WO1994011344A1

WO1994011344A1 - Substituted 3,4,5,6-tetrahydrophthalimides for use as herbicides and/or defoliants or desiccants

Info

Publication number: WO1994011344A1
Application number: PCT/EP1993/003039
Authority: WO
Inventors: Elisabeth Heistracher; Gerhard Hamprecht; Ralf Klintz; Peter Schaefer; Uwe Kardorff; Karl-Otto Westphalen; Matthias Gerber; Helmut Walter
Original assignee: Basf Aktiengesellschaft
Priority date: 1992-11-11
Filing date: 1993-10-30
Publication date: 1994-05-26
Also published as: DE4237984A1; AU5463394A

Abstract

Described are substituted 3,4,5,6-tetrahydrophthalimides of formula (I) in which R1 = H or C¿1?-C6 alkyl; R?2¿ = H or halogen; R3 = H, halogen, NO¿2?, CN, CH3, CH3 substituted with 1 to 3 halogen atoms, OCH3 or OCH3 substituted with 1 to 3 halogen atoms; R?5¿ = halogen; R6 = H or C¿1?-C6 alkyl; R?7¿ = H, optionally substituted C¿1?-C6 alkyl, C3-C6 alkenyl, C3-C6 alkinyl, C3-C6 cycloalkyl, di-(C1-C6-alkoxy)-C2-C6-alkyl, di-(C1-C6-alkylthio)-C2-C6-alkyl, C3-C6 haloalkenyl or optionally substituted phenyl or benzyl, as well as their salts, wherein R?7¿ is not CH¿3? or C2-H5 when R?2¿ is H or F and R3 is Cl and R5 is Cl or Br and R6 is H. Also described are methods of preparing compounds of formula (I) and their use.

Description

SUBSTITUTED 3,4,5,6-TETRAHYDROPHTHALIMIDES AS HERBICIDES AND / OR DEFOLIANT OR DESSICANT

description

The present invention relates to new substituted 3, 4, 5, 6-tetrahydrophthaliird.de of the general formula I

in which the substituents have the following meaning:

R ^{1 is} hydrogen or a Ci-Cε-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 ⁵ halogen;

R ^{6 is} hydrogen or Ci-Cβ-alkyl;

R ^{7 is} hydrogen, Ci-Cε-alkyl, C ₃ -C ₆ ~ alkenyl, C ₃ -C ₆ ~ alkynyl, C ₃ -C _G -cycloalkyl, Ci-Cε-haloalkyl, Cι-C ₆ -cyanoalkyl, Cι-C ₆ -alkoxy-C ₆ -alkyl, -C-C ₆ -alkylthio-Cι-C ₆ -alkyl, Cι-C ₆ -alkoxycarbonyl-Ci-C _ß -alkyl, Cι-C ₆ -alkyloximino-Cι- 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,

Phenyl or benzyl, where the phenyl rings can each carry one to three residues, selected from the group consisting of halogen, cyano, nitro, Ci-Cg-alkyl, Cx-C _ß -haloalkyl, Ci-Cε-alkoxy, Ci-Cε- Haloalkoxy, Ci-Cε-alkylthio, Ci-Cε-haloalkylthio and Ci-Cε-alkoxycarbonyl,

as well as the agriculturally useful salts of I, where 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. It is known that 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.

Accordingly, the 3,4,5,6-tetra-hydrophthalimides of the formula I defined above were found. We have also found herbicidal compositions which contain these substances and have a good herbicidal action.

It has also been found that the compounds of the formula I are also suitable as defoliating and desiccating agents.

The meanings given above for the substituents R ¹ , R ² , R ³ , R ⁵ , R ⁶ , R ⁷ represent collective terms for individual lists of the individual group members. All alkyl, alkenyl, alkynyl, haloalkyl , Cyanoalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, haloalkenyl groups can be straight-chain or branched, unless stated otherwise. The haloalkyl, haloalkoxy, haloalkylthio and haloalkenyl radicals can carry the same or different halogen atoms.

