DE19601626A1 - Substituted N-aryl nitrogen heterocycles - Google Patents

Abstract

The invention concerns novel substituted N-aryl nitrogen heterocyclic compounds of general formula (I) in which R<1>, R<2>, Q<1>, Q<2> and Ar have the meanings given in the description. The invention further concerns a process for their preparation and their use as plant-treatment agents, in particular as herbicides and insecticides.

Description

The invention relates to new substituted N-aryl nitrogen heterocycles, processes for their production and their use as plant treatment agents, ins special as herbicides and insecticides.

It is known that certain N-aryl nitrogen heterocycles are herbicidal have shafts (cf. EP 11693, DE 29 52 685, DE 30 26 739, US 4276420, US 4326878, WO 94/14817). The known from the specified patent applications However, connections have not gained any significant significance.

The new substituted N-aryl nitrogen heterocycles of the gen found my formula (I)

in which
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R1 for cyano, formyl, for alkyl optionally substituted by halogen, cyano, carboxy, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkoxycarbonyl, alkenyloxycarbonyl or alkynyloxycarbonyl, for each optionally substituted by halogen alkenyl or alkynyl, each optionally optionally by Halogen-substituted alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl or alkylsulfonyl, or represents cycloalkyl or cycloalkylcarbonyl optionally substituted by halogen, cyano or carboxy,
R² for amino, cyano, formyl, for each optionally substituted by halogen, cyano, carboxy, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkoxycarbonyl, alkenyloxycarbonyl or alkynyloxycarbonyl, alkyl, alkylamino or dialkylamino, each optionally substituted by halogen Alkenyl or alkynyl, in each case optionally substituted by halogen substituted alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl or alkylsulfonyl, or for cycloalkyl or cycloalkylcarbonyl optionally substituted by halogen, cyano or carboxy, and
Ar represents the substituted, monocyclic or bicyclic aryl or heteroaryl group defined below,

wherein
R³ represents hydrogen or halogen,
R⁴ represents hydrogen or halogen,
R⁵ stands for cyano, carboxy, chlorocarbonyl, carbamoyl, thiocarbamoyl, hydroxy, halogen or for alkyl, alkoxy or alkoxycarbonyl optionally substituted by halogen,
R⁶ represents the grouping below,

-A¹-A²-A³

in which
A¹ represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ represents hydrogen, hydroxy, alkyl, alkenyl, alkynyl, alkoxy, aryl, alkylcarbonyl, Arylcarbonyl, alkyl sulfonyl or arylsulfonyl,
A¹ furthermore represents alkane diyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene, each optionally substituted by halogen,
A² represents a single bond, represents oxygen, sulfur, -SO-, SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ represents hydrogen, hydroxy, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
A² furthermore represents alkane diyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene, each optionally substituted by halogen,
A³ represents hydrogen with the proviso that in this case A¹ and / or A² do not represent a single bond
A³ furthermore for hydroxyl, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, each optionally substituted by halogen or alkoxy , Alkoxycarbonyl or dialkoxy (thio) phosphoryl, for alkenyl, alkenyloxy, alkenylthio, alkenyl amino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynyl thio, alkynylamino or alkynyloxycarbonyl, each optionally 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 optionally substituted by nitro, cyano, carboxy, halogen, alkyl, haloalkyl, alkyloxy, haloalkyloxy and / or alkoxycarbonyl Aryl, aryloxy, aralkyl, arylalkoxy, ary loxycarbonyl or arylalkoxycarbonyl,
Farther
A³ for in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thia diazolyl, pyridinyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl Thienylalkyl, oxazolylalkyl, isoxazolylalkyl, thiazolylalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furylalkoxy, represents perhydropyranylalkoxy or pyridylalkoxy, and
R⁷ represents hydrogen or halogen,
or two adjacent residues - R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶ or R⁶ and R⁷ - together represent one of the following groups

-Q³-CQ⁴-, -Q³-CQ⁴-Q⁵-, -Q³-C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -CQ⁴-, -C (R⁸, R⁹) -Q³-CQ⁴-, -Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -, -Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-, -Q³-C (R⁸) = C (R⁸), -C (R⁸) = C (R⁸) -CQ⁴-, -Q³-C (R⁸, R⁹) -CQ⁴-, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-, -C (R⁸) = N-, -Q³-CQ⁴-C (R⁸, R⁹) -, -Q³-CQ⁴-N (R¹⁰) -, -Q³-C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -Q³-CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸) = C (R⁸) -N (R¹⁰) -, -C (R⁸) = C (R⁸) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸) = N-N (R¹⁰) -, -Q³-CQ⁴-C (R⁸, R⁹) -N (R¹⁰) -, Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -

in which
Q³, Q⁴ and Q⁵ are the same or different and each represents oxygen or sulfur,
R⁸ and R⁹ are the same or different and individually represent hydrogen, halogen or alkyl or together represent alkanediyl, and
R¹⁰ for hydrogen, hydroxy, for optionally substituted by cyano, halogen, alkoxy, alkyl-carbonyl or alkoxy-carbonyl-substituted alkyl, alkyl carbonyl, alkoxycarbonyl or alkylsulfonyl, for each optionally substituted by halogen alkenyl or alkynyl, for each given where appropriate by halogen or alkyl substituted cycloalkyl or cycloalkyl alkyl, each represents alkoxy or alkenyloxy optionally substituted by halogen, or arylalkyl or arylalkoxy optionally substituted by cyano, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy.

The new substituted N-aryl nitrogen heterocycles of the general are obtained Formula (I) if one

• (a) (Thio) urazole derivatives of the general formula (II) in which
  Q¹, Q² and Ar have the meanings given above,
  A¹ is hydrogen or has the meanings given above for R¹ and
  A² is hydrogen or has the meanings given above for R²,
  however, at least one of the groups A¹ or A² is hydrogen,
  with alkylating agents of the general formulas (IIIa) or (IIIb) R¹-X (IIIa) R²-X (IIIb) in which
  R¹ and R² have the meanings given above and
  X represents halogen, -O-SO₂-O-R¹ or -O-SO₂-O-R²,
  if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent and if appropriate subsequently carrying out electrophilic or nucleophilic substitution reactions as part of the substituent definition,
  or if you
• (b) (Thio) urazoles of the general formula (IV) in which
  Q¹, Q², R¹ and R² have the meanings given above,
  with halogen arenes of the general formula (V) Ar-X (V) in which
  Ar has the meaning given above and
  X represents halogen,
  if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent and if appropriate subsequently carrying out electrophilic or nucleophilic substitution reactions as part of the substituent definition,
  or if you
• (c) aryl (thio) semicarbazides of the general formula (VI) in which
  Ar, Q¹, R¹ and R² have the meanings given above,
  with (thio) phosgene if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent and if appropriate subsequently carry out electrophilic or nucleophilic substitution reactions as part of the substituent definition in the customary manner.

The compounds of the general formula (I) can also be prepared according to other conventional methods Methods in other compounds of general formula (I) according to the above Definition to be converted, for example by conventional conversions of Carboxylic acid groups or their derivatives (e.g. R⁵: COOH → COCl, COOH → COOCH₃, COCl → CONH₂, COOCH₃ → CONH₂, CONH₂ → CN, CN → CSNH₂), by alkylation reactions (e.g. R¹: H → CH₃ or CHF₂) or by Oxidation or sulfurization (e.g. Q¹: O → S or S → O) - cf. also the her position examples.

The new substituted N-aryl nitrogen heterocycles of the general formula (I) are characterized by strong herbicidal and insecticidal activity.

In the definitions are the saturated or unsaturated hydrocarbon chains such as alkyl, alkenyl or alkynyl each straight or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably Fluorine, chlorine or bromine, especially for fluorine or chlorine.

The invention preferably relates to compounds of the formula (I) in which
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R¹ for cyano, formyl, each optionally by fluorine, chlorine, cyano, carboxy, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy, C₁-C₄-alkylthio, C₃-C₄-alkenylthio, C₃- C₄-alkynylthio, C₁-C₄-alkoxy-carbonyl, C₃-C₄-alkenyloxy-carbonyl or C₃-C₄-alkynyloxy-carbonyl-substituted C₁-C₆-alkyl, for each optionally substituted by fluorine or chlorine-substituted C₃-C₆-alkenyl or C₃ -C₆-alkynyl, for each optionally substituted by fluorine or chlorine, C₁-C₆-alkylcarbonyl, C₃-C₆-alkenyl carbonyl, C₃-C₆-alkynylcarbonyl, C₁-C₆-alkoxy-carbonyl, C₃-C₆-alkenyl oxy -carbonyl, C₃-C₆-alkynyloxy-carbonyl or C₁-C₆-alkylsulfonyl, or for C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-carbonyl optionally substituted by fluorine, chlorine, bromine, cyano or carboxy,
R² for amino, cyano, formyl, for each optionally by fluorine, chlorine, cyano, carboxy, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy, C₁-C₄-alkylthio, C₃-C₄-alkenylthio, C₃-C₄-alkynylthio, C₁-C₄-alkoxy-carbonyl, C₃-C₄-alkenyloxy-carbonyl or C₃-C₄-alkynyloxy-carbonyl-substituted C₁-C₆-alkyl, C₁-C₆-alkylamino or di (C₁-C₄- alkyl) amino, for each optionally substituted by fluorine or chlorine substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, for each optionally substituted by fluorine or chlorine C₁-C₆-alkylcarbonyl, C₃-C₆-alkenylcarbonyl, C₃ -C₆-alkynyl carbonyl, C₁-C₆-alkoxy-carbonyl, C₃-C₆-alkenyloxy-carbonyl, C₃-C₆-alkynyloxy-carbonyl or C₁-C₆-alkylsulfonyl, or for any given case by fluorine, chlorine, bromine, cyano or Carboxy substituted C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-carbonyl, and
Ar represents the substituted, monocyclic or bicyclic aryl or heteroaryl group defined below,

wherein
R³ represents hydrogen, fluorine, chlorine or bromine,
R⁴ represents hydrogen, fluorine, chlorine or bromine,
R⁵ represents cyano, carboxy, chlorocarbonyl, carbamoyl, thiocarbamoyl, hydroxyl, fluorine, chlorine, bromine or alkyl, alkoxy or alkoxy carbonyl, each optionally substituted by fluorine and / or chlorine, each having up to 4 carbon atoms,
R⁶ represents the grouping below,

