DE10043790A1 - Substituted 1-aryl-pyridin-2- (thi) one - Google Patents

Abstract

The invention relates to 1-aryl-pyridin-2-(thi)ones of general formula (I), wherein Q represents O (oxygen) or S (sulfur), R<1> represents halogen, R<2> represents cyano, carbamoyl, thiocarbamoyl, halogen or optionally substitued alkyl, alkoxy or arylalkoxy, respectively, R<3> has the meaning given in the description, X<1> represents hydrogen, halogen or optionally substituted alkyl, X<2 > represents halogenalkyl and X<3> represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen or optionally substituted alkyl or alkoxycarbonyl; to methods and intermediate products for producing these compounds and to their use as selective herbicides.

Description

The invention relates to new substituted 1-aryl-pyridin-2- (thi) ones, processes and new intermediates for their manufacture and their use as plants treatment agents, in particular as herbicides.

It is known that certain substituted 1-aryl-pyridin-2-ones are herbicidal or in have secticidal properties (cf. DE-A-28 30 700, EP-A-216541, EP-A-259048, EP-A-488220, US-A-3711488, US-A-3838155, US-A-4394156). This ver However, bonds have so far had no significant significance.

The new substituted 1-aryl-pyridin-2- (thi) ones of the general formula (I)

in which
Q represents O (oxygen) or S (sulfur),
R ^{1 represents} halogen,
R ^{2 represents} cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy or arylalkoxy,
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 -N (A ⁴ ) -, wherein A ^{4 represents} hydrogen, hydroxy, or represents in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, aryl or arylsulfonyl,
A ¹ furthermore represents optionally substituted alkanediyl, alkenediyl, aza alkendiyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene,
A ^{2 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -N (A ⁴ ) -, wherein A ^{4 represents} hydrogen, hydroxy, alkyl , Alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
A ² furthermore represents optionally substituted alkanediyl, alkenediyl, aza alkendiyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene,
A ³ for hydrogen (with the proviso that A ¹ and A ² do not equally represent single bonds), hydroxy, amino, cyano, isocyano, thio cyanato, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, each optionally substituted Alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl, for in each case optionally substituted alkenyl, alkenyloxy, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxybenzene, for substituted alkylphenyls, in each case for substituted alkylphenyl , Cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, or represents in each case optionally substituted aryl or heterocyclyl,
however, in each individual case A ¹ and A ² do not equally represent one of the radicals O, S, -SO- or -SO ₂ -,
X ^{1 represents} hydrogen, halogen or optionally substituted alkyl,
X ^{2 represents} haloalkyl, and
X ^{3 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl or alkoxycarbonyl.

In the definitions are the hydrocarbon chains, such as alkyl or alkanediyl - Also in conjunction with heteroatoms, such as in alkoxy - each straight-chain or branched.

