Herbicidal pyridyl ethers

Abstract

The present invention relates to pyridyl ethers of formula (I) or agriculturally acceptable salts or derivatives thereof, wherein the variables are defined according to the description, processes and intermediates for preparing pyridyl ethers of formula (I), compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted plant growth, comprising subjecting a herbicidally effective amount of at least one pyridyl ether of formula (I) to the action on plants, their seeds and / or the land on which they grow.

Description

[0001] The invention relates to pyridyl ethers of the general formula (I) as defined below and to their use as herbicides. Furthermore, the invention relates to crop protection compositions and a method for controlling unwanted vegetation.

[0002] WO 88 / 01133 and WO 98 / 41093 describe structurally similar compounds having a central benzene ring, whereas the compounds of the present invention feature a central pyridine ring.

[0003] However, the herbicidal properties of these known compounds against harmful plants are not always completely satisfactory.

[0004] The object of the present invention is therefore to provide pyridyl ethers of the formula (I) with improved herbicidal action. In particular, pyridyl ethers of the formula (I) are to be provided which have high herbicidal activity, in particular even at low application rates, and are fully compatible with commercially exploited crops.

[0005] These and other objects are achieved by the pyridyl ethers of the formula (I) defined below and their agriculturally acceptable salts.

[0006] Therefore, the present invention provides pyridyl ethers of formula (I):

[0007]

[0008] The substituents have the following meanings:

[0009] R 1 is H or halogen;

[0010] R 2 is H, halogen, CN, NO2, NH2, CF3 or C(=S)NH2;

[0011] R 3 is H, halogen, CN, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylamino, di-C1-C3 alkylamino, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxycarbonyl;

[0012] R 4 is H, halogen, C1-C3 alkyl, C1-C3 alkoxy;

[0013] R 5 OR 6 , SR 6 NR 7 R 8 NR 6 OR 6 NR 6 S(O)2R7 or NR 6 S(O)2NR 7 R 8 ,in

[0014] R 6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C3-C6 haloalkenyl, C3-C6 haloalkynyl, C1-C6 cyanoalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkoxy-C1-C6 alkyl, di(C1-C6 alkoxy)C1-C6 alkyl, C1-C6 haloalkoxy-C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkyl, C3-C6 haloalkenyloxy-C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl, C1-C6 alkylsulfinyl-C1-C6 alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-haloalkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, amino, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylcarbonylamino, amino-C1-C6-alkyl, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, aminocarbonyl-C1-C6-alkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkyl, di-C1-C6-alkylaminocarbonyl-C1-C6-alkyl,

[0015] -N=CR 9 R 10 , where R 9 and R 10 are independently H, C1-C4 alkyl or phenyl;

[0016] C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 heterocyclic group, C3-C6 heterocyclic group

[0017] -C1-C6 alkyl, phenyl, phenyl-C1-C4 alkyl or 5- or 6-membered heteroaryl,

[0018] wherein the cycloalkyl, heterocyclyl, phenyl or heteroaryl rings can each be substituted by 1 to 4 groups selected from R 13 or a 3-7 membered carbon ring substituent,

[0019] The carbocyclic ring optionally has, in addition to the carbon atoms, 1 or 2 selected from -N(R 9)-、-N=N-、-C(=O)-、

[0020] -O- and -S- ring members, and

[0021] The carbon ring is optionally substituted by 1 to 4 groups selected from R 11 Substituents are substituted;

[0022] Where R 11 is halogen, NO2, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 alkoxycarbonyl;

[0023] R 7 , R 8 Independently of each other, R 6 , or together form a 3-7 member carbon ring,

[0024] The carbocyclic ring optionally has, in addition to the carbon atoms, 1 or 2 selected from -N(R 9 )-、-N=N-、

[0025] -C(=O)-, -O- and -S- ring members, and

[0026] The carbon ring is optionally substituted by 1 to 4 groups selected from R 11 Substituents are substituted;

[0027] n is 1-3;

[0028] Q is O, S, SO, SO2, NH or (C1-C3 alkyl)N;

[0029] W is O or S;

[0030] X is O or S;

[0031] Y is selected from Y 1 -Y 76 , preferably Y 1 -Y 75 Heterocyclic ring:

[0032]

[0033]

[0034]

[0035]

[0036] in

[0037] A 1 , A 2 , A 3 is oxygen or sulfur;

[0038] A 4 Oxygen, sulfur, SO or SO2;

[0039] R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 is hydrogen, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkenoxy, C3-C6 alkynyl, C3-C6 alkynyloxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkoxysulfonyl, C1-C6 alkylsulfonyloxy, amino, C1-C6 alkylamino or di(C1-C6 alkyl)amino; or

[0040] R 12 and R 13 Together with the atoms to which they are attached, they form a 3-6 membered ring, which is saturated, partially unsaturated or aromatic, which, in addition to carbon atoms, may contain 1 to 4 nitrogen atoms, or 1 or 2 oxygen atoms, or 1 or 2 sulfur atoms, or 1 to 3 nitrogen atoms and 1 oxygen atom, or 1 to 3 nitrogen atoms and 1 sulfur atom, or 1 sulfur and 1 oxygen atom, and which itself may be partially or fully halogenated and / or substituted by 1 to 3 groups selected from C1-C6 alkyl and C1-C6 alkoxy;

[0041] R 19 , R 20 , R 21 , R 22 , R 23 , R 24 is hydrogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 cyanoalkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkenoxy, C3-C6 alkynyl, C3-C6 alkynyloxy, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, phenyl-C1-C6 alkyl, amino, C1-C6-alkylamino or di(C1-C6 alkyl)amino; or

[0042] R 21 and R 22Together with the atoms to which they are attached, they form a 3-6 membered ring, which is saturated, partially unsaturated or aromatic, which, in addition to carbon atoms, may contain 1 to 4 nitrogen atoms, or 1 or 2 oxygen atoms, or 1 or 2 sulfur atoms, or 1 to 3 nitrogen atoms and 1 oxygen atom, or 1 to 3 nitrogen atoms and 1 sulfur atom, or 1 sulfur and 1 oxygen atom, and which itself may be partially or fully halogenated and / or substituted by 1 to 3 groups selected from C1-C6 alkyl and C1-C6 alkoxy;

[0043] R 25 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C6-alkynyl, C1-C6-haloalkoxy, amino, C1-C6-alkylamino or di(C1-C6-alkyl)amino;

[0044] R 26 and R 27 is hydrogen, halogen or C1-C6 alkyl;

[0045] R 28 , R 29 and R 30 is hydrogen, halogen, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkenoxy, C3-C6 alkynyl or C3-C6 alkynyloxy; and

[0046] R 31 is hydrogen, NH2, C1-C6 alkyl or C3-C6 alkynyl;

[0047] R 32 , R 33 and R 34 is hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkenoxy, C3-C6 alkynyl, C3-C6 alkynyloxy, C1-C6 alkoxycarbonyl, C2-C6 alkenylthio, C3-C6 alkynylthio, C1-C6 alkylamino, di(C1-C6 alkyl)amino or C3-C7 cycloalkyl-C1-C3 alkyl;

[0048] R 35 and R 36is hydrogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C6 alkynyl, C1-C6 alkoxycarbonyl, amino, C1-C6 alkylamino, di(C1-C6 alkyl)amino, C3-C7 cycloalkyl-C1-C3 alkyl, phenyl or phenyl-C1-C6 alkyl;

[0049] Z is phenyl, pyridyl, pyridazinyl, pyrimidinyl or pyrazinyl,

[0050] Each of which is optionally substituted with 1-4 substituents selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy;

[0051] Agriculturally acceptable salts or derivatives thereof are included, provided that the compound of formula (I) has a carboxyl group.

[0052] The present invention also provides an agrochemical composition comprising at least one pyridyl ether of the formula (I) and an adjuvant commonly used in formulating crop protection agents.

[0053] The present invention also provides a herbicidal composition comprising at least one pyridyl ether of the formula (I) (component A) and at least one further compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C).

[0054] The present invention also provides the use of the pyridyl ethers of formula (I) as herbicides, ie for controlling harmful plants.

[0055] In addition, the present invention provides a method for controlling unwanted plant growth, wherein a herbicidally effective amount of at least one pyridyl ether of formula (I) is applied to plants, their seeds and / or their habitat. Application can be carried out before, during and / or after, preferably during and / or after, the emergence of the unwanted plants.

[0056] Furthermore, the present invention relates to processes and intermediates for the preparation of pyridyl ethers of formula (I).

[0057] Further embodiments of the invention are apparent from the claims, the description and the examples. It is also understood that the features of the subject matter of the invention mentioned above and still to be explained below can be used not only in the combination given in each specific case but also in other combinations without departing from the scope of the invention.

[0058] As used herein, the terms "control" and "prevention" are synonymous.

[0059] As used herein, the terms "undesirable vegetation" and "harmful plants" are synonymous.

[0060] If the pyridyl ethers of the formula (I), the herbicidal compounds B and / or the safeners C described herein are capable of forming geometrical isomers, for example E / Z isomers, both the pure isomers and their mixtures can be used in the compositions according to the invention.

[0061] If the pyridyl ethers of the formula (I), the herbicidal compounds B and / or the safeners C described herein have one or more chiral centers and therefore exist as enantiomers or diastereomers, it is possible to use both the pure enantiomers and diastereomers and also mixtures thereof in the compositions according to the invention.

[0062] If the pyridyl ethers of formula (I), herbicidal compounds B and / or safeners C described herein have ionizable functional groups, they can also be used in the form of their agriculturally acceptable salts. Suitable are generally salts of those cations and acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.

[0063] Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium, ions of alkaline earth metals, preferably calcium and magnesium, and ions of transition metals, preferably manganese, copper, zinc and iron, furthermore ammonium and substituted ammonium in which 1 to 4 hydrogen atoms are replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diiso ... ammonium, trimethylammonium, triethylammonium, triisopropylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (alcoholamine salt), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tri(2-hydroxyethyl)ammonium (triolamine salt), tri(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), in addition ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxide ions, preferably tri(C1-C4-alkyl)sulfoxide, and finally salts of polyamines, such as N,N-di(3-aminopropyl)methylamine and diethylenetriamine.

[0064] Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, hydrogencarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.

[0065] The pyridyl ethers of formula (I) having a carboxyl group, the herbicidal compounds B and / or the safeners C described herein may be in the form of an acid, in the form of an agriculturally acceptable salt as described above or in the form of an agriculturally acceptable derivative, for example as an amide, such as a mono- and di-C1-C6-alkylamide or an arylamide, as an ester, for example as an allyl ester, a propargyl ester, a C1-C6-alkylamide or a C1-C6-alkylamide. 10 Alkyl esters, alkoxyalkyl esters, tetrahydrofuranylmethyl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as C1-C 10 Alkylthio esters are used. Preferred mono- and di-C1-C6 alkylamides are methyl and dimethylamides. Preferred arylamides are, for example, benzamide and 2-chlorobenzamide. Preferred alkyl esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, methylhexyl (1-methylhexyl), methylheptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred C1-C4 alkoxy-C1-C4 alkyl esters are straight-chain or branched C1-C4 alkoxyethyl esters, for example 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butoxyethyl), 2-butoxypropyl or 3-butoxypropyl esters. Straight-chain or branched C1-C 10 An example of an alkylthio ester is ethylthio ester.

[0066] In the variable R 3 -R 36 and R a -R e The organic moieties mentioned in the definition of are collective terms for the individual group members, just like the term halogen. The term halogen denotes in each case fluorine, chlorine, bromine or iodine. All hydrocarbon chains, such as all alkyl, alkenyl, alkynyl, alkoxy chains, which may be straight-chain or branched, are prefixed with C n -C m In each case the possible number of carbon atoms in the group is indicated.

[0067] Examples of this class meaning are:

[0068] -C1-C3-alkyl and also C1-C3-alkyl moieties of di-C1-C3-alkylamino, C1-C3-alkoxy-C1-C3-alkyl: for example CH3, C2H5, n-propyl and CH(CH3)2;

[0069] - C1-C4-alkyl and also C1-C4-alkyl moieties of phenyl-C1-C4-alkyl: for example CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, CH(CH3)-C2H5, CH2-CH(CH3)2 and C(CH3)3;

[0070] -C1-C6 alkyl and also C1-C6 cyanoalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkoxy-C1-C6 alkyl, di-C1-C6 alkoxy-C1-C6 alkyl, C1-C6 haloalkoxy-C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkyl, C3-C6 haloalkenyloxy

[0071] -C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio

[0072] -C1-C6 alkyl, C1-C6 alkylsulfinyl-C1-C6 alkyl, C1-C6 alkylsulfonyl-C1-C6 alkyl, C1-C6 alkylcarbonyl-C1-C6 alkyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl, C1-C6 haloalkoxycarbonyl-C1-C6 alkyl, C3-C6 alkenyloxycarbonyl-C1-C6 alkyl, C3-C6 alkynyloxycarbonyl-C1-C6 alkyl, C1-C6 alkylcarbonylamino, amino-C1-C6 alkyl, C1-C6 alkylamino

[0073] -C1-C6 alkyl, di-C1-C6 alkylamino-C1-C6 alkyl, aminocarbonyl-C1-C6 alkyl, C1-C6 alkylaminocarbonyl-C1-C6 alkyl, di-C1-C6 alkylaminocarbonyl-C1-C6 alkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 heterocyclyl-C1-C6 alkyl: C1-C4 alkyl as described above and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl 1-ethyl-2-methylpropyl, 1-ethyl-1-methylpropyl, ...1-methylpropyl, 1-ethyl-2-methylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1-ethyl-1-methylpropyl,

[0074] -C1-C3 haloalkyl: C1-C3 alkyl as described above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-fluoromethyl-2-fluoroethyl, 1-chloromethyl-2-chloroethyl, 1-bromomethyl-2-bromoethyl;

[0075] -C1-C4-haloalkyl: C1-C4-alkyl as described above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2 -fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-fluoromethyl-2-fluoroethyl, 1-chloromethyl-2-chloroethyl, 1-bromomethyl-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 1,1,2,2-tetrafluoroethyl and 1-trifluoromethyl-1,2,2,2-tetrafluoroethyl;

[0076] - C1-C6-haloalkyl: C1-C4-haloalkyl as described above and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;

[0077] -C3-C6-alkenyl and also C3-C6-alkenyloxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkoxy-C1-C6-alkyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl: for example 1-propenyl, 2-propenyl, 1-methylvinyl, 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-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3- dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

[0078] -C3-C6-haloalkenyl and also C3-C6-haloalkenyl moieties of C3-C6-haloalkenyloxy-C1-C6-alkyl: C3-C6-alkenyl as described above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, for example 2-chloroprop-2-en-1-yl, 3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop- 2-en-1-yl, 2,3,3-trichloroprop-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromoprop-2-en-1-yl or 2,3-dibromobut-2-en-1-yl;

[0079] -C3-C6-alkynyl and also C3-C6-alkynyloxycarbonyl-C1-C6-alkyl C3-C6-alkynyl moieties: for example 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl- 2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

[0080] - C3-C6 haloalkynyl: C3-C6 alkynyl as described above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, for example 1,1-difluoroprop-2-yn-1-yl, 3-chloroprop-2-yn-1-yl, 3-bromoprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;

[0081] - C1-C3 alkoxy and also C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxycarbonyl C1-C3 alkoxy moieties: for example methoxy, ethoxy, propoxy;

[0082] - C1-C4-alkoxy and also C1-C4-alkoxycarbonyl C1-C4-alkoxy moieties such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;

[0083] -C1-C6-alkoxy and also C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, di-C1-C6-alkoxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl C1-C6-alkoxy moieties: C1-C4-alkoxy as described above and also, for example, pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxybutoxy, 1,1-dimethylpropoxy, 1,2- dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy.

[0084] -C1-C3 haloalkoxy: a C1-C3 alkoxy group as described above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2- ... 2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-fluoromethyl-2-fluoroethoxy, 1-chloromethyl-2-chloroethoxy, 1-bromomethyl-2-bromoethoxy;

[0085] -C1-C4-haloalkoxy: C1-C4-alkoxy as described above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy 1-fluoromethyl-2-fluoroethoxy, 1-chloromethyl-2-chloroethoxy, 1-bromomethyl-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, and nonafluorobutoxy;

[0086] - C1-C6-haloalkoxy and also the C1-C6-haloalkoxy moieties of C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-haloalkoxycarbonyl-C1-C6-alkyl: C1-C4-haloalkoxy as described above and also, for example, 5-fluoropentyloxy, 5-chloropentyloxy, 5-bromopentyloxy, 5-iodopentyloxy, undecafluoropentyloxy, 6-fluorohexyloxy, 6-chlorohexyloxy, 6-bromohexyloxy, 6-iodohexyloxy and dodecafluorohexyloxy;

[0087] -C1-C3 alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio;

[0088] - C1-C4-alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio;

[0089] -C1-C6-alkylthio and also the C1-C6-alkylthio moiety of C1-C6-alkylthio-C1-C6-alkyl: C1-C4-alkylthio as described above and also, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio , 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;

[0090] -C1-C6-alkylsulfinyl (C1-C6-alkyl-S(═O)—) and also the C1-C6-alkylsulfinyl moieties of C1-C6-alkylsulfinyl-C1-C6-alkyl: for example methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethyl methylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl;

[0091] -C1-C6-alkylsulfonyl (C1-C6-alkyl-S(O)2-) and also C1-C6-alkylsulfonyl moieties of C1-C6-alkylsulfonyl-C1-C6-alkyl: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1- ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

[0092] - C1-C3 alkylamino: for example methylamino, ethylamino, propylamino, 1-methylethylamino;

[0093] - C1-C4-alkylamino: for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino or 1,1-dimethylethylamino;

[0094] -C1-C6-alkylamino: C1-C4-alkylamino as described above and also, for example, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethyl-propylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;

[0095] - di-C1-C6-alkylamino: di-C1-C4-alkylamino as described above and also, for example, N-methyl-N-pentylamino, N-methyl-N-(1-methylbutyl)amino, N-methyl-N-(2-methylbutyl)amino, N-methyl-N-(3-methylbutyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1-ethylpropyl)amino, N-methyl-N-hexylamino, N-methyl-N-(1,1-dimethylpropyl)amino, N-methyl-N-(1,2-dimethylpropyl)amino, N-methyl-N-(1-methylpentyl)amino, N-methyl-N-(2-methylpentyl)amino, N-methyl-N- (3-methylpentyl)amino, N-methyl-N-(4-methylpentyl)amino, N-methyl-N-(1,1-dimethylbutyl)amino, N-methyl-N-(1,2-dimethylbutyl)amino, N-methyl-N-(1,3-dimethylbutyl)amino, N-methyl-N-(2,2-dimethylbutyl)amino, N-methyl-N-(2,3-dimethylbutyl)amino, N-methyl-N-(3,3-dimethylbutyl)amino, N-methyl-N-(1-ethylbutyl)amino, N-methyl-N-(2-ethylbutyl)amino, N-methyl-N-(1,1,2-trimethylpropyl)amino, N-methyl-N-(1,2,2-trimethylpropyl)amino, N-methyl-N-(1-ethyl-1-methylpropyl)amino, N-methyl-N-(1-ethyl-2-methylpropyl)amino, N-ethyl-N-pentylamino, N-ethyl-N-(1-methylbutyl)amino, N-ethyl-N-(2-methylbutyl)amino, N-ethyl-N-(3-methylbutyl)amino, N-ethyl-N-(2,2-dimethylpropyl)amino, N-ethyl-N-(1-ethylpropyl)amino, N-ethyl-N-hexylamino, N-ethyl-N-(1,1-dimethylpropyl)amino, N-ethyl-N-(1,2-dimethylpropyl)amino, N-ethyl-N-(1-methylpentyl)amino, N-ethyl-N-(2-methylpentyl)amino )amino, N-ethyl-N-(3-methylpentyl)amino, N-ethyl-N-(4-methylpentyl)amino, N-ethyl-N-(1,1-dimethylbutyl)amino, N-ethyl-N-(1,2-dimethylbutyl)amino, N-ethyl-N-(1,3-dimethylbutyl)amino, N-ethyl-N-(2,2-dimethylbutyl)amino, N-ethyl-N-(2,3-dimethylbutyl)amino, N-ethyl-N-(3,3-dimethylbutyl)amino, N-ethyl-N-(1-ethylbutyl)amino, N-ethyl-N-(2-ethylbutyl)amino, N-ethyl-N-(1,1,2-trimethylpropyl)amino, N-ethyl-N-(1,2,2-trimethylpropyl)amino, N-ethyl-N-(1-ethyl-1-methylpropyl)amino, N-ethyl-N-(1-ethyl-2-methylpropyl)amino, N-propyl-N-pentylamino, N-butyl-N-pentylamino, N,N-dipentylamino, N-propyl-N-hexylamino, N-butyl-N-hexylamino, N-pentyl-N-hexylamino or N,N-dihexylamino;

[0096] - C3-C6-cycloalkyl and also the cycloalkyl moieties of C3-C6-cycloalkyl-C1-C6-alkyl: monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

[0097] -C3-C6-heterocyclyl and also the heterocyclyl moiety of C3-C6-heterocyclyl-C1-C6-alkyl: an aliphatic heterocycle having 3 to 6 ring members which, in addition to carbon atoms, contains 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and oxygen or sulfur atoms or oxygen or sulfur atoms, for example

[0098] 3- or 4-membered heterocyclic rings, such as 2-oxetanyl, 3-oxetanyl, 2-thietanyl, 3-thietanyl, 1-azetidinyl, 2-azetidinyl, 1-azetidinyl, 2-azetidinyl; 5-membered saturated heterocyclic rings, such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isothienyl; Oxazolidinyl, 4-iso Oxazolidinyl, 5-iso oxazolidinyl, 2-isothiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2- Oxazolidinyl, 4- Oxazolidinyl, 5- oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 3- Oxazolidinyl, 1,2,4- oxadiazolidine-3-yl, 1,2,4- 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,2,4- oxadiazolidine-2-yl, 1,2,4- oxadiazolidine-4-yl, 1,3,4- 1,2,4-thiadiazolidin-2-yl, 1,2,4-thiadiazolidin-4-yl, 1,3,4-thiadiazolidin-2-yl, 1,2,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl; 6-membered saturated heterocyclic rings such as 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxadiazolidine-2-yl, 1,2,4-thiadiazolidin-2-yl, 1,2,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl; Alk-5-yl, 1,4-di alkyl, 1,3-dithian-5-yl, 1,3-dithianyl, 1,3-oxathian-5-yl, 1,4-oxathianyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 1-hexahydropyridazinyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 1-hexahydropyrimidinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 1-piperazinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-1-yl, 1,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-1-yl, 1,2,4-hexahydrotriazin-3-yl, tetrahydro-1,3- Oxazine-1-yl, tetrahydro-1,3- Oxazine 2-yl, tetrahydro-1,3- Oxazine-6-yl, 1-morpholinyl, 2-morpholinyl, 3-morpholinyl;

[0099] -5- or 6-membered heteroaryl: an aromatic heteroaryl having 5 or 6 ring members which, in addition to carbon atoms, contains 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and oxygen or sulfur atoms or oxygen or sulfur atoms, for example a 5-membered aromatic ring such as furyl (e.g. 2-furyl, 3-furyl), thienyl (e.g. 2-thienyl, 3-thienyl), pyrrolyl (e.g. pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (e.g. pyrazol-3-yl, pyrazol-4-yl), isothiocyanate (e.g. pyrazol-2-yl, pyrazol-3-yl), isothiocyanate (e.g. pyrazol-4-yl), isothiocyanate (e.g. pyrazol-5-yl, pyrazol-6-yl), isothiocyanate (e.g. pyrazol-6-yl, pyrazol-7-yl), isothiocyanate (e.g. pyrazol-7-yl, pyrazol-8-yl), isothiocyanate (e.g. pyrazol-8-yl, pyrazol-9-yl), isothiocyanate (e.g. pyrazol-10-yl, pyrazol-11-yl), isothiocyanate (e.g. pyrazol-10-yl, pyrazol-12-yl), isothiocyanate (e.g. pyrazol-10-yl, pyrazol-13-yl), isothiocyanate (e.g. pyrazol-10-yl, pyrazol-14-yl), isothiocyanate (e.g. pyrazol-10-yl, pyrazol-13-yl), isothiocyanate (e.g. pyrazol-10 Azolyl (e.g. Oxazol-3-yl, iso Oxazol-4-yl, iso oxazol-5-yl), isothiazolyl (e.g., isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl (e.g., imidazol-2-yl, imidazol-4-yl), Azolyl (e.g. Oxazol-2-yl, Oxazol-4-yl, oxazol-5-yl), thiazolyl (e.g. thiazol-2-yl, thiazol-4-yl, thiazol-5-yl), Oxazolyl (e.g. 1,2,3- oxadiazole-4-yl, 1,2,3- oxadiazole-5-yl, 1,2,4- oxadiazole-3-yl, 1,2,4- oxadiazole-5-yl, 1,3,4- 1,2,3-thiazol-4-yl, 1,2,3-thiazol-5-yl, 1,2,4-thiazol-3-yl, 1,2,4-thiazol-5-yl, 1,3,4-thiazol-2-yl), triazolyl (e.g. 1,2,3-triazol-4-yl, 1,2,4-triazol-3-yl); 1-tetrazolyl; 6-membered aromatic rings such as pyridyl (e.g. pyridin-2-yl, pyridin-3-yl, pyridin-4-yl), pyrazinyl (e.g. pyridazin-3-yl, pyridazin-4-yl), pyrimidinyl (e.g. pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl), pyrazin-2-yl, triazinyl (e.g. 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl);

[0100] -3-7 membered carbocyclic ring: a 3-7 membered monocyclic, saturated, partially unsaturated or aromatic ring having 3-7 ring members, which, in addition to carbon atoms, optionally contains 1 or 2 atoms selected from -N(R 12 )-, -N=N-, -C(=O)-, -O-, and -S- ring members.

[0101] The preferred embodiments of the invention described below are to be understood as being preferred either independently of one another or in combination with one another.

[0102] According to a preferred embodiment of the invention, preference is also given to those pyridyl ethers of the formula (I) in which the variables, independently of one another or in combination with one another, have the following meanings:

[0103] Pyridyl ethers of the following formula (I) are preferred, wherein R 1 is H, F or Cl; is particularly preferably H or F; is particularly preferably H; is also particularly preferably H or Cl; is particularly preferably Cl; is also particularly preferably F or Cl; is particularly preferably F.

[0104] Also preferred are pyridyl ethers of the formula (I) wherein R 2 is halogen or CN; preferably F, Cl, Br or CN; particularly preferably F, Cl or CN; especially preferably Cl or CN; more preferably Cl; still more preferably CN; still more preferably F or Cl; more preferably F.

