EP0746550A1

EP0746550A1 - Substituted triazolinones and their use as herbicides

Info

Publication number: EP0746550A1
Application number: EP95909695A
Authority: EP
Inventors: Karl-Heinz Linker; Kurt Findeisen; Wilhelm Haas; Otto Schallner; Heinz-Jürgen Wroblowsky; Markus Dollinger; Hans-Joachim Santel
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1994-02-22
Filing date: 1995-02-09
Publication date: 1996-12-11
Also published as: AU1808495A; DE4405614A1; HU9602306D0; PL315970A1; BR9506928A; CN1150421A; CA2183641A1; JPH09509923A; WO1995022532A1

Abstract

New substituted triazolinones have the general formula (I), in which Q stands for oxygen or sulphur, R<1> stands for halogen alkyl, R<3> stands for hydrogen or halogen, R<4> stands for cyano or nitro, R<2> stands for hydrogen or various substituents and R<5> stands for various substituents. Also disclosed are methods for producing these triazolinones and their use as herbicides.

Description

SUBSTITUTED TRIAZOLINONES AND THEIR USE AS HERBICIDES

The invention relates to new substituted triazolinones, processes for their preparation and their use as herbicides.

It is known that certain substituted triazolinones, such as the compound 2- (4-cyano-2,5-difluorophenyl) -5-methyl-4-propargyl-2,4-dihydro-3H-l, 2,4 triazol-3-one, have herbicidal properties (cf. EP-A 370332).

However, the action of these known compounds is not satisfactory in all respects.

The new substituted triazolinones of the general formula (I) have now been found

in which

Q represents oxygen or sulfur,

R ^{1 represents} haloalkyl,

R ^ stands for hydrogen, amino, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylidenimino or for optionally substituted cycloalkyl or cycloalkylalkyl,

R ^{J represents} hydrogen or halogen,

R ^{4 represents} cyano or nitro, and stands for isocyano, thiocyanato, sulfo, halosulfonyl, alkylaminooxy, dialkylaminooxy, alkylideneaminooxy, cycloalkylideneaminooxy, for optionally substituted cycloalkenyloxy or heterocyclyloxy, or for one of the following groups linked via nitrogen or oxygen

-NR ⁶ R ⁷ , -N = CR ⁸ R ⁹ , -O-CO-R ¹⁰ , -O-CS-R ¹⁰ , -O-CHR ^π -P (O) (OR ¹² ) ₂ , where

R ^{6 represents} hydrogen, in each case optionally substituted by halogen, alkyl, alkenyl or alkynyl, or the grouping -CO- R ¹³ , in which

R ¹³ for hydrogen, each optionally by halogen or

Alkoxy substituted alkyl or alkoxy, for amino, alkylamino or dialkylamino, or for each optionally substituted

Cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclylalkyl,

R ^{7 represents} the grouping - (CO) _n -R ¹³ , wherein

R ^{13 has} the meaning given above and

n represents the numbers 1 or 2,

R ^{8 represents} hydrogen, alkyl or alkoxy,

R ^{9 represents} alkoxy, alkylamino or dialkylamino,

R ^{10 represents} alkyl optionally substituted by halogen, alkoxy, alkylamino, dialkylamino or optionally substituted aryl,

R ¹¹ for each optionally substituted by halogen alkyl or cycloalkyl or for each optionally substituted aryl or

Heterocyclyl stands, and R ^{12 represents} alkyl.

Furthermore, it was found that the new substituted triazolinones of the general formula (I) can be obtained if

(a) aminoaryltriazolinones of the general formula (II)

in which

Q, R ¹ , R ² , R ³ , R ⁴ and R ^{6 have} the meanings given above,

with acid halides of the general formula (HI)

X ¹ - (CO) _n -R ¹³ (HI) in which

n and R ^{13 have} the meaning given above and

X ^{1 represents} halogen,

or with orthoesters of the general formula (IV)

R ⁸ -C (OR ⁹ ) ₃ (IV) in which

R ⁸ and R ^{9 have} the meanings given above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or if you

(b) hydroxyaryltriazolinones of the general formula (V)

in which

Q, R ¹ , R ² , R ³ and R ^{4 have} the meanings given above,

with acid halides of the general formula (VI)

X ² -CO-R ¹⁰ (VI) in which

R ^{10 has} the meaning given above and

X ^{2 represents} halogen,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,

or if you

(c) haloaryltriazolinones of the general formula (VII)

in which

Q, R ¹ , R ² , R ³ and R ^{4 have} the meanings given above and

X ^{3 represents} halogen,

with hydroxyalkylphosphonic acid esters of the general formula (VTII)

HO-CHR ^π -P (O) (OR ¹² ) ₂ (VIII) in which

R ¹¹ and R ^{12 have} the meanings given above,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent.

Finally, it was found that the new substituted triazolinones of the general formula (I) have interesting herbicidal properties.

Surprisingly, the substituted triazolinones of the general formula (I) according to the invention show a considerably better herbicidal activity against problem weeds in comparison with the substituted triazolinones known from the prior art, such as, for example, the compound 2- (4-cyano-2,5-difluorophenyl) ) -5-methyl-4-propargyl-2,4-dihydro-3H-l, 2,4-triazol-3-one.