Preferred substituents or preferred ranges of the radicals present above and below on formulas are defined below.
R ² preferably represents cyano, carbamoyl, thiocarbamoyl, halogen, alkyl or alkoxy each optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, each having 1 to 10 carbon atoms, or optionally nitro, cyano, halogen, C. ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy substituted arylalkoxy having 6 or 10 carbon atoms in the aryl group and 1 to 4 carbon atoms in the alkyl part.
R ³ preferably represents the group -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 -N (A ⁴ ) -, in which A ^{4 represents} hydrogen, hydroxy, or for in each case optionally substituted by halogen substituted C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, phenyl or phenylsulfonyl,
A ¹ furthermore for C ₁ -C ₆ -alkanediyl which is optionally substituted by halogen (in particular fluorine and / or chlorine), C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ -azaalkenediyl, C ₂ -C ₆ -alkindiyl, C ₃ -C ₆ -cycloalkanediyl, C ₃ - C ₆ is cycloalkenediyl or phenylene,
A ^{2 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -N (A 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 for C ₁ -C ₆ -alkanediyl which is optionally substituted by halogen (in particular fluorine and / or chlorine), C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ -azaalkenediyl, C ₂ -C ₆ -alkindiyl, C ₃ -C ₆ -cycloalkanediyl, C ₃ - C ₆ is cycloalkenediyl or phenylene,
A ³ for hydrogen (with the proviso that A ¹ and A ² do not equally represent single bonds), hydroxy, amino, cyano, isocyano, thiocyanato, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for in each case optionally substituted by fluorine, chlorine or C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkyl, C ₁ - C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfmyl, C ₁ - C ₆ alkyl sulfonyl, C ₁ -C ₆ alkylamino, di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₆ alkoxy carbonyl or di (C ₁ -C ₆ alkoxy) - ( thio) phosphoryl, for each optionally substituted by cyano, fluorine and / or chlorine and / or C ₁ -C ₄ alkoxycarbonyl-substituted C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkenyloxy or C ₂ -C ₆ alkenylamino, C ₂ -C ₆ -Alkylidenamino or C ₂ -C ₆ - alkenyloxy-carbonyl, or represents optionally cyano-, fluorine and / or chlorine and / or C ₁ -C ₄ -alkoxy-carbonyl-substituted C ₂ -C ₆ -Alkynyl, C ₂ -C ₆ -alkynyloxy or C ₂ -C ₆ -alkynylamino, for C ₂ -C ₆ -alkynyloxy approx rbonyl, represents in each case optionally fluorine, chlorine, cyano, carb oxy, 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 cycloalkylideneamino, C ₃ -C ₆ cycloalkyloxycarbonyl or C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkoxy-car bonyl, 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 aryl with 6 or 10 carbon atoms or heterocyclyl with 1 to 5 carbon atoms, 1 to 4 nitrogen atoms and / or 1 of the 2 oxygen or sulfur atoms,
however, A ¹ and A ² in each individual case do not equally represent one of the radicals O, S, -SO- or -SO ₂ -.
X ¹ preferably represents hydrogen, halogen or alkyl having 1 to 10 carbon atoms which is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy.
X ² preferably represents haloalkyl having 1 to 10 carbon atoms.
X ³ preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarb amoyl, halogen, or alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 10 carbon atoms.
R ¹ particularly preferably represents fluorine or chlorine;
R ² particularly preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, and in each case methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy; n-, 1-, s- or t-butyl., n-, i-, s-, t- or neo-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or for each optionally by nitro, cyano, fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichlor methyl or chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, fluorodichloromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoro Trifluoroethoxy, trichloroethoxy, chlorodifluoroethoxy or fluorodichloroethoxy substituted phenylmethoxy, phenylethoxy or phenylpropoxy.
R ³ particularly preferably 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 -N (A ⁴ ) -, wherein A ^{4 represents} hydrogen, hydroxy, or for each optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, propenyl, butenyl, propynyl, butynyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio , n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfmyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, phenyl or phenylsulfonyl,
also 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- is diyl, propene-1,2-diyl or propene-1,3-diyl,
A ^{2 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -N (A 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 (with the proviso that A ¹ and A ^{2 then} do not equally represent single bonds), hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, each optionally with fluorine, chlorine , Methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, 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-propoxycarbonyl, for ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, which is optionally substituted by fluorine and / or chlorine, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Propeny lamino or butenylamino, for propylidenamino, butylidenamino, propenyloxycarbonyl or butenyloxycarbonyl, for each optionally substituted by fluorine and / or chlorine, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, substituted ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino , for propynyloxycarbonyl or butynyloxycarbonyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentyl methyl, Cyclohexylmethyl, Cyclopropylmethoxy, Cyclobutylmeth oxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopentylidenamino, Cyclohexylidenamino, Cyclopentyloxycarbonyl, Cyclohexyl oxycarbonyl, Cyclopentylmethoxycarbonoxy, Cyclo, Nitro, for Nitrogen, for Carbonyl, Cyclo, or Nitro for Carbonano, Cyclo, or Nitro for Carbonyl, Cyclo, or Nitro for Carbonyl, Cyclo, or Nitro for Carbonyl boxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl-substituted phenyl, furyl, thienyl, Pyrrolyl, pyrazolyl, imidazolyl, oxiranyl, oxetanyl, dioxolanyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl or pyrimidinyl,
however, A ¹ and A ^{2 are} not both each one of the radicals O, S, -SO- or -SO ₂ -.
X ¹ particularly preferably represents hydrogen, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, which is in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butyl.
X ² particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each substituted by fluorine and / or chlorine.
X ³ particularly preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl, eth oxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl.
R ² very particularly preferably represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, and methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, each optionally substituted by fluorine, chlorine, methoxy or ethoxy , or for optionally by nitro, cyano, fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl or chlorodifluoromethyl, methoxy , Ethoxy, n- or i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy or trifluoroethoxy substituted phenylmethoxy.
R ³ very particularly preferably represents the group -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 N (A ⁴ ) -, where A ^{4 represents} hydrogen, hydroxy, methyl, Ethyl, n- or i-propyl, propenyl, butenyl, propynyl, butinyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t- Butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methyl sulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, phenyl or phenyl sulfonyl,
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, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -N (A ⁴ ) -, wherein A ^{4 represents} hydrogen, methyl, ethyl , n- or i-propyl, methylsulfonyl, ethyl sulfonyl, 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 (with the proviso that A ¹ and A ^{2 then} do not equally represent single bonds), hydroxy, amino, cyano, nitro, carboxy, carbamoyl, fluorine, chlorine, bromine, each optionally with fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, Ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for propenyl, butenyl, propenyloxy, butenyloxy, which are each optionally substituted by fluorine or chlorine, Propenyl amino, butenylamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, or for each case optionally by nitro, cyano, carboxy, fluorine, chlorine, B rom, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, eth oxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxy carbonyl and / or ethoxycarbonyl substituted phenyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl , Oxetanyl, dioxolanyl, pyridinyl or pyrimidinyl,
however, A ¹ and A ^{2 are} not both each one of the radicals O, S, -SO- or -SO ₂ -.
X ¹ very particularly preferably represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.
X ² very particularly preferably represents methyl, ethyl, n- or i-propyl each substituted by fluorine and / or chlorine.
X ³ very particularly preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxycarbonyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Ethoxycarbonyl, n- or i-propoxycarbonyl.

The radicals listed above or listed in preferred areas Definitions apply both to the end products of the formula (I) and accordingly for the starting or intermediate products required for the production. This Residual definitions can be between themselves, that is, between the specified ones areas can be combined as required.

Those compounds of the formula (I) are preferred according to the invention which is a combination of the meanings listed above as preferred is present.

According to the invention, particular preference is given to those compounds of the formula (I) in which a combination of those listed as particularly preferred above Meanings exist.