[0105] Also preferred are pyridyl ethers of the formula (I) wherein R 3It is H, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio; particularly preferably H, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 alkoxy; especially preferably H, C1-C3 alkyl or C1-C3 alkoxy; more preferably H, CH3 or OCH3.

[0106] Also preferred are pyridyl ethers of formula (I) wherein R 4 It is H, halogen or C1-C3 alkyl; particularly preferably H, F or CH3; especially preferably H.

[0107] Also preferred are pyridyl ethers of formula (I) wherein R 5 OR 6 , SR 6 NR 7 R 8 NR 6 S(O)2R 7 or NR 6 S(O)2NR 7 R 8 ; OR is particularly preferred 6 NR 7 R 8 NR 6 S(O)2R 7 or NR 6 S(O)2NR 7 R 8 ; OR is particularly preferred 6 NR 6 S(O)2R 7 or NR 6 S(O)2NR 7 R 8 ; OR is particularly preferred 6 or NR 6 S(O)2R 7 .

[0108] Also preferred are pyridyl ethers of formula (I), wherein

[0109] R 6is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C3-C6 haloalkenyl, C3-C6 haloalkynyl, C1-C6 cyanoalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkoxy-C1-C6 alkyl, di(C1-C6 alkoxy)C1-C6 alkyl, C1-C6 haloalkoxy-C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkyl, C3-C6 haloalkenyloxy-C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl, C1-C6 alkylsulfinyl-C1-C6 alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-haloalkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, amino, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylcarbonylamino, amino-C1-C6-alkyl, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, aminocarbonyl-C1-C6-alkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkyl, di-C1-C6-alkylaminocarbonyl-C1-C6-alkyl,

[0110] -N=CR 9 R 10 ,

[0111] Where R 9 and R 10 are independently H, C1-C4 alkyl or phenyl;

[0112] C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 heterocyclyl, phenyl, phenyl-C1-C4 alkyl or 5- or 6-membered heteroaryl,

[0113] wherein the cycloalkyl, heterocyclyl, phenyl or heteroaryl rings can each be substituted by 1 to 4 groups selected from R 11 or a 3-7 membered carbon ring substituent,

[0114] The carbocyclic ring optionally has, in addition to the carbon atoms, 1 or 2 selected from -N(R 9 )-、-N=N-、-C(=O)-、

[0115] -O- and -S- ring members, and

[0116] The carbon ring is optionally substituted by 1 to 4 groups selected from R 11 Substituents are substituted,

[0117] Where R 11 is halogen, NO2, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 alkoxycarbonyl;

[0118] Preferably, it is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy-C1-C6 alkyl, di(C1-C6 alkoxy)C1-C6 alkyl, C1-C6 alkylcarbonyl-C1-C6 alkyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C3-C6 cycloalkyl-C1-C6 alkyl;

[0119] Particularly preferred are hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or C1-C6 haloalkyl;

[0120] Particularly preferred are hydrogen, C1-C6 alkyl or C3-C6 alkynyl;

[0121] More preferably, it is hydrogen, CH3, C2H5 or CH2C≡CH.

[0122] Also preferred are pyridyl ethers of formula (I) wherein R 7 is H or C1-C6 alkyl; more preferably H; still more preferably C1-C6 alkyl.

[0123] Also preferred are pyridyl ethers of formula (I) wherein R 8 is H or C1-C6 alkyl; more preferably H; still more preferably C1-C6 alkyl.

[0124] Also preferred are pyridyl ethers of formula (I) wherein R 9 It is phenyl or C1-C4 alkyl; particularly preferably phenyl or CH3; further particularly preferably phenyl; further particularly preferably C1-C4 alkyl.

[0125] Also preferred are pyridyl ethers of formula (I) wherein R 10 It is phenyl or C1-C4 alkyl; particularly preferably phenyl or CH3; further particularly preferably phenyl; further particularly preferably C1-C4 alkyl.

[0126] Also preferred are pyridyl ethers of formula (I) wherein R 11 It is halogen or C1-C6 alkyl; particularly preferably F, Cl or CH3; also particularly preferably halogen; particularly preferably F or Cl; also particularly preferably C1-C6 alkyl; particularly preferably CH3.

[0127] Pyridyl ethers of the formula (I) are also preferred, in which n is 1 or 2; 2 is particularly preferred; 1 is also particularly preferred.

[0128] Pyridyl ethers of the formula (I) in which Q is O or S are also preferred; O is particularly preferred.

[0129] Pyridyl ethers of the formula (I) in which W is O, preferably S, are also preferred.

[0130] Pyridyl ethers of the formula (I) in which X is O, preferably S, are also preferred.

[0131] According to a preferred embodiment of the invention, preference is also given to those pyridyl ethers of the formula (I) in which the variables, independently of one another or in combination with one another, have the following meanings:

[0132] Y is preferably Y 2 , Y 13 , Y 20 , Y 31 , Y 37 , Y 38 , Y 39 , Y 42 , Y 48 , Y 55 , Y 65 , Y 66 , Y 67 , Y 68 or Y 76 ;

[0133] Y is particularly preferred 2 , Y 20 , Y 31 , Y 38 , Y 48 , Y 55 , Y 65 , Y 67 , Y 68 or Y 76 ;

[0134] Y is particularly preferred 2 , Y 20 , Y 38 , Y 55 , Y 65 , Y 66 , Y 67 or Y 76 ;

[0135] More preferably, Y 2 , Y 20 , Y 55 , Y 65 , Y 67 or Y 76 ;

[0136] Preferred Y is also preferably Y 2 , Y 13 , Y 20, Y 31 , Y 37 , Y 38 , Y 39 , Y 42 , Y 48 , Y 55 ,

[0137] Y 65 , Y 66 , Y 67 or Y 68 ;

[0138] Y is particularly preferred 2 , Y 20 , Y 31 , Y 38 , Y 48 , Y 55 , Y 65 , Y 67 or Y 68 ;

[0139] Y is particularly preferred 2 , Y 20 , Y 38 , Y 55 , Y 65 , Y 66 or Y 67 ;

[0140] More preferably, Y 2 , Y 20 , Y 55 , Y 65 or Y 67 ;

[0141] A 1 and A 2 Preferably oxygen; Also preferably sulfur;

[0142] A 3 Preferably it is oxygen, and more preferably it is sulfur;

[0143] A 4 Preferably oxygen, also preferably sulfur;

[0144] R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 Preferably H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl,

[0145] or

[0146] R12 and R 13 Together with the atoms to which they are attached, they form a 3-6 membered ring, which is saturated, partially unsaturated or aromatic, which in addition to carbon atoms may contain 1-4 nitrogen atoms, or 1 oxygen atom, or 1 sulfur atom, and which itself may be partially or completely halogenated and / or substituted by 1-3 C1-C6 alkyl groups;

[0147] Particularly preferred are H, C1-C6 alkyl, C1-C6 haloalkyl,

[0148] or

[0149] R 12 and R 13 Together with the atoms to which they are attached, they form a 6-membered ring, which is saturated,

[0150] Especially preferred are H, C1-C6 alkyl, C1-C6 haloalkyl;

[0151] More preferably H, CH3 or CF3;

[0152] Preferred R 12 , R 13 and R 14 Also preferably H, hydroxyl, C1-C6 alkyl or C1-C6 haloalkyl;

[0153] Particularly preferred are H, hydroxyl or C1-C6 haloalkyl;

[0154] Especially preferred are H, hydroxyl or CF3;

[0155] Preferred R 12 Also preferably a C1-C6 alkyl or a C1-C6 haloalkyl;

[0156] Particularly preferred are CH3 or CF3;

[0157] CF3 is particularly preferred;

[0158] Also preferably R 13 is H;

[0159] Preferred R 14 Also preferably H, hydroxyl, CH3 or CF3;

[0160] Particularly preferred is H or hydroxyl;

[0161] Particularly preferred is hydroxyl;

[0162] R 16 and R 17 Most preferably, it is C1-C6 haloalkyl;

[0163] R 18 Most preferably CH3;

[0164] R 19 , R 20 , R 21 , R 22 , R 23 and R 24 is hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl,

[0165] or

[0166] R 21 and R 22 Together with the atoms to which they are attached, they form a 5-6 membered ring, which is saturated, partially unsaturated or aromatic, which in addition to carbon atoms may contain 1 to 4 nitrogen atoms, or 1 or 2 oxygen atoms, or 1 or 2 sulfur atoms, and which itself may be partially or fully halogenated and / or substituted by one or more C1-C6 alkyl groups;

[0167] Particularly preferably, hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 haloalkoxy, or

[0168] R 21 and R 22 Together with the atoms to which they are attached, they form a 5-6 membered ring, which is saturated and which itself may be partially or fully halogenated and / or substituted with one or more C1-C6 alkyl groups;

[0169] Particularly preferred are C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 haloalkoxy,

[0170] or

[0171] R 21 and R 22 Together with the atoms to which they are attached, they form a 6-membered ring, which is saturated;

[0172] More preferably CH3, CF3, CF2H or OCF2H;

[0173] R 25 Preferably it is C1-C6 alkyl or C1-C6 haloalkyl;

[0174] R 26 and R 27 Preferably hydrogen, halogen or C1-C6 alkyl;

[0175] Particularly preferred is a C1-C6 alkyl group;

[0176] R 28 , R 29 and R30 Preferably hydrogen, halogen or C1-C6 alkyl;

[0177] More preferably, it is halogen or C1-C6 alkyl;

[0178] Most preferably, halogen;

[0179] Most preferably, it is a C1-C6 alkyl group;

[0180] Also most preferably is hydrogen;

[0181] R 31 Preferably C1-C6 alkyl;

[0182] R 32 , R 33 and R 34 Preferably, it is hydrogen, halogen, C1-C6 alkyl or C1-C6 haloalkyl;

[0183] Particularly preferred is C1-C6 haloalkyl;

[0184] R 35 and R 36 Preferably it is hydrogen, amino, C1-C6 alkyl or C1-C6 haloalkyl;

[0185] A C1-C6 alkyl group is particularly preferred.

[0186] Also preferred are pyridyl ethers of formula (I), wherein

[0187] Z is phenyl or pyridyl,

[0188] each of which is optionally substituted with 1-4 substituents selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0189] Preferably, phenyl,

[0190] which is optionally substituted with 1-4 substituents selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0191] Also preferably pyridyl,

[0192] It is optionally substituted with 1 to 4 substituents selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy.

[0193] Also preferred are pyridyl ethers of formula (I), wherein

[0194] Z is phenyl or pyridyl,

[0195] each of which is optionally substituted with 1-4 substituents selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0196] Preferably it is phenyl or pyridyl,

[0197] each of which is optionally substituted with 1 to 4 substituents selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;

[0198] Particularly preferably, it is phenyl or pyridyl,

[0199] Each of which is optionally substituted with 1 to 4 substituents selected from halogen or C1-C6 alkyl;

[0200] Particularly preferred are phenyl or pyridyl,

[0201] Each of which is optionally substituted with 1-4 substituents selected from F, Cl or CH3;

[0202] More preferably, it is phenyl or pyridyl,

[0203] Each of them has not been replaced.

[0204] Also preferred are pyridyl ethers of formula (I), wherein

[0205] Z is phenyl,

[0206] which is optionally substituted with 1-4 substituents selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0207] Preferably, phenyl,

[0208] which is optionally substituted with 1-4 substituents selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;

[0209] Particularly preferred is phenyl,

[0210] which is optionally substituted with 1 to 4 substituents selected from halogen or C1-C6 alkyl;

[0211] Particularly preferred is phenyl,

[0212] which is optionally substituted with 1-4 substituents selected from F, Cl or CH3;

[0213] More preferred is unsubstituted phenyl.

[0214] Also preferred are pyridyl ethers of formula (I), wherein

[0215] Z is pyridyl,

[0216] which is optionally substituted with 1-3 substituents selected from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0217] Preferably it is pyridyl,

[0218] which is optionally substituted with 1-3 substituents selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;

[0219] Particularly preferred is pyridyl,

[0220] which is optionally substituted with 1 to 3 substituents selected from halogen or C1-C6 alkyl;

[0221] Especially preferred is pyridyl,

[0222] It is optionally substituted with 1-3 substituents selected from F, Cl or CH3;

[0223] More preferably, it is unsubstituted.

[0224] Also preferred are pyridyl ethers of formula (I) wherein Z is selected from Z 1 -Z 29 :

[0225]

[0226]

[0227] in

[0228] * indicates the connection point between Z and X;

[0229] ** indicates the point of connection between Z and Q; and

[0230] R a , R b , R c , R d and R e are independently H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy;

[0231] Preferably H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;

[0232] Particularly preferred are H, halogen or C1-C6 alkyl;

[0233] Especially preferred are H, F, Cl or CH3;

[0234] More preferably H.

[0235] Also preferred are pyridyl ethers of formula (I) wherein Z is selected from Z as defined above 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 and Z 21 ; Particularly preferably selected from Z as defined above 1 , Z 2 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 and Z 21 ; Particularly preferably selected from Z as defined above 1 , Z 4 , Z 5 , Z 6 and Z 7 ; More preferably selected from Z as defined above 1 and Z 7 .

[0236] Also preferred are pyridyl ethers of formula (I), wherein

[0237] Z is selected from Z as defined above 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 ,

[0238] Z 12 , Z 13 and Z 21 ; where R a , R b , R c , R d and R e are independently H, halogen,

[0239] CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy;

[0240] Preferred are H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; particularly preferred are H, halogen or C1-C6 alkyl; particularly preferred are H, F, Cl or CH3;

[0241] More preferably H;

[0242] Particularly preferably, Z is selected from the group consisting of 1 , Z 2 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 and Z 21 , where R a , R b , R c , R d and R e are independently H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy; preferably H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;

[0243] Particularly preferred are H, halogen or C1-C6 alkyl; particularly preferred are H, F, Cl or CH3; more preferably H;

[0244] Particularly preferably, Z is selected from the group consisting of 1 , Z 4 , Z 5 , Z 6 and Z 7 , where R a , R b , R c , R d and R e are independently H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy; preferably H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; particularly preferably H, halogen or C1-C6 alkyl;

[0245] Especially preferred are H, F, Cl or CH3; more preferably H;

[0246] More preferably, Z is selected from the group consisting of1 and Z 7 , where R a , R b , R c , R d and R e are independently H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy;

[0247] Preferably H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;

[0248] Particularly preferred are H, halogen or C1-C6 alkyl; especially preferred are H, F, Cl or CH3; and more preferred is H.

[0249] Also preferred are pyridyl ethers of the formula (I) wherein R 1 H or F, and R 2 is F, Cl or CN.

[0250] Also preferred are pyridyl ethers of the formula (I) wherein R 3 is H, C1-C3 alkyl or C1-C3 alkoxy, and R 4 For H.

[0251] Also preferred are pyridyl ethers of formula (I), wherein

[0252] R 5 OR 6 NR 6 S(O)2R 7 or NR 6 S(O)2NR 7 R 8 ,in

[0253] R 6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy-C1-C6 alkyl, di(C1-C6 alkoxy)C1-C6 alkyl, C1-C6 alkylcarbonyl-C1-C6 alkyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C3-C6 cycloalkyl-C1-C6 alkyl; and R 7 , R 8 It is a C1-C6 alkyl group.

[0254] Pyridyl ethers of the formula (I) in which n is 1 are also preferred.

[0255] Pyridyl ethers of formula (I) wherein Q, W and X are O are also preferred.

[0256] Also preferred are pyridyl ethers of formula (I), wherein

[0257] R 1 is H or halogen;

[0258] R 2 is halogen or CN;

[0259] R 3 is H, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio;

[0260] R 4 is H;

[0261] R 5 OR 6 , SR 6 NR 7 R 8 NR 6 S(O)2R 7 or NR 6 S(O)2NR 7 R 8 ;in

[0262] R 6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C3-C6 haloalkenyl, C3-C6 haloalkynyl, C1-C6 cyanoalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkoxy-C1-C6 alkyl, di(C1-C6 alkoxy)C1-C6 alkyl, C1-C6 haloalkoxy-C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkyl, C3-C6 haloalkenyloxy-C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl, C1-C6 alkylsulfinyl -C1-C6 alkyl, C1-C6 alkylsulfonyl-C1-C6 alkyl, C1-C6 alkylcarbonyl-C1-C6 alkyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl, C1-C6 haloalkoxycarbonyl-C1-C6 alkyl, C3-C6 alkenyloxycarbonyl-C1-C6 alkyl, amino, C1-C6 alkylamino, di-C1-C6 alkylamino, C1-C6 alkylcarbonylamino, amino-C1-C6 alkyl, C1-C6 alkylamino-C1-C6 alkyl, di-C1-C6 alkylamino-C1-C6 alkyl, aminocarbonyl-C1-C6 alkyl, C1-C6 alkylaminocarbonyl-C1-C6 alkyl, di-C1-C6 alkylaminocarbonyl-C1-C6 alkyl,

[0263] -N=CR9 R 10 ,

[0264] Where R 9 and R 10 are independently H, C1-C4 alkyl or phenyl;

[0265] C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 heterocyclyl, phenyl, phenyl-C1-C4 alkyl or 5- or 6-membered heteroaryl,

[0266] wherein the cycloalkyl, heterocyclyl, phenyl or heteroaryl rings can each be substituted by 1 to 4 groups selected from R 11 or a 3-7 membered carbon ring substituent,

[0267] The carbocyclic ring optionally has, in addition to the carbon atoms, 1 or 2 selected from -N(R 11 )-、-N=N-、-C(=O)-、

[0268] -O- and -S- ring members, and

[0269] The carbon ring is optionally substituted by 1 to 4 groups selected from R 11 Substituents are substituted;

[0270] R 7 is a C1-C6 alkyl group;

[0271] R 8 is H or C1-C6 alkyl;

[0272] R 9 is phenyl or CH3;

[0273] R 10 is phenyl or CH3;

[0274] R 11 is halogen or C1-C6 alkyl;

[0275] n is 1 or 2;

[0276] Q is O, S, SO, SO2, NH or (C1-C3 alkyl)N;

[0277] W is O;

[0278] X is O;

[0279] Z is Z as defined above 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z9 , Z 10 , Z 11 , Z 12 , Z 13 and Z 21 ,in

[0280] R a , R b , R c , R d and R e are independently H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy;

[0281] Particularly preferred are pyridyl ethers of formula (I), wherein

[0282] R 1 is H or halogen;

[0283] R 2 is halogen or CN;

[0284] R 3 is H, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 alkoxy;

[0285] R 4 is H;

[0286] R 5 OR 6 NR 7 R 8 NR 6 S(O)2R 7 or NR 6 S(O)2NR 7 R 8 ;in

[0287] R 6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy-C1-C6 alkyl, di(C1-C6 alkoxy)C1-C6 alkyl, C1-C6 alkylcarbonyl-C1-C6 alkyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C3-C6 cycloalkyl-C1-C6 alkyl;

[0288] R 7 is a C1-C6 alkyl group;

[0289] R 8 is H or C1-C6 alkyl;

[0290] n is 1;

[0291] Q is O, S, SO, SO2, NH or (C1-C3 alkyl)N;

[0292] W is O;

[0293] X is O;

[0294] Z is selected from Z as defined above 1 , Z 2 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 and Z 21 , where R a , R b , R c , R d and R e are independently H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy;

[0295] Especially preferred are pyridyl ethers of formula (I), wherein

[0296] R 1 is H, F or Cl;

[0297] R 2 is F, Cl or CN;

[0298] R 3 is H, C1-C3 alkyl or C1-C3 alkoxy;

[0299] R 4 is H;

[0300] R 5 OR 6 or NR 6 S(O)2R 7 ,in

[0301] R 6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl or C1-C6 haloalkyl, and

[0302] R 7 is a C1-C6 alkyl group;

[0303] n is 1;

[0304] Q is O or S;

[0305] W is O;

[0306] X is O;

[0307] Z is selected from Z as defined above 1 , Z 4 , Z 5 , Z 6 and Z 7 , where R a , R b , R c , R d and R e

[0308] are independently H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy;

[0309] More preferably, the pyridyl ethers are of the following formula (I), wherein

[0310] R 1 is H, F or Cl;

[0311] R 2 is F, Cl or CN;

[0312] R 3 is H, CH3 or OCH3;

[0313] R 4 is H;

[0314] R 5 OR 6 or NR 6 S(O)2R 7 ;in

[0315] R 6 is hydrogen, C1-C6 alkyl or C3-C6 alkynyl, and

[0316] R 7 is a C1-C6 alkyl group;

[0317] n is 1;

[0318] Q is O;

[0319] W is O;

[0320] X is O;

[0321] Z is selected from Z as defined above 1 and Z 7 , where R a , R b , R c , R d and R eIndependently of each other are H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy.

[0322] Also preferred are pyridyl ethers of formula (I), wherein

[0323] R 1 is H, F or Cl;

[0324] R 2 is F, Cl or CN;

[0325] R 3 is H, CH3 or OCH3;

[0326] R 4 is H;

[0327] R 5 OR 6 , SR 6 NR 7 R 8 NR 6 OR 6 NR 6 S(O)2R 7 or NR 6 S(O)2NR 7 R 8 ,in

[0328] R 6is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C3-C6 haloalkenyl, C3-C6 haloalkynyl, C1-C6 cyanoalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkoxy-C1-C6 alkyl, di(C1-C6 alkoxy)C1-C6 alkyl, C1-C6 haloalkoxy-C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkyl, C3-C6 haloalkenyloxy-C1-C6 alkyl, C3-C6 alkenyloxy-C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl, C1-C6 alkylsulfinyl-C1-C6 alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-haloalkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, amino, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylcarbonylamino, amino-C1-C6-alkyl, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, aminocarbonyl-C1-C6-alkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkyl, di-C1-C6-alkylaminocarbonyl-C1-C6-alkyl,

[0329] -N=CR 9 R 10 , where R 9 and R 10 are independently H, C1-C4 alkyl or phenyl;

[0330] C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 heterocyclic group, C3-C6 heterocyclic group

[0331] -C1-C6 alkyl, phenyl, phenyl-C1-C4 alkyl or 5- or 6-membered heteroaryl,

[0332] wherein the cycloalkyl, heterocyclyl, phenyl or heteroaryl rings can each be substituted by 1 to 4 groups selected from R 14 or

[0333] Substitution of a 3-7 membered carbon ring,

[0334] The carbocyclic ring optionally has, in addition to the carbon atoms, 1 or 2 selected from -N(R 9 )-、-N=N-、-C(=O)-、

[0335] -O- and -S- ring members, and

[0336] The carbon ring is optionally substituted by 1 to 4 groups selected from R 11 Substituents are substituted;

[0337] Where R 11 is halogen, NO2, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 alkoxycarbonyl;

[0338] R 7 , R 8 Independently of each other, R 9 , or together form a 3-7 member carbon ring,

[0339] The carbocyclic ring optionally has, in addition to the carbon atoms, 1 or 2 selected from -N(R 10 )-、-N=N-、-C(=O)-、

[0340] -O- and -S- ring members, and

[0341] The carbon ring is optionally substituted by 1 to 4 groups selected from R 11 Substituents are substituted;

[0342] n is 1;

[0343] Q is O;

[0344] W is O;

[0345] X is O;

[0346] Z is selected from Z as defined above 1 and Z 7 , where R a , R b , R c , R d and R e Independently of each other are H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy.

[0347] Particularly preferred are pyridyl ethers of the following formula (Ia) (corresponding to formula (I), wherein Y is Y 2 , where R 19 Br, R 20 For CF3 and R 21 is CH3, and R 4 is H, n is 1, Q, W and X are O and Z is Z-1 as defined, wherein R a , R b , R c , R d and R e For H):

[0348]

[0349] The variable R 1 , R 2 , R 3 and R 5 has the meanings as defined above, especially the preferred meanings.

