|
New Page 1
1. A compound which is a 1-phenylpyrrolidin-2-one-3-carboxamide of the
formula I where the variables R.sup.1, R.sup.2, R.sup.3, X, Y, A, n, R.sup.a,
R.sup.b, R.sup.c, R.sup.d and R.sup.e are as defined below: R.sup.1 is hydrogen,
OH, Cl, Br, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, C(O)R.sup.4 or OC(O)R.sup.4;
R.sup.2 and R.sup.3 independently of one another are hydrogen,
C.sub.1-C.sub.10-alkyl, C.sub.3-C.sub.10-cycloalkyl,
C.sub.7-C.sub.10-polycycloalkyl, C.sub.3-C.sub.8-alkenyl,
C.sub.3-C.sub.10-alkynyl, C.sub.5-C.sub.10-cycloalkenyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4- -alkyl, phenyl or 3- to 7-membered
heterocyclyl, where the 9 last-mentioned groups may be unsubstituted, partially
or fully halogenated and/or substituted by 1, 2 or 3 radicals selected from the
group consisting of OH, CN, NO.sub.2, COOH, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.4-haloalkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, unsubstituted or substituted phenyl, COOR.sup.5,
NR.sup.6R.sup.7, C(O)NR.sup.8SO2R.sup.13, C(O)NR.sup.8R.sup.9 and 3- to
7-membered heterocyclyl, wherein each heterocyclyl may contain 1, 2 or 3
heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur, a
group NR.sup.10 and a group SO.sub.2, and, if appropriate, 1, 2 or 3 carbonyl
groups and/or thiocarbonyl groups as ring members; and/or may contain a
ring-fused phenyl ring which is unsubstituted or substituted; or R.sup.2 and
R.sup.3, together with the group N-(A).sub.n to which they are attached, form a
saturated 3- to 7-membered heterocycle which, in addition to the nitrogen atom,
may contain 1, 2 or a further 3 heteroatoms selected from the group consisting
of oxygen, nitrogen, sulfur and a group NR.sup.10 and, if appropriate, 1, 2 or 3
carbonyl groups and/or thiocarbonyl groups as ring members; R.sup.a, R.sup.b,
R.sup.c, R.sup.d and R.sup.e independently of one another are hydrogen, OH, CN,
NO.sub.2, halogen, C.sub.1-C.sub.10-alkyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalk- yl,
C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.4-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.4-haloalkylthio, C(O)R.sup.4,
COOR.sup.5, NR.sup.6R.sup.7, C(O)NR.sup.8R.sup.9, S(O).sub.2NR.sup.8R.sup.9,
S(O)R.sup.11, S(O).sub.2R.sup.11 or
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.6-alkyl; or two adjacent radicals R.sup.a
to R.sup.e, together with the atoms to which they are attached, form a 5-, 6- or
7-membered saturated or unsaturated ring which may contain one or two
heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and a
group NR.sup.10 as ring-forming atom and/or may carry one, two, three or four
radicals selected from the group consisting of halogen and
C.sub.1-C.sub.4-alkyl; X, Y independently of one another are oxygen or sulfur; n
is 0 or 1; A is O, S(O).sub.k or NR.sup.12, where k is 0, 1 or 2; R.sup.4,
R.sup.8, R.sup.9 independently of one another are hydrogen or
C.sub.1-C.sub.4-alkyl; R.sup.5, R.sup.11 are C.sub.1-C.sub.4-alkyl; R.sup.6,
R.sup.7 independently of one another are hydrogen, C.sub.1-C.sub.6-alkyl,
C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, C(O)R.sup.4, COOR.sup.5 or S(O).sub.2R.sup.11;
R.sup.10, R.sup.12 independently of one another are hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl or C.sub.3-C.sub.6-alkynyl; and
R.sup.13 is phenyl which is unsubstituted or carries 1, 2, 3 or 4 substituents,
where the substituents are selected from the group consisting of halogen, nitro,
cyano, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, COOR.sup.5, NR.sup.6R.sup.7 and
C(O)NR.sup.8R.sup.9; or an agriculturally useful salt thereof.
2. A compound as claimed in claim 1 in which R.sup.2 and R.sup.3 independently
of one another are hydrogen, C.sub.1-C.sub.10-alkyl,
C.sub.3-C.sub.10-cycloalkyl, C.sub.3-C.sub.8-alkenyl, C.sub.3-C.sub.8-alkynyl,
C.sub.5-C.sub.10-cycloalkenyl, C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl,
phenyl or 3- to 7-membered heterocyclyl, where the 8 last-mentioned groups may
be unsubstituted, partially or fully halogenated and/or substituted by 1, 2 or 3
radicals selected from the group consisting of OH, CN, NO.sub.2, COOH,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.1-C.sub.6-alkylth- io, C.sub.1-C.sub.4-haloalkylthio, unsubstituted or
substituted phenyl, COOR.sup.5, NR.sup.6R.sup.7, C(O)NR R.sup.9, wherein each
heterocyclyl may contain 1, 2 or 3 heteroatoms selected from the group
consisting of oxygen, nitrogen, sulfur and a group NR.sup.10 and, if
appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups as ring
members; or R.sup.2 and R.sup.3, together with the group N-(A).sub.n to which
they are attached, form a saturated 3- to 7-membered heterocycle which, in
addition to the nitrogen atom, may contain 1, 2 or a further 3 heteroatoms
selected from the group consisting of oxygen, nitrogen, sulfur and a group
NR.sup.10 and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl
groups as ring members.
3. A compound as claimed in claim 1 wherein R.sup.1 is hydrogen.
4. A compound as claimed in claim 1 wherein R.sup.3 is hydrogen or
C.sub.1-C.sub.4-alkyl.