According to the invention, those compounds of the Formula (I), in which a combination of the above is particularly preferred added preferred meanings is present.

Saturated or unsaturated hydrocarbon residues such as alkyl or alkenyl - also in connection with heteroatoms, such as in alkoxy - as far as possible in each case straight-chain or branched.

Optionally substituted radicals can be mono- or polysubstituted, in the case of multiple substitution, the substituents are the same or different can.

A very particularly preferred group are those compounds of the formula (I) in which
Q stands for O (oxygen),
R ^{1 represents} fluorine or chlorine,
R ^{2 represents} cyano, thiocarbamoyl, fluorine, chlorine or bromine,
R ³ for hydroxy, amino, cyano, nitro, carboxy, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyanomethyl, cyanoethyl, carboxy methyl, carboxyethyl, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, Chlorfluorethyl, trifluoroethyl, trichloroethyl, Fluordichlorethyl, Chlordifluor ethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy carbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxy carbonyl-ethyl, methoxy, ethoxy , n- or i-Propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, di chloroethoxy, chlorofluoroethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethyllethyl, methylthio, fluorothethylthio, methylthio, thio, fluorothethylthio, methylthio, thio, , n- or i-Propyl sulfinyl, Trifluomiethylsulfmyl, Methylsulfonyl, Ethy lsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, propenyl, butenyl, fluoropropenyl, chloropropenyl, dichlorophenyl, difluoropropyl, Fluorbutenyl, Chlorbutenyl, Difluorbutenyl, Dichlorbutenyl, Chlorfluorbutenyl, Trifluorbutenyl, trichloro butenyl, Fluordichlorbutenyl, Chlordifluorbutenyl, propenyloxy, butenyloxy, Fluorpropenyloxy, Chlorpropenyloxy, Difluorpropenyloxy, Dichlorpropenyl oxy, Chlorfluorpropenyloxy, Fluorbutenyloxy, Chlorbutenyloxy, difluoro butenyloxy, Dichlorbutenyloxy, Chlorfluorbutenyloxy, Trifluorbutenyloxy, Trichlorbutenyloxy, Fluordichlorbutenyloxy , Chlorodifluorobutenyloxy, propenylamino, butenylamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl, butynyloxycarbonyl, each by methoxycarbonyl, ethoxycarbonyl, n- or i-pro poxycarbonyl substituted methoxy or ethoxy, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, cyclopropylsulfonylamino, N, N-bis (methylsulfonyl) -amino, N, N-bis - (ethylsulfonyl) amino, N-ethylsulfonyl-N-methylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, N-butyroyl-N-methylsulfonyl-amino, Ni - Butyroyl-N-methylsulfonyl-amino, N-pivaloyl-N-methylsulfonyl-amino, N-ethenylcarbonyl-N-methylsulfonylamino, N- (t-butylthio) -N-methylsulfonylamino, N-cyclopentylcarbonyl-N-methylsulfonylamino, N- Acetyl-N-ethyl sulfonyl-amino, N-propionyl-N-ethylsulfonyl-amino, N-butyroyl-N-ethyl sulfonyl-amino, Ni-butyroyl-N-ethylsulfonyl-amino, N-pivaloyl-N-ethyl sulfonyl-amino , N-ethenylcarbonyl-N-ethylsulfonylamino, N- (t-butylthio) - N-methylsulfonylamino, N-cyclopropylcarbonyl-N-ethylsulfonylamino, N- (4-methoxy-phenylacetyl) -N-methylsulfonylamino, N- (4- Methoxy-phenyl acetyl) -N-ethylsulfonyl-amino, 4- (Me thoxycarbonylmethoxy) phenoxy, 4- (ethoxycarbonylmethoxy) phenoxy, 4- (1-methoxycarbonylethoxy) phenoxy, 4- (1-ethoxycarbonylethoxy) phenoxy, 1-methyl-pyrazol-5-yl-oxy, 1 Ethyl pyrazol-5-yl-oxy, 1,3-dimethyl-pyrazol-5-yl-oxy or pyrimidin-2-yl-oxy,
X ^{1 represents} hydrogen or methyl,
X ^{2 represents} trifluoromethyl, and
X ^{3 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, methoxy carbonyl or ethoxycarbonyl.

The new substituted 1-aryl-pyridin-2- (thi) ones of the general formula (I) have interesting biological properties. They are particularly characterized by strong herbicidal activity.

The new substituted 1-aryl-pyridin-2- (thi) ones of the general formula (I) are obtained if pyridin-2- (thi) ones of the general formula (II)

in which
Q, X ¹ , X ² and X ^{3 have} the meaning given above,
with halogen arenes of the general formula (III)

in which
R ¹ , R ² and R ^{3 have} the meaning given above and
X ^{4 represents} halogen (especially fluorine or chlorine),
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and optionally using the compounds of the general formula (I) thus obtained to carry out further conversion reactions (“subsequent reactions”) as part of the substituent definition by customary methods.

Subsequent reactions are preferably substitution reactions (e.g. R ² : Br → CN, R ³ : F → OCH ₃ , NH-SO ₂ -CH ₃ ) and oxidation reactions (e.g. R3: SCH ₃ → SO ₂ CH ₃ ) , as well as addition reactions (z. B. R ² CN → CSNH ₂ ) called (see the manufacturing examples).

