WO2025026808A1

WO2025026808A1 - Herbicidal alanine analogues

Info

Publication number: WO2025026808A1
Application number: PCT/EP2024/070822
Authority: WO
Inventors: Markus Kordes; Marc Heinrich; Tobias SEISER; Gerd Kraemer; Trevor William Newton
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 2023-08-03
Filing date: 2024-07-23
Publication date: 2025-02-06
Anticipated expiration: 2026-02-03
Also published as: AR133458A1

Abstract

The present invention relates to Alanine analogues of the formula (I) (I) where the variables are as defined in the claims and the description, and to the use of said Alanine analogues for controlling unwanted vegetation, and to methods of applying the Alanine analogues.

Description

Herbicidal Alanine analogues

The present invention relates to specific Alanine analogues, and to the use of said Alanine analogues for controlling unwanted vegetation. Furthermore, the invention relates to methods of applying the Alanine analogues.

BACKGROUND OF THE INVENTION

For controlling unwanted vegetation, especially in crops, there is an ongoing need for new herbicides that have high activity and selectivity together with a substantial lack of toxicity for humans and animals.

WO2023/025855, WO2022/112347, and WO2023/025854 describe alkyl-substituted malonamide compounds and their use as herbicides.

The prior art compounds often suffer from insufficient herbicidal activity, in particular at low application rates, and/or unsatisfactory selectivity, resulting in a low compatibility with crop plants.

Certain N-(benzoyl)-alanine derivatives comprising a N-(benzoyl)-alanine derivative and a second amino acid moiety and processes for their preparation are for instance known from Saavedra, Carlos; Hernandez, Rosendo; Boto, Alicia; Alvarez, Eleuterio J. Org. Chem. 2009, 74, 4655-65. No biological activity, e.g. herbicidal activity, was reported for these compounds.

Accordingly, it is an object of the present invention to provide further herbicidal ly active compounds having a strong herbicidal activity, in particular even at low application rates, a sufficiently low toxicity for humans and animals and/or a high compatibility with crop plants. The compounds should also show a broad activity spectrum 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, stereoisomers and tautomers.

SUMMARY OF THE INVENTION

Accordingly, the present invention relates to compounds of formula (I)

wherein the substituents have the following meanings: R¹, R⁸ independently of each other are hydrogen, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (C3-C4)-cycloalkyl, (C2-C3)- alkenyl, (C2-C3)-haloalkenyl, (C3-C4)-alkynyl, (C3-C4)-haloalkynyl, (Ci-C3)-alkoxy-(Ci-C3)-alkyl, aryl, aryl-(Ci- C3)-alkyl, (Ci-C3)-alkoxy, (Ci-C3)-haloalkoxy, (Ci-C3)-alkoxy-(Ci-C3)-alkoxy, (Ci-C3)-alkylcarbonyl, arylcarbonyl, (Ci-C3)-alkoxycarbonyl, or aryloxycarbonyl;

R², R⁶ independently of each other are hydrogen, halogen, hydroxyl, cyano, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (C1- C3)-alkoxy or (Ci-C3)-haloalkoxy;

R³, R⁵ independently of each other are hydrogen, halogen, nitro, hydroxyl, cyano, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (Cs-CsJ-cycloalkyl, (Cs-CsJ-halocycloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C1-C3)- alkoxy, (Ci-C3)-haloalkoxy, (Ci-C3)-alkoxycarbonyl, (Ci-C3)-haloalkoxycarbonyl, (Ci-C3)-alkylthio, (C1-C3)- haloalkylthio, (Ci-C3)-alkylsulfinyl, (Ci-C3)-haloalkylsulfinyl, (Ci-C3)-alkylsulfonyl, (Ci-C3)-haloalkylsulfonyl, or (Ci-C3)-dialkylamino;

R⁴ is hydrogen, halogen, hydroxyl, cyano, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (C3-C4)-cycloalkyl, (C3-C4)- halocycloalkyl, (Ci-C3)-alkoxy, (Ci-CsJ-haloalkoxy, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C1- Csj-dialkylamino or (Ci-C3)-alkylthio;

R⁷ is methyl or ethyl;

R⁹ is hydrogen;

X is oxygen or sulfur;

Q represents the radical of formula (Z-Y),

wherein the arrow represents the bond to the adjacent nitrogen atom, and wherein the substituents have the following meanings

R¹⁰ is (Ci-C₄)-alkyl;

R¹¹, R¹², R¹³, R¹⁴ independently of each other are hydrogen or (Ci-C4)-alkyl; or

R¹⁰ and R¹⁴ form, together with the carbon atoms to which they are bound, a three- to six-membered saturated or partially unsaturated carbocycle or a three- to six-membered saturated or partially unsaturated heterocycle containing 1 or 2 oxygen, nitrogen or sulfur atoms as ring members

Y is CO₂R^e, CONR^bR^h, CONR^eS(O)R^a, CONR^eSO₂R^a, or CONR^b1SO₂NR^b2R^b3; each R^a is independently (Ci-Cej-alkyl, (Ci-Cej-haloalkyl, (C3-C4)-alkynyl or (Cs-Cej-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (Ci-Csj-alkoxy;

R^b is hydrogen or (Ci-Cej-alkyl, (C2-C4)-alkenyl, (C3-C4)-alkynyl, (Cs-Cej-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C3)- alkyl, phenyl-(Ci-C3)-alkyl or furanyl-(Ci-C3)-alkyl, where each of the seven last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkoxy, (Ci-Csj-alkylthio, (Ci-Csj-alkylsulfinyl, (Ci-Csj-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R^b1 and R^b2 independently of each other and independently of each occurrence, are hydrogen or have one of the meanings given for R^a;

R^b3 is hydrogen or (Ci-Ce)-alkyl, (C2-C4)-alkenyl, (C3-C4)-alkynyl, (Ca-CeJ-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C3)- alkyl, phenyl-(Ci-C3)-alkyl or furanyl-(Ci-C3)-alkyl, where each of the seven last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, , (Ci-C2)-alkoxy, (Ci-C3)-alkylthio, (Ci-C3)-alkylsulfinyl, (Ci-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; or

R^b2 and R^b3 form, together with the nitrogen atom to which they are bound, a saturated 3-, 4-, 5-, 6- or 7-membered N-bound heterocycle which may contain one further heteroatom or heteroatom group selected from the group consisting of N, 0, S, S(0) and S(0)2 as ring member; each R^e is independently hydrogen or (Ci-C6)-alkyl, (C2-C4)-alkenyl, (C3-C4)-alkynyl, (Ca-CeJ-cycloalkyl, (Cs-Ce)- cycloalkyl-(Ci-C3)-alkyl, phenyl-(Ci-C3)-alkyl or furanyl-(Ci-C3)-alkyl, where each of the seven last- mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkoxy, (Ci-C2)-haloalkoxy, (Ci-C3)-alkylthio, (Ci-C3)-haloalkylthio, (C1-C3)- alkylsulfinyl, (Ci-C3)-haloalkylsulfinyl, (Ci-C3)-alkylsulfonyl, (Ci-C3)-haloalkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

R^h is hydrogen or (Ci-CeJ-alkyl, (Ci-C2)-alkoxy, (Cs-CeJ-cycloalkyl, (C2-C4)-alkenyl, (Ci-C6)-alkoxycarbonyl- (Ci-C6)-alkyl, or (C3-C4)-alkynyl, where each of the six last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkyl, (Ci-C2)-alkoxy and (Ci-C2)-alkoxy-(Ci-C2)-alkoxy; or

R^b and R^h form, together with the nitrogen atom to which they are bound, a saturated 3-, 4-, 5-, 6- or 7- membered N-bound heterocycle which may contain one further heteroatom or heteroatom group selected from the group consisting of N, 0, S, S(0) and S(0)2 as ring member; m is independently of each occurrence 0, 1 , 2 or 3; n is 1 or 2; including their agriculturally acceptable salts, stereoisomers and tautomers; except for the following compounds:

• (1 R,3S)-3-[[2-[(3-Nitrobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid,

• (1R,3S)-3-[[2-[(2,3-Dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid,

• (1S,3R)-3-[[2-[(3-Nitrobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid,

• (1S,3R)-3-[[2-[(2,3-Dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid,

• 3-[[2-(Benzoylamino)-1-oxopropyl]amino]cyclopentanecarboxylic acid,

• 3-[[2-[(2,3-Dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid,

• 3-[[2-[(4-Bromobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid,

• 4-[[2-(Benzoylamino)-1-oxopropyl]amino]cyclohexanecarboxylic acid,

• 4-[[2-(Benzoylamino)-1-oxopropyl]amino]pentanoic acid,

• 4-[[2-[(2,3-Dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid,

• 4-[[2-[(2,3-Dichlorobenzoyl)amino]-1-oxopropyl]amino]pentanoic acid, • 4-[[2-[(2-Chlorobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid,

• 4-[[2-[(3-Nitrobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid,

• 4-[[2-[(3-Nitrobenzoyl)amino]-1-oxopropyl]amino]pentanoic acid,

• 4-[[2-[(4-Bromobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid,

• 4-[[2-[(4-Bromobenzoyl)amino]-1-oxopropyl]amino]pentanoic acid,

• 4-[[2-[(4-Chlorobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid,

• 4-[[2-[[4-(1 ,1-Dimethylethyl)benzoyl]amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid,

• cis-3-[[2-[(2,3-Dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclobutanecarboxylic acid,

• cis-3-[[2-[(3-Nitrobenzoyl)amino]-1-oxopropyl]amino]cyclobutanecarboxylic acid

• N-[1-Methyl-2-oxo-2-[[(1 S,3R)-3-(1-piperidinylcarbonyl)cyclopentyl]amino]ethyl]benzamide.

The invention also relates to a composition comprising at least one compound of formula (I) and at least one auxiliary which is customary for formulating crop protection compounds.

The present invention also provides combinations comprising at least one compound of formula (I) (component A) and safeners C (component C).

The invention relates moreover to the use of a compound of formula (I) for controlling unwanted vegetation, and to a method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one compound of formula (I) to act on plants, their seed and/or their habitat.

DETAILED DESCRIPTION OF THE INVENTION

Definitions:

Depending on the kind of substituents, the compounds of formula (I) may have one or more centers of chirality, in which case they may be present as mixtures of enantiomers or diastereomers but also in the form of the pure enantiomers or pure diastereomers. The invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula I or their mixtures. Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) as a specific form of diastereomers and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond, amide group or a cyclic, non-aromatic moiety. The term "stereoisomer(s)" encompasses both optical isomers, such as enantiomers or diastereomers existing due to more than one stereogenic center in the molecule, as well as geometrical isomers (cis/trans isomers). Just by way of example, a stereogenic center is the C atom carrying R⁷ and R⁹. If the above-mentioned safeners C have one or more centres of chirality they may also be present as enantiomers or diastereomers, and it is possible to use both the pure enantiomers and pure diastereomers or their mixtures.

If the compounds of formula (I), or the safeners C as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.

Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by C1-C4- alkyl, hydroxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, 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 salt), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium, and finally the salts of polybasic amines such as N,N-bis-(3- aminopropyl)methylamine and diethylenetriamine.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.

If the compounds of formula (I) can form tautomers due to intramolecular proton transfer, these tautomers are also encompassed by the definition and comprised by the scope of general formula (I) according to the invention. Common examples of such interconversions i.a. are keto-enol- (H-O-C=C O=C-C-H) and amide-imidic acid- (H-N-C=O N=C-O-H) tautomerism.

The amount in which the one or other tautomeric form is present depends on the complete molecular structure and even stronger on the surrounding conditions (presence or absence of solvent, type of solvent, pH, temperature etc.).

The term "undesired vegetation" ("weeds") is understood to include any vegetation growing in non-crop-areas or at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired crop (if any). Weeds, in the broadest sense, are plants considered undesirable in a particular location. The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix C_n-C_m indicates in each case the possible number of carbon atoms in the group.

The term "halogen" denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.

The term "partially or completely halogenated" will be taken to mean that 1 or more, e.g. 1, 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine. A partially or completely halogenated radical is termed below also "halo-radical". For example, partially or completely halogenated alkyl is also termed haloalkyl.

The term "alkyl" as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 12 carbon atoms (= Ci-Ci2-alkyl), frequently from 1 to 6 carbon atoms (= Ci-Ce-alkyl), in particular 1 to 4 carbon atoms (= Ci-C4-alkyl) and especially from 1 to 3 carbon atoms (= Ci-Cs-alkyl) or 1 or 2 carbon atoms (= Ci-C2-alkyl). Ci-C2-Alkyl is methyl or ethyl. Ci-Cs-Alkyl is methyl, ethyl, n-propyl or iso-propyl. Examples of Ci-C4-alkyl are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl (= secbutyl), isobutyl and tert-butyl. Examples for Ci-Ce-alkyl are, in addition to those mentioned for Ci-C4-alkyl, n-pentyl, 1- methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-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-methy I propyl. Examples for Ci-Cs-alkyl are, in addition to those mentioned for Ci-Ce-alkyl, n-heptyl, 1 -methylhexyl, 2-methylhexyl, 3-methylhexyl, 4- methylhexyl, 5-methylhexyl, 1 -ethylpentyl, 2-ethylpentyl, 3-ethy I pentyl, n-octyl, 1 -methylheptyl, 2-methylheptyl, 1- ethylhexyl, 2-ethylhexyl, 1 ,2-dimethylhexyl, 1 -propyl pentyl and 2-propyl pentyl. Examples for Ci-Ci2-alkyl are, apart those mentioned for Ci-Cs-alkyl, nonyl, decyl, 2-propylheptyl, 3-propylheptyl, undecyl, dodecyl and positional isomers thereof.

