US4235619A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Method of controlling aquatic weeds and algae
Assignee: Eli Lilly and Co
•
Filing: 1979-03-19
•
Granted: 1980-11-25
•
Expires: 1999-03-19
Abstract
Abstract A method of reducing the vigor of aquatic weeds and algae makes use of a class of 3-phenyl-4(1H)-pyridones and pyridinethiones. The new compounds are characterized by a methyl group on the nitrogen, and usually bear a 5-substituent chosen from a class which is described herein. The phenyl ring may be substituted. The compounds effectively control aquatic weeds and algae, and kill the plants slowly, so that their decomposition does not deplete oxygen in the treated body of water.
Inventors
- 👤 Harold M. Taylor
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 20:51
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/69; A; A01; A01N; A01N43/00; A01N43/34; A01N43/40; C07D213/63; C07D213/68; C07D213/70; C07D213/71; C07D213/78; C07D213/79; C07D213/80; C07D213/84; C07D213/85; C07D213/89
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
477 words
A method of reducing the vigor of aquatic weeds or algae which comprises applying to water infested with or likely to be infested with such weeds or algae an herbicidally or algicidally effective amount of a compond of the formula ##STR19## wherein X represents oxygen or sulfur; R o represents halo, C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted with halo, C 1 -C 4 alkyl monosubstituted with phenyl, cyano or C 1 -C 3 alkoxy, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 1 -C 3 alkanoyloxy, phenyl, nitro, hydroxy, C 1 -C 3 alkoxycarbonyl, --O--R 3 , --S--R 3 , or --SO--R 3 ; R 3 represents C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted with halo, C 1 -C 4 alkyl monosubstituted with phenyl, cyano or C 1 -C 3 alkoxy, phenyl, phenyl monosubstituted with halo, C 1 -C 3 alkyl, C 1 -C 3 alkoxy or nitro, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, or C 2 -C 4 alkenyl; R 1 represents halo, hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted with halo, C 1 -C 4 alkyl monosubstituted with phenyl, cyano or C 1 -C 3 alkoxy, methoxy, or C 2 -C 4 alkenyl; R 2 represents hydrogen, C 1 -C 3 alkoxycarbonyl, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with halo or C 1 -C 3 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkenyl substituted with halo or C 1 -C 3 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted with halo, C 1 -C 3 alkyl or C 1 -C 3 alkoxy, C 4 -C 6 cycloalkenyl, C 4 -C 8 cycloalkylalkyl, phenyl-C 1 -C 3 alkyl, --O--R 4 , --S--R 4 , --SO--R 4 ; or ##STR20## R 4 represents C 1 -C 3 alkyl, C 1 -C 3 alkyl substituted with halo, C 2 -C 3 alkenyl, C 2 -C 3 alkenyl substituted with halo, benzyl, phenyl or phenyl substituted with halo, C 1 -C 3 alkyl or C 1 -C 3 alkoxy; the R 5 groups independently represent halo, C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted with halo, C 1 -C 4 alkyl monosubstituted with phenyl, cyano or C 1 -C 3 alkoxy, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 1 -C 3 alkanoyloxy, hydroxy, C 1 -C 3 alkoxycarbonyl, --O--R 6 , --S--R 6 , or --SO--R 6 ; R 6 represents C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted with halo, or C 1 -C 4 alkyl monosubstituted with phenyl, cyano or C 1 -C 3 alkoxy; n represents 0-2; and the acid addition salts thereof.
Claim 2
Independent Claim
477 words
A method of reducing the vigor of aquatic weeds or algae which comprises applying to water infested with or likely to be infested with such weeds or algae an herbicidally or algicidally effective amount of a compond of the formula ##STR19## wherein X represents oxygen or sulfur; R o represents halo, C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted with halo, C 1 -C 4 alkyl monosubstituted with phenyl, cyano or C 1 -C 3 alkoxy, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 1 -C 3 alkanoyloxy, phenyl, nitro, hydroxy, C 1 -C 3 alkoxycarbonyl, --O--R 3 , --S--R 3 , or --SO--R 3 ; R 3 represents C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted with halo, C 1 -C 4 alkyl monosubstituted with phenyl, cyano or C 1 -C 3 alkoxy, phenyl, phenyl monosubstituted with halo, C 1 -C 3 alkyl, C 1 -C 3 alkoxy or nitro, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, or C 2 -C 4 alkenyl; R 1 represents halo, hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted with halo, C 1 -C 4 alkyl monosubstituted with phenyl, cyano or C 1 -C 3 alkoxy, methoxy, or C 2 -C 4 alkenyl; R 2 represents hydrogen, C 1 -C 3 alkoxycarbonyl, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with halo or C 1 -C 3 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkenyl substituted with halo or C 1 -C 3 alkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl substituted with halo, C 1 -C 3 alkyl or C 1 -C 3 alkoxy, C 4 -C 6 cycloalkenyl, C 4 -C 8 cycloalkylalkyl, phenyl-C 1 -C 3 alkyl, --O--R 4 , --S--R 4 , --SO--R 4 ; or ##STR20## R 4 represents C 1 -C 3 alkyl, C 1 -C 3 alkyl substituted with halo, C 2 -C 3 alkenyl, C 2 -C 3 alkenyl substituted with halo, benzyl, phenyl or phenyl substituted with halo, C 1 -C 3 alkyl or C 1 -C 3 alkoxy; the R 5 groups independently represent halo, C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted with halo, C 1 -C 4 alkyl monosubstituted with phenyl, cyano or C 1 -C 3 alkoxy, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, C 4 -C 8 cycloalkylalkyl, C 1 -C 3 alkanoyloxy, hydroxy, C 1 -C 3 alkoxycarbonyl, --O--R 6 , --S--R 6 , or --SO--R 6 ; R 6 represents C 1 -C 4 alkyl, C 1 -C 4 alkyl substituted with halo, or C 1 -C 4 alkyl monosubstituted with phenyl, cyano or C 1 -C 3 alkoxy; n represents 0-2; and the acid addition salts thereof.
Claim 3
Dependent Claim
20 words
A method of claim 1 wherein the amount of the compound is from about 0.1 kg/ha to about 20 kg/ha.
Claim 4
Dependent Claim
28 words
A method of claim 2 wherein the vigor of aquatic weeds is reduced and the amount of the compound is from about 0.1 kg/ha to about 5 kg/ha.
Claim 5
Dependent Claim
28 words
A method of claim 1 wherein the amount of the compound is from about 0.01 parts per million by weight to about 15 parts per million by weight.
Claim 6
Dependent Claim
36 words
A method of claim 4 wherein the vigor of aquatic weeds is reduced and the amount of the compound is from about 0.1 parts per million by weight to about 2 parts per million by weight.
Claim 7
Dependent Claim
75 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is of the formula ##STR21## wherein X represents oxygen or sulfur; R 10 represents trifluoromethyl, C 1 -C 3 alkyl, halo, methoxy or methylthio; R 11 represents C 1 -C 4 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, phenyl, phenoxy, phenylthio, or phenyl, phenoxyy or phenylthio monosubstituted with trifluoromethyl, C 1 -C 3 alkyl, halo, methoxy or methylthio.
Claim 8
Dependent Claim
55 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is of the formula ##STR22## wherein X represents oxygen or sulfur; q represents 0-1; p represents 0-2; the R 7 , R 8 and R 12 groups independently represent halo, C 1 -C 3 alkyl, trifluoromethyl or C 1 -C 3 alkoxy.
Claim 9
Dependent Claim
15 words
A method of claim 6 wherein the compound is a compound wherein X represents oxygen.
Claim 10
Dependent Claim
15 words
A method of claim 7 wherein the compound is a compound wherein X represents oxygen.
Claim 11
Dependent Claim
29 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is a compound wherein R 1 represents hydrogen, R 0 represents trifluoromethyl, and X represents oxygen.
Claim 12
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 13
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(3-fluorophenyl)-1-methyl-5-phenyl-4(1H)-pyridone.
Claim 14
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(3-chlorophenyl)-1-methyl-5-phenyl-4(1H)-pyridone.
Claim 15
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3,5-bis(3-chlorophenyl)-1-methyl-4(1H)-pyridone.
Claim 16
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(3-chlorophenyl)-5-(3-fluorophenyl)-1-methyl-4(1H)-pyridone.
Claim 17
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 1-methyl-3-(3-methylphenyl)-5-phenyl-4(1H)-pyridone.
Claim 18
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(3-bromophenyl)-1-methyl-5-phenyl-4(1H)-pyridone.
Claim 19
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(3-methoxyphenyl)-1-methyl-5-phenyl-4(1H)-pyridone.
Claim 20
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3,5-bis(3-fluorophenyl)-1-methyl-4(1H)-pyridone.
Claim 21
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(2-chlorophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 22
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(4-chlorophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 23
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(2-fluorophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 24
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(4-fluorophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 25
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-ethyl-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 26
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 1-methyl-3-(3-methylthiophenyl)-5-phenyl-4(1H)-pyridone.
Claim 27
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(4-chloro-3-trifluoromethylphenyl)-1-methyl-5-phenyl-4(1H)-pyridone.
Claim 28
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(3-bromophenyl)-5-(3-chlorophenyl)-1-methyl-4(1H)-pyridone.
Claim 29
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(2-bromophenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 30
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 1-methyl-3-(2-methylphenyl)-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 31
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(2-methoxyphenyl)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 32
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(3-isobutylphenyl)-1-methyl-5-phenyl-4(1H)-pyridone.
Claim 33
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 1-methyl-3-propyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 34
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-ethoxy-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 35
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-isopropoxy-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 36
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(4-chloro-3-trifluoromethylphenyl)-5-ethoxy-1-methyl-4(1H)-pyridone.
Claim 37
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 1-methyl-3-(4-chloro-3-trifluoromethylphenyl)-5-propyl-4(1H)-pyridone.
Claim 38
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-ethyl-1-methyl-5-(4-chloro-3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 39
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-ethylthio-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 40
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 1-methyl-3-propylthio-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 41
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 1-methyl-3-isopropylthio-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 42
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 1-methyl-3-(3-trifluoromethylphenyl)-5-trifluoromethylthio-4(1H)-pyridone.
Claim 43
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-isopropyl-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 44
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 3-(3,5-dichlorophenoxy)-1-methyl-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
Claim 45
Dependent Claim
15 words
A method of claim 1, 2, 3, 4 or 5 wherein the compound is 1-methyl-3-(2,2,2-trifluoroethoxy)-5-(3-trifluoromethylphenyl)-4(1H)-pyridone.
References Cited (Backward Citations)
US3244722A
Cited
US4116665A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-11-25 | 1984-05-26 | 1984-11-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-25 | 1988-05-26 | 1988-11-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-25 | 1992-05-26 | 1992-11-25 | $7700.00 | Window Closed / Lapsed |