N-sulphonyl and N-sulphinyl amino acid amides as microbicides

Details N-sulphonyl and N-sulphinyl amino acid amides as microbicides N-sulphonyl and N-sulphinyl amino acid amides as microbicides

1999-08-24

2001-02-27

O'Sullivan, Peter (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

C514S521000, C514S531000, C514S542000, C514S600000, C514S605000, C514S608000, C558S404000, C560S013000, C564S079000, C564S099000, C564S101000, C564S102000

Reexamination Certificate

active

06194463

ABSTRACT:

The present invention relates to novel &agr;-amino 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 the compositions in controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.
The compounds according to the invention correspond to the general formula I
wherein the substituents are defined as follows:
n is a number zero or one;
R
1
is C
1
-C
12
alkyl that is unsubstituted or may be substituted by C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsufonyl, C
3
-C
8
cycloalkyl, cyano, C
1
-C
6
alkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl, 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
11
R
12
; wherein R
11
and R
12
are each independently of the other hydrogen, C
1
-C
6
alkyl or together are tetra- or penta-methylene;
R
2
is hydrogen, C
1
-C
8
alkyl;
R
3
is C
3
-C
8
cycloalkyl that is unsubstituted or may be substituted by C
1
-C
6
alkyl, hydroxy, C
1
-C
4
alkoxy, mercapto or by C
1
-C
4
alkylthio;
R
4
, R
5
, R
6
and R
7
are identical or different and are each independently of the others 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
is C
3
-C
8
cycloalkyl; a C
1
-C
6
alkyl-, C
3
-C
6
alkenyl- or C
3
-C
6
alkynyl-group each of which is substituted by one or more halogen atoms; or a group
wherein
p and q are identical or different and are each independently of the other a number zero or one; and
R
13
, R
14
, R
15
and R
16
are identical or different and are each independently of the others hydrogen or C
1
-C
4
alkyl;
X is hydrogen, in which case p and q must have the value zero; phenyl, unsubstituted or mono- or poly-substituted, for example, by halogen, nitro, cyano, carboxy, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy, C
3
-C
7
cycloalkyl, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio, C
1
-C
6
alkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl, C
3
-C
6
alknyloxycarbonyl, C
1
-C
6
alkyl or by C
1
-C
6
alkoxy; cyano; —COOR
17
; —COR
18
or a group
wherein
R
17
and R
21
are each independently of the other hydrogen, C
1
-C
6
alkyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl, and
R
18
is hydrogen; C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl or phenyl, unsubstituted or substituted by halogen, nitro, cyano, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy, and
R
19
and R
20
are identical or different and are each independently of the other hydrogen or C
1
-C
4
alkyl.
An important group is formed by compounds of formula I wherein
n is a number one;
R
1
is C
1
-C
12
alkyl that is unsubstituted or may be substituted by C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfonyl; C
2
-C
12
alkenyl; C
2
-C
12
alkynyl; C
1
-C
12
haloalkyl or a group NR
11
, R
12
;
wherein R
11
and R
12
are each independently of the other hydrogen, C
1
-C
6
alkyl or together are tetra- or penta-methylene;
R
2
is hydrogen;
R
3
is C
3
-C
7
cycloalkyl that is unsubstituted or may be substituted by C
1
-C
6
alkyl;
R
4
, R
5
, R
6
and R
7
are identical or different and are each independently of the others 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
is C
3
-C
8
cycloalkyl; a C
1
-C
6
alkyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl group substituted by one or more halogen atoms; or a group
wherein
p and q are identical or different and are each independently of the other a number zero or one; and
R
13
, R
14
, R
15
and R
16
are identical or different and are each independently of the others hydrogen or C
1
-C
4
alkyl; and
X is hydrogen, in which case p and q must have the value zero; phenyl, unsubstituted or substituted by halogen, nitro, cyano, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy; cyano; —COOR
17
; —COR
18
or a group
wherein
R
17
and R
21
