Herbicidally active bisamides

Abstract

The present invention relates to the compounds of formula (I), wherein the variables are defined as given in the description and claims. The invention further relates to methods of their use and compounds.

Description

[0001] BASF SE 241388

[0002] 1

[0003] Herbicidally active bisamides

[0004] The present invention relates to substituted bisamides as well as to compositions comprising the same. The invention also relates to the use of said substituted bisamides or the corresponding compositions for controlling undesired vegetation. Furthermore, the invention relates to methods for controlling undesired vegetation by using substituted bisamides or the corresponding compositions. Control of undesired vegetation (weeds) is a critical and pressing concern in agricultural practice, impacting crop productivity and overall agricultural sustainability. Weeds compete with crops for essential resources such as water, nutrients and sunlight. Their rapid growth and aggressive nature can significantly reduce crop yields if not adequately controlled. Over time, weeds can develop resistance to herbicides, making them less susceptible to existing chemical control methods. This can render certain herbicides ineffective and limit the options available for weed management.

[0005] Addressing these challenges requires innovative solutions and continuous research and development efforts to enhance weed control strategies while minimizing their impact on the environment and crop productivity. New herbicides that have high activity against and selectivity for target weeds, along with a substantial lack of toxicity for humans and animals, belong to such innovative solutions.

[0006] WO 2001 / 46152 describes diacyl derivatives of propylene diamine and their use as herbicides. The prior art compounds, however, often suffer from insufficient herbicidal activity, in particular at low application rates and / or unsatisfactory selectivity, resulting in a low compatibility with crop plants.

[0007] It is an object of the present invention to provide further herbicidally 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. Further, the compounds should provide weed control over an adequately long period, thus allowing flexible application.

[0008] These and further objectives are achieved by the compounds of formula I defined below includ-ing their agriculturally acceptable salts, stereoisomers and tautomers.

[0009] Accordingly, the present invention relates to compounds of formula I

[0010] R3

[0011] H N N H Z

[0012]

[0013] wherein BASF SE 241388

[0014] 2

[0015] Z is phenyl or 5- or 6- membered heteroaryl containing 1, 2 or 3 heteroatoms independently selected from N, O or S;

[0016] R1each is independently selected from halogen, CN, NO2, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6- alkynyl, Ci-Ce-haloalkyl, C2-Ce-haloalkenyl, C2-Ce-haloalkynyl, C3-Ce-cycloalkyl, C3-Ce-halo- cycloalkyl, C3-Ce-cycloalkoxy, Ci-Ce-alkoxy, C2-Ce-alkenyloxy, C2-Ce-alkynyloxy, Ci-Ce- haloalkoxy, C2-C6-haloalkenyloxy, C2-Ce-haloalkynyloxy, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce- alkoxy-Ci-Ce-alkoxy, Ci-Ce-alkylcarbonyl, Ci-Ce-alkylcarbonyloxy, hydroxycarbonyl, Ci-Ce- alkoxycarbonyl, Ci-Ce-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, NH2, (Ci-Ce-al- kyl)amino, di(Ci-Ce-alkyl)amino, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, C1- Ce-haloalkylthio, Ci-Ce-haloalkylsulfinyl, Ci-Ce-haloalkylsulfonyl, Ci-Ce-alkylaminosulfinyl, di(Ci-C6-alkyl)aminosulfinyl, Ci-Ce-alkylaminosulfonyl, di(Ci-C6-alkyl)aminosulfonyl, halosul- fonyl, phenoxy, phenyl or 4- to 6-membered saturated or unsaturated heterocyclyl having 1, 2 or 3 heteroatoms or heteroatom moieties, selected from O, S, SO, SO2, N or NR12as ring members;

[0017] or two adjacent R1together with the carbon atoms to which they are attached form a fused saturated 5- to 7-membered heterocycle having 1 or 2 heteroatoms or heteroatom moieties, selected from O, S, N or NR12as ring members,

[0018] wherein the aliphatic or aromatic groups of R1or a fused heterocycle are unsubstituted or substituted with 1 or 2 the same or different substituents R11;

[0019] R11is selected from halogen, CN, NO2, NH2, NHR12, NR12R13, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Ci-Ce-haloalkyl, C2-C6-haloalkenyl, C2-Ce-haloalkynyl, Ci-Ce-alkoxy, C2-C6- alkenyloxy, C2-Ce-alkynyloxy, Ci-Ce-haloalkoxy, C2-C6-haloalkenyloxy, C2-C6-haloalkynyloxy or Si(CH3)3;

[0020] R12is selected from Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, C2-Ce-haloal- kenyl, C2-Ce-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-Ce-alkylcarbonyl, Ci-Ce- alkoxycarbonyl, Ci-Ce-alkylaminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, or Ci-Ce-alkylsulfonyl;

[0021] R13is selected from Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, C2-Ce-haloal- kenyl, C2-Ce-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-Ce-alkylcarbonyl, Ci-Ce- alkoxycarbonyl, Ci-Ce-alkylaminocarbonyl, di(Ci-Ce-alkyl)aminocarbonyl, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, or Ci-Ce-alkylsulfonyl;

[0022] n is 0, 1, 2 or 3;

[0023] R2each is independently is selected from halogen, CN, NO2, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-C6- alkynyl, Ci-Ce-haloalkyl, C2-Ce-haloalkenyl, C2-Ce-haloalkynyl, C3-Ce-cycloalkyl, C3-Ce-halo- cycloalkyl, C3-Ce-cycloalkoxy, Ci-Ce-alkoxy, C2-Ce-alkenyloxy, C2-Ce-alkynyloxy, Ci-Ce- haloalkoxy, C2-Ce-haloalkenyloxy, or C2-Ce-haloalkynyloxy;

[0024] wherein the aliphatic groups of R2are unsubstituted or substituted with 1 or 2 the same or different substituents R21; BASF SE 241388

[0025] 5

[0026] R21is selected from halogen, CN, NO2, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloal- kyl, C2-Ce-haloalkenyl, C2-Ce-haloalkynyl, Ci-Ce-alkoxy, C2-Ce-alkenyloxy, C2-Ce-alkynyloxy, Ci-Ce-haloalkoxy, C2-C6-haloalkenyloxy, C2-Ce-haloalkynyloxy or Si(CH₃)₃;

[0027] m is 0, 1, 2 or 3;

[0028] R3is selected from halogen, CN, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, C2- Ce-haloalkenyl, C2-Ce-haloalkynyl, Ci-Ce-alkoxy, C2-Ce-alkenyloxy, C2-Ce-alkynyloxy, Ci-Ce- haloalkoxy, C2-C6-haloalkenyloxy, or C2-Ce-haloalkynyloxy;

[0029] provided that when Z is phenyl bearing substituents R1at the 2- and 3-position with respect to the attachment point of the phenyl to the remainder of the molecule and R1at the 2-position is F, then R1at the 3-position is not OCF3; and

[0030] provided that when Z is phenyl, n = 1, m = 0 and R1is at the 4-position with respect to the attachment point of the phenyl to the remainder of the molecule, then if R1is Br, R3is not Br and if R1is NO2, R3is not NO2

[0031] including their stereoisomers, tautomers and agriculturally accepted salts.

[0032] The term “compounds I” refers to compounds of formula I. Likewise this terminology applies to all subformulae, e.g. “compounds l-A” refer to compounds of formula l-A, etc.

[0033] The compounds I having at least 1 centre of chirality 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 I and their mixtures. The use according to the invention refers to the use of the pure enantiomers or pure diastereomers of the compounds I or to the use of their mixtures. Suitable compounds I also include all possible geometrical stereoisomers (cis / trans isomers) as a specific form of diastereoisomerism 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 “stereoisomers)” encompasses both optical isomers, such as enantiomers or diastereomers existing due to more than 1 stereogenic centre in the molecule, as well as geometrical isomers (cis / trans isomers).

[0034] If the compounds I have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are 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.

[0035] 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 1, 2, 3 or four hydrogen atoms are replaced by Ci-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, heptylammoni-um, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2- BASF SE 241388

[0036] 4

[0037] 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, benzyltrimethylammo-nium, 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)methyla-mine and diethylenetriamine.

[0038] 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.

[0039] Compounds I having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-Ce-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, C₁-C₁₀-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl) methyl) esters and also as thioesters, for example as C₁-C₁₀-alkylthio esters. Preferred mono- and di-Ci-Ce-alkylamides are the methyl and the dimethylamides. Preferred arylamides are, for example, the anilides and the 2-chloroanilides. Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methylhexyl), meptyl (1-methyl heptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester. An example of a straight-chain or branched C₁-C₁₀-alkylthio ester is the ethylthio ester.

[0040] If the compounds I can form tautomers due to intramolecular proton transfer, these tautomers are also encompassed by the definition and comprised in the scope of general formula I according to the invention. Common examples of such interconversions i.a. are keto-enol- (H-O-C=C

[0041] O=C-C-H), thion-thiole- (H-S-C=C S=C-C-H) and amide-imidic acid- (H-N-C=O

[0042] N=C-O-H) tautomerism.

[0043] The amount in which each tautomeric form is present depends on the complete molecular structure and is strongly influenced by the surrounding conditions (presence or absence of solvent, type of solvent, pH, temperature etc.).

[0044] The organic moieties mentioned in the definitions of the variables (substituents) are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cx-Cyindicates in each case the possible number of carbon atoms in the group.

[0045] The term “aryl” denotes an aromatic group having six or ten carbon atoms as ring members. For example, phenyl, 1 -naphthyl, 2-naphthyl.

[0046] The term “heteroaryl” denotes an aromatic group having 5, 6, 8, 9 or 10 ring members which comprises, apart from carbon atoms, 1, 2, 3 or 4 heteroatoms selected from O, S or N. For example, pyrazole, 1,3-thiazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, benzofuran. BASF SE 241388

[0047] 5

[0048] The term “heterocyclyl” denotes a saturated or partially or fully unsaturated mono or bicyclic group having 4 to 10 ring members which comprises apart from carbon atoms 1, 2 or 3 heteroatoms or heteroatom moieties, selected from O, S, SO, SO2, N or NR22or a carbonyl (C(=O)) group as ring members. 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.

[0049] Examples for 4- to 10-membered saturated, partly unsaturated, fully unsaturated or aromatic heterocycles are:

[0050] 4-, 5- or 6-membered monocyclic saturated heterocycle: e.g. 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, azet-idin-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, thiazoli-din-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl, iso-thiazolidin-5-yl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thia-diazolidin-5-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 2-tetrahydropyranyl, 3-tetrahydro-pyranyl, 4- tetrahydropyranyl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, pi-peridin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-1-yl, hexahydro-pyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyrimidin-2-yl, hexahy-dropyrimidin-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 dioxothio-morpholin-3-yl, 1,1-dioxothiomorpholin-4-yl and the like;

[0051] 5- or 6-membered monocyclic partially unsaturated heterocycles: e.g. 2,3-dihydrofuran-2-yl, 2,3-di-hydrofuran-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-iso-thiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothia-zolin-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-dihy-drooxazol-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-thiopy-ran-2-, -3-, -4-, -5- or 6-yl, 2-, 3-, 4-, 5- or6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, BASF SE 241388

[0052] 6

[0053] 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl;

[0054] 5- or 6-membered monocyclic fully unsaturated or aromatic heterocycles: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thia-diazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1.3.4-triazol-2-yl; 5-membered heteroaryl which is attached via nitrogen and contains 1 to 3 nitrogen atoms as ring members, such as pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,3-triazol-1 -yl and 1.2.4-triazol-1-yl; 6-membered heteroaryl, which contains 1, 2 or 3 nitrogen atoms as ring members, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-py-rimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.

[0055] 8-, 9- or 10-membered bicyclic fully unsaturated or aromatic heterocycles: imidazo[5,1-b]thiazol-5-yl, thieno[2,3-d]thiadiazol-6-yl, indol-2-yl, indol-3-yl 1-benzofuran-2-yl, 1-benzothiophen-6-yl, 2-quin-olin-1-yl, 1,3-benzoxazol-2-yl, 1,2,4-benzotriazol-3-yl, pyrazolo[1,5-a]pyrimidin-6-yl, quinazolin-2-yl, quinazolin-6-yl.

[0056] The term "halogen" denotes fluorine, bromine, chlorine or iodine.

[0057] The term "alkyl" denotes a straight-chain or branched saturated hydrocarbon group having usually 1 to 6 carbon atoms (Ci-Ce-alkyl), more frequently 1 to 4 carbon atoms (Ci-C4-alkyl), especially 1 to 3 carbon atoms (Ci-Cs-alkyl) or 1 or 2 carbon atoms (Ci-C2-alkyl). Examples of Ci-Ce-alkyl are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl (= sec-butyl), isobutyl and tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dime-thylpropyl, 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-dime-thylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1, 1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpro-pyl, 1-ethyl-2-methylpropyl and the like.

[0058] The term "alkenyl" denotes an unsaturated straight-chain or branched hydrocarbon group having usually 2 to 6 carbon atoms (C2-Ce-alkenyl), more frequently 2 to 4 carbon atoms (C2-C4-alkenyl) or 2 to 3 carbon atoms (C2-C3-alkenyl) and a double bond in any position. Examples of C2-Ce-alkenyl are 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-bu-tenyl, 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-pen-tenyl, 2-methyl-1-pentenyl, 3-methyl-1 -pentenyl, 4-methyl- 1-pentenyl, 1-methyl-2-pentenyl, 2-me-thyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pen-tenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-me-thyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dime-thyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl- BASF SE 241388

[0059] 7

[0060] 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-tri-methyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like.

[0061] The term "alkynyl" denotes an unsaturated straight-chain or branched hydrocarbon groups having usually 2 to 6 carbon atoms (C2-Ce-alkynyl), more frequently 2 to 4 carbon atoms (C2-C4-alkynyl) or 2 to 3 carbon atoms (C2-C3-alkynyl) and a triple bond in any position. Examples of C2-Ce-alkynyl are 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-me-thyl-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-dime-thyl-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.

[0062] The term "partially or fully halogenated" means that 1 or more, e.g. 1, 2, 3, 4 or 5 or all of the hydrogen atoms of a given chemical group have been replaced by halogen atoms. For example, partially or fully halogenated alkyl is also called haloalkyl.

[0063] The term "haloalkyl" denotes an alkyl group, as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms. Examples of Ci-Ce-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, 1-fluoropro-pyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl and the like.

[0064] The term "haloalkenyl" denotes an alkenyl group, as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms, for example chlorovinyl, chloroallyl and the like. The term "haloalkynyl" denotes an alkynyl group, as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms.

[0065] The term "cycloalkyl" denotes a mono- or bicyclic, saturated cycloaliphatic group having usually 3 to 6 carbon atoms (Cs-Ce-cycloalkyl), more frequently 3 to 5 carbon atoms (Cs-Cs-cycloalkyl) or 3 to 4 carbon atoms (C3-C4-cycloalkyl) as ring members. Examples of Cs-Ce-cycloalkyl are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or bicyclo[2.1.1]hexyl.

[0066] The term "halocycloalkyl" denotes a cycloalkyl group, as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms.

[0067] The term "cycloalkoxy" (O-cycloalkyl) denotes a cycloalkyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. Examples of Cs-Ce-cycloalkoxy are cyclopropoxy, BASF SE 241388

[0068] 8

[0069] cyclobutoxy, cyclopentoxy and cyclohexoxy.

[0070] The term "alkoxy" (O-alkyl) denotes an alkyl group, as defined above, which attached to via an oxygen atom to the remainder of the molecule. Examples of Ci-Ce-alkoxy are methoxy, ethoxy, n-propoxy, 1 -methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy), 1,1 -dimethylethoxy (tert-butoxy), pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methyl-butoxy, 1,1 -di methyl propoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1-methyl pentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1 -dimethylbutoxy, 1,2-dime-thylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1 -ethyl- 1-methylpropoxy or 1-ethyl-2-methylpropoxy and the like.

[0071] The term "alkenyloxy" (O-alkenyl) denotes an alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.

[0072] The term "alkynyloxy" (O-alkynyl) denotes an alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.

[0073] The term "haloalkoxy" (O-haloalkyl) denotes an alkoxy group, as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms. Examples of Ci-Ce-haloalkoxy are OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoro-ethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 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, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobu-toxy, 4-bromobutoxy, nonafluorobutoxy, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodo-pentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy and the like.

[0074] The term "haloalkenyloxy" (O-haloalkenyl) denotes a haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.

[0075] The term "haloalkynyloxy" (O-haloalkynyl) denotes a haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.

[0076] The term “alkoxy-alkyl” (alkyl-O-alkyl) denotes an alkyl group, as defined above, in which 1 hydrogen is replaced by an alkoxy group, as defined above. For example, the term " Ci-Ce-alkoxy-Ci-Ce-alkyl" refers to an alkyl group having 1 to 6 carbon atoms, as defined above, where 1 hydrogen atom is replaced by a Ci-Ce-alkoxy group, as defined above.

[0077] The term "alkoxy-alkoxy" (O-alkyl-O-alkyl) refers to an alkoxy group, as defined above, where 1 hydrogen atom is replaced by another alkoxy group, as defined above. For example, the term " Ci-Ce-alkoxy-Ci-Ce-alkoxy" refers to an alkoxy group having 1 to 6 carbon atoms, as defined above, where 1 hydrogen atom is replaced by a Ci-Ce-alkoxy group, as defined above. Examples are methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, 1 -methoxyethoxy, 1- BASF SE 241388

[0078] 9

[0079] ethoxyethoxy, 1 -propoxyethoxy, 1 -isopropoxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-propoxy-ethoxy, 2-isopropoxyethoxy, 1 -methoxypropoxy, 1 -ethoxypropoxy, 1-propoxypropoxy, 1 -isopropoxypropoxy, 2-methoxypropoxy, 2-ethoxypropoxy, 2-propoxypropoxy, 2-isopropoxypropoxy, 3-meth-oxypropoxy, 3-ethoxypropoxy, 3-propoxypropoxy, 3-isopropoxypropoxy and the like.

[0080] 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.

[0081] The term “alkylcarbonyl” "[C(O)-alkyl] denotes an alkyl group, as defined above, attached via a carbonyl [C(=O)] group to the remainder of the molecule. For example, the term " Ci-Ce-alkylcarbonyl" refers to a Ci-Ce-alkyl group, as defined above, attached via a carbonyl [C(=O)] group to the remainder of the molecule.

[0082] The term “alkylcarbonyloxy” [-OC(=O)-alkyl] denotes an alkyl group, as defined above, attached via a carbonyloxy [-OC(=O)] group to the remainder of the molecule. For example, the term " Ci-Ce-al-kylcarbonyloxy" refers to a Ci-Ce-alkyl group, as defined above, attached via a carbonyloxy group to the remainder of the molecule.

[0083] The term "hydroxycarbonyl" [C(O)OH] denotes a hydroxy group attached via a carbonyl [C(=O)] group to the remainder of the molecule.

[0084] The term "alkoxycarbonyl" [C(O)O-alkyl] denotes an alkoxy group, as defined above, attached via a carbonyl [C(=O)] group to the remainder of the molecule. 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 methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, isobutoxycarbonyl, tert-butoxycarbonyl, pentoxycarbonyl and hexoxycarbonyl and the like.

[0085] The term "alkylamino" denotes an amino group in which 1 hydrogen is replaced by an alkyl group as defined above. Examples of (Ci-Ce-alkyl)amino are methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino or 1,1-dimethylethyla-mino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dime-thylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropyla-mino, 1 -methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutyl-amino 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trime-thylpropylamino,1,2,2-trimethyl-propylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylprop-ylamino and the like.

[0086] The term "di-alkylamino" denotes an amino group in which both hydrogens are replaced by alkyl groups, which may be the same or different, as defined above. Examples of di-(Ci-Ce-alkyl)amino are N, N-dimethylamino, N, N-diethylamino, N, N-di(1-methyl-ethyl)amino, N, N-dipropylamino, N, N-dibutylamino, N, N-di(1-methylpropyl)amino, N, N-di(2-methyl-propyl)amino, N, N-di(1,1-di-methylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propyl-amino, N-methyl-N-(1- BASF SE 241388

[0087] 10

[0088] methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)-amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-di-methylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methyl-ethyl)-N-(1-methyl-pro-pyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-meth-ylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1, 1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethyl-ethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino and the like.

[0089] The term “alkylaminocarbonyl” [C(O)NH-alkyl] denotes an alkylamino group, as defined above, attached via a carbonyl [C(=O)] group to the remainder of the molecule.

[0090] The term “dialkylaminocarbonyl” [C(O)N(alkyl)2] denotes an denotes an alkylamino group, as defined above, attached via a carbonyl [C(=O)] group to the remainder of the molecule.

[0091] The term "alkylthio" (S-alkyl) denotes an alkyl group as, defined above, attached via a sulfur atom to the remainder of the molecule. Examples of Ci-Ce-alkylthio are methylthio, ethylthio, n-propylthio, 1 -methylethylthio (isopropylthio), butylthio, 1 -methylpropylthio (sec-butylthio), 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-methylpen-tylthio, 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 and the like.

[0092] The term "alkylsulfinyl" [S(O)-alkyl] denotes an alkyl group, as defined above, attached via a sulfinyl [S(O)] group to the remainder of the molecule. For example, the term " Ci-Ce-alkylsulfinyl" refers to a Ci-Ce-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. Examples of Ci-Ce-al-kylsulfinyl is methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1 -methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1-methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl), 1, 1-dimethylethylsulfinyl (tert-butylsulfinyl), pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfi-nyl, 3-methylbutylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropyl-sulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1 -methylpentylsulfinyl, 2-methylpentylsulfinyl,

[0093] 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1 -dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfi nyl, 2,2-dimethylbutylsulfinyl, 2, 3-dimethylbutylsulfinyl, 3, 3-di methylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1, 1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfi-nyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl and the like.

[0094] The term "alkylsulfonyl" [S(O)2-alkyl] denotes an alkyl group, as defined above, attached via a sulfonyl [S(O)2] group to the remainder of the molecule. The term " Ci-Ce-alkylsulfonyl" refers to a Ci-Ce-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. Examples of Ci-Ce-alkyl-sulfonyl are methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1 -methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1 -methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl), BASF SE 241388

[0095] 11

[0096] 1.1 -dimethylethylsulfonyl (tert-butylsulfonyl), pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutyl-sulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dime-thylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpen-tylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1, 1-dimethylbutylsulfonyl, 1,2-dimethyl-butylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-di-methylbutylsulfonyl, 1 -ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1, 1,2-trimethylpropylsulfonyl, 1,2,2-tri-methylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.

[0097] The term "haloalkylthio" (S-haloalkyl) refers to an alkylthio group, as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms. Examples of Ci-Ce-haloalkylthio are 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, SC2F5, 2-fluoropropylthio, 3-fluoropropylthio, 2.2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloro-propylthio, 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-bromo-ethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio, nonafluorobutylthio, 5-fluoropen-tylthio, 5-chloropentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohex-ylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio and the like. The term “haloalkylsulfinyl” [S(O)-haloalkyl] denotes a haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group to the remainder of the molecule.

[0098] The term “haloalkylsulfonyl” [S(O)2-haloalkyl] denotes a haloalkyl group, as defined above, attached via a sulfonyl [S(O)2] group to the remainder of the molecule.

[0099] The term “alkylaminosulfinyl” [S(O)-alkylamino] denotes an alkylamino group, as defined above, attached via a sulfinyl [S(O)] group to the remainder of the molecule.

