DE10034803A1 - Substituted sulfonic acid anilides - Google Patents

Abstract

The invention relates to novel substituted sulphone acid anilides of formula (I), wherein R<1> represents hydroxy, nitro, cyano, carbamoyl, thiocarbamoyl, halogen or one of the following groups R<3>, Q<1>R<3>, Q<1>CQ<2>R<3>; R<2> respectively represents optional substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl; R<3> respectively represents optional substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl; X is hydrogen, cyano or halogen, and Z represents one of the known heterocyclic groups cited in the description, in addition to a method for the production and use thereof as a weed control agent (herbicide).

Description

The invention relates to new substituted sulfonic acid anilides, a process for their Production and their use as plant treatment agents, in particular as Herbicides.

It is already known that certain substituted sulfonic acid anilides are herbicidal Have properties (cf. EP-A-408382, EP-A-563384, EP-A-609734, EP-A- 648749, US-A-4818275, US-A-4909831, WO-A-95/17391, WO-A-95/29158, WO- A-95/29168, WO-A-95/30661, WO-A-96/18618).

 The properties of the Known substituted sulfonic acid anilides suffice among various Aspects do not meet the high requirements of modern plant treatment products.

There have now been new substituted sulfonic acid anilides of the formula (I)

in which
R ^{1 represents} hydroxy, nitro, cyano, carbamoyl, thiocarbamoyl, halogen or one of the following groups -R ³ , -Q ¹ -R ³ , -Q ¹ -CO ² -R ³ ,
R ^{2 represents} in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
R ^{3 represents} in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
X represents hydrogen, cyano or halogen, and
Z represents one of the heterocyclic groupings below,

in which
Q ^{1 represents} O (oxygen) or S (sulfur),
Q ^{2 represents} O (oxygen) or S (sulfur),
R ⁴ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, dialkylamino, cycloalkyl or Cycloalkylalkyl,
R ^{5 represents} hydrogen, hydroxy, amino, cyano, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl,
where appropriate two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - together for optionally substituted and / or optionally by O (oxygen), S (sulfur) or a grouping from the series - SO-, SO ₂ -, -NH- or -N (alkyl) - are interrupted alkanediyl or alkenediyl at the beginning (or at the end) or within the hydrocarbon chain,
Y ^{1 represents} O (oxygen), S (sulfur), SO, SO ₂ , NH, N (alkyl) or methylene and
Y ^{2 represents} a single bond or O (oxygen), S (sulfur), SO, SO ₂ , NH or N (alkyl),
where Y ¹ and Y ² are different in each individual case,
found.

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

Preferred substituents or preferred ranges of the radicals present in the formulas listed above and below are defined below.
R ¹ preferably represents hydroxy, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or one of the following groups -R ³ , Q ¹ -R ³ , -Q ¹ -CQ ² -R ³ .
R ² preferably represents alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each in each case optionally substituted by halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, in each case optionally by cyano, halogen or C ₁ -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 part, for each optionally substituted by cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ - C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy 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 part, or for each optionally by cyano, Nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ - haloalkoxy substituted heterocyclyl or heterocyclylalkyl with each 2 to 6 carbon atoms and 1 to 3 nitrogen atoms and / or 1 or 2 oxygen atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the alkyl part.
R ³ preferably represents alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, formyl (CHO), halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoximino-C ₁ -C ₄ alkyl alkenyl or alkynyl substituted by halogen, each having 2 to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the Part alkyl, for aryl or arylalkyl optionally substituted by cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy each 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ -Alkoxy or C ₁ -C ₄ -haloalkoxy substit uated heterocyclyl or heterocyclylalkyl each having 1 to 6 carbon atoms, optionally up to 4 nitrogen atoms and optionally up to 2 oxygen or sulfur atoms in the heterocyclyl group and optionally up to 4 carbon atoms in the alkyl part.
X preferably represents hydrogen, cyano, fluorine, chlorine or bromine.
Z preferably represents one of the heterocyclic groupings below

