DE102008006005A1 - New N-azinyl-N'-pyridylsulfonyl-urea compounds useful e.g. as herbicide, plant growth regulator and plant protection regulator and to combat undesirable plant growth e.g. Agrostis in special plant cultures e.g. wheat, barley and rye - Google Patents

Abstract

N-Azinyl-N'-pyridylsulfonyl-urea compounds (I) and their salts are new. N-Azinyl-N'-pyridylsulfonyl-urea compounds of formula (I) and their salts are new. V 1>, W 1>, X, Y 1>N or C (both optionally substituted by R 8>); A : N or CR 9>; R 9>H (preferred), alkyl, halo or haloalkyl; R 1>H, alkyl, alkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl or aryl; R 2>, R 3>alkyl, alkoxy, alkylthio, alkyl amino or dialkylamino (all optionally halo substituted), H or halo; R 4>-R 7>H, halo, CN, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl (where R 4>and R6, and/or R 5>and R 7>is an alkylidene group optionally interrupted by O or S); R 8>H, halo, CN, thiocyanato, nitro, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkyl amino, dialkylamino, alkyl carbonyl, alkoxycarbonyl, alkylaminocarbonyl, or dialkylaminocarbonyl; and Q : O or S. Where one of the residue of V 1>, W 1>, X, Y 1>is N and the remaining residues are C. Independent claims are included for: (1) a (4,5-dihydroisoxazol-3-yl) sulfonamide compound of formula (II); (2) a (4,5-dihydroisoxazol-3-yl) sulfonic acid halide compound of formula (VIII); (3) a (4,5-dihydroisoxazol-3-yl) halide compound of formula (XI); (4) a (4,5-dihydroisoxazol-3-yl) thiol compound of formula (X); and (5) the preparation of (I). Hal : halogen atom. [Image] [Image] [Image] ACTIVITY : Herbicide; Plant Growth Regulant. The herbicidal activity of (I) was tested against Alopecurus myosuroides. The results showed that N-[(4-chloro-6-methoxy-pyrimidin-2-yl)carbamoyl]-3-(4,5-dihydroisoxazol-3-yl)-pyridin-2-sulfonamide exhibited an aborticide effectof 100%. MECHANISM OF ACTION : None given.

Description

The The present invention relates to N-azinyl-N'-pyridylsulfonylureas. Another object of the present invention are mixtures of previously mentioned urea derivatives with other herbicides and / or Safeners. Moreover, the present invention relates Process for the preparation of the aforementioned urea derivatives and the use of these compounds as herbicides and plant growth regulators alone and in mixture with safeners and / or in mixture with others Herbicides, in particular their use for plant control in special crops or as plant protection regulators.

It is already known that certain N-azinyl-N'-arylsulfonylureas with simple open-chain hydroxamic acid ester groups in the aryl moiety such. B. N- (4,6-dimethylpyrimidin-2-yl) -N '- (2-methoxyaminocarbonyl-phenylsulfonyl) urea and the corresponding N' - (2-n-Octyloxyaminocarbonylphenylsulfonyl) urea have herbicidal properties (see. DE 3 516 435 A . EP 0 173 958 A . US 4,704,158 ).

Furthermore, certain herbicidally active N-azinyl-N'-hetarylsulfonylureas are known which are substituted in the hetaryl by O, N-dialkylated, also open-chain hydroxamic acid groups (see. EP 0 301 784 A ); corresponding cyclic hydroxamic acid derivatives, however, have not previously been described.

• (a) dass sie keine oder aber eine nur unzureichende herbizide Wirkung gegen Schadpflanzen besitzen,
• (b) dass nur ein zu geringes Spektrum an Schadpflanzen, bekämpft werden kann, oder
• (c) dass sie eine zu geringe Selektivität in Nutzpflanzenkulturen besitzen.

The active substances already known according to the abovementioned publications have disadvantages in their application, whether it be

• (a) they have no or only insufficient herbicidal activity against harmful plants,
• (b) that only too low a range of harmful plants can be controlled, or
• (c) that they have too low a selectivity in crops.

It is therefore desirable alternative chemical agents to provide on the basis of corresponding urea derivatives, which are used as herbicides or plant growth regulators can and with what certain advantages in comparison are connected to known from the prior art systems.

In order to generally results in the object of the present invention, to provide corresponding alternative urea derivatives which as herbicides or plant growth regulators, in particular with a satisfactory herbicidal action against harmful plants, with a broad spectrum against harmful plants and / or with a high selectivity in crops can be. These urea derivatives should preferably a better property profile, especially a better herbicidal Action against harmful plants, a wider range Harmful plants and / or higher selectivity in crops, as known from the prior art Show urea derivatives.

in welcher
V, W, X und Y so gewählt werden, dass eine dieser Indizes für Stickstoff steht und die übrigen Indizes für Kohlenstoffatome stehen, welche unsubstituiert oder aber mit dem dargestellten Rest R⁸ substituiert sein können;
A ausgewählt ist aus der Gruppe, bestehend aus Stickstoff und CR⁹;
wobei
R⁹ ausgewählt ist aus der Gruppe, bestehend aus Wasserstoff, Alkyl, Halogen und Haloalkyl;
R¹ ausgewählt ist aus der Gruppe, bestehend aus Wasserstoff und einem gegebenenfalls substituierten Rest aus der Reihe Alkyl, Alkoxy, Alkoxyalkyl, Alkenyl, Alkinyl, Cycloalkyl, Cycloalkylalkyl, Aralkyl und Aryl;
R² ausgewählt ist aus der Gruppe, bestehend aus Wasserstoff, Halogen, gegebenenfalls durch Halogen substituiertes Alkyl, gegebenenfalls durch Halogen substituiertes Alkoxy, gegebenenfalls durch Halogen substituiertes Alkylthio, gegebenenfalls durch Halogen substituiertes Alkylamino oder gegebenenfalls durch Halogen substituiertes Dialkylamino;
R³ ausgewählt ist aus der Gruppe, bestehend aus Wasserstoff, Halogen, gegebenenfalls durch Halogen substituiertes Alkyl, gegebenenfalls durch Halogen substituiertes Alkoxy, gegebenenfalls durch Halogen substituiertes Alkylthio, gegebenenfalls durch Halogen substituiertes Alkylamino oder gegebenenfalls durch Halogen substituiertes Dialkylamino,
R⁴ bis R⁷, jeweils unabhängig voneinander, ausgewählt werden aus der Gruppe, bestehend aus Wasserstoff, Halogen, Cyano, Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino, Alkylcarbonyl, Alkoxycarbonyl, Alkylaminocarbonyl oder Dialkylaminocarbonyl, wobei die Reste unsubstituiert sein können oder ein oder mehrere Reste, ausgewählt aus der Gruppe, bestehend aus Halogen, Cyano, Alkoxy und Alkylthio, tragen können, oder R⁴ und R⁶ bzw. R⁵ und R⁷ eine gegebenenfalls durch Sauerstoff oder Schwefel unterbrochene Alkyliden-Gruppe darstellen,
R⁸ ausgewählt ist aus der Gruppe, bestehend aus Wasserstoff, Halogen, Cyano, Thiocyanato, Nitro, Alkyl, Alkoxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, Alkylamino, Dialkylamino, Alkylcarbonyl, Alkoxycarbonyl, Alkylaminocarbonyl, oder Dialkylaminocarbonyl, wobei die Reste unsubstituiert sein können oder ein oder mehrere Reste, ausgewählt aus der Gruppe, bestehend aus Halogen, Cyano, Alkoxy und Alkylthio, tragen können.
Q ausgewählt ist aus der Gruppe, bestehend aus Sauerstoff oder Schwefel, insbesondere Sauerstoff ist,
sowie Salze von Verbindungen der Formel (I).There have now been new N-azinyl-N'-pyridylsulfonylureas of the general formula (I),

in which
V, W, X and Y are chosen such that one of these indices is nitrogen and the remaining indices are carbon atoms which may be unsubstituted or substituted with the represented R ⁸ ;
A is selected from the group consisting of nitrogen and CR ⁹ ;
in which
R ^{9 is} selected from the group consisting of hydrogen, alkyl, halo and haloalkyl;
R ^{1 is} selected from the group consisting of hydrogen and an optionally substituted radical selected from alkyl, alkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl and aryl;
R ^{2 is} selected from the group consisting of hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy, optionally substituted by halogen alkylthio, optionally substituted by halogen alkylamino or optionally substituted by halogen dialkylamino;
R ³ is selected from the group consisting of hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy, optionally halogen-substituted alkylthio, optionally halogen-substituted alkylamino or dialkylamino optionally substituted by halogen,
R ⁴ to R ⁷ , each independently, are selected from the group consisting of hydrogen, halogen, cyano, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, the radicals being unsubstituted may be or may carry one or more radicals selected from the group consisting of halogen, cyano, alkoxy and alkylthio, or R ⁴ and R ⁶ or R ⁵ and R ^{7 represent} an optionally interrupted by oxygen or sulfur alkylidene group .
R ^{8 is} selected from the group consisting of hydrogen, halogen, cyano, thiocyanato, nitro, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, or dialkylaminocarbonyl, where the radicals may be unsubstituted or one or more radicals selected from the group consisting of halogen, cyano, alkoxy and alkylthio, can carry.
Q is selected from the group consisting of oxygen or sulfur, in particular oxygen,
and salts of compounds of the formula (I).

A first embodiment of the present invention comprises compounds of the general formula (I) in which
A is preferably selected from the group consisting of nitrogen and CH.

A second embodiment of the present invention comprises compounds of the general formula (I) in which
R ^{1 is} preferably selected from the group consisting of hydrogen, alkyl, alkoxy, alkoxyalkyl, alkenyl and alkynyl, where the radicals may be unsubstituted or may carry one or more halogen atoms,
R ^{1 is} particularly preferably selected from the group consisting of hydrogen, methyl, ethyl, methoxy, methoxymethyl and ethoxy,
R ^{1 is} particularly preferably selected from the group consisting of hydrogen and methyl,
and
R ^{1 is} particularly preferably hydrogen.

A third embodiment of the present invention comprises compounds of the general formula (I) in which
R ^{2 is} preferably selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, alkylthio, alkylamino and dialkylamino, where the radicals may be unsubstituted or may carry one or more halogen atoms,
R ^{2 is} particularly preferably selected from the group consisting of hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoroethoxy, difluoromethoxy, methylthio, methylamino and dimethylamino,
and
R ^{2 is} particularly preferably selected from the group consisting of hydrogen, chlorine, methyl, methoxy, methylthio and dimethylamino.

A fourth embodiment of the present invention comprises compounds of the general formula (I) in which
R ^{3 is} preferably selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, alkylthio, alkylamino and dialkylamino, where the radicals may be unsubstituted or may carry one or more halogen atoms,
R ^{3 is} particularly preferably selected from the group consisting of hydrogen, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoroethoxy, difluoromethoxy, methylthio, methylamino or dimethylamino
and
R ^{3 is} particularly preferably selected from the group consisting of methyl, methoxy and trifluoroethoxy.

A fifth embodiment of the present invention comprises compounds of the general formula (I) in which
R ⁴ to R ⁷ , each independently, are preferably selected from the group consisting of hydrogen, halogen, cyano, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl; or dialkylamino, where the radicals may be unsubstituted or may carry one or more halogen atoms,
R ⁴ to R ⁷ , each independently, are particularly preferably selected from the group consisting of hydrogen, fluorine, chlorine, cyano, methyl, ethyl, propyl, isopropyl, cyclopropyl, n-, i- s- or tert. Butyl, methylthio, methylsulfinyl, methylsulfonyl, methoxycarbonyl and ethoxycarbonyl, where the radicals may be unsubstituted or may carry one or more halogen atoms, and R ⁴ and R ⁶ or R ⁵ and R ^{7 is} a CH ₂ -CH ₂ -CH ₂ group , a CH ₂ -CH ₂ -CH ₂ -CH ₂ group, a CH ₂ -O-CH ₂ group, CH ₂ -S-CH ₂ group, a CH ₂ -O-CH ₂ -CH ₂ group , a CH ₂ -CH ₂ -O-CH ₂ group or CH ₂ -CH ₂ -O-CH ₂ -CH ₂ group,
and
R ⁴ to R ⁷ , in each case independently of one another, are particularly preferably selected from the group consisting of hydrogen, methyl, ethyl, propyl and isopropyl, or R ⁴ and R ⁶ or R ⁵ and R ^{7 is} a CH ₂ -CH ₂ - CH ₂ -group, a CH ₂ -CH ₂ -CH ₂ -CH ₂ -group, a CH ₂ -O-CH ₂ -group, CH ₂ -S-CH ₂ -group, a CH ₂ -O-CH ₂ - CH ₂ group, a CH ₂ -CH ₂ -O-CH ₂ group or CH ₂ -CH ₂ -O-CH ₂ -CH ₂ group represent.

A sixth embodiment of the present invention comprises compounds of the general formula (I) in which
R ^{8 is} preferably selected from the group consisting of hydrogen, halogen, cyano, thiocyanato, nitro, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl and dialkylaminocarbonyl, where the radicals may be unsubstituted or can carry one or more halogen atoms,
R ^{8 is} particularly preferably selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino and dimethylamino, where the radicals are unsubstituted may be or may carry one or more halogen atoms,
and
R ^{8 is} particularly preferably hydrogen.

Within the scope of these embodiments of the present invention, it is possible to arbitrarily combine the individual general, preferred and particularly preferred meanings for the substituents R ¹ to R ⁸ , Q and A. That is, compounds of the general formula (I) are encompassed by the present invention in which, for example, the substituent R ^{1 has} a preferred meaning and the substituents R ² to R ^{8 have} the general meaning or, for example, the substituent R ^{2 is} a preferred one Substituent R ^{3 has} a particularly preferred meaning, which and the other substituents have the general meaning. These individual combinations are not expressis verbis called for clarity, but are included within the scope of the present invention.

weist ein Stickstoffatom auf, d. h. ein Rest, ausgewählt aus der Gruppe, bestehend aus V, W, X und Y, entspricht einem Stickstoffatom. Die übrigen drei Reste weisen die Bedeutung eines Kohlenstoffatoms auf, wobei die Kohlenstoffatome gegebenenfalls mit dem Rest R⁸ substituiert sein können.The heterocycle of compounds of the general formula (I) directly connected to the dihydroisoxazole ring

has a nitrogen atom, ie, a group selected from the group consisting of V, W, X and Y, corresponds to a nitrogen atom. The remaining three radicals have the meaning of a carbon atom, wherein the carbon atoms may optionally be substituted by the radical R ⁸ .

In a particular embodiment of the present invention, the compound of the general formula (I) therefore has the following structure (Ia) in which V has the meaning of a nitrogen atom:

In a still further embodiment of the present invention, the compound of the general formula (I) therefore has the following structure (Ib), in which W has the meaning of a nitrogen atom:

In a still further embodiment of the present invention, the compound of the general formula (I) therefore has the following structure (Ic) in which X has the meaning of a nitrogen atom:

In a still further embodiment of the present invention, the compound of the general formula (I) therefore has the following structure (Id), in which Y has the meaning of a nitrogen atom:

In each of these four embodiments, the individual radicals R ¹ to R ⁸ , A and Q may have the general, preferred and particularly preferred meanings defined above.

From These four embodiments are according to the invention Compounds particularly preferred in which V, W and Y are the meaning Having nitrogen (compounds of general formula (Ia), (Ib), (Id)).

Particular preference is given to those compounds of the formula (I) in which V and Y are the same have nitrogen (compounds of the general formula (Ia), (Id))

Especially most preferred are those compounds of formula (I) in which V is nitrogen (compounds of the general Formula (Ia),

In the compounds of the general formula (I), the substituents and radicals R ¹ to R ⁸ , Q and A have the above general, preferred, particularly preferred, especially preferred and in particular very preferred meanings.

The present invention preferably also the lithium, sodium, potassium, magnesium, calcium, ammonium, C ₁ -C ₄ alkyl ammonium, di (C ₁ -C ₄ alkyl) ammonium , Tri (C ₁ -C ₄ alkyl) ammonium, tetra (C ₁ -C ₄ alkyl) ammonium, tri (C ₁ -C ₄ alkyl) sulfonium, C ₅ - or C ₆ -cycloalkyl-ammonium, di- (C ₁ -C ₂ -alkyl) -benzyl-ammonium and tri- (C ₁ -C ₂ -alkyl) -benzyl-ammonium salts of compounds of the formula (I) in which R ¹ to R ⁸ , A and Q have the above general, preferred, particularly preferred and particularly preferred meanings and which can be prepared by generally customary methods.

The compounds of the general formula (I) can furthermore, if appropriate, be prepared by addition of a suitable inorganic or organic acid, such as, for example, HCl, HBr, H ₂ SO ₄ or HNO ₃ , but also oxalic acid or sulfonic acids to a basic group, such as. As amino or alkylamino, salts. Suitable substituents which are in deprotonated form, such as. For example, sulfonic acids or carboxylic acids, internal salts may in turn form protonatable groups, such as amino groups. Salts may also be formed by reacting with suitable substituents, such as. As sulfonic acids or carboxylic acids, the hydrogen is replaced by a cation suitable in the agrochemical field.

These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts with cations of the formula [NRR'R''R '''] ⁺ , where R to R '''are each independently an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.