[0100] The term “dialkylaminosulfinyl” [S(O)-dialkylamino] denotes a dialkylamino group, as defined above, attached via a sulfinyl [S(O)] group to the remainder of the molecule.

[0101] The term “alkylaminosulfonyl” [S(O)2-alkylamino] denotes an alkylamino group, as defined above, attached via a sulfonyl [S(O)2] group to the remainder of the molecule.

[0102] The term “dialkylaminosulfonyl” [S(O)2-dialkylamino] denotes a dialkylamino group, as defined above, attached via a sulfonyl [S(O)2] group to the remainder of the molecule.

[0103] The term “halosulfonyl” [S(O)2-halogen] denotes a halogen, as defined above, attached via a sulfonyl [S(O)2] group to the remainder of the molecule.

[0104] The term “phenoxy” denotes a phenyl ring attached via an O atom to the remainder of the molecule.

[0105] In the following, particular embodiments of the compounds I are described. Therein, the meanings of the respective variables (substituents) in the compounds I BASF SE 241388

[0106] 12

[0107]

[0108] are valid on their own as well as in combination with each other.

[0109] According to one embodiment, n is 0. According to another embodiment, n is 1. According to another embodiment, n is 2. According to another embodiment, n is 3.

[0110] When n = 2 or 3, the selection of each of the variables R1is made independent of one another so that R1can be the same or different.

[0111] R1each is preferably independently selected from halogen, CN, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, C2-Ce-haloalkynyl, Cs-Ce-cycloalkyl, Cs-Ce-halocycloalkyl, Cs-Ce-cycloal-koxy, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxy-Ci-Ce-alkoxy, Ci-Ce-alkylcarbonyloxy, (Ci-Ce-alkyl)amino, di(Ci-Ce-alkyl)amino, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, halosulfonyl, phenoxy, phenyl or 4- to 6-membered saturated or unsaturated heterocyclyl having 1, 2 or 3 heteroatoms or heteroatom moieties, selected from O, S, SO, SO2, N or NR12as ring members; or two adjacent R1together with the carbon atoms to which they are attached form a fused saturated 5- to 7-membered heterocycle having 1 or 2 heteroatoms or heteroatom moieties, selected from O, S, N or NR12as ring members, wherein the aliphatic or aromatic groups of R1or a fused heterocycle are unsubstituted or substituted with 1 or 2 substituents R11;

[0112] more preferably R1each is independently selected from halogen, CN, Ci-C4-alkyl, C2-C4- alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2-C4-haloalkynyl, Cs-Ce-cycloalkyl, Cs-Ce-halocyclo- alkyl, Cs-Ce-cycloalkoxy, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkoxy, Ci-C4-alkylcarbonyloxy, (Ci-C4-alkyl)amino, di(Ci-C4-alkyl)amino, C1-C4- alkylsulfinyl, Ci-C4-alkylsulfonyl, halosulfonyl, phenoxy, phenyl or 4- to 6-membered saturated or unsaturated heterocyclyl having 1, 2 or 3 heteroatoms or heteroatom moieties, selected from O, S, SO, SO2, N or NR12as ring members; wherein the aliphatic or aromatic groups of R1are unsubstituted or substituted with 1 or 2 substituents R11;

[0113] even more preferably R1each is independently selected from halogen, CN, Ci-C4-alkyl, C2- C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2-C4-haloalkynyl, Cs-cycloalkyl, Cs-halocycloal- kyl, Cs-cycloalkoxy, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy- Ci-C4-alkoxy, Ci-C4-alkylcarbonyloxy, (Ci-C4-alkyl)amino, di(Ci-C4-alkyl)amino, Ci-C4-alkyl- sulfinyl, Ci-C4-alkylsulfonyl, halosulfonyl, phenoxy, phenyl or 6-membered saturated or unsaturated heterocyclyl having 1 or 2 heteroatoms or heteroatom moieties, selected from O, N or NR12as ring members;

[0114] most preferably R1each is independently selected from F, Cl, Br, I, CN, CH3, C2H5, C3H7, CH(CH3)2, C4H9, C(CH3)3, C≡CH, C≡CCH3, CH2F, CHF2, CF3, C≡CCHF2, C≡CCF3, cyclopropyl, 1-fluorocyclopropyl, 2-fluorocyclopropyl, cyclopropoxy, OCH3, OC2H5, OCH(CH3)2, BASF SE 241388

[0115] 13

[0116] OCH2F, OCHF2, OCF3, CH2OCH3, CH2CH2OCH3, OCH2OCH3, OC(O)CH3, SO2F, SO2CI, OPh, Ph, or morpholin-4-yl;

[0117] in particular R1each is independently selected from F, Cl, Br, CN, C≡CH or OCHF2.

[0118] According to one embodiment, R1is halogen, such as F, Cl, Br or I.

[0119] According to another embodiment, R1is CN.

[0120] According to another embodiment, R1is NO2.

[0121] According to another embodiment, R1is Ci-Ce-alkyl, preferably Ci-C4-alkyl, such as CH3, C2Hs, C3H7, C4H9, CH(CH3)2or C(CH3)3.

[0122] According to another embodiment, R1is C2-Ce-alkenyl, preferably C2-C4-alkenyl, such as CH=CH2, CH2-CH=CH2, CH=CH-CH3, CH(CH3)-CH=CH2or CH2-CH=CH-CH3.

[0123] According to another embodiment, R1is C2-Ce-alkynyl, preferably C2-C4-alkynyl, such as C≡CH, C≡CCH3, CH2C≡CH, C≡CCH2CH3, CH2C≡CCH3or CH2CH2C≡CH.

[0124] According to another embodiment, R1is Ci-Ce-haloalkyl, preferably Ci-C4-haloalkyl, such as CH2F, CHF2, CF3, CH2CH2F, CH2CHF2, CH2CF3, CF2CH2F, CF2CHF2or C2F5.

[0125] According to another embodiment, R1is C2-Ce-haloalkenyl, preferably Ci-C4-haloalkenyl, such as CH=CH2F, CH=CHF2or CH=CF3.

[0126] According to another embodiment, R1is C2-Ce-haloalkynyl, preferably C2-C4-haloalkynyl, such as C≡CCF3, C≡CCHF2, C≡CCH2F, CH2C≡CCF3or CF2C≡CCF3.

[0127] According to another embodiment, R1is C3-C6-cycloalkyl, preferably C3-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0128] According to another embodiment, R1is C3-C6-halocycloalkyl, preferably C3-halocycloalkyl, such as 1-F-cyclopropyl, 1-CI-cyclopropyl, 2-F-cyclopropyl or 2-CI-cyclopropyl.

[0129] According to another embodiment, R1is C3-C6-cycloalkoxy, preferably C3-cycloalkoxy, such as cyclopropoxy.

[0130] According to another embodiment, R1is Ci-Ce-alkoxy, preferably Ci-C4-alkoxy, such as OCH3, OC2H5, OC3H7, OCH(CH3)2, OC4H9, OCH2CH(CH3)2, OCH(CH3)CH2CH3or OC(CH3)3.

[0131] According to another embodiment, R1is C2-Ce-alkenyloxy, preferably C2-C4-alkenyloxy, such as OCH2CH=CH2, OCH2CH2CH=CH2, OCH(CH3)CH=CH2or OCH2CH=CHCH3.

[0132] According to another embodiment, R1is C2-Ce-alkynyloxy, preferably C2-C4-alkynyloxy, such as OCH2C≡CH, OCH2CH2C≡CH, OCH(CH3)C≡CH or OCH2C≡CCH3.

[0133] According to another embodiment, R1is Ci-Ce-haloalkoxy, preferably Ci-C4-haloalkoxy, such as OCH3, OC2H5, OC3H7, OCH(CH3)2, OC4H9, OCH2CH(CH3)2, OCH(CH3)CH2CH3or OC(CH3)3. According to another embodiment, R1is C2-C6-haloalkenyloxy, preferably C2-C4-haloalkenyloxy. According to another embodiment, R1is C2-Ce-haloalkynyloxy, preferably C2-C4-haloalkynyloxy. BASF SE 241388

[0134] 14

[0135] According to another embodiment, R1is Ci-Ce-alkoxy-Ci-Ce-alkyl, preferably Ci-C4-alkoxy-Ci-C4-alkyl, more preferably Ci-C2-alkoxy-Ci-C2-alkyl, such as CH2OCH3, CH2OC2H5, CH2CH2OCH3or CH2CH2OC2H5.

[0136] According to another embodiment, R1is Ci-Ce-alkoxy-Ci-Ce-alkoxy, preferably Ci-C4-alkoxy-Ci-C4-alkoxy, more preferably Ci-C2-alkoxy-Ci-C2-alkoxy, such as OCH2OCH3, OCH2OC2H5, OCH2CH2OCH3, OCH2CH2OC2H5.

[0137] According to another embodiment, R1is Ci-Ce-alkylcarbonyloxy, preferably Ci-C4-alkylcarbonyloxy, such as OC(O)CH3or OC(O)C2H5.

[0138] According to another embodiment, R1is Ci-Ce-alkylcarbonyl, preferably Ci-C4-alkylcarbonyl, such as C(O)CH3, C(O)C2H5, C(O)C3H7, C(O)CH(CH3)2or C(O)C4H9.

[0139] According to another embodiment, R1is hydroxycarbonyl.

[0140] According to another embodiment, R1is Ci-Ce-alkoxycarbonyl, preferably Ci-C4-alkoxycarbonyl, such as C(O)OCH3, C(O)OC2H5or C(O)OC3H7.

[0141] According to another embodiment, R1is Ci-Ce-alkylaminocarbonyl, preferably Ci-C4-alkylaminocar-bonyl, such as C(O)NHCH3, C(O)NHC2H5, C(O)NHC3H7, C(O)NHCH(CH3)2or C(O)NHC4H9.

[0142] According to another embodiment, R1is di(Ci-C6-alkyl)aminocarbonyl, preferably di(Ci-C4-al-kyl)aminocarbonyl, such as C(O)N(CH3)2, C(O)N(C2H5)2, C(O)N(C3H7)2or C(O)N(C4H9)2.

[0143] According to another embodiment, R1is NH2.

[0144] According to another embodiment, R1is (Ci-Ce-alkyl)amino, preferably (Ci-C4-alkyl)amino, such as NHCH3, NHC2H5, NHC3H7, NHCH(CH3)2or NHC4H9.

[0145] According to another embodiment, R1is di(Ci-Ce-alkyl)amino, preferably di(Ci-C4-alkyl)amino, such as N(CH3)2, N(C2H5)2, N(C3H7)2or N(C4H9)2.

[0146] According to another embodiment, R1is Ci-Ce-alkylthio, preferably Ci-C4-alkylthio, such as SCH3, SC2H5or SC3H7.

[0147] According to another embodiment, R1is Ci-Ce-alkylsulfinyl, preferably Ci-C4-alkylsulfinyl, such as S(O)CH3, S(O)C2H5or S(O)C3H7.

[0148] According to another embodiment, R1is Ci-Ce-alkylsulfonyl, preferably Ci-C4-alkylsulfonyl, such as S(O)2CH3, S(O)2C2H5or S(O)2C3H7.

[0149] According to another embodiment, R1is Ci-Ce-haloalkylthio, preferably Ci-C4-haloalkylthio, more preferably Ci-C2-haloalkylthio.

[0150] According to another embodiment, R1is Ci-Ce-haloalkylsulfinyl, preferably Ci -C4-haloalkylsulfi nyl, more preferably Ci-C2-haloalkylsulfinyl.

[0151] According to another embodiment, R1is Ci-Ce-haloalkylsulfonyl, preferably Ci-C4-haloalkylsulfonyl, more preferably Ci-C2-haloalkylsulfonyl.

[0152] According to another embodiment, R1is Ci-Ce-alkylaminosulfinyl, preferably Ci-C4-alkylaminosulfi-nyl, more preferably Ci-C2-alkylaminosulfinyl. BASF SE 241388

[0153] 15

[0154] According to another embodiment, R1is di(Ci-C6-alkyl)aminosulfinyl, preferably di(Ci-C4-alkyl)ami-nosulfinyl, more preferably di(Ci-C2-alkyl)aminosulfinyl.

[0155] According to another embodiment, R1is Ci-Ce-alkylaminosulfonyl, preferably Ci-C4-alkylaminosul-fonyl, more preferably Ci-C2-alkylaminosulfonyl.

[0156] According to another embodiment, R1is di(Ci-C6-alkyl)aminosulfonyl, preferably di(Ci-C4-alkyl)ami-nosulfonyl, more preferably di(Ci-C2-alkyl)aminosulfonyl.

[0157] According to another embodiment, R1is halosulfonyl, such as S(O)2CI.

[0158] According to another embodiment, R1is OPh.

[0159] According to another embodiment, R1is Ph.

[0160] According to another embodiment, R1is 4- to 6-membered saturated or unsaturated heterocyclyl having 1, 2 or 3 heteroatoms or heteroatom moieties, selected from O, S, SO, SO2, N or NR12as ring members, such as oxetan-3-yl, azetidine- 1-yl, azetidine- 3-yl, thietane-3-yl, morpholin-4-yl. According to another embodiment, or two adjacent R1together with the carbon atoms to which they are attached form a fused saturated 5- to 7-membered heterocycle having 1 or 2 heteroatoms or heteroatom moieties, selected from O, S, N or NR12as ring members, preferably a fused saturated 5- membered heterocycle having 1 or 2 heteroatoms or heteroatom moieties, selected from O or N as ring members, more preferably a fused saturated 5- membered heterocycle having 1 O heteroatom as ring member.

[0161] R11is preferably selected from halogen, CN or C2-Ce-alkynyl; more preferably R11is independently selected from F, Cl, Br, CN, C≡CH or C≡CCH3; in particular R11is independently selected from F, CN or C=CH.

[0162] R12is preferably selected from Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-alkylcarbonyl;

[0163] more preferably R12is selected from Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkyl- carbonyl; in particular R12is selected from CH3, C2H5, C(O)CH3.

[0164] R13is preferably selected from Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-alkylcarbonyl;

[0165] more preferably R13is selected from Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-alkyl- carbonyl; in particular R13is selected from CH3, C2H5, C(O)CH3.

[0166] Specific embodiments of R1are listed in the Table R1 below.

[0167] Table R1

[0168] line R1line R1

[0169] R1-1 F R1-10 C4H9

[0170] R1-2 Cl R1-11 CH2CH(CH3)2

[0171] R1-3 Br R1-12 CH(CH3)CH2CH3

[0172] R1-4 I R1-13 C(CH3)3

[0173] R1-5 CN R1-14 CH2CN

[0174] R1-6 CH3R1-15 C≡CH

[0175] R1-7 C2H5 R1-16 C≡CCH3

[0176] R1-8 C3H7 R1-17 CH2C≡CH

[0177]

[0178] R1-9 CH(CH3)2

[0179]

[0180] R1-18 C≡CCH2CH3 BASF SE 241388

[0181] 16

[0182] line R1line R1

[0183] R1-19 CH2C≡CCH3R1-43 OCH3

[0184] R1-20 CH2CH2C≡CH R1-44 OC2H5

[0185] R1-21 CH2F R1-45 OC3H7

[0186] R1-22 CHF2R1-46 OCH(CH3)2

[0187] R1-23 CF3R1-47 OC4H9

[0188] R1-24 C(CH3)F2R1-48 OCH2CH(CH3)2

[0189] R1-25 CH2CH2F R1-49 OCH(CH3)CH2CH3

[0190] R1-26 CH2CHF2R1-50 OC(CH3)3

[0191] R1-27 CH2CF3R1-51 OCH2F

[0192] R1-28 CF2CH2F R1-52 OCHF2

[0193] R1-29 CF2CHF2R1-53 OCF3

[0194] R1-30 C2F5 R1-54 CH2OCH3

[0195] R1-31 cyclopropyl R1-55 CH2OC2H5

[0196] R1-32 cyclobutyl R1-56 CH2CH2OCH3

[0197] R1-33 cyclopentyl R1-57 CH2CH2OC2H5

[0198] R1-34 cyclohexyl R1-58 OC(O)CH3

[0199] R1-35 1-F-cyclopropyl R1-59 OC(O)C2H5

[0200] R1-36 1-CI-cyclopropyl R1-60 S(O)2F

[0201] R1-37 2-F-cyclopropyl R1-61 S(O)2CI

[0202] R1-38 2-CI-cyclopropyl R1-62 Ph

[0203] R1-39 O-cyclopropyl

[0204]

[0205] R1-63 morpholin-4-yl

[0206] R1-40 O-cyclobutyl

[0207] R1-41 O-cyclopentyl

[0208]

[0209] R1-42 O-cyclohexyl

[0210] According to one embodiment, Z is phenyl. According to another embodiment, Z is a 5- or 6-membered heteroaryl containing 1, 2 or 3 heteroatoms independently selected from N, O or S. According to another embodiment, Z is a 5-membered heteroaryl containing 1, 2 or 3 heteroatoms independently selected from N, O or S. According to another embodiment, Z is a 6-mem-bered heteroaryl containing 1, 2 or 3 N atoms.

[0211] Specific embodiments are represented by the structures Z1 to Z20. If the structure contains more than one R1(structures Z5 to Z20), all R1can be the same or different and the selection of each R1is made independent of one another. The wavy line denotes the attachment point of Z to the remainder of the molecule. Each structure Z1 to Z20 corresponds to one particular embodiment of the invention: BASF SE 241388

[0212] 17

[0213]

[0214] According to one embodiment, Z is a 5-membered heteroaryl. According to another embodi-ment, Z is a 6-membered heteroaryl.

[0215] According to one embodiment, the heteroaryl comprises 1 heteroatom selected from N, O or S. According to another embodiment, the heteroaryl comprises 2 heteroatoms independently selected from N, O or S. According to another embodiment, the heteroaryl comprises 3 heteroatoms independently selected from N, O or S.

[0216] According to one embodiment, Z is a 5-membered heteroaryl containing 1 heteroatom selected from N, O or S. According to 1 specific embodiment, the heteroatom is N. According to another specific embodiment, the heteroatom is O. According to another specific embodiment, the heteroatom is S.

[0217] According to another embodiment, Z is a 5-membered heteroaryl containing 2 heteroatoms in-dependently selected from N, O or S. According to 1 specific embodiment, 1 heteroatom is N and the second 1 is O. According to another specific embodiment, 1 heteroatom is N and the second 1 is S. According to another specific embodiment, both heteroatoms are N.

[0218] According to another embodiment, Z is a 5-membered heteroaryl containing 3 heteroatoms independently selected from N, O or S. According to 1 specific embodiment, 2 heteroatoms are N BASF SE 241388

[0219] 18

[0220] and the third 1 is O. According to another specific embodiment, 2 heteroatoms are N and the third 1 is S. According to another specific embodiment, all 3 heteroatoms are N.

[0221] According to one embodiment, Z is a 5-membered heteroaryl and n is 0.

[0222] According to another embodiment, Z is a 5-membered heteroaryl and n is 1.

[0223] According to another embodiment, Z is a 5-membered heteroaryl and n is 2.

[0224] According to another embodiment, Z is a 5-membered heteroaryl and n is 3.

[0225] According to one embodiment, Z is a 6-membered heteroaryl containing 1 N atom as a ring member. According to another embodiment, Z is a 6-membered heteroaryl containing 2 N atoms as ring members. According to another embodiment, Z is a 6-membered heteroaryl containing 3 N atoms as ring members.

[0226] According to one embodiment, Z is a 6-membered heteroaryl and n is 0.

[0227] According to another embodiment, Z is a 6-membered heteroaryl and n is 1.

[0228] According to another embodiment, Z is a 6-membered heteroaryl and n is 2.

[0229] According to another embodiment, Z is a 6-membered heteroaryl and n is 3.

[0230] According to another embodiment, Z is a 6-membered heteroaryl and n is 4.

[0231] According to one embodiment, m is 0. According to another embodiment, m is 1. According to another embodiment, m is 2. According to another embodiment, m is 3. When m = 2 or 3, the selection of the variables R2is made independent of one another so that all R2can be the same or different.

[0232] According to one embodiment, m is 1 and R2is at position 2. According to another embodiment, m is 1 and R2is at position 3. According to another embodiment, m is 2 and R2are at positions 2 and 3. According to another embodiment, m is 2 and R2are at positions 2 and 5. According to another embodiment, m is 2 and R2are at positions 2 and 6. According to another embodiment, m is 2 and R2are at positions 3 and 5. According to another embodiment, m is 3 and R2are at positions 2, 3 and 5. According to another embodiment, m is 3 and R2are at positions 2, 3 and 6.

[0233] R2each is preferably independently selected from halogen, CN, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C2-C6-haloalkenyloxy, C2-C6-haloalkynyloxy; wherein the aliphatic groups of R2are unsubstituted or substituted with 1 or 2 substituents R21;

[0234] more preferably R2each is independently selected from halogen, CN, Ci-C4-alkyl, C2-C4- alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-haloal- kenyloxy or C2-C4-haloalkynyloxy; wherein the aliphatic groups of R2are unsubstituted or substituted with 1 or 2 substituents R21;

[0235] even more preferably R2each is independently selected from F, Cl, Br, CN, CH3, C2H5, C≡CH, C≡CCH3, CH2F, CHF2, CF3, OCH3, OC2H5, OCH2F, OCHF2or OCF3.

[0236] most preferably R2each is independently selected from F, Cl, Br or CN. BASF SE 241388

[0237] 19

[0238] in particular R2each is independently selected from F or Cl.

[0239] According to one embodiment, R2is halogen, such as F, Cl, Br or I.

[0240] According to another embodiment, R2is CN.

[0241] According to another embodiment, R2is NO2.

[0242] According to another embodiment, R2is Ci-Ce-alkyl, preferably Ci-C4-alkyl, such as CH3, C2H5, C3H7, CH(CH3)2, C4H9, CH2CH(CH3)2, CH(CH3)CH2CH3or C(CH3)3.

[0243] According to another embodiment, R2is C2-Ce-alkenyl, preferably C2-C4-alkenyl, such as CH=CH2, CH2-CH=CH2, CH=CH-CH3, CH(CH3)-CH=CH2or CH2-CH=CH-CH3.

[0244] According to another embodiment, R2is C2-Ce-alkynyl, preferably C2-C4-alkynyl, such as C≡CH, C≡CCH3, CH2C≡CH, C≡CCH2CH3, CH2C≡CCH3or CH2CH2C≡CH.

[0245] According to another embodiment, R2is Ci-Ce-haloalkyl, preferably Ci-C4-haloalkyl, such as CH2F, CHF2, CF3, CH2CH2F, CH2CHF2, CH2CF3, CF2CH2F, CF2CHF2or C2F5.

[0246] According to another embodiment, R2is Ci-Ce-haloalkenyl, preferably Ci-C4-haloalkenyl, such as CH=CH2F, CH=CHF2or CH=CF3.

[0247] According to another embodiment, R2is C2-Ce-haloalkynyl, preferably C2-C4-haloalkynyl, such as C≡CCF3, C≡CCHF2, C≡CCH2F, CH2C≡CCF3or CF2C≡CCF3.

[0248] According to another embodiment, R2is Cs-Ce-cycloalkyl, preferably Cs-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0249] According to another embodiment, R2is Cs-Ce-halocycloalkyl, preferably Cs-halocycloalkyl, such as 1-F-cyclopropyl, 1-CI-cyclopropyl, 2-F-cyclopropyl or 2-CI-cyclopropyl.

[0250] According to another embodiment, R2is Cs-Ce-cycloalkoxy, preferably Cs-cycloalkoxy, such as cyclopropoxy.

