DE19853864A1 - Substituted phenyluracile - Google Patents

Abstract

The invention relates to novel substituted phenyl uracils of general formula (I) wherein n, Q, R<1>, R<2>, R<3>, R<4>, R<5> and X have the meanings given in the description, to methods and novel intermediate products for producing said substituted phenyl uracils and to their use as herbicides.

Description

The invention relates to new substituted phenyluracils, processes and new ones Intermediates for their manufacture and their use as herbicides.

Certain substituted aryluracils are already known from the (patent) literature (see 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, 2, 3, 4 or 5,
Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH or N (alkyl),
R ^{1 represents} hydrogen, amino or optionally substituted alkyl,
R ^{2 represents} carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted alkyl or alkoxycarbonyl,
R ^{3 represents} hydrogen, halogen or optionally substituted alkyl,
R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,
R ^{5 represents} cyano, carbamoyl, thiocarbamoyl, halogen or in each case optionally substituted alkyl or alkoxy, and
X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyl Alkoxycarbonylamino, alkylsulfonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkynyl, alkynyloxy or alkynyloxycarbonyl - where, if n is greater than 1, X in the individual possible compounds can also have different of the meanings given,
found.

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

As far as the compounds of general formula (I) Substi Containing tuenten with asymmetric carbon atoms relates to the invention each of the R enantiomers and the S enantiomers and any mixtures of these enantiomers, especially the racemates.

The invention preferably relates to substituted phenyluracils of the formula (I) in which
n stands for the numbers 0, 1, 2, 3 or 4,
Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH or N (C ₁ -C ₄ alkyl),
R ¹ represents hydrogen, amino or optionally cyano-, carboxyl-, fluorine-, chlorine-, C ₁ -C ₄ alkoxy or C ₁ -C ₄ -alkoxy-carbonyl-substituted C ₁ -C ₄ - alkyl,
R ^{2 represents} carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by cyano, fluorine, chlorine or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy-carbonyl,
R ^{3 represents} hydrogen, fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl optionally substituted by fluorine or chlorine,
R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine,
R ^{5 represents} cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or in each case optionally substituted by fluorine and / or chlorine, substituted by C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, and
X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, fluorine, chlorine, bromine, iodine, for each optionally by hydroxy, cyano, carboxy, carbamoyl, fluorine, chlorine, C ₁ -C ₄ alkoxy , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ alkyl carbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₂ -C ₄ - Alkenyl-oxycarbonyl, C ₂ -C ₄ -alkynyloxycarbonyl, C ₁ -C ₄ -alkylamino-carbonyl, di- (C ₁ -C ₄ -alkyl) -amino carbonyl or benzyloxycarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkylamino each having 1 to 6 carbon atoms, for dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, for each alkylcarbonyl, alkoxycarbonyl or alkylaminocarbonyl optionally substituted by cyano, fluorine, chlorine, bromine or C ₁ -C ₄ alkoxy up to 6 carbon atoms in the alkyl groups, for dialkylaminocarbonyl with 1 to 6 carbon atoms in the alkyl groups, for each given all alkyl fluorylamino, alkoxycarbonylamino, alkylsulfonylamino substituted by fluorine, chlorine or bromine, or for alkenyl, alkenyloxy, alkenyl oxycarbonyl, alkynyl, alkynyloxy, each optionally substituted by cyano, carboxy, fluorine, chlorine, bromine or C ₁ -C ₄ alkoxycarbonyl or alkynyloxycarbonyl each having up to 6 carbon atoms.

