U.S. patent application number 10/629450 was filed with the patent office on 2004-02-05 for substituted phenyluracils.
Invention is credited to Andree, Roland, Dahmen, Peter, Drewes, Mark Wilhelm, Feucht, Dieter, Linker, Karl-Heinz, Pontzen, Rolf, Schwarz, Hans-Georg.
Application Number | 20040023805 10/629450 |
Document ID | / |
Family ID | 7637651 |
Filed Date | 2004-02-05 |
United States Patent
Application |
20040023805 |
Kind Code |
A1 |
Andree, Roland ; et
al. |
February 5, 2004 |
Substituted phenyluracils
Abstract
Phenyluracils of the general formula (I) 1 in which Q, R.sup.1,
R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 each have one of the
meanings given in the description, and processes for their
preparation and their use as herbicides.
Inventors: |
Andree, Roland; (Langenfeld,
DE) ; Schwarz, Hans-Georg; (Langenfeld, DE) ;
Linker, Karl-Heinz; (Leverkusen, DE) ; Drewes, Mark
Wilhelm; (Langenfeld, DE) ; Dahmen, Peter;
(Neuss, DE) ; Feucht, Dieter; (Monheim, DE)
; Pontzen, Rolf; (Leichlingen, DE) |
Correspondence
Address: |
BAYER CROPSCIENCE LP
Patent Department
100 BAYER ROAD
PITTSBURGH
PA
15205-9741
US
|
Family ID: |
7637651 |
Appl. No.: |
10/629450 |
Filed: |
July 29, 2003 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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10629450 |
Jul 29, 2003 |
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10019842 |
Feb 20, 2002 |
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6649760 |
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10019842 |
Feb 20, 2002 |
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PCT/EP01/03332 |
Mar 23, 2001 |
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Current U.S.
Class: |
504/243 ;
544/309 |
Current CPC
Class: |
C07D 239/34 20130101;
C07D 403/12 20130101; C07D 239/54 20130101; C07D 401/12 20130101;
C07D 239/557 20130101 |
Class at
Publication: |
504/243 ;
544/309 |
International
Class: |
A01N 043/54; C07D
239/02 |
Foreign Application Data
Date |
Code |
Application Number |
Apr 5, 2000 |
DE |
100 16 893.0 |
Claims
1. Substituted phenyluracils of the general formula (I) 117in which
Q represents O (oxygen), S (sulphur), SO or SO.sub.2, R.sup.1
represents hydrogen, amino, optionally cyano-, halogen- or
C.sub.1-C.sub.4-alkoxy-su- bstituted alkyl having 1 to 4 carbon
atoms or in each case optionally halogen-substituted alkenyl or
alkinyl having in each case 2 to 4 carbon atoms, R.sup.2 represents
cyano, carboxyl, carbamoyl, thiocarbamoyl or in each case
optionally cyano-, halogen- or C.sub.1-C.sub.4-alkoxy-substitut- ed
alkyl or alkoxy-carbonyl having in each case 1 to 4 carbon atoms,
R.sup.3 represents hydrogen, halogen or optionally
halogen-substituted alkyl having 1 to 4 carbon atoms, R.sup.4
represents hydrogen, nitro, cyano or halogen, R.sup.5 represents
cyano, thiocarbamoyl, bromine or in each case optionally
halogen-substituted alkyl or alkoxy having in each case 1 to 4
carbon atoms, and R.sup.6 represents an optionally nitro-,
hydroxyl-, mercapto-, amino-, cyano-, carboxyl-, carbamoyl-,
halogen-, C.sub.1-C.sub.4-alkyl-, cyano-C.sub.1-C.sub.4-alkyl-,
carboxyl-C.sub.1-C.sub.4-alkyl-, C.sub.1-C.sub.4-halogenoalkyl-,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl-,
C.sub.1-C.sub.4-alkoxy-car- bonyl-C.sub.1-C.sub.4-alkyl-,
C.sub.1-C.sub.4-alkylaminocarbonylalkyl-,
di-(C.sub.1-C.sub.4-alkyl)-aminocarbonylalkyl-,
C.sub.1-C.sub.4-alkoxy-, cyano-C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-halogenoalkoxy-,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkoxy-,
carboxyl-C.sub.1-C.sub.4-- alkoxy-,
C.sub.1-C.sub.4-alkoxy-carbonyl-C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-alkylaminocarbonyl-C.sub.1-C.sub.4-alkoxy-,
di-(C.sub.1-C.sub.4-alkyl)-aminocarbonyl-C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-alkoxy-carbonyl-, C.sub.2-C.sub.4-alkenyloxy-,
C.sub.2-C.sub.4-alkinyloxy-, C.sub.1-C.sub.4-alkylthio-,
C.sub.1-C.sub.4-halogenoalkylthio-,
C.sub.1-C.sub.4-alkylsulphinyl-,
C.sub.1-C.sub.4-halogenoalkylsulphinyl-,
C.sub.1-C.sub.4-alkylsulphonyl-,
C.sub.1-C.sub.4-halogenoalkylsulphonyl-,
C.sub.1-C.sub.4-alkylcarbonyl-am- ino-,
C.sub.1-C.sub.4-alkoxy-carbonyl-amino- or
C.sub.1-C.sub.4-alkylsulph- onyl-amino-substituted
nitrogen-containing heterocyclic grouping from the group consisting
of pyrrolyl, pyrazolyl, imidazolyl, triazolyl, triazolinyl,
pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl,
benzoxazolyl, benzothiazolyl, quinolinyl, quinazolinyl,
quinoxalinyl, including all possible tautomeric forms of the
compounds of the general formula (I) and the possible salts and
acid or base adducts of the compounds of the general formula
(I).
2. Compounds according to claim 1, characterized in that Q
represents O (oxygen), S (sulphur) or SO.sub.2, R.sup.1 represents
hydrogen, amino, in each case optionally cyano-, fluorine-,
chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or
i-propyl, or in each case optionally fluorine- and/or
chlorine-substituted propenyl or propinyl, R.sup.2 represents
cyano, carboxyl, carbamoyl, thiocarbamoyl or in each case
optionally cyano-, fluorine-, chlorine-, methoxy- or
ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl,
ethoxycarbonyl, n- or i-propoxycarbonyl, R.sup.3 represents
hydrogen, fluorine, chlorine, bromine or in each case optionally
fluorine- and/or chlorine-substituted methyl, ethyl, n- or
i-propyl, R.sup.4 represents hydrogen, cyano, fluorine, chlorine or
bromine, R.sup.5 represents cyano, thiocarbamoyl, bromine or in
each case optionally fluorine- and/or chlorine-substituted methyl,
ethyl, methoxy or ethoxy, and R.sup.6 represents an in each case
optionally nitro-, hydroxyl-, amino-, cyano-, carboxyl-,
carbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or
i-propyl-, n-, i-, s- or t-butyl-, chloromethyl-, fluoromethyl-,
dichloromethyl-, difluoromethyl-, trichloromethyl-,
trifluoromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-,
chloroethyl-, fluoroethyl-, dichloroethyl-, difluoroethyl,
chlorofluoroethyl-, trichloroethyl-, trifluoroethyl-,
chlorodifluoroethyl-, fluorodichloroethyl-, tetrafluoroethyl-,
chlorotrifluoroethyl-, pentafluoroethyl-, chloro-n-propyl-,
fluoro-n-propyl-, chloro-1-propyl-, fluoro-1-propyl-,
dichloropropyl-, difluoropropyl-, trichloropropyl-,
trifluoropropyl-, cyanomethyl-, cyanoethyl-, cyanopropyl-,
carboxymethyl-, carboxyethyl-, carboxypropyl-, methoxymethyl-,
ethoxymethyl-, propoxymethyl-, methoxyethyl-, ethoxyethyl-,
methoxycarbonylmethyl-, ethoxycarbonylmethyl-, n- or
i-propoxycarbonylmethyl-, methylaminocarbonylmethyl-,
ethylaminocarbonylmethyl-, dimethylaminocarbonylmethyl-,
methoxycarbonylethyl-, ethoxycarbonylethyl-, n- or
i-propoxycarbonylethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-,
i-, s- or t-butoxy-, difluoromethoxy-, trifluoromethoxy-,
chlorodifluoromethoxy-, carboxymethoxy-, carboxyethoxy-,
methoxycarbonylmethoxy-, ethoxycarbonylmethoxy-, n- or
i-propoxycarbonylmethoxy-, methylaminocarbonylmethoxy-,
ethylaminocarbonylmethoxy-, dimethylaminocarbonylmethoxy-,
methoxycarbonylethoxy-, ethoxycarbonylethoxy-, n- or
i-propoxycarbonylethoxy-, methylaminocarbonylethoxy-,
ethylaminocarbonylethoxy-, dimethylaminocarbonylethoxy-,
methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-,
propenyloxy-, butenyloxy-, propinyloxy-, butinyloxy-, methylthio-,
ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-,
difluoromethylthio-, trifluoromethylthio-,
chlorodifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, n- or
i-propylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-,
ethylsulphonyl-, n- or i-propylsulfonyl-,
trifluoromethylsulphonyl-, acetylamino-, propionylamino-, n- or
i-butyroylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, n-
or i-propoxycarbonylamino-, methylsulphonylamino-,
ethylsulphonylamino-, n- or i-propylsulphonylamino-substituted
nitrogen-containing heterocyclic grouping form the group consisting
of pyrrolyl, pyrazolyl, imidazolyl, triazolyl, triazolinyl,
pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl,
benzoxazolyl, benzothiazolyl, quinolinyl, quinazolinyl,
quinoxalinyl.
3. Compounds according to claim 1 or 2, characterized in that Q
represents O (oxygen) or S (sulphur), R.sup.1 represents hydrogen,
amino or represents in each case optionally fluorine-, chlorine-,
methoxy- or ethoxy-substituted methyl or ethyl, R.sup.2 represents
cyano, carboxyl, carbamoyl or in each case optionally fluorine-
and/or chlorine-substituted methyl, ethyl, methoxycarbonyl or
ethoxycarbonyl, R.sup.3 represents hydrogen, fluorine, chlorine,
bromine or in each case optionally fluorine- and/or
chlorine-substituted methyl or ethyl, R.sup.4 represents hydrogen,
fluorine or chlorine, R.sup.5 represents cyano, thiocarbamoyl,
bromine or trifluoromethyl, and R.sup.6 represents an in each case
optionally nitro-, hydroxyl-, amino-, cyano-, carboxyl-,
carbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or
i-propyl-, n-, i-, s- or t-butyl-, dichloromethyl-,
difluoromethyl-, trichloromethyl-, trifluoromethyl-,
chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n-
or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-,
trifluoromethoxy-, chlorodifluoromethoxy-, carboxymethoxy-,
carboxyethoxy-, methoxycarbonylmethoxy-, ethoxycarbonylmethoxy-, n-
or i-propoxycarbonylmethoxy-, methoxycarbonylethoxy-,
ethoxycarbonylethoxy-, n- or i-propoxycarbonylethoxy-,
methoxycarbonyl-, ethoxycarbonyl-, propenyloxy-, butenyloxy-,
propinyloxy-, butinyloxy-, methylthio-, ethylthio-, n- or
i-propylthio-, n-, i-, s- or t-butylthio-, difluoromethylthio-,
trifluoromethylthio-, chlorodifluoromethylthio-, methylsulphinyl-,
ethylsulphinyl-, n- or i-propylsulphinyl-,
trifluoromethylsulphinyl-, methylsulphonyl, ethylsulphonyl-, n- or
i-propylsulphonyl-, trifluoromethylsulphonyl-, acetylamino-,
propionylamino-, n- or i-butyroylamino-, methoxycarbonylamino-,
ethoxycarbonylamino-, n- or i-propoxycarbonylamino-,
methylsulphonylamino-, ethylsulphonylamino-, n- or
i-propylsulphonylamino-substituted nitrogen-containing heterocyclic
grouping from the group consisting of pyrrolyl, pyrazolyl,
imidazolyl, triazolyl; triazolinyl, pyridinyl, pyrazinyl,
pyridazinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl,
quinolinyl, quinazolinyl, quinoxalinyl.
