WO1999018082A1 - Novel substituted pyridazinones - Google Patents

Novel substituted pyridazinones Download PDF

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WO1999018082A1
WO1999018082A1 PCT/EP1998/006325 EP9806325W WO9918082A1 WO 1999018082 A1 WO1999018082 A1 WO 1999018082A1 EP 9806325 W EP9806325 W EP 9806325W WO 9918082 A1 WO9918082 A1 WO 9918082A1
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alkyl
carbonyl
alkoxy
hydrogen
substituted
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PCT/EP1998/006325
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German (de)
French (fr)
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Peter Schäfer
Gerhard Hamprecht
Markus Menges
Olaf Menke
Michael Rack
Robert Reinhard
Cyrill Zagar
Peter Münster
Karl-Otto Westphalen
Martina Otten
Helmut Walter
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Basf Aktiengesellschaft
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
    • C07D237/16—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/18—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/22—Nitrogen and oxygen atoms

Definitions

  • the present invention relates to new substituted pyridazinones of the formula I.
  • R ⁇ -R 3 independently of one another hydrogen, nitro, hydroxy, halogen, Ci-C ß -alkoxy, C ⁇ -C 6 -haloalkoxy, SH, Ci-Ce-alkylthio, Ci-Cg-haloalkylthio, amino, Ci-C 6 - Alkylamino, di- (Ci-C ⁇ -alkyl) amino, cyano, Ci-C ⁇ -alkyl, Ci-Cg-haloalkyl , C ⁇ -C 6 alkylsulfinyl, C ⁇ -C 3 alkylsulfonyl, Ci-Ce-haloalkylsulfinyl or Ci-C ⁇ - haloalkylsulfonyl;
  • R 4 , R 5 are hydrogen or, together with the carbon atom to which they are attached, a carbonyl group
  • R 6 is hydrogen, nitro or halogen
  • R 7 is hydrogen, nitro, halogen, COOH, Ci-Cg-alkoxy, (Ci-C ⁇ -alkoxy) carbonyl or (Ci-Cg-alkoxy) carbonyl-Ci-C ß - (alkoxy) carbonyl;
  • R 8 is hydrogen, nitro or QR 8 ';
  • R 8 ' is hydrogen, -CC 6 alkyl, C 3 -C 6 cycloalkyl, Ci-Cg-halogeno-alkyl, cyano- (Ci-Cg-alkyl), -C-C 6 -Al o y-C ⁇ -C 6 -alkyl, -C-C 4 -alkylthio -CC-C 4 -alkyl, -C-C 4 -alkylsulfinyl -CC-C -alkyl, C ⁇ -C 4 -alkylsulfonyl -CC-C 4 -alkyl, C 3 -Cs- alkenyl, Cs-C ⁇ -cyclo- alkenyl, C -CG-haloalkenyl, C3-C6 ⁇ alkynyl, P enyl-C ß alkyl, wherein the phenyl ring one to three sub ⁇ substituents from the group halogen, C ⁇
  • (C 1 -C 4 alkoxy) carbonyl C 1 -C 4 alkoxy, nitro, cyano, COOH and C 1 -C 4 alkoxycarbonyl can carry, carboxyl C 1 -C 4 alkyl,
  • R 9 , R 10 , R 13 , R 15 -R 19 independently of one another are hydrogen or Ci-C ß- alkyl;
  • R 11, R 12 are independently hydrogen, Ci-C ß alkyl, carboxyl, C ⁇ ⁇ C 4 alkyl, (C ⁇ -C 4 alkoxy) carbonyl-C ⁇ -C 4 alkyl, C 6 -C ⁇ 4 -aryl, Phenyl-C ⁇ -C 4 alkyl, or R 11 and R 12 together form a tetramethylene-pentamethylene or ethyleneoxyethylene chain, which is optionally substituted by a carboxyl group or a (C ⁇ -Cg-alkoxy) carbonyl radical;
  • R 14 are hydrogen, C 6 alkyl, carboxyl -C ⁇ -C 6 alkyl, or (Ci-C6 alkoxy) carbonyl -C -C 6 - alkyl;
  • R21 is hydrogen or halogen
  • the invention also relates to the use of the compounds I as herbicides and / or for the desiccation and / or defoliation of plants, herbicidal compositions and agents for the desiccation and / or defoliation of plants which contain the compounds I as active substances,
  • Substituted benzylpyridazinones are from K. Dury et al. , Appl. Chem. 72, 282 (1965), H. Kaj i et al. , Chem. Pharm. Bull. 18, 147 (1970), V. Konecny et al., Coll. Czech Chem. Commun. 5_0, 492 (1985), K. Kaji et al, Chem. Pharm Bull. 3_2, 1423 (1984) and DE-A 42 43 381. Insofar as the compounds described in these documents have a herbicidal activity at all, this is not fully satisfactory in terms of the application rate and crop selectivity.
  • the object of the present invention was therefore to provide new substituted pyridazinones which have good properties as herbicides.
  • the compounds I are also suitable for the desiccation and / or defoliation of parts of plants, for which crop plants such as cotton, potato, rapeseed, sunflower, soybean or field beans, in particular cotton, be considered.
  • crops plants such as cotton, potato, rapeseed, sunflower, soybean or field beans, in particular cotton
  • agents for the desiccation and / or defoliation of plants, methods for producing these agents and methods for the desiccation and / or defoliation of plants with the compounds I have been found.
  • the compounds of the formula I can contain one or more centers of chirality and can then be present as mixtures of enantiomers or diastereomers.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • substituted pyridazinones I can be present in the form of their agriculturally useful salts, the type of salt generally not being important.
  • the salts of such bases and those acid addition salts in which the herbicidal action is not adversely affected in comparison with the free compound I are suitable.
  • Particularly suitable as basic salts are those of the alkali metals, preferably the sodium and potassium salts which the
  • Alkaline earth metals preferably calcium and magnesium salts, those of the transition metals, preferably zinc and iron salts, and ammonium salts, in which the ammonium ion, if desired, one to four C 1 -C 4 -alkyl, hydroxy-C 4 -C 4 -alkyl substituents and / or a phenyl - Can carry benzyl substituents, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl (2-hydroxyethyl) ammonium salts, furthermore phosphonium salts, sulfonium salts such as preferably tri- (C 1 -C 4 alkyl) sulfonium salts, and sulfoxonium salts such as preferably tri- (C 1 -C 4 -alkyl) sulfoxonium salts.
  • benzyl substituents preferably diis
  • acid addition salts are primarily the hydrochlorides and bromides, sulfates, nitrates, phosphates, oxalates or the dodecylbenzenesulfonates.
  • the organic molecule parts mentioned in the definition of R 1 to R 3 and R 8 'to R 19 represent collective terms for individual enumeration of the individual meanings.
  • All carbon chains that is to say all alkyl, haloalkyl, hydroxyalkyl, cyanoalkyl, phenylalkyl, Alkylene, alkoxy, haloalkoxy, hydroxyalkoxy, cyanoalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkyloximino, alkyliminooxy, alkylidene aminoxy, alkenyl, alkenyloxy -, Haloalkenyloxy, alkenylthio, alkynyl, alkynyloxy and alkynylthio parts can be straight-chain or branched. Halogenated
  • -CC 4 alkyl for: CH 3 , C 2 H 5 , CH 2 -C 2 H 5 , CH (CH 3 ) 2 , n-butyl, 1-methylpropyl, 2-methylpropyl or C (CH 3 ) 3 , especially for CH 3 or C 2 H 5 ;
  • haloalkyl for: a C 1 -C 4 -alkyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CH F, CHF 2 , CF 3 , CH 2 C1, CH (C1) 2 , C (CL) 3 , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, CF 5 , 2-fluoropropyl, 3-fluoropropyl, 2-fluoroprop
  • Ci-C ß- alkyl for: C ⁇ -C 4 ⁇ alkyl as mentioned above, and for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethyl-pr ⁇ pyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbityl, 1, 1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1-ethyl-l-methylpropyl or l- Ethyl-2-methylpropyl, in particular for CH 3
  • C ⁇ -C 6 -haloalkyl for: -C-C 6 -alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example one of the radicals mentioned under C 1 -C 4 -haloalkyl or for 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6- Fluoro-l-hexyl, 6-chloro-1-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6, 6, 6-trichloro-l- hexyl or dodecafluorohexyl, in particular for CH 2 F, CHF 2 , CF 3 , CH 2 C1, 2-fluoroethyl, 2-
  • Cyano-C ⁇ -C 6 -alkyl for: for example CH 2 CN, 1-cyanoeth-l-yl, 2-cyanoeth-l-yl, 1-cyano ⁇ rop-l-yl, 2-cyanoprop-l-yl, 3-cyano - prop-1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut -l-yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, l-cyanobut-3-yl, 2-cyano-but-3-yl, l-cyano-2-methyl-prop-3 -yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl or 2-cyanomethyl-prop-2-yl, in particular for CHCN or 2-cyanoethyD-
  • Phenyl-Cx-Cg-alkyl for: e.g. Benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-1-yl, 1-phenylbut-l-yl, 2-phenylbut-l- yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1- (phenylmethyl) -eth-1-yl, 1- (phenylmethyl) -1- (methyl) -eth-l-yl or 1- (phenylmethyl) prop-1-yl, especially for benzyl or 2-phenyl- ethyl;
  • C -C 4 alkoxy for: OCH 3 , OC 2 H 5 , OCH 2 -C 2 H 5 , OCH (CH 3 ) 2 , n-butoxy, 1-methylpropoxy, 2-methylpropoxy or OC (CH 3 ) 3 , especially for OCH 3 or OC 2 H 5 ;
  • Cx-C ß- alkoxy for: C ⁇ -C-alkoxy as mentioned above, and for example n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethyl ⁇ ropoxy, 2, 2 -Dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methyl-pentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2, 2 -Dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and l-ethyl -2-methylpropoxy, especially for OCH 3 , OC 2 Hs or OCH (CH 3 ) 2 ;
  • C ⁇ -C 4 haloalkoxy for: a C ⁇ -C alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example OCH F, OCHF 2 , OCF 3 , 0CH 2 C1, OCH (CD 2 , 0C (C1) 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2,2,2-trifluoroethoxy , 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2, 2, 2-trichloroethoxy, OC 2 F 5 , 2-fluoropropoxy, 3- Fluoropropoxy, 2,2-d
  • C ⁇ -C 6 -haloalkoxy for: a C ⁇ -Cg-alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example one of the radicals mentioned under C ⁇ -C 4 -haloalkoxy or for 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5, 5, 5-trichloro-1-pentoxy, undecafluoropentoxy, 6- Fluoro-l-hexoxy, 6-chloro-l-hexoxy, 6-bromo-l-hexoxy, 6-iodo-l-hexoxy, 6, 6, 6-trichloro-l-hexoxy or dodecafluorohexoxy, especially for OCH 2 F, OCHF, OCF 3 , 0CH 2 C1, 2-fluoroethoxy, 2-chloroethoxy or 2, 2, 2-trifluor
  • C ⁇ -C 6 alkylthio for: SCH 3 , SC 2 H 5 , SCH 2 -C 2 H 5 , SCH (CH 3 ) 2 , n-butylthio, SCH (CH 3 ) -C 2 H 5 , 2- Methylpropylthio, 1, 1-dimethylethylthio, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dirnethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1, 1-dimethylpropylthio, 1, 2- Dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio, 2, 2-dimethyl
  • C ⁇ -C 6 -haloalkyl thio for: C ⁇ -C 6 ⁇ alkylthio as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and or iodine, for example SCH 2 F, SCHF 2 , SCF 3 , SCH 2 C1, SCH (CD 2 , SC (C1) 3 , chlorofluoromethylthio,
  • Dichlorofluoromethylthio chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2, 2, 2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2, 2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2, 2, 2-trichloroethyl hio, SC 2 F 5 , 2-fluoropropylthio, 3-fluoropropylthio, 2, 2-difluoropropylthio, 2,3-di- fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio,
  • C ⁇ -C 6 -alkylsulfinyl for: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethyl-ethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl
  • Cx-C ß- alkylsulfonyl for: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1, 1-dimethyl - ethylsulfonyl, n-pentylsulfonyl, n-pentylsulfonyl Methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2, 2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentyl
  • C ⁇ -C 6 alkylamino for: methylamino, ethylamino, n-propylamino, 1-methylethylamino, n-butylamino, 1-methylpropylamino,
  • 2-methylpropylamino 1, 1-dimethylethylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 1, 1-dimethylpropylamino, 1, 2-dimethylpropylamino, 2,2-dimethylpropylamino, 1-ethylpropyl n-hexylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino,
  • 4-methylpentylamino 1, 1-dimethylbutylamino, 1, 2-dimethylbutylamino, 1, 3-dimethylbutylamino, 2, 2-dimethylbutylamino, 2, 3-dimethylbutylamino, 3, 3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1, 1, 2-trimethylpropylamino, 1, 2, 2-trimethylpropylamino, 1-ethyl-l-methylpropylamino or l-ethyl-2- methylpropylamino, especially for methylamino or ethylamino;
  • Di- (C ⁇ -C 6 -alkyl) amino for: C ⁇ -Cg-alkylamino substituted on the N atom with a Cx-Cg-alkyl group as defined above;
  • C ⁇ -C 6 -Halogenalkylsulfinyl for: C ⁇ -Cg-Alkylsulfinyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, ie where the C ⁇ -C 6 ⁇ alkyl group by a Cx-C ⁇ haloalkyl group as above is replaced, that is, by C C-C 4 haloalkyl as mentioned above or by 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentene, undecafluoropentyl, 6-fluorhexyl or 6-chlorohexyl, in particular chloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;
  • C ⁇ -C 6 -haloalkylsulfonyl for: Cx-C ß -alkylsulfonyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, ie where the C ⁇ -C 6 -alkyl group is replaced by a Cx-Cg-haloalkyl group such as is replaced above, ie by C ⁇ -C 4 haloalkyl as mentioned above or by 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentene, undecafluoropentyl, 6-fluorhexyl or 6-chlorohexyl, in particular chloromethyl, fluoromethyl, di - fluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2, 2-trifluoroethyl;
  • C 3 -C 6 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl or cycl hexyl;
  • C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkyl for: C ⁇ -C ß -alkoxy substituted as mentioned above C ⁇ -Cg-alkyl, for example for CH 2 -OCH 3 , CH 2 -OC 2 H 5 , n -Propoxymethyl, CH 2 -OCH (CH 3 ) 2 , n-butoxymethyl, (l-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1, 1-dimethylethoxy) methyl, 2- (methoxy) ethyl,
  • C ⁇ -C 6 -alkylthio-C-C6 alkyl for: by C ⁇ -C 6 -alkylthio as mentioned above substituted C ⁇ -C6 alkyl, eg CH 2 -SCH 3, CH 2 -SC 2 H 5, n-propylthiomethyl, (1-methylethylthio) methyl, n-butylthiomethyl, (1-methylpropylthio) methyl, (2-methylpropylthio) methyl, (1, 1-dimethylethylthio) methyl, 2-methylhioethyl, 2-ethylthioethyl, 2 - (n-Propylthio) ethyl, 2- (1-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl, 2- (2-methylpropylthio) ethyl, 2- (1, 1 -Dimethyl
  • C ⁇ -C 6 alkylsulfinyl-C ⁇ -C 6 -alkyl of: with C -C e alkylsulphinyl as defined above substituted C ⁇ -C6 ⁇ alkyl as defined above;
  • C ⁇ -C6-alkylsulfonyl-C ⁇ -C 6 -alkyl for: C ⁇ -C6-alkylsulfonyl substituted with C--C 6 -alkyl as defined above;
  • C 3 -C 6 alkenyl for: for example prop-2-en-l-yl, n-buten-4-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop-2- en-l-yl, 2-butene-1-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl-but-2-en-l-yl, 2-methyl-but- 2-en-l-yl, 3-methyl-but-2-en-l-yl, 1-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-but-3-en-1-yl, 1, 1-dimethyl-prop-2-en-1-yl, 1, 2-dimethyl-prop-2-en-1-yl, 1-ethyl prop-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-1-yl, n-hex-5-en-l-yl
  • C 5 -C cycloalkenyl for: cyclopent-1-enyl, cyclopent-2-enyl, cyclopent -3 -enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1- enyl, cyclohept-2-enyl, cyclohept-3-enyl or cyclohept-4-enyl;
  • C 3 -C 6 haloalkenyl for: C 3 -C 6 alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example 2-chloroallyl, 3-chloroallyl, 2, 3-dichloroallyl , 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3 , 3-tribromoallyl or 2,3-dibromobut-2-enyl, in particular for 2-chloroallyl or 3,3-dichlorallyl;
  • C 3 -C 6 alkynyl for: prop-1-in-l-yl, prop-2-in-l-yl, n-but-1-in-l-yl, n-but-l-in-3 -yl, n-but-l-in-4-yl, n-but-2-in-l-yl, n-pent-1-in-l-yl, n-pent-l-in-3-yl , n-pent-1-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl, n Pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-in-l-yl , n-Hex-l-in-3-yl, n-Hex-l-in-4-yl, n-Hex-
  • benzyl 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-l-yl, 1-phenylbut -l-yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2 -yl, 4-phenylbut-2-yl,
  • (C ⁇ -C 6 -alkoxy) carbonyl-C ⁇ -C 6 -alkoxy for: C (-Cg-alkoxy substituted by (C ⁇ -C 6 -alkoxy) carbonyl as mentioned above, for example for methoxycarbonyl-methoxy, ethoxycarbonyl-methoxy, n-propoxycarbonyl-methoxy, n-butoxycarbonyl-methoxy, 1- (methoxycarbonyl) ethoxy, 2- (methoxycarbonyl) ethoxy, 2- (ethoxycarbonyl) ethoxy, 2- (n-propoxycarbonyl) ethoxy, 2- (n-butoxycarbonyl) ethoxy , 3- (methoxycarbonyl) ropoxy, 3- (ethoxycarbonyl) propoxy, 3- (n-propoxycarbonyl) propoxy, 3- (n-butoxycarbonyl) propoxy, 4- (methoxycarbonyl) butoxy, 4- (ethoxycarbony
  • (C ⁇ -C 6 -alkoxy) carbonyl-C ⁇ -C 6 -alkyl for: C (-Cg-alkyl substituted by (C --C 6 -alkoxy) - carbony ⁇ as mentioned above, for example for methoxycarbonyl-methyl, ethoxycarbonyl-methyl , n-propoxycarbonyl-methyl, n-butoxycarbonyl-methyl, 1- (methoxycarbonyl) ethyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 2- (n-propoxycarbonyl) ethyl, 2- (n-butoxycarbonyl) ethyl, 3- (methoxycarbonyl) propyl, 3- (ethoxycarbonyl) propyl, 3- (n-propoxycarbonyl) propyl, 3- (n-butoxycarbonyl) propyl, 4- (methoxycarbonyl) butyl, 4- (eth
  • C ⁇ -C 4 haloalkoxycarbonyl for: a C ⁇ -C 4 alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethoxycarbonyl, dichloromethoxycarbonyl, trichloromethoxycarbonyl, fluoromethoxycarbonyl, difluoromethoxycarbonyl, Trifluoromethoxycarbonyl, chlorofluoromethoxycarbonyl, dichlorofluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2, 2-difluoroethoxycarbonyl, 2,2,2-tri-fluoroethoxycarbonyl, 2 fluoroethoxycarbonyl, 2-chloro-2, 2-difluoroethoxycarbony
  • C ⁇ -C 4 haloalkoxy carbonyl-C ⁇ -C 4 alkyl for: C ⁇ -C 4 alkyl (as defined above, substituted by C ⁇ -C 4 haloalkoxycarbonyl as defined above;
  • C -C 6 cycloalkoxycarbonyl for: cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl or cyclohexyloxycarbonyl;
  • (C ⁇ -C 6 -alkoxy) carbonyl- (C ⁇ -C 6 -alkoxy) carbonyl-C ⁇ -C 6 -alkyl for: (C ⁇ -Cg-alkoxy) carbonyl-C ⁇ -Cg-alkyl (as defined above) substituted by C ⁇ -Cg alkoxycarbonyl as defined above;
  • (C 3 -C 6 alkenyloxy) carbonyl- (C ⁇ -C 6 -alkoxy) carbonyl-C ⁇ -C 6 -alkyl for: (C ⁇ -C 6 -alkoxy) carbonyl-C ⁇ -C 6 -alkyl (as defined above) substituted by C 3 -C 6 alkenyloxycarbonyl (as defined above);
  • Phenoxycarbonyl-C ⁇ -Cg-alkyl for: C ⁇ -Cg-alkyl as defined above, substituted by phenoxycarbonyl; Phenyl- (C ⁇ -Cg-alkoxy) carbonyl for: e.g.
  • benzyloxycarbonyl 1-phenylethoxycarbonyl, 2-phenylethoxycarbonyl, 1-phenyl-prop-1-oxycarbonyl, 2-phenylprop-1-oxycarbonyl, 3-phenyl-prop-1-oxycarbonyl , 1-phenylbut-1-oxycarbonyl, 2-phenylbut-1-oxycarbonyl, 3-phenylbut-1-oxycarbonyl, 4-phenylbut-1-oxycarbonyl, 1-phenylbut-2-oxycarbonyl, 2-phenylbut -2-oxycarbonyl, 3-phenylbut-2-oxycarbonyl, 4-phenylbut-2-oxycarbonyl, 1- (phenylmethyl) -eth-1-oxycarbonyl, 1- (phenylmethyl) -1- (methyl) -eth-1 -oxycarbonyl or 1- (phenylmethyl) prop-1-oxycarbonyl, especially for benzyloxycarbonyl or 2-phenylethoxycarbonyl;
  • Phenyl- (C ⁇ -Cg-alkoxy) carbonyl-C ⁇ -C 6 -alkyl for: C ⁇ -C 6 -alkyl (as defined above) substituted by phenyl- (C ⁇ -Cg-alkoxy) carbonyl as defined above.
  • the variables preferably have the following meanings, individually or in combination:
  • R 1 is hydrogen, halogen, C ⁇ -C 6 alkoxy, C ⁇ -Cg-alkylthio, NH 2 , C ⁇ -Cg-alkylamino or di- (C ⁇ -Cg-alkyl) amino;
  • R 2 is halogen, C ⁇ -Cg-alkyl, C -Cg-haloalkyl, C ⁇ -Cg-alkylthio, C ⁇ -Cg-alkylsulfinyl or C ⁇ -Cg-alkylsulfonyl;
  • R 3 is hydrogen, hydroxy, C ⁇ -Cg-alkyl or C ⁇ -Cg-alkoxy
  • R 8 ' is hydrogen, C ⁇ -C 6 alkyl, C 3 -C 6 cycloalkyl, cyano- (C ⁇ -C 6 alkyl), C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, carboxyl-C ⁇ -C 4 -alkyl, (C -C -alkoxy) carbonyl-C C-C 4 -alkyl, (C -Cg-alkenyloxy) - carbonyl-C ⁇ -C 4 -alkyl, (C 3 -Cg-alkynyloxy) carbonyl-C ⁇ -C 4 - alkyl, C ⁇ -C 4 -alkoxy- (C ⁇ -C 4 -alkoxy) carbonyl-C ⁇ -C 4 -alkyl, (C ⁇ -C 4 -alkoxy) carbonyl- (C ⁇ -C 4 -alkoxy) carbonyl- C ⁇ -C 4 -alkyl, carboxyl-
  • R 9 , R 10 independently of one another are hydrogen or C ⁇ -Cg-alkyl;
  • R 11 , R 12 independently of one another was sers tof f, C ⁇ -Cg-alkyl, carboxyl - C ⁇ -C 4 -alkyl, (C ⁇ -C 4 -alkoxy) carbonyl-C ⁇ -C -alkyl;
  • R 14 C ⁇ -Cg-alkyl
  • R 20 halogen, especially chlorine or bromine
  • R 21 is hydrogen or chlorine.
  • R 1 to R 6 have the abovementioned meaning
  • R 8 is N0
  • R 20 and R 21 independently of one another are hydrogen, CI or bromine
  • R 7 is hydrogen, carboxyl, (C ⁇ -Cg-alkoxy) - carbonyl, (C ⁇ -Cg-alkoxy) carbonyl- (C ⁇ -Cg-alkoxy) carbonyl or C ⁇ -Cg-alkoxy.
  • R 1 for amino, R 2 for C -C 6 alkylthio, C ⁇ -C 3 alkylsulfinyl or C ⁇ -C 6 alkylsulfonyl, R 3 -R 7 for hydrogen and R 8 -R 21 such as are defined above.
  • a further preferred group of compounds are those in which R 1 for amino R 2 for C ⁇ -Cg-alkylthio, C ⁇ -Cg-alkylsulfinyl or C ⁇ -C 5 -alkylsulfonyl, R 3 -R 6 for hydrogen, R 7 for hydrogen, carboxyl, (C ⁇ -Cg-alkoxy) carbonyl, (C ⁇ -Cg-alkoxy) - carbonyl- (C ⁇ -Cg-alkoxy) carbonyl or C ⁇ -Cg-alkoxy, R 8 for N0 2 and R 20 and R 21 independently of one another represent hydrogen, chlorine or bromine.
  • Solvents such as e.g. N, N-dimethylformamide, N-methylpyrrolidone, tetrahydrofuran, dioxane, 1, 2 -diethoxyethane, tert. -Butylmethyl - ether, diethyl ether etc.
  • Suitable bases are, for example, alkali metal carbonates such as sodium carbonate, alkali metal bicarbonates such as sodium bicarbonate and hydroxides such as sodium hydroxide.
  • Nitrogen bases such as triethylamine, dicyclohexylethylamine, pyridine and 4-dimethylaminopyridine can also be used.
  • the reaction temperature is usually in the range from 0 to 100.degree.
  • the components are usually used in approximately stoichiometric amounts, but an excess of one of the components, e.g. with a view to implementing the other component as completely as possible.
  • pyridazinones of the formula II are commercially available, some are known from the literature or can be easily prepared by methods known from the literature.
  • benzyl halides of the formula III are known from the literature or can easily be prepared by methods known from the literature.
  • DE-A 197 11 569.1 describes the preparation of 2,3-dichloro-4-methoxybenzyl bromide by bromomethylation of 2,3-dichloroanisole.
  • the base used can also serve as a solvent, for example in the case of pyridine.
  • Suitable bases are, for example, alkali metal carbonates, hydrogen carbonates and hydroxides, such as NaC0 3 , NaHC0 3 and sodium hydroxide.
  • Nitrogen bases such as triethylamine, dicyclohexylethylamine, pyridine and 4-dimethylamino pyridine can also be used.
  • the reaction can also be carried out in a two-phase mixture, e.g. Toluene and aqueous sodium hydroxide solution are carried out, optionally in the presence of a phase transfer catalyst.
  • a two-phase mixture e.g. Toluene and aqueous sodium hydroxide solution are carried out, optionally in the presence of a phase transfer catalyst.
  • benzoic acid chlorides of the formula IV are known from the literature or can easily be prepared by methods known from the literature.
  • Suitable bases are, for example alkali metal carbonates, bicarbonates and hydroxides such as Na 2 C0 3, NaHCÜ 3 and NaOH into consideration.
  • Nitrogen bases for example triethylamine, dicyclohexylethylamine, pyridine, 4-dimethylamino pyridine, and alkali metal alcoholates such as sodium methylate and sodium ethylate can also be used.
  • the reaction temperature is usually 0 to 100 ° C.
