Cyclohexenonedioxothiochromanoyl derivatives

Details Cyclohexenonedioxothiochromanoyl derivatives Cyclohexenonedioxothiochromanoyl derivatives

2000-10-30

2002-08-27

Owens, Amelia (Department: 1625)

Plant protecting and regulating compositions

Seed coated with agricultural chemicals other than fertilizers

C504S225000, C504S242000, C504S248000, C504S251000, C504S271000, C504S272000, C504S275000, C504S280000, C504S283000, C504S288000, C549S005000, C549S015000, C549S023000, C548S247000, C548S268600, C548S311700, C548S315100, C548S364400, C548S525000, C548S526000, C546S197000, C546S202000, C546S280100, C544S145000, C544S146000, C544S318000

Reexamination Certificate

active

06440899

ABSTRACT:

The present invention relates to novel cyclohexenonedioxothiochromanoyl 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
-alkylsulfonyl)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-tetra-hydropyrrolyl, 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, hydroxyl, formyl, 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 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
10
, SR
10
, SOR
11
, SO
2
R
11
, OSO
2
R
11
, POR
11
R
12
, OPOR
11
R
12
, OPSR
11
R
12
, NR
13
R
14
, ONR
14
R
14
, N-bonded heterocyclyl or O—(N-bonded heterocyclyl), where the heterocyclyl radical of the two 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
9
is nitro, halogen, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, di(C
1
-C
6
-alkoxy)methyl, di(C
1
-C
6
-alkylthio)methyl, (C
1
-C
6
-alkoxy)(C
1
-C
6
-alkylthio)methyl, hydroxyl, 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, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-haloalkylcarbonyl, C
1
-C
6
-alkoxycarbonyl or C
1
-C
6
-haloalkoxycarbonyl; or
two radicals R
9
which are attached to the same carbon 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
two radicals R
9
which are attached to the same carbon 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
two radicals R
9
which are attached to the same carbon together form a methylidene group which may be substituted by one to two radicals selected from the following group:
halogen, hydroxyl, formyl, 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; or
two radicals R
9
which are attached to the same carbon together with this carbon form a carbonyl group; or
two radicals R
9
which are attached to different carbons together form a —(CH
2
)
n
— chain which may be substituted by one to three radicals selected from the following group:
halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, hydroxyl or C
1
-C
6
-alkoxycarbonyl;
R
10
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
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, 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, phenyloxythiocarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, 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 or C
1
-C
4
-haloalkoxy;
R
11
, R
12
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)aminno-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 hete

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