-A¹-A²-A³

in which
A¹ is a single bond, oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ is hydrogen, hydroxy, C₁-C₄-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl, C₁-C₄-alkoxy, phenyl, C₁-C₄-alkylcarbonyl, phenylcarbonyl, C₁-C₄-alkylsulfonyl or phenylsulfonyl,
A¹ further for each optionally substituted by fluorine, chlorine or bromine, C₁-C Alk-alkanediyl, C₂-C₆-alkenediyl, C₂-C₆-azaalkenedyl, C₂-C₆-alkynediyl, C₃-C₆-cycloalkanediyl, C₃-C₆-cycloalkenediyl or phenylene stands,
A² represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, in which A⁴ represents hydrogen, hydroxy, C₁-C₄-alkyl, C₁-C₄-alkoxy, Phenyl, C₁-C₄ alkylsulfonyl or phenylsulfonyl,
A² further for each optionally substituted by fluorine, chlorine or bromine, C₁-C₆alkanediyl, C₂-C₆alkenediyl, C₂-C₆alkaalkenediyl, C₂-C₆alkanediyl, C₃-C₆cycloalkanediyl, C₃-C₆cycloalkenediyl or phenylene stands,
A³ represents hydrogen, with the proviso that in this case A¹ and / or A² do not represent a single bond,
A³ furthermore for hydroxy, mercapto, amino, cyano, isocyano, thio cyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for alkyl optionally substituted by fluorine, chlorine or C₁-C₄alkoxy , Alkoxy, alkyl thio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alk oxycarbonyl or dialkoxy (thio) phosphoryl each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl optionally substituted by fluorine or chlorine , Alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, each optionally by fluorine, chlorine, cyano, carboxy, C₁-C₄-alkyl and / or C₁-C₄-alkoxy -carbonyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidene amino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each with 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkyloxy, C₁-C₄-haloalkyloxy and / or C₁-C₄-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, phenyloxycarbonyl or phenyl-C₁-C₄-alkoxycarbonyl,
A³ further for each optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, tridylolylidyl, pyridinyl, pyriminyl, pyridinyl, pyridinyl, pyriminyl -C₄-alkyl, furyl-C₁-C₄-alkyl, thienyl-C₁-C₄-alkyl, oxazolyl-C₁-C₄-alkyl, isoxazolyl-C₁-C₄-alkyl, thiazolyl-C₁-C₄-alkyl, pyridinyl-C₁-C₄ -alkyl, pyrimidinyl-C₁-C₄-alkyl, pyrazolyl methoxy, furylmethoxy, represents perhydropyranylmethoxy or pyridyl methoxy, and
R⁷ represents hydrogen, fluorine or chlorine,
or two adjacent residues - R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶ or R⁶ and R⁷ - together represent one of the following groups

-Q³-CQ⁴-, -Q³-CQ⁴-Q⁵-, -Q³-C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -CQ⁴-, -C (R⁸, R⁹) -Q³-CQ⁴-, -Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -, Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-, -Q³-C (R⁸) = C (R⁸) -, -C (R⁸) = C (R⁸) -CQ⁴-, -Q³-C (R⁸, R⁹) -CQ⁴-, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-, -C (R⁸) = N-, -Q³-CQ⁴-C (R⁸, R⁹) -, -Q³-CQ⁴-N (R¹⁰) -, -Q³-C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -Q³-CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸) = C (R⁸) -N (R¹⁰) -, -C (R⁸) = C (R⁸) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸) = N-N (R¹⁰) -, -Q³-CQ⁴-C (R⁸, R⁹) -N (R¹⁰) -, Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -

in which
Q³, Q⁴ and Q⁵ are the same or different and each represents oxygen or sulfur,
R⁸ and R⁹ are the same or different and individually represent hydrogen, fluorine, chlorine, bromine or C₁-C₄-alkyl or together represent C₂-C₅-alkanediyl, and
R¹⁰ for hydrogen, hydroxy, optionally substituted by cyano, fluorine, chlorine, C₁-C₄-alkoxy, C₁-C₄-alkyl-carbonyl or C₁-C₄-alkoxy-carbonyl alkyl, alkylcarbonyl, alk oxycarbonyl or alkylsulfonyl each with 1 to 6 Carbon atoms in the alkyl groups, each for alkenyl or alkynyl optionally substituted by fluorine, chlorine or bromine or alkynyl, each with 2 to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by fluorine, chlorine, bromine or C₁-C₄alkyl, each with 3 to 6 Carbon atoms in the cycloalkyl groups and optionally 1 to 3 atoms in the alkyl group, for alkoxy or alkenyloxy each optionally substituted by fluorine and / or chlorine, each having up to 6 carbon atoms, or for each optionally by cyano, fluorine, chlorine, C₁-C₄ -Alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy substituted benzyl or benzyloxy.

The invention relates in particular to compounds of the formula (I) in which
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R¹ for cyano, formyl, each for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine, chlorine, cyano, carboxy, methoxy or ethoxy, for each optionally by Fluorine or chlorine-substituted propenyl, butenyl, propynyl or butynyl, each represents acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or ethylsulfonyl optionally substituted by fluorine or chlorine, or cyclopropyl optionally substituted by fluorine or chlorine,
R² for amino, cyano, formyl, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylamino, each optionally substituted by fluorine, chlorine, cyano, carboxy, methoxy or ethoxy, Ethylamino, n- or i-propylamino, dimethylamino or diethylamino, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine or chlorine, for acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or ethylsulfonyl, optionally substituted by fluorine or chlorine, or represents cyclopropyl optionally substituted by fluorine or chlorine, and
Ar represents the substituted, monocyclic or bicyclic aryl or heteroaryl group defined below,

wherein
R³ represents hydrogen, fluorine or chlorine,
R⁴ represents hydrogen, fluorine or chlorine or
R⁵ represents cyano, thiocarbamoyl, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy,
R⁶ represents the grouping below,

-A¹-A²-A³

in which
A¹ is a single bond, oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, where A⁴ is hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy , Ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,
A¹ 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 -diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl or propyne-1,3-diyl,
A² represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ represents hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy , Ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A² 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, propene-1,3-diyl, ethyne-1,2-diyl or propyne-1,3-diyl,
A³ represents hydrogen, with the proviso that in this case A¹ and / or A² do not represent a single bond,
A³ furthermore for hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n-, i-, which is optionally substituted by fluorine, chlorine, methoxy or ethoxy -, 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, methyl amino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butyl amino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, di ethoxyphosphoryl or dipropoxyphosphoryl, diisopropoxyphos phoryl, for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycar bonyl, B, in each case optionally substituted by fluorine or chlorine utenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, for each cyclopropyl, cyclobutyl, optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl , Cyclo pentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyl oxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclo pentylmethyl, cyclohexylmethyl, cyclo-propyl methoxy, cyclobutyl methoxy, cyclopentyl methoxy, cyclohexyl methoxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopylyloxy, cyclopoxycarbonyl or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, di fluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or Ethoxy carbonyl substituted phenyl, phenyloxy, benzyl, phenylet hyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl,
A³ furthermore for fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, furylmethyl Thiazolylmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furyl methoxy or pyridylmethoxy,
R⁷ represents hydrogen, fluorine or chlorine,
or two adjacent residues - R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶ or R⁶ and R⁷ - together represent one of the following groups

-Q³-CQ⁴-, -Q³-CQ⁴-Q⁵-, -Q³-C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -CQ⁴-, -C (R⁸, R⁹) -Q³-CQ⁴-, -Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -, -Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-, -Q³-C (R⁸) = C (R⁸) -, -C (R⁸) = C (R⁸) -CQ⁴-, -Q³-C (R⁸, R⁹) -CQ⁴-, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-, -C (R⁸) = N-, -Q³-CQ⁴-C (R⁸, R⁹) -, -Q³-CQ⁴-N (R¹⁰) -, -Q³-C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -Q³-CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸) = C (R⁸) -N (R¹⁰) -, -C (R⁸) = C (R⁸) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸) = N-N (R¹⁰) -, -Q³-CQ⁴-C (R⁸, R⁹) -N (R¹⁰) -, -Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -

in which
Q³, Q⁴ and Q⁵ are the same or different and each represents oxygen or sulfur,
R⁵ and R⁹ are the same or different and individually represent hydrogen, fluorine, chlorine, methyl or ethyl or together represent ethane-1,2-diyl (dimethylene), and
R¹⁰ for hydrogen, hydroxy, for methyl, ethyl, n- or i-propyl, n-, i-, s- or optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxy carbonyl or ethoxycarbonyl t-butyl, for propenyl, butenyl, propynyl or butynyl, optionally substituted by fluorine, chlorine or bromine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, each optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, Cyclopentylmethyl or cyclohexylmethyl, for methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy or butenyloxy, each optionally substituted by fluorine and / or chlorine, or for each optionally by cyano, fluorine, chlorine, Methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted benzyl or benzyloxy.

The radicals listed above or specified in preferred ranges definitions apply to both the end products of the formula (I) and ent speaking for the respective starting materials or intermediates required for production Products. These residual definitions can be among themselves, that is, between the specified ranges of preferred connections, can be combined as desired.

Examples of the compounds of formula (I) according to the invention are in the groups listed below.  

