EP1242387A1

EP1242387A1 - Substituted phenyluracils and their use as herbicides

Info

Publication number: EP1242387A1
Application number: EP00971405A
Authority: EP
Inventors: Roland Andree; Hans-Georg Schwarz; Mark Wilhelm Drewes; Dieter Feucht; Rolf Pontzen; Ingo Wetcholowsky
Original assignee: Bayer AG
Current assignee: Bayer CropScience AG
Priority date: 1999-11-11
Filing date: 2000-10-31
Publication date: 2002-09-25
Also published as: WO2001034575A1; BR0015483A; CO5221066A1; PL354921A1; DE19954312A1; JP2003513960A; CN1390208A; US6815398B1; AU778738B2; AR030919A1; RU2002115661A; CA2390645A1; KR20020059643A; AU1027301A; MXPA02004659A

Abstract

The invention relates to novel substituted phenyluracils of general formula (I), in which: n = 0, 1 or 2; R1 = H, NH2 or optionally substituted alkyl, R2 = carboxy, cyano, carbamoyl, thiocarbamoyl or optionally substituted alkyl or alkoxycarbonyl; X = hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, phenylcarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkinyl, alkinyloxy or alkinyloxycarbonyl. In the case where n > 1, X, in the individual possible compounds, may have multiple given meanings.

Description

SUBSTITUTED PHENY URACI E AND THEIR USE AS HERBICIDES

It relates to new substituted phenyluracils and new intermediates for their preparation and their use as herbicides.

Certain substituted aryluracils are already known from the (patent) literature (cf. EP-A-255047, EP-A-260621, EP-A-408382, EP-A-438209, EP-A-473551, EP-A- 517181, EP-A-563384, WO-A-91/00278, WO-A-91/07393, WO-A-93/14073, WO-A-98/41093, US-A-4979982, US-A- 5084084, US-A-5127935, US-A-5154755, US-A-5169430, US-A-5486610, US-A-5356863). However, these connections have so far not gained any particular importance.

New substituted phenyluracils of the general formula (I)

in which

n stands for the numbers 0, 1 or 2,

R.1 represents hydrogen, amino or optionally substituted alkyl,

R2 represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted alkyl or alkoxycarbonyl,

X for hydroxyl, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino, Alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, phenylcarbonyloxy, alkylcarbonylamino, alkoxy- carbonylamino, alkylsulfonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkynyl, alkynyloxy or alkynyloxycarbonyl is - where in the case that n is greater than 1 , X can also have different meanings in the individual possible compounds,

found.

In the definitions, the hydrocarbon chains, such as alkyl, are also straight-chain or branched, in each case in conjunction with heteroatoms, such as in alkoxy.

If the compounds of the general formula (I) according to the invention contain substituents with asymmetric carbon atoms, the invention relates in each case to the R-enantiomers and the S-enantiomers as well as any mixtures of these enantiomers, in particular the racemates.

n is preferably the number 1 or 2.

Rl preferably represents hydrogen, amino or optionally C1-C4-alkyl substituted by cyano, carboxy, fluorine, chlorine, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxy-carbonyl.

R ^ preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by fluorine-substituted C1-C4-alkyl or C1-C4-alkoxycarbonyl.

X preferably represents hydroxyl, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, each optionally by hydroxyl, cyano, carboxy, carbamoyl, fluorine, chlorine, C1-C4- Alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfmyl, C 1 -C4-alkylsulfonyl, Cj- C4-alkyl-carbonyl, C 1 -C4-alkoxy-carbonyl, C2-C4-alkenyl-oxycarbonyl, C2-C4- Alkynyloxycarbonyl, C1 -C4 alkylaminocarbonyl, di (C1 -C4 alkyl) amino carbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl or alkylamino, each with 1 up to 6 carbon atoms, for dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, for alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy or alkylaminocarbonyloxy each having 1 or each substituted by cyano, fluorine, chlorine, bromine or C 1 -C 4 -alkoxy up to 6 carbon atoms in the alkyl groups, for dialkylaminocarbonyl or dialkylaminocarbonyloxy, each with 1 to 6 carbon atoms in the alkyl groups, for phenylcarbonyloxy, for each alkylcarbonylamino optionally substituted by fluorine, chlorine or bromine, Alkoxycarbonylamino, alkylsulfonylamino, each having up to 6 carbon atoms, or for alkenyl, alkenyloxy, alkenyloxycarbonyl, alkynyl, alkynyloxy or alkynyloxycarbonyl, each optionally substituted by cyano, carboxy, fluorine, chlorine, bromine or C 1 -C 4 -alkoxycarbonyl, each with up to 6 carbon atoms.

n particularly preferably stands for the number 1.

Rl particularly preferably represents hydrogen, amino or methyl.

R2 particularly preferably represents carboxy, cyano, carbamoyl, methoxycarbonyl or trifluoromethyl.

