US4340765A
Expired / Lapsed
US
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4-Phenoxy-2-butene derivatives as plant growth regulators
Assignee: Avantor Performance Materials LLC
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Filing: 1980-08-14
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Granted: 1982-07-20
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Expires: 2000-08-14
Abstract
Abstract 4-Phenoxy-2-butene derivatives are disclosed as inhibitors of cytokinin plant growth regulatory activity and as possessing seed germination regulatory properties and senescence delaying activity when applied to plants. 4-Phenoxy-2-butene derivatives can also be useful as plant dwarfing agents, agents to retard seedling development or as herbicides.
Inventors
- 👤 Gary M. Gray
- 👤 George Schwartzkopf, Jr.
- 👤 J. T. Baker Chemical Co.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 15:57
CPC Classifications
C; C07; C07C; C07C323/00; A; A01; A01N; A01N39/00; A01N39/02; C07C41/00; C07C41/48; C07C41/50; C07C41/56; C07C45/00; C07C45/51; C07C45/511; C07C45/515; C07C45/56; C07C45/57; C07C45/58; C07C47/00; C07C47/20; C07C47/277; C07C49/00; C07C49/20; C07C49/255; C07C57/00; C07C57/52; C07C57/58; C07C57/60
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
108 words
A 4-phenoxy-2-butene compound of the formula ##STR6## and phytopharmaceutically acceptable salts thereof, wherein R 1 and R 2 are selected from hydrogen and --CH 3 with the proviso that one of R 1 and R 2 is --CH 3 and the other is hydrogen; R 3 is hydrogen Y is selected from the group consisting of (lower)alkyl, halo, nitro, --CF 3 , --S--(lower)alkyl, --O--(lower)alkyl, --O--acetyl, hydroxy, --NH--acetyl, amino, --NH(lower)alkyl, --N--di(lower)alkyl, and a fused benzene ring; and n is equal to 0, 1 or 2, wherein the term (lower)alkyl as used in the foregoing definitions includes straight or branched chain alkyl radicals containing from 1 to 6 carbon atoms.
Claim 2
Dependent Claim
108 words
A 4-phenoxy-2-butene compound of the formula ##STR6## and phytopharmaceutically acceptable salts thereof, wherein R 1 and R 2 are selected from hydrogen and --CH 3 with the proviso that one of R 1 and R 2 is --CH 3 and the other is hydrogen; R 3 is hydrogen Y is selected from the group consisting of (lower)alkyl, halo, nitro, --CF 3 , --S--(lower)alkyl, --O--(lower)alkyl, --O--acetyl, hydroxy, --NH--acetyl, amino, --NH(lower)alkyl, --N--di(lower)alkyl, and a fused benzene ring; and n is equal to 0, 1 or 2, wherein the term (lower)alkyl as used in the foregoing definitions includes straight or branched chain alkyl radicals containing from 1 to 6 carbon atoms.
Claim 3
Dependent Claim
46 words
A compound of the formula of claim 1 wherein R 1 is hydrogen and R 2 is --CH 3 ; Y is selected from the group consisting of halo, --O--(lower)alkyl, --O--acetyl, hydroxy, --NH--acetyl and a fused benzene ring; and n is equal to 1 or 2.
Claim 4
Dependent Claim
14 words
A compound of claim 2 wherein Y is halo selected from chlorine or bromine.
Claim 5
Dependent Claim
28 words
A compound of claim 3 wherein Y is chlorine and n is equal to 2 and the Y's are in the 2- and 4-positions on the phenyl ring.
Claim 6
Dependent Claim
8 words
A compound of claim 2 which is (E)-4(3-acetamidophenoxy)-2-methyl-2-buten-1-al.
Claim 7
Dependent Claim
8 words
A compound of claim 2 which is (E)-4(4-acetamidophenoxy)-2-methyl-2-buten-1-al.
Claim 8
Dependent Claim
8 words
A compound of claim 2 which is (E)-4(3-methoxyphenoxy)-2-methyl-2-buten-1-al.
Claim 9
Dependent Claim
8 words
A compound of claim 4 which is (E)-4(2,4-dichlorophenoxy)-2-methyl-2-buten-1-al.
Claim 10
Dependent Claim
8 words
A compound of claim 2 which is (E)-4(3-hydroxyphenoxy)-2-methyl-2-buten-1-al.
Claim 11
Dependent Claim
8 words
A compound of claim 2 which is (E)-4(3-acetoxyphenoxy)-2-methyl-2-buten-1-al.
Claim 12
Dependent Claim
8 words
A compound of claim 2 which is (E)-4(1-naphthyloxy)-2-methyl-2-buten-1-al.
Claim 13
Independent Claim
131 words
A method of regulating the growth of leguminous plants which comprises applying to the plant locus a plant growth regulating effective amount of a 4-phenoxy-2-butene compound of the formula ##STR7## and phytopharmaceutically acceptable salts thereof, wherein R 1 and R 2 are selected from hydrogen and --CH 3 with the proviso that one of R 1 and R 2 is --CH 3 and the other is hydrogen; R 3 is hydrogen; Y is selected from the group consisting of (lower)alkyl, halo, nitro, --CF 3 , --S--(lower)alkyl), --O--(lower)alkyl, --O--acetyl, hydroxy, --NH--acetyl, amino, --NH(lower)alkyl, --N--di(lower)alkyl, and a fused benzene ring; and n is equal to 0, 1 or 2, wherein the term (lower)alkyl is used in the foregoing definitions includes straight or branched chain alkyl radicals containing from 1 to 6 carbon atoms.
