WO2002006277A1 - Substituted benzo-nitro-heterocycles and use thereof as herbicides - Google Patents

Abstract

The invention relates to novel substituted benzo-nitro-heterocycles of formula (I), wherein A represents a simple bond or the group C(R<2>,R<3>), R<2> representing hydrogen or alkyl and R<3> representing hydrogen or alkyl; Q represents O (oxygen) or S (sulphur), R<1> represents optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, respectively, X represents hydrogen or halogen, Y represents O (oxygen), S (sulphur), NH or N-R<1> and Z represents a heterocyclic group. The invention also relates to methods for producing said substituted benzo-nitro-heterocycles and to their use as herbicides.

Description

SUBSTITUTED BENZO NITROGEN HETEROCYCLES AND THE USE THEREOF AS HERBICIDES

The invention relates to new substituted benzo nitrogen heterocycles, a process for their production and their use as plant treatment agents, in particular as herbicides.

Numerous benzo nitrogen heterocycles with herbicidal properties have already become known (cf. US Pat. No. 4,755,217, cf. also DE-A-3 832 348, DE-A-3 922 107, DE-A-4208 778, EP-A -170 191, EP-A-263 299, EP-A-304 935, EP-A-

311 135, EP-A-328 001, EP-A-360 072, EP-A-379 894, EP-A-408 382, EP-A-415 642, EP-A-454444, EP-A-488 220 , EP-A-568 041, US-A-4761 174, US-A-5 084 084, US-A-5 281 571, WO-A-90/10626, WO-A-92/02509, WO-A -92/06962, WO-A-93/15074, WO-A-96/01254, WO-A-97/06150, WO-A-97/11060, WO-A-97/26248, WO-A-97 / 28127, WO-A-98/07720, WO-A-99/59983). However, the action of these compounds is not satisfactory in all respects.

The new substituted benzo nitrogen heterocycles of the formula (I)

in which

stands for a single bond or for the grouping C (R, R3)

in which

R represents hydrogen or alkyl, and

R represents hydrogen or alkyl, Q represents O (oxygen) or S (sulfur),

R ¹ represents optionally substituted alkyl, alkenyl, alkmyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,

X represents hydrogen or halogen,

Y represents O (oxygen), S (sulfur), NH or NR ¹ , and

for one of the heterocyclic groupings outlined below

(z ¹ ) (z ² ) (z ³ )

(z ⁴ ) (z ⁵ ) (z ⁶ )

(z ²² ) (z ²³ ) (z ²⁴ )

(z ²⁸ ) (z ²⁹ ) (z ³⁰ )

(z ³⁴ ) (z ³⁵ ) (z ³⁶ )

(z ³⁷ ) (z ³⁸ ) (z ³⁹ )

(z ⁴⁰ ) (z ⁴¹ ) (z ⁴² )

(z ⁴³ ) (z ⁴⁴ ) (z ⁴⁵ )

, 46 _x

(? 1 (z ⁴⁷ ) (z ⁴⁸ )

(z ⁴⁹ ) (Z ⁵⁰ ) (z ⁵¹ )

(z ⁵² ) (z ⁵³ ) where Ql represents O (oxygen) or S (sulfur),

Q ^{2 represents} O (oxygen) or S (sulfur),

R4 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 cycloalkyl or cycloalkyl stands,

R5 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 ^ and R ^, R5 and R ^ or

R4 and R5 - together for optionally substituted and / or optionally with O (oxygen), S (sulfur) or a group from the series -SO-, SO2-, -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,

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

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

A preferably represents a single bond or the grouping C (R ² , R ³ ),

in which

R ^{2 represents} hydrogen or alkyl having 1 to 6 carbon atoms, and

R ^{3 represents} hydrogen or alkyl having 1 to 6 carbon atoms.

Q is preferably O (oxygen).

R ¹ preferably represents alkyl with 1 to 6 carbon atoms optionally substituted by cyano, formyl (CHO), halogen, CrC ₄ alkoxy, C ₁ -C ₄ alkoximino or C ₁ -C ₄ alkylthio, each optionally substituted by cyano or

Halogen-substituted alkenyl or alkynyl each having 2 to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or Ci- alkyl, 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 by Νitro, amino, cyano,

Carboxy, carbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, Cι-C ₄ - alkoxy, _{Ci-C4-haloalkoxy,} -C ₄ alkylthio or C ₁ -C haloalkylthio 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 Νitro, amino, cyano, carboxy,

Carbamoyl, halogen, C ₁ -C alkyl, CrC ₄ haloalkyl, C ₁ -C alkoxy, Q- C ₄ -haloalkoxy, - -allylthio or Cr -haloalkylthio substituted 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, fluorine, chlorine or bromine.

Y preferably represents O (oxygen), S (sulfur), NH, N-CH ₃ or NC ₂ H ₅ .

