Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-05-06
2003-07-08
Morris, Patricia L. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S348000, C514S349000, C514S351000, C514S352000, C514S357000, C546S290000, C546S296000, C546S297000, C546S300000, C546S304000, C546S307000, C546S311000, C546S312000, C546S338000
Reexamination Certificate
active
06589967
ABSTRACT:
FIELD OF INVENTION
The present invention relates to novel oxime O-ether compounds and fungicides containing said compound as an active principle for agricultural and horticultural use.
BACKGROUND ART
For agricultural and horticultural crop culture, various agricultural plant protection chemicals have been used for controlling plant diseases. However, due to deterioration of plant protection chemicals in their activity and the appearance of resistant stains of plant pathogenic microorganisms to those chemicals, the use of fungicides plant protection use has been restricted. In addition, many fungicides cause phytotoxicity to plants or are toxic to humans and animals. Consequently, although there are many fungicides for plant protection use have been developed and used, most of them are not satisfactory in view of said disadvantages. As a result, there is a need yet to provide fungicides for plant protection use, which do not have the above-described disadvantages and can be used safely.
For example, oxime O-ether compounds similar to the compounds as defined in the present invention are disclosed in EP4754, EP24888, WO93/21157 as compounds having insecticidal and acaricidal activity.
Furthermore, it is disclosed in Jpn. Pat. Appln. Publication (KOKAI) No. 9-3047 that oxime O-ether compounds represent by the following chemical formula are useful as a fungicide.
DISCLOSURE OF THE INVENTION
It is an object of the present invention to provide novel oxime O-ether compounds, those which can be an excellent fungicide for agricultural and horticultural use, advantageous for the production in an industrial scale, having firm biological effectiveness, and causing less phytotoxicity.
The inventors of the present invention found that the fungicidal activity of said oxime O-ether compounds represented by the following general formula [I] can be enhanced and phytotoxicity caused thereby can be reduced by introducing an oxygen functional group into the 2nd position of the benzene ring of said oxime O-ether compound and a substituent into an arbitrary position, particularly the 6th position of the benzene ring.
Therefore, the present invention is directed to oxime O-ether compounds represented by a general formula [I];
wherein
R
1
represents C
1-6
alkyl, C
3-6
cycloalkyl, C
1-6
alkoxy, C
1-6
alkylthio, amino, mono- or di-(C
1-6
alkyl)amino, C
1-6
acyloxy, C
1-6
alkoxy C
1-6
alkyl, C
1-6
haloalkyl, hydroxy or Halogen atom;
m represents an integer of 1 to 4, and when m is 2 or more integer, each of R
1
may be same or different from one to another;
R
2
represents hydrogen atom, C
1-6
alkyl or C
3-6
cycloalkyl;
R
3
and R
4
are same or different from one to another and each independently represents hydrogen atom or C
1-6
alkyl;
R
5
represents hydrogen atom, C
1-6
alkyl, C
3-6
cycloalkyl, C
1-6
haloalkyl, C
1-6
alkoxy C
1-6
alkyl, C
1-6
alkoxy C
1-6
alkoxy C
1-6
alkyl, C
7-10
aralkyl, C
7-10
aralkyloxy C
1-6
alkyl, C
1-6
alkylcarbonyl, C
1-6
alkylsulfonyl or C
1-6
haloalkylsulfonyl;
R
6
represents C
1-6
alkyl, C
3-6
cycloalkyl, C
2-6
alkenyl, C
2-6
alkynyl, C
1-6
alkoxy, C
1-6
alkoxy C
1-6
alkoxy, C
1-6
alkylcarbonyloxy, C
1-6
alkoxy C
1-6
alkyl, C
1-6
haloalkyl, cyano, nitro, amino, mono- or di-(C
1-6
alkyl)amino, C
1-6
alkylcarbonylamino, C
1-6
alkylthio, hydroxy or Halogeno atom; and
n represents an integer of 1 to 4, and when n is 2 or more integer, each of R
6
may be same or different from one to another, and fungicides for agricultural and horticultural use containing the oxime O-ether compound or a salt thereof as the active ingredient.
