DE19936360A1 - Substituted arylhydrazone carboxylic acid derivatives - Google Patents

Abstract

The invention relates to novel, substituted arylhydrazone carboxylic acid derivatives of general formula (I), wherein R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7> and R<8> have the meaning defined in the description. The invention further relates to a method for producing said derivatives and to their use as herbicides.

Description

The invention relates to new substituted arylhydrazone carboxylic acid derivatives, a Ver drive to their manufacture and their use as herbicides.

Arylhydrazone carboxylic acid derivatives have so far not been used as biologically active compounds gene became known.

There have now been the new substituted arylhydrazone carboxylic acid derivatives of the general formula (I),

in which
R ^{1 represents} hydrogen, nitro, cyano or halogen,
R ^{2 represents} nitro, cyano, thiocarbamoyl, halogen or optionally substituted alkyl or alkoxy,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, alkyl, alkenyl, Alkynyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
A ¹ furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A ^{2 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, alkyl, alkoxy, Aryl, alkylsulfonyl or arylsulfonyl,
A ² furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A ³ for hydrogen, hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, which are optionally substituted by halogen or alkoxy, Dialkylamino, alkoxycarbonyl or dialkoxy (thio) - phosphoryl, for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxy carbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl, each optionally substituted by halogen, each optionally substituted by halogen, cyano, carboxy, alkyl and / or Alkoxy-carbonyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyl oxycarbonyl or cycloalkylalkoxycarbonyl, or for each optionally by nitro, cyano, carboxy, halogen, alkyl, haloalkyl, alkyloxy, haloalkyloxy and / or alkoxycarbonyl substituted aryl, aryloxy , Aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxy approx rbonyl stands,
A ³ also represents in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, tridinyl or pyrimidinyl, pyrimidinyl
however, A ¹ and A ^{2 are} not both simultaneously one of the radicals O, S, -SO- or -SO ₂ -,
or the two radicals R ² and R ³ together represent one of the groups below
-Q ¹ -CQ ² -, -Q ¹ -CQ ² -Q ¹ -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-Q ¹ -C (R ⁹ ) = C (R ⁹ ) -, -C (R ⁹ ) = C (R ⁹ ) -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² - ,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -, -C (R ⁹ ) = N-, -Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -CQ ² -N (R ¹¹ ) -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = C (R ⁹ ) -N (R ¹¹ ) -,
-C (R ⁹ ) = C (R ⁹ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = NN (R ¹¹ ) -,
-Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -, Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -
in which
Q ¹ and Q ^{2 are the} same or different and each represents their oxygen or sulfur,
R ⁹ and R ^{10 are the} same or different and are individually their hydrogen, halogen or alkyl or together are their alkanediyl, and
R ^{11 represents} hydrogen or represents optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl or benzyl,
R ^{4 represents} hydrogen or optionally substituted alkyl,
R ^{5 represents} hydrogen, cyano, halogen or optionally substituted alkyl,
R ^{6 represents} optionally substituted alkyl,
R ^{7 represents} hydrogen, halogen, or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy or alkynylthio, and
R ^{8 represents} hydrogen or optionally substituted alkyl,
found.

The general formula (I) excludes the possible E and Z configurations isomers with a.

Saturated or unsaturated hydrocarbon radicals, such as alkyl, alkenyl or Alkynyl, so far - also in connection with heteroatoms, such as in alkoxy possible straight or branched.

Preferred substituents of the formulas given above and below listed residues are explained below.

R ¹ preferably represents hydrogen, nitro, cyano or halogen.

R ² preferably represents nitro, cyano, thiocarbamoyl, halogen or alkyl or alkoxy each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having 1 to 4 carbon atoms.

R ³ preferably represents the group -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, C ₁ -C _6- alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -alkoxy, phenyl, C ₁ -C ₆ -alkylsulfonyl or phenylsulfonyl,
A ¹ furthermore for C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkanediyl, C ₂ -C ₆ -azaalkenediyl, C ₂ -C ₆ -alkanediyl, C ₂ -C ₆ -alkanediyl, C ₃ -C in each case optionally substituted by fluorine and / or chlorine _6- cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,
A ^{2 represents} a single bond, represents O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, C ₁ -C _6- alkyl, C ₁ -C ₆ -alkoxy, phenyl, C ₁ -C ₆ -alkylsulfonyl or phenylsulfonyl,
A ² further for C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkanediyl, C ₂ -C ₆ -azaalkenediyl, C ₂ -C ₆ -alkanediyl, C ₂ -C ₆ -alkanediyl, C ₃ -C in each case optionally substituted by fluorine and / or chlorine _6- cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,
A ³ for hydrogen, hydroxy, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for C in each case optionally substituted by fluorine, chlorine or C ₁ -C ₆ alkoxy ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkyl thio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylamino, di- (C ₁ -C ₄ -alkyl) -amino, C ₁ -C ₆ -alkoxy-carbonyl or di- (C ₁ -C ₆ -alkoxy) - (thio) phosphoryl, for each optionally substituted by fluorine and / or chlorine ₂ -C ₆ alkenyl, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ alkenyl amino, C ₂ -C ₆ -Alkylidenamino, C ₂ -C ₆ alkenyloxycarbonyl, C ₂ -C ₆ - alkynyl, C ₂ -C ₆ -alkynyloxy, C ₂ -C ₆ -alkynylamino or C ₂ -C ₆ -alkynyl oxy-carbonyl, each optionally with fluorine, chlorine, cyano, carboxy, C ₁ -C ₄ -alkyl and / or C ₁ - C ₄ -alkoxy-carbonyl substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyloxy, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ -alkoxy, C ₃ -C ₆ -cycloalkyloxycarbonyl or C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkoxy-carbonyl, or for any given case by nitro, cyano, carboxy, fluorine, chlorine, Bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkyloxy, C ₁ -C ₄ haloalkyloxy and / or C ₁ -C ₄ alkoxycarbonyl substituted phenyl, phenyloxy, Phenyl-C ₁ -C ₄ -alkyl, phenyl-C ₁ -C ₄ -alkoxy, phenyloxy-carbonyl or phenyl-C ₁ -C ₄ - alkoxy-carbonyl,
A ³ furthermore represents in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridinyl, pyridolyl, pyridinyl
however, A ¹ and A ^{2 are} not both each one of the radicals O, S, -SO- or -SO ₂ -.