In of general formula (I) and all other formulas in In the present invention, the radicals alkyl, alkoxy, Haloalkyl, haloalkoxy, alkylamino, alkylthio, haloalkylthio, alkylsulfinyl, Alkylsulfonyl, Haloalkylsulfinyl and Haloalkylsulfonyl, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton in each case straight-chain or branched be. Unless specifically stated, these radicals are the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, or in the case of unsaturated groups with 2 to 6 C-atoms, in particular 2 to 4 C-atoms, preferred. Alkyl radicals, also in the compound meanings such as alkoxy, Haloalkyl, etc., mean z. As methyl, ethyl, propylene such as n- or i-propyl, butyls such as n-, iso- or tert-butyl, pentyls such as n-pentyl, iso-pentyl or neo-pentyl, hexyls such as n-hexyl, i-hexyl, 3-methylpentyl, 2,2-dimethylbutyl or 2,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexy or 1,4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible corresponding to the alkyl radicals unsaturated radicals; where at least one double bond or triple bond, preferably a double bond or triple bond is included. Alkenyl means z. Vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; Alkynyl means z. Ethynyl, propargyl, But-2-yn-1-yl, but-3-yn-1-yl and 1-methyl-but-3-yn-1-yl.

Cycloalkyl groups are z. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. The cycloalkyl groups may be in bi- or tri-cyclic form occur.

If Haloalkyl groups and haloalkyl radicals of haloalkoxy, haloalkylthio, Haloalkenyl, Haloalkinyl u. a. are indicated in these residues the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms or 2 to 6, in particular 1 to 4 C-atoms or preferably 2 to 4 C-atoms, as well as the corresponding unsaturated and / or substituted radicals in the carbon skeleton in each case straight-chain or branched. Examples are difluoromethyl, 2,2,2-trifluoroethyl, Trifluorallyl, 1-chloroprop-1-yl-3-yl. The term "halo" becomes synonymous with "halogen" according to the invention used.

Alkylene groups these radicals are the lower carbon skeletons, z. B. with 1 to 10 carbon atoms, in particular 1 to 6 carbon atoms or preferably 2 to 4 C atoms (unless otherwise defined), and the corresponding unsaturated and / or substituted Radicals in the carbon skeleton, each straight-chain or can be branched. Examples are methylene, ethylene, n- and i-propylene and n-, s-, i-, t-butylene.

hydroxyalkyl these radicals are the lower carbon skeletons, z. B. with 1 to 6 C-atoms, in particular 1 to 4 C-atoms, as well as the corresponding unsaturated and / or substituted Radicals in the carbon skeleton, each straight-chain or can be branched. Examples of these are 1,2-dihydroxyethyl and 3-hydroxypropyl.

Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl, alkenyl and alkynyl by halogen, preferably by fluorine, chlorine or bromine, in particular by fluorine and / or chlorine, partially or fully substituted alkyl, alkenyl or alkynyl, z. Monohaloalkyl (= monohaloalkyl), perhaloalkyl, CF ₃ , CHF ₂ , CH ₂ F, CF ₃ CF ₂ , CH ₂ FCHCl, CCl ₃ , CHCl ₂ , CH ₂ CH ₂ Cl; Haloalkoxy is z. OCF ₃ , OCHF ₂ , OCH ₂ F, CF ₃ CF ₂ O, OCH ₂ CF ₃ and OCH ₂ CH ₂ Cl; the same applies to haloalkenyl and other halogen-substituted radicals.

aryl means a mono-, bi- or polycyclic aromatic system, for example, phenyl or naphthyl, preferably phenyl.

With the definition "substituted by one or more radicals is "unless otherwise defined, one or more of the same or different residues meant.

The exemplified substituents ("first substituent level") may contain, if they contain hydrocarbonaceous fractions, optionally further substituted there ("second level of substitution"), for example by one of the substituents, as for the first substituent level is defined. Corresponding further substituent levels are possible. Preferably, the term "substituted radical" only one or comprises two levels of substitution.

For radicals with C atoms, those having 1 to 6 C atoms, preferably 1 to 4 C atoms, in particular 1 or 2 C atoms, are preferred. Preferably, substituents from the group halogen are preferred, for. Fluoro and chloro, (C ₁ -C ₄ ) -alkyl, preferably methyl or ethyl, (C ₁ -C ₄ ) -haloalkyl, preferably trifluoromethyl, (C ₁ -C ₄ ) -alkoxy, preferably methoxy or ethoxy, ( C ₁ -C ₄ ) -haloalkoxy, nitro and cyano.

If an aryl radical is substituted, it may preferably be phenyl which is one or more times, preferably up to three times, by identical or different radicals from the group consisting of halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) Alkoxy, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy, cyano and nitro, e.g. B. o-, m- and p-tolyl, di-methylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoromethyl and 2-, 3- and 4-trichloromethyl-phenyl, 2, 4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.

The Compounds of the general formula (I) may vary depending on Type and linkage of the substituents as stereoisomers available. The possible defined by their specific spatial form Stereoisomers such as enantiomers, diastereomers, Z and E isomers are all encompassed by the formula (I).

are for example, one or more alkenyl groups present, so can Diastereomers (Z and E isomers) occur. For example one or more asymmetric carbon atoms present, so can Enantiomers and diastereomers occur. Stereoisomers can be from the mixtures obtained in the preparation according to customary Separation methods obtained. Likewise, stereoisomers can by Use of stereoselective reactions using optically active Starting and / or auxiliaries are selectively prepared. The The invention thus also relates to all stereoisomers derived from the general Formula (I), but not with its specific stereoform are given, as well as their mixtures.

Preparation of the invention Compounds of the general formula (I)

Another The present invention relates to processes for the preparation corresponding compounds of general formula (I) and / or their salts.

mit einem heterocyclischen (Thio)-Carbamat der allgemeinen Formel (III)

umsetzt, worin R¹² ein substituierter oder unsubstituierter (C₁-C₂₀)-Kohlenwasserstoffrest wie Aryl oder Alkyl, vorzugsweise gegebenenfalls substituiertes Phenyl oder gegebenenfalls substituiertes (C₁-C₄)-Alkyl bedeutet und worin V, W, X, Y, R¹ bis R⁸, Q und A die vorstehende Bedeutung aufweisen.In a first embodiment of the present invention, the compounds of the general formula (I) are prepared by reacting (4,5-dihydroisoxazol-3-yl) pyridine-sulfonamides of the general formula (II)

with a heterocyclic (thio) carbamate of the general formula (III)

in which R ^{12 is} a substituted or unsubstituted (C ₁ -C ₂₀ ) -hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (C ₁ -C ₄ ) -alkyl and in which V, W, X, Y, R ¹ to R ⁸ , Q and A have the above significance.

The compounds of general formula (II) can be obtained by reacting the compounds of general formula (X) with a chlorinating agent such as chlorine gas and ammonia solution according to the following reaction scheme:

The compounds of the general formula (X) can in turn be obtained by reacting compounds of the general formula (XI) with benzylmercaptan according to the following reaction scheme starting from the compounds of the general formula (XI):

The compounds of the general formula (XI) can in turn be obtained by ring closure and construction of the heterocycle starting from compounds of the general formula (XII) according to the following reaction scheme:

2-chloronicotinaldehyde oxime and substituted 2-chloronicotinaldehyde oximes are known, for example, from the prior art and can be prepared by methods known to the person skilled in the art (cf. WO 2003/090539 , Helvetica Chimica Acta 59, 211-21 (1976), EP 0 012 158 ).

mit einem Aminoheterocyclus der allgemeinen Formel (V)

umsetzt, worin V, W, X, Y, R¹ bis R⁸, Q und A die vorstehende Bedeutung aufweisen.In a second embodiment of the present invention, the compounds of the general formula (I) are prepared by reacting (4,5-dihydroisoxazol-3-yl) pyridine-sulfonic acid iso (thio) cyanates of the general formula (IV)

with an aminoheterocycle of the general formula (V)

wherein V, W, X, Y, R ¹ to R ⁸ , Q and A are as defined above.

worin R¹² ein substituierter oder unsubstituierter (C₁-C₂₀)-Kohlenwasserstoffrest wie Aryl oder Alkyl, vorzugsweise gebenenfalls substituiertes Phenyl oder gegebenenfalls substituiertes (C₁-C₄)-Alkyl bedeutet, mit einem Aminoheterocyclus der allgemeinen Formel (V)

umsetzt, worin V, W, X, Y, R¹ bis R⁸, Q und A die vorstehende Bedeutung aufweisen.In a third embodiment of the present invention, the compounds of general formula (I) are prepared by reacting sulfonyl (thio) carbamates of general formula (VI)

in which R ¹² denotes a substituted or unsubstituted (C ₁ -C ₂₀ ) -hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (C ₁ -C ₄ ) -alkyl, with an aminoheterocycle of the general formula (V)

wherein V, W, X, Y, R ¹ to R ⁸ , Q and A are as defined above.

mit einem Iso(thio)cyanat der allgemeinen Formel (VII)

gegebenenfalls in Gegenwart eines Reaktionshilfsmittels umsetzt, worin R¹ Wasserstoff bedeutet und R² bis R⁸, V, W, X, Y, Q und A die vorstehende Bedeutung aufweisen.In a fourth embodiment of the present invention, the compounds of general formula (I) are prepared by reacting (4,5-dihydroisoxazol-3-yl) pyridine-sulfonamides of general formula (II)

with an iso (thio) cyanate of the general formula (VII)

optionally in the presence of a reaction auxiliary, wherein R ^{1 is} hydrogen and R ² to R ⁸ , V, W, X, Y, Q and A have the above significance.

zunächst basenkatalysiert mit einem Kohlensäureester, z. B. Diphenylcarbonat, umsetzt und das gebildete Intermediat der allgemeinen Formel (III)

in einer Eintopfreaktion mit einem (4,5-Dihydroisoxazol-3-yl)pyridin-sulfonamid der allgemeinen Formel (II)

umsetzt (vgl. JP1989221366 ), worin V, W, X, Y, R¹ bis R⁸, Q und A die vorstehende Bedeutung aufweisen.In a fifth embodiment of the present invention, the compounds of general formula (I) are prepared by reacting an aminoheterocycle of general formula (V)

initially base catalysed with a carbonic acid ester, eg. B. diphenyl carbonate, and the intermediate formed of the general formula (III)

in a one-pot reaction with a (4,5-dihydroisoxazol-3-yl) pyridine-sulfonamide of the general formula (II)

implements (cf. JP1989221366 ), wherein V, W, X, Y, R ¹ to R ⁸ , Q and A have the above significance.

wobei Hal ein Halogenatom, vorzugsweise Chlor ist, mit einem (Thio)-Cyanat, beispielsweise einem Metall(thio)-cyanat, insbesondere einem Alkalimetall(thio)-cyanat, wie Natrium(thio)cyanat, zu einem Iso(thio)cyanat der Formel (IV)

oder einem solvatisierten (stabilisierten) Derivat davon umsetzt, und anschließend mit einem Aminoheterocyclus der allgemeinen Formel (V)

umsetzt, worin V, W, X, Y, R¹ bis R⁸, Q und A die vorstehende Bedeutung aufweisen.In a sixth embodiment of the present invention, the compounds of the general formula (I) are prepared by reacting (4,5-dihydroisoxazol-3-yl) pyridine-sulphonic acid halides of the general formula (VIII)

wherein Hal is a halogen atom, preferably chlorine, with a (thio) cyanate, for example a metal (thio) cyanate, especially an alkali metal (thio) cyanate, such as sodium (thio) cyanate, to form an iso (thio) cyanate Formula (IV)

or a solvated (stabilized) derivative thereof, and then with an amino heterocycle of the general formula (V)

wherein V, W, X, Y, R ¹ to R ⁸ , Q and A are as defined above.

mit einem heterocyclischen Bis-carbamat der allgemeinen Formel (IX),

worin R¹² ein substituierter oder unsubstituierter (C₁-C₂₀)-Kohlenwasserstoffrest wie Aryl oder Alkyl, vorzugsweise gegebenenfalls substituiertes Phenyl oder gegebenenfalls substituiertes (C₁-C₄)-Alkyl bedeutet, in Gegenwart eines basischen Reaktionshilfsmittels umsetzt, worin V, W, X, Y, R¹ bis R⁸ und A die vorstehende Bedeutung aufweisen.In a seventh embodiment of the present invention, the compounds of general formula (I) with Q = oxygen are prepared by reacting (4,5-dihydroisoxazol-3-yl) pyridine-sulfonic acid amides of general formula (II)

with a heterocyclic bis-carbamate of the general formula (IX),

wherein R ^{12 represents} a substituted or unsubstituted (C ₁ -C ₂₀ ) -hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (C ₁ -C ₄ ) -alkyl, in the presence of a basic reaction auxiliary, wherein V, W , X, Y, R ¹ to R ⁸ and A have the above significance.

zunächst basenkatalysiert mit einem Kohlensäureester, z. B. Diphenylcarbonat, umsetzt und das gebildete Intermediat der allgemeinen Formel (VI)

in einer Eintopfreaktion mit einem Aminoheterocyclus der allgemeinen Formel (V)

umsetzt, worin V, W, X, Y, R¹ bis R⁸, Q und A die vorstehende Bedeutung aufweisen.In an eighth embodiment of the present invention, the compounds of the general formula (I) are prepared by reacting (4,5-dihydroisoxazol-3-yl) pyridine-sulfonic acid amides of the general formula (II)

initially base catalysed with a carbonic acid ester, eg. B. diphenyl carbonate, and the intermediate formed of the general formula (VI)

in a one-pot reaction with an aminoheterocycle of the general formula (V)

wherein V, W, X, Y, R ¹ to R ⁸ , Q and A are as defined above.

All These methods lead to the invention Compounds of the general formula (I).

In the above-mentioned process variants are respectively inert solvents used. Under inert solvents are understood in the context of the present invention as solvents, which are inert under the respective reaction conditions, d. H. especially not react with the starting materials, but not below must be inert to any reaction conditions.

Examples organic solvent, which in the context of the present Can be used in the invention are aromatic or aliphatic solvents, such as benzene, toluene, xylene, mesitylene, Hexane, heptane, octane, cyclohexane; aliphatic and aromatic halogenated hydrocarbons, such as methylene chloride, dichloroethane, chloroform, carbon tetrachloride, Chlorobenzene, dichlorobenzene, ethers, such as diethyl ether, dibutyl ether, Diisobutyl ether, methyl tert-butyl ether, isopropyl ethyl ether, diisopropyl ether, Tetrahydrofuran, and dioxane; also dimethyl sulfoxide, and acid amide derivatives, such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone, as well as carboxylic esters, such as ethyl acetate, or else also diglyme, dimethyl glycol; Nitriles such as acetonitrile, propionitrile or butyronitrile and ketones such as acetone, methyl ethyl ketone or Cyclohexanone. Particularly preferred are toluene, xylene, dichlorobenzene, Chlorobenzene, acetonitrile, acetone, butyronitrile or ethyl acetate. However, the present invention is not illustrative of the above limited solvents mentioned.

The Reaction temperature at which the reactions according to the above embodiments are performed can vary widely. For example the reactions can be carried out at a temperature of 0 to 100 ° C, preferably 20 to 70 ° C, are performed.

Of the Reactions of the present invention are generally described below Normal pressure performed. However, it is also possible under increased pressure or reduced pressure - in Generally between 0.1 bar and 10 bar - to work.

The Process for the preparation of the inventive N-azinyl-N'-pyridylsulfonylureas of the general formula (I) are optionally in the presence of a basic reaction auxiliary carried out.

As such, all customary inorganic or organic bases are suitable. These include, for example, alkali metal or alkaline earth metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as lithium, sodium, potassium or calcium hydride, lithium, sodium or potassium amide, sodium or Potassium methoxide, sodium or potassium ethylate, sodium or potassium propylate, aluminum isopropylate, sodium or potassium tert-butoxide, sodium or potassium hydroxide, ammonium hydroxide, sodium, potassium or calcium acetate, ammonium acetate, sodium, potassium or calcium carbonate, ammonium carbonate , Sodium or potassium bicarbonate, and basic organic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethylcyclo hexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, 2-methyl, 3-methyl and 4-methylpyridine, 2,4-dimethyl, 2,6-dimethyl, 3, 4-dimethyl- and 3,5-dimethylpyridine, 5-ethyl-2-methylpyridine, N-methylpyridine, 4- (N, N-dimethylamino) -pyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU ).

Intermediate

Another The present invention also provides certain intermediates, which according to the synthetic routes shown above in the preparation of the compounds of the invention of the general formula (I).

in welchen die Reste V, W, X, Y, R⁴, R⁵, R⁶, R⁷ und R⁸ die bereits weiter oben angegebenen allgemeinen, bevorzugten und besonders bevorzugten Bedeutungen aufweisen.Accordingly, in a first embodiment of the intermediates, the present invention also relates to compounds of the general formula (II)

in which the radicals V, W, X, Y, R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 have} the general, preferred and particularly preferred meanings given above.

in welchen die Reste V, W, X, Y, R⁴, R⁵, R⁶, R⁷, R⁸ und Q die bereits weiter oben angegebenen allgemeinen, bevorzugten und besonders bevorzugten Bedeutungen aufweisen.Another object of the present invention are in a second embodiment of the intermediates and compounds of general formula (IV)

in which the radicals V, W, X, Y, R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and Q have the general, preferred and particularly preferred meanings given above.

in welchen die Reste V, W, X, Y, R⁴, R⁵, R⁶, R⁷ und R⁸ die bereits weiter oben angegebenen allgemeinen, bevorzugten und besonders bevorzugten Bedeutungen aufweisen.A further subject of the present invention in a third embodiment of the intermediates are also compounds of the general formula (X)

in which the radicals V, W, X, Y, R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 have} the general, preferred and particularly preferred meanings given above.

in welchen die Reste V, W, X, Y, R⁴, R⁵, R⁶, R⁷, R⁸ und Hal die bereits weiter oben angegebenen allgemeinen, bevorzugten und besonders bevorzugten Bedeutungen aufweisen.Another object of the present invention are in a fourth embodiment of the intermediates and compounds of general formula (XI)

in which the radicals V, W, X, Y, R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and Hal have the general, preferred and particularly preferred meanings given above.

in welchen die Reste V, W, X, Y, R⁴, R⁵, R⁶, R⁷, R⁸ und Hal die bereits weiter oben angegebenen allgemeinen, bevorzugten und besonders bevorzugten Bedeutungen aufweisen.A further subject matter of the present invention, in a fifth embodiment of the intermediates, is also compounds of the general formula (VIII)

in which the radicals V, W, X, Y, R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and Hal have the general, preferred and particularly preferred meanings given above.

in welchen die Reste V, W, X, Y, R⁴, R⁵, R⁶, R⁷, R⁸ R¹² und Q die bereits weiter oben angegebenen allgemeinen, bevorzugten und besonders bevorzugten Bedeutungen aufweisen.A further subject matter of the present invention, in a sixth embodiment of the intermediates, is also compounds of the general formula (VI)

in which the radicals V, W, X, Y, R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ R ¹² and Q have the general, preferred and particularly preferred meanings given above.