The invention preferably relates to compounds of the formula (I) in which

Q represents oxygen or sulfur, R ^{1 represents} straight-chain or branched haloalkyl with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine or iodine,

R ² for hydrogen, amino, cyano, for straight-chain or branched alkyl having 1 to 8 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each with 2 to 6 carbon atoms, for straight-chain saturated or branched haloalkyl with 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine or iodine - for each straight-chain or branched haloalkenyl or haloalkynyl each with 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms - in particular

Fluorine, chlorine, bromine or iodine, for straight-chain or branched alkoxyalkyl each having 1 to 4 carbon atoms in the individual alkyl parts, for straight-chain or branched alkylideneimino having 1 to 8 carbon atoms or for each in the cycloalkyl part, in one or more cases, the same or different from halogen - especially fluorine,

Chlorine, bromine and / or iodine-substituted cycloalkyl or cycloalkylalkyl each having 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part,

R ^{3 represents} hydrogen, fluorine, chlorine, bromine or iodine,

R ^{4 represents} cyano or nitro, and

R ⁵ for isocyano, thiocyanato, sulfo, halosulfonyl, C _j -Cg alkylaminooxy, di (C _] -C ₄ alkyl) aminooxy, C _ι -C ₆ alkylidene aminooxy or C ₅ -C ₆ cycloalkylidene aminooxy, for each optionally by halogen, or C _] -C ₄ alkoxy-substituted C ₅ -C ₆ cycloalkenyloxy, perhydrofuranyloxy or perhydropyranyloxy, or for one of the following groups bonded via nitrogen or oxygen

-NR ⁶ R ⁷ , -N = CR ⁸ R ⁹ , -O-CO-R ¹⁰ , -O-CS-R ¹⁰ , -O-CHR ^π -P (O) (OR ¹ ) ₂ , where R ^{6 is} for Hydrogen, for each optionally by fluorine and / or

Chlorine-substituted alkyl, alkenyl or alkynyl each having up to 6 carbon atoms or for the grouping -CO-R ¹³ , in which

R ¹³ for hydrogen, each optionally by fluorine,

Chlorine or C _j -C ₄ alkoxy substituted alkyl or alkoxy each having 1 to 6 carbon atoms, for amino, for

Alkylamino or dialkylamino, each with 1 to 6 carbon atoms Share atoms in the alkyl, or for each optionally substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C _r C ₄ -alkyl, phenyl, naphthyl, phenyl-C _r C ₄ -alkyl, furyl , Thienyl or pyridyl, where in each case the following are suitable as substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 up to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximino-alkyl each having 1 to 4 carbon atoms in the individual alkyl parts and optionally single or multiple, identical or different, by halogen and / or straight chain or branched alkyl or alkoxy each having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1 to 9 identical or different

Halogen atoms substituted phenyl;

R ^{7 represents} the grouping - (CO) _n -R ¹³ , wherein

R ^{13 has} the meaning given above as preferred and n represents the numbers 1 or 2,

R ⁸ for hydrogen or for alkyl or alkoxy each with 1 to 6

Carbon atoms,

R ^{9 represents} alkoxy, alkylamino or dialkylamino, each having 1 to 6 carbon atoms in the alkyl groups,

R ¹⁰ for optionally substituted by fluorine and / or chlorine alkyl having 1 to 6 carbon atoms, for alkoxy or alkylamino or

Dialkylamino, each with 1 to 6 carbon atoms in the

Represents alkyl groups or optionally substituted phenyl, where the phenyl substituents indicated as preferred above under R ⁶ are also preferred here,

R ^{11 is} in each case optionally substituted by fluorine and / or chlorine alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms or in each case optionally substituted

Phenyl, naphthyl, furyl, thienyl or pyridyl, where the phenyl substituents given above as preferred under R ^{6 are also} preferred and

R ^{12 represents} alkyl having 1 to 6 carbon atoms.

The invention relates in particular to compounds of the formula (I) in which

Q represents oxygen or sulfur,

R ^{1 represents} straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine, bromine or iodine,

R ² for hydrogen, amino, cyano, for straight-chain or branched alkyl having 1 to 4 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each having 3 to 4 carbon atoms, for straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - especially fluorine or chlorine - for each straight-chain or branched haloalkenyl or haloalkynyl each with 3 to 4 carbon atoms and 1 to 5 identical or different halogen atoms - especially fluorine or chlorine - for straight-chain or branched alkoxyalkyl each with 1 to 3 carbon atoms in the individual alkyl parts, for straight-chain or branched alkylidene imino with 1 to 4 carbon atoms or for each optionally in the cycloalkyl part singly or repeatedly, identically or differently by halogen - in particular fluorine or chlorine - substituted cycloalkyl or cycloalkylalkyl each having 3 b is 6 carbon atoms in the cycloalkyl part and optionally 1 to 3 carbon atoms in the straight-chain or branched alkyl part, R ^{3 represents} hydrogen, fluorine or chlorine,

R ^{4 represents} cyano or nitro, and

R ⁵ for isocyano, thiocyanato, sulfo, chlorosulfonyl, C ₁ -C ₄ alkylaminooxy,

Di- C _j -C ₈ alkyl aminooxy, C _j -C ^ alkylidene aminooxy, C ₅ -C ₆ cycloalkylidene aminooxy, C ₅ -C ₆ cycloalkenyloxy, tetrahydrofuranyloxy, perhydropyranyloxy, or for one of the following about nitrogen or oxygen bound groups

R ^{6 represents} hydrogen, optionally substituted by fluorine-substituted alkyl having 1 to 4 carbon atoms or the grouping -CO-R ¹³ , in which

R ¹³ for hydrogen, for in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy alkyl or alkoxy each having 1 to 4 carbon atoms, for amino, for alkylamino or dialkylamino each with 1 to 4 carbon atoms in the alkyl parts, or for each counter ¬ also substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, phenyl, benzyl, phenylethyl, furyl, thienyl or

Pyridyl is available, the following being suitable as substituents:

