkylamino, Di(d-C4)alkylamino, (C3-C9)Cycloalkyl, [(C -C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(Cι-C )alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl und (Cι-C )Haloalkylsulfonyl substituiert ist und inklusive Substituenten 2 bis 30 C- Atome, vorzugsweise 2 bis 20 C-Atome, insbesondere 2 bis 15 C-Atome aufweist.Heterocyclyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, Thiocyanato, (dC 4 ) alkyl, (CC 4 ) haloalkyl, (CC 4 ) alkoxy, (C 1 -C) haloalkoxy, (dC 4 ) alkylthio, (dC ^ haloalkylthio, mono (Cι-C 4 ) alkylamino, di ( dC 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C -C 4 ) alkyl] carbonyl, [(Cι-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino-carbonyl, di (-C-C) alkylamino-carbonyl, (-C-C 4 ) alkylsulfonyl and (Cι-C) haloalkylsulfonyl is substituted and including substituents 2 to 30 C atoms, preferably 2 to 20 C atoms, in particular 2 to 15 C atoms having.
Dabei und auch in anderen Resten ist Heterocyclyl vorzugsweise ein heterocyclischer Rest mit 3 bis 7, insbesondere 3 bis 6 Ringatomen und einem Heteroatom aus der Gruppe N, O und S, beispielsweise Pyridyl, Thienyl, Furyl, Pyrrolyl, Oxiranyl, Oxetanyl, Oxolanyl (= Tetrahydrofuryl), Oxanyl, Pyrrolidyl, Piperidyl, oder ist ein heterocyclischer Rest mit zwei oder drei Heteroatomen aus der Gruppe Pyrimidinyl, Pyridazinyl, Pyrazinyl, Triazinyl, Thienyl, Thiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Pyrazolyl, Triazolyl, Piperazinyl, Dioxolanyl, Oxazolinyl, Isoxazolinyl, Oxazolidinyl, Isoxazolidinyl, Morpholinyl.Here and also in other radicals, heterocyclyl is preferably a heterocyclic radical with 3 to 7, in particular 3 to 6 ring atoms and a heteroatom from the group N, O and S, for example pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, oxetanyl, oxolanyl (= Tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl, or is a heterocyclic radical with two or three heteroatoms from the group pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl Isoxazolinyl, oxazolidinyl, isoxazolidinyl, morpholinyl.
R5, R6, R7, R8, R9, R10, R11, R14, R15, R16, R17 sind jeweils unabhängig voneinander vorzugsweise auch (CrC6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (Cι-C4)Alkoxy, (d- C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (C C4)Alkylthio, (C C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl, (CrC )Haloalkylsulfonyl, (C3-C6)Cycloalkyl, das unsubstituiert oder oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Thiocyanato, (d-C4)Alkyl, (d-C4)Haloalkyl, (d-C4)Alkoxy, (d-C4)Haloalkoxy, (C C4)Alkylthio, (d-C4)Haloalkylthio, Mono(Cι-C4)alkylamino und Di(Cι-C4)alkylamino substituiert ist, Phenyl und Heterocyclyl, wobei jeder der zwei letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (d-C4)Alkyl, (d-C4)Haioalkyl, (d-C4)Alkoxy, (d-C4)Haloalkoxy, (C1-C )Alkylthio, (C C4)Haloalkylthio, Mono(Cι-C4)alkylamino, Di(d-C )alkylamino, (C3-C9)Cycloalkyl, [(d-C )Alkyl]carbonyl, [(CrC4)Alkoxy]carbonyl, Aminocarbonyl, Mono(d-C )alkylamino-carbonyl, Di(C C4)alkylamino-carbonyl, (d-C4)Alkylsulfonyl und (Cι-C4)Haloalkylsulfonyl substituiert ist, und Reste der Formeln R'-C(=Z , R'- C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N-C(=Z')-, R'-Z-C(=Z')-O-, R'R"N-C(=Z')-Z-, R'-Z-C(=Z')- NR"- und R'R"N-C(=Z')-NR'"-, worin R', R" und R'" jeweils unabhängig voneinander Wasserstoff oder besonders (d-C4)Alkyl, Phenyl, Phenyl-(C1-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(Cι-C )alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Cyano, Thiocyanato, (d-C4)Alkoxy, (Cι-C4)Alkylthio, Mono(C1-C4)alkylamino, Di(d-C4)alkylamino, (C2-C4)Alkenyl, (C2-C )Alkinyl, (C3-C6)Cycloalkyl und im Fall cyclischer Reste auch (d- C4)Alkyl und (d-C4)Haloalkyl substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist und inklusive Substituenten vorzugsweise 1 bis 20 C-Atome, insbesondere 1 bis 15 C-Atome aufweist,R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 are each, independently of one another, preferably also (CrC 6 ) alkyl, (C 2 -C 6 ) Alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, nitro, thiocyanato, (C 1 -C 4 ) alkoxy, (d- C 4 ) Haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (CC 4 ) alkylthio, (CC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl, (CrC) haloalkylsulfonyl , (C 3 -C 6 ) cycloalkyl which is unsubstituted or or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (dC 4 ) alkyl, (dC 4 ) haloalkyl, (dC 4 ) alkoxy, (dC 4 ) haloalkoxy, (CC 4 ) alkylthio, (dC 4 ) haloalkylthio, mono (-C-C 4 ) alkylamino and di (Cι-C 4 ) alkylamino is substituted, phenyl and heterocyclyl, each of the latter two radicals being unsubstituted or by one or more radicals from the group halogen, hyd roxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (dC 4 ) alkyl, (dC 4 ) haioalkyl, (dC 4 ) alkoxy, (dC 4 ) haloalkoxy, (C 1 -C) alkylthio, (CC 4 ) haloalkylthio, mono (-C 4 ) alkylamino, di (dC) alkylamino, (C 3 -C 9 ) cycloalkyl, [(dC) alkyl] carbonyl, [(CrC 4 ) alkoxy] carbonyl, aminocarbonyl, Mono (dC) alkylamino-carbonyl, di (CC 4 ) alkylamino-carbonyl, (dC 4 ) alkylsulfonyl and (Cι-C 4 ) haloalkylsulfonyl is substituted, and radicals of the formulas R'-C (= Z, R'- C ( = Z ') - Z-, R'-ZC (= Z') -, R'R "NC (= Z ') -, R'-ZC (= Z') - O-, R'R" NC ( = Z ') - Z-, R'-ZC (= Z') - NR "- and R'R" NC (= Z ') - NR'"-, where R ', R" and R'"are each independent one another is hydrogen or especially (dC 4 ) alkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (Cι-C) alkyl, each the 5 last-mentioned radicals is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, cyano, thiocyanato, (dC 4) alkoxy, (Cι-C 4) alkylthio, mono (C 1 -C 4) alkylamino, di (dC 4 ) alkylamino, (C 2 -C 4 ) alkenyl, (C 2 -C) alkynyl, (C 3 -C 6 ) cycloalkyl and in the case of cyclic radicals also (d- C 4 ) alkyl and (dC 4 ) Haloalkyl is substituted, and where Z and Z 'are each independently an oxygen or sulfur atom, is substituted and including Subst ituents preferably has 1 to 20 C atoms, in particular 1 to 15 C atoms,
R5, R6, R7, R8, R9, R10, R11, R14, R15, R16, R17 sind jeweils unabhängig voneinander bevorzugt (Cι-C4)Alkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (d-C4)Alkoxy, (C1-C4)Alkylthio, (d-C4)Alkylsulfonyl, (C3- Cg)Cycloalkyl, das unsubstituiert oder substituiert ist, und Phenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Cι-C4)Alkyl und (d-C4)Haloalkyl, (d-C4)Alkoxy, (C1-C )Haloalkoxy, (Cι-C4)AIkylthio, Amino, Mono- und Di[(Cι-C4)alkyl]amino, (Cι-C4)Alkanoylamino, Benzoylamino, Nitro, Cyano, [(d- C4)Alkyl]carbonyl, Formyl, Carbamoyl, Mono- und Di-[(Cι-C )alkyl]aminocarbonyl und (CrC )Alkylsulfonyl substituiert ist, und Heterocyclyl mit 3 bis 6 Ringatomen und 1 bis 3 Heteroringatomen aus der Gruppe N, O und S, wobei der Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Cι-C4)Alkyl und Oxo substituiert ist, substituiert ist, oder Phenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (d-C4)Alkyl, (Cι-C4)Haloalkyl, (d-C4)Alkoxy, (Cι-C4)Haloalkoxy, (Cι-C )Alkylthio, (C1-C4)Haloalkylthio, Mono(Cι-C )alkylamino, Di(Cι-C )alkylamino, (C3-Cg)Cycloalkyl, [(d-C4)Alkyl]carbonyl, [(Cι-C )Alkoxy]carbonyl, Aminocarbonyl, Mono(d-C4)alkylamino-carbonyl, Di(Cι-C4)alkylamino-carbonyl, (d-C4)Alkylsulfonyl und (d-C4)Haloalkylsulfonyl substituiert ist und inklusive Substituenten 2 bis 30 C- Atome, vorzugsweise 2 bis 20 C-Atome, insbesondere 2 bis 15 C-atome aufweist.R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 are each independently preferred (-C-C 4 ) alkyl which is unsubstituted or by one or more radicals from the group consisting of halogen, (dC 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (dC 4 ) alkylsulfonyl, (C 3 - Cg) cycloalkyl which is unsubstituted or substituted, and phenyl which is unsubstituted or substituted by one or more radicals from the group halogen, (-CC 4 ) alkyl and (dC 4 ) haloalkyl, (dC 4 ) alkoxy, (C 1 -C) haloalkoxy, (-C-C 4 ) alkylthio, amino, mono- and Di [(-C-C 4 ) alkyl] amino, (Cι-C 4 ) alkanoylamino, benzoylamino, nitro, cyano, [(d- C 4 ) alkyl] carbonyl, formyl, carbamoyl, mono- and di - [(Cι- C) alkyl] aminocarbonyl and (CrC) alkylsulfonyl, and heterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group N, O and S, the ring being unsubstituted or by one or more radicals from the group halogen, ( Cι-C 4 ) alkyl and oxo is substituted, is substituted, or Ph enyl, which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (dC 4 ) alkyl, (Cι-C 4 ) haloalkyl, (dC 4 ) alkoxy , (-C-C 4 ) haloalkoxy, (Cι-C) alkylthio, (C 1 -C 4 ) haloalkylthio, mono (Cι-C) alkylamino, di (Cι-C) alkylamino, (C 3 -Cg) cycloalkyl, [(dC 4 ) alkyl] carbonyl, [(-C-C) alkoxy] carbonyl, aminocarbonyl, mono (dC 4 ) alkylamino-carbonyl, di (Cι-C 4 ) alkylamino-carbonyl, (dC 4 ) alkylsulfonyl and (dC 4 ) Haloalkylsulfonyl is substituted and including substituents has 2 to 30 C atoms, preferably 2 to 20 C atoms, in particular 2 to 15 C atoms.
R12, R13 sind jeweils unabhängig voneinander vorzugsweise auch Phenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (CrC4)Alkyl, (Cι-C4)Haloalkyl, (d-C4)Alkoxy, (C1-C4)Haloalkoxy, (d-C4)Alkylthio, (Cι-C4)Haloalkylthio, Mono(d-C4)alkylamino, Di(d-C )alkylamino, (C3-C9)Cycloalkyl, [(CrC4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(Cι-C4)alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl und (CrC4)Haloalkylsulfonyl substituiert ist und inklusive Substituenten 6 bis 30 C- Atome, vorzugsweise 6 bis 20 C-Atome, insbesondere 6 bis 15 C-Atome aufweist.R 12 , R 13 are each independently, preferably also phenyl, which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (CrC 4 ) alkyl, (Cι -C 4 ) haloalkyl, (dC 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (dC 4 ) alkylthio, (Cι-C 4 ) haloalkylthio, mono (dC 4 ) alkylamino, di (dC) alkylamino, (C 3 -C 9 ) cycloalkyl, [(CrC 4 ) alkyl] carbonyl, [(-C-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino-carbonyl, di (Cι-C 4 ) alkylamino-carbonyl , (-C-C 4 ) alkylsulfonyl and (CrC 4 ) haloalkylsulfonyl is substituted and includes 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, in particular 6 to 15 carbon atoms, including substituents.
R12, R 3 sind jeweils unabhängig voneinander vorzugsweise auch (C3-C9)Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Thiocyanato, (Cι-C )Alkyl, (Cι-C )Haloalkyl, (Cι-C4)Alkoxy, (d-C4)Haloalkoxy, (d-C4)Alkylthio, (d-C4)Haloalkylthio, Mono(Cι-C4)alkylamino und Di(Cι-C4)alkylamino substituiert ist und inklusive Substituenten 3 bis 30 C- Atome, vorzugsweise 3 bis 20 C-Atome, insbesondere 3 bis 15 C-Atome aufweist.R 12 , R 3 are each independently of one another preferably also (C 3 -C 9 ) cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (-C-C) alkyl, (-C. -C) Haloalkyl, (-C-C 4 ) alkoxy, (dC 4 ) haloalkoxy, (dC 4 ) alkylthio, (dC 4 ) haloalkylthio, mono (Cι-C 4 ) alkylamino and di (Cι-C 4 ) alkylamino is substituted and including substituents having 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, in particular 3 to 15 carbon atoms.
R12, R13 sind jeweils unabhängig voneinander vorzugsweise auch Heterocyclyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (Cι-C )Alkyl, (d-C4)Haloalkyl, (d-C4)Alkoxy, (Cι-C4)Haloalkoxy, (C C4)Alkylthio, (Cι-C )Haloalkylthio, Mono(d-C4)alkylamino, Di(Cι-C4)alkylamino, (C3-C9)Cycloalkyl, [(Cι-C4)Alkyl]carbonyl, [(d-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(CrC4)alkylamino-carbonyl, Di(Cι-C )alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl und (CrC4)Haloalkylsulfonyl substituiert ist und inklusive Substituenten 2 bis 30 C- Atome, vorzugsweise 2 bis 20 C-Atome, insbesondere 2 bis 15 C-Atome aufweist. Dabei und auch in anderen Resten ist Heterocyclyl vorzugsweise ein heterocyclischer Rest mit 3 bis 7, insbesondere 3 bis 6 Ringatomen und einem Heteroatom aus der Gruppe N, O und S, beispielsweise Pyridyl, Thienyl, Furyl, Pyrrolyl, Oxiranyl, Oxetanyl, Oxolanyl (= Tetrahydrofuryl), Oxanyl, Pyrrolidyl, Piperidyl, oder ist ein heterocyclischer Rest mit zwei oder drei Heteroatomen aus der Gruppe Pyrimidinyl, Pyridazinyl, Pyrazinyl, Triazinyl, Thienyl, Thiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Pyrazolyl, Triazolyl, Piperazinyl, Dioxolanyl, Oxazolinyl, Isoxazolinyl, Oxazolidinyl, Isoxazolidinyl, Morpholinyl.R 12 , R 13 are each, independently of one another, preferably also heterocyclyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (C 1 -C 8) alkyl, ( dC 4 ) haloalkyl, (dC 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (CC 4 ) alkylthio, (Cι-C) haloalkylthio, mono (dC 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(-C-C 4 ) alkyl] carbonyl, [(dC 4 ) alkoxy] carbonyl, aminocarbonyl, mono (CrC 4 ) alkylamino-carbonyl, di (Cι-C) alkylamino-carbonyl, (Cι -C 4 ) alkylsulfonyl and (CrC 4 ) haloalkylsulfonyl is substituted and including substituents has 2 to 30 C atoms, preferably 2 to 20 C atoms, in particular 2 to 15 C atoms. Here and also in other radicals, heterocyclyl is preferably a heterocyclic radical with 3 to 7, in particular 3 to 6 ring atoms and a heteroatom from the group N, O and S, for example pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, oxetanyl, oxolanyl (= Tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl, or is a heterocyclic radical with two or three heteroatoms from the group pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl, triazolyl Isoxazolinyl, oxazolidinyl, isoxazolidinyl, morpholinyl.
R12, R13 sind jeweils unabhängig voneinander vorzugsweise auch (Cι-C6)Alkyl, (C2-Ce) Alkenyl oder (C2-C6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (Cι-C4)Alkoxy, (Cι-C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (C C4)Alkylthio, (C1-C4)Alkylsulfinyl, (d- C4)Alkylsulfonyl, (Cι-C )Haloalkylsulfinyl, (Cι-C )Haloalkylsulfonyl, (C3-C6)Cycloalkyl, das unsubstituiert oder oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Thiocyanato, (CrC4)Alkyl, (Cι-C )Haloalkyl, (d-C4)Alkoxy, (d-C4)Haloa!koxy, (d-C4)Alkylthio, (C1-C4)Haloalkylthio, Mono(Ct-C4)alkylamino und Di(Cι-C )alkylamino substituiert ist, Phenyl und Heterocyclyl, wobei jeder der zwei letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (d-C4)Alkyl, (Cι-C )Haloalkyl, (d-C4)Alkoxy, (d-C4)Haloalkoxy, (C C4)Alkylthio, (d-C4)Haloalkylthio, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (C3-C9)Cycloalkyl, [(C C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(C C4)alkylamino-carbonyl, (Cι-C )Alkylsulfonyl und (Cι-C4)Haloalkylsulfonyl substituiert ist, und Reste der Formeln R'-C(=Z , R'- C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N-C(=Z')-, R'-Z-C(=Z')-O-, R'R"N-C(=Z')-Z-, R'-Z-C(=Z')-NR"- und R'R"N-C(=Z')-NR'"-, worin R', R" und R'" jeweils unabhängig voneinander Wasserstoff oder besonders (d-C4)Alkyl, Phenyl, Phenyl-(C C4)alkyl, (C3-C6)Cycloalkyl oder (C3-Ce)Cycloalkyl-(CrC )alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Cyano, Thiocyanato, (d-C4)Alkoxy, (CrC4)Alkylthio, Mono(C1-C4)alkylamino, Di(C1-C4)alkylamino, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl und im Fall cyclischer Reste auch (d- C4)Alkyl und (CrC )Haloalkyl substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist und inklusive Substituenten vorzugsweise 1 bis 20 C-Atome, insbesondere 1 bis 15 C-Atome aufweist.R 12 , R 13 are each, independently of one another, preferably also (-C 6 ) alkyl, (C 2 -Ce) alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 residues being unsubstituted or by one or more residues the group halogen, hydroxy, cyano, nitro, thiocyanato, (Cι-C 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (CC 4 ) Alkylthio, (C 1 -C 4 ) alkylsulfinyl, (d- C 4 ) alkylsulfonyl, (Cι-C) haloalkylsulfinyl, (Cι-C) haloalkylsulfonyl, (C 3 -C 6 ) cycloalkyl, which is unsubstituted or or by one or more Radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (CrC 4 ) alkyl, (Cι-C) haloalkyl, (dC 4 ) alkoxy, (dC 4 ) haloakoxy, (dC 4 ) alkylthio, (C 1 -C 4 ) haloalkylthio, mono (C t -C 4 ) alkylamino and di (Cι-C) alkylamino is substituted, phenyl and heterocyclyl, each of the latter two radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, Amino, nitro, formyl, carboxy, sulfo nyl, cyano, thiocyanato, (dC 4 ) alkyl, (Cι-C) haloalkyl, (dC 4 ) alkoxy, (dC 4 ) haloalkoxy, (CC 4 ) alkylthio, (dC 4 ) haloalkylthio, mono (Cι-C 4 ) alkylamino, di (-C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(CC 4 ) alkyl] carbonyl, [(Cι-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino -carbonyl, di (CC 4 ) alkylamino-carbonyl, (Cι-C) alkylsulfonyl and (Cι-C 4 ) haloalkylsulfonyl is substituted, and radicals of the formulas R'-C (= Z, R'- C (= Z ') -Z-, R'-ZC (= Z ') -, R'R "NC (= Z') -, R'-ZC (= Z ') - O-, R'R" NC (= Z') -Z-, R'-ZC (= Z ') - NR "- and R'R" NC (= Z') - NR '"-, wherein R', R" and R '"each independently of one another are hydrogen or especially (dC 4 ) alkyl, phenyl, phenyl- (CC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C e ) cycloalkyl- (CrC) alkyl, each of the 5 latter radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, cyano, thiocyanato, (dC 4 ) alkoxy, (CrC 4 ) alkylthio, mono (C 1 -C 4 ) alkylamino, di (C 1 -C 4 ) alkylamino, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl and in the case of cyclic radicals also (d- C 4 ) alkyl and (CrC) haloalkyl is substituted, and where Z and Z 'are each independently an oxygen or sulfur atom, are substituted and, including substituents, preferably have 1 to 20 C atoms, in particular 1 to 15 C atoms.
R12, R13 sind jeweils unabhängig voneinander bevorzugt (Cι-C4)Alkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (d-C4)Alkoxy, (d-C4)Alkylthio, (d-C4)Alkylsulfonyl, (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist, und Phenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Cι-C )Alkyl und (d-C )Haloalkyl, (d-C4)Alkoxy, (C C )Haloalkoxy, (C C4)Alkylthio, Amino, Mono- und Di[(C C4)alkyl]amino, (C -C4)Alkanoylamino, Benzoylamino, Nitro, Cyano, [(Ci- C4)Alkyl]carbonyl, Formyl, Carbamoyl, Mono- und Di-[(Cι-C4)alkyl]aminocarbonyl und (Cι-C )Alkylsulfonyl substituiert ist, und Heterocyclyl mit 3 bis 6 Ringatomen und 1 bis 3 Heteroringatomen aus der Gruppe N, O und S, wobei der Ring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (d-C4)Alkyl und Oxo substituiert ist, substituiert ist, oder Phenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (Cι-C )Alkyl, (Cι-C4)Haloalkyi, (d-C4)Alkoxy, (d-C4)Haloalkoxy, (C C4)Alkylthio, (d-C4)Haloalkylthio, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (C3-C9)Cycloalkyl, [(Cι-C4)Alkyl]carbonyl, [(d-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(Cι-C4)alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl und (Cι-C4)Haloalkylsulfonyl substituiert ist und inklusive Substituenten 2 bis 30 C- Atome, vorzugsweise 2 bis 20 C-Atome, insbesondere 2 bis 15 C-atome aufweist. Unabhängig von den Resten R1, R2, R3, L°, A1, A2 und (X)n und vorzugsweise in Kombination mit bevorzugten Bedeutungen von einem oder mehreren dieser Reste sind folgende Bedeutungen von R4 von besonderem Interesse:R 12 , R 13 are each independently preferred (-CC 4 ) alkyl which is unsubstituted or by one or more radicals from the group halogen, (dC 4 ) alkoxy, (dC 4 ) alkylthio, (dC 4 ) alkylsulfonyl, ( C 3 -C 9 ) Cycloalkyl, which is unsubstituted or substituted, and phenyl, which is unsubstituted or by one or more radicals from the group halogen, (-C-C) alkyl and (dC) haloalkyl, (dC 4 ) alkoxy, (CC ) Haloalkoxy, (CC 4 ) alkylthio, amino, mono- and di [(CC 4 ) alkyl] amino, (C -C 4 ) alkanoylamino, benzoylamino, nitro, cyano, [(Ci-C 4 ) alkyl] carbonyl, formyl , Carbamoyl, mono- and di - [(-C-C 4 ) alkyl] aminocarbonyl and (Cι-C) alkylsulfonyl is substituted, and heterocyclyl with 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group N, O and S, where the ring is unsubstituted or substituted by one or more radicals from the group halogen, (dC 4 ) alkyl and oxo, or phenyl which is unsubstituted or by one or more radicals from the group e halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (Cι-C) alkyl, (Cι-C 4 ) haloalkyi, (dC 4 ) alkoxy, (dC 4 ) haloalkoxy, (CC 4 ) Alkylthio, (dC 4 ) haloalkylthio, mono (-C-C 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(Cι-C 4 ) alkyl] carbonyl, [(dC 4 ) Alkoxy] carbonyl, aminocarbonyl, mono (-C-C 4 ) alkylamino-carbonyl, di (Cι-C 4 ) alkylamino-carbonyl, (Cι-C 4 ) alkylsulfonyl and (Cι-C 4 ) haloalkylsulfonyl is substituted and includes substituents 2 has up to 30 carbon atoms, preferably 2 to 20 carbon atoms, in particular 2 to 15 carbon atoms. Regardless of the radicals R 1 , R 2 , R 3 , L °, A 1 , A 2 and (X) n and preferably in combination with preferred meanings of one or more of these radicals, the following meanings of R 4 are of particular interest:
R4 bedeutet beispielsweise einen Rest der Formel -B1-D1, wobei B1 und D1 vorzugsweise wie weiter unten definiert sind.R 4 means, for example, a radical of the formula -B 1 -D 1 , where B 1 and D 1 are preferably as defined below.
R4 ist vorzugsweise Wasserstoff, (C1-C )Alkyl, Phenyl oder (C3-C6)Cycloalkyl, wobei jeder der 3 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (Cι-C4)Alkoxy, (Cι-C4)Haloalkoxy, (d-C4)Alkylthio, (Cι-C4)Haloalkylthio, Mono(d-C4)alkylamino, Di(d-C )alkylamino, (C3-C9)Cycloalkyl, [(C1-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(d-C4)aIkylamino-carbonyl, Di(CrC4)alkylamino-carbonyl, (d-C4)Alkylsulfonyl, (Cι-C )Haloalkylsulfonyl und im Fall cyclischer Reste auch (Cι-C4)Alkyl und (CrC4)Haloalkyl substituiert ist, oderR 4 is preferably hydrogen, (C 1 -C) alkyl, phenyl or (C 3 -C 6 ) cycloalkyl, each of the 3 last-mentioned radicals being unsubstituted or by one or more radicals from the group consisting of halogen, hydroxy, amino, nitro, formyl , Carboxy, sulfonyl, cyano, thiocyanato, (Cι-C 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (dC 4 ) alkylthio, (Cι-C 4 ) haloalkylthio, mono (dC 4 ) alkylamino, di (dC) alkylamino, (C 3 -C 9 ) cycloalkyl, [(C 1 -C 4 ) alkyl] carbonyl, [(Cι-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (dC 4 ) aIkylamino-carbonyl, di (CrC 4 ) alkylamino-carbonyl, (dC 4 ) alkylsulfonyl, (Cι-C) haloalkylsulfonyl and in the case of cyclic radicals also (Cι-C 4 ) alkyl and (CrC 4 ) haloalkyl is substituted, or
Formyl, [(d-C )Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl oder Di(Cι-C4)alkylamino-carbonyl; insbesondere Wasserstoff, Methyl, Ethyl, n-Propyl oder Isopropyl; ganz bevorzugt Wasserstoff.Formyl, [(dC) alkyl] carbonyl, [(-C-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino-carbonyl or di (Cι-C 4 ) alkylamino-carbonyl; in particular hydrogen, methyl, ethyl, n-propyl or isopropyl; most preferably hydrogen.
Unabhängig von den Resten R1 bis R4, A1, A2 und (X)n und vorzugsweise in Kombination mit bevorzugten Bedeutungen von einem oder mehreren dieser Reste sind folgende Bedeutungen von L° von besonderem Interesse: L° ist eine direkte Bindung oder Sauerstoff.Regardless of the radicals R 1 to R 4 , A 1 , A 2 and (X) n and preferably in combination with preferred meanings of one or more of these radicals, the following meanings of L ° are of particular interest: L ° is a direct bond or Oxygen.
Unabhängig von den Resten R1 bis R4, L°, A2 und (X)n und vorzugsweise in Kombination mit bevorzugten Bedeutungen von einem oder mehreren dieser Reste sind folgende Bedeutungen von A1 von besonderem Interesse: A1 bedeutet beispielsweise geradkettiges Alkylen mit 1 bis 5 C-Atomen oder geradkettiges Alkenylen oder Alkinylen mit jeweils 2 bis 5 C-Atomen, wobei jeder der drei letztgenannten Diradikale unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Cyano, Thiocyanato und einen Rest der Formel -B2-D2 substituiert ist, worin B2 eine direkte Bindung oder eine divalente Gruppe der Formeln -O-, -SO2-, -CO-, -O-CO-, -NR° -, -NR°-CO-, -CO-NR0-, -O-CO-NR0- oder -NR°-CO-O- bedeutet, in denen die ResteRegardless of the radicals R 1 to R 4 , L °, A 2 and (X) n and preferably in combination with preferred meanings of one or more of these radicals, the following meanings of A 1 are of particular interest: A 1 means, for example, straight-chain alkylene with 1 to 5 C atoms or straight-chain alkenylene or alkynylene each with 2 to 5 C atoms, each of the three last-mentioned diradicals being unsubstituted or by one or more radicals from the group halogen, nitro, cyano, thiocyanato and a radical of the formula -B 2 -D 2 is substituted, in which B 2 is a direct bond or a divalent group of the formulas -O-, -SO 2 -, -CO-, -O-CO-, -NR ° -, -NR ° -CO-, -CO-NR 0 -, -O-CO-NR 0 - or -NR ° -CO-O- means in which the radicals
R° unabhängig voneinander jeweils Wasserstoff, (d-C4)Alkyl, Phenyl, Phenyl-(d-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(C1-C4)alkyl, wobei jeder der letztgenannten 5 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (Cι-C )Alkoxy, (Cι-C4)Haloalkoxy, (CrC4)Alkylthio, (d-C4)Haloalkylthio, Mono(C C )alkylamino, Di(C1-C4)alkylamino, (C3-C9)Cycloalkyl, [(Cι-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyi, Di(C -C )alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl, (CrC4)Haloalkylsulfonyl und im Fall cyclischer Reste auch (Cι-C4)Alkyl und (CrC )Haloalkyl substituiert ist, bedeuten.R ° independently of one another are each hydrogen, (dC 4 ) alkyl, phenyl, phenyl- (dC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (C 1 -C 4 ) alkyl, where each of the last 5 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (Cι-C) alkoxy, (Cι-C 4 ) haloalkoxy, ( CrC 4 ) alkylthio, (dC 4 ) haloalkylthio, mono (CC) alkylamino, di (C 1 -C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(Cι-C 4 ) alkyl] carbonyl, [(Cι -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (-C-C 4 ) alkylamino-carbonyi, di (C -C) alkylamino-carbonyl, (Cι-C 4 ) alkylsulfonyl, (CrC 4 ) haloalkylsulfonyl and in the case of cyclic radicals also (-C-C 4 ) alkyl and (CrC) haloalkyl is substituted.
