JPWO2021191035A5 - - Google Patents

Description

The present invention relates to dioxazoline compounds and compositions containing the same. The invention also relates to the use of dioxazoline compounds or corresponding compositions for controlling unwanted vegetation. Furthermore, the invention relates to a method of applying a dioxazoline compound or a corresponding composition.

There is a need for new herbicides that are substantially non-toxic to humans and animals and have high activity and selectivity, especially for the purpose of controlling unwanted vegetation, especially in crops.

WO12130798, WO1404882, WO14048882, WO18228985, WO18228986, WO19034602 and WO19145245 describe 3-phenylisoxazoline-5-carboxamides and their use as herbicides.

Prior art compounds often have insufficient herbicidal activity, especially at low application rates, and/or poor compatibility with crop plants due to insufficient selectivity.

It is therefore an object of the present invention to provide further compounds which have a strong herbicidal activity, in particular even at low application rates, a sufficiently low toxicity to humans and animals, and/or a high compatibility with crop plants. . Dioxazoline compounds should also exhibit a broad spectrum of activity against a large number of different unwanted plants.

These and further objectives are achieved by the compounds of formula (I) defined below, including their agriculturally acceptable salts, amides, esters or thioesters.

Therefore, the present invention provides formula (I)

[wherein the substituents have the following meanings:
R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-Haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, ( C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkoxy;
R ² is hydrogen, halogen, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )- is haloalkoxy;
R ³ is hydrogen, halogen, nitro, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, hydroxy-(C ₁ -C ₃ )-alkyl, (C ₃ - _C5 )-cycloalkyl, ( _C3 - _C5 )-halocycloalkyl, hydroxy-( _C3 - _C5 )-cycloalkyl, (C1 _{- C3} )-alkoxy, ( _C1 - _C3 )- Haloalkoxy, (C ₁ -C ₃ )-alkoxycarbonyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl;
^R4 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C4 )-halocycloalkyl, ( _C1 - _C3) )-alkoxy, (C ₁ -C ₃ )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkylthio;
R ⁵ is hydrogen, halogen, nitro, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, hydroxy-(C ₁ -C ₃ )-alkyl, (C ₃ - _C5 )-cycloalkyl, ( _C3 - _C5 )-halocycloalkyl, hydroxy-( _C3 - _C5 )-cycloalkyl, (C1 _{- C3} )-alkoxy, ( _C1 - _C3 )- Haloalkoxy, (C ₁ -C ₃ )-alkoxycarbonyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl;
R ⁶ is hydrogen, halogen, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )- is haloalkoxy;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond (X ⁰ ), or (X ¹ ), (X ² ), (X ³ ), (X ⁴ ), (X ⁵ ) and (X ⁶ ):

is a divalent unit from the group consisting of;
R ⁸ to R ¹³ are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO ₂ R ^e , CONR ^b R ^d , NR ^b CO ₂ R ^e , R ^a , or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₅ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl (respectively, fluorine, chlorine, bromine, iodine, hydroxyl and cyano), or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-alkenyloxy , (C ₃ -C ₆ )-alkynyloxy, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl (respectively, fluorine, chlorine , bromine, iodine, cyano and (C ₁ -C ₂ )-alkoxy);
Y is hydrogen, cyano, hydroxyl, Z,
or
(C ₁ -C ₁₂ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₁₂ )-alkenyl or (C ₂ -C ₁₂ )-alkynyl, each of which represents fluorine, chlorine, Bromine, iodine, cyano, hydroxyl, OR ^d , Z, OZ, NHZ, S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , CO ₂ R ^e , CONR ^b R ^h , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e , NR ^b SO ₂ NR ^b R ^e , OCONR substituted by m groups from the group consisting of ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e ;
Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and CO ₂ R ^e , CONR ^b R ^h , S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e NR ^b SO ₂ NR ^b R ^e , OCONR ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e , R ^b , R ^c , R ^e and R ^f a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring (other than phenyl) substituted by m groups from the group in which the sulfur and carbon atoms are has n oxo groups;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which represents fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C ₁ -C 6 )-cycloalkyl. substituted by m groups selected from the group consisting of ₃ )-alkoxy;
R ^b is hydrogen, (C ₁ -C ₃ )-alkoxy, or R ^a ;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^d is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₃ -C ₆ )-cycloalkyl-( C ₁ -C ₃ )-alkyl, phenyl-(C ₁ -C ₃ )-alkyl, furanyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which contains fluorine, Chlorine, bromine, cyano, CO ₂ R ^a , CONR ^b R ^h , (C ₁ -C ₂ )-alkoxy, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl, phenylthio, phenylsulfinyl and phenylsulfonyl);
R ^e is R ^d ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₂ )-alkoxy, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-Alkoxycarbonyl-(C ₁ -C ₆ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which represents fluorine, chlorine, bromine, cyano, CO ₂ R ^a and (C ₁ substituted by m groups selected from the group consisting of -C ₂ )-alkoxy);
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1 or 2;
r is 1, 2, 3, 4, 5 or 6]
5 -methyl-3-phenyl - 1,4, Compounds of formula (I) are provided, excluding 2-dioxazole-5-carboxamide.

The invention also relates to formulations comprising at least one compound of formula (I) and auxiliaries customary for the formulation of crop protection agents.

The invention also provides at least one compound of formula (I) (component A) and at least one further compound selected from herbicidal compound B (component B) and safener C (component C). Provides a combination, including.

The invention also provides the use of compounds of formula (I) as herbicides, ie for controlling undesirable vegetation.

The present invention further provides a method for controlling undesirable vegetation, comprising applying a herbicidally effective amount of at least one compound of formula (I) to plants, their seeds and/or their habitat. provide.

According to the invention, if the compound of formula (I), the herbicidal compound B and/or the safener C described herein are capable of forming geometric isomers (e.g. E/Z isomers), It is possible to use both pure isomers and mixtures thereof.

If the compound of formula (I), herbicidal compound B and/or safener C as described herein has one or more chiral centers and therefore exists as enantiomers or diastereomers, According to the invention it is possible to use both the pure enantiomers and diastereomers as well as mixtures thereof.

When the compound of formula (I), the herbicidal compound B and/or the safener C described herein have an ionizable functional group, they may be present in the form of their agriculturally acceptable salts. It can also be used in Suitable are generally salts of cations and acid addition salts of acids whose cations and anions, respectively, do not adversely affect the activity of the active compound.

Preferred cations are ions of alkali metals (preferably lithium, sodium and potassium ions), alkaline earth metal ions (preferably calcium and magnesium ions), and transition metal ions (preferably manganese, copper, zinc and iron ion), further ammonium, and 1 to 4 hydrogen atoms are C ₁ -C ₄ -alkyl, hydroxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl , hydroxy-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, phenyl or benzyl substituted ammonium (preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethyl Ammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2- Hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)-ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium ( trolamine salts), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salts)), as well as phosphonium ions, sulfonium ions, preferably tris (C ₁ -C ₄ -alkyl)sulfonium (e.g. trimethylsulfonium), and sulfoxonium ions, preferably tri(C ₁ -C ₄ -alkyl)sulfoxonium, and finally polybasic amines (e.g. N,N-bis -(3-aminopropyl)methylamine and diethylenetriamine).

The anions of useful acid addition salts are mainly chloride ion, bromide ion, fluoride ion, iodine ion, hydrogen sulfate ion, methyl sulfate ion, sulfate ion, dihydrogen phosphate ion, hydrogen phosphate ion, nitrate ion, and bicarbonate. ion, carbonate ion, hexafluorosilicate ion, hexafluorophosphate ion, benzoate ion, and also anions of C ₁ -C ₄ -alkanoic acids, preferably formate, acetate, propionate and butyrate. .

The compounds of formula (I), herbicidal compounds B and/or safeners C having carboxyl groups as described herein can be used in the form of acids, agriculturally suitable salts as above, or otherwise agriculturally acceptable derivatives, for example as amides (for example as mono- and di-C ₁ -C ₆ -alkylamides or arylamides), as esters (for example as allyl esters, propargyl esters, C ₁ -C ₁₀ -alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters), and also as thioesters (for example as C ₁ -C ₁₀ -alkylthioesters). Preferred mono- and di-C ₁ -C ₆ -alkylamides are methyl and dimethyl amides. Preferred arylamides are, for example, anilides and 2-chloroanilides. Preferred alkyl esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred _C1 - _C4 -alkoxy- _C1 - _C4 -alkyl esters are linear or branched _C1 - _C4 -alkoxyethyl esters, such as 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl esters. An example of a linear or branched _C1 - _C10 -alkylthioester is the ethylthioester.

The terms used for organic groups in the definition of the variables are, for example, the expression "halogen", which is a generic term denoting the individual members of these groups of organic units.

The prefix C _x -C _y indicates the possible number of carbon atoms in a particular case. All hydrocarbon chains may be straight or branched.
Halogen: fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine;
Alkyl and complex groups, such as alkoxy, alkylamino, alkyl moieties of alkoxycarbonyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 10 carbon atoms, such as C ₁ -C ₁₀ -alkyl, For example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- Dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl , 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2- Trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; heptyl, octyl, 2-ethylhexyl and their positional isomers; nonyl, decyl and their Positional isomers;
Haloalkyl: A straight-chain or branched alkyl group (as defined above) having 1 to 10 carbon atoms, in which some or all of the hydrogen atoms in these groups are replaced by halogen atoms, as defined above. In one embodiment, the alkyl group is substituted at least once or completely by specific halogen atoms, preferably fluorine, chlorine or bromine. In a further embodiment, the alkyl group is partially or fully halogenated with different halogen atoms, in the case of mixed halogen substitution a combination of chlorine and fluorine is preferred. Particularly preferred is ( _C1 - _C3 )-haloalkyl, more preferably ( _C1 - _C2 )-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2- Chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoro is prop-2-yl;
Alkenyl, and also the alkenyl moiety in complex groups, such as alkenyloxy: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and one double bond in any position. According to the invention, it may be preferred to _use small alkenyl groups, e.g. (C ₂ -C ₄ )-alkenyl, on the other hand, _larger alkenyl groups, e.g. It may be preferable to use Examples of alkenyl groups are, for example, _C2 - _C6 -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1- Propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-Methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2- Methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1- Propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl- 1-Pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3- Pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2, 3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1- Ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
Haloalkenyl: an alkenyl group as defined above partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g. 2-chloroprop-2-en-1-yl, 3-chloroprop-2-en-1 -yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2-en-1-yl, 2 ,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1 -yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1-yl or 2,3-dibromobut-2-en-1-yl;
Alkynyl and the alkynyl moiety in composite groups, e.g. alkynyloxy: straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and one or two triple bonds in any position, e.g. C ₂ - C ₆ -alkynyl, for example ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4 -pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2 -Propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl -3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl -2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2 -butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
Haloalkynyl: an alkynyl group as defined above partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g. 1,1-difluoroprop-2-yn-1-yl, 3-chloroprop-2- Yn-1-yl, 3-bromoprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yl -1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4 -yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;
Cycloalkyl, and also the cycloalkyl moiety in composite radicals: monocyclic or bicyclic saturated hydrocarbon radicals having 3 to 10, especially 3 to 6 carbon ring members, for example C ₃ -C ₆ -cyclo Alkyl, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. Examples of bicyclic groups include bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. In this context, optionally substituted C ₃ -C ₈ -cycloalkyl means a cycloalkyl group having 3 to 8 carbon atoms and at least one hydrogen atom, for example 1, 2 , 3, 4 or 5 hydrogen atoms are replaced by substituents which are inert under the conditions of the reaction. Examples of inert substituents are CN, _C1 - _C6 -alkyl, _C1 - _C4 -haloalkyl, _C1 - _C6 -alkoxy, _C3 - _C6 -cycloalkyl and _C1 - _C4- is alkoxy-C ₁ -C ₆ -alkyl;
Halocycloalkyl and the halocycloalkyl moiety in halocycloalkoxy, halocycloalkylcarbonyl, etc.: some or all of the hydrogen atoms may be replaced by the above-mentioned halogen atoms, in particular fluorine, chlorine and bromine, 3 to 10 a monocyclic saturated hydrocarbon group having carbon ring members (as defined above);
Cycloalkoxy: a cycloalkyl group as defined above linked through an oxygen;
Alkoxy, and also the alkoxy moiety in a composite group, such as alkoxyalkyl: an alkyl group as defined above, linked via an oxygen and preferably having 1 to 10, more preferably 2 to 6 carbon atoms . Examples are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, and also for example pentoxy, 1-methylbutoxy, 2 -Methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3 -Methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3- Dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
Haloalkoxy: Alkoxy as defined above, in which some or all of the hydrogen atoms in these groups have been replaced by halogen atoms as defined above under haloalkyl, in particular by fluorine, chlorine or bromine. . Examples are _OCH2F , _{OCHF2 ,} OCF3, OCH2Cl, _OCHCl2 , _OCCl3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2 _- fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2- Fluoroethoxy, 2,2,2-trichloroethoxy, OC ₂ F ₅ , 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy , 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH ₂ -C ₂ F ₅ , OCF ₂ -C ₂ F ₅ , 1-(CH ₂ F)-2-fluoroethoxy, 1-(CH ₂ Cl)-2-chloroethoxy, 1-(CH ₂ Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chloro butoxy, 4-bromobutoxy or nonafluorobutoxy; and also 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6 - is chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
Alkylthio: an alkyl group as defined above, which is attached via a sulfur atom and preferably has 1 to 6, more preferably 1 to 3 carbon atoms.
Alkylsulfinyl: an alkyl group as defined above, linked via S(O), preferably having 1 to 6, more preferably 1 to 3 carbon atoms.
Alkylsulfonyl: an alkyl group as defined above, linked via S(O) ₂ and preferably having 1 to 6, more preferably 1 to 3 carbon atoms.
Hydroxyl: OH group attached through an O atom;
Cyano: CN group bonded through a C atom;
Nitro: NO ₂ group linked through an N atom.

The preferred embodiments of the invention mentioned herein below are to be understood as preferred independently of each other or in combination with each other.

According to a particular embodiment of the invention, preference is given to compounds of formula (I) in which the variables, independently of each other or in combination with each other, have the following meanings:

Preferred compounds according to the invention are those in which R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C _{3 )} - )-alkenyl, (C ₂ -C ₃ )-alkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-alkoxy , is a compound of formula (I).

More preferred compounds according to the invention are those in which R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl and (C ₁ -C ₃ )-alkoxy-(C ₁ -C A compound of formula (I) selected from the group consisting of ₃ )-alkyl.

Similarly, preferred compounds according to the invention are compounds of formula (I), in which R ¹ is selected from the group consisting of hydrogen, methyl and methoxymethyl.

In particular, R ¹ is hydrogen.

