Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-02-20
2002-12-10
Gerstl, Robert (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S280700, C548S204000, C548S205000
Reexamination Certificate
active
06492404
ABSTRACT:
FIELD OF INVENTION
The present invention relates to novel thiazolylcinnamonitriles and pest controlling agents containing the said compounds as active ingredients.
BACKGROUND ART
A large number of pest controlling agents, such as insecticides and acaricides, have been used so far. However, many of them are hardly satisfactory as controlling agents because of insufficient efficacy, restrictions on their use due to drug resistance problems, phytotoxicity or pollution on plants, or strong toxicity on humans, domestic animals and fish. Therefore, there has been a desire for the development of agents applicable safely and having less of the drawbacks mentioned above.
As for cinnamonitrile derivatives similar to the compounds of the present invention, for example, 3-hydroxy-2-(4-phenyl-2-thiazolyl)-cinnamonitriles are disclosed in Japanese Patent Laid-open No. Sho 53-92769, Japanese Patent Laid-open No. Sho 55-154963 and EP 189960, and their alkali metal and ammonium salts in Japanese Patent Laid-open No. Sho 55-154962. However, none of them has been put to practical use as insecticides because of insufficient efficacy and other problems.
Further, WO 95/29591 and Japanese Patent Laid-open No. Hei 10-158254 have disclosed cinnamonitrile derivatives, similar to the compounds of the present invention, that are useful as anti-fouling agents for aquatic adhesive organisms. There are, however, no descriptions on their insecticidal activities.
DISCLOSURE OF THE INVENTION
It is an object of the present invention to provide pest controlling agents containing thiazolylcinnamonitriles as active ingredients, that have sure efficacy and can be used safely.
The present invention is directed to compounds represented by Formula (1)
[wherein
A is halogen, C
1-6
alkyl, C
1-6
haloalkyl, C
1-6
alkoxy, optionally substituted C
3-6
cycloalkyl, optionally substituted pyridyl, optionally substituted thienyl, substituted phenyl or optionally substituted phenoxy;
B is hydrogen, halogen, C
1-6
alkoxycarbonyl, optionally substituted phenyl, C
1-6
alkyl, C
1-6
haloalkyl or C
3-6
cycloalkyl;
R is C
1-6
alkyl, a group of Formula COR
1
(wherein R
1
is C
1-12
alkyl, C
1-6
haloalkyl, optionally substituted C
3-6
cycloalkyl, C
1-6
alkoxy, C
1-6
alkoxy C
1-6
alkyl, C
1-6
alkylthio C
1-6
alkyl, mono-C
1-6
alkylamino, di-C
1-6
alkylamino, optionally substituted phenyl C
1-6
alkyl, optionally substituted phenoxy C
1-6
alkyl, optionally substituted phenylthio C
1-6
alkyl or optionally substituted phenyl), or a group of Formula SO
2
R
2
(wherein R
2
is C
1-6
alkyl or optionally substituted phenyl);
X is cyano, nitro, halogen, C
1-6
alkyl, C
1-6
haloalkyl, C
1-6
alkoxy, C
1-6
haloalkoxy, optionally substituted phenyl or optionally substituted phenoxy; and
n is an integer between 1 and 5], and pest controlling agents containing one or more of the said compounds as active ingredients.
In the above Formula (1),
A is halogen such as fluorine, chlorine, bromine and iodine;
C
1-6
alkyl such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, t-butyl, pentyl and its isomers, and hexyl and its isomers;
C
1-6
haloalkyl such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl and pentafluoroethyl;
C
1-6
alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and t-butoxy;
optionally substituted C
3-6
cycloalkyl such as cyclopropyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl and 1-methylcyclohexyl;
optionally substituted pyridyl, such as 2-pyridyl, 3-pyridyl and 4-pyridyl that may have substituents at arbitrary positions of the pyridine ring;
thienyl, such as 2-thienyl and 3-thienyl 1 that may have substituents at arbitrary positions of the thiophene ring;
phenyl having substituents at arbitrary positions of the benzene ring; or
phenoxy having optional substituents at arbitrary positions of the benzene ring.