Fluorine, chlorine, bromine, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfmyl or haloalkylsulfonyl each having 1 to 4 Carbon atoms and 1 to 9 identical or different halogen atoms - especially fluorine and / or chlorine atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl, each with 1 to 4 carbon atoms in the individual alkyl parts and optionally single or multiple, identical or different by fluorine, chlorine, bromine and / or straight-chain or branched alkyl or alkoxy each having 1 to 4 carbon atoms and / or straight-chain or branched

Haloalkyl or haloalkoxy, each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in particular fluorine and / or chlorine atoms, substituted phenyl;

R ^{7 represents} the grouping - (CO) _n -R ¹³ , wherein

R ^{13 has} the meaning given above as being particularly preferred and

n represents the numbers 1 or 2,

R ^{8 represents} hydrogen or alkyl or alkoxy each having 1 to 4 carbon atoms,

R ^{9 represents} alkoxy, alkylamino or dialkylamino each having 1 to 4 carbon atoms in the alkyl groups,

R ¹⁰ for optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms, for alkoxy or alkylamino or dialkylamino, each having 1 to 4 carbon atoms in the

Represents alkyl groups or optionally substituted phenyl, the phenyl substituents specified as particularly preferred above under R also being preferred here,

R ^{11 is} in each case optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6

Carbon atoms or represents in each case optionally substituted phenyl, naphthyl, furyl, thienyl or pyridyl, with the phenyl substituents specified above as being particularly preferred under R also being preferred here R ^{12 represents} alkyl having 1 to 4 carbon atoms.

The general definitions given above or those specified in preferred ranges apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation.

These radical definitions can be combined with one another as desired, that is to say also between the specified ranges of preferred compounds.

If, for example, 2- (5-amino-4-cyano-2-fluorophenyl) -5-difluoromethyl-4-methyl-2,4-dihydro-3H- is used to carry out process (a) according to the invention, l, 2,4-triazol-3-one and dichloroacetyl chloride as starting materials, the course of the reaction can be outlined using the following formula:

If, for example, 2- (2-chloro-4-cyano-5-hydroxyphenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H- is used to carry out process (b) according to the invention, l, 2,4-triazol-3-thione and chloroformic acid ethyl ester as starting materials, the course of the reaction can be outlined by the following film scheme:

For example, 2- (2,5-difluoro-4-nitro-phenyl) -5-dichloromethyl-4-difluoromethyl-2,4-dihydro-3H-1,2,4 is used to carry out process (c) according to the invention -triazol-3-one and hydroxymethane-phosphonic acid diethyl ester as starting materials, the course of the reaction can be outlined using the following formula:

HO-CH, -P (0) (OC ₂ 2H '' ₅ 5) / 2,

Formula (II) provides a general definition of the aminoaryltriazolinones to be used as starting materials in process (a) according to the invention for the preparation of the compounds of the general formula (I). In the formula (II), Q, R ¹ , R ² , R ³ , R ⁴ and R ⁶ preferably or in particular have those meanings which have already been described as preferred or in connection with the description of the compounds of the formula (I) as particularly preferred for Q, R ¹ , R ² , R ³ , R ⁴ and R ⁶ .

The starting materials of formula (II) are not yet known from the literature; however, they are the subject of older, not previously published patent applications.

The aminoaryltriazolinones of the general formula (II) are obtained if halogenaryltriazolinones of the general formula (VIII) - above - are reacted with ammonia, if appropriate in the presence of a diluent such as dimethyl sulfoxide, at temperatures between 0 ° C. and 150 ° C. (cf. the manufacturing examples). The acid halides to be used further as starting materials in process (a) according to the invention are generally defined by the formula (III)

1 -X defined. In the formula (II), n and R preferably or in particular have those meanings which have already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for n and R ¹³ ;

X ¹ preferably represents fluorine, chlorine or bromine, especially chlorine.

The starting materials of the formula (LU) are known organic synthetic chemicals.

Formula (IV) provides a general definition of the orthoesters to be used further as starting materials in process (a) according to the invention. In formula (IV), R ⁸ and R ⁹ preferably or in particular have those meanings which have already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R ⁸ and R ⁹ were.

The starting materials of the formula (IV) are known organic synthetic chemicals.

Formula (V) provides a general definition of the hydroxyaryltriazolinones to be used as starting materials in process (b) according to the invention for the preparation of the compounds of the general formula (I). In formula (V), Q, R ¹ , R ² , R ³ and R ⁴ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Q, R ¹ , R ² , R ³ and R ^{4 have been} given.

The starting materials of the formula (V) are not yet known from the literature; however, they are the subject of an older, unpublished patent application (cf. DE-P 4238125 / LeA 29445 of November 12, 1992).

The hydroxyaryltriazolinones of the general formula (V) are obtained if alkoxyaryltriazolinones of the general formula (IX)

in which

Q, R ¹ , R ² , R ³ and R ^{4 have} the meanings given above and

R represents alkyl (preferably methyl or ethyl),

with a dealkylating agent, e.g. Boron (III) bromide, in the presence of a diluent, e.g. Methyl enchloride, reacted at temperatures between 0 ° C and 50 ° C and processed in the usual way (cf. the manufacturing examples).

Formula (VI) provides a general definition of the acid halides to be used further as starting materials in process (b) according to the invention. In the formula (VI), R ¹⁰ preferably or in particular has the meaning which has already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R ¹⁰ ;

X ² preferably represents fluorine, chlorine or bromine, especially chlorine.

The starting materials of the formula (VI) are known organic synthetic chemicals.

Formula (VII) provides a general definition of the haloaryltriazolinones to be used as starting materials in process (c) according to the invention for the preparation of the compounds of the general formula (I). In formula (VII), Q, R ¹ , R ² , R ³ and R ⁴ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Q, R ¹ , R ² , R ³ and R ^{4 have been} given; X ³ preferably represents fluorine or chlorine, in particular fluorine.