Claim 14
Independent Claim
131 words
A method of regulating the growth of leguminous plants which comprises applying to the plant locus a plant growth regulating effective amount of a 4-phenoxy-2-butene compound of the formula ##STR7## and phytopharmaceutically acceptable salts thereof, wherein R 1 and R 2 are selected from hydrogen and --CH 3 with the proviso that one of R 1 and R 2 is --CH 3 and the other is hydrogen; R 3 is hydrogen; Y is selected from the group consisting of (lower)alkyl, halo, nitro, --CF 3 , --S--(lower)alkyl), --O--(lower)alkyl, --O--acetyl, hydroxy, --NH--acetyl, amino, --NH(lower)alkyl, --N--di(lower)alkyl, and a fused benzene ring; and n is equal to 0, 1 or 2, wherein the term (lower)alkyl is used in the foregoing definitions includes straight or branched chain alkyl radicals containing from 1 to 6 carbon atoms.
Claim 15
Dependent Claim
43 words
The method of claim 12 wherein R 1 is hydrogen and R 2 is --CH 3 ; Y is selected from the group consisting of halo, --O--(lower)alkyl, --O--acetyl, hydroxy, --NH--acetyl and a fused benzene ring; and n is equal to 1 or 2.
Claim 16
Dependent Claim
14 words
The method of claim 13 wherein Y is halo selected from chlorine and bromine.
Claim 17
Dependent Claim
28 words
The method of claim 14 wherein Y is chlorine and n is equal to 2 and the Y's are in the 2- and 4-positions on the phenyl ring.
Claim 18
Dependent Claim
11 words
The method of claim 15 wherein the 4-phenoxy-2-buten-1-al compound is (E)-4(2,4-dichlorophenoxy)-2-methyl-2-buten-1-al.
Claim 19
Dependent Claim
25 words
The method of claim 12 wherein the compound is applied to the plant locus in an amount of from about 0.05 to about 20 kg/hectare.
Claim 20
Dependent Claim
25 words
The method of claim 13 wherein the compound is applied to the plant locus in an amount of from about 0.05 to about 20 kg/hectare.
Claim 21
Dependent Claim
25 words
The method of claim 14 wherein the compound is applied to the plant locus in an amount of from about 0.05 to about 20 kg/hectare.
Claim 22
Dependent Claim
25 words
The method of claim 15 wherein the compound is applied to the plant locus in an amount of from about 0.05 to about 20 kg/hectare.
Claim 23
Dependent Claim
25 words
The method of claim 16 wherein the compound is applied to the plant locus in an amount of from about 0.05 to about 20 kg/hectare.
Claim 24
Dependent Claim
136 words
A plant growth regulating composition comprising an inert carrier material and from about 5 to about 95 parts by weight of a plant growth regulating compound selected from a 4-phenoxy-2-butene compound of the formula ##STR8## and phytopharmaceutically acceptable salts thereof, wherein R 1 and R 2 are selected from hydrogen and --CH 3 with the proviso that one of R 1 and R 2 is --CH 3 and the other is hydrogen; R 3 is hydrogen; Y is selected from the group consisting of (lower)alkyl, halo, nitro, --CF 3 , --S--(lower)alkyl, --O--(lower)alkyl, --O--acetyl, hydroxy, --NH--acetyl, amino, --NH(lower)alkyl, --N--di(lower)alkyl, and a fused benzene ring; and n is equal to 0, 1 or 2, wherein the term (lower)alkyl as used in the foregoing definitions includes straight or branched chain alkyl radicals containing from 1 to 6 carbon atoms.
Claim 25
Dependent Claim
136 words
A plant growth regulating composition comprising an inert carrier material and from about 5 to about 95 parts by weight of a plant growth regulating compound selected from a 4-phenoxy-2-butene compound of the formula ##STR8## and phytopharmaceutically acceptable salts thereof, wherein R 1 and R 2 are selected from hydrogen and --CH 3 with the proviso that one of R 1 and R 2 is --CH 3 and the other is hydrogen; R 3 is hydrogen; Y is selected from the group consisting of (lower)alkyl, halo, nitro, --CF 3 , --S--(lower)alkyl, --O--(lower)alkyl, --O--acetyl, hydroxy, --NH--acetyl, amino, --NH(lower)alkyl, --N--di(lower)alkyl, and a fused benzene ring; and n is equal to 0, 1 or 2, wherein the term (lower)alkyl as used in the foregoing definitions includes straight or branched chain alkyl radicals containing from 1 to 6 carbon atoms.
Claim 26
Dependent Claim
45 words
The plant growth regulating composition of claim 22 wherein R 1 is hydrogen and R 2 is --CH 3 ; Y is selected from the group consisting of halo, --O--(lower)alkyl, --O--acetyl, hydroxy, --NH--acetyl and a fused benzene ring; n is equal to 1 or 2.
Claim 27
Dependent Claim
17 words
The plant growth regulating composition of claim 23 wherein Y is halo selected from chlorine and bromine.
Claim 28
Dependent Claim
31 words
The plant growth regulating composition of claim 24 wherein Y is chlorine and n is equal to 2 and the Y's are in the 2- and 4-positions on the phenyl ring.
Claim 29
Dependent Claim
14 words
The plant growth regulating composition of claim 25 wherein the 4-phenoxy-2-buten-1-al compound is (E)-4(2,4-dichlorophenoxy)-2-methyl-2-buten-1-al.
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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) | 1985-07-19 | 1986-01-18 | 1986-07-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-07-19 | 1990-01-18 | 1990-07-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-07-19 | 1994-01-18 | 1994-07-20 | $7700.00 | Window Closed / Lapsed |