The term "haloalkyl" as used herein (and in the haloalkyl moieties of other groups comprising a haloalkyl group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl), which is also expressed as "alkyl which is partially or fully halogenated", denotes in each case a straight-chain or branched alkyl group having usually from 1 to 6 carbon atoms (= Ci-Ce-haloalkyl), more frequently 1 to 3 carbon atoms (= Ci-Cs-haloalkyl), as defined above, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moieties are selected from Ci-Cs-haloalkyl, specifically from Ci-C2-haloalkyl, in particular from fluorinated Ci-C2-alkyl. Examples for Ci-C2-haloalkyl are fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, 1- fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 1 -chloroethyl, 2-chloroethyl, 2,2,- dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1- bromoethyl, and the like. Examples for Ci-Cs-haloalkyl are, in addition to those mentioned for Ci-C2-haloalkyl, 1- fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1, 1 ,1- trifluoroprop-2-yl, 3-chloropropyl, and the like.

The term "hydroxyalkyl" denotes in each case a straight-chain or branched alkyl group having usually from 1 to 6 carbon atoms (= Ci-Ce-hydroxy alky I), more frequently 1 to 3 carbon atoms (= Ci-Ca-hydroxy alky I), as defined above, wherein one hydrogen atom of this group is replaced with a hydroxyl group. Examples are hydroxymethyl, 1- hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1 -hydroxy-2-propyl and the like. The term "alkenyl" as used herein denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 12 (= C2-Ci2-alkenyl), preferably 2 to 6 carbon atoms (= C2-C6-alkenyl), e.g. 3 to 6 carbon atoms (= Ca-Ce-alkenyl), in particular 2 to 4 carbon atoms (= C2-C4-alkenyl) or 2 or 3 carbon atoms (= C2-C3-alkenyl), and a double bond in any position, for example C2-C3-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl or 1- methylethenyl; C2-C4-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 or 2-methyl-2-propenyl; 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, 1 -ethyl-2-methyl-2-propenyl and the like, or C2-Ci2-alkenyl, such as the radicals mentioned for C2-Ce-alkenyl and additionally 1 -heptenyl, 2-heptenyl, 3- heptenyl, 1 -octenyl, 2-octenyl, 3-octenyl, 4-octenyl, the nonenyls, decenyls, undecenyls, dodecenyls and the positional isomers thereof.

Examples for Cs-Ce-alkenyl are those mentioned above for C2-Ce-alkenyl , except for ethenyl.

The term "haloalkenyl" as used herein, which may also be expressed as "alkenyl which is substituted by halogen", and the haloalkenyl moieties in haloalkenyloxy and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 6 (= C2-Ce-haloalkenyl) or 2 to 4 (= C2-C4-haloalkenyl) or 2 to 3 (= C2-C3- haloal keny I) carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.

The term "alkynyl" as used herein denotes unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 12 (= C2-Ci2-alkynyl), frequently 2 to 6 (= C2-C6-alkynyl), preferably 2 to 4 carbon atoms (= C2-C4-alkynyl) or 2 to 3 carbon atoms (= C2-C3-alkynyl) and a triple bond in any position, for example C2-C3-alkynyl, such as ethynyl, 1-propynyl or 2-propynyl; C2-C4-alkynyl, such as ethynyl, 1-propynyl or 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl and the like; C2-Ce-alkynyl_J such as 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, 1 -ethyl-1 -methyl-2-propynyl and the like.

The term "haloalkynyl" as used herein, which is also expressed as "alkynyl which is substituted by halogen", refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 6 carbon atoms (= C2-C6- haloal kyny I), preferabyl 2 to 4 carbon atoms (= C2-C4-haloalky nyl) or 2 or 3 carbon atoms (= C2-C3-haloalky ny I), and a triple bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.

The term "cycloalkyl" as used herein (and in the cycloalkyl moieties of other groups comprising a cycloalkyl group, e.g. cycloalkoxy and cycloalkylalkyl) denotes in each case a mono- or bicyclic, saturated cycloaliphatic radical having usually from 3 to 8 carbon atoms (= Ca-Cs-cycloalkyl), preferably 3 to 6 carbon atoms (= Ca-Ce-cycloalkyl), 3 to 5 carbon atoms (= Ca-Cs-cycloalkyl) or 3 to 4 carbon atoms (= C3-C4-cycloalkyl) as (only) ring members. Examples of monocyclic saturated cycloaliphatic radicals having 3 or 4 carbon atoms comprise cyclopropyl and cyclobutyl. Examples of monocyclic saturated cycloaliphatic radicals having 3 to 5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl. Examples of monocyclic saturated cycloaliphatic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic saturated cycloaliphatic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Cs-Ce-Cycloalkyl is cyclopentyl or cyclohexyl. Examples of bicyclic radicals having 6 to 8 carbon atoms comprise bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.

The term " halocycloal ky I" as used herein (and in the halocycloalky I moieties of other groups comprising an halocycloalkyl group) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 8 carbon atoms ("Cs-Cs-halocycloalkyl”), preferably 3 to 5 carbon atoms (“Cs-Cs-halocycloalkyl”), wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine. Examples are

1- and 2- fluorocyclopropyl, 1 ,2-, 2,2- and 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl, 2, 2,3,3- tetrafluorocyclpropyl, 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1 ,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1-,2- and 3-fluorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1-,2- and 3-chlorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlorocyclopentyl and the like.

The term "hydroxycycloalkyl" denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 6 carbon atoms (“hydroxy-(C3-C6)-cycloalkyl”), preferably 3 to 5 carbon atoms ("hydroxy-(C3-C5)-cycloalkyl”), wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms are replaced by a hydroxyl group. Examples are 1- hydroxycyclopropyl, 2-hydroxycyclopropyl, 1,2-dihydroxycyclopropyl, 2,3-dihydroxycyclopropyl, 1 -hydroxycyclobutyl,

2-hydroxycyclobutyl, 3-hydroxycyclobutyl, 1 ,2-dihydroxycyclobutyl, 1 ,3-dihydroxycyclobutyl, 2,3-dihydroxycyclobutyl, 1 -hydroxycyclopentyl, 2-hydroxycyclopentyl, 3-hydroxycyclopentyl, 1 ,2-dihydroxycyclopentyl, 1 ,3- dihydroxycyclopentyl, 2,3-dihydroxycyclopentyl and the like.

The term "alkoxy" as used herein denotes in each case a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms (= Ci-Ce-alkoxy), preferably 1 to 3 carbon atoms (= Ci-Ca-alkoxy), in particular 1 or 2 carbon atoms (= Ci-C2-alkoxy), which is bound to the remainder of the molecule via an oxygen atom. Ci-C2-Alkoxy is methoxy or ethoxy. Ci-Ca-Alkoxy is additionally, for example, n-propoxy or 1 -methylethoxy (isopropoxy). Ci-Ce- Alkoxy is additionally, for example, butoxy, 1 -methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1- di methylethoxy (tert-butoxy), pentoxy, 1 -methyl butoxy, 2-methylbutoxy, 3-methylbutoxy, 1 , 1 -dimethylpropoxy, 1,2- dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethyl propoxy, 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-ethy I butoxy, 1 ,1,2-trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1- ethyl-1 -methylpropoxy or 1 -ethyl-2-methylpropoxy.

The term "haloalkoxy" as used herein denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 6 carbon atoms (= Ci-Ce-haloalkoxy), preferably 1 to 3 carbon atoms (= Ci-Ca-haloalkoxy), in particular 1 or 2 carbon atoms (= Ci -C2-haloalkoxy), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms (in this case, the radical is also termed fluorinated alkoxy). Ci-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, 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 or OC2F5 Ci-Cs-Haloalkoxy is additionally, for example, 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, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1- (CH2CI)-2-chloroethoxy or 1-(CH2Br)-2-bromoethoxy. Ci-Ce-Haloalkoxy is additionally, for example, 4-fluorobutoxy, 4- chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy , 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

The term "alkenyloxy" denotes an alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Alkenyloxy is a C2-Ce-alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. Cs-Ce-Alkenyloxy is a Cs-Ce-alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.

The term "haloalkenyloxy" denotes a haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Haloalkenyloxy is a C2-Ce-haloal keny I group, as defined above, attached via an oxygen atom to the remainder of the molecule. Cs-Ce-Haloalkenyloxy is a Cs-Ce-haloalkeny I group, as defined above, attached via an oxygen atom to the remainder of the molecule.

The term "alkynyloxy" denotes an alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Alkynyloxy is a C2-Ce-alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. Cs-Ce-Alkynyloxy is a Cs-Ce-alky ny I group, as defined above, attached via an oxygen atom to the remainder of the molecule. The term "haloalkynyloxy" denotes a haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Haloalkynyloxy is a C2-C6-haloal ky ny I group, as defined above, attached via an oxygen atom to the remainder of the molecule. Ca-Ce-Haloalkynyloxy is a Ca-Ce-haloalky nyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.

The term "cycloalkoxy" denotes a cycloalkyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. Ca-Ce-Cycloalkoxy is a Ca-Ce-cycloal ky I group, as defined above, attached via an oxygen atom to the remainder of the molecule. Examples of Cs-Ce-cycloalkoxy comprise cyclopropoxy, cyclobutoxy, cyclopentoxy and cyclohexoxy.

The term "alkoxy-alkoxy" as used herein, refers to an alkoxy group, as defined above, where one hydrogen atom is replaced by another alkoxy group, as defined above. The term "Ci-Ca-alkoxy-Ci-Ca-alkoxy" as used herein, refers to an alkoxy group having 1 to 3 carbon atoms, as defined above, where one hydrogen atom is replaced by a C1-C3- alkoxy group, as defined above. Examples are methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, 1 -methoxyethoxy, 1 -ethoxyethoxy, 1 -propoxyethoxy, 1 -isopropoxyethoxy, 2-methoxyethoxy, 2- ethoxyethoxy, 2-propoxyethoxy, 2-isopropoxyethoxy, 1-methoxypropoxy, 1-ethoxypropoxy, 1-propoxypropoxy, 1- isopropoxypropoxy, 2-methoxypropoxy, 2-ethoxypropoxy, 2-propoxypropoxy, 2-isopropoxypropoxy, 3- methoxypropoxy, 3-ethoxypropoxy, 3-propoxypropoxy, 3-isopropoxypropoxy, and the like.

The term "alkylthio" (also alkylsulfanyl, "alkyl-S" or "alkyl-S(O)_k" (wherein k is 0) as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 6 carbon atoms (= C1- Ce-alkylthio), preferably 1 to 3 carbon atoms (= Ci-Cs-alkylthio), which is attached via a sulfur atom at any position in the alkyl group. Ci-C2-Alkylthio is methylthio or ethylthio. Ci-Cs-Alkylthio is additionally, for example, n-propylthio or

1 -methylethylthio (isopropylthio). Ci-Ce-Alkylthio is additionally, for example, butylthio, 1-methylpropylthio (secbutylthio), 2-methylpropylthio (isobutylthio), 1 , 1-dimethylethylthio (tert-butylthio), pentylthio, 1 -methylbutylthio,

2-methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1- ethylpropylthio, hexylthio, 1 -methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 , 1- dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethylbutylthio, 2-ethylbutylthio, 1 ,1 ,2-trimethylpropylthio, 1 ,2,2-trimethylpropylthio, 1-ethyl-1- methylpropylthio or 1 -ethyl-2-methylpropylthio.

The term "haloalkylthio" as used herein refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or completely substituted by fluorine, chlorine, bromine and/or iodine. Ci-C2-Haloalkylthio is, for example, SCH2F, SCHF2, SCF3, SCH2CI, SCHCI2, SCCI3, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio,

2.2.2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,

2.2.2-trichloroethylthio or SC2F5. Ci-C4-Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3- fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3- dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH2- C2F5, SCF2-C2F5, 1-(CH2F)-2-fluoroethylthio, 1-(CH2CI)-2-chloroethylthio, 1-(CH2Br)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. Ci-Ce-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6- fluorohexy Ithio, 6-chlorohexy Ithio, 6-bromohexylthio, 6-iodohexy Ithio or dodecafluorohexylthio.

The term "alkylsulfinyl" denotes an alkyl group, as defined above, attached via a sulfinyl [S(O)] group. For example, the term "Ci-C2-alkylsulfinyl" refers to a Ci-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-Ca-alkylsulfinyl" refers to a Ci-Cs-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-Ce-alkylsulfinyl" refers to a Ci-Ce-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. C1-C2- alkylsulfinyl is methylsulfinyl or ethylsulfinyl. Ci-Cs-alkylsulfinyl is additionally, for example, n-propylsulfinyl or 1-methylethylsulfinyl (isopropylsulfinyl). Ci-Ce-alkylsulfinyl is additionally, for example, butylsulfinyl, 1-methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl), 1 , 1-dimethylethylsulfinyl (tertbutylsulfinyl), pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl,

1.1-dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1 -ethylpropylsulfinyl, hexylsulfinyl, 1- methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1 ,1 -dimethylbutylsulfinyl,

1.2-dimethylbutylsulfinyl, 1 ,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3- dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1 ,1 ,2-trimethylpropylsulfinyl, 1 ,2,2- trimethylpropylsulfinyl, 1-ethyl-1 -methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.