Further preferred compounds according to the invention are those of formula (I), in which R ² is selected from the group consisting of hydrogen, halogen and (C ₁ -C ₃ )-alkyl.

Similarly, preferred compounds according to the invention are compounds of formula (I) in which R ² is selected from the group consisting of hydrogen, fluorine, chlorine and methyl.

In particular, ^R2 is hydrogen.

Further preferred compounds according to the invention are those in which R ³ is hydrogen, halogen, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl and (C ₁ -C ₃ )-halo A compound of formula (I) selected from the group consisting of alkoxy.

More preferred compounds according to the invention are those of formula (I), in which R ³ is selected from the group consisting of halogen, cyano and (C ₁ -C ₃ )-alkyl.

Similarly, preferred compounds according to the invention are those of formula (I) in which R ³ is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, methyl, trifluoromethyl and trifluoromethoxy.

In particular R ³ is hydrogen or halogen, very especially chlorine or fluorine.

Further preferred compounds according to the invention are compounds of formula (I), wherein R ⁴ is selected from the group consisting of hydrogen and halogen.

Similarly, preferred compounds according to the invention are those of formula (I), in which R ⁴ is selected from the group consisting of hydrogen, fluorine, chlorine and bromine.

In particular R ⁴ is hydrogen or hydrogen, fluorine or chlorine, very especially hydrogen.

Further preferred compounds according to the invention are those in which R ⁵ is hydrogen, halogen, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl and (C ₁ -C ₃ )-halo A compound of formula (I) selected from the group consisting of alkoxy.

More preferred compounds according to the invention are those of formula (I), wherein R ⁵ is selected from the group consisting of halogen, cyano and (C ₁ -C ₃ )-alkyl.

Similarly, preferred compounds according to the invention are those of formula (I) in which R ⁵ is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, methyl, trifluoromethyl and trifluoromethoxy.

In particular R ⁵ is hydrogen or halogen, very especially chlorine or fluorine.

Further preferred compounds according to the invention are wherein R ³ and R ⁵ are selected from the group consisting of hydrogen, halogen, hydroxyl, cyano and (C ₁ -C ₃ )-alkyl, and at least one of R ³ and R ⁵ is hydrogen. is not a compound of formula (I).

Further preferred compounds according to the invention are compounds of formula (I), in which R ⁶ is selected from the group consisting of hydrogen, halogen and (C ₁ -C ₃ )-alkyl.

Similarly, preferred compounds according to the invention are those of formula (I), in which R ⁶ is selected from the group consisting of hydrogen, fluorine, chlorine and methyl.

In particular, R ⁶ is hydrogen.

Further preferred compounds according to the invention are in which R ⁷ is (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl, (C ₂ -C ₃ )-alkenyl, and (C ₁ -C _{3 )} -alkenyl. )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine , and (C ₁ -C ₂ )-alkoxy; be. In this connection, m is preferably 0, 1, 2 or 3.

Similarly, preferred compounds according to the invention are those in which R ⁷ is (C ₁ -C ₂ )-alkyl, cyclopropyl, (C ₁ -C ₂ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, and (C 2 -C 3 )-alkenyl. A compound of formula (I) selected from the group consisting of ₁ -C ₂ )-alkoxy.

In particular R ⁷ is methyl, chloromethyl, trifluoromethyl, cyclopropyl, ethenyl and methoxy, very especially methyl.

In the compound of formula (I), X is a bond (X ⁰ ) or a group consisting of (X ¹ ), (X ² ), (X ³ ), (X ⁴ ), (X ⁵ ) and (X ⁶ ) The intramolecular (X ¹ ), (X ² ), (X ³ ), (X ⁴ ), (X ⁵ ) and (X ⁶ ) orientations are selected from the group consisting of divalent units from The arrow on the left represents the bond to the adjacent nitrogen, and the arrow on the right represents the bond to the adjacent group Y.

In a preferred embodiment (compounds of formula (IX ⁰ )), X is a bond (X ⁰ ):

In another preferred embodiment (compounds of formula (IX ¹ )), X is (X ¹ ) and the orientation of (X ¹ ) within the molecule is as shown, with the left arrow pointing to the adjacent The arrow on the right represents the bond to the adjacent group Y:

In another preferred embodiment (compounds of formula (IX ² )), X is (X ² ) and the orientation of (X ² ) within the molecule is as shown, with the left arrow indicating The arrow on the right represents the bond to the adjacent group Y:

In another preferred embodiment (compounds of formula (IX ³ )), X is (X ³ ) and the orientation of (X ³ ) within the molecule is as shown, with the left arrow pointing to the adjacent The arrow on the right represents the bond to the adjacent group Y:

In another preferred embodiment (compounds of formula (IX ⁴ )), X is (X ⁴ ) and the orientation of (X ⁴ ) within the molecule is as shown, with the left arrow pointing to the adjacent The arrow on the right represents the bond to the adjacent group Y:

In another preferred embodiment (compound of formula (IX ⁵ )), X is (X ⁵ ) and the orientation of (X ⁵ ) in the molecule is as shown, with the left arrow representing the bond to the adjacent nitrogen and the right arrow representing the bond to the adjacent group Y:

In another preferred embodiment (compounds of formula (IX ⁶ )), X is (X ⁶ ), and the orientation of (X ⁶ ) within the molecule is as shown, with the left arrow pointing to the adjacent The arrow on the right represents the bond to the adjacent group Y:

_{Further preferred compounds according to the invention are} ^wherein _{​ ​ 2} , C(CH ₃ ) ₂ , C(CH ₃ ) ₂ CH ₂ , C(iPr)CH ₃ , CH(CH ₂ iPr)CH ₂ , CH ₂ CH=CH, C(CH ₃ ) ₂ C≡C, CH(CF ₃ )CH ₂ , CH(CH ₃ )CH ₂ O, CH ₂ CH ₂ O, CH(cPr)CH ₂ O, CH(CH ₂ OCH ₃ ), CH(CH ₂ CH ₂ SCH ₃ ), CH (COOH), CH(COOCH ₃ ), CH(COOH)CH ₂ , CH(COOCH ₃ )CH ₂ , CH ₂ COH(CF ₃ ), CH(CONHCH _{3 ), CH(CONHCH 3 )} CH ₂ and CH ₂ CH ₂ CONHCH ₂ is a compound of formula (I) selected from the group consisting of divalent units from the group consisting of 2.

Further preferred compounds according to the invention are those in which R ⁸ to R ¹³ are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO ₂ R ^e , CONR ^b R ^d or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₅ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, each substituted by m groups from the group consisting of fluorine, or (C ₁ -C ₆ )-Alkoxy, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-alkenyloxy, (C ₃ -C ₆ )-alkynyloxy, (C ₁ -C ₃ )-alkylsulfinyl , (C ₁ -C ₃ )-alkylsulfonyl, (C ₁ -C ₃ )-alkylthio, each substituted by m groups from the group consisting of fluorine, of the formula This is the compound (I).

Similarly, preferred compounds according to the invention are such that R ⁸ to R ¹³ are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO ₂ R ^e , CONR ^b R ^d or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₅ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, each substituted by m groups from the group consisting of fluorine, or ( C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-alkenyloxy, (C ₃ -C ₆ )-alkynyloxy (each from the group consisting of fluorine) m groups).

Similarly, preferred compounds according to the invention are those in which R ⁸ to R ¹³ are each independently hydrogen, fluorine, chlorine, CO ₂ R ^e , CONR ^b R ^d or (C ₁ -C ₆ )-alkyl(fluorine (substituted by m groups from the group consisting of fluorine); or (C ₁ -C ₆ )-alkoxy (substituted by m groups from the group consisting of fluorine) , is a compound of formula (I).

In particular, R ⁸ to R ¹³ are each independently selected from the group consisting of halogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₃ )-alkoxy and CO ₂ ^Re .

Further preferred compounds according to the invention are those in which Y is hydrogen, cyano, hydroxyl, Z or (C ₁ -C ₁₂ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₁₂ )-alkenyl or (C ₂ -C ₁₂ )-alkynyl, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, Z, CO ₂ R ^e and CONR ^b R ^h A compound of formula (I) selected from the group consisting of

Similarly, preferred compounds according to the invention are those in which Y is hydrogen, cyano, hydroxyl, Z or (C ₁ -C ₁₂ )-alkyl and (C ₃ -C ₈ )-cycloalkyl, each of which is fluorine, CO ₂ m groups from the group consisting of R ^e and CONR ^b R ^h ).

Similarly, preferred compounds according to the invention are those in which Y is (C ₁ -C ₁₂ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₁₂ )-alkenyl or (C ₂ -C ₁₂ )-alkenyl. )-alkynyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR ^d , Z, OZ, NHZ, S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , CO ₂ R ^e , CONR ^b R ^h , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e NR ^b SO ₂ NR ^b R ^e , OCONR ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e substituted by m groups. is a compound of formula (I).

Similarly, preferred compounds according to the invention are those in which Y is (C ₁ -C ₁₂ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₁₂ )-alkenyl or (C ₂ -C _{12 )} -alkenyl. )-alkynyl, each substituted by m groups from the group consisting of fluorine and CO ₂ R ^e .

In particular, Y is Z, or (C ₁ -C ₁₂ )-alkyl and (C ₃ -C ₈ )-cycloalkyl, each of which is fluorine, (C ₁ -C ₂ )-alkoxy, CO ₂ R ^e and CONR ^b ) substituted with m groups from the group consisting of R ^h ).

According to one preferred embodiment, Y is Z.

Preferred compounds according to the invention are those in which Z is a 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring (including phenyl) formed from r carbon atoms and n oxygen atoms. CO ₂ R ^e , CONR ^b R ^h , S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e , NR ^b SO ₂ NR ^b R ^e , OCONR ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e , R ^b , R ^c , R ^e and R ^f substituted by m groups, and n carbon atoms It is a compound of formula (I) having an oxo group of

Similarly, preferred compounds according to the invention are those in which Z is a 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring formed from r carbon atoms and n oxygen atoms. (excluding phenyl), each substituted with m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e and R ^f , a compound of formula (I) in which the carbon atom has n oxo groups.

Further preferred compounds according to the invention are those in which Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms and CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO _{2 3-} , 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated, substituted by m groups from the group consisting of R ^a , R ^b , R ^c , R ^e and R ^f A compound of formula (I) selected from the group consisting of saturated or aromatic rings (excluding phenyl), in which the sulfur atom and the carbon atom bear n oxo groups.

Representative examples of the above 3, 4, 5 or 6 membered saturated, partially unsaturated, fully unsaturated or aromatic rings are the following structures:

Representative examples of the above 4, 5 or 6 membered saturated, partially unsaturated, fully unsaturated or aromatic rings are the following structures:

Similarly, preferred compounds according to the invention are such that Z is selected from the group consisting of a 4- or 5-membered saturated or partially unsaturated ring formed from r carbon atoms and n oxygen atoms, each of which A compound of formula (I) substituted by m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f be.

Similarly, preferred compounds according to the invention are such that Z is selected from the group consisting of a 4- or 5-membered saturated or partially unsaturated ring formed from r carbon atoms and n oxygen atoms, each of which A compound of formula (I) substituted by m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e and R ^f .

Similarly, preferred compounds according to the invention are such that Z is selected from the group consisting of a 5-membered saturated or partially unsaturated ring formed from 4 carbon atoms and 1 oxygen atom, each of which contains CO ₂ A compound of formula (I) substituted by m groups from the group consisting of R ^e , CONR ^b R ^h , CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f .

Similarly, preferred compounds according to the invention are such that Z is selected from the group consisting of a 5-membered saturated or partially unsaturated ring formed from 4 carbon atoms and 1 oxygen atom, each of which contains CO ₂ A compound of formula (I) substituted by m groups from the group consisting of R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e and R ^f .

4, each substituted by m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f as defined above; A representative example of a 5-membered saturated or partially unsaturated ring formed from a carbon atom and one oxygen atom is the structure below, where the arrow indicates a bond to any of the substituents described. :

4, each substituted by m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f as defined above; A preferred example of a 5-membered saturated or partially unsaturated ring formed from a carbon atom and one oxygen atom is the structure below, where the arrow points to any of the described substituents, preferably Showing the bond to CO ₂ ^Re :

4 carbon atoms and 1 oxygen, each substituted by m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e and R ^f as defined above A preferred example of a 5-membered saturated or partially unsaturated ring formed from atoms is the structure below, where the arrow indicates a bond to any of the described substituents, preferably to CO ₂ R ^e Show:

Similarly, preferred compounds according to the invention are such that Z is selected from the group consisting of a 5-membered saturated or partially unsaturated ring formed from 5 carbon atoms , each of which is CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f , which are substituted by m groups from the group consisting of R f .

Similarly, preferred compounds according to the invention are such that Z is selected from the group consisting of a 5-membered saturated or partially unsaturated ring formed from 5 carbon atoms, each of which is CO ₂ R ^e , CONR ^b R A compound of formula (I), substituted by m groups from the group consisting of ^h , R ^b , R ^c , R ^e and R ^f .

5, each substituted by m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f as defined above; A representative example of a 5-membered saturated or partially unsaturated ring formed from carbon atoms is the structure below, where the arrow indicates the bond to any of the substituents described:

5, each substituted by m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f as defined above; Further representative examples of 5-membered saturated or partially unsaturated rings formed from carbon atoms are the structures below, where the arrow indicates the bond to any of the described substituents:

5, each substituted by m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f as defined above; A preferred example of a 5-membered saturated or partially unsaturated ring formed from carbon atoms is the structure below, where the arrow points to any of the described substituents, preferably to CO ₂ R ^e. Showing the join:

formed from 5 carbon atoms, each substituted by m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e and R ^f as defined above A preferred example of a 5-membered saturated or partially unsaturated ring is the structure below, where the arrow indicates a bond to any of the described substituents, preferably to CO ₂ ^Re :

In particular, Z is selected from the group consisting of cyclobutyl, cyclopentyl, cyclopentenyl and tetrahydrofuranyl, respectively, CO ₂ ^Re , CONR ^{b Rh} , CONR ^e SO ₂ ^{Ra , R b ,} R ^c , ^Re and substituted by m groups from the group consisting of R ^f .

Very particularly Z is selected from the group consisting of cyclobutyl, cyclopentyl, cyclopentenyl and tetrahydrofuranyl, each of which is selected from the group consisting of CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e and R ^f is substituted by m groups from .