A1 ist vorzugsweise ein Rest der FormelA 1 is preferably a radical of the formula
-CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2 - oder -CH2CH2CH2CH2CH2-, der unsubstituiert ist. Bevorzugt ist auch einer der vorstehenden Reste, der durch einen oder auch mehrere der genannten Reste -B2-D2 substituiert ist. Besonders bevorzugt ist A1 ein Rest der Formel -CH2CH2- oder -CH2CH2CH2-, der unsubstituiert oder durch einen oder zwei Reste der Formel Hydroxy, (Cι-C4)Alkyl oder (Cι-C )Alkoxy substituiert ist.-CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 - or -CH 2 CH 2 CH 2 CH 2 CH 2 -, which is unsubstituted. Also preferred is one of the above radicals, which is substituted by one or more of the radicals -B 2 -D 2 mentioned . A 1 is particularly preferably a radical of the formula -CH 2 CH 2 - or -CH 2 CH 2 CH 2 - which is unsubstituted or by one or two radicals of the formula hydroxyl, (-CC 4 ) alkyl or (-CC) Alkoxy is substituted.
Unabhängig von den Resten R1 bis R4, L°, A1 und (X)n und vorzugsweise in Kombination mit bevorzugten Bedeutungen von einem oder mehreren dieser Reste sind folgende Bedeutungen von A2 von besonderem Interesse: A2 ist vorzugsweise eine direkte Bindung oder eine Gruppe der Formel -CH2-, -CH2CH2-,Regardless of the radicals R 1 to R 4 , L °, A 1 and (X) n and preferably in combination with preferred meanings of one or more of these radicals, the following meanings of A 2 are of particular interest: A 2 is preferably a direct bond or a group of the formula -CH 2 -, -CH 2 CH 2 -,
-CH2CH2CH2- oder -CH2CH2CH2CH2-, wobei jeder der 4 letztgenannten-CH 2 CH 2 CH 2 - or -CH 2 CH 2 CH 2 CH 2 -, each of the 4 latter
Diradikale unsubstituiert oder durch einen oder mehrere Reste aus derDiradical unsubstituted or by one or more residues from the
Gruppe Halogen, Nitro, Cyano, Thiocyanato und Reste der Formel -B3-D3 substituiert ist, oder ein divalenter Rest der Formel V1, V2, V3, V4 oder V5,Halogen, nitro, cyano, thiocyanato and radicals of the formula -B 3 -D 3 is substituted, or a divalent radical of the formula V 1 , V 2 , V 3 , V 4 or V 5 ,
-CRaRb-W*-CRcRd - (V)-CR a R b -W * -CR c R d - (V)
-CRaRb-W*-CRcRd-CReRf- (V2)-CR a R b -W * -CR c R d -CR e R f - (V 2 )
-CRaRb-CRcRd-W*-CReRf- (V3)-CR a R b -CR c R d -W * -CR e R f - (V 3 )
-CRaRb-CRcRd-W*- (V4)-CR a R b -CR c R d -W * - (V 4 )
-CRaRb-W*- (V5) wobei jeder der Reste Ra bis Rf jeweils unabhängig voneinander Wasserstoff,-CR a R b -W * - (V 5 ) where each of the radicals R a to R f are each independently hydrogen,
Halogen, Nitro, Cyano, Thiocyanato oder einen Rest der Formel -B4-D4 ist,Is halogen, nitro, cyano, thiocyanato or a radical of the formula -B 4 -D 4 ,
W* jeweils O, S oder eine Gruppe der Formel N(B5-D5) ist undW * is in each case O, S or a group of the formula N (B 5 -D 5 ) and
B3, B4, B5, D3, D4 und D5 wie unten definiert sind,B 3 , B 4 , B 5 , D 3 , D 4 and D 5 are as defined below,
A2 ist besonders bevorzugt eine direkte Bindung oder eine Gruppe der Formel -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH , -CH2-O-CH2-, -CH2-O-CH2-CH2-, -CH2-CH2-O-CH2-, -CH -S-CH2-, -CH2-S-CH2-CH2-, -CH2-CH2-S-CH2-, -CH2-NH-CH2-, -CH2-NH-CH2-CH2-, -CH2-CH2-NH-CH2-, -CH2-N(CH3)-CH2-, -CH2-N(CH3)-CH2-CH2- oder -CH2-CH2-N(CH3)-CH2-.A 2 is particularly preferably a direct bond or a group of the formula -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH, -CH2-O-CH 2 -, -CH 2 -O-CH 2 -CH 2 -, -CH 2 -CH 2 -O-CH 2 -, -CH -S-CH 2 -, -CH 2 -S-CH 2 -CH 2 -, -CH 2 -CH 2 -S-CH 2 -, -CH 2 -NH-CH 2 -, -CH 2 -NH-CH 2 -CH 2 -, -CH 2 -CH 2 -NH-CH 2 -, - CH 2 -N (CH 3 ) -CH 2 -, -CH 2 -N (CH 3 ) -CH 2 -CH 2 - or -CH 2 -CH 2 -N (CH 3 ) -CH 2 -.
B1 und B5 sind vorzugsweise jeweils unabhängig voneinander eine direkte Bindung oder eine divalente Gruppe der Formeln -C(=Z*)-, -C(=Z*)-Z**-, -C(=Z*)-NH- oder -C(=Z*)-NR% wobei Z* = O oder S, Z** = O oder S und R* = (d-C )Alkyl, Phenyl, Phenyl-(d-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(CrC4)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, vorzugsweise unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (Cι-C4)Alkoxy, (d-C )Haloalkoxy, (d-C4)Alkylthio, (C1-C4)Haloalkylthio, Mono(d-C4)alkylamino, Di(Cι-C4)alkylamino, (C3-C9)Cycloalkyl, [(d-C4)Alkyl]carbonyl, [(d~C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C )alkylamino-carbonyl, Di(C1-C4)alkylamino-carbonyl, (C C4)Alkylsulfonyl, (CrC4)Haloalkylsulfonyl und im Fall cyclischer Reste auch (Cι-C4)Alkyl und (Crd)Haloalkyl substituiert ist. Weiter bevorzugt sind B1 und B5 unabhängig voneinander eine direkte Bindung oder eine divalente Gruppe der Formeln -C(=Z*)-, -C(=Z*)-Z**-, -C(=Z*)-NH- oder -C(=Z*)-NR*-, wobei Z* = O oder S, Z** = O oder S und R* = (d-C4)Alkyl, Phenyl, Phenyl-(Cι-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(d-C4)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Formyl, (C1-C4)Alkoxy, (d-C4)Haloalkoxy, (Cι-C )Alkylthio, Mono(d-C4)alkylamino, Di(d-C4)alkylamino, (C3-C9)Cycloalkyl, [(C C4)Alkyi]carbonyl, [(C1-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyi, Di(Cι-C4)alkyiamino-carbonyl und im Fall cyclischer Reste auch (Cι-C )Alkyl und (Cι-C4)Haloalkyl substituiert ist, sind, insbesondere R* = (Cι-C4)Alkyl oder (C3- Cδ)Cycloalkyl oder insbesondere R* = Phenyl oder Phenyl-(Cι-C4)alkyl, wobei jeder der beiden letztgenannten Reste im Phenylteil unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Cι-C4)Alkyl, (d-C4)Haloalkyl, (Cι-C4)Alkoxy oder (Cι-C )Haloalkoxy substituiert ist, ist.B 1 and B 5 are preferably each independently a direct bond or a divalent group of the formulas -C (= Z *) -, -C (= Z *) - Z ** -, -C (= Z *) - NH - or -C (= Z *) - NR% where Z * = O or S, Z ** = O or S and R * = (dC) alkyl, phenyl, phenyl- (dC 4 ) alkyl, (C 3 - C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (CrC 4 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, Formyl, carboxy, sulfo, cyano, thiocyanato, (Cι-C 4 ) alkoxy, (dC) haloalkoxy, (dC 4 ) alkylthio, (C 1 -C 4 ) haloalkylthio, mono (dC 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(dC 4 ) alkyl] carbonyl, [(d ~ C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (-C-C) alkylamino-carbonyl, di (C 1 -C 4 ) alkylamino-carbonyl, (CC 4 ) alkylsulfonyl, (CrC 4 ) haloalkylsulfonyl and in the case of cyclic Residues are also substituted (-C 4 ) alkyl and (Crd) haloalkyl. B 1 and B 5 are furthermore, independently of one another, a direct bond or a divalent group of the formulas -C (= Z *) -, -C (= Z *) - Z ** -, -C (= Z *) - NH - or -C (= Z *) - NR * -, where Z * = O or S, Z ** = O or S and R * = (dC 4 ) alkyl, phenyl, phenyl- (-C-C 4 ) alkyl , (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (dC 4 ) alkyl, where each of the 5 last-mentioned residues is unsubstituted or by one or more residues from the group halogen, hydroxy, amino, formyl, ( C 1 -C 4 ) alkoxy, (dC 4 ) haloalkoxy, (-C-C) alkylthio, mono (dC 4 ) alkylamino, di (dC 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(CC 4 ) alkyi ] carbonyl, [(C 1 -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (-C-C 4 ) alkylamino-carbonyi, di (Cι-C 4 ) alkyiamino-carbonyl and in the case of cyclic radicals also (Cι-C) alkyl and (-C-C 4 ) haloalkyl is substituted, in particular R * = (Cι-C 4 ) alkyl or (C 3 - C δ ) cycloalkyl or in particular R * = phenyl or phenyl- (Cι-C 4 ) alkyl, each of the latter two radicals in the phenyl part is unsubstituted or substituted by one or more radicals from the group halogen, (C 1 -C 4 ) alkyl, (dC 4 ) haloalkyl, (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) haloalkoxy.
B2, B3 und B4 sind vorzugsweise jeweils unabhängig voneinander eine direkte Bindung oder eine divalente Gruppe der Formeln -O-, -S(O)p-, -S(O)p-O-, -O -S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR° -, -O-NR0-, -NR°-O-, -NR°-CO-, -CO-NR°-, -O-CO-NR0- oder -NR°-CO-O-, wobei p die ganze Zahl 0, 1 oder 2 ist und R° = Wasserstoff, (d-C4)Alkyl, Phenyl, Phenyl-(d-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(d-C4)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (d-C4)Alkoxy, (Cι-C4)Haloalkoxy, (d-C4)Alkylthio, (Cι-C4)Haloalkylthio, Mono(d-C )alkylamino, Di(Cι-C )alkylamino, (C3-C9)Cycloalkyl, [(CrC4)Alkyl]carbonyl, [(d-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(C1-C4)alkylamino-carbonyl, Di(d-C4)alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl, (Cι-C4)Haloalkylsulfonyl und im Fall cyclischer Reste auch (d-C4)Alkyl und (Cι-C )Haloalkyl substituiert ist, bedeutet und insbesondere R° = Wasserstoff, (C1-C4)Alkyl oder (C3-C6)Cycloalkyl oder insbesondere R° = Phenyl oder Phenyl-(d-C4)alkyl, wobei jeder der beiden letztgenannten Reste im Phenylteil unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Cι-C )Alkyl, (Cι-C4)Haloalkyl, (Cι-C )Alkoxy oder (d-C )Haloalkoxy substituiert ist, ist.B 2 , B 3 and B 4 are preferably each independently a direct bond or a divalent group of the formulas -O-, -S (O) p -, -S (O) p -O-, -O -S (O ) p -, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O -, -NR ° -, -O-NR 0 -, -NR ° -O-, -NR ° -CO-, -CO-NR ° -, -O-CO-NR 0 - or -NR ° -CO- O-, where p is the integer 0, 1 or 2 and R ° = hydrogen, (dC 4 ) alkyl, phenyl, phenyl- (dC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (dC 4 ) alkyl, each of the 5 last-mentioned radicals being unsubstituted or by one or more radicals from the group consisting of halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (dC 4 ) alkoxy, (-C-C 4 ) haloalkoxy, (dC 4 ) alkylthio, (Cι-C 4 ) haloalkylthio, mono (dC) alkylamino, di (Cι-C) alkylamino, (C 3 -C 9 ) cycloalkyl, [(CrC 4 ) Alkyl] carbonyl, [(dC 4 ) alkoxy] carbonyl, aminocarbonyl, mono (C 1 -C 4 ) alkylamino-carbonyl, di (dC 4 ) alkylamino-carbonyl, (Cι-C 4) alkylsulfonyl, (Cι-C4) haloalkylsulfonyl and in the case of cyclic radicals, also (dC 4) alkyl and (Cι-C) haloalkyl is substituted, and in particular R ° = hydrogen, (C 1 -C 4 ) Alkyl or (C 3 -C 6 ) cycloalkyl or in particular R ° = phenyl or phenyl- (dC 4 ) alkyl, where each of the latter two radicals in the phenyl part is unsubstituted or by one or more radicals from the group halogen, (-C-C ) Alkyl, (-C-C 4 ) haloalkyl, (-C-C) alkoxy or (dC) haloalkoxy is substituted.
B2, B3 und B4 sind weiter bevorzugt unabhängig voneinander eine direkte Bindung oder eine divalente Gruppe der Formeln -O-, -S(O)p-, -CO-,B 2 , B 3 and B 4 are more preferably, independently of one another, a direct bond or a divalent group of the formulas -O-, -S (O) p -, -CO-,
-O-CO-, -CO-O-, -S-CO-, -CO-S-, -NR° -, -NR°-CO-, -CO-NR°-, -O-CO-NR°- oder -NR°-CO-O-, wobei p die ganze Zahl 0, 1 oder 2, insbesondere 0 oder 2 ist und R° die genannte Bedeutung hat, ganz besonders H oder (CrC )Alkyl ist.-O-CO-, -CO-O-, -S-CO-, -CO-S-, -NR ° -, -NR ° -CO-, -CO-NR ° -, -O-CO-NR ° - or -NR ° -CO-O-, where p is the integer 0, 1 or 2, in particular 0 or 2 and R ° has the meaning given, very particularly H or (CrC) alkyl.
D1, D2, D3, D4 und D5 bedeuten vorzugsweise unabhängig voneinander Wasserstoff, (d-d Alkyl, Phenyl, Phenyl-(Cι-C4)alkyl, (C3-C6)Cycloalkyl oder (C3- CβJCycloalkyKd-CβJalkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, vorzugsweise unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (d-C )Alkoxy, (Cι-C4)Haloalkoxy, (d-C )Alkylthio, (d-C4)Haloalkylthio, Mono(Cι-C4)alkylamino, Di(d-C4)alkylamino, (C3-Cg)Cycloalkyl, [(C1-C )Alkyl]carbonyl, [(d-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(C1-C4)alkylamino-carbonyl, Di(d-C4)alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl, (Cι-C )Haloalkylsulfonyl und im Fall cyclischer Reste auch (C C )Alkyl und (d-C4)Haloalkyl substituiert ist.D 1 , D 2 , D 3 , D 4 and D 5 preferably independently of one another are hydrogen, (dd alkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 - CβJCycloalkyKd -CβJalkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (dC) alkoxy, (Cι -C 4 ) haloalkoxy, (dC) alkylthio, (dC 4 ) haloalkylthio, mono (Cι-C 4 ) alkylamino, di (dC 4 ) alkylamino, (C 3 -Cg) cycloalkyl, [(C 1 -C) alkyl] carbonyl, [(dC 4 ) alkoxy] carbonyl, aminocarbonyl, mono (C 1 -C 4 ) alkylamino-carbonyl, di (dC 4 ) alkylamino-carbonyl, (Cι-C 4 ) alkylsulfonyl, (Cι-C) haloalkylsulfonyl and im In the case of cyclic radicals also (CC) alkyl and (dC 4 ) haloalkyl is substituted.
Weiter bevorzugt bedeuten D1, D2, D3, D4 und D5 unabhängig voneinander (Cι-C4)Alkyl, Phenyl, Phenyl-(d-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl- (Cι-C4)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Formyl, (d-C )Alkoxy, (Cι-C4)Haloalkoxy, (C C4)Alkylthio, Mono(Cι-C4)alkylamino, Di(C C4)alkylamino, (C3-C9)Cycloalkyl, [(d-C4)Alkyl]carbonyl, [(C -C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(CrC4)alkylamino-carbonyl, Di(CrC4)alkylamino-carbonyl und im Fall cyclischer Reste auch (Cι-C4)Alkyl und (Cι-C4)Haloalkyl substituiert ist, und bedeuten insbesondereD 1 , D 2 , D 3 , D 4 and D 5 are furthermore preferably (C 1 -C 4 ) alkyl, phenyl, phenyl- (dC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 - C 6 ) Cycloalkyl- (-C-C 4 ) alkyl, each of the 5 last-mentioned radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, formyl, (dC) alkoxy, (-C-C 4 ) haloalkoxy, (CC 4 ) alkylthio, mono (Cι-C 4 ) alkylamino, di (CC 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(dC 4 ) alkyl ] carbonyl, [(C -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (CrC 4 ) alkylamino-carbonyl, di (CrC 4 ) alkylamino-carbonyl and in the case of cyclic radicals also (Cι-C 4 ) alkyl and (Cι- C 4 ) Haloalkyl is substituted, and in particular mean
(CrC )Alkyl oder (C3-C6)Cycloalkyl oder Phenyl oder Phenyl-(C C4)alkyl, wobei jeder der beiden letztgenannten Reste im Phenylteil unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (CrC )Alkyl, (Cι-C4)Haloalkyl, (Cι-C4)Alkoxy oder (Cι-C )Haloalkoxy substituiert ist.(CrC) alkyl or (C 3 -C 6 ) cycloalkyl or phenyl or phenyl- (CC 4 ) alkyl, where each of the latter two residues in the phenyl part is unsubstituted or by one or more residues from the group halogen, (CrC) alkyl, ( C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) haloalkoxy is substituted.
Unabhängig von den Resten R1 bis R4, L°, A1 und A2 und vorzugsweise in Kombination mit bevorzugten Bedeutungen von einem oder mehreren dieser Reste sind folgende Bedeutungen von (X)n von besonderem Interesse:Regardless of the radicals R 1 to R 4 , L °, A 1 and A 2 and preferably in combination with preferred meanings of one or more of these radicals, the following meanings of (X) n are of particular interest:
(X)n bedeutet n Substituenten X, wobei die Reste X vorzugsweise jeweils unabhängig voneinander Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Cyano, Thiocyanato, Aminocarbonyl oder (Cι-C )Alkyl, (CrC4)Alkoxy, (Cι-C4)Alkylthio, Mono(d-C4)alkylamino, Di(C C4)alkylamino, (C2-C4)Alkenyl, (C2-C4)Alkinyl, [(d-C4)Alkyl]carbonyl, [(d-C4)Alkoxy]carbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(d-C4)alkylamino-carbonyl, N-(CrC6)Alkanoyl-amino oder N-(Cι-C4)Alkanoyl-N-(Cι-C4)alkyl-amino, wobei jeder der letztgenannten 13 Reste unsubstituiert oder substituiert ist, vorzugsweise unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Thiocyanato, (Cι-C4)Alkoxy, (C1-C4)Haloalkoxy, (C C4)Alkylthio, Mono(d-C4)alkylamino, Di(Cι-C4)alkylamino, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkylamino, [(d-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino- carbonyl, Di(d-C4)alkylamino-carbonyl, Phenyl, Phenoxy, Phenylthio, Phenylcarbonyi, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio und Heterocyciylamino, wobei jeder der letztgenannten 8 Reste unsubstituiert ist oder einen oder mehrere Substituenten aus der Gruppe Halogen, Nitro, Cyano, (d-C4)Alkyl, (d-C4)Alkoxy, (d-C4)Alkylthio, (d-C4)Haloalkyl, (Cι-C )Haloalkoxy, Formyl, (Cι-C )Alkyl-carbonyl und (Cι-C )Alkoxy- carbonyl aufweist, substituiert ist, oder (C3-Cg)Cycloalkyl, Phenyl, Phenoxy, Phenylthio, Phenylcarbonyl, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio oder Heterocyciylamino, wobei jeder der letztgenannten 9 Reste unsubstituiert oder substituiert ist, vorzugsweise unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Cyano, Thiocyanato, (Cι-C4)Alkyl, (d-C4)Haloalkyl, (C1-C4)Alkoxy, (Cι-C4)Haloalkoxy, (C1-C4)- Alkylthio, (CrC )Haloalkylthio, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (C3-C6)Cycloalkyl, [(C1-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C )- alkylamino-carbonyl und Di(d-C )alkylamino-carbonyl substituiert ist, bedeuten, oder zwei benachbarte Reste X bedeuten gemeinsam einen ankondensierten Cyclus mit 4 bis 6 Ringatomen, der carbocyclisch ist oder Heteroringatome aus der Gruppe O, S und N enthält und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Cι-C4)Alkyl und Oxo substituiert ist.(X) n denotes n substituents X, the radicals X preferably each independently of the other halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, aminocarbonyl or (C 1 -C 4 ) alkyl, (CrC 4 ) alkoxy, (C 1 C -C 4 ) alkylthio, mono (dC 4 ) alkylamino, di (CC 4 ) alkylamino, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, [(dC 4 ) alkyl] carbonyl, [(dC 4 ) alkoxy] carbonyl, mono (-C-C 4 ) alkylamino-carbonyl, di (dC 4 ) alkylamino-carbonyl, N- (CrC 6 ) alkanoyl-amino or N- (Cι-C 4 ) alkanoyl-N- (Cι -C 4 ) alkyl-amino, where each of the latter 13 radicals is unsubstituted or substituted, preferably unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (-C-C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (CC 4 ) alkylthio, mono (dC 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkylamino, [(dC 4 ) alkyl] carbonyl, [(-C-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino-carbonyl, di (dC 4 ) alkylamino-carbonyl , Phenyl, phenoxy, phenylthio, phenylcarbonyi, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyciylamino, wherein each of the last 8 radicals is unsubstituted or one or more substituents from the group halogen, nitro, cyano, (dC 4 ) alkyl, (dC 4 ) alkoxy, (dC 4 ) alkylthio, (dC 4 ) haloalkyl, (Cι-C ) Haloalkoxy, formyl, (-C-C) alkyl-carbonyl and (Cι-C) alkoxy-carbonyl, is substituted, or (C 3 -Cg) cycloalkyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio or Heterocyciylamino, where each of the latter 9 radicals is unsubstituted or substituted, preferably unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, (C 1 -C 4 ) alkyl, (dC 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (CrC) haloalkylthio, mono (Cι-C 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 3 -C 6 ) cycloalkyl, [(C 1 -C 4 ) alkyl] carbonyl, [(Cι-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C) - alkylamino-carbonyl and di (dC) alkylamino carb onyl is substituted, or two adjacent radicals X together represent a fused-on cycle with 4 to 6 ring atoms, which is carbocyclic or contains hetero ring atoms from the group O, S and N and which is unsubstituted or by one or more radicals from the group halogen, (-C-C 4 ) alkyl and oxo is substituted.
n ist dabei vorzugsweise 0, 1 , 2 oder 3, insbesondere 0, 1 oder 2.n is preferably 0, 1, 2 or 3, in particular 0, 1 or 2.
(X)n bedeutet weiter bevorzugt n Substituenten X, wobei die Reste X jeweils unabhängig voneinander Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Cyano, Thiocyanato, (Cι-C4)Alkyl, Cyano-(CrC )alkyl, (Cι-C )Alkoxy, (Cι-C4)Alkylamino, Di-[(d-C )alkyl]-amino, Halo-(Cι-C4)alkyl, Hydroxy- (C1-C4)alkyl) (C1-C4)Alkoxy-(C1-C4)alkyl, Halo(d-C4)alkoxy-(C C4)alkyl, (Cι-C4)Alkylthio, Halo-(d-C4)alkylthio, (C2-C6)Alkenyl, Halo-(C2-C6)Alkenyl, (C2-C6)Alkinyl, Halo-(C2-C6)alkinyl, (Cι-C4)Alkylamino-(d-C4)alkyl, Di-[(C1-C4)alkyl]-amino-(C1-C4)alkyl, (C3-C6)Cycloalkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkyl, Heterocyclyl-(C1-C )alkyl mit 3 bis 9 Ringgliedern, wobei die cyclischen Gruppen in den letztgenannten 3 Resten unsubstituiert oder durch einen oder mehrere Reste, vorzugsweise bis zu drei Reste, aus der Gruppe (d-C4)Alkyl, Halogen und Cyano substituiert sind, oder Phenyl, Phenoxy, Phenylcarbonyl, Phenylcarbonyl-(CrC4)alkyl, (Cι-C )Alkoxy-carbonyl-(d-C4)alkyl, (C1-C4)Alkylamino-carbonyl-(d-C4)alkyl, (Cι-C )Alkyl-carbonyl, (Cι-C4)Alkoxy-carbonyl, Aminocarbonyl, (d-C )Alkylamino-carbonyl, Phenoxy-(C C )alkyl, Phenyl-(Cι-C )aIkyl, Heterocyclyl, Heterocyciylamino, Heterocyclyloxy, Heterocyclylthio oder einen der letztgenannten 16 Reste, der im acyclischen Teil oder, vorzugsweise, im cyclischen Teil durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Cyano, (C1-C4)Alkyl, (Cι-C4)Alkoxy, (d-C4)Alkylthio, (d-C4)Haloalkyl, (CrC )Haloalkoxy, Formyl, (d-C4)Alkyl-carbonyl, (CrC4)Alkoxy-carbonyl, (Cι-C )Alkoxy, substituiert ist, wobei Heterocyclyl in den Resten jeweils 3 bis 9 Ringatome und 1 bis 3 Heteroringatome aus der Gruppe N, O und S enthält, bedeuten, oder zwei benachbarte Reste X bedeuten gemeinsam einen ankondensierten Cyclus mit 4 bis 6 Ringatomen, der carbocyclisch ist oder Heteroringatome aus der Gruppe O, S und N enthält und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Cι-C )Alkyl und Oxo substituiert ist.(X) n further preferably denotes n substituents X, the radicals X each independently of one another halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, (C 1 -C 4 ) alkyl, cyano- (CrC) alkyl, ( -C-C) alkoxy, (-C-C 4 ) alkylamino, di - [(dC) alkyl] -amino, halo (Cι-C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl ) (C 1 - C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo (dC 4 ) alkoxy- (CC 4 ) alkyl, (Cι-C 4 ) alkylthio, halo- (dC 4 ) alkylthio, (C 2 -C 6 ) Alkenyl, halo (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, halo- (C 2 -C 6 ) alkynyl, (Cι-C 4 ) alkylamino- (dC 4 ) alkyl, Di - [(C 1 -C 4 ) alkyl] amino- (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkyl , Heterocyclyl- (C 1 -C) alkyl with 3 to 9 ring members, the cyclic groups in the latter 3 residues unsubstituted or by one or more residues, preferably up to three residues, from the group (dC 4 ) alkyl, halogen and Cyano are substituted, or phenyl, phenoxy, phenylcarbonyl, phenylcarbonyl- (CrC 4 ) alkyl, (-C-C) alkoxy-carbonyl- (dC 4 ) alkyl, (C 1 -C 4 ) alkylamino-carbonyl- (dC 4 ) alkyl , (-C-C) alkyl-carbonyl, (-C-C 4 ) alkoxy-carbonyl, aminocarbonyl, (dC) alkylamino-carbonyl, phenoxy- (CC) alkyl, phenyl- (Cι-C) aIkyl, heterocyclyl, heterocyciylamino, heterocyclyloxy , Heterocyclylthio or one of the latter 16 radicals, in the acyclic part or, preferably, in the cyclic part by one or more radicals from the group halogen, nitro, cyano, (C 1 -C 4 ) alkyl, (-C-C 4 ) alkoxy , (dC 4 ) alkylthio, (dC 4 ) haloalkyl, (CrC) haloalkoxy, formyl, (dC 4 ) alkyl-carbonyl, (CrC 4 ) alkoxy-carbonyl, (-C-C) alkoxy, is substituted, heterocyclyl in the radicals each containing 3 to 9 ring atoms and 1 to 3 hetero ring atoms from the group N, O and S. , mean, or two adjacent radicals X together represent a fused-on cycle with 4 to 6 ring atoms, which is carbocyclic or contains hetero ring atoms from the group O, S and N and which is unsubstituted or by one or more radicals from the group halogen, (Cι- C) alkyl and oxo is substituted.