, are each independently of the other hydrogen, C
1
-C
6
alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
alkynyl, and
R
18
is hydrogen; C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl or phenyl, unsubstituted or substituted by halogen, nitro, cyano, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy, and
R
19
and R
20
are identical or different and are each independently of the other hydrogen or C
1
-C
4
alkyl (sub-group A).
An important group is formed by compounds of formula I wherein n is a number one;
R
1
is C
1
-C
12
alkyl that is unsubstituted or may be substituted by C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfonyl; C
2
-C
12
alkenyl; C
2
-C
12
alkynyl; C
1
-C
12
haloalkyl or a group NR
11
R
12
;
wherein R
11
and R
12
are each independently of the other C
1
-C
6
alkyl or together are tetra- or penta-methylene;
R
2
is hydrogen; and
R
3
is C
3
-C
7
cycloalkyl that is unsubstituted or may be substituted by C
1
-C
6
alkyl;
R
4
, R
5
, R
6
and R
7
are identical or different and are each independently of the others hydrogen or C
1
-C
4
alkyl;
R
8
is C
1
-C
6
alkyl;
R
9
is C
3
-C
8
cycloalkyl; a C
1
-C
6
alkyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl group substituted by one or more halogen atoms; or a group
wherein
p and q are identical or different and are each independently of the other a number zero or one; and
R
13
, R
14
, R
15
and R
16
are identical or different and are each independently of the others hydrogen or C
1
-C
4
alkyl; and
X is hydrogen, in which case p and q must have the value zero; phenyl, unsubstituted or substituted by halogen, nitro, cyano, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy; cyano; —COOR
17
; —COR
18
or a group
wherein
R
17
and R
21
are each independently of the other hydrogen, C
1
-C
6
alkyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl, and
R
18
is hydrogen; C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl or phenyl, unsubstituted or substituted by halogen, nitro, cyano, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy, and
R
19
and R
20
are identical or different and are each independently of the other hydrogen or C
1
-C
4
alkyl (sub-group B).
Of special importance are compounds of formula I wherein
n is a number one;
R
1
is C
1
-C
12
alkyl; C
1
-C
12
haloalkyl or a group NR
11
R
12
; wherein R
11
and R
12
are C
1
-C
6
alkyl;
R
2
is hydrogen; and
R
3
is C
3
-C
7
cycloalkyl that is unsubstituted or may be substituted by C
1
-C
6
alkyl;
R
4
is hydrogen or C
1
-C
4
alkyl;
R
5
, R
6
and R
7
are hydrogen;
R
8
is C
1
-C
6
alkyl;
R
9
is C
3
-C
8
cycloalkyl; a C
1
-C
6
alkyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl group substituted by one or more halogen atoms; or a group
wherein
p and q are identical or different and are each independently of the other a number zero or one; and
R
13
, R
14
, R
15
and R
16
are identical or different and are each independently of the others hydrogen or C
1
-C
4
alkyl; and
X is hydrogen, in which case p and q must have the value zero; phenyl, unsubstituted or substituted by halogen, nitro, cyano, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy; cyano; —COOR
17
; —COR
18
or a group
wherein
R
17
and R
21
are each independently of the other hydrogen, C
1
-C
6
alkyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl, and
R
18
is hydrogen; C
1
-C
6
alkyl C
3
-C
6
alkenyl, C
3
-C
6
alkynyl or phenyl, unsubstituted or substituted by halogen, nitro, cyano, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy, and
R
19
and R
20
are identical or different and are each independently of the other hydrogen or C
1
-C
4
alkyl (sub-group Ba).
Another important group is formed by compounds of formula I wherein
n is a number one;
R
1
is C
1
-C
4
alkyl or dimethylamino;
R
2
is hydrogen; and
R
3
is C
3
-C
6
cycloalkyl that is unsubstituted or may be substituted by C
1
-C
4
alkyl;
R
4
is hydrogen or methyl;
R
5
, R
6
and R
7
are hydrogen;
R
8
is C
1
-C
2
alkyl;
R
9
is C
3
-C
8
cycloalkyl; a C
1
-C
6
alkyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl group substituted by one or more halogen atoms; or a group
wherein
p and q are identical or different and are each indepe

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