Q ¹ preferably represents O (oxygen).
Q ² preferably represents O (oxygen).
R ⁴ preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, alkyl optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy having 1 to 6 carbon atoms, each alkenyl optionally substituted by halogen or alkynyl each having 2 to 6 carbon atoms, each for alkoxy or alkoxycarbonyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, for each alkenyloxy or alkynyloxy optionally substituted by halogen each having 3 up to 6 carbon atoms, for alkylthio with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, for each optionally substituted by halogen alkenylthio or alkynylthio each with 3 to 6 carbon atoms, for alkylamino or dialkylamino each with 1 to 6 carbon atoms in the alkyl groups, or if necessary for each ge s partially substituted by cyano, halogen or C ₁ -C ₄ alkyl cycloalkyl or cycloalkylalkyl, each with 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl.
R ⁵ preferably represents hydrogen, hydroxyl, amino, cyano, for alkyl, alkoxy, alkoxycarbonyl or alkylamino, each optionally optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms, each optionally by halogen substituted alkenyl or alkynyl each having up to 6 carbon atoms, for each optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl-substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, or for phenyl or phenyl-C ₁ -C _{4 which are} optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy ₄ alkyl.
Two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - optionally together preferably stand for optionally substituted by halogen and / or optionally by O (oxygen), S (sulfur) or a group the series -SO-, SO ₂ -, -NH- or -N (C ₁ -C ₄ alkyl) - at the beginning (or at the end) or within the hydrocarbon chain under broken alkanediyl or alkenediyl, each with up to 5 carbon atoms.
Y ¹ preferably represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (C ₁ -C ₄ alkyl) or methylene.
Y ² preferably represents a single bond or O (oxygen), S (sulfur), SO, SO ₂ , NH or N (C ₁ -C ₄ alkyl).
Y ¹ and Y ² are different in each individual case.
R ¹ particularly preferably represents cyano, thiocarbamoyl, chlorine, bromine or tri fluoromethyl.
R ² particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t- which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy. Butyl, for each optionally substituted by fluorine, chlorine or bromine, propenyl, butenyl, ethynyl, propynyl or butinyl, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl , Cyclobutylmethyl, Cyclopentylmethyl or Cyclohexylmethyl, for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy , n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, naphthyl, benzyl or phenylethyl, or for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i -Propoxy, difluoromethoxy or trifluoro methoxy substituted heterocyclyl or heterocyclylalkyl from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridinyl, pyrimidinyl, furylmethyl, thienylmethyl, oxolylylethyl, pyrolylylethyl Pyridinylmethyl, pyrimidinylmethyl.
R ³ particularly preferably represents in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, formyl, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoximino methyl, ethoxyiminomethyl, methoximinoethyl or ethoxyiminoethyl , n-, i-, s- or t-butyl, for each optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally by cyano, fluorine, chlorine, bromine, methyl or Ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i -, S- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, naphthyl, benzyl or phenylethyl, or for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl , E thyl, n- or i-propyl, n-, 1-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclyl or heterocyclyl alkyl from the series furyl, tetrahydrofuryl , Thienyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, furylmethyl, furylethyl, furyl- (n- or i -) - propyl, tetrahydrofurylmethyl, tetrahydro furylethyl, tetrahydrofuryl- (n- or i - Dioxolanylmethyl, Di oxolanylethyl, Dioxolanyl- (n- or i -) - propyl, Pyridinylmethyl, Pyridinyl ethyl, Pyridinyl- (n- or i -) - propyl, Pyrimidinylmethyl, Pyrimidinylethyl, Pyrimidinyl- (n- or i -) - propyl.
X particularly preferably represents hydrogen, fluorine or chlorine.
Z particularly preferably represents one of the heterocyclic groupings below

R ⁴ particularly preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, and in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , n-, i-, s- or t-butyl, for each optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, for each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy Methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for propenyl oxy, butenyloxy, propynyloxy or butynyloxy, each optionally substituted by fluorine, chlorine or bromine, for each optionally by cyano, fluorine, chlorine , Methoxy or ethoxy substituted methylthio, ethylthio, n- or i-propylthio, for propenylthio optionally substituted by fluorine, chlorine or bromine, butenylthio, propinylthio or butinylthio, for methylamino, Ethylamino, n- or i-propylamino, dimethylamino or diethylamino, or for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl.
R ⁵ particularly preferably represents hydrogen, hydroxyl, amino, cyano, for each methyl, ethyl, n- or i-propyl, n-, optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, each optionally with fluorine, chlorine or bromine-substituted propenyl, butenyl, propynyl or butynyl, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, or for each optionally by nitro , Cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, di fluoromethoxy or trifluoromethoxy substituted phenyl, benzyl or phenylethyl.
Two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - optionally together are particularly preferably optionally substituted by fluorine or chlorine and / or optionally by O (oxygen), S (sulfur) or one Grouping from the series -SO-, SO ₂ -, -NH- or -N (methyl) - propane-1,3-diyl (trimethylene), butane-1, interrupted at the beginning (or at the end) or within the hydrocarbon chain, 4-diyl (tetramethylene), pentane-1,5-diyl (pentamethylene), propene-1,3-diyl, 1-butene-1,4-diyl or 2-butene-1,4-diyl.
Y ¹ particularly preferably represents O (oxygen), S (sulfur), SO, SO ₂ , NH, N (methyl) or methylene.
Y ² particularly preferably represents a single bond or O (oxygen), S (sulfur), SO, SO ₂ , NH or N (methyl).
Y ¹ and Y ² are different in each individual case.
R ¹ very particularly preferably represents cyano, thiocarbamoyl, chlorine or bromine.
R ² very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine or bromine, each optionally substituted by fluorine, chlorine or bromine Ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by fluorine, chlorine, bromine or methyl, each optionally optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl , n- or i-Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, naphthyl or benzyl, or for each optionally substituted by Cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclyl or heterocyclylalkyl from the series thienyl, pyrazolyl, oxa zolyl, isoxazolyl, thiazolyl, pyridinyl.
R ³ very particularly preferably represents in each case optionally, cyano, formyl, fluorine, chlorine and / or bromine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoximinomethyl or ethoximinomethyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, for in each case optionally substituted by fluorine, chlorine or methyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or for optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, or dioxolanylmethyl.
X very particularly preferably represents fluorine or chlorine.
R ⁴ very particularly preferably represents hydrogen, amino, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, which are each optionally substituted by fluorine, chlorine, methoxy or ethoxy. or t-butyl, for ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine, for methoxy, ethoxy, n- or i-propoxy, each optionally substituted by fluorine, chlorine, methoxy or ethoxy , Methylthio, ethylthio, n- or i-propylthio, for propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio or butynylthio, optionally substituted by fluorine, chlorine or bromine, or for each optionally by fluorine, chlorine or methyl substituted cyclopropyl or cyclopropylmethyl.
R ⁵ very particularly preferably represents hydrogen, amino, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, each for propenyl, butenyl, propynyl or butynyl, optionally substituted by fluorine, chlorine or bromine, for cyclopropyl or cyclopropylmethyl, each optionally substituted by fluorine, chlorine or methyl.

