Heterocyclyl-substituted benzoylcyclohexandiones, their...

Details Heterocyclyl-substituted benzoylcyclohexandiones, their... Heterocyclyl-substituted benzoylcyclohexandiones, their...

2001-08-30

2004-03-09

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S242000

Reexamination Certificate

active

06703348

ABSTRACT:

The invention relates to the technical field of the herbicides, 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 benzoylcyclohexanediones, including those which are substituted in the 3-position of the phenyl ring, for example by a heterocyclic radical, have herbicidal properties. Such benzoylcyclohexane diones are particularly suitable for controlling harmful plants in maize. WO 96/26200 describes benzoylcyclohexanediones which have a 5- or 6-membered heterocycle attached in the 3-position of the phenyl ring. This heterocycle can be saturated or unsaturated and substituted or unsubstituted. Moreover, this heterocycle may form a bicyclic system together with a fused second ring.
However, the application of the benzoylcyclohexanediones known from these publications frequently entails disadvantages in practice. Thus, the herbicidal activity of the known compound is not always sufficient, or else, while the herbicidal activity is sufficient, undesirable damage is observed on the crop plants. In particular, the harmful Setaria species, which are considered to be a particular problem in the United States, which constitute the world's largest market for maize, are only controlled insufficiently by the known benzoylcyclohexanediones. The object of the present invention was therefore to provide herbicidally active compounds with herbicidal properties which are improved over those of the prior-art compounds, in particular for use in maize crops.
It has now been found that benzoylcyclohexanediones which have certain radicals selected from the group of the oligocyclic radicals attached in the 3-position of the phenyl ring are particularly well suited as herbicides. A subject of the present invention is therefore compounds of the formula (I) or their salts
in which
R
1
is halogen, (C
1
-C
4
)-alkyl, halogen-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylsulfenyl, (C
1
-C
4
)-alkylsulfinyl, (C
1
-C
4
)-alkylsulfonyl or nitro;
R
2
is a radical AB(C)
q
(D)
o
which is linked to the benzoyl moiety via A;
AB(C)
q
(D)
o
is a bi-, tri- or tetracyclic radical, where
a) A, B, C and D are in each case a 3- to 8-membered, saturated, partially saturated, unsaturated or aromatic ring containing 1 to 4 hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur,
b) the rings A, B, C and D are in each case substituted by v substituents selected from the group consisting of R
6
, halogen, cyano, nitro, hydroxyl, oxo, (C
1
-C
4
)-alkyl, halogen-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, halogen-(C
1
-C
4
)-alkoxy and di-(C
1
-C
4
)-alkylamino,
c) two rings A, B, C and D are linked to each other via two joint atoms,
d) B is not the benzo group when A contains at least one hetero atom;
R
3
is halogen, halogen-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylsulfinyl, (C
1
-C
4
)-alkylsulfinyl, (C
1
-C
4
)-alkylsulfonyl or nitro;
R
4
is OR
7
, (C
1
-C
4
)-alkylthio, halogen-(C
1
-C
4
)-alkylthio, (C
1
-C
4
)-alkenylthio, halogen-(C
2
-C
4
)-alkenylthio, (C
2
-C
4
)-alkynylthio, halogen-(C
2
-C
4
)-alkynylthio, (C
2
-C
4
)-alkylsulfinyl, halogen-(C
2
-C
4
)-alkylsulfinyl, (C
2
-C
4
)-alkenylsulfinyl, halogen-(C
2
-C
4
)-alkenylsulfinyl, (C
2
-C
4
)-alkynylsulfinyl, halogen-(C
2
-C
4
)-alkynylsulfinyl, (C
1
-C
4
)-alkylsulfonyl, halogen-(C
1
-C
4
)-alkylsulfonyl, (C
2
-C
4
)-alkenylsulfonyl, halogen-(C
2
-C
4
)-alkenylsulfonyl, (C
2
-C
4
)-alkynylsulfonyl, halogen-(C
2
-C
4
)-alkynylsulfonyl, cyano, cyanato, thiocyanato, halogen, or is phenylthio which is substituted by v radicals selected from the group consisting of halogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, halogen-(C
1
-C
4
)-alkyl, halogen-(C
1
-C
4
)-alkoxy, cyano and nitro;
R
5
is tetrahydropyranyl-3, tetrahydropyranyl-4, tetrahydrothiopyranyl-3, (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, these being substituted by w methyl groups, or two radicals R
5
bonded to directly adjacent carbon atoms form a bond or, together with the carbon atoms to which they are attached, form a 3- to 6-membered ring 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 straight-chain or branched [C(R
8
)
2
]
m
-(G)
p
-[C(R
8
)
2
]
m
-R
9
;
R
7
is hydrogen, (C
1
-C
4
)-alkyl, halogen-(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, halogen-(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, halogen-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, halogen-(C
1
-C
4
)-alkoxy, halogen, cyano and nitro;
R
8
is hydrogen, (C
1
-C
4
)-alkyl or halogen;
R
9
is OR
13
, SR
13
, SOR
13
, SO
2
R
13
, CO
2
R
14
, CONR
14
R
15
, N(R
14
)COR
15
, N(R
14
)SO
2
R
15
, P(O)R
14
R
15
, halogen, cyano, nitro, (C
3
-C
8
)-cycloalkyl, (C
3
-C
8
)-cycloalkyl, aryl, 5- or 6-membered heterocyclyl or heteroaryl with in each case one to four hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, it being possible for these five abovementioned radicals to be substituted by v substituents selected from the group consisting of halogen, cyano, formyl, nitro, (C
1
-C
4
)-alkyl, halogen-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, halogen-(C
1
-C
4
)-alkoxy, (C
1
-C
4
)-alkylthio, halogen-(C
1
-C
4
)-alkylthio and R
10
, or is a radical of the formula Va to Vt:
R
10
is [(C
1
-C
4
)-alkylene-O—(C
1
-C
4
)-alkylene]
n
-O—(C
1
-C
4
)-alkyl, or is (C
1
-C
4
)-alkyl, (C
2
-C
4
)-alkenyl or (C
2
-C
4
)-alkynyl, each of which is substituted by v halogen atoms;
R
11
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, halogen-(C
1
-C
4
)-alkyl;
R
12
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, halogen-(C
1
-C
4
)-alkyl, or, if R
11
and R
12
are bonded to one atom or to two directly adjacent atoms, they form together with the atoms binding them 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;
R
13
is R
7
, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, (C
3
-C
8
)-cycloalkyl, (C
3
-C
8
)-cycloalkenyl or (C
3
-C
8
)-cycloalkyl-(C
1
-C
6
)-alkyl;
R
14
and R
15
independently of one another are hydrogen, (C
1
-C
6
)-alkyl, (C
1
-C
6
)-alkoxy, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkenyloxy, (C
2
-C
6
)-alkynyl, halogen-(C
1
-C
6
)-alkyl, (C
3
-C
8
)-cycloalkyl, cyano-(C
1
-C
6
)-alkyl, halogen-(C
2
-C
6
)-alkenyl, halogen-(C
2
-C
6
)-alkynyl, substituted or unsubstituted aryl or substituted or unsubstituted aryl-(C
1
-C
6
)-alkyl;
G is oxygen or 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 independently of one another are 0, 1 or 2;
o, p and q independently of one another are 0 or 1;
v is 1, 1, 2 or 3;
w is 0, 1, 2, 3 or 4.
A large number of compounds of the formula (I) according to the invention can exist in different tautomeric structures, depending on

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