US3983116A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Herbicidal triazines
Assignee: EIDP Inc
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Filing: 1974-06-05
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Granted: 1976-09-28
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Expires: 1994-06-05
Abstract
Abstract Compounds of the formula: ##SPC1## Wherein X is oxygen or sulfur; R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylmethyl, cycloalkenylmethyl, bicycloalkyl, bicycloalkenyl, bicycloalkylmethyl, bicycloalkenylmethyl, phenyl, substituted alkyl, substituted cycloalkyl, or substituted phenyl; R 2 is hydrogen or alkyl; R 3 is H, methyl, or ethyl; and R 4 is alkyl, alkenyl, alkynyl, or methoxy; and the salts with bases of those compounds wherein R 2 is hydrogen, are useful as herbicides. A preferred compound is 1-methyl-3-cyclohexyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione.
Inventors
- 👤 Kang Lin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 05:13
CPC Classifications
C; C07; C07C; C07C335/00; C07C335/30; C07C335/38
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
254 words
A compound of the formula: ##SPC9## wherein R 1 is selected from alkyl of 2 through 8 carbon atoms, alkenyl of 3 through 6 carbon atoms, alkynyl of 3 through through 6 carbon atoms, cycloalkyl of 4 through 8 carbon atoms, cycloalkenyl of 5 through 8 carbon atoms, cycloalkylmethyl of 4 through 9 carbon atoms, cycloalkenylmethyl of 6 through 9 carbon atoms, bicycloalkyl or bicycloalkenyl of 7 through 10 carbon atoms and bicycloalkylmethyl or bicycloalkenylmethyl of 8 through 11 carbon atoms, trimethylcyclohexyl and tetramethylcyclohexyl; the above alkyl groups substituted with one methoxy, ethoxy, methylthio or ethylthio group; the above cycloalkyl groups substituted with one alkyl of 2 through 4 carbon atoms, 1 through 2 methyl groups, 1 through 2 chlorines or bromines, one methoxy or one ethoxy group; and ##SPC10## wherein Q is hydrogen, fluorine, chlorine, bromine, alkyl of 1 through 4 carbon atoms, alkoxy or alkylthio of 1 through 2 carbon atoms, nitro or a trifluoromethyl group; Y is hydrogen, chlorine, or methyl; and Z is hydrogen or chlorine; R 2 is hydrogen, alkyl of 1 through 3 carbon atoms or a cation selected from Na + , Li + , K + , (Ca/2) + , ammonium and dimethylammonium; R 3 is hydrogen, methyl or ethyl; R 4 is alkyl of 1 through 4 carbon atoms, alkenyl of 3 through 4 carbon atoms, alkynyl of 3 through 4 carbon atoms, or methoxy; and X is oxygen or sulfur; provided that when X is sulfur, neither R 2 nor R 3 is hydrogen.
Claim 2
Dependent Claim
254 words
A compound of the formula: ##SPC9## wherein R 1 is selected from alkyl of 2 through 8 carbon atoms, alkenyl of 3 through 6 carbon atoms, alkynyl of 3 through through 6 carbon atoms, cycloalkyl of 4 through 8 carbon atoms, cycloalkenyl of 5 through 8 carbon atoms, cycloalkylmethyl of 4 through 9 carbon atoms, cycloalkenylmethyl of 6 through 9 carbon atoms, bicycloalkyl or bicycloalkenyl of 7 through 10 carbon atoms and bicycloalkylmethyl or bicycloalkenylmethyl of 8 through 11 carbon atoms, trimethylcyclohexyl and tetramethylcyclohexyl; the above alkyl groups substituted with one methoxy, ethoxy, methylthio or ethylthio group; the above cycloalkyl groups substituted with one alkyl of 2 through 4 carbon atoms, 1 through 2 methyl groups, 1 through 2 chlorines or bromines, one methoxy or one ethoxy group; and ##SPC10## wherein Q is hydrogen, fluorine, chlorine, bromine, alkyl of 1 through 4 carbon atoms, alkoxy or alkylthio of 1 through 2 carbon atoms, nitro or a trifluoromethyl group; Y is hydrogen, chlorine, or methyl; and Z is hydrogen or chlorine; R 2 is hydrogen, alkyl of 1 through 3 carbon atoms or a cation selected from Na + , Li + , K + , (Ca/2) + , ammonium and dimethylammonium; R 3 is hydrogen, methyl or ethyl; R 4 is alkyl of 1 through 4 carbon atoms, alkenyl of 3 through 4 carbon atoms, alkynyl of 3 through 4 carbon atoms, or methoxy; and X is oxygen or sulfur; provided that when X is sulfur, neither R 2 nor R 3 is hydrogen.
Claim 3
Dependent Claim
52 words
A compound of claim 1 wherein: R 1 is alkyl of 3 through 6 carbon atoms, cycloalkyl of 5 through 8 carbon atoms, or cycloalkyl of 5 through 8 carbon atoms substituted with one methyl group; R 2 , r 3 and R 4 are methyl; and X is oxygen or sulfur.