[0350] Particularly preferred are compounds of formulae Ia1 to Ia36 of Table A, wherein the variable R 1 , R 2 , R 3 and R 5 The definitions of are of particular importance for the compounds according to the invention not only in combination with one another but also individually in each case:

[0351] Table A

[0352]

[0353]

[0354] Pyridyl ethers of formula (Ib) are also preferred, and pyridyl ethers of formula (Ib1) to (Ib36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 2 , where R 28 Cl, R 23 is OCHF2, and R 24 For CH3:

[0355]

[0356] Pyridyl ethers of formula (Ic) are also preferred, and pyridyl ethers of formula (Ic1) to (Ic36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 13 , where A 1 and A 2 For O, R 19 is H, and R 21 and R 22 Together they form –(CH2-CHF-CH2)–:

[0357]

[0358] Pyridyl ethers of formula (Id) are also preferred, and pyridyl ethers of formula (Id1) to (Id36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 13 , where A 1 and A 2 For O, R19 is H, and R 21 and R 22 Together they form –(CH2-CHF-CH2)- in the form of the (6S, 7aR) stereoisomer:

[0359]

[0360] Pyridyl ethers of formula (Ie) are also preferred, and pyridyl ethers of formula (Ie1) to (Ie36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 20 , A 1 For O, R 21 For CHF2, R 22 For CH3:

[0361]

[0362] Pyridyl ethers of formula (If) are also preferred, and pyridyl ethers of formula (If1) to (If36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 20 , A 1 is O, and R 21 and R 22 Together they form –(CH2)4–:

[0363]

[0364] Pyridyl ethers of formula (Ig) are also preferred, and pyridyl ethers of formula (Ig1) to (Ig36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 31 , where A 1 and A 2 is O, and R 26 and R 27 For CH3:

[0365]

[0366] Pyridyl ethers of formula (Ih) are also preferred, and pyridyl ethers of formula (Ih1) to (Ih36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 37 , where A 1 for O,A 4 is S, and R 21 and R 22 Together they form –(CH2)4–:

[0367]

[0368] Pyridyl ethers of formula (Ii) are also preferred, and pyridyl ethers of formula (Ii1) to (Ii36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 38 , where A 1 is O, and R 28 For C(CH3)3:

[0369]

[0370] Pyridyl ethers of formula (Ik) are also preferred, and pyridyl ethers of formula (Ik1) to (Ik36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 39 , where A 1 is S, and R 21 and R 22 Together they form –(CH2-C(CH3)2-CH2)–:

[0371]

[0372] Pyridyl ethers of formula (Il) are also preferred, and pyridyl ethers of formula (Il1) to (Il36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 42 , where R 30 Cl, R 14 For H, R 16 is CF3, and R 15 For H:

[0373]

[0374] Pyridyl ethers of formula (Im) are also preferred, and pyridyl ethers of formula (Im1) to (Im36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 48 , where A 1 For O, R 32 is CF3, and R 35 For CH3:

[0375]

[0376] Pyridyl ethers of formula (In) are also preferred, and pyridyl ethers of formula (In1) to (In36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 55 , where A 1 For O, R 28 For H, R 17 is CF3, and R 18 For CH3:

[0377]

[0378] Pyridyl ethers of formula (Io) are also preferred, and pyridyl ethers of formula (Io1) to (Io36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 65 , where A 1 For O, R 12 For H, R 13 is CF3, and R 35 For CH3:

[0379]

[0380] Pyridyl ethers of formula (Ip) are also preferred, and pyridyl ethers of formula (Ip1) to (Ip36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 66 , where A 1 For O, R 12 For CF3, R 13 is H, and R 35 For CH3:

[0381]

[0382] Pyridyl ethers of formula (Iq) are also preferred, and pyridyl ethers of formula (Iq1) to (Iq36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 67 , where A 1 and A 2 for O,A 3 For S, R 35 and R 36 For CH3:

[0383]

[0384] Pyridyl ethers of formula (Ir) are also preferred, and pyridyl ethers of formula (Ir1) to (Ir36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 68 , where A 1 and A 2 For O, R 12 and R 13 Together they form –(CH2)4-:

[0385]

[0386] Pyridyl ethers of formula (Is) are also preferred, particularly pyridyl ethers of formula (Is1) to (Is36), which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Z is Z-7 as defined, wherein R a , R b and R c For H:

[0387]

[0388] Pyridyl ethers of formula (It) are also preferred, and pyridyl ethers of formula (It1) to (It36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 2 , where R 28 Cl, R 23 For OCHF2 and R 24 is CH3, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0389]

[0390] Pyridyl ethers of formula (Iu) are also preferred, and pyridyl ethers of formula (Iu1) to (Iu36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 13 , where A 1 and A 2 For O, R 19 is H, and R 21 and R 22 together to form -(CH2-CHF-CH2)-, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0391]

[0392] Pyridyl ethers of formula (Iv) are also preferred, and pyridyl ethers of formula (Iv1) to (Iv36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 13 , where A 1 and A 2 For O, R 19 is H, and R 21 and R 22 Together they form –(CH2-CHF-CH2)– in the form of the (6S, 7aR) stereoisomer, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0393]

[0394] Pyridyl ethers of formula (Iw) are also preferred, and pyridyl ethers of formula (Iw1) to (Iw36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 20 , A 1 For O, R 21 For CHF2, R 22 is CH3, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0395]

[0396] Pyridyl ethers of formula (Ix) are also preferred, and pyridyl ethers of formula (Ix1) to (Ix36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 20 , A 1 is O, and R 21 and R 22 together to form -(CH2)4-, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0397]

[0398] Pyridyl ethers of formula (Iy) are also preferred, and pyridyl ethers of formula (Iy1) to (Iy36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 31 , where A 1 and A 2 is O, and R 26 and R 27 is CH3, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0399]

[0400] Pyridyl ethers of formula (Iz) are also preferred, and pyridyl ethers of formula (Iz1) to (Iz36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 37 , where A 1 for O,A 4 is S, and R 21 and R 22 together to form -(CH2)4-, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0401]

[0402] Pyridyl ethers of formula (I.aa) are also preferred, and pyridyl ethers of formula (I.aa.1) to (I.aa.36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 38 , where A 1 is O, and R 28 is C(CH3)3, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0403]

[0404] Pyridyl ethers of formula (I.ab) are also preferred, and pyridyl ethers of formula (I.ab.1) to (I.ab.36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 39 , where A 1 is S, and R 21 and R 22together to form -(CH2-C(CH3)2-CH2)-, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0405]

[0406] Pyridyl ethers of formula (I.ac) are also preferred, and pyridyl ethers of formula (I.ac.1) to (I.ac.36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 42 , where R 30 Cl, R 14 For H, R 16 is CF3, and R 15 is H, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0407]

[0408] Pyridyl ethers of formula (I.ad) are also preferred, and pyridyl ethers of formula (I.ad.1) to (I.ad.36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 48 , where A 1 For O, R 32 is CF3, and R 35 is CH3, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0409]

[0410] Pyridyl ethers of formula (I.ae) are also preferred, and pyridyl ethers of formula (I.ae.1) to (I.ae.36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 55 , where A 1 For O, R 28 For H, R 17 is CF3, and R 18 is CH3, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0411]

[0412] Pyridyl ethers of formula (I.af) are also preferred, particularly pyridyl ethers of formula (I.af.1) to (I.af.36) which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 65 , where A 1 For O, R 12 For H, R 13 is CF3, and R 35 is CH3, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0413]

[0414] Pyridyl ethers of formula (I.ag) are also preferred, and pyridyl ethers of formula (I.ag.1) to (I.ag.36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 66 , where A 1 For O, R 12 For CF3, R 13 is H, and R 35 is CH3, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0415]

[0416] Pyridyl ethers of formula (I.ah) are also preferred, and pyridyl ethers of formula (I.ah.1) to (I.ah.36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 67 , where A 1 and A 2 for O,A 3 For S, R 35 and R 36 is CH3, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0417]

[0418] Pyridyl ethers of formula (I.ai) are also preferred, and pyridyl ethers of formula (I.ai.1) to (I.ai.36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 68 , where A 1 and A 2 For O, R 12 and R 13 together to form -(CH2)4-, and Z is Z-7 as defined, wherein R a , R b and R c For H:

[0419]

[0420] Pyridyl ethers of formula (I.ak) are also preferred, particularly pyridyl ethers of formula (I.ak.1) to (I.ak.36) which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 76 , where A 1 and A 2 For O, R 12 For CF3, R 13 and R 15 For H, R 14 is OH, and R 22 For H:

[0421]

[0422] Pyridyl ethers of formula (I.al) are also preferred, and pyridyl ethers of formula (I.al.1) to (I.al.36) are particularly preferred, which differ from the corresponding pyridyl ethers of formula (Ia1) to (Ia36) only in that Y is Y 76 , where A 1 and A 2 For O, R 12 For CF3, R 13 and R 15 For H, R 14 is OH, and R 22 For H:

[0423]

[0424] The pyridyl ethers of formula (I) of the present invention can be prepared by standard methods of organic chemistry, for example by the following methods AE:

[0425] Method A)

[0426] Pyridyl ethers of formula (I) can be prepared by reacting a pyridine of formula (II) with a compound of formula (III) in the presence of a base:

[0427]

[0428] In the pyridine of formula (II), L 1 It is a leaving group, such as halogen, C1-C6 alkylsulfonate or arylsulfonate; preferably F, Cl, C1-C6 alkylsulfonate or arylsulfonate; especially preferably F, Cl, OSO2CH3 (mesylate) or OSO2C6H4CH3 (toluenesulfonate); more preferably F or Cl.

[0429] The compounds of formula (III) can also be used in the form of their salts, in particular the sodium and potassium salts, without necessarily requiring the presence of a base.

[0430] The reaction of pyridine (II) with compound (III) in the presence of a base is usually carried out at a temperature from 0°C to the boiling point of the reaction mixture, preferably from 40 to 100°C.

[0431] The reaction can in principle be carried out in bulk. However, preference is given to reacting the pyridine of the formula (II) with the compound of the formula (III) in an organic solvent.

[0432] Suitable in principle are all solvents which are able to dissolve the pyridine of the formula (II) and the compound of the formula (III) at least partially, preferably completely, under the reaction conditions.

[0433] Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8 paraffins; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-xylene, m-xylene and p-xylene; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), ... alkane, anisole and tetrahydrofuran (THF); esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone, diethyl ketone, tert-butyl methyl ketone, cyclohexanone; and dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidone (NMP).

[0434] Preferred solvents are ethers, nitriles, ketones and dipolar aprotic solvents as described above.

[0435] More preferred solvents are ethers and dipolar aprotic solvents as described above.

[0436] It is also possible to use mixtures of the solvents mentioned.

[0437] Examples of suitable bases include metal-containing bases and nitrogen-containing bases.

[0438] Examples of suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal oxides and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal hydroxides and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; organometallic compounds, preferably alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methyl chloride Magnesium and alkali metal and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-amylate and dimethoxymagnesium; alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate and calcium carbonate, and alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates such as potassium phosphate, calcium phosphate; in addition there are organic bases, such as tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine and 4-dimethylaminopyridine and also bicyclic amines.

[0439] Examples of suitable nitrogen-containing bases are C1-C6-alkylamines, preferably trialkylamines, such as triethylamine, trimethylamine, N-ethyldiisopropylamine; ammonia, pyridine, lutidine, collidine, 4-dimethylaminopyridine (DMAP), imidazole, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN).

[0440] Preferred are basic alkali metal and alkaline earth metal hydrides, alkali metal and alkaline earth metal carbonates and alkali metal hydrogencarbonates; alkali metal and alkaline earth metal phosphates; organometallic compounds, alkylmagnesium halides and alkali metal and alkaline earth metal alkoxides; furthermore organic bases, such as tertiary amines, pyridine, substituted pyridines and also bicyclic amines.

[0441] Particularly preferred bases are alkali metal and alkaline earth metal carbonates, organometallic compounds, alkylmagnesium halides and alkali metal and alkaline earth metal alkoxides; furthermore organic bases, such as tertiary amines, pyridine, substituted pyridines and also bicyclic amines.

[0442] The term base as used herein also includes mixtures of two or more, preferably two, of the abovementioned compounds. Particular preference is given to using one base.

[0443] The base is usually used in excess, more preferably in 1 to 3 molar equivalents based on the pyridine of the formula (II), and they may also serve as a solvent.

[0444] For the reaction, the pyridine of formula (II), the compound of formula (III) and the base themselves can be contacted in any manner.

[0445] Thus, the reaction partner and the base can be introduced into the reaction vessel separately, simultaneously or sequentially and reacted.

[0446] The reactants are generally used in equimolar amounts. It may be advantageous to use one of the reactants in excess, for example in order to complete the reaction of the other reactant.

[0447] The reaction can be carried out at atmospheric pressure, reduced pressure or elevated pressure, if appropriate under inert gas, continuously or batchwise.

[0448] The completion of the reaction can be easily determined by the skilled worker by means of conventional methods.

[0449] The reaction mixture is worked up in a customary manner, for example by filtering, mixing with water, separating the phases and, if appropriate, purifying the crude product by chromatography.

[0450] Some of the intermediates and final products are obtained in the form of viscous oils which can be purified or freed from volatile components under reduced pressure and mildly elevated temperatures.

[0451] If the intermediates and end products are obtained as solids, they can also be purified by recrystallization or digestion.

[0452] Method B)

[0453] Alternatively, it can also be prepared by reacting a compound of the formula (IV) with an alkylating agent of the formula (V) in the presence of a base in analogy to known methods (eg WO 11 / 137088):

[0454]

[0455] In the alkylating agent of formula (V), L 2 is a leaving group, such as halogen, C1-C6 alkylsulfonate or arylsulfonate; preferably Cl, Br, I, C1-C6 alkylsulfonate or arylsulfonate; particularly preferably Cl, Br or I; more preferably Cl or Br.

[0456] The reaction of the compound of formula (IV) with the alkylating agent of formula (V) in the presence of a base is usually carried out at 0°C to the boiling point of the reaction mixture, preferably 20-100°C.

[0457] The reaction can in principle be carried out in bulk. However, preference is given to reacting the compound of the formula (IV) with the alkylating agent of the formula (V) in an organic solvent.

[0458] Suitable in principle are all solvents which are able to dissolve the compound of the formula (IV) and the alkylating agent of the formula (V) at least partially, preferably completely, under the reaction conditions.

[0459] Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8 paraffins; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-xylene, m-xylene and p-xylene; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), ... alkane, anisole and tetrahydrofuran (THF); esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone, diethyl ketone, tert-butyl methyl ketone, cyclohexanone; and dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidone (NMP).

[0460] Preferred solvents are ethers, nitriles, ketones and dipolar aprotic solvents as described above.

[0461] More preferred solvents are ethers and dipolar aprotic solvents as described above.

[0462] It is also possible to use mixtures of the solvents mentioned.

[0463] Examples of suitable bases include metal-containing bases and nitrogen-containing bases.

[0464] Examples of suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; alkali metal and alkaline earth metal oxides and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, cesium carbonate and Calcium carbonate, and alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates such as potassium phosphate, calcium phosphate; metal organic compounds, preferably alkali metal alkyls such as methyl lithium, butyl lithium and phenyl lithium, alkyl magnesium halides such as methyl magnesium chloride and alkali metal and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-amylate and dimethoxymagnesium; in addition there are organic bases, such as tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine and 4-dimethylaminopyridine and also bicyclic amines.

[0465] Examples of suitable nitrogen-containing bases are C1-C6-alkylamines, preferably trialkylamines, such as triethylamine, trimethylamine, N-ethyldiisopropylamine; ammonia, pyridine, lutidine, collidine, 4-dimethylaminopyridine (DMAP), imidazole, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN).

[0466] Preferred are basic alkali metal and alkaline earth metal hydrides, alkali metal and alkaline earth metal carbonates and alkali metal hydrogencarbonates; alkali metal and alkaline earth metal phosphates; organometallic compounds, alkylmagnesium halides and alkali metal and alkaline earth metal alkoxides; furthermore organic bases, such as tertiary amines, pyridine, substituted pyridines and also bicyclic amines.

[0467] Particularly preferred bases are alkali metal and alkaline earth metal carbonates, organometallic compounds, alkylmagnesium halides and alkali metal and alkaline earth metal alkoxides; furthermore organic bases, such as tertiary amines, pyridine, substituted pyridines and also bicyclic amines.

[0468] The term base as used herein also includes mixtures of two or more, preferably two, of the abovementioned compounds. Particular preference is given to using one base.

[0469] The base is usually used in an equimolar amount or in excess, more preferably in 1 to 20 molar equivalents based on the compound of formula (IV), and they may also serve as a solvent.

[0470] Preferably the base is used in 1 to 5 molar equivalents, very preferably 1 to 3 molar equivalents, more preferably 1 to 2 molar equivalents, based on the compound of the formula (IV).

[0471] It may be advantageous to stagger the addition of the base over a certain period of time.

[0472] The reactants are generally used in equimolar amounts. It may be advantageous to use one of the reactants in excess, for example in order to complete the reaction of the other reactant.

[0473] For the reaction, compound (IV), the alkylating agent of formula (V) and the base themselves can be contacted in any manner.

[0474] The reaction can be carried out at atmospheric pressure, reduced pressure or elevated pressure, if appropriate under inert gas, continuously or batchwise.

[0475] The completion of the reaction can be easily determined by the skilled worker by means of conventional methods.

[0476] The reaction mixture is worked up in a customary manner, for example by filtering, mixing with water, separating the phases and, if appropriate, purifying the crude product by chromatography.

[0477] Some of the intermediates and final products are obtained in the form of viscous oils which can be purified or freed from volatile components under reduced pressure and mildly elevated temperatures.

[0478] If the intermediates and end products are obtained as solids, they can also be purified by recrystallization or digestion.

[0479] As an alternative, pyridyl ethers of the formula (I), in which Y is a heterocycle which is bonded to the pyridine ring via the N-atom, can also be prepared from amino compounds of the formula (VI) in analogy to known methods:

[0480]

[0481] The process for converting compound (VI) into the pyridyl ether of formula (I) depends on the nature of the group Y.

[0482] These methods are described in particular as follows: Chemical Biology & Drug Design 2014, 84(4), 431 - 442 (Y8, Y9), Bioorganic & Medicinal Chemistry 2010, 18(22), 7948 - 7956 (Y10), JP01139580 (Y11), EP 1 157 991 (Y12), EP 311135 (Y13, Y17, Y20, Y38, Y39), DE 39 22 107 (Y14, Y31), JP 11292720 (Y15), US 4,670,043 (Y16), EP 334 055 (Y17, Y20, Y38), EP 75267 (Y18), EP 863 142 (Y19), EP 334055 (Y17, Y20, Y38), WO96 / 18618 (Y21), EP 282 303 (Y22), EP 305 923 (Y23), US 6,333,296 (Y24), Bioorganic & Medicinal Chemistry Letters 2010, 20(5), 1510 - 1515 (Y25, Y26), WO 2008 / 011072 (Y30), DE 39 22 107 (Y14, Y31), JP 07304759 (Y32), JP 06016664 (Y33), WO 2008 / 030902 (Y34), EP 683 160 (Y35), US5,726,126 (Y36), WO 96 / 02523 (Y37), WO 92 / 21684 (Y37), EP 334 055 (Y17, Y20, Y38), WO93 / 03043 (Y39, 62), EP 454 444 (Y50), CN 1687061 (Y51), EP 1 095 935 (Y52), EP 985 670 (Y53), J.Chem.Soc., Perkin Trans.1: Organic and Bio-Organic Chemistry 1993, (6), 731-5(Y54), WO 97 / 07104(Y55), WO 2010 / 100189(Y56), WO 99 / 11634(Y57), WO 86 / 00072(Y58), WO 2012 / 002096(Y59), EP 640 600(Y60, Y67), Zeitschrift für Chemie1986, 26(4), 134–136(Y61), EP 371 240(Y63, Y64), WO 98 / 41093(Y66), WO 10 / 145992(Y67),WO04 / 087694(Y68),WO 2000 / 013508(Y69), CN 1355164(Y70). .

[0483] Method D)

[0484] As an alternative, pyridyl ethers of formula (I), in which Y is a heterocycle which is bonded to the pyridine ring via a C-atom, can also be prepared by cross-coupling of compounds of formula (VII) with compounds of formula (VIII) in the presence of a transition metal catalyst in analogy to known methods (e.g. WO 95 / 22547 (Y 2 ), WO 98 / 07720(Y 42 ), WO 02 / 042275(Y 42 ), JP2009137851(Y 45 ) and WO 17 / 036266(Y 65 ):

[0485]

[0486] In the compound of formula (VII), L 3 is a leaving group, such as halogen or OSO2CF3 (trifluoromethanesulfonate); particularly preferably I, Br, Cl or OSO2CF3; more preferably I or Br.

[0487] In the compound of formula (VIII), M 1 is boric acid, alkyl borate, Sn-tri(C1-C4 alkyl); B(OH)2, B(O(C1-C 10 alkyl))2 or Sn-tri(C1-C4 alkyl); more preferably BO2C2(CH3)4 (="B-pin") or Sn-tri(C1-C4 alkyl).

[0488] The reaction is usually carried out at 0°C to the boiling point of the reaction mixture, preferably 15-110°C, particularly 40-100°C, in an inert organic solvent in the presence of a base and a catalyst.

[0489] The reaction can in principle be carried out in bulk. However, preference is given to reacting the compound of the formula (VII) with the compound of the formula (VIII) in an organic solvent in the presence or absence of water as a cosolvent.

[0490] Suitable solvents are those which are able to at least partially, preferably completely, dissolve the compound of formula (VII) and the compound of formula (VIII) under the reaction conditions.

[0491] Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-xylene, m-xylene and p-xylene; ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), ... dipolar aprotic solvents such as sulfolane, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidone (NMP).

[0492] Preferred solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), diisopropyl ether, and dipolar aprotic solvents such as sulfolane, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidone (NMP). More preferred solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dimethicone, ... The solvents mentioned are oxane, anisole and tetrahydrofuran (THF). It is also possible to use mixtures of the solvents mentioned.

[0493] Examples of suitable metal-containing bases are inorganic compounds, including metal-containing bases, such as alkali metal and alkaline earth metal hydroxides and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and Al(OH)3; alkali metal and alkaline earth metal oxides and other metal oxides, such as Li2O, Na2O, K2O, MgO and CaO, Fe2O3, Ag2O; alkali metal and alkaline earth metal carbonates such as Li2CO3, Na2CO3, K2CO3, Cs2CO3, MgCO3 and CaCO3, and alkali metal bicarbonates such as LiHCO3, NaHCO3, KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(PO4)2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.

[0494] Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and Al(OH)3; and alkali metal or alkaline earth metal carbonates such as Li2CO3, Na2CO3, K2CO3, Cs2CO3, MgCO3 and CaCO3, and alkali metal and alkaline earth metal phosphates such as K3PO4; alkali metal and alkaline earth metal acetates such as sodium acetate. Particularly preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and Al(OH)3, and alkaline earth metal phosphates such as K3PO4.

[0495] The term base as used herein also includes mixtures of two or more, preferably two, of the abovementioned compounds. Particular preference is given to using one base.

[0496] Preferably, the base is used in 1 to 10 equivalents, more preferably 1.0 to 5.0 equivalents, most preferably 1.2 to 2.5 equivalents, based on the compound of formula (VII).

[0497] It may be advantageous to stagger the addition of the base over a certain period of time.

[0498] The reaction of the compound of formula (VII) with the compound of formula (VIII) is carried out in the presence of a catalyst. Examples of suitable catalysts include, for example, palladium-based catalysts, such as palladium acetate (II), tetrakis (triphenylphosphine) palladium (0), bis (triphenylphosphine) palladium chloride (II) or (1,1-bis (diphenylphosphino) ferrocene) dichloropalladium (II), and optionally suitable additives such as phosphines, such as P (o-tolyl) 3, triphenylphosphine or BINAP (2,2'-bis (diphenylphosphino) -1,1'-binaphthyl).

[0499] The amount of the catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the compound of the formula (VII).

[0500] Method E)

[0501] As an alternative, depending on the nature of the group Y, the pyridyl ethers of the formula (I) can also be prepared by nucleophilic addition of compounds of the formula (IX) onto compounds of the formula (VII):

[0502]

[0503] In the compound of formula (VII), L 3 is a leaving group, such as halogen or OSO2CF3; particularly preferably F, Cl or OSO2CF3; more preferably F or Cl.

[0504] In the compound of formula (IX), M 2 It is a magnesium halide, a zinc halide, Li or Cu; magnesium halide or Li is particularly preferred.

[0505] The reaction is usually carried out in an inert organic solvent at a temperature from -78°C to the boiling point of the reaction mixture, preferably from 20 to 40°C.

[0506] The reaction can in principle be carried out in bulk. However, preference is given to reacting the compound of the formula (VII) with the compound of the formula (IX) in an organic solvent.

[0507] Suitable solvents are those which are able to at least partially, preferably completely, dissolve the compound of formula (VII) and the compound of formula (IX) under the reaction conditions.

[0508] Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-xylene, m-xylene and p-xylene; ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), ... dipolar aprotic solvents such as sulfolane, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidone (NMP).

[0509] Preferred solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), diisopropyl ether, Alkane, anisole and tetrahydrofuran (THF); and dipolar aprotic solvents such as sulfolane, N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N, N'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidone (NMP). More preferred solvents are ethers such as ether, diisopropyl ether, N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N, N'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidone (NMP). Mixtures of the solvents can also be used.

[0510] Method F)

[0511] Alternatively, pyridyl ethers of formula (I) wherein Y is Y 76 , where A 1 For O, R 14 is OH, and R 22 is H, and can also be prepared by reacting a compound of formula (XVIII) with an isocyanate salt (XXII) in the presence of an acid (e.g. EP 1 095935):

[0512]

[0513] In method F, preferably the variables have the following meanings: A 1 and A 2 O; R 12 For CF3, R 13 and R 22 For H,

[0514] Therefore, preferably, Y is Y 76 , A 1 and A 2 For O, R 12 For CF3, R 13 and R 15 For H, R 14 OH and R 22 The pyridyl ethers of formula (I) wherein A is H may be 2 For O, R 12 For CF3, R 13 and R 15 The compound of formula (XVIII) is prepared by reacting a compound of formula (XVIII) with an isocyanate (XXII) in the presence of an acid (eg EP 1 095 935):

[0515]

[0516] The reaction of the compound represented by the formula (XVIII) with the isocyanate salt (XXII) is usually carried out at a temperature from -20°C to the boiling point of the reaction mixture, preferably from 10 to 100°C, in the presence of an acid.

[0517] Suitable isocyanate salts (XXII) are generally salts of those cations which do not adversely affect the reaction.

[0518] Preferred cations are ions of alkali metals, preferably sodium and potassium, ions of alkaline earth metals, preferably calcium and magnesium, and ions of transition metals, preferably silver, copper and zinc, furthermore ammonium and substituted ammonium in which 1 to 4 hydrogen atoms are replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably tetraethylammonium and tetrabutylammonium.

[0519] The term "salt" as used herein also includes mixtures of two or more, preferably two, different salts as described above. Particular preference is given to using one salt.

[0520] Preference is given to alkali metal and alkaline earth metal isocyanates, particularly preferably KOCN.

[0521] In one embodiment of the process according to the invention, the isocyanate salt (XXII) is used in excess relative to the compound of the formula (XVIII).

[0522] In another embodiment of the process according to the invention, the isocyanate salt (XXII) and the compound of the formula (XVIII) are used in equimolar amounts.

[0523] Preferably, the molar ratio of the isocyanate salt (XXII) to the compound of formula (XVIII) is 1:1-3:1, preferably 1:1-2:1, and particularly preferably 2:1.

[0524] The reaction can in principle be carried out in bulk. However, preference is given to reacting the compound of the formula (XVIII) with the isocyanate salt (XXII) in an organic solvent.

[0525] Suitable in principle are all solvents which are able to dissolve the compound of the formula (XVIII) and the isocyanate salt (XXII) at least partially, preferably completely, under the reaction conditions.

[0526] Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8 paraffins; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-xylene, m-xylene and p-xylene; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), ... alkane, anisole and tetrahydrofuran (THF); esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone, diethyl ketone, tert-butyl methyl ketone, cyclohexanone; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol; and dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidone (NMP).

[0527] It is also possible to use mixtures of the solvents mentioned.

[0528] The reaction of the compound of formula (XVIII) with the isocyanate salt (XXII) is carried out in the presence of an acid.

[0529] As the acid and the acidic catalyst, there can be used inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and organic acids such as acetic acid, propionic acid, butyric acid, benzoic acid, toluenesulfonic acid, p-toluenesulfonic acid and methanesulfonic acid.

[0530] The acids are generally used in equimolar amounts, but they can also be used in excess or, if appropriate, as solvent.

[0531] The completion of the reaction can be easily determined by the skilled worker by means of conventional methods.

[0532] The reaction mixture is worked up in a customary manner, for example by mixing with water and optionally neutralizing, separating the phases and, if appropriate, purifying the crude product chromatographically.

[0533] Some of the intermediates and final products are obtained in the form of viscous oils which can be purified or freed from volatile components under reduced pressure and mildly elevated temperatures.

[0534] If the intermediates and end products are obtained as solids, they can also be purified by recrystallization or digestion.

