DE4234306A1 - Substituted triazolinones - Google Patents

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>, R<2>, R<3>, A, X<1>, R<4>, R<5>, R<6>, R<7> and X<2> have the meanings given in the description, several processes for their production and their use as herbicides.

Description

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

It is known that certain substituted triazolinones such as Ver bond 2-methyl-3-dimethylamino-1- [N- (2,2-dimethyl-1-propyl) aminocarbonyl] - 1,2,4-triazolin-5-one have herbicidal properties (see, for example, EP 431 390).

The herbicidal activity of these previously known compounds against problems herbs, however, is just as tolerable to important crops zen not completely satisfactory in all areas of application.

New substituted triazolinones of the general formula (I)

in which
Het for a heterocycle of the formula

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
X ^{1 represents} oxygen or sulfur, where
R ⁴ for hydrogen, halogen, cyano, nitro, for optionally substituted alkyl, for alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, for in each case optionally substituted cycloalkyl, aryl or aryloxy or for a radical of the formula

stands,
R ^{5 represents} hydrogen, cyano, optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, aminocarbonyl, amino, N-alkylamino, N, N-dialkylamino, alkylidenimino or 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 ¹¹ either independently of one another each represent alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alk oxy, cycloalkyl, cycloalkylalkyl, each optionally substituted aryl, arylalkyl or heteroaryl or together with the nitrogen atom which they are bound represent an optionally substituted heterocycle and
X ^{2 represents} oxygen or sulfur,
found.

The compounds of formula (I) may optionally, depending on the type of the substituents as geometric and / or optical isomers or isomer mixtures different composition. Both the pure isomers as the isomer mixtures are also claimed according to the invention.

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

in which
Het for a heterocycle of the formula

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
X ^{1 represents} oxygen or sulfur, where
R ⁴ for hydrogen, halogen, cyano, nitro, for optionally substituted alkyl, for alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, for in each case optionally substituted cycloalkyl, aryl or aryloxy or for a radical of the formula

stands,
R ^{5 represents} hydrogen, cyano, optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, aminocarbonyl, amino, N-alkylamino, N, N-dialkylamino, alkylidenimino or 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 ¹¹ either independently of one another each represent alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alk oxy, cycloalkyl, cycloalkylalkyl, each optionally substituted aryl, arylalkyl or heteroaryl or together with the nitrogen atom which they are bound represent an optionally substituted heterocycle and
X ^{2 represents} oxygen or sulfur,
get when one

• 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 the presence of a reaction auxiliary,
  or if you
• b) in the 1-position unsubstituted triazolinones of the formula (IV), 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,

optionally in the presence of a diluent and optionally in counter were implemented a reaction aid.

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

Surprisingly, the substituted triazolinones according to the invention show the general formula (I) a significantly better herbicidal activity compared to Pro flower herbs and at the same time significantly better tolerance to important ones Cultivated plants in comparison to the known from the prior art ten triazolinones, such as the compound 2-methyl-3-dimethylamino-1- [N- (2,2-dimethyl-1-propyl) aminocarbonyl] -1,2,4-triazolin-5-one, which chemically and are effective connections.

The substituted triazolinones according to the invention are generally defined by the formula (I). Compounds of formula (I) are preferred in which
Het for a heterocycle of the formula

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 2 to 8 carbon atoms, for straight-chain or branched alkoxy with 1 to 8 carbon atoms or for any given single or multiple, identically or differently substituted arylalkyl, aryl or aryloxy each with 6 to 10 carbon atoms in the aryl part and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl are part, the aryl substituents being in each case:
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 alkoximino alkyl 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 allcyl 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
R ^{4 represents} hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro or straight-chain or branched, optionally mono- or polysubstituted, identical or different, the 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 with 1 to 8 carbon atoms in the individual alkyl parts;
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 having 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine or represents in each case straight-chain or branched alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl each having 1 to 8 carbon atoms in the individual alkyl parts, moreover in each case optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms substituted cycloalkyl having 3 to 8 carbon atoms, moreover for aryl or aryloxy, each of which is mono- or polysubstituted, identically or differently, each having 6 to 10 carbon atoms, aryl substituents being in each case:
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 alkoxinino alkyl 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 for a residue of the formula

