US3989840A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Control of animal parasites with ring-substituted N-(2,2-difluoroalkanoyl)-O-phenylenediamines
Assignee: Eli Lilly and Co
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Filing: 1975-07-18
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Granted: 1976-11-02
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Expires: 1995-07-18
Abstract
Abstract A class of substituted o-phenylenediamines are useful parasiticides for the systemic control of insects and acarina which feed on tissues of animals. The compounds, which control both bloodsucking parasites and flesh-eating parasites, are characterized by a single nitro substituent on the benzene ring, and a single fluoroalkyl or chlorodifluoroalkyl substituent on the benzene ring.
Inventors
- 👤 George Oliver Plunkett O'Doherty
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 23:31
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/16; A61K31/165; A61K31/21; A61K31/27
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
213 words
A method of killing insect and acarina parasites which consume living tissues of a host animal which comprises orally or percutaneously administering to the host animal a parasiticidally-effective amount of a compound of the formula: ##SPC10## wherein R° is a 2,2-difluoroalkanoyl radical of the formula ##EQU1## in which Y is hydrogen, chlorine, fluorine, difluoromethyl, perfluoroalkyl of C 1 -C 6 , or a radical of the formula ##EQU2## in which each Z independently is hydrogen or halogen and n is 0 or 1; R 1 is R°, hydrogen, a radical of the formula ##EQU3## in which Y 1 is C 1 -C 4 alkyl or phenyl, C 1 -C 8 alkanoyl, benzoyl, furoyl, naphthoyl, or substituted benzoyl of the formula ##SPC11## in which each Z' independently is halo or nitro, Z" is C 1 -C 4 alkyl or C 1 -C 4 alkoxy, p is 0, 1, or 2, q is 0 or 1, and the sum of p and q is 1-3; R 2 is trifluoromethyl, difluoromethyl, or chlorodifluoromethyl, and the nitro group and R 2 are meta to one another; and subject to the further limitation that where R 1 is hydrogen, the ring position ortho to the --NH--R 1 group bears one of the designated nitro or R 2 moieties.
Claim 2
Independent Claim
213 words
A method of killing insect and acarina parasites which consume living tissues of a host animal which comprises orally or percutaneously administering to the host animal a parasiticidally-effective amount of a compound of the formula: ##SPC10## wherein R° is a 2,2-difluoroalkanoyl radical of the formula ##EQU1## in which Y is hydrogen, chlorine, fluorine, difluoromethyl, perfluoroalkyl of C 1 -C 6 , or a radical of the formula ##EQU2## in which each Z independently is hydrogen or halogen and n is 0 or 1; R 1 is R°, hydrogen, a radical of the formula ##EQU3## in which Y 1 is C 1 -C 4 alkyl or phenyl, C 1 -C 8 alkanoyl, benzoyl, furoyl, naphthoyl, or substituted benzoyl of the formula ##SPC11## in which each Z' independently is halo or nitro, Z" is C 1 -C 4 alkyl or C 1 -C 4 alkoxy, p is 0, 1, or 2, q is 0 or 1, and the sum of p and q is 1-3; R 2 is trifluoromethyl, difluoromethyl, or chlorodifluoromethyl, and the nitro group and R 2 are meta to one another; and subject to the further limitation that where R 1 is hydrogen, the ring position ortho to the --NH--R 1 group bears one of the designated nitro or R 2 moieties.
Claim 3
Dependent Claim
22 words
The method of claim 1 in which the compound is of the formula ##SPC12## wherein R° is defined as in claim 1.
Claim 4
Dependent Claim
13 words
The method of claim 1 in which the compound is N 1 -trifluoroacetyl-3'-nitro-5'-trifluoromethyl-o-phenylenediamine.
Claim 5
Dependent Claim
13 words
The method of claim 1 in which the compound is N 1 -(2,2,3,3-tetrafluoropropionyl)-3'-nitro-5'-trifluoromethyl-o-phenylenediamine.
Claim 6
Dependent Claim
13 words
The method of claim 1 in which the compound is N 1 -trifluoroacetyl-3'-trifluoromethyl-5'-nitro-o-phenylenediamine.
Claim 7
Dependent Claim
13 words
The method of claim 1 in which the compound is N 1 -chlorodifluoroacetyl-3'-nitro-5'-trifluoromethyl-o-phenylenediamine.
Claim 8
Dependent Claim
15 words
The method of claim 1 in which the compound is N 1 -trifluoroacetyl-N 2 -benzoyl-6'-nitro-4'-trifluoromethyl-o-phenylenediamine.
Claim 9
Dependent Claim
15 words
The method of claim 1 in which the compound is N 1 -trifluoroacetyl-N 2 -naphthoyl-6'-nitro-4'-trifluoromethyl-o-phenylenediamine.
Claim 10
Dependent Claim
15 words
The method of claim 1 in which the compound is N 1 -trifluoroacetyl-N 2 -(p-n-butoxybenzoyl)-4'-trifluoromethyl-6'-nitro-o-phenylenediamine.
Claim 11
Dependent Claim
15 words
The method of claim 1 in which the compound is N 1 -trifluoroacetyl-N 2 -(p-nitrobenzoyl)-4'-trifluoromethyl-6'-nitro-o-phenylenediamine.
Claim 12
Dependent Claim
13 words
The method of claim 1 in which the compound is N 1 -heptafluorobutyryl-3'-nitro-5'-trifluoromethyl-o-phenylenediamine.
Claim 13
Dependent Claim
13 words
The method of claim 1 in which the compound is N 1 -pentafluoropropionyl-3'-nitro-5'-trifluoromethyl-o-phenylenediamine.
Claim 14
Dependent Claim
15 words
The method of claim 1 in which the compound is N 1 -trifluoroacetyl-N 2 -methoxycarbonyl-4'-trifluoromethyl-6'-nitro-o-phenylenediamine.
Claim 15
Dependent Claim
13 words
The method of claim 1 in which the compound is N 1 -pentadecafluorooctanoyl-3'-nitro-5'-trifluoromethyl-o-phenylenediamine.
Claim 16
Dependent Claim
15 words
The method of claim 1 in which the compound is N 1 -(2,2,3,3-tetrafluoropropionyl)-N 2 -methoxycarbonyl-6'-nitro-4'-trifluoromethyl-o-phenylenediamine.
Claim 17
Dependent Claim
11 words
The method of claim 1 in which the compound is N-(pentafluoropropionyl)-3'-nitro-5'-trifluoromethyl-o-phenylenediamine.
Claim 18
Dependent Claim
24 words
The method of claim 1 in which from about 1 mg./kg. to about 100 mg./kg. of the compound is administered to the host animal.
Claim 19
Dependent Claim
24 words
The method of claim 17 in which from about 2.5 mg./kg. to about 50 mg./kg. of the compound is administered to the host animal.
Claim 20
Dependent Claim
11 words
The method of claim 17 in which the administration is percutaneous.
Claim 21
Dependent Claim
14 words
The method of claim 19 in which the compound is administered in an implant.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-11-02 | 1980-05-03 | 1980-11-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-11-02 | 1984-05-03 | 1984-11-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-11-02 | 1988-05-03 | 1988-11-02 | $7700.00 | Window Closed / Lapsed |