Specifically, for example:

Halogen: fluorine, chlorine, bromine, and iodine;

Cι-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,

1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,

2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl- l-methylpropyl and l-ethyl-2-methylpropyl. With regard to the intended use, compounds of the formula I are preferred in which the substituents have the following meaning:

R ^{1 is} hydrogen or Ci-Cε-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,

Chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, difluorochloromethyl, fluorodichloromethyl;

Methoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy;

especially chlorine, 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-3-en-l-yl, 2-methyl-but-3-en- l-yl, 3-methylbut-3-en-l-yl, 1, 1-dimethylprop-2-en-l-yl, 1,2-dimethylprop-l-en-l-yl, 1,2- Dimethyl-prop-2-en-l-yl, l-ethyl-prop-l-en-2-yl, 1-ethyl-prop-2-en-l-yl, n-hex-1-en-l- yl, n-hex-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-l-yl, n-hex-5-en-l-yl, 1-methyl-pent-1-en-l-yl, 2-methyl-pent-l-en-l-yl, 3-methyl-pent-1-en-l-yl, 4-methyl-pent-l- en-l-yl, 1-methyl-pent-2-en-l-yl, 2-methyl-pent-2-en-l-yl, 3-methyl-pent-2-en-l-yl, 4- Methyl-pent-2-en-l-yl, 1-methyl-pent-3-en-l-yl, 2-methyl-pent-3-en-l-yl, 3-methyl-pent-3-en- l-yl, 4- Methyl-pent-3-en-l-yl, 1-methyl pent-4-en-l-yl, 2-methyl-pent-4-en-l-yl, 3-methyl-pent-4-en-l-yl, 4-methyl-pent-4-en-l- yl, 1, 1-dimethyl-but-2-en-l-yl, 1, l-dimethyl-but-3-en-l-yl, 1,2-dimethyl-but-1-en-l-yl, 1,2-dimethyl-but-2-en-l-yl, 1,2-dimethyl-but-3-en-l-yl, 1, 3-dimethyl-but-l-en-l-yl, 1, 3-dimethyl-but-2-en-l-yl, 1,3-dimethyl-but-3-en-l-yl, 2,2-dimethyl-but-3-en-l-yl, 2, 3- Dimethyl-but-l-en-l-yl, 2,3-dimethylbut-2-en-l-yl, 2,3-dimethyl-but-3-en-l-yl, 3,3-dimethyl but-1-en-l-yl, 3,3-dimethyl-but-2-en-l-yl, 1-ethyl-but-1-en-l-yl, l-ethyl-but-2-en- l-yl, l-ethyl-but-3-en-l-yl, 2-ethyl-but-l-en-l-yl, 2-ethyl-but-2-en-l-yl, 2-ethyl but-3-en-l-yl, 1, 1,2-trimethylprop-2-en-l-yl, l-ethyl-l-methyl-prop-2-en-l-yl, l-ethyl-2- methyl-prop-1-en-l-yl and l-ethyl-2-methyl-prop-2-en-l-yl;

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, n-hex-l-in-6-yl, n-hex-2-in -l-yl, n-hex-2-in-4-yl, n-hex-2-in-5-yl, n-hex-2-in-6-yl, n-hex-3-in-l -yl, n-Hex-3-in-2-yl, 3-methyl-pent-1-in-1-yl, 3-methyl-pent-1-in-3-yl, 3-methyl-pent-1 -in-4-yl, 3-methyl-pent-1-in-5-yl, 4-methyl-pent-1-in-1-yl, 4-methyl-pent-2-in-4-yl and 4 -Methyl-pent-2-in-5-yl;

C ₃ -C ₆ cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;