Group 1

Ar has, for example, the meanings listed below:
2,4-dichlorophenyl, 3-chloro-4-fluorophenyl, 2-chloro-4-cyano-phenyl, 2-fluoro-4-cyano-phenyl, 4,5-difluorophenyl, 2,4, 5-trichlorophenyl, 2,4-dichloro-5-fluorophenyl, 2-chloro-4,5-difluorophenyl, 4-chloro-2,5-difluorophenyl, 5-chloro-2,4-difluoro phenyl, 2-fluoro-5-chloro-4-cyano-phenyl, 2,4,5-trifluorophenyl, 2,5-dichloro-4-cyano-phenyl, 2-chloro-5-fluoro-4-cyano- phenyl, 2-chloro-4,5-dicyano-phenyl, 2-chloro-4-fluoro-5-cyano-phenyl, 2,5-difluoro-4-cyano-phenyl, 4-cyano-3-methyl phenyl, 2 -Chlor-4-cyano-5-methylphenyl, 2,4-dichloro-5-methoxyphenyl, 2,4-dichloro-5-ethoxyphenyl, 2,4-dichloro-5-n-propoxyphenyl , 2,4-dichloro-5-i-propoxyphenyl, 4-chloro-2-fluoro-5-methoxyphenyl, 4-chloro-2-fluoro-5-ethoxyphenyl, 4-chloro-2-fluoro 5-n-propoxy-phenyl, 4-chloro-2-fluoro-5-i-propoxy-phenyl, 2-fluoro-4-cyano-5-methyl-phenyl, 2,4-dichloro-5-methyl-phenyl, 2-chloro-4-cyano-5-trifluoromethyl-phenyl, 4-fluoro-3-trifluoromethyl-phenyl, 2-fluoro-4-cyano-5-trifluoromethylphenyl, 2-chloro-4-methyl-5-trifluoromethyl- phenyl, 2-chlorine -5-fluoro-4-methoxyphenyl, 2-fluoro-4-methoxy-5-methylphenyl, 2,5-difluoro-4-thiocarbamoylphenyl, 2-chloro-4-fluoro-5-i-propoxy- 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-fluoro-4-chloro-5- (1-methyl-2-propynyloxy) phenyl, 2-chloro-4 -thiocarbamoyl-5-i-propoxy-phenyl, 2-fluoro-4-cyano- 5- (2-propenyloxy) phenyl, 2-fluoro-4-chloro-5- (2-propenyloxy) phenyl, 2-chloro -4-cyano- 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-cyano-5-i-propylsulfonylamino-phenyl, 2-chloro-4-thiocarbamoyl-5-ethylsulfonylamino-phenyl, 2 -Chlor-4-cyano-5-cyanaminophenyl, 2-fluoro-4-cyano- 5- (2,2-difluoroethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5-phenylsulfonylaminophenyl, 2-fluorine -4-cyano-5-t-butylsulfonyl amino-phenyl, 2-chloro-4-cyano-5-methoxycarbonyl-phenyl, 2-fluoro-4-cyano-5-ethoxycarbonyl-phenyl, 2-fluoro-4-chloro-5-ethoxycar bonyl-phenyl, 2- Fluoro-4-thiocarbamoyl-5-methoxycarbonyl-phenyl, 2-chloro-4-cyano-5- (N-cyclopropyl-ethylsulfonylamino) -phenyl, 2-fluoro-4-cyano-5- (1-methyl-2-propynylthio ) -phenyl, 2-fluoro-4-cyano-5-methylamino-phenyl, 2-chloro-4-thio carbamoyl-5-methoxycarbonylmethyl-phenyl, 2-chloro-4-cyano-5- (N-methyl-ethyl sulfonylamino ) -phenyl, 2-fluoro-4-cyano-5-i-propoxycarbonyl-phenyl, 2-fluoro-4-chloro-5-i-propoxycarbonyl-phenyl, 2-fluoro-4-cyano-5- (bis-ethylsulfonylamino ) -phenyl, 2-fluoro-4-cyano-5- (N-methylsulfonyl-ethylsulfonylamino) -phenyl, 2-fluoro-4-cyano-5- (1-methoxycarbonyl-ethoxy) -phenyl, 2-fluoro-4 -cyano-5- (1-ethoxycarbonylethoxy) phenyl, 2-fluoro-4-chloro-5- (1-methoxycarbonylethoxy) phenyl, 2-fluoro-4-chloro-5- (1-ethoxycarbonylethoxy ) -phenyl, 2-fluoro-4-cyano-5-cyclopropyloxy-phenyl, 2-chloro-4-cyano-5-dimethylamino-phenyl, 2-fluoro-4-cyano-tetrahydrofuryl methoxy-phen yl, 4-chloro-2-fluoro-tetrahydrofurylmethoxy-phenyl, 2-fluoro-4-cyano-5-aminophenyl, 2-fluoro-4-cyano-5-methylaminocarbonyl-phenyl, 2-fluoro-4-cyano- 5-methylsulfonyloxyphenyl, 2-chloro-4-cyano-5-difluoromethoxyphenyl, 2-fluoro-4-chloro-5-methoxycarbonylmethoxyphenyl, 2-fluoro-4-chloro-5-ethoxycarbonylmeth oxyphenyl, 2 -Fluoro-4-cyano-5-methoxycarbonylmethoxy-phenyl, 2-fluoro-4-cyano-5-ethoxycarbonylmethoxy-phenyl, 4-cyano-3- (1-methyl-2-propynyloxy) phenyl, 2-fluoro-4 -cyano-5-dimethylaminocarbonyl-phenyl, 2-fluoro-4-cyano-5-cyanomethoxy phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-propenyloxy) phenyl, 2-fluoro-4- cyano-5-hydroxy-phenyl, 2-fluoro-4-cyano-5-nitro-phenyl, 2-fluoro-4-cyano-5-diethoxyphos phorylamino-phenyl, 2-fluoro-4-cyano-5-chlorosulfonyl-phenyl , 2-fluoro-4-cyano-5-formylamino-phenyl, 2-chloro-4-cyano-5-ethoxycarbonyloxy-phenyl, 2-fluoro-4-cyano-5-diethoxyphosphorylmethoxy-phenyl, 4-chloro-2-fluorine -5-diethoxyphosphorylmethoxyphenyl, 2-fluoro-4-cyano-5- (1-diethoxyphosphorylethoxy) phenyl, 4-C hlor-2-fluoro-5- (1-diethoxyphosphorylethoxy) phenyl, 2-chloro-4-cyano-5-hydroxyphenyl, 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-ethoxymethyleneamino -phenyl, 2-fluoro-4-cyano-5- (2-chloro-ethoxycarbonyl oxy) -phenyl, 2-chloro-4-cyano-5-dimethylamnomethyleneamino-phenyl, 2-chloro-4-cyano-5- (perhydropyran -4-yloxy) phenyl, 2-fluoro-4-cyano-5- (2-methoxycarbonylethyl) phenyl, 4-chloro-2-fluoro-5- (2-methoxycarbonylethyl) phenyl, 2-chloro - 4-cyano-5- (2-carboxy-2-chloroethyl) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-methoxy carbonyl-ethyl) phenyl, 2-fluoro- 4-chloro-5- (2-chloro-2-methoxycarbonyl-ethyl) -phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-ethoxycarbonyl-ethyl) -phenyl, 2-fluoro-4 -chloro 5- (2-chloro-2-ethoxycarbonyl-ethyl) phenyl, 2-fluoro-4-cyano -5- (2-bromo-2-methoxycarbonyl-ethyl) -phenyl, 2-fluoro-4-chloro-5- (2-bromo-2-methoxycarbonyl-ethyl) -phenyl, 2-fluoro-4-cyano- 5- (2-bromo-2-ethoxycarbonyl-ethyl) phenyl, 2-fluoro-4-chloro-5- (2-bromo-2-ethoxycarbonyl-ethyl) phenyl, 2-fluoro-4-cyano-5- (2,3-dibromo-2-methoxycarbonyl-ethyl) phenyl, 2-fluoro-4-chloro-5- (2,3-dibromo-2-methoxycarbonyl-ethyl) phenyl, 2-fluoro-4-cyano- 5- (2,3-dibromo-2-ethoxycarbonyl-ethyl) -phenyl, 2-fluoro-4-chloro-5- (2,3-dibromo-2-ethoxycarbonyl-ethyl) -phenyl, 2-fluoro-4- cyano-5- (2-chloro-2-s-butoxycarbonyl) 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-cyano-5- (1,2-dibromo-2-methoxycarbony-ethyl) phenyl, 2-chloro -4-cyano-5- (2-chloro-2-i-propoxycarbonyl-ethyl) -phenyl, 2,4-dichloro-5- (2-methoxycarbony-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) -ph enyl, 2-fluoro-4-cyano-5- (2-methoxycarbonyl-ethenyl) phenyl, 2-fluoro-4-chloro-5- (2-methoxycarbonyl-ethenyl) phenyl, 2-fluoro-4-cyano- 5- (2-ethoxy carbonyl-ethenyl) phenyl, 2-fluoro-4-chloro-5- (2-ethoxycarbonyl-ethenyl) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2- methylaminocarbonyl-ethyl) phenyl, 2-fluoro-4-cyano- 5- (2-chloro-2-ethylaminocarbonyl-ethyl) -phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-cyclo propylaminocarbonyl -ethyl) -phenyl, 2-fluoro-4-chloro-5- (2-chloro-methylaminocarbonyl-ethyl) -phenyl, 2-fluoro-4-chloro-5- (2-chloro-2-ethylaminocarbonyl-ethyl) -phenyl, 2-fluoro-4-chloro-5- (2-chloro-2-cyclopropylaminocarbonyl-ethyl) -phenyl, - 2-fluoro-4-cyano-5- (2-chloro-2-dimethylaminocarbonyl-ethyl) - phenyl, 2-fluoro-4-cyano- 5- (2-chloro-2-ethylsulfonylaminocarbonyl-ethyl) -phenyl, 2-fluoro-4-chloro-5- (2-chloro-2-ethylsulfonylaminocarbonyl-ethyl) -phenyl, 2-fluoro-4-chloro-5- (2-carboxyethenyl) phenyl, 2-fluoro-4-thiocarbamoyl-5- (2-ethylaminocarbonylethenyl) phenyl, 2,6-difluoro-4-cyano-5 -i-propoxy-phenyl, 2-chloro-4-cyano-6-fluor -3-i-propoxy-phenyl, 2-chloro-6-fluoro-3-i-propoxy-4-trifluoromethyl-phenyl, 2,6-dichloro-4-cyano-3-fluorophenyl, 2-fluoro-4- cyano-5- (1-ethoxycarbonyl-ethyl) -phenyl, 2-chloro-4-cyano- 5- (1-ethoxycarbonyl-ethyl) -phenyl, 2-chloro-4-cyano-4-carboxy-phenyl, 2- Fluoro-4-chloro-5- (1-ethoxycarbonyl-ethyl) phenyl, 2-fluoro-4-chloro-5- (1-i-propoxycarbonyl-ethyl) 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, 2-fluoro-4-chloro-5 - (2-methoxyethoxy) phenyl, 2-fluoro-4-chloro-5-i-butoxyphenyl, 4-hydroxy-4-ethoxycarbonylphenyl, 2-fluoro-4-cyano-5-i-propoxycarbonylphenyl , 2-fluoro-4-hydroxy-5-i-propoxycarbonylphenyl, 2-fluoro-4-cyano-5- (2-oxetanyloxy) phenyl, 2-fluoro-4-cyano-5- (2-oxetanyloxycarbonymethoxy) phenyl, 2-fluoro-4-cyano-5- (2-oxetanyl oxy) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-propenyloxy) phenyl, 4-chloro-2-fluoro - 5- (2-chloro-2-propenyloxy) phenyl, 2-fluoro-4-chloro-5-methoxycarbonylmethylthio-phenyl, 2-fluoro-4-chloro-5-ethoxycarbon ylmethylthio-phenyl, 2-fluoro-4-cyano-5-meth oxycarbonylmethylthio-phenyl, 2-fluoro-4-cyano-5-ethoxycarbonylmethylthio-phenyl, 2-fluoro-4-chloro-5- (1-methoxycarbonyl-ethylthio ) -phenyl, 2-fluoro-4-chloro-5- (1-ethoxycarbonyl-ethylthio) -phenyl, 2-fluoro-4-cyano-5- (1-methoxycarbony-ethylthio) phenyl, 2-fluoro-4- cyano-5- (1-ethoxycarbonyl-ethylthio) phenyl,