stands,
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 with 1 to 8 carbon atoms in the individual alkyl parts;
R ⁵ also stands for straight-chain or branched alkenyl or alkynyl each having 2 to 8 carbon atoms, for each straight-chain or branched alkoxy, alkoxycarbonyl, N-allcylamino, N, N-dialkylamino or alkylidenimino each having 1 to 8 carbon atoms in the individual alkyl parts , in addition for any given single or multiple, identical or different, the cycloalkyl having 3 to 8 carbon atoms substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, and also in each case optionally single or multiple, identical 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 alkoximino alkyl, 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,
R ⁶ for each straight-chain or branched alkyl, alkoxy or alkylthio, each with 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 either independently of one another each 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 having 3 to 8 carbon atoms or for arylalkyl or aryl, each with one or more substituents, the same or differently substituted, 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, where appropriate in each case 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 the individual alkyl parts and, where appropriate, singly or multiply, identically or differently, by phenyl and / or straight-chain or branched alkyl having 1 to 6 carbon atoms, substituted phenyl;
or together with the nitrogen atom to which they are attached, stand for a single or multiple, identical or different, substituted by straight-chain or branched alkyl having 1 to 4 carbon atoms, substituted five- to seven-membered heterocycle, which may be 1 to 2 more Heteroatoms - in particular nitrogen, oxygen and / or sulfur - can contain
R ¹⁰ and R ¹¹ 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 ge rad-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine - for each straight-chain or branched haloalkylene or haloalkynyl each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine, for straight-chain or branched alkoxyalkyl or alkoxy each having 1 to 8 carbon atoms in the individual alkyl parts, for cycloalkyl having 3 to 8 carbon atoms, for cycloalkylalkyl having 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 e aryl or arylalkyl, substituted once or more 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, or for heteroaryl with 2 to 9 carbon atoms which are mono- or polysubstituted, identically or differently, and 1 are up to 4 identical or different heteroatoms - 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, where appropriate, singly or multiply, identically or differently, by phenyl and / or straight-chain or branched alkyl having 1 to 6 carbon atoms, substituted phenyl;
or together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle optionally one or more times, identically or differently, substituted or unsubstituted or unsubstituted by straight-chain or branched alkyl having 1 to 4 carbon atoms, optionally 1 to 2 can contain further heteroatoms - in particular nitrogen, oxygen and / or sulfur - and
X ^{2 represents} oxygen or sulfur.

Compounds of the formula (I) in which
Het for a heterocycle of the formula

stands,
R ¹ , R ² and R ³ independently of one another each for fluorine, chlorine, bromine, for straight-chain or branched alkyl having 1 to 6 carbon atoms, for straight-chain or branched alkenyl with 2 to 6 carbon atoms, for straight-chain or branched alkynyl with 2 to 6 Carbon atoms, 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, in the straight-chain or branched alkyl part, the following being suitable 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 alkoximino alkyl 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,
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, alkyl thio, N-alkylamino or N, N-dialkylamino, each with 1 to 6 carbon atoms in the individual alkyl parts;
also for straight-chain or branched alkenyl or alkynyl each having 2 to 6 carbon atoms, for straight-chain or branched halo genalkyl 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, alkylsulflnyl, alkylsulfonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the individual alkyl parts also 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 represents phenyl which is optionally monosubstituted to triple, identically or differently or P 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 alkoximino alkyl each having 1 to 4 carbon atoms in the individual alkyl parts and optionally mono- to triple, identical or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms substituted phenyl
or for a residue of the formula

