Phenylacetylene derivatives and agricultural/horticultural...

Details Phenylacetylene derivatives and agricultural/horticultural... Phenylacetylene derivatives and agricultural/horticultural...

2000-12-04

2001-11-06

Vollano, Jean F. (Department: 1621)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C560S024000, C556S420000, C564S056000

Reexamination Certificate

active

06313071

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a novel phenylacetylene derivative and an agricultural/horticultural fungicide containing the same as the active ingredient.
BACKGROUND ART
Heretofore, many carbamic acid derivatives have been reported, but it has not been known that a carbamic acid derivative having a phenylacetylene group as the compound of the present invention has excellent fungicidal activities.
The object of the present invention is to provide a novel phenylacetylene derivative and an agricultural/horticultural fungicide containing the same as the active ingredient.
The present inventors have conducted an extensive study to produce a novel agricultural/horticultural fungicide and, as a result, have found that the phenylacetylene derivative of the present invention (hereinafter referred to as the compound of the present invention) is a novel compound not disclosed in literatures and exhibits remarkable effects as an agricultural/horticultural fungicide, and have finally accomplished the present invention.
DISCLOSURE OF THE INVENTION
Namely, the present invention provides a phenylacetylene derivative represented by the general formula [I]:
{wherein X is a halogen atom, a C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group, a C
1
-C
6
haloalkyl group or a C
1
-C
6
haloalkoxy group, n is 0 or an integer of from 1 to 4, R
1
is a C
1
-C
6
alkyl group, R
2
is a hydrogen atom, a C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group, a C
2
-C
6
alkynyl group, a C
1
-C
6
alkoxy group, a C
1
-C
6
alkoxy C
1
-C
6
alkyl group, a C
1
-C
6
alkylcarbonyl group or a C
1
-C
6
alkoxycarbonyl group, A is a C
1
-C
6
alkylene group which may be branched, G is an oxygen atom, a sulfur atom or a —NR
3
— group [R
3
is a hydrogen atom or a C
1
-C
6
alkyl group], and Y is a hydrogen atom, a C
1
-C
6
alkyl group [said group may be substituted by a halogen atom, a hydroxyl group, a phenyl group or a C
1
-C
6
alkoxy group], a C
2
-C
10
alkenyl group, a C
2
-C
10
alkynyl group, a C
3
-C
6
cycloalkyl group [said group may be substituted by a halogen atom, a hydroxyl group or a C
1
-C
6
alkoxy group], a C
3
-C
6
cycloalkenyl group, a C
3
-C
6
cycloalkyl-C
1
-C
6
alkyl group, an aryl-C
1
-C
6
alkyl group [said group may be substituted by a halogen atom, a C
1
-C
6
alkyl group or a C
1
-C
6
alkoxy group], C(O)R
4
, COOR
5
, or a SiR
6
R
7
R
8
group [R
4
to R
8
are the same or different and represent a hydrogen atom or a C
1
-C
6
alkyl group]}; an agricultural/horticultural fungicide containing the same as the active ingredient; and a method for controlling an agricultural/horticultural plant disease, which employs a fungicidally effective amount thereof.
Symbols and terms used in this specification will be explained.
The halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
A notation such as C
1
-C
10
indicates that the carbon number of a substituent following this notation is from 1 to 10 in this case.
The C
1
-C
6
alkyl group represents a straight chain or branched chain alkyl group and may, for example, be a group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 1,1-dimethylpropyl or 1,1-dimethylbutyl.
The C
1
-C
10
alkyl group may, for example, be the above-mentioned alkyl group, or a group such as heptyl, octyl, 1,1-diethylbutyl, nonyl or decyl.
The C
3
-C
6
cycloalkyl group may, for example, be a group such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
The C
3
-C
6
cycloalkenyl group may, for example, be a group such as 1-cyclopenten-1-yl, 2-cyclopenten-1-yl, 1-cyclohexen-1-yl or 2-cyclohexen-1-yl.
The C
1
-C
6
haloalkyl group represents a straight chain or branched chain alkyl group substituted by a halogen atom and may, for example, be a group such as fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl or pentafluoroethyl.
The C
2
-C
10
alkenyl group represents a straight chain or branched chain alkenyl group and may, for example, be a group such as vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 1-hexenyl or 1-octenyl.
The C
2
-C
10
alkynyl group represents a straight chain or branched chain alkynyl group and may, for example, be a group such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 4-methyl-1-pentynyl or 3-methyl-1-pentynyl.
The C
1
-C
6
alkoxy group represents an alkyloxy group wherein the alkyl moiety has the above-mentioned meaning.
The C
1
-C
6
haloalkoxy group represents a haloalkyloxy group wherein the haloalkyl moiety has the above-mentioned meaning.
The C
1
-C
6
alkylcarbonyl group represents an alkylcarbonyl group wherein the alkyl moiety has the above-mentioned meaning.
The C
1
-C
6
alkoxycarbonyl group represents an alkoxycarbonyl group wherein the alkoxy moiety has the above-mentioned meaning.
The C
1
-C
6
alkylene group which may be branched, may, for example, be a group such as —CH
2
—, —CH(CH
3
)—, —C(CH
3
)
2
—, —CH
2
CH
2
— or —CH
2
CH
2
CH
2
—.
The aryl C
1
-C
6
alkyl group may, for example, be a group such as a benzyl group.
Now, specific examples of the compound of the present invention represented by the general formula [I] will be disclosed in Tables 1 to 52. However, the compound of the present invention is not limited to such compounds. Further, the compound numbers will be referred to in the subsequent description.
Symbols in the Tables have the following meanings respectively. Me represents a methyl group, Et represents an ethyl group, Pr represents a n-propyl group, Pr-i represents an isopropyl group, Bu represents a n-butyl group, Bu-i represents an isobutyl group, Bu-s represents a sec-butyl group, Bu-t represents a tert-butyl group, C
3
H
5
-c represents a cyclopropyl group, C
5
H
9
-c represents a cyclopentyl group, C
6
H
11
-c represents a cyclohexyl group, and Ph represents a phenyl group.
TABLE 1

