US4287201A
Expired / Lapsed
US
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Anovulatory method and chicken feed compositions
Assignee: Merck and Co Inc
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Filing: 1980-03-03
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Granted: 1981-09-01
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Expires: 2000-03-03
Abstract
Abstract 2-(Substituted phenylimino)imidazolidines delay the onset of egg production in young pullets and inerrupt egg production in mature hens and are useful in producing an artificial molt.
Inventors
- 👤 George Olson
- 👤 Richard L. Tolman
- 👤 Roger M. Weppelman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 20:05
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/04; C07D233/28; C07D233/44; C07D233/50
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
159 words
An anovulatory composition comprising a solid poultry feedstuff having intimately dispersed therein at least an effective anovulatory amount of a compound of structural formula: ##STR14## or a non-toxic salt thereof, wherein: R is (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) bromo, or (5) iodo; R 1 and R 2 are independently (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) fluoro, (5) bromo, (6) iodo, (7) hydrogen, (8) nitro, (9) amino, (10) C 1-3 alkylamino, (11) di(C 1-3 alkyl)amino, (12) hydroxy, (13) carboxy, (14) C 1-3 alkoxycarbonyl, (15) C 1-4 alkanoyl, (16) C 1-4 alkylthio, (17) trifluoromethylthio, (18) phenylthio, (19) C 1-3 alkylphenylthio (20) C 1-3 alkoxyphenylthio (21) chlorophenylthio, (22) bromophenylthio, (23) phenoxy, (24) C 1-3 alkylphenoxy, (25) C 1-3 alkoxyphenoxy, (26) chlorophenoxy, (27) bromophenoxy, (28) amino-C 1-4 alkyl, (29) C 1-3 alkylamino-C 1-4 alkyl, (30) di(C 1-3 alkyl)amino-C 1-4 alkyl, (31) hydroxy C 1-4 alkyl, or (32) C 1-3 alkoxy-C 1-4 alkyl.
Claim 2
Dependent Claim
159 words
An anovulatory composition comprising a solid poultry feedstuff having intimately dispersed therein at least an effective anovulatory amount of a compound of structural formula: ##STR14## or a non-toxic salt thereof, wherein: R is (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) bromo, or (5) iodo; R 1 and R 2 are independently (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) fluoro, (5) bromo, (6) iodo, (7) hydrogen, (8) nitro, (9) amino, (10) C 1-3 alkylamino, (11) di(C 1-3 alkyl)amino, (12) hydroxy, (13) carboxy, (14) C 1-3 alkoxycarbonyl, (15) C 1-4 alkanoyl, (16) C 1-4 alkylthio, (17) trifluoromethylthio, (18) phenylthio, (19) C 1-3 alkylphenylthio (20) C 1-3 alkoxyphenylthio (21) chlorophenylthio, (22) bromophenylthio, (23) phenoxy, (24) C 1-3 alkylphenoxy, (25) C 1-3 alkoxyphenoxy, (26) chlorophenoxy, (27) bromophenoxy, (28) amino-C 1-4 alkyl, (29) C 1-3 alkylamino-C 1-4 alkyl, (30) di(C 1-3 alkyl)amino-C 1-4 alkyl, (31) hydroxy C 1-4 alkyl, or (32) C 1-3 alkoxy-C 1-4 alkyl.
Claim 3
Dependent Claim
36 words
The anovulatory composition of claim 1 wherein R is C 1-4 alkyl, one of R 1 and R 2 is hydrogen, and the other is C 1-4 alkyl, fluoro, chloro, or C 1-3 alkoxy-C 1-4 alkyl.
Claim 4
Dependent Claim
23 words
The anovulatory composition of claim 2 wherein the anovulatory compound is: 2-(2,6-dimethylphenylimino)imidazolidine, 2-(3-chloro-2-methylphenylimino)imidazolidine, 2-(6-chloro-2-methylphenylimino)imidazolidine, 2-(2-methyl-4-methoxymethylphenylimino) imidazolidine, or 2-(5-fluoro-2-methylphenylimino)imidazolidine or a non-toxic salt thereof.
Claim 5
Dependent Claim
24 words
The composition of claim 1, 2, or 3 wherein the anovulatory compound comprises from about 20 to about 500 parts per million by weight.
Claim 6
Dependent Claim
23 words
The composition of claim 2 or 3 wherein the anovulatory compound comprises from about 30 to about 250 parts per million by weight.