  • the components are usually used in approximately stoichiometric amounts, but an excess of one of the components, e.g. with a view to implementing the other component as completely as possible.
  • alkyl halides of the formula V are commercially available, some are known from the literature or can easily be prepared by methods known from the literature.
  • the substituted benz (o) ylpyridazinones of the formula I in which R 1 is amino or (di) alkylamino and R 2 is C ⁇ -Cg-alkylthio, C ⁇ -Cg-alkylsulfinyl or C ⁇ -Cg-alkylsulfonyl can be from the benz (o) ylpyridazinones of the formula I in which R 1 and R 2 are chlorine, according to the following synthesis scheme 1:
  • Synthesis step 1 is the selective substitution of the chlorine in the 5-position of a 4, 5-dichloro-3 (2H) -pyridazinone by an alkylthio radical. Reactions of this type are generally known, for example from the following literature: K. Dury, Angew. Chem. 7_7, 282 (1965);
  • a polar solvent or solvent mixture cf. JW Lyga, 1988
  • a high dielectric constant for example methanol, ethanol, N, N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran / water, pyridine / Water, methanol / water.
  • the reaction temperature is normally (-10) to + 50 ° C, preferably 0 to 30 ° C.
  • the two components are used in approximately stoichiometric amounts, but a slight excess of one of the components can bring process engineering advantages.
  • Synthesis step 2 is optional and involves the oxidation of the sulfide to the sulfoxide or sulfone. Reactions of this type are generally known, for example from the following literature:
  • Suitable solvents are e.g. Water, sulfuric acid, acetic acid, trifluoroacetic acid or halogenated hydrocarbons such as dichloromethane and chloroform.
  • the oxidation succeeds at temperatures from 0 to 35 100 ° C.
  • the oxidation is to be stopped at the sulfoxide stage, one preferably works with equimolar amounts of the oxidizing agent; if oxidation to the sulfone is desired, at least two equivalents of the oxidizing agent, but better an excess, are used.
  • Synthesis step 3 is the substitution of the chlorine in the 4 position by reaction with ammonia or a (di) alkylamine. Reactions of this type are generally known, for example from the following literature: M. Takaya et al. , Yakugaku Zasshi 9/1530 (1978);
  • reaction can be carried out successfully in a variety of solvents, for example in tetrahydrofuran, tert. Butyl methyl ether, toluene, methanol, ethanol, acetonitrile, N, N-dimethylformamide.
  • substituted pyridazinones I can normally be prepared by the synthesis process mentioned above. For economic or procedural reasons, however, it may be more expedient to prepare some compounds I from similar pyridaziones, but which differ in the meaning of a radical.
  • reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or solvent extraction, or by removing the solvent, distributing the residue in a mixture of water and a suitable one organic solvents and working up the organic phase towards the product. «
  • the substituted pyridazinones I can be obtained in the preparation as isomer mixtures, which, however, if desired, can be separated into the largely pure isomers by the customary methods such as crystallization or chromatography, including on an optically active adsorbate. Pure optically active isomers can advantageously be prepared from corresponding optically active starting products.
  • Agricultural salts of the compounds I can be formed by reaction with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride.
  • Salts of I, the metal ion of which is not an alkali metal ion, can also be prepared in a conventional manner by salting the corresponding alkali metal salt, as can ammonium, phosphonium, sulfonium and sulfoxonium salts using ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
  • the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
  • the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the substituted pyridazinones I are also suitable for the desiccation and / or defoliation of plants.
  • desiccants are particularly suitable for drying out the above-ground parts of crops such as potatoes, rapeseed, sunflower and soybeans. This enables a fully mechanical harvesting of these important crops.
  • the compounds I or the compositions comprising them can be sprayed, atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, sprays or granules. Dusting, scattering or pouring can be used.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives,
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the substrates as such or dissolved in an oil or solvent, by means of wetting agents, adhesives, dispersants or emulsifiers in water be homogenized.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols as well as of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylpheny
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium s
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations contain from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • the following formulation examples illustrate the preparation of such preparations:
  • Wettol ® EM 31 nonionic emulsifier based on ethoxylated castor oil; BASF AG.
  • the active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (as specified), depending on the control target, the season, the target plants and the wax at the stage.
  • the substituted pyridazinones I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • test plants 20 For the purpose of post-emergence treatment, the test plants 20, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers some 25 days before the treatment.
  • the application rate for post-emergence treatment was 0.0625 or 0.0313 kg / ha a.S. (active substance).
  • the plants were kept in a species-specific manner at temperatures of 10 to 30 25 ° C and 20 to 35 ° C.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • 35 was rated on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • the young cotton plants were subjected to runoff (700 1> with the addition of 0.15 wt .-% of the fatty alcohol alkoxylate Plurafac LF ®, based on the spray mixture) sheet treated with aqueous preparations of the active compounds I.
  • the amount of water applied was the equivalent of 1000 l / ha. After 13 days, the number of leaves dropped and the degree of defoliation in% were determined.

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Abstract

The invention relates to substituted pyridazinones of formula (I) and the salts thereof, whereby R1-R3 represent H, NO¿2?, OH, halogen, C1-C6 alkoxyl, C1-C6 haloalkoxyl, SH, C1-C6 alkylthio, C1-C6 haloalkylthio, NH2, C1-C6 alkylamino, Di(C1-C6 alkyl)amino, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkyl sulfinyl, C1-C6 haloalkyl sulfinyl, C1-C6 alkyl sulfonyl, C1-C6 haloalkyl sulfonyl; R?4, R5¿ represent H or, together with the carbon atom on which they are bonded, CO; R6 represents H, NO¿2?, halogen; R?7¿ represents H, NO¿2?, halogen, COOH, C1-C6 alkoxyl, C1-C6 alkoxyl-CO, C1-C6 alkoxyl-CO-(C1-C6 alkoxyl)-CO; R?8¿ represents H, NO¿2?, optionally substituted OH; R?20¿ represents H, halogen for R8 = H or NO¿2?; halogen for R?8¿ = optionally substituted OH; and R21 represents H, halogen. The novel substituted pyridazinones can be used as herbicides for the desiccation/defoliation of plants.

Description

Neue substituierte PyridazinoneNew substituted pyridazinones
Beschreibungdescription
Die vorliegende Erfindung betrifft neue substituierte Pyridazinone der Formel IThe present invention relates to new substituted pyridazinones of the formula I.
Figure imgf000003_0001
Figure imgf000003_0001
in der die Substituenten folgende Bedeutungen haben:in which the substituents have the following meanings:
R^-R3 unabhängig voneinander Wasserstoff, Nitro, Hydroxy, Halogen, Ci-Cß -Alkoxy, Cι-C6-Halogenalkoxy, SH, Ci-Ce-Alkylthio, Ci-Cg-Halogenalkylthio, Amino, Ci-C6-Alkylamino, Di- (Ci-Cβ-alkyl) amino, Cyano, Ci-Cβ-Alkyl, Ci-Cg-Halogenalkyl, Cι-C6-Alkylsulfinyl , Cι-C3-Alkylsulfonyl, Ci-Ce-Halogenalkylsulfinyl oder Ci-Cß-Halogenalkylsulfonyl;R ^ -R 3 independently of one another hydrogen, nitro, hydroxy, halogen, Ci-C ß -alkoxy, Cι-C 6 -haloalkoxy, SH, Ci-Ce-alkylthio, Ci-Cg-haloalkylthio, amino, Ci-C 6 - Alkylamino, di- (Ci-Cβ-alkyl) amino, cyano, Ci-Cβ-alkyl, Ci-Cg-haloalkyl , Cι-C 6 alkylsulfinyl, Cι-C 3 alkylsulfonyl, Ci-Ce-haloalkylsulfinyl or Ci-C β- haloalkylsulfonyl;
R4, R5 Wasserstoff oder gemeinsam zusammen mit dem C-Atom, an das sie gebunden sind, eine Carbonylgruppe;R 4 , R 5 are hydrogen or, together with the carbon atom to which they are attached, a carbonyl group;
R6 Wasserstoff, Nitro oder Halogen;R 6 is hydrogen, nitro or halogen;
R7 Wasserstoff, Nitro, Halogen, COOH, Ci-Cg-Alkoxy, (Ci-Cβ- Alkoxy) carbonyl oder (Ci-Cg-Alkoxy) carbonyl-Ci-Cß- (alkoxy) carbonyl ;R 7 is hydrogen, nitro, halogen, COOH, Ci-Cg-alkoxy, (Ci-Cβ-alkoxy) carbonyl or (Ci-Cg-alkoxy) carbonyl-Ci-C ß - (alkoxy) carbonyl;
R8 Wasserstoff, Nitro oder QR8' ;R 8 is hydrogen, nitro or QR 8 ';
R8' Wasserstoff, Cι-C6-Alkyl, C3-C6-Cycloalkyl, Ci-Cg-Halogen- alkyl, Cyano- (Ci-Cg-Alkyl) , Cι-C6-Al o y-Cι-C6-alkyl, Cι-C4-Alkylthio-Cι-C4-alkyl , Cι-C4-Alkylsulfinyl-Cι-C -alkyl , Cι-C4-Alkylsulfonyl-Cι-C4-alkyl, C3-Cs-Alkenyl , Cs-Cβ-Cyclo- alkenyl, C -Cg-Halogenalkenyl, C3-C6~Alkinyl , P enyl-Ci-Cß-alkyl, wobei der Phenylring ein bis drei Sub¬ stituenten aus der Gruppe Halogen, Cι-C4-Alkyl, Cι-C4-Halo- genalkyl, Hydroxy, Cι-C4-Alkoxy, Cj.-C4-Halogenalkoxy,R 8 'is hydrogen, -CC 6 alkyl, C 3 -C 6 cycloalkyl, Ci-Cg-halogeno-alkyl, cyano- (Ci-Cg-alkyl), -C-C 6 -Al o y-Cι-C 6 -alkyl, -C-C 4 -alkylthio -CC-C 4 -alkyl, -C-C 4 -alkylsulfinyl -CC-C -alkyl, Cι-C 4 -alkylsulfonyl -CC-C 4 -alkyl, C 3 -Cs- alkenyl, Cs-Cβ-cyclo- alkenyl, C -CG-haloalkenyl, C3-C6 ~ alkynyl, P enyl-C ß alkyl, wherein the phenyl ring one to three sub ¬ substituents from the group halogen, Cι- C 4 -alkyl, C 4 -Halo- genalkyl, hydroxy, Cι-C 4 alkoxy, Cj.-C 4 haloalkoxy,
(Cι-C4-Alkoxy) carbonyl-Cι-C4-alkoxy, Nitro, Cyano, COOH und Cι-C4-Alkoxycarbonyl tragen kann, Carboxyl-Cι-C4-.alkyl ,(C 1 -C 4 alkoxy) carbonyl C 1 -C 4 alkoxy, nitro, cyano, COOH and C 1 -C 4 alkoxycarbonyl can carry, carboxyl C 1 -C 4 alkyl,
(Cι-C4-Alkoxy) carbonyl-Cι-C4-alkyl, (C3-C6-Alkenyloxy) - carbonyl-Ci-Ci-alkyl , (C3-C6-Alkinyloxy) carbonyl-Cι-C - alkyl , Cι-C4-Alkoxy- (Cχ-C4-alkoxy) carbonyl-Cι-C4-alkyl , (cι_c 4~Halogenalkoxy) carbonyl-Ci-C4-alkyl , (C -Cg-Cycloalk - oxy) carbonyl-C1-C4-alkyl , (C!-C4-Alko y) carbonyl- (Cι-C4-alk- oxy) carbonyl-Cι-C4-alkyl , (C -Cg-Alkenyloxy) carbonyl- (C3.-C4- alkoxy) carbonyl-Cι-C4-alkyl , (C3-Ce-Alkinyloxy) carbonyl - (Cι-C4-alkoxy) carbonyl-Cι-C4-alkyl , Carboxyl- (Cι-C4-alkoxy) - carbonyl-C!-C4-alkyl , Phenoxycarbonyl-Cι-C4-alkyl , Benzyl - oxycarbonyl-Cι-C4-alkyl ,(-C-C 4 -alkoxy) carbonyl -CC-C 4 -alkyl, (C 3 -C 6 -alkenyloxy) - carbonyl-Ci-Ci-alkyl, (C 3 -C 6 -alkynyloxy) carbonyl -CC-C-alkyl, -C-C 4 -alkoxy- (C (-C 4 -alkoxy) carbonyl-Cι-C 4 -alkyl, ( c ι _c 4 ~ haloalkoxy ) carbonyl-Ci-C 4 -alkyl, (C -Cg-cycloalk-oxy) carbonyl-C 1 -C 4 -alkyl, (C ! -C 4 -alko y) carbonyl- (Cι- C 4 -alkoxy) carbonyl -CC 4 -alkyl, (C -Cg-alkenyloxy) carbonyl- (C 3. -C 4 -alkoxy) carbonyl -CC 4 -alkyl, (C 3 -C e -Alkynyloxy) carbonyl - (-C-C 4 -alkoxy) carbonyl-Cι-C 4 -alkyl, carboxyl- (Cι-C 4 -alkoxy) - carbonyl-C! -C4-alkyl, phenoxycarbonyl-Cι-C 4 -alkyl , Benzyl - oxycarbonyl -CC 4 alkyl,
-CH (R9 ) -CO - OCH (COOR10 ) -COOR10 , -CH (R9 ) -CO-N (R11) R12 , -CH (R9 ) -CO-R13 , -CH (R9 ) C (R13 ) =N-OR14 , -CH (R9 ) -CO-COOR10 , -CH (R9 ) -C (COOR10 ) =N-OR14 , -CH (R9 ) -CO-N [CH (R9 ) -COOR10] -OR14 , "CH (R9 ) -C [-OCH (R9 ) -COOR10] =N-OR14 ,-CH (R 9 ) -CO - OCH (COOR 10 ) -COOR 10 , -CH (R 9 ) -CO-N (R 11 ) R 12 , -CH (R 9 ) -CO-R 13 , -CH ( R 9 ) C (R 13 ) = N-OR 14 , -CH (R 9 ) -CO-COOR 10 , -CH (R 9 ) -C (COOR 10 ) = N-OR 14 , -CH (R 9 ) -CO-N [CH (R 9 ) -COOR 10 ] -OR 14 , " CH (R 9 ) -C [-OCH (R 9 ) -COOR 10 ] = N-OR 14 ,
Figure imgf000004_0001
Figure imgf000004_0001
R9,R10,R13, R15-R19 unabhängig voneinander Wasserstoff oder Ci-Cß-Alkyl;R 9 , R 10 , R 13 , R 15 -R 19 independently of one another are hydrogen or Ci-C ß- alkyl;
R11, R12 unabhängig voneinander Wasserstoff, Ci-Cß-Alkyl, Carboxyl- Cι~C4-alkyl, (Cι-C4-Alkoxy) carbonyl-Cι-C4-alkyl, C6-Cι4-Aryl, Phenyl-Cχ-C4-alkyl, oder R11 und R12 bilden zusammen eine Tetramethylen- Pentamethylen oder Ethylenoxyethylenkette, die ggf. mit einer Carboxylgruppe oder einem (Cχ-Cg-Alk- oxy) carbonylrest substituiert ist;R 11, R 12 are independently hydrogen, Ci-C ß alkyl, carboxyl, Cι ~ C 4 alkyl, (Cι-C 4 alkoxy) carbonyl-Cι-C 4 alkyl, C 6 -Cι 4 -aryl, Phenyl-Cχ-C 4 alkyl, or R 11 and R 12 together form a tetramethylene-pentamethylene or ethyleneoxyethylene chain, which is optionally substituted by a carboxyl group or a (Cχ-Cg-alkoxy) carbonyl radical;
R14 Wasserstoff, Cι-C6-Alkyl, Carboxyl -Cι-C6 -alkyl oder (Ci -C6 -Alkoxy) carbonyl -Ci -C6 - alkyl ;R 14 are hydrogen, C 6 alkyl, carboxyl -Cι-C 6 alkyl, or (Ci-C6 alkoxy) carbonyl -C -C 6 - alkyl;
R20 für R8 = H oder N02 : Wasserstoff oder Halogen; für R8= OR8' : Halogen;R 20 for R 8 = H or N0 2 : hydrogen or halogen; for R 8 = OR 8 ': halogen;
R21 Wasserstoff oder Halogen,R21 is hydrogen or halogen,
sowie die landwirtschaftlich brauchbaren Salze der Verbindungen I,and the agriculturally useful salts of the compounds I,
ausgenommen 4 , 5-Dichlor-2- (4-nitrobenzoyl) -3 (2H) -pyridazinon und 4,5-Dichlor-2- (4-nitrobenzyl) -3 (2H) -pyridazinon. Außerdem betrifft die Erfindung die Verwendung der Verbindungen I als Herbizide und/oder zur Desikkation und/oder Defoliation von Pflanzen, herbizide Mittel und Mittel zur Desikkation und/oder Defoliation von Pflanzen, welche die Verbindungen I als wirksame Substanzen enthalten,except 4,5-dichloro-2- (4-nitrobenzoyl) -3 (2H) pyridazinone and 4,5-dichloro-2- (4-nitrobenzyl) -3 (2H) pyridazinone. The invention also relates to the use of the compounds I as herbicides and / or for the desiccation and / or defoliation of plants, herbicidal compositions and agents for the desiccation and / or defoliation of plants which contain the compounds I as active substances,
Verfahren zur Herstellung der Verbindungen I und von herbiziden Mitteln und Mitteln zur Desikkation und/oder Defoliation von Pflanzen unter Verwendung der Verbindungen I, sowieProcess for the preparation of the compounds I and of herbicidal agents and agents for the desiccation and / or defoliation of plants using the compounds I, and
Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs und zur Desikkation und/oder Defoliation von Pflanzen mit den Verbindungen I .Process for controlling undesirable plant growth and for desiccating and / or defoliation of plants with the compounds I.
Aus der DE-A 195 20 613 ist bekannt, daß bestimmte 2-Phenyl- pyridazinone herbizide Eigenschaften aufweisen; das bekannteste Produkt ist das unter dem Handelsnamen Pyramin bekannte Herbizid Chloridazon.From DE-A 195 20 613 it is known that certain 2-phenylpyridazinones have herbicidal properties; the best known product is the herbicide Chloridazon known under the trade name Pyramin.
Substituierte Benzylpyridazinone sind aus K. Dury et al . , Angew. Chem. 72, 282 (1965), H. Kaj i et al . , Chem. Pharm. Bull. 18, 147 (1970), V. Konecny et al., Coll. Czech Chem. Commun. 5_0, 492 (1985), K. Kaji et al , Chem. Pharm Bull. 3_2, 1423 (1984) und der DE-A 42 43 381 bekannt. Soweit die in diesen Schriften be- schriebenen Verbindungen überhaupt eine herbizide Wirksamkeit aufweisen, vermag diese hinsichtlich Aufwandmenge und Kulturpflanzenselektivität nicht in vollem Umfang zufriedenzustellen.Substituted benzylpyridazinones are from K. Dury et al. , Appl. Chem. 72, 282 (1965), H. Kaj i et al. , Chem. Pharm. Bull. 18, 147 (1970), V. Konecny et al., Coll. Czech Chem. Commun. 5_0, 492 (1985), K. Kaji et al, Chem. Pharm Bull. 3_2, 1423 (1984) and DE-A 42 43 381. Insofar as the compounds described in these documents have a herbicidal activity at all, this is not fully satisfactory in terms of the application rate and crop selectivity.
Aus Farmaco 4_8, 1427 (1993) sind substituierte Benzoylpyridazi - none, insbesondere das 4 , 5-Dichlor-2- (4-nitrobenzoyl) -3 (2H) -pyri - dazinon bekannt. Über eine herbizide Wirkung der Verbindungen finden sich in dieser Schrift keine Angaben.Substituted benzoylpyridazi-none, in particular 4, 5-dichloro-2- (4-nitrobenzoyl) -3 (2H) -pyridazine, are known from Farmaco 4_8, 1427 (1993). There is no information in this document about the herbicidal activity of the compounds.
Aufgabe der vorliegenden Erfindung war es daher, neue substi- tuierte Pyridazinone zur Verfügung zu stellen, die gute Eigenschaften als Herbizide aufweisen.The object of the present invention was therefore to provide new substituted pyridazinones which have good properties as herbicides.
Diese Aufgabe wurde erfindungsgemäß mit den eingangs definierten Verbindungen der Formel I gelöst.This object was achieved according to the invention with the compounds of the formula I defined at the outset.
Bevorzugte Verbindungen der Formel I sind den Unteransprüchen 2 - 5 zu entnehmen.Preferred compounds of the formula I can be found in subclaims 2-5.
Des weiteren wurde gefunden, daß die Verbindungen I auch zur Desikkation und/oder Defoliation von Pflanzenteilen geeignet sind, wofür Kulturpflanzen wie Baumwolle, Kartoffel, Raps, Sonnenblume, Sojabohne oder Ackerbohnen, insbesondere Baumwolle, in Betracht kommen. Diesbezüglich wurden Mittel zur Desikkation und/oder Defoliation von Pflanzen, Verfahren zur Herstellung dieser Mittel und Verfahren zur Desikkation und/oder Defoliation von Pflanzen mit den Verbindungen I gefunden.Furthermore, it was found that the compounds I are also suitable for the desiccation and / or defoliation of parts of plants, for which crop plants such as cotton, potato, rapeseed, sunflower, soybean or field beans, in particular cotton, be considered. In this regard, agents for the desiccation and / or defoliation of plants, methods for producing these agents and methods for the desiccation and / or defoliation of plants with the compounds I have been found.
Die Verbindungen der Formel I können je nach Substi utionsmuster ein oder mehrere Chiralitätszentren enthalten und können dann als Enantiomeren- oder Diastereomerengemische vorliegen. Gegenstand der Erfindung sind sowohl die reinen Enantiomeren oder Diastereomeren als auch deren Gemische.Depending on the substitution pattern, the compounds of the formula I can contain one or more centers of chirality and can then be present as mixtures of enantiomers or diastereomers. The invention relates both to the pure enantiomers or diastereomers and to their mixtures.
Die substituierten Pyridazinone I können in Form ihrer landwirtschaftlich brauchbaren Salze vorliegen, wobei es auf die Art des Salzes in der Regel nicht ankommt. Im allgemeinen kommen die Salze von solchen Basen und diejenigen Säureadditionssalze in Betracht, bei denen die herbizide Wirkung im Vergleich zu der freien Verbindung I nicht negativ beeinträchtigt ist.The substituted pyridazinones I can be present in the form of their agriculturally useful salts, the type of salt generally not being important. In general, the salts of such bases and those acid addition salts in which the herbicidal action is not adversely affected in comparison with the free compound I are suitable.
Als basische Salze eignen sich besonders diejenigen der Alkali - metalle, vorzugsweise die Natrium- und Kaliumsalze, die derParticularly suitable as basic salts are those of the alkali metals, preferably the sodium and potassium salts which the
Erdalkalimetalle, vorzugsweise Calcium- und Magnesiumsalze, die der Übergangsmetalle, vorzugsweise Zink- und Eisensalze, sowie Ammoniumsalze, bei denen das Ammoniumion gewünschtenfalls ein bis vier Cι-C4-Alkyl-, Hydroxy-Cχ-C4-alkylsubstituenten und/oder einen Phenyl- oder Benzylsubstituenten tragen kann, vorzugsweise Diiso- propylammonium-, Tetramethylammonium-, Tetrabutylammonium-, Tri- methylbenzylammonium- und Trimethyl- (2-hydroxyethyl) -ammoniumsalze, des weiteren Phosphoniumsalze, Sulfoniumsalze wie vorzugsweise Tri- (Cι-C4-alkyl) sulfoniumsalze, und Sulfoxoniumsalze wie vorzugsweise Tri- (Cι-C4-alkyl) sulfoxoniumsalze.Alkaline earth metals, preferably calcium and magnesium salts, those of the transition metals, preferably zinc and iron salts, and ammonium salts, in which the ammonium ion, if desired, one to four C 1 -C 4 -alkyl, hydroxy-C 4 -C 4 -alkyl substituents and / or a phenyl - Can carry benzyl substituents, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl (2-hydroxyethyl) ammonium salts, furthermore phosphonium salts, sulfonium salts such as preferably tri- (C 1 -C 4 alkyl) sulfonium salts, and sulfoxonium salts such as preferably tri- (C 1 -C 4 -alkyl) sulfoxonium salts.
Unter den Säureadditionssalzen sind in erster Linie die Hydro- chloride und -bromide, Sulfate, Nitrate, Phosphate, Oxalate oder die Dodecylbenzolsulfonate zu nennen.Among the acid addition salts are primarily the hydrochlorides and bromides, sulfates, nitrates, phosphates, oxalates or the dodecylbenzenesulfonates.
