Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-03-09
2001-08-28
Davis, Zinna Northington (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S255000, C546S339000, C546S340000, C546S344000, C514S277000
Reexamination Certificate
active
06281231
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel 2,6-dichloro-4-pyridinemethanol derivative and agricultural chemicals, particularly agents for controlling plant diseases, containing this compound as an active ingredient.
BACKGROUND ART
In agricultural production, there are needs for controlling various fungi pathogenic to plants, pests, weeds, and the like, and agricultural chemicals have hitherto been useful means therefor. However, there have been problems in that some compounds are phytotoxic for plants, and particularly for the crop plants to which the agricultural chemicals are applied, even though these compounds have excellent activity as agricultural chemicals, or in that even compounds which are not phytotoxic are not effective enough for practical use. Accordingly, production of compounds which are greatly effective as agricultural chemicals and which have little phytotoxicity has always been demanded.
Japanese Patent No. 2514823 and Japanese Patent Application, First Publication (Kokai), No. 1-283270, disclose that 2,6-dichloroisonicotinic acid derivatives having specific structures are active in protecting crop plants from pathogenic microorganisms. However, these compounds are phytotoxic for some types of crops, although these compounds were effective.
On the other hand, 2,6-dichloro-4-pyridinemethanol, to which the present invention relates, can be synthesized, for example, by bringing about a reduction reaction using 2,6-dichloroisonicotinic acid or an ester thereof as a starting material. (J. Prakt. Chem., Vol. 134, pp. 177-187 (1932); West German Patent Publication No. 3,615,293) However, neither a 2,6-dichloro-4-pyridinemethanol derivative according to the present invention nor use of 2,6-dichloro-4-pyridinemethanol and a 2,6-dichloro-4-pyridinemethanol derivative as an agricultural chemical has been known.
The object to be achieved by the present invention is to provide a novel compound with which there is little possibility of phytotoxicity for crop plants, and which is greatly effective in controlling various plant diseases caused by viruses pathogenic to plants, by bacteria, and by molds, and to provide agricultural chemicals, particularly agents for controlling plant diseases, containing this compound, i.e., 2,6-dichloro-4-pyridinemethanol, and/or a benzoic acid ester thereof as an active ingredient.
DISCLOSURE OF INVENTION
As a result of investigations in order to achieve the above object, the present inventors have arrived at the present invention, finding that a 2,6-dichloro-4-pyridinemethanol derivative which is expressed by general formula (1) is effective as an agricultural chemical, and particularly for controlling plant diseases, with a small amount used, and that there is no possibility of the compound being phytotoxic for plants.
That is to say, the present invention includes:
(a) a 2,6-dichloro-4-pyridinemethanol derivative expressed by the following general formula (1):
wherein W denotes: a C
1
to C
8
alkyl group which is unsubstituted or which is optionally substituted with an alkoxy group, an alkylthio group, a cyano group, a phenyl group, or a pyridyl group, the pyridyl group being optionally substituted with a halogen atom; a trifluoromethylpyridyl group; —COR
1
; —SO
2
R
2
; —PO(OR
3
)
2
; —CONHR
4
; —COOR
4
; —COCOR
4
; or —SiR
5
R
6
R
7
;
R
1
denotes:
a C
1
to C
18
alkyl group which is unsubstituted or which is optionally substituted with an alkoxy group, an alkylthio group, a phenyl group, a hydroxy group, a phenylalkoxy group, a phenylalkylthio group, an alkyloxycarbonyl group, an alkylcarbonylamino group, or a phenoxy group, the phenyl group being optionally substituted with an alkoxy group;
a C
1
to C
18
alkenyl group which is optionally substituted with a phenyl group, the phenyl group being optionally substituted with an alkoxy group;
a phenyl group which has one or more substituent groups, being the same or different, the substituent groups being selected from: halogen atoms; C
1
to C
6