R stands for example for hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, allyl, propargyl, methoxy, ethoxy, n- or i-propoxy, Cyanomethyl, carboxymethyl, methoxymethyl, ethoxymethyl, methoxycarbo nylmethyl, ethoxycarbonylmethyl, acetyl, propionyl, methoxycarbonyl, ethoxy carbonyl, methylsulfonyl or ethylsulfonyl.  

Group 2

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

Group 3

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

Group 4

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

Group 5

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

Group 6

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

Group 7

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

Group 8

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

Group 9

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

Group 10

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

Group 11

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

Group 12

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

Group 13

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

Group 14

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

Group 15

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

Group 16

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

Group 17

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

Group 18

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

Group 19

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

Group 20

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

Group 21

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

Group 22

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

Group 23

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

Group 24

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

Group 25

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

Group 26

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

Group 27

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

Group 28

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

Group 29

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

Group 30

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

Group 31

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

Group 32

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

Group 33

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

Group 34

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

Group 35

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

Group 36

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

Group 37

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

Group 38

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

Group 39

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

Group 40

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

Group 41

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

Group 42

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

Group 43

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

Group 44

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

Group 45

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

Group 46

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

Group 47

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

Group 48

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

Group 49

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

Group 50

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

Group 51

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

Group 52

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

Group 53

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

Group 54

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

Group 55

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

Group 56

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

Group 57

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

Group 58

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

Group 59

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

Group 60

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

Group 61

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

Group 62

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

Group 63

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

Group 64

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

Group 65

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

Group 66

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

Group 67

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

Group 68

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

Group 69

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

Group 70

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

Group 71

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

Group 72

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

Group 73

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

Group 74

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

Group 75

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

Group 76

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

Group 77

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

Group 78

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

Group 79

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

Group 80

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

Group 81

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

Group 82

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

Group 83

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

Group 84

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

If, for example, 1- (4-cyano-2,5-difluorophenyl) -2-methyltriazolidine is used 3,5-dithione and chlorodifluoromethane as starting materials, so the reaction sequence in process (a) according to the invention using the following formula are reproduced:

For example, 4-methyl-2-i-propyl-5-thioxo-triazolidin-3-one and 2-ethoxy-4,5-difluoro-benzonitrile as starting materials, so the reaction can in the process (b) according to the invention outlined by the following formula will:

For example, if 1- (2,4-dichloro-5-methoxycarbonyl-phenyl) - 2-methyl-4-i-propyl-semicarbazide and phosgene as starting materials, so the Re Action sequence in the method (c) according to the invention by the following formula scheme are outlined:

The process (a) according to the invention for the preparation of the compounds of general formula (I) to be used as starting materials (thio) urazole deri vate are generally defined by formula (II). In formula (II) Q¹, Q² and Ar preferably or in particular those meanings that already above in connection with the description of the compounds of the formula (I) stated as preferred or as particularly preferred for Q 1, Q 2 and Ar were; A¹ and A² are hydrogen or preferably or ins special ones meanings above in connection with the Be writing the compounds of formula (I) as preferred or as particular were preferably given for R¹ and R², but at least one of the Groups A¹ or A² is hydrogen.

The starting materials of formula (II) are known and / or can be known Processes are produced (cf. EP 55105, production examples).

The (thio) urazole derivatives of the formula (II) are obtained if
(a) aryl (thio) semicarbazide derivatives of the general formula (VII)

in which
Ar, Q¹ and Q² have the meanings given above and
R represents alkyl,
optionally in the presence of a reaction auxiliary, such as. As sodium or potassium hydroxide, and optionally in the presence of a diluent, such as. B. water, cyclizing condensed and, if appropriate, subsequently carrying out electrophilic or nucleophilic substitution reactions as part of the definition of the substituent (cf. J. Org. Chem. 56 (1991), 5643-5651, EP 55105, EP 246749).

or if you
(b) aryl (thio) semicarbazides of the general formula (VIII)

in which
A¹, A², Ar and Q¹ have the meaning given above,
with (thio) phosgene optionally in the presence of a reaction auxiliary, such as. As magnesium oxide, and optionally in the presence of a diluent, such as. B. toluene, and optionally subsequently electrophilic or nucleophilic sub stitution reactions in the context of the substituent definition in the usual way (see. DE 44 16 868).

The precursors of formulas (VII) and (VIII) are known and / or can according to known methods can be prepared (cf. J. Org. Chem. 56 (1991), 5643-5651, EP 55105, EP 246749, DE 44 16 868).

The process (a) according to the invention for the preparation of the compounds of general formula (I) to be used as starting materials alkylation means are generally defined by formulas (IIIa) and (IIIb). In the formula (IIIa) and (IIIb) R 1 and R 2 preferably or in particular have those interpretations that have already been made in connection with the description of the ver Bonds of formula (I) as preferred or as particularly preferred for R¹ and R² have been given; X preferably represents fluorine, chlorine, bromine or iodine, especially for chlorine or bromine.

The starting materials of the formulas (IIIa) and (IIIb) are known organic Synthetic chemicals.  

Process (a) according to the invention is preferably used in the presence of a Neten reaction auxiliary carried out. As such, all the usual ones arrive organic or organic bases in question. These include, for example, alkali metal or alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates, such as lithium, sodium, Potassium or calcium hydride, lithium, sodium or potassium amide, sodium or Potassium methylate, sodium or potassium ethylate, sodium or potassium propylate, aluminum isopropoxide, sodium or potassium tert-butoxide, sodium or Potassium hydroxide, ammonium hydroxide, sodium, potassium or calcium acetate, Ammonium acetate, sodium, potassium, rubidium, cesium, magnesium or Calcium carbonate, ammonium carbonate, sodium or potassium hydrogen carbonate, and basic organic nitrogen compounds, such as trimethylamine, triethyl amine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethylcyclo hexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl and 4-methyl-pyridine, 2,4-di methyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5-ethyl 2-methyl-pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

As a diluent for carrying out process (a) according to the invention the usual organic solvents come into consideration. This includes ins special aliphatic, alicyclic or aromatic, optionally halogenated Hydrocarbons, such as pentane, hexane, heptane, petroleum ether, Ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, Methylcyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as Di ethyl ether, diisopropyl ether, t-butyl methyl ether, t-pentyl methyl ether, dioxane, Tetrahydrofuran, ethylene glycol dimethyl or diethyl ether, diethylene glycol dimethyl ether or diethyl ether, ketones such as acetone, butanone or methyl iso butyl ketone; Nitriles, such as acetonitrile, propionitrile, butyronitrile or benzonitrile, Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide, esters such as vinegar acid methyl ester, ethyl ester, n- or i-propyl ester, n-, i- or s-butyl ester, Sulfoxides, such as dimethyl sulfoxide, alcohols, such as methanol, ethanol, n- or i-Pro panol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether or monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, the Mix with water or pure water.  

The reaction temperatures can be carried out when carrying out the process according to the invention Process (a) can be varied over a wide range. Generally works one at temperatures between 0 ° C and + 200 ° C, preferably at temperatures between 10 ° C and 150 ° C.

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

In general, to carry out process (a) according to the invention the starting materials of the formulas (II) and (IIIa) or (IIIb) in a suitable Diluent submitted and after adding a reaction aid - at the required temperature until the end of the reaction. The on work can be done in the usual way.

The process (b) according to the invention for the preparation of the compounds of general formula (I) to be used as starting materials (thio) urazoles generally defined by formula (IV). In formula (IV) Q¹, Q², R¹ have and R² preferably or in particular those meanings which have already been given above in connection with the description of the compounds of formula (I) as be preferred or indicated as particularly preferred for Q¹, Q², R¹ and R² were.

The starting materials of formula (IV) are known and / or can be known Processes are prepared (see J. Org. Chem. 56 (1991), 5643-5651, DE 44 16 868).

The process (b) according to the invention for the preparation of the compounds of general formula (I) haloarenes to be used as starting materials are generally defined by the formula (V). Ar is preferred in formula (V) wise or in particular the meaning that is already related above with the description of the compounds of formula (I) as preferred or ins was particularly preferred for Ar; X preferably represents fluorine, Chlorine or bromine, especially for fluorine or chlorine.

The starting materials of the formula (V) are known and / or can be known Processes are produced (cf. EP 191181, EP 441004, EP 431373).  

Process (b) according to the invention is optionally carried out in the presence of a Reaction auxiliary carried out. The same reaction occurs here auxiliaries as in method (a) according to the invention.