The individual radicals R ⁴ and R ⁵ - insofar as they are connected to the same heterocyclic grouping more than once, can have the same or different meanings in the context of the definitions given above as preferred, particularly preferred or very particularly preferred.

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

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

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

A very special group to be emphasized are the compounds of general formula (I), in which
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclopropyl optionally substituted by fluorine, chlorine, bromine or methyl, for each given if phenyl substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy tes heterocyclyl or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ^{3 represents} in each case optionally substituted by fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl .
X represents hydrogen, fluorine or chlorine, and
Z represents the heterocyclic grouping below,

in which
Q ^{1 stands} for O (oxygen),
R ⁴ for hydrogen, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for ethenyl, propenyl, butenyl, ethynyl optionally substituted by fluorine or chlorine, Propynyl or butynyl, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, for propenyloxy, butenyloxy, each optionally substituted by fluorine or chlorine , Propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio or butynylthio, or represents in each case optionally substituted by fluorine, chlorine or methyl, cyclopropyl or cyclopropylmethyl, and
R ⁵ for hydrogen, amino, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for each propeneyl, butenyl, propenyl or butinyl optionally substituted by fluorine or chlorine, for each optionally cyclopropyl or cyclopropylmethyl substituted by fluorine, chlorine or methyl.

Another group to be particularly emphasized are the compounds of the general formula (I), in which
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclopropyl optionally substituted by fluorine, chlorine, bromine or methyl, for each given if phenyl substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy tes heterocyclyl or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ^{3 represents} in each case optionally substituted by fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl .
X represents hydrogen, fluorine or chlorine, and
Z represents the heterocyclic grouping below,

in which
Q ^{1 stands} for O (oxygen),
Q ^{2 stands} for O (oxygen),
R ^{4-1 represents} hydrogen, chlorine, bromine or methyl,
R ^{4-2 represents} in each case optionally substituted by fluorine and / or chlorine methyl or ethyl, and
R ^{5 represents} hydrogen, amino, each represents methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, or represents propenyl or propynyl which is optionally substituted by fluorine or chlorine.

Another group to be particularly emphasized are the compounds of the general formula (I), in which
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclopropyl optionally substituted by fluorine, chlorine, bromine or methyl, for each given if phenyl substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for each optionally by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy sub substituted heterocyclyl or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ^{3 represents} in each case optionally substituted by fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl .
X represents hydrogen, fluorine or chlorine, and
Z represents the heterocyclic grouping below,

in which
R ^{4-1 represents} hydrogen, chlorine, bromine or methyl,
R ^{4-2 represents} in each case optionally substituted by fluorine and / or chlorine methyl, ethyl, methoxy or ethoxy, and
R ^{5 represents} in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy methyl, ethyl, n- or i-propyl, or for propenyl or propynyl which is optionally substituted by fluorine or chlorine.