[0251] According to another embodiment, R2is Ci-Ce-alkoxy, preferably Ci-C4-alkoxy, such as OCH3, OC2H5, OC3H7, OCH(CH3)2, OC4H9, OCH2CH(CH3)2, OCH(CH3)CH2CH3or OC(CH3)3.

[0252] According to another embodiment, R2is C2-Ce-alkenyloxy, preferably C2-C4-alkenyloxy, such as OCH2CH=CH2, OCH2CH2CH=CH2, OCH(CH3)CH=CH2or OCH2CH=CHCH3.

[0253] According to another embodiment, R2is C2-Ce-alkynyloxy, preferably C2-C4-alkynyloxy, such as OCH2C≡CH, OCH2CH2C≡CH, OCH(CH3)C≡CH or OCH2C≡CCH3.

[0254] According to another embodiment, R2is Ci-Ce-haloalkoxy, preferably Ci-C4-haloalkoxy, such as OCH3, OC2H5, OC3H7, OCH(CH3)2, OC4H9, OCH2CH(CH3)2, OCH(CH3)CH2CH3or OC(CH3)3. According to another embodiment, R2is C2-C6-haloalkenyloxy, preferably C2-C4-haloalkenyloxy. According to another embodiment, R2is C2-C6-haloalkynyloxy, preferably C2-C4-haloalkynyloxy. BASF SE 241388

[0255] 20

[0256] R21is preferably selected from Ci-Ce-alkyl, C2-C6-alkenyl, C2-Ce-alkynyl; more preferably from Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl; even more preferably from Ci-C4-alkyl, most preferably from CH3or C2H5.

[0257] Specific embodiments of R2are listed in the Table R2 below.

[0258] Table R2

[0259] line R2

[0260] R2-1 F

[0261] R2-2 Cl

[0262] R2-3 Br

[0263]

[0264] R2-4 I

[0265] R3is preferably selected from halogen, CN, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce- haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C2-C6-haloalkenyloxy or C2-C6-haloalkynyloxy; more preferably R3is selected from halogen, CN, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-al- kynyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-haloalkenyloxy or C2-C4- haloalkynyloxy;

[0266] even more preferably R3is selected from F, Cl, Br, I, CN, CH3, C2H5, C≡CH, C≡CCH3, CH2F, CHF2, CF3, OCH3, OC2H5, OCH2F, OCHF2or OCF3;

[0267] most preferably R3is selected from F, Cl, Br, CN, CH3or C=CH;

[0268] in particular R3is selected from F, Cl, Br, CN, CH3.

[0269] According to one embodiment, R3is halogen, such as F, Cl, Br or I.

[0270] According to another embodiment, R3is CN.

[0271] According to another embodiment, R3is Ci-Ce-alkyl, preferably Ci-C4-alkyl, such as CH3, C2H5, C3H7, CH(CH3)2, C4H9, CH2CH(CH3)2, CH(CH3)CH2CH3or C(CH3)3.

[0272] According to another embodiment, R3is C2-Ce-alkenyl, preferably C2-C4-alkenyl, such as CH=CH2, CH2-CH=CH2, CH=CH-CH3, CH(CH3)-CH=CH2or CH2-CH=CH-CH3.

[0273] According to another embodiment, R3is C2-Ce-alkynyl, preferably C2-C4-alkynyl, such as C≡CH, C≡CCH3, CH2C≡CH, C≡CCH2CH3, CH2C≡CCH3or CH2CH2C≡CH.

[0274] According to another embodiment, R3is Ci-Ce-haloalkyl, preferably Ci-C4-haloalkyl, such as CH2F, CHF2, CF3, CH2CH2F, CH2CHF2, CH2CF3, CF2CH2F, CF2CHF2or C2F5.

[0275] According to another embodiment, R3is Ci-Ce-haloalkenyl, preferably Ci-C4-haloalkenyl, such as CH=CH2F, CH=CHF2or CH=CF3.

[0276] According to another embodiment, R3is C2-Ce-haloalkynyl, preferably C2-C4-haloalkynyl, such as C≡CCF3, C≡CCHF2, C≡CCH2F, CH2C≡CCF3or CF2C≡CCF3.

[0277] According to another embodiment, R3is Ci-Ce-alkoxy, preferably Ci-C4-alkoxy, such as OCH3, OC2H5, OC3H7, OCH(CH3)2, OC4H9, OCH2CH(CH3)2, OCH(CH3)CH2CH3or OC(CH3)3. BASF SE 241388

[0278] 21

[0279] According to another embodiment, R3is C2-Ce-alkenyloxy, preferably C2-C4-alkenyloxy, such as OCH2CH=CH2, OCH2CH2CH=CH2, OCH(CH3)CH=CH2or OCH2CH=CHCH3.

[0280] According to another embodiment, R3is C2-Ce-alkynyloxy, preferably C2-C4-alkynyloxy, such as OCH2C≡CH, OCH2CH2C≡CH, OCH(CH3)C≡CH or OCH2C≡CCH3.

[0281] According to another embodiment, R3is Ci-Ce-haloalkoxy, preferably Ci-C4-haloalkoxy, such as OCH3, OC2H5, OC3H7, OCH(CH3)2, OC4H9, OCH2CH(CH3)2, OCH(CH3)CH2CH3or OC(CH3)3. According to another embodiment, R3is C2-Ce-haloalkenyloxy, preferably C2-C4-haloalkenyloxy. According to another embodiment, R3is C2-Ce-haloalkynyloxy, preferably C2-C4-haloalkynyloxy.

[0282] Specific embodiments of R3are listed in the Table R3 below.

[0283] Table R3

[0284] line R3line R3

[0285] R3-1 F R3-7 C2H5

[0286] R3-2 Cl R3-8 C3H7

[0287] R3-3 Br R3-9 CH(CH3)2

[0288] R3-4 I R3-10 C4H9

[0289] R3-5 CN R3-11 CH2CH(CH3)2

[0290]

[0291] R3-6 CH3

[0292]

[0293] R3-12 CH(CH3)CH2CH3

[0294] Preferred are compounds I, wherein

[0295] Z is phenyl;

[0296] R1each is independently selected from is halogen, CN, Ci-Ce-alkyl, C2-C4-alkynyl, Ci-Ce- haloalkyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkoxy, Ci-Ce-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-Ce-alkylcarbonyloxy, halosulfonyl, phenyl or 6- membered saturated or unsaturated heterocyclyl having 1 or 2 heteroatoms selected from O, S or N as ring members;

[0297] wherein the aliphatic or aromatic groups of R1are unsubstituted or substituted with 1 substituent R11;

[0298] R11is CN;

[0299] n is 2 or 3; preferably 2;

[0300] R2is halogen, preferably F or Cl;

[0301] m is 0, 1, 2 or 3; preferably 0, 1 or 2;

[0302] R3is halogen, CN or Ci-Ce-alkyl; preferably F, Cl or CN.

[0303] provided that if R1at the 2-position of the phenyl ring (Z) is F, then R1at the 3-position of the phenyl ring (Z) is not OCF3; BASF SE 241388

[0304] 22

[0305] In one embodiment, the compounds I are present in form of a racemic mixture of compounds I-R and l-S:

[0306]

[0307] In another embodiment, the compound l-R with the R-configuration at the tertiary carbon atom of the propylene diamine moiety is present in an amount of more than 50% by weight, in particular of at least 70% by weight, more particularly of at least 85% by weight, specifically of at least 90% by weight, especially of at least 95% by weight, based on the total weight of compounds I-R and l-S.

[0308] In another embodiment, the compound l-S with the S-configuration at the tertiary carbon atom of the propylene diamine moiety is present in an amount of more than 50% by weight, in particular of at least 70% by weight, more particularly of at least 85% by weight, specifically of at least 90% by weight, especially of at least 95% by weight based on the total weight of compounds l-R and l-S.

[0309] In one specific embodiment, the compounds I are present as a pure compound l-R.

[0310] In another specific embodiment, the compounds I are present as a pure compound l-S.

[0311] According to specific embodiments, compounds of formula I are represented by the compounds of formula l-A, l-R-A and l-S-A, wherein the variables R1, R2, R3, m and n are as defined above. The selection of each of the variables (R2)mand (R1)nis made independent of one another.

[0312]

[0313] BASF SE 241388

[0314] 23

[0315] Particular preference is given to compounds, l-A, l-R-A and l-S-A having R1as defined in Table T1.

[0316] Table T1

[0317] line R1line R1

[0318] T1-1 - T1-45 2-cyclopropyl, 3-Br

[0319] T1-2 2-F T1-46 2-cyclopropyl, 3-CeCH

[0320] T1-3 2-CI T1-47 2-cyclopropyl, 3-Ph

[0321] T1-4 2-Br T1-48 2-cyclopropyl, 3-CH3

[0322] T1-5 2-cyclopropyl T1-49 2-CeCH, 3-F

[0323] T1-6 2-CECH T1-50 2-CECH, 3-CI

[0324] T1-7 2-Ph T1-51 2-CeCH, 3-Br

[0325] T1-8 2-CH3T1-52 2-CeCH, 3-cyclopropyl

[0326] T1-9 3-F T1-53 2-CeCH, 3-Ph

[0327] T1-10 3-CI T1-54 2-CeCH, 3-CH3

[0328] T1-11 3-Br T1-55 2-Ph, 3-F

[0329] T1-12 3-cyclopropyl T1-56 2-Ph, 3-CI

[0330] T1-13 3-CeCH T1-57 2-Ph, 3-Br

[0331] T1-14 3-Ph T1-58 2-Ph, 3-cyclopropyl

[0332] T1-15 3-CH3 T1-59 2-Ph, 3-CeCH

[0333] T1-16 4-F T1-60 2-Ph, 3-CH3

[0334] T1-17 4-CI T1-61 2-CH3, 3-F

[0335] T1-18 4-Br T1-62 2-CH3, 3-CI

[0336] T1-19 4-cyclopropyl T1-63 2-CH3, 3-Br

[0337] T1-20 4-CeCH T1-64 2-CH3, 3-cyclopropyl

[0338] T1-21 4-Ph T1-65 2-CH3, 3-CeCH

[0339] T1-22 4-CH3 T1-66 2-CH3, 3-Ph

[0340] T1-23 2-F, 3-F T1-67 2-F, 4-F

[0341] T1-24 2-F, 3-CI T1-68 2-F, 4-CI

[0342] T1-25 2-F, 3-Br T1-69 2-F, 4-Br

[0343] T1-26 2-F, 3-cyclopropyl T1-70 2-F, 4-cyclopropyl

[0344] T1-27 2-F, 3-CeCH T1-71 2-F, 4-CeCH

[0345] T1-28 2-F, 3-Ph T1-72 2-F, 4-Ph

[0346] T1-29 2-F, 3-CH3 T1-73 2-F, 4-CH3

[0347] T1-30 2-CI, 3-F T1-74 2-CI, 4-F

[0348] T1-31 2-CI, 3-CI T1-75 2-CI, 4-CI

[0349] T1-32 2-CI, 3-Br T1-76 2-CI, 4-Br

[0350] T1-33 2-CI, 3-cyclopropyl T1-77 2-CI, 4-cyclopropyl

[0351] T1-34 2-CI, 3-CeCH T1-78 2-CI, 4-CeCH

[0352] T1-35 2-CI, 3-Ph T1-79 2-CI, 4-Ph

[0353] T1-36 2-CI, 3-CH3 T1-80 2-CI, 4-CH3

[0354] T1-37 2-Br, 3-F T1-81 2-Br, 4-F

[0355] T1-38 2-Br, 3-CI T1-82 2-Br, 4-CI

[0356] T1-39 2-Br, 3-cyclopropyl T1-83 2-Br, 4-cyclopropyl

[0357] T1-40 2-Br, 3-CeCH T1-84 2-Br, 4-CeCH

[0358] T1-41 2-Br, 3-Ph T1-85 2-Br, 4-Ph

[0359] T1-42 2-Br, 3-CH3 T1-86 2-Br, 4-CH3

[0360] T1-43 2-cyclopropyl, 3-F T1-87 2-cyclopropyl, 4-F

[0361]

[0362] T1-44 2-cyclopropyl, 3-CI T1-88 2-cyclopropyl, 4-CI BASF SE 241388

[0363] 24

[0364] line R1line R1

[0365] T1-89 2-cyclopropyl, 4-Br T1-138 3-F, 4-F

[0366] T1-90 2-cyclopropyl, 4-CECH T1-139 3-F, 4-CI

[0367] T1-91 2-cyclopropyl, 4-Ph T1-140 3-F, 4-Br

[0368] T1-92 2-cyclopropyl, 4-CHs T1-141 3-F, 4-cyclopropyl T1-93 2-CECH, 4-F T1-142 3-F, 4-CECH

[0369] T1-94 2-CECH, 4-CI T1-143 3-F, 4-Ph

[0370] T1-95 2-CECH, 4-Br T1-144 3-F, 4-CH3

[0371] T1-96 2-CECH, 4-cyclopropyl T1-145 3-CI, 4-F

[0372] T1-97 2-CECH, 4-Ph T1-146 3-CI, 4-CI

[0373] T1-98 2-CECH, 4-CH3T1-147 3-CI, 4-Br

[0374] T1-99 2-Ph, 4-F T1-148 3-CI, 4-cyclopropyl T1-100 2-Ph, 4-CI T1-149 3-CI, 4-CECH

[0375] T1-101 2-Ph, 4-Br T1-150 3-CI, 4-Ph

[0376] T1-102 2-Ph, 4-cyclopropyl T1-151 3-CI, 4-CH3

[0377] T1-103 2-Ph, 4-CECH T1-152 3-Br, 4-F

[0378] T1-104 2-Ph, 4-CH3 T1-153 3-Br, 4-CI

[0379] T1-105 2-CH3, 4-F T1-154 3-Br, 4-cyclopropyl T1-106 2-CH3, 4-CI T1-155 3-Br, 4-CECH

[0380] T1-107 2-CH3, 4-Br T1-156 3-Br, 4-Ph

[0381] T1-108 2-CH3, 4-cyclopropyl T1-157 3-Br, 4-CH3

[0382] T1-109 2-CH3, 4-CECH T1-158 3-cyclopropyl, 4-F T1-110 2-CH3, 4-Ph T1-159 3-cyclopropyl, 4-CI T1-111 2-F, 5-F T1-160 3-cyclopropyl, 4-Br T1-112 2-F, 5-CI T1-161 3-cyclopropyl, 4-CECH T1-113 2-CI, 5-F T1-162 3-cyclopropyl, 4-Ph T1-114 2-CI, 5-CI T1-163 3-cyclopropyl, 4-CH3 T1-115 2-Br, 5-F T1-164 3-CECH, 4-F

[0383] T1-116 2-Br, 5-CI T1-165 3-CECH, 4-CI T1-117 2-cyclopropyl, 5-F T1-166 3-CECH, 4-Br T1-118 2-cyclopropyl, 5-CI T1-167 3-CECH, 4-cyclopropyl T1-119 2-CECH, 5-F T1-168 3-CECH, 4-Ph T1-120 2-CECH, 5-CI T1-169 3-CECH, 4-CH3 T1-121 2-Ph, 5-F T1-170 3-Ph, 4-F

[0384] T1-122 2-Ph, 5-CI T1-171 3-Ph, 4-CI

[0385] T1-123 2-CH3, 5-F T1-172 3-Ph, 4-Br

[0386] T1-124 2-CH3, 5-CI T1-173 3-Ph, 4-cyclopropyl T1-125 2-F, 6-F T1-174 3-Ph, 4-CECH T1-126 2-F, 6-CI T1-175 3-Ph, 4-CH3

[0387] T1-127 2-CI, 6-CI T1-176 3-CH3, 4-F

[0388] T1-128 2-Br, 6-F T1-177 3-CH3, 4-CI

[0389] T1-129 2-Br, 6-CI T1-178 3-CH3, 4-Br

[0390] T1-130 2-cyclopropyl, 6-F T1-179 3-CH3, 4-cyclopropyl T1-131 2-cyclopropyl, 6-CI T1-180 3-CH3, 4-CECH T1-132 2-CECH, 6-F T1-181 3-CH3, 4-Ph

[0391] T1-133 2-CECH, 6-CI T1-182 3-F, 5-F

[0392] T1-134 2-Ph, 6-F T1-183 3-F, 5-CI

[0393] T1-135 2-Ph, 6-CI T1-184 3-CI, 5-CI

[0394] T1-136 2-CH3, 6-F T1-185 3-Br, 5-F

[0395]

[0396] T1-137 2-CH3, 6-CI

[0397]

[0398] T1-186 3-Br, 5-CI BASF SE 241388

[0399] 25

[0400] line R1line R1

[0401] T1-187 3-cyclopropyl, 5-F T1-236 2-F, 3-CH3, 4-cyclopropyl T1-188 3-cyclopropyl, 5-CI T1-237 2-F, 3-CH3, 4-CECH T1-189 3-CECH, 5-F T1-238 2-F, 3-CH3, 4-Ph

[0402] T1-190 3-CECH, 5-CI T1-239 2-CI, 3-F, 4-F

[0403] T1-191 3-Ph, 5-F T1-240 2-CI, 3-F, 4-CI

[0404] T1-192 3-Ph, 5-CI T1-241 2-CI, 3-F, 4-Br

[0405] T1-193 3-CH3, 5-F T1-242 2-CI, 3-F, 4-cyclopropyl T1-194 3-CH3, 5-CI T1-243 2-CI, 3-F, 4-CECH

[0406] T1-195 2-F, 3-F, 4-F T1-244 2-CI, 3-F, 4-Ph

[0407] T1-196 2-F, 3-F, 4-CI T1-245 2-CI, 3-F, 4-CH3

[0408] T1-197 2-F, 3-F, 4-Br T1-246 2-CI, 3-CI, 4-F

[0409] T1-198 2-F, 3-F, 4-cyclopropyl T1-247 2-CI, 3-CI, 4-CI

[0410] T1-199 2-F, 3-F, 4-CECH T1-248 2-CI, 3-CI, 4-Br

[0411] T1-200 2-F, 3-F, 4-Ph T1-249 2-CI, 3-CI, 4-cyclopropyl T1-201 2-F, 3-F, 4-CH3 T1-250 2-CI, 3-CI, 4-CECH

[0412] T1-202 2-F, 3-CI, 4-F T1-251 2-CI, 3-CI, 4-Ph

[0413] T1-203 2-F, 3-CI, 4-CI T1-252 2-CI, 3-CI, 4-CH3

[0414] T1-204 2-F, 3-CI, 4-Br T1-253 2-CI, 3-Br, 4-F

[0415] T1-205 2-F, 3-CI, 4-cyclopropyl T1-254 2-CI, 3-Br, 4-CI

[0416] T1-206 2-F, 3-CI, 4-CECH T1-255 2-CI, 3-Br, 4-cyclopropyl T1-207 2-F, 3-CI, 4-Ph T1-256 2-CI, 3-Br, 4-CECH

[0417] T1-208 2-F, 3-CI, 4-CH3 T1-257 2-CI, 3-Br, 4-Ph

[0418] T1-209 2-F, 3-Br, 4-F T1-258 2-CI, 3-Br, 4-CH3

[0419] T1-210 2-F, 3-Br, 4-CI T1-259 2-CI, 3-cyclopropyl, 4-F T1-211 2-F, 3-Br, 4-cyclopropyl T1-260 2-CI, 3-cyclopropyl, 4-CI T1-212 2-F, 3-Br, 4-CECH T1-261 2-CI, 3-cyclopropyl, 4-Br T1-213 2-F, 3-Br, 4-Ph T1-262 2-CI, 3-cyclopropyl, 4-CECH T1-214 2-F, 3-Br, 4-CH3 T1-263 2-CI, 3-cyclopropyl, 4-Ph T1-215 2-F, 3-cyclopropyl, 4-F T1-264 2-CI, 3-cyclopropyl, 4-CH3 T1-216 2-F, 3-cyclopropyl, 4-CI T1-265 2-CI, 3-CECH, 4-F

[0420] T1-217 2-F, 3-cyclopropyl, 4-Br T1-266 2-CI, 3-CECH, 4-CI T1-218 2-F, 3-cyclopropyl, 4-CECH T1-267 2-CI, 3-CECH, 4-Br T1-219 2-F, 3-cyclopropyl, 4-Ph T1-268 2-CI, 3-CECH, 4-cyclopropyl T1-220 2-F, 3-cyclopropyl, 4-CH3 T1-269 2-CI, 3-CECH, 4-Ph T1-221 2-F, 3-CECH, 4-F T1-270 2-CI, 3-CECH, 4-CH3 T1-222 2-F, 3-CECH, 4-CI T1-271 2-CI, 3-Ph, 4-F

[0421] T1-223 2-F, 3-CECH, 4-Br T1-272 2-CI, 3-Ph, 4-CI

[0422] T1-224 2-F, 3-CECH, 4-cyclopropyl T1-273 2-CI, 3-Ph, 4-Br

[0423] T1-225 2-F, 3-CECH, 4-Ph T1-274 2-CI, 3-Ph, 4-cyclopropyl T1-226 2-F, 3-CECH, 4-CH3 T1-275 2-CI, 3-Ph, 4-CECH T1-227 2-F, 3-Ph, 4-F T1-276 2-CI, 3-Ph, 4-CH3

[0424] T1-228 2-F, 3-Ph, 4-CI T1-277 2-CI, 3-CH3, 4-F

[0425] T1-229 2-F, 3-Ph, 4-Br T1-278 2-CI, 3-CH3, 4-CI

[0426] T1-230 2-F, 3-Ph, 4-cyclopropyl T1-279 2-CI, 3-CH3, 4-Br

[0427] T1-231 2-F, 3-Ph, 4-CECH T1-280 2-CI, 3-CH3, 4-cyclopropyl T1-232 2-F, 3-Ph, 4-CH3 T1-281 2-CI, 3-CH3, 4-CECH T1-233 2-F, 3-CH3, 4-F T1-282 2-CI, 3-CH3, 4-Ph

[0428] T1-234 2-F, 3-CH3, 4-CI T1-283 2-Br, 3-F, 4-F

[0429]

[0430] T1-235 2-F, 3-CH3, 4-Br

[0431]

[0432] T1-284 2-Br, 3-F, 4-CI BASF SE 241388

[0433] 26

[0434] line R1line R1

[0435] T1-285 2-Br, 3-F, 4-cyclopropyl T1-334 2-cyclopropyl, 3-CECH, 4-Br T1-286 2-Br, 3-F, 4-CECH T1-335 2-cyclopropyl, 3-CECH, 4-Ph T1-287 2-Br, 3-F, 4-Ph T1-336 2-cyclopropyl, 3-CECH, 4-CH3 T1-288 2-Br, 3-F, 4-CH3T1-337 2-cyclopropyl, 3-Ph, 4-F T1-289 2-Br, 3-CI, 4-F T1-338 2-cyclopropyl, 3-Ph, 4-CI T1-290 2-Br, 3-CI, 4-CI T1-339 2-cyclopropyl, 3-Ph, 4-Br T1-291 2-Br, 3-CI, 4-cyclopropyl T1-340 2-cyclopropyl, 3-Ph, 4-CECH T1-292 2-Br, 3-CI, 4-CECH T1-341 2-cyclopropyl, 3-Ph, 4-CH3 T1-293 2-Br, 3-CI, 4-Ph T1-342 2-cyclopropyl, 3-CH3, 4-F T1-294 2-Br, 3-CI, 4-CH3 T1-343 2-cyclopropyl, 3-CH3, 4-CI T1-295 2-Br, 3-cyclopropyl, 4-F T1-344 2-cyclopropyl, 3-CH3, 4-Br T1-296 2-Br, 3-cyclopropyl, 4-CI T1-345 2-cyclopropyl, 3-CH3, 4-CECH T1-297 2-Br, 3-cyclopropyl, 4-CECH T1-346 2-cyclopropyl, 3-CH3, 4-Ph T1-298 2-Br, 3-cyclopropyl, 4-Ph T1-347 2-CECH, 3-F, 4-F

