U.S. patent application number 09/906932 was filed with the patent office on 2002-08-22 for substituted 2-amino-1,3,5-triazines, their preparation, and their use as herbicides and plant growth regulators.
Invention is credited to Auler, Thomas, Bieringer, Hermann, Giencke, Wolfgang, Menne, Hubert, Willms, Lothar.
Application Number | 20020115567 09/906932 |
Document ID | / |
Family ID | 7649420 |
Filed Date | 2002-08-22 |
United States Patent
Application |
20020115567 |
Kind Code |
A1 |
Giencke, Wolfgang ; et
al. |
August 22, 2002 |
Substituted 2-amino-1,3,5-triazines, their preparation, and their
use as herbicides and plant growth regulators
Abstract
Substituted 2-amino-1,3,5-triazines, their preparation and their
use as herbicides and plant growth regulators The compounds of the
formula (I) and their salts 1 where the radicals R.sup.1 to
R.sup.4, A.sup.1, A.sup.2, L.sup.0, X and n are as defined in claim
1 are suitable as herbicides and plant growth regulators and can be
prepared by processes as claimed in claim 6.
Inventors: |
Giencke, Wolfgang; (Hofheim,
DE) ; Willms, Lothar; (Hofheim, DE) ; Auler,
Thomas; (Bad Soden, DE) ; Bieringer, Hermann;
(Eppstein, DE) ; Menne, Hubert; (Hofheim,
DE) |
Correspondence
Address: |
William F. Lawrence, Esq.
c/o FROMMER, LAWRENCE & HAUG LLP
745 Fifth Avenue
New York
NY
10151
US
|
Family ID: |
7649420 |
Appl. No.: |
09/906932 |
Filed: |
July 17, 2001 |
Current U.S.
Class: |
504/231 ;
544/194 |
Current CPC
Class: |
C07D 403/12 20130101;
A01N 43/68 20130101; C07D 251/18 20130101 |
Class at
Publication: |
504/231 ;
544/194 |
International
Class: |
A01N 043/66; C07D
251/40 |
Foreign Application Data
Date |
Code |
Application Number |
Jul 19, 2000 |
DE |
100 35 038.0 |
Claims
1. A compound of the formula (I) or a salt thereof 38in which
R.sup.1 is aryl, aryloxy, arylthio, arylamino,
N-aryl-N-(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.9)cycloalkyl,
(C.sub.3-C.sub.9)cycloalkyloxy, (C.sub.3-C.sub.9)cycloalkylthio,
(C.sub.3-C.sub.9)cycloalkylamino,
N-(C.sub.3-C.sub.9)cycloalkyl-N-(C.sub.1-C.sub.4)alkylamino,
di-[(C.sub.3-C.sub.9)cycloalkyl]amino, heterocyclyl,
heterocyclyloxy, heterocyclylthio, heterocyclylamino or
N-heterocyclyl-N-(C.sub.1-C.sub.4)- alkylamino, where each of the
last-mentioned 16 radicals is unsubstituted or substituted, or is
hydrogen, (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkynyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.2-C.sub.6)alkenyloxy, (C.sub.2-C.sub.6)alkynyloxy,
(C.sub.1-C.sub.6)alkylthio, (C.sub.2-C.sub.6)alkenylthio,
(C.sub.2-C.sub.6)alkynylthio, (C.sub.1-C.sub.6)alkylamino or
di-[(C.sub.1-C.sub.6)alkyl]amino, where each of the last-mentioned
11 radicals can be unsubstituted or substituted by one or more
radicals selected from the group consisting of halogen, hydroxyl,
cyano, nitro, thiocyanato, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.2-C.sub.4)alkenyloxy,
(C.sub.2-C.sub.4)haloalkenyloxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl,
(C.sub.1-C.sub.4)haloalkylthio, (C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, phenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, and radicals of the formulae R'-C(=Z')-,
R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-, R'-Z-C(=Z')-O-,
R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and R'R"N--C(=Z')-NR'"-, where
R', R" and R'" in each case independently of one another are
hydrogen (C.sub.1-C.sub.6)alkyl, aryl, aryl-(C.sub.1-C.sub.6)alkyl,
(C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted, and
where Z and Z' independently of one another are in each case an
oxygen or sulfur atom, R.sup.2 is (C.sub.3-C.sub.9)cycloalkyl which
is unsubstituted or substituted, (C.sub.4-C.sub.9)cycloalkenyl
which is unsubstituted or substituted, heterocyclyl which is
unsubstituted or substituted, or phenyl which is unsubstituted or
substituted, 39in which L.sup.1 is a direct bond, -O-, -S- or a
group of the formula -NG.sup.2-, U.sup.1, U.sup.2 independently of
one another are a group of the formula G.sup.3, OG.sup.4, SG.sup.5,
NG.sup.6G.sup.7, NG.sup.8NG.sup.9G.sup.10, NG.sup.11OG.sup.12 or
NG.sup.11SG.sup.12, U.sup.3 is a group of the formula G.sup.13,
OG.sup.14, SG.sup.15, NG.sup.16G.sup.17,
NG.sup.18NG.sup.19G.sup.20, NG.sup.21OG.sup.22 or
NG.sup.23SG.sup.24, U.sup.4 is a group of the formula G.sup.25,
OG.sup.26, SG.sup.27 or NG.sup.28G.sup.29, where the radicals
G.sup.1 to G.sup.29 independently of one another are hydrogen, aryl
which is unsubstituted or substituted or
(C.sub.3-C.sub.9)cycloalkyl which is unsubstituted or substituted,
or heterocyclyl which is substituted or unsubstituted, or are
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl or
(C.sub.2-C.sub.6)alkynyl, where each of the last-mentioned 3
radicals is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, cyano,
nitro, thiocyanato, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.2-C.sub.4)alkenyloxy,
(C.sub.2-C.sub.4)haloalkenyloxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl,
(C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, phenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, and radicals of the formulae R'-C(=Z')-,
R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-, R'-Z-C(=Z')-O-,
R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and R'R"N--C(=Z')-NR'"-, where
R', R" and R'" in each case independently of one another are
hydrogen, (C.sub.1-C.sub.6)alkyl, aryl,
aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and
where Z and Z' independently of one another are in each case an
oxygen or sulfur atom, and, inclusive of substituents, preferably
has 1 to 30 carbon atoms, or the radicals U.sup.1 and U.sup.3 or
U.sup.2 and U.sup.4 or U.sup.2 and G.sup.1 or U.sup.4 and G.sup.1,
as a pair, together with the atoms linking them are in each case a
carbocyclic or heterocyclic ring having 4 to 7 ring atoms, the ring
being unsubstituted or substituted, R.sup.4 is a radical of the
formula --B.sup.1-D.sup.1, where B.sup.1 and D.sup.1 are as defined
hereinbelow, A.sup.1 is a direct bond or straight-chain alkylene
having 1 to 5 carbon atoms or straight-chain alkenylene or
alkynylene having in each case 2 to 5 carbon atoms, where each of
the three last-mentioned diradicals is unsubstituted or substituted
by one or more radicals selected from the group consisting of
halogen, nitro, cyano, thiocyanato and radicals of the formula
-B.sup.2-D.sup.2, where B.sup.2 and D.sup.2 are as defined
hereinbelow, A.sup.2 is a direct bond or straight-chain alkylene
having 1 to 4 carbon atoms or straight-chain alkenylene or
alkynylene having in each case 2 to 5 carbon atoms, where each of
the three last-mentioned diradicals is unsubstituted or substituted
by one or more radicals selected from the group consisting of
halogen, nitro, cyano, thiocyanato and radicals of the formula
-B.sup.3-D.sup.3, or a divalent radical of the formula V.sup.1,
V.sup.2, V.sup.3, V.sup.4 or V.sup.5,-CR.sup.aR.sup.b-W*-CR.sup.-
cR.sup.d-
(V.sup.1)-CR.sup.aR.sup.b-W*-CR.sup.cR.sup.d-CR.sup.eR.sup.f-
(V.sup.2)-CR.sup.aR.sup.b-CR.sup.cR.sup.d-W*-CR.sup.eR.sup.f-
(V.sup.3)-CR.sup.aR.sup.b-CR.sup.cR.sup.dW*- (V.sup.4)
-CR.sup.aR.sup.b-W* - (V.sup.5) where each of the radicals R.sup.a,
R.sup.b, R.sup.c, R.sup.d, R.sup.e and R.sup.f in each case
independently of one another is hydrogen, halogen, nitro, cyano,
thiocyanato or a radical of the formula -B.sup.4-D.sup.4, W* is in
each case an oxygen atom, a sulfur atom or a group of the formula
N(B.sup.5-D.sup.5) and B.sup.3, B.sup.4, B.sup.5, D.sup.3, D.sup.4
and D.sup.5 are as defined hereinbelow, B.sup.1 and B.sup.5 in each
case independently of one another are a direct bond or a divalent
group of the formulae -C(=Z*)-, -C(=Z*)-Z**-, -C(=Z*)-NH- or
-C(=Z*)-NR*-, where Z*=an oxygen or sulfur atom, Z**=an oxygen or
sulfur atom and R*=(C.sub.1-C.sub.6)alkyl, aryl,
aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted,
B.sup.2, B.sup.3 and B.sup.4 in each case independently of one
another are a direct bond or a divalent group of the formulae -O-,
-S(O).sub.p-, -S(O).sub.p-O-, -O--S(O).sub.p-, -CO-, -O--CO-,
-CO--O-, -S--CO-, -CO--S-, -S--CS-, -CS--S-, -O--CO--O-,
-NR.sup.0-, -O-NR.sup.0-, -NR.sup.0-O-, -NR.sup.0-CO-,
-CO-NR.sup.0-, -O--CO-NR.sup.0- or -NR.sup.0-CO--O-, where p is the
integer 0, 1 or 2 and R.sup.O is hydrogen, (C.sub.1-C.sub.6)alkyl,
aryl, aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub- .6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted,
D.sup.1, D.sup.2, D.sup.3, D.sup.4 and D.sup.5 in each case
independently of one another are hydrogen, (C.sub.1-C.sub.6)alkyl,
aryl, aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted, or
in each case two radicals D.sup.3 of two groups -B.sup.3-D.sup.3
bound to one carbon atom are linked to each other and form an
alkylene group having 2 to 4 carbon atoms which is unsubstituted or
substituted by one or more radicals selected from the group
consisting of (C.sub.1-C.sub.4)alkyl and (C.sub.1-C.sub.4)alkoxy,
L.sup.0 is a direct bond, oxygen, sulfur or a group NG.sup.30 in
which the radical G.sup.30 is hydrogen, aryl which is unsubstituted
or substituted, or (C.sub.3-C.sub.9)cycloalkyl which is
unsubstituted or substituted, or heterocyclyl which is substituted
or unsubstituted, or (C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl or (C.sub.2-C.sub.6)alkynyl, where each of
the last-mentioned 3 radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, cyano, nitro, thiocyanato, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.2-C.sub.4)alkenyloxy,
(C.sub.2-C.sub.4)haloalkenyloxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl,
(C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, phenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, and radicals of the formulae R'-C(=Z')-,
R'-C(=Z')-Z-, R'-Z-C(=Z')-, -R'RN--C(=Z')-, R'-Z-C(=Z')-O-,
R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and R'RN--C(=Z')-NR'"-, where
R', R"and R'" in each case independently of one another are
hydrogen, (C.sub.1-C.sub.6)alkyl, aryl,
aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and
where Z and Z' independently of one another are in each case an
oxygen or sulfur atom, (X).sub.n is n substituents X, where the X
in each case independently of one another are halogen, hydroxyl,
amino, nitro, formyl, carboxyl, cyano, thiocyanato, aminocarbonyl
or (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylthio, mono(C.sub.1-C.sub.6)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkynyl, [(C.sub.1-C.sub.6)alkyl]carbonyl,
[(C.sub.1-C.sub.6)alkoxy]carbonyl,
mono(C.sub.1-C.sub.6)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocar- bonyl,
N-(C.sub.1-C.sub.6)alkanoylamino or
N-(C.sub.1-C.sub.4)alkanoyl-N-(- C.sub.1-C.sub.4)alkylamino, where
each of the last-mentioned 13 radicals is unsubstituted or
substituted, or (C.sub.3-C.sub.9)cycloalkyl,
(C.sub.3-C.sub.9)cycloalkoxy, (C.sub.3-C.sub.9)cycloalkylamino,
phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl,
heterocyclyloxy, heterocyclylthio or heterocyclylamino, where each
of the last-mentioned 11 radicals is unsubstituted or substituted,
or two adjacent radicals X together are a fused cycle having 4 to 6
ring atoms which is carbocyclic or contains hetero ring atoms
selected from the group consisting of O, S and N and which is
unsubstituted or substituted by one or more radicals selected from
the group consisting of halogen, (C.sub.1-C.sub.4)alkyl and oxo, n
is 0, 1, 2, 3, 4 or 5 and heterocyclyl in the abovementioned
radicals independently of one another in each case is a
heterocyclic radical having 3 to 7 ring atoms and 1 to 3 hetero
atoms selected from the group consisting of N, O and S.
2. A compound or a salt thereof as claimed in claim 1, wherein
R.sup.1 is phenyl, phenoxy, phenylthio, phenylamino,
N-phenyl-N-(C.sub.1-C.sub.4)alk- ylamino, where each of the
last-mentioned 5 radicals is unsubstituted or substituted by one or
more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 6 to 30 carbon atoms, or is (C.sub.3-C.sub.9)cycloalkyl which
is unsubstituted or substituted by one or more radicals selected
from the group consisting of halogen, hydroxyl, amino, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino and di(C.sub.1-C.sub.4)alkylamino
and, inclusive of substituents, has 3 to 30 carbon atoms, or is
heterocyclyl which is unsubstituted or substituted by one or more
radicals selected from the group consisting of halogen, hydroxyl,
amino, nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 2 to 30 carbon atoms, or is hydrogen or (C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.1-C.sub.6)alkoxy or (C.sub.1-C.sub.6)alkylthio, where each
of the last-mentioned 5 radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, cyano, nitro, thiocyanato, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.2-C.sub.4)alkenyloxy,
(C.sub.2-C.sub.4)haloalkenyloxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl,
(C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl and (C.sub.3-C.sub.6)cycloalkyl,
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, C.sub.1-C.sub.4)alkylthio,
C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino and
di(C.sub.1-C.sub.4)alkylamino, and phenyl and heterocyclyl, where
each of the two last-mentioned radicals is unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,
sulfonyl, cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.9)cycloalkyl,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl, and radicals of the formulae
R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-,
R'-Z-C(=Z')-O-, R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and
R'R"N--C(=Z')-NR'"-, where R', R" and R'" in each case
independently of one another are (C.sub.1-C.sub.4)alkyl, phenyl,
phenyl(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl or
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub- .4)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.3-C.sub.6)cycloalkyl and, in the case of cyclic radicals,
also (C.sub.1-C.sub.4)alkyl and (C.sub.1-C.sub.4)haloalkyl, and
where Z and Z' independently of one another are in each case one
oxygen or sulfur atom, and R.sup.2 is (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of the radicals A), B), C) and
D), where group A) consists of the radicals halogen, hydroxyl,
amino, nitro, formyl, carboxyl, aminocarbonyl, sulfo, cyano,
thiocyanato and oxo, group B) consists of the radicals
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylth- io, mono(C.sub.1-C.sub.6)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkynyl, (C.sub.3-C.sub.9)cycloalkyl,
(C.sub.4-C.sub.9)cycloalkenyl, (C.sub.1-C.sub.6)alkylidene,
(C.sub.4-C.sub.9)cycloalkylidene, radicals of the formulae
R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-,
R'-Z-C(=Z')-O-, R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and
R'R"N--C(=Z')-NR'"-, where R', R"and R'" in each case independently
of one another are hydrogen, (C.sub.1-C.sub.6)alkyl, phenyl,
phenyl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl and where Z and
Z' independently of one another are in each case an oxygen or
sulfur atom, group C) consists of radicals as defined for group B),
but where each radical is substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
nitro, formyl, carboxyl, sulfo, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, (C.sub.4-C.sub.9)cycloalkylene
(C.sub.4-C.sub.9)cycloalkylidene, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl, phenyl, phenoxy, phenylthio,
phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and
heterocyclylamino, where each of the last-mentioned 21 radicals is
unsubstituted or substituted by one or more radicals selected from
the group consisting of halogen, nitro, cyano,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkoxy, formyl, (C.sub.1-C.sub.4)alkylcarbonyl
and (C.sub.1-C.sub.4)alkoxycarbonyl and, in the case of cyclic
radicals, also (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl
and (C.sub.1-C.sub.6)alkylidene, and, in the case of cyclic
radicals, also (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl
and (C.sub.1-C.sub.6)alkylidene, and group D) consists of divalent
or trivalent aliphatic bridges having 1 to 6, preferably 1 to 4,
carbon atoms which, in the case of divalent bridges, connect two
and, in the case of trivalent bridges, three carbon atoms of the
cyclic skeleton and the radical R.sup.2 thus constitutes the
radical of a bicyclic or tricyclic system, where each of the
bridges is unsubstituted or substituted by one or more substituents
selected from the group consisting of halogen, nitro, cyano,
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)haloalkoxy, formyl,
(C.sub.1-C.sub.4)alkylcarbonyl, (C.sub.1-C.sub.4)alkoxycarbonyl and
oxo, and where R.sup.2, inclusive of substituents, has 3 to 20
carbon atoms, or R.sup.2 is (C.sub.4-C.sub.9)cycloalkenyl which is
unsubstituted or substituted by one or more radicals selected from
the group consisting of the radicals A), B), C) and D) as are
defined as radicals for the case where
R.sup.2=(C.sub.3-C.sub.9)cycloalkyl and, in this context, inclusive
of substituents has 4 to 20 carbon atoms, or R.sup.2 is
heterocyclyl which is unsubstituted or substituted by one or more
radicals selected from the group consisting of the radicals A), B),
C) and D) as are defined as radicals for the case where
R.sup.2=(C.sub.3-C.sub.9)cycloalky- l, or R.sup.2 is phenyl which
is unsubstituted or substituted by one or more radicals selected
from the group consisting of the radicals A), B) and C) as are
defined as radicals for R.sup.2=(C.sub.3-C.sub.9)cycloalkyl- ,
where R.sup.2 inclusive of substituents has up to 20 carbon
atoms.
3. A compound or a salt thereof as claimed in claim 1, wherein
R.sup.3 is a radical of the formula 40where R.sup.6 and R.sup.7
together with the nitrogen atom of the group NR.sup.6R.sup.7,
R.sup.7 and OR.sup.8 together with the nitrogen atom of the group
NOR.sup.8R.sup.7, R.sup.7 and SR.sup.8 together with the nitrogen
atom of the group NSR.sup.8R.sup.7, R.sup.10 and R.sup.11 together
with the nitrogen atom of the group NR.sup.10R.sup.11, OR.sup.12
and OR.sup.13, or SR.sup.12 and SR.sup.13, together with the carbon
atom of the 41respectively, OR.sup.9 and R.sup.14 or SR.sup.9 and
R.sup.14 together with the carbon atom of the groups
42respectively, R.sup.14 and R.sup.15 together with the carbon atom
of the group 43R.sup.5 and R.sup.7 together with the atom group 44
45R.sup.5 and R.sup.17 together with the carbon atom of the group
46R.sup.5 and R.sup.16 together with the atom group 47R.sup.7 and
R.sup.10 together with the atom group 48in each case independently
of one another form a carbocyclic or heterocyclic ring having 3 to
7 ring atoms and 1 to 6 hetero atoms, the optional further hetero
ring atoms being selected from the group consisting of N, O and S
and the carbocyclic or heterocyclic ring in each case being
unsubstituted or substituted, and the radicals R.sup.5, R.sup.6,
R.sup.7, R.sup.8, R.sup.9, R.sup.10, R .sup.11, R.sup.14, R.sup.15,
R.sup.16, R.sup.17 in the above formulae independently of one
another are hydrogen, aryl which is unsubstituted or substituted,
or (C.sub.3-C.sub.9)Cycloalkyl which is unsubstituted or
substituted, or heterocyclyl which is unsubstituted or substituted,
or (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl or
(C.sub.2-C.sub.6)alkynyl, where each of the last-mentioned 3
radicals is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, cyano,
nitro, thiocyanato, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.2-C.sub.4)alkenyloxy,
(C.sub.2-C.sub.4)haloalkenyloxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl,
(C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, phenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, and radicals of the formulae R'--C(=Z')-,
R'--C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-, R'-Z-C(=Z')-O-,
R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and R'R"N--C(=Z')-NR'"-, where
R', R" and R'" in each case independently of one another are
hydrogen, (C.sub.1-C.sub.6)alkyl, aryl,
aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and
where Z and Z' independently of one another are in each case an
oxygen or sulfur atom, and R.sup.12, R.sup.13 in each case
independently of one another are aryl which is unsubstituted or
substituted, or (C.sub.3-C.sub.9)cycloalkyl which is unsubstituted
or substituted, or heterocyclyl which is substituted or
unsubstituted, or (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl
or (C.sub.2-C.sub.6)alkynyl, where each of the last-mentioned 3
radicals is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, cyano,
nitro, thiocyanato, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.2-C.sub.4)alkenyloxy,
(C.sub.2-C.sub.4)haloalkenyloxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl,
(C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, phenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, and radicals of the formulae R'--C(=Z')-,
R'--C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-, R'-Z-C(=Z')-O-,
R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and R'R"N--C(=Z')-NR'"-, where
R', R" and R'" in each case independently of one another are
(C.sub.1-C.sub.6)alkyl, aryl, aryl-(C.sub.1-C.sub.6)alkyl- ,
(C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.su- b.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and
where Z and Z' independently of one another are in each case one
oxygen or sulfur atom,
4. A compound or a salt thereof as claimed in claim 1, wherein
R.sup.4 is hydrogen, (C.sub.1-C.sub.4)alkyl, phenyl or
(C.sub.3-C.sub.6)cycloalkyl, where each of the 3 last-mentioned
radicals is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
((C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfonyl
and, in the case of cyclic radicals, also (C.sub.1-C.sub.4)alkyl
and (C.sub.1-C.sub.4)haloalkyl, or is formyl,
[(C.sub.1-C.sub.4)alkyl]carbony- l,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl or
di(C.sub.1-C.sub.4)alkylaminoc- arbonyl; and L.sup.0 is a direct
bond or oxygen, A.sup.1 is straight-chain alkylene having 1 to 5
carbon atoms or straight-chain alkenylene or alkynylene having in
each case 2 to 5 carbon atoms, where each of the three
last-mentioned diradicals is unsubstituted or substituted by one or
more radicals selected from the group consisting of halogen, nitro,
cyano, thiocyanato and a radical of the formula -B.sup.2-D.sup.2,
in which B.sup.2 is a direct bond or a divalent group of the
formulae -O-, -SO.sub.2-, -CO-, -O--CO-, -NR.sup.0-, -NR.sup.0-CO-,
-CO-NR.sup.0-, -O--CO-NR.sup.0- or -NR.sup.0-CO--O-, in which
R.sup.O independently of one another are in each case hydrogen,
(C.sub.1-C.sub.4)alkyl, phenyl, phenyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.6)cycloalkyl or
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.4)alkyl, where each of
the last-mentioned 5 radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfonyl
and, in the case of cyclic radicals, also (C.sub.1-C.sub.4)alkyl
and (C.sub.1-C.sub.4)haloalkyl, A.sup.2 is a direct bond or a group
of the formula -CH.sub.2-, -CH.sub.2CH.sub.2-,
-CH.sub.2CH.sub.2CH.sub.2- or -CH.sub.2CH.sub.2CH.sub.2CH.sub.2,
where each of the 4 last-mentioned diradicals is unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, nitro, cyano, thiocyanato and radicals of
the formula -B.sup.3-D.sup.3, or a divalent radical of the formula
V.sup.1, V.sup.2, V.sup.3, V.sup.4 or V.sup.5,
-CR.sup.aR.sup.b-W*-CR.sup.cR.sup.d-(V.sup.1)
-CR.sup.aR.sup.b-W*-CR.sup.- cR.sup.d-CR.sup.eR.sup.f-(V2)
-CR.sup.aR.sup.b-CR.sup.cR.sup.d-W*-CR.sup.e- R.sup.f-(V3)
-CR.sup.aR.sup.b-CR.sup.cR.sup.d-W*-(V.sup.4) -CR.sup.aR.sup.b-W*-
(V.sup.5), where each of the radicals R.sup.a to R.sup.f in each
case independently of one other is hydrogen, halogen, nitro, cyano,
thiocyanato or a radical of the formula -B.sup.4-D.sup.4, W* is in
each case O, S or a group of the formula N(B.sup.5-D.sup.5), and
B.sup.5 is a direct bond or a divalent group of the formulae
-C(=Z*)-, -C(=Z*)-Z**-, -C(=Z*)-NH- or -C(=Z*)-NR*-, where Z*=O or
S, Z**=O or S and R*=(C.sub.1-C.sub.4)alkyl, phenyl,
phenyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl or
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub- .4)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted,
B.sup.2, B.sup.3 and B.sup.4 in each case independently of one
another are a direct bond or a divalent group of the formulae -O-,
-S(O).sub.p-, -S(O).sub.p-O-, -O--S(O).sub.p-, -CO-, -O--CO-,
-CO--O-, -S--CO-, -CO--S-, -S--CS-, -CS--S-, -O--CO--O-,
-NR.sup.0-, -O-NR.sup.0-, -NR.sup.0-O-, -NR.sup.0-CO-,
-CO-NR.sup.0-, -O--CO-NR.sup.0- or -NR.sup.0-CO--O-, where p is the
integer 0, 1 or 2 and R.sup.0=hydrogen, (C.sub.1-C.sub.4)alkyl,
phenyl, phenyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl
or (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub- .4)alkyl, where each
of the 5 last-mentioned radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfonyl
and, in the case of cyclic radicals, also (C.sub.1-C.sub.4)alkyl
and (C.sub.1-C.sub.4)haloalkyl, and D.sup.2, D.sup.3, D.sup.4 and
D.sup.5 independently of one another are hydrogen,
(C.sub.1-C.sub.6)alkyl, phenyl, phenyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.6)cycloalkyl or
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted.
