DE4020072A1 - New oxazole di:carboximide derivs. - useful as herbicides and plant growth regulators - Google Patents

Abstract

Dicarboximides of formulae (Ia) and (Ib) and their salts are new. In the formulae, X = O or S; R1 = H; halo; 1-6C alkyl opt. mono- to penta-substd. by halogen and/or mono- or disubstd. by cyclopropyl, 1-4C alkoxy, etc or cyano; phenyl or phenyl-1-4C alkyl opt. mono-, di- or trisubstd. in the ring by 1-6C alkyl, 1-6C haloalkyl, etc 3-8C cycloalkyl opt. mono-, di- or trisubstd. by 1-4C alkyl or halogen; 2-6C alkenyl or 2-6C alkynyl opt. mono-, di- or trisubstd. by halogen or 1-3C alkoxy and/or monosubstd. by A; opt. halo-substd. 1-4C alkoxy or 1-4C alkylthio; OA; SA; or a 5-or 6- membered satd. or aromatic heterocyclic gp. contg. 1 or 2 N, S and/or O atoms and opt. mono- or disubstd. by 1-3C alkyl, halogen 1-3C alkoxy or 1-3C alkoxycarbonyl; R2 = H; OH; 1-4C alkoxy; 1-6C alkyl opt. mono-, di- or trisubstd. by cyano, 1-4C alkoxy-1-4C alkoxy, 1-4C alkoxy, 3-8C or A; 3-8C cycloalkyl opt. mono- di- or trisubstd. by 1-6C alkyl, 1-6C haloalkyl, 1-4C alkoxy etc; 3-6C alkenyl or 3-6C alkynyl opt. mono-, di- or trisubstd. by halogen and/or monosubstd. by A; di(1-4C alkyl)amino; or a 5- or 6-membered satd. or aromatic heterocyclic gp. contg. 1 or 2 N, S and/or O atoms and opt. mono-, di- or trisubstd. by 1-4C alkyl or halogen; or 1-4C alkoxycarbonyl; or naphthyl opt. mono-, di- or trisubstd. by 1-4C alkyl or halogen; A = phenyl opt. mono-, di- or trisubstd. by 1-4C alkyl, 1-4C haloalkyl, 1-4C alkoxy, 1-4C haloalkoxy, 1-4C alkylthio, 1-4C haloalkylthio, halogen, cyano or nitor; except 3-methylisoxazole-4,5-dicarboximide (Ic). USE - Cpds (Ia) and (Ib) are pre- and post-emergence herbicides and plant growth regulators. (Ia) and (Ib) are applied e.g. at a rate of 0.01-3 kg/ha.

Description

The present invention relates to dicarboximides of the formulas Ia and ib

in which the substituents have the following meaning:

X oxygen or sulfur;
R¹ is hydrogen; Halogen; C₁-C₆-alkyl which may carry one to five halogen atoms and / or one or two of the following radicals: cyclopropyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio or cyano ;
Phenyl or phenyl-C₁-C₄-alkyl, wherein the phenyl radical in each case unsubstituted or one to three times by C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio , C₁-C₆ haloalkylthio, halogen, cyano or nitro;
C₃-C₈cycloalkyl which is unsubstituted or substituted one to three times by C₁-C₄alkyl or halogen;
C₂-C₆-alkenyl, which may be substituted one to three times by halogen or C₁-C₃-alkoxy and / or once by phenyl, wherein the phenyl radical in turn may carry one to three of the following groups: C₁-C₄-alkyl, C₁- C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, cyano or nitro;
C₂-C₆-alkynyl, which may be substituted one to three times by halogen or C₁-C₃-alkoxy and / or once by phenyl, where the phenyl radical in turn may carry one to three of the following groups: C₁-C₄-alkyl, C₁- C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, cyano or nitro;
C₁-C₄ alkoxy; C₁-C₄-alkylthio; C₁-C₄-haloalkoxy; C₁-C₄-haloalkylthio;
Phenoxy or phenylthio which is unsubstituted or one to three times by C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, Cyano or nitro is substituted;
a 5- to 6-membered saturated or aromatic heterocyclic radical containing one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen which may carry one or two of the following substituents: C₁-C₃alkyl, halogen, C₁-C₃alkoxy and C₁-C₃ alkoxycarbonyl;
R² is hydrogen; hydroxyl; C₁-C₄ alkoxy;
C₁-C₆-alkyl which may carry one to three of the following groups: cyano, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁- C₄-haloalkylthio, di-C₁-C₄-alkylamino, halogen, C₃-C₈-cycloalkyl or phenyl, wherein the phenyl ring in turn can carry one to three of the following radicals: halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄ -Haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio or C₁-C₄-haloalkylthio;
C₃-C₈-cycloalkyl which may carry one to three of the following groups: C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, halogen, nitro or cyano;
C₃-C₆-alkenyl, which may be substituted one to three times by halogen and / or once by phenyl, wherein the phenyl radical in turn may carry one to three of the following groups: C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁- C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, cyano or nitro;
C₃-C₆-alkynyl which may be substituted one to three times by halogen and / or once by phenyl, wherein the phenyl radical in turn may carry one to three of the following groups: C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁- C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, cyano or nitro;
Di-C₁-C₄-alkylamino;
a 5- to 6-membered heterocyclic saturated or aromatic radical having one or two heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen, which may be substituted one to three times by C₁-C₄-alkyl or halogen;
Phenyl which may carry one to four of the following groups: C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, Nitro, cyano, formyl, C₁-C₄-alkanoyl, C₁-C₄-haloalkanoyl or C₁-C₄-alkoxycarbonyl;
Naphthyl, which may be substituted one to three times by C₁-C₄-alkyl or halogen,
and plant-tolerated salts of the dicarboxylic acid imides Ia and Ib, with the exception of 3-methylisoxylene-4,5-dicarboximide.

Moreover, the invention relates to processes for the preparation of the compounds Ia and Ib and herbicidal agents containing at least one compound Ia or Ib or 3-methylisoxazole-4,5-dicarboximide.

From Arch. Pharm. 320, 1281-83 (1987) Isoxazoldicarbonsäureimide with a Ethoxycarbonylmethylsubstitution in the 3-position known. Further is in J. Chem. Soc. Perkin Trans 1, 2391-4 (1982), the 3-methylisoxazole 4,5-dicarboximide described. Synthesis 1988, 449-52 teaches 5-amino Substituted Isothiazoldicarbonsäureimide as intermediates for Production of dyes. The cited prior art discloses no herbicidal properties of the compounds mentioned.

The object of the present invention was to provide novel herbicidally active compounds to find and synthesize.  

Accordingly, the above-defined dicarboxylic imides Ia and Ib found.

The dicarboxylic acid imides Ia and Ib according to the invention are available on various Because of production:

Way A

A process for the preparation of the compounds Ia and Ib consists in Reaction of dicarboxylic monoamides IIa-d with dehydrating Agents such as acetic anhydride, inorganic acid halides such as thionyl chloride, phosphorus (III) or phosphorus (V) halides such as Phosphorus trichloride or phosphorus pentachloride, phosgene or propanephosphonic anhydride (PPA).

The reaction is conveniently carried out by reacting the dicarboxylic acid monoamides IIa-d in an inert organic solvent and about molar amounts of the dehydrating agent, optionally also dissolved in an inert solvent, added dropwise. The dicarboxylic acid imides Ia and Ib can in the usual way z. B. by suction or extraction with an organic solvent from the crude Be isolated reaction mixture.

It is expedient to use as solvent for the reactions Halogenated hydrocarbons such as tetrachloroethane, dichloromethane, dichloroethane, Chlorobenzene, 1,2-dichlorobenzene and chloroform; Ethers, such as diethyl ether, Methyl tert-butyl ether, dimethoxyethane, diethylene glycol dimethyl ether, Tetrahydrofuran and dioxane, aromatics such as benzene, toluene and xylene or dimethylformamide and mixtures of these solvents.

