Thiochromanoylpyrazolone derivatives

Details Thiochromanoylpyrazolone derivatives Thiochromanoylpyrazolone derivatives

2001-05-31

2002-03-05

Ramsuer, Robert W. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S140000, C548S119000, C548S159000, C548S255000, C548S266400, C548S364400

Reexamination Certificate

active

06352959

ABSTRACT:

The present invention relates to novel thiochromanoylpyrazolone derivatives of the formula I
where:
A is C
1
-C
6
-alkanediyl, C
2
-C
6
-alkenediyl, C
4
-C
6
-alkadienediyl or C
2
-C
6
-alkinediyl, where the abovementioned radicals may carry one or two substituents from the following group: cyano, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylcarbonyl or C
1
-C
4
-alkoxycarbonyl;
R
1
is cyano, thiocyanato, nitro, OR
4
, SR
5
, SOR
6
, SO
2
R
6
, ONR
6
R
7
, ON═CR
6
R
8
, NR
9
R
10
, P(O)R
11
R
12
, P(S)R
11
R
12
, COR
6
, CO
2
R
6
, phenyl, heterocyclyl or N-bonded heterocyclyl, where the three last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one to three substituents from the following group: nitro, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy or C
1
-C
4
-alkoxycarbonyl;
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, halogen or C
1
-C
6
-alkyl;
X is oxygen, sulfur, S═O, S(═O)
2
, CR
13
R
14
, C═O or C═NR
15
;
m is 0, 1 or 2;
n is 0, 1, 2, 3 or 4;
R
4
, R
5
are one of the radicals mentioned under R
6
;
are hydrogen, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-haloalkylcarbonyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-haloalkoxycarbonyl, C
1
-C
4
-alkylsulfonyl, C
1
-C
4
-haloalkylsulfonyl, P(O)R
11
R
12
or P(S)R
11
R
12
;
are phenylcarbonyl, phenoxycarbonyl, phenyl-C
1
-C
4
-alkylcarbonyl, phenylsulfonyl, phenoxysulfonyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyl-C
1
-C
4
-alkylcarbonyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl, where the phenyl and the heterocyclyl radical of the ten 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, C
1
-C
4
-haloalkoxy or C
1
-C
4
-alkoxycarbonyl;
R
6
is C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl or C
3
-C
6
-cycloalkyl, where the four abovementioned 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
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkylsulfinyl, C
1
-C
4
-haloalkylsulfinyl, C
1
-C
4
-alkylsulfonyl, C
1
-C
4
-haloalkylsulfonyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl and C
1
-C
4
-haloalkoxycarbonyl;
is phenyl, phenyl-C
1
-C
4
-alkyl, heterocyclyl or heterocyclyl-C
1
-C
4
-alkyl, where the phenyl and the heterocyclyl radical of the four 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, C
1
-C
4
-haloalkoxy or C
1
-C
4
-alkoxycarbonyl;
R
7
is hydrogen or C
1
-C
6
-alkyl;
R
8
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl, cyano or C
1
-C
6
-alkoxy;
R
9
is one of the radicals mentioned under R
4
; is C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, aminocarbonyl, N—C
1
-C
6
-alkylaminocarbonyl or N,N-di-(C
1
-C
6
-alkyl)aminocarbonyl;
R
10
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
R
11
, R
12
are hydrogen, hydroxyl, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, phenyl, phenyl-C
1
-C
4
-alkyl or phenoxy, where the three 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, C
1
-C
4
-haloalkoxy or C
1
-C
4
-alkoxycarbonyl;
R
13
, R
14
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
13
, R
14
together form a methylidene group which may be substituted by one or two substituents from the following group: halogen, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy;
R
15
is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy;
R
16
is a radical IIa or IIb,
where:
R
17
is hydroxyl, mercapto, halogen, OR
20
, SR
20
, SOR
21
, SO
2
R
21
, OSO
2
R
21
, P(O)R
22
R
23
, OP(O)R
22
R
23
, P(S)R
22
R
23
, OP(S)R
22
R
23
, NR
24
R
25
, ONR
21
R
21
or N-bonded heterocyclyl which 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
18
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
19
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
20
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
6
-alkylcarbonyl, C
2
-C
6
-alkenylcarbonyl, C
2
-C
6
-alkynylcarbonyl, C
3
-C
6
-cycloalkylcarbonyl, 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
1
-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 or C
1
-C
6
-alkoxyimino-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, 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, phenyl-C
1
-C
6
-alkyl, phenylcarbonyl-C
1
-C
6
-alkyl, phenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl, N—(C
1
-C
6
-alkyl)-N-(phenyl)aminocarbonyl, phenyl-C
2
-C
6
-alkenylcarbonyl, heterocyclyl, heterocyclyl-C
1
-C
6
-alkyl, heterocyclylcarbonyl-C
1
-C
6
-alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N—(C
1
-C
6
-alkyl)-N-(heterocyclyl)aminocarbonyl or heterocyclyl-C
2
-C
6
-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 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
21
is C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl or C
3
-C
6
-cycloalkyl, where the four abovementioned 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
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl or C
1
-C
4
-haloalkoxycarbonyl;
is phenyl, phenyl-C
1
-C
6
-alkyl, heterocyclyl or heterocyclyl-C
1
-C
6
-alkyl, where the phenyl and the heterocyclyl radical of the 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, C
1
-C
4
-haloalkoxy or C
1
-C
4
-alkoxycarbonyl;
R
22
, R
23
is hydrogen, hydroxyl, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio,

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