X particularly preferably represents hydroxy, mercapto, amino, nitro, cyano,

Carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, for each optionally by cyano, carboxy, carbamoyl, fluorine, chlorine,

Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propyl thio, methylsulfmyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, allyloxycarbonyl, l-buten-3-yl-oxy-carbonyl, 2- Buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, l-butyn-3-yl-oxy-carbonyl, 2-butyn-4-yl-oxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-

Propylamino-carbonyl, dimethylaminocarbonyl, diethylamino-carbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl or benzyl-aminocarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for dimethylamino or diethylamino, for acetyl, propionyl, n- or i-butyroyl which are each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl,

Ethylaminocarbonyl, n- or i-propylaminocarbonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n- -Butylaminocarbonyloxy, for dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy or diethylaminocarbonyloxy, for n- or i-butylcarbonyloxy, for phenylcarbonyloxy, for each optionally substituted by fluorine or chlorine, acetylamino, propionylamino, n- or i-butyroylylamino, methoxy- carbonyl n- or i-propoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, or for ethenyl optionally substituted by cyano, carboxy, fluorine, chlorine, methoxycarbonyl or ethoxycarbonyl, Propenyl, propenyloxy, propenyloxycarbonyl, ethynyl, propynyl, propynyloxy or propynyloxycarbonyl. very particularly preferably represents hydroxyl, mercapto, amino, in each case by cyano, carboxy, carbamoyl, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl, Ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, allyloxycarbonyl, l-buten-3-yl-oxy-carbonyl , 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butin-3-yl-oxy-carbonyl, 2-butyn-4-yl-oxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i- Propylamino-carbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl or benzylaminocarbonyl substituted methyl, methoxy, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethoxy, n- or i -Propoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, each optionally with cyano, carboxy, carbamoy l, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl , Ethoxycarbonyl, n- or i-propoxy-carbonyl, allyloxycarbonyl, l-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, l-butyn-3-yl-oxy- carbonyl, 2-butyn-4-yl-oxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-

Propylamino-carbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl or benzylaminocarbonyl substituted n-, i-, s- or t-butoxy, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for dimethylamino or diethylamino, for each by cyano,

Fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy substituted methoxycarbonyl or ethoxycarbonyl, for in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy acetyl, propionyl, n- or i-butyroyl , n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, acetyloxy,

Propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyl oxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n- or i-butylaminocarbonyloxy, for dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy or diethylaminocarbonyloxy, for n- or i-butyl carbonyloxy, for phenylcarbonyloxy, for each optionally substituted by fluorine or chlorine, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propyl- sulfonylamino, n-, i-, s- or t-butylsulfonylamino, or if appropriate by cyano, carboxy, fluorine, chlorine, methoxycarbonyl or

Ethoxycarbonyl substituted ethenyl, propenyl, propenyloxy, propenyloxycarbonyl, ethynyl, propynyl, propynyloxy or propynyloxycarbonyl.

most preferably represents in each case cyano, carboxy, carbamoyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, allyloxycarbonyl, l-buten-3-yl-oxy-carbonyl, 2 - buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butin-3-yl-oxy-carbonyl, 2-butyn-4-yl-oxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl, Dimethylaminocarbonyl, Diethylaminocarbonyl, Phenoxycarbonyl, Benzyloxycarbonyl, Phenylaminocarbonyl or

Benzylaminocarbonyl (and optionally additionally substituted by fluorine or chlorine) substituted methyl, ethyl, n-propyl, n-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, for acetyloxy, propionyloxy, n - or i- butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-

Propylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy or phenylcarbonyloxy, for n- or i-butylcarbonyloxy, for dimethylamino, n- or i-butylaminocarbonyloxy, or for ethenyl, propylene, each substituted by cyano, carboxy, methoxycarbonyl or ethoxycarbonyl (and optionally additionally by fluorine or chlorine) , Propenyloxy, ethynyl, propynyl or propynyloxy. According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred.

According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

According to the invention, very particular preference is given to the compounds of the formula (I) in which a combination of those listed above as being particularly preferred

Meanings exist.

Most preferred according to the invention are the compounds of formula (I) in which there is a combination of the meanings listed as most preferred above.

A very particularly preferred group are the compounds of the formula (I)

in which

n represents 1 or 2,

Rl represents hydrogen or methyl,

R ^ stands for trifluoromethyl, carbamoyl, carboxy, methoxycarbonyl or cyano, and X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, allyloxy-carbonyl, propargyloxycarbonyl, l-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, l-butyn-3 -yl-oxy-carbonyl, 2-butyn-4-yl-oxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl, dimethylaminocarbonyl, diethylamino-carbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl or benzyl-aminocarbonyl-substituted methyl, Ethyl, methoxy, ethoxy, methylthio,

Ethylthio, methoxycarbonyl or ethoxycarbonyl, or represents ethenyl substituted by methoxycarbonyl or ethoxycarbonyl or

X for each by cyano, carboxy, carbamoyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,

Allyloxycarbonyl, 1-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butyn-3-yl-oxy-carbonyl, 2-butyn-4-yl-oxy- carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl or benzylaminocarbonyl (and optionally additionally substituted by fluorine or chlorine) methyl, ethyl, n-propyl, n-butyl, Methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, for acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, Ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy or phenylcarbonyloxy, for n- or i-butylcarbonyloxy, for dimethylamino, n- or i-butylaminocarbonyloxy, or for each by cyano, carboxy, methoxycarbonyl or ethoxycarbonyl (and optionally additionally by Fluorine or chlorine) substituted ethenyl, propenyl, propenyloxy, ethynyl, propynyl or propynyloxy. Another very particularly preferred group are those compounds of the formula (I) in which

n represents 1 or 2,

R ^{1 represents} methyl,

R ^ represents trifluoromethyl, carbamoyl, carboxy, cyano or methoxycarbonyl, and

X has one of the meanings given above for compounds of the formula (I).