(X)n bedeutet besonders bevorzugt n Substituenten X, wobei die Reste X jeweils unabhängig voneinander Halogen, OH, N02, CN, SCN, (Cι-C6)Alkyl, (Cι-C6)Alkoxy, (d-C4)Alkylcarbonyl oder (Cι-C4)Alkyloxycarbonyl, wobei die letztgenannten vier Reste unsubstituiert oder durch Halogen oder (Cι-C )Alkoxy substituiert sind, bedeuten, und bedeutet ganz besonders bevorzugt n Substituenten X, wobei die Reste X jeweils unabhängig voneinander Halogen, Hydroxy, (d-C4)Alkyl oder (Cι-C4)Alkoxy bedeuten. Heterocyclyl bedeutet in den vorstehend oder weiter unten genannten Resten unabhängig voneinander vorzugsweise einen heterocyclischen Rest mit 3 bis 7 Ringatomen und 1 bis 3 Heteroatomen aus der Gruppe N, O und S, vorzugsweise ein heteroaromatischer Rest aus der Gruppe Pyridyl, Pyrimidinyl, Pyridazinyl, Pyrazinyi, Triazinyl, Thienyl, Thiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Furyl, Pyrrolyl, Pyrazolyl, Imidazolyl und Triazolyl oder ein partiell oder vollständig hydrierter heterocylischer Rest aus der Gruppe Oxiranyl, Oxetanyl, Oxolanyl (= Tetrahydrofuryl), Oxanyl, Pyrrolidyl, Piperidyl, Piperazinyl, Dioxolanyl, Oxazolinyl, Isoxazolinyl, Oxazolidinyl, Isoxazolidinyl und Morpholinyl.(X) n particularly preferably denotes n substituents X, where the radicals X are each, independently of one another, halogen, OH, N0 2 , CN, SCN, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy, (dC 4 ) alkylcarbonyl or (-CC 4 ) alkyloxycarbonyl, the latter four radicals being unsubstituted or substituted by halogen or (-C-C) alkoxy, and very particularly preferably denotes n substituents X, where the radicals X are each independently halogen, hydroxy, (dC 4 ) alkyl or (-C-C 4 ) alkoxy mean. Heterocyclyl in the radicals mentioned above or further below, independently of one another, preferably denotes a heterocyclic radical having 3 to 7 ring atoms and 1 to 3 heteroatoms from the group N, O and S, preferably a heteroaromatic radical from the group pyridyl, pyrimidinyl, pyridazinyl, pyrazinyi, Triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl, imidazolyl and triazolyl or a partially or completely hydrogenated heterocyl radical from the group oxiranyl, oxetanyl, oxolanyl (= tetrahydrofuryl, piperyl, piperyl, piperyl, piperyl Dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl.
Besonders bevorzugt bedeutet Heterocyclyl einen heterocyclischen Rest mit 3 bis 6 Ringatomen und einem (1) Heteroatom aus der Gruppe N, O und S, insbesondere einen heteroaromatischen Rest mit 5 oder 6 Ringatomen oder einer gesättigten oder teilweise ungesättigten heterocyclischen (nicht heteroaromatischen) Rest mit 3 bis 6 Ringatomen.Heterocyclyl particularly preferably denotes a heterocyclic radical with 3 to 6 ring atoms and one (1) heteroatom from the group N, O and S, in particular a heteroaromatic radical with 5 or 6 ring atoms or a saturated or partially unsaturated heterocyclic (non-heteroaromatic) radical with 3 up to 6 ring atoms.
Außerdem bedeutet Heterocyclyl bevorzugt einen heterocyclischen Rest mit 5 oder 6In addition, heterocyclyl preferably denotes a heterocyclic radical with 5 or 6
Ringatomen und mit 2 oder 3 Heteroatomen aus der Gruppe N, O und S, insbesondere Pyrimidinyl, Pyridazinyl, Pyrazinyi, Triazinyl, Thiazolyl, Thiadiazolyl,Ring atoms and with 2 or 3 heteroatoms from the group N, O and S, in particular pyrimidinyl, pyridazinyl, pyrazinyi, triazinyl, thiazolyl, thiadiazolyl,
Oxazolyl, Isoxazolyl, Pyrazolyl, Imidazolyl, Triazolyl oderOxazolyl, isoxazolyl, pyrazolyl, imidazolyl, triazolyl or
Piperazinyl, Dioxolanyl, Oxazolinyl, Isoxazolinyl, Oxazolidinyl, Isoxazolidinyl oderPiperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl or
Morpholinyl.Morpholinyl.
Die zusammengesetzte Gruppe -A2-R2 ist vorzugsweise Cyclopropyl (hiernach auch „c-Pr"), CH2-c-Pr, -(CH2)2-c-Pr, Cyclobutyl (hiernach auch „c-Bu"), CH2-c-Bu; (CH2)2- c-Bu, Oxiranyl, Oxiranyl-methyl oder 2-(Oxiranyl)-eth-1-yl.The composite group -A 2 -R 2 is preferably cyclopropyl (hereinafter also “c-Pr”), CH 2 -c-Pr, - (CH 2 ) 2 -c-Pr, cyclobutyl (hereinafter also “c-Bu”) , CH 2 -c-Bu; (CH 2 ) 2 - c-Bu, oxiranyl, oxiranyl-methyl or 2- (oxiranyl) -eth-1-yl.
Gegenstand der vorliegenden Erfindung sind auch Verfahren zur Herstellung von Verbindungen der Formel (I) und deren Salze,The present invention also relates to processes for the preparation of compounds of the formula (I) and their salts,
worin A1, A2, L°, R1, R2, R3, R4, X und n wie oben definiert sind, dadurch gekennzeichnet, daß man wherein A 1 , A 2 , L °, R 1 , R 2 , R 3 , R 4 , X and n are as defined above, characterized in that
a) im Falle, dass R3 in Formel (I) eine Gruppe der Formel -L1-N=C(U1)(U3) ist, wobei L1, U1 und U3 wie weiter oben unter R3 definiert sind, eine Verbindung der Formel (II),a) in the case where R 3 in formula (I) is a group of the formula -L 1 -N = C (U 1 ) (U 3 ), where L 1 , U 1 and U 3 are as defined above under R 3 are a compound of formula (II),
worin A1, A2, L°, L1, R1, R2, R4, X und n wie in Formel (I) definiert sind, mit einer Verbindung der Formel (III),wherein A 1 , A 2 , L °, L 1 , R 1 , R 2 , R 4 , X and n are as defined in formula (I), with a compound of formula (III),
worin U1 und U3 wie in Formel (I) definiert sind und R18 und R19 unabhängig voneinander jeweils für gegebenenfalls substituiertes Alkyl mit bis zu 12 C-Atomen, vorzugsweise für (Cι-C4)Alkyl stehen oder gemeinsam verbunden eine Alkylengruppe mit 2 bis 4 C-Atomen bedeuten, umsetzt oderwherein U 1 and U 3 are as defined in formula (I) and R 18 and R 19 independently of one another each represent optionally substituted alkyl having up to 12 carbon atoms, preferably (C 1 -C 4 ) alkyl or are joined together to form an alkylene group with 2 to 4 carbon atoms mean, or
b) im Falle, dass R3 in Formel (I) eine Gruppe der Formel -L1-NG1-C(U2)=N-U4 ist, wobei L1, G1, U2 und U4 wie weiter oben für R3 definiert sind, eine Verbindung der Formel (IV), b) in the case where R 3 in formula (I) is a group of the formula -L 1 -NG 1 -C (U 2 ) = NU 4 , where L 1 , G 1 , U 2 and U 4 are as above for R 3 are defined, a compound of the formula (IV),
worin A1, A2, L°, L1, R1, R2, R4, G1, X und n wie in Formel (I) definiert sind, mit einer Verbindung derwherein A 1 , A 2 , L °, L 1 , R 1 , R 2 , R 4 , G 1 , X and n are as defined in formula (I), with a compound of
worin U und U wie in Formel (I) und R »18 wie in Formel (III) definiert sind, umsetzt oderwherein U and U are as defined in formula (I) and R 18 as defined in formula (III), or
c) im Falle, dass R3 in Formel (I) eine Gruppe der Formel -L1-N=C(U1)(U3) ist, wobei U3 = NG18NG19G20, NG21OG22 oder NG23SG24 bedeutet und L1, U1, G18,c) in the case where R 3 in formula (I) is a group of the formula -L 1 -N = C (U 1 ) (U 3 ), where U 3 = NG 18 NG 19 G 20 , NG 21 OG 22 or NG 23 SG 24 means and L 1 , U 1 , G 18 ,
Q19 G20j 2^ G22ι G23j G24 wje wejter Qben ^ R3 defjnjert sjnd ejne Q 19 G 2 0j 2 ^ G 2 2ι G 2 3j G 24 wje wejter Qben ^ R 3 def j n j ert sjnd ejne
Verbindung der Formel (VI),Compound of formula (VI),
worin A1, A2, L°, L1, R1, R2, R4, U1, X und n wie in Formel (I) definiert sind und R6 und R7 wie weiter oben definiert sind, mit einer Verbindung der Formel (VII) bzw. deren Säureaddukten,wherein A 1 , A 2 , L °, L 1 , R 1 , R 2 , R 4 , U 1 , X and n are as defined in formula (I) and R 6 and R 7 are as defined above, with one Compound of formula (VII) or their acid adducts,
H-U3 (VII) worin U3 wie in Formel (I) definiert ist, umsetzt oder d) im Falle, dass R3 in Formel (I) eine Gruppe der Formel -L1-N=C(U1)(U3) ist, wobei U1 = R14 und U3 = R15 bedeuten und l_\ R14 und R15 wie weiter oben definiert sind, eine Verbindung der Formel (II) gemäß Variante a) mit einem Aldehyd bzw. Keton der Formel (VIII),HU 3 (VII) wherein U 3 is as defined in formula (I), or d) in the case where R 3 in formula (I) is a group of the formula -L 1 -N = C (U 1 ) (U 3 ), where U 1 = R 14 and U 3 = R 15 and l_ \ R 14 and R 15 as defined above, a compound of the formula (II) according to variant a) with an aldehyde or ketone of the formula (VIII),
U1-CO-U3 (VIII)U 1 -CO-U 3 (VIII)
worin U1 und U3 wie in Formel (I) definiert sind, umsetzt.wherein U 1 and U 3 are as defined in formula (I).
Die beim erfindungsgemäßen Verfahren, Variante a) zur Herstellung von Verbindungen der Formel (I) verwendeten substituierten Aminotriazine der Formel (II) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl. WO-A-9965882).The substituted aminotriazines of the formula (II) used in the process according to the invention, variant a) for the preparation of compounds of the formula (I) are known and / or can be prepared by processes known per se (cf. WO-A-9965882).
Die Ausgangsstoffe der allgemeinen Formel (III) sind bekannt (vgl. Chem. Ber. 89, 2060 (1956), Liebigs Anm. Chem. 641 , 1 (1961), Chem. Ber. 96, 1350 (1963)) oder können analog den bekannten Verfahren hergestellt werden.The starting materials of the general formula (III) are known (cf. Chem. Ber. 89, 2060 (1956), Liebigs Anm. Chem. 641, 1 (1961), Chem. Ber. 96, 1350 (1963)) or can be analog the known methods are produced.
Das erfindungsgemäße Verfahren zur Herstellung von Verbindungen der allgemeinen Formel (I) wird in der Variante a) gegebenenfalls unter Verwendung eines Verdünnungsmittels durchgeführt. Als Verdünnungsmittel kommen hierbei vor allem inerte organische Lösungsmittel in Betracht. Hierzu gehören insbesondere aliphatische, alicyclische oder aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe, wie beispielsweise Benzin, Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzol, Petrolether, Hexan, Cyclohexan, Dichlormethan, Chloroform, Tetrachlorkohlenstoff; Ether, wie Diethylether, Diisopropylether, Dioxan, Tetrahydrofuran oder Ethylenglykoldimethyl- oder -diethylether; Ketone, wie Aceton, Butanon oder Methyl-isobutylketon; Nitrile, wie Acetonitril, Propionitril oder Butyronitril; Amide, wie N,N-Di-methylformamid, N,N-Dimethylacetamid, N-Methyl- formanilid, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid; Ester wie Essigsäuremethylester oder Essigsäureethylester; Sulfoxide, wie Dimethylsulfoxid, Alkohole, wie Methanol, Ethanol, n- oder i-Propanol, Ethylenglykolmonomethylether, Ethylenglykolmonoethylether, Diethylenglykolmonomethylether oder Diethylenglykolmonoethylether.Variant a) of the process according to the invention for the preparation of compounds of the general formula (I) is carried out, if appropriate, using a diluent. Inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides, such as dimethyl sulfoxide, Alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens in einem größeren Bereich variiert werden. Im Allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 150°C, vorzugsweise zwischen 10°C und 120°C.The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
Das erfindungsgemäße Verfahren wird in der Regel unter Normaldruck durchgeführt. Es ist jedoch auch möglich, das erfindungsgemäße Verfahren unter erhöhtem oder vermindertem Druck - im allgemeinen zwischen 0,1 bar und 10 bar - durchzuführen.The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
Zur Durchführung des erfindungsgemäßen Verfahrens werden die Ausgangsstoffe beispielsweise in äquimolaren Mengen eingesetzt. Es ist jedoch auch möglich, eine der Komponenten in einem mehr oder weniger großen Überschuß zu verwenden, z. B. wenn die im Unterschuss eingesetzte Komponente schnell abreagieren soll, um Nebenreaktionen zu vermindern. Die Umsetzung wird beispielsweise in einem geeigneten Verdünnungsmittel in Gegenwart eines Reaktionshilfsmittels durchgeführt, wobei das Reaktionsgemisch in der Regel mehrere Stunden bei der erforderlichen Temperatur durchmischt, beispielsweise gerührt wird. Die Aufarbeitung kann nach üblichen Methoden durchgeführt werden (vgl. auch die Herstellungsbeispiele).To carry out the process according to the invention, the starting materials are used, for example, in equimolar amounts. However, it is also possible to use one of the components in a more or less large excess, e.g. B. if the component used in the deficit should react quickly to reduce side reactions. The reaction is carried out, for example, in a suitable diluent in the presence of a reaction auxiliary, the reaction mixture generally being mixed, for example stirred, at the required temperature for several hours. The work-up can be carried out using customary methods (cf. also the preparation examples).
Die beim erfindungsgemäßen Verfahren, Variante b) zur Herstellung von Verbindungen der Formel (I) verwendeten substituierten Aminotriazine der Formel (IV) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl. WO-A-9965882).The substituted aminotriazines of the formula (IV) used in the process according to the invention, variant b) for the preparation of compounds of the formula (I) are known and / or can be prepared by processes known per se (cf. WO-A-9965882).
Die Verbindungen der Formel (V) sind z.B. bekannt aus J. Org. Chem. 30, S. 2531- 2533 (1965). Das erfindungsgemäße Verfahren zur Herstellung von Verbindungen der allgemeinen Formel (I) nach Variante b) wird gegebenenfalls unter Verwendung eines Verdünnungsmittels durchgeführt. Als Verdünnungsmittel kommen hierbei vor allem inerte organische Lösungsmittel in Betracht. Hierzu gehören insbesondere aliphatische, alicyclische oder aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe, wie beispielsweise Benzin, Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzol, Petrolether, Hexan, Cyclohexan, Dichlormethan, Chloroform, Tetrachlorkohlenstoff; Ether, wie Diethylether, Diisopropylether, Dioxan, Tetrahydrofuran oder Ethylenglykoldimethyl- oder -diethylether; Ketone, wie Aceton, Butanon oder Methyl-isobutylketon; Nitrile, wie Acetonitril, Propionitril oder Butyronitril; Amide, wie N.N-Di-methyiformamid, N,N-Dimethylacetamid, N-Methyl- formanilid, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid; Ester wie Essigsäuremethylester oder Essigsäureethylester; Sulfoxide, wie Dimethylsulfoxid, Alkohole, wie Methanol, Ethanol, n- oder i-Propanol, Ethylenglykolmonomethylether, Ethylenglykolmonoethylether, Diethylenglykolmonomethylether oder Diethylenglykolmonoethylether.The compounds of formula (V) are known, for example, from J. Org. Chem. 30, pp. 2531-2533 (1965). The process according to the invention for the preparation of compounds of the general formula (I) according to variant b) is optionally carried out using a diluent. Inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as NN-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 150°C, vorzugsweise zwischen 10°C und 120°C.The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
Das erfindungsgemäße Verfahren nach Variante b) wird in einfacher Weise beispielsweise unter Normaldruck durchgeführt. Es ist jedoch auch möglich, das erfindungsgemäße Verfahren unter erhöhtem oder vermindertem Druck - vorzugsweise zwischen 0,1 bar und 10 bar- durchzuführen.The inventive method according to variant b) is carried out in a simple manner, for example under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - preferably between 0.1 bar and 10 bar.
Zur Durchführung des Verfahrens nach Variante b) können die Ausgangsstoffe in äquimolaren Mengen eingesetzt werden. Es ist jedoch auch möglich, eine der Komponenten in einem mehr oder weniger großen Überschuß zu verwenden. Die Umsetzung wird vorzugsweise in einem geeigneten Verdünnungsmittel in Gegenwart eines Reaktionshilfsmittels durchgeführt. Die Reaktion läuft in der Regel innerhalb mehrerer Stunden unter Rühren bei der erforderlichen Temperatur vollständig ab. Die Aufarbeitung kann nach üblichen Methoden durchgeführt werden (vgl. die Herstellungsbeispiele).To carry out the process according to variant b), the starting materials can be used in equimolar amounts. However, it is also possible to use one of the components in a more or less large excess. The reaction is preferably carried out in a suitable diluent in the presence of a reaction auxiliary. The reaction usually runs completely within several hours with stirring at the required temperature. The work-up can be carried out by customary methods (cf. the production examples).
Zur Herstellung der Verbindungen (I) nach Variante c) werden Verbindungen der Formel (VI) eingesetzt. Verbindungen der Formel (VI) können nach Variante a) aus Aminoverbindungen der Formel (II) hergestellt werden, z.B. durch Umsetzung mit Verbindungen der Formel (III), worin U1, R18, R19 wie Formel (III) definiert sind und U3 = NR6R7 ist, worin R6 und R7 wie in Formel (I) definiert sind (= Verbindungen (lila)). Die Verbindungen der Formel (VII) sind bekannt oder können nach bekannten Methoden hergestellt werden.Compounds of the formula (VI) are used to prepare the compounds (I) according to variant c). Compounds of the formula (VI) can be prepared according to variant a) from amino compounds of the formula (II), for example by reaction with compounds of the formula (III) in which U 1 , R 18 , R 19 are defined as formula (III) and U 3 = NR 6 R 7 , where R 6 and R 7 are as defined in formula (I) (= compounds (purple)). The compounds of formula (VII) are known or can be prepared by known methods.
Das erfindungsgemäße Verfahren nach Variante c) wird gegebenenfalls unter Verwendung eines Verdünnungsmittels durchgeführt. Als Verdünnungsmittel kommen hierbei vor allem inerte organische Lösungsmittel in Betracht. Hierzu gehören insbesondere aliphatische, alicyclische oder aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe, wie beispielsweise Benzin, Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzol, Petrolether, Hexan, Cyclohexan, Dichlormethan, Chloroform, Tetrachlorkohlenstoff; Ether, wie Diethylether, Diisopropylether, Dioxan, Tetrahydrofuran oder Ethylenglykoldimethyl- oder -diethylether; Ketone, wie Aceton, Butanon oder Methyl-isobutylketon; Nitrile, wie Acetonitril, Propionitril oder Butyronitrii; Amide, wie N,N-Di-methylformamid, N,N-Dimethylacetamid, N-Methyl- formanilid, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid; Ester wie Essigsäuremethylester oder Essigsäureethylester; Sulfoxide, wie Dimethylsulfoxid, Alkohole, wie Methanol, Ethanol, n- oder i-Propanol, Ethylenglykolmonomethylether, Ethylenglykolmonoethylether, Diethylenglykolmonomethylether oder Diethylenglykolmonoethylether.The method according to variant c) according to the invention is optionally carried out using a diluent. Inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrii; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether.
Die anderen Reaktionsbedingungen wie Bereiche für Reaktionstemperaturen, Druckbedingungen, Mengenverhältnisse etc. sind denen in den Varianten a) und b) vergleichbar. Das erfindungsgemäße Verfahren nach Variante d) wird gegebenenfalls unter Verwendung eines Verdünnungsmittels durchgeführt. Als Verdünnungsmittel kommen hierbei vor allem inerte organische Lösungsmittel in Betracht. Hierzu gehören insbesondere aliphatische, alicyclische oder aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe, wie beispielsweise Benzin, Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzol, Petrolether, Hexan, Cyclohexan, Dichlormethan, Chloroform, Tetrachlorkohlenstoff; Ether, wie Diethylether, Diisopropylether, Dioxan, Tetrahydrofuran oder Ethylenglykoldimethyl- oder -diethylether; Ketone, wie Aceton, Butanon oder Methyl-isobutylketon; Nitrile, wie Acetonitril, Propionitril oder Butyronitril; Amide, wie N,N-Di-methylformamid, N,N-Dimethylacetamid, N-Methyl- formanilid, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid; Ester wie Essigsäuremethylester oder Essigsäureethylester; Sulfoxide, wie Dimethylsulfoxid, Alkohole, wie Methanol, Ethanol, n- oder i-Propanol, Ethylenglykolmonomethylether, Ethylenglykolmonoethylether, Diethylenglykolmonomethylether oder Diethylenglykolmonoethylether.The other reaction conditions such as ranges for reaction temperatures, pressure conditions, quantitative ratios etc. are comparable to those in variants a) and b). The method according to variant d) according to the invention is optionally carried out using a diluent. Inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether.
Die in dem Verfahren nach Variante d) eingesetzten Verbindungen der Formel (VIII) sind bekannt oder können nach bekannten Verfahren hergestellt werden.The compounds of formula (VIII) used in the process according to variant d) are known or can be prepared by known processes.
Die anderen Reaktionsbedingungen wie Bereiche für Reaktionstemperaturen, Druckbedingungen, Mengenverhältnisse etc. sind denen in den Varianten a) und b) und c) vergleichbar.The other reaction conditions such as ranges for reaction temperatures, pressure conditions, quantitative ratios etc. are comparable to those in variants a) and b) and c).
Das bei der Reaktion frei werdende Wasser (Reaktionswasser) kann z. B. durch azetrope Destillation, wasserbindende Salze oder Molekularsiebe entfernt werden.The water released during the reaction (water of reaction) can be e.g. B. by acetrope distillation, water-binding salts or molecular sieves.
Die jeweiligen Ausgangsverbindungen der Formeln (II) bis (VIII) sind bekannt oder können nach den oben angegebenen Methoden oder analog bekannten Verfahren hergestellt werden. Zur Herstellung der Säureadditionssalze der Verbindungen der Formel (I) kommen folgende Säuren in Frage: Halogenwasserstoffsäuren wie Chlorwasserstoffsäure oder Bromwasserstoffsäure, weiterhin Phosphorsäure, Salpetersäure, Schwefelsäure, mono- oder bifunktionelle Carbonsäuren und Hydroxycarbonsäuren wie Essigsäure, Maleinsäure, Bernsteinsäure, Fumarsäure, Weinsäure, Citronensäure, Salicylsäure, Sorbinsäure oder Milchsäure, sowie Sulfonsäuren wie p-Toluolsulfonsäure oder 1 ,5-Naphthalindisulfonsäure. Die Säureadditionsverbindungen der Formel (I) können in einfacher Weise nach den üblichen Salzbildungsmethoden, z.B. durch Lösen einer Verbindung der Formel (I) in einem geeigneten organischen Lösungsmittel wie z.B. Methanol, Aceton, Methylenchlorid oder Benzin und Hinzufügen der Säure bei Temperaturen von 0 bis 100°C erhalten werden und in bekannter Weise, z.B. durch Abfiltrieren, isoliert und gegebenfalls durch Waschen mit einem inerten organischen Lösemittel gereinigt werden.The respective starting compounds of the formulas (II) to (VIII) are known or can be prepared by the methods indicated above or by methods known analogously. The following acids are suitable for the preparation of the acid addition salts of the compounds of the formula (I): hydrohalic acids such as hydrochloric acid or hydrobromic acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- or bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid Salicylic acid, sorbic acid or lactic acid, and sulfonic acids such as p-toluenesulfonic acid or 1, 5-naphthalenedisulfonic acid. The acid addition compounds of the formula (I) can be prepared in a simple manner by the customary salt formation methods, for example by dissolving a compound of the formula (I) in a suitable organic solvent such as methanol, acetone, methylene chloride or gasoline and adding the acid at temperatures from 0 to 100 ° C are obtained and isolated in a known manner, for example by filtering, and optionally cleaned by washing with an inert organic solvent.
Die Basenadditionssalze der Verbindungen der Formel (I) werden vorzugsweise in inerten polaren Lösungsmitteln wie z.B. Wasser, Methanol oder Aceton bei Temperaturen von 0 bis 100 C hergestellt. Geeignete Basen zur Herstellung der erfindungsgemäßen Salze sind beispielsweise Alkalicarbonate, wie Kaliumcarbonat, Alkali- und Erdalkalihydroxide, z.B. NaOH oder KOH, Alkali- und Erdalkalihydride, z.B. NaH, Alkali- und Erdalalkoholate, z.B. Natriummethanolat, Kalium-tert.Butylat, oder Ammoniak oder Ethanolamin. Quartäre Ammoniumsalze können z.B. durch Umsalzung oder Kondensation mit quartären Ammoniumsalzen der FormelThe base addition salts of the compounds of formula (I) are preferably in inert polar solvents such as e.g. Water, methanol or acetone at temperatures from 0 to 100 C. Suitable bases for the preparation of the salts according to the invention are, for example, alkali carbonates, such as potassium carbonate, alkali and alkaline earth metal hydroxides, e.g. NaOH or KOH, alkali and alkaline earth hydrides, e.g. NaH, alkali and alkaline alcoholates, e.g. Sodium methoxide, potassium tert-butoxide, or ammonia or ethanolamine. Quaternary ammonium salts can e.g. by salting or condensation with quaternary ammonium salts of the formula
[NRR'R"R"']+X-, worin R, [NRR'R "R"'] + X-, where R,
Phenyl oder Benzyl bedeuten und X" ein Anion, z.B. CI" bzw. OH" ist.Phenyl or benzyl and X "is an anion, for example CI " or OH " .
Mit den in den vorstehenden Verfahrensvarianten bezeichneten "inerten Lösungsmitteln" sind jeweils Lösungsmittel gemeint, die unter den jeweiligen Reaktionsbedingungen inert sind, jedoch nicht unter beliebigen Reaktionsbedingungen inert sein müssen. Eine Kollektion aus Verbindungen (I), die nach den obengenannten Verfahren synthetisiert werden können, können zusätzlich in parallelisierter Weise hergestellt werden , wobei dies in manueller, teilweise automatisierter oder vollständig automatisierter Weise geschehen kann. Dabei ist es möglich, sowohl die Reaktionsdurchführung, die Aufarbeitung oder die Reinigung der Produkte bzw. Zwischenstufen zu automatisieren. Insgesamt wird hierunter eine Vorgehensweise verstanden, wie sie beispielsweise durch S. H. DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis", Band 1 , Verlag Escom, 1997, Seite 69 bis 77 beschrieben wird.The “inert solvents” referred to in the above process variants mean in each case solvents which are inert under the respective reaction conditions but do not have to be inert under any reaction conditions. A collection of compounds (I) which can be synthesized according to the above-mentioned methods can additionally be produced in a parallelized manner, which can be done in a manual, partially automated or fully automated manner. It is possible to automate the implementation of the reaction, the processing or the cleaning of the products or intermediate stages. Overall, this is understood to mean a procedure as described, for example, by SH DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis", Volume 1, Escom Verlag, 1997, pages 69 to 77.
