Pyrimidinylbenzimidazole and triazinylbenzimidazole...

Details Pyrimidinylbenzimidazole and triazinylbenzimidazole... Pyrimidinylbenzimidazole and triazinylbenzimidazole...

2001-05-08

2003-06-10

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C544S197000, C544S206000, C544S207000, C544S209000, C544S217000

Reexamination Certificate

active

06576631

ABSTRACT:

TECHNICAL FIELD
The present invention relates to novel pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultural/horticultural fungicides containing said derivatives as the active ingredients.
BACKGROUND ART
As compounds related to the pyrimidinylbenzimidazole derivatives of the present invention, 4-aminopyrimidine derivatives disclosed as pharmaceuticals in U.S. Pat. No. 5,525,604 and European Patent No. 640,599 and pyrimidine derivatives disclosed as herbicides in International Publication No. WO94/17059, are mentioned, but no disclosure regarding agricultural/horticultural fungicides has been made. French Patent No. 1,476,529 discloses benzimidazolyl sulfonamide derivatives having insecticidal and fungicidal activities, but no disclosure regarding the present compounds has been made. Further, as compounds related to the triazinylbenzimidazole derivatives of the present invention, triazine derivatives disclosed in JP-A-47-36837, JP-A-49-17677 and Kogyo Kagaku Zassi (Journal of Industrial Chemistry) vol 73, No. 5, p1000 (1970) as coloring agents for textile goods, may be mentioned, but no disclosure regarding agricultural/horticultural fungicides has been made. Further, anilinopyrimidine derivatives as production intermediates therefor have not been known.
The present invention provides novel pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultural/horticultural fungicides containing them as the active ingredients.
The present inventors have conducted extensive studies to create novel agricultural/horticultural fungicides and as a result, found that the pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives of the present invention (hereinafter referred to as compounds of the present invention) are novel compounds which are not disclosed in any literatures and have outstanding effects as agricultural/horticultural fungicides, and the present invention has been accomplished.
DISCLOSURE OF THE INVENTION
Namely, the present invention resides in a pyrimidinylbenzimidazole or triazinylbenzimidazole derivative represented by the general formula [I]:
wherein A is N or CR
3
, each of R
1
and R
2
which are independent of each other, is a hydrogen atom, a halogen atom, a (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group, a (C
2
-C
6
) alkynyl group, a (C
3
-C
6
) cycloalkyl group, a (C
1
-C
4
) haloalkyl group, a (C
1
-C
6
) alkoxy group, a (C
2
-C
6
) alkenyloxy group, a (C
2
-C
6
) alkynyloxy group, a (C
3
-C
6
) cycloalkoxy group, a (C
1
-C
4
) haloalkoxy group, a cyano (C
1
-C
4
) alkyloxy group, a (C
1
-C
4
) alkoxy (C
1
-C
4
) alkyloxy group, a (C
3
-C
6
) cycloalkyl (C
1
-C
4
) alkoxy group, a benzyloxy group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], a (C
1
-C
6
) alkylthio group, a (C
1
-C
4
) alkoxy (C
1
-C
4
) alkyl group, a phenoxy group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], a (C
1
-C
4
) alkylcarbonyl group, a formyl group, a phenyl group, a di(C
1
-C
4
) alkylamino group, a cyano group or a (C
1
-C
6
) alkylsulfonyl group, R
3
is a hydrogen atom, a (C
1
-C
6
) alkyl group, a (C
1
-C
6
) alkoxy group or a halogen atom, X is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group, a (C
2
-C
6
) alkynyl group, a (C
3
-C
6
) cycloalkyl group, a benzyl group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], a (C
1
-C
6
) alkoxy group, a (C
2
-C
6
) alkenyloxy group, a (C
2
-C
6
) alkynyloxy group, a (C
1
-C
6
) alkylthio group, a (C
1
-C
6
