Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-06-24
2004-03-23
McKane, Joseph K. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S365000, C546S269700, C548S146000
Reexamination Certificate
active
06710062
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a cyanomethylene compound, a process for preparing the same and an agricultural and horticultural fungicide which contains the compound.
BACKGROUND ART
Recent years have seen the emergence of drug resistant fungi due to long term use of fungicides. For this reason, it has become difficult to accomplish control by use of known fungicides such as benzimidazole. Consequently, there is a demand for development of new type of compounds having a fungicidal activity against drug resistant fungi.
As a compound having a cyanomethylene group bonded to the 2-position on the thiazolidine ring, a compound represented by the formula (A)
is disclosed, for example, in Phamazie, 53(6), 373-376 (1998) which reports that the compound has an antituberculous activity. However, the publication discloses nothing about the fungicidal activity of the compound of the formula (A).
WO96/33995 discloses oxopropionitrlle derivatives represented by the formula (B)
wherein Ra is an alkyl group having 2 to 8 carbon atoms, Rb is a hydrogen atom, etc., Rc is a heterocyclic group and Rd is a hydrogen atom, etc., and mentions that the derivatives have an insecticidal activity, but refers nowhere to a fungicidal activity of the derivatives.
DISCLOSURE OF THE INVENTION
An object of the invention is to provide a novel cyanomethylene compound which exhibits an excellent fungicidal activity against drug resistant fungi as well as drug sensitive fungi.
Another object of the invention is to provide a process for preparing the cyanomethylene compound.
A further object of the invention is to provide a new type of fungicide for agriculture and horticulture which exhibits a remarkable fungicidal effect against chemical-resistant fungi as well as chemical-sensitive fungi.
The invention provides cyanomethylene compounds represented by the formula (1) (hereinafter referred to as “cyanomethylene compound (1)”)
wherein R is C
1-20
straight-chain or branched-chain alkyl, C
3-8
cycloalkyl, aryl, aryl-C
1-4
alkyl or heterocyclic group; and the aryl, the aryl-C
1-4
alkyl and the heterocyclic group may be substituted with at least one substituent selected from the group consisting of halogen atom, C
1-4
alkyl, C
1-4
haloalkyl, C
1-4
alkoxy, C
1-4
haloalkoxy, C
1-4
alkoxycarbonyl, C
1-4
alkylaminocarbonyl, C
1-4
alkoxyimino-C
1-4
alkyl, C
1-4
alkylamino, C
1-4
alkylcarbonyl, C
1-4
alkylthio, aryl-C
1-4
alkyl, carbamoyl, phenoxy, benzyloxy, nitro and cyano;
R
1
is C
1-8
straight-chain or branched-chaln alkyl, C
3-8
cycloalkyl, aryl, aryl-C
1-4
alkyl or heterocyclic group; and the aryl, the aryl-C
1-4
alkyl and the heterocyclic group may be substituted with at least one substituent selected from the group consisting of halogen atom, C
1-4
alkyl, C
1-4
haloalkyl, C
1-4
alkoxy, C
1-4
haloalkoxy, C
1-4
alkoxycarbonyl, C
1-4
alkylamino, di-C
1-4
alkylamino, C
2-4
alkenyl, C
1-4
alkylthio, C
1-4
alkylsulfinyl, C
1-4
alkylsulfonyl, phenyl, phenoxy, nitro and cyano;
A is C
1-6
straight-chain or branched-chain alkylene, C
2-6
straight-chain or branched-chain alkenylene, —CH
2
—B—CH
2
— (wherein B is phenylene), —CH
2
—O—B—CH
2
— (wherein B is as defined above) or —Z—CO— (wherein Z is C
1-4
alkylene); and
Y is a sulfur atom, sulfinyl or sulfonyl.
The cyanomethylene compound (1) of the invention has a broad fungicidal spectrum, and an excellent fungicidal activity of controlling chemical-resistant fungi as well as chemical-sensitive fungi.
E/Z isomers are present in the cyanomethylene compound (1) of the invention. The cyanomethylene compound (1) of the invention includes an E/Z isomer and a mixture of E/Z isomers.
