Benzoylcyclohexanediones and benzoylpyrazoles, their...

Details Benzoylcyclohexanediones and benzoylpyrazoles, their... Benzoylcyclohexanediones and benzoylpyrazoles, their...

2000-11-02

2002-09-10

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S139000, C504S244000, C504S282000, C546S276100, C548S364100, C548S365700, C548S110000, C548S128000, C548S131000, C548S143000, C548S203000, C548S204000, C548S214000, C548S247000, C548S240000, C548S255000, C548S266200, C548S312400, C544S096000, C544S182000

Reexamination Certificate

active

06448201

ABSTRACT:

DESCRIPTION
Benzoylcyclohexanediones and benzoylpyrazoles, their preparation and their use as herbicides and plant growth regulators.
The invention relates to the technical field of the herbicides and plant growth regulators, in particular that of the herbicides for the selective control of broad-leaved weeds and grass weeds in crops of useful plants.
It is already known from various publications that certain benzoyl derivatives, including those which have, in the 3-position of their phenyl ring, for example a heterocyclic radical which is bound directly or via a monoatomic or polyatomic bridge, have herbicidal properties. Thus, WO 99/07697 describes benzoylpyrazoles which have attached to them in the abovementioned position an optionally substituted heterocyclic radical which is bound via a carbon atom chain. WO 99/10327 and WO 99/10328 disclose benzoylcyclohexanediones and benzoylpyrazoles, respectively, which have attached to them an optionally substituted heterocyclic radical which is bound via a chain of carbon atoms and a hetero atom.
However, the use of the benzoyl derivatives known from these publications frequently entails disadvantages in practice. Thus, the herbicidal or plant-growth-regulatory activity of the known compounds is not always sufficient, or, if the herbicidal activity is sufficient, then undesired damage to the useful plants is observed.
The object of the present invention is to provide compounds which have a herbicidal and plant-growth-regulatory action and- which overcome the disadvantages known from the prior art.
The present invention therefore relates to benzoyl derivatives of the formula (I) which are specifically substituted in the 3-position of the phenyl ring
in which
Q is a radical of the formula (Q1) which is linked in the 2-position or a radical of the formula (Q2) which is linked in the 4-position
X is a straight-chain or branched (C
1
-C
6
)alkylene, (C
2
-C
6
)-alkenylene or (C
2
-C
6
)-alkynylene chain, which is substituted by w radicals selected from the group consisting of OR
3a
, OCOR
3a
, halogen, OCONHR
3a
, OSO
2
R
3a
, (C
1
-C
6
)alkyl, (C
2
-C
6
)alkenyl, (C
2
-C
6
)alkynyl, phenyl and phenyl-(C
1
-C
6
)-alkyl, and which is interrupted by a hetero atom selected from the group consisting of oxygen and sulfur or which has this hetero atom attached to one of its chain ends, the abovementioned alkyl, alkenyl, alkynyl and phenyl radicals optionally being substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, (C
1
-C
4
)-alkylamino, (C
1
-C
4
)-dialkylamino, (C
1
-C
4
)-alkoxycarbonyl, (C
1
-C
4
)-alkylcarbonyl, (C
1
-C
4
)-alkoxycarbonyloxy, (C
1
-C
4
)-alkyl, halo-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylthio, halo-(C
1
-C
4
)-alkylthio, (C
1
-C
4
)-alkoxy, halo-(C
1
-C
4
)-alkoxy;
Het is heterocyclyl or heteroaryl containing, as ring atom, at least one nitrogen atom and optionally additionally one, two or three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur;
R
1
and R
2
independently of one another are hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkoxy-(C
1
-C
6
)-alkyl, halo-(C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, OS(O)
n
R
10
, (C
1
-C
6
)-alkyl-A, (C
2
-C
6
)-alkenyl-A, (C
2
-C
6
)-alkynyl-A, (C
1
-C
6
)-alkoxy-(C
1
-C
6
)-alkyl-A, or are (C
2
-C
6
)-alkenyloxy-(C
1
-C
6
)-alkyl-(A)
p
, (C
2
-C
6
)-alkynyloxy-(C
1
-C
6
)-alkyl-(A)
p
, (C
3
-C
9
)-cycloalkyl-(A)
p
, (C
3
-C
9
)-cycloalkenyl-(A)
p
, (C
1
-C
6
)-alkyl-(C
3
-C
9
)-cycloalkyl-(A)
p
, (C
1
-C
6
)-alkyl-(C
3
-C
9
)-cycloalkyl-(C
1
-C
6
)-alkyl-(A)
p
, (C
1
-C
6
)-alkyl-(C
3
-C
9
)-cycloalkenyl-(A)
p
, (C
1
-C
6
)-alkyl-(C
3
-C
9
)-cycloalkenyl-(C
1
-C
6
)-alkyl-(A)
p
, (C
2
-C
6
)-alkenyl-(C
3
-C
9
