US4566901A
Expired / Lapsed
US
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Novel oxime ethers, the preparation thereof, compositions containing them and the use thereof
Assignee: Novartis Corp
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Filing: 1983-04-29
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Granted: 1986-01-28
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Expires: 2003-04-29
Abstract
Abstract The invention relates to novel oxime ethers of the formula I ##STR1## wherein R 1 is hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkylthio, lower haloalkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower haloalkylsulfinyl, lower haloalkylsulfonyl or nitro, each of R 2 and R 3 is hydrogen, halogen, lower alkyl, lower alkoxy or lower haloalkoxy, and Q is an unsubstituted or substituted lower alkyl, lower alkenyl, lower alkynyl or cycloalkyl group, a lower alkanoyl radical, an aliphatic, cycloaliphatic, aromatic or heterocyclic acyl radical which may be substituted or unsubstituted, a carbonyl or thiocarbonyl radical, an aryl or aralkyl radical, an acylimidomethyl radical, a phthalimidomethyl radical or a heterocyclic radical. These compounds are able to act as antidotes or safeners for protecting cultivated plants from the phytotoxic action of aggressive herbicides. Preferred crops are sorghum, cereals, maize and rice, and herbicides are chiefly chloroacetanilides and thiocarbamates.
Inventors
- 👤 Henry Martin
- 👤 Urs Fricker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 02:37
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/34; C07D207/36; C07D207/40; C07D207/404; A; A01; A01N; A01N25/00; A01N25/32; C07D207/44; C07D207/444; C07D207/448; C07D207/452; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/63; C07D213/78; C07D213/79; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/30; C07D261/00; C07D261/02; C07D261/06; C07D261/10; C07D261/18; C07D277/00; C07D277/02; C07D277/20; C07D277/32; C07D277/56; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/06; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088; C07D303/00; C07D303/02; C07D303/12; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68; C07D309/00; C07D309/16; C07D309/28; C07D327/00; C07D327/02; C07D327/06; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/38
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
108 words
An oxime ether of the formula I ##STR20## R 1 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 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl or nitro, R 2 and R 3 are each hydrogen, halogen C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkyl, Q is --CH 2 CONH 2 or --CH(CH 3 )CONH 2 ; and X is a fluorinated C 1 -C 3 alkyl radical, which may also contain chlorine.
Claim 2
Dependent Claim
108 words
An oxime ether of the formula I ##STR20## R 1 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 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl or nitro, R 2 and R 3 are each hydrogen, halogen C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkyl, Q is --CH 2 CONH 2 or --CH(CH 3 )CONH 2 ; and X is a fluorinated C 1 -C 3 alkyl radical, which may also contain chlorine.
Claim 3
Dependent Claim
25 words
An oxime ether according to claim 1 of the formula Ia ##STR21## wherein R 1 , Q and X are as defined in claim 1.
Claim 4
Dependent Claim
26 words
An oxime ether according to claim 1 of the formula Ib ##STR22## wherein R 1 , R 2 and Q are as defined in claim 1.
Claim 5
Dependent Claim
24 words
An oxime ether according to claim 1 of the formula Ii ##STR23## wherein R 1 and R 2 are as defined in claim 1.
Claim 6
Dependent Claim
24 words
An oxime ether according to claim 1 of the formula Ij ##STR24## wherein R 1 and R 2 are as defined in claim 1.
Claim 7
Dependent Claim
30 words
An oxime ether according to claim 1, wherein R 1 is hydrogen, halogen, methyl, methoxy, trifluoromethyl or nitro, R 2 is hydrogen, halogen or methyl, and R 3 is hydrogen.