Zur parallelisierten Reaktionsdurchführung und Aufarbeitung können eine Reihe von im Handel erhältlichen Geräten verwendet werden wie sie beispielsweise von den Firmen Stern Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England oder H + P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleißheim, Deutschland angeboten werden. Für die parallelisierte Aufreinigung von Verbindungen (I) oder von bei der Herstellung anfallenden Zwischenprodukten stehen unter anderem Chromatographieapparaturen zur Verfügung, beispielsweise der Firma ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. Die aufgeführten Apparaturen ermöglichen eine modulare Vorgehensweise, bei der die einzelnen Arbeitsschritte automatisiert sind, zwischen den Arbeitsschritten jedoch manuelle Operationen durchgeführt werden müssen. Dies kann durch den Einsatz von teilweise oder vollständig integrierten Automationssystemen umgangen werden, bei denen die jeweiligen Automationsmodule beispielsweise von Roboter bedient werden. Derartige Automationssysteme können zum Beispiel von der Firma Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA bezogen werden.A number of commercially available devices can be used for parallelized reaction execution and processing, for example those offered by Stern Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England or H + P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleissheim, Germany become. Chromatography apparatus, for example from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA, is available for the parallelized purification of compounds (I) or of intermediate products obtained during production. The equipment listed enables a modular procedure in which the individual work steps are automated, but manual operations must be carried out between the work steps. This can be avoided by using partially or fully integrated automation systems in which the respective automation modules are operated by robots, for example. Automation systems of this type can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA.
Neben den beschriebenen Methoden kann die Herstellung von Verbindungen (I) vollständig oder partiell durch Festphasen unterstützte Methoden erfolgen. Zu diesem Zweck werden einzelne Zwischenstufen oder alle Zwischenstufen der Synthese oder einer für die entsprechende Vorgehensweise angepaßten Synthese an ein Syntheseharz gebunden. Festphasen unterstützte Synthesemethoden sind in der Fachliteratur hinreichend beschrieben, z. B.: Barry A. Bunin in "The Combinatorial Index", Verlag Academic Press, 1998.In addition to the methods described, compounds (I) can be prepared completely or partially by methods supported by solid phases. For this purpose, individual intermediate stages or all intermediate stages of the synthesis or a synthesis adapted for the corresponding procedure are bound to a synthetic resin. Solid phase supported synthesis methods are in the specialist literature is adequately described, e.g. For example: Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998.
Die Verwendung von Festphasen unterstützten Synthesemethoden erlaubt eine Reihe von literaturbekannten Protokollen, die wiederum manuell oder automatisiert ausgeführt werden können. Zum Beispiel kann die "Teebeutelmethode" (Houghten, US 4,631 ,211 ; Houghten et al., Proc. Natl. Acad. Sei., 1985, 82, 5131 - 5135) mit Produkten der Firma IRORI, 11149 North Torrey Pines Road, La Jolla, CA 92037, USA teilweise automatisiert werden. Die Automatisierung von Festphasen unterstützter Parallelsynthese gelingt beispielsweise durch Apparaturen der Firmen Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA oder MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Deutschland.The use of synthesis methods supported by solid phases allows a number of protocols known from the literature, which in turn can be carried out manually or automatically. For example, the "teabag method" (Houghten, US 4,631,211; Houghten et al., Proc. Natl. Acad. Sei., 1985, 82, 5131-5135) can be used with products from IRORI, 11149 North Torrey Pines Road, La Jolla, CA 92037, USA can be partially automated. The automation of solid-phase-supported parallel synthesis is achieved, for example, by apparatus from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.
Die Herstellung gemäß der hier beschriebenen Verfahren liefert Verbindungen (I) in Form von Substanzkollektionen oder -bibliotheken. Gegenstand der vorliegenden Erfindung sind daher auch Bibliotheken der Verbindungen (I), die mindestens zwei Verbindungen (I) enthalten und deren Vorprodukten.The preparation according to the processes described here provides compounds (I) in the form of substance collections or libraries. The present invention therefore also relates to libraries of the compounds (I) which contain at least two compounds (I) and their precursors.
Die erfindungsgemäßen Verbindungen der Formel (I) und deren Salze, im Folgenden zusammen als (erfindungsgemäße) Verbindungen der Formel (I) bezeichnet, weisen eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler Schadpflanzen auf. Auch schwer bekämpfbare perennierende Unkräuter, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfaßt. Dabei ist es gleichgültig, ob die Substanzen im Vorsaat-, Vorauflauf- oder Nachauflaufverfahren ausgebracht werden.The compounds of the formula (I) according to the invention and their salts, hereinafter referred to collectively as (compounds) of the formula (I) according to the invention, have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants. Perennial weeds that are difficult to control and that sprout from rhizomes, rhizomes or other permanent organs are also well captured by the active ingredients. It does not matter whether the substances are applied by pre-sowing, pre-emergence or post-emergence.
Im Einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll.Some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned in detail, which can be controlled by the compounds according to the invention, without any intention that the name should limit them to certain species.
Auf der Seite der monokotylen Unkrautarten werden z.B. Agrostis, Alopecurus, Apera, Avena, Brachicaria, Bromus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Festuca, Fimbristylis, Ischaemum, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Sagittaria, Scirpus, Setaria, Sphenoclea, sowie Cyperusarten vorwiegend aus der annuellen Gruppe und auf Seiten der perennierenden Spezies Agropyron, Cynodon, Imperata sowie Sorghum und auch ausdauernde Cyperusarten gut erfaßt.On the side of the monocotyledon weed species, for example, Agrostis, Alopecurus, Apera, Avena, Brachicaria, Bromus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Festuca, Fimbristylis, Ischaemum, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Sagittaria, Scirpus, Setaria, Sphenoclea, as well as Cyperus species mainly from the annual group and on the part of the perennial species Agroponata, Cynodyron, Cyn as well as sorghum and perennial cyperus species.
Bei dikotylen Unkrautarten erstreckt sich das Wirkungsspektrum auf Arten wie z.B. Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon und Sida auf der annuellen Seite sowie Convolvulus, Cirsium, Rumex und Artemisia bei den perennierenden Unkräutern.With dicotyledon weed species, the spectrum of activity extends to species such as Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida on the annual side as well as Convolvulus, Cirsium, Rumex and Artemisia for the perennial weeds.
Außerdem wird herbizide Wirkung bei dikotylen Unkräutern wie Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rotala, Seneceio, Sesbania, Solanum, Sonchus, Taraxacum, Trifolium, Urtica und Xanthium erzielt.In addition, herbicidal activity in dicotyledon weeds such as Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rioaes, Sotala, Sotala, Sotala Solanum, Sonchus, Taraxacum, Trifolium, Urtica and Xanthium.
Unter den spezifischen Kulturbedingungen im Reis vorkommende Unkräuter wie z.B. Sagittaria, Alisma, Eleocharis, Scirpus und Cyperus werden von den erfindungsgemäßen Wirkstoffen ebenfalls hervorragend bekämpft.Weeds occurring in rice under the specific crop conditions, e.g. Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus are also superbly controlled by the active compounds according to the invention.
Werden die erfindungsgemäßen Verbindungen vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab.If the compounds according to the invention are applied to the surface of the earth before germination, either the weed seedlings emerge completely or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.
Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im Nachauflaufverfahren tritt ebenfalls sehr rasch nach der Behandlung ein drastischer Wachstumsstop ein und die Unkrautpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. Obgleich die erfindungsgemäßen Verbindungen eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen wie z.B. Weizen, Gerste, Roggen, Triticale, Reis, Mais, Zuckerrübe, Baumwolle und Soja nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Nutzpflanzungen inklusive Zierpflanzungen.When the active ingredients are applied to the green parts of the plants in the post-emergence process, there is also a drastic growth stop very quickly after the treatment and the weed plants remain in the growth stage at the time of application or die completely after a certain time, so that one for the crop plants harmful weed competition is eliminated very early and sustainably. Although the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops such as, for example, wheat, barley, rye, triticale, rice, corn, sugar beet, cotton and soybean are only insignificantly or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops, including ornamental crops.
Darüberhinaus weisen die erfindungsgemäßen Substanzen hervorragende wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativen Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da das Lagern hierdurch verringert oder völlig verhindert werden kann.In addition, the substances according to the invention have excellent growth-regulating properties in crop plants. They intervene in the plant's metabolism in a regulating manner and can thus be used to influence plant constituents in a targeted manner and to facilitate harvesting, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesired vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as this can reduce or completely prevent storage.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von bekannten oder noch zu entwickelnden gentechnisch veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregem von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z. B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt. Bevorzugt ist die Anwendung der erfindungsgemäßen Verbindungen der Formel (I) oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz-und Zierpflanzen, z. B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Vorzugsweise können die Verbindungen der Formel (I) als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind.Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of known or still to be developed genetically modified plants. The transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogen pathogens such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties concern e.g. B. the crop in terms of quantity, quality, storability, composition and special ingredients. Thus, transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known. Preference is given to using the compounds of the formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, for. B. of cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables. The compounds of the formula (I) can preferably be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made resistant to genetic engineering.
Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Verfahren erzeugt werden (siehe z. B. EP-A-0221044, EP-A- 0131624). Beschrieben wurden beispielsweise in mehreren Fällen gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/11376, WO 92/14827,Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants are, for example, classic breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be produced using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). In several cases, for example, genetic engineering changes in crop plants have been described in order to modify the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827,
WO 91/19806), transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom TypWO 91/19806), transgenic crop plants which are active against certain herbicides of the type
Glufosinate (vgl. z. B. EP-A-0242236, EP-A-242246) oder GlyphosateGlufosinate (see e.g. EP-A-0242236, EP-A-242246) or glyphosate
(WO 92/00377) oder der Sulfonylhamstoffe (EP-A-0257993, US-A-5013659) resistent sind, transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit(WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659) are resistant to transgenic crop plants, for example cotton, with the ability
Bacillus thuringiensis-Toxine (Bt-Toxine) zu produzieren, welche dieBacillus thuringiensis toxins (Bt toxins) which the
Pflanzen gegen bestimmte Schädlinge resistent machen (EP-A-0142924,Making plants resistant to certain pests (EP-A-0142924,
EP-A-0193259). transgene Kulturpflanzen mit modifizierter FettsäurezusammensetzungEP-A-0193259). transgenic crops with modified fatty acid composition
(WO 91/13972).(WO 91/13972).
Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind im Prinzip bekannt; siehe z.B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2. Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996 oder Christou, "Trends in Plant Science" 1 (1996) 423-431).In principle, numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known; see, e.g., Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene and Clones", VCH Weinheim 2nd edition 1996 or Christou, "Trends in Plant Science" 1 (1996) 423-431).
Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe der obengenannten Standardverfahren können z. B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA-Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden.For such genetic engineering manipulations, nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of the above standard procedures such. B. base exchanges, partial sequences removed or natural or synthetic sequences added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments.
Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines Cosuppressionseffektes oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet.The production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically cleaves transcripts of the gene product mentioned above.
Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA-Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA-Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind.For this purpose, DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z. B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 11 (1992), 3219- 3227; Wolter et al., Proc. Natl. Acad. Sei. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a particular compartment, z. B. the coding region can be linked to DNA sequences that localize in guarantee a certain compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1: 95-106 (1991).
Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen Pflanzenspezies handeln, d.h. sowohl monokotyle als auch dikotyle Pflanzen.The transgenic plant cells can be regenerated into whole plants using known techniques. The transgenic plants can in principle be plants of any plant species, i.e. both monocot and dicot plants.
So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen.Thus, transgenic plants are available which have changed properties due to overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.
Vorzugsweise können die erfindungsgemäßen Verbindungen (I) in transgenen Kulturen eingesetzt werden, welche gegen Herbizide aus der Gruppe der Sulfonylhamstoffe, Glufosinate-ammonium oder Glyphosate-isopropylammonium und analoge Wirkstoffe resistent sind.The compounds (I) according to the invention can preferably be used in transgenic crops which are resistant to herbicides from the group of the sulfonylureas, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active compounds.
Bei der Anwendung der erfindungsgemäßen Wirkstoffe in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen (I) als Herbizide zur Bekämpfung von Schadpflanzen in transgenen Kulturpflanzen.When the active compounds according to the invention are used in transgenic crops, in addition to the effects on harmful plants which can be observed in other crops, there are often effects which are specific to the application in the respective transgenic culture, for example a changed or specially expanded weed spectrum which can be controlled changed Application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing the growth and yield of the transgenic crop plants. The invention therefore also relates to the use of the compounds (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
Die erfindungsgemäße Verwendung zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen schließt auch den Fall ein, bei dem der Wirkstoff der Formel (I) oder dessen Salz erst nach der Ausbringung auf der Pflanze, in der Pflanze oder im Boden aus einer Vorläufersubstanz ("Prodrug") gebildet wird.The use according to the invention for controlling harmful plants or for regulating the growth of plants also includes the case in which the active compound of the formula (I) or its salt is obtained from a precursor substance only after application to the plant, in the plant or in the soil ("Prodrug ") is formed.
Die erfindungsgemäßen Verbindungen können in Form von Spritzpulvern, emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und pflanzenwachstumsregulierende Mittel, die Verbindungen der Formel (I) enthalten.The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations. The invention therefore also relates to herbicidal and plant growth-regulating compositions which comprise compounds of the formula (I).
Die Verbindungen der Formel (I) können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in-Wasser- und Wasserin-Öl-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Mikrokapseln und Wachse.The compounds of formula (I) can be formulated in different ways, depending on which biological and / or chemical-physical parameters are specified. Possible formulation options are, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), pickling agents, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and Adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Aufl. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London. Die notwendigen und verwendbaren Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls vielfach bekannt und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive Athylenoxidaddukte", Wiss. Veriagsgesell., Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Aufl. 1986.These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th Edition 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY , 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London. The necessary and usable formulation aids such as inert materials, surfactants, solvents and other additives are also widely known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen, " Introduction to Clay Colloid Chemistry "; 2nd Ed., J. Wiley & Sons, NY; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, NY 1963; McCutcheon's Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt, "Interface-active ethylene oxide adducts", Wiss. Veriagsgesellschaft., Stuttgart 1976; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix.Based on these formulations, combinations with other pesticidally active substances, e.g. Manufacture insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a finished formulation or as a tank mix.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykolethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt.Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or an inert substance, but also ionic and / or nonionic surfactants (wetting agents, dispersing agents), e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, sodium dibutylnaphthalene-sulfonic acid sodium or also contain sodium acid. To produce the wettable powders, the herbicidal active ingredients are finely ground, for example in conventional apparatus such as hammer mills, fan mills and air jet mills, and mixed at the same time or subsequently with the formulation auxiliaries.
Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calzium-Salze wie Ca-dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder Polyoxethylensorbitanester wie z.B. Polyoxyethylensorbitanfettsäureester.Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). As emulsifiers may be used, for example: calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan fatty acid such as Polyoxethylensorbitanester.
Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde.Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hergestellt werden.Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants, such as those e.g. already listed above for the other types of formulation.
Emulsionen, z.B. ÖI-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, herstellen.Emulsions, e.g. Oil-in-water emulsions (EW) can be used, for example, with stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as those e.g. already listed above for the other formulation types.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischern und Extrusion ohne festes Inertmaterial hergestellt. Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z.B. Verfahren in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57.Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylic acid or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers. Water-dispersible granules are generally produced using the customary methods, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material. For the production of plate, fluidized bed, extruder and spray granules, see, for example, the process in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961 , Seiten 81-96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103.For more details on the formulation of crop protection products see e.g. G.C. Klingman, "Weed Control as a Science," John Wiley and Sons, Inc., New York, 1961, pages 81-96, and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
Die agrochemischen Zubereitungen enthalten in der Regel 0,1 bis 99 Gew.-%, insbesondere 0,1 bis 95 Gew.-%, Wirkstoff der Formel (I).The agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active ingredient of the formula (I).
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0,05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-% .The active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight. Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient. In the case of water-dispersible granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating aids, fillers, etc. are used. The active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer und den pH-Wert und die Viskosität beeinflussende Mittel. Die Verbindungen der Formel (I) oder deren Salze können als solche oder in Form ihrer Zubereitungen (Formulierungen) mit anderen pestizid wirksamen Stoffen, wie z. B. Insektiziden, Akariziden, Nematiziden, Herbiziden, Fungiziden, Safenern, Düngemitteln und/oder Wachstumsregulatoren kombiniert eingesetzt werden, z. B. als Fertigformulierung oder als Tankmischungen. Als Kombinationspartner für die erfindungsgemäßen Wirkstoffe in Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetoiactat-Synthase, Acetyl- Coenzym-A-Carboxylase, PS I, PS II, HPPDO, Phytoene-Desaturase, Protoporphyrinogen-Oxidase, Glutamine-Synthetase, Cellulosebiosynthese, 5- Enolpyruvylshikimat-3-phosphat-Synthetase beruhen, einsetzbar. Solche Verbindungen und auch andere einsetzbare Verbindungen mit teilweise unbekanntem oder anderem Wirkungsmechanismus sind z.B. in Weed Research 26, 441-445 (1986), oder "The Pesticide Manual", 11. Auflage 1997 (im Folgenden auch kurz "PM") und 12. Auflage 2000, The British Crop Protection Council and the Royal Soc. of Chemistry (Herausgeber), und dort zitierter Literatur beschrieben. Als literaturbekannte Herbizide, die mit den Verbindungen der Formel (I) kombiniert werden können, sind z.B. folgende Wirkstoffe zu nennen (Anmerkung: Die Verbindungen sind entweder mit dem "common name" nach der international Organization for Standardization (ISO) oder mit dem chemischen Namen, ggf. zusammen mit einer üblichen Codenummer bezeichnet): acetochlor; acifluorfen(-sodium); aclonifen; AKH 7088, d.h. [[[1-[5-[2-Chloro-4- (trifluoromethyl)-phenoxy]-2-nitrophenyl]-2-methoxyethylidene]-amino]-oxy]- essigsäure und -essigsäuremethylester; alachlor; alloxydim(-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; amitrol; AMS, d.h. Ammoniumsulfamat; anilofos; asulam; atrazin; azafenidin, azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516 H, d.h. 5-Fluor-2-phenyl-4H-3,1-benzoxazin-4-on; beflubutamid, benazolin(-ethyl); benfluralin; benfuresate; bensulfuron(-methyl); bensulide; bentazone; benzobicyclon, benzofenap; benzofluor; benzoylprop(-ethyl); benzthiazuron; bialaphos; bifenox; bispyribac(-sodium), bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil, butamifos; butenachlor; buthidazole; butralin; butroxydim, butylate; cafenstrole (CH-900); carbetamide; carfentrazone(-ethyl) (ICI-A0051 ); caloxydim, CDAA, d.h. 2-Chlor-N,N-di-2-propenylacetamid; CDEC, d.h. Diethyldithiocarbaminsäure-2-chlorallylester; chlomethoxyfen; chloramben; chlorazifop-butyl, chlormesulon (ICI-A0051); chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron(-ethyl); chlomitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; chlortoluron, cinidon(-methyl und -ethyl), cinmethylin; cinosulfuron; clefoxydim, clethodim; clodinafop und dessen Esterderivate (z.B. clodinafop-propargyl); clomazone; clomeprop; cloproxydim; clopyralid; clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron (JC 940); cyanazine; cycloate; cyciosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop und dessen Esterderivate (z.B. Butylester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-D, 2,4-DB; 2,4-DB, dalapon; desmedipham; desmetryn; di-allate; dicamba; dichlobenil; dichlorprop; diclofop und dessen Ester wie diclofop-methyl; diclosulam, diethatyl(-ethyl); difenoxuron; difenzoquat; diflufenican; diflufenzopyr, dimefuron; dimepiperate, dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethazone, dimexyflam, dimethipin; dimetrasulfuron, dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, d.h. 5-Cyano-1 -(1 ,1 -dimethylethyl)-N-methyl-1 H-pyrazole-4-carboxamid; endothal; epoprodan, EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethidimuron; ethiozin; ethofumesate; ethoxyfen und dessen Ester (z.B. Ethylester, HN-252); ethoxysulfuron, etobenzanid (HW 52); F5231 , d.h. N-[2-Chlor-4-fluor-5-[4-(3- fluorpropyl)-4,5-dihydro-5-oxo-1 H-tetrazol-1-yl]-phenyl]-ethansulfonamid; fenoprop; fenoxan, fenoxaprop und fenoxaprop-P sowie deren Ester, z.B. fenoxaprop-P-ethyi und fenoxaprop-ethyl; fenoxydim; fentrazamide, fenuron; flamprop(-methyl oder -isopropyl oder -isopropyl-L); flazasulfuron; floazulate, florasulam, fluazifop und fluazifop-P und deren Ester, z.B. fluazifop-butyl und fluazifop-P-butyl; flucarbazone(- sodium), fluchloralin; flumetsulam; flumeturon; flumiclorac(-pentyl), flumioxazin (S- 482); flumipropyn; fluometuron, fluorochloridone, fluorodifen; fluoroglycofen(-ethyl); flupoxam (KNW-739); flupropacil (UBIC-4243); flupyrsulfuron(-methyl oder -sodium), flurenol(-butyl), fluridone; flurochloridone; fluroxypyr(-meptyl); flurprimidol, flurtamone; fluthiacet(-methyl), fluthiamide, fomesafen; foramsulfuron, fosamine; furyloxyfen; glufosinate(-ammonium); giyphosate(-isopropylammonium); halosafen; halosulfuron(-methyl) und dessen Ester (z.B. Methylester, NC-319); haloxyfop und dessen Ester; haloxyfop-P (= R-haloxyfop) und dessen Ester; hexazinone; imazamethabenz(-methyi); imazapyr; imazaquin und Salze wie das Ammoniumsalz; imazamethapyr, imazamox, imazapic, imazethamethapyr; imazethapyr; imazosulfuron; indanofan, ioxynil; isocarbamid; isopropalin; isoproturon; isouron; isoxaben; isoxachlortole, isoxaflutole, isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidid; mesosulfuron, mesotrione, metamitron; metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone; methyldymron; metabenzuron, methobenzuron; metobromuron; (alpha-)metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MH; molinate; monalide; monocarbamide dihydrogensulfate; monolinuron; monuron; MT 128, d.h. 6-Chlor-N-(3-chlor-2-propenyl)- 5-methy!-N-phenyl-3-pyridazinamin; MT 5950, d.h. N-[3-Chlor-4-(1-methylethyl)- phenyl]-2-methylpentanamid; naproanilide; napropamide; naptalam; NC 310, d.h. 4-(2,4-dichlorbenzoyl)-1 -methyl-5-benzyloxypyrazol; neburon; nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazon; oxasulfuron, oxaziclomefone, oxyfluorfen; paraquat; pebulate; pelargonic acid, pendimethalin; pentoxazone, perfluidone; phenisopham; phenmedipham; picloram; picolinafen, piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron(-methyl); procarbazone-(sodium), procyazine; prodiamine; profluralin; proglinazine(-ethyl); prometon; prometryn; propachlor; propanil; propaquizafop und dessen Ester; propazine; propham; propisochlor; propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor; pyraflufen(-ethyl), pyrazolinate; pyrazon; pyrazosulfuron(-ethyl); pyrazoxyfen; pyribenzoxim, pyributicarb, pyridafol, pyridate; pyrimidobac(-methyl), pyrithiobac(-sodium) (KIH-2031); pyroxofop und dessen Ester (z.B. Propargylester); quinclorac; quinmerac; quinoclamine, quinofop und dessen Esterderivate, quizalofop und quizalofop-P und deren Esterderivate z.B. quizalofop-ethyl; quizalofop-P-tefuryl und -ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, d.h. 2-[4-Chlor-2-fluor-5-(2- propynyloxy)-phenyl]-4,5,6,7-tetrahydro-2H-indazol; secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, d.h. 2-[[7-[2-Chlor-4-(trifluor-methyl)- phenoxy]-2-naphthalenyl]-oxy]rpropansäure und -methylester; sulcotrione, sulfentrazon (FMC-97285, F-6285); sulfazuron; sulfometuron(-methyl); sulfosate (ICI-A0224); sulfosulfuron, TCA; tebutam (GCP-5544); tebuthiuron; tepraloxydim, terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450, d.h. N,N-Diethyl-3-[(2-ethyl-6-methylphenyl)-sulfonyl]-1 H-1 ,2,4-triazol-1-carboxamid; thenylchlor (NSK-850); thiafluamide, thiazafluron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thifensulfuron(-methyl); thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triaziflam, triazofenamide; tribenuron(-methyl); triclopyr; tridiphane; trietazine; trifluralin; triflusulfuron und Ester (z.B. Methylester, DPX-66037); trimeturon; tritosulfuron, tsitodef; vernolate; WL 110547, d.h. 5-Phenoxy-1 -[3- (trifluormethyl)-phenyl]-1 H-tetrazol; BAY MKH 6561 , UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; DOWCO-535; DK- 8910; V-53482; PP-600; MBH-001 ; KIH-9201 ; ET-751 ; KIH-6127 und KIH-2023.In addition, the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity. The compounds of formula (I) or their salts can be used as such or in the form of their preparations (formulations) with other pesticidal substances, such as B. insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators can be used in combination, for. B. as a finished formulation or as a tank mix. As a combination partner for the active substances according to the invention in mixture formulations or in the tank mix, there are, for example, known active substances which are based on an inhibition of, for example, acetoiactate synthase, acetyl-coenzyme A carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen Oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase are used. Such compounds and also other usable compounds with a mechanism of action that is partly unknown or different are described, for example, in Weed Research 26, 441-445 (1986) or "The Pesticide Manual", 11th edition 1997 (hereinafter also referred to as "PM") and 12. Edition 2000, The British Crop Protection Council and the Royal Soc. of Chemistry (editor), and the literature cited there. Examples of herbicides known from the literature which can be combined with the compounds of the formula (I) are the following active ingredients (note: the compounds are either with the "common name" according to the international organization for standardization (ISO) or with the chemical name , possibly together with a usual code number): acetochlor; acifluorfen (-sodium); aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and methyl acetate; alachlor; alloxydim (-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; amitrol; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azafenidin, azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516 H, ie 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamide, benazolin (-ethyl); benfluralin; benfuresate; bensulfuron (-methyl); bensulide; bentazone; benzobicyclone, benzofenap; benzofluor; benzoylprop (-ethyl); benzthiazuron; bialaphos; bifenox; bispyribac (-sodium), bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil, butamifos; butenachlor; buthidazole; butraline; butroxydim, butylates; cafenstrole (CH-900); carbetamide; carfentrazone (-ethyl) (ICI-A0051); caloxydim, CDAA, ie 2-chloro-N, N-di-2-propenylacetamide; CDEC, ie 2-chloroallyl ester of diethyldithiocarbamic acid; chlomethoxyfen; chloramben; chlorazifop-butyl, chloromesulone (ICI-A0051); chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron (-ethyl); chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; chlorotoluron, cinidon (-methyl and -ethyl), cinmethylin; cinosulfuron; clefoxydim, clethodim; clodinafop and its ester derivatives (eg clodinafop-propargyl); clomazone; clomeprop; cloproxydim; clopyralid; clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron (JC 940); cyanazine; cycloate; cyciosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (eg butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-D, 2,4-DB; 2,4-DB, dalapon; desmedipham; Desmetryn; di-allate; dicamba; dichlobenil; dichloroprop; diclofop and its esters such as diclofop-methyl; diclosulam, diethatyl (ethyl); difenoxuron; difenzoquat; diflufenican; diflufenzopyr, dimefuron; dimepiperate, dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethazone, dimexyflam, dimethipin; dimetrasulfuron, dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, ie 5-cyano-1 - (1,1-dimethylethyl) -N-methyl-1H-pyrazole-4-carboxamide; endothal; epoprodan, EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; Ethidimuron; ethiozin; ethofumesate; ethoxyfen and its esters (eg ethyl ester, HN-252); ethoxysulfuron, etobenzanid (HW 52); F5231, ie N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1 H-tetrazol-1-yl] phenyl] ethanesulfonamide; fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters, for example fenoxaprop-P-ethyi and fenoxaprop-ethyl; fenoxydim; fentrazamide, fenuron; flamprop (-methyl or -isopropyl or -isopropyl-L); flazasulfuron; floazulate, florasulam, fluazifop and fluazifop-P and their esters, for example fluazifop-butyl and fluazifop-P-butyl; flucarbazone (- sodium), fluchloralin; flumetsulam; flumeturon; flumiclorac (pentyl), flumioxazin (S-482); flumipropyn; fluometuron, fluorochloridone, fluorodifen; fluoroglycofen (-ethyl); flupoxam (KNW-739); flupropacil (UBIC-4243); flupyrsulfuron (methyl or sodium), flurenol (butyl), fluridone; flurochloridone; fluroxypyr (-meptyl); flurprimidol, flurtamone; fluthiacet (methyl), fluthiamide, fomesafen; foramsulfuron, fosamine; furyloxyfen; glufosinate (-ammonium); giyphosate (-isopropylammonium); halo safen; halosulfuron (-methyl) and its esters (eg methyl ester, NC-319); haloxyfop and its esters; haloxyfop-P (= R-haloxyfop) and its esters; hexazinone; imazamethabenz (-methyl); imazapyr; imazaquin and salts such as the ammonium salt; imazamethapyr, imazamox, imazapic, imazethamethapyr; imazethapyr; imazosulfuron; indanofan, ioxynil; isocarbamid; isopropalin; isoproturon; isouron; isoxaben; isoxachlortole, isoxaflutole, isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidide; mesosulfuron, mesotrione, metamitron; metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone; methyldymron; metabenzuron, methobenzuron; metobromuron; (Alpha-) metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MH; molinate; monalide; monocarbamide dihydrogen sulfates; monolinuron; monuron; MT 128, ie 6-chloro-N- (3-chloro-2-propenyl) -5-methy! -N-phenyl-3-pyridazinamine; MT 5950, ie N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazon; oxasulfuron, oxaziclomefone, oxyfluorfen; paraquat; pebulate; pelargonic acid, pendimethalin; pentoxazone, perfluidone; phenisopham; phenmedipham; picloram; picolinafen, piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron (-methyl); procarbazone- (sodium), procyazine; prodi amines; profluralin; proglinazine (-ethyl); prometon; prometryne; propachlor; propanil; propaquizafop and its esters; propazine; propham; propisochlor; Propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor; pyraflufen (-ethyl), pyrazolinate; pyrazon; pyrazosulfuron (-ethyl); pyrazoxyfen; pyribenzoxim, pyributicarb, pyridafol, pyridate; pyrimidobac (-methyl), pyrithiobac (-sodium) (KIH-2031); pyroxofop and its esters (eg propargyl esters); quinclorac; quinmerac; quinoclamine, quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives, for example quizalofop-ethyl; quizalofop-P-tefuryl and ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, ie 2- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -4,5,6,7-tetrahydro-2H-indazole; secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, ie 2 - [[7- [2-chloro-4- (trifluoromethyl) - phenoxy] -2-naphthalenyl] -oxy] rpropanoic acid and methyl ester; sulcotrione, sulfentrazone (FMC-97285, F-6285); sulfazuron; sulfometuron (-methyl); sulfosate (ICI-A0224); sulfosulfuron, TCA; tebutam (GCP-5544); tebuthiuron; tepraloxydim, terbacil; terbucarb; terbuchlor; terbumeton; Terbuthylazine; terbutryn; TFH 450, ie N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1 H-1, 2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiafluamide, thiazafluron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thifensulfuron (-methyl); thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triaziflam, triazofenamide; tribenuron (-methyl); triclopyr; tridiphane; trietazine; trifluralin; triflusulfuron and esters (e.g. methyl ester, DPX-66037); trimeturon; tritosulfuron, tsitodef; vernolate; WL 110547, ie 5-phenoxy-1 - [3- (trifluoromethyl) phenyl] -1 H-tetrazole; BAY MKH 6561, UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; Dowco-535; DK-8910; V-53482; PP-600; MBH-001; KIH-9201; ET-751; KIH-6127 and KIH-2023.