The term "haloalkylsulfinyl" denotes a haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group to the remainder of the molecule. Ci-C2-Haloalkylsulfinyl is, for example, S(O)CH2F, S(O)CHF2, S(O)CF3, S(0)CH2CI, S(0)CHCl2, S(0)CCl3, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2- fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2- trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl,

2.2.2-trichloroethylsulfinyl or S(O)C2F5. Ci-Cs-Haloalkylsulfinyl is additionally, for example, 2-fluoropropylsulfinyl, 3- fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3- trichloropropylsulfinyl, S(O)CH2-C2F5, S(O)CF2-C2F5, 1-(CH2F)-2-fluoroethylsulfinyl, 1-(CH2CI)-2-chloroethylsulfinylor 1-(CH2Br)-2-bromoethylsulfinyl. Ci-C4-Haloalkylsulfinyl is additionally, for example, 4-fluorobutylsulfinyl, 4- chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl. Ci-Ce-Haloalkylsulfinyl is additionally, for example, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6- fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.

The term "alkylsulfonyl" denotes an alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term "Ci-C2-alkylsulfonyl" refers to a Ci-C2-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term

"Ci-Cs-alkylsulfonyl" refers to a Ci-Cs-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term

"Ci-Ce-alkylsulfonyl" refers to a Ci-Ce-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. C1-C2- alkylsulfonyl is methylsulfonyl or ethylsulfonyl. Ci-Cs-alkylsulfonyl is additionally, for example, n-propylsulfonyl or

1 -methylethylsulfonyl (isopropylsulfonyl). Ci-Ce-alkylsulfonyl is additionally, for example, butylsulfonyl, 1 -methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl), 1, 1 -dimethylethylsulfonyl (tertbutylsulfonyl), pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1 -dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1 -ethylpropylsulfonyl, hexylsulfonyl, 1 -methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1, 1 -dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1 ,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1 -ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1 , 1,2- trimethylpropylsulfonyl, 1 ,2,2-trimethylpropylsulfonyl, 1-ethyl-1 -methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl. The term "haloalkylsulfonyl" denotes a haloalkyl group, as defined above, attached via a sulfonyl [S(O)2] group to the remainder of the molecule. Ci-C2-Haloalkylsulfonyl is, for example, S(O)2CH2F, S(O)2CHF2, S(O)2CF3, S(O)2CH2CI, S(O)2CHCl2, S(O)₂CCl3, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2- fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2- trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2- fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl or S(O)2C2F5. Ci-Cs-Haloalkylsulfonyl is additionally, for example, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,

2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl,

3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, S(O)2CH2-C2F5, S(O)2CF2-C2F5, 1- (CH2F)-2-fluoroethylsulfonyl, 1-(CH2CI)-2-chloroethylsulfonylor 1-(CH2Br)-2-bromoethylsulfonyl. C1-C4- Haloalkylsulfonyl is additionally, for example, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl. Ci-Ce-Haloalkylsulfonyl is additionally, for example, 5-fluoropentylsulfonyl, 5- chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl, undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl, 6- chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl.

The substituent "oxo" replaces a CH2 group by a C(=O) group.

The suffix "-carbonyl" in a group denotes in each case that the group is bound to the remainder of the molecule via a carbonyl C=O group. This is the case e.g. in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, arylcarbonyl.

The term "alkoxycarbonyl" denotes an alkoxy group, as defined above, attached via a carbonyl [C(=O)] group to the remainder of the molecule. Ci-Cs-Alkoxycarbonyl is a Ci-Cs-alkoxy group, as defined above, attached via a carbonyl [C(=O)] group to the remainder of the molecule. Examples for Ci-Cs-alkoxycarbonyl are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl and isopropoxycarbonyl. Ci-Ce-Alkoxycarbonyl is a Ci-Ce-alkoxy group, as defined above, attached via a carbonyl [C(=O)] group to the remainder of the molecule. Examples for Ci-Ce-alkoxycarbonyl are, in addition to those listed for Ci-Cs-alkoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, isobutoxycarbonyl, tert-butoxycarbonyl, pentoxycarbonyl and hexoxycarbonyl.

The term "haloalkoxycarbonyl" denotes a haloalkoxy group, as defined above, attached via a carbonyl [C(=O)] group to the remainder of the molecule. Ci-Cs-Halolkoxycarbonyl is a Ci-Cs-haloalkoxy group, as defined above, attached via a carbonyl [C(=O)] group to the remainder of the molecule. Examples for Ci-Cs-haloalkoxycarbonyl are - C(O)OCH₂F, -C(O)OCHF₂, -C(O)OCF₃, -C(0)0CH₂CI, -C(0)0CHCI₂, -C(0)0CCI₃, chlorofluoromethoxycarbonyl, dichlorofluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-chloro-2- fluoroethoxycarbonyl, 2-chloro-2,2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, -C(O)OC2F5, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2,2- difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2,3- dichloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 3,3,3- trichloropropoxycarbonyl, -C(O)OCH2-C2F5, -C(O)OCF2-C2F5, 1-(CH2F)-2-fluoroethoxycarbonyl, 1-(CH2CI)-2- chloroethoxycarbonyl or 1-(CH2Br)-2-bromoethoxycarbonyl.

The term "alkoxycarbonyl-alkyl" denotes an alkyl group, as defined above, in which one hydrogen atom is replaced by an alkoxycarbonyl group, as defined above. Ci-Ce-Alkoxycarbonyl-Ci-Ce-alkyl is a Ci-Ce-alkyl group, as defined above, in which one hydrogen atom is replaced by a Ci-Ce-alkoxycarbonyl group, as defined above. Phenyl-(Ci-C2)-alkyl is a Ci-C2-alkyl group, as defined above, in which one hydrogen atom is replaced by a phenyl ring (i.e. the attachment to the remainder of the molecule is via the alkyl group). Examples are benzyl, 1 -phenylethyl and 2-phenylethyl. Phenyl-(Ci-C3)-alkyl is a Ci-Cs-alkyl group, as defined above, in which one hydrogen atom is replaced by a phenyl ring (i.e. the attachment to the remainder of the molecule is via the alkyl group). Examples are benzyl, 1 -phenylethyl, 2-phenylethyl, 1 -phenylpropyl, 2-phenylpropyl, 3-phenylpropyl or 2-phenyl-2-propyl. Furanyl-(Ci-C3)-alkyl is a Ci-Cs-alkyl group, as defined above, in which one hydrogen atom is replaced by a 2-or 3- furanyl ring (i.e. the attachment to the remainder of the molecule is via the alkyl group). Examples are furan-2-y I- methyl, furan-3-yl-methyl, 1-(furan-2-yl)-ethyl, 1-(furan-3-yl)-ethyl, 2-(furan-2-yl)-ethyl, 2-(furan-3-yl)-ethyl and the like. Phenylthio is a phenyl ring attached via an S atom to the remainder of the molecule.

Phenylsulfinyl is a phenyl ring attached via a S(O) group to the remainder of the molecule. Phenylsulfonyl is a phenyl ring attached via a S(O)2 group to the remainder of the molecule.

The term "aryl" as used herein refers to a polyunsaturated, aromatic hydrocarbyl group having a single ring (i.e. phenyl) or multiple aromatic rings fused together (e.g. naphthyl), typically containing 5 to 12 atoms; preferably 6 to 10, wherein at least one ring is aromatic. Examples of aryl groups include but are not limited to phenyl, naphthyl, anthracyl. Preferred aryl group according to the invention is phenyl.

The term "arylalkyl" as used herein refers to a group -alkyl-aryl, wherein alkyl and aryl are as herein defined. Examples of arylalkyl groups include but are not limited to benzyl.

The term "aryloxycarbonyl" as used herein refers to a group -C(O)-O-aryl, wherein aryl is as herein defined. Nonlimiting examples of aryloxycarbonyl include phenyloxycarbonyl.

An unsaturated carbocycle contains at least one C-C double bond(s).

An unsaturated heterocycle contains at least one C-C and/or C-N and/or N-N double bond(s).

Partially unsaturated carbocycles contain less than the maximum number of C-C double bond(s) allowed by the ring size.

Partially unsaturated heterocycles contain less than the maximum number of C-C and/or C-N and/or N-N double bond(s) allowed by the ring size.

Examples for three-, four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic carbocycles are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloprop-1 -enyl, cycloprop-2-enyl, cyclobut-1 -enyl, cyclobut-2-enyl, cyclobutadienyl, cyclopent- 1 -enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclopenta-1, 3-dienyl, cyclopenta-1, 4-dienyl, cyclopenta-2, 4-dienyl, cyclohex-1 -enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohexa-1, 3- dienyl, cyclohexa-1, 4-dienyl, cyclohexa-1, 5-dienyl, cyclohexa-2, 4-dienyl, cyclohexa-2, 5-dienyl, phenol and the like. Examples for three-, four-, five- six or or seven-membered saturated, partly unsaturated, fully unsaturated or aromatic heterocycles are: 3-, 4-, 5- or 6-membered monocyclic saturated heterocycle: e.g. oxiran-2-yl, thiiran-2-yl, aziridin-1-yl, aziridin-2-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, 1-oxothietan-2-yl, 1-oxothietan-3-yl, 1 ,1-dioxothietan-2-yl, 1,1- dioxothietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien- 2-yl, tetrahydrothien-3-yl, 1-oxotetrahydrothien-2-yl, 1 ,1-dioxotetrahydrothien-2-yl, 1-oxotetrahydrothien-3-yl, 1,1- dioxotetrahydrothien-3-yl, 1,3-dioxolan-2-yl, 1 ,3-dioxolan-4-yl, 1,3-ditholan-2-yl, 1 ,3-ditholan-4-yl, 1 ,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1 ,3-oxathiolan-5-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl, thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl, isothiazolidin- 5-yl, 1,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl, 1,3,4- oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 1 ,3-dioxan- 2-yl, 1,3-dioxan-4-yl, 1 ,3-dioxan-5-yl, 1 ,4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-1-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, morpholin- 2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-2- yl, 1 oxothiomorpholin-3-yl, 1-oxothiomorpholin-4-yl, 1,1 dioxothiomorpholin-2-yl, 1,1 dioxothiomorpholin-3-yl, 1,1- dioxothiomorpholin-4-yl, and the like;

5- or 6-membered monocyclic partially unsaturated heterocycles: e.g. 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl,

2.5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5- dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl,

4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4- isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4- isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol- 2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4- dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl,

4.5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4- yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-

5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,6-dihydro-2H-pyran-2-, -3-, -4-, -5- or 6- yl, 3,4-dihydro-2H-pyran-2-, -3-, -4-, -5- or 6-yl, 3,6-dihydro-2H-thiopyran-2-, -3-, -4-, -5- or 6-yl, 3,4-dihydro-2H- thiopyran-2-, -3-, -4-, -5- or 6-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl;

If two radicals bound on the same nitrogen atom (for example R^b and R^h, R^b2 and R^b3), together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered, saturated N-bound heterocyclic ring which may contain as a ring member a further heteroatom or heteroatom group selected from the group consisting of N, 0, S, S(0) and S(0)2, this is for example aziridn-1-yl, azetidin-1-yl, pyrrolidin-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, thiazolidin-3-yl, isoxazolidin-2-yl, isothiazolin-2-yl, piperidin-1-yl, piperazin-1 -yl, morpholin-1-yl, thiomorpholin-1-yl, 1-oxothiomorpholin-1-yl, 1 ,1-dioxothiomorpholin-1-yl, azepan-1-yl or 1 ,4-diazepan-1-yl. The remarks made below as to preferred embodiments of the variables (substituents) of the compounds of formula I are valid on their own as well as preferably in combination with each other, as well as in combination with the stereoisomers, tautomers or salts thereof.

The remarks made below concerning preferred embodiments of the variables further are valid on their own as well as preferably in combination with each other concerning the compounds of formula I, where applicable, as well as concerning the uses and methods according to the invention and the composition according to the invention.

Compounds of formula (I), wherein R⁷ is methyl or ethyl, and the other variables are as defined herein, have a stereocenter (#) at the carbon with the R⁷/R⁹ substitution, which can be in S- or R-configuration. In the context of the present invention, compounds of formula (I), wherein R⁷ is methyl or ethyl, and the other variables are as defined herein, which are in the R-configuration at the stereocenter, i.e. compounds of formula (I.R), are preferred.

Preferably, R¹ is hydrogen or (Ci-C3)-alkyl, and is more preferably hydrogen.

Preferably, R⁸ is hydrogen or (Ci-C3)-alkyl, and is more preferably hydrogen.

Preferably, R¹ and R⁸ are both hydrogen.

Preferably, R² is hydrogen, halogen or (Ci-C3)-alkyl. More preferably, R² is hydrogen or halogen, e.g. H, F or Cl. In particular, R² is hydrogen.

Preferably, R⁶ is hydrogen, halogen or (Ci-C3)-alkyl. More preferably, R⁶ is hydrogen.