5. A compound as claimed in claim 1 wherein R.sup.2 is C.sub.1-C.sub.6-alkyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl,
C.sub.5-C.sub.6-cycloal- kenyl, substituted or unsubstituted phenyl,
C.sub.3-C.sub.6-cycloalkyl-C.s- ub.1-.sub.4-alkyl, where C.sub.1-C.sub.6-alkyl
and C.sub.3-C.sub.6 cycloalkyl may be partially or fully halogenated and/or may
contain a at least one radical selected from the group consisting of
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, unsubstituted or substituted phenyl, COOR.sup.5,
NR.sup.6R.sup.7 and C(O)NR.sup.8R.sup.9.
6. A compound as claimed in claim 1 wherein X and Y represent oxygen.
7. A compound as claimed in claim 1 wherein n=0.
8. A compound as claimed in claim 1 wherein the radicals R.sup.a, R.sup.b,
R.sup.c, R.sup.d and R.sup.e are selected from the group consisting of hydrogen,
halogen, CN, C.sub.1-C.sub.4-alkyl, OCH.sub.3, CF.sub.3, CHF.sub.2, OCF.sub.3
and OCHF.sub.2.
9. A compound as claimed in claim 1 wherein not more than 3 of the radicals
R.sup.a, R.sup.b, R.sup.c, R.sup.d and R.sup.e are different from hydrogen.
10. A compound as claimed in claim 1 wherein 2 or 3 of the radicals R.sup.a,
R.sup.b, R.sup.c, R.sup.d and R.sup.e are different from hydrogen.
11. A compound as claimed in claim 9 wherein the radicals R.sup.a and R.sup.e
represent hydrogen.
12. A composition, comprising a herbicidally effective amount of at least
compound as claimed in claim 1, and at least one inert liquid and/or solid
carrier, and, if desired, at least one surfactant.
13. A method for controlling unwanted vegetation, which comprises allowing a
herbicidally effective amount of at least one compound as claimed in claim 1 to
act on plants, their habitat or on seed.
14. A method for controlling unwanted vegetation, comprising applying to plants,
their habitat or to their seed a herbicidally effective amount of at least one
compound of claim 1.
15. The method of claim 14, wherein said compound is applied at an application
rate of from 0.001 to 3.0 kg/ha.
16. The method of claim 15, wherein the application rate of said compound is
0.01 to 1.0 kg/ha.
17. A compound of claim 1, wherein n is 1 and A, is oxygen, a group N--R.sup.12,
where R.sup.12=hydrogen or alkyl, or a group SO.sub.2.
18. A compound of claim 1, wherein R.sup.a, R.sup.b, R.sup.c, R.sup.d, R.sup.e
are independently hydrogen, halogen, CN, 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.
19. A compound of claim 1, wherein R.sup.1 is hydrogen, OH, Cl, Br,
C.sub.1-C.sub.6-alkyl or OC(O)R.sup.4.
20. A compound of claim 1, wherein R.sup.2 is C.sub.1-C.sub.10-alkyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-alkenyl, C.sub.3-C.sub.8-alkynyl,
C.sub.3-C.sub.8-cycloalkyl, C.sub.5-C.sub.8-cycloalkenyl or
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.- 4-alkyl, where C.sup.1-C.sub.10-alkyl
and C.sub.3-C.sub.8-cycloalkyl may be partially or fully halogenated and/or may
carry one or two radicals selected from the group consisting of
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sup.1-C.sub.4-haloalkylthio, unsubstituted or substituted phenyl, COOR.sup.5,
NR.sup.6R.sup.7, C(O)NR.sup.8R.sup.9, phenyl which may be unsubstituted or
substituted by 1, 2 or 3 substituents selected from the group consisting of
halogen, nitro, OH, CN, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, unsubstited or substituted phenyl, COOR.sup.5,
NR.sup.6R.sup.7 and C(O)NR.sup.8R.sup.9.
21. A compound of formula (Ia) wherein R.sup.b, R.sup.c, R.sup.d independently
of one another are hydrogen, OH, CN, NO.sub.2, halogen, C.sub.1-C.sub.10-alkyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.1-C.sub.6-haloalk- yl, C.sub.2-C.sub.6-haloalkenyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, C(O)R.sup.4, COOR.sup.5, NR.sup.6R.sup.7,
C(O)NR.sup.8R.sup.9, S(O).sub.2NR.sup.8R.sup.9, S(O)R.sup.11, S(O).sub.2R.sup.11
or C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.6-alkyl; and R.sup.2 is hydrogen,
C.sub.1-C.sub.10-alkyl, C.sub.3-C.sub.10-cycloalkyl,
C.sub.7-C.sub.10-polycycloalkyl, C.sub.3-C.sub.8-alkenyl,
C.sub.3-C.sub.10-alkynyl, C.sub.5-C.sub.10-cycloalkenyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, phenyl or 3- to 7-membered
heterocyclyl, where the 9 last-mentioned groups may be unsubstituted, partially
or fully halogenated and/or contain 1, 2 or 3 radicals selected from the group
consisting of OH, CN NO.sub.2, COOH, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.4-haloalkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.4-haloalkylthio, unsubstituted or substituted phenyl, COOR.sup.5,
NR.sup.6R.sup.7, C(O)NR.sup.8SO.sub.2R.sup.13, C(O)NR.sup.8R.sup.9 and 3- to
7-membered heterocyclyl, wherein each hetercyclyl may contain 1, 2 or 3
heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur, a
group NR.sup.10 and a group SO.sub.2, and, if appropriate, 1, 2 or 3 carbonyl
groups and/or thiocarbonyl groups as ring members; and/or may contain a
ring-fused phenyl ring which is unsubstituted or substituted.