[0436] T1-299 2-Br, 3-cyclopropyl, 4-CH3 T1-348 2-CECH, 3-F, 4-CI

[0437] T1-300 2-Br, 3-CECH, 4-F T1-349 2-CECH, 3-F, 4-Br

[0438] T1-301 2-Br, 3-CECH, 4-CI T1-350 2-CECH, 3-F, 4-cyclopropyl T1-302 2-Br, 3-CECH, 4-cyclopropyl T1-351 2-CECH, 3-F, 4-Ph

[0439] T1-303 2-Br, 3-CECH, 4-Ph T1-352 2-CECH, 3-F, 4-CH3

[0440] T1-304 2-Br, 3-CECH, 4-CH3T1-353 2-CECH, 3-CI, 4-F

[0441] T1-305 2-Br, 3-Ph, 4-F T1-354 2-CECH, 3-CI, 4-CI

[0442] T1-306 2-Br, 3-Ph, 4-CI T1-355 2-CECH, 3-CI, 4-Br

[0443] T1-307 2-Br, 3-Ph, 4-cyclopropyl T1-356 2-CECH, 3-CI, 4-cyclopropyl T1-308 2-Br, 3-Ph, 4-CECH T1-357 2-CECH, 3-CI, 4-Ph

[0444] T1-309 2-Br, 3-Ph, 4-CH3 T1-358 2-CECH, 3-CI, 4-CH3 T1-310 2-Br, 3-CH3, 4-F T1-359 2-CECH, 3-Br, 4-F

[0445] T1-311 2-Br, 3-CH3, 4-CI T1-360 2-CECH, 3-Br, 4-CI

[0446] T1-312 2-Br, 3-CH3, 4-cyclopropyl T1-361 2-CECH, 3-Br, 4-cyclopropyl T1-313 2-Br, 3-CH3, 4-CECH T1-362 2-CECH, 3-Br, 4-Ph

[0447] T1-314 2-Br, 3-CH3, 4-Ph T1-363 2-CECH, 3-Br, 4-CH3T1-315 2-cyclopropyl, 3-F, 4-F T1-364 2-CECH, 3-cyclopropyl, 4-F T1-316 2-cyclopropyl, 3-F, 4-CI T1-365 2-CECH, 3-cyclopropyl, 4-CI T1-317 2-cyclopropyl, 3-F, 4-Br T1-366 2-CECH, 3-cyclopropyl, 4-Br T1-318 2-cyclopropyl, 3-F, 4-CECH T1-367 2-CECH, 3-cyclopropyl, 4-Ph T1-319 2-cyclopropyl, 3-F, 4-Ph T1-368 2-CECH, 3-cyclopropyl, 4-CH3 T1-320 2-cyclopropyl, 3-F, 4-CH3 T1-369 2-CECH, 3-Ph, 4-F

[0448] T1-321 2-cyclopropyl, 3-CI, 4-F T1-370 2-CECH, 3-Ph, 4-CI

[0449] T1-322 2-cyclopropyl, 3-CI, 4-CI T1-371 2-CECH, 3-Ph, 4-Br

[0450] T1-323 2-cyclopropyl, 3-CI, 4-Br T1-372 2-CECH, 3-Ph, 4-cyclopropyl T1-324 2-cyclopropyl, 3-CI, 4-CECH T1-373 2-CECH, 3-Ph, 4-CH3 T1-325 2-cyclopropyl, 3-CI, 4-Ph T1-374 2-CECH, 3-CH3, 4-F

[0451] T1-326 2-cyclopropyl, 3-CI, 4-CH3 T1-375 2-CECH, 3-CH3, 4-CI T1-327 2-cyclopropyl, 3-Br, 4-F T1-376 2-CECH, 3-CH3, 4-Br T1-328 2-cyclopropyl, 3-Br, 4-CI T1-377 2-CECH, 3-CH3, 4-cyclopropyl T1-329 2-cyclopropyl, 3-Br, 4-CECH T1-378 2-CECH, 3-CH3, 4-Ph T1-330 2-cyclopropyl, 3-Br, 4-Ph T1-379 2-Ph, 3-F, 4-F

[0452] T1-331 2-cyclopropyl, 3-Br, 4-CH3 T1-380 2-Ph, 3-F, 4-CI

[0453] T1-332 2-cyclopropyl, 3-CECH, 4-F T1-381 2-Ph, 3-F, 4-Br

[0454]

[0455] T1-333 2-cyclopropyl, 3-CECH, 4-CI

[0456]

[0457] T1-382 2-Ph, 3-F, 4-cyclopropyl BASF SE 241388

[0458] 27

[0459] line R1line R1

[0460] T1-383 2-Ph, 3-F, 4-CECH T1-432 2-CH3, 3-cyclopropyl, 4-Ph T1-384 2-Ph, 3-F, 4-CH3T1-433 2-CH3, 3-CECH, 4-F

[0461] T1-385 2-Ph, 3-CI, 4-F T1-434 2-CH3, 3-CECH, 4-CI T1-386 2-Ph, 3-CI, 4-CI T1-435 2-CH3, 3-CECH, 4-Br T1-387 2-Ph, 3-CI, 4-Br T1-436 2-CH3, 3-CECH, 4-cyclopropyl T1-388 2-Ph, 3-CI, 4-cyclopropyl T1-437 2-CH3, 3-CECH, 4-Ph T1-389 2-Ph, 3-CI, 4-CECH T1-438 2-CH3, 3-Ph, 4-F

[0462] T1-390 2-Ph, 3-CI, 4-CH3 T1-439 2-CH3, 3-Ph, 4-CI

[0463] T1-391 2-Ph, 3-Br, 4-F T1-440 2-CH3, 3-Ph, 4-Br

[0464] T1-392 2-Ph, 3-Br, 4-CI T1-441 2-CH3, 3-Ph, 4-cyclopropyl T1-393 2-Ph, 3-Br, 4-cyclopropyl T1-442 2-CH3, 3-Ph, 4-CECH T1-394 2-Ph, 3-Br, 4-CECH T1-443 2-F, 3-F, 5-F

[0465] T1-395 2-Ph, 3-Br, 4-CH3 T1-444 2-F, 3-F, 5-CI

[0466] T1-396 2-Ph, 3-cyclopropyl, 4-F T1-445 2-F, 3-CI, 5-F

[0467] T1-397 2-Ph, 3-cyclopropyl, 4-CI T1-446 2-F, 3-CI, 5-CI

[0468] T1-398 2-Ph, 3-cyclopropyl, 4-Br T1-447 2-F, 3-Br, 5-F

[0469] T1-399 2-Ph, 3-cyclopropyl, 4-CECH T1-448 2-F, 3-Br, 5-CI

[0470] T1-400 2-Ph, 3-cyclopropyl, 4-CH3 T1-449 2-F, 3-cyclopropyl, 5-F T1-401 2-Ph, 3-CECH, 4-F T1-450 2-F, 3-cyclopropyl, 5-CI T1-402 2-Ph, 3-CECH, 4-CI T1-451 2-F, 3-CECH, 5-F

[0471] T1-403 2-Ph, 3-CECH, 4-Br T1-452 2-F, 3-CECH, 5-CI

[0472] T1-404 2-Ph, 3-CECH, 4-cyclopropyl T1-453 2-F, 3-Ph, 5-F

[0473] T1-405 2-Ph, 3-CECH, 4-CH3 T1-454 2-F, 3-Ph, 5-CI

[0474] T1-406 2-Ph, 3-CH3, 4-F T1-455 2-F, 3-CH3, 5-F

[0475] T1-407 2-Ph, 3-CH3, 4-CI T1-456 2-F, 3-CH3, 5-CI

[0476] T1-408 2-Ph, 3-CH3, 4-Br T1-457 2-CI, 3-F, 5-F

[0477] T1-409 2-Ph, 3-CH3, 4-cyclopropyl T1-458 2-CI, 3-F, 5-CI

[0478] T1-410 2-Ph, 3-CH3, 4-CECH T1-459 2-CI, 3-CI, 5-F

[0479] T1-411 2-CH3, 3-F, 4-F T1-460 2-CI, 3-CI, 5-CI

[0480] T1-412 2-CH3, 3-F, 4-CI T1-461 2-CI, 3-Br, 5-F

[0481] T1-413 2-CH3, 3-F, 4-Br T1-462 2-CI, 3-Br, 5-CI

[0482] T1-414 2-CH3, 3-F, 4-cyclopropyl T1-463 2-CI, 3-cyclopropyl, 5-F T1-415 2-CH3, 3-F, 4-CECH T1-464 2-CI, 3-cyclopropyl, 5-CI T1-416 2-CH3, 3-F, 4-Ph T1-465 2-CI, 3-CECH, 5-F

[0483] T1-417 2-CH3, 3-CI, 4-F T1-466 2-CI, 3-CECH, 5-CI

[0484] T1-418 2-CH3, 3-CI, 4-CI T1-467 2-CI, 3-Ph, 5-F

[0485] T1-419 2-CH3, 3-CI, 4-Br T1-468 2-CI, 3-Ph, 5-CI

[0486] T1-420 2-CH3, 3-CI, 4-cyclopropyl T1-469 2-CI, 3-CH3, 5-F

[0487] T1-421 2-CH3, 3-CI, 4-CECH T1-470 2-CI, 3-CH3, 5-CI

[0488] T1-422 2-CH3, 3-CI, 4-Ph T1-471 2-Br, 3-F, 5-F

[0489] T1-423 2-CH3, 3-Br, 4-F T1-472 2-Br, 3-F, 5-CI

[0490] T1-424 2-CH3, 3-Br, 4-CI T1-473 2-Br, 3-CI, 5-F

[0491] T1-425 2-CH3, 3-Br, 4-cyclopropyl T1-474 2-Br, 3-CI, 5-CI

[0492] T1-426 2-CH3, 3-Br, 4-CECH T1-475 2-Br, 3-cyclopropyl, 5-F T1-427 2-CH3, 3-Br, 4-Ph T1-476 2-Br, 3-cyclopropyl, 5-CI T1-428 2-CH3, 3-cyclopropyl, 4-F T1-477 2-Br, 3-CECH, 5-F

[0493] T1-429 2-CH3, 3-cyclopropyl, 4-CI T1-478 2-Br, 3-CECH, 5-CI

[0494] T1-430 2-CH3, 3-cyclopropyl, 4-Br T1-479 2-Br, 3-Ph, 5-F

[0495]

[0496] T1-431 2-CH3, 3-cyclopropyl, 4-CECH

[0497]

[0498] T1-480 2-Br, 3-Ph, 5-CI BASF SE 241388

[0499] 28

[0500] line R1line R1

[0501] T1-481 2-Br, 3-CH3, 5-F T1-530 2-CH3, 3-Ph, 5-CI

[0502] T1-482 2-Br, 3-CH3, 5-CI T1-531 2-F, 3-F, 6-F

[0503] T1-483 2-cyclopropyl, 3-F, 5-F T1-532 2-F, 3-F, 6-CI

[0504] T1-484 2-cyclopropyl, 3-F, 5-CI T1-533 2-F, 3-CI, 6-F

[0505] T1-485 2-cyclopropyl, 3-CI, 5-F T1-534 2-F, 3-CI, 6-CI

[0506] T1-486 2-cyclopropyl, 3-CI, 5-CI T1-535 2-F, 3-Br, 6-F

[0507] T1-487 2-cyclopropyl, 3-Br, 5-F T1-536 2-F, 3-Br, 6-CI

[0508] T1-488 2-cyclopropyl, 3-Br, 5-CI T1-537 2-F, 3-cyclopropyl, 6-F T1-489 2-cyclopropyl, 3-CECH, 5-F T1-538 2-F, 3-cyclopropyl, 6-CI T1-490 2-cyclopropyl, 3-CECH, 5-CI T1-539 2-F, 3-CECH, 6-F

[0509] T1-491 2-cyclopropyl, 3-Ph, 5-F T1-540 2-F, 3-CECH, 6-CI

[0510] T1-492 2-cyclopropyl, 3-Ph, 5-CI T1-541 2-F, 3-Ph, 6-F

[0511] T1-493 2-cyclopropyl, 3-CH3, 5-F T1-542 2-F, 3-Ph, 6-CI

[0512] T1-494 2-cyclopropyl, 3-CH3, 5-CI T1-543 2-F, 3-CH3, 6-F

[0513] T1-495 2-CECH, 3-F, 5-F T1-544 2-F, 3-CH3, 6-CI

[0514] T1-496 2-CECH, 3-F, 5-CI T1-545 2-CI, 3-F, 6-F

[0515] T1-497 2-CECH, 3-CI, 5-F T1-546 2-CI, 3-F, 6-CI

[0516] T1-498 2-CECH, 3-CI, 5-CI T1-547 2-CI, 3-CI, 6-F

[0517] T1-499 2-CECH, 3-Br, 5-F T1-548 2-CI, 3-CI, 6-CI

[0518] T1-500 2-CECH, 3-Br, 5-CI T1-549 2-CI, 3-Br, 6-F

[0519] T1-501 2-CECH, 3-cyclopropyl, 5-F T1-550 2-CI, 3-Br, 6-CI

[0520] T1-502 2-CECH, 3-cyclopropyl, 5-CI T1-551 2-CI, 3-cyclopropyl, 6-F T1-503 2-CECH, 3-Ph, 5-F T1-552 2-CI, 3-cyclopropyl, 6-CI T1-504 2-CECH, 3-Ph, 5-CI T1-553 2-CI, 3-CECH, 6-F

[0521] T1-505 2-CECH, 3-CH3, 5-F T1-554 2-CI, 3-CECH, 6-CI T1-506 2-CECH, 3-CH3, 5-CI T1-555 2-CI, 3-Ph, 6-F

[0522] T1-507 2-Ph, 3-F, 5-F T1-556 2-CI, 3-Ph, 6-CI

[0523] T1-508 2-Ph, 3-F, 5-CI T1-557 2-CI, 3-CH3, 6-F

[0524] T1-509 2-Ph, 3-CI, 5-F T1-558 2-CI, 3-CH3, 6-CI

[0525] T1-510 2-Ph, 3-CI, 5-CI T1-559 2-Br, 3-F, 6-F

[0526] T1-511 2-Ph, 3-Br, 5-F T1-560 2-Br, 3-F, 6-CI

[0527] T1-512 2-Ph, 3-Br, 5-CI T1-561 2-Br, 3-CI, 6-F

[0528] T1-513 2-Ph, 3-cyclopropyl, 5-F T1-562 2-Br, 3-CI, 6-CI

[0529] T1-514 2-Ph, 3-cyclopropyl, 5-CI T1-563 2-Br, 3-cyclopropyl, 6-F T1-515 2-Ph, 3-CECH, 5-F T1-564 2-Br, 3-cyclopropyl, 6-CI T1-516 2-Ph, 3-CECH, 5-CI T1-565 2-Br, 3-CECH, 6-F

[0530] T1-517 2-Ph, 3-CH3, 5-F T1-566 2-Br, 3-CECH, 6-CI T1-518 2-Ph, 3-CH3, 5-CI T1-567 2-Br, 3-Ph, 6-F

[0531] T1-519 2-CH3, 3-F, 5-F T1-568 2-Br, 3-Ph, 6-CI

[0532] T1-520 2-CH3, 3-F, 5-CI T1-569 2-Br, 3-CH3, 6-F

[0533] T1-521 2-CH3, 3-CI, 5-F T1-570 2-Br, 3-CH3, 6-CI

[0534] T1-522 2-CH3, 3-CI, 5-CI T1-571 2-cyclopropyl, 3-F, 6-F T1-523 2-CH3, 3-Br, 5-F T1-572 2-cyclopropyl, 3-F, 6-CI T1-524 2-CH3, 3-Br, 5-CI T1-573 2-cyclopropyl, 3-CI, 6-F T1-525 2-CH3, 3-cyclopropyl, 5-F T1-574 2-cyclopropyl, 3-CI, 6-CI T1-526 2-CH3, 3-cyclopropyl, 5-CI T1-575 2-cyclopropyl, 3-Br, 6-F T1-527 2-CH3, 3-CECH, 5-F T1-576 2-cyclopropyl, 3-Br, 6-CI T1-528 2-CH3, 3-CECH, 5-CI T1-577 2-cyclopropyl, 3-CECH, 6-F

[0535]

[0536] T1-529 2-CH3, 3-Ph, 5-F

[0537]

[0538] T1-578 2-cyclopropyl, 3-CECH, 6-CI BASF SE 241388

[0539] 29

[0540] line R1line R1

[0541] T1-579 2-cyclopropyl, 3-Ph, 6-F T1-628 2-F, 4-CECH, 5-CI

[0542] T1-580 2-cyclopropyl, 3-Ph, 6-CI T1-629 2-F, 4-Ph, 5-F

[0543] T1-581 2-cyclopropyl, 3-CH3, 6-F T1-630 2-F, 4-Ph, 5-CI

[0544] T1-582 2-cyclopropyl, 3-CH3, 6-CI T1-631 2-F, 4-CH3, 5-F

[0545] T1-583 2-CECH, 3-F, 6-F T1-632 2-F, 4-CH3, 5-CI

[0546] T1-584 2-CECH, 3-F, 6-CI T1-633 2-CI, 4-F, 5-F

[0547] T1-585 2-CECH, 3-CI, 6-F T1-634 2-CI, 4-F, 5-CI

[0548] T1-586 2-CECH, 3-CI, 6-CI T1-635 2-CI, 4-CI, 5-F

[0549] T1-587 2-CECH, 3-Br, 6-F T1-636 2-CI, 4-CI, 5-CI

[0550] T1-588 2-CECH, 3-Br, 6-CI T1-637 2-CI, 4-Br, 5-F

[0551] T1-589 2-CECH, 3-cyclopropyl, 6-F T1-638 2-CI, 4-Br, 5-CI

[0552] T1-590 2-CECH, 3-cyclopropyl, 6-CI T1-639 2-CI, 4-cyclopropyl, 5-F T1-591 2-CECH, 3-Ph, 6-F T1-640 2-CI, 4-cyclopropyl, 5-CI T1-592 2-CECH, 3-Ph, 6-CI T1-641 2-CI, 4-CECH, 5-F

[0553] T1-593 2-CECH, 3-CH3, 6-F T1-642 2-CI, 4-CECH, 5-CI T1-594 2-CECH, 3-CH3, 6-CI T1-643 2-CI, 4-Ph, 5-F

[0554] T1-595 2-Ph, 3-F, 6-F T1-644 2-CI, 4-Ph, 5-CI

[0555] T1-596 2-Ph, 3-F, 6-CI T1-645 2-CI, 4-CH3, 5-F

[0556] T1-597 2-Ph, 3-CI, 6-F T1-646 2-CI, 4-CH3, 5-CI

[0557] T1-598 2-Ph, 3-CI, 6-CI T1-647 2-Br, 4-F, 5-F

[0558] T1-599 2-Ph, 3-Br, 6-F T1-648 2-Br, 4-F, 5-CI

[0559] T1-600 2-Ph, 3-Br, 6-CI T1-649 2-Br, 4-CI, 5-F

[0560] T1-601 2-Ph, 3-cyclopropyl, 6-F T1-650 2-Br, 4-CI, 5-CI

[0561] T1-602 2-Ph, 3-cyclopropyl, 6-CI T1-651 2-Br, 4-cyclopropyl, 5-F T1-603 2-Ph, 3-CECH, 6-F T1-652 2-Br, 4-cyclopropyl, 5-CI T1-604 2-Ph, 3-CECH, 6-CI T1-653 2-Br, 4-CECH, 5-F

[0562] T1-605 2-Ph, 3-CH3, 6-F T1-654 2-Br, 4-CECH, 5-CI T1-606 2-Ph, 3-CH3, 6-CI T1-655 2-Br, 4-Ph, 5-F

[0563] T1-607 2-CH3, 3-F, 6-F T1-656 2-Br, 4-Ph, 5-CI

[0564] T1-608 2-CH3, 3-F, 6-CI T1-657 2-Br, 4-CH3, 5-F

[0565] T1-609 2-CH3, 3-CI, 6-F T1-658 2-Br, 4-CH3, 5-CI

[0566] T1-610 2-CH3, 3-CI, 6-CI T1-659 2-cyclopropyl, 4-F, 5-F T1-611 2-CH3, 3-Br, 6-F T1-660 2-cyclopropyl, 4-F, 5-CI T1-612 2-CH3, 3-Br, 6-CI T1-661 2-cyclopropyl, 4-CI, 5-F T1-613 2-CH3, 3-cyclopropyl, 6-F T1-662 2-cyclopropyl, 4-CI, 5-CI T1-614 2-CH3, 3-cyclopropyl, 6-CI T1-663 2-cyclopropyl, 4-Br, 5-F T1-615 2-CH3, 3-CECH, 6-F T1-664 2-cyclopropyl, 4-Br, 5-CI T1-616 2-CH3, 3-CECH, 6-CI T1-665 2-cyclopropyl, 4-CECH, 5-F T1-617 2-CH3, 3-Ph, 6-F T1-666 2-cyclopropyl, 4-CECH, 5-CI T1-618 2-CH3, 3-Ph, 6-CI T1-667 2-cyclopropyl, 4-Ph, 5-F T1-619 2-F, 4-F, 5-F T1-668 2-cyclopropyl, 4-Ph, 5-CI T1-620 2-F, 4-F, 5-CI T1-669 2-cyclopropyl, 4-CH3, 5-F T1-621 2-F, 4-CI, 5-F T1-670 2-cyclopropyl, 4-CH3, 5-CI T1-622 2-F, 4-CI, 5-CI T1-671 2-CECH, 4-F, 5-F

[0567] T1-623 2-F, 4-Br, 5-F T1-672 2-CECH, 4-F, 5-CI

[0568] T1-624 2-F, 4-Br, 5-CI T1-673 2-CECH, 4-CI, 5-F

[0569] T1-625 2-F, 4-cyclopropyl, 5-F T1-674 2-CECH, 4-CI, 5-CI T1-626 2-F, 4-cyclopropyl, 5-CI T1-675 2-CECH, 4-Br, 5-F

[0570]

[0571] T1-627 2-F, 4-CECH, 5-F

[0572]

[0573] T1-676 2-CECH, 4-Br, 5-CI BASF SE 241388

[0574] 30

[0575] line R1line R1

[0576] T1-677 2-CECH, 4-cyclopropyl, 5-F T1-726 2-CI, 4-Br, 6-CI

[0577] T1-678 2-CECH, 4-cyclopropyl, 5-CI T1-727 2-CI, 4-cyclopropyl, 6-F T1-679 2-CECH, 4-Ph, 5-F T1-728 2-CI, 4-cyclopropyl, 6-CI T1-680 2-CECH, 4-Ph, 5-CI T1-729 2-CI, 4-CECH, 6-F