Z preferably represents one of the heterocyclic groupings outlined below

(Z ³ ) (Z ⁹ ) (Z ¹¹ )

(z ¹² ) (z ¹³ ) (z ⁵² )

Ql 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 CrC-alkoxy having 1 to 6 carbon atoms, alkenyl or alkynyl each optionally substituted by halogen 2 to 6 carbon atoms, each for alkoxy or alkoxycarbonyl optionally substituted by cyano, halogen or -CC alkoxy or alkoxycarbonyl, each with 1 to 6 carbon atoms in the alkyl groups, for each optionally substituted by halogen alkenyloxy or alkynyloxy, each with 3 to 6 carbon atoms, for optionally alkylthio having 1 to 6 carbon atoms substituted by cyano, halogen or C1-C4alkoxy, for each optionally substituted by halogen substituted alkenylthio or alkynylthio each having 3 to 6 carbon atoms, for alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, or for in each case optionally by cyano , Halogen or CrC 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.

R5 preferably represents hydrogen, hydroxyl, amino, cyano, alkyl, alkoxy, alkoxycarbonyl or alkylamino, each optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, each having up to 6 carbon atoms, alkenyl optionally substituted by halogen or Alkynyl each having up 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 groups and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C 1 -C 4 haloalkyl, -C ₄ alkoxy or Cι-C ₄ haloalkoxy or phenyl-C ₁ -C ₄ alkyl.

Two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - optionally together preferably represent optionally substituted by halogen and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO2-, -NH- or -N (C ₁ -C -alkyl) - at the beginning (or at the end) or alkanediyl or alkenediyl interrupted within the hydrocarbon chain, each having 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.

A particularly preferably represents a single bond or the grouping C (R ² , R ³ ),

in which

R ^{2 represents} hydrogen, methyl, ethyl, n- or i-propyl, and

R ^{3 represents} hydrogen, methyl, ethyl, n- or i-propyl.

R ¹ particularly preferably represents in each case optionally substituted by cyano, formyl (CHO), fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoximino, ethoximino, methylthio, ethylthio, n- or i-propylthio

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally substituted by cyano, fluorine, chlorine or bromine, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl,

Cyclobutylmethyl, Cyclopentylmethyl or Cyclohexylmethyl, each optionally by nitro, amino, cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, Trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-

Propylthio, difluoromethylthio, trifluoromethylthio or chlorodifluoromethylthio substituted phenyl or benzyl, or for each optionally substituted by nitro, amino, cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl,

Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio or chlorodifluoromethylthio substituted heterocyclyl, thyl furyluryl, tolyl, tolyl, tolyl, tolyl, tolyl, tolyl, tolyl, tolyl, tolyl, tolyl, tolyl, tolyl, tolyl, tolyl, tol Oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, or

Heterocyclylalkyl from the series furyhnethyl, furylethyl, furyl- (n- or i -) - propyl, tetrahydrofurylmethyl, tetrahydrofurylethyl, tetrahydrofuryl- (n- or i -) - propyl, dioxolanylmethyl, dioxolanylethyl, dioxolanyl - (- or n propyl, pyridinyl ethyl, pyridinylethyl, pyridinyl- (n- or i-) propyl, pyrimidinylmethyl, pyrimidinylethyl, pyrimidinyl- (n- or i-) propyl.

X particularly preferably represents hydrogen, fluorine or chlorine.

Y particularly preferably represents O (oxygen), S (sulfur) or NH.

Z particularly preferably stands for

(Z ³ ) (Z ¹¹ ) (Z ¹³ ) R ⁴ particularly preferably represents hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for methyl, ethyl, n- or i, each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy -Propyl, n-, i-, s- or t-butyl, for ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine, for each optionally by cyano, fluorine, chlorine, methoxy or Ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for propenyloxy, 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, butenylthio, propynylthio or butinylthio optionally substituted by fluorine, chlorine or bromine, for methyl lamino, ethylamino, n- or i-propylamino, dimethyl-a ino or diethylamino, or for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl or cyclohexylmethyl.

R5 particularly preferably stands for hydrogen, hydroxyl, amino, cyano, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-substituted in each case optionally by cyano, fluorine, chlorine, bromine, methoxy or ethoxy -Butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, for ethenyl, propenyl optionally substituted by fluorine, chlorine or bromine, Butenyl, ethynyl, 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, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, di-fluoromethoxy, trifluoromethoxy or chlorodifluoromethoxy substituted phenyl or benzyl.

Two adjacent radicals - R ⁴ and R ⁴ , R ^ and ^ or R ⁴ and R ^ - optionally together preferably represent optionally substituted by fluorine and or chlorine and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO2-, -NH- or -N (methyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or

Alkenediyl, each with up to 4 carbon atoms.