Die bei der Definition von R1 bis R3 und R8' bis R19 genannten organischen Molekülteile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Bedeutungen dar. Sämtliche Kohlenstoffketten, also alle Alkyl-, Halogenalkyl-, Hydroxyalkyl-, Cyanoalkyl-, Phenylalkyl - , Alkylen-, Alkoxy-, Halogenalkoxy-, Hydroxyalkoxy- , Cyanoalkoxy- , Alkylthio-, Halogenalkylthio, Alkylsulfinyl-, Alkylsulfonyl-, Halogenalkylsulfonyl- , Alkylamino-, Dialkylamino-, Alkyloximino- , Alkyliminooxy- , Alkyliden- aminoxy- , Alkenyl-, Alkenyloxy-, Halogenalkenyloxy- , Alkenyl- thio-, Alkinyl-, Alkinyloxy- und Alkinylthio-Teile können gerad- kettig oder verzweigt sein. Halogenierte Substituenten tragen vorzugsweise ein bis fünf gleiche oder verschiedene Halogenatome. Die Bedeutung Halogen steht jeweils für Fluor, Brom, Chlor oder lod, insbesondere für Fluor oder Chlor.The organic molecule parts mentioned in the definition of R 1 to R 3 and R 8 'to R 19 represent collective terms for individual enumeration of the individual meanings. All carbon chains, that is to say all alkyl, haloalkyl, hydroxyalkyl, cyanoalkyl, phenylalkyl, Alkylene, alkoxy, haloalkoxy, hydroxyalkoxy, cyanoalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkyloximino, alkyliminooxy, alkylidene aminoxy, alkenyl, alkenyloxy -, Haloalkenyloxy, alkenylthio, alkynyl, alkynyloxy and alkynylthio parts can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms. Halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
Ferner stehen beispielsweise:Furthermore, for example:
Cι-C4-Alkyl für: CH3 , C2H5 , CH2-C2H5, CH(CH3)2, n-Butyl, 1-Methylpropyl, 2-Methylpropyl oder C(CH3)3, insbesondere für CH3 oder C2H5;-CC 4 alkyl for: CH 3 , C 2 H 5 , CH 2 -C 2 H 5 , CH (CH 3 ) 2 , n-butyl, 1-methylpropyl, 2-methylpropyl or C (CH 3 ) 3 , especially for CH 3 or C 2 H 5 ;
- Cι-C4-Halogenalkyl für: einen Cι_-C4-Alkylrest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. CH F, CHF2, CF3, CH2C1, CH(C1)2, C(CL)3, Chlorfluormethyl, Dichlorfluormethyl, Chlordifluormethyl, 2-Fluorethyl , 2-Chlorethyl, 2-Bromethyl, 2-Iodethyl, 2 , 2-Difluorethyl , 2 , 2 , 2-Trifluorethyl, 2-Chlor- 2-fluorethyl, 2-Chlor-2 , 2-difluorethyl , 2 , 2-Dichlor-2-fluorethyl, 2,2,2-Trichlorethyl, C F5, 2-Fluorpropyl , 3-Fluorpro- pyl, 2, 2-Difluorpropyl, 2 , 3-Difluorpropyl , 2-Chlorpropyl, 3-Chlorproρyl, 2 , 3-Dichlorpropyl , 2-Brompropyl , 3-Brompropyl, 3, 3, 3-Trifluorpropyl, 3 , 3 , 3-Trichlorpropyl , CH2-C2F5,-C 1 -C 4 haloalkyl for: a C 1 -C 4 -alkyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CH F, CHF 2 , CF 3 , CH 2 C1, CH (C1) 2 , C (CL) 3 , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, CF 5 , 2-fluoropropyl, 3-fluoropropyl, 2 , 2-difluoropropyl, 2, 3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2, 3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3, 3, 3-trifluoropropyl, 3, 3, 3-trichloropropyl, CH 2 -C 2 F 5 ,
CF2-C2F5/ 1- (Fluormethyl) -2-fluorethyl, 1- (Chlormethyl) -2- chlorethyl, 1- (Brommethyl) -2-bromethyl, 4-Fluorbutyl, 4-Chlorbutyl, 4-Brombutyl oder Nonafluorbutyl, insbesondere für CH2F, CHF2, CF3, CH2C1, 2-Fluorethyl , 2-Chlorethyl oder 2, 2, 2-Trifluorethyl;CF 2 -C 2 F 5 / 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or Nonafluorobutyl, in particular for CH 2 F, CHF 2 , CF 3 , CH 2 C1, 2-fluoroethyl, 2-chloroethyl or 2, 2, 2-trifluoroethyl;
Ci-Cß-Alkyl für: Cχ-C4~Alkyl wie vorstehend genannt, sowie z.B. n-Pentyl, 1-Methylbutyl, 2-Methylbutyl , 3-Methylbutyl, 2,2-Dimethylpropyl, 1-Ethylpropyl , n-Hexyl, 1, 1-Dimethyl - prσpyl, 1, 2-Dimethylpropyl, 1-Methylpentyl, 2-Methylpentyl , 3-Methylpentyl, 4-Methylpentyl , 1, 1-Dimethylbutyl , 1,2-Dimethylbutyl, 1, 3-Dimethylbutyl , 2 , 2-Dimethylbutyl , 2,3-Dimethylbutyl, 3 , 3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbityl, 1, 1, 2-Trimethylpropyl , 1, 2 , 2-Trimethylpropyl, 1-Ethyl-l-methylpropyl oder l-Ethyl-2-methylpropyl, insbesondere für CH3, C2H5 , CH2-C2H5, CH(CH3)2, n-Butyl, C(CH3)3, n-Pentyl oder n-Hexyl;Ci-C ß- alkyl for: Cχ-C 4 ~ alkyl as mentioned above, and for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethyl-prσpyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbityl, 1, 1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1-ethyl-l-methylpropyl or l- Ethyl-2-methylpropyl, in particular for CH 3 , C 2 H 5 , CH 2 -C 2 H 5 , CH (CH 3 ) 2 , n-butyl, C (CH 3 ) 3 , n-pentyl or n-hexyl;
Cχ-C6-Halogenalkyl für: Cι-C6-Alkyl wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. einen der unter Cι~C4-Halogenalkyl genannten Reste oder für 5-Fluor-l-pentyl , 5-Chlor-l-pentyl, 5-Brom-l-pentyl, 5-Iod-l-pentyl, 5,5,5-Tri- chlor-1-pentyl, Undecafluorpentyl, 6-Fluor-l-hexyl, 6-Chlor- 1-hexyl, 6-Brom-l-hexyl , 6-Iod-l-hexyl , 6 , 6 , 6-Trichlor-l- hexyl oder Dodecafluorhexyl, insbesondere für CH2F, CHF2, CF3, CH2C1, 2-Fluorethyl, 2-Chlorethyl oder 2 , 2 , 2-Trifluorethyl;Cχ-C 6 -haloalkyl for: -C-C 6 -alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example one of the radicals mentioned under C 1 -C 4 -haloalkyl or for 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6- Fluoro-l-hexyl, 6-chloro-1-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6, 6, 6-trichloro-l- hexyl or dodecafluorohexyl, in particular for CH 2 F, CHF 2 , CF 3 , CH 2 C1, 2-fluoroethyl, 2-chloroethyl or 2, 2, 2-trifluoroethyl;
Cyano-Cχ-C6-alkyl für: z.B. CH2CN, 1-Cyanoeth-l-yl, 2-Cyanoeth-l-yl, 1-Cyanoρrop-l-yl , 2-Cyanoprop-l-yl, 3-Cyano- prop-1-yl, l-Cyanoprop-2-yl, 2-Cyanoprop-2-yl , 1-Cyanobut- 1-yl, 2-Cyanobut-l-yl, 3-Cyanobut-l-yl, 4-Cyanobut-l-yl, l-Cyanobut-2-yl, 2-Cyanobut-2-yl , l-Cyanobut-3-yl, 2-Cyano- but-3-yl, l-Cyano-2-methyl-prop-3-yl, 2-Cyano-2-methyl- prop-3-yl, 3-Cyano-2-methyl-prop-3-yl oder 2-Cyanomethyl- prop-2-yl, insbesondere für CHCN oder 2 -CyanoethyD-Cyano-Cχ-C 6 -alkyl for: for example CH 2 CN, 1-cyanoeth-l-yl, 2-cyanoeth-l-yl, 1-cyanoρrop-l-yl, 2-cyanoprop-l-yl, 3-cyano - prop-1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut -l-yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, l-cyanobut-3-yl, 2-cyano-but-3-yl, l-cyano-2-methyl-prop-3 -yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl or 2-cyanomethyl-prop-2-yl, in particular for CHCN or 2-cyanoethyD-
Phenyl-Cx-Cg-alkyl für: z.B. Benzyl, 1-Phenylethyl , 2-Phenyl- ethyl, 1-Phenylprop-l-yl, 2-Phenylprop-l-yl, 3-Phenylprop- 1-yl, 1-Phenylbut-l-yl, 2-Phenylbut-l-yl, 3-Phenylbut-l-yl, 4-Phenylbut-l-yl, l-Phenylbut-2-yl, 2-Phenylbut-2-yl, 3-Phenylbut-2-yl, 4-Phenylbut-2-yl , 1- (Phenylmethyl) -eth- 1-yl, 1- (Phenylmethyl) -1- (methyl) -eth-l-yl oder 1- (Phenylmethyl) -prop-1-yl, insbesondere für Benzyl oder 2-Phenyl- ethyl;Phenyl-Cx-Cg-alkyl for: e.g. Benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-1-yl, 1-phenylbut-l-yl, 2-phenylbut-l- yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1- (phenylmethyl) -eth-1-yl, 1- (phenylmethyl) -1- (methyl) -eth-l-yl or 1- (phenylmethyl) prop-1-yl, especially for benzyl or 2-phenyl- ethyl;
C -C4-Alkoxy für: OCH3, OC2H5, OCH2-C2H5, OCH(CH3)2, n-Butoxy, 1-Methylpropoxy, 2-Methylpropoxy oder OC(CH3)3, insbesondere für OCH3 oder OC2H5;C -C 4 alkoxy for: OCH 3 , OC 2 H 5 , OCH 2 -C 2 H 5 , OCH (CH 3 ) 2 , n-butoxy, 1-methylpropoxy, 2-methylpropoxy or OC (CH 3 ) 3 , especially for OCH 3 or OC 2 H 5 ;
Cx-Cß-Alkoxy für: Cχ-C -Alkoxy wie vorstehend genannt, sowie z.B. n-Pentoxy, 1-Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1, 1-Dimethylpropoxy, 1, 2-Dimethylρropoxy, 2 , 2-Dimethylpropoxy, 1-Ethylpropoxy, n-Hexoxy, 1-Methyl - pentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1, 1-Dimethylbutoxy, 1, 2-Dimethylbutoxy, 1, 3-Dimethylbutoxy, 2, 2-Dimethylbutoxy, 2 , 3-Dimethylbutoxy, 3 , 3-Dimethylbutoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1, 1, 2-Trimethylpropoxy, 1, 2,2-Trimethylpropoxy, 1-Ethyl-1-methylpropoxy und l-Ethyl-2-methylpropoxy, insbesondere für OCH3, OC2Hs oder OCH(CH3)2;Cx-C ß- alkoxy for: Cχ-C-alkoxy as mentioned above, and for example n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylρropoxy, 2, 2 -Dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methyl-pentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2, 2 -Dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and l-ethyl -2-methylpropoxy, especially for OCH 3 , OC 2 Hs or OCH (CH 3 ) 2 ;
Cχ-C4-Halogenalkoxy für: einen Cχ-C -Alkoxyrest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. OCH F, OCHF2 , OCF3, 0CH2C1, OCH (CD 2, 0C(C1)3, Chlorfluormethoxy, Dichlor- fluormethoxy, Chlordifluormethoxy, 2-Fluorethoxy, 2-Chlor- ethoxy, 2-Bromethoxy, 2-Iodethoxy, 2 , 2-Difluorethoxy, 2,2,2-Trifluorethoxy, 2-Chlor-2-fluorethoxy, 2-Chlor-2,2- difluorethoxy, 2 , 2-Dichlor-2-fluorethoxy, 2 , 2 , 2-Trichlor- ethoxy, OC2F5, 2-Fluorpropoxy, 3-Fluorpropoxy, 2,2-Difluor- propoxy, 2 , 3-Difluorpropoxy, 2-Chlorpropoxy, 3-Chlorpropoxy, 2, 3-Dichlorpropoxy, 2-Brompropoxy, 3-Brompropoxy, 3,3,3-Tri- fluorpropoxy, 3 , 3 , 3-Trichlorpropoxy, OCH2-C Fs, OCF -C Fs, 1- (Fluormethyl) -2-fluorethoxy, 1- (Chlormethyl) -2-chlorethoxy, 1- (Brommethyl) -2-bromethoxy, 4-Fluorbutoxy, 4-Chlorbutoxy, 4-Brombutoxy oder Nonafluorbutoxy, insbesondere für 2 -Chlor- ethoxy oder 2, 2, 2 -Trifluorethoxy;Cχ-C 4 haloalkoxy for: a Cχ-C alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example OCH F, OCHF 2 , OCF 3 , 0CH 2 C1, OCH (CD 2 , 0C (C1) 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2,2,2-trifluoroethoxy , 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2, 2, 2-trichloroethoxy, OC 2 F 5 , 2-fluoropropoxy, 3- Fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2, 3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3, 3, 3-trichloropropoxy, OCH 2 -C Fs, OCF -C Fs, 1- (fluoromethyl) -2 -fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, in particular for 2 -chloroethoxy or 2, 2, 2 -Trifluoroethoxy;
Cχ-C6-Halogenalkoxy für: einen Cχ-Cg-Alkoxyrest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. einen der unter Cχ-C4-Halogenalkoxy genannten Reste oder für 5-Fluor-l-pent- oxy, 5-Chlor-l-pentoxy, 5-Brom-l-pentoxy, 5-Iod-l-pentoxy, 5, 5, 5-Trichlor-l-pentoxy, Undecafluorpentoxy, 6-Fluor-l- hexoxy, 6-Chlor-l-hexoxy, 6-Brom-l-hexoxy, 6-Iod-l-hexoxy, 6, 6, 6-Trichlor-l-hexoxy oder Dodecafluorhexoxy, insbesondere für OCH2F, OCHF , OCF3 , 0CH2C1, 2-Fluorethoxy, 2-Chlorethoxy oder 2 , 2 , 2-Trifluorethoxy;Cχ-C 6 -haloalkoxy for: a Cχ-Cg-alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example one of the radicals mentioned under Cχ-C 4 -haloalkoxy or for 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5, 5, 5-trichloro-1-pentoxy, undecafluoropentoxy, 6- Fluoro-l-hexoxy, 6-chloro-l-hexoxy, 6-bromo-l-hexoxy, 6-iodo-l-hexoxy, 6, 6, 6-trichloro-l-hexoxy or dodecafluorohexoxy, especially for OCH 2 F, OCHF, OCF 3 , 0CH 2 C1, 2-fluoroethoxy, 2-chloroethoxy or 2, 2, 2-trifluoroethoxy;
Cχ-C6-Alkylthio für: SCH3 , SC2H5 , SCH2-C2H5, SCH(CH3)2, n-Bu- tylthio, SCH (CH3) -C2H5, 2-Methylpropylthio, 1 , 1-Dimethylethyl - thio, n-Pentylthio, 1-Methylbutylthio, 2-Methylbutylthio, 3-Methylbutylthio, 2 , 2-Dirnethylpropylthio, 1-Ethylpropylthio, n-Hexylthio, 1, 1-Dimethylpropylthio, 1, 2-Dimethylpropylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1, 1-Dime hylbutylthio, 1, 2-Dimethylbutyl - thio, 1, 3-Dimethylbutylthio, 2 , 2-Dimethylbutylthio, 2, 3-Dimethylbutylthio, 3 , 3-Dimethylbutylthio, 1-Ethylbutyl - thio, 2-Ethylbutylthio, 1, 1, 2-Trimethylpropylthio, 1,2,2-Tri- methylpropylthio, 1-Ethyl-l-methylpropylthio und l-Ethyl-2-methylpropylthio, insbesondere für SCH3 oder SCH5;Cχ-C 6 alkylthio for: SCH 3 , SC 2 H 5 , SCH 2 -C 2 H 5 , SCH (CH 3 ) 2 , n-butylthio, SCH (CH 3 ) -C 2 H 5 , 2- Methylpropylthio, 1, 1-dimethylethylthio, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dirnethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1, 1-dimethylpropylthio, 1, 2- Dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2, 3-dimethyl , 3, 3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1, 1, 2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-l-methylpropylthio and l-ethyl-2-methylpropylthio , especially for SCH 3 or SCH 5 ;
Cχ-C6-Halσgenalkylthio für: Cχ-C6~Alkylthio wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor, Brom und oder lod substituiert ist, also z.B. SCH2F, SCHF2, SCF3, SCH2C1, SCH (CD 2, SC(C1)3, Chlorfluormethylthio,Cχ-C 6 -haloalkyl thio for: Cχ-C 6 ~ alkylthio as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and or iodine, for example SCH 2 F, SCHF 2 , SCF 3 , SCH 2 C1, SCH (CD 2 , SC (C1) 3 , chlorofluoromethylthio,
Dichlorfluormethylthio, Chlordifluormethylthio, 2-Fluorethyl - thio, 2-Chlorethylthio, 2-Bromethylthio, 2-lodethylthio, 2, 2-Difluorethylthio, 2 , 2 , 2-Trifluorethylthio, 2-Chlor- 2-fluorethylthio, 2-Chlor-2 , 2-difluorethylthio, 2,2-Dichlor- 2-fluorethylthio, 2 , 2, 2-Trichlorethyl hio, SC2F5, 2-Fluor- propylthio, 3-Fluorpropylthio, 2 , 2-Difluorpropylthio, 2,3-Di- fluorpropylthio, 2-Chlorpropylthio, 3-Chlorpropylthio,Dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2, 2, 2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2, 2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2, 2, 2-trichloroethyl hio, SC 2 F 5 , 2-fluoropropylthio, 3-fluoropropylthio, 2, 2-difluoropropylthio, 2,3-di- fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio,
2, 3-Dichlorpropylthio, 2-Brompropylthio, 3-Brompropylthio,2, 3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio,
3, 3, 3-Trifluorpropylthio, 3 , 3 , 3-Trichlorpropylthio, SCH2-C F5, SCF2-C2F5, 1- (Fluormethyl) -2-fluorethylthio, 1- (Chlormethyl) - 2-chlorethylthio, 1- (Brommethyl) -2-bromethylthio, 4-Fluor- butylthio, 4-Chlorbutylthio, 4-Brombutylthio, Nonafluorbutyl- thio, 5-Fluorpentyl hio, 5-Chlorpentylthio, 5-Brompentylthio, 5-Iodpentylthio, Undecafluorpentylthio, 6-Fluorhexylthio oder 6-Chlorhexylthio, insbesondere für SCH2F, SCHF2 , SCF3, SCH2C1, 2 -Fluorethylthio, 2-Chlorethylthio oder 2 , 2 , 2-Trifluorethyl - thio;3, 3, 3-trifluoropropylthio, 3, 3, 3-trichloropropylthio, SCH 2 -CF 5 , SCF 2 -C 2 F 5 , 1- (fluoromethyl) -2-fluoroethylthio, 1- (chloromethyl) - 2-chloroethylthio, 1- (bromomethyl) -2-bromethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio, nonafluorobutyl- thio, 5-fluoropentyl hio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio or 6-chlorohexylthio, especially for SCH 2 F, SCHF 2 , SCF 3 , SCH 2 C1, 2 -Fluorethylthio, 2 - chloroethylthio or 2, 2, 2-trifluoroethyl - thio;
Cχ-C6-Alkylsulfinyl für: Methylsulfinyl , Ethylsulfinyl , n-Propylsulfinyl, 1-Methylethylsulfinyl, n-Butylsulfinyl, 1-Methylpropylsulfinyl, 2-Methylpropylsulfinyl, 1 , 1-Dimethyl - ethylsulfinyl, n-Pentylsulfinyl , 1-Methylbutylsulfinyl ,Cχ-C 6 -alkylsulfinyl for: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethyl-ethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl
2-Methylbutylsulfinyl, 3-Methylbutylsulfinyl , 1 , 1-Dimethyl - propylsulfinyl, 1, 2-Dimethylpropylsulfinyl , 2 , 2-Dimethyl - propylsulfinyl, 1-Ethylpropylsulfinyl, n-Hexylsulfinyl, 1-Methylpentylsulfinyl, 2-Methylpentylsulfinyl, 3-Methyl- pentylsulfinyl, 4-Methylpentylsulfinyl, 1, 1-Dimethylbutyl- sulfinyl, 1, 2-Dimethylbutylsulfinyl , 1 , 3-Dimethylbutyl - sulfinyl, 2 , 2-Dimethylbutylsulfinyl , 2 , 3-Dimethylbutyl - sulfinyl, 3 , 3-Dimethylbutylsulfinyl , 1-Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, 1,1, 2-Trimethylpropylsulfinyl , 1,2, 2-Trimethylpropylsulfinyl , 1-Ethyl-l-methylpropylsulfinyl oder l-Ethyl-2-methylpropylsulfinyl, insbesondere für SO-CH3;2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3 pentylsulfinyl, 4-methylpentylsulfinyl, 1, 1-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfinyl, 2, 2-dimethylbutylsulfinyl, 2, 3-dimethylbutylsulfinyl, 3, 3-dimethylbutylsulfinyl, 1- Ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1, 2-trimethylpropylsulfinyl, 1,2, 2-trimethylpropylsulfinyl, 1-ethyl-l-methylpropylsulfinyl or l-ethyl-2-methylpropylsulfinyl, especially for SO-CH 3 ;
Cx-Cß-Alkylsulfonyl für: Methylsulfonyl , Ethylsulfonyl, n-Propylsulfonyl, 1-Methylethylsulfonyl, n-Butylsulfonyl, 1-Methylpropylsulfonyl, 2-Methylpropylsulfonyl, 1, 1-Dimethyl - ethylsulfonyl, n-Pentylsulfonyl , 1-Methylbutylsulfonyl, 2-Methylbutylsulfonyl, 3-Methylbutylsulfonyl , 1, 1-Dimethyl - propylsulfonyl, 1 , 2-Dimethylpropylsulfonyl , 2 , 2-Dimethyl - propylsulfonyl , 1-Ethylpropylsulfonyl, n-Hexylsulfonyl , 1-Methylpentylsulfonyl, 2-Methylpentylsulfonyl, 3-Methyl- pentylsulfonyl, 4-Methylpentylsulfonyl, 1, 1-Dimethylbutyl - sulfonyl, 1, 2-Dimethylbutylsulfonyl , 1, 3-Dimethylbutyl - sulfonyl, 2 , 2-Dimethylbutylsulfonyl , 2 , 3-Dimethylbutyl - sulfonyl«» 3 , 3-Dimethylbutylsulfonyl, 1-Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1, 1, 2-Trimethylpropylsulfonyl,Cx-C ß- alkylsulfonyl for: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1, 1-dimethyl - ethylsulfonyl, n-pentylsulfonyl, n-pentylsulfonyl Methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2, 2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonylsulfonyl, 2-methylpentyl, 2-methylpentyl 4-methylpentylsulfonyl, 1, 1-dimethylbutylsulfonyl, 1, 2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2, 2-dimethylbutylsulfonyl, 2, 3-dimethylbutylsulfonyl, 3, 3-dimethylbutylsulfonyl, 1-3 , 2-ethylbutylsulfonyl, 1, 1, 2-trimethylpropylsulfonyl,
1,2, 2-Trimethylpropylsulfonyl, 1-Ethyl-l-methylpropylsulfonyl oder l-Ethyl-2-methylpropylsulfonyl, insbesondere für S02-CH3;1,2, 2-trimethylpropylsulfonyl, 1-ethyl-l-methylpropylsulfonyl or l-ethyl-2-methylpropylsulfonyl, especially for S0 2 -CH 3 ;
Cχ-C6-Alkylamino für: Methylamino, Ethylamino, n-Propylamino, 1-Methylethylamino, n-Butylamino, 1-Methylpropylamino,Cχ-C 6 alkylamino for: methylamino, ethylamino, n-propylamino, 1-methylethylamino, n-butylamino, 1-methylpropylamino,
2-Methylpropylamino, 1, 1-Dimethylethylamino, n-Pentylamino, 1-Methylbutylamino, 2-Methylbutylamino, 3-Methylbutylamino, 1, 1-Dimethylpropylamino, 1, 2-Dimethylpropylamino, 2,2-Dime- thylpropylamino, 1-Ethylpropylamino, n-Hexylamino, 1-Methyl- pentylamino, 2-Methylpentylamino, 3-Methylpentylamino,2-methylpropylamino, 1, 1-dimethylethylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 1, 1-dimethylpropylamino, 1, 2-dimethylpropylamino, 2,2-dimethylpropylamino, 1-ethylpropyl n-hexylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino,
4-Methylpentylamino, 1, 1-Dimethylbutylamino, 1 , 2-Dimethyl - butylamino, 1, 3-Dimethylbutylamino, 2 , 2-Dimethylbutylamino, 2 , 3-Dimethylbutylamino, 3 , 3-Dimethylbutylamino, 1-Ethylbutylamino, 2-Ethylbutylamino, 1, 1, 2-Trimethylpropylamino, 1, 2 , 2-Trimethylpropylamino, 1-Ethyl-l-methylpropylamino oder l-Ethyl-2-methylpropylamino, insbesondere für Methylamino oder Ethylamino;4-methylpentylamino, 1, 1-dimethylbutylamino, 1, 2-dimethylbutylamino, 1, 3-dimethylbutylamino, 2, 2-dimethylbutylamino, 2, 3-dimethylbutylamino, 3, 3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1, 1, 2-trimethylpropylamino, 1, 2, 2-trimethylpropylamino, 1-ethyl-l-methylpropylamino or l-ethyl-2- methylpropylamino, especially for methylamino or ethylamino;
