Herbicidal 2-phenoxybutanoylamides

Abstract

The present invention relates to 2-phenoxybutanoylamide compounds of formula (I) (I) or agriculturally acceptable salts or stereoisomers thereof wherein the variables X, R1, R2 , R3, R4, R5 and R6 are defined as given in the description and claims. The invention also relates to compositions comprising the compounds I and to the use of the compounds I or the corresponding compositions for controlling undesired vegetation. Furthermore, the invention relates to methods for controlling undesired vegetation by using the compounds I or the corresponding compositions.

Description

[0001] Herbicidal 2-phenoxybutanoylamides

[0002] The present invention relates to 2-phenoxybutanoylamides of formula (I) defined below as well as to compositions comprising the same. The invention also relates to the use of said 2-phe- noxybutanoylamides or the corresponding compositions for controlling undesired vegetation. Furthermore, the invention relates to methods for controlling undesired vegetation by using said 2-phenoxybutanoylamides or the corresponding compositions.

[0003] Control of undesired vegetation (weeds) is a critical and pressing concern in agricultural practice, impacting crop productivity and overall agricultural sustainability. Weeds compete with crops for essential resources such as water, nutrients, and sunlight. Their rapid growth and aggressive nature can significantly reduce crop yields if not adequately controlled. Over time, weeds can develop resistance to herbicides, making them less susceptible to chemical control methods. This can render certain herbicides ineffective and limit the options available for weed management.

[0004] Addressing these challenges requires innovative solutions and continuous research and development efforts to enhance weed control strategies while minimizing their impact on the environment and crop productivity. New herbicides that have high activity and selectivity along with a substantial lack of toxicity for humans and animals belong to such innovative solutions.

[0005] US 4,119,433 describes 3-halo-5-(lower alkoxy) phenoxy alkyl amides and their use as herbicides.

[0006] The prior art compounds, however, often suffer from insufficient herbicidal activity, in particular at low aplication rates, and / or unsatisfactory selectivity, resulting in a low compatibility with crop plants.

[0007] Accordingly, it is an object of the present invention to provide further herbicidally active compounds having a strong herbicidal activity, in particular even at low application rates, a sufficiently low toxicity for humans and animals and / or a high compatibility with crop plants. The compounds should also show a broad activity spectrum against a large number of different unwanted plants. Further, the compounds should provide weed control over an adequately long period, thus allowing flexible application.

[0008] These and further objectives are achieved by the compounds of formula (I) defined below including their agriculturally acceptable salts or stereoisomers.

[0009] Accordingly, the present invention relates to a compound of the general formula (I) wherein

[0010] X is O, NH, NCH3, NOCH3, NOH, or S;

[0011] R1is selected from H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, C2-Ce-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, phenyl unsubstituted or substituted by 1 , 2 or 3 halogen atoms, which may be the same or different, or phenylmethylene wherein the phenyl moiety may be substituted by 1 , 2 or 3 halogen atoms, which may be the same or different;

[0012] R2is H or halogen;

[0013] R3is selected from halogen, CN, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, or Ci-Ce-haloal- koxy;

[0014] R4is selected from H, halogen, CN, Ci-Ce-alkyl, Ci-Ce-alkoxy, or Ci-Ce-haloalkoxy;

[0015] R5is selected from halogen, CN, Ci-Ce-alkyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, or Ci-Ce-haloalkoxy;

[0016] R6is H or halogen; or agriculturally acceptable salts or stereoisomers thereof.

[0017] The articles “a”, “an” and "the" each refer to one or more, unless otherwise indicated.

[0018] Depending on the kind of substituents, the compounds of formula (I) may have one or more centers of chirality, in which case they may be present as mixtures of enantiomers or diastereomers but also in the form of the pure enantiomers or pure diastereomers. The invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compounds of formula I or their mixtures. Suitable compounds of formula I also include all possible geometrical stereoisomers (cis / trans isomers) as a specific form of diastereomers and mixtures thereof. Cis / trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond, amide group or a cyclic, non-aromatic moiety. The term "stereoisomer(s)" encompasses both optical isomers, such as enantiomers or diastereomers existing due to more than one stereogenic center in the molecule, as well as geometrical isomers (cis / trans isomers).

[0019] At the carbon atom to which the phenoxy group is attached, the compounds of formula I and their agriculturally acceptable salts have a chiral center. A preferred embodiment of the invention relates to the racemates of the compounds of formula I and their agriculturally acceptable salts. Another preferred embodiment of the invention relates to the pure enantiomers of the compounds of formula I and their agriculturally acceptable salts having a 2-R- or 2-S-configura- tion at said chiral center, i.e. the compounds of formulae I-2R and I-2S as shown below. Racemates of the compounds of formula I and the enantiomer having the 2-R-configuration, i.e. the compound of formula I-2R, at the chiral center including their agriculturally acceptable salts are particularly preferred.

[0020] Chiral center

[0021] *chiral center

[0022] In the compounds of formula I and agriculturally acceptable salts thereof, the double bond to which the moiety C(O)XR1is attached can have a cis- or trans-configuration. Preference is given to those compounds of formula I and agriculturally acceptable salts thereof in which said double bond has a trans-configuration.

[0023] If the compounds of formula (I) have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.

[0024] Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyeth-1-oxy)eth-1- ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-hy- droxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium, and finally the salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[0025] Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-al- kanoic acids, preferably formate, acetate, propionate and butyrate.

[0026] Compounds of formula (I) having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally acceptable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-Ce-alkyla- mides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-C -alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as Ci-Cw-alkylthio esters. Preferred mono- and di-Ci-Ce-alkylamides are the methyl and the dimethylamides. Preferred arylamides are, for example, the anilides and the 2-chloroanilides. Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or

[0027] 3-butoxypropyl ester. An example of a straight-chain or branched Ci-Cio-al kylthio ester is the ethylthio ester.

[0028] The organic moieties mentioned in the definitions of the variables (substituents) R1, R2, R3, R4, noR5, and R6are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cn-Cmindicates in each case the possible number of carbon atoms in the group.

[0029] The term "halogen" denotes fluorine, bromine, chlorine or iodine.

[0030] The term "alkyl" denotes a straight-chain or branched saturated hydrocarbon group having usually 1 to 6 carbon atoms (Ci-Ce-alkyl), more frequently 1 to 4 carbon atoms (Ci-C4-alkyl), especially 1 to 3 carbon atoms (Ci-Cs-alkyl) or 1 or 2 carbon atoms (Ci-C2-alkyl). Examples of Ci-Ce- alkyl are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl (= sec-butyl), isobutyl and tert-butyl, n-pentyl, 1 -methyl butyl, 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-di- methylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1 , 1 ,2-trimethylpropyl, 1,2,2-trime- thylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl and the like.

[0031] The term "haloalkyl" denotes an alkyl group as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms. Examples of Ci-Ce-haloalkyl are fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluo- roethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 1 -chloroethyl, 2-chloroethyl, 2, 2, -dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,

[0032] 1-bromoethyl, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropro- pyl, heptafluoropropyl, 1 , 1 , 1 -trifluoroprop-2-yl, 3-chloropropyl, and the like.

[0033] The term "alkenyl" denotes an unsaturated straight-chain or branched hydrocarbon group having usually 2 to 6 carbon atoms (C2-Ce-alkenyl), more frequently 2 to 4 carbon atoms (C2-C4- alkenyl) or 2 to 3 carbon atoms (C2-C3-alkenyl), and a double bond in any position. Examples of C2-Ce-alkenyl are ethenyl, 1-propenyl, 2-propenyl, 1 -methylethenyl, 1-butenyl, 2-butenyl, 3-bu- tenyl, 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-

[0034] 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-di- methyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl,

[0035] 4-hexenyl, 5-hexenyl, 1 -methyl- 1 -pentenyl, 2-methyl-1 -pentenyl, 3-methyl-1-pentenyl, 4-me- thyl-1 -pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pen- tenyl, 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-

[0036] 2-butenyl, 1,1-dimethyl-3-butenyl, 1 ,2-dimethyl-1-butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,2-dimethyl-

[0037] 3-butenyl, 1,3-dimethyl-1-butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dime- thyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dime- thyl-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-me- thyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like.

[0038] The term "haloalkenyl" denotes an alkenyl group as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms, for example chlorovinyl, chloroallyl and the like. The term "alkynyl" denotes an unsaturated straight-chain or branched hydrocarbon groups having usually 2 to 6 carbon atoms (C2-Ce-alkynyl), more frequently 2 to 4 carbon atoms (C2-C4-al- kynyl) or 2 to 3 carbon atoms (C2-C3-alkynyl) and a triple bond in any position. Examples of C2-Ce-alkynyl are ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2- propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1 ,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl- 4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1 ,1-dimethyl-2-butynyl, 1 ,1-dimethyl-3-butynyl, 1 ,2- dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3- butynyl, 2-ethyl-3-butynyl, 1 -ethyl- 1-methyl-2-propynyl and the like.

[0039] The term "haloalkynyl" denotes an alkynyl group as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms.

[0040] The term "alkoxy" (O-alkyl) denotes an alkyl group as defined above, which is bound to the remainder of the molecule via an oxygen atom. Examples of Ci-Ce-alkoxy are methoxy, ethoxy, n- propoxy, 1 -methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy), 1 ,1 -dimethylethoxy (tert-butoxy), pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methyl pentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1-dimethylbut- oxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dime- thylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1-ethyl- 1 -methylpropoxy or 1-ethyl-2-methylpropoxy and the like.

[0041] The term "haloalkoxy" (O-haloalkyl) denotes an alkoxy group as defined above, wherein the hydrogen atoms are partially or fully replaced by halogen atoms. Examples of Ci-Ce-haloalkoxy are OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2, 2, 2-tri chloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2- bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2CI)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, nonafluorobutoxy, 5-fluoropentoxy, 5-chloro- pentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy and the like.

[0042] The term "alkoxy-alkyl" (alkyl-O-alkyl) refers to an alkyl group, as defined above, where one hydrogen atom is replaced by an alkoxy group, as defined above. For example, the term "C1-C4- alkoxy-Ci-C4-alkyl" refers to an alkyl group having 1 to 4 carbon atoms, as defined above, wherein one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, 1 -methoxyethyl, 1 -ethoxy- ethyl, 1-propoxyethyl, 1-isopropoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-iso- propoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 2-meth- oxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 3-methoxypropyl, 3-ethoxypro- pyl, 3-propoxypropyl, 3-isopropoxypropyl, 2-butoxyethyl (butotyl), 2-butoxypropyl, 3-butoxypro- pyl and the like.

[0043] The term "alkylthio" (S-alkyl or alkylsulfanyl) denotes an alkyl group as defined above, which is bound to the remainder of the molecule via a sulfur atom. Examples of Ci-C4-alkylthio are methylthio, ethylthio, n-propylthio, 1 -methylethylthio (isopropylthio), butylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio), 1 ,1 -dimethylethylthio (tert-butylthio) and the like.

[0044] The term "alkylthio-alkyl" (alkyl-S-alkyl or alkylsulfanyl-alkyl) refers to an alkyl group, as defined above, wherein one hydrogen atom is replaced by an alkylthio group, as defined above. For example, the term "Ci-C4-alkylthio-Ci-C4-alkyl" refers to an alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkylthio group, as defined above. Examples are methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n- propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, n-butylthiomethyl, n- butylthioethyl, n-butylthio-n-butyl and the like.

[0045] The term “phenylmethylene” denotes a phenyl ring attached via a methylene group (C6H5-CH2-) to the remainder of the molecule.

[0046] The preferred embodiments of the invention mentioned herein below have to be understood as being preferred either independently from each other or in combination with one another.

