BR112020008053B1 - PYRIDIL ETHERS, PROCESS FOR PREPARING PYRIDIL ETHERS, HERBICIDAL COMPOSITION, PROCESS FOR PREPARING ACTIVE COMPOSITIONS, METHOD FOR CONTROLLING UNWANTED VEGETATION AND USE OF PYRIDIL ETHERS - Google Patents

Abstract

The present invention relates to pyridyl ethers of formula (I): or their salts or derivatives acceptable for agricultural use, in which the variables are defined in accordance with the specification, processes and intermediates for preparing the pyridyl ethers of formula (I ), compositions comprising them and their use as herbicides, i.e. to control weeds and also a method of controlling unwanted vegetation comprising maintaining a herbicide-effective quantity of at least one pyridyl ether of formula (I) in action about plants, their seeds and/or their habitat.

Description

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

[002] WO 88/01133 and WO 98/41093 describe structurally similar compounds that contain a central phenyl ring, wherein the compounds according to the present invention are characterized by a central pyridyl ring.

[003] The herbicidal properties of these known compounds in relation to weeds, however, are not always completely satisfactory.

[004] It is, therefore, the object of the present invention to provide pyridyl ethers of formula (I) that have improved herbicidal action. In particular, pyridyl ethers of formula (I) that have high herbicidal activity, particularly even at low application rates, and that are sufficiently compatible with producing plants for commercial use, must be provided.

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

[006] Consequently, the present invention provides pyridyl ethers of formula (I): wherein the substituents have the following meanings: - R1 is H or halogen; - R2 is H, halogen, CN, NO2, NH2, CF3 or C(=S)NH2; - R3 is H, halogen, CN, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, (C1-C3 alkyl)amino, dialkyl(C1-C3)amino, C1-C3 alkoxy C1-C3 alkyl or C1-C3 alkoxycarbonyl; - R4 is H, halogen, C1-C3 alkyl or C1-C3 alkoxy; - R5 is OR6, SR6, NR7R8, NR6OR6, NR6S(O)2R7 or NR6S(O)2NR7R8, where - R6 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, haloalkoxy C1-C6 alkyl C1-C6, alkenyloxy C3-C6 alkyl C1-C6, haloalkenyloxy C3-C6 alkyl C1-C6, alkenyloxy C3-C6 alkoxy C1-C6 alkyl, alkylthio C1-C6 alkyl C1-C6, alkylsulfinyl C1 -C6 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, C3-C6 alkynyloxycarbonyl C1-C6 alkyl, amino, (C1-C6 alkyl)amino, di(C1-C6 alkyl)amino, (C1-C6 alkylcarbonyl)amino, C1-C6 aminoalkyl, (C1-C6 alkyl)aminoalkyl C1-C6, di(C1-C6 alkyl)C1-C6 aminoalkyl, C1-C6 aminocarbonylalkyl, (C1-C6 alkyl)aminocarbonylC1-C6 alkyl and di(C1-C6 alkyl)aminocarbonylC1-C6 alkyl; - N=CR9R10, where R9 and R10, independently of each other, are H, C1-C4 alkyl or phenyl; - C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C6 heterocyclyl, C3-C6 heterocyclyl, C1-C6 alkyl, phenyl, C1-C4 phenylalkyl or 5- or 6-membered heteroaryl; wherein each cycloalkyl, heterocyclyl, phenyl or heteroaryl ring can be replaced by one to four substituents selected from R13 or 3 to 7 membered carbocycle; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of: -N(R9)-, -N=N-, -C(=O)-, - O- and -S-; and wherein the carbocycle is optionally substituted by one to four substituents selected from R11; wherein R11 is halogen, NO2, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 alkoxycarbonyl; - R7 and R8, independently of each other, are R6 or together they form a carbocycle with 3 to 7 members; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of -N(R9)-, -N=N-, -C(=O)-, -O - and -S-; and - m that the carbocycle is optionally substituted by one to four substituents selected from R11; - n is 1 to 3; - Q is O, S, SO, SO2, NH or (C1-C3 alkyl)N; - W is O or S; - X is O or S; - Y is a heterocycle selected from the group consisting of Y1 to Y76, preferably Y1 to Y75: where - A1, A2 and A3 are oxygen or sulfur; - A4 is oxygen, sulfur, SO or SO2; - R12, R13, R14, R15, R16, R17 and R18 are hydrogen, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, C1-C6 haloalkoxy, alkenyl C2-C6, C2-C6 haloalkenyl, C2C6 alkenyloxy, C3-C6 alkynyl, C3-C6 alkynyloxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkoxysulfonyl, C1-C6 alkylsulfonyloxy, amino, alkylamino C1-C6 or di(C1-C6 alkyl)amino; or - R12 and R13, together with the atoms to which they are bonded, form a cycle with three to six members, which is saturated, partially unsaturated or aromatic and may comprise, in addition to carbon atoms, one to four nitrogen atoms, one or two atoms of oxygen, one or two atoms of sulfur, one to three atoms of nitrogen and one atom of oxygen, one to three atoms of nitrogen and one atom of sulfur or one atom of sulfur and one atom of oxygen and, of part thereof may be totally or partially halogenated and/or substituted by one to three radicals from the group consisting of C1-C6 alkyl and C1-C6 alkoxy; - R19, R20, R21, R22, R23 and R24 are hydrogen, cyano, hydroxy, C1-C6 alkyl, C1-C6 cyanoalkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, haloalkoxy C1-C6, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkenyloxy, C3-C6 alkynyl, C3-C6 alkynyloxy, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 phenylalkyl, amino, C1-C6 alkylamino or di(C1-C6 alkyl)amino; or - R21 and R22, together with the atoms to which they are bonded, form a three- to six-membered cycle, which is saturated, partially unsaturated or aromatic and may comprise, in addition to carbon atoms, one to four nitrogen atoms, one or two atoms of oxygen, one or two atoms of sulfur, one to three atoms of nitrogen and one atom of oxygen, one to three atoms of nitrogen and one atom of sulfur or one atom of sulfur and one atom of oxygen and, of part thereof may be totally or partially halogenated and/or substituted by one to three radicals from the group consisting of C1-C6 alkyl and C1-C6 alkoxy; - R25 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; - R26 and R27 are hydrogen, halogen or C1-C6 alkyl; - R28, R29 and R30 are 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- haloalkylthio C6, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkenyloxy, C3-C6 alkynyl or C3-C6 alkynyloxy; - R31 is hydrogen, NH2, C1-C6 alkyl or C3-C6 alkynyl; - R32, R33 and R34 are hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy, C1-C6 alkoxy, C1 haloalkoxy -C6, C1C6 alkylthio, C1-C6 haloalkylthio, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkenyloxy, 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; - R35 and R36 are hydrogen, cyano, hydroxyl, 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 C1-C6 phenylalkyl; - Z is phenyl, pyridyl, pyridazinyl, pyrimidinyl or pyrazinyl; each optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; including its agriculturally acceptable salts or derivatives, provided that the compounds of formula (I) contain a carboxyl group.

[007] The present invention also provides agrochemical compositions comprising at least one pyridyl ether of formula (I) and customary auxiliaries for the formulation of plant protection agents.

[008] The present invention also provides herbicidal compositions comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from herbicidal compounds B (component B) and safety agents C (component W).

[009] The present invention also provides for the use of pyridyl ethers of formula (I) as herbicides, that is, for the control of weeds.

[010] The present invention further provides a method of controlling unwanted vegetation, in which a herbicide-effective amount of at least one pyridyl ether of formula (I) is allowed to act on 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 undesirable plants.

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

[012] Additional embodiments of the present invention are evident from the claims, the specification and the examples. It should be understood that the characteristics mentioned above and those yet to be illustrated below the object of the present invention can be applied not only to the combination provided in each specific case, but also to other combinations, without abandoning the scope of the present invention.

[013] As used herein, the terms “control” and “combat” are synonymous.

[014] As used herein, the expressions “undesirable vegetation” and “weed plants” are synonymous.

[015] If the pyridyl ethers of formula (I), the herbicidal compounds B and/or the safety agents C described herein are capable of forming geometric isomers, such as E/Z isomers, it is possible to use both pure isomers and mixtures thereof, in the compositions according to the present invention.

[016] If the pyridyl ethers of formula (I), the herbicidal compounds B and/or the safety agents C described herein contain one or more chirality centers and, consequently, are present as enantiomers or diastereomers, it is possible to use both , the pure enantiomers and diastereomers and mixtures thereof, in the compositions according to the present invention.

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

[018] Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium, alkaline earth metals, preferably calcium and magnesium, and transition metals, preferably manganese, copper, zinc and iron, additional ammonium and substituted ammonium, in which one to four hydrogen atoms are replaced by C1-C4 alkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy C1-C4 alkyl, C1-C4 hydroxyalkoxy C1-C4 alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyethyl- 1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl )ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), additionally phosphonium ions, sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium, such as trimethylsulfonium and sulfoxonium ions, preferably tri( C1-C4 alkyl)sulfoxonium and, finally, salts of polybasic amines, such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[019] Anions of useful acid addition salts are mainly chloride, bromide, fluoride, iodide, hydrogen sulfate, methylsulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C1-C4 alkanoic acids, preferably formate, acetate, propionate and butyrate.

[020] Pyridyl ethers of formula (I), herbicidal compounds B and/or safety agents C described herein that contain a carboxyl group can be employed in the form of an acid, in the form of an agriculturally appropriate salt as mentioned above or in the form of agriculturally acceptable derivative, such as in the form of amides, such as mono- and C1-C6 dialkylamides or arylamides, in the form of esters, such as allyl esters, propargyl esters, C1-C10 alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran -2-yl)methyl) ethers and also as thioesters, such as C1-C10 alkylthio esters. Preferred C1-C6 mono- and dialkyl amides are methyl and dimethyl amides. Preferred arylamides are, for example, anilides and 2-chloroanilides. Preferred alkyl esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or iso-octyl (2- ethylhexyl) esters. Preferred C1-C4 alkoxy C1-C4 alkyl esters are straight-chain or branched C1-C4 alkoxy ethyl esters, such as 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester. An example of a straight-chain or branched C1-C10 alkylthio ester is ethylthio ester.

[021] The organic portions mentioned in the definitions of variables R3 to R36 and Ra to Re are - like the term halogen - collective terms for individual indications of members of individual groups. The term halogen indicates, in each case, fluorine, chlorine, bromine or iodine. All hydrocarbon chains, such as all alkyl, alkenyl, alkynyl and alkoxy chains, can be straight-chain or branched, where the prefix Cn-Cm indicates, in each case, the possible number of carbon atoms in the group.

[022] Examples of these meanings are: - C1-C3 alkyl and also the C1-C3 alkyl portions of di(C1-C3 alkyl)amino and C1-C3 alkoxy C1-C3 alkyl: for example, CH3, C2H5, n-propyl and CH(CH3)2; - C1-C4 alkyl and also the C1-C4 alkyl moieties of C1-C4 phenylalkyl: e.g. CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, CH(CH3)-C2H5, CH2-CH (CH3)2 and C(CH3)3; - C1-C6 alkyl and also the C1-C6 alkyl moieties of C1-C6 cyanoalkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl, di(C1-C6 alkoxy) C1 alkyl -C6, 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, C1-C6 alkylsulfinyl C1C6 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, C3-C6 alkynyloxycarbonyl, C1-C6 alkyl, (C1-C6 alkylcarbonyl)amino, C1-C6 aminoalkyl, (C1-C6 alkyl)C1C6 aminoalkyl, di(C1-C6 alkyl)C1-C6 aminoalkyl, C1- aminocarbonylalkyl C6, (C1-C6 alkyl)aminocarbonylC1-C6 alkyl, di(C1-C6 alkyl)aminocarbonylC1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkyl, heterocyclyl C3-C6 alkyl: C1-C4 alkyl as mentioned above and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl, 1 -methylethyl, n-butyl, 1,1-dimethylethyl, n-pentyl or n-hexyl; - C1-C3 haloalkyl; C1-C3 alkyl, as mentioned above, which is fully or partially substituted by fluorine, chlorine, bromine and/or iodine, such as 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 or 1-(bromomethyl)-2-bromoethyl; - C1-C4 haloalkyl: C1-C4 alkyl, as mentioned above, which is fully or partially substituted by fluorine, chlorine, bromine and/or iodine, such as 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; - C1-C6 haloalkyl; C1-C4 haloalkyl as mentioned above and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6 -iodohexyl and dodecafluorohexyl; - C3-C6 alkenyl and also the C3-C6 alkenyl moieties of C3-C6 alkenyloxy C1-C6 alkyl, C3-C6 alkenyloxy C1-C6 alkoxy C1-C6 alkyl, C3-C6 alkenyloxycarbonyl C1-C6 alkyl: e.g. propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl- 1-propenyl, 1-methyl-2-propenyl, 2-methyl- 2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2- butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2- propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2- methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl- 3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1- dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3- dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3- dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1- ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl; - C3-C6 haloalkenyl, as well as the C3-C6 haloalkenyl moieties of C3-C6 haloalkenyloxy C1-C6 alkyl: C3-C6 alkenyl radical as mentioned above, which is fully or partially substituted by fluorine, chlorine, bromine and/or iodine, such as 2-chloroprop-2-en-1-yl, 3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-en- 1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop- 2-en-1-yl, 2,3-dibromoprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1- yl or 2,3-dibromobut-2-en-1-yl; - C3-C6 alkynyl, as well as the C3-C6 alkynyl moieties of C3-C6 alkynyloxycarbonyl C1-C6 alkyl: e.g. 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-hexinyl, 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; - C3-C6 haloalkynyl: C3-C6 alkynyl radical, as mentioned above, which is fully or partially substituted by fluorine, chlorine, bromine and/or iodine, such as 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-fluoro-hex-4-yn-1-yl or 6-iodo-hex-5-yn-1-yl; - C1-C3 alkoxy, as well as the C1-C3 alkoxy moieties of C1-C3 alkoxy C1-C3 alkyl and C1-C3 alkoxycarbonyl: for example, methoxy, ethoxy and propoxy; - C1-C4 alkoxy, as well as the C1-C4 alkoxy moieties of C1-C4 alkoxycarbonyl: for example, methoxy, ethoxy, propoxy, 1-methylethoxy butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy; - C1-C6 alkoxy, as well as the C1-C6 alkoxy moieties of C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl, di(C1-C6 alkoxy) C1-C6 alkyl, alkenyloxy C3-C6 alkoxy C1-C6 alkyl C1-C6 alkoxy and C1-C6 alkoxycarbonyl C1-C6 alkyl: C1-C4 alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2- dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy; - C1-C3 haloalkoxy: C1-C3 alkoxy radical as mentioned above, which is fully or partially substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 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, 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 and 1-(bromomethyl)-2-bromoethoxy; - C1-C4 haloalkoxy: C1-C4 alkoxy radical as mentioned above, which is fully or partially replaced by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 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, 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, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy; - 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 mentioned above, as well as, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy; - C1-C3 alkylthio: for example, methylthio, ethylthio, propylthio and 1-methylethylthio; - C1-C4 alkylthio: for example, methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio; - C1-C6 alkylthio, as well as the C1-C6 alkylthio moieties of C1-C6 alkylthio C1-C6 alkyl: C1-C4 alkylthio, as mentioned 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; - C1-C6 alkylsulfinyl (C1-C6 alkyl-S(=O)-), as well as 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- dimethylpropylsulfinyl, 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; - C1-C6 alkylsulfonyl (C1-C6 alkyl S(O)2-), as well as the 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; - (C1-C3 alkyl)amino: for example, methylamino, ethylamino, propylamino and 1-methylethylamino; - (C1-C4 alkyl)amino: for example, methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino or 1,1-dimethylethylamino; - (C1-C6 alkyl)amino: (C1-C4 alkylamino) as mentioned 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-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl- 2-methylpropylamino; di(C1-C6 alkyl)amino: di(C1-C4 alkyl)amino as mentioned above, as well as, 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-dimethyl- butyl)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, 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; - C3-C6 cycloalkyl and also the cycloalkyl moieties of C3-C6 cycloalkyl C1-C6 alkyl: monocyclic saturated hydrocarbons containing three to six ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; - C3-C6 heterocyclyl, as well as the heterocyclyl moieties of C3-C6 heterocyclyl C1-C6 alkyl: aliphatic heterocycle containing 3 to 6 ring members that, in addition to carbon atoms, contains 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and an oxygen or sulfur atom, or an oxygen or a sulfur atom, such as three- or four-membered heterocycles, such as 2-oxetanyl, 3-oxetanyl, 2-thietanyl, 3-thietanyl, 1- azetidinyl, 2-azetidinyl, 1-azetinyl and 2-azetinyl; saturated five-membered heterocycles such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4- isoxazolidinyl, 5-isoxazolidinyl, 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-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5- yl, 3-thiazolidinyl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,2,4-oxadiazolidin- 2-yl, 1,2,4-oxadiazolidin-4-yl, 1,3,4-oxadiazolidin-2-yl, 1,2,4-thiadiazolidin-2-yl, 1,2,4-thiadiazolidin-4- yl, 1,3,4-thiadiazolidin-2-yl, 1,2,4-triazolidin-1-yl and 1,3,4-triazolidin-2-yl; saturated six-membered heterocycles such as 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 1,4-dioxanyl, 1,3-dithian-5-yl, 1,3-dithianyl, 1,3-oxathian-5-yl, 1,4- oxathianyl, 2-tetrahydropyranyl, 3-tetrahydopyranyl, 4-tetrahydropyranyl, 2-tetrahydropyrimidinyl, 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-oxazin-1-yl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-6- yl, 1-morpholinyl, 2-morpholinyl and 3-morpholinyl; - heteroaryl with 5 or 6 members: aromatic heteroaryl that contains 5 or 6 ring members that, in addition to carbon atoms, contains 1 to 4 nitrogen atoms, 1 to 3 nitrogen atoms and an oxygen or sulfur atom or an atom of oxygen or sulfur, such as five-membered aromatic rings such as furyl (e.g., 2-furyl and 3-furyl), thienyl (e.g., 2-thienyl and 3-thienyl), pyrrolyl (e.g., pyrrole-2 -yl and pyrrole-3-yl), pyrazolyl (e.g. pyrazol-3-yl and pyrazol-4-yl), isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl and isoxazol-5-yl ), isothiazolyl (e.g. isothiazol-3-yl, isothiazol-4-yl and isothiazol-5-yl), imidazolyl (e.g. imidazol-2-yl and imidazol-4-yl), oxazolyl (e.g. oxazol -2-yl, oxazol-4-yl and oxazol-5-yl), thiazolyl (e.g. thiazol-2-yl, thiazol-4-yl and thiazol-5-yl), oxadiazolyl (e.g. 1,2 ,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,3,4 -oxadiazol-2-yl), thiadiazolyl (e.g., 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl and 1,3,4-thiadiazolyl-2-yl), triazolyl (e.g. 1,2,3-triazol-4-yl and 1,2,4-triazol-3 -ila); 1-tetrazolyl; six-membered aromatic rings such as pyridyl (e.g. pyridin-2-yl, pyridin-3-yl and pyridin-4-yl), pyrazinyl (e.g. pyridazin-3-yl and pyridazin-4-yl), pyrimidinyl (e.g., pyrimidin-2-yl, pyrimidin-4-yl, and pyrimidin-5-yl), pyrazin-2-yl, and triazinyl (e.g., 1,3,5-triazin-2-yl, 1,2 ,4-triazin-3-yl, 1,2,4-triazin-5-yl and 1,2,4-triazin-6-yl); - carbocycle with 3 to 7 members: monocyclic aromatic cycle with three to seven members, saturated, partially unsaturated or aromatic, which contains from three to seven ring members and comprises, in addition to carbon atoms, optionally one or two selected ring members from the group consisting of -N(R12)-, -N=N-, -C(=O)-, -O- and -S-.

[023] The preferred embodiments of the present invention mentioned here below need to be understood as being preferred, independently or in combination with each other.

[024] According to the preferred embodiment of the present invention, preference is also given to the pyridyl ethers of formula (I), in which the variables, independently or in combination with each other, have the following meanings.

[025] Pyridyl ethers of formula (I) are preferred, where: - R1 is H, F or Cl; with specific preference, H or F; of special preference, H; also preferably specifically, H or Cl; preferably special, Cl; also of specific preference, F or Cl; and with special preference, F.

[026] Pyridyl ethers of formula (I) are preferred, where: - R2 is halogen or CN; preferably, F, Cl, Br or CN; preferably specifically, F, Cl or CN; preferably special, Cl or CN; more preferably, Cl; also more preferably, CN; also with special preference, F or Cl; and most preferably, F.

[027] Pyridyl ethers of formula (I) are preferred, wherein: - R3 is H, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio; specifically preferably, H, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 alkoxy; especially preferably, it is H, C1-C3 alkyl or C1-C3 alkoxy; and more preferably, it is H, CH3 or OCH3.

[028] Pyridyl ethers of formula (I) are preferred, where: - R4 is H, halogen or C1-C3 alkyl; preferably specifically, H, F or CH3; and with special preference, H.

[029] Pyridyl ethers of formula (I) are also preferred, wherein: - R5 is OR6, SR6, NR7R8, NR6S(O)2R7 or NR6S(O)2NR7R8; preferably specifically, OR6, NR7R8, NR6S(O)2R7 or NR6S(O)2NR7R8; especially preferably, OR6, NR6S(O)2R7 or NR6S(O)2NR7R8; and especially preferably, OR6 or NR6S(O)2R7.