Von besonderem Interesse ist die selektive Bekämpfung von Schadpflanzen in Kulturen von Nutz- und Zierpflanzen. Obgleich die erfindungsgemäßen Verbindungen (I) bereits in vielen Kulturen sehr gute bis ausreichende Selektivität aufweisen, können prinzipiell in einigen Kulturen und vor allem auch im Falle von Mischungen mit anderen Herbiziden, die weniger selektiv sind, Phytotoxizitäten an den Kulturpflanzen auftreten. Diesbezüglich sind Kombinationen erfindungsgemäßer Verbindungen (I) von besonderem Interesse, welche die Verbindungen (I) bzw. deren Kombinationen mit anderen Herbiziden oder Pestiziden und Safenern enthalten. Die Safener, welche in einem antidotisch wirksamen Gehalt eingesetzt werden, reduzieren die phytotoxischen Nebenwirkungen der eingesetzten Herbizide/Pestizide, z. B. in wirtschaftlich bedeutenden Kulturen wie Getreide (Weizen, Gerste, Roggen, Mais, Reis, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja, vorzugsweise Getreide. Folgende Gruppen von Verbindungen kommen beispielsweise als Safener für die Verbindungen (I) und deren Kombinationen mit weiteren Pestiziden in Frage:The selective control of harmful plants in crops of useful and ornamental plants is of particular interest. Although the compounds (I) according to the invention already have very good to sufficient selectivity in many crops, phytotoxicity can occur on the crop plants in principle in some crops and especially in the case of mixtures with other herbicides which are less selective. In this regard, combinations of compounds (I) according to the invention which contain the compounds (I) or their combinations with other herbicides or pesticides and safeners are of particular interest. The safeners, which are used in an antidotically effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, eg. B. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soy, preferably cereals. The following groups of compounds are suitable, for example, as safeners for the compounds (I) and their combinations with other pesticides:
a) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure, vorzugsweise Verbindungen wie 1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3- carbonsäureethylester (S1-1) ("Mefenpyr-diethyl", PM, S. 781-782), und verwandte Verbindungen, wie sie in der WO 91/07874 beschrieben sind, b) Derivate der Dichlorphenylpyrazolcarbonsäure, vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-methyl-pyrazol-3-carbonsäureethylester (S1 -2), 1-(2,4-Dichlorphenyl)-5-isopropyl-pyrazol-3-carbonsäureethyIester (S1-3), 1-(2,4-Dichlorphenyl)-5-(1 ,1-dimethyl-ethyl)pyrazol-3-carbonsäureethyl-ester (S1 -4), 1 -(2,4-Dichlorphenyl)-5-phenyl-pyrazol-3-carbonsäureethylester (S1 -5) und verwandte Verbindungen, wie sie in EP-A-333 131 und EP-A-269 806 beschrieben sind. c) Verbindungen vom Typ der Triazolcarbonsäuren, vorzugsweise Verbindungen wie Fenchlorazol(-ethylester), d.h. 1-(2,4-Dichlorphenyl)-5-trichlormethyl-(1 H)-1 ,2,4-triazol-3- carbonsäureethylester (S1-6), und verwandte Verbindungen (siehe EP-A-174 562 und EP-A-346 620); d) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure, oder der 5,5-Diphenyl-2-isoxazolin-3-carbonsäure vorzugsweise Verbindungen wie 5-(2,4-Dichlorbenzyl)-2-isoxazolin-3-carbonsäureethylester (S1-7) oder 5-Phenyl-2-isoxazolin-3-carbonsäureethylester (S1-8) und verwandte Verbindungen, wie sie in WO 91/08202 beschrieben sind, bzw. der 5,5-Diphenyl-2-isoxazolin-carbonsäureethylester (S1-9) ("Isoxadifen-ethyl") oder -n-propylester (S1-10) oder der 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin- 3-carbonsäureethylester (S1-11 ), wie sie in der deutschen Patentanmeldung (WO-A-95/07897) beschrieben sind. e) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2), vorzugsweise (5-Chlor-8-chinolinoxy)-essigsäure-(1 -methyl-hex-1 -yl)-ester (Common name "Cloquintocet-mexyl" (S2-1) (siehe PM, S. 263-264) (5-Chlor-8-chinolinoxy)-essigsäure-(1 ,3-dimethyl-but-1 -yl)-ester (S2-2), (5-Chlor-8-chinolinoxy)-essigsäure-4-allyl-oxy-butylester (S2-3), (5-Chlor-8-chinolinoxy)-essigsäure-1-allyloxy-prop-2-ylester (S2-4), (5-Chlor-8-chinolinoxy)-essigsäureethylester (S2-5), (5-Chlor-8-chinolinoxy)-essigsäuremethyiester (S2-6), (5-Chlor-8-chinolinoxy)-essigsäureallylester (S2-7),a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type, preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (S1-1) ("Mefenpyr-diethyl", PM, pp. 781-782), and related Compounds as described in WO 91/07874, b) derivatives of dichlorophenylpyrazole carboxylic acid, preferably compounds such as 1 - (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylic acid ethyl ester (S1 -2), 1- ( 2,4-dichlorophenyl) -5-isopropyl-pyrazole-3-carboxylic acid ethyl ester (S1-3), 1- (2,4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (S1 -4), 1 - (2,4-dichlorophenyl) -5-phenyl-pyrazole-3-carboxylic acid ethyl ester (S1 -5) and related compounds as described in EP-A-333 131 and EP-A-269 806 are described. c) Compounds of the triazole carboxylic acid type, preferably compounds such as fenchlorazole (ethyl ester), ie 1- (2,4-dichlorophenyl) -5-trichloromethyl- (1 H) -1, 2,4-triazole-3-carboxylic acid ethyl ester (S1 -6), and related compounds (see EP-A-174 562 and EP-A-346 620); d) Compounds of the 5-benzyl or 5-phenyl-2-isoxazoline-3-carboxylic acid type, or the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid, preferably compounds such as 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (S1-7) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-8) and related compounds, as described in WO 91/08202, or 5.5 -Diphenyl-2-isoxazoline-carboxylic acid ethyl ester (S1-9) ("isoxadifen-ethyl") or -n-propyl ester (S1-10) or the 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3- carboxylic acid ethyl ester (S1-11), as described in the German patent application (WO-A-95/07897). e) Compounds of the 8-quinolinoxyacetic acid (S2) type, preferably (5-chloro-8-quinolinoxy) acetic acid (1-methyl-hex-1-yl) ester (common name "Cloquintocet-mexyl" (S2- 1) (see PM, pp. 263-264) (5-chloro-8-quinolinoxy) -acetic acid- (1,3-dimethyl-but-1-yl) ester (S2-2), (5-chloro 8-quinolinoxy) -acetic acid-4-allyl-oxy-butyl ester (S2-3), (5-chloro-8-quinolinoxy) -acetic acid-1-allyloxy-prop-2-yl ester (S2-4), (5- Chloro-8-quinolinoxy) -acetic acid ethyl ester (S2-5), (5-chloro-8-quinolinoxy) -acetic acid methyl ester (S2-6), (5-chloro-8-quinolinoxy) allyl acetate (S2-7),
(5-Chlor-8-chinolinoxy)-essigsäure-2-(2-propyliden-iminoxy)-1- ethylester (S2-8),(5-chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (S2-8),
(5-Chlor-8-chinolinoxy)-essigsäure-2-oxo-prop-1 -ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86 750, EP-A-94 349 und(5-Chloro-8-quinolinoxy) -acetic acid-2-oxo-prop-1-ethyl ester (S2-9) and related compounds as described in EP-A-86 750, EP-A-94 349 and
EP-A-191 736 oder EP-A-0 492 366 beschrieben sind. f) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)-malonsäure, vorzugsweise Verbindungen wie (5-Chlor-8-chinolinoxy)-malonsäure- diethylester, (5-Chlor-8-chinolinoxy)-malonsäurediallylester, (5-Chlor-8-chinolinoxy)-malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind. g) Wirkstoffe vom Typ der Phenoxyessig- bzw. -propionsäurederivate bzw. der aromatischen Carbonsäuren, wie z.B. 2,4-Dichlorphenoxyessigsäure(ester) (2,4-D), 4-Chlor-2-methyl-phenoxy-propionester (Mecoprop), MCPA oder 3,6-Dichlor-2-methoxy-benzoesäure(ester) (Dicamba). h) Wirkstoffe vom Typ der Pyrimidine, die als bodenwirksame Safener in Reis angewendet werden, wie z. B.EP-A-191 736 or EP-A-0 492 366. f) Compounds of the type of (5-chloro-8-quinolinoxy) malonic acid, preferably compounds such as (5-chloro-8-quinolinoxy) malonic acid diethyl ester, (5-chloro-8-quinolinoxy) malonic acid diallyl ester, (5- Chloro-8-quinolinoxy) -malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198. g) active substances of the phenoxyacetic or propionic acid derivative or aromatic carboxylic acid type, e.g. 2,4-dichlorophenoxyacetic acid (ester) (2,4-D), 4-chloro-2-methylphenoxy-propionester (mecoprop), MCPA or 3,6-dichloro-2-methoxy-benzoic acid (ester) (dicamba) , h) Active substances of the pyrimidine type, which are used as soil-active safeners in rice, such as, for. B.
"Fenclorim" (PM, S. 512-511) (= 4,6-Dichlor-2-phenylpyrimidin), das als"Fenclorim" (PM, pp. 512-511) (= 4,6-dichloro-2-phenylpyrimidine), which as
Safener für Pretilachlor in gesätem Reis bekannt ist, i) Wirkstoffe vom Typ der Dichloracetamide, die häufig als VorauflaufsafenerSafeners known for pretilachlor in sown rice are i) active substances of the dichloroacetamide type, often used as pre-emergence safeners
(bodenwirksame Safener) angewendet werden, wie z. B.(Soil-effective safeners), such as B.
"Dichlormid" (PM, S. 363-364) (= N,N-Diallyl-2,2-dichloracetamid),"Dichlormid" (PM, pp. 363-364) (= N, N-diallyl-2,2-dichloroacetamide),
"R-29148" (= 3-Dichloracetyl-2,2,5-trimethyl-1 ,3-oxazolidin von der Firma"R-29148" (= 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine from the company
Stauffer),Stauffer)
"Benoxacor" (PM, S. 102-103) (= 4-Dichloracetyl-3,4-dihydro-3-methyl-2H-1 ,4- benzoxazin)."Benoxacor" (PM, pp. 102-103) (= 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine).
"PPG-1292" (= N-Allyl-N-[(1 ,3-dioxolan-2-yl)-methyl]-dichloracetamid von der"PPG-1292" (= N-allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide from the
Firma PPG Industries),PPG Industries),
"DK-24" (= N-Allyl-N-[(allylaminocarbonyl)-methyl]-dichloracetamid von der"DK-24" (= N-allyl-N - [(allylaminocarbonyl) methyl] dichloroacetamide from the
Firma Sagro-Chem),Sagro-Chem),
"AD-67" oder "MON 4660" (= 3-Dichloracetyl-1-oxa-3-aza-spiro[4,5]decan von der Firma Nitrokemia bzw. Monsanto), "Diclonon" oder "BAS145138" oder "LAB145138" (= (= 3-Dichloracetyl-2,5,5- trimethyl-1 ,3-diazabicyclo[4.3.0]nonan von der Firma BASF) und"AD-67" or "MON 4660" (= 3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane from Nitrokemia or Monsanto), "Diclonon" or "BAS145138" or "LAB145138" (= (= 3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo [4.3.0] nonane from BASF) and
"Furilazol" oder "MON 13900" (siehe PM, 637-638) (= (RS)-3-Dichloracetyl-5-"Furilazole" or "MON 13900" (see PM, 637-638) (= (RS) -3-dichloroacetyl-5-
(2-furyl)-2,2-dimethyloxazolidin) j) Wirkstoffe vom Typ der Dichloracetonderivate, wie z. B.(2-furyl) -2,2-dimethyloxazolidine) j) active substances of the dichloroacetone derivative type, such as, for. B.
"MG 191" (CAS-Reg. Nr. 96420-72-3) (= 2-Dichlormethyl-2-methyl-1 ,3- dioxolan von der Firma Nitrokemia), das als Safener für Mais bekannt ist, k) Wirkstoffe vom Typ der Oxyimino-Verbindungen, die als Saatbeizmittel bekannt sind, wie z. B."MG 191" (CAS Reg. No. 96420-72-3) (= 2-dichloromethyl-2-methyl-1,3-dioxolane from the company Nitrokemia), which is known as a safener for corn, k) active substances from Type of oxyimino compounds known as seed dressings, such as. B.
"Oxabetrinil" (PM, S. 902-903) (= (Z)-1 ,3-Dioxolan-2- ylmethoxyimino(phenyl)acetonitril), das als Saatbeiz-Safener für Hirse gegen"Oxabetrinil" (PM, pp. 902-903) (= (Z) -1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile), which acts as a seed dressing safener for millet against
Schäden von Metolachlor bekannt ist,Known damage from metolachlor
"Fluxofenim" (PM, S. 613-614) (= 1-(4-Chlorphenyl)-2,2,2-trifluor-1-ethanon-"Fluxofenim" (PM, pp. 613-614) (= 1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-
0-(1 ,3-dioxolan-2-ylmethyl)-oxim, das als Saatbeiz-Safener für Hirse gegen0- (1, 3-dioxolan-2-ylmethyl) oxime, which acts as a seed dressing safener for millet against
Schäden von Metolachlor bekannt ist, undKnown damage from metolachlor, and
"Cyometrinil" oder "-CGA-43089" (PM, S. 1304) (= (Z)-"Cyometrinil" or "-CGA-43089" (PM, p. 1304) (= (Z) -
Cyanomethoxyimino(phenyl)acetonitril), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, I) Wirkstoffe vom Typ der Thiazolcarbonsäureester, die als Saatbeizmittel bekannt sind, wie z. B.Cyanomethoxyimino (phenyl) acetonitrile), which is known as a seed dressing safener for millet against damage to metolachlor, I) active substances of the thiazole carboxylic acid ester type, which are known as seed dressings, such as, for. B.
"Flurazol" (PM, S. 590-591) (= 2-Chlor-4-trifluormethyl-1 ,3-thiazol-5- carbonsäurebenzylester), das als Saatbeiz-Safener für Hirse gegen Schäden von Alachlor und Metolachlor bekannt ist, m) Wirkstoffe vom Typ der Naphthalindicarbonsäurederivate, die als"Flurazole" (PM, p. 590-591) (= 2-chloro-4-trifluoromethyl-1, 3-thiazole-5-carboxylic acid benzyl ester), which is known as a seed dressing safener for millet against damage to alachlor and metolachlor, m ) Active substances of the type of naphthalenedicarboxylic acid derivatives, which as
Saatbeizmittel bekannt sind, wie z. B.Seed dressings are known, such as. B.
"Naphthalic anhydrid" (PM, S. 1342) (= 1 ,8-"Naphthalic anhydride" (PM, p. 1342) (= 1, 8-
Naphthalindicarbonsäureanhydrid), das als Saatbeiz-Safener für Mais gegenNaphthalenedicarboxylic anhydride), which acts as a seed dressing safener against corn
Schäden von Thiocarbamatherbiziden bekannt ist, n) Wirkstoffe vom Typ Chromanessigsäurederivate, wie z. B.Damage of thiocarbamate herbicides is known, n) active substances of the chromanacetic acid derivative type, such as. B.
"CL 304415" (CAS-Reg. Nr. 31541-57-8) (= 2-(4-Carboxy-chroman-4-yl)- essigsäure von der Firma American Cyanamid), das als Safener für Mais gegen Schäden von Imidazolinonen bekannt ist, o) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen wie Reis aufweisen, wie z. B. "Dimepiperate" oder "MY-93" (PM, S. 404-405) (= Piperidin-1- thiocarbonsäure-S-1-methyl-1-phenylethylester), das als Safener für Reis gegen Schäden des Herbizids Molinate bekannt ist,"CL 304415" (CAS Reg. No. 31541-57-8) (= 2- (4-carboxy-chroman-4-yl) - acetic acid from American Cyanamid), which acts as a safener for maize against damage to imidazolinones is known o) active substances which, in addition to a herbicidal action against harmful plants, also have a safener action on crop plants such as rice, such as, for. B. "Dimepiperate" or "MY-93" (PM, pp. 404-405) (= piperidine-1-thiocarboxylic acid S-1-methyl-1-phenylethyl ester), which is known as a safener for rice against damage to the herbicide Molinate is
"Daimuron" oder "SK 23" (PM, S. 330) (= 1-(1-Methyl-1-phenylethyl)-3-p-tolyl- hamstoff), das als Safener für Reis gegen Schäden des Herbizids Imazosulfuron bekannt ist,"Daimuron" or "SK 23" (PM, p. 330) (= 1- (1-methyl-1-phenylethyl) -3-p-tolylurea), which is known as a safener for rice against damage to the herbicide imazosulfuron .
"Cumyluron" = "JC-940" (= 3-(2-Chlorphenylmethyl)-1-(1-methyl-1-phenyl- ethyl)-harnstoff, siehe JP-A-60087254), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist,"Cumyluron" = "JC-940" (= 3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) urea, see JP-A-60087254), which acts as a safener for rice against damage some herbicides is known
"Methoxyphenon" oder "NK 049" (= 3,3'-Dimethyl~4-methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "CSB" (= 1-Brom-4-(chlormethylsulfonyl)-benzol) (CAS-Reg. Nr. 54091-06-4 von Kumiai), das als Safener gegen Schäden einiger Herbizide in Reis bekannt ist, p) N-Acylsulfonamide der Formel (S3) und ihre Salze,"Methoxyphenon" or "NK 049" (= 3,3'-dimethyl ~ 4-methoxy-benzophenone), which is known as a safener for rice against damage by some herbicides, "COD" (= 1-bromo-4- (chloromethylsulfonyl) -benzene) (CAS Reg. No. 54091-06-4 from Kumiai), which is known as a safener against damage to some herbicides in rice, p) N-acylsulfonamides of the formula (S3) and their salts,
wie sie in WO-A-97/45016 beschrieben sind, as described in WO-A-97/45016,
q) Acylsulfamoylbenzoesäureamide der allgemeinen Formel (S4), gegebenenfalls auch in Salzform,q) acylsulfamoylbenzoic acid amides of the general formula (S4), optionally also in salt form,
wie sie in der Internationalen Anmeldung Nr. PCT/EP98/06097 beschrieben sind, und r) Verbindungen der Formel (S5), as described in International Application No. PCT / EP98 / 06097, and r) compounds of the formula (S5),
wie sie in der WO-A 98/13 361 beschrieben sind, einschließlich der Stereoisomeren und den in der Landwirtschaft gebräuchlichen Salzen.as described in WO-A 98/13 361, including the stereoisomers and the salts customary in agriculture.
Von besonderem Interesse sind unter den genannten Safenern sind (S1-1) und (S1-Of particular interest among the safeners mentioned are (S1-1) and (S1-
9) und (S2-1), insbesondere (S1-1) und (S1-9).9) and (S2-1), in particular (S1-1) and (S1-9).
Einige der Safener sind bereits als Herbizide bekannt und entfalten somit neben derSome of the safeners are already known as herbicides and therefore develop alongside
Herbizidwirkung bei Schadpflanzen zugleich auch Schutzwirkung bei denHerbicidal activity in harmful plants also protective effect in the
Kulturpflanzen.Crops.
Die Gewichtsverhältnisse von Herbizid(mischung) zu Safener hängt im Allgemeinen von der Aufwandmenge an Herbizid und der Wirksamkeit des jeweiligen Safeners ab und kann innerhalb weiter Grenzen variieren, beispielsweise im Bereich von 200:1 bis 1 :200, vorzugsweise 100:1 bis 1 :100, insbesondere 20:1 bis 1 :20. Die Safener können analog den Verbindungen (I) oder deren Mischungen mit weiteren Herbiziden/Pestiziden formuliert werden und als Fertigformulierung oder Tankmischung mit den Herbiziden bereitgestellt und angewendet werden.The weight ratio of herbicide (mixture) to safener generally depends on the amount of herbicide applied and the effectiveness of the particular safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20. The safeners can be formulated analogously to the compounds (I) or their mixtures with further herbicides / pesticides and can be provided and used as a finished formulation or tank mixture with the herbicides.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Herbizid- oder Herbizid-Safener-Formulierungen gegebenenfalls in üblicher weise verdünnt z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids, u.a. variiert die erforderliche Aufwandmenge der Verbindungen der Formel (I). Sie kann innerhalb weiter Grenzen schwanken, z.B. zwischen 0,001 und 10,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,005 und 5 kg/ha, insbesondere 0,01 und 3 kg/ha.For use, the herbicide or herbicide safener formulations present in commercial form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, using water. Preparations in the form of dust, ground granules or scattering granules and sprayable solutions are usually no longer diluted with other inert substances before use. The required application rate of the compounds of formula (I) varies with the external conditions, such as temperature, humidity, the type of herbicide used, and others. It can vary within wide limits, for example between 0.001 and 10.0 kg / ha or more of active substance, but is preferably between 0.005 and 5 kg / ha, in particular 0.01 and 3 kg / ha.
In den folgenden Beispielen beziehen sich Mengenangaben (auch Prozentangaben) auf das Gewicht, sofern nichts anderes speziell angegeben ist.In the following examples, quantities (also percentages) relate to the weight, unless specifically stated otherwise.
A. Chemische BeispieleA. Chemical examples
Beispiel A1Example A1
2-Dimethylaminomethylenamino-4-(1 -fluor-1 -methylethyl)-6-(1 - cyclopropyl-4-phenyl-1-butylamino)-1 ,3,5-triazin2-Dimethylaminomethyleneamino-4- (1-fluoro-1-methylethyl) -6- (1 - cyclopropyl-4-phenyl-1-butylamino) -1, 3,5-triazine
(siehe Tabelle 8, Beispiel 8-2)(see table 8, example 8-2)
Eine Lösung aus 1 ,71 g (5 mmol) 2-Amino-4-(1-fluor-1-methylethyl)-6-(1-cyciopropyl- 4-phenyl-1-butylamino)-1 ,3,5-triazin und 2 ml N,N-Dimethyl-formamid-dimethylacetal in 30 ml Toluol wird 2 h am Rückfluß gekocht. Anschließend werden alle flüchtigen Bestandteile sorgfältig abdestilliert. Man erhält 1 ,94 g (97,5 % der Theorie) 2- Dimethylaminomethylenamino-4-(1 -fluor-1 -methylethyl)-6-(1 -cyclopropyl-4-phenyl-1 - butylamino)-1 ,3,5-triazin als farbloses Öl.A solution of 1.71 g (5 mmol) of 2-amino-4- (1-fluoro-1-methylethyl) -6- (1-cyciopropyl-4-phenyl-1-butylamino) -1,3,5-triazine and 2 ml of N, N-dimethyl-formamide-dimethylacetal in 30 ml of toluene is boiled under reflux for 2 h. Then all volatile constituents are carefully distilled off. 1.94 g (97.5% of theory) of 2-dimethylaminomethyleneamino-4- (1-fluoro-1-methylethyl) -6- (1-cyclopropyl-4-phenyl-1-butylamino) -1, 3 are obtained. 5-triazine as a colorless oil.
Beispiel A2Example A2
N-[4-(1-Fluor-1-methylethyl)-6-(1-cyclopropyl-4-phenyl-1-butylamino)- ,3,5-triazin-2-yl]-formamidoxim (siehe Tabelle 8, Beispiel 8-27)N- [4- (1-Fluoro-1-methylethyl) -6- (1-cyclopropyl-4-phenyl-1-butylamino) -, 3,5-triazin-2-yl] -formamidoxime (see Table 8, example 8-27)
Zu einer Lösung aus 1 ,99 g (5 mmol) 2-Dimethylamino-methylenamino-4-(1-fluor-1- methylethyl)-6-(1-cyclopropyl-4-phenyl-1-butylamino)-1 ,3,5-triazin in 20 ml Methanol werden unter Rühren bei Raumtemperatur 0,69 g (10 mmol) Hydroxylamin Hydrochlorid gegeben. Die Reaktionsmischung wird 2 h bei Raumtemperatur gerührt. Es werden alle flüchtigen Bestandteile sorgfältig abdestilliert. Das Rohprodukt wird in Methylenchlorid aufgenommen. Es wird mit Wasser gewaschen, über Na2SO4 getrocknet und im Vakuum eingedampft. Man erhält 1 ,81 g (93,7 % der Theorie) N-[4-(1 -Fluor- 1 -methylethyl)-6-(1 -cyclopropyl-4-phenyl-1 -butylamino)-1 ,3,5- triazin-1-yl]-formamidoxim als gelbliches Öl.To a solution of 1.99 g (5 mmol) of 2-dimethylamino-methylenamino-4- (1-fluoro-1-methylethyl) -6- (1-cyclopropyl-4-phenyl-1-butylamino) -1, 3, 5-triazine in 20 ml of methanol are added with stirring at room temperature to 0.69 g (10 mmol) of hydroxylamine hydrochloride. The reaction mixture is 2 h at room temperature touched. All volatile components are carefully distilled off. The crude product is taken up in methylene chloride. It is washed with water, dried over Na 2 SO 4 and evaporated in vacuo. 1.81 g (93.7% of theory) of N- [4- (1-fluoro-1-methylethyl) -6- (1-cyclopropyl-4-phenyl-1-butylamino) -1, 3.5 are obtained - triazin-1-yl] -formamidoxime as a yellowish oil.
