Benzohetero cyclylcyclo hexenones and their use as herbicides

Details Benzohetero cyclylcyclo hexenones and their use as herbicides Benzohetero cyclylcyclo hexenones and their use as herbicides

2001-11-07

2003-07-08

Chang, Ceila (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S179000

Reexamination Certificate

active

06589915

ABSTRACT:

This application is a 371 of PCT/EP00/04042 May 5, 2000.
The present invention relates to cyclohexenone derivatives of benzo-fused unsaturated 5-membered nitrogen heterocycles, to processes for preparing such cylohexenone derivatives, to compositions comprising such compounds, and to the use of the cyclohexenone derivatives or of the compositions comprising them for controlling harmful plants.
WO 96/05182 discloses saccharin derivatives having herbicidal action which are substituted on the benzene ring of the saccharin skeleton by a (2-cyclohexane-1,3-dione)carbonyl radical.
WO 99/03845 discloses cyclohexane-1,3-diones which have a benzoyl radical in the 2-position. The benzoyl radical for its part can be substituted by heteroaromatic compounds. The compounds have herbicidal action.
WO 97/09324 discloses cyclohexane-1,3-diones having herbicidal action which have a benzo-fused sulfur heterocycle, for example a thiochromane or a benzodihydrothiophene radical, which is attached via a carbonyl group, in the 2-position.
EP-A 283 261 discloses similar compounds in which the cyclohexenone ring is substituted in the 2-position by a heteroaromatic radical. The heteroaromatic radicals mentioned are sulfur-, nitrogen- and/or oxygen-containing 5-membered or 6-membered heterocycles.
However, the herbicidal properties of the compounds known from the publications mentioned and their compatibility with crop plants do not meet all of the criteria required from herbicides.
It is an object of the present invention to provide novel compounds having herbicidal action which preferably have greater activity than the herbicidal substances of the prior art and/or better selectivity with respect to harmful plants.
We have found that this object is achieved by cyclohexenone derivatives of benzo-fused unsaturated 5-membered nitrogen heterocycles of the formula I defined below.
Consequently, the present invention relates to cyclohexenone derivatives of benzo-fused unsaturated 5-membered nitrogen heterocyles of the formula I,
in which
X is N or a group C—R
3
;
Y is O, S, SO, SO
2
or NR
4
or
X-Y is S═N, and X is sulfur;
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, C
1
-C
6
-alkoxy-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
-alkylamino-C
1
-C
6
-alkyl, or di-(C
1
-C
6
-alkyl)amino-C
1
-C
6
-alkyl;
R
2
is hydrogen, halogen or C
1
-C
6
-alkyl;
R
3
is hydrogen, halogen, nitro, cyano, hydroxyl, amino, mercapto, thiocyanato, hydrazide, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-hydroxyalkyl, C
1
-C
6
-aminoalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-hydroxyalkoxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkoxy, C
3
-C
6
-cycloalkyl,
is C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
3
-C
6
-cycloalkylamino, where the alkyl and cycloalkyl groups of the three last-mentioned radicals may be partially or fully halogenated and/or may carry one to three substituents selected from the group consisting of C
1
-C
4
-alkoxy or hydroxyl,
is C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-hydroxyalkylthio, C
1
-C
6
-alkoxy-C
1
-C
6
-alkylthio,
is phenyl, naphthyl, heterocyclyl, phenoxy, phenylamino, diphenylamino, where the phenyl and heterocyclyl groups of the six last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-haloalkoxy,
is C(O)OR
5
, or C(O)N(R
6
)R
7
; and
R
4
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-hydroxyalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl,
is phenyl, naphthyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-haloalkoxy; where
R
5
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-hydroxyalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl,
is phenyl, naphthyl or heterocyclyl, where the three last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-haloalkoxy;
R
6
, R
7
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-hydroxyalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl,
are phenyl or naphthyl, where the two last-mentioned radicals for their part may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy and C
1
-C
4
-haloalkoxy; and
Hex is substituted (3-oxo-1-cyclohexen-2-yl)carbonyl of the formula IIa or is substituted (1,3-dioxo-2-cyclohexyl)methylidene of the formula IIb
 where the variables R
8
to R
14
are as defined below:
R
8
is hydroxyl, mercapto, halogen, OR
15
, SR
15
, SOR
16
, SO
2
R
16
, OSO
2
R
16
, P(O)R
17
R
18
, OP(O)R
17
R
18
, P(S)R
17
R
18
, OP(S)R
17
R
18
, NR
19
R
20
, ONR
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
9
, R
13
independently of one another are hydrogen, C
1
-C
4
-alkyl or C
1
-C
4
-alkoxycarbonyl;
R
10
, R
12
, R
14
independently of one another are hydrogen or C
1
-C
4
-alkyl;
R
11
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
10
and R
12
or R
12
and R
14
together form a n bond or a C
1
-C
5
-alkyl chain which may carry one, two or 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
10
and R
14
together form a C
1
-C
4
-alkyl chain which may carry one, two or 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
11
and R
12
together form a —O—(CH
2
)
p
—O—, —O—(CH
2
)
p
—S—, —S—(CH
2
)
p
—S—, —O—(CH2)
q
— or —S—(CH2)
q
— chain in which p is 2, 3, 4 or 5 and q is 2, 3, 4, 5 or 6, which may be substituted by one, two or three radicals from the following group: halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C4-alkoxycarbonyl;
or
R
11
and R
12
together with the carbon to which they are attached form a carbonyl group;
where
R
15
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
6
-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
-alkyny

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