Patent US3940419A successfully refreshed from Google Patents.
US3940419A
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Phthalimide derivatives and their use as plant growth regulants
Assignee: Wyeth Holdings LLC
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Filing: 1973-07-25
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Granted: 1976-02-24
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Expires: 1993-07-25
Abstract
Abstract The invention is a novel class of phthalimido derivatives represented by a formula: ##SPC1## Or ##SPC2## Wherein W is hydrogen or alkyl C 1 -C 4 ; X and X' each represent hydrogen, halogen, alkyl C 1 -C 4 , CF 3 , alkoxy(C 1 -C 4 ), benzyloxy, di(C 1 -C 4 )alkylamino, C 1 -C 4 alkylthio, hydroxy, C 1 -C 4 alkylsulfonyl, alkanoylamino C 1 -C 4 or nitro; Y is --COOR 3 , --CONHR 8 , --CONR 3 R 4 , --CONHN(R 5 ) 2 , --CONHN + (R 6 ) 3 . halide - , --CN or --COR 7 with the proviso that at least one of X and X' is a substituent other than hydrogen; R 1 and R 2 each represent alkyl C 1 -C 4 or when taken together with the carbon to which they are attached form cycloalkyl C 4 -C 11 optionally substituted with methyl; R 3 and R 4 each represent hydrogen or alkyl C 1 -C 4 ; R 5 and R 6 each represent alkyl C 1 -C 2 ; R 7 is halogen and R 8 is --CH 3 or ##SPC3## Where Z and Z' are hydrogen, alkyl C 1 -C 2 , halogen, --CF 3 or --OCH 3 , is a single or double bond with the proviso that there be only 0 or 1 double bond in the ring and a method for regulating the growth of plants with these compounds and with compounds having the above structure wherein X and X' each represent hydrogen.
Inventors
- 👤 Robert Eugene Diehl
- 👤 Bryant Leonidas Walworth
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 06:57
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07C; C07C65/00; C07C65/21; C07C65/24
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
221 words
A compound having the formula: ##SPC53## or ##SPC54## wherein W is hydrogen or alkyl C 1 -C 4 ; X and X' each represents hydrogen, halogen, alkyl C 1 -C 4 , CF 3 , alkoxy C 1 -C 4 , benzyloxy, di(C 1 -C 4 )alkylamino, C 1 -C 4 alkylthio, hydroxy, C 1 -C 4 alkylsulfonyl, alkanoylamino C 1 -C 4 or nitro; Y is --CONHR 8 ---CONR 3 R 4 , --CONHN(R 5 ) 2 , --CONHN + (R 6 ) 3 .halide - --CN or --COR 7 with the proviso that at least one of X and X' is a substituent other than hydrogen; R 1 and R 2 each represent alkyl C 1 -C 4 or when taken together with the carbon to which they are attached form cycloalkyl C 4 -C 11 optionally substituted with methyl; R 3 and R 4 each represent hydrogen or alkyl C 1 -C 4 ; R 5 and R 6 each represent alkyl C 1 -C 2 , R 7 is halogen, R 8 is --CH 3 or ##SPC55## where Z and Z' are hydrogen, alkyl C 1 -C 2 , halogen, --CF 3 or --OCH 3 and is a single or double bond with the proviso that there be only 0 or 1 double bond in the ring.
Claim 2
Dependent Claim
221 words
A compound having the formula: ##SPC53## or ##SPC54## wherein W is hydrogen or alkyl C 1 -C 4 ; X and X' each represents hydrogen, halogen, alkyl C 1 -C 4 , CF 3 , alkoxy C 1 -C 4 , benzyloxy, di(C 1 -C 4 )alkylamino, C 1 -C 4 alkylthio, hydroxy, C 1 -C 4 alkylsulfonyl, alkanoylamino C 1 -C 4 or nitro; Y is --CONHR 8 ---CONR 3 R 4 , --CONHN(R 5 ) 2 , --CONHN + (R 6 ) 3 .halide - --CN or --COR 7 with the proviso that at least one of X and X' is a substituent other than hydrogen; R 1 and R 2 each represent alkyl C 1 -C 4 or when taken together with the carbon to which they are attached form cycloalkyl C 4 -C 11 optionally substituted with methyl; R 3 and R 4 each represent hydrogen or alkyl C 1 -C 4 ; R 5 and R 6 each represent alkyl C 1 -C 2 , R 7 is halogen, R 8 is --CH 3 or ##SPC55## where Z and Z' are hydrogen, alkyl C 1 -C 2 , halogen, --CF 3 or --OCH 3 and is a single or double bond with the proviso that there be only 0 or 1 double bond in the ring.
Claim 3
Dependent Claim
14 words
A compound according to claim 1 wherein Y is --CONR 3 R 4 .
Claim 4
Dependent Claim
14 words
A compound according to claim 1 wherein Y is --CONHN(R 5 ) 2 .
