EP3442978A1

EP3442978A1 - Anellated 3-phenyl tetramic acid derivatives having a herbicidal effect

Info

Publication number: EP3442978A1
Application number: EP17716194.0A
Authority: EP
Inventors: Franz Fenkl; Hendrik Helmke; Andreas REMBIAK; Alfred Angermann; Stefan Lehr; Reiner Fischer; Guido Bojack; Hansjörg Dietrich; Elmar Gatzweiler; Christopher Hugh Rosinger
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2016-04-14
Filing date: 2017-04-06
Publication date: 2019-02-20
Also published as: US20190119298A1; CA3020637A1; UY37203A; AU2017249659A1; JP2019513773A; AU2017249659A8; CN109311903A; EA201892187A1; BR112018071025A2; AR108115A1; WO2017178314A1

Abstract

The present invention relates to new herbicidally active anellated 3-phenyl tetramic acid derivatives according to general formula (I) or agrochemically acceptable salts thereof, and the use of these compounds for controlling weeds and weed grasses in plant crops.

Description

Anellated 3-phenyltetramic acid derivatives with herbicidal action Description

The present invention relates to the technical field of pesticides, in particular that of herbicides for the selective control of weeds and weeds in crops and ornamental garden and general control of weeds and weeds in environmental areas where plant growth is disturbing.

The present invention relates to the provision of new sieve ring-fused 3-phenyltetramic acid derivatives of the general formula (I) or an agrochemically acceptable salt thereof,

and a process for their preparation and their use as herbicidal agents for controlling weeds and grass weeds in crops.

background

It is known that certain 3-phenyltetramic acid compounds possess herbicidal, insecticidal or fungicidal properties which are described, for example, in WO 2001/74770, WO 2006056281, WO 2006056282, WO 2005048710, WO 2005044791, DE 19603332, DE 19935963, US Pat. No. 5,811,374, WO 96 / 35664, WO 99/43649 or WO 2010/102758.

Furthermore, fused 4-phenylpyrazolines are also described, for example, in WO 99/47525 (Pinoxaden).

However, the compounds described in the prior art often have insufficient herbicidal activity and / or insufficient selectivity in crops. The object of the present invention is therefore to provide novel compounds which do not have the disadvantages mentioned.

Detailed description

This object is achieved by new sieve ring-fused 3-phenyltetramic acid derivatives of the general formula (I)

or their agrochemically acceptable salts, in which

X is hydrogen, Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, Ci- C ₃ -

Alkoxy-Ci-C i-alkyl, Ci-C6-haloalkoxy or halogen;

Y is hydrogen, Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, _Ci-C6 alkoxy, C1-C3

Alkoxy-C 1 -C ₄ -alkyl, C 1 -C 6 -haloalkoxy or halogen;

W is hydrogen, Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, _Ci-C6 alkoxy, C1-C3

Alkoxy-C 1 -C ₄ -alkyl, C ₁ -C 6 -haloalkoxy, C ₂ -C 6 -alkenyl, C ₂ -C 6 -alkynyl, halogen or phenyl which is unsubstituted or optionally with one or more substituents independently of one another selected from C3-alkyl, _{Ci-C4-haloalkyl,} C3-C6-cycloalkyl, hydroxy, Ci-C6-alkoxy, Ci-C6-haloalkoxy or halogen may be substituted;

U and V together form a seven-membered ring of the type T'-T ⁴ ,

wherein Z is an oxygen atom, a group -S (O) _n - or a group -IM ^ OR ¹ ) - and n is 0, 1 or 2; R ^{1 is} hydrogen, C ¹ -C ¹ alkyl, C ¹ -C 4 haloalkyl or C ¹ -C 4 alkanoyl;

G is hydrogen, a leaving group L or a cation E, where L is one of the following

R te means

R ^{2 is} C 1 -C ₄ -alkyl or C ₁ -C ₃ -alkoxy-C ₁ -C ₄ -alkyl;

R ^{3 is} C 1 -C ₄ -alkyl;

R ⁴ is C 1 -C 4 -alkyl or phenyl which is unsubstituted or optionally with one or more substituents independently selected from halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy , Nitro or cyano may be substituted;

R ⁵ and R ⁵ 'are each independently methoxy or ethoxy;

R ⁶ and R ^{7 are} each independently methyl, ethyl or phenyl, or together they are

form a saturated 5-, 6- or 7-membered ring or together form a saturated 5-, 6-, or 7-membered heterocycle with an oxygen or sulfur atom; E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent

Aluminum, an ion equivalent of a transition metal, a magnesium-halogen cation or an ammonium ion, wherein optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups Ci-Cs-alkyl, Ci-C6-alkoxy or C3-C7-cycloalkyl are replaced, each mono- or polysubstituted by fluorine, chlorine, bromine, cyano, hydroxy or substituted by one or more oxygen or

Sulfur atoms can be interrupted, or

is a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example, morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated l, 4-diazabicyclo [2.2.2] octane (DABCO) or 1,5-diazabicyclo [4.3.0] undec- 7-en (DBU), or

a heterocyclic ammonium cation is, for example, in each case protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, Pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate, or a sulfonium ion. The compounds of the invention are generally defined by the formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below. The remaining substituents of the general formula (I), which are not mentioned below, have the abovementioned meaning.

A first embodiment of the present invention comprises compounds of the general formula (I) in which

X is preferably hydrogen, C 1 -C -alkyl, C 1 -C -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 3 -alkoxy

Ci-C i-alkyl, Ci-C3-haloalkoxy or halogen, and in which

X is particularly preferably hydrogen, C 1 -C 18 -alkyl, methoxy, ethoxy or halogen.

A second embodiment of the present invention comprises compounds of the general formula (I) in which

Y is preferably _Ci-C4-alkyl, _{Ci-C4-haloalkyl,} Ci-Ce-alkoxy, Ci-C ₃ alkoxy-Ci-C ₄ alkyl,

Ci-C3-haloalkoxy or halogen, in which

Y is particularly preferably C 1 -C 4 -alkyl, methoxy, ethoxy, or halogen.

A third embodiment of the present invention comprises compounds of the general formula (I) in which

W is preferably hydrogen, Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₆ -

Alkoxy, C ₁ -C 3 -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C 6 -haloalkoxy, C ₂ -C -alkenyl, C ₂ -C 6 -alkynyl, halogen or phenyl which is unsubstituted or optionally with one or more substituents independently of one another may be substituted by C ₁ -C ₃ -alkyl, C ₁ -C 4 -haloalkyl, C ₃ -C 6 -cycloalkyl, C ₁ -C 6 -alkoxy, C ₁ -C 6 -haloalkoxy or halogen; and in which

W particularly preferably hydrogen, Ci-C ₄ alkyl, _{Ci-C4-haloalkyl,} Ci-C3-alkoxy,

Methoxy-C ₁ -C ₂ -alkyl, C ₁ -C ₄ -haloalkoxy, C ₂ -C 3 -alkenyl, C ₂ -C 6 -alkynyl, halogen or phenyl which is unsubstituted or optionally with one or more substituents independently selected from methyl , Trifluoromethyl, methoxy, ethoxy, trifluoromethyl and fluorine, chlorine or bromine may be substituted.

