WO1994009012A1

WO1994009012A1 - Substituted triazolinones

Info

Publication number: WO1994009012A1
Application number: PCT/EP1993/002705
Authority: WO
Inventors: Kurt Findeisen; Karl-Heinz Linker; Otto Schallner; Klaus-Helmut Müller; Klaus König; Hans-Joachim Santel; Robert R. Schmidt
Original assignee: Bayer Aktiengesellschaft
Priority date: 1992-10-12
Filing date: 1993-10-04
Publication date: 1994-04-28
Also published as: BR9307225A; AU5110693A; CA2146661A1; DE4234306A1; RU95113591A; AU664780B2; JPH08505837A; EP0663917A1

Abstract

The invention relates to novel substituted triazolinones of general formula (I) where Het is a heterocycle of formula (a) or (b) and R?1, R2, R3, A, X1, R4, R5, R6, R7 and X2¿ have the meanings given in the description, several processes for their production and their use as herbicides.

Description

Substituted triazolinones

The invention relates to new substituted triazolinones, several processes for their preparation and their use as herbicides. It is known that certain substituted triazolinones such as the compound 2-methyl-3-dimethylamino-l- [N- (2,2-dimethyl-1-propyl) aminocarbonyl] 1,2,4-triazolin-5-one have herbicidal properties (see, for example, EP 431 390).

However, the herbicidal activity of these previously known compounds against problem weeds, like their tolerance to important crop plants, is not entirely satisfactory in all fields of application.

New substituted triazolinones of the general formula (I)

in which

Het for a heterocycle of the formula or

stands,

R ¹ , R ² and R ³ each independently represent halogen, alkyl, alkenyl, alkynyl, alkoxy or optionally substituted arylalkyl, aryl or aryloxy,

A represents a doubly linked alkanediyl radical and χ ^{1 represents} oxygen or sulfur, where

R ⁴ for hydrogen, halogen, cyano, nitro, for optionally substituted

Alkyl, for alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxy,

Alkylthio, alkylsulfmyl, alkylsulfonyl, alkoxycarbonyl, represents in each case optionally substituted cycloalkyl, aryl or aryloxy or for a radical of the formula,

R ^{5 stands} for hydrogen, cyano, for optionally substituted alkyl, for alkenyl, alkynyl, alkoxy, alkoxycarbonyl, aminocarbonyl, for amino, N-alkylamino, N, N-dialkylamino, alkylidenimino or for optionally substituted cycloalkyl, aryl or aryloxy,

R ⁶ for alkyl, alkoxy, alkylthio or for a radical of the formula

stands,

R ^{7 represents} alkyl or cycloalkyl,

R ⁸ and R ⁹ either independently of one another each represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or each optionally substituted arylalkyl or aryl or together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle,

R ¹⁰ and R ^{1 1} either independently of one another in each case for alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl,

Alkoxy, cycloalkyl, cycloalkylalkyl, each represent optionally substituted aryl, arylalkyl or heteroaryl or together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle and X ^{2 represents} oxygen or sulfur, found.

Depending on the nature of the substituents, the compounds of the formula (I) can optionally be present as geometric and / or optical isomers or isomer mixtures of different compositions. Both the pure isomers and the isomer mixtures are claimed according to the invention.

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

in which

Het for a heterocycle of the formula of

stands,

R ¹ , R ² and R ³ each independently represent halogen, alkyl, alkenyl, alkynyl, alkoxy or optionally substituted arylalkyl, aryl or aryloxy, A represents a double-linked alkanediyl radical and χ ^{1 represents} oxygen or sulfur, where

R ⁴ for hydrogen, halogen, cyano, nitro, for optionally substituted alkyl, for alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkoxycarbonyl, for each ge optionally substituted cycloalkyl, aryl or aryloxy or represents a radical of the formula

R ⁶ for alkyl, alkoxy, alkylthio or for a radical of the formula

stands,

R ^{7 represents} alkyl or cycloalkyl, R ⁸ and R ⁹ either independently of one another each represent hydrogen, alkyl,

Are alkenyl, alkynyl, cycloalkyl or each optionally substituted arylalkyl or aryl or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, R ¹⁰ and R ^{1 1} either independently of one another each represent alkyl, alkenyl,

Alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkoxy, cycloalkyl, cycloalkylalkyl, each represent optionally substituted aryl, arylalkyl or heteroaryl or together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle and

X ^{2 represents} oxygen or sulfur is obtained if a) 1-chloro (thio) carbonyltriazolinones of the formula (II),

in which

Het and X ^{1 have} the meanings given above, with amines of the formula (III),

in which

R ¹ , R ² , R ³ and A have the meanings given above, if appropriate in Gregenwart, reacting a diluent and also in the presence of a reaction auxiliary, or if b) triazolinones of the formula (IV) which are unsubstituted in the 1-position,

Het-H (IV) in which

Het has the meaning given above, with iso (thio) cyanates of the formula (V),

in which R ¹ , R ² , R ³ , A and X ^{1 have} the meanings given above, if appropriate in Gregenwart of a diluent and if appropriate in the presence of a reaction auxiliary.

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

Surprisingly, the substituted triazolinones of the general formula (I) according to the invention show a considerably better herbicidal activity against problem weeds and, at the same time, significantly better tolerance to important crop plants in comparison to the substituted triazolinones known from the prior art, such as the compound 2-methyl-3- dimethylamino-1- [N- (2,2-dimethyl-1-propyl) aminocarbonyl] -1,2,4-triazolin-5-one, which are chemically and functionally obvious compounds.

