US4117154A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pesticidally active novel oxime-carbamates of fluorinated ketones
Assignee: Bayer AG
•
Filing: 1977-07-12
•
Granted: 1978-09-26
•
Expires: 1997-07-12
Abstract
Abstract Oxime-carbamates of fluorinated ketones of the formula ##STR1## in which X represents hydrogen or fluorine, R represents alkyl, cycloalkyl, phenyl or phenylalkyl, any of which can optionally be substituted, R 1 and R 2 , which may be identical or different, each represent hydrogen, alkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, alkoxyalkyl, alkylthioalkyl or optionally substituted phenyl, and R 2 can also represent the --SR 3 grouping, R 3 represents alkyl, halogenoalkyl, optionally substituted phenyl or alkoxycarbonyl, or represents a radical identical to that to which the --SR 3 grouping is bonded, or represents the ##STR2## grouping, WHEREIN R 4 represents alkyl and R 5 represents alkyl, dialkylamino or optionally substituted phenyl, And acid addition salts thereof, which possess insecticidal, acaricidal, nematicidal and fungicidal properties.
Inventors
- 👤 Jorg Stetter
- 👤 Ingeborg Hammann
- 👤 Bernhard Homeyer
- 👤 Wolfgang Behrenz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 16:07
CPC Classifications
A; A01; A01N; A01N47/00; A01N47/08; A01N47/10; A01N47/24; C; C07; C07C; C07C45/00; C07C45/61; C07C45/63
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
406 words
An oxime-carbamate of a fluorinated ketone of the formula ##STR33## in which X is hydrogen or fluorine. R is alkyl with 1 to 6 carbon atoms optionally substituted by halogen, nitro, cyano, hydroxyl, --S-C 1-4 -alkyl, --O-C 1-4 -alkyl, --CO-O-C 1-4 alkyl or --O-CO-C 1-4 -alkyl; or phenyl optionally substituted by halogen, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 or 2 carbon atoms and up to 5 halogen atoms; phenylalkyl with 1 to 4 carbon atoms in the alkyl moiety and optionally substituted in the phenyl moiety by halogen, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 to 2 carbon atoms and up to 5 halogen atoms; or cycloalkyl with 5 to 7 carbon atoms optionally substituted by halogen, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 or 2 carbon atoms and up to 5 halogen atoms; R 1 is hydrogen, alkyl with 1 to 12 carbon atoms, alkenyl or alkynyl each with 2 to 4 carbon atoms, halogenoalkyl with up to 2 carbon atoms and up to 5 halogen atoms, halogenoalkenyl with up to 3 carbon atoms and up to 5 halogen atoms, alkoxyalkyl or alkythioalkyl with up to 2 carbon atoms in each alkyl moiety, or phenyl optionally substituted by halogen, alkyl with 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy or halogenoalkylthio each with 1 to 2 carbon atoms and up to 5 halogen atoms, C 1-2 -alkoxy, C 1-2 -alkylthio phenyl, phenoxy, halophenyl, halophenoxy, nitro or cyano; R 2 is any of R 1 or --SR 3 , R 3 is alkyl with 1 to 4 carbon atoms, halogenoalkyl with 1 to 2 carbon atoms and up to 5 halogen atoms, phenyl optionally substituted by halogen, alkyl with 1 or 2 carbon atoms or halogenoalkyl with 1 to 2 carbon atoms and up to 5 halogen atoms; alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy moiety; a radical identical to that to which the --SR 3 is bonded; or --NR 4 -SO 2 -R 5 ; R 4 is alkyl with 1 to 4 carbon atoms; R 5 is alkyl with 1 to 5 carbon atoms; dialkylamino with 1 to 4 carbon atoms in each alkyl moiety; or phenyl optionally substituted by halogen, alkyl with 1 to 2 carbon atoms, halogenoalkyl with 1 to 2 carbon atoms and up to 5 halogen atoms, cyano or nitro, or an acid addition salt.