A fourth embodiment of the present invention comprises compounds of the general formula (I) in which U and V preferably together form a seven-membered ring of the type T'-T ⁴ ,

wherein Z is an oxygen atom, a group -S (0) _n - or a group -IM ^ OR ¹ ) -, n is 0, 1 or 2, and

R ^{1 is} Ci-C i-alkyl, Ci-C i-haloalkyl or Ci-C i-alkanoyl; and in which

U and V particularly preferably together form a seven-membered ring of the type T ¹ or T,

wherein Z is an oxygen atom, a group -S (0) _n - or a group -N (OCH3) and n is 0, 1 or 2.

A fifth embodiment of the present invention comprises compounds of the general formula (I) in which

G preferably denotes hydrogen, a leaving group L or a cation E, where L is one of the following radicals

R ^{2 is} C 1 -C ₄ -alkyl or C ₁ -C ₃ -alkoxy-C ₁ -C ₄ -alkyl,

R ^{3 is} C 1 -C ₄ -alkyl,

C 1 -C 4 -alkyl or phenyl which is unsubstituted or may optionally be substituted by one or more substituents independently of one another selected from halogen or C 1 -C 1 -alkyl, Methoxy or ethoxy, each independently is methyl, ethyl or phenyl, and

E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent

Aluminum, an ion equivalent of a transition metal, a magnesium-halogen cation or an ammonium ion, wherein optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups Ci-Cs-alkyl, Ci-C6-alkoxy or C3-C7-cycloalkyl are replaced, or

is a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example, morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated l, 4-diazabicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] undec- 7-ene (DBU) or choline; and in which

G particularly preferably hydrogen, a leaving group L or a cation E, wherein L is one of the following radicals

^R: Ci-C ₄ alkyl or Ci-C ₃ alkoxy-Ci-C ₄ alkyl, ^R: is Ci-C i-alkyl, and E is an alkali metal ion, an alkaline earth metal ion equivalent, an ion equivalent

Aluminum, a magnesium-halogen cation or an ammonium ion, in which optionally one, two, three or all four hydrogen atoms substituted by identical or different radicals from the groups Ci-Cs-alkyl, Ci-C6-alkoxy or C3-C7-cycloalkyl or a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated l, 4-diazabicyclo [2.2.2] octane (DABCO), l, 5-diazabicyclo [4.3.0] undec -7-ene (DBU) or choline; and in which

G is most preferably hydrogen, a leaving group L or a cation E, where L is one of the following radicals R is C 1 -C ₄ -alkyl, Methyl or ethyl, and

E is sodium, potassium, an ion equivalent of calcium, magnesium or aluminum.

In the context of the present invention, it is possible to combine the individual preferred, particularly preferred and most preferred meanings for the substituents X, Y, W, U, V, G, R ¹ to R ⁷ and E with one another, where the run number n is 0, 1 or 2. That is, compounds of the general formula (I) are encompassed by the present invention, in which, for example, the substituent X has a preferred meaning and the substituents Y, and W have the general meaning or the substituent X has a preferred meaning which Substituent Y has a particularly preferred or a most preferred meaning and the other substituents have a general meaning.

Two of these combinations of the definitions given above for the substituents X, Y, W, U, V, G, R ¹ to R ⁷ and E, which are particularly preferred, are explained below by way of example and disclosed in each case as further embodiments:

A sixth embodiment of the present invention comprises compounds of the general formula (I) in which

X is hydrogen, Ci-C ₄ alkyl, _{Ci-C4-haloalkyl,} Ci-C ₆ alkoxy, Ci. C ₃ -alkoxy-C ₁ -C ₄ -alkyl,

Ci-C3-haloalkoxy or halogen,

Y _Ci-C4 alkyl, _{Ci-C4-haloalkyl,} Ci-C ₃ _{alkoxy-Ci-C4-alkyl,} _Ci-C3 haloalkoxy or

Halogen is,

Alkoxy-C 1 -C ₄ -alkyl, C ₁ -C 6 -haloalkoxy, C ₂ -C 6 -alkenyl, C ₂ -C 6 -alkynyl, halogen or phenyl which is unsubstituted or optionally with one or more substituents independently of one another selected from C3-alkyl, _{Ci-C4-haloalkyl,} C3-C6-cycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy or halogen may be substituted, in each case together form a seven-membered ring of the type ^Ί ι -Ί ^4, wherein Z is an oxygen atom, a group -S (O) _N - or a group -IM ^ OR ¹ ) -, n is 0, 1 or 2,

R ¹ Ci-C ₄ alkyl, _{Ci-C4-haloalkyl} or Ci-C ₄ alkanoyl,

G is hydrogen, a leaving group L or a cation E, where L is one of the following radicals:

R ^{2 is} C 1 -C ₄ -alkyl or C ₁ -C ₃ -alkoxy-C ₁ -C ₄ -alkyl,

R ^{3 is} C 1 -C ₄ -alkyl, R ^{4 is} C 1 -C ₄ -alkyl or phenyl which is unsubstituted or may optionally be substituted by one or more substituents independently of one another selected from halogen or C 1 -C ₄ -alkyl,

R ⁵ and R ⁵ 'is methoxy or ethoxy,

R ⁶ and R ⁷ each independently represent methyl, ethyl or phenyl, E an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent

Aluminum, an ion equivalent of a transition metal, a magnesium-halogen cation or an ammonium ion, wherein optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups Ci-Cs-alkyl, Ci-C6-alkoxy or C3-C7 cycloalkyl or a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example

Morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or each protonated l, 4-diazabicyclo [2.2.2] octane (DABCO), l, 5-diazabicyclo [4.3.0] undec-7-ene (DBU) or choline means.

A seventh embodiment of the present invention comprises compounds of the general formula (I) in which

X is hydrogen, C 1 -C ₄ -alkyl, methoxy, ethoxy or halogen,

Y is C 1 -C ₄ -alkyl, methoxy, ethoxy, or halogen,

W is hydrogen, Ci-C ₄ alkyl, _{Ci-C4-haloalkyl,} _Ci-C3 alkoxy, methoxy-C ₂ alkyl, Ci-

C _{4 is} haloalkoxy, C ₂ -C 3 alkenyl, C ₂ -C 6 alkynyl, halogen or phenyl; is unsubstituted or may optionally be substituted by one or more substituents independently selected from methyl, trifluoromethyl, methoxy, ethoxy, trifluoromethyl and fluorine, chlorine or bromine,

U and V together form a seven-membered ring of the type T ¹ or T ³ ,

wherein Z is an oxygen atom, a group -S (0) _n - or a group -N (OCH3) and n is 0, 1 or 2. G is hydrogen, a leaving group L or a cation E, where L is one of the following

Leftovers is

R ^{2 is} C 1 -C ₄ -alkyl,

R ^{3 is} methyl or ethyl, and

E is sodium, potassium, an ion equivalent of calcium, magnesium or aluminum.

In the general formula (I) and all subsequent formulas in the present invention, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton may each be straight-chain or branched. Unless specifically stated, these radicals are the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, or in unsaturated groups having 2 to 6 carbon atoms, in particular 2 to 4 carbon atoms, is preferred. Alkyl radicals, including in the composite meanings such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1, 3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; where at least one double bond or triple bond, preferably one double bond or triple bond, respectively, is formed. hold is. Alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1 -yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; Alkynyl includes, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and 1-methyl-but-3-yn-1-yl.

