Acrylonitrile compounds

Details Acrylonitrile compounds Acrylonitrile compounds

2001-08-13

2003-11-04

Shah, Mukund J. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C546S210000, C546S275400, C514S326000, C514S406000, C514S365000, C514S341000, C548S255000, C548S204000, C544S140000

Reexamination Certificate

active

06642234

ABSTRACT:

TECHNICAL FIELD
The present invention relates to novel acrylonitrile compounds and agricultural chemicals containing said compounds as an active ingredient. The agricultural chemicals as referred to herein include insecticides, acaricides, nematocides, herbicides and fungicides, etc., and are especially insecticides, acaricides and nematocides in the field of agriculture, horticulture, stock farming and sanitation.
BACKGROUND ART
For acrylonitrile derivatives, WO97/40009 discloses the use thereof as agricultural chemicals.
With the long-term use of insecticides and fungicides, recently, some pests have become resistant to chemicals and are often difficult to exterminate with conventional insecticides and fungicides. Accordingly, it is an object of the present invention to provide novel insecticides and fungicides exhibiting excellent pesticidal activities.
DISCLOSURE OF THE INVENTION
In order to solve the above-mentioned problems, the present inventors have studied to develop compounds described below that exhibit excellent pesticidal activities, in particular exhibit the activities for extremely long term. Consequently, the inventors have completed the present invention.
Specifically, the present invention relates to compounds described in the following [1] to [11] (hereinafter referred to as compounds of the present invention) and agricultural chemicals containing said compounds as an active ingredient described in the following [12].
[11] Acrylonitrile compounds of formula (1):
[wherein, R is a C
1
-C
6
alkyl, a C
3
-C
7
cycloalkyl optionally substituted by a C
1
-C
4
alkyl, a phenyl optionally substituted by X, a naphthyl or a pyridyl, R
1
is H, a halogen, a C
1
-C
6
alkyl, a C
3
-C
7
cycloalkyl optionally substituted by a C
1
-C
4
alkyl, a C
1
-C
6
alkoxy, a C
1
-C
4
haloalkyl, a C
2
-C
6
alkoxyalkyl, CH
3
OC
2
H
4
OCH
2
, a C
2
-C
6
alkylsulfenylalkyl, a C
2
-C
6
alkylsulfinylalkyl, a C
2
-C
6
alkylsulfonylalkyl, a C
1
-C
3
alkyl substituted by phenyl, a phenyl, C
7
-C
10
phenoxyalkyl, COORa, CONHRb, CONRaRb, CORa, CO(piperidyl), CN, NO
2
or CH
2
J,
A is
B is H, a C
1
-C
4
alkyl, a C
2
-C
4
alkoxyalkyl, CH
2
SCH
3
, CH
2
OC
2
H
4
OCH
3
, a C
1
-C
4
alkyl substituted by Rc or Rd, a tetrahydropyranyl, Si(CH
3
)
3
, SO
2
Re, SO
2
NHRb, SO
2
NRaRb, C(S)NHRb, C(S)NRaRb, CH
2
COORa, C(O)Rf, P(O)RgRh, P(S)RgRh, an alkali metal, an alkaline earth metal or NHRiRjRk,
X is one to three substituents as freely selected from a halogen, a C
1
-C
4
alkyl, a C
1
-C
4
haloalkyl, a C
1
-C
4
alkoxy, a C
1
-C
4
haloalkoxy, a C
1
-C
4
alkylsulfenyl, a C
1
-C
4
alkylsulfinyl, a C
1
-C
4
alkylsulfonyl, a C
1
-C
4
haloalkylsulfenyl, a C
1
-C
4
haloalkylsulfinyl, a C
1
-C
4
haloalkylsulfonyl, NO
2
, CN, a phenyl and a phenoxy, Y, Y
1
and Y
2
are each independently of the other H, a halogen, a C
1
-C
4
alkyl, a C
1
-C
4
haloalkyl, a C
1
-C
4
alkoxy, a C
1
-C
4
haloalkoxy, a C
1
-C
4
alkylsulfenyl, a C
1
-C
4
alkylsulfinyl, a C
1
-C
4
alkylsulfonyl, a C
1
-C
4
haloalkylsulfenyl, a C
1
-C
4
haloalkylsulfinyl, a C
1
-C
4
haloalkylsulfonyl, NO
2
or CN,
Y
3
is a C
1
-C
4
alkyl or a C
1
-C
4
haloalkyl,
Ra is a C
1
-C
6
alkyl,
Rb is H, a C
1
-C
6
alkyl, or a phenyl optionally substituted by T
1
,
Rc is a phenyl optionally substituted by one or more substituents as freely selected from a halogen, a C
1
-C
4
alkyl, a C
1
-C
4
alkoxy and a C
1
-C
4
haloalkyl,
Rd is a benzoyl optionally substituted by one or more substituents as freely selected from a halogen, a C
1
-C
4
alkyl and a C
1
-C
4
haloalkyl,
Re is a C
1
-C
4
alkyl, a C
1
-C
4
haloalkyl, or a phenyl optionally substituted by T
1
,
Rf is a C
1
-C
6
alkyl, a C
2
-C
6
alkenyl, a C
1
-C
6
haloalkyl, a C
2
-C
4
alkoxyalkyl, a C
3
-C
6
halocycloalkyl, a C
1
-C
4
alkyl substituted by Rc, a C
3
-C