[0047] According to a preferred embodiment of the invention preference is also given to those compounds of formula (I), wherein the variables, either independently of one another or in combination with one another, have the following meanings:

[0048] Preferably, X is O, NH, NCH3, NOCH3, or NOH. More preferably, X is O or NOCH3. According to one embodiment, X is O. According to another embodiment X is NOCH3.

[0049] Preferably, R1is selected from H, Ci-Ce-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, or Ci-C4-alkylthio-Ci-C4-alkyl. More preferably, R1is selected from H, Ci-Ce-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or Ci-C4-alkylthio-Ci-C4-alkyl. Even more preferably, R1is selected from Ci-Ce-alkyl, C2-C4-alkenyl, or C2-C4-alkynyl.

[0050] In another preferred embodiment, R1is selected from H, methyl, ethyl, n-propyl, isopropyl, n- butyl, n-pentyl, 2-propenyl, prop-2-ynyl, 2,2-difluoroethyl, 2-methoxyethyl, or 2-ethylthioethyl, more preferably from H, methyl, ethyl, isopropyl, n-butyl, n-pentyl, 2-propenyl, prop-2-ynyl, or 2- ethylthioethyl and even more preferably from methyl, ethyl, 2-propenyl, or prop-2-ynyl.

[0051] Preferably, R2is selected from H, fluoro, chloro, or bromo, more preferably from H, fluoro, or chloro, and even more preferably from H or fluoro. Most preferably, R2is H. Preferably, R3is selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, or C1-C4- haloalkoxy, more preferably from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, or Ci-C4-haloalkoxy and even more preferably from halogen or Ci-C4-alkyl.

[0052] In another preferred embodiment, R3is selected from fluoro, chloro, bromo, methyl, difluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably from fluoro, chloro, bromo, methyl, difluoromethyl, or difluoromethoxy, and even more preferably fluoro, chloro, bromo, or methyl.

[0053] Preferably, R4is selected from H, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy, more preferably from H, halogen, Ci-C4-alkyl, or Ci-C4-alkoxy, and even more preferably from H, halogen or Ci-C4-alkyl.

[0054] In another preferred embodiment, R4is selected from H, fluoro, chloro, bromo, methyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably from H, fluoro, chloro, bromo, methyl, or methoxy, and even more preferably from H, fluoro, chloro, bromo, or methyl.

[0055] Preferably, R5is selected from halogen, CN, Ci-C4-alkyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C1-C4- alkoxy, or Ci-C4-haloalkoxy, more preferably from halogen, CN, Ci-C4-alkyl, C2-C4-alkynyl, C1- C4-haloalkyl, or Ci-C4-haloalkoxy, and even more preferably from halogen or Ci-C4-alkyl.

[0056] In another preferred embodiment, R5is selected from fluoro, chloro, bromo, CN, methyl, isopropyl, prop-1-ynyl, difluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably from fluoro, chloro, bromo, CN, methyl, isopropyl, prop-1-ynyl, difluoromethyl, difluoromethoxy, or trifluoromethoxy, and even more preferably from fluoro, chloro, bromo, or methyl.

[0057] Preferably, R6is selected from H, fluoro, chloro, or bromo, more preferably from H, fluoro, or chloro, and even more preferably from H or fluoro. Most preferably, R6is H.

[0058] In an especially preferred embodiment, R2and R6are both H.

[0059] Preference is also given to compounds of the formula I wherein

[0060] X is O, NH, NCH3, NOCH3, or NOH;

[0061] R1is selected from H, Ci-Ce-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, or Ci-C4-al- kylthio-Ci-C4-alkyl;

[0062] R2is H;

[0063] R3is selected from halogen or Ci-C4-alkyl;

[0064] R4is selected from H, halogen, Ci-C4-alkyl, or Ci-C4-alkoxy;

[0065] R5is selected from halogen, CN, Ci-C4-alkyl, C2-C4-alkynyl, Ci-C4-haloalkyl, or Ci-C4-haloal- koxy;

[0066] R6is H; or agriculturally acceptable salts or stereoisomers thereof.

[0067] Special preference is given to compounds of the formula I wherein X is O, NH, NCH3, NOCH3, or NOH; R1is selected from H, methyl, ethyl, isopropyl, n-butyl, n-pentyl, 2-propenyl, prop-2-ynyl, 2,2-difluoroethyl, or 2-ethylthioethyl;

[0068] R2is H;

[0069] R3is selected from fluoro, chloro, bromo or methyl;

[0070] R4is selected from H, fluoro, chloro, bromo, methyl, or methoxy;

[0071] R5is selected from fluoro, chloro, bromo, CN, methyl, isopropyl, prop-1-ynyl, difluoromethyl, difluoromethoxy, or trifluoromethoxy;

[0072] R6is H; or agriculturally acceptable salts or stereoisomers thereof.

[0073] Particular preference is given to compounds of the formula I wherein

[0074] X is O;

[0075] R1is selected from H, Ci-Ce-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or Ci-C4-alkylthio-Ci-C4-alkyl;

[0076] R2is H;

[0077] R3is selected from halogen or Ci-C4-alkyl;

[0078] R4is selected from H, halogen, Ci-C4-alkyl, or Ci-C4-alkoxy;

[0079] R5is selected from halogen, CN, Ci-C4-alkyl, C2-C4-alkynyl, Ci-C4-haloalkyl, or Ci-C4-haloal- koxy;

[0080] R6is H; or agriculturally acceptable salts or stereoisomers thereof.

[0081] Very particular preference is given to compounds of the formula I wherein

[0082] X is O;

[0083] R1is selected from H, methyl, ethyl, isopropyl, n-butyl, n-pentyl, 2-propenyl, prop-2-ynyl, or 2- ethylthioethyl;

[0084] R2is H;

[0085] R3is selected from fluoro, chloro, bromo or methyl;

[0086] R4is selected from H, fluoro, chloro, bromo, methyl, or methoxy;

[0087] R5is selected from fluoro, chloro, bromo, CN, methyl, isopropyl, prop-1-ynyl, difluoromethyl, difluoromethoxy, or trifluoromethoxy;

[0088] R6is H; or agriculturally acceptable salts or stereoisomers thereof.

[0089] In yet another preferred embodiment of the compounds of the formula I, R2and R6are both H.

[0090] These compounds correspond to formula I. a in which the variables have the meanings defined at the outset and preferably those mentioned above.

[0091] In yet another preferred embodiment of the compounds of the formula I, X is O and R2and R6are both H. These compounds correspond to formula l.b in which the variables have the meanings defined at the outset and preferably those mentioned above.

[0092] In yet another preferred embodiment of the compounds of the formula I, X is NOCH3 and R2and R6are both H. These compounds correspond to formula l.c in which the variables have the meanings defined at the outset and preferably those mentioned above.

[0093] Special preference is given to the compounds of the formulae l.a.1 to I. a.960 of Table A, where the definitions of the variables X, R1, R3, R4and R5are of particular importance for the compounds according to the invention not only in combination with one another but in each case also on their own:

[0094] Table A

[0095] Compounds of the formula I which correspond to the formula I. a as shown above

[0096] Preferred compounds of the formula I according to the invention are selected from the group consisting of the compounds 1-1 to I-82 as listed below (see also Table I in the Section “Synthesis examples”): - Methyl-(E)-4-[2-(3,5-dichlorophenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-1

[0097] - (E)-4-[2-(3,5-dichlorophenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-2 - methyl (E)-4-methyl-4-[2-(3, 4, 5-trichlorophenoxy)butanoylamino]pent-2-enoate of formula 1-3

[0098]

[0099] - (E)-4-methyl-4-[2-(3,4,5-trichlorophenoxy)butanoylamino]pent-2-enoic acid of formula 1-4 - methyl (E)-4-[2-(4-chloro-3,5-dimethyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-5

[0100] - methyl (E)-4-[2-(3-bromo-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-6

[0101]

[0102] - (E)-4-[2-(3-bromo-5-chloro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula I-

[0103] 7 - (E)-4-[2-(3-chloro-4,5-difluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula

[0104] 1-8

[0105] - (E)-4-[2-(3-chloro-5-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-9 - methyl (E)-4-[2-(3-chloro-5-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-10

[0106] - methyl (E)-4-[2-(3-bromo-5-chloro-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of for- mula l-11

[0107] - methyl (E)-4-[2-(3-chloro-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-12 - methyl (E)-4-[2-(3,5-dimethylphenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-13

[0108] - methyl (E)-4-[2-(3-fluoro-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-14 - methyl (E)-4-[2-(3-cyano-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-15

[0109] - (E)-4-[2-(3-bromo-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula I-

[0110] 16

[0111] - (E)-4-[2-(3-cyano-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula I-

[0112] - (E)-4-[2-(3,5-dimethylphenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-18

[0113] - methyl (E)-4-[2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-19

[0114] - (E)-4-[2-(4-chloro-3,5-dimethyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula I-20

[0115] - (E)-4-[2-(3-fluoro-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula I-

[0116] - methyl (E)-4-[2-(3,5-dichloro-4-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-22

[0117] - (E)-4-[2-(3-chloro-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula I-

[0118] 23 - (E)-4-[2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-24

[0119] - (E)-4-[2-(3,5-dichloro-4-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula

[0120] - (E)-4-[2-(4-chloro-3,5-difluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-26

[0121] - (E)-4-[2-(3-bromo-4,5-difluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-27

[0122]

[0123] - methyl (E)-4-[2-(3-bromo-4,5-difluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-28

[0124] - methyl (E)-4-[2-(4-chloro-3,5-difluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-29 - methyl (E)-4-[2-(3-chloro-5-cyano-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of for- mula 1-30

[0125] - (E)-4-[2-(3-chloro-5-cyano-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula I- 31

[0126] - (E)-4-[[(2S)-2-(3-bromo-5-chloro-phenoxy)butanoyl]amino]-4-methyl-pent-2-enoic acid of formula I-32

[0127] - (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoic acid of formula I-

[0128] 33

[0129] - methyl rac-(E)-4-methyl-4-[[rac-(2S)-2-(3-bromo-5-chloro-phenoxy)butanoyl]amino]pent-2- enoate of formula 1-34 - methyl rac-(E)-4-methyl-4-[[rac-(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]pent-2-enoate of formula 1-35

[0130] - (E)-4-methyl-4-[[(2S)-2-(3,4,5-trichlorophenoxy)butanoyl]amino]pent-2-enoic acid of formula 1-36

[0131] - (E)-4-[[(2S)-2-(3,5-dichloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2-enoic acid of formula 1-37 - methyl (E)-4-[[(2S)-2-(3,5-dichloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-38

[0132] - methyl (E)-4-methyl-4-[[(2S)-2-(3,4,5-trichlorophenoxy)butanoyl]amino]pent-2-enoate of formula 1-39

[0133]

[0134] - 2-ethylthioethyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-40 - butyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula

[0135] 1-41

[0136] - pentyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula I-42

[0137] - prop-2-ynyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-43 - isopropyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-44

[0138] - ethyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula

[0139]

[0140] - methyl (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-46 - methyl rac-(E)-4-methyl-4-[[rac-(2R)-2-(4-chloro-3,5-dimethyl-phenoxy)butanoyl]amino]pent-

[0141] 2-enoate of formula 1-47

[0142] - methyl rac-(E)-4-methyl-4-[[rac-(2R)-2-(3,5-dichloro-4-methyl-phenoxy)butanoyl]amino]pent- 2-enoate of formula 1-48

[0143]

[0144] - methyl (E)-4-[[(2R)-2-(3-fluoro-4,5-dimethyl-phenoxy)butanoyl]amino]-4-methyl-pent-2-eno- ate of formula 1-49 - methyl (E)-4-[[(2R)-2-(4-chloro-3-isopropyl-5-methyl-phenoxy)butanoyl]amino]-4-methyl-pent-