Another group to be particularly emphasized are the compounds of the general formula (I), in which
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine or chlorine, for cyclopropyl optionally substituted by fluorine, chlorine, bromine or methyl, for each optionally phenyl substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy Heterocyclyl or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ^{3 represents} in each case optionally substituted by fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl .
X represents hydrogen, fluorine or chlorine, and
Z represents the heterocyclic grouping below,

Q ^{1 stands} for O (oxygen),
Q ^{2 stands} for O (oxygen),
R ^{1 represents} in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy methyl, ethyl, n- or i-propyl, or represents propenyl or propynyl which is optionally substituted by fluorine or chlorine, and
R ² represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, or represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy.

Another group to be particularly emphasized are the compounds of the general formula (I), in which
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclopropyl optionally substituted by fluorine, chlorine, bromine or methyl, for each given if phenyl substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy tes heterocyclyl or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ^{3 represents} in each case optionally substituted by fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl .
X represents hydrogen, fluorine or chlorine,
Z represents the heterocyclic grouping below,

in which
Q ^{1 stands} for O (oxygen), and
R ^{4 represents} hydrogen, fluorine, chlorine, bromine, in each case represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy.

Another group to be particularly emphasized are the compounds of the general formula (I), in which
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclopropyl optionally substituted by fluorine, chlorine, bromine or methyl, for each given if phenyl substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy tes heterocyclyl or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ^{3 represents} in each case optionally substituted by fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl .
X represents hydrogen, fluorine or chlorine,
Z represents the heterocyclic grouping below,

in which
Q ^{1 stands} for O (oxygen),
Q ^{1 stands} for O (oxygen),
R ^{4 represents} hydrogen, fluorine, chlorine, bromine, methyl or ethyl optionally substituted by fluorine, chlorine, metoxy or ethoxy, or methoxy or ethoxy optionally substituted by fluorine, chlorine, methoxy or ethoxy, and
R ⁵ represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy.

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

The new substituted sulfonic acid anilides of the general formula (I) have interesting biological properties. They are particularly characterized by strong herbicidal activity.

The new substituted sulfonic acid anilides of the general formula (I) are obtained if sulfonic acid anilides of the general formula (II)

in which
R ¹ , R ² , X and Z have the meaning given above, with sulfenoic acid halides of the general formula (III)

X ¹ -SR ³ (III)

in which
R ^{3 has} the meaning given above and
X ^{1 represents} halogen,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.

If, for example, N- [2-cyano-5- (4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl) -4-fluoro- phenyl] methanesulfonamide and fluorodichloromethanesulfonyl chloride as starting materials, the course of the reaction in the process according to the invention can be outlined by the following formula:

Formula (II) provides a general definition of the sulfonic acid anilides to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (II) R ^1, R ^2, X and Z preferably or in particular have those meanings which have already been mentioned above in connection with the description of United invention of the general formula (I) as preferred or as particularly preferred for R ¹ , R ² , X and Z have been specified.

The starting materials of the general formula (II) are known and / or can be according to processes known per se (cf. EP-A-408382, EP-A-563384, EP-A-609734, EP-A-648749, US-A-4818275, US-A-4909831, WO-A-95/17391, WO-A-95/29158, WO-A-95/29168, WO-A-95/30661, WO-A-96/18618, WO-A- 99/52878).

Formula (III) provides a general definition of the sulfenic acid halides to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (III), R ³ preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention preferably or as particularly preferred for R ³ ; X ¹ preferably represents fluorine, chlorine or bromine, especially chlorine.

The starting materials of the general formula (III) are known organic synthesis chemicals.

The process according to the invention for the preparation of the compounds of general Formula (I) is preferably carried out using a reaction aid guided. The usual reaction aids generally arrive organic or organic bases or acid acceptors. For this ge preferably hear alkali metal or alkaline earth metal acetates, amides, carbonates,  -hydrogen carbonates, -hydrides, -hydroxides or -alkanolates, such as Sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, Sodium, potassium or calcium hydroxide, sodium or potassium methoxide, -ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; continue too basic organic nitrogen compounds, such as trimethylamine, tri ethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-di methyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2.2.2] - octane (DABCO), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1.8 diazabicyclo- [5.4.0] -undec-7-en (DBU).

The process according to the invention for the preparation of the compounds of general Formula (I) is preferably carried out using a diluent leads. Inert organic solvents are particularly suitable as diluents Consideration. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as gasoline, benzene, Toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloro methane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, Propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethyl acetarnide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphorus säuretriamid; Esters such as methyl acetate or ethyl acetate, sulfoxides, such as dimethyl sulfoxide.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work  at temperatures between -60 ° C and + 60 ° C, preferably between -40 ° C and + 40 ° C.

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

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

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

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

Dicotyledon weeds of the genera

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

Dicotyledon cultures of the genera

Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera

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

Monocot cultures of the genera

Allium, pineapple, asparagus, avena, hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.