[0001] The present invention relates to 1-phenylpyrrolidin-2-one-3-carboxa-
mides and their agriculturally useful salts, to compositions comprising such
compounds and to the use of the 1-phenylpyrrolidin-2-one-3-carboxami- des, of
their salts or of compositions comprising them as herbicides.
[0002] WO 95/33719 describes 1-arylthiazolidinones, 1-aryloxazolidinones and
1-arylpyrrolidinones of the formula: where A is an aromatic or heteroaromatic
radical, n is 0 or 1, x is in particular S, O or CH.sub.2, Y is in particular S,
O, CH.sub.2 or CH(CH.sub.3) or a group NR.sup.6, Z is in particular NH or O,
R.sup.1 is preferably selected from unsubstituted or substituted alkyl, alkenyl,
alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted
phenyl, benzyl or hetaryl, acyl, alkoxycarbonylalkyl and silyl, R.sup.2 and
R.sup.3 are in particular hydrogen and R.sup.6 is inter alia hydrogen, formyl,
unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl or
unsubstituted or substituted aryl.
[0003] WO 95/33718 describes 1-phenylpyrrolidinethiones having herbicidal
activity which, in the 3-position of the pyrrolidinethione ring, contain a group
O--C(O)--NR.sup.1R.sup.2 where R.sup.1R.sup.2 are, for example, hydrogen, an
unsubstituted or substituted hydrocarbon radical or hetaryl, or together with
the nitrogen atom to which they are attached form a heterocycle.
[0004] Furthermore, U.S. Pat. No. 4,874,422 discloses herbicidally active
1-phenylpyrrolidin-2-one-3-carboxamides of the formula A where X is hydrogen or
halogen, Y and Z independently of one another are O or S, n is 0 or 1, R.sup.1
is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, phenyl, halophenyl,
benzyl, halobenzyl, or alkyl which is substituted by alkoxy, alkylthio, phenyl,
hydroxyl or cyano, R.sup.2 is hydrogen or alkyl, R.sup.3 is alkyl or alkenyl and
R.sup.4 is selected from the group consisting of hydrogen, halogen, methyl,
trifluoromethyl, 1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyloxy,
difluoromethoxy, trifluoromethoxy, methylsulfanyl, methylsulfinyl,
methylsulfonyl, methoxyiminomethyl, methoxyimino-1-ethyl, benzyloxyiminomethyl
and benzyloxyimino-1-ethyl.
[0005] The herbicidal activity of the 1-arylpyrrolidinones described in the
prior art is not always satisfactory. Their selectivity for harmful plants is
unsatisfactory, too. In particular, even at low application rates, such
herbicides tend to interfere with the generation of chlorophyll even in crop
plants, which is undesirable in principle and may lead to yield losses.
[0006] It is an object of the present invention to provide novel herbicidally
active compounds which allow a better targeted control of unwanted plants than
the known herbicides. Advantageously, the novel herbicides should be highly
active against harmful plants. Moreover, high compatibility with crop plants is
desirable. Moreover, the compounds should have no adverse effect on the
chlorophyll synthesis in crop plants.
[0007] We have found that this object is achieved by
1-phenylpyrrolidin-2-one-3-carboxamides of the formula I defined below and their
agriculturally useful salts: where the variables R.sup.1, R.sup.2, R.sup.3, X,
Y, A, n, R.sup.a, R.sup.b, R.sup.c, R.sup.d and R.sup.e are as defined below:
[0008] R.sup.1 is hydrogen, OH, Cl, Br, C.sub.1-C.sub.6-alkyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl,
C(O)R.sup.4 or OC(O)R.sup.4; [0009] R.sup.2 and R.sup.3 independently of one
another are hydrogen, C.sub.1-C.sub.10-alkyl, C.sub.3-C.sub.10-cycloalkyl,
C.sub.7-C.sub.10-polycycloalkyl, C.sub.3-C.sub.8-alkenyl,
C.sub.3-C.sub.10-alkynyl, C.sub.5-C.sub.10-cycloalkenyl,
C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, phenyl or 3- to 7-membered
heterocyclyl, where the 9 last-mentioned groups may be unsubstituted, partially
or fully halogenated and/or contain 1, 2 or 3 radicals selected from the group
consisting of OH, CN, NO.sub.2, COOH, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.4-haloalkoxy,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.4-haloalkyl-thio, unsubstituted or substituted phenyl, COOR.sup.5,
NR.sup.6R.sup.7, C(O)NR.sup.8SO.sub.2R.sup.13, C(O)NR.sup.8R.sup.9 and 3- to
7-membered heterocyclyl, and each heterocyclyl may contain 1, 2 or 3 heteroatoms
selected from the group consisting of oxygen, nitrogen, sulfur, a group
NR.sup.10 and a group SO.sub.2, and, if appropriate, 1, 2 or 3 carbonyl groups
and/or thiocarbonyl groups as ring members; and/or may contain a ring-fused
phenyl ring which is unsubstituted or substituted; or [0010] R.sup.2 and R.sup.3
with the group N-(A).sub.n to which they are attached form a saturated 3- to
7-membered heterocycle which, in addition to the nitrogen atom, may contain 1, 2
or a further 3 heteroatoms selected from the group consisting of oxygen,
nitrogen, sulfur and a group NR.sup.10 and, if appropriate, 1, 2 or 3 carbonyl
groups and/or thiocarbonyl groups as ring members; [0011] R.sup.a, R.sup.b,
R.sup.c, R.sup.d and R.sup.e independently of one another are hydrogen, OH, CN,
NO.sub.2, halogen, C.sub.1-C.sub.10-alkyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalk- yl,
C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.4-haloalkoxy,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.4-haloalkylthio, C(O)R.sup.4,
COOR.sup.5, NR.sup.6R.sup.7, C(O)NR.sup.8R.sup.9, S(O).sub.2NR.sup.8R.sup.9,
S(O)R.sup.11, S(O).sub.2R.sup.11 or
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.6-alkyl; or [0012] two adjacent radicals
R.sup.a to R.sup.e together with the atoms to which they are attached form a 5-,
6- or 7-membered saturated or unsaturated ring which may contain one or two
heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and a
group NR.sup.10 as ring-forming atom and/or may carry one, two, three or four
radicals selected from the group consisting of halogen and
C.sub.1-C.sub.4-alkyl; [0013] X, Y independently of one another are oxygen or
sulfur; [0014] n is 0 or 1; [0015] A is O, S(O).sub.k or NR.sup.12, where k is
0, 1 or 2; [0016] R.sup.4, R.sup.8, R.sup.9 independently of one another are
hydrogen or C.sub.1-C.sub.4-alkyl; [0017] R.sup.5, R.sup.11 are
C.sub.1-C.sub.4-alkyl; [0018] R.sup.6, R.sup.7 independently of one another are
hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl,
C.sub.3-C.sub.6-alkynyl, C(O)R.sup.4, COOR.sup.5 or S(O).sub.2R.sup.11; [0019]
R.sup.10, R.sup.12 independently of one another are hydrogen,
C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl or C.sub.3-C.sub.6-alkynyl- ; and
[0020] R.sup.13 is phenyl which is unsubstituted or carries 1, 2, 3 or 4
substituents, where the substituents are selected from the group consisting of
halogen, nitro, cyano, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, COOR.sup.5,
NR.sup.6R.sup.7 and C(O)NR.sup.8R.sup.9.