The reactions can at temperatures from -20 ° C to the reflux temperature the particular solvent, preferably at -10 to 60 ° C, be performed.  

The molar ratios in which the required starting compounds are reacted together, are generally 0.9: 1 to 5: 1 (dehydrating agent: dicarboxylic acid amonoamide).

The concentration of the educts in the solvent mixture is in general 0.1 to 5 mol / l, preferably 0.2 to 2 mol / l.

The preparation of the dicarboxylic acid monoamides IIa used for this process are required as starting materials, is described in DE-A-38 12 225.

The dicarboxylic acid monoamides IIc can be used as in the older German Application P 39 31 627.0 described. Starting materials are Isoxazole and isothiazole-3-carboxylic acid halides VII, which with a Amine VIII to be implemented. As Carbonsäurehalogenide VII are the Chlorides are preferred. It is expediently done so that you can Carboxylic acid halide in an inert organic solvent such as Dichloromethane, or an ether such as diethyl ether or methyl tert-butyl ether with an amine VIII, also dissolved in an organic Solvent, brings to reaction. This is the amine VIII expediently in 2 to 5 times the molar amount, preferably 2 to 3 times the molar amount, one to the resulting hydrogen halide to tie. You can also in the presence of an auxiliary base such. B. one tertiary amine (triethylamine) work. In this case, 1 to 1.5 will suffice Molar equivalents of amine VIII. The reaction temperature can be between 0 and 50 ° C, preferably between 0 and 20 ° C. The reaction is in the general after 1 to 12 hours ended. The mixture can be as usual be worked up, for example by hydrolysis with water and Extraction of the product IX with an organic solvent and Concentration of the organic solvent.

From the isoxazole or isothiazolamides IX, the 3-aminocarbonylisoxazole 4-carboxylic acids or 3-aminocarbonyl-isothiazole-4-carboxylic acids of Formula IIc, by reaction with alkyllithium such as n-butyllithium, sec-butyllithium and methyllithium, preferably with the addition of an under the reaction conditions of inert solvent such as diethyl ether or Tetrahydrofuran. In general, this reaction is under an inert gas atmosphere, z. As nitrogen atmosphere, at temperatures between -70 and -80 ° C made. The alkyllithium compound is used in this Method generally in 2-3 times molar amount based on used amide of the formula IX used. After complete implementation the mixture is treated with carbon dioxide, preferably in one  inert solvents such as diethyl ether or z. B. tetrahydrofuran, where to obtain the desired products of formula IIc.

The required for this process as starting material isoxazole and Isothiazole-3-carboxylic acid halides VII are known from the literature or can from the corresponding carboxylic acids X in the usual manner getting produced.

The carboxylic acids X required for this process are known from the literature (Beilstein, Hauptwerk and 1-5 Supplementary Works, Volume 27, R.W. Wiley, The Chemistry of Heterocyclic Compounds, Five- and Six-Membered Compounds with Nitrogen and Oxygen, Interscience Publishers, New York, London (1962)) or can by generally literature methods, eg. B. by Oxidation from the corresponding alcohols or aldehydes or by Hydrolysis be prepared from the corresponding nitriles.

Way B

Another method for the synthesis of compounds of formula Ia is in the reaction of hydroxamic acid chlorides III with halomaleimides IV. This is conveniently done so that the haloimide IV in an inert organic solvent, about molar amounts of the hydroxamic acid chloride III is added and then an approximately double molar amount of a base is added dropwise. The mixture can be like  be worked up usual, z. B. by hydrolysis with water and suction or extraction of the product with an organic solvent and Concentration of the organic solvent.

It is expedient to use as solvent for these reactions Halogenated hydrocarbons such as dichloroethane, chlorobenzene, 1,2-dichlorobenzene, Tetrachloroethane, dichloromethane and chloroform; Ethers, such as diethyl ether; Methyl tert-butyl ether, dimethoxyethane, diethylene glycol dimethyl ether, Tetrahydrofuran and dioxane or aromatics such as benzene, toluene and Xylene or mixtures of these solvents.

The reactions can at temperatures from -10 ° C to 50 ° C, preferably at 0 to 30 ° C, are performed.

As bases preferably nitrogen bases such as 2-, 3-, 4-picoline, N, N-dimethylaniline, N, N-dimethylcyclohexylamine, triethylamine (TEA), Pyridine and 1,8-diazabicyclo (5.4.0) undec-7-ene (DBU).

The reactants are used in particular in a molar ratio of 1: 1, the nitrogen base is added in a doubled to threefold molar amount.

The concentration of the starting materials in the solvent mixture is generally 0.1 to 5 mol / l, preferably 0.2 to 2 mol / l.  

Way C

Another method for the synthesis of the compounds Ia consists in Oxidation of Isoxazolindicarbonsäureimiden VI, the z. B. produced are prepared by reacting hydroxamic acid chlorides III with maleimides V. It is expedient to proceed so that the maleimide V in a submitted linerten organic solvent, such as molar amounts of Hydroxamic acid chloride III is added and then an approximately molar amount a base dripped. The mixture can be worked up as usual, z. B. by hydrolysis with water and suction or extraction of the product with an organic solvent.

It is expedient to use as solvent for these reactions Halogenated hydrocarbons such as tetrachloroethane, dichloromethane, dichloroethane, Chlorobenzene, 1,2-dichlorobenzene and chloroform or aromatics such as Benzene, toluene and xylene or mixtures of these solvents.

The reactions can at temperatures from -10 to 50 ° C, preferably at 0 ° C to 30 ° C, are performed.

Bases are nitrogen bases such as 2-, 3-, 4-picoline, N, N, -dimethylaniline, N, N-dimethylcyclohexylamine, triethylamine (TEA), pyridine or 1,8-diazabicyclo (5.4.0) undec-7-ene (DBU).

The reactants are especially in molar ratios of 1 to 1,1: 1 (maleimide: hydroxamic acid chloride) used, the nitrogen base is added in the simple to double molar amount.

The concentration of the starting materials in the solvent mixture is generally 0.1 to 5 mol / l, preferably 0.2 to 2 mol / l.

The isoxazole dicarboximides Ia are obtained by dehydrogenation of the isoxazoline imides VI accessible. It is expediently done so that you can Isoxazolinimid VI is presented in an inert organic solvent and mixed with about molar amounts of oxidizing agent.  

The solvents used for the dehydrogenation are in particular aromatic Hydrocarbons such as benzene, toluene or xylene into consideration.

The oxidizing agent used is preferably sodium hypochlorite, nitrobenzene or quinones such as 2,3,5,6-tetrachloro-p-benzoquinone or 5,6-dichloro 2,3-dicyano-p-benzoquinone (DDQ).

The reactions can at temperatures of 50 ° C to the boiling point the solvent used are carried out.

The reactants can be used in a molar ratio of 1: 1 to 1:10 (isoxazolineimide: oxidizing agent) be used.