stands,
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 with 1 to 4 carbon atoms in the individual alkyl parts;
R ⁵ also stands for 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 alkylidene no each having 1 to 6 carbon atoms in the individual alkyl parts , in addition 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 represents phenyl or phenoxy which is monosubstituted to trisubstituted identically or differently in each case, where for each as a phenyl substituent:
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 alkoximino alkyl 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,
R ⁶ for each straight-chain or branched alkyl, alkoxy or alkylthio, each with 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 either independently of one another each 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 having 3 to 7 carbon atoms or for where appropriate, mono- to trisubstituted, identically 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 having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each because straight-chain or branched alkoxycarbonyl or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and, if appropriate, single to triple, identical or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, substituted phenyl;
or together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally monosubstituted to tetrasubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 3 carbon atoms, which optionally contains 1 further heteroatom - in particular Nitrogen, oxygen and / or sulfur - can contain
R ¹⁰ and R ¹¹ 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 ge rad-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 if necessary, just to dr Phenyl or phenylalkyl which is monosubstituted or identical or different and optionally has 1 to 4 carbon atoms in the straight-chain or branched alkyl part or, if appropriate, mono- to trisubstituted, identically or differently substituted, heteroaryl having 2 to 9 carbon atoms and 1 to 3 identical or different hetero atoms - in particular nitrogen , Oxygen and / or sulfur, the following being suitable as aryl or heteroaryl 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 having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each because straight-chain or branched alkoxycarbonyl or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and, if appropriate, single to triple, identical or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, substituted phenyl;
or together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally monosubstituted to tetrasubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 3 carbon atoms, which optionally contains 1 further heteroatom - in particular Nitrogen, oxygen and / or sulfur - can contain and
X ^{2 represents} oxygen or sulfur.

Compounds of the formula (I) in which
Het for a heterocycle of the formula

stands,
R ¹ , R ² and R ³ independently of one another each for fluorine, chlorine, bromine, for straight-chain or branched alkyl having 1 to 4 carbon atoms, for straight-chain or branched alkenyl with 2 to 4 carbon atoms, for straight-chain or branched alkynyl with 2 to 4 Carbon atoms, for straight-chain or branched alkoxy having 1 to 4 carbon atoms or for each optionally mono- or disubstituted, identically or differently substituted phenylalkyl, phenyl or phenoxy with optionally 1 to 3 carbon atoms in the straight-chain or branched alkyl part, the phenyl substituents in each case being in question come:
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, fluorofluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoxirnino methyl, methoximinoethyl, ethoximinomethyl, ethoxiininoethyl or optionally, one or two, optionally, differently or by two, Chlorine, bromine, 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 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, alkyl thio, N-alkylamino or N, N-dialkylamino, each with 1 to 4 carbon atoms in the individual alkyl parts;
also for straight-chain or branched alkenyl or alkynyl each having 2 to 4 carbon atoms, for straight-chain or branched halo genalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine, for each rad-chain or branched haloalkenyl or haloainyl 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 alkoxy carbonyl each having 1 to 4 Carbon atoms in the individual alkyl parts, furthermore 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 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, trffluoromethoxy, Dffluor methoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximino methyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally or differently by one to two, optionally Chlorine, bromine, methyl and / or ethyl substituted phenyl;
or for a residue of the formula

stands,
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 with 1 to 3 carbon atoms in the individual alkyl parts;
R ⁵ also represents straight-chain or branched alkenyl or alkynyl each having 2 to 4 carbon atoms, each straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N, N-dialkylamino or alkylidene no each having 1 to 4 carbon atoms in the individual alkyl parts , furthermore stands for cycloalkyl with 3 to 6 carbon atoms, furthermore stands for phenyl or phenoxy which is monosubstituted or disubstituted in the same way or differently, where in each case 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, methoximino methyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally or differently by one to two, optionally Chlorine, bromine, methyl and / or ethyl substituted phenyl;
R ⁶ for each straight-chain or branched alkyl, alkoxy or alkylthio, each with 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 phenylalkyl or phenyl with optionally 1 to 34 carbon atoms in the straight-chain or branched alkyl part, which are mono- or disubstituted in the same way or differently, in each case in the straight-chain or branched alkyl part, the phenyl substituents in each case being:
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, methoximino methyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally or differently by one to two, optionally Chlorine, bromine, methyl and / or ethyl substituted phenyl;
or 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, May contain oxygen and / or sulfur,
R ¹⁰ and R ¹¹ are each 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 ge rad-chain or branched haloalkyl having 1 to 3 carbon atoms and 1 to 7 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 -, for each straight-chain 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, for each optionally simple or twice, the same or different en substituted phenyl or phenylalkyl with optionally 1 to 3 carbon atoms in the straight-chain or branched alkyl part or for optionally single or double ′ identical 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 are available, the aryl or heteroaryl substituents being in each case:
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, methoxymino methyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or, where appropriate, one or two, optionally Chlorine, bromine, methyl and / or ethyl substituted phenyl;
or 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, May contain oxygen and / or sulfur and
X ^{2 represents} oxygen or sulfur.