Libraries of compounds of formula (I) and / or their salts, which can be synthesized after the above reactions, can also be prepared in a parallelized manner, which can be done in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is understood as a procedure, as for example by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34 is described.

to parallelized reaction procedure and workup can use a number of commercially available devices used, for example, calypso reaction blocks (Caylpso reaction blocks) from Barnstead International, Dubuque, Iowa 52004-0797, USA or reaction stations Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Massachusetts 02451, USA. For the parallelized Purification of compounds of general formula (I) and their Salts or of intermediate products produced during production Among other things, chromatographic equipment is available, for example, the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

The listed equipment lead to a modular Procedure in which the individual work steps are automated However, between the steps, manual operations must be performed. This can be done by the Use of partially or fully integrated automation systems bypassed where the respective automation modules for example be operated by robots. Such automation systems can for example, from Caliper, Hopkinton, MA 01748, USA become.

The Carrying out single or multiple synthesis steps through the use of polymer-supported reagents / scavanger resins get supported. In the literature are a number described by experimental protocols, for example in ChemFiles, Vol. 4, no. 1, Polymer-Supported Scavengers and Reagents for Solution Phase Synthesis (Sigma-Aldrich).

In addition to the methods described herein, the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods. For this purpose, individual intermediates or all intermediates of the synthesis or adapted for the appropriate approach synthesis are bound to a synthetic resin. Solid-phase assisted synthesis methods are well described in the literature, eg. B. Barry A. Bunin in The Combinatorial Index, Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley, 1999 , The use of solid-phase assisted synthetic methods allows a number of protocols known from the literature, which in turn can be carried out manually or automatically. For example, the "teabag method" (Houghten, US 4,631,211 ; Houghten et al., Proc. Natl. Acad. Sci., 1985, 82, 5131-5135 ) with products from IRORI, 11149 North Torreg Pines Road, La Jolla, CA 92037, USA. The automation of solid-phase assisted parallel synthesis succeeds, for example, by equipment of the companies Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany. The reactions can also be carried out, for example, by means of IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.

Both solid and liquid phases can be supported by the implementation of single or multiple synthetic steps through the use of microwave technology. In the literature, a number of experimental protocols are described, for example in Microwaves in Organic and Medicinal Chemistry (published by CO Kappe and A. Stadler), published by Wiley, 2005 ,

The Preparation according to the methods described here provides compounds of formula (I) and their salts in the form of Substance collections called libraries. object The present invention also provides libraries which are at least two compounds of formula (I) and their salts.

Another The invention is due to the herbicidal property the compounds of the general formula (I) also the use the compounds of the invention of the general Formula (I) as herbicides for controlling harmful plants.

Another The invention is due to the herbicidal property the compounds of the general formula (I) also the use the compounds of the invention of the general Formula (I) as herbicides for controlling harmful plants.

With external conditions such as temperature, humidity, the type of herbicide used, varies u. a. the required Application rate of the compounds of the formula (I). She can be inside continue to fluctuate borders, z. B. between 0.001 and 10,000 g / ha or more active substance, but preferably it is between 0.5 and 5000 g / ha, preferably between 0.5 and 1000 g / ha and especially preferably between 0.5 and 500 g / ha.

The Compounds of the formula (I) according to the invention and their salts, hereinafter synonymously also as compounds of the formula (I) have an excellent herbicidal Efficiency against a broad spectrum economically more important monocotyledonous and dicotyledonous harmful plants. Also difficult to combat Perennial weeds made from rhizomes, rootstalks or other permanent organs are eliminated by the active ingredients well recorded. It does not matter if the Substances applied in the pre-sowing, pre-emergence or post-emergence process become.

In the individual examples may be mentioned some representatives of the monocotyledonous and dicotyledonous weed flora, the can be controlled by the compounds of the general formula (I) according to the invention, without being limited by naming a restriction to certain types.

On the side of the monocotyledonous weed species are z. B. Agrostis, Alopecurus, Apera, Avena, Brachicaria, Bromus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Festuca, Fimbristylis, Ischaemum, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Sagittaria, Scirpus, Setaria, Sphenoclea, as well as Cyperusarten predominantly the annuell group and the perennial species Agropyron, Cynodon, Imperata and Sorghum, as well as perennial Cyperus species well recorded.

at dicotyledonous weed species extends the spectrum of action on species such as B. Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida on the annuelle Page as well as Convolvulus, Cirsium, Rumex and Artemisia at the perennial Weeds. In addition, herbicidal activity is added dicotyledonous weeds such as Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rotala, Seneceio, Sesbania, Solanum, Sonchus, Taraxacum, Trifolium, Urtica and Xanthium observed.

Become the compounds of the invention of the general Formula (I) applied to the surface of the earth before germination, so either the emergence of the weed seedlings is complete prevents or the weeds grow up to the cotyledon stage But then they stop growing and eventually die completely after three to four weeks.

at Application of the active compounds of the general formula (I) to the green Plant parts postemergence also occurs very quickly after the treatment a drastic halt in growth and the weed plants stay in the growth stage at the time of application stand or die completely after a certain time, so that on this way harmful to crops Weed competition is eliminated very early and sustainably.

Although the compounds of the invention of the general Formula (I) has excellent herbicidal activity monocotyledonous and dicotyledonous weeds, become crop plants economically important crops such. Wheat, barley, rye, Rice, maize, sugar beet, cotton, rapeseed and soy only marginally or not damaged at all. The present compounds For these reasons, they are very well suited for selective use Control of undesirable plant growth in agricultural crops.

About that In addition, the substances according to the invention the general formula (I) excellent growth regulatory Properties on crops. They regulate in the plant 's own metabolism and can thus targeted influencing of phytonutrients and harvest relief such as B. by triggering desiccation and stunted growth be used. Furthermore, they are also suitable for general Control and inhibition of unwanted vegetative growth, without killing the plants. An inhibition of the vegetative Growth plays a big role in many mono- and dicotyledonous cultures Role, since the storage thereby reduced or completely prevented can be.

by virtue of their herbicidal and plant growth regulatory properties The active ingredients can also be used to combat Harmful plants in cultures of known or yet to be developed genetically modified plants are used. The Transgenic plants are usually characterized by particular beneficial Properties, for example, by resistance to certain pesticides, especially certain herbicides, resistance against plant diseases or pathogens of plant diseases like certain insects or microorganisms like fungi, bacteria or viruses. Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, Composition and special ingredients. So are transgenic Plants with increased starch content or altered quality the starch or those with other fatty acid composition the crop is known. Other special features can be in a tolerance or resistance to abiotic stressors z. As heat, cold, drought, salt and ultraviolet radiation lie.

Prefers is the application of the compounds of the invention of the general formula (I) or salts thereof in economically significant transgenic crops of useful and ornamental plants, e.g. B. of cereals such as Wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soy, rapeseed, potato, Tomato, pea and other vegetables.

Preferably, the compounds of general formula (I) as herbicides in Nutzpflanzenenkul used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.

conventional Ways of producing new plants compared to previously existing plants have modified properties exist for example, in classical breeding methods and the Generation of mutants.

• – gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/011376 , WO 92/014827 , WO 91/019806 ),
• – transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ Glufosinate (vgl. z. B. EP 0242236 , EP 0242246 ) oder Glyphosate ( WO 92/000377 ) oder der Sulfonylharnstoffe ( EP 0257993 , US 5013659 ) resistent sind,
• – transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit Bacillus thuringiensis-Toxine (Bt-Toxine) zu produzieren, welche die Pflanzen gegen bestimmte Schädlinge resistent machen ( EP 0142924 , EP 0193259 ).
• – transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung ( WO 91/013972 ).
• – gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder Sekundärstoffen z. B. neuen Phytoalexinen, die eine erhöhte Krankheitsresistenz verursachen ( EP 0309862 , EP 0464461 )
• – gentechnisch veränderte Pflanzen mit reduzierter Photorespiration, die höhere Erträge und höhere Stresstoleranz aufweisen ( EP 0305398 )
• – transgene Kulturpflanzen, die pharmazeutisch oder diagnostisch wichtige Proteine produzieren („molecular pharming")
• – transgene Kulturpflanzen, die sich durch höhere Erträge oder bessere Qualitat auszeichnen
• – transgene Kulturpflanzen die sich durch eine Kombinationen z. B. der o. g. neuen Eigenschaften auszeichnen („gene stacking")

Alternatively, new plants with altered properties can be generated by means of genetic engineering methods (see, for example, US Pat. EP 0221044 . EP 0131624 ). For example, several cases have been described

• - genetic modification of crops to modify the starch synthesized in the plants (eg. WO 92/011376 . WO 92/014827 . WO 91/019806 )
• Transgenic crops which are resistant to certain glufosinate-type herbicides (cf. EP 0242236 . EP 0242246 ) or glyphosate ( WO 92/000377 ) or the sulfonylureas ( EP 0257993 . US 5013659 ) are resistant,
• Transgenic crops, such as cotton, capable of producing Bacillus thuringiensis toxins (Bt toxins) which render plants resistant to certain pests ( EP 0142924 . EP 0193259 ).
• Transgenic crops with modified fatty acid composition ( WO 91/013972 ).
• - Genetically modified crops with new content or secondary substances z. B. new phytoalexins causing increased disease resistance ( EP 0309862 . EP 0464461 )
• - genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance ( EP 0305398 )
• Transgenic crops producing pharmaceutically or diagnostically important proteins ("molecular pharming")
• - Transgenic crops characterized by higher yields or better quality
• - Transgenic crop plants which are characterized by a combination of z. B. the above-mentioned new properties ("gene stacking")

Numerous molecular biological techniques that can be used to produce new transgenic plants with altered properties are known in principle; see, for. B. I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, "Trends in Plant Science" 1 (1996) 423-431) ,

For such genetic engineering, nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see, for example, US Pat. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY ; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996

The Production of plant cells with reduced activity For example, a gene product can be obtained by expression at least one corresponding antisense RNA, a sense RNA for Obtaining a Cosuppressionseffektes or expression at least a suitably engineered ribozyme that specifically transcripts of the above gene product cleaves.

For this On the one hand, DNA molecules can be used including the entire coding sequence of a gene product possibly existing flanking sequences, as well DNA molecules that comprise only parts of the coding sequence, These parts need to be long enough to be in the cells to cause an antisense effect. It is also possible Use of DNA sequences that have a high degree of homology but not to the coding sequences of a gene product are completely identical.

In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to the person skilled in the art (see, for example Braun et al., EMBO J. 11 (1992), 3219-3227 ; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850 ; Sonnewald et al., Plant J. 1 (1991), 95-106) , The expression of the nucleic acid molecules can also take place in the organelles of the plant cells.

The Transgenic plant cells can be prepared by known techniques be regenerated to whole plants. In the transgenic plants they can in principle be plants of any plant species, d. h., both monocotyledonous and dicotyledonous plants.

So Transgenic plants are available that changed Characteristics by overexpression, suppression or inhibition homologous (= natural) genes or gene sequences or expression heterologous (= foreign) genes or gene sequences.

Preferably can the compounds of the invention of general formula (I) are used in transgenic cultures, which against growth substances, such. Dicamba or herbicides, the essential plant enzymes, eg. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate Dioxygenases (HPPD) inhibit, respectively against herbicides from the group sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous drugs, are resistant.

at the application of the active compounds according to the invention of the general formula (I) in transgenic cultures occur in addition to the in other cultures to be observed Harmful plants often have effects on the application are specific in the respective transgenic culture, for example a modified or specially extended weed spectrum, which can be combated, changed application rates, that can be used for the application preferably good combinability with the herbicides, compared which the transgenic culture is resistant, as well as influencing Growth and yield of transgenic crops.

object Therefore, the invention is also the use of the invention Compounds of the general formula (I) as herbicides for controlling of harmful plants in transgenic crops.

The Compounds of the general formula (I) can be different Art formulated, depending on which biological and / or chemical-physical Parameters are specified. As formulation options are for example in question: wettable powder (WP), water-soluble Powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil or water based dispersions, oil miscible Solutions, capsule suspensions (CS), dusts (DP), mordant, granules for litter and soil application, Granules (GR) in the form of micro, spray, elevator and Adsorption granules, water-dispersible granules (WG), water-soluble Granules (SG), ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and are described, for example, in: Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986 . Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973 ; K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London ,

The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and other additives are likewise known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers" . 2nd Ed., Darland Books, Caldwell NJ, H.v. Olphen, "Introduction to Clay Colloid Chemistry" ; 2nd Ed., J. Wiley & Sons, NY ; C. Marsden, "Solvents Guide" ; 2nd Ed., Interscience, NY 1963 ; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964 ; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Publishing company, Stuttgart 1976 ; Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986 , On the basis of these formulations, combinations with other pesticide-active substances such. As insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and / or growth regulators produce, for. B. in the form of a finished formulation or as a tank mix.

wettable powder are preparations which are evenly dispersible in water, besides the active substance except a dilution or inert or surfactants of ionic and / or nonionic nature (Wetting agent, dispersant), z. For example, polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, Alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid Sodium or oleoylmethyltaurine sodium. to Production of the wettable powders, the herbicidal active ingredients, for example in conventional apparatus such as hammer mills, blower mills and air-jet mills finely ground and at the same time or then mixed with the formulation auxiliaries.

emulsifiable Concentrates are made by dissolving the active ingredient in one organic solvents z. Butanol, cyclohexanone, dimethylformamide, Xylene or higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with addition of one or more ionic and / or nonionic surfactants Art (emulsifiers) produced. As emulsifiers, for example alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, Alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, Alkyl polyether, sorbitan esters such. B. sorbitan fatty acid esters or Polyoxethylenensorbitanester such. B. Polyoxyethylensorbitanfettsäureester.

dusts obtained by grinding the active ingredient with finely divided solid substances, eg. Talc, natural clays such as kaolin, Bentonite and pyrophyllite, or diatomaceous earth.

suspension concentrates can be water or oil based. You can for example, by wet grinding by means of commercial Bead mills and optional addition of surfactants, such as they z. B. already listed above for the other formulation types are to be produced.

emulsions z. As oil-in-water emulsions (EW), can be, for example by means of stirring, colloid mills and / or static Mixers using aqueous organic Solvents and, where appropriate, surfactants, as z. B. already listed above for the other formulation types are, manufacture.

granules can either by spraying the active ingredient made on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, z. As polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, Kaolinite or granulated inert material. Also can suitable active ingredients in the usual for the production of fertilizer granules Were - if desired, mixed with fertilizers - granulated.

Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material. For the preparation of plate, fluidized bed, extruder and spray granules see, for. B. Method in "Spray-Drying Handbook" 3rd Ed. 1979, G. Goodwin Ltd., London ; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff ; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57 ,

For more details on pesticide formulation see, e.g. B. GC Klingman, "Weed Control as a Science," John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103 ,

The agrochemical preparations usually contain from 0.1 to 99% by weight, in particular 0.1 to 95 wt .-%, active ingredient of the formula (I).

In Spray powders is the active ingredient concentration z. B. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional Formulation components. For emulsifiable concentrates can the drug concentration is about 1 to 90, preferably 5 to 80 Wt .-% amount. Contain dusty formulations 1 to 30% by weight of active compound, preferably in most cases 5 to 20% by weight on active ingredient, sprayable solutions about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient. In the case of water-dispersible Granules, the active substance content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers u. a. used become. For the water-dispersible granules, the content is of active ingredient, for example, between 1 and 95 wt .-%, preferably between 10 and 80% by weight.

Besides If necessary, the active substance formulations mentioned contain the customary adhesion, wetting, dispersing, emulsifying, Penetration, preservative, antifreeze and solvents, Fillers, carriers and dyes, defoamers, Evaporation inhibitor and the pH and the viscosity affecting Medium.

