Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-11-26
2003-12-30
Gerstl, Robert (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S373000, C548S209000, C548S212000, C548S213000, C548S214000
Reexamination Certificate
active
06670385
ABSTRACT:
The present invention relates to novel aryl-substituted S(O)
m
cycles (&agr;-phenyl-&bgr;-keto sulphones), to a plurality of processes for their preparation and to their use in agriculture, for example as crop protection agents (for example as fungicides, herbicides and insecticides).
4-Amino-5-phenyl-3-ethyl-2-methyl-2,3-dihydroisothiazole 1,1-dioxide (J. L. Marco et al., Tetrahedron Letters 39, 4123 (1998)), 4-amino-5-phenyl-3,3-dimethyl-2-benzyl-2,3-dihydroisothiazole 1,1-dioxide and 4-amino-5-phenyl-3,3-dimethyl-2-(3-chloro-benzyl)-2,3-dihydroisothiazole 1,1-dioxide (S. T. Ingate, et al., Tetrahedron 53, 17795 (1997)) are known from the literature. Also known are 2-methyl-5-phenyl-isothiazolidin-4-one 1,1-dioxide, 2,3-dimethyl-5-phenyl-isothiazolidin-4-one 1,1-dioxide and 5-phenyl-2,3,3-trimethyl-isothiazolidin-4-one 1,1-dioxide (H.-D. Stachel, G. Drasch, Archiv Pharm. 318, 304 (1985)). Use of these compounds as crop protection agents or pesticides has hitherto not been disclosed.
Furthermore known are 3-phenyl-1,2-oxathiolan-4-one 2,2-dioxide, 5-methyl-3-phenyl-1,2-oxathiolan-4-one 2,2-dioxide, 5,5-dimethyl-3-phenyl-1,2-oxathiolan-4-one 2,2-dioxide (H. D. Stachel, G. Drasch, Archiv Pharm. 318, 304 (1985)), 5-amino-5,5-dimethyl-3-phenyl-1,2-oxathiolane 2,2-dioxide and 4-amino-5-methyl-3-phenyl-5-phenylmethyl-1,2-oxathiolane 2,2-dioxide (S. T. Ingate et al., Tetrahedron 53, 17795 (1997)). Use of these compounds as crop protection agents or pesticides has hitherto not been disclosed.
2-Arylbenzo[b]thiophen-3(2H)-one 1,1-dioxides have been disclosed for use as anti-inflammatory agents and anticoagulants (J. G. Lombardino, E. H. Wiseman, J. Med. Chem., 13, 206 (1970)). Also known is 2-phenyl-3-keto-tetrahydrothiophene 1,1-dioxide (A. Abdel-Wahab et al., Phosphorus, Sulfur and Silicon, 59, 149 (1991)). Furthermore known are 2-phenylbenzo[b]thiophene-3-amine, 2-phenylbenzo[b]-thiophene-3-amine 1-oxide and 2-phenylbenzo[b]thiophene-3-amine 1,1-dioxide (J. R. Beck, J. Heterocyclic Chem. 15, 513 (1978)). Likewise, a use of these compounds as crop protection agents or pesticides has hitherto not been disclosed.
This invention, accordingly, provides aryl-substituted S(O)
m
cycles of the general formula (I)
in which
V, W, X, Y and Z independently of one another each represent hydrogen, halogen, nitro, cyano or a radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, S(O)
n
-alkyl, halogenoalkyl, halogenoalkoxy, in each case optionally substituted aryl, phenylalkyl, aryloxy, phenyl-alkyloxy or aryl-S(O)
n
—, where two adjacent radicals together with the carbon atoms to which they are attached form an optionally substituted ring which is optionally interrupted by one or more heteroatoms;
with the proviso that at least one radical of the substituents V, W, X, Y or Z has to be different from hydrogen,
n represents the numbers 0 to 2,
m represents the numbers 1 and 2,
F
1
and F
2
represent one of the groups
in which
A represents hydrogen, in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom, or represents in each case optionally halogen-, alkyl-, halogenoalkyl-, alkoxy-, halogenoalkoxy-, cyano- or nitro-substituted aryl, arylalkyl or hetaryl,
B represents hydrogen, alkyl or alkoxyalkyl, or
A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle which optionally contains at least one heteroatom,
D represents hydrogen or an optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkyl in which optionally one or more ring members are replaced by heteroatoms, represents optionally substituted arylalkyl, aryl, hetarylalkyl, hetaryl or CO—R
11
, or
A and D together with the atoms to which they are attached represent a saturated or unsaturated cycle which is unsubstituted or substituted in the A,D-moiety and optionally contains at least one (in the case of —F
1
—F
2
=(4) further) heteroatom, or
A and Q
1
together represent alkanediyl or alkenediyl, each of which is optionally substituted by in each case optionally substituted alkyl, hydroxyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, or represent an optionally substituted alkanedienediyl, with the proviso that B and Q
2
together with the carbon atoms to which they are attached represent a double bond and at least one of the substituents W or X does not represent hydrogen,
Q
1
represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkyl in which optionally one or more ring members are replaced by heteroatoms, or represents optionally substituted phenyl,
Q
2
represents hydrogen or alkyl,
G represents hydroxyl (a) or represents one of the groups
in which
E represents a metal ion or an ammonium ion,
L represents oxygen or sulphur,
M represents oxygen or sulphur,
R
1
represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl in which one or more methylene groups may be replaced by heteroatoms, or represents in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R
2
represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R
3
, R
4
and R
5
independently of one another each represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio and represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio and
R
6
and R
7
independently of one another each represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent optionally substituted phenyl, represent optionally substituted benzyl, or together with the N atom to which they are attached represent an optionally substituted ring which is optionally interrupted by oxygen or sulphur,
R
8
represents in each case optionally halogen-substituted alkyl, alkoxyalkyl, alkenyl, alkenyloxyalkyl, alkinyl, alkinyloxyalkyl, alkylcarbonylalkyl, alkoxycarbonylalkyl or represent optionally substituted cycloalkyl or represent optionally substituted arylalkyl, arylcarbonylalkyl or phenoxyalkyl,
R
9
and R
10
independently of one another each represent hydrogen, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, represent cycloalkyl which is optionally interrupted by heteroatoms, represent in each case optionally substituted phenyl, phenylalkyl, phenoxyalkyl, hetaryl or hetarylalkyl, or
R
9
and R
10
together with the nitrogen to which they are attached form a 3- to 9-membered ring which is optionally substituted and optionally interrupted by further heteroatoms, or
R
10
represents the group CO—R
11
, where
R
11
represents hydrogen, optionally halogen-substituted alkyl, alkenyl, alkoxy, optionally substituted cycloalkyl which may optionally be interrupted by heteroatoms, or represents optionally substituted aryl, arylalkyl, arylalkyloxy or phenoxy, possible substituents being halogen, nitro, cyano, alkyl, alkoxy, halogenoalkyl and halogenoalkoxy.
Depending inter alia on the nature of the substituents, the compounds of the formula (I) can be present as geometric and/or optical isomers or isomer mixtures of different composition which, if appropriate, can be separated in a customary manner. The present invention provides both the pure isomers and the isomer mixtures, their preparation and use and the compositions comprising them. However, hereinbelow, for the sake of simplicity, compounds of the formula (I) are always referred to, although this may mean both the pure
Andersch Wolfram
Drewes Mark Wilhelm
Erdelen Christoph
Feucht Dieter
Fischer Reiner
Bayer Aktiengesellschaft
Gerstl Robert
Gil Joseph C.
Henderson Richard E. L.
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