-C-C ₆ 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 _δ- 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 _δ- 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, (1,3-dimethylbutoxy) methyl, (2,2-dimethylbutoxy) methyl, (2nd , 3-dimethylbutoxy) methyl, (3,3-dimethylbutoxy) methyl, (1-ethylbutoxy) methyl, (2-ethylbutoxy) methyl, (1,1,2-trimethylpropoxy) methyl, (1,2,2- Trimethylpropoxy) methyl, (1-ethyl-l-methylpropoxy) methyl, (l-ethyl-2-methylpropoxy) methyl, methoxyethyl, ethoxyethyl, n-propoxyethyl, (1-methylethoxy) ethyl, n-butoxyethyl, (1- Methylpropoxy) ethyl, (2-methylpropoxy) et ethyl, (1,1-dimethylethoxy) ethyl, n-pentoxyethyl, (1-methylbutoxy) ethyl, (2-methylbutoxy) ethyl, (3-methylbutoxy) ethyl, (2,2-dimethylpropoxy) ethyl, (1- Ethylpropoxy) ethyl, (2,2-dimethylpropoxy) ethyl, (1-ethylpropoxy) ethyl, n-hexoxyethyl, (1,1-dimethylpropoxy) ethyl, (1,2-dimethylpropoxy) ethyl, (1-methylpentoxy) ethyl , (2-methylpentoxy) ethyl, (3-methylpentoxy) ethyl, (4-methylpentoxy) ethyl, (1,1-dimethylbutoxy) ethyl, (1,2-dimethylbutoxy) ethyl, (1,3-dimethylbu - toxy) ethyl, (2,2-dimethylbutoxy) ethyl, (2,3-dimethylbutoxy) ethyl, (3,3-dimethylbutoxy) ethyl, (1-ethylbutoxy) ethyl, (2-ethylbutoxy) ethyl, (1 , 1,2-trimethylpropoxy) ethyl, (1,2,2-trimethylpropoxy) ethyl, (1-ethyl-l-methylpropoxy) ethyl, (l-ethyl-2-methylpropoxy) ethyl, 2- (methoxy) propyl , 3- (methoxy) propyl, 2- (ethoxy) propyl;

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-methylpentylthio) methyl, (3-methyl - pentylthio) methyl, (4-methylpentylthio) methyl, (1,1-dimethylbutylthio) methyl, (1,2-dimethylbutylthio) methyl, (1,3-di- methylbutylthio) methyl, (2,2-dimethylbutylthio) methyl, (2,3-dimethylbutylthio) methyl, (3,3-dimethylbutylthio) methyl, (1-ethylbutylthio) methyl, (2-ethylbutylthio) methyl, (1,1, 2-trimethylpropylthio) methyl, (1,2,2-trimethylpropylthio) methyl, (l-ethyl-l-methylpropylthio) methyl,

(l-ethyl-2-methylpropylthio) methyl, methylthioethyl, ethylthioethyl, n-propylthioethyl, (1-methylethylthio) ethyl, n-butylthioethyl, (1-methylpropylthio) ethyl, (2-methylpropylthio) ethyl, (1 , 1-dimethylethylthio) ethyl, n-pentylthioethyl, (1-methylbutylthio) ethyl, (2-methylbutylthio) ethyl, (3-methylbutylthio) ethyl, (2,2-dimethylpropylthio) ethyl, (1-ethylpropylthio) ethyl, n-hexylthioethyl, (1,1-dimethylpropylthio) ethyl, (1,2-dimethylpropylthio) ethyl, (1-methylpentylthio) ethyl, (2-methylpentylthio) ethyl, (3-methylpentylthio) ethyl , (4-methylpentylthio) ethyl, (1,1-dimethylbutylthio) ethyl, (1,2-dimethylbutylthio) ethyl, (1,3-dimethylbutylthio) ethyl, (2,2-dimethylbutylthio) ethyl, (2nd , 3-dimethylbutylthio) ethyl, (3,3-dimethylbutylthio) ethyl, (1-ethylbutylthio) ethyl, (2-ethylbutylthio) ethyl, (1, 1, 2-trimethylpropylthio) ethyl, (1, 2,2-trimethylpropylthio) ethyl,

(1-ethyl-l-methylpropylthio) ethyl, (l-ethyl-2-methylpropylthio) ethyl, 2- (methylthio) propyl, 3- (methylthio) propyl and 2- (ethylthio) propyl;

