EP2046781A2 - Substituted furyl-sulfonylamino(thio)carbonyl-triazoline(thi)ones - Google Patents

Abstract

The invention relates to novel substituted furyl sulfonylamino(thio)carbonyl triazoline(thi)ones of general formula (I), salts of the compounds of formula (I), methods for the production thereof, and the use thereof as herbicides.

Description

 description

Substituted furyl-sulfonylamino (thio) carbonyl-triazoline (thi) one

The invention relates to novel substituted furyl-sulfonylamino (thio) carbonyl-triazolin-(thi) ones, to processes and novel intermediates for their preparation and to their use as herbicides.

It is already known that certain substituted thienyl-sulfonylamino (thio) -carbonyl-triazolin (thi) ones have herbicidal properties (cf., WO-A-1997/016449, WO-A-1998/024787, WO-A-2001 / 005788, WO-A-2003/037086). However, the effect of these compounds is not satisfactory in all respects.

There have now been the new substituted furyl-sulfonylamino (thio) carbonyl-triazolin-(thi) one of the general formula (I)

in which

Q ^{1 is} O (oxygen) or S (sulfur),

Q ^{2 is} O (oxygen) or S (sulfur), R ^{a represents} hydrogen, cyano, nitro, halogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, alkenyloxy or alkynyloxy,

R ^{b is} hydrogen, cyano, nitro, halogen or each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, alkenyloxy or alkynyloxy,

R ^{c is} CO-Y

R ^{6 represents} hydrogen, hydroxyl, amino, cyano, alkylideneamino or each optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkylamino, alkylcarbonylamino, alkenyloxy, dialkylamino, cycloalkyl, cycloalkylamino, cycloalkylalkyl, aryl or arylalkyl,

R ^{7 is} hydrogen, hydroxyl, mercapto, amino, cyano, halogen or in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, alkylcarbonylamino, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino, alkynylamino, dialkylamino, aziridino, pyrrolidino , Piperidino, morpholino, cycloalkyl, cycloalkenyl, cycloalkyloxy,

Cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio, cycloalkylalkylamino, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or arylalkylamino, or

R ⁷ and R ⁶ together represent optionally branched alkanediyl, and

Y stands for one of the groupings OR ⁸ or N (R ⁹ R ¹⁰ ), where

R ^{8 is} in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, R ^{9 is} hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, and

R ^{10 is} hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,

- As well as salts of the compounds of formula (I) - found.

Saturated or unsaturated hydrocarbon moieties, such as alkyl, alkanediyl, alkenyl or alkynyl, are also in linkages with heteroatoms, such as in alkoxy

- as far as possible in each case straight-chain or branched.

Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substitution the substituents may be the same or different.

Preferred substituents or ranges of the radicals present in the formulas given above and below are defined below.

Q ¹ is preferably O (oxygen) or S (sulfur).

Q ² is preferably O (oxygen) or S (sulfur).

R ^a is preferably hydrogen, cyano, nitro, halogen, in each case optionally substituted by cyano, halogen or (C ₁ -CO-Alkoxy substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl group, or in each case optionally substituted by cyano or halogen alkenyl, alkynyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms in the alkenyl or alkynyl group. R ^b is preferably hydrogen, cyano, nitro, halogen, in each case optionally cyano, halogen or (Ci-C ₄ ) alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl group, or each optionally substituted by cyano or halogen alkenyl, alkynyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms in the alkenyl or alkynyl group.

R ^c is preferably CO-Y

R ⁶ is preferably hydrogen, hydroxy, amino, cyano, for (C ₂ -C ₁₀ ) -

Alkylideneamino, optionally substituted by fluorine, chlorine, bromine, cyano, (C ₁ -C ₄ ) -alkoxy, or substituted alkyl having 1 to 6 carbon atoms, in each case optionally substituted by fluorine, chlorine and / or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, in each case optionally by fluorine, chlorine, bromine,

Cyano, (C ₁ -CJ -alkoxy or substituted alkoxy, alkylamino or alkyl carbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, for alkenyloxy having 3 to 6 carbon atoms, for dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, in each case optionally by fluorine, chlorine, bromine, cyano and / or (C ₁ -C ₄ ) -

Alkyl-substituted cycloalkyl, cycloalkylamino or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or in each case optionally by fluorine, chlorine, bromine, cyano, nitro, (C ₁ -C ₄ ) -alkyl, Trifluoromethyl and / or (C ₁ -C ₄ ) - alkoxy substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety.

R ⁷ is preferably hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, optionally substituted by fluorine, chlorine, bromine, cyano, (C ₁ -

C ₄ ) -alkoxy, or (C 1 -C ₄ ) -alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, in each case optionally by fluorine, Chloro and / or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, in each case optionally substituted by fluorine, chlorine, cyano, (C ₁ -C ₄ ) -alkoxy or (C 1 -C 4 -alkoxy-carbonyl-substituted alkoxy, alkylthio , Alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, for alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino or alkynylamino each having 3 to 6 carbon atoms in the alkenyl or alkynyl group, for dialkylamino each having 1 to 4 Carbon atoms in the alkyl groups, in each case optionally substituted by methyl and / or ethyl aziridino, pyrrolidino, piperidino or morpholino, in each case optionally substituted by fluorine, chlorine, bromine, cyano and / or (C ₁ -C ₄ J-AIKyI substituted cycloalKyl, Cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino each having 3 to 6 carbon atoms in the cycloalkyl l- or cycloalkenyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or in each case optionally by fluorine, chlorine, bromine, cyano,

Nitro, (C _{r C4)} alkyl, trifluoromethyl, (C _r C ₄₎ -alkoxy and / or (C ₁ -C ₄₎ - alkoxycarbonyl, substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.

R ⁶ and R ⁷ are also preferably together optionally branched alkanediyl having 3 to 6 carbon atoms.

Y preferably represents one of the groupings OR ⁸ or N (R ⁹ R ¹⁰ ), where

R ⁸ is optionally substituted by cyano, halogen or (C-ι-C ₄₎ -alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents optionally cyano- or halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents in each case optionally by cyano, halogen or (Ci-C ₄ ) -

Alkyl substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 Carbon atoms in the alkyl moiety, each optionally substituted by nitro, cyano, halogen, (C 1 -C ₄ ) alkyl or (C 1 -C ₄ ) alkoxy substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or in each case optionally substituted by nitro, cyano, halogen, (C _r C ₄ ) alkyl or (Ci-C ₄ ) alkoxy substituted heterocyclyl or heterocyclylalkyl each having up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 to 2 oxygen or sulfur atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the alkyl part,

R ^{9 is} hydrogen or optionally cyano, halogen or (Ci-C ₄ ) - alkoxy-substituted alkyl having 1 to 6 carbon atoms, each optionally substituted by cyano or halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, each optionally optionally Cyano, halogen or (Ci-C ₄ ) alkyl substituted cycloalkyl or

Cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano, halogen, (Ci-C ₄ ) alkyl or (C ₁ -C ₄ ) - alkoxy substituted aryl or Arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4

Carbon atoms in the alkyl moiety, or for each optionally substituted by nitro, cyano, halogen, (Ci-C ₄ ) alkyl or (CrC ₄ ) alkoxy substituted heterocyclyl or heterocyclylalkyl each having up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 to 2 oxygen or sulfur atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the

Alkyl part is available, and

R ^{10 is} hydrogen or optionally cyano, halogen or (Ci-C ₄ ) -

Alkoxy-substituted alkyl having 1 to 6 carbon atoms, each optionally substituted by cyano or halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, each optionally substituted by cyano, halogen or (Ci-C ₄ ) alkyl substituted cycloalkyl or Cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano, halogen, (C ₁ -C ₄ ) alkyl or (C _r C ₄ ) - alkoxy substituted aryl or Arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4

Carbon atoms in the alkyl moiety, or for each optionally substituted by nitro, cyano, halogen, (Ci-C ₄ ) alkyl or (Ci-C ₄ ) alkoxy-substituted heterocyclyl or heterocyclylalkyl each having up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 to 2 oxygen or sulfur atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the

Alkyl part is.

Q ¹ particularly preferably represents O (oxygen) or S (sulfur).

Q ² is particularly preferably O (oxygen) or S (sulfur).

R ^a particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,

Methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or for each optionally cyano, fluorine or chlorine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy.

R ^b particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, in each case optionally cyano, fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or for in each case optionally cyano, fluorine or chlorine-substituted propenyl, Butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy.

R ^c is particularly preferably CO-Y

R ⁶ particularly preferably represents hydrogen, hydroxyl, amino, in each case optionally fluorine, chlorine, cyano, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for each optionally substituted by fluorine, chlorine and / or bromine substituted ethenyl, propenyl, butenyl, propynyl or butynyl, in each case optionally

Fluoro, chloro, cyano, methoxy or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i- , s- or t-butylamino, propenyloxy or butenyloxy, dimethylamino or diethylamino, in each case optionally fluorine, chlorine, methyl and / or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, Cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally substituted by fluorine, chlorine, methyl, trifluoromethyl and / or methoxy substituted phenyl or benzyl.

R ⁷ particularly preferably represents hydrogen, chlorine, bromine, in each case optionally by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case optionally substituted by fluorine, chlorine and / or bromine ethenyl, propenyl, butenyl , Ethynyl, propynyl or butynyl, in each case optionally substituted by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl-substituted 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, acetylamino or propionylamino, for propenyloxy, butenyloxy, Ethinyloxy, propinyloxy, butynyloxy, propenylthio, butenylthio, propynylthio, butynylthio, propenylamino, butenylamino, propynylamino or butynylamino, for dimethylamino, diethylamino or dipropylamino, in each case optionally substituted by fluorine, chlorine, methyl and / or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Cyclopentenyl,

Cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy,

Cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or each optionally substituted by fluoro, chloro, bromo, methyl, trifluoromethyl, methoxy or methoxycarbonyl

Phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino.

R ⁶ and R ⁷ are also particularly preferably together for trimethylene (propane-1, 3-diyl), tetramethylene (butane-1, 4-diyl) or pentamethylene (pentane-1, 5-diyl).

Y is particularly preferably one of the groupings OR ⁸ or N (R ⁹ R ¹⁰ ), where

R ^{8 is} in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case optionally substituted by cyano, fluorine or chlorine Propenyl, butenyl, propynyl or butynyl, in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, cyclopropyl, cyclobutyl, cyclopentyl,

Cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, in each case optionally by cyano, fluorine, chlorine, Bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or in each case optionally by cyano, fluorine, chlorine, bromine, methyl , Ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy substituted heterocyclyl or heterocyclylmethyl, wherein the

Heterocyclyl group is in each case selected from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl,

R ^{9 is} hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, in each case optionally by cyano, fluorine or chlorine-substituted propenyl, butenyl, propynyl or butynyl, in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, in each case optionally by cyano, fluorine, chlorine , Bromo, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or in each case optionally by cyano, fluorine, chlorine, bromine, Methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy substituted

Heterocyclyl or heterocyclylmethyl, wherein the heterocyclyl group is selected in each case from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, and

R ^{10 is} hydrogen, in each case optionally by cyano, fluorine, chlorine,

Methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case optionally substituted by cyano, fluorine or chlorine, propenyl, butenyl, propynyl or butynyl, in each case optionally Cyano, fluorine, chlorine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,

Cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i- Propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenylmethyl or phenylethyl, or in each case optionally by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy , Ethoxy, n- or i-propoxy substituted heterocyclyl or heterocyclylmethyl, wherein the heterocyclyl group is in each case selected from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl.

Q ¹ very particularly preferably represents O (oxygen).

Q ² is most preferably O (oxygen).

R ^a very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine or in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl.

R ^b is very particularly preferably hydrogen, fluorine, chlorine, bromine, iodine or in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl.

R ^c is very particularly preferably CO-Y

R ⁶ is very particularly preferably in each case optionally substituted by fluorine, chlorine,

Methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine or chlorine ethenyl, propenyl or

Propinyl, for each optionally substituted by fluorine, chlorine, methoxy or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, for dimethylamino, or cyclopropyl.

R ⁷ very particularly preferably represents hydrogen, chlorine, bromine, in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, in each case optionally Ethenyl, propenyl, butenyl, propynyl or butynyl which is fluorine- or chlorine-substituted, methoxy optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, propenyloxy, propynyloxy, propenylthio, propynylthio, propenylamino or propynylamino, dimethylamino or diethylamino, in each case optionally substituted by fluorine, chlorine or methyl, cyclopropyl, cyclopropyloxy, cyclopropylmethyl or cyclopropylmethoxy.

Y is most preferably the group OR ⁸ , where

R ^{8 is} in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl.

The invention preferably also the sodium, potassium,

Magnesium, calcium, ammonium, Di (C ₁ -C ₄ ) alkyl) ammonium, Th- ((C ^ -C ^ -alkyO sulfonium, C ₅ - or C ₈ -cycloalkyl-ammonium and di- C ^ _j ^ -C alkyl) - benzyl-ammonium salts of compounds of formula (I ), in which Q ¹ , Q ² , R ¹ , R ² , R ⁶ , R ⁷ and Y have the meanings given above as being preferred, particularly preferred or very particularly preferred.

The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and also correspondingly to the starting materials or compounds required in each case for the preparation

Intermediates. These remainder definitions can be combined with one another as desired, ie also between the specified preferred ranges.

Preferred compounds according to the invention are those compounds of the formula (I) which contain a combination of the meanings listed above as being preferred. Particularly preferred compounds according to the invention are those compounds of the formula (I) in which a combination of the meanings listed above as being particularly preferred is present.

