US4576628A
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Oxime ethers, compositions containing them and the use thereof
Assignee: Novartis Corp
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Filing: 1985-05-13
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Granted: 1986-03-18
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Expires: 2005-05-13
Abstract
Abstract The oxime ethers of the formula I below are able to act as antidotes or safeners to protect cultivated plants from the phytotoxic effects of herbicides. Such cultivated plants are preferably sorghum, cereals, maize and rice, and herbicides are principally chloroacetanilides and thiocarbamates. The oxime ethers have the formula I ##STR1## wherein n is 1 or 2, each of R 1 and R 2 is hydrogen or C 1 -C 4 alkyl each of R 3 and R 4 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl or nitro; each of R 5 and R 6 independently of the other is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 8 alkoxyalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, or together form a 2- to 6-membered alkylene or alkenylene bridge which may be substituted by 1 to 4 C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 8 alkoxyalkyl or C 3 -C 8 alkenyloxyalkyl groups; each of A and B independently of the other is oxygen or sulfur, or one of A and b is the methine group, X is a fluorinated C 1 -C 3 alkyl radical which may also additionally contain chlorine, and Y is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or phenyl.
Inventors
- 👤 Henry Martin
- 👤 Urs Fricker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 18:07
CPC Classifications
C; C07; C07D; C07D319/00; C07D319/04; C07D319/06; A; A01; A01N; A01N25/00; A01N25/32; C07D307/00; C07D307/02; C07D307/04; C07D307/10; C07D307/12; C07D309/00; C07D309/02; C07D309/04; C07D309/06; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/18; C07D317/22; C07D321/00; C07D321/02; C07D321/04; C07D321/06; C07D339/00; C07D339/02; C07D339/06; C07D339/08
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
112 words
An oxime ether of the formula ##STR51## wherein n is 1 or 2 each of R 1 and R 2 is hydrogen or C 1 -C 4 -alkyl, each of R 3 and R 4 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or nitro R 5 and R 6 are independently of each other C 1 -C 4 alkyl or C 3 -C 4 alkenyl X is a fluorinated C 1 -C 3 alkyl radical which may also additionally contain chlorine and Y is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
Claim 2
Dependent Claim
112 words
An oxime ether of the formula ##STR51## wherein n is 1 or 2 each of R 1 and R 2 is hydrogen or C 1 -C 4 -alkyl, each of R 3 and R 4 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or nitro R 5 and R 6 are independently of each other C 1 -C 4 alkyl or C 3 -C 4 alkenyl X is a fluorinated C 1 -C 3 alkyl radical which may also additionally contain chlorine and Y is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
Claim 3
Dependent Claim
44 words
An oxime ether of claim 1 wherein n is 1, R 1 and R 2 are hydrogen, R 3 and R 4 are hydrogen or halogen, R 5 and R 6 are C 1 -C 4 alkyl, X is trifluoromethyl and Y is hydrogen.
Claim 4
Dependent Claim
4 words
1-Phenyl-1-(2,2-dimethoxy-ethoximino)-2,2,2-trifluoroethane of claim 1.
Claim 5
Dependent Claim
4 words
1-Phenyl-1-(2,2-diethoxy-ethoximino)-2,2,2-trifluoroethane of claim 1.
Claim 6
Dependent Claim
4 words
1-(4-Chlorophenyl)-1-(2,2-dimethoxy-ethoximino)-2,2,2-trifluoroethane of claim 1.
Claim 7
Dependent Claim
4 words
1-(4-Chlorophenyl)-1-(2,2-diethoxy-ethoximino)-2,2,2-trifluoroethane of claim 1.
Claim 8
Dependent Claim
4 words
1-(4-Fluorophenyl)-1-(2,2-dimethoxy-ethoximino)-2,2,2-trifluoroethane of claim 1.
Claim 9
Dependent Claim
4 words
1-(4-Fluorophenyl)-1-(2,2-diethoxy-ethoximino)-2,2,2-trifluoroethane of claim 1.