4. Compounds according to any of claims 1 to 3, characterized in
that R.sup.1 represents hydrogen, amino, methyl or ethyl, R.sup.2
represents cyano or trifluoromethyl, R.sup.3 represents hydrogen,
chlorine or methyl, R.sup.5 represents cyano, thiocarbamoyl or
bromine, and R.sup.6 represents in each case optionally hydroxyl-,
amino-, cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-,
bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,
dichloromethyl-, difluoromethyl-, trichloromethyl-,
trifluoromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-,
methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-,
trifluoromethoxy-, chlorodifluoromethoxy-, carboxymethoxy-,
carboxyethoxy-, methoxycarbonylmethoxy-, ethoxycarbonylmethoxy-, n-
or i-propoxycarbonylmethoxy-, methoxycarbonylethoxy-,
ethoxycarbonylethoxy-, n- or i-propoxycarbonylethoxy-,
methoxycarbonyl-, ethoxycarbonyl-, propenyloxy-, butenyloxy-,
propinyloxy-, butinyloxy-, methylthio-, ethylthio-, n- or
i-propylthio-, difluoromethylthio-, trifluoromethylthio-,
chlorodifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, n- or
i-propylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-,
ethylsulphonyl-, n- or i-propylsulfonyl-,
trifluoromethylsulphonyl-, acetylamino-, propionylamino-, n- or
i-butyroylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, n-
or i-propoxycarbonylamino-, methylsulphonylamino-,
ethylsulphonylamino-, n- or i-propylsulphonylamino-substituted
pyrazolyl, pyridinyl, pyrimidinyl, triazinyl or benzoxazolyl.
5. Compounds according to any of claims 1 to 4, characterized in
that R.sup.1 represents hydrogen, amino or methyl, R.sup.2
represents trifluoromethyl, R.sup.5 represents cyano or bromine,
and R.sup.6 represents in each case optionally hydroxyl-, amino-,
cyano-, fluorine-, chlorine-, methyl-, ethyl-, trichloromethyl-,
methoxy- or ethoxy-substituted pyrazolyl, pyridinyl, pyrimidinyl or
benzoxazolyl.
6. Compounds according to any of claims 1 to 5, characaterized in
that Q represents O (oxygen).
7. Process for preparing compounds according to any of claims 1 to
6, characterized in that (a) phenyluracils of the general formula
(II) 118 in which Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5
are each as defined in any of claims 1 to 6 are reacted with
compounds of the general formula (III) X.sup.1--R.sup.6 (III) in
which R.sup.6 is as defined in any of claims 1 to 5 and X.sup.1
represents halogen or alkylsulphonyl, if appropriate in the
presence of a reaction auxiliary and if appropriate in the presence
of a diluent, or that (b) halogenophenyluracils of the general
formula (IV) 119 in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and
R.sup.5 are each as defined in any of claims 1 to 5 and X.sup.2
represents halogen are reacted with compounds of the general
formula (V) M-Q-R.sup.6 (V) in which Q and R.sup.6 are each as
defined in any of claims 1 to 6 and M represents hydrogen or a
metal equivalent, if appropriate in the presence of a reaction
auxiliary and if appropriate in the presence of a diluent, or that
(c) aminoalkenoic acid esters of the general formula (VI) 120 in
which R.sup.1, R.sup.2 and R.sup.3 are each as defined in any of
claims 1 to 5 and R represents alkyl, aryl or arylalkyl, are
reacted with substituted phenyl isocyanates of the general formula
(VII) 121 in which Q, R.sup.4, R.sup.5 and R.sup.6 are each as
defined in any of claims 1 to 6 or with substituted phenylurethanes
(phenylcarbamates) of the general formula (VIII) 122 in which Q,
R.sup.4, R.sup.5 and R.sup.6 are each as defined in any of claims 1
to 6 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 (d) substituted
N-phenyl-1-alkoxycarbonylamino-maleimides of the general formula
(IX) 123 in which Q, R.sup.4, R.sup.5 and R.sup.6 are each as
defined in any of claims 1 to 6 and R' represents alkyl are reacted
with a metal hydroxide in the presence of water and, if appropriate
in the presence of an organic solvent, or that (e) substituted
phenyluracils of the general formula (Ia) 124 in which Q, R.sup.2,
R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each as defined in any of
claims 1 to 6 are reacted with 1-aminooxy-2,4-dinitro-benzene or
2-aminooxysulphonyl-1,3,5-trimethylbenzene or with alkylating
agents of the general formula (X) X.sup.3-A.sup.1 (X) in which
A.sup.1 represents optionally cyano-, halogen- or
C.sub.1-C.sub.4-alkoxy-substituted alkyl having 1 to 4 carbon atoms
or in each case optionally halogen-substituted alkenyl or alkinyl
having in each case 2 to 4 carbon atoms, and X.sup.3 represents
halogen or the grouping --O--SO.sub.2--O-A.sup.1, if appropriate in
the presence of a reaction auxiliary and if appropriate in the
presence of a diluent, and electrophilic or nucleophilic and/or
oxidation or reduction reactions within the scope of the definition
of the substituents are, if appropriate, subsequently carried out
in a customary manner.
8. Compounds of the formula (VII) 125in which Q, R.sup.4, R.sup.5
and R.sup.6 are each as defined in any of claims 1 to 6.
9. Process for preparing compounds according to claim 8,
characterized in that aniline derivatives of the general formula
(XI) 126in which Q, R.sup.4, R.sup.5 and R.sup.6 are each as
defined in any of claims 1 to 6 are reacted with phosgene in the
presence of a diluent, such as, for example, chlorobenzene, at
temperatures between -20.degree. C. and +150.degree. C.
10. Compounds of the formula (VIII) 127in which Q, R.sup.4,
R.sup.5, R.sup.6 and R are each as defined in any of claims 1 to
7.
11. Process for preparing compounds according to claim 10,
characterized in that aniline derivatives of the general formula
(XI) 128in which Q, R.sup.4, R.sup.5 and R.sup.6 are each as
defined in any of claims 1 to 6 are reacted with chlorocarbonyl
compounds of the general formula (XII) RO--CO--Cl (XII) in which R
represents alkyl, aryl or arylalkyl, if appropriate in the presence
of an acid acceptor, such as, for example, pyridine, and if
appropriate in the presence of a diluent, such as, for example,
methylene chloride, at temperatures between -20.degree. C. and
+100.degree. C.
12. Compounds of the formula (XIa) 129in which Q, R.sup.4 and
R.sup.6 are each as defined in any of claims 1 to 6 and Y
represents cyano, thiocarbamoyl or trifluorormethyl.
13. Process for preparing compounds according to claim 12,
characterized in that (.alpha.) anilines of the general formula
(XIII) 130 in which Q, R.sup.4 and Y are each as defined in any of
claims 1 to 6 and 12 are reacted with compounds of the general
formula (III) X.sup.1--R.sup.6 (III) in which R.sup.6 and X.sup.1
are each as defined in any of claims 1 to 5 and 7, if appropriate
in the presence of an acid acceptor, such as, for example,
potassium hydroxide, potassium carbonate or pyridine, and if
appropriate in the presence of a diluent, at temperatures between
0.degree. C. and 200.degree. C., or that (.beta.) anilines of the
general formula (XIV) 131 in which R.sup.4, X.sup.2 and Y are each
as defined in any of claims 1 to 5, 7 and 12 are reacted with
compounds of the general (V) M-Q-R.sup.6 (V) in which M, Q and
R.sup.6 are each as defined in any of claims 1 to 7, if appropriate
in the presence of an acid acceptor and if appropriate in the
presence of a diluent, at temperatures between 0.degree. C. and
200.degree. C.
14. Compounds of the formula (IX) 132in which Q, R.sup.4, R.sup.5
and R.sup.6 are each as defined in any of claims 1 to 6 and R'
represents alkyl.
15. Process for preparing compounds according to claim 14,
characterized in that alkyl (2,5-di
oxo-2,5-dihydro-furan-3-yl)-carbamates of the general formula 133in
which R.sup.3 is as defined in any of claims 1 to 5 and R'
represents alkyl are reacted with aniline derivatives of the
general formula (XI) 134 in which Q, R.sup.4, R.sup.5 and R.sup.6
are each as defined in any of claims 1 to 6, if appropriate in the
presence of a diluent, at temperatures between 0.degree. C. and
200.degree. C.
16. Compounds of the formula (Ia) 135in which Q, R.sup.2, R.sup.3,
R.sup.4, R.sup.5 and R.sup.6 are each as defined in any of claims 1
to 6.
17. Herbicidal compositions, characterized in that they comprise at
least one compound according to any of claims 1 to 6 and customary
extenders.
18. Use of at least one compound according to any of claims 1 to 6
or a composition according to claim 17 for controlling undesirable
plants.
Description
[0001] The invention relates to novel substituted phenyluracils, to
processes for their preparation and to their use as crop treatment
agents, in particular as herbicides.
[0002] It is known that certain substituted phenyluracils have
herbicidal properties (cf. EP 408382/US 5084084/US
5127935/US5154755, EP 563384, EP 648749, U.S. Pat. Nos. 4,979,982,
5,169,430, WO 91/00278, WO-A-97/01541, WO-A-00/02866,
WO-A-98/41093). However, these compounds have hitherto not attained
significant importance.