With regard to the intended use of the compounds Ia and Ib come as substituents preferably the following radicals into consideration:

X oxygen or sulfur,
R¹ is hydrogen,
Halogen, such as fluorine, chlorine, bromine, iodine, especially fluorine and chlorine;
C₁-C₆-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1- Dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 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 1-methylpropyl and 1-ethyl-2-methylpropyl, in particular methyl, ethyl, propyl, 1-methylethyl and 1,1-dimethylethyl, which contains one to five halogen atoms such as fluorine, chlorine, bromine, iodine, in particular fluorine and chlorine, and / or one or two of the following radicals; cyano; cyclopropyl; Alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy, especially methoxy, ethoxy, 1-methylethoxy and 1,1-dimethylethoxy; Haloalkoxy such as difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-1,1, 2-trifluoroethoxy and pentafluoroethoxy, especially trifluoromethoxy and pentafluoroethoxy; Alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio, especially methylthio and ethylthio; Halogenoalkylthio, such as difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio and pentadluoroethylthio, especially trifluoromethylthio and pentafluoroethylthio;
Phenyl or phenyl-C₁-C₄-alkyl, e.g. B. benzyl or phenylethyl, wherein the phenyl each unsubstituted or one to three times by alkyl having 1 to 6, in particular 1 to 4 carbon atoms as mentioned above, in particular methyl, ethyl and 1-methylethyl; Haloalkyl as mentioned above, in particular trifluoromethyl and chlorodifluoromethyl; Alkoxy as mentioned above, in particular methoxy and ethoxy; Haloalkoxy as mentioned above, in particular trifluoromethoxy, trichloromethoxy and pentafluoroethoxy; Alkylthio as mentioned above, in particular methylthio and ethylthio; Haloalkylthio as mentioned above, in particular difluoromethylthio, trifluoromethylthio and pentafluoromethylthio; Halogen as mentioned above, in particular fluorine and chlorine; Cyano or nitro is substituted;
C₃-C₈cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, in particular cyclopropyl, cyclopentyl and cyclohexyl; the one to three times by alkyl as mentioned above, in particular methyl and ethyl; or halogen as mentioned above, in particular fluorine and chlorine, may be substituted;
C₂-C₆ alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2- Methyl 1-propenyl, 2-methyl-2-propenyl, 1-ethylethyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-2-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2- pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3 butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-D imethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3- Dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2- butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl 1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, especially ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl , 2-butenyl, 3-butenyl, 1-methylpropenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, which is one to three times by halogen as mentioned above, in particular fluorine and chlorine; or alkoxy as mentioned above, in particular methoxy and ethoxy; and / or may be substituted once by phenyl, wherein the phenyl radical in turn may carry one to three of the following groups: alkyl as mentioned above, in particular methyl, ethyl and 1-methylethyl; Haloalkyl as mentioned above, in particular trifluoromethyl and chlorofluoromethyl; Alkoxy as mentioned above, in particular methoxy and ethoxy; Haloalkoxy as mentioned above, in particular trifluoromethoxy, trichloromethoxy and pentafluoroethoxy; Alkylthio as mentioned above, in particular methylthio and ethylthio; Haloalkylthio as mentioned above, in particular difluoromethylthio, trifluoromethylthio and pentafluoromethylthio; Halogen as mentioned above, in particular fluorine and chlorine; Cyano or nitro;
C₂-C₆ alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4- Pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 3-methyl 1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3 butinyl and 1-ethyl-1-methyl-2-propynyl, in particular ethynyl, 1-propynyl and 2-propynyl, which is one to three times by halogen as mentioned above, in particular iodine; or alkoxy as mentioned above, in particular methoxy and ethoxy; and / or may be substituted once by phenyl, wherein the phenyl radical in turn may carry one to three of the following groups: alkyl as mentioned above, in particular methyl, ethyl and 1-methylethyl; Haloalkyl as mentioned above, in particular trifluoromethyl and chlorodifluoromethyl; Alkoxy as mentioned above, in particular methoxy and ethoxy; Haloalkoxy as mentioned above, in particular trifluoromethoxy, trichloromethoxy and pentafluoroethoxy; Alkylthio as mentioned above, in particular methylthio and ethylthio;
Haloalkylthio as mentioned above, in particular difluoromethylthio, trifluoromethylthio and pentafluoromethylthio; Halogen as mentioned above, in particular fluorine and chlorine; Cyano or nitro;
C₁-C₄-alkoxy as mentioned above, in particular methoxy and ethoxy;
C₁-C₄-haloalkoxy as mentioned above, in particular trifluoromethoxy, trichloromethoxy and pentafluoroethoxy;
C₁-C₄-alkylthio as mentioned above, in particular methylthio and ethylthio;
C₁-C₄-haloalkylthio as mentioned above, in particular difluoromethylthio, trifluoromethylthio and pentafluoroethylthio;
Phenoxy or phenylthio which is substituted one to three times by alkyl as mentioned above, especially methyl, ethyl and 1-methylethyl; Haloalkyl as mentioned above, in particular trifluoromethyl and chlorofluoromethyl; Alkoxy as mentioned above, in particular methoxy and ethoxy; Haloalkoxy as mentioned above, in particular trifluoromethoxy, trichloromethoxy and pentafluoroethoxy; Alkylthio as mentioned above, in particular methylthio and ethylthio; Haloalkylthio as mentioned above, in particular difluoromethylthio, trifluoromethylthio and pentafluoromethylthio; Halogen as mentioned above, in particular fluorine and chlorine or nitro; may be substituted;
a 5- to 6-membered saturated or aromatic heterocyclic radical containing one or two heteroatoms selected from the group oxygen, sulfur, nitrogen such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl , 4-tetrahydropyranyl, 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4 -Oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl , 2-pyridyl, 3-pyridyl and 4-pyridyl, which may carry one or two of the following substituents: alkyl as mentioned above, in particular methyl; Halogen as mentioned above, in particular fluorine and chlorine; Alkoxy as mentioned above, in particular methoxy and ethoxy; or alkoxycarbonyl, such as methoxycarbonyl and ethoxycarbonyl, in particular methoxycarbonyl;
R² is hydrogen; hydroxyl; C₁-C₄-alkoxy as mentioned under R¹, in particular methoxy and ethoxy;
C₁-C₆-alkyl as mentioned under R¹, in particular methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, 1,1-dimethylpropyl, 1,1-dimethylbutyl, 1 , 2-dimethylpropyl, which may carry one to three of the following groups: alkoxy-alkoxy such as methoxy-methoxy, ethoxy-ethoxy in particular methoxy-methoxy, alkoxy as mentioned under R¹, in particular methoxy and ethoxy; Haloalkoxy as mentioned under R¹, in particular trifluoromethoxy; Alkylthio as mentioned under R¹, in particular methylthio and ethylthio; Halogenalkylthio as mentioned under R¹, in particular trifluoromethylthio; Dialkylamino, especially dimethylamino and diethylamino; Halogen as mentioned under R¹, in particular fluorine and chlorine; Cycloalkyl as mentioned for R¹, in particular cyclopropyl, cyclopentyl and cyclohexyl, or phenyl may be substituted, wherein the phenyl radical in turn may carry one to three of the following groups: halogen; cyano; nitro; Alkyl as mentioned under R¹, in particular methyl and ethyl; Haloalkyl as mentioned under R¹, in particular trifluoromethyl; Alkoxy as mentioned under R¹, in particular methoxy and ethoxy; Haloalkoxy as mentioned under R¹, in particular trifluoromethoxy; Alkylthio as mentioned under R¹, in particular methylthio and ethylthio; or haloalkylthio as mentioned under R¹, in particular trifluoromethylthio;
C₃-C₈-cycloalkyl as mentioned under R¹, in particular cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; which may carry one to three of the following groups: alkyl as mentioned under R¹, in particular methyl, ethyl and 1-methylethyl; Haloalkyl as mentioned under R¹, in particular trifluoromethyl; Alkoxy as mentioned under R¹, in particular methoxy and ethoxy; Haloalkoxy as mentioned under R¹, in particular trifluoromethoxy; Halogen as mentioned under R¹, in particular fluorine and chlorine; Nitro or cyano;
C₃-C₆-alkenyl as mentioned under R¹, in particular 2-propenyl, 1-methyl-2-propenyl, 1,1-dimethyl-2-propenyl and 2-butenyl, which is one to three times by halogen as mentioned under R¹, in particular Fluorine and chlorine, and / or may be substituted once by phenyl, wherein the phenyl radical in turn may carry one to three of the following groups: alkyl as mentioned under R¹, in particular methyl and ethyl; Haloalkyl as mentioned under R¹, in particular trifluoromethyl; Alkoxy as mentioned under R¹, in particular methoxy and ethoxy; Haloalkoxy as mentioned under R¹, in particular trifluoromethoxy; Alkylthio as mentioned under R¹, in particular methylthio and ethylthio; Halogenalkylthio as mentioned under R¹, in particular trifluoromethylthio; Halogen as mentioned under R¹, in particular fluorine and chlorine; Cyano or nitro;
C₃-C₆-alkynyl as mentioned under R¹, in particular 2-propynyl, 1-methyl-2-propynyl and 1,1-dimethyl-2-propynyl; which is one to three times by halogen as mentioned under R¹, in particular fluorine and chlorine; and / or may be substituted once by phenyl, wherein the phenyl radical in turn may carry one to three of the following groups: alkyl as mentioned under R¹, in particular methyl and ethyl; Haloalkyl as mentioned under R¹, in particular trifluoromethyl; Alkoxy as mentioned under R¹, in particular methoxy and ethoxy; Haloalkoxy as mentioned under R¹, in particular methylthio and ethylthio; Halogenalkylthio as mentioned under R¹, in particular trifluoromethylthio; Halogen as mentioned under R¹, in particular fluorine and chlorine; Cyano or nitro;
C₁-C₄ dialkylamino, especially dimethylamino and diethylamino;
a 5- to 6-membered heterocyclic radical having one or two heteroatoms selected from the group oxygen, sulfur or nitrogen as mentioned under R¹, which is one to three times by alkyl as mentioned under R¹, in particular methyl, ethyl and 1-methylethyl; or halogen as mentioned under R¹. in particular fluorine and chlorine may be substituted;
Phenyl which may carry one to four of the following groups: alkyl as mentioned under R¹, in particular methyl, ethyl and 1-methylethyl; Haloalkyl as mentioned under R¹, in particular trifluoromethyl; Alkoxy as mentioned under R¹, in particular methoxy and ethoxy; Haloalkoxy as mentioned under R¹, in particular trifluoromethoxy; Alkylthio as mentioned under R¹, in particular methylthio and ethylthio; Halogenalkylthio as mentioned under R¹, in particular trifluoromethylthio; Halogen as mentioned under R¹, in particular fluorine and chlorine; Nitro, cyano, formyl; C₁-C₄ alkanoyl such as acetyl, propionyl, butyryl, in particular acetyl; Haloalkanoyl such as trifluoroacetyl, trichloroacetyl, pentafuoropropionyl, especially trifluoroacetyl; or alkoxycarbonyl as mentioned under R¹, in particular methoxycarbonyl;
Naphthyl which may be substituted one to three times by alkyl as mentioned under R¹, in particular methyl and ethyl, or halogen as mentioned under R¹, in particular fluorine and chlorine.