Very particular preference according to the invention is given to those compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred.

A very particularly preferred group are the compounds of the formula (IA)

in which

R ^{2 is} R ^a and R ^{5 is} R ^b and wherein Q ¹ , Q ² , R ^a , R ^b , R ⁶ , R ⁷ and Y have the meanings given above as being preferred, particularly preferred or most particularly preferred.

R ^{2 is} particularly preferably hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R ^{5 is} hydrogen or methyl, and Q ¹ , Q ² , R ⁶ , R ⁷ and Y have the meanings given above as very particularly preferred ,

Another very particularly preferred group are the compounds of the formula (IB)

in which

R ^{4 is} R ^a and R ^{5 is} R ^b and wherein Q ¹ , Q ² , R ^a , R ^b , R ⁶ , R ⁷ and Y have the meanings given above as being preferred, particularly preferred or very particularly preferred.

R ^{4 is} very particularly preferably hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R ^{5 is} hydrogen or methyl and Q ¹ , Q ² , R ⁶ , R ⁷ and 'have the meanings given above as very particularly preferred.

Another very particularly preferred group are the compounds of the formula (IC)

in which R ^{4 is} R ^a and R ^{5 is} R ^b and wherein Q ¹ , Q ² , R ^a , R ^b , R ⁶ , R ⁷ and Y have the meanings given above as being preferred, particularly preferred or very particularly preferred.

R ^{4 is} very particularly preferably hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R ^{5 is} hydrogen or methyl, and Q ¹ , Q ² , R ⁶ , R ⁷ and Y have the meanings given above as very particularly preferred ,

The novel substituted furyl-sulfonylamino (thio) carbonyl-triazoline (thi) ones of the general formula (I) have interesting biological properties. They are characterized in particular by strong herbicidal activity.

The novel substituted furyl-sulfonylamino (thio) carbonyl-triazolin (thi) - one of the general formula (I), if one receives

(a) substituted furansulfonamides of the general formula (II)

in which

R ^a , R ^D and R ^c are as defined above,

with substituted triazolin (thi) ones of the general formula (III)

in which

Q ¹ , Q ² , R ⁶ and R ^{7 have} the abovementioned meaning and

Z is halogen, alkoxy, aryloxy or arylalkoxy,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or if you are

(b) substituted furyl-sulfonyliso (thio) cyanates of the general formula (IV)

in which

Q ¹ , R ^a , R ^b and R ^{c have} the abovementioned meaning,

with triazolin (thi) ones of the general formula (V)

in which

Q ² , R ⁶ and R ^{7 have} the abovementioned meaning, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or if

(c) substituted furan-sulfonic acid chlorides of the general formula (VI)

ci

^X O ^X R ^a in which

R ^a , R ^b and R ^{c have} the abovementioned meaning, with triazoline (thi) ones of the general formula (V)

in which Q ² , R ⁶ and R ^{7 have} the abovementioned meaning, and metal (thio) cyanates of the general formula (VII)

MQ ¹ -CN (VII) in which Q ^{1 has} the meaning given above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or if you are

(d) substituted furan-sulfonic acid chlorides of the general formula (VI)

Cl

^X O ^X R ^a

in which

R ^a , R ^b and R ^c are as defined above,

with triazolin (thi) on (thio) carboxamides of the general formula (VIII)

in which

Q ¹ , Q ² , R ⁶ and R ^{7 have} the abovementioned meaning,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or if you are

(e) substituted furyl-sulfonylamino (thio) carbonyl compounds of the general formula (IX)

in which

Q ¹ , R ^a , R ^b and R ^{c have} the abovementioned meaning and Z represents halogen, alkoxy, aryloxy or arylalkoxy,

with triazolin (thi) ones of the general formula (V)

in which

Q ² , R ⁶ and R ^{7 have} the abovementioned meaning,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

and, if appropriate, the compounds of the formula (I) obtained by processes (a), (b), (c), (d) or (e) are converted into salts by customary methods. If, for example, 2-chloro-4-ethoxycarbonyl-furan-3-sulfonamide and 4,5-dimethoxy-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting materials, cf. the course of the reaction in process (a) according to the invention can be outlined by the following formula scheme:

For example, using (2-fluoro-4-methoxycarbonyl-fur-3-yl-sulfonyl isothiocyanate and 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3 on as starting materials, the reaction sequence in process (b) according to the invention can be outlined by the following formula scheme:

For example, 4-methoxycarbonyl-2-trifluoromethyl-furan-3-sulfonic acid chloride, 5-ethyl-4-methoxy-2,4-dihydro-3H-1, 2,4-triazol-3-one and potassium cyanate are used as starting materials , the reaction sequence in the process (c) according to the invention can be outlined by the following formula scheme:

For example, use is made of 2-ethoxycarbonyl-4-methyl-furan-3-sulfonic acid chloride and 4-ethyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one-2-carboxamide as starting materials, the reaction sequence in process (d) according to the invention can be outlined by the following formula scheme:

For example, using N- (2-ethyl-4-i-propoxycarbonyl-fur-3-yl-sulfonyl) -O-phenyl-urethane and 4,5-dimethyl-2 ₎ 4-dihydro-3H-1, 2,4 triazol-3-one as starting materials, the reaction sequence in the process (e) according to the invention can be outlined by the following formula scheme:

The in process (a) for the preparation of compounds of general formula (I) as starting materials to be used substituted furan-3-sulfonamides are generally defined by the formula (II). In the general formula (II) R ^a have, R ^b and R ^c preferably or in particular have those meanings which (I) above in connection with the description of the compounds of the general formula as preferred or as particularly preferred for R ^a, R ^b and R ^{c have been} indicated.

The substituted furan-sulfonamides of the general formula (II) are partially not yet known from the literature; they are also the subject of the present application as new substances.

The substituted furan-sulfonamides of the general formula (II) are obtained when substituted furan-sulfonic acid chlorides of the general formula (VI)

in which

R ^a , R ^b and R ^c are as defined above,

with ammonia or with ammonium salts, such as ammonium acetate or ammonium carbonate, optionally in the presence of a diluent, such as water and / or methylene chloride, at temperatures between 0 ⁰ C and 100 ⁰ C (see the preparation examples).

The in process (a) for the preparation of compounds of general formula (I) as starting materials to be used substituted triazoline (thi) one are generally defined by the formula (III). In the general formula (III), Q ¹ , Q ² , R ⁶ and R ⁷ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of general formula (I) according to the invention preferably or as particularly preferred for Q ¹ , Q ² , R ⁶ and R ^{7 have been} specified.

The starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf., EP-A-341 489, EP-A-422 469, EP-A-425 948, EP-A-431 291, EP-A-507171, EP-A-534 266).

The in process (b) for the preparation of compounds of general formula (I) as starting materials to be used substituted furyl sulfonyl iso (thio) cyanates are generally defined by the formula (IV). In the general formula (IV), Q ¹ , R ^a , R ^b and R ^c preferably or in particular have those meanings which have already been mentioned above in connection with the description the compounds of the general formula (I) according to the invention have been indicated preferably or as particularly preferred for Q ¹ , R ^a , R ^b and R ^c .

The starting materials of the general formula (IV) can be prepared by conventional methods, for example by phosgenation of corresponding furan-sulfonamides of the formula (II) by customary methods.

The in process (b), (c) and (e) for the preparation of compounds of general formula (I) as starting materials to be used triazoline (thi) one are generally defined by the formula (V). In the general formula (V), Q ² , R ⁶ and R ⁷ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention or as particularly preferred for Q ² , R ⁶ and R ^{7 have been} specified.

The starting materials of the general formula (V) are known and / or can be prepared by processes known per se (cf., EP-A-341 489, EP-A-422 469, EP-A-425 948, EP-A-431 291, EP-A-507171, EP-A-534 266).

The in the inventive method (c) and (d) for the preparation of

Compounds of the general formula (I) as starting materials to be used substituted furan sulfonic acid chlorides are generally defined by the formula (VI). In the general formula (VI), R ^a , R ^b and R ^c preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention or as being particularly preferred for R ^a , R ^b and R ^{c have been} indicated.

The substituted furan-sulfonic acid chlorides of the general formula (VI) are known and / or can be prepared by processes known per se (cf., WO-A-2003/029245, WO-A-2003/082777, WO-A-2004/100946 ). The in process (d) for the preparation of compounds of general formula (I) as starting materials to be used triazoline (thi) on- (thio) - carboxamides are generally defined by the formula (VIII). In the general formula (VIII), Q ¹ , Q ² , R ⁶ and R ⁷ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of general formula (I) according to the invention preferably or as particularly preferred Q ¹ , Q ² , R ⁶ and R ^{7 have been} specified.

The starting materials of the general formula (VIII) can be prepared by processes known per se.

The in process (e) for the preparation of compounds of general formula (I) as starting materials to be used substituted furyl sulfonylamino (thio) carbonyl compounds are generally defined by the formula (IX). In the general formula (IX), Q ^1, R ^a, R ^b and R ^c preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) as preferred or as particularly preferred for Q ¹ , R ^a , R ^b and R ^{c have been} given.

The starting materials of the general formula (IX) can be prepared by processes known per se.

The processes (a), (b), (c), (d) and (e) according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using

Diluents performed. Suitable diluents are virtually all inert organic solvents. These include preferably aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and Dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone and dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphoric triamide.

As reaction auxiliaries in the processes (a), (b), (c), (d) and (e) according to the invention, it is possible to use all acid binders customarily used for such reactions. Preferably, alkali metal hydroxides, e.g. Sodium and potassium hydroxides, alkaline earth hydroxides, e.g. Calcium hydroxide, alkali metal carbonates and alcoholates such as sodium and potassium carbonate, sodium and potassium tert-butylate, furthermore basic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N-dimethylbenzylamine, N, N-dimethylaniline, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 2-ethyl, 4-ethyl and 5 Ethyl 2-methylpyridine, 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU) and 1,4-diazabicyclo [2,2,2] octane (DABCO).

The reaction temperatures in the processes (a), (b), (c), (d) and (e) according to the invention can be varied within a substantial range. In general, one works at temperatures between -20 ⁰ C and + 15O ⁰ C, preferably at temperatures between ^{0 0} C and + 100 ° C.

The processes (a), (b), (c), (d) and (e) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to work under elevated or reduced pressure.

To carry out the processes (a), (b), (c), (d) and (e) according to the invention, the particular starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the components used in each case in a larger excess. The reactions are generally carried out in a suitable diluent in the presence of a Acid acceptor performed, and the reaction mixture is stirred for several hours at the temperature required. The work-up is carried out in the processes (a), (b), (c), (d) and (e) according to the invention in each case by customary methods (compare the preparation examples).

Salts may optionally be prepared from the compounds of the general formula (I) according to the invention. Such salts are obtained in a simple manner by customary salt formation methods, for example by dissolving or dispersing a compound of formula (I) in a suitable solvent, e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base. The salts can then - be isolated by concentration or suction - optionally after prolonged stirring.

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

The compounds of the formula (I) according to the invention and their salts, referred to hereinafter together as compounds of the formula (I) according to the invention, have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients. It does not matter whether the substances are applied in the pre-sowing, pre-emergence or postemergence process. If the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage stage, But then they stop growing and finally die off after three to four weeks.

Upon application of the active ingredients to the green parts of the plants postemergence also occurs very quickly after treatment, a drastic halt in growth, and the weed plants remain in the existing stage of application growth stage or die after a certain time completely off, so that in this way one for the Crops harmful weed competition is eliminated very early and sustainably. Although the compounds of the invention have excellent herbicidal activity against mono- and dicotyledonous weeds

Crops of economically important crops such as e.g. Wheat, barley, rye, rice, maize, sugar beet, cotton and soya only marginally or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops.

In addition, the substances according to the invention have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant ingredients and facilitate harvesting, eg by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage can be reduced or completely prevented. Due to their herbicidal and plant growth regulatory properties, the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants. The transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known. Preference is given to the use of the compounds of the formula (I) according to the invention or salts thereof in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables. Preferably, the compounds of formula (I) as herbicides in

Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.

Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants. Alternatively, new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). In several cases, for example, genetic modifications of crop plants have been described for the purpose of modifying the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, US Pat.

WO 91/19806), transgenic crops which are resistant to certain herbicides of the type

Glufosinate (see, for example, EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659) are resistant, transgenic crops, for example, cotton, with the ability

Bacillus thuringiensis toxins (Bt toxins) that make the plants resistant to certain pests (E P-A-0142924, EP-A-0193259). Transgenic crops with modified fatty acid composition

(WO 91/13972). Numerous molecular biology techniques that can be used to produce novel transgenic plants with altered properties are known in principle; See, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed. CoId Spring Harbor Laboratory Press, ColD Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996 or Christou, "Trends in Plant Science" 1 (1996) 423-431).

For such genetic engineering, nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the aid of the abovementioned standard methods, z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments. The production of plant cells with a reduced activity of a

Gene product can be obtained, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.

For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical. In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are the See, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al. Plant J. 1 (1991), 95-106).

The transgenic plant cells can be regenerated to whole plants by known techniques. The transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.

Thus, transgenic plants are available which have altered properties by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

Preferably, the compounds (I) according to the invention can be used in transgenic cultures which are resistant to herbicides from the group of sulfonylureas, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances.

In the application of the active compounds according to the invention in transgenic crops, in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled

Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops. The invention therefore also relates to the use of the compounds of the formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating agents which contain compounds of the formula (I). The compounds of the formula (I) can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, and elevator Adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in: Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY , 1973; K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticides Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Publishing company, Stuttgart 1976;

Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.