7
cycloalkyl optionally substituted by a C
1
-C
4
alkyl, a cycloalkyl substituted by Rc, a cyclopropyl substituted by Rc and a C
1
-C
4
alkyl, a C
3
-C
4
cycloalkyl substituted by Rc and a halogen, a cyclopropyl substituted by T
2
and a C
1
-C
4
alkyl, a C
2
-C
4
alkenyl substituted by Rc, a C
1
-C
6
alkoxy, a C
1
-C
4
haloalkoxy, a C
2
-C
5
alkenyloxy, a C
3
-C
6
cycloalkoxy optionally substituted by a C
1
-C
3
alkyl, a benzyloxy, COORa, —NU
1
U
2
, a phenyl optionally substituted by T
3
, a naphthyl, a pyridyl optionally substituted by T
1
, a phenyl C
1
-C
6
alkyl or A-1 to A-151,
Rg and Rh are each independently of the other OH, a phenyl, a C
1
-C
6
alkyl, a C
1
-C
6
alkoxy or a C
1
-C
4
alkylsulfenyl,
Ri, Rj and Rk are each independently of the other H, a C
1
-C
6
alkyl, a C
1
-C
4
alkenyl, a C
3
-C
6
cycloalkyl optionally substituted by a C
1
-C
3
alkyl or a benzyl, or any two of Ri, Rj and Rk may, together with the nitrogen atom to which they are bonded, form a 5- to 8-membered ring group optionally containing an oxygen atom, a nitrogen atom or a sulfur atom,
J is a pyrazolyl, an imidazolyl or a morpholinyl,
T
1
is a halogen, a C
1
-C
4
alkyl, a C
1
-C
4
haloalkyl or a C
1
-C
4
alkoxy,
T
2
is a C
2
-C
4
alkenyl optionally substituted by a halogen,
T
3
is one to five substituents as freely selected from a halogen, a C
1
-C
4
alkyl, a C
1
-C
4
haloalkyl, a C
1
-C
4
alkoxy, a C
1
-C
4
haloalkoxy, a C
1
-C
4
alkylsulfenyl, a C
1
-C
4
alkylsulfinyl, a C
1
-C
4
alkylsulfonyl, a C
1
-C
4
haloalkylsulfenyl, a C
1
-C
4
haloalkylsulfinyl, a C
1
-C
4
haloalkylsulfonyl, NO
2
, CN, CHO, —NU
1
U
2
, a phenyl and a phenoxy,
U
1
and U
2
are each independently of the other H, a C
1
-C
6
alkyl, COORa, a phenyl or a benzyl, or U
1
and U
2
may, together with the nitrogen atom to which they are bonded, form a 5- to 8-membered ring group optionally containing an oxygen atom, a nitrogen atom or a sulfur atom,
m represents the number of substituents, and is 0, 1, 2 or 3,
n represents the number of substituents, and is 0, 1, 2, 3 or 4,
p represents the number of substituents, and is 0, 1 or 2,
q represents the number of substituents, and is 0 or 1,
(provided that when m, n or p is 2 or more, then the substituents may be the same or different)].
[2] Acrylonitrile compounds of the above-mentioned [1], in which A is
[3] Acrylonitrile compounds of the above-mentioned [2], in which R is
1-naphtyl, tertiary butyl or 2-pyridyl,
X
1
is H, a halogen, a C
1
-C
4
alkyl, a C
1
-C
4
alkoxy, a C
1
-C
4
haloalkyl or a phenyl,
X
2
is H or a halogen,
R
1
is H, a C
1
-C
6
alkyl, a C
3
-C
7
cycloalkyl, CN, COORa, CO(N-piperidyl), a C
2
-C
6
alkylsulfenylalkyl, a C
2
-C
6
alkoxyalkyl, CH
3
OC
2
H
4
OCH
2
, CONRaRb, a phenyl or CH
2
J,
A is A-1, A-2, A-3, A-6 or A-7,
B is H, a C
1
-C
4
alkyl, C(O)Rf, SO
2
Re or a C
2
-C
4
alkoxyalkyl,
Ra and Rb are each independently of the other a C
1
-C
6
alkyl,
Rf is a C
1
-C
6
alkyl, a C
1
-C
6
alkoxy, a phenyl optionally substituted by a halogen, 2-pyridyl, 3-pyridyl, a phenyl C
1
-C
6
alkyl or 5-pyrazolyl substituted by a C
1
-C
4
alkyl,
Re is a C
1
-C
4
alkyl or a phenyl,
Y
1
and Y
2
are each independently of the other H, a halogen, a C
1
-C
4
alkyl, a C
1
-C
4
haloalkyl or CN,
Y
3
is a C
1
-C
4
alkyl,
J is an N-pyrazolyl or N-morpholinyl.
[4] Acrylonitrile compounds of the above-mentioned [3], in which R is
X
1
is H, a halogen, a C
1
-C
4
alkyl, a C
1
-C
4
alkoxy, a C
1
-C
4
haloalkyl or a phenyl,
X
2
is H or a halogen,
R
1
is H, a C
1
-C
6
alkyl, a C
3
-C
7
cycloalkyl, CN, COORa, CO(N-piperidyl), a C
2
-C
6
alkylsulfenylalkyl, a C
2
-C
6
alkoxyalkyl, CH
3
OC
2
H
4
OCH
2
, CONRaRb, a phenyl or CH
2
J,
A is A-1,
B is H, a C
1
-C
4
alkyl, C(O)Rf, SO
2
Re or a C
2
-C
4
alkoxyalkyl,
Ra and Rb are each independently of the other a C
1
-C
6
alkyl,
Rf is a C
1
-C
6
alkyl, a C
1
-C
6
alkoxy, a phenyl substituted by a halogen, 2-pyridyl, 3-pyridyl, a phenyl C
1
-C
6
alkyl or 5-pyrazolyl substituted by a C
1
-C
4
alkyl,
Re is a C
1
-C
4
alkyl or a phenyl,
Y
1
is H, a halogen, a C
1
-C
4
alkyl or CN,
Y
2
is H, a

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