US4791123A
Expired / Lapsed
US
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Insecticidal triffluormethyl alkane derivatives
Assignee: Bayer Pharma AG
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Filing: 1987-01-22
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Granted: 1988-12-13
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Expires: 2007-01-22
Abstract
Abstract There are provided new alkane and alkoxyalkane derivatives of the general formula I ##STR1## in which R 1 , R 2 , R 3 , R 4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
Inventors
- 👤 Helga Franke
- 👤 Heinrich Franke
- 👤 Hans-Rudolf Kruger
- 👤 Hartmut Joppien
- 👤 Dietrich Baumert
- 👤 David Giles
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 18:44
CPC Classifications
C; C07; C07C; C07C43/00; C07C43/02; C07C43/257; C07C43/275; C07C43/29; A; A01; A01N; A01N29/00; A01N29/10; A01N31/00; A01N31/08; A01N31/14; A01N31/16; A01N33/00; A01N33/02; A01N33/06; A01N33/08; A01N33/10; A01N43/00; A01N43/02; A01N43/24; A01N43/26; A01N43/28; A01N43/30; A01N43/34; A01N43/40; A01N47/00; A01N47/02; C07C25/00; C07C25/18; C07C309/00; C07C43/20; C07C43/225; C07C45/00; C07C45/44; Y; Y10; Y10S; Y10S424/00; Y10S424/08
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
218 words
An alkane or alkoxyalkane derivative of the formula ##STR25## in which R 1 is aryl or heteroaryl or these groups substituted by C 1-4 alkyl, halo-C 1-4 alkyl, phenyl-C 1-4 alkyl, C 2-4 alkenyl, halo-C 2-4 alkenyl, phenyl-C 2-4 alkenyl, C 2-4 alkynyl, halo-C 2-4 alkynyl, phenyl-C 2-4 alkynyl, C 1-4 alkoxy, halo-C 1-4 alkoxy, phenyl-C 1-4 alkoxy, C 2-4 alkenyloxy, halo-C 2-4 alkenyloxy, phenyl-C 2-4 alkenyloxy, C 2-4 alkynyloxy, halo-C 2-4 akynyloxy, phenyl-C 2-4 alkynyloxy, alkylsulphonyloxy, haloalkylsulphonyloxy, arylsulphonyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C 1-4 alkyl-aryloxy, or nitroaryloxy, wherein heteroaryl is benzofuranyl, benzothiophenyl, benzoxazolyl, indanyl or benzodioxanyl R 2 is hydrogen or C 1-4 alkyl, R 3 is hydrogen, cyano or ethynyl, R 4 is phenyl or pyridyl or these groups substituted by at least one of C 1-6 alkyl, halo-C 1-6 alkyl, phenyl-C 1-6 alkyl, C 2-6 alkyl interrupted by an O-, N- or S-atom, C 2-4 alkenyl, halo-C 2-4 alkenyl, phenyl-C 2-4 alkenyl, C 1-4 alkoxy, halo-C 1-4 alkoxy, phenyl-C 1-4 alkoxy, C 2-4 alkenyloxy, halo-C 2-4 alkenyloxy, phenyl-C 2-4 alkenyloxy, C 2-4 alkynyloxy, halo-C 2-4 alkynyloxy, phenyl-C 2-4 alkynyloxy, aryloxy, haloaryloxy, C 1-4 alkylaryloxy, arylamino, haloarylamino, C 1-4 alkylarylamino, aryl-N-C 1-4 alkylamino, aryl-N-C 1-4 acylamino, aroyl, haloaroyl, C 1-4 alkylaroyl, aryl, haloaryl, C 1-4 alkylaryl or halo, and A is CH 2 or O.
Claim 2
Dependent Claim
218 words
An alkane or alkoxyalkane derivative of the formula ##STR25## in which R 1 is aryl or heteroaryl or these groups substituted by C 1-4 alkyl, halo-C 1-4 alkyl, phenyl-C 1-4 alkyl, C 2-4 alkenyl, halo-C 2-4 alkenyl, phenyl-C 2-4 alkenyl, C 2-4 alkynyl, halo-C 2-4 alkynyl, phenyl-C 2-4 alkynyl, C 1-4 alkoxy, halo-C 1-4 alkoxy, phenyl-C 1-4 alkoxy, C 2-4 alkenyloxy, halo-C 2-4 alkenyloxy, phenyl-C 2-4 alkenyloxy, C 2-4 alkynyloxy, halo-C 2-4 akynyloxy, phenyl-C 2-4 alkynyloxy, alkylsulphonyloxy, haloalkylsulphonyloxy, arylsulphonyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C 1-4 alkyl-aryloxy, or nitroaryloxy, wherein heteroaryl is benzofuranyl, benzothiophenyl, benzoxazolyl, indanyl or benzodioxanyl R 2 is hydrogen or C 1-4 alkyl, R 3 is hydrogen, cyano or ethynyl, R 4 is phenyl or pyridyl or these groups substituted by at least one of C 1-6 alkyl, halo-C 1-6 alkyl, phenyl-C 1-6 alkyl, C 2-6 alkyl interrupted by an O-, N- or S-atom, C 2-4 alkenyl, halo-C 2-4 alkenyl, phenyl-C 2-4 alkenyl, C 1-4 alkoxy, halo-C 1-4 alkoxy, phenyl-C 1-4 alkoxy, C 2-4 alkenyloxy, halo-C 2-4 alkenyloxy, phenyl-C 2-4 alkenyloxy, C 2-4 alkynyloxy, halo-C 2-4 alkynyloxy, phenyl-C 2-4 alkynyloxy, aryloxy, haloaryloxy, C 1-4 alkylaryloxy, arylamino, haloarylamino, C 1-4 alkylarylamino, aryl-N-C 1-4 alkylamino, aryl-N-C 1-4 acylamino, aroyl, haloaroyl, C 1-4 alkylaroyl, aryl, haloaryl, C 1-4 alkylaryl or halo, and A is CH 2 or O.