[0578] T1-681 2-CECH, 4-CH3, 5-F T1-730 2-CI, 4-CECH, 6-CI T1-682 2-CECH, 4-CH3, 5-CI T1-731 2-CI, 4-Ph, 6-F

[0579] T1-683 2-Ph, 4-F, 5-F T1-732 2-CI, 4-Ph, 6-CI

[0580] T1-684 2-Ph, 4-F, 5-CI T1-733 2-CI, 4-CH3, 6-F

[0581] T1-685 2-Ph, 4-CI, 5-F T1-734 2-CI, 4-CH3, 6-CI

[0582] T1-686 2-Ph, 4-CI, 5-CI T1-735 2-Br, 4-F, 6-F

[0583] T1-687 2-Ph, 4-Br, 5-F T1-736 2-Br, 4-F, 6-CI

[0584] T1-688 2-Ph, 4-Br, 5-CI T1-737 2-Br, 4-CI, 6-F

[0585] T1-689 2-Ph, 4-cyclopropyl, 5-F T1-738 2-Br, 4-CI, 6-CI

[0586] T1-690 2-Ph, 4-cyclopropyl, 5-CI T1-739 2-Br, 4-cyclopropyl, 6-F T1-691 2-Ph, 4-CECH, 5-F T1-740 2-Br, 4-cyclopropyl, 6-CI T1-692 2-Ph, 4-CECH, 5-CI T1-741 2-Br, 4-CECH, 6-F

[0587] T1-693 2-Ph, 4-CH3, 5-F T1-742 2-Br, 4-CECH, 6-CI T1-694 2-Ph, 4-CH3, 5-CI T1-743 2-Br, 4-Ph, 6-F

[0588] T1-695 2-CH3, 4-F, 5-F T1-744 2-Br, 4-Ph, 6-CI

[0589] T1-696 2-CH3, 4-F, 5-CI T1-745 2-Br, 4-CH3, 6-F

[0590] T1-697 2-CH3, 4-CI, 5-F T1-746 2-Br, 4-CH3, 6-CI

[0591] T1-698 2-CH3, 4-CI, 5-CI T1-747 2-cyclopropyl, 4-F, 6-F T1-699 2-CH3, 4-Br, 5-F T1-748 2-cyclopropyl, 4-F, 6-CI T1-700 2-CH3, 4-Br, 5-CI T1-749 2-cyclopropyl, 4-CI, 6-F T1-701 2-CH3, 4-cyclopropyl, 5-F T1-750 2-cyclopropyl, 4-CI, 6-CI T1-702 2-CH3, 4-cyclopropyl, 5-CI T1-751 2-cyclopropyl, 4-Br, 6-F T1-703 2-CH3, 4-CECH, 5-F T1-752 2-cyclopropyl, 4-Br, 6-CI T1-704 2-CH3, 4-CECH, 5-CI T1-753 2-cyclopropyl, 4-CECH, 6-F T1-705 2-CH3, 4-Ph, 5-F T1-754 2-cyclopropyl, 4-CECH, 6-CI T1-706 2-CH3, 4-Ph, 5-CI T1-755 2-cyclopropyl, 4-Ph, 6-F T1-707 2-F, 4-F, 6-F T1-756 2-cyclopropyl, 4-Ph, 6-CI T1-708 2-F, 4-F, 6-CI T1-757 2-cyclopropyl, 4-CH3, 6-F T1-709 2-F, 4-CI, 6-F T1-758 2-cyclopropyl, 4-CH3, 6-CI T1-710 2-F, 4-CI, 6-CI T1-759 2-CECH, 4-F, 6-F

[0592] T1-711 2-F, 4-Br, 6-F T1-760 2-CECH, 4-F, 6-CI

[0593] T1-712 2-F, 4-Br, 6-CI T1-761 2-CECH, 4-CI, 6-F

[0594] T1-713 2-F, 4-cyclopropyl, 6-F T1-762 2-CECH, 4-CI, 6-CI T1-714 2-F, 4-cyclopropyl, 6-CI T1-763 2-CECH, 4-Br, 6-F

[0595] T1-715 2-F, 4-CECH, 6-F T1-764 2-CECH, 4-Br, 6-CI T1-716 2-F, 4-CECH, 6-CI T1-765 2-CECH, 4-cyclopropyl, 6-F T1-717 2-F, 4-Ph, 6-F T1-766 2-CECH, 4-cyclopropyl, 6-CI T1-718 2-F, 4-Ph, 6-CI T1-767 2-CECH, 4-Ph, 6-F

[0596] T1-719 2-F, 4-CH3, 6-F T1-768 2-CECH, 4-Ph, 6-CI T1-720 2-F, 4-CH3, 6-CI T1-769 2-CECH, 4-CH3, 6-F T1-721 2-CI, 4-F, 6-F T1-770 2-CECH, 4-CH3, 6-CI T1-722 2-CI, 4-F, 6-CI T1-771 2-Ph, 4-F, 6-F

[0597] T1-723 2-CI, 4-CI, 6-F T1-772 2-Ph, 4-F, 6-CI

[0598] T1-724 2-CI, 4-CI, 6-CI T1-773 2-Ph, 4-CI, 6-F

[0599]

[0600] T1-725 2-CI, 4-Br, 6-F

[0601]

[0602] T1-774 2-Ph, 4-CI, 6-CI BASF SE 241388

[0603] 31

[0604] line R1line R1

[0605] T1-775 2-Ph, 4-Br, 6-F T1-824 3-Br, 4-F, 5-CI

[0606] T1-776 2-Ph, 4-Br, 6-CI T1-825 3-Br, 4-CI, 5-F

[0607] T1-777 2-Ph, 4-cyclopropyl, 6-F T1-826 3-Br, 4-CI, 5-CI

[0608] T1-778 2-Ph, 4-cyclopropyl, 6-CI T1-827 3-Br, 4-cyclopropyl, 5-F T1-779 2-Ph, 4-C≡CH, 6-F T1-828 3-Br, 4-cyclopropyl, 5-CI T1-780 2-Ph, 4-C≡CH, 6-CI T1-829 3-Br, 4-C≡CH, 5-F

[0609] T1-781 2-Ph, 4-CH3, 6-F T1-830 3-Br, 4-C≡CH, 5-CI T1-782 2-Ph, 4-CH3, 6-CI T1-831 3-Br, 4-Ph, 5-F

[0610] T1-783 2-CH3, 4-F, 6-F T1-832 3-Br, 4-Ph, 5-CI

[0611] T1-784 2-CH3, 4-F, 6-CI T1-833 3-Br, 4-CH3, 5-F

[0612] T1-785 2-CH3, 4-CI, 6-F T1-834 3-Br, 4-CH3, 5-CI

[0613] T1-786 2-CH3, 4-CI, 6-CI T1-835 3-cyclopropyl, 4-F, 5-F T1-787 2-CH3, 4-Br, 6-F T1-836 3-cyclopropyl, 4-F, 5-CI T1-788 2-CH3, 4-Br, 6-CI T1-837 3-cyclopropyl, 4-CI, 5-F T1-789 2-CH3, 4-cyclopropyl, 6-F T1-838 3-cyclopropyl, 4-CI, 5-CI T1-790 2-CH3, 4-cyclopropyl, 6-CI T1-839 3-cyclopropyl, 4-Br, 5-F T1-791 2-CH3, 4-C≡CH, 6-F T1-840 3-cyclopropyl, 4-Br, 5-CI T1-792 2-CH3, 4-C≡CH, 6-CI T1-841 3-cyclopropyl, 4-C≡CH, 5-F T1-793 2-CH3, 4-Ph, 6-F T1-842 3-cyclopropyl, 4-C≡CH, 5-CI T1-794 2-CH3, 4-Ph, 6-CI T1-843 3-cyclopropyl, 4-Ph, 5-F T1-795 3-F, 4-F, 5-F T1-844 3-cyclopropyl, 4-Ph, 5-CI T1-796 3-F, 4-F, 5-CI T1-845 3-cyclopropyl, 4-CH3, 5-F T1-797 3-F, 4-CI, 5-F T1-846 3-cyclopropyl, 4-CH3, 5-CI T1-798 3-F, 4-CI, 5-CI T1-847 3-C≡CH, 4-F, 5-F

[0614] T1-799 3-F, 4-Br, 5-F T1-848 3-C≡CH, 4-F, 5-CI

[0615] T1-800 3-F, 4-Br, 5-CI T1-849 3-C≡CH, 4-CI, 5-F

[0616] T1-801 3-F, 4-cyclopropyl, 5-F T1-850 3-CECH, 4-CI, 5-CI T1-802 3-F, 4-cyclopropyl, 5-CI T1-851 3-CECH, 4-Br, 5-F

[0617] T1-803 3-F, 4-C≡CH, 5-F T1-852 3-C≡CH, 4-Br, 5-CI T1-804 3-F, 4-C≡CH, 5-CI T1-853 3-C≡CH, 4-cyclopropyl, 5-F T1-805 3-F, 4-Ph, 5-F T1-854 3-CECH, 4-cyclopropyl, 5-CI T1-806 3-F, 4-Ph, 5-CI T1-855 3-CECH, 4-Ph, 5-F

[0618] T1-807 3-F, 4-CH3, 5-F T1-856 3-CECH, 4-Ph, 5-CI T1-808 3-F, 4-CH3, 5-CI T1-857 3-CECH, 4-CH3, 5-F T1-809 3-CI, 4-F, 5-F T1-858 3-CECH, 4-CH3, 5-CI T1-810 3-CI, 4-F, 5-CI T1-859 3-Ph, 4-F, 5-F

[0619] T1-811 3-CI, 4-CI, 5-F T1-860 3-Ph, 4-F, 5-CI

[0620] T1-812 3-CI, 4-CI, 5-CI T1-861 3-Ph, 4-CI, 5-F

[0621] T1-813 3-CI, 4-Br, 5-F T1-862 3-Ph, 4-CI, 5-CI

[0622] T1-814 3-CI, 4-Br, 5-CI T1-863 3-Ph, 4-Br, 5-F

[0623] T1-815 3-CI, 4-cyclopropyl, 5-F T1-864 3-Ph, 4-Br, 5-CI

[0624] T1-816 3-CI, 4-cyclopropyl, 5-CI T1-865 3-Ph, 4-cyclopropyl, 5-F T1-817 3-CI, 4-C≡CH, 5-F T1-866 3-Ph, 4-cyclopropyl, 5-CI T1-818 3-CI, 4-C≡CH, 5-CI T1-867 3-Ph, 4-C≡CH, 5-F

[0625] T1-819 3-CI, 4-Ph, 5-F T1-868 3-Ph, 4-C≡CH, 5-CI T1-820 3-CI, 4-Ph, 5-CI T1-869 3-Ph, 4-CH3, 5-F

[0626] T1-821 3-CI, 4-CH3, 5-F T1-870 3-Ph, 4-CH3, 5-CI

[0627] T1-822 3-CI, 4-CH3, 5-CI T1-871 3-CH3, 4-F, 5-F

[0628]

[0629] T1-823 3-Br, 4-F, 5-F

[0630]

[0631] T1-872 3-CH3, 4-F, 5-CI BASF SE 241388

[0632] 32

[0633] line R1line R1

[0634] T1-873 3-CH3, 4-CI, 5-F T1-891 2-F, 3-OCF2Br

[0635] T1-874 3-CH3, 4-CI, 5-CI T1-892 2-F, 3-OCF2Cl

[0636] T1-875 3-CH3, 4-Br, 5-F T1-893 2-CI, 3-OCF2Br

[0637] T1-876 3-CH3, 4-Br, 5-CI T1-894 2-CI, 3-OCF2Cl

[0638] T1-877 3-CH3, 4-cyclopropyl, 5-F T1-895 2-CI, 4-OCF3

[0639] T1-878 3-CH3, 4-cyclopropyl, 5-CI T1-896 2-F, 4-OCF3

[0640] T1-879 3-CH3, 4-C≡CH, 5-F T1-897 2-CH3, 4-CH3

[0641] T1-880 3-CH3, 4-C≡CH, 5-CI T1-898 2-F, 3-OC2H5

[0642] T1-881 3-CH3, 4-Ph, 5-F T1-899 2-F, 3-OPh

[0643] T1-882 3-CH3, 4-Ph, 5-CI T1-900 2-F, 3-O(3-OCH3-Ph)

[0644] T1-883 2-OCF3, 3-CI T1-901 2-F, 3-(1 -piperidyl)

[0645] T1-884 2-CI, 3-OCF3 T1-902 2-F, 3-C(CH3)3

[0646] T1-885 2-F, 3-O-cyclopropyl T1-903 2-F, 3-OC(CH3)3

[0647] T1-886 2-F, 3-OC(O)CH3T1-904 2-F, 3-O(3-OH-Ph)

[0648] T1-887 2-F, 3-CH2OCH3 T1-905 2-F, 3-O(3-OC2H5-Ph)

[0649] T1-888 2-F, 3-CN T1-906 2-F, 3-OCH2-cyclopropyl T1-889 2-F, 3-OCHF2 T1-907 3-SCF3

[0650] T1-890 2-F, 3-CH2CN T1-908 4-SCF3

[0651] T1-891 2-F, 3-CHF2 T1-909 2-F, 3-(4-F-2-pyridyl)

[0652] T1-892 2-F, 3-OCH(CH3)2T1-910 2-F, 3-(6-F-2-pyridyl)

[0653] T1-893 2-F, 3-C(CH3)F2T1-911 2-F, 3-CH2-(CF2)-O-4

[0654] T1-894 2-F, 3-(2-fluorocyclopropyl) T1-912 2-F, 3-O-(CF2)-CH2-4

[0655] T1-895 2-F, 3-(morpholin-4-yl) T1-913 2-CI, 3-CH2-(CF2)-O-4

[0656] T1-896 2-F, 3-S(O)2CI T1-914 2-CI, 3-O-(CF2)-CH2-4

[0657] T1-897 2-CI, 3-OCH3 T1-915 2-F, 3-O-(CF2)-O-4

[0658] T1-898 2-F, 3-OS(O)2CH3T1-916 2-CI, 3-O-(CF2)-O-4

[0659] T1-899 2-CI, 3-OCHF2 T1-917 2-F, 3-O-(CH2)-O-4

[0660]

[0661] T1-890 2-Br, 3-OCHF2

[0662]

[0663] T1-918 2-CI, 3-O-(CH2)-O-4

[0664] Particular preference is further given to compounds I, l-A, l-R-A and l-S-A having R2as defined in Table T2.

[0665] Table T2

[0666] line R2line R2

[0667] T2-1 - T2-12 2-F, 3-Br

[0668] T2-2 2-F T2-13 2-F, 3-CH3

[0669] T2-3 2-CI T2-14 2-CI, 3-F

[0670] T2-4 2-Br T2-15 2-CI, 3-CI

[0671] T2-5 2-CH3 T2-16 2-CI, 3-Br

[0672] T2-6 3-F T2-17 2-CI, 3-CH3

[0673] T2-7 3-CI T2-18 2-Br, 3-F

[0674] T2-8 3-Br T2-19 2-Br, 3-CI

[0675] T2-9 3-CH3 T2-20 2-Br, 3-CH3

[0676] T2-10 2-F, 3-F T2-21 2-CH3, 3-F

[0677]

[0678] T2-11 2-F, 3-CI

[0679]

[0680] T2-22 2-CH3, 3-CI BASF SE 241388

[0681] 33

[0682] line R2line R2

[0683] T2-23 2-CH3, 3-Br T2-72 2-CI, 3-CI, 5-CI T2-24 2-F, 5-F T2-73 2-CI, 3-CI, 5-Br T2-25 2-F, 5-CI T2-74 2-CI, 3-CI, 5-CH3 T2-26 2-F, 5-Br T2-75 2-CI, 3-Br, 5-F T2-27 2-F, 5-CH3 T2-76 2-CI, 3-Br, 5-CI T2-28 2-CI, 5-F T2-77 2-CI, 3-Br, 5-CH3 T2-29 2-CI, 5-CI T2-78 2-CI, 3-CH3, 5-F T2-30 2-CI, 5-Br T2-79 2-CI, 3-CH3, 5-CI T2-31 2-CI, 5-CH3 T2-80 2-CI, 3-CH3, 5-Br T2-32 2-Br, 5-F T2-81 2-Br, 3-F, 5-F T2-33 2-Br, 5-CI T2-82 2-Br, 3-F, 5-CI T2-34 2-Br, 5-CH3 T2-83 2-Br, 3-F, 5-CH3 T2-35 2-CH3, 5-F T2-84 2-Br, 3-CI, 5-F T2-36 2-CH3, 5-CI T2-85 2-Br, 3-CI, 5-CI T2-37 2-CH3, 5-Br T2-86 2-Br, 3-CI, 5-CH3 T2-38 2-F, 6-F T2-87 2-Br, 3-CH3, 5-F T2-39 2-F, 6-CI T2-88 2-Br, 3-CH3, 5-CI T2-40 2-CI, 6-CI T2-89 2-CH3, 3-F, 5-F T2-41 2-Br, 6-F T2-90 2-CH3, 3-F, 5-CI T2-42 2-Br, 6-CI T2-91 2-CH3, 3-F, 5-Br T2-43 2-CH3, 6-F T2-92 2-CH3, 3-CI, 5-F T2-44 2-CH3, 6-CI T2-93 2-CH3, 3-CI, 5-CI T2-45 3-F, 5-F T2-94 2-CH3, 3-CI, 5-Br T2-46 3-F, 5-CI T2-95 2-CH3, 3-Br, 5-F T2-47 3-F, 5-Br T2-96 2-CH3, 3-Br, 5-CI T2-48 3-F, 5-CH3 T2-97 2-F, 3-F, 6-F T2-49 3-CI, 5-CI T2-98 2-F, 3-F, 6-CI T2-50 3-CI, 5-Br T2-99 2-F, 3-CI, 6-F T2-51 3-CI, 5-CH3 T2-100 2-F, 3-CI, 6-CI T2-52 3-Br, 5-CH3 T2-101 2-F, 3-Br, 6-F T2-53 2-F, 3-F, 5-F T2-102 2-F, 3-Br, 6-CI T2-54 2-F, 3-F, 5-CI T2-103 2-F, 3-CH3, 6-F T2-55 2-F, 3-F, 5-Br T2-104 2-F, 3-CH3, 6-CI T2-56 2-F, 3-F, 5-CH3 T2-105 2-CI, 3-F, 6-F T2-57 2-F, 3-CI, 5-F T2-106 2-CI, 3-F, 6-CI T2-58 2-F, 3-CI, 5-CI T2-107 2-CI, 3-CI, 6-F T2-59 2-F, 3-CI, 5-Br T2-108 2-CI, 3-CI, 6-CI T2-60 2-F, 3-CI, 5-CH3 T2-109 2-CI, 3-Br, 6-F T2-61 2-F, 3-Br, 5-F T2-110 2-CI, 3-Br, 6-CI T2-62 2-F, 3-Br, 5-CI T2-111 2-CI, 3-CH3, 6-F T2-63 2-F, 3-Br, 5-CH3 T2-112 2-CI, 3-CH3, 6-CI T2-64 2-F, 3-CH3, 5-F T2-113 2-Br, 3-F, 6-F T2-65 2-F, 3-CH3, 5-CI T2-114 2-Br, 3-F, 6-CI T2-66 2-F, 3-CH3, 5-Br T2-115 2-Br, 3-CI, 6-F T2-67 2-CI, 3-F, 5-F T2-116 2-Br, 3-CI, 6-CI T2-68 2-CI, 3-F, 5-CI T2-117 2-Br, 3-CH3, 6-F T2-69 2-CI, 3-F, 5-Br T2-118 2-Br, 3-CH3, 6-CI T2-70 2-CI, 3-F, 5-CH3 T2-119 2-CH3, 3-F, 6-F

[0684]

[0685] T2-71 2-CI, 3-CI, 5-F

[0686]

[0687] T2-120 2-CH3, 3-F, 6-CI BASF SE 241388

[0688] 34

[0689] line R2line R2

[0690] T2-121 2-CH3, 3-CI, 6-F

[0691]

[0692] T2-124 2-CH3, 3-Br, 6-CI

[0693] T2-122 2-CH3, 3-CI, 6-CI

[0694]

[0695] T2-123 2-CH3, 3-Br, 6-F

[0696] Particular preference is also given to compounds I, l-A, l-R-A and l-S-A having substituent R3as defined in Table T3.

[0697] Table T3.

[0698] line R3line R3

[0699] T3-1 F T3-4 CN

[0700] T3-2 Cl T3-5 CH3

[0701]

[0702] T3-3 Br

[0703]

[0704] T3-6 C2H5

[0705] Specifically preferred are individual compounds of formula l-A enumerated as (l-A). T1-1 / T2-1 / T3-1 to (l-A). T1-897 / T2-124 / T3-6, wherein R1in each case corresponds to a respective line of Table T1 (i.e. lines T1-1 to T1-897), R2in each case corresponds to a respective line of Table T2 (i.e. lines T2-1 to T2-124) and R3in each case corresponds to a respective line of Table T3 (T3-1 to T3-6).

[0706] Specifically preferred are also individual compounds of formula l-R-A enumerated as (l-R-A). T1-1 / T2-1 / T3-1 to (l-R-A). T1-897 / T2-124 / T3-6, wherein R1in each case corresponds to a respective line of Table T1 (i.e. lines T1-1 to T1-897), R2in each case corresponds to a respective line of Table T2 (i.e. lines T2-1 to T2-124) and R3in each case corresponds to a respective line of Table T3 (T3-1 to T3-6).

[0707] Specifically preferred are also individual compounds of formula l-S-A enumerated as (l-S-A). T1-1 / T2-1 / T3-1 to (l-S-A). T1-897 / T2-124 / T3-6, wherein R1in each case corresponds to a respective line of Table T1 (i.e. lines T1-1 to T1-897), R2in each case corresponds to a respective line of Table T2 (i.e. lines T2-1 to T2-124) and R3in each case corresponds to a respective line of Table T3 (T3-1 to T3-6).

[0708] The below example is given for a better understanding of how the enumerations are assigned to the individual compounds. Thus, the compound (l-A). T1-454 / T2-71 / T3-2 denotes a compound of formula l-A, wherein

[0709] R1is 2-F, 3-Ph, 5-CI (line T1-454 of Table T1),

[0710] R2is 2-CI, 3-CI, 5-F (line T2-71 of Table T2),

[0711] R3is Cl (line T3-2 of Table T3).

[0712] Compounds I can be prepared according to W02001 / 046152 A1 (p. 5-7). The starting materials are either known or can be prepared by standard laboratory methods. If individual compounds I BASF SE 241388

[0713] 35

[0714] cannot be obtained by the routes described therein, they can be prepared by derivatization of other compounds I by standard laboratory methods.

[0715] To expand the spectrum of activity and prevent herbicidal resistance development the compounds of formula I may be applied in combination with other herbicides. Hence, the present invention also provides compositions comprising a compound of formula I (component A) and a further herbicidal compound (component B).

[0716] Further, it may be useful to apply the compounds I in combination with safeners (C). Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the compounds 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 post-emergence application of the useful plant. Hence, the present invention additionally provides compositions comprising a compound of formula I (component A) and a safener (component C).

[0717] The present invention additionally provides compositions comprising a compound I (component A), a further herbicide (component B) and a safener (component C).

[0718] The present invention additionally provides compositions comprising a compound of formula (I) (component A); optionally a further herbicide (component B) and a safener (component C); and an auxiliary which is customary for formulating crop protection compounds.

[0719] In one embodiment the present invention relates to an agrochemical composition comprising a herbicidally active amount of a compound of formula I and at least 1 inert liquid or solid carrier and, if appropriate, at least 1 surface-active substance.

[0720] In one embodiment the present invention relates to the agrochemical composition comprising a herbicidally active amount of a compound of formula I, a further herbicide and at least 1 inert liquid or solid carrier and, if appropriate, at least 1 surface-active substance.

