DE19835943A1 - Substituted triazinones - Google Patents

Abstract

The invention relates to new substituted triazinones of the general formula (I), in which n, Q, R<1>, R<2>, R<3>, R<4> and R<5> have the meanings given in the description, to methods for producing same and to their use as herbicides.

Description

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

It is already known that certain substituted triazinones have herbicidal properties have (see. EP-A-150677, WO-A-94/03454, DE-A-33 39 859, JP-A-10053508 - zi in Chem. Abstracts 128: 227316). The herbicidal activity of this ver However, ties are not satisfactory in all respects.

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

in which
n represents the numbers 0 or 1,
Q represents O (oxygen), S (sulfur), NH or N (alkyl),
R ^{1 represents} hydrogen or halogen,
R ^{2 represents} cyano, carbamoyl or thiocarbamoyl,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, alkyl, alkenyl, Alkynyl, alkoxy, aryl, alkyl sulfonyl or arylsulfonyl,
A ¹ furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A ^{2 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, alkyl, alkoxy, Aryl, alkylsulfonyl or arylsulfonyl,
A ² furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A ^{3 represents} hydrogen with the proviso that in this case A ¹ and / or A ² do not represent a single bond if R ^{1 represents} hydrogen,
A ³ furthermore for hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, di alkylamino, which are optionally substituted by halogen or alkoxy , Alkoxycarbonyl or dialkoxy (thio) phosphoryl, for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl, each optionally substituted by halogen, each optionally substituted by halogen, cyano, carboxy, alkyl and / or alkoxy carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, or for each aryl, aryloxy, optionally substituted by nitro, cyano, carboxy, halogen, alkyl, haloalkyl, alkyloxy, haloalkyloxy and / or alkoxycarbonyl, Aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbon yl stands,
A ³ also represents in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, nOxa diazolyl, thiadiazolyl, pyridinyl or pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl
R ^{4 represents} hydrogen, cyano, hydroxy, amino, or each optionally substituted by halogen substituted alkyl, alkoxy, alkylamino, dialkylamino, alkenyl, alkynyl or cycloalkyl, and
R ^{5 stands} for hydrogen or for alkyl, alkenyl, alkynyl or cycloalkyl, which is in each case optionally substituted by cyano, halogen, alkoxy or alkoxycarbonyl, and - only if n stands for the number 0 - also cyano, carbamoyl, thiocarbamoyl or halogen .

In the event that in the general formula (I) n stands for the number 1, the invention also includes the compounds of the formula (I) tautomeric and / or isomeric compounds of the general formula (IA) - hereinafter, in which Q , R ¹ , R ² , R ³ R ⁴ and R ^{5 have} the meaning given above - with a.

In the definitions, the hydrocarbon chains, such as alkyl, are also linked with heteroatoms, such as in alkoxy - in each case straight-chain or branched.

The invention preferably relates to compounds of the formulas (I) in which
n represents the numbers 0 or 1,
Q represents O (oxygen), S (sulfur), NH or N (C ₁ -C ₄ alkyl),
R ^{1 represents} hydrogen, fluorine, chlorine or bromine,
R ^{2 represents} cyano, carbamoyl or thiocarbamoyl,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, C ₁ -C _6- alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -alkoxy, phenyl, C ₁ -C ₆ -alkylsulfonyl or phenylsulfonyl,
A ¹ further for C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkanediyl, C ₂ -C ₆ -azaalkenediyl, C ₂ -C ₆ -alkanediyl, C ₂ -C ₆ -alkanediyl, C ₃ -C for each optionally substituted by fluorine and / or chlorine _6- cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,
A ^{2 represents} a single bond, represents O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, phenyl, C ₁ -C ₆ - alkylsulphonyl or phenylsulphonyl,
A ² also for C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ -zazaalkenediyl, C ₂ -C ₆ -alkanediyl, C ₃ -C. Each substituted by fluorine and / or chlorine _6- cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,
A ^{3 represents} hydrogen with the proviso that in this case A ¹ and / or A ² do not represent a single bond if R ^{1 represents} hydrogen,
A ³ furthermore for hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for C optionally substituted by fluorine, chlorine or C ₁ -C ₆ -alkoxy ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkyl thio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylamino, di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₆ alkoxycarbonyl or di (C ₁ -C ₆ alkoxy) - (thio) phosphoryl, each optionally substituted by fluorine and / or chlorine C ₂ -C ₆ alkenyl, CC ₆ alkenyloxy, C ₂ -C ₆ alkenylamino, C ₂ -C ₆ alkylidene amino, C ₂ -C ₆ alkenyloxy car bonyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ -alkynyloxy, C ₂ -C ₆ -alkynylamino or C ₂ -C ₆ -alkynyloxy-carbonyl, for each optionally by fluorine, chlorine, cyano, carboxy, C ₁ -C ₄ -alkyl and / or C ₁ -C ₄ -alkoxy carbonyl substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyloxy, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ -al koxy, C ₃ -C ₆ -cycloalkyloxycarbonyl or C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkoxy carbonyl, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, C ₁ - C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkyl oxy, C ₁ -C ₄ haloalkyloxy and / or C ₁ -C ₄ alkoxycarbonyl substituted phenyl, phenyloxy, phenyl-C ₁ -C ₄ -alkyl, phenyl-C ₁ -C ₄ -alkoxy, phenyloxy-carbonyl or phenyl-C ₁ -C ₄ -alkoxy-carbonyl,
A ³ furthermore represents in each case optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolylidyl, pyridolylidyl, pyridolylidyl, pyridolylidyl, pyridylylidyl, pyridylylidyl, pyridolylidyl, pyridyl ,
R ^{4 is} hydrogen, cyano, hydroxy, amino, or for C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, C ₁ -C ₆ -alkylamino, di- (optionally substituted by fluorine and / or chlorine in each case C ₁ -C ₄ alkyl) amino, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or C ₃ -C ₆ cycloalkyl, and
R ^{5 is} hydrogen or is in each case optionally substituted by cyano, fluorine, chlorine, C ₁ -C ₆ -alkoxy or C ₁ -C ₆ -alkoxy-carbonyl-substituted C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ alkynyl or C ₃ -C ₆ cycloalkyl, and - only in the case where n stands for the number 0 - also cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine.

The invention preferably also relates to compounds of the formulas (IA) in which Q, R ¹ , R ² , R ³ , R ⁴ and R ^{5 have} the meanings preferably given above.

