US4397864A
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US
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2-Arylpropyl ether or thioether derivatives and insecticidal and acaricidal agents containing said derivatives
Assignee: Mitsui Chemicals Inc
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Filing: 1981-04-14
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Granted: 1983-08-09
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Expires: 2001-04-14
Abstract
Abstract The present invention relates to 2-arylpropyl ether or thioether derivatives represented by the following general formula [I]: <IMAGE> [I] wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: <IMAGE> [II] or the following general formula [III]: <IMAGE> [III] wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R1 may be the same or different, and also to processes for the preparation or these ethers of thioethers and a use of these ethers or thioethers. These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.
Inventors
- 👤 Kiyoshi Nakatani
- 👤 Satoshi Numata
- 👤 Tsuneo Inoue
- 👤 Kenji Kodaka
- 👤 Tsutomu Ishii
- 👤 Teruhiko Toyama
- 👤 Hajime Tachibana
- 👤 Takatoshi Udagawa
- 👤 Masatoshi Gohbara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 19:28
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/093; C07C17/10; C07C17/14; A; A01; A01N; A01N31/00; A01N31/04; A01N31/08; A01N31/14; A01N31/16; A01N33/00; A01N33/16; A01N33/18; A01N33/20; A01N35/00; A01N35/04; A01N37/00; A01N37/36; A01N37/38; A01N43/00; A01N43/02; A01N43/04; A01N43/06; A01N43/08; A01N43/24; A01N43/26; A01N43/28; A01N43/30; A01N47/00; A01N47/02; C07C17/35; C07C323/00; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/17; C07C43/174; C07C43/20; C07C43/257; C07C43/263; C07C43/267; C07C43/29; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C49/00; C07C49/76; C07C49/84; C07C57/00; C07C57/30; C07C59/00; C07C59/40; C07C59/58; C07C59/64; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
198 words
A 2-arylpropyl ether or thioether derivative represented by the following formula (I): ##STR237## wherein Ar stands for an aryl group selected from the group consisting of phenyl, naphthyl, anthryl and phenanthryl groups, which may be unsubstituted or substituted with the same or different substituents selected from the group consisting of a halogen atom; an alkyl, haloalkyl, phenyl, alkoxy, haloalkoxy, cycloalkoxy, phenoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxyalkyl, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkylsulfoxyl, acyl, alkoxyalkoxy, alkenylthio, alkoxycarbonyl, haloalkoxycarbonyl, alkynyloxycarbonyl, alkenyloxycarbonyl, nitro, nitrile, haloalkenylthio, methylenedioxy, 3,4-difluoromethylenedioxy, 3,4-difluoroethylenedioxy, or 3,4-trifluoroethylenedioxy group; and a polymethylene group having 3 to 5 carbon atoms, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR238## or the following formula (III): ##STR239## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same or different.
Claim 2
Dependent Claim
198 words
A 2-arylpropyl ether or thioether derivative represented by the following formula (I): ##STR237## wherein Ar stands for an aryl group selected from the group consisting of phenyl, naphthyl, anthryl and phenanthryl groups, which may be unsubstituted or substituted with the same or different substituents selected from the group consisting of a halogen atom; an alkyl, haloalkyl, phenyl, alkoxy, haloalkoxy, cycloalkoxy, phenoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxyalkyl, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkylsulfoxyl, acyl, alkoxyalkoxy, alkenylthio, alkoxycarbonyl, haloalkoxycarbonyl, alkynyloxycarbonyl, alkenyloxycarbonyl, nitro, nitrile, haloalkenylthio, methylenedioxy, 3,4-difluoromethylenedioxy, 3,4-difluoroethylenedioxy, or 3,4-trifluoroethylenedioxy group; and a polymethylene group having 3 to 5 carbon atoms, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR238## or the following formula (III): ##STR239## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same or different.
Claim 3
Dependent Claim
183 words
A 2-arylpropyl ether or thioether derivative represented by the following formula (I): ##STR240## wherein Ar stands for an aryl group selected from the group consisting of phenyl and naphthyl groups which may be unsubstituted or substituted with the same or different substituents selected from the group consisting of a halogen atom and an alkyl, haloalkyl, phenyl, alkoxy, haloalkoxy, cycloalkoxy, phenoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxyalkyl, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, acyl, alkoxyalkoxy, alkenylthio, alkoxycarbonyl, haloalkoxycarbonyl, alkynyloxycarbonyl, alkenyloxycarbonyl, nitro, nitrile, haloalkenylthio, or methylenedioxy group, R stands for a methyl or ethyl group Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR241## or the following formula (III): ##STR242## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same of different.