Formula (I) provides a general definition of the substituted triazolinones according to the invention. Compounds of formula (I) are preferred in which

Het stands for a heterocycle of the formula or

R ¹ , R ² and R ³ independently of one another each for fluorine, chlorine, bromine, iodine, for straight-chain or branched alkyl having 1 to 8 carbon atoms, for straight-chain or branched alkenyl with 2 to 8 carbon atoms, for straight-chain or branched alkynyl with 2 to 8 carbon atoms, stand for straight-chain or branched alkoxy with 1 to 8 carbon atoms or for arylalkyl, aryl or aryloxy with 6 to 10 carbon atoms in the aryl part and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl part which are optionally mono- or polysubstituted in the same or different ways , the following being suitable as aryl substituents: Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or

Alkoximinoalkyl, each with 1 to 6 carbon atoms in the individual alkyl parts and optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms, phenyl, A stands for a double-linked alkanediyl radical with 1 to 8 carbon atoms and

X ^{1 represents} oxygen or sulfur, where

R ^{4 represents} hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro or straight-chain or branched, optionally mono- or polysubstituted, identically or differently substituted alkyl, the following being suitable as substituents:

Fluorine, chlorine, bromine, iodine, hydroxy, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N-dialkylamino, each having 1 to 8 carbon atoms in the individual alkyl parts;

R ⁴ also for each straight-chain or branched alkenyl or alkynyl each having 2 to 8 carbon atoms, 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 and / or iodine or for straight-chain or branched alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl each with 1 to 8 carbon atoms in stands for the individual alkyl parts, furthermore stands for cycloalkyl with 3 to 8 carbon atoms optionally substituted once or several times, identically or differently by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, and also stands for optionally optionally single or multiple times, The same or different substituted aryl or aryloxy each having 6 to 10 carbon atoms, the following being suitable as aryl substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts and, if appropriate, mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms, phenyl or R ^ represents a radical of the formula

R ^{5 represents} hydrogen, cyano, amino, aminocarbonyl or straight-chain or branched, optionally mono- or polysubstituted, identically or differently substituted alkyl having 1 to 8 carbon atoms, where as

Substituents are possible:

Fluorine, chlorine, bromine, iodine, hydroxy, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N-dialkylamino, each having 1 to 8 carbon atoms in the individual alkyl parts; R ⁵ also represents straight-chain or branched alkenyl or alkynyl each having 2 to 8 carbon atoms, each straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N, N-dialkylamino or alkylidenimino each having 1 to 8 carbon atoms in the individual alkyl parts, furthermore stands for cycloalkyl with 3 to 8 carbon atoms which is optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, and additionally for aryl or aryloxy which is monosubstituted or polysubstituted in the same or different manner each 6 to 10 carbon atoms, the following being suitable as aryl substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts and, if appropriate, mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms,

R ⁶ for each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 8 carbon atoms or for a radical of the formula

stands. R ^{7 represents} straight-chain or branched alkyl having 1 to 8 carbon atoms or cycloalkyl having 3 to 8 carbon atoms,

R ⁸ and R ⁹ are each independently of one another in each case for hydrogen, 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 8 carbon atoms, for cycloalkyl with 3 to 8 carbon atoms or for each optionally simple or arylalkyl or aryl which are substituted several times, identically or differently, each having 6 to 10 carbon atoms in the aryl part and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl part, the following being suitable as aryl substituents: halogen, cyano, nitro, in each case straight-chain or branched alkyl, Alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl, each having 1 to 6 carbon atoms in the individual alkyl parts and, if appropriate, singly or multiply, identically or differently, substituted by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms; or R ⁸ and R ⁹ together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally mono- or polysubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 4 carbon atoms and which, if appropriate, 1 up to 2 further heteroatoms - especially nitrogen,

Can contain oxygen or sulfur, and R ^{1 1} either independently of one another in each case 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 8 carbon atoms, for straight-chain or branched haloalkyl having 1 to 6 Carbon atoms and 1 to 13 identical or different halogen atoms - especially fluorine, chlorine, bromine and / or iodine - for each straight-chain or branched haloalkenyl or haloalkynyl each with 2 to 6 carbon atoms and 1 to 1 1 identical or different halogen atoms - especially fluorine, chlorine , Bromine and / or iodine, for each straight-chain or branched

Alkoxyalkyl or alkoxy, each with 1 to 8 carbon atoms in the individual alkyl parts, for cycloalkyl with 3 to 8 carbon atoms, for cycloalkylalkyl with 3 to 8 carbon atoms in the cycloalkyl part and 1 to 6 carbon atoms in the straight-chain or branched alkyl part, for each optionally one or more times the same or variously substituted

Aryl or arylalkyl each having 6 to 10 carbon atoms in the aryl part and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl part or for heteroaryl with 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms which are optionally mono- or polysubstituted identically or differently - in particular nitrogen ,

Oxygen and / or sulfur are available, aryl and heteroaryl substituents being suitable: Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 6 carbon atoms in the individual alkyl parts and optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms; or R ¹⁰ and R ^{1 1} together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which may or may not be mono- or polysubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 4 carbon atoms Can contain 1 to 2 further heteroatoms - in particular nitrogen, oxygen and / or sulfur - and

X ^{2 represents} oxygen or sulfur.

Compounds of the formula (I) in which

Het stands for a heterocycle of the formula or

R ¹ , R ² and R ³ independently of one another each represent fluorine, chlorine, bromine, for straight-chain or branched alkyl having 1 to 6 carbon atoms, for straight-chain or branched alkenyl having 2 to 6 carbon atoms, for straight-chain or branched alkynyl having 2 to 6 carbon atoms , for straight-chain or branched alkoxy with 1 to 6 carbon atoms or for in each case optionally monosubstituted to trisubstituted, identically or differently substituted, phenylalkyl, phenyl or phenoxy with optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part, the following being suitable as phenyl substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and optionally single to triple, identical or different, phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms,

A represents a double-linked alkanediyl radical having 1 to 6 carbon atoms and

X ^{1 represents} oxygen or sulfur, where R ^{4 represents} hydrogen, fluorine, chlorine, bromine, cyano, nitro or straight-chain or branched, optionally monosubstituted alkyl having 1 to 6 carbon atoms, the following being suitable as substituents:

Hydroxy, cyano, amino, each straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N-dialkylamino, each with 1 to 6 carbon atoms in the individual alkyl parts;