Cycloalkyl groups are, for. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. The cycloalkyl groups can occur in bi- or tri-cyc lischer form.

When haloalkyl groups and haloalkyl groups of haloalkoxy, haloalkenyl, haloalkynyl and the like are mentioned. are indicated in these residues, the lower carbon skeletons, z. B. with 1 to 6 carbon atoms or 2 to 6, in particular 1 to 4 carbon atoms or preferably 2 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton in each case straight-chain or branched. Examples are difluoromethyl, 2,2,2-trifluoroethyl, trifluoroallyl, 1-chloroprop-1-yl-3-yl.

Alkylene groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 10 carbon atoms, in particular 1 to 6 carbon atoms or preferably 2 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton, which may each be straight-chain or branched. Examples are methylene, ethylene, n- and i-propylene and n-, s-, i-, t-butylene. Hydroxyalkyl groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton, which may each be straight-chain or branched. Examples of these are 1, 2-dihydroxyethyl and 3-hydroxypropyl.

Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl, alkenyl and alkynyl are halogen, preferably fluorine, chlorine or bromine, in particular by fluorine and / or chlorine, partially or completely substituted alkyl, alkenyl or alkynyl, for example monohaloalkyl (= monohaloalkyl), perhaloalkyl, CF ₃ , CF ₂ Cl, CHF ₂ , CH ₂ F, CF ₃ CF ₂ , CH ₂ FCHCl, CCI ₃ , CHCl ₂ , CH ₂ CH ₂ Cl; Haloalkoxy is, for example, OCF ₃ , OCHF ₂ , OCH ₂ F, CF ₃ CF ₂ O, OCH ₂ CF ₃ and OCH ₂ CH ₂ Cl; the same applies to haloalkenyl and other halogen-substituted radicals. Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl or naphthyl, preferably phenyl.

The compounds of formula (I) can form salts. Salt formation can be effected by the action of a base on those compounds of the formula (I) which carry an acidic hydrogen atom. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular Alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts, for example with cations of the formula [NRR'R "R"'] ⁺ , wherein R to R'"are each independently one another may represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl, and also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C 1 -C 4) -trialkylsulfonium and (C 1 -C 4) -trialkylsulfoxonium salts.

The compounds of formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 3 PO 4 or HNO 3, or organic acids, e.g. Carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, such as p-toluenesulfonic acid, to a basic group, e.g. Amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion.

Suitable substituents which are in deprotonated form, e.g. Sulfonic acids or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups. Especially for reasons of higher herbicidal activity, better selectivity and / or better manufacturability, compounds of the general formula (I) or their agrochemical salts or quaternary N derivatives of the invention are of particular interest, in which individual radicals are one of those already mentioned or mentioned below have preferred meanings, or in particular those in which one or more of the aforementioned or mentioned below preferred meanings occur in combination.

The general or preferred radical definitions given above are valid both for the end products of the general formula (I) and correspondingly for the starting materials and intermediates required in each case for their preparation. These residue definitions can be interchanged with each other as well as between the specified preferred ranges.

Depending on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and / or optical isomers or mixtures of isomers in different compositions, which can optionally be separated in a customary manner. Both the pure isomers and the tautomeric, isomeric or enantiomeric mixtures, their preparation and use and compositions containing them are the subject of the present invention. However, in the following, for the sake of simplicity, reference will always be made to compounds of the formula (I), although both the pure compounds and optionally mixtures with different proportions of isomeric and tautomeric compounds are meant. Including the meanings described above for the groups T'-T ⁴ , the present invention thus has the following structural types:

(1-1) (1-2) (1-3) (1-4)

The compounds of the general formula (I) according to the invention are prepared on the basis of processes known from the literature, for example by a) if G is a hydrogen atom, precursors of the general formulas (II-1 to II-4)

(IM) (II-2) (II-3) (II-4) in which W, X, Y and Z have the meanings given above and R ^{8 is} Ci-C i-alkyl, preferably methyl or ethyl or for an amino, Ci-C4-alkylamino or C1-C4-dialkylamino group, optionally in the presence of a suitable solvent or

Diluent with a suitable base to give the compound of general formula (I) according to the invention, or b) a compound of general formula (Ia)

in which U, V, W, X and Y each have the meanings given above, with a compound of the general formula (III), Hal-L (III)

in which L has the abovementioned meaning and Hai can be a halogen atom, preferably chlorine or bromine or a sulfonic acid group, if appropriate in the presence of a suitable solvent or diluent and a suitable base, brings to reaction.

The required precursors of the general formula (II-1), (Π-2), (Π-3) and (Π-4) can also be prepared using synthesis methods known from the literature. In Scheme 1, one of the possible procedures for the preparation of the precursors (II-l) and (Π-3) is outlined, wherein the synthesis of the precursors (II-2) and (Π-4) can of course be carried out in a completely analogous manner.

Scheme 1

ίΥΠΐχ

Here, by way of example, a heterocyclic caprolactam of the general formula (IV) is acylated with a phenylacetic acid chloride of the general formula (V) optionally in the presence of a suitable base to give a compound of the general formula (VI), where in each case Z, X, Y and W are those indicated above Have meaning. Suitable bases are, for example, organometallic reagents such as n-butyllithium, s-butyllithium or lithium diisopropylamide. Compounds of type (IV) are known or can be prepared according to known methods. Phenylacetic acids or their chlorides having the general formula (V), in which X, Y and W have the abovementioned meaning, are likewise known from the literature. For relevant methods, see, inter alia, Kobunshi Kagaku 1970, 27 (297), 1-20 or US 2771468 and the patent publications cited at the outset.

For the reaction of the intermediate (VI) to compounds of the type (VII) in which X, Y, W and Z correspond to the definition described above and R ^{9 is} for example a phosphono group such as -PO (OMe) ₂ , -PO (OEt ₂ ) and -PO (OC ₆ H ₅ ) 2 or a sulfonic ester group such as methylsulfonyl, phenylsulfonyl or trifluoromethylsulfonyl, the presence of a suitable base such as, for example, potassium hexamethyldisilazane, n-butyllithium or lithium diisopropylamide may be advantageous. The implementation of such reactions can otherwise be carried out in close accordance with the prior art. Details are given, for example, in J. Org. Chem., 60 (9), 2656-7; 1995 or Bioorg & Med. Chemistry Letters, 17 (21), 5872-5875; 2007); Eur. J. Org. Chem., (7), 1306-1317; 2013; Synlett, (6), 913-916; 2009 or Chem. Commun. 16, 1757-1758; 1998 described.

The precursor of general formula (Π-3) required for process a) is obtained by alkoxycarbonylation of the intermediates of general formula (VII). Such reaction techniques are well known and can be carried out according to methods known in the literature, see, for example, Eur. J. Org. Chem., (7), 1306-1317; 2013 or Synlett, (6), 913-916; In 2009.

For the reduction of precursors of the general formula (Π-3) to the optionally desired precursors having the general formula (II-1) are also a variety of methods known from the literature or reducing agents available. For example, the catalytic hydrogenation with common transition metal catalysts such as palladium or nickel in suitable standard solvents such as methanol, ethanol or ethyl acetate is also obvious.