[030] Pyridyl ethers of formula (I) are preferred, in which: - R6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3 C6 alkynyl, C1-C6 haloalkyl, C3-C6 haloalkenyl, C3-C6 haloalkynyl , C1C6 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- alkenyloxy C6 alkyl C1C6, haloalkenyloxy C3-C6 alkyl C1-C6, alkenyloxy C3-C6 alkoxy C1-C6 alkyl C1C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, alkylsulfinyl C1-C6 alkyl, alkylsulfonyl C1C6 alkyl C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkyl, haloalkoxycarbonyl, C1-C6 alkyl, C3-C6 alkenyloxycarbonyl, C1-C6 alkyl, C3-C6 alkynyloxycarbonyl, C1-C6 alkyl, amino, (C1-alkyl) C6)amino, di(C1-C6 alkyl)amino, (C1-C6 alkylcarbonyl)amino, C1-C6 aminoalkyl, (C1-C6 alkyl)C1-C6 aminoalkyl, di(C1-C6 alkyl)C1-C6 aminoalkyl, aminocarbonylalkyl C1-C6, (C1-C6 alkyl)aminocarbonylC1-C6alkyl or di(C1-C6 alkyl)aminocarbonylC1-C6alkyl; -N=CR9R10; wherein R9 and R10, independently of each other, are H, C1-C4 alkyl or phenyl; C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3C6 heterocyclyl, phenyl, C1-C4 phenylalkyl or 5- or 6-membered heteroaryl; wherein each cycloalkyl, heterocyclyl, phenyl or heteroaryl ring can be replaced by one to four substituents selected from R11 or 3 to 7 membered carbocycle; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of -N(R9)-, -N=N-, -C(=O)-, -O - and -S-; and wherein the carbocycle is optionally substituted by one to four substituents selected from R11; wherein R11 is halogen, NO2, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 alkoxycarbonyl; 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; specifically preferably, it is hydrogen, C1-C6 alkyl, C3C6 alkenyl, C3-C6 alkynyl or C1-C6 haloalkyl; especially preferably, it is hydrogen, C1-C6 alkyl or C3C6 alkynyl; and more preferably, it is hydrogen, CH3, C2H5 or CH2C=CH.

[031] Pyridyl ethers of formula (I) are also preferred, where: - R7 is H or C1-C6 alkyl; that: that: that: that: of greater preference, H; and also more preferably, C1-C6 alkyl.

[032] Pyridyl ethers of formula (I) are also preferred, in which - R8 is H or C1-C6 alkyl; most preferably, H; and also more preferably, C1-C6 alkyl.

[033] Pyridyl ethers of formula (I) are also preferred, in which - R9 is phenyl or C1-C4 alkyl; preferably specifically, phenyl or CH3; also specifically preferably, phenyl; and also specifically preferably, C1-C4 alkyl.

[034] Pyridyl ethers of formula (I) are also preferred, in which - R10 is phenyl or C1-C4 alkyl; preferably specifically, phenyl or CH3; also specifically preferably, phenyl; and also specifically preferably, C1-C4 alkyl.

[035] Pyridyl ethers of formula (I) are also preferred, in which - R11 is halogen or C1-C6 alkyl; preferably specifically, F, Cl or CH3; also of specific preference, halogen; preferably special, F or Cl; also specifically preferably, C1-C6 alkyl; and especially preferably, CH3.

[036] Pyridyl ethers of formula (I) are also preferred, where: - n is 1 or 2; of specific preference, 2; and also of specific preference, 1.

[037] Pyridyl ethers of formula (I) are also preferred, wherein: - Q is O or S; of specific preference, O.

[038] Pyridyl ethers of formula (I) are also preferred, where: - W is O; and also preferably, S.

[039] Pyridyl ethers of formula (I) are also preferred, where: - X is O; and also preferably, S.

[040] According to the preferred embodiment of the present invention, preference is also given to the pyridyl ethers of formula (I), in which the variables, independently or in combination with each other, have the following meanings: - Y is preferably Y2, Y13, Y20, Y31, Y37, Y38, Y39, Y42, Y48, Y55, Y65, Y66, Y67, Y68 or Y76; preferably specifically, Y2, Y20, Y31, Y38, Y48, Y55, Y65, Y67, Y68 or Y76; especially preferably Y2, Y20, Y38, Y55, Y65, Y66, Y67 or Y76; more preferably, Y2, Y20, Y55, Y65, Y67 or Y76; also preferably, Y is preferably Y2, Y13, Y20, Y31, Y37, Y38, Y39, Y42, Y48, Y55, Y65, Y66, Y67 or Y68; preferably specifically, Y2, Y20, Y31, Y38, Y48, Y55, Y65, Y67 or Y68; especially preferably Y2, Y20, Y38, Y55, Y65, Y66 or Y67; and more preferably, Y2, Y20, Y55, Y65 or Y67; - A1 and A2 are preferably oxygen; and also preferably, they are sulfur; - A3 is preferably oxygen; and also most preferably, it is sulfur; - A4 is preferably oxygen; and also preferably, it is sulfur; - R12, R13, R14, R15, R16, R17 and R18 are preferably H, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylthio or C1-C6 alkylsulfonyl; or - R12 and R13, together with the atoms to which they are bonded, form a cycle with five or six members; - which is saturated, partially unsaturated or aromatic; which may comprise, in addition to carbon atoms, one to four nitrogen atoms, one oxygen atom or one sulfur atom; and - which, for its part, can be totally or partially halogenated and/or substituted by one to three C1-C6 alkyl groups; specifically preferably, they are H, C1-C6 alkyl or C1-C6 haloalkyl; or - R12 and R13, together with the atoms to which they are bonded, form a six-membered cycle, which is saturated; - and specific preference, are H, C1-C6 alkyl or C1-C6 haloalkyl; - and most preferably, it is H, CH3 or CF3; - also preferably, R12, R13 and R14 are preferably H, hydroxy, C1-C6 alkyl or C1-C6 haloalkyl; specifically preferably, they are H, hydroxy or C1-C6 haloalkyl; and especially preferably, they are H, hydroxy or CF3; - also preferably, R12 is preferably C1-C6 alkyl or C1-C6 haloalkyl; preferably specifically, CH3 or CF3; and especially preferably, CF3; - also preferably, R13 is H; - also preferably, R14 is preferably H, hydroxy, CH3 or CF3; preferably specifically, H or hydroxy; and especially preferably, hydroxy; - R16 and R17 are, more preferably, C1-C6 haloalkyl; - R18 is preferably higher than CH3; - R19, R20, R21, R22, R23 and R24 are preferably hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfinyl or C1-C6 alkylsulfonyl; or - R21 and R22, together with the atoms to which they are bonded, form a five- or six-membered cycle; which is saturated, partially unsaturated or aromatic; which may comprise, in addition to carbon atoms, one to four nitrogen atoms, one or two oxygen atoms or one or two sulfur atoms; and which, for its part, may be totally or partially halogenated and/or substituted by one or more C1-C6 alkyl groups; specifically preferably, they are hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 haloalkoxy; or - R21 and R22, together with the atoms to which they are bonded, form a five- or six-membered cycle; which is saturated; and which, for its part, may be totally or partially halogenated and/or substituted by one or more C1-C6 alkyl groups; especially preferably, they are C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 haloalkoxy; or - R21 and R22, together with the atoms to which they are bonded, form a six-membered cycle, which is saturated; and more preferably, they are CH3, CF3, CF2H or OCF2H; - R25 is preferably C1-C6 alkyl or C1-C6 haloalkyl; - R26 and R27 are preferably hydrogen, halogen or C1-C6 alkyl; and specifically preferably, C1-C6 alkyl; - R28, R29 and R30 are preferably hydrogen, halogen or C1-C6 alkyl; more preferably, halogen or C1-C6 alkyl; preferably superior, halogen; also preferably higher, C1-C6 alkyl; and also preferably higher, hydrogen; - R31 is preferably C1-C6 alkyl; - R32, R33 and R34 are preferably hydrogen, halogen, C1-C6 alkyl or C1-C6 haloalkyl; and specifically preferably, C1-C6 haloalkyl; - R35 and R36 are preferably hydrogen, amino, C1-C6 alkyl or C1-C6 haloalkyl; and specifically preferably, C1-C6 alkyl.

[041] Pyridyl ethers of formula (I) are also preferred, wherein: - Z is phenyl or pyridyl; each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; preferably, phenyl; which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; also preferably, pyridyl; which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy.

[042] Pyridyl ethers of formula (I) are also preferred, wherein: - Z is phenyl or pyridyl; each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; preferably, it is phenyl or pyridyl; each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; preferably specifically, phenyl or pyridyl; each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen or C1-C6 alkyl; especially preferably, phenyl or pyridyl; each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of F, Cl or CH3; and more preferably, phenyl or pyridyl; each of which is unreplaced.

[043] Pyridyl ethers of formula (I) are also preferred, wherein: - Z is phenyl; which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; preferably, phenyl; which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; also specifically preferably, phenyl; which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen or C1-C6 alkyl; especially preferably, phenyl; which is optionally substituted by 1 to 4 substituents selected from the group consisting of F, Cl or CH3; and most preferably, it is unsubstituted phenyl.

[044] Pyridyl ethers of formula (I) are also preferred, wherein: - Z is pyridyl; which is optionally substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; preferably, pyridyl; which is optionally substituted by 1 to 3 substituents selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; specifically preferably, pyridyl; which is optionally substituted by 1 to 3 substituents selected from the group consisting of halogen or C1-C6 alkyl; especially preferably, pyridyl; which is optionally substituted by 1 to 3 substituents selected from the group consisting of F, Cl or CH3; and most preferably, it is unsubstituted.

[045] Pyridyl ethers of formula (I) are also preferred, in which: Z is selected from the group consisting of Z1 to Z29: where: 1 indicates the connection point from Z to X; 2 * indicates the connection point from Z to Q; and - Ra, Rb, Rc, Rd and Re, independently of each other, are: H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; preferably, H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; specifically preferably, H, halogen or C1-C6 alkyl; especially preferably H, F, Cl or CH3; and most preferably, H.

[046] Pyridyl ethers of formula (I) are also preferred, in which: - Z is selected from the group consisting of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11 , Z12, Z13 and Z21 as defined above; preferably specifically, selected from the group consisting of Z1, Z2, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11 and Z21, as defined above; preferably special, selected from the group consisting of Z1, Z4, Z5, Z6 and Z7, as defined above; and especially preferably, selected from the group consisting of Z1, and Z7, as defined above.

[047] Pyridyl ethers of formula (I) are also preferred, in which: - Z is selected from the group consisting of Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11 , Z12, Z13 and Z21 as defined above; where - Ra, Rb, Rc, Rd and Re, independently of each other, are: H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; preferably, H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; specifically preferably, H, halogen or C1-C6 alkyl; especially preferably H, F, Cl or CH3; and more preferably, H; preferably specifically, selected from the group consisting of Z1, Z2, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11 and Z21, as defined above; where - Ra, Rb, Rc, Rd and Re, independently of each other, are: H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; preferably, H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; specifically preferably, H, halogen or C1-C6 alkyl; especially preferably H, F, Cl or CH3; and more preferably, H; preferably special, selected from the group consisting of Z1, Z4, Z5, Z6 and Z7, as defined above; where - Ra, Rb, Rc, Rd and Re, independently of each other, are: H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; preferably, H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; specifically preferably, H, halogen or C1-C6 alkyl; especially preferably, H, F, Cl or CH3; and more preferably, H; most preferably selected from the group consisting of Z1 and Z7 as defined above, wherein - Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-C6 alkyl, haloalkyl C1-C6, C1-C6 alkoxy or C1-C6 haloalkoxy; preferably, H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; specifically preferably, H, halogen or C1-C6 alkyl; especially preferably H, F, Cl or CH3; and most preferably, H.

[048] Pyridyl ethers of formula (I) are also preferred, wherein: - R1 is H or F; and - R2 is F, Cl or CN.

[049] Pyridyl ethers of formula (I) are also preferred, where: - R3 is H, C1-C3 alkyl or C1-C3 alkoxy; and - R4 is H.

[050] Pyridyl ethers of formula (I) are also preferred, in which: - R5 is OR6, NR6S(O)2R7 or NR6S(O)2NR7R8, in which - R6 is hydrogen, C1-C6 alkyl, C3-alkenyl or C3-C6 cycloalkyl C1-C6 alkyl; and - R7 and R8 are C1-C6 alkyl.

[051] Pyridyl ethers of formula (I), where n is 1, are also preferred.

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

[053] Pyridyl ethers of formula (I) are also preferred, in which: - R1 is H or halogen; - R2 is halogen or CN; - R3 is H, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio; - R4 is H; - R5 is OR6, SR6, NR7R8, NR6S(O)2R7 or NR6S(O)2NR7R8; where - R6 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, haloalkoxy C1-C6 alkyl, C3-C6 alkenyloxy C1-C6 alkyl, haloalkenyloxy C3-C6 alkyl C6, C3-C6 alkenyloxy C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1C6 alkylsulfonyl C1-C6 alkyl, C1-C6 alkylcarbonyl C1-C6 alkyl, alkoxycarbonyl C1-C6 alkyl C1-C6 alkyl, C1-C6 haloalkoxycarbonyl C1-C6 alkyl, C3-C6 alkenyloxycarbonyl C1-C6 alkyl, amino, (C1-C6 alkyl)amino, di(C1-C6 alkyl)amino, (C1-C6 alkylcarbonyl )amino, C1-C6 aminoalkyl, (C1-C6 alkyl)C1-C6 aminoalkyl, di(C1-C6 alkyl)C1-C6 aminoalkyl, aminocarbonylC1-C6alkyl, (C1-C6 alkyl)aminocarbonylC1-C6alkyl or di (C1-C6 alkyl)aminocarbonylC1-C6alkyl; -N=CR9R10; wherein R9 and R10, independently of each other, are H, C1-C4 alkyl or phenyl; C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3C6 heterocyclyl, phenyl, C1-C4 phenylalkyl or 5- or 6-membered heteroaryl; wherein each cycloalkyl, heterocyclyl, phenyl or heteroaryl ring can be replaced by one to four substituents selected from R11 or 3 to 7 membered carbocycle; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of -N(R11)-, -N=N-, -C(=O)-, -O - and -S-; and wherein the carbocycle is optionally substituted by one to four substituents selected from R11; - R7 is C1-C6 alkyl; - R8 is H or C1-C6 alkyl; - R9 is phenyl or CH3; - R10 is phenyl or CH3; - R11 is halogen or C1-C6 alkyl; - n is 1 or 2; Q is O, S, SO, SO2, NH or (C1-C3 alkyl)N; W is O; X is O; and Z is Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11, Z12, Z13 and Z21, as defined above, where Ra, Rb, Rc, Rd and Re, independently of each other , are H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; Particularly preferred are the pyridyl ethers of formula (I), wherein: - R1 is H or halogen; - R2 is halogen or CN; - R3 is H, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 alkoxy; - R4 is H; - R5 is OR6, NR7R8, NR6S(O)2R7 or NR6S(O)2NR7R8; where - R6 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- alkylcarbonyl C6 C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl or C3-C6 cycloalkyl C1-C6 alkyl; - R7 is C1-C6 alkyl; - R8 is H or C1-C6 alkyl; - n is 1; - Q is O, S, SO, SO2, NH or (C1-C3 alkyl)N; - W is O; - X is O; and - Z is selected from the group consisting of Z1, Z2, Z4, Z5, Z6, Z7, Z8, Z9, Z10, Z11 and Z21 as defined above, where Ra, Rb, Rc, Rd and Re, independently among themselves, they are H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; Particular preference is given to the pyridyl ethers of formula (I), wherein: - R1 is H, F or Cl; - R2 is F, Cl or CN; - R3 is H, C1-C3 alkyl or C1-C3 alkoxy; - R4 is H; - R5 is OR6 or NR6S(O)2R7, where - R6 is hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3 C6 alkynyl or C1-C6 haloalkyl; and - R7 is C1-C6 alkyl; - n is 1; - Q is O or S; - W is O; - X is O; - Z is selected from the group consisting of Z1, Z4, Z5, Z6 and Z7 as defined above, wherein Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-alkyl C6, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; More preferred are the pyridyl ethers of formula (I), wherein: - R1 is H, F or Cl; - R2 is F, Cl or CN; - R3 is H, CH3 or OCH3; - R4 is H; - R5 is OR6 or NR6S(O)2R7; where - R6 is hydrogen, C1-C6 alkyl or C3-C6 alkynyl; and - R7 is C1-C6 alkyl; - n is 1; - Q is O; - W is O; - X is O; and - Z is selected from the group consisting of Z1 and Z7 as defined above, wherein Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-C6 alkyl, C1-haloalkyl C6, C1-C6 alkoxy or C1-C6 haloalkoxy.

[054] Pyridyl ethers of formula (I) are also preferred, where: - R1 is H, F or Cl; - R2 is F, Cl or CN; - R3 is H, CH3 or OCH3; - R4 is H; - R5 is OR6, SR6, NR7R8, NR6OR6, NR6S(O)2R7 or NR6S(O)2NR7R8, where - R6 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, haloalkoxy C1-C6 alkyl C1-C6, alkenyloxy C3-C6 alkyl C1-C6, haloalkenyloxy C3-C6 alkyl C1-C6, alkenyloxy C3-C6 alkoxy C1-C6 alkyl, alkylthio C1-C6 alkyl C1-C6, alkylsulfinyl C1 -C6 C1-C6 alkyl, C1C6 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 alkyl)amino, di(C1-C6 alkyl)amino, (C1-C6 alkylcarbonyl)amino, C1-C6 aminoalkyl, (C1-C6 alkyl)C1-aminoalkyl C6, di(C1-C6 alkyl)C1-C6 aminoalkyl, C1-C6 aminocarbonylalkyl, (C1-C6 alkyl)aminocarbonylC1-C6alkyl or di(C1-C6 alkyl)aminocarbonylC1-C6alkyl; -N=CR9R10, where R9 and R10, independently of each other, are H, C1-C4 alkyl or phenyl; C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C6 heterocyclyl, C3-C6 heterocyclyl, C1-C6 alkyl, phenyl, C1-C4 phenylalkyl or 5- or 6-membered heteroaryl; wherein each cycloalkyl, heterocyclyl, phenyl or heteroaryl ring can be replaced by one to four substituents selected from R14 or 3 to 7 membered carbocycle; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of: -N(R9)-, -N=N-, -C(=O)-, - O- and -S-; and wherein the carbocycle is optionally substituted by one to four substituents selected from R11; wherein R11 is halogen, NO2, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 alkoxycarbonyl; - R7 and R8, independently of each other, are R9 or together they form a carbocycle with 3 to 7 members; wherein the carbocycle optionally contains, in addition to carbon atoms, one or two ring members selected from the group consisting of -N(R10)-, -N=N-, -C(=O)-, -O - and -S-; and - m that the carbocycle is optionally substituted by one to four substituents selected from R11; - n is 1; - Q is O; - W is O; - X is O; and - Z is selected from the group consisting of Z1 and Z7 as defined above, wherein Ra, Rb, Rc, Rd and Re, independently of each other, are H, halogen, CN, C1-C6 alkyl, C1-haloalkyl C6, C1-C6 alkoxy or C1-C6 haloalkoxy.

[055] Specific preference is given to pyridyl ethers of formula (Ia) (corresponding to formula (I) in which Y is Y2, R19 is Br, R20 is CF3, R21 is CH3 and R4 is H, n is 1, Q , W and X are O and Z is Z-1 as defined, where Ra, Rb, Rc and Rd are H: wherein the variables R1, R2, R3 and R5 have the meanings, particularly the preferred meanings, as defined above.

[056] Special preference is given to compounds of formulas Ia1 to Ia36 of Table A, in which the definitions of the variables R1, R2, R3 and R5 are of specific importance for the compounds according to the present invention, not just in combination among themselves, but also separately in each case. TABLE A

[057] Also preferred are the pyridyl ethers of formula (Ib), particularly preferred are the pyridyl ethers of formulas (Ib1) to (Ib36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y2, where R28 is Cl, R23 is OCHF2 and R24 is CH3:

[058] Also preferred are the pyridyl ethers of formula (Ic), particularly preferred are the pyridyl ethers of formulas (Ic1) to (Ic36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y13, where A1 and A2 are O, R19 is H and R21 and R22 together form -(CH2-CHF-CH2)-:

[059] Also preferred are the pyridyl ethers of formula (Id), particularly preferred are the pyridyl ethers of formulas (Id1) to (Id36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y13, where A1 and A2 are O, R19 is H and R21 and R22 together form -(CH2-CHF-CH2)- in the form of the stereoisomer (6S, 7aR):

[060] Also preferred are the pyridyl ethers of formula (Ie), particularly preferred are the pyridyl ethers of formulas (Ie1) to (Ie36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y20, where A1 is O, R21 is CHF2 and R22 is CH3:

[061] Also preferred are the pyridyl ethers of formula (If), particularly preferred are the pyridyl ethers of formulas (If1) to (If36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y20, where A1 is O and R21 and R22 together form -(CH2)4-:

[062] Also preferred are the pyridyl ethers of formula (Ig), particularly preferred are the pyridyl ethers of formulas (Ig1) to (Ig36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y31, where A1 and A2 are O and R26 and R27 are CH3:

[063] Also preferred are the pyridyl ethers of formula (Ih), particularly preferred are the pyridyl ethers of formulas (Ih1) to (Ih36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y37, where A1 is O, A4 is S and R21 and R22 together form - (CH2)4-:

[064] Also preferred are the pyridyl ethers of formula (Ii), particularly preferred are the pyridyl ethers of formulas (Ii1) to (Ii36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y38, where A1 is O and R28 is C(CH3)3:

[065] Also preferred are the pyridyl ethers of formula (Ik), particularly preferred are the pyridyl ethers of formulas (Ik1) to (Ik36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y39, where A1 is S and R21 and R22 together form: -(CH2-C(CH3)2-CH2)-:

[066] Also preferred are the pyridyl ethers of formula (Il), particularly preferred are the pyridyl ethers of formulas (Il1) to (Il36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y42, where R30 is Cl, R14 is H, R16 is CF3 is R5 is H:

[067] Also preferred are the pyridyl ethers of formula (Im), particularly preferred are the pyridyl ethers of formulas (Im1) to (Im36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y48, where A1 is O, R32 is CF3, and R35 is CH3:

[068] Also preferred are the pyridyl ethers of formula (In), particularly preferred are the pyridyl ethers of formulas (In1) to (In36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y55, where A1 is O, R28 is H, R17 is CF3 and R18 is CH3:

[069] Also preferred are the pyridyl ethers of formula (Io), particularly preferred are the pyridyl ethers of formulas (Io1) to (Io36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y65, where A1 is O, R12 is H, R13 is CF3 and R35 is CH3:

[070] Also preferred are the pyridyl ethers of formula (Ip), particularly preferred are the pyridyl ethers of formulas (Ip1) to (Ip36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y66, where A1 is O, R12 is CF3, R13 is H and R35 is CH3:

[071] Also preferred are the pyridyl ethers of formula (Iq), particularly preferred are the pyridyl ethers of formulas (Iq1) to (Iq36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y67, where A1 and A2 are O, A3 is S and R35 and R36 are CH3:

[072] Pyridyl ethers of formula (Ir) are also preferred, particularly preferred are pyridyl ethers of formulas (Ir1) to (Ir36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y68, where A1 and A2 are O and R12 and R13 together form - (CH2)4-:

[073] The pyridyl ethers of formula (I.s) are also preferred, particularly preferred are the pyridyl ethers of formulas (I.s.1) to (I.s.36), which are different from the corresponding pyridyl ethers of formulas (I.a.1) to (I.a.36) only because Z is Z-7 as defined, where Ra, Rb and Rc are H:

[074] Pyridyl ethers of formula (It) are also preferred, particularly preferred are pyridyl ethers of formulas (It1) to (It36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y2, where R28 is Cl, R23 is OCHF2, R24 is CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[075] Also preferred are the pyridyl ethers of formula (Iu), particularly preferred are the pyridyl ethers of formulas (Iu1) to (Iu36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y13, where A1 and A2 are O, R19 is H, R21 and R22 together form -(CH2-CHF-CH2)- and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[076] Also preferred are the pyridyl ethers of formula (Iv), particularly preferred are the pyridyl ethers of formulas (Iv1) to (Iv36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y13, where A1 and A2 are O, R19 is H and R21 and R22 together form -(CH2-CHF-CH2)-, in the form of the stereoisomer (6S, 7aR) and Z is Z-7 as defined, where Ra , Rb and Rc are H:

[077] Also preferred are the pyridyl ethers of formula (Iw), particularly preferred are the pyridyl ethers of formulas (Iw1) to (Iw36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y20, where A1 is O, R21 is CHF2, R22 is CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[078] Also preferred are the pyridyl ethers of formula (Ix), particularly preferred are the pyridyl ethers of formulas (Ix1) to (Ix36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y20, where A1 is O, R21 and R22 together form -(CH2)4- and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[079] Also preferred are the pyridyl ethers of formula (Iy), particularly preferred are the pyridyl ethers of formulas (Iy1) to (Iy36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y31, where A1 and A2 are O, R26 and R27 are CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[080] Also preferred are the pyridyl ethers of formula (Iz), particularly preferred are the pyridyl ethers of formulas (Iz1) to (Iz36), which are different from the corresponding pyridyl ethers of formulas (Ia1) to (Ia36) only because Y is Y37, where A1 is O, A4 is S, R21 and R22 together form -(CH2)4- and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[081] Pyridyl ethers of formula (I.aa) are also preferred, particularly preferred are pyridyl ethers of formulas (I.aa.1) to (I.aa.36), which are different from the corresponding pyridyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y38, where A1 is O, R28 is C(CH3)3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[082] Pyridyl ethers of formula (I.ab) are also preferred, particularly preferred are pyridyl ethers of formulas (I.ab.1) to (I.ab.36), which are different from the corresponding pyridyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y39, where A1 is S, R21 and R22 together form -(CH2-C(CH3)2-CH2)- and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[083] Pyridyl ethers of formula (I.ac) are also preferred, particularly preferred are pyridyl ethers of formulas (I.ac.1) to (I.ac.36), which are different from the corresponding pyridyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y42, where R30 is Cl, R14 is H, R16 is CF3, R15 is H and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[084] Pyridyl ethers of formula (I.ad) are also preferred, particularly preferred are pyridyl ethers of formulas (I.ad.1) to (I.ad.36), which are different from the corresponding pyridyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y48, where A1 is O, R32 is CF3, R35 is CH3, and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[085] Pyridyl ethers of formula (I.ae) are also preferred, particularly preferred are pyridyl ethers of formulas (I.ae.1) to (I.ae.36), which are different from the corresponding pyridyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y55, where A1 is O, R28 is H, R17 is CF3, R18 is CH3 and Z is Z- 7 as defined, where Ra, Rb and Rc are H:

[086] Pyridyl ethers of formula (I.af) are also preferred, particularly preferred are pyridyl ethers of formulas (I.af.1) to (I.af.36), which are different from the corresponding pyridyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y65, where A1 is O, R12 is H, R13 is CF3, R35 is CH3 and Z is Z- 7 as defined, where Ra, Rb and Rc are H:

[087] Pyridyl ethers of formula (I.ag.) are also preferred, particularly preferred are pyridyl ethers of formulas (I.ag.1) to (I.ag.36), which are different from the corresponding pyridyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y66, where A1 is O, R12 is CF3, R13 is H, R35 is CH3 and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[088] The pyridyl ethers of the formula (I.ah.) are also preferred, particularly preferred are the pyridyl ethers of the formulas (I.ah.1) to (I.ah.36), which are different from the corresponding pyridyl ethers of the formulas ( Ia1) to (Ia36) only because Y is Y67, where A1 and A2 are O, A3 is S, R35 and R36 is CH3 and Z is Z- 7 as defined, where Ra, Rb and Rc are H:

[089] Pyridyl ethers of formula (I.ai) are also preferred, particularly preferred are pyridyl ethers of formulas (I.ai.1) to (I.ai.36), which are different from the corresponding pyridyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y68, where A1 and A2 are O, R12 and R13 together form -(CH2)4- and Z is Z-7 as defined, where Ra, Rb and Rc are H:

[090] Pyridyl ethers of formula (I.ak) are also preferred, particularly preferred are pyridyl ethers of formulas (I.ak.1) to (I.ak.36), which are different from the corresponding pyridyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y76, where A1 and A2 are O, R12 is CF3, R13 and R15 are H, R14 is OH and R22 is H:

[091] Pyridyl ethers of formula (I.al.) are also preferred, particularly preferred are pyridyl ethers of formulas (I.al.1) to (I.al.36), which are different from the corresponding pyridyl ethers of formulas ( Ia1) to (Ia36) only because Y is Y76, where A1 and A2 are O, R12 is CF3, R13 and R15 are H, R14 is OH and R22 is H:

[092] The pyridyl ethers of formula (I) according to the present invention can be prepared by standard organic chemistry processes, for example, by processes A and E below.

PROCESS A

[093] Pyridyl ethers of formula (I) can be prepared by reacting pyridines of formula (II) with compounds of formula (III) in the presence of base:

[094] Among the pyridines of formula (ll): L1 is a residual group such as halogen, C1-C6 alkyl sulfonate or aryl sulfonate; preferably, F, Cl, C1-C6 alkyl sulfonate or aryl sulfonate; especially preferably, F, Cl, OSO2CH3 (mesylate) or OSO2C6H4CH3 (tosylate); more preferably, F or Cl.

[095] The compounds of formula (lll) can also be used in the form of their salts, particularly sodium and potassium salts, and, in this case, the presence of base is not necessary.

[096] The reaction of pyridines (II) with compounds (III) in the presence of base is normally carried out from 0 °C to the boiling point of the reaction mixture, preferably from 40 °C to 100 °C.

[097] The reaction can, in principle, be conducted in substance. Preference is given, however, to the reaction of pyridines of formula (II) with compounds of formula (III) in organic solvent.

[098] In principle, all solvents are suitable that are capable of dissolving the pyridines of formula (II) and the compounds of formula (III), at least partially and, preferably, completely under the reaction conditions.

[099] Examples of suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8 alkanes; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- 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), dioxane, 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 and cyclohexanone; as well as bipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, 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-pyrrolidinone (NMP).

[100] Preferred solvents are ethers, nitriles, ketones and bipolar aprotic solvents, as defined above.

[101] Most preferred solvents are ethers and bipolar aprotic solvents, as defined above.

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

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

[104] Examples of suitable metal-containing bases are inorganic compounds, such as alkali metal oxides, alkaline earth metal oxides, and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium 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, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; metallic organic compounds, preferably alkali metal alkyls, such as methyl lithium, butyl lithium and phenyl lithium, alkyl magnesium halides such as methyl magnesium chloride, as well as alkali metal alkoxides and alkaline earth metals, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium; carbonates of alkali metals and alkaline earth metals, such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, cesium carbonate and calcium carbonate, as well as hydrogen carbonates (bicarbonates) of alkali metals, such as hydrogen lithium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates, such as potassium phosphate and calcium phosphate; and, additionally, organic bases such as tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine, 4-dimethylaminopyridine and also bicyclic amines.

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

[106] Preferred bases are hydrides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, as well as hydrogen carbonates (bicarbonates) of alkali metals; alkali metal and alkaline earth metal phosphates; metallic organic compounds, alkyl magnesium halides and alkali metal and alkaline earth metal alkoxides; and, additionally, organic bases, such as tertiary amines, pyridine, substituted pyridines and also bicyclic amines.

[107] Especially preferred bases are carbonates of alkali metals and alkaline earth metals, organic metal compounds, alkyl magnesium halides and also alkoxides of alkali metals and alkaline earth metals; and, additionally, organic bases, such as tertiary amines, pyridine, substituted pyridines and also bicyclic amines.

[108] The term base, as used herein, also includes mixtures of two or more, preferably two of the above compounds. Specific preference is given to using a foundation.

[109] Bases are generally used in excess, more preferably 1 to 3 equivalents based on the pyridines of formula (II) and can also be used as a solvent.

[110] For the reaction, the pyridines of formula (II), the compound of formula (III) and the base can be intrinsically brought into contact in any way.

[111] Consequently, the reaction partners and the base can be introduced into the reaction vessel and react separately, simultaneously or successively.

[112] Reagents 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.

[113] The reaction can be carried out under atmospheric pressure, under reduced pressure or under elevated pressure, if appropriate, under inert gas, continuously or in batches.

[114] The end of the reaction can be easily determined by those skilled in the art using routine methods.

[115] Reaction mixtures are worked up in a customary manner, for example, by means of filtration, mixing with water, phase separation and, if appropriate, chromatographic purification of the crude product. 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 moderately elevated temperature.

[116] If the intermediates and final products are obtained in the form of solids, purification can also be conducted through recrystallization or digestion.

PROCESS B

[117] Alternatively, pyridyl ethers of formula (I) can also be prepared by reacting compounds of formula (IV) with alkylating agents of formula (V) in the presence of base in a manner analogous to known processes (e.g. WO 11/137088):

[118] Among the alkylating agents of formula (V): - L2 is a residual group such as halogen, C1-C6 alkyl sulfonate or aryl sulfonate; preferably, Cl, Br, I, C1-C6 alkyl sulfonate or aryl sulfonate; especially preferably, Cl, Br or I; and more preferably, Cl or Br.

[119] The reaction of compounds of formula (IV) with alkylating agents of formula (V) in the presence of base is normally conducted from 0 °C to the boiling point of the reaction mixture, preferably from 20 °C to 100 ° W.

[120] The reaction can, in principle, be conducted in substance. Preference is given, however, to the reaction of the compounds of formula (IV) with the alkylating agents of formula (V) in organic solvent.

[121] In principle, all solvents are suitable that are capable of dissolving the compounds of formula (IV) and the alkylating agents of formula (V), at least partially and, preferably, completely under the reaction conditions.

[122] Examples of suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8 alkanes; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- 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), dioxane, 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 and cyclohexanone; as well as bipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, 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-pyrrolidinone (NMP).

[123] Preferred solvents are ethers, nitriles, ketones and bipolar aprotic solvents, as mentioned above. Most preferred solvents are ethers and bipolar aprotic solvents, as mentioned above. It is also possible to use mixtures of the mentioned solvents.

[124] Examples of suitable bases include metal-containing bases and nitrogen-containing bases. Examples of suitable metal-containing bases are inorganic compounds such as alkali metal hydroxides, 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 oxides, 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; carbonates of alkali metals and alkaline earth metals, such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, cesium carbonate and calcium carbonate, as well as hydrogen carbonates (bicarbonates) of alkali metals, such as hydrogen lithium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates, such as potassium phosphate and calcium phosphate; metallic organic compounds, preferably alkali metal alkyls, such as methyl lithium, butyl lithium and phenyl lithium; alkyl magnesium halides, such as methyl magnesium chloride, as well as alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium; and, additionally, organic bases such as tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine, 4-dimethylaminopyridine and also bicyclic amines.

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

[126] Preferred bases are hydrides of alkali metals and alkaline earth metals, carbonates of alkali metals and alkaline earth metals, as well as hydrogen carbonates (bicarbonates) of alkali metals; alkali metal and alkaline earth metal phosphates; metallic organic compounds, alkyl magnesium halides and alkali metal and alkaline earth metal alkoxides; and, additionally, organic bases, such as tertiary amines, pyridine, substituted pyridines and also bicyclic amines.

[127] Especially preferred bases are carbonates of alkali metals and alkaline earth metals, organic metal compounds, alkyl magnesium halides and also alkoxides of alkali metals and alkaline earth metals; and, additionally, organic bases, such as tertiary amines, pyridine, substituted pyridines and also bicyclic amines.

[128] The term base, as used herein, also includes mixtures of two or more, preferably two of the above compounds. Specific preference is given to using a foundation.

[129] Bases are generally used in equimolar or excess amounts, more preferably with 1 to 20 molar equivalents based on the compounds of formula (IV), and can also be used as solvents.

[130] The bases are preferably used in 1 to 5 molar equivalents, most preferably 1 to 3 molar equivalents, more preferably 1 to 2 molar equivalents, based on the compounds of formula (IV).

[131] It may be advantageous to add the compensation base over a period of time.

[132] Reagents 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.

[133] For the reaction, the compound (IV), the alkylating agent (V) and the base can be intrinsically brought into contact in any way.

[134] The reaction can be carried out under atmospheric pressure, under reduced pressure or under elevated pressure, if appropriate, under inert gas, continuously or in batches.

[135] The end of the reaction can be easily determined by those skilled in the art using routine methods.

[136] Reaction mixtures are worked up in a customary manner, for example, by means of filtration, mixing with water, phase separation and, if appropriate, chromatographic purification of the crude product. 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 moderately elevated temperature. If the intermediates and final products are obtained in solid form, purification can also be conducted through recrystallization or digestion.

[137] Alternatively, pyridyl ethers of formula (I), where Y is a heterocycle, which is linked through an N atom to the pyridine ring, can also be prepared from amino compounds of formula (VI) of analogous to known processes:

[138] The methods used to convert compounds (VI) into pyridyl ethers of formula (I) depend on the nature of the Y group.

[139] These methods are described, among others, in Chemical Biology & Drug Design 2014, 84 (4), 431-442 (Y8, Y9), Bioorganic & Medicinal Chemistry 2010, 18 (22), 7948-7956 (Y10) , JP 01139580 (Y11), EP 1,157,991 (Y12), EP 311,135 (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 75,267 (Y18), EP 863,142 (Y19), EP 334,055 (Y17, Y20, Y38), WO 96/18618 (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), US 5,726,126 (Y36), WO 96/02523 (Y37), WO 92/21684 (Y37 ), EP 334,055 (Y17, Y20, Y38), WO 93/03043 (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 Chemie 1986, 26 (4), 134-136 (Y61), EP 371,240 (Y63, Y64), WO 98/41093 (Y66) , WO 10/145992 (Y67), WO 04/087694 (Y68), WO 2000/013508 (Y69) and CN 1355164 (Y70).

PROCESS D

[140] Alternatively, pyridyl ethers of formula (I), where Y is a heterocycle, which is linked through a C atom to the pyridine ring, can also be prepared by means of a cross-coupling reaction of compounds of formula (VII) with compounds of formula (VIII) in the presence of a transition metal catalyst in a manner analogous to known processes (e.g. WO 95/22547 (Y2), WO 98/07720 (Y42), WO 02/042275 (Y42 ), JP 2009137851 (Y45) and WO 17/036266 (Y65):

[141] Among the compounds of formula (VII): - L3 is a residual group such as halogen or OSO2CF3 (triflate); especially preferably, I, Br, Cl or OSO2CF3; and more preferably, I or Br.

[142] Among the compounds of formula (VIII): - M1 is a boronic acid, boronic acid alkyl ester, Sn-tri(C1-C4 alkyl); especially preferably, B(OH)2, B(O(C1-C10 alkyl))2 or Sn-tri(C1-C4 alkyl); and more preferably, BO2C2(CH3)4 (= “B-pin”) or Sn-tri(C1C4 alkyl).

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

[144] The reaction can, in principle, be conducted in substance. Preference is given, however, to the reaction of compounds of formula (VII) with compounds of formula (VIII) in organic solvent with or without water as co-solvent.

[145] Suitable solvents are those capable of dissolving the compounds of formula (VII) and the compounds of formula (VIII) at least partially and, preferably, completely under the reaction conditions.

[146] Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o, m and p-xylene; ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF); as well as bipolar aprotic solvents such as sulfolane, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolinone (DMI), N,N'-dimethylpropylene urea (DMPU) , dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP).

[147] Preferred solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF) and bipolar aprotic solvents such as sulfolane, N,N-dimethylformamide ( DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolinone (DMI), N,N'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP). Most preferred solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF). It is also possible to use mixtures of the mentioned solvents.

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

[149] 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 carbonates of alkali metals or alkaline earth metals, such as Li2CO3, Na2CO3, K2CO3, Cs2CO3, MgCO3 and CaCO3, and phosphates of alkaline earth metals such as K3PO4; and alkali and alkaline earth metal acetates, such as sodium acetate. Especially preferred bases are inorganic compounds, such as alkali and alkaline earth metal hydroxides, as well as 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.

[150] The term base, as used herein, also includes mixtures of two or more, preferably two of the above compounds. Specific preference is given to using a foundation. The bases are preferably used in 1 to 10 equivalents based on the compound of formula (VII), more preferably from 1.0 to 5.0 equivalents based on the compound of formula (VII), more preferably from 1.2 to 2.5 equivalents based on the compound of formula (VII).

[151] It may be advantageous to add the offset base over a period of time.

[152] The reaction of compounds of formula (VII) with compounds of formula (VIII) is conducted in the presence of a catalyst. Examples of suitable catalysts include, for example, palladium-based catalysts such as palladium(II) acetate, tetrakis(triphenylphosphine)-palladium(0), bis(triphenylphosphine)palladium(II) chloride or (1,1- bis(diphenylphosphine)-ferrocene)-dichloropalladium (II) and, optionally, appropriate additives such as phosphines such as, for example, P-(o-tolyl)3, triphenylphosphine or BINAP (2,2'-bis(diphenylphosphine)- 1,1'-binaphthyl). The amount of catalyst is normally 0.01 to 20 mol% (0.0001 to 0.2 equivalents) based on the compounds of formula (VII).

PROCESS AND

[153] Alternatively, depending on the nature of the Y group, pyridyl ethers of formula (I) can also be prepared through nucleophilic addition of compounds of formula (IX) to compounds of formula (VII):

[154] Among the compounds of formula (VII): L3 is a residual group such as halogen or OSO2CF3; especially preferably F, Cl or OSO2CF3; and more preferably, F or Cl.

[155] Among the compounds of formula (IX), M2 is magnesium halide, zinc halide, Li or Cu; of special preference, they are magnesium halide or Li.

[156] The reaction is normally carried out from -78 °C to the boiling point of the reaction mixture, preferably from -20 °C to 40 °C, in inert organic solvent.

[157] The reaction can, in principle, be conducted in substance. Preference is given, however, to the reaction of compounds of formula (VII) with compounds of formula (IX) in organic solvent.

[158] Suitable solvents are those capable of dissolving the compounds of formula (VII) and the compounds of formula (IX) at least partially and, preferably, completely under the reaction conditions.

[159] Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o, m and p-xylene; ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF); as well as bipolar aprotic solvents such as sulfolane, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolinone (DMI), N,N'-dimethylpropylene urea (DMPU) , dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP).

[160] Preferred solvents are ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF) and bipolar aprotic solvents such as sulfolane, N,N-dimethylformamide ( DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolinone (DMI), N,N'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP). Most preferred solvents are ethers such as diethyl ether, diisopropyl ether, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolinone (DMI), N,N '-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP). It is also possible to use mixtures of the mentioned solvents.

PROCESS F

[161] Alternatively, pyridyl ethers of formula (I), where Y is Y76, A1 is O, R14 is OH and R22 is H can also be prepared by reacting a compound of formula (XVIII) with isocyanate salt ( XXII) in the presence of acid (e.g. EP 1,095,935):

[162] In process F, the variables preferably have the following meanings: - A1 and A2 are O; - R12 is CF3; and - R13 and R22 are H.

[163] Consequently, pyridyl ethers of formula (I), wherein Y is Y76, A1 and A2 are O, R12 is CF3, R13 and R15 are H, R14 is OH and R22 is H, can be preferably prepared by means of reaction of compound of formula (XVIII), where A2 is O, R12 is CF3, R13 and R15 are H with an isocyanate salt (XXII) in the presence of acid (e.g. EP 1,095,935):

[164] The reaction of compounds of formula (XVIII) with the isocyanate salt (XXII) is normally carried out from -20 °C to the boiling point of the reaction mixture, preferably from 10 °C to 100 °C, in the presence of acid.

[165] Suitable isocyanate salts (XXII) are generally those salts of cations that do not have adverse effects on the reaction.

[166] Preferred cations are ions of alkali metals, preferably sodium and potassium, alkaline earth metals, preferably calcium and magnesium, and transition metals, preferably silver, copper and zinc, as well as ammonium and substituted ammonium , in which one to four hydrogen atoms are replaced by C1-C4 alkyl, C1-C4 hydroxyalkyl, C1-C4 alkoxy C1-C4 alkyl, C1-C4 hydroxyalkoxy C1-C4 alkyl, phenyl or benzyl, preferably tetraethylammonium and tetrabutylammonium.

[167] The term “salt(s)”, as used herein, also includes mixtures of two or more, preferably two of the above different salts. Specific preference is given to the use of a salt.

[168] Alkaline and alkaline earth metal isocyanates and, specifically, KOCN are preferred.

[169] In one embodiment of the process according to the present invention, the isocyanate salt (XXII) is used in excess quantity with respect to the compound of formula (XVIII).

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

[171] Preferably, the molar ratio between the isocyanate salt (XXII) and the compound of formula (XVIII) is in the range of 1:1 to 3:1, preferably 1:1 to 2:1 and, preferably special, 2:1.