Another very particularly preferred group are those compounds of the

Formula (I) in which

n represents 1 or 2,

R ^{1 represents} hydrogen,

R represents trifluoromethyl, carbamoyl, carboxy, cyano or methoxycarbonyl, and

X has one of the meanings given above for compounds of the formula (I).

Another very particularly preferred group are those compounds of the formula (I) in which

represents 1 or 2, R ^{1 represents} hydrogen or methyl,

R ^{2 represents} trifluoromethyl, and

X has one of the meanings given above for compounds of the formula (I).

Another very particularly preferred group are those compounds of the formula (IA)

in which

R ^{1 represents} hydrogen or methyl,

R ^{2 represents} trifluoromethyl, and

X for carboxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl or for methyl, ethyl, methoxy, ethoxy substituted by phenylaminocarbonyl or

X for n- or i-butylaminocarbonyloxy, n- or i-butylcarbonyloxy, dimethylamino, methoxycarbonyloxy, ethoxycarbonyloxy, methylamino carbonyloxy, ethylaminocarbonyloxy, or represents dimethylaminocarbonyloxy.

Another very particularly preferred group are those compounds of the formula (IA) in which

R ^{1 represents} hydrogen or methyl,

R ^{2 represents} trifluoromethyl, and

X represents methyl, methoxy or ethoxy substituted by carboxy, methoxycarbonyl or ethoxycarbonyl, or

X represents methoxycarbonyloxy, ethoxycarbonyloxy, methylaminocarbonyloxy or ethylaminocarbonyloxy.

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.

Examples of the compounds of the general formula (I) according to the invention are listed in the groups below.

Group 1

X ¹ has the meanings given in the list below:

4- (1-carboxy) ethoxy, 4- (1-ethoxycarbonyl) ethoxy, 3 - (1-ethoxycarbonyl) ethoxy,

3-ethoxycarbonylmethoxy, 2- (1-ethoxycarbonyl) ethoxy.

Group 2

X ¹ stands for dimethylaminocarbonyl methoxy or methylaminocarbonyl methoxy and

X ² stands for methyl.

Group 3

X ¹ stands for phenylaminocarbonylethoxy or phenylaminocarbonyl methoxy.

Group 4

X ¹ stands for n- or i-butylcarbonyloxy or ethoxycarbonyloxy. Group 5

X ¹ stands for 4-ethylaminocarbonyloxy, 4- (n- or i-) butylaminocarbonyloxy, 3-methylaminocarbonyloxy or 2-methylaminocarbonyloxy.

Group 6

X ¹ stands for dimethylamino and

R ^! stands for hydrogen or methyl.

Group 7

X ¹ stands for 2-chlorine, 3-chlorine, 4-chlorine, 3-fluorine, 4-fluorine, 3-methyl, 3-cyano, 4-cyano, 2-methylthio, 2-methylsulfmyl or 4-methylsulfmyl. Group 8

X ¹ stands for 2-chlorine, 3-chlorine, 4-chlorine, 2-fluorine, 4-fluorine, 3-methyl, 3-nitro, 4-methyl, 3-cyano, 4-cyano, 2-methylthio, 4 -Nitro, 2-cyano, 4-methylthio or 2-methoxy.

Group 9

4ι stands for (3,4-) Cl ₂ or (2,4-) F ₂ .

Group 10

X _n stands for (3,4-) Cl ₂ or (2,4-) F ₂ . Group 11

X ¹ stands for hydroxy or methoxy, and

X ² stands for methyl.

Group 12

X ¹ stands for 4-methoxy, 3-chlorine or 4-cyano.

Group 13

X ¹ stands for 3-trifluoromethyl, 4-chloro, 3-methoxy, 3-chloro or 4-cyano. Group 14

X ¹ stands for 3-methoxy, 3-chlorine or 4-cyano.

Group 15

X ¹ stands for 3-trifluoromethyl, 4-chloro, 3-methoxy, 3-chloro or 4-cyano.

Group 16

R ² stands for methoxycarbonyl, carbamoyl or cyano.

Group 17

R ² stands for carbamoyl or cyano. The new substituted phenyluracils of the general formula (I) have interesting biological properties. They are particularly characterized by their strong herbicidal activity.

The new substituted phenyluracils of the general formula (I) are obtained if

(a) Halogenophenyluracils of the general formula (II)

in which

R and R ^ have the meaning given above and

X ^ represents halogen,

with aryl compounds of the general formula (III)

in which

n and X have the meaning given above,

- or with metal salts of compounds of the general formula (III) -

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or if you

(b) aminoalkenates of the general formula (IV)

in which

R2 has the meaning given above and

R represents alkyl, aryl or arylalkyl,

with aryl isocyanates of the general formula (V)

in which

n and X have the meaning given above,

or with aryl urethanes (aryl carbamates) of the general formula (VI)

in which

n and X have the meaning given above and

R represents alkyl, aryl or arylalkyl, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or if you

(c) N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII)

in which

n and X have the meaning given above and

R 'represents alkyl,

reacted with a metal hydroxide in the presence of water and optionally in the presence of an organic solvent,

or if you

(d) substituted phenyluracils of the general formula (Ia) in which

n and X have the meaning given above,

with l-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (VIII)

X4-A1 (VIII)

in which

A represents optionally substituted alkyl and

X ^ represents halogen or the grouping -O-SO2-O-A,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

and, if appropriate, subsequently carries out electrophilic or nucleophilic or oxidation or reduction reactions as part of the substituent definition.

