Herbicidal compounds

Details Herbicidal compounds Herbicidal compounds

1999-05-27

2001-09-18

Gerstl, Robert (Department: 1613)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C568S367000

Reexamination Certificate

active

06291400

ABSTRACT:

The present invention relates to certain herbicidally active substituted cyclic diones, to processes for their preparation and to compositions containing them.
Herbicidal compounds containing a cyclohexane dione coupled to an aryl group are described and claimed for example in EP-A-90262, EP-A-137,963, EP-A-135,191 and EP-A-186119.
According to the present invention there is provided a compound of formula (I):
or a salt, enamine or the like, acylate, sulphonate, carbamate or ether derivative thereof; wherein X, X
1
and X
2
are independently oxygen or sulphur; R
1
is an optionally substituted heterocyclic or cycloalkyl group; and Y is optionally substituted C
2
-C
4
alkylene group which is optionally interposed by an oxygen atom, a group
a group
or an optionally mono-substituted nitrogen atom, wherein p is 0, 1 or 2, s is 0 or 1 and R
b
is alkyl or alkoxy; provided that when X, X
1
and X
2
are oxygen, R
1
is not pyridyl or pyrimidinyl.
Compounds of formula (I) can exist in a number of tautomeric forms, for example:
wherein R
1
, X, X
1
, X
2
and Y are as defined in relation to formula (I). Further tautomers exist when Y contains a hydrogen substituent on a carbon atom adjacent to the carbon bearing X
1
or X
2
. It is intended that all such forms are included within the scope of the invention.
When the compound contains a free hydroxy or thiol group in this way, it may be derivatised to form salts, in particular agriculturally acceptable salts, enamines or the like, acylates, sulphonates, carbamates or ethers.
Suitable agriculturally acceptable salts include salts such as sodium, potassium, calcium and ammonium salts.
Examples of ammonium salts include salts with ions of formula N
+
R
c
R
d
R
e
R
f
where R
c
, R
d
, R
e
and R
f
are independently selected from hydrogen and C
1-10
alkyl optionally substituted by, for example, hydroxy. Suitably when any of R
c
, R
d
, R
e
or R
f
are optionally substituted alkyl, they contain from 1 to 4 carbon atoms.
Suitable acylate or ether derivatives are compounds wherein the OH moiety has been converted to a group of formula —OCOR
2
or —OR
2
respectively wherein R
2
is optionally substituted alkyl having for example from 1 to 6 carbon atoms, or aryl such as phenyl.
Suitable carbamate derivatives are compounds wherein the OH moiety has been converted to a group
wherein R
3
and R
4
are independently hydrogen or a group R
2
as defined above.
Preferably X, X
1
and X
2
are oxygen.
As used herein the term “enamine or the like” refers to derivatives where one of X or X
1
is oxygen and the other is replaced by NR
3
R
4
, halo such as fluoro or SR
2
.
These derivatives can be prepared by conventional methods.
Suitable heterocyclic groups R
1
include mono- or fused bicyclo-heterocyclic rings which may be aromatic or non-aromatic. Suitably R
1
includes up to ten ring atoms up to five preferably three of which may be selected from oxygen, nitrogen and sulphur.
When R
1
is a monocyclic ring, it is suitably a heteroaryl group having up to 7 ring atoms up to 3 of which are selected from oxygen, nitrogen and sulphur. As used here in the term “heteroaryl” means aromatic heterocyclic.
When R
1
is a fused bicyclic ring, one or both of the rings may contain heteroatoms and it may be bonded to the group
by way of either of these rings.
Examples of such heterocyclic groups including furyl, thienyl, pyrrolyl, pyrazolyl, pyridyl, pyrimidinyl, imidazoyl, triazolyl, dithiol, oxathiol, isoxazolyl, oxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiodiazolyl, oxatriazolyl, dioxazolyl, oxathiazolyl, oxathiol, dioxinyl, pyridazinyl, pyrazinyl, piperazinyl, priazinyl, oxazinyl, isoxazinyl, oxathiazinyl, morphlinyl, azepinyl, oxepinyl, thiepinyl, diazepinyl, benzofuranyl, isobenzofuranyl, benzothienyl, isobenzothienyl, thionaphthalenyl, isothionaphthalenyl, indolyl, isoindolyl, indazolyl, indoleninyl, isobenzazolyl, pyranopyrrolyl, isoindazolyl, indoxazinyl, benzoxazolyl, benzopyranyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, pyridopyridinyl, pyranyl, thiopyranyl, chromenyl, thiachromenyl, benzoxazinyl, benzisoxazinyl and purine.