R ² and R ³ preferably also together represent one of the groupings below
-Q ¹ -CQ ² -, -Q ¹ -CQ ² -Q ¹ -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-Q ¹ -C (R ⁹ ) = C (R ⁹ ) -, -C (R ⁹ ) = C (R ⁹ ) -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² - ,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -, -C (R ⁹ ) = N-, -Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -CQ ² -N (R ¹¹ ) -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = C (R ⁹ ) -N (R ¹¹ ) -,
-C (R ⁹ ) = C (R ⁹ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = NN (R ¹¹ ) -,
-Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -, Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -
in which
Q ¹ and Q ^{2 are the} same or different and each represents oxygen or sulfur,
R ⁹ and R ^{10 are the} same or different and individually represent hydrogen, halogen or C ₁ -C ₄ alkyl or together represent C ₂ -C ₅ alkanediyl, and
R ¹¹ for hydrogen, for each optionally substituted by cyano, fluorine, chlorine or C ₁ -C ₄ -alkoxy-substituted alkyl, alkylcarbonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, for each optionally substituted by fluorine, chlorine or bromine or alkynyl, each having 2 to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl, each optionally substituted by fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 atoms in the alkyl part, or for benzyl optionally substituted by cyano, fluorine, chlorine, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy.

R ⁴ preferably represents hydrogen or alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy.

R ⁵ preferably represents hydrogen, cyano, halogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy.

R ⁶ preferably represents alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy.

R ⁷ preferably represents hydrogen, halogen, in each case alkyl, alkoxy, alkylthio, alkylamino, dialkylamino each optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, or each in each case optionally by halogen substituted alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy or alkynylthio each having 2 to 6 carbon atoms.

R ⁸ preferably represents hydrogen or alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy.

R ¹ particularly preferably represents hydrogen, cyano, fluorine or chlorine.

R ² particularly preferably represents cyano, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine, chlorine, methoxy or ethoxy.

R ³ particularly preferably represents the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, represents O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, propenyl, butenyl, propynyl, butinyl, methoxy, ethoxy, n- or i-propoxy, phenyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, or phenylsulfonyl,
A ¹ furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, methyl, ethyl, n- or i-propyl, methoxy , Ethoxy, n- or i-propoxy, methyl sulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A ² furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ³ for hydrogen, hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy , i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n- , i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-Propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, for each optionally fluorine or chlorine substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxy carbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamine o, propynyloxycarbonyl or butynyloxycarbonyl, for each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy , Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclo-propylmethoxy, Cyclobutylmethoxy, Cyclo pentylmethoxy, Cyclohexylmethoxy, Cyclopentylidenamino, Cyclo hexylidenamino, Cyclopentyloxycarbonyl, Cyclohexyloxycarbonyl, Cyclopentylmethoxy, cyclo, cyclo or carbonyl, cyclo or carbonyl, cyclo or carbonyl, cyclo or carbonyl, cyclo, or cyclo Methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl or benzyloxycarbonyl,
A ³ furthermore represents dioxolanyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl,
however, A ¹ and A ^{2 are} not both each one of the radicals O, S, -SO- or -SO ₂ -.

R ² and R ³ are particularly preferably also together for one of the groupings below
-Q ¹ -CQ ² -, -Q ¹ -CQ ² -Q ¹ -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-Q ¹ -C (R ⁹ ) = C (R ⁹ ) -, -C (R ⁹ ) = C (R ⁹ ) -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² - ,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -, -C (R ⁹ ) = N-, -Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -CQ ² -N (R ¹¹ ) -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = C (R ⁹ ) -N (R ¹¹ ) -,
-C (R ⁹ ) = C (R ⁹ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = NN (R ¹¹ ) -,
-Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -, Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -
in which
Q ¹ and Q ^{2 are the} same or different and each represents oxygen or sulfur,
R ⁹ and R ^{10 are the} same or different and individually represent hydrogen, fluorine, chlorine, methyl or ethyl or together represent ethane-1,2-diyl (di methylene), and
R ^{11 is} hydrogen, for methyl, ethyl, n- or i-propyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for propenyl, butenyl, each optionally substituted by fluorine or chlorine, Propynyl or butynyl, each represents cyclopropyl or cyclopropylmethyl optionally substituted by fluorine, chlorine, methyl or ethyl, or represents benzyl each optionally substituted by cyano, fluorine, chlorine, methyl, ethyl, methoxy or ethoxy.

R ⁴ particularly preferably represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i- or s-butyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy.

R ⁵ particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or optionally substituted by fluorine, chlorine, methoxy or ethoxy t-butyl.

R ⁶ particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy.

R ⁷ particularly preferably represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, n-, i-, s- or t- which is optionally substituted by fluorine, chlorine, methoxy or ethoxy. Butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethyl amino or dipropylamino, or for ethenyl, propenyl, butenyl, propenyloxy which are optionally substituted by fluorine, chlorine or bromine, Butenyloxy, propenylthio, butenylthio, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylthio or butynylthio.

R ⁸ particularly preferably represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy.

R ¹ very particularly preferably represents hydrogen, fluorine or chlorine.

R ² very particularly preferably represents cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl.

R ³ very particularly preferably represents the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, methyl, ethyl, propenyl, Butenyl, propynyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl,
A ¹ furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, methyl, ethyl, methylsulfonyl, ethylsulfonyl, n- or i Propylsulfonyl,
A ² furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ³ for hydrogen, hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy , 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-, 1-, s- or t-butylthio, methylsulfinyl, ethylsullinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-Propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, for each optionally fluorine or chlorine substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxy carbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamine o, propynyloxycarbonyl or butynyloxycarbonyl, for each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy , Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclo-propylmethoxy, Cyclobutylmethoxy, Cyclo pentylmethoxy, Cyclohexylmethoxy, Cyclopentylidenamino, Cyclo hexylidenamino, Cyclopentyloxycarbonyl, Cyclohexyloxycarbonyl, Cyclopentylmethoxy, cyclo, cyclo or carbonyl, cyclo or carbonyl, cyclo or carbonyl, cyclo or carbonyl, cyclo, or cyclo Methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl or benzyloxycarbonyl,
A ³ furthermore represents furyl, tetrahydrofuryl, thienyl, dioxolanyl, oxazolyl, isoxazolyl or pyridinyl,
however, A ¹ and A ^{2 are} not both each one of the radicals O, S, -SO- or -SO ₂ -.