Examples of herbicidally active compounds of the formula Ia and Ib are detailed below:

wherein each R¹ has the following meaning:

Hydrogen, fluorine, chlorine, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopropyl, cyclo-butyl, cyclo-pentyl, cyclohexyl, cycloheptyl, cyclo-octyl, 1-methylcyclopropyl, cyclopropylmethyl, 1- (cyclopropyl) ethyl, chloromethyl, dichloromethyl, trichloromethyl, Chlorodifluoromethyl, trifluoromethyl, pentafluoroethyl, difluoromethyl, 1-chloroethyl, 2-chloroethyl, 1-methyl-1-chloroethyl, 1-methyl-2-chloroethyl, Methoxymethyl, 1-methylmethoxymethyl, 1-methyl-2-methoxyethyl, 1-methylethoxymethyl, Ethoxymethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-ethylethenyl, 2-phenylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-propynyl, Methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 1,1-dimethylethoxy, methylthio, ethylthio, chlorodifluoromethoxy, trifluoromethoxy, Trichloromethylthio, phenyl, 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, 2,4-dichlorophenyl, 2,4,6-trimethylphenyl, Phenoxy, phenylthio, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 2,4-dichlorophenoxy, benzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl.

wherein each R¹ has the following meaning:

Hydrogen, fluorine, chlorine, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopropyl, cyclo-butyl, cyclo-pentyl, cyclohexyl, cycloheptyl, cyclo-octyl, 1-methylcyclopropyl, cyclopropylmethyl, 1- (cyclopropyl) ethyl, chloromethyl, dichloromethyl, trichloromethyl, Chlorodifluoromethyl, trifluoromethyl, pentafluoroethyl, difluoromethyl, 1-chloroethyl, 2-chloroethyl, 1-methyl-1-chloroethyl, 1-methyl-2-chloroethyl, Methoxymethyl, 1-methylmethoxymethyl, 1-methyl-2-methoxyethyl, 1-methylethoxymethyl, Ethoxymethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-ethylethenyl, 2-phenylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-propynyl, Methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 1,1-dimethylethoxy, methylthio, ethylthio, chlorodifluoromethoxy, trifluoromethoxy, Trichloromethylthio, phenyl, 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, 2,4-dichlorophenyl, 2,4,6-trimethylphenyl, Phenoxy, phenylthio, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 2,4-dichlorophenoxy, benzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl.

wherein each R¹ has the following meaning:

Hydrogen, fluorine, chlorine, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopropyl, cyclo-butyl, cyclo-pentyl, cyclohexyl, cycloheptyl, cyclo-octyl, 1-methylcyclopropyl, cyclopropylmethyl, 1- (cyclopropyl) ethyl, chloromethyl, dichloromethyl, trichloromethyl, Chlorodifluoromethyl, trifluoromethyl, pentafluoroethyl, difluoromethyl, 1-chloroethyl, 2-chloroethyl, 1-methyl-1-chloroethyl, 1-methyl-2-chloroethyl,  Methoxymethyl, 1-methylmethoxymethyl, 1-methyl-2-methoxyethyl, 1-methylethoxymethyl, Ethoxymethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-ethylethenyl, 2-phenylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-propynyl, Methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 1,1-dimethylethoxy, methylthio, ethylthio, chlorodifluoromethoxy, trifluoromethoxy, Trichloromethylthio, phenyl, 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, 2,4-dichlorophenyl, 2,4,6-trimethylphenyl, Phenoxy, phenylthio, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 2,4-dichlorophenoxy, benzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl.

wherein each R¹ has the following meaning:

Hydrogen, fluorine, chlorine, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopropyl, cyclo-butyl, cyclo-pentyl, cyclohexyl, cycloheptyl, cyclo-octyl, 1-methylcyclopropyl, cyclopropylmethyl, 1- (cyclopropyl) ethyl, chloromethyl, dichloromethyl, trichloromethyl, Chlorodifluoromethyl, trifluoromethyl, pentafluoroethyl, difluoromethyl, 1-chloroethyl, 2-chloroethyl, 1-methyl-1-chloroethyl, 1-methyl-2-chloroethyl, Methoxymethyl, 1-methylmethoxymethyl, 1-methyl-2-methoxyethyl, 1-methylethoxymethyl, Ethoxymethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-ethylethenyl, 2-phenylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-propynyl, Methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 1,1-dimethylethoxy, methylthio, ethylthio, chlorodifluoromethoxy, trifluoromethoxy, Trichloromethylthio, phenyl, 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, 2,4-dichlorophenyl, 2,4,6-trimethylphenyl, Phenoxy, phenylthio, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy,  2,4-dichlorophenoxy, benzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl.

wherein each R¹ has the following meaning:

Hydrogen, fluorine, chlorine, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopropyl, cyclo-butyl, cyclo-pentyl, cyclohexyl, cycloheptyl, cyclo-octyl, 1-methylcyclopropyl, cyclopropylmethyl, 1- (cyclopropyl) ethyl, chloromethyl, dichloromethyl, trichloromethyl, Chlorodifluoromethyl, trifluoromethyl, pentafluoroethyl, difluoromethyl, 1-chloroethyl, 2-chloroethyl, 1-methyl-1-chloroethyl, 1-methyl-2-chloroethyl, Methoxymethyl, 1-methylmethoxymethyl, 1-methyl-2-methoxyethyl, 1-methylethoxymethyl, Ethoxymethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-ethylethenyl, 2-phenylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-propynyl, Methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 1,1-dimethylethoxy, methylthio, ethylthio, chlorodifluoromethoxy, trifluoromethoxy, Trichloromethylthio, phenyl, 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, 2,4-dichlorophenyl, 2,4,6-trimethylphenyl, Phenoxy, phenylthio, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 2,4-dichlorophenoxy, benzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl.

wherein each R¹ has the following meaning:

Hydrogen, fluorine, chlorine, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopropyl, cyclo-butyl, cyclo-pentyl, cyclohexyl, cycloheptyl, cyclo-octyl, 1-methylcyclopropyl, cyclopropylmethyl, 1- (cyclopropyl) ethyl, chloromethyl, dichloromethyl, trichloromethyl, Chlorodifluoromethyl, trifluoromethyl, pentafluoroethyl, difluoromethyl, 1-chloroethyl, 2-chloroethyl, 1-methyl-1-chloroethyl, 1-methyl-2-chloroethyl, Methoxymethyl, 1-methylmethoxymethyl, 1-methyl-2-methoxyethyl, 1-methylethoxymethyl, Ethoxymethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-ethylethenyl, 2-phenylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-propynyl, Methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 1,1-dimethylethoxy, methylthio, ethylthio, chlorodifluoromethoxy, trifluoromethoxy, Trichloromethylthio, phenyl, 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, 2,4-dichlorophenyl, 2,4,6-trimethylphenyl, Phenoxy, phenylthio, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 2,4-dichlorophenoxy, benzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl.

Salts of the compounds of the formulas Ia and Ib are agricultural usable salts, for example alkali metal salts, such as the potassium or Sodium salt, alkaline earth metal salts, such as the calcium, magnesium or Barium salt, manganese, copper, zinc or iron salts and ammonium, Phosphonium, sulfonium or sulfoxonium salts, for example ammonium salts, Tetraalkylammonium salts, benzyltrialkylammonium salts, trialkylsulfonium salts or Trialkylsulfoxoniumsalze into consideration.

The herbicidal and growth-regulating compounds according to the invention Ia and Ib or the agents containing them can be used, for example, in Form of directly sprayable solutions, powders, suspensions, also high percentage  aqueous, oily or other suspensions or dispersions, Emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, misting, dusting, scattering or Pouring be applied. The forms of use depend on the intended use; In any case they should be as fine as possible to ensure the active compounds of the invention.

The compounds Ia and Ib are generally suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions. When inert additives come from mineral oil fractions from medium to high Boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic Hydrocarbons, eg. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, Propanol, butanol, cyclohexanol, cyclohexanone, chlorobenzene, isophorone or strongly polar solvents such as N, N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.

Aqueous application forms can be prepared from emulsion concentrates, dispersions, Pastes, wettable powders or water-dispersible granules by addition to be prepared from water. For the preparation of emulsions, pastes or oil dispersions may be the substrates as such or in an oil or Solvent dissolved by means of wetting, adhesion, dispersing or emulsifying agent be homogenized in water. It can also be more effective Substance, wetting, adhesion, dispersing or emulsifying agent and possibly Solvent or oil existing concentrates are produced, the Dilution with water are suitable.

As surface-active substances are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. As lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as fatty acids, alkyl and alkylarylsulfonates, Alkyl, lauryl ether and fatty alcohol sulfates, as well as salts sulfated hexa-, hapta- and octadecanols, as well as 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 ethers, alkylaryl polyether alcohols, isotridecyl alcohol, Fatty alcohol ethylene oxide condensates, ethoxylated castor oil, Polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, Sorbitol esters, lignin-sulphite liquors or methylcellulose in Consideration.  

Powders, litter and dusts can be mixed or mixed Grinding the active substances with a solid carrier become.

Granules, for. B. coated, impregnated and homogeneous granules be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths such as silica gel, silicas, silica gels, Silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, Dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground Plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products, such as cereal flour, Bark, wood and nutshell flour, cellulose powder or other solid Carriers.

The formulations contain between 0.1 and 95% by weight, preferably between 0.5 and 90 wt .-%, active ingredient. The active ingredients are in one Purity from 90% to 100%, preferably 95% to 100% (according to NMR spectrum) used.

The compounds I according to the invention can be, for example, as follows be formulated:

• I. Mix 90 parts by weight of compound No. 1,001 10 parts by weight of N-methyl-α-pyrrolidone and receives a solution, which is suitable for use in the form of very small drops.
• II. 20 parts by weight of compound no. 1.001 are in one Mixture dissolved, consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of Dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100 000 parts by weight Water gives an aqueous dispersion, the 0.02 wt .-% of the active ingredient.
• III. 20 parts by weight of compound no. 1.001 are in one Mixture dissolved, consisting of 40 parts by weight of cyclohexanone, 30 parts by weight Isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide 1 mole of castor oil exists. By pouring and finely distributing the  Solution in 100 000 parts by weight of water gives an aqueous Dispersion containing 0.02 wt .-% of the active ingredient.
• IV. 20 parts by weight of the active ingredient No. 1.001 are in one Mixture dissolved, consisting of 25 parts by weight of cyclohexanone, 65 parts by weight a mineral oil fraction of boiling point 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and fine Distributing the solution in 100 000 parts by weight of water is obtained an aqueous dispersion containing 0.02% by weight of the active ingredient.
• V. 20 parts by weight of the active ingredient No. 1.001 are with 3 parts by weight the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid a sulphite waste liquor and 60 parts by weight of powdered Silica gel well mixed and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight Water gives a spray mixture containing 0.1 wt .-% of the active ingredient contains.
• VI. 3 parts by weight of the active ingredient No. 1,001 are used with 97 parts by weight finely divided kaolin mixed. You get that way a dust containing 3% by weight of the active ingredient.
• VII. 30 parts by weight of the active substance No. 1.001 are with a Mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil, which is on the surface of this Silica gel was sprayed, intimately mixed. You get up this way, a preparation of the active substance with good adhesion.
• VIII. 20 parts by weight of the active ingredient No. 1,001 are used with 2 parts by weight Calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight Fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a Phenol-urea-formaldehyde condensates and 68 parts by weight a paraffinic mineral oil intimately mixed. You get one stable oily dispersion.

The application of the herbicidal and growth-regulating agents or the Active ingredients can be pre-emergence or postemergence. are the active ingredients for certain crops less compatible, so can Application techniques are applied, in which the herbicidal agents  be sprayed with the help of sprayers so that the leaves of sensitive crops are not taken if possible while the active ingredients on the leaves underneath are growing more unwanted Plants or the uncovered ground surface arrive (post-directed, lay-by).

The application rates of active ingredient when used as herbicides are ever by target, season, ornamentals and growth stage 0,001 to 3, preferably 0.1 to 2 kg / ha of active substance (a.