The invention relates in particular to compounds of the formula (I) in which
n represents the numbers 0 or 1,
Q represents O (oxygen), S (sulfur), NH or N (CH ₃ ),
R ^{1 represents} hydrogen, fluorine or chlorine,
R ^{2 represents} cyano, carbamoyl or thiocarbamoyl,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, represents O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, propenyl, butenyl, propynyl, butinyl, methoxy, ethoxy, n- or i-propoxy, phenyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, or phenylsulfonyl,
A ¹ furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ² for a single bond, for oxygen; Sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, where A ^{4 represents} hydrogen, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy , Methyl sulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A ² furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ³ for hydrogen, hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, n- , i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n- , i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-Propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, for each optionally fluorine or chlorine substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxy carbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino , Propynyloxycarbonyl or butynyloxycarbonyl, for each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclo-propylmethoxy, Cyclobutylmethoxy, Cyclo pentylmethoxy, Cyclohexylmethoxy, Cyclopentylidenamino, Cyclohexylidenamino, Cyclopentyloxycarbonyl, Cyclohexyloxycarbonyl, Cyclopentylmethoxy, Methyl, Chloro, cyclo through cycloentylmethoxy, methyl, Chloro by cyclylentyl methoxy, methyl, Chloro through cyclo or methyl carbonyl, cyclo or carbonyl by cycloentyl methoxy, cyclo, by cyclopentyl methoxy, cyclo, by cyclo or methyl cyclo, by cyclopentyl methoxy , Ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl or benzyloxycarbonyl,
A ³ also represents pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl,
R ^{4 represents} hydrogen, cyano, hydroxyl, amino, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n-, each optionally substituted by fluorine and / or chlorine. or i-propylamino, dimethylamino, diethylamino, propenyl, butenyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and
R ^{5 represents} hydrogen or methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, Propenyl, butenyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and - only if n stands for the number 0 - also cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine.

The invention particularly relates to compounds of the formula (IA) in which Q, R ¹ , R ² , R ³ , R ⁴ and R ^{5 have} the meanings given above as being particularly preferred.

Compounds of the formula (I) in which
n represents the numbers 0 or 1,
Q represents O (oxygen) or S (sulfur),
R ^{1 represents} fluorine,
R ^{2 represents} cyano,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond or the group -NA ⁴ -, in which A ^{4 represents} hydrogen or methyl,
A ^{2 represents} a single bond, represents O (oxygen) or SO ₂ ,
A ^{3 represents} fluorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, propenyl, butenyl, propynyl or butynyl ,
R ^{4 represents} hydrogen, amino, methyl, ethyl, n- or i-propyl, methylamino, ethylamino or n- or i-propylamino,
R ^{5 represents} hydrogen, methyl, ethyl, n- or i-propyl, propenyl, butenyl, propynyl or butynyl.

The radicals listed above or listed in preferred areas definitions apply to both the end products of the formula (I) and (IA) and ent speaking for the respective output or intermediate required for production Products. These residual definitions can be among themselves, that is, between the given preferred areas can be combined as desired.

Particularly preferred examples of the compounds of the invention Formulas (I) and (IA) are listed in the groups below.

Group 1

Ar has, for example, the meanings listed below:
2-fluoro-4-cyano-phenyl, 2-chloro-4-cyano-phenyl, 3-fluoro-4-cyano-phenyl, 3-chloro-4-cy ano-phenyl, 2-fluoro-5-chloro-4 -cyano-phenyl, 2,5-dichloro-4-cyano-phenyl, 2-chloro-5-fluoro-4-cy ano-phenyl, 2-chloro-4,5-dicyano-phenyl, 2-chloro-4- fluoro-5-cyano-phenyl, 2, 5-difluoro-4-cyano-phenyl, 2-chloro-4-cyano-5-methyl-phenyl, 2-fluoro-4-cyano-5-methyl-phenyl, 2 -Chloro-4-cyano-5-trifluoromethyl-phenyl, 2-fluoro-4-cyano-5-trifluoromethyl-phenyl, 2,5-difluoro-4-thiocarbamoyl-phenyl, 2-fluoro-4-cyano-5- methoxy-phenyl, 2-fluoro-4-cyano-5-i-propoxy-phenyl, 2-chloro-4-cyano-5- (2-propynyloxy) phenyl, 2-fluoro-4-cyano-5- ( 1-methyl-2-propynyloxy) phenyl, 2-chloro-4-thiocarb amoyl-5-i-propoxyphenyl, 2-fluoro-4-cyano-5- (2-propenyloxy) phenyl, 2-chloro 4-cy ano-5-methylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-ethylsulfonylamino-phenyl, 2-fluoro-4-thiocarbamoyl-5-methylsulfonylamino-phenyl, 2-chloro-4-cyano-5-ethylsul fonylamino-phenyl, 2-fluoro-4-cyano-5-cyclopropylsulfonylamino-phenyl, 2-fluoro-4-cy ano-5-i-propylsulfonylamino- phenyl, 2-chloro-4-thiocarbamoyl-5-ethylsulfonylamino-no-phenyl, 2-chloro-4-cyano-5-cyanamino-phenyl, 2-fluoro-4-cyano-5-trifluoromethyl sulfonylamino-phenyl, 2-fluoro- 4-cyano-5- (2,2-difluoroethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5-phenylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-t-butylsulfonylamino no-phenyl, 2-chlorine -4-cyano-5-methoxycarbonyl-phenyl, 2-fluoro-4-cyano-5-ethoxy carbonyl-phenyl, 2-fluoro-4-thiocarbamoyl-5-methoxycarbonyl-phenyl, 2-fluoro-4-cy ano-5 - (1-methyl-2-propynylthio) phenyl, 2-fluoro-4-cyano-5-methylamino-phenyl, 2-chloro-4-thlocarbamoyl-5-methoxycarbonylmethyl-phenyl, 2-chloro-4-cyano-5 - (N-methyl-sulfonylamino) phenyl, 2-chloro-4-cyano-5-i-propoxycarbonylphenyl, 2-fluoro-4-cyano-5- (bis-ethylsulfonylamino) phenyl, 2- Fluoro-4-cyano-5- (N-methylsulfonyl-N-ethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (1-methoxycarbonyl-ethoxy) -phenyl, 2-fluoro-4-cyano- 5-cyclopropyloxy-phenyl, 2-chloro-4-cyano-5-dimethylamino-phenyl, 2-fluoro-4-cyano-5-tetrahydrofurylmethoxy-phenyl, 2-fluoro-4 -cyano-5-aminophenyl, 2-fluoro-4-cyano-5-methylaminocarbonyl-phenyl, 2-fluoro-4-cyano-5-methylsulfonyloxy-phenyl, 2-chloro-4-cyano-5-difluoromethoxy -phenyl, 2-fluoro-4-cy ano-5-ethoxycarbonylmethoxy-phenyl, 2-fluoro-4-cyano-5-dimethylaminocarbonyl-phenyl, 2-fluoro-4-cyano-5-cyanomethoxy-phenyl, 2-fluorine -4-cyano-5- (2-chloro-2-pro penyloxy) phenyl, 2-fluoro-4-cyano-5-hydroxyphenyl, 2-fluoro-4-cyano-5-nitro-phenyl, 2 -Fluoro-4-cyano-5-diethoxyphosphorylamino-phenyl, 2-fluoro-4-cyano-5-chlorosulfonyl-phenyl, 2-fluoro-4-cyano-5-formylamino-phenyl, 2-chloro-4- cyano-5-ethoxy carbonyloxy-phenyl, 2-fluoro-4-cyano-5-diethoxyphosphorylmethoxy-phenyl, 2-chloro-4-cyano-5-hydroxy-phenyl, 2-fluoro-4-cyano-5- (N, N-diacetylamino) phenyl, 2-fluoro-4-cyano-5-acetylamino-phenyl, 2-chloro-4-cyano-5-thiocyanato-phenyl, 2-fluoro-4-cyano-5-diethylaminooxy-phenyl , 2-fluoro-4-cyano-5-tetrahydrofuryloxy-phenyl, 2-fluoro-4-cyano-5-ureido-phenyl, 2-fluoro-4-cyano-5-dimethoxymethyleneamino-phenyl, 2-chloro-4-cyano -5-ethoxymethylene amine o-phenyl, 2-fluoro-4-cyano-5- (2-chloro-ethoxy carbonyloxy) phenyl, 2-chloro-4-cyano-5-dimethylaminomethyleneamino-phenyl, 2-chloro-4-cyano-5- ( perhydropyran-4-yloxy) phenyl, 2-fluoro-4-cyano-5- (2-methoxycar bonyl-ethyl) phenyl, 2-chloro-4-cyano-5- (2-carboxy-2-chloro-ethyl) ) -phenyl, 2-fluoro-4-cy ano-5- (2-chloro-2-methoxycarbonyl-ethyl) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-s-bu toxycarbonyl ) -phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-carbamoyl-ethyl) -phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-methoxycarbonyl-1-methyl -ethyl) -phenyl, 2-fluoro-4-cya no-5- (1,2-dibromo-2-methoxycarbonyl-ethyl) -phenyl, 2-chloro-4-cyano-5- (2-chloro-2- i-pro poxy-carbonyl-ethyl) phenyl, 2-fluoro-4-cyano-5- (2-carboxy-2-chloroethyl) phenyl, 2-fluoro-4-cyano-5- (2-chloro -2-ethylaminocarbonyl-ethyl) -phenyl, 2-fluoro-4-cyano-5- (2-allylaminocarbonyl-2-chloro-ethyl) -phenyl, 2-fluoro-4-cyano-5- (2-ethoxycarbonylethenyl ) -phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-cyclopropylaminocarbonyl-ethyl) -phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-dimethylaminocarbonyl-ethyl) -phenyl, 2-chloro-4-cy ano-5- (2-chloro-2-ethylsulfonylaminocarbonyl-ethyl) -phenyl, 2-fluoro-4-thiocarbamoyl-5- (2-ethylaminocarbonyl-ethenyl) -phenyl, 2 -Fluoro-4-cyano-5- (1-ethoxycarbonyl-ethyl) phenyl, 2-chloro-4-cyano-5- (1-ethoxycarbonylethyl) phenyl, 2-chloro-4-cyano-5-car boxy -phenyl, 2-fluoro-4-cyano-5-i-butoxy-phenyl, 2-chloro-4-cyano-5-i-butoxy-phenyl, 2-chloro-4-cyano-5- (2-methoxy -ethoxy) phenyl.