5. A compound or a salt thereof as claimed in claim 1, wherein
(X).sub.n is n substituents X, where X preferably in each case
independently of one another are halogen, hydroxyl, amino, nitro,
formyl, carboxyl, cyano, thiocyanato, aminocarbonyl or
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)alkynyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocar- bonyl,
N-(C.sub.1-C.sub.6)alkanoylamino or
N-(C.sub.1-C.sub.4)alkanoyl-N-(- C.sub.1-C.sub.4)alkylamino, where
each of the last-mentioned 13 radicals is unsubstituted or
substituted, preferably unsubstituted or substituted by one or more
radicals selected from the group consisting of halogen, hydroxyl,
amino, cyano, thiocyanato, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkylamino,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl, phenyl, phenoxy, phenylthio,
phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and
heterocyclylamino, where each of the last-mentioned 8 radicals is
unsubstituted or has one or more substituents selected from the
group consisting of halogen, nitro, cyano, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy, formyl,
(C.sub.1-C.sub.4)alkylcarbonyl and (C.sub.1-C.sub.4)alkoxycarbonyl,
or is (C.sub.3-C.sub.9)cycloalkyl, phenyl, phenoxy, phenylthio,
phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio or
heterocyclylamino, where each of the last-mentioned 9 radicals is
unsubstituted or substituted, preferably unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,
cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio, (C.sub.1
-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.6)cycloalkyl,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl and
di(C.sub.1-C.sub.4)alkylaminocarbonyl, or two adjacent radicals X
together are a fused cycle having 4 to 6 ring atoms which is
carbocyclic or contains hetero ring atoms selected from the group
consisting of O, S and N and which is unsubstituted or substituted
by one or more radicals selected from the group consisting of
halogen, (C.sub.1-C.sub.4)alkyl and oxo, and n is 0, 1, 2 or 3.
6. A process for the preparation of a compound of the formula (I)
or a salt thereof as defined in claim 1, 49where A.sup.1, A.sup.2,
L.sup.0, R.sup.1, R.sup.2, R.sup.3, R.sup.4, X and n are as defined
in formula (I) in claim 1, wherein a) in the event that R.sup.3 in
formula (I) is a group of the formula -L.sup.1-N.dbd.C(U)(U.sup.3),
where L.sup.1, U.sup.1 and U.sup.3 are as defined under R.sup.3 in
formula (I), a compound of the formula (II) 50where A.sup.1,
A.sup.2, L.sup.0, L.sup.1, R.sup.1, R.sup.2, R.sup.4, X and n are
as defined in formula (I), is reacted with a compound of the
formula (Ill) 51where U.sup.1 and U.sup.3 are as defined in formula
(I) and R.sup.15 and R.sup.19 independently of one another are
unsubstituted or substituted alkyl having up to 12 carbon atoms, or
jointly linked are an alkylene group having 2 to 4 carbon atoms, or
b) in the event that R.sup.3 in formula (I) is a group of the
formula L.sup.1-NG.sup.1-C(U.sup.2)=N--U.sup.4 where L.sup.1,
G.sup.1, U.sup.2 and U.sup.4 are as defined under R.sup.3 in
formula (I), a compound of the formula (IV) 52where A.sup.1,
A.sup.2, L.sup.0, L.sup.1, R.sup.1, R.sup.2, R.sup.4, G.sup.1, X
and n are as defined in formula (I) in claim 1 is reacted with a
compound of the formula (V) 53where U.sup.2 and U.sup.4 are as
defined in formula (I) and R.sup.18 is as defined in formula (III)
in variant a) of the present claim, or c) in the event that R.sup.3
in formula (I) is a group of the formula -L.sup.1-N.dbd.C(U.sup.1-
)(U.sup.3) where U.sup.3.dbd.NG.sup.18NG.sup.19G.sup.20,
NG.sup.21OG.sup.22 or NG.sup.23SG.sup.24 and L.sup.1, U.sup.1,
G.sup.18, G.sup.19, G.sup.20, G.sup.21, G.sup.22, G.sup.23,
G.sup.24 are as defined under R.sup.3 in formula (I), a compound of
the formula (VI) 54where A.sup.1, A.sup.2, L.sup.0, L.sup.1,
R.sup.1, R.sup.2, R.sup.4, U.sup.1, X and n are as defined in
formula (I) and R.sup.6 and R.sup.7 are as defined under R.sup.3 in
formula (I) are reacted with a compound of the formula (VII) or its
acid adducts H--U.sup.3 (VII) where U.sup.3 is as defined in
formula (I), or d) in the event that R.sup.3 in formula (I) is a
group of the formula -L.sup.1-N.dbd.C(U.sup.1)(U.sup.3) where
U.sup.1=R.sup.14 and U.sup.3=R.sup.15 and where L.sup.1, R.sup.14
and R.sup.15 are as defined under R.sup.3 in claim 3, a compound of
the formula (II) as defined in variant a) of the present claim is
reacted with an aldehyde or ketone of the formula
(VIII)U.sup.1--CO--U.sup.3 (VIII)where U.sup.1 and U.sup.3 are as
defined in formula (I).
7. A herbicidal or plant-growth-regulating composition, which
comprises one or more compounds of the formula (I) or their salts
as claimed in claims 1 and formulation auxiliaries applicable in
crop protection.
8. A method of controlling harmful plants or for regulating the
growth of plants, which comprises applying an active amount of one
or more compounds of the formula (I) or their salts as claimed in
claim 1 to the plants, plant seeds or the area under
cultivation.
9. The use of compounds of the formula (I) or their salts as
claimed in claim 1 as herbicides or plant growth regulators.
10. The use as claimed in claim 9, wherein the compounds of the
formula (I) or their salts are employed for controlling harmful
plants or for regulating the growth of crops of useful plants or
ornamentals.
Description
[0001] The invention relates to the technical field of the crop
protection agents, such as herbicides and plant growth regulators,
in particular of the herbicides for selectively controlling harmful
plants in crops of useful plants.
[0002] It is known that
2-amino-4-(N-phenylalkylamino)-1,3,5-triazines which are
substituted in the 6-position and which can be further substituted
have herbicidal and plant-growth-regulatory properties; cf. WO
97/08156 and literature cited therein, WO 99/37627 and literature
cited therein, WO 98/15537 and literature cited therein; cf. to
some extent also WO 97/00254 and literature cited therein.
[0003] In some cases, the known active substances have
disadvantages when used, be it an insufficient herbicidal action
against harmful plants, too narrow a weed plant spectrum which can
be controlled with an active substance, or too little selectivity
in crops of useful plants. Other active substances cannot be
prepared economically on an industrial scale, owing to precursors
and reagents which are not easily available; in the case of others,
the chemical stability is insufficient.
[0004] The object of the present invention is to provide
alternative active substances of the 2-amino-1,3,5-triazine type
which can be employed as herbicides or plant-growth regulators, if
appropriate advantageously.
[0005] Subject matter of the present invention are compounds of the
formula (I) and their salts 2
[0006] in which
[0007] R.sup.1 is aryl, aryloxy, arylthio, arylamino,
N-aryl-N-(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.9)cycloalkyl,
(C.sub.3-C.sub.9)cycloalkyloxy, (C.sub.3-C.sub.9)cycloalkylthio,
(C.sub.3-C.sub.9)cycloalkylamino,
N-(C.sub.3-C.sub.9)cycloalkyl-N-(C.sub.- 1-C.sub.4)alkylamino,
di-[(C.sub.3-C.sub.9)cycloalkyl]amino, heterocyclyl,
heterocyclyloxy, heterocyclylthio, heterocyclylamino or
N-heterocyclyl-N-(C.sub.1-C.sub.4)alkylamino, where each of the
last-mentioned 16 radicals is unsubstituted or substituted,
preferably unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
nitro, formyl, carboxyl, sulfo, cyano, thiocyanato,
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl,
(C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy,
(C.sub.2-C.sub.6)alkenyloxy, (C.sub.2-C.sub.6)haloalkenyloxy,
(C.sub.2-C.sub.6)alkynyloxy, (C.sub.2-C.sub.6)haloalkynyoxy,
(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio,
mono(C.sub.1-C.sub.6)alkylamino, di(C.sub.1-C.sub.6)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, (C.sub.5-C.sub.9)cycloalkenyl,
[(C.sub.1-C.sub.5)alkyl]carbonyl,
[(C.sub.1-C.sub.6)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.6)al- kylaminocarbonyl,
di(C.sub.1-C.sub.6)alkylaminocarbonyl,
(C.sub.1-C.sub.6)alkylsulfonyl and
(C.sub.1-C.sub.6)haloalkylsulfonyl, and, inclusive of substituents,
preferably has up to 30 carbon atoms, or
[0008] is hydrogen, (C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.2-C.sub.6)alkenyloxy,
(C.sub.2-C.sub.6)alkynyloxy, (C.sub.1-C.sub.6)alkylthio,
(C.sub.2-C.sub.6)alkenylthio, (C.sub.2-C.sub.6)alkynylthio,
(C.sub.1-C.sub.6)alkylamino or
di-[(C.sub.1-C.sub.6)alkyl]amino,
[0009] where each of the last-mentioned 11 radicals can be
unsubstituted or substituted by one or more radicals selected from
the group consisting of halogen, hydroxyl, cyano, nitro,
thiocyanato, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.2-C.sub.4)alkenyloxy, (C.sub.2-C.sub.4)haloalkenyloxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulfinyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, phenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, and radicals of the formulae R'-C(=Z')-,
R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-, R'-Z-C(=Z')-O-,
R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and R'R"N--C(=Z')-NR'"-,
[0010] where R', R" and R'" in each case independently of one
another are hydrogen or, preferably, (C.sub.1-C.sub.6)alkyl, aryl,
aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3C.sub.9)cycloalkyl or
(C.sub.3C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted, and
where Z and Z' independently of one another are in each case an
oxygen or sulfur atom,
[0011] and, inclusive of substituents, preferably has 1 to 30
carbon atoms,
[0012] R.sup.2 is (C.sub.3C.sub.9)cycloalkyl which is unsubstituted
or substituted, (C.sub.4-C.sub.9)cycloalkenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, or phenyl which is unsubstituted or substituted,
where R.sup.2, inclusive of substituents, preferably has up to 30
carbon atoms, R.sup.3 is a group 3
[0013] in which
[0014] L.sup.1 is a direct bond, -O-, -S- or a group of the formula
-NG.sup.2-, preferably a direct bond,
[0015] U.sup.1, U.sup.2 independently of one another are a group of
the formula G.sup.3, OG.sup.4, SG.sup.5, NG.sup.6G.sup.7,
NG.sup.8NG.sup.9G.sup.10, NG.sup.11OG.sup.12 or
NG.sup.11SG.sup.12,
[0016] U.sup.3 is a group of the formula G.sup.13, OG.sup.14,
SG.sup.15, NG.sup.16G.sup.17, NG.sup.18NG.sup.19G.sup.20,
NG.sup.21OG.sup.22 or NG.sup.23SG.sup.24,
[0017] U.sup.4 is a group of the formula G.sup.25, OG.sup.26,
SG.sup.27 or NG.sup.28G.sup.29,
[0018] where the radicals G.sup.1 to G.sup.29 independently of one
another are hydrogen, aryl which is unsubstituted or substituted
and, inclusive of substituents, preferably has 6 to 30 carbon
atoms, or (C.sub.3-C.sub.9)cycloalkyl which is unsubstituted or
substituted and, inclusive of substituents, preferably has 3 to 30
carbon atoms, or heterocyclyl which is substituted or unsubstituted
and, inclusive of substituents, preferably has 2 to 30 carbon
atoms, or are (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl or
(C.sub.2-C.sub.6)alkynyl,
[0019] where each of the last-mentioned 3 radicals is unsubstituted
or substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, cyano, nitro, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.2-C.sub.4)alkenyloxy, (C.sub.2-C.sub.4)haloalkenyloxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulfinyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, phenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, and radicals of the formulae R'-C(=Z')-,
R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R-N--C(=Z')-, R'-Z-C(=Z)-O-,
R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and R'R"N--C(=Z')-NR'"-,
where
[0020] R', R" and R'" in each case independently of one another are
hydrogen or, preferably, (C.sub.1-C.sub.6)alkyl, aryl,
aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and
where Z and Z' independently of one another are in each case an
oxygen or sulfur atom, and, inclusive of substituents, preferably
has 1 to 30 carbon atoms,
[0021] or the radicals U.sup.1 and U.sup.3 or U.sup.2 and U.sup.4
or U.sup.2 and G.sup.1 or U.sup.4 and G.sup.1, as a pair, together
with the atoms linking them are in each case a carbocyclic or
heterocyclic ring having 4 to 7 ring atoms, the ring being
unsubstituted or substituted,
[0022] R.sup.4 is a radical of the formula -B.sup.1-D.sup.1, where
B.sup.1 and D.sup.1 are as defined hereinbelow, and R.sup.4,
inclusive of substituents, preferably has up to 20 carbon
atoms,
[0023] A.sup.1 is a direct bond or straight-chain alkylene having 1
to 5 carbon atoms or straight-chain alkenylene or alkynylene having
in each case 2 to 5 carbon atoms, where each of the three
last-mentioned diradicals is unsubstituted or substituted by one or
more radicals selected from the group consisting of halogen, nitro,
cyano, thiocyanato and radicals of the formula --B.sup.2-D.sup.2,
where B.sup.2 and D.sup.2 are as defined hereinbelow,
[0024] A.sup.2 is a direct bond or straight-chain alkylene having 1
to 4 carbon atoms or straight-chain alkenylene or alkynylene having
in each case 2 to 5 carbon atoms, where each of the three
last-mentioned diradicals is unsubstituted or substituted by one or
more radicals selected from the group consisting of halogen, nitro,
cyano, thiocyanato and radicals of the formula --B.sup.3-D.sup.3,
or a divalent radical of the formula V.sup.1, V.sup.2, V.sup.3,
V.sup.4 or V.sup.5,
[0025] -CR.sup.aR.sup.b-W*-CR.sup.cR.sup.d-(V.sup.1)
[0026] -CR.sup.aR.sup.b-W*-CR.sup.cR.sup.d-CR.sup.eR.sup.f-(V2)
[0027] -CR.sup.aR.sup.b-CR.sup.cR.sup.d-W*-CR.sup.eR.sup.f-(V3)
[0028] -CR.sup.aR.sup.b-CR.sup.cR.sup.d-W*-(V.sup.4)
[0029] -CR.sup.aR.sup.b-W*- (V.sup.5),
[0030] where each of the radicals R.sup.a, R.sup.b, R.sup.c,
R.sup.d, R.sup.e and R.sup.f in each case independently of one
another is hydrogen, halogen, nitro, cyano, thiocyanato or a
radical of the formula --B.sup.4-D.sup.4,
[0031] W* is in each case an oxygen atom, a sulfur atom or a group
of the formula N(B.sup.5-D.sup.5) and
[0032] B.sup.3, B.sup.4, B.sup.5, D.sup.3, D.sup.4 and D.sup.5 are
as defined hereinbelow,
[0033] B.sup.1 and B.sup.5 in each case independently of one
another are a direct bond or a divalent group of the formulae
-C(=Z*)-, -C(=Z*)-Z**-, -C(=Z*)NH- or -C(=Z*)-NR*-, where Z* =an
oxygen or sulfur atom, Z**=an oxygen or sulfur atom and
R*=(C.sub.1-C.sub.6)alkyl, aryl, aryl-(C.sub.1-C.sub.6)alkyl,
(C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and,
inclusive of substituents, preferably has up to 20 carbon
atoms,
[0034] B.sup.2, B.sup.3 and B.sup.4 in each case independently of
one another are a direct bond or a divalent group of the formulae
-O-, -S(O).sub.p-, -S(O).sub.p-O-, -O--S(O).sub.p-, -CO-, -O--CO-,
-CO--O-, -S--CO-, -CO--S-, -S--CS-, -CS--S-, -O--CO--O-,
-NR.sup.0-, -O-NR.sup.0-, -NR.sup.0-O-, -NR.sup.0-CO-,
-CO-NR.sup.0-, -O--CO-NR.sup.0- or -NR.sup.0-CO--O-, where p is the
integer 0, 1 or 2 and R.sup.O is hydrogen, (C.sub.1-C.sub.6)alkyl,
aryl, aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub- .6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and,
inclusive of substituents, preferably has up to 20 carbon
atoms,
[0035] D.sup.1, D.sup.2, D.sup.3, D.sup.4 and D.sup.5 in each case
independently of one another are hydrogen, (C.sub.1-C.sub.6)alkyl,
aryl, aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and,
inclusive of substituents, preferably has up to 20 carbon
atoms,
[0036] or in each case two radicals D.sup.3 of two groups
--B.sup.3-D.sup.3 bound to one carbon atom are linked to each other
and form an alkylene group having 2 to 4 carbon atoms which is
unsubstituted or substituted by one or more radicals selected from
the group consisting of (C.sub.1-C.sub.4)alkyl and
(C.sub.1-C.sub.4)alkoxy,
[0037] L.sup.0 is a direct bond, oxygen, sulfur or a group
NG.sup.30 in which the radical G.sup.30 is hydrogen, aryl which is
unsubstituted or substituted and, inclusive of substituents,
preferably has 6 to 30 carbon atoms, or (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted and, inclusive of
substituents, preferably has 3 to 30 carbon atoms, or heterocyclyl
which is substituted or unsubstituted and, inclusive of
substituents, preferably has 2 to 30 carbon atoms, or is
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl or
(C.sub.2-C.sub.6)alkynyl,
[0038] where each of the last-mentioned 3 radicals is unsubstituted
or substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, cyano, nitro, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.2-C.sub.4)alkenyloxy, (C.sub.2-C.sub.4)haloalkenyloxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulfinyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, phenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, and radicals of the formulae R'-C(=Z')-,
R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-, R'-Z-C(=Z')-O-,
R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and R'R"N--C(=Z')-NR'"-,
where
[0039] R', R" and R'" in each case independently of one another are
hydrogen or, preferably, (C.sub.1-C.sub.6)alkyl, aryl,
aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and
where Z and Z' independently of one another are in each case an
oxygen or sulfur atom,
[0040] and, inclusive of substituents, preferably has 1 to 30
carbon atoms,
[0041] (X).sub.n is n substituents X, where the X in each case
independently of one another are halogen, hydroxyl, amino, nitro,
formyl, carboxyl, cyano, thiocyanato, aminocarbonyl or
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkylthio, mono(C.sub.1-C.sub.6)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkynyl, [(C.sub.1-C.sub.6)alkyl]carbonyl,
[(C.sub.1-C.sub.6)alkoxy]carbonyl,
mono(C.sub.1-C.sub.6)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocar- bonyl,
N-(C.sub.1-C.sub.6)alkanoylamino or
N-(C.sub.1-C.sub.4)alkanoyl-N-(- C.sub.1-C.sub.4)alkylamino,
[0042] where each of the last-mentioned 13 radicals is
unsubstituted or substituted, preferably unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,
cyano, thiocyanato, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.9)cycloalkyl,
(C.sub.3-C.sub.9)cycloalkylamino, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl, phenyl, phenoxy, phenylthio,
phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and
heterocyclylamino,
[0043] where each of the last-mentioned 8 radicals is unsubstituted
or has one or more substituents selected from the group consisting
of halogen, nitro, cyano, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy, formyl,
(C.sub.1-C.sub.4)alkylcarbonyl and
(C.sub.1-C.sub.4)alkoxycarbonyl,
[0044] or is (C.sub.3-C.sub.9)cycloalkyl,
(C.sub.3-C.sub.9)cycloalkoxy, (C.sub.3-C.sub.9)cycloalkylamino,
phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl,
heterocyclyloxy, heterocyclylthio or heterocyclylamino,
[0045] where each of the last-mentioned 11 radicals is
unsubstituted or substituted, preferably unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,
cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.9)cycloalkyl,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl and
Di(C.sub.1-C.sub.4)alkylaminocarbonyl,
[0046] or two adjacent radicals X together are a fused cycle having
4 to 6 ring atoms which is carbocyclic or contains hetero ring
atoms selected from the group consisting of O, S and N and which is
unsubstituted or substituted by one or more radicals selected from
the group consisting of halogen, (C.sub.1-C.sub.4)alkyl and
oxo,
[0047] n is 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in
particular 0, 1 or 2, and heterocyclyl in the abovementioned
radicals independently of one another in each case is a
heterocyclic radical having 3 to 7 ring atoms and 1 to 3 hetero
atoms selected from the group consisting of N, O and S.
[0048] Unless specified in greater detail, divalent radicals, for
example B.sup.1=-C(=Z*)-Z** -, are defined such that, in the
composite groups, for example - B.sup.1-D.sup.1, it is the bond of
the divalent radical that is written on the right in the formula
for the divalent radical which is linked to the group D.sup.1, i.e.
- B.sup.1-D.sup.1 is a group of the formula -C(=Z*)-Z**-D.sup.1;
this applies similarly to analogous divalent radicals.
[0049] The compounds of the formula (I) can form salts by addition
of a suitable inorganic or organic acid such as, for example, HCl,
HBr, H.sub.2SO.sub.4 or HNO.sub.3, but also oxalic acid or sulfonic
acids, to a basic group such as, for example, amino or alkylamino.
Suitable substituents which are present in deprotonated form such
as, for example, sulfonic acids or carboxylic acids, can form
internal salts with groups which are protonable themselves, such as
amino groups. Likewise, salts can be formed by replacing the
hydrogen in suitable substituents such as, for example, sulfonic
acids or carboxylic acids, by an agriculturally suitable cation.
These salts are, for example, metal salts, in particular alkali
metal salts or alkaline earth metal salts, in particular sodium
salts and potassium salts, or else ammonium salts, salts with
organic amines, or quaternary ammonium salts.
[0050] In formula (I) and all subsequent formulae, the radicals
alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and
the corresponding unsaturated and/or substituted radicals can be in
each case straight-chain or branched in the carbon skeleton. Unless
specifically indicated, the lower carbon skeletons, for example
those having 1 to 6 carbon atoms or, in the case of unsaturated
groups, 2 to 6 carbon atoms, are preferred for these radicals.
Alkyl radicals, also in the composite meanings such as alkoxy,
haloalkyl and the like, are, for example, methyl, ethyl, n- or
i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl,
i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl,
1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals
have the meanings of the possible unsaturated radicals which
correspond to the alkyl radicals; alkenyl is, for example, allyl,
1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,
but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl;
alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl,
1-methylbut-3-yn-1-yl.
[0051] Cycloalkyl is a carbocyclic, saturated ring system having
preferably 3-8 carbon atoms, for example cyclopropyl, cyclobutyl,
cyclopentyl or cyclohexyl. In the case of substituted cycloalkyl,
this encompasses cyclic systems with substituents, where the
substituents are bonded to the cycloalkyl radical by a double bond,
for example, an alkylidene group such as methylidene. In the case
of substituted cycloalkyl, this also encompasses polycyclic
aliphatic systems such as, for example, bicyclo[1.1.0]butan-1-yl,
bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl,
bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl,
adamantan-1-yl and adamantan-2-yl.
[0052] Cycloalkenyl is a carbocyclic, nonaromatic, partially
unsaturated ring system having preferably 4-8 carbon atoms, for
example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl,
2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl,
2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or
1,4-cyclohexadienyl. In the case of substituted cycloalkenyl, what
has been said for substituted cycloalkyl applies analogously.
[0053] Halogen is, for example, fluorine, chlorine, bromine or
iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl or
alkynyl, respectively, each of which is partially or fully
substituted by, preferably, fluorine, chlorine and/or bromine, in
particular by fluorine or chlorine, for example monohaloalkyl,
perhaloalkyl, CF.sub.3, CHF.sub.2, CH.sub.2F, CF.sub.3CF.sub.2,
CH.sub.2FCHCl, CCl.sub.3, CHCl.sub.2, CH.sub.2CH.sub.2Cl;
haloalkoxy is, for example, OCF.sub.3, OCHF.sub.2, OCH.sub.2F,
CF.sub.3CF.sub.2O, OCH.sub.2CF.sub.3 and OCH.sub.2CH.sub.2Cl; this
also applies analogously to haloalkenyl and other
halogen-substituted radicals.
[0054] Aryl is a mono-, bi- or polycyclic aromatic system, for
example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl,
pentalenyl, fluorenyl and the like, preferably phenyl.
[0055] A heterocyclic radical or ring (heterocyclyl) can be
saturated, unsaturated or heteroaromatic; it preferably contains
one or more, in particular 1, 2 or 3, hetero atoms in the
heterocyclic ring, preferably selected from the group consisting of
N, O and S; it is preferably an aliphatic heterocyclyl radical
having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6
ring atoms. The heterocyclic radical can be, for example, a
heteroaromatic radical or ring (heteroaryl) such as, for example, a
mono-, bi- or polycyclic aromatic system in which at least 1 ring
contains one or more hetero atoms, for example pyridyl,
pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl,
thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl,
imidazolyl and triazolyl, or it is a partially or fully
hydrogenated radical such as oxiranyl, oxetanyl, oxolanyl
(=tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl, piperazinyl,
dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl
and morpholinyl. Suitable substituents for a substituted
heterocyclic radical are the substituents stated further below, and
additionally also oxo. The oxo group can also be present at those
hetero ring atoms where various oxidation numbers are possible, for
example in the case of N and S.
[0056] Substituted radicals such as a substituted alkyl, alkenyl,
alkynyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical
are, for example, a substituted radical which is derived from the
unsubstituted skeleton, the substituents being, for example, one or
more, preferably 1, 2 or 3, radicals selected from the group
consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl,
amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl,
alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl,
substituted amino such as acylamino, mono- and dialkylamino, and
alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl
and, in the case of cyclic radicals, also alkyl and haloalkyl.
[0057] In this context, "one or more radicals selected from the
group consisting of" in the definition are to be understood as
meaning in each case one or more identical or different radicals
selected from the stated group of radicals, unless specific
limitations are defined expressly.
[0058] The term "substituted radicals" such as substituted alkyl
and the like includes, in addition to the saturated
hydrocarbon-containing radicals stated, corresponding unsaturated
aliphatic and aromatic radicals such as unsubstituted or
substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl,
phenoxy and the like, as substituents. In the case of substituted
cyclic radicals with aliphatic moieties in the ring, this also
encompasses cyclic systems with those substituents which are bonded
to the ring by a double bond, for example which are substituted by
an alkylidene group such as methylidene or ethylidene.
[0059] In the case of radicals with carbon atoms, those having 1 to
4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred.
Substituents which are preferred are, as a rule, those selected
from the group consisting of halogen, e.g. fluorine and chlorine,
(C.sub.1-C.sub.4)alkyl, preferably methyl or ethyl,
(C.sub.1-C.sub.4)haloalkyl, preferably trifluoromethyl,
(C.sub.1-C.sub.4)alkoxy, preferably methoxy or ethoxy,
(C.sub.1-C.sub.4)haloalkoxy, nitro and cyano. Especially preferred
in this context are the substituents methyl, methoxy and
chlorine.