In view of the detectable activity spectrum for weed control, the Compatibility with crops or the desired influence of crops Growth of the same and in view of the variety of application methods can the compounds of the invention in a large number of Crop plants are used. Consider, for example following cultures:

Botanical name German name Allium cepa onion Pineapple comosus pineapple Arachis hypogaea Peanut Asparagus officinalis asparagus Beta vulgaris spp. altissima sugar beet Beta vulgaris spp. rapa mangel Brassica napus var. Napus rape Brassica napus var. Napobrassica Turnip Brassica rapa var. Silvestris rape Camellia sinensis Teestrauch Carthamus tinctorius Safflower Färbedistel Carya illinoinensis Pecan Citrus limon lemon Citrus sinensis Orange, orange Coffea arabica (Coffea canephora, Coffea liberica) coffee Cucumis sativus cucumber Cynodon dactylon Bermuda grass Daucus carota carrot Elaeis guineensis oil palm Fragaria vesca strawberry Glycine max Soybean Gossypium hersutum (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) cotton Helianthus annuus sunflower Hevea brasiliensis Para rubber tree Hordeum vulgare barley Humulus lupulus hop Ipomoea batatas sweet potatoes Juglans regia walnut tree Lens culinaris lens Linum usitatissimum flax Lycopersicon lycopersicum tomato Malus spp. Apple Manihot esculenta manioc Medicago sativa alfalfa Musa spp. Fruit and flour banana Nicotiana tabacum (N. rustica) tobacco Olea europaea olive tree Oryza sativa rice Phaserolus lunatus butterbean Phaseolus vulgaris bush bean Picea abies Rotfichte Pinus spp. pine Pisum sativum garden pea Prunus avium sweet cherry Prunus dulcis almond Prunus persica peach Pyrus communis pear Ribes sylvestre Red currant Ricinus communis castor-oil plant Saccharum officinarum sugarcane Secale cereal rye Solanum tuberosum potato Sorghum bicolor (see vulgare) sorghum Theobroma cacao cacao Trifolium pratense Red clover Triticum aestivum wheat Triticum durum durum wheat Vicia faba horse beans Vitis vinifera grapevine Zea mays Corn

To broaden the spectrum of action and to achieve synergistic Effects can be the compounds of formula I both with each other and also with representatives of other herbicidal or growth-regulating active ingredient groups  mixed and applied together. For example, come as mixing partner diazine, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiolcarbamates, halocarboxylic acids, Triazines, amides, ureas, diphenyl ethers, triazinones, Uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives, quinolinecarboxylic acid derivatives, Sulfonylurea derivatives, (hetero) -aryloxy-phenoxypropionic acids, their salts, esters and amides and others.

In addition, it may be useful to use the compounds Ia or Ib alone or in combination with other herbicides also with other pesticides mixed together, for example, with funds for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which be used to address nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

The following examples illustrate the preparation of the compounds Ia and Ib.

N-tert-Butyl-3-isopropyl-isoxazol-4,5-dicarboximide

To 5.1 g (20.0 mmol) of 5-tert-butylaminocarbonyl-3-isopropylisoxazole 4-carboxylic acid in 200 ml of dichloromethane was added dropwise at -5 ° C in succession 7.5 g (74.1 mmol) of methylmorpholine, 2.4 g (20 mmol) of dimethylaminopyridine and 17.4 g of a 50% solution of propanephosphonic anhydride (27.3 mmol) in dichloromethane and then heated under reflux for 6 h. you The solvent was removed in vacuo and the residue was taken up in 300 ml of ethyl acetate and extracted twice with saturated sodium bicarbonate solution and once each with 5% citric acid solution, saturated Sodium carbonate solution and saturated sodium chloride solution. The organic Phase was dried over magnesium sulfate and the solvent in vacuo deducted. 4.1 g (87%) of N-tert-butyl-3-isopropyl-isoxazole were obtained. 4,5-dicarboximide as a solid, mp. 60-62 ° C (Example No. 1.003).

8.5 g (45.3 mmol) of chloromaleic acid tert-butylimide in 100 ml of dry Toluene was added at 0 ° C with 5.5 g (45.3 mmol) of 2-methyl-propylhydroxamylchlorid in 100 ml of toluene. Then added dropwise at 0 ° C 9.6 g (94.9 mmol) of triethylamine and stirred for 12 h at room temperature. you filtered, extracted the filtrate with 10% HCl, dried the organic phase over magnesium sulfate and stripped off the solvent in vacuo. 7.9 g (74%) of N-tert-butyl-3-isopropyl-isoxazole-4,5- dicarboximide (physical data see above).  

N-tert-Butyl-3-isopropyl-isothiazol-4,5-dicarboximide

To 5.4 g (20 mmol) of 5-tert-butylaminocarbonyl-3-isopropylisothiazole 4-carboxylic acid in 200 ml of dichloromethane was added dropwise at -5 ° C in succession 7.5 g (74.1 mmol) methylmorpholine, 2.4 g (20 mmol) dimethylaminopyridine and 17.4 g a 50% solution of propanephosphonic anhydride (27.3 mmol) in Dichloromethane and then heated under reflux for 6 h. You drew that Solvens in vacuo, the residue was taken up in 300 ml of ethyl acetate and extracted twice with saturated sodium bicarbonate solution as well as each once with 5% citric acid solution, saturated sodium carbonate solution and saturated sodium chloride solution. The organic phase was over Dried magnesium sulfate and the solvent evaporated in vacuo. you received 4.8 g (95%) of N-tert-butyl-3-isopropylisopropylisothiazole-4,5-dicarboximide as a solid of mp. 52-53 ° C (Example No. 3.001).

N-tert-butyl-5-methyl-isoxazole-3,4-dicarboximide

To 3.8 g (16.8 mmol) of 3-tert-butylaminocarbonyl-5-methylisoxazole-4- carboxylic acid in 150 ml of dichloromethane was added dropwise at -5 ° C successively 6.3 g (62.2 mmol) of methylmorpholine, 2.4 g (20 mmol) of dimethylaminopyridine and 14.6 g of a 50% solution of propanephosphonic anhydride (23.0 mmol) in dichloromethane and then heated under reflux for 6 h. You drew that Solvens in vacuo, the residue was taken up in 300 ml of ethyl acetate and extracted twice with saturated sodium bicarbonate solution as well as each once with 5% citric acid solution, saturated sodium carbonate solution and saturated sodium chloride solution. The organic phase was over Dried magnesium sulfate and the solvent evaporated in vacuo. you received 3.2 g (91%) of N-tert-butyl-5-methyl-isoxazole-3,4-dicarboximide Solid of mp. 48-50 ° C (Example No. 2.001).

Analogously, for example, further compounds be prepared with the general structures

wherein X is oxygen or sulfur, and for example R¹ is a radical from the group Q₁ to Q₁₀₄, R² is a radical from the group M₁ to M₁₄₅ and the radicals X, Q and M can be combined as desired.  

