Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-03-26
2001-02-27
Gerstl, Robert (Department: 1613)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S127000
Reexamination Certificate
active
06194444
ABSTRACT:
TECHNICAL FIELD
The present invention relates to 1,2,3-thiadiazole derivatives and salts thereof, and agrohorticultural disease controller containing said compound as an active ingredient, and method for using the disease controller.
BACKGROUND ART
1,2,3-Thiadiazoles are disclosed in JP-A-2-149579/1990 as an agent for treating central nervous system diseases, in JP-A-54-9272/1979, JP-A-3-181463/1991, JA-A-4-234881/1992, Canadian Patent 947297, etc. as a herbicide or a plant growth regulator, and in WO 9501340 and JP-A-7-252242/1995 as a fungicide.
DISCLOSURE OF THE INVENTION
With the aim of creating a novel agrohorticultural disease controller, the present inventors have conducted extensive studies to find that the 1,2,3-thiadiazole derivatives of the present invention represented by general formula (I) or salts thereof which are novel compounds not found in literature are useful as an agrohorticultural disease controller. Based on this finding, the present invention has been accomplished.
The present invention relates to 1,2,3-thiadiazole derivatives represented by the following general formula (I) or salts thereof, an agrohorticultural disease controller containing said compounds as an active ingredient, and a method for using said disease controller:
wherein R
1
represents hydrogen atom, C
1
-C
8
alkyl group, halo C
1
-C
4
alkyl group, phenyl group, substituted phenyl group having 1 to 5 same or different substituents selected from the group consisting of halogen atom, hydroxyl group, cyano group, nitro group, C
1
-C
4
alkyl group, halo C
1
-C
1
alkyl group, C
1
-C
4
alkoxy group, halo C
1
-C
4
alkoxy group and C
1
-C
4
alkoxycarbonyl group, 5- or 6-membered heterocycle containing 1 to 3 same or different heteroatoms selected from oxygen atom, nitrogen atom and sulfur atom, or substituted 5- or 6-membered heterocycle containing 1 to 3 same or different heteroatoms selected from oxygen atom, nitrogen atom and sulfur atom and having 1 to 4 same or different substituents selected from the group consisting of halogen atom, cyano group, hydroxyl group, mercapto group, C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group, C
1
-C
4
alkylthio group, formyl group, carboxyl group, carboxy C
1
-C
4
alkyl group, C
1
-C
4
alkoxycarbonyl group, C
1
-C
4
alkoxycarbonyl C
1
-C
4
alkyl group, amino group, substituted amino group having 1 or 2 same or different substituents selected from the group consisting of C
1
-C
4
alkyl and phenyl groups, carbamoyl group, substituted carbamoyl group having 1 or 2 same or different substituents selected from the group consisting of C
1
-C
4
alkyl and phenyl groups, carbamoyl C
1
-C
4
alkyl group, and substituted carbamoyl C
1
-C
4
alkyl group having 1 or 2 same or different substituents selected from the group consisting of C
1
-C
4
alkyl and phenyl groups;
A represents a group of the following formula:
(wherein R
2
and R
3
, same or different, represent hydrogen atom, halogen atom, cyano group, formyl group, C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group, C
1
-C
4
alkylthio group, C
1
-C
4
alkylsulfinyl group, C
1
-C
4
alkylsulfonyl group, C
1
-C
4
alkylcarbonyl group, C
1
-C
4
alkoxycarbonyl group, phenyl group, substituted phenyl group having 1 to 5 same or different substituents selected from the group consisting of halogen atom, hydroxyl group, cyano group, nitro group, C
1
-C
4
alkyl group, halo C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group, halo C
1
-C
4
alkoxy group and C
1
-C
4
alkoxycarbonyl group, phenylcarbonyl group, or substituted phenylcarbonyl group having, on the ring thereof, 1 to 5 same or different substituents selected from the group consisting of halogen atom, hydroxyl group, cyano group, C
1
-C
4
alkyl group and C
1
-C
4
alkoxycarbonyl group; further, R
2
and R
3
may be taken conjointly to form a 3- to 7-membered ring including a C
2
-C
6
alkylene group which may be intercepted by
—O—,
—S (O)
n
-in which n is an integer of 0 to 2,
—CO— or
—NR
8
— in which R
8
represents hydrogen atom, formyl group, C
1
-C