[0535] By this process F, preferably pyridyl ethers (I.ak), particularly preferably pyridyl ethers of the formula (I.ak.1) to (I.ak.36) as defined above, can be obtained from compounds of the formula (XVIII.ak) in which R 1 , R 2 , R 3 and R 4 As defined herein, preferably as defined in Table A above:

[0536]

[0537] Preferably the isocyanate salt (XXII) is KOCN.

[0538] Particularly preferred pyridyl ethers of the formula (I.ak.19) can be prepared from compounds of the formula (XVIII.ak.19) in analogy to method F above:

[0539]

[0540] Preferably the isocyanate salt (XXII) is KOCN.

[0541] Pyridyl ethers (I.ak) are also preferred, particularly preferably pyridyl ethers of formula (I.al.1) to (I.al.36) as defined above are obtainable from compounds of formula (XVIII.al) in which R 1 , R 2 , R 3 and R 4 As defined herein, preferably as defined in Table A above:

[0542]

[0543] Preferably the isocyanate salt (XXII) is KOCN.

[0544] Particularly preferred pyridyl ethers of formula (I.a1.19) can be prepared analogously to method F above from compounds of formula (XVIII.a1.19):

[0545]

[0546] Preferably the isocyanate salt (XXII) is KOCN.

[0547] The intermediates required for the preparation of the pyridyl ethers of formula (I) according to the invention and mentioned in the above processes AF are commercially available or can be prepared by standard methods of organic chemistry, for example by the following methods:

[0548] Depending on the nature of the radical Y defined in methods C, D and E, the pyridines of the formula (II) required for method A above can be obtained analogously to method C from aminopyridines (XIX) or analogously to methods D or E from pyridines (X).

[0549] Alternatively, the pyridine of formula (II) can be prepared by reacting a compound of formula (X) with a reagent of formula (XI) in the presence of a base:

[0550]

[0551] In the compound of formula (X), L 4It is a leaving group such as halogen, C1-C6 alkylsulfonate or arylsulfonate; preferably F, Cl, C1-C6 alkylsulfonate or arylsulfonate; especially preferably F, Cl, OSO2CH3 or OSO2C6H4CH3; more preferably F or Cl.

[0552] The compounds of the formula (III) required in process A for preparing pyridyl ethers of the formula (I) are commercially available or known from the literature.

[0553] The compound of formula (IV) (required for the above method B) can be prepared by deprotecting the corresponding compound of formula (XII):

[0554]

[0555] In the compound of formula (XII), "PG" is selected from C1-C6 alkyl, C1-C6 cyanoalkyl, C1-C6 haloalkyl, C1-C6 alkylthio-C1-C4 alkyl, C1-C6 alkoxy-C1-C4 alkyl, C1-C6 alkoxy-C1-C4 alkoxy-C1-C4 alkyl, tri-C1-C6 alkylsilyl-C1-C4 alkyl, tri-C1-C6 alkylsilyl-C1-C4 alkoxy-C1-C4 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C4 The protecting groups of the present invention include but are not limited to C1-C6 alkyl, C5-C6 cycloalkenyl, tetrahydropyranyl, tri-C1-C6 alkylsilyl, (diphenyl)(C1-C4 alkyl)silyl, formyl, C1-C6 alkylcarbonyl, C1-C6 alkyl-O-carbonyl, C2-C6 alkenyl-O-carbonyl, (diphenyl)(C1-C4 alkyl)silyl-C1-C4 alkyl, phenyl-C1-C4 alkyl, phenylthio-C1-C6 alkyl, phenylcarbonyl, wherein each phenyl ring may be substituted by 1-3 substituents selected from halogen, CN, NO2, C1-C4 alkyl and C1-C4 alkoxy.

[0556] Preferably, PG is C1-C6 alkyl, C1-C6 alkoxy-C1-C4 alkyl, tri-C1-C6 alkylsilyl-C1-C4 alkyl, C2-C6 alkenyl, tetrahydropyranyl, tri-C1-C6 alkylsilyl, (diphenyl)(C1-C4 alkyl)silyl or phenyl-C1-C4 alkyl.

[0557] For example, the compound of formula (IV) can be prepared by reacting the compound in a solvent such as dichloromethane, acetonitrile or 1,4-dichloromethane. The compound of formula (XII) wherein "PG" is methyl is prepared by treating the compound of formula (XII) wherein "PG" is methyl with boron tribromide in oxane or without solvent at a temperature of 0-150°C.

[0558] Alternatively, the compound of formula (IV) can be prepared by deprotecting a compound of formula (XII) wherein "PG" is benzyl by catalytic hydrogenation in a hydrogen atmosphere at a pressure of 70-700 kPa, preferably 270-350 kPa, in the presence of a metal catalyst such as palladium supported on an inert support such as activated carbon suspended in a solvent such as ethanol at ambient temperature, wherein the weight ratio of metal to support is 5-20%.

[0559] The use and selection of protecting groups will be apparent to those skilled in chemical synthesis (see, for example, Greene, TW; Wuts, PGM Protective Groups in Organic Synthesis, 4th ed.; Wiley: New York, 2007).

[0560] The alkylating agents of the formula (V) required for process B above are commercially available or known from the literature.

[0561] The compound of formula (VI) (required for the above method C) can be obtained from the corresponding pyridines of formula (XIII):

[0562]

[0563] In the pyridines of formula (XIII), the group "PGN" is a protected amine substituent selected from N3, an aliphatic or aromatic carbamate, an aliphatic or aromatic amide, an N-C1-C6 alkylamine, an N-arylamine or a heteroarylamide.

[0564] Preferably, PGN is selected from N3, C1-C6 alkyl-O(CO)NH-, C1-C6 haloalkyl-O(CO)-NH-, tri-C1-C6 alkyl-Si-C1-C6 alkyl-O(CO)NH-, C2-C6 alkenyl-O(CO)NH-, C3-C6 alkynyl-O(CO)NH-, C3-C6 cycloalkyl-O(CO)NH-, fluorenylmethyl-O(CO)NH-, H(CO)N-, C1-C6 alkyl-(CO)-NH-, C1-C6 haloalkyl-(CO)-NH-, C1-C6 alkyl-NH, di-C1-C6 alkyl-N-, (C1-C6 alkoxy-C1-C6 alkyl)- C4 alkyl)NH-, di(C1-C6 alkoxy-C1-C4 alkyl)N-, C2-C6 alkenyl-NH, di(C2-C6 alkenyl)N-, tri-C1-C4 alkyl-Si-C1-C4 alkoxy-C1-C4 alkyl-NH-, di[tri-C1-C4 alkyl-Si-C1-C4 alkoxy-C1-C4 alkyl]N-, fluorenylmethyl-NH-, di(fluorenylmethyl)N-, N-phthalimide, N-2,3-dimethylmaleimide or N-2,5-dimethylpyrrole, phenyl-O(CO)NH-, phenyl-C1-C4 alkyl-O(CO)NH-, phenyl-(CO)NH-, phenyl- C1-C6 alkyl-(CO)NH-, pyridyl-(CO)-NH-, o-(C1-C4 alkoxy)phenyl-NH, di[o-(C1-C4 alkoxy)phenyl]N-, p-(C1-C4 alkoxy)phenyl-NH, di[p-(C1-C4 alkoxy)phenyl]N-, phenyl-C1-C4 alkyl-NH-, di(phenyl-C1-C4-alkyl)N-, p-(C1-C4 alkoxy)phenyl-C1-C4 alkyl-NH, di[p-(C1-C4 alkoxy)phenyl-C1-C4 alkyl]N-, wherein the phenyl or pyridyl rings can be substituted by 1-3 moieties selected from halogen, CN, NO2, C1-C4 alkoxy, The PGN is preferably selected from the group consisting of C1-C6 alkyl-O(CO)NH-, C1-C4 alkoxy, C1-C4 alkylsulfinyl and C1-C4 alkylsulfonyl; more preferably, PGN is selected from the group consisting of C1-C6 alkyl-O(CO)NH-, fluorenylmethyl-O(CO)NH-, H(CO)N-, C1-C6 alkyl-(CO)-NH-, C1-C6 haloalkyl-(CO)-NH, N-phthalimide, phenyl-O(CO)NH-, phenyl-C1-C4 alkyl-O(CO)NH-, phenyl-C1-C4 alkyl-NH-, di(phenyl-C1-C4 alkyl)N-, wherein the phenyl or pyridyl ring may each be substituted by 1-3 C1-C4 alkoxy substituents.

[0565] In the case where "PGN" is an azide substituent, pyridines of formula (XIII) may be converted to amines of formula (VI) using reductive reaction conditions such as zinc in aqueous ammonium chloride.

[0566] In the case where "PGN" is an acylated amine substituent, pyridines of formula (XIII) can be converted to amines of formula (VI) using an acid.

[0567] The use and selection of "PGN" substituents and appropriate deprotection methods are clear to those skilled in chemical synthesis (see, for example, Greene, TW; Wuts, PGM Protective Groups in Organic Synthesis, 4th edition; Wiley: New York, 2007).

[0568] The compounds of formula (VII) required for the preparation of pyridyl ethers of formula (I) can be prepared analogously to method A by reacting pyridine of formula (XIV) with a compound of formula (III) in the presence of a base:

[0569]

[0570] In the compound of formula (XIV), L 1 It is a leaving group such as halogen, C1-C6 alkylsulfonate or arylsulfonate; preferably F, Cl, C1-C6 alkylsulfonate or arylsulfonate; especially preferably F, Cl, OSO2CH3 or OSO2C6H4CH3; more preferably F or Cl.

[0571] L 3 It is a leaving group such as halogen or OSO2CF3; particularly preferably F, Cl or OSO2CF3; more preferably F or Cl.

[0572] As an alternative, the compounds of formula (VII) required for the preparation of pyridyl ethers of formula (I) can be prepared analogously to method B by reacting a pyridine of formula (XV) with a compound of formula (V) in the presence of a base:

[0573]

[0574] In the compound of formula (XV), L 3 It is a leaving group such as halogen or OSO2CF3; particularly preferably F, Cl or OSO2CF3; more preferably F or Cl.

[0575] The boronic acid, alkyl borate or Sn-tri(C1-C4 alkyl) of formula (VIII) required for preparing the compound of formula (I) in process D is commercially available, known from the literature or easily obtained from the following: 1 =Cl, Br or I corresponding compounds are prepared.

[0576] The compounds of formula (IX) required for the preparation of pyridyl ethers of formula (I) in process E are commercially available, known from the literature or can be readily prepared from the compounds wherein M2 =Cl, Br or I corresponding compounds are prepared.

[0577] The compounds of the formula (X) required for the preparation of the pyridines of the formula (II) are commercially available or known from the literature.

[0578] The compounds of the formula (XI) required for the preparation of the pyridines of the formula (II) are commercially available or known from the literature.

[0579] The compound of formula (XII) required for preparing the compound of formula (IV) can be prepared by reacting pyridine of formula (II) with a compound of formula (XVI) in the presence of a base in a similar manner to the above methods A and B:

[0580]

[0581] In compounds of formula (XVI), the group "PG" is a protecting group as defined above for compounds of formula (XII).

[0582] The pyridine of formula (XIII) (required for the preparation of the amine of formula (VI) above) can be prepared analogously to the above method A by reacting a compound of formula (XVII) with a compound of formula (III) (required for the above method A) in the presence of a base:

[0583]

[0584] In the compound of formula (XVII), L 5 It is a leaving group such as halogen, C1-C6 alkylsulfonate or arylsulfonate; preferably F, Cl, C1-C6 alkylsulfonate or arylsulfonate; especially preferably F, Cl, OSO2CH3 or OSO2C6H4CH3; more preferably F or Cl.

[0585] In compounds of formula (XVII), the group "PGN" is a protecting amine substituent as defined above for the amine of formula (XIII).

[0586] The compounds of the formula (XIV) required for the preparation of the compounds of the formula (VII) are commercially available or known from the literature.

[0587] The pyridine of formula (XV) required for synthesizing the compound of formula (VII) can be prepared by reacting the pyridine of formula (XIV) with the compound of formula (XVI) in the presence of a base and subsequently deprotecting:

[0588]

[0589] In compounds of formula (XVI), the group "PG" is a protecting group as defined above for compounds of formula (XII).

[0590] The use and selection of protecting groups and appropriate deprotection methods are apparent to those skilled in chemical synthesis (see, for example, Greene, TW; Wuts, PGM Protective Groups in Organic Synthesis, 4th edition; Wiley: New York, 2007).

[0591] The compounds of the formula (XVII) required for the synthesis of pyridines (XII) are commercially available or known from the literature.

[0592] Pyridines of formula (XV) (required for preparing compounds of formula (XVII) above) are commercially available or can be prepared from corresponding amines by known methods (see, for example, Greene, TW; Wuts, PGM Protective Groups in Organic Synthesis, 4th edition; Wiley: New York, 2007).

[0593] Compounds of formula (XVIII) (required for the above-mentioned process A) can be obtained from the corresponding amines of formula (XIX) and compounds of formula (XX) (eg EP 1 095 935):

[0594]

[0595] In the compound of formula (XX), L 6 It is a leaving group such as a C1-C6 alkoxy group or an aryloxy group, preferably a C1-C6 alkoxy group, and particularly preferably OCH3 or OC2H6.

[0596] The reaction of the amine of formula (XIX) with the compound of formula (XX) is generally carried out at a temperature from room temperature to the boiling point of the reaction mixture.

[0597] The reaction can in principle be carried out in bulk. However, preference is given to reacting the amine of the formula (XIX) with the compound of the formula (XX) in an organic solvent.

[0598] Suitable in principle are all solvents which are able to dissolve the amine of the formula (XIX) and the compound of the formula (XX) at least partially, preferably completely, under the reaction conditions.

[0599] Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8 paraffins; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-xylene, m-xylene and p-xylene; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), ... oxane, anisole and tetrahydrofuran (THF); nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone, diethyl ketone, tert-butyl methyl ketone, cyclohexanone; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol; and dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidone (NMP).

[0600] It is also possible to use mixtures of the solvents mentioned.

[0601] The by-product alcohol may be distilled off from the reaction mixture, or a small amount of an acid (eg, p-toluenesulfonic acid and methanesulfonic acid) or a base (eg, triethylamine, pyridine, potassium carbonate or sodium hydride) may be added to accelerate the reaction.

[0602] The completion of the reaction can be easily determined by the skilled worker by means of conventional methods.

[0603] The reaction mixture is worked up in a customary manner, for example by mixing with water, neutralization, separation of the phases and, if appropriate, purification of the crude product by chromatography.

[0604] Some of the intermediates and final products are obtained in the form of viscous oils which can be purified or freed from volatile components under reduced pressure and mildly elevated temperatures.

[0605] If the intermediates and end products are obtained as solids, they can also be purified by recrystallization or digestion.

[0606] Through R 15 The side reaction of the compound of formula (XVIII) with an amine of formula (XIX) can also give the following dimer of formula (XXI):

[0607]

[0608] Analogously to the above disclosure, dimers (XXI.ak.19) can be obtained by reacting amines of formula (XIX.ak.19) with compounds of formula (XVIII.ak.19):

[0609]

[0610] Likewise, dimers (XXI.al.19) can be obtained by reacting an amine of formula (XIX.al.19) with a compound of formula (XVIII.al.19):

[0611]

[0612] Amines of formula (XIX) required for the preparation of compounds of formula XVIII can be obtained analogously to the methods described in WO 17 / 202768 for amines of formula (XI).

[0613] The compound of formula (XX) is commercially available.

[0614] Isocyanate salt (XXII) is commercially available.

[0615] In order to broaden the spectrum of action and achieve synergistic effects, the pyridyl ethers of the formula (I) can be mixed with representatives of a large number of other herbicidal or growth-regulating active ingredient groups and subsequently applied simultaneously. Suitable components of the mixture are, for example, herbicides selected from the following classes: acetamides, amides, aryloxyphenoxypropionic esters, benzamides, benzofurans, benzoic acids, benzothiadiazinones, bipyridyls , carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenols, diphenyl ethers, glycines, imidazolinones, isocyanates Azoles, isocyanates Oxazolidinones, nitriles, N-phenylphthalimides, Oxadiazoles, Oxazolidinediones, glycolamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoramidates, phosphorodithioates, o-carbamoylbenzoates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylates, pyridinecarboxamides, pyrimidinediones, pyrimidyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils, ureas.

[0616] Furthermore, it may be useful to apply the pyridyl ethers of formula (I) alone or in combination with other herbicides or in the form of a mixture with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with inorganic salt solutions for treating nutrient and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.

[0617] In one embodiment of the invention, the compositions according to the invention comprise at least one pyridyl ether of the formula (I) (compound A) and at least one further active compound selected from the herbicides B, preferably herbicides B of groups b1) to b15), and safeners C (compound C).

[0618] In a further embodiment of the invention, the compositions according to the invention comprise at least one pyridyl ether of the formula (I) and at least one further active compound B (herbicide B).

[0619] The further herbicidal compound B (component B) is preferably selected from the herbicides of groups b1) to b15):

[0620] b1) lipid biosynthesis inhibitors;

[0621] b2) acetolactate synthase inhibitors (ALS inhibitors);

[0622] b3) photosynthesis inhibitors;

[0623] b4) protoporphyrinogen-IX oxidase inhibitors,

[0624] b5) bleaching agent herbicides;

[0625] b6) Enolpyruvylshikimate 3-phosphate synthase inhibitors (EPSP inhibitors);

[0626] b7) glutamine synthetase inhibitors;

[0627] b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);

[0628] b9) mitotic inhibitors;

[0629] b10) Very long chain fatty acid synthesis inhibitors (VLCFA inhibitors);

[0630] b11) cellulose biosynthesis inhibitors;

[0631] b12) Decoupler herbicides;

[0632] b13) auxin herbicides;

[0633] b14) auxin transport inhibitors; and

[0634] b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobe nzanid), flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, chlorine Oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and their salts and esters;

[0635] Including agriculturally acceptable salts or derivatives thereof.

[0636] Preference is given to those compositions according to the invention which comprise at least one herbicide B selected from the group consisting of the herbicides of classes b2, b3, b4, b5, b6, b7, b9, b10 and b13.

[0637] Particular preference is given to those compositions according to the invention which comprise at least one herbicide B selected from the group consisting of the herbicides of classes b4, b6, b7, b9, b10 and b13.

[0638] Particular preference is given to those compositions according to the invention which comprise at least one herbicide B selected from the herbicides of the classes b4, b6, b10 and b13.

[0639] Examples of herbicides B that can be used in combination with the pyridyl ethers of formula (I) of the present invention are:

[0640] b1) lipid biosynthesis inhibitors selected from the following: ACC herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, Fenoxaprop-ethyl, high Fenoxaprop-P, high fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, Metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6), 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3), 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5), 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3), 5-acetoxy-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6), 5-acetoxy-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one, 5-acetoxy-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1), 5-acetoxy-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1033760-55-2), 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1033760-55-2),6-Tetramethyl-5-oxo-2H-pyran-3-ylcarboxylic acid methyl ester (CAS 1312337-51-1), 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarboxylic acid methyl ester, 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarboxylic acid methyl ester (CAS1312340-83-2), 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarboxylic acid methyl ester (CAS 1033760-58-5); and non-ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;

[0641] b2) ALS inhibitors selected from the group consisting of sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, hyl), ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium thyl-sodium), iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, fluoropropyl prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl,trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron, imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumets ulam), florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam, pyrimidinyl benzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoic acid 1-methylethyl ester (CAS 420138-41-6), propyl 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzylamine (CAS 420138-01-8), sulfonylaminocarbonyltriazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl, and triafamone; wherein preferred embodiments of the present invention relate to those compositions comprising at least one imidazolinone herbicide;,

[0642] b3) photosynthesis inhibitors selected from the group consisting of amicarbazone, inhibitors of photosystem II, for example 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisothiazolin- oxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisothiazolin-3-yl)- 1-(5-tert-butyl-1-methylpyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methylpyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS1701416-69-4), 4-hydroxy-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidin-2-one (CAS1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-trifluoromethylpyrazol-3-yl]imidazolidin-2-one (CAS2023785-80-8), 1-(5-tert-butylisothiazolin-1-yl) ... oxazolidin-3-yl)-4-ethoxy-5-hydroxy-3-methylimidazolidin-2-one (CAS 1844836-64-1), triazine herbicides, including chlorotriazines, triazinones, triazinediones, methylthiotriazines and pyridazinones, such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin uzin), prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, and trietazin; aryl ureas such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thidiazuron, phenyl carbamates such as desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl ), nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uracils such as bromacil, lenacil and terbacil, as well as bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil and photosystem I inhibitors such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate. Preferred embodiments of the invention relate to those compositions comprising at least one aryl urea herbicide. Preferred embodiments of the invention likewise relate to those compositions comprising at least one triazine herbicide. Among the preferred embodiments of the present invention are also directed to those compositions comprising at least one nitrile herbicide;

[0643] b4) a protoporphyrinogen-IX oxidase inhibitor selected from the group consisting of acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlormethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flu flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, propargyl Oxadiargyl, oxadiazon, oxyfluorfen, ammonium pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4] oxazine-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[b][1,4] oxazine-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione (CAS1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4] oxazine-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), (E)-4-[2-chloro-5-(4-chloro-5-difluoromethoxy-1H-methylpyrazol-3-yl)-4-fluorophenoxy]-3-methoxybut-2-enoic acid methyl ester (CAS 948893-00-3) and 3-[7-chloro-5-fluoro-2-trifluoromethyl-1H-benzoimidazol-4-yl]-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (CAS 212754-02-4; preferably acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, fluorine flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, propargyl Oxadiargyl, oxadiazon, oxyfluorfen, ammonium pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4] oxazine-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[b][1,4] oxazine-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione (CAS1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4] oxazine-6-yl)-1H-pyrimidine-2,4-dione (CAS1304113-05-0), (E)-4-[2-chloro-5-(4-chloro-5-difluoromethoxy-1H-methylpyrazol-3-yl)-4-fluorophenoxy]-3-methoxybut-2-enoic acid methyl ester (CAS 948893-00-3) and 3-[7-chloro

[0644] -5-fluoro-2-trifluoromethyl-1H-benzimidazol-4-yl]-1-methyl-6-trifluoromethyl-1H-pyrimidine

[0645] -2,4-dione (CAS 212754-02-4);

[0646] b5) from the group consisting of the following bleaching agent herbicides: PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintrione, isoquinone isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, bleaching agent, unknown target: aclonifen, amitrole, flumeturon, 2-chloro-3-methylthio-N-(1-methyltetrazol-5-yl)-4-trifluoromethylbenzamide (CAS1361139-71-0), 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isothiazolylpyridine Oxazolidinone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-iso Oxazolidinone (CAS 81778-66-7);

[0647] b6) EPSP synthase inhibitors selected from the group consisting of glyphosate, glyphosate-isopropylammonium, glyphosate potassium and glyphosate-trimesium (sulfosate);

[0648] b7) glutamine synthetase inhibitors selected from the group consisting of bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammonium;

[0649] b8) DHP synthase inhibitors selected from the group consisting of asulam;

[0650] b9) is selected from the group consisting of the following mitotic inhibitors: K1 group compounds: dinitroanilines such as benfluralin, butralin, diinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, aminophosphorus esters such as amiprophos, amiprophos-methyl and butamiphos, benzoic acid herbicides such as chlorthal, chl orthal-dimethyl), pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam, K2 group compounds: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham; among them, K1 group compounds are preferred, and dinitroanilines are particularly preferred;

[0651] b10) is selected from the group consisting of the following VLCFA inhibitors: chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethanamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethanamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, and naphthamide-M, tetrazolinones such as fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isopropanols of formula II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9. Oxazoline compounds:

[0652]

[0653]

[0654] The isocyanate of formula (II) Oxazoline compounds are known in the art, for example from WO 2006 / 024820, WO 2006 / 037945, WO 2007 / 071900 and WO 2007 / 096576;

[0655] Among VLCFA inhibitors, chloroacetamides and hydroxyacetamides are preferred;

[0656] b11) a cellulose biosynthesis inhibitor selected from the group consisting of chlorthiamid, dichlobenil, flupoxam, indazine fluaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorophenoxy-1- 4 -[1,2,4,6]thiatriazine-3-ylamine (CAS 175899-01-1);

[0657] b12) a decoupler herbicide selected from the group consisting of dinoseb, dinoterb and DNOC and its salts;

[0658] b13) is selected from the following auxin herbicides: 2,4-D and its salts and esters, such as clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxy-propyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, Fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS943832-60-8), MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters , picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6);

[0659] b14) an auxin transport inhibitor selected from the group consisting of diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;

[0660] b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethoate, hipin), sodium arsenic acid (DSMA), dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleichydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methylazide, methyl bromide, methyl-dymron, methyliodide, monosodium arsenic acid (MSMA), oleic acid, chlorine oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine and tridiphane.

[0661] The active compounds B and C having a carboxyl group can be used in the compositions according to the invention in the form of the acid, in the form of agriculturally acceptable salts or in the form of agriculturally acceptable derivatives, as described above.

[0662] In the case of dicamba, suitable salts include those in which the counterion is an agriculturally available cation. For example, suitable salts of dicamba are dicamba sodium (dicamba-sodium), dicamba potassium (dicamba-potassium), dicamba methylammonium (dicamba-methylammonium), dicamba dimethylammonium (dicamba-dimethylammonium), dicamba isopropylammonium (dicamba-isopropylammonium), dicamba diglycolamine (dicamba-diglycolamine), dicamba ethanolamine (dicamba-olamine), dicamba diethanolamine (dicamba-diolamine), dicamba triethanolamine (dicamba-trolamine), dicamba-N, N-bis (3-aminopropyl) methylamine and dicamba-diethylenetriamine. The example of suitable ester is dicamba methyl ester (dicamba-methyl) and dicamba butoxyethyl ester (dicamba-butoyl).

[0663] Suitable salts of 2,4-D are 2,4-D ammonium, 2,4-D dimethylammonium, 2,4-D diethylammonium, 2,4-D diethanolammonium (2,4-D diolamine), 2,4-D triethanolammonium, 2,4-D isopropylammonium, 2,4-D triisopropanolammonium, 2,4-D heptylammonium, 2,4-D dodecylammonium, 2,4-D tetradecylammonium, 2,4-D triethylammonium, 2,4-D tri(2-hydroxypropyl)ammonium, 2,4-D triisopropylammonium, 2,4-D triethanolamine, 2,4-D lithium, 2,4-D sodium and 2,4-DN,N,D. N-trimethylethanolammonium (2,4-D choline), preferably 2,4-D ammonium, 2,4-D dimethylammonium, 2,4-D diethylammonium, 2,4-D diethanolammonium (2,4-D diolamine), 2,4-D triethanolammonium, 2,4-D isopropylammonium, 2,4-D triisopropanolammonium, 2,4-D heptylammonium, 2,4-D dodecylammonium, 2,4-D tetradecylammonium, 2,4-D triethylammonium, 2,4-D tri(2-hydroxypropyl)ammonium, 2,4-D triisopropylammonium, 2,4-D triethanolamine, 2,4-D lithium, 2,4-D sodium. Examples of suitable esters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl ...isooctyl, 2,4-D-butyl, 2,4-D-ethyl tyl), 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.