R ² and R ³ very particularly preferably also stand together for one of the groups below
-Q ¹ -CQ ² -, -Q ¹ -CQ ² -Q ¹ -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-Q ¹ -C (R ⁹ ) = C (R ⁹ ) -, -C (R ⁹ ) = C (R ⁹ ) -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² - ,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -, -C (R ⁹ ) = N-, -Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -CQ ² -N (R ¹¹ ) -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = C (R ⁹ ) -N (R ¹¹ ) -,
-C (R ⁹ ) = C (R ⁹ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = NN (R ¹¹ ) -,
-Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -, Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -
in which
Q ¹ and Q ^{2 are the} same or different and each represents oxygen or sulfur,
R ⁹ and R ^{10 are the} same or different and individually represent hydrogen, fluorine, chlorine, methyl or ethyl or together represent ethane-1,2-diyl (di methylene), and
R ^{11 represents} hydrogen, in each case optionally substituted by fluorine, methoxy or ethoxy-substituted methyl or ethyl, or for propenyl, butenyl, propynyl or butynyl which is optionally substituted by fluorine or chlorine.

R ⁴ very particularly preferably represents hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine.

R ⁵ very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine.

R ⁶ very particularly preferably represents methyl or ethyl which is optionally substituted by fluorine or chlorine.

R ⁷ very particularly preferably represents hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine.

R ⁸ very particularly preferably represents hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy.

R ¹ most preferably represents fluorine.

R ² most preferably represents cyano or thiocarbonyl.

R ³ most preferably represents methoxy or -C ₂ C ₅ SO ₂ NH-.

R ⁴ most preferably represents hydrogen.

R ⁵ most preferably represents hydrogen.

R ⁶ most preferably represents methyl which is optionally substituted by fluorine or chlorine.

R ⁷ most preferably represents hydrogen.

R ⁸ most preferably represents methyl, ethyl, n- or i-propyl.

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

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

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

Most preferred according to the invention are those compounds of the formula (I), in which a combination of the above is most preferred listed meanings is present.

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

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

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

Ar stands for the grouping

in general Formula (I)