[0021] Accordingly, the present invention relates to
1-phenyl-pyrrolidin-2-one-3-carboxamides of the formula I and their
agriculturally useful salts.
[0022] Moreover, the present invention relates to [0023] the use of compounds I
and/or their salts as herbicides; [0024] crop protection compositions comprising
at least one 1-phenylpyrrolidin-2-one-3-carboxami- de of the formula I and/or at
least one agriculturally useful salt of I as active substances; and [0025]
methods for controlling unwanted vegetation, which comprises allowing a
herbicidally effective amount of at least one
1-phenylpyrrolidin-2-one-3-carboxamide of the formula I or an agriculturally
useful salt of I to act on plants, their habitat or on seed.
[0026] Depending on the substitution pattern, the compounds of the formula I may
contain one or more centers of chirality, in which case they are present as
mixtures of enantiomers or diastereomers. The invention provides both the pure
enantiomers or diastereomers and their mixtures. The invention also provides
tautomers of compounds of the formula I.
[0027] If R.sup.1 represents hydrogen, the 1-phenylpyrrolidin-2-one-3-carb-
oxamides of the formula I according to the invention can be present in the form
of their agriculturally useful salts. In general, agriculturally useful salts
are the salts of those bases or cations which have no adverse effect on the
herbicidal action of the compounds I. Thus, suitable basic salts are in
particular the salts of the alkali metals, preferably of sodium and potassium,
of the alkaline earth metals, preferably of calcium, magnesium and barium, and
of the transition metals, preferably of manganese, copper, zinc and iron, and
also ammonium salts where the ammonium ion may, if desired, carry one to four
C.sub.1-C.sub.4-alkyl substituents, C.sub.1-C.sub.4-hydroxyalkyl substituents,
C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl substituents and/or one phenyl or
benzyl substituent, preferably diisopropylammonium, tetramethylammonium,
tetrabutylammonium, trimethylbenzylammonium, trimethyl-2-hydroxyethylammonium,
bis(2-hydroxyethyl)methylammonium, tris(2-hydroxyethyl)ammonium,
bis(2-hydroxyethyl)-dimethylammonium, tris(2-hydroxyethyl)methylammonium,
furthermore phosphonium ions, sulfonium ions, preferably
tri(C.sub.1-C.sub.4-alkyl)sulfonium, and sulfoxonium ions, preferably
tri(C.sub.1-C.sub.4-alkyl)sulfoxonium.
[0028] The organic moieties mentioned in the definition of the substituents
R.sup.1 to R.sup.12 or as radicals on heterocyclic rings are--like the term
halo--collective terms for individual listings of the individual group members.
All carbon chains, i.e. all alkyl, haloalkyl, cyanoalkyl, aminoalkyl,
aminocarbonylalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl,
alkylsulfonyl, alkynyl and alkenyl moieties, may be straight-chain or branched.
Halogenated substituents preferably carry one to five identical or different
halogen atoms. The term halo denotes in each case fluorine, chlorine, bromine or
iodine.