Sometimes it may be advantageous for the course of the catalytic hydrogenation, when the intermediate of the general formula (Π-3) is first converted with a suitable base in its isomer (VIII) and this is then subjected to the reduction described above.

Rearrangement of the double bond is accomplished by treatment with bases, e.g. Potassium tert-butoxide, Kaliumhexamethyltdisilazid or lithium diisopropylamide, in an inert solvent, preferably at low temperatures by literature methods. For further details on this technique see, for example, J. Am. Chem. Soc., 108 (23), 7373-7377; 1986; U.S. 6413448; Tetrahedron 55 (12), 3791-3802; 199; Tetrahedron, 66 (45), 8605-8614; Of 2010.

Alternatively, the preparation of precursors (II-1) to (Π-4) can also be carried out on the route outlined in Scheme 2 for the case of compounds (II-2) or (Π-4). In this case, starting materials of the general formula (IX), in which Z has the meaning given above, are first converted into compounds of the general formula (X), PG being a suitable NH protective group such as benzyl, benzyloxycarbonyl, phenylcarbamoyl or formyl. These intermediates can then be converted analogously to the methodology described above into the compounds of the general formula (Π-2) and (Π-4).

Scheme 2

The compounds of the formula (I) according to the invention (and / or their salts), together referred to as "compounds according to the invention", have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants which expel from rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.

The present invention therefore also provides a method for controlling undesirable plants or for regulating the growth of plants, preferably in plant crops, wherein one or more compounds of the invention are applied to the plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds) or the area on which the plants grow (eg the acreage) are applied. The compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufverfahren be applied. Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without it being intended to restrict them to certain species.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata , Ishaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis Galinsoga Galium Hibiscus Ipomoea Kochia Lamium Lepidium Lindernia Matricaria Mentha Mercurialis Mullugo Myosotis Papaver Pharbitis Plantago Polygonum Portulaca Ranunculus Raphanus Rorippa Rotala Rumex , Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

If the compounds according to the invention are applied to the surface of the earth before germination, then either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die off completely after a lapse of three to four weeks.

When the active ingredients are applied to the green parts of the plants postemergence, growth stops after the treatment and the harmful plants remain in the growth stage existing at the time of application or die completely after a certain time, so that a weed competition harmful to the crop plants takes place very early and sustainably eliminated.

Although the compounds of the present invention have excellent herbicidal activity against mono and dicotyledonous weeds, crops of economically important crops, e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple, Asparagus , Avena, Hordeum, Oryza, Panicum, Saccharum, Seeal, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, depending on the structure of the respective compound of the invention and their application rate only insignificantly or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in crops such as agricultural crops or ornamental plants.

In addition, the compounds according to the invention (depending on their respective structure and the applied application rate) have excellent growth-regulatory properties in crop plants. They regulate the plant's own metabolism and can thus be used to specifically influence plant ingredients and facilitate harvesting, such as through Triggering of desiccation and stunting are used. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, for example, as a result of which storage formation can be reduced or completely prevented.

Due to their herbicidal and plant growth regulatory properties, the active compounds can also be used for controlling harmful plants in crops by genetic engineering or by conventional mutagenesis of modified plants. The transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.

Preferred with respect to transgenic crops is the use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables. The compounds according to the invention can preferably be employed as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.

Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants. Alternatively, new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). For example, genetic modifications of crop plants have been described in several cases in order to modify the starch synthesized in the plants (eg WO 92/11376, WO 92/14827, WO 91/19806),

transgenic crops which are resistant to certain glufosinate-type herbicides (cf., for example, EP-A-0242236, EP-A-242246) or glyphosates

(WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659)

are resistant, transgenic crops, for example cotton, with the ability

Bacillus thuringiensis toxins (Bt toxins) to produce, which the

Make plants resistant to certain pests (EP-A-0142924, EP-A-0193259).

Transgenic crop plants with modified fatty acid composition (WO 91/13972).

- Genetically modified crops with new content or secondary substances z. B. new

Phytoalexins that cause increased disease resistance (EPA 309862, EPA0464461) genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EPA 0305398).

Transgenic crop plants that produce pharmaceutically or diagnostically important proteins ("molecular pharming")

transgenic crops, which are characterized by higher yields or better quality transgenic crops characterized by a combination of z. B. the o. G. Numerous molecular biological techniques with which new transgenic plants with altered properties can be produced are known in principle, see, for example, BI Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science" 1 (1996) 423-431.) For such genetic manipulations, nucleic acid molecules can be introduced into plasmids that have a mutagenesis or a sequence change by recombination of DNA By means of standard methods it is possible, for example, to carry out base substitutions, to remove partial sequences or to add natural or synthetic sequences For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed. Cold Spring Harbo Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996

The production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product. For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences that have a high degree of homology to the coding sequences of a gene product, but are not completely identical.

In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells.

The transgenic plant cells can be regenerated to whole plants by known techniques. The transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.

Thus, transgenic plants are available which have altered properties by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

Preferably, the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against herbicides, the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.

In the application of the active compounds according to the invention in transgenic crops, in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops. The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants. In a preferred embodiment of the present invention, the compounds of the general formula (I) may also contain such harmful plants, for example from the group Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Digitaria, Echinochloa, Eleusine, Eriochloa, Leptochloa, Lolium , Ottochloa, Panicum, Pennisetum, Phalaris, Poa, Rottboellia, Setaria and / or Sorghum weeds; In particular, Alopecurus, Apera, Avena, Brachiaria, Bromus, Digitaria, Echinochloa, Eriochloa, Lolium, Panicum, Phalaris, Poa, Setaria and / or Sorghum weeds, which are one or more inhibiting the enzyme acetyl-CoA carboxylase (ACCase) Herbicides are resistant. ACCase-inhibiting herbicides include pinoxaden, clodinafop-propargyl, fenoxaprop-P-ethyl, diclofop-methyl, fluazifop-p-butyl, haloxyfop-P-methyl, quizalofop-P-ethyl, propaquizafop, cyhalofop-butyl, clethodim, sethoxydim, Cycloxydim, tralkoxydim or butroxydim are resistant;

and / or are resistant to glyphosate,

and / or against one or more acetolactate synthase (ALS) -inhibiting herbicides such as, for example, one or more sulfonylurea herbicides (eg iodosulfuron-methyl, mesosulfuron-methyl, tribenuron-methyl, triasulfuron, prosulfuron, sulfosulfuron, pyrazosulfuronethyl, bensulfuron-methyl, Nicosulfuron, flazasulfuron, iofensulfuron, metsulfuron-methyl, or any other sulfonylurea disclosed in the "The Pesticide Manual", 15th edition (2009) or 16th edition (2012), CDS Tomlin, British Crop Protection Council and / or one or more triazolopyrimidine herbicides (eg florasulam, pyroxsulam or penoxsulam) and / or one or more pyrimidinyl (thio or oxy) benzoate herbicides (eg bispyribac sodium or pyriftalid) and / or one or more sulfonylamino-carbonyltriazolinone herbicides (eg thiencarbazone) methyl, propoxycarbazone sodium or flucarbazone sodium) and / or imidazolinone herbicides (eg imazamox) Examples of such anti-ACCase and / or ALS inhibitors and / or glyphosate-resistant weeds include Alopecurus myosuroides, Apera spica-venti, Avena fatua, Avena sterilis, Brachiaria decumbens, Brachiaria plantaginea, Digitatia horizontalis, Digitaria insularis, Digitaria sanguinalis , Echinochloa colona, Echinochloa crus-galli, Eleusine indica, Lolium multiflorum, Lolium rigidum, Lolium perenne, Phalaris minor, Phalaris paradoxa, Setaria viridis, Setaria faberi or Setaria glauca.

