4-Quinolinol derivatives and agrohorticultural bactericides...

Details 4-Quinolinol derivatives and agrohorticultural bactericides... 4-Quinolinol derivatives and agrohorticultural bactericides...

2000-03-21

2004-01-20

Huang, Evelyn Mei (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S245000, C504S225000, C546S153000, C546S079000, C546S103000, C544S128000, C514S312000, C514S290000, C514S297000, C514S235200

Reexamination Certificate

active

06680282

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to 4-quinolinol derivatives and agricultural and horticultural fungicides containing them as active ingredients.
BACKGROUND OF THE INVENTION
JP-01246263A, JP-05202032A, JP-05271222A and JP-07285938A, which were published prior to the filing date of the present application, disclose that quinoline derivatives having a substituent, such as aryloxy, arylthio, amino, pyrimidyloxy, pyrimidylthio or benzoyl group, at 4-position of quinoline skeleton are effective against plant pathogenic fungi and useful as agricultural and horticultural fungicides. However, it has never known that a quinoline derivative having an acyloxy group at 4-position of quinoline skeleton has an excellent fungicidal activity.
And, JP-03128355A discloses 4-acyloxyquinoline derivatives structurally similar to the compound of the present invention and insecticidal and acaricidal agents containing them as active ingredients. However, it has never known that these compounds are effective against plant pathogenic fungi.
DISCLOSURE OF THE INVENTION
Many active agents having control effect against various plant diseases were discovered and various agricultural and horticultural fungicides containing them as active ingredients have been developed. Due to some problems, such as an appearance of resistant fungi, however, fungicides having higher control effect are needed.
Thus, an object of the present invention is to provide a new agricultural and horticultural fungicide having higher control effect.
The present inventors concentrated on solving the above-mentioned problem. As the result, it was found that among 4-quinolinol derivatives, 4-quinolinol derivatives having specific substituents at all of the 2, 3 and 5 to 8 positions of quinoline skeleton and their acid addition salts show excellent fungicidal activity against various plant pathogenic fungi causing blast of rice, brown spot of rice, powdery mildew of Cucurbitaceae, anthracnose of potato and the like, and thereby the present invention was completed.
Accordingly, the present invention relates to a 4-quinolinol derivative represented by the general formula (I):
wherein
R
1
represents
a hydrogen atom,
an alkali metal,
an alkaline earth metal, or
COR
4
in which R
4
is
a hydrogen atom,
an optionally substituted C
1
-C
18
alkyl group,
an optionally substituted C
2
-C
18
alkenyl group,
an optionally substituted C
3
-C
10
cycloalkyl group,
an optionally substituted phenyl lower alkyl group,
an optionally substituted phenoxy lower alkyl group,
an optionally substituted aryl group,
OR
5
in which R
5
is an optionally substituted lower alkyl group, an optionally substituted aryl group, an optionally substituted heterocycle, an optionally substituted phenyl lower alkyl group or an optionally substituted phenoxy lower alkyl group, or
NR
6
R
7
in which R
6
and R
7
are each a hydrogen atom, an optionally substituted C
1
-C
6
alkyl group or an optionally substituted phenyl group, or R
6
and R
7
together with N may form a four- to six-membered ring containing one or two heteroatoms;
R
2
represents an optionally substituted lower alkyl group;
R
3
represents
an optionally substituted C
1
-C
18
alkyl group,
an optionally substituted lower alkenyl group, or
an optionally substituted lower alkoxy group; or
R
2
and R
3
together represent —(CH
2
)m— in which m is 3 or 4; and
W represents 1 to 4 substituents on the nucleus which may be identical or different and each of which is
a halogen atom,
an optionally substituted C
1
-C
10
alkyl group,
an optionally substituted lower alkenyl group,
an optionally substituted lower alkynyl group,
an optionally substituted C
1
-C
10
alkoxy group,
an optionally substituted C
3
-C
10
cycloalkyl group,
an optionally substituted aryl group,
