Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-06-01
2003-03-25
O'Sullivan, Peter (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S274000, C514S347000, C514S367000, C514S375000, C514S427000, C514S438000, C514S471000, C514S600000, C514S604000, C514S605000, C514S607000, C544S408000, C546S294000, C546S295000, C548S217000, C548S180000, C548S542000, C548S561000, C549S077000, C549S496000, C564S084000, C564S085000, C564S086000, C564S087000, C564S088000, C564S089000, C564S090000, C564S091000, C564S097000, C564S099000
Reexamination Certificate
active
06538016
ABSTRACT:
The present invention relates to novel &agr;-sulfin- and &agr;-sulfonamino acid amides of formula I below. It relates to the preparation of those substances and to agrochemical compositions comprising at least one of those compounds as active ingredient. The invention relates also to the preparation of the said compositions and to the use of the compounds or of the compositions in controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.
The invention relates to &agr;-sulfin- and &agr;-sulfonamino acid amides of the general formula I
including the optical isomers thereof and mixtures of such isomers,
wherein
n is a number zero or one;
R
1
is C
1
-C
12
alkyl, C
1
-C
12
alkyl substituted with C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfonyl, C
3
-C
8
cycloalkyl, cyano, C
1
-C
6
alkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl or C
3
-C
6
alkynyloxycarbonyl; C
3
-C
8
cycloalkyl; C
2
-C
12
alkenyl; C
2
-C
12
alkynyl; C
1
-C
12
haloalkyl; or a group NR
12
R
13
wherein R
12
and R
13
are each independently of the other hydrogen or C
1
-C
6
-alkyl, or together are tetra- or penta-methylene;
R
2
and R
3
are each independently hydrogen; C
1
-C
8
alkyl; C
1
-C
8
alkyl substituted with hydroxy, mercapto, C
1
-C
4
alkoxy or C
1
-C
4
alkylthio; C
3
-C
8
alkenyl; C
3
-C
8
alkynyl; C
3
-C
8
cycloalkyl; C
3
-C
8
cycloalkyl-C
1
-C
4
alkyl; or the two groups R
2
and R
3
together with the carbon atom to which they are bonded form a three- to eight-membered hydrocarbon ring;
R
4
, R
5
, R
6
and R
7
are each independently hydrogen or C
1
-C
4
alkyl;
R
8
is C
1
-C
6
alkyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl;
R
9
and R
10
are each independently hydrogen or C
1
-C
4
alkyl; and
R
11
is either
in wherein
R
14
, R
15
, R
16
and R
17
are each independently hydrogen or C
1
-C
4
alkyl,
X is oxygen, sulfur or —NR
18
—, wherein R
18
is hydrogen or C
1
-C
4
alkyl, and
A is optionally substituted mono- or polycylic aryl or heteroaryl.
In the above definition aryl includes aromatic hydrocarbon rings like phenyl, naphthyl, anthracenyl, phenanthrenyl, with phenyl being preferred.
Heteroaryl stands for aromatic ring systems comprising mono-, bi- or tricyclic systems wherein at least one oxygen, nitrogen or sulfur atom is present as a ring member. Examples are furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, indazolyl, benzotriazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl and naphthyridinyl.
The above aryl and heteroaryl groups may carry one or more identical or different substituents. Normally not more than three substituents are present at the same time. Examples of substituents of aryl or heteroaryl groups are: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenyl-alkyl, it being possible in turn for all of the preceding groups to carry one or more identical or different halogen atoms; alkoxy; alkenyloxy; alkynyloxy; alkoxyalkyl; haloalkoxy, alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxy; alkoxycarbonyl; alkenyloxycarbonyl; alkynyloxycarbonyl.
In the above definitions “halogen” includes fluorine, chlorine, bromine and iodine.
The alkyl, alkenyl and alkynyl radicals may be straight-chain or branched. This applies also to the alkyl, alkenyl or alkynyl parts of other alkyl-, alkenyl- or alkynyl-containing groups.
Depending upon the number of carbon atoms mentioned, alkyl on its own or as part of another substituent is to be understood as being, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and the isomers thereof, for example isopropyl, isobutyl, tert-butyl or sec-butyl, isopentyl or tert-pentyl.
Cycloalkyl is, depending upon the number of carbon atoms mentioned, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
Depending upon the number of carbon atoms mentioned, alkenyl as a group or as a structural element of other groups is to be understood as being, for example, ethenyl, allyl, 1-propenyl, buten-2-yl, buten-3-yl, penten-1-yl, penten-3-yl, hexen-1-yl, 4-methyl-3-pentenyl or 4-methyl-3-hexenyl.