Group 1

Ar has, for example, the meanings listed below:
2,4,5-trichlorophenyl, 2,4-dichloro-5-fluorophenyl, 2-chloro-4,5-difluorophenyl, 4-chloro-2,5-difluorophenyl, 5-chloro 2,4-difluorophenyl, 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, 2-chloro 4-cyano-5-methylphenyl, 2,5-dichloro-4-trifluoromethylphenyl, 2,5-dichloro-4-nitrophenyl, 2,4-dichloro-5-methoxyphenyl, 2,4-dichloro -5-ethoxy-phenyl, 2,4-dichloro-5-n-propoxy-phenyl, 2,4-dichloro-5-i-propoxy-phenyl, 4-chloro-2-fluoro-5-methoxy-phenyl, 4 -Chlor-2-fluoro-5-ethoxy-phenyl, 4-chloro-2-fluoro-5-n-propoxy-phenyl, 4-chloro-2-fluoro-5-i-propoxy-phenyl, 2-fluoro-4 -cyano-5-methylphenyl, 2-chloro-4-cyano-5-trifluoromethylphenyl, 4-fluoro-3-trifluoromethylphenyl, 2-fluoro-4-cyano-5-trifluoromethylphenyl, 2.5- Difluoro-4-thiocarbamoyl-phenyl, 2-chloro-4-fluoro-5-i-propoxy-phenyl, 2-fluoro-4-cyano-5-methoxy-phenyl, 2-fluoro-4-cyano-5-i- propoxy-phenyl, 2-C hlor-4-cyano-5- (2-propynyloxy) phenyl, 2-fluoro-4-cyano-5- (1-methyl-2-propynyloxy) phenyl, 2-chloro-4-thiocarbamoyl-5-i- propoxyphenyl, 2-fluoro-4-cyano-5- (2-propenyloxy) phenyl, 2-fluoro-4-chloro-5- (2-propenyl oxy) phenyl, 2-chloro-4-cyano-5 -methylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-ethylsulfonylamino-phenyl, 2-chloro-4-trifluoromethyl-5-ethylsulfonylamino-phenyl, 2-fluoro-4-trifluoromethyl-5-ethylsulfonylamino-phenyl, 2-fluorine -4-thiocarbamoyl-5-methylsulfonylphenyl, 2-chloro-4-cyano-5-ethylsulfonylamino-phenyl, 2-chloro-4-nitro-5-ethoxyphenyl, 2-fluoro-4-nitro-5-ethoxy -phenyl, 2-fluoro-4-cyano-5-cyclopropylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-i-propylsulfonylamino-phenyl, 2-chloro-4-thiocarbamoyl-5-ethylsulfonylamino-phenyl, 2- Fluoro-4-cyano-5-trifluoromethylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-phenylsulfonylamino-phenyl, 2-fluoro-4-cyano-5-t-butylsulfonylamino-phenyl, 2-chloro-4 -cyano-5-methoxycarbonyl-phenyl, 2-fluoro-4-cyano-5-ethoxycarbonyl-phenyl, 2-fluoro-4-thiocarbamoyl-5 me thoxycarbonylphenyl, 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-thiocarbamoyl-5-methoxycarbonylmethyl-phenyl, 2-chloro-4-cyano-5- (N-methyl-ethylsulfonylamino) -phenyl, 2-chloro-4-cyano- 5-i-propoxycarbonylphenyl, 2-fluoro-4-cyano-5- (bis-ethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (N-methylsulfonylethylsulfonylamino) phenyl, 2- Fluoro-4-cyano-5- (1-methoxycarbonyl-ethoxy) phenyl, 2-fluoro-4-cyano-5-cyclopropyloxy-phenyl, 2-chloro-4-cyano-5-dimethylamino-phenyl, 2-fluoro- 4-cyano-5-tetrahydrofurylmethoxyphenyl, 2-fluoro-4-cyano-5-aminophenyl, 2-fluoro-4-cyano-5-methylaminocarbonylphenyl, 2-fluoro-4-cyano-5-methylsulfonyloxy- phenyl, 2-chloro-4-cyano-5-difluoro methoxy-phenyl, 2-fluoro-4-cyano-5-ethoxycarbonylmethoxy-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-chloro-5-hydroxy-phenyl, 2-fluoro-4-chloro-5-nitro-phenyl, 2-fluoro-4-chloro-5-aminophenyl, 2 -Fluoro-4-cyano-5-nitro-phenyl, 2-fluoro-4-cyano-5-aminophenyl, 2-fluoro-4-cyano-5-formylamino-phenyl, 2-chloro-4-cyano-5 -ethoxycarbonyl oxy-phenyl, 2-chloro-4-cyano-5-hydroxy-phenyl, 2-fluoro-4-cyano-5- (N, N-diacetyl amino) phenyl, 2-fluoro-4-cyano-5 -acetylamino-phenyl, 2-fluoro-4-cyano-5-tetra hydrofuryloxy-phenyl, 2-fluoro-4-cyano-5-ureido-phenyl, 2-fluoro-4-cyano-5-dimethoxymethyleneamino-phenyl, 2- Chloro-4-cyano-5-ethoxymethyleneaminophenyl, 2-fluoro-4-cyano-5- (2-chloroethoxycarbonyloxy) phenyl, 2-fluoro-4-cyano-5- (2-methoxycarbonyl-ethyl) - phenyl, 2-chloro-4-cyano-5- (2-carboxy-2-chloro-ethyl) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-methoxycarbonyl-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-methylethyl) phenyl, 2-chloro-4-cyano-5- (2-chloro-2-i-propoxy carbonyl-ethyl) -phenyl, 2,4-dichloro-5- (2-methoxycarbonyl-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-chloroethyl) phenyl, 2-fluorine -4-cyano-5- (2-ethoxycarbonyl-ethenyl) phenyl, 2-fluoro-4-cyano-5- (2-chloro-2-cyclopropylamino carbonyl-ethyl) phenyl, 2-fluoro-4-cyano- 5- (2-chloro-2-dimethylaminocarbonyl-ethyl) phenyl, 2-chloro-4-cyano-5- (2-chloro-2-ethylsulfonylaminocarbonyl-ethyl) phenyl, 2-fluoro-4-chloro-5- (2-carboxy-ethenyl) phenyl, 2-fluoro-4-thiocarbamoyl-5- (2-ethylaminocarbonyl-ethenyl) phenyl, 2-fluoro-4-cyano-5- (l-ethoxycarbonyl-ethyl) phenyl, 2-chloro-4-cyano-5- (l-ethoxycarbonylethyl) phenyl, 2-chloro-4-cyano-5-carboxyphenyl, 2-fluoro-4-chloro-5- (l-ethoxycarbonyl-ethyl ) -phenyl, 2-fluoro-4-chloro-5- (li-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-ch lor-5- (2-methoxyethoxy) phenyl, 2-fluoro-4-chloro-5-i-butoxyphenyl, 2-fluoro-4-cyano-5- (2-oxetanyloxy) phenyl, 2- Fluoro-4-cyano-5- (2-oxetanyloxycarbonyl methoxy) phenyl, 2-fluoro-4-cyano-5- (2-oxetanyloxy) phenyl, 3-fluoro-4-cyano-phenyl, 3-chloro-4 -cyano-phenyl, 2-chloro-4-cyano-5- (2-methoxy-ethoxy) -phenyl, 2-fluoro-4-cyano-5- (N-acetyl-N-methylsulfonyl-amino) -phenyl, 2 -Fluoro-4-chloro-5- (N-acetyl-N-methylsulfonyl-amino) -phenyl, 2-fluoro-4-cyano-5- (N-propionyl-N-methylsulfonyl-amino) -phenyl, 2- Fluoro-4-chloro-5- (N-propionyl-N-methylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (Ni-butyroyl-N-methylsulfonylamino) phenyl, 2-fluoro 4-chloro-5- (Ni-butyroyl-N-methylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (N-pivaloyl-N-methylsulfonylamino) phenyl, 2-fluoro-4- chloro-5- (N-pivaloyl-N-methyl sulfonylamino) phenyl, 2-fluoro-4-cyano-5- (N-benzoyl-N-methylsulfonylamino) phenyl, 2-fluoro-4-chloro -5- (N-benzoyl-N-methylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (N-4-methoxy-benzoyl-N-methylsulfonylamino) pheny 1,2-fluoro-4-chloro-5- (N-4-methoxy-benzoyl-N-methylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (2-oxetanyloxy) phenyl, 3- Fluoro-4-cyano-phenyl, 3-chloro-4-cyano-phenyl, 2-chloro-4-cyano-5- (2-methoxy-ethoxy) -phenyl, 2-fluoro-4-cyano-5- (N -acetyl-N-ethylsulfonylamino) phenyl, 2-fluoro-4-chloro-5- (N-acetyl-N-ethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (N-propionyl -N-ethylsulfonylamino) phenyl, 2-fluoro-4-chloro-5- (N-propionyl-N-ethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (Ni-butyroyl-N -ethyl sulfonyl-amino) -phenyl, 2-fluoro-4-chloro-5- (Ni-butyroyl-N-ethylsulfonyl-amino) -phenyl, 2-fluoro-4-cyano-5- (N-pivaloyl-N- ethylsulfonylamino) phenyl, 2-fluoro-4-chloro-5- (N-pivaloyl-N-ethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (N-benzoyl-N-ethylsulfonyl- amino) phenyl, 2-fluoro-4-chloro-5- (N-benzoyl-N-ethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (N-4-methoxy-benzoyl-N- ethylsulfonyl-amino) - phenyl, 2-fluoro-4-chloro-5- (N-4-methoxy-benzoyl-N-ethylsulfonyl-amino) -phenyl, 2-fluoro-4-thiocarbamoyl-5- (Na cetyl-N-ethylsulfonylamino) phenyl, 2-fluoro-4-thio carbamoyl-5- (N-propionyl-N-ethylsulfonylamino) phenyl, 2-fluoro-4-thio carbamoyl-5- (Ni butyroyl-N-ethylsulfonylamino) phenyl, 2-fluoro-4-thio carbamoyl-5- (N-benzoyl-N-ethylsulfonylamino) phenyl, 2-fluoro-4-cyano-5- (3-hydroxy -phenoxy) -phenyl, 2-fluoro-4-cyano-5- (3-methoxy-phenoxy) -phenyl, 2-fluoro-4-cyano-5- (3-ethoxycarbonyl-methoxy-phenoxy) -phenyl, 2- Fluoro-4-cyano-5- (3-propargyloxyphenoxy) phenyl, 2-fluoro-4-cyano-5- (4-hydroxyphenoxy) phenyl, 2-fluoro-4-cyano-5- (4th -methoxy-phenoxy) -phenyl, 2-fluoro-4-cyano-5- (4-ethoxy carbonyl-methoxy-phenoxy) -phenyl, 2-fluoro-4-cyano-5- (4-propargyloxy-phenoxy) phenyl , 2-fluoro-4-chloro-5- (2-hydroxyphenoxy) phenyl, 2-fluoro-4-chloro-5- (2-methoxyphenoxy) phenyl, 2-fluoro-4-chloro-5 - (2-ethoxycarbonyl-methoxy-phenoxy) phenyl, 2-fluoro-4-chloro-5- (2-propargyloxy-phenoxy) -phenyl, 2-fluoro-4-chloro-5- (3-hydroxyphenoxy) -phenyl, 2-fluoro-4-chloro-5- (3-methoxy-phenoxy) -phenyl, 2-fluoro-4-chloro-5- (3-ethoxycarbonyl-met hoxy-phenoxy) phenyl, 2-fluoro-4-chloro-5- (3-propargyloxy-phenoxy) -phenyl, 2-fluoro-4-chloro-5- (4-hydroxy-phenoxy) phenyl, 2-fluoro -4-chloro-5- (4-methoxy-phenoxy) phenyl, 2-fluoro-4-chloro-5- (4-ethoxycarbonyl-methoxy-phenoxy) phenyl, 2-fluoro-4-chloro-5- ( 4-propargyloxyphenoxy) phenyl, 2-fluoro-4-chloro-5- (2-hydroxyphenoxy) phenyl, 2-fluoro-4-chloro-5- (2-methoxy phenoxy) phenyl, 2- Fluoro-4-chloro-5- (2-ethoxycarbonyl-methoxy-phenoxy) phenyl, 2-fluoro-4-chloro-5- (2-propargyloxy-phenoxy) phenyl.