[0003] This invention, accordingly, provides the novel substituted
phenyluracils of the general formula (I) 2
[0004] in which
[0005] Q represents O (oxygen), S (sulphur), SO or SO.sub.2,
[0006] R.sup.1 represents hydrogen, amino, optionally cyano-,
halogen- or C.sub.1-C.sub.4-alkoxy-substituted alkyl having 1 to 4
carbon atoms or in each case optionally halogen-substituted alkenyl
or alkinyl having in each case 2 to 4 carbon atoms,
[0007] R.sup.2 represents cyano, carboxyl, carbamoyl, thiocarbamoyl
or in each case optionally cyano-, halogen- or
C.sub.1-C.sub.4-alkoxy-substitut- ed alkyl or alkoxy-carbonyl
having in each case 1 to 4 carbon atoms,
[0008] R.sup.3 represents hydrogen, halogen or optionally
halogen-substituted alkyl having 1 to 4 carbon atoms,
[0009] R.sup.4 represents hydrogen, nitro, cyano or halogen,
[0010] R.sup.5 represents cyano, thiocarbamoyl, bromine or in each
case optionally halogen-substituted alkyl or alkoxy having in each
case 1 to 4 carbon atoms, and
[0011] R.sup.6 represents an optionally nitro-, hydroxyl-,
mercapto-, amino-, cyano-, carboxyl-, carbamoyl-, halogen-,
C.sub.1-C.sub.4-alkyl-, cyano-C.sub.1-C.sub.4-alkyl-,
carboxyl-C.sub.1-C.sub.4-alkyl-, C.sub.1-C.sub.4-halogenoalkyl-,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-al- kyl-,
C.sub.1-C.sub.4-alkoxycarbonyl-C.sub.1-C.sub.4-alkyl-,
C.sub.1-C.sub.4-alkylaminocarbonylalkyl-,
di-(C.sub.1-C.sub.4-alkyl)-amin- ocarbonylalkyl-,
C.sub.1-C.sub.4-alkoxy-, cyano-C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-halogenoalkoxy-,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-a- lkoxy-,
carboxyl-C.sub.1-C.sub.4-alkoxy-, C.sub.1-C.sub.4-alkoxy-carbonyl--
C.sub.1-C.sub.4-alkoxy-,
C.sub.1-C.sub.4-alkylaminocarbonyl-C.sub.1-C.sub.- 4-alkoxy-,
di-(C.sub.1-C.sub.4-alkyl)-aminocarbonyl-C.sub.1-C.sub.4-alkoxy- -,
C.sub.1-C.sub.4-alkoxy-carbonyl-, C.sub.2-C.sub.4-alkenyloxy-,
C.sub.2-C.sub.4-alkinyloxy-, C.sub.1-C.sub.4-alkylthio-,
C.sub.1-C.sub.4-halogenoalkylthio-,
C.sub.1-C.sub.4-alkylsulphinyl-,
C.sub.1-C.sub.4-halogenoalkylsulphinyl-,
C.sub.1-C.sub.4-alkylsulphonyl-,
C.sub.1-C.sub.4-halogenoalkylsulphonyl-,
C.sub.1-C.sub.4-alkyl-carbonyl-a- mino-,
C.sub.1-C.sub.4-alkoxy-carbonyl-amino- or
C.sub.1-C.sub.4-alkyl-sul- phonyl-amino-substituted
nitrogen-containing heterocyclic grouping from the group consisting
of pyrrolyl, pyrazolyl, imidazolyl, triazolyl, triazolinyl,
pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl,
benzoxazolyl, benzothiazolyl, quinolinyl, quinazolinyl,
quinoxalinyl,
[0012] including all possible tautomeric forms of the compounds of
the general formula (I) and the possible salts and acid or base
adducts of the compounds of the general formula (I).
[0013] In the definitions, the hydrocarbon chains, such as alkyl or
alkanediyl, are in each case straight-chain or branched--including
in combination with heteroatoms, such as in alkoxy.
[0014] Preferred substituents or preferred ranges of the radicals
that are present in the formulae given above and below are defined
below.
[0015] Q preferably represents O (oxygen), S (sulphur) or
SO.sub.2.
[0016] R.sup.1 preferably represents hydrogen, amino, in each case
optionally cyano-, fluorine-, chlorine-, methoxy- or
ethoxy-substituted methyl, ethyl, n- or i-propyl, or in each case
optionally fluorine- and/or chlorine-substituted propenyl or
propinyl.
[0017] R.sup.2 preferably represents cyano, carboxyl, carbamoyl,
thiocarbamoyl or in each case optionally cyano-, fluorine-,
chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or
i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or
i-propoxycarbonyl.
[0018] R.sup.3 preferably represents hydrogen, fluorine, chlorine,
bromine or in each case optionally fluorine- and/or
chlorine-substituted methyl ethyl, n- or i-propyl.
[0019] R.sup.4 preferably represents hydrogen, cyano, fluorine,
chlorine or bromine.
[0020] R.sup.5 preferably represents cyano, thiocarbamoyl, bromine
or in each case optionally fluorine- and/or chlorine-substituted
methyl, ethyl, methoxy or ethoxy.
[0021] R.sup.6 preferably represents an in each case optionally
nitro-, hydroxyl-, amino-, cyano-, carboxyl-, carbamoyl-,
fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-,
n-, i-, s- or t-butyl-, chloromethyl-, fluoromethyl-,
dichloromethyl-, difluoromethyl-, trichloromethyl-,
trifluoromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-,
chloroethyl-, fluoroethyl-, dichloroethyl-, difluoroethyl,
chlorofluoroethyl-, trichloroethyl-, trifluoroethyl-,
chlorodifluoroethyl-, fluorodichloroethyl-, tetrafluoroethyl-,
chlorotrifluoroethyl-, pentafluoroethyl-, chloro-n-propyl-,
fluoro-n-propyl-, chloro-i-propyl-, fluoro-i-propyl-,
dichloropropyl-, difluoropropyl-, trichloropropyl-,
trifluoropropyl-, cyanomethyl-, cyanoethyl-, cyanopropyl-,
carboxymethyl-, carboxyethyl-, carboxypropyl-, methoxymethyl-,
ethoxymethyl-, propoxymethyl-, methoxyethyl-, ethoxyethyl-,
methoxycarbonylmethyl-, ethoxycarbonylmethyl-, n- or
i-propoxycarbonylmethyl-, methylaminocarbonylmethyl-,
ethylaminocarbonylmethyl-, dimethylaminocarbonylmethyl-,
methoxycarbonylethyl-, ethoxycarbonylethyl-, n- or
i-propoxycarbonylethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-,
i-, s- or t-butoxy-, difluoromethoxy-, trifluoromethoxy-,
chlorodifluoromethoxy-, carboxymethoxy-, carboxyethoxy-,
methoxycarbonylmethoxy-, ethoxycarbonylmethoxy-, n- or
i-propoxycarbonylmethoxy-, methylaminocarbonylmethoxy-,
ethylaminocarbonylmethoxy-, dimethylaminocarbonylmethoxy-,
methoxycarbonylethoxy-, ethoxycarbonylethoxy-, n- or
i-propoxycarbonylethoxy-, methylaminocarbonylethoxy-,
ethylaminocarbonylethoxy-, dimethylaminocarbonylethoxy-,
methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-,
propenyloxy-, butenyloxy-, propinyloxy-, butinyloxy-, methylthio-,
ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-,
difluoromethylthio-, trifluoromethylthio-,
chlorodifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, n- or
i-propylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-,
ethylsulphonyl-, n- or i-propylsulfonyl-,
trifluoromethylsulphonyl-, acetylamino-, propionylamino-, n- or
i-butyroylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, n-
or i-propoxycarbonylamino-, methylsulphonylamino-,
ethylsulphonylamino-, n- or i-propylsulphonylamino-substituted
nitrogen-containing heterocyclic grouping form the group consisting
of pyrrolyl, pyrazolyl, imidazolyl, triazolyl, triazolinyl,
pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl,
benzoxazolyl, benzothiazolyl, quinolinyl, quinazolinyl,
quinoxalinyl.
[0022] Q particularly preferably represents O (oxygen) or S
(sulphur).
[0023] R.sup.1 particularly preferably represents hydrogen, amino
or represents in each case optionally fluorine-, chlorine-,
methoxy- or ethoxy-substituted methyl or ethyl.
[0024] R.sup.2 particularly preferably represents cyano, carboxyl,
carbamoyl or in each case optionally fluorine- and/or
chlorine-substituted methyl, ethyl, methoxycarbonyl or
ethoxycarbonyl.
[0025] R.sup.3 particularly preferably represents hydrogen,
fluorine, chlorine, bromine or in each case optionally fluorine-
and/or chlorine-substituted methyl or ethyl.
[0026] R.sup.4 particularly preferably represents hydrogen,
fluorine or chlorine.
[0027] R.sup.5 particularly preferably represents cyano,
thiocarbamoyl, bromine or trifluoromethyl.
[0028] R.sup.6 particularly preferably represents an in each case
optionally nitro-, hydroxyl-, amino-, cyano-, carboxyl-,
carbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or
i-propyl-, n-, i-, s- or t-butyl-, dichloromethyl-,
difluoromethyl-, trichloromethyl-, trifluoromethyl-,
chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n-
or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-,
trifluoromethoxy-, chlorodifluoromethoxy-, carboxymethoxy-,
carboxyethoxy-, methoxycarbonylmethoxy-, ethoxycarbonylmethoxy-, n-
or i-propoxycarbonylmethoxy-, methoxycarbonylethoxy-,
ethoxycarbonylethoxy-, n- or i-propoxycarbonylethoxy-,
methoxycarbonyl-, ethoxycarbonyl-, propenyloxy-, butenyloxy-,
propinyloxy-, butinyloxy-, methylthio-, ethylthio-, n- or
i-propylthio-, n-, i-, s- or t-butylthio-, difluoromethylthio-,
trifluoromethylthio-, chlorodifluorormethylthio-, methylsulphinyl-,
ethylsulphinyl-, n- or i-propylsulphinyl-,
trifluoromethylsulphinyl-, methylsulphonyl, ethylsulphonyl-, n- or
i-propylsulphonyl-, trifluoromethylsulphonyl-, acetylamino-,
propionylamino-, n- or i-butyroylamino-, methoxycarbonylamino-,
ethoxycarbonylamino-, n- or i-propoxycarbonylamino-,
methylsulphonylamino-, ethylsulphonylamino-, n- or
i-propylsulphonylamino-substituted nitrogen-containing heterocyclic
grouping from the group consisting of pyrrolyl, pyrazolyl,
imidazolyl, triazolyl, triazolinyl, pyridinyl, pyrazinyl,
pyridazinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl,
quinolinyl, quinazolinyl, quinoxalinyl.
[0029] Q very particularly preferably represents O (oxygen).
[0030] R.sup.1 very particularly preferably represents hydrogen,
amino, methyl or ethyl.
[0031] R.sup.2 very particularly preferably represents cyano or
trifluoromethyl.
[0032] R.sup.3 very particularly preferably represents hydrogen,
chlorine or methyl.
[0033] R.sup.5 very particularly preferably represents cyano,
thiocarbamoyl or bromine.
[0034] R.sup.6 very particularly preferably represents in each case
optionally hydroxyl-, amino-, cyano-, carboxyl-, carbamoyl-,
fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-,
n-, i-, s- or t-butyl-, dichloromethyl-, difluoromethyl-,
trichloromethyl-, trifluoromethyl-, chlorodifluoromethyl-,
fluorodichloromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,
difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-,
carboxymethoxy-, carboxyethoxy-, methoxycarbonylmethoxy-,
ethoxycarbonylmethoxy-, n- or i-propoxycarbonylmethoxy-,
methoxycarbonylethoxy-, ethoxycarbonylethoxy-, n- or
i-propoxycarbonylethoxy-, methoxycarbonyl-, ethoxycarbonyl-,
propenyloxy-, butenyloxy-, propinyloxy-, butinyloxy-, methylthio-,
ethylthio-, n- or i-propylthio-, difluoromethylthio-,
trifluoromethylthio-, chlorodifluoromethylthio-, methylsulphinyl-,
ethylsulphinyl-, n- or i-propylsulphinyl-,
trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or
i-propylsulfonyl-, trifluoromethylsulphonyl-, acetylamino-,
propionylamino-, n- or i-butyroylamino-, methoxycarbonylamino-,
ethoxycarbonylamino-, n- or i-propoxycarbonylamino-,
methylsulphonylamino-, ethylsulphonylamino-, n- or
i-propylsulphonylamino-substituted pyrazolyl, pyridinyl,
pyrimidinyl, triazinyl or benzoxazolyl.
