N-(unsubstituted or...

Details N-(unsubstituted or... N-(unsubstituted or...

1998-08-12

2002-01-15

Rotman, Alan L. (Department: 1612)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C546S292000, C546S296000, C546S313000, C546S323000

Reexamination Certificate

active

06339045

ABSTRACT:

TECHNICAL FIELD
The present invention relates to N-(substituted or unsubstituted)-4-substituted-6-(substituted or unsubstituted) phenoxy-2-pyridine carboxamide or thiocarboxamide, a process for producing the above-mentioned compound and a herbicide containing the above-mentioned compound.
BACKGROUND ART
Certain kinds of N-(substituted or unsubstituted)-6-(substituted or unsubstituted) phenoxy-2-pyridine carboxamides or thiocarboxamides are disclosed in Japanese Patent Applications Laid-open (KOKAI) Nos. 4-290805(1992) and 4-217959(1992). Hitherto, various herbicides including such compounds have been proposed. However, there has been still a strong demand for providing herbicides having an excellent herbicidal effect, such as a herbicide capable of surely exhibiting a herbicidal effect even when used in a small amount, such that its amount existing in environment can be advantageously reduced; a herbicide capable of exhibiting a good selectivity between crop and weed irrespective of change in environmental conditions; a herbicide causing no phytotoxicity even after crop rotation or double-cropping; or the like.
The present invention has been achieved in view of the above-mentioned problems. It is an object of the present invention to provide a compound having an excellent herbicidal effect, i.e., those capable of surely exhibiting a herbicidal effect even when used in a small amount, showing a good selectivity between crop and weed, and causing no phytotoxicity even after crop rotation or double-cropping, a process for the production of such a compound, and a herbicide using such a compound.
As a result of the present inventors' earnest studies concerning chemical structures and physiological activities to plants for discovering novel industrially useful pyridine derivatives, it has been surprisingly found that by introducing a substituent group such as alkoxy group, alkylthio group, alkylamino group or dialkylamino group into the 4-position of pyridine ring, the obtained compound can exhibit an extremely high herbicidal effect as compared to those having a pyridine ring whose 4-position is unsubstituted, which have been described as suitable compounds in Japanese Patent Application Laid-open (KOKAI) No. 4-290805(1992). The present invention has been attained on the basis of the finding.
More specifically, it has been found that by introducing the above-mentioned substituent group into the 4-position of pyridine ring, there can be produced an N-(substituted or unsubstituted)-4-substituted-6-(substituted or unsubstituted) phenoxy-2-pyridine carboxamide or thiocarboxamide compound having a higher herbicidal activity than that of conventional ones.
DISCLOSURE OF THE INVENTION
That is, in a first aspect of the present invention, there is provided N-(substituted or unsubstituted)-4-substituted-6-(substituted or unsubstituted) phenoxy-2-pyridine carboxamide or thiocarboxamide represented by the general formula (I):
wherein R
1
is a C
1
to C
4
alkoxy 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
1
to C
4
alkyl)(C
7
to C
8
aralkyl)amino group;
A
1
may be substituted with X
1
, and is a C
1
to C
10
alkyl group, a C
2
to C
6
alkenyl group, a C
3
to C
6
alkynyl group, a C
3
to C
6
cycloalkyl group, a C
1
to C
10
alkoxy group, a C
3
to C
6
alkenyloxy group, a C
3
to C
6
alkynyloxy group, a C
1
to C
10
alkylamino group, a di(C
1
to C
6
alkyl)amino group, a phenyl group, a phenylamino group, an arylalkyl group (whose alkyl moiety has 1 to 3 carbon atoms), an arylalkyloxy group (whose alkyl moiety has 1 to 3 carbon atoms), an arylalkylamino group (whose alkyl moiety has 1 to 3 carbon atoms), an amino group or a hydroxyl group {wherein the chain-like hydrocarbon moiety of A