Claim 4
Dependent Claim
56 words
A compound of claim 1 wherein: R 1 is alkyl of 3 through 6 carbon atoms; cycloalkyl of 5 through 8 carbon atoms; cyclopentyl substituted with one methyl group; cyclohexyl substituted with 1 or 2 methyl groups; 3-trifluoromethylphenyl; cyclohexenyl; or decahydronaphthen-1-yl; R 2 and R 3 are methyl; R 4 is hydrogen; and X is oxygen.
Claim 5
Dependent Claim
49 words
A compound of claim 1 wherein: R 1 is cyclohexyl substituted with two methyl groups; 3-trifluoromethylphenyl; cyclohexenyl; decahydronaphthen-1-yl; or ##SPC11## where P is hydrogen, methyl, chlorine, or fluorine, and Q is hydrogen or chlorine; R 2 , r 3 , and R 4 are methyl; and X is oxygen.
Claim 6
Dependent Claim
37 words
A compound of claim 3 wherein: R 1 is alkyl of 3 through 4 carbon atoms; neopentyl; 1-ethylpropyl; n-hexyl; cycloalkyl of 5 through 8 carbon atoms; 2-methylcyclohexyl; 3-methylcyclohexyl; 2,3-dimethylcyclohexyl; 3,4-dimethylcyclohexyl; 2,4-dimethylcyclohexyl; 2,6-dimethylcyclohexyl; 3,5-dimethylcyclohexyl; 3-trifluoromethylphenyl; 3-cyclohexen-1-yl; or 1-decahydronaphthyl.
Claim 7
Dependent Claim
30 words
A compound of claim 4 wherein: R 1 is 2,4-dimethylcyclohexyl; 2,6-dimethylcyclohexyl; 2,3-dimethylcyclohexyl; 3,4-dimethylcyclohexyl; 3-trifluoromethylphenyl; 3-cyclohexen-1-yl; 1-decahydronaphthyl; phenyl; 3-methyl phenyl; 4-methylphenyl; 3,4-dichlorophenyl; 2,5-dichlorophenyl; 2-chlorophenyl; 3-chlorophenyl; 4-chlorophenyl; 2-fluorophenyl; 3-fluorophenyl; 2-methyl-5-chlorophenyl; or 3-chloro-4-methylphenyl.
Claim 8
Dependent Claim
29 words
A compound of claim 1 wherein: R 1 is cyclopentyl, methylcyclopentyl, cyclohexyl, or methylcyclohexyl; R 2 , r 3 , and R 4 are methyl; and X is oxygen.
Claim 9
Dependent Claim
5 words
Compound of claim 1: 1-Methyl-3-cyclohexyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione.
Claim 10
Dependent Claim
5 words
Compound of claim 1: 1-Methyl-3-cyclopentyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione.
Claim 11
Dependent Claim
17 words
A compound of claim 1 wherein R 2 , R 3 and R 4 are all methyl.
Claim 12
Dependent Claim
198 words
A compound of claim 10 wherein R 1 is selected from: alkyl of 2 through 8 carbon atoms, alkenyl of 3 through 6 carbon atoms, alkynyl of 3 through 6 carbon atoms, cycloalkyl of 4 through 8 carbon atoms, cycloalkenyl of 5 through 8 carbon atoms, cycloalkylmethyl of 5 through 9 carbon atoms, cycloalkenylmethyl of 6 through 9 carbon atoms, bicycloalkyl of 7 through 10 carbon atoms, bicycloalkenyl of 7 through 10 carbon atoms, bicycloalkylmethyl of 8 carbon atoms, bicycloalkenylmethyl of 8 through 11 carbon atoms, trimethylcyclohexyl, and tetramethylcyclohexyl; and alkyl of 2 through 3 carbon atoms substituted with one methoxy, ethoxy, methylthio or ethylthio group, cycloalkyl of 5 through 6 carbon atoms substituted with one methyl or two chloro groups, cyclobutyl substituted with one chloro group, and cyclohexyl substituted with one alkyl group of 2 through 4 carbon atoms, two methyl groups, one chloro group, one bromo group, one methoxy group or one ethoxy group; and ##SPC12## wherein Q is hydrogen, fluorine, chlorine, bromine, alkyl of 1 through 4 carbon atoms, alkoxy or alkylthio of 1 through 2 carbon atoms, nitro or a trifluoromethyl group; Y is hydrogen, chlorine, or methyl; and Z is hydrogen or chlorine.
References Cited (Backward Citations)
GB814948A
Cited
DE2254200A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-09-28 | 1980-03-29 | 1980-09-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-28 | 1984-03-29 | 1984-09-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-28 | 1988-03-29 | 1988-09-28 | $7700.00 | Window Closed / Lapsed |