Preferred examples Z, each substituted by m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f as defined above. .1 to Z.5 are the structures below, where arrow (1) represents the site of attachment to X, and arrows (2) and (3) indicate attachment to any of the described substituents In particular, the bonds to CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e and R ^f are shown:

Preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings:
R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-Haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, ( C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy;
R ² is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
R ³ is hydrogen, halogen, nitro, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, hydroxy-(C ₁ -C ₃ )-alkyl, (C ₃ - _C5 )-cycloalkyl, ( _C3 - _C5 )-halocycloalkyl, hydroxy-( _C3 - _C5 )-cycloalkyl, (C1 _{- C3} )-alkoxy, ( _C1 - _C3 )- Haloalkoxy, (C ₁ -C ₃ )-alkoxycarbonyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkylthio, (C ₁ - C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl;
^R4 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C4 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
R ⁵ is hydrogen, halogen, nitro, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, hydroxy-(C ₁ -C ₃ )-alkyl, (C ₃ - _C5 )-cycloalkyl, ( _C3 - _C5 )-halocycloalkyl, hydroxy-( _C3 - _C5 )-cycloalkyl, (C1 _{- C3} )-alkoxy, ( _C1 - _C3 )- Haloalkoxy, (C ₁ -C ₃ )-alkoxycarbonyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkylthio, (C ₁ - C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl;
R ⁶ is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond (X ⁰ ), or (X ¹ ), (X ² ), (X ³ ), (X ⁴ ), (X ⁵ ) and (X ⁶ ):

is a divalent unit from the group consisting of;
R ⁸ to R ¹³ are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO ₂ R ^e , CONR ^b R ^d , R ^a , or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₅ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, each from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano. m groups), or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ -C ₆ )-alkynyloxy (each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C ₁ -C ₂ )-alkoxy);
Y is hydrogen, cyano, hydroxyl, Z,
or
(C ₁ -C ₁₂ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₁₂ )-alkenyl or (C ₂ -C ₁₂ )-alkynyl, each of which represents fluorine, chlorine, Bromine, iodine, cyano, hydroxyl, OR ^d , Z, OZ, NHZ, S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , CO ₂ R ^e , CONR ^b R ^h , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e NR ^b SO ₂ NR ^b R ^e , OCONR ^b substituted by m groups from the group consisting of R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e ;
Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring (other than ^phenyl ) substituted by m groups from the group consisting of and carbon atoms have n oxo groups;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by m groups;
R ^b is hydrogen or R ^a ;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ -C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^d is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^e is R ^d ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-alkoxycarbonyl-( _C1 - _C6 )-alkyl or ( _C2 - _C4 )-alkynyl, each selected from the group consisting of fluorine, chlorine, bromine, cyano and ( _C1 - _C2 )-alkoxy substituted by m groups;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1 or 2;
r is 1, 2, 3, 4, 5 or 6;
Where the compound of formula (I) has a carboxyl group, including their agriculturally acceptable salts, amides, esters or thioesters , 5 -methyl-3-phenyl-1,4,2-dioxazole-5- Excludes carboxamides.

Preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings:
R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-alkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-alkoxy, preferably hydrogen, (C ₁ -C ₃ )-alkyl or (C ₃ -C ₄ )-cycloalkyl, more preferably hydrogen;
R ² is hydrogen;
R ³ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁴ is hydrogen or fluorine, preferably hydrogen;
R ⁵ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁶ is hydrogen;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond;
Y is Z;
Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring (other than ^phenyl ) substituted by m groups from the group consisting of and carbon atoms have n oxo groups;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by m groups;
R ^b is hydrogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. is substituted by m groups;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-alkoxycarbonyl-( _C1 - _C6 )-alkyl or ( _C2 - _C4 )-alkynyl, each selected from the group consisting of fluorine, chlorine, bromine, cyano and ( _C1 - _C2 )-alkoxy substituted by m groups;
r is 1, 2, 3, 4, 5 or 6;
n is 0, 1 or 2;
m is 0, 1, 2, 3, 4 or 5.

Further preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings: R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cyclo Alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-alkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )- alkyl, (C ₁ -C ₃ )-alkoxy, preferably hydrogen, (C ₁ -C ₃ )-alkyl or (C ₃ -C ₄ )-cycloalkyl, more preferably hydrogen;
R ² is hydrogen;
R ³ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁴ is hydrogen or fluorine, preferably hydrogen;
R ⁵ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁶ is hydrogen;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond;
Y is Z;
Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms and is substituted by m groups from the group consisting of CO ₂ R ^e , a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring (excluding phenyl), the sulfur and carbon atoms having n oxo groups;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₃ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy. ;
r is 1, 2, 3, 4, 5 or 6;
n is 0, 1 or 2;
m is 0, 1, 2, 3, 4 or 5.

Further preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings: R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cyclo Alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-alkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )- alkyl, (C ₁ -C ₃ )-alkoxy, preferably hydrogen, (C ₁ -C ₃ )-alkyl or (C ₃ -C ₄ )-cycloalkyl, more preferably hydrogen;
R ² is hydrogen;
R ³ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁴ is hydrogen or fluorine, preferably hydrogen;
R ⁵ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁶ is hydrogen;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond;
Y is Z;
Z is a 5-membered saturated, partially unsaturated or fully unsaturated group substituted by m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e and R ^f is a carbon ring;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by m groups;
R ^b is hydrogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. is substituted by m groups;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-alkoxycarbonyl-( _C1 - _C6 )-alkyl or ( _C2 - _C4 )-alkynyl, each selected from the group consisting of fluorine, chlorine, bromine, cyano and ( _C1 - _C2 )-alkoxy substituted by m groups;
m is 0, 1, 2 or 3.

Further preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings: R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cyclo Alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-alkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )- alkyl, (C ₁ -C ₃ )-alkoxy, preferably hydrogen, (C ₁ -C ₃ )-alkyl or (C ₃ -C ₄ )-cycloalkyl, more preferably hydrogen;
R ² is hydrogen;
R ³ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁴ is hydrogen or fluorine, preferably hydrogen;
R ⁵ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁶ is hydrogen;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond;
Y is Z;
Z is a 5-membered saturated, partially unsaturated or fully unsaturated carbocycle substituted by m groups from the group consisting of CO ₂ Re ^{and R b ;}
R ^b is hydrogen or (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by selected m groups;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₃ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy. ;
m is 0, 1, 2, or 3.

Further preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings: R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cyclo Alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-alkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )- alkyl, (C ₁ -C ₃ )-alkoxy, preferably hydrogen, (C ₁ -C ₃ )-alkyl or (C ₃ -C ₄ )-cycloalkyl, more preferably hydrogen;
R ² is hydrogen;
R ³ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁴ is hydrogen or fluorine, preferably hydrogen;
R ⁵ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁶ is hydrogen;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond;
Y is (C ₁ -C ₈ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₈ )-alkenyl or (C ₂ -C ₈ )-alkynyl, each of which has fluorine and CO ₂ R ^e ;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
m is 0, 1, 2, or 3.

Further preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings: R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cyclo Alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-alkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )- alkyl, (C ₁ -C ₃ )-alkoxy, preferably hydrogen, (C ₁ -C ₃ )-alkyl or (C ₃ -C ₄ )-cycloalkyl, more preferably hydrogen;
R ² is hydrogen;
R ³ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁴ is hydrogen or fluorine, preferably hydrogen;
R ⁵ is halogen, cyano, (C ₁ -C ₃ )-alkyl, preferably fluorine or chlorine;
R ⁶ is hydrogen;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond;
Y is (C ₁ -C ₈ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₈ )-alkenyl or (C ₂ -C ₈ )-alkynyl, each of which has fluorine , chlorine, bromine, iodine, cyano, hydroxyl, OR ^d , Z, OZ, NHZ, S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , CO ₂ R ^e , CONR ^b R ^h , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e NR ^b SO ₂ NR ^b R ^e , OCONR ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e ;
Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring (other than ^phenyl ) substituted by m groups from the group consisting of and carbon atoms have n oxo groups;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by m groups;
R ^b is hydrogen, (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. is substituted by m groups;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^d is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-alkoxycarbonyl-( _C1 - _C6 )-alkyl or ( _C2 - _C4 )-alkynyl, each selected from the group consisting of fluorine, chlorine, bromine, cyano and ( _C1 - _C2 )-alkoxy substituted by m groups;
r is 1, 2, 3, 4, 5 or 6;
m is 0, 1, 2, or 3;
n is 0, 1 or 2.

Further preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings: R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cyclo Alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ ) -haloalkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy;
R ² is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
^R3 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C5 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R4 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C4 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R5 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C5 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
R ⁶ is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
R ⁷ is (C ₁ -C ₂ )-alkyl, cyclopropyl, (C ₁ -C ₂ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₁ -C ₂ )-alkoxy;
X is a bond (X ⁰ ) or (X ¹ ), (X ² ), (X ³ ), (X ⁴ ), (X ⁵ ) and (X ⁶ ):

is a divalent unit from the group consisting of;
R ⁸ to R ¹³ are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO ₂ R ^e , CONR ^b R ^d , R ^a , or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₅ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, each from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano. m groups), or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ -C ₆ )- )-alkynyloxy (each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C ₁ -C ₂ )-alkoxy);
Y is cyano, hydroxyl, Z,
or
(C ₁ -C ₁₂ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₁₂ )-alkenyl or (C ₂ -C ₁₂ )-alkynyl, each of which represents fluorine, chlorine, Bromine, iodine, cyano, hydroxyl, OR ^d , Z, OZ, NHZ, S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , CO ₂ R ^e , CONR ^b R ^h , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e NR ^b SO ₂ NR ^b R ^e , OCONR ^b substituted by m groups from the group consisting of R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e ;
Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring (other than ^phenyl ) substituted by m groups from the group consisting of and carbon atoms have n oxo groups;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by m groups;
R ^b is hydrogen or R ^a ;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^d is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^e is R ^d ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-alkoxycarbonyl-( _C1 - _C6 )-alkyl or ( _C2 - _C4 )-alkynyl, each selected from the group consisting of fluorine, chlorine, bromine, cyano and ( _C1 - _C2 )-alkoxy substituted by m groups;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1 or 2;
r is 1, 2, 3, 4, 5 or 6.

Further preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings: R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cyclo Alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ ) -haloalkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy;
R ² is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
^R3 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C5 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R4 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C4 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R5 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C5 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
R ⁶ is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
R ⁷ is (C ₁ -C ₂ )-alkyl, cyclopropyl, (C ₁ -C ₂ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₁ -C ₂ )-alkoxy;
X is a bond;
Y is Z or (C ₁ -C ₈ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₈ )-alkenyl or (C ₂ -C ₈ )-alkynyl, respectively is substituted by m groups from the group consisting of fluorine, CO ₂ R ^e and CONR ^e SO ₂ R ^a ;
Z is formed from r carbon atoms, n oxygen atoms, and consists of CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f a 4- to 5-membered saturated or partially unsaturated ring substituted by m groups from the group;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by m groups;
R ^b is hydrogen or (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by selected m groups;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-alkoxycarbonyl-( _C1 - _C6 )-alkyl or ( _C2 - _C4 )-alkynyl, each selected from the group consisting of fluorine, chlorine, bromine, cyano and ( _C1 - _C2 )-alkoxy substituted by m groups;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1 or 2;
r is 1, 2, 3, 4 or 5.

Further preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings: R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cyclo Alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ ) -haloalkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy;
R ² is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
^R3 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C5 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R4 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C4 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R5 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C5 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
R ⁶ is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
R ⁷ is (C ₁ -C ₂ )-alkyl, cyclopropyl, (C ₁ -C ₂ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₁ -C ₂ )-alkoxy;
X is a bond;
Y is Z or (C ₁ -C ₈ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₈ )-alkenyl or (C ₂ -C ₈ )-alkynyl, respectively is substituted by m groups from the group consisting of fluorine and CO ₂ R ^e ;
Z is formed from r carbon atoms, n oxygen atoms and m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e and R ^f a 4- to 5-membered saturated or partially unsaturated ring substituted by;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by m groups;
R ^b is hydrogen or (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by selected m groups;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-alkoxycarbonyl-( _C1 - _C6 )-alkyl or ( _C2 - _C4 )-alkynyl, each selected from the group consisting of fluorine, chlorine, bromine, cyano and ( _C1 - _C2 )-alkoxy substituted by m groups;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1 or 2;
r is 1, 2, 3, 4 or 5.

Further preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings: R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cyclo Alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ ) -haloalkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy;
R ² is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
^R3 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C5 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R4 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C4 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R5 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C5 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
R ⁶ is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond;
Y is Z;
Z is formed from r carbon atoms, n oxygen atoms and m groups from the group consisting of CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e and R ^f a 4- to 5-membered saturated or partially unsaturated ring substituted by;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by m groups;
R ^b is hydrogen or (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by selected m groups;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-alkoxycarbonyl-( _C1 - _C6 )-alkyl or ( _C2 - _C4 )-alkynyl, each selected from the group consisting of fluorine, chlorine, bromine, cyano and ( _C1 - _C2 )-alkoxy substituted by m groups;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1 or 2;
r is 1, 2, 3, 4 or 5.

Further preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings: R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cyclo Alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ ) -haloalkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy;
R ² is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
^R3 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C5 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R4 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C4 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R5 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C4 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
R ⁶ is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond;
Y is (C ₁ -C ₁₂ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₁₂ )-alkenyl or (C ₂ -C ₁₂ )-alkynyl, each of which has fluorine , chlorine, bromine, iodine, cyano, hydroxyl, OR ^d , Z, OZ, NHZ, S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , CO ₂ R ^e , CONR ^b R ^h , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e NR ^b SO ₂ NR ^b R ^e , OCONR ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e ;
Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and CO ₂ R ^e , CONR ^b R ^h , R ^b , R ^c , R ^e a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring (other than ^phenyl ) substituted by m groups from the group consisting of and carbon atoms have n oxo groups;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by m groups;
R ^b is hydrogen or R ^a ;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^d is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^e is R ^d ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-alkoxycarbonyl-( _C1 - _C6 )-alkyl or ( _C2 - _C4 )-alkynyl, each selected from the group consisting of fluorine, chlorine, bromine, cyano and ( _C1 - _C2 )-alkoxy substituted by m groups;
r is 1, 2, 3, 4, 5 or 6;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1 or 2.

Further preferred compounds of the invention are those of formula (I) in which the substituents have the following meanings: R ¹ is hydrogen;
R ² is hydrogen;
R ³ is halogen;
R ⁴ is hydrogen;
R ⁵ is halogen;
R ⁶ is hydrogen;
R ⁷ is (C ₁ -C ₂ )-alkyl, cyclopropyl, (C ₁ -C ₂ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₁ -C ₂ )-alkoxy;
X is a bond;
Y is Z or (C ₁ -C ₈ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₈ )-alkenyl or (C ₂ -C ₈ )-alkynyl, respectively is substituted by m groups from the group consisting of fluorine and CO ₂ R ^e ;
Z is a 4- to 5-membered saturated or partially unsaturated ring formed from r carbon atoms, n oxygen atoms and substituted by m groups from the group consisting of CO ₂ ^Re ; can be;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
r is 4 or 5;
m is 0, 1, 2, 3, 4 or 5;
n is 0 or 1.

