Heterocyclic dicarboxylic acid diamide derivatives,...

Details Heterocyclic dicarboxylic acid diamide derivatives,... Heterocyclic dicarboxylic acid diamide derivatives,...

2002-04-10

2004-06-08

Berch, Mark L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S309000, C514S311000, C514S312000, C514S354000, C514S355000, C546S316000, C546S323000, C546S141000, C546S146000, C546S156000, C546S169000, C546S313000

Reexamination Certificate

active

06747041

ABSTRACT:

TECHNICAL FIELD
The present invention relates to heterocyclic dicarboxylic acid diamide derivatives, agricultural and horticultural insecticides containing any of said compounds as an active ingredient, and their usage.
BACKGROUND ART
JP-A-6-25190, JP-A-9-323974, WO9944992, JP-A-12-7661, JP-A-12-103708 and the like disclose compounds constituting a portion of the heterocyclic dicarboxylic acid diamide derivative of the present invention but do not describe or suggest the usefulness of the disclosed compounds as agricultural and horticultural insecticides at all.
The present inventors earnestly investigated in order to develop a novel agricultural and horticultural insecticide, and consequently found that heterocyclic dicarboxylic acid diamide derivatives represented by the general formula (I) of the present invention are novel compounds not known in any literature and that not only these compounds but also the compounds disclosed in the prior arts can be put to a novel use, whereby the present invention has been accomplished.
DISCLOSURE OF THE INVENTION
The present invention relates to heterocyclic dicarboxylic acid diamide derivatives represented by the general formula (I):
{wherein R
1
, R
2
and R
3
, which may be the same or different, are hydrogen atoms, (C
3
-C
6
)cycloalkyl groups, halo(C
3
-C
6
)cycloalkyl groups or —A
1
—(R
4
)r (wherein A
1
is a (C
1
-C
8
)alkylene group, a (C
3
-C
6
)alkenylene group or a (C
3
-C
6
)alkynylene group, R
4
, which may be the same or different, are hydrogen atoms; halogen atoms; cyano groups; nitro groups; halo(C
1
-C
6
)alkyl groups; (C
3
-C
6
)cycloalkyl groups; halo(C
3
-C
6
)cycloalkyl groups; (C
1
-C
6
)alkoxycarbonyl groups; di(C
1
-C
6
)alkoxyphosphoryl groups whose (C
1
-C
6
)alkoxy groups may be the same or different; di(C
1
-C
6
)alkoxythiophosphoryl groups whose (C
1
-C
6
)alkoxy groups may be the same or different; diphenylphosphino groups; diphenylphosphono groups; phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C
1
-C
6
)alkyl groups, halo(C
1
-C
6
)alkyl groups, (C
1
-C
6
)alkoxy groups, halo(C
1
-C
6
)alkoxy groups, (C
1
-C
6
)alkylthio groups, halo(C
1
-C
6
)alkylthio groups, (C
1
-C
6
)alkylsulfinyl groups, halo(C
1
-C
6
)alkylsulfinyl groups, (C
1
-C
6
)alkylsulfonyl groups and halo(C
1
-C
6
)alkylsulfonyl groups; heterocyclic groups; substituted heterocyclic groups having one or more substituents which may be the same or different and are selected from halogen atoms, (C
1
-C
6
)alkyl groups, halo(C
1
-C
6
)alkyl groups, (C
1
-C
6
)alkoxy groups, halo(C
1
-C
6
)alkoxy groups, (C
1
-C
6
)alkylthio groups, halo(C
1
-C
6
)alkylthio groups, (C
1
-C
6
)alkylsulfinyl groups, halo(C
1
-C
6
)alkylsulfinyl groups, (C
1
-C
6
)alkylsulfonyl groups and halo(C
1
-C
6
)alkylsulfonyl groups; or —A
2
—R
5
(wherein A
2
is —O—, —S—, —SO—, —SO
2
—, —N(R
6
)— (wherein R
6
is a hydrogen atom; a (C
1
-C
6
)alkylcarbonyl group; a halo(C
1
-C
6
)alkylcarbonyl group; a (C
1
-C
6
)alkoxycarbonyl group; a phenylcarbonyl group; a substituted phenylcarbonyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C
1
-C
6
)alkyl groups, halo(C
1
-C
6
)alkyl groups, (C
1
-C
6
)alkoxy groups, halo(C
1
-C
6
)alkoxy groups, (C
1
-C
6
)alkylthio groups, halo(C
1
-C
6
)alkylthio groups, (C
1
-C
6
)alkylsulfinyl groups, halo(C
1
-C
6
)alkylsulfinyl groups, (C
1
-C
6
)alkylsulfonyl groups and halo(C
1
-C
6
)alkylsulfonyl groups; a phenyl(C
1
-C
4
)alkoxycarbonyl group; a substituted phenyl(C
1
-C
4
)alkoxycarbonyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C
1
-C
6
)alkyl groups, halo(C
1
-C
6
)alkyl groups, (C
1
-C
6
)alkoxy groups, halo(C
