Triketone derivatives and herbicide

Details Triketone derivatives and herbicide Triketone derivatives and herbicide

2001-04-23

2004-06-29

Lambkin, Deborah C. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C549S058000

Reexamination Certificate

active

06756343

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a novel triketone derivative and a herbicide containing the triketone derivative as an active ingredient. More particularly, the invention relates to a triketone derivative useful for a herbicide effective on weeds which inhibit growth of crop plants, enter alia, for paddy field weeds such as
Echinochloa crus
-
galli
and
Scirups juncoides
, and to a herbicide containing the triketone derivative as an active ingredient.
BACKGROUND ART
Herbicides are important chemicals for facilitating weed control and enhancing productivity of field and garden crops. Therefore, development of herbicides which is safe and has excellent weed-controlling property even at a low dose have been actively carried out for many years.
There is proposed a herbicide containing a triketone derivative having a bicyclic benzoyl structure as an active ingredient, for the herbicide has excellent safety to field crops and excellent weed-controlling activity to field weeds. For example, there is proposed a herbicide containing a compound disclosed in Japanese Patent No. 2579663 and International Patent Publication WO97/08164 as an active ingredient, which herbicide has an excellent weed-controlling property suitable for growth of field crops. However, a herbicide containing such a compound as an active ingredient has poor activity for controlling paddy field weeds, and disadvantageously has insufficient safety to a paddy rice plant.
DISCLOSURE OF THE INVENTION
In view of the foregoing, an object of the present invention is to provide a herbicide containing a triketone derivative as an active ingredient, which herbicide can control a wide range of weeds at a low dose and imparts a low level of chemical injury to cultivated crops, particularly a paddy rice plant.
In order to attain the above object, the present inventors have conducted earnest studies, and have found that a triketone derivative having a specific chemical structure can control a wide range of weeds at a low dose and imparts a low level of chemical injury to cultivated crops. The present invention has accomplished based on this finding.
The present invention includes first and second aspects as described below.
The first aspect of the present invention encompasses the following.
(1) A triketone derivative represented by formula [I-1]:
 wherein R represents a methyl group; each of X and Y represents a hydrogen atom, a halogen atom, a nitro group, an amino group, a cyano group, a hydroxy group, a mercapto group, —R
1
, —OR
1
, —SR
1
, —SO
2
R
1
, —NR
2
R
3
, or —NHCOR
1
, wherein R
1
represents a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted; each of R
2
and R
3
represents a hydrogen atom, a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted, or R
2
and R
3
may be bonded to each other to form a group having a cyclic structure; M represents a hydrogen atom, an alkali metal, an alkaline earth metal, or an organic base; R
4
represents a hydrogen atom or a C1-C6 alkyl group; and m is an integer between 0 and 4 inclusive; provided that not all of X, Y, and R
4
simultaneously represent methyl groups.
(2) A triketone derivative represented by formula [I-2]:
 wherein R, X, Y, M, and m have the same definitions as described in relation to formula [I-1].
 (3) A triketone derivative represented by formula [I-3]:
 wherein R, X, M, R
4
, and m have the same definitions as described in relation to formula [I-1].
(4) A triketone derivative represented by formula [1-4):
 wherein R represents a methyl group; each of X and Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, —R
1
, —OR
1
, —SR
1
, or —NR
2
R
3
, wherein R
1
represents a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted; each of R
2
and R
3
represents a hydrogen atom, a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted, or R
2
and R
3
may be bonded to each other to form a group having a cyclic structure; Z represents —OR
1
, —SO
p
R
1
, —A(CH
2
)
n
QR
1
, —NR
2
R
3
, —N(OR
1
)R
2
, —O(C═O)R
1
, —O(C═O)OR
1
, —O(C═O)SR
1
, —O(C═O)NR
2
R
3
, or —O(C═S)NR
2
R
3
(wherein R
1
, R
2
, and R
3
have the same definitions as described in relation to X and Y, each of A and Q represents an oxygen atom or a sulfur atom, p is 0, 1, or 2, n is 1 or 2), —OM (wherein M represents a hydrogen atom, an alkali metal, an alkaline earth metal, or an organic base), or a halogen atom; and m is an integer between 0 and 4 inclusive.
(5) A triketone derivative according to (4), wherein Z represents an —OM group (wherein M represents a hydrogen atom, an alkali metal, an alkaline earth metal, or an organic base).
(6) A triketone derivative according to any one of (1), (2), (4), and (5), wherein Y represents a hydrogen atom, a C1-C6 alkyl group, or a halogen atom.
(7) A triketone derivative according to any one of (1), (2), (4), and (5), wherein Y represents a hydrogen atom or a methyl group.
(8) A triketone derivative according to any one of (2), (4), and (5), wherein Y represents a hydrogen atom.
(9) A triketone derivative according to any one of (1) to (8), wherein X represents —R
1
, —OR
1
, or —SR
1
.
(10) A triketone derivative according to (1) or (9), wherein X represents a halogen atom or a methyl group.
(11) A triketone derivative according to any one of (1) to
(10), wherein M represents a hydrogen atom.
(12) A herbicide containing a triketone derivative as recited in any one of (1) to (11) as an active ingredient.
(13) A herbicide for use in cultivation of a paddy rice plant, which herbicide contains a triketone derivative as recited in any one of (1) to (11) as an active, ingredient.
The second aspect of the present invention encompasses the following.
(1) A triketone derivative represented by formula [II-1]:
 wherein R represents a methyl group; X represents a hydrogen atom, a halogen atom, a nitro group, an amino group, a cyano group, a hydroxy group, a mercapto group, —R
1
, —OR
1
, —SR
1
, —SO
2
R
1
, —NR
2
R
3
, or —NHCOR
1
(wherein R
1
represents a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted; each of R
2
and R
3
represents a hydrogen atom, a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted, or R
2
and R
3
may be bonded to each other to form a group having a cyclic structure);
G contains 3 to 5 ring-constituting atoms which form a 5- to 7-membered saturated or unsaturated condensed ring including two carbon atoms of the benzene ring adjacent to G, wherein two or less ring-constituting atoms are selected from among nitrogen, oxygen, and sulfur, and the ring-constituting atoms may have

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