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-methylpentoxycarbonyl) methyl, (3- Methylpentoxycarbonyl) methyl, (4-methylpentoxycarbonyl) methyl, (1,1-dimethylbutoxycarbonyl) methyl, (1,2-dimethylbutoxycarbonyl) methyl, (1,3-dimethylbutoxycarbonyl) methyl, (2,2-dimethylbutoxycarbonyl ) methyl, (2,3-dimethylbutoxycarbonyl) methyl, (3,3-dimethylbutoxycarbonyl) methyl, (1-ethylbutoxycarbonyl) methyl, (2-ethylbutoxycarbonyl) methyl, (1, 1, 2-trimethylpropoxycarbonyl) methyl, (1,2,2-trimethylpropoxy-carbony1) met yl, (1-ethyl-met ylpropxycarbony1) methyl, (l-ethyl-2-methylpropylcarbonyl) methyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propoxycarbonylethyl , (1-Methylethoxycarbonyl) ethyl, n-butoxycarbonylethyl, (1-Methylpropoxycarbonyl) ethyl, (2-Methylpropoxycarbonyl) ethyl, (1,1-Dimethyl- ethoxycarbonyl) ethyl, n-pentoxycarbonylethyl, (1-methylbutoxycarbonyl) ethyl, (2-methylbutoxycarbonyl) ethyl, (3-methylbutoxycarbonyl) ethyl, (1, 1-dimethylpropoxycarbonyl) ethyl, (1,2-dimethylpropoxycarbonyl) ethyl , (2,2-Dimethylpropoxycarbonyl) ethyl, (1-ethylpropoxycarbonyl) ethyl, n-hexoxycarbonylethyl, (1-methylpentoxycarbonyl) ethyl, (2-methylpentoxycarbonyl) ethyl, (3-methylpentoxycarbonyl) ethyl, (4th -Methylpentoxycarbonyl) ethyl, (1, 1-dimethylbutoxycarbonyl) ethyl, (1,2-dimethylbutoxycarbonyl) ethyl, (1,3-dimethylbutoxycarbonyl) ethyl, (2,2-dimethylbutoxycarbonyl) ethyl, (2,3- Dimethylbutoxycarbonyl) ethyl, (3,3-dimethylbutoxycarbonyl) ethyl, (1-ethylbutoxycarbonyl) ethyl, (2-ethylbutoxycarbonyl) ethyl, (1,1,2-trimethylpropoxycarbonyl) ethyl, (1,2,2 Trimethylpropoxycarbonyl) ethyl, (1-ethyl-l-methyl-propoxycarbonyl) ethyl, (l-ethyl-2-methylpropylcarbonyl) ethyl, 3- (methoxycarbonyl) propyl, 2- (methoxycarbonyl) propyl and 2- (ethoxycarbonyl) propyl;

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-Methylpentoximino) methyl, (4-Methylpentoximino) methyl, (1,1-Dimethylbutoxi ino) methyl, (1,2-Dimethylbutoximino) methyl, (1,3- Dimethylbutoximino) methyl, (2,2-dimethylbutoximino) methyl, (2,3-dimethylbutoximino) methyl, (3,3-dimethylbutoximino) methyl, (1-ethylbutoximino) methyl, (2-ethylbutoximino) methyl , (1,1,2-Trimethylpropoximino) methyl, (1,2,2-trimethylpropoximino) methyl, (1-ethyl-l-methylpropoximino) methyl, (l-ethyl-2 -methylpropoximino) methyl, methoximino-ethyl, ethoximino-ethyl, n-propoximino-ethyl, (1-methylethoximino) ethyl, n-butoximino-ethyl, (1-methyl-propoximino) ethyl, (2-methylpropoximino) ethyl, (1,1-dimethylethoximino) ethyl, n-pentoximinoethyl, (1-methylbutoximino) ethyl, (2-methylbutoximino) ethyl, (3-methylbutoximino) ethyl, (2,2-dimethylpropoximino) ethyl, ( 1-ethylpropoximino) ethyl, n-hexoximino-ethyl, (1, 1-dimethylpropoximino) ethyl, (1,2-dimethylpropoximino) ethyl, (1-methylpentoximino) ethyl, (2-methylpentoximino) ethyl, (3-methylpentoximino) ethyl, (4-methylpentoximino) ethyl, (1,1-dimethylbutoximino) ethyl, (1,2-dimethylbutoximino) ethyl, (1,3-dimethylbut- oximino) ethyl, (2,2-dimethylbutoximino) ethyl, (2, 3-dimethylbutoximino) ethyl, (3, 3-dimethylbutoximino) ethyl, (1-ethylbutoximino) ethyl, (2-ethylbutoximino) ethyl, ( 1, 1, 2-trimethylpropoximino) ethyl, (1,2,2-trimethylpropoximino) ethyl, (1-ethyl-l-methylpropoximino) ethyl, (l-ethyl-2-methylpropoximino) ethyl, 2- ( Methoximino) propyl, 3- (methoximino) propyl and 2- (ethoximino) propyl;

