Phosphoric benzoyl derivatives and their use as herbicides

Details Phosphoric benzoyl derivatives and their use as herbicides Phosphoric benzoyl derivatives and their use as herbicides

2001-10-29

2003-09-02

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C568S017000

Reexamination Certificate

active

06613717

ABSTRACT:

The present invention relates to phosphorus-containing benzoyl derivatives of the formula I
in which:
X is oxygen or sulfur;
R
1
,R
2
are hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, hydroxyl, C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, mercapto, C
1
-C
6
-alkylthio, C
3
-C
6
-alkenylthio, C
3
-C
6
-alkynylthio, amino, C
1
-C
6
-alkylamino, di(C
1
-C
6
-alkyl)amino, (C
1
-C
6
-alkoxy)(C
1
-C
6
-alkyl)amino, (C
3
-C
6
-alkenyl)(C
1
-C
6
-alkyl)amino, (C
3
-C
6
-alkynyl)(C
1
-C
6
-alkyl)amino, di(C
3
-C
6
-alkenyl)amino or di(C
3
-C
6
-alkynyl)amino, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulfinyl, C
1
-C
4
-alkylsulfonyl, di(C
1
-C
4
-alkyl)amino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl, phenyl or heterocyclyl, where the the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one to three of the following groups:
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;
 are phenyl or phenoxy which may be partially or fully halogenated and/or may carry one to three of the following groups:
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; or
R
1
and R
2
together form an —O—(CH
2
)
m
—O—, —O—(CH
2
)
m
—S—, —S—(CH
2
)
m
—S—, —NR
5
—(CH
2
)
m
—NR
5
—, —O—(CH
2
)
m
—NR
5
—, —S—(CH
2
)
m
—NR
5
—, —(CH
2
)
n
—O—, —(CH
2
)
n
—S— or —(CH
2
)
n
—NR
5
chain which may carry one to three radicals from the following group:
halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkoxycarbonyl or phenyl which is unsubstituted or partially or fully halogenated and/or may carry one to three of the following groups:
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; or
R
1
and R
2
together form a —(CH
2
)
p
chain which may be interrupted by oxygen, sulfur or NR
5
and/or may carry one to three radicals from the following group:
halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkoxycarbonyl or phenyl which is unsubstituted or partially or fully halogenated and/or may carry one to three of the following groups: 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
3
is hydrogen, nitro, cyano, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-haloalkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio-C
1
-C
6
-alkyl, C
1
-C
6
-alkylsulfinyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylsulfonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, 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, C
1
-C
6
-alkylaminosulfonyl, di(C
1
-C
6
-alkyl)aminosulfonyl, (C
1
-C
6
-alkylsulfonyl)amino, (C
1
-C
6
-haloalkylsulfonyl)amino, N—(C
1
-C
6
-alkyl)—N—(C
1
-C
6
-alkylsulfonyl)amino, N—(C
1
-C
6
-alkyl)—N—(C
1
-C
6
-haloalkylsulfonyl)amino, —P(═X)R
1
R
2
, phenyl or heterocyclyl, where the two last-mentioned radicals may be partially or fully halogenated and/or may carry one to three of the following groups:
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
4
is nitro, cyano, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfinyl or C
1
-C
6
-alkylsulfonyl;
R
5
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl or C
1
-C
6
-alkoxy;
l is 0, 1 or 2;
m is 2, 3 or 4;
n is 3, 4 or 5;
p is 4, 5 or 6;
Q is a radical of the formula Q
1
, Q
2
, Q
3
or Q
4
R
6
is hydroxyl, mercapto, halogen, OR
13
, SR
13
, SOR
14
, SO
2
R
14
, OSO
2
R
14
, POR
15
R
16
, OPR
15
R
16
, OPOR
15
R
16
, OPSR
15
R
16
, NR
17
R
18
, ONR
18
R
19
, 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
7
,R
9
,R
11
are hydrogen, 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
-alkoxycarbonyloxy, 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;
R
8
,R
10
,R
12
are hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio or C
1
-C
6
-alkoxycarbonyl; or
R
7
and R
8
or R
9
and R
10
or R
11
and R
12
together form an —O—(CH
2
)
u
—O—, —O—(CH
2
)
u
—S—, —S—(CH
2
)
u
—S—, —O—(CH
2
)
v
— or —S—(CH
2
)
v
chain which may be substituted by one to three radicals from the following group:
halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxycarbonyl; or
R
7
and R
8
or R
9
and R
10
or R
11
and R
12
together form a —(CH
2
)
w
chain which may be interrupted by oxygen or sulfur and/or may be substituted by one to four radicals from the following group:
halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxycarbonyl; or
R
7
and R
8
or R
9
and R
10
or R
11
and R
12
together form a methylidene group which may be substituted by one to two radicals 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; or
R
7
and R
8
or R
9
and R
10
or R
11
and R
12
together with the carbon atom to which they are attached form a carbonyl group; or
R
7
and R
9
or R
9
and R
11
or R
7
and R
11
together form a —(CH
2
)
v
chain which may be substituted by one to three radicals from the following group:
halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, hydroxyl or C
1
-C
6
-alkoxycarbonyl;
R
13
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
-alkylaminocarbonyl, C
1
-C
6
-alkylcarbonyl-C
1
-C
6
-alkyl or C
1
-C
6
-alkoxyimino-C
1
-C
6
-alkyl, where the abovementioned alkyl and cycloalkyl 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, heterocyclylcarbonyl, phenylaminocarbonyl or heterocyclylaminocarbonyl, where the phenyl and the heterocyclyl radical of the 8 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
14
,R
15
, R
16
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

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