US4481365A
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Trifluoromethyl-phenoxy-phenyl-silicon derivatives, processes for their preparation, and their use as herbicides and plant-growth regulators
Assignee: Bayer AG
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Filing: 1982-10-12
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Granted: 1984-11-06
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Expires: 2002-10-12
Abstract
Abstract A trifluoromethyl-phenoxy-phenyl-silicon compound is disclosed of the general formula <IMAGE> in which X1 and X2 independently of each other represent a hydrogen, fluorine, chlorine, bromine or iodine atom, Y represents a hydrogen or halogen atom or a cyano or nitro group, n is 0 or 1, m is 0, 1, 2 or 3, p is 0, 1, 2 or 3, X3 and X4 independently of each other represent oxygen or a -CO-O- group, R1, R2, R3 and R4 independently of one another represent a hydrogen atom or a C1 to C5 alkyl group, R5 and R6 independently of each other represent a C1 to C5 alkyl group, and R7 represents a C1 to C5 alkyl or hydroxyl group, a chlorine, bromine, or iodine atom or a C2 to C5 alkenoxy, C2 to C5 alkinoxy, C1 to C5 alkylthio, C2 to C5 alkenyl-thio or C2 to C5 alkinyl-thio group or a C1 to C5 alkoxy group which is straight-chain or branched and optionally substituted by fluorine, chlorine, bromine, iodine, C1 to C5 alkoxy and/or C1 to C5 alkylthio, or represents a radical of the general formula <IMAGE> wherein R8 and R9 independently of each other represent a phenyl radical which is optionally substituted by fluorine, bromine, and/or iodine, or represent a straight-chain or branched C1 to C5 alkyl, C2 to C5 alkenyl or C2 to C5 alkinyl group, or wherein R8 and R9, together with the nitrogen atom to which they are bonded, represent a pyrrolidyl radical which is optionally substituted by methyl and/or ethyl, represent a morpholinyl radical which is optionally substituted by methyl, or represent an azacycloheptyl, piperidyl, 3-methyl-piperidyl, 4-methyl-piperidyl, 2-ethyl-piperidyl, 4-ethyl-piperidyl, 2,3-dimethyl-piperidyl, 2,4-dimethyl-piperidyl, 2,5-dimethyl-piperidyl, or 3,5-dimethyl-piperidyl radical. The trifluoromethyl-phenoxy-phenyl-silicon compounds are useful as herbicides and plant growth regulators. Disclosed are compositions containing the same and methods for their preparation.
Inventors
- 👤 Heinz Forster
- 👤 Ludwig Eue
- 👤 Robert Schmidt
- 👤 Klaus Lurssen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 14:20
CPC Classifications
A; A01; A01N; A01N55/00; C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/10; C07F7/12; C07F7/18; C07F7/1804
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
323 words
A trifluoromethyl-phenoxy-phenyl-silicon compound of the general formula ##STR68## in which X 1 and X 2 independently of each other represent a hydrogen, fluorine, chlorine, bromine or iodine atom, Y represents a hydrogen or halogen atom or a cyano or nitro group, n is 0 or 1, m is 0, 1, 2 or 3, p is 0, 1, 2 or 3, X 3 and X 4 independently of each other represent oxygen or a --CO--O-- group, R 1 , R 2 , R 3 and R 4 independently of one another represent a hydrogen atom or a C 1 to C 5 alkyl group, R 5 and R 6 independently of each other represent a C 1 to C 5 alkyl group, and R 7 represents a C 1 to C 5 alkyl or hydroxyl group, a chlorine, bromine, or iodine atom or a C 2 to C 5 alkenoxy, C 2 to C 5 alkinoxy, C 1 to C 5 alkylthio, C 2 to C 5 alkenyl-thio or C 2 to C 5 alkinyl-thio group or a C 1 to C 5 alkoxy group which is straight-chain or branched and optionally substituted by fluorine, chlorine, bromine, iodine, C 1 to C 5 alkoxy and/or C 1 to C 5 alkylthio, or represents a radical of the general formula ##STR69## wherein R 8 and R 9 independently of each other represent a phenyl radical which is optionally substituted by fluorine, bromine, and/or iodine, or represent a straight-chain or branched C 1 to C 5 alkyl, C 2 to C 5 alkenyl or C 2 to C 5 alkinyl group, or wherein R 8 and R 9 , together with the nitrogen atom to which they are bonded, represent a pyrrolidyl radical which is optionally substituted by methyl and/or ethyl, represent a morpholinyl radical which is optionally substituted by methyl, or represent an azacycloheptyl, piperidyl, 3-methyl-piperidyl, 4-methyl-piperidyl, 2-ethyl-piperidyl, 4-ethyl-piperidyl, 2,3-dimethyl-piperidyl, 2,4-dimethyl-piperidyl, 2,5-dimethyl-piperidyl, or 3,5-dimethyl-piperidyl radical.