[0029] Examples of other meanings are: [0030] C.sub.1-C.sub.4-alkyl: for example
methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or
1,1-dimethylethyl; [0031] C.sub.1-C.sub.6-alkyl: C.sub.1-C.sub.4-alkyl as
mentioned above and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl,
3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,
1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,
4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,
2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,
2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or
1-ethyl-3-methylpropyl; [0032] C.sub.1-C.sub.10-alkyl: C.sub.1-C.sub.6-alkyl as
mentioned above and also, for example, n-heptyl, 2-heptyl, 2-methylhexyl, n-octyl,
1-methylheptyl, 2-ethylhexyl, n-nonyl, 2-nonyl, n-decyl, 2-decyl, 2-propylheptyl
and the like; [0033] C.sub.1-C.sub.4-haloalkyl: a C.sub.1-C.sub.4-alkyl radical
as mentioned above which is partially or fully substituted by fluorine,
chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl,
trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,
chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl,
2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,
2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,
2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl,
2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,
2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl,
3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl,
2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,
1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl,
4-chlorobutyl, 4-bromobutyl or nonafluorobutyl; in particular difluoromethyl,
trifluoromethyl; [0034] C.sub.1-C.sub.6-haloalkyl: C.sub.1-C.sub.4-haloalkyl as
mentioned above and also 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl,
5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,
6-iodohexyl or dodecafluorohexyl; [0035] C.sub.1-C.sub.2-fluoroalkyl:
C.sub.1-C.sub.2-alkyl which carries 1, 2, 3, 4 or 5 fluorine atoms, for example
difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl,
2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl and pentafluoroethyl; [0036]
C.sub.1-C.sub.2-fluoroalkoxy: C.sub.1-C.sub.2-alkoxy which carries 1, 2, 3, 4 or
5 fluorine atoms, for example difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy,
2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy and
pentafluoroethoxy; [0037] C.sub.1-C.sub.4-alkoxy: for example methoxy, ethoxy,
n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or
1,1-dimethylethoxy; [0038] C.sub.1-C.sub.6-alkoxy: C.sub.1-C.sub.4-alkoxy as
mentioned above and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy,
3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,
1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy,
4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,
2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy,
2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy,
1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy; [0039]
C.sub.1-C.sub.4-haloalkoxy: a C.sub.1-C.sub.4-alkoxy radical as mentioned above
which is partially or fully substituted by fluorine, chlorine, bromine and/or
iodine, i.e., for example, OCH.sub.2F, OCHF.sub.2, OCF.sub.3, OCH.sub.2Cl,
OCH(Cl).sub.2, OC(Cl).sub.3, chlorofluoromethoxy, dichlorofluoromethoxy,
chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy,
2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,
2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,
2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC.sub.2F.sub.5,
2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,
2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,
3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,
OCH.sub.2--C.sub.2F.sub.5- , OCF.sub.2--C.sub.2F.sub.5,
1-(CH.sub.2F)-2-fluoroethoxy, 1-(CH.sub.2Cl)-2-chloroethoxy,
1-(CH.sub.2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or
nonafluorobutoxy, preferably OCHF.sub.2 or OCHF.sub.3; [0040]
C.sub.1-C.sub.4-alkoxy-C.sub- .1-C.sub.6-alkyl: C.sub.1-C.sub.6-alkyl which is
substituted by C.sub.1-C.sub.6-alkoxy--as mentioned above--, i.e., for example,
CH.sub.2--OCH.sub.3, CH.sub.2--OC.sub.2H.sub.5, n-propoxymethyl,
CH.sub.2--OCH(CH.sub.3) 2, n-butoxymethyl, (1-methylpropoxy)methyl,
(2-methylpropoxy)methyl, CH.sub.2--OC(CH.sub.3).sub.3, 2-(methoxy)ethyl,
2-(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl,
2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl,
2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(n-propoxy)propyl,
2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl,
2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl,
3-(ethoxy)propyl, 3-(n-propoxy)propyl, 3-(1-methylethoxy)propyl,
3-(n-butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,
3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,
2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl,
2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl,
3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl,
3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,
3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,
4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl,
4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl, 4-(1,1-dimethylethoxy)butyl,
2-(1-methylethoxy)pentyl, 2-(n-butoxy)pentyl, 2-(1-methylpropoxy)pentyl,