Claim 7
Dependent Claim
176 words
A poultry feed premix composition comprising a solid poultry feedstuff having intimately dispersed therein an anovulatory compound in sufficient amount so that after dilution to final poultry feed said feed contains an effective amount of the anovulatory compound of structural formula: ##STR15## or a non-toxic salt thereof, wherein: R is (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) bromo, or (5) iodo; R 1 and R 2 are independently (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) fluoro, (5) bromo, (6) iodo, (7) hydrogen, (8) nitro, (9) amino, (10) C 1-3 alkylamino, (11) di(C 1-3 alkyl)amino, (12) hydroxy, (13) carboxy, (14) C 1-3 alkoxycarbonyl, (15) C 1-4 alkanoyl, (16) C 1-4 alkylthio, (17) trifluoromethylthio, (18) phenylthio, (19) C 1-3 alkylphenylthio (20) C 1-3 alkoxyphenylthio (21) chlorophenylthio, (22) bromophenylthio, (23) phenoxy, (24) C 1-3 alkylphenoxy, (25) C 1-3 alkoxyphenoxy, (26) chlorophenoxy, (27) bromophenoxy, (28) amino-C 1-4 alkyl, (29) C 1-3 alkylamino-C 1-4 alkyl, (30) di(C 1-3 alkyl)amino-C 1-4 alkyl, (31) hydroxy C 1-4 alkyl, or (32) C 1-3 alkoxy-C 1-4 alkyl.
Claim 8
Dependent Claim
176 words
A poultry feed premix composition comprising a solid poultry feedstuff having intimately dispersed therein an anovulatory compound in sufficient amount so that after dilution to final poultry feed said feed contains an effective amount of the anovulatory compound of structural formula: ##STR15## or a non-toxic salt thereof, wherein: R is (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) bromo, or (5) iodo; R 1 and R 2 are independently (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) fluoro, (5) bromo, (6) iodo, (7) hydrogen, (8) nitro, (9) amino, (10) C 1-3 alkylamino, (11) di(C 1-3 alkyl)amino, (12) hydroxy, (13) carboxy, (14) C 1-3 alkoxycarbonyl, (15) C 1-4 alkanoyl, (16) C 1-4 alkylthio, (17) trifluoromethylthio, (18) phenylthio, (19) C 1-3 alkylphenylthio (20) C 1-3 alkoxyphenylthio (21) chlorophenylthio, (22) bromophenylthio, (23) phenoxy, (24) C 1-3 alkylphenoxy, (25) C 1-3 alkoxyphenoxy, (26) chlorophenoxy, (27) bromophenoxy, (28) amino-C 1-4 alkyl, (29) C 1-3 alkylamino-C 1-4 alkyl, (30) di(C 1-3 alkyl)amino-C 1-4 alkyl, (31) hydroxy C 1-4 alkyl, or (32) C 1-3 alkoxy-C 1-4 alkyl.
Claim 9
Dependent Claim
37 words
The poultry feed premix of claim 6 wherein R is C 1-4 alkyl, one of R 1 and R 2 is hydrogen, and the other is C 1-4 alkyl, fluoro, chloro, or C 1-3 alkoxy-C 1-4 alkyl.
Claim 10
Dependent Claim
24 words
The poultry feed premix of claim 7, wherein the anovulatory compound is: 2-(2,6-dimethylphenylimino)imidazolidine, 2-(3-chloro-2-methylphenylimino)imidazolidine, 2-(6-chloro-2-methylphenylimino)imidazolidine, 2-(2-methyl-4-methoxymethylphenylimino) imidazolidine, or 2-(5-fluoro-2-methylphenylimino)imidazolidine or a non-toxic salt thereof.
Claim 11
Dependent Claim
25 words
The poultry feed premix of claim 6, 7 or 8 wherein the anovulatory agent comprises about 2 to about 50% by weight of the composition.
Claim 12
Dependent Claim
25 words
The poultry feed premix of claim 6, 7 or 8 wherein the anovulatory agent comprises about 5 to about 25% by weight of the composition.
