Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
  • C07C59/40—Unsaturated compounds
  • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
  • C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
  • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
  • C07D211/98—Nitrogen atom
• • 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
  • C07D405/04—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 directly linked by a ring-member-to-ring-member bond

Definitions

• the present invention relates to N-aminopyridone derivatives of the formula I:
• R 1 -R 5 can be the same or different substituents:
• C 2 -C 4 alkenyl, C 2 -C 4 alkynyl where the carbon radicals can be unbranched or branched and can each carry one to five halogen atoms and / or one or two of the following groups: alkoxy, alkylthio, cyano, nitro; two adjacent radicals from R 1 to R 5 are part of a cyclic acetal with five ring members, it being possible for the ring carbon atom to be substituted by one or two halogen atoms; Z: -O-, -NR 20 -, a bond;
• R 6 , R 7 are each hydrogen or together form one
• R 9 , R 10 are each hydrogen or together form one
• R 8 is hydrogen, C 3 -C 6 cycloalkyl, ZCOR 17 , C 1 -C 4 alkyl,
• a 5-membered saturated, unsaturated or aromatic heterocycle with one to four nitrogen atoms or one to three nitrogen atoms and additionally one sulfur or oxygen atom in the ring which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano , Alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, ZCOR 17 ; a thienyl or furyl radical which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, ZCOR 17 ; a 6-membered saturated, unsaturated or aromatic heterocycle with one to four nitrogen atoms or one to three nitrogen atoms and additionally a sulfur or oxygen atom in the ring, which can carry one to three halogen atoms and / or one to three of the following
• R 12 is hydrogen, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl. R 11 , R 12 together form a double bond which can be substituted by two identical or different substituents R 14 ;
• R 23 and R 24 may be substituted
• R 11 , R 12 form a nitro group with the neighboring N atom
• R 11 , R 12 are part of a nitrogen-bound, 5- or
• 6-membered saturated, unsaturated or aromatic heterocycle with one to four nitrogen atoms or one to three nitrogen atoms and additionally one sulfur or oxygen atom in the ring, which can carry one to three halogen atoms and / or one to three of the following radicals: oxo, nitro, Cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy;
• X O, S, NR 20 , R 13 C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, where the carbon radicals can be unbranched or branched and in each case one to five halogen atoms and / or one or two of the following groups can wear: alkoxy, alkylthio, cyano, nitro; R 14 is hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkynyl,
• C 2 -C 6 alkenyl where the carbon radicals can be unbranched or branched and can each carry one to five halogen atoms and / or one or two of the following groups: OH, C 1 -C 4 alkoxy, C 1 -C 4 - Alkoxyalkyl, alkylthio, cyano, substituted or unsubstituted phenyl, nitro, ZCOR 17 ;
• Phenyl which is unsubstituted or can carry one to five of the following substituents: halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 Alkoxy alkyl, C 1 -C 4 alkylamino, C 1 -C 4 dialkylamino, where the alkyl radicals can be unbranched or branched, OCN, SCN, OH, (CH 2 ) m SO n R 16 , NSO n R 13 , OSO n R 13 , ZCOR 17 , SF 5 ; a 5-membered saturated, unsaturated or aromatic heterocycle with one to four nitrogen atoms or one to three nitrogen atoms and an additional one Sulfur or oxygen atom in the ring, which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano, alky
• R 15 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyl,
• C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkylaminocarbonyl, where the carbon radicals can be unbranched or branched and can each carry one to five halogen atoms and / or one or two of the following groups: cyano, nitro;
• R 16 is hydroxy, amino, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl amino, C 1 -C 4 dialkylamino, where the carbon radicals can be unbranched or branched and in each case can carry one to five halogen atoms and / or one to two of the following groups: cyano, nitro; R 17 is hydrogen, amino, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkyl,
• Phenyl which is unsubstituted or can carry one to five of the following substituents: halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 -Alkoxy-alkyl, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, where the alkyl radicals can be unbranched or branched, OCN, SCN, OH, ZCOR 17 ;
• Phenoxy which can carry one to five of the following substituents: halogen, nitro, cyano, C 1 -C 4 -alkyl,