2-(2-methylpropoxy)pentyl, 2-(1,1-dimethylethoxy)pentyl, 3-(methoxy)pentyl,
3-(ethoxy)pentyl, 3-(n-propoxy)pentyl, 3-(1-methylethoxy)pentyl,
3-(n-butoxy)pentyl, 3-(1-methylpropoxy)pentyl, 3-(2-methylpropoxy)pentyl,
3-(1,1-dimethylethoxy)pentyl, 4-(methoxy)pentyl, 4-(ethoxy)pentyl,
4-(n-propoxy)pentyl, 4-(1-methylethoxy)pentyl, 4-(n-butoxy)pentyl,
4-(1-methylpropoxy)pentyl, 4-(2-methylpropoxy)pentyl,
4-(1,1-dimethylethoxy)pentyl, 4-(methoxy)pentyl, 5-(ethoxy)pentyl,
5-(n-propoxy)pentyl, 5-(1-methylethoxy)pentyl, 5-(n-butoxy)pentyl,
5-(1-methylpropoxy)pentyl, 5-(2-methylpropoxy)pentyl,
5-(1,1-dimethylethoxy)pentyl, 2-(1-methylethoxy)hexyl, 2-(n-butoxy)hexyl,
2-(1-methylpropoxy)hexyl, 2-(2-methylpropoxy)hexyl, 2-(1,1-dimethylethoxy)hexyl,
3-(methoxy)hexyl, 3-(ethoxy)hexyl, 3-(n-propoxy)hexyl, 3-(1-methylethoxy)hexyl,
3-(n-butoxy)hexyl, 3-(1-methylpropoxy)hexyl, 3-(2-methylpropoxy)hexyl
3-(1,1-dimethylethoxy)hexyl, 4-(methoxy)hexyl, 4-(ethoxy)hexyl,
4-(n-propoxy)hexyl, 4-(1-methylethoxy)hexyl, 4-(n-butoxy)hexyl,
4-(1-methylpropoxy)hexyl, 4-(2-methylpropoxy)hexyl, 4-(1,1-dimethylethoxy)hexyl,
4-(methoxy)hexyl, 5-(ethoxy)hexyl, 5-(n-propoxy)hexyl, 5-(1-methylethoxy)hexyl,
5-(n-butoxy)hexyl, 5-(1-methylpropoxy)hexyl, 5-(2-methylpropoxy)hexyl,
5-(1,1-dimethylethoxy)hexyl, 6-(ethoxy)hexyl, 6-(n-propoxy)hexyl,
6-(1-methylethoxy)hexyl, 6-(n-butoxy)hexyl, 6-(1-methylpropoxy)hexyl,
6-(2-methylpropoxy)hexyl, 6-(1,1-dimethylethoxy)hexyl; [0041]
C.sub.1-C.sub.4-alkylthio: an alkylsulfanyl radical having 1 to 4 carbon atoms,
for example SCH.sub.3, SC.sub.2H.sub.5, SCH.sub.2--C.sub.2H.sub.5,
SCH(CH.sub.3).sub.2, n-butylthio, SCH(CH.sub.3)--C.sub.2H.sub.5,
SCH.sub.2--CH(CH.sub.3) 2 or SC(CH.sub.3) 3; [0042] C.sub.1-C.sub.6-alkylthio:
C.sub.1-C.sub.4-alkylthio as mentioned above and also, for example, pentylthio,
1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio,
1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,
1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,
1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,
2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,
1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,
1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or
1-ethyl-2-methylpropylthio; [0043] C.sub.1-C.sub.4-haloalkylthio: a
C.sub.1-C.sub.4-alkylthio radical as mentioned above which is partially or fully
substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example,
fluoromethylthio, difluoromethylthio, trifluoromethylthio,
chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio,
2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio,
2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio- ,
2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,
2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio,
3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio,
3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,
2,3-dichloropropylthio, 3,3,3-trifluoropropylthio- , 3,3,3-trichloropropylthio,
2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio,
1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio,
1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio,
4-bromobutylthio or nonafluorobutylthio; [0044] phenyl-C.sub.1-C.sub.4-alkyl:
for example benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl,
2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl,
3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl,
3-phenylbut-2-yl, 4-phenylbut-2-yl, 1-(benzyl)eth-1-yl,
1-(benzyl)-1-(methyl)eth-1-yl or 1-(benzyl)prop-1-yl; [0045]
C.sub.2-C.sub.6-alkenyl: a monounsaturated aliphatic hydrocarbon radical having
2 to 6 and in particular 2 to 4 carbon atoms, for example ethenyl,
prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl,
buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl,
1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl,
penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl,
3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl,
3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,
3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl,
1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl,
hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl,
1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl,
4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl,
3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl,
2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,
1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl,
4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,
1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,
1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,
2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl,
2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl,
1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,
2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,
1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl,
1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl; [0046]
C.sub.3-C.sub.8-alkenyl: an aliphatic hydrocarbon radical which contains a
C.dbd.C double bond and has 3 to 8, preferably 3 to 6 and in particular 3 or 4
carbon atoms as mentioned above, which is preferably not attached via a carbon
atom of the double bond, for example one of the radicals mentioned under