The compounds of the general formula (I) or salts thereof can be used as such or in the form of their formulations (formulations) with other pesticide-active substances, such as. As insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators can be used in combination, eg. B. as a ready-made formulation or as tank mixes. As a combination partner for the active compounds of the general formula (I) according to the invention in mixed formulations or in the tank mix, for example, known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-Co enzyme A-carboxylase, PS I, PS II, HPPDO, phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, 5-enolpyrvvylshikimate-3-phosphate synthetase or cellulose biosynthesis are used. Such compounds and other useful compounds with partially unknown or other mechanism of action are, for. In Weed Research 26, 441-445 (1986) , or "The Pesticide Manual", 11th edition 1997 (hereinafter also abbreviated to "PM") and 12th edition 2000, The British Crop Protection Council and the Royal Soc. of Chemistry (Editor) , and literature cited therein. As literature-known herbicides, which can be combined with the compounds of formula (I), z. The following compounds are to be mentioned (note: the compounds are denoted either by the "common name" according to the International Organization for Standardization (ISO) or by the chemical name, if appropriate together with a customary code number):
acetochlor; acifluorfen (-sodium); aclonifen; AKH 7088, ie methyl [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidene] amino] oxy] acetic acid and acetic acid; acrolein; alachlor; alloxydim (-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid, amitrole; AMS, ie ammonium sulfamate; anilofos; asulam; atraton; atrazine; azafenidin, azimsulfuron (DPX-A8947); aziprotryn; barban; BAS 516H, ie 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; BCPC; beflubutamide, benazoline (-ethyl); benfluralin; benfuresate; bensulfuron (-methyl); bensulide; bentazone; benzfendizone; benzobicyclone, benzofenap; benzofluor; benzoylprop (-ethyl); benzthiazuron; bifenox; bialaphos; bifenox; bispyribac (-sodium), borax; bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil, butamifos; butenachlor; buthidazole; butraline; butroxydim, butylate; cacodylic acid; calcium chlorates; cafenstrole (CH-900); carbetamide; carfentrazone (-ethyl); caloxydim, CDAA, ie 2-chloro-N, N-di-2-propenylacetamide; CDEC, ie diethyldithiocarbamic acid 2-chloroallyl ester; chlorflurenol (-methyl); chlomethoxyfen; clethodim; clomeprop; chloramben; chlorazifop-butyl, chloromesulon; chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron (-ethyl); chloroacetic acid; chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal (dimethyl); chlorthiamid; chlorotoluron, cinidone (-methyl and -ethyl), cinmethylin; cinosulfuron; cisanilide; clefoxydim, clethodim; clodinafop and its ester derivatives (eg clodinafop-propargyl); clomazone; clomeprop; cloproxydim; clopyralid; clopyrasulfuron (-methyl); cloransulam (-methyl), cresol; cumyluron (JC 940); cyanamide; cyanazine; cycloate; Cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (eg, butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-D, 2,4-DB, 3,4-DA, 3,4-DB, 2,4-DEB, dalapone; dazomed; desmedipham; Desmetryn; di-allate; dicamba; dichlobenil; ortho-dichlorobenzene; para-dichlorobenzene; dichloroprop; dichlorprop-P; diclofop and its esters such as diclofop-methyl; diclosulam, diethatyl (-ethyl); difenoxuron; difenzoquat; difenzoquat methylsulphate; diflufenican; diflufenzopyr, dimefuron; dimepiperate, dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethenamid-P; dimethazone, dimexyflam, dimethipine; di-methylarsinic acid; dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat; diquat-dibromide; dithiopyr; diuron; DNOC; 3,4-DP; DSMA; EBEP; eglinazine-ethyl; EL77, ie 5-cyano-1- (1,1-dimethylethyl) -N-methyl-1H-pyrazole-4-carboxamide; endothal; epoprodan, EPTC; esprocarb; ethalfluralin; ethametsulfuron (-methyl); Ethidimuron; ethiozin; ethofumesate; ethoxyfen and its esters (eg ethyl ester, HN-252); ethoxysulfuron, etobenzanide (HW 52); F5231, ie N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide; fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters, eg. Fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim; fentrazamide, fenuron; -ferrous sulphate; flamprop (-methyl or -isopropyl or -isopropyl-L); flazasulfuron; floazulate, florasulam, fluazifop and fluazifop-P and their esters, e.g. Fluazifop-butyl and fluazifop-p-butyl; fluazolate; flucarbazone (-sodium), flucetosulfuron; fluchloralin; flufenacet; flufenpyr (-ethyl); flumetsulam; flumeturon; flumiclorac (pentyl), flumioxazine (S-482); flumipropyn; fluometuron, fluorochloridone, fluorodifen; fluoroglycofen (-ethyl); flupoxam (KNW-739); flupropacil (UBIC-4243); flupropanate, flupyrsulfuron (-methyl or -sodium), flurenol (-butyl), fluridone; flurochloridone; fluroxypyr (-meptyl); flurprimidol; flurtamone; fluthiacet (-methyl) (KIH-9201); fluthiamide; fomesafen; foramsulfuron; fosamine; furyloxyfen; glufosinate (-ammonium); glyphosate (-isopropylammonium); halo safen; halosulfuron (-methyl) and its esters (eg, methyl ester, NC-319); haloxyfop and its esters; haloxyfop-P (= R-haloxyfop) and its esters; HC-252; hexazinone; imazamethabenz (-methyl); imazapyr; imazaquin and salts such as the ammonium salt; imazamethapyr, imazamox, imazapic, imazethamethapyr; imazethapyr; imazosulfuron; indanofan, iodomethane; iodosulfuron (methylsodium); ioxynil; isocarbamid; isopropalin; isoproturon; isouron; isoxaben; isoxachlortole, isoxaflutole, isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MAA; MUMMY; MCPA; MCPA-2-ethylhexyl; MCPA-thioethyl; MCPB; mecoprop; mecoprop-P; mefenacet; mefluidide; mesosulfuron (-methyl); mesotrione, metamifop; metamitron; metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone; methylarsonic acid; methyldymron; methyl isothiocyanate; metabenzuron, metamifop; methobenzuron; metobromuron; (Alpha-) metolachlor; S-metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MK-616; MH; molinate; monalide; monocarbamide dihydrogen sulfates; monolinuron; monuron; monosulfuron; MSMA; MT 128, ie 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazineamine; MT 5950, ie N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen; nona noic acid; norflurazon; Oleic acid (fatty acid); orbencarb; orthosulfamuron; oryzalin; oxadiargyl (RP-020630); oxadiazon; oxasulfuron, oxaziclomefone, oxyfluorfen; paraquat; paraquat-dichloride; pebulate; pelargonic acid, pendimethalin; penoxsulam; pentachlorophenol; Pentanochlor; pentoxazone, perfluidone; phenisopham; phenmedipham (ethyl); pethoxamid; picloram; picolinafen, pinoxaden, piperophos; piributicarb; pirifenopbutyl; pretilachlor; primisulfuron (-methyl); potassium arsenite; potassium azide; procarbazone- (sodium), procyazine; prodi amines; profluazol; profluralin; profoxydim; proglinazine (-ethyl); prometon; prometryne; propachlor; propanil; propaquizafop and its esters; propazine; propham; propisochlor; propoxycarbazone (-sodium) (BAY MKH 6561); Propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor; pyraclonil; pyraflufen (-ethyl), pyrasulfotole; pyrazolinate; pyrazon; pyrazosulfuron (-ethyl); pyrazoxyfen; pyribambenz-isopropyl; pyribenzoxime, pyributicarb, pyridafol, pyridate; pyriftalid; pyrimidobac (-methyl), pyrimisulfan, pyrithiobac (-sodium) (KIH-2031); pyroxasulfone; pyroxofop and its esters (eg propargyl esters); pyroxsulam (triflosulam); quinclorac; quinmerac; quinoclamine, quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives z. Eg quizalofop-ethyl; quizalofop-P-tefuryl and -ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, ie 2- [4-chloro-2-fluoro-5- (2-propynyloxy) -phenyl] -4,5,6,7-tetrahydro-2H-indazole; saflufenacil (CAS RN: 372137-35-4); secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, ie 2 - [[7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthalenyl] oxy] propanoic acid and methyl ester; SMA; sodium arsenite; sodium azide; sodium chlorates; sulcotrione, sulfentrazone (FMC-97285, F-6285); sulfazuron; sulfometuron (-methyl); sulfosate (ICI-A0224); sulfosulfuron, 2,3,6-TBA; TCA (sodium); tebutam (GCP-5544); tebuthiuron; tefuryltrione, tembotrione, tepraloxydim, terbacil; terbucarb; terbuchlor; terbumeton; Terbuthylazine; terbutryn; TFH 450, ie, N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1H-1,2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiafluamide, thiazafluron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thiencarbazone-methyl, thifensulfuron (-methyl); thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triaziflam, triazofenamide; tribenuron (-methyl); tricamba; triclopyr; tridiphane; trietazine; trifloxysulfuron (sodium); trifluralin; triflusulfuron-methyl and esters (eg, methyl ester, DPX-66037); trihydroxytriazine; trimeturon; tritosulfuron; tropramezone; tsitodef; vernolate; [3- [2-chloro-4-fluoro-5- (1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-3-yl) phenoxy] -2-pyridyloxy] acetic acid ethyl ester; WL 110547, ie 5-phenoxy-1- [3- (trifluoromethyl) -phenyl] -1H-tetrazole; UBH-509; D-489; LS 82-556, ie [(S) -3-N- (methylbenzyl) carbamoyl-5-propionyl-2,6-lutidine]; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; Dowco-535; DK-8910; V-53482; PP-600; MBH-001; ET-751, d. h ethyl [2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-fluoro-phenoxy] -acetate; KIH-6127, ie pyriminobac-methyl; KIH-2023, ie bispyribac sodium; and SYP-249, d. h ethyl 2- {2-nitro-5 - [(2-chloro-4-trifluoromethyl) -phenoxy] -benzoxy} -3-methyl-3-butenoate; SYN 523rd

wobei die Symbole und Indizes folgende Bedeutungen haben:
n_A ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3;
R_A ¹ ist Halogen, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, Nitro oder (C₁-C₄)Haloalkyl;
W_A ist ein unsubstituierter oder substituierter divalenter heterocyclischer Rest aus der Gruppe der teilungesättigten oder aromatischen Fünfring-Heterocyclen mit 1 bis 3 Heteroringatomen aus der Gruppe N und O, wobei mindestens ein N-Atom und höchstens ein O-Atom im Ring enthalten ist, vorzugsweise ein Rest aus der Gruppe (W_A ¹) bis (W_A ⁴),

m_A ist 0 oder 1;
R_A ² ist OR_A ³, SR_A ³ oder NR_A ³R_A ⁴ oder ein gesättigter oder ungesättigter 3- bis 7-gliedriger Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonylgruppe in (S1) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel OR_A ³, NHR_A ⁴ oder N(CH₃)₂, insbesondere der Formel OR_A ³;
R_A ³ ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C-Atomen;
R_A ⁴ ist Wasserstoff, (C₁-C₆)Alkyl, (C₁-C₆)Alkoxy oder substituiertes oder unsubstituiertes Phenyl;
R_A ⁵ ist H, (C₁-C₈)Alkyl, (C₁-C₈)Haloalkyl, (C₁-C₄)Alkoxy(C₁-C₈)Alkyl, Cyano oder COOR_A ⁹, worin R_A ⁹ Wasserstoff, (C₁-C₈)Alkyl, (C₁-C₈)Haloalkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl, (C₁-C₆)Hydroxyalkyl, (C₃-C₁₂)Cycloalkyl oder Tri-(C₁-C₄)-alkyl-silyl ist;
R_A ⁶, R_A ⁷, R_A ⁸ sind gleich oder verschieden Wasserstoff, (C₁-C₈)Alkyl, (C₁-C₈)Haloalkyl, (C₃-C₁₂)Cycloalkyl oder substituiertes oder unsubstituiertes Phenyl;
vorzugsweise:

• a) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (S1^a), vorzugsweise Verbindungen wie 1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäure, 1-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäureethylester (S1-1) ("Mefenpyr-diethyl"), und verwandte Verbindungen, wie sie in der WO-A-91/07874 beschrieben sind;
• b) Derivate der Dichlorphenylpyrazolcarbonsäure (S1^b), vorzugsweise Verbindungen wie 1-(2,4-Dichlorphenyl)-5-methyl-pyrazol-3-carbonsäureethylester (S1-2), 1-(2,4-Dichlorphenyl)-5-isopropyl-pyrazol-3-carbonsäureethylester (S1-3), 1-(2,4-Dichlorphenyl)-5-(1,1-dimethyl-ethyl)pyrazol-3-carbonsäureethyl-ester (S1-4) und verwandte Verbindungen, wie sie in EP-A-333 131 und EP-A-269 806 beschrieben sind;
• c) Derivate der 1,5-Diphenylpyrazol-3-carbonsäure (S1^c), vorzugsweise Verbindungen wie 1-(2,4-Dichlorphenyl)-5-phenylpyrazol-3-carbonsäureethylester (S1-5), 1-(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester (S1-6) und verwandte Verbindungen wie sie beispielsweise in der EP-A-268554 beschrieben sind;
• d) Verbindungen vom Typ der Triazolcarbonsäuren (S1^d), vorzugsweise Verbindungen wie Fenchlorazol(-ethylester), d. h. 1-(2,4-Dichlorphenyl)-5-trichlormethyl-(1H)-1,2,4-triazol-3-carbonsäureethylester (S1-7), und verwandte Verbindungen wie sie in EP-A-174 562 und EP-A-346 620 beschrieben sind;
• e) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3-carbonsäure oder der 5,5-Diphenyl-2-isoxazolin-3-carbonsäure (S1^e), vorzugsweise Verbindungen wie 5-(2,4-Dichlorbenzyl)-2-isoxazolin-3-carbonsäureethylester (S1-8) oder 5-Phenyl-2-isoxazolin-3- carbonsäureethylester (S1-9) und verwandte Verbindungen, wie sie in WO-A-91/08202 beschrieben sind, bzw. 5,5-Diphenyl-2-isoxazolin-carbonsäure (S1-10) oder 5,5-Diphenyl-2-isoxazolin-carbonsäureethylester (S1-11) ("Isoxadifen-ethyl") oder -n-propylester (S1-12) oder der 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3-carbonsäureethylester (S1-13), wie sie in der Patentanmeldung WO-A-95/07897 beschrieben sind.

Of particular interest is the selective control of harmful plants in crops of commercial and ornamental plants. Although the compounds of the general formula (I) according to the invention already have very good to sufficient selectivity in many cultures, phytotoxicities on the crop plants can in principle occur in some crops and, above all, in the case of mixtures with other herbicides which are less selective. In this connection, combinations of compounds of the general formula (I) according to the invention which are of particular interest and which contain the compounds of the general formula (I) or their combinations with other herbicides or pesticides and safeners are of particular interest. The safeners, which are used in an antidote effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, eg. B. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals. The following groups of compounds are suitable, for example, as safeners for the compounds (I), alone or in combinations thereof with other pesticides:
The safeners are preferably selected from the group consisting of:
S1) compounds of the formula (S1),

where the symbols and indices have the following meanings:
n _A is a natural number from 0 to 5, preferably 0 to 3;
R _A ¹ is halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, nitro or (C ₁ -C ₄ ) haloalkyl;
W _A is an unsubstituted or substituted divalent heterocyclic radical from the group of the unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring N and O groups, wherein at least one N atom and at most one O atom is contained in the ring, preferably a radical from the group (W _A ¹ ) to (W _A ⁴ ),

m _A is 0 or 1;
R _A ² is OR _A ³ , SR _A ³ or NR _A ³ R _A ⁴ or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N atom with the carbonyl group in (S1) and unsubstituted or substituted by radicals from the group (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or optionally substituted phenyl, preferably a radical of the formula OR _A ³ , NHR _A ⁴ or N (CH ₃ ) ₂ , in particular of the formula OR _A ³ ;
R _A ³ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
R _A ⁴ is hydrogen, (C ₁ -C ₆ ) alkyl, (C ₁ -C ₆ ) alkoxy or substituted or unsubstituted phenyl;
R _A ⁵ is H, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₁ -C ₄ ) alkoxy (C ₁ -C ₈ ) alkyl, cyano or COOR _A ⁹ , wherein R _A ^{9 is} hydrogen, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkyl, (C ₁ -C ₆ ) hydroxyalkyl, (C ₃ -C ₁₂ ) is cycloalkyl or tri (C ₁ -C ₄ ) alkylsilyl;
R _A ⁶ , R _A ⁷ , R _A ⁸ are identical or different hydrogen, (C ₁ -C ₈ ) alkyl, (C ₁ -C ₈ ) haloalkyl, (C ₃ -C ₁₂ ) cycloalkyl or substituted or unsubstituted phenyl;
preferably:

• a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (S1 ^a ), preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, 1- ( 2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (S1-1) ("mefenpyr-diethyl"), and related compounds as described in U.S. Pat WO-A-91/07874 are described;
• b) dichlorophenylpyrazolecarboxylic acid derivatives (S1 ^b), preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate (S1-2), 1- (2,4-dichlorophenyl) -5- isopropyl-pyrazole-3-carboxylic acid ethyl ester (S1-3), 1- (2,4-dichlorophenyl) -5- (1,1-dimethyl-ethyl) -pyrazole-3-carboxylic acid ethyl ester (S1-4) and related compounds, as they are in EP-A-333,131 and EP-A-269806 are described;
• c () derivatives of the 1,5-diphenylpyrazole-3-carboxylic acid S1 ^c), preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S1-5), 1- (2-chlorophenyl ) -5-phenylpyrazole-3-carboxylic acid methyl ester (S1-6) and related compounds as described for example in the EP-A-268554 are described;
• d) compounds of the type of the triazolecarboxylic acids (S1 ^d ), preferably compounds such as fenchlorazole (ethyl ester), ie 1- (2,4-dichlorophenyl) -5-trichloromethyl- (1H) -1,2,4-triazole-3- Carboxylic acid ethyl ester (S1-7), and related compounds as in EP-A-174 562 and EP-A-346 620 are described;
• e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 ^e), preferably compounds such as 5- (2, 4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (S1-8) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds as described in U.S. Pat WO-A-91/08202 or 5,5-diphenyl-2-isoxazoline-carboxylic acid (S1-10) or 5,5-diphenyl-2-isoxazoline-carboxylic acid ethyl ester (S1-11) ("isoxadifen-ethyl") or n-propyl ester (S1-12) or 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-13), as described in the patent application WO-A-95/07897 are described.

wobei die Symbole und Indizes folgende Bedeutungen haben:
R_B ¹ ist Halogen, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, Nitro oder (C₁-C₄)Haloalkyl;
n_B ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3;
R_B ² ist OR_B ³, SR_B ³ oder NR_B ³R_B ⁴ oder ein gesättigter
oder ungesättigter 3- bis 7-gliedriger Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonylgruppe in (S2) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel OR_B ³, NHR_B ⁴ oder N(CH₃)₂, insbesondere der Formel OR_B ³;
R_B ³ ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C-Atomen;
R_B ⁴ ist Wasserstoff, (C₁-C₆)Alkyl, (C₁-C₆)Alkoxy oder substituiertes oder unsubstituiertes Phenyl;
T_B ist eine (C₁ oder C₂)-Alkandiylkette, die unsubstituiert oder mit einem oder zwei (C₁-C₄)Alkylresten oder mit [(C₁-C₃)-Alkoxy]-carbonyl substituiert ist;
vorzugsweise:

• a) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2^a), vorzugsweise (5-Chlor-8-chinolinoxy)essigsäure-(1-methylhexyl)ester ("Cloquintocet-mexyl") (S2-1), (5-Chlor-8-chinolinoxy)essigsäure-(1,3-dimethyl-but-1-yl)ester (S2-2), (5-Chlor-8-chinolinoxy)essigsäure-4-allyloxy-butylester (S2-3), (5-Chlor-8-chinolinoxy)essigsäure-1-allyloxy-prop-2-ylester (S2-4), (5-Chlor-8-chinolinoxy)essigsäureethylester (S2-5), (5-Chlor-8-chinolinoxy)essigsäuremethylester (S2-6), (5-Chlor-8-chinolinoxy)essigsäureallylester (S2-7), (5-Chlor-8-chinolinoxy)essigsäure-2-(2-propyliden-iminoxy)-1-ethylester (S2-8), (5-Chlor-8-chinolinoxy)essigsäure-2-oxo-prop-1-ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86 750 , EP-A-94 349 und EP-A-191 736 oder EP-A-0 492 366 beschrieben sind, sowie (5-Chlor-8-chinolinoxy)essigsäure (S2-10), deren Hydrate und Salze, beispielsweise deren Lithium-, Natrium- Kalium-, Kalzium-, Magnesium-, Aluminium-, Eisen-, Ammonium-, quartäre Ammonium-, Sulfonium-, oder Phosphoniumsalze wie sie in der WO-A-2002/34048 beschrieben sind;
• b) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2^b), vorzugsweise Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester, (5-Chlor-8-chinolinoxy)malonsäurediallylester, (5-Chlor-8-chinolinoxy)malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind.