Beispiel A3Example A3
2-(4-Chlor-benzylidenamino)-4-(1 -fluor-1 -methylethyl)-6-(1 -cyclopropyl- 4-phenyl-1-butylamino)-1 ,3,5-triazin (siehe Tabelle 8, Beispiel 8-37)2- (4-chloro-benzylidenamino) -4- (1-fluoro-1-methylethyl) -6- (1 -cyclopropyl-4-phenyl-1-butylamino) -1, 3,5-triazine (see Table 8, Example 8-37)
Eine Mischung aus 2,5 g (7,28 mmol) 2-Amino-4-(1-fluor-1-methylethyl)-6-(1- cyclopropyl-4-phenyl-1-butylamino)-1 ,3,5-triazin, 1 ,08 g (7,70 mmol) p- Chlorbenzaldehyd und 100 mg p-Toluolsulfonsäure in 80 ml Toluol werden 10 h am Wasserabscheider gekocht. Nach Abkühlen werden alle flüchtigen Bestandteile abdestilliert. Das Rohprodukt wird mit Säulenchromatographie gereinigt (Laufmittel: Toluol/Ethylacetat = 85:15). Man erhält 3,0 g (89 % der Theorie) 2-(4-Chlor-6- benzylidenamino)-4-(1 -fluoro-1 -methylethyl)-6-(1 -cyclopropyl-4-phenyl-1 - butylamino)-1 ,3,5-triazin als farbloses Öl.A mixture of 2.5 g (7.28 mmol) of 2-amino-4- (1-fluoro-1-methylethyl) -6- (1-cyclopropyl-4-phenyl-1-butylamino) -1, 3.5 triazine, 1.08 g (7.70 mmol) of p-chlorobenzaldehyde and 100 mg of p-toluenesulfonic acid in 80 ml of toluene are boiled on a water separator for 10 h. After cooling, all volatile constituents are distilled off. The crude product is purified by column chromatography (eluent: toluene / ethyl acetate = 85:15). 3.0 g (89% of theory) of 2- (4-chloro-6-benzylidenamino) -4- (1-fluoro-1-methylethyl) -6- (1-cyclopropyl-4-phenyl-1-butylamino) are obtained ) -1, 3,5-triazine as a colorless oil.
Die in den nachfolgenden Tabellen 1 bis 12 beschriebenen Verbindungen erhält man gemäß oder analog zu den vorstehenden Beispielen A1 bis A3 oder den weiter oben allgemein beschriebenen Methoden. In den Tabellen bedeuten:The compounds described in Tables 1 to 12 below are obtained in accordance with or analogously to Examples A1 to A3 above or the methods generally described above. In the tables mean:
Abkürzungen:Abbreviations:
Me = MethylMe = methyl
Et EthylEt ethyl
Pr Propyl i-Pr = Isopropyl c-Pr = Cyclopropyl c-Bu = Cyclobutyl t-Bu = tertiär-Butyl c-Hexyl = Cyclohexyl Pr propyl i-Pr = isopropyl c-Pr = cyclopropyl c-Bu = cyclobutyl t-Bu = tertiary butyl c-hexyl = cyclohexyl
Ph = PhenylPh = phenyl
Bz = BenzylBz = benzyl
A2 = (CH2)2 = -CH2CH2-A2 = (CH 2 ) 2 = -CH 2 CH 2 -
A3 = (CH2)3 = -CH2CH2CH2-A3 = (CH 2 ) 3 = -CH 2 CH 2 CH 2 -
A4 = (CH2)4 = -CH2CH2CH2CH2-A4 = (CH 2 ) 4 = -CH 2 CH 2 CH 2 CH 2 -
Ac = COCH3 = AcetylAc = COCH 3 = acetyl
Ox = Oxiranyl Ox = oxiranyl
Ph = PhenylPh = phenyl
(X)n = "-" entspricht : n = = 0(X) n = "-" corresponds to: n = = 0
Die nachfolgenden Tabellen 1 bis 11 beziehen sich auf die allgemeine Formel (I), worin L° = eine direkte Bindung und R4 = Wasserstoffatom bedeuten:Tables 1 to 11 below relate to the general formula (I), in which L ° = a direct bond and R 4 = hydrogen atom:
Tabelle 1Table 1
Tabelle 2Table 2
σσ
--
0000
00
0 0
Tabelle 3Table 3
0 K0 K
00
00
4ϊ4ϊ
0000
00
0000
0 00 0
0 s 0 s
Tabelle 4Table 4
sO o so or not
Tabelle 5Table 5
sΩsΩ
tt
COCO
Tabelle 6Table 6
Tabelle 7Table 7
σ σ
Tabelle 8Table 8
ss
s 0s 0
s ss s
Tabelle 9 o oTable 9 o o
Tabelle 10Table 10
Tabellentables
t t
Tabelle 12: Verbindungen der FormelTable 12: Compounds of the formula
oO
B. FormulierungsbeispieleB. Examples of formulation
a) Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile einer Verbindung der Formel (I) und 90 Gew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert.a) A dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as an inert substance and comminuting in a hammer mill.
b) Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gewichtsteile einer Verbindung der Formel (I), 64 Gewichtsteile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyitaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt.b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyitauric acid sodium as wetting and dispersing agent and grind in a pin mill.
c) Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gewichtsteile einer Verbindung der Formel (I) mit 6 Gew.- Teilen Alkylphenolpolyglykolether (©Triton X 207), 3 Gew.-Teilen Isotridecanolpolyglykolether (8 EO) und 71 Gew.-Teilen paraffinischem Mineralöl (Siedebereich z.B. ca. 255 bis über 277°C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt.c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (© Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight. Parts of paraffinic mineral oil (boiling range e.g. approx. 255 to above 277 ° C) and ground in a friction ball mill to a fineness of less than 5 microns.
d) Ein emulgierbares Konzentrat wird erhalten aus 15 Gew.-Teilen einer Verbindung der Formel (I), 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen oxethyliertes Nonylphenol als Emulgator.d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
e) Ein in Wasser dispergierbares Granulat wird erhalten indem man 75 Gewichtsteile einer Verbindung der Formel (I),e) Water-dispersible granules are obtained by adding 75 parts by weight of a compound of the formula (I),
10 " ligninsulfonsaures Calcium,10 "calcium lignosulfonic acid,
5 " Natriumlaurylsulfat,5 "sodium lauryl sulfate,
3 " Polyvinylalkohol und3 "polyvinyl alcohol and
7 " Kaolin mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch7 "kaolin mixes, grinds on a pin mill and the powder in a fluid bed
Aufsprühen von Wasser als Granulierflüssigkeit granuliert.Spraying water granulated as granulating liquid.
f) Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man 25 Gewichtsteile einer Verbindung der Formel (I),f) A water-dispersible granulate is also obtained by 25 parts by weight of a compound of the formula (I),
5 " 2,2,-dinaphthylmethan-6,6'-disulfonsaures Natrium5 "2,2 , -dinaphthylmethane-6,6'-disulfonic acid sodium
2 " oleoylmethyitaurinsaures Natrium,2 "oleoylmethyitauric acid sodium,
1 Gewichtsteil Polyvinylalkohol,1 part by weight of polyvinyl alcohol,
17 Gewichtsteile Calciumcarbonät und17 parts by weight of calcium carbonate and
50 " Wasser auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet.Homogenize 50 "water on a colloid mill and pre-crush it, then grind it on a bead mill and atomize and dry the suspension thus obtained in a spray tower using a single-component nozzle.
C. Biologische BeispieleC. Biological examples
1. Unkrautwirkung im Vorauflauf1. Pre-emergence weed action
Samen bzw. Rhizomstücke von mono- und dikotylen Unkrautpflanzen werden in Plastiktöpfen in sandiger Lehmerde ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern oder Emulsionskonzentraten formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw. Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha in unterschiedlichen Dosierungen auf die Oberfläche der Abdeckerde appliziert.Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants are placed in sandy loam in plastic pots and covered with soil. The compounds according to the invention formulated in the form of wettable powders or emulsion concentrates are then applied as an aqueous suspension or emulsion with a water application rate of the equivalent of 600 to 800 l / ha in different dosages to the surface of the covering earth.
Nach der Behandlung werden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Unkräuter gehalten. Die optische Bonitur der Pflanzen- bzw. Auflaufschäden erfolgt nach dem Auflaufen der Versuchspflanzen nach einer Versuchszeit von 3 bis 4 Wochen im Vergleich zu unbehandelten Kontrollen.After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the weeds. After the test plants have emerged, the optical damage to the plants or the emergence damage is assessed after a test period of 3 to 4 weeks in comparison to untreated controls.
Die erfindungsgemäßen Verbindungen zeigen eine sehr gute Vorauflaufwirksamkeit gegen ein breites Spektrum von Ungräsem und Unkäutern. Beispielsweise werden Schadpflanzen wie Stellaria media, Lolium multiforum, Amaranthus retroflexus, Sinapis alba, Avena sativa und Setaria viridis von erfindungsgemäßen Verbindungen (siehe Beispiele A1 bis A3 und Verbindungen 2-1, 2-35, 2-36, 2-45, 2-55, 2-56, 3-1 , 3-14, 3-25, 3-37, 3-38, 3-40, 3-41 , 3-43, 3-44, 3-46, 3-47, 3-55, 3-56, 3-58, 3-59, 3-67, 3-68, 3-70, 3-71 , 3-74, 3-85, 3-86, 3-124, 5-1 , 5-40, 8-2, 8-11 , 8-20, 8-21, 8-27 und 8-37 aus Tabellen 1 bis 12) im Vorauflaufverfahren sehr gut bekämpft.The compounds according to the invention show a very good pre-emergence activity against a broad spectrum of grasses and weeds. For example, harmful plants such as Stellaria media, Lolium multiforum, Amaranthus retroflexus, Sinapis alba, Avena sativa and Setaria viridis are used by compounds according to the invention (see examples A1 to A3 and connections 2-1, 2-35, 2-36, 2-45, 2-55, 2-56, 3-1, 3-14, 3-25, 3-37, 3- 38, 3-40, 3-41, 3-43, 3-44, 3-46, 3-47, 3-55, 3-56, 3-58, 3-59, 3-67, 3-68, 3-70, 3-71, 3-74, 3-85, 3-86, 3-124, 5-1, 5-40, 8-2, 8-11, 8-20, 8-21, 8- 27 and 8-37 from Tables 1 to 12) very well combated in the pre-emergence process.
2. Unkrautwirkung im Nachauflauf2. Post-emergence weed action
Samen bzw. Rhizomstücke von mono- und dikotylen Unkräutern werden in Plastiktöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. Drei Wochen nach der Aussaat werden die Versuchspflanzen im Dreiblattstadium behandelt. Die als Spritzpulver bzw. als Emulsionskonzentrate formulierten erfindungsgemäßen Verbindungen werden in verschiedenen Dosierungen mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha auf die grünen Pflanzenteile gesprüht. Nach ca. 3 bis 4 Wochen Standzeit der Versuchspflanzen im Gewächshaus unter optimalen Wachstumsbedingungen wird die Wirkung der Präparate optisch im Vergleich zu unbehandelten Kontrollen bonitiert. Die erfindungsgemäßen Mittel weisen auch im Nachauflauf eine gute herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger Ungräser und Unkräuter auf, beispielsweise gegen Schadpflanzen wie Sinapis alba, Echinochloa crus-galli, Lolium multiflorum, Stellaria media, Cyperus iria, Amaranthus retroflexus, Setaria viridis und Avena sativa von den erfindungsgemäßen Verbindungen (siehe Beispiele A1 bis A3 und Verbindungen 2-1 , 2-35, 2-36, 2-45, 2-55, 2-56, 3-1 , 3-14, 3-25, 3-37, 3-38, 3-40, 3-41 , 3-43, 3-44, 3-46, 3-47, 3-55, 3-56, 3-58, 3-59, 3-67, 3-68, 3-70, 3-71 , 3-74, 3-85, 3-86, 3-124, 5-1 , 5-40, 8-2, 8-11, 8-20, 8-21 , 8-27 und 8-37 aus Tabellen 1 bis 12) im Nachauflaufverfahren bei einer Aufwandmenge von 1 kg und weniger Aktivsubstanz pro Hektar.Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds are placed in sandy loam soil in plastic pots, covered with soil and grown in the greenhouse under good growth conditions. Three weeks after sowing, the test plants are treated at the three-leaf stage. The compounds according to the invention formulated as wettable powder or as emulsion concentrates are sprayed onto the green parts of the plant in various dosages with a water application rate of the equivalent of 600 to 800 l / ha. After the test plants have stood in the greenhouse for about 3 to 4 weeks under optimal growth conditions, the effect of the preparations is assessed visually in comparison with untreated controls. The agents according to the invention also have good herbicidal activity against a broad spectrum of economically important grasses and weeds, for example against harmful plants such as Sinapis alba, Echinochloa crus-galli, Lolium multiflorum, Stellaria media, Cyperus iria, Amaranthus retroflexus, Setaria viridis and Avena sativa of the compounds according to the invention (see examples A1 to A3 and compounds 2-1, 2-35, 2-36, 2-45, 2-55, 2-56, 3-1, 3-14, 3-25, 3 -37, 3-38, 3-40, 3-41, 3-43, 3-44, 3-46, 3-47, 3-55, 3-56, 3-58, 3-59, 3-67 , 3-68, 3-70, 3-71, 3-74, 3-85, 3-86, 3-124, 5-1, 5-40, 8-2, 8-11, 8-20, 8 -21, 8-27 and 8-37 from Tables 1 to 12) in the post-emergence process with an application rate of 1 kg and less active substance per hectare.
3. Wirkung auf Schadpflanzen in Reis3. Effect on harmful plants in rice
Verpflanzter und gesäter Reis sowie typische Reisunkräuter und -ungräser werden im Gewächshaus bis zum Dreiblattstadium (Echinochloa crus- galli 1 ,5-Blatt) unter Paddyreis-Bedingungen (Anstauhöhe des Wassers: 2 - 3 cm) in geschlossenen Plastiktöpfen angezogen. Danach erfolgt die Behandlung mit den erfindungsgemäßen Verbindungen. Hierzu werden die formulierten Wirkstoffe in Wasser suspendiert, gelöst bzw. emulgiert und mittels Gießapplikation in das Anstauwasser der Test-pflanzen in unterschiedlichen Dosierungen ausgebracht. Nach der so durchgeführten Behandlung werden die Versuchspflanzen im Gewächshaus unter optimalen Wachstumsbedingungen aufgestellt und während der gesamten Versuchszeit so gehalten.Transplanted and sown rice as well as typical rice weeds and grass weeds are grown in the greenhouse up to the three-leaf stage (Echinochloa crus-galli 1,5-leaf) Paddy rice conditions (water accumulation height: 2 - 3 cm) grown in closed plastic pots. The treatment with the compounds according to the invention is then carried out. For this purpose, the formulated active ingredients are suspended in water, dissolved or emulsified and applied by pouring application into the backwater of the test plants in different dosages. After the treatment has been carried out in this way, the test plants are placed in the greenhouse under optimal growth conditions and are kept this way throughout the test period.
Etwa drei Wochen nach der Applikation erfolgt die Auswertung mittels optischer Bonitur der Pflanzenschäden im Vergleich zu unbehandelten Kontrollen. Die erfindungsgemäßen Verbindungen (siehe Beispiele A1 bis A3 und Verbindungen 2-1 , 2-35, 2-36, 2-45, 2-55, 2-56, 3-1 , 3-14, 3-25, 3-37, 3-38, 3-40, 3-41 , 3-43, 3-44, 3-46, 3-47, 3-55, 3-56, 3-58, 3-59, 3-67, 3-68, 3-70, 3-71 , 3-74, 3-85, 3-86, 3-124, 5-1, 5-40, 8-2, 8-11 , 8-20, 8-21 , 8-27 und 8-37 aus Tabellen 1 bis 12) zeigen sehr gute herbizide Wirkung gegen Schadpflanzen auf, wie z.B. Cyperus monti, Echinochloa crus-galli und Sagittaria pygmaea.About three weeks after application, the evaluation of the plant damage is carried out visually in comparison to untreated controls. The compounds according to the invention (see examples A1 to A3 and compounds 2-1, 2-35, 2-36, 2-45, 2-55, 2-56, 3-1, 3-14, 3-25, 3-37 , 3-38, 3-40, 3-41, 3-43, 3-44, 3-46, 3-47, 3-55, 3-56, 3-58, 3-59, 3-67, 3 -68, 3-70, 3-71, 3-74, 3-85, 3-86, 3-124, 5-1, 5-40, 8-2, 8-11, 8-20, 8-21 , 8-27 and 8-37 from Tables 1 to 12) show very good herbicidal activity against harmful plants, such as Cyperus monti, Echinochloa crus-galli and Sagittaria pygmaea.
4. Kulturpflanzenverträglichkeit4. Compatibility with crops
In weiteren Versuchen im Gewächshaus werden Samen einer größeren Anzahl von Kulturpflanzen und Unkräutern in sandigem Lehmboden ausgelegt und mit Erde abgedeckt. Ein Teil der Töpfe wird sofort wie unter Abschnitt 1 beschrieben behandelt, die übrigen im Gewächshaus aufgestellt, bis die Pflanzen zwei bis drei echte Blätter entwickelt haben und dann wie unter Abschnitt 2 beschrieben mit den erfindungsgemäßen Substanzen der Formel (I) in unterschiedlichen Dosierungen besprüht. Vier bis fünf Wochen nach der Applikation und Standzeit im Gewächshaus wird mittels optischer Bonitur festgestellt, daß die erfindungsgemäßen Verbindungen zweikeimblättrige Kulturen wie z.B. Soja, Baumwolle, Raps, Zuckerrüben und Kartoffeln im Vor- und Nachauflaufverfahren selbst bei hohen Wirkstoffdosierungen ungeschädigt lassen. Einige Substanzen schonen darüber hinaus auch Gramineen- Kulturen wie z.B. Gerste, Weizen, Roggen, Sorghum, Mais oder Reis. Die Verbindungen der Formel (I) zeigen teilweise eine hohe Selektivität und eignen sich deshalb zur Bekämpfung von unerwünschten Pflanzenwuchs in landwirtschaftlichen Kulturen. In further experiments in the greenhouse, seeds of a larger number of crop plants and weeds are planted in sandy loam soil and covered with soil. Some of the pots are treated immediately as described in Section 1, the rest are placed in the greenhouse until the plants have developed two to three true leaves and then sprayed as described in Section 2 with the substances of the formula (I) according to the invention in different dosages. Four to five weeks after application and standing time in the greenhouse, it is determined by means of an optical evaluation that the compounds according to the invention leave dicotyledon crops such as, for example, soybean, cotton, oilseed rape, sugar beet and potatoes pre-and post-emergence, even with high active ingredient doses, undamaged. Some substances also protect Gramineae crops such as barley, wheat, rye, sorghum, corn or rice. The Compounds of the formula (I) show a high selectivity in some cases and are therefore suitable for combating undesired plant growth in agricultural crops.

Claims

Patentansprüche claims
1. Verbindungen der Formel (I) oder deren Salze,1. Compounds of the formula (I) or their salts,
worin wherein
R1 Aryl, Aryloxy, Arylthio, Arylamino, N-Aryl-N-(Cι-C )alkyl-amino, (C3- C9)Cycloalkyl, (C3-C9)Cycloalkyloxy, (C3-C9)Cycloalkylthio, (C3- C9)Cycloalkylamino, N-(C3-Cg)Cycloalkyi-N-(Cι-C4)alkyl-amino, Di-[(C3- Cg)Cycloalkyl]-amino, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio, Heterocyciylamino oder N-Heterocyclyl-N-(d-C4)alkyl-amino, wobei jeder der letztgenannten 16 Reste unsubstituiert oder substituiert ist, oderR 1 aryl, aryloxy, arylthio, arylamino, N-aryl-N- (Cι-C) alkyl-amino, (C 3 - C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyloxy, (C 3 -C 9 ) Cycloalkylthio, (C 3 - C 9 ) cycloalkylamino, N- (C 3 -Cg) cycloalkyi-N- (Cι-C 4 ) alkylamino, di - [(C 3 - Cg) cycloalkyl] amino, heterocyclyl, heterocyclyloxy , Heterocyclylthio, heterocyciylamino or N-heterocyclyl-N- (dC 4 ) alkylamino, each of the latter 16 radicals being unsubstituted or substituted, or
Wasserstoff, (Cι-C6)Alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C6)Alkoxy, (C2- C6)Alkenyloxy, (C2-C6)Alkinyloxy, (Cι-C6)Alkylthio, (C2-C6)AlkenyIthio, (C2- C6)Alkinylthio, (d-C6)Alkyl-amino oder Di-[(d-C6)Alkyl]-amino, wobei jeder der letztgenannten 11 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (Cι-C4)Alkoxy, (Cι-C4)Haloalkoxy, (C2- C4)Alkenyloxy, (C2-C )Haloalkenyloxy, (d-C4)Alkylthio, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (C C4)Haloalkylthio, (d- C4)Haloalkylsulfinyl, (d-C4)Haloalkylsulfonyl, (C3-Cg)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, und Reste der Formeln R,-C(=Z')-, R'-C(=Z,)-Z-, R'-Z-C(=Z,)-) R,R"N-C(=Z')-, R'-Z-C(=Z,)-O-, R'R"N-C(=Z,)-Z-, R'-Z-C(=Z')-NR"- und R,R,,N-C(=Z,)-NR,"-I worin R', R" und R"1 jeweils unabhängig voneinander Wasserstoff, (d-C6)Alkyl, Aryl, Aryl-(d-C6)alkyl, (C3-C9) Cycloalkyl oder (C3- Cg)Cycloalkyl-(Cι-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten und worin Z und Z1 unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist, R2 (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist, (C -Cg)Cycloalkenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, oder Phenyl, das unsubstituiert oder substituiert ist,Hydrogen, (-CC 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 6 ) alkoxy, (C 2 - C 6 ) alkenyloxy, (C 2 - C 6) alkynyloxy, (Cι-C6) alkylthio, (C 2 -C 6) AlkenyIthio, (C 2 - C 6) alkynylthio, (dC 6) alkyl-amino or di - [(dC 6) alkyl] amino , each of the latter 11 residues unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, nitro, thiocyanato, (Cι-C 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (C 2 - C 4 ) Alkenyloxy, (C 2 -C) haloalkenyloxy, (dC 4 ) alkylthio, (d- C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (CC 4 ) haloalkylthio, (d- C 4 ) haloalkylsulfinyl, (dC 4 ) haloalkylsulfonyl, (C 3 -Cg) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, heterocyclyl which is unsubstituted or substituted, and radicals of the formulas R , -C (= Z ') -, R'-C ( = Z , ) -Z-, R'-ZC (= Z , ) - ) R , R "NC (= Z ') -, R'-ZC (= Z , ) -O-, R'R" NC ( = Z , ) -Z-, R'-ZC (= Z ') - NR "- and R , R ,, NC (= Z , ) -NR , " - I wherein R ', R "and R" 1 are each independently hydrogen, (dC 6 ) alkyl, aryl, aryl- (dC 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 - Cg) cycloalkyl- (Cι -C 6 ) alkyl, where each of the last 5 radicals is unsubstituted or substituted, and in which Z and Z 1 are each independently an oxygen or sulfur atom, R 2 (C 3 -C 9 ) cycloalkyl which is unsubstituted or is substituted, (C -Cg) cycloalkenyl which is unsubstituted or substituted, heterocyclyl which is unsubstituted or substituted, or phenyl which is unsubstituted or substituted,
R3 eine Gruppe — U-* R 3 a group - U- *
worinwherein
L1 eine direkte Bindung, -O-, -S- oder eine Gruppe der Formel -NG2-,L 1 is a direct bond, -O-, -S- or a group of the formula -NG 2 -,
U1, U2 unabhängig voneinander eine Gruppe der Formel G3, OG4, SG5,U 1 , U 2 independently of one another are a group of the formula G 3 , OG 4 , SG 5 ,
NG6G7, NG8NG9G10, NG11OG12 oder NG11SG12,NG 6 G 7 , NG 8 NG 9 G 10 , NG 11 OG 12 or NG 11 SG 12 ,
U3 eine Gruppe der Formel G13, OG14, SG15, NG16G17, NG18NG19G20,U 3 is a group of the formula G 13 , OG 14 , SG 15 , NG 16 G 17 , NG 18 NG 19 G 20 ,
NG21OG22 oder NG23SG24,NG 21 OG 22 or NG 23 SG 24 ,
U4 eine Gruppe der Formel G25, OG26, SG27 oder NG28G29 bedeuten, wobei die Reste G1 bis G29 unabhängig voneinanderU 4 is a group of the formula G 25 , OG 26 , SG 27 or NG 28 G 29 , the radicals G 1 to G 29 being independent of one another
Wasserstoff, Aryl, das unsubstituiert oder substituiert ist, oderHydrogen, aryl, which is unsubstituted or substituted, or
(C3-Cg)Cycloalkyl, das unsubstituiert oder substituiert ist, oder Heterocyclyl, das substituiert oder unsubstituiert ist, oder(C 3 -Cg) cycloalkyl which is unsubstituted or substituted, or heterocyclyl which is substituted or unsubstituted, or
(d-C6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl bedeuten, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (Cι-C )Alkoxy, (Cι-C4) Haloalkoxy, (C2-C4)Alkenyioxy, (C2-C4)Haloalkenyloxy, (d-C4)Alkylthio, (d-C4)Alkylsulfinyl, (C C4)Alkylsulfonyl, (Cι-C4)Haloalkylsulfinyl, (d-C4)Haloalkylsulfonyl, (C3-Cg)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, und Reste der Formeln R'-C(=Z')-, R,-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N-C(=Z')-, R'-Z-C(=Z,)-O-) R'R"N-C(=Z,)-Z-, R,-Z-C(=Z')-NR"- und R'R"N-C(=Z,)-NR'"-, worin R\ R" und R'" jeweils unabhängig voneinander Wasserstoff, (d- C6)Alkyl, Aryl, Aryl-(C-,-C6)alkyl, (C3-C9)Cycloalkyl oder (C3- Cg)Cycloalkyl-(Cι-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist und inklusive Substituenten vorzugsweise 1 bis 30 C-Atome aufweist, oder die Reste U1 und U3 oder U2 und U4 oder U2 und G1 oder U4 und G1 paarweise mit den sie verbindenden Atomen jeweils einen carbocyclischen bzw. heterocyclischen Ring mit 4 bis 7 Ringatomen bedeuten, wobei der Ring unsubstituiert oder substituiert ist, R4 einen Rest der Formel -B1-D1, wobei B1 und D1 wie unten definiert sind, A1 eine direkte Bindung oder geradkettiges Alkylen mit 1 bis 5 C-Atomen oder geradkettiges Alkenylen oder Alkinylen mit jeweils 2 bis 5 C-Atomen, wobei jeder der drei letztgenannten Diradikale unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Cyano, Thiocyanato und Reste der Formel -B2-D2 substituiert ist, wobei B2 und D2 wie unten definiert sind, A2 eine direkte Bindung oder geradkettiges Alkylen mit 1 bis 4 C-Atomen oder geradkettiges Alkenylen oder Alkinylen mit jeweils 2 bis 5 C-Atomen, wobei jeder der drei letztgenannten Diradikale unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Cyano, Thiocyanato und Reste der Formel -B3-D3 substituiert ist, oder ein divalenter Rest der Formel V1, V2, V3, V4 oderV5, -CRaRb-W*-CRcRd- (V1) -CRaRb-W*-CRcRd-CReRf- (V2)(dC 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, nitro, thiocyanato , (-C-C) alkoxy, (-C-C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyioxy, (C 2 -C 4 ) Haloalkenyloxy, (dC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (CC 4 ) alkylsulfonyl, (Cι-C 4 ) haloalkylsulfinyl, (dC 4 ) haloalkylsulfonyl, (C 3 -Cg) cycloalkyl, that is unsubstituted or substituted, phenyl which is unsubstituted or substituted, heterocyclyl which is unsubstituted or substituted, and radicals of the formulas R'-C (= Z ') -, R , -C (= Z') - Z-, R '-ZC (= Z') -, R'R "NC (= Z ') -, R'-ZC (= Z , ) -O- ) R'R" NC (= Z , ) -Z-, R , -ZC (= Z ') - NR "- and R'R" NC (= Z , ) -NR'"-, wherein R \ R" and R '"each independently of one another hydrogen, (d-C 6 ) alkyl , Aryl, aryl- (C -, - C 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 - Cg) cycloalkyl- (Cι-C 6 ) alkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted , mean and in which Z and Z 'are each independently an oxygen or sulfur atom, is substituted and preferably has 1 to 30 carbon atoms, including substituents, or the radicals U 1 and U 3 or U 2 and U 4 or U 2 and G 1 or U 4 and G 1 in pairs with the they connecting atoms each represent a carbocyclic or heterocyclic ring having 4 to 7 ring atoms, the ring being unsubstituted or substituted, R 4 being a radical of the formula -B 1 -D 1 , where B 1 and D 1 are as defined below, A 1 is a direct bond or straight-chain alkylene with 1 to 5 C atoms or straight-chain alkenylene or alkynylene each with 2 to 5 C atoms, each of the three last-mentioned diradicals being unsubstituted or by one or more radicals from the group halogen, nitro, cyano, Thiocyanato and radicals of the formula -B 2 -D 2 is substituted, wherein B 2 and D 2 are as defined below, A 2 is a direct bond or straight-chain alkylene having 1 to 4 carbon atoms or straight-chain alkenylene or alkynylene each having 2 to 5 C atoms, where each of the last three diradicals is unsubstituted or substituted by one or more radicals from the group halogen, nitro, cyano, thiocyanato and radicals of the formula -B 3 -D 3 , or a divalent r radical of the formula V 1 , V 2 , V 3 , V 4 or V 5 , -CR a R b -W * -CR c R d - (V 1 ) -CR a R b -W * -CR c R d -CR e R f - (V 2 )