[0060] Mono- or disubstituted amino is a chemically stable radical
selected from the group consisting of substituted amino radicals
which are N-substituted by, for example, one or two identical or
different radicals selected from the group consisting of alkyl,
alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino,
acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles;
preferred in this context are alkyl radicals having 1 to 4 carbon
atoms; aryl is preferably phenyl or substituted phenyl in this
context; acyl is as defined further below, preferably
(C.sub.1-C.sub.4)alkanoyl. This also applies analogously to
substituted hydroxylamino or hydrazino.
[0061] Unsubstituted or substituted phenyl is preferably phenyl
which is unsubstituted or mono- or polysubstituted, preferably up
to trisubstituted, by identical or different radicals selected from
the group consisting of halogen, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)haloalkoxy and nitro, for example o-, m- and
p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and
4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and
2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
[0062] An acyl radical is, in a broad sense, the radical of an
organic acid which is formed formally by removing an OH group, for
example the radical of a carboxylic acid and radicals of acids
derived therefrom, such as thiocarboxylic acid, unsubstituted or
N-substituted iminocarboxylic acids or the radical of carbonic
monoesters, unsubstituted or N-substituted carbamic acid, sulfonic
acids, sulfinic acids, phosphonic acids, and phosphinic acids. Acyl
is, for example, formyl, alkylcarbonyl such as
[(C.sub.1-C.sub.4)alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl,
phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl,
N-alkyl-1-iminoalkyl and other radicals of organic acids. In this
context, the radicals can be even further substituted in each of
the alkyl or phenyl moieties, for example in the alkyl moiety by
one or more radicals selected from the group consisting of halogen,
alkoxy, phenyl and phenoxy; examples of substituents in the phenyl
moiety are the substituents which have already been mentioned
further above in general for substituted phenyl. Acyl in the
narrower sense is, for example, the radical of an alkanoic acid,
alkenoic acid, alkynoic acid, arylcarboxylic acid (for example
benzoyl), alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,
aryloxycarbonyl, alkylsulfonyl or alkysulfinyl; in an even narrower
sense, acyl is a radical of an alkanoic acid, for example a
(C.sub.1-C.sub.24)alkanoic acid, preferably
(C.sub.1-C.sub.18)alkanoic acid, in particular
(C.sub.1-C.sub.12)alkanoic acid, very especially
(C.sub.1-C.sub.6)alkanoic acid such as formyl, acetyl or
propionyl.
[0063] By combination of variables the generic formulae may
formally define instable functional groups, e.g. the carbamyl
radical or the hydroxy carbonyloxy radical, which are instable in
neutral or acidic aqueous medium and which thus are not preferred
or are used by way of their stable salts or degradation products
only, respectively.
[0064] Subject matter of the invention are all stereoisomers which
are encompassed by formula (I), and their mixtures. Such compounds
of the formula (I) contain one or more asymmetric carbon atoms or
else double bonds which are not stated specifically in the formula
(I). The possible stereoisomers which are defined by their specific
spatial form, such as enantiomers, diastereomers, Z- and E-isomers,
are all encompassed by formula (I) and can be obtained by customary
methods from mixtures of the stereoisomers, or else be prepared by
stereoselective reactions in combination with the use of
stereochemically pure starting materials.
[0065] Compounds of the stated formula (I) according to the
invention or their salts in which individual radicals have one of
the preferred meanings which have already been stated or are stated
hereinbelow, or in particular those in which one or more of the
preferred meanings which have already been stated or which are
stated hereinbelow are combined, are of particular interest, mainly
because of the more potent herbicidal action, better selectivity
and/or greater ease of preparation.
[0066] R.sup.1 is preferably phenyl, phenoxy, phenylthio,
phenylamino, N-phenyl-N-(C.sub.1-C.sub.4)alkylamino, where each of
the last-mentioned 5 radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, in
particular 6 to 15 carbon atoms. In this context, R.sup.1 is, in
particular, phenyl which is unsubstituted or substituted.
[0067] R.sup.1 is preferably also (C.sub.3-C.sub.9)cycloalkyl which
is unsubstituted or substituted by one or more radicals selected
from the group consisting of halogen, hydroxyl, amino, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino and di(C.sub.1-C.sub.4)alkylamino
and, inclusive of substituents, has 3 to 30 carbon atoms,
preferably 3 to 20 carbon atoms, in particular 3 to 15 carbon
atoms. In this context, R.sup.1 is, in particular,
(C.sub.3-C.sub.6)cycloalkyl which is unsubstituted or
substituted.
[0068] R.sup.1 is preferably also heterocyclyl which is
unsubstituted or substituted by one or more radicals selected from
the group consisting of halogen, hydroxyl, amino, nitro, formyl,
carboxyl, sulfonyl, cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)-alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.9)cycloalkyl,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, in
particular 2 to 15 carbon atoms.
[0069] In this context, and also in other radicals, heterocyclyl is
as defined further above in general terms or by preference.
[0070] In particular, heterocyclyl preferably is, in this context,
a heterocyclic radical having 3 to 7, in particular 3 to 6, ring
atoms and one hetero atom selected from the group consisting of N,
O and S, for example pyridyl, thienyl, furyl, pyrrolyl, oxiranyl,
oxetanyl, oxolanyl (=tetrahydrofuryl), oxanyl, pyrrolidyl,
piperidyl, or is a heterocyclic radical having two or three hetero
atoms selected from the group consisting of pyrimidinyl,
pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl,
thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl,
piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,
isoxazolidinyl, morpholinyl.
[0071] R.sup.1 is preferably also hydrogen or, in particular,
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkyny- l, (C.sub.1-C.sub.6)alkoxy or
(C.sub.1-C.sub.6)alkylthio, where each of the last-mentioned 5
radicals is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, cyano,
nitro, thiocyanato, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.2-C.sub.4)alkenyloxy,
(C.sub.2-C.sub.4)haloalkenyloxy, (C.sub.1-C.sub.4)alkylthio,
C.sub.1-C.sub.4)alkylsulfinyl, C.sub.1-C.sub.4)alkylsulfonyl,
(C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl and (C.sub.3-C.sub.6)cycloalkyl,
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino and
di(C.sub.1-C.sub.4)alkylamino, and phenyl and heterocyclyl, where
each of the two last-mentioned radicals is unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,
sulfonyl, cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.9)cycloalkyl,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl, and radicals of the formulae
R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-,
R'-Z-C(=Z')-O-, R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and
R'R"N--C(=Z')-NR'"-, where R', R" and R'" in each case
independently of one another are hydrogen or, in particular,
(C.sub.1-C.sub.4)alkyl, phenyl, phenyl(C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.6)cycloalkyl or
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.4)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.3-C.sub.6)cycloalkyl and, in the case of cyclic radicals,
also (C.sub.1-C.sub.4)alkyl and (C.sub.1-C.sub.4)haloalk- yl, and
where Z and Z' independently of one another are in each case an
oxygen or sulfur atom, and, inclusive of substituents, preferably
has 1 to 20 carbon atoms, in particular 1 to 15 carbon atoms,
[0072] R.sup.1 is furthermore preferably (C.sub.1-C.sub.4)alkyl
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulfonyl and (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, and
[0073] phenyl which is unsubstituted or substituted by one or more
radicals selected from the group consisting of halogen,
(C.sub.1-C.sub.4)alkyl and (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, amino, mono- and
di[(C.sub.1-C.sub.4)alkyl]am- ino, (C.sub.1-C.sub.4)alkanoylamino,
benzoylamino, nitro, cyano, [(C.sub.1-C.sub.4)alkyl]carbonyl,
formyl, carbamoyl, mono- and
di-[(C.sub.1-C.sub.4)alkyl]aminocarbonyl and
(C.sub.1-C.sub.4)alkylsulfon- yl, and
[0074] heterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ring
atoms selected from the group consisting of N, O and S, where the
ring is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen,
(C.sub.1-C.sub.4)alkyl and oxo, or
[0075] phenyl which is unsubstituted or substituted by one or more
radicals selected from the group consisting of halogen, hydroxyl,
amino, nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, in
particular 2 to 15 carbon atoms.
[0076] R.sup.1 is furthermore preferably (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, benzyl or
[(C.sub.3-C.sub.6)cycloalkyl]-(C.su- b.1-C.sub.2)alkyl, in
particular (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl or
[(C.sub.3-C.sub.6)cycloalkyl]methyl, very especially -CH.sub.3,
-CH.sub.2F, -CHF.sub.2, -CF.sub.3, -CH.sub.2Cl, -CHCl.sub.2,
-CCl.sub.3, -CH.sub.2Br, -CHBr.sub.2, -CH.sub.2CH.sub.3,
-CH.sub.2CH.sub.2F, -CF.sub.2CHF.sub.2, -CH.sub.2CH.sub.2Cl,
-CHFCH.sub.3, -CHFCH.sub.2CH.sub.3, -CH.sub.2CH.sub.2Br,
-CH(CH.sub.3).sub.2, -CF(CH.sub.3).sub.2, -C(CH.sub.3).sub.2Cl,
-CH.sub.2CH.sub.2CH.sub.2F, 1-5 -CH.sub.2CH.sub.2CH.sub.2Cl or
cyclopropylmethyl or 1-fluorocycloprop-1-yl.
[0077] Other preferred compounds (I) according to the invention are
those in which
[0078] R.sup.1 is aryl which is unsubstituted or substituted and,
inclusive of substituents, preferably has 6 to 30 carbon atoms, or
(C.sub.3-C.sub.9)cycloalkyl which is unsubstituted or substituted
and, inclusive of substituents, preferably has 3 to 30 carbon
atoms, or heterocyclyl which is unsubstituted or substituted and,
inclusive of substituents, preferably has 2 to 30 carbon atoms, or
is (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl or
(C.sub.2-C.sub.6)alkynyl,
[0079] where each of the last-mentioned 3 radicals is unsubstituted
or substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, cyano, nitro, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.2-C.sub.4)alkenyloxy, (C.sub.2-C.sub.4)haloalkenyloxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulfinyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, phenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, and radicals of the formulae R'-C(=Z')-,
R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-, R'-Z-C(=Z')-O-,
R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and R'R"N--C(=Z')-NR'"-, where
R', R" and R'" in each case independently of one another are
(C.sub.1-C.sub.6)alkyl, aryl, aryl-(C.sub.1-C.sub.6)alkyl,
(C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub- .6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and
where Z and Z' independently of one another are in each case an
oxygen or sulfur atom,
[0080] and, inclusive of substituents, preferably has 1 to 30
carbon atoms,
[0081] R.sup.1 is preferably also phenyl which is unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,
sulfo, cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.9)cycloalkyl,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, in
particular 6 to 15 carbon atoms.
[0082] Independently of the radicals R.sup.1, R.sup.3, R.sup.4,
L.sup.0, A.sup.1, A.sup.2 and (X).sub.n and preferably in
combination with preferred meanings of one or more of these
radicals, the following meanings of R.sup.2 are of particular
interest.
[0083] R.sup.2 is preferably (C.sub.3-C.sub.9)cycloalkyl which is
unsubstituted or substituted by one or more radicals selected from
the group consisting of the radicals A), B), C) and D), where
[0084] group A) consists of the radicals halogen, hydroxyl, amino,
nitro, formyl, carboxyl, aminocarbonyl, sulfo, cyano, thiocyanato
and oxo,
[0085] group B) consists of the radicals (C.sub.1-C.sub.6)alkyl,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkylthio,
mono(C.sub.1-C.sub.6)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.3-C.sub.9)cycloalkyl, (C.sub.4-C.sub.9)cycloalkenyl,
(C.sub.1-C.sub.6)alkylidene, (C.sub.4-C.sub.9)cycloalkylidene,
radicals of the formulae R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-,
R'R"N--C(=Z')-, R'-Z-C(=Z')-O-, R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"-
and R'R"N--C(=Z')-NR'"-, where R', R" and R'" in each case
independently of one another are hydrogen or, in particular,
(C.sub.1-C.sub.6)alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)alkyl,
(C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl and where Z and
Z' independently of one another are in each case an oxygen or
sulfur atom,
[0086] group C) consists of radicals as defined for group B), but
where each radical is substituted by one or more radicals selected
from the group consisting of halogen, hydroxyl, amino, nitro,
formyl, carboxyl, sulfo, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, (C.sub.4-C.sub.9)cycloalkylene
(C.sub.4-C.sub.9)cycloalkylidene, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl, phenyl, phenoxy, phenylthio,
phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and
heterocyclylamino,
[0087] where each of the last-mentioned 21 radicals is
unsubstituted or substituted by one or more radicals selected from
the group consisting of halogen, nitro, cyano,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthi- o,
(C.sub.1-C.sub.4)haloalkoxy, formyl, (C.sub.1-C.sub.4)alkylcarbonyl
and (C.sub.1-C.sub.4)alkoxycarbonyl and, in the case of cyclic
radicals, also (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl
and (C.sub.1-C.sub.6)alkylidene, and, in the case of cyclic
radicals, also (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl
and (C.sub.1-C.sub.6)alkylidene, and
[0088] group D) consists of divalent or trivalent aliphatic bridges
having 1 to 6, preferably 1 to 4, carbon atoms which, in the case
of divalent bridges, connect two and, in the case of trivalent
bridges, three carbon atoms of the cyclic skeleton and the radical
R.sup.2 thus constitutes the radical of a bicyclic or tricyclic
system, where each of the bridges is unsubstituted or substituted
by one or more substituents selected from the group consisting of
halogen, nitro, cyano, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy, formyl,
(C.sub.1-C.sub.4)alkylcarbonyl, (C.sub.1-C.sub.4)alkoxycarbonyl and
oxo,
[0089] and where R.sup.2, inclusive of substituents, preferably has
3 to 20 carbon atoms, in particular 3 to 15 carbon atoms. Preferred
(C.sub.3-C.sub.9)cycloalkyl radicals are, in this context,
cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, in particular
cyclopropyl, cyclobutyl or cyclopentyl.
[0090] R.sup.2 is preferably also (C.sub.4-C.sub.9)cycloalkenyl
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of the radicals A), B), C) and
D), as are defined as radicals for the case
R.sup.2=(C.sub.3-C.sub.9)cycloalkyl, and, inclusive of
substituents, preferably has 4 to 20 carbon atoms, in particular 4
to 15 carbon atoms.
[0091] Preferred (C.sub.4-C.sub.9)cycloalkenyl radicals are
1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl
and 3-cyclopentenyl.
[0092] R.sup.2 is preferably also heterocyclyl which is
unsubstituted or substituted by one or more radicals selected from
the group consisting of the radicals A), B), C) and D), as are
defined as radicals for the case
R.sup.2=(C.sub.3-C.sub.9)cycloalkyl.
[0093] In this context, heterocyclyl is preferably a heterocyclic
radical having 3 to 6 ring atoms and one heteroring atom, in
particular, a radical selected from the group consisting of
pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, 2-oxetanyl,
3-oxetanyl, oxolanyl (=tetrahydrofuryl), pyrrolidyl, piperidyl, in
particular oxiranyl, 2-oxetanyl, 3-oxetanyl or oxolanyl, or is a
heterocyclic radical having two or three hetero atoms, for example
pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl,
thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl,
piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,
isoxazolidinyl or morpholinyl.
[0094] R.sup.2 is preferably also phenyl which is unsubstituted or
substituted by one or more radicals selected from the group of the
radicals A), B) and C) as are defined as radicals for
R.sup.2=(C.sub.3-C.sub.9)cycloalkyl.
[0095] Inclusive of substituents, R.sup.2 preferably has up to 20
carbon atoms, in particular up to 15 carbon atoms, very especially
up to 10 carbon atoms.
[0096] R.sup.2 is preferably (C.sub.3-C.sub.9)cycloalkyl which is
unsubstituted or substituted by one or more radicals selected from
the group consisting of the radicals A), B), C) and D),
[0097] where
[0098] group A) consists of the radicals halogen, hydroxyl, nitro,
formyl, aminocarbonyl, cyano and thiocyanato,
[0099] group B) consists of the radicals (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.3-C.sub.6)cycloalkyl, (C.sub.4-C.sub.6)cycloalkenyl,
(C.sub.1-C.sub.4)alkylidene, (C.sub.4-C.sub.6)cycloalkylidene,
radicals of the formulae R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-,
R'R"N--C(=Z')-, R'-Z-C(=Z')-O-, R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"-
and R'R"N--C(=Z')-NR'"-, where R', R" and R'" in each case
independently of one another are hydrogen or, in particular,
(C.sub.1-C.sub.4)alkyl, phenyl, phenyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.6)cycloalkyl or
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.6)alkyl and where Z and
Z' independently are in each case one oxygen or sulfur atom,
[0100] group C) consists of radicals as shown for group B), but
where each radical is substituted by one or more radicals selected
from the group consisting of halogen, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalko- xy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.6)cycloalkyl,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl, phenyl, phenoxy, phenylthio,
phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and
heterocyclylamino,
[0101] where each of the last-mentioned 8 radicals is unsubstituted
or has one or more substituents selected from the group consisting
of halogen, nitro, cyano, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylcarbonyl and (C.sub.1-C.sub.4)alkoxycarbonyl,
and
[0102] group D) consists of divalent aliphatic bridges which
connect two carbon atoms of the cyclic skeleton and the radical
R.sup.2 thus represents the radical of a bicyclic system, for
example bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl,
bicyclo[2.1.0]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl or
bicyclo[2.1.0]pentan-5-yl, where each of the bridges is
unsubstituted or substituted by one or more substituents selected
from the group consisting of halogen, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylcarbonyl, (C.sub.1-C.sub.4)alkoxycarbonyl and
oxo.
[0103] R.sup.2 is especially preferably (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
(C.sub.1-C.sub.4)alkylidene, mono(C.sub.1-C.sub.4)alkylamino and
di(C.sub.1-C.sub.4)alkylamino, or is heterocyclyl or phenyl, where
each of the last-mentioned two radicals is unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,
sulfonyl, cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.6)cycloalkyl,
heterocyclyl having 3 to 6 ring atoms,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl.
[0104] Independently of the radicals R.sup.1, R.sup.2, R.sup.4,
A.sup.1, A.sup.2, L.sup.0 and (X).sub.n, and preferably in
combination with preferred meanings of one or more of these
radicals, the following meanings of R.sup.3 are of particular
interest: 4
[0105] where the radicals R.sup.5 to R.sup.17 are defined further
below.
[0106] Also of particular interest are compounds 5
[0107] in which
[0108] R.sup.6 and R.sup.7 together with the nitrogen atom of the
group NR.sup.6R.sup.7,
[0109] R.sup.7 and OR.sup.8 together with the nitrogen atom of the
group NOR.sup.8R.sup.7,
[0110] R.sup.7 and SR.sup.8 together with the nitrogen atom of the
group NSR.sup.8R.sup.7,
[0111] R.sup.10 and R.sup.11 together with the nitrogen atom of the
group NR.sup.10R.sup.11,
[0112] OR.sup.12 and OR.sup.13 or SR.sup.12 and SR.sup.13 together
with the carbon atom of the 6
[0113] respectively,
[0114] OR.sup.9 and R.sup.14 or SR.sup.9 and R.sup.14 together with
the carbon atom of the groups 7
[0115] respectively,
[0116] R.sup.14 and R.sup.15 together with the carbon atom of the
group 8
[0117] R.sup.5 and R.sup.7 together with the atom group 9
[0118] R.sup.5 and R.sup.17 together with the carbon atom of the
group 10
[0119] R.sup.5 and R.sup.16 together with the atom group 11
[0120] R.sup.7 and R.sup.10 together with the atom group 12
[0121] in each case independently of one another form a carbocyclic
or heterocyclic ring having 3 to 7 ring atoms and 1 to 6 hetero
atoms, where the optional further hetero ring atoms are selected
from the group consisting of N, O and S and the carbocyclic or
heterocyclic ring is in each case unsubstituted or substituted,
[0122] the radicals R.sup.5 to R.sup.17 being defined
hereinbelow.
[0123] In the above formulae for atom groups, the symbol for a
double bond "=" which has substituents on one side only (unilateral
double bond) denotes the bonding site of a double bond (.dbd.a free
double bond, synonymous with the binding sites of an ylidene
radical) and not the abbreviated form of vinyl.
[0124] R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10,
R.sup.11, R.sup.14, R.sup.15, R.sup.16, R.sup.17 in the above
formulae independently of one another are
[0125] hydrogen, aryl which is unsubstituted or substituted and,
inclusive of substituents, preferably has 6 to 30 carbon atoms, or
(C.sub.3-C.sub.9)cycloalkyl which is unsubstituted or substituted
and, inclusive of substituents, preferably has 3 to 30 carbon
atoms, or heterocyclyl which is unsubstituted or substituted and,
inclusive of substituents, preferably has 2 to 30 carbon atoms, or
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl or
(C.sub.2-C.sub.6)alkynyl,
[0126] where each of the last-mentioned 3 radicals is unsubstituted
or substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, cyano, nitro, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.2-C.sub.4)alkenyloxy, (C.sub.2-C.sub.4)haloalkenyloxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulfinyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, phenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, and radicals of the formulae R'-C(=Z'),
R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-, R'-Z-C(=Z')-O-,
R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and R'R"N--C(=Z')-NR'"-,
[0127] where R', R" and R'" in each case independently of one
another are hydrogen or, in particular, (C.sub.1-C.sub.6)alkyl,
aryl, aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and
where Z and Z' independently of one another are in each case an
oxygen or sulfur atom,
[0128] and, inclusive of substituents, preferably has 1 to 30
carbon atoms.
[0129] R.sup.12, R.sup.13 in each case independently of one another
are aryl which is unsubstituted or substituted and, inclusive of
substituents, preferably has 6 to 30 carbon atoms, or
(C.sub.3-C.sub.9)cycloalkyl which is unsubstituted or substituted
and, inclusive of substituents, preferably has 3 to 30 carbon
atoms, or heterocyclyl which is unsubstituted or substituted and,
inclusive of substituents, preferably has 2 to 30 carbon atoms, or
are (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl or
(C.sub.2-C.sub.6)alkynyl,
[0130] where each of the last-mentioned 3 radicals is unsubstituted
or substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, cyano, nitro, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.2-C.sub.4)alkenyloxy, (C.sub.2-C.sub.4)haloalkenyloxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulfinyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl
which is unsubstituted or substituted, phenyl which is
unsubstituted or substituted, heterocyclyl which is unsubstituted
or substituted, and radicals of the formulae R'-C(=Z')-,
R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-, R'-Z-C(=Z')O-,
R'R"N--C(=Z')-Z-, R'-Z-C(=Z')NR"- and R'R"N--C(=Z')-NR"-,
[0131] where R', R" and R'" in each case independently of one
another are hydrogen or, in particular, (C.sub.1-C.sub.6)alkyl,
aryl, aryl-(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.9)cycloalkyl or
(C.sub.3-C.sub.9)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted and
where Z and Z' independently of one another are in each case one
oxygen or sulfur atom,
[0132] and, inclusive of substituents, preferably has 1 to 30
carbon atoms.
[0133] Preferably, the radicals R.sup.5, R.sup.6, R.sup.7, R.sup.8,
R.sup.9, R.sup.10, R.sup.11, R.sup.14, R.sup.15, R.sup.16, R.sup.17
independently of one another are hydrogen.
[0134] Preferably, the radicals R.sup.5, R.sup.6, R.sup.7, R.sup.8,
R.sup.9, R.sup.10, R.sup.11, R.sup.14, R.sup.15, R.sup.16, R.sup.17
in each case independently of one another are also phenyl which is
unsubstituted or substituted by one or more radicals selected from
the group consisting of halogen, hydroxyl, amino, nitro, formyl,
carboxyl, sulfo, cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.9)cycloalkyl,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, in
particular 6 to 15 carbon atoms.
[0135] Preferably, the radicals R.sup.5, R.sup.6, R.sup.7, R.sup.8,
R.sup.9, R.sup.10, R.sup.11, R.sup.14, R.sup.15, R.sup.16, R.sup.17
in each case independently of one another are also
(C.sub.3-C.sub.9)cycloalk- yl which is unsubstituted or substituted
by one or radicals selected from the group consisting of halogen,
hydroxyl, amino, cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino and
di(C.sub.1-C.sub.4)alkylamino and, inclusive of substituents, has 3
to 30 carbon atoms, preferably 3 to 20 carbon atoms, in particular
3 to 15 carbon atoms.
[0136] Preferably, the radicals R.sup.5, R.sup.6, R.sup.7, R.sup.8,
R.sup.9, R.sup.10, R.sup.11, R.sup.14, R.sup.15, R.sup.16, R.sup.17
in each case independently of one another are also heterocyclyl
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, in
particular 2 to 15 carbon atoms.
[0137] Here and also in other radicals, heterocyclyl preferably is
a heterocyclic radical having 3 to 7, in particular 3 to 6, ring
atoms and one hetero atom selected from the group consisting of N,
O and S, for example pyridyl, thienyl, furyl, pyrrolyl, oxiranyl,
oxetanyl, oxolanyl (=tetrahydrofuryl), oxanyl, pyrrolidyl,
piperidyl, or is a heterocyclic radical having two or three hetero
atoms selected from the group consisting of pyrimidinyl,
pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl,
thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl,
piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,
isoxazolidinyl, morpholinyl.
[0138] R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10,
R.sup.11, R.sup.14, R.sup.15, R.sup.16, R.sup.17 independently of
one another are preferably also (C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl or (C.sub.2-C.sub.6)alkynyl, where each of
the last-mentioned 3 radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, cyano, nitro, thiocyanato, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.2-C.sub.4)alkenyloxy,
(C.sub.2-C.sub.4)haloalkenyloxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl,
(C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.6)cycloalkyl
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino and
di(C.sub.1-C.sub.4)alkylamino, phenyl and heterocyclyl, where each
of the two last-mentioned radicals is unsubstituted or substituted
by one or more radicals selected from the group consisting of
halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl, and radicals of the formulae
R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z'), R'R-N--C(=Z')-,
R'-Z-C(=Z')-O-, R'R"N--C(=Z')-Z-, R'-Z-C(=Z')NR"- and
R'R"N--C(=Z')-N R'"-,
[0139] where R', R" and R'" in each case independently of one
another are hydrogen or, in particular, (C.sub.1-C.sub.4)alkyl,
phenyl, phenyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl
or (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.4)alkyl, where each
of the 5 last-mentioned radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.3-C.sub.6)cycloalkyl and, in the case of cyclic radicals,
also (C.sub.1-C.sub.4)alkyl and (C.sub.1-C.sub.4)haloalk- yl, and
where Z and Z' independently of one another are in each case one
oxygen or sulfur atom, and, inclusive of substituents, preferably
has 1 to 20 carbon atoms, in particular 1 to 15 carbon atoms,
[0140] R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10,
R.sup.11, R.sup.14, R.sup.15, R .sup.16, R.sup.17 in each case
independently of one another are preferably (C.sub.1-C.sub.4)alkyl
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.3-C.sub.9)cycloalkyl which
is unsubstituted or substituted and phenyl which is unsubstituted
or substituted by one or more radicals selected from the group
consisting of halogen, (C.sub.1-C.sub.4)alkyl and
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio, amino,
mono- and di[(C.sub.1-C.sub.4)alkyl]am- ino,
(C.sub.1-C.sub.4)alkanoylamino, benzoylamino, nitro, cyano,
[(C.sub.1-C.sub.4)alkyl]carbonyl, formyl, carbamoyl, mono- and
di[(C.sub.1-C.sub.4)alkyl]aminocarbonyl and
(C.sub.1-C.sub.4)alkylsulfony- l, and heterocyclyl having 3 to 6
ring atoms and 1 to 3 hetero ring atoms selected from the group
consisting of N, O and S, the ring being unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, (C.sub.1-C.sub.4)alkyl and oxo, or phenyl
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, in
particular 2 to 15 carbon atoms.