[0145] 2-enoate of formula 1-50

[0146] - methyl (E)-4-[[(2R)-2-[3-(difluoromethoxy)-5-fluoro-phenoxy]butanoyl]amino]-4-methyl-pent- 2-enoate of formula 1-51

[0147] - methyl (E)-4-[[(2R)-2-(3,5-dichloro-4-methoxy-phenoxy)butanoyl]amino]-4-methyl-pent-2-en- - methyl (E)-4-[[(2R)-2-(3-chloro-4-fluoro-5-methyl-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula I-53

[0148] - methyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula I-54

[0149] - methyl (E)-4-[[(2R)-2-[3-chloro-5-(difluoromethoxy)phenoxy]butanoyl]amino]-4-methyl-pent-2- enoate of formula 1-55

[0150] - methyl (E)-4-[[(2R)-2-(3-chloro-5-isopropyl-phenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-56

[0151] - methyl (E)-4-[[(2R)-2-(4-fluoro-3,5-dimethyl-phenoxy)butanoyl]amino]-4-methyl-pent-2-eno- ate of formula 1-57

[0152] - methyl (E)-4-[[(2R)-2-(3,5-dichloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-58 - methyl (E)-4-[[(2R)-2-(3-bromo-4,5-dichloro-phenoxy)butanoyl]amino]-4-methyl-pent-2-eno- ate of formula 1-59

[0153] - methyl (E)-4-[[(2R)-2-(3,5-dimethylphenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-60

[0154] - methyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-phenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-61 - methyl (E)-4-[[(2R)-2-(3,5-dibromophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of for- mula I-62

[0155] - methyl (E)-4-[[(2R)-2-[3-chloro-5-(trifluoromethoxy)phenoxy]butanoyl]amino]-4-methyl-pent-2- enoate of formula I-63 - methyl (E)-4-[[(2R)-2-(3,5-dibromo-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula I-64

[0156] - methyl (E)-4-[[(2R)-2-[3,4-dichloro-5-(trifluoromethoxy)phenoxy]butanoyl]amino]-4-methyl- pent-2-enoate of formula 1-65

[0157] - methyl (E)-4-methyl-4-[[(2R)-2-(3,4,5-tribromophenoxy)butanoyl]amino]pent-2-enoate of formula 1-66

[0158] - methyl (E)-4-[2-(3-chloro-5-prop-1-ynyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula I-67 - methyl rac-(E)-4-methyl-4-[[rac-(2R)-2-(4-bromo-3,5-dichloro-phenoxy)butanoyl]amino]pent- 2-enoate of formula 1-68

[0159] - (E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2-enoic acid of formula 1-69

[0160] - methyl rac-(E)-4-methyl-4-[[rac-(2R)-2-[3-chloro-5-(difluoromethyl)phenoxy]buta- noyl]amino]pent-2-enoate of formula 1-70 - methyl rac-(E)-4-methyl-4-[[rac-(2R)-2-(3,4-dichloro-5-methyl-phenoxy)butanoyl]amino]pent-

[0161] 2-enoate of formula 1-71

[0162] - rac-(E)-4-methyl-4-[[rac-(2R)-2-(3,5-dichloro-4-fluoro-phenoxy)butanoyl]amino]pent-2-enoic acid of formula I-72

[0163] - ethyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2-en- oate of formula 1-73 - isopropyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-

[0164] 2-enoate of formula 1-74

[0165] - prop-2-ynyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl- pent-2-enoate of formula 1-75

[0166] - allyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2-eno- ate of formula 1-76

[0167] - (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N-(2,2-difluoroethyl)-4-methyl-pent-2- enamide of formula 1-77

[0168] - (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N-hydroxy-N,4-dimethyl-pent-2-enamide of formula 1-78

[0169] - (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N-methoxy-N,4-dimethyl-pent-2-en- amide of formula 1-79

[0170] - (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N,4-dimethyl-pent-2-enamide of formula 1-80

[0171] - (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N-methoxy-4-methyl-pent-2-enamide of formula 1-81

[0172] - (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N,N,4-trimethyl-pent-2-enamide of formula 1-82

[0173] In a particularly preferred embodiment, the compounds I of this invention are selected from the group consisting of 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-11 , 1-12, 1-13, 1-15, 1-16, 1-19, I-22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30, 1-31 , I-32, I-33, I-34, I-35, I-36, I-37, I-38, I-39, I-40, I- 41 , I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-49, 1-51 , I-52, I-53, I-54, I-55, I-57, I-59, I-60, 1-61 , I-62, I-63, I-64, I-65, I-66, I-68, I-70, 1-71 , I-72, I-73, I-74, I-75, I-76, I-77, I-78, I-79, I-80, 1-81 and I-82.

[0174] In an especially preferred embodiment, the compounds I of this invention are selected from the group consisting of 1-1 , I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-9, 1-10, 1-11 , 1-12, 1-13, 1-15, 1-16, 1-19, I-22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30, 1-31 , I-32, I-33, I-34, I-35, I-36, I-37, I-38, I-39, I-40, I- 41 , I-42, I-43, I-44, I-45, I-46, I-47, I-48, I-49, 1-51 , I-52, I-53, I-54, I-55, I-57, I-59, I-60, 1-61 , I-62, I-63, I-64, I-65, I-66, I-68, I-70, 1-71 , I-72, I-73, I-74, I-75 and I-76.

[0175] The 2-phenoxybutanoylamide compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, for example by the following processes. 2-Phenoxybutanoic acids of the formula III or salts thereof can be reacted with the 4-amino-4- methyl-2-pentenoate derivative of formula IV to give the desired 2-Phenoxybutanoylamide compounds of formula I.

[0176] 2-Phenoxybutanoic acids III as used herein are known (e.g., CAS 39644-27-4, 2275149-07-8, 2005615-68-7, 1821838-21-4, 61993-97-3, 2618536-29-9; 68969-28-8) or can be prepared in analogy to known procedures (e.g., W02013122041 ; US4001427; JP2008133218; Journal of the American Chemical Society (2010), 132(3), 1172-1179).

[0177] The 4-amino-4-methyl-2-pentenoate derivatives IV are also known (e.g., CAS 2225181-77-9; 2204271-30-5; 2841734-79-8; 2841913-60-6) or can be prepared according to known procedures (e.g., W02023004376; US20220235007; W02022020150).

[0178] The reaction of the 2-Phenoxybutanoic acids III or salts thereof with the 4-amino-4-methyl-2- pentenoate derivative IV is carried out in the presence of an activating reagent and, if appropriate, in the presence of a base, usually at temperatures of from 0°C to the boiling point of the reaction mixture, preferably at from 0°C to 100°C, particularly preferably at room temperature, in an inert organic solvent [cf. Perich, J. W., Johns, R. B., J. Org. Chem. 53 (17), 4103-4105 (1988); Somlai, C. et al., Synthesis (3), 285-287 (1992); Gupta, A. et al., J. Chem. Soc. Perkin Trans. 2, 1911 (1990); Guan et al., J. Comb. Chem. 2, 297 (2000)]. Suitable activating reagents are condensing agents, such as, for example, polystyrene bound dicyclohexylcarbodiimide, diisopropylcarbodiimide, carbonyldiimidazole, chloroformic esters, such as methyl chloroformate, ethyl chloroform ate, isopropyl chloroformate, isobutyl chloroformate, sec-butyl chloroformate or allyl chloroform ate, pivaloyl chloride, polyphosphoric acid, propanephosphonic anhydride, bis(2-oxo 3-oxazolidinyl)phosphoryl chloride (BOPCI) or sulfonyl chlorides, such as methanesulfonyl chloride, toluenesulfonyl chloride or benzenesulfonyl chloride, or thionylchloride or oxalylchloride. Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons, such as benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF), nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, dimethylformamide (DMF), dimethylacetamide (DMA) and N-methylpyrrolidone (NMP), or else in water; particular preference is given to methylene chloride, tetrahydrofuran (THF), methanol, ethanol and water. It is also possible to use mixtures of the solvents mentioned. Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium 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 carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, N-methyl-morpholine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to sodium hydroxide, triethylamine, ethyldiisopropylamine, N-methylmorpholine and pyridine. The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent. The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use an excess of the 2-Phenoxybutanoic acid III, based on 4-amino-4-methyl-2-pentenoate derivative IV. Workup and isolation of the products can be carried out in a manner known per se.

[0179] 2-phenoxybutanoylamide compounds of formula I according to the invention wherein X is O and R1is H, i.e., 2-phenoxybutanoylamide compounds of formula l.e as shown below can be prepared from the 2-phenoxybutanoylamide compounds of formula l.d (wherein R1is not H) by cleavage of the ester with hydroxide source in a solvent.

[0180] Particular preference as a solvent is given to methylene chloride, tetra hydrofuran (THF), methanol, ethanol and water. It is also possible to use mixtures of the solvents mentioned above. Suitable hydroxide sources are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate; usually at temperatures of from 0°C to the boiling point of the reaction mixture, preferably from 0°C to 100°C, particularly preferably at room temperature.

[0181] To expand the spectrum of activity, prevent herbicidal resistance development and achieve synergistic effects, the compounds of formula (I) may be applied in combination with other herbicides (B). Hence, the present invention additionally provides compositions comprising a compound of formula (I) (component A) and a further herbicidal compound B (component B).

[0182] The following list of herbicides (B) from classes b1) to b15), in conjunction with which the compounds (I) can be used, is intended to illustrate the possible combinations but does not limit them: b1) lipid biosynthesis inhibitors:

[0183] ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxa- prop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pi- noxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop- P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-

[0184] 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-tetra- methyl-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 ,T-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3);

[0185] 5-(Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetra- methyl-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'-bi- phenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-Dichloro -4-cyclopropyl- [1 , 1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1'- biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1 ,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetrame- thyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); and non ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tio- carbazil, triallate and vernolate; b2) acetolactate synthase inhibitors (ALS inhibitors): sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfu- ron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifen- sulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, tri- flusulfuron-methyl and tritosulfuron, imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, ima- zapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsu- lam, pyrimisulfan and pyroxsulam, pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6- dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40- 5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8), sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone; b3) photosynthesis inhibitors: amicarbazone, inhibitors of the photosystem II, e.g. f1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-

[0186] 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl-py- razol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1- methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4- hydroxy-1 ,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5- ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69- 4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1 ,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1), triazine herbicides, including of chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn.hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, met- amitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenyl carbamates such as desmedipham, karbutilat, phen- medipham, phenmedipham-ethyl, nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uraciles such as bromacil, lenacil and terbacil, and bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil and inhibitors of the photosystem I such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate; b4) protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, epyrifenacil, N-ethyl-3-(2,6- dichloro-4-trifluoromethylphenoxy)-5-methyl-1 / 7-pyrazole-1 -carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 / 7-pyrazole-1-carbox- amide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 / 7- pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluo- romethylphenoxy)-5-methyl-1 / 7-pyrazole-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]oxa- zin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-

[0187] 3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4- dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1 / 7-methyl- pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5- fluoro-2-(trifluoromethyl)-1 H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4- dione (CAS 212754-02-4) 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-acetic acid methyl ester (CAS 1970221-16-9), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoro- methyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-py- rimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy] acetic acid ethyl ester (CAS 2158274-50-9), methyl

[0188] 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1 ,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2- pyridyl]oxy]acetate (CAS 2271389-22-9), ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5- oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4), 2-[[3-[[3- chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridi- nyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS 2158275-73-9), 2-[[3-[[3-chloro-6-[3,6- dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyri- dinyl]oxy] acetic acid ethyl ester (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl- 2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methyl- sulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)- acetamide (CAS 2158276-22-1),

[0189] 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro- phenyl]-4,5-dihydro-5-methyl-5-isoxazolecarboxylic acid ethyl ester (CAS 1949837-17-5); b5) bleacher herbicides:

[0190] PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33- 7), rimisoxafen, HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, bipyrazone, fenpyrazone, cypyrafluone, tripyrasulfone, benquitrione, dioxopyritrione; bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-

[0191] 4-(trifluoromethyl)benzamide (CAS 1361139-71-0), bixlozone and 2-(2,5-dichlorophenyl)methyl- 4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7); b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors): glyphosate, glyphosate-isopropylammonium, glyposate-potassium and glyphosate-trimesium (sulfosate); b7) glutamine synthetase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate-ammo- nium; b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors): asulam; b9) mitosis inhibitors: compounds of group K1: dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as ami- prophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlor- thal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham; b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors): chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethena- mid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfen- carbazone, piperophos, pyroxasulfone, dimesulfazet and isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 the isoxazoline compounds of the formula (II) are known in the art, e.g. from WO 2006 / 024820, WO 2006 / 037945, WO 2007 / 071900 and WO 2007 / 096576; b11) cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pen- tafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1); b12) decoupler herbicides: dinoseb, dinoterb and DNOC and its salts; b13) auxinic herbicides;

[0192] 2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, aminocyclopy- rachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammo- nium, 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-butometyl, fluroxypyr-meptyl, halauxifen and its 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, piclo- ram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6); b14) auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium; b15) other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozolin, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tetflupyro- limet, tridiphane, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS 2414510-21-5); including their agriculturally acceptable salts or derivatives.