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.

A very particularly preferably represents a single bond or the grouping C (R ² , R ³ ),

in which

R ^{2 represents} hydrogen or methyl, and

R ^{3 represents} hydrogen or methyl.

R ¹ very particularly preferably represents in each case optionally by cyano,

Formyl (CHO), fluorine, chlorine and / or bromine, methoximino or ethoxyimino substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for each optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butinyl, each optionally cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted by fluorine, chlorine, bromine, methyl or ethyl, or for each optionally by nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n-, or i-difluoromethyl Trifluoromethylthio or chlorodifluoromethylthio substituted phenyl or benzyl or for tetrahydrofurylmethyl optionally substituted by methyl.

Y very particularly preferably represents O (oxygen) or S (sulfur).

R ⁴ very particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s-, which are each optionally substituted by fluorine and / or chlorine. or t-butyl, for ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally substituted by fluorine and / or chlorine, for methoxy or ethoxy, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, for methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for each methylthio or ethylthio optionally substituted by fluorine and / or chlorine, or for cyclopropyl or cyclopropylmethyl each optionally substituted by fluorine, chlorine or methyl.

R5 very particularly preferably represents hydrogen, amino, methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine and or chlorine, propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine and / or chlorine, or by each if necessary cyclopropyl or cyclopropylmethyl substituted by fluorine, chlorine or methyl.

Two adjacent radicals - R ⁴ and R ⁴ , R ^ and R ^ or R ⁴ and R ^ - optionally together preferably represent optionally substituted by fluorine and / or chlorine and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO2-, -NH- or -N (methyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl, each with up to 4 carbon atoms.

Y ¹ very particularly preferably represents O (oxygen), S (sulfur), NH, N (methyl) or methylene.

Y ² very particularly preferably represents a single bond or O (oxygen), S (sulfur), NH or N (methyl).

Y and Y are different in each individual case.

The individual radicals R ⁴ and R ^ - 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.

A very particularly preferred group are those compounds of the formula (I) in which

represents a single bond or the grouping C (R, R), where

R ^{2 represents} hydrogen or methyl, and

R ^{3 represents} hydrogen or methyl, Q stands for O (oxygen),

R ¹ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine and / or bromine, for each optionally substituted by fluorine, chlorine, bromine, methyl or Ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or for each optionally by nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl , Trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-

Propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio or chlorodifluoromethylthio substituted phenyl,

X represents hydrogen, fluorine or chlorine,

Y stands for O (oxygen), and

Z stands for the heterocyclic grouping outlined below

in which

Q ^{1 represents} oxygen or sulfur (especially oxygen),

Q ^{2 represents} oxygen or sulfur (especially oxygen), R ^{4 "1 stands} for cyano, carbamoyl, thiocarbamoyl, or for methyl, ethyl, n- or i-propyl (in particular trifluoromethyl) which is optionally substituted by fluorine and / or chlorine,

R ^{4 "2 represents} hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl (in particular hydrogen, chlorine or methyl) which is optionally substituted by fluorine and / or chlorine, and

R ^{5 represents} hydrogen, amino, methyl, ethyl, n- or i-propyl, propenyl, propynyl, cyclopropyl or cyclopropylmethyl (in particular amino or methyl).

Another very particularly preferred group are those compounds of the formula (I) in which A, Q, R ¹ , X and Y have one of the meanings mentioned above, and

Z represents the heterocyclic grouping outlined below,

in which

Q ^{1 represents} oxygen or sulfur (especially oxygen),

Q ^{2 represents} oxygen or sulfur (especially oxygen), and

R ⁵ for hydrogen, for each methyl, ethyl, n- or i-propyl optionally substituted by fluorine and / or chlorine, for propenyl, butenyl, propynyl or butynyl optionally substituted by fluorine and / or chlorine, or for each optionally optionally substituted by fluorine , Chlorine or methyl substituted Cyclopropyl or cyclopropylmethyl (especially for methyl or difluoromethyl) is.

Another very particularly preferred group are those compounds of the formula (T) in which A, Q, R ¹ , X and Y have one of the meanings given above, and

Z represents the heterocyclic grouping outlined below,

in which

R ^{4 "1 represents} hydrogen, cyano, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl (in particular hydrogen, chlorine or bromine) substituted by fluorine and / or chlorine, and

R ^{4 "2 stands} for cyano or for methyl, ethyl, n- or i-propyl (in particular for trifluoromethyl) which is optionally substituted by fluorine and / or chlorine, and

R 5 stands for methyl, ethyl, n- or i-propyl (especially for methyl).

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

According to the invention, particular preference is given to those compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred. Those compounds of the formula (I) which have a combination of the meanings listed above as being very particularly preferred are very particularly preferred according to the invention.