Preferably, R² and R⁶, independently of each other, are hydrogen, halogen or (Ci-C3)-alkyl. More preferably, R² is hydrogen or halogen, e.g. H, F or Cl, and R⁶ is hydrogen. In particular, R² is hydrogen and R⁶ is hydrogen.

Preferably, R³ is hydrogen, halogen, (Ci-C3)-alkyl, (Ci-CsJ-haloalkyl, (Ci-C3)-alkoxy or (Ci-C3)-haloalkoxy. More preferably, R³ is hydrogen, halogen, (Ci-C2)-alkyl, (Ci-C2)-haloalkyl, (Ci-C2)-alkoxy or (Ci-C2)-haloalkoxy. Most preferably, R³ is hydrogen or halogen, in particular H, F, Cl or Br.

Preferably, R⁵ is hydrogen, halogen, (Ci-C3)-alkyl, (Ci-CsJ-haloalkyl, (Ci-C3)-alkoxy or (Ci-C3)-haloalkoxy. More preferably, R⁵ is hydrogen, halogen or (Ci-C2)-alkoxy. Most preferably, R⁵ is hydrogen or halogen, in particular H, F, Cl or Br. Preferably R³ and R⁵, independently of each other, are hydrogen, halogen, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (C1-C3)- alkoxy or (Ci-C3)-haloalkoxy. More preferably, R³ is hydrogen, halogen, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (C1-C3)- alkoxy or (Ci-C3)-haloalkoxy and R⁵ is hydrogen, halogen or (Ci-C2)-alkoxy. In particular, R³ and R⁵, independently of each other, are hydrogen or halogen. More particularly, R³ is halogen and R⁵ is hydrogen or halogen.

In another preferred embodiment, R³ is hydrogen, halogen, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (Ci-C3)-alkoxy or (C1-C3)- haloalkoxy and R⁵ is hydrogen or halogen. More preferably, R³ is hydrogen, halogen, (Ci-C2)-alkyl, (Ci-C2)-haloalkyl, (Ci-C2)-alkoxy or (Ci-C2)-haloalkoxy and R⁵ is hydrogen or halogen.

Preferably, R⁴ is hydrogen or halogen. In particular, R⁴ is hydrogen.

R⁷ is methyl or ethyl, preferably methyl.

Preferably, X is oxygen.

Preferably, R¹⁰ is methyl or ethyl. In particular, R¹⁰ is methyl.

Embodiment Q.1 : Preferably, Q represents the radical of formula (Z-Y),

(Z-Y)

R¹⁰ is methyl;

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

R¹⁰ and R¹⁴ form, together with the carbon atoms to which they are bound, a four- to six-membered saturated or partially unsaturated carbocycle or a five-membered saturated or partially unsaturated heterocycle containing 1 oxygen, nitrogen or sulfur atom as ring members;

R^b is hydrogen or (Ci-Cej-alkyl, (C2-C4)-alkenyl, (C3-C4)-alkynyl, (Cs-Cej-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C3)- alkyl, phenyl-(Ci-C3)-alkyl or furanyl-(Ci-C3)-alkyl, where each of the seven last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkoxy, (Ci-Csj-alkylthio, (Ci-Csj-alkylsulfinyl, (Ci-Csj-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R^b1 and R^b2 independently of each other are hydrogen or have one of the meanings given for R^a;

R^b3 is hydrogen or (Ci-C6)-alkyl, (C2-C4)-alkenyl, (C3-C4)-alkynyl, (Cs-CeJ-cycloalkyl, (C3-C6)-cycloalkyl-(Ci-C3)- alkyl, phenyl-(Ci-C3)-alkyl or furanyl-(Ci-C3)-alkyl, where each of the seven last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkoxy, (Ci-C3)-alkylthio, (Ci-C3)-alkylsulfinyl, (Ci-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; or

R^b2 and R^b3 form, together with the nitrogen atom to which they are bound, a saturated 3-, 4-, 5-, 6- or 7-membered N-bound heterocycle which may contain one further heteroatom or heteroatom group selected from the group consisting of N, 0, S, S(0) and S(0)2 as ring member; each R^e is independently hydrogen or (Ci-C6)-alkyl, (C2-C4)-alkenyl, (C3-C4)-alkynyl, (Cs-CeJ-cycloalkyl, (Cs-Ce)- cycloalkyl-(Ci-C3)-alkyl, phenyl-(Ci-C3)-alkyl or furanyl-(Ci-C3)-alkyl, where each of the seven last- mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkoxy, (Ci-C2)-haloalkoxy, (Ci-C3)-alkylthio, (Ci-C3)-haloalkylthio, (C1-C3)- alkylsulfinyl, (Ci-C3)-haloalkylsulfinyl, (Ci-C3)-alkylsulfonyl, (Ci-C3)-haloalkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

R^h is hydrogen or (Ci-CeJ-alkyl, (Ci-C2)-alkoxy, (Cs-CeJ-cycloalkyl, (C2-C4)-alkenyl, (Ci-C6)-alkoxycarbonyl-(Ci- Ce)-alkyl, or (C3-C4)-alkynyl, where each of the six last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkyl, (Ci-C2)-alkoxy and (Ci-C2)-alkoxy-(Ci-C2)-alkoxy; or

R^b and R^h form, together with the nitrogen atom to which they are bound, a saturated 5-, 6- or 7-membered N-bound heterocycle which may contain one further heteroatom or heteroatom group selected from the group consisting of N, 0, S, S(0) and S(0)2 as ring member; m is independently of each occurrence 0, 1, 2 or 3; n is 1.

In another embodiment the present invention relates to compounds, wherein Q is defined as in embodiment Q.1 , wherein

R¹⁰ is methyl;

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

R¹⁰ and R¹⁴ form, together with the carbon atoms to which they are bound, a four- to six-membered saturated or partially unsaturated carbocycle or a five-membered partially unsaturated heterocycle containing 1 oxygen, nitrogen or sulfur atom as ring members;

Embodiment Q.2: More preferably, Q represents the radical of formula (Z-Y),

(Z-Y)

wherein the arrow represents the bond to the adjacent nitrogen atom, and wherein the substituents have the following meanings R¹⁰ is methyl;

R¹¹, R¹², R¹³, R¹⁴are hydrogen; or

R¹⁰ and R¹⁴ form, together with the carbon atoms to which they are bound, a four- to six-membered saturated or partially unsaturated carbocycle or a five-membered saturated or partially unsaturated heterocycle containing 1 oxygen atom as ring member;

Y is CO₂R^e, CONR^bR^h, or CONR^eSO₂R^a; each R^a is independently (Ci-Ce)-alkyl, (Ci-Cej-haloalkyl, (C3-C4)-alkynyl or (Cs-Cej-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (Ci-Caj-alkoxy;

R^b is hydrogen; each R^e is independently hydrogen or (Ci-Ce)-alkyl, or (Cs-Cej-cycloalkyl, where each of the two last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO₂R^a, (Ci-C₂)-alkoxy, (Ci-C₂)-haloalkoxy, (Ci-Csj-alkylthio, (Ci-Csj-haloalkylthio, (C1-C3)- alkylsulfinyl, (Ci-Csj-haloalkylsulfinyl, (Ci-Csj-alkylsulfonyl, (Ci-Csj-haloalkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

R^h is hydrogen or (Ci-Cej-alkyl, (Ci-C₂)-alkoxy, (Cs-Cej-cycloalkyl, (C₂-C4)-alkenyl, (Ci-Cej-alkoxycarbonyl- (Ci-Cej-alkyl, or (C3-C4)-alkynyl, where each of the six last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO₂R^a, (Ci-C₂)-alkyl, (Ci-C₂)-alkoxy and (Ci-C₂)-alkoxy-(Ci-C₂)-alkoxy; or

R^b and R^h form, together with the nitrogen atom to which they are bound, a saturated 6-membered N-bound heterocycle which may contain 1 oxygen atom as ring member; m is independently of each occurrence 0, 1 , or 2; n is 1.

In another embodiment the present invention relates to compounds, wherein Q is defined as in embodiment Q.2, wherein

R¹⁰ is methyl;

R¹¹, R¹², R¹³, R¹⁴are hydrogen; or

R¹⁰ and R¹⁴ form, together with the carbon atoms to which they are bound, a four- to six-membered saturated or partially unsaturated carbocycle or a five-membered partially unsaturated heterocycle containing 1 oxygen atom as ring member;

Embodiment Q.3: Most preferably, Q represents the radical of formula Z-Y, (Z-Y)

R¹¹, R¹², R¹³, R¹⁴are hydrogen; or

Y is CO₂R^e, CONR^bR^h, or CONR^eSO₂R^a;

R^a is (Ci-Cej-alkyl or (Ci-Cej-haloalkyl;

R^b is hydrogen; each R^e is independently hydrogen or (Ci-Cej-alkyl or (Ca-Cej-cycloalkyl, where each of the two last-mentioned radicals is substituted by m radicals selected from the group consisting of (Ci-C₂)-alkoxy, (C1-C3)- alkylthio, (Ci-Csj-alkylsulfinyl, (Ci-Caj-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

R^h is hydrogen or (Ci-Cej-alkyl, (Ci-C₂)-alkoxy, (Cs-Cej-cycloalkyl, (C₂-C4)-alkenyl, (Ci-Cej-alkoxycarbonyl- (Ci-Cej-alkyl, or (C3-C4)-alkynyl, where each of the six last-mentioned radicals is substituted by m radicals selected from the group consisting of (Ci-C₂)-alkyl, (Ci-C₂)-alkoxy and (Ci-C₂)-alkoxy-(Ci-C₂)- alkoxy; or

In another embodiment the present invention relates to compounds, wherein Q is defined as in embodiment Q.3, wherein

R¹⁰ is methyl;

R¹¹, R¹², R¹³, R¹⁴are hydrogen; or

Representative examples for Q representing the radical of formula Z-Y,

(Z-Y)

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; n is 1 or 2, are the following radicals Z¹-Y and Z²-Y:

(Z¹-Y) (Z2-Y)

Preferred examples for Q are radicals Z¹-Y and Z²-Y, wherein

Y is C0₂R^e;

R^e is hydrogen, (Ci-C6)-alkyl, or (Cs-CeJ-cycloalkyl.

Further representative examples for Q representing the radical of formula Z-Y,

R¹¹, R¹², R¹³ are hydrogen;

R¹⁰ and R¹⁴ form, together with the carbon atoms to which they are bound, a four- to six-membered saturated or partially unsaturated carbocycle or a five-membered saturated heterocycle containing 1 oxygen atom as ring member; n is 1 , are the following radicals Z³-Y to Z⁸-Y:

Preferred examples for Q are radicals Z³-Y to Z⁸-Y, wherein

Y is CO₂R^e, CONR^bR^h, or CONR^eSO₂R^a;

R^a is (Ci-Cej-alkyl or (Ci-Ce)-haloalkyl;

R^b is hydrogen; each R^e is independently hydrogen or (Ci-Ce)-alkyl or (Cs-Cej-cycloalkyl, where each of the two last-mentioned radicals is substituted by m radicals selected from the group consisting of (Ci-C₂)-alkoxy, (Ci-Csj-alkylthio, (Ci-Csj-alkylsulfinyl, (Ci-Csj-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

R^h is hydrogen or (Ci-Cej-alkyl, (Ci-C₂)-alkoxy, (Cs-Cej-cycloalkyl, (C₂-C4)-alkenyl, (Ci-Cej-alkoxycarbony l-(Ci- Cej-alkyl, or (C3-C4)-alkynyl, where each of the six last-mentioned radicals is substituted by m radicals selected from the group consisting of (Ci-C₂)-alkyl, (Ci-C₂)-alkoxy and (Ci-C₂)-alkoxy-(Ci-C₂)-alkoxy; or

R^b and R^h form, together with the nitrogen atom to which they are bound, a saturated 6-membered N-bound heterocycle which may contain 1 oxygen atom as ring member; m Is O, 1 , or 2; n is 1.