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,

2- (butoxy) -2 (methoxy) ethyl, 2- (methoxy) -2- (1-methylpropoxy) ethyl, 2- (methoxy) -2- (2-methylpropoxy) ethyl, 2- (1.1 -Dimethylethoxy) -2- (methoxy) ethyl, 2- (ethoxy) -2- (propoxy) ethyl, .2- (ethoxy) -2- (1-methylethoxy) ethyl, 2- (butoxy) -2 ( ethoxy) ethyl, 2- (ethoxy) -2- (1-methylpropoxy) ethyl, 2- (ethoxy) -2- (2-methylpropoxy) ethyl, 2- (ethoxy) -2- (1.1 -dimethylethoxy) ethyl, 2- (1-methylethoxy) -2- (propoxy) ethyl, 2- (butoxy) -2- (propoxy) ethyl, 2- (1-methylpropoxy) -2 (propoxy) ethyl, 2 - (2-Methylpropoxy) -2- (propoxy) ethyl, 2- (1,1-dimethylethoxy) -2- (propoxy) ethyl, 2- (butoxy) -2- (1-methylethoxy) ethyl , 2- (1-methylethoxy) -2- (1-methylpropoxy) ethyl, 2- (1-methylethoxy) -2- (2-methylpropoxy) ethyl, 2- (1, 1-dimethylethoxy) -2 - (1-methylethoxy) ethyl, 2- (butoxy) -2- (1-methylpropoxy) ethyl, 2- (butoxy) -2- (2-methylpropoxy) ethyl, 2- (butoxy) -2- (1st , 1-dimethylethoxy) ethyl, 2- (1-methyl-propoxy) -2- (2-methyl-propoxy) ethyl, 2- (1,1-dimethyl-ethoxy) -2- (1-methylpropoxy) ethyl and 2 - (1, 1-dimethylethoxy) -2- (2- methylpropoxy) 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- (butylthio) -2- (methylthio) ethyl, 2- (methylthio) -2- (1-methylpropylthio) ethyl, 2- (methyl- thio) -2- (2-methylpropylthio) ethyl, 2- (1,1-dimethylethylthio) -2- (methylthio) ethyl, 2- (ethylthio) -2- (propylthio) ethyl, 2- ( Ethylthio) -2- (1-methyl-ethylthio) ethyl, 2- (butylthio) -2- (ethylthio) ethyl, 2- (ethylthio) -2- (1-methylpropylthio) ethyl, 2- (ethylthio) -2- (2-methylpropylthio) ethyl, 2- (ethylthio) -2- (1,1-dimethylethylthio) ethyl, 2- (l-methylethylthio) -2- (propylthio) ethyl, 2- (butylthio) -2- (propylthio) ethyl, 2- (1- Methylpropylthio) -2- (propylthio) ethyl,

2- (2-methylpropylthio) -2 (propylthioethyl), 2- (1,1-dimethylethylthio) -2- (propylthio) ethyl, 2- (butylthio) -2- (1-methylethylthio) ethyl, 2 - (l-methylethylthio) -2- (1-methylpropylthio) ethyl, 2- (1-methylethylthio) -2- (2-methylpropylthio) ethyl, 2- (1, 1-dimethylethylthio) -2- ( 1-methylethylthioethyl, 2- (butylthio) -2- (1-methylpropylthio) ethyl, 2- (butylthio) -2- (2-methylpropylthio) ethyl, 2- (butylthio) -2- (1 , 1-dimethylethylthio) ethyl, 2- (1-methylpropylthio) -2- (2-methylpropylthio) ethyl, 2- (l, 1-dimethylethylthio) -2- (1-methylpropylthio) ethyl and 2- ( 1, 1-dimethylethylthio) -2- (2-methylpropylthio) ethyl;

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;

Phenyl or benzyl, where the phenyl radicals can carry up to 3 of the following substituents:

- halogen, cyano, nitro, Ci-Cβ-alkyl,

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,

Pentafluoroethyl and 3-chloropropyl,

Ci-Cε-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,

2-methylpropylthio, 1, 1-dimethylethylthio, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-l-methylpropylthio and l-ethyl- 2-methylpropylthio,