[0721] Compounds I and compositions comprising compounds I can be converted into the customary agrochemical formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the mixtures according to the present invention. The formulations are prepared in a known manner (cf. US 3, 060, 084, EP-A 707445 (for liquid concentrates), Browning: ’’Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48, Perry’s Chemical Engineer’s Handbook, 4th Ed., McGraw-Hill, New York, 1963, S. 8-57 und ff. WO 91 / 13546, US 4, 172, 714, US 4, 144, 050, US 3, 920, 442, US 5, 180, 587, US 5, 232, 701, US 5, 208, 030, GB 2, 095, 558, US 3, 299, 566, Klingman: Weed Control as a Science (J. Wiley & Sons, New York, 1961), Hance et al.: Weed Control Handbook (8th Ed., Blackwell Scientific, Oxford, 1989) and Mollet, H. and Grubemann, A.: Formulation technology (Wiley VCH Verlag, Weinheim, 2001). BASF SE 241388

[0722] 36

[0723] The formulations generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, most preferably between 0.5 and 90%, by weight of active substances, which means of compound of formula I as the only active substance or of compound of formula I together with further active substances. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

[0724] The agrochemical formulations may also comprise auxiliaries which are customary in agrochemical formulations. The auxiliaries used depend on the particular application form.

[0725] Examples for suitable auxiliaries are solvents, solid carriers, dispersants or emulsifiers (such as further solubilizers, protective colloids, surfactants and adhesion agents) organic and inorganic thickeners, bactericides, anti-freezing agents, anti-foaming agents, if appropriate colorants and tackifiers or binders (e.g. for seed treatment formulations).

[0726] 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 and alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. / V-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.

[0727] 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.

[0728] 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 (Int. Ed. or North American Ed.).

[0729] Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and of alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids, of 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. BASF SE 241388

[0730] 37

[0731] Suitable nonionic surfactants are alkoxylates, / V-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 / V-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 homo- or copolymers of vinyl pyrrolidone, vinyl alcohols or vinyl acetate.

[0732] Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with 1 or 2 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 polyvinyl amines or polyethylene amines.

[0733] Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils and other auxiliaries, e.g. as listed by Knowles, Adjuvants and Additives, Agrow Reports DS256, T& F Informa UK, 2006, chapter 5. Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazoli-nones. 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 hexaCNferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants). Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes and cellulose ethers.

[0734] The agrochemical compositions generally comprise between 5 and 99.9%, preferably between 10 and 99.9%, more preferably between 30 and 99% and in particular between 40 and 90%, by weight of at least 1 auxiliary.

[0735] Various types of oils, wetters, adjuvants, fertilizers or micronutrients and further pesticides (e.g. fungicides, growth regulators, herbicides, insecticides, safeners) may be added to the compositions described herein as premix or, not until immediately prior to use (tank mix). These agents BASF SE 241388

[0736] 38

[0737] can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100: 1, preferably 1: 10 to 10: 1.

[0738] Examples of formulation types are suspensions (SC, OD, FS), emulsifiable concentrates (EC), emulsions (EW, EO, ES), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG), which can be water-soluble or wettable, as well as gel formulations for the treatment of plant propagation materials such as seeds (GF), herein further be-low exemplified in detail:

[0739] 1. Composition types for dilution with water

[0740] i) Water-soluble concentrates (SL, LS)

[0741] 10 parts by weight of compound I or composition comprising compound I are dissolved in 90 parts by weight of water or in a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. The active substance dissolves upon dilution with water. In this way, a formulation having a content of 10% by weight of active substance is obtained.

[0742] ii) Dispersible concentrates (DC)

[0743] 20 parts by weight of compound I or composition comprising compound I are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, e. g. polyvinylpyrrolidone. Dilution with water gives a dispersion. The active substance content is 20% by weight.

[0744] iii) Emulsifiable concentrates (EC)

[0745] 15 parts by weight of compound I or composition comprising compound I are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The composition has an active substance content of 15% by weight.

[0746] iv) Emulsions (EW, EO, ES)

[0747] 25 parts by weight of compound I or composition comprising compound I are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifying machine (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The composition has an active substance content of 25% by weight.

[0748] v) Suspensions (SC, OD, FS)

[0749] In an agitated ball mill, 20 parts by weight of compound I or composition comprising compound I are comminuted with addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. The active substance content in the composition is 20% by weight. BASF SE 241388

[0750] 39

[0751] vi) Water-dispersible granules and water-soluble granules (WG, SG)

[0752] 50 parts by weight of compound I or composition comprising compound I are ground finely with addition of 50 parts by weight of dispersants and wetting agents 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. The composition has an active substance content of 50% by weight.

[0753] vii) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)

[0754] 75 parts by weight of compound I or composition comprising compound I are ground in a rotorstator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active substance. The active substance content of the composition is 75% by weight.

[0755] viii) Gel (GF)

[0756] In an agitated ball mill, 20 parts by weight of compound I or composition comprising compound I are comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance, whereby a composition with 20% (w / w) of active substance is obtained.

[0757] 2. Composition types to be applied undiluted

[0758] ix) Dustable powders (DP, DS)

[0759] 5 parts by weight of compound I or composition comprising compound I are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable composition having an active substance content of 5% by weight.

[0760] x) Granules (GR, FG, GG, MG)

[0761] 0.5 parts by weight of compound I or composition comprising compound I is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted having an active substance content of 0.5% by weight.

[0762] xi) ULV solutions (UL)

[0763] 10 parts by weight of compound I or composition comprising compound I as described herein are dissolved in 90 parts by weight of an organic solvent, e. g. xylene. This gives a composition to be applied undiluted having an active substance content of 10% by weight.

[0764] 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. BASF SE 241388

[0765] 40

[0766] For the purposes of treatment of plant propagation materials, particularly seeds, 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. The compositions in question give, after 2-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, soaking, as well as in-furrow application methods. Preferably, compound I or the compositions 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.

[0767] Various types of oils, wetters, adjuvants, fertilizers or micronutrients and further pesticides (e.g. fungicides, growth regulators, herbicides, insecticides, safeners) may be added to the compounds I or the compositions thereof as premix or, not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0768] The user applies the formulations comprising compounds I 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. 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.

[0769] Individual components of the formulation or partially premixed components, e. g. components comprising compounds I (component A) and optionally components B and / or C, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate. It is immaterial whether the compound I (component A) and components B and / or C are formulated separately or jointly.

[0770] The compounds I or compositions comprising compounds I are suitable as herbicides.

[0771] Therefore, the present invention further relates to the use of a compound I or the use of a composition comprising a compound I for controlling undesired vegetation.

[0772] The invention additionally relates to a method for controlling undesired vegetation which comprises allowing a herbicidally effective amount of a compound I or of compositions comprising a compound I to act on plants, their seed and / or their habitat.

[0773] The undesired vegetation can be controlled in a non-crop area or in the cultivation area of a crop, where weeds grow or may grow. BASF SE 241388

[0774] 41

[0775] 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.

[0776] The term "non-crop area" as used herein refers to any area of land that is not used for the cultivation of crops or agricultural production. For example, the compounds I or compositions comprising compounds I can be used to control weeds and undesired plant growth in turf, lawns, parks and gardens. They can also be used to maintain vegetation-free areas around roads, railways, sidewalks and other infrastructure.

[0777] The term "crop cultivation area" as used herein, refers to any land that is used for growing crops, such as fields, gardens orchards, vineyards, etc. Commonly, herbicides are applied to these areas to control the growth of undesired plants or weeds that can compete with crops for nutrients, water and sunlight.

[0778] As used herein, the term "an effective amount" refers to the quantity or application rate of the herbicidally active compound(s) that is necessary to achieve the desired effect or result. Hence, this is the amount of the herbicidally active compound(s) that is sufficient to effectively control or eliminate the target weeds or plants, while minimizing any adverse effects on non-target organisms or the environment. The specific effective amount may vary depending on factors such as target plant species, application method, environmental conditions and the desired level of control.

[0779] The required application rate of the compounds I or compositions comprising compounds I depends on the density of the undesired vegetation, on the development stage of the plants, on the climatic conditions of the location where the compounds I are used and on the application method. In general, the application rate of compounds I is from 0.1 to 1000 g / ha, preferably from 1 to 500 g / ha, more preferably from 1 to 250 g / ha, even more preferably from 2 to 100 g / ha of active substance.

[0780] The compounds I or compositions comprising compounds I can generally be applied for preplant burn-down, as pre- or post-emergence treatment of the crop or together with the seed of a crop plant, preferably as pre-emergence treatment.

[0781] As used herein, “pre-plant burndown” refers to the practice of applying a herbicide to a field or area before planting crops. The purpose of pre-plant burndown is to control or eliminate existing weeds or vegetation to create a weed-free environment for the crops. Pre-plant burndown can also help to prevent the development of herbicide-resistant weeds, as it reduces the overall weed seed bank in the soil.

[0782] As used herein, “pre-emergence” refers to an herbicide treatment that is applied to an area before the crop has emerged from the ground or growing medium. BASF SE 241388

[0783] 42

[0784] As used herein, “post-emergence” refers to an herbicide treatment that is applied to an area after the crop has germinated and emerged from the ground or growing medium.

[0785] The compounds I or compositions comprising compounds I can be applied in conventional manner by using techniques with which a skilled person is familiar. Suitable techniques include spraying, atomizing, dusting, spreading or watering. The type of application depends on the intended purpose in a well-known manner; in any case, it should ensure the finest possible distribution of the active ingredients.

[0786] Preferably, the compounds I or compositions comprising compounds I are applied to an area by spraying, in particular foliar spraying of an aqueous dilution of the active ingredient of the composition. Application can be carried out by customary spraying techniques using, for example, water as carrier and spray liquor rates of from about 10 to 2000 l / ha or 50 to 1000 l / ha, for example from 100 to 500 l / ha. Application by the low-volume and the ultra-low-volume method is possible, as is application in the form of microgranules.

[0787] If the compounds I or compositions comprising compounds I are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal composition is sprayed, with the aid of the spray apparatus, in such a way that they come into as little contact, if any, as possible with the leaves of the sensitive crop plants while reaching the leaves of undesirable plants which grow underneath or the bare soil (post-directed, lay-by).

[0788] The compounds I or compositions comprising compounds I can be also 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).

[0789] 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.

[0790] The compounds I or compositions comprising compounds I may also be applied in combination with or by utilizing smart agricultural technologies, such as precision agriculture, remote and proximate imaging and image recognition or smart agricultural site management programs. These smart agricultural technologies typically include models, e.g. computer programs, that support the user by considering information from a wide variety of sources to increase the quality and yield of harvested material, reduce damage by pests including the prediction of pest pressure and smart application of crop protection products, secure environmental protection, support quick and reliable agronomic decision making, reduce usage of fertilizers and crop protection products, reduce product residues in consumables increase spatial and temporal precision of agronomical measures, automate processes and enable traceability of measures. BASF SE 241388

[0791] 43

[0792] Commercially available systems which include agronomic models are e.g. FieldScripts™ from The Climate Corporation, Xarvio™ from BASF, AGLogic™ from John Deere, etc.

[0793] Information input for these models include but is not limited to soil data (e.g. pH organic matter content, moisture level, nutrient content such as nitrogen, potassium, phosphorous and micronutrient content); information on the plants that are currently growing or that may grow at the area of interest including crop plants and / or weeds (e.g. type of plant, chlorophyl levels, biomass, growth stage, plant health, plant water status, plant growth models, genetic traits, biotic damage by infestation or infection with pests, abiotic damage as caused by drought or nutrient stress etc.); weather information (e.g. information on past and present and forecast of future temperature, humidity and / or precipitation); information on the location of the area and directly derivable information thereof (e.g. terrain features like altitude, slope, water bodies, sun exposure and hours of sunshine per day, vegetation period, etc.); information on pest pressure (e.g. information of the past or present occurrence of unwanted vegetation, fungal diseases and invertebrate pests at the area of interest, at neighboring areas, the region or the vegetation zone); information on beneficial organisms (e.g. information of the past or present occurrence of beneficial organisms at the area of interest, at neighboring areas, the region or the vegetation zone); and / or historic information of any of the aforementioned (e.g. information on previous seasons or of an earlier point in time of the same season).

[0794] The information usable for precision agriculture may be based on input by at least 1 user, be accessible from external data sources and databases or be based on sensor data. Data sources typically include proximate-detection systems like soil-borne sensors and remote sensing as may be achieved by imaging with unmanned airborne vehicles like drones or satellites. Imaging technologies includes poly- and multispectral imagery in the UV-VIS, NIR and UV spectrum. Sensors may be included in an Internet-of-Things system and may be directly or indirectly connected to the processing unit, e.g. via a wireless network and / or cloud applications. The information is typically taken into account by at least 1 processing unit and used to provide recommendations, generate control signals (e.g. for the control of agricultural machinery like tractors, drones, irrigation systems, farm management systems and the like) and / or generate (digital) maps on the area of interest. These (digital) maps contain spatially and optionally temporally resolved information of the agricultural site, wherein the information may contain information directly gathered as described above, combinations thereof or derived thereof, such as pest pressure, nutrient levels and the like. The recommendations, control signals and (digital) maps may relate to or be used for controlling the application of water, nutrients, agrochemical products or plant propagation material to the field of interest or for taking other management measures like tilling, physical or laser-induced weeding.

[0795] Typical technologies that are used in smart agricultural technologies include self-steering robots (such as tractors, harvesters, drones), artificial intelligence (e.g. machine learning), imaging technologies (e.g. image segmentation technologies), big data analysis and model generation, cloud computing and machine-to-machine communication. BASF SE 241388

[0796] 44

[0797] Precision agriculture such as precision farming is characterized by spatially and / or temporally resolved, targeted application of active ingredients like pesticides, preferably the compositions according to the present invention, plant-growth-regulators, fertilizers and / or water including the variation of application rates over the agronomic site, zone or spot application and of the spatially and / or temporally resolved, targeted planting or seeding of desired plant propagation material to a agronomic site. Precision farming typically includes the use of geo-positioning technologies like GPS for gaining information on the location and boundaries of the area of interest, the utilized application equipment, sensing equipment and recorded data and to control the actions of farm vehicles such as spraying. By combining geo-positioning data with (digital) maps, it is possible to (semi)-automate agricultural measures at the site of interest, e.g. by using (semi)-autonomous spraying or seeding equipment.

[0798] Precision farming may typically include the application of smart spraying equipment, e.g. spot spraying and precision spraying at a farm, e.g. by irrigation systems, tractors, robots, helicopters, airplanes, unmanned aerial vehicles, such as drones. Such equipment usually includes input sensors (such as a camera) and a processing unit configured to analyze the input data and configured to provide a recommendation or decision based on the analysis of the input data to apply the compositions of the invention to the agronomic site, e.g. the soil or to control pests in a specific and precise manner.

[0799] For example, weeds may be detected, identified and / or classified from imagery acquired by a camera. Such identification and / or classification can make use of image processing algorithms, which may utilize artificial intelligence (e.g. machine learning algorithms) or decision trees. In this manner, the combinations or compositions described herein can be applied at the required location, point in time and dose rate.

[0800] The compounds I and compositions comprising compounds I have an outstanding herbicidal activity against undesired vegetation, i.e. against a broad spectrum of economically important harmful monocotyledonous and dicotyledonous weeds.

[0801] According to one embodiment, the compounds I or compositions comprising compounds I are used to control monocotyledonous weeds, such as weeds from the genera Aegilops spp., Ag-ropyron spp., Agrostis spp., Alisma spp., Alopecurus spp., Aneilema spp., Apera spp., Asphodel us spp., Avena spp., Axonopus spp., Bolboschoenus spp., Brachia ria spp., Bromus spp., Cenchrus spp., Chloris spp., Commelina spp., Cynodon spp., Cyperus spp., Dactyloctenium spp., Digitaria spp., Echinochloa spp., Echinodorus spp., Eichhornia spp., Eleocharis spp., Eleusine spp., Elymus spp., Eragrostis spp., Eriochloa spp., Fimbristylis spp., Heteranthera spp., Hordeum spp., Hydrilla spp., Imperata spp., Ischaemum spp., Kyllinga spp., Leersia spp., Lepto-chloa spp., Limnobium spp., Limnocharis spp., Lolium spp., Luziola spp., Melinis spp., Mono-choria spp., Murdannia spp., Najas spp., Oryza spp., Ottochloa spp., Panicum spp., Paspalum spp., Pennisetum spp., Phalaris spp., Phleum spp., Phragmites spp., Pistia spp., Poa spp., BASF SE 241388

[0802] 45

[0803] Puccinellia spp., Rottboellia spp., Sagittaria spp., Scirpus spp., Sclerochloa spp., Schoeno-plectiella spp., Secale spp., Setaria spp., Sorghum spp., Spirodela spp., Urochloa spp., Zea spp..

[0804] Preferred examples of monocotyledonous weeds controlled by the compounds I or compositions comprising compounds I are selected from Aegilops cylindrica, Agropyron repens, Alisma canaliculatum, Alisma plantago-aquatica, Alisma lanceolatum, Alopecurus myosuroides, Apera spica-venti, Avena fatua, Avena sativa, Avena sterilis, Axonopus affinis, Bolboschoenus fluviati-lis, Bolboschoenus koshevnikovii, Brachiaria decumbens, Brachia ria plantaginea, Brachiaria platyphylla, Bromus arvensis, Bromus diandrus, Bromus commutatus, Bromus inermis, Bromus japonicus, Bromus mollis, Bromus rigidus, Bromus rubens L., Bromus scoparius, Bromus secal-inus L., Bromus sterilis, Bromus tectorum, Cenchrus echinatus, Chloris virgata, Commelina ben-ghalensis, Commelina communis, Commelina diffusa, Commelina erecta, Commelina latifolia, Commelina virginica, Cynodon dactylon, Cyperus compressus, Cyperus difformis, Cyperus es-culentus, Cyperus flaccidus, Cyperus globosus, Cyperus ferax, Cyperus iria, Cyperus kylingia, Cyperus malaccensis, Cyperus microiria, Cyperus nipponicus, Cyperus odoratus, Cyperus ro-tundus, Cyperus serotinus, Dactyloctenium aegyptium, Digitaria horizontalis, Digitaria insularis, Digitaria ischaemum, Digitaria sanguinalis, Eleocharis acicularis, Eleocharis kuroguwai, Eleusine indica, Elymus repens, Eragrostis pectinacea, Eriochloa acuminata, Eriochloa gracilis, Echinochloa coIonum, Echinochloa crus-galli, Eriochloa villosa, Hordeum murinum, Hordeum vulgare, Hydrilla verticillata, Kyllinga brevifolia, Kyllinga gracillima, Leptochloa filiformis, Lepto-chloa fusca, Leptochloa uninervia, Limnobium spongia, Limnocharis flava, Lol i urn multiflorum, Lolium perenne, Lolium rigidum, Melinis repens, Murdannia keisak, Najas guadalupensis, Oryza sativa, Ottochloa nodosa, Panicum capillare, Panicum dichotomiflorum, Panicum maximum, Panicum miliaceum, Pennisetum clandestinum, Pennisetum glaucum, Pistia stratiotes, Poa annua, Poa trivialis L., Sagittaria aginashi, Sagittaria montevidensis, Sagittaria pygmaea, Sagittaria sagittifolia, Sagittaria trifolia, Schoenoplectiella hotarui, Schoenoplectiella juncoides, Schoenoplectiella mucronatus, Schoenoplectiella nipponicus, Schoenoplectiella triangulatus, Schoenoplectiella triqueter, Schoenoplectiella wallichii, Secale cereale, Setaria faberi, Setaria glauca, Setaria italica, Setaria lutescens, Setaria palmifolia, Setaria pumila, Setaria verticillata, Setaria viridis, Sorghum halepense, Sorghum vulgare, Spirodela polyrhiza, Urochloa paricoides, Urochloa or Brachiaria platyphylla, Zea mays

[0805] According to another embodiment, the compounds I or compositions comprising compounds I are used to control dicotyledonous weeds, such as weeds selected from the genera Abutilon spp., Acalypha spp., Acanthospermum spp., Aeschynomene spp., Aethusa spp., Ageratum spp., Alternanthera spp., Amaranthus spp., Ambrosia spp., Ammannia spp., Ammi spp., Amsinckia spp., Anagallis spp., Anchusa spp., Andropogon spp., Anoda spp., Anthemis spp., Aphanes spp., Arabidopsis spp., Arenaria spp., Arctotheca spp., Argemone spp., Artemisia spp., Asclepias spp., Atriplex spp., AzoIla spp., Bacopa spp., Bidens spp., Borreria spp., BASF SE 241388

[0806] 46

[0807] Brassica spp., Buglossoides spp., Calandrinia spp., Callitriche spp., Calystegia spp., Camelina spp., Caperonia spp., Capsella spp., Cardamine spp., Cardiospermum spp., Carduus spp., Cassia spp., Celosia spp., Centaurea spp., Cerastium spp., Ceratophyllum spp., Chenopodium spp., Chrysanthemum spp., Cirsium spp., Cleome spp., Conium spp., Consolida spp., Convolvulus spp., Conyza spp., Coronopus spp., Crassula spp., Crepis spp., Croton spp., Cyclosper-mum spp., Datura spp., Daucus spp., Descurainia spp., Desmodium spp., Draba spp., Echino-cystis spp., Echium spp., Eclipta spp., Elatine spp., Emex spp., Emilia spp., Epilobium spp., Epimedium spp., Equisetum spp., Erechtites spp., Erigeron spp., Erodium spp., Erucastrum spp., Eupatorium spp., Euphorbia spp., Fallopia spp., Fumaria spp., Galeopsis spp., Galinsoga spp., Galium spp., Gamochaeta spp., Geranium spp., Glycine spp., Gnaphalium spp., Gossy-pium spp., Helianthus spp., Heliotropium spp., Hibiscus spp., Hydrocotyle spp., Hyoscyamus spp., Hypochaeris spp., Hyptis spp., Indigofera spp., Ipomoea spp., Jussiaea spp., Iva spp., Kallstroemia spp., Kochia spp., Lactuca spp., Lamium spp., Lapsana spp., Lathyrus spp., Le-onotis spp., Leonurus spp., Lepidium spp., Lindernia spp., Ludwigia spp., Lupinus spp., Lythrum spp., Malva spp., Malvastrum spp., Marchantia spp., Matricaria spp., Medicago spp., Melilotus spp., Mercurialis spp., Mollugo spp., Momordica spp., Myagrum spp., Myosotis spp., Myriophyl-lum spp., Nicandra spp., Oenanthe spp., Oenothera spp., Orobanche spp., Oxalis spp., Papaver spp., Parietaria spp., Parthenium spp., Persica ria spp., Phyllanthus spp., Physalis spp., Pieris spp., Plantago spp., Polygonum spp., Portulaca spp., Potamogeton spp., Pueraria spp., Raphanus spp., Rapistrum spp., Richardia spp., Ricinus spp., Rorippa spp., Rotala spp., Rumex spp., Sagina spp., Salsola spp., Salvinia spp., Senecio spp., Senna spp., Sesbania spp., Sicyos spp., Sida spp., Silene spp., Silybum spp., Sinapis spp., Sisymbrium spp., Solanum spp., Soli-dago spp., Soliva spp., Sonchus spp., Spergula spp., Spermacoce spp., Sphenoclea spp., Sta-chys spp., Stellaria spp., Tagetes spp., Taraxacum spp., Thlaspi spp., Trianthema spp., Tribulus spp., Tridax spp., Trifolium spp., Tripleurospermum spp., Urtica spp., Vaccaria spp., Veronica spp., Vicia spp., Vigna spp., Viola spp., Waltheria spp., Wedelia spp., Xanthium spp., Preferred examples of dicotyledonous weeds controlled by the compounds I or compositions comprising compounds I are selected from

