Tricyclic benzoylcyclohexanedione derivatives

Details Tricyclic benzoylcyclohexanedione derivatives Tricyclic benzoylcyclohexanedione derivatives

2001-11-29

2003-06-24

Aulakh, Charanjit S. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S242000, C548S151000, C548S218000, C548S302100, C548S359500, C504S266000, C504S270000, C504S276000, C504S281000

Reexamination Certificate

active

06583089

ABSTRACT:

This application is a 371 of PCT/EP 00/04806 filed May 26, 2000, now WO 00/73311, Dec. 7, 2000.
The present invention relates to novel tricyclic benzoylcyclohexanedione derivatives of the formula I
where:
X is oxygen, sulfur, S═O, S(═O)
2
, CR
6
R
7
, NR
8
or a bond;
Y together with the two carbons to which it is attached forms a saturated, partially saturated or unsaturated 5- or 6-membered heterocycle which contains one to three identical or different heteroatoms selected from the following group: oxygen, sulfur or nitrogen;
R
1
,R
2
,R
6
,R
7
are hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy;
R
3
is halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy;
R
4
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
5
is hydrogen, C
1
-C
6
-alkyl or halogen;
R
8
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylcarbonyl, formyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-haloalkoxycarbonyl, C
1
-C
6
-alkylsulfonyl or C
1
-C
6
-haloalkylsulfonyl;
m is 0, 1 or 2;
R
9
is a radical IIa or IIb
 where:
R
10
is hydroxyl, mercapto, halogen, OR
17
, SR
17
, SOR
18
, SO
2
R
18
, OSO
2
R
18
, NR
19
R
20
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
11
, R
15
are hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxycarbonyl;
R
12
, R
14
, R
16
are hydrogen or C
1
-C
4
-alkyl;
R
13
is hydrogen, halogen, hydroxyl, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, di-(C
1
-C
6
-alkoxy)methyl, (C
1
-C
6
-alkoxy)-(C
1
-C
6
-alkylthio)methyl, di-(C
1
-C
6
-alkylthio)methyl, 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
-alkoxycarbonyl, C
1
-C
6
-haloalkoxycarbonyl;
is 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3 oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the six last-mentioned radicals may be substituted by one to three C
1
-C
4
-alkyl radicals; or
R
12
and R
13
or R
13
and R
16
together form a &pgr;-bond or a C
1
-C
5
-alkyl chain which may carry 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
12
and R
16
together form a C
1
-C
4
-alkyl chain which may carry 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
13
and R
14
together form a —O—(CH
2
)
p
—O—, —O—(CH
2
)
p
—S—, —S—(CH
2
)
p
—S—, —O—(CH
2
)
q
— or —S—(CH
2
)
q
— 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
13
and R
14
together with the carbon to which they are attached form a carbonyl group;
R
17
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
-alkoxyimino-C
1
-C
6
-alkyl, where the alkyl, cycloalkyl or alkoxy radicals mentioned 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, phenoxythiocarbonyl, phenylaminocarbonyl, N—(C
1
-C
6
-alkyl)-N-phenylaminocarbonyl, 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-heterocyclylaminocarbonyl or heterocyclyl-C
1
-C
6
-alkenylcarbonyl, where the phenyl or 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
17
[sic] 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 radicals mentioned 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
4
-alkyl, heterocyclyl or heterocyclyl-C
1
-C
4
-alkyl, where the phenyl or 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
19
is hydrogen, 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, hydroxyl, C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, amino, C
1
-C
6
-alkylamino, di-(C
1
-C
6
-alkyl)amino or C
1
-C
6
-alkylcarbonylamino, where the alkyl, cycloalkyl or alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following radicals: cyano, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkylaminocarbonyl, di-(C
1
-C
4
-alkyl)aminocarbonyl or C
3
-C
6
-cycloalkyl;
is phenyl, phenyl-C
1
-C
4
-alkyl, phenylcarbonyl, heterocyclyl, heterocycly-C
1
-C
4
-alkyl [sic] or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six 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
20
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
p is 2, 3 or 4;
q is 1, 2, 3, 4 or 5;
and their agriculturally useful salts.
Moreover, the invention relates to processes for preparing compounds of the formula I, to compositions comprising them and to the use of these derivatives or of the compositions comprising them for controlling harmful plants.
WO 97/19087 and EP-A 860 441 disclose tricyclic compounds which are characterized in that the benzoyl unit that they contain in each case is fused to a bicycle via positions 3 and 4. However, the herbicidal properties of the prior-art compounds and their compatibility with crop plants are not entirely satisfactory.
It is an object of the present in

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