Further preferred embodiments (II and I.II) of the compounds of formula (I) are:
(II): R ¹ is hydrogen:

(I.II): R ¹ is methyl:

It is a compound.

Particularly preferred are compounds of formula (IIa) in which R ¹ , R ² and R ⁶ are hydrogen:

Also particularly preferred are compounds of formula (IIb) in which R ¹ , R ² , R ⁴ and R ⁶ are hydrogen:

Particularly preferred are compounds of formula (IIc) in which R ¹ , R ² and R ⁶ are hydrogen, X is a bond (X ⁰ ) and Y is Z:

Also particularly preferred are compounds of formula (IId) in which R ¹ , R ² , R ⁴ and R ⁶ are hydrogen, X is a bond (X ⁰ ) and Y is Z:

Particular preference is also given to compounds of formula (I.II.a) in which R ² and R ⁶ are hydrogen and R ¹ is methyl:

Also particularly preferred are compounds of formula (I.II.b) in which R ² , R ⁴ and R ⁶ are hydrogen and R ¹ is methyl:

In the context of the present invention, compounds in which R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in lines 1 to 768 of Table 1 below are Particularly preferred.

Compounds of formula I.1., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above, Particular preference is thus given to the individual compounds I.1.1 to I.1.768:

Compounds of formula I.2., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.2.1 to I.2.768:

Compounds of formula I.3., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.3.1 to I.3.768:

Compounds of formula I.4., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.4.1 to I.4.768:

Compounds of formula I.5., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is therefore given to the individual compounds I.5.1 to I.5.768:

Compounds of formula I.6., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.6.1 to I.6.768:

Compounds of formula I.7., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above, Particular preference is therefore given to the individual compounds I.7.1 to I.7.768:

Compounds of formula I.8., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.8.1 to I.8.768:

Compounds of formula I.9., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.9.1 to I.9.768:

Compounds of formula I.10., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.10.1 to I.10.768:

Compounds of formula I.11., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is therefore given to the individual compounds I.11.1 to I.11.768:

Compounds of formula I.12., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.12.1 to I.12.768:

Compounds of formula I.13., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is therefore given to the individual compounds I.13.1 to I.13.768:

Compounds of formula I.14., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.14.1 to I.14.768:

Compounds of formula I.15., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.15.1 to I.15.768:

Compounds of formula I.16., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.16.1 to I.16.768:

Compounds of formula I.17., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above, Particular preference is therefore given to the individual compounds I.17.1 to I.17.768:

Compounds of formula I.18., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.18.1 to I.18.768:

Compounds of formula I.19., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.19.1 to I.19.768:

Compounds of formula I.20., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.20.1 to I.20.768:

Compounds of formula I.21., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.21.1 to I.21.768:

Compounds of formula I.22., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.22.1 to I.22.768:

Compounds of formula I.23., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.23.1 to I.23.768:

Compounds of formula I.24., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.24.1 to I.24.768:

Compounds of formula I.25., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.25.1 to I.25.768:

Compounds of formula I.26., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is therefore given to the individual compounds I.26.1 to I.26.768:

Compounds of formula I.27., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.27.1 to I.27.768:

Compounds of formula I.28., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is therefore given to the individual compounds I.28.1 to I.28.768:

Compounds of formula I.29., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above, Particular preference is therefore given to the individual compounds I.29.1 to I.29.768:

Compounds of formula I.30., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.30.1 to I.30.768:

Compounds of formula I.31., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.31.1 to I.31.768:

Compounds of formula I.32., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above, Particular preference is thus given to the individual compounds I.32.1 to I.32.768:

Compounds of formula I.33., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.33.1 to I.33.768:

Compounds of formula I.34., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.34.1 to I.34.768:

Compounds of formula I.35., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.35.1 to I.35.768:

Compounds of formula I.36., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above, Particular preference is thus given to the individual compounds I.36.1 to I.36.768:

Compounds of formula I.37., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above, Particular preference is thus given to the individual compounds I.37.1 to I.37.768:

Compounds of formula I.38., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.38.1 to I.38.768:

Compounds of formula I.39., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.39.1 to I.39.768:

Compounds of formula I.40., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.40.1 to I.40.768:

Compounds of formula I.41., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.41.1 to I.41.768:

Compounds of formula I.42., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above, Particular preference is thus given to the individual compounds I.42.1 to I.42.768:

Compounds of formula I.43., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.43.1 to I.43.768:

Compounds of formula I.44., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above, Particular preference is thus given to the individual compounds I.44.1 to I.44.768:

Compounds of formula I.45., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.45.1 to I.45.768:

Compounds of formula I.46., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above, Particular preference is thus given to the individual compounds I.46.1 to I.46.768:

Compounds of formula I.47., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.47.1 to I.47.768:

Compounds of formula I.48., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.48.1 to I.48.768:

Compounds of formula I.49., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.49.1 to I.49.768:

Compounds of formula I.50., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is therefore given to the individual compounds I.50.1 to I.50.768:

Compounds of formula I.51., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.51.1 to I.51.768:

Compounds of formula I.52., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is therefore given to the individual compounds I.52.1 to I.52.768:

Compounds of formula I.53., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.53.1 to I.53.768:

Compounds of formula I.54., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above, Particular preference is thus given to the individual compounds I.54.1 to I.54.768:

Compounds of formula I.55., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is therefore given to the individual compounds I.55.1 to I.55.768:

Compounds of formula I.56., wherein R ¹ , R ² and R ⁶ are hydrogen and R ³ , R ⁴ , R ⁵ and R ⁷ have the meanings defined in rows 1 to 768 of Table 1 above; Particular preference is thus given to the individual compounds I.56.1 to I.56.768:

The compounds of formula (I) according to the invention can be prepared by standard methods of organic chemistry, for example by the following process:

Compounds of formula (I) can be prepared according to or analogously to methods described in the prior art. The synthesis utilizes starting materials that are commercially available or can be prepared according to conventional procedures starting from readily available compounds.

Compounds of formula (I) can be prepared from carboxylic acids (III) and commercially available amines (II) using organic bases and coupling reagents. Compounds of formula (I) can therefore be combined with coupling reagents (1 to 2 equivalents), such as T ₃ P (propanephosphonic anhydride) or HATU (O-(7-azabenzotriazol-1-yl)-N, N,N'',N'-tetramethyluronium-hexafluorophosphate), organic base (1-3 eq.) and amine (II) (1-3 eq. ) can be synthesized from The reaction is typically carried out in an organic solvent. Preferably aprotic organic solvents are used. Most preferably tetrahydrofuran (THF), N,N-dimethylformamide (DMF) or acetonitrile (ACN) is used. The reaction is carried out at temperatures between 0°C and reflux. Preferably the reaction is carried out at room temperature. Preferably, the organic base is triethylamine or N,N-diisopropylethylamine.

Carboxylic acids (III) are commercially available or can be prepared from the corresponding esters (IV) (R ^p is alkyl or benzyl). When R ^p is alkyl, the esters (IV) can be cleaved using aqueous alkali metal hydroxides. Preferably, lithium hydroxide, sodium hydroxide or potassium hydroxide (1-2 equivalents) are used. The reaction is typically carried out in a mixture of water and an organic solvent. Preferably, the organic solvent is THF, methanol or acetonitrile. The reaction is carried out at a temperature between 0° C. and 100° C. Preferably, the reaction is carried out at room temperature. When R ^p is benzyl in (IV), the ester can be cleaved using palladium on charcoal (0.001-1 equivalent) as catalyst and hydrogen gas at a temperature between 0° C. and reflux. Preferably, the reaction is carried out at room temperature. Typically, an organic solvent is used. Preferably, THF, methanol or ethanol is used.

The ester (IV) was prepared from N-hydroxybenzene-1-carbonimidoyl chloride (V) and the 2-oxo-carboxylic acid using a procedure similar to that described in Chem. Ber. 105, 2805-2814 (1972). It can be prepared by combining the esters (VI) in the presence of a base. Preferably, nitrogen-containing bases, such as (C ₁ -C ₆ )-alkylamines, preferably tri-(C ₁ -C ₆ )-alkylamines, such as triethylamine, trimethylamine, N-ethyldiisopropylamine, are added to N-hydroxybenzene. It is used in an amount of 1 to 2 equivalents relative to -1-carbonimidoyl chloride (V). The 2-oxo-carboxylic acid ester (VI) is used in 1-10 equivalents, preferably 2-5 equivalents.

The reaction is typically carried out in an organic solvent. Preferably, the organic solvent is an aromatic hydrocarbon, such as benzene, chlorobenzene, toluene, cresol, or o-, m-, and p-xylene. The reaction is carried out at temperatures between 0°C and 100°C. Preferably, the reaction is carried out at room temperature.

N-Hydroxybenzene-1-carbonimidoyl chloride (V) can be obtained commercially or by known methods (e.g. WO12130798, WO1404882, WO14048882, WO18228985, WO18228986, WO19034602, or WO19145245, and the references described therein). (Reference).

R ⁷ of compound (I), (III) or (IV) can be further modified synthetically by known methods.

In order to widen the spectrum of action, the compounds of formula (I) may be mixed with a number of representatives of other herbicidal or growth-regulating active ingredients and then applied simultaneously. Suitable components for the combination are, for example, acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofurans, benzoic acids, benzothiadiazinones, bipyridyliums, carbamates, chloroacetamides, Chlorocarboxylic acid type, cyclohexanedione type, dinitroaniline type, dinitrophenol type, diphenyl ether type, glycine type, imidazolinone type, isoxazole type, isoxazolidinone type, nitrile type, N-phenylphthalimide type, oxadiazole type, oxazolidine type Dione type, oxyacetamide type, phenoxycarboxylic acid type, phenyl carbamate type, phenylpyrazole type, phenylpyrazoline type, phenylpyridazine type, phosphinic acid type, phosphoroamidate type, phosphorodithioate type, phthalamate type, pyrazole type , pyridazinone series, pyridine series, pyridinecarboxylic acid series, pyridinecarboxamide series, pyrimidinedione series, pyrimidinyl(thio)benzoate series, quinolinecarboxylic acid series, semicarbazone series, sulfonylaminocarbonyltriazolinone series, sulfonylurea series, tetrazolinones It is a herbicide belonging to the following classes: thiadiazole, thiocarbamate, triazine, triazinone, triazole, triazolinone, triazolocarboxamide, triazolopyrimidine, triketone, uracil, and urea.

The compounds of formula (I), alone or in combination with other herbicides or otherwise in the form of a mixture with other crop protection agents, can be used to kill, for example, pests or phytopathogenic fungi or bacteria. It may furthermore be advantageous to apply together with agents for control. Also of interest is its miscibility with inorganic salt solutions used to treat nutritional deficiencies and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates can also be added.

In one embodiment of the invention, the combination according to the invention comprises at least one compound of formula (I) (compound A or component A) and a herbicide B, preferably of classes b1) to b15). (Compound B), and safener C (Compound C).

In another embodiment of the invention, the combination according to the invention comprises at least one compound of formula (I) and at least one further active compound B (herbicide B).

Examples of herbicides B that can be used in combination with compounds A of formula (I) according to the invention are:

b1) From the group of lipid biosynthesis inhibitors:
ACC-herbicides, such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop (cyhalofop), cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P (fenoxaprop-P), fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl ( fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden ( pinoxaden), profoxydim, propaquizafop, Quizalofop, Quizalofop-ethyl, Quizalofop-tefuryl, Quizalofop-P, Quizalofop-P -ethyl (quizalofop-P-ethyl), quizalofop-P-tefuryl (sethoxydim), tepraloxydim (tepraloxydim), tralkoxydim (tralkoxydim), 4-(4'-chloro-4- Cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS1312337-72 -6);4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H- Pyran-3(6H)-one (CAS1312337-45-3);4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy- 2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS1033757-93-5);4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl ]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS1312340-84-3);5-(acetyloxy)-4-( 4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3 -one (CAS1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6 -dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1' -biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1312340-82-1);5-(acetyloxy)-4- (2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1033760-55-2);4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6 ,6-tetramethyl-5-oxo-2H-pyran-3-yl(carboxylic acid methyl ester (CAS1312337-51-1);4-(2',4'-dichloro-4-cyclopropyl-[1,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl(carboxylic acid methyl ester; 4-(4'- Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3 -yl(carboxylic acid methyl ester (CAS1312340-83-2);4-(2',4'-dichloro-4-ethyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro- 2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl (carboxylic acid methyl ester (CAS1033760-58-5); as well as non-ACC herbicides such as benfuresate, butylate ), cycloate, dalapon, dimepiperate, EPTC, esprocarb, etofumesate, flupropanate, molinate, orbencarb, pebulate , prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;

b2) From the group of ALS inhibitors:
Sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlor Chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron , flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl methyl), imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron ( mesosulfuron), metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron -sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl methyl), trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron,
Imidazolinones, such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imzapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides, such as chloransulam, chloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pirimisul pyrimisulfan and pyroxsulam,
Pyrimidinyl benzoates, such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac -Sodium (pyrithiobac-sodium), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1-methylethyl ester (CAS420138-41-6 ), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]-methyl]amino]-benzoic acid propyl ester (CAS420138-40-5), N-(4-bromophenyl )-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS420138-01-8),
Sulfonylaminocarbonyl-triazolinone herbicides, such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone- thiencarbazone-methyl; and triafamone.
Among these, preferred embodiments of the invention relate to compositions comprising at least one imidazolinone herbicide;

b3) From the group of photosynthesis inhibitors:
Amicarbazone, inhibitor of photosystem II, such as 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744 -66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert -butyl-1-methyl-pyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl -1-Methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5- Methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl] Fluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl] Imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22- 2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1- (5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1), chlorotriazine series, triazinone ( Triazine herbicides such as triazinone, triazindione, methylthiotriazine and pyridazinone, such as ametryn, atrazine, chloridazone, cyanazine. (cyanazine), desmetrin, dimethametryn, hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumetone (terbumeton), terbuthylazin, terbutryn and trietazin, aryl ureas such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron , fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenylcarbamates such as desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl ( phenmedipham-ethyl), nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uracils such as bromacil, lenacil ) and terbacil, as well as bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil, and inhibitors of photosystem I, e.g. diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimethylsulfate. Among these, preferred embodiments of the invention relate to compositions comprising at least one arylurea herbicide. Among these, likewise preferred embodiments of the invention relate to compositions comprising at least one triazine herbicide. Among these, likewise preferred embodiments of the invention relate to compositions comprising at least one nitrile herbicide;