Process (b) according to the invention is preferably carried out using a Diluent carried out. The same dilutions come here medium as in process (a) according to the invention.

The reaction temperatures can be carried out when carrying out the process according to the invention Process (b) can be varied over a wide range. Generally works one at temperatures between 0 ° C and + 200 ° C, preferably at temperatures between 20 ° C and 150 ° C.

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

To carry out process (b) according to the invention, in general the starting materials of formula (IV) and (V) in a suitable dilution submitted medium and after adding a suitable reaction auxiliary at required temperature until the end of the reaction. The workup can be done in the usual way.

The process (c) according to the invention for the preparation of the compounds of general formula (I) aryl (thio) semicarb to be used as starting materials Azides are generally defined by the formula (VI). In formula (VI) Ar, Q¹, R¹ and R² preferably or in particular those meanings which already above in connection with the description of the connections of the Formula (I) as preferred or as particularly preferred for Ar, Q¹, R¹ and R² were specified.

The starting materials of the formula (VI) are known and / or can be known Processes are prepared (see. Houben-Weyl, Volume 9, 909; Org. Synth., Coll. Vol. 3 (1955), 360).  

Process (c) according to the invention is optionally carried out in the presence of a Reaction auxiliary carried out. The same reaction occurs here auxiliaries as in method (a) according to the invention.

Process (c) according to the invention is preferably carried out using a Diluent carried out. The same dilutions come here medium as in process (a) according to the invention.

The reaction temperatures can be carried out when carrying out the process according to the invention Process (c) can be varied over a wide range. Generally works one at temperatures between 0 ° C and + 150 ° C, preferably at temperatures between 10 ° C and 100 ° C.

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

In general, the process (c) according to the invention is carried out the starting materials of formula (VI) in a suitable diluent sets and - if necessary after adding a suitable reaction auxiliary - phosgene or thiophosgene is slowly added. The reaction mixture is then stirred at the required temperature until the end of the reaction. The Refurbishment can be carried out in the usual way.

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 in places grow up where they are undesirable. Whether the substances according to the invention as total or selective herbicides act essentially depends on the applied Amount off.

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

Dicot 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.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, sorghum, panicum, saccharum, pineapple, asparagus, allium.

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

Depending on the concentration, the compounds are suitable for the total weed control z. B. on industrial and track systems and on paths and Places with and without tree cover. Likewise, the connections to Weed control in permanent crops, e.g. B. forest, ornamental trees, fruit, wine, Citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and Hop plants, on ornamental and sports turf and pastures and for selective Weed control can be used in annual crops.

The compounds of formula (I) according to the invention are particularly suitable for selective control of monocot and dicot weeds in mono cotyledonous and dicotyledon cultures both in the pre- and post-emergence Method.

Furthermore, the compounds of the formula (I) according to the invention also show strong ones insecticidal activity, especially against beetle larvae, such as B. Phaedon cochleariae.  

The active ingredients are suitable for good plant tolerance and inexpensive warmth blood toxicity to control animal pests, especially insects, Arachnids and nematodes, which are used in agriculture, in forests, in stock and Material protection and in the hygiene sector. You can before are preferably used as pesticides. You are against normal sen sible and resistant species as well as against all or individual stages of development effective. The pests mentioned above include:

From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Por cellio scaber.

From the order of the Diplopoda z. B. Blaniulus guttulatus.

From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spec.

From the order of the Symphyla z. B. Scutigerella immaculata.

From the order of the Thysanura z. B. Lepisma saccharina.

From the order of the Collembola z. B. Onychiurus armatus.

From the order of Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermaptera z. B. Auricular Forficula.

From the order of the Isoptera z. B. Reticulitermes spp.

From the order of the Anoplura z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.  

From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euprocti chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabroti ca spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus 37147 00070 552 001000280000000200012000285913703600040 0002019601626 00004 37028, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Aihphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.  

From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophlla melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.

From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.

From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

The plant parasitic nematodes include z. B. Pratylenchus spp., Radopho lus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., xiphinema spp., Trichodorus spp.

Mixing partners suitable for use are e.g. B. the following:

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanide; 2,6-di chloroN- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,
Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram,
Dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
Edifenphos, epoxyconazole, ethirimol, etridiazole,
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanyl, Fuberilafil, Fuberri Furmecyclox,
Guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,
Kasugamycin, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
Quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Validamycin A, vinclozolin,
Zineb, ziram

Bactericides

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, Kasugamy cin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, Tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides

Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alpha methrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Buto carboxin, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlor fluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocy thrin, Chrinophhrinhrhrinhrin, chrinophhrin, chrinophhrin, chrinophhrin, chrinophhrin, chrinophhrin, chrinophhrin , Cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothxinfox, Fufionophon, Fufionophon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufon
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, NI 25, Nitenpyram
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophhine, Pyrachlophhion, Pyrachlophion, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophion Pyridaben, pyrimidifen, pyriproxifen,
Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio methon, Thionazin, Thuringiensin, Tralomichonon, Triaromenontron, Triaromenontron, Triarathenlarbon, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triarathenltronium, Triaromenontrin, Triarathenltronium, Triaromenontrin, Triarathenltron, Triaromenontron
Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.

The active compounds according to the invention can also be used in their commercially available form formulations and in the application forms prepared from these formulations in a mixture with synergists. Synergists are connections through which the effect of the active ingredients is increased without the added synergist must be actively active itself.

The active ingredient content of the prepared from the commercially available formulations Application forms can vary widely. The drug concentration the use forms can be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.

The application takes place in a customary manner adapted to the application forms Wise.

When used against hygiene and storage pests, the stands out Active ingredient through an excellent residual effect on wood and clay as well due to good stability to alkali on limed substrates.

The active compounds according to the invention act not only against plant, hygiene and Pests, but also against the veterinary sector animal parasites (ectoparasites) such as tortoise ticks, leather ticks, mite mites, Running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings and fleas. These parasites include:

From the order of the Anoplurida z. B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.  

From the order of the Mallophagida and the subordinates Amblycerina as well Ischnocerina e.g. B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.

From the order Diptera and the subordinates Nematocerina as well Brachycerina e.g. B. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida z. B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida z. B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida z. B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.

From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata e.g. B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) z. B. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.  

The active compounds of the formula (I) according to the invention are also suitable for combating Examination of arthropods, the farm animals, such as. B. cattle, sheep, Goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, Geese, bees, other pets such as B. dogs, cats, house birds, Aquarium fish and so-called experimental animals, such as. B. hamster, sea pigs, rats and mice. By fighting this arthro deaths and reduced performance (for meat, milk, wool, Hides, eggs, honey, etc.) can be reduced, so that by using the Active ingredients according to the invention a more economical and easier animal husbandry is possible.

The active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, Tab Latvian, capsules, watering, drenching, granules, pastes, boluses, feed-through Method, of suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), Im plantate, by nasal application, by dermal application in the form of for example diving or bathing (dipping), spraying (spray), pouring on (Pour-on and spot-on), washing, powdering and with the help of active molded articles, such as collars, ear tags, tail tags, link measuring tapes, holsters, marking devices etc.

When used for cattle, poultry, pets etc. you can use the active ingredients of the formula (I) as formulations (for example powders, emulsions, flowable Agents), which contain the active ingredients in an amount of 1 to 80 wt .-%, directly or after 100 to 10,000 times dilution or as chemical Use bath.

It has also been found that the compounds of the formula (I) show a high insecticidal activity against insects, the technical mate destroy rialien.

The following insects may be mentioned by way of example and preferably, but without limitation:
Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollicesis, Lyctusollisellisques, Lyctusollisoxisquelixes, Lyctusollisisis, Lyctusollisisis Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus;
Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
Bristle tails, such as Lepisma saccarina.

In the present context, technical materials include non-living ones Understand materials, such as preferably plastics, adhesives, glues, Paper and cardboard, leather, wood and wood processing products and paint medium.

It is very particularly preferred to prevent insect attack protective material around wood and wood processing products.

Among wood and wood processing products, which by the invention Agents or mixtures containing them can be protected is exemplary to understand: timber, wooden beams, railway sleepers, bridge parts, jetties, Wooden vehicles, boxes, pallets, containers, telephone poles, wooden panels, Wooden windows and doors, plywood, chipboard, carpentry or wood pro products that are used in general in house construction or in joinery Find.

The active ingredients can be used as such, in the form of concentrates or in general usual formulations such as powders, granules, solutions, suspensions, emul sions or pastes.

The formulations mentioned can be prepared in a manner known per se be, e.g. B. by mixing the active ingredients with at least one solution or Diluent, emulsifier, dispersing and / or binding or fixing agent  tels, water repellants, possibly desiccants and UV stabilizers and opp if necessary dyes and pigments and other processing aids.

The insecticidal agents used to protect wood and wood-based materials or concentrates contain the active ingredient according to the invention in a concentra tration from 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.

The amount of agents or concentrates used depends on the type and type come from insects and depending on the medium. The optimal amount to use can be determined by test series in the application. Generally in my opinion, however, it is sufficient 0.0001 to 20% by weight, preferably 0.001 to 10 wt .-%, of the active ingredient, based on the material to be protected.

An organic chemical solvent serves as the solvent and / or diluent solvent or solvent mixture and / or an oily or oily heavy volatile organic chemical solvent or solvent mixture and / or a polar organic chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.

The organic chemical solvents used are preferably oily or oily ones Solvents with an evaporation number above 35 and a flash point above half 30 ° C, preferably above 45 ° C, used. As such volatile, water-insoluble, oily and oily solvents become corresponding mine ralöle or their aromatic fractions or mineral oil-containing solvent mixtures cal, preferably white spirit, petroleum and / or alkylbenzene used.

Mineral oils with a boiling range of 170 to 220 ° C are advantageous, test petrol with a boiling range of 170 to 220 ° C, spindle oil with a boil range from 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 up to 280 ° C, turpentine oil and the like.

In a preferred embodiment, liquid aliphatic hydrocarbons substances with a boiling range of 180 to 210 ° C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C and / or locker oil and / or monochloronaphthalene, preferably two se α-monochloronaphthalene used.  