R ⁴ also 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 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine, for each straight-chain or branched haloalkenyl or haloalkynyl each having 2 to 4 carbon atoms and 1 to 7 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine or for each straight-chain or branched alkoxy, alkylthio, alkylsulfonyl, alkylsulfonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the individual Represents alkyl, furthermore represents cycloalkyl having 3 to 7 carbon atoms which is optionally monosubstituted to pentasubstituted identically or differently by chlorine, bromine, methyl and / or ethyl, and additionally represents phenyl or phenoxy which is monosubstituted to trisubstituted by identical or different compounds where the following are possible as phenyl substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and optionally mono- to triple, identical or different, phenyl or R ^ substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, represents a radical of the formula

R ^{5 represents} hydrogen, cyano, amino, aminocarbonyl or straight-chain or branched, optionally mono- or polysubstituted, identically or differently substituted alkyl having 1 to 6 carbon atoms, the following being suitable as substituents: fluorine, chlorine, bromine, hydroxy, cyano, amino , each straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N-dialkylamino, each having 1 to 4 carbon atoms in the individual alkyl parts;

R ⁵ also for each straight-chain or branched alkenyl or alkynyl each having 2 to 6 carbon atoms, for each straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N, N-dialkylamino or

Alkylidenimino, each having 1 to 6 carbon atoms in the individual alkyl parts, is also optionally substituted by up to five times, identical or different, by chlorine, bromine, methyl and / or ethyl tes cycloalkyl having 3 to 7 carbon atoms, moreover in each case optionally phenyl or phenoxy which is monosubstituted to trisubstituted by identical or different substituents, the following being suitable as phenyl substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and optionally one to three times, the same or different

Halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms substituted phenyl,

R ⁶ for each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms or for a radical of the formula

stands,

R ^{7 represents} straight-chain or branched alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 7 carbon atoms,

R ⁸ and R ⁹ are each independently of one another in each case for hydrogen, for straight-chain or branched alkyl having 1 to 6 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each having 2 to 6 carbon atoms, for cycloalkyl with 3 to 7 carbon atoms or for each optionally simple up to triple, identical or differently substituted phenylalkyl or phenyl with optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part, where the following are in each case possible as phenyl substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl, each with 1 to 4 carbon atoms in the individual alkyl parts, and optionally one to three times, identical or different, by halogen and / or straight-chain or branched alkyl with 1 phenyl substituted up to 4 carbon atoms; or R ⁸ and R ⁹ together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which may be 1 to 4 times, identically or differently, substituted by straight-chain or branched alkyl having 1 to 3 carbon atoms and which may be 1 can contain further heteroatoms - in particular nitrogen, oxygen or sulfur - and R ^{1 1} either independently of one another in each case for straight-chain or branched alkyl having 1 to 6 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each having 2 to 6 carbon atoms, for straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine - for each straight-chain or branched haloalkenyl or haloalkynyl each with 2 to 4 carbon atoms and 1 to 7 identical or different halogen atoms - in particular other fluorine,

Chlorine, and / or bromine, for straight-chain or branched alkoxyalkyl or alkoxy each having 1 to 6 carbon atoms in the individual alkyl parts, for cycloalkyl with 3 to 7 carbon atoms, for cycloalkylalkyl with 3 to 7 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the straight-chain or branched alkyl part, for phenyl or phenylalkyl which is optionally monosubstituted to trisubstituted in the same or different manner and optionally having 1 to 4 carbon atoms in the straight-chain or branched alkyl part or for heteroaryl having 2 to 9 carbon atoms and monosubstituted or trisubstituted in the same or different ways and 1 to 3 identical or different heteroatoms, in particular nitrogen, oxygen and / or sulfur, where as aryl or. Heteroaryl substituents are possible: Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and optionally mono- to triple, identical or different, substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms; or R ¹⁰ and R ¹¹ together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally monosubstituted to tetrasubstantially, identically or differently, by straight-chain or branched alkyl having 1 to 3 carbon atoms, which optionally 1 can contain further heteroatoms - in particular nitrogen, oxygen or sulfur - and

X ^{2 represents} oxygen or sulfur.

Compounds of the formula (I) in which

Het stands for a heterocycle of the formula or

R ¹ , R ² and R ³ independently of one another each represent fluorine, chlorine, bromine, for straight-chain or branched alkyl having 1 to 4 carbon atoms, for straight-chain or branched alkenyl having 2 to 4 carbon atoms, for straight-chain or branched alkynyl having 2 to 4 carbon atoms , for straight-chain or branched alkoxy with 1 to 4 carbon atoms or for phenylalkyl, phenyl or phenoxy which are optionally mono- or disubstituted, identically or differently, and optionally with 1 to 3 carbon atoms in the straight-chain or branched alkyl part, the following being suitable as phenyl substituents:

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s - or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally one to two times, identical or different, by fluorine, chlorine / or ethyl substituted phenyl; A represents a double-linked alkanediyl radical having 1 to 4 carbon atoms and

X ^{1 represents} oxygen or sulfur, where

R ^{4 represents} hydrogen, fluorine, chlorine, bromine, cyano, nitro or straight-chain or branched, optionally monosubstituted alkyl having 1 to 4 carbon atoms, the following being suitable as substituents:

Hydroxy, cyano, amino, each straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N-dialkylamino, each with 1 to 4 carbon atoms in the individual alkyl parts;

R ⁴ also for each straight-chain or branched alkenyl or alkynyl each having 2 to 4 carbon atoms, for haloalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine, for each straight-chain or branched haloalkenyl or Haloalkynyl each with 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine - or for straight-chain or branched alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl or alkoxycarbonyl each with 1 to 4 carbon atoms in the individual alkyl parts stands, also stands for cycloalkyl with 3 to 6 carbon atoms, also for each optionally single or double, identical or different substituted phenyl or phenoxy, where the following are suitable as phenyl substituents:

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally one to two, chlorine, identical or different, fluorine, identical or different, fluorine Methyl and / or ethyl substituted phenyl; or R ^ represents a radical of the formula

R ^{5 represents} hydrogen, cyano, amino, aminocarbonyl or straight-chain or branched, optionally mono- or polysubstituted, identically or differently substituted alkyl having 1 to 4 carbon atoms, the following being suitable as substituents: fluorine, chlorine, bromine, hydroxy, cyano, amino , in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N-dialkylamino, each having 1 to 3 carbon atoms in the individual alkyl parts;

R ⁵ also for each straight-chain or branched alkenyl or alkynyl each having 2 to 4 carbon atoms, for each straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N, N-dialkylamino or

Alkylidenimino each having 1 to 4 carbon atoms in the individual alkyl parts, also stands for cycloalkyl with 3 to 6 carbon atoms, and also stands for phenyl or phenoxy which is monosubstituted or disubstituted in the same way or differently, the following being suitable in each case as phenyl substituents: Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally one to two, chlorine, identical or different, fluorine, identical or different, fluorine Methyl and / or ethyl substituted phenyl;

R ⁶ for each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms or for a radical of the formula

stands,

R ^{7 represents} straight-chain or branched alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms,

R ⁸ and R ⁹ are each independently of one another in each case for hydrogen, for straight-chain or branched alkyl having 1 to 4 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each with 2 to 4 carbon atoms, for cycloalkyl with 3 to 6 carbon atoms or for each optionally simple or phenylalkyl or phenyl which are substituted twice, identically or differently and optionally have 1 to 3 carbon atoms in the straight-chain or branched alkyl part, where the following are in each case possible as phenyl substituents:

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally one to two, chlorine, identical or different, fluorine, identical or different, fluorine Methyl and / or ethyl substituted phenyl; or R ⁸ and R ⁹ together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally mono- or disubstituted, identically or differently, by methyl and / or ethyl and which optionally contains 1 further heteroatom - in particular Nitrogen, oxygen or sulfur - can contain, and R ¹¹ either independently of one another in each case for straight-chain or branched alkyl having 1 to 4 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each having 2 to 4 carbon atoms, for straight-chain or branched haloalkyl having 1 to 4 carbon atoms 3 carbon atoms and 1 to 7 identical or different halogen atoms - especially fluorine, chlorine and / or bromine - for each straight-chain or branched haloalkenyl or haloalkynyl each with 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms - especially fluorine, chlorine, and / or bromine -, for each straight or branched

Alkoxyalkyl or alkoxy, each with 1 to 4 carbon atoms in the individual alkyl parts, for cycloalkyl with 3 to 6 carbon atoms, for cycloalkylalkyl with 3 to 6 carbon atoms in the cycloalkyl part and 1 or 2 carbon atoms in the alkyl part, each optionally mono- or disubstituted, identically or differently substituted Phenyl or phenylalkyl with optionally 1 to 3 carbon atoms in the straight-chain or branched alkyl part or for optionally mono- or disubstituted, identically or differently substituted heteroaryl with 2 to 5 carbon atoms and 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur, where aryl or heteroaryl substituents are suitable:

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or against optionally phenyl substituted once or twice, identically or differently by fluorine, chlorine, bromine, methyl and / or ethyl; or R ¹⁰ and R ¹¹ together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally mono- or disubstituted, identically or differently, by methyl and / or ethyl and which optionally contains 1 further heteroatom - in particular Nitrogen, oxygen or sulfur - can contain and

X ^{2 represents} oxygen or sulfur. In addition to the compounds listed in the preparation examples, the following substituted triazolinones of the general formula (I) may be mentioned individually:

-26

If, for example, 1-chlorocarbony 1-3 -dimethylamino-4-methyl-1,2,4-triazolin-5-one and trimethylsilylmethylamine are used as starting materials, the course of the reaction of process (a) according to the invention can be represented by the following formula:

If, for example, 3-dimethylamino-2-methyl-1,2,4-triazolin-5-one and trimethylsilylmethyl isocyanate are used as starting materials, the course of the reaction of process (b) according to the invention can be represented by the following formula:

Formula (II) provides a general definition of the 1-chloro (thio) carbonyltriazolinones required as starting materials for carrying out process (a) according to the invention. In this formula (Et), Het and χl preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the compounds of the formula (I) according to the invention.

The 1-chloro (thio) carbonyltriazolinones of the formula (II) are known (see, for example, EP 431 390; EP 283 876; EP 298 371).

Formula (III) provides a general definition of the amines which are further required as starting materials for carrying out process (a) according to the invention. In this formula (III), R ¹ , R ² , R ³ and A preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the compounds of the formula (I) according to the invention. The amines of the formula (III) are known or can be obtained analogously to known processes (cf., for example, J. Amer. Chem. Soc, 73 3867 [1951]; Synth. Commun., 18, (16-17) 1975-1978 ).

Formula (IV) provides a general definition of the triazolinones which are unsubstituted in the 1-position to carry out process (b) according to the invention. In this formula (IV), Het preferably represents those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.

The triazolinones of the formula (IV) which are unsubstituted in the 1 position are known or can be obtained by analogy with known processes (cf. e.g. EP 283 876; EP 431 390; EP 298 371).

Formula (V) provides a general definition of the iso (thio) cyanates required to carry out process (b) according to the invention. In this formula (V), R ¹ , R ² , R ³ , A and X ¹ preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.

The iso (thio) cyanates of the formula (V) are known or can be obtained analogously to known processes (cf., for example, Zh. Obshch. Khim. 38, 1179-1185 [1968]; Zh. Obshch. Khim. 37, 1383-1385 [1967]; J. Org. Chem. 49, 2688-2691 [1984]). Inert organic solvents are suitable as diluents for carrying out process (a) 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 or 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 triamide; Esters such as methyl acetate or ethyl acetate or bases such as pyridine. Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide or also ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, and also ammonium acetate or ammonium acetate Trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecen (DBU).