On the basis of these formulations, it is also possible to prepare combinations with other pesticide-active substances, such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and / or growth regulators, for example in the form of a ready-to-use formulation or as a tank mix. Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants), eg polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate 2,2'-dinaphthylmethane-6,6 containing ¹ disulfonate, sodium dibutylnaphthalene-sulfonate or else sodium oleoylmethyltaurinate. To prepare the wettable powders, the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.

Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g. Polyoxyethylene.

Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding by means of commercially available bead mills and, if appropriate, addition of surfactants, as already listed above, for example, in the other formulation types. Emulsions, for example oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as they are already listed above, for example, in the other types of formulation produce. Granules can either be prepared by spraying the active ingredient onto adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers. Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material. For the preparation of plate, fluidized bed, extruder and spray granules, see for example methods in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff .; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For more details on pesticide formulation see, for example, GC Klingman, "Weed Control as a Science," John Wiley and Sons, Inc., New York, 1961, pp. 81-96, and JD Freyer, SA Evans, "Weed Control Handbook." 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

The agrochemical preparations generally contain 0.1 to 99 wt .-%, preferably 0.1 to 95 wt .-%, particularly preferably 0.5 to 90 wt .-% active ingredient of the formula (I). In wettable powders, the active ingredient concentration is for example about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components. For emulsifiable concentrates, the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%. Dusty formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used. In the water dispersible granules, the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%. In addition, the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent. In the case of using water as extender, for example, organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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.

Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Lignin sulphite liquors and methylcellulose.

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

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue 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.

The compounds of the formula (I) or salts thereof can be used as such or in the form of their formulations (formulations) with other pesticidally active substances, such as. As insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators can be used in combination, eg. B. as a ready-made formulation or as tank mixes. As a combination partner for the active compounds according to the invention in mixed formulations or in the tank mix, for example, known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-coenzyme A carboxylase, PS I ₁ PS II, HPPDO, phytoene desaturase, protoporphyrinogen Oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase based, can be used. Such compounds and also other useful compounds with partially unknown or other mechanism of action are, for example, in Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 11th edition 1997 (hereinafter also "PM") and 12. 2000 edition, The British Crop Protection Council and the Royal Soc. of Chemistry (publisher) and literature cited therein. Examples of known herbicides which can be combined with the compounds of the formula (I) are the following active compounds (note: the compounds are either with the "common name" according to the International Organization for Standardization (ISO) or with the chemical name , optionally together with a common code number): acetochlor; acifluorfen (-sodium); aclonifen; AKH 7088, ie methyl [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and acetic acid; alachlor; alloxydim (-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; amitrol; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azafenidin, azimsulfuron (DPX-A8947); aziprotryn; barban;

BAS 516H, i. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamide, benazoline (-ethyl); benfluralin; benfuresate; bensulfuron (-methyl); bensulide; bentazone; benzobicyclone, benzofenap; benzofluor; benzoylprop (-ethyl); benzthiazuron; bialaphos; bifenox; bispyribac (-sodium), bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil, butamifos; butenachlor; buthidazole; butraline; butroxydim, butylate; cafenstrole (CH-900); carbetamide; carfentrazone (-ethyl); caloxydim, CDAA, i. 2-chloro-N, N-di-2-propenylacetamide; CDEC, i. Diethyldithiocarbamic acid 2-chloroallyl ester; chlomethoxyfen; chloramben; chlorazifop-butyl, chloromesulon; chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron (-ethyl); chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; chlorotoluron, cinidone (-methyl and -ethyl), cinmethylin; cinosulfuron; clefoxydim, clethodim; clodinafop and its

Ester derivatives (e.g., clodinafop-propargyl); clomazone; clomeprop; cloproxydim; clopyralid; clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron (JC 940); cyanazine; cycloate; Cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (e.g., butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-D, 2,4-DB, dalaphone; desmedipham; Desmetryn; di-allate; dicamba; dichlobenil; dichloroprop; diclofop and its esters such as diclofop-methyl; diclosulam, diethatyl (-ethyl); difenoxuron; difenzoquat; diflufenican; diflufenzopyr, dimefuron; dimepiperate, dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethazone, dimexyflam, dimethipine; dimetrasulfuron, dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl;

EL 77, i. S-cyano-i, i, i-dimethylethyl, N-methyl-1H-pyrazoles, o-carboxamide; endothal; epoprodan, EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; Ethidimuron; ethiozin; ethofumesate; ethoxyfen and its esters (e.g.

HN-252); ethoxysulfuron, etobenzanide (HW 52); F5231, ie N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide; fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters, eg fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim; fentrazamide, fenuron; flamprop (-methyl or -isopropyl or -isopropyl-L); flazasulfuron; floazulate, florasulam, fluazifop and fluazifop-P and their esters, eg fluazifop-butyl and fluazifop-p-butyl; flucarbazone (sodium), fluchloralin; flumetsulam; flumeturon; flumiclorac (pentyl), flumioxazine (S-482); flumipropyn; fluometuron, fluorochloridone, fluorodifen; fluoroglycofen (-ethyl); flupoxam (KNW-739); flupropacil (UBIC-4243); flupyrsulfuron (-methyl or -sodium), flurenol (-butyl), fluridone; flurochloridone; fluroxypyr (-meptyl); flurprimidol, flurtamone; fluthiacet (methyl), fluthiamide, fomesafen; foramsulfuron, fosamine; furyloxyfen; glufosinate (-ammonium); glyphosate (-isopropylammonium); halo safen; halosulfuron (-methyl) and its esters (eg, methyl ester, NC-319); haloxyfop and its esters; haloxyfop-P (= R-haloxyfop) and its esters; hexazinone; imazamethabenz (-methyl); imazapyr; imazaquin and salts such as the ammonium salt; imazamethapyr, imazamox, imazapic, imazethamethapyr; imazethapyr; imazosulfuron; indanofan, ioxynil; isocarbamid; isopropalin; isoproturon; isouron; isoxaben; isoxachlortole, isoxaflutole, isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidide; mesosulfuron, mesotrione, metamitron; metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone; methyldymron; metabenzuron, methobenzuron; metobromuron; (Alpha-) metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MH; molinate; monalide; monocarbamide dihydrogen sulfates; monolinuron; monuron; MT 128, ie 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazineamine; MT 5950, ie N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazon; oxasulfuron, oxaziclomefone, oxyfluorfen; paraquat; pebulate; pelargonic acid, pendimethalin; pentoxazone, perfluidone; phenisopham; phenmedipham; picloram; picolinafen, pinoxaden, piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron (-methyl); procyazine; prodi amines; profluralin; proglinazine (-ethyl); prometon; prometryne; propachlor; propanil; propaquizafop and its esters; propazine; propham; propisochlor; propoxycarbazone- (sodium); Propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor; pyraflufen (-ethyl), pyrazolinates; pyrazon; pyrazosulfuron (-ethyl); pyrazoxyfen; pyribenzoxime, pyributicarb, pyridafol, pyridate; pyrimidobac (-methyl), pyrithiobac (-sodium) (KIH-2031); pyroxofop and its esters (eg propargyl esters); quinclorac; quinmerac; quinoclamine, quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives eg quizalofop-ethyl; quizalofop-P-tefuryl and -ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, ie 2- [4-chloro-2-fluoro-5- (2-propynyloxy) -phenyl] -4,5,6,7-tetrahydro-2H-indazole; secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, ie 2 - [[7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthalenyl] oxy] propanoic acid and methyl ester; sulcotrione, sulfentrazone (FMC-97285, F-6285); sulfazuron; sulfometuron (-methyl); sulfosate (ICI-A0224); sulfosulfuron, TCA; tebutam (GCP-5544); tebuthiuron; tepral oxydim, terbacil; terbucarb; terbuchlor; terbumeton; Terbuthylazine; terbutryn; TFH 450, ie N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1H-1, 2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiafluamide, thiazafluron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thifensulfuron (-methyl); thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triaziflam, triazofenamide; tribenuron (-methyl); triclopyr; tridiphane; trietazine; trifluralin; triflusulfuron and esters (eg, methyl ester, DPX-66037); trimeturon; tritosulfuron, tsitodef; vernolate; WL 110547, ie 5-phenoxy-1- [3- (fluoromethyl) phenyl] -1H-tetrazole; BAY MKH 6561, UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; Dowco-535; DK-8910; V-53482; PP-600; MBH-001; KIH-9201; ET-751; KIH-6127, KIH-485 and KIH-2023.

Of particular interest is the selective control of harmful plants in crops of commercial and ornamental plants. Although the compounds (I) according to the invention already have very good to sufficient selectivity in many cultures, in principle phytotoxicities can occur on the crop plants in some crops and, above all, in the case of mixtures with other herbicides which are less selective. Of particular interest in this regard are combinations of compounds of the formula (I) according to the invention which contain the compounds of the formula (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidote effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, eg. B. in economically important crops such as cereals (Wheat, barley, rye, corn, rice, millet), sugar beet, sugarcane, oilseed rape, cotton and soya, preferably cereals. The following groups of compounds are suitable, for example, as safeners for the compounds (I) and their combinations with further pesticides: a) compounds of the formulas (S-II) to (S-IV),

(S-II) (S-III) (S-IV)

where the symbols and indices have the following meanings: n 'is a natural number from 0 to 5, preferably 0 to 3; T is a (C ₁ or C ₂ ) alkanediyl chain which is unsubstituted or substituted by one or two (C ₁ -C ₄ ) -alkyl radicals or by [(C ₁ -C ₃ ) -alkoxy] -carbonyl; W is an unsubstituted or substituted divalent heterocyclic radical from the group of unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring N or O atoms, at least one N atom and at most one O atom in the ring, preferably a radical from the group (W1) to (W4),

(W1) (W2) (W3) (W4) m 'is 0 or 1; R ¹⁷ , R ¹⁹ are identical or different and are halogen, (C 1 -C ₄ ) -alkyl, (C 1 -C ₄ ) -alkoxy, nitro or (C 1 -C ₄ ) -haloalkyl; R ¹⁸ , R ²⁰ are identical or different OR ²⁴ , SR ²⁴ or NR ²⁴ R ²⁵ or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S. , which is connected via the N-atom with the carbonyl group in (S-II) or (S-III) and unsubstituted or by radicals from the group (C ₁ -CO-AIkVl, (C ₁ -C ₄ ) -alkoxy or optionally substituted phenyl, preferably a radical of the formula OR ²⁴ , NHR ²⁵ or N (CH ₃ ) ₂ , in particular of the formula OR ²⁴ R ²⁴ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 C -atoms;

R ²⁵ is hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₁ -C 6) -alkoxy or substituted or unsubstituted phenyl; R ^{x 'is} _H1 (Ci-Cβ) alkyl, _(Ci-C8) -haloalkyl, (C ₁ -C ₄₎ alkoxy (C ₁ -C ₈₎ -alkyl, cyano or

COOR ²⁶ wherein R ²⁶ is hydrogen, (Ci-C ₈₎ -alkyl, _(Ci-C8) -haloalkyl, (C ₁ -C ₄₎ - alkoxy- (C ₁ -C ₄₎ alkyl, (C ₁ - C ₆ ) -hydroxyalkyl, (C ₃ -C ₁₂ ) -cycloalkyl or Tn- (C ₁ -

C ₄₎ -alkyl-silyl; R ^27, R ^28, R ²⁹ are identical or different hydrogen, (Ci-C ₈₎ -alkyl, (C ₁ -C ₈₎ -

Haloalkyl, (C ₃ -C ₁₂ ) cycloalkyl or substituted or unsubstituted phenyl; R ²¹ is (Ci-C ₄₎ -alkyl, (C _{r C4)} -haloalkyl, (C ₂ -C ₄₎ alkenyl, (C ₂ -C ₄₎ haloalkenyl, (C ₃ -C ₇₎ cycloalkyl , preferably dichloromethyl;

R ^22, R ²³ is identical or different hydrogen, (dC ₄₎ alkyl, (C ₂ -C ₄₎ alkenyl, (C ₂ -C ₄₎ alkynyl, (Ci-C ₄₎ -haloalkyl, (C ₂ -C ₄₎ haloalkenyl, (CrC ₄₎ alkylcarbamoyl (Ci-C ₄₎ alkyl, (C ₂ -C ₄₎ -Alkenylcarbamoyl- (C ₁ -C ₄₎ alkyl, (C ₁ -C ₄ J -AIkOXy- (C ₁ -C ₄₎ - alkyl, dioxolanyl (CrC ₄₎ alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R ²² and R ²³ together form a substituted or unsubstituted heterocyclic Ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring, b) one or more compounds from the group: 1, 8-naphthalic anhydride,

Methyl-diphenylmethoxyacetat,

1 - (2-chlorobenzyl) -3- (1-methyl-1-phenylethyl) urea (cumyluron), 0,0-diethyl S-2-ethylthioethyl phosphorodithioate (disulfonone),