[0035] R.sup.1 most preferably represents hydrogen, amino or
methyl.
[0036] R.sup.2 most preferably represents trifluoromethyl.
[0037] R.sup.5 most preferably represents cyano or bromine.
[0038] R.sup.6 most preferably represents in each case optionally
hydroxyl-, amino-, cyano-, fluorine-, chlorine-, methyl-, ethyl-,
trichloromethyl-, methoxy- or ethoxy-substituted pyrazolyl,
pyridinyl, pyrimidinyl or benzoxazolyl.
[0039] R.sup.6 represents, with extraordinary preference,
pyrimidinyl.
[0040] A very particularly preferred group are those compounds of
the formula (I) in which
[0041] Q represents O (oxygen),
[0042] R.sup.1 represents methyl,
[0043] R.sup.2 represents trifluoromethyl,
[0044] R.sup.3 represents hydrogen, chlorine or methyl,
[0045] R.sup.4 represents hydrogen, fluorine or chlorine,
[0046] R.sup.5 represents cyano and
[0047] R.sup.6 represents 1-methyl-pyrazol-5-yl,
1,3-dimethyl-pyrazol-5-yl- , 1,3,4-trimethyl-pyrazol-5-yl,
1-methyl-3-trifluoromethyl-pyrazol-5-yl, 1-ethyl-pyrazol-5-yl,
1-ethyl-3-methyl-pyrazol-5-yl,
1-ethyl-3-trifluoromethyl-pyrazol-5-yl, 1-n-propyl-pyrazol-5-yl,
1-n-propyl-3-methyl-pyrazol-5-yl,
1-n-propyl-3-trifluoromethyl-pyrazol-5-- yl,
1-1-propyl-pyrazol-5-yl, 1-1-propyl-3-methyl-pyrazol-5-yl,
1-1-propyl-3-trifluoromethyl-pyrazol-5-yl, 1-n-butyl-pyrazol-5-yl,
1-1-butyl-pyrazol-5-yl, 1-s-butyl-pyrazol-5-yl or
1-t-butyl-pyrazol-5-yl.
[0048] A further very particularly preferred group are those
compounds of the formula (I) in which
[0049] Q represents O (oxygen),
[0050] R.sup.1 represents methyl,
[0051] R.sup.2 represents trifluoromethyl,
[0052] R.sup.3 represents hydrogen, chlorine or methyl,
[0053] R.sup.4 represents hydrogen, fluorine or chlorine,
[0054] R.sup.5 represents bromine and
[0055] R.sup.6 represents 1-methyl-pyrazol-5-yl,
1,3-dimethyl-pyrazol-5-yl- , 1,3,4-trimethyl-pyrazol-5-yl,
1-methyl-3-trifluoromethyl-pyrazol-5-yl, 1-ethyl-pyrazol-5-yl,
1-ethyl-3-methyl-pyrazol-5-yl,
1-ethyl-3-trifluoromethyl-pyrazol-5-yl, 1-n-propyl-pyrazol-5-yl,
1-n-propyl-3-methyl-pyrazol-5-yl,
1-n-propyl-3-trifluoromethyl-pyrazol-5-- yl,
1-1-propyl-pyrazol-5-yl, 1-1-propyl-3-methyl-pyrazol-5-yl,
1-1-propyl-3-trifluoromethyl-pyrazol-5-yl, 1-n-butyl-pyrazol-5-yl,
1-1-butyl-pyrazol-5-yl, 1-s-butyl-pyrazol-5-yl or
1-t-butyl-pyrazol-5-yl.
[0056] A further very particularly preferred group are those
compounds of the formula (I) in which
[0057] Q represents O (oxygen),
[0058] R.sup.1 represents amino,
[0059] R.sup.2 represents trifluoromethyl,
[0060] R.sup.3 represents hydrogen, chlorine or methyl,
[0061] R.sup.4 represents hydrogen, fluorine or chlorine,
[0062] R.sup.5 represents cyano and
[0063] R.sup.6 represents 1-methyl-pyrazol-5-yl,
1,3-dimethyl-pyrazol-5-yl- , 1,3,4-trimethyl-pyrazol-5-yl,
1-methyl-3-trifluoromethyl-pyrazol-5-yl, 1-ethyl-pyrazol-5-yl,
1-ethyl-3-methyl-pyrazol-5-yl,
1-ethyl-3-trifluoromethyl-pyrazol-5-yl, 1-n-propyl-pyrazol-5-yl,
1-n-propyl-3-methyl-pyrazol-5-yl,
1-n-propyl-3-trifluoromethyl-pyrazol-5-- yl,
1-1-propyl-pyrazol-5-yl, 1-1-propyl-3-methyl-pyrazol-5-yl,
1-1-propyl-3-trifluoromethyl-pyrazol-5-yl, 1-n-butyl-pyrazol-5-yl,
1-1-butyl-pyrazol-5-yl, 1-s-butyl-pyrazol-5-yl or
1-t-butyl-pyrazol-5-yl.
[0064] A further very particularly preferred group are those
compounds of the formula (I) in which
[0065] Q represents O (oxygen),
[0066] R.sup.1 represents amino,
[0067] R.sup.2 represents trifluoromethyl,
[0068] R.sup.3 represents hydrogen, chlorine or methyl,
[0069] R.sup.4 represents hydrogen, fluorine or chlorine,
[0070] R.sup.5 represents bromine and
[0071] R.sup.6 represents 1-methyl-pyrazol-5-yl,
1,3-dimethyl-pyrazol-5-yl- , 1,3,4-trimethyl-pyrazol-5-yl,
1-methyl-3-trifluoromethyl-pyrazol-5-yl, 1-ethyl-pyrazol-5-yl,
1-ethyl-3-methyl-pyrazol-5-yl,
1-ethyl-3-trifluoromethyl-pyrazol-5-yl, 1-n-propyl-pyrazol-5-yl,
1-n-propyl-3-methyl-pyrazol-5-yl,
1-n-propyl-3-trifluoromethyl-pyrazol-5-- yl,
1-1-propyl-pyrazol-5-yl, 1-1-propyl-3-methyl-pyrazol-5-yl,
1-1-propyl-3-trifluoromethyl-pyrazol-5-yl, 1-n-butyl-pyrazol-5-yl,
1-1-butyl-pyrazol-5-yl, 1-s-butyl-pyrazol-5-yl or
1-t-butyl-pyrazol-5-yl.
[0072] A further very particularly preferred group are those
compounds of the formula (I) in which
[0073] Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the
meanings given above and
[0074] R.sup.6 represents pyrimidin-2-yl, 5-chloro-pyrimidin-2-yl,
5-fluoro-pyrimidin-2-yl, 4,5-dichloro-pyrimidin-2-yl,
4,5-difluoro-pyrimidin-2-yl, 4-chloro-5-fluoro-pyrimidin-2-yl,
4-methyl-pyrimidin-2-yl, 4,6-dimethyl-pyrimidin-2-yl,
4-methyl-6-trifluoromethyl-pyrimidin-2-yl,
5-chloro-4,6-dimethyl-pyrimidi- n-2-yl,
5-fluoro-4,6-dimethyl-pyrimidin-2-yl, 4,5,6-trimethyl-pyrimidin-2--
yl, 4-methoxy-6-methyl-pyrimidin-2-yl,
6-difluoromethoxy-4-methyl-pyrimidi- n-2-yl,
4-methoxy-6-trifluoromethyl-pyrimidin-2-yl,
4,6-dimethoxy-pyrimidin-2-yl, pyrimidin-4-yl,
6-chloro-pyrimidin-4-yl, 5,6-dichloro-pyrimidin-4-yl,
6-chloro-5-fluoro-pyrimidin-4-yl, 6-methyl-pyrimidin-4-yl,
5-chloro-6-methyl-pyrimidin-4-yl, 6-trifluoromethyl-pyrimidin-4-yl,
6-hydroxy-pyrimidin-4-yl, 6-methoxy-pyrimidin-4-yl,
6-methoxycarbonylmethoxy-pyrimidin-4-yl,
6-ethoxycarbonylmethoxy-pyrimidin-4-yl,
6-methoxycarbonylethoxy-pyrimidin- -4-yl,
6-ethoxycarbonylethoxy-pyrimidin-4-yl,
6-chloro-5-fluoro-pyrimidin-- 4-yl, 5-fluoro-4-hydroxy-pyrimin-4-yl
or 5-fluoro-6-methoxy-pyrimidin-4-yl- .
[0075] A further very particularly preferred group are those
compounds of the formula (I) in which
[0076] Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the
meanings given above and
[0077] R.sup.6 represents pyridin-2-yl, pyridin-3-yl, pyridin-4-yl,
3-chloro-pyridin-2-yl, 3-fluoro-pyridin-2-yl,
4-chloro-pyridin-2-yl, 4-fluoro-pyridin-2-yl,
5-chloro-pyridin-2-yl, 5-fluoro-pyridin-2-yl,
3,4-dichloro-pyridin-2-yl, 3,5-dichloro-pyridin-2-yl,
3,6-dichloro-pyridin-2-yl, 3,4-difluoro-pyridin-2-yl,
3,5-di-fluoro-pyridin-2-yl, 3,6-difluoro-pyridin-2-yl,
0,3,5,6-trichloro-pyridin-2-yl, 3,5,6-trifluoro-pyridin-2-yl,
3-cyano-pyridin-2-yl, 4-cyano-pyridin-2-yl, 5-cyano-pyridin-2-yl,
6-cyano-pyridin-2-yl, 3-methyl-pyridin-2-yl, 4-methyl-pyridin-2-yl,
5-methyl-pyridin-2-yl, 6-methyl-pyridin-2-yl,
4-chloro-pyridin-3-yl, 4-fluoro-pyridin-3-yl,
5-chloro-pyridin-3-yl, 5-fluoro-pyridin-3-yl,
6-chloro-pyridin-3-yl, 6-fluoro-pyridin-3-yl,
4,5-dichloro-pyridin-3-yl, 4,5-difluoro-pyridin-3-yl,
2-cyano-pyridin-3-yl, 4-cyano-pyridin-3-yl, 5-cyano-pyridin-3-yl,
6-cyano-pyridin-3-yl, 2-methyl-pyridin-3-yl, 4-methyl-pyridin-3-yl,
5-methyl-pyridin-3-yl, 6-methyl-pyridin-3-yl,
2-chloro-pyridin-4-yl, 2-fluoro-pyridin-4-yl,
3-chloro-pyridin-4-yl, 3-fluoro-pyridin-4-yl, 2-cyano-pyridin-4-yl,
3-cyano-pyridin-4-yl, 2-methyl-pyridin-4-yl or
3-methyl-pyridin-4-yl.