Ci-C _ß -alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl,

1, 1-dimethylethoxycarbonyl, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxy- carbonyl, hexoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-Dime¬ thylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-l- methylpropoxycarbonyl and l-ethyl-2-methylpropylcarbonyl;

in particular R ⁷

-CC ₄ alkyl, for example methyl, ethyl, n-propyl, 1-methylethyl,

1-methylpropyl, 2-methylpropyl;

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,

2-methyl-prop-2-yn-l-yl;

C ₃ -C ₆ ~ cycloalkyl, for example cyclopropyl, cyclopentyl, cyclohexyl;

Cι ~ 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 1 -C ₄ -alkoxy-C $ -alkyl or C 1 -C ₄ -alkylthio -CC-C -alkyl, for example methoxymethyl, methoxyethyl, methylthiomethyl or methylthioethyl;

-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,

4-trifluoromethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 1-methoxycarbonylphenyl, 2-methoxycarbonylphenyl, 3-methoxycarbonylphenyl, 4-methoxycarbonylphenyl, phenyl, benzyl.

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.

With regard to the use of the substituents 3, 4, 5, 6-tetrahydrophthalimides of the formula I as herbicidal and / or defoliant / desiccant compounds, the variables preferably have the following meanings:

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)

the radicals R ¹ , R ² , R ³ , R ⁵ , R ⁶ and R ⁷ can be combined with one another as desired, with the proviso that R ^{7 may} only be 6.01, 6.04 - 6.69 if R ² = hydrogen or fluorine and R ³ = chlorine and R ⁵ = chlorine or bromine and R ⁶ = hydrogen.

Table 1

With regard to the use as herbicides, particularly preferred compounds I are listed in Table 2 below.

Table 2

0

5

_Q The compounds of the formula I can be obtained in a variety of ways analogously to known reaction methods. Some procedures are explained below as examples:

Method A 5

Compounds of the formula I with R ⁵ = Cl, Br are obtained in a manner known per se {cf. MP Doyle, B. Siegfried, RC Elliot JF Dellaria, J. Org. Chem. 42, 2431 (1977)}, by reacting a compound of formula II and a compound of research _Q mel III arylation reaction in a Meerwein or a modification of it:

0

II III

In this type of reaction, 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.

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.

Compounds of the formula III are normally used in a large excess, but it can also be advantageous to use them in a small excess, stoichiometrically or in a deficit.

The copper halide is generally used in a stoichiometric ratio, but an excess or deficit can be advantageous.

Alternatively, 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.

It is advantageous to work at normal pressure or under the autogenous pressure of the particular solvent.

Procedure B

The compounds of the formula I can be obtained in a manner known per se by hydrogenation of compounds of the formula IV: Hydrogenation

Examples of 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

Consideration.

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.

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.

With regard to pressure, the information applies to method A.

Procedure C

Compounds of the formula I are also obtained from compounds of the formula I * by processes known from the literature or analogously to processes known from the literature (for example Houben-Weyl Vol. 5/3, pp. 145 ff, Vol. 5/4, p. 595ff) by exchanging R ^{5 *} for another halide. The starting materials can be obtained by processes A, B and D.

Chlorine and bromine are suitable as R ^{5 *} and fluorine and iodine as "R ⁵ ". As reagents z. B. metal fluorides and iodides, especially alkali fluorides and iodides, as well as organic fluorinating agents such as DAST (= diethylamino sulfur trifluoride) etc., in appropriately matched aprotic solvents or mixtures such as acetone, diethyl ketone, methyl ethyl ketone, dimethylformamide, diethylformamide, N-methylpyrrolidone, dimethyl - sulfoxide, sulfolane, chlorinated. Hydrocarbons such as methylene chloride, chloroform etc. can be used.

The reactions are usually carried out in a temperature range from (-30) ° C. to the reflux temperature of the particular solvent or mixture.

As a rule, 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.

Regarding the pressure, information applies to method A. Procedure D

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.

VI V

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.

With regard to pressure, the information applies to method A.

Procedure E

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:

As a reducing agent such. 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.

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.

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.

It is expedient to work at normal pressure or under the autogenous pressure of the particular solvent.

