3-arylphenyl sulfide derivative and insecticide and miticide

Details 3-arylphenyl sulfide derivative and insecticide and miticide 3-arylphenyl sulfide derivative and insecticide and miticide

2000-10-27

2003-01-21

Shah, Mukund J. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S222200, C514S228800, C514S241000, C514S252010, C514S252100, C514S256000, C514S277000, C514S709000, C544S003000, C544S063000, C544S179000, C544S180000, C544S239000, C544S242000, C544S298000, C544S336000, C546S243000, C562S045000

Reexamination Certificate

active

06509354

ABSTRACT:

TECHNICAL FIELD
The present invention relates to novel 3-arylphenyl sulfide derivatives and insecticides and miticides containing them as an active ingredient.
BACKGROUND ART
East German Patent No. 142541, East German Patent No. 142542, JP-A-7-2655 and Tetrahedron vol. 39, p.2289 (1983) and Tetrahedron Lett. vol. 25, 44, p.5095 (1984) disclose 3-methylthiobiphenyl derivatives, and East German Patent No. 4323916 and International Patent Application WO95/02580 disclose 3-pyridylphenyl sulfide derivatives. However, none of them mention anything about insecticides or miticides. Also, International Patent Application WO96/06830, JP-A-2-184675, JP-A-60-233061, European Patent No. 152590, South African Patent No. 6800955 and German Patent No. 3316300 report 3-azorylphenyl sulfide derivatives but mention nothing about insecticides or miticides. On the other hand, use of 4-biphenyl sulfide derivatives as insecticides is reported, for example, in U.S. Pat. No. 3442955. However, the 3-arylphenyl sulfide derivatives of the present invention have not been known yet.
In recent years, some of the conventional commercial insecticides are restricted in their use in view of problems of persistency, accumulation and environmental pollution, and others have become less effective as the pest insects have acquired resistance during their use for a long period of time. Therefore, it has been desired to develop a new insecticide which is highly effective at a low dose and excellent in safety.
DISCLOSURE OF THE INVENTION
Under these circumstances, the present inventors have synthesized various 3-arylphenyl sulfide derivatives and have studied their physiological activities. As a result, it has been found that the compounds of the present invention exhibit outstanding effects on various pests, especially on farm and garden pests including mites represented by two-spotted spider mite, Kanzawa spider mite and citrus red mite, pest lepidopterans represented by diamondblackmoss, Asiatic rice borer and beat armyworm, pest hemipterans represented by brown rice planthopper, green rice leafhopper and cotton aphid and pest coleoptera represented by adzuki bean weevil. The present invention has been accomplished on the basis of this discovery.
That is, the present invention provides (1) 3-arylphenyl sulfide derivatives represented by general formula (I):
{ wherein R is a C
2
-C
6
alkyl group (which may be mono- or poly-substituted by halogen atoms or cyano groups), a C
2
-C
6
alkenyl group (which may be mono- or poly-substituted by halogen atoms or cyano groups), a C
2
-C
6
alkynyl group (which may be mono- or poly-substituted by halogen atoms or cyano groups), a C
3
-C
6
cycloalkyl group (which may be mono- or poly-substituted by halogen atoms or cyano groups) or a C
4
-C
9
cycloalkylalkyl group (which may be mono- or poly-substituted by halogen atoms or cyano groups), n is an integer of from 0 to 2, Ar is a group represented by any one of general formulae:
wherein Q
1
, Q
2
, Q
3
, Q
4
and Q
5
are, respectively, a nitrogen atom or C-A
1
, a nitrogen atom or C-A
2
, a nitrogen atom or C-A
3
, a nitrogen atom or C-A
4
, and a nitrogen atom or C-A
5
, Q
6
is an oxygen atom or a sulfur atom, Q
7
is a nitrogen atom or C-A
7
, Q
8
is a nitrogen atom or C-A
8
, A
1
, A
5
, A
7
, A
11
and B
0
are hydrogen atoms ,halogen atoms, amino groups, cyano groups, nitro groups, C
1
-C
6
alkyl groups, C
1
-C
4
haloalkyl groups, C
1
-C
6
alkylthio groups (which may be mono- or poly-substituted by halogen atoms) or C
1
-C
6
alkoxy groups, A
2
, A
3
, A
4
, A
6
, A
9
, B
1
, B
2
and B
3
are hydrogen atoms, halogen atoms, cyano groups, nitro groups, C
1
-C
6