In particular, besides those listed in the production examples Compounds the following substituted triazoiinones of the general formula (I) called:

For example, 1-chlorocarbonyl-3-dimethylamino-4-methyl-1,2,4-tri is used azolin-5-one and trimethylsilylmethylamine as starting materials, so the Reakti Sequence of the process (a) according to the invention by the following formula represent:

For example, 3-dimethylamino-2-methyl-1,2,4-triazolin-5-one and Trimethylsilylmethyl isocyanate as starting materials, so the course of the reaction represent method (b) according to the invention by the following formula:

The 1-chloro (thio) carbonyltriazolinones required as starting materials for carrying out process (a) according to the invention are generally defined by the formula (II). In this formula (II), Het and X ¹ 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).

The amines required to carry out process (a) according to the invention as starting materials are generally defined by the formula (III). In this formula (III) R ¹ , R ² , R ³ and A preferably represent those radicals which are already related with the description of the compounds of formula (I) according to the invention as being preferred for these substituents.

The amines of the formula (III) are known or can be obtained in analogy to known ones Process (see, e.g., J. Amer. Chem. Soc., 73 3867 [1951]; Synth. Commun., 18, (16-17) 1975-1978).

The starting materials required to carry out process (b) according to the invention Formula (IV) generalizes triazolinones unsubstituted in the 1-position defined In this formula (IV), Het preferably represents those radicals which already in connection with the description of the substances of the invention Formula (I) were mentioned as preferred for these substituents.

The triazolinones of the formula (IV) which are unsubstituted in the 1-position are known or he available in analogy to 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 in analogy to be known methods (see, for example, Zh. Obshch. Khim. 38, 1179-1185 [1968]; Zh. Obshch. Khim. 37, 1383-1385 [1967]; J. Org. Chem. 49, 2688-2691 [1984]).

As a diluent for carrying out process (a) according to the invention inert organic solvents are suitable. These include in particular ali phatic, alicyclic or aromatic, optionally halogenated hydrocarbons substances such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, Petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride material; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or Ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or Me ethyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amines like N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyr rolidone 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 th reaction aid performed. As such come all the usual inorganic or organic bases. These include, for example, alkaline earth or Alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide or also ammonium hydroxide, alkali metal carbonates such as sodium carbonate, potassium car bonat, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbon nat, alkali or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate or ammonium acetate, and also tertiary amines, such as trimethylamine, triethylamine, Tributylamine, N, N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dime thylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or Di azabicycloundecen (DBU).

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

The reaction temperatures can be carried out when carrying out the process according to the invention Process (a) can be varied over a wide range. Generally works one at 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, 1-chloro (Thio) carbonyltriazolinone of formula (II) in general 1.0 to 5.0 mol, preferably example, 1.0 to 2 mol of amine of the formula (III) and optionally 1.0 to 5.0 mol, preferably 1.0 to 2 mol of base as a reaction auxiliary. The reaction The reaction products are carried out, worked up and isolated known methods (see, for example, EP 283 876 or the manufacturing examples).

As a diluent for carrying out process (b) according to the invention inert organic solvents are suitable. It is preferred to use the in the description of the implementation of the method (a) according to the invention counted solvents.

If appropriate, process (b) according to the invention can be used in the presence of a Neten basic reaction auxiliary can be carried out. As such, everyone comes  usual inorganic or organic bases in question. Preferably used tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethyl aniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyc looctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

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

The reaction temperatures can be carried out when carrying out the process according to the invention Process (b) can be varied over a wide range. Generally works one at 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 leads. However, it is also possible to work under increased or reduced pressure ten.

To carry out process (b) according to the invention, 1 to 1 Position of unsubstituted triazolinone of the formula (IV) in general 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol of iso (thio) cyanate of the formula (V) and optionally 0.01 up to 5.0 mol, preferably 0.1 to 2.5 mol, of base as reaction auxiliary.