S2) quinoline derivatives of the formula (S2)

where the symbols and indices have the following meanings:
R _B ¹ is halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, nitro or (C ₁ -C ₄ ) haloalkyl;
n _B is a natural number from 0 to 5, preferably 0 to 3;
R _B ² is OR _B ³ , SR _B ³ or NR _B ³ R _B ⁴ or a saturated one
or unsaturated 3- to 7-membered heterocycle having at least one N-atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N-atom with the carbonyl group in (S2) and unsubstituted or by radicals the group is (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy or optionally substituted phenyl, preferably a radical of the formula OR _B ³ , NHR _B ⁴ or N (CH ₃ ) ₂ , in particular of the formula OR _B ³ ;
R _B ³ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
R _B ⁴ is hydrogen, (C ₁ -C ₆ ) alkyl, (C ₁ -C ₆ ) alkoxy or substituted or unsubstituted phenyl;
T _B is a (C ₁ or C ₂ ) alkanediyl chain which is unsubstituted or substituted by one or two (C ₁ -C ₄ ) alkyl radicals or by [(C ₁ -C ₃ ) alkoxy] carbonyl;
preferably:

• a) compounds of the 8-quinolinoxyacetic acid type (S2 ^a ), preferably (5-chloro-8-quinolinoxy) acetic acid (1-methylhexyl) ester ("cloquintocet-mexyl") (S2-1), (5-chloro 8-quinolinoxy) acetic acid (1,3-dimethyl-but-1-yl) ester (S2-2), (5-chloro-8-quinolinoxy) acetic acid 4-allyloxy-butyl ester (S2-3), (5 Chloro-8-quinolinoxy) acetic acid 1-allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinolinoxy) acetic acid ethyl ester (S2-5), (5-chloro-8-quinolinoxy) acetic acid methyl ester (S2-6), (5-chloro-8-quinolinoxy) allyl acetate (S2-7), (5-chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (S2-8 ), (5-chloro-8-quinolinoxy) acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds as described in U.S. Pat EP-A-86,750 . EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366 and (5-chloro-8-quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts as described in US Pat WO-A-2002/34048 are described;
• b) compounds of the (5-chloro-8-quinolinoxy) malonic acid type (S2 ^b ), preferably compounds such as diethyl (5-chloro-8-quinolinoxy) malonate, (5-chloro-8-quinolinoxy) malonic acid, (5-chloro -8-quinolinoxy) malonic acid methyl ethyl ester and related compounds as described in U.S. Pat EP-A-0 582 198 are described.

wobei die Symbole und Indizes folgende Bedeutungen haben:
R_C ¹ ist (C₁-C₄)Alkyl, (C₁-C₄)Haloalkyl, (C₂-C₄)Alkenyl, (C₂-C₄)Haloalkenyl, (C₃-C₇)Cycloalkyl, vorzugsweise Dichlormethyl;
R_C ², R_C ³ sind gleich oder verschieden Wasserstoff, (C₁-C₄)Alkyl, (C₂-C₄)Alkenyl, (C₂-C₄)Alkinyl, (C₁-C₄)Haloalkyl, (C₂-C₄)Haloalkenyl, (C₁-C₄)Alkylcarbamoyl-(C₂-C₄)alkyl, (C₂-C₄)Alkenylcarbamoyl-(C₁-C₄)alkyl, (C₁-C₄)Alkoxy-(C₁-C₄)alkyl, Dioxolanyl-(C₁-C₄)alkyl, Thiazolyl, Furyl, Furylalkyl, Thienyl, Piperidyl, substituiertes oder unsubstituiertes Phenyl, oder R_C ² und R_C ³ bilden zusammen einen substituierten oder unsubstituierten heterocyclischen Ring, vorzugsweise einen Oxazolidin-, Thiazolidin-, Piperidin-, Morpholin-, Hexahydropyrimidin- oder Benzoxazinring;
vorzugsweise:
Wirkstoffe vom Typ der Dichloracetamide, die häufig als Vorauflaufsafener (bodenwirksame Safener) angewendet werden, wie z. B.
"Dichlormid" (N,N-Diallyl-2,2-dichloracetamid) (S3-1),
"R-29148" (3-Dichloracetyl-2,2,5-trimethyl-1,3-oxazolidin) der Firma Stauffer (S3-2),
"R-28725" (3-Dichloracetyl-2,2,-dimethyl-1,3-oxazolidin) der Firma Stauffer (S3-3),
"Benoxacor" (4-Dichloracetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazin) (S3-4),
"PPG-1292" (N-Allyl-N-[(1,3-dioxolan-2-yl)-methyl]-dichloracetamid) der Firma PPG Industries (S3-5),
"DKA-24" (N-Allyl-N-[(allylaminocarbonyl)methyl]-dichloracetamid) der Firma Sagro-Chem (S3-6),
"AD-67" oder "MON 4660" (3-Dichloracetyl-1-oxa-3-aza-spiro[4,5]decan) der Firma Nitrokemia bzw. Monsanto (S3-7),
"TI-35" (1-Dichloracetyl-azepan) der Firma TRI-Chemical RT (S3-8),
"Diclonon" (Dicyclonon) oder "BAS145138" oder "LAB145138" (S3-9) (3-Dichloracetyl-2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonan) der Firma BASF,
"Furilazol" oder "MON 13900" ((RS)-3-Dichloracetyl-5-(2-furyl)-2,2-dimethyloxazolidin) (S3-10); sowie dessen (R)-Isomer (S3-11).S3) compounds of the formula (S3)

where the symbols and indices have the following meanings:
R _C ¹ is (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) haloalkenyl, (C ₃ -C ₇ ) cycloalkyl, preferably dichloromethyl;
R _C ² , R _C ³ are identical or different hydrogen, (C ₁ -C ₄ ) alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, (C ₁ -C ₄ ) haloalkyl, ( C ₂ -C ₄ ) haloalkenyl, (C ₁ -C ₄ ) alkylcarbamoyl (C ₂ -C ₄ ) alkyl, (C ₂ -C ₄ ) alkenylcarbamoyl (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) Alkoxy- (C ₁ -C ₄ ) alkyl, dioxolanyl- (C ₁ -C ₄ ) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R _C ² and R _C ³ together form a substituted one or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring;
preferably:
Active substances of the dichloroacetamide type, which are often used as pre-emergence safeners (soil-active safeners), such as. B.
"Dichloromid" (N, N-diallyl-2,2-dichloroacetamide) (S3-1),
"R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),
"R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
"Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
"PPG-1292" (N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide) from PPG Industries (S3-5),
"DKA-24" (N-allyl-N - [(allylaminocarbonyl) methyl] -dichloroacetamide) from Sagro-Chem (S3-6),
"AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) from Nitrokemia or Monsanto (S3-7),
"TI-35" (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
"Diclonone" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9) (3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo [4.3.0] nonane) from BASF,
"Furilazole" or "MON 13900" ((RS) -3-dichloroacetyl-5- (2-furyl) -2,2-dimethyloxazolidine) (S3-10); and its (R) isomer (S3-11).

worin die Symbole und Indizes folgende Bedeutungen haben:
X_D ist CH oder N;
R_D ¹ ist CO-NR_D ⁵R_D ⁶ oder NHCO-R_D ⁷;
R_D ² ist Halogen, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy, Nitro, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Alkylsulfonyl, (C₁-C₄)Alkoxycarbonyl oder (C₁-C₄)Alkylcarbonyl;
R_D ³ ist Wasserstoff, (C₁-C₄)Alkyl, (C₂-C₄)Alkenyl oder (C₂-C₄)Alkinyl;
R_D ⁴ ist Halogen, Nitro, (C₁-C₄)Alkyl, (C₁-C₄)Haloalkyl, (C₁-C₄)Haloalkoxy, (C₃-C₆)Cycloalkyl, Phenyl, (C₁-C₄)Alkoxy, Cyano, (C₁-C₄)Alkylthio, (C₁-C₄)Alkylsulfinyl, (C₁-C₄)Alkylsulfonyl, (C₁-C₄)Alkoxycarbonyl oder (C₁-C₄)Alkylcarbonyl;
R_D ⁵ ist Wasserstoff, (C₁-C₆)Alkyl, (C₃-C₆)Cycloalkyl, (C₂-C₆)Alkenyl, (C₂-C₆)Alkinyl, (C₅-C₆)Cycloalkenyl, Phenyl oder 3- bis 6-gliedriges Heterocyclyl enthaltend v_D Heteroatome aus der Gruppe Stickstoff, Sauerstoff und Schwefel, wobei die sieben letztgenannten Reste durch v_D Substituenten aus der Gruppe Halogen, (C₁-C₆)Alkoxy, (C₁-C₆)Haloalkoxy, (C₁-C₂)Alkylsulfinyl, (C₁-C₂)Alkylsulfonyl, (C₃-C₆)Cycloalkyl, (C₁-C₄)Alkoxycarbonyl, (C₁-C₄)Alkylcarbonyl und Phenyl und im Falle cyclischer Reste auch (C₁-C₄)Alkyl und (C₁-C₄)Haloalkyl substituiert sind;
R_D ⁶ ist Wasserstoff, (C₁-C₆)Alkyl, (C₂-C₆)Alkenyl oder (C₂-C₆)Alkinyl, wobei die drei letztgenannten Reste durch v_D Reste aus der Gruppe Halogen, Hydroxy, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy und (C₁-C₄)Alkylthio substituiert sind, oder
R_D ⁵ und R_D ⁶ gemeinsam mit dem dem sie tragenden Stickstoffatom einen Pyrrolidinyl- oder Piperidinyl-Rest bilden;
R_D ⁷ ist Wasserstoff, (C₁-C₄)Alkylamino, Di-(C₁-C₄)alkylamino, (C₁-C₆)Alkyl, (C₃-C₆)Cycloalkyl, wobei die 2 letztgenannten Reste durch v_D Substituenten aus der Gruppe Halogen, (C₁-C₄)Alkoxy, (C₁-C₆)Haloalkoxy und (C₁-C₄)Alkylthio und im Falle cyclischer Reste auch (C₁-C₄)Alkyl und (C₁-C₄)Haloalkyl substituiert sind;
n_D ist 0, 1 oder 2;
m_D ist 1 oder 2;
v_D ist 0, 1, 2 oder 3;
davon bevorzugt sind Verbindungen von Typ der N-Acylsulfonamide, z. B. der nachfolgenden Formel (S4^a), die z. B. bekannt sind aus WO-A-97/45016

worin
R_D ⁷ (C₁-C₆)Alkyl, (C₃-C₆)Cycloalkyl, wobei die 2 letztgenannten Reste durch v_D Substituenten aus der Gruppe Halogen, (C₁-C₄)Alkoxy, (C₁-C₆)Haloalkoxy und (C₁-C₄)Alkylthio und im Falle cyclischer Reste auch (C₁-C₄)Alkyl und (C₁-C₄)Haloalkyl substituiert sind;
R_D ⁴ Halogen, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, CF₃;
m_D 1 oder 2;
v_D ist 0, 1, 2 oder 3 bedeutet;
sowie
Acylsulfamoylbenzoesäureamide, z. B. der nachfolgenden Formel (S4^b), die z. B. bekannt sind aus WO-A-99/16744 ,

z. B. solche worin
R_D ⁵ = Cyclopropyl und (R_D ⁴) = 2-OMe ist ("Cyprosulfamide", S4-1),
R_D ⁵ = Cyclopropyl und (R_D ⁴) = 5-Cl-2-OMe ist (S4-2),
R_D ⁵ = Ethyl und (R_D ⁴) = 2-OMe ist (S4-3),
R_D ⁵ = Isopropyl und (R_D ⁴) = 5-Cl-2-OMe ist (S4-4) und
R_D ⁵ = Isopropyl und (R_D ⁴) = 2-OMe ist (S4-5).
sowie
Verbindungen vom Typ der N-Acylsulfamoylphenylharnstoffe der Formel (S4^c), die z. B. bekannt sind aus der EP-A-365484 ,

worin
R_D ⁸ und R_D ⁹ unabhängig voneinander Wasserstoff, (C₁-C₈)Alkyl, (C₃-C₈)Cycloalkyl, (C₃-C₆)Alkenyl, (C₃-C₆)Alkinyl,
R_D ⁴ Halogen, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, CF₃
m_D 1 oder 2 bedeutet;
beispielsweise
1-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylharnstoff,
1-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylharnstoff,
1-[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylharnstoff.S4) N-acylsulfonamides of the formula (S4) and their salts,

wherein the symbols and indices have the following meanings:
X _D is CH or N;
R _D ¹ is CO-NR _D ⁵ R _D ⁶ or NHCO-R _D ⁷ ;
R _D ² is halogen, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) haloalkoxy, nitro, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) Alkylsulfonyl, (C ₁ -C ₄ ) alkoxycarbonyl or (C ₁ -C ₄ ) alkylcarbonyl;
R _D ³ is hydrogen, (C ₁ -C ₄ ) alkyl, (C ₂ -C ₄ ) alkenyl or (C ₂ -C ₄ ) alkynyl;
R _D ⁴ is halogen, nitro, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) haloalkoxy, (C ₃ -C ₆ ) cycloalkyl, phenyl, (C ₁ - C ₄ ) alkoxy, cyano, (C ₁ -C ₄ ) alkylthio, (C ₁ -C ₄ ) alkylsulfinyl, (C ₁ -C ₄ ) alkylsulfonyl, (C ₁ -C ₄ ) alkoxycarbonyl or (C ₁ -C ₄ ) alkylcarbonyl;
R _D ⁵ is hydrogen, (C ₁ -C ₆ ) alkyl, (C ₃ -C ₆ ) cycloalkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) alkynyl, (C ₅ -C ₆ ) cycloalkenyl , Phenyl or 3- to 6-membered heterocyclyl containing v _D heteroatoms from the group consisting of nitrogen, oxygen and sulfur, where the seven latter radicals are represented by v _D substituents from the group halogen, (C ₁ -C ₆ ) alkoxy, (C ₁ - C ₆ ) haloalkoxy, (C ₁ -C ₂ ) alkylsulfinyl, (C ₁ -C ₂ ) alkylsulfonyl, (C ₃ -C ₆ ) cycloalkyl, (C ₁ -C ₄ ) alkoxycarbonyl, (C ₁ -C ₄ ) alkylcarbonyl and Phenyl and in the case of cyclic radicals also (C ₁ -C ₄ ) alkyl and (C ₁ -C ₄ ) haloalkyl;
R _D ⁶ is hydrogen, (C ₁ -C ₆ ) alkyl, (C ₂ -C ₆ ) alkenyl or (C ₂ -C ₆ ) alkynyl, where the three last-mentioned radicals are represented by v _D radicals from the group consisting of halogen, hydroxy, ( C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy and (C ₁ -C ₄ ) alkylthio, or
R _D ⁵ and R _D ⁶ together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;
R _D ⁷ is hydrogen, (C ₁ -C ₄ ) alkylamino, di- (C ₁ -C ₄ ) alkylamino, (C ₁ -C ₆ ) alkyl, (C ₃ -C ₆ ) cycloalkyl, wherein the latter two radicals by v _D substituents from the group halogen, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₆ ) haloalkoxy and (C ₁ -C ₄ ) alkylthio and in the case of cyclic radicals also (C ₁ -C ₄ ) alkyl and ( C ₁ -C ₄ ) haloalkyl are substituted;
n _D is 0, 1 or 2;
m _D is 1 or 2;
v _D is 0, 1, 2 or 3;
preferred are compounds of the type of N-acylsulfonamides, e.g. B. the following formula (S4 ^a ), z. B. are known WO 97/45016

wherein
R _D ⁷ (C ₁ -C ₆ ) alkyl, (C ₃ -C ₆ ) cycloalkyl, where the 2 last-mentioned radicals by v _D substituents from the group halogen, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₆ ) Haloalkoxy and (C ₁ -C ₄ ) alkylthio and in the case of cyclic radicals also (C ₁ -C ₄ ) alkyl and (C ₁ -C ₄ ) haloalkyl;
R _D ^{4 is} halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, CF ₃ ;
m _D 1 or 2;
v _D is 0, 1, 2 or 3;
such as
Acylsulfamoylbenzoic acid amides, e.g. B. the following formula (S4 ^b ), the z. B. are known WO-A-99/16744 .

z. For example, such
R _D ⁵ = cyclopropyl and (R _D ⁴ ) = 2-OMe ("Cyprosulfamide", S4-1),
R _D ⁵ = cyclopropyl and (R _D ⁴ ) = 5-Cl-2-OMe is (S4-2),
R _D ⁵ = ethyl and (R _D ⁴ ) = 2-OMe is (S4-3),
R _D ⁵ = isopropyl and (R _D ⁴ ) = 5-Cl-2-OMe is (S4-4) and
R _D ⁵ = isopropyl and (R _D ⁴ ) = 2-OMe is (S4-5).
such as
Compounds of the type of N-acylsulfamoylphenylureas of the formula (S4 ^c ), which are described, for example, in US Pat. B. are known from the EP-A-365484 .

wherein
R _D ⁸ and R _D ⁹ are each independently hydrogen, (C ₁ -C ₈ ) alkyl, (C ₃ -C ₈ ) cycloalkyl, (C ₃ -C ₆ ) alkenyl, (C ₃ -C ₆ ) alkynyl,
R _D ^{4 is} halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, CF ₃
m is _D 1 or 2;
for example
1- [4- (N-2-Methoxybenzoylsulfamoyl) phenyl] -3-methyl-urea,
1- [4- (N-2-Methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
1- [4- (N-4,5-Dimethylbenzoylsulfamoyl) phenyl] -3-methyl-urea.