4-chlorophenyl methylcarbamate (mephenate),

0,0-diethyl-O-phenyl phosphorotioate (dietholate),

4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, CAS Regno: 31541-57-8),

Cyanomethoxyimino (phenyl) acetonitrile (Cyometrinil),

1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrinil),

4 ^{L of} chloro-2,2,2-trifluoroacetophenone O-1, 3-dioxolan-2-ylmethyloxime

(Fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim),

Benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole),

2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),

N- (4-methylphenyl) -N '- (1-methyl-1-phenylethyl) urea (Dymron),

(2,4-dichlorophenoxy) acetic acid (2,4-D), (4-chlorophenoxy) acetic acid,

(R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop),

4- (2,4-dichlorophenoxy) butyric acid (2,4-DB),

(4-chloro-o-tolyloxy) acetic acid (MCPA),

4- (4-chloro-o-tolyloxy) butyric acid, 4- (4-chlorophenoxy) butyric acid,

3,6-dichloro-2-methoxybenzoic acid (Dicamba),

1 - (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro) and their salts and esters, preferably (Ci-Ce);

c) N-acylsulfonamides of the formula (S-V) and their salts,

wherein R ^{30 is} hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical, a hydrocarbylthio radical or a heterocyclyl radical which is preferably bonded via a carbon atom, where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more identical or different radicals from the group halogen, cyano, nitro , Amino, hydroxy,

Carboxy, formyl, carbonamide, sulfonamide and radicals of the formula -Z ^a -R ^{a is} substituted, wherein each hydrocarbon moiety preferably has 1 to 20 carbon atoms and a C-containing radical R ³⁰ including substituents preferably 1 to 30 carbon atoms;

R ^{31 is} hydrogen or (C 1 -C 10 -alkyl, preferably hydrogen, or

R ³⁰ and R ³¹ together with the group of the formula -CO-N- denote the radical of a 3- to 8-membered saturated or unsaturated ring;

R ^{32 is} identical or different and is halogen, cyano, nitro, amino, hydroxyl, carboxy, formyl, CONH ₂ , SO ₂ NH ₂ or a radical of the formula -Z ^b -R ^b ;

R ^{33 is} hydrogen or (C 1 -C ₄ ) -alkyl, preferably H;

R ^{34 is} identical or different and is halogen, cyano, nitro, amino, hydroxyl, carboxy, CHO, CONH ₂ , SO ₂ NH ₂ or a radical of the formula -Z ^c -R ^c ;

R ^{a is} a hydrocarbon radical or a heterocyclyl radical, where each of the latter two radicals is unsubstituted or substituted by one or more identical or different radicals from the group of halogen, cyano, nitro, amino, hydroxyl, mono- and di- [(Ci-C ₄ ) - alkyl] -amino, or an alkyl radical in which several, preferably 2 or 3, non-adjacent CH ₂ groups are each replaced by an oxygen atom; R ^b , R ^{C are the} same or different or a hydrocarbon radical

Heterocyclylrest, wherein each of the last two radicals unsubstituted or by one or more identical or different radicals selected from the group halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halogeno (Ci-C ₄ ) alkoxy, mono- and di- (Ci-C ₄ ) -alkyl] -amino, or an alkyl radical in which several, preferably 2 or 3, not adjacent

CH ₂ groups are each replaced by an oxygen atom; Z ^{a is} a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-,

-O-CO-, -S-CO-, -SO-, -SO ₂ -, -NR * -, -CO-NR ^* -, -NR * -CO-, -SO ₂ -NR ^* - or -NR ^* -SO ₂ -, where the bond on the right of the respective divalent group is the bond to the radical R ^a and where the R ^* in the last-mentioned 5 radicals are each independently H, (dCO-alkyl or halo (Ci-C ^ - alkyl;

Z ^b , Z ^C independently of one another are a direct bond or a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-, -S-CO-, -SO-, -SO ₂ -, -NR * -, -SO ₂ -NR * -, -NR ^* -SO ₂ -, -CO-NR * - or -NR * -CO-, wherein the bond of the respective divalent group indicated on the right is the bond to the radical R ^b or R ^c and wherein the R ^* in the last-mentioned 5 radicals independently of one another are H, (C 1 -C 6 -alkyl or halo (C 1 -C ₄ ) -alkyl; n is an integer from 0 to 4, preferably 0, 1 or 2, in particular O or 1, and m is an integer from 0 to 5, preferably 0, 1, 2 or 3, in particular 0, 1 or 2;

d) Acylsulfamoylbenzoesäureamide of the general formula (S-Vl), optionally in salt form,

wherein

X ^{3 is} CH or N; R ^{35 is} hydrogen, heterocyclyl or a hydrocarbon radical, where the latter two radicals are optionally substituted by one or more, identical or different radicals from the group halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH ₂ , SO ₂ NH ₂ and Z ^{a '} -R ^{a' are} substituted; R ³⁶ is hydrogen, hydroxy, (Ci-C ₆₎ -alkyl, (C ₂ -C ₆₎ alkenyl, (C ₂ -C ₆₎ -alkynyl, (Ci-C ₆₎ - alkoxy, (C ₂ -C ₆ ) -Alkenyloxy, where the last five radicals mentioned optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, hydroxy, (Ci-C ₄ ) alkyl, (CrC ₄ ) alkoxy and (Ci-C ₄ ) - alkylthio substituted or

R ³⁵ and R ³⁶ together with the nitrogen atom carrying them

3- to 8-membered saturated or unsaturated ring;

R ^{37 is} halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH ₂ , SO ₂ NH ₂ or Z ^{b '} -R ^b' ;

R ³⁸ is hydrogen, (C _{r C4)} alkyl, (C ₂ -C ₄₎ -alkenyl or (C ₂ -C ₄₎ alkynyl;

R ^{39 is} halogen, cyano, nitro, amino, hydroxy, carboxy, phosphoryl, CHO, CONH ₂ ,

SO ₂ NH ₂ or Z ^c -R ^c ;

R ^{a is} a (C ₂ -C ₂ 0) -alkyl radical whose carbon chain is interrupted one or more times by oxygen atoms, heterocyclyl or a

Hydrocarbon radical, wherein the last two radicals are optionally substituted by one or more identical or different radicals from the group halogen, cyano, nitro, amino, hydroxy, mono- and di - [(CrC ₄ ) alkyl] amino;

R ^b, R ^{c are} identical or different and are a (C ₂ -C ₂ o) -alkyl radical whose carbon chain one or more times interrupted by oxygen atoms, is heterocyclyl or a hydrocarbon radical, where the last two radicals optionally substituted by one or more identical or different radicals from the group halogen, cyano, nitro, amino, hydroxyl, phosphoryl, (Ci-C ₄ ) -

Haloalkoxy, mono- and di - [(Ci-C ₄ ) alkyl] amino substituted; Z ^{a is} a divalent unit from the group O, S, CO, CS, C (O) O, C (O) S, SO, SO ₂ ,

NR ^d , C (O) NR ^{d '} or SO ₂ NR ^d' ;

Z ^b , Z ^C denote, identically or differently, a direct bond or a divalent unit from the group O, S, CO, CS, C (O) O, C (O) S, SO, SO ₂ , NR ^d , SO ₂ NR ^d or

C (O) NR ^{d '} ; R ^{d 'is} hydrogen, (C _r C ₄ ) -alkyl or (Ci-C ₄ ) -haloalkyl; n is an integer from 0 to 4, and in the case where X is CH, an integer of 0 to 5, and in the case where X is N, an integer of 0 to 4;

e) compounds of the acylsulfamoylbenzoic acid amide type, e.g. of the following formula (S-VII), e.g. are known from WO 99/16744,

eg those in which

R ²¹ = cyclopropyl and R ²² = H is (S-3-1 = 4-cyclopopylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide),

R ²¹ = cyclopropyl and R ²² = 5-CI is (S-3-2),

R ²¹ = ethyl and R ²² = H is (S-3-3),

R ²¹ = iso-propyl and R ²² = 5-CI is (S-3-4) and

R ²¹ = iso-propyl and R ²² = H is (S-3-5);

f) compounds of the type of N-acylsulfamoylphenylureas of the formula (S-VIII) which are e.g. are known from EP-A-365484,

where A is a radical from the group

R ^α and R ^ß independently hydrogen, (C ₁ -Ce) -Al ky I, (C ₃ -C ₈₎ cycloalkyl, (C ₃ -C ₆₎ -alkenyl, (C ₃ -C ₆₎ alkynyl .

^Rx

' ^NN or by (C ₁ -C ₄ ) -alkoxy or

RV

substituted (C ₁ -CJ-AIkOXy, or R ^α and R ^β together represent a (C 1 -C ₄ ) -alkylene bridge or a compound interrupted by oxygen, sulfur, SO, SO ₂ , NH or -N ((C 1 -C ₄ ) -alkyl) (C ₄ -C ₆ ) - Alkylene bridge,

R ^{γ 'is} hydrogen or (C _r C ₄ ) -alkyl,

R ^a and R ^b independently represent hydrogen, halogen, cyano, nitro, trifluoromethyl, (C ₁ -C ₄₎ alkyl, (dC ₄₎ -alkoxy, (C _{r C4)} alkylthio, (Ci-C ₄₎ -

Alkylsulfinyl, (Ci-C ₄ ) -alkylsulfonyl, -COOR ^j , -CONR ^k R ^{m '} , -COR "^' , -SO ₂ NR ^k R ^{m '} or -OSO ₂ - (Ci-C ₄ ) alkyl, or R ^a and R ^b together represent a (C ₃ -C ₄₎ - alkylene bridge, which may be substituted by halogen or (Ci-C ₄₎ -alkyl or (C ₃ -C ₄₎ -alkenylene, which by halogen or (C 1 -C ₄ ) -alkyl, or a C ₄ -Alkadienylenbrücke which may be substituted by halogen or (Ci-C ₄ ) alkyl, and R ⁹ and R ^{h are} independently hydrogen, halogen, (Ci C4) alkyl,

Trifluoromethyl, methoxy, methylthio or -COOR ^J , where R ^{c is} hydrogen, halogen, (C 1 -C ₄ ) -alkyl or methoxy, R cl 'is hydrogen, halogen, nitro, (Ci-C ₄₎ -alkyl, (dC ₄₎ alkoxy, (Ci-C ₄₎ alkylthio,

(Ci-C ₄₎ alkylsulfinyl, (C _r C ₄₎ alkylsulfonyl, -COOR ^r or -CONR ^k R ^{m ',} R ^e' is hydrogen, halogen, (Ci-C ₄₎ -alkyl, -COOR ^'', Trifluoromethyl or methoxy, or R ^d and R ^e together represent a (C ₃ -C ₄ ) -alkylene bridge, R ^{f is} hydrogen, halogen or (C ₁ -C ₄ ) -alkyl,

R ^x and R ^γ independently represent hydrogen, halogen, (C _{r C4)} alkyl, (Ci-C ₄₎ -

Alkoxy, (C ₁ -C ₄ ) -alkylthio, -COOR ^j , trifluoromethyl, nitro or cyano, R ^j , R ^k and R ^m independently of one another denote hydrogen or (C ₁ -C ₄ ) -alkyl, R ^k and R ^m together (C ₄ -C ₆ ) -alkylene bridge or an interrupted by oxygen, NH or -N ((Ci-C ₄ ) alkyl) - (C ₄ -C ₆ ) -alkylene bridge, and

R ^{n is} (C 1 -C ₄ ) -alkyl, phenyl or by halogen, (C 1 -C ₄ ) -alkyl, methoxy, nitro or

Trifluoromethyl substituted phenyl, preferably

1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea, 1- [4- (N-4, 5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea, 1- [4- (N-naphthoylsulfamoyl) phenyl] -3,3-dimethylurea,

g) compounds of the acylsulfamoylbenzoic acid amide type of the formula (S-IX) known from EP-A-1019368, optionally also in salt form,

wherein

R 101 is methyl, methoxy or trifluoromethoxy; R 102 is hydrogen, chlorine or methyl; R 103 is hydrogen, ethyl or propargyl; R ¹⁰⁴ is ethyl, cyclopropyl, isopropyl or propargyl, or R ¹⁰³ and R ¹⁰⁴ together form the group (CH ₂ ) -!

including the stereoisomers and the salts commonly used in agriculture.

Preferred herbicide-safener combinations comprising (A) a herbicidally effective amount of one or more compounds of formula (I) or their salts, and (B) an antidote effective amount of one or more safeners.

In the context of the invention, herbicidally effective amount means an amount of one or more herbicides which is suitable for negatively influencing plant growth. Antidote effective amount in the context of the invention means an amount of one or more safeners, which is suitable to reduce the phytotoxic effect of crop protection agents (eg of herbicides) on crop plants. The compounds of the formula (S-II) are described, for example, in EP-AO 333 131 (ZA-89/1960), EP-A-0 269 806 (US Pat. No. 4,891,057), EP-A-0 346 620 (AU-A 89/34951), EP-AO 174 562, EP-AO 346 620 (WO-A-91/08 202), WO-A-91/07 874 or WO-A 95/07 897 (ZA 94/7120) and the literature cited therein or can be prepared according to or analogously to the methods described therein. The compounds of the formula (S-III) are described in EP-A-0 086 750, EP-A-0 94349 (US-A-4,902,340), EP-A-0,917,336 (US-A-4,881,966) and EP-A-0 492 366 and there cited literature or can be prepared according to or analogously to the methods described therein. Some compounds are further described in EP-A-0 582 198 and WO 2002/34048. The compounds of formula (S-IV) are known from numerous patent applications, for example US-A-4,021,224 and US-A-4,021,229. Group B (b) compounds are further described in CN-A-87 / 102,789, EP-A-365484 and The Pesticide Manual, The British Crop Protection Council and the Royal Society of Chemistry, 11th edition, Farnham 1997, known. The compounds of group B (c) are described in WO-A-97/45016, those of group B (d) in WO-A-99/16744, those of group B (e) in EP-A-365484 and those of group B (g) described in EP-A-1019368.

The cited documents contain detailed information on preparation processes and starting materials and name preferred compounds. These documents are expressly referred to, they are by quotation as part of this description.

