Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2001-06-21
2003-07-29
Raymond, Richard L. (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S292000, C504S310000, C504S313000, C504S326000, C504S333000, C549S023000, C549S397000, C558S415000, C560S256000, C564S374000, C564S384000, C568S031000, C568S042000, C568S327000
Reexamination Certificate
active
06599861
ABSTRACT:
The present invention relates to novel herbicidally active benzoyl derivatives, to processes for their preparation, to compositions comprising said compounds, and to the use thereof for controlling weeds, in particular in crops of cultivated plants or for inhibiting plant growth.
Benzoyl derivatives with herbicidal activity are described for example in U.S. Pat. No. 5,094,685. Now, novel benzoyl derivatives with herbicidal and growth-inhibiting properties have been found.
The objects of the present invention are thus compounds of formula I
wherein
X is L
1
-Y
1
-R
4
, L
2
-Y
2
-L
3
-Y
3
-R
5
or L
4
-Y
4
-L
5
-Y
5
-L
6
-Y
6
-R
6
;
L
1
,L
2
, L
3
, L
4
, L
5
, L
6
, independently of one another, signify C
1
-C
6
-alkylene, which may be substituted by C
1
-C
4
-alkyl, halogen, C
1
-C
4
-alkoxy, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl; or C
3
-C
6
-alkenylene, which may be substituted by C
1
-C
4
-alkyl, halogen, C
1
-C
4
-alkoxy, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl; or C
3
-C
6
-alkynylene, which may be substituted by C
1
-C
4
-alkyl, halogen, C
1
-C
4
-alkoxy, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl;
Y
1
, Y
3
, Y
6
, independently of one another, signify oxygen, sulphur, SO, SO
2
, NR
7
, OC(O), NR
8
SO
2
or OSO
2
;
Y
2
, Y
4
, Y
5
, independently of one another, signify oxygen, sulphur, SO, SO
2
, NR
9
, OC(O) or NR
10
SO
2
;
R
7
, R
8
, R
9
and R
10
, independently of one another, signify hydrogen or C
1
-C
6
-alkyl;
R
1
and R
2
, independently of one another, signify halogen, cyano, nitro, amino, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
6
-halogenalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulphinyl, C
1
-C
6
-alkylsulphonyl, C
1
-C
6
-dialkylaminosulphonyl, C
1
-C
6
-alkylaminosulphonyl, C
1
-C
4
-alkylsulphonylamino, C
1
-C
6
-halogenalkoxy, OSO
2
—C
1
-C
4
-alkyl, C
1
-C
6
-halogenalkylthio, C
1
-C
6
-halogenalkylsulphinyl, C
1
-C
6
-halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl;
R
3
signifies hydrogen, C
1
-C
4
-alkyl or halogen;
R
4
, R
5
and R
6
, independently of one another, signify hydrogen, C
1
-C
6
-alkyl, which may be substituted by the group A
1
; C
3
-C
7
-cycloalkyl, which may be substituted by the group A
2
;
C
3
-C
7
-cycloalkyl, which may be interrupted by 1 to 2 oxygen atoms, sulphur or NR
11
; C
2
-C
6
-alkenyl, which may be substituted by the group A
3
; C
3
-C
6
-alkynyl, which may be substituted by the group A
4
; C
3
-C
7
-cycloalkyl-C
1
-C
4
-alkyl, whereby the cycloalkyl group may be interrupted by 1 to 2 oxygen atoms, sulphur or NR
12
; benzyl or phenyl which may in turn be substituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenalkyl, cyano, nitro, C
1
-C
4
-halogenalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkylsulphonyl, C
1
-C
4
-dialkylamino, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-dialkylaminosulphonyl or NR
13
—CO—R
14
;
R
11
and R
12
, independently of one another, signify hydrogen or C
1
-C
4
-alkyl;
R
13
and R
14
, independently of one another, signify hydrogen or C
1
-C
4
-Alkyl;
A
1
, A
2
, A
3
, A
4
, independently of one another, are hydroxy, formyl, COOH, C
1
-C
6
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkylsulphonyl, OSO
2
—C
1
-C
4
-alkyl, C
1
-C
6
-alkylamino, C
1
-C
6
-dialkylamino, C
1
-C
6
-alkylaminocarbonyl, C
1
-C
6
-dialkylaminocarbonyl, nitro, halogen, cyano, C
1
-C
4
-alkoxyhalogen, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl or phenyl, whereby the phenyl group may in turn be substituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenalkyl, cyano, nitro, C
1
-C
4
-halogenalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkylsulphonyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-dialkylaminosulphonyl or NR
15
—CO—R
16
;
R
15
and R
16
, independently of one another, signify hydrogen or C
