US4199595A
Expired / Lapsed
US
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M-phenoxybenzyl and α-cyano-M-phenoxybenzyl esters of 2-haloalkyl (oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids
Assignee: Wyeth Holdings LLC
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Filing: 1978-03-20
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Granted: 1980-04-22
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Expires: 1998-03-20
Abstract
Abstract The invention is m-phenoxybenzyl esters of 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful insecticidal and acaricidal agents.
Inventors
- 👤 Gerald Berkelhammer
- 👤 Venkataraman Kameswaran
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 10:06
CPC Classifications
C; C07; C07C; C07C255/00; A; A01; A01N; A01N37/00; A01N37/36; A01N37/38; A01N37/44; A01N37/48; A01N41/00; A01N41/02; A01N41/10; A01N47/00; A01N47/02; C07C317/00; C07C323/00; C07C327/00; C07C329/00; C07C41/00; C07C41/01; C07C41/05; C07C41/06; C07C41/18; C07C41/30; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/70; C07C47/00; C07C47/52; C07C47/575; C07C51/00; C07C51/08; C07C51/347; C07C51/363; C07C51/367; C07C51/58; C07C51/60
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
101 words
A compound having the formula: ##STR152## wherein RCF 2 X--, Y and Z, are all meta or para to the carbon to which the alkanoic acid ester group is attached, and X is O, S, SO or SO 2 ; Y and Z are each H, Cl, F, Br, NO 2 , CH 3 or OCH 3 ; R is H, F, CHF 2 or CF 3 ; R 2 is ethyl, n-propyl, isopropyl, isopropenyl or t-butyl; R 3 is H, CN or --C.tbd.CH, and R 4 is H, F, Cl, CH 3 or OCH 3 or the optical isomers thereof.
Claim 2
Dependent Claim
101 words
A compound having the formula: ##STR152## wherein RCF 2 X--, Y and Z, are all meta or para to the carbon to which the alkanoic acid ester group is attached, and X is O, S, SO or SO 2 ; Y and Z are each H, Cl, F, Br, NO 2 , CH 3 or OCH 3 ; R is H, F, CHF 2 or CF 3 ; R 2 is ethyl, n-propyl, isopropyl, isopropenyl or t-butyl; R 3 is H, CN or --C.tbd.CH, and R 4 is H, F, Cl, CH 3 or OCH 3 or the optical isomers thereof.
Claim 3
Dependent Claim
67 words
A compound according to claim 1 of the formula: ##STR153## wherein RCF 2 X-- is meta or para to the carbon to which the alkanoic acid ester group is attached; R is H or F; X is O or S; R 2 is ethyl, n-propyl or isopropyl; R 3 is H, CN or --C.tbd.CH and R 4 is H, F, Cl, CH 3 or OCH 3 .
Claim 4
Dependent Claim
30 words
A compound according to claim 2 wherein R is H or F; R 2 is isopropyl; R 3 is CN, X is O and R 4 is H or F.
Claim 5
Dependent Claim
8 words
A compound according to claim 2; α-cyano-m-phenoxybenzyl α-isopropyl-4-difluoromethoxyphenylacetate.
Claim 6
Dependent Claim
8 words
A compound according to claim 2; (±)-α-cyano-m-phenoxybenzyl (+)-α-isopropyl-4-difluoromethyoxyphenylacetate.
Claim 7
Dependent Claim
8 words
A compound according to claim 2; α-cyano-m-phenoxybenzyl α-isopropyl-4-trifluoromethoxyphenylacetate.
Claim 8
Dependent Claim
8 words
A compound according to claim 2; (±)-α-cyano-m-phenoxybenzyl (+)-α-isopropyl-4-trifluoromethoxyphenylacetate.
Claim 9
Dependent Claim
8 words
A compound according to claim 2; α-cyano-m-phenoxybenzyl α-ethyl-4-trifluoromethoxyphenylacetate.