Group 2

Ar has, for example, the meanings listed in Group 1.

Group 3

Ar has, for example, the meanings listed in Group 1.

Group 4

Ar has, for example, the meanings listed in Group 1.

Group 5

Ar has, for example, the meanings listed in Group 1.

Group 6

Ar has, for example, the meanings listed in Group 1.

Group 7

Ar has, for example, the meanings listed in Group 1.  

Group 8

Ar has, for example, the meanings listed in Group 1.

Group 9

Ar has, for example, the meanings listed in Group 1.

Group 10

Ar has, for example, the meanings listed in Group 1.

Group 11

Ar has, for example, the meanings listed in Group 1.  

Group 12

Ar has, for example, the meanings listed in Group 1.

Group 13

Ar has, for example, the meanings listed in Group 1.

Group 14

Ar has, for example, the meanings listed in Group 1.

Group 15

Ar has, for example, the meanings listed in Group 1.  

Group 16

Ar has, for example, the meanings listed in Group 1.

Group 17

Ar has, for example, the meanings listed in Group 1.

Group 18

Ar has, for example, the meanings listed in Group 1.

Group 19

Ar has, for example, the meanings listed in Group 1.  

Group 20

Ar has, for example, the meanings listed in Group 1.

Group 21

Ar has, for example, the meanings listed in Group 1.

Group 22

Ar has, for example, the meanings listed in Group 1.  

Group 23

Ar has, for example, the meanings listed in Group 1.

Group 24

Ar has, for example, the meanings listed in Group 1.

Group 25

Ar has, for example, the meanings listed in Group 1.

Group 26

Ar has, for example, the meanings listed in Group 1.  

Group 27

Ar has, for example, the meanings listed in Group 1.

Group 28

Ar has, for example, the meanings listed in Group 1.

Group 29

Ar has, for example, the meanings listed in Group 1.

Group 30

Ar has, for example, the meanings listed in Group 1.  

Group 31

Ar has, for example, the meanings listed in Group 1.

Group 32

Ar has, for example, the meanings listed in Group 1.

Group 33

Ar has, for example, the meanings listed in Group 1.

Group 34

Ar has, for example, the meanings listed in Group 1.  

Group 35

Ar has, for example, the meanings listed in Group 1.

Group 36

Ar has, for example, the meanings listed in Group 1.

Group 37

Ar has, for example, the meanings listed in Group 1.

Group 38

Ar has, for example, the meanings listed in Group 1.  

Group 39

Ar has, for example, the meanings listed in Group 1.

Group 40

Ar has, for example, the meanings listed in Group 1.

Group 41

Ar has, for example, the meanings listed in Group 1.

Group 42

Ar has, for example, the meanings listed in Group 1.  

Group 43

Ar has, for example, the meanings listed in Group 1.

Group 44

Ar has, for example, the meanings listed in Group 1.

Group 45

Ar has, for example, the meanings listed in Group 1.

Group 46

Ar has, for example, the meanings listed in Group 1.  

Group 47

Ar has, for example, the meanings listed in Group 1.

Group 48

Ar has, for example, the meanings listed in Group 1.

Group 49

Ar has, for example, the meanings listed in Group 1.

Group 50

Ar has, for example, the meanings listed in Group 1.  

Group 51

Ar has, for example, the meanings listed in Group 1.

Group 52

Ar has, for example, the meanings listed in Group 1.

Group 54

Ar has, for example, the meanings listed in Group 1.

Group 55

Ar has, for example, the meanings listed in Group 1.  

Group 56

Ar has, for example, the meanings listed in Group 1.

Group 57

Ar has, for example, the meanings listed in Group 1.

Group 58

Ar has, for example, the meanings listed in Group 1.

Group 59

Ar has, for example, the meanings listed in Group 1.  

Group 60

Ar has, for example, the meanings listed in Group 1.

Group 61

Ar has, for example, the meanings listed in Group 1.

Group 62

Ar has, for example, the meanings listed in Group 1.

Group 63

Ar has, for example, the meanings listed in Group 1.  

Group 64

Ar has, for example, the meanings listed in Group 1.

Group 65

Ar has, for example, the meanings listed in Group 1.

Group 66

Ar has, for example, the meanings listed in Group 1.

Group 67

Ar has, for example, the meanings listed in Group 1.  

Group 68

Ar has, for example, the meanings listed in Group 1.

Group 69

Ar has, for example, the meanings listed in Group 1.

Group 70

Ar has, for example, the meanings listed in Group 1.

Group 71

Ar has, for example, the meanings listed in Group 1.

Group 72

Ar has, for example, the meanings listed in Group 1.