Preference is given to herbicide-safener combinations comprising safeners of the formula (S-II) and / or (S-III) in which the symbols and indices have the following meanings:

R ²⁴ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₃ -C ₁₂ ) -cycloalkyl, (C ₂ -C ₈ ) -alkenyl and (C ₂ -C ₈ ) -alkynyl, where the C-containing groups may be substituted by one or more, preferably up to three, radicals R ⁵⁰ ; R ⁵⁰ is identical or different halogen, hydroxy, (C 1 -C ₈ ) -alkoxy, (C 1 -C ₈ ) -

Alkylthio, (C ₂ -C ₈ ) -alkenylthio, (C ₂ -C ₈ ) -alkynylthio, (C ₂ -C ₈ ) -alkenyloxy, (C ₂ -C ₈ ) -alkinyloxy, (C ₃ -C ₇ ) - cycloalkyl, (C ₃ -C ₇₎ cycloalkoxy, cyano, mono- and di- ((CrC ₄₎ alkyl) amino, carboxy, _(Ci-C8) alkoxycarbonyl, (C ₂ -C ₈₎ -

Alkenyloxycarbonyl, (C CeJAlkylthiocarbonyl, (C ₂ -C ₈₎ -alkynyloxycarbonyl, (Ci-C ₈₎ alkylcarbonyl, (C ₂ -C ₈₎ alkenylcarbonyl, (C ₂ -C ₈₎ alkynylcarbonyl, 1- (hydroxyimino ) - (Ci-C ₆₎ alkyl, 1 - _[(Ci-C4) -alkylimino] - (Ci-C4) alkyl, 1 - [(CrC ₄₎ - alkoxyimino] - (CrC ₆₎ alkyl, (C ₁ -C ₈ -alkylcarbonylamino, (C ₂ -C ₈ ) -alkenylcarbonylamino, (C ₂ -C ₈ ) -alkynylcarbonylamino, aminocarbonyl, (C ₈ -C ₈ ) -

Alkylaminocarbonyl, di - ((Ci-C ₆₎ alkyl) aminocarbonyl, (C ₂ -Cβ) - alkenylaminocarbonyl, (C ₂ -C ₆₎ -Alkinylaminocarbonyl, (CrC ₈₎ - alkoxycarbonylamino, (dC ^ alkylaminocarbonylamino, ( CRCE) - alkylcarbonyloxy, which is unsubstituted or substituted by R ^51, (C ₂ -Cβ) - alkenylcarbonyloxy, (C ₂ -C ₆₎ -Alkinylcarbonyloxy, (CRCs) alkylsulfonyl, phenyl,

Phenyl (CRC6) alkoxy, phenyl (-C ₆₎ -alkoxycarbonyl, phenoxy, phenoxy- (CrC ₆₎ alkoxy, phenoxy (CrC ₆₎ -alkoxycarbonyl, phenylcarbonyloxy, Phenylcarbonylamino, phenyl- (C ₁ -C ₆ ) -alkylcarbonylamino, where the latter 9 radicals are unsubstituted in the phenyl ring or monosubstituted or polysubstituted, preferably up to three times, by radicals R ⁵² ; SiR ' ₃ , -O-SiR'3, R'3Si- (C 1 -C ₈ ) -alkoxy, -CO-O-NR' ₂ , -ON = CR ' _2l -N = CR' _2l -O-NR ' ₂₎ -NR ' _2l CH (OR ¹ J ₂ , -O- (CH ₂ ) _m -CH (OR') ₂ , -CR ^MI (OR ') ₂ , -O- (CH ₂ ) _m CR " ^l ( OR ") ₂ or by R" O-CHR '"CHCOR" - (C ₁ -C ₆ ) -alkoxy,

R ⁵¹ is identical or different halogen, nitro, (C 1 -C ₄ ) -alkoxy and unsubstituted or substituted with one or more, preferably up to three radicals R ⁵² phenyl; R ⁵² is identical or different halogen, (dC ₄₎ alkyl, (Ci-C ₄₎ alkoxy, _(Ci-C4) - haloalkyl, (Ci-C ₄₎ haloalkoxy or nitro;

R 'is identical or different hydrogen, (C 1 -C ₄ ) -alkyl, phenyl which is unsubstituted or substituted by one or more, preferably up to three, radicals R ⁵² or two radicals R' together form a (C ₂ -C ₆ ) - alkanediyl chain; R "is the same or different (C 1 -C ₄ ) -alkyl or two radicals R" together form a (C ₂ -C 6) -alkanediyl chain;

R '"is hydrogen or (C _r C ₄ ) alkyl; m is O, 1, 2, 3, 4, 5 or 6.

Particular preference is given to herbicide-safener combinations according to the invention containing safeners of the formula (S-II) and / or (S-III) in which the symbols and

Indices have the following meanings:

R ²⁴ is hydrogen, (C ₁ -C 5) -alkyl or (C ₃ -C ₇ ) -cycloalkyl, where the above C-containing radicals are unsubstituted or mono- or polysubstituted by halogen or one or two times, preferably simply, by radicals R ^{50 are} substituted,

R ⁵⁰ is identical or different hydroxyl, (C-ι-C ₄₎ alkoxy, carboxy, (C _{r C4)} - alkoxycarbonyl, (C ₂ -C ₆₎ alkenyloxycarbonyl, (C ₂ -C ₆₎ -alkynyloxycarbonyl, 1- (hydroxyimino) - (Ci-C ₄₎ alkyl, 1 - [(Ci-C ₄₎ AlkyliminoMCi-C ₄₎ -alkyl and 1 - [(Ci C ₄₎ -alkoxyimino] - (C ₁ -C ₄ ) -alkyl; -SiR ' ₃ , -ON = CR' ₂ , -N = CR ' _2l -NR' ₂ , and -O-NR ₂ , wherein R ^{1 is the} same or different hydrogen, (Ci-C ₄ ) -alkyl or in pairs one ( C ₄ -C ₅ ) alkanediyl chain, R ²⁷ , R ²⁸ , R ²⁹ are identical or different hydrogen, (C ₁ -Cs) -AIKyI, (Ci-C ₆ ) -

Haloalkyl, (C ₃ -C ₇ ) -cycloalkyl or phenyl which is unsubstituted or substituted by one or more of the radicals from the group halogen, cyano, nitro, amino, mono- and di- [(C 1 -C ₄ ) -alkyl] - amino, (dC ₄₎ alkyl, (Ci-C ₄₎ -haloalkyl, (CrC ₄₎ - alkoxy, (Ci-C ₄₎ haloalkoxy, (Ci-C ₄₎ alkylthio and (Ci-C ₄₎ - Alkylsulfonyl is substituted;

R ^{x 'is} hydrogen or COOR ²⁶ wherein R ²⁶ is hydrogen, (Ci-C _β) alkyl, (CrC ₈₎ - haloalkyl, (Ci-C ₄₎ alkoxy (Ci-C ₄₎ alkyl, (C -C ₆ ) -hydroxyalkyl, (C ₃ -C ₇ ) -cycloalkyl or tri (Ci-C ₄ ) -alkylsilyl, R ¹⁷ , R ¹⁹ are identical or different halogen, methyl, ethyl, methoxy, ethoxy, (Ci or C ₂ ) -haloalkyl, preferably hydrogen, halogen or (Ci or C ₂ ) - haloalkyl.

Very particular preference is given to safeners in which the symbols and indices in

Formula (S-II) have the following meanings: R ¹⁷ is halogen, nitro or (Ci-C ₄ ) haloalkyl; n 'is O, 1, 2 or 3;

R ¹⁸ is a radical of the formula OR ²⁴ ,

R ²⁴ is hydrogen, (Ci-CβJ-alkyl or (C ₃ -C ₇ ) -cycloalkyl, wherein the above

C-containing radicals are unsubstituted or mono- or polysubstituted, preferably up to three times, by identical or different halogen radicals or up to twice, preferably simply, by identical or different radicals from the group hydroxy, (C 1 -C ₄ ) -alkoxy (dC ₄₎ alkoxycarbonyl, (C ₂ -C ₆₎ - alkenyloxycarbonyl, (C ₂ -C ₆₎ -alkynyloxycarbonyl, 1 - (hydroxyimino) - _(Ci-C4) - alkyl, 1 - [(Ci-C ₄₎ -alkylimino] - (C _{r C4)} alkyl, 1 - [(Ci-C ₄₎ -alkoxyimino] - (Ci-C ₄₎ -alkyl and radicals of the formulas -SiR _'3, -ON = R' ₂ , -N = CR ₂ , -NR ' ₂ and -O-NR' _{2 are} substituted, wherein the radicals R ¹ in the above formulas are identical or different hydrogen, (Ci-C ₄ ) alkyl or in pairs (C ₄ or Cs) alkanediyl;

R ²⁷ , R ²⁸ , R ²⁹ are identical or different hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₆ ) -haloalkyl, (C ₃ -C ₇ ) -cycloalkyl or phenyl, which is unsubstituted or substituted by one or more of Radicals from the group halogen, (C 1 -C ₄ ) -alkyl, (C 1 -C ₄ ) -alkoxy, nitro, (C 1 -C ₄ ) -haloalkyl and (C 1 -C ₄ ) -haloalkoxy, and R ^x is hydrogen or COOR ²⁶ , wherein R ^{26 is} hydrogen, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkyl, (i.e. CeJ-hydroxyalkyl, (C ₃ -C ₇ ) -cycloalkyl or tri (C ₁ -C ₄ ) -alkylsilyl.

Very particular preference is also given to safeners of the formula (S-III) in which the symbols and indices have the following meanings: R ¹⁹ is halogen or (C 1 -C ₄ ) -haloalkyl; n 'is 0, 1, 2 or 3, wherein (R ¹⁹ J _n ^{1 is} preferably 5-Cl; R ²⁰ is a radical of the formula OR ²⁴ ; T is CH ₂ or CH (COO - ((C ₁ -C ₃ ) alkyl)) and R ²⁴ is hydrogen, (CrC ₈₎ -alkyl, (C _r -C ₈₎ -haloalkyl or (C ₁ -C ₄ J-AIkOXy- (C ₁ -C ₄₎ - alkyl, preferably hydrogen or (C 1 -C ₈ ) -alkyl.

Particularly preferred are safeners of the formula (II) in which the symbols and indices have the following meanings: W is (W1); R ¹⁷ is halogen or (C 1 -C 6 haloalkyl; n 'is 0, 1, 2 or 3, wherein (R ¹⁷ V is preferably 2,4-Cl ₂ ;

R ¹⁸ is a radical of the formula OR ²⁴ ;

R ²⁴ is hydrogen, (CrC ₈₎ -alkyl, (C _{r C4)} -haloalkyl, (Ci-C ₄₎ hydroxyalkyl, (C ₃ -

C ₇ ) -cycloalkyl, (C 1 -C ₄ ) -alkoxy- (C 1 -C ₄ ) -alkyl or tri (C ₁ -C ₂ ) -alkylsilyl, preferably (C ₁ -C ₄ ) -alkyl;

R ²⁷ is hydrogen, (C _r C ₈ ) -alkyl, (C _r C ₄ ) -haloalkyl or (C ₃ -C ₇ ) -cycloalkyl, preferably hydrogen or (C ₁ -C ₄ ) -alkyl, and R ^{x '} COOR ²⁶ wherein R ²⁶ is hydrogen, (Ci-C ₈₎ -alkyl, (Ci-C ₄₎ -haloalkyl, (C ₁ -C ₄₎ -

Hydroxyalkyl, (C ₃ -C ₇ ) -cycloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl or Tn- (C ₁ -C ₂ ) -alkylsilyl, preferably hydrogen or ( C ₄ ) alkyl.

Also particularly preferred are herbicidal compositions comprising a safener of the formula (S-II) ₁ in which the symbols and indices have the following meanings: W is (W ₂ );

R ¹⁷ is halogen or (C 1 -C 6 haloalkyl; n 'is 0, 1, 2 or 3, wherein (R ¹⁷ V is preferably 2,4-Cl ₂ ; R ¹⁸ is a radical of the formula OR ²⁴ ; R ²⁴ is hydrogen, (d-Cβ) -alkyl, (dd) -haloalkyl, (dC ₄ ) -hydroxyalkyl,

(C ₃ -C ₇ ) -cycloalkyl, ((C ₁ -C ₄ ) -alkoxy) - (C ₁ -C ₄ ) -alkyl or tri (C ₁ -C ₂ ) -alkyl-silyl, preferably (C 1 -C ₄ ) -alkyl , and

R ²⁷ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₃ -C ₇ ) -cycloalkyl or unsubstituted or substituted phenyl, preferably hydrogen, (d-)

C ₄ ) alkyl or phenyl which is unsubstituted or substituted by one or more

Radicals from the group halogen, (Ci-C ₄ ) -alkyl, (Ci-C ₄ ) -haloalkyl, nitro, cyano or (Ci-C ₄ ) -alkoxy is substituted.

Particular preference is also given to safeners of the formula (S-II) in which the symbols and indices have the following meanings: W is (W3);

R ¹⁷ is halogen or (C 1 -C ₂ ) haloalkyl; n 'is 0, 1, 2 or 3, wherein (R ¹⁷ ) _n ' is preferably 2,4-Cl ₂ ; R ¹⁸ is a radical of the formula OR ²⁴ ; R ²⁴ is hydrogen, (C 1 -C ₈ ) -alkyl, (C 1 -C ₄ ) -haloalkyl, (C 1 -C ₄ ) -hydroxyalkyl,

(C ₃ -C ₇ ) -cycloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl or tri (C ₁ -C ₂ ) -alkylsilyl, preferably (C ₁ -C ₄ ) -alkyl, and R ²⁸ is (C 1 -C 6) -alkyl or (C 1 -C ₄ ) -haloalkyl, preferably d-haloalkyl.