b4) From the group of protoporphyrinogen-IX oxidase inhibitors:
acifluorfen, acifluorfen-sodium, azafenidine, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone (carfentrazone), carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr ), flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen- ethyl), fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, Pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, thiafenacil (tiafenacil), trifludimoxazin, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3, 4-Tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy) -5-Methyl-1H-pyrazole-1-carboxamide (CAS452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole -1-carboxamide (CAS915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS452099-05 -7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS452100-03-7), 3- [7-Fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo- [1,3,5]triazinane-2,4-dione (CAS451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4- Dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione (CAS1300118-96-0), 1-methyl-6-tri Fluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H- Pyrimidine-2,4-dione (CAS1304113-05-0), methyl(E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl ]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (CAS948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazole -4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS212754-02-4), 2-[2-chloro-5-[3-chloro-5 -(Trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-acetic acid methyl ester (CAS1970221-16-9), 2-[2-[[3-chloro-6-[3,6 -dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS2158274-96- 3), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5 -Fluoro-2-pyridinyl]oxy]phenoxy]acetic acid ethyl ester (CAS158274-50-9), methyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5- Oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS2271389-22-9), ethyl 2-[[3-[2-chloro-5 -[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS2230679-62-4 ), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5 -Fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS2158275-73-9), 2-[[3-[[3-chloro-6-[3,6-dihydro-3 -Methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]acetic acid ethyl ester (CAS2158274-56- 5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5 -Fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3 -Methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)- Acetamide (CAS2158276-22-1);

b5) From the group of bleaching herbicides:
PDS inhibitors: beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethyl) Phenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone , fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen , sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, whitening agent, unknown target: aclonifen, amitrole, flumeturon ), 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), bixlozone and 2-(2 ,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7);

b6) From the group of EPSP synthase inhibitors:
glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate);

b7) From the group of glutamine synthase inhibitors:
bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammonium;

b8) From the group of the DHP synthase inhibitors:
Asulam;

b9) From the group of mitotic inhibitors:
Compounds of group K1: dinitroanilines, such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamines ( prodiamine) and trifluralin, phosphoramidates such as amiprophos, amiprophos-methyl and butamiphos, benzoic acid herbicides such as chlorthal, chlorthal-dimethyl -dimethyl), pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, furam flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl methyl) and propham, among these compounds of group K1, especially dinitroanilines, are preferred;

b10) From the group of VLCFA inhibitors:
Chloroacetamides, such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor ( metazachlor, metolachlor, metolachlor-S, petoxamide, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilide series , such as flufenacet and mefenacet, acetanilides such as diphenamide, naproanilide, napropamide and napropamide-M, tetrazolinones such as fentrazamide (fentrazamide), as well as other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, and formula II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8, and II.9:

isoxazoline compounds,
(Isoxazoline compounds of formula (II) are known in the art, for example from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576);
Among VLCFA inhibitors, chloroacetamide and oxyacetamide are preferred;

b11) From the group of cellulose biosynthesis inhibitors:
Chlorthiamide, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, and 1-cyclohexyl-5-pentafluorophenyloxy-1 ⁴ -[1,2, 4,6]Thiatriazin-3-ylamine (CAS175899-01-1);

b12) From the group of decoupler herbicides:
dinoseb, dinoterb and DNOC and its salts;

b13) From the group of auxin herbicides:
2,4-D and its salts and esters, such as clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts, such as Aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid ( clopyralid) and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, Flopyrauxifen (flopyrauxifen), fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac (quinclorac), quinmerac, TBA(2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS1390661 -72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS1629965-65-6);

b14) From the group of auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) From the group of other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-methylsulfate, dimethipin, DSMA, dymron , endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozolin, methyl azide, methyl bromide, methyl-dymron, Methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine tetoflupyrrolimet and tridiphane.

Furthermore, it may be useful to apply compounds of formula (I) in combination with safeners. A safener is a chemical compound that prevents or reduces damage to useful plants without significantly affecting the herbicidal action of the compounds of formula (I) on undesirable vegetation. They can be applied either before sowing (eg seed treatment, shoots or seedlings) or by pre- or post-emergence application of useful plants. The safener and the compound of formula (I) and optionally the herbicide B can be applied simultaneously or sequentially.

In another embodiment of the invention, the combination according to the invention comprises at least one compound of formula (I) and at least one safener C (component C).

Examples of safeners are (quinoline-8-oxy)acetic acid, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acid, 1-phenyl-4,5-dihydro-5 -Alkyl-1H-pyrazole-3,5-dicarboxylic acid, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acid, dichloroacetamide, alpha-oximinophenyl acetonitrile, acetophenone oxime, 4,6- Dihalo-2-phenylpyrimidine, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic acid amide, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazole Carboxylic acids, phosphorothiolates and N-alkyl-O-phenyl carbamates, and their agriculturally acceptable salts and their agriculturally acceptable derivatives, such as amides, esters and thioesters, provided that they contain an acid group. It is.

Examples of safeners Compound C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, phenyl. Chlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4- (dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148) , CAS52836-31-4), metcamifen and BPCMS (CAS54091-06-4).

The active compounds B and C of groups b1) to b15) are known herbicides and safeners, for example The Compendium of Pesticide Common Names (http: //www.alanwood.net/pesticides/);Farm Chemicals Handbook 2000 Volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Supplement to the Herbicide Handbook, 7th Edition, Weed Science Society of America, 1998. 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CAS No. 52836-31-4] is also called R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also called AD-67 and MON4660.

The assignment of active compounds to each mode of action is based on current knowledge. If several modes of action apply to one active compound, the substance was assigned to only one mode of action.

The invention also relates to formulations comprising at least an auxiliary agent and at least one compound of formula (I) according to the invention.

The formulation contains a pesticidally effective amount of a compound of formula (I). The term "effective amount" is defined as an amount sufficient to control undesirable vegetation, especially undesirable vegetation in a crop (i.e., a cultivated plant), but which does not cause substantial damage to the crop plant being treated. indicates the amount of the combination or compound of formula (I) that is not present. This amount can vary over a wide range and depends on various factors such as the undesirable vegetation to be controlled, the crop plant or material to be treated, the climatic conditions and the particular compound of formula (I) used. It is determined.

The compounds of formula (I), their salts, amides, esters or thioesters, can be used in formulations of the customary types, such as solutions, emulsions, suspensions, powders, powders, pastes, granules, compresses, capsules and the like. can be converted into a mixture of Examples of formulation types are suspensions (e.g. SC, OD, FS), emulsions (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, fragrances. agents, hydrated powders or hydrated powders (e.g. WP, SP, WS, DP, DS), compaction agents (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), Insecticidal products (eg LN) as well as gel formulations (eg GF) for the treatment of plant propagation materials, eg seeds. These and further formulation types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Edition, May 2008, CropLife International.

The formulation may be prepared using methods such as those described by Mollet and Grubemann in Formulation technology, Wiley VCH, Weinheim, 2001; or as described by Knowles in New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. Prepared in a known manner.

Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, Humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericidal agents, antifreeze agents, antifoaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers include water and organic solvents such as medium to high boiling mineral oil fractions (e.g. kerosene, diesel oil); oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons (e.g. alcohols (e.g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol); glycols; DMSO; ketones (e.g. cyclohexanone); esters (e.g. lactic acid esters, carbonate esters, fatty acid esters, gamma-butyrolactone); fatty acids; phosphonates; amines; amides (eg, N-methylpyrrolidone, fatty acid dimethylamide); and mixtures thereof.

Suitable solid carriers or fillers include mineral earths (e.g. silicates, silica gels, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide); polysaccharides (e.g. cellulose, starch); fertilizers (eg ammonium sulfate, ammonium phosphate, ammonium nitrate, urea); products of plant origin (eg flour, bark flour, wood flour, nut husk flour), and mixtures thereof.

Suitable surfactants are surface-active compounds such as anionic surfactants, cationic surfactants, nonionic surfactants and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, (2008) (International or North American Edition).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, dodecylbenzene and tridecylbenzene. sulfonates, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, or sulfates of fatty acid esters. Examples of phosphates are phosphoric acid esters. Examples of carboxylates are alkyl carboxylates and also carboxylated alcohols or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated from 1 to 50 equivalents. Ethylene oxide and/or propylene oxide (preferably ethylene oxide) can be used for the alkoxylation. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds having one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are block polymers of type A-B or A-B-A comprising blocks of polyethylene oxide and polypropylene oxide, or block polymers of type A-B-C comprising alkanols, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are polyacrylic acids or alkali salts of polyacid comb polymers. Examples of polybases are polyvinylamine or polyethyleneamine.

Suitable adjuvants are compounds that have negligible or no pesticidal activity in themselves and enhance the biological performance of the compound of formula (I) against the target. . Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are given by Knowles in Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified clays), polycarboxylates and silicates.

Preferred bactericides are bronopol and isothiazolinone derivatives (eg alkylisothiazolinones and benzisothiazolinones).

Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable antifoam agents are silicones, long chain alcohols and salts of fatty acids.

Suitable colorants (eg red, blue, or green colorants) are poorly water-soluble pigments and water-soluble dyes. Examples include inorganic colorants (eg iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (eg alizarin colorant, azo colorant and phthalocyanine colorant).

Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples of formulation types and their preparation are as follows:

i) water-soluble concentrates (SL, LS)
10 to 60% by weight of a compound of formula (I) according to the invention, or selected from at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a safener C (component C) and at least one further compound, and 5 to 15% by weight of a wetting agent (e.g. an alcohol alkoxylate) dissolved in up to 100% by weight of water and/or a water-soluble solvent (e.g. an alcohol). . The active substance dissolves when diluted with water.

ii) dispersible concentrates (DC)
5 to 25% by weight of a compound of formula (I) according to the invention, or selected from at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a safener C (component C) and at least one further compound, and 1 to 10% by weight of a dispersant (eg polyvinylpyrrolidone) is dissolved in up to 100% by weight of an organic solvent (eg cyclohexanone). Dilution with water gives a dispersion.

iii) emulsifiable concentrates (EC)
15 to 70% by weight of a compound of formula (I) according to the invention, or selected from at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a safener C (component C) and 5 to 10% by weight of an emulsifier (e.g. calcium dodecylbenzene sulfonate and castor oil ethoxylate) in an amount of up to 100% by weight of a water-insoluble organic solvent (e.g. soluble in aromatic hydrocarbons). Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)
5 to 40% by weight of a compound of formula (I) according to the invention, or selected from at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a safener C (component C) at least one further compound, and 1 to 10% by weight of an emulsifier (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate), and 20 to 40% by weight of a water-insoluble organic solvent ( eg aromatic hydrocarbons). This mixture is introduced into up to 100% by weight water using an emulsifier to form a homogeneous emulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)
20 to 60% by weight of a compound of formula (I) according to the invention or at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a herbicidal compound B (component B) in a ball mill under stirring. and at least one further compound selected from Agent C (component C), 2 to 10% by weight of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylates), 0.1 to 2 Grinding with the addition of % by weight of a thickener (for example xanthan gum) and up to 100 % by weight of water gives a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. For FS type formulations up to 40% by weight of a binder (eg polyvinyl alcohol) is added.

vi) water-dispersible granules and water-soluble granules (WG, SG)
from 50 to 80% by weight of a compound of formula (I) according to the invention or of at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a safener C (component C) The combination comprising at least one further selected compound is comminuted with the addition of up to 100% by weight of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylates) and processed in specialized equipment (e.g. It is prepared as water-dispersible or water-soluble granules using an extruder, spray tower, or fluidized bed. Dilution with water gives a stable dispersion or solution of the active substance.

vii) water-dispersible powders and water-soluble powders (WP, SP, WS)
In a rotor-stator mill, 50 to 80% by weight of a compound of formula (I) according to the invention or at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a safener C. (component C), 1 to 5% by weight of a dispersing agent (e.g. sodium lignosulfonate), 1 to 3% by weight of a wetting agent (e.g. (alcohol ethoxylate) and up to 100% by weight of a solid support (eg silica gel). Dilution with water gives a stable dispersion or solution of the active substance.

viii) Gel (GW, GF)
5 to 25% by weight of a compound of formula (I) according to the invention, or at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a herbicidal compound B (component B) in a ball mill under stirring. and at least one further compound selected from Agent C (component C). (e.g. carboxymethylcellulose) and up to 100% by weight of water to obtain a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

iv) Microemulsion (ME)
5 to 20% by weight of a compound of formula (I) according to the invention, or selected from at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a safener C (component C) and at least one further compound containing 5-30% by weight of an organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylates) and up to 100% water. The mixture is stirred for 1 hour to spontaneously form a thermodynamically stable microemulsion.

iv) Microcapsules (CS)
5 to 50% by weight of a compound of formula (I) according to the invention, or selected from at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a safener C (component C) 0-40% by weight of water-insoluble organic solvents (e.g. aromatic hydrocarbons), 2-15% by weight of acrylic monomers (e.g. methyl methacrylate, methacrylic The oil phase containing the acid and diacrylate or triacrylate is dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, 5 to 50% by weight of a compound of formula (I) according to the invention, 0 to 40% by weight of a water-insoluble organic solvent (e.g. an aromatic hydrocarbon) and an isocyanate monomer (e.g. diphenylmethene-4 , 4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol). Addition of a polyamine (eg hexamethylene diamine) results in the formation of polyurea microcapsules. The monomers amount to a total amount of 1 to 10% by weight. Weight % refers to total CS formulation.

ix) Dustable powders (DP, DS)
1 to 10% by weight of a compound of formula (I) according to the invention, or selected from at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a safener C (component C) The combination containing at least one further compound, which is prepared by the chemistries, is milled and intimately mixed with up to 100% by weight of a solid carrier (eg, milled kaolin).

x) Granules (GR, FG)
0.5 to 30% by weight of a compound of formula (I) according to the invention, or selected from at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a safener C (component C) The combination containing at least one further compound, which is prepared by the chemistries, is milled and combined with up to 100% by weight of a solid carrier (eg, a silicate). Granulation is accomplished by extrusion, spray drying, or fluidized bed.

xi) Ultra-low volume liquids (UL)
1 to 50% by weight of a compound of formula (I) according to the invention, or selected from at least one compound of formula (I) (component A) and a herbicidal compound B (component B) and a safener C (component C) and at least one further compound, is dissolved in up to 100% by weight of an organic solvent (eg an aromatic hydrocarbon).

Formulation types i) to xi) optionally contain further auxiliaries (for example 0.1 to 1% by weight bactericide, 5 to 15% by weight antifreeze, 0.1 to 1% by weight antifoaming agent, and 0.1 to 1% by weight antifoaming agent). % colorant).

The formulations and/or combinations generally contain from 0.01 to 95% by weight, preferably from 0.1 to 90% and especially from 0.5 to 75% by weight of the compound of formula (I).

The compounds of formula (I) are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectroscopy).