S5) active substances from the class of hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), z. B. 3,4,5-Triacetoxybenzoesäureethylester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-Fluorsalicyclsäure, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in the WO-A-2004/084631 . WO-A-2005/015994 . WO-A-2005/016001 are described.

S6) active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), z. For example, 1-methyl-3- (2-thienyl) -1,2-dihydroquinoxalin-2-one, 1-methyl-3- (2-thienyl) -1,2-dihydroquinoxaline-2-thione, 1- (2 -Aminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxaline-2-one hydrochloride, 1- (2-methylsulphonylaminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxaline 2-on, as in the WO 2005/112630 are described.

worin die Symbole und Indizes folgende Bedeutungen haben:
R_E ¹, R_E ² sind unabhängig voneinander Halogen, (C₁-C₄)Alkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Haloalkyl, (C₁-C₄)Alkylamino, Di-(C₁-C₄)Alkylamino, Nitro;
A_E ist COOR_E ³ oder COSR_E ⁴
R_E ³, R_E ⁴ sind unabhängig voneinander Wasserstoff, (C₁-C₄)Alkyl, (C₂-C₆)Alkenyl, (C₂-C₄)Alkinyl, Cyanoalkyl, (C₁-C₄)Haloalkyl, Phenyl, Nitrophenyl, Benzyl, Halobenzyl, Pyridinylalkyl und Alkylammonium,
n_E ¹ ist 0 oder 1
n_E ², n_E ³ sind unabhängig voneinander 0, 1 oder 2,
vorzugsweise:
Diphenylmethoxyessigsäure,
Diphenylmethoxyessigsäureethylester,
Diphenylmethoxyessigsäuremethylester (CAS-Reg. Nr. 41858-19-9) (S7-1).S7) compounds of the formula (S7), as described in the WO-A-1998/38856 are described

wherein the symbols and indices have the following meanings:
R _E ¹ , R _E ² are each independently halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkylamino, di (C ₁ -C ₄ ) alkylamino, nitro;
A _E is COOR _E ³ or COSR _E ⁴
R _E ³ , R _E ⁴ are each independently hydrogen, (C ₁ -C ₄ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₄ ) alkynyl, cyanoalkyl, (C ₁ -C ₄ ) haloalkyl, Phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium,
n _E ¹ is 0 or 1
n _E ² , n _E ³ are each independently 0, 1 or 2,
preferably:
diphenylmethoxy,
Diphenylmethoxyessigsäureethylester,
Methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1).

worin
X_F CH oder N,
n_F für den Fall, dass X_F=N ist, eine ganze Zahl von 0 bis 4 und
für den Fall, dass X_F=CH ist, eine ganze Zahl von 0 bis 5,
R_F ¹ Halogen, (C₁-C₄)Alkyl, (C₁-C₄)Haloalkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Haloalkoxy, Nitro, (C₁-C₄)Alkylthio, (C₁-C₄)-Alkylsulfonyl, (C₁-C₄)Alkoxycarbonyl, ggf. substituiertes. Phenyl, ggf. substituiertes Phenoxy,
R_F ² Wasserstoff oder (C₁-C₄)Alkyl
R_F ³ Wasserstoff, (C₁-C₈)Alkyl, (C₂-C₄)Alkenyl, (C₂-C₄)Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist; bedeuten, oder deren Salze,
vorzugsweise Verbindungen worin
X_F CH,
n_F eine ganze Zahl von 0 bis 2,
R_F ¹ Halogen, (C₁-C₄)Alkyl, (C₁-C₄)Haloalkyl, (C₁-C₄)Alkoxy, (C₁-C₄)Haloalkoxy,
R_F ² Wasserstoff oder (C₁-C₄)Alkyl,
R_F ³ Wasserstoff, (C₁-C₈)Alkyl, (C₂-C₄)Alkenyl, (C₂-C₄)Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist, bedeuten, oder deren Salze.S8) compounds of the formula (S8) as described in the WO-A-98/27049 are described

wherein
X _F CH or N,
n _F for the case that X _F = N, an integer from 0 to 4 and
for the case that X _F = CH, an integer from 0 to 5,
R _F ^{1 is} halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy, nitro, (C ₁ -C ₄ ) Alkylthio, (C ₁ -C ₄ ) alkylsulfonyl, (C ₁ -C ₄ ) alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy,
R _F ^{2 is} hydrogen or (C ₁ -C ₄ ) alkyl
R _F ^{3 is} hydrogen, (C ₁ -C ₈ ) alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or substituted by one or more preferably up to three identical or different radicals from the group consisting of halogen and alkoxy substituted; mean, or their salts,
preferably compounds wherein
X _F CH,
n _{F is} an integer from 0 to 2,
R _F ^{1 is} halogen, (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) haloalkyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) haloalkoxy,
R _F ^{2 is} hydrogen or (C ₁ -C ₄ ) alkyl,
R _F ^{3 is} hydrogen, (C ₁ -C ₈ ) alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or substituted by one or more preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted, mean, or their salts.

S9) agents from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), z. 1,2-dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy 1-methyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS reg. No. 95855-00-8) as described in the WO-A-1999/000020 are described.

worin
R_G ¹ Halogen, (C₁-C₄)Alkyl, Methoxy, Nitro, Cyano, CF₃, OCF₃
Y_G, Z_G unabhängig voneinander O oder S,
n_G eine ganze Zahl von 0 bis 4,
R_G ² (C₁-C₁₆)Alkyl, (C₂-C₆)Alkenyl, (C₃-C₆)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl,
R_G ³ Wasserstoff oder (C₁-C₆)Alkyl bedeutet.S10) Compounds of the formulas (S10 ^a ) or (S10 ^b )
as they are in the WO-A-2007/023719 and WO-A-2007/023764 are described

wherein
R _G ^{1 is} halogen, (C ₁ -C ₄ ) alkyl, methoxy, nitro, cyano, CF ₃ , OCF ₃
Y _G , Z _G independently of one another O or S,
n _{G is} an integer from 0 to 4,
R _G ² (C ₁ -C ₁₆ ) alkyl, (C ₂ -C ₆ ) alkenyl, (C ₃ -C ₆ ) cycloalkyl, aryl; Benzyl, halobenzyl,
R _G ^{3 is} hydrogen or (C ₁ -C ₆ ) alkyl.

S11) oxyimino compound type compounds (S11) known as seed dressings, such as those described in US Pat. B.
"Oxabetrinil" ((Z) -1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S11-1), which is known as a seed dressing safener for millet against damage by metolachlor,
"Fluxofenim" (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) oxime) (S11-2) which was used as seed dressing Safener for millet is known against damage from metolachlor, and
"Cyometrinil" or "CGA-43089" ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (S11-3), which is known as a seed dressing safener for millet against damage by metolachlor.

S12) active substances from the class of isothiochromanones (S12), such as. Methyl [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds WO-A-1998/13361 ,

S13) One or more compounds from group (S13):
"Naphthalene anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides
"Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as safener for pretilachlor in sown rice,
"Flurazole" (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seeder-safener for millet against damage by alachlor and metolachlor,
"CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as Safener for maize is known against damage from imidazolinones,
"MG 191" (CAS reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn,
"MG-838" (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) from Nitrokemia,
"Disulfonone" (O, O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),
"Dietholate" (O, O-diethyl-O-phenyl phosphorotioate) (S13-8),
"Mephenate" (4-chlorophenyl methylcarbamate) (S13-9).

S14) active substances, in addition to a herbicidal activity against harmful plants and safener action on crop plants such as rice, such as. B.
"Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethyl-piperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide Molinate,
"Daimuron" or "SK 23" (1- (1-methyl-1-phenylethyl) -3-p-tolyl-urea) known as safener for rice against damage of the herbicide imazosulfuron,
"Cumyluron" = "JC-940" (3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) urea, see JP-A-60087254 ), which is known as a safener for rice against damage of some herbicides,
"Methoxyphenone" or "NK 049"(3,3'-dimethyl-4-methoxy-benzophenone), which is known as safener for rice against damage of some herbicides,
"COD" (1-bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as safener against damage of some herbicides in rice.

S15) active substances, which are used primarily as herbicides, but also have safener effect on crop plants, eg. B.
(2,4-dichlorophenoxy) acetic acid (2,4-D),
(4-chlorophenoxy) acetic acid,
(R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop),
4- (2,4-dichlorophenoxy) butyric acid (2,4-DB),
(4-chloro-o-tolyloxy) acetic acid (MCPA),
4- (4-chloro-o-tolyloxy) butyric acid,
4- (4-chlorophenoxy) butyric acid,
3,6-dichloro-2-methoxybenzoic acid (Dicamba),
1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloroethyl).

Prefers are herbicide-safener combinations containing (A) a herbicide effective amount of one or more compounds of the formula (I) or their salts, and (B) an antidote effective amount of one or more safeners.

herbicide effective amount means for the purposes of the invention an amount of a or more herbicides that is suitable, the plant growth negative to influence. Antidote effective amount means in the sense of Invention an amount of one or more safeners that are suitable is the phytotoxic effect of pesticide active ingredients (eg of herbicides) to crops.

Some The safeners are already known as herbicides and thus develop in addition to the herbicidal action in harmful plants at the same time also protective effect at the crops.

The weight ratios of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the particular safener and may vary within wide limits for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20. The safeners can be formulated analogously to the compounds of the formula (I) or mixtures thereof with further herbicides / pesticides and provided and used as finished formulation or tank mixture with the herbicides.

to Application will be in commercial form If appropriate, formulations are diluted in the customary manner z. As in wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Powdery Preparations, ground or spreading granules and sprayable Solutions become common before application no longer diluted with other inert substances.

With external conditions such as temperature, humidity, the type of herbicide used, u. a. varies the required Application rate of the compounds of general formula (I). she can vary within wide limits, z. B. between 0.001 and 10.0 kg / ha or more of active substance, but is preferably between 0.005 and 5 kg / ha.

The The present invention will be more apparent from the following examples which, however, by no means limit the invention.

A. Synthesis Examples

1. N - [(4-Chloro-6-methoxy-pyrimidin-2-yl) carbamoyl] -3- (4,5-dihydroisoxazol-3-yl) -pyridine-2-sulfonamide (Ia-1):

230 mg (1 mmol) of 3- (4,5-dihydroisoxazol-3-yl) -pyridine-2-sulfonamide (IIa-1) are dissolved in 10 ml of acetonitrile and treated with 400 mg (1 mmol) of diphenyl- (4-chloro) 6-methoxypyrimidin-2-yl) imidodicarbonate (cf. WO 1996/022284 ). With stirring, 160 mg (1 mmol) of DBU (diazabicyclo-undecene) are added dropwise. After standing for 1 hour at 20 ° C is poured onto a mixture of methylene chloride and aqueous hydrochloric acid (5%). The organic phase is washed twice with water and once with saturated brine. After drying with magnesium sulfate, the organic phase is concentrated in vacuo. The residue is triturated in diethyl ether and filtered off with suction. The resulting crystals are stirred in isopropanol, filtered off with suction and dried. 200 mg (0.45 mmol) of N - [(4-chloro-6-methoxypyrimidin-2-yl) carbamoyl] -3- (4,5-dihydroisoxazol-3-yl) pyridine-2-sulfonamide (Ia-1) are obtained. from the purity content (HPLC) 92.8%.

¹H-NMR-Daten (400 MHz., Solvens: CD₃CN, interner Standard: Tetramethylsilan δ = 0.00 ppm; s = Singulett, br. s = breites Singulett, d = Dublett, dd = Doppeldublett, m = Multiplett, q = Quartett, t = Triplett)