8
alkyl group, halo C
1
-C
4
alkyl group, C
2
-C
4
alkenyl group, halo C
2
-C
4
alkenyl group, C
2
-C
4
alkynyl group, halo C
2
-C
4
alkynyl group, C
1
-C
4
alkylthio group, C
1
-C
4
alkylsulfinyl group, C
1
-C
4
alkylsulfonyl group, C
1
-C
4
alkylcarbonyl group, C
1
-C
4
alkoxycarbonyl group, carbamoyl group, substituted carbamoyl group having 1 or 2 same or different substituents selected from the group consisting of C
1
-C
4
alkyl group and phenyl group, phenyl group, substituted phenyl group having 1 to 5 same or different substituents selected from the group consisting of halogen atom, cyano group, hydroxyl group, C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group and C
1
-C
4
alkoxycarbonyl group, phenyl C
1
-C
4
alkyl group, substituted phenyl C
1
-C
4
alkyl group having, on the ring thereof, 1 to 5 same or different substituents selected from the group consisting of halogen atom, cyano group, hydroxyl group, C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group and C
1
-C
4
alkoxycarbonyl group, phenylcarbonyl group, or substituted phenylcarbonyl group having, on the ring thereof, 1 to 5 same or different substituents selected from the group consisting of halogen atom, cyano group, hydroxyl group, C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group and C
1
-C
4
alkoxycarbonyl group; and said 3- to 7-membered ring may be substituted by one or more same or different substituents selected from the group consisting of halogen atom and C
1
-C
4
alkyl group; and m represents an integer of 0 to 4), or
in which R
2
and R
3
are as defined above, or
in which R
2
and R
3
are as defined above, or
in which R
2
and R
3
are as defined above; and
in the case that m is 0 in the definition of A, B represents cyano group, 5- or 6-membered heterocycle having 1 to 3 same or different hetero atoms selected from the group consisting of oxygen atom, nitrogen atom and sulfur atom, substituted 5- or 6-membered heterocycle containing 1 to 3 same or different hetero atoms selected from the group consisting of oxygen atom, nitrogen atom and sulfur atom and having 1 to 4 same or different substituents selected from the group consisting of halogen atom, cyano group, hydroxyl group, mercapto group, C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group, C
1
-C
4
alkylthio group, formyl group, carboxyl group, carboxy C
1
-C
4
alkyl group, C
1
-C
4
alkoxycarbonyl group, C
1
-C
4
alkoxycarbonyl C
1
-C
4
alkyl group, amino group, substituted amino group having 1 or 2 same or different C
1
-C
4
alkyl or phenyl groups, carbamoyl group, substituted carbamoyl group having 1 or 2 C
1
-C
4
alkyl or phenyl groups, carbamoyl C
1
-C
4
alkyl group and substituted carbamoyl C
1
-C
4
alkyl group having 1 or 2 same or different C
1
-C
4
alkyl or phenyl groups, or
—C(═X)R
4
(in which R
4
represents hydrogen atom, C
1
-C
8
alkyl group, halo C
1
-C
4
alkyl group, C
2
-C
4
alkenyl group, halo C
2
-C
4
alkenyl group, C
2
-C
4
alkynyl group, halo C
2
-C
4
alkynyl group, phenyl group, substituted phenyl group having 1 to 5 same or different substituents selected from the group consisting of halogen atom, cyano group, hydroxyl group, C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group and C
1
-C
4
alkoxycarbonyl group, phenyl C
1
-C
4
alkyl group, substituted phenyl C
1
-C
4
alkyl group having 1 to 5 same or different substituents selected from the group consisting of halogen atom, cyano group, hydroxyl group, C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group and C
1
-C
4
alkoxycarbonyl group, 5- or 6-membered heterocycle containing 1 to 3 same or different hetero atoms selected from the group consisting of oxygen atom, nitrogen atom and sulfur atom, or substituted 5- or 6-membered heterocycle containing 1 to 3 same or different hetero atoms selected from the group consisting of oxygen atom, nitrogen atom and sulfur atom and having 1 to 4 same or different substituents selected from the group consisting of halogen atom, cyano group, hydroxyl group, mercapto group, C
1
-C
4
alkyl group, C
1
-C
4
alkoxy group, C
1
-C
4
alkylthio group
Nishiguchi Tsutomu
Sampei Osamu
Shimaoka Takashi
Tajima Sohkichi
Takagi Kazuhiro
Gerstl Robert
Nihon Nohyaku Co., LTD
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