• alkyl radicals can be unbranched or branched, OCN, SCN, OH, ZCOR 17 , SF 5 ; Hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkynyl, C 2 -C 6 alkenyl, C 1 -C 6 alkylamino,
• C 1 -C 6 dialkylamino where the carbon radicals can be unbranched or branched and can each carry one to five halogen atoms and / or one or two of the following groups: C 1 -C 4 alkoxy, alkylthio, cyano, nitro, C 1 -C 4 alkylamino, OCN, SCN, OH, (CH 2 ) m SO n R 16 ,
• Phenyl which is unsubstituted or can carry one to five of the following substituents: halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 -Alkoxy-alkyl, C 1 -C 4 -alkoxyalkyloxy, C 1 -C 4 -alkylamino,
• alkyl radicals can be unbranched or branched, OCN, SCN, OH, (CH 2 ) m SO n R 16 , NSO n R 13 ' OSO n R 13 , ZCOR 17 , SF 5 ;
• Phenoxy which can carry one to five of the following substituents: halogen, nitro, cyano, C 1 -C 4 -alkyl,
• Sulfur or oxygen atom in the ring which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, ZCOR 17 ; a thienyl or furyl radical which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, ZCOR 17 ; a 6-membered saturated, unsaturated or aromatic heterocycle with one to four nitrogen atoms in the ring, which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, ZCOR 17 ; R 19 C 1 -
• Phenyl which is unsubstituted or can carry one to five of the following substituents: halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 -Alkoxy-alkyl, C 1 -C 4 -alkoxyalkyloxy, C 1 -C 4 -alkylamino,
• C 1 -C 4 dialkylamino where the carbon radicals can be unbranched or branched, OCN, SCN, OH, (CH 2 ) m SO n R 16 , NSO n R 13 , OSO n R 13 , ZCOR 17 , SF 5 ;
• Phenyl which carries a condensed five- or six-membered ring with optionally one or two heteroatoms such as nitrogen, sulfur or oxygen, the carbon atoms of which may optionally be halogen-substituted; Phenoxy which can carry one to five of the following substituents: halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxyalkyl, C 1 -C 4 alkoxyalkyloxy, C 1 -C 4 alkylamino, C 1 -C 4 dialkylamino, where the alkyl radicals can be unbranched or branched, OCN, SCN, OH, (CH 2 ) m SO n R 16 , NSO n R 13 , OSO n R 13 ,
• ZCOR 17 , SF 5 a 5-membered saturated, unsaturated or aromatic heterocycle with one to four nitrogen atoms or one to three nitrogen atoms and an additional one
• Sulfur or oxygen atom in the ring which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy; a thienyl or furyl radical which can carry one to three halogen atoms and / or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy;
• R 20 is hydrogen, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, where the carbon radicals can be unbranched or branched and can each carry one to five halogen atoms and / or one or two of the following groups: alkoxy, cyano,
• R 21 , R 22 part of a cyclic acetal or thioacetal with five or six ring members; C 1 -C 4 alkoxy, which can be unsubstituted or can carry one to five of the following radicals: cyano, nitro, halogen;
• R 23 , R 24 are part of a cyclic system with five to six ring members, which can be unsubstituted or can carry one to five of the following radicals: NO 2 , CN, halogen, OCN,
• the object of the present invention was to find new N-substituted arylpyridones with improved properties and a process for their preparation.
• the new compounds of the formula Ib are obtained, for example, by dehydrogenating compounds of the formula Ia with DDQ
• the reaction solution is stirred at a temperature of 50-150 ° C., in particular at 110 ° C., until the reaction has ended.
• the mixture is worked up by filtering through Alox n III.
• the new compounds of the formula Ia are obtained by reacting 6-aryl-2H-dihydro- ⁇ -pyrones of the general formula II with hydrazine / hydrazide hydrochlorides.
• the substituents R 1 -R 5 , R 8 and R 11 -R 12 have the meaning given at the outset.
• the reaction is carried out by adding a hydrazine / hydrazide to a solution of a dihydropyrone II in the presence of an auxiliary base.
• a hydrazine / hydrazide for complete conversion of the dihydropyrone II, it is expedient to add at least a double excess of hydrazide / hydrazine and an excess of auxiliary base.
• Tertiary alkyl amines or pyridine are suitable as auxiliary bases. Methylene chloride, dichloroethane or diethyl ether can be used as the solvent.
• reaction solution After the reaction solution has been stirred overnight, the work-up is carried out by shaking out with aqueous HCl and aqueous NaHC0 3 solution. The residue obtained after evaporation of the solvent is taken up in toluene, catalytic amounts of PTSS (p-toluenesulfonic acid) are added and the mixture is boiled under reflux in a water separator. After complete conversion, the reaction solution is worked up by partitioning between ether and dilute NaHCO 3 solution.