[0664] Suitable salts of 2,4-DB are, for example, 2,4-DB sodium, 2,4-DB potassium, and 2,4-DB dimethylammonium. Suitable esters of 2,4-DB are, for example, 2,4-DB butyl and 2,4-DB isooctyl.

[0665] Suitable salts of dichlorprop are, for example, dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop-butotyl and dichlorprop-isoctyl.

[0666] Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, and MCPA-triethanolamine.

[0667] A suitable salt of MCPB is sodium MCPB. A suitable ester of MCPB is MCPB-ethyl.

[0668] Suitable salts of clopyralid are clopyralid-potassium, clopyralid-ethanolammonium and clopyralid-tri-(2-hydroxypropyl)ammonium. An example of a suitable ester of clopyralid is clopyralid-methyl ester.

[0669] Examples of suitable esters of fluroxypyr are fluroxypyr-2-butoxy-1-methylethyl, of which fluroxypyr-2-butoxy-1-methylethyl is preferred.

[0670] Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable ester of picloram is picloram-isoctyl.

[0671] A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are, for example, triclopyr-ethyl and triclopyr-butotyl.

[0672] Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA dimethylammonium, 2,3,6-TBA lithium, 2,3,6-TBA potassium and 2,3,6-TBA sodium.

[0673] Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid-dimethylammonium and aminopyralid-tris(2-hydroxypropyl)ammonium.

[0674] Suitable salts of glyphosate are, for example, glyphosate-ammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-isopropylamine, glyphosate-potassium, glyphosate-sodium, glyphosate-sulfosate and ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylamine and glyphosate-sulfosate.

[0675] A suitable salt of glufosinate is for example glufosinate ammonium.

[0676] A suitable salt of glufosinate-P is, for example, glufosinate-P-ammonium.

[0677] Suitable salts and esters of bromoxynil are, for example, bromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.

[0678] Suitable salts and esters of ioxonil are, for example, ioxonil-octanoate, ioxonil-potassium and ioxonil-sodium.

[0679] Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.

[0680] Suitable salts of mecoprop-P are, for example, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.

[0681] A suitable salt of diflupyrone is, for example, diflupyrone sodium.

[0682] A suitable salt of naptalam is, for example, naptalam-sodium.

[0683] Suitable salts and esters of cyprodinil acid are, for example, dimethylammonium cyprodinil, methyl cyprodinil ester, triisopropanolammonium cyprodinil, sodium cyprodinil and potassium cyprodinil.

[0684] A suitable salt of quinclorac is, for example, dimethylammonium quinclorac.

[0685] A suitable salt of quinmerac is, for example, quinmerac dimethylammonium.

[0686] A suitable salt of imazamox is, for example, imazamox ammonium.

[0687] Suitable salts of imazapic are, for example, imazapic ammonium and imazapic isopropylammonium.

[0688] Suitable salts of methapyr are, for example, methapyr ammonium and methapyr isopropylammonium.

[0689] A suitable salt of mefenacet is for example mefenacet-ammonium.

[0690] Suitable salts of imazethapyr are, for example, imazethapyr ammonium and imazethapyr isopropylammonium.

[0691] A suitable salt of topravir is, for example, topravir sodium.

[0692] Particularly preferred herbicides B are the herbicides B as defined above; in particular the herbicides B.1 to B.203 listed below in Table B, preferably the herbicides B.1 to B.202:

[0693] Table B:

[0694]

[0695]

[0696]

[0697]

[0698] In addition, it may be useful to apply the pyridyl ethers of formula (I) in combination with safeners. Safeners are compounds that prevent or reduce damage to useful plants but do not have a significant effect on the herbicidal action of the pyridyl ethers of formula (I) on unwanted plants. They can be applied before sowing (for example during seed treatment, on shoots or rice seedlings) or in a pre-emergence or post-emergence application of useful plants. Safeners and pyridyl ethers of formula (I) and optionally, herbicide B can be applied simultaneously or sequentially.

[0699] In a further embodiment of the present invention, the compositions according to the invention comprise at least one pyridyl ether of the formula (I) and at least one safener C (component C).

[0700] Suitable safeners are, for example, (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, 4,5-dihydro-5,5-diaryl-3-isothiazolyl-1H- azolecarboxylic acid, dichloroacetamides, α-oximinophenylacetonitrile, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1,8-naphthalene dicarboxylic anhydride, 2-halo-4-haloalkyl-5-thiazolecarboxylic acids, thiophosphates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such as amides, esters and thioesters, provided that they have an acid group.

[0701] Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, diphenyl isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-dichloroacetyl-1,3- Oxazolidine (R-29148, CAS 52836-31-4), metcamifen (CAS 129531-12-0) and BPCMS.

[0702] Particularly preferred safeners C as component C constituting an ingredient of the composition according to the invention are safeners C as defined above, in particular safeners C.1 to C.17 listed in the following Table C:

[0703] Table C

[0704]

[0705] The active compounds B and active compounds C of groups b1) to b15) are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000, Volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, RR Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart, 1995; WH Hanens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994 and KK Hatzios, Herbicide Handbook, 7th edition supplement, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-dichloroacetyl-1,3- Oxazolidine [CAS No. 52836-31-4] is also known as R-29148. 4-Dichloroacetyl-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also known as AD-67 and MON 4660.

[0706] The assignment of the respective mechanism of action of the active compounds is based on current knowledge. If several mechanisms of action apply to an active compound, the substance is only assigned to one mechanism of action.

[0707] According to a preferred embodiment of the invention, the composition comprises as herbicidally active compound B or component B at least one, preferably exactly one, herbicide B.

[0708] According to a further preferred embodiment of the invention, the composition comprises as herbicidally active compounds B or components B at least two, preferably exactly two herbicides B which are different from one another.

[0709] According to a further preferred embodiment of the invention, the composition comprises as herbicidally active compounds B or components B at least three, preferably exactly three herbicides B which are different from one another.

[0710] According to a further preferred embodiment of the invention, the composition comprises as herbicidally active compounds B or components B at least four, preferably exactly four herbicides B which are different from one another.

[0711] According to a further preferred embodiment of the invention, the composition comprises as safening component C or component C at least one, preferably exactly one safener C.

[0712] According to a further preferred embodiment of the invention, the composition comprises as component B at least one, preferably exactly one, herbicide B and as component C at least one, preferably exactly one, safener C.

[0713] According to a further preferred embodiment of the invention, the composition comprises as component C at least two, preferably exactly two, herbicides B that are different from one another and at least one, preferably exactly one, safener C.

[0714] According to a further preferred embodiment of the invention, the composition comprises as component C at least three, preferably exactly three, herbicides B that are different from one another and at least one, preferably exactly one, safener C.

[0715] According to another preferred embodiment of the present invention, the composition comprises as component A at least one, preferably exactly one, compound of formula (I), preferably a compound of formula (Ia), (Ib), (Ie), (Il), (Im), (In), (Io), (Ip), (Iq), (Is), (It), (Iw), (I.ac), (I.ad), (I.ae), (I.af), (I.ag) or (I.ah) and as component B at least one, preferably exactly one, herbicide B.

[0716] According to another preferred embodiment of the present invention, the composition comprises at least one, preferably exactly one, compound of formula (I), preferably a compound of formula (Ia), (Ib), (Ie), (Il), (Im), (In), (Io), (Ip), (Iq), (Is), (It), (Iw), (I.ac), (I.ad), (I.ae), (I.af), (I.ag) or (I.ah) as component A and at least two, preferably exactly two herbicides B that are different from each other.

[0717] According to another preferred embodiment of the present invention, the composition comprises at least one, preferably exactly one, compound of formula (I), preferably a compound of formula (Ia), (Ib), (Ie), (Il), (Im), (In), (Io), (Ip), (Iq), (Is), (It), (Iw), (I.ac), (I.ad), (I.ae), (I.af), (I.ag) or (I.ah) as component A and at least three, preferably exactly three different herbicides B.

[0718] According to another preferred embodiment of the present invention, the composition comprises at least one, preferably exactly one, compound of formula (I), preferably a compound of formula (Ia), (Ib), (Ie), (Il), (Im), (In), (Io), (Ip), (Iq), (Is), (It), (Iw), (I.ac), (I.ad), (I.ae), (I.af), (I.ag) or (I.ah) as component A and at least four, preferably exactly four different herbicides B.

[0719] According to another preferred embodiment of the present invention, the composition comprises at least one, preferably exactly one, compound of formula (I), preferably a compound of formula (Ia), (Ib), (Ie), (Il), (Im), (In), (Io), (Ip), (Iq), (Is), (It), (Iw), (I.ac), (I.ad), (I.ae), (I.af), (I.ag) or (I.ah) as component A and at least one, preferably exactly one, safener C as component C.

[0720] According to another preferred embodiment of the present invention, the composition comprises as component A at least one, preferably exactly one, compound of formula (I), preferably a compound of formula (Ia), (Ib), (Ie), (Il), (Im), (In), (Io), (Ip), (Iq), (Is), (It), (Iw), (I.ac), (I.ad), (I.ae), (I.af), (I.ag) or (I.ah), at least one, preferably exactly one, herbicide B as component B and at least one, preferably exactly one, safener C as component C.

[0721] According to another preferred embodiment of the present invention, the composition comprises as component A at least one, preferably exactly one, compound of formula (I), preferably a compound of formula (Ia), (Ib), (Ie), (Il), (Im), (In), (Io), (Ip), (Iq), (Is), (It), (Iw), (I.ac), (I.ad), (I.ae), (I.af), (I.ag) or (I.ah), at least two, preferably exactly two herbicides B that are different from each other and at least one, preferably exactly one, safener C as component C.

[0722] According to another preferred embodiment of the present invention, the composition comprises as component A at least one, preferably exactly one, compound of formula (I), preferably a compound of formula (Ia), (Ib), (Ie), (Il), (Im), (In), (Io), (Ip), (Iq), (Is), (It), (Iw), (I.ac), (I.ad), (I.ae), (I.af), (I.ag) or (I.ah), at least three, preferably exactly three mutually different herbicides B and at least one, preferably exactly one, safener C as component C.

[0723] According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridyl ether of formula (I), in particular selected from the group consisting of (Ia18), (Ia19), (Ie18), (Ie19), (Il18), (Il19), (In18), (In19), (Io18), (Io19), (Iq18), (Iq19), (Is18), (Is19), (Iw18), (Iw19), (I.ac.18), (I.ac.19), (I.ae.18), (I.ae.19), (I.af.18), (I.af.19), (I.ah.18) and (I.ah.19), at least one, in particular exactly one, selected from group b4), in particular selected from the group consisting of acifluorfen, butafencil, carfenetrazone-ethyl, fluazifop-butyl, Oxazine, Fensulfuron, Propargyl The herbicidally active compounds are pyraflufen, oxyfluorfen-butyl, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfamethoxazole, trifludimoxazine, and ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100).

[0724] According to another preferred embodiment of the invention, the composition comprises, in addition to the pyridyl ether of formula (I), in particular an active compound selected from (Ia18), (Ia19), (Ie18), (Ie19), (Il18), (Il19), (In18), (In19), (Io18), (Io19), (Iq18), (Iq19), (Is18), (Is19), (Iw18), (Iw19), (I.ac.18), (I.ac.19), (I.ae.18), (I.ae.19), (I.af.18), (I.af.19), (I.ah.18) and (I.ah.19), at least one, in particular exactly one, herbicidally active compound selected from group b6), in particular selected from glyphosate, ammonium glyphosate, dimethyl glyphosate, isopropylamine glyphosate, sulfosate and potassium glyphosate.

[0725] According to another preferred embodiment of the present invention, the composition, in addition to the pyridyl ether of formula (I), is especially selected from (Ia18), (Ia19), (Ie18), (Ie19), (Il18), (Il19), (In18), (In19), (Io18), (Io19), (Iq18), (Iq19), (Is18), (Is19), (Iw18), (Iw19), (I.ac.18), (I.ac.19), (I.ae.18), In addition to the active compounds of (I.ae.19), (I.af.18), (I.af.19), (I.ah.18) and (I.ah.19), the herbicidally active compound comprises at least one, in particular exactly one, selected from group b10), in particular selected from sethoxydim, butachlor, mesotrione, dimethoate, tetrazopyralid, flufenacet, mefenacet, metabazone, isopropylamine, S-isopropylamine, fenoxasulfone, ipfencarbazone and pyroxasulfone. Likewise preferred is the presence of at least one, in particular exactly one, isocyanate selected from group b10), in particular from the group consisting of pyridyl ethers of formula (I), in particular from the group consisting of (Ia18), (Ia19), (Ie18), (Ie19), (Il18), (Il19), (In18), (In19), (Io18), (Io19), (Iq18), (Iq19), (Is18), (Is19), (Iw18), (Iw19), (I.ac.18), (I.ac.19), (I.ae.18), (I.ae.19), (I.af.18), (I.af.19), (I.ah.18) and (I.ah.19). Azoline compound having herbicidal activity.

[0726] According to another preferred embodiment of the present invention, the composition, in addition to the pyridyl ether of formula (I), is especially selected from (Ia18), (Ia19), (Ie18), (Ie19), (Il18), (Il19), (In18), (In19), (Io18), (Io19), (Iq18), (Iq19), (Is18), (Is19), (Iw18), (Iw19), (I.ac.18), (I.ac.19), (Iae.18 ), (I.ae.19), (I.af.18), (I.af.19), (I.ah.18) and (I.ah.19) contain at least one, in particular exactly one, selected from group b13), in particular selected from 2,4-D, 2,4-D isobutyl ester, 2,4-D dimethylammonium, 2,4-DN,N,N-trimethylethanolammonium, cyproconazole acid, cyproconazole potassium, cyproconazole methyl ester, aminopyralid, aminopyralid methyl ester, aminopyralid dimethylammonium salt, aminopyralid isopropanol ammonium salt, Clopicomac acid, clopicomac acid methyl ester, clopicomac acid ethanolammonium, dicamba, dicamba butoxyethyl ester, dicamba diglycolamine, dicamba dimethylammonium, dicamba diethanolamine, dicamba isopropylammonium, dicamba potassium, dicamba sodium, dicamba triethanolamine, dicamba-N,N-di(3-aminopropyl)methylamine, dicamba-diethylenetriamine, flopyrauxifen, fluroxypyr, fluchloramine, halauxifen, halauxifen (halauxifen), en-methyl), MCPA, MCPA-2-ethylhexyl ester, MCPA dimethylammonium, dichloroquinoline, dichloroquinoline dimethylammonium, quinclorac, quinclorac dimethylammonium, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid.

[0727] Here and hereinafter, the term "dual composition" encompasses compositions comprising one or more, for example 1 , 2 or 3, active compounds of the formula (I) and one or more, for example 1 , 2 or 3, herbicides B or one or more safeners C.

[0728] Correspondingly, the term "ternary composition" embraces compositions comprising one or more, for example 1, 2 or 3, active compounds of formula (I), one or more, for example 1, 2 or 3 herbicides B and one or more, for example 1, 2 or 3 safeners C.

[0729] In binary compositions comprising at least one compound of the formula (I) as component A and at least one herbicide B, the weight ratio of active compound A:B is generally 1:1000-1000:1, preferably 1:500-500:1, in particular 1:250-250:1, particularly preferably 1:125-125:1.

[0730] In binary compositions comprising at least one compound of the formula (I) as component A and at least one safener C, the weight ratio of active compound A:C is generally 1:1000-1000:1, preferably 1:500-500:1, in particular 1:250-250:1, particularly preferably 1:75-75:1.

[0731] In ternary compositions comprising at least one pyridyl ether of formula (I) as component A, at least one herbicide B and at least one safener C, the relative weight ratio of component A:B is generally 1:1000-1000:1, preferably 1:500-500:1, especially 1:250-250:1, particularly preferably 1:125-125:1, the weight ratio of component A:C is generally 1:1000-1000:1, preferably 1:500-500:1, especially 1:250-250:1, particularly preferably 1:75-75:1, and the weight ratio of component B:C is generally 1:1000-1000:1, preferably 1:500-500:1, especially 1:250-250:1, particularly preferably 1:75-75:1. The weight ratio of component A+B to component C is preferably 1:500-500:1, in particular 1:250-250:1, particularly preferably 1:75-75:1.

[0732] The weight ratios of the components in the preferred mixtures described below are within the limits given herein, especially within the preferred limits.

[0733] Particularly preferred are compositions comprising pyridyl ethers of formula (I) as defined and substances as defined in the corresponding row of Table 1; particularly preferred are compositions comprising pyridyl ethers of formula (I) as defined and substances as defined in the corresponding row of Table 1 as the only herbicidally active compounds; most preferred are compositions comprising pyridyl ethers of formula (I) as defined and substances as defined in the corresponding row of Table 1 as the only active compounds.

[0734] Particularly preferred are compositions 1.1 to 1.3671, especially compositions 1.1 to 1.3653, which comprise a pyridyl ether (Ia.18) and a substance as defined in the corresponding row of Table 1:

[0735] Table 1 (composition 1.1-1.3671):

[0736]

[0737]

[0738]

[0739]

[0740]

[0741]

[0742]

[0743]

[0744]

[0745]

[0746]

[0747]

[0748]

[0749]

[0750]

[0751]

[0752]

[0753]

[0754]

[0755]

[0756]

[0757]

[0758]

[0759]

[0760]

[0761]

[0762] The specific numbering of each single composition is derived as follows:

[0763] Composition 1.200 comprises, for example, pyridyl ether Ia18 and cypermethrin (B.200) (see Table 1, entry 1.200; and Table B, entry B.200).

[0764] Composition 2.200 comprises, for example, pyridyl ether Ia19 (as defined below in compositions 2.1 to 2.3671, preferably 2.1 to 2.3653) and cypermethrin (B.200) (see Table 1, entry 1.200; and Table B, entry B.200).

[0765] Also especially preferred are compositions 2.1 to 2.3671, preferably 2.1. to 2.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Ia19).

[0766] Also especially preferred are compositions 3.1 to 3.3671, preferably 3.1. to 3.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Ie18).

[0767] Also especially preferred are compositions 4.1 to 4.3671, preferably 4.1. to 4.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Ie19).

[0768] Also especially preferred are compositions 5.1 to 5.3671, preferably 5.1. to 5.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Il18).

[0769] Also especially preferred are compositions 6.1 to 6.3671, preferably 6.1. to 6.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Il19).

[0770] Also especially preferred are compositions 7.1 to 7.3671, preferably 7.1. to 7.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (In18).

[0771] Also especially preferred are compositions 8.1 to 8.3671, preferably 8.1. to 8.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (In19).

[0772] Also especially preferred are compositions 9.1 to 9.3671, preferably 9.1. to 9.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Io18).

[0773] Also especially preferred are compositions 10.1 to 10.3671, preferably 10.1. to 10.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Io19).

[0774] Also especially preferred are compositions 11.1 to 11.3671, preferably 11.1. to 11.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Iq18).

[0775] Also especially preferred are compositions 12.1 to 12.3671, preferably 12.1. to 12.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Iq19).

[0776] Also especially preferred are compositions 13.1 to 13.3671, preferably 13.1. to 13.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Is18).

[0777] Also especially preferred are compositions 14.1 to 14.3671, preferably 14.1. to 14.3653, which differ from the corresponding compositions 1.1 to 1.3653, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Is19).

[0778] Also especially preferred are compositions 15.1 to 15.3671, preferably 15.1. to 15.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Iw18).

[0779] Also especially preferred are compositions 16.1 to 16.3671, preferably 16.1. to 16.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (Iw19).

[0780] Also especially preferred are compositions 17.1 to 17.3671, preferably 17.1. to 17.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (I.ac.18).

[0781] Also especially preferred are compositions 18.1 to 18.3671, preferably 18.1. to 18.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (I.ac.19).

[0782] Also especially preferred are compositions 19.1 to 19.3671, preferably 19.1. to 19.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (I.ae.18).

[0783] Also especially preferred are compositions 20.1 to 20.3671, preferably 20.1. to 20.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (I.ae.19).

[0784] Also especially preferred are compositions 21.1 to 21.3671 , more preferably 21.1. to 21.3653, which differ from the corresponding compositions 1.1 to 1.3671 , preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (I.af.18).

[0785] Also especially preferred are compositions 22.1 to 22.3671 , more preferably 22.1. to 22.3653, which differ from the corresponding compositions 1.1 to 1.3671 , preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (I.af.19).

[0786] Also especially preferred are compositions 23.1 to 23.3671, more preferably 23.1. to 23.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (I.ah.18).

[0787] Also especially preferred are compositions 24.1 to 24.3671 , more preferably 24.1. to 24.3653, which differ from the corresponding compositions 1.1 to 1.3671 , preferably 1.1 to 1.3653, only in that they comprise as active compound A a pyridyl ether of the formula (I.ah.19).

[0788] The invention furthermore relates to agrochemical compositions comprising at least one adjuvant and at least one pyridyl ether of the formula (I) according to the invention.

[0789] The agrochemical composition comprises a pyridyl ether of formula (I) in an insecticidal effective amount. The term "effective amount" means an amount of the composition or compound I sufficient to control unwanted plants, especially in crops (i.e. cultivated plants) without causing significant damage to the treated plants. This amount can vary within a wide range and depends on various factors such as the plants to be controlled, the crops or materials to be treated, climatic conditions and the specific pyridyl ether of formula (I) used.

[0790] The pyridyl ethers of formula (I), their N-oxides, salts or derivatives can be converted into types commonly used in agricultural chemical compositions, such as solutions, emulsions, suspensions, pulvis, powders, pastes, granules, molded products, capsules and mixtures thereof. Examples of agricultural chemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or pulvis (e.g. WP, SP, WS, DP, DS), molded products (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticide preparations (e.g. LN) and gel formulations (e.g. GF) for treating plant propagation materials such as seeds. These and other agricultural chemical composition types are defined in "Catalogue of pesticide formulation types and international coding system", Technical Monograph, No. 2, May 2008, 6th edition, CropLife International.

[0791] The agrochemical compositions are prepared in a known manner as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or by Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0792] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, tackifiers and adhesives.

[0793] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling mineral oil fractions, for example kerosene, diesel; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, for example toluene, paraffin, tetralin, alkylated naphthalenes; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example cyclohexanone; esters, for example lactic acid esters, carbonates, fatty acid esters, γ-butyrolactone; fatty acids; phosphonates; amines; amides, for example N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[0794] Suitable solid carriers or fillers are mineral earths, for example silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, for example cellulose, starch; fertilizers, for example ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of plant origin, for example cereal flour, bark flour, wood flour, nut shell flour, and mixtures thereof.

[0795] 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 emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids or adjuvants. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[0796] Suitable anionic surfactants are alkali metals, alkaline earth metals or ammonium salts of sulfonic acid, sulfuric acid, phosphoric acid, carboxylic acids and mixtures thereof. Examples of sulfonates are alkyl aryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalene, sulfonates of dodecyl- and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalene, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols or sulfates of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0797] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerides or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinyl pyrrolidone, vinyl alcohol or vinyl acetate.

[0798] 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 alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers comprising blocks of polyoxyethylene and polyoxypropylene, or ABC type block polymers comprising alkanol, polyoxyethylene and polyoxypropylene. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamine or polyvinylamine.

[0799] Suitable adjuvants are compounds which themselves have negligible pesticide activity or even no pesticide activity and which improve the biological performance of the pyridyl ethers of formula (I) on the target. Examples are surfactants, mineral or vegetable oils and other adjuvants. Other examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

[0800] Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[0801] Suitable fungicides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

[0802] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol.

[0803] Suitable defoamers are silicones, long-chain alcohols and fatty acid salts.

[0804] Suitable colorants (for example red, blue or green) are low water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (for example iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (for example alizarin colorants, azo colorants and phthalocyanine colorants).

[0805] Suitable tackifiers or adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, bio- or synthetic waxes and cellulose ethers.

[0806] Examples of types of agrochemical compositions and their preparation are:

[0807] i) Water-soluble concentrates (SL, LS)

[0808] 10-60% by weight of the pyridyl ether of formula (I) of the present invention or a herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) and 5-15% by weight of a wetting agent (e.g., alcohol alkoxylate) are dissolved in up to 100% by weight of water and / or a water-soluble solvent (e.g., alcohol). The active substance dissolves when diluted with water.

[0809] ii) Dispersible Concentrate (DC)

[0810] 5-25 wt % of the pyridyl ether of formula (I) of the present invention or a herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) and 1-10 wt % of a dispersant (e.g. polyvinyl pyrrolidone) are dissolved in an organic solvent (e.g. cyclohexanone) added to 100 wt %. Dilution with water gives a dispersion.

[0811] iii) Emulsifiable concentrates (EC)

[0812] 15-70 wt % of the pyridyl ether of formula (I) of the present invention or a herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) and 5-10 wt % of an emulsifier (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e.g. aromatic hydrocarbon) added to 100 wt %. The mixture is diluted with water to obtain an emulsion.

[0813] iv) Emulsion (EW, EO, ES)

[0814] 5-40 wt % of the pyridyl ether of formula (I) of the present invention or a herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) and 1-10 wt % of an emulsifier (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt % of a water-insoluble organic solvent (e.g. aromatic hydrocarbon). The mixture is introduced into 100 wt % of water by means of an emulsifier and made into a homogeneous emulsion. The emulsion is diluted with water to obtain an emulsion.

[0815] v) Suspension (SC, OD, FS)

[0816] In a stirred ball mill, 20-60% by weight of a pyridyl ether of the formula (I) according to the invention or a herbicidal composition comprising at least one pyridyl ether of the formula (I) (component A) and at least one other compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C) is ground under the addition of 2-10% by weight of dispersants and wetting agents (e.g. sodium lignin sulfonate and alcohol ethoxylate), 0.1-2% by weight of thickeners (e.g. xanthan gum) and up to 100% by weight of water to give a finely divided active substance suspension. Dilution with water gives a stable active substance suspension. For FS type compositions, up to 40% by weight of a binder (e.g. polyvinyl alcohol) is added.