-CRaRb-CRcRd-W*-CReRf- (V3)-CR a R b -CR c R d -W * -CR e R f - (V 3 )
-CRaRb-CRcRd-W*- (V4)-CR a R b -CR c R d -W * - (V 4 )
-CRaRb-W*- (V5) wobei jeder der Reste Ra, Rb, Rc, Rd, Re und Rf jeweils unabhängig voneinander Wasserstoff, Halogen, Nitro, Cyano, Thiocyanato oder ein Rest der Formel -B4-D4 ist,-CR a R b -W * - (V 5 ) where each of the radicals R a , R b , R c , R d , R e and R f each independently of one another hydrogen, halogen, nitro, cyano, thiocyanato or a radical of Formula -B 4 -D 4 is
W* jeweils ein Sauerstoffatom, ein Schwefelatom oder eine Gruppe derW * each represents an oxygen atom, a sulfur atom or a group of
Formel N(B5-D5) ist undFormula N (B 5 -D 5 ) is and
B3, B4, B5, D3, D4 und D5 wie unten definiert sind,B 3 , B 4 , B 5 , D 3 , D 4 and D 5 are as defined below,
B1 und B5 jeweils unabhängig voneinander eine direkte Bindung oder eine divalente Gruppe der Formeln -C(=Z*)-, -C(=Z*)-Z**-, -C(=Z*)-NH- oder -C(=Z*)-NR*-, wobei Z* = ein Sauerstoff- oder Schwefelatom, Z** = ein Sauerstoff- oder Schwefelatom und R* = (d-C6)Alkyl, Aryl, Aryl-(d-C6)alkyl, (C3-C9)Cycloalkyl oder (C3-C9)Cycloalkyl-(Cι-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist,B 1 and B 5 each independently of one another are a direct bond or a divalent group of the formulas -C (= Z *) -, -C (= Z *) - Z ** -, -C (= Z *) - NH- or -C (= Z *) - NR * -, where Z * = an oxygen or sulfur atom, Z ** = an oxygen or sulfur atom and R * = (dC 6 ) alkyl, aryl, aryl (dC 6 ) alkyl , (C 3 -C 9 ) cycloalkyl or (C 3 -C 9 ) cycloalkyl- (Cι-C 6 ) alkyl, each of the 5 latter radicals being unsubstituted or substituted,
B2, B3 und B4 jeweils unabhängig voneinander eine direkte Bindung oder eine divalente Gruppe der Formeln -O-, -S(O)p-, -S(O)p-O-, -O-S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR° -, -O-NR0-, -NR°-O-, -NR°-CO-, -CO-NR0-, -O-CO-NR0- oder -NR°-CO-O-, wobei p die ganze Zahl 0, 1 oder 2 ist und R° Wasserstoff, (Cι-C6)Alkyl, Aryl, Aryl-(d-C6)alkyl, (C3-C9)Cycloalkyl oder (C3-C9)Cycloalkyl-(C -C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeutet,B 2 , B 3 and B 4 each independently of one another are a direct bond or a divalent group of the formulas -O-, -S (O) p -, -S (O) p -O-, -OS (O) p -, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR ° -, -O-NR 0 -, -NR ° -O-, -NR ° -CO-, -CO-NR 0 -, -O-CO-NR 0 - or -NR ° -CO-O-, where p is the integer 0, 1 or 2 and R ° is hydrogen, (-CC 6 ) alkyl, aryl, aryl- (dC 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 -C 9 ) cycloalkyl - (C -C 6 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted,
D1, D2, D3, D4 und D5 jeweils unabhängig voneinander Wasserstoff, (d-C6JAIkyl, Aryl, Aryl-(Cι-C6)alkyl, (C3-C9)Cycloalkyl oder (C3-Cg)Cycloalkyl-(d-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, oder jeweils zwei Reste D3 von an einem C-Atom gebundenen zwei Gruppen -B3-D3 miteinander verbunden sind und eine Alkylengruppe mit 2 bis 4 C- Atomen ergeben, die unsubstituiert oder durch einen oder mehrere Reste aus . der Gruppe (d-C4)Alkyl und (d-C )Alkoxy substituiert ist,D 1 , D 2 , D 3 , D 4 and D 5 each independently of one another hydrogen, (dC 6 JAIkyl, aryl, aryl- (-C-C 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 -Cg ) Cycloalkyl- (dC 6 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, or in each case two radicals D 3 of two groups -B 3 -D 3 bonded to a carbon atom are connected to one another and an alkylene group with 2 to 4 carbon atoms which are unsubstituted or substituted by one or more radicals from the group (dC 4 ) alkyl and (dC) alkoxy,
L° eine direkte Bindung, Sauerstoff, Schwefel oder eine Gruppe NG30, worin der Rest G30 Wasserstoff, Aryl, das unsubstituiert oder substituiert ist, oder (C3-Cg)Cycloalkyl, das unsubstituiert oder substituiert ist, oder Heterocyclyl, das substituiert oder unsubstituiert ist, oder (d-C6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (CrC4)Alkoxy, (d-C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C )Haloalkenyloxy, (C C4)Alkylthio, (Cι-C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (Cι-C4)Haloalkylsulfinyl, (d-C4)Haloalkylsulfonyl, (C3-C9)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, und Reste der Formeln R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-, R-R-N-C^Z')-, R'-Z-C(=Z,)-O-, R'R"N-C(=Z,)-Z-, R'-Z-C(=Z')-NR"- und R'R"N-C(=Z,)-NR",-I worin R', R" und R'" jeweils unabhängig voneinander Wasserstoff, (d- C6)Alkyl, Aryl, Aryl-(d-C6)alkyl, (C3-C9)Cycloalkyl oder (C3-C9)- Cycloalkyl-(Cι-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist, (X)n n Substituenten X und dabei X jeweils unabhängig voneinander Halogen,L ° is a direct bond, oxygen, sulfur or a group NG 30 , in which the rest G 30 Hydrogen, aryl which is unsubstituted or substituted, or (C 3 -Cg) cycloalkyl which is unsubstituted or substituted, or heterocyclyl which is substituted or unsubstituted, or (dC 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, nitro, thiocyanato, (CrC 4 ) alkoxy, (dC 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C) haloalkenyloxy, (CC 4 ) alkylthio, (Cι-C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (Cι-C 4 ) haloalkylsulfinyl, (dC 4 ) haloalkylsulfonyl, (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, heterocyclyl which is unsubstituted or substituted, and radicals of the formulas R'-C (= Z ') -, R'-C (= Z ') - Z-, R'-ZC (= Z') -, RRNC ^ Z ') -, R'-ZC (= Z , ) -O-, R'R "NC (= Z , ) -Z -, R'-ZC (= Z ') - NR "- and R'R" NC (= Z , ) -NR " , - I where R', R" and R '"are each independently hydrogen, (d- C 6 ) alkyl, aryl, aryl- (dC 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 -C 9 ) - cycloalkyl- (Cι-C 6 ) alkyl, each of the 5 latter radicals being unsubstituted or substituted is and where Z and Z 'are each independently an oxygen or sulfur atom, substituted, (X) n n substituents X and X in each case independently of one another halogen,
Hydroxy, Amino, Nitro, Formyl, Carboxy, Cyano, Thiocyanato, Aminocarbonyl oder (Cι-C6)Alkyl, (Cι-C6)Alkoxy, (Cι-C6)Alkylthio, Mono(d-C6)alkylamino, Di(Cι-C4)alkylamino, (C2-C6)Alkenyl, (C2-C6)Alkinyl, [(CrC6)Alkoxy]carbonyl, Mono(d-C6)alkylamino-carbonyl Di(d-C )alkylamino-carbonyl, N-(C C6)Alkanoyl-amino oder N-(CrC )Alkanoyl-N-(Cι-C4)alkyl-amino, wobei jeder der letztgenannten 13 Reste unsubstituiert oder substituiert ist, oder (C3-C8)Cycloalkyl, (C3-C8)Cycloalkoxy, (C3-Cg)Cycloalkylamino, Phenyl, Phenoxy, Phenylthio, Phenylcarbonyl, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio oder Heterocyciylamino, wobei jeder der letztgenannten 11 Reste unsubstituiert oder substituiert ist, oder zwei benachbarte Reste X gemeinsam einen ankondensierten Cyclus mit 4 bis 6 Ringatomen, der carbocyclisch ist oder Heteroringatome aus der Gruppe O, S und N enthält und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (d-C )Alkyl und Oxo substituiert ist, n 0, 1 , 3, 4 oder 5 undHydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, aminocarbonyl or (Cι-C 6 ) alkyl, (Cι-C 6 ) alkoxy, (Cι-C 6 ) alkylthio, mono (dC 6 ) alkylamino, di (Cι -C 4 ) alkylamino, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, [(CrC 6 ) alkoxy] carbonyl, mono (dC 6 ) alkylamino-carbonyl di (dC) alkylamino-carbonyl, N- (CC 6 ) alkanoyl-amino or N- (CrC) alkanoyl-N- (Cι-C 4 ) alkylamino, where each of the latter 13 radicals is unsubstituted or substituted, or (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkoxy, (C 3 -Cg) cycloalkylamino, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyciylamino, each of the latter 11 residues being unsubstituted or is substituted, or two adjacent radicals X together form a fused-on cycle with 4 to 6 ring atoms, which is carbocyclic or contains hetero ring atoms from the group O, S and N and which is unsubstituted or by one or more radicals from the group halogen, (dC) Alkyl and oxo is substituted, n is 0, 1, 3, 4 or 5 and
Heterocyclyl in den vorstehend genannten Resten unabhängig voneinander jeweils einen heterocyclischen Rest mit 3 bis 7 Ringatomen und 1 bis 3 Heteroatomen aus der Gruppe N, O und S bedeuten.Heterocyclyl in the radicals mentioned above each independently represent a heterocyclic radical with 3 to 7 ring atoms and 1 to 3 heteroatoms from the group N, O and S.
2. Verbindungen und deren Salze nach Anspruch 1 , dadurch gekennzeichnet, dass2. Compounds and their salts according to claim 1, characterized in that
R1 Phenyl, Phenoxy, Phenylthio, Phenylamino, N-Phenyl-N-(Cι-C )alkyl-amino, wobei jeder der letztgenannten 5 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (Cι-C4)Alkyl, (Cι-C4)Haloalkyl, (d-C4)Alkoxy, (d-C )Haloalkoxy, (C C4)Alkylthio, (d-C4)Haloalkylthio, Mono(Cι-C )alkylamino, Di(Cι-C4)alkylamino, (C3-Cg)Cycloalkyl, [(Cι-C )Alkyl]carbonyl, [(d-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(Cι-C4)alkylamino-carbonyl, (CrC )Alkylsulfonyl und (CrC )Haloalkylsulfonyl substituiert ist und inklusive Substituenten 6 bis 30 C-Atome aufweist, oderR 1 phenyl, phenoxy, phenylthio, phenylamino, N-phenyl-N- (-C-C) alkyl-amino, where each of the latter 5 residues unsubstituted or by one or more residues from the group halogen, hydroxy, amino, nitro, formyl , Carboxy, sulfo, cyano, thiocyanato, (Cι-C 4 ) alkyl, (Cι-C 4 ) haloalkyl, (dC 4 ) alkoxy, (dC) haloalkoxy, (CC 4 ) alkylthio, (dC 4 ) haloalkylthio, mono ( -C-C) alkylamino, di (-C-C 4 ) alkylamino, (C 3 -Cg) cycloalkyl, [(Cι-C) alkyl] carbonyl, [(dC 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino-carbonyl, di (Cι-C 4 ) alkylamino-carbonyl, (CrC) alkylsulfonyl and (CrC) haloalkylsulfonyl is substituted and has 6 to 30 C atoms including substituents, or
(C3-Cg)Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Thiocyanato, (C C )Alkyl, (Ct-C4)Haloalkyl, (C C4)Alkoxy, (d-C4)Haloalkoxy, (C C4)Alkylthio, (d-C4)Haloalkylthio, Mono(C C4)alkylamino und Di(d-C4)alkylamino substituiert ist und inklusive Substituenten 3 bis 30 C-Atome aufweist, oder(C 3 -Cg) cycloalkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (CC) alkyl, (C t -C 4 ) haloalkyl, (CC 4 ) alkoxy, ( dC 4 ) haloalkoxy, (CC 4 ) alkylthio, (dC 4 ) haloalkylthio, mono (CC 4 ) alkylamino and di (dC 4 ) alkylamino is substituted and has 3 to 30 C atoms including substituents, or
Heterocyclyl, das unsubstituiert oder durch einen oder mehrere Reste aus derHeterocyclyl, which is unsubstituted or by one or more residues from the
Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano,Group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano,
Thiocyanato, (d-C4)Alkyl, (Cι-C4)Haloalkyl, (C C4)Alkoxy,Thiocyanato, (dC 4 ) alkyl, (Cι-C 4 ) haloalkyl, (CC 4 ) alkoxy,
(d-C4)Haloalkoxy, (d-C4)Alkylthio, (Cι-C4)Haloalkylthio,(dC 4 ) haloalkoxy, (dC 4 ) alkylthio, (-C-C 4 ) haloalkylthio,
Mono(Cι-C4)aIkyiamino, Di(d-C )alkylamino, (C3-Cg)Cycloalkyl,Mono (-C-C 4 ) aIkyiamino, di (dC) alkylamino, (C 3 -Cg) cycloalkyl,
[(Cι-C4)Alkyl]carbonyl, [(CrC )Alkoxy]carbonyl, Aminocarbonyl,[(-CC 4 ) alkyl] carbonyl, [(CrC) alkoxy] carbonyl, aminocarbonyl,
Mono(Cι-C4)alkylamino-carbonyl, Di(Cι-C4)alkylamino-carbonyl,Mono (-C-C 4 ) alkylamino-carbonyl, di (Cι-C 4 ) alkylamino-carbonyl,
(Cι-C4)Alkylsulfonyl und (Cι-C4)Haloalkylsulfonyl substituiert ist und inklusive(-C-C 4 ) alkylsulfonyl and (-C-C 4 ) haloalkylsulfonyl is substituted and inclusive
Substituenten 2 bis 30 C-Atome aufweist, oderHas substituents 2 to 30 carbon atoms, or
Wasserstoff oder (d-CβJAlkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (d-C6)Alkoxy oder (d-C6)Alkylthio, wobei jeder der letztgenannten 5 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato,Hydrogen or (d-CβJalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (dC 6 ) alkoxy or (dC 6 ) alkylthio, each of the latter 5 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, nitro, thiocyanato,
(Cι-C4)Alkoxy, (d-C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C )Haloalkenyloxy,(-C-C 4 ) alkoxy, (dC 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C) haloalkenyloxy,
(Cι-C4)Alkylthio, (d-C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-(-C-C 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (d-
C4)Haloalkylsulfinyl, (Cι-C4)Haloalkylsulfonyl undC 4 ) haloalkylsulfinyl, (-C-C 4 ) haloalkylsulfonyl and
(C3-C6)Cycloalkyl, das unsubstituiert oder oder durch einen oder mehrere(C 3 -C 6 ) Cycloalkyl which is unsubstituted or or by one or more
Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Thiocyanato, (C C )Alkyl, (d-C4)Haloalkyl, (Cι-C4)Alkoxy, (C C4)Haloalkoxy, (Cι-C4)Alkylthio, (C1-C4)Haloalkylthio, Mono(Cι-C4)alkylamino und Di(Cι-C4)alkylamino substituiert ist, und Phenyl und Heterocyclyl, wobei jeder der zwei letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (d-C4)Alkyl, (Cι-C4)Haloalkyl, (C1-C )Alkoxy, (d-C4)Haloalkoxy, (C C4)Alkylthio, (d-C4)Haloalkylthio, Mono(Cι-C4)alkylamino, Di(CrC4)alkylamino, (C3-C9)Cycloalkyl, [(Cι-C4)Alkyl]carbonyl, [(d-C )Alkoxy]carbonyl, Aminocarbonyl, Mono(d-C4)alkylamino-carbonyl, Di(Cι-C )alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl und (Cι-C4)Haloalkylsulfonyl substituiert ist, und Reste der Formeln R,-C(=Z')-> R'-C(=Z')-Z-, R'-Z-C(=Z,)-) R,R"N-C(=Z')-, R'-Z-C(=Z')-O-, R'R"N-C(=Z,)-Z-, R'-Z-C(=Z')-NR"- und R'R,,N-C(=Z,)-NR",-) worin R\ R" und R'" jeweils unabhängig voneinander Wasserstoff, (C1-C4)Alkyl, Phenyl, Phenyl-(d-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(CrC4)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Cyano, Thiocyanato, (Cι-C4)Alkoxy, (Cι-C )Alkylthio, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl und im Fall cyclischer Reste auch (Cι-C )Alkyl und (d-C4)Haloalkyl substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist, und (C3-C9)Cycloalkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe der Reste A), B), C) und D) substituiert ist, wobei Gruppe A) aus den Resten Halogen, Hydroxy, Amino, Nitro, Formyl,Radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (CC) alkyl, (dC 4 ) haloalkyl, (Cι-C 4 ) alkoxy, (CC 4 ) haloalkoxy, (Cι-C 4 ) alkylthio, (C 1 -C 4 ) Haloalkylthio, mono (-C-C 4 ) alkylamino and di (Cι-C 4 ) alkylamino is substituted, and phenyl and heterocyclyl, each of the latter two radicals unsubstituted or by one or more radicals from the group halogen, hydroxy , Amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (dC 4 ) alkyl, (Cι-C 4 ) haloalkyl, (C 1 -C) alkoxy, (dC 4 ) haloalkoxy, (CC 4 ) alkylthio, ( dC 4 ) haloalkylthio, mono (-C-C 4 ) alkylamino, di (CrC 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(Cι-C 4 ) alkyl] carbonyl, [(dC) alkoxy] carbonyl, aminocarbonyl . Mono (dC 4 ) alkylamino-carbonyl, di (Cι-C) alkylamino-carbonyl, (Cι-C 4 ) alkylsulfonyl and (Cι-C 4 ) haloalkylsulfonyl is substituted, and residues of the formulas R , -C (= Z ') - > R'-C (= Z ') - Z-, R'-ZC (= Z , ) - ) R , R "NC (= Z') -, R'-ZC (= Z ') - O- , R'R "NC (= Z , ) -Z-, R'-ZC (= Z ') - NR" - and R'R ,, NC (= Z , ) -NR " , - ) where R \ R "and R '" each independently of one another hydrogen, (C 1 -C 4 ) alkyl, phenyl, phenyl- (dC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (CrC 4 ) alkyl, each of the 5 last-mentioned radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, cyano, thiocyanato, (-C-C 4 ) alkoxy, (Cι-C) alkylthio, mono ( C 1 -C 4 ) alkylamino, di (C 1 -C 4 ) alkylamino, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl and in the case of cyclic radicals also (Cι -C) alkyl and (dC 4 ) haloalkyl is substituted, and where Z and Z 'are each independently an oxygen or sulfur atom, and ( C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted by one or more radicals from the group consisting of radicals A), B), C) and D), where group A) consists of the radicals halogen, hydroxy, amino, nitro, formyl,
Carboxy, Aminocarbonyl, Sulfo, Cyano, Thiocyanato und Oxo besteht,Carboxy, aminocarbonyl, sulfo, cyano, thiocyanato and oxo,
Gruppe B) aus den Resten (d-C6)Alkyl, (d-C6)Alkoxy, (Cι-C6)Alkylthio, Mono(d-C6)alkylamino, Di(Cι-C4)alkylamino, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C3-C9)Cycloalkyl, (C4-C9)Cycloalkenyl, (C C6)Alkyliden, (C4-Cg)Cycloalkyliden, Resten der Formeln R'-C(=Z,)-> R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N-C(=Z')-, R'-Z-C(=Z')-O-, R'R"N-C(=Z')-Z-, R'-Z-C(=Z')-NR"- und R,R"N-C(=Z,)-NR",-) worin R', R" und R'" jeweils unabhängig voneinander Wasserstoff, (d-C6)Alkyl, Phenyl, Phenyl-(d-C6)alkyl, (C3-C9)Cycloalkyl oder (C3-C9)Cycloalkyl-(Cι-C6)alkyl bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, besteht, Gruppe C) aus Resten gemäß Gruppe B) besteht, wobei jedoch jeder Rest durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (d-C )Alkoxy, (d-C )Haloalkoxy, (CrC )Alkylthio, (d-C4)Haloalkylthio, Mono(Cι-C4)alkylamino, Di(d-C4)alkylamino, (C3-C9)Cycloalkyl, (C -C9)Cycloa!kylen, (C -C9)Cycloalkyliden, [(Cι-C )Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl, Di(CrC4)alkylamino-carbonyl, Phenyl, Phenoxy, Phenylthio, Phenylcarbonyl, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio und Heterocyciylamino, wobei jeder der letztgenannten 21 Reste unsubstituiert ist oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Cyano, (Cι-C4)Alkoxy, (d-C4)Alkylthio, (Cι-C4)Haloalkoxy, Formyl, (Cι-C4)Alkyl-carbonyl und (Cι-C4)Alkoxy-carbonyl und im Falle von cyclischen Resten auch (Cι-C4)Alkyl, (Cι-d)Haloalkyl und (Cι-C6)Alkyliden substituiert ist, und im Falle von cyclischen Resten auch (Cι-C6)Alkyl, (Cι-C6)Haloalkyl und (d-C6)Alkyliden substituiert ist, und Gruppe D) aus divalenten oder trivalenten aliphatischen Brücken mit 1 bis 6, vorzugsweise 1 bis 4 C-Atomen, besteht, die im Fall von divalenten Brücken zwei bzw. im Fall von trivalenten Brücken drei C-Atome des cyclischen Grundkörpers verbinden und der Rest R2 dadurch der Rest eines Bicyclus bzw. Tricyclus darstellt, wobei jeder der Brücken unsubstituiert oder durch einen oder mehrere Substituenten aus der Gruppe Halogen, Nitro, Cyano, (Cι-C4)Alkyl, (Cι-C4)Alkoxy, (d-C4)Alkylthio, (d-C4)Haloalkyl, (Cι-C4)Haloalkoxy, Formyl, (d-C )Alkyl-carbonyl, (Cι-C )Alkoxy-carbonyl und Oxo substituiert ist, und wobei R2 inklusive Substituenten 3 bis 20 C-Atome aufweist, oder R2 (C -C9)CycIoalkenyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe der Reste A), B), C) und D) substituiert ist, wie sie als Reste für den Fall R2 = (C3-C9)Cycloalkyl definiert sind, und dabei inklusive Substituenten 4 bis 20 C-Atome aufweist, oderGroup B) from the residues (dC 6 ) alkyl, (dC 6 ) alkoxy, (Cι-C 6 ) alkylthio, mono (dC 6 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 2 -C 6 ) alkenyl , (C 2 -C 6 ) alkynyl, (C 3 -C 9 ) cycloalkyl, (C 4 -C 9 ) cycloalkenyl, (CC 6 ) alkylidene, (C 4 -Cg) cycloalkylidene, residues of the formulas R'-C ( = Z , ) - > R'-C (= Z ') - Z-, R'-ZC (= Z') -, R'R "NC (= Z ') -, R'-ZC (= Z' ) -O-, R'R "NC (= Z ') - Z-, R'-ZC (= Z') - NR" - and R , R "NC (= Z , ) -NR" , - ) where R ', R "and R'" each independently of one another hydrogen, (dC 6 ) alkyl, phenyl, phenyl- (dC 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 -C 9 ) cycloalkyl- (Cι Are -C 6 ) alkyl and where Z and Z 'are each independently an oxygen or sulfur atom, Group C) consists of radicals according to group B), but each radical consists of one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (dC) alkoxy, (dC) haloalkoxy , (CrC) alkylthio, (dC 4 ) haloalkylthio, mono (Cι-C 4 ) alkylamino, di (dC 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, (C -C 9 ) cycloa! Kylene, (C - C 9 ) cycloalkylidene, [(-C-C) alkyl] carbonyl, [(-C-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C 4 ) alkylamino-carbonyl, di (CrC 4 ) alkylamino-carbonyl, phenyl, Phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyciylamino, where each of the latter 21 radicals is unsubstituted or by one or more radicals from the group halogen, nitro, cyano, (C 1 -C 4 ) alkoxy, (dC 4 ) alkylthio , (-C-C 4 ) haloalkoxy, formyl, (Cι-C 4 ) alkyl-carbonyl and (Cι-C 4 ) alkoxy-carbonyl and in the case of cyclic radicals also (Cι-C 4 ) alkyl, (Cι-d) Haloalkyl and (-C-C 6 ) alkylidene is substituted, and in the case of cyclic radicals also (-CC 6 ) alkyl, (-CC 6 ) haloalkyl and (dC 6 ) alkylidene is substituted, and group D) from divalent or trivalent aliphatic bridges with 1 to 6, preferably 1 to 4 C atoms, which connect two C atoms of the cyclic base body in the case of divalent bridges or three in the case of trivalent bridges, and the radical R 2 thereby represents the radical of a bicyclus or tricyclus, each of the bridges being unsubstituted or by one or more substituents from the group halogen, nitro, cyano, (-C-C 4 ) alkyl, (Cι-C 4 ) alkoxy, (dC 4 ) alkylthio, (dC 4 ) haloalkyl, (Cι-C 4 ) haloalkoxy, formyl , (dC) alkyl-carbonyl, (-CC) alkoxy-carbonyl and oxo is substituted, and wherein R 2 including substituents has 3 to 20 C atoms, or R 2 (C -C 9 ) cycloalkenyl, which is unsubstituted or substituted by one or more radicals from the group consisting of radicals A), B), C) and D), as radicals for the case R 2 = (C 3 -C 9 ) Cycloalkyl are defined, and including 4 to 20 carbon atoms including substituents, or
R2 Heterocyclyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe der Reste A), B), C) und D) substituiert ist, wie sie als Reste für den Fall R2 = (C3-Cg)Cycloalkyl definiert sind, oderR 2 heterocyclyl which is unsubstituted or substituted by one or more radicals from the group consisting of radicals A), B), C) and D), as defined as radicals for the case R 2 = (C 3 -Cg) cycloalkyl , or
R2 Phenyl, das unsubstituiert oder durch einen oder mehrere Reste aus derR 2 phenyl which is unsubstituted or by one or more radicals from the
Gruppe der Reste A), B) und C) substituiert ist, wie sie als Reste für R2 = (C3- C9)Cycloalkyl definiert sind, wobei R2 inklusive Substituenten bis 20 C-Atome aufweist, bedeuten.Group of the radicals A), B) and C) is substituted as they are defined as radicals for R 2 = (C 3 - C 9 ) cycloalkyl, where R 2 including substituents has up to 20 C atoms.