Particular preference is also given to safeners of the formula (S-II) in which the symbols and indices have the following meanings: W is (W4); R ¹⁷ is halogen, nitro, (C 1 -C ₄ ) -alkyl, (C 1 -C ₂ ) -haloalkyl, preferably CF ₃ , or

(C 1 -C ₄ ) -alkoxy; n 'is 0, 1, 2 or 3; m ¹ is 0 or 1; R ¹⁸ is a radical of the formula OR ²⁴ ; R ²⁴ is hydrogen, (dd) -alkyl, carboxy (dC ₄ ) -alkyl, (dC ₄ ) -alkoxycarbonyl-

(C 1 -C ₄ ) -alkyl, preferably (C 1 -C ₄ ) -alkoxy-CO-CH ₂ -, (C 1 -C ₄ ) -alkoxy-CO-C (CH ₃ ) H-, HO-CO-CH ₂ - or HO-CO- C (CH ₃ ) H-, and

R ²⁹ is hydrogen, (dC ₄₎ -alkyl, (dC ₄₎ -Ha! Oalkyl, (C ₃ -C ₇₎ -cycloalkyl or

Phenyl which is unsubstituted or substituted by one or more of the radicals Group halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, nitro, cyano and (C ₁ -C ₄ ) - alkoxy substituted.

The following groups of compounds are particularly suitable as safeners for the herbicidal active compounds of the formula (I): a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (ie of the formula (S-II) in which W = (W1) and (R ¹⁷ V = 2,4-Cl ₂ ), preferably compounds such as ethyl 1 - (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylate (S-IM ₁ mefenpyr-diethyl), Mefenpyr-dimethyl and mefenpyr (S-Il-O) ₁ and related compounds, as described in the

WO-A 91/07874 are described;

b) Derivatives of the dichlorophenylpyrazolecarboxylic acid (ie of the formula (S-II) in which W = (W 2) and (R ¹⁷ V = 2,4-Cb), preferably compounds such as 1- (2,4-dichlorophenyl) -5- Methyl-pyrazole-3-carboxylic acid ethyl ester (SI I-2), 1- (2,4-

Dichlorophenyl) -5-isopropyl-pyrazole-3-carboxylic acid ethyl ester (SI I-3), 1- (2,4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) -pyrazole-3-carboxylic acid ethyl ester (S-11- 4), 1- (2,4-dichlorophenyl) -5-phenyl-pyrazole-3-carboxylic acid ethyl ester (S-ll-5) and related compounds as described in EP-AO 333 131 and EP-A-0 269 806;

c) compounds of the type of the triazolecarboxylic acids (ie of the formula (S-II) in which W = (W3) and (R ¹⁷ V ⁼ 2,4-Cl ₂ ), preferably compounds such as fenchlorazolethyl, ie 1- (2 , 4-dichlorophenyl) -5-trichloromethyl- (1 H) -1, 2,4-triazole-3-carboxylic acid ethyl ester (S-ll-6), and related compounds (see

EP-A-0 174 562 and EP-A-0 346 620);

d) compounds of the type of 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or of 5,5-diphenyl-2-isoxazoline-3-carboxylic acid, such as isoxadifen (SI M 2), (in which W = ( W4), preferably compounds such as 5- (2,4-)

Dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (SI I-7) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S-II-8) and related compounds, such as they are described in WO-A-91/08202 or the ethyl 5,5-diphenyl-2-isoxazolinecarboxylate (S-II-9, isoxadifen-ethyl) or n-propyl ester (S-ll-10) or the 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S-11-11), as described in WO-A-95/07897.

e) compounds of the 8-quinolinoxyacetic acid type, for example those of the formula (S-III) ₁ in which (R ¹ V = 5-CI, R ²⁰ = OR ²⁴ and T = CH ₂ , preferably the compounds (5-chloro) 8-quinolinoxy) acetic acid (1-methylhexyl) ester (S-III-1, cloquintocetmexyl),

(5-chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-but-1-yl) ester (S-III-2), (5-chloro-8-quinolinoxy) acetic acid 4-allyl-oxy butyl ester (S-III-3), (5-chloro-8-quinolinoxy) acetic acid 1-allyloxy-prop-2-yl ester (S-III-4), (5-chloro-8-quinolinoxy) acetic acid ethyl ester (S. -III-5), (5-chloro-8-quinolinoxy) acetic acid methyl ester (S-III-6),

(5-chloro-8-quinolinoxy) allyl acetate (S-III-7), (5-chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (S-III-8), (5-chloro-8-quinolinoxy) acetic acid 2-oxo-prop-1-yl ester (S-III-9), (5-chloro-8-quinolinoxy) acetic acid (S-III-10) and its salts as they are eg in WO-A-2002/34048 and related compounds as described in EP-A-0 860 750, EP-A-0 094 349 and EP-A-0 191 736 or EP-A-0 492 366.

f) compounds of the (5-chloro-8-quinolinoxy) -malonic acid type, ie of the formula (S-III) in which (R ¹⁹ V = 5-CI, R ²⁰ = OR ²⁴ , T = -CH (COO-) Alkyl) -, preferably the compounds (5-chloro-8-quinolinoxy) -malonic acid diethyl ester (S-III-11), (5-chloro-8-quinolinoxy) -malonic acid diallyl ester, (5-chloro-8-quinolinoxy) -malonic acid methyl ethyl ester and related compounds, as described in EP-AO 582 198. g) compounds of the dichloroacetamide type, ie of the formula (S-IV) ₁ preferably:

N, N-diallyl-2,2-dichloroacetamide (dichloromide (S-IV-1), from US-A 4,137,070),

4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (IV-2, Benoxacor, from EP 0 149 974),

N1, N2-diallyl-N2-dichloroacetylglycine amide (DKA-24 (IV-3), from HU 2143821),

4-dichloroacetyl-1-oxa-4-aza-spiro [4,5] decane (AD-67),

2,2-dichloro-N- (1,3-dioxolan-2-ylmethyl) -N- (2-propenyl) acetamide (PPG-1292),

3-dichloroacetyl-2,2,5-thmethyloxazolidine (R-29148, S-IV-4), 3-dichloroacetyl-2,2-dimethyl-5-phenyloxazolidine,

3-dichloroacetyl-2,2-dimethyl-5- (2-thienyl) oxazolidine,

3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyloxazolidine (furilazole (S-IV-5),

MON 13900),

1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1,2-a] pymhamidin-6 (2H) -one (dicyclonone, BAS 145138),

h) compounds of group B (b), preferably

1, 8-naphthalic anhydride (S-b-1),

Methyl diphenylmethoxyacetate (S-b-2), cyanomethoxyimino (phenyl) acetonitrile (Cyometrinil) (S-b-3),

1 - (2-chlorobenzyl) -3- (1-methyl-1-phenylethyl) urea (cumyluron)

(S-b-4),

O, O-diethyl S-2-ethylthioethyl phosphorodithioate (disulfonone) (S-b-5),

4-chlorophenyl methylcarbamate (mephenate) (S-b-6), O, O-diethyl-O-phenylphosphorotioate (dietholate) (S-b-7),

4-Carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, CAS

Regno: 31541-57-8) (S-b-8),

1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrinil) (S-b-9),

4'-Chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime (Fluxofenim) (S-b-10),

4,6-dichloro-2-phenylpyrimidine (fenclorim) (S-b-11),

Benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole) (Sb-12),

2-Dichloromethyl-2-methyl-1,3-dioxolane (MG-191) (Sb-13), N- (4-methylphenyl) -N '- (1-methyl-1-phenylethyl) urea (Dymron) (Sb -14), (2,4-dichlorophenoxy) acetic acid (2,4-D),

(4-chlorophenoxy) acetic acid,

(R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB), (4-chloro-o-tolyloxy) acetic acid (MCPA), 4- (4-chloro-o-tolyloxy) butyric acid,

4- (4-chlorophenoxy) butyric acid, 3,6-dichloro-2-methoxybenzoic acid (Dicamba), 1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro) and their salts and esters, preferably (C ₁ -C ₈ ).

Preferred safeners are compounds of the formula (S-V) or theirs

Salts, in which

R ^{30 is} hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, furanyl or thienyl, where each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more substituents from the group consisting of halogen, (C ₁ -C ₄ ) -alkoxy, Halogen-

(C ₁ -C ₆ ) -alkoxy and (C 1 -C ₄ ) -alkylthio and in the case of cyclic radicals also (C 1 -C ₄ ) -alkyl and (C 1 -C ₄ ) -haloalkyl, R ^{31 is} hydrogen,

R ³² is halogen, halo (Ci-C ₄₎ alkyl, halo (Ci-C ₄₎ alkoxy, (dC ₄₎ alkyl, (Ci-C ₄₎ alkoxy, (dC ₄₎ alkylsulfonyl, ( C _r C ₄ ) -alkoxycarbonyl or (CrC ₄ ) -

Alkylcarbonyl, preferably halogen, (Ci-C ₄₎ -haloalkyl such as trifluoromethyl, (CrC ₄₎ - alkoxy, halo (dC ₄₎ alkoxy, (Ci-C ₄₎ alkoxycarbonyl or (CrC ₄₎ - alkylsulfonyl, R ³³ hydrogen,

R ³⁴ is halogen, (Ci-C ₄₎ alkyl, halo (Ci-C ₄₎ alkyl, halo (CrC ₄₎ alkoxy,

(C ₃ -C ₆₎ -cycloalkyl, phenyl, (Ci-C ₄₎ alkoxy, cyano, (Ci-C ₄₎ alkylthio, (CrC ₄₎ - Alkylsulfinyl, (Ci-C ₄₎ alkylsulfonyl, (Ci-C ₄₎ -alkoxycarbonyl or (C ₁ -C ₄₎ - alkylcarbonyl, preferably halogen, (dC ₄₎ alkyl, (Ci-C ₄₎ -haloalkyl, such as trifluoromethyl, halo (Ci-C ₄₎ alkoxy, (Ci-C ₄₎ -alkoxy or (C _r C ₄₎ -alkylthio, n is 0, 1 or 2 and m is 1 or. 2

Particular preference is given to compounds of the formula (SV) in which R ³⁰ = H ₃ CO-CH ₂ -, R ³¹ = R ³³ = H, R ³⁴ = 2-OMe (SV-1), R ³⁰ = H ₃ CO- CH ₂ -, R ³¹ = R ³³ = H, R ³⁴ = 2-OMe-5-CI is (SV-2), R ³⁰ = cyclopropyl, R ³¹ = R ³³ = H, R ³⁴ = 2-OMe SV-3), R ³⁰ = cyclopropyl, R ³¹ = R ³³ = H, R ³⁴ = 2-OMe-5-CI (SV-4), R ³⁰ = cyclopropyl, R ³¹ = R ³³ = H, R ³⁴ = 2-Me is (SV-5), R ³⁰ = tert. Butyl, R ³¹ = R ³³ = H ₁ R ³⁴ = 2-OMe is (SV-6).

Also preferred are safeners of the formula (S-VI) in which X ^{3 is} CH;

R ^{35 is} hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, (C ₂ -C ₆ ) -alkenyl, (C ₅ -C ₆ ) -cycloalkenyl, phenyl or 3 to 6 hetero-cyclic heterocyclyl having up to three heteroatoms from the group consisting of nitrogen, oxygen and sulfur, where the six last-mentioned radicals are optionally substituted by one or more identical or different substituents from the group halogen, (C ₁ -C ₆ ) -alkoxy, (C ₁ - Ce) -HaIOaIkOXy, (CrC ₂ ) alkylsulfinyl, (CrC ₂ ) alkylsulfonyl, (C ₃ -C ₆ ) -cycloalkyl, (Ci-C ₄ ) alkoxycarbonyl, (dC ^ alkylcarbonyl and phenyl and in the case of cyclic radicals also (C 1 -C ₄ ) -alkyl and (C 1 -C ₄ ) -haloalkyl;

R ^{36 is} hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₂ -C ₆ ) -alkenyl, (C ₂ -C ₆ ) -alkynyl, where the last three radicals mentioned are optionally substituted by one or more, identical or different substituents from the group halogen , hydroxy, (C ₁ -C ₄₎ - alkyl, (dC ₄₎ -alkoxy and (dC ₄₎ -alkylthio; R ³⁷ is halogen, (Ci-C ₄₎ -haloalkyl, (Ci-C ₄₎ -haloalkoxy, nitro, (Ci-C ₄₎ alkyl, (Ci-C ₄₎ - alkoxy, (Ci-C ₄₎ -alkylsulfonyl , (C 1 -C ₄ ) -alkoxycarbonyl or (C 1 -C ₄ ) -alkylcarbonyl;

R ^{38 is} hydrogen; R ^{39 is} halogen, nitro, (C 1 -C ₄ ) -alkyl, (dC ₄₎ -haloalkoxy, (C ₃ -C ₆₎ - cycloalkyl, phenyl, (Ci-C ₄₎ -alkoxy, cyano, (dC ^ alkylthio, (C _r C ₄₎ - alkylsulfinyl, (Ci-C ₄ ) Alkylsulfonyl, (C 1 -C ₄ ) -alkoxycarbonyl or (C 1 -C ₄ ) -alkylcarbonyl; n is 0, 1 or 2 and m is 1 or 2.

Preferred safeners of the formula (S-VII) are (S-3-1), (S-3-2), (S-3-3), (S-3-4) and (S-3-5).

