Fused-heterocycle dicarboxylic acid diamide derivatives or...

Details Fused-heterocycle dicarboxylic acid diamide derivatives or... Fused-heterocycle dicarboxylic acid diamide derivatives or...

2001-01-26

2002-09-03

Dentz, Bernard (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C546S112000, C546S113000, C546S114000, C546S115000, C546S116000, C546S118000, C546S120000

Reexamination Certificate

active

06444617

ABSTRACT:

This application is the national phase of international application PCT/JP99/03009 filed Jul. 27, 1999 which designated the U.S.
TECHNICAL FIELD
The present invention relates to novel fused heterocyclic dicarboxylic acid diamide derivatives or salts thereof, a herbicide containing said compound or salt thereof as an active ingredient, and a method for using said herbicide.
BACKGROUND ART
In JP-A-6-25190, there is mentioned that pyrazinedicarboxylic acid diamide derivatives are useful as herbicide. In JP-A-9-323974, there is mentioned that pyridinedicarboxylic acid diamide derivatives are useful as herbicide.
DISCLOSURE OF THE INVENTION
The present inventors have conducted extensive studies with the aim of developing a novel herbicide. As a result, it has been found that the fused heterocyclic dicarboxylic acid diamide derivatives represented by general formula (I) of the present invention or salts thereof are novel compounds not found in literature and having an excellent herbicidal activity. Based on this finding, the present invention has been accomplished.
The present invention relates to fused heterocyclic dicarboxylic acid diamide derivatives represented by the following general formula (I):
wherein R
1
represents hydrogen atom or (C
1
-C
6
) alkyl group;
R
2
and R
3
may be same or different and each represents hydrogen atom, (C
1
-C
8
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
3
-C
8
) cycloalkyl group, (C
3
-C
6
) cycloalkyl (C
1
-C
6
) alkyl group, (C
3
-C
6
) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C
1
-C
6
) alkoxy group, (C
1
-C
6
) alkoxy (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkylthio group, alkylthio (C
1
-C
6
) alkyl group, cyano (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxycarbonyl (C
1
-C
6
) alkyl group, amino (C
1
-C
6
) alkyl group, substituted amino (C
1
-C
6
) alkyl group substituted with one or two, same or different (C
1
-C
6
) alkyl groups, phenyl (C
1
-C
6
) alkyl group, substituted phenyl (C
1
-C
6
) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C
1
-C
6
) alkyl groups, phenyl (C
1
-C
6
) alkoxy group or substituted phenyl (C
1
-C
6
) alkoxy group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C
1
-C
6
) alkyl groups; or
R
2
and R
3
, taken conjointly, represent a 5- to 6-membered heterocycle having at least one, same or different heteroatoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, further, the carbon atom or nitrogen atom on said heterocycle may have at least one, same or different substituents selected from the group consisting of halogen atom, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group, halo (C
1
-C
6
) alkoxy group, (C
1
-C
6
) alkylthio group and halo (C
1
-C
6
) alkylthio group;
X represents 0 to 5, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
3
-C
6
) cycloalkyl group, (C
3
-C
6
) cycloalkyl (C
1
-C
6
) alkyl group, (C
3
-C
6
) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C
1
-C
6
) alkoxy group, halo (C
1
-C
6
) alkoxy group, (C
1
-C
6
) alkylthio group, halo (C
1
-C
6
) alkylthio group, (C
1
-C
6
) alkyl-sulfinyl group, halo (C
1
-C
6
) alkylsulfinyl group, (C
1
-C
6
) alkylsulfonyl group, halo (C
1
-C
6
) alkylsulfonyl group, (C
1
-C
6
) alkoxy (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkylthio (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxycarbonyl group, amino group, substituted amino group substituted with same or different (C
1
-C
6
) alkyl groups, cyano (C
1
-C
6
) alkyl groups, phenyl (C
1
-C
6
) alkyl groups, (C
1
-C
6
) alkoxy-carbonyl (C
1
-C
6
) alkyl groups, (C
1
-C
6
) alkoxycarbonyl groups, (C
1
-C
6
) acyl groups, (C
1
-C
6
) alkylsulfonyl groups or halo (C
1
-C
6
) alkylsulfonyl groups, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group, halo (C
1
-C
6
) alkoxy group, (C
1
-C
6
) alkylthio group, halo (C
1
-C
6
) alkylthio group, (C
1
-C
6
) alkylsulfinyl group, halo (C
1
-C
6
) alkylsulfinyl group, (C
1
-C
6
) alkylsulfonyl group, halo (C
1
-C
6
) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group, halo (C
1
-C
6
) alkoxy group, (C
1
-C
6
) alkylthio group, halo (C
1
-C
6
) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group, halo (C
1
-C
6
) alkoxy group, (C
1
-C
6
) alkylthio group, halo (C
1
-C
6
) alkylthio group and phenyl group, phenyl (C
1
-C
6
) alkyl group or substituted phenyl (C
1
-C
6
) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group, halo (C
1
-C
6
) alkoxy group, (C
1
-C
6
) alkylthio group, halo (C
1
-C
6
) alkylthio group and phenyl group; and
 represents Q
1
, Q
2
, Q
3
, Q
4
, Q
5
, Q
6
, Q
7
, Q
8
, Q
9
, Q
10
, Q
11
, Q
12
, Q
13
, or Q
14
, wherein:
Q
1
is a group of the following formula:
wherein Y represents hydrogen atom, halogen atom, nitro group, cyano group, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
3
-C
6
) cycloalkyl group, (C
3
-C
6
) cycloalkyl (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group, halo (C
1
-C
6
) alkoxy group, (C
1
-C
6
) alkoxy (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkylthio group, halo (C
1
-C
6
) alkylthio group, (C
1
-C
6
) alkylsulfinyl group, halo (C
1
-C
6
) alkylsulfinyl group, (C
1
-C
6
) alkylsulfonyl group, halo (C
1
-C
6
) alkylsulfonyl group, (C
1
-C
6
) alkylthio (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group, halo (C
1
-C
6
) alkoxy group, (C
1
-C
6
) alkylthio group, halo (C
1
-C
6
) alkylthio group, (C
1
-C
6
) alkylsulfinyl group, halo (C
1
-C
6
,) alkylsulfinyl group, (C
1
-C
6
) alkylsulfonyl group, halo (C
1
-C
6
) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group, halo (C
1
-C
6
) alkoxy group, (C
1
-C
6
) alkylthio group, halo (C
1
-C
6
) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group, halo (C
1
-C
6
) alkoxy group, (C
1
-C
6
) alkylthio group, halo (C
1
-C
6
) alkylthio group and phenyl group, amino group, substituted amino group having at least one, same or different substituents selected from the group consisting of (C
1
-C
6
) alkyl group, cyano (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxycarbonyl (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxycarbonyl group, (C
1
-C
6
) alkoxyamino-carbonyl group, (C
1
-C
6
) acyl group, (C
1
-C
6
) alkylsulfonyl group, halo (C
1
-C
6
) alkylsulfonyl group and phenyl (C
1
-C
6
) alkyl group, (C
3
-C
6
) alkyleneimino group, hydrazino group or substituted hydrazino group substituted with same or different (C
1
-C
6
) alkyl

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