WO1999018082A1 - Nouvelle pyridazinone substituee - Google Patents

Nouvelle pyridazinone substituee 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)
English (en)
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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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
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Abstract

L'invention concerne une pyridazinone substituée de formule (I) et ses sels où R1-R3 représentent H, NO¿2?, OH, halogène, alcoxy C1-C6, haloalcoxy C1-C6, SH, alkylthio C1-C6, haloalkylthio C1-C6, NH2, alkylamino C1-C6, Di(alkyl C1-C6)amino, CN, alkyle C1-C6, haloalkyle C1-C6, alkylsulfinyle C1-C6, haloalkylsulfinyle C1-C6, alkylsulfonyle C1-C6, haloalkylsulfonyle C1-C6, R?4, R5¿ représentent H ou, avec l'atome de carbone auquel ils sont liés, CO; R6 représente H, NO¿2?, halogène; R?7¿ représente H, NO¿2?, halogène, COOH, alcoxy C1-C6, alcoxy C1-C6-CO, alcoxy C1-C6-CO-(alcoxy C1-C6)-CO; R?8¿ représente H, NO¿2? ou OH éventuellement substitué, R?20¿ représente H, halogène si R8 = H ou NO¿2?; halogène si R?8¿ = OH éventuellement substitué; R21 représente de l'hydrogène ou de l'halogène. L'invention concerne également l'utilisation de cette substance comme herbicide pour la dessiccation/défoliation de plantes.
PCT/EP1998/006325 1997-10-07 1998-10-05 Nouvelle pyridazinone substituee WO1999018082A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6475955B2 (en) * 1998-03-26 2002-11-05 Sumitomo Chemical Company, Limited Pyridazinone derivatives

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1912770A1 (de) * 1969-03-13 1970-12-10 Basf Ag Pyridazonderivate
DE1966312A1 (de) * 1969-03-13 1972-03-09 Basf Ag Pyridazonderivate
EP0344684A2 (fr) * 1988-06-03 1989-12-06 Hoechst Aktiengesellschaft Dérivés de pyridazinone, procédé pour leur préparation, agent les contenant et leur utilisation en protection de plantes
EP0410238A2 (fr) * 1989-07-28 1991-01-30 Bayer Ag Dérivés de pyridazinone

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1912770A1 (de) * 1969-03-13 1970-12-10 Basf Ag Pyridazonderivate
DE1966312A1 (de) * 1969-03-13 1972-03-09 Basf Ag Pyridazonderivate
EP0344684A2 (fr) * 1988-06-03 1989-12-06 Hoechst Aktiengesellschaft Dérivés de pyridazinone, procédé pour leur préparation, agent les contenant et leur utilisation en protection de plantes
EP0410238A2 (fr) * 1989-07-28 1991-01-30 Bayer Ag Dérivés de pyridazinone

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEM. ZVESTI, vol. 38, no. 2, 1984, CZECH., pages 239 - 246 *
CHEMICAL ABSTRACTS, vol. 101, no. 28, 1984, Columbus, Ohio, US; abstract no. 110848u, KONECNY,V. ET AL.: "SYNTHESIS AND PESTICIDAL ACTIVITY OF 4,5-DICHLORO-2R-3-OXO-2H-PYRIDAZINES." page 651; XP002093390 *
CHEMICAL ABSTRACTS, vol. 95, no. 28, 1981, Columbus, Ohio, US; abstract no. 7312y, page 695; XP002093389 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6475955B2 (en) * 1998-03-26 2002-11-05 Sumitomo Chemical Company, Limited Pyridazinone derivatives

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