Procedure F

The compounds of formula VII with R ⁵ = chlorine, bromine are themselves in a manner known per se {cf. eg MP Doyle, B. Siegfried, RC Elliot, JF Dellaria, J. Org. Chem. 4.2, 2431 (1977)} by reacting an aniline of the formula VIII and a compound of the formula III in an arylation reaction according to Meerwein or a modification thereof available:

VIII III For this implementation, the information for method A applies.

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. For the production of emulsions, pastes or oil dispersions, the substrates as such or dissolved in an oil or solvent, by means of wetting agents, adhesives, dispersants or emulsifiers in water be homogenized. However, 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.

The alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols 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 polyglycol ether, alkyl aryl polyether alcohol alcohol, iso alcohol alcohol alcohol, iso Condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulfite waste liquors or methyl cellulose into consideration.

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.

II 20 parts by weight of compound no. 1.02 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenyl and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

III 20 parts by weight of the active ingredient. 1.03 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil consists. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.

IV 20 parts by weight of active ingredient no. 1.04 are mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight in powder form Silica gel mixed well and ground in a hammer mill. A fine spray mixture containing 0.1% by weight of the active ingredient is obtained by finely distributing the mixture in 20,000 parts by weight of water.

V 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.

In view of the versatility of the application methods, 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. For example, the following crops (botanical names) come into consideration:

Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spp. altissima, Beta vulgaris spp. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica) t, Cucusisasa- Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humomo lupansisump usita-tissimum, Lycopersicon lycopersicum, Malus spp., Manihot esculenta, Medicago sativa, Musa spp., Nicotiana tabacu

(N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spp., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, sorghum bicolor (see vulgar), Theobroma cacao,

Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

In order to broaden the spectrum of action and to achieve synergistic effects, the tetrahydrophthalimides I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. For example, 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 and amides and others into consideration.

It may also be useful to apply the compounds I alone or in combination with other herbicides, mixed with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.

example 1

N- {4-chloro-5- [2-chloro-2- (2,2,2-trifluoroethoxycarbonyl) ethyl-1] -2-fluorophenyl} -3,4,5,6-tetrahydrophthalimide (1.01)

To a suspension of 2.8 g of tert-butyl nitrite, 60 g of acrylic acid (2,2,2-trifluoroethyl) ester, 2.8 g of anhydrous copper (II) chloride in 200 ml abs. Acetonitrile was added dropwise 5.3 g of N- (5-amino-4-chloro-2-fluorophenyl) -3,, 5, 6-tetrahydrophthalimide in 20 ml abs. Acetonitrile. After stirring for 12 hours, dilute hydrochloric acid was added and the mixture was extracted with methyl tert-butyl ether. The combined organic phases were dried over sodium sulfate and then concentrated. The residue was purified by chromatography on silica gel (eluent: petroleum ether / ether = 2: 1). Yield: 1.6 g (19% of theory);

! H-NMR (in d ⁶ -DMSO / TMS as internal standard): δ [ppm] = 1.75 (brs; 4H); 2.37 (brs; 4H); 3.32 (m; 1H); 3.52 (dd; 1H); 4.77 - 5.05 (m; 3H); 7.55 (d; 1H); 7.75 (d; 1H)).

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:

Substituted 3,4,5,6-tetrahydrophthalimide I (R ¹ = H)

Examples of use

The herbicidal activity of the tetrahydrophthalimides of the formula I was demonstrated by greenhouse tests:

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.

In pre-emergence treatment, 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.

For the purpose of post-emergence treatment, the 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. During this time, 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.

The result showed that weeds can be combated very well with compounds Nos. 1.01 and 1.02.

Claims

1. Substituted 3, 4, 5, 6-tetrahydrophthalimides of the general formula I

in which the substituents have the following meaning:

R ^{1 is} hydrogen or a Ci-Cε-alkyl group;

R ^{2 is} hydrogen or halogen;

R ⁵ halogen;

R ^{6 is} hydrogen or -CC ₆ alkyl;

R ^{7 is} hydrogen, Ci-Cε-alkyl, C ₃ -C ₆ alkenyl, C ₃ -Cg alkynyl, C ₃ -C ₆ cycloalkyl, Cι-C ₆ haloalkyl, Ci-Cε-cyanoalkyl,