Particular examples of heterocyclic groups R
1
include furyl, thiazolyl, thienyl, benzoxazolyl, pyrazolyl, pyridazinyl, pyrazinyl, benzoxazolyl.
These heterocycles may be linked either through a carbon atom or when possible through a nitrogen atom.
Suitable cycloalkyl groups R
1
contain up to 10 ring carbon atoms, preferably up to 7 ring atoms.
Suitable optional substituents for the groups R
1
and R
8
include one or more groups selected from oxo, mercapto, halo, such as fluoro, chloro, bromo or iodo, nitro, cyano, amino, mono or dialkylamino, amido, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl such as trifluoromethyl, haloalkoxy such as trifluoromethoxy, optionally substituted aryl such as phenyl or naphthyl, hydroxy, alkoxy, alkoxycarbonyl, alkylcarbonyl, mono- or dialkylcarbamoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, sulphonamido, alkylcarbonyloxy, alkylcarbonylamino or heterocyclyl such as pyridyl and thienyl.
The substituents may be attached to a carbon and/or nitrogen atom of the group R
1
.
In the above-mentioned list of substituents, the alkyl, alkenyl or alkynyl groups or moieties preferably contain from 1 to 6 carbon atoms. Suitable optional substituents for the aryl groups include halo such as fluoro, chloro or bromo, C
1-6
alkyl or C
1-6
alkoxy.
In a preferred embodiment, R
1
is a 6-membered heteroaryl ring for example from one or two nitrogen atoms such as pyridyl, pyrimidinyl, pyridazinyl or pyrazinyl.
In another preferred embodiment, R
1
is a five membered heteroaryl group or comprises a five-membered heteroaryl group.
For example, R
1
is selected from groups of formula:
wherein R
5
is hydrogen or C
1
-C
4
alkyl, preferably C
1
-C
2
alkyl or optionally substituted aryl such as phenyl;
R
6
, R
7
and R
8
independently are (1) hydrogen; (2) halogen, preferably chlorine, fluorine or bromine; (3) C
1
-C
4
alkyl, preferably methyl; (4) haloalkoxy, preferably OCF
3
; (5) C
1
-C
4
alkoxy, preferably methoxy; (6) cyano; (7) nitro; (8) C
1
-C
4
haloalkyl, preferably trifluoromethyl; (9) R
9
SOn— wherein n is the integer 0, 1 or 2, preferably 2; and R
9
is
(a) C
1
-C
4
alkyl, preferably methyl;
(b) C
1
-C
4
alkyl substituted with halogen, cyano, C
1
-C
2
alkoxy or C
1
-C
2
alkylthio, preferably chloromethyl, difluoromethyl, trifluoromethyl or cyanomethyl;
(c) phenyl; or
(d) benzyl;
(10) —NR
10
R
11
wherein R
10
and R
11
independently are hydrogen or C
1
-C
4
alkyl; (11) R
12
C(O)— wherein R
12
is C
1
-C
4
alkyl or C
1
-C
4
alkoxy; (12) —SO
2
NR
10
R
11
wherein R
10
and R
11
are as defined above; or (13) —N(R
10
)C(O)R
11
wherein R
10
and R
11
are as defined above.
In particular R
1
is a group of formula:
wherein R
5
and R
6
are as defined above.
In particular R
5
is C
1-6
alkyl which may be straight or branched or optionally substituted phenyl, such as phenyl, p-chlorophenyl, p-methoxyphenyl or p-methylphenyl.
Preferred groups R
6
are haloalkyl in particular trifluoromethyl.
In a further preferred embodiment R
1
is a bicyclic group of formula
wherein R
6
, R
7
and R
8
are as defined above;
One of R
12
or R
13
is —N═ and the other is C(R
14
) wherein R
14
is hydrogen, halogen, such as chlorine, fluorine or bromine; C
1
-C
4
alkyl, such as methyl; OCF
3
; C
1
-C
4
alkoxy, such as methoxy; cyano; nitro; C
1
-C
4
haloalkyl, such as trifluoromethyl; R
15
SOm wherein m is the integer 0, 1 or 2, preferably 2; and R
15
is C
1
-C
4
alkyl, such as methyl.
In addition R
1
may be a bicyclic group of sub formula
wherein Z is a five or six membered saturated or unsaturated fused ring containing up to three heteroatoms selected from oxygen, sulphur and nitrogen. Preferably the ring Z contains two oxygen atoms or an oxygen or sulphur and a nitrogen atom. Thus examples of the group R
1
include
where R
6
is as defined above.
Suitable optional substituents for the group Y include those listed above

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