[0141] R.sup.12, R.sup.13 in each case independently of one another
are preferably also phenyl which is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, in
particular 6 to 15 carbon atoms.
[0142] R.sup.12, R.sup.13 in each case independently of one another
are preferably also (C.sub.3-C.sub.9)cycloalkyl which is
unsubstituted or substituted by one or more radicals selected from
the group consisting of halogen, hydroxyl, amino, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino and di(C.sub.1-C.sub.4)alkylamino
and, inclusive of substituents, has 3 to 30 carbon atoms,
preferably 3 to 20 carbon atoms, in particular 3 to 15 carbon
atoms.
[0143] R.sup.12, R.sup.13 in each case independently of one another
are preferably also heterocyclyl which is unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,
sulfonyl, cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.9)cycloalkyl,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, in
particular 2 to 15 carbon atoms.
[0144] Here and also in other radicals, heterocyclyl is preferably
a heterocyclic radical having 3 to 7, in particular 3 to 6, ring
atoms and one hetero atom selected from the group consisting of N,
O and S, for example pyridyl, thienyl, furyl, pyrrolyl, oxiranyl,
oxetanyl, oxolanyl (=tetrahydrofuryl), oxanyl, pyrrolidyl,
piperidyl, or is a heterocyclic radical having two or three hetero
atoms selected from the group consisting of pyrimidinyl,
pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl,
thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl,
piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,
isoxazolidinyl, morpholinyl.
[0145] R.sup.12, R.sup.13 in each case independently of one another
are preferably also (C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkenyl or (C.sub.2-C.sub.6)alkynyl, where each of
the last-mentioned 3 radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, cyano, nitro, thiocyanato, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.2-C.sub.4)alkenyloxy,
(C.sub.2-C.sub.4)haloalkenyloxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)alkylsulfinyl, (C.sub.1-C.sub.4)alkylsulfonyl,
(C.sub.1-C.sub.4)haloalkylsulfinyl,
(C.sub.1-C.sub.4)haloalkylsulfonyl, (C.sub.3-C.sub.6)cycloalkyl
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino and
di(C.sub.1-C.sub.4)alkylamino, or phenyl and heterocyclyl, where
each of the two last-mentioned radicals is unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,
sulfonyl, cyano, thiocyanato, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.9)cycloalkyl,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl, and radicals of the formulae
R'-C(=Z')-, R'-C(=Z')-Z-, R'-Z-C(=Z')-, R'R"N--C(=Z')-,
R'-Z-C(=Z')-O-, R'R"N--C(=Z')-Z-, R'-Z-C(=Z')-NR"- and
R'R"N--C(=Z')NR'"-,
[0146] where R', R" and R'" in each case independently of one
another are hydrogen or, in particular, (C.sub.1-C.sub.4)alkyl,
phenyl, phenyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl
or (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.4)alkyl, where each
of the 5 last-mentioned radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.2-C.sub.4)alkenyl, (C.sub.2-C.sub.4)alkynyl,
(C.sub.3-C.sub.6)cycloalkyl and, in the case of cyclic radicals,
also (C.sub.1-C.sub.4)alkyl and (C.sub.1-C.sub.4)haloalk- yl, and
where Z and Z' independently of one another are in each case one
oxygen or sulfur atom, and, inclusive of substituents, preferably
has 1 to 20 carbon atoms, in particular 1 to 15 carbon atoms.
[0147] R.sup.12, R.sup.13 in each case independently of one another
are preferably (C.sub.1-C.sub.4)alkyl which is unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)alkylsulfonyl,
(C.sub.3-C.sub.9)cycloalkyl which is unsubstituted or substituted
and phenyl which is unsubstituted or substituted by one or more
radicals selected from the group consisting of halogen,
(C.sub.1-C.sub.4)alkyl and (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, amino, mono- and
di[(C.sub.1-C.sub.4)alkyl]am- ino, (C.sub.1-C.sub.4)alkanoylamino,
benzoylamino, nitro, cyano, [(C.sub.1-C.sub.4)alkyl]carbonyl,
formyl, carbamoyl, mono- and
di-[(C.sub.1-C.sub.4)alkyl]aminocarbonyl and
(C.sub.1-C.sub.4)alkylsulfon- yl, and heterocyclyl having 3 to 6
ring atoms and 1 to 3 hetero ring atoms selected from the group
consisting of N, O and S, where the ring is unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, (C.sub.1-C.sub.4)alkyl and oxo, or phenyl
which is unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl and
(C.sub.1-C.sub.4)haloalkylsulfonyl and, inclusive of substituents,
has 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, in
particular 2 to 15 carbon atoms.
[0148] Independently of the radicals R.sup.1, R.sup.2, R.sup.3,
L.sup.0, A.sup.1, A.sup.2 and (X).sub.n, and preferably in
combination with preferred meanings of one or more of these
radicals, the following meanings of R.sup.4 are of particular
interest:
[0149] R.sup.4 is, for example, a radical of the formula
-B.sup.1-D.sup.1, where B.sup.1 and D.sup.1 are preferably as
defined further below.
[0150] R.sup.4 is preferably hydrogen, (C.sub.1-C.sub.4)alkyl,
phenyl or (C.sub.3-C.sub.6)cycloalkyl, where each of the 3
last-mentioned radicals is unsubstituted or substituted by one or
more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfonyl
and, in the case of cyclic radicals, also (C.sub.1-C.sub.4)alkyl
and (C.sub.1-C.sub.4)haloalkyl, or formyl,
[(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl or
di(C.sub.1-C.sub.4)alkylaminocarbonyl; in particular hydrogen,
methyl, ethyl, n-propyl or isopropyl; especially preferably
hydrogen.
[0151] Independently of the radicals R.sup.1 to R.sup.4, A.sup.1,
A.sup.2 and (X).sub.n, and preferably in combination with preferred
meanings of one or more of these radicals, the following meanings
of L.sup.0 are of particular interest:
[0152] L.sup.0 is a direct bond or oxygen.
[0153] Independently of the radicals R.sup.1 to R.sup.4, L.sup.0,
A.sup.2 and (X).sub.n and preferably in combination with preferred
meanings of one or more of these radicals, the following meanings
of A.sup.1 are of particular interest:
[0154] A.sup.1 is, for example, straight-chain alkylene having 1 to
5 carbon atoms or straight-chain alkenylene or alkynylene having in
each case 2 to 5 carbon atoms, where each of the three
last-mentioned diradicals is unsubstituted or substituted by one or
more radicals selected from the group consisting of halogen, nitro,
cyano, thiocyanato and a radical of the formula -B.sup.2-D.sup.2,
in which
[0155] B.sup.2 is a direct bond or a divalent group of the formulae
-O-, -SO.sub.2-, -CO-, -O--CO-, -NR.sup.0-, -NR.sup.0-CO-,
-CO-NR.sup.0-, -O--CO-NR.sup.0- or -N'R-CO--O-, in which
[0156] R.sup.O independently of one another are in each case
hydrogen, (C.sub.1-C.sub.4)alkyl, phenyl,
phenyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl or
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub- .4)alkyl, where each of
the last-mentioned 5 radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfonyl
and, in the case of cyclic radicals, also (C.sub.1-C.sub.4)alkyl
and (C.sub.1-C.sub.4)haloalkyl.
[0157] A.sup.1 is preferably a radical of the formula
[0158] -CH.sub.2-, -CH.sub.2CH.sub.2-, -CH.sub.2CH.sub.2CH.sub.2-,
-CH.sub.2CH.sub.2CH.sub.2CH.sub.2- or
-CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH- .sub.2-,
[0159] which radical is unsubstituted. Also preferred is one of the
above radicals which is substituted by one or more of the
abovementioned radicals -B.sup.2-D.sup.2. A.sup.1 is especially
preferably a radical of the formula -CH.sub.2CH.sub.2- or
-CH.sub.2CH.sub.2CH.sub.2-, which radical is unsubstituted or
substituted by one or two radicals of the formula hydroxyl,
(C.sub.1-C.sub.4)alkyl or (C.sub.1-C.sub.4)alkoxy.
[0160] Independently of the radicals R.sup.1 to R.sup.4, L.sup.0,
A.sup.1 and (X).sub.n and preferably in combination with preferred
meanings of one or more of these radicals, the following meanings
of A.sup.2 are of particular interest:
[0161] A.sup.2 is preferably
[0162] a direct bond or a group of the formula -CH.sub.2-,
-CH.sub.2CH.sub.2-, -CH.sub.2CH.sub.2CH.sub.2- or
-CH.sub.2CH.sub.2CH.sub- .2CH.sub.2-, where each of the 4
last-mentioned diradicals is unsubstituted or substituted by one or
more radicals selected from the group consisting of halogen, nitro,
cyano, thiocyanato and radicals of the formula -B.sup.3-D.sup.3, or
a divalent radical of the formula V.sup.1, V.sup.2, V.sup.3,
V.sup.4 or V.sup.5,
[0163] -CR.sup.aR.sup.b-W*-CR.sup.cR.sup.d-(V.sup.1)
[0164] -CR.sup.aR.sup.b-W*-CR.sup.cR.sup.d-CR.sup.eR.sup.f-(V2)
[0165] -CR.sup.aR.sup.b-CR.sup.cR.sup.d-W*-CR.sup.eR.sup.f-(V3)
[0166] -CR.sup.aR.sup.b-CR.sup.cR.sup.d-W*-(V.sup.4)
[0167] -CR.sup.aR.sup.b-W*- (V.sup.5),
[0168] where each of the radicals R.sup.a to R.sup.f in each case
independently of one other is hydrogen, halogen, nitro, cyano,
thiocyanato or a radical of the formula -B.sup.4-D.sup.4,
[0169] W* is in each case O, S or a group of the formula
N(B.sup.5-D.sup.5), and B.sup.3, B.sup.4, B.sup.5, D.sup.3, D.sup.4
and D.sup.5 are as defined below.
[0170] A.sup.2 is especially preferably a direct bond or a group of
the formula
-CH.sub.2-, -CH.sub.2CH.sub.2-, -CH.sub.2CH.sub.2CH.sub.2-,
-CH.sub.2CH.sub.2CH.sub.2CH.sub.2,
-CH.sub.2-0-CH.sub.2-, -CH.sub.2-O-CH.sub.2-CH.sub.2-,
-CH.sub.2-CH.sub.2-O-CH.sub.2-,
-CH.sub.2-S-CH.sub.2-, -CH.sub.2-S-CH.sub.2-CH.sub.2-,
-CH.sub.2-CH.sub.2-S-CH.sub.2-,
-CH.sub.2-NH-CH.sub.2-, -CH.sub.2-NH-CH.sub.2-CH.sub.2-,
-CH.sub.2-CH.sub.2-NH-CH.sub.2-,
-CH.sub.2-N(CH.sub.3)-CH.sub.2-, -CH.sub.2-N(CH.sub.3)-CH.sub.2-CH2
or -CH.sub.2-CH.sub.2-N(CH.sub.3)-CH.sub.2-.
[0171] B.sup.1 and B.sup.5 are preferably in each case
independently of one another a direct bond a divalent group of the
formulae -C(=Z*)-, -C(=Z*)-Z**-, -C(=Z*)-NH- or -C(=Z*)-NR*-, where
Z*=O or S, Z**=O or S and R*=(C.sub.1-C.sub.4)alkyl, phenyl,
phenyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl or
(C.sub.3-C.sub.6)cycloalkyl(C.sub.1-C.sub.- 4)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted,
preferably unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
nitro, formyl, carboxyl, sulfo, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfonyl
and, in the case of cyclic radicals, also (C.sub.1-C.sub.4)alkyl
and (C.sub.1-C.sub.4)haloalkyl.
[0172] B.sup.1 and B.sup.5 are also preferably independently of
another a direct bond or a divalent group of the formulae -C(=Z*)-,
-C(=Z*)-Z**-, -C(=Z*)-NH- or -C(=Z*)-NR*-, where Z* =O or S, Z**=O
or S and
[0173] R*=(C.sub.1-C.sub.4)alkyl, phenyl,
phenyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl or
(C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub- .4)alkyl, where each of
the 5 last-mentioned radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, formyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl and, in the case of cyclic
radicals, also (C.sub.1-C.sub.4)alkyl and
(C.sub.1-C.sub.4)haloalkyl, in particular R*=(C.sub.1-C.sub.4)alkyl
or (C.sub.3-C.sub.6)cycloalkyl or in particular R*=phenyl or
phenyl-(C.sub.1-C.sub.4)alkyl, where each of the two last-mentioned
radicals is unsubstituted or substituted in the phenyl moiety or by
one or more radicals selected from the group consisting of halogen,
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy or (C.sub.1-C.sub.4)haloalkoxy.
[0174] B.sup.2, B.sup.3 and B.sup.4 are preferably in each case
independently of one another a direct bond or a divalent group of
the formulae -O-, -S(O).sub.p-, -S(O).sub.p-O-, -O--S(O).sub.p-,
-CO-, -O--CO-, -CO--O-, -S--CO-, -CO--S-, -S--CS-, -CS--S-,
-O--CO--O-, -NR.sup.0-, -O-NR.sup.0-, -NR.sup.0-O-, -NR.sup.0-CO-,
-CO-NR.sup.0-, -O--CO-NR.sup.0- or -NR.sup.0-CO--O-, where p is the
integer 0, 1 or 2 and R.sup.0=hydrogen, (C.sub.1-C.sub.4)alkyl,
phenyl, phenyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl
or (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.4)alkyl, where each
of the 5 last-mentioned radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano,
thiocyanato, (C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)al- kylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfonyl
and, in the case of cyclic radicals, also (C.sub.1-C.sub.4)alkyl
and (C.sub.1-C.sub.4)haloalkyl, and in particular R.sup.0=hydrogen,
(C.sub.1-C.sub.4)alkyl or (C.sub.3-C.sub.6)cycloalkyl or in
particular R.sup.0=phenyl or phenyl-(C.sub.1-C.sub.4)alkyl, where
each of the two last-mentioned radicals is unsubstituted or
substituted in the phenyl moiety by one or more radicals selected
from the group consisting of halogen, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy or
(C.sub.1-C.sub.4)haloalkoxy.
[0175] B.sup.2, B.sup.3 and B.sup.4 are also preferably
independently of one another
[0176] a direct bond or a
[0177] divalent group of the formulae -O-, -S(O).sub.p-, -CO-,
-O--CO-, -CO--O-, -S--CO-, -CO--S-, -NR.sup.0-, -NR.sup.0-CO-,
-CO-NR.sup.0-, -O--CO-NR.sup.0- or -NR.sup.0-CO--O-, where p is the
integer 0, 1 or 2, in particular 0 or 2, and R.sup.0 has the
abovementioned meaning, very especially H or
(C.sub.1-C.sub.4)alkyl.
[0178] D.sup.1, D.sup.2, D.sup.3, D.sup.4 and D.sup.5 preferably
independently of one another are hydrogen, (C.sub.1-C.sub.6)alkyl,
phenyl, phenyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl
or (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.6)alkyl, where each
of the 5 last-mentioned radicals is unsubstituted or substituted,
preferably unsubstituted or substituted by one or more radicals
selected from the group consisting of halogen, hydroxyl, amino,
nitro, formyl, carboxyl, sulfo, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
(C.sub.1-C.sub.4)alkylsulfonyl, (C.sub.1-C.sub.4)haloalkylsulfonyl
and, in the case of cyclic radicals, also (C.sub.1-C.sub.4)alkyl
and (C.sub.1-C.sub.4)haloalkyl.
[0179] D.sup.1, D.sup.2, D.sup.3, D.sup.4 and D.sup.5 also
preferably independently of one another are (C.sub.1-C.sub.4)alkyl,
phenyl, phenyl-(C.sub.1-C.sub.4)alkyl, (C.sub.3-C.sub.6)cycloalkyl
or (C.sub.3-C.sub.6)cycloalkyl-(C.sub.1-C.sub.4)alkyl, where each
of the 5 last-mentioned radicals is unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen,
hydroxyl, amino, formyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)haloalkoxy, (C.sub.1-C.sub.4)alkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.9)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocarbonyl and, in the case of cyclic
radicals, also (C.sub.1-C.sub.4)alkyl and
(C.sub.1-C.sub.4)haloalkyl, and, in particular, they are
[0180] (C.sub.1-C.sub.4)alkyl or (C.sub.3-C.sub.6)cycloalkyl or
phenyl or phenyl-(C.sub.1-C.sub.4)alkyl, where each of the two
last-mentioned radicals is unsubstituted or substituted in the
phenyl moiety by one or more radicals selected from the group
consisting of halogen, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)alkoxy or
(C.sub.1-C.sub.4)haloalkoxy.
[0181] Independently of the radicals R.sup.1 to R.sup.4, L.sup.0,
A.sup.1 and A.sup.2 and preferably in combination with preferred
meanings of one or more of these radicals, the following meanings
of (X).sub.n are of particular interest:
[0182] (X).sub.n is n substituents X, where X preferably in each
case independently of one another are halogen, hydroxyl, amino,
nitro, formyl, carboxyl, cyano, thiocyanato, aminocarbonyl or
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.2-C.sub.4)alkenyl,
(C.sub.2-C.sub.4)alkynyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylaminocar- bonyl,
N-(C.sub.1-C.sub.6)alkanoylamino or
N-(C.sub.1-C.sub.4)alkanoyl-N-(- C.sub.1-C.sub.4)alkylamino,
[0183] where each of the last-mentioned 13 radicals is
unsubstituted or substituted, preferably unsubstituted or
substituted by one or more radicals selected from the group
consisting of halogen, hydroxyl, amino, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkylamino, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkylamino, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
[0184] mono(C.sub.1-C.sub.4)alkylaminocarbonyl,
di(C.sub.1-C.sub.4)alkylam- inocarbonyl, phenyl, phenoxy,
phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy,
heterocyclylthio and heterocyclylamino,
[0185] where each of the last-mentioned 8 radicals is unsubstituted
or has one or more substituents selected from the group consisting
of halogen, nitro, cyano, (C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylthio,
(C.sub.1-C.sub.4)haloalkyl, (C.sub.1-C.sub.4)haloalkoxy, formyl,
(C.sub.1-C.sub.4)alkylcarbonyl and
(C.sub.1-C.sub.4)alkoxycarbonyl,
[0186] or (C.sub.3-C.sub.9)cycloalkyl, phenyl, phenoxy, phenylthio,
phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio or
heterocyclylamino,
[0187] where each of the last-mentioned 9 radicals is unsubstituted
or substituted, preferably unsubstituted or substituted by one or
more radicals selected from the group consisting of halogen,
hydroxyl, amino, nitro, formyl, carboxyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkyl, (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)haloalkoxy,
(C.sub.1-C.sub.4)alkylthio, (C.sub.1-C.sub.4)haloalkylthio,
mono(C.sub.1-C.sub.4)alkylamino, di(C.sub.1-C.sub.4)alkylamino,
(C.sub.3-C.sub.6)cycloalkyl, [(C.sub.1-C.sub.4)alkyl]carbonyl,
[(C.sub.1-C.sub.4)alkoxy]carbonyl, aminocarbonyl,
mono(C.sub.1-C.sub.4)alkylaminocarbonyl and
di(C.sub.1-C.sub.4)alkylaminocarbonyl,
[0188] or two adjacent radicals X together are a fused cycle having
4 to 6 ring atoms which is carbocyclic or contains hetero ring
atoms selected from the group consisting of O, S and N and which is
unsubstituted or substituted by one or more radicals selected from
the group consisting of halogen, (C.sub.1-C.sub.4)alkyl and
oxo.
[0189] In this context, n is preferably 0, 1, 2 or 3, in particular
0, 1 or 2.
[0190] (X).sub.n is also preferably n substituents X, where X in
each case independently of one another are halogen, hydroxyl,
amino, nitro, formyl, carboxyl, cyano, thiocyanato,
(C.sub.1-C.sub.4)alkyl, cyano-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy, (C.sub.1-C.sub.4)alkylamino,
di[(C.sub.1-C.sub.4)alkyl]amino, halo(C.sub.1-C.sub.4)alkyl,
_hydroxyl(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl,
halo(C.sub.1-C.sub.4)alko- xy-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylthio, halo(C.sub.1-C.sub.4)alkylthio,
(C.sub.2-C.sub.6)alkenyl, halo(C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkynyl, halo(C.sub.2-C.sub.6)alkynyl,
(C.sub.1-C.sub.4)alkylamino-(C.sub.1-C.sub.- 4)alkyl,
di[(C.sub.1-C.sub.4)alkyl]amino-(C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.6)cycloalkylamino-(C.sub.1-C.sub.4)alkyl,
(C.sub.3-C.sub.9)cycloalkyl, heterocyclyl-(C.sub.1-C.sub.4)alkyl
having 3 to 9 ring members, where the cyclic groups in the
last-mentioned 3 radicals are unsubstituted or substituted by one
or more radicals, preferably up to three radicals, selected from
the group consisting of (C.sub.1-C.sub.4)alkyl, halogen and cyano,
or phenyl, phenoxy, phenylcarbonyl,
phenylcarbonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkoxy-carbonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkylaminocarbonyl-(C.sub.1-C.sub.4)alkyl,
(C.sub.1-C.sub.4)alkyl-carbonyl, (C.sub.1-C.sub.4)alkoxycarbonyl,
aminocarbonyl, (C.sub.1-C.sub.4)alkylaminocarbonyl,
phenoxy-(C.sub.1-C.sub.4)alkyl, phenyl-(C.sub.1-C.sub.4)alkyl,
heterocyclyl, heterocyclylamino, heterocyclyloxy, heterocyclylthio
or one of the last-mentioned 16 radicals which is substituted in
the acyclic moiety or, preferably in the cyclic moiety by one or
more radicals selected from the group consisting of halogen, nitro,
cyano, C.sub.1-C.sub.4)alkyl, C.sub.1-C.sub.4)alkoxy,
(C.sub.1-C.sub.4)alkylthio- , (C.sub.1-C.sub.4)haloalkyl,
(C.sub.1-C.sub.4)haloalkoxy, formyl,
(C.sub.1-C.sub.4)alkylcarbonyl, C.sub.1-C.sub.4)alkoxycarbonyl,
(C.sub.1-C.sub.4)alkoxy, where heterocyclyl in the radicals
contains in each case 3 to 9 ring atoms and 1 to 3 hetero ring
atoms selected from the group consisting of N, O and S, or two
adjacent radicals X together are a fused cycle having 4 to 6 ring
atoms which is carbocyclic or contains hetero ring atoms selected
from the group consisting of O, S and N and which is unsubstituted
or substituted by one or more radicals selected from the group
consisting of halogen, (C.sub.1-C.sub.4)alkyl and oxo.
[0191] (X).sub.n is especially preferably n substituents X and
where X in each case independently of one another are halogen, OH,
NO.sub.2, CN, SCN (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.4)alkylca- rbonyl or
(C.sub.1-C.sub.4)alkyloxycarbonyl, where the last-mentioned four
radicals are unsubstituted or substituted by halogen or
(C.sub.1-C.sub.4)alkoxy, and
[0192] very especially preferably n substituents X and where X in
each case independently of one another are halogen, hydroxyl,
(C.sub.1-C.sub.4)alkyl or (C.sub.1-C.sub.4)alkoxy.
[0193] Heterocyclyl in the radicals mentioned hereinabove or
further below are, independently of one another preferably a
heterocyclic radical having 3 to 7 ring atoms selected from the
group consisting of N, O and S, preferably a heteroaromatic radical
selected from the group consisting of pyridyl, pyrimidinyl,
pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl,
thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl,
imidazolyl and triazolyl or a partially or fully hydrogenated
heterocyclic radical selected from the group consisting of
oxiranyl, oxetanyl, oxolanyl (=tetrahydrofuryl), oxanyl,
pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, oxazolinyl,
isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl.
[0194] Especially preferably, heterocyclyl is a heterocyclic
radical having 3 to 6 ring atoms and one (1) hetero atom selected
from the group consisting of N, O and S, in particular a
heteroaromatic radical having 5 or 6 ring atoms or a saturated or
partially unsaturated heterocyclic (not heteroaromatic) radical
having 3 to 6 ring atoms.
[0195] Moreover, heterocyclyl is preferably a heterocyclic radical
having 5 or 6 ring atoms and 2 or 3 hetero atoms selected from the
group consisting of N, O and S, in particular pyrimidinyl,
pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl,
oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, triazolyl or
piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,
isoxazolidinyl or morpholinyl.
[0196] The composite group --A.sup.2-R.sup.2 is preferably
cyclopropyl (hereinbelow also "c-Pr"), CH.sub.2-c-Pr,
-(CH.sub.2).sub.2-c-Pr, cyclobutyl (hereinbelow also "c-Bu"),
CH.sub.2-c-Bu; (CH.sub.2).sub.2-c-Bu, oxiranyl, oxiranylmethyl or
2-(oxiranyl)-eth-1-yl.