[0808] Abutilon theophrasti, Acalypha australis, Acalypha virginica, Acanthospermum australe, Acan-thospermum hispidum, Aeschynomene indica, Aeschynomene rudis, Aethusa cynapium, Agera-tum conyzoides, Alternanthera philoxeroides, Alternanthera repens, Alternanthera sess / 7 / s, Al-ternanthera tenella, Amaranthus albus, Amaranthus blitoides, Amaranthus blitum, Amaranthus chlorostachys, Amaranthus cruentus, Amaranthus deflexus, Amaranthus hybridus, Amaranthus lividus, Amaranthus palmeri, Amaranthus patulus, Amaranthus powellii, Amaranthus quitensis, Amaranthus retroflexus, Amaranthus rudis, Amaranthus spinosus, Amaranthus tamariscina, Amaranthus tuberculatus, Amaranthus viridis, Ambrosia artemisiifolia, Ambrosia elatior, Ambrosia trifida, Ammannia auriculata, Ammannia coccinea, Ammannia multiflora, Amsinckia intermedia, Amsinckia menziesii, Anagallis arvensis, Anchusa arvensis, Anchusa officinalis, Andropo-gon bicornis, Anoda cristata, Anthemis arvensis, Anthemis cotula, Aphanes arvensis, BASF SE 241388

[0809] 47

[0810] Arabidopsis arenosa, Arabidopsis thaliana, Arctotheca calendula, Argemone mexicana, Artemisia princeps, Artemisia verlotorum, Artemisia vulgaris, Asclepias syriaca, Atriplex patula, AzoIla japonica, AzoIla pinnata, Bidens bipinnata, Bidens frondosa, Bidens pilosa, Bidens subalter-nans, Bidens tripartita, Borreria alata, Brassica juncea, Brassica napus, Brassica nigra, Brassica rapa, Buglossoides arvensis, Calandrinia caulescens, Callitriche palustris, Calystegia hede-racea, Calystegia japonica, Calystegia sepium, Camelina microcarpa, Caperonia palustris, Capsella bursa-pastoris, Cardamine pennsylvanica, Cardiospermum halicacabum, Carduus nutans, Carduus pycnocephalus, Cassia obtusifolia, Cassia occidentalis, Centaurea cyanus, Ce-rastium arvense, Cerastium glomeratum, Cerastium holosteoides, Cerastium vulgatum, Cera-tophyllum demersum, Chenopodium album, Chenopodium ambrosioides, Chenopodium ficifo-lium, Chenopodium hybridum, Chenopodium pratericola, Chrysanthemum segetum, Cirsium arvense, Cirsium vulgare, Cleome affinis, Conium maculatum, Consolida regalis, Convolvulus althaeoides L, Convolvulus arvensis, Convolvulus equitans, Convolvulus japonicus, Convolvulus pellitus, Convolvulus sepium L, Conyza bonariensis, Conyza canadensis, Conyza suma-trensis, Coronopus didymus, Crassula colorata, Crassula sieberiana, Crepis tectorum, Croton capitatus, Croton glandulosus, Croton lobatus, Cyclospermum leptophyllum, Datura stramonium, Daucus carota, Descurainia pinnata, Descurainia sophia, Desmodium adscendens, Des-modium illinoense, Desmodium tortuosum, Draba verna, Echinocystis lobata, Echium plantagi-neum, Eclipta alba, Eclipta prostrata, Elatine californica, Elatine triandra, Emex australis, Emilia sonchifolia, Epilobium adenocaulon, Epilobium angustifolium, Epilobium paniculatum, Equise-tum arvense, Equisetum palustre, Erechtites hieracifolia, Erigeron canadensis, Erigeron stri-gosus, Erodium cicutarium, Erodium moschatum, Erucastrum gallicum, Eupatorium perfoliatum, Euphorbia brasiliensis, Euphorbia cyparissias, Euphorbia esula, Euphorbia helioscopia, Euphorbia heterophylla, Euphorbia hirta, Euphorbia humistrata, Euphorbia maculata, Euphorbia supina, Fallopia convolvulus, Fumaria officinalis, Galeopsis ladanum, Galeopsis tetrahit, Galinsoga cil-iata, Galinsoga parviflora, Galinsoga quadriradiata, Galium aparine, Galium spurium var. Echi-nospermon, Gamochaeta spicata, Geranium carolinense, Geranium carolinianum, Geranium dissectum, Geranium pusilium, Geranium rotundifolium, Glycine max, Gnaphalium obtusifolium, Gnaphalium purpureum, Gnaphalium spicatum, Gossypium hirsutum, Helianthus annuus, Heli- otropium europaeum, Hibiscus trionum, Hydrocotyle ranunculoides, Hydrocotyle sibthorpioides, Hyoscyamus niger, Hypochaeris radicata, Hyptis lophanta, Hyptis suaveolens, Indigofera hirsuta, Indigofera truxillensis, Ipomoea acuminata, Ipomoea aristolochiaefolia, Ipomoea cairica, Ipomoea coccinea, Ipomoea grandifolia, Ipomoea hederacea, Ipomoea hederifolia, Ipomoea lacunosa, Ipomoea nil, Ipomoea purpurea, Ipomoea quamoclit, Ipomoea triloba, Ipomoea wrightii, Iva xanthifolia, Kochia scoparia, Lactuca serriola, Lamium amplexicaule, Lamium purpureum, Lapsana communis, Leonotis nepetaefolia, Leonurus sibiricus, Lepidium virginicum, Ludwigia decurrens, Ludwigia epilobioides, Ludwigia octovalvis, Lupinus angustifolius, Lythrum salicaria, Malva neglecta, Malva parviflora, Malvastrum coromandelianum, Marsilea quadrifolia, Matricaria chamomilla, Matricaria discoidea, Matricaria matricarioides, Matricaria perforata, Medicago polymorpha, Mercurialis annua, Mollugo verticillate, Momordica charantia, Myagrum BASF SE 241388

[0811] 48

[0812] perfoliatum, Myosotis arvensis, Myriophyllum aquaticum, Myriophyllum verticillatum, Oenanthe javanica, Oenothera biennis, Oenothera laciniata, Oxalis corniculata, Oxalis oxyptera, Oxalis stricta, Papaver dubium, Papaver rhoeas, Parthenium hysterophorus, Persicaria lapathi folia, Persicaria maculosa, Phyllanthus corcovadensis, Physalis angulata, Pieris echioides, Plantago asiatica, Plantago lanceolate, Plantago major, Polygonum aviculare, Polygonum convolvulus, Polygonum pensylvanicum, Polygonum persicaria, Portulaca oleracea, Pueraria lobata, Raphanus raphanistrum, Raphanus sativus, Rapistrum rugosum, Richardia brasiliensis, Rich-ardia scabra, Ricinus communis, Rorippa islandica, Rorippa sylvestris, Rotala indica, Rumex acetosella, Rumex crispus, Rumex obtusifolius, Sagina procumbens, Salsola kali, Salsola tragus, Salvinia natans, Senecio brasiliensis, Senecio glabellus, Senecio vulgaris, Senna obtusifo-lia, Sesbania exaltata, Sesbania herbacea, Sicyos angulatus, Side cordifolia, Side glaziovii, Side rhombifolia, Side santaremnensis, Side spinosa, Silene gallica, Silene noctiflora, Silybum marianum, Sinapis arvensis, Sisymbrium altissimum, Sisymbrium irio, Sisymbrium oficinale, So-lanum nigrum, Solanum ptycanthum, Solanum saccharoides, Solanum triflorum, Solidago altis-sima, Soliva sessilis, Sonchus arvensis, Sonchus asper, Sonchus oleraceus, Spergula arvensis, Spermacoce latifolia, Spermacoce verticillate, Stachys arvensis, Stellaria aquatica, Stellaria media, Tagetes minute, Taraxacum officinale, Thlaspi arvense, Tribulus terrestris, Tridax procumbens, Trifolium repens, Tripleurospermum inodorum, Urtica dioica, Urtica urens, Vaccaria pyre midata, Veronica hederifolia, Veronica persica, Vicia angusti folia, Vicia benghalensis L, Vici a cracca, Vicia sativa, Vicia villose, Vigne sinensis, Viola arvensis, Waltheria indica, Wedelia glauca, Xanthium italicum, Xanthium occidentale, Xanthium pensylvanicum, Xanthium stru-marium.

[0813] Especially preferred examples of dicotyledonous weeds on which the compounds I or compositions comprising compounds I act efficiently are selected from the species Amaranthus spp., Erigeron spp., Conyza spp., Kochia spp. and Abutilon spp.

[0814] If not stated otherwise, the compounds I or compositions comprising compounds I are suitable for application in any variety of crops as outlined herein.

[0815] According to the invention all the crop plants (cultivated plants) mentioned herein are understood to comprise all species, subspecies, variants and / or hybrids which belong to the respective cultivated plants, including but not limited to winter and spring varieties, in particular in cereals such as wheat and barley, as well as oilseed rape, e.g. winter wheat, spring wheat, winter barley etc.

[0816] For example, corn is also known as Indian corn or maize (Zea mays) which comprises all kinds of corn such as field corn and sweet corn. According to the invention all maize or corn subspecies and / or varieties are comprised, in particular flour corn (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent corn (Zea mays var. indentata), flint corn (Zea mays var. indurate), sweet corn (Zea mays var. saccharate and var. rugose), waxy corn (Zea mays var. ceratina), BASF SE 241388

[0817] 49

[0818] amylo-maize (high amylose Zea mays varieties), pod corn or wild maize (Zea mays var. tuni-cata) and striped maize (Zea mays var. japonica).

[0819] Further, most soybean cultivars are classifiable into indeterminate and determinate growth habit, whereas Glycine soja, the wild progenitor of soybean, is indeterminate (PNAS 2010, 107 (19) 8563-856). The indeterminate growth habit (Maturity Group, MG 00 to MG 4.9) is characterized by a continuation of vegetative growth after flowering begins whereas determinate soybean varieties (Maturity Group, (MG) 5 to MG 8) characteristically have finished most of their vegetative growth when flowering begins. According to the invention all soybean cultivars or varieties are comprised, in particular indeterminate and determinate cultivars or varieties.

[0820] The compounds I or compositions comprising compounds I are generally suitable for controlling weeds in the following crops (cultivated plants):

[0821] peanuts (groundnuts), soybeans (indeterminate growth habit, determinate growth habit, semideterminate growth habit), lentils, alfalfa (lucerne), limabeans, common bean, tick beans, English peas, corn (field corn, dent corn, flint corn, flour corn, popcorn, waxy corn, sweet corn), wheat (soft wheat, hard wheat, medium wheat, red wheat, white wheat, durum wheat, spelt wheat, club wheat; winter habit and spring habit), rye, triticale, barley (two-row barley, six-row barley, hulless barley, hulless waxy barley; winter habit and spring habit), rice, sorghum, oat, cotton (upland cotton, levant cotton, pima cotton, tree cotton), flax, oilseed rape, canola (winter habit, spring habit), sugarcane, sugar beet, sunflower

[0822] solanaceae vegetables (eggplant, tomato, green pepper, chili pepper, potatos, etc.), sweet pota-tos, cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, crown daisy, artichoke, lettuce, etc.), liliaceae vegetables (welsh onion, onion, garlic, asparagus, etc.), umbelliferae vegetables (carrot, parsley, celery, parsnip, etc.), chenopodiaceae vegetables (spinach, beet, etc.), lami-aceae vegetables (perilla, mint, basil, lavender, etc.), cassava,

[0823] pomaceous fruits (apple, pear, Japanese pear, Chinese quince, quince, etc.), stone fruits (peach, plum, nectarine, Japanese apricot, yellow peach, apricot, prune, cherry (sweet cherry), sour cherry, etc.), citrus fruits (citrus unshiu, orange, lemon, lime, grapefruit, mandarins etc.), nut trees (chestnut, walnut, hazelnut, pecan, almond, pistachio, cashew nut, macadamia nut, etc.), berry fruits (grape, blueberry, cranberry, blackberry, raspberry, strawberry, blackcurrant, redcurrant, etc.), pineapples, persimmon, olive trees, oil palms, castor-oil plants, loquat, coffee (arabica coffee, robusta coffee, liberica coffee), cacao plants, tea plants, banana, tobacco, turf, Bermuda grass (couch grass), hop, natural rubber plants; or ornamental and forestry plants, (e.g. flowers, shrubs, broad-leaved trees, or evergreens (conifer, eucalypt, pine, Norway spruce, etc.)); BASF SE 241388

[0824] 50

[0825] In a preferred embodiment, the compounds I or compositions comprising compounds I are used for controlling weeds in turf and in the following crops: soybeans, cereals (wheat, barley, rye, triti-cale, oat), corn (maize), sorghum, rice, peas, Vicia-beans, Phaseolus-beans, peanuts, cotton, potato, sugarbeet, sugarcane and vegetables.

[0826] In a particularly preferred embodiment, the compounds I or compositions comprising compounds I are used for controlling weeds in in soybeans, cereals (wheat, barley, rye, triticale, oat), and corn (maize).

[0827] In an especially preferred embodiment, the undesirable vegetation is controlled in cereals. In particular, the cereals are selected from the group comprising wheat, barley, rye, oat and triticale.

[0828] The compounds I or compositions comprising compounds I, 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.

[0829] 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.

[0830] 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, 1 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.

[0831] 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. BASF SE 241388

[0832] 51

[0833] 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-hy-droxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.

[0834] 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.

[0835] 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, MZHG0JG, HCEM485, VCO-01981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

[0836] 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.

[0837] Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.

[0838] Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

[0839] 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 cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.1O5, cry1F, cry1Fa2, 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.

[0840] 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. BASF SE 241388

[0841] 52

[0842] Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701, MON87751 and DAS-81419.

[0843] 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 Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.

[0844] Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403 or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.

[0845] Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1, Pj. D6D, Nc. Fad3, fad2-1A and fatb1-A. Soybean events comprising at least 1 of these genes are: 260-05, MON87705 and MON87769.

[0846] 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.

[0847] 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 1 or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbi-cide tolerance and tolerance to abiotic conditions.

[0848] 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 WO2017 / 011288.

[0849] The use of compounds I or compositions comprising compounds I 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 vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.

[0850] 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 BASF SE 241388

[0851] 53

[0852] production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).

[0853] Examples

[0854] A. Synthetic examples

[0855] Synthetic example 1: Preparation of / V-[(1R)-2-[(2,4-difluorobenzoyl)amino]-1-methyl-ethyl]-2-fluoro-3-phenyl-benzamide (Example E1-28)

[0856]

[0857] Step 1:

[0858] Tert-butyl N-[(1R)-2-amino-1-methyl-ethyl]carbamate (300 mg, 1.72 mmol), 2,4-difluorobenzoic acid (272 mg, 1.72 mmol) and N-ethyl-N-isopropyl-propan-2-amine (668 mg, 5.17 mmol) were mixed in THF (25 mL), then 2-chloro-1 -methylpyridinium iodide (439 mg, 1.72 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours. Then the reaction mixture was quenched with water (20 mL), extracted with ethyl acetate (3x15 mL). The organic layer was dried over molecular sieves, filtered and the solvent was evaporated. The crude material was purified by column chromatography to obtain tert-butyl N-[(1R)-2-[(2,4-difluoroben-zoyl)amino]-1-methyl-ethyl]carbamate (441 mg, 1.40 mmol, 81.5% yield) as a white solid.

[0859] Step 2:

[0860] Tert-butyl N-[(1R)-2-[(2,4-difluorobenzoyl)amino]-1-methyl-ethyl]carbamate (430 mg, 1.4 mmol) was dissolved in dichloromethane (80 mL), TFA (1.6 g, 13.7 mmol) was added. The reaction BASF SE 241388

[0861] 54

[0862] mixture was stirred at room temperature for 12 hours. The reactions mixture was then basified to pH 9-10 with aqueous NaOH (2N, 30 mL), extracted with dichloromethane (3x40 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give N-[(2R)-2-aminopropyl]-2,4-difluoro-benzamide (0.27 g, 1.3 mmol, 91.8% yield) as a white solid.

[0863] Step 3:

[0864] N-[(2R)-2-aminopropyl]-2,4-difluoro-benzamide (50 mg, 0.23 mmol), 2-fluoro-3-phenyl-benzoic acid (50 mg, 0.23 mmol) and N-ethyl-N-isopropyl-propan-2-amine (71 mg, 0.7 mmol) were mixed in THF (15 mL), then 2-chloro-1 -methylpyridinium iodide (71 mg, 0.7 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours. Then the reaction mixture was quenched with water (20 mL), extracted with ethyl acetate (3x15 mL). The organic layer was dried over molecular sieves, filtered and the solvent was evaporated. The crude material was purified by column chromatography to obtain N-[(1R)-2-[(2,4-difluorobenzoyl)amino]-1-me-thyl-ethyl]-2-fluoro-3-phenyl-benzamide (example E1-28, 41 mg, 0.096 mmol, 40.5% yield) as a white solid.

[0865] 1H NMR (400 MHz, CDCl3) 68.05 (td, J=8.8, 6.6 Hz, 1H), 8.01 - 7.93 (m, 1H), 7.59 - 7.36 (m, 4H), 7.30 (t, J=7.8 Hz, 1 H), 7.00 - 6.80 (m, 4H), 4.53 - 4.43 (m, 1 H), 3.75 - 3.57 (m, 2H), 1.36 (d, J=6.8 Hz, 3H).

[0866] The compounds of formula l-R-A

[0867]

[0868] depicted in Table E1 were prepared in analogy to Example E1-28.

[0869] Table E1

[0870] ExamLCMS ple No. Compound No R1R2R3

[0871] (M+H) E1-1 (l-R-A). T1-24 / T2-7 / T3-1 2-F, 3-CI 3-CI F 386,9 E1-2 (l-R-A). T1-24 / T2-1 / T3-2 2-F, 3-CI - Cl 368,9 E1-3 (l-R-A). T1-24 / T2-49 / T3-3 2-F, 3-CI 3-CI, 5-CI Br 482,8 E1-4 (l-R-A). T1-24 / T2-49 / T3-1 2-F, 3-CI 3-CI, 5-CI F 422,8 E1-5 (l-R-A). T1-24 / T2-49 / T3-5 2-F, 3-CI 3-CI, 5-CI CH3416,8 E1-6 (l-R-A). T1-26 / T2-1 / T3-1 2-F, 3-cyclopropyl - F 359,1 E1-7 (l-R-A). T1-26 / T2-2 / T3-1 2-F, 3-cyclopropyl 2-F F 377,1

[0872]

[0873] E1-8 (l-R-A). T1-26 / T2-6 / T3-1 2-F, 3-cyclopropyl 3-F F 377,0 BASF SE 241388

[0874] 55

[0875] ExamLCMS ple No. Compound No R1R2R3

[0876] (M+H) E1-9 (l-R-A). T1-26 / T2-7 / T3-2 2-F, 3-cyclopropyl 3-CI Cl 409,0 E1-10 (l-R-A). T1-26 / T2-6 / T3-2 2-F, 3-cyclopropyl 3-F Cl 393,0 E1-11 (l-R-A). T1-26 / T2-6 / T3-4 2-F, 3-cyclopropyl 3-F CN 393,0 E1-12 (l-R-A). T1-26 / T2-7 / T3-4 2-F, 3-cyclopropyl 3-CI CN 400,0 E1-13 (l-R-A). T1-26 / T2-1 / T3-4 2-F, 3-cyclopropyl - CN 366,1 E1-14 (l-R-A). T1-26 / T2-7 / T3-1 2-F, 3-cyclopropyl 3-CI F 393,0 E1-15 (l-R-A). T1-25 / T2-6 / T3-1 2-F, 3-Br 3-F F 414,8 E1-16 (l-R-A). T1-25 / T2-6 / T3-4 2-F, 3-Br 3-F CN 421,9 E1-17 (l-R-A). T1-25 / T2-7 / T3-4 2-F, 3-Br 3-CI CN 439,8 E1-18 (l-R-A). T1-27 / T2-6 / T3-1 2-F, 3-CECH 3-F F 360,9 E1-19 (l-R-A). T1-27 / T2-6 / T3-4 2-F, 3-CECH 3-F CN 367,9 E1-20 (l-R-A). T1-27 / T2-7 / T3-4 2-F, 3-CECH 3-CI CN 383,8 E1-21 (l-R-A). T1-447 / T2-6 / T3-1 2-F, 3-Br, 5-F 3-F F 432,8 E1-22 (l-R-A). T1-28 / T2-6 / T3-1 2-F, 3-Ph 3-F F 413,0 E1-23 (l-R-A). T1-447 / T2-7 / T3-4 2-F, 3-Br, 5-F 3-CI CN 457,8 E1-24 (l-R-A). T1-28 / T2-7 / T3-4 2-F, 3-Ph 3-CI CN 435,9 E1-25 (l-R-A). T1-25 / T2-2 / T3-1 2-F, 3-Br 2-F F 414,9 E1-26 (l-R-A). T1-447 / T2-2 / T3-1 2-F, 3-Br, 5-F 2-F F 434,8 E1-27 (l-R-A). T1-27 / T2-2 / T3-1 2-F, 3-CECH 2-F F 360,9 E1-28 (l-R-A). T1-28 / T2-2 / T3-1 2-F, 3-Ph 2-F F 413,0 E1-29 (l-R-A). T1-25 / T2-1 / T3-1 2-F, 3-Br - F 398,8 E1-30 (l-R-A). T1-447 / T2-1 / T3-1 2-F, 3-Br, 5-F - F 416,8 E1-31 (l-R-A). T1-28 / T2-1 / T3-1 2-F, 3-Ph - F 395,0 E1-32 (l-R-A). T1-25 / T2-7 / T3-1 2-F, 3-Br 3-CI F 430,8 E1-33 (l-R-A). T1-447 / T2-7 / T3-1 2-F, 3-Br, 5-F 3-CI F 450,8 E1-34 (l-R-A). T1-28 / T2-7 / T3-1 2-F, 3-Ph 3-CI F 428,9 E1-35 (l-R-A). T1-27 / T2-1 / T3-1 2-F, 3-CECH - F 343,0 E1-36 (l-R-A). T1-27 / T2-7 / T3-1 2-F, 3-CECH 3-CI F 376,9 E1-37 (l-R-A). T1-28 / T2-6 / T3-4 2-F, 3-Ph 3-F CN 419,9 E1-38 (l-R-A). T1-447 / T2-6 / T3-4 2-F, 3-Br, 5-F 3-F CN 439,8 E1-39 (l-R-A). T1-883 / T2-54 / T3-2 2-OCF3, 3-CI 2-F, 3-F, 5-CI Cl 507,0 E1-40 (l-R-A). T1-884 / T2-54 / T3-2 2-CI, 3-OCF3 2-F, 3-F, 5-CI Cl 505,0 E1-41 (l-R-A). T1-884 / T2-99 / T3-2 2-CI, 3-OCF3 2-F, 3-CI, 6-F Cl 505,0 E1-42 (l-R-A). T1-885 / T2-6 / T3-4 2-F, 3-O-cyclopropyl 3-F CN 400,2 E1-43 (l-R-A). T1-885 / T2-28 / T3-1 2-F, 3-O-cyclopropyl 2-CI, 5-F F 427,2 E1-44 (l-R-A). T1-885 / T2-6 / T3-2 2-F, 3-O-cyclopropyl 3-F Cl 409,2 E1-45 (l-R-A). T1-885 / T2-24 / T3-1 2-F, 3-O-cyclopropyl 2-F, 5-F F 411,2 E1-46 (l-R-A). T1-29 / T2-1 / T3-1 2-F, 3-CH3 F 332,9 E1-47 (l-R-A). T1-24 / T2-1 / T3-1 2-F, 3-CI F 352,9 E1-48 (l-R-A). T1-30 / T2-1 / T3-1 2-CI, 3-F F 352,9 E1-49 (l-R-A). T1-18 / T2-1 / T3-1 4-Br F 380,8 E1-50 (l-R-A). T1-885 / T2-1 / T3-1 2-F, 3-O-cyclopropyl F 375,2

