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US4240823A
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New plant growth regulating compositions which contain derivatives of N-acyl methionine
Assignee: Bayer CropScience SA
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Filing: 1977-03-01
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Granted: 1980-12-23
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Expires: 1997-03-01
Abstract
Abstract Compounds of the formula: ##STR1## in which R 1 is hydrogen, optionally halogenated alkyl, optionally halogenated cycloalkyl, optionally halogenated alkenyl, optionally halogenated aralkenyl or aryloxyalkenyl mono or bicyclic aryl (optionally substituted by halogen, alkyl, trifluoromethyl, nitro, cyano, amino, hydroxyl, alkoxy, aminosulphonyl or alkylcarbonyloxy), or monocyclic or bicyclic heterocyclic of 5-11 chain members and having one or two hetero-atoms (optionally substituted), and R 2 is a carboxylic acid group or a salt or ester thereof, is found to have plant growth regulating activity.
Inventors
- 👤 Claude Clapot
- 👤 Jean Vial
- 👤 Jacqueline Mourier
- 👤 Jean C. Boch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 10:32
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/81; C07D213/82; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
334 words
A plant growth-regulating composition comprising an agricultural carrier; and, as the active material, a plant growth-regulating effective amount, in the range of from about 0.001 g/l to about 10 g/l, or when in wettable powder form from about 20 to about 95% by weight of active material, or when in concentrate suspension form from about 10 to about 75% of active material, or when in emulsifiable concentrate form from about 10 to about 50% weight/volume of active material, of at least one compound of the formula: ##STR64## in which: R 1 represents a hydrogen atom, a (C 2 to C 20 ) alkyl radical, a halogenated (C 1 to C 20 ) alkyl radical, an optionally halogenated (C 3 to C 6 ) cycloalkyl radical, an optionally halogenated (C 2 to C 20 ) alkenyl radical, an optionally halogenated phenylalkenyl or phenyloxyalkenyl radical (with a C 2 to C 4 alkenyl part), a phenyl or naphthyl radical optionally substituted by one or more identical or different atoms or radicals from amongst halogen atoms, (C 1 to C 4 ) alkyl radicals, trifluoromethyl, nitro, cyano, m-trifluoromethyl-benzoyl and o-, m-, or p-fluorobenzoyl substituted amino, hydroxyl, alkoxy (with a C 1 to C 4 alkyl part), aminosulphonyl or alkoxycarbonyl (with a C 1 to C 4 alkyl part), or a heterocyclic radical selected from the group consisting of furyl and pyridyl, and R 2 represents a carboxylic acid group or a salt which this group can form with an inorganic base or with a primary, secondary or tertiary amine, a ##STR65## group, in which R 3 is a (C 1 to C 4 ) alkyl radical optionally substituted by one or more hydroxyl groups, a --CN group or a ##STR66## group in which R 4 and R 5 , which may be identical or different, represent a hydrogen atom or a (C 1 to C 4 ) alkyl radical with the proviso that when said composition is in solution form, it further comprises a surface active agent.
Claim 2
Dependent Claim
334 words
A plant growth-regulating composition comprising an agricultural carrier; and, as the active material, a plant growth-regulating effective amount, in the range of from about 0.001 g/l to about 10 g/l, or when in wettable powder form from about 20 to about 95% by weight of active material, or when in concentrate suspension form from about 10 to about 75% of active material, or when in emulsifiable concentrate form from about 10 to about 50% weight/volume of active material, of at least one compound of the formula: ##STR64## in which: R 1 represents a hydrogen atom, a (C 2 to C 20 ) alkyl radical, a halogenated (C 1 to C 20 ) alkyl radical, an optionally halogenated (C 3 to C 6 ) cycloalkyl radical, an optionally halogenated (C 2 to C 20 ) alkenyl radical, an optionally halogenated phenylalkenyl or phenyloxyalkenyl radical (with a C 2 to C 4 alkenyl part), a phenyl or naphthyl radical optionally substituted by one or more identical or different atoms or radicals from amongst halogen atoms, (C 1 to C 4 ) alkyl radicals, trifluoromethyl, nitro, cyano, m-trifluoromethyl-benzoyl and o-, m-, or p-fluorobenzoyl substituted amino, hydroxyl, alkoxy (with a C 1 to C 4 alkyl part), aminosulphonyl or alkoxycarbonyl (with a C 1 to C 4 alkyl part), or a heterocyclic radical selected from the group consisting of furyl and pyridyl, and R 2 represents a carboxylic acid group or a salt which this group can form with an inorganic base or with a primary, secondary or tertiary amine, a ##STR65## group, in which R 3 is a (C 1 to C 4 ) alkyl radical optionally substituted by one or more hydroxyl groups, a --CN group or a ##STR66## group in which R 4 and R 5 , which may be identical or different, represent a hydrogen atom or a (C 1 to C 4 ) alkyl radical with the proviso that when said composition is in solution form, it further comprises a surface active agent.