[0817] vi) Water dispersible granules and water soluble granules (WG, SG)

[0818] 50-80% by weight of a pyridyl ether of the present invention of formula (I) or a herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one other compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C) is finely ground under the addition of up to 100% by weight of dispersants and wetting agents (e.g. sodium lignin sulfonate and alcohol ethoxylate) and is made into water-dispersible or water-soluble granules by means of industrial equipment (e.g. extruder, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

[0819] vii) Water dispersible powders and water soluble powders (WP, SP, WS)

[0820] 50-80% by weight of a pyridyl ether of the formula (I) according to the invention or a herbicidal composition comprising at least one pyridyl ether of the formula (I) (component A) and at least one other compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C) is ground in a rotor-stator mill with the addition of 1-5% by weight of a dispersant (e.g. sodium lignin sulfonate), 1-3% by weight of a wetting agent (e.g. alcohol ethoxylate) and up to 100% by weight of a solid carrier (e.g. silica gel). Dilution with water gives a stable dispersion or solution of the active substance. viii) Gel (GW, GF)

[0821] In a stirred ball mill, 5-25% by weight of a pyridyl ether of formula (I) according to the invention or a herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one other compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C) is ground under the addition of 3-10% by weight of a dispersant (e.g. sodium lignin sulfonate), 1-5% by weight of a thickener (e.g. carboxymethyl cellulose) and up to 100% by weight of water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

[0822] iv) Microemulsion (ME)

[0823] 5-20 wt % of the pyridyl ether of formula (I) according to the present invention or a herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) is added to 5-30 wt % of an organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt % of a surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate) and 100 wt % of water. The mixture is stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[0824] iv) Microcapsules (CS)

[0825] A herbicidal composition comprising 5-50% by weight of a pyridyl ether of formula (I) of the present invention or at least one pyridyl ether of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C), 0-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and 2-15% by weight of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Free radical polymerization initiated by a free radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50% by weight of a pyridyl ether of formula (I) of the present invention, 0-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon) and an isocyanate monomer (e.g., diphenylmethane-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer amount is 1-10 wt. %. The wt. % refers to the entire CS composition. ix) Dustable powders (DP, DS)

[0826] 1-10% by weight of a pyridyl ether of the formula (I) according to the invention or a herbicidal composition comprising at least one pyridyl ether of the formula (I) (component A) and at least one other compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C) is finely ground and intimately mixed with up to 100% by weight of a solid carrier (e.g. finely divided kaolin).

[0827] x) Particles (GR, FG)

[0828] 0.5-30% by weight of a pyridyl ether of formula (I) according to the invention or a herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) is finely ground and combined with up to 100% by weight of a solid carrier (e.g. a silicate). Granulation is achieved by extrusion, spray drying or fluidized bed.

[0829] xi) Ultra Low Volume Liquid (UL)

[0830] 1 to 50% by weight of a pyridyl ether of the formula (I) according to the present invention or a herbicidal composition comprising at least one pyridyl ether of the formula (I) (component A) and at least one other compound selected from the group consisting of herbicidal compounds B (component B) and safeners C (component C) is dissolved in up to 100% by weight of an organic solvent (e.g. an aromatic hydrocarbon).

[0831] Agrochemical compositions of types i) to xi) may optionally comprise further auxiliaries, such as 0.1 to 1% by weight of fungicides, 5 to 15% by weight of antifreeze agents, 0.1 to 1% by weight of antifoams and 0.1 to 1% by weight of colorants.

[0832] The agrochemical and / or herbicidal compositions generally contain 0.01-95% by weight, preferably 0.1-90% by weight, in particular 0.5-75% by weight of pyridyl ethers of formula (I). The pyridyl ethers of formula (I) are used in a purity of 90-100%, preferably 95-100% (according to NMR spectrum).

[0833] For the treatment of plant propagation materials, especially seeds, solutions (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 used. The agrochemical compositions give active substance concentrations of 0.01-60% by weight, preferably 0.1-40% by weight, in ready-to-use preparations after dilution 2-10 times. Application can be carried out before or during sowing.

[0834] The pyridyl ethers of formula (I), agricultural chemical compositions thereof and / or herbicidal compositions are applied to plant propagation materials, especially seeds, by methods of seed dressing, coating, granulation, dusting, soaking and in-furrow application of the propagation materials. Preferably, the pyridyl ethers of formula (I), agricultural chemical compositions thereof and / or herbicidal compositions are applied to the plant propagation materials respectively by a method that does not induce germination, such as seed dressing, granulation, coating and dusting.

[0835] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the pyridyl ethers of formula (I), the agrochemical compositions and / or herbicidal compositions containing them as premixes or, if appropriate, added immediately before use (tank mix). These agents can be mixed with the agrochemical compositions of the present invention in a weight ratio of 1:100-100:1, preferably 1:10-10:1.

[0836] The user usually uses the pyridyl ethers of formula (I) of the present invention, the agricultural chemical composition containing them and / or the herbicidal composition for a pre-dosage device, a small backpack sprayer, a spray tank, a spray plane or an irrigation system. Usually the agricultural chemical composition is formulated with water, a buffer and / or other adjuvants to the required application concentration, thereby obtaining a ready-to-use spray liquid or an agricultural chemical composition of the present invention. 20-2000 liters, preferably 50-400 liters of ready-to-use spray liquid are usually used per hectare of agricultural utilization area.

[0837] According to one embodiment, the user can mix the individual components or partially premixed components of the agrochemical composition of the present invention in a spray tank, for example, the components comprising the pyridyl ethers of formula (I) and, optionally, the active substances selected from groups B and / or C) and, if appropriate, further auxiliaries and additives.

[0838] In a further embodiment, the user can mix the components of the agrochemical composition according to the invention, for example the parts of a kit or the parts of a binary or ternary mixture, himself in a spray tank and, if appropriate, add further auxiliaries.

[0839] In another embodiment, the individual components or partially premixed components of the agrochemical composition of the invention, for example the components comprising pyridyl ethers of formula (I) and, optionally, active substances selected from groups B and / or C), can be applied jointly (for example after tank mixing) or sequentially.

[0840] The pyridyl ethers of formula (I) are suitable as herbicides. They are suitable directly, as appropriately formulated compositions (agrochemical compositions) or as herbicidal compositions in combination with at least one further compound selected from the group consisting of herbicidally active compounds B (component B) and safeners C (component C).

[0841] Pyridyl ethers of formula (I) or agrochemical compositions and / or herbicidal compositions comprising pyridyl ethers of formula (I) are very effective in controlling plant growth in non-crop areas, especially at high application rates. They act on broadleaf weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crops. This effect is mainly observed at low application rates.

[0842] The pyridyl ethers of formula (I) or the agrochemical compositions and / or herbicidal compositions comprising them are mainly applied to plants by spraying the leaves. For example, water can be used as a carrier here by conventional spraying techniques using a spraying liquid amount of about 100-1000 l / ha (e.g. 300-400 l / ha). The pyridyl ethers of formula (I) or the agrochemical compositions and / or herbicidal compositions comprising them can also be applied by low-volume or ultra-low-volume methods or in the form of microparticles.

[0843] The application of the pyridyl ethers of the formula (I) or of the agrochemical and / or herbicidal compositions comprising them can be carried out before, during and / or after, preferably during and / or after, the emergence of the undesired plants.

[0844] The pyridyl ethers of formula (I) or the agrochemical compositions and / or herbicidal compositions comprising them can be used before emergence, after emergence or before planting, or applied together with the seed of crops. It is also possible to apply the pyridyl ethers of formula (I) or the agrochemical compositions and / or herbicidal compositions comprising them by applying the seeds of crops pretreated with the pyridyl ethers of formula (I) or the agrochemical compositions and / or herbicidal compositions comprising them. If the active ingredient can not be well tolerated by some crops, then it is possible to use the application technology (afterwards guiding, the last tillage procedure) wherein by means of the spraying equipment spraying herbicidal compositions so that they do not contact the leaves of sensitive crops as far as possible, and the active ingredient reaches the leaves of the undesirable plants grown below or the exposed soil surface.

[0845] In another embodiment, the pyridyl ethers of formula (I) or the agrochemical compositions and / or herbicidal compositions comprising them can be applied by treating seeds. The treatment of seeds basically includes all procedures well known to those skilled in the art for agrochemical compositions and / or herbicidal compositions based on pyridyl ethers of formula (I) or prepared therefrom (seed dressing, seed coating, seed dusting, seed soaking, seed coating, seed multilayer coating, seed shelling, seed dripping and seed pelleting). The herbicidal composition can be applied diluted or undiluted at this time.

[0846] The term "seed" includes all types of seeds, such as corn, seeds, fruits, tubers, rice seedlings and similar forms. The preferred term seed here describes corn and seeds. The seeds used can be seeds of the above-mentioned useful plants, but can also be seeds of transgenic plants or plants obtained by conventional breeding methods.

[0847] When used in plant protection, the application rates of active substances without formulation auxiliaries, i.e. pyridyl ethers of the formula (I), component B and, if appropriate, component C, are, depending on the desired effect, 0.001 to 2 kg / ha, preferably 0.005 to 2 kg / ha, more preferably 0.05 to 1.5 kg / ha and in particular 0.1 to 1 kg / ha.

[0848] In a further embodiment of the invention, the application rates of pyridyl ethers of the formula (I), component B and, if appropriate, component C are 0.001 to 3 kg / ha, preferably 0.005 to 2.5 kg / ha and in particular 0.01 to 2 kg / ha of active substance (as).

[0849] In another preferred embodiment of the present invention, the application rate of the pyridyl ethers of formula (I) of the present invention (total amount of pyridyl ethers of formula (I)) is 0.1-3000 g / ha, preferably 1-1000 g / ha, depending on the control target, season, target plant and growth stage.

[0850] In another preferred embodiment of the present invention, the application rate of the pyridyl ethers of formula (I) is 0.1-5000 g / ha, preferably 0.5-2500 g / ha or 2.5-2000 g / ha.

[0851] In another preferred embodiment of the present invention, the application rate of the pyridyl ethers of formula (I) is 0.1-1000 g / ha, preferably 0.5-750 g / ha, more preferably 2.5-500 g / ha.

[0852] The desired application rate of the herbicidal compound B is usually 0.0005-2.5 kg / ha, preferably 0.005-2 kg / ha or 0.01-1.5 kg / ha as.

[0853] The required application rates of safener C are generally 0.0005 to 2.5 kg / ha, preferably 0.005 to 2 kg / ha or 0.01 to 1.5 kg / ha as.

[0854] In the treatment of plant propagation material such as seeds, for example by dusting, coating or impregnating seeds, the amount of active substance required is usually 0.1-1000 g, preferably 1-1000 g, more preferably 1-100 g, most preferably 5-100 g per 100 kg of plant propagation material (preferably seeds).

[0855] In a further embodiment of the invention, for the treatment of seed, the active substances, ie the pyridyl ethers of the formula (I), component B and, if appropriate, component C, are generally applied in amounts of from 0.001 to 10 kg per 100 kg of seed.

[0856] When used to protect materials or stored products, the amount of active substance applied depends on the type of application area and the desired effect. In material protection, the amount usually applied is 0.001g-2kg, preferably 0.005g-1kg active substance per cubic meter of treated material.

[0857] In the case of the herbicidal compositions according to the invention, it is immaterial whether the pyridyl ethers of the formula (I) and the further components B and / or components C are formulated and applied jointly or separately.

[0858] In the case of separate application, the order in which the application is carried out is not very important. It is only necessary that the pyridyl ethers of formula (I) and the other components B and / or components C are applied within a time frame that allows these active ingredients to act on the plants simultaneously, preferably within a time frame of up to 14 days, especially up to 7 days.

[0859] Depending on the method of application, the pyridyl ethers of the formula (I) or the agrochemical compositions and / or herbicidal compositions comprising them can additionally be used in numerous other crops for combating undesirable plants. Examples of suitable crops are as follows: onion (Allium cepa), pineapple (Ananas comosus), peanut (Arachis hypogaea), asparagus (Asparagus officinalis), oats (Avena sativa), sugar beet (Beta vulgaris spec. altissima), sugar beet (Beta vulgaris spec. rapa), rapeseed (Brassica napus var. napus), turnip (Brassica napus var. napobrassica), turnip (Brassica rapa var. silvestris), kale (Brassica oleracea), black mustard (Brassica nigra), tea (Camellia sinensis), safflower (Carthamus tinctorius), pecan (Caryaillinoinensis), lemon (Citrus limon), sweet orange (Citrus sinensis), small-fruit coffee (Coffea arabica) (Coffea canephora), large-fruit coffee (Coffea liberica), Cucumber (Cucumissativus), Bermuda grass (Cynodon dactylon), Carrot (Daucus carota), Oil palm (Elaeisguineensis), European strawberry (Fragaria vesca), Soybean (Glycine max), Upland cotton (Gossypiumhirsutum) (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Sunflower (Helianthus annuus), Hevea brasiliensis, Barley (Hordeumvulgare), Hops (Humulus lupulus), Sweet potato (Ipomoea batatas), Walnut (Juglans regia), Lentil (Lens culinaris), Flax (Linum usitatissimum), Tomato (Lycopersicon lycopersicum), Apple (Malus spec.), cassava (Manihot esculenta), alfalfa (Medicago sativa), banana (Musa spec.), tobacco (Nicotiana tabacum) (N. rustica), olive (Olea europaea), rice (Oryza sativa), golden bean (Phaseolus lunatus), bean (Phaseolus vulgaris), European spruce (Picea abies), pine (Pinus spec.), pistachio (Pistacia vera), Pisum sativum, European sweet cherry (Prunus avium), Prunus persica, pear (Pyrus communis), apricot (Prunus armeniaca), European sour cherry (Prunus cerasus), almond (Prunus dulcis) and European plum (Prunus domestica), Ribes sylvestre, castor (Ricinus communis), sugarcane (Saccharum officinarum), rye (Secale cereale), white mustard (Sinapis alba), potato (Solanumtuberosum), Sorghum bicolor (Sorghum vulgare), cocoa (Theobromacacao), red clover (Trifolium pratense), common wheat (Triticum aestivum), triticale (Triticale), durum wheat (Triticum durum), bean (Vicia faba), grape (Vitis vinifera), and maize (Zea mays).

[0860] Preferred crops are groundnut (Arachis hypogaea), sugar beet (Beta vulgaris spec. altissima), rapeseed (Brassica napus var. napus), kale (Brassica oleracea), lemon (Citrus limon), sweet orange (Citrus sinensis), Coffea arabica (Coffea canephora, Coffea liberica), bermudagrass (Cynodon dactylon), soybean (Glycine max), upland cotton (Gossypium hirsutum) (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), sunflower (Helianthus annuus), barley (Hordeum vulgare), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple (Malus spec.), alfalfa (Medicago sativa), tobacco (Nicotiana tabacum) (N. rustica), olive (Olea europaea), rice (Oryza sativa), golden bean (Phaseolus lunatus), bean (Phaseolus vulgaris), pistachio (Pistacia vera), Pisum sativum, almond (Prunus dulcis), sugarcane (Saccharum officinarum), rye (Secale cereale), potato (Solanum tuberosum), bicolor sorghum (Sorghum bicolor) (S. vulgare), triticale (Triticale), common wheat (Triticum aestivum), durum wheat (Triticum durum), bean (Vicia faba), grape (Vitis vinifera) and maize (Zea mays).

[0861] Particularly preferred crops are cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts or perennial crops.

[0862] The pyridyl ethers of formula (I) of the present invention or agricultural chemical compositions and / or herbicidal compositions comprising them can also be used in genetically modified plants. The term "genetically modified plants" should be understood as plants whose genetic material includes insertion sequences of non-natural DNA for the genome of the plant variety or presents deletions of natural DNA for the genome of the variety by using recombinant DNA technology, wherein the modification is not easily obtained by hybridization, mutation or natural recombination alone. Special genetically modified plants are usually plants whose genetic modifications are obtained by natural breeding or propagation methods from the hereditary plants whose genome is a genome directly processed by using recombinant DNA technology. One or more genes are usually integrated into the genetic material of the genetically modified plant to improve certain properties of the plant. Such genetic modifications also include, but are not limited to, targeted post-translational modifications of proteins, oligopeptides or polypeptides, for example, by introducing amino acid mutations that allow, reduce or promote glycosylation or polymer addition such as isoprenylation, acetylation or farnesylation or PEG structure moiety attachment.

[0863] Plants modified by breeding, mutagenesis or genetic engineering have been made tolerant, for example, by conventional breeding or genetic engineering methods, to the application of particular classes of herbicides, such as auxin herbicides, for example dicamba or 2,4-D; bleach herbicides, for example 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors, for example sulfonylureas or imidazolinones; enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, for example glyphosate; glutamine synthase inhibitors, for example glyphosate; glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i.e., bromoxynil or ioxynil) herbicides; in addition, plants have been genetically modified multiple times to tolerate multiple classes of herbicides, such as tolerance to both glyphosate and glufosinate or tolerance to both glyphosate and another class of herbicides selected from ALS inhibitors, HPPD inhibitors, auxin inhibitors or ACCase inhibitors. These herbicide tolerance technologies are described, for example, in Pest Management Science 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Science 316, 2007, 1185; and in the literature cited therein. Several cultivated plants have been made tolerant to herbicides by genetic mutation and conventional breeding methods, for example, tolerant to imidazolinones such as imazamox. Summer rapeseed (Canola, BASF SE, Germany) or tolerant to sulfonylureas, such as tribenuron Sunflower (DuPont, USA). Genetic engineering methods have been used to confer tolerance to cultivated plants such as soybean, cotton, corn, sugar beet and rapeseed to herbicides such as glyphosate, imidazolinones and glufosinate, some of which are under development or available under the brand or trade name (glyphosate tolerant, Monsanto, USA), (Imidazolinone resistant, BASF SE, Germany) and (Glufosinate-tolerant, Bayer CropScience, Germany) is commercially available.

[0864] Furthermore, plants are also included which are capable of synthesizing one or more insecticidal proteins, in particular those known from Bacillus bacteria, in particular Bacillus thuringiensis, by the use of recombinant DNA technology, such as delta-endotoxins, for example CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; asexual insecticidal proteins (VIP), for example VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of nematode-colonizing bacteria, for example Photorhabdus or Xenorhabdus; toxins produced by animals, such as scorpion toxins, spider toxins, wasp toxins or other insect-specific neurotoxins; toxins produced by fungi, for example Streptomyces; cetes) toxins; plant lectins, such as pea or barley lectins; lectins; protease inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cysteine ​​protease inhibitors or papain inhibitors; ribosome inactivating proteins (RIPs), such as ricin, maize-RIP, abrin, luffa seed protein, saporin or bryodin; steroid metabolizing enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitor or HMG-CoA reductase; ion channel blockers, such as sodium channel or calcium channel blockers; juvenile hormone esterase; helicokinin receptor; Synthetase, bibenzyl synthetase, chitinase or glucanase. In the context of the present invention, these insecticidal proteins or toxins are also specifically understood to include pretoxins, hybrid proteins, truncated or otherwise modified proteins. The feature of hybrid proteins is the novel combination of protein domains (for example, referring to WO 02 / 015701). Other examples of genetically modified plants of this type of toxin or capable of synthesizing these toxins are disclosed in EP-A 374 753, WO 93 / 007278, WO 95 / 34656, EP-A 427 529, EP-A 451 878, WO03 / 18810 and WO 03 / 52073. The method for producing these genetically modified plants is known to those skilled in the art and is for example disclosed in the above-mentioned publications. These insecticidal proteins contained in the genetically modified plants confer tolerance to all taxonomic arthropod pests, in particular beetles (Coeloptera), dipteran insects (Diptera) and moths (Lepidoptera) as well as nematodes (Nematoda). Genetically modified plants capable of synthesizing one or more insecticidal proteins are described, for example, in the above-mentioned publications, some of which are commercially available, for example (corn varieties that produce the toxin Cry1Ab), Plus (corn varieties producing toxins Cry1Ab and Cry3Bb1), (corn varieties that produce the toxin Cry9c), RW (a corn variety that produces the toxins Cry34Ab1, Cry35Ab1, and the enzyme phosphinothricin-N-acetyltransferase [PAT]); 33B (cotton variety producing the toxin Cry1Ac), I (cotton variety producing the toxin Cry1Ac), II (cotton varieties producing toxins Cry1Ac and Cry2Ab2); (cotton varieties that produce VIP toxins); (potato varieties that produce the toxin Cry3A); Bt11 (e.g. CB) and Bt176 of Syngenta Seeds SAS, France (a corn variety producing toxin Cry1Ab and PAT enzyme), MIR604 of Syngenta Seeds SAS, France (a corn variety producing a modified version of toxin Cry3A, see WO 03 / 018810), MON 863 of Monsanto Europe SA, Belgium (a corn variety producing toxin Cry3Bb1), IPC 531 of Monsanto Europe SA, Belgium (a cotton variety producing a modified version of toxin Cry1Ac) and 1507 of Pioneer Overseas Corporation, Belgium (a corn variety producing toxin Cry1F and PAT enzyme).

[0865] In addition, plants are also included that are able to synthesize one or more proteins that enhance resistance or tolerance to bacterial, viral or fungal pathogens by using recombinant DNA technology. Examples of such proteins are so-called "pathogenesis-related proteins" (PR proteins, see, for example, EP-A 392 225), plant disease resistance genes (e.g. potato varieties expressing resistance genes that act against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum) or T4 lysozyme (e.g. potato varieties that are able to synthesize these proteins that have enhanced resistance to bacteria such as Erwinia amylvora). Methods for producing these genetically modified plants are known to those skilled in the art and are disclosed, for example, in the above-mentioned publications.

[0866] Also included are plants that are capable of synthesizing one or more proteins through the use of recombinant DNA technology to increase yield (e.g., biomass production, grain yield, starch content, oil content, or protein content), tolerance to drought, salt, or other growth-limiting environmental factors, or tolerance to pests and fungal, bacterial, and viral pathogens.

[0867] In addition, plants are also included that contain altered amounts of ingredients or new ingredients, particularly to improve human or animal nutrition, by using recombinant DNA technology, such as oil crops that produce health-promoting long-chain ω-3 fatty acids or unsaturated ω-9 fatty acids (e.g. Rapeseed (DOW Agro Sciences, Canada).

[0868] Furthermore, plants are also included which contain altered or novel components by the use of recombinant DNA technology, in particular to improve raw material production, such as potatoes which produce increased amounts of amylopectin (e.g. potatoes, BASF SE, Germany).

[0869] Furthermore, it has been found that the pyridyl ethers of the formula (I) according to the invention or agrochemical compositions and / or herbicidal compositions comprising them are also suitable for defoliation and / or drying of plant parts, for which crops such as cotton, potatoes, rapeseed rape, sunflower, soybean or broad bean, in particular cotton, are suitable. In this regard, agrochemical compositions and / or herbicidal compositions for defoliation and / or defoliation of plants, methods for preparing these agrochemical compositions and / or herbicidal compositions and methods for defoliation and / or defoliation of plants using pyridyl ethers of the formula (I) have been found.

[0870] As desiccants, the pyridyl ethers of formula (I) are particularly suitable for drying the aerial parts of crops such as potatoes, rapeseed, sunflower and soybean and also cereals. This makes fully mechanized harvesting of these important crops possible.

[0871] Also of economic interest is the promotion of the harvest of citrus fruits, olives and other species and varieties of pome, drupes and nuts, which is made possible by concentrated cracking or reduced adhesion to the tree over a certain period of time. The same mechanism, i.e. the promotion of the production of abscission tissue between the fruit part or leaf part and the branch part of the plant, is also necessary for the controlled defoliation of useful plants, especially cotton.

[0872] Additionally, the shortened time interval between the maturation of individual cotton plants results in improved fiber quality after harvest.

[0873] Furthermore, it has been found that pyridyl ethers of the formula (I) or agrochemical compositions and / or herbicidal compositions comprising pyridyl ethers of the formula (I) are also very effective for controlling PPO-tolerant weeds.

[0874] Therefore, the present invention also provides a method for controlling the growth of PPO-tolerant weeds, comprising contacting such weeds, parts thereof, propagation materials thereof or a place of growth thereof with pyridyl ethers of formula (I), wherein the PPO-tolerant weeds are weeds tolerant to PPO-inhibiting herbicides other than pyridyl ethers of formula (I).

[0875] The present invention particularly relates to a method for controlling PPO-tolerant weeds in crops in which said PPO herbicide-tolerant weeds occur or may occur, comprising applying to the crops a pyridyl ether of formula (I).

[0876] As used herein, the terms "PPO inhibitor," "PPO inhibitor herbicide," "PPO-inhibiting herbicide," "protoporphyrinogen IX oxidase inhibitor herbicide," "protoporphyrinogen IX oxidase inhibiting herbicide," "protoporphyrinogen oxidase inhibitor herbicide," and "protoporphyrinogen oxidase inhibiting herbicide" are synonymous and refer to herbicides that inhibit the plant enzyme protoporphyrinogen oxidase.

[0877] As used herein, the terms "PPO inhibitor herbicide tolerant weeds", "PPO-inhibiting herbicide tolerant weeds", "PPO inhibitor tolerant weeds", "PPO tolerant weeds", "protoporphyrinogen IX oxidase inhibitor herbicide tolerant weeds", "protoporphyrinogen IX oxidase inhibiting herbicide tolerant weeds", "protoporphyrinogen oxidase inhibitor herbicide tolerant weeds" and "protoporphyrinogen oxidase inhibiting herbicide tolerant weeds" are synonymous and refer to plants that inherit, develop or acquire the ability, in response to treatment with a PPO-inhibiting herbicide at or above an appropriate application rate:

[0878] (1) survive a treatment if the treatment is lethal (i.e., destroyed) to the wild-type weed;

[0879] or

[0880] (2) Showing significant plant growth or vigorous growth after the treatment, if the treatment inhibits wild

[0881] Type of weed growth.

[0882] Effective weed control is defined as at least 70% suppression or destruction of weeds in the crop or at least 70% weed phytotoxicity measured 2 weeks after treatment.

[0883] Thus, PPO-tolerant weeds are weeds which cannot be controlled by applying PPO inhibitors other than pyridyl ethers of formula (I), whereas corresponding sensitive biotypes are controlled at the use rate.

[0884] Here, "uncontrolled" means weed control (herbicidal effect) measured in a visual assessment of <70% weed suppression or destruction 2 weeks after treatment; and "controlled" means weed control measured in a visual assessment of >90% weed suppression or destruction 2 weeks after treatment.

[0885] Preferably, PPO-tolerant weeds are weeds which cannot be controlled by application of PPO-inhibiting herbicides other than pyridyl ethers of formula (I) (ie weed control in a visual assessment measured at <70% weed inhibition or destruction 2 weeks after treatment).

[0886] It is also preferred that the PPO tolerant weeds are weeds which cannot be controlled by application of a PPO inhibiting herbicide selected from azadirachtin (ie weed control in a visual assessment measured at <70% weed suppression or destruction 2 weeks after treatment).