He carried out the reaction, working up and isolating the reaction products follows according to known methods (see, for example, EP 283 876 or Manufacturing examples).

The end products of the formula (I) are purified using customary processes, 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 ( ¹ H-NMR).

The active compounds according to the invention can be used as defoliants, desiccants, herb kills and especially as a weed killer Weeds in the broadest sense are all plants that grow in places, where they are undesirable. Whether the substances according to the invention as total or selective Herbicides act essentially depends on the amount applied.  

The active compounds according to the invention can, for. B. used in the following plants become:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xan thium, convolvulus, ipomoea, polygonum, sesbania, ambrosia, cirsium, carduus, Sonchus, Solanum, Rorippa, RotaIa, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pi sum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, cucumis, cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorg hum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means limited to these Genres limited, but extends in the same way to other plants Zen.

The compounds are suitable for totaling depending on the concentration herb control z. B. on industrial and track systems and on paths and squares and without tree cover. Likewise, weed control compounds in permanent crops, e.g. B. forest, ornamental wood, fruit, wine, citrus, nut, banana, Coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants and for selective weed control can be used in annual crops.

The active compounds according to the invention can be particularly successful Control of monocotyledonous and dicotyledon weeds in monocotyledon crops as in for example, use corn.  

The active ingredients can be converted into the usual formulations, such as Lö solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, Active ingredient-impregnated natural and synthetic substances, fine encapsulation in po lymeric fabrics.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients are under pressure with extenders, i.e. liquid solvents the liquefied gases and / or solid carriers, if necessary with use of surface-active agents, i.e. emulsifiers and / or dispersants agents and / or foaming agents.

In the case of the use of water as an extender, z. B. also organic Lö be used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobes zoles, chlorethylenes, or methylene chloride, aliphatic hydrocarbons, such as Cyc lohexane or paraffins, e.g. B. 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 solvents such as dimethylformamide or dimethyl sulfoxide, and water.

The following are suitable as solid carriers: B. ammonium salts and natural Ge stone powders such as kaolins, clays, talc, chalk, quartz, attapulgite, Montmoril lonite or diatomaceous earth and synthetic rock powder, such as highly disperse pebbles acid, alumina and silicates; come in as solid carriers for granules question: B. broken and fractionated natural rocks such as calcite, marble, Pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules made from organic material such as sawdust, coconut bowls, corn cobs and tobacco stalks; as emulsifier and / or foam generator Funds are possible: B. non-ionic and anionic emulsifiers, such as poly oxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polygly colethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; when Dispersants are possible: B. Ligninsulfitablaugen and methyl cellulose.  

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

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan 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 Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are possible.

Known herbicides are suitable for the mixtures, for example anilides, such as e.g. B. Diflufenican and Propanil; Arylcarboxylic acids, such as. B. dichloropicolinic acid, Di camba or picloram; Aryloxyalkanoic acids, such as. B. 2,4-D, 2,4-DB, 2,4-DP, fluroxy pyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as. B. Dido fop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop- ethyl; Azinones, such as B. Chloridazon and Norffurazon; Carbamates, e.g. B. chlorine propham, Desmedipham, Phenmedipham and Propham; Chloroacetanilides such as e.g. B. Alachlor, Acetochlor, Butachlor, Metazachlor, Metolachlor, Pretilachlor and Propa chlorine; Dinitroanilines such as e.g. B. Oryzalin, Pendimethalin and Trifluralin; Diphenyl ether, such as B. Acifluorfen, Bifenox, Fluoroglycofen, Fomesafen, Halosafen, Lactofen and Oxyfluorfen; Ureas, such as B. chlorotoluron, diuron, fluometuron, isoproturon, Linuron and methabenzthiazuron; Hydroxylamines, such as. B. alloxydim, clethodim, Cycloxydim, sethoxydim and tralkoxydim; Imidazolinones, e.g. B. Imazethapyr, Imazamethabenz, imazapyr and imazaquin; Nitriles such as B. bromoxynil, dichlohenil and ioxynil, oxyacetamides such as e.g. B. Mefenacet, sulfonylureas, such as. B. Amido sulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron,  Metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulf uron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as e.g. B. butylates, Cycloate, Diallate, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiohencarb and Triallates; Triazines, e.g. B. Atrazin, Cyanazin, Simazin, Simetryne, Terbutryne and Terbutylazin; Triazinones such as e.g. B. hexazinone, metamitron and metribuzin; Other, such as B. aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, Difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.