[172] The reaction can, in principle, be conducted in substance. Preference is given, however, to the reaction of the compound of formula (XVIII) with the isocyanate salt (XXII) in organic solvent. In principle, all solvents that are capable of dissolving the compound of formula (XVIII) and the isocyanate salt (XXII) at least partially and, preferably, completely under the reaction conditions are suitable.

[173] Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8 alkanes, aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o, m and p-xylene, hydrocarbons halogenated compounds such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, 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 and cyclohexanone; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, bipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, 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-pyrrolidinone (NMP).

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

[175] The reaction of the compound of formula (XVIII) with the isocyanate salt (XXII) is conducted in the presence of acid.

[176] As acids and acid catalysts, mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and organic acids such as acetic acid, propionic acid, butyric acid, benzoic acid, methylbenzenesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid and methanesulfonic acid.

[177] Acids are generally used in equimolar amounts, but they can also be used in excess or, if appropriate, be used as solvents.

[178] The end of the reaction can be easily determined by those skilled in the art using routine methods.

[179] The reaction mixtures are worked up in the usual way, for example, by mixing with water, and optionally neutralizing, phase separation and, if appropriate, chromatographic purification of the crude product. 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 moderately elevated temperature. If the intermediates and final products are obtained in solid form, purification can also be conducted through recrystallization or digestion.

[180] By means of this process F, preferably pyridyl ethers (I.ak), specifically preferably the pyridyl ethers of formulas (I.ak.1) to (I.ak.36) as defined above, can be obtained from of the corresponding compounds of formula (XVIII.ak), wherein R1, R2, R3 and R4 are as defined above, preferably as defined in Table A above:

[181] The isocyanate salt (XXII) is preferably KOCN.

[182] Particularly preferably, the pyridyl ether of formula (I.ak.19) may be prepared from the corresponding compound of formula (XVIII.ak.19) in a manner analogous to process F mentioned above:

[183] The isocyanate salt (XXII) is preferably KOCN.

[184] Also preferably pyridyl ethers (I.al), specifically preferably the pyridyl ethers of formulas (I.al.1) to (I.al.36) as defined above, may be obtained from the corresponding compounds of the formula (XVIII.al), where R1, R2, R3 and R4 are as defined above, preferably as defined in Table A above:

[185] The isocyanate salt (XXII) is preferably KOCN.

[186] Particularly preferably, the pyridyl ether of formula (I.al.19) may be prepared from the corresponding compound of formula (XVIII.al.19) in a manner analogous to process F mentioned above:

[187] The isocyanate salt (XXII) is preferably KOCN.

[188] The intermediates necessary for the preparation of the pyridyl ethers of formula (I) according to the present invention and mentioned in processes A to F above are commercially available or can be prepared by standard organic chemistry processes, e.g. through the following processes.

[189] Pyridines of formula (II) (required for process A mentioned above) can be obtained from aminopyridines (XIX) analogously to process C or from pyridines (X) analogously to process D or E, depending of the nature of group Y as defined in processes C, D and E.

[190] Alternatively, pyridines of formula (II) can be prepared by reacting compounds of formula (X) with reagents of formula (XI) in the presence of base:

[191] Among the compounds of formula (X): - L4 is a residual group such as halogen, C1-C6 alkyl sulfonate or aryl sulfonate; preferably, F, Cl, C1-C6 alkyl sulfonate or aryl sulfonate; - especially preferably, F, Cl, OSO2CH3 or OSO2C6H4CH3; and - more preferably, F or Cl.

[192] Compounds of formula (III) necessary in process A for the preparation of pyridyl ethers of formula (I) are commercially available or known from the literature.

[193] Compounds of formula (IV) (required for process B mentioned above) can be prepared by deprotecting the corresponding compounds of formula (XII):

[194] Among the compounds of formula (XII): “PG” is a protecting group selected from the group consisting of 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, (C1-C6 trialkyl)C1-C4 silylalkyl, (C1-C6 trialkyl)C1-C4 silylalkyloxy C1-C4 alkyl, alkenyl C2-C6, C3-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1C4 alkyl, C5-C6 cycloalkenyl, tetrahydropyranyl, (C1-C6 trialkyl)silyl, [(diphenyl)(C1-C4 alkyl)]silyl , formyl, C1-C6 alkylcarbonyl, C1-C6-alkyl-O-carbonyl, C2-C6-O-alkenyl, [(diphenyl)(C1-C4 alkyl)]C1-C4 silylalkyl, C1-C4 phenylalkyl, C1- phenylthioalkyl C6 is phenylcarbonyl; wherein each phenyl ring may be replaced by one to three substituents selected from the group consisting of halogen, CN, NO2, C1-C4 alkyl and C1-C4 alkoxy; Preferably, PG is C1-C6 alkyl, C1-C6 alkoxy C1-C4 alkyl, (C1-C6 trialkyl)C1-C4 silylalkyl, C2-C6 alkenyl, tetrahydropyranyl, (C1-C6 trialkyl)silyl, [(diphenyl) (C1-C4 alkyl)]silyl or C1-C4 phenylalkyl.

[195] Compounds of formula (IV) can be prepared, for example, by treating compounds of formula (XII), where “PG” is methyl, with boron tribromide in a solvent such as dichloromethane, acetonitrile or 1 ,4-dioxane, or without solvent at temperatures ranging from 0 °C to 150 °C.

[196] Alternatively, compounds of formula (IV) can be prepared by deprotecting compounds of formula (XII), where “PG” is a benzyl group, by catalytic hydrogenation in a hydrogen gas atmosphere under pressure of 70 at 700 kPa, preferably 270 to 350 kPa, in the presence of a metallic catalyst such as palladium supported on an inert vehicle such as activated carbon, in a weight ratio of 5 to 20% between metal and vehicle, suspended in a solvent such as ethanol at room temperature.

[197] The use and selection of protecting groups will be evident to those skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M., Protective Groups in Organic Synthesis, 4th Ed.; Wiley: New York, 2007) .

[198] Alkylating agents of formula (V) (necessary for process B mentioned above) are commercially available or known in the literature.

[199] Compounds of formula (VI) (required for process C mentioned above) can be obtained from the corresponding pyridines of formula (XIII):

[200] Among the pyridines of formula (XIII), the “PGN” group is a protected amine substituent selected from the group consisting of N3, aliphatic or aromatic carbamates, aliphatic or aromatic amides, N-C1-C6 alkylamines, N -arylamines or heteroarylamides.

[201] Preferably, PGN is selected from the group consisting of N3, C1-C6 alkyl-O(CO)NH-, C1-C6 haloalkyl-O(CO)-NH-, (C1-C6 trialkyl)-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 alkyl -C6)-N-, (C1-C6 alkyloxy C1-C4 alkyl)NH-, di(C1-C6 alkyloxy C1-C4 alkyl)N-, C2-C6 alkenyl-NH, di(C2-C6 alkenyl)N- , (C1-C4 trialkyl)-Si-C1-C4 alkoxy-C1-C4 alkyl-NH-, di[(C1-C4 trialkyl)-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-, phenylalkyl C1- C4-O(CO)NH-, phenyl-(CO)NH-, phenylC1-C6alkyl-(CO)NH-, pyridyl-(CO)-NH-, ortho-(C1-C4 alkoxy)-phenyl-NH, di[ortho-(C1-C4 alkoxy )-phenyl]N-, para-(C1-C4 alkoxy)-phenyl-NH, di[para-(C1-C4 alkoxy)-phenyl]N-, phenylC1-C4 alkyl-NH-, di(phenylC1-C4 alkyl )N-, para-(C1-C4 alkoxy)-phenyl C1-C4 alkyl-NH and di[para-(C1-C4 alkoxy)-phenyl C1-C4 alkyl]N-; wherein each phenyl or pyridyl ring may be replaced by one to three substituents selected from the group consisting of halogen, CN, NO2, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylsulfinyl and C1C4 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-, C1-C4 phenylalkyl-O(CO)NH-, C1-C4 phenylalkyl-NH- and di( C1-C4)N-phenylalkyl; wherein each phenyl or pyridyl ring can be replaced by one to three C1-C4 alkoxy substituents.

[202] If “PGN” is an azide substituent, the pyridines of formula (XIII) can be converted to the amine of formula (VI) using reducing reaction conditions, such as zinc in an aqueous ammonium chloride solution.

[203] If “PGN” is an acylated amine substituent, the pyridines of formula (XIII) can be converted to the amines of formula (VI) using acid.

[204] The use and selection of the “PGN” substituent and appropriate deprotection methods will be evident to those skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M., Protective Groups in Organic Synthesis, 4th Ed.; Wiley: New York, 2007).

[205] The compounds of formula (VII) necessary for the preparation of pyridyl ethers of formula (I) can be prepared by reacting pyridines of formula (XIV) with compounds of formula (III) in the presence of base, in a similar way to process A:

[206] Among the pyridines of formula (XIV): - L1 is a residual group such as halogen, C1-C6 alkyl sulfonate or aryl sulfonate; preferably, F, Cl, C1-C6 alkyl sulfonate or aryl sulfonate; especially preferably, F, Cl, OSO2CH3 or OSO2C6H4CH3; and more preferably, F or Cl; - L3 is a residual group such as halogen or OSO2CF3; especially preferably F, Cl or OSO2CF3; and more preferably, F or Cl.

[207] Alternatively, compounds of formula (VII) necessary for preparing pyridyl ethers of formula (I) can be prepared by reacting pyridines of formula (XV) with compounds of formula (V) in the presence of base, so analogous to process B:

[208] Among the pyridines of formula (XV): L3 is a residual group such as halogen or OSO2CF3; especially preferably F, Cl or OSO2CF3; and more preferably, F or Cl.

[209] Boronic acid, alkyl esters of boronic acid or Sn-tri(C1-C4 alkyl) of formula (VIII) necessary for preparing compounds of formula (I) in process D are commercially available, known in the literature or easily prepared from from the corresponding compounds where M1 = Cl, Br or I.

[210] Compounds of formula (IX) necessary for preparing pyridyl ethers of formula (I) in process E are commercially available, known in the literature or easily prepared from the corresponding compounds in which M2 = Cl, Br or I.

[211] Compounds of formula (X) necessary for the preparation of pyridines of formula (II) are commercially available or known in the literature.

[212] Compounds of formula (XI) necessary for the preparation of pyridines of formula (II) are commercially available or known in the literature.

[213] The compounds of formula (XII) necessary for preparing the compounds of formula (IV) mentioned above can be prepared by reacting pyridines of formula (II) with compounds of formula (XVI) in the presence of base, so analogous to processes A and B mentioned above:

[214] Among the compounds of formula (XVI), the “PG” group is a protecting group as defined above for compounds of formula (XII).

[215] Pyridines of formula (XIII) (necessary for preparing the amines of formula (VI) mentioned above) can be prepared by reacting compounds of formula (XVII) with compounds of formula (III) (necessary for process A mentioned above) in the presence of base, in a manner analogous to process A mentioned above:

[216] Among the compounds of formula (XVii), L5 is a residual group such as halogen, C1-C6 alkyl sulfonate or aryl sulfonate; preferably, F, Cl, C1-C6 alkyl sulfonate or aryl sulfonate; especially preferably, F, Cl, OSO2CH3 or OSO2C6H4CH3; more preferably, F or Cl.

[217] Among the compounds of formula (XVII), the “PGN” group is a protected amine substituent as defined above for the amines of formula (Xiii).

[218] Compounds of formula (XiV) necessary for the preparation of compounds of formula (Vii) are commercially available or known in the literature.

[219] Pyridines of formula (XV) necessary for the synthesis of compounds of formula (Vii) can be prepared by reacting pyridines of formula (XiV) with compounds of formula (XVi) in the presence of base and subsequent deprotection:

[220] Among the compounds of formula (XVI), the “PG” group is a protecting group as defined above for compounds of formula (Xii). The use and selection of the appropriate protecting group and deprotection methods will be apparent to those skilled in chemical synthesis (see, e.g., Greene, T.W.; Wuts, P.G.M., Protective Groups in Organic Synthesis, 4th Ed.; Wiley: New York, 2007).

[221] Compounds of formula (XVII) necessary for the synthesis of pyridines of formula (XII) are commercially available or known in the literature.

[222] Pyridines of formula (XV) (required for the preparation of compounds of formula (XVII) mentioned above) are commercially available or can be prepared by known methods from the corresponding amine (e.g., Greene, T. W.; Wuts , P. G. M., Protective Groups in Organic Synthesis, 4th ed.; Wiley: New York, 2007).

[223] Compounds of formula (XVIII) (required for the process F mentioned above) can be obtained from the corresponding amines of formula (XIX) with compounds of formula (XX) (for example, EP 1,095,935):

[224] L6 in the compound of formula (XX) is a residual group such as C1-C6 alkoxy or aryloxy, preferably C1-C6 alkoxy and, especially preferably, OCH3 or OC2H6.

[225] The reaction of the amines of formula (XIX) with the compound of formula (XX) is normally conducted from room temperature to the boiling point of the reaction mixture.

[226] The reaction can, in principle, be conducted in substance. Preference is given, however, to the reaction of the amine of formula (XIX) with the compound of formula (XX) in organic solvent. In principle, all solvents are suitable that are capable of dissolving the amine of formula (XIX) and the compound of formula (XX), at least partially and, preferably, completely under reaction conditions.

[227] Examples of suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8 alkanes; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- 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), dioxane, anisole and tetrahydrofuran (THF); nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone, tert-butyl methyl ketone and cyclohexanone; alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol; and bipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, 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-pyrrolidinone (NMP).

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

[229] The alcohol byproduct can be distilled from the reaction mixture or a small amount of an acid (such as p-toluenesulfonic acid and methanesulfonic acid) or a base (e.g., triethylamine, pyridine, potassium carbonate or sodium hydride) can be added to speed up the reaction.

[230] The end of the reaction can be easily determined by those skilled in the art using routine methods.

[231] Reaction mixtures are worked up in a customary manner, for example, by mixing with water, neutralization, phase separation and, if appropriate, chromatographic purification of the crude product. 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 moderately elevated temperature. If the intermediates and final products are obtained in solid form, purification can also be conducted through recrystallization or digestion.

[232] By means of a side reaction of the compounds of formula (XVIII), in which R15 is H, with the amine of formula (XIX), the following dimer of formula (XXI) can also be obtained:

[233] In a similar way to what was described above, the dimer (XXI.ak.19) can be obtained by reacting the amine of the formula (XIX.ak.19) with the compound of the formula (XVIII.ak.19):

[234] In a similar way, the dimer (XXI.al.19) can be obtained by reacting the amine of the formula (XIX.al.19) with the compound of the formula (XVIII.al.19):

[235] Amines of formula (XIX) (necessary for preparing compounds of formula XVIII) can be obtained in a manner analogous to the process described in WO 17/202768 for amines of formula (XI).

[236] Compounds of formula (XX) are commercially available.

[237] Isocyanate salts (XXII) are commercially available.

[238] To broaden the spectrum of action and achieve synergistic effects, the pyridyl ethers of formula (I) can be mixed with a large number of representatives from other groups of herbicidal or growth-regulating active ingredients and then applied simultaneously. Suitable components for mixtures are, for example, herbicides from the classes of acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoic acids, benzothidiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoramidates, phosphorodithioates, phthalamates, pyrazoles, , pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones , pyrimidinyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils and ureas.

[239] It may also be beneficial to apply the pyridyl ethers of formula (I) alone or in combination with other herbicides, or even in the form of a mixture with other crop protection agents, such as in conjunction with pest control agents or phytopathogenic bacteria or fungi. Also of interest is the miscibility with mineral salt solutions that are used to treat nutritional and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates can also be added.

[240] In an embodiment of the present invention, the compositions according to the present invention comprise at least one pyridyl ether of formula (I) (compound A) and at least one additional active compound selected from herbicides B, preferably herbicides B from class b1 to b15, and security officers C (compound C).

[241] In another embodiment of the present invention, the compositions according to the present invention comprise at least one pyridyl ether of formula (I) and at least one additional active compound B (herbicide B).

[242] The additional herbicidal compound B (component B) is preferably selected from herbicides of class b1 to b15: b1. lipid biosynthesis inhibitors; b2. acetolactate synthase inhibitors (ALS inhibitors); b3. photosynthesis inhibitors; b4. protoporphyrinogen-IX oxidase inhibitors: b5. bleaching herbicides; b6. enolpyruvyl synthase shikimate 3-phosphate inhibitors (EPSP inhibitors): b7. glutamine synthetase inhibitors; b8. 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); b9. mitosis inhibitors; b10. very long chain fatty acid synthesis inhibitors (VLCFA inhibitors); b11. cellulose biosynthesis inhibitors; b12. uncoupling herbicides; b13. auxin herbicides; b14. auxin transport inhibitors; and b15. other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumiluron, dalapon, dazomet, diphenzoquat, diphenzoquat methylsulfate, dimetipin, DSMA, dimron, endotal and its salts, etobenzanid, flamprop, flamprop-isopropyl , flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanophan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7 ), methyl azide, methyl bromide, methyl-dimron, methyl iodide, MSMA, oleic acid, oxaziclomephone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy) -4-pyridazinol (CAS 499223-49-3), its salts and esters; including its salts or agricultural derivatives.

[243] Preference is given to compositions according to the present invention that comprise at least one herbicide B selected from herbicides of class b2, b3, b4, b5, b6, b7, b9, b10 and b13.

[244] Specific preference is given to compositions according to the present invention that comprise at least one B herbicide selected from herbicides of class b4, b6, b7, b9, b10 and b13.

[245] Specific preference is given to compositions according to the present invention that comprise at least one B herbicide selected from class b4, b6, b10 and b13 herbicides.

[246] Examples of B herbicides that can be used in combination with the pyridyl ethers of formula (I) according to the present invention are: b1. from the group of lipid biosynthesis inhibitors: - ACC herbicides, such as aloxidim, aloxidim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxidim, ci-halofop, ci-halofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxidim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuril, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuril, sethoxydim, tepraloxidim, tralkoxidim, 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-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6, 6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6 -tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6, 6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6- tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- acid methyl ester carbonic tetramethyl-5-oxo-2H-pyran-3-yl (CAS 131233751-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl acid methyl ester carbonic -5-oxo-2H-pyran-3-yl; 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- acid methyl ester carbonic tetramethyl-5-oxo-2H-pyran-3-yl (CAS 1312340-83-2); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-acid methyl ester carbonic 5-oxo-2H-pyran-3-yl (CAS 1033760-58-5); and non-ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, etofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, tiobencarb, thiocarbazil, triallate and vernolate; b2. from the group of ALS inhibitors: - sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cynosulfuron, cyclosulfamuron, etametsulfuron, etametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupirsulfuron, - methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, ron, primisulfuron-methyl, propyrisulfuron, 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 imazametabenzo, imazametabenzo-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides, such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florassulam, metosulam, penoxsulam, pyrimisulfan and pyroxs ulam; - pyrimidinyl benzoates, such as bispiribac, bispiribac-sodium, pyribenzoxim, pyriftalid, piriminobac, pyriminobac-methyl, pyritiobac, pyrithiobac-sodium, 1-methylethyl ester of 4-[[[2-[(4,6-dimethoxy-acid) 2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl] acid propyl ester methyl]amino]-benzoic acid (CAS 420138-40-5) and N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 4201318-01-8); and - sulfonylaminocarbonyltriazolinone herbicides, such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone; Among these, a preferred embodiment of the present invention relates to compositions comprising at least one imidazolinone herbicide; b3. from the group of photosynthesis inhibitors: - amicarbazone, photosystem II inhibitors, such as 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrole-5-one (CAS 1637455-12-9) , 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert- butyl-1-methylpyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrole-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1- methylpyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrole-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 (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1- methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785- 80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3 -methylimidazolidin-2-one (CAS 1844836-64-1), triazine herbicides, including chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones such as amethrin, atrazine, chloridazone, cyanazine, desmethrin, dimethethrin, hexazinone, metribuzin, prometon, promethrin , propazine, simazine, simetrin, terbumeton, terbuthylazin, terbutrin and trietazin, aryl urea such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, metabenzotiazuron, metobenzuron, methoxuron, monolinuron, neburon, siduron , tebuthiuron and thiadiazuron, phenyl carbamates such as desmedifam, carbutilat, phenmedifam, phenmedifam-ethyl, nitrile herbicides such as bromophenoxim, bromoxynil, their salts and esters, ioxynil, their salts and esters, uracils such as bromacil, lenacil and terbacil, bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor, propanil and photosystem I inhibitors such as diquat, diquat paraquat dibromide, paraquat dichloride and paraquat dimethylsulfate. Among these, a preferred embodiment of the present invention relates to compositions comprising at least one aryl urea herbicide. Among these, similarly, a preferred embodiment of the present invention relates to compositions comprising at least one triazine herbicide. Among these, similarly, a preferred embodiment of the present invention relates to compositions comprising at least one nitrile herbicide; b4. from the group of protoporphyrinogen IX oxidase inhibitors: - acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzofendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, clomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufempir, flufempir-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, flutiacet, flutiacet-methyl, medosafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, tidiazimin, thiafenacil, trifludimoxazin, [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy Ethyl ]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazol-1- carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2 -chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2- inyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin- 6-yl)-4,5,6,7-tetrahydroisoindol-1,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro- 3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05- 0), (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methylpyrazol-3-yl]-4-fluorophenoxy]-3-methyl methoxybut-2-enoate (CAS 948893-00-3) and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2 ,4-dione (CAS 212754-02-4); preferably, acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzofendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, clomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufempir, flufempir-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycophen-ethyl, flutiacet, flutiacet-methyl, medosafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, tidiazimin, tiafenacil, trifludimoxazin, [3- [2- ethyl 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; tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6 -fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)- 5-methyl-1H-pyrazol-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H -benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-( 2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7 -tetrahydroisoindole-1,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl- 3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), (E)-4-[2- methyl chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methylpyrazol-3-yl]-4-fluorophenoxy]-3-methoxybut-2-enoate (CAS 948893-00-3) and 3-[ 7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4) ; b5. from the group of bleaching herbicides: - PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flutamone, norflurazon, picolinafen and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibition , amitrol, flumeturon, 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 136113971-0), 2-(2,4-dichlorophenyl)methyl-4 ,4-dimethyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7); b6. from the group of EPSP synthase inhibitors: - glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate); b7. from the group of glutamine synthase inhibitors: - bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammonium; b8. from the group of DHP synthase inhibitors DHP: - assulam; b9. from the group of mitosis inhibitors: - compounds of the K1 group: dinitroanilines, such as benfluralin, butralin, dinitramine, etalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as amiprophos, amiprophos-methyl and butamiphos, benzoic acid herbicides such as chlorthal, chlorthal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds from the K2 group: carbetamide, chlorprofam, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and profam; among these, compounds of the K1 group, particularly dinitroanilines, are preferred; b10. from the group of VLCFA inhibitors: - chloroacetamides, such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, petoxamid, pretilachlor, propachlor, propisochlor and tenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as difenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such as fentrazamide and other herbicides such as anilophos compounds, cafenstrol, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline of formulas II.1, II.2 , II.3, II.4, II.5, II.6, II.7, II.8 and II.9: Isoxazoline compounds of formula (I)I are known in the art, for example, from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576; Among VLCFA inhibitors, preference is given to chloroacetamides and oxyacetamides; b11. from the group of cellulose biosynthesis inhibitors: - chlorthiamid, diclobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorophenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1); b12. from the group of uncoupling herbicides: - dinoseb, dinoterb, DNOC and their salts; b13. from the group of auxinic herbicides: - 2,4-D and its salts and esters, such as claciphos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts, such as aminopyralid-dimethylammonium , aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid 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-butomethyl, fluroxypyr-meptyl, halauxifen and their salts and esters (CAS 943832-60-8); 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, florpirauxifen, florpirauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro- 1H-indol-6-yl)picolinic (CAS 1629965-65-6); b14. from the group of auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium; b15. from the group of other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumiluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, diphenzoquat, diphenzoquat methylsulfate, dimetipin, DSMA, dimron, endotal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanophan, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dimron, methyl iodide, MSMA, oleic acid, oxaziclomephone, pelargonic acid, piributicarb, quinoclamine and tridiphane.