Alkynyl as a group or as a structural element of other groups is, for example, ethynyl, propyn-1-yl, propyn-2-yl, butyn-1-yl, butyn-2-yl, 1-methyl-2-butynyl, hexyn-1-yl, 1-ethyl-2-butynyl or octyn-1-yl.
A haloalkyl group may contain one or more (identical or different) halogen atoms, and for example may stand for CHCl
2
, CH
2
F, CCl
3
, CH
2
Cl, CHF
2
, CF
3
, CH
2
CH
2
Br, C
2
C
5
, CH
2
Br, CHClBr, CF
3
CH
2
, etc.
Where R
2
and R
3
together with the carbon atom to which they are attached form a hydrocarbon ring the ring corresponds to cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane or cyclooctane
The presence of at least one asymmetric carbon atom and/or at least one asymmetric oxidized sulfur atom in the compounds of formula I means that the compounds may occur in optically isomeric forms. As a result of the presence of a possible aliphatic C═C double bond, geometric isomerism may also occur. Formula I is intended to include all those possible isomeric forms and mixtures thereof.
Preferred subgroups of compounds of formula I are those wherein
n is one; or
R
1
is C
1
-C
12
alkyl, C
1
-C
12
alkyl substituted with C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, or C
1
-C
4
alkylsulfonyl; C
2
-C
12
alkenyl; C
2
-C
12
alkynyl; C
1
-C
12
haloalkyl; or a group NR
12
R
13
wherein R
12
and R
13
are each independently of the other hydrogen or C
1
-C
6
-alkyl, or together are tetra- or penta-methylene; or
R
1
is C
1
-C
12
alkyl, C
2
-C
12
alkenyl; C
1
-C
12
haloalkyl; or a group NR
12
R
13
wherein R
12
and R
13
are each independently of the other hydrogen or C
1
-C
6
-alkyl; or
R
1
is C
1
-C
4
alkyl, C
2
-C
4
alkenyl; C
1
-C
4
haloalkyl; or C
1
-C
2
-dialkylamino; or
R
1
is C
1
-C
4
alkyl, vinyl; C
1
-C
4
haloalkyl; or dimethylamino; or
R
2
is hydrogen and R
3
is C
1
-C
8
alkyl; C
1
-C
8
alkyl substituted with hydroxy, mercapto, C
1
-C
4
alkoxy or C
1
-C
4
alkylthio; C
3
-C
8
alkenyl; C
3
-C
8
alkynyl; C
3
-C
8
cycloalkyl; C
3
-C
8
cycloalkyl-C
1
-C
4
alkyl; or
R
2
is hydrogen and R
3
is C
1
-C
4
alkyl; C
3
-C
4
alkenyl or cyclopropyl; or
R
2
is hydrogen and R
3
is C
3
-C
4
alkyl; allyl or cyclopropyl; or
R
2
is hydrogen and R
3
is isopropyl; or
R
4
is hydrogen or C
1
-C
4
alkyl and R
5
, R
6
and R
7
are each hydrogen; or
R
4
is hydrogen, methyl or ethyl and R
5
, R
6
and R
7
are each hydrogen; or
R
4
is hydrogen or methyl and R
5
, R
6
and R
7
are each hydrogen; or
R
4
, R
5
, R
6
and R
7
are each hydrogen; or
R
8
is C
1
-C
6
alkyl; or
R
8
is methyl or ethyl; or
R
8
is methyl; or
R
9
, R
10
, R
14
, R
15
, R
16
, R
17
are each independently hydrogen or methyl; or
R
9
, R
10
, R
14
, R
15
, R
16
, R
17
are each hydrogen; or
X is oxygen, sulfur or —NR
8
—, wherein R
18
is hydrogen or methyl; or
X is oxygen, sulfur or —NH—; or
X is oxygen; or
A is optionally substituted heteroaryl consisting of one or two five to six membered rings containing one to four identical or different heteroatoms selected from oxygen, nitrogen and sulfur; or
A is phenyl, naphthyl, furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, isoxazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, benzthiazolyl, benzoxazolyl or quinolyl, each optionally substituted by 1 to 3 substituents selected from C
1
-C
8
-alkyl, C
2
-C
8
-alkenyl, C
2
-C
8
-alkynyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
4
-alkyl, phenyl, phenyl-C
1
-C
4
-alkyl wherein the hydrogens of all the preceding substituents may be in turn optionally substituted by one or several same or different haloge
Jeanguenat André
Lamberth Clemens
Zeller Martin
Allen Rose M.
O'Sullivan Peter
Syngenta Participations (AG)
Teoli, Jr. William A.
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