Claim 10
Dependent Claim
8 words
A compound according to claim 2; m-phenoxybenzyl α-ethyl-4-trifluoromethoxyphenylacetate.
Claim 11
Dependent Claim
8 words
A compound according to claim 2; α-cyano-m-phenoxybenzyl α-ethyl-4-difluoromethoxyphenylacetate.
Claim 12
Dependent Claim
8 words
A compound according to claim 2; m-phenoxybenzyl α-isopropyl-4-trifluoromethoxyphenylacetate.
Claim 13
Dependent Claim
8 words
A compound according to claim 2; m-phenoxybenzyl α-isopropyl-4-difluoromethoxyphenylacetate.
Claim 14
Dependent Claim
8 words
A compound according to claim 2; α-cyano-m-phenoxybenzyl α-isopropyl-4-trifluoromethylthiophenylacetate.
Claim 15
Dependent Claim
8 words
A compound according to claim 2; α-cyano-m-(p-fluorophenoxy)benzyl α-isopropyl-4-difluoromethoxyphenylacetate.
Claim 16
Dependent Claim
8 words
A compound according to claim 2; α-cyano-m-(p-fluorophenoxy)benzyl α-isopropyl-4-trifluoromethoxyphenylacetate.
Claim 17
Dependent Claim
8 words
A compound according to claim 1; α-cyano-m-phenoxybenzyl α-isopropyl-3-chloro-4-difluoromethoxyphenylacetate.
Claim 18
Independent Claim
128 words
A method for controlling insects and acarina comprising contacting the insects and acarina, their habitat, breeding grounds or feed, with an insecticidally or acaricidally effective amount of a compound of the formula: ##STR154## wherein RCF 2 X--, Y and Z, are all meta or para to the carbon to which the alkanoic acid ester group is attached, and X is O, S, SO or SO 2 ; Y and Z are each H, Cl, F, Br, NO 2 , CH 3 or OCH 3 ; R is H, F, CHF 2 or CF 3 ; R 2 is ethyl, n-propyl, isopropyl, isopropenyl or t-butyl; R 3 is H, CN or --C.tbd.CH, and R 4 is H, F, Cl, CH 3 or OCH 3 or the optical isomers thereof.
Claim 19
Independent Claim
128 words
A method for controlling insects and acarina comprising contacting the insects and acarina, their habitat, breeding grounds or feed, with an insecticidally or acaricidally effective amount of a compound of the formula: ##STR154## wherein RCF 2 X--, Y and Z, are all meta or para to the carbon to which the alkanoic acid ester group is attached, and X is O, S, SO or SO 2 ; Y and Z are each H, Cl, F, Br, NO 2 , CH 3 or OCH 3 ; R is H, F, CHF 2 or CF 3 ; R 2 is ethyl, n-propyl, isopropyl, isopropenyl or t-butyl; R 3 is H, CN or --C.tbd.CH, and R 4 is H, F, Cl, CH 3 or OCH 3 or the optical isomers thereof.
Claim 20
Dependent Claim
71 words
A method according to claim 17 wherein the compound is of the formula: ##STR155## wherein RCF 2 X is meta or para to the carbon to which the alkanoic acid ester group is attached; R is H or F; X is O or S; R 2 is ethyl, n-propyl or isopropyl; R 3 is H, CN or --C.tbd.CH and R 4 is H, F, Cl, CH 3 or OCH 3 .
Claim 21
Dependent Claim
12 words
A method according to claim 18 wherein the compound is α-cyano-m-phenoxybenzyl α-isopropyl-4-difluoromethoxyphenylacetate.
Claim 22
Dependent Claim
12 words
A method according to claim 18 wherein the compound is (±)-α-cyano-m-phenoxybenzyl (+)-α-isopropyl-4-difluoromethoxyphenylacetate.
Claim 23
Dependent Claim
12 words
A method according to claim 18 wherein the compound is (±)-α-cyano-m-phenoxybenzyl (+)-α-isopropyl-4-trifluoromethoxyphenylacetate.