It is also possible to use the amine of the formula (III) used as reactant in a corresponding excess at the same time as a reaction auxiliary.

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 + 80 ° C.

To carry out process (a) according to the invention, generally 1.0 to 5.0 mol, preferably 1.0 to 2 mol, of amine of the formula (III) and, if appropriate, are used per mol of 1-chloro (thio) carbonyltriazolinone of the formula (II) 1.0 to 5.0 mol, preferably 1.0 to 2 mol, of base as reaction auxiliary. The reaction is carried out, worked up and isolated by known processes (see, for example, EP 283 876 or the preparation examples). Inert organic solvents are suitable as diluents for carrying out process (b) according to the invention. The solvents listed in the description of the implementation of process (a) according to the invention are preferably used.

If appropriate, process (b) according to the invention can be carried out in the presence of a suitable basic reaction auxiliary. As such, everyone comes usual inorganic or organic bases in question. Tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU) are preferably used.

However, the addition of basic reaction aids is not absolutely necessary.

The reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between 0 ° C and + 150 ° C, preferably at temperatures between + 40 ° C and + 120 ° C.

Process (b) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.

To carry out process (b) according to the invention, generally 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, of iso (thio) cyanate of the formula are employed per mole of unsubstituted triazolinone of the formula (TV) in the 1-position (V) and optionally 0.01 to 5.0 mol, preferably 0J to 2.5 mol, of base as reaction auxiliary.

The reaction is carried out, worked up and isolated by known processes (see, for example, EP 283 876 or the preparation examples).

The end products of the formula (I) are purified using customary methods, for example by column chromatography or by recrystallization.

The characterization is carried out using the melting point or, in the case of non-crystallizing compounds, using proton nuclear magnetic resonance spectroscopy (! H-NMR).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers become. 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:

Dicotyledonous 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, for example on industrial and rail tracks and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, for example forest, ornamental wood, fruit, wine, Zi trus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annual crops.

The active compounds according to the invention can be used with particularly good success for controlling monocotyledonous and dicotyledon weeds in monocotyledon crops such as, for example, maize.

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances.

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

If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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 or dimethyl sulfoxide, and water. Solid carrier materials are suitable: for example 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; Solid carriers for granules are suitable: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; Possible emulsifying and / or foaming 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, leaching lignin sulfite 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 ingredient, 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 dichloropicolinic acid, dicamba or picloram; Aryloxyalkanoic acids such as 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 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 chloroturon, 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, for example, amidosulfuron, bensulfüron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfüron-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 atrazine, cyanazine, simazin, simetryne, terbutryne and terbutylazine; Triazinones such as hexazinone, metamitron and metribuzin; Others, such as, for example, aminotriazole, Benfüresate, 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; Spray, sprinkle. 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. Generally lie gene the application rates between 0.01 and 10 kg of active ingredient per hectare of soil, preferably between 0.05 and 5 kg per hectare.

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

Production examples: Example 1:

(Process a) To 5.1 g (0.025 mol) of 1-chlorocarbonyl-3-dimethylamino-4-methyl-1,2,4-triazolin-5-one in 100 ml of acetonitrile, a solution of is added dropwise with stirring at room temperature 2.68 g (0.025 mol) of trimethylsilylmethylamine and 2.53 g (0.025 mol) of triethylamine in 50 ml of acetonitrile and, after the addition has ended, stirred for 60 minutes at room temperature. For working up, precipitated triethylamine hydrochloride is filtered off, the filtrate is concentrated in vacuo, the residue is taken up in 150 ml of dichloromethane, washed three times with 50 ml of water each time, dried over sodium sulfate and again concentrated in vacuo. The residue is recrystallized from cyclohexane.

4.0 g (59% of theory) of 3-dimethylamino-4-methyl-1- (trimethylsilylmethylaminocarbonyl) -1,2,4-triazolin-5-one with a melting point of 79-81 ° C. are obtained.

Example 2:

Method (b)

5.25 g (0.03 mol) of 2-methyl-3- (4-morpholinyl) - (1H) -1,2,4-triazolin-5-one in 100 ml of acetonitrile are added at room temperature with stirring 3. 87 g (0.03 mol) of trimethylsilyl isocyanate and 3 drops of l, 8-diazabicyclo- [5.4.0] -undec-7-ene (DBU), then stirred for 4 hours at room temperature, then concentrated in vacuo and the residue crystallized out Cyclohexane / ethyl acetate (1: 1).

6.5 g (69% of theory) of 2-methyl-3- (4-morpholinyl) -1- (trimethylsilylmethylaminocarbonyl) -1,2,4-triazolin-5-one with a melting point of 133-134 ° C. are obtained .

The following substituted triazolinones of the general formula (I) are obtained in a corresponding manner and in accordance with the general information on the preparation:

Examples of use:

In the following application examples, the compound listed below was used as the reference substance:

2-methyl-3-dimethylamino-1- [N- (2,2-dimethyl-1-propyl) aminocarbonyl] -1,2,4-triazolin-5-one

(known from EP 431 390)

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, one 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 annihilation

In this test, for example, the compound according to Preparation Example 3 shows a clear superiority in effectiveness as well as a considerably improved crop selectivity compared to the prior art.

Example B: Post emergence test

Solvent: 5 parts by weight of acetone

Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are 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 annihilation

In this test, for example, the compound according to Preparation Example 3 shows a clear superiority in effectiveness as well as an improved crop selectivity compared to the prior art.