Group 73

Ar has, for example, the meanings listed in Group 1.

Group 74

Ar has, for example, the meanings listed in Group 1.

Group 75

Ar has, for example, the meanings listed in Group 1.  

Group 76

Ar has, for example, the meanings listed in Group 1.

Group 77

Ar has, for example, the meanings listed in Group 1.

Group 78

Ar has, for example, the meanings listed in Group 1.

Group 79

Ar has, for example, the meanings listed in Group 1.  

Group 80

Ar has, for example, the meanings listed in Group 1.

Group 81

Ar has, for example, the meanings listed in Group 1.

Group 82

Ar has, for example, the meanings listed in Group 1.

Group 83

Ar has, for example, the meanings listed in Group 1.  

Group 84

Ar has, for example, the meanings listed below.

Group 85

Ar has, for example, the meanings listed below.

Group 86

Ar has, for example, the meanings listed in Group 1.

Group 87

Ar has, for example, the meanings listed in Group 1.  

Group 88

Ar has, for example, the meanings listed in Group 1.

Group 89

Ar has, for example, the meanings listed in Group 1.

Group 90

Ar has, for example, the meanings listed in Group 1.

Group 91

Ar has, for example, the meanings listed in Group 1.  

Group 92

Ar has, for example, the meanings listed in Group 1.

Group 93

Ar has, for example, the meanings listed in Group 1.

Group 94

Ar has, for example, the meanings listed in Group 1.

Group 95

Ar has, for example, the meanings listed in Group 1.  

Group 96

Ar has, for example, the meanings listed in Group 1.

Group 97

Ar has, for example, the meanings listed in Group 1.

Group 98

Ar has, for example, the meanings listed in Group 1.

Group 99

Ar has, for example, the meanings listed in Group 1.  

Group 100

Ar has, for example, the meanings listed in Group 1.

Group 101

Ar has, for example, the meanings listed in Group 1.

Group 102

Ar has, for example, the meanings listed in Group 1.

Group 103

Ar has, for example, the meanings listed in Group 1.  

Group 104

Ar has, for example, the meanings listed in Group 1.

Group 105

Ar has, for example, the meanings listed in Group 1.

Group 106

Ar has, for example, the meanings listed in Group 1.

Group 107

Ar has, for example, the meanings listed in Group 1.

Group 108

Ar has, for example, the meanings listed in Group 1.

Group 109

Ar has, for example, the meanings listed in Group 1.

Group 110

Ar has, for example, the meanings listed in Group 1.

Group 111

Ar has, for example, the meanings listed in Group 1.

Group 112

Ar has, for example, the meanings listed in Group 1.  

Group 113

Ar has, for example, the meanings listed in Group 1.

Group 114

Ar has, for example, the meanings listed in Group 1.

Group 115

Ar has, for example, the meanings listed in Group 1.

Group 116

Ar has, for example, the meanings listed in Group 1.  

Group 117

Ar has, for example, the meanings listed in Group 1.

Group 118

Ar has, for example, the meanings listed in Group 1.

Group 119

Ar has, for example, the meanings listed in Group 1.

Group 120

Ar has, for example, the meanings listed in Group 1.  

Group 121

Ar has, for example, the meanings listed in Group 1.

Group 122

Ar has, for example, the meanings listed in Group 1.

Group 123

Ar has, for example, the meanings listed in Group 1.

Group 124

Ar has, for example, the meanings listed in Group 1.

Group 125

Ar has, for example, the meanings listed in Group 1.

Group 126

Ar has, for example, the meanings listed in Group 1.

Group 127

Ar has, for example, the meanings listed in Group 1.

Group 128

Ar has, for example, the meanings listed in Group 1.

Group 129

Ar has, for example, the meanings listed in Group 1.  

Group 130

Ar has, for example, the meanings listed in Group 1.

Group 131

Ar has, for example, the meanings listed in Group 1.

Group 132

Ar has, for example, the meanings listed in Group 1.

Group 133

Ar has, for example, the meanings listed in Group 1.  

Group 134

Ar has, for example, the meanings listed in Group 1.

Group 135

Ar has, for example, the meanings listed in Group 1.

Group 136

Ar has, for example, the meanings listed in Group 1.

Group 137

Ar has, for example, the meanings listed in Group 1.  

Group 138

Ar has, for example, the meanings listed in Group 1.

Group 139

Ar has, for example, the meanings listed in Group 1.

Group 140

Ar has, for example, the meanings listed in Group 1.

Group 141

Ar has, for example, the meanings listed in Group 1.  

Group 142

Ar has, for example, the meanings listed in Group 1.

Group 143

Ar has, for example, the meanings listed in Group 1.

Group 144

Ar has, for example, the meanings listed in Group 1.

Group 145

Ar has, for example, the meanings listed in Group 1.  

Group 146

Ar has, for example, the meanings listed in Group 1.

Group 147

Ar has, for example, the meanings listed in Group 1.

Group 148

Ar has, for example, the meanings listed in Group 1.

Group 149

Ar has, for example, the meanings listed in Group 1.  

Group 150

Ar has, for example, the meanings listed in Group 1.

Group 151

Ar has, for example, the meanings listed in Group 1.

Group 152

Ar has, for example, the meanings listed in Group 1.

Group 153

Ar has, for example, the meanings listed in Group 1  

Group 154

Ar has, for example, the meanings listed in Group 1.

Group 155

Ar has, for example, the meanings listed in Group 1.

Group 156

Ar has, for example, the meanings listed in Group 1.

Group 157

Ar has, for example, the meanings listed in Group 1.  

Group 158

Ar has, for example, the meanings listed in Group 1.

Group 159

Ar has, for example, the meanings listed in Group 1.

Group 160

Ar has, for example, the meanings listed in Group 1.

Group 161

Ar has, for example, the meanings listed in Group 1.

Group 162

Ar has, for example, the meanings listed in Group 1.

Group 163

Ar has, for example, the meanings listed in Group 1.

Group 164

Ar has, for example, the meanings listed in Group 1.

Group 165

Ar has, for example, the meanings listed in Group 1.

Group 166

Ar has, for example, the meanings listed in Group 1.  

Group 167

Ar has, for example, the meanings listed in Group 1.

Group 168

Ar has, for example, the meanings listed in Group 1.

Group 169

Ar has, for example, the meanings listed in Group 1.

Group 170

Ar has, for example, the meanings listed in Group 1.  

Group 171

Ar has, for example, the meanings listed in Group 1.

Group 172

Ar has, for example, the meanings listed in Group 1.

Group 173

Ar has, for example, the meanings listed in Group 1.

Group 174

Ar has, for example, the meanings listed in Group 1.

Group 175

Ar has, for example, the meanings listed in Group 1.

Group 176

Ar has, for example, the meanings listed in Group 1.

Group 177

Ar has, for example, the meanings listed in Group 1.

Group 178

Ar has, for example, the meanings listed in Group 1.

Group 179

Ar has, for example, the meanings listed in Group 1.  

Group 180

Ar has, for example, the meanings listed in Group 1.

Group 181

Ar has, for example, the meanings listed in Group 1.

Group 182

Ar has, for example, the meanings listed in Group 1.