If, for example, 5-methyl-4-trifluoromethyl-2 (1H) -pyridinone and 2,4,5-trifluorobenzonitrile are used as starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the pyridin-2- (thi) ones to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (II), Q, X ¹ , X ² and X ³ preferably or in particular have those meanings which, in connection with the description of the compounds of the general formula (I) according to the invention, are preferred or particularly preferred for Q, X ¹ , X ² and X ^{3 have been} given.

The starting materials of the general formula (II) are known and / or can be according to known processes can be prepared (cf. J. Fluorine Chem. 93 (1999), 153-157; EP-A-216541, EP-A-259048, EP-A-398499, EP-A-488220, US-A- 3754088, US-A-4156734).

The pyridin-2- (thi) ones of the general formula (II) are obtained if (α) aminopyridines of the general formula (IV)

in which
X ¹ , X ² and X ^{3 have} the meaning given above,
with diazotizing agents, such as. B. sodium nitrite and aqueous sulfuric acid at temperatures between -10 ° C and + 10 ° C and after heating to temperatures between 40 ° C and 100 ° C with an alkali metal or alkaline earth metal compound, such as. B. sodium or potassium hydroxide or sodium or potassium carbonate at a pH between 6 and 9 (see. The manufacturing examples)
or if you
(β) halopyridines of the general formula (V)

in which
X ¹ , X ² and X ^{3 have} the meaning given above and
X ^{5 represents} halogen (especially fluorine or chlorine)
with alkali metal or alkaline earth metal hydroxides, such as. As sodium or potassium hydroxide, in the presence of diluents, such as. B. tert-butanol at temperatures between 20 ° C and 120 ° C (see. The manufacturing examples).

The precursors of formulas (IV) and (V) are known and / or can according to known processes can be prepared (cf. J. Fluorine Chem. 21 (1982), 265-286; 10c. cit. 93: 153-157 (1999); US-A-4699983, US-A-4725607, US-A-4775762; Preparation Examples).

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

The starting materials of the general formula (III) are known and / or can be according to processes known per se (cf. EP-A-191181, EP-A-370332, EP-A-431373, EP-A-441004, EP-A-597360).

The process according to the invention for the preparation of compounds of general Formula (I) is preferably carried out using a reaction aid guided. As reaction aids for the inventive method come in generally the usual inorganic or organic bases or Acid Accept gates into consideration. These preferably include alkali metal or alkaline earth metal, acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, Sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, Sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, s or t butoxide; also basic organic nitrogen compounds, such as such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropyl amine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4- Methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5- Ethyl-2-methyl-pyridiu, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diaza bicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1.8 Diazabicyclo [5.4.0] -undec-7-ene (DBU).

The process according to the invention for the preparation of the compounds of general Formula (I) is preferably carried out using a diluent leads. As a diluent for carrying out the method according to the invention inert organic solvents are particularly suitable. This includes ins special aliphatic, alicyclic or aromatic, optionally halogenated Hydrocarbons, such as gasoline, benzene, toluene, xylene, chlorobenzene, Dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetra  chlorine-carbon; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or Methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; Esters such as acetic acid methyl ester or ethyl acetate, sulfoxides, such as dimethyl sulfoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether or diethylene glycol monoethyl.

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 Reaction is generally carried out in a suitable diluent were carried out a reaction auxiliary and the reaction mixture is in space agitated several hours at the required temperature. The on work is carried out according to customary methods (cf. games).

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. ver used in the following plants:
Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Gupopsisia, Euphorbia , Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsesb, Senania, Senecio , Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaiia, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostiseterististochocho, Eriocha , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.

However, 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 used 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 compounds according to the invention can be used in certain concentrations or Application rates also to control animal pests and fungal or bacterial plant diseases can be used. You let yourself be optionally also as intermediates or precursors for the synthesis of others Use active ingredients.

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including naturally occurring crops). Cultivated plants can be plants that by conventional breeding and optimization methods or by organic technological and genetic engineering methods or combinations of these  Methods can be obtained, including transgenic plants and one finally, those that can be protected or not protected by plant variety rights Plant varieties. Under plant parts, all above-ground and underground Parts and organs of plants, such as shoot, leaf, flower and root understood with leaves, needles, stems, stems, flowers, fruiting bodies, Fruits and seeds as well as roots, tubers and rhizomes are listed. To the Plant parts also include crops, vegetative and generative ver propagation material, for example cuttings, tubers, rhizomes, offshoots and Seeds.

The treatment of plants and parts of plants according to the invention with the Active substances take place directly or by influencing their environment, living space or storage room according to the usual treatment methods, e.g. B. by diving, Spraying, vaporizing, atomizing, scattering, spreading and when propagating material, especially in the case of seeds, continues with one or more layers Envelop.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient im impregnated natural and synthetic materials as well as very fine encapsulation in polymers Substances.

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

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 stone powder; how finely dispersed Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, Coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foam Generating funds are possible: z. B. non-ionic and anionic emuls gators, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants come into question: z. B. lignin sulfite and Methylcellulose.

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. Further 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 in a mixture with known herbicides and / or with substances which Improve crop tolerance ("safeners") for weed control ver be applied; ready formulations or tank mixes are possible. It So mixtures with weed control agents are also possible, which a or contain several known herbicides and a safener.