[0078] A further very particularly preferred group are those
compounds of the formula (I) in which
[0079] Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the
meanings given above and
[0080] R.sup.6 represents pyrimidin-2-yl, 5-chloro-pyrimidin-2-yl,
5-fluoro-pyrimidin-2-yl, 4,5-dichloro-pyrimidin-2-yl,
4,5-difluoro-pyrimidin-2-yl, 4-chloro-5-fluoro-pyrimidin-2-yl,
4-methyl-pyrimidin-2-yl, 4,6-dimethyl-pyrimidin-2-yl,
4-methyl-6-trifluoromethyl-pyrimidin-2-yl,
5-chloro-4,6-dimethyl-pyrimidi- n-2-yl,
5-fluoro-4,6-dimethyl-pyrimidin-2-yl, 4,5,6-trimethyl-pyrimidin-2--
yl, 4-methoxy-6-methyl-pyrimidin-2-yl,
6-difluormethoxy-4-methyl-pyrimidin- -2-yl,
4-methoxy-6-trifluoromethyl-pyrimidin-2-yl,
4,6-dimethoxy-pyrimidin- -2-yl.
[0081] Preference according to the invention is given to those
compounds of the formula (I), which contain a combination of the
meanings listed above as being preferred.
[0082] Particular preference according to the invention is given to
those compounds of the formula (I) which contain a combination of
the meanings listed above as being particularly preferred.
[0083] Very particular preference according to the invention is
given to those compounds of the formula (I) which contain a
combination of the meanings listed above as being very particularly
preferred.
[0084] Most preference according to the invention is given to those
compounds of the formula (I) which contain a combination of the
meanings listed above as being most preferred.
[0085] The abovementioned general or preferred radical definitions
apply both to the end products of the formula (I) and,
correspondingly, to the starting materials or intermediates
required in each case for the preparation. These radical
definitions can be combined with one another as desired, i.e.
including combinations between the given preferred ranges.
[0086] The novel substituted phenyluracils of the general formula
(I) have interesting biological properties. In particular, they
have strong herbicidal activity.
[0087] The novel substituted phenyluracils of the general formula
(I) are obtained when
[0088] (a) phenyluracils of the general formula (II) 3
[0089] in which
[0090] Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each
as defined above
[0091] are reacted with compounds of the general formula (III)
X.sup.1--R.sup.6 (III)
[0092] in which
[0093] R.sup.6 is as defined above and
[0094] X.sup.1 represents halogen or alkylsulphonyl,
[0095] if appropriate in the presence of a reaction auxiliary and
if appropriate in the presence of a diluent,
[0096] or when
[0097] (b) halogenophenyluracils of the general formula (IV) 4
[0098] in which
[0099] R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each as
defined above and
[0100] X.sup.2 represents halogen,
[0101] are reacted with compounds of the general formula (V)
M-Q-R.sup.6 (V)
[0102] in which
[0103] Q and R.sup.6 are each as defined above and
[0104] M represents hydrogen or a metal equivalent,
[0105] if appropriate in the presence of a reaction auxiliary and
if appropriate in the presence of a diluent,
[0106] or when
[0107] (c) aminoalkenoic acid esters of the general formula (VI)
5
[0108] in which
[0109] R.sup.1, R.sup.2 and R.sup.3 are each as defined above
and
[0110] R represents alkyl, aryl or arylalkyl,
[0111] are reacted with substituted phenyl isocyanates of the
general formula (VII) 6
[0112] in which
[0113] Q, R.sup.4, R.sup.5 and R.sup.6 are each as defined
above
[0114] or with substituted phenylurethanes (phenylcarbamates) of
the general formula (VIII) 7
[0115] in which
[0116] Q, R.sup.4, R.sup.5 and R.sup.6 are each as defined above
and
[0117] R represents alkyl, aryl or arylalkyl,
[0118] if appropriate in the presence of a reaction auxiliary and
if appropriate in the presence of a diluent,
[0119] or when
[0120] (d) substituted N-phenyl-1-alkoxycarbonylamino-maleimides of
the general formula (IX) 8
[0121] in which
[0122] Q, R.sup.4, R.sup.5 and R.sup.6 are each as defined above
and
[0123] R' represents alkyl
[0124] are reacted with a metal hydroxide in the presence of water
and, if appropriate in the presence of an organic solvent,
[0125] or when
[0126] (e) substituted phenyluracils of the general formula (Ia)
9
[0127] in which
[0128] Q, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each
as defined above
[0129] are reacted with 1-aminooxy-2,4-dinitro-benzene or
2-aminooxysulphonyl-1,3,5-trimethylbenzene or with alkylating
agents of the general formula (X)
X.sup.3-A.sup.1 (X)
[0130] in which
[0131] A.sup.1 represents optionally cyano-, halogen- or
C.sub.1-C.sub.4-alkoxy-substituted alkyl having 1 to 4 carbon atoms
or in each case optionally halogen-substituted alkenyl or alkinyl
having in each case 2 to 4 carbon atoms, and
[0132] X.sup.3 represents halogen or the grouping
--O--SO.sub.2--O-A.sup.1- ,
[0133] if appropriate in the presence of a reaction auxiliary and
if appropriate in the presence of a diluent,
[0134] and electrophilic or nucleophilic and/or oxidation or
reduction reactions within the scope of the definition of the
substituents are, if appropriate, subsequently carried out in a
customary manner.
[0135] The compounds of the general formula (I) can be converted by
customary methods into other compounds of the general formula (I)
in accordance with the above definition, for example by reaction
with dicyanogen or hydrogen sulphide (for example
R.sup.5:Br.fwdarw.CN, CN.fwdarw.CSNH.sub.2, cf. the Preparation
Examples).
[0136] Using, for example,
3-amino-1-(2-chloro-4-bromo-5-hydroxy-phenyl)-4-
-trifluoromethyl-3,6-dihydro-2,6-dioxo-1 (2H)-pyrimidine and
4-difluoromethoxy-6-methyl-2-methylsulphonyl-pyrimidine as starting
materials, the course of the reaction in the process (a) according
to the invention can be illustrated by the following formula
scheme: 10
[0137] Using, for example,
1-(4-cyano-2,5-difluoro-phenyl)-4-chlorodifluor-
methyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine and
5-hydroxy-1-methyl-pyraz- ole as starting materials, the course of
the reaction in the process (b) according to the invention can be
illustrated by the following formula scheme: 11
[0138] Using, for example, methyl 3-amino-4,4,4-trifluoro-crotonate
and 4-bromo-2-chloro-5-(5-chloro-pyrimidin-2-yl-thio)-phenyl
isocyanate as starting materials, the course of the reaction in the
process (c) according to the invention can be illustrated by the
following formula scheme: 12
[0139] Using, for example, methyl
[1-[4-cyano-2-fluoro-5-(pyrimidin-2-yl)--
phenyl]-2,5-dioxo-2,5-dihydro-11H-pyrrol-3-yl]-carbamate as
starting material, the course of the reaction in the process (d)
according to the invention can be illustrated by the following
formula scheme: 13
[0140] Using, for example,
1-[4-cyano-2-fluoro-5-(1,3-dimethyl-pyrazol-5-y-
l-oxy)-phenyl]-4-difluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine
and methyl bromide as starting materials, the course of the
reaction in the process (e) according to the invention can be
illustrated by the following formula scheme: 14
[0141] The formula (II) provides a general definition of the
phenyluracils to be used as starting materials in the process (a)
according to the invention for preparing compounds of the formula
(a). In the formula (II), Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and
R.sup.5 each preferably or in particular have those meanings which
have already mentioned above, in connection with the description of
the compounds of the formula (I) according to the invention, as
being preferred or as being particularly preferred for Q, R.sup.1,
R.sup.2, R.sup.3, R.sup.4 and R.sup.5.
[0142] The starting materials of the general formula (II) are known
and/or can be prepared by processes known per se (cf.
WO-A-97/01541, WO-A-98/54155).
[0143] The formula (III) provides a general definition of the
compounds further to be used as starting materials in the process
according to the invention. In the general formula (III), R.sup.6
preferably has that meaning which has already been mentioned above,
in connection with the description of the compounds of the general
formula (I) according to the invention, as being preferred,
particularly preferred, very particularly preferred or most
preferred for R.sup.6; X.sup.1 preferably represents fluorine,
chlorine, bromine, iodine or alkylsulphonyl having 1 to 3 carbon
atoms, in particular fluorine, chlorine, bromine or
methylsulphonyl.
[0144] Most of the starting materials of the general formula (III)
are known organic chemicals for synthesis.
[0145] The formula (IV) provides a general definition of the
halogenophenyluracils to be used as starting materials in the
process (d) according to the invention for preparing compounds of
the general formula (I). In the general formula (IV), R.sup.1,
R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each preferably have those
meanings which have already been mentioned above, in connection
with the description of the compounds of the general formula (I)
according to the invention, as being preferred, particularly
preferred, very particularly preferred or most preferred for
R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5; X.sup.2 preferably
represents fluorine, chlorine or bromine, in particular fluorine or
chlorine.
[0146] The starting materials of the general formula (IV) are known
and/or can be prepared by processes known per se (cf.
EP-A-648749).
[0147] The formula (V) provides a general definition of the
compounds further to be used as starting materials in the process
(b) according to the invention. In the general formula (V), Q and
R.sup.6 each preferably have those meanings which have already been
mentioned above, in connection with the description of the
compounds of the general formula (I) according to the invention, as
being preferred, particularly preferred, very particularly
preferred or most preferred for Q and R.sup.6; M preferably
represents hydrogen or an alkali metal, in particular hydrogen,
sodium or potassium.
[0148] Most of the starting materials of the general formula (V)
are known organic chemicals for synthesis.
[0149] The formula (VI) provides a general definition of the
aminoalkenoic acid esters to be used as starting materials in the
process (c) according to the invention for preparing compounds of
the general formula (I). In the general formula (VI), R.sup.1,
R.sup.2 and R.sup.3 each preferably have those meanings which have
already been mentioned above, in connection with the description of
the compounds of the general formula (I) according to the
invention, as being preferred, particularly preferred, very
particularly preferred or most preferred for R.sup.1, R.sup.2 and
R.sup.3; R preferably represents C.sub.1-C.sub.4-alkyl, phenyl or
benzyl, in particular methyl or ethyl.
[0150] The starting materials of the general formula (VI) are known
and/or can be prepared by processes known per se (cf. J.
Heterocycl. Chem. 9 (1972), 513-522).
[0151] The formula (VII) provides general definition of the phenyl
isocyanates further to be used as starting materials in process (c)
according to the invention and the formula (VIII) provides a
general definition of the phenylurethanes to be used alternatively.
In the general formulae (VII) and (VIII), Q, R.sup.4, R.sup.5 and
R.sup.6 each preferably have those meanings which have already been
mentioned above, in connection with the description of the
compounds of the general formula (I) according to the invention, as
being preferred, particularly preferred, very particularly
preferred or most preferred for Q, R.sup.4, R.sup.5 and R.sup.6; R
preferably represents C.sub.1-C.sub.4-alkyl, phenyl or benzyl, in
particular methyl, ethyl, phenyl or benzyl.
[0152] The starting materials of the general formulae (VII) and
(VIII) have hitherto not been disclosed in the literature; as novel
substances, they also form part of the subject-matter of the
present application.
