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US4233056A
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Novel glycylmethylphosphinic acid derivatives, process for their production and use thereof
Assignee: Novartis Corp
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Filing: 1978-08-07
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Granted: 1980-11-11
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Expires: 1998-08-07
Abstract
Abstract The present invention relates to novel herbicidally active and plant growth-regulating glycylmethylphosphinic acid derivatives of the formula ##STR1## wherein R represents hydrogen, --CH 2 COOH or an easily removable radical (e.g. benzyl, tert-butyl), R' represents a --OH or --OR 1 group, in which R 1 is a cation, a lower aliphatic radical, cycloalkyl or NH 2 , R" represents hydrogen, a cation or lower alkyl and R'" represents optionally substituted alkyl or phenyl. These compounds are obtained by reacting a N-substituted glycine HOOC--CH 2 --NH--R with formaldehyde and a phosphonous acid ##STR2## in a strongly acid solution and optionally removing the radical R by catalytic hydrogenation or with HBr. The compounds of the formula I are used as active ingredients of compositions especially for the post-emergent control of weeds or for inhibiting plant growth.
Inventors
- 👤 Ludwig Maier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 01:43
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/30; C07F9/301; A; A01; A01N; A01N57/00; A01N57/18; C07F9/32; C07F9/3205; C07F9/3211
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
140 words
A glycylmethylphosphinic acid derivative of the formula I ##STR33## wherein R represents hydrogen, a C 1 -C 6 alkyl radical, benzyl, diphenylmethyl or triphenylmethyl, or the group HOOC--CH 2 --, R' represents a --OH or --OR 1 group, in which R 1 represents a cation, a C 1 -C 6 alkyl radical, a C 1 -C 6 alkyl radical substituted by halogen, hydroxyl, lower alkoxy, carboxyl or cyano, a lower alkenyl or alkynyl radical, a cycloalkyl radical, or R' represents the amino group, R" represents hydrogen, a cation, and lower alkyl or hydroxyalkyl, R'" represents a C 1 -C 4 alkyl radical which can be mono- or polysubstituted by halogen atoms, hydroxyl or carboxyl groups, or represents a phenyl radical, or a phenyl radical substituted by halogen, lower alkyl, haloalkyl or di-(lower) alkylamino, and the plant physiologically acceptable salts thereof.
Claim 2
Dependent Claim
140 words
A glycylmethylphosphinic acid derivative of the formula I ##STR33## wherein R represents hydrogen, a C 1 -C 6 alkyl radical, benzyl, diphenylmethyl or triphenylmethyl, or the group HOOC--CH 2 --, R' represents a --OH or --OR 1 group, in which R 1 represents a cation, a C 1 -C 6 alkyl radical, a C 1 -C 6 alkyl radical substituted by halogen, hydroxyl, lower alkoxy, carboxyl or cyano, a lower alkenyl or alkynyl radical, a cycloalkyl radical, or R' represents the amino group, R" represents hydrogen, a cation, and lower alkyl or hydroxyalkyl, R'" represents a C 1 -C 4 alkyl radical which can be mono- or polysubstituted by halogen atoms, hydroxyl or carboxyl groups, or represents a phenyl radical, or a phenyl radical substituted by halogen, lower alkyl, haloalkyl or di-(lower) alkylamino, and the plant physiologically acceptable salts thereof.
Claim 3
Dependent Claim
20 words
A glycylmethylphosphinic acid derivative according to claim 1, wherein R in the formula I represents hydrogen or the benzyl group.
Claim 4
Dependent Claim
25 words
A glycylmethylphosphinic acid derivative according to claim 1, wherein R in the formula I represents hydrogen and R'" represents the methyl, trichloromethyl or hydroxymethyl group.
Claim 5
Dependent Claim
40 words
A herbicidal and plant growth-regulating composition consisting essentially of as active ingredient an effective amount of a glycylmethylphosphinic acid derivative of the formula I of claim 1, or a plant physiologically acceptable salt thereof, together with a suitable carrier therefor.
Claim 6
Dependent Claim
28 words
A method of selectively controlling weeds in postemergent application which comprises applying thereto an effective weed controlling amount of a compound of the formula I of claim 1.
Claim 7
Dependent Claim
35 words
A method of controlling the growth of mono- and dicotyledonous plants which comprises applying thereto or the locus thereof an effective plant growth controlling amount of a compound of the formula I of claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-11-11 | 1984-05-12 | 1984-11-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-11 | 1988-05-12 | 1988-11-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-11 | 1992-05-12 | 1992-11-11 | $7700.00 | Window Closed / Lapsed |