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.

The new substituted arylhydrazone carboxylic acid derivatives of the general formula (I) have interesting biological properties. They stand out particularly special due to strong herbicidal activity.

You get the new substituted arylhydrazone carboxylic acid derivatives of the general formula (I), if one
Arylhydrazones of the general formula (II)

in which
R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^{6 have} the meaning given above
With
Phosphonecarboxylic acid derivatives of the general formula (III)

in which
R ⁷ and R ^{8 have} the meaning given above and
R ¹² and R ¹³ each represent alkyl,
in the presence of a basic reaction auxiliary and in the presence of a diluent.

If, for example, 2,5-difluoro-4- [2- (3,3,3-trifluoro-2-oxo-propylidene) - hydrazino] -benzonitrile and 2- (dimethoxyphosphoryl) -acetic acid methyl ester are used as starting materials, then the The course of the reaction in the process according to the invention can be outlined by the following formula:

Formula (II) provides a general definition of the arylhydrazones to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (II), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ preferably or in particular have those meanings which have been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention preferably or as particularly preferred for R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ .

The starting materials of the general formula (II) are known and / or can be according to known processes can be produced (cf. WO-A-97/07104, DE-A- 197 54 348).

The arylhydrazones of the general formula (II) are obtained if arylhydrazines of the general formula (IV)

in which
R ¹ , R ² and R ^{3 have} the meaning given above,
with α-dihalocarbonyl compounds of the general formula (V)

in which
R ⁵ and R ^{6 have} the meaning given above and
X represents halogen (especially chlorine or bromine),
optionally in the presence of a diluent, such as. B. water, and optionally in the presence of a reaction auxiliary such. B. sodium acetate, at temperatures between 0 ° C and 100 ° C (see. The preparation examples).

R ¹² and R ¹³ in the general formula (III) are preferably C ₁ -C ₈ -alkyl.

The phosphonecarboxylic acid esters of the general formula (III) are known synthesis chemicals.

The process according to the invention for the preparation of compounds of general Formula (I) is carried out in the presence of a basic reaction auxiliary. It come here generally the usual inorganic or organic bases or acid acceptors. These preferably include alkali metal or Alkaline earth metal amides, carbonates, hydrides, hydroxides or alkanolates, as in for example lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, lithium, sodium, potassium or calcium hydride, lithium, Sodium, potassium or calcium hydroxide, sodium or potassium methanolate,  -ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; continue too basic organic nitrogen compounds, such as trimethylamine, tri ethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0] - undec-7-en (DBU).

The process according to the invention for the preparation of the compounds of the general Formula (I) is carried out using a diluent. As Diluents come to carry out the method according to the invention especially inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated carbons Hydrogen, such as gasoline, benzene, toluene, xylene, chlorobenzene, di chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetra chlorinated carbon; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or Methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; Esters such as acetic acid methyl ester or ethyl acetate, and sulfoxides, such as dimethyl sulfoxide.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work at temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.

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

To carry out the process according to the invention, the starting materials in generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The Reaction is carried out in a suitable diluent in the presence of a basic reaction auxiliary and the reaction mixture is carried out in all agitated several hours at the required temperature. The on work is carried out according to customary methods (cf. games).

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

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

Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.  

Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

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

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

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

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

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient im impregnated natural and synthetic materials as well as very fine encapsulation in polymers 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 can be used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, and water.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic  and organic flours as well as granules from organic material such as sawdust, Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam Generating funds are possible: z. B. non-ionic and anionic emuls gators, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants come into question: z. B. lignin sulfite and Methyl cellulose.

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

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

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

Known herbicides are suitable for the mixtures, for example
Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin (-ethyl), benftiresate, bensulfuron (-methyl) Benzobicyclone, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlo methoxyazide, Chlo methoxyazide , Chlorimuron (-ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid, clopyra sulfuron (-mulam) methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, dialallate, dicamba, diclofop (-methyl) , Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Di methachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, di thiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulf uron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, fenobenzene ), Fentrazamide, Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone, Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumet sulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Fluprop acil, Flurpyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptol), Fluroxone, Fluroxone, Fluroxone (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imaz , Imazapyr, Imazaquin, Imazethapyr, Imazo sulfuron, Iodosulfuron (-methyl, -so dium), Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methobenzthiazuron, Metobenzthiazuron, Metobenzthiazuron, Metobenzuriazuron, Metobenzthiazuron, Metobenzuriazuron, Metobenzuriazuron, Metobenzthiazuron, Metobenzuriazuron Metosulam, Metoxuron, Metribuzin, Metsulftiron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop amide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxa diazon, Oxasulfuron, Oxazicfluomalinone, Oxazicfluomalone, Paraz , Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Primi sulftiron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosulfuronoxoxyethyl- , Pyributicarb, Pyridate, Pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thia fluamide, thiazopyr, thidiazimin, thifensulfuron, tri-carboxylate, tri-benzyl, tri-benzyl, tri-benzo, tri-benzo, tri-benzo, tri-benzo, tri-benzo, tri-benzo, tri-benzo Triasulfuron, tribenuron (-methyl), triclopyr, tri diphane, trifluralin and triflusulfuron.

A mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellants, plants nutrients and soil structure improvers are possible.

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

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

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

The manufacture and use of the active compounds according to the invention start out the following examples.

Manufacturing examples

example 1

2.2 g (10 mmol) of 2- (diethoxyphosphoryl) -acetic acid ethyl ester in 50 ml Tetrahydrofuran with 0.42 g (11 mmol) of 60% sodium hydride in paraffin and the mixture is stirred at 25 ° C for 30 minutes. After adding 2.9 g (10 mmol) 5-fluoro-2-methoxy-4- [2- (3,3,3-trifluoro-2-oxo-propylidene) hydrazino] benzo Nitrile, the reaction mixture is stirred for 12 hours at 25 ° C and then in water jet vacuum concentrated. The residue is stirred with water, with conc. Salt acidified, the crystalline product isolated by suction and from isopropanol recrystallized.

1.9 g (53% of theory) of 3 - {[2- (4-cyano-2-fluoro-5-methoxyphenyl) - hydrazono] -methyl} -4,4,4-trifluoro-2-butenoic acid ethyl ester of melting point 251 ° C.

Analogously to Example 1 and in accordance with the general description of the production process according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Table 1 below.

Table 1

Examples of the compounds of the formula (I)

Starting materials of formula (II)

Example (II-1)

30 g (370 mmol) of sodium acetate are placed in 200 ml of water. Under ice cooling, 25 g (93 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone are added dropwise and the Mixture is stirred for 30 minutes at room temperature (approx. 20 ° C). Subsequently 12 g (72 mmol) of 2,5-difluoro-4-cyano-phenylhydrazine are added and the mixture is stirred Reaction mixture at 40 ° C to 50 ° C for 2 hours. The precipitated product becomes cold filtered off with water and dried.

19 g (95.4% of theory) of 3,3,3-trifluoro-2-oxo-propanal-1- (2,5- difluoro-4-cyano-phenylhydrazone) with a melting point of 181 ° C.  

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 ge wanted concentration.

Seeds of the test plants are sown in normal soil. After 24 hours the soil is sprayed with the active ingredient preparation so that the desired one Amount of active ingredient is applied per unit area. The drug concentration in the spray liquor is chosen so that in 01198 00070 552 001000280000000200012000285910178700040 0002019936360 00004 01779ls in 1000 liters of water per hectare desired amount of active ingredient is applied.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

0% = no effect (like untreated control) 100% = total annihilation

In this test, for example, the compounds according to the preparation example show 1, 2, 3 and 4 with good tolerance to crops, such as. B. Maize and rapeseed, strong against weeds.  

Example B Post emergence test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5- 15 cm so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l water / ha the desired amounts of active ingredient are applied. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control)
100% = total annihilation

In this test, for example, the compounds according to the preparation example show 1, 2, 3 and 4 with good tolerance to crops, such as. B. Barley, strong action against weeds.

Claims (8)