C.sub.2-C.sub.6-alkenyl and also 1-hepten-3-yl, 1-hepten-4-yl, 1-hepten-5-yl,
1-hepten-6-yl, 1-hepten-7-yl, 3-hepten-1-yl, 2-hepten-4-yl, 3-hepten-5-yl,
3-hepten-6-yl, 3-hepten-7-yl, 1-octen-3-yl, 1-octen-4-yl, 1-octen-5-yl,
1-octen-6-yl, 1-octen-7-yl, 1-octen-8-yl, 3-octen-1-yl, 2-octen-1-yl,
2-octen-4-yl, 3-octen-5-yl, 3-octen-6-yl, 3-octen-7-yl, 3-octen-8-yl and the
like; [0047] C.sub.2-C.sub.6-haloalke- nyl: C.sub.2-C.sub.6-alkenyl as mentioned
above which is partially or fully substituted by fluorine, chlorine, and/or
bromine, i.e., for example, 2-chlorovinyl, 2-chloroallyl, 3-chloroallyl,
2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl,
2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl,
3,3-dibromoallyl, 2,3,3-tribromoallyl and 2,3-dibromobut-2-enyl; [0048]
C.sub.2-C.sub.6-alkynyl: an aliphatic hydrocarbon radical which contains a C--C
triple bond and has 2 to 6 and in particular 2 to 4 carbon atoms: for example
ethynyl, propargyl (2-propynyl), 1-propynyl, but-1-yn-3-yl, but-1-yn-4-yl,
but-2-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl,
pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl,
hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl,
hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl,
3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl,
4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl; [0049]
C.sub.3-C.sub.10-alkynyl: an aliphatic hydrocarbon radical which contains a
triple bond and has 3 to 10, preferably 3 to 6 and in particular 3 or 4 carbon
atoms as mentioned above, which is preferably not attached via a carbon atom of
the triple bond, for example one of the radicals mentioned under
C.sub.2-C.sub.6-alkynyl and also 1-heptyn-3-yl, 1-heptyn-4-yl, 1-heptyn-5-yl,
1-heptyn-6-yl, 1-heptyn-7-yl, 3-heptyn-1-yl, 2-heptyn-4-yl, 3-heptyn-5-yl,
3-heptyn-6-yl, 3-heptyn-7-yl, 1-octyn-3-yl, 1-octyn-4-yl, 1-octyn-5-yl,
1-octyn-6-yl, 1-octyn-7-yl, 1-octyn-8-yl, 3-octyn-1-yl, 2-octyn-1-yl,
2-octyn-4-yl, 3-octyn-5-yl, 3-octyn-6-yl, 3-octyn-7-yl, 3-octyn-8-yl and the
like; [0050] C.sub.3-C.sub.10-cycloalkyl: a monocyclic hydrocarbon radical
having 3 to 10 carbon atoms, in particular 3 to 8 carbon atoms and especially 3
to 6 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
cycloheptyl or cyclooctyl; [0051] C.sub.7-C.sub.10-polycycloalkyl: a bicyclic,
tricyclic or tetracyclic hydrocarbon radical having 7 to 10 carbon atoms, for
example bicyclo[2.2.1]-hept-1-yl, bicyclo[2.2.1]hept-2-yl,
bicyclo[2.2.1]hept-7-yl, bicyclo[2.2.2]oct-1-yl, bicyclo[2.2.2]oct-2-yl or
adamantan-1-yl; [0052] C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alk- yl:
C.sub.1-C.sub.4-alkyl which carries a C.sub.3-C.sub.8-cycloalkyl radical as
defined above, for example cyclopropylmethyl, 1-cyclopropylethyl,
2-cyclopropylethyl, 1-cyclopropylprop-1-yl, 2-cyclopropylprop-1-yl,
3-cyclopropylprop-1-yl, 1-cyclopropylbut-1-yl, 2-cyclopropylbut-1-yl,
3-cyclopropylbut-1-yl, 4-cyclopropylbut-1-yl, 1-cyclopropylbut-2-yl,
2-cyclopropylbut-2-yl, 3-cyclopropylbut-2-yl, 3-cyclopropylbut-2-yl,
4-cyclopropylbut-2-yl, 1-(cyclopropylmethyl)eth-1-- yl,
1-(cyclopropylmethyl)-1-(methyl)eth-1-yl, 1-(cyclopropylmethyl)prop-1-- yl,
cyclobutylmethyl, 1-cyclobutylethyl, 2-cyclobutylethyl, 1-cyclobutylprop-1-yl,
2-cyclobutylprop-1-yl, 3-cyclobutylprop-1-yl, 1-cyclobutylbut-1-yl,
2-cyclobutylbut-1-yl, 3-cyclobutylbut-1-yl, 4-cyclobutylbut-1-yl,
1-cyclobutylbut-2-yl, 2-cyclobutylbut-2-yl, 3-cyclobutylbut-2-yl,
4-cyclobutylbut-2-yl, 1-(cyclobutylmethyl)eth-1-yl,
1-(cyclobutylmethyl)-1-(methyl)eth-1-yl, 1-(cyclobutylmethyl)prop-1-yl,
cyclopentylmethyl, 1-cyclopentylethyl, 2-cyclopentylethyl,
1-cyclopentylprop-1-yl, 2-cyclopentylprop-1-yl, 3-cyclopentylprop-1-yl,
1-cyclopentylbut-1-yl, 2-cyclopentylbut-1-yl, 3-cyclopentylbut-1-yl,
4-cyclopentylbut-1-yl, 1-cyclopentylbut-2-yl, 2-cyclopentylbut-2-yl,
3-cyclopentylbut-2-yl, 3-cyclopentylbut-2-yl, 4-cyclopentylbut-2-yl,
1-(cyclopentylmethyl)eth-1-yl, 1-(cyclopentylmethyl)-1-(methyl)eth-1-yl,
1-(cyclopentylmethyl)prop-1-yl, cyclohexylmethyl, 1-cyclohexylethyl,
2-cyclohexylethyl, 1-cyclohexylprop-1-yl, 2-cyclohexylprop-1-yl,
3-cyclohexylprop-1-yl, 1-cyclohexylbut-1-yl, 2-cyclohexylbut-1-yl,
3-cyclohexylbut-1-yl, 4-cyclohexylbut-1-yl, 1-cyclohexylbut-2-yl,
2-cyclohexylbut-2-yl, 3-cyclohexylbut-2-yl, 4-cyclohexylbut-2-yl,
1-(cyclohexylmethyl)eth-1-yl, 1-(cyclohexylmethyl)-1-(methyl)eth-1-yl,
1-(cyclohexylmethyl)prop-1-yl, cycloheptylmethyl, 1-cycloheptylethyl,
2-cycloheptylethyl, 1-cycloheptylprop-1-yl, 2-cycloheptylprop-1-yl,
3-cycloheptylprop-1-yl, 1-cycloheptylbut-1-yl, 2-cycloheptylbut-1-yl,
3-cycloheptylbut-1-yl, 4-cycloheptylbut-1-yl, 1-cycloheptylbut-2-yl,
2-cycloheptylbut-2-yl, 3-cycloheptylbut-2-yl, 4-cycloheptylbut-2-yl,
1-(cycloheptylmethyl)eth-1-yl, 1-(cycloheptylmethyl)-1-(methyl)eth-1-yl,
1-(cycloheptylmethyl)prop-1-yl, cyclooctylmethyl, 1-cyclooctylethyl,
2-cyclooctylethyl, 1-cyclooctylprop-1-yl, 2-cyclooctylprop-1-yl,
3-cyclooctylprop-1-yl, 1-cyclooctylbut-1-yl, 2-cyclooctylbut-1-yl,
3-cyclooctylbut-1-yl, 4-cyclooctylbut-1-yl, 1-cyclooctylbut-2-yl,
2-cyclooctylbut-2-yl, 3-cyclooctylbut-2-yl, 4-cyclooctylbut-2-yl,
1-(cyclooctylmethyl)eth-1-yl, 1-(cyclooctylmethyl)-1-(methyl)eth-1-yl or
1-(cyclooctylmethyl)prop-1-yl, preferably cyclopropylmethyl, cyclobutylmethyl,
cyclopentylmethyl or cyclohexylmethyl.