The invention relates in particular to compounds of the formula (I) in which
n represents the numbers 1, 2 or 3,
Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH or N (CH ₃ ),
R ^{1 represents} hydrogen, amino or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
R ^{2 represents} carboxy, cyano, carbamoyl, thiocarbamoyl or in each case methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
R ^{3 represents} hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl or trifluoromethyl, and
X for hydroxyl, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, fluorine, chlorine, bromine, for each optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, allyloxy carbonyl, 1-butene 3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyl oxycarbonyl, 1-butyn-3-yl-oxy-carbonyl, 2-butyn-4-yl-oxy-carbonyl, methyl aminocarbonyl, Ethylaminocarbonyl, n- or i-propylamino-carbonyl, dimethylaminocarbonyl, diethylamino-carbonyl, phenoxycarbonyl, benzyloxy carbonyl, 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, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, Ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butyl amino, for dimethylamino or diethylamino, each optionally with cyano, fluorine, chlorine, methoxy, ethoxy, n- or i -Propoxy-substituted acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, for dimethylaminocarbonyl or diethylamino carbonyl, each optionally substituted by fluorine or chlorine Acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonyl amino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methyl sulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino each optionally substituted by cyano, carboxy, fluorine, chlorine, methoxycarbonyl or ethoxycarbonyl, ethenyl, propenyl, propenyloxy, propenyloxycarbonyl, ethynyl, propynyl, propynyloxy or propynyloxycarbonyl stands.

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

in which
R ^{1 represents} hydrogen, amino or methyl,
R ^{2 represents} trifluoromethyl, chlorodifluoromethyl, difluoromethyl or pentafluoroethyl,
R ^{3 represents} hydrogen, chlorine or methyl,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} cyano or thiocarbamoyl, and
X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, 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, 1-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butyn-3 -yl-oxy-carbonyl, 2-Bu tin-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 methoxy carbonyl or ethoxycarbonyl.

Another very particularly preferred group are those compounds of the formula (IA) in which
R ^{1 represents} methyl,
R ^{2 represents} trifluoromethyl, chlorodifluoromethyl, difluoromethyl or pentafluoroethyl,
R ^{3 represents} hydrogen, chlorine or methyl,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} fluorine, chlorine, bromine or trifluoromethyl, and
X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, 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, 1-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butyn-3 -yl-oxy-carbonyl, 2-Bu tin-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 methoxy carbonyl or ethoxycarbonyl.

Another very particularly preferred group are those compounds of the formula (IA) in which
R ^{1 represents} hydrogen, amino or methyl,
R ^{2 represents} carboxy, cyano, carbamoyl, thicarbamoyl, methoxycarbonyl or ethoxycarbonyl,
R ^{3 represents} hydrogen, chlorine or methyl,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} cyano, thiocarbamoyl, fluorine, chlorine, bromine or trifluoromethyl, and
X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, 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, 1-buten-3-yl-oxy-carbonyl, 2-buten-4-yl oxy-carbonyl, propargyloxycarbonyl, 1-butyn-3- yl-oxy-carbonyl, 2-Bu tin-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 for ethenyl substituted by methoxy carbonyl or ethoxycarbonyl.

The radicals listed above or listed in preferred areas definitions apply both to the end products of the formula (I) and correspondingly for the starting or intermediate products required for the production. This  Residual definitions can be between themselves, that is, between the specified ones areas can be combined as required.

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

Group 1

X _n has the meanings given in the list below:
2-hydroxy, 3-hydroxy, 4-hydroxy, 2-cyano, 3-cyano, 4-cyano, 2-carboxy, 3-carboxy, 4-carboxy, 2-fluorine, 3-fluorine, 4-fluorine, 2, 3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2-chloro, 3-chloro, 4-chloro, 2,3- Dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, 2-bromo, 3-bromo, 4-bromo, 2-methyl, 3- Methyl, 4-methyl, 2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-methoxy, 3-methoxy, 4-methoxy, 2,4-dimethoxy, 2,5-dimethoxy, 2,6-dimethoxy, 3,4-dimethoxy, 2-difluoromethoxy, 4-difluoromethoxy, 2- Trifluoromoxy, 4-trifluoromethoxy, 4-ethoxy, 4-methylthio, 4-ethylthio, 4-methoxy carbonyl, 4-ethoxycarbonyl, 4-carboxymethoxy, 4-methoxycarbonylmethoxy, 4-ethoxycarbonylmethoxy, 4-n-propoxycarbonylmethoxy, 4-i- Propoxycarbonyl methoxy, 4- (1-carboxyethoxy), 4- (1- (methoxycarbonyl) ethoxy), 4- (1- (ethoxycarbonyl) ethoxy), 4- (1- (n-propoxycarbonyl) ethoxy ), 4- (1- (i-Propoxyc arbo nyl) ethoxy), 4- (allyloxycarbonylmethoxy), 4- (1- (allyloxycarbonyl) ethoxy), 4- (propargyloxycarbonylmethoxy), 4- (1- (propargyloxycarbonyl) ethoxy), 4- (benzyl oxycarbonylmethoxy), 4- (1- (benzyloxycarbonyl) ethoxy), 4- (aminocarbonyl methoxy), 4- (methylaminocarbonylmethoxy), 4- (ethylaminocarbonylmethoxy), 4- (n-propylaminocarbonylmethoxy), 4- (1-propylaminocarbonylmethoxy), 4 - (Dimethylaminocabonylmethoxy), 4- (i- (methylaminocarbonyl) ethoxy), 4- (1- (ethylaminocarbonyl) ethoxy), 4- (1- (n-propylaminocarbonyl) ethoxy), 4- (1- (i - Propylaminocarbonyl) ethoxy), 4- (1- (dimethylaminocarbonyl) ethoxy), 4- (2-methoxycarbonylethenyl), 4- (2-ethoxycarbonylethenyl).