Di- (Cχ-C6-alkyl) amino für: am N-Atom mit einer Cx-Cg-Alkyl- gruppe wie vorstehend definiert substituiertes Cχ-Cg-Alkyl- amino ;Di- (Cχ-C 6 -alkyl) amino for: Cχ-Cg-alkylamino substituted on the N atom with a Cx-Cg-alkyl group as defined above;
Cχ-C6-Halogenalkylsulfinyl für: Cχ-Cg-Alkylsulfinyl wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor und/oder Brom substituiert ist, d.h. wobei die Cχ-C6~ Alkylgruppe durch eine Cx-Cς-Halogenalkylgruppe wie vorstehend genannt ersetzt ist, also durch Cχ-C4-Halogenalkyl wie vorstehend genannt oder durch 5-Fluorpentyl , 5-Chlorpentyl, 5-Brom- pentyl, 5-Iodpenty, Undecafluorpentyl , 6-Fluorhexyl oder 6-Chlorhexyl, insbesondere Chlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, 2-Fluorethyl , 2-Chlorethyl oder 2,2,2-Trifluorethyl ;Cχ-C 6 -Halogenalkylsulfinyl for: Cχ-Cg-Alkylsulfinyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, ie where the Cχ-C 6 ~ alkyl group by a Cx-Cς haloalkyl group as above is replaced, that is, by C C-C 4 haloalkyl as mentioned above or by 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentene, undecafluoropentyl, 6-fluorhexyl or 6-chlorohexyl, in particular chloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;
Cχ-C6-Halogenalkylsulfonyl für: Cx-Cß-Alkylsulfonyl wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor und/oder Brom substituiert ist, d.h. wobei die Cχ-C6-Alkylgruppe durch eine Cx-Cg-Halogenalkylgruppe wie vorstehend genannt ersetzt ist, also durch Cχ-C4-Halogenalkyl wie vorstehend genannt oder durch 5-Fluorpentyl, 5-Chlorpentyl, 5-Brompentyl, 5-Iodpenty, Undecafluorpentyl, 6-Fluorhexyl oder 6-Chlorhexyl, insbesondere Chlormethyl, Fluormethyl, Di- fluormethyl, Trifluormethyl , 2-Fluorethyl , 2-Chlorethyl oder 2,2, 2-Trifluorethyl ;Cχ-C 6 -haloalkylsulfonyl for: Cx-C ß -alkylsulfonyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, ie where the Cχ-C 6 -alkyl group is replaced by a Cx-Cg-haloalkyl group such as is replaced above, ie by Cχ-C 4 haloalkyl as mentioned above or by 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentene, undecafluoropentyl, 6-fluorhexyl or 6-chlorohexyl, in particular chloromethyl, fluoromethyl, di - fluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2, 2-trifluoroethyl;
C3-C6-Cycloalkyl für: Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cycl hexyl;C 3 -C 6 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl or cycl hexyl;
Cχ-C6-Alkoxy-Cχ-C6-alkyl für: durch Cx-Cß-Alkoxy wie vorstehend genannt substituiertes Cχ-Cg-Alkyl, also z.B. für CH2-OCH3, CH2-OC2H5, n-Propoxymethyl , CH2-OCH (CH3) 2 , n-Butoxy- methyl, (l-Methylpropoxy)methyl, (2-Methylpropoxy) methyl, (1, 1-Dimethylethoxy) methyl, 2- (Methoxy) ethyl,Cχ-C 6 -alkoxy-Cχ-C 6 -alkyl for: Cχ-C ß -alkoxy substituted as mentioned above Cχ-Cg-alkyl, for example for CH 2 -OCH 3 , CH 2 -OC 2 H 5 , n -Propoxymethyl, CH 2 -OCH (CH 3 ) 2 , n-butoxymethyl, (l-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1, 1-dimethylethoxy) methyl, 2- (methoxy) ethyl,
2- (Ethoxy) ethyl, 2- (n-Propoxy) ethyl , 2- (1-Methylethoxy) ethyl , 2- (n-Butoxy) ethyl, 2- (1-Methylpropoxy) ethyl , 2-(2-Methyl- propoxy) ethyl, 2- (1, 1-Dimethylethoxy) ethyl, 2- (Methoxy) propyl, 2- (Ethoxy) propyl , 2- (n-Propoxy) ropyl, 2- (1-Methylethoxy) propyl, 2- (n-Butoxy) propyl, 2-(l-Methyl- propoxy) propyl, 2- (2-Methylpropoxy) ropyl, 2- (1, 1-Dimethyl - ethoxy) propyl, 3- (Methoxy) propyl , 3- (Ethoxy) propyl , 3- (n-Propoxy) propyl, 3- (1-Methylethoxy) propyl, 3- (n-Butoxy) propyl, 3- (1-Methylpropoxy) propyl, 3- (2-Methylprop- oxy) ropyl, 3- (1, 1-Dimethylethoxy) ropyl, 2- (Methoxy) - butyl, 2- (Ethoxy) butyl, 2- (n-Propoxy) butyl , 2- (1-Methyl- ethoxy) butyl, 2- (n-Butoxy) butyl, 2- (1-Methylpropoxy) butyl, 2- (2-Methylpropoxy) butyl, 2- (1, 1-Dimethylethoxy) butyl , 3- (Methoxy) butyl, 3- (Ethoxy) butyl , 3- (n-Propoxy) butyl , 3-(l-Methylethoxy)butyl, 3- (n-Butoxy) butyl, 3-(l-Methyl- propoxy) butyl , 3- (2-Methylpropoxy)butyl, 3- (1, 1-Dimethyl - ethoxy)butyl, 4- (Methoxy) butyl , 4- (Ethoxy) butyl, 4- (n-Propoxy) butyl, 4- (1-Methylethoxy) butyl, 4- (n-Butoxy) butyl , 4- (l-Methylpropoxy) butyl, 4- (2-Methylpropoxy) butyl oder 4- (1, 1-Dimethylethoxy) butyl, insbesondere für CH -OCH3 oder 2 -Methoxyethyl ;2- (ethoxy) ethyl, 2- (n-propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methyl- propoxy) ethyl, 2- (1, 1-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (n-propoxy) ropyl, 2- (1-methylethoxy) propyl, 2- ( n-butoxy) propyl, 2- (l-methylpropoxy) propyl, 2- (2-methylpropoxy) ropyl, 2- (1, 1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy ) propyl, 3- (n-propoxy) propyl, 3- (1-methylethoxy) propyl, 3- (n-butoxy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methylpropoxy) ropyl, 3- ( 1, 1-dimethylethoxy) ropyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n-propoxy) butyl, 2- (1-methylethoxy) butyl, 2- (n-butoxy) butyl, 2- (1-methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- (1, 1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (n- Propoxy) butyl, 3- (1-methylethoxy) butyl, 3- (n-butoxy) butyl, 3- (1-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- (1, 1-dimethyl - ethoxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (n-propoxy) butyl, 4- (1-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (l -Methylpropoxy) butyl, 4- (2-methylpropoxy) butyl or 4- (1, 1-dimethylethoxy) butyl, especially for CH -OCH 3 or 2 -methoxyethyl;
Cχ-C6-Alkylthio-C -C6-alkyl für: durch Cχ-C6-Alkylthio wie vorstehend genannt substituiertes Cχ-C6-Alkyl, also z.B. für CH2-SCH3, CH2-SC2H5, n-Propylthiomethyl , (1-Methylethyl - thio) methyl, n-Butylthiomethyl, ( 1-Methylpropylthio) methyl , (2-Methylpropylthio) methyl, (1 , 1-Dimethylethylthio) methyl , 2-Methyl hioethyl, 2-Ethylthioethyl, 2- (n-Propylthio) ethyl , 2- (1-Methylethylthio) ethyl, 2- (n-Butylthio) ethyl, 2- (1-Methylpropylthio) ethyl, 2- (2-Methylpropylthio) ethyl, 2- (1, 1-Dimethylethylthio) ethyl, 2- (Methylthio) propyl , 3- (Methylthio) ropyl, 2- (Ethylthio) propyl , 3- (Ethyl - thio) propyl, 3- (Propylthio) propyl, 3- (Butylthio) propyl, 4- (Methylthio) butyl, 4- (Ethylthio) butyl , 4-(n-Propyl- thio)butyl oder 4- (n-Butylthio) butyl, insbesondere für 2- (Methylthio) ethyl ;Cχ-C 6 -alkylthio-C-C6 alkyl for: by Cχ-C 6 -alkylthio as mentioned above substituted Cχ-C6 alkyl, eg CH 2 -SCH 3, CH 2 -SC 2 H 5, n-propylthiomethyl, (1-methylethylthio) methyl, n-butylthiomethyl, (1-methylpropylthio) methyl, (2-methylpropylthio) methyl, (1, 1-dimethylethylthio) methyl, 2-methylhioethyl, 2-ethylthioethyl, 2 - (n-Propylthio) ethyl, 2- (1-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl, 2- (2-methylpropylthio) ethyl, 2- (1, 1 -Dimethylethylthio) ethyl, 2- (methylthio) propyl, 3- (methylthio) ropyl, 2- (ethylthio) propyl, 3- (ethylthio) propyl, 3- (propylthio) propyl, 3- (butylthio) propyl, 4 - (Methylthio) butyl, 4- (ethylthio) butyl, 4- (n-propylthio) butyl or 4- (n-butylthio) butyl, especially for 2- (methylthio) ethyl;
Cχ-C6-Alkylsulfinyl-Cχ-C6-alkyl für: mit C -Ce-Alkylsulfinyl wie vorstehend definiert substituiertes Cχ-C6~Alkyl wie vorstehend definiert;Cχ-C 6 alkylsulfinyl-Cχ-C 6 -alkyl of: with C -C e alkylsulphinyl as defined above substituted Cχ-C6 ~ alkyl as defined above;
Cχ-C6-Alkylsulfonyl-Cχ-C6-alkyl für: mit Cχ-C6-Alkylsulfonyl wie vorstehend definiert substituiertes Cχ-Cg-Alkyl wie vorstehend definiert;Cχ-C6-alkylsulfonyl-Cχ-C 6 -alkyl for: Cχ-C6-alkylsulfonyl substituted with C--C 6 -alkyl as defined above;
C3-C6-Alkenyl für: z.B. Prop-2-en-l-yl, n-Buten-4-yl, l-Methyl-prop-2-en-l-yl, 2-Methyl-prop-2-en-l-yl , 2-Buten- 1-yl, n-Penten-3-yl, n-Penten-4-yl , 1-Methyl-but-2-en-l-yl , 2-Methyl-but-2-en-l-yl, 3-Methyl-but-2-en-l-yl, 1-Methyl- but-3-en-l-yl, 2-Methyl-but-3-en-l-yl , 3-Methyl-but-3-en- 1-yl, 1, 1-Dimethyl-prop-2-en-l-yl, 1, 2-Dimethyl-prop-2-en- 1-yl, l-Ethyl-prop-2-en-l-yl, n-Hex-3-en-l-yl, n-Hex-4-en- 1-yl, n-Hex-5-en-l-yl, 1-Methyl-pent-3-en-l-yl , 2-Methyl- pent-3-en-l-yl, 3-Methyl-pent-3-en-l-yl, 4-Methyl-pent-3- en-l-yl, l-Methyl-pent-4-en-l-yl, 2-Methyl-pent-4-en-l-yl , 3-Methyl-pent-4-en-l-yl , 4-Methyl-pent-4-en-l-yl , 1, 1-Dimethyl-but-2-en-l-yl , 1, 1-Dimethyl-but-3-en-l-yl , 1 , 2-Dimethyl-but-2-en-l-yl , 1, 2-Dimethyl-but-3-en-l-yl , 1, 3-Dimethyl-but-2-en-l-yl, 1, 3-Dimethyl-but-3-en-l-yl, 2 , 2-Dimethyl-but-3-en-l-yl , 2 , 3-Dimethyl-but-2-en-l-yl , 2 , 3-Dimethyl-but-3-en-l-yl, 3 , 3-Dimethyl-but-2-en-l-yl , l-Ethyl-but-2-en-l-yl, l-Ethyl-but-3-en-l-yl, 2-Ethyl-but-2- en-l-yl, 2-Ethyl-but-3-en-l-yl, 1, 1, 2-Trimethyl-prop-2-en- 1-yl, l-Ethyl-l-methyl-prop-2-en-l-yl oder l-Ethyl-2-methyl- prop-2-en-l-yl, insbesondere für Prop-2 -en- 1 -yl oder n-Buten- 4-yl;C 3 -C 6 alkenyl for: for example prop-2-en-l-yl, n-buten-4-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop-2- en-l-yl, 2-butene-1-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl-but-2-en-l-yl, 2-methyl-but- 2-en-l-yl, 3-methyl-but-2-en-l-yl, 1-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-but-3-en-1-yl, 1, 1-dimethyl-prop-2-en-1-yl, 1, 2-dimethyl-prop-2-en-1-yl, 1-ethyl prop-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-1-yl, n-hex-5-en-l-yl, 1-methyl pent-3-en-l-yl, 2-methyl-pent-3-en-l-yl, 3-methyl-pent-3-en-l-yl, 4-methyl-pent-3- en-l-yl, l-methyl-pent-4-en-l-yl, 2-methyl-pent-4-en-l-yl, 3-methyl-pent-4-en-l-yl, 4- Methyl-pent-4-en-1-yl, 1, 1-dimethyl-but-2-en-1-yl, 1, 1-dimethyl-but-3-en-1-yl, 1, 2-dimethyl but-2-en-l-yl, 1, 2-dimethyl-but-3-en-l-yl, 1, 3-dimethyl-but-2-en-l-yl, 1, 3-dimethyl-but- 3-en-1-yl, 2, 2-dimethyl-but-3-en-1-yl, 2, 3-dimethyl-but-2-en-1-yl, 2, 3-dimethyl-but-3- en-l-yl, 3,3-dimethyl-but-2-en-l-yl, l-ethyl-but-2-en-l-yl, l-ethyl-but-3-en-l-yl, 2-ethyl-but-2-en-1-yl, 2-ethyl-but-3-en-1-yl, 1, 1, 2-trimethyl-prop-2-en-1-yl, 1-ethyl l-methyl-prop-2-en-l-yl or l-ethyl-2-methyl-prop-2-en-l-yl, especially for prop-2 -en-1 -yl or n-butene-4- yl;
C5-C -Cycloalkenyl für: Cyclopent- 1-enyl , Cyclopent-2 -enyl , Cyclopent -3 -enyl, Cyclohex-1-enyl, Cyclohex-2 -enyl, Cyclo- hex-3-enyl, Cyclohept-1-enyl, Cyclohept-2 -enyl , Cyclo- hept-3-enyl oder Cyclohept-4 -enyl ;C 5 -C cycloalkenyl for: cyclopent-1-enyl, cyclopent-2-enyl, cyclopent -3 -enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1- enyl, cyclohept-2-enyl, cyclohept-3-enyl or cyclohept-4-enyl;
C3-C6-Halogenalkenyl für: C3-C6-Alkenyl wie vorstehend genannt, das partiell oder vollständig durch Fluor, Chlor und/oder Brom substituiert ist, also z.B. 2-Chlorallyl , 3-Chlorallyl, 2 , 3-Dichlorallyl , 3 , 3-Dichlorallyl , 2,3,3-Tri- chlorallyl, 2 , 3-Dichlorbut-2-enyl, 2-Bromallyl, 3-Bromallyl, 2 , 3-Dibromallyl, 3 , 3-Dibromallyl , 2, 3 , 3-Tribromallyl oder 2, 3-Dibrombut-2-enyl, insbesondere für 2-Chlorallyl oder 3 , 3 -Dichlorallyl ;C 3 -C 6 haloalkenyl for: C 3 -C 6 alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example 2-chloroallyl, 3-chloroallyl, 2, 3-dichloroallyl , 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3 , 3-tribromoallyl or 2,3-dibromobut-2-enyl, in particular for 2-chloroallyl or 3,3-dichlorallyl;
C3-C6-Alkinyl für: Prop-1-in-l-yl, Prop-2-in-l-yl , n-But-1- in-l-yl, n-But-l-in-3-yl , n-But-l-in-4-yl, n-But-2-in-l-yl , n-Pent-1-in-l-yl, n-Pent-l-in-3-yl , n-Pent-l-in-4-yl , n-Pent- l-in-5-yl, n-Pent-2-in-l-yl , n-Pent-2-in-4-yl , n-Pent-2-in- 5-yl, 3-Methyl-but-l-in-3-yl, 3-Methyl-but-l-in-4-yl, n-Hex- 1-in-l-yl, n-Hex-l-in-3-yl, n-Hex-l-in-4-yl, n-Hex-l-in-5-yl , n-Hex-l-j.n-6-yl, n-Hex-2-in-l-yl , n-Hex-2-in-4-yl , n-Hex-2- in-5-yl, n-Hex-2-in-6-yl, n-Hex-3-in-l-yl , n-Hex-3-in-2-yl, 3-Methyl-pent-l-in-l-yl, 3-Methyl-pent-l-in-3-yl, 3-Methyl- pent-l-in-4-yl, 3-Methyl-ρent-l-in-5-yl , 4-Methyl-pent-1-in- 1-yl, 4-Methyl-pent-2-in-4-yl oder 4-Methyl-pent-2-in-5-yl , insbesondere für Prop-2-in-l-yl; Phenyl- (Cχ-Cδ -alkyl) für: z.B. Benzyl, 1-Phenylethyl , 2-Phenylethyl, 1-Phenylprop-l-yl, 2-Phenylprop-l-yl , 3-Phenylprop-l-yl, 1-Phenylbut-l-yl , 2-Phenylbut-l-yl, 3-Phenylbut-l-yl, 4-Phenylbut-l-yl , l-Phenylbut-2-yl, 2-Phenylbut-2-yl, 3-Phenylbut-2-yl, 4-Phenylbut-2-yl,C 3 -C 6 alkynyl for: prop-1-in-l-yl, prop-2-in-l-yl, n-but-1-in-l-yl, n-but-l-in-3 -yl, n-but-l-in-4-yl, n-but-2-in-l-yl, n-pent-1-in-l-yl, n-pent-l-in-3-yl , n-pent-1-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl, n Pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-in-l-yl , n-Hex-l-in-3-yl, n-Hex-l-in-4-yl, n-Hex-l-in-5-yl, n-Hex-l- j .n-6-yl , n-Hex-2-in-l-yl, n-Hex-2-in-4-yl, n-Hex-2-in-5-yl, n-Hex-2-in-6-yl, n -Hex-3-in-l-yl, n-hex-3-in-2-yl, 3-methyl-pent-l-in-l-yl, 3-methyl-pent-l-in-3-yl , 3-methyl-pent-l-in-4-yl, 3-methyl-pent-l-in-5-yl, 4-methyl-pent-1-in-1-yl, 4-methyl-pent-2 -in-4-yl or 4-methyl-pent-2-in-5-yl, in particular for prop-2-in-l-yl; Phenyl- (Cχ-C δ- alkyl) for: e.g. benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-l-yl, 1-phenylbut -l-yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2 -yl, 4-phenylbut-2-yl,
1- (Phenylmethyl) -eth-l-yl, 1- (Phenylmethyl) -1- (methyl) - eth-l-yl oder 1- (Phenylmethyl) -prop-1-yl , insbesondere für Benzyl oder 2-Phenylethyl;1- (phenylmethyl) -eth-l-yl, 1- (phenylmethyl) -1- (methyl) -eth-l-yl or 1- (phenylmethyl) prop-1-yl, especially for benzyl or 2-phenylethyl;
(Cχ-C4 -Alkoxy) carbonyl für: COOCH3 , COOC2H5, COOCH2-CH5,(Cχ-C 4 -alkoxy) carbonyl for: COOCH 3 , COOC 2 H 5 , COOCH 2 -CH 5 ,
1-Methylethoxycarbonyl, n-Butoxycarbonyl, 1-Methylpropoxy- carbonyl, 2-Methylpropoxycarbonyl oder COOC(CH )3, insbesondere für COOCH3, COOC2H5, COOCH(CH3)2 oder Isobutoxy- carbonyl ;1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or COOC (CH) 3 , in particular for COOCH 3 , COOC 2 H 5 , COOCH (CH 3 ) 2 or isobutoxycarbonyl;
(Cχ-C6-Alkoxy) carbonyl-Cχ-C6-alkoxy für: durch (Cχ-C6-Alkoxy) - carbonyl wie vorstehend genannt substituiertes Cχ-Cg-Alkoxy, also z.B. für Methoxycarbonyl-methoxy, Ethoxycarbonyl- methoxy, n-Propoxycarbonyl-methoxy, n-Butoxycarbonyl-methoxy, 1- (Methoxycarbonyl) ethoxy, 2- (Methoxycarbonyl) ethoxy, 2- (Ethoxycarbonyl) ethoxy, 2- (n-Propoxycarbonyl) ethoxy, 2- (n-Butoxycarbonyl) ethoxy, 3- (Methoxycarbonyl) ropoxy, 3- (Ethoxycarbonyl) propoxy, 3- (n-Propoxycarbonyl) propoxy, 3- (n-Butoxycarbonyl) propoxy, 4- (Methoxycarbonyl) butoxy, 4- (Ethoxycarbonyl) butoxy, 4- (n-Propoxycarbonyl) butoxy, 4- (n-Butoxycarbonyl) butoxy, 5- (Methoxycarbonyl) pentoxy, 5- (Ethoxycarbonyl) entoxy, 5- (n-Propoxycarbonyl) pentoxy, 5- (n-Butoxycarbonyl) butoxy, 6- (Methoxycarbonyl) exoxy, 6- (Ethoxycarbonyl) hexoxy, 6- (n-Propoxycarbonyl) exoxy oder 6- (n-Butoxycarbonyl) hexoxy, insbesondere für Methoxycarbonyl- methoxy oder 1- (Methoxycarbonyl) ethoxy;(Cχ-C 6 -alkoxy) carbonyl-Cχ-C 6 -alkoxy for: C (-Cg-alkoxy substituted by (Cχ-C 6 -alkoxy) carbonyl as mentioned above, for example for methoxycarbonyl-methoxy, ethoxycarbonyl-methoxy, n-propoxycarbonyl-methoxy, n-butoxycarbonyl-methoxy, 1- (methoxycarbonyl) ethoxy, 2- (methoxycarbonyl) ethoxy, 2- (ethoxycarbonyl) ethoxy, 2- (n-propoxycarbonyl) ethoxy, 2- (n-butoxycarbonyl) ethoxy , 3- (methoxycarbonyl) ropoxy, 3- (ethoxycarbonyl) propoxy, 3- (n-propoxycarbonyl) propoxy, 3- (n-butoxycarbonyl) propoxy, 4- (methoxycarbonyl) butoxy, 4- (ethoxycarbonyl) butoxy, 4- ( n-propoxycarbonyl) butoxy, 4- (n-butoxycarbonyl) butoxy, 5- (methoxycarbonyl) pentoxy, 5- (ethoxycarbonyl) entoxy, 5- (n-propoxycarbonyl) pentoxy, 5- (n-butoxycarbonyl) butoxy, 6- ( Methoxycarbonyl) exoxy, 6- (ethoxycarbonyl) hexoxy, 6- (n-propoxycarbonyl) exoxy or 6- (n-butoxycarbonyl) hexoxy, in particular for methoxycarbonyl-methoxy or 1- (methoxycarbonyl) ethoxy;
(Cχ-C6-Alkoxy) carbonyl-Cχ-C6-alkyl für: durch (Cχ-C6-Alkoxy) - carbony^ wie vorstehend genannt substituiertes Cχ-Cg-Alkyl, also z.B. für Methoxycarbonyl-methyl, Ethoxycarbonyl-methyl, n-Propoxycarbonyl-methyl, n-Butoxycarbonyl-methyl , 1- (Methoxycarbonyl) ethyl , 2- (Methoxycarbonyl) ethyl, 2- (Ethoxycarbonyl) ethyl, 2- (n-Propoxycarbonyl) ethyl, 2- (n-Butoxycarbonyl) ethyl, 3- (Methoxycarbonyl) propyl, 3- (Ethoxycarbonyl) pro - pyl, 3- (n-Propoxycarbonyl) propyl, 3- (n-Butoxycarbonyl) propyl, 4- (Methoxycarbonyl) butyl, 4- (Ethoxycarbonyl) butyl , 4- (n-Propoxycarbonyl) butyl , 4- (n-Butoxycarbonyl) butyl, 5- (Methoxycarbonyl) pentyl , 5- (Ethoxycarbonyl) pentyl , 5- (n-Propoxycarbo- nyDpentyl, 5- (n-Butoxycarbonyl) butyl, 6- (Methoxycarbonyl) he- xyl, 6- (Ethoxycarbonyl) hexyl, 6- (n-Propoxycarbonyl) hexyl oder 6- (n-Butoxycarbonyl) hexyl, insbesondere für Methoxycarbonyl- methyl oder 1 - (Methoxycarbonyl) ethyl ; (C3-C6-Alkenyloxy) carbonyl für: Prop-1-en-l-yloxycarbonyl, Prop-2-en-l-yloxycarbonyl, 1-Methylethenyloxycarbonyl, n-Bu- ten-1-yloxycarbonyl, n-Buten-2-yloxycarbonyl , n-Buten-3-yl - oxycarbonyl, 1-Methyl-prop-l-en-l-yloxycarbonyl , 2-Methyl- prop-1-en-l-yloxycarbonyl, 1-Methyl-prop-2-en-l-yloxycar- bonyl, 2-Methyl-prop-2-en-l-yloxycarbonyl, n-Penten-1-yloxy- carbonyl, n-Penten-2-yloxycarbonyl , n-Penten-3-yloxycarbonyl, n-Penten-4-yloxycarbonyl , 1-Methyl-but-l-en-l-yloxycarbonyl , 2-Methyl-but-l-en-l-yloxycarbonyl , 3-Methyl-but-l-en-l-yloxy- carbonyl, l-Methyl-but-2-en-l-yloxycarbonyl, 2-Methyl- but-2-en-l-yloxycarbonyl, 3-Methyl-but-2-en-l-yloxycarbonyl, l-Methyl-but-3-en-l-yloxycarbonyl , 2-Methyl-but-3-en-l-yloxy- carbonyl, 3-Methyl-but-3-en-l-yloxycarbonyl, 1, 1-Dimethyl- prop-2-en-l-yloxycarbonyl, 1, 2-Dimethyl-prop-l-en-l-yloxy- carbonyl, 1, 2-Dimethyl-prop-2-en-l-yloxycarbonyl, 1-Ethyl- prop-l-en-2-yloxycarbonyl, l-Ethyl-prop-2-en-l-yloxycarbonyl, n-Hex-1-en-l-yloxycarbonyl , n-Hex-2-en-l-yloxycarbonyl , n-Hex-3-en-l-yloxycarbonyl , n-Hex-4-en-l-yloxycarbonyl , n-Hex-5-en-l-yloxycarbonyl, 1-Methyl-pent-l-en-l-yloxycar- bonyl, 2-Methyl-pent-l-en-l-yloxycarbonyl, 3-Methyl-pent-l- en-1-yloxycarbonyl, 4-Methyl-pent-l-en-l-yloxycarbonyl, l-Methyl-pent-2-en-l-yloxycarbonyl, 2-Methyl-pent-2-en-l-yl- oxycarbonyl, 3-Methyl-pent-2-en-l-yloxycarbonyl, 4-Methyl- pent-2-en-l-yloxycarbonyl, l-Methyl-pent-3-en-l-yloxycar- bonyl, 2-Methyl-pent-3-en-l-yloxycarbonyl, 3-Methyl-pent-3- en-1-yloxycarbonyl, 4-Methyl-pent-3-en-l-yloxycarbonyl , l-Methyl-pent-4-en-l-yloxycarbonyl, 2-Methyl-pent-4-en-l-yl - oxycarbonyl, 3-Methyl-pent-4-en-l-yloxycarbonyl, 4-Methyl- pent-4-en-l-yloxycarbonyl, 1, l-Dimethyl-but-2-en-l-yloxycar- bonyl, 1 , l-Dimethyl-but-3-en-l-yloxycarbonyl , 1 , 2-Dimethyl- but-1-en-l-yloxycarbonyl , 1, 2-Dimethyl-but-2-en-l-yloxycar- bonyl, 1, 2-Dimethyl-but-3-en-l-yloxycarbonyl , 1, 3-Dimethyl- but-1-en-l-yloxycarbonyl, 1, 3-Dimethyl-but-2-en-l-yloxycar- bonyl, l,-^-Dimethyl-but-3-en-l-yloxycarbonyl , 2 , 2-Dimethyl- but-3-en-l-yloxycarbonyl, 2 , 3-Dimethyl-but-l-en-l-yloxycar- bonyl, 2, 3-Dimethyl-but-2-en-l-yloxycarbonyl, 2 , 3-Dimethyl- but-3-en-l-yloxycarbonyl, 3 , 3-Dimethyl-but-l-en-l-yloxycar- bonyl, 3 , 3-Dimethyl-but-2-en-l-yloxycarbonyl , 1-Ethyl-but-l- en-1-yloxycarbonyl , l-Ethyl-but-2-en-l-yloxycarbonyl , l-Ethyl-but-3-en-l-yloxycarbonyl, 2-Ethyl-but-l-en-l-yloxy- carbonyl, 2-Ethyl-but-2-en-l-yloxycarbonyl, 2-Ethyl-but-3- en-1-yloxycarbonyl, 1,1, 2-Trimethyl-prop-2-en-l-yloxycar- bonyl, l-Ethyl-l-methyl-prop-2-en-l-yloxycarbonyl, 1-Ethyl- 2-methyl-prop-l-en-l-yl-oxycarbonyl oder l-Ethyl-2-methyl- prop-2-en-l-yloxycarbonyl, insbesondere für Prop-2 -en-1 -yl - oxycarbonyl ; (C3-C6-Alkenyloxy) carbonyl-Cχ-C6-alkyl für: Cχ-C6-Alkyl (wie vorstehend definiert) , substituiert mit C -C6-Alkenyloxycarbo- nyl, wie vorstehend definiert;(Cχ-C 6 -alkoxy) carbonyl-Cχ-C 6 -alkyl for: C (-Cg-alkyl substituted by (C --C 6 -alkoxy) - carbony ^ as mentioned above, for example for methoxycarbonyl-methyl, ethoxycarbonyl-methyl , n-propoxycarbonyl-methyl, n-butoxycarbonyl-methyl, 1- (methoxycarbonyl) ethyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 2- (n-propoxycarbonyl) ethyl, 2- (n-butoxycarbonyl) ethyl, 3- (methoxycarbonyl) propyl, 3- (ethoxycarbonyl) propyl, 3- (n-propoxycarbonyl) propyl, 3- (n-butoxycarbonyl) propyl, 4- (methoxycarbonyl) butyl, 4- (ethoxycarbonyl) butyl, 4- (n-propoxycarbonyl) butyl, 4- (n-butoxycarbonyl) butyl, 5- (methoxycarbonyl) pentyl, 5- (ethoxycarbonyl) pentyl, 5- (n-propoxycarbonyldpentyl, 5- (n-butoxycarbonyl) butyl, 6- (methoxycarbonyl) hexyl, 6- (ethoxycarbonyl) hexyl, 6- (n-propoxycarbonyl) hexyl or 6- (n-butoxycarbonyl) hexyl, especially for methoxycarbonylmethyl or 1 - (methoxycarbonyl) ethyl; (C 3 -C 6 alkenyloxy) carbonyl for: prop-1-en-l-yloxycarbonyl, prop-2-en-l-yloxycarbonyl, 1-methylethenyloxycarbonyl, n-buten-1-yloxycarbonyl, n-butene- 2-yloxycarbonyl, n-buten-3-yl-oxycarbonyl, 1-methyl-prop-l-en-l-yloxycarbonyl, 2-methyl-prop-1-en-l-yloxycarbonyl, 1-methyl-prop-2- en-l-yloxycarbonyl, 2-methyl-prop-2-en-l-yloxycarbonyl, n-penten-1-yloxycarbonyl, n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl, n- Penten-4-yloxycarbonyl, 1-methyl-but-l-en-l-yloxycarbonyl, 2-methyl-but-l-en-l-yloxycarbonyl, 3-methyl-but-l-en-l-yloxycarbonyl, l-methyl-but-2-en-l-yloxycarbonyl, 2-methyl-but-2-en-l-yloxycarbonyl, 3-methyl-but-2-en-l-yloxycarbonyl, l-methyl-but-3- en-l-yloxycarbonyl, 2-methyl-but-3-en-l-yloxycarbonyl, 3-methyl-but-3-en-l-yloxycarbonyl, 1, 1-dimethylprop-2-en-l- yloxycarbonyl, 1, 2-dimethyl-prop-l-en-l-yloxycarbonyl, 1, 2-dimethyl-prop-2-en-l-yloxycarbonyl, 1-ethyl-prop-l-en-2-yloxycarbonyl, l-ethyl-prop-2-en-l-yloxycarbonyl, n-hex-1-en-l-yloxycarbo nyl, n-hex-2-en-l-yloxycarbonyl, n-hex-3-en-l-yloxycarbonyl, n-hex-4-en-l-yloxycarbonyl, n-hex-5-en-l-yloxycarbonyl, 1-methyl-pent-l-en-l-yloxycarbonyl, 2-methyl-pent-l-en-l-yloxycarbonyl, 3-methyl-pent-l-en-1-yloxycarbonyl, 4-methyl-pent- l-en-l-yloxycarbonyl, l-methyl-pent-2-en-l-yloxycarbonyl, 2-methyl-pent-2-en-l-yl-oxycarbonyl, 3-methyl-pent-2-en-l- yloxycarbonyl, 4-methyl-pent-2-en-l-yloxycarbonyl, l-methyl-pent-3-en-l-yloxycarbonyl, 2-methyl-pent-3-en-l-yloxycarbonyl, 3-methyl- pent-3-en-1-yloxycarbonyl, 4-methyl-pent-3-en-l-yloxycarbonyl, l-methyl-pent-4-en-l-yloxycarbonyl, 2-methyl-pent-4-en-l- yl - oxycarbonyl, 3-methyl-pent-4-en-l-yloxycarbonyl, 4-methyl-pent-4-en-l-yloxycarbonyl, 1, l-dimethyl-but-2-en-l-yloxycarbonyl, 1, l-dimethyl-but-3-en-l-yloxycarbonyl, 1, 2-dimethyl-but-1-en-l-yloxycarbonyl, 1, 2-dimethyl-but-2-en-l-yloxycarbonyl, 1,2-dimethyl-but-3-en-l-yloxycarbonyl, 1,3-dimethyl-but-1-en-l-yloxycarbonyl, 1,3-dimethyl-but-2-en-l-yloxycarbonyl yl, l, - ^ - dimethyl-but-3-en-l-yloxycarbonyl, 2, 2-dimethyl-but-3-en-l-yloxycarbonyl, 2, 3-dimethyl-but-l-en-l-yloxycar bonyl, 2,3-dimethyl-but-2-en-l-yloxycarbonyl, 2,3-dimethyl-but-3-en-l-yloxycarbonyl, 3,3-dimethyl-but-l-en-l-yloxycar bonyl, 3,3-dimethyl-but-2-en-1-yloxycarbonyl, 1-ethyl-but-1-en-1-yloxycarbonyl, 1-ethyl-but-2-en-1-yloxycarbonyl, 1-ethyl -but-3-en-l-yloxycarbonyl, 2-ethyl-but-l-en-l-yloxycarbonyl, 2-ethyl-but-2-en-l-yloxycarbonyl, 2-ethyl-but-3-ene -1-yloxycarbonyl, 1,1, 2-trimethyl-prop-2-en-l-yloxycarbonyl, l-ethyl-l-methyl-prop-2-en-l-yloxycarbonyl, 1-ethyl-2-methyl -prop-l-en-l-yl-oxycarbonyl or l-ethyl-2-methyl-prop-2-en-l-yloxycarbonyl, especially for prop-2-en-1-yl-oxycarbonyl; (C 3 -C 6 alkenyloxy) carbonyl-Cχ-C 6 -alkyl for: Cχ-C 6 -alkyl (as defined above) substituted with C -C 6 -alkenyloxycarbonyl as defined above;
- C3-Ce-Alkinyloxycarbonyl für: Prop-1-in-l-yloxycarbonyl ,C 3 -Ce alkynyloxycarbonyl for: prop-1-yloxycarbonyl,
Prop-2-in-l-yl, n-But-1-in-l-yloxycarbonyl, n-But-l-in-3-yl - oxycarbonyl, n-But-l-in-4-yloxycarbonyl, n-But-2-in-l-yloxy- carbonyl, n-Pent-1-in-l-yloxycarbonyl, n-Pent-l-in-3-yloxy- carbonyl, n-Pent-l-in-4-yloxycarbonyl, n-Pent-l-in-5-yloxy- carbonyl, n-Pent-2-in-l-yloxycarbonyl , n-Pent-2-in-4-yloxy- carbonyl, n-Pent-2-in-5-yloxycarbonyl , 3-Methyl-but-l-in-3- yloxycarbonyl, 3-Methyl-but-l-in-4-yloxycarbonyl, n-Hex-1-in- 1-yloxycarbonyl, n-Hex-l-in-3-yloxycarbonyl , n-Hex-l-in-4-yl - oxycarbonyl, n-Hex-l-in-5-yloxycarbonyl, n-Hex-l-in-6-yloxy- carbonyl, n-Hex-2-in-l-yloxycarbonyl, n-Hex-2-in-4-yloxycar- bonyl, n-Hex-2-in-5-yloxycarbonyl, n-Hex-2-in-6-yloxycar- bonyl , n-Hex-3-in-l-yloxycarbonyl, n-Hex-3-in-2-yloxycar- bonyl, 3-Methyl-pent-l-in-l-yloxycarbonyl, 3-Methyl-pent-l- in-3-yloxycarbonyl, 3-Methyl-pent-l-in-4-yloxycarbonyl , 3-Methyl-pent-l-in-5-yloxycarbonyl, 4-Methyl-pent-l-in-l-yl- oxycarbonyl, 4-Methyl-pent-2-in-4-yloxycarbonyl oder 4-Methyl-pent-2-in-5-yloxycarbonyl, insbesondere für Prop-2-in-1-yloxycarbonyl;Prop-2-in-l-yl, n-but-1-in-l-yloxycarbonyl, n-but-l-in-3-yl-oxycarbonyl, n-but-l-in-4-yloxycarbonyl, n- But-2-in-1-yloxycarbonyl, n-pent-1-in-1-yloxycarbonyl, n-pent-1-in-3-yloxycarbonyl, n-pent-1-in-4-yloxycarbonyl, n-pent-l-in-5-yloxycarbonyl, n-pent-2-in-l-yloxycarbonyl, n-pent-2-in-4-yloxycarbonyl, n-pent-2-in-5- yloxycarbonyl, 3-methyl-but-l-in-3-yloxycarbonyl, 3-methyl-but-l-in-4-yloxycarbonyl, n-hex-1-in- 1-yloxycarbonyl, n-hex-l-in 3-yloxycarbonyl, n-hex-l-in-4-yl - oxycarbonyl, n-hex-l-in-5-yloxycarbonyl, n-hex-l-in-6-yloxycarbonyl, n-hex-2- in-1-yloxycarbonyl, n-hex-2-in-4-yloxycarbonyl, n-hex-2-in-5-yloxycarbonyl, n-hex-2-in-6-yloxycarbonyl, n-hex 3-in-1-yloxycarbonyl, n-hex-3-in-2-yloxycarbonyl, 3-methyl-pent-1-in-1-yloxycarbonyl, 3-methyl-pent-1-in-3-yloxycarbonyl, 3-methyl-pent-l-in-4-yloxycarbonyl, 3-methyl-pent-l-in-5-yloxycarbonyl, 4-methyl-pent-l-in-l-yl-oxycarbonyl, 4-methyl-pent- 2-in-4-yloxycarbonyl or 4-methyl-pent-2-in-5-yloxycarbonyl, ins especially for prop-2-in-1-yloxycarbonyl;
- (C3-C6-Alkinyloxy) carbonyl-Cχ-C4-alkyl für: Cχ-C4-Alkyl (wie vorstehend definiert) substituiert durch C3-C6-Alkinyloxy- carbonyl, wie vorstehend definiert;- (C 3 -C 6 alkynyloxy) carbonyl-Cχ-C 4 -alkyl for: Cχ-C 4 -alkyl (as defined above) substituted by C 3 -C 6 -alkynyloxycarbonyl as defined above;
Cχ-C5-Alkoxy- (Cχ-C6-alkoxy) carbonyl-C -C6-alkyl für: (Cχ-Cg-Alkoxy) carbonyl-Cχ-Cs-alkyl wie vorstehend definiert, substituiert durch Cχ-C6-Alkoxy, wie vorstehend definiert;Cχ-C 5 -alkoxy- (Cχ-C 6 -alkoxy) carbonyl-C -C 6 -alkyl for: (Cχ-Cg-alkoxy) carbonyl-Cχ-Cs-alkyl as defined above, substituted by Cχ-C 6 - Alkoxy as defined above;
Cχ-C4-Halogenalkoxycarbonyl für: einen Cχ-C4-Alkoxyrest wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, also z.B. Chlormethoxycarbonyl, Dichlormethoxycarbonyl, Trichlormeth- oxycarbonyl, Fluormethoxycarbonyl, Difluormethoxycarbonyl , Trifluormethoxycarbonyl, Chlorfluormethoxycarbonyl, Dichlor- fluormethoxycarbonyl, Chlordifluormethoxycarbonyl , 2-Fluor- ethoxycarbonyl, 2-Chlorethoxycarbonyl, 2-Bromethoxycarbonyl, 2-Iodethoxycarbonyl, 2 , 2-Difluorethoxycarbonyl , 2,2,2-Tri- fluorethoxycarbonyl, 2-Chlor-2-fluorethoxycarbonyl , 2-Chlor- 2 , 2-difluorethoxycarbonyl , 2 , 2-Dichlor-2-fluorethoxycarbonyl , 2,2, 2-Trichlorethoxycarbonyl , Pentafluorethoxycarbonyl , 2-Fluorpropoxycarbonyl, 3-Fluorpropoxycarbonyl, 2,2-Difluor- propoxycarbonyl, 2 , 3-Difluorpropoxycarbonyl , 2-Chlorpropoxy- carbonyl, 3-Chlorpropoxycarbonyl , 2 , 3-Dichlorprσpoxycarbonyl , 2-Brompropoxycarbonyl, 3-Brompropoxycarbonyl , 3 , 3 , 3-Trifluor- propoxycarbonyl , 3,3, 3-Trichlorpropoxycarbonyl, 2,2,3,3, 3-Pentafluorpropoxycarbonyl, Heptafluorpropoxycar- bonyl, 1- (Fluormethyl) -2-fluorethoxycarbonyl, 1- (Chlor- methyl) -2-chlorethoxycarbonyl, 1- (Brommethyl) -2-bromethoxy- carbonyl, 4-Fluorbutoxycarbonyl, 4-Chlorbutoxycarbonyl , 4-Brombutoxycarbonyl oder Nonafluorbutoxycarbonyl, insbesondere für 2 -Chlorethoxycarbonyl oder 2 , 2 , 2 -Trifluorethoxycarbonyl ;Cχ-C 4 haloalkoxycarbonyl for: a Cχ-C 4 alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethoxycarbonyl, dichloromethoxycarbonyl, trichloromethoxycarbonyl, fluoromethoxycarbonyl, difluoromethoxycarbonyl, Trifluoromethoxycarbonyl, chlorofluoromethoxycarbonyl, dichlorofluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2, 2-difluoroethoxycarbonyl, 2,2,2-tri-fluoroethoxycarbonyl, 2 fluoroethoxycarbonyl, 2-chloro-2, 2-difluoroethoxycarbonyl, 2, 2-dichloro-2-fluoroethoxycarbonyl, 2,2, 2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2,2-difluoropropoxycarbonyl, 2, 3-difluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2, 3-dichloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 3, 3, 3-trifluoropropoxycarbonyl, 3,3, 3-trichloropropoxycarbonyl, 2,2,3,3, 3-pentafluoropropoxycarbonyl, heptafluoropropoxycarbonyl, 1- (fluoromethyl) -2- fluoroethoxycarbonyl, 1- (chloromethyl) -2-chloroethoxycarbonyl, 1- (bromomethyl) -2-bromethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl or nonafluorobutoxycarbonyl, especially for 2-chloroethoxycarbonyl or 2, 2, 2 -trifluoroethoxycarbonyl;
(Cχ-C4-Halogenalkoxy) carbonyl-Cχ-C4-alkyl für: Cχ-C4-Alkyl (wie vorstehend definiert, substituiert durch Cχ-C4-Halogen- alkoxycarbonyl wie vorstehend definiert;(Cχ-C 4 haloalkoxy) carbonyl-Cχ-C 4 alkyl for: Cχ-C 4 alkyl (as defined above, substituted by Cχ-C 4 haloalkoxycarbonyl as defined above;
C -C6-Cycloalkoxycarbonyl für: Cyclopropyloxycarbonyl, Cyclo- butyloxycarbonyl, Cyclopentyloxycarbonyl oder Cyclohexyloxycarbonyl ;C -C 6 cycloalkoxycarbonyl for: cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl or cyclohexyloxycarbonyl;
(C3-C6-Cycloalkoxy) carbonyl-Cχ-C4-alkyl für: C -C -Alkyl (wie vorstehend definiert) substituiert durch C3-Cg-Cycloalkyloxy- carbonyl wie vorstehend definiert;(C 3 -C6-Cycloalkoxy) carbonyl-Cχ-C 4 -alkyl for: C -C -alkyl (as defined above) substituted by C 3 -Cg-cycloalkyloxycarbonyl as defined above;
(Cχ-C6-Alkoxy) carbonyl- (Cχ-C6-alkoxy) carbonyl-Cχ-C6-alkyl für: (Cχ-Cg-Alkoxy) carbonyl-Cχ-Cg-alkyl (wie vorstehend definiert) substituiert durch Cχ-Cg-Alkoxycarbonyl, wie vorstehend definiert;(Cχ-C 6 -alkoxy) carbonyl- (Cχ-C 6 -alkoxy) carbonyl-Cχ-C 6 -alkyl for: (Cχ-Cg-alkoxy) carbonyl-Cχ-Cg-alkyl (as defined above) substituted by Cχ -Cg alkoxycarbonyl as defined above;
(C3-C6-Alkenyloxy) carbonyl- (Cχ-C6-alkoxy) carbonyl-Cχ-C6-alkyl für: (Cχ-C6-Alkoxy) carbonyl-Cχ-C6-alkyl (wie vorstehend definiert) , substituiert durch C3-C6-Alkenyloxycarbonyl (wie vorstehend definiert) ;(C 3 -C 6 alkenyloxy) carbonyl- (Cχ-C 6 -alkoxy) carbonyl-Cχ-C 6 -alkyl for: (Cχ-C 6 -alkoxy) carbonyl-Cχ-C 6 -alkyl (as defined above) substituted by C 3 -C 6 alkenyloxycarbonyl (as defined above);
(C3-C6-Alkinyloxy) carbonyl) - (Cχ-C6-alkoxy) carbonyl-Cχ-Cg-alkyl für: (C -^Cß" lkoxy) carbonyl-Cχ-Cg-alkyl (wie vorstehend definiert) , substituiert durch C3-C6-Alkinyloxycarbonyl (wie vorstehend definiert) ;(C 3 -C 6 alkynyloxy) carbonyl) - (Cχ-C 6 -alkoxy) carbonyl-Cχ-Cg-alkyl for: (C - ^ C ß "lkoxy) carbonyl-Cχ-Cg-alkyl (as defined above) substituted with C 3 -C 6 alkynyloxycarbonyl (as defined above);
Carboxyl- (Cχ-C6-alkoxy) carbonyl-Cχ-C6-alkyl für: (Cχ-Cg-Alk- oxy) carbonyl-Cχ-Cg-alkyl (wie vorstehend definiert), substi- tuiert durch eine Cyrboxylgruppe;Carboxyl (Cχ-C6-alkoxy) carbonyl-Cχ-C 6 -alkyl for: (Cχ-Cg-alkoxy) carbonyl-Cχ-Cg-alkyl (as defined above) substituted by a Cyrboxyl group;
Phenoxycarbonyl-Cχ-Cg-alkyl für: Cχ-Cg-alkyl wie vorstehend definiert, substituiert durch Phenoxycarbonyl ; Phenyl- (Cχ-Cg- alkoxy) carbonyl für: z.B. Benzyloxycarbonyl , 1-Phenylethoxycarbonyl, 2-Phenylethoxycarbonyl , 1-Phenyl- prop-1-oxycarbonyl, 2-Phenylprop-1-oxycarbonyl, 3-Phenyl - prop-1-oxycarbonyl, 1-Phenylbut-l-oxycarbonyl, 2-Phenyl- but-1-oxycarbonyl, 3-Phenylbut-l-oxycarbonyl, 4-Phenyl- but-1-oxycarbonyl, l-Phenylbut-2-oxycarbonyl, 2-Phenyl- but-2-oxycarbonyl, 3-Phenylbut-2-oxycarbonyl , 4-Phenyl- but-2-oxycarbonyl, 1- (Phenylmethyl) -eth-1-oxycarbonyl, 1- (Phenylmethyl) -1- (methyl) -eth-1-oxycarbonyl oder 1- (Phenyl - methyl) -prop-1-oxycarbonyl, insbesondere für Benzyloxycarbonyl oder 2-Phenylethoxycarbonyl;Phenoxycarbonyl-Cχ-Cg-alkyl for: Cχ-Cg-alkyl as defined above, substituted by phenoxycarbonyl; Phenyl- (Cχ-Cg-alkoxy) carbonyl for: e.g. benzyloxycarbonyl, 1-phenylethoxycarbonyl, 2-phenylethoxycarbonyl, 1-phenyl-prop-1-oxycarbonyl, 2-phenylprop-1-oxycarbonyl, 3-phenyl-prop-1-oxycarbonyl , 1-phenylbut-1-oxycarbonyl, 2-phenylbut-1-oxycarbonyl, 3-phenylbut-1-oxycarbonyl, 4-phenylbut-1-oxycarbonyl, 1-phenylbut-2-oxycarbonyl, 2-phenylbut -2-oxycarbonyl, 3-phenylbut-2-oxycarbonyl, 4-phenylbut-2-oxycarbonyl, 1- (phenylmethyl) -eth-1-oxycarbonyl, 1- (phenylmethyl) -1- (methyl) -eth-1 -oxycarbonyl or 1- (phenylmethyl) prop-1-oxycarbonyl, especially for benzyloxycarbonyl or 2-phenylethoxycarbonyl;
Phenyl- (Cχ-Cg-alkoxy) carbonyl-Cχ-C6-alkyl für: Cχ-C6-Alkyl (wie vorstehend definiert) , substituiert durch Phenyl- (Cχ-Cg-alkoxy) carbonyl, wie vorstehend definiert.Phenyl- (Cχ-Cg-alkoxy) carbonyl-Cχ-C 6 -alkyl for: Cχ-C 6 -alkyl (as defined above) substituted by phenyl- (Cχ-Cg-alkoxy) carbonyl as defined above.
Im Hinblick auf die Verwendung der substituierten Pyridazione I als Herbizide und/oder als desikkant/defoliant wirksame Verbindungen haben die Variablen vorzugsweise folgende Bedeutungen, und zwar jeweils für sich allein oder in Kombination:With regard to the use of the substituted pyridazione I as herbicides and / or as desiccant / defoliant compounds, the variables preferably have the following meanings, individually or in combination:
R1 Wasserstoff, Halogen, Cχ-C6-Alkoxy, Cχ-Cg-Alkylthio, NH2, Cχ-Cg-Alkylamino oder Di- (Cχ-Cg-alkyl) amino;R 1 is hydrogen, halogen, Cχ-C 6 alkoxy, Cχ-Cg-alkylthio, NH 2 , Cχ-Cg-alkylamino or di- (Cχ-Cg-alkyl) amino;
R2 Halogen, Cχ-Cg-Alkyl, C -Cg-Halogenalkyl, Cχ-Cg-Alkylthio, Cχ-Cg-Alkylsulfinyl oder Cχ-Cg-Alkylsulfonyl;R 2 is halogen, Cχ-Cg-alkyl, C -Cg-haloalkyl, Cχ-Cg-alkylthio, Cχ-Cg-alkylsulfinyl or Cχ-Cg-alkylsulfonyl;
R3 Wasserstoff, Hydroxy, Cχ-Cg-Alkyl oder Cχ-Cg-Alkoxy;R 3 is hydrogen, hydroxy, Cχ-Cg-alkyl or Cχ-Cg-alkoxy;
R4-R7 Wasserstoff;R 4 -R 7 hydrogen;
R8 OR8';R 8 OR 8 ';
R8' Wasserstoff, Cχ-C6-Alkyl, C3-C6-Cycloalkyl, Cyano- (Cχ-C6- alkyl) , C3-C6-Alkenyl, C3-C6-Alkinyl, Carboxyl-Cχ-C4-alkyl, (C -C -Alkoxy) carbonyl-Cχ-C4-alkyl, (C -Cg-Alkenyloxy) - carbonyl-Cχ-C4-alkyl, (C3-Cg-Alkinyloxy) carbonyl-Cχ-C4- alkyl , Cχ-C4-Alkoxy- (Cχ-C4-alkoxy) carbonyl-Cχ-C4-alkyl , (Cχ-C4-Alkoxy) carbonyl- (Cχ-C4-alkoxy) carbonyl-Cχ-C4-alkyl , Carboxyl- (Cχ-C4-alkoxy) carbonyl-Cχ-C4-alkyl,R 8 'is hydrogen, Cχ-C 6 alkyl, C 3 -C 6 cycloalkyl, cyano- (Cχ-C 6 alkyl), C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, carboxyl-Cχ -C 4 -alkyl, (C -C -alkoxy) carbonyl-C C-C 4 -alkyl, (C -Cg-alkenyloxy) - carbonyl-Cχ-C 4 -alkyl, (C 3 -Cg-alkynyloxy) carbonyl-Cχ -C 4 - alkyl, Cχ-C 4 -alkoxy- (Cχ-C 4 -alkoxy) carbonyl-Cχ-C 4 -alkyl, (Cχ-C 4 -alkoxy) carbonyl- (Cχ-C 4 -alkoxy) carbonyl- Cχ-C 4 -alkyl, carboxyl- (Cχ-C 4 -alkoxy) carbonyl-Cχ-C 4 -alkyl,
-CH(R9) -C (COOR10) =N-OR14, -CH (R9) -CO-N [CH (R9 ) -COOR10] -OR14, -CH(R9) -C [-OCH(R9) -COOR10] =N-OR14, insbesondere -CH(R9) -C(COOR10)=N-OR14;-CH (R 9 ) -C (COOR 10 ) = N-OR 14 , -CH (R 9 ) -CO-N [CH (R 9 ) -COOR 10 ] -OR 14 , -CH (R 9 ) -C [-OCH (R 9 ) -COOR 10 ] = N-OR 14 , especially -CH (R 9 ) -C (COOR 10 ) = N-OR 14 ;
R9,R10 unabhängig voneinander Wasserstoff oder Cχ-Cg-Alkyl; R11 , R12 unabhängig voneinander Was sers tof f , Cχ-Cg-Alkyl , Carboxyl - Cχ-C4-alkyl , (Cχ-C4-Alkoxy) carbonyl-Cχ-C -alkyl ;R 9 , R 10 independently of one another are hydrogen or Cχ-Cg-alkyl; R 11 , R 12 independently of one another Was sers tof f, Cχ-Cg-alkyl, carboxyl - Cχ-C 4 -alkyl, (Cχ-C 4 -alkoxy) carbonyl-Cχ-C -alkyl;
R14 Cχ-Cg-Alkyl ;R 14 Cχ-Cg-alkyl;
R20 Halogen, insbesondere Chlor oder Brom;R 20 halogen, especially chlorine or bromine;
R21 Wasserstoff oder Chlor.R 21 is hydrogen or chlorine.
Insbesondere bevorzugt sind auch Verbindungen der Formel I, in denen R1 bis R6 die vorstehend genannte Bedeutung haben, R8 für N0 steht, R20 und R21 unabhängig voneinander für Wasserstoff, CI oder Brom stehen und R7 für Wasserstoff, Carboxyl, (Cχ-Cg-Alkoxy) - carbonyl , (Cχ-Cg-Alkoxy) carbonyl- (Cχ-Cg-alkoxy) carbonyl oder Cχ-Cg-Alkoxy steht.Particular preference is also given to compounds of the formula I in which R 1 to R 6 have the abovementioned meaning, R 8 is N0, R 20 and R 21 independently of one another are hydrogen, CI or bromine and R 7 is hydrogen, carboxyl, (Cχ-Cg-alkoxy) - carbonyl, (Cχ-Cg-alkoxy) carbonyl- (Cχ-Cg-alkoxy) carbonyl or Cχ-Cg-alkoxy.
Weiterhin sind bevorzugt Verbindungen, in denen R1 für Amino, R2 für C -C6-Alkylthio, Cχ-C3-Alkylsulfinyl oder Cχ-C6-Alkylsulfonyl , R3-R7 für Wasserstoff und R8-R21 wie vorstehend definiert sind.Also preferred are compounds in which R 1 for amino, R 2 for C -C 6 alkylthio, Cχ-C 3 alkylsulfinyl or Cχ-C 6 alkylsulfonyl, R 3 -R 7 for hydrogen and R 8 -R 21 such as are defined above.
Als weitere bevorzugte Gruppe von Verbindungen sind solche zu nennen, in denen R1 für Amino R2 für Cχ-Cg-Alkylthio, Cχ-Cg-Alkyl- sulfinyl oder Cχ-C5-Alkylsulfonyl, R3-R6 für Wasserstoff, R7 für Wasserstoff, Carboxyl, (Cχ-Cg-Alkoxy) carbonyl, (Cχ-Cg-Alkoxy) - carbonyl- (Cχ-Cg-alkoxy) carbonyl oder Cχ-Cg-Alkoxy, R8 für N02 und R20 und R21 unabhängig voneinander für Wasserstoff, Chlor oder Brom stehen.A further preferred group of compounds are those in which R 1 for amino R 2 for Cχ-Cg-alkylthio, Cχ-Cg-alkylsulfinyl or Cχ-C 5 -alkylsulfonyl, R 3 -R 6 for hydrogen, R 7 for hydrogen, carboxyl, (Cχ-Cg-alkoxy) carbonyl, (Cχ-Cg-alkoxy) - carbonyl- (Cχ-Cg-alkoxy) carbonyl or Cχ-Cg-alkoxy, R 8 for N0 2 and R 20 and R 21 independently of one another represent hydrogen, chlorine or bromine.
