3-Aminocarbonyl-substituted benzoylcyclohexanediones

Details 3-Aminocarbonyl-substituted benzoylcyclohexanediones 3-Aminocarbonyl-substituted benzoylcyclohexanediones

2002-09-10

2004-08-10

Berch, Mark L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S247000, C504S249000, C504S284000, C504S287000, C504S338000, C504S336000, C504S348000, C548S530000, C548S494000, C546S146000, C546S165000, C546S226000, C544S160000, C544S162000, C544S176000, C568S329000

Reexamination Certificate

active

06774086

ABSTRACT:

The invention relates to the technical field of the herbicides, in particular that of the herbicides from the benzoylcyclohexanedione group, for the selective control of broad-leaved weeds and grass weeds in crops of useful plants, in particular in rice crops.
It has already been disclosed in a variety of publications that certain benzoylcyclohexanediones have herbicidal properties. Thus, EP-A 0 319 075, WO 92/07837 and WO 96/22958 disclose benzoylcyclohexandiones with a haloalkoxy radical in the 3-position of the phenyl ring. WO 98/42648 mentions benzoylcyclohexanediones which have a variety of amino radicals attached to them in the 3-position. WO 99/10327 and WO 01/32636 describe herbicidally active benzoyl-cyclohexanediones with a heterocyclic substituent in the 3-position, which is bonded via an oxygen-carbon bridge.
However, the herbicidal activity of the compounds known from these publications is frequently insufficient. It is therefore an object of the present invention to provide herbicidally active compounds whose herbicidal properties are improved over the compounds disclosed in the prior art.
It has now been found that derivatives of benzoylcyclohexanediones whose phenyl ring has certain radicals from the aminocarbonylalkyl group attached to it in the 3-position—bonded to the phenyl ring via an atom selected from the group consisting of oxygen, sulfur and nitrogen—are particularly suitable as herbicides. The present invention therefore relates to compounds of the formula (I) or salts thereof
in which
X
1
is a divalent unit selected from the group consisting of O, S(O)
n
, N—H and N—R
2
;
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 radicals selected from the group consisting of halogen, cyano and nitro and by v radicals R
2
;
X
3
is oxygen or sulfur;
R
1a
, R
1b
, R
1c
independently of one another are hydrogen, mercapto, nitro, halogen, cyano, 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
, 1,2,4-triazol-1yl-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-cycloalkyl-(D)
p
, (C
1
-C
6
)-alkyl-cycloalkenyl-(D)
p
, each of which is substituted by v radicals selected from the group consisting of cyano, nitro and halogen;
D is oxygen or sulfur;
R
2
, R
3
independently of one another are hydrogen, (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, (C
3
-C
9
)-cycloalkyl, (C
3
-C
9
)-cycloalkenyl, (C
1
-C
6
)-alkyl-(C
3
-C
9
)-cycloalkyl, (C
1
-C
6
)-alkyl-(C
3
-C
9
)-cycloalkenyl, (C
2
-C
6
)-alkenyl-(C
3
-C
9
)-cycloalkyl, (C
2
-C
6
)-alkenyl-(C
3
-C
9
)-cycloalkenyl, (C
2
-C
6
)-alkynyl-(C
3
-C
9
)-cycloalkyl, (C
2
-C
6
)-alkynyl-(C
3
-C
9
)-cycloalkenyl, straight-chain or branched [O—C(R
6
)
2
]
w
-[O—C(R
6
)
2
]
x
-R
6
, (C
1
-C
6
)-alkylaryl, (C
2
-C
6
)-alkenylaryl, (C
2
-C
6
)-alkynylaryl, straight-chain or branched [O—C(R
6
)
2
]
w
-[O—C(R
6
)
2
]
x
-aryl, the abovementioned carbon-containing radicals being substituted by v radicals selected from the group consisting of cyano, nitro and halogen,
aryl, heterocyclyl or heteroaryl, each of which is substituted by v radicals selected from the group consisting of cyano, nitro, halogen, (C
1
-C
6
)-alkyl-(D)
p
and halo-(C
1
-C
6
)-alkyl-(D)
p
,
or
R
2
and R
3
together with the nitrogen atom to which they are bonded form a 5- or 6-membered, saturated, partially or fully unsaturated ring comprising m hetero atoms selected from the group consisting of oxygen and nitrogen, the 5- or 6-membered ring optionally being benzo-fused to a phenyl ring and being substituted by v radicals selected from the group consisting of cyano, nitro, halogen, (C
1
-C
6
)-alkyl-(D)
p
and halo-(C
1
-C
6
)-alkyl-(D)
p
and the fused phenyl ring being substituted by v radicals selected from the group consisting of cyano, nitro and halogen;
R
4
is OR
7
, (C
1
-C
4
)-alkylthio, halo-(C
1
-C
4
)-alkylthio, (C
2
-C
4
)-alkenylthio, halo-(C
2
-C
4
)-alkenylthio, (C
2
-C
4
)-alkynylthio, halo-(C
2
-C
4
)-alkynylthio, (C
1
-C
4
)-alkylsulfinyl, halo-(C
1
-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, halogen, cyano, cyanato, thiocyanato or phenylthio;
R
5
is hydrogen, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-yl, (C
1
-C
4
)-alkyl, (C
1
-C
8
)-cycloalkyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl, (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 chain being substituted by w methylene groups, or two radicals R
5
bonded to directly adjacent carbon atoms, together with the carbon atoms bearing them, 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 hydrogen, halogen, cyano or nitro, (C
1
-C
4
)-alkyl, halo-(C
1
-C
4
)-alkyl;
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, phenyl, benzoyl or phenylsulfonyl, the three last-mentioned groups being substituted by v radicals selected from the group consisting of (C
1
-C
4
)-alkyl, halo-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, halo-(C
1
-C
4
)-alkoxy, halogen, cyano and nitro;
Y is a divalent unit selected from the group consisting of O, S, N—H, N—(C
1
-C
6
)-alkyl, CHR
5
and C(R
5
)
2
;
Z is a direct bond or a divalent unit selected from the group consisting of O, S, SO, SO
2
, N—H, N-alkyl, CHR
6
or C(R
6
)
2
;
m and n in each case independently of one another are 0, 1 or 2;
p is independently 0 or 1;
v is independently 0, 1, 2 or 3;
w and x in each case independently of one another are 0, 1, 2, 3 or 4, with the proviso that w and x are not simultaneously zero.
In the event that R
4
is OH, the compounds of the formula (I) according to the invention can exist in different tautomeric structures, depending on the external conditions such as solvent and pH. Depending on the nature of the substituents, the compounds of the formula (I) contain an acidic proton, which can be removed for example by reaction with a base. Examples of suitable bases are hydrides, hydroxides and carbonates of alkali and alkaline earth metals, such as lithium, sodium, potassium, magnesium and calcium, and also ammonia and organic amines such as triethylamine and pyridine. The invention likewise relates to such salts.
In formula (I) and all subsequent formulae, alkyl radicals with more than two carbon atoms can be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3-dimethylbutyl. Likewise, the carbon chain X
2
can be straight-chain or branched, depending on the number of carbon atoms which it contains. The radicals bonded thereto can be in any desired position of this chain.
If a

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