Compound
m.p.
No.
X
1
X
2
X
3
X
4
Y
G
R
1
R
2
(° C.)
1-1
H
H
H
H
H
O
Me
H
1-2
H
H
H
H
Me
O
Me
H
1-3
H
H
H
H
Et
O
Me
H
1-4
H
H
H
H
Pr-i
O
Me
H
1-5
H
H
H
H
Bu
O
Me
H
1-6
H
H
H
H
Bu-i
O
Me
H
1-7
H
H
H
H
Bu-t
O
Me
H
Oily
1-8
H
H
H
H
C
5
H
11
O
Me
H
1-9
H
H
H
H
CHMePr
O
Me
H
1-10
H
H
H
H
C
6
H
13
O
Me
H
1-11
H
H
H
H
C
5
H
9
-c
O
Me
H
1-12
H
H
H
H
CH═CH
2
O
Me
H
1-13
H
H
H
H
C(Me)═CH
2
O
Me
H
1-14
H
H
H
H
C(Me)═CHMe
O
Me
H
1-15
H
H
H
H
CH
2
C≡CEt
O
Me
H
1-16
H
H
H
H
CHClMe
O
Me
H
1-17
H
H
H
H
CHClEt
O
Me
H
1-18
H
H
H
H
CHClPr
O
Me
H
1-19
H
H
H
H
CH
2
CHClMe
O
Me
H
1-20
H
H
H
H
CClMe
2
O
Me
H
1-21
H
H
H
H
CClMeEt
O
Me
H
1-22
H
H
H
H
CClMePr
O
Me
H
1-23
H
H
H
H
CClMePh
O
Me
H
1-24
H
H
H
H
CH(OMe)Me
O
Me
H
1-25
H
H
H
H
CH(OMe)Pr
O
Me
H
1-26
H
H
H
H
CH
2
CH(OMe)Me
O
Me
H
1-27
H
H
H
H
C(OMe)Me
2
O
Me
H
1-28
H
H
H
H
C(OMe)MeEt
O
Me
H
1-29
H
H
H
H
C(OMe)MePr
O
Me
H
TABLE 2
Com-
pound
m.p.
No.
X
1
X
2
X
3
X
4
Y
G
R
1
R
2
(° C.)
1-30
H
H
H
H
C(OMe)MeBu-t
O
Me
H
1-31
H
H
H
H
SiMe
3
O
Me
H
Oily
1-32
H
H
H
H
SiEt
3
O
Me
H
1-33
H
H
H
H
CH
2
Ph
O
Me
H
1-34
H
H
H
H
CF
3
O
Me
H
1-35
H
H
H
F
H
O
Me
H
102-104
1-36
H
H
H
F
Me
O
Me
H
75-78
1-37
H
H
H
F
Et
O
Me
H
1-38
H
H
H
F
Pr
O
Me
H
1-39
H
H
H
F
Pr-i
O
Me
H
1-40
H
H
H
F
Bu
O
Me
H
1-41
H
H
H
F
Bu-i
O
Me
H
1-42
H
H
H
F
Bu-s
O
Me
H
1-43
H
H
H
F
Bu-t
O
Me
H
102-105
1-44
H
H
H
F
C
5
H
11
O
Me
H
1-45
H
H
H
F
CHMePr
O
Me
H
1-46
H
H
H
F
CH
2
CH
2
CH
2
Pr-i
O
Me
H
1-47
H
H
H
F
CH
2
CHMeEt
O
Me
H
1-48
H
H
H
F
C
6
H
13
O
Me
H
1-49
H
H
H
F
C
7
H
15
O
Me
H
1-50
H
H
H
F
C
8
H
17
O
Me
H
1-51
H
H
H
F
C
9
H
19
O
Me
H
1-52
H
H
H
F
C
10
H
21
O
Me
H
1-53
H
H
H
F
C
3
H
5
-c
O
Me
H
1-54
H
H
H
F
C
5
H
9
-c
O
Me
H
72-75
1-55
H
H
H
F
C
6
H
11
-c
O
Me
H
1-56
H
H
H
F
CH
2
—C
5
H
9
-c
O
Me
H
1-57
H
H
H
F
CH
2
—C
6
H
11
-c
O
Me
H
1-58
H
H
H
F
CH═CH
2
O
Me
H
80-83
1-59
H
H
H
F
C(Me)═CH
2
O
Me
H
1-60
H
H
H
F
C(Me)═CHMe
O
Me
H
Oily
TABLE 3
Com-
pound
m.p.
No.
X
1
X
2
X
3
X
4
Y
G
R
1
R
2
(° C.)
1-61
H
H
H
F
CH
2
CH═CH
2
O
Me
H
1-62
H
H
H
F
CH
2
C≡CEt
O
Me
H

1-63
H
H
H
F
O
Me
H

1-64
H
H
H
F
CH(OH)Me
O
Me
H
Oily

Affiliated with

Also associated with

Rating

Phenylacetylene derivatives and agricultural/horticultural... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Phenylacetylene derivatives and agricultural/horticultural..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phenylacetylene derivatives and agricultural/horticultural... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2617696