Ganz besonders bevorzugt sind die in der nachfolgenden Tabelle 1 aufgeführten Verbindungen der Formel Ia:The compounds of the formula Ia listed in Table 1 below are very particularly preferred:
Figure imgf000019_0001
Figure imgf000019_0001
Tabelle 1Table 1
Figure imgf000019_0002
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000019_0002
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
99/18082
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
99/18082
3030
Figure imgf000032_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Besonders bevorzugt sind weiterhin substituierte Benz(o)yl- pyridazinone der Formel Ib (Verbindungen 2.1-2.336) die sich von den Verbindungen 1.1 bis 1.336 lediglich dadurch unterscheiden, daß R2 für H3C(0)S anstelle von H3C(02)S steht:
Figure imgf000033_0001
Figure imgf000034_0001
Substituted benz (o) yl-pyridazinones of the formula Ib (compounds 2.1-2.336) which differ from the compounds 1.1 to 1.336 only in that R 2 for H 3 C (0) S instead of H 3 C ( 0 2 ) S stands:
Figure imgf000035_0001
Figure imgf000035_0001
Ebenfalls besonders bevorzugt sind Verbindungen der Formel Ic (Verbindungen 3.1 bis 3.336), die sich von den Verbindungen 1.1-1.336 lediglich dadurch unterscheiden, daß R2 für H3CS anstelle von H3C(02)S steht:Also particularly preferred are compounds of the formula Ic (compounds 3.1 to 3,336) which differ from the compounds 1.1-1.336 only in that R 2 is H 3 CS instead of H 3 C (0 2 ) S:
Figure imgf000035_0002
Figure imgf000035_0002
Ferner sind bevorzugt Verbindungen der Formel Id gemäß Tabelle 4:Compounds of the formula Id according to Table 4 are also preferred:
Tabelle 4Table 4
Id {R3,R4,R ,R6 = H; R8 = N02)Id {R 3 , R 4 , R, R 6 = H; R 8 = N0 2 )
Figure imgf000035_0003
Figure imgf000035_0003
Figure imgf000035_0004
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000038_0001
Die erfindungsgemäßen substituierten Pyridazinone der Formel I sind auf verschiedene Weise erhältlich, insbesondere nach einem der folgenden Verfahren:
Figure imgf000035_0004
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000038_0001
The substituted pyridazinones of the formula I according to the invention can be obtained in various ways, in particular by one of the following processes:
Verfahren A)Procedure A)
Umsetzung von substituierten Pyridazinonen der Formel II mit substituierten Benzylhalogeniden bzw. Benzylmesylaten der Formel lila bzw. Illb in Gegenwart einer Base:Reaction of substituted pyridazinones of the formula II with substituted benzyl halides or benzyl mesylates of the formula lilac or Illb in the presence of a base:
Figure imgf000039_0001
Figure imgf000039_0001
( II ) (lila: X = Hai) (Illb: X = OS02CH3)(II) (purple: X = shark) (Illb: X = OS0 2 CH 3 )
Figure imgf000039_0002
Figure imgf000039_0002
Reaktionen dieser Art sind allgemein bekannt, beispielsweise aus der folgenden Literatur:Reactions of this type are generally known, for example from the following literature:
K. Dury, Angew. Chem. 7_7, 282 (1965) ; K. Kaji et al . , Chem. Parm. Bull. 18., 147 (1970);K. Dury, Angew. Chem. 7_7, 282 (1965); K. Kaji et al. , Chem. Parm. Bull. 18., 147 (1970);
K. Kaji und M. Kuzuja, Chem. Pharm. Bull. 18, 970 (1970);K. Kaji and M. Kuzuja, Chem. Pharm. Bull. 18, 970 (1970);
V. Konecny et al . , coll. Czech. Chem. Commun. 50, 492 (1985).V. Konecny et al. , coll. Czech. Chem. Commun. 50, 492 (1985).
Üblicherweise«, arbeitet man in einem inerten Lösungs- oder Ver- dünnungsmittel, insbesondere in einem dipolar aprotischenUsually «, one works in an inert solvent or diluent, especially in a dipolar aprotic
Lösungsmittel wie z.B. N,N-Dimethylformamid, N-Methylpyrrolidon, Tetrahydrofuran, Dioxan, 1 , 2 -Diethoxyethan, tert . -Butylmethyl - ether, Diethylether usw.Solvents such as e.g. N, N-dimethylformamide, N-methylpyrrolidone, tetrahydrofuran, dioxane, 1, 2 -diethoxyethane, tert. -Butylmethyl - ether, diethyl ether etc.
Als Basen kommen z.B. Alkalimetallcarbonate wie Natriumcarbonat, Alkalimetallhydrogencarbonate wie Natriumhydrogencarbonat und -hydroxyde wie Natriumhydroxid in Betracht. Auch Stickstoffbasen wie Triethylamin, Dicyclohexylethylamin, Pyridin und 4-Dimethyl- aminopyridin können verwendet werden. Die Reaktionstemperatur liegt üblicherweise im Bereich von 0 bis 100°C.Suitable bases are, for example, alkali metal carbonates such as sodium carbonate, alkali metal bicarbonates such as sodium bicarbonate and hydroxides such as sodium hydroxide. Nitrogen bases such as triethylamine, dicyclohexylethylamine, pyridine and 4-dimethylaminopyridine can also be used. The reaction temperature is usually in the range from 0 to 100.degree.
Üblicherweise werden die Komponenten in etwa stöchiometrischen Mengen eingesetzt, jedoch kann ein Überschuß einer der Komponenten, z.B. im Hinblick auf eine möglichst vollständige Umsetzung der anderen Komponente, vorteilhaft sein.The components are usually used in approximately stoichiometric amounts, but an excess of one of the components, e.g. with a view to implementing the other component as completely as possible.
Die Pyridazinone der Formel II sind teilweise käuflich, teilweise literaturbekannt bzw. nach literaturbekannten Methoden leicht herstellbar.Some of the pyridazinones of the formula II are commercially available, some are known from the literature or can be easily prepared by methods known from the literature.
Die Benzylhalogenide der Formel III sind teilweise literaturbekannt oder sind nach Literaturbekannten Methoden leicht herstell - bar. So wird z.B. in der älteren Anmeldung DE-A 197 11 569.1 die Darstellung von 2 , 3 -Dichlor-4 -methoxybenzylbromid durch Brom- methylierung von 2 , 3 -Dichloranisol beschrieben.Some of the benzyl halides of the formula III are known from the literature or can easily be prepared by methods known from the literature. For example, in the earlier application DE-A 197 11 569.1 describes the preparation of 2,3-dichloro-4-methoxybenzyl bromide by bromomethylation of 2,3-dichloroanisole.
Verfahren B) Acylierung von Pyridazinonen der Formel II mit einem substituierten Benzoesäurechlorid der Formel IV in Gegenwart einer Base:Process B) Acylation of pyridazinones of the formula II with a substituted benzoic acid chloride of the formula IV in the presence of a base:
Figure imgf000040_0001
Figure imgf000040_0001
Base •HC1Base • HC1
Reaktionen dieser Art sind bekannt, z.B. aus: M.L. Carmellino, Farmaco 48., 1427 (1993).Such reactions are known, e.g. from: M.L. Carmellino, Farmaco 48, 1427 (1993).
Üblicherweise arbeitet man in einem inerten Lösungs- oder Verdün- nungsmittel, z.B. in Toluol oder Dichlormethan. Gegebenenfalls kann auch die eingesetzte Base als Lösungsmittel dienen, beispielsweise im Falle des Pyridins . Als Basen kommen z.B. Alkalimetallcarbonate, -hydrogencarbonate und -hydroxyde, wie NaC03, NaHC03 und Natriumhydroxid in Betracht. Auch Stickstoffbasen wie Triethylamin, Dicyclohexyl - ethylamin, Pyridin und 4 -Dirnethylaminopyridin können verwendet werden.Usually one works in an inert solvent or diluent, for example in toluene or dichloromethane. Optionally, the base used can also serve as a solvent, for example in the case of pyridine. Suitable bases are, for example, alkali metal carbonates, hydrogen carbonates and hydroxides, such as NaC0 3 , NaHC0 3 and sodium hydroxide. Nitrogen bases such as triethylamine, dicyclohexylethylamine, pyridine and 4-dimethylamino pyridine can also be used.
Die Reaktion kann auch in einem zweiphasigen Gemisch, z.B. Toluol und wäßriger Natronlauge, durchgeführt werden, gegebenenfalls in Gegenwart eines Phasentransferkatalysators .The reaction can also be carried out in a two-phase mixture, e.g. Toluene and aqueous sodium hydroxide solution are carried out, optionally in the presence of a phase transfer catalyst.
Die Benzoesäurechloride der Formel IV sind teilweise literatur- bekannt oder sind nach literaturbekannten Methoden leicht herstellbar.Some of the benzoic acid chlorides of the formula IV are known from the literature or can easily be prepared by methods known from the literature.
Verfahren C>Procedure C>
Umsetzung von substituierten Pyridazinonen der Formel I (R8' = H) mit Alkylhalogeniden der Formel V, bei denen R8' die gleiche Bedeutung hat wie in I, mit der Maßgabe, daß R8' Φ H ist, in Gegenwart einer Base:Reaction of substituted pyridazinones of the formula I (R 8 '= H) with alkyl halides of the formula V in which R 8 ' has the same meaning as in I, with the proviso that R 8 'Φ H, in the presence of a base:
Figure imgf000041_0001
Figure imgf000041_0001
Reaktionen dieser Art sind allgemein bekannt, beispielsweise aus der folgenden Literatur:Reactions of this type are generally known, for example from the following literature:
H. Meerwein in Houben-Weyl, Methoden der Organischen Chemie,H. Meerwein in Houben-Weyl, Methods of Organic Chemistry,
4. Aufl., Band VI/3, Seite 54 ff.;4th edition, Volume VI / 3, page 54 ff .;
H. Förster et al . , DE-A 32 20 524;H. Forster et al. , DE-A 32 20 524;
J. Stetter et al . , DE-A 37 12 987. Üblicherweise arbeitet man in einem inerten Lösungs - oder Verdünnungsmittel, insbesondere einem dipolar aprotischen Lösungsmittel wie z.B. N,N-Dimethylformamid, N-Methylpyrrolidon, Tetrahydrofu- ran, Dioxan, 1, 2 -Diethoxyethan, tert . -Butylmethylether , Diethyl- ether usw.J. Stetter et al. , DE-A 37 12 987. Usually one works in an inert solvent or diluent, especially a dipolar aprotic solvent such as N, N-dimethylformamide, N-methylpyrrolidone, tetrahydrofuran, dioxane, 1, 2-diethoxyethane, tert. -Butyl methyl ether, diethyl ether, etc.
Als Basen kommen z.B. Alkalimetallcarbonate, -hydrogencarbonate und -hydroxyde wie Na2C03, NaHCÜ3 und NaOH in Betracht. Auch Stickstoffbasen, z.B. Triethylamin, Dicyclohexylethylamin, Pyri - din, 4 -Dirnethylaminopyridin, und Alkalimetallalkoholate wie Natriummethylat und Natriumethylat können verwendet werden.Suitable bases are, for example alkali metal carbonates, bicarbonates and hydroxides such as Na 2 C0 3, NaHCÜ 3 and NaOH into consideration. Nitrogen bases, for example triethylamine, dicyclohexylethylamine, pyridine, 4-dimethylamino pyridine, and alkali metal alcoholates such as sodium methylate and sodium ethylate can also be used.
Die Reaktionstemperatur liegt normalerweise bei 0 bis 100°C.The reaction temperature is usually 0 to 100 ° C.
Üblicherweise werden die Komponenten in etwa stöchiometrischen Mengen eingesetzt, jedoch kann ein Überschuß einer der Komponenten, z.B. im Hinblick auf eine möglichst vollständige Umsetzung der anderen Komponente, vorteilhaft sein.The components are usually used in approximately stoichiometric amounts, but an excess of one of the components, e.g. with a view to implementing the other component as completely as possible.
Die Alkylhalogenide der Formel V sind teilweise käuflich, teilweise Literaturbekannt bzw. nach literaturbekannten Methoden leicht darstellbar.Some of the alkyl halides of the formula V are commercially available, some are known from the literature or can easily be prepared by methods known from the literature.
Verfahren D) Die substituierten Benz (o) ylpyridazinone der Formel I, bei denen R1 für Amino oder (Di) alkylamino und R2 für Cχ-Cg-Alkylthio, Cχ-Cg-Alkylsulfinyl oder Cχ-Cg-Alkylsulfonyl steht, lassen sich aus den Benz (o) ylpyridazinonen der Formel I, bei denen R1 und R2 für Chlor stehen, gemäß folgendem Syntheseschema 1 darstellen: Process D) The substituted benz (o) ylpyridazinones of the formula I in which R 1 is amino or (di) alkylamino and R 2 is Cχ-Cg-alkylthio, Cχ-Cg-alkylsulfinyl or Cχ-Cg-alkylsulfonyl can be from the benz (o) ylpyridazinones of the formula I in which R 1 and R 2 are chlorine, according to the following synthesis scheme 1:
Syntheseschema 1:Synthesis scheme 1:
Figure imgf000043_0001
l M = Na, K)
Figure imgf000043_0001
l M = Na, K)
I (R = R2 = CI}I (R = R 2 = CI}
(Oxidation)(Oxidation)
Figure imgf000043_0002
Figure imgf000043_0002
I {R1 = CI, R2 = SR}I {R 1 = CI, R 2 = SR}
Figure imgf000043_0003
Figure imgf000043_0003
{R1 = CI, R2 S(0)n-R, n = 0, 1, 2}{R 1 = CI, R 2 S (0) n -R, n = 0, 1, 2}
Figure imgf000043_0004
Figure imgf000043_0004
{R1 = NR' R" , R2 ={R 1 = NR 'R ", R 2 =
R-S(0)n, n = 0, 1, ■ 2}RS (0) n , n = 0, 1, ■ 2}
Syntheseschritt 1 ist die selektive Substitution des Chlors in der 5-Position eines 4 , 5 -Dichlor- 3 (2H) -pyridazinons durch einen Alkylthiorest. Reaktionen dieser Art sind allgemein bekannt, beispielsweise aus der folgenden Literatur: K. Dury, Angew. Chem. 7_7, 282 (1965);Synthesis step 1 is the selective substitution of the chlorine in the 5-position of a 4, 5-dichloro-3 (2H) -pyridazinone by an alkylthio radical. Reactions of this type are generally known, for example from the following literature: K. Dury, Angew. Chem. 7_7, 282 (1965);
M. Takaya et al., Yakugaku Zasshi £8./ 1530 (1978);M. Takaya et al., Yakugaku Zasshi £ 8/1530 (1978);
J.W. Lyga, J. Het. Chem. 5, 1557 (1988) .J.W. Lyga, J. Het. Chem. 5, 1557 (1988).
5 Um eine möglichst hohe Selektivität zu erreichen, arbeitet man vorzugsweise in einem polaren Lösungsmittel oder Lösungsmittel - gemisch (vergl. J.W. Lyga, 1988) mit hoher Dielektrizitätskonstante, beispielsweise Methanol, Ethanol, N,N-Dimethylformamid, Dimethylsulfoxid, Tetrahydrofuran/Wasser, Pyridin/Wasser, Metha- 10 nol/Wasser.5 In order to achieve the highest possible selectivity, it is preferred to work in a polar solvent or solvent mixture (cf. JW Lyga, 1988) with a high dielectric constant, for example methanol, ethanol, N, N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran / water, pyridine / Water, methanol / water.
Die Reaktionstemperatur liegt normalerweise bei (-10) bis +50°C, vorzugsweise bei 0 bis 30°C.The reaction temperature is normally (-10) to + 50 ° C, preferably 0 to 30 ° C.
15 Zur Erzielung einer möglichst hohen Selektivität werden die beiden Komponenten in etwa stöchiometrischen Mengen eingesetzt, jedoch kann ein geringer Überschuß einer der Komponenten verfahrenstechnische Vorteile bringen.15 To achieve the highest possible selectivity, the two components are used in approximately stoichiometric amounts, but a slight excess of one of the components can bring process engineering advantages.
20 Syntheseschritt 2 ist optional und beinhaltet die Oxidation des Sulfids zum Sulfoxid bzw. Sulfon. Reaktionen dieser Art sind allgemein bekannt, beispielsweise aus der folgenden Literatur:20 Synthesis step 2 is optional and involves the oxidation of the sulfide to the sulfoxide or sulfone. Reactions of this type are generally known, for example from the following literature:
G. Kresze in Houben Weyl , Methoden der Organischen Chemie, Bd. 25 Eil 1985, S. 669 ff.;G. Kresze in Houben Weyl, Methods of Organic Chemistry, Vol. 25 Eil 1985, pp. 669 ff .;
K. Schank in Houben Weyl, Methoden der Organischen Chemie, Bd.K. Schank in Houben Weyl, Methods of Organic Chemistry, Vol.
Eil 1985, S. 1129 ff.;Eil 1985, p. 1129 ff .;
M. Takaya et al., Yakugaku Zasshi 9_8, 1530 (1978).M. Takaya et al., Yakugaku Zasshi 9_8, 1530 (1978).
30 Geeignete Lösungsmittel sind z.B. Wasser, Schwefelsäure, Essigsäure, Trifluoressigsäure oder halogenierte Kohlenwasserstoffe wie Dichlormethan und Chloroform.30 Suitable solvents are e.g. Water, sulfuric acid, acetic acid, trifluoroacetic acid or halogenated hydrocarbons such as dichloromethane and chloroform.
Normalerweise, gelingt die Oxidation bei Temperaturen von 0 bis 35 100°C.Normally, the oxidation succeeds at temperatures from 0 to 35 100 ° C.
Soll die Oxidation auf der Stufe des Sulfoxids angehalten werden, so arbeitet man vorzugsweise mit äquimolaren Mengen des Oxida- tionsmittels; ist die Oxidation zum Sulfon erwünscht, so werden 40 mindestens zwei Äquivalente des Oxidationsmittels, besser aber ein Überschuß eingesetzt.If the oxidation is to be stopped at the sulfoxide stage, one preferably works with equimolar amounts of the oxidizing agent; if oxidation to the sulfone is desired, at least two equivalents of the oxidizing agent, but better an excess, are used.
Syntheseschritt 3 ist die Substitution des Chlor in der 4 -Position durch Reaktion mit Ammoniak oder einem (Di) alkylamin. Reak- 45 tionen dieser Art sind allgemein bekannt, beispielsweise aus der folgenden Literatur: M. Takaya et al . , Yakugaku Zasshi 9 ./ 1530 (1978);Synthesis step 3 is the substitution of the chlorine in the 4 position by reaction with ammonia or a (di) alkylamine. Reactions of this type are generally known, for example from the following literature: M. Takaya et al. , Yakugaku Zasshi 9/1530 (1978);
V. Konecny et al . , Coll. Czech. Chem. Commun. 5TJ, 492 (1985).V. Konecny et al. , Coll. Czech. Chem. Commun. 5TJ, 492 (1985).
Die Reaktion kann in einer Vielzahl von Lösungsmitteln erfolg- reich durchgeführt werden, beispielsweise in Tetrahydrofuran, tert. Butylmethylether, Toluol, Methanol, Ethanol, Acetonitril, N,N-Dimethylformamid.The reaction can be carried out successfully in a variety of solvents, for example in tetrahydrofuran, tert. Butyl methyl ether, toluene, methanol, ethanol, acetonitrile, N, N-dimethylformamide.
Die Reaktionstemperatur liegt für n = 0 normalerweise bei 20 bis 150°C, für n = 0 oder 1 normalerweise bei (-10) bis 100°C, vorzugsweise 0 bis 50°C.The reaction temperature for n = 0 is normally 20 to 150 ° C, for n = 0 or 1 normally (-10) to 100 ° C, preferably 0 to 50 ° C.
Zur Erzielung einer ausreichend hohen Reaktionsgeschwindigkeit wird das Amin für den Fall n = 0 vorteilhaft im großen Überschuß eingesetzt, für n = 1 oder 2 reichen stöchiometrische Mengen, jedoch kann mit überschüssigem Amin häufig eine verbesserte Ausbeute erreicht werden.In order to achieve a sufficiently high reaction rate, the amine is advantageously used in large excess for the case n = 0, and stoichiometric amounts are sufficient for n = 1 or 2, but an improved yield can often be achieved with excess amine.
Normalerweise sind die substituierten Pyridazinone I nach dem vorstehend genannten Syntheseverfahren herstellbar. Aus wirtschaftlichen oder verfahrenstechnischen Gründen kann es jedoch zweckmäßiger sein, einige Verbindungen I aus ähnlichen Pyridazi - nonen, die sich jedoch in der Bedeutung eines Restes unterscheiden, herzustellen.The substituted pyridazinones I can normally be prepared by the synthesis process mentioned above. For economic or procedural reasons, however, it may be more expedient to prepare some compounds I from similar pyridaziones, but which differ in the meaning of a radical.
Die Aufarbeitung der Reaktionsgemische erfolgt in der Regel nach an sich bekannten Methoden, beispielsweise durch Verdünnen der Reaktionslösung mit Wasser und anschließender Isolierung des Produktes mittels Filtration, Kristallisation oder Lösungsmittelextraktion, oder durch Entfernen des Lösungsmittels, Verteilen des Rückstandes in einem Gemisch aus Wasser und einem geeigneten organischen Lösungsmittel und Aufarbeiten der organischen Phase auf das Produkt hin. «The reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or solvent extraction, or by removing the solvent, distributing the residue in a mixture of water and a suitable one organic solvents and working up the organic phase towards the product. «
Die substituierten Pyridazinone I können bei der Herstellung als Isomerengemische anfallen, die jedoch gewünschtenfalls nach den hierfür üblichen Methoden wie Kristallisation oder Chromatographie, auch an einem optisch aktiven Adsorbat, in die weitgehend reinen Isomeren getrennt werden können. Reine optisch aktive Isomere lassen sich vorteilhaft aus entsprechenden optisch aktiven Ausgangsprodukten herstellen.The substituted pyridazinones I can be obtained in the preparation as isomer mixtures, which, however, if desired, can be separated into the largely pure isomers by the customary methods such as crystallization or chromatography, including on an optically active adsorbate. Pure optically active isomers can advantageously be prepared from corresponding optically active starting products.
Landwirtschaftlich brauchbare Salze der Verbindungen I können durch Reaktion mit einer Base des entsprechenden Kations, vorzugsweise einem Alkalimetallhydroxid oder -hydrid, gebildet werden. Salze von I, deren Metallion kein Alkalimetallion ist, können auch durch Umsalzen des entsprechenden Alkalimetallsalzes in üblicher Weise hergestellt werden, ebenso Ammonium-, Phosphonium- , Sulfonium- und Sulfoxoniumsalze mittels Ammoniak, Phosphonium-, Sulfonium- oder Sulfoxoniumhydroxiden.Agricultural salts of the compounds I can be formed by reaction with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride. Salts of I, the metal ion of which is not an alkali metal ion, can also be prepared in a conventional manner by salting the corresponding alkali metal salt, as can ammonium, phosphonium, sulfonium and sulfoxonium salts using ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
Die Verbindungen I und deren landwirtschaftlich brauchbaren Salze eignen sich - sowohl als Isomerengemische als auch in Form der reinen Isomeren - als Herbizide. Die I enthaltenden herbiziden Mittel bekämpfen Pflanzenwuchs auf Nichtkulturflächen sehr gut, besonders bei hohen Aufwandmengen. In Kulturen wie Weizen, Reis, Mais, Soja und Baumwolle wirken sie gegen Unkräuter und Schadgräser, ohne die Kulturpflanzen nennenswert zu schädigen. Dieser Effekt tritt vor allem bei niedrigen Aufwandmengen auf.The compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides. The herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen I bzw. sie enthaltenden herbiziden Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgende Kulturen:Depending on the particular application method, the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants. The following crops are considered, for example:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis , Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica) , Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) , Helianthus annuus, Hevea brasiliensis , Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica) , .£>lea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus co munis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgäre), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera und Zea mays .Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea libericaus), Cucumodison , Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoealumisisumisum , Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica),. £> lea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium , Prunus persica, Pyrus co munis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
Darüber hinaus können die Verbindungen I auch in Kulturen, die durch Züchtung einschließlich gentechnischer Methoden gegen die Wirkung von Herbiziden tolerant sind, verwandt werden. Des weiteren eignen sich die substituierten Pyridazinone I auch zur Desikkation und/oder Defoliation von Pflanzen.In addition, the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods. The substituted pyridazinones I are also suitable for the desiccation and / or defoliation of plants.
Als Desikkantien eignen sie sich insbesondere zur Austrocknung der oberirdischen Teile von Kulturpflanzen wie Kartoffel, Raps, Sonnenblume und Sojabohne. Damit wird ein vollständig mechanisches Beernten dieser wichtigen Kulturpflanzen ermöglicht.As desiccants, they are particularly suitable for drying out the above-ground parts of crops such as potatoes, rapeseed, sunflower and soybeans. This enables a fully mechanical harvesting of these important crops.
Von wirtschaftlichem Interesse ist ferner die Ernteerleichterung, die durch das zeitlich konzentrierte Abfallen oder Vermindern der Haftfestigkeit am Baum bei Zitrusfrüchten, Oliven oder bei anderen Arten und Sorten von Kern-, Stein- und Schalenobst ermöglicht wird. Derselbe Mechanismus, das heißt die Förderung der Ausbildung von Trenngewebe zwischen Frucht- oder Blatt- und Sproßteil der Pflanzen ist auch für ein gut kontrollierbaresAlso of economic interest is the ease of harvesting, which is made possible by the temporally concentrated decrease or decrease in the adhesive strength on the tree in the case of citrus fruits, olives or other types and varieties of pome, stone and nuts. The same mechanism, that is, the promotion of the formation of separating tissue between the fruit or leaf and shoot part of the plants is also easy to control
Entblättern von Nutzpflanzen, insbesondere Baumwolle, wesentlich.Defoliation of crops, especially cotton, essential.
Außerdem führt die Verkürzung des Zeitintervalls, in dem die einzelnen Baumwollpflanzen reif werden, zu einer erhöhten Faser- qualität nach der Ernte.In addition, the shortening of the time interval in which the individual cotton plants ripen leads to increased fiber quality after the harvest.
Die Verbindungen I bzw. die sie enthaltenden Mittel können beispielsweise in Form von direkt versprühbaren wäßrigen Lösungen, Pulvern, Suspensionen, auch hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen oder Dispersionen, Emulsionen, Oldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The compounds I or the compositions comprising them can be sprayed, atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, sprays or granules. Dusting, scattering or pouring can be used. The application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Als inerte Hilfsstoffe kommen im Wesentlichen in Betracht: Mineralölfraktionen von mittlerem bis hohem Siedepunkt wie Kero- sin und Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Paraffine, Tetrahydronaphthalin, alkylierte Naphthaline und deren Derivate, alkylierte Benzole und deren Derivate, Alkohole wie Methanol, Ethanol, Propanol, Butanol und Cyclohexanol , Ketone wie Cyclohexanon, stark polare Lösungs- mittel, z.B. Amine wie N-Methylpyrrolidon und Wasser.The following are essentially considered as inert auxiliaries: mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Suspensionen, Pasten, netzbaren Pulvern oder wasserdispergier- baren Granulaten durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Oldispersionen können die Substrate als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. For the production of emulsions, pastes or old dispersions, the substrates as such or dissolved in an oil or solvent, by means of wetting agents, adhesives, dispersants or emulsifiers in water be homogenized. However, it is also possible to prepare concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanolen sowie von Fettalkoholglykolether , Kondensationsprodukte von sulfoniertem Naphthalin und seiner Derivate mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxy- ethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenyl-, Tributylphenylpolyglykolether , Alkyl - arylpolyetheralkohole, Isotridecylalkohol , Fettalkoholethylen- oxid-Kondensate, ethoxyliertes Ricinusöl, Polyoxyethylen- oder Polyoxypropylenalkylether, Laurylalkoholpolyglykoletheracetat , Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.The alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols as well as of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl polyglycol ether, alkyl aryl polyether alcohols, isotridecyl ethoxylated, polyethyleneglyoxy alcohol, fatty alcohol alcohol, fatty alcohol alcohol, fatty alcohol Polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite waste liquor or methyl cellulose.
Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind Mineralerden wie Kiesel - säuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe uψi pflanzliche Produkte wie Getreidemehl, Baum- rinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.Granules, e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are mineral earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
Die Konzentrationen der Wirkstoffe I in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Im allgemeinen enthalten die Formulierungen etwa von 0,001 bis 98 Gew. -%, vorzugsweise 0,01 bis 95 Gew. -%, mindestens eines Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90 % bis 100%, vorzugsweise 95 % bis 100 % (nach NMR-Spektrum) eingesetzt . Die folgenden Formulierungsbeispiele verdeutlichen die Herstellung solcher Zubereitungen:The concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range. In general, the formulations contain from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum). The following formulation examples illustrate the preparation of such preparations:
I. 20 Gewichtsteile der Verbindung Nr. 1.2 werden in einer Mischung gelöst, die aus 80 Gewichtsteilen alkyliertem Benzol, 10 Gewichtsteilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure-N-monoethanol - amid, 5 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Rizinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew. -% des Wirkstoffs enthält.I. 20 parts by weight of compound no. 1.2 are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanol amide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 Parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
II. 20 Gewichtsteile der Verbindung Nr. 4.3 werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon, 30 Gewichtsteilen Isobutanol, 20 Gewichtsteilen des Anlagerungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctyl- phenol und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Rizinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew. -% des Wirkstoffs enthält.II. 20 parts by weight of compound no. 4.3 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide on 1 Mole of castor oil consists. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.
III. 20 Gewichtsteile des Wirkstoffs Nr. 1.2 werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclohexanon, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Rizinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew. -% des Wirkstoffs enthält.III. 20 parts by weight of active ingredient no. 1.2 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.
IV. 20 Gewichtsteile des Wirkstoffs Nr. 4.3 werden mit 3 Gewichtsteilen des Natriumsalzes der Diisobutyl- naphthalin-α-sulfonsäure, 17 Gewichtsteilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gewichtsteilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. Durch feines Verteilen der Mischung in 20000 Gewichtsteilen Wasser enthält man eine Spritzbrühe, die 0,1 Gew. -% des Wirkstoffs enthält. V. 3 Gewichtsteile des Wirkstoffs Nr. 1.2 werden mitIV. 20 parts by weight of active ingredient no. 4.3 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. A fine spray mixture containing 0.1% by weight of the active ingredient is obtained by finely distributing the mixture in 20,000 parts by weight of water. V. 3 parts by weight of active ingredient no. 1.2 are with
97 Gewichtsteilen feinteiligem Kaolin vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gew. -% des Wirkstoffs enthält.97 parts by weight of finely divided kaolin mixed. In this way, a dusting agent is obtained which contains 3% by weight of the active ingredient.
VI. 20 Gewichtsteile des Wirkstoffs Nr. 4.3 werden mitVI. 20 parts by weight of active ingredient No. 4.3 are with
2 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure, 8 Gewichtsteilen Fettalkohol-polyglykolether, 2 Gewichtsteilen Natriumsalz eines Phenol-Harnstoff-Formaldehyd- Kondensates und 68 Gewichtsteilen eines paraffinischen2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic
Mineralöls innig vermischt. Man erhält eine stabile ölige Dispersion.Mineral oil mixed intimately. A stable oily dispersion is obtained.
VII. 1 Gewichtsteil des Wirkstoffs Nr. 1.2 wird in einer Mischung gelöst, die aus 70 Gewichtsteilen Cyclohexanon, 20 Gewichtsteilen ethoxyliertem Isooctylphenol und 10 Gewichtsteilen ethoxyliertem Rizinusöl besteht. Man erhält ein stabiles Emulsionskonzentrat.VII. 1 part by weight of active ingredient No. 1.2 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
VIII. 1 Gewichtsteil des Wirkstoffs Nr. 4.3 wird in einerVIII. 1 part by weight of active ingredient no. 4.3 is in a
Mischung gelöst, die aus 80 Gewichtsteilen Cyclohexanon und 20 Gewichtsteilen Wettol® EM 31 (= nichtionischer Emulgator auf der Basis von ethoxyliertem Rizinusöl; BASF AG) besteht. Man erhält ein stabiles Emulsions- konzentrat.Dissolved mixture, which consists of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol ® EM 31 (= nonionic emulsifier based on ethoxylated castor oil; BASF AG). A stable emulsion concentrate is obtained.
Die Applikation der Wirkstoffe I bzw. der herbiziden Mittel kann im Vorauflauf- oder im Nachauflaufverfahren erfolgen. Sind die Wirkstoffe für gewisse Kulturpflanzen weniger verträglich, so können Ausbringungstechniken angewandt werden, bei welchen die herbiziden Mittel mit Hilfe der Spritzgeräte so gespritzt werden, daß die Blätter der empfindlichen Kulturpflanzen nach Möglichkeit nicht getroffen werden, während die Wirkstoffe auf die Blätter darunter wachsender unerwünschter Pflanzen oder die unbedeckte Bodenfläche gelangen (post-directed, lay-by) .The active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
Die Aufwandmengen an Wirkstoff I betragen je nach Bekämpfungs- ziel, Jahreszeit, Zielpflanzen und Wachs umsStadium 0,001 bis 3,0, vorzugsweise 0,01 bis 1,0 kg/ha aktive Substanz (a.S.).The application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (as specified), depending on the control target, the season, the target plants and the wax at the stage.
Zur Verbreiterung des Wirkungsspektrums und zur Erzielung synergistischer Effekte können die substituierten Pyridazinone I mit zahlreichen Vertretern anderer herbizider oder Wachstums - regulierender Wirkstoffgruppen gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als Mischungspartner 1,2,4-Thia- diazole, 1, 3 , 4-Thiadiazole, Amide, Aminophosphorsäure und deren Derivate, Aminotriazole, Anilide, Aryloxy-/Heteroaryloxyalkan- säuren und deren Derivate, Benzoesäure und deren Derivate, Benzo- thiadiazinone, 2 - (Hetaroyl/Aroyl) - 1 , 3 -cyclohexandione, Hetero- aryl-Aryl-Ketone, Benzylisoxazolidinone, meta-CF3-Phenylderivate, Carbamate, Chinolincarbonsäure und deren Derivate, Chloracet- 5 anilide, Cyclohexan-1 , 3-dionderivate, Diazine, Dichlorpropion- säure und deren Derivate, Dihydrobenzofurane, Dihydrofuran-3-one, Dinitroaniline, Dinitrophenole, Diphenylether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3 -Phenyl - uracile, Imidazole, Imidazolinone, N-Phenyl-3 , 4 , 5 , 6-tetrahydro-To broaden the spectrum of activity and to achieve synergistic effects, the substituted pyridazinones I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. For example, 1,2,4-thiadiazoles, 1, 3, 4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, aryloxy- / heteroaryloxyalkane acids and their derivatives, benzoic acid and their derivatives, benzothiadiazinones, 2 - (hetaroyl / aroyl) - 1, 3 -cyclohexanediones, hetero-aryl-aryl-ketones, benzylisoxazolidinones, meta-CF 3 -phenyl derivatives, carbamates, quinoline carboxylic acid and their Derivatives, chloroacet-5 anilides, cyclohexane-1, 3-dione derivatives, diazines, dichloropropionic acid and their derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, ureas uracile, imidazole, imidazolinone, N-phenyl-3, 4, 5, 6-tetrahydro-
10 phthalimide, Oxadiazole, Oxirane, Phenole, Aryloxy- und Hetero- aryloxyphenoxypropionsäureester, Phenylessigsäure und deren Derivate, 2-Phenylpropionsäure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyridincarbonsäure und deren Derivate, Pyrimidylether, Sulfonamide, Sulfonylharnstoffe,10 phthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetero-aryloxyphenoxypropionic acid esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acids and their derivatives, pyrimidyl ethers, sulfonamides, sulfonamides, sulfonamides
15 Triazine, Triazinone, Triazolinone, Triazolcarboxamide und Uracile in Betracht.15 triazines, triazinones, triazolinones, triazolecarboxamides and uraciles can be considered.
Außerdem kann es von Nutzen sein, die Verbindungen I allein oder in Kombination mit anderen Herbiziden auch noch mit weiterenIt may also be useful to use the compounds I alone or in combination with other herbicides with others
20 Pflanzenschutzmitteln gemischt, gemeinsam auszubringen, beispielsweise mit Mitteln zur Bekämpfung von Schädlingen oder phytopathogenen Pilzen bzw. Bakterien. Von Interesse ist ferner die Mischbarkeit mit Mineralsalzlösungen, welche zur Behebung von Ernahrungs- und Spurenelementmängeln eingesetzt werden. Es können20 pesticides mixed to apply together, for example with pest control or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. It can
25 auch nichtphytotoxische Öle und Olkonzentrate zugesetzt werden.25 non-phytotoxic oils and oil concentrates can also be added.
HerstellbeispieleManufacturing examples
Beispiel 1: 4 , 5 -Dichlor-2 - (2 , 3 -dichlor-4 -methoxybenzyl) -3 (2H) - 30 pyridazinon (Verfahren A)Example 1: 4,5-dichloro-2 - (2,3-dichloro-4-methoxybenzyl) -3 (2H) - 30 pyridazinone (process A)
5,0 g 4, 5-Dichlor-3 (2H) -pyridazinon, 8,2 g 2 , 3 -Dichlor-4 -methoxy- benzylbromid und 8,4 g fein pulverisiertes Kaliumcarbonat wurden in 140 ml N, NwDimethylformamid gelöst bzw. suspendiert und5.0 g of 4,5-dichloro-3 (2H) -pyridazinone, 8.2 g of 2,3-dichloro-4-methoxybenzyl bromide and 8.4 g of finely powdered potassium carbonate were dissolved in 140 ml of N, Nw dimethylformamide or suspended and
35 16 Std. bei 20°C gerührt. Dann wurde der Reaktionsansatz in 600 ml Eiswasser gegossen. Nach 30 Minuten wurden die ausgefallenen Kristalle abgetrennt, in Dichlormethan gelöst und über Kieselgel filtriert. Das Filtrat wurde bis zur Trockne eingeengt. Ausbeute: 10,0 g (weiße Kristalle); Schmp. 143 - 144°C.35 stirred at 20 ° C for 16 hours. Then the reaction mixture was poured into 600 ml of ice water. After 30 minutes the precipitated crystals were separated off, dissolved in dichloromethane and filtered through silica gel. The filtrate was evaporated to dryness. Yield: 10.0 g (white crystals); Mp 143-144 ° C.
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45 Beispiel 2: 4 -Chlor- 2 - (2 , 3 -dichlor -4 -methoxybenzyl) - 5 -methyl- thio-3 (2H) -pyridazinon und45 Example 2: 4-Chloro-2 - (2, 3 -dichloro-4-methoxybenzyl) - 5 -methylthio-3 (2H) -pyridazinone and
5-Chlor-2- (2 , 3 -dichlor-4 -methoxybenzyl) -4 -methyl- thio -3 (2H) -pyridazinon (Verfahren D) 55-chloro-2- (2,3-dichloro-4-methoxybenzyl) -4-methyl-thio -3 (2H) -pyridazinone (method D) 5
7,1 g des Reaktionsprodukts von Beispiel 1 und 1,4 g Natrium- methanthiolat wurden in einer Mischung aus 100 ml Tetrahydrofuran und 25 ml Wasser gelöst und 16 h bei 20°C gerührt. Dann wurde mit 300 ml Dichlormethan verdünnt, die Wasserphase abgetrennt 10 und noch einmal mit 50 ml Wasser gewaschen. Nach Trocknen über Natriumsulfat wurde eingeengt. Die Reinigung des Rohproduktes erfolgte mittels Kieselgelchromatographie (Laufmittel: Cyclo- hexan/Essigester = zuerst 10 : 1, dann 7 : 3). Zuerst wurde 5-Chlor-2- (2 , 3 -dichlor- 4 -methoxybenzyl) -4 -methylthio -3 (2H) - 15 pyridazinon (1,0 g (14 %) , Schmp.: 129°C) eluiert, dann7.1 g of the reaction product from Example 1 and 1.4 g of sodium methanethiolate were dissolved in a mixture of 100 ml of tetrahydrofuran and 25 ml of water and stirred at 20 ° C. for 16 h. The mixture was then diluted with 300 ml of dichloromethane, the water phase was separated off and washed again with 50 ml of water. After drying over sodium sulfate, the mixture was concentrated. The crude product was purified by means of silica gel chromatography (mobile phase: cyclohexane / ethyl acetate = first 10: 1, then 7: 3). 5-chloro-2- (2,3-dichloro-4-methoxybenzyl) -4-methylthio -3 (2H) - 15 pyridazinone (1.0 g (14%), mp: 129 ° C.) was eluted first, then
4-Chlor-2- (2 , 3 -dichlor -4 -methoxybenzyl) -5 -methyl hio- 3 (2H) - pyridazinon (4,1 g (56 %) , Schmp.: 175 - 177°C) .4-chloro-2- (2,3-dichloro-4-methoxybenzyl) -5 -methyl hio- 3 (2H) -pyridazinone (4.1 g (56%), mp: 175-177 ° C).
Beispiel 3: 4 -Chlor-2 - (2 , 3 -dichlor-4 -methoxybenzyl) -5 -methyl- 20 sulfonyl -3 (2H) -pyridazinon (Verfahren D)Example 3: 4-Chloro-2 - (2,3-dichloro-4-methoxybenzyl) -5-methyl-20 sulfonyl -3 (2H) -pyridazinone (method D)
3,8 g des Hauptprodukts aus Beispiel 2 und 7,7 g m-Chlorperben- zoesäure wurden in 80 ml Chloroform 10 Stunden unter Rückfluß gekocht und dann 16 Stunden bei 23°C gerührt. Nach Zugabe von3.8 g of the main product from Example 2 and 7.7 g of m-chloroperbenzoic acid were refluxed in 80 ml of chloroform for 10 hours and then stirred at 23 ° C. for 16 hours. After adding
25 80 ml 10 %iger wäßriger Natriumhydrogencarbonat -Lösung wurde das zweiphasige Gemisch intensiv durchgerührt. Die organische Phase wurde abgetrennt, zweimal mit je 30 ml NaHSθ3- Lösung (35 %ig in Wasser) , einmal mit 30 ml Natriumhydrogencarbonat -Lösung und dann mit 50 ml Wasser gewaschen. Nach Trocknen über Natriumsulfat25 80 ml of 10% aqueous sodium hydrogen carbonate solution, the two-phase mixture was stirred intensively. The organic phase was separated, washed twice with 30 ml of NaHSO 3 solution (35% in water), once with 30 ml of sodium hydrogen carbonate solution and then with 50 ml of water. After drying over sodium sulfate
30 wurde eingeengt. Die Reinigung des Rohproduktes erfolgte durch verrühren mit Diethylether . Ausbeute: 3,5 g (weiße Kristalle); Schmelzpunkt: 183°C.30 was concentrated. The crude product was purified by stirring with diethyl ether. Yield: 3.5 g (white crystals); Melting point: 183 ° C.
Beispiel 4: 4 -Amino-2 - (2 , 3 -dichlor-4 -methoxybenzyl) -5 -methyl- 35 sulfonyl -3 (2H) -pyridazinon (Verfahren D)Example 4: 4-amino-2 - (2,3-dichloro-4-methoxybenzyl) -5-methyl-35 sulfonyl -3 (2H) -pyridazinone (method D)
3 , 15 g des Reaktionsprodukts aus Beispiel 3 wurden in 90 ml Tetrahydrofuran gelöst, mit 90 ml 25 %iger wäßriger Ammoniaklösung versetzt und unter gutem Rühren fünf Stunden unter Rück- 40 fluß gekocht. Dann wurde die organische Phase abgetrennt, mit Wasser gewaschen, über Natriumsulfat getrocknet und eingeengt. Der Rückstand wurde zuerst mit Diethylether, dann mit Aceton verrührt. Ausbeute: 2,1 g (weiße Kristalle); Schmp.: 222 - 223°C.3.15 g of the reaction product from Example 3 were dissolved in 90 ml of tetrahydrofuran, mixed with 90 ml of 25% strength aqueous ammonia solution and refluxed for five hours with thorough stirring. The organic phase was then separated off, washed with water, dried over sodium sulfate and concentrated. The residue was stirred first with diethyl ether, then with acetone. Yield: 2.1 g (white crystals); Mp: 222 - 223 ° C.
45 Vorstufe: 4 , 5 -Dichlor- 2 - (4 -nitrobenzyl) -3 (2H) -pyridazinon (Verfahren A) , bekannt aus DE-A 42 43 38145 Precursor: 4,5-dichloro-2 - (4 -nitrobenzyl) -3 (2H) -pyridazinone (process A), known from DE-A 42 43 381
20,0 g 4 , 5 -Dichlor-3 (2H) -pyridazinon, 33,5 g Kaliumcarbonat und 5 26,2 g 4 -Nitrobenzylbromid wurden in 420 ml wasserfreiem N,N- Dimethylformamid sechs Stunden bei 23°C gerührt. Dann wurde die Reaktionsmischung in 2 1 Eiswasser gegossen und gut verrührt. Die ausgefallenen Kristalle wurden abgetrennt, mit Wasser gewaschen, getrocknet und durch Chromatographie an Kieselgel (Elutions- 10 mittel: Dichlormethan) gereinigt. Ausbeute: 33,4 g (weiße Kristalle); Schmp.: 131°C.20.0 g of 4,5-dichloro-3 (2H) -pyridazinone, 33.5 g of potassium carbonate and 5 26.2 g of 4-nitrobenzyl bromide were stirred in 420 ml of anhydrous N, N-dimethylformamide at 23 ° C. for six hours. Then the reaction mixture was poured into 2 l of ice water and stirred well. The precipitated crystals were separated off, washed with water, dried and purified by chromatography on silica gel (eluent: dichloromethane). Yield: 33.4 g (white crystals); Mp: 131 ° C.
Beispiel 5: 4 -Chlor-5 -methylthio-2 - (4 -nitrobenzyl) - 3 (2H) - pyridazinon und 5 -Chlor-4 -methylthio-2 - (4 -nitro- 15 benzyl) -3 (2H) -pyridazinon (Verfahren D)Example 5: 4-Chloro-5-methylthio-2 - (4-nitrobenzyl) - 3 (2H) - pyridazinone and 5-chloro-4-methylthio-2 - (4 -nitro-15 benzyl) -3 (2H) - pyridazinone (method D)
Zu einer Lösung von 30,0 g 4 , 5 -Dichlor -2 - (4 -nitrobenzyl) -3 (2H) - pyridazinon in 500 ml Tetrahydrofuran wurde eine Lösung von 7,7 g Natriummethanthiolat in 125 ml Wasser getropft und anschließendA solution of 7.7 g of sodium methanethiolate in 125 ml of water was added dropwise to a solution of 30.0 g of 4,5-dichloro -2 - (4-nitrobenzyl) -3 (2H) -pyridazinone in 500 ml of tetrahydrofuran and then
20 16 Stunden bei 23°C und 7 Stunden unter Rückfluß gerührt. Nach Einengen wurde der Rückstand in Dichlormethan aufgenommen, mit Wasser gewaschen, über Na2S04 getrocknet und eingedampft. Der zurückbleibende Feststoff wurde mit Diethylether ausgekocht. Zurück blieben 16 g weiße Kristalle vom Schmp. 204°C (4 -Chlor -5 -methyl -20 16 hours at 23 ° C and 7 hours under reflux. After concentration, the residue was taken up in dichloromethane, washed with water, dried over Na 2 S0 4 and evaporated. The remaining solid was boiled out with diethyl ether. 16 g of white crystals of mp. 204 ° C. (4-chlorine-5-methyl -
25 thio ) . Die Etherphase wurde eingeengt und der Rückstand an Kieselgel mit Cyclohexan/Essigester (10:1) chromatographiert . Man erhielt so 6,4 g weiße Kristalle vom Schmp. 126°C (5 -Chlor-4 -methylthio ) .25 thio). The ether phase was concentrated and the residue was chromatographed on silica gel with cyclohexane / ethyl acetate (10: 1). 6.4 g of white crystals of mp 126 ° C. (5-chloro-4-methylthio) were obtained in this way.
30 Beispiel 6: 4 , 5 -Dichlor-2 - (2 -nitrobenzyl) - 3 (2H) -pyridazinon (Verfahren A)30 Example 6: 4, 5 -Dichlor-2 - (2 -nitrobenzyl) - 3 (2H) -pyridazinone (Process A)
Zu einer Lösung von 19 , 1 g 4, 5 -Dichlor -3 (2H) -pyridazinon inTo a solution of 19.1 g of 4,5-dichloro-3 (2H) -pyridazinone in
250 ml wasserfreiem Dimethylformamid wurden 31,7 g fein gepulver-250 ml of anhydrous dimethylformamide were finely powdered 31.7 g
35 tes Kaliumcarbonat gegeben und eine Lösung von 25 g 2 -Nitrobenzylbromid in 200 ml Dimethylformamid zugetropft. Nach fünfstündigem Rühren bei 23°C wurde der Reaktionsansatz in 2 1 Eiswasser gegossen. Dabei fiel ein feiner Niederschlag aus, der abgetrennt und an Kieselgel mit Tetrahydrofuran/Dichlormethan 2 : 1 chroma-35 tes of potassium carbonate are added and a solution of 25 g of 2-nitrobenzyl bromide in 200 ml of dimethylformamide is added dropwise. After stirring for five hours at 23 ° C., the reaction mixture was poured into 2 l of ice water. A fine precipitate was formed, which was separated off and chromatographed on silica gel with tetrahydrofuran / dichloromethane 2: 1.
40 tographisch gereinigt wurde. Ausbeute: 32 g (weiße Kristalle) ; Schmp. : 199 - 201°C.40 was cleaned graphically. Yield: 32 g (white crystals); Mp: 199-201 ° C.
45 Anwendungsbeispiele (herbizide Wirksamkeit)45 Examples of use (herbicidal activity)
Die herbizide Wirkung der substituierten Pyridazinone I ließ sich durch die folgenden Gewächshausversuche zeigen: 5The herbicidal activity of the substituted pyridazinones I was demonstrated by the following greenhouse tests: 5
Als Kulturgefäße dienten Plastikblumentöpfe mit lehmigem Sand mit etwa 3,0 % Humus als Substrat. Die Samen der Testpflanzen wurden nach Arten getrennt eingesät.Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels. The seeds of the test plants were sown separately according to species.
10 Bei Vorauflaufbehandlung wurden die in Wasser suspendierten oder emulgierten Wirkstoffe direkt nach Einsaat mittels fein verteilender Düsen aufgebracht. Die Gefäße wurden leicht beregnet, um Keimung und Wachstum zu fördern, und anschließend mit durchsichtigen Plastikhauben abgedeckt, bis die Pflanzen angewachsen10 In pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles. The vessels were lightly sprinkled to promote germination and growth, and then covered with clear plastic covers until the plants grew
15 waren. Diese Abdeckung bewirkt ein gleichmäßiges Keimen der Test- pflanzen, sofern dies nicht durch die Wirkstoffe beeinträchtigt wurde.15 were. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
Zum Zweck der Nachauflaufbehandlung wurden die Testpflanzen 20 je nach Wuchsform erst bis zu einer Wuchshöhe von 3 bis 15 cm angezogen und erst dann mit den in Wasser suspendierten oder emulgierten Wirkstoffen behandelt. Die Testpflanzen wurden dafür entweder direkt gesät und in den gleichen Gefäßen aufgezogen oder sie wurden erst als Keimpflanzen getrennt angezogen und einige 25 Tage vor der Behandlung in die Versuchsgefäße verpflanzt. Die Aufwandmenge für die Nachauflaufbehandlung betrug 0,0625 oder 0,0313 kg/ha a.S. (aktive Substanz).For the purpose of post-emergence treatment, the test plants 20, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers some 25 days before the treatment. The application rate for post-emergence treatment was 0.0625 or 0.0313 kg / ha a.S. (active substance).
Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 bis 30 25°C bzw. 20 bis 35°C gehalten. Die Versuchsperiode erstreckte sich über 2 bis 4 Wochen. Während dieser Zeit wurden die Pflanzen gepflegt, und ihre Reaktion auf die einzelnen Behandlungen wurde ausgewertet.The plants were kept in a species-specific manner at temperatures of 10 to 30 25 ° C and 20 to 35 ° C. The trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
35 Bewertet wurde nach einer Skala von 0 bis 100. Dabei bedeutet 100 kein Aufgang der Pflanzen bzw. völlige Zerstörung zumindest der oberirdischen Teile und 0 keine Schädigung oder normaler Wachstumsverlauf .35 was rated on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
4040
45 Die in den Gewächshausversuchen verwendeten Pflanzen setzten sich aus folgenden Arten zusammen:45 The plants used in the greenhouse experiments are composed of the following types:
Figure imgf000055_0001
Figure imgf000055_0001
Bei Aufwandmengen von 0,0625 und 0,0313 kg/ha a.S. zeigte die Verbindung Nr. 1.2 im Nachauflaufverfahren eine sehr gute herbizide Wirkung gegen die o.g. breitblättrigen Pflanzen.At application rates of 0.0625 and 0.0313 kg / ha a.S. Compound No. 1.2 showed a very good herbicidal activity against the above broad-leaved plants.
Anwendungsbeispiele (desikkant/defoliante Wirksamkeit)Examples of use (desiccant / defolian effectiveness)
Als Testpflanzen dienten junge, 4-blättrige (ohne Keimblätter) Baumwollpflanzen, die unter Gewächshausbedingungen angezogen wurden (rel. Luftfeuchtigkeit 50 bis 70 %; Tag-/Nachttemperatur 27/20°C) .Young, 4-leafed (without cotyledons) cotton plants served as test plants, which were grown under greenhouse conditions (relative humidity 50 to 70%; day / night temperature 27/20 ° C.).
Die jungen Baumwollpflanzen wurden tropfnaß mit wässrigen Aufbereitungen der Wirkstoffe I (unter Zusatz von 0,15 Gew.-% des Fettalkoholalkoxylats Plurafac® LF 7001> , bezogen auf die Spritz- brühe) blattbehandelt. Die ausgebrachte Wassermenge betrug umgerechnet 1000 1/ha. Nach 13 Tagen wurde die Anzahl der abgeworfenen Blätter und der Grad der Entblätterung in % bestimmt.The young cotton plants were subjected to runoff (700 1> with the addition of 0.15 wt .-% of the fatty alcohol alkoxylate Plurafac LF ®, based on the spray mixture) sheet treated with aqueous preparations of the active compounds I. The amount of water applied was the equivalent of 1000 l / ha. After 13 days, the number of leaves dropped and the degree of defoliation in% were determined.
