Fungicidal phenyl(thio)urea and phenyl(thio)carbamate...

Details Fungicidal phenyl(thio)urea and phenyl(thio)carbamate... Fungicidal phenyl(thio)urea and phenyl(thio)carbamate...

2001-08-06

2004-02-24

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

N-c doai

C514S478000, C514S586000, C514S587000, C514S596000, C514S598000, C558S234000, C558S236000, C560S024000, C560S027000, C560S029000, C562S027000, C562S443000, C562S444000, C564S028000, C564S048000, C564S052000

Reexamination Certificate

active

06696487

ABSTRACT:

The present invention relates to novel fungicidal phenyl(thio)urea and phenyl(thio)carbamate derivatives, to a process for preparing them and to fungicidal compositions containing them.
Patent application WO 95/22532 describes phenyltriazolinones with herbicidal activity. In particular, the compound of formula (A) is presented, for which no characteristics are given:
The abstract and the composition claims and use claims of the said patent application refer solely to the use of such compounds for herbicidal purposes; specifically, the description supports this description solely with herbicidal activity data. Mention is simply made in the said patent application of a possible fungicidal activity for certain compounds. However, no fungicidal activity data is produced. There are no indications regarding the nature of the compounds liable to have such fungicidal activity, and there is no disclosure as regards the fungicidal activity of compound (A).
The Applicant has now discovered that certain novel carbamates, thiocarbamates, ureas and thioureas, and also derivatives thereof, have fungicidal activity. Thus, the invention relates to the compounds of general formula (I) and also to salts thereof:
in which
W represents O or S;
Y represents a radical —NR
1
R
2
, —OR
3
or —SR
3
;
R
0
represents an alkyl, alkenyl, alkynyl, acyl, cyano, carbocyclyl or heterocyclyl radical, each of which may be substituted; or a hydrogen atom; or represents a single bond with Y;
R
1
and R
2
, which may be identical or different, represent any one of the groups defined for R
0
; or —NR
a
R
b
, —OR
a
, —SR
a
, —S(O)R
a
or —S(O)
2
R
a
, in which R
a
and R
b
, which may be identical or different, represent an alkyl, alkenyl, alkynyl, acyl, cyano, sulphonyl, carbocyclyl or heterocyclyl radical, each of which may be substituted; or a hydrogen atom;
R
3
represents any one of the groups defined for R
0
;
R
1
and R
2
or R
1
and R
0
or R
3
and R
0
or R
a
and R
b
, taken together with the atoms connecting them, may form an optionally substituted ring, the assembly thus forming a carbocyclyl or heterocyclyl group;
R
4
represents an alkyl, alkenyl, alkynyl, carbocyclyl or heterocyclyl radical, each of which may be substituted; hydroxyl; mercapto; azido; nitro; a halogen atom; cyano; acyl; optionally substituted amino; cyanato, thiocyanato; —SF
5
; —OR
a
; —SR
a
or —Si(R
a
)
3
, in which R
a
is as defined above;
m is an integer chosen from 0, 1, 2 and 3;
R
5
, when it is present, is identical to or different from any one of the other radicals R
5
, and represents any one of the groups defined for R
4
;
R
6
represents an optionally substituted carbocyclyl or heterocyclyl radical; and
A represents 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
)— or —X—A
2
—N(R
9
)—
in which
n represents 0, 1 or 2,
k represents 1 to 9,
A
1
represents —CHR
7
—,
A
2
represents —C(═X)—,
A
3
represents —C(R
8
)═N—O—,
A
4
represents —O—N═C(R
8
)—,
X represents O or S,
X
1
represents O, S, NR
9
or a direct bond,
X
2
represents O, NR
9
or a direct bond,
X
3
represents a hydrogen atom, —C(═O)—, —SO
2
— or a direct bond,
R
7
, which may be identical to or different from any one of the other radicals R
7
, represents an alkyl, alkenyl, alkynyl, cyano, acyl, hydroxyl, alkoxy, haloalkoxy, alkylthio, cycloalkyl or phenyl radical, each of which may be substituted; or represents a hydrogen atom or a halogen atom;
R
8
, which may be identical to or different from any one of the other radicals R
8
, represents an alkyl, alkenyl, alkynyl, alkoxy, alkylthio, carbocyclyl or heterocyclyl radical, each of which may be substituted; or represents a hydrogen atom;
R
9
, which may be identical to or different from any one of the other radicals R
9
, represents an optionally substituted alkyl radical, an optionally substituted carbocyclyl or heterocyclyl radical, a hydrogen atom or an acyl radical; or two groups R
9
in A, taken together with the atoms connecting them, form a 5- to 7-membered ring;
the straight part of the divalent radicals —A— is linked to R
6
;
—A—R
6
and R
5
, taken together with the benzene nucleus M, can form an optionally substituted fused cyclic system.
According to one preferred aspect, the invention relates to the compounds of general formula (I) and the salts thereof, in which:
R
0
represents an alkyl, acyl or cyano radical, each of which may be substituted with alkoxy, haloalkoxy, alkylthio, halogen atoms or phenyl optionally substituted with alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or halogen atoms; or represents a hydrogen atom;
R
1
, R
2
and R
3
are as defined above;
R
4
represents an alkyl, alkenyl, alkynyl, alkoxy or alkylthio radical, each of which may be substituted with alkoxy, haloalkoxy, alkylthio, halogen atoms or phenyl optionally substituted with alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or halogen atoms; or represents hydroxyl; halogen atoms; cyano; acyl (preferably —C(═O)R
c
, —C(═S)R
c
or —S(O)
p
R
c
, in which p represents 0, 1 or 2 and R
c
represents alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, amino, monoalkylamino, dialkylamino or phenyl optionally substituted with alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio; or phenyloxy, phenylthio, carbocyclyl or heterocyclyl);
m represents 0 or 1;
when it is present, R
5
represents a group defined for R
4
according to this characteristic;
A represents a direct bond, or the divalent radicals —O—, —S—, —NR
9
—, —CHR
7
— or —O—CHR
7
—, in which R
9
represents alkyl, alkenyl or alkynyl, each of which may be substituted with alkoxy, haloalkoxy, alkylthio, halogen atoms or phenyl optionally substituted with alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or halogen atoms; or represents a hydrogen atom; and R
7
represents a group defined for R
9
according to this characteristic or represents hydroxyl, halogen atoms, cyano, acyl, alkoxy, haloalkoxy or alkylthio; and
R
6
represents a phenyl or aromatic heterocyclyl radical (preferably thiazolyl, isothiazolyl, thiadiazolyl, pyridyl or pyrimidinyl), optionally substituted with one or more substituents, which may be identical or different, and are chosen from hydroxyl, halogen atoms, cyano, acyl (preferably —C(═O)R
c
, —C(═S)R
c
or —S(O)
p
R
c
, in which p represents 0, 1 or 2 and R
c
represents alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, amino, monoalkylamino, dialkylamino or phenyl optionally substituted with alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio; or phenyloxy, phenylthio, carbocyclyl or heterocyclyl), amino, alkylamino, dialkylamino, alkyl, alkenyl, alkynyl, haloalkyl, R
a
O-alkyl, acyloxyalkyl, cyanooxyalkyl, alkoxy, haloalkoxy, alkylthio, carbocyclyl (preferably cyclohexyl or cyclopentyl) optionally substituted with alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio; and benzyl optionally substituted with alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio.
According to one particularly preferred aspect of the invention, the invention relates to the compounds of general formula (I), and to the salts thereof, as defined above, w

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