R¹ and R² may be, for example, the following radicals:

Verb.-Nr. R Q₁ H Q₂ F Q₃ Cl Q₄ methyl Q₅ ethyl Q₆ propyl Q₇ 1-methylethyl Q₈ butyl Q₉ 1-methylpropyl Q₁₀ 2-methylpropyl Q₁₁ 1,1-dimethylethyl Q₁₂ pentyl Q₁₃ 1-methylbutyl Q₁₄ 2-methylbutyl Q₁₅ 3-methylbutyl Q₁₆ 1,1-dimethylpropyl Q₁₇ 1,2-dimethylpropyl Q₁₈ 2,2-dimethylpropyl Q₁₉ cyclopropyl Q₂₀ cyclo-butyl Q₂₁ cyclo-pentyl Q₂₂ cyclo-hexyl Q₂₃ cyclo-heptyl Q₂₄ cyclo-octyl Q₂₅ 1-methyl-propyl cyclio Q₂₆ cyclo-propyl-methyl Q₂₇ 1- (cyclo-propyl) ethyl Q₂₈ chloromethyl Q₂₉ dichloromethyl Q₃₀ trichloromethyl Q₃₁ chlorodifluoromethyl Q₃₂ trifluoromethyl Q₃₃ pentafluoroethyl Q₃₄ difluoromethyl Q₃₅ 1-Chloroethyl Q₃₆ 2-chloroethyl Q₃₇ 1-methyl-1-chloroethyl Q₃₈ 1-methyl-2-chloroethyl Q₃₉ methoxymethyl Q₄₀ 1-Methylmethoxymethyl Q₄₁ 1-methyl-2-methoxyethyl Q₄₂ 1-Methylethoxymethyl Q₄₃ ethoxymethyl Q₄₄ ethenyl Q₄₅ 1-propenyl Q₄₆ 2-propenyl Q₄₇ 1-methylethenyl Q₄₈ 1-Ethylethenyl Q₄₉ 2-phenylethenyl Q₅₀ 1-butenyl Q₅₁ 2-butenyl Q₅₂ 3-butenyl

Verb.-Nr. R Q₅₃ 1-methyl-1-propenyl Q₅₄ 1-methyl-2-propenyl Q₅₅ 2-methyl-2-propenyl Q₅₆ 2-propynyl Q₅₇ methoxy Q₅₈ ethoxy Q₅₉ propoxy Q₆₀ 1-methylethoxy Q₆₁ butoxy Q₆₂ 1-methylpropoxy Q₆₃ 1,1-dimethylethoxy Q₆₄ methylthio Q₆₅ ethylthio Q₆₆ chlorodifluoromethoxy Q₆₇ trifluoromethoxy Q₆₈ trichloromethylthio Q₆₉ phenyl Q₇₀ 2-fluorophenyl Q₇₁ 3-fluorophenyl Q₇₂ 4-fluorophenyl Q₇₃ 2-chlorophenyl Q₇₄ 3-chlorophenyl Q₇₅ 4-chlorophenyl Q₇₆ 2-methylphenyl Q₇₇ 3-methylphenyl Q₇₈ 4-methylphenyl Q₇₉ 2-trifluoromethylphenyl Q₈₀ 3-trifluorophenyl Q₈₁ 4-trifluorophenyl Q₈₂ 2-methoxyphenyl Q₈₃ 3-methoxyphenyl Q₈₄ 4-methoxyphenyl Q₈₅ 2,4-dichlorophenyl Q₈₆ 2,4,6-trimethylphenyl Q₈₇ phenoxy Q₈₈ phenylthio Q₈₉ 2-chlorophenoxy Q₉₀ 3-chlorophenoxy Q₉₁ 4-chlorophenoxy Q₉₂ 2,4-dichlorophenoxy Q₉₃ benzyl Q₉₄ 2-chlorobenzyl Q₉₅ 3-chlorobenzyl Q₉₆ 4-chlorobenzyl Q₉₇ 2-fluorobenzyl Q₉₈ 3-fluorobenzyl Q₉₉ 4-fluorobenzyl Q₁₀₀ 2-thienyl Q₁₀₁ 3-thienyl Q₁₀₂ 2-pyridyl Q₁₀₃ 3-pyridyl Q₁₀₄ 4-pyridyl

Verb.-Nr. R M₁ methyl M₂ ethyl M₃ propyl M₄ 1-methylethyl M₅ butyl M₆ 1-methylpropyl M₇ 2-methylpropyl M₈ 1,1-dimethylethyl M₉ pentyl M₁₀ 1-methylbutyl M₁₁ 2-methylbutyl M₁₂ 3-methylbutyl M₁₃ 1,1-dimethylpropyl M₁₄ 1,2-dimethylpropyl M₁₅ 2,2-dimethylpropyl M₁₆ 1-ethylpropyl M₁₇ hexyl M₁₈ 1-methylpentyl M₁₉ 2-methylpentyl M₂₀ 3-methylpentyl M₂₁ 4-methylpentyl M₂₂ 1,1-dimethylbutyl M₂₃ 1,2-dimethylbutyl M₂₄ 1,3-dimethylbutyl M₂₅ 2,2-dimethylbutyl M₂₆ 2,3-dimethylbutyl M₂₇ 3,3-dimethylbutyl M₂₈ 1-ethylbutyl M₂₉ 2-ethylbutyl M₃₀ 1,1,2-trimethyl-propyl M₃₁ 1,2,2-trimethyl-propyl M₃₂ 1-ethyl-1-methylpropyl M₃₃ 1-ethyl-2-methylpropyl M₃₄ cyclopropyl M₃₅ cyclo-butyl M₃₆ cyclo-pentyl M₃₇ cyclo-hexyl M₃₈ cyclo-heptyl M₃₉ cyclo-octyl M₄₀ 1-methyl-cyclo-propyl M₄₁ cyclo-propyl-methyl M₄₂ 1- (cyclo-propyl) ethyl M₄₃ 1-methylcyclohexyl M₄₄ 1-ethylcyclohexyl M₄₅ cyclohexylmethyl M₄₆ 2-propenyl M₄₇ 1-methyl-2-propenyl M₄₈ 1,1-dimethyl-2-propenyl M₄₉ 2-propynyl M₅₀ 1-methyl-2-propynyl M₅₁ 1,1-dimethylpropynyl M₅₂ phenylmethyl

Verb.-Nr. R M₅₃ 1-methylphenylmethyl M₅₄ 1,1-dimethylphenylmethyl M₅₅ 2-phenylethyl M₅₆ 2-methylthioethyl M₅₇ 1-methyl-2-methylthioethyl M₅₈ 1,1-dimethyl-2-methylthioethyl M₅₉ 3-methylthiopropyl M₆₀ 2-fluoroethyl M₆₁ 2-fluoro-1-methylethyl M₆₂ 1,1-dimethyl-2-fluoroethyl M₆₃ 2-chloroethyl M₆₄ 2-chloro-1-methylethyl M₆₅ 2-chloro-1,1-dimethylethyl M₆₆ 2-methoxyethyl M₆₇ 2-methoxy-1-methylethyl M₆₈ 1,1-dimethyl-2-methoxyethyl M₆₉ 3-methoxypropyl M₇₀ 2-cyanoethyl M₇₁ 2-cyano-1-methylethyl M₇₂ 2-cyano-1,1-dimethylethyl M₇₃ dimethylamino M₇₄ diethylamino M₇₅ morpholino M₇₆ piperidino M₇₇ phenyl M₇₈ 2-methylphenyl M₇₉ 3-methylphenyl M₈₀ 4-methylphenyl M₈₁ 2-ethylphenyl M₈₂ 3-ethylphenyl M₈₃ 4-ethylphenyl M₈₄ 2,3-dimethylphenyl M₈₅ 2,4-dimethylphenyl M₈₆ 2,5-dimethylphenyl M₈₇ 2,6-dimethylphenyl M₈₈ 3,4-dimethylphenyl M₈₉ 3,5-dimethylphenyl M₉₀ 2,3,4-trimethylphenyl M₉₁ 2,3,5-trimethylphenyl M₉₂ 2,4,5-trimethylphenyl M₉₃ 2,4,6-trimethylphenyl M₉₄ 3,4,5-trimethylphenyl M₉₅ 2-trifluoromethylphenyl M₉₆ 3-trifluoromethylphenyl M₉₇ 4-trifluoromethylphenyl M₉₈ 2-fluorophenyl M₉₉ 3-fluorophenyl M₁₀₀ 4-fluorophenyl m₁₀₁ 2-chlorophenyl M₁₀₂ 3-chlorophenyl M₁₀₃ 4-chlorophenyl M₁₀₄ 2,3-difluorophenyl