Ia-1: δ = 3.44 (t, 2H); 4.01 (s, 6H); 4.47 (t, 2H); 6.62 (s, 1H); 7.68 (dd, 1H); 7.99 (dd, 1H); 8.39 (br. s, 1H); 8.68 (dd, 1H); 12.2 (br. s, 1H) ppm
Ia-2: δ = 3.44 (t, 2H); 3.94 (s, 6H); 4.46 (t, 2H); 5.87 (s, 1H); 7.67 (dd, 1H); 7.98 (dd, 1H); 8.14 (br. s, 1H); 8.66 (dd, 1H); 12.8 (br. s, 1H) ppm
Ia-3: δ = 2.42 (s, 6H); 3.45 (t, 2H); 4.46 (t, 2H); 6.90 (s, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.06 (br. s, 1H); 8.66 (dd, 1H); 13.3 (br. s, 1H) ppm
Ia-4: δ = 2.55 (s, 3H); 3.45 (t, 2H); 3.94 (s, 3H); 4.47 (t, 2H); 6.42 (s, 1H); 7.67 (dd, 1H); 7.98 (dd, 1H); 8.18 (br. s, 1H); 8.67 (dd, 1H); 12.9 (br. s, 1H) ppm
Ia-5: δ = 3.45 (t, 2H); 3.97 (s, 3H); 4.46 (t, 2H); 6.54 (d, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.1-8.4 (br. 1H); 8.29 (d, 1H); 8.66 (dd, 1H); 13.1 (br. s, 1H) ppm
Ia-6: δ = 3.44 (t, 2H); 4.03 (s, 6H); 4.47 (t, 2H); 7.68 (dd, 1H); 7.99 (dd, 1H); 8.4 (br. s, 1H); 8.67 (dd, 1H); 12.5 (br. s, 1H) ppm
Ia-7: δ = 2.49 (s, 3H); 3.44 (t, 2H); 4.02 (s, 3H); 4.47 (t, 2H); 7.68 (dd, 1H); 8.00 (dd, 1H); 8.4 (br., 1H); 8.67 (dd, 1H); 12.6 (br. s, 1H) ppm
Ia-8: δ = 3.16 (s, 3H); 3.19 (s, 3H); 3.44 (t, 2H); 4.47 (t, 2H); 4.87 (q, 2H); 7.67 (dd, 1H); 7.98 (dd, 1H); 8.14 (br. s, 1H); 8.67 (dd, 1H); 12.9 (br. s, 1H) ppm
Ia-9: δ = 3.43 (s, 3H); 3.45 (t, 2H); 3.95 (s, 3H); 4.46 (t, 2H); 6.40 (s, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.0-8.25 (br., 1H); 8.66 (dd, 1H); 13.4 (br. s, 1H) ppm
Ia-10: δ = 0.95 (d, 3H); 1.01 (d, 3H); 3.18 (dd, 1H); 3.45 (dd, 1H); 3.87 (m, 1H); 3.94 (s, 6H); 4.49 (m, 1H); 5.86 (s, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.2 (br. s, 1H); 8.65 (dd, 1H); 12.8 (br. s, 1H) ppm
Ia-11: δ = 1.40 (d, 3H); 3.07 (dd, 1H); 3.54 (dd, 1H); 3.94 (s, 6H); 4.89 (m, 1H); 5.87 (s, 1H); 7.66 (dd, 1H); 7.98 (dd, 1H); 8.18 (br. s, 1H); 8.65 (dd, 1H); 12.8 (br. s, 1H) ppm
Ia-12: δ = 1.47 (s, 6H); 2.49 (s, 3H); 3.24 (s, 2H); 4.02 (s, 3H); 7.67 (dd, 1H); 7.99 (dd, 1H); 8.45 (br. s, 1H); 8.64 (dd, 1H); 12.6 (br. s, 1H) ppm
Ia-13: δ = 1.47 (s, 6H); 3.25 (s, 2H); 3.94 (s, 6H); 5.86 (s, 1H); 7.66 (dd, 1H); 7.99 (dd, 1H); 8.16 (br. s, 1H); 8.64 (dd, 1H); 12.8 (br. s, 1H) ppm
Ia-14: δ = 1.47 (s, 6H); 3.25 (s, 2H); 4.00 (s, 3H); 6.61 (s, 1H); 7.67 (dd, 1H); 7.99 (dd, 1H); 8.38 (br. s, 1H); 8.65 (dd, 1H); 12.2 (br. s, 1H) ppm
Ia-15: δ = 1.40 (d, 3H); 2.39 (s, 3H); 3.08 (dd, 1H); 3.55 (dd, 1H); 3.94 (s, 3H); 4.89 (m, 1H); 6.40 (s, 1H); 7.65 (dd, 1H); 7.96 (dd, 1H); 8.0-8.3 (br., 1H); 8.64 (dd, 1H); 13.4 (br., 1H) ppm
Ia-16: δ = 1.40 (d, 3H); 3.07 (dd, 1H); 3.54 (dd, 1H); 4.01 (s, 3H); 4.90 (m, 1H); 6.62 (s, 1H); 7.67 (dd, 1H); 7.99 (dd, 1H); 8.40 (br. s, 1H); 8.66 (dd, 1H); 12.2 (br. s, 1H) ppm
Ia-17: δ = 0.97 (t, 3H); 1.4-1.55 (m, 2H); 1.6-1.7 (m, 1H); 1.72-1.82 (m, 1H); 2.39 (s, 3H); 3.11 (dd, 1H); 3.51 (dd, 1H); 3.95 (s, 3H); 4.75 (m, 1H); 6.40 (s, 1H); 7.65 (dd, 1H); 7.97 (dd, 1H); 8.05-8.25 (br., 1H); 8.64 (dd, 1H); 13.4 (br. s, 1H) ppm
Ia-18: δ = 0.99 (t, 3H); 1.65-1.85 (m, 2H); 2.50 (s, 3H); 3.11 (dd, 1H); 3.49 (dd, 1H); 4.02 (s, 3H); 4.71 (m, 1H); 7.68 (dd, 1H); 7.99 (dd, 1H); 8.42 (br. s, 1H); 8.66 (dd, 1H); 12.6 (br. s, 1H) ppm
Ia-19: δ = 0.98 (t, 3H); 1.65-1.85 (m, 2H); 2.39 (s, 3H); 3.12 (dd, 1H); 3.51 (dd, 1H); 3.95 (s, 3H); 4.70 (m, 1H); 6.40 (s, 1H); 7.65 (dd, 1H); 7.96 (dd, 1H); 8.13 (br. s, 1H); 8.65 (dd, 1H); 13.4 (br. s, 1H) ppm
Ia-20: δ = 0.99 (t, 3H); 1.65-1.85 (m, 2H); 3.11 (dd, 1H); 3.50 (dd, 1H); 4.01 (s, 3H); 4.70 (m, 1H); 6.62 (s, 1H); 7.67 (dd, 1H); 7.98 (dd, 1H); 8.39 (br. s, 1H); 8.66 (dd, 1H); 12.2 (br. s, 1H) ppm
Ia-21: δ = 0.98 (t, 3H); 1.40-1.55 (m, 2H); 1.6-1.7 (m, 1H); 1.7-1.85 (m. 1H); 3.11 (dd, 1H); 3.51 (dd, 1H); 3.94 (s, 6H); 4.75 (m, 1H); 5.86 (s, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.13 (br. s, 1H); 8.64 (dd, 1H); 12.8 (br. s, 1H) ppm
Ia-22: δ = 0.95 (d, 3H); 1.00 (d, 3H); 2.39 (s, 3H); 3.18 (dd, 1H); 3.46 (dd, 1H); 3.95 (s, 3H); 4.50 (m, 1H); 6.40 (s, 1H); 7.65 (dd, 1H); 7.96 (dd, 1H); 8.05-8.25 (br., 1H); 8.65 (dd, 1H); 13.4 (br. s, 1H) ppm
Ia-23: δ = 0.97 (t, 3H); 1.35-1.55 (m, 2H); 1.6-1.7 (m, 1H); 1.72-1.83 (m, 1H); 2.50 (s, 3H); 3.10 (dd, 1H); 3.50 (dd, 1H); 4.02 (s. 3H); 4.78 (m, 1H); 7.67 (dd, 1H); 7.99 (dd, 1H); 8.44 (br. s, 1H); 8.65 (dd, 1H); 12.6 (br. s, 1H) ppm
Ia-24: δ = 0.98 (t, 3H); 1.63-1.86 (m, 2H); 3.12 (dd, 1H); 3.50 (dd, 1H); 3.94 (s, 6H); 4.70 (m, 1H); 5.87 (s, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.15 (br. s, 1H); 8.65 (dd, 1H); 12.8 (br. s, 1H) ppm

The compounds of general formula (I) described in the following tables are obtained according to or analogously to the synthesis example described above:

¹ H-NMR data (400 MHz., Solvent: CD ₃ CN, internal standard: tetramethylsilane δ = 0.00 ppm; s = singlet, br. S = broad singlet, d = doublet, dd = double doublet, m = multiplet, q = Quartet, t = triplet)

Ia-1: δ = 3.44 (t, 2H); 4.01 (s, 6H); 4.47 (t, 2H); 6.62 (s, 1H); 7.68 (dd, 1H); 7.99 (dd, 1H); 8.39 (brs s, 1H); 8.68 (dd, 1H); 12.2 (br s, 1H) ppm
Ia-2: δ = 3.44 (t, 2H); 3.94 (s, 6H); 4.46 (t, 2H); 5.87 (s, 1H); 7.67 (dd, 1H); 7.98 (dd, 1H); 8.14 (brs s, 1H); 8.66 (dd, 1H); 12.8 (brs s, 1H) ppm
Ia-3: δ = 2.42 (s, 6H); 3.45 (t, 2H); 4.46 (t, 2H); 6.90 (s, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.06 (brs s, 1H); 8.66 (dd, 1H); 13.3 (brs s, 1H) ppm
Ia-4: δ = 2.55 (s, 3H); 3.45 (t, 2H); 3.94 (s, 3H); 4.47 (t, 2H); 6.42 (s, 1H); 7.67 (dd, 1H); 7.98 (dd, 1H); 8.18 (brs s, 1H); 8.67 (dd, 1H); 12.9 (brs s, 1H) ppm
Ia-5: δ = 3.45 (t, 2H); 3.97 (s, 3H); 4.46 (t, 2H); 6.54 (d, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.1-8.4 (br.1H); 8.29 (d, 1H); 8.66 (dd, 1H); 13.1 (brs s, 1H) ppm
Ia-6: δ = 3.44 (t, 2H); 4.03 (s, 6H); 4.47 (t, 2H); 7.68 (dd, 1H); 7.99 (dd, 1H); 8.4 (brs s, 1H); 8.67 (dd, 1H); 12.5 (brs s, 1H) ppm
Ia-7: δ = 2.49 (s, 3H); 3.44 (t, 2H); 4.02 (s, 3H); 4.47 (t, 2H); 7.68 (dd, 1H); 8.00 (dd, 1H); 8.4 (br., 1H); 8.67 (dd, 1H); 12.6 (br s, 1H) ppm
Ia-8: δ = 3.16 (s, 3H); 3.19 (s, 3H); 3.44 (t, 2H); 4.47 (t, 2H); 4.87 (q, 2H); 7.67 (dd, 1H); 7.98 (dd, 1H); 8.14 (brs s, 1H); 8.67 (dd, 1H); 12.9 (brs s, 1H) ppm
Ia-9: δ = 3.43 (s, 3H); 3.45 (t, 2H); 3.95 (s, 3H); 4.46 (t, 2H); 6.40 (s, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.0-8.25 (br., 1H); 8.66 (dd, 1H); 13.4 (brs s, 1H) ppm
Ia-10: δ = 0.95 (d, 3H); 1.01 (d, 3H); 3.18 (dd, 1H); 3.45 (dd, 1H); 3.87 (m, 1H); 3.94 (s, 6H); 4.49 (m, 1H); 5.86 (s, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.2 (brs s, 1H); 8.65 (dd, 1H); 12.8 (brs s, 1H) ppm
Ia-11: δ = 1.40 (d, 3H); 3.07 (dd, 1H); 3.54 (dd, 1H); 3.94 (s, 6H); 4.89 (m, 1H); 5.87 (s, 1H); 7.66 (dd, 1H); 7.98 (dd, 1H); 8.18 (brs s, 1H); 8.65 (dd, 1H); 12.8 (brs s, 1H) ppm
Ia-12: δ = 1.47 (s, 6H); 2.49 (s, 3H); 3.24 (s, 2H); 4.02 (s, 3H); 7.67 (dd, 1H); 7.99 (dd, 1H); 8.45 (brs s, 1H); 8.64 (dd, 1H); 12.6 (br s, 1H) ppm
Ia-13: δ = 1.47 (s, 6H); 3.25 (s, 2H); 3.94 (s, 6H); 5.86 (s, 1H); 7.66 (dd, 1H); 7.99 (dd, 1H); 8.16 (brs s, 1H); 8.64 (dd, 1H); 12.8 (brs s, 1H) ppm
Ia-14: δ = 1.47 (s, 6H); 3.25 (s, 2H); 4.00 (s, 3H); 6.61 (s, 1H); 7.67 (dd, 1H); 7.99 (dd, 1H); 8.38 (brs s, 1H); 8.65 (dd, 1H); 12.2 (br s, 1H) ppm
Ia-15: δ = 1.40 (d, 3H); 2.39 (s, 3H); 3.08 (dd, 1H); 3.55 (dd, 1H); 3.94 (s, 3H); 4.89 (m, 1H); 6.40 (s, 1H); 7.65 (dd, 1H); 7.96 (dd, 1H); 8.0-8.3 (br., 1H); 8.64 (dd, 1H); 13.4 (br., 1H) ppm
Ia-16: δ = 1.40 (d, 3H); 3.07 (dd, 1H); 3.54 (dd, 1H); 4.01 (s, 3H); 4.90 (m, 1H); 6.62 (s, 1H); 7.67 (dd, 1H); 7.99 (dd, 1H); 8.40 (brs s, 1H); 8.66 (dd, 1H); 12.2 (br s, 1H) ppm
Ia-17: δ = 0.97 (t, 3H); 1.4-1.55 (m, 2H); 1.6-1.7 (m, 1H); 1.72-1.82 (m, 1H); 2.39 (s, 3H); 3.11 (dd, 1H); 3.51 (dd, 1H); 3.95 (s, 3H); 4.75 (m, 1H); 6.40 (s, 1H); 7.65 (dd, 1H); 7.97 (dd, 1H); 8.05-8.25 (br., 1H); 8.64 (dd, 1H); 13.4 (brs s, 1H) ppm
Ia-18: δ = 0.99 (t, 3H); 1.65-1.85 (m, 2H); 2.50 (s, 3H); 3.11 (dd, 1H); 3.49 (dd, 1H); 4.02 (s, 3H); 4.71 (m, 1H); 7.68 (dd, 1H); 7.99 (dd, 1H); 8.42 (brs s, 1H); 8.66 (dd, 1H); 12.6 (br s, 1H) ppm
Ia-19: δ = 0.98 (t, 3H); 1.65-1.85 (m, 2H); 2.39 (s, 3H); 3.12 (dd, 1H); 3.51 (dd, 1H); 3.95 (s, 3H); 4.70 (m, 1H); 6.40 (s, 1H); 7.65 (dd, 1H); 7.96 (dd, 1H); 8.13 (brs s, 1H); 8.65 (dd, 1H); 13.4 (brs s, 1H) ppm
Ia-20: δ = 0.99 (t, 3H); 1.65-1.85 (m, 2H); 3.11 (dd, 1H); 3.50 (dd, 1H); 4.01 (s, 3H); 4.70 (m, 1H); 6.62 (s, 1H); 7.67 (dd, 1H); 7.98 (dd, 1H); 8.39 (brs s, 1H); 8.66 (dd, 1H); 12.2 (br s, 1H) ppm
Ia-21: δ = 0.98 (t, 3H); 1.40-1.55 (m, 2H); 1.6-1.7 (m, 1H); 1.7-1.85 (m.l.H); 3.11 (dd, 1H); 3.51 (dd, 1H); 3.94 (s, 6H); 4.75 (m, 1H); 5.86 (s, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.13 (brs s, 1H); 8.64 (dd, 1H); 12.8 (brs s, 1H) ppm
Ia-22: δ = 0.95 (d, 3H); 1.00 (d, 3H); 2.39 (s, 3H); 3.18 (dd, 1H); 3.46 (dd, 1H); 3.95 (s, 3H); 4.50 (m, 1H); 6.40 (s, 1H); 7.65 (dd, 1H); 7.96 (dd, 1H); 8.05-8.25 (br., 1H); 8.65 (dd, 1H); 13.4 (brs s, 1H) ppm
Ia-23: δ = 0.97 (t, 3H); 1.35-1.55 (m, 2H); 1.6-1.7 (m, 1H); 1.72-1.83 (m, 1H); 2.50 (s, 3H); 3.10 (dd, 1H); 3.50 (dd, 1H); 4.02 (see 3H); 4.78 (m, 1H); 7.67 (dd, 1H); 7.99 (dd, 1H); 8.44 (brs s, 1H); 8.65 (dd, 1H); 12.6 (br s, 1H) ppm
Ia-24: δ = 0.98 (t, 3H); 1.63-1.86 (m, 2H); 3.12 (dd, 1H); 3.50 (dd, 1H); 3.94 (s, 6H); 4.70 (m, 1H); 5.87 (s, 1H); 7.66 (dd, 1H); 7.97 (dd, 1H); 8.15 (brs s, 1H); 8.65 (dd, 1H); 12.8 (brs s, 1H) ppm

2. 3- (4,5-Dihydroisoxazol-3-yl) pyridine-2-sulfonamide (IIa-1)

2.7 g (10 mmol) 2- (benzylthio) -3- (4,5-dihydroisoxazol-3-yl) pyridine (Xa-1) are taken up in a mixture of 50 ml of glacial acetic acid and 25 ml of water. In the resulting suspension is introduced at 0 ° C chlorine gas, until a faint yellowing occurs. The clear solution is extracted three times with methylene chloride. The combined organic Phases are washed with water and brine, dried with magnesium sulfate and concentrated in vacuo. It arises as oily substance the compound of formula (VIIIa-1), which is used without further purification in the subsequent reaction.

The crude sulfochloride (VIIIa-1) is taken up in 10 ml of acetonitrile and with 26% aqueous ammonia solution dropwise added until a sample shows basic reaction. The approach becomes concentrated and taken up in methylene chloride. insoluble Salts are filtered off. The filtrate is washed with water, dried and concentrated, the residue triturated with diethyl ether. This gives 1.3 g (5.5 mmol) of 3- (4,5-dihydroisoxazol-3-yl) pyridine-2-sulfonamide (IIa-1) of the purity content (HPLC) 96.1% in the form of colorless crystals, m.p. 155-156 ° C.

Analog can be produced:

3. 2- (Benzylthio) -3- (4,5-dihydroisoxazol-3-yl) pyridine (Xa-1)

In 600 ml of absolute N, N-dimethylformamide are added to 2.86 g (0.11 mol) Sodium hydride (95%) suspended. While stirring added dropwise 13.64 g (0.11 mol) of benzylmercaptan, with heating taking place.

In the clear solution is added in portions 18.3 g (0.1 mol) 2-chloro-3- (4,5-dihydroisoxazol-3-yl) pyridine (XIa-1) in 30 ml of N, N-dimethylformamide, and 3 hours at 20 ° C. stirred. The solution is concentrated, the residue taken up in methylene chloride and washed several times with water. After drying with magnesium sulfate, filter and concentrate the residue crystallizes in diisopropyl ether. You get 23.8 g (87.4 mmol) of 2- (benzylthio) -3- (4,5-dihydroisoxazol-3-yl) pyridine (Xa-1) of the purity content (HPLC) 99.3% in the form of colorless crystals, Mp. 97-98 ° C.

¹H-NMR-Daten (400 MHz., Solvens: CD₃CN, interner Standard: Tetramethylsilan δ = 0.00 ppm; s = Singulett, br. s = breites Singulett, d = Dublett, dd = Doppeldublett, m = Multiplett, q = Quartett, t = Triplett)
Xa-6: δ = 0.96 (t, 3H); 1.6-1.8 (m, 2H); 3.02 (dd, 1H); 3.41 (dd, 1H); 4.45 (s, 2H); 4.62 (m, 1H); 7.14 (dd, 1H); 7.15-7.33 (m, 3H); 7.40-7.48 (m, 2H); 7.65 (dd, 1H); 8.45 (dd, 1H) ppm

Analog can be produced:

¹ H-NMR data (400 MHz., Solvent: CD ₃ CN, internal standard: tetramethylsilane δ = 0.00 ppm; s = singlet, br. S = broad singlet, d = doublet, dd = double doublet, m = multiplet, q = Quartet, t = triplet)
Xa-6: δ = 0.96 (t, 3H); 1.6-1.8 (m, 2H); 3.02 (dd, 1H); 3.41 (dd, 1H); 4.45 (s, 2H); 4.62 (m, 1H); 7.14 (dd, 1H); 7.15-7.33 (m, 3H); 7.40-7.48 (m, 2H); 7.65 (dd, 1H); 8.45 (dd, 1H) ppm

4. 2-chloro-3- (4,5-dihydroisoxazol-3-yl) pyridine (XIa-1)

22.5 g (0.14 mol) of 2-chloronicotinaldehyde oxime are placed in a pressure vessel dissolved in 1650 ml of methylene chloride. The autoclave is closed and rendered inert with nitrogen. Ethylene is pressed on, reached to 5 bar. With good stirring 279 g (231.3 ml) sodium hypochlorite solution (10-13%) in the course of 1 hour at 20 ° C pumped. After dosing is stirred for 15 hours at room temperature. To Relaxing the pressure vessel becomes excess Ethylene blown out with nitrogen. The organic phase is separated off, washed with water and dried with Baylith TE 144. After removal of the solvent in vacuo gives 23.8 g 2-chloro-3- (4,5-dihydroisoxazol-3-yl) pyridine (XIa-1) of the purity content (HPLC) 98.1%, logp = 0.97.