[0193] Further, it may be useful to apply the compounds of formula (I) in combination with safeners (C). Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the compounds of the formula (I) towards undesired vegetation. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post-emergence application of the useful plant. Hence, the present invention additionally provides compositions comprising a compound of formula (I) (component A) and a safener C (component C).

[0194] Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3- carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro- 5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such amides, esters, and thioesters, provided they have an acid group.

[0195] The following list of safeners (C) in conjunction with which the compounds (I) can be used, is intended to illustrate the possible combinations but does not limit them: benoxacor, cloquintocet, cloquintocet-mexyl, cyprosulfamide, dichlormid, fenchlorazole, fenchlo- razole-ethyl, fenclorim, furilazole, isoxadifen, isoxadifen-ethyl, mefenpyr, mefenpyr-diethyl, naphtalic acid anhydride, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloro-'acetyl)-1,3-oxazolidine (R-29148, CAS 52836-31-4), metcamifen.

[0196] The present invention additionally provides compositions comprising a compound of formula (I) (component A), a herbicide B (component B) and a safener C (component C).

[0197] In the context of the present invention, it is immaterial whether the compound (I) and component B) and / or component C) are applied jointly or separately. In the case of separate application, it is of minor importance, in which order the application takes place. It is only necessary, that the compound (I) and component B) and / or component C) are applied in an effective amount and in a time frame that allows simultaneous action of the Components on the plants, preferably within a timeframe of at most 14 days, in particular at most 7 days, very particular at most 1 day. The compounds B and C described herein may have one or more centers of chirality, in which case they may exist in form of enathiomeric or diastereomeric mixtures and also in form of the pure enantiomers or pure diastereomers. In the compositions described herein it is possible to use the compounds B and C in any of the beforementioned forms. Compounds B and C having double bonds, such as alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond, amide group or a cyclic, non-aromatic moiety, can be used in form of all possible geometrical stereoisomers (cis / trans isomers) as a specific form of diastereomers and mixtures thereof If the compounds B and C have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable salts are those described for compounds (I).

[0198] Examples of particularly suitable salts are listed below:

[0199] In the case of dicamba, suitable salts include those, where the counterion is an agriculturally acceptable cation. For example, suitable salts of dicamba are dicamba-sodium, dicamba-potas- sium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba- N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of a suitable ester are dicamba-methyl and dicamba-butotyl.

[0200] Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammo- nium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isoprop- ylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammo- nium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammo- nium, 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). Examples of suitable esters of 2,4-D are 2,4- D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D- ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D- octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.

[0201] Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB- dimethylammonium. Suitable esters of 2,4-DB are for example 2,4-DB-butyl and 2,4-DB-isoctyl. Suitable salts of dichlorprop are for example dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop- butotyl and dichlorprop-isoctyl.

[0202] Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethyl- ammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA- isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA- olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.

[0203] A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB is MCPB-ethyl.

[0204] Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium. Example of suitable esters of clopyralid is clopyralid-methyl. Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1- methylethyl, wherein fluroxypyr-meptyl is preferred.

[0205] Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable ester of picloram is picloram-isoctyl.

[0206] A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are for example triclopyr-ethyl and triclopyr-butotyl.

[0207] Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA- potassium and 2,3,6-TBA-sodium.

[0208] Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid- dimethylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.

[0209] Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate- trimesium (sulfosate).

[0210] A suitable salt of glufosinate is for example glufosinate-ammonium.

[0211] A suitable salt of glufosinate-P is for example glufosinate-P-ammonium.

[0212] Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil- heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.

[0213] Suitable salts and esters of ioxonil are for example ioxonil-octanoate, ioxonil-potassium and ioxonil-sodium.

[0214] Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop- methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.

[0215] Suitable salts of mecoprop-P are for example mecoprop-P-butotyl, mecoprop-P- dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.

[0216] A suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.

[0217] A suitable salt of naptalam is for example naptalam-sodium.

[0218] Suitable salts and esters of aminocyclopyrachlor are for example aminocyclopyrachlor- dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor- triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium. A suitable salt of quinclorac is for example quinclorac-dimethylammonium.

[0219] A suitable salt of quinmerac is for example quinmerac-dimethylammonium.

[0220] A suitable salt of imazamox is for example imazamox-ammonium.

[0221] Suitable salts of imazapic are for example imazapic-ammonium and imazapic- isopropylammonium.

[0222] Suitable salts of imazapyr are for example imazapyr-ammonium and imazapyr- isopropylammonium.

[0223] A suitable salt of imazaquin is for example imazaquin-ammonium.

[0224] Suitable salts of imazethapyr are for example imazethapyr-ammonium and imazethapyr- isopropylammonium.

[0225] A suitable salt of topramezone is for example topramezone-sodium.

[0226] The active compounds B and C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine [CAS No. 52836-31-4] is also referred to as R- 29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also referred to as AD-67 and MON 4660.

[0227] The present invention additionally provides compositions comprising a compound of formula (I) (component A); optionally a compound selected from a herbicide B (component B) and a safener C (component C); and an auxiliary which is customary for formulating crop protection compounds.

[0228] Compounds (I) and compositions comprising compounds (I) can be converted into the customary agrochemical formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the mixtures according to the present invention. The formulations are prepared in a known manner (cf. US 3,060,084, EP-A 707 445 (for liquid concentrates), Browning: ’’Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147- 48, Perry’s Chemical Engineer’s Handbook, 4th Ed., McGraw-Hill, New York, 1963, S. 8-57 und ff. WO 91 / 13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701, US 5,208,030, GB 2,095,558, US 3,299,566, Klingman: Weed Control as a Science (J. Wiley & Sons, New York, 1961), Hance et al.: Weed Control Handbook (8th Ed., Blackwell Scientific, Oxford, 1989) and Mollet, H. and Grubemann, A.: Formulation technology (Wiley VCH Verlag, Weinheim, 2001).

[0229] The formulations generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, most preferably between 0.5 and 90%, by weight of active substances, which means of compound of formula (I) as the only active substance or of compound of formula (I) together with further active substances. The active substances are employed in a purity of from 90 % to 100 %, preferably from 95 % to 100 % (according to NMR spectrum).

[0230] The agrochemical formulations may also comprise auxiliaries which are customary in agrochemical formulations. The auxiliaries used depend on the particular application form. Examples for suitable auxiliaries are solvents, solid carriers, dispersants or emulsifiers (such as further solubilizers, protective colloids, surfactants and adhesion agents), organic and inorganic thickeners, bactericides, anti-freezing agents, anti-foaming agents, if appropriate colorants and tackifiers or binders (e. g. for seed treatment formulations).

[0231] Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffin, tetrahydronaphthalene, and alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. / V-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.

[0232] Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof. Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (Int. Ed. or North American Ed.). Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and of alkyl naphthalenes, sulfosuccinates, or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids, of oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates. Suitable nonionic surfactants are alkoxylates, / V-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of / V-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters, or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.

[0233] Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.

[0234] Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries, e.g. as listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5. Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazo- linones. Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea, and glycerin. Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants). Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0235] The agrochemical compositions generally comprise between 5 and 99.9 %, preferably between 10 and 99.9 %, more preferably between 30 and 99 %, and in particular between 40 and 90 %, by weight of at least one auxiliary.

[0236] Various types of oils, wetters, adjuvants, fertilizers, or micronutrients, and further pesticides (e.g. fungicides, growth regulators, herbicides, insecticides, safeners) may be added to the compositions described herein as premix, or, not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0237] Examples of formulation types are suspensions (SC, OD, FS), emulsifiable concentrates (EC), emulsions (EW, EO, ES), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG), which can be water-soluble or wettable, as well as gel formulations for the treatment of plant propagation materials such as seeds (GF), herein further below exemplified in detail:

[0238] 1. Composition types for dilution with water i) Water-soluble concentrates (SL, LS)

[0239] 10 parts by weight of compound (I) or composition comprising compound (I) are dissolved in 90 parts by weight of water or in a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. The active substance dissolves upon dilution with water. In this way, a formulation having a content of 10% by weight of active substance is obtained. ii) Dispersible concentrates (DC)

[0240] 20 parts by weight of compound (I) or composition comprising compound (I) are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, e. g. polyvinylpyrrolidone. Dilution with water gives a dispersion. The active substance content is 20% by weight. iii) Emulsifiable concentrates (EC)

[0241] 15 parts by weight of compound (I) or composition comprising compound (I) are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The composition has an active substance content of 15% by weight. iv) Emulsions (EW, EO, ES)

[0242] 25 parts by weight of compound (I) or composition comprising compound (I) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifying machine (Ultraturrax) and made into a ho-mogeneous emulsion. Dilution with water gives an emulsion. The composition has an active substance content of 25% by weight. v) Suspensions (SC, OD, FS)

[0243] In an agitated ball mill, 20 parts by weight of compound (I) or composition comprising compound (I) are comminuted with addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent to give a fine active substance sus-pension. Dilution with water gives a stable suspension of the active substance. The active substance content in the composition is 20% by weight. vi) Water-dispersible granules and water-soluble granules (WG, SG)

[0244] 50 parts by weight of compound (I) or composition comprising compound (I) are ground finely with addi-tion of 50 parts by weight of dispersants and wetting agents and prepared as water- dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance. The composition has an active substance content of 50% by weight. vii) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)

[0245] 75 parts by weight of compound (I) or composition comprising compound (I) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active substance. The active substance content of the composition is 75% by weight. viii) Gel (GF)

[0246] In an agitated ball mill, 20 parts by weight of compound (I) or composition comprising compound (I) are comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance, whereby a composition with 20% (w / w) of active substance is obtained.

[0247] 2. Composition types to be applied undiluted ix) Dustable powders (DP, DS)

[0248] 5 parts by weight of compound (I) or composition comprising compound (I) are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable compo-sition having an active substance content of 5% by weight. x) Granules (GR, FG, GG, MG)

[0249] 0.5 parts by weight of compound (I) or composition comprising compound (I) is ground finely and associ-ated with 99.5 parts by weight of carriers. Current methods are extrusion, spraydrying or the fluidized bed. This gives granules to be applied undiluted having an active substance content of 0.5% by weight. xi) ULV solutions (UL)

[0250] 10 parts by weight of compound (I) or composition comprising compound (I) as described herein are dissolved in 90 parts by weight of an organic solvent, e. g. xylene. This gives a composition to be applied undiluted having an active substance content of 10% by weight.