Known herbicides are suitable for the mixtures, for example Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Benfuresate, Bensulf uron (-methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxime, Bromoxynil, Butachlor, Butafenacil (-allyl), Butroxydim, Butylate, Cafenstrole, Caloxydim, carbetamides, carfentrazone (-ethyl), chloromethoxyfen, chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cini don (-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Clor ansulam (methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichloroprop (-P), dicloföp (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, Diflufenican, Diflufenzc <pyr, Dimefuron, Dimepiperate, Dimethachlor, Dimetha metryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop (-P-  ethyl), fentrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufenacet, Flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, fluometuron, Fluorochloridones, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl), Flurprimidol, hlurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Foramsulirone, glufosinate (-ammonium), glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl, -P-methyl), Hexazinone, Imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, Imazosulfuron, iodosulftiron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Lin uron, MCPA, mecoprop, mefenacet, mesotrione, metamitron, metazachlor, metha benzthiazuron, metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Napro anilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, Oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, Pelargonic acid, Pendimethalin, Pendralin, Pentoxazone, Phenmedipham, Picolinafen, Piperophos, Pretilachlor, Primisulfuron (-methyl), Profluazol, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzamide, Prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolates, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol, pyriftalid, Pyriminobac (methyl), pyrithiobac (sodium), quinchlorac, quinmerac, quin oclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron, sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulf uron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, Thiafluamides, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thiobencarb, Tio carbazil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), triclopyr, tri diphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron.  

Also a mixture with other known active ingredients, such as fungicides, insects ticides, acaricides, nematicides, bird repellants, plant nutrients substances 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 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 start out the following examples.  

Preparation Examples

example 1

13 g (80 mmol) of 4-trifluoromethyl-pyridin-2 (1H) -one are dissolved in 90 ml of dimethyl sulfoxide with 11.5 g (84 mmol) of potassium carbonate and 12.6 g (80 mmol) of 2,4,5-trifluoro benzonitrile stirred for 90 minutes at 40 ° C, then mixed with 300 ml of water, with conc. Acidified hydrochloric acid, precipitated product isolated by filtration, with Washed water and dried. For cleaning, cyclohexane with 10% Isopropanol recrystallized.

11.2 g (47% of theory) of 1- (4-cyano-2,5-difluorophenyl) -4-trifluoromethyl-2 (1H) -pyridone of melting point 131 ° C. are obtained.
Log P (pH2): 2.30.

Example 2

(Subsequent reaction)

3.6 g (12 mmol) of 1- (4-cyano-2,5-difluorophenyl) -4-trifluoromethyl-2 (1H) pyridone are in 100 ml of dimethyl sulfoxide with 3.3 g (24 mmol) of potassium carbonate and 1.47 g (13.5 mmol) Ethanesulfonsäureamid stirred at 120 ° C for 4 hours. The mixture is concentrated under reduced pressure, the residue is stirred with water, with conc. Acidified hydrochloric acid, precipitated product isolated by filtration, with Washed water and dried.

4.45 g (95% of theory) of 1- (4-cyano-5-ethylsulfonylamino-2-fluorophenyl) -4-trifluoromethyl-2 (1H) -pyridone of melting point 75 ° C. are obtained.
Log P (pH 2): 2.07

Example 3

(Subsequent reaction)

1.5 g (4.8 mmol) of 1- (4-cyano-2,5-difluorophenyl) -4-trifluoromethyl-5-methyl-2 (1H) - pyridone are placed in 50 ml of acetonitrile with 0.7 g (9.6 mmol) of 3-butyn-2-ol, at Room temperature (approx. 20 ° C) in portions with 0.24 g (9.6 mmol) sodium hydride (95% in paraffin) and stirred for 12 hours at room temperature. The Mixture is concentrated under reduced pressure, the residue is mixed with water stirs, with conc. Hydrochloric acid adjusted to pH 5 and the precipitated product through Filtration isolated.  

1.4 g (82% of theory) of 1- [5- (but-1-yn-3-yl-oxy) -4-cyano-2-fluorophenyl] -4-trifluoromethyl-5-methyl-2 are obtained (1H) pyridone, melting point 169 ° C.
Log P (PH 2): 3.01.

Example 4

(Subsequent reaction)

0.13 g (3.25 mmol) sodium hydride (60%) are at room temperature (approx. 20 ° C) to a solution of 0.95 g (2.32 mmol) of 1- (4-cyano-5-ethylsulfonylamino-2-fluorine phenyl) -4-trifluoromethyl-2 (1H) -pyridone in 10 ml of tetrahydrofuran and the Mixture is stirred for 20 minutes at room temperature. In parallel, 0.23 g (1.29 mmol) bis-butyl disulfide in 10 ml tetrahydrofuran at -30 ° C with 0.185 g (1.37 mmol) sulfuryl chloride are added and the mixture is kept at -30 ° C. for 30 minutes stirred to -35 ° C. The two mixtures are combined and 150 without cooling Minutes stirred. Then water is carefully added and then with aqueous 1 N hydrochloric acid / ethyl acetate shaken. The organic phase will separated, dried with sodium sulfate and filtered. The filtrate is under ver reduced pressure and the residue (1.3 g of crude product) column chromato graphically processed.

0.50 g (43% of theory) of 1- [4-cyano-5- (N-ethylsulfonyl-Nt-butylthioamino) -2-fluorophenyl] -4-trifluoromethyl-2 (1H) -pyridone are obtained as oily product.
Log P (pH 2): 3.31.

