WO1994011344A1 - 3,4,5,6-tetrahydrophtalimides substitues utilises comme herbicides et/ou comme defoliants ou comme siccatifs - Google Patents

3,4,5,6-tetrahydrophtalimides substitues utilises comme herbicides et/ou comme defoliants ou comme siccatifs Download PDF

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WO1994011344A1
WO1994011344A1 PCT/EP1993/003039 EP9303039W WO9411344A1 WO 1994011344 A1 WO1994011344 A1 WO 1994011344A1 EP 9303039 W EP9303039 W EP 9303039W WO 9411344 A1 WO9411344 A1 WO 9411344A1
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ethyl
methyl
alkyl
formula
substituted
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PCT/EP1993/003039
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German (de)
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Elisabeth Heistracher
Gerhard Hamprecht
Ralf Klintz
Peter Schaefer
Uwe Kardorff
Karl-Otto Westphalen
Matthias Gerber
Helmut Walter
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Basf Aktiengesellschaft
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Priority to AU54633/94A priority Critical patent/AU5463394A/en
Publication of WO1994011344A1 publication Critical patent/WO1994011344A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton

Definitions

  • the present invention relates to new substituted 3, 4, 5, 6-tetrahydrophthaliird.de of the general formula I
  • R 1 is hydrogen or a Ci-C ⁇ -alkyl group
  • R 2 is hydrogen or halogen
  • R 3 is hydrogen, halogen, nitro, cyano, methyl, one to three times halogen-substituted methyl, methoxy, one to three times halogen-substituted methoxy;
  • R 6 is hydrogen or Ci-C ⁇ -alkyl
  • R 7 is hydrogen, Ci-C ⁇ -alkyl, C 3 -C 6 ⁇ alkenyl, C 3 -C 6 ⁇ alkynyl, C 3 -C G -cycloalkyl, Ci-C ⁇ -haloalkyl, C ⁇ -C 6 -cyanoalkyl, C ⁇ -C 6 -alkoxy-C 6 -alkyl, -C-C 6 -alkylthio-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxycarbonyl-Ci-C ß -alkyl, C ⁇ -C 6 -alkyloximino-C ⁇ - C 6 alkyl, di (-C 6 alkoxy) -C 2 -C 6 alkyl, di (C 6 -C 6 alkylthio) -C 2 -C 6 ⁇ alkyl, C 3 -C 6 Haloalkenyl,
  • R 7 is not methyl or ethyl if R 2 is hydrogen or fluorine and R 3 is chlorine and R 5 is chlorine or bromine and R 6 is hydrogen.
  • substituted 3, 4, 5, 6-tetrahydrophthalimides as herbicides (cf. DE-A 36 03 789; EP-A 300 398; earlier German application DE-A 42 13 715) or as desiccation and emission - Medium (cf. DE-A 39 05 916) can be used. However, their effects are not always completely satisfactory.
  • the object of the invention was therefore to find tetrahydrophthalimides with improved biological properties.
  • Halogen fluorine, chlorine, bromine, and iodine
  • C ⁇ -C 6 alkyl methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3rd -Methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,
  • R 1 is hydrogen or Ci-C ⁇ -alkyl, in particular hydrogen or -CC-alkyl, for example methyl, ethyl, isopropyl, tert-butyl;
  • R 2 is hydrogen or halogen, in particular hydrogen, fluorine, chlorine;
  • R 3 is hydrogen, halogen, nitro, cyano, methyl
  • R 5 halogen, especially chlorine and bromine
  • R 6 is hydrogen or -CC 6 alkyl, preferably hydrogen, methyl, ethyl
  • R 7 is hydrogen, -CC 6 alkyl
  • C 3 -C 6 alkenyl such as prop-1-en-l-yl, prop-2-en-l-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methyl-prop-1-en-l-yl, 2-methyl-p_rop-l-en-l-yl, 1-methyl-prop-2-en-l-yl, 2-methylprop-2-en-l-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl-but- 1-en-l-yl, 2-methylbut-l-en-l-yl, 3-methyl-but-l-en-l-yl, l-methyl-but-2-en-l-yl, 2- Methyl-but-2-en-l-yl, 3-methyl-but-2-en-l-yl, l-methyl-but
