Fungicidal phenylamidine derivatives

Details Fungicidal phenylamidine derivatives Fungicidal phenylamidine derivatives

2001-08-06

2003-12-16

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C564S244000, C564S245000, C564S247000

Reexamination Certificate

active

06664295

ABSTRACT:

This invention relates to new fungicidal phenylamidine derivatives, their process of preparation and the fungicidal compositions containing them.
WO 95/22532 relates to substituted phenyltriazolinones claimed as herbicides and discloses inter alia a compound of formula A for which there is no characterising data therein.
The abstract, composition claim and use claim refer only to the use of such compounds as herbicides and indeed the description supports the invention only with herbicidal activity data. There is a sentence in the specification that states that certain compounds show fungicidal activity, although no fungicidal activity data are provided. No indication is given as to which compounds are fungicidal and there is no suggestion that compound A could be fungicidal.
We have now found that certain phenylamidines have fungicidal activity. Therefore, the invention provides the use of a compound of general formula (I) and salts thereof as fungicides:
wherein
R
1
is chosen from among alkyl, alkenyl, alkynyl, acyl, carbocyclyl, heterocyclyl, each of which may be substituted, cyano and hydrogen;
R
2
and R
3
, which may be the same or different, are any group defined for R
1
; cyano; acyl; —OR
a
, —NR
a
R
b
or —SR
a
, where R
a
and R
b
, which may be the same or different, are chosen from alkyl, alkenyl, alkynyl, acyl, carbocyclyl, heterocyclyl, each of which may be substituted, and cyano; or
R
2
and R
3
, or R
2
and R
1
, together with their interconnecting atoms may form a ring, which may be substituted;
R
4
is chosen from among alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, each of which may be substituted; hydroxy; mercapto; azido; nitro; halogen; cyano; acyl; optionally substituted amino; cyanato; thiocyanato; —SF
5
; —OR
a
; —SR
a
and —Si(R
a
)
3
, where R
a
is alkyl, alkenyl, alkynyl, carbocyclyl or heterocyclyl, each of which may be substituted;
m is 0 to 3;
when present R
5
, which may be the same or different to any other R
5
, is any group defined for R
4
;
R
6
is optionally substituted carbo- or hetero-cyclyl; and
A is a direct bond, —O—, —S(O)
n
—, —NR
9
—, —CR
7
═CR
7
—, —C≡C—, —A
1
—, —A
1
—A
1
—, —O—(A
1
)
k
—O—, —O—(A
1
)
k
—, —A
3
—, —A
4
—, —A
1
O—, —A
1
S(O)
n
—, —A
2
—, —OA
2
—, —NR
9
A
2
—, —OA
2
—A
1
—, —OA
2
—C(R
7
)═C(R
8
)—, —S(O)
n
A
1
—, —A
1
—A
4
—, —A
1
—A
4
—C(R
8
)═N—N═CR
8
—, —A
1
—A
4
—C(R
8
)═N—X
2
—X
3
—, —A
1
—A
4
—A
3
—, —A
1
—A
4
—N(R
9
)—, —A
1
—A
4
—X—CH
2
—, A
1
—A
4
—A
1
—, —A
1
—A
4
—CH
2
X—, —A
1
—A
4
—C(R
8
)═N—X
2
—X
3
—X
1
—, —A
1
—X—C(R
8
)═N—, —A
1
—X—C(R
8
)═N—N═CR
8
—, —A
1
—X—C(R
8
)═N—N(R
9
)—, —A
1
—X—A
2
—X
1
—, —A
1
—O—A
3
—, —A
1
—O—C(R
7
)═C(R
8
)—, —A
1
—O—N(R
9
)—A
2
—N(R
9
)—, —A
1
—O—N(R
9
)—A
2
—, —A
1
—N(R
9
)—A
2
—N(R
9
)—, —A
1
—N(R
9
)—A
2
—, —A
1
—N(R
9
)—N═C(R
8
)—, —A
3
—A
1
—, —A
4
—A
3
—, —A
2
—NR
9
—, —A
1
—A
2
—X
1
—, —A
1
—A
1
—A
2
—X
1
—, —O—A
2
—N(R
9
)—A
2
—, —CR
7
═CR
7
—A
2
—X
1
—, —C≡C—A
2
—X
1
—, —N═C(R
8
)—A
2
—X
1
—, —C(R
8
)═N—N═C(R
8
)—, —C(R
8
)═N—N(R
9
)—, —(CH
2
)
2
—O—N═C(R
8
)—ou—X—A
2
—N(R
9
)—
where:
n is 0, 1 or 2,
k is 1 to 9,
A
1
is —CHR
7
—,
A
2
is —C(═X)—,
A
3
is —C(R
8
)═N—O—,
A
4
is —O—N═C(R
8
)—,
X is O or S,
X
1
is O, S, NR
9
or a direct bond,
X
2
is O, NR
9
or a direct bond,
X
3
is hydrogen, —C(═O)—, —SO
2
— or a direct bond,
R
7
, which may be the same or different to any other R
7
, is alkyl, alkenyl, alkynyl, cyano, acyl, hydroxy, alkoxy, haloalkoxy, alkylthio, cycloalkyl or phenyl, each of which may be substituted; or is hydrogen or halogen;
R
8
, which may be the same or different to any other R
8
, is alkyl, alkenyl, alkynyl, alkoxy, alkylthio, carbo- or hetero-cyclyl, each of which may be substituted; or is hydrogen;
R
9
, which may be the same or different to any other R
9
, is optionally substituted alkyl, optionally substituted carbo- or hetero-cyclyl, hydrogen or acyl; or two R