Verb.-Nr. R M₁₀₅ 2,4-difluorophenyl M₁₀₆ 2,5-difluorophenyl M₁₀₇ 2,6-difluorophenyl M₁₀₈ 2,3-dichlorophenyl M₁₀₉ 2,4-dichlorophenyl M₁₁₀ 2,5-dichlorophenyl M₁₁₁ 2,6-dichlorophenyl M₁₁₂ 2,3,4-trichlorophenyl M₁₁₃ 2,3,5-trichlorophenyl M₁₁₄ 2,4,6-trichlorophenyl M₁₁₅ 3,4,5-trichlorophenyl M₁₁₆ 2-cyanophenyl M₁₁₇ 3-cyanophenyl M₁₁₈ 4-cyanophenyl M₁₁₉ 2-methoxyphenyl M₁₂₀ 3-methoxyphenyl M₁₂₁ 4-methoxyphenyl M₁₂₂ 2,3-dimethoxyphenyl M₁₂₃ 2,4-dimethoxyphenyl M₁₂₄ 2,5-dimethoxyphenyl M₁₂₅ 2,6-dimethoxyphenyl M₁₂₆ 3,4-dimethoxyphenyl M₁₂₇ 3,5-dimethoxyphenyl M₁₂₈ 3,4,5-trimethoxyphenyl M₁₂₉ 2-trifluoromethoxyphenyl M₁₃₀ 3-trifluoromethoxyphenyl M₁₃₁ 4-trifluoromethoxyphenyl M₁₃₂ 2-nitrophenyl M₁₃₃ 3-nitrophenyl M₁₃₄ 4-nitrophenyl M₁₃₅ 2,3-dinitrophenyl M₁₃₆ 2,4-dinitrophenyl M₁₃₇ 2,5-dinitrophenyl M₁₃₈ 2,6-dinitrophenyl M₁₃₉ 3,4-dinitrophenyl M₁₄₀ 3,5-dinitrophenyl M₁₄₁ 1-naphthyl M₁₄₂ 2-naphthyl M₁₄₃ 3-tetrahydrofuryl M₁₄₄ 4-tetrahydropyranyl M₁₄₅ 2-thiazolyl

Table 1

Table 2

Table 3

applications

The herbicidal action of the dicarboxylic acid diimides of the formulas Ia and Ib was allowed show through greenhouse experiments:

The culture containers were plastic flowerpots with loamy sand and about 3.0% humus as substrate. The seeds of the test plants were sorted sown separately.

In pre-emergence treatment, those were suspended or emulsified in water Active ingredients directly after sowing by means of finely distributing nozzles applied. The jars were lightly rained to allow germination and growth promote and then covered with transparent plastic hoods, until the plants had grown. This cover causes a uniform Germination of the test plants, if not affected by the active substances has been.

For post-emergence treatment, the test plants were changed according to Growth forms only at a stature height of 3 to 15 cm with the in water treated suspended or emulsified active ingredients. The application rate for postemergence treatment was 2 kg / ha a. S.

The plants were species-specific at temperatures of 10-25 ° C or 20-35 ° C held. The trial period lasted for 2 to 4 weeks. During this time, the plants were maintained and their response to the individual treatments were evaluated.

The rating was based on a scale from 0 to 100. 100 means no Rising of the plants or complete destruction of at least the abovegrounds Parts and 0 no damage or normal growth.

The plants used in the greenhouse experiments took off following types together:

With 2.0 kg / ha a. S. used postemergence, can be with the Example 1.001 Combat broadleaf unwanted plants very well.

Claims (6)

1. dicarboximides of the formulas Ia and Ib in which the substituents have the following meaning:
X oxygen or sulfur;
R¹ is hydrogen; Halogen; C₁-C₆-alkyl which may carry one to five halogen atoms and / or one or two of the following radicals: cyclopropyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio or cyano ;
Phenyl or phenyl-C₁-C₄-alkyl, wherein the phenyl radical in each case unsubstituted or one to three times by C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio , C₁-C₆ haloalkylthio, halogen, cyano or nitro;
C₃-C₈cycloalkyl which is unsubstituted or substituted one to three times by C₁-C₄alkyl or halogen;
C₂-C₆-alkenyl, which may be substituted one to three times by halogen or C₁-C₃-alkoxy and / or once by phenyl, wherein the phenyl radical in turn may carry one to three of the following groups: C₁-C₄-alkyl, C₁- C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, cyano or nitro;
C₂-C₆-alkynyl, which may be substituted one to three times by halogen or C₁-C₃-alkoxy and / or once by phenyl, where the phenyl radical in turn may carry one to three of the following groups: C₁-C₄-alkyl, C₁- C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, cyano or nitro;
C₁-C₄ alkoxy; C₁-C₄-alkylthio; C₁-C₄-haloalkoxy; C₁-C₄-haloalkylthio;
Phenoxy or phenylthio which is unsubstituted or one to three times by C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, Cyano or nitro is substituted;
a 5- to 6-membered saturated or aromatic heterocyclic radical containing one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen which may carry one or two of the following substituents: C₁-C₃alkyl, halogen, C₁-C₃alkoxy and C₁-C₃ alkoxycarbonyl;
R² is hydrogen; hydroxyl; C₁-C₄ alkoxy;
C₁-C₆-alkyl which may carry one to three of the following groups: cyano, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁- C₄-haloalkylthio, di-C₁-C₄-alkylamino, halogen, C₃-C₈-cycloalkyl or phenyl, wherein the phenyl ring in turn can carry one to three of the following radicals: halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄ -Haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio or C₁-C₄-haloalkylthio;
C₃-C₈-cycloalkyl which may carry one to three of the following groups: C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, halogen, nitro or cyano;
C₃-C₆-alkenyl, which may be substituted one to three times by halogen and / or once by phenyl, wherein the phenyl radical in turn may carry one to three of the following groups: C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁- C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, cyano or nitro;
C₃-C₆-alkynyl which may be substituted one to three times by halogen and / or once by phenyl, wherein the phenyl radical in turn may carry one to three of the following groups: C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁- C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, cyano or nitro, may be substituted;
Di-C₁-C₄-alkylamino;
a 5- to 6-membered heterocyclic saturated or aromatic radical having one or two heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen, which may be substituted one to three times by C₁-C₄-alkyl or halogen;
Phenyl which may carry one to four of the following groups: C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, halogen, Nitro, cyano, formyl, C₁-C₄-alkanoyl, C₁-C₄-haloalkanoyl or C₁-C₄-alkoxycarbonyl;
Naphthyl, which may be substituted one to three times by C₁-C₄-alkyl or halogen,
and plant-tolerated salts of the dicarboxylic acid imides Ia and Ib, with the exception of 3-methylisoxazole-4,5-dicarboximide. 2. A process for the preparation of compounds of formulas Ia and Ib according to claim 1, characterized in that treated dicarboxylic acid monoamides of the formulas IIa, b or IIc, d in a conventional manner with dehydrating agents 3. A process for the preparation of the compounds Ia, characterized in that a hydroxamic acid chloride of the formula III in the presence of a base with halo-maleimides of the formula IV where R¹ and R² have the abovementioned meaning and Hal represents chlorine or bromine, is reacted. 4. A process for the preparation of the compounds Ia, characterized in that reacting a hydroxamic acid III III according to claim 3 in a conventional manner with maleimides V to the Isoxazolinimiden VI and then dehydrated with oxidizing agents. 5. A herbicidal composition containing a dicarboximide of the formula Ia or Ib according to claim 1, including 3-methylisoxazole-4,5-dicarboximide, as well as usual inert additives. 6. A method for controlling undesired plant growth, characterized that the unwanted plants and / or their Habitat with a herbicidally effective amount of at least one Dicarboxylic acid imides of the formula Ia or Ib or with 3-methylisoxazole 4,5-dicarboximide treated.