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.

The new substituted benzo nitrogen heterocycles have interesting biological properties. They are particularly characterized by their strong herbicidal activity.

The new substituted benzo nitrogen heterocycles are obtained if benzo nitrogen heterocycles of the general formula (II)

in which

A, Q, X, Y and Z have the meaning given above,

with sulfenoic acid halides of the general formula (III)

in which R ^{1 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.

For example, if (7-fluoro-3-oxo-3,4-dihydro-2H-l, 4-benzoxazin-6-yl) - l, 2-dimethyl-l, 2,4-triazolidin-3,5-dione is used and fluorodichloromethanesulfonic acid 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 benzo nitrogen heterocycles to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (II), Q, X, Y and Z preferably have those meanings which are already preferred above, in connection with the description of the compounds of the general formula (I) according to the invention, particularly preferred or very particularly preferred for Q, X, Y and Z have been specified.

The starting materials of the general formula (II) are known and or can be prepared by processes known per se (cf. EP-A-170191, EP-A-311135, EP-A-328 001, EP-A-360 072, EP -A-379 894, EP-A-408 382, EP-A-415 642, EP-A-454444, EP-A-488 220, EP-A-568 041, US-A-4755 217, US-A -4 761 174, US-A-5 084 084, US-A-5 281 571, WO-A-90/10626, WO-A-92/06962, WO-A-97/26248, WO-A-97 / 28127, WO-A-98/07720, WO-A-99/59983). Formula (HI) provides a general definition of the sulfenoic 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 (ILT), R ¹ preferably has the meaning which has already been given as preferred, particularly preferred or very particularly preferred for R ¹ in connection with the description of the compounds of the general formula) according to the invention. X ¹ preferably represents fluorine, chlorine or bromine, especially chlorine.

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

The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using a reaction auxiliary. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. These preferably include 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; basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl- benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5-ethyl-2-methylpyridine, 4-dimethylamino-pyridine, N-methylpiperidine, 1,4-diazabicyclo [2.2.2] - octane (DABCO), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1.8 diazäbicyclo [5.4.0] undec-7-ene (DBU).

The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using a diluent. Inert organic solvents are particularly suitable as diluents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, 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-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide.

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, 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. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a large excess. The reaction is generally carried out in a suitable diluent in the presence a reaction auxiliary and the reaction mixture is generally stirred for several hours at the required temperature. Working up is carried out according to customary methods (cf. the production examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular 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 depends essentially on the amount used.

The active compounds according to the invention can e.g. can be used in the following plants:

Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea,

Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Plantaago, Pharb 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, Pisu, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus,

Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus,

Dactyloctenium, Digitaria, Echinochloa, Eleochans, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, 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.

Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover. The active compounds according to the invention for weed control in permanent crops, e.g. Forest, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa,

Berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective weed control in annual crops.

The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.

The active compounds according to the invention can be used in certain concentrations or

Application rates can also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds. According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of the plants, such as sprout, leaf, flower and root, examples being leaves,

Needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes are listed. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild plants (weeds, harmful plants) and / or by conventional organic breeding methods, such as e.g. Crossing or protoplast fusion, preserved plant species and plant varieties (crop plants) and their parts treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms) and their parts are treated. The term "parts" or "parts of plants" or "plant parts" was explained above.

Plant varieties are cultivated plants with certain properties (“traits”) which have been obtained both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes. The transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or water salt or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients. Examples of transgenic plants are the important crop plants such as cereals (including rice), maize, soybeans, potatoes, cotton, beets, rapeseed, cultivated grasses such as golf and ornamental turf, fruit plants (with the fruits apples, pears, citrus fruits and grapes) and Plantation crops such as oil and rubber trees are mentioned, with cereals (including rice), corn, soybeans, potatoes, cotton, beets and rapeseed being particularly emphasized. The traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringjensis (for example by the genes CryΙA (a), CryIA (b), CryIA (c), CryllA, CrylHA, CryiπB2, Cry9c, Cry2Ab, Cry3Bb and CryLF as well as their combinations) are produced in the plants (hereinafter "Bt plants"). The traits that are particularly emphasized are the elevated ones

Defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins. The traits are also particularly emphasized as the increased tolerance of the plants to certain herbicidal active substances and classes of active substances such as glyphosate or glufosinate / phosphinothricin (eg "PAT" gene), ALS materials such as imida- zolinones, sulfonylureas and others, PPO inhibitors (eg plants with acuron genes), 4-HPD inhibitors such as isoxazoles (eg isoxaflutole), ACCase inhibitors such as sethoxydim, and bromoxynil.

The genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).