alkyl groups (which may be mono- or poly-substituted by halogen atoms, hydroxyl groups, cyano groups, C
2
-C
7
alkoxycarbonyl groups or C
1
-C
6
alkoxy groups), C
2
-C
6
alkenyl groups (which may be mono- or poly-substituted by halogen atoms or cyano groups), C
2
-C
6
alkynyl groups (which may be mono- or poly-substituted by halogen atoms or cyano groups), C
1
-C
6
alkoxy groups (which may be mono- or poly-substituted by halogen atoms, cyano groups, C
2
-C
5
alkoxycarbonyl groups or C
1
-C
3
alkoxy groups), C
1
-C
6
alkylthio groups (which may be mono- or poly-substituted by halogen atoms or C
1
-C
3
alkoxy groups), C
1
-C
6
alkylsulfinyl groups (which may be mono- or poly-substituted by halogen atoms or C
1
-C
3
alkoxy groups), C
1
-C
6
alkylsulfonyl groups (which may be mono- or poly-substituted by halogen atoms or C
1
-C
3
alkoxy groups), C
1
-C
7
acyl groups, C
2
-C
5
haloalkylcarbonyl groups, carboxyl groups, C
2
-C
7
alkoxycarbonyl groups or NR
1
R
2
[wherein R
1
and R
2
are independently hydrogen atoms, C
1
-C
6
alkyl groups (which may be mono- or poly-substituted by halogen atoms, cyano groups, hydroxyl groups, C
1
-C
6
alkoxy groups or C
1
-C
6
alkylthio groups), C
2
-C
6
alkenyl groups (which may be mono- or poly-substituted by halogen atoms or cyano groups), C
2
-C
6
alkynyl groups (which may be mono- or poly-substituted by halogen atoms or cyano groups), C
1
-C
7
acyl groups or C
2
-C
7
alkoxycarbonyl groups or may form a 5 to 6-membered ring together with the nitrogen atom attached thereto], A
8
is a hydrogen atom, a halogen atom, a cyano group, a C
1
-C
6
alkyl group (which may be mono- or poly-substituted by halogen atoms or C
1
-C
3
alkoxy groups), a C
1
-C
6
alkoxy group (which may be mono- or poly-substituted by halogen atoms or C
1
-C
3
alkoxy groups), a C
1
-C
7
acyl group, a C
2
-C
5
haloalkylcarbonyl group or NR
1
R
2
(wherein R
1
and R2 are the same as defined above), and A
10
is a hydrogen atom, a C
1
-C
6
alkyl group (which may be mono- or poly-substituted by halogen atoms or C
1
-C
3
alkoxy groups), a C
1
-C
7
acyl group, a C
2
-C
5
haloalkylcarbonyl group, a carboxyl group or a C
2
-C
7
alkoxycarbonyl group; provided that when Ar is represented by general formula (Ar-1) or (Ar-2), not more than three of Q
1
-Q
5
are nitrogen atoms; when Ar is represented by general formula (Ar-1) wherein only Q
5
is a nitrogen atom, A
1
is a hydrogen atom; when Ar is represented by general formula (Ar-1) wherein Q
1
, Q
2
, Q
3
, Q
4
and Q
5
are, respectively, C-A
1
, C-A
2
, C-A
3
, C-A
4
and C-A
5
, A
21
A
3
, A
4
and B
2
are not simultaneously hydrogen atoms; when all of A
1
to A
5
are hydrogen atoms, compounds wherein B
2
is a methyl group, and R is an isopropyl are excluded; and when Ar is represented by general formula (Ar-4) wherein Q
8
is C-A
8
, R is a C
2
-C
6
alkyl group (which may be mono- or poly-substituted by halogen atoms), a C
3
-C
6
cycloalkyl group (which may be mono- or poly-substituted by halogen atoms) or a C
4
-C
9
cycloalkylalkyl group (which may be mono- or poly-substituted by halogen atoms)}, (2) insecticides or miticides containing these 3-arylphenyl sulfide derivatives as an active ingredient (3) a method of killing a farm or garden pest insect or mites which uses an effective amount of these 3-arylphenyl sulfide derivatives.
The terms used in this application are defined below.
The halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
The alkyl group means a linear or branched C
1-6
alkyl group such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group or a tert-butyl group, unless otherwise noted.
The cycloalkyl group means a C
3-6
cycloalkyl group such as a cyclopropyl group, a cyclopentyl group or a cyclohexyl group.
The cycloalkylalkyl group means a C
1-3
alkyl group substituted with a C
3-6
cycloalkyl group such as a cyclopropylmethyl group, a cyclopentylmethyl group or a cyclohexylmethyl group.
The alkenyl group means a linear or branched C
2-6
alkenyl group such as an ethenyl group or a 2-propenyl group.
The alkynyl group means a linear or branched C
2-6
alkynyl group such as an ethynyl group or a 2-propynyl group.
The haloalkyl group means a C
1-4
alkyl group substituted with from 1 to 9 identical or different halogen a

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