Claims

1. Substituted triazolinones of the general formula (I),

in which

Het for a heterocycle of the formula or

stands,

R ¹ , R ² and R ³ each independently represent halogen, alkyl, alkenyl, alkynyl, alkoxy or optionally substituted arylalkyl, aryl or aryloxy, A represents a double-linked alkanediyl radical and

X ^{1 represents} oxygen or sulfur, where

R ⁴ for hydrogen, halogen, cyano, nitro, for optionally substituted

Alkyl, for alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxy,

R ⁵ for hydrogen, cyano, for optionally substituted alkyl, for alkenyl, alkynyl, alkoxy, alkoxycarbonyl, aminocarbonyl, for amino, N-alkylamino, N, N-dialkylamino, alkylidenimino or represents optionally substituted cycloalkyl, aryl or aryloxy,

R ^{6 represents} alkyl, alkoxy, alkylthio or a radical of the formula

R ^{7 represents} alkyl or cycloalkyl,

R ¹⁰ and R ^{1 1} either independently of one another each represent alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alkoxy, cycloalkyl, cycloalkylalkyl, each optionally substituted aryl, arylalkyl or heteroaryl or together with the nitrogen atom to which they are attached are bound, represent an optionally substituted heterocycle and

X ^{2 represents} oxygen or sulfur.

2. Substituted triazolinones of the general formula (I) according to claim 1, characterized in that

Het for a heterocycle of the formula or

stands,

R ¹ , R ² and R ³ independently of one another each for fluorine, chlorine, bromine, iodine, for straight-chain or branched alkyl having 1 to 8 carbon atoms, for straight-chain or branched alkenyl with 2 to 8 carbon atoms, for straight-chain or branched alkynyl with 2 to 8 carbon atoms, for straight-chain or branched alkoxy with 1 to 8 carbon atoms or for each arylalkyl, aryl or aryloxy which is mono- or polysubstituted, identically or differently, by each have 6 to 10 carbon atoms in the aryl part and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl part, the aryl substituents in each case being:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 6 carbon atoms in the individual alkyl parts and, if appropriate, mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms,

A represents a double-linked alkanediyl radical having 1 to 8 carbon atoms and

X ^{1 represents} oxygen or sulfur, where

Fluorine, chlorine, bromine, iodine, hydroxy, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N-dialkylamino, each with 1 to 8 carbon atoms in the individual alkyl parts;

R ⁴ also for straight-chain or branched alkenyl or

Alkynyl, each with 2 to 8 carbon atoms, for each straight-chain or branched haloalkenyl or haloalkynyl each having 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine or for straight-chain or branched alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl each having 1 to 8 Carbon atoms in the individual alkyl parts also stands for cycloalkyl with 3 to 8 carbon atoms which is optionally substituted once or more, in the same way or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, and also in each case optionally in single or multiple form, the same or differently substituted aryl or aryloxy each having 6 to 10 carbon atoms, the following being suitable as aryl substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts and, if appropriate, mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms, phenyl or R ^{4 represents} a radical of the formula

R ⁵ represents hydrogen, cyano, amino, aminocarbonyl or straight-chain or branched, optionally mono- or polysubstituted, identically or differently substituted alkyl having 1 to 8 carbon atoms, the following being suitable as substituents:

Fluorine, chlorine, bromine, iodine, hydroxy, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N- Dialkylamino each having 1 to 8 carbon atoms in the individual alkyl parts;

R ⁵ also for each straight-chain or branched alkenyl or alkynyl each having 2 to 8 carbon atoms, for each straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino,

N, N-dialkylamino or alkylideneimino each having 1 to 8 carbon atoms in the individual alkyl parts, moreover in each case optionally cycloalkyl having 3 to 8 substituted once or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms Carbon atoms also stands for aryl or aryloxy, each of which is optionally mono- or polysubstituted by identical or different substituents, each having 6 to 10 carbon atoms, the following being suitable as aryl substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl,

Alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl each having 1 to 6 carbon atoms in each Alkyl parts and optionally single or multiple, identical or different, substituted by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms, phenyl, R ⁶ for each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 8 carbon atoms or for a radical of Formula stands,

R ^{7 represents} straight-chain or branched alkyl having 1 to 8 carbon atoms or cycloalkyl having 3 to 8 carbon atoms, R ⁸ and R ⁹ are each independently of one another in each case for hydrogen, 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 8 carbon atoms, for cycloalkyl with 3 to 8 carbon atoms or for each optionally simple or arylalkyl or aryl which are substituted several times, identically or differently, each having 6 to 10 carbon atoms in the aryl part and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl part, the following being suitable as aryl substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl,

Alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl each having 1 to 6 carbon atoms in each Alkyl parts and optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl with 1 to 6 carbon atoms substituted phenyl;

or R ° and R "together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally mono- or polysubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 4 carbon atoms and which, if appropriate, 1 can contain up to 2 further heteroatoms, in particular nitrogen, oxygen or sulfur,

R ¹⁰ and R ^{1 1} either independently of one another in each case 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 8 carbon atoms, for straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 same or different halogen atoms - especially fluorine, chlorine, bromine and / or iodine - for each straight-chain or branched haloalkenyl or haloalkynyl with each having 2 to 6 carbon atoms and 1 to 1 1 identical or different halogen atoms - especially fluorine, chlorine, bromine and / or iodine - for each straight-chain or branched alkoxyalkyl or alkoxy each having 1 to 8 carbon atoms in the individual alkyl parts, for cycloalkyl having 3 up to 8 carbon atoms, for

Cycloalkylalkyl with 3 to 8 carbon atoms in the cycloalkyl part and 1 to 6 carbon atoms in the straight-chain or branched alkyl part, for each aryl or arylalkyl which is monosubstituted or polysubstituted in the same or different ways, each having 6 to 10 carbon atoms in the aryl part and optionally 1 to 6 carbon atoms in the straight-chain or are branched alkyl part or are heteroaryl with 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms, in particular nitrogen, oxygen and / or sulfur, which may be monosubstituted or polysubstituted by identical or different substituents, in particular nitrogen, oxygen and / or sulfur, the following being suitable as aryl and heteroaryl substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 6 carbon atoms in the individual alkyl parts and optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms;

or R ¹⁰ and R ^{1 1} together with the nitrogen atom to which they are attached, for a saturated five- to seven-membered group which may be mono- or polysubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 4 carbon atoms

Heterocycle, which may optionally contain 1 to 2 further heteroatoms, in particular nitrogen, oxygen and / or sulfur, and X ^{2 represents} oxygen or sulfur.