[0153] The novel substituted phenyl isocyanates of the general
formula (VII) are obtained when aniline derivatives of the general
formula (XI) 15
[0154] in which
[0155] Q, R.sup.4, R.sup.5 and R.sup.6 are each as defined
above
[0156] are reacted with phosgene in the presence of a diluent, such
as, for example, chlorobenzene, at temperatures between -20.degree.
C. and +150.degree. C. (cf. also EP-A-648749).
[0157] The novel substituted phenylurethanes of the general formula
(VIII) are obtained when aniline derivatives of the general formula
(XI) 16
[0158] in which
[0159] Q, R.sup.4, R.sup.5 and R.sup.6 are each as defined
above
[0160] are reacted with chlorocarbonyl compounds of the general
formula (XII)
RO--CO--Cl (XII)
[0161] in which
[0162] R is as defined above,
[0163] if appropriate in the presence of an acid acceptor, such as,
for example, pyridine, and if appropriate in the presence of a
diluent, such as, for example, methylene chloride, at temperatures
between -20.degree. C. and +100.degree. C. (cf. the Preparation
Examples).
[0164] The aniline derivatives of the general formula (XI) required
as precursors are generally known and/or can be prepared by
processes known per se (cf. DE-A-3240975, DE-A-3337828,
EP-A-79311).
[0165] Hitherto undisclosed and, as novel substances, part of the
subject-matter of the present application are aniline derivatives
of the general formula (XIa) 17
[0166] in which
[0167] Q, R.sup.4 and R.sup.6 are each as defined above and
[0168] Y represents cyano, thiocarbamoyl or trifluoromethyl.
[0169] The novel aniline derivatives of the general formula (XIa)
are obtained when
[0170] (.alpha.) anilines of the general formula (XIII) 18
[0171] in which
[0172] Q, R.sup.4 and Y are each as defined above
[0173] are reacted with compounds of the general formula (III)
X.sup.1--R.sup.6 (III)
[0174] in which
[0175] R.sup.6 and X.sup.1 are each as defined above,
[0176] if appropriate in the presence of an acid acceptor, such as,
for example, potassium hydroxide, potassium carbonate or pyridine,
and if appropriate in the presence of a diluent, such as, for
example, methanol, acetonitrile, N,N-dimethyl-formamide or
N-methyl-pyrrolidone, at temperatures between 0.degree. C. and
200.degree. C. (cf. the Preparation Examples),
[0177] or when
[0178] (.beta.) anilines of the general formula (XIV) 19
[0179] in which
[0180] R.sup.4, X.sup.2 and Y are each as defined above
[0181] are reacted with compounds of the general formula (V)
M-Q-R.sup.6 (V)
[0182] in which
[0183] M, Q and R.sup.6 are each as defined above,
[0184] if appropriate in the presence of an acid acceptor, such as,
for example, potassium carbonate or sodium hydride, and if
appropriate in the presence of a diluent, such as, for example,
acetonitrile, N,N-dimethyl-formamide or N-methyl-pyrrolidone, at
temperatures between 0.degree. C. and 200.degree. C. (cf. the
Preparation Examples).
[0185] The formula (IX) provides a general definition of the
substituted N-phenyl-1-alkoxycarbonylamino-maleimides to be used as
starting materials in the process (d) according to the invention
for preparing compounds of the general formula (I). In the general
formula (IX), Q, R.sup.4, R.sup.5 and R.sup.6 each preferably have
those meanings which have already been mentioned above, in
connection with the description of the compounds of the general
formula (I) according to the invention, as being preferred,
particularly preferred, very particularly preferred or most
preferred for Q, R.sup.4, R.sup.5 and R.sup.6; R' preferably
represents C.sub.1-C.sub.4-alkyl, in particular methyl or
ethyl.
[0186] The novel substituted
N-phenyl-1-alkoxycarbonylamino-maleimides of the general formula
(IX) are obtained when alkyl (2,5-dioxo-2,5-dihydro-f-
uran-3-yl)-carbamates of the general formula (XV) 20
[0187] in which
[0188] R.sup.3 is as defined above and
[0189] R' represents alkyl (in particular methyl or ethyl)
[0190] are reacted with aniline derivatives of the general formula
(XI) 21
[0191] in which
[0192] Q, R.sup.4, R.sup.5 and R.sup.6 are each as defined
above,
[0193] if appropriate in the presence of a diluent, such as, for
example, acetic acid, at temperatures between 0.degree. C. and
200.degree. C.
[0194] The precursors of the general formula (XV) are known and/or
can be prepared by processes known per se (cf. DE-A-19604229).
[0195] The formula (Ia) provides a general definition of the
substituted phenyluracils to be used as starting materials in the
process (e) according to the invention for preparing compounds of
the general formula (I). In the general formula (Ia), Q, R.sup.2,
R.sup.3, R.sup.4, R.sup.5 and R.sup.6 each preferably or in
particular have those meanings which have already been mentioned
above, in connection with the description of the compounds of the
general formula (I) according to the invention, as being preferred
or as being particularly preferred for Q, R.sup.2, R.sup.3,
R.sup.4, R.sup.5 and R.sup.6.
[0196] As novel substances, the starting materials of the general
formula (Ia) for process (e) also form part of the subject-matter
of, the present application; they can be prepared by processes (a)
to (d) according to the invention.
[0197] The formula (X) provides a general definition of the
alkylating agents further to be used as starting materials in the
process (e) according to the invention. In the general formula (X),
A.sup.1 preferably represents in each case optionally cyano-,
fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl,
n- or i-propyl or in each case optionally fluorine- and/or
chlorine-substituted propenyl or propinyl, in particular methyl or
ethyl; X.sup.3 preferably represents chlorine, bromine, iodine,
methoxysulphonyloxy or ethoxysulphonyloxy, in particular bromine or
methoxysulphonyloxy.
[0198] The starting materials of the general formula (X) are known
organic chemicals for synthesis.
[0199] The processes according to the invention for preparing the
compounds of the general formula (I) are preferably carried out
using diluents. Suitable diluents for carrying out the processes
(a), (b), (c), (d) and (e) according to the invention are, in
addition to water, especially inert organic solvents. These
include, in particular, aliphatic, alicyclic or aromatic,
optionally halogenated hydrocarbons, such as, for example, benzine,
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 ether or
ethylene glycol diethyl ether; ketones, such as acetone, butanone
or methyl isobutyl ketone; nitriles, such as acetonitrile,
propionitrile or butyronitrile; amides, such as
N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide,
N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such
as methyl acetate or ethyl acetate, sulphoxides, such as dimethyl
sulphoxide, 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, mixtures thereof with water or pure water.
[0200] Suitable reaction auxiliaries for the processes (a), (b),
(c) and (e) according to the invention are, in general, the
customary inorganic or organic bases or acid acceptors. These
include preferably alkali metal or alkaline earth metal acetates,
amides, carbonates, bicarbonates, hydrides, hydroxides or
alkoxides, such as, for example, sodium acetate, potassium acetate
or calcium acetate, lithium amide, sodium amide, potassium amide or
calcium amide, sodium carbonate, potassium carbonate or calcium
carbonate, sodium bicarbonate, potassium bicarbonate or calcium
bicarbonate, lithium hydride, sodium hydride, potassium hydride or
calcium hydride, lithium hydroxide, sodium hydroxide, potassium
hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or
i-propoxide, n-, i-, s- or t-butoxide, or potassium methoxide,
ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore
also basic organic nitrogen compounds, such as, for example,
trimethylamine, triethylamine, tripropylamine, tributylamine,
ethyl-diisopropylamine, 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-dimethyl-amino-pyridi- ne, 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).
[0201] Other suitable reaction auxiliaries for the processes (a),
(b), (c) and (e) according to the invention are phase-transfer
catalysts. Examples of such catalysts which may be mentioned
are:
[0202] tetrabutylammonium bromide, tetrabutylammonium chloride,
tetraoctylammonium chloride, tetrabutylammonium hydrogen sulphate,
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-tributylammonium bromide, tetrabutylphosphonium
bromide, tetrabutylphosphonium chloride,
tributyl-hexadecylphosphonium bromide, butyl-triphenylphosphonium
chloride, ethyl-trioctylphosphonium bromide, tetraphenylphosphonium
bromide.
[0203] Preferred metal hydroxides used in the process (d) according
to the invention are alkali metal or alkaline earth metal
hydroxides, in particular lithium hydroxide, sodium hydroxide,
potassium hydroxide or calcium hydroxide.
[0204] When carrying out the processes (a), (b), (c), (d) and (e)
according to the invention, the reaction temperatures can be varied
within a relatively wide range. In general, the processes are
carried out at temperatures between 0.degree. C. and 150.degree.
C., preferably between 10.degree. C. and 120.degree. C.
[0205] The processes (a), (b), (c), (d) and (e) according to the
invention are generally carried out under atmospheric pressure.
However, it is also possible to carry out the processes according
to the invention under elevated or reduced pressure--in general
between 0.1 bar and 10 bar.
[0206] For carrying out the processes according to the invention,
the starting materials are generally employed in approximately
equimolar amounts. However, it is also possible to use a relatively
large excess of one of the components. 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. Work-up is carried out by
customary methods (cf. the Preparation Examples).
[0207] The active compounds according to the invention can be used
as defoliants, desiccants, haulm killers and, especially, as weed
killers. Weeds in the broadest sense are understood to mean all
plants which grow in locations where they are undesired. Whether
the substances according to the invention act as total or selective
herbicides depends essentially on the amount used.
[0208] The active compounds according to the invention can be used,
for example, in connection with the following plants:
[0209] Dicotyledonous weeds of the genera: Abutilon, Amaranthus,
Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens,
Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium,
Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia,
Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium,
Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo,
Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca,
Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio,
Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria,
Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,
Xanthium.
[0210] Dicotyledonous crops of the genera: Arachis, Beta, Brassica,
Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium,
Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum,
Solanum, Vicia.
[0211] Monocotyledonous weeds of the genera: Aegilops, Agropyron,
Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,
Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria,
Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca,
Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa,
Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa,
Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
[0212] Monocotyledonous crops of the genera: Allium, Ananas,
Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale,
Sorghum, Triticale, Triticum, Zea.
[0213] However, the use of the active compounds according to the
invention is in no way restricted to these genera, but also extends
in the same manner to other plants.
[0214] The active compounds according to the invention are
suitable, depending on the concentration, for the total control of
weeds, for example on industrial terrain and rail tracks, and on
paths and areas with and without tree plantings. Similarly, the
active compounds according to the invention can be employed for
controlling weeds in perennial crops, for example forests,
decorative tree plantings, orchards, vineyards, citrus groves, nut
orchards, banana plantations, coffee plantations, tea plantations,
rubber plantations, oil palm plantations, cocoa plantations, soft
fruit plantings and hop fields, on lawns, turf and pastureland, and
for the selective control of weeds in annual crops.
[0215] The compounds of the formula (I) according to the invention
have strong herbicidal activity and a broad activity spectrum when
used on the soil or on above-ground parts of plants. To a certain
extent, they are also suitable for the selective control of
monocotyledonous and dicotyledonous weeds in monocotyledonous and
dicotyledonous crops, both by the pre-emergence and by the
post-emergence method.
[0216] At certain concentrations or application rates, the active
compounds according to the invention can also be employed for
controlling animal pests and fungal or bacterial plant diseases. If
appropriate, they can also be used as intermediates or precursors
for the synthesis of other active compounds.
