Substituted 3-phenyluracils

Details Substituted 3-phenyluracils Substituted 3-phenyluracils

1997-01-03

2001-05-29

Morris, Patricia L. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Abscission agent, defoliant, or desiccant

C504S243000, C544S311000, C544S312000, C544S313000, C544S314000

Reexamination Certificate

active

06239074

ABSTRACT:

The present invention relates to novel substituted 3-phenyluracils of the general formula I
where
X
1
and X
2
are each oxygen or sulfur;
W is —C(R
8
)═X
5
, —C(R
8
)(X
3
R
6
)(X
4
R
7
) , —C(R
8
)═C(R
9
)—CN, —C(R
8
)—C(R
9
)—CO—R
10
, —CH(R
8
)—CH(R
9
)—CO—R
10
, —C(R
8
)═C(R
9
)—CH
2
—CO—R
10
1
—C(R
8
)═C(R
9
)—C(R
11
)═C(R
12
)—CO—R
10
or —C(R
8
)═C(R
9
)—CH
2
—CH (R
13
)—CO—R
10
where
X
3
and X
4
are each oxygen or sulfur;
X
5
is oxygen, sulfur or a radical—NR
14
;
R
14
is hydrogen, hydroxyl, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
7
-cycloalkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, C
5
-C
7
-cycloalkoxy, C
5
-C
7
-cyclo-alkenyloxy, C
1
-C
6
-haloalkoxy, C
3
-C
6
-haloalkenyloxy, hydroxy-C
1
-C
6
-alkoxy, cyano-C
1
-C
6
-alkoxy, C
3
-C
7
-cyclo-alkyl-C
1
-C
6
-alkoxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkoxy, C
1
-C
6
-alkoxy-C
3
-C
6
-alkenyloxy, C
1
-C
6
-alkylcarbonyloxy, C
1
-C
6
-haloalkylcarbonyloxy, C
1
-C
6
-alkylcarbamoyloxy, C
1
-C
6
-haloalkylcarbamoyloxy-C
1
-C
6
-alkoxycarbonyl-C
2
-C
6
-alkoxy, C
1
-C
6
-alkylthio-C
1
-C
6
-alkoxy, di-C
1
-C
6
-alkyl-amino-C
1
-C
6
-alkoxy, phenyl which may carry from one to three of the following substituents: cyano, nitro, halogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl, phenyl-C
1
-C
6
-alkoxy, phenyl-C
3
-C
6
-alkenyloxy or phenyl-C
3
-C
6
-alkynyloxy, where one or two methylene groups of each of the carbon chains may be replaced with —O—, —S— or —N(C
1
-C
6
-alkyl)- and each phenyl ring may carry from one to three of the following substituents: cyano, nitro, halogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl, heterocyclyl, heterocyclyl-C
3
-C6-alkoxy, heterocyclyl-C
3
-C
6
-alkenyloxy or heterocyclyl-C
1
-C
6
-alkynyloxy, where one or two methylene groups of each of the carbon chains may be replaced with —O—, —S— or —N(C
1
-C
6
-alkyl)- and the heterocyclyl ring may be from three-membered to seven-membered and saturated, unsaturated or aromatic and may contain from one to four hetero atoms selected from the group consisting of one or two oxygen or sulfur atoms and up to four nitrogen atoms and furthermore may carry from one to three of the following substituents: cyano, nitro, halogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-alkoxycarbonyl, or —N(R
15
)R
16
, where
P
15
and R
16
are each hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-halo-alkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
6
-alkyl or C
1
-C
6
-alkoxycarbonyl-C
2
-C
6
-alkenyl, where the alkenyl chain may additionally carry from one to three of the following radicals: halogen and cyano or phenyl which may carry from one to three of the following substituents: cyano, nitro, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
,-alkenyl, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl, or
P
15
and R
16
together with the common nitrogen atom form a saturated or unsaturated 4-membered to 7-membered heterocyclic structure, where one ring member may be replaced with —O—, —S—, —N—, —NH— or —N (C
1
-C
6
-alkyl)—;
R
6
and R
7
are each C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl or C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, or
R
6
and R
7
together form a saturated or unsaturated, two-membered to four-membered carbon chain which may carry an oxo substituent, where one member of this chain may be replaced with an oxygen, sulfur or nitrogen atom which is not adjacent to X
3
and X
4
, and where the chain may carry from one to three of the following radicals: cyano, nitro, amino, halogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkynyloxy, C