Group 183

Ar has, for example, the meanings listed in Group 1.  

Group 184

Ar has, for example, the meanings listed in Group 1.

Group 185

Ar has, for example, the meanings listed in Group 1.

Group 186

Ar has, for example, the meanings listed in Group 1.

Group 187

Ar has, for example, the meanings listed in Group 1.  

Group 188

Ar has, for example, the meanings listed in Group 1.

Group 189

Ar has, for example, the meanings listed in Group 1.

Group 190

Ar has, for example, the meanings listed in Group 1.

The new substituted triazinones of the general formula (I) are obtained if oxo-phenylacetic acid derivatives of the general formula (II)

in which
R ¹ , R ² and R ^{3 have} the meaning given above and
R 'represents alkyl,
with carbonic acid derivatives of the general formula (III)

in which
Q and R ^{4 have} the meaning given above,
if appropriate in the presence of a diluent and if appropriate subsequently the compounds of the formulas (IB) and / or (IC) thus obtained

with compounds of the general formula (IV)

XR ⁵ (IV)

in which
R ^{5 has} the meaning given above and
X represents halogen,
or with compounds of the general formula (V)

R ⁵ -O-SO ₂ -OR ⁵ (V)

in which
R ^{5 has} the meaning given above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, subsequently on the compounds of the general formula (I) thus obtained, as part of the definition of the substituent, carries out further substitution reactions in the customary manner.

In principle, the compounds of the general formula (I) can also be synthesized as shown schematically below:
Reaction of oxo-phenylacetic acid derivatives of the general formula (II) with thionyl chloride, amines and hydrazine, then reaction of the resulting hydrazone amides of the general formula (VI) with carbonic acid derivatives of the general formula (VII) - where Q, R ¹ , R ² , R ³ and R ^{4 have} the meaning given above, R 'is alkyl (in particular methyl or ethyl) and Y ¹ and Y ^{2 are} halogen (in particular chlorine), alkoxy (in particular methoxy or ethoxy) or phenoxy:

Reaction of oxo-phenylacetic acid derivatives of the general formula (II) with formylhydrazine and esters of the general formula (VII), then reaction of the acylhydrazone esters of the general formula (VIII) thus obtained with amino compounds of the general formula (IX) - where R ¹ , R ² , R ³ and R ^{4 have} the meaning given above and R 'represents alkyl (in particular methyl or ethyl):

If, for example, 2- (4-cyano-2,5-difluorophenyl) -2-oxo-acetic acid methyl ester and 4-ethyl-thiosemicarbazide are used as starting materials, the reaction sequence in the process according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the oxo-phenylacetic acid derivatives to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I). In the formula (II), R ¹ , R ² and R ³ have preferably or in particular those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention, preferably or as particularly preferred for R ¹ , R ² and R ^{3 have been} given; R 'is preferably C ₁ -C ₄ alkyl, especially methyl or ethyl.

The starting materials of the general formula (II) are not yet from the literature known; as new substances, they are also the subject of the present application.  

The new oxo-phenylacetic acid derivatives of the general formula (II) are obtained if

• (α) nitro- or cyano-phenylacetic acid derivatives of the general formula (X)
  in which
  R ¹ , R ² and R ^{3 have} the meaning given above,
  R 'represents alkyl (especially methyl or ethyl), and
  Z represents nitro or cyano,
  with oxidizing agents, such as. B. chromic anhydride, optionally in the presence of diluents, such as. B. acetic acid and acetonitrile, at temperatures between 0 ° C and 80 ° C (see. The preparation examples),
  or if you
• (β) benzoyl cyanides of the general formula (XI)
  in which
  R ¹ , R ² and R ^{3 have} the meaning given above,
  with alcohols such as B. with methanol or ethanol, in the presence of acids, such as. B. sulfuric acid or methanesulfonic acid, at temperatures between 0 ° C and 100 ° C.

The nitro or cyano-phenylacetic acid derivatives to be used as precursors general formula (X) are not yet known from the literature; they are as new Substances are also the subject of the present application.

The new nitro- or cyano-phenylacetic acid derivatives of the general formula (X) are obtained if nitro- or cyano-acetic acid derivatives of the general formula (XII)

in which
R 'and Z have the meaning given above,
with halobenzene derivatives of the general formula (XIII)

in which
R ¹ , R ² and R ^{3 have} the meaning given above and
X ^{1 represents} halogen (in particular fluorine, chlorine or bromine),
in the presence of a basic compound such as e.g. As sodium ethylate, and in the presence of a diluent, such as. As ethanol, at temperatures between 10 ° C and 120 ° C (see. J. Chem. Soc. 1927, 46-50, preparation examples).

The benzoyl cyanides of the general use which may be used as precursors Formula (M) are also not yet known from the literature; they are as new Substances are also the subject of the present application.

The new benzoyl cyanides of the general formula (XI) are obtained if benzoyl halides of the general formula (XIV)

in which
R ¹ , R ² and R ^{3 have} the meaning given above and
X ^{2 represents} halogen (especially chlorine),
reacted with trimethylsilyl cyanide at temperatures between 10 ° C and 150 ° C (cf. the preparation examples).

The process according to the invention for the preparation of the compounds of the general Formula (I) is preferably carried out using a diluent leads. In addition to water, the main diluents here are inert organic solvents. These include in particular aliphatic, ali cyclic or aromatic, optionally halogenated hydrocarbons, such as for example gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petrol ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ether, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol di  methyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethyl form amide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexa methylphosphoric triamide; Esters such as methyl acetate or ethyl acetate esters, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-Pro panol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

The process according to the invention is generally carried out under normal pressure leads. However, it is also possible to increase the process according to the invention or reduced pressure - generally between 0.1 bar and 10 bar to lead.

To carry out the process according to the invention, the starting materials in generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The The reaction is generally carried out in a suitable diluent and the reaction mixture is generally required for several hours stirred temperature. The workup is carried out using customary methods led (see the manufacturing examples).

The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are found in places grow where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used.  

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, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ainbrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, 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.

Monocotyledonous weeds of the genera

Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops, Phalaris.

Monocot cultures of the genera

Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

The use of the active compounds according to the invention is by no means limited to these Limited genres, but extends in the same way to others Plants.

The active compounds according to the invention are suitable depending on the con center for total weed control, e.g. B. on industrial and track systems and on Because of and places with and without tree cover. Likewise, the fiction active agents for weed control in permanent crops, e.g. B. Forst, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm,  Cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture areas and for selective weed control in annual crops become.