[247] Active compounds B and C that contain a carboxyl group can be used in the form of the acid, in the form of an agriculturally appropriate salt as mentioned above or in the form of an agriculturally acceptable derivative in the compositions according to the present invention.

[248] In the case of dicamba, agriculturally useful salts include those in which the counterion is an agriculturally acceptable cation. Suitable dicamba salts are, for example, dicamba-sodium, dicamba-potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicambatrolamine, dicamba-N,N -bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of suitable esters are dicamba-methyl and dicamba-butotyl.

[249] 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-tris(2-hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D -lithium, 2,4-D-sodium and 2,4-D-N,N,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-tris(2-hydroxypropyl)ammonium, 2,4-D -tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium and 2,4-D-sodium. Examples of suitable 2,4-D esters are 2,4-D-butoxypropyl, 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-iso-octyl, 2,4-D-isopropyl, 2,4-D-methyl, 2 ,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and claciphos.

[250] Suitable 2,4-DB salts are, for example, 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dimethylammonium. Suitable 2,4-DB esters are, for example, 2,4-DB-butyl and 2,4-DB-iso-octyl.

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

[252] Suitable MCPA salts and esters include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-iso- octyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.

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

[254] Suitable clopyralid salts are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2-hydroxypropyl)ammonium. An example of suitable clopyralid esters is clopyralid-methyl.

[255] Examples of suitable fluroxypyr esters are fluroxypyr-methyl and fluroxypyr-2-butoxy-1-methylethyl, where fluroxypyr-methyl is preferred.

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

[257] A suitable triclopyr salt is triclopyr-triethylammonium. Suitable triclopyr esters are, for example, triclopyrethyl and triclopyrbutoyl.

[258] Suitable chloramben salts and esters 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.

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

[260] Suitable glyphosate salts are, for example, glyphosate-ammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium and also the salts of ethanolamine and diethanolamine, preferably glyphosate -diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate).

[261] Suitable glufosinate salt is, for example, glufosinate-ammonium.

[262] Suitable glufosinate-P salt is, for example, glufosinate-P-ammonium.

[263] Suitable bromoxynyl salts and esters are, for example, bromoxynyl butyrate, bromoxynyl heptanoate, bromoxynyl octanoate, bromoxynyl-potassium and bromoxynyl-sodium.

[264] Suitable ioxonyl salts and esters are, for example, ioxonyl octanoate, ioxonyl-potassium and ioxonyl-sodium.

[265] Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-iso-octyl, mecoprop-methyl, mecoprop-potassium, mecoprop- sodium and mecoproptrolamine.

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

[267] Suitable diflufenzopyr salt is, for example, diflufenzopyrsodium.

[268] A suitable naptalam salt is, for example, naptalam sodium.

[269] Suitable aminocyclopyraclor salts and esters are, for example, aminocyclopyraclor-dimethylammonium, aminocyclopyraclor-methyl, aminocyclopyraclor-triisopropanolammonium, aminocyclopyraclor-sodium and aminocyclopyraclor-potassium.

[270] Suitable quinclorac salt is, for example, quinchlorac-dimethylammonium.

[271] Suitable quinmerac salt is, for example, quinmerac-dimethylammonium.

[272] Suitable imazamox salt is, for example, imazamox-ammonium.

[273] Suitable imazapic salts are, for example, imazapic-ammonium and imazapic-isopropylammonium.

[274] Suitable imazapyr salts are, for example, imazapyr-ammonium and imazapyr-isopropylammonium.

[275] A suitable imazaquin salt is, for example, imazaquin-ammonium.

[276] Suitable imazethapyr salts are, for example, imazethapyr-ammonium and imazethapyr-isopropylammonium.

[277] Suitable topramezone salt is, for example, topramezone-sodium.

[278] Particularly preferred B herbicides are the B herbicides defined above; particularly, the herbicides B.1-B.203 and, preferably, the herbicides B.1-B.202 listed in Table B. TABLE B

[279] Furthermore, it may be useful to apply the pyridyl ethers of formula (I) in combination with safety agents. Safety agents are chemical compounds that prevent or reduce damage to useful plants without causing a greater impact on the herbicidal action of pyridyl ethers of formula (I) on unwanted plants. They can be applied before crops (e.g. in seed, sprout or seedling treatments) or in pre-emergence or post-emergence application of the useful plant. The safety agents and pyridyl ethers of formula (I) and, optionally, herbicides B can be applied simultaneously or successively.

[280] In another embodiment of the present invention, the compositions according to the present invention comprise at least one pyridyl ether of formula (I) and at least one safety agent C (component C).

[281] Suitable safety agents are, for example, (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3-carboxylic acids, 1-phenyl- 4,5-dihydro-5-alkyl-1H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oxyminophenylacetonitrile, acetophenonoximes, 4 ,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5- acids thiazolecarboxylic acids, phosphorothiolates and N-alkyl-O-phenylcarbamates, their agriculturally acceptable salts and their agriculturally acceptable derivatives, such as amides, esters and thioesters, provided that they contain an acidic group.

[282] Examples of preferred safety agents C are benoxacor, cloquintocet, ciometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazol, fluxfenim, furilazole, isoxadifen, mefempir, mefenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl )-1-oxa-4- azaspiro[4.5]decane (MON4660 and CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS 52836 -31-4), metcamifen (CAS 129531-12-0) and BPCMS.

[283] Particularly preferred security agents C which, as component C, are components of the composition according to the present invention are the security agents C defined above; particularly, the security officers C.1-C.17 listed below in Table C.TABLE C

[284] Active compounds B of groups b1 to b15 and active compounds C are known herbicides and safety agents; see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000, volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement to the 7th Edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS No. 52836-31-4) it is also called R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS No. 71526-07-3) is also called AD-67 and MON 4660.

[285] The assignment of active compounds to corresponding mechanisms of action is based on current knowledge. If several mechanisms of action apply to an active compound, that substance was assigned to only one mechanism of action.

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

[287] According to another preferred embodiment of the present invention, the composition comprises, as herbicide active compound B or component B, at least two, preferably exactly two herbicides B different from each other.

[288] According to another preferred embodiment of the present invention, the composition comprises, as herbicide active compound B or component B, at least three, preferably exactly three different herbicides B.

[289] According to another preferred embodiment of the present invention, the composition comprises, as herbicide active compound B or component B, at least four, preferably exactly four different herbicides B.

[290] According to another preferred embodiment of the present invention, the composition comprises a security component C or component C, at least one, preferably exactly one security agent C.

[291] According to another preferred embodiment of the present 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 safety agent C.

[292] According to another preferred embodiment of the present invention, the composition comprises at least two, preferably exactly two different B herbicides and, as component C, at least one, preferably exactly one C safety agent.

[293] According to another preferred embodiment of the present invention, the composition comprises at least three, preferably exactly three different B herbicides and, as component C, at least one, preferably exactly one C safety agent.

[294] 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 of formula (I.a), (I.b), (I.e), ( I.l), (I.m), (I.n), (I.o), (I.p), (I.q), (I.s), (I.t), (I.w), (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.

[295] 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 of formula (I.a), (I.b), (I.e), ( I.l), (I.m), (I.n), (I.o), (I.p), (I.q), (I.s), (I.t), (I.w), (I.ac), (I.ad), (I. ae), (I.af), (I.ag) or (I.ah) and at least two, preferably exactly two different B herbicides.

[296] 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 of formula (I.a), (I.b), (I.e), ( I.l), (I.m), (I.n), (I.o), (I.p), (I.q), (I.s), (I.t), (I.w), (I.ac), (I.ad), (I. ae), (I.af), (I.ag) or (I.ah) and at least three, preferably exactly three different B herbicides.

[297] 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 of formula (I.a), (I.b), (I.e), ( I.l), (I.m), (I.n), (I.o), (I.p), (I.q), (I.s), (I.t), (I.w), (I.ac), (I.ad), (I. ae), (I.af), (I.ag) or (I.ah) and at least four, preferably exactly four different B herbicides.

[298] 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 of formula (I.a), (I.b), (I.e), ( I.l), (I.m), (I.n), (I.o), (I.p), (I.q), (I.s), (I.t), (I.w), (I.ac), (I.ad), (I. ae), (I.af), (I.ag) or (I.ah) and, as a C component, at least one, preferably exactly one C security agent.

[299] 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 of formula (I.a), (I.b), (I.e), ( I.l), (I.m), (I.n), (I.o), (I.p), (I.q), (I.s), (I.t), (I.w), (I.ac), (I.ad), (I. ae), (I.af), (I.ag) or (I.ah), as component B, at least one, preferably exactly one herbicide B and, as component C, at least one, preferably exactly one agent security C.

[300] 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 of formula (I.a), (I.b), (I.e), ( I.l), (I.m), (I.n), (I.o), (I.p), (I.q), (I.s), (I.t), (I.w), (I.ac), (I.ad), (I. ae), (I.af), (I.ag) or (I.ah), at least two, preferably exactly two different B herbicides and, as component C, at least one, preferably exactly one security C.

[301] 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 of formula (I.a), (I.b), (I.e), ( I.l), (I.m), (I.n), (I.o), (I.p), (I.q), (I.s), (I.t), (I.w), (I.ac), (I.ad), (I. ae), (I.af), (I.ag) or (I.ah), at least three, preferably exactly three different B herbicides and, as component C, at least one, preferably exactly one security C.

[302] According to another preferred embodiment of the present invention, the composition comprises, in addition to a pyridyl ether of formula (I), especially an active compound from the group consisting of (I.a.18), (I.a.19), (I.e.18), (I.e.19), (I.l.18), (I.l.19), (I.n.18), (I.n.19), (I.o.18), (I.o.19), (I.q.18), (I.q.19), (I.s.18), (I.s.19), (I.w.18), (I.w.19), (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 and especially exactly one compound active as a herbicide of group b4, particularly selected from from the group consisting of acifluorfen, butafencil, carfenetrazone-ethyl, flumioxazin, medosafen, oxadiargyl, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, [3-[2-chloro-4-fluoro-5-(1- ethyl methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100) .

[303] According to another preferred embodiment of the present invention, the composition comprises, in addition to a pyridyl ether of formula (I), especially an active compound from the group consisting of (I.a.18), (I.a.19), (I.e.18), (I.e.19), (I.l.18), (I.l.19), (I.n.18), (I.n.19), (I.o.18), (I.o.19), (I.q.18), (I.q.19), (I.s.18), (I.s.19), (I.w.18), (I.w.19), (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 and especially exactly one compound active as a herbicide of group b6, particularly selected from from the group consisting of glyphosate, glyphosate-ammonium, glyphosate-dimethylammonium, glyphosate-isopropylammonium, glyphosate-trimesium (sulfosate) and glyphosate-potassium.

[304] According to another preferred embodiment of the present invention, the composition comprises, in addition to a pyridyl ether of formula (I), especially an active compound from the group consisting of (I.a.18), (I.a.19), (I.e.18), (I.e.19), (I.l.18), (I.l.19), (I.n.18), (I.n.19), (I.o.18), (I.o.19), (I.q.18), (I.q.19), (I.s.18), (I.s.19), (I.w.18), (I.w.19), (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 and especially exactly one compound active as a herbicide of group b10, particularly selected from from the group consisting of acetochlor, butachlor, cafenstrol, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazaclor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone. Similarly, preference is given to compositions comprising, in addition to a pyridyl ether of formula (I), especially an active compound from the group consisting of (I.a.18), (I.a.19), (I.e.18), (I.e. 19), (I.l.18), (I.l.19), (I.n.18), (I.n.19), (I.o.18), (I.o.19), (I.q.18), (I.q.19), (I.s.18), (I.s. 19), (I.w.18), (I.w.19), (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 and especially exactly one herbicide-active compound of group b10, particularly selected from group which consists of isoxazoline compounds of formulas II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, as defined above.

[305] According to another preferred embodiment of the present invention, the composition comprises, in addition to a pyridyl ether of formula (I), especially an active compound from the group consisting of (I.a.18), (I.a.19), (I.e.18), (I.e.19), (I.l.18), (I.l.19), (I.n.18), (I.n.19), (I.o.18), (I.o.19), (I.q.18), (I.q.19), (I.s.18), (I.s.19), (I.w.18), (I.w.19), (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 and especially exactly one compound active as a herbicide of group b13, particularly selected from from the group consisting of 2,4-D, 2,4-D-isobutyl, 2,4-D-dimethylammonium, 2,4-D-N,N,N-trimethylethanolammonium, aminocyclopyraclor, aminocyclopirachlor-potassium, aminocyclopirachlor-methyl, aminopyralid , aminopyralid-methyl, aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium, clopyralid, clopyralid-methyl, clopyralid-olamine, dicamba, dicamba-butotyl, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium , dicamba-potassium, dicamba-sodium, dicamba-trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine, dicamba-diethylenetriamine, flopyrauxifen, fluroxypyr, fluroxypyr-meptyl, halauxifen, halauxifen-methyl, MCPA, MCPA- 2-ethylhexyl, MCPA-dimethylammonium, quinclorac, quinclorac-dimethylammonium, quinmerac, quinmerac-dimethylammonium, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6 acid -(7-fluoro-1H-indol-6-yl)picolinic acid.

[306] Here and below, the expression “binary compositions” includes compositions comprising one or more, such as 1, 2 or 3 active compounds of formula (I) and one or more, such as 1, 2 or 3 herbicides B or one or more security officers C.

[307] Consequently, the expression “ternary compositions” includes compositions comprising one or more, such as 1, 2 or 3 active compounds of formula (I) and one or more, such as 1, 2 or 3 B herbicides or one or more, such as 1, 2 or 3 security officers C.

[308] In binary compositions comprising at least one compound of formula (I) as component A and at least one herbicide B, the weight ratio of active compounds A:B is generally in the range of 1:1,000 to 1,000: 1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, more specifically, in the range of 1:125 to 125:1.

[309] In binary compositions comprising at least one compound of formula (I) as component A and at least one safety agent C, the weight ratio of active compounds A:C is generally in the range of 1:1,000 to 1,000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, more specifically, in the range of 1:75 to 75:1.

[310] In ternary compositions comprising at least one pyridyl ether of formula (I) as component A, at least one herbicide B and at least one safety agent C, the relative parts by weight of components A:B are generally found in the range of 1:1,000 to 1,000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, more specifically, in the range of 1:125 to 125:1 ; the weight ratio of the A:C components is generally in the range of 1:1,000 to 1,000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, of specific preference, in the range of 1:75 to 75:1; and the weight ratio of the B:C components is generally in the range of 1:1,000 to 1,000:1, preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, preferably specific, in the range of 1:75 to 75:1. The weight ratio between components A+B and component C is preferably in the range of 1:500 to 500:1, particularly in the range of 1:250 to 250:1 and, more specifically, in the range of 1:75. to 75:1.

[311] The weight ratios of the individual components in the preferred mixtures mentioned below are within the limits provided herein, particularly within the preferred limits.

[312] Particularly preferred are the compositions mentioned below which comprise the pyridyl ethers of formula (I) as defined and the substance(s) defined in the corresponding line of Table 1; especially preferably, they comprise, as the only compounds active as herbicides, the pyridyl ethers of formula (I) as defined and the substance(s) defined in the corresponding line of Table 1; and preferably higher, comprise, as the only active compounds, the pyridyl ethers of formula (I) as defined and the substance(s) defined in the corresponding line of Table 1.

[313] Particularly preferred are compositions 1.1 to 1.3671, especially compositions 1.1 to 1.3653 comprising pyridyl ether (I.a.18) and the substance(s) defined in the corresponding line of Table 1. TABLE 1

[314] Compositions 1.1 to 1.3671:

[315] The specific number of each isolated composition can be deduced as follows:

[316] Composition 1,200 comprises, for example, pyridyl ether I.a.18 and cinmethylin (B.200) (see Table 1, line 1.200; as well as Table B, line B.200).

[317] Composition 2.200 comprises, for example, pyridyl ether I.a.19 (see the definition of compositions 2.1 to 2.3671, preferably 2.1 to 2.3653 below) and cinmethylin (B.200) (see Table 1, line 1.200; as well as Table B, line B.200).

[318] Also of special preference are Compositions 2.1 TO 2.3671, Preferably 2.1 TO 2.3653, Which Differ From Corresponding Compositions 1.1 TO 1.3671, Preferably 1.1 TO 1.3653, Only Because They Comprise, As Active Compound A, The Pyridyl Ether Of Formula (I.A.19 ).

[319] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.e.18 ).

[320] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.e.19 ).

[321] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.l.18 ).

[322] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.l.19 ).

[323] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.n.18 ).

[324] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.n.19 ).

[325] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.o.18 ).

[326] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.o.19 ).

[327] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.q.18 ).

[328] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.q.19 ).

[329] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.s.18 ).

[330] Also of special preference are compositions 14.1 to 14.3671, preferably 14.1 to 14.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only because they comprise, as active compound A, the pyridyl ether of the formula (I.s.19 ).

[331] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.w.18 ).

[332] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of the formula (I.w.19 ).

[333] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of formula (I. ac.18).

[334] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of formula (I. ac.19).

[335] Also of special preference 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 because they comprise, as active compound A, the pyridyl ether of formula (I. ae.18).

[336] Also of particular preference 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 because they comprise, as active compound A, the pyridyl ether of formula (I. ae.19).

[337] Also of special preference are compositions 21.1 to 21.3671, preferably 21.1 to 21.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only because they comprise, as active compound A, the pyridyl ether of formula (I. af.18).

[338] Also of particular preference are compositions 22.1 to 22.3671, preferably 22.1 to 22.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only because they comprise, as active compound A, the pyridyl ether of formula (I. af.19).

[339] Also of special preference are compositions 23.1 to 23.3671, preferably 23.1 to 23.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only because they comprise, as active compound A, the pyridyl ether of formula (I. ah.18).

[340] Also of special preference are compositions 24.1 to 23.3671, preferably 24.1 to 24.3653, which differ from the corresponding compositions 1.1 to 1.3671, preferably 1.1 to 1.3653, only because they comprise, as active compound A, the pyridyl ether of formula (I. ah.19).

[341] The present invention also relates to agrochemical compositions comprising at least one auxiliary and at least one pyridyl ether of formula (I) according to the present invention.

[342] An agrochemical composition comprises a pesticide-effective amount of a pyridyl ether of formula (I). The expression "effective amount" indicates an amount of the composition of compounds I, which is sufficient to control unwanted plants, especially for control of unwanted plants in crops (i.e. cultivated plants) and which does not result in substantial damage to the treated plants. This amount can vary over a wide range and depends on several factors, such as the plants to be controlled, the material or producing plants treated, the climatic conditions and the specific pyridyl ether of formula (I) used.

[343] The pyridyl ethers of formula (I), their N-oxides, salts or derivatives can be converted into customary types of agrochemical compositions, such as solutions, emulsions, suspensions, dry powders, powders, pastes, granules, presses, capsules and their mixtures. Examples of types of agrochemical compositions are suspensions (e.g. SC, OD and FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES and ME), capsules (e.g. CS and ZC ), pastes, tablets, dry or wettable powders (e.g. WP, SP, WS, DP and DS), pressed (e.g. BR, TB and DT), granules (e.g. WG, SG, GR, FG, GG and MG), insecticidal articles (e.g. LN) and also gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and other types of agrochemical compositions are defined in Catalog of Pesticide Formulation Types and International Coding System, Technical Monograph No. 2, 6th edition, May 2008, CropLife International.

[344] Agrochemical compositions are prepared in a known manner, as described by Mollet and Grubemann, Formulation Technology, Wiley VCH, Weinheim, 2001; or Knowles, New Developments in Crop Protection Product Formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[345] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, humectants, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants , compatibilizers, bactericides, antifreeze agents, antifoam agents, dyes, adhesives and binders.

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

[347] Suitable solid carriers or fillers are mineral earths, such as silicates, silica gel, talc, kaolin, lime, limestone, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate and magnesium oxide; polysaccharides, such as cellulose and starch; fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas; products of vegetable origin, such as cereal dough, tree bark dough, wood dough, nut shell dough and mixtures thereof.

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

[349] Suitable anionic surfactants are alkaline, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, oil and fatty acid sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalene sulfonates, dodecyl and tridecylbenzene sulfonates, naphthalene and alkylnaphthalene sulfonates, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of oils and fatty acids, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, carboxylated alcohol or alkylphenol ethoxylates.