The starting materials of formula (VII) are not yet known from the literature; however, they are the subject of an older, unpublished patent application.

The haloaryltriazolinones of the general formula (VII) are obtained if triazolinones of the general formula (X)

in which

Q, R ¹ and R ^{2 have} the meanings given above,

with halogen arenes of the general formula (XI)

in which

R ³ , R ⁴ and R ^{5 have} the meanings given above and

X ^{4 represents} halogen, preferably fluorine or chlorine, in particular fluorine, in the presence of a diluent, such as, for example, dimethyl sulfoxide and in the presence of an acid acceptor, such as, for example, potassium carbonate, at temperatures between 0 ° C. and 150 ° C. and to conventional Worked up way (see. The manufacturing examples). Formula (VIII) provides a general definition of the hydroxyalkylphosphonic acid esters to be used further as starting materials in process (c) according to the invention. In the formula (VLII), R ¹¹ and R ¹² preferably or in particular have those meanings which have already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R ¹¹ and R ¹² .

The starting materials of the formula (VHI) are known organic synthetic chemicals.

The usual organic solvents are suitable as diluents for carrying out processes (a), (b) and (c) according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. As such, all customary inorganic or organic bases are suitable for the reaction with the acid halides of the formula (III). These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide , Ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and basic organic nitrogen Compounds such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

Acidic catalysts are generally used as reaction aids for the reaction with the orthoesters of the formula (IV). Strong protonic acids such as e.g. Hydrochloric acid or hydrogen chloride, sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.

The reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 10 ° C and 100 ° C.

Process (a) according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out process (a) according to the invention, the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess. The reactions are generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is stirred for several hours at the temperature required in each case. Working up in the process according to the invention is carried out in each case by customary methods (cf. the production examples).

Processes (b) and (c) according to the invention are preferably carried out in the presence of a suitable acid acceptor. All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium ¬ hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, Ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and basic organic nitrogen compounds, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO) , Diazabicyclonones (DBN) or diazabicycloundecen (DBU).

The reaction temperatures can be varied within a substantial range when carrying out processes (b) and (c) according to the invention. In general, temperatures between 0 ° C and 100 ° C, preferably at temperatures between 10 ° C and 80 ° C.

Processes (b) and (c) according to the invention are generally carried out under normal conditions. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out processes (b) and (c) according to the invention, the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the temperature required in each case. Working up in the process according to the invention is carried out in each case by customary methods (cf. the preparation examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in the following plants: Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasumirumum, Scalumumum, Scalumumum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium. However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.

Depending on the concentration, the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.

The compounds of formula (I) according to the invention are particularly suitable for the selective control of monocot and dicot weeds in monocot and dicot crops, such as. For example, in wheat and barley both in the pre-emergence and in the post-emergence process. To a certain extent, the compounds of the formula (I) also show fungicidal activity, for example against pyricularia oryzae, phytophthora infestans and venturia inaequalis.

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

The following are suitable as solid carriers:

e.g. ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as Calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known herbicides for combating weeds, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids, such as, for example, di chlorpi colinic acid, dicamba and picloram; Aryloxyalkanoic acids, such as, for example, 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides, such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines such as oryzalin, pendimethalin and trifluralin; Diphenyl ethers such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; Ureas, such as chlorine toluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones such as imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles such as bromoxynil, dichlobenil and ioxynil; Oxyacetamides such as mefenacet; Sulfonylureas such as amidosulfuron, bensulfüron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines, such as, for example, atrazine, cyanazine, simazine, simetryne, terbutryne and terbutylazine; Triazinones such as hexazinone, metamitron and metribuzin; Others such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below. Manufacturing examples:

example 1

(Method (a))

3.15 g (0.01 mol) of 2- (2-fluoro-4-cyano-5-aminophenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-l, 2,4- triazol-3-one are placed in 50 ml of acetonitrile with 1.01 g (0.01 mol) of triethylamine and 1.21 g (0.01 mol) of trimethylacetic acid chloride are added with stirring, 5 hours at room temperature (20 ° C. ) stirred and concentrated. The residue is stirred with water, suction filtered and purified over a silica gel (mobile phase: cyclohexane / ethyl acetate 3: 1).

1.7 g (43% of theory) of 2- [2-fluoro-4-cyano-5- (tert-butylcarbonylamino) phenyl] -4-ethyl-5-trifluoromethyl-2,4 are obtained -dihydro-3H-l, 2,4-triazol-3-one with a melting point of 149 ° C.

Example 2

(Method (a))

3.15 g (0.01 mol) of 2- (2-fluoro-4-cyano-5-aminophenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-l, 2,4- triazol-3-one with 0.01 g of p-toluenesulfonic acid in 20 ml Triethyl orthoformate was stirred at reflux temperature for 20 minutes. The cooled solution is concentrated and recrystallized from a little isopropanol.

2 g (54% of theory) of 2- (2-fluoro-4-cyano-5-ethoxymethyleneaminophenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1, 2,4- triazol-3 -one with melting point 9FC.

Example 3

(Method (b))

2 g (0.007 mol) of 2- (2-fluoro-4-cyano-5-hydroxy-phenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-l, 2,4-triazole-3- on in 50 ml of acetonitrile with 0.23 g (0.0077

Mol) sodium hydride (80% in paraffin) added, stirred for 20 minutes at 20 ° C; 0.84 g (0.0077 mol) of ethyl chloroformate are then added and the mixture is stirred for 8 hours at room temperature (20 ° C.). After the concentration is with

Stirred water, acidified with concentrated hydrochloric acid, extracted three times with dichloromethane, the organic phase dried over sodium sulfate and concentrated. For purification, chromatography on silica gel (mobile phase: cyclohexane / ethyl acetate 1: 1).