Preferred safeners of the formula (VIII) are

1- [4- (N-2-Methoxybenzoylsulfamoyl) phenyl] -3-methylurea (S-VIII-1), 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea (S-VIII -2), 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea (S-VIII-3) and 1- [4- (N-naphthoylsulfamoyl) phenyl] -3,3-dimethylurea (S-VIII-4).

Preferred safeners of the formula S-IX are compounds of the formulas S-IX-A1 to S-IX-A4,

S-IX-A1 S-IX-A2

S-IX-A3 S-IX-A4

of which in turn the compound S-IX-A3 is particularly preferred as safener.

Particularly preferred combinations of herbicidal active compounds (A) as named in Table (I) and safeners (B) are those in which the safener (B) is selected from the group of safeners consisting of the compounds of the formulas S-II-1 ( Mefenpyr-diethyl), S-ll-9 (isoxadifen-ethyl), S-III-I (chloquintocet-mexyl), Sb-11 (fenclorim), Sb-14 (dymron), S-IX-A3 (4-cyclopropylaminocarbonyl N- (2-methoxybenzoyl) benzenesulfonamide N - ({4-

[(cyclopropylamino) carbonyl] phenyl} sulfonyl) -2-methoxybenzamides, very particularly preferred as safeners (B) are compounds S-ll-1 and S-IX-A3). Isoxadifen-ethyl is particularly preferred for use in rice. Particularly preferred for use in cereals are mefenpyr-diethyl, cloquintocetmexyl and 4-cyclopropylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide N- ({4 - [(cyclopropylamino) carbonyl] phenyl} sulfonyl) -2-methoxybenzamide, in Corn, in particular, isoxadifen-ethyl and 4-cyclopropylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide N - ({4 - [(cyclopropylamino) carbonyl] phenyl} sulfonyl) -2-methoxybenzamide. Isoxadifen ethyl is preferred for use in sugar cane.

A mixture with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil conditioners is also possible.

Some of the safeners are already known as herbicides and therefore, in addition to the herbicidal effect on harmful plants, also have a protective effect on the crop plants. The weight ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the particular safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20. The safeners can be formulated analogously to the compounds of the formula (I) or mixtures thereof with further herbicides / pesticides and provided and used as finished formulation or tank mixture with the herbicides.

With the external conditions such as temperature, humidity, the type of herbicide used, u.a. varies the required application rate of

Compounds of the formula (I). It can vary within wide limits, e.g. between 0.001 and 10.0 kg / ha or more of active substance, but is preferably between 0.005 and 5 kg / ha.

The active compounds of the invention may e.g. used in the following plants:

Dicotyledonous 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.

Dicotyledonous 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, Ishaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

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

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

The active compounds according to the invention are suitable for total weed control, depending on the concentration, e.g. on industrial and railway tracks and on paths and squares with and without tree cover. Likewise, the active compounds of the present invention may be used for weed control in permanent crops, e.g. Forestry, ornamental, fruit, wine, citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports lawns and grazing land and selective Weed control in one-year crops.

The compounds of the formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when applied to the soil and above-ground parts of plants. They also lend themselves, to some extent, to the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both preemergence and postemergence.

The preparation and the use of the active compounds according to the invention are evident from the following examples. Preparation Examples:

example 1

(Method (a))

0.44 g (1.76 mmol) of 5-methoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 40 ml of acetonitrile and at room temperature (ca. 20 ⁰ C) was added portionwise under stirring with 0.45 g (1.93 mmol) of 2,5-dimethyl-4-methoxycarbonyl-furan-3-sulfonamide and 0.29 g (1 93 mmol) of 1, 8- Diazabicyclo [5,4,0] undec-7-ene (DBU). The reaction mixture is stirred for 12 hours at room temperature and then concentrated under reduced pressure. The residue is taken up in 100 ml of methylene chloride, washed twice with 5% hydrochloric acid and once with water. The organic phase is filtered over sodium sulfate and filtered. The filtrate is concentrated in a water-jet vacuum and the remaining residue is crystallized from isopropanol. The resulting colorless solid is filtered off with suction, washed with diethyl ether and dried in air. This gives 0.45 g (66% of theory) of 4 - [[[(3-methoxy-4,5-dihydro-4-methyl-5-oxo-1H-1,2,4-triazol-1-yO -carbonyl-aminol-sulfonyl-α, δ-dimethyl-furan-S-carboxylic acid methyl ester (also known as 5-methoxy-4-methyl-2 - [(4-methoxycarbonyl-2,5-dimethyl-3-furyl) -sulfonyl] amino-carbonyl] -2,4-dihydro-3H-1, 2,4-triazol-3-one) (Compound with Ex-No. (IA-1) - of melting point 205 ° C.

Analogously to Example 1 and according to the general description of the preparation process according to the invention, for example, the compounds of general formula (I) - or of formulas (IA) to (IE) listed in Table 1 below - can be prepared.

Table 1a: Examples of the compounds of the formula (IA)

Table 1b: Examples of the compounds of the formula (IB)

Table 1c: Examples of the compounds of the formula (IC)

Starting materials of the formula (II):

Example (11-1)

In a solution of 3.0 g, (11.9 mmol) of 2,5-dimethyl-4-methoxycarbonyl-furan-3-sulfonic acid chloride in 40 ml of methylene chloride, 1.5 g of ammonia gas at 0 ^c C to 1O ⁰ C are introduced. The reaction mixture is then stirred for 15 hours at room temperature (about 20 ⁰ C) and then filtered. The filtrate is concentrated under reduced pressure, the resulting solid residue is stirred with petroleum ether and the crystalline product is isolated by suction. This gives 2.2 g (79% of theory) of 2,5-dimethyl-4-methoxycarbonyl-furan-3-sulfon-amide as a light beige solid of melting point 155 ° C.

Analogously to Example (11-1), for example, the following compounds of the general formula (II) can also be prepared:

Table 2a: Examples of the compounds of the formula (IIA)

Table 2b: Examples of the compounds of the formula (IIB) Table 2c: Examples of the compounds of the formula (HC)

Starting materials of the formula (VI):

Example (VI-1)

Step 1: 2,5-Dimethyl-furyl-3-carboxylic acid ethyl ester

11.5 g of sodium are placed in 75 ml of anhydrous dioxane under argon. A solution of 71.5 g (0.55 mol) of ethyl acetoacetate in 75 ml of anhydrous dioxane within 30 min. added dropwise .. After completion of the gas evolution, the solution is heated to 50 - 60 ⁰ C and added dropwise 68.5 g (0.5 mol) of bromoacetone. The mixture is then heated to 90-95 ⁰ C for 5 h. After cooling, the sodium bromide formed is filtered off, the solution is evaporated in vacuo and the residue is distilled. The fraction with the boiling point 88-95 ⁰ C / 1 mbar is dissolved in 100 ml of toluene, mixed with 0.3 ml of perchloric acid and heated to reflux on a water. After completion of the formation of water, the solution is distilled in vacuo. There are isolated 67.2 g (0.4 mol) of 2,5-dimethyl-furyl-3-carboxylic acid ethyl ester. Bp 99 - 101 ° C / 14mbar. Step 2: 2,5-Dimethyl-4-ethoxycarbonyl-3-chlorosulfonyl-furan

15.12 g (0.09 mol) of ethyl 2,5-dimethyl-furyl-3-carboxylate are dissolved in 30 ml of chloroform and admixed with 11.1 g (0.096 mol) of freshly distilled chlorosulfonic acid. It is heated to 65 ⁰ C for one hour, cooled to room temperature and treated with vigorous stirring in portions with 22.6 g (0.108 mol) of phosphorus pentachloride. Then, 30 ml of ortho-xylene are added and distilled off under atmospheric pressure, chloroform, phosphorus oxychloride and xylene. The residue is distilled in vacuo. 2,5-Dimethyl-4-ethoxycarbonyl-3-chlorosulfonyl-furan is obtained as a colorless oil. Yield: 11.1 g (52% of theory); Bp 118-119 ° C / 1mbar.

Analogously to Example (VI-1), it is also possible, for example, to prepare the following compounds of general formula (VI):

Table 3a: Examples of the compounds of the formula (VIA)

Table 3b: Examples of the compounds of the formula (VIB)

Table 3c: Examples of the compounds of the formula (VIC)

Starting materials of the formula (IV):

Sulfonyl isocyanates are prepared by known methods from a corresponding sulfonamide of the formula (II), an alkyl isocyanate such as n-butyl isocyanate, phosgene and a catalytic amount of 1, 4-diaza [2.2.2] bicyclooctane (DABCO) in XyIoI or other inert Solvent prepared with a sufficiently high boiling point (> 135 ⁰ C), cf. H. Ulrich and AAY Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, p. 223-241, Academic Press, New York and London, W. Foerst Ed. also WO 2003/033459.

Table 4a: Examples of the compounds of the formula (IVA)

Table 4b: Examples of the compounds of the formula (IVB)

Table 4c: Examples of the compounds of the formula (IVC) Application examples:

Example A

1. Pre-emergence herbicidal action

Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam in wood fiber pots and covered with soil. The test compounds formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then treated as an aqueous suspension with a

Water application amount of converted 800 l / ha with the addition of 0.2% wetting agent applied to the surface of the cover soil.

After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. The visual assessment of the damage to the test plants takes place after a test time of 3

Weeks compared to untreated controls

It means:

0% = no effect (as untreated control) 100% = total destruction

The following are the efficiencies of some of the claimed compounds on various weeds tested.

It means:

AVESA A vena sativa

LOLMU Lolium multiflorum

SETVI Setaria viridis

AMARE Amaranthus retroflexus

Sinal Sinapsis alba

STEME Stellaria media

In this test, for example, the compounds according to Preparation Examples IA-1, IA-2, IA-3, IA-6, IA-7 and IA-8 show very strong activity against weeds, in some cases with good compatibility with crop plants, such as corn and wheat , Example B

2. Post-emergence herbicidal action

Seeds of monocotyledonous or dicotyledonous crops are laid out in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage. The test compounds formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then sprayed onto the green parts of plants as an aqueous suspension with an application rate of 800 l / ha with the addition of 0.2% wetting agent. After about 3 weeks of life of the test plants in the greenhouse under optimal growth conditions, the effect of the preparations is scored visually compared to untreated controls (herbicidal activity in percent (%): 100% effect = plants are dead, 0% effect = like control plants).

It means:

0% = no effect (as untreated control) 100% = total destruction

AVESA Avena sativa

ECHCG Echinochloa crus-galli

LOLMU Lolium multiflorum

SETVI Setaria viridis

AMARE Amaranthus retroflexus

Sinal Sinapsis alba

STEME Stellaria media

In this test, for example, the compounds according to Preparation IA-1, IA-2, IA-3, IA-5, IA-6, IA-7, IA-8 and IA-9 exhibit, with partially good compatibility with crop plants, e.g. Corn and wheat, very strong against weeds.

Claims

claims

1. Substituted furyl-sulfonylamino (thio) carbonyl-triazoline (thi) -one of the general formula (I)

in which

Q ^{1 is} oxygen or sulfur,

Q ^{2 is} oxygen or sulfur,

R ^{a represents} hydrogen, cyano, nitro, halogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, alkenyloxy or alkynyloxy,

R ^{b is} hydrogen, cyano, nitro, halogen or each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, alkenyloxy or alkynyloxy,

R ^{c is} CO-Y

R ^{6 is} hydrogen, hydroxyl, amino, cyano, alkylideneamino or each optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkylamino, alkyl-carbonylamino, alkenyloxy, dialkylamino, cycloalkyl,

Cycloalkylamino, cycloalkylalkyl, aryl or arylalkyl, R ^{7 is} hydrogen, hydroxyl, mercapto, amino, cyano, halogen or in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, alkylcarbonylamino, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino, alkynylamino, dialkylamino,

Aziridino, pyrrolidino, piperidino, morpholino, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio, cycloalkylalkylamino, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or arylalkylamino, or

R ⁷ and R ⁶ together represent optionally branched alkanediyl, and

is one of the groupings OR ⁸ or N (R ⁹ R ¹⁰ ), where

R ^{8 is} in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,

R ^{9 is} hydrogen or each optionally substituted alkyl,

Alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, and

R ^{10 is} hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,

and the salts of compounds of the formula (I).