[0197] Subject matter of the present invention are also processes
for the preparation of compounds of the formula (I) and their salts
13
[0198] where A.sup.1, A.sup.2, L.sup.0, R.sup.1, R.sup.2, R.sup.3,
R.sup.4, X and n are as defined hereinabove, wherein
[0199] a) in the event that R.sup.3 in formula (I) is a group of
the formula -L.sup.1-N.dbd.C(U.sup.1)(U.sup.3), where L.sup.1,
U.sup.1 and U.sup.3 are as defined further above under R.sup.3, a
compound of the formula (II) 14
[0200] where A.sup.1, A.sup.2, L.sup.0, L.sup.1, R.sup.1, R.sup.2,
R.sup.4, X and n are as defined in formula (I) is reacted with a
compound of the formula (III) 15
[0201] where U.sup.1 and U.sup.3 are as defined in formula (I) and
R.sup.18 and R.sup.19 independently of one another are
unsubstituted or substituted alkyl having up to 12 carbon atoms,
preferably (C.sub.1-C.sub.4)alkyl, or jointly linked are an
alkylene group having 2 to 4 carbon atoms, or
[0202] b) in the event that R.sup.3 in formula (I) is a group of
the formula L.sup.1-NG.sup.1-C(U.sup.2)=N-U.sup.4 where L.sup.1,
G.sup.1, U.sup.2 and U.sup.4 are as defined further above under
R.sup.3, a compound of the formula (IV) 16
[0203] where A.sup.1, A.sup.2, L.sup.0, L.sup.1, R.sup.1, R.sup.2,
R.sup.4, G.sup.1, X and n are as defined in formula (I) is reacted
with a compound of the formula (V) 17
[0204] where U.sup.2 and U.sup.4 are as defined in formula (I) and
R.sup.18 is as defined in formula (III), or
[0205] c) in the event that R.sup.3 in formula (I) is a group of
the formula -L.sup.1-N.dbd.C(U.sup.1)(U.sup.3) where
U.sup.3=NG.sup.18NG.sup.- 19G.sup.20, NG.sup.21OG.sup.22 or
NG.sup.23SG.sup.24 and L.sup.1, U.sup.1, G.sup.18, G.sup.19,
G.sup.20, G.sup.21, G.sup.22, G.sup.23, G.sup.24 are as defined
further above under R.sup.3, a compound of the formula (VI) 18
[0206] where A.sup.1, A.sup.2, L.sup.0, L.sup.1, R.sup.1, R.sup.2,
R.sup.4, U.sup.1, X and n are as defined in formula (I) and R.sup.6
and R.sup.7 are as defined further above, is reacted with a
compound of the formula (VII) or its acid adducts
H--U.sup.3 (VII)
[0207] where U.sup.3 is as defined in formula (I), or
[0208] d) in the event that R.sup.3 in formula (I) is a group of
the formula -L.sup.1-N.dbd.C(U.sup.1)(U.sup.3) where
U.sup.1=R.sup.14 and U.sup.3=R.sup.15 and L.sup.1, R.sup.14 and
R.sup.15 are as defined further above, a compound of the formula
(II) is reacted in accordance with variant a) with an aldehyde or
ketone of the formula (VIII)
U.sup.1--CO--U.sup.3 (VII)
[0209] where U.sup.1 and U.sup.3 are as defined in formula (I).
[0210] The substituted aminotriazines of the formula (II) used in
the process according to the invention, variant a) for the
preparation of compounds of the formula (I) are known and/or can be
prepared by processes known per se (cf. WO-A-9965882).
[0211] The starting materials of the formula (Ill) are known (cf.
Chem. Ber. 89, 2060 (1956), Liebigs Anm. Chem. 641, 1 (1961), Chem.
Ber. 96, 1350 (1963)) or can be prepared analogously to the known
processes.
[0212] If appropriate, variant a) of the process according to the
invention for the preparation of compounds of the formula (I) is
carried out using a diluent. Suitable diluents for this purpose
are, mainly, 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, ethylene glycol dimethyl ether or ethylene glycol
diethyl ether; ketones such as acetone, butanone or methyl isobutyl
ketone; nitrites such as acetonitrile, propionitrile or
butyronitrile; amides such as N,N-dimethylformamide,
N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or
hexamethylphosphoric triamide; esters such as methyl acetate or
ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such
as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl
ether, ethylene glycol monoethyl ether, diethylene glycol
monomethyl ether or diethylene glycol monoethyl ether. When
carrying out the process according to the invention, the reaction
temperatures can be varied within a substantial range. In general,
the process is carried out at temperatures between 0.degree. C. and
150.degree. C., preferably between 10.degree. C. and 120.degree.
C.
[0213] As a rule, the process according to the invention is carried
out under atmospheric pressure. However, it is also possible to
carry out the process according to the invention under elevated or
reduced pressure, in general between 0.1 bar and 10 bar.
[0214] To carry out the process according to the invention, the
starting materials are employed in, for example, equimolar amounts.
However, it is also possible to use one of the components in a more
or less large excess, for example when the component of which
substoichiometric amounts are used is to complete its reaction
quickly in order to reduce side reactions. The reaction is carried
out for example in a suitable diluent in the presence of a reaction
auxiliary, the reaction mixture generally being mixed, for example
stirred, for several hours at the temperature required. Work-up can
be carried out by customary methods (cf. also the Preparation
Examples).
[0215] The substituted aminotriazines of the formula (IV) used in
variant b) of the process according to the invention for the
preparation of compounds of the formula (I) are known and/or can be
prepared by processes known per se (cf. WO-A-9965882).
[0216] The compounds of the formula (V) are known, for example,
from J. Org. Chem. 30, pp. 2531-2533 (1965).
[0217] If appropriate, variant b) of the process according to the
invention for the preparation of compounds of the formula (I) is
carried out using a diluent. Suitable diluents for this purpose
are, mainly, 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, 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-methylformanilide, N-methylpyrrolidone or
hexamethylphosphoric triamide; esters such as methyl acetate or
ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such
as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl
ether, ethylene glycol monoethyl ether, diethylene glycol
monomethyl ether or diethylene glycol monoethyl ether.
[0218] When carrying out the process according to the invention,
the reaction temperatures can be varied within a substantial range.
In general, the process is carried out at temperatures between
0.degree. C. and 150.degree. C., preferably between 10.degree. C.
and 120.degree. C.
[0219] Variant b) of the process according to the invention is
carried out in a simple manner, for example under atmospheric
pressure. However, it is also possible to carry out the process
according to the invention under elevated or reduced pressure,
preferably between 0.1 bar and 10 bar.
[0220] To carry out variant b) of the process, the starting
materials can be employed in equimolar amounts. However, it is also
possible to use one of the components in a more or less large
excess. The reaction is preferably carried out in a suitable
diluent in the presence of a reaction auxiliary. As a rule, the
reaction proceeds to completion in the course of several hours with
stirring at the temperature required. Work-up can be carried out by
customary methods (cf. the Preparation Examples).
[0221] To prepare the compounds (I) following variant c), compounds
of the formula (VI) are employed. Compounds of the formula (VI) can
be prepared from amino compounds of the formula (II) following
variant a), for example by reaction with compounds of the formula
(Ill) where U.sup.1, R.sup.18, R.sup.19 are as defined in formula
(Ill) and U.sup.3=NR.sup.6R.sup.7, where R.sup.6 and R.sup.7 are as
defined in formula (I) (=Compounds (IIIa)). The compounds of the
formula (VII) are known or can be prepared by known methods. If
appropriate, variant c) of the process according to the invention
is carried out using a diluent. Suitable diluents for this purpose
are, mainly, 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, ethylene glycol dimethyl ether or ethylene glycol
diethyl ether; ketones such as acetone, butanone or methyl isobutyl
ketone; nitrites such as acetonitrile, propionitrile or
butyronitrile; amides such as N,N-dimethylformamide,
N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or
hexamethylphosphoric triamide; esters such as methyl acetate or
ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such
as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl
ether, ethylene glycol monoethyl ether, diethylene glycol
monomethyl ether or diethylene glycol monoethyl ether.
[0222] The other reaction conditions, such as ranges for reaction
temperatures, pressure conditions, proportions and the like are
similar to those in variants a) and b).
[0223] If appropriate, variant d) of the process according to the
invention is carried out using a diluent. Suitable diluents for
this purpose are, mainly, 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, 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-methylformanilide,
N-methylpyrrolidone or hexamethylphosphoric triamide; esters such
as methyl acetate or ethyl acetate; sulfoxides such as dimethyl
sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol,
ethylene glycol monomethyl ether, ethylene glycol monoethyl ether,
diethylene glycol monomethyl ether or diethylene glycol monoethyl
ether.
[0224] The compounds of the formula (VII) which are employed in
variant d) of the process are known or can be prepared by known
methods.
[0225] The other reaction conditions, such as ranges for reaction
temperatures, pressure conditions, proportions and the like are
similar to those in variants a) and b) and c).
[0226] The water which is liberated during the reaction (reaction
water) can be removed for example by azeotropic distillation,
water-binding salts or molecular sieves.
[0227] The respective starting compounds of the formulae (II) to
(VIII) are known or can be prepared by the abovementioned methods
or analogously to known processes.
[0228] The following acids are suitable for preparing the acid
addition salts of the compounds of the formula (I): hydrohalic
acids such as hydrochloric acid or hydrobromic acid, furthermore
phosphoric acid, nitric acid, sulfuric acid, mono- or bifunctional
carboxylic acids and hydroxycarboxylic acids such as acetic acid,
maleic acid, succinic acid, fumaric acid, tartaric acid, citric
acid, salicylic acid, sorbic acid or lactic acid, and also sulfonic
acids such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic
acid. The acid addition compounds of the formula (I) can be
obtained simply by the customary salt formation methods, for
example by dissolving a compound of the formula (I) in a suitable
organic solvent such as, for example, methanol, acetone, methylene
chloride or benzine, and adding the acid at temperatures of from 0
to 100.degree. C., and they can be isolated in a known fashion, for
example by filtration, and, if appropriate, purified by washing
with an inert organic solvent.
[0229] The base addition salts of the compounds of the formula (I)
are preferably prepared in inert polar solvents such as, for
example, water, methanol or acetone at temperature from 0 to
100.degree. C. Examples of suitable bases for preparing the salts
according to the invention are alkali metal carbonates, such as
potassium carbonate, alkali metal and alkaline earth metal
hydroxides, for example NaOH or KOH, alkali metal and alkaline
earth metal hydrides, for example NaH, alkali metal and alkaline
earth metal alkoxides, for example sodium methoxide, potassium
tert-butoxide, or ammonia or ethanolamine. Quaternary ammonium
salts can be obtained, for example, by salt exchange or
condensation with quaternary ammonium salts of the formula
[NRR'R"R'"].sup.+X.sup.-where R, R', R"and R'" independently of one
another are (C.sub.1-C.sub.4)alkyl, phenyl or benzyl and X.sup.-is
an anion, for example Cl.sup.-or OH.sup.-.
[0230] The "inert solvents" which the above process variants refer
to are to be understood as meaning in each case solvents which are
inert under the reaction conditions in question, but which need not
be inert under any desired reaction conditions.
[0231] A collection of compounds (I) which can be synthesized by
the abovementioned processes can additionally be prepared in
parallelized fashion, which can be effected manually, partly
automated or fully automated. In this context, it is possible to
automate the procedure of the reaction, work-up or purification of
the products or intermediates. In total, this is to be understood
as meaning a procedure which is described, for example, by S. H.
DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular
Diversity: Automated Synthesis", Volume 1, published by Escom,
1997, pages 69 to 77.
[0232] For carrying out the reaction and work-up in parallelized
fashion, a series of commercially available apparatuses can be used
as they are available from, for example, Stem Corporation,
Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England or H+P
Labortechnik GmbH, Bruckmannring 28, 85764 Oberschlei.beta.heim,
Germany. To carry out the parallelized purification of compounds
(I) or of intermediates obtained during the preparation, there are
available, inter alia, chromatographic equipment, for example from
ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA. The
equipment mentioned makes possible a modular procedure, where the
individual steps are automated, but manual operation has to be
carried out between the steps. This can be circumvented by
employing partly or fully integrated automation systems, in which
the automation modules in question are operated by, for example,
robots. Such automation systems can be obtained from, for example,
Zymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.
[0233] In addition to the above-described methods, compounds (I)
can be prepared in full or partly by solid-phase supported methods.
To this end, individual intermediates or all intermediates of the
synthesis or of a synthesis adapted to the procedure in question
are bound to a synthesis resin. Solid-phase supported synthetic
methods are described extensively in the specialist literature, for
example: Barry A. Bunin in "The Combinatorial Index", published by
Academic Press, 1998.
[0234] The use of solid-phase supported synthesis methods permits a
series of protocols known from the literature which, in turn, can
be carried out manually or in an automated fashion. For example,
the "teabag method" (Houghten, U.S. Pat. No. 4,631,211; Houghten et
al., Proc. Natl. Acad. Sci., 1985, 82, 5131 - 5135) can be partly
automated with products of IRORI, 11149 North Torrey Pines Road, La
Jolla, Calif. 92037, USA. Solid-phase supported parallel synthesis
can be automated successfully for example using equipment by
Argonaut Technologies, Inc., 887 Industrial Road, San Carlos,
Calif. 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454
Witten, Germany.
[0235] The preparation in accordance with the processes described
herein yields compounds (I) in the form of substance collections or
substance libraries. Subject matter of the present invention are
therefore also libraries of the compounds (I) which contain at
least two compounds (I), and of their precursors.
[0236] The compounds of the formula (I) according to the invention
and their salts, hereinbelow together termed compounds of the
formula (I) (according to the invention) have an excellent
herbicidal activity against a broad spectrum of economically
important mono- and dicotyledonous harmful plants. The active
substances also act efficiently on perennial weeds which produce
shoots from rhizomes, root stocks or other perennial organs and are
difficult to control. In this context, it is unimportant whether
the substances are applied before sowing, preemergence or
postemergence.
[0237] Specifically, some representatives of the mono- and
dicotyledonous weed flora which can be controlled by the compounds
according to the invention may be mentioned by way of example,
without a restriction to certain species being intended to take
place as a result of the mention.
[0238] Amongst the monocotyledonous weed species, those on which
the active substances act efficiently are, for example, Agrostis,
Alopecurus, Apera, Avena, Brachicaria, Bromus, Dactyloctenium,
Digitaria, Echinochloa, Eleocharis, Eleusine, Festuca,
Fimbristylis, Ischaemum, Lolium, Monochoria, Panicum, Paspalum,
Phalaris, Phleum, Poa, Sagittaria, Scirpus, Setaria, Sphenoclea and
Cyperus species from the annual group and, amongst the perennial
species, Agropyron, Cynodon, Imperata and Sorghum and also
perennial Cyperus species. In the case of dicotyledonous weed
species, the spectrum of action extends to species such as, for
example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus,
Sinapis, lpomoea, Matricaria, Abutilon and Sida amongst the annuals
and Convolvulus, Cirsium, Rumex and Artemisia in the case of the
perennial weeds. Herbicidal action is also achieved in the case of
dicotyledonous harmful plants such as
[0239] Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium,
Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium,
Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa,
Rotala, Seneceio, Sesbania, Solanum, Sonchus, Taraxacum, Trifolium,
Urtica and Xanthium.
[0240] Harmful plants occurring under the specific cultivation
conditions of rice, such as, for example, Sagittaria, Alisma,
Eleocharis, Scirpus and Cyperus, are also outstandingly well
controlled by the active substances according to the invention.
[0241] If the compounds according to the invention are applied to
the soil surface before germination, then the weed seedlings are
either prevented completely from emerging or the weeds grow until
they have reached the cotyledon stage, but then their growth stops
and they finally die completely after three to four weeks have
elapsed. When the active substances are applied postemergence to
the green parts of the plants, growth stops equally drastically a
very short time after treatment and the weed plants remain at the
stage of growth at the time of application, or they die completely
after a certain time, so that in this manner competition by the
weeds, which is harmful to the crop plants, is eliminated at a very
early stage and in a sustained manner.
[0242] Although the compounds according to the invention have an
excellent herbicidal activity against mono- and dicotyledonous
weeds, crop plants of economically important crops such as, for
example, wheat, barley, rye, triticale, rice, maize, sugar beet,
cotton and soybeans, are damaged only to an insignificant extent or
not at all. For these reasons, the present compounds are very
highly suitable for the selective control of undesired vegetation
in stands of agriculturally useful plants or in stands of
ornamental plants.
[0243] In addition, the substances according to the invention have
outstanding growth-regulatory properties in crop plants. They
engage in the plants' metabolism in a regulatory fashion and can
thus be employed for influencing plant constituents in a targeted
fashion and for facilitating harvesting, such as, for example, by
triggering desiccation and stunted growth. Moreover, they are also
suitable for generally controlling and inhibiting undesired
vegetative growth without simultaneously killing the plants.
Inhibiting vegetative growth plays an important role in many
monocotyledonous and dicotyledonous crops since lodging can be
reduced, or prevented completely, hereby.
[0244] On account of their herbicidal and plant growth-regulatory
properties, the active substances can also be employed for the
control of harmful plants in crops of known genetically modified
plants or genetically modified plants yet to be developed. As a
rule, the transgenic plants are distinguished by particularly
advantageous properties, for example by resistances to certain
pesticides, especially certain herbicides, resistances to plant
diseases or pathogens of plant diseases such as certain insects or
microorganisms such as fungi, bacteria or viruses. Other particular
properties relate, for example, to the harvested material with
respect to quantity, quality, storability, composition and specific
constituents. Thus, transgenic plants having an increased starch
content or where the quality of the starch is altered or those
having a different fatty acid composition of the harvested material
are known.
[0245] The compounds of the formula (I) according to the invention
or their salts are preferably used in economically important
transgenic crops of useful and ornamental plants, e.g. of cereals
such as wheat, barley, rye, oats, sorghum and millet, rice, cassava
and corn or alternatively crops of sugar beet, cotton, soybeans,
oilseed rape, potatoes, tomatoes, peas and other types of
vegetables.
[0246] The compounds of the formula (I) can preferably be employed
as herbicides in useful plant crops which are resistant, or have
been made resistant, by recombinant methods, to the phytotoxic
effects of the herbicides.
[0247] Traditional ways of generating novel plants which have
modified characteristics in comparison with existing plants
consist, for example, in traditional breeding methods and the
generation of mutants. Alternatively, novel plants with modified
characteristics can be generated using recombinant procedures (see,
for example, EP-A-0221044, EP-A-0131624). For example, a number of
cases have been described of
[0248] recombinant modifications of crop plants for the purpose of
modifying the starch synthesized in the plants (e.g. WO 92/11376,
WO 92/14827, WO 91/19806),
[0249] transgenic crop plants which are resistant to certain
herbicides of the glufosinate type (cf., for example, EP-A-0242236,
EP-A-242246) or of the glyphosate type (WO 92/00377) or of the
sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),
[0250] transgenic crop plants, for example cotton, with the
capability of producing Bacillus thuringiensis toxins (Bt toxins)
which make the plants resistant to certain pests (EP-A-0142924,
EP-A-0193259),
[0251] transgenic crop plants having a modified fatty acid
composition (WO 91/13972).
[0252] Numerous molecular biology techniques using which novel
transgenic plants having modified properties can be produced are
known in principle; see, for example, Sambrook et al., 1989,
Molecular Cloning, A Laboratory Manual, 2nd Ed., Cold Spring Harbor
Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker "Gene und
Klone" [Genes and Clones], VCH Weinheim, 2nd Edition, 1996 or
Christou, "Trends in Plant Science" 1 (1996) 423-431).
[0253] For recombinant manipulations of this type, nucleic acid
molecules can be introduced into plasmids which allow mutagenesis
or a sequence modification by means of recombination of DNA
sequences. With the aid of the abovementioned standard procedures,
it is possible, for example, to perform base exchanges, to remove
subsequences or to add natural or synthetic sequences. For the
connection of the DNA fragments to one another, adaptors or linkers
can be attached to the fragments.
[0254] For example, plant cells having a reduced activity of a gene
product can be produced by the expression of at least one
corresponding antisense RNA, a sense RNA to achieve a cosuppression
effect or the expression of at least one appropriately constructed
ribozyme which specifically cleaves transcripts of the
abovementioned gene product.
[0255] For this, it is possible to use, on the one hand, DNA
molecules which comprise the entire coding sequence of a gene
product including flanking sequences which may be present, and also
DNA molecules which only comprise parts of the coding sequence,
where these parts must be long enough in order to bring about an
antisense effect in the cells. The use of DNA sequences which have
a high degree of homology to the coding sequences of a gene
product, but are not completely identical, is also possible.
[0256] When nucleic acid molecules are expressed in plants, the
synthesized protein can be localized in any desired compartment of
the plant cell. However, in order to achieve localization in a
certain compartment, it is possible, for example, to link the
coding region with DNA sequences which guarantee localization in a
certain compartment. Sequences of this type are known to the person
skilled in the art (see, for example, Braun et al., EMBO J. 11
(1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85
(1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
[0257] The transgenic plant cells can be regenerated to give intact
plants according to known techniques. In principle, the transgenic
plants can be plants of any desired plant species, i.e. both
monocotyledonous and dicotyledonous plants.
[0258] Transgenic plants are thus obtainable which have modified
properties as a result of overexpression, suppression or inhibition
of homologous (=natural) genes or gene sequences or expression of
heterologous (=foreign) genes or gene sequences.
[0259] The compounds (I) according to the invention can preferably
be employed in transgenic crops which are resistant to herbicides
from the group consisting of the sulfonylureas,
glufosinate-ammonium or glyphosate-isopropylammonium and analogous
active substances.
[0260] When the active substances according to the invention are
used in transgenic crops, in addition to the effects against
harmful plants to be observed in other crops, effects often occur
which are specific for application in the particular transgenic
crop, for example a modified or specifically widened spectrum of
weeds which can be controlled, altered application rates which can
be employed for application, preferably good combining ability with
the herbicides to which the transgenic crop is resistant, and an
effect on growth and yield of the transgenic crop plants.
[0261] The invention therefore also relates to the use of the
compounds (I) according to the invention as herbicides for
controlling harmful plants in transgenic crop plants.
[0262] The use according to the invention for controlling harmful
plants or for regulating the growth of plants also includes the
case where the active substance of the formula (I) or its salt is
formed from a prodrug only after application on the plant, in the
plant or in the soil.
[0263] The compounds according to the invention can be used in the
customary preparations in the form of wettable powders,
emulsifiable concentrates, sprayable solutions, dusting agents or
granules. The invention therefore also relates to herbicidal and
plant growth-regulating compositions which contain compounds of the
formula (I).
[0264] The compounds of the formula (I) can be formulated in
various ways, depending on what biological and/or chemicophysical
parameters are prespecified. Examples of suitable formulation
possibilities are: wettable powders (WP), water-soluble powders
(SP), water-soluble concentrates, emulsifiable concentrates (EC),
emulsions (EW), such as oil-in-water and water-in-oil emulsions,
sprayable solutions, suspension concentrates (SC), dispersions on
an oil or water basis, oil-miscible solutions, capsule suspensions
(CS), dusting agents (DP), dressing agents, granules for
broadcasting and soil application, granules (GR) in the form of
microgranules, spray granules, coated granules and adsorption
granules, water-dispersible granules (WG), water-soluble granules
(SG), ULV formulations, microcapsules and waxes.
[0265] These individual formulation types are known in principle
and are described, for example, in: Winnacker-Kuchler, "Chemische
Technologie" [Chemical Technology], Volume 7, C. Hauser Vedag
Munich, 4th Edition 1986, Wade van Valkenburg, "Pesticide
Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray
Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.
[0266] The necessary or applicable formulation auxiliaries such as
inert materials, surfactants, solvents and other additives are also
in many cases known and are described, for example, in: Watkins,
"Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed.,
Darland Books, Caldwell N.J., H. v. Olphen, "Introduction to Clay
Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden,
"Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's
"Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood
N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents",
Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, "Grenzflchenaktive
thylenoxidaddukte" [Surface-Active Ethylene Oxide Adducts], Wiss.
Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, "Chemische
Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag
Munich, 4th Edition 1986.
[0267] On the basis of these formulations, combinations with other
pesticidally active substances such as, for example, insecticides,
acaricides, herbicides, fungicides, and also with safeners,
fertilizers and/or growth regulators can also be prepared, e.g. in
the form of a finished formulation or as a tank mix.
[0268] Wettable powders are preparations which are uniformly
dispersible in water and which, besides the active compound, also
contain surfactants of ionic and/or nonionic type (wetting agents,
dispersants), e.g. polyoxyethylated alkylphenols, polyoxethylated
fatty alcohols, polyoxethylated fatty amines, fatty alcohol
polyglycol ether sulfates, alkanesulfonates,
alkylbenzenesulfonates, sodium lignosulfonates, sodium
2,2'-dinaphthylmethane-6,6'-disulfonate, sodium
dibutylnaphthalene-sulfon- ate or alternatively sodium
oleoylmethyltaurate in addition to a diluent or inert substance.
For preparation of the wettable powders, the herbicidal active
substances are finely ground, for example, in customary equipment
such as hammer mills, blowing mills and air-jet mills and
simultaneously or subsequently mixed with the formulation
auxiliaries.
[0269] Emulsifiable concentrates are prepared by dissolving the
active substance in an organic solvent, e.g. butanol,
cyclohexanone, dimethylformamide, xylene or alternatively
relatively high-boiling aromatics or hydrocarbons or mixtures of
the organic solvents with addition of one or more surfactants of
ionic and/or nonionic type (emulsifiers). Examples of emulsifiers
which can be used are: alkylarylsulfonic acid calcium salts such as
Ca dodecylbenzenesulfonate or nonionic emulsifiers such as fatty
acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol
polyglycol ethers, propylene oxide-ethylene oxide condensation
products, alkyl polyethers, sorbitan esters such as, for example,
sorbitan fatty acid esters or polyoxyethylene sorbitan esters such
as, for example, polyoxyethylene sorbitan fatty acid esters.
[0270] Dusting agents are obtained by grinding the active substance
with finely divided solid substances, e.g. talc, natural clays,
such as kaolin, bentonite and pyrophyllite, or diatomaceous
earth.
[0271] Suspension concentrates can be water- or oil-based. They can
be prepared, for example, by wet grinding by means of commercially
available bead mills and, if appropriate, addition of surfactants,
such as have already been mentioned, for example, above in the case
of the other formulation types.
[0272] Emulsions, e.g. oil-in-water emulsions (EW), can be
prepared, for example, by means of stirrers, colloid mills and/or
static mixers using aqueous organic solvents and, if appropriate,
surfactants, such as have already been mentioned, for example,
above in the case of the other formulation types.
[0273] Granules can either be prepared by spraying the active
substance onto adsorptive, granulated inert material or by applying
active substance concentrates to the surface of carriers such as
sand, kaolinites or of granulated inert material by means of
binders, e.g. polyvinyl alcohol, sodium polyacrylate or
alternatively mineral oils. Suitable active substances can also be
granulated in the manner customary for the preparation of
fertilizer granules--if desired as a mixture with fertilizers.