The organic non-volatile oily or oily solvents with a Evaporation rate above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partly due to slightly or medium-volatile organic chemistry cal solvents are replaced, with the proviso that the solvent Ge also mix an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide fungicide Mixture is soluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, part of the organic chemical Solvent or solvent mixture or an aliphatic polar orga niche chemical solvent or solvent mixture replaced. Preferably come alipha containing hydroxyl and / or ester and / or ether groups organic chemical solvents such as glycol ether, esters or the like for use.

As an organic chemical binder in the present Er finding the known water-dilutable and / or in the used organic chemical solvents soluble or dispersing or emul gable synthetic resins and / or binding drying oils, especially binders consisting of or containing an acrylic resin, a vinyl resin, e.g. B. polyvinyl acetate, Polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene Coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or Resin used.

The synthetic resin used as a binder can be in the form of an emulsion, disper sion or solution. Bitumen or bituminous substances up to 10 wt .-%, are used. In addition, you can dyes, pigments, water-repellants, odor correctors known per se tien and inhibitors or corrosion protection agents and the like. Be used.

According to the invention, preference is given to organic chemical binders least an alkyd resin or modified alkyd resin and / or a drying one vegetable oil contained in the medium or in the concentrate. According to the invention alkyd resins with an oil content of more than 45 wt .-%, preferably 50 to 68% by weight.  

The binder mentioned can be wholly or partly by a fixation medium (mixture) or a plasticizer (mixture) can be replaced. These additions should volatilize the active ingredients and crystallize or from prevent falling. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

The plasticizers come from the chemical classes of phthalic acid esters such as Dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ether or higher molecular weight Gly kolether, glycerol ester and p-toluenesulfonic acid ester.

Fixing agents are chemically based on polyvinyl alkyl ethers such as. B. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.

Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above organic chemical solvents or diluents, emulsifiers and dispersers gators.

A particularly effective wood protection is provided by industrial impregnation drive, e.g. B. vacuum, double vacuum or printing process.

The ready-to-use agents can optionally also be other insecticides and optionally contain one or more fungicides.

The additional mixing partners are preferably those in WO 94/29 268 Insecticides and fungicides mentioned in question. The ones mentioned in this document Connections are an integral part of this application.

Insecticides such as chlorine pyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, delta methrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and tri flumuron can be used as very particularly preferred mixing partners.
as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro octylisothiazolin-3-one.

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 polymeric fabrics.

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 carbons Hydrogen, 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 cyclo hexanone, 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, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks like Calcite, marble, pumice, sepiolite, dolomite and synthetic granules from an organic and organic flours and granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or Foaming agents are possible: B. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fat alcohol ether, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl  sulfonates and protein hydrolyzates; as dispersants come into question: z. B. Lignin sulfite liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations Liche and synthetic powdery, granular or latex-shaped polymers used such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids 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, Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalalo cyanine 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 weight percent active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their form in mixtures with known herbicides for weed control Ver find application, whereby finished formulations or tank mixes are possible.

Known herbicides are suitable for the mixtures, for example anilides, such as B. Diflufenican and Propanil; Arylcarboxylic acids, such as. B. dichloropicolin acid, dicamba and picloram; Aryloxyalkanoic acids, such as. B. 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as B. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones, such as B. Chloridazon and Norflurazon; Carbamates, such as B. Chlorpropham, Desmedipham, Phenmedipham and Propham; Chloroacet anilides, such as B. alachlor, acetochlor, butachlor, metazachlor, metolachlor, Pretilachlor and propachlor; Dinitroanilines such as e.g. B. Oryzalin, Pendimethalin and Trifluralin; Diphenyl ether, such as. B. acifluorfen, bifenox, fluoroglycofen, Fomesafen, halosafen, lactofen and oxyfluorfen; Ureas, such as B. chlorine toluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines, such as. B. Alloxydim, Clethodim, Cycloxydim, Sethoxydim and Tralkoxydim; Imidazolinones, e.g. B. Imazethapyr, Imazamethabenz, Imazapyr and imazaquin; Nitriles such as B. bromoxynil, dichlobenil and ioxynil; Oxyacet amides such as B. Mefenacet; Sulfonylureas, such as. B. amidosulfuron,  Bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, Triasulfuron and tribenuron-methyl; Thiol carbamates such as e.g. B. butylates, cycloates, Dialallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; Triazines, e.g. B. Atrazin, Cyanazin, Simazin, Simetryne, Terbutryne and Terbutylazin; Triazinones such as e.g. B. hexazinone, metamitron and metribuzin; Others, such as B. aminotriazole, benfuresate, bentazone, cinmethylin, cloma zone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridones, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and tridiphanes.

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 will. 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 the up run of the plants can be applied. You can also sow in the soil before sowing be incorporated.

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.

Manufacturing examples example 1

1.8 g (6 mmol) 1 - (- 2-fluoro-4-cyano-5-but-1-in-3-yl-oxy-phenyl) -2-methyl- 3,5-dioxo-1,2,4-triazole and 1.1 g (8 mmol) of potassium carbonate are dissolved in 50 ml Dimethyl sulfoxide stirred for one hour at 60 ° C, to room temperature (approx. 20 ° C) cooled, mixed with 1.1 g (8 mol) of methyl iodide and 12 hours in the room temperature stirred. The mixture is concentrated under reduced pressure Residue stirred with water, with conc. Hydrochloric acid adjusted to pH 5 and that precipitated product isolated by filtration.

0.7 g (28% of theory) of 1 - (- 2-fluoro-4-cyano-5-but-1-in-3-yl-oxy- phenyl) -2,4-dimethyl-3,5-dioxo-1,2,4-triazole, melting point 157 ° C.  

Example 2

4.8 g (18 mmol) 1 - (- 2,5-difluoro-4-cyano-phenyl) -2,4-dimethyl-3,5-dioxo- 1,2,4-triazole and 2.8 g (20 mmol) of potassium carbonate are dissolved in 100 ml of dimethyl sulfoxide 2.2 g (20 mmol) of ethanesulfonamide were added and the mixture was stirred at 120 ° C. for 4 hours. The mixture cooled to 25 ° C is stirred with ice water, with conc. Salt acid adjusted to pH 5 and the precipitated product isolated by filtration.

5.2 g (81% of theory) of 1- (2-fluoro-4-cyano-5-ethylsulfonylamino) are obtained phenyl) -2,4-dimethyl-3,5-dioxo-1,2,4-triazole, melting point 203 ° C.

Analogous to Examples 1 and 2 and in accordance with the general Be Description of the manufacturing process according to the invention can for example also the compounds of the formula (I) listed in Table 1 below getting produced.

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

Starting materials of formula (II) Example (II-1)

5.8 g (50 mmol) of 1-methyl-3,5-dioxo-1,2,4-triazole and 7.6 g (55 mmol) of potassium Carbonate in 150 ml of dimethyl sulfoxide with 8.6 g (55 mmol) of 2,4,5-trifluoro benzonitrile were added and the mixture was stirred at 120 ° C. for 12 hours. The cooled down to 25 ° C Mixture is concentrated under reduced pressure, the residue with water stirred, with conc. Hydrochloric acid adjusted to pH 5 and the precipitated product isolated by filtration.

11.8 g (94% of theory) of 1 - (- 2,5-difluoro-4-cyano-phenyl) - are obtained 2-methyl-3,5-dioxo-1,2,4-triazole, melting point 218 ° C.

Example (II-2)

5.8 g (50 mmol) of 4-methyl-3,5-dioxo-1,2,4-triazole and 13.8 g (100 mmol) of potassium Carbonate in 50 ml of dimethyl sulfoxide with 7.9 g (50 mmol) of 2,4,5-trifluoro benzonitrile were added and the mixture was stirred at 25 ° C. for 12 hours. The cooled down to 25 ° C  Mix is mixed with ice water, with conc. Hydrochloric acid adjusted to pH 5 and the precipitated product is isolated by filtration.

11.1 g (88% of theory) of 1 - (- 2,5-difluoro-4-cyano-phenyl) - are obtained 4-methyl-3,5-dioxo-1,2,4-triazole, melting point 174 ° C.

Example (II-3)

5 g (20 mmol) 1 - (- 2,5-difluoro-4-cyano-phenyl) -2-methyl-3,5-dioxo-1,2,4-triazole with 2.8 g (40 mmol) of butin-1-ol- (3) in 100 ml of acetonitrile at 25 ° C. in portions with 1.2 g (40 mmol) of sodium hydride (80% in paraffin) and stirred for 12 hours at 25 ° C. The mixture is made under reduced pressure concentrated, the residue stirred with water, with conc. Hydrochloric acid to pH 5 provided and the precipitated product isolated by filtration.

4.9 g (82% of theory) of 1 - (- 2-fluoro-4-cyano-5-but-1-yn-3-yl-oxy- phenyl) -2-methyl-3,5-dioxo-1,2,4-triazole, melting point 149 ° C.  

Analogous to Examples (II-1) to (II-3), for example, those in the Compounds of formula (II) listed in Table 2 below will.

Table 2: Examples of the compounds of the formula (II)

Examples of use Example A Pre-emergence test

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

To produce a suitable preparation of active compound, 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 desired concentration.

Seeds of the test plants are sown in normal soil and watered with the active compound preparation after 24 hours. The amount of water per unit area is expediently kept constant. The concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
0% = no effect (like untreated control)
100% = total annihilation.

In this test, for example, the compounds according to the manufacturing example show Game 1 and 14 with good application rates of 250 or 1000 g / ha tolerance to crops, such as. B. corn, cotton and soybeans, and strong action against weeds such as Digitaria (80-100%), Setaria (80-90%), Amaranthus (90-100%), Polygonum (90-100%) and Viola (95-100%).  

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 indicates that given amount of emulsifier and dilute the concentrate with water to the desired concentration.

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

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

In this test, for example, the compounds according to the manufacturing example show Game 1 and 3 at an application rate of 250 g / ha with a partially good contract sensitivity to crops, such as. B. wheat, strong action against Un herbs such as Echinochloa (100%), Setaria (100%), Abutilon (100%), Amaranthus (95-100%) and Polygonum (100%).  