2. Compounds of formula (I) according to claim 1, characterized in that therein

Q ^{1 is} oxygen or sulfur,

Q ^{2 is} oxygen or sulfur

R ^{a is} hydrogen, cyano, nitro, halogen, in each case optionally substituted by cyano, halogen or (Ci-C ₄ ) alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6

Carbon atoms in the alkyl group, or represents in each case optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkynyl group,

R ^{b is} hydrogen, cyano, nitro, halogen, each optionally substituted by cyano, halogen or (Ci-C ₄ ) alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl group, or for each optionally substituted by cyano or halogen alkenyl, alkynyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms in the alkenyl or alkynyl group,

R ^{c is} CO-Y,

R ^{6 is} hydrogen, hydroxy, amino, cyano, (C ₂ -C ₁₀ ) -alkylideneamino, optionally substituted by fluorine, chlorine, bromine, cyano, (C ₁ -CJ -alkoxy, or (C 1 -C ₄ ) -alkoxycarbonyl-substituted alkyl having 1 to 6 carbon atoms, in each case optionally substituted by fluorine, chlorine and / or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, in each case optionally by fluorine, chlorine , Bromine, cyano, (C ₁ -C ₄ ) -alkoxy or (C ₁ -C ₆ -alkoxycarbonyl substituted alkoxy, alkylamino or alkyl-carbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, for alkenyloxy having 3 to 6 carbon atoms, for dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, in each case optionally by fluorine, chlorine, bromine, cyano and or (C, -C ₄ ) alkyl substituted

Cycloalkyl, cycloalkylamino or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, or in each case optionally by fluorine, chlorine, bromine, cyano, nitro, Trifluoromethyl and / or (C ₁ -C) -alkoxy substituted aryl or arylalkyl of 6 or 10, respectively

Carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part,

for hydrogen, hydroxy, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, optionally substituted by fluorine, chlorine, bromine, cyano, (C ₁ -C ₄ ) -

Alkoxy, (C ₁ -C ₄ ) -alkyl-carbonyl or (C., - C ₄ ) -Alkoxycarbonyl-substituted alkyl having 1 to 6 carbon atoms, each optionally substituted by fluorine, chlorine and / or bromine-substituted alkenyl or alkynyl in each case 2 to 6 carbon atoms, in each case optionally by fluorine, chlorine, cyano, (C ₁ -CJ -alkoxy or (C ₁ -C ₄ ) -

Alkoxy-carbonyl-substituted alkoxy, alkylthio, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, for alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino or alkynylamino each having 3 to 6 carbon atoms in the alkenyl or alkynyl group, for dialkylamino in each case 1 to 4

Carbon atoms in the alkyl groups, for each optionally substituted by methyl and / or ethyl aziridino, pyrrolidino, piperidino or morpholino, each optionally substituted by fluorine, chlorine, bromine, cyano and / or substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino,

Cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino each having 3 to 6 carbon atoms in the Cycloalkyl or cycloalkenyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or in each case optionally by fluorine, chlorine, bromine, cyano, nitro, (C ₁ -C ₄ -alkyl, trifluoromethyl, (C ₁ -C ₄ ) -alkoxy and / or (C 1, C ₄ ) alkoxycarbonyl-substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or

Arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety,

R ⁶ and R ⁷ together represent optionally branched alkanediyl having 3 to 6 carbon atoms,

Y stands for one of the groupings OR ⁸ or N (R ⁹ R ¹⁰ ), where

R ^{8 is} optionally cyano, halogen or (C 1 -C ₄ ) -alkoxy-substituted alkyl having 1 to 6 carbon atoms, in each case optionally cyano- or halogen-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, in each case optionally cyano, halogen or ( C ₁ -C ₄ J-AIKyI substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, each optionally substituted by nitro, cyano, halogen, (C ₁ - C ₄ ) alkyl or (C ₁ -C ₄ ) -alkoxy substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or in each case optionally by nitro, cyano, halogen, (C ₁ -C ₄ ) -alkyl or ( C ₁ -C ₄ -alkoxy-substituted heterocyclyl or heterocyclylalkyl having in each case up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 to 2 oxygen the sulfur atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the

Alkyl part is, R ⁹ represents hydrogen or represents optionally cyano-, halogen or (CrC ₄₎ -alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents optionally cyano- or halogen-substituted alkenyl or alkinyl each having 2 to 6 carbon atoms, represents in each case optionally cyano-, Halogen or (Ci-C ₄ ) -alkyl substituted

Cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, each optionally substituted by nitro, cyano, halogen, (C ₁ - C ₄ ) alkyl or (Ci-C ₄ ) alkoxy substituted Aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or in each case optionally by nitro, cyano, halogen, (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -alkoxy substituted heterocyclyl or heterocyclylalkyl each having up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 to 2 oxygen or sulfur atoms in the

Heterocyclylgruppe and optionally 1 to 4 carbon atoms in the alkyl part, and

R ^{10 is} hydrogen or optionally cyano, halogen or (Ci-C ₄ ) -alkoxy-substituted alkyl having 1 to 6 carbon atoms, each optionally substituted by cyano or halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, each optionally substituted by Cyano, halogen or (Ci-C ₄ ) alkyl substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in

Alkyl part, in each case optionally substituted by nitro, cyano, halogen, (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -alkoxy substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or in each case optionally by nitro, cyano, halogen, (C ₁ -C ₄ ) -alkyl or (C ₁ -)

C ₄ ) -alkoxy-substituted heterocyclyl or heterocyclylalkyl each having up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 to 2 oxygen or sulfur atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the alkyl part.

and the sodium, potassium, magnesium, calcium, ammonium, (C ₁ -C ₄ ) -

Alkyl ammonium, Tri (C ₁ -C ₄ ) alkyl) ammonium, C ₅ - or C ₈ -cycloalkyl-ammonium and di- ((C ₁ -C ₂ ) -alkyl) -benzyl-ammonium salts of compounds of the formula (I).

3. Compounds of formula (I) according to claim 1, characterized in that therein

Q ^{1 is} oxygen or sulfur,

Q ^{2 is} oxygen or sulfur,

R ^{a is} hydrogen, cyano, fluorine, chlorine, bromine, iodine, in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t butyl,

Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or for in each case optionally cyano, fluorine or chlorine-substituted propenyl, butenyl, propynyl, butynyl Propenyloxy, butenyloxy, propinyloxy or butynyloxy,

R ^{b is} hydrogen, cyano, fluorine, chlorine, bromine, iodine, in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t Butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-

Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, or in each case optionally by cyano, fluorine or Chlorine substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy,

R ^{c is} CO-Y,

R ^{6 is} hydrogen, hydroxy, amino, each optionally optionally

Fluorine, chlorine, cyano, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case optionally substituted by fluorine, chlorine and / or bromine substituted ethenyl, propenyl, Butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine,

Cyano, methoxy or ethoxy substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, propenyloxy or butenyloxy, dimethylamino or diethylamino, each optionally substituted by fluorine, chlorine, methyl and / or ethyl

Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each case optionally substituted by fluorine, chlorine, methyl, trifluoromethyl and / or methoxy-substituted phenyl or

Benzyl stands,

R ^{7 represents} hydrogen, chlorine, bromine, in each case optionally by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case optionally substituted by fluorine, chlorine and / or bromine substituted ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, in each case optionally substituted by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxy-carbonyl-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamines ", ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, acetylamino or propionylamino, for propenyloxy, butenyloxy, ethinyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio , Butinylthio, propenylamino, butenylamino, propynylamino or butynylamino, for dimethylamino,

Diethylamino or dipropylamino, in each case optionally substituted by fluorine, chlorine, methyl and / or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio,

Cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio,

Cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or in each case optionally substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy or methoxycarbonyl-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio,

Benzylthio, phenylamino or benzylamino,

R ⁶ and R ⁷ together for trimethylene (propane-1, 3-diyl), tetramethylene

(Butane-1,

4-diyl) or pentamethylene (pentane-1, 5-diyl),

Y stands for one of the groupings OR ⁸ or N (R ⁹ R ¹⁰ ), where

R ^{8 is} in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case optionally substituted by cyano, fluorine or chlorine Propenyl, butenyl, propynyl or butynyl, each optionally substituted by cyano, fluoro, chloro, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i -Propoxy, difluoromethoxy or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or represents in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy heterocyclyl or Heterocyclylmethyl, wherein the heterocyclyl group in each case from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl,

Tetrahydrothienyl is selected

R ^{9 represents} hydrogen or represents in each case optionally cyano, fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case optionally by cyano,

Propenyl, butenyl, propynyl or butynyl substituted by fluorine or chlorine, in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, in each case optionally by cyano, fluorine,

Chloro, bromo, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or in each case optionally by cyano, fluorine, chlorine, bromine , Methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy substituted heterocyclyl or heterocyclylmethyl, wherein the heterocyclyl group is selected in each case from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, and

R ^{10 is} hydrogen, in each case optionally by cyano, fluorine, chlorine,

Methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i, s- or t-butyl, each optionally substituted by cyano, fluorine or Chloro-substituted propenyl, butenyl, propynyl or butynyl, in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, in each case optionally by cyano, fluorine,

Chloro, bromo, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, or in each case optionally by cyano, fluorine, chlorine, bromine , Methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy substituted heterocyclyl or heterocyclylmethyl, wherein the heterocyclyl group is in each case selected from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl.

Compounds of formula (I) according to claim 1, characterized in that therein

Q ^{1 is} oxygen,

Q ^{2 is} oxygen,

R ^{a represents} hydrogen, fluorine, chlorine, bromine, iodine or represents in each case optionally fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl,

R ^{b represents} hydrogen, fluorine, chlorine, bromine, iodine or represents in each case optionally fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl,

R ^{c is} CO-Y, R ^{6 is} in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, in each case optionally substituted by fluorine or chlorine ethenyl, propenyl or propynyl, in each case optionally by fluorine, chlorine, methoxy or ethoxy substituted methoxy, ethoxy, n- or i-propoxy, represents dimethylamino, or represents cyclopropyl,

R ^{7 is} hydrogen, chlorine, bromine, in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy methyl, ethyl, n- or i-propyl, in each case optionally substituted by fluorine or chlorine ethenyl, propenyl , Butenyl, propynyl or butynyl, in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, Ethylamino, n- or i-propylamino, for propenyloxy, propynyloxy, propenylthio, propynylthio,

Propenylamino or propynylamino, for dimethylamino or diethylamino, in each case optionally substituted by fluorine, chlorine or methyl-substituted cyclopropyl, cyclopropyloxy, cyclopropylmethyl or cyclopropylmethoxy,

Y stands for the grouping OR ⁸ , where

R ^{8 is} in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl.

5. Compounds of the formula (IA)

in which

R ^{2 is} R ^a and R ^{5 is} R ^b and wherein Q ¹ , Q ² , R ^a , R ^b , R ⁶ , R ⁷ and Y have the meanings according to one of claims 1 to 4.

6. Compounds of formula (IA) according to claim 5, wherein R ^{2 is} hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R ^{5 is} hydrogen or methyl.

7. Compounds of the formula (IB)

in which

R ⁴ is R ^a, and R ⁵ is R ^b, and wherein Q ^1, Q ^2, R ^a, R ^b, R ^6, R ⁷ and Y have the meanings according to one of claims 1 to. 4

8. Compounds of formula (IB) according to claim 7, wherein R is hydrogen,

Methyl, trifluoromethyl, ethyl, propyl, isopropyl and R _{5 is} 5, for each hydrogen or methyl.

9. Compounds of the formula (IC)

in which

R ^{4 is} R ^a and R ^{5 is} R ^b and wherein Q ¹ , Q ² , R ^a , R ^b , R ⁶ , R ⁷ and Y have the meanings according to one of claims 1 to 4.

10. Compounds of the formula (IC) according to claim 9, where R ^{4 is} hydrogen, methylthylyl, tert-butyl fluoroethyl, ethyl, propyl, isopropyl and R ^{5 is} hydrogen or methyl.

11. A process for the preparation of compounds of the formula (I) according to claim 1, which comprises (a) substituted furanesulfonamides of the general formula (II)

in which

R ^a , R and R ^{c have} the meaning given in claim 1, with substituted triazolin (thi) ones of the general formula (III)

in which

Q ¹ , Q ² , R ⁶ and R ^{7 have} the meaning given in claim 1 and

Z is halogen, alkoxy, aryloxy or arylalkoxy,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or if you are

(b) substituted furyl-sulfonyl-iso (thio) cyanates of the general formula

(IV)

in which

Q ¹ , R ^a , R ^b and R ^{c have} the meaning given in claim 1,

with triazolin (thi) ones of the general formula (V)

in which

Q ² , R ⁶ and R ^{7 have} the meaning given in claim 1,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or if you are

(c) substituted furan-sulfonic acid chlorides of the general

Formula (VI)

in which

R ^a , R ^b and R ^{c have} the meaning given in claim 1,

with triazolin (thi) ones of the general formula (V)

in which

Q ² , R ⁶ and R ^{7 have} the meaning given in claim 1,

and metal (thio) cyanates of the general formula (VII)

MQ ¹ -CN (VII)

in which

Q ^{1 has} the meaning given in claim 1,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or if you are

(d) substituted furan-sulfonic acid chlorides of the general

Formula (VI)

in which R ^a , R ^b and R ^{c have} the meaning given in claim 1,

with triazolin (thi) on (thio) carboxamides of the general formula (VIII)

in which

Q ¹ , Q ² , R ⁶ and R ^{7 have} the meaning given in claim 1,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or if you are

(e) substituted furyl-sulfonylamino (thio) carbonyl compounds of the general formula (IX)

in which

Q, R ^a , R and R ^c have the meaning given in claim 1 and Z is halogen, alkoxy, aryloxy or arylalkoxy,

with triazolin (thi) ones of the general formula (V)

in which

Q ² , R ⁶ and R ^{7 have} the meaning given in claim 1,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

and, where appropriate, the compounds of the formula (I) obtained by processes (a), (b), (c), (d) or (e) by customary methods

Salts transferred.

12. A process for the preparation of substituted furan-sulfonamides of the formula

(II)

characterized in that furan-sulfonic acid chlorides of the general formula (VI)

in which

R ^a , R ^b and R ^{c have} the meaning given in claim 1,

with ammonia or with ammonium salts, optionally in the presence of a diluent, at temperatures between 0 ⁰ C and 100 ⁰ C.

13. A herbicidal composition, characterized by a content of at least one compound of the formula (I) according to claim 1.

14. Use of compounds of general formula (I) according to claim 1 for controlling unwanted plant growth.

15. A method for controlling weeds, characterized in that one lets compounds of the general formula (I) according to claim 1 act on the weeds or their habitat.

16. Process for the preparation of herbicidal agents, characterized in that compounds of the general formula (I) according to claim 1 are mixed with extenders and / or surface-active agents.