[0877]

[0878] E1-51 (l-R-A). T1-886 / T2-1 / T3-1 2-F, 3-OC(O)CH3F 379,1 BASF SE 241388

[0879] 56

[0880] ExamLCMS ple No. Compound No R1R2R3

[0881] (M+H) E1-52 (l-R-A). T1-887 / T2-1 / T3-1 2-F, 3-CH2OCH3 - F 349,0 E1-53 (l-R-A). T1-888 / T2-1 / T3-1 2-F, 3-CN - F 344,0 E1-54 (l-R-A). T1-30 / T2-25 / T3-1 2-CI, 3-F 2-F, 5-CI F 404,9 E1-55 (l-R-A). T1-30 / T2-6 / T3-1 2-CI, 3-F 3-F F 371,1 E1-56 (l-R-A). T1-30 / T2-7 / T3-1 2-CI, 3-F 3-CI F 386,9 E1-57 (l-R-A). T1-889 / T2-24 / T3-1 2-F, 3-OCHF2 2-F, 5-F F 421,0 E1-58 (l-R-A). T1-889 / T2-1 / T3-1 2-F, 3-OCHF2 - F 385,0 E1-59 (l-R-A). T1-889 / T2-6 / T3-1 2-F, 3-OCHF2 3-F F 403,0 E1-60 (l-R-A). T1-889 / T2-6 / T3-2 2-F, 3-OCHF2 3-F Cl 419,0 E1-61 (l-R-A). T1-889 / T2-3 / T3-1 2-F, 3-OCHF2 2-CI F 419,0 E1-62 (l-R-A). T1-890 / T2-1 / T3-1 2-F, 3-CH2CN F 358,2 E1-63 (l-R-A). T1-891 / T2-1 / T3-1 2-F, 3-CHF2 F 369,0 E1-64 (l-R-A). T1-892 / T2-1 / T3-1 2-F, 3-OCH(CH3)2F 377,2 E1-65 (l-R-A). T1-893 / T2-1 / T3-1 2-F, 3-CCH3F2 F 383,0 E1-66 (l-R-A). T1-894 / T2-1 / T3-1 2-F, 3-(2-F-cyclopropyl) F 377,2 E1-67 (l-R-A). T1-895 / T2-1 / T3-1 2-F, 3-(morpholin-4-yl) F 404,2 E1-68 (l-R-A). T1-896 / T2-1 / T3-1 2-F, 3-S(O)2CI F 417,0 E1-69 (l-R-A). T1-25 / T2-24 / T3-1 2-F, 3-Br 2-F, 5-F F 434,9 E1-70 (l-R-A). T1-29 / T2-24 / T3-1 2-F, 3-CH3 2-F, 5-F F 369,0 E1-71 (l-R-A). T1-24 / T2-24 / T3-1 2-F, 3-CI 2-F, 5-F F 389,0 E1-72 (l-R-A). T1-888 / T2-24 / T3-1 2-F, 3-CN 2-F, 5-F F 380,0 E1-73 (l-R-A). T1-27 / T2-24 / T3-1 2-F, 3-CECH 2-F, 5-F F 379,1 E1-74 (l-R-A). T1-30 / T2-24 / T3-1 2-CI, 3-F 2-F, 5-F F 389,0 E1-75 (l-R-A). T1-26 / T2-24 / T3-1 2-F, 3-cyclopropyl 2-F, 5-F F 395,0 E1-76 (l-R-A). T1-27 / T2-24 / T3-1 2-F, 3-CECH 2-F, 5-F F 397,0 E1-77 (l-R-A). T1-37 / T2-24 / T3-1 2-Br, 3-F 2-F, 5-F F 434,9 E1-78 (l-R-A). T1-31 / T2-24 / T3-1 2-CI, 3-CI 2-F, 5-F F 405,0 E1-79 (l-R-A). T1-23 / T2-24 / T3-1 2-F, 3-F 2-F, 5-F F 373,0 E1-80 (l-R-A). T1-75 / T2-24 / T3-1 2-CI, 4-CI 2-F, 5-F F 404,9 E1-81 (l-R-A). T1-239 / T2-24 / T3-1 2-CI, 3-F, 4-F 2-F, 5-F F 406,9 E1-82 (l-R-A). T1-457 / T2-24 / T3-1 2-CI, 3-F, 5-F 2-F, 5-F F 406,9 E1-83 (l-R-A). T1-43 / T2-24 / T3-1 2-cyclopropyl, 3-F 2-F, 5-F F 395,0 E1-84 (l-R-A). T1-30 / T2-28 / T3-1 2-CI, 3-F 2-CI, 5-F F 404,9 E1-85 (l-R-A). T1-30 / T2-10 / T3-1 2-CI, 3-F 2-F, 3-F F 389,0 E1-86 (l-R-A). T1-33 / T2-24 / T3-1 2-CI, 3-cyclopropyl 2-F, 5-F F 410,9 E1-87 (l-R-A). T1-3 / T2-1 / T3-1 2-CI - F 335,0 E1-88 (l-R-A). T1-23 / T2-1 / T3-1 2-F, 3-F - F 337,0 E1-89 (l-R-A). T1-49 / T2-24 / T3-1 2-CECH, 3-F 2-F, 5-F F 391,0 E1-90 (l-R-A). T1-897 / T2-24 / T3-1 2-CI, 3-OCH3 2-F, 5-F F 401,0 E1-91 (l-R-A). T1-905 / T2-1 / T3-1 2-F, 3-O(3-OC2H5-Ph) - F 455,1 E1-92 (l-R-A). T1-903 / T2-1 / T3-1 2-F, 3-OC(CH3)3- F 391,2 E1-93 (l-R-A). T1-9 / T2-1 / T3-1 3-F - F 319,1

[0882]

[0883] E1-94 (l-R-A). T1-545 / T2-24 / T3-1 2-CI, 3-F, 6-F 2-F, 5-F F 407 BASF SE 241388

[0884] 57

[0885] ExamCompound N LCMS ple No. o R1R2R3

[0886] (M+H) E1-95 (l-R-A). T1-902 / T2-1 / T3-1 2-F, 3-C(CH3)3- F 375,2 E1-96 (l-R-A). T1-901 / T2-1 / T3-1 2-F, 3-(1 -piperidyl) - F 402,2 E1-97 (l-R-A). T1-900 / T2-1 / T3-1 2-F, 3-O(3-OCH3-Ph) - F 440,2 E1-98 (l-R-A). T1-899 / T2-1 / T3-1 2-F, 3-OPh - F 411 E1-99 (l-R-A). T1-898 / T2-1 / T3-1 2-F, 3-OC2H5 - F 363,1 E1-100 (l-R-A). T1-906 / T2-1 / T3-1 2-F, 3-OCH2-cyclopropyl 2-F, 5-F F 425,1 E1-101 (l-R-A). T1-195 / T2-24 / T3-1 2-F, 3-F, 4-F 2-F, 5-F F 391 E1-102 (l-R-A). T1-904 / T2-1 / T3-1 2-F, 3-O(3-OH-Ph) - F 425,2 E1-103 (l-R-A). T1-795 / T2-24 / T3-1 3-F, 4-F, 5-F 2-F, 5-F F 390,9 E1-104 (l-R-A). T1-445 / T2-24 / T3-1 2-F, 3-CI, 5-F 2-F, 5-F F 406,9 E1-105 (l-R-A). T1-196 / T2-24 / T3-1 2-F, 3-F, 4-CI 2-F, 5-F F 407 E1-106 (l-R-A). T1-203 / T2-24 / T3-1 2-F, 3-CI, 4-CI 2-F, 5-F F 423 E1-107 (l-R-A). T1-899 / T2-1 / T3-1 2-CI, 3-OCHF2 - F 401 E1-108 (l-R-A). T1-899 / T2-24 / T3-1 2-CI, 3-OCHF2 2-F, 5-F F 437 E1-109 (l-R-A). T1-246 / T2-24 / T3-1 2-F, 3-CI, 4-F 2-F, 5-F F 406 E1-110 (l-R-A). T1-898 / T2-24 / T3-1 2-F, 3-OS(O)2CH32-F, 5-F F 449 E1-111 (l-R-A). T1-907 / T2-1 / T3-1 3-SCF32-F, 5-F F 436,9 E1-112 (l-R-A). T1-138 / T2-1 / T3-1 3-F, 4-F - F 337 E1-113 (l-R-A). T1-62 / T2-1 / T3-1 2-CH3, 3-CI - F 349,2 E1-114 (l-R-A). T1-136 / T2-1 / T3-1 2-CH3, 6-CI - F 349,2 E1-115 (l-R-A). T1-897 / T2-1 / T3-1 2-CH3, 4-CH3- F 329,1 E1-116 (l-R-A). T1-891 / T2-1 / T3-1 2-F, 3-OCF2Br - F 463 E1-117 (l-R-A). T1-891 / T2-24 / T3-1 2-F, 3-OCF2Br 2-F, 5-F F 498,8 E1-118 (l-R-A). T1-895 / T2-1 / T3-1 2-CI, 4-OCF3- F 419 E1-119 (l-R-A). T1-896 / T2-1 / T3-1 2-F, 4-OCF3- F 403,1 E1-120 (l-R-A). T1-894 / T2-1 / T3-1 2-CI, 3-OCF2CI - F 435 E1-121 (l-R-A). T1-909 / T2-1 / T3-1 2-F, 3-(4-F-2-pyridyl) - F 414,1 E1-122 (l-R-A). T1-31 / T2-2 / T3-1 2-CI, 3-CI 2-F F 387 E1-123 (l-R-A). T1-62 / T2-3 / T3-1 2-CH3, 3-CI 2-CI F 382,9 E1-124 (l-R-A). T1-892 / T2-24 / T3-1 2-F, 3-OCF2CI 2-F, 5-F F 471 E1-125 (l-R-A). T1-894 / T2-24 / T3-1 2-CI, 3-OCF2CI 2-F, 5-F F 455 E1-126 (l-R-A). T1-892 / T2-1 / T3-1 2-F, 3-OCF2CI - F 419 E1-127 (l-R-A). T1-910 / T2-1 / T3-1 2-F, 3-(6-F-2-pyridyl) - F 414,1 E1-128 (l-R-A). T1-892 / T2-6 / T3-1 2-F, 3-OCF2CI 3-F F 437 E1-129 (l-R-A). T1-916 / T2-1 / T3-1 2-CI, 3-O-(CF2)-O-4 - F 415 E1-130 (l-R-A). T1-916 / T2-24 / T3-1 2-CI, 3-O-(CF2)-O-4 2-F, 5-F F 451,2 E1-131 (l-R-A). T1-911 / T2-1 / T3-1 2-F, 3-CH2-(CF2)-O-4 F 397,1

[0887]

[0888] E1-132 (l-R-A). T1-912 / T2-1 / T3-1 2-F, 3-O-(CF2)-CH2-4 - F 397,1

[0889] B. Use examples BASF SE 241388

[0890] 58

[0891] The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:

[0892] 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.

[0893] 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.

[0894] 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.

[0895] 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.

[0896] 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.

[0897] The test plants used in the greenhouse experiments were of the following species:

[0898] Bayer code Scientific name Bayer code Scientific name

[0899] ALOMY Alopercurus myosuroides ECHCG Echinocloa crus-galli AMARE Amaranthus retroflexus LOLMU Lolium multiflorum APESV Apera spica-venti POLCO Polygonum convolvulus AVEFA Avena fatua SETFA Setaria faberi

[0900] CHEAL Chenopodium album SETIT Setaria italica

[0901]

[0902] DIGSA Digitaria sanguinalis

[0903]

[0904] SETVI Setaria viridis

[0905] In Table U1 below good herbicidal activity is given at values of 70-89 (denoted as +) and a very good herbicidal activity is given at values of at least 90-100 (denoted as ++). BASF SE 241388

[0906] 59

[0907] LOLMU

[0908] Table U1 APESV post-emergence efficacy pre-emergence efficacy Compound applicaSETVI

[0909] from Example tion rate

[0910] No. (g / ha)

[0911] SETFA

[0912] E1-1 1000 ++

[0913] E1-6 500 ++ ++ + DIGSA+

[0914] E1-8 500 ++ ++ +

[0915] E1-10 500 ++ + ++ +

[0916] E1-11 500 ++ + + AMARE+ +

[0917] E1-12 500 ++ +

[0918] E1-14 500 ++ ++ ++ ++

[0919] ++ ++ POLCO

[0920] E1-15 500 ++ ++ ++

[0921] E1-16 500 ++ + ++ ++ ++

[0922] E1-18 500 ++ ++ ++ + +

[0923] ECHCG

[0924] E1-19 500 ++ + ++

[0925] E1-21 500 ++ + + +

[0926] E1-22 500 ++ AVEFA + ++ ++ ++

[0927] E1-23 500 ++ ++

[0928] E1-24 500 + + +

[0929] E1-25 500 AMARE + ++ ++ ++ ++

[0930] E1-26 500 + ++ ++

[0931] E1-27 500 ++ +

[0932] E1-29 500 ++ ++

[0933] E1-30 500 ++ + ++

[0934] E1-31 500 ++ + + +

[0935] E1-32 500 ++ ++ ++ +

[0936] E1-33 500 ++ ++ +

[0937] E1-34 500 ++ + ++ ++

[0938] E1-35 500 + + ++ ++ ++

[0939] E1-36 500 ++ +

[0940] E1-38 500 ++ ++

[0941] E1-46 500 ++ + ++

[0942] E1-47 500 ++ ++ ++ +

[0943] E1-91 500 ++ + E1-95 500 +

[0944] E1-96 500 + +

[0945] E1-101 500 + ++

[0946] E1-104 500 + ++

[0947] E1-107 500 + ++ +

[0948] E1-108 250 + + ++ ++ ++

[0949] E1-110 500 + + + + E1-111 500 + ++

[0950] E1-113 500 ++ ++ ++

[0951] E1-116 250 + + ++

[0952]

[0953] E1-117 250 + + BASF SE 241388

[0954] 60

[0955] LOLMU

[0956] post-emergence efficacy pre-emergence efficacy Compound applicafrom Example tion rate APESV No. (g / ha)

[0957] SETVI

[0958] E1-120 500 ++ +

[0959]

[0960] E1-125 250 ++ +

[0961] SETFA

[0962] Comparative examples

[0963] DIGSA

[0964] Table C1. Herbicidal activity in post-emergence treatment (POST) and pre-emergence treatment (PRE) AMARE

[0965] PRE, % POST, % Compound APESV SETIT SETIT,

[0966] POLCO 500 g / ha 500 g / ha 125 g / ha F

[0967] u i °c|P ECHCGresent

[0968] 90 100 90 invention

[0969] W A-sy

[0970] AVEFA F WO

[0971] M l0 ClAMARE 2001 / 046152,

[0972] 20 0 25 p.28, Table 3,

[0973] Example 182

[0974]

[0975] Table C2. Herbicidal activity in post-emergence treatment (POST)

[0976] POST, % Compound SETIT CHEAL POLCO 62 g / ha 125 g / ha 62 g / ha i— i i0 Cl

[0977] Vr’Ayr" Present invention 85 not tested 90

[0978] Present invention 70 85 95

[0979] WO

[0980] 2001 / 046152,

[0981] 20 0 45 p.28, Table 3,

[0982]

[0983] Example 197

[0984] Table C3. Herbicidal activity in post-emergence treatment (POST) BASF SE 241388

[0985] 61

[0986] POST, %

[0987] Compound AMARE POLCO

[0988] 62 g / ha 250 g / ha i— i i °Cl

[0989] Present invention not tested 85

[0990] Cl OH

[0991] CI'Y< Xii H 1 °Cl

[0992] C, Present invention 70 85

[0993] Cl 0H

[0994] M 10 ClWO

[0995] 2001 / 046152,

[0996] 20 35

[0997] p.28, Table 3,

[0998] Cl OHExample 198

[0999]

[1000] Table C4. Herbicidal activity in post-emergence treatment (POST) and pre-emergence treatment (PRE)

[1001] PRE, % POST, % Compound AMARE POLCO

[1002] 250 g / ha 500 g / haFV^i i— i!0CH3

[1003] Present invention 85 75

[1004] f^l) M 10 ClWO

[1005] 2001 / 046152,

[1006] 0 30

[1007] p.29, Table 3,

[1008] Example 214

[1009]

Claims

BASF SE 24138862Claims1. A compound of formula I5whereinZ is phenyl;R1each is independently selected from halogen, CN, NO2, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, C2-Ce-haloalkenyl, C2-Ce-haloalkynyl, Cs-Ce-cycloal- kyl, Cs-Ce-halocycloalkyl, Cs-Ce-cycloalkoxy, Ci-Ce-alkoxy, C2-Ce-alkenyloxy, C2-C6- alkynyloxy, Ci-Ce-haloalkoxy, C2-C6-haloalkenyloxy, C2-Ce-haloalkynyloxy, Ci-Ce- alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxy-Ci-Ce-alkoxy, Ci-Ce-alkylcarbonyl, Ci-Ce-alkylcar- bonyloxy, hydroxycarbonyl, Ci-Ce-alkoxycarbonyl, Ci-Ce-alkylaminocarbonyl, di(Ci- C6-alkyl)aminocarbonyl, NH2, (Ci-Ce-alkyl)amino, di(Ci-Ce-alkyl)amino, Ci-Ce-al- kylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, Ci-Ce-haloalkylthio, Ci-Ce-haloalkyl- sulfinyl, Ci-Ce-haloalkylsulfonyl, Ci-Ce-alkylaminosulfinyl, di(Ci-C6-alkyl)aminosulfi- nyl, Ci-Ce-alkylaminosulfonyl, di(Ci-C6-alkyl)aminosulfonyl, halosulfonyl, phenoxy, phenyl or 4- to 6-membered saturated or unsaturated heterocyclyl having 1, 2 or 3 heteroatoms or heteroatom moieties, selected from O, S, SO, SO2, N or NR12as ring members;or two adjacent R1together with the carbon atoms to which they are attached form a fused saturated 5- to 7-membered heterocycle having 1 or 2 heteroatoms or heteroatom moieties, selected from O, S, N or NR12as ring memberswherein the aliphatic or aromatic groups of R1or a fused heterocycle are unsubstituted or substituted with 1 or 2 the same or different substituents R11;R11is selected from halogen, CN, NO2, NH2, NHR12, NR12R13, Ci-C6-alkyl, C2-C6-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, C2-Ce-haloalkenyl, C2-Ce-haloalkynyl, Ci-Ce-alkoxy, C2-Ce-alkenyloxy, C2-Ce-alkynyloxy, Ci-Ce-haloalkoxy, C2-Ce-haloalkenyloxy, C2-C6- haloalkynyloxy, or Si(CH₃)₃;BASF SE 24138863R12is selected from Ci-Ce-alkyl, C2-C6-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, C2-C6- haloalkenyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-Ce-alkyl- carbonyl, Ci-Ce-alkoxycarbonyl, Ci-Ce-alkylaminocarbonyl, di(Ci-Ce-alkyl)aminocar- bonyl, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, or Ci-Ce-alkylsulfonyl;R13is selected from Ci-Ce-alkyl, C2-C6-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, C2-C6- haloalkenyl, C2-C6-haloalkynyl, C3-Ce-cycloalkyl, C3-Ce-halocycloalkyl, Ci-Ce-alkyl- carbonyl, Ci-Ce-alkoxycarbonyl, Ci-Ce-alkylaminocarbonyl, di(Ci-Ce-alkyl)aminocar- bonyl, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, or Ci-Ce-alkylsulfonyl;n is 0, 1, 2, or 3;R2each is independently selected from halogen, CN, NO2, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, C2-C6-haloalkenyl, C2-Ce-haloalkynyl, C3-Ce-cycloal- kyl, C3-Ce-halocycloalkyl, C3-Ce-cycloalkoxy, Ci-Ce-alkoxy, C2-Ce-alkenyloxy, C2-C6- alkynyloxy, Ci-Ce-haloalkoxy, C2-C6-haloalkenyloxy, C2-C6-haloalkynyloxy;wherein the aliphatic groups of R2are unsubstituted or substituted with one or two the same or different substituents R21;R21is selected from halogen, CN, NO2, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce- haloalkyl, C2-C6-haloalkenyl, C2-Ce-haloalkynyl, Ci-Ce-alkoxy, C2-Ce-alkenyloxy, C2- Ce-alkynyloxy, Ci-Ce-haloalkoxy, C2-C6-haloalkenyloxy, C2-C6-haloalkynyloxy, or Si(CH3)3;m is 0, 1, 2, or 3;R3is selected from halogen, CN, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-Ce- haloalkyl, C2-Ce-haloalkenyl, C2-Ce-haloalkynyl, Ci-Ce-alkoxy, C2-Ce-alkenyloxy, C2- Ce-alkynyloxy, Ci-Ce-haloalkoxy, C2-Ce-haloalkenyloxy, or C2-Ce-haloalkynyloxy;provided that when Z is phenyl bearing substituents R1at the 2- and 3-position with respect to the attachment point of the phenyl to the remainder of the molecule and R1at the 2-position is F, then R1at the 3-position is not OCF3; andprovided that when n = 1, m = 0 and R1is at the 4-position with respect to the attachment point of the phenyl to the remainder of the molecule, then if R1is Br, R3is not Br and if R1is NO2, R3is not NO2and its stereoisomers, tautomers, and agriculturally accepted salts.

2. The compound according to claim 1, wherein R3is selected from halogen or CN.BASF SE 241388643. The compound according to claim 1 or claim 2, wherein R3is halogen.

4. The compound according to any of the claims 1 to 3, wherein n is 1, 2 or 3.

5. The compound according to any of the claims 1 to 4, n is 2 or 3.

6. The compound according to any of the claims 1 to 5, wherein R1each is independently selected from halogen, CN, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2- C4-haloalkynyl, Cs-cycloalkyl, Cs-halocycloalkyl, C3- cycloalkoxy, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci-C4-alkylcarbonyloxy, (Ci-C4-alkyl)amino, di(Ci-C4-alkyl)amino, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, halosul- fonyl, phenoxy, phenyl or 6-membered saturated or unsaturated heterocyclyl having 1 or 2 heteroatoms or heteroatom moieties, selected from O, N or NR12as ring members..

7. The compound according to any one of the claims 1 to 6, wherein R2is halogen.

8. The compound according to any one of the claims 1 to 7, wherein m is 0 or 1.

9. The compound according to any one of the claims 1 to 8, that is the isomer I-R10. The compound according to any one of the claims 1 to 8, that is the isomer I-S511. An agrochemical composition comprising a herbicidally active amount of a compound of formula I as defined in any one of the claims 1 to 10 and at least one inert liquid or solid carrier and, if appropriate, at least one surface-active substance.BASF SE 2413886512. A method for controlling undesired vegetation which comprises allowing a herbicidally effective amount of a compound of formula I as defined in any one of the claims 1 to 10, or a composition as defined in claim 11 to act on plants, their seed and / or their habitat.

13. Use of a compound of formula I as defined in any one of claims 1 to 10, or a composition as defined in claim 11 for controlling undesired vegetation.

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