Herbicidally active benzoylcyclohexanediones

Details Herbicidally active benzoylcyclohexanediones Herbicidally active benzoylcyclohexanediones

2001-08-30

2004-12-07

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S223000, C504S236000, C504S237000, C504S238000, C504S254000, C504S269000, C504S271000, C504S287000, C504S288000, C504S289000, C504S292000, C504S299000, C504S310000, C504S326000, C504S348000, C544S003000, C544S063000, C544S238000, C544S239000, C544S240000, C544S241000, C546S288000, C546S296000, C546S297000, C546S298000, C548S213000, C548S243000, C548S366700, C548S367100, C548S369400, C548S539000, C549S028000, C549S064000, C549S294000, C549S318000, C549S322000, C549S417000, C549S477000

Reexamination Certificate

active

06828276

ABSTRACT:

The invention relates to the technical field of the herbicides, in particular that of the herbicides for selectively controlling broad-leaved weeds and grass weeds in crops of useful plants.
It has already been disclosed in various publications that certain benzoylcyclohexanediones, including those which are substituted in the 3-position of the phenyl ring, for example by a cyclic radical, have herbicidal properties. WO 99/10327 discloses benzoylcyclohexanediones which have attached to them in the 3-position of the phenyl ring a heterocyclic radical containing at least one nitrogen atom and bonded via a chain of carbon atoms. WO 00/21924 mentions benzoylcyclohexanediones which have attached to them in the 3-position of the phenyl ring a heterocyclic or carbocyclic radical which is bonded via a chain of carbon atoms.
However, the application of the compounds disclosed in these publications frequently entails disadvantages in practice. Thus, the herbicidal activity of the known compound is not always sufficient, or, when the herbicidal activity is sufficient, undesired crop plant damage is observed. It was therefore an object of the present invention to provide herbicidally active compounds which have improved herbicidal properties over the compounds known from the prior art.
It has now been found that benzoylcyclohexanediones which have attached to them in the 3-position of the phenyl ring certain cyclic radicals which are bonded via an oxygen, nitrogen or sulfur atom are particularly suitable as herbicides. Subject matter of the present invention are therefore compounds of the formula (I) or their salts
in which
X
1
is a divalent unit selected from the group consisting of O, S(O)
n
, NH, N[L
p
-R
3
];
X
2
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 halogen atoms;
C
1
(C
2
)
q
(C
3
)
o
is a mono-, bi- or tricyclic radical, where
a) the rings C
1
, C
2
and C
3
are in each case a 3- to 8-membered, saturated or partially saturated ring selected from the group consisting of cycloalkyl, cycloalkenyl, oxiranyl and oxetanyl,
b) the rings C
1
, C
2
and C
3
are in each case linked to each other via one or two joint atoms;
R
1
and R
2
independently of one another are hydrogen, mercapto, nitro, cyano, halogen, thiocyanato, (C
1
-C
6
)-alkyl-CO—O, (C
1
-C
6
)-alkyl-S(O)
n
—O, (C
1
-C
6
)-alkyl-S(O)
n
, di-(C
1
-C
6
)-alkyl-NH—SO
2
, (C
1
-C
6
)-alkyl-SO
2
—NH, (C
1
-C
6
)-alkyl-NH—CO, (C
1
-C
6
)-alkyl—SO
2
—[(C
1
-C
6
)-alkyl]amino, (C
1
-C
6
)-alkyl-CO—((C
1
-C
6
)-alkyl)amino, 1,2,4-triazol-1-yl, (C
1
-C
6
)-alkyl-O—CH
2
, (C
1
-C
6
)-alkyl-S(O)
n
—CH
2
, (C
1
-C
6
)-alkyl-NH—CH
2
, [(C
1
-C
6
)-alkyl]
2
N—CH
2
, 1,2,4-triazol-1-yl-CH
2
, or are (C
1
-C
6
)-alkyl-(D)
p
, (C
2
-C
6
)-alkenyl-(D)
p
, (C
2
-C
6
)-alkynyl-(D)
p
, (C
3
-C
9
)-cycloalkyl-(D)
p
, (C
3
-C
9
)-cycloalkenyl-(D)
p
, (C
1
-C
6
)-alkyl-(C
3
-C
9
)-cycloalkyl-(D)
p
or (C
1
-C
6
)-alkyl-(C
3
-C
9
)-cycloalkenyl-(D)
p
, each of which is substituted by v radicals selected from the group consisting of cyano, nitro and halogen;
R
3
is hydrogen, hydroxyl, halogen, mercapto, amino, nitro, a carbon-containing radical or, if p in X
1
is zero, R
3
is oxo, NR
8
, N—OR
8
or N—NR
8
R
9
;
D is oxygen or sulfur;
L is in each case straight-chain or branched A
p
-[C(R
6
)
2
]
w
-[A
p
-C(R
6
)
2
]
x
-A
p
or A
p
-M-A
p
;
with the proviso that 2 or 3 of the variable terms p, w and x shall not simultaneously be zero;
A is a divalent unit selected from the group consisting of O, S(O)
n
, NH, N—(C
1
-C
6
)-alkyl, N—(C
2
-C
6
)-alkenyl and N—(C