Claim 4
Dependent Claim
183 words
A 2-arylpropyl ether or thioether derivative represented by the following formula (I): ##STR240## wherein Ar stands for an aryl group selected from the group consisting of phenyl and naphthyl groups which may be unsubstituted or substituted with the same or different substituents selected from the group consisting of a halogen atom and an alkyl, haloalkyl, phenyl, alkoxy, haloalkoxy, cycloalkoxy, phenoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxyalkyl, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, acyl, alkoxyalkoxy, alkenylthio, alkoxycarbonyl, haloalkoxycarbonyl, alkynyloxycarbonyl, alkenyloxycarbonyl, nitro, nitrile, haloalkenylthio, or methylenedioxy group, R stands for a methyl or ethyl group Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR241## or the following formula (III): ##STR242## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same of different.
Claim 5
Dependent Claim
183 words
A 2-arylpropyl ether or thioether derivative represented by the following formula (I): ##STR243## wherein Ar is represented by the following formula (IV): ##STR244## wherein R 2 stands for a hydrogen or halogen atom, a lower alkyl or lower haloalkyl or lower alkoxy or lower haloalkoxy or methylenedioxy or lower alkylthio or nitrile or nitro group, and p is an integer of from 1 to 5, with the proviso that when p is 2 or more, groups R 2 may be the same or different, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR245## or the following formula (III): ##STR246## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same or different.
Claim 6
Dependent Claim
183 words
A 2-arylpropyl ether or thioether derivative represented by the following formula (I): ##STR243## wherein Ar is represented by the following formula (IV): ##STR244## wherein R 2 stands for a hydrogen or halogen atom, a lower alkyl or lower haloalkyl or lower alkoxy or lower haloalkoxy or methylenedioxy or lower alkylthio or nitrile or nitro group, and p is an integer of from 1 to 5, with the proviso that when p is 2 or more, groups R 2 may be the same or different, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR245## or the following formula (III): ##STR246## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same or different.
Claim 7
Dependent Claim
27 words
A 2-arylpropyl ether or thioether derivative as set forth in one of claims 1, 2 or 3, wherein R in the formula (I) is a methyl group.
Claim 8
Dependent Claim
33 words
A 2-arylpropyl ether or thioether derivative as set forth in claim 3, wherein R 2 in the formula (IV) is a halogen atom or a lower alkoxy group or a lower haloalkoxy group.
Claim 9
Dependent Claim
27 words
A 2-arylpropyl ether or thioether derivative as set forth in one of claims 1, 2 or 3, wherein Y in the formula (I) is an oxygen atom.
Claim 10
Dependent Claim
31 words
A 2-arylpropyl ether or thioether derivative as set forth in one of claims 1, 2 or 3, wherein Z in the formula (III) in the formula (I) is an oxygen atom.
Claim 11
Dependent Claim
34 words
A 2-arylpropyl ether or thioether derivative as set forth in one of claims 1, 2 or 3, wherein R 1 in the formula (III) in the formula (I) is a hydrogen or halogen atom.
Claim 12
Dependent Claim
31 words
A 2-arylpropyl ether or thioether derivative as set forth in one of claims 1, 2 or 3 wherein said group B is a group of the formula (III) as previously defined.
Claim 13
Dependent Claim
229 words
An insecticidal and acaricidal composition, comprising a carrier or vehicle and, as an active ingredient, an insecticidally or acaricidally effective amount of at least one member selected from the group consisting of 2-arylpropyl ether and thioether derivatives represented by the following formula (I): ##STR247## wherein Ar stands for an aryl group selected from the group consisting of phenyl, naphthyl, anthryl and phenanthryl groups, which may be unsubstituted or substituted with the same or different substituents selected from the group consisting of a halogen atom; an alkyl, haloalkyl, phenyl, alkoxy, haloalkoxy, cycloalkoxy, phenoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxyalkyl, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkylsulfoxyl, acyl, alkoxyalkoxy, alkenylthio, alkoxycarbonyl, haloalkoxycarbonyl, alkynyloxycarbonyl, alkenyloxycarbonyl, nitro, nitrile, haloalkenylthio, methylenedioxy, 3,4-difluoromethylenedioxy, 3,4-difluoroethylenedioxy, or 3,4-trifluoroethylenedioxy group; and a polymethylene group having 3 to 5 carbon atoms, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR248## or the following formula (III): ##STR249## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same or different.
Claim 14
Dependent Claim
229 words
An insecticidal and acaricidal composition, comprising a carrier or vehicle and, as an active ingredient, an insecticidally or acaricidally effective amount of at least one member selected from the group consisting of 2-arylpropyl ether and thioether derivatives represented by the following formula (I): ##STR247## wherein Ar stands for an aryl group selected from the group consisting of phenyl, naphthyl, anthryl and phenanthryl groups, which may be unsubstituted or substituted with the same or different substituents selected from the group consisting of a halogen atom; an alkyl, haloalkyl, phenyl, alkoxy, haloalkoxy, cycloalkoxy, phenoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxyalkyl, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkylsulfoxyl, acyl, alkoxyalkoxy, alkenylthio, alkoxycarbonyl, haloalkoxycarbonyl, alkynyloxycarbonyl, alkenyloxycarbonyl, nitro, nitrile, haloalkenylthio, methylenedioxy, 3,4-difluoromethylenedioxy, 3,4-difluoroethylenedioxy, or 3,4-trifluoroethylenedioxy group; and a polymethylene group having 3 to 5 carbon atoms, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR248## or the following formula (III): ##STR249## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same or different.