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

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

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

The active compounds according to the invention can be used in certain concentrations or Application rates also to control animal pests and fungal or bacterial plant diseases can be used. You can be opposed also as intermediates or precursors for the synthesis of other active ingredients deploy.

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

The treatment according to the invention of the plants and parts of plants with the active ingredients substances takes place directly or by influencing their surroundings, living space or Storage room according to the usual treatment methods, e.g. B. by diving, spraying,  Evaporation, misting, scattering, spreading and in the case of propagation material, in particular especially in the case of seeds, still by wrapping them in one or more layers.

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

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

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, and water.

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

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

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

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

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known herbicides and / or with substances which Improve crop tolerance ("safeners") for weed control ver can be used, whereby ready formulations or tank mixes are possible. It So mixtures with weed control agents are also possible, which a or contain several known herbicides and a safener.  

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

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

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

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

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

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

Preparation Examples

example 1

To a solution of 0.43 g (1 mmol) of N- [5- (3-amino-3,6-dihydro-2,6-dioxo-4-tri fluoromethyl 1 (2H) -pyrimidinyl) -2-chloro-4-fluoro-phenyl] -ethanesulfonamide in 6.5 ml of dichloromethane are added in succession at room temperature (approx. 20 ° C.) to 0.09 ml (1.1 mmol) pyridine and 0.12 ml (1.1 mmol) dichlorofluoromethanesulfenyl chloride. The The reaction mixture is stirred at room temperature for 18 hours, with 10 ml of dichloro diluted methane and successively with 2 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution wash, dried over magnesium sulfate and wide under reduced pressure freed from solvent. The crude product obtained in this way is columnar purified chromatographically on silica gel using dichloromethane as the eluent.

0.3 g (53% of theory) of N- [5- (3-amino-3,6-dihydro-2,6-dioxo-4-tri-fluoromethyl-1 (2H) -pyrimidinyl) -2-chloro are obtained -4-fluoro-phenyl] -N-dichlorofluoromethane sulfenyl-ethanesulfonic acid amide
LogP (at pH = 2, 3): 3.48.

Example 2

To a solution of 1.24 g (2.9 mmol) of N- [5- (3-amino-3,6-dihydro-2,6-dioxo-4-tri fluoromethyl-1 (2H) -pyrimidinyl) -2-chloro-4-fluoro-phenyl] -ethanesulfonamide in 10 ml of tetrahydrofuran are added with 0.15 g (3.8 mmol) of 60% sodium hydride Paraffin oil. The mixture is ge for about an hour at room temperature (about 20 ° C) stirred and then cooled to -35 ° C. Add one to the chilled solution -30 ° C from 0.28 g (1.55 mmol) tert-butyl disulfide, 0.13 ml (1.55 mmol) sulfuryl chloride and 10 ml of tetrahydrofuran prepared solution of tert-butylsulfenyl chloride. After a reaction time of 20 minutes, during which the reaction temperature rose to -5 ° C increases, the reaction mixture is mixed with 30 ml of ethyl acetate, after washed each other with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent is reduced Pressure largely removed and the crude product thus obtained is column chromato graphically cleaned over silica gel with dichloromethane as the eluent.

0.7 g (47% of theory) of N- [5- (3-amino-3,6-dihydro-2,6-dioxo-4-tri fluoromethyl-1 (2H) -pyrimidinyl) -2-chloro-4-fluoro-phenyl] -N-tert-butylsulfenyl-ethane sulfonic acid amide with a melting point of 205 ° C.

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

Table 1

Examples of the compounds of the formula (I)

The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromato graphy) on a phase inversion column (C 18). Temperature: 43 ° C.

• a) eluents for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^a) .
• b) eluents for determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^b) .

The calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values using the Retention times through linear interpolation between two consecutive Alkanones).

The lambda max values were determined using the UV spectra from 200 nm to 400 nm the maxima of the chromatographic signals determined.  

Anwendunssbeispiele Example A Pre-emergence test

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

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

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
0% = no effect (like untreated control)
100% = total annihilation

In this test, for example, the compounds according to the preparation example show 1, 2, 3 and 5 with good tolerance to crops, such as. B. Corn and wheat, very effective against weeds.  

Example 3 Post-emergence test

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

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

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

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

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

In this test, for example, the compounds according to the preparation example show 1, 2, 3 and 5 very strong action against weeds.