Solution for seed treatment (LS), suspoemulsion (SE), flowable concentrate (FS), powder for drying (DS), water-dispersible powder for slurry treatment (WS), water-soluble Stable powders (SS), emulsions (ES), emulsions (EC) and gels (GF) are commonly used for the purpose of treating plant propagation material, especially seeds. After dilution 2 to 10 times, the formulation gives an active substance concentration of 0.01 to 60% by weight, preferably 0.1 to 40% by weight, in ready-to-use preparations. (move down)

Methods for applying compounds of formula (I), formulations and/or combinations thereof to plant propagation material (especially seeds) include dressing, coating, pelleting of the propagation material. (pelleting), dusting, soaking and in-furrow. Preferably, the compounds of formula (I), their formulations and/or combinations, respectively, are administered in such a way that germination is not induced (e.g. by seed dusting, seed pelleting, seed coating and seed dusting). ) applied to plant propagation materials.

Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the compound of formula (I). It can be added to the compounds, formulations and/or combinations containing them as a premix or, if appropriate, immediately before use (tank mix). These agents can be mixed with the formulation according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user administers the compounds of formula (I), formulations and combinations containing the same according to the invention, usually in a pre-dosage device, a backpack nebulizer, a spray tank, a spray airplane, or Apply from irrigation system. Usually, the formulation is brought to the desired application concentration with water, buffers and/or further auxiliaries, thus giving a ready-to-use spray solution or formulation according to the invention. Usually 20 to 2000 liters, preferably 50 to 400 liters of ready-to-use spray liquid are applied per hectare of agriculturally useful area.

According to one embodiment, either the individual components or the partially premixed components of the formulation according to the invention include, for example, a compound of formula (I) and optionally from groups B and/or C). The ingredients containing the active substance may be mixed in the spray tank by the user and, if appropriate, further auxiliaries and additives may be added.

In a further embodiment, the individual components of the formulation according to the invention (for example part of a kit or part of a binary or ternary mixture) may be mixed by the user himself in a spray tank, if appropriate. , further auxiliaries may be added.

In a further embodiment, either the individual components or the partially premixed components of the formulation according to the invention, for example a compound of formula (I) and optionally an active substance from groups B and/or C) The components can be applied together (eg, after tank mixing) or sequentially.

The compounds of formula (I) are suitable as herbicides. These are suitable on their own in suitable formulations or in combination with at least one further compound selected from herbicidally active compounds B (component B) and safeners C (component C).

Compounds of formula (I) or formulations and/or combinations containing compounds of formula (I) control undesirable vegetation in non-crop areas very efficiently, especially at high application rates. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, corn, soybean and cotton without causing significant damage to the crop plants. This effect is mainly observed at low application rates.

The compounds of formula (I), or formulations and/or combinations containing them, are applied to plants primarily by spraying the leaves. Application here can be carried out, for example, by conventional spraying techniques using water as carrier and spray liquid volumes of about 100 to 1000 l/ha (eg 300 to 400 l/ha). The compounds of formula (I), or formulations and/or combinations containing them, can also be applied by low-dose or ultra-low-dose methods or in the form of microgranules.

Application of a compound of formula (I), or a formulation and/or combination containing it, can be carried out before, during and/or after emergence of the undesirable vegetation, preferably during and/or after emergence.

Application of the compounds of formula (I) or formulations and/or combinations can be carried out before or during sowing.

The compounds of formula (I) or formulations and/or combinations containing them can be applied pre-emergent, post-emergent or pre-planting, or together with the seeds of crop plants. A compound of formula (I) or a formulation and/or combination containing the same is applied to seeds of crop plants that have been pretreated with the compound of formula (I) or a formulation and/or combination containing the same. It is also possible to apply If the active ingredient is not well tolerated by a particular crop plant, spray equipment may be used to ensure that the active ingredient reaches the foliage of undesirable vegetation growing under the crop plant or the open soil surface. However, application techniques may be used in which the combination is sprayed in such a way that the leaves of susceptible crop plants are sprayed as little as possible (post-directed, lay-by).

In a further embodiment, the compound of formula (I), or formulations and/or combinations containing it, can be applied by treating the seeds. Treatment of the seeds can be carried out by essentially all methods familiar to the person skilled in the art (seed dusting, seed coating) based on compounds of formula (I) or formulations and/or combinations prepared therefrom. method, seed dusting method, seed dipping method, seed film coating method, seed multilayer coating method, seed hull coating method, seed dropping method, and seed pelleting method). Here, the combination can be applied diluted or undiluted.

The term "seed" includes all types of seeds such as grains, seeds, fruits, tubers, seedlings and similar forms. Here, preferably the term "seed" refers to grains and seeds. The seeds used can be those of the crop plants mentioned above, but also of transgenic plants or plants obtained by conventional breeding methods.

When used for plant protection, the amount of active substance applied (i.e. compound of formula (I), component B and, if appropriate, component C), without formulation auxiliaries, depends on the type of effect desired. 0.001 to 2 kg per ha, preferably 0.005 to 2 kg per ha, more preferably 0.05 to 0.9 kg per ha, especially 0.1 to 0.75 kg per ha.

In another embodiment of the invention, the application rate of the compound of formula (I), component B and, if appropriate, component C is from 0.001 to 3 kg/ha of active substance (a.s.), preferably from 0.005 to 2.5 kg/ha. , and especially 0.01 to 2 kg/ha.

In another preferred embodiment of the invention, the application rate of the compound of formula (I) according to the invention (total amount of compound of formula (I)) is 0.1 g, depending on the control target, season, target plant and growth stage. /ha to 3000g/ha, preferably 10g/ha to 1000g/ha.

In another preferred embodiment of the invention, the application rate of the compound of formula (I) ranges from 0.1 g/ha to 5000 g/ha, also preferably from 1 g/ha to 2500 g/ha, or from 5 g/ha to 2000 g/ha. It is in the range of ha.

In another preferred embodiment of the invention, the application rate of the compound of formula (I) is between 0.1 and 1000 g/ha, preferably between 1 and 750 g/ha, more preferably between 5 and 500 g/ha.

The required application rate of herbicidal compound B generally ranges from 0.0005 kg/ha to 2.5 kg/ha of active substance (a.s.), preferably from 0.005 kg/ha to 2 kg/ha, or from 0.01 kg/ha to 1.5 kg. /ha range.

The required application rate of safener C generally ranges from 0.0005 kg/ha to 2.5 kg/ha of active substance (a.s.), preferably from 0.005 kg/ha to 2 kg/ha, or from 0.01 kg/ha. The range is 1.5kg/ha.

In the treatment of plant propagation material (e.g. seeds), for example by dusting, coating or drenching, from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g per 100 kg of plant propagation material (preferably seeds); Also most preferably amounts of active substance from 5 to 100 g are generally required.

In another embodiment of the invention, to treat seeds, the amount of active substance applied (i.e. the compound of formula (I), component B and, if appropriate, component C) is generally It is used in amounts of 0.001 to 10 kg per 100 kg.

When used for the protection of materials or stored products, the amount of active substance applied is determined depending on the type of application area and the desired effect. The amounts customarily applied in the protection of materials are from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg of active substance per cubic meter of material to be treated.

In the case of the combinations according to the invention, it is immaterial whether the compound of formula (I) and the further components B and/or C are applied in a joint formulation or in separate formulations.

In the case of individual applications, the order in which the applications are carried out is less important. The compound of formula (I) and the further components B and/or component C are applied in a time frame that allows simultaneous action of the active ingredients on the plant (preferably within a time frame of up to 14 days, in particular up to 7 days). All that is required is that the

Depending on the method of application, the compounds of formula (I), or formulations and/or combinations containing them, can additionally be used to eliminate undesirable vegetation in a further large number of crop plants. Examples of suitable crops are:
Onion (Allium cepa), pineapple (Ananas comosus), peanut (Arachis hypogaea), asparagus (Asparagus officinalis), Avena sativa, sugar beet altissima (Beta vulgaris spec. altissima), sugar beet rapa ( Beta vulgaris spec. rapa), Brassica napus var. napus, Rutabaga (Brassica napus var. napobrassica), Brassica rapa var. silvestris, Brassica oleracea oleracea), Brassica nigra, Tea tree (Camellia sinensis), Safflower (Carthamus tinctorius), Pecan (Carya illinoinensis), Lemon (Citrus limon), Orange (Citrus sinensis), Coffea arabica (Coffea canephora) ), Coffea liberica), cucumber (Cucumis sativus), Cynodon dactylon, carrot (Daucus carota), Guinea oil palm (Elaeis guineensis), Fragaria vesca, soybean (Glycine max), cotton ( Gossypium hirsutum), (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), sunflower (Helianthus annuus), Hevea brasiliensis, barley (Hordeum vulgare), hop (Humulus lupulus), sweet potato ( Ipomoea batatas), Linus regia (Juglans regia), Lens culinaris, Linum usitatissimum, Tomato (Lycopersicon lycopersicum), Malus spec., Cassava (Manihot esculenta), Alfalfa (Medicago sativa), Musa spec., tobacco (Nicotiana tabacum) (N. rustica), olive (Olea europaea), rice (Oryza sativa), lima bean (Phaseolus lunatus), kidney bean (Phaseolus vulgaris), Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pear ( Pyrus communis), apricot (Prunus armeniaca), sour cherry (Prunus cerasus), almond (Prunus dulcis) and plum (prunus domestica), currant (Ribes sylvestre), castor bean (Ricinus communis), sugarcane (Saccharum officinarum), rye (Secale) cereale), white mustard (Sinapis alba), potato (Solanum tuberosum), sorghum (sorghum bicolor), cacao (Theobroma cacao), red clover (Trifolium pratense), wheat (Triticum aestivum), triticale ( Tri ticale), durum wheat (Triticum durum), fava beans (Vicia faba), grapes (Vitis vinifera), and corn (Zea mays).

Preferred crops are peanuts (Arachis hypogaea), sugar beet Beta vulgaris spec. altissima, Brassica napus var. napus, Brassica oleracea, lemon (Citrus limon), Orange (Citrus sinensis), Coffee tree (Coffea arabica) (Coffea canephora, Coffea liberica), Cynodon dactylon, Soybean (Glycine max), Cotton (Gossypium hirsutum) (Gossypium arboreum) , Gossypium herbaceum, Gossypium vitifolium), sunflower (Helianthus annuus), barley (Hordeum vulgare), linden walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), Malus spec., alfalfa (Medicago sativa), tobacco (Nicotiana tabacum) (N. rustica), olive (Olea europaea), rice (Oryza sativa), lima bean (Phaseolus lunatus), Common beans (Phaseolus vulgaris), Pistacia vera (Pistacia vera), peas (Pisum sativum), almonds (Prunus dulcis), sugar cane (Saccharum officinarum), rye (Secale cereale), potato (Solanum tuberosum), sorghum (Sorghum bicolor) (sorghum (s. vulgare)), triticale (Triticale), wheat (Triticum aestivum), durum wheat (Triticum durum), faba bean (Vicia faba), grape (Vitis vinifera) and corn (Zea mays).

Particularly preferred crops are those of cereals, corn, soybeans, rice, rapeseed, cotton, potatoes, peanuts or orchard crops.

The compounds of formula (I) or the formulations and/or combinations containing them according to the invention may be modified by mutagenesis or genetic engineering in order to provide new traits to plants or to modify already existing traits. It can also be used in cultivated crops.

The term "crop" as used herein also refers to (crop) plants that have been modified by mutagenesis or genetic engineering to provide the plant with new traits or to modify already existing traits. include.

Mutagenesis is a technique of random mutagenesis using X-rays or mutagenic chemicals, as well as targeted mutagenesis to create mutations at specific loci in the plant genome. Also includes techniques. Targeted mutagenesis techniques often use oligonucleotides or proteins such as CRISPR/Cas, zinc finger nucleases, TALENs or meganucleases to achieve targeted effects.

Genetic engineering typically uses recombinant DNA technology to create modifications in plant genomes that cannot be easily obtained by cross-breeding, mutagenesis, or natural recombination in the natural environment. Typically, one or more genes are integrated into the genome of a plant to add or improve a trait. These integrated genes are also referred to as transgenes in the art, and plants containing such transgenes are referred to as transgenic plants. The process of plant transformation usually generates several transformation events that differ in the genomic locus into which the transgene is integrated. Plants containing a particular transgene on a particular genomic locus are usually described as containing a particular "event" referred to by the particular event name. Traits introduced or modified in plants include herbicide tolerance, insect resistance, increased yield, and tolerance to abiotic conditions such as drought, among others.

Herbicide resistance has been created using mutagenesis as well as using genetic engineering. Plants made resistant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding include plant varieties commercially available under the name Clearfield®. However, the majority of herbicide resistance traits have been created through the use of transgenes.

Herbicide tolerance includes glyphosate, glufosinate, 2,4-D, oxynyl herbicides such as dicamba, bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides, and 4-D herbicides such as isoxaflutole and mesotrione. It is designed for hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors.

Transgenes used to provide herbicide tolerance traits included: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for tolerance to glufosinate: pat and bar, Tolerance to 2,4-D: aad-1 and aad-12, Tolerance to dicamba: dmo, Tolerance to oxynyl herbicides: bxn, Tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm -hra, S4-HrA, for resistance to ALS inhibitor herbicides: csr1-2, for resistance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.

Transgenic maize events containing herbicide resistance genes include, for example, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO-01981-5( 0 here is expressed as O with a stroke in the original text), 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275, but do not exclude others.

Transgenic soybean events containing herbicide resistance genes are e.g. 6, DAS68416-4, DAS-81419-2, GU262, SYHT0H2 (0 here is written as O with a stroke in the original text), W62, W98, FG72, and CV127, but does not exclude others.

Transgenic cotton events containing herbicide resistance genes include, for example, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40, without excluding others.

Transgenic canola events containing herbicide resistance genes are, for example, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3, but excluding others. do not.

Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins into plants. The most frequently used transgenes are the toxin genes of Bacillus spec. and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, genes of plant origin have also been transferred into other plants, in particular genes encoding protease inhibitors, such as CpTI and pinII. A further approach uses transgenes to generate double-stranded RNA that targets and downregulates insect genes in plants. An example for such a transgene is dvsnf7.

Transgenic maize events containing genes for insecticidal proteins or double-stranded RNA are e.g. , TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098, without excluding others.

Transgenic soybean events containing genes for insecticidal proteins include, but are not exclusive of, MON87701, MON87751 and DAS-81419.

Transgenic cotton events containing genes for insecticidal proteins include, for example, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS9124, 281-24-236, 3006-210-23, GHB119 and SGK321, but do not exclude others.

Increased yields are produced by increasing panicle biomass using transgene athb17, present in maize event MON87403, or by promoting photosynthesis using transgene bbx32, present in soybean event MON87712. There is.