Claim 3
Dependent Claim
47 words
Alkane or alkoxyalkane derivative according to claim 1, in which R 1 is chlorophenyl, bromophenyl, fluorophenyl, methylphenyl, methoxyphenyl, ethoxyphenyl, difluoromethoxyphenyl, fluoroethoxyphenyl, or trifluoroethoxyphenyl, R 2 is hydrogen or methyl, R 3 is hydrogen, R 4 is phenoxyphenyl, fluorophenoxyphenyl or phenoxypyridyl and A is CH 2 or O.
Claim 4
Dependent Claim
19 words
Insecticidal and acaricidal composition which comprises a compound claimed in claim 1 in admixture with an agriculturally acceptable diluent.
Claim 5
Dependent Claim
28 words
A method of combating insects and acarids which comprises applying to the insects or acarids or their locus an effective amount of a compound claimed in claim 1.
Claim 6
Dependent Claim
18 words
The method of claim 4 in which said compound is [2-(4-ethoxyphenyl)-2-trifluoromethylpropyl](4-fluoro-3-phenoxybenzyl)ether, 2-phenoxybenzyl 2-phenyl-2-trifluoromethylethyl ether or 4-fluoro-3-phenoxybenzyl 2-(4-methoxyphenyl)-2-trifluoromethylpropyl ether.
Claim 7
Dependent Claim
19 words
The method of claim 4 in which said compound is 5-(4-fluoro-3-phenoxyphenyl)-2-(4-methoxyphenyl)-2-trifluoromethylpentane, 4-(3-phenoxyphenyl)-1-phenyl-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-methoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-isopropoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(6-phenoxy-2-pyridyl)-1-trifluoromethylbutane, 4-(3-phenoxyphenyl)-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane, or [4-(4-fluoro-3-phenoxy)phenyl]-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane.
Claim 8
Dependent Claim
29 words
A method of combatting insects and acarids which comprises applying to the insects or acarids or to their locus an effective amount of a compound claimed in claim 2.
Claim 9
Dependent Claim
21 words
Insecticidal and acaricidal composition according to claim 3 in which said compound is [2-(4-ethoxyphenyl)-2-trifluoromethylpropyl](4-fluoro-3-phenoxybenzyl)ether, 2-phenoxybenzyl 2-phenyl-2-trifluoromethylethyl ether or 4-fluoro-3-phenoxybenzyl 2-(4-methoxyphenyl)-2-trifluoromethylpropyl ether.
Claim 10
Dependent Claim
22 words
Insecticidal and acaricidal composition according to claim 3 in which said compound is 5-(4-fluoro-3-phenoxyphenyl)-2-(4-methoxyphenyl)-2-trifluoromethylpentane, 4-(3-phenoxyphenyl)-1-phenyl-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-methoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-isopropoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(6-phenoxy-2-pyridyl)-1-trifluoromethylbutane, 4-(3-phenoxyphenyl)-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane, or [4-(4-fluoro-3-phenoxy)phenyl]-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane.
Claim 11
Dependent Claim
19 words
Insecticidal and acaricidal composition which comprises a compound claimed in claim 2 in admixture with an agriculturally acceptable diluent.
Claim 12
Dependent Claim
18 words
Alkane or alkoxyalkane derivative according to claim 1 which is [2-(4-ethoxyphenyl)-2-trifluoromethylpropyl](4-fluoro-3-phenoxybenzyl)ether, 2-phenoxybenzyl 2-phenyl-2-trifluoromethylethyl ether or 4-fluoro-3-phenoxybenzyl 2-(4-methoxyphenyl)-2-trifluoromethylpropyl ether.
Claim 13
Dependent Claim
19 words
Alkane or alkoxyalkane derivative according to claim 1 which is 5-(4-fluoro-3-phenoxyphenyl)-2-(4-methoxyphenyl)-2-trifluoromethylpentane, 4-(3-phenoxyphenyl)-1-phenyl-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-methoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-isopropoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(6-phenoxy-2-pyridyl)-1-trifluoromethylbutane, 4-(3-phenoxyphenyl)-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane, and [4-(4-fluoro-3-phenoxy)phenyl]-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-12-13 | 1992-06-13 | 1992-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-12-13 | 1996-06-13 | 1996-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-12-13 | 2000-06-13 | 2000-12-13 | $7700.00 | Window Closed / Lapsed |