[0251] The formulation types i) to xi) may optionally comprise further auxiliaries, such as 0,1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1-1 wt% anti-foaming agents, and 0,1-1 wt% colorants.

[0252] For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60 % by weight, preferably from 0.1 to 40 %, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, soaking, as well as in-furrow application methods. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e.g. by seed dressing, pelleting, coating, and dusting.

[0253] Various types of oils, wetters, adjuvants, fertilizers, or micronutrients, and further pesticides (e.g. fungicides, growth regulators, herbicides, insecticides, safeners) may be added to the compounds I or the compositions thereof as premix, or, not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 : 100 to 100: 1 , preferably 1 : 10 to 10: 1.

[0254] The user applies the formulations comprising compounds (I) usually from a pre-dosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the formulation is made up with water, buffer, and / or further auxiliaries to the desired application concentration and the ready-to-use spray liquor. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area. Individual components of the formulation or partially premixed components, e. g. components comprising compounds (I) and optionally compounds B and / or C, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate. It is immaterial whether the compound (I) and compounds B) and / or C) are formulated separately or jointly.

[0255] The compounds of formula (I) or compositions comprising compounds of formula (I) are suitable as herbicides.

[0256] Therefore, the invention further relates to the use of a compound of formula (I) or of compositions comprising a compound of formula (I) for controlling undesired vegetation. The invention additionally relates to a method for controlling undesired vegetation which comprises allowing a herbicidally effective amount of a compound of formula (I) or of compositions comprising a compound of formula (I) to act on plants, their seed and / or their habitat.

[0257] The undesired vegetation can be controlled in a non-crop area or in the cultivation area of a crop, where weeds grow or may grow.

[0258] The term "undesired vegetation" ("weeds") is understood to include any vegetation growing in non-crop-areas or at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired crop (if any). Weeds, in the broadest sense, are plants considered undesirable in a particular location.

[0259] The term "non-crop area" as used herein refers to any area of land that is not used for the cultivation of crops or agricultural production. For example, the compounds of formula (I) or compositions comprising compounds of formula (I) can be used to control weeds and undesired plant growth in turf, lawns, parks, and gardens. They can also be used to maintain vegetation- free areas around roads, railways, sidewalks, and other infrastructure.

[0260] The term "crop cultivation area" as used herein, refers to any land that is used for growing crops, such as fields, gardens, orchards, vineyards, etc. Commonly, herbicides are applied to these areas to control the growth of undesired plants or weeds that can compete with crops for nutrients, water, and sunlight.

[0261] As used herein, the term "an effective amount" refers to the quantity or application rate of the herbicidally active compound(s) that is necessary to achieve the desired effect or result. Hence, this is the amount of the herbicidally active compound(s) that is sufficient to effectively control or eliminate the target weeds or plants, while minimizing any adverse effects on non-target organisms or the environment. The specific effective amount may vary depending on factors such as target plant species, application method, environmental conditions, and the desired level of control.

[0262] The required application rate of the compounds of formula (I) or compositions comprising compounds of formula (I) depends on the density of the undesired vegetation, on the development stage of the plants, on the climatic conditions of the location where the compounds (I) are used and on the application method. In general, the application rate of compounds (I) is from 0.1 to 1000 g / ha, preferably from 1 to 500 g / ha, more preferably from 1 to 250 g / ha, even more preferably from 2 to 100 g / ha of active substance.

[0263] The compounds of formula (I) or compositions comprising compounds of formula (I) can generally be applied for pre-plant burn-down, as pre- or post-emergence treatment of the crop, or together with the seed of a crop plant, preferably as post-emergence treatment.

[0264] As used herein, “pre-plant burndown” refers to the practice of applying a herbicide to a field or area before planting crops. The purpose of pre-plant burndown is to control or eliminate existing weeds or vegetation to create a weed-free environment for the crops. Pre-plant burndown can also help to prevent the development of herbicide-resistant weeds, as it reduces the overall weed seed bank in the soil.

[0265] As used herein, “pre-emergence” refers to an herbicide treatment that is applied to an area before the crop has emerged from the ground or growing medium.

[0266] As used herein, “post-emergence” refers to an herbicide treatment that is applied to an area after the crop has germinated and emerged from the ground or growing medium.

[0267] The compounds of formula (I) or compositions comprising compounds of formula (I) can be applied in conventional manner by using techniques a skilled person is familiar with. Suitable techniques include spraying, atomizing, dusting, spreading or watering. The type of application depends on the intended purpose in a well-known manner; in any case, it should ensure the finest possible distribution of the active ingredients.

[0268] Preferably, the compounds of formula (I) or compositions comprising compounds of formula (I) are applied to an area by spraying, in particular foliar spraying of an aqueous dilution of the active ingredient of the composition. Application can be carried out by customary spraying techniques using, for example, water as carrier and spray liquor rates of from about 10 to 2000 l / ha or 50 to 1000 l / ha, for example from 100 to 500 l / ha. Application by the low-volume and the ultra-low-volume method is possible, as is application in the form of microgranules.

[0269] If the compounds of formula (I) or compositions comprising compounds of formula (I) are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal composition is sprayed, with the aid of the spray apparatus, in such a way that they come into as little contact, if any, as possible with the leaves of the sensitive crop plants while reaching the leaves of undesirable plants which grow underneath, or the bare soil (post-directed, lay-by).

[0270] The compounds of formula (I) or compositions comprising compounds of formula (I) can be also applied by treating seed. The treatment of seeds comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting).

[0271] The term “seed” comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds. The seed used can be seed of the crop plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.

[0272] The compounds of formula (I) or compositions comprising compounds of formula (I) may also be applied in combination with, or by utilizing smart agricultural technologies, such as precision agriculture, remote and proximate imaging and image recognition, or smart agricultural site management programs. These smart agricultural technologies typically include models, e.g. computer programs, that support the user by considering information from a wide variety of sources to increase the quality and yield of harvested material, reduce damage by pests including the prediction of pest pressure and smart application of crop protection products, secure environmental protection, support quick and reliable agronomic decision making, reduce usage of fertilizers and crop protection products, reduce product residues in consumables increase spatial and temporal precision of agronomical measures, automate processes, and enable traceability of measures.

[0273] Commercially available systems which include agronomic models are e.g. FieldScripts™ from The Climate Corporation, Xarvio™ from BASF, AGLogic™ from John Deere, etc.

[0274] Information input for these models include but is not limited to soil data (e.g. pH, organic matter content, moisture level, nutrient content such as nitrogen, potassium, phosphorous and micronutrient content); information on the plants that are currently growing or that may grow at the area of interest including crop plants and / or weeds (e.g. type of plant, chlorophyl levels, biomass, growth stage, plant health, plant water status, plant growth models, genetic traits, biotic damage by infestation or infection with pests, abiotic damage as caused by drought or nutrient stress etc.); weather information (e.g. information on past and present, and forecast of future temperature, humidity, and / or precipitation); information on the location of the area and directly derivable information thereof (e.g. terrain features like altitude, slope, water bodies, sun exposure and hours of sunshine per day, vegetation period, etc.); information on pest pressure (e.g. information of the past or present occurrence of unwanted vegetation, fungal diseases and invertebrate pests at the area of interest, at neighboring areas, the region, or the vegetation zone); information on beneficial organisms (e.g. information of the past or present occurrence of beneficial organisms at the area of interest, at neighboring areas, the region, or the vegetation zone); and I or historic information of any of the aforementioned (e.g. information on previous seasons, or of an earlier point in time of the same season).

[0275] The information usable for precision agriculture may be based on input by at least one user, be accessible from external data sources and databases, or be based on sensor data. Data sources typically include proximate-detection systems like soil-borne sensors and remote sensing as may be achieved by imaging with unmanned airborne vehicles like drones, or satellites. Imaging technologies includes poly- and multispectral imagery in the LIV-VIS, NIR and UV spectrum. Sensors may be included in an Internet-of-Things system and may be directly or indirectly connected to the processing unit, e.g. via a wireless network and / or cloud applications. The information is typically taken into account by at least one processing unit and used to provide recommendations, generate control signals (e.g. for the control of agricultural machinery like tractors, drones, irrigation systems, farm management systems and the like), and / or generate (digital) maps on the area of interest. These (digital) maps contain spatially and optionally temporally resolved information of the agricultural site, wherein the information may contain information directly gathered as described above, combinations thereof or derived thereof, such as pest pressure, nutrient levels, and the like. The recommendations, control signals and (digital) maps may relate to or be used for controlling the application of water, nutrients, agrochemical products, or plant propagation material to the field of interest, or for taking other management measures like tilling, physical or laser-induced weeding.

[0276] Typical technologies that are used in smart agricultural technologies include self-steering robots (such as tractors, harvesters, drones), artificial intelligence (e.g. machine learning), imaging technologies (e.g. image segmentation technologies), big data analysis, and model generation, cloud computing, and machine-to-machine communication.

[0277] Precision agriculture such as precision farming is characterized by spatially and / or temporally resolved, targeted application of active ingredients like pesticides, preferably the compositions according to the present invention, plant-growth-regulators, fertilizers, and / or water including the variation of application rates over the agronomic site, zone or spot application, and of the spatially and / or temporally resolved, targeted planting or seeding of desired plant propagation material to a agronomic site. Precision farming typically includes the use of geo-positioning technologies like GPS for gaining information on the location and boundaries of the area of interest, the utilized application equipment, sensing equipment and recorded data, and to control the actions of farm vehicles such as spraying. By combining geo-positioning data with (digital) maps, it is possible to (semi)-automate agricultural measures at the site of interest, e.g. by using (semi)-autonomous spraying or seeding equipment.

[0278] Precision farming may typically include the application of smart spraying equipment, e.g. spot spraying, and precision spraying at a farm, e.g. by irrigation systems, tractors, robots, helicopters, airplanes, unmanned aerial vehicles, such as drones. Such equipment usually includes input sensors (such as e.g. a camera) and a processing unit configured to analyze the input data and configured to provide a recommendation or decision based on the analysis of the input data to apply the compositions of the invention to the agronomic site, e.g. the soil or to control pests in a specific and precise manner.

[0279] For example, weeds may be detected, identified, and / or classified from imagery acquired by a camera. Such identification and / classification can make use of image processing algorithms, which may utilize artificial intelligence (e.g. machine learning algorithms), or decision trees. In this manner, the combinations or compositions described herein can be applied at the required location, point in time and dose rate.

[0280] The compounds of formula (I) and compositions comprising compounds of formula (I) have an outstanding herbicidal activity against undesired vegetation, i.e. against a broad spectrum of economically important harmful monocotyledonous and dicotyledonous weeds.

[0281] According to one embodiment, the compounds of formula (I) or compositions comprising compounds of formula (I) are used to control monocotyledonous weeds, such as weeds from the genera Hordeum spp., Echinochloa spp., Poa spp., Bromus spp., Digitaria spp., Eriochloa spp., Setaria spp., Pennisetum spp., Eleusine spp., Eragrostis spp., Panicum spp., Lolium spp., Brachiaria spp., Leptochloa spp., Avena spp., Cyperus spp., Axonopris spp., Sorghum spp., and Melinus spp..