In a particularly preferred embodiment of the present invention, the compounds of the general formula (I) according to the invention can be used against harmful plants which are resistant to one or more ACCase inhibiting herbicides (eg selected from the list above), at least partially due to mutations (eg Substitution) of one or more amino acids in the ACCase target site of the harmful plant (cf., for example, SB Powles and Qin Yu, "Evolution in Action: Plants Resistant to Herbicides", Annu. Rev. Plant Biol., 2010, 61, pp. 317-347); and or

which are resistant to glyphosate, at least in part due to mutation (e.g., substitution) of one or more amino acids on the EPSPS target site in the particular weed to which glyphosate is targeted; and or

which are resistant to one or more ALS-inhibiting herbicides (eg selected from the above list of ALS-inhibiting herbicides), at least in part due to mutations (eg substitution) of one or more amino acids in the ALS target site in the particular weed (cf. eg SB Powles and Qin Yu, "Evolution in Action: Plants Resistant to Herbicides", Annu., Rev. Plant Biol., 2010, 61, pp. 317-347); and or

which are resistant to one or more ACCase-inhibiting herbicides (eg selected from the list above) and / or to glyphosate and / or to one or more ALS-inhibiting herbicides (eg selected from the list above), at least partially by a metabolite conditional herbicide resistance, e.g. At least in part by a cytochrome P450-mediated metabolism (see, for example, SB Powles and Qin Yu, "Evolution in Action: Plants Resistant to Herbicides", Annu., Rev. Plant Biol., 2010, 61, pp. 317-347). ,

The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations. The invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.

The compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil in water and water in oil emulsions, sprayable solutions, suspension concentrates (SC), Oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water dispersible granules (WG), water soluble Granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in: Winnacker Kuchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973, K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London. The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in Watkins, Handbook of Insecticides Dust Diluents and Carriers, 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen, "Introduction to Clay Colloid Chemistry, 2nd Ed., J. Wiley & Sons, NY, C. Marsden, "Solvents Guide", 2nd Ed., Interscience, NY 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ , Sisley and Wood, "Encyclopaedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964, Schonfeldt, "Border-Active Ethylene Oxide Adducts", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.

On the basis of these formulations, combinations with other pesticidally active substances, e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix. Suitable safeners are e.g. Mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichloromid.

Injectable powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent, dispersant) in addition to a diluent or inert substance, e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ethersulfate, alkanesulfonates, alkylbenzenesulfonates, lignosulfonate sodium, 2,2 'dinaphthylmethane 6,6' disulfonic acid sodium, dibutylnaphthalene sulfonic acid sodium or oleoylmethyltaurine acid. To prepare the wettable powders, the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.

Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers). Examples of emulsifiers which may be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide ethylene oxide

Condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or Polyoxethylensorbitanester such as Polyoxyethylensorbitanfettsäureester. Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water or oil based. They can be prepared, for example, by wet milling using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.

Emulsions, e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as those described e.g. listed above for the other formulation types.

Granules can either be prepared by atomizing the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired when mixed with fertilizers. Water-dispersible granules are generally prepared by the usual methods such as spray-drying, fluidized-bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.

For the preparation of plates, fluidized bed, extruders and spray granules, see e.g. Methods in "Spray Drying Handbook" 3rd Ed. 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq., "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw Hill, New York 1973, p. 8 57.

For further details on the formulation of crop protection agents see, e.g. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81,996 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

As a rule, the agrochemical preparations contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention. In wettable powders, the active ingredient concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation constituents. In the case of emulsifiable concentrates, the active substance concentration may be about 1 to 90, preferably 5 to 80,% by weight. Contain dusty formulations

1 to 30 wt.% Active ingredient, preferably usually 5 to 20 wt.% Of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt.% Active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used. In the case of the water-dispersible granules, the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active ingredient formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and viscosity-influencing agents.

On the basis of these formulations, combinations with other pesticidally active substances, e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix.

For use, the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use.

With the external conditions such as temperature, humidity, the type of herbicide used, inter alia, the required application rate of the compounds of the formula (I) varies. It can vary within wide limits, for example between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha. The following examples illustrate the preparation of the compounds according to the invention:

A. Chemical examples

Example Ia-1-3

8- (2,6-diethyl-4-methylphenyl) -9-hydroxy-1,4,5,9a-tetrahydropyrrolo [1,2-d] [1,4-oxazepine-7 (2H) -one

Example Ia-1-3

0.4 g (3.6 mmol) of potassium tert-butoxide are dissolved in 12 ml of DMF and are added dropwise within 60 min at 70 ° C. to a solution of 0.50 g (1.4 mmol) of methyl 4- [ (2,6-diethyl-4-methylphenyl) acetyl] - l, 4-oxazepan-5-carboxylate in 12 mL of DMF. The mixture is stirred for 10 min at 70 C and follows the course of the reaction via HPLC control. Subsequently, it is stirred with 100 ml of ice water and adjusted to pH = 1 with 2N hydrochloric acid. After distilling off the solvent, the residue is stirred with 15 ml of water and 100 ml of dichloromethane and the organic phase is separated off. Drying over sodium sulfate and distilling off the solvent gives 0.43 g of the title compound.

Analogously to Example Ia-1-3, the following compounds according to the invention were prepared: TABLE 1

Table 2

hl Example Ib-1-1:

8- (2,6-diethyl-4-methyrphenyl) -7-oxo-1,2,4,5,7,9a-hexahydropyrrolo | T, 2-d1-T, 4 ^" | oxazepine-9-ylmethyl carbonate

0.32 g (1.01 mmol) of 8- (2,6-diethyl-4-methylphenyl) -9-hydroxy-1,4,5,9a-tetrahydropyrrolo [1,2-d] [1,4] oxazepine -7 (2H) -one (Example Ia-1-3) are initially charged in 30 mL dichloromethane and treated with 0.41 g (4.1 mmol) of triethylamine. At room temperature, 0.11 g (1.1 mmol) of methyl chloroformate are added and stirred at this temperature for 20 h. Subsequently, 10 mL of water are added and the organic phase is separated off. Drying (sodium sulfate), distilling off the solvent and chromatography on silica gel gives 0.31 g of the title compound as a light yellow oil.

Analogously to Example Ib-1-1, the following compounds according to the invention were prepared: TABLE 4

Table 5

Table 6

Preparation of precursors II

4 - one 4-oxazepan-5 [(2,6-diethyl-4-methylphenyl) acetyl] -l,

4.0 g (34.7 mol) of 1,4-oxazepan-5-one (CAS: 10341-26-1) are dissolved in 150 ml of THF and 1.0 part of n-butyllithium is added dropwise below -70.degree. The mixture is stirred for 20 min and then within 20 min at this temperature dropwise a solution of 7.2 g (31.9 mmol) of [2,6-diethyl-4-methyl-phenyl] acetic acid chloride, stirred for a further 20 min this temperature and another hour at room temperature. For workup, 100 ml of 5% sodium bicarbonate solution and 500 ml of diethyl ether are added, the organic phase is separated off and the aqueous phase is extracted twice with 200 ml of diethyl ether each time. The combined organic phases are saturated with 100 ml. Sodium chloride solution, dried over sodium sulfate and concentrated. Column chromatographic purification of the residue gives 8.30 g of the target product as a crystalline solid with mp. 74 ° C.