an optionally substituted aryloxy group,
NR
8
R
9
in which R
8
and R
9
are each a hydrogen atom, an optionally substituted C
1
-C
6
alkyl group or an optionally substituted phenyl group, or R
8
and R
9
together with N may form a four- to six-membered ring containing one or two heteroatoms,
COR
10
in which R
10
is a hydrogen atom, an optionally substituted lower alkyl group or an optionally substituted lower alkenyl group,
COOR
11
in which R
11
is a hydrogen atom, an optionally substituted lower alkyl group or an optionally substituted lower alkenyl group,
a nitro group or
a cyano group,
and acid addition salts thereof as well as an agricultural and horticultural fungicide containing at least one of them.
In the 4-quinolinol derivatives represented by the aforementioned general formula (I),
R
1
represents
a hydrogen atom,
an alkali metal, such as preferably sodium and potassium,
an alkaline earth metal, such as magnesium, calcium and barium, in which magnesium and calcium are preferable, or
COR
4
in which R
4
is
a hydrogen atom,
an optionally substituted C
1
-C
18
alkyl group, preferably an optionally substituted C
1
-C
8
alkyl group, more preferably a C
1
-C
4
alkyl group, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl and t-butyl,
an optionally substituted C
2
-C
18
alkenyl group, preferably an optionally substituted C
2
-C
8
alkenyl group, more preferably a C
2
-C
4
alkenyl group, such as vinyl group CH
2
═CH—, allyl group CH
2
═CHCH
2
— and 2-butenyl group CH
3
CH═CHCH
2
—,
an optionally substituted C
3
-C
10
cycloalkyl group, preferably an optionally substituted C
3
-C
6
cycloalkyl group,
an optionally substituted phenyl lower alkyl group,
an optionally substituted phenoxy lower alkyl group,
an optionally substituted aryl group,
OR
5
in which R
5
is an optionally substituted lower alkyl group, an optionally substituted aryl group, an optionally substituted heterocycle, an optionally substituted phenyl lower alkyl group or an optionally substituted phenoxy lower alkyl group, or
NR
6
R
7
in which R
6
and R
7
are each a hydrogen atom, an optionally substituted C
1
-C
6
alkyl group or an optionally substituted phenyl group, or R
6
and R
7
together with N may form a four- to six-membered ring containing one or two heteroatoms;
R
2
represents an optionally substituted C
1
-C
4
alkyl group;
R
3
represents
an optionally substituted C
1
-C
18
alkyl group, preferably an optionally substituted C
1
-C
6
alkyl group, more preferably a C
1
-C
4
alkyl group, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl and t-butyl,
an optionally substituted lower alkenyl group, or
an optionally substituted lower alkoxy group; or
R
2
and R
3
together represent —(CH
2
)m— in which m is 3 or 4; and
W represents 1 to 4 substituents on the nucleus which may be identical or different and each of which is
a halogen atom,
an optionally substituted C
1
-C
10
alkyl group,
an optionally substituted lower alkenyl group,
an optionally substituted lower alkynyl group,
an optionally substituted C
1
-C
10
alkoxy group,
an optionally substituted C
3
-C
10
cycloalkyl group,
an optionally substituted aryl group,
an optionally substituted aryloxy group,
NR
8
R
9
in which R
8
and R
9
are each a hydrogen atom, an optionally substituted C
1
-C
6
alkyl group or an optionally substituted phenyl group, or R
8
and R
9
together with N may form a four- to six-membered ring containing one or two heteroatoms,
COR
10
in which R
10
is a hydrogen atom, an optionally substituted lower alkyl group or an optionally substituted lower alkenyl group,
COOR
11
in which R
11
is a hydrogen atom, an optionally substituted lower alkyl group or an optionally substituted lower alkenyl group,
a nitro group, or
a cyano group.
Agriculturally and horticulturally acceptable acid addition salts of the 4-quinolinol derivative represented by the aforementioned general formula (I) mean salts generally usable in agriculture and horticulture, such as hydrochloride, nitrate, sulfate, phosphate and acetate.
The 4-quinolinol derivative represented by the aforementioned general formula (I) may be in the form of hydrate or solvate. Such hydrate and solvate of the compound represented by the general formula (I) are also included in the pres

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