Claim 2
Dependent Claim
323 words
A trifluoromethyl-phenoxy-phenyl-silicon compound of the general formula ##STR68## in which X 1 and X 2 independently of each other represent a hydrogen, fluorine, chlorine, bromine or iodine atom, Y represents a hydrogen or halogen atom or a cyano or nitro group, n is 0 or 1, m is 0, 1, 2 or 3, p is 0, 1, 2 or 3, X 3 and X 4 independently of each other represent oxygen or a --CO--O-- group, R 1 , R 2 , R 3 and R 4 independently of one another represent a hydrogen atom or a C 1 to C 5 alkyl group, R 5 and R 6 independently of each other represent a C 1 to C 5 alkyl group, and R 7 represents a C 1 to C 5 alkyl or hydroxyl group, a chlorine, bromine, or iodine atom or a C 2 to C 5 alkenoxy, C 2 to C 5 alkinoxy, C 1 to C 5 alkylthio, C 2 to C 5 alkenyl-thio or C 2 to C 5 alkinyl-thio group or a C 1 to C 5 alkoxy group which is straight-chain or branched and optionally substituted by fluorine, chlorine, bromine, iodine, C 1 to C 5 alkoxy and/or C 1 to C 5 alkylthio, or represents a radical of the general formula ##STR69## wherein R 8 and R 9 independently of each other represent a phenyl radical which is optionally substituted by fluorine, bromine, and/or iodine, or represent a straight-chain or branched C 1 to C 5 alkyl, C 2 to C 5 alkenyl or C 2 to C 5 alkinyl group, or wherein R 8 and R 9 , together with the nitrogen atom to which they are bonded, represent a pyrrolidyl radical which is optionally substituted by methyl and/or ethyl, represent a morpholinyl radical which is optionally substituted by methyl, or represent an azacycloheptyl, piperidyl, 3-methyl-piperidyl, 4-methyl-piperidyl, 2-ethyl-piperidyl, 4-ethyl-piperidyl, 2,3-dimethyl-piperidyl, 2,4-dimethyl-piperidyl, 2,5-dimethyl-piperidyl, or 3,5-dimethyl-piperidyl radical.
Claim 3
Dependent Claim
263 words
A compound according to claim 1, in which X 1 and X 2 independently of each other represent a hydrogen or chlorine atom, Y represents a hydrogen or chlorine atom or a cyano or nitro group, m is 0, 1, 2 or 3, n is 0 or 1, p is 0, 1, 2 or 3, X 3 and X 4 independently of each other represent oxygen or a --CO--O-- group, R 1 , R 2 , R 3 and R 4 independently of one another represent a hydrogen atom or a methyl or ethyl group, R 5 and R 6 independently of each other represent a methyl, ethyl, n-propyl, iso-propyl, n-, iso-, sec.- or tert.-butyl group, and R 7 represents a methyl, ethyl, n-propyl, iso-propyl, n-, iso-, sec.- or tert.-butyl or hydroxyl group, a chlorine atom or a methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec.-butoxy, tert.-butoxy, methylthio, ethylthio, propenoxy, propinoxy, propenylthio or propinylthio group which is optionally substituted by fluorine, chlorine, methoxy, ethoxy, methylthio and/or ethylthio or represents a radical of the general formula ##STR70## wherein R 8 and R 9 independently of each other represent an optionally fluorine-substituted and/or chlorine-substituted phenyl, methyl, ethyl, n-propyl, iso-propyl, n-, iso-, sec.- or tert.-butyl, prop-2-enyl, but-2-enyl, prop-2-inyl or but-2-inyl group or wherein R 8 and R 9 , together with the nitrogen atom to which they are bonded, represent a pyrrolidyl radical which is optionally substituted by methyl and/or ethyl, or represent a morpholinyl radical which is optionally substituted by methyl, or represent an aza-cycloheptyl, piperidyl, 3-methyl-piperidyl, 4-methylpiperidyl, 2-ethyl-piperidyl, 4-ethyl-piperidyl, 2,3-dimethylpiperidyl, 2,4-dimethyl-piperidyl, 2,5-dimethyl-piperidyl or 3,5-dimethylpiperidyl radical.
Claim 4
Dependent Claim
11 words
A compound according to claim 1, wherein X 1 is chlorine.
Claim 5
Dependent Claim
12 words
A compound according to claim 3, wherein Y is a 4-nitro group.
Claim 6
Dependent Claim
11 words
A compound according to claim 4, wherein X 2 is hydrogen.
Claim 7
Dependent Claim
11 words
A compound according to claim 4, wherein X 2 is chlorine.
Claim 8
Dependent Claim
10 words
A compound according to claim 5, of the formula ##STR71##
Claim 9
Dependent Claim
10 words
A compound according to claim 5, of the formula ##STR72##
Claim 10
Dependent Claim
10 words
A compound according to claim 1, of the formula ##STR73##
Claim 11
Dependent Claim
10 words
A compound according to claim 6, of the formula ##STR74##
Claim 12
Dependent Claim
10 words
A compound according to claim 1, of the formula ##STR75##
Claim 13
Dependent Claim
24 words
A herbicidal or plant growth regulating composition comprising a herbicidally effective amount or plant growth regulatingly effective amount of a compound of claim 1.
Claim 14
Dependent Claim
24 words
A composition according to claim 12, wherein the compound of claim 1 is present in an amount of 0.1 to 95 percent by weight.
Claim 15
Dependent Claim
27 words
A method of combating weeds which comprises applying to the weeds or to the habitat thereof, a compound according to claim 1 in a herbicidally effective amount.
Claim 16
Dependent Claim
31 words
A method of regulating the growth of plants which comprises applying to the plants, or to the habitat thereof, a plant growth regulatingly effective amount of the compound of claim 1.
Claim 17
Dependent Claim
29 words
A method according to claim 14, wherein the compound of claim 1 is applied to an area of agriculture in an amount of 0.01 to 50 kg per hectare.
Claim 18
Dependent Claim
30 words
A method according to claim 15, wherein the compound according to claim 1, is applied to an area of agriculture in an amount of 0.01 to 50 kg per hectare.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1987-11-06 | 1988-05-07 | 1988-11-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-11-06 | 1992-05-07 | 1992-11-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-11-06 | 1996-05-07 | 1996-11-06 | $7700.00 | Window Closed / Lapsed |