[0887] It is also preferred that the PPO tolerant weeds are weeds which are not controlled by application of a PPO inhibiting herbicide selected from the group consisting of azadirachtin, fomesafen and lactofen (ie weed control in a visual assessment measured as <70% weed suppression or destruction 2 weeks after treatment).

[0888] It is also preferred that the PPO tolerant weeds are weeds which are not controlled by application of a PPO inhibiting herbicide selected from fomesafen and lactofen (ie weed control in a visual assessment measured at <70% weed suppression or destruction 2 weeks after treatment).

[0889] It is also preferred that PPO-tolerant weeds are killed by application of acifluorfen, azopyralid, fluazifop-butyl, cypermethrin, cypermethrin, fluorine Weeds that were not controlled by the PPO-inhibiting herbicides of oxazolidinone, fomesafen, lactofen, oxadiazon, oxyfluorfen, fluazifop-butyl and sulfamethoxam (i.e., weed control in a visual assessment measured as <70% weed suppression or destruction 2 weeks after treatment).

[0890] It is also preferred that PPO-tolerant weeds are killed by applying a mixture selected from the group consisting of acifluorfen, fluazifop-butyl, cypermethrin, cypermethrin, fluorine Weeds that were not controlled by the PPO-inhibiting herbicides of oxazolidinone, fomesafen, lactofen, oxadiazon, oxyfluorfen, fluazifop-butyl and sulfamethoxam (i.e., weed control in a visual assessment measured as <70% weed suppression or destruction 2 weeks after treatment).

[0891] It is also preferred that PPO-tolerant weeds are weeds which cannot be controlled by PPO-inhibiting herbicides other than pyridyl ethers of the formula (I) at an application rate of 200 g / ha or less, particularly preferably 100 g / ha or less, especially preferably 50 to 200 g / ha, more preferably 50 to 100 g / ha (i.e. the weed control in a visual assessment is <70% weed inhibition or destruction measured 2 weeks after treatment), whereas corresponding sensitive biotypes are controlled at this application rate (i.e. the weed control in a visual assessment is >90% weed inhibition or destruction measured 2 weeks after treatment).

[0892] It is also preferred that PPO-tolerant weeds are weeds which are not controlled (i.e. the weed control in a visual assessment is <70% weed inhibition or destruction measured 2 weeks after treatment) by a PPO-inhibiting herbicide selected from the group consisting of azadirachtin, fomesafen and lactofen at an application rate of 200 g / ha or less, particularly preferably 100 g / ha or less, especially preferably 50 to 200 g / ha, more preferably 50 to 100 g / ha, whereas the corresponding sensitive biotypes are controlled at this application rate (i.e. the weed control in a visual assessment is >90% weed inhibition or destruction measured 2 weeks after treatment).

[0893] It is also preferred that PPO-tolerant weeds are weeds which cannot be controlled (i.e. the weed control in a visual assessment is <70% weed inhibition or destruction measured 2 weeks after treatment) by a PPO-inhibiting herbicide selected from fomesafen and lactofen at an application rate of 200 g / ha or less, particularly preferably 100 g / ha or less, especially preferably 50 to 200 g / ha, more preferably 50 to 100 g / ha, whereas the corresponding sensitive biotypes are controlled at this application rate (i.e. the weed control in a visual assessment is >90% weed inhibition or destruction measured 2 weeks after treatment).

[0894] It is also preferred that PPO-tolerant weeds are killed by application of acifluorfen, azopyralid, fluazifop, cypermethrin, fluorinated oxazolidinone, chlorpyrifos, chlorpyrifos, chlorpyrifos methyl, chlorpyrifos butyl ... Weeds that were not controlled by the PPO-inhibiting herbicides of oxazolidinone, fomesafen, lactofen, oxadiazon, oxyfluorfen, fluazifop-butyl and sulfamethoxam were not controlled (i.e., weed control was <70% weed inhibition or destruction measured in a visual assessment 2 weeks after treatment) while the corresponding sensitive biotypes were controlled at this use rate (i.e., weed control was >90% weed inhibition or destruction measured in a visual assessment 2 weeks after treatment).

[0895] It is also preferred that PPO-tolerant weeds are killed by application of a compound selected from the group consisting of acifluorfen, fluazifop-butyl, cypermethrin, cypermethrin, fluorinated weeds at an application rate of 200 g / ha or less, particularly preferably 100 g / ha or less, especially preferably 50-200 g / ha, more preferably 50-100 g / ha. Weeds that were not controlled by the PPO-inhibiting herbicides of oxazolidinone, fomesafen, lactofen, oxadiazon, oxyfluorfen, fluazifop-butyl and sulfamethoxam were not controlled (i.e., weed control was <70% weed inhibition or destruction measured in a visual assessment 2 weeks after treatment) while the corresponding sensitive biotypes were controlled at this use rate (i.e., weed control was >90% weed inhibition or destruction measured in a visual assessment 2 weeks after treatment).

[0896] Also preferred PPO-resistant weeds are those which are classified as "PPO-tolerant" and are listed accordingly according to Anonymous: List of herbicide resistant weeds by herbicide mode of action-weeds resistant to PPO-inhibitors (URL: http: / / www.weedscience.org / summary / MOA.aspx).

[0897] Particularly preferred PPO-tolerant weeds are selected from the genera Acalypha, Amaranthus, Ambrosia, Avena, Conyza, Descurainia, Euphorbia and Senecio; especially preferred are Amaranthus, Ambrosia and Senecio; more preferred are Amaranthus and Ambrosia.

[0898] Also particularly preferred are PPO-tolerant weeds selected from the group consisting of Asian iron amaranth (Acalypha australis), smooth hogweed (Amaranthus hybridus), long-horned amaranth (Amaranthus palmeri), redroot amaranth (Amaranthus retroflexus), tall / common waterhemp (Amaranthus tuberculatus, Amaranthus rudis or Amaranthus tamariscinus), ragweed (Ambrosia artemisiifolia), wild oats (Avena fatua), fleabane (Conyza ambigua), horsetail (Conyza canadensis), descurainia sophia (Descurainia sophia), wild poinsettia (Euphorbia heterophylla) and eastern groundsel (Senecio vernalis); especially preferred are smooth hogweed (Amaranthus viridis), Palmer amaranth, redroot amaranth (Amaranthus retroflexus), high / common waterhemp (Amaranthus sclerocarpa or Amaranthus tuberculosa), ragweed and wild poinsettia (Euphorbia microphylla); more preferred are high / common waterhemp (Amaranthus sclerocarpa, Amaranthus tuberculosa or Amaranthus tamariscinus) and ragweed.

[0899] Most PPO-tolerant weeds, especially biotypes of Amaranthus sclerotiorum, are tolerant due to a codon deletion in the nuclear-encoded gene PPX2L, which encodes a PPO enzyme that is dual-targeted to mitochondria and chloroplasts. This results in the loss of a glycine amino acid in position 210 (see, e.g., BG Young et al., Characterization of the response of PPO inhibitor-tolerant waterhemp (Amaranthus sclerotiorum) to soil-applied PPO-inhibiting herbicides, Weed Science 2015, 63, 511-521).

[0900] The second class of mutations, especially in tolerant biotypes of ragweed, was identified as mutations expressing the R98L change in the PPX2 enzyme (SLRousonelos, RM Lee, MS Moreira, MJ Van Gessel, PJ Tranel, Characterization of a ragweed population tolerant to ALS and PPO-inhibiting herbicides, Weed Science 60, 2012, 335-344).

[0901] Thus, preferred PPO tolerant weeds are weeds whose Protox enzymes are tolerant to the application of PPO inhibitors due to mutations expressed as ΔG210 or R98L changes of said Protox enzymes or equivalents of PPX2L or PPX2, respectively, especially expressed as ΔG210 or R98L changes of said Protox enzymes.

[0902] The preparation of the phenyluracils of the formula (I) is illustrated by the examples; however, the subject matter of the invention is not restricted to the examples given.

[0903] A. Preparation Example

[0904] Embodiment 1:

[0905] Ethyl 2-[2-[[3-chloro-6-[4-difluoromethyl-3-methyl-5-oxo-1,2,4-triazol-1-yl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetate

[0906]

[0907] Example 1 Step 1: (5-chloro-3,6-difluoro-2-pyridyl)hydrazine

[0908] To a solution of 0.5 g (2.98 mmol) 2,3,6-trifluoro-5-chloropyridine (CAS 2879-42-7) in 7 mL EtOH was added 0.23 g (2.98 mmol) hydrazine monohydrate at room temperature. The mixture was stirred at 60 ° C for 18 hours, cooled to room temperature and filtered. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 0.39 g (2.18 mmol, 73%) of the desired compound 1 Step 1.

[0909] 1H-NMR (CDCl3, ppm): 7.33 (dd, J=9.00Hz, J=6.63Hz, 1H); 6.05 (br.s, 1H); 3.84 (br.s., 2H).

[0910] [M+H]=180.0; Rt=0.548min.

[0911] Example 1 Step 2: (2E / Z)-2-[(5-chloro-3,6-difluoro-2-pyridyl)hydrazono]propanoic acid

[0912]

[0913] To a solution of 0.58 g (3.23 mmol) of compound 1 step 1 in 13 mL of EtOH was added 0.29 g (3.23 mmol) of pyruvic acid dropwise. The mixture was stirred at room temperature for 18 hours. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 0.63 g (2.53 mmol, 78%) of the desired compound 1 step 2.

[0914] [M+H]=249.9; Rt=0.833min.

[0915] Example 1, Step 3: 2-(5-chloro-3,6-difluoro-2-pyridyl)-5-methyl-4H-1,2,4-triazol-3-one

[0916]

[0917] To a solution of 3.4 g (13.6 mmol) of compound 1 step 2 in 45 mL of toluene was added 1.38 g (13.6 mmol) of triethylamine, and then 3.75 g (13.6 mmol) of diphenylphosphoryl azide was added dropwise at room temperature. The mixture was refluxed for 3 hours, cooled to room temperature and stirred for another 18 hours. The mixture was washed with saturated aqueous Na2CO3 solution. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 1.9 g (7.72 mmol, 57%) of the desired compound 1 step 3.

[0918] [M+H]=247.0; Rt=0.737min.

[0919] Example 1, Step 4: 2-(5-chloro-3,6-difluoro-2-pyridyl)-4-difluoromethyl-5-methyl-1,2,4-triazol-3-one

[0920]

[0921] To a solution of 28.0 g (113 mmol) of compound 1 step 3 in 455 mL of acetonitrile was added 17.3 g (125 mmol) of potassium carbonate, followed by 27.7 g (136 mmol) of ethyl bromodifluoroacetate at room temperature. The mixture was refluxed for 6 hours, cooled to room temperature and stirred for another 18 hours at room temperature. The solvent was removed under reduced pressure, ethyl acetate was added and the mixture was washed with water. The combined organic layers were dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 3.24 g (10.95 mmol, 10%) of the desired compound 1 step 4.

[0922] 1H-NMR (CDCl3, ppm): 7.82 (dd, J=7.46Hz, J=6.77Hz, 1H); 7.04 (t, J=57.94Hz, 1H); 2.50 (s, 3H).

[0923] [M+H]=297.0; Rt=1.005min.

[0924] Example 1, Step 5: Ethyl 2-[2-[[3-chloro-6-[4-difluoromethyl-3-methyl-5-oxo-1,2,4-triazol-1-yl]-5-fluoro-2-pyridyl]oxy]phenoxy]acetate

[0925]

[0926] To a solution of 2.8 g (9.47 mmol) of compound 1 step 4 in 38 mL of tetrahydrofuran was added 3.09 g (9.47 mmol) of cesium carbonate, followed by 1.86 g (9.47 mmol) of ethyl 2-(2-hydroxyphenoxy)acetate (CAS 99186-63-7). The mixture was refluxed for 96 hours. The mixture was filtered and the solvent was removed under reduced pressure. The crude mixture was then dissolved in 50 mL of EtOH, acidified to pH 3-4 by the addition of concentrated H2SO4, and stirred at room temperature for 18 hours. The solvent was removed under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (petroleum ether / ethyl acetate) on silica to give 3.20 g (6.77 mmol, 71%) of the desired compound 1.

[0927] 1H-NMR (CDCl3, ppm): 7.75 (d, J=7.77Hz, 1H); 7.23 (dd, J=7.91Hz, J=1.63Hz, 1 H); 7.19 (ddd, J=8.17Hz, J=7.57Hz, J=1.67Hz, 1H); 7.04 (dt, J=7.77Hz, J=7.7 7Hz, J=1.46Hz, 1H); 6.95 (t, J=58.13Hz, 1H); 6.93 (dd, J=8.18Hz, J=1.44Hz, 1 H); 4.57 (s, 2H); 4.15 (q, J=7.14Hz, 2H); 2.37 (s, 3H); 1.21 (t, J=7.14Hz, 3H).

[0928] [M+H]=473.1; Rt=1.226min.

[0929] Example 2: Ethyl 2-[2-[[3-carbamothioyl-5-fluoro-6-[4-methyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]-2-pyridinyl]oxy]phenoxy]acetate

[0930]

[0931] Example 2 Step 1: 2,5-difluoro-6-[4-methyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]pyridine-3-carbonitrile

[0932]

[0933] To a solution of 2.5 g (16.0 mmol) 4-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-one (CAS 51856-10-1) in 40 mL dimethyl sulfoxide was added 2.4 g (16.0 mmol) 2,5,6-trifluoropyridine-3-carbonitrile (CAS 870065-73-9) and 2.2 g (16.0 mmol) potassium carbonate. The mixture was stirred at 20°C for 16 hours, the mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 3.1 g (9.6 mmol, 60%) of the desired compound 2 Step 1.

[0934] 1H-NMR (CDCl3, ppm): 7.96-8.08 (m, 1H); 3.43-3.60 (m, 3H).

[0935] Example 2 Step 2: 5-Fluoro-2-(2-methoxyphenoxy)-6-[4-methyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]pyridine-3-carbonitrile

[0936]

[0937] To a solution of 1.1 g (3.6 mmol) of compound 2 step 1 in 20 mL of dimethyl sulfoxide were added 0.45 g (3.6 mmol) of 2-methoxyphenol (CAS 90-05-1) and 0.99 g (7.2 mmol) of potassium carbonate. The mixture was stirred at 50°C for 16 hours, the mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure to give the desired compound 2 step 2 (2.5 g), which was used in the next step without further purification. Example 2 step 3: 5-Fluoro-2-(2-hydroxyphenoxy)-6-[4-methyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]pyridine-3-carbonitrile

[0938]

[0939] To a solution of 1.8 g (4.4 mmol) of compound 2 step 2 in 30 mL of dichloromethane was added dropwise 3.3 g (13.2 mmol) of boron tribromide at 0°C, the mixture was stirred at 20°C for 16 hours, the mixture was poured into ice water, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to give the desired product 2 step 3 (1.9 g), which was used in the next step without further purification.

[0940] Example 2, Step 4: Ethyl 2-[2-[[3-cyano-5-fluoro-6-[4-methyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]-2-pyridinyl]oxy]phenoxy]acetate

[0941]

[0942] To a solution of 0.51 g (1.3 mmol) of compound 2, step 3 in 10 mL of acetonitrile was added 0.26 g (1.6 mmol) of ethyl 2-bromoacetate (CAS 105-36-2) and 0.36 g (2.6 mmol) of potassium carbonate. The mixture was stirred at 20° C. for 16 hours, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The crude product was purified by reverse phase preparative HPLC (acetonitrile / water, containing ammonium bicarbonate) to give 0.2 g (0.4 mmol, 32%) of the desired compound 2.

[0943] 1H-NMR (CDCl3, ppm): 7.95 (d, J=7.78Hz, 1H); 7.21-7.26 (m, 2H); 7.04-7.10 (m, 1 H); 6.94 (dd, J=8.16, 1.25Hz, 1H); 4.59 (s, 2H); 4.09-4.18 (m, 2H); 3.39 (s, 3H).

[0944] [M+H]=481.9; Rt=1.189min.

[0945] Example 3: Ethyl 2-[2-[[3-carbamoylthio-5-fluoro-6-[4-methyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]-2-pyridinyl]oxy]phenoxy]acetate

[0946]

[0947] At 15°C, hydrogen sulfide was bubbled through a solution of 0.2 g (0.4 mmol) of compound 2 step 4 (compound 2) in 10 mL of pyridine and 2 mL of triethylamine, and the mixture was then stirred at 15°C for 2 hours, the mixture was diluted with water, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure. The crude product was crystallized (from petroleum ether / methyl tert-butyl ether 10:1) to give 0.4 g (0.37 mmol, 93%) of the desired compound 3.

[0948] 1H-NMR (CDCl3, ppm): 9.41 (br s, 1H); 8.73 (d, J=9.54Hz, 1H); 8.17 (br s, 1H); 7.52 (dd, J=8.03, 1.51Hz, 1H); 7.19-7.26 (m, 1H); 7.06-7.14 (m, 1H); 6.93 (d, J= 8.16Hz, 1H); 4.59 (s, 2H); 4.22 (q, J=7.15Hz, 2H); 3.41 (s, 3H); 1.27 (t, J=7.15Hz, 3H).

[0949] [M+H]=515.9; Rt=1.159min.

[0950] Embodiment 4:

[0951] Ethyl 2-[2-[[3,5-dichloro-6-(3-oxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-2-yl)-2-pyridinyl]oxy]phenoxy]acetate

[0952]

[0953] Example 4 Step 1: 2-(3,5,6-trichloro-2-pyridyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0954]

[0955] To a solution of 8.5 g (61.1 mmol) of 5,6,7,8-tetrahydro-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one (CAS 118801-67-5) in 5 mL of DMF was added 13.15 g (61.1 mmol) of 2,3,5,6-tetrachloropyridine (CAS 2402-79-1) and 1.5 g (7.91 mmol) of potassium carbonate. The mixture was stirred at 20° C. for 17 hours and then at 100° C. for 17 hours, the mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 3.5 g (9.78 mmol, 16%) of the desired compound 4 Step 1.

[0956] 1H-NMR (CDCl3, ppm): 7.95-8.07 (m, 1H); 7.27 (d, J=2.51Hz, 1H); 3.64-3.74 (m, 2H); 2.76-2.84 (m, 2H), 1.90-2.09 (m, 6H).

[0957] Example 4 Step 2: 2-[3,5-dichloro-6-(2-methoxyphenoxy)-2-pyridinyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0958]

[0959] To a solution of 2.5 g (7.9 mmol) of compound 4 step 1 in 25 mL of DMF was added 1 g (7.9 mmol) of 2-methoxyphenol (CAS 90-05-1) and 1.65 g (11.9 mmol) of potassium carbonate. The mixture was stirred at 100° C. for 17 hours, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 3.2 g (7.9 mmol, 99%) of the desired compound 4 step 2.

[0960] 1H-NMR (CDCl3, ppm): 7.90 (s, 1H); 7.15-7.21 (m, 2H); 6.85-6.99 (m, 3H); 3.7 6 (s, 3H); 3.61 (t, J=6.06Hz, 2H); 2.68 (t, J=6.39Hz, 2H); 1.79-1.97 (m, 5H).

[0961] Example 4 Step 3: 2-[3,5-dichloro-6-(2-hydroxyphenoxy)-2-pyridinyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-3-one

[0962]

[0963] To a solution of 3.2 g (7.88 mmol) of compound 4 from step 2 in 35 mL of dichloromethane, 6.0 g (23.6 mmol) of boron tribromide was added dropwise at 0°C. The mixture was stirred at 20°C for 17 hours, poured into ice water, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to give the desired product 4 step 3 (2.5 g), which was used in the next step without further purification.

[0964] 1H-NMR (CDCl3, ppm): 7.92 (s, 1H); 7.22 (d, J=7.50Hz, 1H); 7.10-7.17 (m, 2H); 6.95-7.01 (m , 1H); 6.78-6.89 (m, 3H); 3.66 (t, J=6.06Hz, 2H); 2.73 (t, J=6.39Hz, 2H); 1.83-2.01 (m, 4H).

[0965] Example 4 Step 4: Ethyl 2-[2-[[3,5-dichloro-6-(3-oxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-2-yl)-2-pyridinyl]oxy]phenoxy]acetate

[0966]

[0967] To a solution of 1.0 g (2.5 mmol) of compound 4, step 3 in 10 mL of acetonitrile was added 0.852 g (5.1 mmol) of ethyl 2-bromoacetate (CAS 105-36-2) and 0.704 g (5.1 mmol) of potassium carbonate. The mixture was stirred at 20° C. for 17 hours. The solvent was removed under reduced pressure. The crude product was purified by reverse phase preparative HPLC (acetonitrile / water, containing trifluoroacetic acid) to give 0.35 g (0.4 mmol, 16%) of the desired compound 4.

[0968] 1H-NMR (CDCl3, ppm): 7.92 (s, 1H); 7.24 (dd, J=7.91, 1.51Hz, 1H); 7.17 (td, J=7.87, 1.57Hz, 1H); 7.01-7.06 (m, 1H); 6.92-6.96 (m, 1H); 4.59 ( s, 2H); 4.18 (q, J=7.15Hz, 2H); 3.61 (t, J=6.02Hz, 2H); 2.68 (t, J=6.40Hz, 2H); 1.89-1.97 (m, 2H); 1.82-1.89 (m, 2H); 1.23 (t, J=7.15Hz, 3H).

[0969] [M+H]=478.9; Rt=1.157min.

[0970] Example 5: 2-[2-[[6-(5-tert-butyl-2-oxo-1,3,4- oxadiazole-3-yl)-3,5-dichloro-2-pyridyl]oxy]phenoxy]ethyl acetate

[0971]

[0972] Example 5 Step 1: 5-tert-butyl-3-[3,5-dichloro-6-(2-methoxyphenoxy)-2-pyridinyl]-1,3,4- 2-oxadiazol-2-one

[0973]

[0974] To 4.5 g (14.0 mmol) of 5-tert-butyl-3-(3,5-dichloro-6-fluoro-2-pyridyl)-1,3,4- To a solution of oxadiazole-2-one (CAS 68617-97-0) in 50 mL of DMF were added 1.7 g (14.0 mmol) of 2-methoxyphenol (CAS 90-05-1) and 5.8 g (42.0 mmol) of potassium carbonate. The mixture was stirred at 80° C. for 17 hours, diluted with water and extracted with methyl tert-butyl ether. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 2.4 g (5.88 mmol, 42%) of the desired compound 5 Step 1.

[0975] 1H-NMR (CDCl3, ppm): 7.92 (s, 1H); 7.18-7.26 (m, 2H); 6.96-7.01 (m, 2H); 3.77 (s, 3H); 1.30 (s, 9H).

[0976] Example 5 Step 2: 5-tert-butyl-3-[3,5-dichloro-6-(2-hydroxyphenoxy)-2-pyridinyl]-1,3,4- 2-oxadiazol-2-one

[0977]

[0978] To a solution of 2.4 g (5.8 mmol) of compound 5 step 1 in 30 mL of dichloromethane was added dropwise 2.2 g (8.8 mmol) of boron tribromide at 0° C., the mixture was stirred at 20° C. for 17 hours, poured into ice water, and extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to give the desired product 5 step 2 (2.0 g), which was used in the next step without further purification.

[0979] 1H-NMR (CDCl3, ppm): 7.96-8.01 (m, 1H); 7.62-7.70 (m, 2H); 7.09-7.20 (m, 3H); 6.96-7.07 (m, 2H); 6.86-6.93 (m, 1H); 5.31 (s, 2H); 1.08 (s, 9H).

[0980] Example 5 Step 3: 2-[2-[[6-(5-tert-butyl-2-oxo-1,3,4- oxadiazole-3-yl)-3,5-dichloro-2-pyridyl]oxy]phenoxy]ethyl acetate

[0981]

[0982] To a solution of 2.0 g (5.0 mmol) of compound 5 step 2 in 20 mL of acetonitrile was added 1.69 g (10.0 mmol) of ethyl 2-bromoacetate (CAS 105-36-2) and 2.79 g (20.0 mmol) of potassium carbonate. The mixture was stirred at 20° C. for 17 hours, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 0.3 g (0.6 mmol, 12%) of the desired compound 5.

[0983] 1H-NMR (CDCl3, ppm): 7.96-8.01 (m, 1H); 7.62-7.70 (m, 2H); 7.09-7.20 (m, 3H); 6.96-7.07 (m, 2H); 6.86-6.93 (m, 1H); 5.31 (s, 2H); 1.08 (s, 9H).

[0984] [M+H]=482.0; Rt=1.387min.

[0985] Example 6: Ethyl 2-[2-[[3-chloro-6-[4-chloro-5-(difluoromethoxy)-1-methyl-pyrazol-3-yl]-5-fluoro-2-pyridyl]oxy]phenoxy]acetate

[0986]

[0987] Example 6 Step 1: 4-Chloro-5-(difluoromethoxy)-3-iodo-1-methylpyrazole

[0988]

[0989] To a solution of 5.2 g (20.56 mmol) of iodine in 25 mL of acetonitrile was added 2.12 g (20.56 mmol) of tert-butyl nitrite at 0°C under argon atmosphere. The mixture was stirred at 0°C for 1 hour, then 2.7 g of 4-chloro-5-(difluoromethoxy)-1-methyl-1H-pyrazol-3-amine (CAS 149978-51-8) was added at 0°C, the mixture was stirred at 20°C for 2 hours, the mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with aqueous Na2S2O3, dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 3.2 g (15.6 mmol, 76%) of the desired compound 6 Step 1.

[0990] Example 6 Step 2: Tributyl-[4-chloro-5-(difluoromethoxy)-1-methyl-pyrazol-3-yl]stannane

[0991]

[0992] To a solution of 2.2 g (7.15 mmol) of compound 6 step 1 in 40 mL of tetrahydrofuran was added 4.3 mL (8.6 mmol, 2 M in THF) of isopropylmagnesium chloride at -10°C under an argon atmosphere. The mixture was stirred at -10°C for 15 minutes, then 2.8 g of tributyltin chloride (CAS 1461-22-9) was slowly added at -10°C, the mixture was stirred at 20°C for 1.5 hours, the mixture was quenched with saturated NH4Cl aqueous solution, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 2.5 g (5.4 mmol, 75%) of the desired compound 6 step 2.

[0993] 1H-NMR (CDCl3, ppm): 6.82 (d, J=1.10Hz, 1H); 6.63 (d, J=1.32Hz, 1H); 6.45 (d, J=1. 32Hz, 1H); 3.77 (s, 3H); 1.48-1.65 (m, 6H); 1.10-1.39 (m, 17H); 0.80-0.96 (m, 16H).