Analogously to Examples 1 to 4 and in accordance with the general description of the production process according to the invention, the compounds of the general formula (I) listed in Table 1 below can also be prepared, for example.

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Table 1

Examples of the compounds of the formula (I)

Starting materials of formula (II)

Example (II-1)

step 1

24.5 g (135 mmol) of 2-chloro-4-trifluoromethyl-pyridine are concentrated in 400 ml. aqueous ammonia stirred for 24 hours at 170 ° C in an autoclave. After the Ent tension is extracted with ethyl acetate, the organic phase with water washed, dried over sodium sulfate and carefully under reduced pressure concentrated. 18.5 g (85% of theory) of 2-amino-4-trifluoromethyl-pyridine are obtained melting point 72 ° C.

Level 2

10 g (61.7 mmol) of 2-amino-4-trifluoromethyl-pyridine are mixed into a mixture 150 ml of 10% sulfuric acid and 100 g of ice are added and at 0 ° C to 5 ° C then a solution of 4.3 g (61.7 mmol) of sodium nitrite in 50 ml of water within added dropwise of 30 minutes. The mixture is then heated to 70 ° C., one Stirred at 70 ° C for hours, adjusted to pH 7 with sodium carbonate and the solution concentrated to 100 ml volume under reduced pressure. The fancy Solid is isolated by filtration and washed with water. 6.2 g are obtained (62% of theory) 4-trifluoromethyl-pyridin-2 (1H) -one with a melting point of 161 ° C.  

Example (II-2)

step 1

216 g of 4-methyl-pyridin-2-amine are hydrogenated at -5 ° C to + 5 ° C in 800 ml fluoride entered in portions and the mixture is 3 hours at 0 ° C to + 5 ° C stirred. Then 152 g of sodium nitrite are added in portions, the Re Action mixture come to room temperature (approx. 20 ° C) and finally warms up to 70 ° C until gas evolution has ceased. Then you pour the Re action mixture on ice, adjusts to pH by adding potassium hydroxide Value between 8 and 9 and extracted with methylene chloride. The organic phase is by distillation, first under atmospheric pressure, then under ver worked up under reduced pressure. 155 g (70% of theory) of 2-fluoro-4- are obtained. methyl-pyridine with a boiling range of 84 ° C to 86 ° C (at 101 mbar).

Level 2

323 g of 2-fluoro-4-methyl-pyridine are placed in 1950 ml of carbon tetrachloride and 348 g of chlorine are introduced at 80 ° C. in the course of 5 hours. In others A total of 1059 g of chlorine are introduced at reflux temperature for 5 days. Then the carbon tetrachloride is distilled off and the residue in 1000 ml of 4-chlorine benzotrifluoride added. Then within 3 days at 110 ° C  600 g of chlorine introduced. After nitrogen has been passed through, distillation worked up under reduced pressure. 412 g of 2-fluoro-4-trichloromethyl are obtained pyridine with a boiling range of 103 ° C to 107 ° C (at 29 mbar). Refractive index n 20 | D 1.5303.

level 3

A mixture of 33 g of 2-fluoro-4-trichloromethylpyridine, 35 g of antimony (III) fluoride and 3 ml of antimony (V) chloride is heated to 140 ° C to 142 ° C for one hour and then worked up by distillation. 20 g of a product mixture are obtained contains 60.3% of 2-fluoro-4-trifluoromethyl-pyridine according to gas chromatographic analysis.

Level 4

25 g (151 mmol) of 2-fluoro-4-trifluoromethyl-pyridine are tert in 200 ml. butanol submitted with 16.3 g (290 mmol) of potassium hydroxide and 3 hours on return flow temperature stirred. The solution is concentrated under reduced pressure Residue mixed with water, with conc. Acidified hydrochloric acid and with acetic acid extracted ethyl ester. The organic phase is dried over sodium sulfate and filtered. The filtrate is carefully concentrated under reduced pressure. You get 13 g (53% of theory) of 4-trifluoromethyl-pyridin-2 (1H) -one from the melting point 160 ° C.

The production route according to example (II-2) for the compounds of formula (II) is not yet known from the literature and as such is also the subject of the lying registration.  

Example (II-3)

2.45 g (15 mmol) of 4-trifluoromethyl-pyridin-2 (1H) -one are dissolved in 20 ml of trichlor submitted methane and mixed with 2.02 g (15 mmol) of N-chlorosuccinimide. The Mixture is stirred at reflux temperature for 4 hours and then with ver reduced pressure. The residue is stirred with water and poured out falling product isolated by filtration. The crude product is column chromato graphically (silica gel, eluent: 1. toluene / ethyl acetate to separate the Contamination, 2. methanol for product isolation) cleaned. 1.1 g are obtained (37% of theory) 5-chloro-4-trifluoromethyl-pyridin-2 (1H) -one from the melting point 171 ° C.  

applications Example A Pre-emergence test

Solvent: 5 parts by weight of acetone
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 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 drug concentration in the spray liquor is chosen so that the ge in 1000 liters of water per hectare desired 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 the preparation example show 1, 2, 3, 5, 6 and 7 with good tolerance to crops, such as z. B. Soy and wheat, strong action against weeds.  

Example B Post-emergence test

Solvent: 5 parts by weight of acetone
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.