[0274] As a rule, water-dispersible granules are prepared by the
customary processes such as spray-drying, fluidized bed
granulation, disk granulation, mixing using high-speed mixers and
extrusion without solid inert material. For the preparation of
disk, fluidized bed, extruder and spray granules, see, for example,
processes in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd.,
London; J. E. Browning, "Agglomeration", Chemical and Engineering
1967, pages 147 ff; "Perry's Chemical Engineer's Handbook", 5th
Ed., McGraw-Hill, New York 1973, pp. 8-57.
[0275] For further details on the formulation of plant protection
materials see, for example, G. C. Klingman, "Weed Control as a
Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96
and J. D. Freyer, S. A. Evans, "Weed Control Handbook", 5th Ed.,
Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
[0276] As a rule, the agrochemical preparations contain 0.1 to 99%
by weight, in particular 0.1 to 95% by weight, of active substance
of the formula (I).
[0277] In wettable powders, the active substance concentration is,
for example, approximately 10 to 90% by weight, the remainder to
100% by weight consists of customary formulation constituents. In
the case of emulsifiable concentrates, the active substance
concentration can be approximately 1 to 90, preferably 5 to 80, %
by weight. Formulations in the form of dusts contain 1 to 30% by
weight of active substance, preferably usually 5 to 20% by weight
of active substance, sprayable solutions contain approximately 0.05
to 80, preferably 2 to 50, % by weight of active substance. In the
case of water-dispersible granules, the active substance content
depends partly on whether the active compound is liquid or solid
and which granulation auxiliaries, fillers etc. are used. In the
case of water-dispersible granules, the content of active substance
is, for example, between 1 and 95% by weight, preferably between 10
and 80% by weight.
[0278] In addition, the active substance formulations mentioned
optionally contain the binders, wetting agents, dispersants,
emulsifiers, penetrants, preservatives, antifreeze agents,
solvents, fillers, carriers, colorants, antifoams, evaporation
inhibitors and the pH and viscosity regulators which are customary
in each case.
[0279] The compounds of the formula (I) or their salts can be
employed as such or in the form of their preparations
(formulations) as combinations with other pesticidally active
substances, such as, for example, insecticides, acaricides,
nematicides, herbicides, fungicides, safeners, fertilizers and/or
growth regulators, for example as a premix or as tank mixes.
[0280] Components which may be employed for the active substances
according to the invention in mixed formulations or in tank mix
are, for example, known active compounds which are based on an
inhibition of, for example, acetolactate synthase, acetyl-coenzyme
A carboxylase, PS I, PS II, HPPDO, phytoene desaturase,
protoporphyrinogen oxidase, glutamine synthetase, cellulose
biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase. Such
compounds, and also other compounds which can be employed, whose
mechanism of action is to a degree unknown or different, are
described, for example, in Weed Research 26, 441-445 (1986), or
"The Pesticide Manual", 11th Edition 1997 (hereinbelow also
abbreviated to "PM") and 12th Edition 2000, The British Crop
Protection Council and the Royal Soc. of Chemistry (editors) and
literature cited therein. Herbicides which are known from the
literature and which can be mentioned, which can be combined with
the compounds of the formula (I), are, for example, the following
active substances. (Note: the compounds are either designated by
the common name according to the International Organization for
Standardization (ISO) or using the chemical name, if appropriate
together with a customary code number): acetochlor;
acifluorfen(-sodium); aclonifen; AKH 7088, i.e.
[[[1-[5-[2-chloro-4-(trif- luoromethyl)
phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetic acid
and its methyl ester; alachlor; alloxydim(-sodium); ametryn;
amicarbazone, amidochlor, amidosulfuron; amitrol; AMS, i.e.
ammonium sulfamate; anilofos; asulam; atrazin; azafenidin,
azimsulfurone (DPX-A8947); aziprotryn; barban; BAS 516 H, i.e.
5-fluoro-2-phenyl-4H-3,1- -benzoxazin-4-one; beflubutamid,
benazolin(-ethyl); benfluralin; benfuresate; bensulfuron(-methyl);
bensulide; bentazone; benzobicyclon, benzofenap; benzofluor,
benzoylprop(-ethyl); benzthiazuron; bialaphos; bifenox;
bispyribac(-sodium), bromacil; bromobutide; bromofenoxim;
bromoxynil; bromuron; buminafos; busoxinone; butachlor;
butafenacil, butamifos; butenachlor; buthidazole; butralin;
butroxydim, butylate; cafenstrole (CH-900); carbetamide;
carfentrazone(-ethyl) (ICI-A0051); caloxydim, CDM, i.e.
2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chloroallyl
diethyldithiocarbamate; chlomethoxyfen; chloramben;
chlorazifop-butyl, chlormesulon (ICI-A0051); chlorbromuron;
chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon;
chlorimuron(-ethyl); chlomitrofen; chlorotoluron; chloroxuron;
chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid;
chlortoluron, cinidon(-methyl and -ethyl), cinmethylin;
cinosulfuron; clefoxydim, clethodim; clodinafop and its ester
derivatives (for example clodinafop-propargyl); clomazone;
clomeprop; cloproxydim; clopyralid; clopyrasulfuron(-methyl),
cloransulam(-methyl), cumyluron (JC 940); cyanazine; cycloate;
cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its
ester derivatives (for example the butyl ester, DEH-1 12);
cyperquat; cyprazine; cyprazole; daimuron; 2,4-D, 2,4-DB; 2,4-DB,
dalapon; desmedipham; desmetryn; di-allate; dicamba; dichlobenil;
dichlorprop; diclofop and its esters such as diclofop-methyl;
diclosulam, diethatyl(-ethyl); difenoxuron; difenzoquat;
diflufenican; diflufenzopyr, dimefuron; dimepiperate, dimethachlor;
dimethametryn; dimethenamid (SAN-582H); dimethazone, dimexyflam,
dimethipin; dimetrasulfuron, dinitramine; dinoseb; dinoterb;
diphenamid; dipropetryn; diquat; dithiopyr; diuron; DNOC;
eglinazine-ethyl; EL 77, i.e.
5-cyano-1-(1,1-dimethylethyl)-N-methyl-IH-pyrazole4-carboxamide;
endothal; epoprodan, EPTC; esprocarb; ethalfluralin;
ethametsulfuron-methyl; ethidimuron; ethiozin; ethofumesate;
ethoxyfen and its esters (for example the ethyl ester, HN-252);
ethoxysulfuron, etobenzanid (HW 52); F5231, i.e.
N-[2-chloro-4-fluoro-5-[4-(3-fluoropropy- l)4,
5-dihydro-5-oxo-1H-tetrazol-1-ylphenyl]ethanesulfon amide;
fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters,
for example fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim;
fentrazamide, fenuron; flamprop(-methyl or -isopropyl or
-isopropyl-L); flazasulfuron; floazulate, florasulam, fluazifop and
fluazifop-P and their esters, for example fluazifop-butyl and
fluazifop-P-butyl; flucarbazone(-sodium), fluchloralin;
flumetsulam; flumeturon; flumiclorac(-pentyl), flumioxazin (S482);
flumipropyn; fluometuron, fluorochloridone, fluorodifen;
fluoroglycofen(-ethyl); flupoxam (KNW-739); flupropacil (UBIC4243);
flupyrsulfuron(-methyl or -sodium), flurenol(-butyl), fluridone;
flurochloridone; fluroxypyr(-meptyl); flurprimidol, flurtamone;
fluthiacet(-methyl), fluthiamide, fomesafen; foramsulfuron,
fosamine; furyloxyfen; glufosinate(-ammonium);
glyphosate(-isopropylammonium); halosafen; halosulfuron(-methyl)
and its esters (for example the methyl ester, NC-319); haloxyfop
and its esters; haloxyfop-P (=R-haloxyfop) and its esters;
hexazinone; imazamethabenz(-methyl); imazapyr; imazaquin and salts
such as the ammonium salt; imazamethapyr, imazamox, imazapic,
imazethamethapyr; imazethapyr; imazosulfuron; indanofan, ioxynil;
isocarbamid; isopropalin; isoproturon; isouron; isoxaben;
isoxachlortole, isoxaflutole, isoxapyrifop; karbutilate; lactofen;
lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidid;
mesosulfuron, mesotrione, metamitron; metazachlor;
methabenzthiazuron; metham; methazole; methoxyphenone;
methyidymron; metabenzuron, methobenzuron; metobromuron;
(alpha-)metolachlor; metosulam (XRD 511); metoxuron; metnbuzin;
metsulfuron-methyl; MH; molinate; monalide; monocarbamide
dihydrogensulfate; monolinuron; monuron; MT 128, i.e.
6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine;
MT 5950, i.e.
N-[3-chloro4-(1-methylethyl)-phenyl]-2-methylpentanamide;
naproanilide; napropamide; naptalam; NC 310, i.e.
4-(2,4-dichlorobenzoyl)- -1-methyl-5-benzyloxypyrazole; neburon;
nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen;
norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630);
oxadiazon; oxasulfuron, oxaziclomefone, oxyfluorfen; paraquat;
pebulate; pelargonic acid, pendimethalin; pentoxazone, perfluidone;
phenisopham; phenmedipham; picloram; picolinafen, piperophos;
piributicarb; pirifenop-butyl; pretilachlor;
primisulfuron(-methyl); procarbazone-(sodium), procyazine;
prodiamine; profluralin; proglinazine(-ethyl); prometon; prometryn;
propachlor; propanil; propaquizafop and its esters; propazine;
propham; propisochlor; propyzamide; prosulfalin; prosulfocarb;
prosulfuron (CGA-152005); prynachlor; pyraflufen(-ethyl),
pyrazolinate; pyrazon; pyrazosulfuron(-ethyl); pyrazoxyfen;
pyribenzoxim, pyributicarb, pyridafol, pyridate;
pyrimidobac(-methyl), pyrithiobac(-sodium) (KIH-2031); pyroxofop
and its esters (for example the propargyl ester); quinclorac;
quinmerac; quinoclamine, quinofop and its ester derivatives,
quizalofop and quizalofop-P and their ester derivatives, for
example quizalofop-ethyl; quizalofop-P-tefuryl and -ethyl;
renrduron; rimsulfuron (DPX-E 9636); S 275, i.e.
2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4- ,
5,6,7-tetrahydro-2H-indazole; secbumeton; sethoxydim; siduron;
simazine; simetryn; SN 106279, i.e.
2-[17-[2-chloro-4-(trifluoromethyl)phenoxyl-2-n- aphthalenyl
]oxy]propanoic acid and its methyl ester; sulcotrione, sulfentrazon
(FMC-97285, F-6285); sulfazuron; sulfometuron(-methyl); sulfosate
(ICI-A0224); sulfosulfuron, TCA; tebutam (GCP-5544); tebuthiuron;
tepraloxydim, terbacil; terbucarb; terbuchlor; terbumeton;
terbuthylazine; terbutryn; TFH 450, i.e.
N,N-diethyl-3-[(2-ethyl-6-methyl- phenyl)-sulfonyl]-1
H-1,2,4-triazole-1 -carboxamide; thenylchlor (NSK-850);
thiafluamide, thiazafluron; thiazopyr (Mon-13200); thidiazimin
(SN-24085); thifensulfuron(-methyl); thiobencarb; tiocarbazil;
tralkoxydim; tri-allate; tnasulfuron; triaziflam, triazofenamide;
tribenuron(-methyl); triclopyr; tridiphane; trietazine;
trifluralin; triflusulfuron and its esters (for example the methyl
ester, DPX-66037); tnmeturon; tritosulfuron, tsitodef; vemolate; WL
110547, i.e. 5-phenoxy-1 -[3-(trifluoromethyl)phenyl]-1
H-tetrazole; BAY MKH 6561, UBH-509; D-489; LS 82-556; KPP-300;
NC-324; NC-330; KH-218; DPX-N8189; SC-0774; DOWCO-535; DK-8910;
V-53482; PP-600; MBH-001; KIH-9201; ET-751; KIH-6127 and
KIH-2023.
[0281] Controlling harmful plants selectively is of particular
interest in crops of useful plants and ornamentals. Even though the
compounds (I) already exhibit very good to sufficient selectivity
in many crops, it is possible, in principle, that symptoms of
phytotoxicity occur on the cultivated plants in some crops and
especially also in the case of mixtures with other herbicides which
are less selective. In this respect, combinations of compounds (I)
according to the invention which are of particular interest are
those which contain the compounds (I) or their combinations with
other herbicides or pesticides and safeners. The safeners, which
are employed in such an amount that they act as antidote, reduce
the phytotoxic side effects of the herbicides/pesticides employed,
for example in economically important crops such as cereals (wheat,
barley, rye, maize, rice, sorghum and millet), sugar beet, sugar
cane, oilseed rape, cotton and soybeans, preferably cereals. The
following groups of compounds are examples of suitable safeners for
the compounds (I) and their combinations with further
pesticides:
[0282] a) compounds of the dichlorophenylpyrazoline-3-carboxylic
acid type, preferably compounds such as ethyl
1-(2,4-dichlorophenyl)-5-
(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1)
("Mefenpyr-diethyl", PM, pp. 781-782) and related compounds as they
are described in WO 91/07874;
[0283] b) dichlorophenylpyrazolecarboxylic acid derivatives,
preferably compounds such as ethyl
1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxy- late (S1-2),
ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylat- e
(S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1
-dimethylethyl)pyrazole-3-ca- rboxylate (S1-4), ethyl
1-(2,4-dichlorophenyl5-phenylpyrazole-3-carboxylat- e (S1-5) and
related compounds as they are described in EP-A-333 131 and
EP-A-269 806;
[0284] c) compounds of the triazolecarboxylic acids type,
preferably compounds such as fenchlorazol (and its ethyl ester),
i.e. ethyl
1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylat-
e (S1-6), and related compounds (see EP-A-174 562 and EP-A-346
620);
[0285] d) compounds of the 5-benzyl- or
5-phenyl-2-isoxazoline-3-carboxyli- c acid type or the
5,5-diphenyl-2-isoxazoline-3-carboxylic acid, preferably compounds
such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3- -carboxylate
(S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (SI-8) and
related compounds as they are described in WO 91/08202, or ethyl
5,5-diphenyl-2-isoxazolinecarboxylate (S1-9) ("isoxadifen-ethyl")
or n-propyl 5,5-diphenyl-2-isoxazolinecarboxylate (SI-10) or ethyl
5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-11), as
they are described in German Patent Application
(WO-A-95/07897);
[0286] e) compounds of the 8-quinolinoxyacetic acid type (S2),
preferably 1-methylhex-1-yl (5-chloro-8-quinolinoxy)acetate (common
name "cloquintocet-mexyl") (S2-1) (see PM, pp. 263-264)
1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (S2-2),
4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3),
1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl
(5-chloro-8-quinolinoxy)ace- tate (S2-5), methyl
(5-chloro-8-quinolinoxy)acetate (S2-6), allyl
(5-chloro-8-quinolinoxy)acetate (S2-7),
2-(2-propylideneiminooxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate
(52-8), 2-oxoprop-1-yl (5-chloro -8-quinolinoxy )acetate (52-9),
and related compounds as are described in EP-A-86 750, EP-A-94 349
and EP-A-191 736 or EP-A-0 492 366;
[0287] f) compounds of the (5-chloro-8-quinolinoxy)malonic acid
type, preferably compounds such as diethyl
(5-chloro-8-quinolinoxy)malonate, diallyl
(5-chloro-8-quinolinoxy)malonate, methylethyl
(5-chloro-8-quinolinoxy)malonate and related compounds as are
described in EP-A-0 582 198;
[0288] g) active substances of the phenoxyacetic or
phenoxypropionic acid derivatives type or of the aromatic
carboxylic acids type, such as, for example,
2,4-dichlorophenoxyacetic acids (and its esters) (2,4-D),
4-chloro-2-methylphenoxypropionic esters (mecoprop), MCPA or
3,6-dichloro-2-methoxybenzoic acid (and its esters) (dicamba);
[0289] h) active substances of the pyrimidines type which are
employed in rice as soil-acting safeners, such as, for example,
"fenclorim" (PM, pp. 511-512) (=4,6-dichloro-2-phenylpyrimidine),
which is also known as safener for pretilachlor in seeded rice;
[0290] i) active substances of the dichloroacetamides type, which
are frequently employed as pre-emergence safeners (soil-acting
safeners), such as, for example, "dichlormid" (PM, pp. 363-364)
(=N,N-diallyl-2,2-dichloroacetamide), "R-29148"
(=3-dichloroacetyl-2,2,5-- trimethyl-1,3-oxazolidine, by Stauffer),
"benoxacor" (PM, pp.102-103)
(=4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1, 4-benzoxazine),
"PPG-1292" (=N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide
by PPG Industries), "DK-24"
(=N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacet- amide by
Sagro-Chem), "AD-67" or "MON 4660" (=3-dichloroacetyl-1
oxa-3-azaspiro[4,5]decane by Nitrokemia and Monsanto,
respectively), "diclonon" or "BAS145138" or "LAB145138"
(=3-dichloroacetyl-2, 5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane
by BASF) and "furilazol" or "MON 13900" (see PM, 637-638)
(=(RS)-3-dichloroacetyl-5-(2-furyl)2, 2-dimethyloxazolidine);
[0291] j) active substances of the dichloroacetone derivatives
type, such as, for example, "MG 191" (CAS Reg. No. 96420-72-3)
(=2-dichloromethyl-2-methyl-1, 3-dioxolane by Nitrokemia), which is
known as safener for maize;
[0292] k) active substances of the oxyimino compounds type, which
are known as seed treatment products, such as, for example,
"oxabetrinil" (PM, pp. 902-903)
(=(Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)-acetonitril- e), which
is known as seed-treatment safener for sorghum and millet against
metolachlor damage, "fluxofenim" (PM, pp. 613-614)
(=1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone
O-(1,3-dioxolan-2-ylmethy- l)oxime, which is known as seed-dressing
safener for sorghum and millet against metolachlor damage, and
"cyometrinil" or "-CGA43089" (PM, p. 1304) (=(Z)-cyanomethoxy-imino
(phenyl)acetonitrile), which is known as seed-treatment safener for
sorghum and millet against metolachlor damage;
[0293] l) active substances of the thiazolecarboxylic ester type,
which are known as seed treatment products, such as, for example,
"flurazol" (PM, pp. 590-591) (=benzyl 2-chloro4-trifluoromethyl-1
,3-thiazole-5-carboxylate), which is known as seed-treatment
safener for sorghum and millet against alachlor and metolachlor
damage;
[0294] m) active substances of the naphthalenedicarboxylic acid
derivatives type, which are known as seed treatment products, such
as, for example, "naphthalic anhydride" (PM, p. 1342)
(=1,8-naphthalenedicarb- oxylic anhydride), which is known as
seed-treatment safener for maize against thiocarbamate herbicide
damage;
[0295] n) active substances of the chromanacetic acid derivatives
type, such as, for example, "CL 304415" (CAS Reg. No. 31541-57-8)
(=2-(4-carboxychroman4-yl)acetic acid by American Cyanamid), which
is known as safener for maize against damage by imidazolinones;
[0296] o) active substances which, in addition to a herbicidal
action against harmful plants, also exhibit a safener action in
connection with crop plants such as rice, such as, for example,
"dimepiperate" or "MY-93" (PM, pp. 404405) (=S-1
-methyl-1-phenylethyl piperidine-1-carbothioate), which is known as
safener for rice against damage by the herbicide molinate,
"daimuron" or "SK 23" (PM, p. 330) (=1-(1-methyl-1-phenylethyl)-
-3-p-tolylurea), which is known as safener for rice against damage
by the herbicide imazosulfuron, "cumyluron" ="JC-940"
(=3-(2-chlorophenylmethyl)- -1-(1-methyl-1-phenyl-ethyl) urea, see
JP-A-60087254), which is known as safener for rice against damage
by several herbicides, "methoxyphenone" or "NK 049"
(=3,3'-dimethyl4-methoxybenzophenone), which is known as safener
for rice against damage by several herbicides, "CSB"
(=1-bromo4-(chloromethylsulfonyl)benzene) (CAS Reg. No. 54091-064,
by Kumiai), which is known as safener in rice against damage by
several herbicides;
[0297] p) N-acylsulfonamides of the formula (S3) and their salts
19
[0298] as are described in WO-A-97/45016;
[0299] q) acylsulfamoylbenzamides of the formula (S4), if
appropriate also in salt form, 20
[0300] as are described in International Application No.
PCT/EP98/06097; and
[0301] r) compounds of the formula (S5), 21
[0302] as are described in WO-A 98/13 361, including the
stereoisomers and the salts conventionally used in agriculture.
[0303] Amongst the safeners mentioned, those which are of
particular interest are (S1-1) and (S1-9) and (S2-1), in particular
(S1-1) and (S1-9).
[0304] Some of the safeners are already known as herbicides and
therefore simultaneously also display a protective action in
connection with the crop plants in addition to the herbicidal
action in connection with harmful plants.
[0305] The weight ratio of herbicide (mixture) to safener generally
depends on the application rate of herbicide and the efficacy of
the safener in question; it can vary within wide limits, for
example in the range of from 200:1 to 1:200, preferably from 100:1
to 1:100, in particular 20:1 to 1:20. The safeners can be
formulated with further herbicides/pesticides, analogously to the
compounds (I) or their mixtures, and provided and used as readymix
or tank mix together with the herbicides.
[0306] For use, the herbicide or herbicide safener formulations,
which are present in a customary commercial form, are, if
appropriate, diluted in the customary fashion, for example using
water in the case of wettable powders, emulsifiable concentrates,
dispersions and water-dispersible granules. Preparations in the
form of dusts, soil granules, granules for spreading, and sprayable
solutions, are usually not diluted further with other inert
materials prior to use.
[0307] The application rate required of the compounds of the
formula (I) varies with, inter alia, the external conditions such
as temperature, humidity and the type of the herbicide used. It can
vary within wide limits, for example between 0.001 and 10.0 kg/ha
or more of active substance, but it is preferably between 0.005 and
5 kg/ha, in particular 0.01 and 3 kg/ha.
[0308] In the examples which follow, quantities (also percentages)
are weight-based, unless specifically indicated.
A. CHEMICAL EXAMPLES
Example A1
2-Dimethylaminomethyleneamino4-(1-fluoro-1-methylethyl)-6-(1-cyclopropyl
4-phenyl-1-butylamino)-1,3,5-triazine (see Table 8, Example
8-2)
[0309] A solution of 1.71 g (5 mmol) of
2-amino4-(1-fluoro-1-methylethyl)--
6-(1-cyclopropyl-4-phenyl-1-butylamino)-1, 3,5-triazine and 2 ml of
N,N-dimethylformamide dimethyl acetal in 30 ml of toluene is
refluxed for 2 hours. All volatile constituents are subsequently
carefully distilled off. This gives 1.94 g (97.5% of theory) of
2-dimethylaminomethyleneamino- -4-(1 -fluoro-1 -methylethyl)-6-(l
-cyclopropyl4-phenyl-1-butylamino)-1, 3,5-triazine as colorless
oil.
Example A2
N-[4-(1-Fluorol
-methylethyl)-6-(1-cyclopropyl-4-phenyl-1-butylamino)-1,
3,5-triazin-2-yl]formamide oxime (see Table 8, Example 8-27)
[0310] 0.69 g (10 mmol) of hydroxylamine hydrochloride are added
with stirring at room temperature to a solution of 1.99 g (5 mmol)
of
2-dimethylaminomethyleneamino-4-(1-fluoro-1-methylethyl)-6-(1-cyclopropyl-
-4-phenyl-1-butylaminoyl,3, 5-triazine in 20 ml of methanol. The
reaction mixture is stirred for 2 hours at room temperature. All
volatile constituents are carefully distilled off. The crude
product is taken up in methylene chloride. The mixture is washed
with water, dried over Na.sub.2SO.sub.4 and evaporated in vacuo.
This gives 1.81 g (93.7% of theory) of N-[4-(1
-fluoro-1-methylethyl)-6-(1-cyclopropyl-4-phenyl-1-but- ylamino)-1,
3,5-triazin-1-yl]formamide oxime as pale yellow oil.
Example A3
2-(4-Chlorobenzylideneamino)4-(l -fluoro-1 -methylethyl)-6-(1
-cyclopropyl-4-phenyl-1-butylamino)-1, 3,5-triazine (see Table 8,
Example 8-37)
[0311] A mixture of 2.5 g (7.28 mmol) of
2-amino-4-(1-fluoro-1-methylethyl-
)-6-(1-cyclopropyl4-phenyl-1-butylamino)-1, 3,5-triazine, 1.08 g
(7.70 mmol) of p-chlorobenzaldehyde and 100 mg of p-toluenesulfonic
acid in 80 ml of toluene are boiled for 10 hours in a water
separator. When cold, all volatile constituents are distilled. The
crude product is purified by column chromatography (eluent:
toluene/ethyl acetate=85:15). This gives 3.0 g (89% of theory) of
2-(4-chloro-6-benzylideneamino)-4-(1-fluoro-1-me-
thylethyl)-6-(1-cyclopropyl-4-phenyl-1-butylamino-1, 3,5-triazine
as colorless oil.