Claims (16)

1. Compounds of formula (I)
in which
R ^{1 represents} hydroxy, nitro, cyano, carbamoyl, thiocarbamoyl, halogen or one of the following groups -R ³ , -Q ¹ -R ³ , -Q ¹ -CQ ² -R ³ ,
R ^{2 represents} in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
R ^{3 represents} in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
X represents hydrogen, cyano or halogen, and
Z represents one of the heterocyclic groupings below,
in which
Q ^{1 represents} O (oxygen) or S (sulfur),
Q ^{2 represents} O (oxygen) or S (sulfur),
R ⁴ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, halogen, or for optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, di alkylamino, Cycloalkyl or cycloalkylalkyl,
R ^{5 represents} hydrogen, hydroxy, amino, cyano, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl or phenyl alkyl,
where optionally two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - together for optionally substituted and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO -, SO ₂ -, -NH- or -N (alkyl) - at the beginning (or at the end) or interrupted alkanediyl or alkenediyl within the hydrocarbon chain,
Y ^{1 represents} O (oxygen), S (sulfur), SO, SO ₂ , NH, N (alkyl) or methylene and
Y ^{2 represents} a single bond or O (oxygen), S (sulfur), SO, SO ₂ , NH or N (alkyl),
where Y ¹ and Y ² are different in each individual case. 2. Compounds of formula (I) according to claim 1, characterized in that
R1 represents hydroxy, nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or one of the following groups -R ³ , Q ¹ -R ³ , -Q ¹ - CQ ² -R ³ ,
R ² represents alkyl which is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy and has 1 to 6 carbon atoms,
for alkenyl or alkynyl, each optionally substituted by halogen, each having 2 to 6 carbon atoms,
for each cycloalkyl or cycloalkylalkyl which is optionally substituted by cyano, halogen or C ₁ -C ₄ -alkyl and has in each case 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part,
for each aryl or arylalkyl optionally substituted by cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy or arylalkyl, each with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part,
or for in each case optionally substituted by cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy heteroxyclyl or heterocyclylalkyl, each with 2 up to 6 carbon atoms and 1 to 3 nitrogen atoms and / or 1 or 2 oxygen atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the alkyl part,
R ^{3 is} alkyl which is optionally substituted by cyano, formyl (CHO), halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkoximino-C ₁ -C ₄ -alkyl and has 1 to 6 carbon atoms,
for in each case optionally substituted by halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, for in each case optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part,
for each aryl or arylalkyl optionally substituted by cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy or arylalkyl, each with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part,
or for in each case optionally substituted by cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy heteroxyclyl or heterocyclylalkyl each having 1 up to 6 carbon atoms, optionally up to 4 nitrogen atoms and optionally up to 2 oxygen or sulfur atoms in the heterocyclyl group and optionally up to 4 carbon atoms in the alkyl part,
X represents hydrogen, cyano, fluorine, chlorine or bromine, and
Z represents one of the heterocyclic groupings below,
in which
Q ^{1 stands} for O (oxygen),
Q ^{2 stands} for O (oxygen),
R ⁴ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, halogen, for alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy,
for alkenyl or alkynyl, each optionally substituted by halogen, each having 2 to 6 carbon atoms,
for alkoxy or alkoxycarbonyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having 1 to 6 carbon atoms in the alkyl groups,
for alkenyloxy or alkynyloxy, each optionally substituted by halogen, each having 3 to 6 carbon atoms,
for alkylthio with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy,
for alkenylthio or alkynylthio, each optionally substituted by halogen, each having 3 to 6 carbon atoms,
for alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups,
or represents in each case optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, and
R ⁵ for hydrogen, hydroxy, amino, cyano,
for alkyl, alkoxy, alkoxycarbonyl or alkylamino, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms,
for alkenyl or alkynyl, each optionally substituted by halogen, each having up to 6 carbon atoms,
for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part,
or in each case optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ - substituted alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ -haloalkoxy, phenyl or phenyl-C ₁ - C ₄ alkyl, wherein
two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - optionally together for optionally substituted by halogen and / or optionally by O (oxygen), S (sulfur) or a group from the Series -SO-, SO ₂ -, -NH- or -N (C ₁ - C ₄ alkyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl, each having up to 5 carbon atoms. 3. Compounds of formula (I) according to claim 1 or 2, characterized in that
R ^{1 represents} cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,
R ² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy,
for in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl,
for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl,
for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy , Difluoromethoxy or trifluoromethoxy substituted phenyl, naphthyl, benzyl or phenylethyl,
or for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i Propoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclyl or heterocyclylalkyl from the series furyl, thyrylyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, pyridinyl, pyrimidylmethyl, pyrolylmethyl, pyrolylmethyl, pyrylylethyl methyl stands,
R ³ for each methyl, ethyl, n- or i-propyl, n- or i-propyl, optionally substituted by cyano, formyl, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoximinomethyl, ethoxy iminomethyl, methoximinoethyl or ethoxyiminoethyl, n-, i-, s- or t-butyl,
for in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl,