Test plants with a height of 5 are sprayed with the active ingredient preparation -15 cm 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 the preparation example show 1, 2, 3, 5, 6 and 7 with good tolerance to crops, such as z. B. wheat, strong action against weeds.

Claims (8)

1. Compounds of the general formula (I)
in which
Q represents O (oxygen) or S (sulfur),
R ^{1 represents} halogen,
R ^{2 represents} cyano, carbamoyl, thiocarbamoyl, halogen, or represents optionally substituted alkyl, alkoxy or arylalkoxy,
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 -N (A ⁴ ) -, wherein A ^{4 represents} hydrogen, hydroxy, or represents in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, aryl or arylsulfonyl,
A ¹ furthermore represents optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene,
A ^{2 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping N (A ⁴ ) -, in which
A ^{4 represents} hydrogen, hydroxy, alkyl, alkoxy, aryl, alkyl sulfonyl or arylsulfonyl,
A ² furthermore represents optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene,
A ³ for hydrogen (with the proviso that A ¹ and A ^{2 then} do not equally represent single bonds), hydroxy, arnino, cyano, isocyano, thiocyanato, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for each optionally substituted Alkyl, alkoxy, alkylthio, alkyl sulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxy carbonyl or dialkoxy (thio) phosphoryl, for optionally substituted alkenyl, alkenyloxy, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbon optionally substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, or represents in each case optionally substituted aryl or heterocyclyl,
however, in each individual case A ¹ and A ² do not equally represent one of the radicals O, S, -SO- or -SO ₂ -,
X ^{1 represents} hydrogen, halogen or optionally substituted alkyl,
X ^{2 represents} haloalkyl, and
X ^{3 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl or alkoxycarbonyl. 2. Compounds according to claim 1, characterized in that
R ² for cyano, carbamoyl, thiocarbamoyl, halogen, for alkyl or alkoxy each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having 1 to 10 carbon atoms, or for optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy substituted arylalkoxy having 6 or 10 carbon atoms in the aryl group and 1 to 4 carbon atoms in the alkyl part,
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 -N (A ⁴ ) -, wherein A ^{4 represents} hydrogen, hydroxy, or for in each case optionally substituted by halogen C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ - C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C _6- alkyl sulfinyl, C ₁ -C ₆ -alkylsulfonyl, phenyl or phenylsulfonyl,
A ² further for C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ -azaalkenediyl, C ₂ -C ₆ -alkindiyl, each optionally substituted by halogen (in particular special fluorine and / or chlorine), C ₃ -C ₆ cycloalkanediyl, C ₃ -C ₆ cycloalkenediyl or phenylene,
A ^{2 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -N (A 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 further for C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, Cr-C ₆ -azaalkenediyl, C ₂ -C ₆ -alkindiyl, C ₂ -C ₆ each optionally substituted by halogen (in particular fluorine and / or chlorine) ₃ -C ₆ cycloalkanediyl, C ₃ -C ₆ cycloalkenediyl or phenylene,
A ³ for hydrogen (with the proviso that A ¹ and A ² do not equally represent single bonds), hydroxy, amino, cyano, isocyano, thiocyanato, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for in each case optionally substituted by fluorine, chlorine or C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, 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 -alkoxy-carbonyl or di- (C ₁ - C ₆ -alkoxy) - ( thio) phosphoryl, for in each case optionally substituted by cyano, fluorine and / or chlorine and / or C ₁ -C ₄ alkoxycarbonyl, substituted C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkenyloxy or C ₂ -C ₆ - alkenylamino, C ₂ -C ₆ -Alkylidenamino or C ₂ -C ₆ -alkenyl oxy-carbonyl, or represents optionally cyano-, fluorine and / or chlorine and / or C ₁ -C ₄ -alkoxy-carbonyl-substituted C ₂ -C ₆ - Alkynyl, C ₂ -C ₆ -alkynyloxy or C ₂ -C ₆ -alkynylamino, for C ₂ - C ₆ -alkynyloxyca rbonyl, for in each case optionally substituted by fluorine, chlorine, cyano, carboxy, C ₁ -C ₄ -alkyl and / or C ₁ -C ₄ -alkoxycarbonyl-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 cyclo alkyl-C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkylideneamino, 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 -Ca alkyl, C ₁ -C ₄ halo alkyl , C ₁ -C ₄ alkyloxy, C ₁ -C ₄ haloalkyloxy and / or C ₁ - C ₄ alkoxy-carbonyl substituted aryl having 6 or 10 carbon atoms or heterocyclyl having 1 to 5 carbon atoms, 1 to 4 nitrogen atoms and / or 1 of the 2 oxygen or sulfur atoms,
however, in each individual case A ¹ and A ² do not equally represent one of the radicals O, S, -SO- or -SO ₂ -,
X ^{1 represents} hydrogen, halogen or alkyl having 1 to 10 carbon atoms which is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy,
X ^{2 is} haloalkyl having 1 to 10 carbon atoms, and
X ^{3 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or fir alkyl or alkoxy carbonyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 10 carbon atoms. 3. Compounds according to claim 1, characterized in that
R ^{1 represents} fluorine or chlorine,
R ² for cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butyl, n-, i-, s-, t- or neo-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or for each optionally by nitro, cyano, fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl or chlorodifluoromethyl, Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, fluoromethoxy, di fluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluorethoxy, trifluoroethoxy, trichloro Chlorodifluoroethoxy or fluorodichloroethoxy substituted phenylmethoxy, phenylethoxy or phenylpropoxy,
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 -N (A ⁴ ) -, in which