Example C Phaedon larval test

Solvent: 7 parts by weight of dimethylformamide
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 stated amount of solvent and the given amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with horseradish leaf beetle larvae (Phaedon cochleariae) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. Here means 100% that all beetle larvae have been killed; 0% means that no beetles Larvae were killed.

In this test, e.g. B. the connection according to preparation example 14 an active ingredient concentration of 0.1% a degree of killing of 100% after 7 Days.

Claims (8)

1. N-aryl nitrogen heterocycles of the general formula (I) in which
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R¹ for cyano, formyl, for alkyl optionally substituted by halogen, cyano, car boxy, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkoxycarbonyl, alkenyloxycarbonyl or alkynyloxy carbonyl, for each alkenyl or alkynyl optionally substituted by halo, for each alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl or alkylsulfonyl optionally substituted by halogen, or cycloalkyl or cycloalkylcarbonyl optionally substituted by halogen, cyano or carboxy,
R² for amino, cyano, formyl, for each optionally substituted by halo, cyano, carboxy, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkoxycarbonyl, alkenyloxycarbonyl or alkynyloxycarbonyl, alkyl, alkylamino or dialkylamino, each optionally substituted by halogen, substituted alkenyl or alkynyl, in each case optionally substituted by halogen substituted alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alk oxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl or alkyl sulfonyl, or for cycloalkyl or cycloalkylcarbonyl optionally substituted by halogen, cyano or carboxy, and
Ar represents the substituted, monocyclic or bicyclic aryl or heteroaryl group defined below, wherein
R³ represents hydrogen or halogen,
R⁴ represents hydrogen or halogen,
R⁵ stands for cyano, carboxy, chlorocarbonyl, carbamoyl, thiocarb amoyl, hydroxy, halogen or for alkyl, alkoxy or alkoxy carbonyl optionally substituted by halogen,
R⁶ represents the following grouping, -A¹-A²-A³in which
A¹ represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ represents hydrogen, hydroxy, alkyl, alkenyl, alkynyl, alkoxy, aryl, alkylcarbonyl, Arylcarbonyl, alkylsulfonyl or arylsulfonyl,
A¹ furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A² represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ represents hydrogen, hydroxy, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
A² furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A³ represents hydrogen with the proviso that in this case A¹ and / or A² do not represent a single bond
A³ furthermore for hydroxy, mercapto, amino, cyano, isocyano, thio cyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl and alkylamino, each optionally substituted by halogen or alkoxy , Dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl, for alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynyl thio, alkynylamino or alkynyloxycarbonyl, optionally substituted by halogen, cyano, for each optionally substituted by halogen Carboxy, alkyl and / or alkoxy carbonyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, or for each optionally by nitro, cyano, carboxy, halogen, alkyl, haloalkyl, alkyl oxy, haloalkyloxy and / or alkoxycarbonyl substituted aryl, aryloxy, aralkyl, arylalkoxy, A ryloxycarbonyl or arylalkoxy carbonyl,
Farther
A³ for in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimidyl, pyrimyl, tryl Oxazolylalkyl, isoxazolyl alkyl, thiazolylalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furylalkoxy, represents perhydropyranylalkoxy or pyridylalkoxy, and
R⁷ represents hydrogen or halogen,
or two adjacent residues - R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶ or R⁶ and R⁷ - together represent one of the following groups -Q³-CQ⁴-, -Q³-CQ⁴-Q⁵-, -Q³-C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -CQ⁴-, -C (R⁸, R⁹) -Q³-CQ⁴-, -Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -, -Q³ -C (R⁸, R⁹) -C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-, -Q³-C (R⁸) = C (R⁸) -, -C (R⁸) = C (R⁸) -CQ⁴-, -Q³-C (R⁸, R⁹) -CQ⁴-, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-, -C (R⁸) = N -, -Q³-CQ⁴-C (R⁸, R⁹) -, -Q³-CQ⁴-N (R¹⁰) -, -Q³-C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹ ) -Q³-CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴- N (R¹⁰) -, -C (R⁸) = C (R⁸) -N (R¹⁰) -, -C (R⁸) = C (R⁸) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) - CQ⁴-N (R¹⁰) -, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸) = NN (R¹⁰) -, -Q³-CQ⁴-C (R⁸, R⁹) -N (R¹⁰) -, Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) - whereby
Q³, Q⁴ and Q⁵ are the same or different and each represents oxygen or sulfur,
R⁸ and R⁹ are the same or different and individually represent hydrogen, halogen or alkyl or together represent alkanediyl, and
R¹⁰ for hydrogen, hydroxy, for alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl optionally substituted by cyano, halo, alkoxy, alkylcarbonyl or alkoxycarbonyl, for each optionally substituted by halogen alkenyl or alkynyl, for each optionally substituted by halogen or alkyl sub substituted cycloalkyl or cycloalkylalkyl, for alkoxy or alkenyloxy optionally substituted by halogen, or for arylalkyl or arylalkoxy optionally substituted by cyano, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy. 2. N-aryl nitrogen heterocycles of the formula (I) according to claim 1, characterized in that
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R¹ for cyano, formyl, each optionally by fluorine, chlorine, cyano, carboxy, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy, C₁-C₄-alkylthio, C₃-C₄-alkenylthio, C₃ -C₄-alkynylthio, C₁-C₄-alkoxy-carbonyl, C₃-C₄-alkenyloxy-carbonyl or C₃-C₄-alkynyl oxy-carbonyl substituted C₁-C₆-alkyl, for each optionally substituted by fluorine or chlorine substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, for each optionally substituted by fluorine or chlorine-substituted C₁-C₆-alkylcarbonyl, C₃-C₆-alkenyl-carbonyl, C₃-C₆-alkynylcarbonyl, C₁-C₆-alkoxy-carbonyl, C₃-C₆ -Alkenyloxy-carbonyl, C₃-C₆-alkynyloxy-carbonyl or C₁-C₆-alkylsulfonyl, or for C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl which is optionally substituted by fluorine, chlorine, bromine, cyano or carboxy,
R² for amino, cyano, formyl, for each optionally by fluorine, chlorine, cyano, carboxy, C₁-C₄-alkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy, C₁-C₄-alkylthio, C₃-C₄-alkenylthio, C₃-C₄-alkynylthio, C₁-C₄-alkoxy-carbonyl, C₃-C₄-alkenyloxy-carbonyl or C₃-C₄-alkynyloxy-carbonyl-substituted C₁-C₆-alkyl, C₁-C₆-alkylamino or di (C₁-C₄- alkyl) amino, for C₃-C₆-alkenyl or C₃-C₆-alkynyl optionally substituted by fluorine or chlorine, for C₁-C₆-alkylcarbonyl optionally substituted by fluorine or chlorine, C₃-C₆-alkenyl-carbonyl, C₃- C₆-alkynyl-carbonyl, C₁-C₆-alkoxy-carbonyl, C₃-C₆-alkenyloxy-carbonyl, C₃-C₆-alkynyl oxy-carbonyl or C₁-C₆-alkylsulfonyl, or for any given case by fluorine, chlorine, bromine, cyano or carboxy substituted C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-carbonyl, and
Ar represents the substituted, monocyclic or bicyclic aryl or heteroaryl group defined below, wherein
R³ represents hydrogen, fluorine, chlorine or bromine,
R⁴ represents hydrogen, fluorine, chlorine or bromine,
R⁵ represents cyano, carboxy, chlorocarbonyl, carbamoyl, thiocarbamoyl, hydroxy, fluorine, chlorine, bromine or for each optionally substituted by fluorine and / or chlorine alkyl, alkoxy or alkoxycarbonyl, each having up to 4 carbon atoms,
R⁶ represents the following grouping, -A¹-A²-A³in which
A¹ is a single bond, oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ is hydrogen, hydroxy, C₁-C₄-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl, C₁-C₄-alkoxy, phenyl, C₁-C₄-alkylcarbonyl, phenylcarbonyl, C₁-C₄-alkylsulfonyl or phenylsulfonyl,
A¹ furthermore represents C₁-C₆alkanediyl, C₂-C₆alkenediyl, C₂-C₆alkaediyl, C₂-C₆alkanediyl, C₂-C₆alkanediyl, C₃-C₆cycloalkanediyl, C₃-C₆cycloalkenediyl or phenylene each optionally substituted by fluorine, chlorine or bromine ,
A² represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, in which A⁴ represents hydrogen, hydroxy, C₁-C₄-alkyl, C₁-C₄-alkoxy, Phenyl, C₁-C₄ alkylsulfonyl or phenylsulfonyl,
A² further represents C₁-C₆-alkanediyl, C₂-C₆-alkanediyl, C₂-C₆-azaalkenediyl, C₂-C₆-alkynediyl, C₂-C₆-alkynediyl, C₃-C₆-cycloalkanediyl, C₃-C₆-cycloalkenediyl or phenylene, each optionally substituted by fluorine, chlorine or bromine ,
A³ represents hydrogen, with the proviso that in this case A¹ and / or A² do not represent a single bond,
A³ further for hydroxy, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for each optionally substituted by fluorine, chlorine or C₁-C₄-alkoxy-substituted alkyl , Alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy- (thio) phosphoryl each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl optionally substituted by fluorine or chlorine, Alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, each optionally by fluorine, chlorine, cyano, carboxy, C₁-C₄-alkyl and / or C₁-C₄-alkoxy-carbonyl substituted cycloalkyl, cycloalkyl oxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidene amino, cycloalkyloxycarbonyl or cycloalkylalkoxy carbonyl, each with 3 bi s 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄- Alkyloxy, C₁-C₄-halogen alkyloxy and / or C₁-C₄-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alk oxy, phenyloxycarbonyl or phenyl-C₁-C₄-alkoxycarbonyl ,
A³ furthermore for in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, tri-pyridinyl, pyridinyl, pyriminyl, pyriminyl, pyriminyl, pyriminyl C₄-alkyl, furyl-C₁-C₄-alkyl, thienyl-C₁-C₄-alkyl, oxazolyl-C₁-C₄-alkyl, isoxazolyl-C₁-C₄-alkyl, thiazolyl-C₁-C₄-alkyl, pyridinyl-C₁-C₄ -alkyl, pyrimidinyl-C₁-C₄-alkyl, pyrazolylmeth oxy, furylmethoxy, represents perhydropyranylmethoxy or pyridylmethoxy, and
R⁷ represents hydrogen, fluorine or chlorine,
or two adjacent residues - R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶ or R⁶ and R⁷ - together represent one of the following groups -Q³-CQ⁴-, -Q³-CQ⁴-Q⁵-, -Q³-C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -CQ⁴-, -C (R⁸, R⁹) -Q³-CQ⁴-, -Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -, -Q³ -C (R⁸, R⁹) -C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-, -Q³-C (R⁸) = C (R⁸) -, -C (R⁸) -C (R⁸) -CQ⁴-, -Q³-C (R⁸, R⁹) -CQ⁴-, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-, -C (R⁸) = N -, -Q³-CQ⁴-C (R⁸, R⁹) -, -Q³-CQ⁴-N (R¹⁰) -, -Q³-C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹ ) -Q³-CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴- N (R¹⁰) -, -C (R⁸) = C (R⁸) -N (R¹⁰) -, -C (R⁸) = C (R⁸) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) - CQ⁴-N (R¹⁰) -, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸) = NN (R¹⁰) -, -Q³-CQ⁴-C (R⁸, R⁹) -N (R¹⁰) -, Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) - whereby
Q³, Q⁴ and Q⁵ are the same or different and each represents oxygen or sulfur,
R⁵ and R⁹ are the same or different and individually represent hydrogen, fluorine, chlorine, bromine or C₁-C₄-alkyl or together represent C₂-C₅-alkanediyl, and
R¹⁰ for hydrogen, hydroxy, optionally substituted by cyano, fluorine, chlorine, C₁-C₄-alkoxy, C₁-C₄-alkyl-car bonyl or C₁-C₄-alkoxy-carbonyl alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl, each with 1 up to 6 carbon atoms in the alkyl groups, each for alkenyl or alkynyl optionally substituted by fluorine, chlorine or bromine or alkynyl each having 2 to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by fluorine, chlorine, bromine or C₁-C₄alkyl, each having 3 to 6 carbon atoms in the cyclo alkyl groups and optionally 1 to 3 atoms in the alkyl group, for alkoxy or alkenyloxy each optionally substituted by fluorine and / or chlorine, each having up to 6 carbon atoms, or for each optionally by cyano, fluorine, chlorine, C₁-C₄ -Alkyl, C₁-C₄-haloalkyl, C₁-C₄-alk oxy or C₁-C₄-haloalkoxy substituted benzyl or benzyloxy. 3. N-aryl nitrogen heterocycles of the general formula (I) according to claim 1, characterized in that
Q¹ represents oxygen or sulfur,
Q² represents oxygen or sulfur,
R¹ for cyano, formyl, each for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine, chlorine, cyano, carboxy, methoxy or ethoxy, for each optionally by Fluorine or chlorine-substituted propenyl, butenyl, propynyl or butynyl, each represents acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or ethylsulfonyl optionally substituted by fluorine or chlorine, or cyclopropyl optionally substituted by fluorine or chlorine,
R² for amino, cyano, formyl, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylamino, each optionally substituted by fluorine, chlorine, cyano, carboxy, methoxy or ethoxy, Ethyl amino, n- or i-propylamino, dimethylamino or diethylamino, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine or chlorine, for acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or ethylsulfonyl, each optionally substituted by fluorine or chlorine , or represents cyclo propyl optionally substituted by fluorine or chlorine, and
Ar represents the substituted, monocyclic or bicyclic aryl or heteroaryl group defined below, wherein
R³ represents hydrogen, fluorine or chlorine,
R⁴ represents hydrogen, fluorine or chlorine or
R⁵ represents cyano, thiocarbamoyl, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy,
R⁶ represents the following grouping, -A¹-A²-A³in which
A¹ is a single bond, oxygen is sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, where A⁴ is hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy, Ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,
A¹ further 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, propene-1,3-diyl, ethyne-1,2-diyl or propyne-1,3-diyl,
A² represents a single bond, represents oxygen, sulfur, -SO-, -SO₂-, -CO- or the grouping -N-A⁴-, wherein A⁴ represents hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, methoxy , Ethoxy, n- or i-propoxy, methylsulfonyl, ethyl sulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A² 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, propene-1,3-diyl, ethyne-1,2-diyl or propyne-1,3-diyl,
A³ represents hydrogen, with the proviso that in this case A¹ and / or A² do not represent a single bond,
A³ furthermore for hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n- which is optionally substituted by fluorine, chlorine, methoxy or ethoxy , 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-Propyl sulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, dimethoxyphosphoryl , Diethoxyphosphoryl or Dipropoxyphosphoryl, Diisopropoxyphosphoryl, each for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylidenamino, propenyloxycarbonyl, optionally substituted by fluorine or chlorine tenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, for each cyclopropyl, cyclobutyl, optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxy carbonyl, Cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyl oxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclo-propyl methoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclo hexylmethoxy, cyclopentylhexyloxyoxyoxy, cyclopentylhexyloxyoxycarbonyl, cyclohexyl methoxycarbonyl, cycloentyl methoxycarbonyl, cyclohexyl methoxy carbonyl, cyclo pentyl methoxy carbonyl substituted by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromoxy, trifluoromethoxy, methoxycarbonyl and / or eth oxycarbonyl Phenyl, phenyloxy, benzyl, phenylethyl, Benzyloxy, phenyloxycarbonyl, benzyloxy carbonyl,
A³ furthermore for each optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethylazylylmethyl, furyl Isoxazolylmethyl, thiazolylmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy,
R⁷ represents hydrogen, fluorine or chlorine,
or two adjacent residues - R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶ or R⁶ and R⁷ - together represent one of the following groups -Q³-CQ⁴-, -Q³-CQ⁴-Q⁵-, -Q³-C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -CQ⁴-, -C (R⁸, R⁹) -Q³-CQ⁴-, -Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -, -Q³ -C (R⁸, R⁹) -C (R⁸, R⁹) -Q⁵-, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-, -Q³-C (R⁸) = C (R⁸) -, -C (R⁸) = C (R⁸) -CQ⁴-, -Q³-C (R⁸, R⁹) -CQ⁴-, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-, -C (R⁸) = N -, -Q³-CQ⁴-C (R⁸, R⁹) -, -Q³-CQ⁴-N (R¹⁰) -, -Q³-C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹ ) -Q³-CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -N (R¹⁰) -, -C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴- N (R¹⁰) -, -C (R⁸) = C (R⁸) -N (R¹⁰) -, -C (R⁸) = C (R⁸) -CQ⁴-N (R¹⁰) -, -C (R⁸, R⁹) - CQ⁴-N (R¹⁰) -, -N (R¹⁰) -C (R⁸; R⁹) -CQ⁴-N (R¹⁰) -, -C (R⁸) = NN (R¹⁰) -, -Q³-CQ⁴-C (R⁸, R⁹) -N (R¹⁰) -, -Q³-C (R⁸, R⁹) -C (R⁸, R⁹) -CQ⁴-N (R¹⁰) -wher
Q³, Q⁴ and Q⁵ are the same or different and each represents oxygen or sulfur,
R⁵ and R⁹ are the same or different and individually represent hydrogen, fluorine, chlorine, methyl or ethyl or together represent ethane-1,2-diyl (dimethylene), and
R¹⁰ for hydrogen, hydroxy, optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl sub-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, each optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, Cyclopentylmethyl or cyclohexylmethyl, for methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy or butenyloxy, each optionally substituted by fluorine and / or chlorine, or for each optionally by cyano, fluorine, Chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, di fluoromethoxy or trifluoromethoxy substituted benzyl or benzyloxy. 4. Process for the preparation of N-aryl nitrogen heterocycles of the general formula (I) in which R¹, R², Q¹, Q² and Ar have the meaning given in Claim 1, characterized in that