4 - [(2,6-diethyl-4-methylphenyl) acetyl] -2,3,4,7-tetrahydro-l, 4-oxazepin-5-yl-diphenyl phosphate

8.2 g (27.0 mmol) of the above compound are initially charged in 250 ml of THF and treated dropwise within one hour below -70 ° C with 6.47 g (1.2 eq) of potassium hexamethyldisilazide in 50 ml of THF. The mixture is stirred for 90 min and below -70 ° C., a solution of 8.71 g (32.4 mmol) of diphenylchlorophosphate in 50 ml of THF is added dropwise. After 60 min at this temperature, allowed to come to room temperature and stirred with 93 mL of 5% sodium hydroxide solution, extracted three times with 100 mL of diethyl ether and once with sat. Sodium chloride solution. After drying over sodium sulfate and distilling off the solvent, the resulting semicrystalline residue is purified by chromatography on silica gel. This gives 10.6 g of the target product in the form of colorless crystals with mp. 110-112 ° C. Methyl 4 - [(2,6-diethyl-4-methylphenyl) acetyl] -2,3,4,5-tetrahydro-l, 4-oxazepin-5-carboxylate

10.5 g (19.6 mmol) of 4 - [(2,6-diethyl-4-methylphenyl) acetyl] -2,3,4,7-tetrahydro-1,4-oxazepin-5-yl-diphenylphosphate are dissolved in 200 ml of DMF, degassed in vacuo and overlaid with argon. Add 0.44 g (0.1 eq) of palladium acetate and 1.0 g (0.2 eq) of triphenylphosphine, overlaid with

Carbon monoxide and stirred for 30 min at room temperature, whereby the solution turns black. Then it is briefly degassed, with 4.0 g (39.2 mmol) of triethylamine and 25.8 g (0.8 mol) of methanol, overlaid again with carbon monoxide and stirred for 60 min at 45 ° C. Thereafter, the reaction solution is poured onto ice-water and the aqueous phase extracted three times with 300 ml of diethyl ether, with 100 ml of sat. Sodium chloride solution, dried over sodium sulfate and concentrated. This gives 2.6 g of a pale yellow oil, which is dissolved in 40 ml of THF and added dropwise at -70 ° C within one hour to a solution of 0.38 g (2.7 mmol) of potassium tert-butoxide in 20 ml of THF , The mixture is stirred for a further 10 minutes at this temperature and then 10 ml of a 1 molar buffer solution (pH = 4.65), allowed to come to room temperature and mixed with about 20 ml of water. The aqueous phase is extracted twice with 50 ml of diethyl ether, with 20 ml of sat. Washed sodium chloride solution, dried over sodium sulfate and concentrated. The column-chromatographic purification of the residue gives 0.32 g of the target product as a yellowish oil.

Methyl 4 - [(2,6-diethyl-4-methylphenyl) acetyl] -l, 4-oxazepan-5-carboxylate

0.50 g (1.4 mmol) of the precursor are hydrogenated in 50 mL of methanol after addition of palladium / carbon (5%) for about 90 minutes at room temperature and atmospheric pressure. After filtering off and distilling off the solvent, the target compound is obtained without further purification as a colorless oil in almost quantitative yield. Benzyl-5-oxo-l, 4-oxazepan-4-carboxylate

5.0 g (43.4 mol) of 1,4-oxazepan-5-one (CAS: 10341-26-1) are dissolved in 100 ml of THF and 1.1 parts of n-butyllithium are added dropwise below -70.degree. The mixture is stirred for 30 min and added 7.8 g (46.0 mmol) of benzyloxycarbonyl chloride dropwise, stirred for 1 h at -70 C and then warmed to RT. For working up, 100 ml of saturated NrLCl solution are added and the mixture is extracted three times with ethyl acetate. The combined organic phases are saturated with 100 ml. Sodium chloride solution, dried over sodium sulfate and concentrated. Column chromatographic purification of the residue gives 10.0 g of the target product as a colorless oil.

Benzyl-5-diphenoxyphosphoryloxy-3,7-dihydro-2H-l, 4-oxazepine-4-carboxylate

10.0 g (40.1 mmol) of the above compound are initially charged in 370 ml of THF and treated dropwise within one hour below -70 ° C with 9.604 g (1.2 eq) of potassium hexamethyldisilazide in 50 ml of THF. The mixture is stirred for 90 minutes and below -70 ° C., a solution of 12.9 g (48.1 mmol) of diphenylchlorophosphate in 75 ml of THF is added dropwise. After 60 min at this temperature, allowed to come to room temperature and stirred with 130 mL of 5% sodium hydroxide solution, the volatiles removed and extracted three times with 100 mL of diethyl ether and once with sat. Sodium chloride solution. After drying over sodium sulfate and distilling off the solvent, the residue obtained is purified by chromatography on silica gel. This gives 15.9 g of the target product as a pale yellow oil. 04-benzyl-05-methyl-3,5-dihydro-2H-l, 4-oxazepin-4,5-dicarboxylate

15.9 g (33.0 mmol) of the above precursor are dissolved in 340 ml of DMF, degassed in vacuo and overlaid with argon. Add 0.74 g (0.1 eq) of palladium acetate and 1.7 g (0.2 eq) of triphenylphosphine, overlaid with carbon monoxide and stirred for 30 minutes at room temperature, whereby the solution turns black. The mixture is then degassed briefly, with 6.7 g (66.1 mmol) of triethylamine and 42.4 g (1.3 mol) of methanol, overlaid again with carbon monoxide and stirred for 60 min at 45 ° C. Thereafter, the reaction solution is poured onto ice-water and the aqueous phase extracted three times with 300 ml of diethyl ether, with 100 ml of sat. Sodium chloride solution, dried over sodium sulfate and concentrated. After chromatography on silica gel, 6.0 g of the target compound are obtained in the form of a yellow oil.

Methyl-l, 4-oxazepan-5-carboxylate

12.3 g (42.2 mmol) of the precursor are hydrogenated in 150 ml of methanol after addition of palladium / carbon (10% strength) for about 3 hours at room temperature and normal pressure. After filtering off and distilling off the solvent, the target compound without further purification as a colorless oil in almost quantitative yield, δ (400 MHz, CDC1 ₃ ) = 1.82-1.87 (m, 1H), 2.08-2.29 (m, 1H), 2.59 -2.64 (m, 1H), 2.90-2.94 (m 1H), 3.49-3.58 (m, 3H), 3.62 (s, 3H), 3. 68 (t, 2H) 4-methyl-phenyl) -acetyl] -l, 4-oxazepan-5-carboxylate

1.1 g (4.1 mmol) of 2- (2-bromo-6-ethyl-4-methylphenyl) acetic acid are dissolved in 20 ml of dichloromethane and admixed dropwise with 1.1 g (2.0 eq.) Of oxalyl chloride after addition of a few drops of dimethylformamide. After completion of the gas evolution, the volatiles are removed completely in vacuo, the residue taken up again in 20 mL of dichloromethane and added to a suspension of 0.65 g (4.1 mmol) of methyl-l, 4-oxazepan-5-carboxylate and 1.70 g (4.0 eq). Triethylamine in 20 mL dichloromethane at 0 ° C added dropwise. After 3 h at RT, water is added, the phases are separated and the organic phase is concentrated. After chromatography on silica gel, 1.05 g of the target compound are obtained as a colorless oil.