[350] Suitable non-ionic 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 may 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, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, esters of glucose and sucrose or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinyl alcohols or vinyl acetate.

[351] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds with one or two hydrophobic groups or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are block polymers of type A-B or A-B-A comprising blocks of polyethylene oxide and polypropylene oxide or type A-B-C comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkaline salts of polyacid comb polymers or polyacrylic acid. Examples of polybases are polyvinylamines or polyethyleneamines.

[352] Suitable adjuvants are compounds that have negligible or no pesticidal activity in themselves and that improve the biological performance of the pyridyl ethers of formula (I) on the target. Examples are surfactants, mineral or vegetable oils and other auxiliaries. Additional examples are listed by Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

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

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

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

[356] Suitable defoaming agents are silicones, long-chain alcohols and fatty acid salts.

[357] Suitable dyes (for example, in red, blue or green) are pigments with low water solubility and water-soluble dyes. Examples are inorganic dyes (e.g. iron oxide, titanium oxide and iron hexacyanoferrate) and organic dyes (such as alizarin, azo and phthalocyanine dyes).

[358] Suitable binders or adhesives are polyvinylpyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, synthetic or biological waxes and cellulose ethers.

[359] Examples of types of agrochemical compositions and their preparation are: i. water-soluble concentrates (SL, LS):

[360] 10-60% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from herbicidal compounds B ( component B) and safety agents C (component C) according to the present invention and 5-15% by weight of wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or water-soluble solvent (e.g. alcohols) up to 100% by weight. The active substance is dissolved by diluting with water. ii. Dispersible concentrates (DC):

[361] 5-25% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from herbicidal compounds B ( component B) and safety agents C (component C) according to the present invention and 1-10% by weight of dispersant (e.g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) up to 100% in Weight. Dilution with water generates dispersion. iii. Emulsifiable concentrates (EC):

[362] 15-70% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from herbicidal compounds B ( component B) and safety agents C (component C) according to the present invention and 5-10% by weight of emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent ( e.g. aromatic hydrocarbon) up to 100% by weight. Dilution with water generates an emulsion. iv. Emulsions (EW, EO and ES):

[363] 5-40% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from herbicidal compounds B ( component B) and safety agents C (component C) according to the present invention and 1-10% by weight of emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40% by weight of water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water at 100% by weight using an emulsifying machine and transformed into a homogeneous emulsion. Dilution with water generates an emulsion. v. Suspensions (SC, OD and FS):

[364] In an agitated ball mill, 20-60% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention are fragmented with addition of 2-10% by weight of dispersants and wetting agents (e.g. sodium lignosulfonate and ethoxylate of alcohol), 0.1-2% by weight thickener (e.g. xanthan gum) and water up to 100% by weight to provide a fine active substance suspension. Dilution with water generates stable suspension of the active substance. For type FS composition, up to 40% by weight of binder (e.g. polyvinyl alcohol) is added. saw. Water-dispersible granules and water-soluble granules (WG and SG):

[365] 50-80% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from herbicidal compounds B ( component B) and safety agents C (component C) according to the present invention are finely ground with addition of dispersants and wetting agents (e.g., sodium lignosulfonate and alcohol ethoxylate) up to 100% by weight and prepared in the form of water-dispersible or water-soluble granules by means of technical devices (e.g. extrusion, spray tower and fluidized bed). Dilution with water generates a stable solution or dispersion of the active substance. viii. Water-dispersible powders and water-soluble powders (WP, SP, WS):

[366] 50-80% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from herbicidal compounds B ( component B) and safety agents C (component C) according to the present invention are ground in a rotor-stator mill with addition of 1-5% by weight of dispersants (e.g. sodium lignosulfonate), 1-3% by weight of wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) up to 100% by weight. Dilution with water generates a stable solution or dispersion of the active substance. viii. Gel (GW, GF):

[367] In an agitated ball mill, 5-25% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional selected compound from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention are fragmented with addition of 3-10% by weight of dispersants (e.g. sodium lignosulfonate, 1-5% by weight of thickener (e.g. carboxymethylcellulose) and water up to 100% by weight to provide a fine suspension of the active substance. Dilution with water generates stable suspension of the active substance iv.

[368] 5-20% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from herbicidal compounds B ( component B) and safety agents C (component C) according to the present invention are added to 5-30% by weight of organic solvent mixture (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of mixture of surfactants (e.g. alcohol ethoxylate and arylphenol ethoxylate) and water up to 100% by weight. This mixture is stirred for one hour to spontaneously produce a thermodynamically stable microemulsion. iv. Microcapsules (CS):

[369] An oil phase comprising 5-50% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention, 0-40% by weight of water-insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15% by weight weight of acrylic monomers (e.g., methyl methacrylate, methacrylic acid and di- or triacrylate) are dispersed in an aqueous solution of protective colloid (e.g., polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50% by weight of pyridyl ether of formula (I) according to the present invention, 0-40% by weight of water-insoluble organic solvent (e.g., aromatic hydrocarbon) and a Isocyanate monomer (e.g., diphenylmethene 4,4'-diisocyanate) is dispersed in an aqueous solution of protective colloid (e.g., polyvinyl alcohol). The addition of polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. Monomers represent 1-10% by weight. The weight percentage refers to the total CS composition. ix. Dustable powders (DP, DS):

[370] 1-10% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from herbicidal compounds B ( component B) and safety agents C (component C) according to the present invention are finely ground and mixed thoroughly with a solid carrier (e.g., finely divided kaolin) up to 100% by weight. x. Granules (GR, FG):

[371] 0.5-30% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from the herbicidal compounds B (component B) and safety agents C (component C) according to the present invention are finely ground and associated with a solid carrier (e.g. silicate) up to 100% by weight. Granulation is achieved through extrusion, spray drying or fluidized bed. xi. Ultra-low volume (UL) liquids:

[372] 1-50% by weight of pyridyl ether of formula (I) or herbicidal composition comprising at least one pyridyl ether of formula (I) (component A) and at least one additional compound selected from herbicidal compounds B ( component B) and safety agents C (component C) according to the present invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) up to 100% by weight.

[373] Agrochemical compositions of types (i) to (xi) may optionally comprise additional auxiliaries, such as 0.1-1% by weight of bactericides, 5-15% by weight of antifreeze agents, 0.1-1% by weight by weight of antifoaming agents and 0.1-1% by weight of dyes.

[374] Agrochemical compositions and/or herbicidal compositions generally comprise from 0.01 to 95%, preferably from 0.1 to 90% and, particularly, from 0.5 to 75% by weight of the pyridyl ethers of formula (I) . The pyridyl ethers of formula (I) are used in purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

[375] Seed treatment solutions (LS), suspoemulsions (SE), fluid concentrates (FS), dry treatment powders (DS), water-dispersible powders for spray treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are generally used for the treatment of plant propagation materials, particularly seeds. The agrochemical compositions in question provide, after dilution two to ten times, active substance concentrations of 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in ready-to-use preparations. Application can be carried out before or during sowing.

[376] Methods of applying pyridyl ethers of formula (I), their agrochemical compositions and/or herbicidal compositions to plant propagation material, especially seeds, include methods of application by covering, coating, pelletizing, dusting, soaking and in furrows of the propagation material. Preferably, pyridyl ethers of formula (I), their agrochemical compositions and/or herbicidal compositions, respectively, are applied to plant propagation material by a method that does not induce germination, such as by covering, pelletizing, coating and sprinkling the seeds.

[377] Various types of oils, humectants, adjuvants, fertilizers or additional micronutrients and pesticides (such as herbicides, insecticides, fungicides, growth regulators and safety agents) can be added to the pyridyl ethers of formula (I), to the agrochemical compositions and/or herbicidal compositions comprising them as premix or, if appropriate, not until immediately before use (tank mix). These agents can be mixed with the agrochemical compositions according to the present invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[378] The user applies the pyridyl ethers of formula (I) according to the present invention, the agrochemical compositions and/or herbicidal compositions comprising them normally from a pre-dosing device, knapsack sprayer, spray tank, spray plane or irrigation system. Typically, the agrochemical composition is compounded with water, buffer and/or additional auxiliaries to the desired application concentration and the ready-to-use spray liquid or agrochemical composition according to the present invention is thus obtained. Typically, 20 to 2000 liters, preferably 50 to 400 liters of ready-to-use spray liquid are applied per hectare of usable agricultural area.

[379] According to one embodiment, individual components of the agrochemical composition according to the present invention or partially pre-mixed components, such as components comprising pyridyl ethers of formula (I) and optionally active substances of groups B and/or C, may be mixed by the user in a spray tank and additional additives and auxiliaries may be added if appropriate.

[380] In a further embodiment, individual components of the agrochemical composition according to the present invention, such as parts of a kit or parts of a binary or ternary mixture, can be mixed by the user himself in a spray tank and can be auxiliary aggregates additional information, if appropriate.

[381] In a further embodiment, individual components of the agrochemical composition according to the present invention or partially pre-mixed components, such as components comprising pyridyl ethers of formula (I) and optionally active substances of groups B and/or C, may be applied together (such as after tank mixing) or consecutively.

[382] The pyridyl ethers of formula (I) are suitable as herbicides. They are intrinsically suitable, in the form of a suitably formulated composition (agrochemical composition) or herbicidal composition in combination with at least one additional compound selected from the active compounds such as herbicides B (component B) and safety agents C (component C).

[383] The pyridyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising the pyridyl ethers of formula (I) control vegetation over non-producing areas very efficiently, especially at high application rates. They act against broadleaf weeds and grasses in crops such as wheat, rice, corn, soybeans and cotton, without causing significant damage to the producing plants. This effect is mainly observed at low application rates.

[384] The pyridyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising them are applied to plants mainly by spraying the leaves. At this point, the application can be conducted using, for example, water as a vehicle through customary spraying methods, employing spray liquid amounts of about 100 to 1,000 l/ha (e.g. 300 to 400 l/ha). there is). The pyridyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising them can also be applied by means of the low volume or ultralow volume method, or in the form of microgranules.

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

[386] The pyridyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising them can be applied before or after emergence, before planting or together with seeds of producing plants. It is also possible to apply the pyridyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising them by applying seeds of producing plants, previously treated with the pyridyl ethers of formula (I) or the agrochemical compositions and /or the herbicidal compositions comprising them. If the active ingredients are less tolerated by certain producing plants, application methods can be used in which the herbicidal compositions are sprayed, with the aid of spray equipment, in such a way that, as far as possible, they do not come into contact with the leaves of sensitive producing plants, while the active ingredients reach the leaves of undesirable plants growing beneath them or the bare soil surface (post- directed, deposition).

[387] In a further embodiment, the pyridyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising them can be applied through seed treatment. Seed treatment essentially comprises all procedures familiar to those skilled in the art (seed covering, seed coating, seed dusting, seed soaking, seed film coating, multi-layer seed coating, seed encrustation, seed dipping, seeds and seed pelleting) based on the pyridyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions prepared with them. At this point, herbicidal compositions can be applied with or without dilution.

[388] The term “seed” comprises seeds of all types, such as corns, seeds, fruits, tubers, seedlings and similar forms. At present, the term seed preferably describes corns and seeds. The seed used may be the seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained through customary cultivation methods.

[389] When used in plant protection, the quantities of active substances applied, that is, the pyridyl ethers of formula (I), component B and, if appropriate, component C without formulation aids, are, depending on the type of desired effect, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 1.5 kg per ha and particularly from 0.1 to 1 kg per ha.

[390] In another embodiment of the present invention, the application rate of the pyridyl ethers of formula (I), component B and, if appropriate, component C is 0.001 to 3 kg/ha, preferably 0.005 to 2.5 kg/ha ha and, specifically, 0.01 to 2 kg/ha of active substance (s.a.).

[391] In another preferred embodiment of the present invention, the application rates of the pyridyl ethers of formula (I) according to the present invention (total amount of pyridyl ethers of formula (I)) are from 0.1 g/ha to 3,000 g/ha, preferably 1 g/ha to 1,000 g/ha, depending on target control, season, target plants and growth stage.

[392] In another preferred embodiment of the present invention, the application rates of the pyridyl ethers of formula (I) are in the range of 0.1 g/ha to 5,000 g/ha and, preferably, in the range of 0.5 g/ha to 2,500 g/ha or from 2.5 g/ha to 2,000 g/ha.

[393] In another preferred embodiment of the present invention, the application rate of the pyridyl ethers of formula (I) is 0.1 to 1,000 g/ha, preferably 0.5 to 750 g/ha and, more preferably, from 2.5 to 500 g/ha.

[394] The required application rates of B herbicidal compounds are generally in the range of 0.0005 kg/ha to 2.5 kg/ha, preferably in the range of 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/ha of s.a.

[395] The required application rates of C safety agents are generally in the range of 0.0005 kg/ha to 2.5 kg/ha, preferably in the range of 0.005 kg/ha to 2 kg/ha or 0. 01 kg/ha to 1.5 kg/ha of s.a.

[396] When treating plant propagation materials such as seeds, for example by means of dusting, coating or soaking seeds, amounts of active substance of 0.1 to 1,000 g, preferably 1 to 1,000 g, are generally required. more preferably 1 to 100 g and, more preferably, 5 to 100 g, per 100 kg of plant propagation material (preferably seeds).

[397] In another embodiment of the present invention, to treat seeds, the amounts of active substances applied, that is, the pyridyl ethers of formula (I), component B and, if appropriate, component C are generally employed in amounts of 0.001 to 10 kg per 100 kg of seeds.

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

[399] In the case of herbicidal compositions according to the present invention, it does not matter whether the pyridyl ethers of formula (I), component B and/or additional component C are formulated and applied together or separately. In the case of separate application, the order in which the application takes place is of less importance. It is only necessary that the pyridyl ethers of formula (I), component B and/or additional component C are applied within a period of time that allows simultaneous action of the active ingredients on the plants, preferably within a period of, at maximum, 14 days, particularly a maximum of 7 days.

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

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

[402] Especially preferred crops are cereal crops, corn, soybeans, rice, canola, cotton, potatoes, peanuts, or permanent crops.

[403] The pyridyl ethers of formula (I) according to the present invention or the agrochemical 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 has been modified by the use of recombinant DNA methods to include an inserted sequence of DNA that is not native to the genome of that plant species or to exhibit deletion of DNA that was native to the genome of that species, where the modification(s) cannot be easily obtained through breeding, mutagenesis or natural recombination alone. Often, a specific genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a process of propagation or natural cultivation from an ancestral plant whose genome was directly treated using a method of recombinant DNA. Typically, one or more genes have been integrated into the genetic material of genetically modified plants in order to enhance certain properties of the plant. These genetic modifications also include, but are not limited to, targeted post-translational modification of protein(s), oligos or polypeptides, for example, through the inclusion within them of amino acid mutation(s) that allow(s), m) or promote glycosylation or polymer additions such as prenylation, acetylation, farnesylation or attachment of PEG moieties.

[404] Plants that have been modified through breeding, mutagenesis or genetic engineering, for example, that have become tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; leach herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvyl 3-phosphate shikimate synthase (EPSP) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors, such as glufosinate; protoporphyrinogen IX oxidase inhibitors; lipid biosynthesis inhibitors, such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynyl herbicides (such as bromoxynil or ioxynil) as a result of conventional breeding methods or genetic engineering; Furthermore, plants have become resistant to various classes of herbicides through various genetic modifications, such as resistance to glyphosate and glufosinate or both, glyphosate and a herbicide from another class, such as ALS inhibitors, HPPD inhibitors, herbicides. of auxin or ACCase inhibitors. These herbicide resistance technologies are, for example, described 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 references mentioned there. Several cultivated plants have become tolerant to herbicides through mutagenesis and conventional breeding methods, such as summer canola Clearfield® (Canola, BASF SE, Germany), which is tolerant to imidazolinones such as imazamox, or sunflower ExpressSun® ( DuPont, United States), which is tolerant to sulfonyl ureas such as tribenuron. Genetic engineering methods have been used to make cultivated plants, such as soybeans, cotton, corn, beets and canola, tolerant to herbicides such as glyphosate, imidazolinones and glufosinate, some of which are in development or are commercially available under the brand names or RoundupReady® (glyphosate tolerant, Monsanto, United States), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany).

[405] Furthermore, plants are also covered which, using recombinant DNA methods, are capable of synthesizing one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, by example CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; plant insecticidal proteins (VIP), such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from bacteria-colonizing nematodes, such as Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins or other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins; plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome deactivating proteins (RIP), such as ricin, maize RIP, Abrin, lufin, saporin or bryodin; steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glucosyltransferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as sodium or calcium channel blockers; juvenile esterase hormone; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention, these insecticidal toxins or proteins should also be expressly understood to include pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains (see, for example, WO 02/015701). Additional examples of such toxins or genetically modified plants capable of synthesizing such toxins are described, for example, in EP-A 374,753, WO 93/007278, WO 95/34656, EP-A 427,529, EP-A 451,878, WO 03/18810 and WO 03/52073. Methods of producing such genetically modified plants are generally known to those skilled in the art and described, for example, in the publications mentioned above. These insecticidal proteins contained in genetically modified plants impose tolerance on plants producing these proteins to weedy pests from all taxonomic groups of arthropods, especially beetles (coleoptera), two-winged insects (diptera), moths (lepidoptera) and nematodes (Nematoda). Genetically modified plants capable of synthesizing one or more insecticidal proteins are, for example, described in the publications mentioned above and some of them are commercially available, such as YieldGard® (corn cultivars producing the Cry1Ab toxin), YieldGard® Plus (corn cultivars producing of the toxins Cry1Ab and Cry3Bb1), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin N-acetyltransferase (PAT)); NuCOTN® 33B (cotton cultivars producing Cry1Ac toxin), Bollgard® I (cotton cultivars producing Cry1Ac toxin), Bollgard® II (cotton cultivars producing Cry1Ac and Cry2Ab2 toxins); VIPCOT® (VIP toxin-producing cotton cultivars); NewLeaf® (potato cultivars that produce the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e.g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (corn cultivars producing Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, cf. WO 03/018810), MON 863 from Monsanto Europe S. A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S. A., Belgium (cotton cultivars producing a modified version of the Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1F toxin and PAT enzyme).

[406] In addition, plants are also covered that, using recombinant DNA methods, are capable of synthesizing one or more proteins to increase the resistance or tolerance of these plants to bacterial, viral or fungal pathogens. Examples of such proteins are so-called “pathogenesis-related proteins” (PR proteins; see, for example, EP-A 392,225), plant disease resistance genes (such as potato cultivars that express resistance genes that act against derived Phytophthora infestans from the Mexican wild potato, Solanum bulbocastanum) or T4 lysozyme (such as potato cultivars capable of synthesizing these proteins with greater resistance against bacteria such as Erwinia amylovora). Methods of producing such genetically modified plants are generally known to those skilled in the art and described, for example, in the publications mentioned above.

[407] In addition, plants are also covered that, using recombinant DNA methods, are capable of synthesizing one or more proteins to increase productivity (such as biomass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity, other environmental factors limiting growth or tolerance to pests and fungal, bacterial or viral pathogens of these plants.

[408] In addition, plants that contain, using recombinant DNA methods, modified amounts of ingredients or novel ingredients specifically to improve human or animal nutrition are also covered, such as oilseed crops that produce long-chain omega-3 fatty acids. health benefits or unsaturated omega-9 fatty acids (such as canola Nexera®, Dow Agro Sciences, Canada).

[409] In addition, plants are also covered which, using recombinant DNA methods, contain modified amounts of ingredients or novel ingredients specifically to increase the production of starting material, such as potatoes which produce greater amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).

[410] It was further concluded that the pyridyl ethers of formula (I) according to the present invention or the agrochemical compositions and/or herbicidal compositions comprising them are also suitable for defoliation and/or dissection of plant parts, for the which are suitable producing plants such as cotton, potatoes, canola, sunflower, soybeans or field beans, particularly cotton. In this particular, agrochemical compositions and/or herbicidal compositions for dissection and/or defoliation of plants, processes for preparing these agrochemical compositions and/or herbicidal compositions and methods of dissection and/or defoliation of plants using the pyridyl ethers of formula (I) were found. ).

[411] As desiccants, the pyridyl ethers of Formula (I) are particularly suitable for dissecting the aerial parts of producing plants such as potatoes, canola, sunflower and soybeans, but also cereals. This makes it possible to fully mechanically harvest these important producing plants.

[412] It is also of economic interest to facilitate harvesting, which is made possible by concentrating on a certain period of time the dehiscence or reduction of adherence to the tree, in citrus fruits, olives and other species and varieties of fruits in pomes, drupes and nuts. The same mechanism, i.e., promotion of the development of abscission tissue between fruit part or leaf part and shoot part of plants is also essential for controlled defoliation of useful plants, particularly cotton.

[413] Furthermore, reducing the time interval in which individual cotton plants mature leads to increased fiber quality after harvest.

[414] It was further concluded that the pyridyl ethers of formula (I) or the agrochemical compositions and/or herbicidal compositions comprising the pyridyl ethers of formula (I) also very efficiently control PPO-resistant herbs.

[415] Consequently, the present invention also provides a method of controlling the growth of PPO-resistant herbs, which comprises contacting these herbs, their parts, their propagation material or their habitat with pyridyl ethers of formula (I), wherein PPO-resistant herbs are herbs that are resistant to PPO-inhibiting herbicides, except pyridyl ethers of formula (I).

[416] The present invention specifically relates to a method of controlling PPO-resistant herbs in crops, which comprises applying pyridyl ethers of formula (I) to producing plants, in which said PPO herbicide-resistant herbs occur or may occur.

[417] As used herein, the expressions “PPO inhibitor”, “PPO inhibitor herbicide”, “herbicide that inhibits PPO”, “protoporphyrinogen IX oxidase inhibitor herbicide”, “herbicide that inhibits protoporphyrinogen IX oxidase”, “ protoporphyrinogene oxidase inhibitor herbicide” and “herbicide that inhibits protoporphyrinogene oxidase” are synonymous and designate a herbicide that inhibits the protoporphyrinogene oxidase enzyme in plants.