3. Substituted triazolinones of the general formula (I) according to claim 1, characterized in that

Het for a heterocycle of the formula or

stands,

R ¹ , R ² and R ³ independently of one another each represent fluorine, chlorine, bromine, for straight-chain or branched alkyl having 1 to 6 carbon atoms, for straight-chain or branched alkenyl having 2 to 6 carbon atoms, for straight-chain or branched alkynyl having 2 to 6 carbon atoms stand for straight-chain or branched alkoxy with 1 to 6 carbon atoms or for phenylalkyl, phenyl or phenoxy with optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part which are optionally monosubstituted to trisubstituted in the same or different ways, where the following are suitable as phenyl substituents: halogen, Cyano, nitro, each straight-chain or branched alkyl,

Alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl or alkoximinoalkyl each having 1 to 4 carbon atoms in each Alkyl parts and optionally monosubstituted to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, A represents a doubly linked alkanediyl radical having 1 to 6 carbon atoms and X ^{1 represents} oxygen or sulfur, where

R ^{4 represents} hydrogen, fluorine, chlorine, bromine, cyano, nitro or straight-chain or branched, optionally monosubstituted alkyl having 1 to 6 carbon atoms, the following being suitable as substituents:

Hydroxy, cyano, amino, in each case straight-chain or branched alkoxy,

Alkylthio, N-alkylamino or N, N-dialkylamino each having 1 to 6 carbon atoms in the individual alkyl parts;

R ⁴ also 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 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine, for each straight-chain or branched haloalkenyl or haloalkynyl each having 2 to 4 carbon atoms and 1 to 7 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine - or for straight-chain or branched alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the individual alkyl parts, furthermore represents cycloalkyl having 3 to 7 carbon atoms which is optionally monosubstituted to pentasubstituted identically or differently by chlorine, bromine, methyl and / or ethyl, and additionally represents phenyl or P which is monosubstituted to trisubstituted identically or differently in each case henoxy stands, with the following being possible as phenyl substituents:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each with 1 to 4 carbon atoms in the individual alkyl parts and optionally single to triple, identical or different by halogen and / or straight chain saturated or branched alkyl with 1 to 4 carbon atoms substituted phenyl or R ^{4 represents} a radical of the formula

R ^{5 represents} hydrogen, cyano, amino, aminocarbonyl or straight-chain or branched, optionally mono- or polysubstituted, identically or differently substituted alkyl having 1 to 6 carbon atoms, the following being suitable as substituents:

Fluorine, chlorine, bromine, hydroxy, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N-dialkylamino, each having 1 to 4 carbon atoms in the individual alkyl parts;

R ⁵ also represents straight-chain or branched alkenyl or alkynyl each having 2 to 6 carbon atoms, each straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N, N-dialkylamino or alkylideneimino each having 1 to 6 carbon atoms in the individual alkyl parts, furthermore stands for cycloalkyl having 3 to 7 carbon atoms which is optionally monosubstituted to pentasubstituted identically or differently by chlorine, bromine, methyl and / or ethyl, and additionally stands for phenyl or phenoxy which is monosubstituted or trisubstituted identically or differently in each case, with phenyl substituents in each case:

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and optionally single to triple, identical or different, phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, R ⁶ for straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms or for a radical of the For¬

R

mel— N stands,

V

Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and optionally mono- to triple, identical or different, substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms;

or R ⁸ and R ⁹ together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which may be 1 to 4 times, identically or differently, substituted by straight-chain or branched alkyl having 1 to 3 carbon atoms and which may be 1 may contain further heteroatoms, in particular nitrogen, oxygen or sulfur, R ¹⁰ and R ^{1 1} either independently of one another each for straight-chain or branched alkyl having 1 to 6 carbon atoms, for each straight-chain or branched AL: enyl or alkynyl each having 2 to 6 carbon 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, chlorine and / or bromine - for each straight-chain or branched haloalkenyl or haloalkynyl each with 2 to 4 carbon atoms and 1 to 7 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine - , for each straight-chain or branched alkoxyalkyl or alkoxy, each with 1 to

6 carbon atoms in the individual alkyl parts, for cycloalkyl with 3 to 7 carbon atoms, for cycloalkylalkyl with 3 to 7 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the straight-chain or branched alkyl part, for each optionally mono- to trisubstituted, identically or differently substituted, phenyl or phenylalkyl optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part or for optionally mono- to trisubstituted, identically or differently substituted heteroaryl having 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur, respectively.

Heteroaryl substituents are possible:

or R ¹⁰ and R ^{1 1} together with the nitrogen atom to which they are attached, for one optionally up to four times, equal to or are different, substituted by straight-chain or branched alkyl having 1 to 3 carbon atoms, saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom - in particular nitrogen, oxygen or sulfur - and

X ^{2 represents} oxygen or sulfur.

4. Substituted triazolinones of the general formula (I) according to claim 1, characterized in that

Het for a heterocycle of the formula or

R ¹ , R ² and R ³ independently of one another each represent fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkenyl having 2 to 4 carbon atoms, straight-chain or branched alkynyl having 2 to 4 carbon atoms 4 carbon atoms, for straight-chain or branched alkoxy with 1 to 4 carbon atoms or for phenylalkyl, phenyl or phenoxy with optionally 1 or 3 carbon atoms in the straight-chain or branched alkyl part which are optionally mono- or disubstituted, identically or differently, in each case in the straight-chain or branched alkyl part, the following being suitable as phenyl substituents:

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally one to two, chlorine, identical or different, fluorine, identical or different, fluorine Methyl and / or ethyl substituted phenyl; A represents a double-linked alkanediyl radical having 1 to 4 carbon atoms and