The compounds of the general formula (I) can be converted by conventional methods into other compounds of the general formula (I) as defined above, for example by esterification or hydrolysis (for example X: OCH ₂ COOH → OCH2COOC2H5, OCH (CH ₃ ) COOCH ₃ → OCH (CH ₃ ) COOH), Conversion of carboxy compounds into other carboxylic acid derivatives using conventional methods (for example R ² : COOH → CN, CN → CSNH ₂ , COOH → COOCH ₃ , COOCH ₃ → CONH ₂ ); see. the manufacturing examples).

If, for example, 1- (4-cyano-2,5-difluorophenyl) -4-chlorodifluoromethyl-3, 6-dihydro-2,6-dioxo-1 (2H) -pyrimidine and 1- (4-hydroxy) are used -phenoxy) - ethyl propionate as starting materials, the course of the reaction in process (a) according to the invention can be outlined using the following formula:

If, for example, 3-amino-4,4,4-trifluoro-crotonic acid methyl ester and 4-

Cyano-2-fluoro-5-phenoxy-phenyl isocyanate as starting materials, the course of the reaction in process (b) according to the invention can be outlined by the following formula:

If, for example, [1- (4-cyano-2-fluoro-5-phenoxy-phenyl) -2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl] carbamate is used as the starting material, then the course of the reaction in the process according to the invention can be sketched using the following formula:

If, for example, l- [2-fluoro-4-cyano-5- (4-methoxycarbonylmethoxyphenoxy) phenyl] -4-difluoromethyl-3,6-dihydro-2,6-dioxo-1 (2H) -pyrimidine and

Methyl bromide as starting materials, the course of the reaction in process (d) according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the halophenyluracils to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I). In formula (II), R and R have in particular ^ those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for R and R ^; X ^ preferably represents fluorine or chlorine, especially fluorine.

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. EP-A-648749).

Formula (III) provides a general definition of the aryl compounds to be used further as starting materials in process (a) according to the invention. In the

Formula (III) n and X have in particular those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for n and X.

The starting materials of the general formula (III) are known organic synthetic chemicals.

Formula (IV) provides a general definition of the aminoalkenic acid esters to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I). In the general formula (IV), R has in particular the meaning which has already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for R ² ; R preferably represents -C ₄ alkyl, phenyl or benzyl, in particular methyl or ethyl.

The starting materials of the general formula (IV) are known and / or can be prepared by processes known per se (cf. J. Heterocycl. Chem. 9 (1972), 513-522). Formula (V) provides a general definition of the aryl isocyanates to be used further as starting materials in process (b) according to the invention. In the general formula (V), n and X have in particular those meanings which have already been given above as preferred, particularly preferred or very particularly preferred for n and X in connection with the description of the compounds of the general formula (I) according to the invention.

The new aryl isocyanates of the general formula (V) are obtained if aniline derivatives of the general formula (IX)

in which

nand X have the meaning given above,

with phosgene in the presence of a diluent, e.g. Chlorobenzene, at temperatures between -20 ° C and + 150 ° C (see e.g. also EP-A-648749).

Formula (VI) provides a general definition of the aryl urethanes to be used as starting materials in process (b) according to the invention. In the general formula (VI), n and X have in particular those meanings which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for n and X; R preferably stands for

Cι-C ₄ - alkyl, phenyl or benzyl, especially for methyl or ethyl.

The new aryl urethanes of the general formula (VI) are obtained if aniline derivatives of the general formula (FX) in which

n and X have the meaning given above,

with chlorocarbonyl compounds of the general formula (X)

RO-CO-Cl (X)

in which

R has the meaning given above,

optionally in the presence of an acid acceptor, e.g. Pyridine, and optionally in the presence of a diluent, e.g. Methylene chloride, at temperatures between -20 ° C and + 100 ° C (see. The manufacturing examples).

The aniline derivatives of the general formula (IX) required as precursors are not yet known.

The aniline derivatives of the general formula (IX) are obtained.

in which

n and X have the meaning given above, if anilines of the general formula (XI)

in which

X has the meaning given above,

with phenols of the general formula (III)

in which

n and X have the meaning given above,

- or with metal salts of compounds of the general formula (III) -

optionally in the presence of a reaction auxiliary, e.g. Sodium hydride, and optionally in the presence of a diluent, e.g. N-methylpyrrolidone, at temperatures between 0 ° C and 150 ° C (see. The preparation examples).

Formula (VII) provides a general definition of the N-aryl-1-alkoxycarbonylamino-maleimides to be used as starting materials in process (c) according to the invention for the preparation of compounds of the general formula (I). In the general formula (VII), n and X have in particular those meanings which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for n and X; R 'preferably represents C 1 -C ₄ -alkyl, in particular methyl or ethyl. The N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII) are obtained if (2,5-dioxo-2,5-dihydro-furan-3-yl) -carbamic acid alkyl ester of the general formula (XII)

in which

R 'represents alkyl (in particular methyl or ethyl),

with aniline derivatives of the general formula (IX)

in which

nand X have the meaning given above,

optionally in the presence of a diluent, e.g. Acetic acid, at temperatures between 0 ° C and 200 ° C, preferably between 50 ° C and 150 ° C.

The precursors of the general formula (XII) are known and / or can be prepared by processes known per se (cf. DE 19604229).