[0282] Preferred examples of monocotyledonous weeds on which compounds of formula (I) or compositions comprising compounds of formula (I) act efficiently are selected from the species Hordeum murinum, Echinochloa crus-galli, Poa annua, Bromus rubens L., Bromus rigidus, Bromus secalinus L., Digitaria sanguinalis, Digitaria insularis, Eriochloa gracilis, Setaria faberi, Setaria viridis, Pennisetum glaucum, Eleusine indica, Eragrostis pectinacea, Panicum miliaceum, Lolium multiflorum, Brachiaria platyphylla, Leptochloa fusca, Avena fatua, Cyperus compressus, Cyperus esculentes, Axonopris offinis, Sorghum halapense, and Melinus repens. Especially preferred examples of monocotyledonous weeds on which compounds of formula (I) or compositions comprising compounds of formula (I) act efficiently are selected from the species Echinochloa spp., Digitaria spp., Setaria spp., Eleusine spp. and Brachiarium spp. According to another embodiment, the compounds of formula (I) or compositions comprising compounds of formula (I) are used to control dicotyledonous weeds, such as weeds selected from the genera Amaranthus spp., Erigeron spp., Conyza spp., Polygonum spp., Medicago spp., Mollugo spp., Cyclospermum spp., Stellaria spp., Gnaphalium spp., Taraxacum spp., Oenothera spp., Amsinckia spp., Erodium spp., Erigeron spp., Senecio spp., Lamium spp., Kochia spp., Chenopodium spp., Lactuca spp., Malva spp., Ipomoea spp., Brassica spp., Sinapis spp., llrtica spp., Sida spp, Portulaca spp., Richardia spp., Ambrosia spp., Calandrinia spp., Sisymbrium spp., Sesbania spp., Capsella spp., Sonchus spp., Euphorbia spp., Helianthus spp., Coronopus spp., Salsola spp., Abutilon spp., Vicia spp., Epilobium spp., Cardamine spp., Pieris spp., Trifolium spp., Galinsoga spp., Epimedium spp., Marchantia spp., Solanum spp., Oxalis spp., Metricaria spp., Plantago spp., Tribulus spp., Cenchrus spp. Bidens spp., Veronica spp., and Hypochaeris spp..

[0283] Preferred examples of dicotyledonous weeds on which the compounds of formula (I) or compositions comprising compounds of formula (I) act efficiently are selected from the species Amaranthus spinosus, Polygonum convolvulus, Medicago polymorpha, Mollugo verticillata, Cyclospermum leptophyllum, Stellaria media, Gnaphalium purpureum, Taraxacum offi cinale, Oenothera laciniata, Amsinckia intermedia, Erodium cicutarium, Erodium moschatum, Erigeron bonariensis (Conyza bonariensis), Senecio vulgaris, Lamium amplexicaule, Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoea hederacea, Ipomoea lacunose, Brassica nigra, Sinapis arvensis, Urtica dioica, Amaranthus blitoides, Amaranthus retroflexus, Amaranthus hybridus, Amaranthus lividus, Sida spinosa, Portulaca oleracea, Richardia scabra, Ambrosia artemisiifolia, Calandrinia caulescens, Sisymbrium irio, Sesbania exaltata, Capsella bursa- pastoris, Sonchus oleraceus, Euphorbia maculate, Helianthus annuus, Coronopus didymus, Salsola tragus, Abutilon theophrasti, Vicia benghalensis L., Epilobium paniculatum, Cardamine spp, Pieris echioides, Trifolium spp., Galinsoga spp., Epimedium spp., Marchantia spp., Solanum spp., Oxalis spp., Metricaria matriccarioides, Plantago spp., Tribulus terrestris, Salsola kali, Cenchrus spp., Bidens bipinnata, Veronica spp., and Hypochaeris radicata.

[0284] Especially preferred examples of dicotyledonous weeds on which the compounds of formula (I) or compositions comprising compounds of formula (I) act efficiently are selected from the species Amaranthus spp., Erigeron spp., Conyza spp., Kochia spp. and Abutilon spp.

[0285] If not stated otherwise, the compounds of formula (I) or compositions comprising compounds of formula (I) are suitable for application in any variety of crops as outlined herein.

[0286] According to the invention all the crop plants (cultivated plants) mentioned herein are understood to comprise all species, subspecies, variants and / or hybrids which belong to the respective cultivated plants, including but not limited to winter and spring varieties, in particular in cereals such as wheat and barley, as well as oilseed rape, e.g. winter wheat, spring wheat, winter barley etc.

[0287] For example, corn is also known as Indian corn or maize (Zea mays) which comprises all kinds of corn such as field corn and sweet corn. According to the invention all maize or corn subspecies and / or varieties are comprised, in particular flour corn (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent corn (Zea mays var. indentata), flint corn (Zea mays var. indurata), sweet corn (Zea mays var. saccharata and var. rugosa), waxy corn (Zea mays var. ceratina), amylomaize (high amylose Zea mays varieties), pod corn or wild maize (Zea mays var. tunicata) and striped maize (Zea mays var. japonica). Further, most soybean cultivars are classifiable into indeterminate and determinate growth habit, whereas Glycine soja, the wild progenitor of soybean, is indeterminate (PNAS 2010, 107 (19) 8563-856). The indeterminate growth habit (Maturity Group, MG 00 to MG 4.9) is characterized by a continuation of vegetative growth after flowering begins whereas determinate soybean varieties (Maturity Group, (MG) 5 to MG 8) characteristically have finished most of their vegetative growth when flowering begins. According to the invention all soybean cultivars or varieties are comprised, in particular indeterminate and determinate cultivars or varieties.

[0288] The compounds of formula (I) or compositions comprising compounds of formula (I) are generally suitable for controlling weeds in the following crops:

[0289] Allium cepa (onions), Allium sativum (garlic), Ananas comosus (pineapples), Arachis hypogaea [peanuts (groundnuts)], Asparagus officinalis (asparagus), Avena sativa (oat), Beta vulgaris spec, altissima (sugar beet), Beta vulgaris spec, rapa (turnips), Camellia sinensis (tea plants), Carthamus tinctorius (safflower), Carya illinoinensis (pecan trees), Citrus limon (lemons), Citrus sinensis (orange trees), Coffea arabica, Coffea canephora, Coffea liberica (coffee plants), Cucumis sativus (cucumber), Cynodon dactylon (Bermudagrass), Daucus carota subspec. sativa (carrot), Elaeis guineensis (oil palms), Fragaria vesca (strawberries), Glycine max (soybeans), Gossypium hirsutum, Gossypium arboreum, Gossypium herbaceum, Gossypium viti folium, Hevea brasiliensis (rubber plants), Hordeum vulgare (barley), Humulus lupulus (hops), Ipomoea batatas (sweet potatoes), Juglans regia (walnut trees), Lens culinaris (lentil), Linum usitatissimum (flax), Lycopersicon lycopersicum (tomatoes), Malus spec, (apple trees), Manihot esculenta (cassava), Medicago sativa [alfalfa (lucerne)], Musa spec, (banana plants), Nicotiana tabacum (N.rustica) (tobacco), Olea europaea (olive trees), Oryza sativa (rice), Phaseolus lunatus (limabeans), Phaseolus vulgaris (snapbeans, green beans, dry beans), Picea abies (Norway spruce), Pinus spec, (pine trees), Pistacia vera (pistachio), Pisum sativum (English peas), Prunus avium (cherry trees), Prunus persica (peach trees), Pyrus communis (pear trees), Prunus armeniaca (apricot), Prunus cerasus (sour cherry), Prunus dulcis (almond trees) and prunus domestica (plum trees), Ribes sylvestre (redcurrants), Ricinus communis (castor-oil plants), Saccharum officinarum (sugar cane), Secale cereale (rye), Sinapis alba, Solanum tuberosum (Irish potatoes), Sorghum bicolor (s. vulgare) (sorghum), Theobroma cacao (cacao plants), Trifolium pratense (red clover), Triticum aestivum (wheat), Triticale (triticale), Triticum durum (durum wheat), Triticum turgidum (hard wheat), Triticum spelta (Spelt), Vicia faba (tick beans), Vitis vinifera (grapes), and Zea mays (Indian corn, sweet corn, maize).

[0290] The compounds of formula (I) or compositions comprising compounds of formula (I) are particularly suitable for controlling weeds in the following crops:

[0291] Allium cepa, Allium sativum, Arachis hypogaea, Avena sativa, Beta vulgaris spec, altissima, Cynodon dactylon, Daucus carota subspec. sativa, Glycine max, Gossypium hirsutum, Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium, Hordeum vulgare, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Pisum sativum, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, and Zea mays.

[0292] In a preferred embodiment, the compounds of formula (I) or compositions comprising compounds of formula (I) are used for controlling weeds in turf and in the following crops: cereals, corn (maize), sorghum, rice, peas, Vicia-beans, Phaseolus-beans, peanuts, cotton, potato, sugarbeet, sugarcane, and vegetables In a particularly preferred embodiment, the compounds of formula (I) or compositions comprising compounds of formula (I) are used for controlling weeds in turf and in the following crops: wheat, barley, rye, triticale, oat, corn (maize), sorghum, rice, peas, Vicia-beans, Phaseolus-beans, peanuts, cotton, potato, sugarbeet, sugarcane and vegetables.

[0293] In an especially preferred embodiment, the undesirable vegetation is controlled in cereals. In particular, the cereals are selected from the group comprising wheat, barley, rye, oat, and triticale.

[0294] The compounds of formula (I) or compositions comprising compounds of formula (I), can also be used in crops which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.

[0295] The term "crops" as used herein includes also (crop) plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.

[0296] Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR / Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect. Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.

[0297] Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®. However, most of the herbicide tolerance traits have been created via the use of transgenes.

[0298] Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4- hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione. Transgenes which have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601 , gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.

[0299] Transgenic corn events comprising herbicide tolerance genes are for example, but not excluding others, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHGOJG, HCEM485, VCO- 01981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

[0300] Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS- 81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.

[0301] Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.

[0302] Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

[0303] Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec, and synthetic variants thereof, like cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.1O5, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin have been transferred to other plants. In particular genes coding for protease inhibitors, like CpTI and pinll. A further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes. An example for such a transgene is dvsnf7.

[0304] Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt11 , Bt176, MON801 , MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098.

[0305] Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701 , MON87751 and DAS-81419.

[0306] Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321 , MON531 , MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.

[0307] Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.

[0308] Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.

[0309] Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb- 4, comprised by soybean event IND-00410-5.

[0310] Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions.

[0311] Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art. For example, detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations “International Service for the Acquisition of Agri-biotech Applications (ISAAA)” (http: / / www.isaaa.org / gmapprovaldatabase) and the “Center for Environmental Risk Assessment (CERA)” (htp: / / cera-Qmc.orq / GMCropDatabase), as well as in patent applications, like EP3028573 and W02017 / 011288.

[0312] The use of compounds of formula (I) or compositions comprising compounds of formula (I) on crops may result in effects which are specific to a crop comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.

[0313] Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).

[0314] The preparation of the compounds of formula I is illustrated by examples; however, the subject matter of the present invention is not limited to the examples given.

[0315] Examples

[0316] A. Synthetic examples

[0317] The preparation of compounds of formula (I) is illustrated by the examples below; however, the subject matter of the present invention is not limited to the examples given.

[0318] With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds I. The compounds obtained in this manner are listed in the table I that follows, together with physical data.

[0319] The products shown below were characterized by NMR spectroscopy or the masses ([m / z]) determined by LC-MS spectrometry.

[0320] Example 1: Methyl-(E)-4-[2-(3,5-dichlorophenoxy)butanoylamino]-4-methyl-pent-2-enoate of the formula 1-1 (see Table I below) 2-(3,5-Dichlorophenoxy)butanoic add (CAS39644-27-4) (250mg, 1.00 mmol) was dissolved under nitrogen atmosphere in 15 ml tetra hydrofuran, methyl (E)-4-amino-4-methyl-2-pentenoate hydrochloride (CAS2225181-77-9) (198 mg, 1.10 mmol), 2-chloro-1 -methylpyridinium iodide (307mg, 1.20mmol) and N,N-diisopropylethylamine (389 mg, 3.01 mmol) were added. After stirring for 16 h, 10ml 1 N KHSO4-solution was added and the suspension was extracted with ethyl acetate. Drying, evaporation and subsequent HPLC purification resulted in Metyl-(E)-4-[2- (3,5-dichlorophenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-1 (328 mg, 87% yield) as colorless crystals.

