Pyrazolyldioxothiochromanoyl derivatives

Details Pyrazolyldioxothiochromanoyl derivatives Pyrazolyldioxothiochromanoyl derivatives

2000-11-08

2001-12-04

Owens, Amelia (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S282000, C548S364400

Reexamination Certificate

active

06326333

ABSTRACT:

The present invention relates to novel pyrazolyldioxothiochromanoyl derivatives of the formula I,
where:
X is oxygen, sulfur, S═O, S(═O)
2
, CR
4
R
5
, C═O or C═NR
6
;
R
1
is hydrogen, nitro, halogen, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-haloalkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-haloalkylsulfonyl, aminosulfonyl, N—(C
1
-C
6
-alkyl)aminosulfonyl, N,N-di(C
1
-C
6
-alkyl)aminosulfonyl, N—(C
1
-C
6
-alkyl-sulfonyl)amino, N—(C
1
-C
6
-haloalkylsulfonyl)amino, N—(C
1
-C
6
-alkyl)-N—(C
1
-C
6
-alkylsulfonyl)amino or N—(C
1
-C
6
-alkyl)-N—(C
1
-C
6
-haloalkylsulfonyl)amino;
R
2
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy;
R
3
is hydrogen, C
1
-C
6
-alkyl or halogen;
R
4
,R
5
are hydrogen, nitro, halogen, cyano, C
1
-C
6
alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-haloalkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-haloalkylsulfonyl, N-C
1
-C
6
-alkylamino, N-C
1
-C
6
-haloalkylamino, N,N-di(C
1
-C
6
-alkyl)amino, N-C
1
-C
6
-alkoxyamino, N—(C
1
-C
6
-alkoxy)-N—(C
1
-C
6
-alkyl)amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl; or
R
4
and R
5
together form an —O—(CH
2
)
m
—O—, —O—(CH
2
)
m
—S—, —S—(CH
2
)
m
—S— or —O—(CH
2
)
n
— chain which may be substituted by one to three radicals selected from the following group: halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxycarbonyl; or
R
4
and R
5
together form a —(CH
2
)
p
— chain which may be interrupted by oxygen or sulfur and/or may be substituted by one to four radicals selected from the following group: halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxycarbonyl; or
R
4
and R
5
together form a methylidene group which may be substituted by one or two radicals selected from the following group: halogen, cyano, hydroxyl, formyl, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-haloalkylsulfinyl, C
1
-C
6
-alkylsulfonyl or C
1
-C
6
-haloalkylsulfonyl;
R
6
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy;
l is 0 to 4;
m is 2 to 4;
n is 1 to 5;
p is 2 to 5;
R
7
is a compound IIa or IIb
 where
R
8
is halogen, OR
11
, SR
11
, SOR
12
, SO
2
R
12
, POR
12
R
13
, OPOR
12
R
13
, OPSR
12
R
13
, NR
14
R
15
, ONR
15
R
15
, N-bonded heterocyclyl or O—(N-bonded heterocyclyl), where the heterocyclyl radical of the two last mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy;
R
9
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
-haloalkyl, hydroxyl, C
1
-C
6
alkoxy or C
1
-C
6
-haloalkoxy;
R
10
is hydrogen, halogen, C
1
-C
6
alkyl, C
1
-C
6
-haloalkyl, hydroxyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylthio or C
1
-C
6
-haloalkylthio;
R
11
is C
1
-C
6
-alkyl, C
3
-C
6
alkenyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-haloalkynyl, C
3
-C
6
-cycloalkyl, C
1
-C
20
alkylcarbonyl, C
2
-C
20
-alkenylcarbonyl, C
2
-C
6
alkynylcarbonyl, C
3
-C
6
-cycloalkylcarbonyl, (2-norbornyl)methylcarbonyl, C
1
-C
6
-alkoxycarbonyl, C
3
-C
6
-alkenyloxycarbonyl, C
3
-C
6
-alkynyloxycarbonyl, C
1
-C
6
-alkylthiocarbonyl, C
1
-C
6
-alkylaminocarbonyl, C
3
-C
6
-alkenylaminocarbonyl, C