1
-C
4
-alkyl;
Q is the group Q
1
wherein R
39
signifies hydroxy, halogen, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylcarbonyloxy, C
1
-C
6
-alkoxycarbonyloxy, C
1
-C
6
-dialkylamino, COOH, C
1
-C
6
-alkenylthio, C
1
-C
6
-alkenylsulphinyl, C
1
-C
6
-alkenylsulphonyl, OSO
2
—C
1
-C
6
-alkyl, benzoyloxy or OSO
2
-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C
1
-C
4
-alkyl, C
1
-C
4
-halogenalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenalkoxy, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl, halogen, nitro, COOH or cyano; V is C
1
-C
4
-alkylene, oxygen, sulphur, SO or SO
2
;
R
17
, R
18
, R
19
, R
20
, R
21
and R
22
, independently of one another, signify hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulphinyl, C
1
-C
6
-alkylsulphonyl, C
1
-C
4
-alkylaminosulphonyl, C
1
-C
4
-halogenalkyl, C
1
-C
4
-alkylamino, C
1
-C
4
-dialkylamino, C
1
-C
6
-alkoxy, cyano, nitro, halogen or phenyl, q is 1 or 2;
or Q is the group Q
2
wherein
R
23
signifies hydroxy, halogen, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylcarbonyloxy, C
1
-C
6
-alkoxycarbonyloxy, C
1
-C
6
-dialkylamino, COOH, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulphinyl, C
1
-C
6
-alkylsulphonyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkylthio, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkylsulphonyl, C
1
-C
6
-alkenylthio, C
1
-C
6
-alkenylsulphinyl, C
1
-C
6
-alkenylsulphonyl, OSO
2
—C
1
-C
6
-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO
2
-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C
1
-C
4
-alkyl, C
1
-C
4
-halogenalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenalkoxy, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl, halogen, nitro, COOH or cyano; R
24
and R
25
, independently of one another, signify hydrogen, hydroxy, C
1
-C
6
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulphinyl, C
1
-C
6
-alkylsulphonyl, C
1
-C
4
-alkylaminosulphonyl, C
1
-C
4
-halogenalkyl, C
1
-C
6
-alkylamino, C
1
-C
6
-dialkylamino, C
1
-C
6
-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C
1
-C
4
-alkyl, C
1
-C
4
-halogenalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenalkoxy, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl, amino, C
1
-C
4
-alkylamino, C
1
-C
4
-dialkylamino, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulphinyl, C
1
-C
6
-alkylsulphonyl, C
1
-C
4
-alkyl-S(O)
2
O, C
1
-C
4
-halogenalkylthio, C
1
-C
4
-halogenalkylsulphinyl, C
1
-C
4
-halogenalkylsulphonyl, C
1
-C
4
-halogenalkyl-S(O)
2
O, C
1
-C
4
-alkyl-S(O)
2
NH, C
1
-C
4
-alkyl-S(O)
2
N(C
1
-C
4
-alkyl), halogen, nitro, COOH or cyano; or R
24
and R
25
together form a C
2
-C
6
-alkylene bridge, R
26
signifies hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxycarbonyl or phenyl, which may in turn be substituted by C
1
-C
6
-alkyl, C
1
-C
6
-halogenalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenalkoxy, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, amino, C
1
-C
4
-alkylamino, C
1
-C
4
-dialkylamino, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulphinyl, C
1
-C
6
-alkylsulphonyl, C
1
-C
4
-alkyl-S(O)
2
O, C
1
-C
4
-halogenalkylthio, C
1
-C
4
-halogenalkylsulphinyl, C
1
-C
4
-halogenalkylsulphonyl, C
1
-C
4
-halogenalkyl-S(O)
2
O, C
1
-C
4
-alkyl-S(O)
2
NH, C
1
-C
4
-alkyl-S(O)
2
N(C
1
-C
4
-alkyl), halogen, nitro, COOH or cyano;
or Q is the group Q
3
wherein
R
27
signifies hydroxy, halogen, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylcarbonyloxy, C
1
-C
6
-alkoxycarbonyloxy, C
1
-C
6
-dialkylamino, COOH, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulphinyl, C
1
-C
6
-alkylsulphonyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkylthio, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkylsulphonyl, C
1
-C
6
-alkenylthio, C
1
-C
6
-alkenylsulphinyl, C
1
-C
6
-alkenylsulphonyl, OSO
2
—C
1
-C
6
-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO
2
-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C
1
-C
4
-alkyl, C
1
-C
4
-halogenalkyl, C
1
-C
4
-alkoxy
De Mesmaeker Alain
Lee Shy-Fuh
Schaetzer Jürgen
Hamilton Thomas
Raymond Richard L.
Syngenta Participations (AG)
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