[418] As used herein, the expressions “PPO-inhibiting herbicide-resistant herb”, “PPO-inhibiting herbicide-resistant herb”, “PPO-inhibitor-resistant herb”, “PPO-resistant herb”, “PPO-resistant herb the herbicide that inhibits protoporphyrinogen IX oxidase”, “herbicide-resistant herb that inhibits protoporphyrinogen IX oxidase”, “herbicide-resistant herbicide that inhibits protoporphyrinogen oxidase” and “herbicide-resistant herb that inhibits protoporphyrinogene oxidase” are synonyms and designate a plant that, with respect to a treatment with an appropriate or above-appropriate rate of herbicide application that inhibits PPO, has inherited, developed, or acquired the ability to: [1] survive that treatment if it is lethal to wild-type weed (i.e., eradicate -The); or [2] exhibit significant plant growth or thrive after that treatment if it suppresses the growth of the wild-type herb.

[419] Effective weed control is defined as suppression of at least 70% of the weeds or their eradication from producing plants, or plant phytotoxicity of at least 70% of the weeds, as determined two weeks after treatment.

[420] PPO-resistant herbs are therefore herbs that are not controlled by the application of PPO inhibitors, except the pyridyl ethers of formula (I), while the corresponding sensitive biotype is controlled at that rate of use.

[421] “Uncontrolled” indicates at present that, on visual assessment, weed control (herbicidal effect) is < 70% weed suppression or eradication, as determined within two weeks after treatment; and “controlled” indicates that, on visual assessment, weed control is >90% weed suppression or eradication, as determined within two weeks of treatment.

[422] Preferably, PPO-resistant weeds are weeds that are not controlled (i.e., on visual assessment, weed control is < 70% weed suppression or eradication as determined within two weeks of treatment) by the application of herbicides. PPO inhibitors, except for the pyridyl ethers of formula (I).

[423] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks after treatment) by the application of PPO inhibitor herbicides selected from azafenidin.

[424] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks after treatment) by the application of PPO inhibitor herbicides selected from azafenidin, falesafen and lactofen.

[425] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks after treatment) by the application of PPO inhibitor herbicides selected from medosafen and lactofen.

[426] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks after treatment) by the application of PPO inhibitor herbicides selected from acifluorfen, azafenidin, carfentrazone, flumiclorac, flumioxazin, medosafen, lactofen, oxadiazon, oxyfluorfen, pyraflufen and sulfentrazone.

[427] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks after treatment) by the application of PPO inhibitor herbicides selected from acifluorfen, carfentrazone, flumiclorac, flumioxazin, medosafen, lactofen, oxadiazon, oxyfluorfen, pyraflufen and sulfentrazone.

[428] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by means of application rate of: - 200 g/ha or less; - preferably specific, 100 g/ha or less; - preferably special, 50 to 200 g/ha; and - more preferably, 50 to 100 g/ha; of PPO-inhibiting herbicides, other than pyridyl ethers of formula (I), while the corresponding sensitive biotype is controlled (i.e., on visual assessment, weed control is >90% weed suppression or eradication, as determined in two weeks after treatment), at that usage rate.

[429] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by means of application rate of: - 200 g/ha or less; preferably specifically, 100 g/ha or less; preferably, 50 to 200 g/ha; and more preferably, 50 to 100 g/ha; of PPO inhibitor herbicides selected from azafenidin, falesafen, and lactofen while the corresponding sensitive biotype is controlled (i.e., on visual assessment, weed control is >90% weed suppression or eradication as determined within two weeks after treatment), at that usage rate.

[430] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by means of application rate of: - 200 g/ha or less; - preferably specific, 100 g/ha or less; - preferably special, 50 to 200 g/ha; and - more preferably, 50 to 100 g/ha; of PPO inhibitor herbicides selected from falesafen and lactofen while the corresponding sensitive biotype is controlled (i.e., on visual assessment, weed control is >90% weed suppression or eradication as determined within two weeks of treatment), at that usage rate.

[431] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by means of application rate of: - 200 g/ha or less; preferably specifically, 100 g/ha or less; preferably, 50 to 200 g/ha; and more preferably, 50 to 100 g/ha; of PPO inhibitor herbicides selected from acifluorfen, azafenidin, carfentrazone, flumiclorac, flumioxazin, medosafen, lactofen, oxadiazon, oxyfluorfen, piraflufen and sulfentrazone, while the corresponding sensitive biotype is controlled (i.e., on visual assessment, control of the weeds is >90% weed suppression or eradication, as determined within two weeks of treatment), at that rate of use.

[432] Also preferably, PPO-resistant herbs are herbs that are not controlled (i.e., on visual assessment, herb control is < 70% weed suppression or eradication as determined within two weeks of treatment) by means of application rate of: - 200 g/ha or less; preferably specifically, 100 g/ha or less; preferably, 50 to 200 g/ha; and more preferably, 50 to 100 g/ha; of PPO inhibitor herbicides selected from acifluorfen, carfentrazone, flumiclorac, flumioxazin, falesafen, lactofen, oxadiazon, oxyfluorfen, pyraflufen and sulfentrazone, while the corresponding sensitive biotype is controlled (i.e., on visual assessment, weed control is > 90% weed suppression or eradication, as determined within two weeks of treatment), at that rate of use.

[433] PPO-resistant herbs are also preferably those classified as being “PPO-resistant” and therefore related 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).

[434] Of specific preference, PPO-resistant herbs are selected from the group consisting of Acalypha ssp, Amaranthus ssp, Ambrosia ssp, Avena ssp, Conyza ssp, Descurainia ssp, Euphorbia ssp and Senecio ssp; with special preference, Amaranthus ssp, Ambrosia ssp and Euphorbia ssp; and more preferably, Amaranthus ssp and Ambrosia ssp.

[435] Particularly preferred PPO-resistant herbs are also selected from the group consisting of: - Asian copperleaf (Acalypha australis), cockscomb (Amaranthus hybridus), Palmer amaranth (Amaranthus palmeri), pigweed (Amaranthus retroflexus ), tall/common pigweed (Amaranthus tuberculatus, Amaranthus rudis or Amaranthus tamariscinus), carpenterwort (Ambrosia artemisiifolia), wild oat (Avena fatua), avoadinha (Conyza ambigua), Canadian avoadinha (Conyza canadensis), sophia grass (Descurainia sophia ), wild peanut (Euphorbia heterophyla) and dead thistle (Senecio vernalis); with special preference, cockscomb (Amaranthus hybridus), Palmer amaranth (Amaranthus palmeri), pigweed (Amaranthus retroflexus), tall/common pigweed (Amaranthus tuberculatus or Amaranthus rudis), carpenter bean (Ambrosia artemisiifolia) and wild peanut (Euphorbia heterophyla); most preferably, tall/common pigweed (Amaranthus tuberculatus, Amaranthus rudis or Amaranthus tamariscinus) and carpenterwort (Ambrosia artemisiifolia).

[436] Most PPO-resistant herbs, particularly Amaranthus tuberculatus biotypes, are resistant due to deletion of codons on the nuclear-encoded PPX2L gene encoding the PPO enzyme that has dual targets, mitochondria and chloroplasts. This results in loss of the amino acid glycine at position 210 (see, for example, B. G. Young et al, Characterization of PPO-Inhibitor- Resistant Waterhemp (Amaranthus tuberculatus) Response to Soil-Applied PPO-Inhibiting Herbicides, Weed Science 2015, 63, 511 -521).

[437] The second type of mutation, particularly in a resistant biotype of Ambrosia artemisiifolia, was identified as a mutation that expressed the R98L alteration of the PPX2 enzyme (S. L. Rousonelos, R. M. Lee, M. S. Moreira, M. J. VanGessel and P. J. Tranel, Characterization of a Common Ragweed ( Ambrosia artemisiifolia) Population Resistant to ALS- and PPO-Inhibiting Herbicides, Weed Science 60, 2012, 335-344).

[438] Consequently, preferentially PPO-resistant herbs are herbs whose Protox enzyme is resistant to the application of PPO inhibitors due to a mutation expressed as ΔG210 or R98L change of said Protox enzyme or equivalents to PPX2L or PPX2, respectively, particularly expressed as change ΔG210 or R98L of the aforementioned Protox enzyme.

[439] The preparation of the phenyluracils of formula (I) is illustrated by examples; The object of the present invention, however, is not limited to the examples provided. A. Examples of preparations:

EXAMPLE 1

[440] 2-[2-[[3-Chloro-6-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-5-fluoro-2- pyridyl]oxy]phenoxy]ethyl acetate:

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

[442] To a solution of 0.5 g (2.98 mmol) of 2,3,6-trifluoro-5-chloropyridine (CAS 2879-42-7) in 7 ml of EtOH, 0.23 g was added (2.98 mmol) of 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 of step 1.

[443] 1H NMR (CDCl3, ppm): 7.33 (dd, J=9.00 Hz, J=6.63 Hz, 1 H); 6.05 (br.s, 1 H); 3.84 (br.s, 2 H).

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

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

[446] To a solution of 0.58 g (3.23 mmol) of compound 1 from step 1 in 13 ml of EtOH was added 0.29 g (3.23 mmol) of pyruvic acid in drops. 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 of step 2.

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

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

[449] To a solution of 3.4 g (13.6 mmol) of compound 1 from step 2 in 45 ml of toluene, 1.38 g (13.6 mmol) of triethylamine was added, followed by dropwise addition of 3.75 g (13.6 mmol) of diphenyl phosphoryl azide at room temperature. The mixture was kept at reflux for three hours, cooled to room temperature and stirred for another 18 hours. The mixture was washed with saturated aqueous Na2CO3. The aqueous layer was extracted with ethyl acetate. The combined organic layer was 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 generate 1.9 g (7.72 mmol, 57%) of the desired compound 1 from step 3.

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

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

[452] To a solution of 28.0 g (113 mmol) of compound 1 from step 3 in 455 ml of acetonitrile, 17.3 g (125 mmol) of potassium carbonate was added, followed by 27.7 g (136 mmol) of ethyl bromodifluoroacetate at room temperature. The mixture was refluxed for six hours, cooled to room temperature and stirred at room temperature for an additional 18 hours. The solvent was removed under reduced pressure, ethyl acetate was added and the mixture was washed with water. The organic layer was 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 generate 3.24 g (10.95 mmol, 10%) of the desired compound 1 from step 4.

[453] 1H NMR (CDCl3, ppm): 7.82 (dd, J=7.46 Hz, J=6.77 Hz, 1 H); 7.04 (t, J=57.94 Hz, 1 H); 2.50 (s, 3 H).

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

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

[456] To a solution of 2.8 g (9.47 mmol) of compound 1 from step 4 in 38 ml of tetrahydrofuran, 3.09 g (9.47 mmol) of cesium carbonate was added, followed by 1.86 g (9.47 mmol) of ethyl 2-(2-hydroxyphenoxy)acetate (CAS 99186-63-7). The mixture was kept at reflux 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 adding 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 layer was washed with saturated aqueous NaCl, 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 3.20 g (6.77 mmol, 71%) of the desired compound 1.

[457] 1H NMR (CDCl3, ppm): 7.75 (d, J=7.77 Hz, 1 H); 7.23 (dd, J=7.91 Hz, J=1.63 Hz, 1 H); 7.19 (ddd, J=8.17 Hz, J=7.57 Hz, J=1.67 Hz, 1 H); 7.04 (dt, J=7.77 Hz, J=7.77 Hz, J=1.46 Hz, 1 H); 6.95 (t, J=58.13 Hz, 1 H); 6.93 (dd, J=8.18 Hz, J=1.44 Hz, 1 H); 4.57 (s, 2H); 4.15 (q, J=7.14 Hz, 2 H); 2.37 (s, 3H); 1.21 (t, J=7.14 Hz, 3 H).

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

EXAMPLE 2

[459] 2-[2-[[3-Carbamothioyl-5-fluoro-6-[4-methyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]-2- pyridyl]oxy]phenoxy]ethyl acetate.

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

[461] To a solution of 2.5 g (16.0 mmol) of 4-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-one (CAS 51856-10-1) in 40 ml of dimethyl sulfoxide, 2.4 g (16.0 mmol) of 2,5,6-trifluoropyridine-3-carbonitrile (CAS 870065-73-9) and 2.2 g (16.0 mmol) were added. of potassium carbonate. The mixture was stirred for 16 hours at 20 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was 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 generate 3.1 g (9.6 mmol, 60%) of the desired compound 2 from step 1.

[462] 1H NMR (CDCl3, ppm): 7.96-8.08 (m, 1H); 3.43-3.60 (m, 3 H).

[463] Step 2: 5-fluoro-2-(2-methoxyphenoxy)-6-[4-methyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]pyridine-3 -carbonitrile.

[464] To a solution of 1.1 g (3.6 mmol) of compound 2 from step 1 in 20 ml of dimethyl sulfoxide, 0.45 g (3.6 mmol) of 2-methoxyphenol (CAS) was added 90-05-1) and 0.99 g (7.2 mmol) of potassium carbonate. The mixture was stirred for 16 hours at 50 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure to provide the desired compound 2 from step 2 (2.5 g) which was used without further purification in the next step.

[465] Step 3: 5-fluoro-2-(2-hydroxyphenoxy)-6-[4-methyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]pyridine-3 -carbonitrile.

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

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

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

[469] 1H NMR (CDCl3, ppm): 7.95 (d, J=7.78 Hz, 1H); 7.21-7.26 (m, 2H); 7.04-7.10 (m, 1H); 6.94 (dd, J=8.16, 1.25 Hz, 1H); 4.59 (s, 2H); 4,094.18 (m, 2H); 3.39 (s, 3H).

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

EXAMPLE 3

[471] 2-[2-[[3-Carbamothioyl-5-fluoro-6-[4-methyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]-2- pyridyl]oxy]phenoxy]ethyl acetate.

[472] Hydrogen sulfide was bubbled through a solution of 0.2 g (0.4 mmol) of compound 2 from step 4 (compound 2) in 10 ml of pyridine and 2 ml of triethylamine at 15 ° C. The mixture was then stirred for 2 hours at 15 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was 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.

[473] 1H NMR (CDCl3, ppm): 9.41 (br s, 1H); 8.73 (d, J=9.54 Hz, 1H); 8.17 (br s, 1H); 7.52 (dd, J=8.03, 1.51 Hz, 1H); 7.19-7.26 (m, 1H); 7.06-7.14 (m, 1H); 6.93 (d, J=8.16 Hz, 1H); 4.59 (s, 2H); 4.22 (q, J=7.15 Hz, 2H); 3.41 (s, 3H); 1.27 (t, J=7.15 Hz, 3H).

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

EXAMPLE 4

[475] 2-[2-[[3,5-Dichloro-6-(3-oxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a] pyridin-2-yl)-2-pyridyl]oxy]phenoxy]ethyl acetate:

[476] Step 1: 2-(3,5,6-trichloro-2-pyridyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin -3-ona.

[477] 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, 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 for 17 hours at 20 °C and then for 17 hours at 100 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was 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 generate 3.5 g (9.78 mmol, 16%) of the desired compound 4 from step 1.

[478] 1H NMR (CDCl3, ppm): 7.95-8.07 (m, 1H); 7.27 (d, J=2.51 Hz, 1H); 3.64-3.74 (m, 2H); 2.76-2.84 (m, 2H), 1.90-2.09 (m, 6H).

[479] Step 2: 2-[3,5-dichloro-6-(2-methoxyphenoxy)-2-pyridyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4 ,3-a]pyridin-3-one.

[480] To a solution of 2.5 g (7.9 mmol) of compound 4 from step 1 in 25 ml of DMF, 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 for 17 hours at 100 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was 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 generate 3.2 g (7.9 mmol, 99%) of the desired compound 4 from step 2.

[481] 1H NMR (CDCl3, ppm): 7.90 (s, 1H); 7.15-7.21 (m, 2H); 6.85-6.99 (m, 3H); 3.76 (s, 3H); 3.61 (t, J=6.06 Hz, 2H); 2.68 (t, J=6.39 Hz, 2H); 1.79-1.97 (m, 5H).

[482] Step 3: 2-[3,5-dichloro-6-(2-hydroxyphenoxy)-2-pyridyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[4 ,3-a]pyridin-3-one.

[483] 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° W. The mixture was stirred for 17 hours at 20 °C. The mixture was poured into ice water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure to provide the desired product 4 from step 3 (2.5 g) which was used without further purification in the next step.

[484] 1H NMR (CDCl3, ppm): 7.92 (s, 1H); 7.22 (d, J=7.50 Hz, 1H); 7.10-7.17 (m, 2H); 6.95-7.01 (m, 1H); 6.78-6.89 (m, 3H); 3.66 (t, J=6.06 Hz, 2H); 2.73 (t, J=6.39 Hz, 2H); 1.83-2.01 (m, 4H).

[485] Step 4: 2-[2-[[3,5-dichloro-6-(3-oxo-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3 -a]pyridin-2-yl)-2-pyridyl]oxy]phenoxy]ethyl acetate.

[486] To a solution of 1.0 g (2.5 mmol) of compound 4 from step 3 in 10 ml of acetonitrile, 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 for 17 hours at 20 °C. 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.

[487] 1H NMR (CDCl3, ppm): 7.92 (s, 1H); 7.24 (dd, J=7.91, 1.51 Hz, 1H); 7.17 (td, J=7.87, 1.57 Hz, 1H); 7.01-7.06 (m, 1H); 6.92-6.96 (m, 1H); 4.59 (s, 2H); 4.18 (q, J=7.15 Hz, 2H); 3.61 (t, J=6.02 Hz, 2H); 2.68 (t, J=6.40 Hz, 2H); 1.89-1.97 (m, 2H); 1.82-1.89 (m, 2H); 1.23 (t, J=7.15 Hz, 3H).

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

EXAMPLE 5

[489] 2-[2-[[6-(5-tert-Butyl-2-oxo-1,3,4-oxadiazol-3-yl)-3,5-dichloro-2-pyridyl]oxy]phenoxy] ethyl acetate.

[490] Step 1: 5-tert-butyl-3-[3,5-dichloro-6-(2-methoxyphenoxy)-2-pyridyl]-1,3,4-oxadiazol-2-one.

[491] To a solution of 4.5 g (14.0 mmol) of 5-tert-butyl-3-(3,5-dichloro-6-fluoro-2-pyridyl)-1,3,4-oxadiazole- 2-one (CAS 68617-97-0) in 50 ml of DMF, 1.7 g (14.0 mmol) of 2-methoxyphenol (CAS 90-05-1) and 5.8 g (42.0 mmol) were added. 0 mmol) of potassium carbonate. The mixture was stirred for 17 hours at 80 °C. The mixture was diluted with water and extracted with methyl tert-butyl ether. The combined organic layer was 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 generate 2.4 g (5.88 mmol, 42%) of the desired compound 5 from step 1.

[492] 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).

[493] Step 2: 5-tert-butyl-3-[3,5-dichloro-6-(2-hydroxyphenoxy)-2-pyridyl]-1,3,4-oxadiazol-2-one.

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

[495] 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).

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

[497] To a solution of 2.0 g (5.0 mmol) of compound 5 from step 2 in 20 ml of acetonitrile, 1.69 g (10.0 mmol) of ethyl 2-bromoacetate (CAS) was added 105-36-2) and 2.79 g (20.0 mmol) of potassium carbonate. The mixture was stirred for 17 hours at 20 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was 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 0.3 g (0.6 mmol, 12%) of the desired compound 5.

[498] 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).

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

EXAMPLE 6

[500] 2-[2-[[3-chloro-6-[4-chloro-5-(difluoromethoxy)-1-methylpyrazol-3-yl]-5-fluoro-2-pyridyl]oxy]phenoxy]acetate ethyl.

[501] Step 1: 4-chloro-5-(difluoromethoxy)-3-iodo-1-methylpyrazole.

[502] To a solution of 5.2 g (20.56 mmol) of iodine in 25 ml of acetonitrile, 2.12 g (20.56 mmol) of tert-butyl nitrile was added at 0 ° C under an atmosphere of argon. The mixture was stirred for one hour at 0°C and 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 for 2 hours at 20 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with aqueous Na2S2O3, 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 generate 3.2 g (15.6 mmol, 76%) of the desired compound 6 from step 1.

[503] Step 2: tributyl-[4-chloro-5-(difluoromethoxy)-1-methylpyrazol-3-yl]tin.

[504] To a solution of 2.2 g (7.15 mmol) of compound 6 from step 1 in 40 ml of tetrahydrofuran, 4.3 ml (8.6 mmol, 2M in THF) of hydrogen chloride were added. iso-propyl magnesium at -10 °C under an argon atmosphere. The mixture was stirred for 15 minutes at -10°C and then 2.8 g of tributyltin chloride (CAS 1461-22-9) was slowly added at -10°C. The mixture was stirred for 1.5 hours at 20 °C. The mixture was cooled with saturated aqueous NH4Cl solution and extracted with ethyl acetate. The combined organic layer was 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 generate 2.5 g (5.4 mmol, 75%) of the desired compound 6 from step 2.

[505] 1H NMR (CDCl3, ppm): 6.82 (d, J=1.10 Hz, 1H); 6.63 (d, J=1.32 Hz,1H); 6.45 (d, J=1.32 Hz, 1H); 3.77 (s, 3H); 1.48-1.65 (m, 6H); 1,101.39 (m, 17H); 0.80-0.96 (m, 16H).

[506] Step 3: 2-bromo-5-chloro-3-fluoro-6-(2-methoxyphenoxy)pyridine.

[507] To a solution of 7.7 g (107.8 mmol) of sodium azide in 120 ml of dimethyl sulfoxide at 0 °C, 18.0 g (118.6 mmol) of 3-chloro- 2,5,6-trifluoropyridine (CAS 2879-42-7). The mixture was stirred for 3 hours at 20 °C. A solution of 14.0 g (113.0 mmol) of 2-methoxyphenol (CAS 90-05-1) was then 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 layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to provide the desired product 6 from step 3 which was used without further purification in the next step.

[508] Step 4: 5-chloro-3-fluoro-6-(2-methoxyphenoxy)pyridin-2-amine.

[509] To a suspension of 18.0 g (61.1 mmol) of compound 6 from step 3 and 35.0 g (537.0 mmol) of zinc in 400 ml of tetrahydrofuran, 350 ml were added dropwise of a semi-saturated aqueous NH4Cl solution at 0 °C. The mixture was stirred for 3 hours at 20 °C, filtered and the filter pad 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 generate 16.0 g (59.5 mmol, 97%) of the desired product 6 from step 4.