2
-C
6
)-alkynyl;
M is (C
1
-C
6
)-alkylene, (C
2
-C
6
)-alkenylene or (C
2
-C
6
)-alkynylene, each of which is substituted by w radicals R
6
;
R
4
is OR
7
, (C
1
-C
4
)-alkylthio, halo-(C
1
-C
4
)-alkylthio, (C
1
-C
4
)-alkenylthio, halo-(C
2
-C
4
)-alkenylthio, (C
2
-C
4
)-alkynylthio, halo-(C
2
-C
4
)-alkynylthio, (C
2
-C
4
)-alkylsulfinyl, halo-(C
2
-C
4
)-alkylsulfinyl, (C
2
-C
4
)-alkenylsulfinyl, halo-(C
2
-C
4
)-alkenylsulfinyl, (C
2
-C
4
)-alkynylsulfinyl, halo-(C
2
-C
4
)-alkynylsulfinyl, (C
1
-C
4
)-alkylsulfonyl, halo-(C
1
-C
4
)-alkylsulfonyl, (C
2
-C
4
)-alkenylsulfonyl, halo-(C
2
-C
4
)-alkenylsulfonyl, (C
2
-C
4
)-alkynylsulfonyl, halo-(C
2
-C
4
)-alkynylsulfonyl, cyano, cyanato, thiocyanato, halogen or phenylthio;
R
5
is hydrogen, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-yl, (C
1
-C
4
)-alkyl, (C
3
-C
8
)-cycloalkyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylcarbonyl, (C
1
-C
4
)-alkoxycarbonyl, (C
1
-C
4
)-alkylthio, phenyl, the eight last-mentioned groups being substituted by v radicals selected from the group consisting of halogen, (C
1
-C
4
)-alkylthio and (C
1
-C
4
)-alkoxy, or two radicals R
5
bonded 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, this group being substituted by w methyl groups, or two radicals R
5
bonded to directly adjacent carbon atoms, together with the carbon atoms to which they are attached, form a 3- to 6-membered ring which is substituted by w radicals selected from the group consisting of halogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylthio and (C
1
-C
4
)-alkoxy;
R
6
is (C
1
-C
4
)-alkyl, halogen, cyano or nitro;
R
7
is hydrogen, (C
1
-C
4
)-alkyl, halo-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl, formyl, (C
1
-C
4
)-alkylcarbonyl, (C
1
-C
4
)-alkoxycarbonyl, (C
1
-C
4
)-alkylaminocarbonyl di-(C
1
-C
4
)-alkylaminocarbonyl, (C
1
-C
4
)-alkylsulfonyl, halo-(C
1
-C
4
)-alkylsulfonyl, benzoyl or phenylsulfonyl, the two last-mentioned groups being substituted by v radicals selected from the group consisting of (C
1
-C
4
)-alkyl, halo-(C
1
-l
4
)-alkyl, (C
1
-C
4
)-alkoxy, halo-(C
1
-C
4
)-alkoxy, halogen, cyano and nitro;
R
8
is hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, (C
2
-C
4
)-alkenyl, (C
2
-C
4
)-alkynyl, (C
3
-C
8
)-cycloalkyl, aryl, aryl-(C
1
-C
6
)-alkyl, heteroaryl, heterocyclyl, halo-(C
1
-C
4
)-alkyl;
R
9
is hydrogen, (C
1
-C
4
)-alkyl, (C
2
-C
4
)-alkenyl, (C
2
-C
4
)-alkynyl, (C
3
-C
9
)-cycloalkyl, aryl, aryl-(C
1
-C
6
)-alkyl, heteroaryl, heterocyclyl, halo-(C
1
-C
4
)-alkyl, or, if R
8
and R
9
are bonded to one atom or to two directly adjacent atoms, they together with the atoms to which they are bonded form a saturated, partially or fully unsaturated five- to six-membered ring which contains p hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur;
Y is a divalent unit selected from the group consisting of O, S, N—H, N—(C
1
-C
4
)-alkyl, CHR
5
and C(R
5
)
2
;
Z is a divalent unit selected from the group consisting of O, S, SO, SO
2
, N—H, N—(C
1
-C
4
)-alkyl, CHR
5
and C(R
5
)
2
;
m and n are each 0, 1 or 2;
o, p and q are each 0 or 1;
w and x are each 0, 1, 2, 3 or 4;
v is 0, 1, 2 or 3.
Depending on external conditions such as solvent and pH, a large number of compounds of the formula (I) according to the invention can occur in different tautomeric structures. Depending on the nature of the substituents, the compounds of the formula (I) contain an acidic proton, which can be removed by reaction with a base. Examples of suitable bases are hydrides, hydroxides and carbonates of lithium, sodium, potassium, magnesium and calcium, and ammonia and organic amines such as triethylamine and pyridine. Such salts are also subject matter of the invention.
In all of the formulae mentioned hereinbelow, the substituents and symbols, unless otherwise defined, have the same meaning as described under formula (I).
In formula (I) and all subsequent formulae, chain-like carbon-containing radicals such as alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding radicals which are unsaturated and/or substituted in the carbon skeleton, such as alkenyl and alkynyl, can in each case be straight-chain or branched. Unless specifically indicated, the lower carbon skeletons, for ex

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