The invention provides a process for preparing the cyanomethylene compound (1), the process comprising reacting:
an isothiocyanate represented by the formula (2)
R
1
-NCS (2)
wherein R
1
is as defined above;
an acetonitrile represented by the formula (3)
R—Y—CH
2
—CN (3)
wherein R and Y are as defined above, and
a halogen compound represented by the formula (4)
X
1
—A—X
2
(4)
wherein A is as defined above, and X
1
and X
2
are the same or different and each represents halogen atom.
The invention provides a fungicide containing the cyanomethylene compound (1) for use in agriculture and horticulture.
In the formula (1), the groups represented by each of R, R
1
, A and Z can be exemplified as follows.
Examples of C
1-20
straight-chain or branched-chain alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-trldecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl and the like.
Examples of C
3-8
cycloalkyl are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like.
Examples of aryl are phenyl, naphthyl and the like.
Examples of aryl-C
1-4
alkyl are benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl and the like.
Examples of heterocyclic group are pyridyl, pyrimidyl, benzotriazolyl, 1,2,4-triazole-1-yl, 2-thienyl, pyrazinyl, pyridazinyl, 2-benzothiazolyl, oxazolyl, isoxazolyl, thiazolyl, 8-quinolyl, oxadiazolyl and the like.
Examples of halogen atom are fluorine, chlorine, bromine, iodine and the like.
Examples of C
1-4
alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and like C
1-4
straight-chain or branched-chain alkyl groups.
Examples of C
1-4
haloalkyl are fluoromethyl, bromomethyl, iodomethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 1-fluoroethyl, pentafluoroethyl, 1-fluoropropyl, 2-chloropropyl, 3-fluoropropyl, 3-chloropropyl, 1-fluorobutyl, 1-chlorobutyl, 4-fluorobutyl and like straight-chain or branched-chain alkyl substituted with 1 to 9 halogen atoms.
Examples of C
1-4
alkoxy are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy and like C
1-4
straight-chain or branched-chain alkoxy groups.
Examples of C
1-4
haloalkoxy are fluoromethoxy, chloromethoxy, bromomethoxy, iodomethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 1-fluoroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, 1-fluoropropoxy, 2-chloropropoxy, 3-fluoropropoxy, 3-chloropropoxy, 1-fluorobutoxy, 1-chlorobutoxy, 4-fluorobutoxy and like straight-chain or branched-chain alkoxy groups substituted with 1 to 9 halogen atoms.
Examples of C
1-4
alkoxycarbonyl are methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl and like alkoxycarbonyl groups wherein the alkoxy moiety is C
1-4
straight-chain or branched-chain alkoxy.
Examples of C
1-4
alkylaminocarbonyl are methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, isobutylaminocarbonyl, sec-butylaminocarbonyl, tert-butylaminocarbonyl and like alkylaminocarbonyl groups wherein the alkyl moiety is C
1-4
straight-chain or branched-chain alkyl.
Examples of C
1-4
alkoxyimino-C
1-4
alkyl are methoxyiminomethyl, ethoxyiminomethyl, 1-(n-propoxyimino)ethyl, isopropoxyiminomethyl, 2-(n,-butoxyimino)ethyl, sec-butoxyiminomethyl, tert-butoxyiminomethyl and like alkoxyiminoalkyl groups wherein the alkoxy moiety is C
1-4
straight-chain or branched-chain, and the alkyl moiety is C
1-4
straight-chain or branched-chain alkyl.
Examples of C
1-4
alkylamino are methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, tert-butylamino and like alkylamino groups wherein the alkyl moiety is C
1-4
straight-chain or branched-chain alkyl.
Examples of C
1-4
alkylcarobonyl are methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl and like alkylcarbonyl groups wherein the alkyl moiety is C
1-4
straight-chain or branched-chain alkyl.
Examples of C
1-8
straight-chain or branched-chain alkyl are methyl, ethyl, n-pro
Endo Yasuhiro
Hayashi Masatoshi
Komura Tomozo
Armstrong Kratz Quintos Hanson & Brooks, LLP
McKane Joseph K.
Otsuka Chemical Co. Ltd.
Saeed Kamal
LandOfFree
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