Claim 8
Dependent Claim
9 words
1-Phenyl-1-carbamoylmethoximino-2,2,2-trifluoroethane according to claim 1 of the formula ##STR25##
Claim 9
Dependent Claim
9 words
1-(4-Fluorophenyl)-1-carbamoylmethoximino-2,2,2-trifluoroethane according to claim 1 of the formula ##STR26##
Claim 10
Dependent Claim
9 words
1-(4-Chlorophenyl)-1-carbamoylmethoximino-2,2,2-trifluoroethane according to claim 1 of the formula ##STR27##
Claim 11
Dependent Claim
9 words
1-Phenyl-1-carbamoylmethoximino-2,2,3,3,3-pentafluoropropane according to claim 1 of the formula ##STR29##
Claim 12
Dependent Claim
9 words
1-Phenyl-1-carbamoyleth-1'-oximino-2,2,2-trifluoroethane according to claim 1 of the formula ##STR30##
Claim 13
Dependent Claim
9 words
1-(4-Chlorophenyl)-1-carbamoyleth-1'-oximino-2,2,2-trifluoroethane according to claim 1 of the formula ##STR31##
Claim 14
Dependent Claim
9 words
1-(3-Trifluoromethylphenyl)-1-carbamoyleth-1'-oximino-2,2,2-trifluoroethane according to claim 1 of the formula ##STR32##
Claim 15
Dependent Claim
35 words
A composition for protecting cultivated plants from damage caused by a herbicidal haloacetanilide, thiocarbamate, 1,2,4-triazinone or dinitroaniline, which composition contains an effective amount of an oxime ether of claim 1, together with an inert carrier.
Claim 16
Dependent Claim
36 words
A composition according to claim 15, which contains (a) an effective amount of a herbicidal haloacetanilide or a herbicidal thiocarbamate, and (b) an effective amount of the oxime ether as antidote, together with a suitable carrier.
Claim 17
Dependent Claim
104 words
A composition which contains as active components, effective amounts of (a) a haloacetanilide herbicide of the formula ##STR33## wherein Hal is chlorine or bromine, each of R 4 and R 5 independently of the other is hydrogen, halogen, lower alkyl, alkoxy, alkylthio, haloalkyl, alkoxyalkyl or alkylthioalkyl, Z is hydrogen or methyl, A is methylene, 1,1-ethylene or 1,2-ethylene which may be substituted by 1 or 2 lower alkyl groups, and R 6 is lower alkoxy, hydroxycarbonyl, alkoxycarbonyl, carbamoyl, N-alkylcarbamoyl, N,N-dialkylcarbamoyl, cyano, 1H-pyrazol-1-yl, 1H-1,2,4-triazol-1-yl, alkanoyl, 1,3,4-oxadiazol-2-yl, 5-methyl-1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-3-yl, or 1,3,4-triazol-1-yl, and (b) an oxime ether of claim 1 as antidote, together with a suitable carrier.
Claim 18
Dependent Claim
86 words
A composition according to claim 15 which contains (a) a thiocarbamate of the formula VIII or IX ##STR34## wherein R 7 is lower alkyl, alkenyl, chloroallyl, dichloroallyl, trichloroallyl, benzyl or 4-chlorobenzyl, R 8 is C 2 -C 4 alkyl and R 9 is C 2 -C 4 alkyl or cyclohexyl, and R 8 and R 9 together with the nitrogen atom to which they are attached can form a hexahydro-1H-azepine, decahydroquinoline or 2-methyldecahydroquinoline ring, and (b) an oxime ether as antidote, together with a suitable carrier.
Claim 19
Dependent Claim
62 words
A method of protecting cultivated plants from damage that may be caused by the application of a herbicidal haloacetanilide, thiocarbamate, 1,2,4-triazinone or dinitroaniline, which method comprises (a) treating the locus of the plant before or during application of the herbicide, or (b) treating the seeds or seedlings of the plant itself with an effective amount of an oxime ether 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) | 1989-01-27 | 1989-07-29 | 1990-01-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-01-27 | 1993-07-29 | 1994-01-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-01-27 | 1997-07-29 | 1998-01-28 | $7700.00 | Window Closed / Lapsed |