0.8 g (32% of theory) of 2- [2-fluoro-4-cyano-5- (ethoxycarbonyloxy) phenyl] -4-methyl-5-difluoromethyl-2,4-dihydro-3H- 1, 2,4-triazol-3-one as an oil.

1H NMR (CDC1 ₃ ): 3.50; 4.35-4.43; 7.55-7.58 ppm Example 4

(Method (c))

6.3 g (0.03 mol) of diethyl 1-hydroxy-iso-butylphosphonate are mixed with 0.9 g (0.03 mol) of sodium hydride (80% in paraffin) in 100 ml of acetonitrile and at 20 ° for 20 minutes C stirred. After adding 3.15 g (0.01 mol) of 2- (2,5-difluoro-4-cyanophenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazole -3-one are stirred for 12 hours at room temperature (20 ° C). The mixture is stirred with water, the precipitated product is filtered off with suction and recrystallized from cyclohexane.

3 g (59% of theory) of 2- [2-fluoro-4-cyano-5- (l-diethoxyphosphoryl-isobutoxyphenyl] -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H are obtained - 1, 2,4-triazol-3-one with a melting point of 113 ° C.

Analogously to Examples 1 to 4 and in accordance with the general description of the production processes according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in Table 1 below.

Table 1: Examples of the compounds of the formula (I)

Ex. - R ¹ R ² R ³ R ⁴ R ⁵ Q physical

No properties

5 CF ₃ CH ₃ F CN NH-CO-C ₂ H ₅ O mp: 132 ° C 6 CF, C ₂ H ₅ F CN 7 ° C

CF, CH ₃ F CN CH, Mp .: 123 ° C

COCF ₃

8 CF ₃ C ₂ H ₅ F CN NH-COCF ₃ O mp .: 146 ° C 9 CF ₃ CH, F CN NH-COCH, O mp .: 155 ° C 10 CF, CH, CN NH-COCH (CH ₃ ) ₂ O 1H NMR (CDC1 ₃ , δ): = 1.14; 2.67; 3.36; 7.81; 8.15; 10.27

Ex- R ¹ R ^ R ^ά R ⁴ R physical

No properties

11 CF ₃ C ₂ H ₅ F CN NH-COCOC (CH ₃ ) ₃ O mp .: 176 ° C 12 CF ₃ C ₂ H ₅ F CN NH-CO-NH ₂ O mp:> 250 ° C 13 CF, CH, CN, CH ₃ s 1H NMR (CDC1 ₃ , δ): 3.36 3.70

COCF,

14 CF, CH, CN N (COCH ₃ ) ₂ O 1 H NMR (CDCI ₃ , δ): 2.27; 3.38; 8.06; 8.38

15 CF ₃ C ₂ H ₅ F CN NH-COCH ₃ O mp: 169 ° C 16 CF, C ₂ H ₅ F CN CH, O 1H-NMR (CDC1 ₃ , / ³ NH-COCH δ): 1.85 -1.8; 3.90 \

CI 3.98; 8.93-8.9

17 CF ₃ C ₂ H ₅ F CN NH-COC (CH ₃ ) ₂ CH ₂ Cl O m.p .: 149 ° C 18 CF ₃ C ₂ H ₅ F CN NH-COCH ₂ -Cl O m.p .: 121 ° C 19 CF, C ₂ H ₅ F CN N (COCH ₃ ) ₂ O mp: 112 ° C (dec.)

21 CHF ₂ CH ₃ F CN NH-CO-NH ₂ O 22 CHF-, CH, F NO ₂ N (COCH ₃ ) ₂ O 23 CF, CH, F NO ₂ NH-COC (CH ₃ ) ₃ O

Ex, R ¹ R ^ R ^ό R ⁴ R ⁵ physical

No properties

24 CHF ₂ CH ₃ F CN N = CH-OC ₂ H ₅ O mp .: 149 ° C 25 CF ₃ C ₂ H ₅ F CN CH, O 1H-NMR (CDC

_N δ): 1.95; 3.90-3

OC ₂ H ₅ 7.12-7.15

26 CF ₃ C ₂ H ₅ F CN N = C (OCH ₃ ) ₂ O mp .: 139 ° C 27 CF ₃ C ₂ H ₅ F CN N-CH-N (CH ₃ ) ₂ O 28 CF ₃ CH ₃ CI CN N = C (OCH ₃ ) ₂ O 29 CF ₃ CH ₃ F CN N = C (OC ₂ H ₅ ) ₂ s 30 CF ₃ C ₂ H ₅ F NO ₂ N = CH-OC ₂ H ₅ O 31 CHF, CH, F CN CH,