Examples of substituents of the aforementioned pyridyl, thienyl, phenyl and phenoxy groups include halogens such as fluorine and chlorine; C
1-6
alkyl such as methyl and ethyl; C
1-6
alkoxy such as methoxy, ethoxy and isopropoxy; and nitro. These pyridyl, thienyl, phenyl and phenoxy groups may have two or more, same or different, substituents.
B is hydrogen;
halogen such as fluorine, chlorine, bromine and iodine;
C
1-6
alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl and t-butoxycarbonyl;
C
1-6
alkyl such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, t-butyl, pentyl and hexyl;
C
1-6
haloalkyl such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl and pentafluoroethyl; or
C
3-6
cycloalkyl such as cyclopropyl, cyclopentyl and cyclohexyl.
R is C
1-6
alkyl such as methyl, ethyl, propyl, isopropyl, butyl and t-butyl; or
a group represented by Formula COR
1
or SO
2
R
2
,
wherein R
1
is C
1-12
alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl and its isomers, hexyl and its isomers, heptyl and its isomers, nonyl and its isomers and dodecyl, and branched alkyl groups are particularly preferred;
C
1-6
haloalkyl such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl and pentafluoroethyl;
optionally substituted C
3-6
cycloalkyl such as cyclopropyl, 1-methylcyclopropyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl and 1-methylcyclohexyl;
C
1-6
alkoxy C
1-6
alkyl such as methoxymethyl, methoxyethyl, ethoxymethyl, propoxymethyl and butoxymethyl;
C
1-6
alkylthio C
1-6
alkyl such as methylthiomethyl, methylthioethyl, ethylthioethyl, ethylthiomethyl, propylthiomethyl and butylthiomethyl;
mono- or di-C
1-6
alkylamino such as methylamino, ethylamino, propylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino and ethylisopropylamino;
optionally substituted phenyl C
1-6
alkyl, such as benzyl, phenethyl and phenylpropyl that may have substituents at arbitrary positions of the benzene ring;
optionally substituted phenoxy C
1-6
alkyl, such as phenoxymethyl and phenoxyethyl that may have substituents at arbitrary positions of the benzene ring;
optionally substituted phenylthio C
1-6
alkyl, such as phenylthiomethyl, phenylthioethyl, phenylthiopropyl and phenylthiobutyl that may have substituents at arbitrary positions of the benzene ring; or
phenyl having optional substituents at arbitrary positions of the benzene ring.
R
2
is C
1-6
alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl and its isomers, and hexyl and its isomers, or phenyl having optional substituents at arbitrary positions of the benzene ring.
In these R
1
and R
2
, examples of benzene-ring substituents of the phenyl C
1-6
alkyl, phenylthio C
1-6
alkyl, phenoxy C
1-6
alkyl and phenyl groups include halogen such as fluorine and chlorine, C
1-6
alkyl such as methyl and ethyl, C
1-6
alkoxy such as methoxy, ethoxy and isopropoxy, and nitro. These benzene rings may have two or more, same or different, substituents.
X is cyano, nitro,
halogen such as chlorine, bromine and fluorine;
C
1-6
alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl and its isomers, and hexyl and its isomers;
C
1-6
haloalkyl such as chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, 1-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoroethyl;
C
1-6
alkoxy such as methoxy, ethoxy, propoxy, isopropoxy and butoxy;
C
1-6
haloalkoxy such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy and 1,1-difluoroethoxy;
optionally substituted phenyl, or
optionally substituted phenoxy.
Examples of substituents of these phenyl and phenoxy groups include halogen such as fluorine and chlori
Aoyagi Koichiro
Iwasa Takao
Shibata Yasushi
Takahashi Hidemitsu
Take Tomohiro
Gerstl Robert
LaPointe Dennis G.
Mason & Assoc., PA
Nippon Soda Co. Ltd.
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