  • Cs-C ß- alkynyl such as prop-1-in-l-yl, prop-2-in-l-yl, 2-methyl-prop-2-in-l-yl, n-but-1-in-l -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, Pent-2-in-1-yl, Pent-2-in-4-yl, 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-hexl-in-5-yl
  • C 3 -C 6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;
  • haloalkyl for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-chloroethyl, 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, 3-fluoropropyl, 4-chlorobutyl, 4-fluorobutyl;
  • Ci-C ⁇ - cyanoalkyl for example cyanomethyl, 1-cyanoeth-l-yl, 2-cyano-eth-l-yl, 1-cyanoprop-l-yl, 2-cyano-prop-l-yl, 3-cyano- prop-1-yl, l-cyanoprop-2-yl, 2-cyano-prop-2-yl, 1-cyano-but-l-yl, 2-cyanobut-l-yl, 3-cyano-but-l- yl, 4-cyano-but-l-yl, l-cyano-but-2-yl, 2-cyano-but-2-yl, 1-cyano-but-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 and 2-cyanomethylprop-2-yl;
  • Ci-Ce-alkoxy-Ci-C ⁇ - alkyl e.g. methoxymethyl, ethoxymethyl, n-propoxymethyl, (l-methylethoxy) methyl, n-butoxymethyl, (l-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1, l-dimethylethoxy) methyl, n-pentoxymethyl, (1-methylbutoxy) methyl, (2-methylbutoxy) methyl, (3-methylbutoxy) methyl, (2,2-dimethylpropoxy) methyl, (1-ethylpropoxy) methyl, n-hexoxymethyl, (1, 1-dimethylpropoxy) methyl, (1,2-dimethylpropoxy) methyl, (1-methylpentoxy) methyl, (2-methylpentoxy) methyl, (3-methylpentoxy) methyl, ( 4-methylpen- toxy) methyl, (1,1-dimethylbutoxy) methyl, (1,2-dimethylbutoxy) methyl, (1,
  • C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl for example methylthiomethyl, ethylthio-methyl, n-propylthiomethyl, (1-methylethylthio) methyl, n-butylthiomethyl, (1-methylpropylthio) methyl, (2-methylpropyl- thio) methyl, (1,1-dimethylethylthio) methyl, n-pentylthiomethyl, (1-methylbutylthio) methyl, (2-methylbutylthio) methyl, (3-methylbutylthio) methyl, (2,2-dimethylpropylthio) methyl, ( 1-ethylpropylthio) methyl, n-hexylthiomethyl, (1, 1-dimethylpropylthio) methyl, (1,2-dimethylpropylthio) methyl, (1-methylpentylthio) methyl, (2-methylp
  • C 1 -C 6 -alkoxycarbonyl-C 6 -C 6 alkyl for example methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, (1-methylethoxycarbonyl) methyl, n-butoxycarbonylmethyl, (1-methylpropoxycarbonyl) methyl, (2-methylpropoxycarbonyl) methyl, (1,1-dimethylethoxycarbonyl) methyl, n-pentoxycarbonylmethyl, (1-methylbutoxycarbonyl) methyl, (2-methylbutoxycarbonyl) methyl, (3-methylbutoxycarbonyl) methyl, (1,1-dimethylpropoxycarbonyl) methyl, ( 1,2-dimethylpropoxycarbonyl) methyl, (2,2-dimethylpropoxycarbonyl) methyl, (1-ethylpropoxycarbonyl) ethyl, n-hexoxycarbonylmethyl, (1-methylpentoxycarbonyl) methyl, (2-
  • Ci-Ce-alkyloximino-Ci-Ce-alkyl e.g. methoximino-methyl, ethoximino-methyl, n-propoximinomethyl, (1-methylethoximino) methyl, n-butoximino-methyl, (1-methylpropoximino) methyl, ( 2-methylpropoximino) methyl, (1,1-dimethylethoximino) methyl, n-pentoximino-methyl, (1-methylbutoximino) methyl, (2-methylbutoximino) methyl, (3-methylbutoximino) methyl, (2 , 2-dimethylpropoximino) methyl, (1-ethylpropoximino) methyl, n-hexoximino-methyl, (1, 1-dimethylpropoximino) methyl, (1,2-dimethylpropoximino) methyl, (1-methylpentoximino) methyl , (2-Methylpentoximino) methyl, (3-
  • Di- (-C 6 alkoxy) -C 2 -C 6 alkyl for example 2,2-dimethoxyethyl, 2,2-diethoxyethyl, 2,2-di- (n-propoxy) ethyl, 2,2-di - (1-methylethoxy) ethyl, 2,2-dibutoxyethyl, 2,2-di- (1-methylpropoxy) ethyl, 2,2-di- (2-methylpropoxy) ethyl, 2,2-di- (1, 1-dimethylethoxy) ethyl, 2- (ethoxy) -2- (methoxy) ethyl, 2- (methoxy) -2- (propoxy) ethyl, 2- (methoxy) -2- (1-methylethoxy) ethyl,