Claim 13
Independent Claim
159 words
A method of arresting ovulation in poultry which comprises the administration to the poultry of an effective amount of an anovulatory compound of formula: ##STR16## or a non-toxic salt thereof, wherein: R is (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) bromo, or (5) iodo; R 1 and R 2 are independently (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) fluoro, (5) bromo, (6) iodo, (7) hydrogen, (8) nitro, (9) amino, (10) C 1-3 alkylamino, (11) di(C 1-3 alkyl)amino, (12) hydroxy, (13) carboxy, (14) C 1-3 alkoxycarbonyl, (15) C 1-4 alkanoyl, (16) C 1-4 alkylthio, (17) trifluoromethylthio, (18) phenylthio, (19) C 1-3 alkylphenylthio, (20) C 1-3 alkoxyphenylthio, (21) chlorophenylthio, (22) bromophenylthio, (23) phenoxy, (24) C 1-3 alkylphenoxy, (25) C 1-3 alkoxyphenoxy, (26) chlorophenoxy, (27) bromophenoxy, (28) amino-C 1-4 alkyl, (29) C 1-3 alkylamino-C 1-4 alkyl, (30) di(C 1-3 alkyl)amino-C 1-4 alkyl, (31) hydroxy C 1-4 alkyl, or (32) C 1-3 alkoxy-C 1-4 alkyl.
Claim 14
Independent Claim
159 words
A method of arresting ovulation in poultry which comprises the administration to the poultry of an effective amount of an anovulatory compound of formula: ##STR16## or a non-toxic salt thereof, wherein: R is (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) bromo, or (5) iodo; R 1 and R 2 are independently (1) C 1-4 alkyl, (2) C 2-5 alkenyl, (3) chloro, (4) fluoro, (5) bromo, (6) iodo, (7) hydrogen, (8) nitro, (9) amino, (10) C 1-3 alkylamino, (11) di(C 1-3 alkyl)amino, (12) hydroxy, (13) carboxy, (14) C 1-3 alkoxycarbonyl, (15) C 1-4 alkanoyl, (16) C 1-4 alkylthio, (17) trifluoromethylthio, (18) phenylthio, (19) C 1-3 alkylphenylthio, (20) C 1-3 alkoxyphenylthio, (21) chlorophenylthio, (22) bromophenylthio, (23) phenoxy, (24) C 1-3 alkylphenoxy, (25) C 1-3 alkoxyphenoxy, (26) chlorophenoxy, (27) bromophenoxy, (28) amino-C 1-4 alkyl, (29) C 1-3 alkylamino-C 1-4 alkyl, (30) di(C 1-3 alkyl)amino-C 1-4 alkyl, (31) hydroxy C 1-4 alkyl, or (32) C 1-3 alkoxy-C 1-4 alkyl.
Claim 15
Dependent Claim
35 words
The method of claim 11 wherein R is C 1-4 alkyl, one of R 1 and R 2 is hydrogen, and the other is C 1-4 alkyl, fluoro, chloro, or C 1-3 alkoxy-C 1-4 alkyl.
Claim 16
Dependent Claim
22 words
The method of claim 12 wherein the anovulatory compound is: 2-(2,6-dimethylphenylimino)imidazolidine, 2-(3-chloro-2-methylphenylimino)imidazolidine, 2-(6-chloro-2-methylphenylimino)imidazolidine, 2-(2-methyl-4-methoxymethylphenylimino) imidazolidine, or 2-(5-fluoro-2-methylphenylimino)imidazolidine or a non-toxic salt thereof.
Claim 17
Dependent Claim
36 words
The method of claim 11, 12 or 13 wherein the compound is administered orally as a component of the poultry feed, comprising from about 20 to about 500 parts per million by weight of the feed.
Claim 18
Dependent Claim
36 words
The method of claim 11, 12 or 13 wherein the compound is administered orally as a component of the poultry feed comprising from about 30 to about 250 parts per million by weight of the feed.
Claim 19
Dependent Claim
38 words
The method of claim 11, 12 or 13 wherein the compound or non-toxic salt thereof is administered orally as a component of drinking water comprising about 25 to about 100 parts per million by weight of the water.
Claim 20
Dependent Claim
38 words
The method of claim 11, 12 or 13 wherein the compound or non-toxic salt thereof is administered orally as a component of drinking water comprising about 25 to about 100 parts per million by weight of the water.
Claim 21
Dependent Claim
12 words
The method of claim 17 wherein the non-toxic salt is the hydrochloride.
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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) | 1984-08-31 | 1985-03-02 | 1985-09-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-31 | 1989-03-02 | 1989-09-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-31 | 1993-03-02 | 1993-09-01 | $7700.00 | Window Closed / Lapsed |