The compounds of formula (I) according to the invention show strong herbicidal activity solvency and a wide range of effects when used on and on the floor aerial parts of plants. To a certain extent, they are also suitable for selective use Control of monocot and dicot weeds in monocot and di cotyledon cultures, both pre-emergence and post-emergence.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, sol Liche powder, granules, suspension emulsion concentrates, impregnated with active ingredient Natural and synthetic substances as well as very fine encapsulation in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, if necessary using surface-active agents, that is Emulsifiers and / or dispersants and / or foaming agents.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane 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 such as dimethylformamide and dimethyl sulfoxide, and water.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont  morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, come as solid carriers for granules in question: e.g. B. broken and fractionated natural rocks such as calcite, marble, Pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules made of organic material such as sawdust, Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam Generating funds are possible: z. B. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants come into question: z. B. lignin sulfite 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 phospho lipids 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 substances 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  Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, benazolin (-ethyl), benturesate, bensulfuron (-methyl), bentazone, B enzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromo butides, bromofenoxim, bromoxynil, butachlor, butroxydim, butylates, cafenstrole, Caloxydim, carbetamides, carfentrazone (-ethyl), chloromethoxyfen, chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cini don (-ethyl), cinmethylin, cinosulfuron, clethodim, clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyanazines, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalo fop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (- methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, di mefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, etobenzanide, fenoxaprop (-P-ethyl), flamprop (-isopropyl), Flam prop (-isopropyl-L), flamprop (-methyl), flazasulfuron, fluazifop (-P-butyl), fluazo latex, flucarbazone, flufenacet, flumetsulam, flumiclorac (-pentyl), flumioxazin, Flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), Flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthi amides, fomesafen, glufosinate (-ammonium), glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imaza methabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, Imazethapyr, imazosulfuron, iodosuhuron, ioxynil, isopropalin isoproturon, isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiaz uron, metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop amides, neburon, nicosulfuron, nofflurazon, orbencarb, oryzalin, oxadiargyl, oxa diazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendi methalin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron (-methyl),  Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyz amides, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolates, pyrazosulfuron (ethyl), Pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefuryl), rimsulfuron, sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthi uron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazo pyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Triflusulfuron.

A mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellants, plant nutrients substances and soil structure improvement agents is 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 Solutions, suspensions, emulsions, powders, pastes and granules are used become. The application is done in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after emergence of the plants are applied. They can also be planted in the soil before sowing be working.

The amount of active ingredient used can vary over a wide range. she depends essentially on the type of effect desired. In general the application rates are between 1 g and 10 kg of active ingredient per hectare of soil area, preferably between 5 g and 5 kg per ha.

The manufacture and use of the active compounds according to the invention are based on following examples.

Manufacturing examples

example 1

10.6 g (0.10 mol) of thiocarbodihydrazide in 50 ml of water at 90 ° C to Formation of a clear solution stirred, then with 24 g (0.10 mol) of 2- (4-cyano-2,5-di fluorophenyl) -2-oxo-acetic acid ethyl ester and 40 minutes at 110 ° C. touched. The precipitated reaction product is cold suctioned off with water wash and dried.

15 g (53% of theory) of 6- (4-cyano-2,5-difluorophenyl) -4-ami are obtained no-5-oxo-3-thioxo-1,2,4-triazine, melting point 195 ° C.

Example 2

10.5 g (0.10 mol) of 4-methyl-thiosemicarbazide in 250 ml of water at 100 ° C to stirred to form a clear solution, then with 23.9 g (0.10 mol) of 2- (4-Cy ano-2,5-difluorophenyl) -2-oxo-acetic acid ethyl ester added, at 12 hours Stirred at 100 ° C, filtered off cold product and dried. The residue is in 150 ml of N, N-dimethylformamide with 4 g (0.1 mol) of sodium hydroxide 12 Stirred for hours at room temperature (about 20 ° C), then mixed with 300 ml of water, with conc. Acidified hydrochloric acid, filtered off the precipitated product, ge with water wash and dried.

22.3 g (80% of theory) of 6- (4-cyano-2,5-difluorophenyl) -4-me are obtained thyl-5-oxo-3-thioxo-1,2,4-triazine, melting point 191 ° C.  

Example 3

2.8 g (10 mmol) of 6- (4-cyano-2,5-difluorophenyl) -4-methyl-5-oxo-3-thioxo-1,2,4-tri Become azine with 2.8 g (20 mmol) of potassium carbonate and 1.3 g (12 mmol) of ethane sulfonic acid amide in 100 ml of dimethyl sulfoxide stirred at 135 ° C for 12 hours finally concentrated, the residue stirred with water, with conc. Hydrochloric acid acidifies, suction filtered, washed with water and dried. For cleaning with Chromatograph cyclohexane / ethyl acetate (vol .: 7: 1) over silica gel.

1.3 g (35% of theory) of 6- (4-cyano-5-ethylsulfonylamino-2-fluorophe) are obtained nyl) -4-methyl-5-oxo-3-thioxo-1,2,4-triazine with a melting point of 203 ° C.

Example 4

1.5 g (4 mmol) of 6- (4-cyano-5-ethylsulfonylamino-2-fluorophenyl) -4-methyl-5-oxo-3-thi oxo-1,2,4-triazine are mixed with 1.1 g (8 mmol) of potassium carbonate, 0.5 g (4.2 mmol) Dimethyl sulfate in 50 ml acetonitrile for 12 hours at room temperature (approx. 20 ° C) stirred, then concentrated, the residue stirred with water, with conc. Salt acidified, precipitated product filtered off, washed with water and ge dries. For cleaning with cyclohexane / ethyl acetate (vol .: 3: 1) Chromatographed silica gel.  

0.4 g (26% of theory) of 6- (4-cyano-5-ethylsulfonylamino-2-fluorophe) is obtained nyl) -2,4-dimethyl-5-oxo-3-thioxo-1,2,4-triazine, melting point 207 ° C.

Example 5

1.0 g (2.7 mmol) (4-cyano-5-ethylsulfonylamino-2-fluorophenyl) -4-amino-5-oxo-3-thi oxo-1,2,4-triazine are mixed with 0.74 g (5.4 mmol) of potassium carbonate, 0.43 g (3 mmol) Methyl iodide in 50 ml acetonitrile stirred for 12 hours at room temperature (approx. 20 ° C), then concentrated, the residue stirred with water, with conc. Hydrochloric acid acidified, precipitated product suction filtered, washed with water and dried. For purification, the product is recrystallized from methanol.

0.3 g (29% of theory) of 6- (4-cyano-5-ethylsulfonylamino-2-fluorophe) is obtained nyl) -3-methylthio-4-amino-5-oxo-1,2,4-triazine, melting point 213 ° C.

Example 6

1.1 g (2.9 mmol) of 6- (4-cyano-5-ethylsulfonylamino-2-fluorophenyl) -3-methylthio-4-me thyl-5-oxo-1,2,4-triazine in 30 ml of methanol with 1.8 g of 30% sodium methylate solution and mixed with 1.2 g (8.7 mmol) of methyl iodide and at 12 hours  Reflux temperature stirred. After concentration, the residue is mixed with water stirs, with conc. Acidified hydrochloric acid, suction filtered, washed with water and ge dries.

0.3 g (27% of theory) of 6- [4-cyano-5- (N-methyl-N-ethylsulfonylamino) -2-fluorophe are obtained nyl] -3-methoxy-4-methyl-5-oxo-1,2,4-triazine, melting point 72 ° C.

Analogously to Examples 1 to 6 and in accordance with the general description of Manufacturing processes according to the invention can also be carried out in the following Compounds of formula (I) or formula (IA) listed in Table 1 are prepared become.