Claim 10
Dependent Claim
150 words
A composition for controlling weeds in crops of culture plants which comprises (a) a herbicidally effective amount of a herbicide selected from the group consisting of thiocarbamates, haloacetanilides, phenoxyphenoxypropionates, pyridyloxyphenoxypropionates and dinitroanilines, and (b) as crop safening agent an oxime ether of the formula ##STR52## wherein n is 1 or 2 each of R 1 and R 2 is hydrogen or C 1 -C 4 -alkyl, each of R 3 and R 4 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyoxy or nitro, R 5 and R 6 are independently of each other C 1 -C 4 alkyl or C 3 -C 4 alkenyl X is a fluorinated C 1 -C 3 alkyl radical which may also additionally contain chlorine and Y is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
Claim 11
Dependent Claim
150 words
A composition for controlling weeds in crops of culture plants which comprises (a) a herbicidally effective amount of a herbicide selected from the group consisting of thiocarbamates, haloacetanilides, phenoxyphenoxypropionates, pyridyloxyphenoxypropionates and dinitroanilines, and (b) as crop safening agent an oxime ether of the formula ##STR52## wherein n is 1 or 2 each of R 1 and R 2 is hydrogen or C 1 -C 4 -alkyl, each of R 3 and R 4 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyoxy or nitro, R 5 and R 6 are independently of each other C 1 -C 4 alkyl or C 3 -C 4 alkenyl X is a fluorinated C 1 -C 3 alkyl radical which may also additionally contain chlorine and Y is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
Claim 12
Dependent Claim
83 words
A composition of claim 9 in which the herbicide is a haloacetanilide of the formula ##STR53## wherein each of R 8 and R 9 is hydrogen, halogen, lower alkyl or lower alkoxy, Z is hydrogen or lower alkyl, A is methylene, 1-1-ethylene or 1,2-ethylene, each of which is optionally substituted by 1 or 2 lower alkyl groups, and R 10 is lower alkoxy, allyloxy, lower alkoxycarbonyl, N,N-di(lower alkyl)-carbamoyl, N-propargylcarbamoyl, cyano, ethynyl, 1,3-dioxolan-2-yl, 2-tetrahydrofuranyl, optionally substituted benzoyl, optionally substituted 1,3,4-oxadiazol-2-yl or optionally substituted 1,3,4-triazol-2-yl.
Claim 13
Independent Claim
157 words
A method of protecting rice, sorghum, wheat and maize crops from the phytoxic action of thiocarbamate, triazinone haloacetanilide, phenoxyphenoxypropionate pyridyloxyphenoxypropionate or dinitroaniline herbicides, which comprises adding to the herbicides, applying to the locus of the crops, or applying to the seeds of said crops, as antidote, a compound of the formula ##STR54## wherein n is 1 or 2 each of R 1 and R 2 is hydrogen or C 1 -C 4 -alkyl, each of R 3 and R 4 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or nitro, R 5 and R 6 are independently of each other C 1 -C 4 alkyl or C 3 -C 4 alkenyl X is a fluorinated C 1 -C 3 alkyl radical which may also additionally contain chlorine and Y is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
Claim 14
Independent Claim
157 words
A method of protecting rice, sorghum, wheat and maize crops from the phytoxic action of thiocarbamate, triazinone haloacetanilide, phenoxyphenoxypropionate pyridyloxyphenoxypropionate or dinitroaniline herbicides, which comprises adding to the herbicides, applying to the locus of the crops, or applying to the seeds of said crops, as antidote, a compound of the formula ##STR54## wherein n is 1 or 2 each of R 1 and R 2 is hydrogen or C 1 -C 4 -alkyl, each of R 3 and R 4 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or nitro, R 5 and R 6 are independently of each other C 1 -C 4 alkyl or C 3 -C 4 alkenyl X is a fluorinated C 1 -C 3 alkyl radical which may also additionally contain chlorine and Y is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
Claim 15
Dependent Claim
11 words
A method of claim 11 in which the compound is 1-phenyl-1-(2,2-dimethoxy-ethoximino)-2,2,2-trifluoroethane.
Claim 16
Dependent Claim
11 words
A method of claim 11 in which the compound is 1-(4-chlorophenyl)-1-(2,2-dimethoxyethoximino)-2,2,2-trifluoroethane.
Claim 17
Dependent Claim
11 words
A method of claim 11 in which the compound is 1-(4-chlorophenyl)-1-(2,2-diethoxy-ethoximino)-2,2,2-trifluoroethane.
Claim 18
Dependent Claim
12 words
A method of claim 11 in which the herbicide is 4-amino-6-tert butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one.
Claim 19
Dependent Claim
11 words
A method of claim 11 in which the herbicide is propargyl-[4-(2,4-dichloropyridyl-2-oxy)-phenoxy]-propionate.
References Cited (Backward Citations)
US4497745A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-03-17 | 1989-09-16 | 1990-03-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-03-17 | 1993-09-16 | 1994-03-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-03-17 | 1997-09-16 | 1998-03-18 | $7700.00 | Window Closed / Lapsed |