) alkylsulfonyl group, a phenoxy group, a (C
1
-C
4
) alkoxy (C
1
-C
4
) alkyl group, a (C
1
-C
4
) haloalkyl group, a (C
1
-C
4
) haloalkoxy group, a (C
1
-C
4
) alkylcarbonyl group, a (C
1
-C
4
) alkoxycarbonyl group, an amino group, a mono(C
1
-C
4
) alkylamino group, a di(C
1
-C
4
) alkylamino group, an anilino group or a phenyl group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], Y is a halogen atom, a nitro group, a cyano group, a (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group, a (C
2
-C
6
) alkynyl group, a (C
1
-C
6
) alkoxy group, a (C
2
-C
6
) alkenyloxy group, a (C
2
-C
6
) alkynyloxy group, a (C
1
-C
4
) haloalkoxy group, a (C
1
-C
6
) alkylthio group, a (C
1
-C
4
) alkoxy (C
1
-C
4
) alkyl group, a (C
1
-C
4
) haloalkyl group, a (C
1
-C
4
) alkylcarbonyl group, a (C
1
-C
4
) alkoxycarbonyl group, a benzoyl group, an amino group, a mono(C
1
-C
4
) alkylamino group, a di(C
1
-C
4
) alkylamino group, a phenyl group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group] or a phenoxy group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], and n is 0 or an integer of from 1 to 3}, an anilinopyrimidine or anilinotriazine derivative, as an intermediate therefor, represented by the general formula [XV]:
(wherein A is N or CR
3
, each of R
1
and R
2
which are independent of each other, is a hydrogen atom, a halogen atom, a (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group, a (C
2
-C
6
) alkynyl group, a (C
3
-C
6
) cycloalkyl group, a (C
1
-C
4
) haloalkyl group, a (C
1
-C
6
) alkoxy group, a (C
2
-C
6
) alkenyloxy group, a (C
2
-C
6
) alkynyloxy group, a (C
3
-C
6
) cycloalkoxy group, a (C
1
-C
4
) haloalkoxy group, a cyano (C
1
-C
4
) alkyloxy group, a (C
1
-C
4
) alkoxy (C
1
-C
4
) alkyloxy group, a (C
3
-C
6
) cycloalkyl (C
1
-C
4
) alkoxy group, a benzyloxy group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], a (C
1
-C
6
) alkylthio group, a (C
1
-C
4
) alkoxy (C
1
-C
4
) alkyl group, a phenoxy group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], a (C
1
-C
4
) alkylcarbonyl group, a formyl group, a phenyl group, a di(C
1
-C
4
) alkylamino group, a cyano group or a (C
1
-C
6
) alkylsulfonyl group, R
3
is a hydrogen atom, a (C
1
-C
6
) alkyl group, a (C
1
-C
6
) alkoxy group or a halogen atom, R
5
is an amino group, a nitro group or —NHCOX, X is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group, a (C
2
-C
6
) alkynyl group, a (C
3
-C
6
) cycloalkyl group, a benzyl group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], a (C
1
-C
6
) alkoxy group, a (C
2
-C
6
) alkenyloxy group, a (C
2
-C
6
) alkynyloxy group, a (C
2
-C
6
) alkylthio group, a (C
1
-C
6
) alkylsulfonyl group, a phenoxy group, a (C
1
-C
4
) alkoxy (C
1
-C
4
) alkyl group, a (C
1
-C
4
) haloalkyl group, a (C
1
-C
4
) haloalkoxy group, a (C
1
-C
4
) alkylcarbonyl group, a (C
1
-C
4
) alkoxycarbonyl group, an amino group, a mono(C
1
-C
4
) alkylamino group, a di(C
1
-C
4
) alkylamino group, an anilino group or a phenyl group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group], Y is a halogen atom, a nitro group, a cyano group, a (C
1
-C
6
) alkyl group, a (C
2
-C
6
) alkenyl group, a (C
2
-C
6
) alkynyl group, a (C
1
-C
6
) alkoxy group, a (C
2
-C
6
) alkenyloxy group, a (C
2
-C
6
) alkynyloxy group, a (C
1
-C
4
) haloalkoxy group, a (C
1
-C
6
) alkylthio group, a (C
1
-C
4
) alkoxy (C
1
-C
4
) alkyl group, a (C
1
-C
4
) haloalkyl group, a (C
1
-C
4
) alkylcarbonyl group, a (C
1
-C
4
) alkoxycarbonyl group, a benzoyl group, an amino group, a mono(C
1
-C
4
) alkylamino group, a di(C
1
-C
4
) alkylamino group, a phenyl group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy group] or a phenoxy group [said group may be substituted by a halogen atom, a (C
1
-C
4
) alkyl group or a (C
1
-C
4
) alkoxy g

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