6-(Nonsubstituted or substituted) phenoxy picolinic acids,...

Details 6-(Nonsubstituted or substituted) phenoxy picolinic acids,... 6-(Nonsubstituted or substituted) phenoxy picolinic acids,...

1999-08-09

2001-03-13

Owens, Amelia (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S260000, C546S326000, C546S327000

Reexamination Certificate

active

06200933

ABSTRACT:

TECHNICAL FIELD
The present invention relates to 6-(unsubstituted or substituted) phenoxy picolinic acid, a process for producing the compound and an agricultural or horticultural fungicide containing the compound.
BACKGROUND ART
Certain kinds of 6-(unsubstituted or substituted) phenoxy picolinic acids have been described in Japanese Patent Applications Laid-open (KOKAI) Nos. 4-290805(1992), 4-217959(1992) or the like. However, in these prior arts, it has been only described that these compounds having a pyridine ring whose 3- to 5-positions are unsubstituted are usable as intermediates of herbicides. Therefore, there have been no descriptions concerning a fungicidal or germicidal activity of these compounds.
On the other hand, it has been demanded to provide compounds which are useful as agricultural or horticultural fungicides, and can show a low toxicity to human and cattle, a high safety upon handling and excellent control effects on extensive diseases of plants.
DISCLOSURE OF THE INVENTION
The present invention have been made in order to solve the above problems. It is an object of the present invention to provide an agricultural or horticultural fungicide which can exhibit a low toxicity to human and cattle, a high safety upon handling and an excellent control effect on extensive diseases of plants.
As a result of various studies by the present inventors for developing novel industrially useful pyridine derivatives, it has been found that 6-(unsubstituted or substituted) phenoxy picolinic acid has an excellent fungicidal or germicidal effect. The present invention has been attained on the basis of this finding.
That is, in a first aspect of the present invention, there is provided 6-(unsubstituted or substituted) phenoxy picolinic acid represented by the general formula (I-a):
wherein
R is a halogen atom, a C
1
to C
4
alkyl group, a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkoxy group, a C
1
to C
4
haloalkoxy group, a C
1
to C
4
alkylthio group, a C
1
to C
4
alkylamino group, a di(C
1
to C
4
alkyl)amino group or a C
7
to C
8
aralkyl(C
1
to C
4
alkyl)amino group;
n
1
is an integer of 1 to 3;
Y is a C
1
to C
4
alkyl group, a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkoxy group, a C
1
to C
4
haloalkoxy group, a C
1
to C
4
alkylthio group, a C
1
to C
4
haloalkylthio group or a halogen atom; and
m is an integer of 0 to 5, and when m and n
1
are not less than 2, Rs and Ys may be the same or different, respectively.
In a second aspect of the present invention, there is provided a process for producing 6-(unsubstituted or substituted) phenoxy picolinic acid represented by the general formula (I-b), which process comprises metallizing a 2-halogeno-6-(unsubstituted or substituted) phenoxy pyridine derivative represented by the general formula (III) to obtain 2-(metal-substituted)-6-(unsubstituted or substituted) phenoxy pyridine derivative represented by the general formula (II), reacting the obtained pyridine derivative (II) with carbon dioxide, and then subjecting the reaction product to proton-substitution.
wherein
R
1
is a halogen atom, a C
1
to C
4
alkyl group, a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkoxy group, a C
1
to C
4
haloalkoxy group, a C
1
to C
4
alkylthio group, a di(C
1
to C
4
) alkylamino group or a C
7
to C
8
aralkyl(C
1
to C
4
alkyl)amino group;
n
2
is an integer of 0 to 3;
Y is a C
1
to C
4
alkyl group, a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkoxy group, a C
1
to C
4
haloalkoxy group, a C
1
to C
4
alkylthio group, a C
1
to C
4
haloalkylthio group or a halogen atom;
m is an integer of 0 to 5, and when m and n
2
are not less than 2, R
1
s and Ys may be the same or different, respectively;
T
1
is a halogen atom; and
M is alkali metal, alkali earth metal-Q (wherein Q is a halogen atom), or ½(Cu-alkali metal).