1
-C
6
-haloalkyl, cyano-C
1
-C
6
-alkyl, hydroxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyloxy-C
1
-C
6
-alkyl, C
3
-C
6
-alkynyloxy-C
1
-C
6
-alkyl, C
3
-C
7
-cycloalkyl, C
3
-C
7
-cycloalkoxy, carboxyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylcarbonyl-oxy-C
1
-C
6
-alkyl and phenyl which may carry from one to three of the following radicals: halogen, cyano, nitro, amino, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl, and where the chain may furthermore be substituted by a fused-on or spiral-bonded three-membered to seven-membered ring, and one or two carbon atoms of this ring may be replaced with oxygen, sulfur and unsubstituted or C
1
-C
6
-alkyl-substituted nitrogen atoms and this ring may carry one or two of the following substituents: cyano, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy, C
2
-C
6
-cyanoalkyl, C
1
-C
6
-haloalkyl and C
1
-C
6
-alkoxycarbonyl;
R
8
is hydrogen, cyano, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-haloalkyl, C
3
-C
7
-cycloalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl or C
1
-C
6
-alkoxycarbonyl;
R
9
and R
12
are each hydrogen, cyano, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halo-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonyl or C
1
-C
6
-alkoxycarbonyl;
R
10
is hydrogen, O—R
17
, S—R
17
or C
1
-C
6
-alkyl which may furthermore carry one or two C
1
-C
6
-alkoxy substituents or
R
10
is C
3
—C
6
-alkenyl, C
3
—C
6
-alkynyl, C
1
-C
6
-haloalkyl, C
3
-C
7
-cycloalkyl, C
1
-C
6
-alkylthio-C
2
-C
6
-alkyl, C
2
-C
6
-alkylimino-oxy, —N(R
15
)R
16
or phenyl which may carry from one to three of the following substituents: cyano, nitro, halogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-alkoxycarbonyl;
R
17
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
7
-cycloalkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-haloalkenyl, cyano-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio-C
1
-C
6
-alkyl, C
1
-C
6
-alkyl-oximino-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylcarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
6
-alkyl, phenyl or phenyl-C
1
-C
6
-alkyl, where each of the phenyl radicals in turn may carry from one to three of the following substituents: cyano, nitro, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl;
R
11
is hydrogen, cyano, halogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
2
-C
6
-alkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, —NR
18
R
19
, where R
18
and R
19
have the same meanings as R
15
and R
16
, or phenyl which may furthermore carry from one to three of the following substituents: cyano, nitro, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl;
R
13
is hydrogen, cyano, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxycarbonyl;
or R
9
and R
10
together form a two-membered to five-membered carbon chain in which one carbon atom may be replaced with oxygen, sulfur or unsubstituted or C
1
-C
6
-alkyl-substituted nitrogen;
R
1
is halogen, cyano, nitro or trifluoromethyl;
R
2
is hydrogen or halogen;
R
3
is hydrogen, nitro, C
1
-C
6
-alkyl, C
1
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkylcarbonyl, cyano-C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, formyl, C
1
-C
6
-alkanoyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-haloalkylcarbonyl, C
1
-C
6
-alkylcarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
6
-alkyl;
a group —N(R
20
)R
21
where R
20
and R
21
have one of the meanings of R
15
and R
16
; phenyl or phenyl-C
1
-C
6
-alkyl, where each phenyl ring may carry from one to three of the following radicals: cyano, nitro, halogen, C
1
-C
6
-alkyl, C
6
-C
6
-alkenyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl;
R
4
is hydrogen, cyano, nitro, halogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
3
-C
8
-cycloalkyl, C
1
-C
6
-h

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