[0312] The compounds described in Tables 1 to 12 hereinbelow are
obtained in accordance with, or analogously to, the above Examples
A1 to A3 or the methods which have been described in general
further above. In the tables, the abbreviations have the following
meanings:
[0313] Me=methyl
[0314] Et=ethyl
[0315] Pr=propyl
[0316] i-Pr=isopropyl
[0317] c-Pr=cyclopropyl
[0318] c-Bu=cyclobutyl
[0319] t-Bu=tertiary butyl
[0320] c-hexyl =cyclohexyl
[0321] Al =(CH.sub.2).sub.1 =-CH2-
[0322] Ph - phenyl
[0323] Bz =benzyl
[0324] A2=(CH.sub.2).sub.2 =-CH.sub.2CH.sub.2-
[0325] A3=(CH.sub.2).sub.3 -CH.sub.2CH.sub.2CH.sub.2-
[0326] A4 =(CH.sub.2).sub.4 =-CH.sub.2CH.sub.2CH.sub.2CH.sub.2-
[0327] Ac=COCH.sub.3 =acetyl
[0328] Ox= 22
[0329] =oxiranyl
[0330] Ph=phenyl
[0331] (X).sub.n="-" corresponds to n=0
[0332] Tables 1 to 11 which follow refer to formula (I) where
L.sup.0=a direct bond and R.sup.4=hydrogen atom: 23
1TABLE 1 Physical data and stereochemical No. R.sup.1
A.sup.2-R.sup.2 R.sup.3 A.sup.1 (X).sub.n information 1-1
CH.sub.2OCH.sub.3 c-Pr N.dbd.CH--NMe.sub.2 A.sup.1 4-Cl racemate
1-2 CH(CH.sub.3)(OCH.sub.3) c-Pr N.dbd.CH--NMe.sub.2 A.sup.1 4-Cl
racemate 1-3 CHMe.sub.2 c-Pr N.dbd.CH--NMe.sub.2 A.sup.1 4-F
racemate 1-4 CH.sub.2OEt c-Pr N.dbd.C(Et)NEt.sub.2 A.sup.1 4-Cl
racemate 1-5 CH.sub.2CF.sub.3 c-Pr N.dbd.C(Ph)(NMe.sub.2) A.sup.1
4-Cl racemate 1-6 Ph c-Bu N.dbd.C(4-MePh)(NMe.sub.2) A.sup.1 4-Br
racemate 1-7 CH.sub.2Ph c-Bu- N.dbd.C(CH.sub.2Ph)(NMe.sub.2)
A.sup.1 4-Cl racemate 1-8 CH(CH.sub.3)(CH.sub.2CF.sub.3) c-phenyl
N.dbd.C(OMe)(NMe.sub.2) A.sup.1 4-Br racemate 1-9 Me c-Pr
NH--CH.dbd.N--OH A.sup.1 4-Cl racemate 1-10 Et c-Pr
NH--CH.dbd.N--OH A.sup.1 2,4-Cl.sub.2 racemate 1-11 c-Pr c-Pr
NH--CH.dbd.N--NH.sub.2 A.sup.1 2,4-Cl.sub.2 racemate 1-12 c-Pr c-Pr
NH--CH.dbd.N--NMe.sub.2 A.sup.1 2,4,6-Cl.sub.3 racemate 1-13 c-Bu
CH.sub.2Ph NHN.dbd.CHN(Ph).sub.2 A.sup.1 4-Cl racemate 1-14 c-Bu
CH.sub.2Ph N.dbd.CHPh A.sup.1 -- racemate
[0333]
2TABLE 2 Physical data and stereochemical No. R.sup.1
A.sup.2-R.sup.2 R.sup.3 A.sup.1 (X).sub.n information 2-1
CHMe.sub.2 c-Pr N.dbd.CH--NMe.sub.2 A.sup.2 -- racemate, oil 2-2
CHFMe c-Pr N.dbd.CH--NMe.sub.2 A.sup.2 4-J racemate 2-3 CHFEt c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3-Br racemate 2-4 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 4-Na racemate 2-5 Me c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 -- racemate 2-6 Et c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 -- racemate 2-7 CHMe.sub.2 c-Pr
N.dbd.C(Me)(NMe.sub.2) A.sup.2 -- racemate 2-8 CFMe.sub.2 c-Pr
N.dbd.C(Me)(NMe.sub.2) A.sup.2 4-CF.sub.3 racemate 2-9 CHFMe c-Pr
N.dbd.C(Me)(NMe.sub.2) A.sup.2 4-CF.sub.3 racemate 2-10 CHFEt c-Pr
N.dbd.C(Me)(NMe.sub.2) A.sup.2 4-CF.sub.3 racemate 2-11 CFMe.sub.2
c-Pr N.dbd.CH--NEt.sub.2 A.sup.2 4-CF.sub.3 racemate 2-12 CHFEt
c-Pr N.dbd.CH--NEt.sub.2 A.sup.2 4-CF.sub.3 racemate 2-13
CHMe.sub.2 c-Pr N.dbd.CH--NEt.sub.2 A.sup.2 4-CF.sub.3 racemate
2-14 CFMe.sub.2 c-Pr N.dbd.C(Me)N(CH.sub.2CH.sub.2OH).sub.2 A.sup.2
4-CF.sub.3 racemate 2-15 CFMe.sub.2 c-Pr N.dbd.CH--NEt.sub.2
A.sup.2 -- racemate 2-16 CFMe.sub.2 c-Pr N.dbd.CH--NEt.sub.2
A.sup.2 3-Me racemate 2-17 CFMe.sub.2 c-Pr N.dbd.CH--NEt.sub.2
A.sup.2 3-Cl racemate 2-18 CFMe.sub.2 c-Pr N.dbd.CH--NEt.sub.2
A.sup.2 3,5-Me.sub.2 racemate 2-19 CFMe.sub.2 c-Pr
N.dbd.CH--NEt.sub.2 A.sup.2 3-F racemate 2-20 CHFMe c-Pr
N.dbd.CH--NEt.sub.2 A.sup.2 -- racemate 2-21 CHFMe c-Pr
N.dbd.CH--NEt.sub.2 A.sup.2 3-Me racemate 2-22 CHFMe c-Pr
N.dbd.CH--NEt.sub.2 A.sup.2 3-Cl racemate 2-23 CHFMe c-Pr
N.dbd.CH--NEt.sub.2 A.sup.2 3,5-Me.sub.2 racemate 2-24 CHFMe c-Pr
N.dbd.CH--NEt.sub.2 A.sup.2 3-F racemate 2-25 CHFEt c-Pr
N.dbd.CH--NEt.sub.2 A.sup.2 -- racemate 2-26 CHFEt c-Pr
N.dbd.CH--NEt.sub.2 A.sup.2 3-Me racemate 2-27 CHFEt c-Pr
N.dbd.CH--NEt.sub.2 A.sup.2 3-Cl racemate 2-28 CHFEt c-Pr
N.dbd.CH--NEt.sub.2 A.sup.2 3,5-Me.sub.2 racemate 2-29 CHFEt c-Pr
N.dbd.CH--NEt.sub.2 A.sup.2 3-F racemate 2-30 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 -- racemate 2-31 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3-Me racemate 2-32 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3-Cl racemate 2-33 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3,5-Me.sub.2 racemate 2-34 CFMe.sub.2
c-Pr N.dbd.CH--NMe.sub.2 A.sup.2 3-F racemate 2-35 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 -- racemate, oil 2-36 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3-Me racemate, oil 2-37 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3-Cl racemate 2-38 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3,5-Me.sub.2 racemate 2-39 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3-F racemate 2-40 CHFEt c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 -- racemate 2-41 CHFEt c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3-Me racemate 2-42 CHFEt c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3-Cl racemate 2-43 CHFEt c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3,5-Me.sub.2 racemate 2-44 CHFEt c-Pr
N.dbd.CH--NMe.sub.2 A.sup.2 3-F racemate 2-45 CFMe.sub.2 c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 -- racemate, oil 2-46 CFMe.sub.2 c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 3-Me racemate 2-47 CFMe.sub.2 c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 3-Cl racemate 2-48 CFMe.sub.2 c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 3,5-Me.sub.2 racemate 2-49 CFMe.sub.2
c-Pr N.dbd.C(Me)NMe.sub.2 A.sup.2 3-F racemate 2-50 CHFMe c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 -- racemate 2-51 CHFMe c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 3-Me racemate 2-52 CHFMe c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 3-Cl racemate 2-53 CHFMe c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 3,5-Me.sub.2 racemate 2-54 CHFMe c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 3-F racemate 2-55 CHFEt c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 -- racemate, oil 2-56 CHFEt c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 3-Me racemate, oil 2-57 CHFEt c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 3-Cl racemate 2-58 CHFEt c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 3,5-Me.sub.2 racemate 2-59 CHFEt c-Pr
N.dbd.C(Me)NMe.sub.2 A.sup.2 3-F racemate 2-60 CFMe.sub.2 c-Pr
N.dbd.CHNMe.sub.2 OA1 -- racemate 2-61 CHFEr c-Pr N.dbd.CHNMe.sub.2
OA1 -- racemate 2-62 CClMe.sub.2 c-Pr N.dbd.C(Me)(NMe.sub.2) OA1 --
racemate 2-63 CHCeMe c-Pr N.dbd.CHNEt.sub.2 OA1 -- racemate 2-64 Me
c-Pr N.dbd.C(Et)(NEt.sub.2) OA1 -- racemate 2-65 Et c-Pr
N.dbd.C(Pr)(NMe.sub.2) OA1 -- racemate 2-66 CHMe.sub.2 c-Pr
N.dbd.C(Ph)(NEt.sub.2) OA1 -- racemate 2-67 CFMe.sub.2 c-Pr
N.dbd.C(n-Bu)(NMe.sub.2) OA1 3,5- racemate (OMe).sub.2 2-68
CFMe.sub.2 c-Pr NH.dbd.N.dbd.CHNMe.sub.2 OA1 -- racemate 2-69
CFMe.sub.2 c-Pr N.dbd.C(Me)(NMe.sub.2) OA1 3,5-Cl.sub.2 racemate
2-70 CFMe.sub.2 c-Pr N.dbd.C(Me)C(NPh.sub.2) OA1 3,5-F.sub.2
racemate 2-71 CBrMe.sub.2 c-Pr N.dbd.C(Me)(NEt.sub.2) OA1
2,5-F.sub.2 racemate 2-72 CClMe.sub.2 c-Pr N.dbd.CHN(n-Pr).sub.2
OA1 -- racemate 2-73 CHFEt c-Pr NH--CH.dbd.N--OH A2 -- racemate
2-74 CHFEt.sub.2 c-Pr NH--CH.dbd.N--OH A2 3-Cl racemate 2-75
CHFEt.sub.2 c-Pr NH--CH.dbd.N--OH A2 3-F racemate 2-76 CHFEt.sub.2
c-Pr NH--CH.dbd.N--OH A2 4-F, 3-Me racemate 2-77 CHFEt.sub.2 c-Pr
NH--CH.dbd.N--OH A2 3,4-F.sub.2 racemate 2-78 CFMe.sub.2 c-Pr
N.dbd.CH--Ph A2 -- racemate 2-79 CFMe.sub.2 c-Pr
N.dbd.CH-4-Cl--C.sub.6H.sub.4 A2 -- racemate 2-80 CFMe.sub.2 c-Pr
N.dbd.CH-4-F--C.sub.6H.sub.4 A2 -- racemate 2-81 CFMe.sub.2 c-Pr
N.dbd.CH-3,4-F.sub.2--C.sub.6H.sub.3 A2 -- racemate 2-82 CHFMe c-Pr
N.dbd.C(Me)(C.sub.6H.sub.5) A2 -- racemate 2-83 CHFMe c-Pr
NH--N.dbd.CHNMe.sub.2 A2 3,5-Me.sub.2 racemate 2-84 CHFMe c-Pr
NH--N.dbd.CHCHNMe.sub.2 A2 3,4-Me.sub.2 racemate 2-85 CHFMe c-Pr
NH--N.dbd.CHNMe.sub.2 A2 3-OEt racemate 2-86 CHFMe c-Pr
NH--N.dbd.CHNMe.sub.2 A2 3-OCF.sub.3 racemate 2-87 CHFMe c-Pr
NH--N.dbd.CHNMe.sub.2 A2 3-OCHF.sub.2 racemate 2-88 CFMe.sub.2 c-Pr
24 A2 -- racemate 2-89 CFMe.sub.2 c-Pr 25 A2 -- racemate 2-90
CFMe.sub.2 c-Pr 26 A2 -- racemate
[0334]
3TABLE 3 Physical data and stereochemical No. R.sup.1
A.sup.2-R.sup.2 R.sup.3 A.sup.1 (X).sub.n information 3-1
CFMe.sub.2 c-Bu N.dbd.CH--NMe.sub.2 A2 -- racemate, oil 3-2
CFMe.sub.2 c-Bu N.dbd.CH--NMe.sub.2 A2 3-Cl racemate 3-3 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 A2 3-OEt racemate 3-4 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 A2 3,5-Me.sub.2 racemate 3-5 CHMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 A2 3-O-i-Pr racemate 3-6 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 A2 -- racemate 3-7 CHFEt c-Bu
N.dbd.CH--NMe.sub.2 A2 -- racemate 3-8 Me c-Bu N.dbd.CH--NMe.sub.2
A2 -- racemate 3-9 Et c-Bu N.dbd.CH--NMe.sub.2 A2 -- racemate 3-10
CF.sub.3 c-Bu N.dbd.CH--NMe.sub.2 A2 -- racemate 3-11 CClMe.sub.2
c-Bu N.dbd.NH--NMe.sub.2 A2 -- racemate 3-12 CH.sub.2--O--CH.sub.3
c-Bu N.dbd.CH--NM.sub.2 A2 -- racemate 3-13 CF.sub.3 c-Bu
N.dbd.C(Me)(NMe.sub.2) A2 -- racemate 3-14 CFMe.sub.2 c-Bu
N.dbd.C(Me)(NMe.sub.2) A2 -- racemate, oil 3-15 CHFMe c-Bu
N.dbd.C(Me)(NMe.sub.2) A2 -- racemate 3-16 CHFEt c-Bu
N.dbd.C(Me)(NMe.sub.2) A2 -- racemate 3-17 Me c-Bu
N.dbd.C(Me)(NMe.sub.2) A2 -- racemate 3-18 c-Pr c-Bu
N.dbd.C(Me)(NMe.sub.2) A2 -- racemate 3-19 CFMe.sub.2 c-Bu
N.dbd.C(Me)(NMe2) A2 3-F racemate 3-20 CFMe.sub.2 c-Bu
N.dbd.C(Me)(NMe2) A2 3-CF.sub.3 racemate 3-21 CHFMe c-Bu
N.dbd.C(Me)(NMe.sub.2) A2 3-Cl racemate 3-22 CFMe.sub.2 c-Bu
N.dbd.C(Me)(NMe.sub.2) A2 3,4-Me.sub.2 racemate 3-23 CClMe.sub.2
c-Bu N.dbd.C(Me)(NMe.sub.2) A2 3-Cl, 5-Me racemate 3-24 c-Pr c-Bu
N.dbd.C(Me)(NMe.sub.2) A2 3,5-Me.sub.2 racemate 3-25 c-Pr c-Bu
N.dbd.C(Et)(NMe.sub.2) A2 -- racemate, oil 3-26 CFMe.sub.2 c-Bu
N.dbd.CHNEt.sub.2 A2 -- racemate 3-27 CHMe.sub.2 c-Bu
N.dbd.CHNEt.sub.2 A2 -- racemate 3-28 CF.sub.3 c-Bu
N.dbd.CHNEt.sub.2 A2 -- racemate 3-29 CH.sub.2F c-Bu
N.dbd.CHNEt.sub.2 A2 -- racemate 3-30 CFMe.sub.2 c-Bu
N.dbd.CHN(CH.sub.2CH.sub.2OH).sub.2 A2 -- racemate 3-31 CCH.sub.2Me
c-Bu N.dbd.C(Ph)(NEt.sub.2) A2 -- racemate 3-32 CCH.sub.2Cl c-Bu
N.dbd.C(Ph)(NEt.sub.2) A2 -- racemate 3-33 CCl.sub.3 c-Bu
N.dbd.C(Ph)(NEt.sub.2) A2 -- racemate 3-34 CHCl.sub.2 c-Bu
N.dbd.C(Ph)(N--Pr.sub.2) A2 -- racemate 3-35 CH.sub.2Cl c-Bu
N.dbd.C(3-Cl--Ph)(NMe.sub.2) A2 3,4-Cl.sub.2 racemate 3-36
CFMe.sub.2 c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3-Me racemate 3-37
CFMe.sub.2 c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3,4-F.sub.2 racemate, oil
3-38 CFMe.sub.2 c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3-OMe racemate, oil
3-39 CFMe.sub.2 c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3,4-(OMe).sub.2
racemate 3-40 CFMe.sub.2 c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3-F
racemate, oil 3-41 CFMe.sub.2 c-Bu N.dbd.C(Me)--NMe.sub.2 A2 4-F
racemate, oil 3-42 CHFMe c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3-Me
racemate, 3-43 CHFMe c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3,4-F.sub.2
racemate, oil 3-44 CHFMe c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3-OMe
racemate, oil 3-45 CHFMe c-Bu N.dbd.C(Me)--NMe.sub.2 A2
3,4-(OMe).sub.2 racemate 3-46 CHFMe c-Bu N.dbd.C(Me)--NMe.sub.2 A2
3-F racemate, oil 3-47 CHFMe c-Bu N.dbd.C(Me)--NMe.sub.2 A2 4-F
racemate, oil 3-48 CHFEt c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3-Me
racemate 3-49 CHFEt c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3,4-F.sub.2
racemate 3-50 CHFEt c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3-OMe racemate
3-51 CHFEt c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3,4-(OMe).sub.2 racemate
3-52 CHFEt c-Bu N.dbd.C(Me)--NMe.sub.2 A2 3-F racemate 3-53 CHFEt
c-Bu N.dbd.C(Me)--NMe.sub.2 A2 4-F racemate 3-54 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 A2 3-Me racemate 3-55 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 A2 3,4-F.sub.2 racemate, oil 3-56 CFMe.sub.2
c-Bu N.dbd.CH--NMe.sub.2 A2 3-OMe racemate, oil 3-57 CFMe.sub.2
c-Bu N.dbd.CH--NMe.sub.2 A2 3,4-(OMe).sub.2 racemate 3-58
CFMe.sub.2 c-Bu N.dbd.CH--NMe.sub.2 A2 3-F racemate, oil 3-59
CFMe.sub.2 c-Bu N.dbd.CH--NMe.sub.2 A2 4-F racemate, oil 3-60 CHFMe
c-Bu N.dbd.CH--NMe.sub.2 A2 3-Me racemate 3-61 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 A2 3,4-F.sub.2 racemate 3-62 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 A2 3-OMe racemate 3-63 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 A2 3,4-(OMe).sub.2 racemate 3-64 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 A2 3-F racemate 3-65 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 A2 4-F racemate 3-66 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 A2 3-Me racemate 3-67 CHFEt c-Bu
N.dbd.CH--NMe.sub.2 A2 3,4-F.sub.2 racemate, oil 3-68 CHFEt c-Bu
N.dbd.CH--NMe.sub.2 A2 3-OMe racemate, oil 3-69 CHFEt c-Bu
N.dbd.CH--NMe.sub.2 A2 3,4-(OMe).sub.2 racemate 3-70 CHFEt c-Bu
N.dbd.CH--NMe.sub.2 A2 3-F racemate, oil 3-71 CHFEt c-Bu
N.dbd.CH--NMe.sub.2 A2 4-F racemate, oil 3-72 CFMe.sub.2 c-Bu
N.dbd.CH--NEt.sub.2 A2 3-Me racemate 3-73 CFMe.sub.2 c-Bu
N.dbd.CH--NEt.sub.2 A2 3,4-F.sub.2 racemate 3-74 CFMe.sub.2 c-Bu
N.dbd.CH--NEt.sub.2 A2 3-OMe racemate, oil 3-75 CFMe.sub.2 c-Bu
N.dbd.CH--NEt.sub.2 A2 3,4-(OMe).sub.2 racemate 3-76 CFMe.sub.2
c-Bu N.dbd.CH--NEt.sub.2 A2 3-F racemate 3-77 CFMe.sub.2 c-Bu
N.dbd.CH--NEt.sub.2 A2 4-F racemate 3-78 CHFMe c-Bu
N.dbd.CH--NEt.sub.2 A2 3-Me racemate 3-79 CHFMe c-Bu
N.dbd.CH--NEt.sub.2 A2 3,4-F.sub.2 racemate 3-80 CHFMe c-Bu
N.dbd.CH--NEt.sub.2 A2 3-OMe racemate 3-81 CHFMe c-Bu
N.dbd.CH--NEt.sub.2 A2 3,4-(OMe).sub.2 racemate 3-82 CHFMe c-Bu
N.dbd.CH--NEt.sub.2 A2 3-F racemate 3-83 CHFMe c-Bu
N.dbd.CH--NEt.sub.2 A2 4-F racemate 3-84 CHFEt c-Bu
N.dbd.CH--NEt.sub.2 A2 3-Me racemate 3-85 CHFEt c-Bu
N.dbd.CH--NEt.sub.2 A2 3,4-F.sub.2 racemate, oil 3-86 CHFEt c-Bu
N.dbd.CH--NEt.sub.2 A2 3-OMe racemate, oil 3-87 CHFEt c-Bu
N.dbd.CH--NEt.sub.2 A2 3,4-(OMe).sub.2 racemate 3-88 CHFEt c-Bu
N.dbd.CH--NEt.sub.2 A2 3-F racemate 3-89 CHFEt c-Bu
N.dbd.CH--NEt.sub.2 A2 4-F racemate 3-90 CHFEt c-Bu
NH--CH.dbd.N--OH OA1 -- racemate 3-91 CHFMe c-Bu --NH--CH.dbd.N--OH
OA1 -- racemate 3-92 CHMe c-Bu --NH--CH.dbd.N--NH.sub.2 OA1 --
racemate 3-93 CHFEt c-Bu --NH--CH.dbd.N--NMe.sub.2 OA1 -- racemate
3-94 CFMe.sub.2 c-Bu N.dbd.CHPh OA1 -- racemate 3-95 CFMe.sub.2
c-Bu N.dbd.CH-3-Cl--C.sub.6H.sub.3 OA1 -- racemate 3-96 CF.sub.3
c-Bu N.dbd.CHPh OA1 3,5-Me.sub.2 racemate 3-97 CF.sub.3 c-Bu
N.dbd.CHPh OA1 3-F, 4-Me racemate 3-98 CF.sub.3 c-Bu N.dbd.CHPh OA1
3,5-Cl.sub.2 racemate 3-99 CF.sub.3 c-Bu N.dbd.CHPh OA1 3-Cl
racemate 3-100 CF.sub.3 c-Bu N.dbd.CHPh OA1 3,4-F.sub.2 racemate
3-101 CHF.sub.2 c-Bu N.dbd.CHPh OA1 2-Cl racemate 3-102 CH.sub.2F
c-Bu N.dbd.CH-2,3-Cl.sub.2--C.sub.6H.sub.3 OA1 2,5-Cl.sub.2
raccemate 3-103 CFMe.sub.2 c-Bu N.dbd.CH-3,5-Cl.sub.2C.sub.6H.sub-
.3 OA1 2,6-Cl.sub.2 racemate 3-104 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 A2 -- R enantiomer 3-105 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 A2 -- S enantiomer 3-106 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 OA1 -- R enantiomer 3-107 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 OA1 -- S enantiomer 3-108 CHMe.sub.2 c-Bu
NH--CH.dbd.N--OH A2 3-F racemate 3-109 CHBrMe c-Bu NH--CH.dbd.N--OH
A2 3-CF.sub.3 racemate 3-110 CHFMe c-Bu NHN.dbd.CHNMe.sub.2 A2 --
racemate 3-111 CFMe.sub.2 c-Bu NHN.dbd.CHNEt.sub.2 A2 -- racemate
3-112 CFMe.sub.2 c-Bu NH--NH--CH.dbd.NMe A2 -- racemate 3-113
CFMe.sub.2 c-Bu NH--CH.dbd.N--OH A2 -- racemate 3-114 CFMe.sub.2
c-Bu NH--CH.dbd.N--OH A2 4-Br racemate 3-115 CFMe.sub.2 c-Bu
NH--CH.dbd.N--OH A2 4-NO.sub.2 racemate 3-116 CFMe.sub.2 c-Bu
N.dbd.CHPh A2 3-NO.sub.2 racemate 3-117 CFMe.sub.2 c-Bu
N.dbd.CH-4-Cl--C.sub.6H.sub.4 A2 2-NO.sub.2 racemate 3-118
CFMe.sub.2 c-Bu N.dbd.CH-3-CH.sub.3--C.sub.6H.sub.4 A2 3-Cl
racemate 3-119 CFMe.sub.2 c-Bu N.dbd.CH-3-CF.sub.3--C.sub.6H.sub.4
A2 2,6-Cl.sub.2 racemate 3-120 CHFMe.sub.2 c-Bu 27 A2 -- racemate
3-121 CFMe.sub.2 c-Bu 28 A2 -- racemate 3-122 CFMe.sub.2 c-Bu 29 A2
-- racemate 3-123 CFMe.sub.2 c-Bu 30 A2 -- racemate 3-124
CFMe.sub.2 c-Bu 31 A2 -- racemate, oil 3-125 CFMe.sub.2 c-Bu 32 A2
-- racemate 3-126 H c-Bu N.dbd.CH--NEt.sub.2 A2 -- racemate 3-127
CFMe.sub.2 c-Bu NHN.dbd.CHNMe.sub.2 A2 -- racemate
[0335]
4TABLE 4 Physical data and stereochemical No. R.sup.1
A.sup.2-R.sup.2 R.sup.3 A.sup.1 (X).sub.n information 4-1
CFMe.sub.2 c-pentyl N.dbd.CHNMe.sub.2 A2 -- racemate 4-2 CFMe.sub.2
c-pentyl N.dbd.CHNMe.sub.2 A2 3,4-F.sub.2 racemate 4-3 CClMe.sub.2
c-pentyl N.dbd.CHNMe.sub.2 A2 -- racemate 4-4 CHCl.sub.2 c-pentyl
N.dbd.CHNMe.sub.2 A2 -- racemate 4-5 i-Pr c-hexyl N.dbd.CHNMe.sub.2
A2 -- racemate 4-6 i-Bu c-hexyl N.dbd.C(Me)NMe.sub.2 A2 -- racemate
4-7 CFMe.sub.2 c-pentyl 33 A2 -- racemate
[0336]
5TABLE 5 Physical data and stereochemical No. R.sup.1
A.sup.2-R.sup.2 R.sup.3 A.sup.1 (X).sub.n information 5-1
CFMe.sub.2 CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-Me racemate, oil
5-2 CFMe.sub.2 CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-OMe racemate
5-3 CFMe.sub.2 CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-Cl racemate
5-4 CFMe.sub.2 CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 -- racemate 5-5
CHFMe CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-Me racemate 5-6 CHFMe
CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-OMe racemate 5-7 CHFMe
CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-Cl racemate 5-8 CHFMe
CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 -- racemate 5-9 CHFEt
CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-Me racemate 5-10 CHFEt
CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-OMe racemate 5-11 CHFEt
CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-Cl racemate 5-12 CHFEt
CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 -- racemate 5-13 CHMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-Me racemate 5-14 CHMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-OMe racemate 5-15 CHMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 3-Cl racemate 5-16 CHMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NEt.sub.2 A2 -- racemate 5-17 CFMe.sub.2
CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 3-Me racemate 5-18
CFMe.sub.2 CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 3-OMe racemate,
oil 5-19 CFMe.sub.2 CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 3-Cl
racemate 5-20 CFMe.sub.2 CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 --
racemate 5-21 CHFMe CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 3-Me
racemate 5-22 CHFMe CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 3-OMe
racemate 5-23 CHFMe CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 3-Cl
racemate 5-24 CHFMe CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 --
racemate 5-25 CHFEt CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 3-Me
racemate 5-26 CHFEt CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 3-OMe
racemate 5-27 CHFEt CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 3-Cl
racemate 5-28 CHFEt CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 --
racemate 5-29 CFMe.sub.2 CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2
3-Me racemate 5-30 CFMe.sub.2 CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2
A2 3-OMe racemate 5-31 CFMe.sub.2 CH.sub.2-c-Pr
N.dbd.C(Me)--NMe.sub.2 A2 3-Cl racemate 5-32 CFMe.sub.2
CH.sub.2-c-Pr N.dbd.C(Me)--NMe.sub.2 A2 -- racemate 5-33 CFMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 3-Me racemate 5-34 CFMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 3-OME racemate 5-35 CFMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 3-Cl racemate 5-36 CFMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 -- racemate, oil 5-37 CHFMe