Group 2

X _n has the meanings given above in Group 1.

Group 3

X _n has the meanings given above in Group 1.

Group 4

X _n has the meanings given above in Group 1.

Group 5

X _n has the meanings given above in Group 1.

Group 6

X _n has the meanings given above in Group 1.

Group 7

X _n has the meanings given above in Group 1.

Group 8

X _n has the meanings given above in Group 1.

Group 9

X _n has the meanings given above in Group 1.

Group 10

X _n has the meanings given above in Group 1.

Group 11

X _n has the meanings given above in Group 1.

Group 12

X _n has the meanings given above in Group 1.

Group 13

X _n has the meanings given above in Group 1.

Group 14

X _n has the meanings given above in Group 1.

Group 15

X _n has the meanings given above in Group 1.

The new substituted phenyluracils of the general formula (I) are of interest sante biological properties. They are particularly characterized by 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 ¹ , R ² , R ³ , R ⁴ and R ^{5 have} the meaning given above and
X ^{1 represents} halogen,
with aryl compounds of the general formula (III)

in which
n, Q 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
R ² and R ^{3 have} the meaning given above and
R represents alkyl, aryl or arylalkyl,
with aryl isocyanates of the general formula (V)

in which
n, Q, R ⁴ , R ⁵ and X have the meaning given above,
or with aryl urethanes (aryl carbamates) of the general formula (VI)

in which
n, Q, R ⁵ , R ⁶ 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, Q, R ³ , R ⁴ , R ⁵ and X have the meaning given above and
R 'represents alkyl,
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, Q, R ² , R ³ , R ⁴ , R ⁵ and X have the meaning given above,
with 1-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (VIII)

X ² -A ¹ (VIII)

in which
A ^{1 represents} optionally substituted alkyl and
X ^{2 represents} halogen or the grouping -O-SO ₂ -OA ¹ ,
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 definition of the substituents.

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 → OCH ₂ COOC ₂ H ₅ , OCH (CH ₃ ) COOCH ₃ → OCH (CH ₃ ) COOH), reaction with dicyan or hydrogen sulfide (e.g. R ⁵ : Br → CN, CN → CSNH ₂ , conversion of carboxy compounds into other carboxylic acid derivatives by conventional methods (e.g. R ² : COOH → CN, CN → CSNH ₂ , COOH → COOCH ₃ , COOCH ₃ → CONH ₂ ); see the production examples).

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

If, for example, methyl [1- (2,4-dichloro-5-phenylthio-phenyl) -2,5-dioxo-2,5-di hydro-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 outlined by the following formula:

For example, if 1- [2-chloro-4-trifluoromethyl-5- (4-methoxycarbonyl-methoxy-phenoxy) -phenyl] -4-difluoromethyl-3,6-dihydro-2,6-dioxo-1 (2H) - is used pyrimidine and methyl bromide as starting materials, the course of the reaction in process (d) according to the invention can be outlined by 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 the formula (II), R ¹ , R ² , R ³ , R ⁴ and R ⁵ preferably or in particular have those meanings which are preferred or particularly in connection with the description of the compounds of the formula (I) according to the invention were preferably given for R ¹ , R ² , R ³ , R ⁴ and R ⁵ ; X ¹ preferably represents fluorine or chlorine, in particular fluorine.