1
-C
6
)alkoxy groups, (C
1
-C
6
)alkylthio groups, halo(C
1
-C
6
)alkylthio groups, (C
1
-C
6
)alkylsulfinyl groups, halo(C
1
-C
6
)alkylsulfinyl groups, (C
1
-C
6
)alkylsulfonyl groups and halo(C
1
-C
6
)alkylsulfonyl groups; a (C
1
-C
6
)alkylsulfonyl group; or a halo(C
1
-C
6
)alkylsulfonyl group), —C(═O)— or —C(═NOR
7
)— (wherein R
7
is a hydrogen atom; a (C
1
-C
6
)alkyl group; a halo(C
1
-C
6
)alkyl group; a (C
3
-C
6
)alkenyl group; a halo(C
3
-C
6
)alkenyl group; a (C
3
-C
6
)alkynyl group; a cyclo(C
3
-C
6
)alkyl group; a phenyl(C
1
-C
4
)alkyl group; or a substituted phenyl(C
1
-C
4
)alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C
1
-C
6
)alkyl groups, halo(C
1
-C
6
)alkyl groups, (C
1
-C
6
)alkoxy groups, halo(C
1
-C
6
)alkoxy groups, (C
1
-C
6
)alkylthio groups, halo(C
1
-C
6
)alkylthio groups, (C
1
-C
6
)alkylsulfinyl groups, halo(C
1
-C
6
)alkylsulfinyl groups, (C
1
-C
6
)alkylsulfonyl groups and halo(C
1
-C
6
)alkylsulfonyl groups), and R
5
is a hydrogen atom; a (C
1
-C
6
)alkyl group; a halo(C
1
-C
6
)alkyl group; a (C
3
-C
6
)alkenyl group; a halo(C
3
-C
6
)alkenyl group; a (C
3
-C
6
)alkynyl group; a halo(C
3
-C
6
)alkynyl group; a (C
3
-C
6
)cycloalkyl group; a halo(C
3
-C
6
)cycloalkyl group; a (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyl group; a (C
1
-C
6
)alkylthio(C
1
-C
6
)alkyl group; a formyl group; a (C
1
-C
6
)alkylcarbonyl group; a halo(C
1
-C
6
)alkylcarbonyl group; a (C
1
-C
6
)alkoxycarbonyl group; a mono(C
1
-C
6
)alkylaminocarbonyl group; a di(C
1
-C
6
)alkylaminocarbonyl group whose (C
1
-C
6
)alkyl groups may be the same or different; a mono(C
1
-C
6
)alkylaminothio-carbonyl group; a di(C
1
-C
6
)alkylaminothiocarbonyl group whose (C
1
-C
6
)alkyl groups may be the same or different; a di(C
1
-C
6
)alkoxyphosphoryl group whose (C
1
-C
6
)alkoxy groups may be the same or different; a di(C
1
-C
6
)alkoxythiophosphoryl group whose (C
1
-C
6
)alkoxy groups may be the same or different; a phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from halogen atoms, (C
1
-C
6
)alkyl groups, halo(C
1
-C
6
)alkyl groups, (C
1
-C
6
)alkoxy groups, halo(C
1
-C
6
)alkoxy groups, (C
1
-C
6
)alkylthio groups, halo(C
1
-C
6
)alkylthio groups, (C
1
-C
6
)alkylsulfinyl groups, halo(C
1
-C
6
)alkylsulfinyl groups, (C
1
-C
6
)alkylsulfonyl groups and halo(C
1
-C
6
)alkylsulfonyl groups; a phenyl(C
1
-C
4
)alkyl group; a substituted phenyl(C
1
-C
4
)alkyl group having on the ring one or more substituents which may be the same or different and are selected from halogen atoms, (C
1
-C
6
)alkyl groups, halo(C
1
-C
6
)alkyl groups, (C
1
-C
6
)alkoxy groups, halo(C
1
-C
6
)alkoxy groups, (C
1
-C
6
)alkylthio groups, halo(C
1
-C
6
)alkylthio groups, (C
1
-C
6
)alkylsulfinyl groups, halo(C
1
-C
6
)alkylsulfinyl groups, (C
1
-C
6
)alkylsulfonyl groups and halo(C
1
-C
6
)alkylsulfonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more substituents which may be the same or different and are selected from halogen atoms, (C
1
-C
6
)alkyl groups, halo(C
1
-C
6
)alkyl groups, (C
1
-C
6
)alkoxy groups, halo(C
1
-C
6
)alkoxy groups, (C
1
-C
6
)alkylthio groups, halo(C
1
-C
6
)alkylthio groups, (C
1
-C
6
)alkylsulfinyl groups, halo(C
1
-C
6
)alkylsulfinyl groups, (C
1
-C
6
)alkylsulfonyl groups and halo(C
1
-C
6
)alkylsulfonyl groups), and r is an integer of 1 to 4),
provided that R
1
and R
2
are not hydrogen atoms at the same time,
R
1
and R
2
may form a 4 to 7 membered ring by combining to each other, in which the ring may contain the same or different 1 to 3 hetero atoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom,
Het is a heterocyclic group represented by any of the following formulas Q1 to Q22:
 (wherein X, which may be the same or different, are halogen atoms; cyano groups; nitro groups; (C
3
-C
6
)cycloalkyl groups; halo(C
3
-C
6
)cycloalkyl groups; tri(C
1
-C
6
)alkylsilyl groups whose (C
1
-C
6
)alkyl groups may be the same or different; phenyl groups; substituted phenyl groups having one or more substituents which may be the same or diffe

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