Examples of herbicide-tolerant plants are maize varieties, cotton varieties, soy varieties, cereals including rice varieties, beet varieties and rapeseed varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosates e.g. corn, cotton, soybean, beet, rapeseed), Liberty Link® (tolerance against glufosinates, eg rapeseed, maize, beets), IMI® (tolerance against imidazolinones) and STS® (tolerance against sulfonylureas eg maize). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (e.g. maize, rice).

Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also cause superadditive ("synergistic") effects. For example, reduced application rates and / or widening of the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention - also in combination with other agrochemicals

Active ingredients -, better plant growth of crops, increased tolerance of Crop plants against high or low temperatures, increased tolerance of the crop plants to dryness or to water salt or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of harvested products possible that go beyond the expected effects.

The plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active compound mixtures according to the invention, in addition to the good control of the

Weed plants have the above-mentioned synergistic effects with the plants or plant cultivars described above. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.

The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.

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

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as 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.

Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,

Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Ligmn sulfite liquor and

Methylcellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho- lipids such as cephalins and lecithins and synthetic phospholipids. Other additives can 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 can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known herbicides and / or with substances which improve crop plant tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible Mixtures with weed control agents are also possible which contain one or more 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), Benulfureson -methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxime,

Bromoxynil, Butachlor, Butafenacil (-allyl), Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlorodoluron-Cin ), Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Clor-ansulam (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosate Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichlorprop (-P), Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, 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, Fiumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flurpyrsulfuron

(-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-butoxypropyl, -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Foramsulfuron, Glufosinate (-ammonium), Glyphosate ( isopropylammonium), halosafen, haloxyfop (-ethoxyethyl, -P-methyl), hexazinones, imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, hnazaquin, imazethapyr,

Imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacamlor, methonazuriton, methronione, mesotrione , Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Napro-anilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzaline, Oxadiazon, Oxadiazon, Oxadiazon, Oxadiazon, Oxadiazon, Oxadiazon, Oxadiaronon , Oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron (-methyl), profluazole, prometryn, propachlor, propanil, propaquizafop, propisochlorz, propoxycarbazone (

Prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinchlorac oclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron, sethoxydim, Simazine, Simetryn, Sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxynine, then terbuthylazine, terbuthylazine, terbuthylazine . Thiafluamides, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), triclopyr, tri-diphane, trifluralin, trifloxysulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron, trifitosulfuron, trifitlusulfuron, trifitosulfuron, trifitosulfuron.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil stain remedies, is also possible.

The active ingredients as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use

Solutions, suspensions, emulsions, powders, pastes and granules are used. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends 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, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below. Herstellungsbeispieϊe:

example 1

To a solution of 0.54 g (1.5 mmol) of 3- (7-fluoro-3,4-dihydro-3-oxo-2H-l, 4-benz-oxazin-6-yl) -l-methyl- 6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione in 13 ml dichloromethane are added in succession at room temperature (approx. 20 ° C) 0.26 ml (3.3 mmol) pyridine and 0.5 g ( 2.8 mmol) 1,1-difluoro-ethanesulfonic acid chloride. The reaction mixture is stirred at room temperature for 18 hours, then with

Diluted 15 ml dichloromethane and washed successively with 2N hydrochloric acid, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride solution, dried over magnesium sulfate and largely freed from the solvent under reduced pressure. The crude product thus obtained is purified by column chromatography over silica gel with dichloromethane as the eluent.

0.45 g (66% of theory) of 3- [7-fluoro-3,4-dihydro-3-oxo-4- (l, l-difluoroethylthio) -2H-l, 4-benzoxazin-6 are obtained -yl] -l-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione.

LogP (at pH = 2.3): 2.69. Example 2

To a solution of 2.0 g (5.7 mmol) of 6- (4-chloro-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl) -7-fluoro-2H-1, 4-benzoxazin- 3 (4H) -one in 15 ml of tetrahydrofuran is added to 0.3 g (7.5 mmol) of 60% nafriunmydrid in paraffin oil. The mixture is stirred for approx. 60 minutes at room temperature (approx. 20 ° C) and then cooled to -35 ° C. To the cooled solution is added a solution of isopropanesulfenyl chloride prepared from 0.47 g (3.1 mmol) of diisopropyl disulfide, 0.25 ml (3.1 mmol) of sulfuryl chloride and 10 ml of tetrahydrofuran at -30 ° C. After 20 min. Reaction time in which the reaction temperature rises to -8 ° C, the reaction mixture is mixed with 30 ml of ethyl acetate, washed successively with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent is largely removed under reduced pressure and the crude product thus obtained is purified by column chromatography on silica gel using dichloromethane as the eluent.

1.85 g (76% of theory) of 6- (4-chloro-l-methyl-5-trifluoromethyl-1H-ρyrazol-3-yl) -7-fluoro-4- (2-isopropylthio) -2H are obtained -l, 4-benzoxazin-3 (4H) -one.