Claim 2
Dependent Claim
406 words
An oxime-carbamate of a fluorinated ketone of the formula ##STR33## in which X is hydrogen or fluorine. R is alkyl with 1 to 6 carbon atoms optionally substituted by halogen, nitro, cyano, hydroxyl, --S-C 1-4 -alkyl, --O-C 1-4 -alkyl, --CO-O-C 1-4 alkyl or --O-CO-C 1-4 -alkyl; or phenyl optionally substituted by halogen, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 or 2 carbon atoms and up to 5 halogen atoms; phenylalkyl with 1 to 4 carbon atoms in the alkyl moiety and optionally substituted in the phenyl moiety by halogen, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 to 2 carbon atoms and up to 5 halogen atoms; or cycloalkyl with 5 to 7 carbon atoms optionally substituted by halogen, alkyl with 1 to 4 carbon atoms or halogenoalkyl with 1 or 2 carbon atoms and up to 5 halogen atoms; R 1 is hydrogen, alkyl with 1 to 12 carbon atoms, alkenyl or alkynyl each with 2 to 4 carbon atoms, halogenoalkyl with up to 2 carbon atoms and up to 5 halogen atoms, halogenoalkenyl with up to 3 carbon atoms and up to 5 halogen atoms, alkoxyalkyl or alkythioalkyl with up to 2 carbon atoms in each alkyl moiety, or phenyl optionally substituted by halogen, alkyl with 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy or halogenoalkylthio each with 1 to 2 carbon atoms and up to 5 halogen atoms, C 1-2 -alkoxy, C 1-2 -alkylthio phenyl, phenoxy, halophenyl, halophenoxy, nitro or cyano; R 2 is any of R 1 or --SR 3 , R 3 is alkyl with 1 to 4 carbon atoms, halogenoalkyl with 1 to 2 carbon atoms and up to 5 halogen atoms, phenyl optionally substituted by halogen, alkyl with 1 or 2 carbon atoms or halogenoalkyl with 1 to 2 carbon atoms and up to 5 halogen atoms; alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy moiety; a radical identical to that to which the --SR 3 is bonded; or --NR 4 -SO 2 -R 5 ; R 4 is alkyl with 1 to 4 carbon atoms; R 5 is alkyl with 1 to 5 carbon atoms; dialkylamino with 1 to 4 carbon atoms in each alkyl moiety; or phenyl optionally substituted by halogen, alkyl with 1 to 2 carbon atoms, halogenoalkyl with 1 to 2 carbon atoms and up to 5 halogen atoms, cyano or nitro, or an acid addition salt.
Claim 3
Dependent Claim
21 words
The compound according to claim 1, wherein such compound is 1,1-difluoro-3,3-dimethyl-2-methylcarbamoyl-oximino-butane of the formula ##STR34## or an acid addition salt thereof.
Claim 4
Dependent Claim
21 words
The compound according to claim 1, wherein such compound is 1,1-difluoro-3,3-dimethyl-2-[N-methyl-N-(3-trifluoromethylphenylmercapto)]-carbamoyl-oximino-butane of the formula ##STR35## or an acid addition salt thereof.
Claim 5
Dependent Claim
21 words
The compound according to claim 1, wherein such compound is 1,1-difluoro-3,3-dimethyl-2-(N-methyl-N-trichloromethylmercapto)-carbamoyl-oximino-butane of the formula ##STR36## or an acid addition salt thereof.
Claim 6
Dependent Claim
21 words
The compound according to claim 1, wherein such compound is 1-fluoro-3-methyl-2-methylcarbamoyl-oximino-butane of the formula ##STR37## or an acid addition salt thereof.
Claim 7
Dependent Claim
21 words
The compound according to claim 1, wherein such compound is 1-fluoro-3,3-dimethyl-2-(N-methyl-N-dichlorofluoromethylmercapto)carbamoyl-oximino-butane of the formula ##STR38## or an acid addition salt thereof.
Claim 8
Dependent Claim
27 words
An arthropodicidal or nematicidal composition containing as active ingredient an arthropodicidally or nematicidally effective amount of a compound according to claim 1 in admixture with a diluent.
Claim 9
Dependent Claim
33 words
A method of combating arthropods or nematodes which comprises applying to the arthropods or nematodes or to a habitat thereof, an arthropodicidally or nematicidally effective amount of a compound according to claim 1.
Claim 10
Dependent Claim
22 words
The method according to claim 8 wherein such compound is 1,1-difluoro-3,3-dimethyl-2-methylcarbamoyl-oximino-butane, 1,1-difluoro-3,3-dimethyl-2-[N-methyl-N-(3-trifluoromethylphenylmercapto)]-carbamoyl-oximino-butane, 1,1-difluoro-3,3-dimethyl-2-(N-methyl-N-trichloromethylmercapto)-carbamoyl-oximino-butane, 1-fluoro-3-methyl-2-methylcarbamoyl-oximino-butane, or 1-fluoro-3,3-dimethyl-2-(N-methyl-N-dichlorofluoromethylmercapto)-carbamoyl-oximino-butane or an acid addition salt thereof.
References Cited (Backward Citations)
US4029688A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-09-25 | 1982-03-27 | 1982-09-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-09-25 | 1986-03-27 | 1986-09-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-09-25 | 1990-03-27 | 1990-09-26 | $7700.00 | Window Closed / Lapsed |