Analogously to the preparation of the precursors II-1 -3 and II-1 -10, the following precursors according to the invention were prepared:

Table 7

Table 8

Table 9 B. Formulation Examples a) A dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and / or salts thereof and 90 parts by weight of talc as an inert substance and comminuting in a hammer mill. b) A water-dispersible, wettable powder is obtained by 25

Parts by weight of a compound of the formula (I) and / or salts thereof, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight

mix oleoylmethyl tauric acid sodium as a wetting agent and dispersant and mill in a pin mill. c) A dispersion concentrate which is readily dispersible in water is obtained by dissolving 20 parts by weight of a compound of the formula (I) and / or its salts with 6 parts by weight

Alkylphenolpolyglykolether (®Triton X 207), 3 parts by weight of isotopecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 C) mixed and milled in a ball mill to a fineness of less than 5 microns. d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or its salts, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight

ethoxylated nonylphenol as emulsifier. e) A water-dispersible granules are obtained by

75 parts by weight of a compound of the formula (I) and / or salts thereof,

10 parts by weight of lignosulfonic acid calcium,

5 parts by weight of sodium lauryl sulfate,

3 parts by weight of polyvinyl alcohol and

7 parts by weight kaolin

milled, ground on a pin mill and granulated the powder in a fluidized bed by spraying water as Granulierflüssigkeit. f) A water-dispersible granules are also obtained by

25 parts by weight of a compound of the formula (I) and / or salts thereof,

5 parts by weight of 2,2 'dinaphthylmethane 6,6' disulfonic acid sodium

2 parts by weight of oleoylmethyltaurine sodium,

1 part by weight of polyvinyl alcohol,

17 parts by weight of calcium carbonate and

50 parts by weight of water Homogenized on a colloid mill and pre-crushed, then grinded on a bead mill and the suspension thus obtained in a spray tower by means of a Einstoffdüse atomized and dried.

C. Biological data

1. Herbicidal action or crop plant compatibility in the pre-emergence

Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam in wood fiber pots and covered with soil. The compounds of the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent applied.

After the treatment, the pots are placed in the greenhouse and under good

Maintained growth conditions for the test plants. The visual assessment of the damage to the test plants is carried out after a trial period of 3 weeks in comparison to untreated controls (herbicidal action in percent (%)): 100% action = plants have died, 0% effect = like control plants).

Unwanted plants / weeds:

ALOMY: Alopecurus myosuroides

AVEFA: Avena fatua

CYPES: Cyperus esculentus ECHCG: Echinochloa crus-galli

LOLMU: Lolium multiflorum

SETVI: Setaria viridis Table 10: Pre-run effect

O

dosage

Example no.

[G / ha]

Ib-3-13 320 100 90 100 100 100 lb-3-16 320 90 80 90 90

As the results of Table 10 show, compounds of the present invention have good herbicidal pre-emergence activity against a broad spectrum of grass weeds and weeds. For example, Compounds Nos. Ia-1-AO1LMY, Ia-1-2, Ia-1-4, Ib-1-1, Ib-1-2, and Ib-1-9 and at an application rate of 320 g / each have an 80-100% action against Alopecurus

AAVEF

myosuroides, Avena fatua, Cyperus esculentus, Echinochloa crus-galli, Lolium multiflorum and Setaria viridis. The compounds according to the invention are therefore suitable in the pre-emergence method for controlling unwanted plant growth. O LLMU

^S ETV ^I

2. Herbicidal action or crop plant compatibility postemergence

Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam soil in wood fiber pots, covered with soil and in the greenhouse under good conditions

Growth conditions attracted. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage. In the form of wettable powders (WP) or as

Emulsionskonzentrate (EC) formulated compounds of the invention are then sprayed as an aqueous suspension or emulsion with a water application rate of 600 to 800 1 / ha with the addition of 0.2% wetting agent on the green parts of plants. After about 3 weeks life of the test plants in the greenhouse under optimal growth conditions, the effect of the preparations is scored visually in comparison to untreated controls (herbicidal action in percent (%)): 100% action = plants are dead, 0% effect = like control plants) , Table 11: Tracking efficiency

As the results from Table 11 show, compounds of the invention have good post-emergence herbicidal activity against a broad spectrum of grass weeds and weeds. For example, compounds Nos. Ia-2-1, Ia-2-2, Ib-1-1, Ib-1-2, Ib-1-3, Ib-1-4, Ib-1-6 and Ib- 1-7 at an application rate of 320 g / ha each 90-100% action against Alopecurus myosuroides, Avena fatua, Echinochloa crus-galli, Lolium multiflorum and Setaria viridis. The compounds according to the invention are therefore suitable postemergence for controlling unwanted plant growth.

Claims

claims

1. Compounds of the general formula (I)

or their agrochemically acceptable salts, in which

X is hydrogen, Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, Ci-C3-alkoxy-Ci-C4-alkyl, Ci-C6-haloalkoxy or Halogen is;

Y is hydrogen, Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, Ci-C3-alkoxy-Ci-C4-alkyl, Ci-C6-haloalkoxy or Halogen is;

W is hydrogen, Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, Ci-C ₃ _{alkoxy-Ci-C4-alkyl,} Ci-Ce- Haloalkoxy, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, halogen or phenyl which is unsubstituted or optionally with one or more substituents independently of one another selected from C ₁ -C ₃ -alkyl, C ₁ -C 4 -haloalkyl, C3-C6-cycloalkyl, hydroxy, Ci-C6-alkoxy, Ci-C6-haloalkoxy or halogen may be substituted;

U and V together form a seven-membered ring of the type T'-T ⁴ ,

wherein Z is an oxygen atom, a group -S (O) _n - or a group -IM ^ OR ¹ ) -; n is 0, 1 or 2;

R ₄ alkyl, Ci-C ₄ haloalkyl or Ci-C ₄ alkanoyl ¹ is hydrogen, Ci-C; Hydrogen, a leaving group L or a cation E, where L is one of the following radicals R ^{2 is} C 1 -C ₄ -alkyl or C ₁ -C ₃ -alkoxy-C ₁ -C ₄ -alkyl;

R ^{3 is} C 1 -C ₄ -alkyl;

R ⁴ is C ₁ -C 4 -alkyl or phenyl which is unsubstituted or optionally with one or more substituents independently of one another selected from halogen, C ₁ -C 4 -alkyl, C ₁ -C 4 -haloalkyl, C ₁ -C 4 -alkoxy, C ₁ -C 4 -alkoxy Haloalkoxy, nitro or cyano may be substituted;

R ⁵ and R ⁵ 'are each independently methoxy or ethoxy;