  • Di- (-C 6 alkylthio) -C 2 -C 6 alkyl for example 2,2- (dimethylthio) ethyl, 2,2- (diethylthio) ethyl, 2,2-di (n-propylt- hio) ethyl, 2,2-di- (1-methylethylthio) ethyl, 2,2- (dibutylthio) ethyl, 2,2-di- (1-methylpropylthio) ethyl, 2,2-di- (2- methylpropylthio) ethyl, 2,2-di (1, 1-dimethylethylthio) ethyl, 2- (ethylthio) -2- (methylthio) ethyl, 2- (methylthio) -2- (propylthio) ethyl, 2- (Methylthio) -2- (1-methylethylthio) ethyl, 2- (
  • C 3 -C 6 haloalkenyl for example 2-chloroprop-2-enyl, 3-chloroprop-2-enyl, 2,3-dichloroprop , -2-enyl, 3, 3-dichloroprop-2-enyl, 2, 3,3-trichloroprop-2-enyl, 2,3-dichlorobut-2-enyl, 2-bromoprop-2-enyl, 3-bromoprop-2enyl, 2,3-dibromoprop-2-enyl, 3, 3- Dibromoprop-2-enyl, 2,3,3-tribromoprop-2-enyl and 2,3-dibromobut-2-enyl;
  • Ci-C ß -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-tri- fluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl,
  • Ci-C ⁇ -alkoxy such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, 1, 1-dimethylethoxy, n-pentoxy, 1-methylbutoxy, 2-methyl butoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 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-l-methylpropoxy and l-ethyl-2-methylpropoxy,
  • Ci-Ce-alkylthio such as methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methyl-propylthio,
  • Ci-C ß -alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl,
  • -CC 4 alkyl for example methyl, ethyl, n-propyl, 1-methylethyl,
  • C 3 -C 4 alkenyl or alkynyl for example prop-2-en-2-yl, n-but-2-en-2-yl, 2-methyl-prop-2-en-l-yl, prop-2 -in-l-yl,
  • C 3 -C 6 ⁇ cycloalkyl for example cyclopropyl, cyclopentyl, cyclohexyl;
  • C ⁇ ⁇ C 4 haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloroethyl, 2,2,2-trichloroethyl;
  • C 1 -C 4 cyanoalkyl for example cyanomethyl
  • -C-C 3 -alkoxycarbonyl-C] -C 4 -alkyl for example methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-methylethoxycarbonylmethyl, 2-methyl-propoxycarbonylmethyl, 1- (methoxycarbonyl) -eth-l-yl, 1- (ethoxycarbonyl) -eth- l-yl, 1- (1-methylethoxycarbonyl) -eth-l-yl, 1- (methoxycarbonyl) prop-1-yl, 1- (ethoxycarbonyl) prop-1-yl, 1- (methoxycarbonyl ) but-l-yl or 1- (ethoxycarbonyl) but-l-yl;
  • Alkyloximinoalkyl with a total of 6 carbon atoms e.g. Methoximino-methyl or ethoxyiminomethyl
  • Dialkyloxy or dialkylthioalkyl with a total of 8 carbon atoms e.g. 2,2-dimethyloxyethyl, 2,2-diethoxyethyl, 2,2- (dimethylthio) ethyl or 2,2- (diethylthio) ethyl;
  • Chloroalkylenyl e.g. 2-chloroprop-2-enyl; substituted phenyl or benzyl, e.g. 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl,
  • the substituted 3, 4, 5, 6-tetrahydrophthalimides of the formula I can be in the form of their agriculturally useful salts, the salts of bases in general which do not impair the herbicidal action of I being suitable.
  • Particularly suitable basic salts are those of the alkali metals, preferably sodium and potassium salts, those of the alkaline earth metals, preferably calcium and magnesium salts and the transition metals, preferably zinc and iron salts, and the ammonium salts, the one to four C ⁇ C 4 alkyl, hydroxy-Ci-C ⁇ alkyl substituents and / or can carry a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl (2-hydroxyethyl) ammonium salts , the phosphonium, sulfonium and sulfoxonium salts.
  • the compounds of the formula I can contain one or more centers of chirality and are then present as enantiomer or diastereomer mixtures.