Crops containing modified oil content have been created by using the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events containing at least one of these genes are: 260-05, MON87705 and MON87769.

Tolerance to abiotic conditions, particularly drought, was achieved by using the transgene cspB contained in maize event MON87460 and soybean event IND-00410-5 (where the three 0s are It is produced by using the transgene Hahb-4 contained in

Traits are often combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combinations of traits include herbicide tolerance to herbicides of different groups, insect tolerance to different types of insects, especially tolerance to insects of the orders Lepidoptera and Coleoptera, herbicide tolerance and insect resistance of one or several types. , a combination of herbicide tolerance and increased yield, and herbicide tolerance and tolerance to abiotic conditions.

Plants containing single or stacked traits and the genes and events that provide these traits are well known in the art. For example, detailed information about mutagenized or integrated genes and the respective events can be found at the organization "International Service for the Acquisition of Agri-biotech Applications (ISAAA)" (http://www.isaaa.org/gmapprovaldatabase ) and the websites of the Center for Environmental Risk Assessment (CERA) (http://cera-gmc.org/GMCropDatabase), as well as patent applications such as EP3028573 and WO2017/011288.

The use of compounds of formula (I) or formulations or combinations containing them according to the invention on crop plants may result in specific effects on crops containing certain genes or events. These effects may be accompanied by changes in growth behavior or resistance to biotic or abiotic stress factors. Such effects include, inter alia, promotion of yield, promotion of resistance or resistance to insect, nematode, fungal, bacterial, mycoplasma, viral or viroid pathogens, and early vigor, It may include changes in early or delayed ripening, cold or heat tolerance, and amino acid or fatty acid spectrum or content.

Furthermore, through the use of recombinant DNA technology, plants containing modified amounts of ingredients or new ingredients, such as potatoes with increased production of amylopectin (e.g. Amflora (Reg. Trademark) Potato, BASF SE, Germany) is also included.

Furthermore, the compounds of formula (I) according to the invention or the formulations and/or combinations containing them can be used for defoliation and/or drying of plant parts of crops, such as cotton, potato, rape, sunflower, soybean or broad bean, in particular cotton. It has also been found that it is suitable for In this regard, formulations and/or combinations for drying and/or defoliation of crops, processes for preparing these formulations and/or combinations, and the use of compounds of formula (I) to dry plants and/or a method has been found for defoliating the leaves.

As desiccants, the compounds of formula (I) are particularly suitable for drying not only the above-ground parts of crop plants such as potatoes, oilseed rape, sunflowers and soybeans, but also the above-ground parts of cereals. This allows fully mechanical harvesting of these important crop plants.

Also of economic benefit is the ease of harvesting, which is important for citrus fruits, olives and other species, as well as for a variety of pernicious fruits, stone fruits and nuts, which can be dehisced or set on the tree. This is possible by concentrating the reduction within a specific period. The same mechanism, ie, promotion of the development of abscission tissue between the fruit or leaf part and the shoot part of the plant, is also essential for the control of defoliation in useful plants, especially cotton.

Furthermore, a reduction in the time interval between maturation of individual cotton plants leads to improved post-harvest fiber quality.

A Chemical Examples Chemical bonds depicted as bars in chemical formulas indicate relative stereochemistry on the ring system.

Example
[Example 1]
Synthesis of methyl(3S)-3-[[3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dioxazole-5-carbonyl]amino]butanoate (Cpd. I3)

step 1:

(1Z)-3,5-dichloro-N-hydroxy-benzimidoyl chloride (CAS677727-73-0; 3 g, 13.33 mmol) and methyl 3,3,3-trifluoro-2-oxo in toluene (50 ml). To a mixture of -propanoate (10.4g, 66.66mmol) triethylamine (1.36g, 13.33mmol) in toluene (20ml) was added dropwise at 25°C and the mixture was stirred at 25°C for 5 hours. The mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried, and concentrated. The crude material was purified by column chromatography (petroleum ether:ethyl acetate = 100:1 to 10:1) to give methyl 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4, 2-dioxazole-5-carboxylate (3.6 g, 82%) was obtained as a yellow oil. ¹ H NMR (400 MHz, CDCl3): δ 7.73 (d, J=1.88 Hz, 2H) 7.57 (t, J=1.82 Hz, 1H) 3.99 (s, 3H)

Step 2:
Methyl 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dioxazole-5-carboxylate (1 g, 3.31 mmol) in THF/H ₂ O (12 ml/4 ml) To the mixture was added lithium hydroxide (278 mg, 6.62 mmol) at 25°C, and the mixture was stirred at 25°C for 2 hours. The mixture was poured into water, the pH was adjusted to pH=3 and extracted with ethyl acetate. The combined organic layers were washed with brine, dried, and concentrated. Purification by preparative HPLC (trifluoroacetic acid, acetonitrile-water) produced 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dioxazole-5-carboxylic acid (700 mg, 64%) was obtained as a white solid. ¹ H NMR (400 MHz, CDCl3): δ 7.94 (t, J=1.82 Hz, 1H) 7.73 (d, J =1.88 Hz, 2H)

Step 3:
A mixture of 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dioxazole-5-carboxylic acid (1.1 g, 3.37 mmol) in dichloromethane (20 ml) was added with dimethylformamide. (1 drop) and (COCl) ₂ (641.35 mg, 5.05 mmol) were added at 25°C. The mixture was stirred at 25°C for 1 hour. The mixture was concentrated, dissolved in dichloromethane (5 mL) and added dropwise to methyl (3S)-3-aminobutanoate hydrochloride (834 mg, 5.05 mmol) in pyridine (22 ml) at 0°C. The resulting mixture was stirred at 25°C for 2 hours. The mixture was poured into water and extracted with ethyl acetate. The combined organics were washed with brine, dried, and concentrated. Purification by preparative HPLC (trifluoroacetic acid, acetonitrile-water) revealed methyl(3S)-3-[[3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-di Oxazole-5-carbonyl]amino]butanoate (130 mg, 9%) was obtained as a white solid. ¹ H NMR (400 MHz, CDCl3): δ 7.75 (t, J = 1.7 Hz, 2H), 7.57 (s, 1H), 7.52 - 7.40 (m, 1H), 4.49 - 4.34 (m, 1H), 3.75 - 3.69 (m, 3H), 2.69 - 2.53 (m, 2H), 1.35 - 1.30 (m, 3H)

High performance liquid chromatography: HPLC-column Kinetex flow gradient from 0.8 ml/min to 1.0 ml/min in 1.5 min).

Similar to the examples described above, the following compounds of formula (I) where R ¹ is hydrogen were prepared starting from commercially available diesters and using commercially available amines:

B Use Examples The herbicidal activity of compounds of formula (I) was demonstrated by the following greenhouse experiments:

The culture container used was a plastic flower pot containing loam sand containing approximately 3.0% corrosive material as the culture medium. Seeds of test plants were sown separately for each species.

For pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using a dispensing nozzle. The containers were watered gently to promote germination and growth and then covered with a clear plastic hood until the test plants were established. This cover resulted in uniform germination of the test plants, as long as it was not impaired by the active ingredient.

For post-emergence treatments, the test plants were first grown to a height of 3 to 15 cm, depending on their habitat, and only then treated with the active ingredient suspended or emulsified in water. For this purpose, the test plants were either directly sown and grown in the same container, or these test plants were first grown separately as seedlings and transplanted into the test containers a few days before treatment.

The test plants were kept at 10-25°C or 20-35°C, respectively, depending on the species.

The study period ranged from 2 to 4 weeks. During this period, the test plants were cared for and evaluated for their response to the individual treatments.

Evaluations were made using a scale of 0 to 100. 100 means no emergence or at least complete destruction of the aerial part of the test plants, 0 means no damage or normal growth process. Good herbicidal activity is indicated by a value of 80-90, and very good herbicidal activity is indicated by a value of 90-100.

The test plants used in the greenhouse experiments were the following species:

Applied by pre-emergence method at an application rate of 1.000 kg/ha:
- Compounds I7, I8, and I10 showed very good herbicidal activity against APESV.
- Compound I8 showed very good herbicidal activity against AMARE.
- Compound I10 showed good herbicidal activity against AMARE.
- Compounds I8 and I10 showed very good herbicidal activity against ECHCG.
- Compound I7 showed good herbicidal activity against ECHCG.
- Compound I7 showed very good herbicidal activity against SETFA.

Applied by pre-emergence method at an application rate of 0.500 kg/ha:
- Compound I3 showed very good herbicidal activity against AMARE.
- Compound I2 showed good herbicidal activity against APESV.
- Compounds I1, I3, I4, I5, and I6 showed very good herbicidal activity against APESV.
- Compounds I1, I4, I5, and I6 showed very good herbicidal activity against ECHCG.

Applied by pre-emergence method at an application rate of 0.250 kg/ha:
- Compounds I9 and I11 showed very good herbicidal activity against APESV.
- Compounds I9 and I11 showed good herbicidal activity against AMARE.
- Compound I11 showed very good herbicidal activity against ECHCG.

Applied by post-emergence method at an application rate of 1.000 kg/ha:
- Compounds I7, I8, and I10 showed very good herbicidal activity against ECHCG.
- Compounds I7 and I8 showed very good herbicidal activity against AMARE.
- Compound I10 showed good herbicidal activity against AMARE.
- Compounds I7, I8, and I10 showed very good herbicidal activity against SETVI.

Applied by post-emergence method at an application rate of 0.500 kg/ha:
- Compounds I1, I2, I4, I5, and I6 showed very good herbicidal activity against ALOMY.
・Compound I3 showed good herbicidal activity against ALOMY.
- Compounds I3, I4, I5, and I6 showed very good herbicidal activity against AVEFA.
- Compound I2 showed good herbicidal activity against AVEFA.
- Compound I1 showed very good herbicidal activity against ECHCG.
- Compound I6 showed very good herbicidal activity against SETVI.
- Compounds I1, I2, I3, I4, and I5 showed good herbicidal activity against SETVI.

Applied by post-emergence method at an application rate of 0.250 kg/ha:
・Compounds I9 and I11 showed very good herbicidal activity against ALOMY.
- Compound I9 showed very good herbicidal activity against AVEFA.
- Compound I11 showed very good herbicidal activity against ECHCG.
- Compounds I9 and I11 showed very good herbicidal activity against SETVI.
Aspects of the present disclosure include the following.
[1]
Formula (I)
[wherein the substituents have the following meanings:
R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-Haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, ( C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy;
R ² is hydrogen, halogen, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )- is haloalkoxy;
R ³ is hydrogen, halogen, nitro, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, hydroxy-(C ₁ -C ₃ )-alkyl, (C ₃ - C5 ₎ -cycloalkyl, (C3 _- C5 ₎ -halocycloalkyl, hydroxy-( _C3 - _C5 )-cycloalkyl, (C1 _- C3 ₎ -alkoxy, (C1 _- C3 ₎ - Haloalkoxy, (C ₁ -C ₃ )-alkoxycarbonyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl;
R4 is hydrogen, halogen, hydroxyl, cyano, (C1 _- C3 ₎ -alkyl, (C1 ^- _C3 ) _-haloalkyl , (C3 _- C4 ₎ -halocycloalkyl, (C1 _- C3 ₎ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkylthio;
R ⁵ is hydrogen, halogen, nitro, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, hydroxy-(C ₁ -C ₃ )-alkyl, (C ₃ - C5 ₎ -cycloalkyl, (C3 _- C5 ₎ -halocycloalkyl, hydroxy-( _C3 - _C5 )-cycloalkyl, (C1 _- C3 ₎ -alkoxy, (C1 _- C3 ₎ - Haloalkoxy, (C ₁ -C ₃ )-alkoxycarbonyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl;
R ⁶ is hydrogen, halogen, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )- is haloalkoxy;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond (X ⁰ ), or (X ¹ ), (X ² ), (X ³ ), (X ⁴ ), (X ⁵ ) and (X ⁶ ):
is a divalent unit from the group consisting of;
R ⁸ to R ¹³ are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO ₂ R ^e , CONR ^b R ^d , NR ^b CO ₂ R ^e , R ^a , or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₅ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl (respectively, fluorine, chlorine, bromine, iodine, hydroxyl and cyano), or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-alkenyloxy , (C ₃ -C ₆ )-alkynyloxy, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl (respectively, fluorine, chlorine , bromine, iodine, cyano and (C ₁ -C ₂ )-alkoxy);
Y is hydrogen, cyano, hydroxyl, Z,
or
(C ₁ -C ₁₂ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₁₂ )-alkenyl or (C ₂ -C ₁₂ )-alkynyl, each of which represents fluorine, chlorine, Bromine, iodine, cyano, hydroxyl, OR ^d , Z, OZ, NHZ, S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , CO ₂ R ^e , CONR ^b R ^h , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e , NR ^b SO ₂ NR ^b R ^e , OCONR substituted by m groups from the group consisting of ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e ;
Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and CO ₂ R ^e , CONR ^b R ^h , S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b From SO ₂ R ^e , NR ^b SO ₂ NR ^b R ^e , OCONR ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e , R ^b , R ^c , R ^e and R ^f a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring (other than phenyl) substituted by m groups from the group consisting of , has n oxo groups;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which represents fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C ₁ -C 6 )-cycloalkyl . substituted by m groups selected from the group consisting of ₃ )-alkoxy;
R ^b is hydrogen, (C ₁ -C ₃ )-alkoxy, or R ^a ;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^d is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₃ -C ₆ )-cycloalkyl-( C1 _- C3 ) _-alkyl , phenyl-(C1 _- C3 ₎ -alkyl, furanyl-(C1 _- C3 ₎ -alkyl or (C2 _- C4 ₎ -alkynyl, each of which is Fluorine, chlorine, bromine, cyano, CO ₂ R ^a , CONR ^b R ^h , (C ₁ -C ₂ )-alkoxy, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, ( substituted by m groups selected from the group consisting of C ₁ -C ₃ )-alkylsulfonyl, phenylthio, phenylsulfinyl and phenylsulfonyl;
R ^e is R ^d ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₂ )-alkoxy, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-Alkoxycarbonyl-(C ₁ -C ₆ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which represents fluorine, chlorine, bromine, cyano, CO ₂ R ^a , and substituted by m groups selected from the group consisting of (C ₁ -C ₂ )-alkoxy;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1 or 2;
r is 1, 2, 3, 4, 5 or 6]
5-methyl-3-phenyl-1,4, A compound of formula (I), excluding 2-dioxazole-5-carboxamide.
[2]
The substituents have the following meanings:
R ¹ is hydrogen
A compound according to embodiment 1.
[3]
The substituents have the following meanings:
R ² is hydrogen, halogen, (C ₁ -C ₃ )-alkyl;
R ⁶ is hydrogen, halogen, (C ₁ -C ₃ )-alkyl
A compound according to embodiment 1 or 2.
[4]
The substituents have the following meanings:
R ³ is hydrogen, halogen, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl;
R ⁵ is hydrogen, halogen, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl
A compound according to any one of embodiments 1 to 3.
[5]
The substituents have the following meanings:
R ⁴ is hydrogen, halogen
A compound according to any one of embodiments 1 to 4.
[6]
The substituents have the following meanings:
R ⁷ is (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₁ -C ₃ )-alkoxy, each of which is substituted by m groups from the group consisting of fluorine, chlorine, and (C ₁ -C ₂ )-alkoxy
A compound according to any one of embodiments 1 to 5.
[7]
The substituents have the following meanings:
R ⁷ is (C ₁ -C ₂ )-alkyl, cyclopropyl, (C ₁ -C ₂ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₁ -C ₂ )-alkoxy
A compound according to any one of embodiments 1 to 5.
[8]
The substituents have the following meanings:
X is a bond
A compound according to any one of embodiments 1 to 7.
[9]
The substituents have the following meanings:
X is a bond;
Y is (C ₁ -C ₈ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₈ )-alkenyl or (C ₂ -C ₈ )-alkynyl, each of which has fluorine , chlorine, bromine, iodine, cyano, hydroxyl, OR ^d , Z, OZ, NHZ, S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , CO ₂ R ^e , CONR ^b R ^h , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e NR ^b SO ₂ NR ^b R ^e , OCONR ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )= NOR ^e
9. A compound according to any one of embodiments 1 to 8.
[10]
The substituents have the following meanings:
X is a bond;
Y is Z;
Z is a 4- or 5-membered saturated or partially unsaturated ring formed from r carbon atoms and n oxygen atoms, respectively, CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ substituted by m groups from the group consisting of R ^a , R ^b , R ^c , R ^e and R ^f
9. A compound according to any one of embodiments 1 to 8.
[11]
The substituents have the following meanings:
R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-Haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, ( C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy;
R ² is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
R3 is hydrogen, halogen, hydroxyl, cyano, (C1 _- C3 ₎ -alkyl, (C1 ^- _C3 ) _-haloalkyl , (C3 _- C5 ₎ -halocycloalkyl, (C1 _- C3 ₎ )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
R4 is hydrogen, halogen, hydroxyl, cyano, (C1 _- C3 ₎ -alkyl, (C1 ^- _C3 ) _-haloalkyl , (C3 _- C4 ₎ -halocycloalkyl, (C1 _- C3 ₎ )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
R5 is hydrogen, halogen, hydroxyl, cyano, (C1 _- C3 ₎ -alkyl, (C1 ^- _C3 ) _-haloalkyl , (C3 _- C5 ₎ -halocycloalkyl, (C1 _- C3 ₎ )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
R ⁶ is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
R ⁷ is (C ₁ -C ₂ )-alkyl, cyclopropyl, (C ₁ -C ₂ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₁ -C ₂ )-alkoxy;
X is a bond;
Y is Z or (C ₁ -C ₈ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₈ )-alkenyl or (C ₂ -C ₈ )-alkynyl, respectively is substituted by m groups from the group consisting of fluorine, CO ₂ R ^e and CONR ^e SO ₂ R ^a ;
Z is formed from r carbon atoms, n oxygen atoms, and consists of CO 2 R _e , ^CONR b ^R h ^, CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f a 4- to 5-membered saturated or partially unsaturated ring substituted by m groups from the group;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by m groups;
R ^b is hydrogen or (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by selected m groups;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-alkoxycarbonyl-( C1 _- C6 )-alkyl or (C2 _- C4 ₎ -alkynyl, each selected from the group consisting of fluorine, chlorine, bromine, cyano _and ( _C1 - _C2 )-alkoxy substituted by m groups;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1 or 2;
r is 1, 2, 3, 4 or 5
A compound according to embodiment 1.
[12]
12. A composition comprising at least one compound according to any one of embodiments 1 to 11 and at least one auxiliary agent customary for the formulation of crop protection compounds.
[13]
13. A composition according to embodiment 12, comprising a further herbicide.
[14]
13. Use of a compound according to any one of embodiments 1 to 11 or a composition according to embodiments 12 or 13 for controlling unwanted vegetation.
[15]
A herbicidally effective amount of at least one compound according to any one of embodiments 1 to 11 or the composition according to embodiments 12 or 13 is applied to plants, their seeds and/or their habitats. methods for controlling unwanted vegetation, including;