The substituted phenyluracils to be used as starting materials in process (d) according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (la). In the formula (Ia), n and X have in particular those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for n and X.

The starting materials of the general formula (Ia) for process (d) can be prepared by processes (a), (b) and (c) according to the invention.

Formula (VIII) provides a general definition of the alkylating agents which are further to be used as starting materials in process (d) according to the invention. In the

Formula (VIII) is preferably A for alkyl with 1 to 4 carbon atoms optionally substituted by cyano, halogen or C1-C4-alkoxy and X ^ for chlorine, bromine, iodine, methylsulfonyloxy or ethylsulfonyloxy; in particular, A represents methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy and X ^ represents chlorine, bromine, iodine, methylsulfonyloxy or ethylsulfonyloxy.

The starting materials of formula (VIII) are known organic synthetic chemicals.

The processes according to the invention for the preparation of the compounds of the general formula (I) are preferably carried out using diluents. Suitable diluents for carrying out processes (a), (b), (c) and (d) in addition to water are, in particular, inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-di methylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

Suitable reaction auxiliaries for processes (a), (b), (c) and (d) according to the invention are generally the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide,

Sodium or potassium methoxide, ethanolate, u or i-propanolate, n, i, s or t butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-di-isopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N- Dimethyl-benzylamine, pyridine, 2-methyl, 3-

Methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino -pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0] -undec-7-ene (DBU).

Phase transfer catalysts are also suitable as further reaction aids for the processes according to the invention. Examples of such catalysts are:

Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, Hexadecyl-trimethylammonium chloride, hexadecyl-trimethylammonium bromide, benzyl-trimethylammonium chloride, benzyl-triethylammonium chloride, benzyl-trimethylammonium hydroxide, benzyl-triethylammonium hydroxide, benzyl-tributylammonium chloride, benzyl-tribon bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributylhexadecylphosphonium bromide,

Butyl triphenylphosphonium chloride, ethyl trioctylphosphonium bromide, tetraphenylphosphonium bromide.

The reaction temperatures can be varied within a substantial range when carrying out processes (a), (b), (c) and (d). In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

The processes according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out the processes according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. The work-up is carried out using customary methods (cf. the manufacturing examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow in places grow where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,

Ranunculus, Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasumirumum, Scalumumum, Scalumumum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus,

Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.

Depending on the concentration, the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, for example forests, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, can be used on ornamental and sports turf and pastures and for selective weed control in annual crops.

The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. also organic

Solvents are used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable

Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,

Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite waste liquor and

Methylcellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known herbicides for weed control, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example

Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl) Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole,

Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidone (-ethyl), Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-proazpargg) Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (- methyl), Cumyluron, Cyanazines, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2, 4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Difluefenzopyr, Dimefüron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflat, Dinitramine, Dipitamin Dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethofumesate,

Ethoxyfen, Ethoxysulfüron, Etobenzanid, Fenoxaprop (-P-ethyl), Flamprop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Fluazifop (-P-butyl), Fluazolate, Flucarbazone, Flufenacet, flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium),

Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluothiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (- isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl) , Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfüron, Iodosulfuron, Ioxynil, Isopropalin, Isoproturon, Isouronoxoxloxifoxole . Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolechlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl) Molurin, -methyl- Monurol, -methyl-Molurin, Naproanilide, Napropamide, Neburon, Nicosulfüron, Norflurazon, Orben-carb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen,

Paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron (-methyl), prometryn, propachlor, propanil, propaquiza- fop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufenolate (-ethyl) ), Pyrazoxyfen, pyribenzoxime, pyributicarb, pyridates, pyriminobac (methyl), pyrithiobac (sodium), quinchlorac, quinmerac,

Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefüryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthoxylazone, Teprutoxyl Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (- methyl), Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfüron, Triben- uιon (-methyl), Triclopyr, Tridiphane, Trifluraluron and Triflusuron.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying,

Spray, sprinkle.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing. The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

Preparation Examples:

example 1

(Method (a))

2.5 g (10 mmol) of 4-methoxyphenol are placed in 50 ml of dimethyl sulfoxide and mixed with 1.6 g of sodium hydride (60%). The mixture is stirred for 30 minutes at room temperature (approx. 20 ° C). Then 3.2 g (10 mmol) of 4- (3,6-dihydro-2,6-dioxo-4-trifluoromethyl-l (2H) -pyrimidin-l-yl) -2,5-difluoro-benzonitrile are added ,

The reaction mixture is stirred at 60 ° C. for 18 hours and then poured into approximately the same volume of IN hydrochloric acid. The crystalline product is isolated by suction, stirred with a mixture of 30 ml of ethyl acetate and 300 ml of diethyl ether and sucked dry. The organic mother liquor is concentrated in a water jet vacuum and the residue is worked up by column chromatography (silica gel, chloroform / ethyl acetate, vol .: 2: 1). The first fraction obtained in this way is concentrated in a water jet vacuum, the residue is dissolved in boiling methylene chloride, after cooling the supernatant solvent is decanted, the residue is stirred with diethyl ether / diisopropyl ether and the crystalline product is isolated by suction.