[0321] 1H-NMR (DMSO): 8.10 (s, 2H); 7.20 (s, 1 H); 7.00 (s, 2H); 6.95 (d, 1 H); 5.75 (d, 1 H); 4.60 (t, 1 H); 3.65 (s, 3H); 1.80 (m, 2H); 1.35 (s, 6H); 0.95 (t, 3H)

[0322] Example 2: (E)-4-[2-(3,5-dichlorophenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of the formula I-2 (see Table I below)

[0323] (1-1 ) (I-2)

[0324] Metyl-(E)-4-[2-(3,5-dichlorophenoxy)butanoylamino]-4-methyl-pent-2-enoate (100 mg, 0.267 mmol) was dissolved in 1.5 ml ethanol and lithium hydroxide (24.0 mg, 1.5 mmol) was added. After stirring for 24 h the solvent was evaporated, water added, extracted with dichloromethane, and the aqueous phase acidified with 1 N HCI. After extraction with dichloromethane the organic phase was dried and evaporated, resulting in (E)-4-[2-(3,5-dichlorophenoxy)butanoylamino]-4- methyl-pent-2-enoic acid (50 mg, 52% yield) as colorless crystals.

[0325] 1H-NMR (DMSO): 12.2 (br, 1 H); 8.15 (s, 2H); 7.20 (s, 1 H); 7.00 (s, 2H); 6.90 (d, 1 H); 5.70 (d, 1 H); 4.60 (t, 1 H); 1.80 (m, 2H); 1.35 (s, 6H); 0.95 (t, 3H)

[0326] Table I: Compounds of the formula I. a as shown above wherein the variables X, R1, R3, R4and rac = racemate, 2-S = 2-S configuration at the chiral center, 2-R = 2-R configuration at the chiral center

[0327] B. Use examples The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:

[0328] The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species. For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the test plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients. For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

[0329] Depending on the species, the test plants were kept at 10 - 25°C or 20 - 35°C, respectively. The test period extended over 2 to 4 weeks. During this time, the test plants were tended, and their response to the individual treatments was evaluated.

[0330] Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the test plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 to 89 and a very good herbicidal activity is given at values of at least 90 to 100.

[0331] The test plants used in the greenhouse experiments were of the following species:

[0332] At an application rate of 250 g / ha, the compound I-2 applied by the post-emergence method, showed very good herbicidal activity against ABLITH.

[0333] At an application rate of 125 g / ha, the compound I-35 applied by the post-emergence method, showed good herbicidal activity against ALOMY.

[0334] At an application rate of 250 g / ha, the compounds I-6, I-7, I-8, I-9, 1-10, 1-16, I-25, I-40 and 1-41 applied by the post-emergence method, showed good herbicidal activity against ALOMY.

[0335] At an application rate of 1000 g / ha, the compounds 1-51 and I-55 applied by the postemergence method, showed very good herbicidal activity against ALOMY.

[0336] At an application rate of 125 g / ha, the compounds I-39, I-65, I-66 and I-73 applied by the postemergence method, showed good herbicidal activity against AMARE.

[0337] At an application rate of 125 g / ha, the compounds I-62 and I-64 applied by the postemergence method, showed very good herbicidal activity against AMARE. At an application rate of 250 g / ha, the compounds 1-29 and 1-42 applied by the pre-emergence method, showed good herbicidal activity against AMARE.

[0338] At an application rate of 250 g / ha, the compounds 1-5, 1-11 , I-32 and I-34 applied by the postemergence method, showed good herbicidal activity against AMARE.

[0339] At an application rate of 250 g / ha, the compounds 1-16, 1-19, I-24, I-40, 1-41 , I-42 and I-43 applied by the post-emergence method, showed very good herbicidal activity against AMARE.

[0340] At an application rate of 500 g / ha, the compound I-4 applied by the post-emergence method, showed very good herbicidal activity against AMARE.

[0341] At an application rate of 125 g / ha, the compounds I-60, 1-61 and I-62 applied by the preemergence method, showed good herbicidal activity against APESV.

[0342] At an application rate of 250 g / ha, the compound I-2 applied by the pre-emergence method, showed very good herbicidal activity against APESV.

[0343] At an application rate of 62.5 g / ha, the compound I-3 applied by the post-emergence method, showed very good herbicidal activity against AVEFA.

[0344] At an application rate of 125 g / ha, the compounds 1-1 , I-36, I-37, I-38, I-57, I-65, I-68, I-70, I- 71 , I-72, I-73, I-74 and I-76 applied by the post-emergence method, showed very good herbicidal activity against AVEFA.

[0345] At an application rate of 125 g / ha, the compound I-66 applied by the post-emergence method, showed good herbicidal activity against AVEFA.

[0346] At an application rate of 250 g / ha, the compounds I-2, I-7, I-8, I-9, 1-10, 1-11 , 1-15, I-22, I-24, I- 27, I-28, 1-31 , I-40, 1-41 , I-42, I-43, I-44, I-45, I-46 and I-63 applied by the post-emergence method, showed very good herbicidal activity against AVEFA.

[0347] At an application rate of 250 g / ha, the compounds I-5, I-6, 1-13, 1-16, 1-19, I-23, I-25, I-26, I-29, I-30, I-47 and I-48 applied by the post-emergence method, showed good herbicidal activity against AVEFA.

[0348] At an application rate of 500 g / ha, the compound I-49 applied by the post-emergence method, showed good herbicidal activity against AVEFA.

[0349] At an application rate of 1000 g / ha, the compounds 1-51 , I-52, I-53, I-54 and I-59 applied by the post-emergence method, showed very good herbicidal activity against AVEFA.

[0350] At an application rate of 250 g / ha, the compound I-22 applied by the pre-emergence method, showed very good herbicidal activity against DIGSA.

[0351] At an application rate of 250 g / ha, the compounds I-23, I-24, I-25, I-30 and I-43 applied by the pre-emergence method, showed good herbicidal activity against DIGSA.

[0352] At an application rate of 125 g / ha, the compounds 1-1 and I-57 applied by the pre-emergence method, showed very good herbicidal activity against ECHCG.

[0353] At an application rate of 125 g / ha, the compounds 1-1 and I-76 applied by the post-emergence method, showed very good herbicidal activity against ECHCG.

[0354] At an application rate of 125 g / ha, the compound I-72 applied by the post-emergence method, showed good herbicidal activity against ECHCG.

[0355] At an application rate of 250 g / ha, the compounds I-5, I-6, I-8, I-9, 1-10, 1-11 , 1-12, 1-13, I-22, I- 23, I-24, I-25, I-28, I-30, I-44, I-45 and I-46 applied by the post-emergence method, showed very good herbicidal activity against ECHCG.

[0356] At an application rate of 250 g / ha, the compounds I-2, I-7, 1-15, 1-19, I-27, 1-31 , I-32, I-34 and I-47 applied by the post-emergence method, showed good herbicidal activity against ECHCG. At an application rate of 500 g / ha, the compound 1-4 applied by the post-emergence method, showed very good herbicidal activity against ECHCG.

[0357] At an application rate of 1000 g / ha, the compounds I-53, I-54 and I-59 applied by the postemergence method, showed very good herbicidal activity against ECHCG.

[0358] At an application rate of 62.5 g / ha, the compound I-3 applied by the post-emergence method, showed very good herbicidal activity against LOLMll.

[0359] At an application rate of 62.5 g / ha, the compound I-33 applied by the post-emergence method, showed good herbicidal activity against LOLMll.

[0360] At an application rate of 125 g / ha, the compounds I-38, I-70, 1-71, I-74 and I-76 applied by the post-emergence method, showed very good herbicidal activity against LOLMll.

[0361] At an application rate of 125 g / ha, the compounds I-37 and I-72 applied by the postemergence method, showed good herbicidal activity against LOLMU.

[0362] At an application rate of 250 g / ha, the compounds I-27, I-30 and I-46 applied by the preemergence method, showed very good herbicidal activity against LOLMU.

[0363] At an application rate of 250 g / ha, the compounds I-26, 1-31 and I-47 applied by the preemergence method, showed good herbicidal activity against LOLMU.

[0364] At an application rate of 250 g / ha, the compound I-63 applied by the post-emergence method, showed very good herbicidal activity against LOLMU.

[0365] At an application rate of 1000 g / ha, the compounds 1-51, I-52, I-53, I-54 and I-59 applied by the pre-emergence method, showed very good herbicidal activity against LOLMU.

[0366] At an application rate of 1000 g / ha, the compound I-55 applied by the pre-emergence method, showed good herbicidal activity against LOLMU.

[0367] At an application rate of 62.5 g / ha, the compound I-3 applied by the post-emergence method, showed very good herbicidal activity against POLCO.

[0368] At an application rate of 62.5 g / ha, the compound I-33 applied by the post-emergence method, showed good herbicidal activity against POLCO.

[0369] At an application rate of 125 g / ha, the compounds I-35, I-57, I-60, 1-61, I-62, I-64, I-66, I-68, I- 70 and 1-71 applied by the post-emergence method, showed very good herbicidal activity against POLCO.

[0370] At an application rate of 125 g / ha, the compounds I-36, I-39, I-73, I-74 and I-75 applied by the post-emergence method, showed good herbicidal activity against POLCO.

[0371] At an application rate of 250 g / ha, the compounds I-32 and I-34 applied by the postemergence method, showed good herbicidal activity against POLCO.

[0372] At an application rate of 125 g / ha, the compound I-57 applied by the pre-emergence method, showed very good herbicidal activity against SETFA.

[0373] At an application rate of 125 g / ha, the compound I-75 applied by the post-emergence method, showed good herbicidal activity against SETFA.

[0374] At an application rate of 250 g / ha, the compound 1-1 applied by the pre-emergence method, showed very good herbicidal activity against SETFA.

[0375] At an application rate of 62.5 g / ha, the compound I-33 applied by the post-emergence method, showed good herbicidal activity against SETVI.

[0376] At an application rate of 125 g / ha, the compounds I-37, 1-61 and I-75 applied by the postemergence method, showed very good herbicidal activity against SETVI.

[0377] At an application rate of 125 g / ha, the compounds I-36, I-38 and I-60 applied by the postemergence method, showed good herbicidal activity against SETVI. At an application rate of 250 g / ha, the compounds 1-22, 1-28, 1-43, 1-44, 1-45, 1-46 and 1-47 applied by the pre-emergence method, showed very good herbicidal activity against SETVI.

[0378] At an application rate of 250 g / ha, the compounds 1-27, 1-42 and 1-48 applied by the preemergence method, showed good herbicidal activity against SETVI. At an application rate of 250 g / ha, the compound 1-63 applied by the post-emergence method, showed very good herbicidal activity against SETVI.

[0379] At an application rate of 500 g / ha, the compound 1-49 applied by the pre-emergence method, showed very good herbicidal activity against SETVI.

[0380] At an application rate of 500 g / ha, the compound 1-4 applied by the post-emergence method, showed very good herbicidal activity against SETVI.

[0381] At an application rate of 1000 g / ha, the compounds 1-51, I-53, I-54, I-55 and I-59 applied by the pre-emergence method, showed very good herbicidal activity against SETVI.

[0382] At an application rate of 1000 g / ha, the compound I-52 applied by the pre-emergence method, showed good herbicidal activity against SETVI.

Claims

1. Claims1. A compound of general formula (I)whereinX is O, NH, NCH3, NOCH3, NOH, or S;R1is selected from H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl,C2-Ce-alkynyl, C2-Ce-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkythio-Ci-C4-alkyl, phenyl unsubstituted or substituted by 1 , 2 or 3 halogen atoms, which may be the same or different, or phenylmethylene wherein the phenyl moiety may be substituted by 1 , 2 or 3 halogen atoms, which may be the same or different;R2is H or halogen;R3is selected from halogen, CN, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, or Ci-Ce- haloalkoxy;R4is selected from H, halogen, CN, Ci-Ce-alkyl, Ci-Ce-alkoxy, or Ci-Ce-haloalkoxy;R5is selected from halogen, CN, Ci-Ce-alkyl, C2-Ce-alkynyl, Ci-Ce-haloalkyl, Ci-Ce- alkoxy, or Ci-Ce-haloalkoxy;R6is H or halogen; or agriculturally acceptable salts or stereoisomers thereof.

