Herbicidal oxadiazolidines

Details Herbicidal oxadiazolidines Herbicidal oxadiazolidines

2001-06-29

2004-05-18

Gerstl, Robert (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S132000

Reexamination Certificate

active

06737383

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to certain oxadiazolidines, processes for their preparation, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation. This invention also relates to mixtures of herbicides that have a synergistic effect on weeds or have a safening effect on crops while retaining or increasing weed control.
The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
Arch. Pharm
. (1974), 307, 7-12 discloses the chemical structures of N,N-substituted 4-aryloxazolidindiones. However, it does not disclose the compounds of the present invention.
SUMMARY OF THE INVENTION
This invention is directed to compounds and processes to prepare compounds of Formula 1 including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation:
wherein
Q is H; or C
1
-C
12
alkyl, C
3
-C
10
cycloalkyl, C
6
-C
14
bicycloalkyl, C
3
-C
12
alkenyl, C
3
-C
10
cycloalkenyl, C
6
-C
14
bicycloalkenyl or C
3
-C
12
alkynyl, each optionally substituted with one or more R
21
; or
Q is a 3- to 7-membered fully saturated or 5- to 7-membered partially saturated heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)
n
, then only one X may be present and (b) when two X are present in the ring, they cannot be bonded directly to each other; or
Q is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R
16
; and when Q is a 5- or 6-membered aromatic heterocyclic ring system containing a nitrogen, then Q is bonded through any available carbon or nitrogen atom by replacement of a hydrogen on said carbon or nitrogen atom; or
Q is phenyl optionally substituted with one or more substituents independently selected from the group consisting of R
16
, phenoxy and Z; or
Q is
Q is —C(R
14
)(═NOR
15
), —C(O)R
19
, —C(O)OR
19
, —C(O)SR
19
, —C(S)R
19
, —C(S)OR
19
, —C(S)SR
19
, —C(O)NR
23
R
24
, —C(S)NR
23
R
24
, —OR
19
, —NR
19
R
20
, —S(O)
n
R
19
or —S(O)
n
NR
19
R
20
;
each X is —O—, —S(O)
n
—, —N═, —NR
10
— or —Si(R
11
)
2
—;
Y is, together with the carbons to which it is attached, a fully or partially saturated 5-, 6- or 7-membered carbocyclic ring optionally substituted with one or more C
1
-C
4
alkyl groups; or
Y is, together, with the carbons to which it is attached, a fully or partially saturated 5-, 6- or 7-membered heterocyclic ring which contains one or two X and is optionally substituted with one or more R
12
, provided that when said heterocyclic ring contains two X, then one X is other than O;
Z is phenyl or a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each phenyl and heterocyclic ring system is optionally substituted with one or more R
16
;
R
1
is C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, C
1
-C
6
alkoxy, C
2
-C
6
alkoxyalkyl or C
2
-C
6
haloalkoxyalkyl; or R
1
is C
3
-C
7
cycloalkyl or C
3
-C
7
cycloalkenyl, each optionally substituted with one or more R
5
; or
R
1
is phenyl optionally substituted with one or more R
13
; or
R
1
is a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 3 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that the heterocyclic ring system contains no more than one oxygen and no more than one sulfur, and each heterocyclic ring system is optionally substituted with one or more R
16
;
R
2
is C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
7
cycloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, C
1
-C
6
alkoxy, C
2
-C
6
alkoxyalkyl, C
2
-C
6
haloalkoxyalkyl or NR
3
R
4
; or
R
2
is
R
1
and R
2
are taken together as —CH
2
CH
2
—, —CH
2
CH
2
CH
2
—, —CH
2
CH
2
CH
2
CH
2
—, —CH
2
CH
2
CH
2
CH
2
CH
2
— or —CH
2
CH
2
OCH
2
CH
2
—;
R
3
is C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl; or
R
3
is C
3
-C
7
cycloalkyl or C
3
-C
7
cycloalkenyl, each optionally substituted with one or more R
5
; or
R
3
is a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing 1 to 2 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, and each heterocyclic ring is optionally substituted with one or more R
5
; or
R
3
is phenyl optionally substituted with one or more R
26
groups; or
R
1
and R
3
are taken together with the two nitrogen atoms to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional third heteroatom selected from the group consisting of oxygen sulfur and nitrogen, and said heterocyclic ring is optionally substituted with one, or more R
9
; or
R
2
and R
13
, together with the two atoms to which they are attached and the atom between them, form a fully saturated 5-, 6- or 7-membered carbocyclic or heterocyclic ring containing one oxygen, one sulfur or one or two nitrogen atoms, said heterocyclic ring is optionally substituted with one or more R
12
, provided that when said heterocyclic ring contains two nitrogen atoms, they are other than bonded directly to each other;
R
4
is H or C
1
-C
4
alkyl; or
R
3
and R
4
are taken together with the nitrogen atom to which they are attached to form a saturated or partially saturated 5-, 6- or 7-membered heterocyclic ring containing an optional second heteroatom selected from the group consisting of oxygen, sulfur and nitrogen, and said heterocyclic ring is optionally substituted with 1-4 R
9
;
each R
5
is independently halogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy; or when two R
5
are attached to the same carbon, then said two R
5
groups are taken together as (═O);
each R
6
and R
7
are independently H or C
1
-C
4
alkyl;
R
8
is independently C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or C
1
-C
4
alkoxy,
each R
9
is independently C
1
-C
4
alkyl or C
1
-C
4
alkoxy; or when two R
9
are attached to the same carbon, then said two R
9
groups are taken together as (═O);
W is, together with the carbons to which it is attached, a fully or partially saturated 5-, 6- or 7-membered heterocyclic ring containing one or two X, provided that (a) when X is other than O or S(O)
n
, then only one X may be present; (b) when two X are present in the ring, they cannot be bonded directly to each other; and (c) said heterocyclic ring is bonded to the group (CR
17
R
18
)
q
through other than X;
R
10
is H, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
-C
4
alkenyl, C
3
-C
4
alkynyl, C
2
-C
4
alkoxycarbonyl or C
2
-C
4
alkylcarbonyl; or R
10
is phenyl optionally substituted with C
1
-C
3
alkyl, halogen, cyano, nitro or C
2
-C
4
alkoxycarbonyl;
each R
11
is C
1
-C
4
alkyl;
each R
12
is

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