[0053] C.sub.5-C.sub.10-cycloalkenyl: a mono- or bicyclic hydrocarbon radical
having 5 to 10 carbon atoms, in particular 5 to 8 carbon atoms and especially 5
to 6 carbon atoms and which contains a C.dbd.C double bond, for example
cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl,
cyclohexen-4-yl, cyclohepten-1-yl, cyclohepten-3-yl, cyclohepten-4-yl,
cycloocten-1-yl, cycloocten-3-yl, cycloocten-4-yl, cycloocten-5-yl,
bicyclo[2.2.1]hept-2-en-1-yl, bicyclo[2.2.1]hept-2-en-2-- yl,
bicyclo[2.2.1]hept-2-en-5-yl, bicyclo[2.2.1]hept-2-en-7-yl,
bicyclo[2.2.2]oct-2-en-1-yl, bicyclo[2.2.2]oct-2-en-2-yl,
bicyclo[2.2.2]oct-2-en-5-yl, bicyclo[2.2.2]oct-2-en-7-yl; [0054] unsubstituted
or substituted phenyl: a phenyl group which is unsubstituted or carries 1, 2, 3
or 4 substituents, where the substituents are selected from the group consisting
of halogen, nitro, cyano, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, COOR.sup.5,
NR.sup.6R.sup.7, C(O)NR.sup.8R.sup.9; [0055] 3- to 7-membered heterocyclyl: a
heterocyclic radical which has 3, 4, 5, 6 or 7 ring members, where 1, 2 or 3 of
the ring members are heteroatoms selected from the group consisting of oxygen,
nitrogen, sulfur, a group SO.sub.2 and a group NR.sup.10. Moreover, the
heterocycle may optionally contain 1, 2 or 3 carbonyl groups and/or thiocarbonyl
groups as ring members. The heterocycle may furthermore contain a ring-fused
unsubstituted or substituted phenyl ring. The heterocycle may be aromatic (heteroaryl)
or partially or fully saturated. [0056] Examples of saturated heterocycles are:
oxiran-1-yl, aziridin-1-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl,
thietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl,
tetrahydrofuran-3-yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl,
pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1,3-dioxolan-2-yl,
1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl,
1,3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl, 1,3-oxazolidin-3-yl,
1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl,
1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl,
1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, pyrrolidin-1-yl, pyrrolidin-2-yl,
pyrrolidin-5-yl, tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl,
tetrahydropyrazol-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl,
tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,
tetrahydropyran-4-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl,
piperidin-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl,
1,4-dioxan-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl,
1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, morpholin-2-yl,
morpholin-3-yl, morpholin-4-yl, hexahydropyridazin-1-yl,
hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl- ,
hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl,
piperazin-1-yl, piperazin-2-yl, piperazin-3-yl, hexahydro-1,3,5-triazin-1-yl,
hexahydro-1,3,5-triazin-2-yl, oxepan-2-yl, oxepan-3-yl, oxepan-4-yl,
thiepan-2-yl, thiepan-3-yl, thiepan-4-yl, 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl,
1,3-dioxepan-5-yl, 1,3-dioxepan-6-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-4-yl,
1,3-dithiepan-5-yl, 1,3-dithiepan-6-yl, 1,4-dioxepan-2-yl, 1,4-dioxepan-7-yl,
hexahydroazepin-1-yl, hexahydroazepin-2-yl, hexahydroazepin-3-yl,
hexahydroazepin-4-yl, hexahydro-1,3-diazepin-1-yl, hexahydro-1,3-diazepin-2-yl,
hexahydro-1,3-diazepin-4-yl, hexahydro-1,4-diazepin-1-yl and
hexahydro-1,4-diazepin-2-yl; [0057] Examples of unsaturated heterocycles are:
[0058] dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl,
1,3-oxazolin-2-yl; [0059] Examples of aromatic heterocyclyl are the 5- and
6-membered aromatic, heterocyclic radicals, for example furyl, such as 2-furyl
and 3-furyl, thienyl, such as 2-thienyl and 3-thienyl, pyrrolyl, such as
2-pyrrolyl and 3-pyrrolyl, isoxazolyl, such as 3-isoxazolyl, 4-isoxazolyl and
5-isoxazolyl, isothiazolyl, such as 3-isothiazolyl, 4-isothiazolyl and
5-isothiazolyl, pyrazolyl, such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl,
oxazolyl, such as 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl, such as
2-thiazolyl, 4-thiazolyl and 5-thiazolyl, imidazolyl, such as 2-imidazolyl and
4-imidazolyl, oxadiazolyl, such as 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl
and 1,3,4-oxadiazol-2-yl, thiadiazolyl, such as 1,2,4-thiadiazol-3-yl,
1,2,4-thiadiazol-5-yl and 1,3,4-thiadiazol-2-yl, triazolyl, such as
1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl, pyridinyl, such
as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl, such as 3-pyridazinyl
and 4-pyridazinyl, pyrimidinyl, such as 2-pyrimidinyl, 4-pyrimidinyl and
5-pyrimidinyl, furthermore 2-pyrazinyl, 1,3,5-triazin-2-yl and
1,2,4-triazin-3-yl, in particular pyridyl, pyrimidyl, furanyl and thienyl.
[0060] If the radicals R.sup.2 and R.sup.3 together with the nitrogen atom to
which they are attached form a saturated heterocycle, n is preferably 0. In this
case, the saturated heterocycle is selected, for example, from the group
consisting of 1,3-oxazolidin-3-yl, 1,2-oxazolidin-2-yl, pyrrolidin-1-yl,
pyrrolidin-2-on-1-yl, tetrahydropyrazol-1-yl, 2-methyltetrahydropyrazol-1-yl,
piperidin-1-yl, piperidin-2-on-1-yl, morpholin-4-yl, hexahydropyrimidin-1-yl,
piperazin-1-yl, 4-methylpiperazin-1-yl, hexahydro-1,3,5-triazin-1-yl,
3,5-dimethyltriazin-1-yl, hexahydroazepin-1-yl, hexahydroazepin-2-on-1-yl- ,
hexahydro-1,3-diazepin-1-yl, hexahydro-1,4-diazepin-1-yl, in particular from the
group consisting of pyrrolidin-1-yl, piperidin-1-yl and morpholin-4-yl.
|
|