[0994] Example 6 Step 3: 2-Bromo-5-chloro-3-fluoro-6-(2-methoxyphenoxy)pyridine

[0995]

[0996] To a solution of 7.7 g (107.8 mmol) of sodium azide in 120 mL of dimethyl sulfoxide at 0°C was added 18.0 g (118.6 mmol) of 3-chloro-2,5,6-trifluoropyridine (CAS 2879-42-7). The mixture was stirred at 20°C for 3 hours, and then a solution of 14.0 g (113.0 mmol) of 2-methoxyphenol (CAS 90-05-1) was added in portions to the above mixture at 0°C. The resulting mixture was stirred at 25°C for 16 hours, diluted with ice water, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure to give the desired product 6 Step 3, which was used in the next step without further purification.

[0997] Example 6 Step 4: 5-Chloro-3-fluoro-6-(2-methoxyphenoxy)pyridin-2-amine

[0998]

[0999] To a suspension of 18.0 g (61.1 mmol) of compound 6 step 3 and 35.0 g (537.0 mmol) of zinc in 400 mL of tetrahydrofuran, 350 mL of half-saturated NH4Cl aqueous solution was added dropwise at 0°C. The mixture was stirred at 20°C for 3 hours, filtered, and the filter cake was washed with ethyl acetate. Water was added to the filtrate, the mixture was extracted with ethyl acetate, the organic layer was dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 16.0 g (59.5 mmol, 97%) of the desired product 6 step 4.

[1000] Example 6 Step 5: 2-Bromo-5-chloro-3-fluoro-6-(2-methoxyphenoxy)pyridine

[1001]

[1002] To a solution of 7.0 g (26.1 mmol) of compound 6 step 4 in 70 mL of acetonitrile was added dropwise 5.8 g (26.1 mmol) of copper (II) bromide and 3.0 g (28.7 mmol) of tert-butyl nitrite at -15 ° C. The mixture was stirred at 20 ° C. for 2 hours, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 8.4 g (11.0 mmol, 42%) of the desired compound 6 step 5.

[1003] 1H-NMR (CDCl3, ppm): 7.57 (d, J=6.39Hz, 1H); 7.21-7.26 (m, 1H); 7.12-7.17 (m, 1H); 6.97-7.04 (m, 2H); 3.76 (s, 3H).

[1004] Example 6 Step 6: 2-[(6-bromo-3-chloro-5-fluoro-2-pyridyl)oxy]phenol

[1005]

[1006] To a solution of 6.4 g (19.2 mmol) of compound 6 step 5 in 20 mL of dichloromethane was added dropwise 7.2 g (28.8 mmol) of boron tribromide at 0°C. The mixture was stirred at 20°C for 1.5 hours. The mixture was poured into ice water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure to give the desired product 6 step 6 (5.3 g), which was used in the next step without further purification.

[1007] 1H-NMR (CDCl3, ppm): 7.62 (d, J=6.17Hz, 1H); 7.13-7.21 (m, 2H); 7.05-7.10 (m, 1H); 6.86-7.01 (m, 1H); 5.82 (br s, 1H); 4.13 (q, J=7.06Hz, 1H); 2.05 (s, 2H); 1.27 (t, J=7.06Hz, 2H).

[1008] Example 6, Step 7: Ethyl 2-[2-[(6-bromo-3-chloro-5-fluoro-2-pyridyl)oxy]phenoxy]acetate

[1009]

[1010] To a solution of 2.0 g (6.2 mmol) of compound 6 step 6 in 20 mL of acetonitrile was added dropwise 1.7 g (12.2 mmol) of potassium carbonate and 2.1 g (12.6 mmol) of ethyl 2-bromoacetate (CAS 105-36-2). The mixture was stirred at 20° C. for 17 hours, the mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 2.0 g (4.96 mmol, 80%) of the desired compound 6 step 7.

[1011] 1H-NMR (MeOD, ppm): 7.91 (d, J=6.78Hz, 1H); 7.14-7.27 (m, 2H); 7.04-7.09 (m, 2H); 4.58 (s, 2H); 4.15 (q, J=7.07Hz, 2H); 1.22 (t, J=7.09Hz, 3H).

[1012] Example 6, Step 8: Ethyl 2-[2-[[3-chloro-6-[4-chloro-5-(difluoromethoxy)-1-methyl-pyrazol-3-yl]-5-fluoro-2-pyridyl]oxy]phenoxy]acetate

[1013]

[1014] To a solution of 0.6 g (1.3 mmol) of compound 6, step 7, in 5 mL of dry dimethylformamide under argon atmosphere was added 0.05 g (0.07 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.5 g (1.3 mmol) of compound 5.2. The mixture was stirred at 80° C. for 3 hours. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The crude product was purified by reverse phase preparative HPLC (acetonitrile / water with trifluoroacetic acid) to give 0.2 g (0.35 mmol, 27%) of the desired compound 6.

[1015] 1H-NMR (CDCl3, ppm): 7.67 (d, J=8.78Hz, 1H); 7.24 (br d, J=7.91Hz, 1H); 7.17 (br t, J=7.59Hz, 1H); 7.01-7.08 (m, 1H); 6.93 (br d, J=8.16Hz, 1H); 6.78 (s, 1H); 6.60 (s, 1H); 6.42 (s, 1H); 4.53 (s, 2H); 4.16 (q, J=6.99Hz, 2H); 3.79 (s, 3H); 1.21 (t, J=7.09Hz, 3H).

[1016] [M+H]=506.9; Rt=1.301min.

[1017] Example 7: Ethyl 2-[[3-[[3-chloro-6-(3,5-dimethyl-2,4,6-trioxo-1,3,5-triazine-1-yl)-5-fluoro-2-pyridyl]oxy]acetate

[1018]

[1019] Example 7 Step 1: Ethyl 2-[[3-[(6-azido-3-chloro-5-fluoro-2-pyridinyl)oxy]-2-pyridinyl]oxy]acetate

[1020]

[1021] To a solution of 1.8 g (10.78 mmol) 3-chloro-2,5,6-trifluoropyridine (CAS 2879-42-7) in 20 mL dimethyl sulfoxide was added 0.77 g (11.8 mmol) sodium azide at 23°C. The mixture was stirred at 23°C for 3 hours. Then a suspension of 2.2 g (11.3 mmol) ethyl 2-[(3-hydroxy-2-pyridyl)oxy]acetate (CAS: 353292-81-6) and 7.0 g (21.5 mmol) cesium carbonate in 10 mL dimethyl sulfoxide was added in batches to the above mixture. The resulting mixture was stirred at 23°C for 15 hours, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and the solvent removed under reduced pressure to give the desired product 7 Step 1, which was used in the next step without further purification.

[1022] [M+H]=367.9; Rt=1.276min.

[1023] Example 7 Step 2: Ethyl 2-[[3-[(6-amino-3-chloro-5-fluoro-2-pyridinyl)oxy]-2-pyridinyl]oxy]acetate

[1024]

[1025] To a suspension of 4.8 g (13.0 mmol) of compound 7 step 1 and 4.3 g (66.0 mmol) of zinc in 100 mL of tetrahydrofuran was added dropwise 50 mL of half-saturated NH4Cl aqueous solution at 0°C. The mixture was stirred at 23°C for 5 hours, filtered, and the filter cake was washed with ethyl acetate. 200 mL of water was added to the filtrate, the mixture was extracted with ethyl acetate, the organic layer was dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 2.7 g (8.0 mmol, 61%) of the desired product 7 step 2.

[1026] 1H-NMR (CDCl3, ppm): 7.9 (dd, J=4.89Hz, J=1.51Hz, 1H); 7.4 (d, J=7.39Hz, 1H); 7.3 (d, J=9.06Hz, 1H); 6 .9 (dd, J=7.65Hz, J=4.89Hz, 1H); 4.9 (s, 2H); 4.5 (s, 2H); 4.2 (q, J=7.15Hz, 2H); 1.25 (t, J=7.15Hz, 3H).

[1027] [M+H]=428.1; Rt=1.332min.

[1028] Example 7 Step 3: Ethyl 2-[[3-[[3-chloro-6-(3,5-dimethyl-2,4,6-trioxo-1,3,5-triazine-1-yl)-5-fluoro-2-pyridyl]oxy]acetate

[1029]

[1030] To a solution of 1.0 g (3.1 mmol) of compound 7 step 2 in 10 mL of ethyl acetate was added 1.5 g (9.2 mmol) of carbonyldiimidazole and 0.9 g (9.6 mmol) of triethylamine. The mixture was stirred at 65° C. for 2 hours, and then 0.27 g (3.1 mmol) of N,N-dimethylurea was added. The mixture was stirred at 65° C. for another 17 hours, the mixture was diluted with ice water, the pH was adjusted to 7 with 6N HCl, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 0.25 g (0.5 mmol, 17%) of the desired compound 7.

[1031] 1H-NMR (CDCl3, ppm): 7.97 (dd, J=5.02, 1.51Hz, 1H); 7.77 (d, J=7.15Hz, 1H); 7.49 (dd, J=7.65, 1.63Hz, 1H) ; 6.96 (dd, J=7.72, 4.96Hz, 1H); 4.78 (s, 2H); 4.19 (q, J=7.15Hz, 2H), 3.34 (s, 6H); 1.25 (t, J=7.09Hz, 3H).

[1032] [M+H]=482.0; Rt=1.137min.

[1033] Example 8: Ethyl 2-[[3-[[3-chloro-5-fluoro-6-[5-methyl-6-oxo-4-(trifluoromethyl)pyridazin-1-yl]-2-pyridinyl]oxy]acetate

[1034]

[1035] To a solution of 2.0 g (6.1 mmol) of 2-(5-chloro-3,6-difluoro-2-pyridyl)-4-methyl-5-(trifluoromethyl)pyridazin-3-one (CAS 1114184-80-3) in 20 mL of acetonitrile, 1.3 g (6.5 mmol) of ethyl 2-[(3-hydroxy-2-pyridyl)oxy]acetate (CAS: 353292-81-6) and 4.0 g (12.3 mmol) of cesium carbonate were added. The mixture was stirred at 20° C. for 17 hours. The solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (petroleum ether / ethyl acetate) to give 0.3 g (0.6 mmol, 10%) of the desired compound 8.

[1036] 1H-NMR (CDCl3, ppm): 7.97 (dd, J=4.96, 1.65Hz, 1H); 7.91 (s, 1H); 7.78 (d, J=7.50Hz, 1H); 7.51 (dd, J=7.72, 1.54Hz, 1H); 6.96 (dd, J=7.72, 4.85Hz, 1H); 4.81 (s, 2H); 4.17 (q, J=7.06Hz, 2H); 2.35-2.38 (m, 3H); 1.23 (t, J=7.06Hz, 3H).

[1037] [M+H]=503.0; Rt=1.284min.

[1038] The compounds listed in Tables 1-9 below can be prepared similarly to the above examples:

[1039]

[1040] Table 1

[1041] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> m / z[M+H] <![CDATA[R t [min]]]> 9 F F 457 1.132 10 Cl Cl 489 1.218 11 H Cl 455 1.200 12 F CN 464 1.142

[1042]

[1043] Table 2

[1044] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> m / z[M+H] <![CDATA[R t [min]]]> 13 F Cl 474 1.175 14 F F 458 1.063 15 Cl Cl 490 1.187 16 H Cl 456 1.173 17 F CN 465 1.108

[1045]

[1046] Table 3

[1047] Example No. <![CDATA[R 2 ]]> <![CDATA[A 1 ]]> m / z[M+H] <![CDATA[R t [min]]]> 18 CN S 497.9 1.262

[1048]

[1049] Table 4

[1050] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> m / z[M+H] <![CDATA[R t [min]]]> 19 F Cl 505.9 1.327

[1051]

[1052] Table 5

[1053] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> m / z[M+H] <![CDATA[R t [min]]]> 20 F Cl 497.9 1.276

[1054]

[1055] Table 6

[1056] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> m / z[M+H] <![CDATA[R t [min]]]> 21 F Cl 501.9 1.312

[1057]

[1058] Table 7

[1059] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> m / z[M+H] <![CDATA[R t [min]]]> 22 F Cl 534.4 1.372 23 H Cl 516.1 1.270

[1060]

[1061] Table 8

[1062] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> m / z[M+H] <![CDATA[R t [min]]]> 24 F Cl 501.9 1.197

[1063]

[1064] Table 9

[1065] Example No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> m / z[M+H] <![CDATA[R t [min]]]> 25 F Cl 502.9 1.167

[1066] Example 26: 2-[2-[[3-Chloro-5-fluoro-6-(5-isopropylidene-2,4-dioxo- [(2-pyridyl)oxy]phenoxy]ethyl acetate

[1067]

[1068] Example 26 Step 1: Ethyl 2-[2-[(6-amino-3-chloro-5-fluoro-2-pyridyl)oxy]phenoxy]acetate

[1069]

[1070] To a solution of 40 g (0.24 mol) 3-chloro-2,5,6-trifluoropyridine (CAS 2879-42-7) in 400 mL dimethyl sulfoxide was added 17 g (0.26 mol) sodium azide at 23°C. The mixture was stirred at 23°C for 16 hours, and then a suspension of 49 g (0.25 mol) ethyl 2-(2-hydroxyphenoxy)acetate (CAS: 99186-63-7) and 155 g (0.48 mol) cesium carbonate in 100 mL dimethyl sulfoxide was added to the above mixture in batches. The resulting mixture was stirred at 23°C for 15 hours, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to give the desired product 26 Step 1, which was used in the next step without further purification.

[1071] [M+H]=367.0; Rt=1.276min.

[1072] Example 26 Step 2: Ethyl 2-[2-[(6-amino-3-chloro-5-fluoro-2-pyridyl)oxy]phenoxy]acetate

[1073]

[1074] To a suspension of 34 g (93.0 mmol) of compound 26 step 1 and 15.1 g (232.0 mmol) of zinc in 190 mL of tetrahydrofuran was added dropwise 150 mL of half-saturated NH4Cl aqueous solution at 0°C. The mixture was stirred at 23°C for 15 hours, filtered, and the filter cake was washed with ethyl acetate. 200 mL of water was added to the filtrate, the mixture was extracted with ethyl acetate, the organic layer was dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure to obtain the desired product 26 step 2, which was used in the next step without further purification.

[1075] 1H-NMR (CDCl3, ppm): 7.34 (d, J=9.0Hz, 1H), 7.18–7.09 (m, 2H), 7.06–6.99 (m, 1H), 6.95 (dd, J=8.1, 1.5Hz, 1H), 4.57 (s, 2H), 4.20 (q, J=7.1Hz, 2H), 3.97 (br, 2H), 1.25 (t, J=7.1Hz, 3H).

[1076] [M+H]=341.1; Rt=1.123min.

[1077] Example 26 Step 3: 2-[2-[[3-Chloro-5-fluoro-6-(5-isopropylidene-2,4-dioxo- [(2-pyridyl)oxy]phenoxy]ethyl acetate

[1078]

[1079] To a solution of 250 mg (0.73 mmol) of compound 26 step 2 in 8 mL of acetonitrile was added 238 mg (1.47 mmol) of 1,1-carbonyldiimidazole and 107 μL (0.77 mmol) of triethylamine. The mixture was stirred at 65 ° C for 1 hour, and then 106 mg (0.73 mmol) of 2-hydroxy-3-methylbut-3-enoic acid ethyl ester was added. The mixture was stirred at 80 ° C for another 17 hours. The volatiles were removed under reduced pressure. The crude product was purified by column chromatography on silica (cyclohexane / ethyl acetate) to give 97 mg (0.21 mmol, 28%) of the desired product 26.

[1080] 1H-NMR (CDCl3, ppm): 7.77 (d, J=7.3Hz, 1H), 7.23-7.15 (m, 2H), 7.03 (td, J=7.8, 1.5Hz, 1H), 6.88 (dd, J =8.1, 1.5Hz, 1H), 4.53 (s, 2H), 4.16 (q, J = 7.1Hz, 2H), 2.21 (s, 3H), 1.98 (s, 3H), 1.22 (t, J = 7.1Hz, 3H).

[1081] [M+H]=464.9; Rt=1.288.

[1082] Example 27: Ethyl 2-[2-[[3-chloro-6-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-5-fluoro-2-pyridyl]oxy]phenoxy]acetate

[1083]

[1084] Example 27 Step 1: 2-[5-chloro-3-fluoro-6-(2-methoxyphenoxy)-2-pyridinyl]-4,5,6,7-tetrahydroisoindole-1,3-dione

[1085]

[1086] To a solution of 1.0 g (3.7 mmol) of compound 6 step 4 in 30 mL of toluene was added 850 mg (5.6 mmol) of 3,4,5,6-tetrahydrophthalic anhydride (CAS 2426-02-0) and 1.0 g (5.6 mmol) of p-toluenesulfonic acid monohydrate (CAS 6192-52-5). The mixture was stirred at 100° C. for 16 hours. The reaction mixture was filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (cyclohexane / ethyl acetate) to give 715 mg (1.7 mmol, 48%) of the desired product 27 step 1.

[1087] [M+H]=403.0; Rt=1.284.

[1088] Example 27 Step 2: 2-[5-chloro-3-fluoro-6-(2-hydroxyphenoxy)-2-pyridinyl]-4,5,6,7-tetrahydroisoindole-1,3-dione

[1089]

[1090] To a solution of 660 mg (1.6 mmol) of compound 27 step 1 in 12 mL of dichloromethane was added 820 mg (3.3 mmol) of boron tribromide dropwise at -60°C. The mixture was stirred at 20°C for 15 hours. The mixture was poured into ice water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure to give the desired product 27 step 2 (630 mg), which was used in the next step without further purification.

[1091] [M+H]=389.0; Rt=1.165.

[1092] Example 27 Step 3: Ethyl 2-[2-[[3-chloro-6-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-5-fluoro-2-pyridyl]oxy]phenoxy]acetate

[1093]

[1094] To a solution of 630 mg (1.6 mmol) of compound 27 step 2 in 10 mL of dimethylformamide was added 440 mg (3.2 mmol) of potassium carbonate and 0.21 mL (1.9 mmol) of ethyl 2-bromoacetate (CAS 105-36-2). The mixture was stirred at 23° C. for 15 hours. The mixture was diluted with water and extracted with methyl tert-butyl ether. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica (cyclohexane / ethyl acetate) to give 382 mg (0.8 mmol, 50%) of the desired compound 27.

[1095] [M+H]=475.0; Rt=1.292.

[1096] 1H-NMR (CDCl3, ppm): 7.71 (d, J=7.4Hz, 1H), 7.21 (dd, J=7.8, 1.6Hz, 1H), 7.16 (td, J=7.8, 1.6Hz, 1H), 7.02 (td, J=7.7, 1.4Hz, 1H) , 6.90 (dd, J=8.1, 1.4Hz, 1H), 4.57 (s, 2H), 4.17 (q, J=7.2Hz, 2H), 2.38–2.29 (m, 4H), 1.76 (p, J=3.0Hz, 4H), 1.22 (t, J=7.2Hz, 3H).

[1097] B. Application Examples

[1098] The herbicidal activity of the pyridyl ethers of formula (I) was demonstrated by the following greenhouse test:

[1099] The culture containers used were plastic pots containing loamy sand containing about 3.0% humus as a substrate. The seeds of the test plants were sown individually for each variety.

[1100] For the pre-emergence treatment, the active ingredient suspended or emulsified in water is applied directly after sowing with the aid of a fine distribution nozzle. The containers are gently irrigated to promote germination and growth and then covered with a transparent plastic cover until the plants have rooted. This covering leads to uniform germination of the test plants, unless this is damaged by the active ingredient.

[1101] For the post-emergence treatment, the test plants are first grown to a height of 3-15 cm, depending on the plant habit, and only then treated with the active ingredient suspended or emulsified in water. For this purpose, the test plants are sown directly and grown in the same container, or they are first grown individually as seedlings and transplanted into the test containers a few days before the treatment.

[1102] Depending on the variety, the plants were kept at 10-25°C or 20-35°C, respectively.

[1103] The test period was 2-4 weeks, during which time the plants were cared for and their response to the treatments was evaluated.

[1104] Evaluation was performed using a scale of 0 to 100. 100 means that no plants emerged or at least the above-ground part was completely damaged, while 0 means no damage or normal growth. Good herbicidal activity was assigned a score of at least 70 and very good herbicidal activity was assigned a score of at least 85.

[1105] The plants used in the greenhouse experiments were of the following species:

[1106] Bayer Code scientific name ALOMY Alopecurus myosuroides AMARE Amaranthus retroflexus AVEFA Wild Oats (Avena fatua) CHEAL Chenopodium album ECHCG Echinocloa crus-galli POLCO Polygonum convolvulus SETVI Setaria viridis

[1107] At an application rate of 16 g / ha, compounds (Examples) 1, 8, 10, 12, 13, 15, 17, 19, 20, 22, 24 and 25 applied by the post-emergence method showed very good herbicidal activity against AMARE, CHEAL, ECHCG and SETVI.

[1108] At an application rate of 16 g / ha, compound (Example) 2 applied by the post-emergence method showed very good herbicidal activity against AMARE, ECHCG and SETVI.

[1109] At an application rate of 16 g / ha, compounds 3, 4, 7 applied by the post-emergence method (Examples) showed good herbicidal activity against AMARE.

[1110] At an application rate of 16 g / ha, compound (Example) 5 applied by the post-emergence method showed very good herbicidal activity against AMARE and CHEAL.

[1111] At an application rate of 16 g / ha, compounds 6, 21 applied by the post-emergence method (Example) showed very good herbicidal activity against AMARE, CHEAL, SETVI and POLCO.

[1112] At an application rate of 16 g / ha, compound (Example) 9 applied by the post-emergence method showed good herbicidal activity against CHEAL, ECHCG and SETVI.

[1113] At an application rate of 16 g / ha, compound 11 applied by the post-emergence method showed very good herbicidal activity against CHEAL and good herbicidal activity against POLCO.

[1114] At an application rate of 16 g / ha, compound 14 applied by the post-emergence method (Example) showed very good herbicidal activity against SETVI.

[1115] At an application rate of 16 g / ha, compound (Example) 16 applied by the post-emergence method showed very good herbicidal activity against AMARE, CHEAL and POLCO.

[1116] At an application rate of 16 g / ha, compound 18 applied by the post-emergence method (Example) showed very good herbicidal activity against AMARE and good herbicidal activity against SETVI.

[1117] At an application rate of 16 g / ha, compound (Example) 26 applied by the post-emergence method showed very good herbicidal activity against AMARE, CHEAL, POLCO and SETVI.

[1118] At an application rate of 16 g / ha, compound (Example) 27 applied by the post-emergence method showed very good herbicidal activity against AMARE, CHEAL, ECHCG, POLCO and SETVI.

[1119] Table 10: Comparison of herbicidal activity of the following compounds:

[1120] Embodiment 28 of the present invention

[1121]

[1122] (=compound of formula (I), wherein R 1 =F; R 2 =Cl; R 3 , R 4 =H; R 5 =OR 6 , R 6 =CH3; n=1; Q, W, X=O; Y=Y 55 , R 17 =CF3, R 18 =CH3, R 28 =H, A 1 =O; and Z = Z-3, R a , R b , R d and R e =H)

[1123] and Compound A2-11 known from JP 2001 / 27086

[1124]

[1125] Post-emergence control (greenhouse) 7 days after treatment:

[1126]

[1127]

[1128]

[1129]

[1130]

[1131] The data clearly show that the compounds of formula (I) according to the invention have superior herbicidal activity over the compounds known from the prior art.

[1132] Replacement of the central benzene ring by a pyridine ring leads to a much better herbicidal activity than achieved by the compounds known from JP 2001 / 270867.

Claims

1. Pyridyl ethers of formula (I) or agriculturally acceptable salts thereof: The variables have the following meanings: R 1 is H or halogen; R 2 is H, halogen, CN or C(=S)NH2; R 3 is H; R 4 is H; R 5 OR 6 ,in R 6 is hydrogen or C1-C6 alkyl; n is 1; Q is O; W is O; X is O; Y is selected from Y 2 , Y 20 , Y 31 , Y 38 , Y 55 , Y 65 , Y 66 , Y 67 or Y 68 Heterocyclic ring: in A 1 , A 2 , A 3 is oxygen or sulfur; R 12 , R 13 , R 17 and R 18 is hydrogen, C1-C6 alkyl or C1-C6 haloalkyl; or R 12 and R 13 Together with the atoms to which they are attached, they form a 6-membered ring, which is saturated or partially unsaturated; R 21 , R 22 , R 23 , R 24 is C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 haloalkoxy; or R 21 and R 22 Together with the atoms to which they are attached, they form a 6-membered ring, which is saturated or partially unsaturated; R 26 and R 27 is a C1-C6 alkyl group; R 28 is hydrogen, halogen or C1-C6 alkyl; and R 35 and R 36 is a C1-C6 alkyl group; Z is Z-1 or Z-7: in * indicates the connection point between Z and X; ** indicates the point of connection between Z and Q; and R a , R b , R c and R d For H.

2. Pyridyl ethers of formula (I) according to claim 1, wherein R 1 is H or F, and R 2 is F, Cl or CN.

3. Pyridyl ethers of formula (I) according to claim 1 or 2, wherein Y is selected from Y 2 , Y 20 , Y 31 , Y 38 , Y 67 or Y 68 .

4. Pyridyl ethers of formula (I) according to claim 1 or 2, wherein Y is selected from Y 2 , Y 20 or Y 67 .

5. A process for preparing pyridyl ethers of formula (I) as defined in claim 1, wherein a pyridine of formula (II): Where R 1 , R 2 and Y as defined in claim 1; and L 1 is halogen, C1-C6 alkylsulfonate or arylsulfonate; React with a compound of formula (III) in the presence of a base: Where R 3 , R 4 , R 5 , n, Q, W, X and Z are as defined in claim 1.

6. A herbicidal composition comprising a herbicidally active amount of at least one pyridyl ether of the formula (I) as claimed in any of claims 1 to 4 and at least one inert liquid and / or solid carrier and, if appropriate, at least one surface-active substance.

7. A process for preparing a herbicidally active composition, which comprises mixing a herbicidally active amount of at least one pyridyl ether of the formula (I) as claimed in any one of claims 1 to 4 with at least one inert liquid and / or solid carrier and, if desired, at least one surface-active substance.

8. A method for controlling unwanted vegetation, which comprises allowing a herbicidally active amount of at least one pyridyl ether of the formula (I) as claimed in any of claims 1 to 4 to act on plants, their environment or seeds.

9. Use of a pyridyl ether of the formula (I) as claimed in any one of claims 1 to 4 as a herbicide.

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