Claim 5
Dependent Claim
18 words
A comppound according to claim 1 wherein Y is --CONHN + (R 6 ) 3 .halide - .
Claim 6
Dependent Claim
10 words
A compound according to claim 1 wherein Y is --CN.
Claim 7
Dependent Claim
12 words
A compound according to claim 1 wherein Y is --COR 7 .
Claim 8
Dependent Claim
12 words
A compound according to claim 1, wherein Y is --CONHR 8 .
Claim 9
Dependent Claim
7 words
A compound according to claim 2, 1-(3-chlorophthalimido)cyclohexanecarboxamide.
Claim 10
Dependent Claim
7 words
A compound according to claim 2, 1-(3-chlorophthalimido)cyclopentanecarboxamide.
Claim 11
Dependent Claim
7 words
A compound according to claim 2, 1-(4-chlorophthalimido)cyclohexanecarboxamide.
Claim 12
Dependent Claim
7 words
A compound according to claim 2, 1-(4-methylphthalimido)-1-cyclohexanecarboxamide.
Claim 13
Dependent Claim
7 words
A compound according to claim 2, 1-(3,4,5,6-tetrahydrophthalimido)-1-cylohexanecarboxamide.
Claim 14
Dependent Claim
7 words
A compound according to claim 2, α-isobutyl-α-methyl-α-(3-chlorophthalamido)acetamide.
Claim 15
Dependent Claim
7 words
A compound according to claim 2, 1-(3-trifluoromethylphthalimido)cyclohexanecarboxamide.
Claim 16
Dependent Claim
7 words
A compound according to claim 2, 1-(3,5-dichlorophthalamido)-1-cyclohexanecarboxamide.
Claim 17
Dependent Claim
240 words
A process for the preparation of compounds having the formula: ##SPC56## or ##SPC57## wherein W is hydrogen or alkyl C 1 -C 4 ; X and X ' each represent hydrogen, halogen, alkyl C 1 -C 4 , CF 3 , alkoxy C 1 -C 4 , benzyloxy, di(C 1 -C 4 )alkylamino, C 1 -C 4 alkylthio, hydroxy, C 1 -C 4 alkylsulfonyl, alkanoylamino C 1 -C 4 , or nitro; Y is --CN or CONH 2 ; R 1 and R 2 each represent alkyl C 1 -C 4 or when taken together with the carbon to which they are attached form cycloalkyl C 4 -C 11 optionally substituted with methyl; and is a single or double bond, with the proviso that there be only 0 or 1 double bond in the ring; comprising reacting a compound having the formula: ##SPC58## or ##SPC59## where X, X', W and are as described above, with a compound having the structure: ##EQU6## where R 1 and R 2 are as described above, in the presence of an inert solvent at a temperature between 20°C. and 60°C. to give the phthalamic acid; treating the thus-formed phthalamic acid with a dehydrating agent of acetic anhydride, acetylchloride or thionyl chloride at a temperature of from 0°C. to 100°C. to yield the phthalimidonitrile and treating the thus-formed phthalimidonitrile with a strong acid at a temperature between about -10°C. and 30°C. to form the phthalimido acetamide.
Claim 18
Dependent Claim
240 words
A process for the preparation of compounds having the formula: ##SPC56## or ##SPC57## wherein W is hydrogen or alkyl C 1 -C 4 ; X and X ' each represent hydrogen, halogen, alkyl C 1 -C 4 , CF 3 , alkoxy C 1 -C 4 , benzyloxy, di(C 1 -C 4 )alkylamino, C 1 -C 4 alkylthio, hydroxy, C 1 -C 4 alkylsulfonyl, alkanoylamino C 1 -C 4 , or nitro; Y is --CN or CONH 2 ; R 1 and R 2 each represent alkyl C 1 -C 4 or when taken together with the carbon to which they are attached form cycloalkyl C 4 -C 11 optionally substituted with methyl; and is a single or double bond, with the proviso that there be only 0 or 1 double bond in the ring; comprising reacting a compound having the formula: ##SPC58## or ##SPC59## where X, X', W and are as described above, with a compound having the structure: ##EQU6## where R 1 and R 2 are as described above, in the presence of an inert solvent at a temperature between 20°C. and 60°C. to give the phthalamic acid; treating the thus-formed phthalamic acid with a dehydrating agent of acetic anhydride, acetylchloride or thionyl chloride at a temperature of from 0°C. to 100°C. to yield the phthalimidonitrile and treating the thus-formed phthalimidonitrile with a strong acid at a temperature between about -10°C. and 30°C. to form the phthalimido acetamide.
References Cited (Backward Citations)
US3712907A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-02-23 | 1979-08-25 | 1980-02-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-02-23 | 1983-08-25 | 1984-02-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-02-23 | 1987-08-25 | 1988-02-24 | $7700.00 | Window Closed / Lapsed |