[0217] According to the invention, it is possible to treat all
plants and parts of plants. Plants are to be understood here as
meaning all plants and plant populations such as desired and
undesired wild plants or crop plants (including naturally occurring
crop plants). Crop plants can be plants which can be obtained by
conventional breeding and optimization methods or by
biotechnological and genetic engineering methods or combinations of
these methods, including the transgenic plants and including plant
cultivars which can or cannot be protected by plant breeders'
certificates. Parts of plants are to be understood as meaning all
above-ground and below-ground parts and organs of plants, such as
shoot, leaf, flower and root, examples which may be mentioned being
leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and
seeds and also roots, tubers and rhizomes. Parts of plants also
include harvested plants and vegetative and generative propagation
material, for example seedlings, tubers, rhizomes, cuttings and
seeds.
[0218] The treatment of the plants and parts of plants according to
the invention with the active compounds is carried out directly or
by action on their environment, habitat or storage area according
to customary treatment methods, for example by dipping, spraying,
evaporating, atomizing, broadcasting, brushing-on and, in the case
of propagation material, in particular in the case of seeds,
furthermore by one- or multi-layer coating.
[0219] The active compounds can be converted into the customary
formulations, such as solutions, emulsions, wettable powders,
suspensions, powders, dusts, pastes, soluble powders, granules,
suspo-emulsion concentrates, natural and synthetic substances
impregnated with active compound, and microencapsulations in
polymeric substances.
[0220] These formulations are produced in a known manner, for
example by mixing the active compounds with extenders, that is to
say liquid solvents and/or solid carriers, optionally with the use
of surfactants, that is to say emulsifiers and/or dispersants
and/or foam formers.
[0221] If the extender used is water, it is also possible to use,
for example, organic solvents as auxiliary solvents. Liquid
solvents which are mainly suitable are: aromatics, such as xylene,
toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated
aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or
methylene chloride, aliphatic hydrocarbons, such as cyclohexane or
paraffins, for example petroleum fractions, mineral and vegetable
oils, alcohols, such as butanol or glycol, and also their ethers
and esters, ketones, such as acetone, methyl ethyl ketone, methyl
isobutyl ketone or cyclohexanone, strongly polar solvents, such as
dimethylformamide and dimethyl sulphoxide, and water.
[0222] Suitable solid carriers are: for example ammonium salts and
round natural minerals, such as kaolins, clays, talc, chalk,
quartz, attapulgite, montmorillonite or diatomaceous earth, and
ground synthetic minerals, such as finely divided silica, alumina
and silicates; suitable solid carriers for granules are: for
example crushed and fractionated natural rocks, such as calcite,
marble, pumice, sepiolite, dolomite and synthetic granules of
inorganic and organic meals, and granules of organic material, such
as sawdust, coconut shells, maize cobs and tobacco stalks; suitable
emulsifiers and/or foam formers are: for example nonionic and
anionic emulsifiers, such as polyoxyethylene fatty acid esters,
polyoxyethylene fatty alcohol ethers, for example alkylaryl
polyglycol ethers, alkylsulphonates, alkyl sulphates,
arylsulphonates and protein hydrolysates; suitable dispersants are:
for example lignosulphite waste liquors and methylcellulose.
[0223] Tackifiers, such as carboxymethylcellulose, natural and
synthetic polymers in the form of powders, granules or latices,
such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and
also natural phospholipids, such as cephalins and lecithins, and
synthetic phospholipids can be used in the formulations. Other
possible additives are mineral and vegetable oils.
[0224] It is possible to use colorants, such as inorganic pigments,
for example iron oxide, titanium oxide, Prussian blue, and organic
dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal
phthalocyanine dyestuffs, and trace nutrients, such as salts of
iron, manganese, boron, copper, cobalt, molybdenum and zinc.
[0225] The formulations generally comprise between 0.1 and 95
percent by weight of active compound, preferably between 0.5 and
90%.
[0226] For controlling weeds, the active compounds according to the
invention, as such or in their formulations, can also be used as
mixtures with known herbicides and/or substances which improve the
compatibility with crop plants ("safeners"), finished formulations
or tank mixes being possible. Also possible are mixtures with
weed-killers comprising one or more known herbicides and a
safener.
[0227] Possible components for the mixtures are known herbicides,
for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor,
alloxydim (-sodium), ametryne, amicarbazone, amidochlor,
amidosulfuron, anilofos, asulam, atrazine, azafenidin,
azimsulfuron, beflubutamid, benazolin (-ethyl), benfuresate,
bensulfuron (-methyl), bentazon, benzfendizone, benzobicyclon,
benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac
(-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor,
butafenacil (-allyl), butroxydim, butylate, cafenstrole, caloxydim,
carbetamide, carfentrazone (-ethyl), chlomethoxyfen, chloramben,
chloridazon, chlorimuron (-ethyl), chlornitrofen, chlorsulfuron,
chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron,
clefoxydim, clethodim, clodinafop (-propargyl), clomazone,
clomeprop, clopyralid, clopyrasulfuron (-methyl), cloransulam
(-methyl), cumyluron, cyanazine, cybutryne, cycloate,
cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB,
desmedipham, diallate, dicamba, dichlorprop (-P), diclofop
(-methyl), diclosulam, diethatyl (-ethyl), difenzoquat,
diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,
dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,
diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb,
ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen,
ethoxysulfuron, etobenzanid, fenoxaprop (-P-ethyl), fentrazamide,
flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron,
florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone
(-sodium), flufenacet, flumetsulam, flumiclorac (-pentyl),
flumioxazin, flumipropyn, flumetsulam, fluometuron,
fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil,
flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone,
fluroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone,
fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron,
glufosinate (-ammonium), glyphosate (-isopropylammonium),
halosafen, haloxyfop (-ethoxyethyl, -P-methyl), hexazinone,
imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic,
imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron
(-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron,
isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen,
lenacil, linuron, MCPA, mecoprop, mefenacet, mesotrione,
metamitron, metazachlor, methabenzthiazuron, metobenzuron,
metobromuron, (alpha-)metolachlor, metosulam, metoxuron,
metribuzin, metsulfuron (-methyl), molinate, monolinuron,
naproanili de, napropamide, neburon, nicosulfuron, norflurazon,
orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,
oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid,
pendimethalin, pendralin, pentoxazone, phenmedipham, picolinafen,
piperophos, pretilachlor, primisulfuron (-methyl), profluazol,
prometryn, propachlor, propanil, propaquizafop, propisochlor,
propoxycarbazone (-sodium), propyzamide, prosulfocarb, prosulfuron,
pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron
(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate,
pyridatol, pyriftalid, pyriminobac (-methyl), pyrithiobac
(-sodium), quinchlorac, quinmerac, quinoclamine,
quizalofop(-P-ethyl, -P-tefuryl), rimsulfuron, sethoxydim,
simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron
(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron,
tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide,
thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb,
tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron
(-methyl), triclopyr, tridiphane, trifluralin, trifloxysulfuron,
triflusulfuron (-methyl), tritosulfuron.
[0228] A mixture with other known active compounds, such as
fungicides, insecticides, acaricides, nematicides, bird repellents,
plant nutrients and agents which improve soil structure, is also
possible.
[0229] 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 a
customary manner, for example by watering, spraying, atomizing or
broadcasting.
[0230] The active compounds according to the invention can be
applied both before and after emergence of the plants. They can
also be incorporated into the soil before sowing.
[0231] The amount of active compound used can vary within a
relatively wide range. It depends essentially on the nature of the
desired effect. In general, the amounts used are between 1 g and 10
kg of active compound per hectare of soil surface, preferably
between 5 g and 5 kg per ha.
[0232] The preparation and the use of the active compounds
according to the invention is illustrated by the examples
below.
PREPARATION EXAMPLES
Example 1
[0233] 22
[0234] (Process (c))
[0235] 1.03 g (5.6 mmol) of methyl
3-amino-4,4,4-trifluoro-crotonate are added to a mixture, cooled to
0.degree. C., of 0.28 g (7 mmol) of sodium hydride (60% strength
dispersion in mineral oil) in 10 ml of N,N-dimethyl-formamide. With
stirring, the mixture is allowed to warm to room temperature (about
20.degree. C.), and a solution of 2.0 g (5.62 mol) of O-ethyl
N-[4-bromo-2-fluoro-5-(pyrimidin-2-yl-oxy)-phenyl]-carbam- ate in
25 ml of N,N-dimethyl-formamide is then added dropwise. The
reaction mixture is heated at 150.degree. C. for 6 hours. The
mixture is then poured into 300 ml of 2N hydrochloric acid,
approximately the same volume of a 1:1 mixture of diethyl ether and
petroleum ether is added and the mixture is stirred for about 3
hours. The resulting crystalline product is isolated by filtration
with suction.
[0236] This gives 1.6 g (64% of theory) of
1-[4-bromo-2-fluoro-5-(pyrimidi-
n-2-yl-oxy)-phenyl]-4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1
(2H)-pyrimidine.
[0237] logP=1.96.sup.a)
Example 2
[0238] 23
[0239] (Process (e))
[0240] At room temperature, 0.46 g (3.6 mmol) of dimethyl sulphate
is added dropwise with stirring to a mixture of 1.35 g (3.0 mmol)
of
1-[4-bromo-2-fluoro-5-(pyrimidin-2-yl-oxy)-phenyl]-4-trifluormethyl-3,6-d-
ihydro-2,6-dioxo-1 (2H)-pyrimidine, 0.84 g (6.0 mmol) of potassium
carbonate and 25 ml of ace tonitrile, and the reaction mixture is
heated at reflux for 2 hours. The mixture is cooled to room
temperature, diluted with water to about twice its original volume
and then extracted three times with methylene chloride. The
combined organic phases are dried with sodium sulphate and
filtered. The filtrate is concentrated under waterpump vacuum and
the residue is taken up in ethyl acetate and filtered off with
suction through silica gel. The filtrate is concentrated under
waterpump vacuum, the residue is digested with diethyl ether and
the resulting crystalline product is isolated by filtration with
suction.
[0241] This gives 0.70 g (51% of theory) of
1-[4-bromo-2-fluoro-5-(pyrimid-
in-2-yl-oxy)-phenyl]-3-methyl-4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1
(2H)-pyrimidine.
[0242] logP=2.47.sup.a)
[0243] Analogously to Examples 1 and 2, and in accordance with the
general description of the preparation processes according to the
invention, it is also possible to prepare, for example, the
compounds of the general formula (I) listed in Table 1 below.
1TABLE 1 24 (I) Exxamples of compounds of the formula (I) Ex.
Physical No. Q R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 data
3 O CH.sub.3 CF.sub.3 H F CN 25 m.p.: 96.degree. C. 4 O CH.sub.3
CF.sub.3 H F CN 26 m.p.: 186.degree. C. 5 O CH.sub.3 CF.sub.3 H F
CN 27 m.p.: 143.degree. C. 6 O CH.sub.3 CF.sub.3 H F CN 28 logP =
2.59.sup.a) 7 O H CF.sub.3 H F CN 29 logP = 2.03.sup.a) 8 O
CH.sub.3 CF.sub.3 H F CN 30 logP = 2.50.sup.a) 9 O NH.sub.2
CF.sub.3 H F CN 31 logP '2 2.21.sup.a) 10 O H CF.sub.3 H F CN 32 11
O H CF.sub.3 H F CN 33 12 O NH.sub.2 CF.sub.3 H F CN 34 logP =
2.32.sup.a) 13 O H CF.sub.3 H F CN 35 .sup.1H-NMR (CD.sub.3CN,
.delta.): 7.75 ppm 14 O CH.sub.3 CF.sub.3 H F CN 36 m.p.:
182.degree. C. 15 O CH.sub.3 CF.sub.3 H F CN 37 m.p.: 92.degree. C.