/ s

OC ₂ H ₅

32 CF ₃ C ₂ H ₅ F CN -OCOOC ₂ H ₅ O 1H-NMR (CDC1 δ): 3.90-4.00; 4, 4.45; 7.58-7.60

33 CF ₃ CH ₃ F CN -OCOOCH ₂ -CH ₂ -Cl O

34 CHF ₂ CH ₃ CI CN -OCOOC ₂ H ₅ O

35 CF ₃ CH ₃ F NO ₂ -OCOO C ₂ H ₅ O

36 CF ₃ C ₂ H ₅ F CN -OCOOC ₂ H ₅ s

37 CF ₃ C ₂ H ₅ F CN -OCH ₂ -PO (OC ₂ H ₅ ) ₂ O mp: 89 ° C

Ex. - R ¹ R ^ R ^ά R ⁴ R> physical

No properties

38 CF ₃ CH ₃ F CN -OCH ₂ -PO (OC ₂ H ₅ ) ₂ O

39 CF ₃ CH ₃ F CN -OCH-PO (OC ₂ H ₅ ) ₂ O

CH,

40 CHF ₂ CH ₃ F CN -OCH-PO (OC ₂ H ₅ ) ₂ O

CH,

41 CF ₃ C ₂ H ₅ F CN -OCH-PO (θC ₂ H ₅ ) ₂ O mp: 90 ° C

CH,

44 CF ₃ C ₂ H ₅ F CN -OCH-PO (OC ₂ H ₅ ) ₂ O

46 CF ₃ CH ₃ F CN -NH-CO-C ₂ H ₅ O

47 CF ₃ C ₂ H ₅ F CN N = CH-N (CH ₃ ) ₂ O mp: 155 ° C Example R ¹ R * R ^ά R ⁴ R ⁵ Q physical

No properties

48 CF ₃ C ₂ H ₅ F CN NH-COOC ₂ H ₅ O m.p .: 112 ° C 49 CF ₃ C ₂ H ₅ F CN NH-COCOOC ₂ H ₅ O m.p .: 133 ° C 50 CF ₃ C ₂ H ₅ F CN NH-CHO O Mp .: 156 ° C 51 CF ₃ CH ₃ F NO ₂ NH-COCF ₃ O 52 CHF ₂ CH ₃ CI CN N (COCH ₃ ) ₂ O

54 CF ₃ CH ₃ F CN -SCN O ng ° = 1.5221 55 CF ₃ CH ₃ F CN -SO ₂ Cl O mp: 205 ° C

57 CF ₃ CH ₃ F CN -ON (C ₂ H ₅ ) ₂ s (amorphous) 58 CF, CH, F CN -ON (C ₂ H ₅ ) ₂ O mp .: 78 ° C 59 CF, CH, CN,

5.0; 5.85; 6.05;

7.75; 8.15

Ex - R ¹ R ² R ³ R ⁴ R ⁵ Q physical

No properties

62 CF ^■ 3, 3.70; 3.85; 4.75;

7.75; 8.2

63 CF ₃ CH ₃ F CN O mp: 128 ° C

64 CF ₃ CH ₃ F CN -OCS-N (CH ₃ ) ₂ O 1H-NMR (CDC1 ₃ , δ): 3.40; 3.45;

3.50;

7.52-7.60 ppm;

65 CF 3, C ^ 2, H ⁿ 5 _< F ^x C ^ N / CH " ₃ 3 O 1H-NMR (CDC1 ₃ ,

- N = C v δ): 1.95; 3.87; OCH,

3.90-

3.98 ppm

Starting materials of the formula (UV

Example (II-IV

9.54 g (0.03 mol) of 2- (2,5-difluoro-4-cyano-phenyl) -4-emyl-5-trifluoromethyl-2,4-dihydro-3H-l, 2,4-triazole- 3-one are heated to 120 ° C in 150 ml of dimethyl sulfoxide and ammonia gas is passed in for 20 hours. The cooled solution is stirred on ice water, the precipitated product is filtered off with suction, washed with water and the residue is recrystallized from isopropanol.

5.8 g (61% of theory) of 2- (2-fluoro-4-cyano-5-aminophenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2 are obtained. 4-triazol-3-one with a melting point of 193 ° C.

Starting materials of formula (V): Example (V-l)

4.95 g (0.015 mol) of 2- (2-fluoro-4-cyano-5-methoxy-phenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-l, 2,4-triazole- 3-one are placed in 200 ml of methylene chloride at 10 ° C. and a one-molar solution of 45 g (0.045 mol) of boron (III) bromide in methylene chloride is added dropwise. The reaction mixture is stirred at 20 ° C. for 12 hours and then 100 ml of water are added. After stirring for ten minutes, the organic phase is separated off, washed with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.

3.1 g (65% of theory) of 2- (2-fluoro-4-cyano-5-hydroxy-phenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2 are obtained. 4-triazol-3-one with a melting point of 195 ° C.

Starting materials of the formula (VIIV

Example (VII-l

To 5.3 g (0.032 mol) of 4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1, 2,4-triazol-3-one (see, for example, US Pat. No. 3,780,052) and 5.5 g (0.032 mol) of 5-chloro-2,4-difluorobenzonitrile in 100 ml of dimethyl sulfoxide, 5.3 g (0.038 mol) of potassium carbonate are added at room temperature and the mixture is then heated to 100 ° C. for 36 hours. For working up, the cooled reaction mixture is poured into water, brought to pH 2 with dilute hydrochloric acid and extracted several times with dichloromethane. The combined organic phases are dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel (mobile phase: dichloromethane).

1.8 g (18% of theory) of 2- (2-chloro-4-cyano-5-fluorophenyl) -4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2 are obtained. 4-triazolin-3-one with a melting point of 105 ° C.

Examples of use:

In the application examples, the following compound (A) is used as a reference substance:

2- (4-cyano-2,5-difluorophenyl) -5-methyl-4-propargyl-2,4-dihydro-3H-1,2,4-triazol-3-one (known from EP-A 370332 ).

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil and watered with the active compound preparation after 24 hours. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

0% = no effect (like untreated control) 100% = total destruction

A clear superiority in effectiveness compared to the prior art is shown in barley (0-10%) and wheat cultures (0%) in this test e.g. the compounds according to Preparation Examples 4, 13, 17, 25, 26, 37 and 41 against weeds such as Digitaria (80-95%), Abutilon (100%), Chenopodium (95-100%), Galinsoga (70-100%) , Matricaria (60-100%), Portulaca (70-100%), Solanum (80-100%) and Viola (80-100%).