  • the invention encompasses both the pure enantiomers or diastereomers and their mixtures. If desired, the isomers can be separated by the methods customary for this, for example by means of crystallization or chromato- graph on an optically active adsorbate. Optically active compounds I can also be obtained from the corresponding optically active starting materials.
  • R 1 a radical from the group 1.01-1.09, namely H, CH 3 , C 2 H 5 , nC 3 H 7 , iC 3 H 7 , nC 4 H 9 , iC 4 H 9 , sC 4 H 9 , tC 4 H 9
  • R 2 a residue from the group 2.01 - 2.05, namely H, F, Cl, Br, J
  • R 3 a radical from the group 3.01-3.11, namely H, F, Cl, Br, J, N0 2 , CN, CH 3 , CF 3 , OCH 3 , OCF 3
  • R 5 a residue from group 4.01 - 4.04, namely F, Cl, Br, J
  • R 6 a radical from the group 5.01-5.11, namely H, CH 3 , C 2 H 5 , nC 3 H 7 , iC 3 H 7 , nC 4 H 9 , iC 4 H 9 , sC 4 H 9 , tC 4 H 9 , nC 5 H n , nC 6 H 13
  • R 7 a residue from group 6.01 - 6.69 (table 1)
  • herbicides particularly preferred compounds I are listed in Table 2 below.
  • the "amino compound” is converted into a diazonium salt. This reacts with an olefin in the presence of a copper salt.
  • the "phenyldiazonium salt” is expediently obtained in a manner known per se in aqueous acid solution (for example hydrochloric acid, hydrobromic acid, sulfuric acid) by reacting an amino compound of the formula II with a nitrite such as sodium nitrite, potassium nitrite etc.
  • the unsaturated component III is then added in a suitable solvent (for example H 2 O, acetone, diethyl ketone, methyl ethyl ketone, acetonitrile, dioxane, THF, methanol, ethanol etc.) in the presence of a copper halide such as CuCl, CuBr, CuCl2, CuBr2.
  • a suitable solvent for example H 2 O, acetone, diethyl ketone, methyl ethyl ketone, acetonitrile, dioxane, THF, methanol, ethanol etc.
  • the reactions can be carried out at temperatures from (-30) ° C to + 80 ° C.
  • the components of the diazotization reaction are usually used in a stoichiometric ratio, but an excess of one or the other component can be advantageous.
  • the copper halide is generally used in a stoichiometric ratio, but an excess or deficit can be advantageous.
  • the “phenyldiazonium salt” can be obtained in a manner known per se in anhydrous systems (for example glacial acetic acid, dioxane, absolute ethanol, THF, acetonitrile, acetone) with a nitrous acid ester such as tert-butyl nitrite, isopentyl nitrite etc. become.
  • the diazotization can take place in the presence of the olefin component III and the copper halide, or before the addition of the latter two components.
  • the compounds of the formula I can be obtained in a manner known per se by hydrogenation of compounds of the formula IV: Hydrogenation
  • reducing agents are elemental metals such as iron, tin, zinc etc., hydrogen in the presence of suitable catalysts (eg Pd / C, Pt / C, Raney-Ni etc.), complex hydrides such as LiAlH 4 , NaBH 4 , etc. - optionally in the presence of catalysts - in
  • the solvents used, in coordination with the reducing agent are usually acids such as acetic acid, propionic acid etc., alcohols such as methanol, ethanol etc., ethers such as diethyl ether, methyl tert-butyl ether, THF, dioxane etc., aromatics such as benzene, toluene etc. or corresponding mixtures.
  • acids such as acetic acid, propionic acid etc.
  • alcohols such as methanol, ethanol etc.
  • ethers such as diethyl ether, methyl tert-butyl ether, THF, dioxane etc.
  • aromatics such as benzene, toluene etc. or corresponding mixtures.
  • the reactions can be carried out at temperatures from (-100) ° C. to the reflux temperature of the particular solvent or solvent mixture.
  • the starting materials are usually used in a stoichiometric ratio, but an excess of one or the other component can be advantageous in individual cases.
  • Chlorine and bromine are suitable as R 5 * and fluorine and iodine as "R 5 ".
  • the reactions are usually carried out in a temperature range from (-30) ° C. to the reflux temperature of the particular solvent or mixture.
  • the starting materials are used in a stoichiometric ratio, but an excess or deficit of one or the other component, up to about 10 mol%, can be advantageous.