[510] Step 5: 2-bromo-5-chloro-3-fluoro-6-(2-methoxyphenoxy)pyridine.

[511] To a solution of 7.0 g (26.1 mmol) of compound 6 from step 4 in 70 ml of acetonitrile, 5.8 g (26.1 mmol) of copper (II) bromide was added and 3.0 g (28.7 mmol) tert-butyl nitrite drops at -15 °C. The mixture was stirred for 2 hours at 20 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was 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 generate 8.4 g (11.0 mmol, 42%) of the desired compound 6 from step 5.

[512] 1H NMR (CDCl3, ppm): 7.57 (d, J=6.39 Hz, 1H); 7.21-7.26 (m, 1H); 7.12-7.17 (m, 1H); 6.97-7.04 (m, 2H); 3.76 (s, 3H).

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

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

[515] 1H NMR (CDCl3, ppm): 7.62 (d, J=6.17 Hz, 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=7.06 Hz, 1H); 2.05 (s, 2H); 1.27 (t, J=7.06 Hz, 2H).

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

[517] To a solution of 2.0 g (6.2 mmol) of compound 6 from step 6 in 20 ml of acetonitrile, 1.7 g (12.2 mmol) of potassium carbonate and 2.1 g (12.6 mmol) of ethyl 2-bromoacetate (CAS 105-36-2) in drops. The mixture was stirred for 17 hours at 20 °C. The mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was 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 generate 2.0 g (4.96 mmol, 80%) of the desired compound 6 from step 7.

[518] 1H NMR (MeOD, ppm): 7.91 (d, J=6.78 Hz, 1H); 7.14-7.27 (m, 2H); 7.04-7.09 (m, 2H); 4.58 (s, 2H); 4.15 (q, J=7.07 Hz, 2H); 1.22 (t, J=7.09 Hz, 3H).

[519] Step 8: 2-[2-[[3-chloro-6-[4-chloro-5-(difluoromethoxy)-1-methylpyrazol-3-yl]-5-fluoro-2-pyridyl]oxy]phenoxy ]ethyl acetate.

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

[521] 1H NMR (CDCl3, ppm): 7.67 (d, J=8.78 Hz, 1H); 7.24 (br d, J=7.91 Hz, 1H); 7.17 (br t, J=7.59 Hz, 1H); 7.01-7.08 (m, 1H); 6.93 (br d, J=8.16 Hz, 1H); 6.78 (s, 1H); 6.60 (s, 1H); 6.42 (s, 1H); 4.53 (s, 2H); 4.16 (q, J=6.99 Hz, 2H); 3.79 (s, 3H); 1.21 (t, J=7.09 Hz, 3H).

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

EXAMPLE 7

[523] 2-[[3-[[3-Chloro-6-(3,5-dimethyl-2,4,6-trioxo-1,3,5-triazinan-1-yl)-5-fluoro-2 -pyridyl]oxy]-2-pyridyl]oxy]ethyl acetate:

[524] Step 1: Ethyl 2-[[3-[(6-azido-3-chloro-5-fluoro-2-pyridyl)oxy]-2-pyridyl]oxy]acetate.

[525] To a solution of 1.8 g (10.78 mmol) of 3-chloro-2,5,6-trifluoropyridine (CAS 2879-42-7) in 20 ml of dimethyl sulfoxide at 23 ° C, were 0.77 g (11.8 mmol) of sodium azide were added. The mixture was stirred for 3 hours at 23 °C. A suspension of 2.2 g (11.3 mmol) of ethyl 2-[(3-hydroxy-2-pyridyl)oxy]acetate (CAS: 353292-81-6) and 7.0 g (21.5 mmol ) of cesium carbonate in 10 ml of dimethyl sulfoxide was added portionwise 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 layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to provide the desired product from step 1 which was used without further purification in the next step.

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

[527] Step 2: Ethyl 2-[[3-[(6-amino-3-chloro-5-fluoro-2-pyridyl)oxy]-2-pyridyl]oxy]acetate.

[528] To a suspension of 4.8 g (13.0 mmol) of compound 7 from step 1 and 4.3 g (66.0 mmol) of zinc in 100 ml of tetrahydrofuran, 50 ml were added dropwise. of a semi-saturated aqueous NH4Cl solution at 0 °C. The mixture was stirred at 23 °C for 5 hours, filtered and the filter pad was washed with ethyl acetate. 200 ml of water were 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 generate 2.7 g (8.0 mmol, 61%) of the desired product 7 from step 2.

[529] 1H NMR (CDCl3, ppm): 7.9 (dd, J=4.89 Hz, J=1.51 Hz, 1H); 7.4 (d, J=7.39 Hz, 1H); 7.3 (d, J=9.06 Hz, 1H); 6.9 (dd, J=7.65 Hz, J=4.89 Hz, 1H); 4.9 (s, 2H); 4.5 (s, 2H); 4.2 (q, J=7.15 Hz, 2H); 1.25 (t, J=7.15 Hz, 3H).

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

[531] Step 3: 2-[[3-[[3-chloro-6-(3,5-dimethyl-2,4,6-trioxo-1,3,5-triazinan-1-yl)-5- ethyl fluoro-2-pyridyl]oxy]-2-pyridyl]oxy]acetate.

[532] To a solution of 1.0 g (3.1 mmol) of compound 7 from step 2 in 10 ml of ethyl acetate, 1.5 g (9.2 mmol) of carbonyldiimidazole and 0 .9 g (9.6 mmol) of triethylamine. The mixture was stirred for two hours at 65°C before adding 0.27 g (3.1 mmol) of N,N-dimethyl urea. The mixture was stirred for another 17 hours at 65 °C. The mixture was diluted with ice water, the pH was adjusted to 7 with 6N HCl and extracted with ethyl acetate. The combined organic layer was 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.

[533] 1H NMR (CDCl3, ppm): 7.97 (dd, J=5.02, 1.51 Hz, 1H); 7.77 (d, J=7.15 Hz, 1H); 7.49 (dd, J=7.65, 1.63 Hz, 1H); 6.96 (dd, J=7.72, 4.96 Hz, 1H); 4.78 (s, 2H); 4.19 (q, J=7.15 Hz, 2H), 3.34 (s, 6H); 1.25 (t, J=7.09 Hz, 3H).

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

EXAMPLE 8

[535] 2-[[3-[[3-Chloro-5-fluoro-6-[5-methyl-6-oxo-4-(trifluoromethyl)pyridazin-1-yl]-2-pyridyl]oxy]-2 -pyridyl]oxy]ethyl acetate:

[536] 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) was added -6) and 4.0 g (12.3 mmol) of cesium carbonate. The mixture was stirred for 17 hours at 20 °C. 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.

[537] 1H NMR (CDCl3, ppm): 7.97 (dd, J=4.96, 1.65 Hz, 1H); 7.91 (s, 1H); 7.78 (d, J=7.50 Hz, 1H); 7.51 (dd, J=7.72, 1.54 Hz, 1H); 6.96 (dd, J=7.72, 4.85 Hz, 1H); 4.81 (s, 2H); 4.17 (q, J=7.06 Hz, 2H); 2.35-2.38 (m, 3H); 1.23 (t, J=7.06 Hz, 3H).

[538] [M+H] = 503.0; Rt = 1.284 min.

[539] The compounds listed below in Tables 1 to 9 can be prepared in a similar way to the example mentioned above. where R3 and R4 are H, R5 is OR6, R6 is C2H5, n is 1, Q, W and X are O, Y is Y20, A1 is O, R21 is CF2H, R22 is CH3, Z is Z-1 and Ra, Rb, Rc and Rd are HTABLE 1 where R3 and R4 are H, R5 is OR6, R6 is C2H5, n is 1, Q, W and X are O, Y is Y20, A1 is O, R21 is CF2H, R22 is CH3, Z is Z-7 and Ra, Rb and Rc are HTABLE 2 m where R1 is F, R3 and R4 are H, R5 is OR6, R6 is C2H5, n is 1, Q, W and X are O, Y is Y20, R21 is CH3, R22 is CF3, Z is Z-1 and Ra, Rb, Rc and Rd are HTABLE 3 where R3 and R4 are H, R5 is OR9, R6 is C2H5, n is 1, Q, W and X are O, Y is Y2, R23 is CF2H, R24 is CH3, R28 is Cl, Z is Z-7 and Ra, Rb and Rc are H TABLE 4 where R3 and R4 are H, R5 is OR6, R6 is C2H5, n is 1, Q, W and X are O, Y is Y67, A1 and A2 are O, A3 is S, R35 and R36 are CH3, Z is Z-7 and Ra, Rb and Rc are H TABLE 5 where R3 and R4 are H, R5 is OR6, R6 is C2H5, n is 1, Q, W and X are O, Y is Y55, A1 is O, R17 is CF3, R18 is CH3, R28 is H, Z is Z-1 and Ra, Rb, Rc and Rd are HTABLE 6 where R3 and R4 are H, R5 is OR6, R6 is C2H5, n is 1, Q, W and X are O, Y is Y66, A1 is O, R12 is CF3, R13 is H, R35 is CH3, Z is Z-1 and Ra, Rb, Rc and Rd are H TABLE 7 where R3 and R4 are H, R5 is OR6, R6 is C2H5, n is 1, Q, W and X are O, Y is Y65, A1 is O, R12 is H, R13 is CF3, R35 is CH3, Z is Z-1 and Ra, Rb, Rc and Rd are H TABLE 8 where R3 and R4 are H, R5 is OR6, R6 is C2H5, n is 1, Q, W and X are O, Y is Y65, A1 is O, R12 is H, R13 is CF3, R35 is CH3, Z is Z-7 and Ra, Rb and Rc are H TABLE 9

EXAMPLE 26

[540] Ethyl 2-[2-[[3-chloro-5-fluoro-6-(5-isopropylidene-2,4-dioxo-oxazolidin-3-yl)-2-pyridyl]oxy]phenoxy]acetate.

[541] Step 1: Ethyl 2-[2-[(6-amino-3-chloro-5-fluoro-2-pyridyl)oxy]phenoxy]acetate.

[542] To a solution of 40 g (0.24 mol) of 3-chloro-2,5,6-trifluoropyridine (CAS 2879-42-7) in 400 ml of dimethyl sulfoxide at 23 ° C, 17 g (0.26 mol) of sodium azide. The mixture was stirred for 16 hours at 23 °C. A suspension of 49 g (0.25 mol) of ethyl 2-(2-hydroxyphenoxy)acetate (CAS: 99186-63-7) and 155 g (0.48 mol) of cesium carbonate in 100 ml of dimethyl sulfoxide. The resulting mixture was stirred at 23 °C for 15 hours, diluted with water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure to provide the desired product from step 1 which was used without further purification in the next step.

[543] [M+H] = 367.0; Rt = 1.276 min.

[544] Step 2: ethyl 2-[2-[(6-amino-3-chloro-5-fluoro-2-pyridyl)oxy]phenoxy]acetate.

[545] To a suspension of 34 g (93.0 mmol) of compound 26 from step 1 and 15.1 g (232.0 mmol) of zinc in 190 ml of tetrahydrofuran, 150 ml of a semi-saturated aqueous NH4Cl solution at 0 °C. The mixture was stirred at 23 °C for 15 hours, filtered and the filter pad was washed with ethyl acetate. 200 ml of water were 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 give the desired product 26 from step 2, which was used without additional purification in the next step.

[546] 1H NMR (CDCl3, ppm): 7.34 (d, J = 9.0 Hz, 1H), 7.18-7.09 (m, 2H), 7.06-6.99 (m, 1H), 6.95 (dd, J=8.1, 1.5 Hz, 1H), 4.57 (s, 2H), 4.20 (q, J=7.1 Hz, 2H), 3, 97 (br, 2H), 1.25 (t, J=7.1 Hz, 3H).

[547] [M+H] = 341.1; Rt = 1.123 min.

[548] Step 3: 2-[2-[[3-chloro-5-fluoro-6-(5-isopropylidene-2,4-dioxo-oxazolidin-3-yl)-2-pyridyl]oxy]phenoxy]acetate of ethyl.

[549] To a solution of 250 mg (0.73 mmol) of compound 26 from step 2 in 8 ml of acetonitrile, 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 one hour before adding 106 mg (0.73 mmol) of ethyl 2-hydroxy-3-methylbut-3-enoate. The mixture was stirred for another 17 hours at 80 °C. 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.

[550] 1H NMR (CDCl3, ppm): 7.77 (d, J = 7.3 Hz, 1H), 7.23-7.15 (m, 2H), 7.03 (td, J = 7, 8, 1.5 Hz, 1H), 6.88 (dd, J = 8.1, 1.5 Hz, 1H), 4.53 (s, 2H), 4.16 (q, J = 7.1 Hz, 2H), 2.21 (s, 3H), 1.98 (s, 3H), 1.22 (t, J = 7.1 Hz, 3H).

[551] [M+H] = 464.9; Rt = 1.288.

EXAMPLE 27

[552] 2-[2-[[3-Chloro-6-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-5-fluoro-2-pyridyl]oxy] phenoxy]ethyl acetate.

[553] Step 1: 2-[5-chloro-3-fluoro-6-(2-methoxyphenoxy)-2-pyridyl]-4,5,6,7-tetrahydroisoindole-1,3-dione.

[554] To a solution of 1.0 g (3.7 mmol) of compound 6 from step 4 in 30 ml of toluene, 850 mg (5.6 mmol) of 3,4,5,6-anhydride was added. tetrahydrophthalic acid (CAS 2426-02-0) and 1.0 g (5.6 mmol) of p-toluenesulfonic acid monohydrate (CAS 6192-52-5). The mixture was stirred for 16 hours at 100 °C. 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 generate 715 mg (1.7 mmol, 48%) of the desired product from step 1.

[555] [M+H] = 403.0; Rt = 1.284.

[556] Step 2: 2-[5-chloro-3-fluoro-6-(2-hydroxyphenoxy)-2-pyridyl]-4,5,6,7-tetrahydroisoindole-1,3-dione.

[557] To a solution of 660 mg (1.6 mmol) of compound 27 from step 1 in 12 ml of dichloromethane, 820 mg (3.3 mmol) of boron tribromide was added dropwise at -60 ° C. The mixture was stirred for 15 hours at 20 °C. The mixture was poured into ice water and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure to provide the desired product from step 2 (630 mg) which was used without further purification in the next step.

[558] [M+H] = 389.0; Rt = 1.165.

[559] Step 3: 2-[2-[[3-chloro-6-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-5-fluoro-2-pyridyl ]oxy]phenoxy]ethyl acetate.

[560] To a solution of 630 mg (1.6 mmol) of compound 27 from step 2 in 10 ml of dimethyl formamide, 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 for 15 hours at 23 °C. The mixture was diluted with water and extracted with methyl tert-butyl ether. The combined organic layer was 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.

[561] [M+H] = 475.0; Rt = 1.292.

[562] 1H NMR (CDCl3, ppm): 7.71 (d, J = 7.4 Hz, 1H), 7.21 (dd, J = 7.8, 1.6 Hz, 1H), 7.16 (td, J = 7.8, 1.6 Hz, 1H), 7.02 (td, J = 7.7, 1.4 Hz, 1H), 6.90 (dd, J = 8.1, 1 .4 Hz, 1H), 4.57 (s, 2H), 4.17 (q, J = 7.2 Hz, 2H), 2.38-2.29 (m, 4H), 1.76 (p , J = 3.0 Hz, 4H), 1.22 (t, J = 7.2 Hz, 3H). 8. Usage examples:

[563] The herbicidal activity of the pyridylethers of formula (I) was demonstrated through the following greenhouse experiments.

[564] The cultivation containers used were plastic flower pots containing silty sand with about 3.0% humus as substrate. Seeds from test plants were grown separately for each species.

[565] For pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after cultivation through fine distribution nozzles. The containers were gently irrigated to promote germination and growth and then covered with transparent plastic hoods until the plants took root. This coating caused uniform germination of the test plants unless it was prevented by the active ingredients. For post-emergence treatment, test plants were first grown to a height of 3 to 15 cm, depending on the plant's habits, and only then treated with the active ingredients that had been suspended or emulsified in water. For this purpose, test plants were directly cultivated and grown in the same containers or were first grown separately as seedlings and transplanted into the test containers a few days before treatment. Depending on the species, plants were maintained at 10-25°C or 20-35°C, respectively.

[566] The trial period extended for two to four weeks. During this period, the plants received care and their reaction to individual treatments was evaluated. The assessment was conducted using a scale from 0 to 100. 100 indicates no emergence of plants or complete destruction of at least the aerial parts and 0 indicates no damage or normal course of growth. Good herbicidal activity is provided at values of at least 70 and very good herbicidal activity is provided at values of at least 85.

[567] The plants used in the greenhouse experiments belonged to the following species:

[568] At an application rate of 16 g/ha, compounds (examples) 1, 8, 10, 12, 13, 15, 17, 19, 20, 22, 24 and 25 applied through the post-emergence method demonstrated very good herbicidal activity against AMARE, CHEAL, ECHCG and SETVI.

[569] At an application rate of 16 g/ha, compound (example) 2 applied via the post-emergence method exhibited very good herbicidal activity against AMARE, ECHCG and SETVI.

[570] At an application rate of 16 g/ha, compound (example) 3, 4 and 7 applied via the post-emergence method exhibited good herbicidal activity against AMARE.

[571] At an application rate of 16 g/ha, compound (example) 5 applied via the post-emergence method exhibited very good herbicidal activity against AMARE and CHEAL.

[572] At an application rate of 16 g/ha, compounds (examples) 6 and 21 applied via the post-emergence method exhibited very good herbicidal activity against AMARE, CHEAL, SETVI and POLCO.

[573] At an application rate of 16 g/ha, compound (example) 9 applied via the post-emergence method exhibited very good herbicidal activity against CHEAL, ECHCG and SETVI.

[574] At an application rate of 16 g/ha, compound (example) 11 applied via the post-emergence method exhibited very good herbicidal activity against CHEAL and good herbicidal activity against POLCO.

[575] At an application rate of 16 g/ha, compound (example) 14 applied via the post-emergence method exhibited very good herbicidal activity against SETVI.

[576] At an application rate of 16 g/ha, compound (example) 16 applied via the post-emergence method exhibited very good herbicidal activity against AMARE, CHEAL and POLCO.

[577] At an application rate of 16 g/ha, compound (example) 18 applied via the post-emergence method exhibited very good herbicidal activity against AMARE and good herbicidal activity against SETVI.

[578] At an application rate of 16 g/ha, compound (example) 26 applied via the post-emergence method exhibited very good herbicidal activity against AMARE, CHEAL, POLCO and SETVI.

[579] At an application rate of 16 g/ha, compound (example) 27 applied via the post-emergence method exhibited very good herbicidal activity against AMARE, CHEAL, ECHG, POLCO and SETVI. TABLE 10

[580] Comparison of the herbicidal activity of Example 28 according to the present invention: (= compound of formula (I), where R1 = F; R2 = Cl; R3, R4 = H; R5 = OR6 where R6 = CH3; n = 1; Q, W, X = O; Y = Y55 in that R17 = CF3, R18 = CH3, R28 = H, A1 = O and Z = Z-3 where Ra, Rb, Rd and Re = H) and compound no. A2-11 known from JP 2001/270867 :

[581] Post-emergence control within 7 days after treatment (greenhouse):

[582] The data clearly demonstrate the superior herbicidal activity of the compounds of formula (I) according to the present invention compared to compounds according to the prior art.

[583] Replacement of the central phenyl ring with a pyridine ring generates much better herbicidal activity, as achieved by the compound known through JP 2001/270867.

Claims (8)

1. PYRIDIL ETHERS, characterized by being of formula (I): where the variables have the following meanings: - R1 is H or halogen; - R2 is H or halogen; - R3 is H; - R4 is H; - R5 is OR6, where - R6 is hydrogen or C1-C6 alkyl; - n is 1; - Q is O; - W is O; - X is O; - Y is a heterocycle selected from the group consisting of Y31, Y38, Y55, Y65, Y67 or Y68: where - A1, A2 and A3 are oxygen or sulfur; - R12, R13, R17 and R18 are hydrogen, C1-C6 alkyl or C1-C6 haloalkyl; or - R12 and R13, together with the atoms to which they are bonded, form a six-membered cycle, which is saturated or partially unsaturated; - R26 and R27 are C1-C6 alkyl; - R28 is hydrogen; - R35 and R36 are C1-C6 alkyl; - Z is Z-1 or Z-7; where - symbolizes the connection point from Z to X; - * symbolizes the connection point from Z to Q; and Ra, Rb, Rc and Rd are hydrogen, including their agriculturally acceptable salts or amides, esters and thioesters, provided that the compounds of formula (I) contain a carboxyl group. 2. PYRIDIL ETHERS, according to claim 1, characterized in that R1 is H or F and R2 is F, Cl or CN. 3. PYRIDYL ETHERS, according to any one of claims 1 to 2, characterized in that Y is selected from Y67. 4. PROCESS FOR PREPARING PYRIDYL ETHERS of formula (I), as defined in claim 1, characterized by pyridines of formula (II): wherein R1, R2 and Y are as defined in claim 1; and - L1 is halogen, C1-C6 alkyl sulfonate or aryl sulfonate; be reacted with compounds of formula (iii): wherein R3, R4, R5, n, Q, W, X and Z are as defined in claim 1; in the presence of a base. 5. HERBICIDAL COMPOSITION, characterized in that it comprises a herbicidally active amount of at least one pyridyl ether of formula (I), as defined in claim 1, and at least one inert solid and/or liquid carrier and, if appropriate, at least one surfactant substance. 6. PROCESS FOR PREPARING ACTIVE COMPOSITIONS such as herbicides, characterized in that it comprises mixing a herbicide-active amount of at least one pyridyl ether of formula (I), as defined in claim 1, and at least one solid and/or liquid carrier inert and, if desired, at least one surface-active substance. 7. METHOD FOR CONTROLING UNWANTED VEGETATION, characterized in that it comprises maintaining an active quantity as herbicide of at least one pyridyl ether of formula (I), as defined in claim 1, in action on plants, their environment or on seeds. 8. USE OF PYRIDIL ETHERS of formula (I), as defined in claim 1, characterized by being as herbicides.