Embodiment E.1 : In a particular embodiment, in the compounds of formula (I), the substituents have the following meanings:

R¹ is hydrogen or (Ci-C3)-alkyl;

R² is hydrogen, halogen, or (Ci-C3)-alkyl;

R³ is hydrogen, halogen, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (Ci-C3)-alkoxy or (Ci-C3)-haloalkoxy;

R⁴ is hydrogen or halogen;

R⁵ is hydrogen, halogen, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (Ci-C3)-alkoxy or (Ci-C3)-haloalkoxy;

R⁶ is hydrogen, halogen, or (Ci-C3)-alkyl;

R⁷ is methyl or ethyl;

R⁸ is hydrogen or (Ci-C3)-alkyl;

R⁹ is hydrogen;

X is oxygen;

Q represents the radical of formula (Z-Y),

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

Y is CO₂R^e, CONR^bR^h, or CONR^eSO₂R^a;

R^a is (Ci-Cej-alkyl or (Ci-Ce)-haloalkyl;

R^b is hydrogen; each R^e is independently hydrogen or (Ci-CeJ-alkyl, or (Cs-CeJ-cycloalkyl, where each of the two last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkoxy, (Ci-C2)-haloalkoxy, (Ci-C3)-alkylthio, (Ci-C3)-haloalkylthio, (Ci-C3)-alkylsulfinyl, (Ci- C3)-haloalkylsulfinyl, (Ci-C3)-alkylsulfonyl, (Ci-C3)-haloalkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

R^h is hydrogen or (Ci-CeJ-alkyl, (Ci-C2)-alkoxy, (Cs-CeJ-cycloalkyl, (C2-C4)-alkenyl, (Ci-C6)-alkoxycarbonyl-(Ci- Ce)-alkyl, or (Cs-C^-alkynyl, where each of the six last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkyl, (Ci-C2)-alkoxy and (Ci-C2)-alkoxy-(Ci-C2)-alkoxy; or

In another aspect the present invention relates to compounds as defined in embodiment E.1 , wherein

R¹⁰ is methyl;

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

Embodiment E.2: In another particular embodiment, in the compounds of formula (I), the substituents have the following meanings:

R¹ is hydrogen or (Ci-C3)-alkyl;

R² is hydrogen, halogen, or (Ci-C3)-alkyl;

R⁴ is hydrogen or halogen;

R⁶ is hydrogen, halogen, or (Ci-C3)-alkyl;

R⁷ is methyl or ethyl;

R⁸ is hydrogen or (Ci-C3)-alkyl;

R⁹ is hydrogen;

X is oxygen;

Q represents the radical of formula (Z-Y),

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

Y is C0₂R^e, CONR^bR^h, or CONR^eSO₂R^a;

R^a is (Ci-Cej-alkyl, (Ci-Cej-haloalkyl, (C3-C4)-alkynyl or (Cs-Cej-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C1-C3)- alkoxy;

In another aspect the present invention relates to compounds as defined in embodiment E.2, wherein

R¹⁰ is methyl;

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

Embodiment E.3: In a further particular embodiment, in the compounds of formula (I), the substituents have the following meanings:

R¹ is hydrogen;

R² is hydrogen or halogen;

R³ is halogen;

R⁴ is hydrogen or halogen;

R⁵ is hydrogen or halogen;

R⁶ is hydrogen; R⁷ is methyl or ethyl;

R⁸ is hydrogen;

R⁹ is hydrogen;

X is oxygen;

Q represents the radical of formula (Z-Y),

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

Y is CO₂R^e, CONR^bR^h, or CONR^eSO₂R^a;

R^a is (Ci-Cej-alkyl or (Ci-Cej-haloalkyl;

R^b is hydrogen; each R^e is independently hydrogen or (Ci-Cej-alkyl, or (Ca-Cej-cycloalkyl, where each of the two last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO₂R^a, (Ci-C₂)-alkoxy, (Ci-C₂)-haloalkoxy, (Ci-Csj-alkylthio, (Ci-Caj-haloalkylthio, (Ci-Csj-alkylsulfinyl, (Ci- Caj-haloalkylsulfinyl, (Ci-Csj-alkylsulfonyl, (Ci-Csj-haloalkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

R^h is hydrogen or (Ci-Cej-alkyl, (Ci-C₂)-alkoxy, (Cs-Cej-cycloalkyl, (C₂-C4)-alkenyl, (Ci-Cej-alkoxycarbony l-(Ci- Cej-alkyl, or (C3-C4)-alkynyl, where each of the six last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO₂R^a, (Ci-C₂)-alkyl, (Ci-C₂)-alkoxy and (Ci-C₂)-alkoxy-(Ci-C₂)-alkoxy; or

R^b and R^h form, together with the nitrogen atom to which they are bound, a saturated 6-membered N-bound heterocycle which may contain 1 oxygen atom as ring member; m is independently of each occurrence 0, 1 , or 2; n is 1;

In another aspect the present invention relates to compounds as defined in embodiment E.3, wherein

R¹⁰ is methyl;

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

R¹⁰ and R¹⁴ form, together with the carbon atoms to which they are bound, a four- to six-membered saturated or partially unsaturated carbocycle or a five-membered partially unsaturated heterocycle containing 1 oxygen atom as ring member; Embodiment E.4: In a further particular embodiment, in the compounds of formula (I), the substituents have the following meanings:

R¹ is hydrogen;

R² is hydrogen or halogen;

R³ is halogen;

R⁴ is hydrogen or halogen;

R⁵ is hydrogen or halogen;

R⁶ is hydrogen;

R⁷ is methyl or ethyl;

R⁸ is hydrogen;

R⁹ is hydrogen;

X is oxygen;

Q represents the radical of formula (Z-Y),

(Z-Y)

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

Y is CO₂R^e, CONR^bR^h, or CONR^eSO₂R^a;

R^b and R^h form, together with the nitrogen atom to which they are bound, a saturated 6-membered N-bound heterocycle which may contain 1 oxygen atom as ring member; m is independently of each occurrence 0, 1 , or 2; is 1;

In another aspect the present invention relates to compounds as defined in embodiment E.4, wherein

R¹⁰ is methyl;

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

Embodiment E.5: In a further particular embodiment, in the compounds of formula (I), the substituents have the following meanings:

R¹ is hydrogen;

R² is hydrogen or halogen;

R³ is halogen;

R⁴ is hydrogen or halogen;

R⁵ is hydrogen or halogen;

R⁶ is hydrogen;

R⁷ is methyl or ethyl;

R⁸ is hydrogen;

R⁹ is hydrogen;

X is oxygen;

Q represents the radical of formula (Z-Y),

(Z-Y)

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

Y is CO₂R^e;

R^e is hydrogen or (Ci-Ce)-alky I or (Cs-Cej-cycloalky I, where each of the two last-mentioned radicals is substituted by m radicals selected from the group consisting of (Ci-C2)-alkoxy, (Ci-Csj-alkylthio, (Ci-Csj-alkylsulfinyl, (Ci- Caj-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; m is independently of each occurrence 0, 1 , or 2; n is 1. In another aspect the present invention relates to compounds as defined in embodiment E.5, wherein

R¹⁰ is methyl;

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

Embodiment E.6: In a further particular embodiment, in the compounds of formula (I.R), the substituents have the following meanings:

R¹ is hydrogen;

R² is hydrogen or halogen;

R³ is halogen;

R⁴ is hydrogen or halogen;

R⁵ is hydrogen or halogen;

R⁶ is hydrogen;

R⁷ is methyl or ethyl;

R⁸ is hydrogen;

R⁹ is hydrogen;

X is oxygen;

Q represents the radical of formula (Z-Y),

(Z-Y)

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

Y is CO₂R^e;

R^e is hydrogen or (Ci-Ce)-alky I or (Cs-Cej-cycloalky I, where each of the two last-mentioned radicals is substituted by m radicals selected from the group consisting of (Ci-C2)-alkoxy, (Ci-Csj-alkylthio, (Ci-Csj-alkylsulfinyl, (Ci- Caj-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; m is O, 1, or 2; n is 1.

In another aspect the present invention relates to compounds as defined in embodiment E.6, wherein

R¹⁰ is methyl; R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

R¹⁰ and R¹⁴ form, together with the carbon atoms to which they are bound, a four- to six-membered saturated or partially unsaturated carbocycle or a five-membered partially unsaturated heterocycle containing 1 oxygen atom as ring member; In the context of the present invention, compounds of formula (I) are particularly preferred, wherein R¹, R², R⁶, R⁸ and

R⁹ are hydrogen, R⁷ is methyl, X is oxygen, Q is any of Z¹-Y to Z⁸-Y, and R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 below:

Table 1 :

Compounds of formula 1.1 , wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is COCH, i.e. individual compounds 1.1.1 - 1.1.1944, are particularly preferred.

Compounds of formula 1.2, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is COOCH3, i.e. individual compounds 1.2.1 - 1.2.1944, are particularly preferred.

Compounds of formula 1.3, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is COOCH2CH3, i.e. individual compounds

1.3.1 - 1.3.1944, are particularly preferred.

Compounds of formula 1.4, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is COOCH(CH3)2, i.e. individual compounds

1.4.1 - 1.4.1944, are particularly preferred.

Compounds of formula 1.5, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is COOCH2CH(CH3)2, i.e. individual compounds 1.5.1 - 1.5.1944, are particularly preferred.

Compounds of formula 1.6, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is COOR^e and R^e is cyclobutyl, i.e. individual compounds 1.6.1 - 1.6.1944, are particularly preferred.

Compounds of formula 1.7, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is COOCH2CH2OCH3, i.e. individual compounds 1.7.1 - 1.7.1944, are particularly preferred.

Compounds of formula 1.8, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is COOCH2CH2SCH3, i.e. individual compounds 1.8.1 - 1.8.1944, are particularly preferred.

Compounds of formula 1.9, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is COOCH2CH2SC6H5 (CeHs is phenyl), i.e. individual compounds 1.9.1 - 1.9.1944, are particularly preferred.

Compounds of formula 1.10, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is COOCH2CH2S(O)2C6H5 (CeHs is phenyl), i.e. individual compounds 1.10.1 - 1.10.1944, are particularly preferred.

Compounds of formula 1.11, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is CONHCH2CH2OCH3, i.e. individual compounds 1.11.1 - 1.11.1944, are particularly preferred.

Compounds of formula 1.12, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is CONHOCH3, i.e. individual compounds

1.12.1 - 1.12.1944, are particularly preferred.

Compounds of formula 1.13, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is CONR^bR^h, wherein R^b and R^h, together with the nitrogen atom to which they are bound, form a saturated 6-membered heterocycle, containing one oxygen atom adjacent to the nitrogen atom, i.e. individual compounds 1.13.1 - 1.13.1944, are particularly preferred.

Compounds of formula 1.14, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is CONHCH(CH3)C(O)OCH3, i.e. individual compounds 1.14.1 - 1.14.1944, are particularly preferred.

Compounds of formula 1.15, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is CONHCH2CH2OCH2CH2OCH3, i.e. individual compounds 1.15.1 - 1.15.1944, are particularly preferred.

Compounds of formula 1.16, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is CONHC(CH3)2CCH, i.e. individual compounds 1.16.1 - 1.16.1944, are particularly preferred.

Compounds of formula 1.17, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is CONHS(O)2CH3, i.e. individual compounds 1.17.1 - 1.17.1944, are particularly preferred.

Compounds of formula 1.18, wherein R¹, R², R⁶, R⁸ and R⁹ are hydrogen, R⁷ is methyl, X is oxygen, R³, R⁴, R⁵ and Q have the meanings as defined lines in 1 to 1944 of Table 1 above and Y is CONHS(O)2CF3, i.e. individual compounds 1.18.1 - 1.18.1944, are particularly preferred.

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

General Scheme 1 :

The compounds of formula (I) can be prepared according to methods or in analogy to methods that are described in the prior art and are very well known and apply common amid and peptide coupling technics. The synthesis takes advantage of starting materials that are commercially available or may be prepared according to conventional procedures starting from readily available compounds. Compounds of the formula (I) can for example be prepared according to Scheme 1 from the compounds of formula (V) (when X = 0, L = OH, Cl or F; when X = S, L = Cl or F) and commercially available amino acids and esters (IV) to form benzoylamino esters (III). Such coupling reactions using acid chlorides and a base are for example described in Nadia, Klai; Malika, Berredjem; Nawel, Khettache; MedYazid, Belghit; Zine, Regainia; Aouf, Nour-Eddine, J. Heterocyclic Chem., 41, 57 (2004) or in Chen, Francis M. F.; Benoiton, N. Leo, Can. J. Chem. 1987, 65, 1224-1227 with common coupling reagents such as EDC/HOBt in WO 2010/084979 or can be achieved by using other coupling reagents, for example HATU (O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium-hexafluorphosphate), and an organic base.

To obtain the compounds of formula (I) the intermediates (III) can for example be converted to benzoylamino acids (II), e.g. by applying common saponification techniques such as treatment with a base, followed by a second coupling step with amines (VI) with similar methods as described above and which are common to somebody skilled in the art.

General Scheme 2:

Compounds of formula (I) might also for example be prepared according to Scheme 2 from the compounds of formula (V) (when X = 0, L = OH, Cl or F; when X = S, L = Cl or F) and appropriate amino precursors VII using similar coupling reactions as described above, and as exemplified below in the experimental part.

General Scheme 3:

Alternatively, compounds of formula (I) might also be prepared by modification of compounds (I) by example using an additional saponification/coupling step (Y = CO2R^e), as exemplified below in the experimental part.

General Scheme 4:

A thioamide of formula (I with X = S) can be prepared from the corresponding amide of formula (I with X = 0), according to Scheme 4 by using thionation reagent.

Preferably elemental sulfur (CAS: 7704-34-9), phosphorus pentasulfide (CAS: 1314-80-3), ammonium phosphorodithioate or Lawesson's reagent (CAS: 19172-47-5) are employed. Most preferably, Lawesson's reagent (CAS: 19172-47-5) is employed.

The reaction is typically carried out in an organic solvent. Preferably an aprotic organic solvent is used. Most preferably tetrahydrofuran (THF), 1,4-dioxane and toluene are used. The reaction is carried out at temperatures between room temperature to refluxing temperatures. Preferably, the reaction is carried out at refluxing temperatures.

Moreover, it may be useful to apply the compounds of formula (I) in combination with safeners. Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the compounds of the formula (I) towards undesired vegetation. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or postemergence application of the useful plant. The safeners and the compounds of formula (I) and optionally the herbicides B can be applied simultaneously or in succession.

In another embodiment of the present invention the combinations according to the present invention comprise at least one compound of formula (I) and at least one safener C (component C).

Examples of safeners are e.g. (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4- (aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such amides, esters, and thioesters, provided they have an acid group.