Also a mixture with other known active ingredients, such as fungicides, insecticides den, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use solder solutions, suspensions, emulsions, powders, pastes and granules. The application is done in the usual way, e.g. B. by pouring, spraying; Spraying, Scatter.

The active compounds according to the invention can be used both before and after emergence of the plants are applied.

They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. they depends essentially on the type of effect desired. Generally lie 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 manufacture and use of the active compounds according to the invention are based on following examples.

Manufacturing examples Example 1 (Method 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 is added dropwise with stirring at room temperature Solution of 2.68 g (0.025 mol) of trimethylsilylmethylamine and 2.53 g (0.025 mol) of tri ethylamine in 50 ml of acetonitrile and, after the addition has ended, the mixture is stirred for 60 minutes Room temperature. Precipitated triethylamine hydrochloride is worked up filtered, the filtrate concentrated in vacuo, the residue in 150 ml dichloromethane added, washed three times with 50 ml of water, ge over sodium sulfate dries and concentrated again in vacuo. The residue is made from cyclohexane recrystallized.

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

Example 2 (Method b)

To 5.25 g (0.03 mol) of 2-methyl-3- (4-morpholinyl) - (1H) -1,2,4-triazolin-5-one in 100 ml Acetonitrile is added at room temperature with stirring, 3.87 g (0.03 mol) of trimethylsi- Iyl isocyanate and 3 drops of 1,8-diazabicyclo- [5.4.0] -undec-7-ene (DBU), stir then 4 hours at room temperature, then concentrated in vacuo and crystallized the residue from cyclohexane / ethyl acetate (1: 1).

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

In a corresponding manner and in accordance with the general information on the manufacture the following substituted triazolinones of the general formula (I):

Examples of use

In the following application examples, the following was listed Compound used as 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

A Ge is mixed to produce a suitable preparation of active compound most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

Seeds of the test plants are sown in normal soil and after 24 hours doused with the active ingredient preparation. You keep the amount of water per area Chen unit expediently constant. The active ingredient concentration in the preparation tion plays no role, only the application rate of the active ingredient per is decisive Area unit. 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.

A clear superiority in effectiveness as well as a significant improvement In this test, useful crop selectivity compared to the prior art is shown e.g. B. the connection according to preparation example 3.  

Example B: Post emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

A Ge is mixed to produce a suitable preparation of active compound most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5 to 15 cm so that the desired amounts of active ingredient per unit area be applied. After three weeks, the degree of damage to the plants rated in% damage compared to the development of the untreated Control.

It means:
0% = no effect (like untreated control)
100% = total annihilation.

A clear superiority in effectiveness as well as an improved utility Plant selectivity compared to the prior art shows in this test, for. B. the Compound according to production example 3.

Claims (9)