LogP (at pH = 2.3): 4.18.

Analogously to Examples 1 and 2 and in accordance with the general description of the production process according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Table 1 below.

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

The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal 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 ^D ). The calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP value based on the retention times by linear interpolation between two successive alkanones).

The lambda maximums were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.

Application examples:

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The concentration of active ingredient in the spray liquor is selected so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.

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 destruction

In this test, for example, the compounds according to preparation example 1, 2, 3, 4, 5, 6, 7, 8, 13, 14, 15, 16, 17, 18 and 28 show, in some cases, good tolerance to crop plants, such as, for example, maize, Wheat and soy, very effective against weeds. Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired level

Concentration.

Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 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 destruction

In this test, for example, the compounds according to the preparation example show

1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 and 28 with good tolerance to crops, such as e.g. Wheat, very effective against weeds.

Claims

Patentansprtiche

1. Compounds of formula (I)

in which

represents a single bond or the grouping C (R, R),

in which

represents hydrogen or alkyl, and

R ^{3 represents} hydrogen or alkyl,

Q represents O (oxygen) or S (sulfur),

R ¹ represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,

X represents hydrogen or halogen,

Y represents O (oxygen), S (sulfur), NH or NR ¹ , and

represents one of the heterocyclic groupings outlined below

(z ¹ ) (z ² ) (?)

(z ⁴ ) (Z ⁵ ) (Z ⁶ )

(z ⁷ ) (Z ^ö ) (Z ⁹ )

(z ²² ) (z ²³ ) (z ²⁴ )

(z ²⁸ ) (z ²⁹ ) (z ³⁰ )

(z ³⁴ ) (z ³⁵ ) (z ³⁶ )

(z ³⁷ ) (z ³⁸ ) (z ³⁹ )

(z ⁴⁰ ) (z ⁴¹ ) (z ⁴² )

(Z ⁴³ ) (z ⁴⁴ ) (z ⁴⁵ )

(z ⁴⁶ ) (z ⁴⁷ ) (z ⁴⁸ )

(z ⁴⁹ ) (z ⁵⁰ ) (z ⁵¹ )

(z ⁵² ) (z ⁵³ )

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, dialkyl amino, cycloalkyl or cycloalkylalkyl, R ^ represents hydrogen, hydroxy, amino, cyano, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl,

where optionally two adjacent radicals - R ⁴ and R ⁴ , R ^ and R5 or R ⁴ and R ^ - together for optionally substituted and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO- , SO2-, -NH- or -N (alkyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl,

Y ^{1 represents} O (oxygen), S (sulfur), SO, SO ₂ , NH, N (alkyl) or methylene, and

Y 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

A represents a single bond or the grouping C (R ² , R ³ ),

in which

R ^{2 represents} hydrogen or alkyl having 1 to 6 carbon atoms, and R ^{3 represents} hydrogen or alkyl having 1 to 6 carbon atoms,

Q stands for O (oxygen),

R ¹ for alkyl optionally substituted by cyano, formyl (CHO), halogen, C ₁ -C ₄ -alkoxy, Cr -alkoximino or C1-C4-alkylthio, each having alkenyl or alkynyl which is optionally substituted by cyano or halogen each having 2 to 6 carbon atoms, each optionally by cyano,

Halogen or - -alkyl substituted cycloalkyl or cycloalkylalkyl, each with 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, amino, cyano, carboxy, carbamoyl, halogen, C ₁ -C ₄ Alkyl, CrC ₄ haloalkyl, C ₁ -C ₄ alkoxy,

C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio or Cr haloallylthio 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 nitro, amino, Cyano, carboxy, carbamoyl, halogen, Cr -alkyl, C ₁ -C ₄ -

Haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C haloalkoxy, C1-C ₄ -alkylthio or CrCi-haloalkylthio substituted heterocyclyl or heterocyclylalkyl each having 1 to 6 carbon atoms, optionally up to 4 nitrogen atoms and optionally up to 2 oxygen atoms or sulfur atoms in the heterocyclyl group and optionally up to

4 carbon atoms in the alkyl part,

X represents hydrogen, fluorine, chlorine or bromine,

Y represents O (oxygen), S (sulfur), NH, N-CH ₃ or NC ₂ H ₅ , and Z represents one of the heterocyclic groupings outlined below,

(Z ¹² ) (Z ¹³ ) (z ⁵² )

in which

Q ^{1 stands} for O (oxygen),

Q ^{2 stands} for O (oxygen),

R ⁴ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, for optionally by cyano, halogen or

C ₁ -C ₄ alkoxy substituted alkyl having 1 to 6 carbon atoms, each for alkenyl or alkynyl optionally substituted by halogen or each having 2 to 6 carbon atoms, each for alkoxy or alkoxycarbonyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy with 1 to 6 carbon atoms in each