R ⁶ and R ^{7 are} each independently methyl, ethyl or phenyl or

together form a saturated 5-, 6- or 7-membered ring or together form a saturated 5-, 6-, or 7-membered heterocycle with an oxygen or sulfur atom;

E is an alkali metal ion, an ionic equivalent of an alkaline earth metal, an ionic equivalent of aluminum, an ionic equivalent of a transition metal, a magnesium-halogenated cation or an ammonium ion, optionally having one, two, three or all four hydrogen atoms represented by the same or different radicals from the groups C1 C 5 -alkyl, C 1 -C 6 -alkoxy or C 3 -C 7 -cycloalkyl, each of which may be mono- or polysubstituted by fluorine, chlorine, bromine, cyano, hydroxyl or interrupted by one or more oxygen or sulfur atoms, or

is a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated l, 4-diazabicyclo [2.2.2] octane (DABCO) or l, 5-diazabicyclo [4.3.0] undec- 7-en (DBU), or

a heterocyclic ammonium cation is, for example, in each case protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, Pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate, or is a sulfonium ion. Compounds of general formula (I) according to claim 1, characterized in that X is hydrogen, Ci-C ₄ alkyl, _{Ci-C4-haloalkyl,} Ci-C ₆ alkoxy, Ci- C ₃ _{alkoxy-Ci-C4-} -Alkyl, Ci-C3-haloalkoxy or halogen.

Compounds of general formula (I) according to claim 1 or 2, characterized in that Y _Ci-C4 alkyl, _{Ci-C4-haloalkyl,} Ci-C ₃ alkoxy-Ci-C ₄ -alkyl, C ₃ Haloalkoxy or halogen.

Compounds of general formula (I) according to claims 1 to 3, characterized in that W is hydrogen, Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, C - C3-alkoxy-C 1 -C ₄ -alkyl, C ₁ -C 6 -haloalkoxy, C ₂ -C 6 -alkenyl, C ₂ -C 6 -alkynyl, halogen or phenyl which is unsubstituted or optionally selected independently with one or more substituents from Ci-C3 alkyl, _{Ci-C4-haloalkyl,} C3-C6-cycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy or halogen may be substituted.

Compounds of general formula (I) according to Claims 1 to 4, characterized in that U and V in each case together form a seven-membered ring of the type T'-T ⁴ ,

R ^{1 is} C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkanoyl.

Compounds of the general formula (I) according to Claims 1 to 5, characterized in that G is hydrogen, a leaving group L or a cation E, L being one of the following radicals

R ^{2 is} C 1 -C ₄ -alkyl or C ₁ -C ₃ -alkoxy-C ₁ -C ₄ -alkyl,

R ^{3 is} C 1 -C ₄ -alkyl, R ⁴ is C ₁ -C 4 -alkyl or phenyl which is unsubstituted or may optionally be substituted by one or more substituents independently of one another selected from halogen or C ₁ -C 4 -alkyl,

R ⁵ and R ^{5 are} methoxy or ethoxy,

R ⁶ and R ^{7 are} each independently methyl, ethyl or phenyl, and

E is an alkali metal ion, an ionic equivalent of an alkaline earth metal, an ionic equivalent of aluminum, an ionic equivalent of a transition metal, a magnesium-halogen cation or an ammonium ion optionally having one, two, three or all four hydrogen atoms represented by identical or different radicals from the groups C1 C5-alkyl, Ci-C6-alkoxy or C3-C7-cycloalkyl, or is a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or respectively protonated l, 4-diazabicyclo [2.2 .2] octane (DABCO), 1,5-diazabicyclo [4.3.0] undec-7-ene (DBU) or choline.

Compounds of general formula (I) according to Claims 1 to 6, characterized in that

X is hydrogen, Ci-C ₄ alkyl, _{Ci-C4-haloalkyl,} Ci-C ₆ alkoxy, Ci. C ₃ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₃ -haloalkoxy or halogen,

Y _Ci-C4 alkyl, _{Ci-C4-haloalkyl,} Ci-C ₃ _{alkoxy-Ci-C4-alkyl,} _{Ci-C3-haloalkoxy} or halogen,

W is hydrogen, Ci-C ₄ alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, Ci-C ₆ alkoxy, Ci- _{C3-alkoxy-Ci-C4-alkyl,} Ci-Ce-haloalkoxy C ₂ -C 6 -alkenyl, C ₂ -C 6 -alkynyl, halogen or phenyl which is unsubstituted or optionally with one or more substituents independently selected from C ₁ -C ₃ -alkyl, C ₁ -C 4 -haloalkyl, C ₃ -C 6 Cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or halogen may be substituted,

U and V together form a seven-membered ring of the type T'-T ⁴ ,

wherein Z is an oxygen atom, a group -S (O) _n - or a group -IM ^ OR ¹ ) -, n is 0, 1 or 2,

R ¹ Ci-C ₄ alkyl, _{Ci-C4-haloalkyl} or Ci-C ₄ alkanoyl,

R is C 1 -C ₄ -alkyl or C ₁ -C ₃ -alkoxy-C ₁ -C ₄ -alkyl, R ^{3 is} C 1 -C ₄ -alkyl,

R ⁴ is C ₁ -C ₄ -alkyl or phenyl which is unsubstituted or may be optionally substituted by one or more substituents independently selected from halogen or C ₁ -C 4 -alkyl,

R ⁵ and R ⁵ 'is methoxy or ethoxy,

R ⁶ and R ^{7 are} each independently methyl, ethyl or phenyl,

E is an alkali metal ion, an ionic equivalent of an alkaline earth metal, an ionic equivalent of aluminum, an ionic equivalent of a transition metal, a magnesium-halogen cation or an ammonium ion optionally having one, two, three or all four hydrogen atoms represented by identical or different radicals from the groups C1 C5-alkyl, Ci-C6-alkoxy or C3-C7-cycloalkyl, or a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or each represents protonated l, 4-diazabicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] undec-7-ene (DBU) or choline.

8. A herbicidal composition comprising a compound of general formula (I) according to any one of claims 1 to 7 or an agrochemically acceptable salt thereof, and optionally an agrochemically acceptable carrier, diluent and / or solvent.

9. A herbicidal composition according to claim 8, containing at least one further

Pesticide-active substance from the group of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

10. A herbicidal composition according to claim 8 or 9 containing a safener.

11. A herbicidal composition according to any one of claims 8 to 10, containing a further herbicide.

12. A method for controlling undesired plant growth, wherein the compound of general formula (I) according to any one of claims 1 to 7, applied to the plant to be controlled, plant parts, plant seeds or the area on which the unwanted plant growth takes place.

13. The method of claim 12, wherein the undesired plant growth is selected from grassy monocotyledonous weeds.

14. A method according to claims 12 or 13, wherein the plant growth of resistant grasses in crops is controlled, and wherein the herbicidal composition according to claims 1 to 7 is applied to the weed to be controlled.

A method according to claim 14, wherein the crop is selected from wheat, barley, rye, oats, rice, sugar beet, soybean, rapeseed, sunflower and corn.

16. Use of compounds of formula (I) or an agrochemically acceptable salt thereof according to claims 1 to 7 for controlling harmful plants.

17. Use according to claim 16, characterized in that the compound of formula (I) or an agrochemically acceptable salt thereof for controlling harmful plants in crops of crops is used.

Use according to claim 16, characterized in that the useful plants are transgi useful plants.