0.90 g (21% of theory) of 4- (3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidin-1-yl) -5-fluoro-2- ( 4-methoxy-phenoxy) -benzonitrile with a melting point of 84 ° C. Example 2

(Method (b))

A mixture of 0.50 g (1.2 mmol) of 4- (3,6-dihydro-2,6-dioxo-4-trifluoromethyl)

1 (2H) pyrimidine-1-yl) -5-fluoro-2- (4-methoxyphenoxy) benzonitrile, 0.20 g

(1.8 mmol) dimethyl sulfate, 0.30 g (2.4 mmol) potassium carbonate and 100 ml acetone are heated under reflux for 15 hours and then concentrated in a water jet vacuum. The residue is shaken with 50 ml of IN hydrochloric acid / 50 ml of ethyl acetate, the organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, dissolved in ethyl acetate, washed with 5% aqueous disodium hydrogenphosphate solution, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is stirred with petroleum ether and the solvent is carefully distilled off in a water jet vacuum.

0.3 g (57% of theory) of 4- (3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidin-1-yl) -5 are obtained -fluoro-2- (4-methoxy-phenoxy) -benzonitrile from

Melting point 62 ° C.

Analogously to preparation examples 1 and 2 and in accordance with the general description of the preparation processes according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in table 1 below.

The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase inversion column (C 18). Temperature: 43 ° C.

(a) Eluents for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^a ). (b) eluents for determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^D ).

The calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).

The lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.

Starting materials of formula (VI):

Example (VI- 1)

2.8 g (11 mmol) l-amino-4-cyano-2-fluoro-5- (4-methoxy-phenoxy) -benzene are placed in 100 ml methylene chloride with 1.7 g pyridine and at room temperature (approx.

20 ° C) with 1.25 g (12 mmol) of ethyl chloroformate. The mixture is stirred at room temperature for 2 hours and then shaken with IN hydrochloric acid. The organic phase is concentrated in a water jet vacuum, the residue is crystallized with diethyl ether / diisopropyl ether and the solid product is isolated by suction.

1.2 g (34% of theory) of N- (4-cyano-2-fluoro-5- (4-methoxyphenoxy) phenyl) O-ethyl carbamate are obtained. 1H NMR (D6-DMSO, δ): 7.85 u. 7.89 ppm.

Starting materials of formula (IX):

Example (IX- 1)

1.3 g (10 mmol) of 4-methoxy-phenol in 100 ml of N-methyl-pyrrolidone are mixed at room temperature with 0.50 g of sodium hydride (60%) and after briefly stirring with 1.5 g of 4-cyano-2, 5-difluoro-aniline added. The reaction mixture is then stirred at 100 ° C. for 20 hours. After cooling, it is diluted with water and then with 1N hydrochloric acid and, after stirring for two hours, the solid product is isolated by suction and dried on clay.

1.9 g (73% of theory) of l-amino-4-cyano-2-fluoro-5- (4-methoxyphenoxy) benzene with a melting point of 135 ° C. are obtained.

Analogously to Example (IX-1), for example the compounds of the general formula (IX) listed in Table 2 below can also be prepared.

Table 2: Examples of the compounds of the formula (IX)

Application examples:

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After approximately 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The concentration of the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means: 0% = no effect (like untreated control)

100%. = total annihilation

In this test, for example, the compounds according to Preparation Examples 4 and 6 show a strong action against weeds. Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

Test plants with a height of 5 - 15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.

It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to Preparation Examples 4 and 6 show a strong action against weeds.

Claims

claims

1. Substituted phenyluracils of the general formula (I)

in which

n stands for the numbers 0, 1 or 2,

R represents hydrogen, amino or optionally substituted alkyl,

X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylylaminoxycarbonyl, alkoxycarbonyloxycarbonyl, carbonyl - oxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, phenylcarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkynyl, alkynyloxy or alkynyloxycarbonyl - where, in the case that n is greater than 1, X in the individual possible compounds is also different from the given possible compounds Can have meanings. Substituted phenyluracile according to claim 1, characterized in that

n represents the numbers 1 or 2,

R represents hydrogen, amino or optionally by cyano, carboxy,

Fluorine, chlorine, C 4 -C 4 -alkoxy or C 4 -C 4 alkoxy-carbonyl-substituted C 1 -C 4 -alkyl,

R2 for carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by fluorine-substituted C1-C4-alkyl or C1-C4-

Alkoxy-carbonyl stands, and

X for hydroxyl, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, for each optionally by hydroxy, cyano, carboxy, carbamoyl, fluorine, chlorine, C1-C4-

Alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfmyl, C1-C4-alkylsulfonyl, Cι-C4-alkyl-carbonyl, Cι-C4-alkoxy-carbonyl, C2-C4-alkenyl-oxycarbonyl, C2-C4-alkynyl- oxycarbonyl, -C -C4-alkylamino-carbonyl, di- (Cj -C4-alkyl) -amino-carbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl substituted alkyl,

Alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl or alkylamino each having 1 to 6 carbon atoms, for dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, for alkylcarbonyl, alkoxycarbonyl optionally substituted by cyano, fluorine, chlorine, bromine or C1-C4-alkoxy, Alkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy or alkylaminocarbonyloxy each having 1 to 6 carbon atoms in the alkyl groups, for dialkylaminocarbonyl or dialkylaminocarbonyloxy each having 1 to 6 carbon atoms in the alkyl groups, for phenylcarbonyloxy, for alkylcarbonylamino, alkoxycarbonylylamino, alkoxyulfonylamino, optionally substituted by fluorine, chlorine or bromine or for in each case optionally substituted by cyano, carboxy, fluorine, chlorine, bromine or -CC4-alkoxycarbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkynyl, alkynyloxy or alkynyloxycarbonyl each having up to 6 carbon atoms.