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

The ver in the process (a) according to the invention as starting materials Aryl compounds are generally defined by the formula (III). In the Formula (III) has n, Q and X preferably or in particular those meaning tions already above in connection with the description of the Invention compounds of formula (I) preferably or as in particular before given for n, Q and X were given.  

The starting materials of the general formula (III) are known organic synthesis 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 ² and R ³ preferably or in particular have those meanings which, in connection with the description of the compounds of the general formula (I) according to the invention, are preferred or particularly preferred for R ² and R ³ have been specified; R preferably represents C ₁ -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 according to known processes can be prepared (cf. J. Heterocycl. Chem. 9 (1972), 513-522).

Formula (V) provides a general definition of the aryl isocyanates to be used as starting materials in process (b) according to the invention. In the general formula (V), n, Q, R ⁴ , R ⁵ and X preferably or in particular have those meanings which are preferred or as in particular in connection with the description of the compounds of the general formula (I) according to the invention have preferably been given for n, Q, R ⁴ , R ⁵ and X.

The starting materials of the general formula (V) are not yet from the literature known; as new substances, they are also the subject of the present application.

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

in which
n, Q, R ⁴ , R ⁵ and X have the meaning given above,
with phosgene in the presence of a diluent, such as. B. chlorobenzene, at temperatures between -20 ° C and + 150 ° C (see, for example. 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, Q, R ⁴ , R ⁵ and X preferably or in particular have those meanings which are preferred or particularly preferred for, in connection with the description of the compounds of the general formula (I) according to the invention n, Q, R ⁴ , R ⁵ and X have been given; R preferably represents C ₁ -C ₄ alkyl, phenyl or benzyl, in particular methyl or ethyl.

The starting materials of the general formula (VI) are not yet from the literature known; as new substances, they are also the subject of the present application.

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

in which
n, Q, R ⁴ , R ⁵ 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, such as. B. pyridine, and if appropriate in the presence of a diluent, such as. B. 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 known and / or can be produced by methods known per se (cf. Justus Liebigs Ann. Chem. 740 (1970), 169-179; US-A-3715395; US-A-3914418; DE-A-27 48 554; DE 37 36 089).

Not yet known and as new substances of the present application are the aniline derivatives of the general formula (IXa)

in which
n, R ⁴ and X have the meaning given above and
Y represents cyano, thiocarbamoyl or trifluoromethyl.

The new aniline derivatives of the general formula (IXa) are obtained if anilines of the general formula (XI)

in which
R ⁴ , X ¹ and Y have the meaning given above,
with aryl compounds of the general formula (III)

in which
n, Q 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, such as. As sodium hydride, and optionally in the presence of a diluent, such as. B. N-methyl pyrrolidone, at temperatures between 0 ° C and 150 ° C (see. Her position 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, Q, R ³ , R ⁴ , R ⁵ and X preferably or in particular have those meanings which have already been described above in connection with the description of the compounds of the general formula (I) according to the invention or have been specified as particularly preferred for n, Q, R ³ , R ⁴ , R ⁵ and X; R 'is preferably C ₁ -C ₄ alkyl, especially methyl or ethyl.

The new 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 ^{3 has} the meaning given above and
R 'represents alkyl (in particular methyl or ethyl),
with aniline derivatives of the general formula (IX)

in which
n, Q, R ⁴ , R ⁵ and X have the meaning given above,
optionally in the presence of a diluent, such as. B. 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 according to known methods can be produced (see. DE 196 04 229).  

Formula (Ia) provides a general definition of 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). In formula (Ia), n, Q, R ² , R ³ , R ⁴ , R ⁵ and X preferably or in particular have those meanings which have preferably been described above in connection with the description of the compounds of the formula (I) according to the invention or as particularly preferred for n, Q, R ² , R ³ , R ⁴ , R ⁵ and X have been given.

The starting materials of the general formula (Ia) for process (b) are new Substances also subject of the present application; you can according to the he Processes (a), (b) and (c) according to the invention can be produced.