9
groups on A, together with the connecting atoms, form a 5 to 7 membered ring;
where the moiety depicted on the right side of linkage A is attached to R
6
;
or —A—R
6
and R
5
together with benzene ring M form an optionally substituted fused ring system.
Preferably R
1
is alkyl, alkenyl, alkynyl or acyl, each of which may be substituted by alkoxy, haloalkoxy, alkylthio, halogen or optionally substituted phenyl (preferably phenyl optionally substituted by alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio, each containing 1 to 5 carbon atoms, or halogen), or is cyano or hydrogen. R
1
is especially C
1
-C
10
alkyl (e.g. methyl) or hydrogen.
Preferably R
2
and R
3
, which may be the same or different, are alkyl, alkenyl or alkynyl, each of which may be substituted by alkoxy, haloalkoxy, alkylthio, halogen or optionally substituted phenyl (preferably phenyl, optionally substituted by alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio, each containing 1 to 5 carbon atoms, or by halogen), or is hydrogen or alkycarbonyl. R
2
and R
3
, which may be the same or different, are especially C
1
-C
10
alkyl (e.g. methyl or ethyl) or hydrogen.
Preferably R
4
is alkyl, alkenyl, or alkynyl, each of which may be substituted by alkoxy, haloalkoxy, alkylthio, halogen or optionally substituted phenyl (preferably phenyl optionally substituted by alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio, each containing 1 to 5 carbon atoms, or halogen); or is hydroxy; halogen; cyano; acyl (preferably —C(═O)R
c
, —C(═S)R
c
or —S(O)
p
R
c
, where R
c
is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, amino, monoalkylamino, dialkylamino or phenyl optionally substituted by alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio; phenyloxy, phenylthio, carbocyclyl, heterocyclyl); alkoxy; haloalkoxy; or alkylthio. R
4
is especially C
1
-C
10
alkyl (e.g. methyl or ethyl) or halogen.
Preferably m is 0 or 1, especially 1.
When present, R
5
is preferably a group defined for preferred R
4
above. R
5
is especially C
1
-C
10
alkyl or halogen.
When present, the group R
5
is preferably attached at the 5 position of ring M.
Preferably A is a direct bond, —O—, —S(O)
n
A
1
—, —O(A
1
)
k
—, —S(O)
n
—, —NR
9
A
2
—, —A
2
—, —OA
2
—, —OA
2
—A
1
—, —NR
9
— or —O(A
1
)
k
O—. Particularly A is a direct bond, —O—, —S—, —NR
9
—, —CHR
7
— or —O—CHR
7
—. Especially A is a direct bond or —O—.
When present, R
9
is alkyl, alkenyl, or alkynyl, each of which may be substituted by alkoxy, haloalkoxy, alkylthio, halogen or optionally substituted phenyl (preferably phenyl optionally substituted by alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio, each containing 1 to 5 carbon atoms, or halogen); or is hydrogen (R
9
is especially C
1
-C
10
alkyl or hydrogen).
When present, R
7
is alkyl, alkenyl, or alkynyl, each of which may be substituted by alkoxy, haloalkoxy, alkylthio, halogen or optionally substituted phenyl (preferably phenyl optionally substituted by alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio, each containing 1 to 5 carbon atoms, or by halogen); or is hydroxy; halogen; cyano; acyl; alkoxy; haloalkoxy; alkylthio; or hydrogen (R
7
is especially C
1
-C
10
alkyl or hydrogen).
Preferably A is attached to the 4 position of benzene ring M.
Preferably R
6
is optionally substituted phenyl or optionally substituted aromatic heterocyclyl [preferably thiazolyl, isothiazolyl, thiadiazolyl (particularly 1,2,4-thiadiazolyl), pyridyl or pyrimidinyl].
When substituted, R
6
may be substituted by one or more substituents, which may be the same or different, and may be selected from the preferred list: alkyl, alkenyl, alkynyl, carbo- or heterocyclyl, each of which may be substituted; hydroxy; mercapto; azido; nitro; halogen; cyano; acyl; optionally substituted amino; cyanato; thiocyanato; —SF
5
; —OR
a
; —SR
a
and —Si(R
a
)
3
, where R
a
is alkyl, alkenyl, alkynyl, carbocyclyl or heterocyclyl, each of which may be substituted.
A preferred list of substituents on R
6
is: hydroxy; halogen; cyano; acyl (preferably —C(═O)R
c
, —C(═S)R
c
or —S(O)
p
R
c
, where R
c
is

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