2. The compound according to claim 1 , wherein X is O, NH, NCH3, NOCH3, or NOH, preferably O or NOCH3.

3. The compound according to claim 1 or 2, wherein R1is selected from H, Ci-Ce-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, or Ci-C4-alkylthio- Ci-C4-alkyl.

4. The compound according to claim 3, wherein R1is selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, 2-propenyl, prop-2-ynyl, 2,2-difluoroethyl, 2-methoxyethyl, or 2- ethylthioethyl.

5. The compound according to any one of claims 1 to 4, wherein R2and R6are both H.

6. The compound according to any one of claims 1 to 5, wherein R3is selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy.

7. The compound according to claim 6, wherein R3is selected from fluoro, chloro, bromo, methyl, difluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy.

8. The compound according to any one of claims 1 to 7, wherein R4is selected from H, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy.

9. The compound according to claim 8, wherein R4is selected from H, fluoro, chloro, bromo, methyl, methoxy, difluoromethoxy, or trifluoromethoxy.

10. The compound according to any one of claims 1 to 9, wherein R5is selected from halogen, CN, Ci-C4-alkyl, C2-C4-alkynyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, or Ci-C4-haloalkoxy.

11. The compound according to claim 10, wherein R5is selected from fluoro, chloro, bromo, CN, methyl, isopropyl, prop-1-ynyl, difluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy.

12. The compound according to any one of claims 1 to 11 , wherein whereinX is O, NH, NCH3, NOCH3, or NOH;R1is selected from H, Ci-Ce-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, or Ci-C4-alkylthio-Ci-C4-alkyl;R2is H;R3is selected from halogen or Ci-C4-alkyl;R4is selected from H, halogen, Ci-C4-alkyl, or Ci-C4-alkoxy;R5is selected from halogen, CN, Ci-C4-alkyl, C2-C4-alkynyl, Ci-C4-haloalkyl, orCi-C4-haloalkoxy;R6is H; or agriculturally acceptable salts or stereoisomers thereof.

13. The compound according to any one of claims 1 to 12, wherein whereinX is O, NH, NCH3, NOCH3, or NOH;R1is selected from H, methyl, ethyl, isopropyl, n-butyl, n-pentyl, 2-propenyl, prop-2- ynyl, 2,2-difluoroethyl, or 2-ethylthioethyl;R2is H;R3is selected from fluoro, chloro, bromo or methyl;R4is selected from H, fluoro, chloro, bromo, methyl, or methoxy;R5is selected from fluoro, chloro, bromo, CN, methyl, isopropyl, prop-1-ynyl, difluoromethyl, difluoromethoxy, or trifluoromethoxy;R6is H; or agriculturally acceptable salts or stereoisomers thereof.

14. The compound according to any one of claims 1 to 13, being selected from the group consisting of the compounds 1-1 to I-82 as listed below:- Methyl-(E)-4-[2-(3,5-dichlorophenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-1- (E)-4-[2-(3,5-dichlorophenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-2- methyl (E)-4-methyl-4-[2-(3,4,5-trichlorophenoxy)butanoylamino]pent-2-enoate of formula 1-3(E)-4-methyl-4-[2-(3,4,5-trichlorophenoxy)butanoylamino]pent-2-enoic acid of formula 1-4- methyl (E)-4-[2-(4-chloro-3,5-dimethyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-5- methyl (E)-4-[2-(3-bromo-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-6- (E)-4-[2-(3-bromo-5-chloro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-7- (E)-4-[2-(3-chloro-4,5-difluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-8- (E)-4-[2-(3-chloro-5-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula I-9- methyl (E)-4-[2-(3-chloro-5-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-10- methyl (E)-4-[2-(3-bromo-5-chloro-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-11- methyl (E)-4-[2-(3-chloro-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-12- methyl (E)-4-[2-(3,5-dimethylphenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-13- methyl (E)-4-[2-(3-fluoro-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-14- methyl (E)-4-[2-(3-cyano-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-15- (E)-4-[2-(3-bromo-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-16- (E)-4-[2-(3-cyano-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-17- (E)-4-[2-(3,5-dimethylphenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula I-- methyl (E)-4-[2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2- enoate of formula 1-19(E)-4-[2-(4-chloro-3,5-dimethyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-20- (E)-4-[2-(3-fluoro-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-21- methyl (E)-4-[2-(3,5-dichloro-4-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula I-22- (E)-4-[2-(3-chloro-5-methyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-23- (E)-4-[2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-24- (E)-4-[2-(3,5-dichloro-4-fluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-25- (E)-4-[2-(4-chloro-3,5-difluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-26- (E)-4-[2-(3-bromo-4,5-difluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-27- methyl (E)-4-[2-(3-bromo-4,5-difluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-28- methyl (E)-4-[2-(4-chloro-3,5-difluoro-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-29methyl (E)-4-[2-(3-chloro-5-cyano-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula 1-30- (E)-4-[2-(3-chloro-5-cyano-phenoxy)butanoylamino]-4-methyl-pent-2-enoic acid of formula 1-31- (E)-4-[[(2S)-2-(3-bromo-5-chloro-phenoxy)butanoyl]amino]-4-methyl-pent-2-enoic acid of formula I-32- (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoic acid of formula I-33- methyl rac-(E)-4-methyl-4-[[rac-(2S)-2-(3-bromo-5-chloro-phenoxy)butanoyl]amino]pent- 2-enoate of formula 1-34- methyl rac-(E)-4-methyl-4-[[rac-(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]pent-2- enoate of formula 1-35(E)-4-methyl-4-[[(2S)-2-(3,4,5-trichlorophenoxy)butanoyl]amino]pent-2-enoic acid of formula 1-36- (E)-4-[[(2S)-2-(3,5-dichloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2-enoic acid of formula 1-37- methyl (E)-4-[[(2S)-2-(3,5-dichloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula 1-38- methyl (E)-4-methyl-4-[[(2S)-2-(3,4,5-trichlorophenoxy)butanoyl]amino]pent-2-enoate of formula 1-39- 2-ethylthioethyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula 1-40- butyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-41pentyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula I-42- prop-2-ynyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-43- isopropyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-44ethyl (E)-4-[[(2S)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula I-45- methyl (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula 1-46- methyl rac-(E)-4-methyl-4-[[rac-(2R)-2-(4-chloro-3,5-dimethyl- phenoxy)butanoyl]amino]pent-2-enoate of formula 1-47methyl rac-(E)-4-methyl-4-[[rac-(2R)-2-(3,5-dichloro-4-methyl- phenoxy)butanoyl]amino]pent-2-enoate of formula 1-48- methyl (E)-4-[[(2R)-2-(3-fluoro-4,5-dimethyl-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula I-49- methyl (E)-4-[[(2R)-2-(4-chloro-3-isopropyl-5-methyl-phenoxy)butanoyl]amino]-4-methyl-- methyl (E)-4-[[(2R)-2-[3-(difluoromethoxy)-5-fluoro-phenoxy]butanoyl]amino]-4-methyl- pent-2-enoate of formula 1-51- methyl (E)-4-[[(2R)-2-(3,5-dichloro-4-methoxy-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula 1-52- methyl (E)-4-[[(2R)-2-(3-chloro-4-fluoro-5-methyl-phenoxy)butanoyl]amino]-4-methyl- pent-2-enoate of formula 1-53- methyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl- pent-2-enoate of formula 1-54- methyl (E)-4-[[(2R)-2-[3-chloro-5-(difluoromethoxy)phenoxy]butanoyl]amino]-4-methyl- pent-2-enoate of formula 1-55- methyl (E)-4-[[(2R)-2-(3-chloro-5-isopropyl-phenoxy)butanoyl]amino]-4-methyl-pent-2-- methyl (E)-4-[[(2R)-2-(4-fluoro-3,5-dimethyl-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula I-57- methyl (E)-4-[[(2R)-2-(3,5-dichloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula 1-58- methyl (E)-4-[[(2R)-2-(3-bromo-4,5-dichloro-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula 1-59methyl (E)-4-[[(2R)-2-(3,5-dimethylphenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula I-60- methyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula 1-61- methyl (E)-4-[[(2R)-2-(3,5-dibromophenoxy)butanoyl]amino]-4-methyl-pent-2-enoate of formula I-62- methyl (E)-4-[[(2R)-2-[3-chloro-5-(trifluoromethoxy)phenoxy]butanoyl]amino]-4-methyl- pent-2-enoate of formula I-63methyl (E)-4-[[(2R)-2-(3,5-dibromo-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula I-64methyl (E)-4-[[(2R)-2-[3,4-dichloro-5-(trifluoromethoxy)phenoxy]butanoyl]amino]-4- methyl-pent-2-enoate of formula 1-65methyl (E)-4-methyl-4-[[(2R)-2-(3,4,5-tribromophenoxy)butanoyl]amino]pent-2-enoate of formula 1-66methyl (E)-4-[2-(3-chloro-5-prop-1-ynyl-phenoxy)butanoylamino]-4-methyl-pent-2-enoate of formula I-67methyl rac-(E)-4-methyl-4-[[rac-(2R)-2-(4-bromo-3,5-dichloro- phenoxy)butanoyl]amino]pent-2-enoate of formula I-68(E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoic acid of formula I-69methyl rac-(E)-4-methyl-4-[[rac-(2R)-2-[3-chloro-5-(difluoromethyl)phenoxy]butanoyl]amino]pent-2-enoate of formula I-70methyl rac-(E)-4-methyl-4-[[rac-(2R)-2-(3,4-dichloro-5-methyl- phenoxy)butanoyl]amino]pent-2-enoate of formula 1-71rac-(E)-4-methyl-4-[[rac-(2R)-2-(3,5-dichloro-4-fluoro-phenoxy)butanoyl]amino]pent-2- enoic acid of formula I-72- ethyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent- 2-enoate of formula 1-73- isopropyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-- prop-2-ynyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4- methyl-pent-2-enoate of formula 1-75allyl (E)-4-[[(2R)-2-(3-bromo-5-chloro-4-fluoro-phenoxy)butanoyl]amino]-4-methyl-pent-2- enoate of formula 1-76- (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N-(2,2-difluoroethyl)-4-methyl-pent- 2-enamide of formula 1-77- (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N-hydroxy-N,4-dimethyl-pent-2- enamide of formula 1-78- (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N-methoxy-N,4-dimethyl-pent-2- enamide of formula 1-79(E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N,4-dimethyl-pent-2-enamide of formula I-80- (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N-methoxy-4-methyl-pent-2- enamide of formula 1-81- (E)-4-[[(2R)-2-(3,5-dichlorophenoxy)butanoyl]amino]-N,N,4-trimethyl-pent-2-enamide of formula I-8215. A composition comprising a compound of formula I or an agriculturally acceptable salt or stereoisomer thereof as defined in any one of claims 1 to 14 and an auxiliary which is customary for formulating crop protection compounds.

16. A method for controlling undesired vegetation which comprises allowing a herbicidally effective amount of a compound of formula I or an agriculturally acceptable salt or stereoisomer thereof as defined in any of claims 1 to 14, or a composition as defined in claim 15 to act on plants, their seed and / or their habitat.

17. Use of a compound of formula I or an agriculturally acceptable salt or stereoisomer thereof as defined in any one of claims 1 to 14, or a composition as defined in claim 15 for controlling undesired vegetation.

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