alkyl groups which are optionally substituted with a halogen atom; C
1
to C
12
alkoxy groups which are optionally substituted with a halogen atom; C
2
to C
3
alkenyloxy groups; a nitro group; an amino group; C
1
to C
4
alkylamino groups; a cyano group; an acetylamino group; a benzoylamino group; an acetyloxy group; a phenyl group; and a phenoxy group; or
a 5- or 6-membered heterocyclic ring residue which has any one of a nitrogen atom, an oxygen atom, or a sulfur atom as a ring component atom, the heterocyclic ring residue being optionally substituted with a C
1
to C
4
alkyl group;
R
2
denotes a C
1
to C
12
alkyl group or a phenyl group which is optionally substituted with a C
1
to C
12
alkyl group;
R
3
denotes a C
1
to C
4
alkyl group;
R
4
denotes a C
1
to C
3
alkyl group or a phenyl group; and each of R
5
to R
7
, being the same or different, denotes a C
1
to C
4
alkyl group;
(b) a 2,6-dichloro-4-pyridinemethanol derivative as described in (a), wherein W in general formula (1) denotes a C
1
to C
8
alkyl group or a trifluoromethylpyridyl group, the Cto C
8
alkyl group being unsubstituted or being optionally substituted with an alkoxy group, an alkylthio group, a cyano group, a phenyl group, or a pyridyl group, the pyridyl group being optionally substituted with a halogen atom;
(c) a 2,6-dichloro-4-pyridinemethanol derivative as described in (a), wherein W in general formula (1) denotes —COR
1
in which R
1
denotes:
a C
1
to C
18
alkyl group which is unsubstituted or which is substituted with an alkoxy group, an alkylthio group, a phenyl group, a hydroxy group, a phenylalkoxy group, a phenylalkylthio group, an alkyloxycarbonyl group, an alkylcarbonylamino group, or a phenoxy group, the phenyl group being optionally substituted with an alkoxy group;
a C
1
to C
18
alkenyl group which is unsubstituted or which is substituted with a phenyl group which is optionally substituted with an alkoxy group;
a phenyl group which has one or more substituent groups, being the same or different, the substituent groups being selected from: halogen atoms; C
1
to C
6
alkyl groups which are optionally substituted with a halogen atom, C
1
to C
12
alkoxy groups which are optionally substituted with a halogen atom; C
2
to C
3
alkenyloxy groups; a nitro group; an amino group; C
1
to C
4
alkylamino groups; a cyano group; an acetylamino group; a benzoylamino group; an acetyloxy group; a phenyl group; and a phenoxy group; or
a 5- or 6-membered heterocyclic ring residue which has any one of a nitrogen atom, an oxygen atom, or a sulfur atom as a ring component atom, the heterocyclic ring residue being optionally substituted with a C
1
to C
4
alkyl group;
(d) a 2,6-dichloro-4-pyridinemethanol derivative as described in (c), wherein W in general formula (1) denotes —COR
1
in which R
1
denotes an alkenyl group which is unsubstituted or which is substituted with a phenyl group which is optionally substituted with an alkoxy group;
(e) a 2,6-dichloro-4-pyridinemethanol derivative as described in (c), wherein W in general formula (1) denotes —COR
1
in which R
1
denotes a phenyl group which has one or more substituent groups, being the same or different, the substituent groups being selected from: halogen atoms; C
1
to C
6
alkyl groups which are optionally substituted with a halogen atom; C
1
to C
12
alkoxy groups which are optionally substituted with a halogen atom; C
2
to C
3
alkenyloxy groups; a nitro group; an amino group; C
1
to C
4
alkylamino groups; a cyano group; an acetylamino group; a benzoylamino group; an acetyloxy group; a phenyl group; and a phenoxy group;
(f) a 2,6-dichloro-4-pyridinemethanol derivative as described in (e), wherein W in general formula (1) denotes —COR
1
in which R
1
denotes a C
1
to C
12
alkoxyphenyl group which is optionally substituted with a halogen atom;
(g) a 2,6-dichloro-4-pyridinemethanol derivative as described in (a), wherein W in general formula (1) denotes —SO
2
R
2
in which R
2
denotes a C
1
to C
12
alkyl group or a phenyl group which is optionally substituted w
Asada Toru
Gotou Takashi
Iiyama Mika
Tsuboi Hiroyuki
Armstrong Westerman Hattori McLeland & Naughton LLP
Dainippon Ink and Chemical Inc.
Davis Zinna Northington
LandOfFree
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