3. Substituted phenyluracile according to claim 1 or 2, characterized in that

n stands for the number 1,

R represents hydrogen, amino or methyl,

R2 represents carboxy, cyano, carbamoyl, methoxycarbonyl or trifluoromethyl, and

X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, for each optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy , Methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl,

Acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, allyloxycarbonyl, l-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, Propargyloxycarbonyl, 1-butin-3-yl-oxy-carbonyl, 2-butyn-4-yl-oxy-carbonyl, methylamino-carbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl, dimethylaminocarbonyl, diethylamino-carbonyl, phenoxycarbonyl, benzyloxycarbonyl , Phenylaminocarbonyl or benzylaminocarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t -Butoxy, methyl-thio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl,

Methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i- Propylamino, n-, i-, s- or t-butylamino, for dimethylamino or diethylamino, for acetyl, propionyl, n- or i-, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy Butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonylyloxy, methylaminocyloxy, methylaminocyloxy n- or i-Propylaminocarbonyloxy, n- or i-butylaminocarbonyloxy for dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminocarbonyloxy or diethylaminocarbonyloxy, for n- or i-butylcarbonyloxy, for phenylcarbonyloxy, for acetylamino, optionally substituted by fluorine or chlorine, n-propion - or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulfonylamino, ethyl - sulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, or for ethenyl, propenyl, propenyloxy, propenyloxycarbonyl, ethynyl, propynyl, propynyloxy or propynyloxycarbonyl, each optionally substituted by cyano, carboxy, fluorine, chlorine, methoxycarbonyl or ethoxycarbonyl stands.

4. Substituted phenyluracile according to any one of claims 1 to 3, characterized in that

X preferably for hydroxy, mercapto, amino, for each by cyano,

Carboxy, carbamoyl, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl , n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, allyloxycarbonyl, 1-butene

3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butyn-3-yl-oxy-carbonyl, 2-butyn-4-yl-oxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl or benzylaminocarbonyl , Methoxy, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, each optionally by Cyano, carboxy, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfmyl, ethylsulfinyl, methylsulfonyl,

Ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, allyloxycarbonyl, l-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy- carbonyl, propargyloxycarbonyl, 1-butin-3-yl-oxy-carbonyl, 2-butyn-4-yl-oxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-

Propylamino-carbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl or benzylaminocarbonyl substituted n-, i-, s- or t-butoxy, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for dimethylamino or diethylamino, for each methoxycarbonyl or ethoxycarbonyl substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, for each optionally by cyano, fluorine, chlorine, methoxy , Ethoxy, n- or i-propoxy substituted acetyl, propionyl, n- or i-butyroyl, n- or i-propoxycarbonyl, methylaminocarbonyl,

Ethylaminocarbonyl, n- or i-propylaminocarbonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n- or i-butyl , Diethylaminocarbonyl, dimethylaminocarbonyloxy or diethylaminocarb- onyloxy, for n- or i-butylcarbonyloxy, for phenylcarbonyloxy, for acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulfonylamino, ethylsulfonylam, each optionally substituted by fluorine or chlorine , n- or i-Propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, or for ethenyl, propenyl, propenyloxy, propenyloxycarbonyl, ethinyl, which are each optionally substituted by cyano, carboxy, fluorine, chlorine, methoxycarbonyl or ethoxycarbonyl, Propynyl, propynyloxy or propynyloxycarbonyl is available.

5. Substituted phenyluracile according to any one of claims 1 to 4, characterized in that

X most preferably stands for cyano, carboxy,

Carbamoyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, allyloxycarbonyl, 1-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, Propargyloxycarbonyl, l-butyn-3-yl-oxy-carbonyl, 2-butyn-4-yl-oxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl (phenylaminocarbonyl or methyl, ethyl, n-propyl, n-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, optionally substituted by fluorine or chlorine), for acetyloxy,

Propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy or phenylcarbonyloxy but for n- or i-carbonyloxy, for n- or i-carbonyloxy, for n- or i-cyclooxy, Dimethylamino, n- or i-butylaminocarbonyloxy, or for each by cyano, carbo- oxy, methoxycarbonyl or ethoxycarbonyl (and optionally additionally substituted by fluorine or chlorine) ethenyl, propenyl, propenyloxy, ethynyl, propynyl or propynyloxy.

Compounds of formula (I) according to claim 1, characterized in that

n represents 1 or 2,

R represents hydrogen or methyl,

R2 represents trifluoromethyl, carbamoyl, carboxy, methoxycarbonyl or cyano, and

X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl,

Thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, allyloxycarbonyl, propargyloxycarbonyl , 1-butene-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl,

1-butin-3-yl-oxy-carbonyl, 2-butin-4-yl-oxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl, dimethylaminocarbonyl, diethylamino-carbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl or benzylaminocarbonyl substituted methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio,

Methoxycarbonyl or ethoxycarbonyl, or represents ethenyl substituted by methoxycarbonyl or ethoxycarbonyl, or

X for each by cyano, carboxy, carbamoyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxycarbonyl, allyloxycarbonyl, l-buten-3-yl-oxy-carbonyl, 2- Buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butin-3-yl-oxy-carbonyl, 2-butyn-4-yl-oxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl, dimethylaminocarbonyl , Diethylaminocarbonyl, phenoxycarbonyl, benzyloxycarbonyl, phenylaminocarbonyl or benzylaminocarbonyl (and optionally additionally substituted by fluorine or chlorine) substituted methyl, ethyl, n-propyl, n-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, for acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy, phenylaminocarbonyloxy, phenylaminocarbonyloxy, or or i-butylcarbonyloxy, for dimethylamino, n- or i-butylaminocarbonyloxy, or for each by cyano, carboxy, methoxycarbonyl or ethoxycarbonyl (and optionally additionally by fluorine or

Chlorine) substituted ethenyl, propenyl, propenyloxy, ethynyl, propynyl or propynyloxy.