3. Verbindungen und deren Salze nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass R3 einen Rest der Formel3. Compounds and their salts according to claim 1 or 2, characterized in that R 3 is a radical of the formula
R5 R 5
bedeutet, wobeimeans where
R6 und R7 gemeinsam mit dem Stickstoffatom der Gruppe NR6R7,R 6 and R 7 together with the nitrogen atom of group NR 6 R 7 ,
R7 und OR8 gemeinsam mit dem Stickstoffatom der Gruppe NOR8R7,R 7 and OR 8 together with the nitrogen atom of the group NOR 8 R 7 ,
R7 und SR8 gemeinsam mit dem Stickstoffatom der Gruppe NSR8R7,R 7 and SR 8 together with the nitrogen atom of the group NSR 8 R 7 ,
R10 und R11 gemeinsam mit dem Stickstoffatom der Gruppe NR10R11,R 10 and R 11 together with the nitrogen atom of group NR 10 R 11 ,
OR12 und OR13 bzw. SR12 und SR13 gemeinsam mit dem Kohlenstoffatom derOR 12 and OR 13 or SR 12 and SR 13 together with the carbon atom of the
Gruppen der FormelnGroups of formulas
OR und R bzw. SRÖ und R >14 gemeinsam mit dem Kohlenstoffatom der Gruppen R5 OR and R or SR Ö and R> 14 together with the carbon atom of the groups R 5
R14 und R15 gemeinsam mit dem Kohlenstoffatom der Gruppe R5 und R7 gemeinsam mit der AtomgruppierungR 14 and R 15 together with the carbon atom of the group R 5 and R 7 together with the atom grouping
R und R >17 gemeinsam mit dem Kohlenstoffatom der Gruppe R and R> 17 together with the carbon atom of the group
R5 und R16 gemeinsam mit der AtomgruppeR 5 and R 16 together with the atomic group
der Gruppe the group
R7 und R10 gemeinsam mit der AtomgruppierungR 7 and R 10 together with the atom grouping
der Gruppe the group
jeweils unabhängig voneinander einen carbocyclischen bzw. heterocyclischen Ring mit 3 bis 7 Ringatomen und 1 bis 6 Heteroatomen, wobei die gegebenenfalls weiteren Heteroringatome aus der Gruppe N, O und S ausgewählt sind und der carbocyclische oder heterocycl ische Ring jeweils unsubstituiert oder substituiert ist, bilden, und die Reste R5, R6, R7, R8, R9, R10, R11, R14, R15, R16, R17 in den vorstehenden Formeln unabhängig voneinandereach independently of one another a carbocyclic or heterocyclic ring with 3 to 7 ring atoms and 1 to 6 heteroatoms, the further hetero ring atoms optionally being selected from the group N, O and S and the carbocyclic or heterocyclic ring being unsubstituted or substituted, form, and the radicals R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 14 , R 15 , R 16 , R 17 in the above formulas independently of one another
Wasserstoff, Aryl, das unsubstituiert oder substituiert ist, oder (C3-Hydrogen, aryl which is unsubstituted or substituted, or (C 3 -
C9)Cycloalkyl, das unsubstituiert oder substituiert ist, oder Heterocyclyl, das substituiert oder unsubstituiert ist, oderC 9 ) cycloalkyl which is unsubstituted or substituted, or heterocyclyl which is substituted or unsubstituted, or
(d-C6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (CrC4)Alkoxy, (Cι-C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (C1-C4)Alkylthio, (Cι-C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (Cι-C4)Haloalkylsulfinyl, (d-C4)Haloalkylsulfonyl, (C3-Cg)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, und Reste der Formeln R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-, R*R"N-C(=Z')-, R'-Z-C(=Z')-O-, R'R"N-C(=Z,)-Z-, R'-Z-C(=Z,)-NR"- und R^'N-C^-NR'"-, worin R', R" und R'" jeweils unabhängig voneinander Wasserstoff, (d- C6)Alkyl, Aryl, Aryl-(C C6)alkyl, (C3-C9)Cycloalkyl oder (C3- Cg)Cycloalkyl-(CrC6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist, bedeuten und R12, R13 jeweils unabhängig voneinander(dC 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, nitro, thiocyanato, (CrC 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (C 1 -C 4 ) alkylthio, (Cι-C 4 ) alkylsulfinyl, ( dC 4 ) alkylsulfonyl, (-C-C 4 ) haloalkylsulfinyl, (dC 4 ) haloalkylsulfonyl, (C 3 -Cg) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, heterocyclyl which is unsubstituted or substituted, and Residues of the formulas R'-C (= Z ') -, R'-C (= Z') - Z-, R'-ZC (= Z ') -, R * R "NC (= Z') -, R'-ZC (= Z ') - O-, R'R "NC (= Z , ) -Z-, R'-ZC (= Z , ) -NR" - and R ^' NC ^ -NR '" -, in which R ', R "and R'" each independently of one another hydrogen, (d- C 6 ) alkyl, aryl, aryl- (CC 6 ) alkyl, (C 3 -C 9 ) cycloalkyl or (C 3 - Cg) Cycloalkyl- (CrC6) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, and in which Z and Z 'are each independently an oxygen or sulfur atom, are substituted, and R 12 , R 13 are each independently of one another
Aryl, das unsubstituiert oder substituiert ist, oder (C3-Cg)Cycloalkyl, das unsubstituiert oder substituiert ist, oder Heterocyclyl, das substituiert oder unsubstituiert ist, oderAryl, which is unsubstituted or substituted, or (C 3 -Cg) cycloalkyl, which is unsubstituted or substituted, or heterocyclyl, which is substituted or unsubstituted, or
(Cι-C6)Alkyl, (C2-C6)Alkenyl oder (C2-C6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, Nitro, Thiocyanato, (Cι-C4)Alkoxy, (Cι-C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (d-C4)Alkylthio, (C C4)Alkylsulfonyl, (Cι-C4)Haloalkylsulfinyl, (Cι-C4)Haloalkylsulfonyl, (C3-Cg)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, Heterocyclyl, das unsubstituiert oder substituiert ist, und Reste der Formeln R,-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z,)-I R,R"N-C(=Z')-, R,-Z-C(=Z')-O-, R'R"N-C(=Z')-Z-, R'-Z-C(=Z')-NR"- und R,R"N-C(=Z,)-NRm-, worin R', R" und R'" jeweils unabhängig voneinander Wasserstoff, (d- C6)Alkyl, Aryl, Aryl-(d-C6)alkyl, (C3-C9)Cyc!oalkyl oder (C3- Cg)Cycloalkyl-(Cι-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten und worin Z und Z' unabhängig voneinander jeweils ein Sauerstoff- oder Schwefelatom sind, substituiert ist, bedeuten.(-CC 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, each of the latter 3 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, nitro, Thiocyanato, (-C-C 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (dC 4 ) alkylthio, (CC 4 ) alkylsulfonyl, (-C-C 4 ) haloalkylsulfinyl, (Cι-C 4 ) haloalkylsulfonyl, (C 3 -Cg) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, heterocyclyl which is unsubstituted or substituted and residues of the formulas R , -C (= Z ') -, R'-C (= Z') - Z-, R'-ZC (= Z , ) - I R , R "NC (= Z ' ) -, R , -ZC (= Z ') - O-, R'R "NC (= Z') - Z-, R'-ZC (= Z ') - NR" - and R , R "NC ( = Z , ) -NR m -, wherein R ', R "and R'" each independently of one another hydrogen, (d- C 6 ) alkyl, aryl, aryl- (dC 6 ) alkyl, (C 3 -C 9 ) Cyc oalkyl or (C 3 - Cg) cycloalkyl- (-C-C 6 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, and where Z and Z 'are each independently an oxygen or sulfur atom, substituted, mean.
4. Verbindungen und deren Salze nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass4. Compounds and their salts according to one of claims 1 to 3, characterized in that
R4 Wasserstoff, (d-C4)Alkyl, Phenyl oder (C3-C6)Cycloalkyl, wobei jeder der 3 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (Cι-C4)Alkoxy, (Cι-C4)Haloalkoxy, (C C4)Alkylthio, (CrC4)Haloalkylthio, Mono(Cι-C )alkylamino, Di(Cι-C )alkylamino, (C3-C9)Cycloalkyl, [(d-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(d-C )alkylamino-carbonyl, Di(Cι-C )alkylamino- carbonyl, (Cι-C4)Alkylsulfonyl, (CrC )Haloalkylsulfonyl und im Fall cyclischer Reste auch (Cι-C4)Alkyl und (d-C4)Haloalkyl substituiert ist, oder Formyl, [(CrC4)Alkyl]carbonyi, [(d-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C4)alkylamino-carbonyl oder Di(Cι-C4)alkylamino-carbonyl undR 4 is hydrogen, (dC 4 ) alkyl, phenyl or (C 3 -C 6 ) cycloalkyl, each of the 3 latter radicals being unsubstituted or by one or more radicals from the group consisting of halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl , Cyano, thiocyanato, (-C-C 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (CC 4 ) alkylthio, (CrC 4 ) haloalkylthio, mono (Cι-C) alkylamino, di (Cι-C) alkylamino, ( C 3 -C 9 ) cycloalkyl, [(dC 4 ) alkyl] carbonyl, [(Cι-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (dC) alkylamino-carbonyl, di (Cι-C) alkylamino-carbonyl, (Cι -C 4 ) alkylsulfonyl, (CrC) haloalkylsulfonyl and in the case of cyclic radicals also (-C-C 4 ) alkyl and (dC 4 ) haloalkyl is substituted, or formyl, [(CrC 4 ) alkyl] carbonyi, [(dC 4 ) alkoxy ] carbonyl, aminocarbonyl, mono (-C-C 4 ) alkylamino-carbonyl or di (Cι-C 4 ) alkylamino-carbonyl and
L° eine direkte Bindung oder Sauerstoff,L ° a direct bond or oxygen,
A1 geradkettiges Alkylen mit 1 bis 5 C-Atomen oder geradkettiges Alkenylen oder Alkinylen mit jeweils 2 bis 5 C-Atomen, wobei jeder der drei letztgenannten Diradikale unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Cyano, Thiocyanato und einen Rest der Formel -B2-D2 substituiert ist, worinA 1 straight-chain alkylene with 1 to 5 carbon atoms or straight-chain alkenylene or alkynylene each with 2 to 5 carbon atoms, each of the three last-mentioned diradicals unsubstituted or by one or more radicals from the Halogen, nitro, cyano, thiocyanato and a radical of the formula -B 2 -D 2 is substituted, wherein
B2 eine direkte Bindung oder eine divalente Gruppe der Formeln -O-, -S02-, -CO-, -O-CO-, -NR° -, -NR°-CO-, -CO-NR0-, -O-CO-NR0- oder -NR°-CO-0- bedeuten, in denenB 2 is a direct bond or a divalent group of the formulas -O-, -S0 2 -, -CO-, -O-CO-, -NR ° -, -NR ° -CO-, -CO-NR 0 -, - O-CO-NR 0 - or -NR ° -CO-0- mean in which
R° unabhängig voneinander jeweils Wasserstoff, (Cι-C )Alkyl, Phenyl, Phenyl-(d-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(C1-C4)alkyl, wobei jeder der letztgenannten 5 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfonyl, Cyano, Thiocyanato, (Cι-C4)Alkoxy, (Cι-C4)Haloalkoxy, (d-C4)Alkylthio, (d-C )Haloalkylthio, Mono(Cι-C )alkylamino, Di(C1-C4)alkylamino, (C3-C9)Cycloalkyl, [(d-C4)Alkyl]carbonyl, [(CrC4)Alkoxy]carbonyl, Aminocarbonyl, Mono(CrC4)alkylamino-carbonyl, Di(Cι-C4)alkylamino-carbonyl, (Cι-C4)Alkylsulfonyl, (Cι-C4)Haloalkylsulfonyi und im Fall cyclischer Reste auch (d-d)Alkyl und (Cι-C4)Haloalkyl substituiert ist,R ° independently of one another are each hydrogen, (-CC) alkyl, phenyl, phenyl- (dC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (C 1 -C 4 ) alkyl , wherein each of the last 5 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfonyl, cyano, thiocyanato, (Cι-C 4 ) alkoxy, (Cι-C 4 ) haloalkoxy , (dC 4 ) alkylthio, (dC) haloalkylthio, mono (-C-C) alkylamino, di (C 1 -C 4 ) alkylamino, (C 3 -C 9 ) cycloalkyl, [(dC 4 ) alkyl] carbonyl, [( CrC 4 ) alkoxy] carbonyl, aminocarbonyl, mono (CrC 4 ) alkylamino-carbonyl, di (Cι-C 4 ) alkylamino-carbonyl, (Cι-C 4 ) alkylsulfonyl, (Cι-C 4 ) haloalkylsulfonyi and in the case of cyclic radicals also (dd) alkyl and (-C-C 4 ) haloalkyl is substituted,
A2 eine direkte Bindung oder eine Gruppe der Formel -CH2-, -CH2CH2-,A 2 is a direct bond or a group of the formula -CH 2 -, -CH 2 CH 2 -,
-CH2CH2CH2- oder -CH2CH2CH2CH2-, wobei jeder der 4 letztgenannten Diradikale unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Nitro, Cyano, Thiocyanato und Reste der Formel -B3-D3 substituiert ist, oder einen divalenten Rest der Formel V1, V2, V3, V4 oder V5, -CRaRb-W*-CRcRd - (V1)-CH 2 CH 2 CH 2 - or -CH 2 CH 2 CH 2 CH 2 -, where each of the 4 last-mentioned diradicals is unsubstituted or by one or more radicals from the group halogen, nitro, cyano, thiocyanato and radicals of the formula -B 3 -D 3 is substituted, or a divalent radical of the formula V 1 , V 2 , V 3 , V 4 or V 5 , -CR a R b -W * -CR c R d - (V 1 )
-CRaRb-W*-CRcRd-CReRf- (V2)-CR a R b -W * -CR c R d -CR e R f - (V 2 )
-CRaRb-CRcRd-W*-CReRf- (V3)-CR a R b -CR c R d -W * -CR e R f - (V 3 )
-CRaRb-CRcRd-W*- (V4)-CR a R b -CR c R d -W * - (V 4 )
-CRaRb-W*- (V5) wobei jeder der Reste Ra bis Rf jeweils unabhängig voneinander Wasserstoff, Halogen, Nitro, Cyano, Thiocyanato oder einen Rest der Formel -B4-D4 ist, W* jeweils O, S oder eine Gruppe der Formel N(B5-D5) ist und-CR a R b -W * - (V 5 ) where each of the radicals R a to R f each independently of one another is hydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula -B 4 -D 4 , W * in each case Is O, S or a group of the formula N (B 5 -D 5 ) and
B5 eine direkte Bindung oder eine divalente Gruppe der Formeln -C(=Z*)-,B 5 is a direct bond or a divalent group of the formulas -C (= Z *) -,
-C(=Z*)-Z*% -C(=Z*)-NH- oder -C(=Z*)-NR*-, wobei Z* = O oder S, Z** = O oder S und R* = (d-C4)Alkyl, Phenyl, Phenyl-(C1-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(CrC4)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist,-C (= Z *) - Z *% -C (= Z *) - NH- or -C (= Z *) - NR * -, where Z * = O or S, Z ** = O or S and R * = (dC 4 ) alkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (CrC 4 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted,
B2, B3 und B4 jeweils unabhängig voneinander eine direkte Bindung oder eine divalente Gruppe der Formeln -O-, -S(0)p-, -S(O)p-O-, -O -S(O)p-, -CO-, -O- CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR° -, -O-NR°-, -NR°-0-, -NR°-CO-, -CO-NR0-, -O-CO-NR°- oder -NR°-CO-O-, wobei p die ganze Zahl 0, 1 oder 2 ist und R° = Wasserstoff, (C1-C4)Alkyl, Phenyl, Phenyl-(d-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(C1-C4)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Sulfo, Cyano, Thiocyanato, (Cι-C4)Alkoxy, (Cι-C4)Haloalkoxy, (d-C4)Alkylthio, (Cι-C )Haloalkylthio, Mono(Cι-C4)alkylamino, Di(C C4)alkylamino, (C3-C9)Cycloalkyl, [(C1-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(CrC4)alkylamino-carbonyl, Di(d-C )alkylamino-carbonyl, (CrC4)Alkylsulfonyl, (CrC4)Haloalkylsulfonyl und im Fall cyclischer Reste auch (Cι-C4)Alkyl und (d-C4)Haloalkyl substituiert ist, undB 2 , B 3 and B 4 each independently of one another are a direct bond or a divalent group of the formulas -O-, -S (0) p -, -S (O) p -O-, -O -S (O) p -, -CO-, -O- CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR ° -, -O-NR ° -, -NR ° -0-, -NR ° -CO-, -CO-NR 0 -, -O-CO-NR ° - or -NR ° -CO-O- , where p is the integer 0, 1 or 2 and R ° = hydrogen, (C 1 -C 4 ) alkyl, phenyl, phenyl- (dC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 - C 6 ) Cycloalkyl- (C 1 -C 4 ) alkyl, each of the 5 last-mentioned radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carboxy, sulfo, cyano, thiocyanato, (Cι -C 4 ) alkoxy, (-C-C 4 ) haloalkoxy, (dC 4 ) alkylthio, (Cι-C) haloalkylthio, mono (Cι-C 4 ) alkylamino, di (CC 4 ) alkylamino, (C 3 -C 9 ) Cycloalkyl, [(C 1 -C 4 ) alkyl] carbonyl, [(Cι-C 4 ) alkoxy] carbonyl, aminocarbonyl, mono (CrC 4 ) alkylamino-carbonyl, di (dC) alkylamino-carbonyl, (CrC 4 ) alkylsulfonyl, (CrC 4 ) haloalkylsulfonyl and in the case Cyclic radicals are also substituted (-CC 4 ) alkyl and (dC 4 ) haloalkyl, and
D2, D3, D4 und D5 unabhängig voneinander Wasserstoff, (d-C6)Alkyl, Phenyl,D 2 , D 3 , D 4 and D 5 independently of one another are hydrogen, (dC 6 ) alkyl, phenyl,
Phenyl-(d-C4)alkyl, (C3-C6)Cycloalkyl oder (C3-C6)Cycloalkyl-(d-C6)alkyl, wobei jeder der 5 letztgenannten Reste unsubstituiert oder substituiert ist, bedeuten.Phenyl- (dC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (dC 6 ) alkyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted.
5. Verbindungen und deren Salze nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass5. Compounds and their salts according to one of claims 1 to 4, characterized in that
(X)n n Substituenten X und dabei X vorzugsweise jeweils unabhängig voneinander Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Cyano, Thiocyanato, Aminocarbonyl oder (Cι-C )Alkyl, (Cι-C )Alkoxy, (C1-C4)Alkylthio, Mono(d-C4)alkylamino, Di(d-C4)alky!amino, (C2-C4)Alkenyl, (C2-C4)Alkinyl, [(Cι-C4)Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Mono(Cι-C4)alkylamino- carbonyl, Di(d-C )alkylamino-carbonyl, N-(CrC6)Alkanoyl-amino oder N- (d-C4)Alkanoyl-N-(C1-C4)alkyl-amino, wobei jeder der letztgenannten 13 Reste unsubstituiert oder substituiert ist, vorzugsweise unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Thiocyanato, (d-C4)Alkoxy, (Cι-C4)Haloalkoxy, (d-C4)Alkylthio, . Mono(d-C4)alkylamino, Di(d-C4)alkylamino, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkylamino, [(Cι-C )Alkyl]carbonyl, [(Cι-C4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C )alkylamino- carbonyl, Di(Cι-C4)alkylamino-carbonyl, Phenyl, Phenoxy, Phenylthio, Phenylcarbonyl, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio und Heterocyciylamino, wobei jeder der letztgenannten 8 Reste unsubstituiert ist oder einen oder mehrere Substituenten aus der Gruppe Halogen, Nitro, Cyano, (Cι-C4)Alkyl, (Cι-C4)Alkoxy, (C C4)Alkylthio, (C C4)Haloalkyl, (d-C )Haloalkoxy, Formyl, (Cι-C4)Alkyl-carbonyl und (d-C )Alkoxy- carbonyl aufweist, substituiert ist, oder (C3-C9)Cycloalkyl, Phenyl, Phenoxy, Phenylthio, Phenylcarbonyl, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio oder Heterocyciylamino, wobei jeder der letztgenannten 9 Reste unsubstituiert oder substituiert ist, vorzugsweise unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Nitro, Formyl, Carboxy, Cyano, Thiocyanato, (Cι-C4)Alkyl, (Cι-C )Haloalkyl, (d-C4)Alkoxy, (C1-C4)Haloalkoxy, (CrC4)Alkylthio, (Cι-C4)Haloalkylthio, Mono(Cι-C )alkylamino, Di(d-C )alky!amino, (C3-C6)Cycloalkyl, [(d-C4)Alkyl]carbonyl, [(CrC4)Alkoxy]carbonyl, Aminocarbonyl, Mono(Cι-C )alkylamino-carbonyl und Di(Cι-C4)alkylamino- carbonyl substituiert ist, oder zwei benachbarte Reste X gemeinsam einen ankondensierten Cyclus mit 4 bis 6 Ringatomen, der carbocyclisch ist oder Heteroringatome aus der Gruppe O, S und N enthält und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (Cι-C4)Alkyl und Oxo substituiert ist, und n 0, 1 , 2 oder 3 bedeuten.(X) n n substituents X and X preferably each independently of the other halogen, hydroxy, amino, nitro, formyl, carboxy, cyano, thiocyanato, aminocarbonyl or (Cι-C) alkyl, (Cι-C) alkoxy, (C 1 - C 4 ) alkylthio, mono (dC 4 ) alkylamino, di (dC 4 ) alky! Amino, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, [(C 1 -C 4 ) alkyl] carbonyl, [(-C-C 4 ) alkoxy] carbonyl, mono (Cι-C 4 ) alkylamino-carbonyl, di (dC) alkylamino-carbonyl, N- (CrC 6 ) alkanoyl-amino or N- (dC 4 ) alkanoyl-N- (C 1 -C 4 ) alkylamino, wherein each of the last 13 radicals is unsubstituted or substituted, preferably unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, thiocyanato, (dC 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (dC 4 ) Alkylthio,. Mono (dC 4 ) alkylamino, di (dC 4 ) alkylamino, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkylamino, [(Cι-C) alkyl] carbonyl, [(Cι-C 4 ) alkoxy ] carbonyl, aminocarbonyl, mono (-C-C) alkylamino-carbonyl, di (Cι-C 4 ) alkylamino-carbonyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyciylamino, each of the latter being 8 residues unsubstituted or one or more substituents from the group halogen, nitro, cyano, (-CC 4 ) alkyl, (-C-C 4 ) alkoxy, (CC 4 ) alkylthio, (CC 4 ) haloalkyl, (dC) haloalkoxy, formyl, ( Cι-C 4 ) alkyl-carbonyl and (dC) alkoxy-carbonyl, is substituted, or (C 3 -C 9 ) cycloalkyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyciylamino, each of the latter 9 radicals is unsubstituted or substituted, preferably unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, nitro, formyl, carb oxy, cyano, thiocyanato, (-C-C 4 ) alkyl, (Cι-C) haloalkyl, (dC 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (CrC 4 ) alkylthio, (Cι-C 4 ) haloalkylthio, Mono (-C-C) alkylamino, di (dC) alky! Amino, (C 3 -C 6 ) cycloalkyl, [(dC 4 ) alkyl] carbonyl, [(CrC 4 ) alkoxy] carbonyl, aminocarbonyl, mono (Cι-C ) alkylamino-carbonyl and di (Cι-C 4 ) alkylamino-carbonyl is substituted, or two adjacent radicals X together a fused-on cycle with 4 to 6 ring atoms, which is carbocyclic or contains hetero ring atoms from the group O, S and N and which is unsubstituted or is substituted by one or more radicals from the group halogen, (-CC 4 ) alkyl and oxo, and n is 0, 1, 2 or 3.
6. Verfahren zur Herstellung von Verbindungen der Formel (I) und deren Salzen, wie sie nach einem der Ansprüche 1 bis 5 definiert sind,6. A process for the preparation of compounds of the formula (I) and their salts, as defined in any of claims 1 to 5,
worin A1, A2, L°, R1, R2, R3, R4, X und n wie in Formel (I) in Anspruch 1 definiert sind, dadurch gekennzeichnet, daß manwherein A 1 , A 2 , L °, R 1 , R 2 , R 3 , R 4 , X and n are as defined in formula (I) in claim 1, characterized in that
a) im Falle, dass R3 in Formel (I) eine Gruppe der Formel -L1-N=C(U1)(U3) ist, wobei L1, U1 und U3 wie unter R3 in Formel (I) definiert sind, eine Verbindung der Formel (II),a) in the case that R 3 in formula (I) is a group of the formula -L 1 -N = C (U 1 ) (U 3 ), where L 1 , U 1 and U 3 as under R 3 in formula ( I) are defined, a compound of formula (II),
worin A1, A2, L°, L1, R1, R2, R4, X und n wie in Formel (I) definiert sind, mit einer Verbindung der Formel (III), wherein A 1 , A 2 , L °, L 1 , R 1 , R 2 , R 4 , X and n are as defined in formula (I), with a compound of formula (III),
worin U1 und U3 wie in Formel (I) definiert sind und R18 und R19 unabhängig voneinander jeweils für gegebenenfalls substituiertes Alkyl mit bis zu 12 C-Atomen stehen oder gemeinsam verbunden eine Alkylengruppe mit 2 bis 4 C-Atomen bedeuten, umsetzt oderwherein U 1 and U 3 are as defined in formula (I) and R 18 and R 19 independently of one another each represent optionally substituted alkyl having up to 12 C atoms or, when joined together, denote an alkylene group having 2 to 4 C atoms or
b) im Falle, dass R3 in Formel (I) eine Gruppe der Formel -L1-NG1-C(U2)=N-U4 ist, wobei L1, G1, U2 und U4 wie unter R3 in Formel (I) definiert sind, eine Verbindung der Formel (IV),b) in the case where R 3 in formula (I) is a group of the formula -L 1 -NG 1 -C (U 2 ) = NU 4 , where L 1 , G 1 , U 2 and U 4 are as under R 3 are defined in formula (I), a compound of formula (IV),
worin A1, A2, L°, L1, R1, R2, R4, G1, X und n wie in Formel (I) definiert sind, mit einer Verbindung der Formel (V),wherein A 1 , A 2 , L °, L 1 , R 1 , R 2 , R 4 , G 1 , X and n are as defined in formula (I), with a compound of formula (V),
worin U2 und U4 wie in Formel (I) und R18 wie in Formel (III) in Variante a) dieses Anspruchs definiert sind, umsetzt oderwherein U 2 and U 4 are as defined in formula (I) and R 18 as in formula (III) in variant a) of this claim, or
c) im Falle, dass R3 in Formel (I) eine Gruppe der Formel -L1-N=C(U1)(U3) ist, wobei U3 = NG18NG19G20, NG21OG22 oder NG23SG24 bedeutet und L1, U1, G18, G19, G20, G21, G22, G23, G24 wie unter R3 in Formel (I) definiert sind, eine Verbindung der Formel (VI),c) in the case where R 3 in formula (I) is a group of the formula -L 1 -N = C (U 1 ) (U 3 ), where U 3 = NG 18 NG 19 G 20 , NG 21 OG 22 or NG 23 SG 24 means and L 1 , U 1 , G 18 , G 19 , G 20 , G 21 , G 22 , G 23 , G 24 as defined under R 3 in formula (I), a compound of formula (VI),
worin A1, A2, L°, L1, R1, R2, R4, U1, X und n wie in Formel (I) definiert sind und R6 und R7 wie unter R3 in Formel (I) definiert sind, mit einer Verbindung der Formel (VII) bzw. deren Säureaddukten,wherein A 1 , A 2 , L °, L 1 , R 1 , R 2 , R 4 , U 1 , X and n are as defined in formula (I) and R 6 and R 7 as under R 3 in formula (I ) are defined with a compound of the formula (VII) or its acid adducts,
H-U3 (VII) worin U3 wie in Formel (I) in Anspruch 1 definiert ist, umsetzt oderHU 3 (VII) wherein U 3 is as defined in formula (I) in claim 1, or
d) im Falle, dass R3 in Formel (I) eine Gruppe der Formel -L1-N=C(U1)(U3) ist, wobei L1 wie in Formel (I) definiert ist und U1 = R14 und U3 = R15 bedeuten, wobei R14 und R15 wie unter R3 in Anspruch 3 definiert sind, eine Verbindung der Formel (II) wie in Variante a) dieses Anspruchs definiert mit einem Aldehyd bzw. Keton der Formel (VIII),d) in the event that R 3 in formula (I) is a group of the formula -L 1 -N = C (U 1 ) (U 3 ), where L 1 is as defined in formula (I) and U 1 = R 14 and U 3 = R 15 , where R 14 and R 15 are as defined under R 3 in claim 3, a compound of the formula (II) as defined in variant a) of this claim with an aldehyde or ketone of the formula (VIII )
U1-CO-U3 (VIII) worin U1 und U3 wie in Formel (I) definiert sind, umsetzt.U 1 -CO-U 3 (VIII) in which U 1 and U 3 are as defined in formula (I).
7. Herbizides oder pflanzenwachstumsregulierendes Mittel, dadurch gekennzeichnet, daß es eine oder mehrere Verbindungen der Formel (l) oder deren Salze nach einem der Ansprüche 1 bis 5 und im Pflanzenschutz verwendbare Formulierungshilfsmittel enthält.7. Herbicidal or plant growth-regulating agent, characterized in that it contains one or more compounds of the formula (I) or their salts according to one of Claims 1 to 5 and formulation auxiliaries which can be used in crop protection.
8. Verfahren zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, daß man eine wirksame Menge von einer oder mehreren Verbindungen der Formel (I) oder deren Salzen nach einem der Ansprüche 1 bis 5 auf die Pflanzen, Pflanzensamen oder die Anbaufläche appliziert.8. A method for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the formula (I) or their Salts according to one of claims 1 to 5 applied to the plants, plant seeds or the acreage.
9. Verwendung von Verbindungen der Formel (I) oder deren Salzen nach einem der Ansprüche 1 bis 5 als Herbizide oder Pflanzenwachstumsregulatoren.9. Use of compounds of formula (I) or their salts according to one of claims 1 to 5 as herbicides or plant growth regulators.
10. Verwendung nach Anspruch 9, dadurch gekennzeichnet, daß die Verbindungen der Formel (I) oder deren Salze zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung in Kulturen von Nutz- oder Zierpflanzen eingesetzt werden. 10. Use according to claim 9, characterized in that the compounds of formula (I) or their salts are used to control harmful plants or to regulate growth in crops of useful or ornamental plants.
EP01947437A 2000-07-19 2001-07-03 Substituted 2-amino-1,3,5-triazines, and the use thereof as herbicides and plant growth regulators Withdrawn EP1303498A1 (en)

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