for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl,
for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy , Difluoromethoxy or trifluoromethoxy substituted phenyl, naphthyl, benzyl or phenylethyl,
or for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i -Propoxy, difluoromethoxy or trifluoromethoxy-substituted heterocyclyl or heterocyclylalkyl from the series furyl, tetrahydrofuryl, thienyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, furyl- (furyl), furyl-, furyl-propyl, or furyl-methyl, furyl-propyl or furylethyl, Tetrahydrofurylmethyl, tetrahydrofurylethyl, tetrahydrofuryl- (n- or i -) - propyl, dioxolanyl methyl, dioxolanylethyl, dioxolanyl- (n- or i -) - propyl, pyridinyl methyl, pyridinylethyl, pyridinyl- (n- or i -) - propyl, Pyrimidinyl methyl, pyrimidinylethyl, pyrimidinyl- (n- or i -) - propyl,
X represents hydrogen, fluorine or chlorine,
Z represents one of the heterocyclic groupings below,
R ⁴ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, fluorine, chlorine, bromine,
for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
for in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl,
for methoxy, ethoxy, n- or i-propoxy, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
for propenyloxy, butenyloxy, propynyloxy or butynyloxy optionally substituted by fluorine, chlorine or bromine,
for methylthio, ethylthio, n- or i-propylthio optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
for propenylthio, butenylthio, propynylthio or butynylthio, each optionally substituted by fluorine, chlorine or bromine,
for methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino,
or for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, and
R ⁵ for hydrogen, hydroxy, amino, cyano,
for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy - or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino,
for propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine,
for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl,
or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i -Propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, benzyl or phenylethyl, where
two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - optionally together for optionally substituted by fluorine or chlorine and / or optionally by O (oxygen), 5 (sulfur) or a group from the Series -SO-, SO ₂ -, -NH- or -N (methyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted propane-1,3-diyl (trimethylene), butane-1,4- diyl (tetramethylene), pentane-1,5-diyl (pentamethylene), propene-1,3-diyl, 1-butene-1,4-diyl or 2-butene-1,4-diyl. 4. Compounds of formula (I) according to any one of claims 1 to 3, characterized in that
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine or bromine,
for in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl,
for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by fluorine, chlorine, bromine or methyl,
for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy , Difluoromethoxy or trifluoromethoxy substituted phenyl, naphthyl or benzyl,
or for each optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i Propoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclyl or heterocyclylalkyl from the series thienyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridinyl,
R ³ for methyl, ethyl substituted in each case by, cyano, formyl, fluorine, chlorine and / or bromine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoximinomethyl or ethoximinomethyl , n- or i-propyl, n-, i-, s- or t-butyl,
for in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl,
for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by fluorine, chlorine or methyl,
or for optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy , Difluoromethoxy or trifluoromethoxy substituted phenyl, or dioxolanylmethyl,
X represents fluorine or chlorine,
R ⁴ for hydrogen, amino, cyano, fluorine, chlorine, bromine,
for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine, chlorine, methoxy or ethoxy,
for in each case optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl,
for in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy, methoxy, ethoxy, n- or i-propoxy, methylthio, ethyl thio, n- or i-propylthio,
for propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio or butynylthio, each optionally substituted by fluorine, chlorine or bromine,
or represents in each case optionally substituted by fluorine, chlorine or methyl cyclopropyl or cyclopropylmethyl, and
R ^{5 represents} hydrogen, amino, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy,
for propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine,
or represents in each case optionally substituted by fluorine, chlorine or methyl cyclopropyl or cyclopropylmethyl. 5. Compounds of formula (I) according to claim 1, characterized in that
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclo propyl optionally substituted by fluorine, chlorine, bromine or methyl, for in each case optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for in each case optionally by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclic or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ³ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine or chlorine, or for phenyl optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl stands,
X represents hydrogen, fluorine or chlorine, and
Z represents the heterocyclic grouping below,
in which
Q ^{1 stands} for O (oxygen),
R ⁴ for hydrogen, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for ethenyl, propenyl, butenyl, ethynyl optionally substituted by fluorine or chlorine, Propynyl or butynyl, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, for propenyloxy optionally substituted by fluorine or chlorine, Butenyl oxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propynylthio or butynylthio, or represents cyclopropyl or cyclopropylmethyl which is optionally substituted by fluorine, chlorine or methyl, and
R ⁵ for hydrogen, amino, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine or chlorine, for each optionally by Fluorine, chlorine or methyl substituted cyclopropyl or cyclopropylmethyl. 6. Compounds of formula (I) according to claim 1, characterized in that