1. Substituted triazolinones of the general formula (I), in which
Het for a heterocycle of the formula 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
X ^{1 represents} oxygen or sulfur, where
R ⁴ for hydrogen, halogen, cyano, nitro, for optionally substituted alkyl, for alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, for in each case optionally substituted cycloalkyl, aryl or aryloxy or for a radical of the formula stands,
R ^{5 represents} hydrogen, cyano, optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, aminocarbonyl, amino, N-alkylamino, N, N-dialkylamino, alkylidenimino or 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 ¹¹ either independently of one another each represent alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alk oxy, cycloalkyl, cycloalkylalkyl, each optionally substituted aryl, arylalkyl or heteroaryl or together with the nitrogen atom which they 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 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 having 1 to 8 carbon atoms or for each arylalkyl, aryl or aryloxy, each having mono- or polysubstituted, identical or different, each 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 are available, 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 ge-chain or branched haloalkyl, haloalkoxy or halogen alkylthio 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 phenyl substituted once or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms,
A represents a doubly linked alkanediyl radical having 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 with 1 to 8 carbon atoms in the individual alkyl parts;
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 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, and also for each optionally with one or more, identical or different by halogen and / or straight-chain or branched alkyl 1 to 4 carbon atoms is substituted cycloalkyl with 3 to 8 carbon atoms, and also stands for aryl or aryloxy, each of which is mono- or polysubstituted in the same way or differently, each having 6 to 10 carbon atoms, aryl substituents being in each case:
Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms, each ge-chain or branched haloalkyl, haloalkoxy or halogen alkylthio 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 substituted by phenyl or by a radical of the formula stands,
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 with 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 alkylideneimino each having 1 to 8 carbon atoms in the individual alkyl parts , also represents in each case optionally singly or multiply, identically or differently substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, and also in each case optionally singly or multiply, identically 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 ge-chain or branched haloalkyl, haloalkoxy or halogen alkylthio 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 phenyl substituted once or more times, 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 in each case optionally Arylalkyl or aryl, substituted one or more times, with the same or different substitution, 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 ge-chain or branched haloalkyl, haloalkoxy, haloalkyl thio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alk oxycarbonyl 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;
or 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 optionally contains 1 to 2 further heteroatoms - can contain in particular nitrogen, oxygen and / or sulfur,
R ¹⁰ and R ¹¹ are each 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 up 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 13 identical or different halogen atoms - especially fluorine, chlorine, bromine and / or iodine, for straight-chain or branched alkoxyalkyl or alkoxy each having 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 ver branched alkyl part, for each optionally e aryl or arylalkyl, substituted once or more, 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 or, if appropriate, singly or multiply, identical or differently substituted heteroaryl having 2 to 9 carbon atoms and There are 1 to 4 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur, the aryl and heteroaryl substituents being in each case
Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms, each ge-chain or branched haloalkyl, haloalkoxy, haloalkyl thio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alk oxycarbonyl 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;
or 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 optionally contains 1 to 2 further heteroatoms - in particular nitrogen, oxygen and / or sulfur - can contain 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 stands,
R ¹ , R ² and R ³ are each independently of one another for fluorine, chlorine, bromine, for ge wheel-chain or branched alkyl having 1 to 6 carbon atoms, for ge wheel-chain or branched alkenyl with 2 to 6 carbon atoms, for straight-chain or branched alkynyl with 2 to 6 carbon atoms, for straight-chain or branched alkoxy having 1 to 6 carbon atoms or for phenylalkyl, phenyl or phenoxy which are optionally monosubstituted to trisubstituted in the same or different ways and optionally having 1 to 4 carbon atoms in the straight-chain or branched alkyl part, phenyl substituents being suitable in each case :
Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each ge-chain or branched haloalkyl, haloalkoxy or halogen alkylthio 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, 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;
also for 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, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the stands for individual alkyl parts, in addition for each optionally single to five times, identically or differently substituted by chlorine, bromine, methyl and / or ethyl cycloalkyl having 3 to 7 carbon atoms, and also in each case optionally optionally up to three times, identically or differently substituted phenyl or P 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 ge-chain or branched haloalkyl, haloalkoxy or halogen alkylthio 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, phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms or for a radical of the formula stands,
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 optionally substituted by up to five times, identically or differently, by chlorine, bromine, methyl and / or ethyl, and also stands for phenyl or phenoxy which is optionally monosubstituted to triple, identical or differently substituted, where The following are each suitable as phenyl substituents:
Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each ge-chain or branched haloalkyl, haloalkoxy or halogen alkylthio 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, phenyl substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms,