  • the compounds of the formula I can furthermore be obtained in a manner known per se by condensing an anhydride of the formula VI with an aniline of the formula V in an inert organic solvent or diluent.
  • Suitable solvents / diluents are alkane carboxylic acids such as acetic acid, propionic acid and isobutyric acid, alkane carboxylic acid esters such as ethyl acetate, aprotic solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone etc., aromatics such as toluene, xylene, etc. If an aprotic solvent is used, this is recommended continuous removal of the water of reaction formed or an acid catalysis (with, for example, p-toluenesulfonic acid, (trifluoro) methanesulfonic acid etc.).
  • the reactions are usually carried out in a temperature range from 0 ° C. to the reflux temperature of the solvent or mixture.
  • the starting materials are used in a stoichiometric ratio, but an excess or deficit of one or the other component, up to about 10 mol%, can be advantageous.
  • the compounds of the formula V can be obtained, for example, in a manner known per se (Houben-Weyl, vol. XI / 1, 4th edition 1957, p. 431ff) by reducing the corresponding nitro compounds VII:
  • a reducing agent such as B. elemental metals such as iron, tin, zinc etc., hydrogen in the presence of suitable catalysts (e.g. Pd / C, Pt / C, Raney-Ni etc.), complex hydrides such as LiAlH 4 , NaBH 4 , etc. - if necessary in the presence of catalysts - into consideration.
  • suitable catalysts e.g. Pd / C, Pt / C, Raney-Ni etc.
  • complex hydrides such as LiAlH 4 , NaBH 4 , etc. - if necessary in the presence of catalysts - into consideration.
  • the solvents used, in coordination with the reducing agent are usually acids, e.g. Acetic acid, propionic acid etc., alcohols such as methanol, ethanol etc., ethers such as diethyl ether, methyl tert-butyl ether, THF, dioxane etc., aromatics such as benzene, toluene etc., or corresponding mixtures.
  • acids e.g. Acetic acid, propionic acid etc.
  • alcohols such as methanol, ethanol etc.
  • ethers such as diethyl ether, methyl tert-butyl ether, THF, dioxane etc.
  • aromatics such as benzene, toluene etc., or corresponding mixtures.
  • the reactions can be carried out at temperatures from (-100) ° C. to the reflux temperature of the respective solvent or mixture.
  • the starting materials are usually used in a stoichiometric ratio, but in individual cases an excess of one or the other component, up to about 10 mol%, can be advantageous.
  • the compounds I or the herbicidal compositions comprising them and their environmentally compatible salts of alkali metals and alkaline earth metals can control weeds and grass weeds very well in crops such as wheat, rice, corn, soybeans and cotton without damaging the crop plants, an effect which occurs especially at low application rates.
  • the compounds I and their salts or the herbicidal compositions comprising them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, and also high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, Pastes, dusts, spreading agents or granules by spraying, atomizing, 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.
  • the compounds I are generally suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions.
  • Mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, as well as coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone or strongly polar solvents such as N-methylpyrrolidone or water.
  • 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, adhesive agent, dispersant or emulsifier and possibly solvent or oil can also be prepared 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 and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol, tributylphenyl polygly
  • 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 soils 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, A monium 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: I 20 parts by weight of compound no. 1.01 are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide , 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of ricinus 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.
  • V 20 parts by weight of active ingredient no. 1.05 are mixed with 2 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 .
  • Parts of a paraffinic mineral oil intimately mixed. A stable oily dispersion is obtained.
  • the herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active substances are less compatible with certain crop plants, application techniques can be used in which the herbicidal the means are sprayed with the help of sprayers so that the leaves of the sensitive crops are not hit as far as possible, while the active ingredients get onto the leaves of unwanted plants growing underneath or the uncovered floor area (post-directed, lay-by).
  • the application rates of active ingredient are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, the season, the target plants and the growth stage.
  • the substituted 3,4,5,6-tetrahydrophthalimides I or agents containing them can also be used in a further number of crop plants for eliminating unwanted plants.
  • crops botanical names
  • Trifolium pratense Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.