More specifically, in the general formula [I],
R
1
represents 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,
an optionally-substituted C
3-6
cycloalkyl, such as cyclopropyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, and 1-methylcyclohexyl,
C
1-6
alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy, and t-butoxy,
C
1-6
alkylthio, such as methylthio, ethylthio, isopropylthio, and butylthio,
amino,
mono- or di-(C
1-6
alkyl)amino, ethylamino, propylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino, and ethylisopropylamino,
C
1-6
acyloxy, such as acetoxy, and propionyloxy, pivaloyloxy,
C
1-6
alkoxy C
1-6
alkyl, such as methoxymethyl, methoxyethyl, ethoxymethyl, propoxymethyl, and butoxymethyl;
C
1-6
haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl, and pentafluoroethyl;
hydroxy, or
Halogeno atom atom atom, such as fluorine, chlorine bromine and iodine;
m represents an integer of 1 to 4, and when m is 2 or more integer, each of R
1
may be same or different from one another;
R
2
represents hydrogen atom,
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, or
an optionally-substituted C
3-6
cycloalkyl, such as cyclopropyl, cyclopentyl, 1-methylcyclopentyl, cyclohexy, and 1-methylcyclohexyl;
R
3
and R
4
may be same or different from one to another and each independently represents hydrogen atom, or
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;
R
5
represents hydrogen atom,
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,
an optionally-substituted C
3-6
cycloalkyl, such as cyclopropyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, and 1-methylcyclohexyl,
C
1-6
haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl, and pentafluoroethyl,
C
1-6
alkoxy C
1-6
alkyl, such as methoxymethyl, methoxyethyl, ethoxymethyl, propoxymethyl, and butoxymethyl,
C
1-6
alkoxy C
1-6
alkoxy C
1-6
alkyl, such as methoxyethoxymethyl and ethoxyethoxymethyl,
C
7-10
aralkyl, such as benzyl and phenetyl,
C
7-10
aralkyloxy C1-6 alkyl, such as benzyloxymethyl and benzyloxyethyl,
C
1-6
alkylcarbonyl, such as acetyl, propionyl, and pivaloyl,
C
1-6
alkylsulfonyl, such as methanesulfonyl and ethanesulfonyl, or
C
1-6
haloalkylsulfonyl, such as chloromethylsulfonyl and trifluoromethylsulfonyl;
R
6
represents C
1-6
, such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, t-butyl, pentyl and its isomers, and hexyl and its isomers,
an optionally-substituted C
3-6
cycloalkyl, such as cyclopropyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, and 1-methylcyclohexyl,
C
2-6
alkenyl, such as vinyl, propenyl, and isopropenyl,
C
2-6
alkynyl, such as ethynyl, and propalgyl,
C
1-6
alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and t-butoxy,
C
1-6
alkoxy C
1-6
alkoxy, such as methoxymethoxy, methoxyethoxy, ethoxymethoxy, propoxymethoxy, and butoxymethoxy,
C
1-6
alkylcarbonyl, such as acetoxy, propionyloxy, and pivaloyloxy,
C
1-6
alkoxy C
1-6
alkyl, such as methoxymethyl, methoxyethyl, ethoxymethyl, propoxymethyl, and butoxymethyl,
C
1-6
haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl, and pentafluoroehtyl,
cyano, nitro, amino,
mono- or di-(C
1-6
alkyl)amino, such as methylamino, ethylamino, propylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino, and ethylisopropylamino,
C
1-6
alyklcarbonylamino, such as acetylamino, and, pivaloylamino,
C
1-6
alkylthio, such as methylthio, ethylthio, and isopropylthio,
hydroxy, or
Halogen atom, such as fluorine, chlorine, bromine and iodine; and
n represents an integer of 1 to 4, and when n is 2 or more integer, each of R
6
may be same or different from one another.
Of the
Ando Takahiro
Hamamura Hiroshi
Mitani Akira
Nakagawa Yuuki
Sano Hiroshi
LaPointe Dennis G.
Morris Patricia L.
Nippon Soda Co. Ltd.
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