Claims

1. New substituted triazolinones of the general formula (I)

in which

Q represents oxygen or sulfur,

R ^{1 represents} haloalkyl,

R ^{2 represents} hydrogen, amino, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkylideneimino or represents optionally substituted cycloalkyl or cycloalkylalkyl,

R ^{3 represents} hydrogen or halogen,

R ^{4 represents} cyano or nitro, and

R ^{5 stands} for isocyano, thiocyanato, sulfo, halosulfonyl, alkylaminooxy, dialkylaminooxy, alkylideneaminooxy, cycloalkylideneaminooxy, for optionally substituted cycloalkenyloxy or heterocyclicloxy, or for one of the following groups bonded via nitrogen or oxygen

-NR ⁶ R ⁷ , -N = CR ⁸ R ⁹ , -O-CO-R ¹⁰ , -O-CS-R ¹⁰ , -O-CHR ¹¹ - P (O) (OR ¹² ) ₂ , where R ^{6 is} for Hydrogen, for in each case optionally substituted by halogen alkyl, alkenyl or alkynyl, or for the

Grouping -CO-R ¹³ stands in which R ^{13 stands} for hydrogen, for alkyl or alkoxy optionally substituted by halogen or alkoxy, for amino, alkylamino or dialkylamino, or for optionally substituted cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclylalkyl,

R ^{7 represents} the grouping - (CO) _n -R ¹³ , wherein

R ^{13 has} the meaning given above and

n represents the numbers 1 or 2,

R ^{8 represents} hydrogen, alkyl or alkoxy,

R ^{9 represents} alkoxy, alkylamino or dialkylamino,

R ^{10 represents} alkyl which is optionally substituted by halogen, alkoxy, alkylamino, dialkylamino or optionally substituted aryl,

R ¹¹ for alkyl or cycloalkyl optionally substituted by halogen or for optionally substituted in each case

Aryl or heterocyclyl, and

R ^{12 represents} alkyl.

2. New substituted triazolinones of the general formula (I) according to

Claim 1, characterized in that

Q represents oxygen or sulfur,

R ^{1 represents} straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine or iodine,

R ² for hydrogen, amino, cyano, for straight-chain or branched alkyl having 1 to 8 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each having 2 to 6 carbon atoms, for straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine or iodine - for each straight-chain or branched haloalkenyl or

Haloalkynyl, each with 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms - in particular fluorine, chlorine, bromine or iodine - for straight-chain or branched alkoxyalkyl, each with 1 to 4 carbon atoms in the individual alkyl parts, for straight-chain or branched Alkylidenimino with 1 to

8 carbon atoms or for cycloalkyl or cycloalkylalkyl, each of which is mono- or polysubstituted in the cycloalkyl part, one or more times, identically or differently, by halogen - in particular fluorine, chlorine, bromine and / or iodine - each having 3 to 8 carbon atoms in the cycloalkyl part and optionally 1 to 4 Carbon atoms in the straight-chain or branched alkyl part,

R ^{3 represents} hydrogen, fluorine, chlorine, bromine or iodine,

R ^{4 represents} cyano or nitro, and

R ⁵ for isocyano, thiocyanato, sulfo, halosulfonyl, C ₁ -C ₆ alkylaminooxy, di (C ₁ -C ₄ alkyl) aminooxy, C ₁ -C ₆ alkylidene aminooxy or C ₅ -C ₆ cycloalkylidene aminooxy, represents in each case optionally substituted by halogen, C ₁ -C ₄ alkyl or CC ₄ alkoxy C ₅ -C ₆ cycloalkenyloxy, perhydrofuranyloxy or perhydropyranyloxy, or one of the following groups linked via nitrogen or oxygen

-NR ⁶ R ⁷ , -N = CR ⁸ R ⁹ , -O-CO-R ¹⁰ , -O-CS-R ¹⁰ , -O-CHR ¹¹ - P (O) (OR ¹² ) ₂ , where

R ⁶ for hydrogen, for each optionally substituted by fluorine and / or chlorine alkyl, alkenyl or alkynyl each having up to 6 carbon atoms or for

Grouping -CO-R ¹³ stands in which R ¹³ for hydrogen, for each optionally by

Fluorine, chlorine or C _j -C ₄ alkoxy-substituted alkyl or alkoxy each having 1 to 6 carbon atoms, for amino, for alkylamino or dialkylamino

5 each 1 to 6 carbon atoms in the alkyl parts, or for each optionally substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl-C _r C ₄ -alkyl, phenyl, naphthyl, phenyl-C ₁ -C ₄ - alkyl, furyl, thienyl or pyridyl, where in each case as a substituent in

10 question come:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms, each straight-chain or branched halo

15 genalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximino

20 alkyl with 1 to 4 carbon atoms in each of the individual alkyl parts and optionally single or multiple, identical or different by halogen and / or straight-chain or branched alkyl or alkoxy each having 1 to 4 carbon atoms

25 and / or straight-chain or branched haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms substituted phenyl;

R ^{7 represents} the grouping - (CO) _n -R ¹³ , wherein

30 R ^{13 has} the meaning given above as preferred and n represents the numbers 1 or 2, R ^{8 represents} hydrogen or alkyl or alkoxy each having 1 to 6 carbon atoms,

R ¹⁰ for optionally substituted by fluorine and / or chlorine

Alkyl with 1 to 6 carbon atoms, for alkoxy, alkylamino or dialkylamino or dialkylamino each with 1 to 6 carbon atoms in the alkyl groups or for optionally substituted phenyl, the phenyl substituents mentioned above as preferred under R ^{6 also} being preferred here come,

R ^{11 represents} in each case optionally substituted by fluorine and / or chlorine alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms or optionally substituted phenyl, naphthyl, furyl, thienyl or pyridyl, here too the phenyl substituents indicated as preferred above under R ⁶ are preferably suitable and

R ^{12 represents} alkyl having 1 to 6 carbon atoms.