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 3-Me racemate 5-38 CHFMe
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 3-OME racemate 5-39 CHFMe
CH.sub.2-Pr N.dbd.CH--NMe.sub.2 A2 3-Cl racemate 5-40 CHFMe
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 -- racemate, oil 5-41 CHFEt
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 3-Me racemate 5-42 CHFEt
CH.sub.2-Pr N.dbd.CH--NMe.sub.2 A2 3-OMe racemate 5-43 CHFEt
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 3-Cl racemate 5-44 CHFEt
CH.sub.2-c-Pr N.dbd.CH-NMe.sub.2 A2 -- racemate 5-45 CHMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 3-Me racemate 5-46 CHMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 3-OMe racemate 5-47 CHMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 3-Cl racemate 5-48 CHMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 A2 -- racemate 5-49 CFMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 OA1 -- racemate 5-50 CHMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 OA1 -- racemate 5-51 Ph
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 OA1 -- racemate 5-52 c-Bu
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 SA1 -- racemate 5-53 c-pentyl
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 SA1 -- racemate 5-54 c-Pr
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 SA1 -- racemate 5-55 CF.sub.3
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 SA1 -- racemate 5-56 CFMe.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 NMeA1 -- racemate 5-57 CHFMe
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 NMe-A1 -- racemate 5-58
CFMe.sub.2 CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 NEt-A1 -- racemate
5-59 CHFPr CH.sub.2-c-Pr N.dbd.CH-NMe.sub.2 NEt-A1 -- racemate 5-60
CH.sub.2CH.sub.2CF.sub.3 CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 NPh-A1
-- racemate 5-61 CF.sub.2CHF.sub.2 CH.sub.2-c-Pr
N.dbd.CH--NMe.sub.2 NPh-A1 -- racemate 5-62 CFCl.sub.2
CH.sub.2-c-Pr N.dbd.CH--NMe.sub.2 NBz-A1 2-NO.sub.2 racemate 5-63
CFMe.sub.2 CH.sub.2-c-Pr N.dbd.CHNMe--Ph A2 2-NO.sub.2 racemate
5-64 CFMe.sub.2 CH.sub.2-c-Pr N.dbd.CHNMePh A2 -- racemate 5-65
CFMe.sub.2 CH.sub.2-c-Pr N.dbd.C(Me)NMe.sub.2) A2 -- racemate 5-66
CFMe.sub.2 CH.sub.2-c-Pr N.dbd.C(NMe.sub.2)(NMeNMe.sub.2) A2 --
racemate 5-67 CFMe CH.sub.2-c-Pr N.dbd.C(NEt.sub.2)(NMeNMe.sub.2)
A2 -- racemate 5-68 CH.sub.2F CH.sub.2-c-Pr N.dbd.C(SMe)(NMe.sub.2)
A2 -- racemate 5-69 CH.sub.2F CH.sub.2-c-Pr N.dbd.C(SMe)(NMeOMe) A2
-- racemate 5-70 CH.sub.2F CH.sub.2-c-Pr N.dbd.C(SMe)(NMeNMe.sub.2-
) A2 -- racemate 5-71 CH.sub.2CH.sub.2CF.sub.3 CH.sub.2-c-Pr
N.dbd.C(Et)(NHNH.sub.2) A2 -- racemate 5-72
CH.sub.2CH.sub.2CF.sub.3 CH.sub.2-c-Pr NH--N.dbd.CH--NMeOMe A2 --
racemate 5-73 CH.sub.2CH.sub.2CF.sub.3 CH.sub.2-c-Pr
NH--N.dbd.CHNMeSMe A2 -- racemate 5-74 H CH.sub.2-c-Pr
N.dbd.CH--NMe.sub.2 A2 -- racemate
[0337]
6TABLE 6 Physical data and stereo- chemical No. R.sup.1
A.sup.2-R.sup.2 R.sup.3 A.sup.1 (X).sub.n information 6-1 CHFMe
3-furyl N.dbd.CHNMe.sub.2 A2 -- racemate 6-2 CHFMe 3-furyl
N.dbd.C(Me)(NMe.sub.2) A2 -- racemate 6-3 CHFMe 3-furyl
N.dbd.C(Et)(NMe.sub.2) A2 -- racemate 6-4 CHFMe 3-furyl
N.dbd.CHNEt.sub.2 A2 -- racemate 6-5 CFMe.sub.2 3-furyl
N.dbd.CMeNMe.sub.2 A2 -- racemate 6-6 CFMe.sub.2 3-furyl
N.dbd.CHNMe.sub.2 A2 -- racemate
[0338]
7TABLE 7 Physical data and stereochemical No. R.sup.1
A.sup.2-R.sup.2 R.sup.3 A.sup.1 (X).sub.n information 7-1
CFMe.sub.2 34 N.dbd.CHNMe.sub.2 A2 -- racemate 7-2 CFMe.sub.2 35
N.dbd.CHNMe.sub.2 A2 3-Me racemate 7-3 CFMe.sub.2 36
N.dbd.CHNMe.sub.2 A2 3,5-Me.sub.2 racemate
[0339]
8TABLE 8 Physical data and stereochemical No. R.sup.1
A.sup.2-R.sup.2 R.sup.3 A.sup.1 (X).sub.n information 8-1 c-Pr c-Pr
N.dbd.CHNMe.sub.2 A3 -- racemate 8-2 CFMe.sub.2 c-Pr
N.dbd.CHNMe.sub.2 A3 -- racemate, oil 8-3 CF.sub.3 c-Pr
N.dbd.CHNMe.sub.2 A3 3,5-Cl.sub.2 racemate 8-4 CF.sub.2CF.sub.3
c-Pr N.dbd.CHNMe.sub.2 A3 -- racemate 8-5 CFMe.sub.2 c-Pr
N.dbd.CHNMe.sub.2 A3 3-CF.sub.3 racemate 8-6 CFMe.sub.2 c-Pr
N.dbd.CHNMe.sub.2 A3 2-F racemate 8-7 CFMe.sub.2 c-Pr
N.dbd.CHNMe.sub.2 A3 4-F racemate 8-8 CFMe.sub.2 c-Pr
N.dbd.CHNMe.sub.2 A3 4-OCF.sub.3 racemate 8-9 CFMe.sub.2 c-Pr
N.dbd.CHNMe.sub.2 A3 4-Cl racemate 8-10 CH.sub.2F c-Pr
N.dbd.CHNEt.sub.2 A3 -- racemate 8-11 CFMe.sub.2 c-Pr
N.dbd.CHNEt.sub.2 A3 -- racemate, oil 8-12 CFMe.sub.2 c-Pr
N.dbd.CHNEt.sub.2 A3 4-F, 3-Me racemate 8-13 CFMe.sub.2 c-Pr
N.dbd.CHNEt.sub.2 A3 3-Et racemate 8-14 CHFMe c-Pr
N.dbd.CHNEt.sub.2 A3 -- racemate 8-15 CHFEt c-Pr N.dbd.CHNEt.sub.2
A3 -- racemate 8-16 CHFPr c-Pr N.dbd.CHNEt.sub.2 A3 -- racemate
8-17 CFMe.sub.2 c-Pr N.dbd.CH--NMe.sub.2 A3 3-Cl racemate 8-18
CHFMe c-Pr N.dbd.CH--NMe.sub.2 A3 3-Cl racemate 8-19 CHFEt c-Pr
N.dbd.CH--NMe.sub.2 A3 3-Cl racemate 8-20 CFMe.sub.2 c-Pr
N.dbd.C(Me)(NMe.sub.2) A3 3-F racemate, oil 8-21 CHFMe c-Pr
N.dbd.C(Me)(NMe.sub.2) A3 3-F racemate, oil 8-22 CHFEt c-Pr
N.dbd.C(Me)(NMe.sub.2) A3 3-F racemate 8-23 CHMe.sub.2 c-Pr
N.dbd.CH--NEt.sub.2 A3 3-OMe racemate 8-24 CFMe.sub.2 c-Pr
N.dbd.CH--NEt.sub.2 A3 3-OMe racemate 8-25 CHFMe c-Pr
N.dbd.CH--NEt.sub.2 A3 3-OMe racemate 8-26 CHFEt c-Pr
N.dbd.CH--NEt.sub.2 A3 3-OMe racemate 8-27 CFMe.sub.2 c-Pr
NH--CH.dbd.N--OH A3 -- racemate 8-28 CFMe.sub.2 c-Pr
NH--CH.dbd.N--NH.sub.2 A3 -- racemate, oil 8-29 CFMe.sub.2 c-Pr
NH--CH.dbd.N--NMe.sub.2 A3 -- racemate 8-30 CFMe.sub.2 c-Pr
N.dbd.CH(Me)(Ph) A3 -- racemate 8-31 CFMe.sub.2 c-Pr
N.dbd.CH(Ph).sub.2 A3 -- racemate 8-32 CFMe.sub.2 c-Pr
N.dbd.CH(2-Cl-C.sub.6H.sub.4).sub.2 A3 -- racemate 8-33 CFMe.sub.2
c-Pr N.dbd.CH(Me)(4-NO.sub.2-C.sub.6H.sub.4) A3 -- racemate 8-34
CFMe.sub.2 c-Pr N.dbd.CH(Et)(Ph) A3 -- racemate 8-35 CFMe.sub.2
c-Pr N.dbd.CH(n-Pr)(Ph) A3 -- racemate 8-36 CHFMe c-Pr
N.dbd.CH(3-Cl-C.sub.6H.sub.4) A3 -- racemate 8-37 CFMe.sub.2 c-Pr
N.dbd.CH(4-Cl-C.sub.6H.sub.4) A3 -- racemate, oil 8-38 CFMe.sub.2
c-Pr N.dbd.CH--NMe.sub.2 OA2 -- racemate 8-39 CMe.dbd.CH.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 OA2 -- racemate 8-40 CF.sub.3 c-Pr
N.dbd.CH--NMe.sub.2 OA2 -- racemate 8-41 CHF.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 OA2 -- racemate 8-42 CHF.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 OA2 -- racemate 8-43 CF.sub.3 c-Pr
N.dbd.CH--NMe.sub.2 OA2 3,5-Me.sub.2 racemate 8-44 CCl.sub.3 c-Pr
N.dbd.CH--NMe.sub.2 OA2 3-Et racemate 8-45 CFCe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 OA2 -- racemate 8-46 Me c-Pr
N.dbd.C(NMe.sub.2).sub.2 OA2 -- racemate 8-47 Me c-Pr
N.dbd.C(NEt.sub.2).sub.2 OA2 -- racemate 8-48 i-Pr c-Pr
N.dbd.C(NMe.sub.2)(NEt.sub.2) OA2 -- racemate 8-49 i-Bu c-Pr
N.dbd.C(NMe.sub.2)(NMeOMe) OA2 -- racemate 8-50 sec-Bu c-Pr
N.dbd.C(NEt.sub.2)(NEtOEt) OA2 -- racemate 8-51 n-Bu c-Pr
N.dbd.C(NMe.sub.2)(NMeSMe) OA2 -- racemate 8-52 CF.sub.2CHF.sub.2
c-Pr N.dbd.C(OMe)(NMeOMe) OA2 -- racemate 8-53 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 A3 -- R enantiomer 8-54 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 A3 -- S enantiomer 8-55 CFMe.sub.2 c-Pr
N.dbd.CHNEt.sub.2 A3 -- R enantiomer 8-56 CFMe.sub.2 c-Pr
N.dbd.CHNEt.sub.2 A3 -- S enantiomer 8-57 CFMe.sub.2 c-Pr
N.dbd.CHNMe.sub.2 A3 3-F racemate, oil 8-58 CHFMe c-Pr
N.dbd.CHNMe.sub.2 A3 3-F racemate, oil 8-59 CFMe.sub.2 c-Pr
N.dbd.CHNEt.sub.2 A3 3-F racemate, oil
[0340]
9TABLE 9 Physical data and stereo- chemical No. R.sup.1
A.sup.2-R.sup.2 R.sup.3 A.sup.1 (X).sub.n information 9-1
CFMe.sub.2 c-Bu N.dbd.CH--NMe.sub.2 A3 -- racemate 9-2 CHMe.sub.2
c-Bu N.dbd.CH--NMe.sub.2 A3 -- racemate 9-3 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 A3 -- racemate 9-4 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 OA2 -- racemate 9-5 CF.sub.3 c-Bu
N.dbd.C(Me)(NPr.sub.2) OA2 -- racemate
[0341]
10TABLE 10 Physical data and stereochemical No. R.sup.1
A.sup.2-R.sup.2 R.sup.3 A.sup.1 (X).sub.n information 10-1
CH.sub.2OEt c-Pr N.dbd.C(Ph)(NMe.sub.2) A4 -- racemate 10-2
4-Cl-C.sub.6H.sub.4 c-Pr N.dbd.C(Bu)(NMe.sub.2) A4 -- racemate 10-3
c-Pr c-Pr N.dbd.C(Me)(NEt.sub.2) A4 -- racemate 10-4 c-Bu c-Pr
N.dbd.CHN(CH.sub.2Ph).sub.2 A4 -- racemate 10-5 CFMe.sub.2 c-Pr
N.dbd.CHNMe.sub.2 A4 -- racemate 10-6 CFMe.sub.2 c-Pr
N.dbd.CHNMe.sub.2 OA3 -- racemate
[0342]
11TABLE 11 Physical data and stereochemical No. R.sup.1
A.sup.2-R.sup.2 R.sup.3 A.sup.1 (X).sub.n information 11-1 Me Ph
N.dbd.CH--NEt.sub.2 A2 -- racemate 11-2 Me Ph N.dbd.CH--NEt.sub.2
A2 3,5-Cl.sub.2 racemate 11-3 Me 4-CF.sub.3-C.sub.6H.sub.4
N.dbd.CH--NMe.sub.2 OA1 -- racemate 11-4 CFMeEt CH.sub.2Ph
N.dbd.CH--NMe.sub.2 OA1 -- racemate 11-5 CFMeEt 4-CN-C.sub.6H.sub.4
N.dbd.CH--NMe.sub.2 OA2 -- racemate
[0343]
12TABLE 12 Compounds of the formula 37 Physical data and
stereochemical No. R.sup.1 A.sup.2-R.sup.2 R.sup.3 Z (X).sub.n
information 12-1 CFMe.sub.2 c-Pr N.dbd.CH--NMe.sub.2 H -- racemate
12-2 CHFMe c-Pr N.dbd.CH--NMe.sub.2 H -- racemate 12-3 CFMe.sub.2
c-Pr N.dbd.CH--NMe.sub.2 H 3-Cl racemate 12-4 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 H 3-F racemate 12-5 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 H 3-CH.sub.3 racemate 12-6 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 H 3-OCH.sub.3 racemate 12-7 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 H 3-Cl racemate 12-8 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 H 3-F racemate 12-9 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 H 3-CH.sub.3 racemate 12-10 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 H 3-OCH.sub.3 racemate 12-11 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 F H racemate 12-12 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 F 3-Cl racemate 12-13 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 F 3-F racemate 12-14 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 F 3-Me racemate 12-15 CFMe.sub.2 c-Pr
N.dbd.CH--NMe.sub.2 F 3-OMe racemate 12-16 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 F -- racemate 12-17 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 F -- racemate 12-18 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 F -- racemate 12-19 CHFMe c-Pr
N.dbd.CH--NMe.sub.2 F -- racemate 12-20 CFMe.sub.2 c-Pr
N.dbd.CHNEt.sub.2 H -- racemate 12-21 CFMe.sub.2 c-Pr
N.dbd.C(Me)NEt.sub.2 H -- racemate 12-22 CFMe.sub.2 c-Pr
N.dbd.C(Me)NPr.sub.2 H -- racemate 12-23 CHFMe c-Pr
N.dbd.CH--NEt.sub.2 H -- racemate 12-24 CHFEt c-Pr
N.dbd.CH--NEt.sub.2 H -- racemate 12-25 CHFEt c-Pr
N.dbd.CH--NEt.sub.2 Me -- racemate 12-26 CHFMe c-Pr
N.dbd.CH--NEt.sub.2 Me -- racemate 12-27 CFMe c-Pr
N.dbd.CH--NEt.sub.2 Me -- racemate 12-28 CHF.sub.2 c-Pr
N.dbd.CH--NEt.sub.2 Et 3,5-(OEt).sub.2 racemate 12-29 CFMe.sub.2
c-Bu N.dbd.CH--NMe.sub.2 H -- racemate 12-30 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 H -- racemate 12-31 CHFEt c-Bu
N.dbd.CH--NMe.sub.2 H -- racemate 12-32 CHFPr c-Bu
N.dbd.CH--NMe.sub.2 H -- racemate 12-33 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 H -- racemate 12-34 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 F -- racemate 12-35 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 Cl -- racemate 12-36 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 Br -- racemate 12-37 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 Me -- racemate 12-38 CFMe.sub.2 c-Bu
N.dbd.CH--NMe.sub.2 Et -- racemate 12-39 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 H -- racemate 12-40 CHFMe c-Bu
N.dbd.CH--NMe.sub.2 F -- racemate 12-41 CHMe c-Bu
N.dbd.CH--NMe.sub.2 Me -- racemate 12-42 CFMe.sub.2 c-Bu
N.dbd.CH--Net.sub.2 H -- racemate 12-43 CHFEt c-Bu
N.dbd.CH--Net.sub.2 F -- racemate 12-44 CF.sub.3 c-Bu
N.dbd.CH--Net.sub.2 Me -- racemate 12-45 CF.sub.3 c-Bu
N.dbd.C(Me)(NMe.sub.2) H -- racemate 12-46 CF.sub.2Me c-Bu
N.dbd.C(Me)(NMe.sub.2) H -- racemate 12-47 CFMe.sub.2 c-Bu
N.dbd.C(Me)(NMe.sub.2) H -- racemate 12-48 CFMe.sub.2 c-Bu
N.dbd.C(Me)(NMe.sub.2) 4-F, 3-Me racemate 12-49 CFMe.sub.2 c-Bu
N.dbd.C(Et)(NEt.sub.2) 4-F, 3-Me racemate
B. FORMULATION EXAMPLES
[0344] a) A dust is obtained by mixing 10 parts by weight of a
compound of the formula (I) and 90 parts by weight of talc as inert
substance and comminuting the mixture in a hammer mill.
[0345] b) A wettable powder which is readily dispersible in water
is obtained by mixing 25 parts by weight of a compound of the
formula (I), 64 parts by weight of kaolin-containing quartz as
inert material, 10 parts by weight of potassium lignosulfonate and
1 part by weight of sodium oleoylmethyltaurate as wetter and
dispersant and grinding the mixture in a pinned-disk mill.
[0346] c) A dispersion concentrate which is readily dispersible in
water is obtained by mixing 20 parts by weight of a compound of the
formula (I) with 6 parts by weight of alkylphenol polyglycol ether
(.RTM.Triton X 207), 3 parts by weight of isotridecanol polyglycol
ether (8 EO) and 71 parts by weight of paraffinic mineral oil
(boiling range for example approx. 255 to over 277.degree. C.) and
grinding the mixture in a grinding-ball mill to a fineness of below
5 microns.
[0347] d) An emulsifiable concentrate is obtained from 15 parts by
weight of a compound of the formula (I), 75 parts by weight of
cyclohexanone as solvent and 10 parts by weight of oxethylated
nonylphenol as emulsifier.
[0348] e) Water-dispersible granules are obtained by mixing
13 75 parts by weight of a compound of the formula (I), 10 parts by
weight of calcium lignosulfonate, 5 parts by weight of sodium
laurylsulate, 3 parts by weight of polyvinyl alcohol and 7 parts by
weight of kaolin,
[0349] grinding the mixture on a pinned-disk mill and granulating
the powder in a fluidized bed by spraying on water of granulation
liquid.
[0350] f) Water-dispersible granules are also obtained by
homogenizing and precomminuting
14 25 parts by weight of a compound of the formula (I), 5 parts by
weight of 2,2'-dinaphthylmethane-6,6'-disulfonate, 5 parts by
weight of sodium oleoylmethyltaurate, 1 part by weight of polyvinyl
alcohol, 17 parts by weight of calcium carbonate and 50 parts by
weight of water
[0351] in a colloid mill, subsequently grinding the mixture in a
bead mill and atomizing and drying the resulting suspension in a
spray tower by means of a single-substance nozzle.
C. BIOLOGICAL EXAMPLES
[0352] 1. Pre-emergence herbicidal action
[0353] Seeds or rhizome pieces of monocotyledonous and
dicotyledonous weed plants are placed in sandy loam in plastic pots
and covered with soil. The compounds according to the invention,
which are formulated in the form of wettable powders or emulsion
concentrates, are then applied to the surface of the soil cover as
aqueous suspension or emulsion at various dosages with an
application rate of 600 to 800 1 of water per ha (converted).
[0354] After the treatment, the pots are placed into a greenhouse
and kept under good growth conditions for the weeds. The plant or
emergence damage is scored visually after the test plants have
emerged after an experimental time of 3 to 4 weeks by comparison
with untreated controls.
[0355] The compounds according to the invention show a very good
pre-emergence activity against a broad spectrum of grass weeds and
broad-leaved weeds. For example, compounds according to the
invention (see Examples A1 to A3 and compounds 2-1, 2-35, 2-36,
2-45, 2-55, 2-56, 3-1, 3-14, 3-25, 3-37, 3-38, 3-40, 3-41, 3-43,
3-44, 3-46, 3-47, 3-55, 3-56, 3-58, 3-59, 3-67, 3-68, 3-70, 3-71,
3-74, 3-85, 3-86, 3-124, 5-1, 5-40, 8-2, 8-11, 8-20, 8-21, 8-27 and
8-37 of Tables 1 to 12) effect a very good pre-emergence control on
harmful plants such as Stellaria media, Lolium multiforum,
Amaranthus retroflexus, Sinapis alba, Avena sativa and Setaria
viridis.
[0356] 2. Post-emergence herbicidal action
[0357] Seeds or rhizome pieces of monocotyledonous and
dicotyledonous weeds are placed in sandy loam in plastic pots,
covered with soil and grown in the greenhouse under good growth
conditions. Three weeks after sowing, the test plants are treated
in the three-leaf stage. Various dosages of the compounds according
to the invention, which are formulated as wettable powders or
emulsion concentrates, are sprayed to the green plant parts at an
application rate of 600 to 800 l of water per ha (converted). After
the test plants have been left to stand in the greenhouse for
approx. 3 to 4 weeks under optimal growth conditions, the effect of
the preparations is scored visually by comparison with untreated
controls. The compositions according to the invention also have a
good herbicidal post-emergence activity against a broad spectrum of
economically important grass weeds and broad-leaved weeds, for
example against harmful plants such as Sinapis alba, Echinochloa
crus-galli, Lolium multiflorum, Stellaria media, Cyperus iria,
Amaranthus retroflexus, Setaria viridis and Avena sativa when an
application rate of 1 kg and less active substance of the compounds
according to the invention (see Examples A1 to A3 and compounds
2-1, 2-35, 2-36, 2-45, 2-55, 2-56, 3-1, 3-14, 3-25, 3-37, 3-38,
3-40, 3-41, 3-43, 3-44, 3-46, 3-47, 3-55, 3-56, 3-58, 3-59, 3-67,
3-68, 3-70, 3-71, 3-74, 3-85, 3-86, 3-124, 5-1, 5-40, 8-2, 8-11,
8-20, 8-21, 8-27 and 8-37 of Tables 1 to 12) is applied
post-emergence per hectare.
[0358] 3. Action against harmful plants in rice
[0359] Transplanted and seeded rice and typical rice weeds
(broad-leaved and grass weeds) are grown in the greenhouse until
they have reached the three-leaf stage (Echinochloa crus-galli
1.5-leaves) under paddy rice conditions (flooding level of the
water: 2 - 3 cm) in closed plastic pots. They are then treated with
the compounds according to the invention. To this end, the
formulated active substances are suspended, dissolved or emulsified
in water and applied to the paddy water of the test plants at
various dosages by application by pouring. After the treatment has
been carried out in this way, the test plants are placed into the
greenhouse under optimal growth conditions and kept in this way
over the entire experimental period.
[0360] Approximately three weeks after application, the experiments
are evaluated by visually scoring the plant damage in comparison
with untreated controls. The compounds according to the invention
(see Examples A1 to A3 and compounds 2-1, 2-35, 2-36, 2-45, 2-55,
2-56, 3-1,3-14, 3-25, 3-37, 3-38, 3-40, 3-41, 3-43, 3-44, 3-46,
3-47, 3-55, 3-56, 3-58, 3-59, 3-67, 3-68, 3-70, 3-71, 3-74, 3-85,
3-86, 3-124, 5-1, 5-40, 8-2, 8-11, 8-20, 8-21, 8-27 and 8-37 of
Tables 1 to 12) show a very good herbicidal action against harmful
plants such as, for example, Cyperus monti, Echinochloa crusgalli
and Sagittaria pygmaea.
[0361] 4. Crop plant tolerance
[0362] In further greenhouse experiments seeds of a larger number
of crop plants and weeds are placed in sandy loam covered with
soil. Some of the pots are coated immediately as described in
Section 1, while the remaining pots are placed in the greenhouse
until the plants have developed two to three leaves and are then
sprayed with various dosages of the substances of formula (I)
according to the invention as described under Section 2. Four to
five weeks after the application and standing time in the
greenhouse, it is found by means of visual scoring that the
compounds according to the invention leave dicotyledonous crops
such as, for example, soybeans, cotton, oilseed rape, sugar beet
and potatoes unharmed when applied pre- and post-emergence, even at
high rates of active substance. In addition, some substances also
leave graminaceous crops such as, for example, barley, wheat, rye,
sorghum, maize or rice, unharmed. Some of the compounds of the
formula (I) show a high degree of selectivity and are therefore
suitable for controlling undesired vegetation in agricultural
crops.
* * * * *