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 formula (VIII), A ¹ preferably represents alkyl which has 1 to 4 carbon atoms and is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy and X ^{2 represents} chlorine, bromine, iodine, methylsulfonyloxy or ethylsulfonyloxy; in particular A ¹ each represents methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy and X ^{2 represents} chlorine, bromine, iodine, methyl sulfonyloxy or ethylsulfonyloxy.

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

The processes according to the invention for the preparation of the compounds of general My formula (I) are preferably made using diluents carried out. As a diluent for carrying out the inventive In addition to water, processes (a), (b), (c) and (d) primarily involve inert organic ones Solvent. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as as petrol, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether,  Hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ether like Diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol di methyl 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-methyl pyrrolidone 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 mono ethyl ether, their mixtures with water or pure water.

As reaction aids for processes (a), (b), (c) and (d) generally come the usual inorganic or organic bases or Acid acceptors into consideration. These preferably include alkali metal or earth alkali metal, acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as 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, n or i propanolate, n, i, -s or -t-butanolate; also basic organic nitrogen compounds, such as for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-di- isopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclo hexylamine, 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, benzyl trimethylammonium, benzyl trimethylammonium, benzyl trimethylammonium hydroxide, benzyl-triethylammonium-hydroxide, benzyl-tributyl ammonium-chloride, benzyl-tributylammonium-bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium-chloride, tributyl-hexadecylphosphonium-bromide, butyl-triphenylphosphonium-bromide-ethylphosphonium-bromide, .

The reaction temperatures can be carried out when carrying out the inventive Processes (a), (b), (c) and (d) can be varied over a wide range. Generally I think one works at 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 guided. However, it is also possible to use the method according to the invention high or reduced pressure - generally between 0.1 bar and 10 bar - to be carried out.

To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible Lich to use one of the components in a larger excess. The order settlement is generally in a suitable diluent in the presence carried out a reaction auxiliary and the reaction mixture is in all agitated several hours at the required temperature. The on  work is carried out according to customary methods (cf. games).

The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are found in places grow where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used. The active compounds according to the invention can, for. B. ver in the following plants be applied:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

Dicot cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, lactuca, cucumis, cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, sorghum, panicum, saccharum, pineapple, asparagus, allium.  

The use of the active compounds according to the invention is by no means limited to these Limited genres, but extends in the same way to others Plants.

Depending on the concentration, the compounds are suitable for the total weed control z. B. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the connections to weed beds fighting in permanent crops, e.g. B. forest, ornamental wood, fruit, wine, citrus, nut, Banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hops plants, on ornamental and sports turf and pastures and for selective weeds fighting in annual crops.

The compounds of formula (I) according to the invention show strong herbicidal activity solvency and a wide range of effects when used on and on the floor aerial parts of plants. To a certain extent, they are also suitable for selective use Control of monocot and dicot weeds in monocot and di cotyledon cultures both pre-emergence and post-emergence.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient im impregnated natural and synthetic materials as well as very fine encapsulation in polymers Fabrics.

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

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. 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.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and 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 foam Generating funds are possible: z. B. non-ionic and anionic emulsions goals such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants come into question: z. B. lignin sulfite and Methyl cellulose.

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

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan 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 Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are 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), Bromo butide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyonaz, Chloramben, Chloramben, Chloramben, Chloramben, Chloramben, Chloramben, Chloramben, (-ethyl), chloronitrofen, chlorsulfuron, chlortoluron, Cini don (-ethyl), cinmethylin, cinosulfuron, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron (-methyl), clorylsulam (-me) , Cyanazines, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxy dim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), difenzoquat, diflufenican, diflu fenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epo prodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid (-ethylprop), -Penoxaprop (-methyl) isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Fluazi fop (-P-butyl), Fluazolate, Flucarbazone, Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsuron, Flumetsulam , Fluorochloridone, Fluoro glycofen (-ethyl), Flupoxam, Flupropacil, Flurpyrsulfiiron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Flu thiacet (-methyl), Fluthiamide Fomesafen, Glufosinate (-ammonium), Glyphosa te (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin , Imazosulturon, Iodosulfuron, Ioxynil, Iso propalin, Isoproturon, Isouron, Isoxaben, Isoxachlort ole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metola chlor, Metosulain, Metoxinon, Mulfuron-Metruron, Metruron, Metruron, Metrurin, Metrurin, Metrurin, Metrurin , Mono linuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orben carb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenophipethilone, phenmedipynil, phephmediphamet, phenmedipynet, phephmediphamet, phenmedipynet, phenmedipynet, phe mediphamil, phe , Propachlor, propanil, propaquiza fop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridate, pyriminobac (-methyl), pyrithiobium Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefuryl), Rimsulfuron, Sethoxy dim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, tebuthiuron, tepraloxydim, terbuthylazine, ter butryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, triben uronidiflonluronidlonluron (l).

A mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellants, plants nutrients and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use  Solutions, suspensions, emulsions, powders, pastes and granules are used become. The application is done in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after emergence of the plants are applied. They can also be planted in the soil before sowing be working.

The amount of active ingredient used can vary over a wide range. she depends essentially 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 area, preferably between 5 g and 5 kg per ha.

The manufacture and use of the active compounds according to the invention start out the following examples.

Manufacturing examples

example 1

Procedure (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-1 (2H) -pyrimidin-1-yl) -2,5-difluoro-benzonitrile are added . The reaction mixture is stirred at 60 ° C. for 18 hours and then poured onto approximately the same volume of 1N 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 chromatography (silica gel, chloroform / ethyl acetate, vol .: 2: 1). The first fraction obtained 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) -pyrimidin-1-yl) -5-fluoro-2- (4-methoxy-phenoxy) -benzonitrile, 0.20 g (1.8 mmol) of dimethyl sulfate, 0.30 g (2.4 mmol) of potassium carbonate and 100 ml of acetone are heated under reflux for 15 hours and then concentrated in a water jet vacuum. The residue is shaken with 50 ml of 1N 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- fluoro-2- (4-methoxy-phenoxy) -benzonitrile with a melting point of 62 ° C.

Analogous to preparation examples 1 and 2 and in accordance with the general Description of the manufacturing method according to the invention can for example also the compounds of the formula (I) listed in Table 1 below getting produced.  

Table 1

Examples of the compounds of the formula (I)

Starting materials of the formula (VI)

Example (VI-1)

2.8 g (11 mmol) of 1-amino-4-cyano-2-fluoro-5- (4-methoxyphenoxy) benzene are placed in 100 ml of methylene chloride with 1.7 g of 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 1N hydrochloric acid. The organic phase is concentrated in a water jet vacuum, the residue was crystallized with diethyl ether / diisopropyl ether and the solid product was isolated by suction.
1.2 g (34% of theory) of N- (4-cyano-2-fluoro-5- (4-methoxyphenoxy) phenyl) O-ethyl carbamate are obtained.
¹ H 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, the mixture 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 1-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, those in the following can also be used Compounds of the general formula (IX) listed in Table 2 are prepared become.

Table 2

Examples of the compounds of the formula (IX)

Examples of use Example A Pre-emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether.

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

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

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 example 4 show and 6 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.

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

With the active ingredient preparation, test plants are sprayed, which is a height of 5-15 cm so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l water / ha the desired amounts of active ingredient are applied.

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 example 4 show and 6 strong action against weeds.

Claims (17)