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 ge 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 phenylalkyl or phenyl which is monosubstituted to trisubstituted by the same or different substituents and optionally has 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 ge-chain or branched haloalkyl, haloalkoxy, haloalkyl thio 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 together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally monosubstituted to tetrasubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 3 carbon atoms and which optionally contains 1 further heteroatom - in particular nitrogen , Oxygen and / or sulfur - can contain
R ¹⁰ and R ¹¹ either independently of one another each 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 having 1 to 4 carbon atoms and 1 up to 9 identical or different halogen atoms - especially 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 - especially 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 having 3 to 7 carbon atoms, for cycloalkylalkyl having 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 simply up to triple, identically or differently substituted phenyl or phenylalkyl with optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part or for optionally monosubstituted to triple, identically or differently substituted heteroaryl with 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms - in particular nitrogen, Oxygen and / or sulfur are available, aryl or heteroaryl substituents being suitable:
Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each ge-chain or branched haloalkyl, haloalkoxy, haloalkyl thio 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 trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms;
or together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally monosubstituted to tetrasubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 3 carbon atoms and which optionally contains 1 further heteroatom - in particular nitrogen , Oxygen and / or sulfur - can contain 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 stands,
R ¹ , R ² and R ³ independently of one another each for fluorine, chlorine, bromine, for ge wheel-chain or branched alkyl having 1 to 4 carbon atoms, for ge wheel-chain or branched alkenyl with 2 to 4 carbon atoms, for straight-chain or branched alkynyl with 2 to 4 carbon atoms, for straight-chain or branched alkoxy with 1 to 4 carbon atoms or for each optionally mono- or disubstituted, identically or differently substituted phenylalkyl, phenyl or phenoxy with optionally 1 to 3 carbon atoms in the straight-chain or branched alkyl part, where phenyl substituents are suitable in each case :
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-But oxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally different from one to two, identical or Chlorine, bromine, 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 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;
also for straight-chain or branched alkenyl or alkynyl each having 2 to 4 carbon atoms, for straight-chain or branched 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 alkylsulflnyl, alkylsulfonyl or alkoxycarbonyl, each having 1 to 4 carbon atoms in the individual alkyl parts, is also cycloalkyl having 3 to 6 carbon atoms, and also each optionally single or double, the same or differently substituted phenyl or phenoxy, 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-But oxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally different from one to two, identical or Chlorine, bromine, methyl and / or ethyl substituted phenyl;
or for a residue of the formula stands,
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 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 , furthermore stands for cycloalkyl with 3 to 6 carbon atoms, furthermore stands for phenyl or phenoxy which is mono- or disubstituted in the same way or differently, where in each case the following are possible as phenyl substituents:
Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propy1, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-But oxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally different from one to two, identical or Chlorine, bromine, 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 ge 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 cycloalkyl with 3 to 6 carbon atoms or for in each case optionally mono- or disubstituted, identically or differently substituted phenylalkyl or phenyl with optionally 1 to 34 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-but oxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally different from one to two, the same or Chlorine, bromine, methyl and / or ethyl substituted phenyl;
or 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 and / or sulfur - can contain
R ¹⁰ and R ¹¹ are each 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 3 carbon atoms and 1 up 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-chain or branched alkoxyalkyl or alkoxy each having 1 to 4 carbon atoms in the individual alkyl parts, for cycloalkyl having 3 to 6 carbon atoms, for cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl part and 1 or 2 carbon atoms in the alkyl part, for each if necessary, single or double, identical or different ed 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 Are 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-But oxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or optionally different from one to two, identical or Chlorine, bromine, methyl and / or ethyl substituted phenyl;
or 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 and / 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 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
X _{1 represents} oxygen or sulfur, where
R ⁴ for hydrogen, halogen, cyano, nitro, for optionally substituted alkyl, for alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl, for in each case optionally substituted cycloalkyl, aryl or aryloxy or for a radical of the formula stands,
R ^{5 represents} hydrogen, cyano, optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, aminocarbonyl, amino, N-alkylamino, N, N-dialkylamino, alkylidenimino or optionally substituted cycloalkyl, aryl or aryloxy ,
R ⁶ for Alky1, 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 ¹¹ either independently of one another each represent alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, alk oxy, cycloalkyl, cycloalkylalkyl, each optionally substituted aryl, arylalkyl or heteroaryl or together with the nitrogen atom which they are bound represent an optionally substituted heterocycle and
X ^{2 represents} oxygen or sulfur,
characterized in that one

• 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 the presence of a reaction auxiliary,
  or if you
• 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 by a content of at least one Substituted triazolinone of the general formula (I) according to claim 1 until 5. 7. Process for combating undesirable plants, characterized records that substituted triazolinones of the general formula (I) according to of claims 1 to 5 can act on plants and / or their habitat. 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 the claims 1 to 5 mixed with extenders and / or surface-active substances.