Triazolone derivatives, use thereof, and intermediates therefor

Details Triazolone derivatives, use thereof, and intermediates therefor Triazolone derivatives, use thereof, and intermediates therefor

2001-02-05

2002-12-03

Raymond, Richard L. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S263800, C548S264600, C546S272400, C544S333000, C504S239000, C504S253000, C504S273000, C514S256000, C514S339000, C514S384000

Reexamination Certificate

active

06489487

ABSTRACT:

ART FIELD RELATED
The present invention relates to triazolone derivatives, use thereof, and intermediates therefor.
OBJECTS OF THE INVENTION
An object of the present invention is to provide compounds having excellent plant disease control activity.
SUMMARY OF THE INVENTION
As a result of the present inventors' intensive study, it has been found that triazolone derivatives represented by the following formula [I] have excellent plant disease control activity. Thus, the present invention has been completed.
That is, the present invention provides a triazolone derivative represented by the formula [I]
wherein
R
1
represents optionally substituted C
1-10
alkyl, optionally substituted C
2-10
alkenyl, optionally substituted C
2-10
alkynyl, halogen (chlorine, bromine, iodine or fluorine), nitro, cyano, optionally substituted C
3-10
cycloalkyl, optionally substituted C
4-20
cycloalkylalkyl, optionally substituted C
5-10
cycloalkenyl, optionally substituted C
6-20
cycloalkenylalkyl, optionally substituted C
6-10
aryl, optionally substituted C
7-20
arylalkyl, optionally substituted C
1-9
heteroaryl, optionally substituted C
2-19
heteroarylalkyl, A
1
—L
1
—, A
1
—ON═CA
2
—, A
1
—ON═C(Me)CH
2
ON═CA
2
—, A
1
C(A
2
)═NOCH
2
—, A
1
SC(A
2
)═N—, A
1
C(═S)NH—, A
1
SC(═S)NH—, A
1
SC(SA
2
)═N—, A
1
—ON═C(CN)—, A
1
—ON═C(Me)CH
2
ON═C(CN)—, or A
1
C(CN)═NOCH
2
— (wherein L
1
represents oxygen, sulfur, carbonyl, —OCH
2
—, —SCH
2
—, —C(═O)O—, —OC(═O)—, —C(═O)OCH
2
—, —NH—, or C
1-6
alkylimino; A
1
and A
2
are the same or different, and each represents optionally substituted C
1-10
alkyl, optionally substituted C
2-10
alkenyl, optionally substituted C
2-10
alkynyl, optionally substituted C
3-10
cycloalkyl, optionally substituted C
4-20
cycloalkylalkyl, optionally substituted C
5-10
cycloalkenyl, optionally substituted C
6-20
cycloalkenylalkyl, optionally substituted C
6-10
aryl, optionally substituted C
7-20
arylalkyl, hydrogen, optionally substituted C
1-9
heteroaryl, or optionally substituted C
2-19
heteroarylalkyl);
R
2
represents hydrogen, or C
1-6
alkyl;
R
3
represents C
1-6
alkoxy, C
1-6
alkylthio, cyano, halogen, vinyl, ethynyl, cyclopropyl, or C
1-6
alkyl;
one of T, U and V represents CR
4
, another one represents CH or nitrogen, and the remaining one represents CR
5
or nitrogen; and
W represents CR
6
or nitrogen;
(wherein R
4
, R
5
and R
6
are the same or different, and each represents hydrogen, halogen, C
1-6
alkyl, C
1-6
alkoxy, C
1-6
haloalkyl, C
1-6
haloalkoxy, cyano, nitro, C
2-6
alkoxycarbonyl, C
1-6
alkylthio, or C
1-6
haloalkylthio) (hereinafter referred to as the compound of the present invention). Further, the present invention provides an agricultural or horticultural fungicide composition comprising as an active ingredient the compound of the present invention.
The present invention also provides intermediates useful for producing (a part of) the compound of the present invention, that is, an alkoxytriazolone compound represented by the formula [II-1]
wherein
R
31
represents C
1-6
alkyl (e.g., methyl, ethyl, etc.);
a boron compound represented by the formula [III-1]
 wherein both R
14
bind to each other at the terminal ends thereof to represent ethylene or trimethylene (they may be substituted with one or more methyl or phenyl, respectively) (e.g., —C(CH
3
)
2
—C(CH
3
)
2
—, —CH
2
CH
2
—, —CH
2
CH
2
CH
2
—, —CH
2
—C(CH
3
)
2
—CH
2
—, —CH(Ph)—CH
2
—CH(Ph)—, etc.), or it represents C
1-6
alkyl (e.g., methyl, ethyl, isopropyl, etc.) or hydrogen; and R
2
, R
3
, V, U, T and W are as defined above; and
a triazolone compound represented by the formula [IV]
 wherein R
1
, R
2
, R
3
, V, U, T and W are as defined above.
DETAILED DESCRIPTION OF THE INVENTION