1. Substituted phenyluracils of the general formula (I)
in which
n stands for the numbers 0, 1, 2, 3, 4 or 5,
Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH or N (alkyl),
R ^{1 represents} hydrogen, amino or optionally substituted alkyl,
R ^{2 represents} carboxy, cyano, carbamoyl, thiocarbamoyl or optionally substituted alkyl or alkoxycarbonyl,
R ^{3 represents} hydrogen, halogen or optionally substituted alkyl,
R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,
R ^{5 represents} cyano, carbamoyl, thiocarbamoyl, halogen or, where appropriate, optionally substituted alkyl or alkoxy, and
X for hydroxyl, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylamino carbonyl, dialkylaminocarbonyl, Alkylcarbonylamino, alkoxy carbonylamino, alkylsulfonylamino, alkenyl, alkenyloxy, alkenyl oxycarbonyl, alkynyl, alkynyloxy or alkynyloxycarbonyl, where in the event that n is greater than 1, X in the individual possible compounds may also have various of the meanings given. 2. Substituted phenyluracile according to claim 1, characterized in that
n stands for the numbers 0, 1, 2, 3 or 4,
Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH or N (C ₁ -C ₄ alkyl),
R ¹ represents hydrogen, amino or optionally cyano-, carboxyl-, fluorine-, chlorine-, C ₁ -C ₄ alkoxy or C ₁ -C ₄ -alkoxy-carbonyl substitu iertes C ₁ -C ₄ alkyl,
R ^{2 represents} carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by cyano, fluorine, chlorine or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy-carbonyl,
R ^{3 represents} hydrogen, fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl optionally substituted by fluorine or chlorine,
R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine,
R ^{5 represents} cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or in each case optionally substituted by fluorine and / or chlorine substituted by C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, and
X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, for each optionally by hydroxy, cyano, carboxy, carbamoyl, fluorine, chlorine, C ₁ -C ₄ -alkoxy , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkyl sulfonyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₂ -C ₄ -Al kenyloxycarbonyl, C ₂ -C ₄ -alkynyloxycarbonyl, C ₁ -C ₄ -alkylamino-carbonyl, di- (C ₁ -C ₄ -alkyl) -amino-carbonyl or benzyloxycarbonyl-substituted alkyl, alkoxy , Alkylthio, alkylsulfinyl, alkyl sulfonyl or alkylamino each having 1 to 6 carbon atoms, for dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, for each optionally substituted by cyano, fluorine, chlorine, bromine or C ₁ -C ₄ alkoxy-substituted alkylcarbonyl , Alkoxycarbonyl or alkylaminocarbonyl each having 1 to 6 carbon atoms in the alkyl groups, for dialkylaminocarbonyl having 1 to 6 carbon atoms in the alkyl groups, for each given enenfalls substituted by fluorine, chlorine or bromine, alkylcarbonylamino, alkoxycarbonyl amino, alkylsulfonylamino, or in each case optionally cyano-, carboxyl-, fluorine-, chlorine-, bromine or C ₁ -C ₄ -alkoxy-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkynyl, alkynyloxy or Alkynyloxycarbonyl, each with up to 6 carbon atoms. 3. Substituted phenyluracile according to claim 1, characterized in that
n represents the numbers 1, 2 or 3,
Q represents O (oxygen), S (sulfur), SO, SO ₂ , NH or N (CH ₃ ),
R ^{1 represents} hydrogen, amino or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
R ^{2 represents} carboxy, cyano, carbamoyl, thiocarbamoyl or in each case methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
R ^{3 represents} hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl or trifluoromethyl, and
X for hydroxy, mercapto, amino, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, for each optionally by cyano, carboxy, carbamoyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio , Ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, allyloxycarbonyl, 1-butene-3- yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butyn-3-yl-oxycarbonyl, 2-butyn-4-yl-oxy-carbonyl, methylaminocarbonyl, ethyl aminocarbonyl, n- or i-propylamino-carbonyl, dimethylamino carbonyl, diethylamino-carbonyl, phenoxycarbonyl, benzyloxy carbonyl, 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 each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i -Propoxy-substituted acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, for dimethylaminocarbonyl or diethyl aminocarbonyl, each optionally substituted by fluorine or chlorine Acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxy carbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfon ethenyl, propenyl, propenyloxy, propenyloxycarbonyl, ethynyl, propynyl, propynyloxy or propynyloxycarbonyl, optionally substituted by cyano, carboxy, fluorine, chlorine, methoxycarbonyl or ethoxycarbonyl does. 4. Substituted phenyluracils according to claim 1, characterized by the general formula (IA),
in which
R ^{1 represents} hydrogen, amino or methyl,
R ^{2 represents} trifluoromethyl, chlorodifluoromethyl, difluoromethyl or penta-fluoroethyl,
R ^{3 represents} hydrogen, chlorine or methyl,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} cyano or thiocarbamoyl, 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-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butyn-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, Methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl or ethoxycarbonyl, or represents ethenyl substituted by methoxy carbonyl or ethoxycarbonyl. 5. Substituted phenyluracile according to claim 4, characterized in that
R ^{1 represents} methyl,
R ^{2 represents} trifluoromethyl, chlorodifluoromethyl, difluoromethyl or penta-fluoroethyl,
R ^{3 represents} hydrogen, chlorine or methyl,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} fluorine, chlorine, bromine or trifluoromethyl, 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-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butyn-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, Methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl or ethoxycarbonyl, or represents ethenyl substituted by methoxy carbonyl or ethoxycarbonyl. 6. Substituted phenyluracile according to claim 4, characterized in that
R ^{1 represents} hydrogen, amino or methyl,
R ^{2 represents} carboxy, cyano, carbamoyl, thicarbamoyl, methoxycarbonyl or ethoxycarbonyl,
R ^{3 represents} hydrogen, chlorine or methyl,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} cyano, thiocarbamoyl, fluorine, chlorine, bromine or trifluoromethyl, 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-buten-3-yl-oxy-carbonyl, 2-buten-4-yl-oxy-carbonyl, propargyloxycarbonyl, 1-butyn-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, Methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl or ethoxycarbonyl, or represents ethenyl substituted by methoxy carbonyl or ethoxycarbonyl. 7. Substituted phenyluracile according to any one of claims 1 to 6, characterized characterized in that n stands for 1. 8. Substituted phenyluracile according to one of claims 1 to 7, characterized in that R ^{2 represents} trifluoromethyl. 9. Substituted phenyluracile according to one of claims 1 to 8, characterized in that R ^{4 is} fluorine. 10. Substituted phenyluracile according to one of claims 1 to 9, characterized in that R ^{5 is} cyano or thiocarbamoyl. 11. A process for the preparation of substituted phenyluracils according to any one of claims 1 to 10, characterized in that