In a third aspect of the present invention, there is provided a process for producing 6-(unsubstituted or substituted) phenoxy picolinic acid represented by the general formula (I-a), which process comprises hydrolyzing a 2-cyano-6-(unsubstituted or substituted) phenoxy pyridine derivative represented by the general formula (IV).
wherein
R is a halogen atom, a C
1
to C
4
alkyl group, a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkoxy group, a C
1
to C
4
haloalkoxy group, a C
1
to C
4
alkylthio group, a C
1
to C
4
alkylamino group, a di(C
1
to C
4
alkyl)amino group or a C
7
to C
8
aralkyl(C
1
to C
4
alkyl)amino group;
n
1
is an integer of 1 to 3;
Y is a C
1
to C
4
alkyl group, a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkoxy group, a C
1
to C
4
haloalkoxy group, a C
1
to C
4
alkylthio group, a C
1
to C
4
haloalkylthio group or a halogen atom; and
m is an integer of 0 to 5, and when m and n
1
are not less than 2, Rs and Ys may be the same or different, respectively.
In a fourth aspect of the present invention, there is provided a process for producing 6-(unsubstituted or substituted) phenoxy picolinic acid represented by the general formula (I-a), which process comprises hydrolyzing a 6-(unsubstituted or substituted) phenoxy picolinic acid ester represented by the general formula (V).
wherein
R is a halogen atom, a C
1
to C
4
alkyl group, a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkoxy group, a C
1
to C
4
haloalkoxy group, a C
1
to C
4
alkylthio group, a C
1
to C
4
alkylamino group, a di(C
1
to C
4
alkyl)amino group or a C
7
to C
8
aralkyl(C
1
to C
4
alkyl)amino group;
n
1
is an integer of 1 to 3;
Y is a C
1
to C
4
alkyl group, a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkoxy group, a C
1
to C
4
haloalkoxy group, a C
1
to C
4
alkylthio group, a C
1
to C
4
haloalkylthio group or a halogen atom;
m is an integer of 0 to 5, and when m and n
1
are not less than 2, Rs and Ys may be the same or different, respectively; and
B is a lower alkyl group.
In a fifth aspect of the present invention, there is provided an agricultural or horticultural fungicide containing 6-(unsubstituted or substituted) phenoxy picolinic acid represented by the general formula (I), as an effective ingredient.
wherein
R is a halogen atom, a C
1
to C
4
alkyl group, a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkoxy group, a C
1
to C
4
haloalkoxy group, a C
1
to C
4
alkylthio group, a C
1
to C
4
alkylamino group, a di(C
1
to C
4
alkyl) amino group or a C
7
to C
8
aralkyl(C
1
to C
4
alkyl)amino group;
n
2
is an integer of 0 to 3;
Y is a C
1
to C
4
alkyl group, a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkoxy group, a C
1
to C
4
haloalkoxy group, a C
1
to C
4
alkylthio group, a C
1
to C
4
haloalkylthio group or a halogen atom; and
m is an integer of 0 to 5, and when m and n
2
are not less than 2, Rs and Ys may be the same or different, respectively.
The present invention will be described in detail below.
First, the 6-(unsubstituted or substituted) phenoxy picolinic acid represented by the above general formula (I) (hereinafter referred to merely as “the present compound (I)”, is explained.
Examples of the halogen atoms as R of the present compound (I) may include a fluorine atom, a chlorine atom, a bromine atom or the like; as the C
1
to C
4
alkyl groups, there may be exemplified methyl, ethyl, propyl, isopropyl or the like; as the C
1
to C
4
haloalkyl groups, there may be exemplified trifluoromethyl, trichloromethyl or the like; as the C
1
to C
4
alkoxy groups, there may be exemplified methoxy, ethoxy, (1-methyl)ethoxy or the like; as the C
1
to C
4
haloalkoxy groups, there may be exemplified difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy or the like; as the C
1
to C
4
alkylthio groups, there may be exemplified methylthio, ethylthio or the like; as the C
1
to C
4
alkylamino groups, there may be exemplified methylamino, ethylamino or the like; as the di(C
1
to C
4
alkyl)amino groups, there may be exemplified dimethylamino, ethylmethylamino or the like; and as the C
7
to C
8
aralkyl(C
1
to C
4
alkyl)amino groups, there may be exemplified phenylmethyl(methyl)amino, phenylmethyl(ethyl)amino

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