Table 1

Examples of the compounds of the formula (I) or of the formula (A)

Starting materials of formula (II)

Example (II-1)

75 g (0.30 mol) of 2- (4-cyano-2,5-difluorophenyl) -2-cyano-acetic acid ethyl ester are placed in 320 ml of acetonitrile and 80 ml of acetic acid and with 130 g (1.3 mol) Chromic anhydride added. The mixture heats up to 32 ° C. To Heating to 50 ° C, the temperature is ge by occasional cooling at 50 ° C hold. After the reaction has subsided, stirring is continued for 30 minutes, diluted with 1 liter of water and extracted with methylene chloride. The organic phase is over Dried sodium sulfate and concentrated.

72 g (93% of theory, purity according to GC-MS: 93%) of 2- (4-cyano-2,4-difluorophenyl) -2-oxo-acetic acid ethyl ester are obtained.
H ¹ -NMR (CDCl ₃ ): 1.42-1.44; 4.43-4.50; 7.49-7.54; 7.72-7.77 ppm.

Analogously to Example (II-1), the following formula is also obtained:

H ¹ -NMR (CDCl ₃ ): 1.31-1.35; 4.40-4.47; 7.45-7.63 ppm.

Starting materials of formula (X)

Example (X-1)

40 g (1.0 mol) of sodium hydroxide powder are in 400 ml of N, N-dimethylformamide submitted and at 10 ° C (cooling) is added dropwise 113 g (1.0 mol) of ethyl cyanoacetate ester too. Then a solution of 79 g (0.5 mol) of 2,4,5-trifluoro-benzonitrile added dropwise in 100 ml of N, N-dimethylformamide at a maximum of 25 ° C. (cooling) and 30 Stirred minutes at 25 ° C. After concentration, the residue is in water recorded with conc. Acidified hydrochloric acid, extracted with dichloromethane, the organic phase dried over sodium sulfate and concentrated.

125 g (98% of theory, purity according to GC-MS: 98% strength) of (2-cyano-2,5-difluorophenyl) -2-cyano-acetic acid ethyl ester are obtained as an oil.
H ¹ -NMR (CDCl ₃ ): 1.31-1.36; 4.30-4.37; 5.06; 7.45-7.49 ppm.

Analogously to Example (X-1), the following compounds of the formula (Xa) are also obtained:

Starting materials of the formula (XI)

Example (XI-1)

21.5 g (0.11 mol) of 4-cyano-2,5-difluoro-benzoyl chloride are added after the addition of 12 g (0.12 mol) of trimethylsilyl cyanide were stirred at the reflux temperature for one hour and then concentrated.

20.2 g are obtained (95% of theory, purity according to GC-MS: 99%) 4-cyano-2,5-difluoro-benzoyl cyanide as an oil.  

Examples of use Example A Pre-emergence test

Solvent: 5 parts by weight of acetone <02595 00070 552 001000280000000200012000285910248400040 0002019835943 00004 02476 / DL < Emulsifier: 1 part by weight of alkylaryl polyglycol ether.

To prepare a suitable preparation of active compound, 1 Ge is mixed 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. After about 24 hours the soil is sprayed with the active ingredient preparation so that the desired one Amount of active ingredient is applied per unit area. The concentration of the spritz broth is chosen so that the desired in 1000 liters of water per hectare Amount of active ingredient is applied.

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 compounds according to Preparation Example 3 show 8, 12, 15 and 16 with good tolerance to crops, such as e.g. B. corn, wheat and soybeans, strong activity against weeds.  

Example B Post 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, mix 1 Part by weight of active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5-15 cm have so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l water / ha the desired amounts of active ingredient are applied.

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 compounds according to Preparation Example 2 show 3, 4, 5 8, 10, 12, 13, 16, 17, 21 and 22 with partially good tolerance to Cultivated plants, such as. B. wheat, barley, rapeseed and sugar beet, strong effect against weeds.

Claims (10)