New substituted triazolinones of the general formula (I) according to

Claim 1, characterized in that

Q represents oxygen or sulfur,

R ² for hydrogen, amino, cyano, for straight-chain or branched alkyl having 1 to 4 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each having 3 to 4 carbon atoms. atoms, for straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine or chlorine -, for each straight-chain or branched haloalkenyl or haloalkynyl each having 3 to 4 carbon atoms and 1 to 5 same or various halogen atoms - in particular fluorine or chlorine - for straight-chain or branched alkoxyalkyl each having 1 to 3 carbon atoms in the individual alkyl parts, for straight-chain or branched alkylidene imino having 1 to 4 carbon atoms or for each optionally in the cycloalkyl part single or multiple, identical or cycloalkyl or cycloalkylalkyl which is differently substituted by halogen - in particular fluorine or chlorine - each having 3 to 6 carbon atoms in the cycloalkyl part and optionally 1 to 3 carbon atoms in the straight-chain or branched alkyl part,

R ^{3 represents} hydrogen, fluorine or chlorine,

R ^{4 represents} cyano or nitro, and

R ⁵ is isocyano, thiocyanato, sulfo, chlorosulfonyl, C ^ _j alkyl aminooxy, di- (C ₁ -C ₃ alkyl) -aminooxy, C ₁ -C ₄ alkylidene-aminooxy, C ₅ -C ₆ -Cycloalkylidenaminooxy , C ₅ -C ₆ -cycloalkenyloxy, tetrahydrofuranyloxy, perhydropyranyloxy, or for one of the following groups bound via nitrogen or oxygen

R ^{6 represents} hydrogen, optionally fluorine-substituted alkyl having 1 to 4 carbon atoms or the grouping - CO-R ¹³ , in which

R ¹³ for hydrogen, each optionally substituted by fluorine, chlorine, methoxy or ethoxy Alkyl or alkoxy, each with 1 to 4 carbon atoms, for amino, for alkylamino or dialkylamino, each with 1 to 4 carbon atoms in the alkyl parts, or for optionally substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl , Cyclohexylmethyl, phenyl, benzyl, phenylethyl, furyl, thienyl or pyridyl, where in each case the following are suitable as substituents:

10 fluorine, chlorine, bromine, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkyl

15 thio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine and / or chlorine atoms, in each case straight-chain or branched alkoxycarbonyl or

20 alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and, if appropriate, single or multiple, the same or different by fluorine, chlorine, bromine and / or straight-chain or branched alkyl or alkoxy each having 1

25 to 4 carbon atoms and / or straight-chain or branched haloalkyl or haloalkoxy, each with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in particular fluorine and / or chlorine atoms

30 phenyl;

R stands for the grouping - (CO) _n -R, in which

R ^{13 has} the meaning given above as being particularly preferred and n represents the numbers 1 or 2,

R ^{8 represents} hydrogen or alkyl or alkoxy each having 1 to 4 carbon atoms,

R ^{10 represents} optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms, alkoxy, alkylamino or dialkylamino each having 1 to 4 carbon atoms in the alkyl groups or optionally substituted phenyl, the above under R ⁶ being particularly preferred added phenyl substituents are also preferred here,

R ^{11 represents} in each case optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms or optionally substituted phenyl, naphthyl, furyl, thienyl or pyridyl, here too the phenyl substituents specified as particularly preferred above under R ⁶ are preferably suitable and

R ^{12 represents} alkyl having 1 to 4 carbon atoms.

4. Process for the preparation of new substituted triazolinones of the general formula (I)

in which R ¹ , R ² , R ³ , R ⁴ , R ⁵ and Q have the meanings given in Claim 1,

characterized in that one

(a) aminoaryltriazolinones of the general formula (II)

in which

Q, R ¹ , R ² , R ³ , R ⁴ and R ^{6 have} the meanings given above,

with acid halides of the general formula (in)

X ¹ - (CO) _n -R ¹³ (m) in which

n and R ^{13 have} the meaning given above and

X ^{1 represents} halogen,

or with orthoesters of the general formula (IV)

R ⁸ -C (OR ⁹ ) ₃ (IV) in which

R ⁸ and R ^{9 have} the meanings given above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or that one (b) hydroxyaryltriazolinones of the general formula (V)

in which

Q, R ¹ , R ² , R ³ and R ^{4 have} the meanings given above,

with acid halides of the general formula (VI)

X ² -CO-R ¹⁰ (VI)

in which

R ^{10 has} the meaning given above and

X ^{2 represents} halogen,

optionally in the presence of an acid acceptor and optionally in

In the presence of a diluent,

or that one

(c) haloaryltriazolinones of the general formula (VII)

in which Q, R ¹ , R ² , R ³ and R ^{4 have} the meanings given above and

X ^{3 represents} halogen,

with hydroxyalkylphosphonic acid esters of the general formula (Vffl)

HO-CHR ^π -P (O) (OR ¹² ) ₂ (Vm) in which

R ¹¹ and R ^{12 have} the meanings given above,

5. Herbicidal agents, characterized in that they contain at least one substituted triazolinone of the general formula (I) according to Claims 1 to 5.

6. A method for controlling unwanted plants, characterized in that substituted triazolinones of the general formula (I) according to Claims 1 to 5 are allowed to act on plants and / or their habitat.

7. Use of substituted triazolinones of the general formula (I) according to Claims 1 to 5 for combating undesirable plants.

8. A process for the preparation of herbicidal compositions, characterized in that substituted triazolinones of the general formula (I) according to Claims 1 to 5 are mixed with extenders and / or surface-active substances.