Bei den unbehandelten Kontrollpflanzen trat kein Blattfall aufNo leaf fall occurred in the untreated control plants
ein schaumarmes, nichtionisches Tensid der BASF AG a low-foaming, nonionic surfactant from BASF AG

Claims

Patentansprücheclaims
1. Substituierte Pyridazinone der allgemeinen Formel I1. Substituted pyridazinones of the general formula I
Figure imgf000056_0001
Figure imgf000056_0001
in der die Substituenten folgende Bedeutungen haben:in which the substituents have the following meanings:
R^—R3 unabhängig voneinander Wasserstoff, Nitro, Hydroxy, Halogen, Cχ-Cg-Alkoxy, Cχ-Cg-Halogenalkoxy, SH, Cχ-Cg-Alkylthio, Cχ-Cg-Halogenalkylthio, Amino, Cχ-Cg-Alkylamino, Di- (Cχ-Cg-alkyl) amino, Cyano, Cχ-Cg-Alkyl, Cχ-Cg-Halogenalkyl, Cχ-C6-Alkylsulfinyl, Cχ-Cg-Alkylsulfonyl, Cχ-Cg-Halogenalkylsulfinyl oderR ^ —R 3 independently of one another hydrogen, nitro, hydroxy, halogen, Cχ-Cg-alkoxy, Cχ-Cg-haloalkoxy, SH, Cχ-Cg-alkylthio, Cχ-Cg-haloalkylthio, amino, Cχ-Cg-alkylamino, Di - (Cχ-Cg-alkyl) amino, cyano, Cχ-Cg-alkyl, Cχ-Cg-haloalkyl, Cχ-C 6 -alkylsulfinyl, Cχ-Cg-alkylsulfonyl, Cχ-Cg-haloalkylsulfinyl or
Cχ-Cg-Halogenalkylsulfonyl ;Cχ-Cg haloalkylsulfonyl;
R4, R5 Wasserstoff oder gemeinsam zusammen mit dem C-Atom, an das sie gebunden sind, eine Carbonylgruppe;R 4 , R 5 are hydrogen or, together with the carbon atom to which they are attached, a carbonyl group;
R6 Wasserstoff, Nitro oder Halogen;R 6 is hydrogen, nitro or halogen;
R7 Wasserstoff, Nitro, Halogen, COOH, Cχ-Cg-Alkoxy,R 7 is hydrogen, nitro, halogen, COOH, Cχ-Cg-alkoxy,
(Cχ-Cg-Alkoxy) carbonyl oder (Cχ-Cg-Alkoxy) carbonyl- Cχ-Cg- ( alkoxy) carbonyl ;(Cχ-Cg-alkoxy) carbonyl or (Cχ-Cg-alkoxy) carbonyl-Cχ-Cg- (alkoxy) carbonyl;
R8 Wasserstoff, Nitro oder OR8' ;R 8 is hydrogen, nitro or OR 8 ';
R8' Wasserstoff, Cχ-C6-Alkyl, C3-Cg-Cycloalkyl , Cχ-C6-Halo- genalkyl, Cyano- (Cχ-Cg-Alkyl) , Cχ-C6-Alkoxy-Cχ-C6-alkyl,R 8 'is hydrogen, Cχ-C 6 -alkyl, C 3 -Cg-cycloalkyl, Cχ-C 6 -halogenoalkyl, cyano- (Cχ-Cg-alkyl), Cχ-C 6 -alkoxy-Cχ-C 6 - alkyl,
C1-C4-Alkylthio-Cχ-C4-alkyl/ Cχ-C4-Alkylsulfinyl-Cχ-C - alkyl, Cχ-C4-Alkylsulfonyl-Cχ-C -alkyl, C3-Cg-Alkenyl, Cs-Cg-Cycloalkenyl, C3-Cg-Halogenalkenyl , C3-Cg-Alkinyl ,C 1 -C 4 alkylthio-Cχ-C 4 -alkyl / Cχ-C 4 -alkylsulfinyl-Cχ-C - alkyl, Cχ-C 4 -alkylsulfonyl-Cχ-C -alkyl, C3-Cg-alkenyl, Cs-Cg -Cycloalkenyl, C3-Cg-haloalkenyl, C 3 -Cg-alkynyl,
Phenyl-Cχ-Cg-alkyl, wobei der Phenylring ein bis dreiPhenyl-Cχ-Cg-alkyl, wherein the phenyl ring one to three
Substituenten aus der Gruppe Halogen, Cχ-C4-Alkyl, Cχ-C -Halogenalkyl, Hydroxy, Cχ-C -Alkoxy, Cχ-C4-Halo- genalkoxy, (Cχ-C4~Alkoxy) carbonyl-Cχ-C4-alkoxy, Nitro, Cyano, COOH und (Cχ-C4-Alkoxy) carbonyl tragen kann, Carboxyl-Cχ-C4-alkyl, (Cχ-C4-Alkoxy) carbonyl-Cχ-C4- alkyl, (C3~Cg-Alkenyloxy) carbonyl-Cχ-C4-alkyl, (C3-Cg-Alkinyloxy) carbonyl-Cχ-C4-alkyl, Cχ-C4-Alkoxy- (Cχ-C4-alkoxy) carbonyl-Cι-C4-alkyl , (Cχ-C4-Halogen- alkoxy) carbonyl-Cχ-C4-alkyl, (C3-Cg-Cycloalkoxy) - carbonyl-Cχ-C4~alkyl , (Cχ-C4-Alkoxy) carbonyl- (Cχ-C4-alk- oxy) carbonyl-Cχ-C4-alkyl , (C3-Cg-Alkenyloxy) carbonyl- (Cχ-C4-alkoxy) carbonyl-Cχ-C4-alkyl , (C3-Cg-Alkinyloxy) - carbonyl- (Cχ-C4~alkoxy) carbonyl-Cχ-C4-alkyl , Carboxyl- (Cχ-C4-alkoxy) carbonyl-Cχ-C4-alkyl, Phenoxycarbonyl-Substituents from the group halogen, Cχ-C 4 -alkyl, Cχ-C -haloalkyl, hydroxy, Cχ-C -alkoxy, Cχ-C 4 -haloalkoxy, (Cχ-C 4 ~ alkoxy) carbonyl-Cχ-C 4 -alkoxy, nitro, cyano, COOH and (Cχ-C 4 -alkoxy) carbonyl can wear, Carboxyl-Cχ-C 4 -alkyl, (Cχ-C 4 -alkoxy) carbonyl-Cχ-C 4 -alkyl, (C 3 ~ Cg-alkenyloxy) carbonyl-Cχ-C 4 -alkyl, (C 3 -Cg-alkynyloxy ) carbonyl-Cχ-C 4 -alkyl, Cχ-C 4 -alkoxy- (Cχ-C 4 -alkoxy) carbonyl-Cι-C 4 -alkyl, (Cχ-C 4 -haloalkoxy) carbonyl-Cχ-C 4 -alkyl, (C 3 -Cg-cycloalkoxy) - carbonyl-Cχ-C 4 ~ alkyl, (Cχ-C 4 -alkoxy) carbonyl- (Cχ-C 4 -alk-oxy) carbonyl-Cχ-C 4 -alkyl, (C 3 -Cg-alkenyloxy) carbonyl- (Cχ-C 4 -alkoxy) carbonyl-Cχ-C 4 -alkyl, (C 3 -Cg-alkynyloxy) - carbonyl- (Cχ-C 4 ~ alkoxy) carbonyl-Cχ- C 4 -alkyl, carboxyl- (Cχ-C 4 -alkoxy) carbonyl-Cχ-C 4 -alkyl, phenoxycarbonyl-
Cχ-C4-alkyl , Benzyloxycarbonyl-Cχ-C4-alkyl ,Cχ-C 4 alkyl, benzyloxycarbonyl-Cχ-C 4 alkyl,
-CH(R9) -CO-OCH (COOR10) -COOR10, -CH (R9 ) -CO-N (R11) R12 ; "CH(R9)-CO-R13, -CH(R9)C(R13)=N-OR14, -CH (R9) -CO-COOR10 , -CH(R9)-C(COOR1Q)=N-OR14,-CH (R 9 ) -CO-OCH (COOR 10 ) -COOR 10 , -CH (R 9 ) -CO-N (R 11 ) R 12 ; "CH (R 9 ) -CO-R 13 , -CH (R 9 ) C (R 13 ) = N-OR 14 , -CH (R 9 ) -CO-COOR 10 , -CH (R 9 ) -C ( COOR 1Q ) = N-OR 14 ,
-CH (R9 ) -CO-N [CH (R9 ) -COOR10] -OR14 , "CH(R9)-C [-OCH(R9) -COOR10] =N-OR14 ,-CH (R 9 ) -CO-N [CH (R 9 ) -COOR 10 ] -OR 14 , " CH (R 9 ) -C [-OCH (R 9 ) -COOR 10 ] = N-OR 14 ,
Figure imgf000057_0001
Figure imgf000057_0001
R9,R10, R13, R15-R19 unabhängig voneinander Wasserstoff oder Cχ-C5-Alkyl;R 9 , R 10 , R 13 , R 15 -R 19 independently of one another are hydrogen or Cχ-C 5 -alkyl;
R11, R12 unabhängig voneinander Wasserstoff, Cχ-Cg-Alkyl,R 11 , R 12 independently of one another are hydrogen, Cχ-Cg-alkyl,
Carboxyl-Cχ-C4-alkyl , (Cχ-C4~Alkoxy) carbonyl-Cχ-C4~ alkyl, Cg-C14-Aryl, Phenyl-Cχ-C4-alkyl , oder R11 und R12 bilden zusammen eine Tetramethylen- Pentamethylen oder Ethylenoxyethylenkette, die ggf. mit einer Carboxyl - gryppe oder einem (Cχ-Cg-Alkoxy) carbonylrest substi- tuiert ist;Carboxyl-Cχ-C 4 alkyl, (Cχ-C 4 ~ alkoxy) carbonyl-Cχ-C 4 ~ alkyl, Cg-C 14 aryl, phenyl-Cχ-C 4 alkyl, or R 11 and R 12 together a tetramethylene-pentamethylene or ethyleneoxyethylene chain, which is optionally substituted with a carboxyl group or a (Cχ-Cg-alkoxy) carbonyl radical;
R14 Wasserstoff, Cχ-Cg-Alkyl, Carboxyl -C -C -alkyl oder (Ci -Cg -Alkoxy) carbonyl ~Cχ -Cg - alkyl ;R 14 is hydrogen, Cχ-Cg-alkyl, carboxyl -C -C alkyl or (Ci -Cg alkoxy) carbonyl ~ Cχ -Cg alkyl;
R20 für R8 = H oder NO2 : Wasserstoff oder Halogen; für R8 = OR8': Halogen;R 20 for R 8 = H or NO 2 : hydrogen or halogen; for R 8 = OR 8 ': halogen;
R21 Wasserstoff oder Halogen,R 21 is hydrogen or halogen,
sowie die landwirtschaftlich brauchbaren Salze der Verbindungen I, ausgenommen 4 , 5-Dichlor-2- (4-nitrobenzoyl) -3 (2H) -pyridazinon und 4 , 5-Dichlor-2- (4-nitrobenzyl) -3 (2H) -pyridazinon.and the agriculturally useful salts of the compounds I, except 4,5-dichloro-2- (4-nitrobenzoyl) -3 (2H) -pyridazinone and 4,5-dichloro-2- (4-nitrobenzyl) -3 (2H) -pyridazinone.
2. Substituierte Pyridazinone der Formel I nach Anspruch 1, wobei die Substituenten folgende Bedeutungen haben:2. Substituted pyridazinones of formula I according to claim 1, wherein the substituents have the following meanings:
R1 Wasserstoff, Halogen, Cχ-Cg-Alkoxy, Cχ-Cg-Alkylthio, Amino, Cχ-Cg-Alkylamino oder Di- (C -Cg-alkyl) amino;R 1 is hydrogen, halogen, Cχ-Cg-alkoxy, Cχ-Cg-alkylthio, amino, Cχ-Cg-alkylamino or di- (C -Cg-alkyl) amino;
R2 Halogen, Cχ-C6-Alkyl, Cχ-C5-Halogenalkyl, C -C5-Alkyl- thio, Cχ-Cg-Alkylsulfinyl oder Cχ-Cg-Alkylsulfonyl ;R 2 halogen, Cχ-C 6 alkyl, Cχ-C 5 haloalkyl, C -C 5 alkyl thio, Cχ-Cg-alkylsulfinyl or Cχ-Cg-alkylsulfonyl;
R3 Wasserstoff, Hydroxy, Cχ-Cg-Alkyl oder Cχ-Cg-Alkoxy;R 3 is hydrogen, hydroxy, Cχ-Cg-alkyl or Cχ-Cg-alkoxy;
R -R7 Wasserstoff;R -R 7 is hydrogen;
R8 OR8 ' ;R 8 OR 8 ';
R8' Wasserstoff, Cχ-Cg-Alkyl, C3-Cg-Cycloalkyl, Cyano- (Cχ-Cg-alkyl) , C3-C5-Alkenyl, C3-Cg-Alkinyl , Carboxyl-R 8 'is hydrogen, Cχ-Cg-alkyl, C 3 -Cg-cycloalkyl, cyano- (Cχ-Cg-alkyl), C 3 -C 5 -alkenyl, C 3 -Cg-alkynyl, carboxyl-
Cχ-C4-alkyl, (Cχ-C4-Alkoxy) carbonyl-Cχ-C4-alkyl, (C3-C6-Alkenyloxy) carbonyl-C -C4-alkyl , (C3-Cg-Alkinyl - oxy) carbonyl-Cχ-C4-alkyl , Cχ-C4-Alkoxy- (Cχ-C4-alk- oxy) carbonyl-C -C4-alkyl, (Cχ-C4-Alkoxy) carbonyl- (C -C4-alkoxy) carbonyl-Cχ-C4-alkyl, Carboxyl- (Cχ-C4- alkoxy) carbonyl-Cχ-C4-alkyl, -CH (R9) -C (COOR10) =N-OR14, -CH(R9) -CO-N [CH(R9) -COOR10] -OR14, -CH (R9) -C [-0CH(R9) -COOR10] =N-OR14;Cχ-C 4 -alkyl, (Cχ-C 4 -alkoxy) carbonyl-Cχ-C 4 -alkyl, (C 3 -C 6 -alkenyloxy) carbonyl-C -C 4 -alkyl, (C 3 -Cg-alkynyl - oxy) carbonyl-Cχ-C 4 -alkyl, Cχ-C 4 -alkoxy- (Cχ-C 4 -alk-oxy) carbonyl-C -C 4 -alkyl, (Cχ-C 4 -alkoxy) carbonyl- (C - C 4 -alkoxy) carbonyl-Cχ-C 4 -alkyl, carboxyl- (Cχ-C 4 - alkoxy) carbonyl-Cχ-C 4 -alkyl, -CH (R 9 ) -C (COOR 10 ) = N-OR 14 , -CH (R 9 ) -CO-N [CH (R 9 ) -COOR 10 ] -OR 14 , -CH (R 9 ) -C [-0CH (R 9 ) -COOR 10 ] = N-OR 14 ;
R9 , R10 unabhängig voneinander Was s ers tof f oder Cχ-Cg-Alkyl ;R 9 , R 10 independently of one another Was s ers tof f or Cχ-Cg-alkyl;
R11 , R12 unabhängig voneinander Was sers tof f , Cχ-C6-Alkyl ,R 11 , R 12 independently of one another Was sers tof f, Cχ-C 6 alkyl,
Cawrboxyl-Cχ-C4-alkyl oder ( Cχ-C4-Alkoxy) carbonyl-Cχ-C4- alkyl ;Ca w rboxyl-Cχ-C4-alkyl or (Cχ-C 4 -alkoxy) carbonyl-Cχ-C 4 - alkyl;
R14 Cχ-Cg-Alkyl ;R 14 Cχ-Cg-alkyl;
R20 Chlor oder Brom;R 20 chlorine or bromine;
R21 Wasserstoff oder Chlor. R 21 is hydrogen or chlorine.
3. Substituierte Pyridazinone der Formel I nach Anspruch 1, wobei die Substituenten folgende Bedeutungen haben:3. Substituted pyridazinones of formula I according to claim 1, wherein the substituents have the following meanings:
R1 Wasserstoff, Halogen, Cχ-Cg-Alkoxy, Cχ-Cg-Alkylthio, Amino, Cχ-Cg-Alkylamino oder Di- (Cχ-Cg-alkyl) amino;R 1 is hydrogen, halogen, Cχ-Cg-alkoxy, Cχ-Cg-alkylthio, amino, Cχ-Cg-alkylamino or di- (Cχ-Cg-alkyl) amino;
R2 Halogen, Cχ-C6-Alkyl, Cχ-C6-Halogenalkyl, C -C6-Alkyl- thio, Cχ-Cg-Alkylsulfinyl oder Cχ-Cg-Alkylsulfonyl ;R 2 halogen, Cχ-C 6 alkyl, Cχ-C 6 haloalkyl, C -C 6 alkyl thio, Cχ-Cg-alkylsulfinyl or Cχ-Cg-alkylsulfonyl;
R3 Wasserstoff, Hydroxy, Cχ-Cg-Alkyl oder Cχ-Cg-Alkoxy;R 3 is hydrogen, hydroxy, Cχ-Cg-alkyl or Cχ-Cg-alkoxy;
4_ 6 Wasserstoff;4_ 6 hydrogen;
R7 Wasserstoff, Carboxyl, (Cχ-Cg-Alkoxy) carbonyl, (Cχ-Cg-Alkoxy) carbonyl- (Cχ-Cg-alkoxy) carbonyl oderR 7 is hydrogen, carboxyl, (Cχ-Cg-alkoxy) carbonyl, (Cχ-Cg-alkoxy) carbonyl- (Cχ-Cg-alkoxy) carbonyl or
Cχ-Cg-Alkoxy;Cχ-Cg alkoxy;
R8 Nitro;R 8 nitro;
R20, R21 unabhängig voneinander Wasserstoff, Chlor oder Brom.R 20 , R 21 independently of one another are hydrogen, chlorine or bromine.
4. Substituierte Pyridazinone der Formel I nach Anspruch 1, wobei die Substituenten folgende Bedeutungen haben:4. Substituted pyridazinones of formula I according to claim 1, wherein the substituents have the following meanings:
R1 Amino;R 1 amino;
R2 C -C6-Alkylthio, Cχ-Cg-Alkylsulfinyl oder Cχ-Cg-Alkyl- sulfonyl;R 2 C -C 6 alkylthio, Cχ-Cg-alkylsulfinyl or Cχ-Cg-alkylsulfonyl;
R3-R7 Wasserstoff;R 3 -R 7 hydrogen;
R8 OR8';R 8 OR 8 ';
R8' Wasserstoff, Cχ-Cg-Alkyl, C3-Cg-Cycloalkyl, Cyano- (Ci-Cg-alkyl) , C3-Cg-Alkenyl, C3-Cg-Alkinyl, Carboxyl-R 8 'is hydrogen, Cχ-Cg-alkyl, C 3 -Cg-cycloalkyl, cyano- (Ci-Cg-alkyl), C 3 -Cg-alkenyl, C 3 -Cg-alkynyl, carboxyl-
Cχ-C4-alkyl , (Cχ-C4-Alkoxy) carbonyl-Cχ-C4-alkyl , (C3-Cg-Alkenyloxy) carbonyl-Cχ-C4-alkyl, (C3-Cg-Alkinyl- oxy) carbonyl-Cχ-C4-alkyl, Cχ-C4-Alkoxy- (Cχ-C4-alk- oxy) carbonyl-Cχ-C4-alkyl , (Cχ-C4-Alkoxy) carbonyl- (Cχ-C4-alkoxy) carbonyl-Cχ-C -alkyl, Carboxyl- (Cχ-C4~ alkoxy) carbonyl-Cχ-C4-alkyl, -CH(R9) -C (COOR10) =N-OR14, -CH(R9) -CO-N[CH(R9) -COOR10] -OR14, -CH (R9) -C [-OCH(R9) -COOR10] =N-OR14; R9,R10 unabhängig voneinander Wasserstoff oder Cχ-Cg-Alkyl;Cχ-C 4 -alkyl, (Cχ-C 4 -alkoxy) carbonyl-Cχ-C 4 -alkyl, (C 3 -Cg-alkenyloxy) carbonyl-Cχ-C 4 -alkyl, (C 3 -Cg-alkynyloxy) ) carbonyl-Cχ-C 4 -alkyl, Cχ-C 4 -alkoxy- (Cχ-C 4 -alk-oxy) carbonyl-Cχ-C 4 -alkyl, (Cχ-C 4 -alkoxy) carbonyl- (Cχ-C 4 -alkoxy) carbonyl-Cχ-C-alkyl, carboxyl- (Cχ-C 4 ~ alkoxy) carbonyl-Cχ-C 4 -alkyl, -CH (R 9 ) -C (COOR 10 ) = N-OR 14 , - CH (R 9 ) -CO-N [CH (R 9 ) -COOR 10 ] -OR 14 , -CH (R 9 ) -C [-OCH (R 9 ) -COOR 10 ] = N-OR 14 ; R 9 , R 10 independently of one another are hydrogen or Cχ-Cg-alkyl;
R1:,R12 unabhängig voneinander Wasserstoff, Cχ-Cg-Alkyl,R 1 :, R 12 independently of one another hydrogen, Cχ-Cg-alkyl,
Carboxyl-Cχ-C4-alkyl oder (Cχ-C4-Alkoxy) carbonyl-Cχ-C4~ alkyl ;Carboxyl-Cχ-C 4 alkyl or (Cχ-C 4 alkoxy) carbonyl-Cχ-C 4 ~ alkyl;
R14 Cx-C -Alkyl;R 14 Cx-C alkyl;
R20 Chlor oder Brom;R 20 chlorine or bromine;
R21 Wasserstoff oder Chlor.R 21 is hydrogen or chlorine.
5. Substituierte Pyridazinone der Formel I nach Anspruch 1, wobei die Substituenten folgende Bedeutungen haben:5. Substituted pyridazinones of formula I according to claim 1, wherein the substituents have the following meanings:
R1 Amino ;R 1 amino;
R2 C -C6-Alkylthio, Cχ-Cg-Alkylsulfinyl oder Cχ-Cg-Alkyl- sulfonyl;R 2 C -C 6 alkylthio, Cχ-Cg-alkylsulfinyl or Cχ-Cg-alkylsulfonyl;
R3_R6 Wasserstoff; R 3_ R 6 hydrogen;
R7 Wasserstoff, Carboxyl, (Cχ-Cg-Alkoxy) carbonyl ,R 7 is hydrogen, carboxyl, (Cχ-Cg-alkoxy) carbonyl,
(Cχ-Cg-Alkoxy) carbonyl- (Cχ-Cg-alkoxy) carbonyl oder Cχ-Cg-Alkoxy;(Cχ-Cg-alkoxy) carbonyl- (Cχ-Cg-alkoxy) carbonyl or Cχ-Cg-alkoxy;
R8 Nitro;R 8 nitro;
R20,R21 unabhängig voneinander Wasserstoff, Chlor oder Brom.R 20 , R 21 independently of one another are hydrogen, chlorine or bromine.
6. Verfahren zur Herstellung von substituierten Benzylpyridazi - nonen der Formel I gemäß Anspruch 1, wobei R4 und R5 Wasserstoff bedeuten, dadurch gekennzeichnet, daß ein substituiertes Pyridazinon der Formel II6. A process for the preparation of substituted benzylpyridaziones of the formula I according to claim 1, where R 4 and R 5 are hydrogen, characterized in that a substituted pyridazinone of the formula II
Figure imgf000060_0001
Figure imgf000060_0001
mit einem substituierten Benzylhalogenid bzw. Benzylmesylat der Formel lila bzw. Illb III a: X = Halogen Illb: X = 0-S02-CH3 with a substituted benzyl halide or benzyl mesylate of the formula purple or Illb III a: X = halogen Illb: X = 0-S0 2 -CH 3
Figure imgf000061_0001
in Gegenwart einer Base umgesetzt wird.
Figure imgf000061_0001
is implemented in the presence of a base.
Verfahren zur Herstellung von substituierten Pyridazinonen der Formel I gemäß Anspruch 1, wobei C(R ,R5) für die Carbonylgruppe steht, dadurch gekennzeichnet, daß ein substituiertes Pyridazinon der Formel IIA process for the preparation of substituted pyridazinones of formula I according to claim 1, wherein C (R, R 5 ) represents the carbonyl group, characterized in that a substituted pyridazinone of formula II
Figure imgf000061_0002
Figure imgf000061_0002
mit einem substituierten Benzoesäurechlorid der Formel IVwith a substituted benzoic acid chloride of the formula IV
Figure imgf000061_0003
in Gegenwart einer Base acyliert wird.
Figure imgf000061_0003
is acylated in the presence of a base.
Verwendung der substituierten Pyridazinone der Formel I und der landwirtschaftlich brauchbaren Salze von I, gemäß Anspruchwl, als Herbizide oder zur Desikkation/Defoliation von Pflanzen.Use of the substituted pyridazinones of the formula I and the agriculturally useful salts of I as claimed in claim l w, as herbicides or for the desiccation / defoliation of plants.
Herbizides Mittel, enthaltend eine herbizid wirksame Menge mindestens eines substituierten Pyridazinons der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I, gemäß Anspruch 1, und mindestens einen inerten flüssigen und/oder festen Trägerstoff sowie gewünschtenfalls mindestens einen oberflächenaktiven Stoff. A herbicidal composition comprising a herbicidally effective amount of at least one substituted pyridazinone of the formula I or an agriculturally useful salt of I, as claimed in claim 1, and at least one inert liquid and / or solid carrier and, if desired, at least one surfactant.
10. Mittel zur Desikkation und/oder Defoliation von Pflanzen, enthaltend eine desikkant und/oder defoliant wirksame Menge mindestens eines substituierten Pyridazinons der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I, gemäß Anspruch 1, und mindestens einen inerten flüssigen und/oder festen Trägerstoff sowie gewünschtenfalls mindestens einen oberflächenaktiven Stoff.10. Agent for the desiccation and / or defoliation of plants, containing a desiccant and / or defoliantly effective amount of at least one substituted pyridazinone of the formula I or an agriculturally useful salt of I, according to claim 1, and at least one inert liquid and / or solid carrier and, if desired, at least one surfactant.
11. Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines substituierten Pyridazinons der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I, gemäß Anspruch 1, auf Pflanzen, deren Lebensraum oder auf Saatgut einwirken läßt.11. A method for controlling undesirable plant growth, characterized in that a herbicidally effective amount of at least one substituted pyridazinone of the formula I or an agriculturally useful salt of I, according to claim 1, is allowed to act on plants, their habitat or on seeds.
12. Verfahren zur Desikkation und/oder Defoliation von Pflanzen, dadurch gekennzeichnet, daß man eine desikkant und/oder defoliant wirksame Menge mindestens eines substituierten Pyridazinons der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I, gemäß Anspruch 1, auf Pflanzen einwirken läßt.12. A method for the desiccation and / or defoliation of plants, characterized in that a desiccant and / or defoliantly effective amount of at least one substituted pyridazinone of the formula I or an agriculturally useful salt of I, according to claim 1, is allowed to act on plants.
13. Verfahren nach Anspruch 12, dadurch gekennzeichnet, daß man Baumwolle behandelt. 13. The method according to claim 12, characterized in that cotton is treated.
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