N-sulphonyl and N-sulphinyl amino acid derivatives as...

Details N-sulphonyl and N-sulphinyl amino acid derivatives as... N-sulphonyl and N-sulphinyl amino acid derivatives as...

1998-04-16

2001-02-27

Wilson, James O. (Department: 1623)

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

Organic compounds

Amino nitrogen containing

C564S080000, C564S099000, C564S100000, C564S189000, C564S191000, C564S196000, C548S542000, C560S009000, C560S013000

Reexamination Certificate

active

06194611

ABSTRACT:

The present invention relates to novel a-amino acid amides of formula I below. It relates to the preparation of those substances and to agrochemical compositions that comprise at least one of those compounds as active ingredient The invention also relates to the preparation of the said compositions and to the use of the active ingredients or the compositions in the control or prevention of plant infestation 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 the number zero or one;
R
1
is C
1
-C
12
alkyl that is unsubstituted or may be substituted by C
4
alkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfonyl, C
3
-Cgcycloalkyl, cyano, C
1
-C
6
alkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl or by 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 or C
1
-C
6
alkyl, or together are tetramethylene or pentamethylene;
R
2
and R
3
are each independently of the other hydrogen; C
1
-C
8
alkyl; C
1
-C
8
alkyl substituted by hydroxy, C
1
-C
4
alkoxy, mercapto or by C
1
-C
4
alkylthio; C
3
-C
8
alkenyl; C
3
-C
8
-alkynyl or 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 carbocyclic ring;
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 the 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 mono- or poly-substituted 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
alkynyloxycarbonyl, 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.
A preferred group is formed by compounds of formula I
wherein the substituents are defined as follows:
n is the 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
alkylsulfonyl, C
3
-C
8
cycloalkyl, cyano, C
1
-C
6
alkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl or by 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
1
and R
12
are each independently of the other hydrogen or C
1
-C
6
alkyl, or together are tetramethylene or pentamethylene;
R
2
and R
3
are each independently of the other hydrogen; C
1
-C
8
alkyl; C
1
-C
8
alkyl substituted by hydroxy, C
1
-C
4
alkoxy, mercapto or by C
1
-C
4
alkylthio; C
3
-C
8
alkenyl; C
3
-C
8
-alkynyl or 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 carbocyclic ring;
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 the 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 1A).
An important group is formed by compounds of formula I wherein
n is the 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 or by 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 or C
1
-C
6
-alkyl, or together are tetramethylene or pentamethylene;
R
2
is hydrogen; and
R
3
is C
1
-C
8
alkyl; C
1
-C
8
alkyl substituted by hydroxy, C
1
-C
4
alkoxy, mercapto or by C
1
-C
4
-alkylthio; C
3
-C
8
alkenyl; C
3
-C
8
alkynyl or C
3
-C
8
cycloalkyl-C
1
-C
4
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
-Cgcycloalkyl; 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 the 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
allyl, 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 the 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 or by 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 tetramethylene or pentamethylene;
R
2
is hydrogen; and
R
3
is C
1
-C
8
alkyl; C
1
-C
8
alkyl substituted by hydroxy, C
1
-C
4
alkoxy, mercapto or by C
1
-C
4
-alkylthio; C
3
-C
8
alkenyl; C
3
-C
8
alkynyl or C
3
-C
8
cycloalkyl-C
1
-C
4
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 the number zero or one; and
R
13
, R
14
, R
15
and R
16
are identical or different and are each independently of the oth

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