¹H-NMR-Daten (400 MHz., Solvens: CD₃CN, interner Standard: Tetramethylsilan δ = 0.00 ppm; s = Singulett, br. s = breites Singulett, d = Dublett, dd = Doppeldublett, m = Multiplett, q = Quartett, t = Triplett)
XIa-2: δ = 1.38 (d, 3H); 3.07 (dd, 1H); 3.54 (dd, 1H); 4.88 (m, 1H); 7.38 (dd, 1H); 7.96 (dd, 1H); 8.40 (dd, 1H) ppm
XIa-3: δ = 0.95 (d, 3H); 0.99 (d. 3H); 3.19 (dd, 1H); 3.44 (dd, 1H); 4.52 (m, 1H); 7.38 (dd, 1H); 7.94 (dd, 1H); 8.40 (dd, 1H) ppm

1H-NMR-Daten (400 MHz., Solvens: CD₃CN, interner Standard: Tetramethylsilan δ = 0.00 ppm; s = Singulett, br. s = breites Singulett, d = Dublett, dd = Doppeldublett, m = Multiplett, q = Quartett, t = Triplett)
XId-1: δ = 3.47 (t, 2H); 4.40 (t, 2H); 7.39-7.44 (m, 1H); 7.58-7.63 (m, 1H); 8.46 (m, 1H) ppmAnalog can be produced:

¹ H-NMR data (400 MHz., Solvent: CD ₃ CN, internal standard: tetramethylsilane δ = 0.00 ppm; s = singlet, br. S = broad singlet, d = doublet, dd = double doublet, m = multiplet, q = Quartet, t = triplet)
XIa-2: δ = 1.38 (d, 3H); 3.07 (dd, 1H); 3.54 (dd, 1H); 4.88 (m, 1H); 7.38 (dd, 1H); 7.96 (dd, 1H); 8.40 (dd, 1H) ppm
XIa-3: δ = 0.95 (d, 3H); 0.99 (i.e., 3H); 3.19 (dd, 1H); 3.44 (dd, 1H); 4.52 (m, 1H); 7.38 (dd, 1H); 7.94 (dd, 1H); 8.40 (dd, 1H) ppm

1H NMR data (400 MHz, solvent: CD ₃ CN, internal standard: tetramethylsilane δ = 0.00 ppm, s = singlet, br s = broad singlet, d = doublet, dd = double doublet, m = multiplet, q = Quartet, t = triplet)
XId-1: δ = 3.47 (t, 2H); 4.40 (t, 2H); 7.39-7.44 (m, 1H); 7.58-7.63 (m, 1H); 8.46 (m, 1H) ppm

B. Formulation Examples

• a) a dust is obtained by adding 10 parts by weight of a compound of formula (I) and 90 parts by weight Mixed talc as an inert material and crushed in a hammer mill.
• b) A wettable powder readily dispersible in water is obtained by adding 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight lignosulfonic acid potassium and 1 part by weight of oleoylmethyltaurine acid Sodium as wetting and dispersing mixes and in a pin mill served basis.
• c) A readily water-dispersible dispersion concentrate is obtained by mixing 20 weight parts by weight of a compound of formula (I) with 6 parts by weight of alkylphenol polyglycol ether ^(® Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71st Parts of paraffinic mineral oil (boiling range, for example, about 255 to about 277 ° C) and milled in a ball mill to a fineness of less than 5 microns.
• d) An emulsifiable concentrate is obtained from 15 parts by weight a compound of formula (I), 75 parts by weight of cyclohexanone as Solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.
• e) A water-dispersible granules are obtained by you

75 parts by weight one Compound of the formula (I) 10 parts by weight ligninsulfonate calcium, 5 parts by weight sodium lauryl sulfate, 3 parts by weight polyvinyl alcohol and 7 parts by weight kaolin

• mixes, on a pin mill milled and the powder in a fluidized bed by spraying granulated by water as granulating liquid.
• f) A water-dispersible granule is also obtained by

25 parts by weight one Compound of the formula (I) 5 parts by weight 2,2'-dinaphthylmethane-6,6'-disulfonate Sodium, 2 parts by weight oleoylmethyltaurinate Sodium, 1 part by weight polyvinyl alcohol, 17 parts by weight calcium carbonate and 50 parts by weight water

• on a colloid mill homogenized and pre-shredded, then on a Milled bead mill and the suspension thus obtained in a Spray tower atomized by means of a one-fluid nozzle and dry.

C. Biological examples

1. Herbicidal action or crop plant compatibility in the pre-emergence

seed of mono- or dicotyledonous weeds or crop plants are in Wood fiber pots in sandy loam and designed with Covered earth. Formulated in the form of wettable powders (WP) Compounds of the invention are then considered aqueous suspension or emulsion with an amount of water used of the equivalent of 600 l / ha with the addition of 0.2% wetting agent on the Surface of the cover soil applied.

To The pots are treated in the greenhouse placed and under good growth conditions for the Test plants kept. After about 3 weeks, the effect of the preparations scored visually compared to untreated controls (herbicides Effect in percent (%): 100% effect = plants have died, 0% effect = like control plants).

As show the results have inventive Compounds a good herbicidal pre-emergence activity against broad spectrum of grass weeds and weeds on. The compounds of the invention have For example, a very good herbicidal activity against harmful plants such as Alopecurus myosuroides, Matricaria inodora and Stellaria media pre-emergence at an application rate of 0.08 kg and less active substance per hectare.

The following results were achieved with the compounds according to the invention in pre-emergence: connection dosage unit ALOMY MATIN STEMS Ia-1 80 g / ha 90 90 90 Ia-2 80 g / ha 90 90 90 Ia-3 80 g / ha 80 80 80 Ia-4 80 g / ha 80 90 90 Ia-9 80 g / ha 80 Ia-10 80 g / ha 80 80 80 Ia-11 80 g / ha 90 80 80 Ia-13 80 g / ha 90 80 80 Ia-15 80 g / ha 80 80 Ia-16 80 g / ha 80 80 Ia-17 80 g / ha 90 Ia-19 80 g / ha 80 80 Ia-20 80 g / ha 80 Ia-21 80 g / ha 80 80 Ia-22 80 g / ha 100 Ia-23 80 g / ha 80 Ia-24 80 g / ha 90 90 90

• ALOMY: Acker-Fuchsschwanz(gras) (Alopecurus myosuroides)
• MATIN: Geruchlose Kamille (Matricaria inodora)
• STEME: Vogelmiere (Stellaria media)

In the table, the individual cultures have the following abbreviations:

• ALOMY: field foxtail (gras) (Alopecurus myosuroides)
• MATIN: Odorless chamomile (Matricaria inodora)
• STEME: Chickweed (Stellaria media)

2. Post-emergence herbicidal action

seed of mono- or dicotyledonous weeds or crop plants are in Wood fiber pots laid out in sandy clay soil, with soil covered and in the greenhouse under good growth conditions dressed. 2 to 3 weeks after sowing, the test plants treated at the single leaf stage. The in the form of wettable powders (WP) formulated compounds of the invention are then used as aqueous suspension or emulsion with an amount of water equivalent to 600 l / ha with addition of 0.2% wetting agent sprayed onto the green parts of the plant. After about 3 weeks life of the test plants in the greenhouse under optimal growth conditions, the effect of the preparations scored visually compared to untreated controls (herbicides Effect in percent (%): 100% effect = plants have died, 0% effect = like control plants).

As show the results have inventive Compounds a good herbicidal postemergence against a broad spectrum of grass weeds and weeds on. For example, the inventive Compounds a very good herbicidal activity against harmful plants such as Alopecurus myosuroides, Echinochloa crus-galli, Lolium multiflorum, Abutilon theophrasti, Amaranthus retroflexus, Pharitis purpurea, Stellaria media and Viola tricolor postemergence at an application rate of 0.08 kg and less active substance per Hectares.

The following results were achieved with the compounds according to the invention in postemergence:

• ALOMY: Acker-Fuchsschwanz (Alopecurus myosuroides.)
• ECHCG: Hühnerhirse (Echinochloa crus-galli)
• LOLMU: Vielblütiger Lolch (Lolium multiflorum)
• ABUTH: Samtpappel (Abutilon theophrasti)
• AMARE: Zurückgekrümmter Fuchsschwanz (Amaranthus retroflexus)
• PHBPU: Purpur-Prachtwinde (Pharbitis/Ipomoea purpurea)
• STEME: Vogelmiere (Stellaria media)
• VIOTR: Wildes Stiefmütterchen (Viola tricolor)

In the table, the individual cultures have the following abbreviations:

• ALOMY: Field Foxtail (Alopecurus myosuroides.)
• ECHCG: Barnyardgrass (Echinochloa crus-galli)
• LOLMU: Many-flowered Lolch (Lolium multiflorum)
• ABUTH: Velvet Poplar (Abutilon theophrasti)
• AMARE: Curved Foxtail (Amaranthus retroflexus)
• PHBPU: Purple Glory (Pharbitis / Ipomoea purpurea)
• STEME: Chickweed (Stellaria media)
• VIOTR: Wild Pansy (Viola tricolor)

QUOTES INCLUDE IN THE DESCRIPTION

This list The documents listed by the applicant have been automated generated and is solely for better information recorded by the reader. The list is not part of the German Patent or utility model application. The DPMA takes over no liability for any errors or omissions.

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Claims (17)

N-azinyl-N'-pyridylsulfonylureas of the general formula (I)

in which V, W, X and Y are chosen such that one of these indices is nitrogen and the remaining indices are carbon atoms which may be unsubstituted or substituted by the represented group R ⁸ ; A is selected from the group consisting of nitrogen and CR ⁹ ; wherein R ^{9 is} selected from the group consisting of hydrogen, alkyl, halo and haloalkyl; R ^{1 is} selected from the group consisting of hydrogen and an optionally substituted radical selected from alkyl, alkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aralkyl and aryl; R ^{2 is} selected from the group consisting of hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy, optionally substituted by halogen alkylthio, optionally substituted by halogen alkylamino or optionally substituted by halogen dialkylamino: R ^{3 is} selected from A group consisting of hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy, optionally substituted by halogen alkylthio, optionally substituted by halogen alkylamino or optionally substituted by halogen dialkylamino; R ⁴ to R ⁷ , each independently, are selected from the group consisting of hydrogen, halogen, cyano, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, the radicals being unsubstituted or one or more radicals selected from the group consisting of halogen, cyano, alkoxy or alkylthio, or R ⁴ and R ⁶ or R ⁵ and R ^{7 represent} an optionally interrupted by oxygen or sulfur alkylidene group; R ^{8 is} selected from the group consisting of hydrogen, halogen, cyano, thiocyanato, nitro, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, or dialkylaminocarbonyl, where the radicals may be unsubstituted or one or more radicals selected from the group consisting of halogen, cyano, alkoxy and alkylthio, can carry; Q is selected from the group consisting of oxygen, or sulfur and salts of compounds of formula (I). N-Azinyl-N'-pyridylsulfonylureas according to claim 1, characterized in that the substituent A is selected is from the group consisting of nitrogen and CH. N-azinyl-N'-pyridysulfonylureas according to claim 1 or 2, characterized in that the substituent R ^{1 is} selected from the group consisting of hydrogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy, optionally substituted by halogen Alkoxyalkyl, optionally substituted by halogen alkenyl and optionally substituted by halogen alkynyl. N-azinyl-N'-pyridylsulfonylureas according to any one of claims 1 to 3, characterized in that the substituent R ^{2 is} selected from the group consisting of hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy, optionally substituted by halogen alkylthio, optionally substituted by halogen alkylamino and optionally substituted by halogen dialkylamino. N-azinyl-N'-pyridysulfonylureas according to any one of claims 1 to 5, characterized in that the substituent R ^{3 is} selected from the group consisting of hydrogen, halogen, optionally Halogen-substituted alkyl, optionally halogen-substituted alkoxy, optionally halogen-substituted alkylthio, optionally halogen-substituted alkylamino and optionally halogen-substituted dialkylamino. N-azinyl-N'-pyridysulfonylureas according to any one of claims 1 to 5, characterized in that the substituents R ⁴ to R ⁷ , in each case independently of one another, are selected from the group consisting of hydrogen, halogen, cyano, thiocyanato, optionally substituted by halogen, alkoxy optionally substituted by halogen, optionally substituted by halogen alkylthio, optionally substituted by halogen alkylsulfinyl, optionally substituted by halogen alkylsulfonyl, optionally substituted by halogen alkylamino, optionally substituted by halogen alkylcarbonyl, optionally substituted by halogen alkoxycarbonyl or optionally by Halogen substituted alkylaminocarbonyl. N-azinyl-N'-pyridysulfonylureas according to any one of claims 1 to 6, characterized in that the substituent R ^{8 is} selected from the group consisting of hydrogen, halogen, cyano, thiocyanato, optionally halogen-substituted alkyl, optionally Halogen-substituted alkoxy, optionally substituted by halogen alkylthio, optionally substituted by halogen alkylsulfinyl, optionally substituted by halogen alkylsulfonyl, optionally substituted by halogen alkylamino, optionally substituted by halogen alkylcarbonyl, optionally substituted by halogen alkoxycarbonyl and optionally substituted by halogen alkylaminocarbonyl. A process for the preparation of N-azinyl-N'-pyridylsulfonylureas according to any one of claims 1 to 7, characterized by one of the following process steps: (a) reaction of (4,5-dihydroisoxazol-3-yl) pyridine-sulfonamides of the general Formula (II)

with a heterocyclic (thio) carbamate of the general formula (III)

wherein R ^{12 is} a substituted or unsubstituted (C ₁ -C ₂₀ ) -hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (C ₁ -C ₄ ) -alkyl and wherein V, W, X, Y, R ¹ to R ⁸ , Q and A have the meaning of any one of claims 1 to 7; or (b) reaction of (4,5-dihydroisoxazol-3-yl) pyridine-sulfonic acid iso (thio) cyanates of the general formula (IV)

with an aminoheterocycle of the general formula (V)

wherein V, W, X, Y, R ¹ to R ⁸ , Q and A have the meaning of any one of claims 1 to 7; or (c) reaction of (4,5-dihydroisoxazol-3-yl) pyridine-sulfonyl (thio) carbamates of the general formula (VI)

in which R ¹² denotes a substituted or unsubstituted (C ₁ -C ₂₀ ) -hydrocarbon radical such as aryl or alkyl, preferably optionally substituted phenyl or optionally substituted (C ₁ -C ₄ ) -alkyl, with an aminoheterocycle of the general formula (V)

wherein V, W, X, Y, R ¹ to R ⁸ , Q and A are as defined in any one of claims 1 to 7; or (d) reaction of (4,5-dihydroisoxazol-3-yl) pyridine-sulfonamides of the general formula (II)

with an iso (thio) cyanate of the general formula (VII)

optionally in the presence of a reaction auxiliary, wherein R ^{1 is} hydrogen and V, W, X, Y, R ² to R ⁸ , Q and A have the meaning of any one of claims 1 to 7; or (e) reaction of an aminoheterocycle of the general formula (V)

initially base-catalyzed with a carbonic acid ester and the intermediate formed of the general formula (III)

in a one-pot reaction with a (4,5-dihydroisoxazol-3-yl) pyridine-sulfonamide of the general formula (II)

wherein V, W, X, Y, R ¹ to R ⁸ , Q and A are as defined in any one of claims 1 to 7; or (f) reaction of (4,5-dihydroisxazol-3-yl) pyridine-sulfonic acid halides of the general formula (VIII)

wherein Hal is a halogen atom with a (thio) cyanate to an iso (thio) cyanate of the general formula (IV)

or a solvated (stabilized) derivative, and then with an amino heterocycle of general formula (V)

wherein V, W, X, Y, R ¹ to R ⁸ , Q and A are as defined in any one of claims 1 to 7; or (g) reacting (4,5-dihydroisoxazol-3-yl) pyridine-sulfonic acid amides of the general formula (II) with a heterocyclic bis-carbamate of the general formula (IX)

wherein R ^{12 is} a substituted or unsubstituted (C ₁ -C ₂₀ ) hydrocarbon radical, in the presence of a basic reaction auxiliary, wherein Q is oxygen and V, W, X, Y, R ¹ to R ⁸ , and A is as defined in any of Claims 1 to 7; or (h) reaction of (4,5-dihydroisoxazol-3-yl) pyridine-sulfonic acid amides of the general formula (II)

base catalysis with a carbonic acid ester and reaction of the intermediate formed of the general formula (VI)

in a one-pot reaction with an aminoheterocycle of the general formula (V)

wherein V, W, X, Y, R ¹ to R ⁸ , Q and A have the meaning according to one of claims 1 to 7. Compounds of the general formula (II)

in which the radicals V, W, X, Y, R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 have} the meanings according to one of claims 1 to 7. Compounds of the general formula (VIII)

in which the radicals V, W, X, Y, R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and Hal have the meanings according to one of claims 1 to 7. Compounds of the general formula (XI)

in which the radicals V, W, X, Y, R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and Hal have the meanings according to one of claims 1 to 7. Compounds of the general formula (X)

in which the radicals V, W, X, Y, R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 have} the meanings according to one of claims 1 to 7. Compositions containing at least one compound of the general formula (I) according to one of the claims 1 to 7. Composition according to Claim 13, characterized that the composition comprises at least one further active substance, which is selected from the group consisting of at least another herbicide and at least one safener. Use of the compounds of the general formula (I) according to any one of claims 1 to 7 as herbicides and plant growth regulators. Use of the compositions according to one Claim 14 or 15 as herbicides and plant growth regulators. Use according to claim 15 or 16 for plant control in special crops or as a plant protection regulator.