X ^{1 represents} oxygen or sulfur, where

R ⁴ for hydrogen, fluorine, chlorine, bromine, cyano, nitro or for straight-chain or branched, optionally monosubstituted alkyl having 1 to 4

Carbon atoms stands, whereby the following can be used as substituents:

R ⁴ also for straight-chain or branched alkenyl or

Alkynyl each having 2 to 4 carbon atoms, for haloalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine, for each straight-chain or branched haloalkenyl or haloalkynyl each having 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine - or for straight-chain or branched alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl, each with 1 to 4 carbon atoms in the individual alkyl parts, and also for cycloalkyl with 3 to 6 carbon atoms stands for phenyl or phenoxy which is optionally mono- or disubstituted in the same way or differently, phenyl substituents in each case being suitable: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, met hylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, bromine, methyl and / or phenyl; or R ^{4 represents} a radical of the formula

R ^{5 represents} hydrogen, cyano, amino, aminocarbonyl or straight-chain or branched, optionally mono- or polysubstituted, identically or differently substituted alkyl having 1 to 4 carbon atoms, the following being suitable as substituents:

Fluorine, chlorine, bromine, hydroxy, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N-dialkylamino, each having 1 to 3 carbon atoms in the individual alkyl parts;

R ~ also stands for straight-chain or branched alkenyl or alkynyl each having 2 to 4 carbon atoms, for each straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N, N-dialkylamino or alkylideneimino each having 1 to 4 carbon atoms in the individual alkyl parts, also stands for cycloalkyl having 3 to 6 carbon atoms, also for phenyl or monosubstituted or disubstituted in the same or different ways

Phenoxy is available, the following being possible as phenyl substituents:

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally one to two, chlorine, identical or different, fluorine, identical or different, fluorine Methyl and / or ethyl substituted phenyl; R ⁶ represents straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms or a radical of the formula

R ⁸ and R ⁹ either independently of one another each for hydrogen, for straight-chain or branched alkyl having 1 to 4 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each

2 to 4 carbon atoms, for cycloalkyl with 3 to 6 carbon atoms or for phenylalkyl or phenyl with 1 to 3 carbon atoms optionally substituted once or twice, identically or differently, in the straight-chain or branched alkyl part, the following being suitable as phenyl substituents:

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally one to two, chlorine, identical or different, fluorine, identical or different, fluorine Methyl and / or ethyl substituted phenyl;

or R ⁸ and R ⁹ together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally mono- or disubstituted, identically or differently, by methyl and / or ethyl and which optionally contains 1 further heteroatom - in particular Nitrogen, oxygen or sulfur - can contain, R ¹⁰ and R ^{1 1} either independently of one another in each case for straight-chain or branched alkyl having 1 to 4 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each having 2 to 4 carbon atoms, for straight-chain or branched haloalkyl with 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms - especially fluorine, chlorine and / or bromine - for each straight-chain or branched haloalkenyl or haloalkynyl each with 2 to 3 carbon atoms and 1 to 5 identical or different halo genomic - especially fluorine, chlorine, and / or bromine - for straight-chain or branched alkoxyalkyl or alkoxy each having 1 to 4 carbon atoms in the individual alkyl parts, for cycloalkyl with 3 to 6 carbon atoms, for cycloalkylalkyl with 3 to 6 coblene atoms in the cycloalkyl part and 1 or 2 carbon atoms in the alkyl part, for phenyl or phenylalkyl which is optionally mono- or disubstituted in the same way or differently and optionally having 1 to 3 carbon atoms in the straight-chain or branched alkyl part or for heteroaryl with 2 to 5 carbon atoms which are monosubstituted or disubstituted in the same or different manner and There are 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur, the following being suitable as aryl or heteroaryl substituents:

Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally one to two, chlorine, identical or different, fluorine, identical or different, fluorine Methyl and / or ethyl substituted

Phenyl; or R ¹⁰ and R ^{1 1} together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally mono- or disubstituted, identically or differently, by methyl and / or ethyl and which optionally contains 1 further hetero atom - in particular nitrogen, oxygen or sulfur - can contain and

X ^{2 represents} oxygen or sulfur.

5. Process for the preparation of substituted triazolinones of the general formula (I),

in which

Het for a heterocycle of the formula or

R ¹ , R ² and R ³ are each independently halogen, alkyl, alkenyl,

Are alkynyl, alkoxy or optionally substituted arylalkyl, aryl or aryloxy,

A represents a doubly linked alkanediyl radical and

X ^{1 represents} oxygen or sulfur, where R ^{4 represents} hydrogen, halogen, cyano, nitro, optionally substituted

Alkyl, represents alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfonyl, alkoxycarbonyl, represents in each case optionally substituted cycloalkyl, aryl or aryloxy or a radical of the formula,

R ⁵ for hydrogen, cyano, for optionally substituted alkyl, for

Alkenyl, alkynyl, alkoxy, alkoxycarbonyl, aminocarbonyl, represents amino, N-alkylamino, N, N-dialkylamino, alkylidenimino or represents in each case optionally substituted cycloalkyl, aryl or aryloxy, R ⁶ for alkyl, alkoxy, alkylthio or for a radical of the formula

stands,

R ^{7 represents} alkyl or cycloalkyl,

Alkoxy, cycloalkyl, cycloalkylalkyl, each represent optionally substituted aryl, arylalkyl or heteroaryl or together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle and X ^{2 represents} oxygen or sulfur, characterized in that

a) 1-chloro (thio) carbonyltriazolinones of the formula (II),

in which

Het and X ^{1 have} the meanings given above, with amines of the formula (III),

in which

R ¹ , R ² , R ³ and A have the meanings given above, if appropriate in the presence of a diluent and, if appropriate, in Gregenwart a reaction auxiliary, or if b) triazolinones of the formula (IV) which are unsubstituted in the 1-position,

Het-H (IV) in which Het has the meaning given above, with iso (thio) cyanates of the formula (V),

in which

R ¹ , R ² , R ³ , A and X ^{1 have} the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.

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

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

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

9. 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.