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclo propyl optionally substituted by fluorine, chlorine, bromine or methyl, for in each case optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for in each case optionally by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclic or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ³ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally substituted by fluorine or chlorine, or substituted, if appropriate, by fluorine, chlorine, bromine, methyl or trifluoromethyl Phenyl stands
X represents hydrogen, fluorine or chlorine, and
Z represents the heterocyclic grouping below,
in which
Q ^{1 stands} for O (oxygen),
Q ^{2 stands} for O (oxygen),
R ^{4-1 represents} hydrogen, chlorine, bromine or methyl,
R ^{4-2 represents} in each case optionally substituted by fluorine and / or chlorine methyl or ethyl, and
R ^{5 represents} hydrogen, amino, methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, or propenyl or propynyl, each optionally substituted by fluorine or chlorine. 7. Compounds of formula (I) according to claim 1, characterized in that
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclo propyl optionally substituted by fluorine, chlorine, bromine or methyl, for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy Heterocyclic or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ³ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally substituted by fluorine or chlorine, or substituted, if appropriate, by fluorine, chlorine, bromine, methyl or trifluoromethyl Phenyl stands
X represents hydrogen, fluorine or chlorine, and
Z represents the heterocyclic grouping below,
in which
R ^{4-1 represents} hydrogen, chlorine, bromine or methyl,
R ^{4-2 represents} in each case optionally substituted by fluorine and / or chlorine methyl, ethyl, methoxy or ethoxy, and
R ^{5 stands} for methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, or for propenyl or propynyl, each optionally substituted by fluorine or chlorine. 8. Compounds of formula (I) according to claim 1, characterized in that
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclo propyl optionally substituted by fluorine, chlorine, bromine or methyl, for phenyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or Trifluoromethoxy substituted heterocyclic or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ³ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, which is optionally substituted by fluorine or chlorine, or substituted, if appropriate, by fluorine, chlorine, bromine, methyl or trifluoromethyl Phenyl stands
X represents hydrogen, fluorine or chlorine, and
Z represents the heterocyclic grouping below,
Q ^{1 stands} for O (oxygen),
Q ^{2 stands} for O (oxygen),
R ^{1 represents} in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy methyl, ethyl, n- or i-propyl, or represents in each case optionally substituted by fluorine or chlorine propenyl or propynyl, and
R ^{2 stands} for methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, or for propenyl or propinyl, each optionally substituted by fluorine or chlorine. 9. Compounds of formula (I) according to claim 1, characterized in that
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclo propyl optionally substituted by fluorine, chlorine, bromine or methyl, for in each case optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for in each case optionally by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclic or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ³ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine or chlorine, or for phenyl optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl stands,
X represents hydrogen, fluorine or chlorine,
Z represents the heterocyclic grouping below,
in which
Q ^{1 stands} for O (oxygen), and
R ^{4 represents} hydrogen, fluorine, chlorine, bromine, or methyl or ethyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy. 10. Compounds of formula (I) according to claim 1, characterized in that
R ^{1 represents} cyano, thiocarbamoyl, chlorine or bromine,
R ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, optionally substituted by fluorine or chlorine, for cyclopro pyl optionally substituted by fluorine, chlorine, bromine or methyl, for in each case optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, or for in each case optionally by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted heterocyclic or heterocyclylalkyl from the series thienyl, pyrazolyl, isoxazolyl, pyridinyl,
R ³ for methyl, ethyl, n- or i-propyl, n-, 1-, s- or t-butyl, which is optionally substituted by fluorine or chlorine, or substituted, if appropriate, by fluorine, chlorine, bromine, methyl or trifluoromethyl Phenyl stands
X represents hydrogen, fluorine or chlorine,
Z represents the heterocyclic grouping below,
in which
Q ^{1 stands} for O (oxygen),
Q ^{1 stands} for O (oxygen),
R ^{4 represents} hydrogen, fluorine, chlorine, bromine, each represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or represents methoxy or ethoxy optionally substituted by fluorine, chlorine, methoxy or ethoxy, and
R ⁵ represents methyl or ethyl optionally substituted by fluorine, chlorine, methoxy or ethoxy. 11. A process for the preparation of compounds of the formula (I) according to claim 1, characterized in that sulfonic acid anilides of the general formula (II)
in which
R ¹ , R ² , X and Z have the meaning given above, with sulfenic acid halides of the general formula (III)
X ¹ -SR ³ (III)
in which
R ^{3 has} the meaning given above and
X ^{1 represents} halogen,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent. 12. Herbicidal agents, characterized by a content of at least one A compound of formula (I) according to claim 1. 13. Use of one or more compounds of the formula (I) according to Claim 1 for weed control.   14. A method of weed control, characterized in that to at least one compound of the formula (I) according to claim 1 Weeds and / or their habitat. 15. A process for the preparation of herbicidal compositions, characterized in that that at least one compound of formula (I) according to claim 1 with Extenders and / or surfactants mixed. 16. Use of herbicidal compositions according to claim 12 for combating of weeds.