1. Compounds of the general formula (I),
in which
R ^{1 represents} hydrogen, nitro, cyano or halogen,
R ^{2 represents} nitro, cyano, thiocarbamoyl, halogen or optionally substituted alkyl or alkoxy,
R ^{3 stands} for the grouping -A ¹ -A ² -A ³ , in which
A ^{1 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, alkyl, alkenyl, Alkynyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl,
A ¹ furthermore represents alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene which are optionally substituted by halogen,
A ^{2 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, alkyl, alkoxy, Aryl, alkyl sulfonyl or arylsulfonyl,
A ^{2 is} furthermore in each case optionally substituted by halogen-substituted alkanediyl, alkenediyl, azaalkenediyl, alkindiyl, cycloalkanediyl, cycloalkenediyl or phenylene,
A ³ for hydrogen, hydroxy, amino, cyano, isocyano, thio cyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, which are optionally substituted by halogen or alkoxy, Dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl, for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl, each optionally substituted by halogen, each optionally substituted by halogen, cyano, carboxy, alkyl and / or alkoxy -carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, or for aryl, aryloxy which is optionally substituted by nitro, cyano, carboxy, halogen, alkyl, haloalkyl, alkyloxy, haloalkyloxy and / or alkoxycarbonyl, Aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbo nyl stands,
A ³ also represents in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, tridinyl or pyrimidinyl, pyrimidinyl
however, A ¹ and A ² do not both simultaneously represent one of the radicals O, S, -SO- or -SO ₂ -,
or the two radicals R ² and R ³ together represent one of the groupings below
-Q ¹ -CQ ² -, -Q ¹ -CQ ² -Q ¹ -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-Q ¹ -C (R ⁹ ) = C (R ⁹ ) -, -C (R ⁹ ) = C (R ⁹ ) -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² - ,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -, -C (R ⁹ ) = N-, -Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -CQ ² -N (R ¹¹ ) -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = C (R ⁹ ) -N (R ¹¹ ) -,
-C (R ⁹ ) = C (R ⁹ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = NN (R ¹¹ ) -,
-Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -, Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -
in which
Q ¹ and Q ^{2 are the} same or different and each represents oxygen or sulfur,
R ⁹ and R ^{10 are the} same or different and individually represent hydrogen, halogen or alkyl or together represent alkanediyl, and
R ^{11 represents} hydrogen or represents optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl or benzyl,
R ^{4 represents} hydrogen or optionally substituted alkyl,
R ^{5 represents} hydrogen, cyano, halogen or optionally substituted alkyl,
R ^{6 represents} optionally substituted alkyl,
R ^{7 represents} hydrogen, halogen, or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy or alkynylthio, and
R ^{8 represents} hydrogen or optionally substituted alkyl. 2. Compounds according to claim 1, characterized in that
R ^{1 represents} hydrogen, nitro, cyano or halogen,
R ^{2 represents} nitro, cyano, thiocarbamoyl, halogen or, in each case optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy-substituted alkyl or alkoxy each having 1 to 4 carbon atoms,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, C ₁ -C _6- alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -alkoxy, phenyl, C ₁ -C ₆ -alkylsulfonyl or phenylsulfonyl,
A ¹ furthermore for C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ -azaalkenediyl, C ₂ -C ₆ -alkanediyl, C ₃ -C _6, each optionally substituted by fluorine and / or chlorine -Cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,
A ^{2 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ , -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, C ₁ -C ₆ -Alkyl, C ₁ -C ₆ -alkoxy, phenyl, C ₁ -C ₆ -alkylsulfonyl or phenylsulfonyl,
A ² furthermore for C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ -azaalkenediyl, C ₂ -C ₆ -alkanediyl, C ₃ -C ₆ each optionally substituted by fluorine and / or chlorine -Cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,
A ^{3 is} hydrogen, hydroxy, amino, cyano, isocyano, thio cyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for each C optionally substituted by fluorine, chlorine or C ₁ -C ₆ alkoxy ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, C ₁ -C ₆ alkylamino, di- ( C ₁ -C ₄ alkyl) - amino, C ₁ -C ₆ alkoxy-carbonyl or di- (C ₁ -C ₆ alkoxy) - (thio) - phosphoryl, for each C optionally substituted by fluorine and / or chlorine ₂ -C ₆ alkenyl, C ₂ -C ₆ alkenyloxy, C ₂ -C ₆ alkenylamino, C ₂ -C ₆ alkylidene amino, C ₂ -C ₆ alkenyloxy carbonyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ -alkynyloxy, C ₂ -C ₆ -alkynylamino or C ₂ -C ₆ -alkynyloxy-carbonyl, for each given if appropriate by fluorine, chlorine, cyano, carboxy, C ₁ -C ₄ -alkyl and / or C ₁ -C ₄ alkoxy-carbonyl substituted C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyloxy, C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl-C ₁ - C ₄ -alkoxy, C ₃ -C ₆ -cycloalkyloxycarbonyl or C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkoxycarbonyl, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkyl oxy, C ₁ -C ₄ haloalkyloxy and / or C ₁ -C ₄ alkoxycarbonyl substituted phenyl, phenyloxy, Phenyl-C ₁ -C ₄ -alkyl, phenyl-C ₁ -C ₄ -alkoxy, phenyloxy-carbonyl or phenyl-C ₁ -C ₄ -alkoxy carbonyl,
A ³ also represents in each case fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridinyl, pyridinyl
however, A ¹ and A ² do not both simultaneously represent one of the radicals O, S, -SO- or -SO ₂ -, or
R ² and R ³ together represent one of the following groups:
-Q ¹ -CQ ² -, -Q ¹ -CQ ² -Q ¹ -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -Q ¹ -,
-C (R ⁹ , R ¹⁰ ) -CQ ² -, -C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -Q ¹ -,
-C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-Q ¹ -C (R ⁹ ) = C (R ⁹ ) -, -C (R ⁹ ) = C (R ⁹ ) -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² - ,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -, -C (R ⁹ ) = N-, -Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -CQ ² -N (R ¹¹ ) -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = C (R ⁹ ) -N (R ¹¹ ) -,
-C (R ⁹ ) = C (R ⁹ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = NN (R ¹¹ ) -,
-Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -, Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² - N (R ¹¹ ) -
in which
Q ¹ and Q ^{2 are the} same or different and each represents oxygen or sulfur,
R ⁹ and R ^{10 are the} same or different and individually represent hydrogen, halogen or C ₁ -C ₄ alkyl or together represent C ₂ -C ₅ alkanediyl, and
R ¹¹ for hydrogen, for alkyl, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by cyano, fluorine, chlorine or C ₁ -C ₄ -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl optionally substituted by fluorine, chlorine or bromine or alkynyl, each having 2 to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl, each optionally substituted by fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and, if appropriate, 1 to 3 atoms in Alkyl part, or represents benzyl optionally substituted by cyano, fluorine, chlorine, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy,
R ^{4 represents} hydrogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy,
R ^{5 represents} hydrogen, cyano, halogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy,
R ⁶ represents alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy,
R ^{7 represents} hydrogen, halogen, in each case alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, each optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, or for each optionally substituted by halogen Alkenyl, alkenyloxy, alkenylthio, alkynyl, alkynyloxy or alkynylthio each having 2 to 6 carbon atoms, and
R ^{8 represents} hydrogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy. 3. Compounds according to claim 1, characterized in that
R ^{1 represents} hydrogen, cyano, fluorine or chlorine,
R ^{2 stands} for cyano, thiocarbamoyl, fluorine, chlorine, bromine, or for methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, represents O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, methyl, ethyl, n- or i-propyl, propenyl, butenyl, propynyl, butinyl, methoxy, ethoxy, n- or i-propoxy, phenyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, or phenylsulfonyl,