In the present invention, as the C
1-10
alkyl of the optionally substituted C
1-10
alkyl represented by R
1
, A
1
and A
2
, for example, there are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, 1-methylpropyl, pentyl, 1-methylbutyl, 1-ethylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, hexyl, 1-methylpentyl, 1-ethylpentyl, 3,3-dimethylbutyl, heptyl, 3,7-dimethyloctyl, and the like.
As the C
2-10
alkenyl of the optionally substituted C
2-10
alkenyl represented by R
1
, A
1
and A
2
, for example, there are vinyl, allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 2-pentenyl, 3-methyl-2-butenyl, and the like.
As the C
2-10
alkynyl of the optionally substituted C
2-10
alkynyl represented by R
1
, A
1
and A
2
, for example, there are ethynyl, propargyl, 1-methyl-2-propynyl, 2-butynyl, and the like.
As the halogen represented by R
1
, there is chlorine, bromine, iodine or fluorine.
As the C
3-10
cycloalkyl of the optionally substituted C
3-10
cycloalkyl represented by R
1
, A
1
and A
2
, for example, there are cyclopropyl, cyclopentyl, cyclohexyl, and the like.
As the C
4-20
cycloalkylalkyl of the optionally substituted C
4-20
cycloalkylalkyl represented by R
1
, A
1
and A
2
, for example, there are cyclopropylmethyl, cyclopentylmethyl, 2-cyclopentylethyl, cyclohexylmethyl, and the like.
As the C
5-10
cycloalkenyl of the optionally substituted C
5-10
cycloalkenyl represented by R
1
, A
1
and A
2
, for example, there are cyclopentenyl, cyclohexenyl, and the like.
As the C
6-20
cycloalkenylalkyl of the optionally substituted C
6-20
cycloalkenylalkyl represented by R
1
, A
1
and A
2
, for example, there are cyclopentene-1-ylmethyl, cyclohexene-1-ylmethyl, and the like.
As the C
6-10
aryl of the optionally substituted C
6-10
aryl represented by R
1
, A
1
and A
2
, for example, there are phenyl, &agr;-naphthyl, &bgr;-naphthyl, and the like.
As the C
7-20
arylalkyl of the optionally substituted C
7-20
arylalkyl represented by R
1
, A
1
and A
2
, for example, there are phenylmethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, &agr;-naphthylmethyl, &bgr;-naphthylmethyl, and the like.
As the C
1-9
heteroaryl of the optionally substituted C
1-9
heteroaryl represented by R
1
, A
1
and A
2
, for example, there are 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 3-pyridazinyl, 4-pyridazinyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 1-(1,2,4-triazolyl), 3-(1,2,4-triazolyl), 4-(1,2,4-triazolyl), 2-benzothienyl, 3-benzothienyl, benzothiazol-2-yl, 2-quinolinyl, and the like.
As the C
2-19
heteroarylalkyl of the optionally substituted C
2-19
heteroarylalkyl represented by R
1
, A
1
and A
2
, for example, there are 2-pyridylmethyl, 4-pyridylmethyl, 2-pyrimidinylmethyl, 4-pyrimidinylmethyl, 3-pyrazolylmethyl, 2-thiazolylmenthyl, 2-imidazolylmethyl, 3-(1,2,4-triazolyl)methyl, 2-quinolinylmethyl, and the like.
As the substituents of the optionally substituted C
1-10
alkyl, optionally substituted C
2-10
alkenyl, optionally substituted C
2-10
alkynyl, optionally substituted C
3-10
cycloalkyl, optionally substituted C
4-20
cycloalkylalkyl, optionally substituted C
5-10
cycloalkenyl, optionally substituted C
6-20
cycloalkenylalkyl, optionally substituted C
6-10
aryl, optionally substituted C
7-20
arylalkyl, optionally substituted C
1-9
heteroaryl, or optionally substituted C
2-19
heteroarylalkyl represented by R
1
, A
1
and A
2
, for example, there are:
halogen (chlorine, bromine, fluorine, etc.);
C
1-10
alkyl (e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, 1-methylpropyl, pentyl, 1-methylbutyl, 1-ethylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, hexyl, 1-methylpentyl, 1-ethylpent yl, 3,3-dimethylbutyl, heptyl, 3,7-dimethyloctyl, etc.);
C
3-20
trialkylsilyl (e.g. , trimethyls

Affiliated with

Also associated with

Rating

Triazolone derivatives, use thereof, and intermediates therefor does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Triazolone derivatives, use thereof, and intermediates therefor, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Triazolone derivatives, use thereof, and intermediates therefor will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2918972