Claim 15
Dependent Claim
214 words
An insecticidal and acaricidal composition, comprising a carrier or vehicle and, as an active ingredient, an insecticidally or acaricidally effective amount of at least one member selected from the group consisting of 2-arylpropyl ether and thioether derivatives represented by the following formula (I): ##STR250## wherein Ar stands for an aryl group selected from the group consisting of phenyl and naphthyl groups which may be unsubstituted or substituted with the same or different substituents selected from the group consisting of a halogen atom and an alkyl, haloalkyl, phenyl, alkoxy, haloalkoxy, cycloalkoxy, phenoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxyalkyl, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, acyl, alkoxyalkoxy, alkenylthio, alkoxycarbonyl, haloalkoxycarbonyl, alkynyloxycarbonyl, alkenyloxycarbonyl, nitro, nitrile, haloalkenylthio, or methenedioxy group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR251## or the following formula (III): ##STR252## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same or different.
Claim 16
Dependent Claim
214 words
An insecticidal and acaricidal composition, comprising a carrier or vehicle and, as an active ingredient, an insecticidally or acaricidally effective amount of at least one member selected from the group consisting of 2-arylpropyl ether and thioether derivatives represented by the following formula (I): ##STR250## wherein Ar stands for an aryl group selected from the group consisting of phenyl and naphthyl groups which may be unsubstituted or substituted with the same or different substituents selected from the group consisting of a halogen atom and an alkyl, haloalkyl, phenyl, alkoxy, haloalkoxy, cycloalkoxy, phenoxy, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxyalkyl, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, acyl, alkoxyalkoxy, alkenylthio, alkoxycarbonyl, haloalkoxycarbonyl, alkynyloxycarbonyl, alkenyloxycarbonyl, nitro, nitrile, haloalkenylthio, or methenedioxy group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR251## or the following formula (III): ##STR252## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same or different.
Claim 17
Dependent Claim
214 words
An insecticidal and acaricidal composition, comprising a carrier or vehicle and, as an active ingredient, an insecticidally or acaricidally effective amount of at least one member selected from the group consisting of 2-arylpropyl ether and thioether derivatives represented by the following formula (I): ##STR253## wherein Ar is represented by the following formula (IV): ##STR254## wherein R 2 stands for a hydrogen or halogen atom, a lower alkyl or lower haloalkyl or lower alkoxy or lower haloalkoxy or methylenedioxy or lower alkylthio or nitrile or nitro group, and p is an integer of from 1 to 5, with the proviso that when p is 2 or more, groups R 2 may be the same or different, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR255## or the following formula (III): ##STR256## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same or different.
Claim 18
Dependent Claim
214 words
An insecticidal and acaricidal composition, comprising a carrier or vehicle and, as an active ingredient, an insecticidally or acaricidally effective amount of at least one member selected from the group consisting of 2-arylpropyl ether and thioether derivatives represented by the following formula (I): ##STR253## wherein Ar is represented by the following formula (IV): ##STR254## wherein R 2 stands for a hydrogen or halogen atom, a lower alkyl or lower haloalkyl or lower alkoxy or lower haloalkoxy or methylenedioxy or lower alkylthio or nitrile or nitro group, and p is an integer of from 1 to 5, with the proviso that when p is 2 or more, groups R 2 may be the same or different, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula (II): ##STR255## or the following formula (III): ##STR256## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R 1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R 1 may be the same or different.
Claim 19
Dependent Claim
30 words
An insecticidal or acaricidal agent in accordance with one of claims 10, 11 or 12, wherein said active ingredient is present in an amount of 0.001 to 95% by weight.
Claim 20
Dependent Claim
30 words
An insecticidal or acaricidal agent in accordance with one of claims 10, 11 or 12, wherein said active ingredient is present in an amount of 0.01 to 50% by weight.
Claim 21
Independent Claim
33 words
A method of combatting insect pests and/or acarids comprising contacting the insect pests or acarids with a pesticidally effective amount of a compound in accordance with one of claims 1, 2 or 3.
Claim 22
Independent Claim
33 words
A method of combatting insect pests and/or acarids comprising contacting the insect pests or acarids with a pesticidally effective amount of a composition in accordance with one of claims 10, 11 or 12.
References Cited (Backward Citations)
US4073812A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-08-08 | 1987-02-07 | 1987-08-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-08-08 | 1991-02-07 | 1991-08-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-08-08 | 1995-02-07 | 1995-08-09 | $7700.00 | Window Closed / Lapsed |