1,2,3-thiadiazole derivatives, plant disease controller and...

Details 1,2,3-thiadiazole derivatives, plant disease controller and... 1,2,3-thiadiazole derivatives, plant disease controller and...

1999-11-10

2002-02-19

Ford, John M. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S224500, C514S230500, C514S224800, C544S092000, C544S093000, C544S089000, C544S050000, C544S032000

Reexamination Certificate

active

06348460

ABSTRACT:

TECHNICAL FIELD PERTINENT TO THE INVENTION
The present invention relates to 1,2,3-thiadiazole derivatives, plant disease controller containing said compounds as active ingredient thereof, and a method for using the same.
BACKGROUND ART
In JP-A-54-9272 are disclosed 1,2,3-thiadiazole-5-carboxylic acid derivatives, a method for producing said compounds, and compositions having herbicidal and plant growth regulating activities which contain said compounds. Further, in Canadian Patent No. 947297, JP-A-55-141476 and JP-A-56-108776, it is disclosed that benzoxazine derivatives are useful as herbicide.
The microorganisms and Eumycetes which are to be controlled with fungicides are characterized by rapidness of alteration of generations, and the problem of resistance to fungicides has long been discussed. Thus, it is desired to develop a novel fungicide having an excellent effect.
DISCLOSURE OF THE INVENTION
With the aim of developing a novel plant disease controller, the present inventors have continued elaborated studies to find that the 1,2,3-thiadiazole derivatives of the present invention represented by general formula (I) are useful as plant disease controller. Based on this finding, the present invention has been accomplished.
As typical compounds of the present invention, the 1,2,3-thiadiazole compounds represented by the following general formulas (I-a) and (I-b) can be referred to:
wherein R
1
, R
3
, R
4
, n, X and Y are as defined later,
wherein R
1
, R
5
, R
6
and m are as defined later.
That is, the present invention relates to 1,2,3-thiadiazole derivatives represented by the following general formula (I), a plant disease controller containing said compounds as active ingredient thereof, and a method for using the same:
[wherein R
1
represents hydrogen atom, halogen atom, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, hydroxy (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy (C
1
-C
6
) alkyl group, (C
3
-C
6
) cycloalkyl group, (C
1
-C
6
) alkoxycarbonyl (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkylcarbonyl (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkylcarbonyloxy (C
1
-C
6
) alkyl group, phenyl group, substituted phenyl group having 1 to 5, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group and halo (C
1
-C
6
) alkoxy group, phenyl (C
1
-C
6
) alkyl group, substituted phenyl (C
1
-C
6
) alkyl group having, on the ring thereof, 1 to 5, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group and halo (C
1
-C
6
) alkoxy group, phenoxy (C
1
-C
6
) alkyl group, substituted phenoxy (C
1
-C
6
) alkyl group having, on the ring thereof, 1 to 5, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group and halo (C
1
-C
6
) alkoxy group, phenylcarbonyloxy (C
1
-C
6
) alkyl group, substituted phenylcarbonyloxy (C
1
-C
6
) alkyl group having, on the ring thereof, 1 to 5, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, (C
1
-C
6
) alkyl group, halo (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy group and halo (C
1
-C
6
) alkoxy group or (C
1
-C
6
) alkoxycarbonyl group; and
R
2
represents the following formula (A):
 (wherein R
3
, which may be same or different, represents halogen atom, cyano group, nitro group, hydroxyl group, (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 or carboxyl group, n represents an integer of 0 to 3, and R
4
represents hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, (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 or carboxyl group, further, R
3
or R
3
and R
4
may be taken conjointly with a carbon atom of the adjacent phenyl group to form a (C
1
-C
6
) alkenylene ring, and X and Y may be same or different and represent oxygen atom or sulfur atom); or
the following formula (B):
 (wherein R
5
represents hydrogen atom, (C
1
-C
20
) alkyl group, halo (C
1
-C
20
) alkyl group, (C
2
-C
20
) alkenyl group, halo (C
2
-C
20
) alkenyl group, (C
2
-C
20
) alkynyl group, halo (C
2
-C
20
) alkynyl group, (C
3
-C
7
) cycloalkyl group, (C
3
-C
7
) cycloalkenyl group, (C
1
-C
6
) alkoxy (C
1
-C
6
) alkyl group, phenyl group, substituted phenyl group having 1 to 5, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, (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, hydroxyl group, carboxyl group, (C
1
-C
6
) alkoxycarbonyl group, carbamoyl group and aminocarbonyl group substituted with same or different hydrogen atoms or (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, 1 to 5, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, (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 and hydroxyl group, or a 5- or 6-membered heterocyclic group having at least one, same or different hetero atoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, further, said heterocyclic group may have, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, (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 and hydroxyl group;
R
6
represents (C
1
-C
20
) alkyl group, halo (C
1
-C
20
) alkyl group, (C
2
-C
20
) alkenyl group, halo (C
2
-C
20
) alkenyl group, (C
2
-C
20
) alkynyl group, halo (C
2
-C
20
) alkynyl group, (C
3
-C
7
) cycloalkyl group, (C
3
-C
7
) cycloalkenyl group, (C
1
-C
6
) alkoxy (C
1
-C
6
) alkyl group, phenyl group, substituted phenyl group having 1 to 5, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, (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 and hydroxyl group, phenyl (C
1
-C
6
) alkyl group, substituted phenyl (C
1
-C
6
) alkyl group having, on the ring thereof, 1 to 5, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, (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 and hydroxyl group, a 5- or 6-membered heterocyclic group having at least one, same or different hetero atoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, further, said heterocyclic group may have, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, (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 and hydroxyl group, or
—N(R
7
)R
8
 (wherein R
7
and R
8
, which may be same or different, represent (C
1
-C
20
) alkyl group, halo (C
1
-C
20
) alkyl group, cyano (C
1
-C
6
) alkyl group, (C
2
-C
20
) alkenyl group, halo (C
2
-C
20
) alkenyl group, (C
2
-C
20
) alkynyl group, halo (C
2
-C
20
) alkynyl group, (C
3
-C
7
) cycloalkyl group, (C
3
-C
7
) cycloalkenyl group, (C
1
-C
6
) alkoxy (C
1
-C
6
) alkyl group, (C
1
-C
6
) alkoxy (C
1
-C
6
) alkoxy (C
1
-C
6
) alkyl group, (C
1
-C
12
) alkylcarbonyl group, halo (C
1
-C
12
) alkylcarbonyl group, (C
1
-C
12
) alkoxycarbonyl group, (C
1
-C
12
) alkoxycarbonyl (C
1
-C
6
) alkyl group, (C
3
-C
7
) cycloalkylcarbonyl group, substituted (C
3
-C
7
) cycloalkylcarbonyl group substituted with at least one, same or different hal

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