&agr;-sulfin-and &agr;-sulfonamino acid amides

Details &agr;-sulfin-and &agr;-sulfonamino acid amides &agr;-sulfin-and &agr;-sulfonamino acid amides

2001-06-01

2003-03-25

O'Sullivan, Peter (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C514S600000, C514S604000, C514S605000, C514S607000, C548S542000, C564S079000, C564S084000, C564S085000, C564S086000, C564S087000, C564S088000, C564S089000, C564S090000, C564S091000, C564S097000, C564S099000

Reexamination Certificate

active

06538159

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 (east 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
alkylsulfony C
3
-C
8
cycloalkyl, cyano, C
1
-C
6
alkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl or C
3
-C
6
alkenyloxycarbonyl; 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
, R
10
, R
14
, R
15
, R
16
and R
17
are each independently hydrogen or C
1
-C
4
alkyl;
A is optionally substituted phenyl.
The above definition the phenyl group of radical A may carry one or more identical or different substituents. Normally not more than three substituents are present at the same time. Examples of the phenyl group 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; alkenyloxycarbonyl.
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, vinyl, allyl, 1-propenyl, buten-2-yl, buten-3-yl, penten-1-yl, penten-3-yl, hexen-1-yl, 4-methyl-3-penten 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 stands for CHCl
2
, CH
2
F, CCl
3
, CH
2
Cl, CHF
2
, CF
3
, CH
2
CH
2
Br, C
2
Cl
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
A is phenyl, 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 halogens; C
1
-C
8
-alkoxy; C
3
-C
8
-alkenyloxy; C
3
-C
8
-alkynyloxy; C
1
-C
8
-alkoxy-C
1
-C
4
-alkyl; C
1
-C
8
halogenalkoxy; C
1
-C
8
-alkylthio; C
1
-C
8
-halogenalkylthio; C
1
-C
8
-alkylsulfonyl; formyl; C
2
-C
8
-alkanoyl; hydroxy; halogen; cyano; nitro; amino; C
1
-C
8
-alkylamino; C
1
-C
8
-dialkylamino; carboxy; C
1
-C
8
-alkoxycarbonyl; C
1
-C
8
-alkenyloxycarbonyl or C
1
-C
8
-alkenyloxycarbonyl; or
A is phenyl, optionally substituted by 1 to 3 substituents selected from C
1
-C
8
-alkyl, C
2
-C
8
-alkenyl wherein the hydrogens of all the preceding substituents may be in turn optionally substituted by one or several same or different halogens; C
1
-C
8
-alkoxy; C
1
-C
8
halogenalkoxy; C
1
-C
8
-alkylthio; C
1
-C
8
-halogenalkylthio; halogen; cyano; nitro or C
1
-C
8
-alkoxycarbonyl; or
A is phenyl, optionally substituted by 1 to 3 substituents selected from C
1
-C
8
-alkyl; C
1
-C
8
-haloalkyl; C
1
-C
8
-alkoxy; C
1
-C
8
halogenalkoxy; C
1
-C
8
-alkylthio; C
1
-C
8
-halogenalkylthio; halogen; cyano; nitro or C
1
-C
8
-alkoxycarbonyl.
Further preferred subgroups of the compounds of formula I are those wherein
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; and
R
2
is hydrogen and R
3
is C
1
-C
8
alkyl; C
1
-C
8
alkyl substituted

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