Alkyl groups, each for alkenyloxy or alkynyloxy 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 Ci-Gralkoxy, 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 represents cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or -C4-alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part,

for hydrogen, hydroxyl, 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 optionally substituted by halogen each with up to 6 carbon atoms, each optionally by cyano, halogen or

Substituted cycloalkyl or cycloalkylalkyl, each with 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally with nitro, cyano, halogen, C 8 alkyl, CrC -haloalkyl, C ₁ -C ₄ -

Alkoxy or C ₁ -C -haloalkoxy substituted phenyl or phenyl-C ₁ -C ₄ -alkyl,

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-, SO2-, -NH- or -N (Cι- C alkyl) - at the beginning (or at the end) or within the hydrocarbon chain there are interrupted alkanediyl or alkenediyl, each having up to 5 carbon atoms, Y ^{1 represents} O (oxygen), S (sulfur), SO, SO ₂ , NH, N (dC ₄ -alkyl) or methylene, and

Y ^{2 represents} a single bond or O (oxygen), S (sulfur), SO, SO ₂ , NH or N Cr alkyl).

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

A represents a single bond or the grouping C (R ² , R ³ ),

in which

R represents hydrogen, methyl, ethyl, n- or i-propyl, and

R ^{3 represents} hydrogen, methyl, ethyl, n- or i-propyl,

R ¹ for each optionally substituted by cyano, formyl (CHO), fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoximino, ethoximino, methylthio, ethylthio, n- or i-propylthio

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally substituted by cyano, fluorine, chlorine or bromine, for each cyclopropyl, cyclobutyl, cyclopentyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl,

Cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, for each optionally by nitro, amino, cyano, carboxy, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl,

Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoro- methoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio or chlorodifluoromethylthio substituted phenyl or benzyl, or for each optionally substituted by nitro, amino, cyano, carboxy, carbamoyl, methyl, chlorine, chlorine, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethyl , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthiσ or chlorodifluoromethylthio substituted heterocyclyl from the series furyl, tetrahydrofuryl, thienyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, methylidyl, methyltriazylyl, methylidyl, methyltriazylyl, methylidyl, methyldiazylyl, methylidyl, methyldiazylyl, methylidyl, trifluoromethyl, from methyl , Furyl- (n- or i -) - ρropyl, tetrahydrofurylmethyl, tetrahydrofurylethyl, tetrahydrofuryl- (n- or i -) - propyl, dioxolanyl- m ethyl, dioxolanylethyl, dioxolanyl- (n- or i -) - propyl, pyridinyl-methyl, pyridinylethyl, pyridinyl- (n- or i -) - propyl, pyrimidinyl-methyl, pyrimidinylethyl, pyrhnidinyl- (n- or i -) - propyl stands,

X represents hydrogen, fluorine or chlorine,

Y represents O (oxygen), S (sulfur) or NH, and

For

(z ³ ) (z ¹¹ ) (z ¹³ )

stands, where R ⁴ for hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, n-, i-, s- or t-butyl, for ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine, for methoxy, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for each optionally by

Fluorine, chlorine or bromine substituted propenyloxy, butenyloxy, propynyloxy or butynyloxy, each for methylthio, ethylthio, n- or i-propylthio optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, each optionally substituted by fluorine, chlorine or bromine substituted propenylthio, butenylthio, propynylthio or butynylthio, for methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, or for cyclopropyl, cyclobutyl, cyclopentyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, Cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,

R5 for hydrogen, hydroxy, amino, cyano, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, methoxy,

Ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, for each optionally substituted by fluorine, chlorine or bromine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butinyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, which are optionally substituted by cyano, fluorine, chlorine, bromine, methyl or ethyl, Cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl , Dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, di-fluoromethoxy, trifluoromethoxy or chlorodifluoromethoxy substituted phenyl or benzyl,

two adjacent radicals - R ⁴ and R ⁴ , R ⁵ and R ⁵ or R ⁴ and R ⁵ - optionally together for optionally by fluorine and / or

Chlorine substituted and / or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO2-, -NH- or -N (methyl) - at the beginning (or at the end) or within the Hydrocarbon chain interrupted alkanediyl or alkenediyl each having up to 4 carbon atoms,

Y ^{1 represents} O (oxygen), S (sulfur), SO, SO ₂ , NH, N (methyl) or methylene, and

Y ² for a single bond or for O (oxygen), S (sulfur), SO,

SO ₂ , NH or N (methyl) is.