• (a) Halogenophenyluracils of the general formula (II)
  in which
  R ¹ , R ² , R ³ , R ⁴ and R ^{5 have} the meaning given in one of claims 1 to 10 and
  X ^{1 represents} halogen,
  with aryl compounds of the general formula (III)
  in which
  n, Q and X have the meaning given in one of claims 1 to 10,
  - 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 that one
• (b) aminoalkenates of the general formula (IV)
  in which
  R ² and R ^{3 have} the meaning given in one of claims 1 to 10 and
  R represents alkyl, aryl or arylalkyl,
  with aryl isocyanates of the general formula (V)
  in which
  n, Q, R ⁴ , R ⁵ and X have the meaning given in one of claims 1 to 10,
  or with aryl urethanes (aryl carbamates) of the general formula (VI)
  in which
  n, Q, R ⁵ , R ⁶ and X have the meaning given in one of claims 1 to 10 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 that one
• (c) N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII)
  in which
  n, Q, R ³ , R ⁴ , R ⁵ and X have the meaning given in one of claims 1 to 10 and
  R 'represents alkyl,
  reacted with a metal hydroxide in the presence of water and optionally in the presence of an organic solvent,
  or that one
• (d) substituted phenyluracils of the general formula (Ia)
  in which
  n, Q, R ² , R ³ , R ⁴ , R ⁵ and X have the meaning given in one of claims 1 to 10,
  with 1-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (VIII)
  X ² -A ¹ (VIII)
  in which
  A ^{1 represents} optionally substituted alkyl and
  X ^{2 represents} halogen or the grouping -O-SO ₂ -OA ¹ ,
  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 in the course of the substituent definition.

12. Aryl isocyanates of the general formula (V)
in which
n, Q, R ⁴ , R ⁵ and X have the meaning given in one of claims 1 to 7, 9 and 10. 13. Aryl urethanes (aryl carbamates) of the general formula (VI)
in which
n, Q, R ⁵ , R ⁶ and X have the meaning given in one of claims 1 to 7 and 10 and
R represents alkyl, aryl or arylalkyl. 14. Aniline derivatives of the general formula (IXa)
in which
n, R ⁴ and X have the meaning given in one of claims 1 to 7 and 9 and
Y represents cyano, thiocarbamoyl or trifluoromethyl. 15. Substituted phenyluracils of the general formula (Ia)
in which
n, Q, R ² , R ³ , R ⁴ , R ⁵ and X have the meaning given in one of claims 1 to 10. 16. Use of at least one substituted phenyluracil according to one of claims 1 to 10 for controlling unwanted plants. 17. Herbicidal agent, characterized by the content of at least one substituted phenyluracil according to any one of claims 1 to 10.