• (a) (Thio) urazole derivatives of the general formula (II) in which
  Q¹, Q² and Ar have the meanings given above,
  A¹ is hydrogen or has the meanings given for R¹ Be and
  A² stands for hydrogen or has the meanings given above for R²,
  however, at least one of the groups A¹ or A² is hydrogen,
  with alkylating agents of the general formulas (IIIa) or (IIIb) R¹-X (IIIa) R²-X (IIIb) in which
  R¹ and R² have the meanings given above and
  X represents halogen, -O-SO₂-O-R¹ or -O-SO₂-O-R²,
  if appropriate in the presence of a reaction auxiliary and, if appropriate, in the presence of a diluent and, if appropriate, subsequently carry out electrophilic or nucleophilic substitution reactions as part of the definition of substituents,
  or that one
• (b) (Thio) urazoles of the general formula (IV) in which
  Q¹, Q², R¹ and R² have the meanings given above,
  with halogen arenes of the general formula (V) Ar-X (V) in which
  Ar has the meaning given above and
  X represents halogen,
  if appropriate in the presence of a reaction auxiliary and, if appropriate, in the presence of a diluent and, if appropriate, subsequently carry out electrophilic or nucleophilic substitution reactions as part of the definition of substituents,
  or that one
• (c) aryl (thio) semicarbazides of the general formula (VI) in which
  Ar, Q¹, R¹ and R² have the meanings given above,
  with (thio) phosgene, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and if appropriate subsequently carrying out electrophilic or nucleophilic substitution reactions as part of the definition of substituents in the customary manner.

5. Herbicides and / or insecticidal agents, characterized by a content on at least one N-aryl nitrogen heterocycle of the general formula (I) according to claims 1 to 4. 6. methods for controlling unwanted plants and / or insects, characterized in that N-aryl nitrogen heterocycles of gen my formula (I) according to claims 1 to 4 on undesired plants zen and / or insects and / or their habitats. 7. Use of N-aryl nitrogen heterocycles of the general formula (I) according to claims 1 to 4 for combating undesirable plants zen and / or insects. 8. Process for the preparation of herbicidal and / or insecticidal agents, characterized in that N-aryl nitrogen heterocycles of gen my formula (I) according to claims 1 to 4 with extenders and / or surface-active substances mixed.