Examples of safener compounds C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl- 3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4). The active compounds C are known herbicides and safeners, see, 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, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998.

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

A formulation comprises a pesticidal ly effective amount of a compound of formula (I). The term "effective amount" denotes an amount of the combination or of the compound of formula (I), which is sufficient for controlling undesired vegetation, especially for controlling undesired vegetation in crops (i.e. cultivated plants) and which does not result in a substantial damage to the treated crop plants. Such an amount can vary in a broad range and is dependent on various factors, such as the undesired vegetation to be controlled, the treated crop plants or material, the climatic conditions and the specific compound of formula (I) used.

The compounds of formula (I) and their salts can be converted into customary types of formulations, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for formulation types are suspensions (e.g. SC, CD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EC, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further formulation types are defined in the "Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6^th Ed. May 2008, CropLife International.

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

Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxy lates, 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 with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. 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 sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines. Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of formula (I) on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples for formulation types and their preparation are:

I) Water-soluble concentrates (SL, LS)

10-60 wt% of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C) according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.

II) Dispersible concentrates (DC)

5-25 wt% of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C) according to the invention and 1-10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion. iii) Emulsifiable concentrates (EC)

15-70 wt% of compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C) according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion. iv) Emulsions (EW, EO, ES)

5-40 wt% of compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C) according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion. v) Suspensions (SC, CD, FS)

In an agitated ball mill, 20-60 wt% of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C)according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type formulation up to 40 wt% binder (e.g. polyvinylalcohol) is added. vi) Water-dispersible granules and water-soluble granules (WG, SG)

50-80 wt% of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C)according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, 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)

50-80 wt% of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C) according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance. viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt% of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C) according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. iv) Microemulsion (ME)

5-20 wt% of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C) according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion. iv) Microcapsules (CS) An oil phase comprising 5-50 wt% of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C) according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound of formula (I) according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene- 4, 4' -diisocyanate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1-10 wt%. The wt% relate to the total CS formulation. ix) Dustable powders (DP, DS)

1-10 wt% of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C) according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%. x) Granules (GR, FG)

0.5-30 wt% of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C) according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or the fluidized bed. xi) Ultra-low volume liquids (UL)

1-50 wt% of a compound of formula (I) or a combination comprising at least one compound of formula (I) (component A) and safeners C (component C) according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.

The formulation types i) to xi) may optionally comprise further auxiliaries, such as 0,1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1-1 wt% anti-foaming agents, and 0,1-1 wt% colorants.

The formulations and/or combinations generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of the compounds of formula (I).

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

Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The formulations in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations, (nach unten verschoben) Methods for applying compounds of formula (I), formulations and /or combinations thereof, on to plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, compounds of formula (I), formulations and /or combinations thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.

Various types of oils, wetting agents, adjuvants, fertilizer, or micronutrients may be added to the compounds of formula (I), the formulations and/or the combinations comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the formulations according to the invention in a weight ratio of 1:100 to 100:1, preferably 1 :10 to 10:1.

The user applies the compounds of formula (I) according to the invention, the formulations and/or the combinations comprising them usually from a pre-dosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the formulation is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the formulation according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

According to one embodiment, either individual components of the formulation according to the invention or partially premixed components, e. g. components comprising compounds of formula (I) and optionally active substances from the group C), may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.

In a further embodiment, individual components of the formulation according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the formulation according to the invention or partially premixed components, e. g components comprising compounds of formula (I) and optionally active substances from the group C), can be applied jointly (e.g. after tank mix) or consecutively.

The compounds of formula (I), are suitable as herbicides.

The compounds of formula (I), or the formulations comprising the compounds of formula (I), control undesired vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

The compounds of the invention are useful for controlling for example following weeds: Abutilon theophrasti (ABUTH), Alopercurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Apera spica-venti (APESV), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinocloa crus-galli (ECHCG), Chenopodium album (CHEAL), Lolium multiflorum (LOLMU), Setaria faberi (SETFA), Setaria viridis (SETVI), to name just a few representative examples.

The compounds of formula (I), or the formulations comprising them, are applied to the plants mainly by spraying the leaves. Here, the application can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (for example from 300 to 400 l/ha). The compounds of formula (I), or the formulations and/or the combinations comprising them, may also be applied by the low-volume or the ultra-low-volume method, or in the form of microgranules.

Application of the compounds of formula (I), or the formulations comprising them, can be done before, during and/or after, preferably during and/or after, the emergence of the undesired vegetation.

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

The compounds of formula (I), or the formulations comprising them, can be applied pre-, post-emergence or preplant, or together with the seed of a crop plant. It is also possible to apply the compounds of formula (I), or the formulations, by applying seed, pretreated with the compounds of formula (I), or the formulations, of a crop plant. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the formulations are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesired vegetation growing underneath, or the bare soil surface (post-directed, lay-by).

In a further embodiment, the compounds of formula (I), or the formulations comprising them, can be applied by treating seed. The treatment of seeds comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of formula (I), or the formulations prepared therefrom.

The term "seed” comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds. The seed used can be seed of the crop plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.

When employed in plant protection, the amounts of active substances applied, i.e. the compounds of formula (I), and, if appropriate, component C without formulation auxiliaries, are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and in particular from 0.1 to 0.75 kg per ha.

In another embodiment of the invention, the application rate of the compounds of formula (I), and, if appropriate, component C, is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.). In another preferred embodiment of the invention, the rates of application of the compounds of formula (I) according to the present invention (total amount of compounds of formula (I)) are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.

In another preferred embodiment of the invention, the application rates of the compounds of formula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.

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

The required application rates of safeners C are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1 .5 kg/h of a.s.

In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.

In another embodiment of the invention, to treat the seed, the amounts of active substances applied, i.e. the compounds of formula (I), and, if appropriate, component C are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.

When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

In case of combinations according to the present invention it is immaterial whether the compounds of formula (I), and/or the component C are formulated and applied jointly or separately.

In the case of separate application, it is of minor importance, in which order the application takes place. It is only necessary, that the compounds of formula (I), and/or the component C are applied in a time frame that allows simultaneous action of the active ingredients on the plants, preferably within a time-frame of at most 14 days, in particular at most 7 days.

Depending on the application method in question, the compounds of formula (I), or the formulations comprising them, can additionally be employed in a further number of crop plants for eliminating undesired vegetation. Examples of suitable crops are the following: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus van napus, Brassica napus van napobrassica, Brassica rapa van silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

Preferred crops are Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus van napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts or permanent crops.

The compounds of formula (I) according to the invention, or the formulations comprising them, can also be used in crops which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.

The term "crops" as used herein includes also (crop) plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.

Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.

Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific "event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.

Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®. However, most of the herbicide tolerance traits have been created via the use of transgenes.

Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.

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

Transgenic corn events comprising herbicide tolerance genes are for example, but not excluding others, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHGOJG, HCEM485, VCO-01981-5, 676, 678, 680, 33121 , 4114, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40- 3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.

Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51 a, 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.

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

Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec, and synthetic variants thereof, like cry1 A, cry 1 Ab, cry1Ab-Ac, crylAc, cry 1 A.105, cry 1 F, cry 1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin have been transferred to other plants. In particular genes coding for protease inhibitors, like CpTI and pinll. A further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes. An example for such a transgene is dvsnf7.

Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt11, Bt176, MON801 , MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121 , 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098.

Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701, MON87751 and DAS-81419.

Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321 , MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Eventl, COT67B, COT102, T303-3, T304-40, GFM Cry1 A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.

Increased yield has been created by increasing ear biomass using the transgene athbl 7, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.

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

Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND- 00410-5.

Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions.

Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art. For example, detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations "International Service for the Acquisition of Agri-biotech Applications (ISAAA)” (http://www.isaaa.org/gmapprovaldatabase) and the "Center for Environmental Risk Assessment (CERA)” (http://cera-gmc.org/GMCropDatabase), as well as in patent applications, like EP3028573 and WC2017/011288.

The use of the compounds of formula (I) or formulations or combinations comprising them according to the invention on crops may result in effects which are specific to a crop comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigor, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).

Furthermore, it has been found that the compounds of formula (I) according to the invention, or the formulations comprising them, are also suitable for the defoliation and/or desiccation of plant parts of crops such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton. In this regard, formulations for the desiccation and/or defoliation of crops, processes for preparing these formulations and methods for desiccating and/or defoliating plants using the compounds of formula (I) have been found.

As desiccants, the compounds of formula (I) are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.

Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pernicious fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.

Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.

A Synthesis Examples

Chemical bonds, drawn as bars in chemical formulae, indicate the relative stereochemistry on the ring system.

Example of the preparation of intermediates (II) and (III)

Methyl (2R)-2-[(3,5-dichlorobenzoyl)amino]propanoate

A solution of 3,5-dichlorobenzoyl chloride (28.3 g, 135 mmol) in dichloromethane (50 ml) was added to a mixture of methyl (2R)-2-aminopropanoate hydrochloride (18.8 g) and triethylamine (27.3 g, 270 mmol) in dichloromethane (250 ml) and stirred for 3 h at room temperature (“RT”). Afterwards, the mixture was washed with hydrochloric acid (200 ml), water (3 x 400 ml) and brine (150 ml). The organic phase was tried over magnesium sulfate and concentrated in vacuo to give the product in quantitative yield. 1 H NMR: (400MHz, deutero-THF) 5 8.1 (1 H), 7.8 (s, 2H), 7.6 (s, 1 H), 4.65 (1 H), 3.65 (s, 3H), 1.45 (d, 3H)

(2R)-2-[(3,5-dichlorobenzoyl)amino]propanoic acid

A solution of methyl (2R)-2-[(3,5-dichlorobenzoyl)amino]propanoate (37.1 g, 134 mmol) was treated with a solution of potassium hydroxide in methanol (1 M, 150 ml) at RT and stirred for 2 h under reflux. Water (100 ml) was added and larger parts of the methanol removed in vacuo. The pH value was adjusted to 1-2 by addition of hydrochloric acid (1 M) which resulted in the formation of a precipitate. Additional water was added and stirring continued for 30 min. Filtration and washing with water yielded the product upon drying at 50°C in a vacuum drying cabinet (33.0g, 94%). 1H NMR: (400MHz, deutero-DMSO) 5 ca. 12.6 (br s, 1 H), 8.9 (1 H), 7.9 (s, 2H), 7.8 (s, 1 H), 4.4 (m, 1 H), 1.4 (m, 3H). Using this saponification method, partial isomerization was observed with varying degrees, depending on the reaction conditions. The following alternative methods are less prone to isomerization:

Saponification alternative 1:

(2R)-2-[(3,5-dichlorobenzoyl)amino]propanoic acid

To a solution of methyl (2R)-2-[(3,5-dichlorobenzoyl)amino]propanoate (3.50 g, 12.7 mmol) in 50 ml dichloromethane was added hydroxy(trimethyl)stannane (4.58 g, 25.4 mmol) and the reaction stirred at reflux for ca. 3 d. The reaction was diluted with additional dichloromethane (50 ml) and aqueous hydrochloric acid solution (1 mol/l, 100 ml) was added. The resulting precipitate was separated by filtration. The remainder was dried at 45°C in vacuo overnight to yield the title compound (2.85 g, 86%). Retention of configuration was confirmed by chiral LC.

(2S)-2-[(3,5-dichlorobenzoyl)amino]propanoic acid

To a solution of methyl (2S)-2-[(3,5-dichlorobenzoyl)amino]propanoate (5.47 g, 19.8 mmol) in 250 ml dichloromethane hydroxy(trimethyl)stannane was added (7.16 g, 39.6 mmol) and the reaction stirred at reflux for 1 d. The reaction was diluted with 200 ml dichloromethane and aqueous hydrochloric acid solution (1 mol/l, 200 ml) added. The resulting precipitate was separated by filtration and washed with dichloromethane and water. The remainder was dried at 45°C in vacuo overnight to yield the title compound (5.1g, 97%).

Saponification alternative 2:

(2R)-2-[(3,5-dichlorobenzoyl)amino]propanoic acid

To a solution of tert-butyl (2R)-2-[(3,5-dichlorobenzoyl)amino]propanoate (19.5 g, 61.3 mmol) in 100 ml dichloromethane was added trifluoro acetic acid (70 g, 10 equivalents) and the reaction mixture stirred at RT for ca. 20 h. The reaction mixture was poured into water (400 ml). The resulting precipitate was separated by filtration and dried at 45°C in vacuo to yield the title compound (15.9 g, 99%).

The precursor tert-butyl ester can for example be prepared according to the following procedure:

Tert-butyl (2S)-2-[(3,5-difluorobenzoyl)amino]propanoate

To a solution of tert-butyl (2S)-2-aminopropanoate hydrochloride (18.1 g, 100 mmol) in 250 ml dichloromethane triethylamine was added at room temperature followed by a solution of 3,5-difluorobenzoyl chloride (17.6 g, 100 mmol) in dichloromethane (50 ml). The reaction mixture was stirred for 2h and then washed with aqueous hydrochloric acid solution (1 mol/l, 150 ml), water (2 x 300 ml) and brine (100 ml) and the organic phase concentrated and dried in vacuo to yield the title compound (27.7 g). 1 H NMR: (400MHz, deutero-DMSO) 5 8.85 (1 H), 7.6 (2H), 7.5 (1 H), 4.35 (1 H), 1.35-1.45 (12H).