Claims (15)

Formula (I)
[wherein the substituents have the following meanings:
R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-Haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, ( C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy;
R ² is hydrogen, halogen, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )- is haloalkoxy;
R ³ is hydrogen, halogen, nitro, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, hydroxy-(C ₁ -C ₃ )-alkyl, (C ₃ - _C5 )-cycloalkyl, ( _C3 - _C5 )-halocycloalkyl, hydroxy-( _C3 - _C5 )-cycloalkyl, (C1 _{- C3} )-alkoxy, ( _C1 - _C3 )- Haloalkoxy, (C ₁ -C ₃ )-alkoxycarbonyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl;
^R4 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C4 )-halocycloalkyl, ( _C1 - _C3) )-alkoxy , (C ₁ -C ₃ )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkylthio;
R ⁵ is hydrogen, halogen, nitro, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, hydroxy-(C ₁ -C ₃ )-alkyl, (C ₃ - _C5 )-cycloalkyl, ( _C3 - _C5 )-halocycloalkyl, hydroxy-( _C3 - _C5 )-cycloalkyl, (C1 _{- C3} )-alkoxy, ( _C1 - _C3 )- Haloalkoxy, (C ₁ -C ₃ )-alkoxycarbonyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl;
R ⁶ is hydrogen, halogen, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )- is haloalkoxy;
R ⁷ is fluorine, cyano, or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₁ -C ₆ )-alkoxy, each substituted by m groups from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano, and (C ₁ -C ₆ )-alkoxy) And;
X is a bond (X ⁰ ), or (X ¹ ), (X ² ), (X ³ ), (X ⁴ ), (X ⁵ ) and (X ⁶ ):
is a divalent unit from the group consisting of;
R ⁸ to R ¹³ are each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO ₂ R ^e , CONR ^b R ^d , NR ^b CO ₂ R ^e , R ^a , or (C ₁ -C ₆ )-alkyl, (C ₃ -C ₅ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl (respectively, fluorine, chlorine, bromine, iodine, hydroxyl and cyano), or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-alkenyloxy , (C ₃ -C ₆ )-alkynyloxy, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, (C ₁ -C ₃ )-alkylsulfonyl (respectively, fluorine, chlorine , bromine, iodine, cyano and (C ₁ -C ₂ )-alkoxy);
Y is hydrogen, cyano, hydroxyl, Z,
or
(C ₁ -C ₁₂ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₁₂ )-alkenyl or (C ₂ -C ₁₂ )-alkynyl, each of which represents fluorine, chlorine, Bromine, iodine, cyano, hydroxyl, OR ^d , Z, OZ, NHZ, S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , CO ₂ R ^e , CONR ^b R ^h , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e , NR ^b SO ₂ NR ^b R ^e , OCONR substituted by m groups from the group consisting of ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e ;
Z is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and CO ₂ R ^e , CONR ^b R ^h , S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b From SO ₂ R ^e , NR ^b SO ₂ NR ^b R ^e , OCONR ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e , R ^b , R ^c , R ^e and R ^f a 3-, 4-, 5- or 6-membered saturated, partially unsaturated, fully unsaturated or aromatic ring (other than phenyl) substituted by m groups from the group consisting of , has n oxo groups;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which represents fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C ₁ -C 6 )-cycloalkyl. substituted by m groups selected from the group consisting of ₃ )-alkoxy;
R ^b is hydrogen, (C ₁ -C ₃ )-alkoxy, or R ^a ;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^d is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₃ -C ₆ )-cycloalkyl-( _C1 - _C3 )-alkyl, phenyl-( _C1 - _C3 )-alkyl, furanyl-( _C1 - _C3 )-alkyl or ( _C2 - _C4 )-alkynyl, each of which is Fluorine, chlorine, bromine, cyano, CO ₂ R ^a , CONR ^b R ^h , (C ₁ -C ₂ )-alkoxy, (C ₁ -C ₃ )-alkylthio, (C ₁ -C ₃ )-alkylsulfinyl, ( substituted by m groups selected from the group consisting of C ₁ -C ₃ )-alkylsulfonyl, phenylthio, phenylsulfinyl and phenylsulfonyl;
R ^e is R ^d ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₂ )-alkoxy, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-Alkoxycarbonyl-(C ₁ -C ₆ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which represents fluorine, chlorine, bromine, cyano, CO ₂ R ^a , and substituted by m groups selected from the group consisting of (C ₁ -C ₂ )-alkoxy;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1 or 2;
r is 1, 2, 3, 4, 5 or 6]
5 -methyl-3-phenyl - 1,4, A compound of formula (I), excluding 2-dioxazole-5-carboxamide. The substituents have the following meanings:
2. A compound according to claim 1, wherein R ¹ is hydrogen. The substituents have the following meanings:
R ² is hydrogen, halogen, (C ₁ -C ₃ )-alkyl;
3. The compound according to claim 1 or 2, wherein R ⁶ is hydrogen, halogen, or (C ₁ -C ₃ )-alkyl. The substituents have the following meanings:
R ³ is hydrogen, halogen, hydroxyl, cyano, (C ₁ -C ₃ )-alkyl;
4. A compound according to any one of claims 1 to 3, wherein ^R5 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl. The substituents have the following meanings:
5. The compound according to claim 1, wherein R ⁴ is hydrogen or halogen. The substituents have the following meanings:
R ⁷ is (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₁ -C ₃ )-alkoxy, each of which is 6. A compound according to any one of claims 1 to 5, substituted by m groups from the group consisting of fluorine, chlorine, and ( _C1 - _C2 )-alkoxy. The substituents have the following meanings:
A claim in which R ⁷ is (C ₁ -C ₂ )-alkyl, cyclopropyl, (C ₁ -C ₂ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₁ -C ₂ )-alkoxy. A compound according to any one of 1 to 5. The substituents have the following meanings:
8. A compound according to any one of claims 1 to 7, wherein X is a bond. The substituents have the following meanings:
X is a bond;
Y is (C ₁ -C ₈ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₈ )-alkenyl or (C ₂ -C ₈ )-alkynyl, each of which has fluorine , chlorine, bromine, iodine, cyano, hydroxyl, OR ^d , Z, OZ, NHZ, S(O) _n R ^a , SO ₂ NR ^b R ^d , SO ₂ NR ^b COR ^e , CO ₂ R ^e , CONR ^b R ^h , COR ^b , CONR ^e SO ₂ R ^a , NR ^b R ^e , NR ^b COR ^e , NR ^b CONR ^e R ^e , NR ^b CO ₂ R ^e , NR ^b SO ₂ R ^e NR ^b SO ₂ NR ^b R ^e , OCONR ^b R ^e , OCSNR ^b R ^e , POR ^f R ^f and C(R ^b )=NOR ^e , according to any one of claims 1 to 8. compound. The substituents have the following meanings:
X is a bond;
Y is Z;
Z is a 4- or 5-membered saturated or partially unsaturated ring formed from r carbon atoms and n oxygen atoms, respectively, CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ 9. A compound according to any one of claims 1 to 8, substituted by m groups from the group consisting of R ^a , R ^b , R ^c , R ^e and R ^f . The substituents have the following meanings:
R ¹ is hydrogen, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₄ )-cycloalkyl, (C ₁ -C ₃ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₂ -C ₃ )-Haloalkenyl, (C ₂ -C ₃ )-alkynyl, (C ₂ -C ₃ )-haloalkynyl, (C ₁ -C ₃ )-alkoxy-(C ₁ -C ₃ )-alkyl, ( C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy;
R ² is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
^R3 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C5 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R4 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C4 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
^R5 is hydrogen, halogen, hydroxyl, cyano, ( _C1 - _C3 )-alkyl, ( _C1 - _C3 )-haloalkyl, ( _C3 - _C5 )-halocycloalkyl, ( _C1 - _C3) )-haloalkoxy, (C ₂ -C ₃ )-haloalkenyl, (C ₂ -C ₃ )-haloalkynyl;
R ⁶ is hydrogen, halogen, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-haloalkyl, (C ₁ -C ₃ )-alkoxy, (C ₁ -C ₃ )-haloalkoxy; ;
R ⁷ is (C ₁ -C ₂ )-alkyl, cyclopropyl, (C ₁ -C ₂ )-haloalkyl, (C ₂ -C ₃ )-alkenyl, (C ₁ -C ₂ )-alkoxy;
X is a bond;
Y is Z or (C ₁ -C ₈ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₂ -C ₈ )-alkenyl or (C ₂ -C ₈ )-alkynyl, respectively is substituted by m groups from the group consisting of fluorine, CO ₂ R ^e and CONR ^e SO ₂ R ^a ;
Z is formed from r carbon atoms, n oxygen atoms, and consists of CO ₂ R ^e , CONR ^b R ^h , CONR ^e SO ₂ R ^a , R ^b , R ^c , R ^e and R ^f a 4- to 5-membered saturated or partially unsaturated ring substituted by m groups from the group;
R ^a is (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by m groups;
R ^b is hydrogen or (C ₁ -C ₆ )-alkyl or (C ₃ -C ₆ )-cycloalkyl, each of which is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy. substituted by selected m groups;
R ^c is fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) _n R ^a , or (C ₁ -C ₆ )-alkoxy, (C ₃ -C ₆ )-alkenyloxy or (C ₃ - C ₆ )-alkynyloxy, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy;
R ^e is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, phenyl-(C ₁ -C ₃ )-alkyl or (C ₂ -C ₄ )-alkynyl, each of which is substituted by m groups selected from the group consisting of fluorine, chlorine, bromine, cyano and (C ₁ -C ₂ )-alkoxy; ;
R ^f is (C ₁ -C ₃ )-alkyl or (C ₁ -C ₃ )-alkoxy;
R ^h is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₁ -C ₆ )-alkoxycarbonyl-( _C1 - _C6 )-alkyl or ( _C2 - _C4 )-alkynyl, each selected from the group consisting of fluorine, chlorine, bromine, cyano and ( _C1 - _C2 )-alkoxy substituted by m groups;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1 or 2;
2. The compound according to claim 1, wherein r is 1, 2, 3, 4 or 5. 12. A composition comprising at least one compound according to any one of claims 1 to 11 and at least one auxiliary agent customary for the formulation of crop protection compounds. 13. A composition according to claim 12, comprising a further herbicide. 14. Use of a compound according to any one of claims 1 to 11 or a composition according to claims 12 or 13 for controlling unwanted vegetation. Acting a herbicidally effective amount of at least one compound according to any one of claims 1 to 11 or a composition according to claims 12 or 13 on plants, their seeds and/or their habitat. A method for controlling unwanted vegetation, including: