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US4221584A
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Herbicidal and plant-growth-regulating N-(heterocyclyl)-methylacetanilides
Assignee: Chevron USA Inc
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Filing: 1979-02-09
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Granted: 1980-09-09
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Expires: 1999-02-09
Abstract
Abstract Compounds of the formula ##STR1## wherein R 1 is alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo, R 2 , R 3 and R 4 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo; R 5 and R 6 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, alkoxyalkyl of 2 to 6 carbon atoms, phenyl and phenyl substituted with 1 to 5 of the same or different substituents selected from fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; X is fluoro, bromo, chloro, iodo or alkoxy of 1 to 3 carbon atoms; W and Z are hetero atoms in an aromatic 5-membered ring independently selected from the group consisting of nitrogen, sulfur and oxygen; and n=0, 1 or 2, have herbicidal and plant growth regulating activity.
Inventors
- 👤 Stephen D. Ziman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 08:33
CPC Classifications
C; C07; C07D; C07D275/00; C07D275/02; A; A01; A01N; A01N43/00; A01N43/02; A01N43/24; A01N43/26; A01N43/48; A01N43/50; A01N43/56; A01N43/72; A01N43/74; A01N43/80; C07D261/00; C07D261/02; C07D261/06; C07D261/08; C07D263/00; C07D263/02; C07D263/30; C07D263/32; C07D277/00; C07D277/02; C07D277/20; C07D277/22; C07D277/28
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
252 words
A compound of the formula ##STR22## wherein R 1 is alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo; R 2 ,R 3 and R 4 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo; R 5 and R 6 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms; alkoxyalkyl of 2 to 6 carbon atoms, phenyl and phenyl substituted with 1 to 5 of the same or different substituents selected from fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; X is fluoro, bromo, chloro, iodo or alkoxy of 1 to 3 carbon atoms; W and Z are hetero atoms in an aromatic 5-membered ring wherein Z is nitrogen and W is sulfur or oxygen; and n=0, 1 or 2.
Claim 2
Dependent Claim
252 words
A compound of the formula ##STR22## wherein R 1 is alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo; R 2 ,R 3 and R 4 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo; R 5 and R 6 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms; alkoxyalkyl of 2 to 6 carbon atoms, phenyl and phenyl substituted with 1 to 5 of the same or different substituents selected from fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; X is fluoro, bromo, chloro, iodo or alkoxy of 1 to 3 carbon atoms; W and Z are hetero atoms in an aromatic 5-membered ring wherein Z is nitrogen and W is sulfur or oxygen; and n=0, 1 or 2.
Claim 3
Dependent Claim
15 words
A compound of the formula defined in claim 1 wherein n=1 and X is chloro.
Claim 4
Dependent Claim
28 words
A compound of the formula defined in claim 2 wherein R 1 and R 2 are independently methyl or ethyl and R 3 and R 4 are hydrogen.
Claim 5
Dependent Claim
25 words
A compound of the formula defined in claim 1 wherein R 5 is hydrogen, R 6 is methyl, W is sulfur and Z is nitrogen.
Claim 6
Dependent Claim
9 words
The compound according to claim 4 which is 2-chloro-N-(2-methylthiazol-4-yl)methyl-N-(2,6-dimethylphenyl)acetamide.
Claim 7
Dependent Claim
9 words
The compound according to claim 4 which is 2-chloro-N-(2-methylthiazol-4-yl)methyl-N-(2,6-diethylphenyl)acetamide.
Claim 8
Dependent Claim
9 words
The compound according to claim 4 which is 2-chloro-N-(2-methylthiazol-4-yl)methyl-N-(2-ethyl-6-methylphenyl)acetamide.
Claim 9
Dependent Claim
14 words
A compound according to claim 3 wherein R 1 and R 2 are methyl.
Claim 10
Dependent Claim
9 words
The compound according to claim 8 which is 2-chloro-N-(isoxazol-3-yl)methyl-N-(2,6-dimethylphenyl)acetamide.
Claim 11
Dependent Claim
9 words
The compound according to claim 8 which is 2-chloro-N-(isothiazol-3-yl)methyl-N-(2,6-dimethylphenyl)acetamide.
Claim 12
Dependent Claim
14 words
A compound according to claim 3 wherein R 1 and R 2 are ethyl.
Claim 13
Dependent Claim
20 words
An herbicidal composition comprising an herbicidally effective amount of a compound defined in claim 1 and a biologically inert carrier.
Claim 14
Dependent Claim
27 words
A method for controlling undesirable vegetation which comprises applying to said vegetation or its growth medium an herbicidally effective amount of a compound defined in claim 1.
Claim 15
Dependent Claim
27 words
A method for controlling undesirable vegetation which comprises applying to said vegetation or its growth medium an herbicidally effective amount of the compound defined in claim 5.
Claim 16
Dependent Claim
27 words
A method for controlling undesirable vegetation which comprises applying to said vegetation or its growth medium an herbicidally effective amount of the compound defined in claim 7.
Claim 17
Dependent Claim
22 words
A plant-growth-regulating composition comprising a biologically inert carrier and a plant-growth-regulating amount of the compound of the formula defined in claim 1.
Claim 18
Dependent Claim
29 words
A method for regulating plant growth which comprises applying to said plants or their growth environment a plant-growth-retarding amount of the compound of the formula defined in claim 1.
Claim 19
Dependent Claim
29 words
A method for regulating plant growth which comprises applying to said plants or their growth environment a plant-growth-retarding amount of the compound of the formula defined in claim 5.
Claim 20
Dependent Claim
29 words
A method for regulating plant growth which comprises applying to said plants or their growth environment a plant-growth-retarding amount of the compound of the formula defined in claim 7.
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) | 1983-09-09 | 1984-03-10 | 1984-09-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-09 | 1988-03-10 | 1988-09-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-09 | 1992-03-10 | 1992-09-09 | $7700.00 | Window Closed / Lapsed |