Claim 3
Dependent Claim
153 words
A composition according to claim 1, wherein said active material is at least one compound of the formula: ##STR67## in which: R n represents from one to three identical or different atoms or radicals chosen from amongst halogen atoms and (C 1 to C 4 ) alkyl, trifluoromethyl, nitro, m-trifluoromethyl-benzoyl and o-, m-, or p-fluorobenzoyl acrylated amino, hydroxyl, alkoxy (with a C 1 to C 4 alkyl part) or alkylcarbonyloxy (with a C 1 to C 4 alkyl part) radicals and R 6 represents a carboxylic acid group or a salt which this group can form with an inorganic base with a primary, secondary or tertiary amine ##STR68## group in which R 7 is a C 1 to C 4 alkyl radical, a ##STR69## group in which R 8 and R 9 , which may be identical or different, are a hydrogen atom or a methyl or ethyl radical, or a --CN group.
Claim 4
Dependent Claim
41 words
A composition according to claim 2, wherein said active material is at least one compound of the formula: ##STR70## in which R 6 has the same meaning as in claim 2 and X represents a chlorine atom or a hydrogen atom.
Claim 5
Dependent Claim
45 words
A composition according to claim 2, wherein R 6 is a carboxylic acid group or a salt obtained by the action of the said acid on an inorganic base, or a --CO--O--R 7 group wherein R 7 is a C 1 to C 4 alkyl.
Claim 6
Dependent Claim
62 words
A composition according to claim 1, wherein said compound is a derivative of 4-methylthio-butyric acid in which the R 1 -CO-NH is a member of the group consisting of (D,L)-2-(3',5'-dichloro-benzamido); (D,L)-2(4'-chloro-cinnamido); (D,L)-2-benzamido; (D,L)-2-(2'-chloro-benzamido); (D,L)-2-(2'-fluoro-benzamido); (D,L)-2-(3'-chloro-benzamido); (D,L)-2-(3'-bromo-benzamido); (D,L)-2-(4'-fluoro-benzamido); (D,L)-2-(2',4'-dichloro-benzamido); (D,L)-2-(2',5'-dichloro-benzamido); (D,L)-2-(3'-chloro-4'-fluoro-benzamido); (D,L)-2-(2'-methyl-benzamido); (D,L)-2-(3'-methyl-benzamido); (D,L)-2-(4'-t-butyl-benzamido); (D,L)-2-(2'-methoxy-benzamido); (D,L)-2-(3'-trifluoromethyl-benzamido); (D,L)-2-(2'-nitro-benzamido); (D,L)-2-(3'-nitro-benzamido); (D,L)-2-(3'-chloro-4'-isopropyl-benzamido); (D,L)-2-(2',5'-dihydroxy-benzamido); (D,L)-2-(2'-hydroxy-5'-methoxy-benzamido); (D,L)-2-(2',5'-di-acetoxy-benzamido); (D,L)-2-(2',3'-di-acetoxy-benzamido); (D,L)-2-(2'-hydroxy-3'-methyl-benzamido); (D,L)-2-(2'-hydroxy-5'-bromo-benzamido); (D,L)-2-(-2'-methoxy-5'-aminosulfonyl-benzamido); (D,L)-2-(naphthamido-1'); (D,L)-2-[-2'hydroxy-5'-(m-trifluoromethyl-benzamido)benzamido]; (D,L)-2-[-2'-hydroxy-5'-(m-fluoro-benzamido)benzamido]; (D,L)-2-[-2'-hydroxy-5'-(p-fluoro-benzamido)benzamido]; (D,L)-2-[-2'-hydroxy-4'-(o-fluoro-benzamido)benzamido]; and (D,L)-2-(cinnamido).
Claim 7
Dependent Claim
13 words
A composition according to claim 1, wherein the active compound is (D,L)-2-(3',5'-dichlorobenzamido)-4-methylthiobutyric acid.
Claim 8
Dependent Claim
13 words
A composition according to claim 1, wherein the active compound is (D,L)-2-(3'-chloro-benzamido)-4-methylthio-butyric acid.
Claim 9
Dependent Claim
12 words
A composition according to claim 1, wherein the active compound is (D,L)-ethyl-2-(3',5'-dichlorobenzamido)-4-methylthiobutyrate.
Claim 10
Dependent Claim
12 words
A composition according to claim 1, wherein the active compound is (D,L)-ethyl-2-(cinnamido)-4-methylthiobutyrate.
Claim 11
Dependent Claim
12 words
A composition according to claim 1, wherein the active compound is (D,L)-ethyl-2-(3'-chloro-benzamido)-4-methylthiobutyrate.
Claim 12
Dependent Claim
24 words
A composition according to claim 1, wherein the active compound has as R 1 the group ##STR71## and as R 2 the --CN group.