1. Substituted triazinones of the general formula (I)
in which
n represents the numbers 0 or 1,
Q represents O (oxygen), S (sulfur), NH or N (alkyl),
R ^{1 represents} hydrogen or halogen,
R ^{2 represents} cyano, carbamoyl or thiocarbamoyl,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, alkyl, alkenyl, Alkynyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
A ¹ furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A ^{2 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, alkyl, alkoxy, Aryl, alkyl sulfonyl or arylsulfonyl,
A ² furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A ^{3 represents} hydrogen with the proviso that in this case A ¹ and / or A ² do not represent a single bond if R ^{1 represents} hydrogen,
A ³ furthermore for hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio, alkyl sulfinyl, alkylsulfonyl, alkylamino which are optionally substituted by halogen or alkoxy, Dialkylamino, alkoxy carbonyl or dialkoxy (thio) phosphoryl, for each alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl, optionally substituted by halogen, for each optionally halogen, cyano, carboxy, alkyl and / or Alkoxy-carbonyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, or for aryl, aryloxy, aralkyl, optionally substituted by nitro, cyano, carboxy, halogen, alkyl, haloalkyl, alkyloxy, haloalkyloxy and / or alkoxycarbonyl , Aryl alkoxy, aryloxycarbonyl or arylalkoxycarbonyl l stands
A ³ furthermore represents in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyrimidinyl or pyrimidinyl
R ^{4 stands} for hydrogen, cyano, hydroxy, amino, or for any alkyl, alkoxy, alkylamino, dialkyl amino, alkenyl, alkynyl or cycloalkyl optionally substituted by halogen, and
R ^{5 stands} for hydrogen or for alkyl, alkenyl, alkynyl or cycloalkyl which is optionally substituted by cyano, halogen, alkoxy or alkoxycarbonyl, and - only in the case where n stands for the number 0 - also cyano, carbamoyl, thiocarbamoyl or halogen ,
and for the case that in the general formula (I) n stands for the number 1, the tautomeric and / or isomeric compounds of the general formula (IA) to the compounds of the formula (I), wherein Q, R ¹ , R ² , R ³ R ⁴ and R ^{5 have} the meaning given above
2. Substituted triazinones according to claim 1, characterized in that
n represents the numbers 0 or 1,
Q represents O (oxygen), S (sulfur), NH or N (C ₁ -C ₄ alkyl),
R ^{1 represents} hydrogen, fluorine, chlorine or bromine,
R ^{2 represents} cyano, carbamoyl or thiocarbamoyl,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, C ₁ -C _6- alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -alkoxy, phenyl, C ₁ -C ₆ -alkylsulfonyl or phenylsulfonyl,
A ¹ furthermore represents in each case optionally fluorine and / or chlorine-substituted C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ aza alkenediyl, C ₂ -C ₆ alkynediyl, C ₃ -C ₆ -cycloalkanediyl, C ₃ -C ₆ - cycloalkenediyl or phenylene,
A ^{2 represents} a single bond, represents O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, C ₁ -C _6- alkyl, C ₁ -C ₆ -alkoxy, phenyl, C ₁ -C ₆ -alkylsulfonyl or phenylsulfonyl,
A ² furthermore represents in each case optionally substituted by fluorine / or chlorine, and C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ aza alkenediyl, C ₂ -C ₆ alkynediyl, C ₃ -C ₆ -cycloalkanediyl, C ₃ -C ₆ - cycloalkenediyl or phenylene,
A ^{3 represents} hydrogen with the proviso that in this case A ¹ and / or A ² do not represent a single bond if R ^{1 represents} hydrogen,
A ³ furthermore for hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for each optionally substituted by fluorine, chlorine or C ₁ -C ₆ alkoxy ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkyl sulfonyl, C ₁ -C ₆ alkylamino, di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₆ alkoxycarbonyl or di (C ₁ -C ₆ alkoxy) - (thio) phosphoryl, each optionally substituted by fluorine and / or chlorine C ₂ -C ₆ alkenyl, CC ₆ alkenyloxy, C ₂ -C ₆ alkenylamino, C ₂ -C ₆ alkylidene amino, C ₂ -C ₆ alkenyloxy carbonyl, C ₂ -C ₆ alkynyl, C ₂ - C ₆ -alkynyloxy, C ₂ -C ₆ -alkynylamino or C ₂ -C ₆ -alkynyloxy-carbonyl, if appropriate by fluorine, chlorine, cyano, carboxy, C ₁ -C ₄ -alkyl and / or C ₁ - C ₄ alkoxy-carbonyl substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyloxy, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ -alkoxy, C ₃ -C ₆ -cycloalkyloxy carbonyl or C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkoxy-carbonyl, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, C ₁ - C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkyloxy, C ₁ -C ₄ haloalkyloxy and / or C ₁ -C ₄ alkoxy carbonyl substituted phenyl, phenyloxy, phenyl-C ₁ - C ₄ -alkyl, phenyl-C ₁ -C ₄ -alkoxy, phenyloxy-carbonyl or phenyl-C ₁ -C ₄ -alkoxy-carbonyl,
A ³ furthermore represents in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridinyl, pyridolyl, pyridinyl
R ^{4 is} hydrogen, cyano, hydroxy, amino, or for C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, C ₁ -C ₆ -alkylamino, di- (optionally substituted by fluorine and / or chlorine C ₁ -C ₄ alkyl) amino, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or C ₃ -C ₆ cycloalkyl, and
R ⁵ represents hydrogen or represents in each case optionally substituted by cyano, fluorine, chlorine, C ₁ -C ₆ alkoxy or C ₁ -C ₆ -alkoxy-carbonyl-substituted C ₁ - C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl or C ₃ -C ₆ cycloalkyl, and - only in the case where n stands for the number 0 - also cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine. 3. Substituted triazinones according to claim 1, characterized in that
n represents the numbers 0 or 1,
Q represents O (oxygen), S (sulfur), NH or N (CH ₃ ),
R ^{1 represents} hydrogen, fluorine or chlorine,
R ^{2 represents} cyano, carbamoyl or thiocarbamoyl,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, represents O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, propenyl, butenyl, propynyl, butinyl, methoxy, ethoxy, n- or i-propoxy, phenyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, or phenylsulfonyl,
A ¹ furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, methyl, ethyl, n- or i-propyl, methoxy , Ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A ² furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ³ for hydrogen, hydroxyl, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl substituted by fluorine, chlorine, methoxy or ethoxy, if appropriate -, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n -, i-, s- or t-pentyloxy, methylthio, ethyl thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methyl sulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl , Ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethyl amino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl , for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylam in each case optionally substituted by fluorine or chlorine ino, propynyloxycarbonyl or butynyloxycarbonyl, for each cyclo propyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl Cyclopropyl methyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexyl methyl, cyclo-propyl methoxy, cyclobutyl methoxy, cyclo pentyl methoxy, cyclohexyl methoxy, cyclopentylidenamino, cyclohexylidenamino, cyclopentyloxycarbonyl, cyclohexyloxy carbonyl, cyclopentyl or methoxy carbonyl, cyclo, nitro, cyclo, methoxy, carbonyl, cyclo, methoxycarbonyl, cyclo, methoxycarbonyl, cyclo, methoxycarbonyl, cyclo, methoxycarbonyl, cyclo, methoxycarbonyl, cyclo, methoxycarbonyl, cyclo, methoxycarbonyl, cyclo, methoxycarbonyl, cyclo, cyclo, or Bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl or benzyloxy carbonyl stands,
A ³ furthermore represents pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thia diazolyl, pyridinyl, pyrimidinyl, triazinyl,
R ⁴ for hydrogen, cyano, hydroxy, amino, or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, which is optionally substituted by fluorine and / or chlorine , n- or i-propylamino, dimethylamino, diethylamino, propenyl, butenyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and
R ^{5 represents} hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, Propenyl, butenyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and - only in the case where n stands for the number 0 - also cyano, carbamoyl, thio carbamoyl, fluorine, chlorine or bromine. 4. Substituted triazinones according to claim 1, characterized in that
n represents the numbers 0 or 1,
Q represents O (oxygen) or S (sulfur),
R ^{1 represents} fluorine,
R ^{2 represents} cyano,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond or the group -NA ⁴ -, in which A ^{4 represents} hydrogen or methyl,
A ^{2 represents} a single bond, represents O (oxygen) or SO ₂ ,
A ^{3 represents} fluorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, t-, s- or t-pentyl, propenyl, butenyl, propynyl or butynyl ,
R ^{4 represents} hydrogen, amino, methyl, ethyl, n- or i-propyl, methylamino, ethylamino or n- or i-propylamino,
R ^{5 represents} hydrogen, methyl, ethyl, n- or i-propyl, propenyl, butenyl, propynyl or butynyl. 5. A process for the preparation of substituted triazinones according to any one of claims 1 to 4, characterized in that derivatives of oxo-phenylacetic acid of the general formula (II)
in which
R ¹ , R ² and R ^{3 have} the meaning given in one of claims 1 to 4 and
R 'represents alkyl,
with carbonic acid derivatives of the general formula (III)
in which
Q and R ^{4 have} the meaning given in one of claims 1 to 4,
if appropriate in the presence of a diluent and, if appropriate, subsequently the compounds of the formulas (IB) and / or (IC) thus obtained
with compounds of the general formula (IV)
XR ⁵ (IV)
in which
R ^{5 has} the meaning given in one of claims 1 to 4 and
X represents halogen,
or with compounds of the general formula (V)
R ⁵ -O-SO ₂ -OR ⁵ (V)
in which
R ^{5 has} the meaning given in one of claims 1 to 4,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, subsequently carries out further substitution reactions in the customary manner on the compounds of the general formula (I) thus obtained as part of the definition of the substituent. 6. oxo-phenylacetic acid derivatives of the general formula (II)
in which
R ¹ , R ² and R ^{3 have} the meaning given in one of claims 1 to 4 and
R 'represents alkyl. 7. Nitro- or cyano-phenylacetic acid derivatives of the general formula (X)
in which
R ¹ , R ² and R ^{3 have} the meaning given in one of claims 1 to 4,
R 'represents alkyl (especially methyl or ethyl), and
Z stands for nitro or cyano. 8. Benzoyl cyanides of the general formula (XI)
in which
R ¹ , R ² and R ^{3 have} the meaning given in one of claims 1 to 4. 9. Use of at least one substituted triazinone according to one of the Claims 1 to 4 for combating undesirable plants. 10. Herbicidal agents, characterized by the content of at least one sub substituted triazinone according to any one of claims 1 to 4 and usual stretch average.