16 O CH.sub.3 CF.sub.3 H F CN 38 17 O CH.sub.3 CF.sub.3 H F CN 39
18 O CH.sub.3 CF.sub.3 H F CN 40 19 O CH.sub.3 CF.sub.3 H F CN 41
20 O CH.sub.3 CF.sub.3 H F CN 42 logP = 3.08.sup.a) 21 O CH.sub.3
CF.sub.3 H F CN 43 22 O CH.sub.3 CF.sub.3 H F CN 44 23 O CH.sub.3
CF.sub.3 H F CN 45 24 O CH.sub.3 CF.sub.3 H F CN 46 25 O CH.sub.3
CF.sub.3 H F CN 47 26 O CH.sub.3 CF.sub.3 H F CN 48 logP =
3.26.sup.a) 27 O CH.sub.3 CF.sub.3 H F CN 49 28 O CH.sub.3 CF.sub.3
H F CN 50 29 O CH.sub.3 CF.sub.3 H F CN 51 30 O CH.sub.3 CF.sub.3 H
F CN 52 logP = 2.10.sup.a) 31 O CH.sub.3 CF.sub.3 H F CN 53 32 O
CH.sub.3 CF.sub.3 H F CN 54 33 O CH.sub.3 CF.sub.3 H F CN 55 34 O
CH.sub.3 CF.sub.3 H F CN 56 35 O CH.sub.3 CF.sub.3 H F CN 57 36 O
CH.sub.3 CF.sub.3 H F CN 58 37 O H CF.sub.3 H F CN 59 m.p.:
172.degree. C. 38 O NH.sub.2 CF.sub.3 H F CN 60 .sup.1H-NMR
(DMSO-D.sub.6, .delta.): 6.39 ppm 39 O CH.sub.3 CF.sub.3 H F CN 61
m.p.: 260.degree. C. 40 O NH.sub.2 CF.sub.3 H F Br 62 logP =
2.16.sup.a) 41 O CH.sub.3 CF.sub.3 H F CN 63 logP = 2.70.sup.a) 42
O H CF.sub.3 H F Br 64 43 O H CF.sub.3 H F Br 65 44 O CH.sub.3
CF.sub.3 H F Br 66 logP = 2.84.sup.a) 45 O CH.sub.3 CF.sub.3 H F Br
67 logP = 3.59.sup.a) 46 O CH.sub.3 CF.sub.3 H F Br 68 logP =
2.93.sup.a) 47 O CH.sub.3 CF.sub.3 H F Br 69 logP = 3.48.sup.a) 48
O CH.sub.3 CF.sub.3 H F Br 70 logP '2 3.83.sup.a) 49 O H CF.sub.3 H
F CN 71 50 O CH.sub.3 CF.sub.3 H F CN 72 logP '2 2.41.sup.a) 51 O H
CF.sub.3 H F CN 73 logP = 1.88.sup.a) 52 O H CF.sub.3 H F CN 74
logP = 2.16.sup.a) 53 O CH.sub.3 CF.sub.3 H F CN 75 logP =
2.33.sup.a) 54 O CH.sub.3 CF.sub.3 H F CN 76 logP = 2.68.sup.a) 55
O CH.sub.3 CF.sub.3 H F CN 77 logP = 3.26.sup.a) 56 O H CF.sub.3 H
F Br 78 57 O CH.sub.3 CF.sub.3 H F Br 79 logP = 3.16.sup.a) 58 O
CH.sub.3 CF.sub.3 H F Br 80 logP = 3.20.sup.a) 59 O H 81 H F CN 82
60 O CH.sub.3 83 H F CN 84 logP = 1.47.sup.a) 61 O H 85 H F CN 86
62 O H CF.sub.3 H F Br 87 63 O CH.sub.3 CN H F CN 88 logP =
2.11.sup.a) 64 O CH.sub.3 CF.sub.3 H F Br 89 logP = 2.96.sup.a) 65
O CH.sub.3 CF.sub.3 H F Br 90 logP = 3.20.sup.a) 66 O H CF.sub.3 H
F Br 91 67 O NH.sub.2 CF.sub.3 H F CN 92 68 O CH.sub.3 CF.sub.3 H H
CN 93 69 O CH.sub.3 CF.sub.3 H F CN 94 70 O CH.sub.3 CF.sub.3 H F
CN 95 71 O CH.sub.3 CF.sub.3 H F CN 96 72 O CH.sub.3 CF.sub.3 H F
CN 97 73 O CH.sub.3 CF.sub.3 H F CN 98
[0244] 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) using a reversed-phase column (C
18). Temperature: 43.degree. C.
[0245] (a) Mobile phases for the determination in the acidic range:
0.1% aqueous phosphoric acid, acetonitrile; linear gradient from
10% acetonitrile to 90% acetonitrile--the corresponding test
results in Table 1 are labelled .sup.a).
[0246] (b) Mobile phases for the determination in the neutral
range: 0.01 molar aqueous phosphate buffer solution, acetonitrile;
linear gradient from 10% acetonitrile to 90% acetonitrile--the
corresponding test results in Table 1 are labelled .sup.b).
[0247] Calibration was carried out using unbranched alkan-2-ones
(having 3 to 16 carbon atoms) with known logP values (determination
of the logP values by the retention times using linear
interpolation between two successive alkanones).
[0248] The lambda-max values were determined using the TV spectra
from 200 nm to 400 nm in the maxima of the chromatographic
signals.
[0249] The compound listed above in Table 1 as Example 4 can be
prepared, for example, as follows:
Example 4
[0250] 99
[0251] (Process (a))
[0252] A mixture of 0.50 g (1.5 mmol) of
1-(4-cyano-2-fluoro-5-hydroxy-phe-
nyl)-3-methyl-4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine,
0.30 g (2.2 mmol) of potassium carbonate and 50 ml of dimethyl
sulphoxide is stirred at room temperature (about 20.degree. C.) for
15 minutes. 0.36 g (1.7 mmol) of
4,6-dimethoxy-2-methylsulphonyl-pyrimidine is added, and the
reaction mixture is then stirred at 60.degree. C. for 3 hours, then
at 90.degree. C. for 8 hours, at room temperature for a further 12
hours, at 90.degree. C. for a further 12 hours and finally at room
temperature for a further 12 hours. The mixture is then poured into
a saturated aqueous solution of sodium chloride and extracted with
ethyl acetate, and the organic phase is washed with water and then
with saturated aqueous sodium chloride solution, dried with sodium
sulphate and filtered. The filtrate is concentrated under waterpump
vacuum, the residue is digested with diethyl ethyl/diisopropyl
ether and the resulting crystalline product is isolated by
filtration with suction.
[0253] This gives 0.20 g (29% of theory) of
1-[4-cyano-2-fluoro-5-(4,6-dim-
ethoxy-pyrimidin-2-yl-oxy)-phenyl]-3-methyl-4-trifluoromethyl-3,6-dihydro--
2,6-dioxo-1 (2H)-pyrimidine of melting point 186.degree. C.
[0254] Starting Materials of the Formula (VII):
Example (VIII-1)
[0255] 100
[0256] 2.0 g (7.0 mmol) of
4-bromo-2-fluoro-5-(pyrimidin-2-yl-oxy)-aniline are initially
charged in 25 ml of methylene chloride and, at room temperature
(about 20.degree. C.), admixed with 0.92 g (8.4 mmol) of ethyl
chloroformate and then with 0.67 g (8.4 mmol) of pyridine. The
reaction mixture is then stirred at room temperature for 4 hours.
The mixture is subsequently diluted with 2N hydrochloric acid to
about twice its original volume and extracted with methylene
chloride. The organic phase is dried with sodium sulphate and
filtered. The filtrate is concentrated under waterpump vacuum, the
residue is digested with diethyl ether and the resulting
crystalline product is isolated by filtration with suction.
[0257] This gives 2.2 g (89% of theory) of O-ethyl
N-[4-bromo-2-fluoro-5-(- pyrimidin-2-yl-oxy)-phenyl]-carbamate of
melting point 178.degree. C.
[0258] Analogously to Example (VIII-1), it is also possible to
prepare, for example, the compounds of the general formula (VIII)
listed in Table 2 below.
2TABLE 2 (VIII) 101 Examples of compounds of the formula (VIII) Ex.
No. Q R.sup.4 R.sup.5 R.sup.6 R Physical data VIII-2 O F CN 102
C.sub.2H.sub.5 logP = 2.19.sup.a) VIII-3 O F Br 103 C.sub.2H.sub.5
VIII-4 O F CN 104 C.sub.2H.sub.5 VIII-5 O F CN 105 C.sub.2H.sub.5
m.p.: 158.degree. C. VIII-6 O F CN 106 C.sub.2H.sub.5 VIII-7 O F CN
107 C.sub.2H.sub.5 VIII-8 O F CN 108 C.sub.2H.sub.5 VIII-9 O F CN
109 C.sub.2H.sub.5 VIII-10 O F CN 110 C.sub.2H.sub.5 VIII-11 O F CN
111 C.sub.2H.sub.5 VIII-12 O F CN 112 C.sub.2H.sub.5 VIII-13 O F CN
113 C.sub.2H.sub.5 VIII-14 O F CN 114 C.sub.2H.sub.5 VIII-15 O F CN
115 C.sub.2H.sub.5 VIII-16 O F CN 116 C.sub.2H.sub.5
USE EXAMPLES
Example A
[0259]
3 Pre-emergence test Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
[0260] 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.
[0261] Seeds of the test plants are sown in normal soil. After 24
hours, the soil is sprayed with the preparation of active compound
such that the particular amount of active compound desired is
applied per unit area. The concentration of active compound in the
spray liquor is chosen such that the particular amount of active
compound desired is applied in 1000 litres of water per
hectare.
[0262] After three weeks, the degree of damage to the plants is
rated in % damage in comparison to the development of the untreated
control. The figures denote:
4 0% = no effect (like untreated control) 100% = total
destruction
[0263] In this test, for example, the compounds of Preparation
Examples 2 and 6 exhibit very strong activity against weeds.
Example B
[0264]
5 Post-emergence test Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
[0265] 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.
[0266] Test plants of a height of 5-15 cm are sprayed with the
preparation of active compound such that the particular amounts of
active compound desired are applied per unit area. The
concentration of the spray liquor is chosen such that the
particular amounts of active compound desired are applied in 1000 l
of water/ha.
[0267] After three weeks, the degree of damage to the plants is
rated in % damage in comparison to the development of the untreated
control.
[0268] The figures denote:
6 0% = no effect (like untreated control) 100% = total
destruction
[0269] In this test, for example, the compounds of Preparation
Examples 2 and 6 exhibit very strong activity against weeds.
* * * * *