C ₁ -C ₆ -alkoxy-C ₆ -alkyl, C ₁ -C ₆ -alkylthio-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxycarbonyl-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkyloximino-C _6th -alkyl, di- (-C-C ₆ -alkoxy) -C ₂ -C ₆ -alkyl, di- (-C-C ₆ -alkylthio) -C ₂ -C6-alkyl, C ₃ -C ₆ ~ haloalkenyl,

Phenyl or benzyl, where the phenyl rings can each carry one to three radicals selected from the group consisting of halogen, cyano, nitro, Cχ-Cg-alkyl, Cx-Cε-haloalkyl, Cι-C ₆ alkoxy, Cι-C ₆ Haloalkoxy, Ci-Cε-alkylthio, Cι-C6-haloalkylthio and Ci-Cε-alkoxycarbonyl,

and the agriculturally useful salts of I, where R ^{7 is} not methyl or ethyl when 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 of the formula I according to claim 1, in which R ^{1 is} hydrogen, R ^{2 is} hydrogen or halogen, R ^{3 is} hydrogen, halogen, nitro, cyano, methyl, methoxy, trifluoromethyl or trifluoromethoxy, R ^{5 is} halogen , R ⁶ are hydrogen, C ~ alkyl, and R ⁷ are hydrogen, C alkyl, C ₃ -C alkenyl, C ₃ -C alkynyl, cyclopropyl, cyclopentyl, cyclohexyl, Cι-C ₂ -fluoro- or chloroalkyl , -C-C ₂ -Cyanoalkyl, Cι-C ₄ -alkoxy-Cχ-C ₄ -alkyl, Cι-C ₄ -alkylthio-Cι-C ₄ -alkyl, Cι-C -alkoxycarbonyl-Cι-C -alkyl, Cι- C -Alkyloximino- Cι-C alkyl, di (Cι-C ₄ alkoxy) -C ₂ -C ₄ -alkyl, di- (Cι-C ₄ -alkylthio) -C ₂ -C ₄ alkyl, C ₃ ~ C ₄ -fluoro- or chloroalkenyl, phenyl or benzyl, where the phenyl rings can each be substituted by one to three radicals selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl, methoxy and methoxycarbonyl.

Process for the preparation of substituted 3, 4, 5, 6-tetra-hydrophthalimides of the formula I according to claim 1, characterized in that a _' compound of the formula II

and a compound of formula III

subject to a Meerwein's arylation reaction.

4. A process for the preparation of substituted 3, 5, 6-tetra-hydrophthalimides of the formula I with R ⁶ = H, according to claim 1, characterized in that a compound of formula IV

hydrated

A process for the preparation of substituted 3, 4,5, 6-tetra-hydrophthalimides of the formula I, according to claim I, characterized in that R ⁵ = chlorine or bromine is replaced by fluorine or iodine.

A process for the preparation of substituted 3,4,5, 6-tetra-hydrophthalimides of the formula I according to claim 1, characterized in that an aniline of the formula V

with a tetrahydrophthalic anhydride of the formula VI

implements

7. A process for the preparation of substituted anilines of the formula V according to claim 6, characterized in that a nitro compound of the formula VII

10 reduced to aniline derivative V in the usual way,

8. A process for the preparation of substituted nitro compounds of the formula VII according to claim 7, characterized in that a compound of the formula VIII

subject to a Meerwein's arylation reaction.

9. Herbicidal composition containing a herbicidally effective amount

35 at least one substituted 3,4,5, 6-tetrahydrophthalimide of the formula I or its agriculturally useful salt, as claimed in claim 1, and customary inert additives.

10. agents for the desiccation and / or defoliation of plants,

40 containing a desiccant / defoliantly effective amount of at least one substituted 3, 4,5, 6-tetrahydrophthalimide of the formula I or its agriculturally useful salt, according to claim 1, and customary inert additives.

45 11. A method for controlling unwanted vegetation, characterized in that a herbicidally effective amount of at least one 3,4,5,6-tetrahydrophthalimide of the formula I or its agriculturally useful salt, according to claim 1, and customary inert additives on the plants, their seeds and / or their habitat.

12. A process for the desiccation and / or defoliation of plants, characterized in that a desiccant and / or defoliantly effective amount of at least one 3, 5, 6-tetra-hydrophthalimide of the formula I or its agriculturally useful salt, according to claim 1, and the usual inert additives can act on the plants.