Claim 24
Dependent Claim
12 words
A method according to claim 18 wherein the compound is m-phenoxybenzyl α-ethyl-4-trifluoromethoxyphenoxyacetate.
Claim 25
Dependent Claim
12 words
A method according to claim 18 wherein the compound is m-phenoxybenzyl α-isopropyl-4-trifluoromethoxyphenylacetate.
Claim 26
Independent Claim
135 words
A method for the systemic control of insects and acarina that feed on the body fluids of livestock and domestic animals comprising orally or parenterally administering to the animal host a systemically effective amount of a compound having the formula: ##STR156## wherein RCF 2 X--, Y and Z, are all meta or para to the carbon to which the alkanoic acid ester group is attached, and X is O, S, SO or SO 2 ; Y and Z are each H, Cl, F, Br, NO 2 , CH 3 OCH 3 ; R is H, F, CHF 2 or CF 3 ; R 2 is ethyl, n-propyl, isopropyl, isopropenyl or t-butyl; R 3 is H, CN or --C.tbd.CH, and R 4 is H, F, Cl, CH 3 or OCH 3 or the optical isomers thereof.
Claim 27
Independent Claim
135 words
A method for the systemic control of insects and acarina that feed on the body fluids of livestock and domestic animals comprising orally or parenterally administering to the animal host a systemically effective amount of a compound having the formula: ##STR156## wherein RCF 2 X--, Y and Z, are all meta or para to the carbon to which the alkanoic acid ester group is attached, and X is O, S, SO or SO 2 ; Y and Z are each H, Cl, F, Br, NO 2 , CH 3 OCH 3 ; R is H, F, CHF 2 or CF 3 ; R 2 is ethyl, n-propyl, isopropyl, isopropenyl or t-butyl; R 3 is H, CN or --C.tbd.CH, and R 4 is H, F, Cl, CH 3 or OCH 3 or the optical isomers thereof.
Claim 28
Dependent Claim
12 words
A method according to claim 24 wherein X is S or O.
Claim 29
Dependent Claim
16 words
A method according to claim 25 wherein the compound is orally administered to the host animal.
Claim 30
Dependent Claim
16 words
A method according to claim 25 wherein the compound is parenterally administed to the host animal.
Claim 31
Dependent Claim
113 words
An insecticidal composition comprising a compound of the formula: ##STR157## wherein RCF 2 X--, Y and Z, are all meta or para to the carbon to which the alkanoic acid ester group is attached, and X is O, S, SO or SO 2 ; Y and Z are each H, Cl, F, Br, NO 2 , CH 3 or OCH 3 ; R is H, F, CHF 2 or CF 3 ; R 2 is ethyl, n-propyl, isopropyl, isopropenyl or t-butyl; R 3 is H, CN or --C.tbd.CH, and R 4 is H, F, Cl, CH 3 or OCH 3 or the optical isomers thereof; an emulsifying agent, a surfactant and a solvent.
Claim 32
Dependent Claim
113 words
An insecticidal composition comprising a compound of the formula: ##STR157## wherein RCF 2 X--, Y and Z, are all meta or para to the carbon to which the alkanoic acid ester group is attached, and X is O, S, SO or SO 2 ; Y and Z are each H, Cl, F, Br, NO 2 , CH 3 or OCH 3 ; R is H, F, CHF 2 or CF 3 ; R 2 is ethyl, n-propyl, isopropyl, isopropenyl or t-butyl; R 3 is H, CN or --C.tbd.CH, and R 4 is H, F, Cl, CH 3 or OCH 3 or the optical isomers thereof; an emulsifying agent, a surfactant and a solvent.
Claim 33
Dependent Claim
15 words
A composition according to claim 28 wherein X of the formula is S or O.
References Cited (Backward Citations)
US4058622A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-04-22 | 1983-10-22 | 1984-04-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-04-22 | 1987-10-22 | 1988-04-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-04-22 | 1991-10-22 | 1992-04-22 | $7700.00 | Window Closed / Lapsed |