Example of the preparation of amino precursors VII

Step 1 :

Methyl (1 S,4R)-4-[[(2R)-2-(tert-butoxycarbonylamino)propanoyl]amino] cyclopent-2-ene-1 -carboxyl ate

To a mixture of (2R)-2-(tert-butoxycarbonylamino)propanoic acid (30.0 g,159 mmol), methyl (1 S,4R)-4- aminocyclopent-2-ene-1-carboxylate hydrochloride (29.6, 166 mmol) and N,N-diisopropylethylamine (61.5 g, 476 mmol) in 200 ml dichloromethane [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylene]-dimethyl-ammonium hexafluorophosphate (HATU, 63.3 g, 166 mmol) was added at RT. The initially formed suspension was heated to reflux and became clear after a couple of minutes and stirring was continued for 2h at the same temperature. After cooling down to RT the organic phase was washed with water (3 x 500 ml), concentrated in vacuo to yield a crude product which was purified by column chromatography to give the title compound in 90% yield. 1 H NMR: (400MHz, DMSO) 5 7.8 (d, 1 H), 6.8 (d, 1 H) 5.9 (m, 1 H), 5.7 (m, 1 H), 4.8 (m, 1 H), 3.95 (m, 1 H), 3.65 (s, 3H), 3.55 (m, 1 H), 2.5 (m, 1 H), 1.75 (m, 1 H), 1.35 (s, 9H), 1.15 (d, 3H).

Step 2:

Methyl (1S,4R)-4-[[(2R)-2-aminopropanoyl]amino]cyclopent-2-ene-1-carboxylate

To a solution of methyl (1S,4R)-4-[[(2R)-2-(tert-butoxycarbonylamino)propanoyl] amino]cyclopent-2-ene-1- carboxylate (90.2 g, 289 mmol) in dichloromethane (250 ml) 2,2,2-trifluoroacetic acid (230 g, 2 mol) was added at room temperature. The reaction mixture was heated under reflux for 1 d. The reaction mixture was carefully quenched with aqueous sodium hydroxide solution (4mol/L, 400 ml) and adjusted to pH 8.5 and extracted with DCM (6 x 200 ml). The combined organic phases were dried in vacuo to yield the product (37.4 g, 61%). (400MHz, DMSO) 5 7.85 (d, 1 H), 5.9 (m, 1 H), 5.75 (m, 1 H), 4.8 (m, 1 H), 3.65 (s, 3H), 3.55 (m, 1 H), 3.2 (m. 1 H), 2.45 (m, 1 H), 1 .8 (br s, 2 H), 1.7 (m, 1 H), 1.1 (d, 3H).

Example 1 (compound 1.3):

Methyl (1S,4R)-4-[[(2R)-2-[(3,5-dichlorobenzoyl)amino]propanoyl]amino]cyclopent-2-ene-1-carboxylate

To a solution of (2R)-2-[(3,5-dichlorobenzoyl)amino]propanoic acid (500 mg, 1.91 mmol), methyl (1S,4R)-4- aminocyclopent-2-ene-1 -carboxylate hydrochloride (390 mg, 2.2 mmol) and HATU (2-(7-aza-1 H-benzotriazole-1-yl)- 1 , 1,3,3-tetramethyluronium hexafluorophosphate, CAS [148893-10-1]), (834 mg, 2.2 mmol) in DMF (6 ml) was added diisopropylethylamine (986 mg, 7.36 mmol). The mixture was stirred at room temperature for 4 h. The solution was treated with ethyl acetate (50 ml) and washed with water (2 x 50 ml). The organic phase was dried over magnesium sulfate and the solvent evaporated under reduced pressure. The crude product was purified by column chromatography to yield 340 mg (46%) product. 1 H NMR: (400MHz, deutero-THF) 5 8.05 (m, 1 H), 7.8 (s, 2H), 7.6 (s, 1 H), 7.4 (m, 1 H), 5.9-5.75 (m, 2H), 4.95 (m, 1 H), 4.55 (m, 1 H), 3.65 (s, 3H), 3.5 (m, 1 H), 2.5 (m, 1 H), 1.8 (m, 1 H), 1.35 (d, 3H)

Alternative preparation of Example 1 (compound 1.3)

To a solution of methyl (1 S,4R)-4-[[(2R)-2-aminopropanoyl]amino]cyclopent-2-ene-1 -carboxylate (4.25 g, 20 mmol) and N-ethyl-N-isopropyl-propan-2-amine (Hiinig base, 5.17 g. 40 mmol) in DCM (80 ml) a solution of 3,5- dichlorobenzoyl chloride (4.40 g, 21.0 mmol) in 20 ml DCM was added over a period of 10 minutes at room temperature and stirring continued for 3.5 h. Afterwards the reaction mixture was treated with an excess of aqueous hydrochloric acid solution (1 mol/l) and washed with water (2x) and brine (1x). The organic phase was concentrated in vacuo. The crude product (8.3 g) was recrystallized from ethyl acetate to yield methyl (1 S,4R)-4-[[(2R)-2-[(3,5- dichlorobenzoyl)amino]propanoyl] amino]cyclopent-2-ene-1-carboxylate as a white solid (5.60 g, 14.5 mmol, 71 %).

Example 2 (compound 1.5):

Methyl (1 S,4R)-4-[[(2R)-2-[(3,5-difluorobenzoyl)amino]propanoyl]amino]cyclopent-2-ene-1-carboxylate

To a solution of (2R)-2-[(3,5-difluorobenzoyl)amino]propanoic acid (500 mg, 2.18 mmol), methyl (1 S,4R)-4- aminocyclopent-2-ene-1 -carboxylate hydrochloride (446 mg, 2.51 mmol) and HATU (2-(7-aza-1 H-benzotriazole-1-yl)- 1 , 1 ,3,3-tetramethyluronium hexafluorophosphate, CAS [148893-10-1]), (954 mg, 2.51 mmol) in DMF (5 ml) was added diisopropylethylamine (564 mg, 4.36 mmol). The mixture was stirred at room temperature for 18 h. The solution was concentrated in vacuo, treated with ethyl acetate and washed with water (2 x 10 ml). The organic phase was dried over magnesium sulfate and the solvent evaporated under reduced pressure. The crude product was purified by column chromatography to yield 350 mg (46%) of the product.

Alternative preparation of Example 2 (compound 1.5)

To a solution of methyl (1 S,4R)-4-[[(2R)-2-aminopropanoyl]amino]cyclopent-2-ene-1 -carboxylate (20.2 g, 95.0 mmol) and N-ethyl-N-isopropyl-propan-2-amine (Hunig base, 24.6 g, 190 mmol) in DCM (200 ml) a solution of 3,5- difluorobenzoyl chloride (17.6 g, 99.8 mmol) in DCM (50 ml) was added at room temperature and stirring continued for 2 h. Afterwards the reaction mixture was treated with an excess of aqueous hydrochloric acid solution (1 mol/l) and washed with water (2x) and brine (1x). The organic phase was concentrated in vacuo. The crude product (37 g) was purified by chromatography to yield methyl (1 S,4R)-4-[[(2R)-2-[(3,5- difluorobenzoyl)amino]propanoyl]amino]cyclopent-2-ene-1 -carboxylate (17.7 g, 53%).

1 H NMR: (400MHz, CDCI₃) 5 7.4 (m, 2H), 7.1 (m, 1 H), 6.95 (m, 1 H), 6.8 (m, 1 H), 5.9 (m, 2H), 5.05 (m, 1 H), 4.65 (m, 1 H), 3.7 (s, 3H), 3.55 (m, 1 H), 2.45 (m, 1 H), 1.9 (m, 1 H), 1.5 (d, 3H)

Example 3 (compound 1.158):

(1 S,4R)-4-[[(2S)-2-[(3,5-difluorobenzoyl)amino]propanoyl]amino]cyclopent-2-ene-1-carboxylic acid

To a solution of methyl (1 S,4R)-4-[[(2S)-2-[(3,5-difluorobenzoyl)amino]propanoyl] amino]cyclopent-2-ene-1- carboxylate (15.1 g, 42.9 mmol) in 250 ml dichloromethane hydroxy(trimethyl)stannane was added (15.5 g, 85.7 mmol) and the reaction stirred at reflux for 4 d. The reaction was diluted with 200 ml dichloromethane and aqueous hydrochloric acid solution (2 mol/l, 150 ml) added. The resulting precipitate was separated by filtration and washed with dichloromethane and plenty of water. The remainder was dried at 45°C in vacuo overnight to yield the title compound (14.2 g, 98%). 1 H NMR: (400MHz, DMSO) 5 ca. 12.4 (br s, 1 H), 8.65 (d, 1 H), 8.1 (d, 1 H) 7.6 (m, 2H), 7.45 (m, 1 H), 5.9 (m, 1 H), 5.75 (m, 1 H), 4.8 (m, 1 H), 4.45 (m, 1 H), 3.45 (m, 1 H), 2.45 (m, 1 H), 1.7 (m, 1 H), 1.35 (d, 3H).

Example 4 (compound 1.93): 3,5-difluoro-N-[(1 S)-1-methyl-2-oxo-2-[[(1 R,4S)-4- (trifluoromethylsulfonylcarbamoyl)cyclopent-2-en-1-yl]amino]ethyl]benzamide

To a solution of (1 S,4R)-4-[[(2S)-2-[(3,5-difluorobenzoyl)amino]propanoyl]amino] cyclopent-2-ene-1 -carboxylic acid (400 mg, 1.18 mmol) in dichloromethane (10 ml) trifluoromethane sulfonamide (194 mg, 1.3 mmol), diisopropylethylamine (458 mg, 3.6 mmol) and HATU (2-(7-aza-1 H-benzotriazole-1-yl)-1, 1 ,3,3-tetramethyluronium hexafluorophosphate, CAS [148893-10-1]), (495 mg, 1.3 mmol) was added and stirred at room temperature for 2h. Dichloromethane (10 ml) was added and the reaction mixture washed with water (2 x 20 ml). The organic phase was separated and dried at 45°C in vacuo overnight and the remainder purified by column chromatography to yield the title compound (260 mg). 1 H NMR: (400MHz, DMSO) 5 8.65 (d, 1 H), 8.1 (d, 1 H) 7.6 (m, 2H), 7.45 (m, 1 H), 5.9 (m, 1 H), 5.7 (m, 1 H), 4.75 (m, 1 H), 4.4 (m, 1 H), 3.45 (m, 1 H), 2.4 (m, 1 H), 1.7 (m, 1 H), 1.3 (d, 3H). In analogy to the examples described above, the following compounds of formula (I), wherein R¹, R⁸ and R⁹ are hydrogen, R⁷ is methyl, and X is oxygen were prepared using commercially available amines. The absolute configuration (R or S) of the chiral carbon atom labeled with is provided.

MZ: is LC-MS-MZ, mass charge ratio; Et = ethyl

In analogy to the examples described above, the following compounds of formula (I), wherein R¹ and R⁸ are hydrogen, and X is oxygen were prepared using commercially available amines. The absolute configuration (R or S) of the chiral carbon atom labeled with is provided.

MZ: is LC-MS-MZ, mass charge ratio; rac. = racemic; Me is methyl. Et is ethyl

In analogy to the examples described above, the following compounds of formula (I), wherein R¹ and R⁸ are hydrogen, R⁷ and R⁹ form, together with the carbon atom to which they are bound, a 3- or 4-membered saturated carbocycle, and X is oxygen were prepared using commercially available amines. The absolute configuration (R or S) of the chiral carbon atom labeled with

is provided.

MZ: is LC-MS-MZ, mass charge ratio;

In analogy to the examples described above, the following compounds of formula (I), wherein R⁷ is methyl, R⁶, R⁸ and R⁹ are hydrogen, and X is oxygen were prepared using commercially available amines. The absolute configuration (R or S) of the chiral carbon atom labeled with is provided.

MZ: is LC-MS-MZ, mass charge ratio; rac. = racemic; Me is methyl;

B Biological examples

The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments: The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the test plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients. For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

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

The test period extended over 2 to 4 weeks. During this time, the test plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the test plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of 70 to < 90 and a very good herbicidal activity is given at values of 90 to 100.