• PTSS p-toluenesulfonic acid
• 6-Aryl-3, 4-2H-dihydro- ⁇ -pyrones of structure IIc with cyclopropyl ring in the 4-position (R 8 cyclo C 3 H 5 ) are accessible from
• 6-Aryl- ⁇ -pyrones of the structure Ha are also accessible by acid-induced cyclization of 5-aryl-3-hydroxypent-4-acid esters, which in turn are obtained by Reformatzki reaction of arylacetylene methyl ketones with ⁇ -bromocarboxylic acid esters (see Arch. Pharm. 1961, 294, 234 - 239, see Route 3,
• 6-aryl- ⁇ -pyrones of structure IIc is the cyclocondensation of ⁇ - ⁇ -unsaturated- ⁇ -keto esters, which in turn by reaction of ⁇ -silyl- ⁇ , ⁇ -unsaturated esters Aryl carboxylic acid chlorides are shown (see J. Org. Chem, 1983, 48, 5288 - 5302, see Route 4, Scheme 4).
• R 1 can be:
• Halogen such as fluorine, bromine, chlorine, iodine, particularly preferably fluorine and chlorine;
• C 1 -C alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl;
• C 1 -C 4 -alkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 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, pentafluoroethyl and 3-chloropropyl, preferably trifluoromethyl; C 1 -C 4 alkoxy-C 1 -C 4 alkyl such as methoxymethyl, ethoxymethyl,
• C 1 -C 4 alkoxy-C 1 -C alkyl such as methoxymethyl, ethoxymethyl, 2-methoxyethyl and 2-ethoxyethyl;
• NC 1 -C 4 alkylamino such as N-methylamino, N-ethylamino, N-propylamino, N-1-methylethylamino, N-butylamino, N-1-methylpropylamino,
• Sulfonic acid, sulfonamide, C 1 -C 4 alkylthio such as methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio and 1, 1-dimethylethylthio, especially methylthio;
• C 1 -C 4 alkylthioethyl such as methylthioethyl, ethylpropylthioethyl, n-propylthioethyl, 1-methylethylthioethyl, n-butylthioethyl, 1-methylpropylthioethyl, 2-methylpropylthioethyl and 1,1-dimethylthioethyl, especially methylthioethyl;
• C 1 -C 4 alkylthiomethyl such as methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, 1-methylethylthiomethyl, n-butylthiomethyl, 1-methylpropylthiomethyl, 2-methylpropylthiomethyl and 1,1-dimethylethylthiomethyl, especially methylthiomethyl;
• C 1 -C 4 haloalkylthio such as chloromethylthio, dichloro
• C 1 -C 4 haloalkylthiomethyl such as chloromethylthiomethyl, dichloromethylthiomethyl, trichloromethylthiomethyl, fluoromethylthiomethyl, difluoromethylthiomethyl, trifluoromethylthiomethyl, chlorofluoromethylthiomethyl, chlorodifluoromethylthiomethylomethyl, 1methylthiomethyl, 1
• 2,2,2-trifluoroethylthiomethyl 2-chloro-2,2-difluoroethylthiomethyl, 2,2-dichloro-2 fluoroethylthiomethyl, 2,2,2-trichloroethylthiomethyl and pentafluoroethylthiomethyl, especially trifluoromethylthiomethyl.
• C 1 -C 4 -Halogenalkylthioethyl as Chlormethylthioethyl, Dichlormethylthioethyl, Trichlormethylthioethyl, Fluormethylthioethyl, Difluormethylthioethyl, Trifluormethylthioethyl, Chlorfluormethyl- thioethyl, Chlordifluormethylthioethyl, 1-Fluorethylthioethyl, 2-Fluorethylthioethyl, 2,2-Difluorethylthioethyl, 2,2, 2-Trifluorethylthioethyl, 2- Chloro-2,2-difluoroethylthioethyl,
• Hydroxysulfonyl-C 1 -C 4 alkyl such as hydroxysulfonylmethyl, hydroxysulfonylethyl, hydroxysulfonylpropyl, hydroxysulfonylbutyl, in particular hydroxysulfonylmethyl; C 1 -C 4 alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl and 1, 1-dimethylethylsulfinyl, especially methylsulfinyl; C 1 -C 4 alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, n-propylsulfony
• Di-C 1 -C 4 alkylsulfamoyl such as dimethylsulfamoyl, diethylsulfamoyl, dipropylsulfamoyl, N-methyl-N-ethylsulfamoyl, N-methyl-N-propylsulfamoyl, N-methyl-N-1-methylethylsulfamoyl, N-methyl-N- 1, 1-dimethylethylsulfamoyl, N-ethyl-N-1-methylethylsulfamoyl and N-ethyl-N-1, 1-dimethylethylsulfamoyl; especially dimethylsulfamoyl,
• Di-C 1 -C 4 alkylsulfinamoyl such as dimethylsulfinamoyl, diethylsulfinamoyl, dipropylsulfinamoyl, dibutylsulfinamoyl, N-methyl-N-ethylsulfinamoyl, N-methyl-N-propylsulfinamoyl, N-methyl-N-1-methyloyl Methyl-N-1,1-dimethylethylsulfinamoyl, N-ethyl-N-1-methylethylsulfinamoyl and N-ethyl-N-1, 1-dimethylethylsulfinamoyl; especially dimethylsulfinamoyl.
• the group OSO n R 13 defined above stands for example for: C 1 -C 4 alkylsulfinyloxy such as methylsulfinyloxy, ethylsulfinyloxy, n-propylsulfinyloxy, 1-methylethylsulfinyloxy, n-butylsulfinyloxy, 1-methylpropylsulfinyloxy, 2-methylpropylsulfinyloxy and 1,1-dimethylethylsulfinyloxy, especially methylsulfinyloxy; C 1 -C 4 alkylsulfonyloxy such as methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1-methylethylsulfonyloxy, n-butylsulfonyloxy, 1-methylpropylsulfonyloxy, 2-methylpropyl
• Chlorodifluoromethylsulfonyloxy 1-fluoroethylsulfonyloxy, 2-fluoroethylsulfonyloxy, 2, 2-difluoroethylsulfonyloxy, 2,2,2-trifluoroethylsulfonyloxy, 2-chloro-2-fluoroethylsulfonyloxy,
• the group NR 20 SO n R 13 defined above represents, for example: C 1 -C 4 alkylsulfinylamino such as methylsulfinylamino, ethylsulfinylamino, n-propylsulfinylamino, 1-methylethylsulfinylamino, n-butylsulfinylamino, 1-methylpropylsulfinylamino, 2-methylpropylsulfinylamino Dimethylethylsulfinylamino, in particular methylsulfinylamino; C 1 -C 4 alkylsulfonylamino such as methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, 1-methylethylsulfonylamino, n-butylsulfonylamino, 1-methylpropy
• NC 1 -C 4 alkylsulfinyl-N-methyl-amino such as N-methylsulfinyl-N-methyl-amino, N-ethylsulfinyl-N-methyl-amino, Nn-propylsulfinyl-N-methyl-amino, N-1- Methylethylsulfinyl-N-methyl-amino, Nn-butylsulfinyl-N-methyl-amino, N-1-methylpropylsulfinyl-N-methyl-amino, N-2-methylpropylsulfinyl-N-methyl-amino and N-1, 1- Dimethylethylsulfinyl-N-methyl-amino, especially N-methylsulfinyl-N-methyl-amino; NC 1 -C 4 alkylsulfinyl-N-ethylamino such as N-methylsulfinyl
• NC 1 -C 4 alkylsulfonyl-N-methyl-amino such as N-methylsulfonyl-N-methyl-amino, N-ethylsulfonyl-N-methyl-amino, Nn-propylsulfonyl-N-methyl-amino, N-1-methylethylsulfonyl- N-methyl-amino, Nn-butylsulfonyl-N-methyl-amino, N-1-methylpropylsulfonyl-N-methyl-amino, N-2-methylpropylsulfonyl-N-methyl-amino and N-1, 1-dimethylethylsulfonyl- N-methylamino, especially N-methylsulfonyl-N-methylamino;
• NC 1 -C 4 alkylsulfonyl-N-ethylamino such as N-methylsulfonyl-N-ethylamino, N-ethylsulfonyl-N-ethylamino, Nn-propylsulfonyl-N-ethylamino, N-1-methylethylsulfonyl- N-ethyl-amino, Nn-butylsulfonyl-N-ethyl-amino, N-1-methylpropylsulfonyl-N-ethyl-amino, N-2-methylpropylsulfonyl-N-ethyl-amino and N-1, 1-dimethylethylsulfonyl- N-ethyl-amino, especially N-methylsulfonyl-N-ethyl-amino;
• the group OR 15 defined above stands for example for: hydroxy; C 1 -C 4 alkoxy such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy, especially methoxy and ethoxy; partially or fully halogenated C 1 -C 4 alkoxy such as chloromethyloxy, dichloromethyloxy, trichloromethyloxy, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy,
• Dichlorofluoromethyloxy chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, 1,1-difluoro-2,2-difluoroethyloxy, 2-chloro-2-fluoroethyloxy,
• C 1 -C 2 haloalkoxy such as trifluoromethoxy, difluoromethyloxy
• NC 1 -C 4 alkylcarbamoyl such as N-methylcarbamoyl, N-ethylcarbamoyl, Nn-propylcarbamoyl, N-1-methylethylcarbamoyl, Nn-butylcarbamoyl, N-1-methylpropylcarbamoyl, N-2-methylpropylcarbamoyl and N-1, 1- Dimethylethylcarbamoyl, especially N-methylcarbamoyl; Di-C 1 -C 4 alkylcarbamoyl such as dimethylcarbamoyl, diethylcarbamoyl, dipropylcarbamoyl, dibutylcarbamoyl, N-methyl-N-ethylcarbamoyl, N-methyl-N-propylcarbamoyl, N-methyl-N-1-methylethylcarbamoyl, N-methyl-
• C 1 -C 4 alkylcarbonyloxy such as methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy and 1,1-dimethylethylcarbonyloxy, especially methylcarbonyloxy;
• C 1 -C 2 haloalkylcarbonyloxy such as chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, Chlorfluoracetyl, Dichlorfluoracetyl, Chlordifluoracetyl, alpha- Fluorpropionyl, beta-Fluorpropionyl, beta, beta-Difluorpropionyl, beta, beta, beta-trifluoropropion
• the group ZCOR 17 defined above stands for example for: C 1 -C 4 alkylcarbonyl such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl and 1,1- Dimethylethylcarbonyl, especially methylcarbonyl;
• C 1 -C 4 alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylprooxycarbonyl, 2-methylpropoxycarbonyl and 1,1-dimethylethoxycarbonyl, especially methoxycarbonyl;
• C 1 -C 4 alkylcarbonylamino such as methylcarbonylamino, ethylcarbonylamino, n-propylcarbonylamino, 1-methylethylcarbonylamino, n-butylcarbonylamino, 1-methylpropylcarbonylamino, 2-methylpropylcarbonylamino and 1,1-dimethylethylcarbonylamino, in particular methylcarbonylamino;
• C 1 -C 4 -alkylcarbonyl-N-methyl-amino such as N-methylcarbonyl-N-methyl-amino, N-ethylcarbonyl-N-methyl-amino, Nn-propylcarbonyl-N-methyl-amino, N-1- Methylethylcarbonyl-N-methyl-amino, Nn-butylcarbonyl-N-methyl-amino, N-1-methylpropylcarbonyl-N-methyl-amino, N-2-methylpropylcarbonyl-N-methyl-amino and N-1, 1- Dimethylethyl carbonyl-N-methylamino, especially N-methylcarbonyl-N-methylamino;
• NC 1 -C 4 alkylaminocarbonylamino such as N-methylaminocarbonylamino, N-ethylaminocarbonylamino, Nn-propylaminocarbonylamino, N-1-methylethylaminocarbonylamino, Nn-butylaminocarbonylamino, N-1-methylpropylaminocarbonylamino, N-2-methylproylaminoamino, N-2-methylproylaminoaminoamin especially methylaminocarbonylamino;
• NC 1 -C 4 alkylaminocarbonyl-N-methylamino such as N-methylaminocarbonyl-N-methylamino, N-ethylaminocarbonyl-N-methylamino, Nn-propylaminocarbonyl-N-methylamino, N-1- Methylethylaminocarbonyl-N-methyl-amino, Nn-butylaminocarbonyl-N-methyl-amino, N-1-methylpropylaminocarbonyl-N-methyl-amino, N-2-methylpropylaminocarbonyl-N-methyl-amino and N-1,1-dimethylethylaminocarbonyl- N-methylamino, especially N-methylaminocarbonyl-N-methylamino; N, N-di-C 1 -C 4 -alkylaminocarbonylamino such as N, N-dimethylaminocarbonylamino, N, N-
• C 1 -C 4 alkyl carbonate such as methyl carbonate, ethyl carbonate, propyl carbonate, 1-methyl ethyl carbonate, butyl, 1-methyl propyl carbonate, 2-methyl propyl carbonate, 1,1-dimethyl ethyl carbonate; all carbon radicals of the groups defined above can optionally be replaced by one to five halogen atoms such as fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine, C 1 -C 4 alkoxy, preferably methoxy and ethoxy, C 1 -C 4 alkylthio, preferably methylthio and ethylthio, cyano, nitro or phenyl;
• R 2 can be a substituent mentioned under R 1 , identical or different from R 1 ;
• R 3 can be a substituent mentioned under R 1 , identical or different from R 1 ;
• R 4 can be a substituent mentioned under R 1 , identical or different from R 1 ;
• R 5 can be a substituent mentioned under R 1 , identical or different from R 1 ; two adjacent radicals R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5, preferably R 1 and R 2 form a cyclic, five-membered acetal / carbonate, the ring carbon atom being either a double bond Can carry oxygen, two bromine, two chlorine or two fluorine atoms, preferably two fluorine atoms; R 8 can be:
• C 3 -C 6 cycloalkyl such as cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
• R 11 can be:
• C 1 -C 4 alkyl as defined above for R 1 ; partially or fully halogenated C 1 -C 4 alkyl as defined under R 1 ; C 2 -C 4 alkenyl as defined above for R 1 ;
• 2,4-difluorophenylsulfonyl 2 ', 2'-difluoro-4, 5-benzo-dioxolane-3-sulfonyl, 3-trifluoromethylphenylsulfonyl; substituted phenylsulfinyl such as 2, 4-difluorophenylsulfinyl, 2,4-dichlorophenylsulfinyl, 2 ', 2'-difluoro-4, 5-benzodioxolane-3-sulfinyl, 3-trifluoromethylphenylsulfinyl, 3-fluorophenylsulfinyl, 3-chlorophenylsulfinyl,
• 2,4-difluorophenylsulfinyl 2 ', 2'-difluoro-4, 5-benzo-dioxolane-3-sulfinyl, 3-trifluoromethylphenylsulfinyl; substituted phenyl such as 2,4-difluorophenyl, 2,4-dichlorophenyl, 2 ', 2'-difluoro-4, 5-benzodioxolan-3-yl-, 3-trifluoromethylphenyl, 3-fluorophenyl, 3-chlorophenyl, 2-cyano- 4-fluorophenyl,
• R 18 can be:
• C 1 -C 6 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,
• Dichlorofluoromethyloxy chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, 2-chloro-2-fluoroethyloxy, 2-chloro-2,2-difluoroethyloxy,
• C1-C 2 _haloalkoxy such as trifluoromethoxy
• C 2 -C 6 alkenyl such as 2-propenyl, 2-butenyl, 3-butenyl
• C 2 -C 6 alkynyl such as propargyl, 2-butynyl, 3-butynyl, 2-pentynyl,
• 3-pentynyl 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,
• C 3 -C 6 cycloalkyl such as cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
• cyclopropyl 1-methylcyclopropyl; partially or fully halogenated C 1 -C 4 alkyl as defined for R 1 ;
• C 1 -C 4 alkoxy-C 1 -C 2 alkyl such as methoxymethyl, ethoxymethyl, n-propoxymethyl, (1-methylethoxy) methyl, n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy ) methyl, (1,1-dimethylethoxy) methyl, methoxyethyl, ethoxyethyl, n-propoxyethyl,
• Cyano- (C 1 -C 6 ) -alkyl such as cyanomethyl, 1-cyanoeth-1-yl, 2-cyano-noeth-1-yl, 1-cyano-prop-1-yl, 2-cyano-prop-1- yl, 3-cyano-prop-1-yl, 1-cyano-prop-2-yl, 2-cyano-prop-2-yl, 1-cyano-but-1-yl, 2-cyano-but-1- yl, 3-cyano-but-1-yl, 4-cyano-but-1-yl, 1-cyano-but-2-yl, 2-cyano-but-2-yl, 1-cyano-but-3- yl, 2-cyano-but-3-yl, 1-cyano-2-methyl-prop-3-yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop- 3-yl, and 2-cyanomethyl-prop-2-yl, preferably cyanomethyl, 2-cyanoeth-1-yl; NC 1 -C
• N, N-Di-C 1 -C 4 alkylamino such as N, N-dimethylamino, N, N-diethylamino, N, N-dipropylamino, N, N-dibutylamino, N-methyl-N-ethylamino, N-Me- ethyl-N-propylamino, N-methyl-N-1-methylethylamino, N-methyl-N-1,1-dimethylethylamino, di-1-methylethylamino, N-ethyl-N-1-methylethylamino and N-ethyl- N-1, 1-dimethylethylamino, especially dimethylamino, N, N-diethylamino;
• R 11 would then preferably be: thioformyl
• R 11 would then preferably be: 1-iminomethyl, 1-iminoethyl, 1-imino-2-methylpropyl;
• haloalkoxyiminomethyl such as 1-trifluoromethoxy-1-imino-methyl; - 1-Imino-2-methyl-2-propenyl, 1-imino-2-methyl-2-butenyl, 1-imino-2, 3-dimethyl-2-propenyl and
• R 11 can optionally also have a group CXR 18
• R 11 would then preferably be: - methyliminomethyl, 1-methyliminoethyl, 1-methylimino-2-methylpropyl, ethyliminomethyl, 1-ethyliminoethyl, l-ethylimino-2-methylpropyl, (1-methylethyl) iminomethyl, 1- (1-methylethyl ) iminoethyl, 1- (1-methylethyl) imino-2-methylpropyl;
• R 11 optionally by one to five halogen atoms such as fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine, C 1 -C 4 alkoxy as mentioned under R 1 , preferably methoxy and ethoxy, C 1 -C 4 -Alkylthio as mentioned under R 1 , preferably methylthio and ethylthio, cyano, nitro, C 1 -C 4 -alkylamino as mentioned under R 1 , cyanato, thiocyanato, OR 15 as defined above, (CH 2 ) m SO n R 16 as defined above, NSO n R 13 as defined above, O
• R 11 can also be: a 5- or 6-membered heterocyclic, saturated or unsaturated ring containing one to four heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen, for example five-ring heteroaromatics such as 2-furyl, 3-furyl, 2 -Thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl , 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4 -Oxadiazol-5-yl,
• Heterocycles containing one to three nitrogen atoms and / or one or two oxygen or sulfur atoms such as 2-tetrahydro- furanyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dithiolan-2-yl, 1,3-dithiol 4-yl, 1-3-dithian-2-yl, 1,3-dithian-4-yl, 5,6-dihydro-4H-1,3-thiazin-2-yl, 1,3-oxathiolan-2- yl, 1,3-oxathian-2-yl,
• a group -ZCOR 17 for example alkylcarbonyl as mentioned above, alkoxycarbonyl as mentioned above, N-alkylcarbamoyl as mentioned above, dialkylcarbamoyl as mentioned above;
• C 1 -C 4 haloalkyl such as, for example, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2,2, 2-trifluoroethyl,
• C 1 -C 4 haloalkoxy such as, for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy,
• a double-bonded oxygen which may optionally also be present in the tautomeric form as a hydroxy group, for example thiazolin-4, 5-dion-2-yl, 3-oxo-3H-1,2,4-di-thiazolyl or 2-oxo -2H-1,3,4-dithiazolyl;
• 2,1,3-benzothiadiazolyl benzotriazolyl, benzofuroxanyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl or phthalazinyl;
• R 11 can also be:
• C 3 -C 6 cycloalkyl as defined above, optionally with one to four halogen atoms, fluorine, chlorine, bromine, iodine or
• C 1 -C 4 alkoxy may be substituted as defined under R 1 ;
• Phenoxy which is unsubstituted or can carry one to five of the following substituents: fluorine, chlorine, bromine, iodine, nitro, cyano, C 1 -C 4 alkyl as defined under R 1 , C 1 -C 4 haloalkyl as under R 1 defined, C 1 -C 4 alkylamino as defined under R 1 , C 1 -C 4 dialkylamino as defined under R 1 , OCN, OR 15 as defined under R 1 , SF 5 , SCN, (CH 2 ) m SO n R 16 as defined under R 1 , NSO n R 13 as defined under R 1 , OSO n R 13 as defined under R 1 , ZCOR 17 as defined under R 1 ; a 5- or 6-membered heterocyclic, saturated or unsaturated radical containing one to three heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen, for example five-membered heteroaromatics such as 2-furyl, 3-furyl
• Heterocycles containing one to three nitrogen atoms and / or one or two oxygen or sulfur atoms such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, tetrahydrothiopyran-2-yl, tetrahydrothiopyranethan-3-yl 4-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 1-3-dithian-2-yl, 1,3-dithian-4-yl, 5,6-dihydro- 4H-1,3-thiazin-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl,
• a group -ZCOR 17 for example alkylcarbonyl as mentioned above, alkoxycarbonyl as mentioned above, N-alkylcarbamoyl as mentioned above, dialkylcarbamoyl as mentioned above;
• C 1 -C 4 haloalkyl such as, for example, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2,2, 2-trifluoroethyl,
• C 1 -C 4 haloalkoxy such as, for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy,
• a double-bonded oxygen which may optionally also be present in the tautomeric form as a hydroxy group, for example thiazolin-4, 5-dion-2-yl, 3-oxo-3H-1,2,4-di-thiazolyl or 2-oxo -2H-1,3,4-dithiazolyl;
• R 11 can also be: a C 1 -C 4 alkyl defined above, which a) is substituted with a 5- or 6-membered cyclic (thio) acetal, preferably dioxolan-2-yl;
• R 12 can be:
• R 11 and R 12 can optionally also form a double bond which can be substituted by two identical or different of the following substituents R 14 :
• R 14 hydrogen
• C 1 -C 6 alkenyl as defined under R 18 where all defined carbon radicals optionally by one to five halogen atoms such as fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine, C 1 -C 4 alkoxy as mentioned under R 1 , preferably methoxy and ethoxy, C 1 -C 4 alkylthio as mentioned under R 1 , preferably methylthio and ethylthio, cyano, nitro, substituted phenyl as defined above, OR 15 as defined above, ZCOR 17 as defined above can be substituted.
• halogen atoms such as fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine
• C 1 -C 4 alkoxy as mentioned under R 1
• methoxy and ethoxy preferably methoxy and ethoxy
• C 1 -C 4 alkylthio as mentioned under R 1
• cyano nitro, substituted phenyl as
• Phenyl or optionally substituted phenyl as defined above for R 11 a 5- or 6-membered heterocyclic, saturated or unsaturated ring containing one to four heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen, for example five-membered and six-membered heterocycles as described for R 5 .
• the Grignard complex produced is slowly added dropwise to a solution of 3.84 g (0.03 mol) of 3-methylglutaric anhydride in 80 ml of dry diethyl ether.
• the solution is heated under reflux for 4 h and then stirred overnight.
• the reaction solution is poured onto H 2 O and acidified to destroy the Grignard complex by adding HCl.
• the desired product is obtained by extracting three times with diethyl ether and then drying the org. Phases over Na 2 SO 4 .
• the compounds I or the herbicidal compositions comprising them and their environmentally compatible salts of, for example, alkali metals, alkaline earth metals or ammonia and amines or the herbicidal compositions comprising them can be used in crops such as wheat, rice, maize, Soybeans and cotton fight weeds and grass weeds very well without damaging crops, an effect that occurs above all at low application rates. Taking into account the versatility of the application methods, the compounds I or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants. Be considered
• napobrassica Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Cofea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis
• the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
• the herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active ingredients are less compatible for certain crop plants, application techniques can be used in which the active ingredients are less compatible for certain crop plants.
• 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 compounds get onto the leaves of unwanted plants growing below them or the uncovered soil (post-directed, lay-by).
• the compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring be used.
• directly sprayable aqueous solutions, powders, suspensions including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring be used.
• the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
• Inert additives include mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, methanol,
• 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 can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
• concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
• alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin-,
• Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
• Granules, e.g. B. coating, impregnation and homogeneous granules can be prepared by binding the active ingredients to solid carriers.
• Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate,
• Ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
• the formulations generally contain between 0.01 and 95% by weight, preferably between 0.5 and 90% by weight, of active ingredient.
• the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
• the compounds I according to the invention can be formulated, for example, as follows:
• Dissolved mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenyl and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil.
• III 20 parts by weight of active ingredient No. 1.159 are in a
• Dissolved mixture which consists of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction from the boiling point 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.
• aqueous dispersion which contains 0.02% by weight of the active ingredient.
• Parts by weight of the sodium salt of diisobutyl-naphthalene- ⁇ -sulfonic acid, 17 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel are mixed well and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight
• Water contains a spray mixture which contains 0.1% by weight of the active ingredient.
• V 3 parts by weight of active ingredient No. 1.159 are 97
• N-aminopyridone derivatives of the formula I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
• diazines for example, diazines
• the amount of active ingredient applied is 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.).
• 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.
• pre-emergence treatment the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
• the tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, unless this was affected by the active ingredients.
• the application rate for pre-emergence treatment is 0.5 or 0.25 kg / ha a.S.
• test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, are first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. The test plants are either sown directly and grown in the same containers, or they are first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
• the application rate for post-emergence treatment is 0.5 or 0.25 kg / ha a.S.
• the plants were kept at 10-25 ° C and 20-35 ° C depending on the species.
• the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.

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• 1995
  • 1995-05-22 DE DE19518739A patent/DE19518739A1/de not_active Withdrawn
• 1996
  • 1996-05-08 EP EP96919712A patent/EP0815083A1/de not_active Withdrawn
  • 1996-05-08 JP JP8535302A patent/JPH11511743A/ja active Pending
  • 1996-05-08 CA CA002218550A patent/CA2218550A1/en not_active Abandoned
  • 1996-05-08 AU AU58156/96A patent/AU5815696A/en not_active Abandoned
  • 1996-05-08 WO PCT/EP1996/001923 patent/WO1996037471A1/de not_active Application Discontinuation
  • 1996-05-08 US US08/952,251 patent/US6028033A/en not_active Expired - Fee Related
  • 1996-05-21 ZA ZA9604034A patent/ZA964034B/xx unknown
  • 1996-05-22 AR ARP960102669A patent/AR002075A1/es unknown

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