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

represents a single bond or the grouping C (R, R> 3 ^> ),

in which

R ^{z represents} hydrogen or methyl, and R ^{3 represents} hydrogen or methyl,

R ¹ for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, formyl (CHO), fluorine, chlorine and or bromine, methoximino or ethoxyimino, for each Ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, optionally substituted by fluorine, chlorine or bromine, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, or in each case optionally by nitro , Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-Propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio or chlorodifluoromethylthio substituted phenyl or benzyl or for tetrahydrofurylmethyl optionally substituted by methyl stands,

represents O (oxygen) or S (sulfur),

R ⁴ for hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine and / or chlorine , for each optionally substituted by fluorine and / or chlorine, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, for each methoxy or ethoxy optionally substituted by fluorine, chlorine, methoxy or ethoxy, for methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl , for each methylthio or ethylthio optionally substituted by fluorine and / or chlorine, or for each optionally substituted by fluorine, chlorine or methyl

Cyclopropyl or cyclopropylmethyl, R ^ for hydrogen, amino, for each optionally ^' substituted by fluorine and / or chlorine methyl, ethyl, n- or i-propyl, for each optionally substituted by fluorine and / or chlorine propenyl, butenyl, propynyl or butynyl, or represents in each case optionally substituted by fluorine, chlorine or methyl cyclopropyl or cyclopropylmethyl,

two adjacent radicals - R ⁴ and R ⁴ , R ^ and R ^ or R ⁴ and R ^ - optionally together for optionally by fluorine and or

Chlorine substituted and or optionally by O (oxygen), S (sulfur) or a group from the series -SO-, SO2-, -NH- or -N (methyl) - at the beginning (or at the end) or within the hydrocarbon chain interrupted alkanediyl or alkenediyl each having up to 4 carbon atoms,

Y ^{1 represents} O (oxygen), S (sulfur), NH, N (methyl) or methylene, and

Y preferably represents a single bond or O (oxygen), S (sulfur), NH or N (methyl).

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

A stands for a single bond or the grouping C (R ² , R ³ ), where

R ^{2 represents} hydrogen or methyl, and

R ^{3 represents} hydrogen or methyl, Q stands for O (oxygen),

R ¹ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine and / or bromine, for each optionally substituted by fluorine, chlorine, bromine, methyl or Ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or for each optionally by nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl , Trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethyl, trifluoromethyl, trifluoromethyl

X represents hydrogen, fluorine or chlorine,

Y stands for O (oxygen), and

Z stands for the heterocyclic grouping outlined below

in which

Q ^{1 represents} oxygen or sulfur (especially oxygen),

Q ^{2 represents} oxygen or sulfur (especially oxygen), R ^{4 "1 stands} for cyano, carbamoyl, thiocarbamoyl, or for methyl, ethyl, n- or i-propyl (in particular trifluoromethyl) which is optionally substituted by fluorine and / or chlorine,

R ^{4 "2 represents} hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl (in particular hydrogen, chlorine or methyl) which is optionally substituted by fluorine and / or chlorine, and

R ^{5 represents} hydrogen, amino, methyl, ethyl, n- or i-propyl, propenyl, propynyl, cyclopropyl or cyclopropylmethyl (in particular amino or methyl).

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

represents the heterocyclic grouping outlined below,

in which

Q ^{1 represents} oxygen or sulfur (especially oxygen),

Q ^{2 represents} oxygen or sulfur (especially oxygen), and

R ⁵ for hydrogen, for in each case optionally substituted by fluorine and / or chlorine methyl, ethyl, n- or i-propyl, for in each case optionally substituted by fluorine and / or chlorine propenyl, butenyl, propynyl or butynyl, or for in each case optionally by Fluorine, chlorine or methyl substituted cyclopropyl or cyclopropylmethyl (especially for methyl or difluoromethyl).

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

Z represents the heterocyclic grouping outlined below,

in which

R ^{4 "1 represents} hydrogen, cyano, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl (in particular hydrogen, chlorine or bromine) substituted by fluorine and / or chlorine, and

R ^{4 "2 stands} for cyano or for methyl, ethyl, n- or i-propyl (in particular for trifluoromethyl) which is optionally substituted by fluorine and / or chlorine, and

R ^{5 represents} methyl, ethyl, n- or i-propyl (especially methyl).

Process for the preparation of compounds of the formula (I) according to Claim 1, characterized in that benzo nitrogen heterocycles of the general formula (II)

in which

A, Q, X, Y and Z have the meaning given in claim 1,

with sulfenoic acid halides of the general formula (III)

X ^ SR ¹ (in)

in which

R ^{1 has} the meaning given in claim 1 and

X ^{1 represents} halogen,

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

9. Herbicidal agent, characterized by a content of at least one compound of the formula (I) according to spoke 1 and conventional extenders.

10. Use of at least one compound of formula (I) according to claim 1 for controlling unwanted plants.

11. A method for combating undesirable plants, characterized in that at least one compound of the formula (I) according to

Claim 1 or a herbicidal composition according to claim 9 can act on undesirable plants and / or their habitat.