  • the tetrahydrophthalimides I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • diazines, 4H-3, 1-benzoxazine derivatives, benzothiadiazinones, 2, 6-dinitroanilines, N-phenylcarbamates, thiol carbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uraciles, benzofurander come as mixing partners vate, cyclohexane-l, 3-dione derivatives, which in the 2-position, for example Wear carboxy or carbimino group, quinoline carboxylic acid derivatives, imidazolinones, sulfonamides, sulfonylureas, aryloxy, heteroaryloxyphenoxypropionic acid and their salts, esters
  • Table 3 lists particularly preferred substituted 3,4,5,6-tetrahydrophthalimides of the formula I which were prepared in accordance with Example 1. Table 3:
  • 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.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the vessels were sprinkled lightly to promote germination and growth and then covered with transparent plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
  • test plants were treated with the active ingredients suspended or emulsified in water only at a height of 3 to 15 cm, depending on the growth habit.
  • the application rate for post-emergence treatment was 60, 31.3 or 15.6 g / ha of active substance.
  • the plants were kept at 10-25 ° C and 20-35 ° C depending on the species.
  • the trial period lasted 2 to 4 weeks.
  • the plants were cared for and their reaction to the individual treatments was evaluated. Evaluation was carried out 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 greenhouse experiments were carried out on Abutilon theophrasti, Amaranthus retroflexus, Chenopodium album, Euphorbia heterophylla, Galium aprina, Ipomoea spp., Solanum nigrum, Veronica subspecies and Zea mays.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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Abstract

3,4,5,6-tétrahydrophtalimides substitués (I) où R1 = H, alkyle en C¿1?-C6; R?2¿ = H, halogène; R3 = H, halogène, NO¿2?, CN, CH3, CH3 1 à 3 fois substitué par un halogène, OCH3, OCH3 1 à 3 fois substitué par un halogène; R?5¿ = halogène; R6 = H, alkyle en C¿1?-C6; R?7¿ = H, alkyle en C¿1?-C6 éventuellement substitué, alcényle en C3-C6, alcinyle en C3-C6, cycloalkyle en C3-C6, di-(C1-C6-alcoxy)-C2-C6-alkyle, di-(C1-C6-alkylthio)-C2-C6-alkyle, halogénoalcényle en C3-C6, phényle ou benzyle éventuellement substitué, ainsi que leurs sels, où R?7¿ n'est ni un CH¿3?, ni un C2H5, dans le cas où R?2¿ est un H ou un F et R3 est un Cl, et R5 est un Cl ou un Br et R6 est un H; procédé de fabrication des composés (I) et leur utilisation.
PCT/EP1993/003039 1992-11-11 1993-10-30 3,4,5,6-tetrahydrophtalimides substitues utilises comme herbicides et/ou comme defoliants ou comme siccatifs WO1994011344A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU54633/94A AU5463394A (en) 1992-11-11 1993-10-30 Substituted 3,4,5,6-tetrahydrophthalimides for use as herbicides and/or defoliants or desiccants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19924237984 DE4237984A1 (de) 1992-11-11 1992-11-11 Substituierte 3,4,5,6-Tetrahydrophthalimide, deren Herstellung und Verwendung
DEP4237984.9 1992-11-11

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WO1994011344A1 true WO1994011344A1 (fr) 1994-05-26

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Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0834503B1 (fr) * 1992-04-25 2001-06-27 Basf Aktiengesellschaft Tétrahydrophtalimides, leur préparation et utilisation
DE4438578A1 (de) * 1994-10-28 1996-05-02 Basf Ag Substituierte Phthalimido-Zimtsäurederivate und Zwischenprodukte zu ihrer Herstellung

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0240659A2 (fr) * 1986-02-07 1987-10-14 BASF Aktiengesellschaft 3,4,5,6-Tétrahydrophtalimide N-substituées et leurs précurseurs
EP0300398A2 (fr) * 1987-07-23 1989-01-25 BASF Aktiengesellschaft Dérivés d'acides 3-phénylpropioniques
EP0385231A1 (fr) * 1989-02-25 1990-09-05 BASF Aktiengesellschaft Utilisation de dérivés du N-phényl-3,4,5,6-tétrahydrophtalimide pour la dessication et l'excision d'organes de plantes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0240659A2 (fr) * 1986-02-07 1987-10-14 BASF Aktiengesellschaft 3,4,5,6-Tétrahydrophtalimide N-substituées et leurs précurseurs
EP0300398A2 (fr) * 1987-07-23 1989-01-25 BASF Aktiengesellschaft Dérivés d'acides 3-phénylpropioniques
EP0385231A1 (fr) * 1989-02-25 1990-09-05 BASF Aktiengesellschaft Utilisation de dérivés du N-phényl-3,4,5,6-tétrahydrophtalimide pour la dessication et l'excision d'organes de plantes

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DE4237984A1 (de) 1994-05-19

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