)-cycloalkyl-(A)
p
, (C
2
-C
6
)-alkenyl-(C
3
-C
9
)-cycloalkyl-(C
1
-C
6
)-alkyl-(A)
p
, (C
2
-C
6
)-alkenyl-(C
3
-C
9
)-cycloalkenyl-(A)
p
, (C
2
-C
6
)-alkenyl-(C
3
-C
9
)-cycloalkenyl-(C
1
-C
6
)-alkyl-(A)
p
, (C
2
-C
6
)-alkynyl-(C
3
-C
9
)-cycloalkyl-(A)
p
, (C
2
-C
6
)-alkynyl-(C
3
-C
9
)-cycloalkyl-(C
1
-C
6
)-alkyl-(A)
p
, (C
2
-C
6
)-alkynyl-(C
3
-C
9
)-cycloalkyenyl-(A)
p
, (C
2
-C
6
)-alkynyl-(C
3
-C
6
)-cycloalkenyl-(C
1
-C
6
)-alkyl-(A)
p
, OR
10
, OCOR
10
, S(O)
n
R
10
, SO
2
N(R
10
)
2
, NR
10
SO
2
R
10
or NR
10
COR
10
, each of which is substituted by m radicals selected from the group consisting of cyano and nitro and w radicals selected from the halogen group;
R
3
is hydrogen, hydroxyl, halogen, mercapto, amino, cyano, nitro, formyl, or is (C
1
-C
4
)-alkylamino, (C
1
-C
4
)-dialkylamino, (C
1
-C
4
)-alkoxycarbonyl, (C
1
-C
4
)-alkylcarbonyl, (C
1
-C
4
)-alkylcarbonyloxy, (C
1
-C
4
)-alkyl, halo(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylthio, halo(C
1
-C
4
)-alkylthio, (C
1
-C
4
)-alkoxy or halo(C
1
-C
4
)-alkoxy, each of which is substituted by m radicals selected from the group consisting of cyano, formyl, nitro, (C
1
-C
4
)-alkylamino, (C
1
-C
4
)-dialkylamino, (C
1
-C
4
)-alkoxycarbonyl, (C
1
-C
4
)-alkylcarbonyl, (C
1
-C
4
)-alkylcarbonyloxy, (C
1
-C
4
)-alkyl, (C
2
-C
4
)-alkenyl, (C
2
-C
4
)-alkynyl, halo(C
1
-C
4
)-alkyl, (C
2
-C
4
)-haloalkenyl, (C
2
-C
4
)-haloalkynyl, (C
1
-C
4
)-alkylthio, halo(C
1
-C
4
)-alkylthio, (C
1
-C
4
)-alkoxy and halo(C
1
-C
4
)-alkoxy;
R
3a
is hydrogen, (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, phenyl, phenyl-(C
1
-C
6
)-alkyl, it being possible for the five last-mentioned radicals to be substituted in their nonaromatic moiety by w radicals selected from the group consisting of hydroxyl, halogen, mercapto, amino, cyano, nitro, formyl, (C
1
-C
4
)-alkylamino, (C
1
-C
4
)-dialkylamino, (C
1
-C
4
)-alkoxycarbonyl, (C
1
-C
4
)-alkylcarbonyl, halo-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylthio, halo-(C
1
-C
4
)-alkylthio, (C
1
-C
4
)-alkoxy and halo-(C
1
-C
4
)alkoxy;
R
4
is straight-chain or branched [C(R
11
)
2
]
m
-(A)
p
-[C(R
11
)
2
]
m
-R
12
;
A is oxygen or sulfur;
R
5
is OR
16
, (C
1
-C
6
)-alkylthio, halo-(C
1
-C
6
)-alkylthio, (C
2
-C
6
)-alkenylthio, halo-(C
2
-C
6
)-alkenylthio, (C
2
-C
6
)-alkynylthio, halo-(C
2
-C
6
)-alkynylthio, (C
1
-C
6
)-alkylsulfinyl, halo-(C
1
-C
6
)-alkylsulfinyl, (C
2
-C
6
)-alkenylsulfinyl, halo-(C
2
-C
6
)-alkenylsulfinyl, (C
2
-C
6
)-alkynylsulfinyl, halo-(C
2
-C
6
)-alkynylsulfinyl, (C
1
-C
6
)-alkylsulfonyl, halo-(C
1
-C
6
)-alkylsulfonyl, (C
2
-C
6
)-alkenylsulfonyl, halo-(C
2
-C
6
)-alkenylsulfonyl, (C
2
-C
6
)-alkynylsulfonyl, halo-(C
2
-C
6
)-alkynylsulfonyl, cyano, cyanato, thiocyanato or halogen;
R
6
is hydrogen, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-yl, or is (C
1
-C
6
)-alkyl, (C
3
-C
6
)-cycloalkyl, (C
1
-C
6
)-alkoxy, (C
1
-C
6
)-alkylcarbonyl, (C
1
-C
6
)-alkoxy-(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkoxycarbonyl, (C
1
-C
6
)-alkylthio or phenyl, each of which is substituted by w radicals selected from the group consisting of halogen, (C
1
-C
6
)-alkylthio and (C
1
-C
6
)-alkoxy, or two radicals R
6
bound to a joint carbon atom form a chain selected from the group consisting of OCH
2
CH
2
O, OCH
2
CH
2
CH
2
O, SCH
2
CH
2
S and SCH
2
CH
2
CH
2
S which is optionally substituted by one to four methyl groups;
R
7
is hydrogen, (C
1
-C
6
)-alkyl or (C
1
-C
6
)-haloalkyl;
R
8
is (C
1
-C
6
)-alkyl, halo-(C
1
-C
6
)-alkyl, or is phenyl which is optionally substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, (C
1
-C
4
)-alkyl, halo-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy and halo-(C
1
-C
4
)-alkoxy;
R
9
is hydrogen, (C
1
-C
6
)-alkyl, halo-(C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkylcarbonyl, halo-(C
1
-C
6
)-alkylcarbonyl, (C
1
-C
6
)-alkoxycarbonyl, (C
1
-C
6
)-alkylsulfonyl, halo-(C
1
-C
6
)-alkylsulfonyl, or is benzoyl, benzoylmethyl, phenoxycarbonyl or phenylsulfonyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, (C
1
-C
4
)-alkyl, halo-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy and halo-(C
1
-C
4
)-alkoxy;
R
10
is hydrogen, or is (C
1
-C
6

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