A ¹ furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, methyl, ethyl, n- or i-propyl, methoxy , Ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A ² furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ³ for hydrogen, hydroxyl, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl substituted by fluorine, chlorine, methoxy or ethoxy, if appropriate -, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, 1-, s- or t-butoxy, n -, i-, s- or t-pentyloxy, methylthio, ethyl thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methyl sulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methyl sulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methyl amino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxy carbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynyl, optionally substituted by fluorine or chlorine amino, propynyloxy carbonyl or butynyloxycarbonyl, for each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy , Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclo-propylmethoxy, Cyclobutylmeth oxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclo pentylidenamino, Cyclohexylidenamino, Cyclopentyloxy carbonyl, Cyclohexyloxycarbonyl, Cyclyl, Carbonyl, Cycloxy, Nitrogen, or Cyclopentylhexoxy, cycloxy, cycloxy or carbonyl, cycloxy or carbonyl, cycloxy or carbonyl, cycloxy or carbonyl, cycloxy or carbonyl, cycloxy or carbonyl, or Bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyl oxy, phenyloxycarbonyl or Benzyloxycarbonyl stands,
A ³ furthermore represents dioxolanyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl,
however, A ¹ and A ² do not both simultaneously represent one of the radicals O, S, -SO- or -SO ₂ -, or
R ² and R ³ together represent one of the groupings below
-Q ¹ -CQ ² -, -Q ¹ -CQ ² -Q ¹ -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -Q ¹ -,
-C (R ⁹ , R ¹⁰ ) -CQ ² -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-Q ¹ -C (R ⁹ ) = C (R ⁹ ) -, -C (R ⁹ ) = C (R ⁹ ) -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² - ,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -, -C (R ⁹ ) = N-, -Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -CQ ² -N (R ¹¹ ) -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = C (R ⁹ ) -N (R ¹¹ ) -,
-C (R ⁹ ) = C (R ⁹ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = NN (R ¹¹ ) -,
-Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -,
Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -
in which
Q ¹ and Q ^{2 are the} same or different and each represents oxygen or sulfur,
R ⁹ and R ^{10 are the} same or different and individually represent hydrogen, fluorine, chlorine, methyl or ethyl or together represent ethane-1,2-diyl (dimethylene), and
R ^{11 represents} hydrogen, for methyl, ethyl, n- or i-propyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for propenyl optionally substituted by fluorine or chlorine, Butenyl, propynyl or butynyl, for each cyclopropyl or cyclopropyl methyl optionally substituted by fluorine, chlorine, methyl or ethyl, or for benzyl optionally substituted by cyano, fluorine, chlorine, methyl, ethyl, methoxy or ethoxy,
R ^{4 represents} hydrogen or methyl, ethyl, n- or i-propyl, n-, i- or s-butyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R ⁵ for hydrogen, cyano, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy stands,
R ⁶ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R ^{7 represents} hydrogen, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, Ethoxy, n- or i-propoxy, n-, 1-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino or dipropylamino, or for ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylthio optionally substituted by fluorine, chlorine or bromine, Butenylthio, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylthio or butynylthio, and
R ^{8 represents} hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy. 4. Compounds according to claim 1, characterized in that
R ^{1 represents} hydrogen, fluorine or chlorine,
R ^{2 represents} cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl,
R ^{3 represents} the grouping -A ¹ -A ² -A ³ ,
in which
A ^{1 represents} a single bond, O (oxygen), S (sulfur), -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, methyl, ethyl, propenyl, Butenyl, propynyl, methylsulfonyl, ethylsulfonyl, n- or i-propyl sulfonyl,
A ¹ furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, methyl, ethyl, methylsulfonyl, ethylsulfonyl, n- or i Propylsulfonyl,
A ² furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl or propene-1,3-diyl,
A ³ for hydrogen, hydroxyl, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl substituted by fluorine, chlorine, methoxy or ethoxy, if appropriate -, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, 1-, s- or t-butoxy, n -, 1-, s- or t-pentyloxy, methylthio, ethyl thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methyl sulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methyl sulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methyl amino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxy carbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynyl, optionally substituted by fluorine or chlorine amino, propynyloxy carbonyl or butynyloxycarbonyl, for each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy , Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclo-propylmethoxy, Cyclobutylmeth oxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclo pentylidenamino, Cyclohexylidenamino, Cyclopentyloxy carbonyl, Cyclohexyloxycarbonyl, Cyclyl, Carbonyl, Cycloxy, Nitrogen, or Cyclopentylhexoxy, cycloxy, cycloxy or carbonyl, cycloxy or carbonyl, cycloxy or carbonyl, cycloxy or carbonyl, cycloxy or carbonyl, cycloxy or carbonyl, or Bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyl oxy, phenyloxycarbonyl or Benzyloxycarbonyl stands,
A ³ furthermore represents furyl, tetrahydrofuryl, thienyl, dioxolanyl, oxazolyl, isoxazolyl or pyridinyl,
however, A ¹ and A ^{2 are} not both O, S, -SO-, -SO ₂ -, or
R ² and R ³ together represent one of the groupings below
-Q ¹ -CQ ² -, -Q ¹ -CQ ² -Q ¹ -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -Q ¹ -,
-C (R ⁹ , R ¹⁰ ) -CQ ² -, -C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -,
-Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -Q ¹ -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -,
-Q ¹ -C (R ⁹ ) = C (R ⁹ ) -, -C (R ⁹ ) = C (R ⁹ ) -CQ ² -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² - ,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -, -C (R ⁹ ) = N-, -Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -,
-Q ¹ -CQ ² -N (R ¹¹ ) -, -Q ¹ -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -Q ¹ -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -,
-C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = C (R ⁹ ) -N (R ¹¹ ) -,
-C (R ⁹ ) = C (R ⁹ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -,
-N (R ¹¹ ) -C (R ⁹ ; R ¹⁰ ) -CQ ² -N (R ¹¹ ) -, -C (R ⁹ ) = NN (R ¹¹ ) -,
-Q ¹ -CQ ² -C (R ⁹ , R ¹⁰ ) -N (R ¹¹ ) -,
Q ¹ -C (R ⁹ , R ¹⁰ ) -C (R ⁹ , R ¹⁰ ) -CQ ² -N (R ¹¹ ) -
in which
Q ¹ and Q ^{2 are the} same or different and each represents oxygen or sulfur,
R ⁹ and R ^{10 are the} same or different and individually represent hydrogen, fluorine, chlorine, methyl or ethyl or together represent ethane-1,2-diyl (dimethylene), and
R ^{11 represents} hydrogen, each represents methyl or ethyl which is optionally substituted by fluorine, methoxy or ethoxy, or represents propenyl, butenyl, propynyl or butinyl which is optionally substituted by fluorine or chlorine,
R ^{4 represents} hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine,
R ^{5 stands} for hydrogen, cyano, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine,
R ⁶ represents methyl or ethyl which is optionally substituted by fluorine or chlorine,
R ^{7 represents} hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine, and
R ^{8 represents} hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy. 5. A process for the preparation of compounds according to any one of claims 1 to 4, characterized in that arylhydrazones of the general formula (II)
in which
R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^{6 have} the meaning given in one of claims 1 to 4
With
Phosphonecarboxylic acid derivatives of the general formula (III)
in which
R ¹ and R ^{8 have} the meaning given in one of claims 1 to 4 and
R ¹² and R ¹³ each represent alkyl,
in the presence of a basic reaction auxiliary and in the presence of a diluent. 6. A method for controlling unwanted vegetation, thereby characterized in that at least one compound according to one of the Claims 1 to 4 on undesirable plants and / or their habitat can act. 7. Use of at least one compound according to one of the claims 1 to 4 for controlling unwanted plants. 8. Herbicidal agent, characterized by a content of a compound according to one of claims 1 to 4 and conventional extenders and / or surfactants.