A ⁴ for hydrogen, hydroxyl, or for methyl, ethyl, n- or i-propyl, propenyl, butenyl, propynyl, butinyl, methoxy, ethoxy, n- or i-propoxy, methylthio, each optionally substituted by fluorine and / or chlorine, Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethyl sulfmyl, n- or i-propylsulfinyl, methylsulfonyl, ethyl sulfonyl, n- or i-propylsulfonyl, phenyl or phenylsulfonyl .
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- is diyl, propene-1,2-diyl or propene-1,3-diyl,
A ^{2 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -N (A 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 (with the proviso that A ¹ and A ^{2 then} do not equally represent single bonds), hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, each optionally with fluorine, chlorine , Methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, 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, ethylsulfmyl, 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-propoxycarbonyl, for in each case optionally substituted by fluorine and / or chlorine, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, ethenyl, propenyl, butenyl, propenyl oxy, butenyloxy, propenylam ino or butenylamino, for propylidenamino, butylidenamino, propenyloxycarbonyl or butenyloxycarbonyl, for each optionally substituted by fluorine and / or chlorine, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, substituted ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino , for propynyloxycarbonyl or butynyloxycarbonyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclo pentylmethyl, Cyclohexylmethyl, Cyclopropylmethoxy, Cyclobutylmethoxy, Cyclopentylmethoxy, Cyclohexylmeth oxy, Cyclopentylidenamino, Cyclohexylidenamino, Cyclo penTyloxycarbonyl, Cyclohexyloxycarbonyl, Cyclopentyl methoxycarbonyl, cyclopentyl methoxy methoxy carbonyl, cyclo or cyclo throughyl methoxy carbonyl, cyclo or cyclo throughyl methoxy carbonyl, cyclo or cyclo throughyl methoxy carbonyl, for carbonyl or oxycarboxy, by cyclo or carbonyl by cyclo, or y, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, furyl, thienyl, pyrrolyl , Pyrazolyl, imidazolyl, oxiranyl, oxetanyl, dioxolanyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl or pyrimidinyl,
however, A ¹ and A ² do not both simultaneously represent one of the radicals O, S, -SO- or -SO ₂ -,
X ¹ for hydrogen, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, n-, i- which is optionally substituted by cyano, fluorine, chlorine, methoxy, n- or i-propoxy , s- or t-butyl,
X ² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each substituted by fluorine and / or chlorine, and
X ³ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each methyl, ethyl, n- or i-substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy -Propyl, n-, i-, s- or t-butvl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, n-, i-, s- or t-butoxycarbony1. 4. Compounds according to claim 1, characterized in that
R ^{1 represents} fluorine or chlorine,
R ² for cyano, thiocarbamoyl, fluorine, chlorine, bromine, for in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, or for optionally by nitro, cyano, fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl or chlorodifluoromethyl, methoxy, ethoxy , n- or i-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy or trifluoroethoxy substituted phenylmethoxy,
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 -N (A ⁴ ) -, wherein A ^{4 represents} hydrogen, hydroxy, methyl , Ethyl, n- or i-propyl, propenyl, butenyl, propynyl, butinyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio; n- or i = propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, phenyl 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, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping N (A ⁴ ) -, where A ^{4 represents} hydrogen, methyl, ethyl, n- or i-propyl, methyl sulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenyl sulfonyl,
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 (with the proviso that A ¹ and A ^{2 then} do not equally represent single bonds), hydroxy, araino, cyano, nitro, carboxy, carbamoyl, fluorine, chlorine, bromine, each optionally by fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n or i-propylthio, methylsulfinyl, ethylsulfmyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for propenyl, butenyl, propenyloxy, butenyloxy, optionally substituted by fluorine or chlorine, and propenylamino , Butenylamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine , Methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxetanyl, dioxolanyl , Pyridinyl or pyrimidinyl,
however, A ¹ and A ² do not both simultaneously represent one of the radicals O, S, -SO- or -SO ₂ -,
X ^{1 represents} hydrogen, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
X ² represents methyl, ethyl, n- or i-propyl each substituted by fluorine and / or chlorine, and
X ^{3 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxy carbonyl, which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, is n- or i-propoxycarbonyl. 5. A method for producing the compounds according to claim 1, characterized in that
1-aryl-pyridin-2- (thi) one of the general formula (I), if pyridin-2- (thi) one of the general formula (II)
in which
Q, X ¹ , X ² and X ^{3 have} the meaning given in claim 1,
with halogen arenes of the general formula (III)
in which
R ¹ , R ² and R ^{3 have} the meaning given in claim 1 and
X ^{4 represents} halogen,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and optionally further with the compounds of general formula (I) thus obtained; Conversion reactions in the context of the definition of substituents are carried out according to customary methods. 6. A method for controlling unwanted vegetation, thereby characterized in that at least one compound according to one of the Claims 1 to 4 on undesirable plants and / or their habitat can act. 7. Use of at least one compound according to one of the claims 1 to 4 for controlling unwanted plants. 8. Herbicidal agent, characterized by a content of a compound according to one of claims 1 to 4 and conventional extenders and / or surfactants.