1
is constituted by a longest carbon chain as a main chain exclusive of a C
1
to C
4
alkyl group bonded as side chain to the main chain, and the C
1
to C
4
alkyl group as side chain is regarded as X
1
};
X
1
is a halogen atom, a C
1
to C
4
alkoxy group, a C
1
to C
4
alkylthio group, a C
1
to C
4
alkyl group {which is not bonded to a terminal position of A
1
when A
1
is a C
1
to C
10
alkyl group, a C
1
to C
10
alkoxy group, a C
1
to C
10
alkylamino group or a di(C
1
to C
6
alkyl)amino group}, a C
3
to C
6
cycloalkyl group, a C
1
to C
4
alkylcarbonyl group, a C
1
to C
4
alkylamino group, a di(C
1
to C
4
alkyl)amino group, a C
1
to C
4
alkylsulfonyl group, a C
1
to C
4
alkylsulfinyl group, a hydroxyl group, an amino group, a cyano group or a thiol group, wherein the alkyl moiety of X
1
may be substituted with halogen atom(s);
n is 0 or an integer selected from numbers of hydrogen atoms of A
1
which can be substituted with X
1
, and when n is an integer of not less than 2, X
1
s may be the same or different;
p and s are an integer of 0 to 2 with the proviso that the sum of p and s (p+s) is 2;
when p is 2, A
1
may be the same or different;
when p is 2 and two A
1
s are alkyl chains, the A
1
s may be directly bonded together to form a ring, or the A
1
s may be bonded to each other through an oxygen atom of the hydroxyl group or a nitrogen atom of the amino group or the C
1
to C
4
alkylamino group which groups are bonded to one of the A
1
s, to form a ring;
Y
1
is a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkyl 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 is not less than 2, Y
1
s may be the same or different; and
Z is an oxygen atom or a sulfur atom.
In a second aspect of the present invention, there is provided a process for producing N-substituted-4-substituted-6-(substituted or unsubstituted) phenoxy-2-pyridine carboxamide or thiocarboxamide represented by the general formula (I-a), which process comprises carrying out an addition reaction between 2-(metal-substituted)-4-substituted-6-(substituted or unsubstituted) phenoxy pyridine represented by the general formula (II) and substituted isocyanate (or isothiocyanate) represented by the general formula (III); and
substituting the metal with a proton.
wherein R
2
is a C
1
to C
4
alkoxy group, a C
1
to C
4
alkylthio group, a di(C
1
to C
4
alkyl)amino group or a (C
1
to C
4
alkyl)(C
7
to C
8
aralkyl)amino group;
A
2
may be substituted with X
2
, and is a C
1
to C
10
alkyl group, a C
3
to C
6
alkenyl group, a C
3
to C
6
alkynyl group, a C
3
to C
6
cycloalkyl group, a phenyl group or an arylalkyl group (whose alkyl moiety has 1 to 3 carbon atoms) {wherein the chain-like hydrocarbon moiety of A
2
is constituted by a longest carbon chain as a main chain exclusive of a C
1
to C
4
alkyl group bonded as side chain to the main chain, and the C
1
to C
4
alkyl group as side chain is regarded as X
2
};
X
2
is a halogen atom, a C
1
to C
4
alkoxy group, a C
1
to C
4
alkylthio group, a C
1
to C
4
alkyl group {which is not bonded to a terminal position of A
2
when A
2
is a C
1
to C
10
alkyl group}, a C
3
to C
6
cycloalkyl group or a di(C
1
to C
4
alkyl)amino group, wherein the alkyl moiety of X
2
may be further substituted with halogen atom(s);
n is 0 or an integer selected from numbers of hydrogen atoms of A
2
which can be substituted with X
2
, and when n is an integer of not less than 2, X
2
s may be the same or different;
Y
1
is a C
1
to C
4
haloalkyl group, a C
1
to C
4
alkyl 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 is an integer of not less than 2, Y
1
s may be the same or different;
Z is an oxygen atom or a sulfur 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 N-(substituted or unsubstituted)-4-substituted-6-(su

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