3
-C
6
-alkynylaminocarbonyl, N,N-di(C
1
-C
6
-alkyl)aminocarbonyl, N—(C
3
-C
6
-alkenyl)-N—(C
1
-C
6
-alkyl)aminocarbonyl, N—(C
3
-C
6
-alkynyl)-N—(C
3
-C
6
-alkyl)aminocarbonyl, N—(C
1
-C
6
-alkoxy)-N—(C
1
-C
6
-alkyl)aminocarbonyl, N—(C
3
-C
6
-alkenyl)-N—(C
1
-C
6
-alkoxy)aminocarbonyl, N—(C
3
-C
6
-alkynyl)-N—(C
1
-C
6
-alkoxy)aminocarbonyl, di(C
1
-C
6
-alkyl)aminothiocarbonyl, C
1
-C
6
-alkylcarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxyimino-C
1
-C
6
-alkyl, N—(C
1
-C
6
-alkylamino)imino-C
1
-C
6
-alkyl or N,N-di(C
1
-C
6
-alkylamino)imino-C
1
-C
6
alkyl, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, di(C
1
-C
4
-alkyl)amino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
alkoxycarbonyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkoxycarbonyl, di(C
1
-C
4
alkyl)amino-C
1
-C
4
-alkoxycarbonyl, hydroxycarbonyl, C
1
-C
4
-alkylaminocarbonyl, di(C
1
-C
4
-alkyl)aminocarbonyl, aminocarbonyl, C
1
-C
4
-alkylcarbonyloxy or C
3
-C
6
-cycloalkyl;
is phenyl, heterocyclyl, phenyl-C
1
-C
6
-alkyl, heterocyclyl-C
1
-C
6
-alkyl, phenylcarbonyl-C
1
-C
6
-alkyl, heterocyclylcarbonyl-C
1
-C
6
-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxy-thiocarbonyl, heterocyclyloxycarbonyl, heterocyclyloxy-thiocarbonyl, phenylaminocarbonyl, N—(C
1
-C
6
alkyl)-N-(phenyl)aminocarbonyl, heterocyclylaminocarbonyl, N—(C
1
-C
6
-alkyl)-N-(heterocyclyl)aminocarbonyl, phenyl-C
2
-C
6
-alkenylcarbonyl or heterocyclyl-C
2
-C
6
-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
C
4
-alkoxy, C
1
-C
4
-haloalkoxy, phenoxy, heterocyclyl or N-bonded heterocyclyl, where the three lastmentioned substituents for their part may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy;
R
12
, R
13
are C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-haloalkynyl, C
3
-C
6
-cycloalkyl, hydroxyl, C
1
-C
6
-alkoxy, amino, C
1
-C
6
-alkylamino, C
1
-C
6
-haloalkylamino, di(C
1
-C
6
-alkyl)amino or di(C
1
-C
6
-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C
1
-C
4
alkoxy, C
1
-C
4
-alkylthio, di(C
1
-C
4
-alkyl)amino, C
1
-C
4
alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkoxycarbonyl, di(C
1
-C
4
-alkyl)amino-C
1
-C
4
alkoxycarbonyl, hydroxycarbonyl, C
1
-C
4
-alkylaminocarbonyl, di(C
1
-C
4
-alkyl)-aminocarbonyl, aminocarbonyl, C
1
-C
4
-alkylcarbonyloxy or C
3
-C
6
-cycloalkyl;
 are phenyl, heterocyclyl, phenyl-C
1
-C
6
-alkyl, heterocyclyl C
1
-C
6
-alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkoxy;
R
14
is C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-haloalkynyl, C
3
-C
6
-cycloalkyl, hydroxyl, C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, amino, C
1
-C
6
-alkylamino, di(C
1
-C
6
-alkyl)amino or C
1
-C
6
-alkylcarbonylamino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals of the following group: cyano, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, di(C
1
-C
4
-alkyl)amino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkoxycarbonyl, di(C
1
-C
4
-alkyl)amino-C
1
-C
4
-alkoxycarbonyl, hydroxycarbonyl, C
1
-C
4
-alkylaminocarbonyl, di(C
1
-C
4
-alkyl)aminocarbonyl, aminocarbonyl, C
1
-C
4
-alkylcarbonyloxy or C
3
-C
6
-cycloalkyl;
is phenyl, heterocyclyl, phenyl-C
1
-C
6
-alkyl or heterocyclyl-C
1
-C
6
-alkyl, where the phenyl or heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-al

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