7. Compounds of formula (I) according to claim 1, characterized in that

n represents 1 or 2,

R ^{1 represents} methyl,

R2 represents trifluoromethyl, carbamoyl, carboxy, cyano or methoxycarbonyl.

8. Compounds of formula (I) according to claim 1, characterized in that n represents 1 or 2,

R ^{1 represents} hydrogen, and

R ^{2 represents} trifluoromethyl, carbamoyl, carboxy, cyano or methoxycarbonyl.

9. Compounds of formula (I) according to claim 1, characterized in that

n represents 1 or 2,

R ^{1 represents} hydrogen or methyl, and

R ^{2 represents} trifluoromethyl.

10. Compounds of the formula (IA),

in which

R ^{1 represents} hydrogen or methyl,

R ^{2 represents} trifluoromethyl, and

X for by carboxy, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dime thylaminocarbonyl, diethylaminocarbonyl or for substituted by phenylaminocarbonyl methyl, ethyl, methoxy, ethoxy, or

X stands for n- or i-butylaminocarbonyloxy, n- or i-butylcarbonyloxy, dimethylamino, methoxycarbonyloxy, ethoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, or for dimethylaminocarbonyloxy.

11. Compounds of formula (IA) according to claim 10, characterized in that

R ^{1 represents} hydrogen or methyl,

R ^{2 represents} trifluoromethyl, and

12. Compounds of the formula (IB),

in which X ¹ for 4- (l-carboxy) ethoxy, 4- (l-ethoxycarbonyl) ethoxy, 3- (l-ethoxycarbonyl) ethoxy, 3-ethoxycarbonylmethoxy or 2- (l-ethoxycarbonyl) ethoxy stands.

13. Compounds of formula (IB) according to claim 12, characterized in that

X ^{1 represents} 4-ethylaminocarbonyloxy, 4- (n- or i-) butylaminocarbonyloxy, 3-methylaminocarbonyloxy or 2-methylaminocarbonyloxy.

14. Compounds of formula (IB) according to claim 12, characterized in that

X ^{1 represents} 2-chlorine, 3-chlorine, 4-chlorine, 3-fluorine, 4-fluorine, 3-methyl, 3-cyano, 4-cyano, 2-methylthio, 2-methylsulfinyl or 4-methylsulfinyl.

15. Compounds of the formula (IC)

in which

X ¹ for dimethylaminocarbonyl methoxy or methylaminocarbonyl methoxy and

X ^{2 represents} methyl.

16. Compounds of formula (IC) according to claim 15, characterized in that

X ¹ for hydroxy or methoxy, and

X ^{2 represents} methyl.

17. Compounds of the formula (ID)

in which

X ^{1 represents} phenylaminocarbonylethoxy or phenylaminocarbonylmethoxy.

18. Compounds of formula (ID) according to claim 17, characterized in that

X ^{1 represents} n- or i-butylcarbonyloxy or ethoxycarbonyloxy.

19. Compounds of the formula (IE)

in which

X ¹ for dimethylamino and

R ^{1 represents} hydrogen or methyl.

20. Compounds of the formula (IF)

in which

X ¹ for 2-chlorine, 3-chlorine, 4-chlorine, 2-fluorine, 4-fluorine, 3-methyl, 3-nitro, 4-methyl, 3-cyano, 4-cyano, 2-methylthio, 4-nitro , 2-cyano, 4-methylthio or 2-methoxy.

21. Compounds of the formula (IG)

in which

X _{n stands} for (3, 4-) Cl ₂ or (2,4-) F ₂ .

22. Compounds of the formula (IH)

in which

X _{n represents} (3,4-) Cl ₂ or (2,4-) F ₂ .

23. Compounds of the formula (IJ)

in which

X ^{1 represents} 4-methoxy, 3-chlorine or 4-cyano.

24. Compounds of the formula (IK)

in which

X ^{1 represents} 3-trifluoromethyl, 4-chloro, 3-methoxy, 3-chloro or 4-cyano.

25. Compounds of the formula (IL)

in which

X ^{1 represents} 3-methoxy, 3-chlorine or 4-cyano.

26. Compounds of the formula (IM)

in which

X ^{1 represents} 3-trifluoromethyl, 4-chloro, 3-methoxy, 3-chloro or 4-cyano.

27. Compounds of the formula (IN)

in which

R ^{2 represents} methoxycarbonyl, carbamoyl or cyano.

28. Compounds of the formula (IO)

in which

R ^{2 represents} carbamoyl or cyano.

29. Compounds of formula (IX)

in which

n and X have the meaning given above.

30. Herbicidal agents, characterized by the content of at least one compound according to one of claims 1 to 28 and conventional extenders.

31. Use of at least one compound according to any one of claims 1 to 28 for controlling unwanted plants.