Claim 13
Dependent Claim
41 words
A composition according to claim 1, wherein said compound is an ester of 4-methyl thiobutyric acid in which the R 1 --CO--NH is a member of the group consisting of (D,L)-ethyl-2-(3',5'-dichlorobenzamido); (D,L)-ethyl-2-(cinnamido); (D,L)-ethyl-2-(2'-chlorobenzamido); (D,L)-ethyl-2-(3'-chloro-benzamido); (D,L)-ethyl-2-(3'-chloro-4'-fluoro-benzamido); (D,L)-methyl-2-(2'-hydroxy-benzamido); (D,L)-ethyl-2-(-3'-nitro-benzamido); (D,L)-ethyl-2-(-2'-methoxy-5'-aminosulfonyl); (D,L)-ethyl-2-[2'-hydroxy-5'-(o-fluoro-benzamido)benzamido]; and (D,L)-n-butyl-2-(3',5'-dichlorobenzamido).
Claim 14
Dependent Claim
246 words
A process for modifying the growth of plants comprising applying to said plants a growth-modifying-effective amount of a plant growth-regulating compound of the formula ##STR72## in which: R 1 represents a hydrogen atom, an optionally halogenated (C 1 to C 20 ) alkyl radical, an optionally halogenated (C 3 to C 6 ) cycloalkyl radical, an optionally halogenated (C 2 to C 20 ) alkenyl radical, an optionally halogenated phenylalkenyl or phenyloxyalkenyl radical (with a C 2 to C 4 alkenyl part), a phenyl or naphthyl radical optionally substituted by one or more identical or different atoms or radicals from amongst halogen atoms, (C 1 to C 4 ) alkyl radicals, trifluoromethyl, nitro, cyano, m-trifluoromethylbenzoyl and o-, m-, or p-fluorobenzoyl substituted amino, hydroxyl, alkoxy (with a C 1 to C 4 alkyl part), aminosulphonyl or alkoxycarbonyl (with a C 1 to C 4 alkyl part), or a heterocyclic radical selected from the group consisting of furyl and pyridyl, and R 2 represents a carboxylic acid group or a salt which this group can form with an inorganic base or with a primary, secondary or tertiary amine, a ##STR73## group, in which R 3 is a (C 1 to C 4 ) alkyl radical optionally substituted by one or more hydroxyl groups, a --CN group or a ##STR74## group in which R 4 and R 5 , which may be identical or different, represent a hydrogen atom or a (C 1 to C 4 ) alkyl radical.
Claim 15
Dependent Claim
246 words
A process for modifying the growth of plants comprising applying to said plants a growth-modifying-effective amount of a plant growth-regulating compound of the formula ##STR72## in which: R 1 represents a hydrogen atom, an optionally halogenated (C 1 to C 20 ) alkyl radical, an optionally halogenated (C 3 to C 6 ) cycloalkyl radical, an optionally halogenated (C 2 to C 20 ) alkenyl radical, an optionally halogenated phenylalkenyl or phenyloxyalkenyl radical (with a C 2 to C 4 alkenyl part), a phenyl or naphthyl radical optionally substituted by one or more identical or different atoms or radicals from amongst halogen atoms, (C 1 to C 4 ) alkyl radicals, trifluoromethyl, nitro, cyano, m-trifluoromethylbenzoyl and o-, m-, or p-fluorobenzoyl substituted amino, hydroxyl, alkoxy (with a C 1 to C 4 alkyl part), aminosulphonyl or alkoxycarbonyl (with a C 1 to C 4 alkyl part), or a heterocyclic radical selected from the group consisting of furyl and pyridyl, and R 2 represents a carboxylic acid group or a salt which this group can form with an inorganic base or with a primary, secondary or tertiary amine, a ##STR73## group, in which R 3 is a (C 1 to C 4 ) alkyl radical optionally substituted by one or more hydroxyl groups, a --CN group or a ##STR74## group in which R 4 and R 5 , which may be identical or different, represent a hydrogen atom or a (C 1 to C 4 ) alkyl radical.
Claim 16
Dependent Claim
155 words
A process for regulating the growth of plants according to claim 13, wherein said compound is of the formula: ##STR75## in which: R n represents from one to three identical or different atoms or radicals chosen from amongst halogen atoms and (C 1 to C 4 ) alkyl, trifluoromethyl, nitro, m-trifluoromethyl-benzoyl and o-, m-, or p-fluorobenzyl acrylated amino, hydroxyl, alkoxy (with a C 1 to C 4 alkyl part) or alkylcarbonyloxy (with a C 1 to C 4 alkyl part) radicals and R 6 represents a carboxylic acid group or a salt which this group can form with an inorganic base with a primary, secondary or tertiary amine a ##STR76## group in which R 7 is a C 1 to C 4 alkyl radical, a ##STR77## group in which R 8 and R 9 , which may be identical or different, are a hydrogen atom or a methyl or ethyl radical, or a --CN group.
Claim 17
Dependent Claim
42 words
A process for regulating the growth of plants according to claim 13, wherein said compound is of the formula: ##STR78## in which R 6 has the same meaning as in claim 29 and X represents a chlorine atom or a hydrogen atom.
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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) | 1983-12-23 | 1984-06-23 | 1984-12-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-23 | 1988-06-23 | 1988-12-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-23 | 1992-06-23 | 1992-12-23 | $7700.00 | Window Closed / Lapsed |