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

At an application rate of 0.063 kg/ha, applied by the post-emergence method:

• compound 1.49 showed good herbicidal activity against ALOMY

• compound 1.61 showed very good herbicidal activity against AMARE

• compound 1.49 showed good herbicidal activity against AVEFA

• compound 1.61 showed good herbicidal activity against CHEAL compound 1.61 showed very good herbicidal activity against ECHCG compound 1.49 showed good herbicidal activity against LOLMU

At an application rate of 0.125 kg/ha, applied by the pre-emergence method:

• compound 1.62 showed good herbicidal activity against ECHCG

• compound 1.62 showed very good herbicidal activity against SETFA

At an application rate of 0.125 kg/ha, applied by the post-emergence method:

• compound 1.62 showed very good herbicidal activity against AMARE

• compounds 1.238, 1.248 showed good herbicidal activity against AMARE

• compound 1.60 showed very good herbicidal activity against AVEFA

• compound 1.62 showed very good herbicidal activity against CHEAL

• compounds 1.62, 1.243 showed very good herbicidal activity against ECHCG

• compound 1.60 showed very good herbicidal activity against LOLMU

• compound 1.60 showed very good herbicidal activity against POLCO

At an application rate of 0.250 kg/ha, applied by the pre-emergence method:

• compounds 1.3, 1.23, 1.242, 1.245, 1.247, 1.256 showed good herbicidal activity against AMARE

• compounds 1.255, 1.258 showed very good herbicidal activity against AMARE

• compounds 1.4, 1.5, 1.106, 1.256 showed very good herbicidal activity against DIGSA

• compound 1.22 showed good herbicidal activity against DIGSA

• compound 1.2 showed good herbicidal activity against LOLMU

• compounds 1.3, 1.4, 1.5, 1.22, 1.24, 1.101, 1.103, 1.106 showed very good herbicidal activity against LOLMU

• compounds 1.3, 1.4, 1.5, 1.22, 1.101, 1.103 showed very good herbicidal activity against SETVI

• compounds 1.23, 1.106 showed good herbicidal activity against SETVI

At an application rate of 0.250 kg/ha, applied by the post-emergence method:

• compounds 1.24, 1.28, 1.101, 1,182, 1.213, 1.254, 1.257, 1.259 showed very good herbicidal activity against ALOMY

• compounds 1.7, 1.21, 1.22, 1.23, 1.26, 1.27, 1.54, 1.188, 1.239 showed good herbicidal activity against ALOMY

• compounds 1.2, 1.3, 1.4, 1.5, 1.64, 1.65, 1.103, 1.106, 1.241, 1.257 showed very good herbicidal activity against AMARE

• compounds 1.42, 1.213, 1.256, 1.259 showed good herbicidal activity against AMARE

• compounds I.2, 1.3, 1.4, 1.5, 1.7, 1.21, 1.22, 1.23, 1.24, 1.28, 1.53, 1.54, 1.64, 1.65, 1.101, 1.103, 1.106, 1.182, 1.213, 1.256, 1.259 showed very good herbicidal activity against AVEFA

• compounds 1.26, 1.27, 1.34, 1.42; 1.183, 1.239, 1.240, 1.254 showed good herbicidal activity against AVEFA

• compounds I.2, 1.3, 1.4, 1.5, 1.7, 1.21, 1.22, 1.24, 1.26, 1.28, 1.64, 1.65, 1.101, 1.103, 1.106, 1.182, 1.257 showed very good herbicidal activity against ECHCG • compounds 1.23, 1.34, 1.42, 1.54; 1.188, 1.254 showed good herbicidal activity against ECHCG

• compound 1.53 showed good herbicidal activity against LOLMU

Comparative assessment of the herbicidal activity of compounds according to the present invention against com- pounds disclosed in WO2023/025854:

The herbicidal activity of the compounds was demonstrated following the same procedures for greenhouse experiments as described herein above.

Comparison 1 : Application rate for each compound: 250 g/ha, applied by post-emergence

Compound according to the invention Compound 1.90 disclosed in Table 1 in

WC2023/025854

Test plants: Herbicidal activity Herbicidal activity

AVEFA 80 35

ECHCG 95 70

Comparison 2: Application rate for each compound: 125 g/ha, applied by post-emergence

Compound according to the invention Compound 1.97 disclosed in Table 1 in

WC2023/025854

Test plants: Herbicidal activity Herbicidal activity

AMARE 70 0

ECHCG 60 0

Claims

1. Compounds of formula (I)

wherein the substituents have the following meanings:

R¹, R⁸ independently of each other are hydrogen, (Ci-C3)-alkyl , (Ci-C3)-haloalkyl , (Cs-C^-cycloalkyl, (C₂-Cs)- alkenyl, (C₂-C3)-haloalkenyl, (Cs-C^-alkynyl, (Cs-C^-haloalkynyl, (Ci-C3)-alkoxy-(Ci-C3)-alkyl, aryl, aryl- (Ci-C3)-alkyl, (Ci-C3)-alkoxy, (Ci-C3)-haloalkoxy, (Ci-C3)-alkoxy-(Ci-C3)-alkoxy, (Ci-C3)-alkylcarbonyl, arylcarbonyl, (Ci-C3)-alkoxycarbonyl, or aryloxycarbonyl;

R², R⁶ independently of each other are hydrogen, halogen, hydroxyl, cyano, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (Ci-C3)-alkoxy or (Ci-C3)-haloalkoxy;

R³, R⁵ independently of each other are hydrogen, halogen, nitro, hydroxyl, cyano, (Ci-C3)-alkyl, (Ci-CsJ-haloal- kyl, (Cs-CsJ-cycloalkyl, (Cs-CsJ-halocycloalkyl, (C₂-C3)-alkenyl, (C₂-C3)-haloalkenyl, (C₂-C3)-alkynyl, (Ci- C3)-alkoxy, (Ci-C3)-haloalkoxy, (Ci-C3)-alkoxycarbonyl, (Ci-C3)-haloalkoxycarbonyl, (Ci-C3)-alkylthio, (Ci-C3)-haloalkylthio, (Ci-C3)-alkylsulfinyl, (Ci-C3)-haloalkylsulfinyl, (Ci-C3)-alkylsulfonyl, (Ci-C3)-haloal- kylsulfonyl, or (Ci-C3)-dialkylamino;

R⁴ is hydrogen, halogen, hydroxyl, cyano, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (C3-C4)-cycloalkyl, (C3-C4)- halocycloalkyl, (Ci-C3)-alkoxy, (Ci-C3)-haloalkoxy, (C₂-C3)-alkenyl, (C₂-C3)-haloalkenyl, (C₂-C3)-alkynyl, (Ci-C3)-dialkylamino or (Ci-C3)-alkylthio;

R⁷ is methyl or ethyl;

R⁹ is hydrogen;

X is oxygen or sulfur;

Q represents the radical of formula (Z-Y),

R¹⁰ is (Ci-C₄)-alkyl;

R¹¹, R¹², R¹³, R¹⁴independently of each other are hydrogen or (Ci-C4)-alkyl; or

R¹⁰ and R¹⁴ form, together with the carbon atoms to which they are bound, a three- to six-membered saturated or partially unsaturated carbocycle or a three- to six-membered saturated or partially unsaturated heterocycle containing 1 or 2 oxygen, nitrogen or sulfur atoms as ring members is CO₂R^e, CONR^bR^h, CONR^eS(O)R^a, CONR^eSO₂R^a, or CONR^b1SO₂NR^b2R^b3; each R^a is independently (Ci-Ce)-alkyl, (Ci-CeJ-haloalkyl, (C3-C4)-alkynyl or (Cs-CeJ-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (Ci-C3)-alkoxy;

R^b is hydrogen or (Ci-C6)-alkyl, (C2-C4)-alkenyl, (C3-C4)-alkynyl, (Cs-CeJ-cycloalkyl, (C3-C6)-cycloalkyl-(Ci- C3)-alkyl, phenyl-(Ci-C3)-alkyl or furanyl-(Ci-C3)-alkyl, where each of the seven last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkoxy, (Ci-C3)-alkylthio, (Ci-C3)-alkylsulfinyl, (Ci-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

R^b1 and R^b2 independently of each other and independently of each occurrence, are hydrogen or have one of the meanings given for R^a;

R^b3 is hydrogen or (Ci-C6)-alkyl, (C2-C4)-alkenyl, (C3-C4)-alkynyl, (Cs-CeJ-cycloalkyl, (C3-C6)-cycloalkyl-(Ci- C3)-alkyl, phenyl-(Ci-C3)-alkyl or furanyl-(Ci-C3)-alkyl, where each of the seven last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, , (Ci-C2)-alkoxy, (Ci-C3)-alkylthio, (Ci-C3)-alkylsulfinyl, (Ci-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; or

R^b2 and R^b3 form, together with the nitrogen atom to which they are bound, a saturated 3-, 4-, 5-, 6- or 7-mem- bered N-bound heterocycle which may contain one further heteroatom or heteroatom group selected from the group consisting of N, 0, S, S(O) and S(O)2 as ring member; each R^e is independently hydrogen or (Ci-C6)-alkyl, (C2-C4)-alkenyl, (C3-C4)-alkynyl, (Cs-CeJ-cycloalkyl, (Cs-Ce)- cycloalkyl-(Ci-C3)-alkyl, phenyl-(Ci-C3)-alkyl or furanyl-(Ci-C3)-alkyl, where each of the seven last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkoxy, (Ci-C2)-haloalkoxy, (Ci-C3)-alkylthio, (Ci-C3)-haloalkylthio, (C1-C3)- alkylsulfinyl, (Ci-C3)-haloalkylsulfinyl, (Ci-C3)-alkylsulfonyl, (Ci-C3)-haloalkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

R^h is hydrogen or (Ci-CeJ-alkyl, (Ci-C2)-alkoxy, (Cs-CeJ-cycloalkyl, (C2-C4)-alkenyl, (Ci-C6)-alkoxycarbonyl- (Ci-C6)-alkyl, or (C3-C4)-alkynyl, where each of the six last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CC>2R^a, (Ci-C2)-alkyl, (C1- C2)-alkoxy and (Ci-C2)-alkoxy-(Ci-C2)-alkoxy; or

R^b and R^h form, together with the nitrogen atom to which they are bound, a saturated 3-, 4-, 5-, 6- or 7-mem- bered N-bound heterocycle which may contain one further heteroatom or heteroatom group selected from the group consisting of N, 0, S, S(O) and S(O)2 as ring member; m is independently of each occurence 0, 1, 2 or 3; n is 1 or 2; including their agriculturally acceptable salts, stereoisomers and tautomers; except for the following compounds:

• (1 R,3S)-3-[[2-[(2,3-Dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid,

• (1 S,3R)-3-[[2-[(3-Nitrobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid,

• (1 S,3R)-3-[[2-[(2,3-Dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid, • 3-[[2-(Benzoylamino)-1-oxopropyl]amino]cyclopentanecarboxylic acid,

• 4-[[2-(Benzoylamino)-1-oxopropyl]amino]cyclohexanecarboxylic acid,

• 4-[[2-(Benzoylamino)-1-oxopropyl]amino]pentanoic acid,

• 4-[[2-[(2,3-Dichlorobenzoyl)amino]-1-oxopropyl]amino]pentanoic acid,

• 4-[[2-[(2-Chlorobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid,

• 4-[[2-[(3-Nitrobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid,

• 4-[[2-[(3-Nitrobenzoyl)amino]-1-oxopropyl]amino]pentanoic acid,

• 4-[[2-[(4-Bromobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid,

• 4-[[2-[(4-Bromobenzoyl)amino]-1-oxopropyl]amino]pentanoic acid,

• 4-[[2-[[4-(1, 1-Dimethylethyl)benzoyl]amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid,

2. The compounds as claimed in claim 1 , wherein

R¹ is hydrogen;

R⁸ is hydrogen.

3. The compounds as claimed in claim 1 or 2, wherein

R² is hydrogen or halogen;

R⁶ is hydrogen, where preferably R² is hydrogen and R⁶ is hydrogen.

4. The compounds as claimed in any one of claims 1 to 3, wherein

R⁵ is hydrogen, halogen, (Ci-C3)-alkyl, (Ci-C3)-haloalkyl, (Ci-C3)-alkoxy or (Ci-C3)-haloalkoxy; where preferably R³ and R⁵, independently of each other, are hydrogen or halogen;

5. The compounds as claimed in any one of claims 1 to 4, wherein

R⁴ is hydrogen or halogen; more preferably hydrogen

6. The compounds as claimed in any one of claims 1 to 5, wherein

R⁷ is methyl.

7. The compounds as claimed in any one of claims 1 to 6, wherein R¹⁰ is methyl.

8. The compounds as claimed in any one of claims 1 to 7, wherein

X is oxygen.

9. The compounds as claimed in any one of claims 1 to 8, wherein

Q is Z-Y selected from the group Z¹-Y to Z⁸-Y;

R^e is hydrogen, (Ci-Ce)-alkyl or (Cs-CeJ-cycloalkyl.

10. Compounds of formula (I.R), wherein R¹ to R⁸, X, and Q are defined as in any of claims 1 to 9, and the stereo- center (#) is in the R-configuration

11. Compounds as claimed in claim 10, wherein

R¹ is hydrogen;

R² is hydrogen or halogen;

R³ is halogen;

R⁴ is hydrogen or halogen;

R⁵ is hydrogen or halogen;

R⁶ is hydrogen;

R⁷ is methyl or ethyl;

R⁸ is hydrogen;

X is oxygen;

Q represents the radical of formula (Z-Y),

R¹¹, R¹², R¹³, R¹⁴ are hydrogen; or

Y Is CO₂R^e;

R^e is hydrogen or (Ci-Ce)-alkyl or (Cs-Cej-cycloalkyl, where each of the two last-mentioned radicals is substituted by m radicals selected from the group consisting of (Ci-C2)-alkoxy, (Ci-Csj-alkylthio, (Ci-Csj-alkylsulfinyl, (Ci-Csj-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; m Is O, 1, or 2; n is 1.

12. A composition comprising at least one compound of formula (I) as defined in any one of claims 1 to 11 , and at least one auxiliary, which is customary for formulating crop protection compounds.

13. The use of a compound of formula (I) as defined in any one of claims 1 to 11, or a composition as claimed in claims 12 for controlling unwanted vegetation.

14. A method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one compound of formula (I) as defined in any one of claims 1 to 11 , or a composition as claimed in claim 12 to act on plants, their seed and/or their habitat.