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US4056527A Expired / Lapsed US ⏱️ 0.0 years remaining

Tetrahydro-1,3,5-triazine-2,6-diones

Assignee: Bayer AG
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Filing: 1973-10-18
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Granted: 1977-11-01
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Expires: 1993-10-18
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Abstract

Abstract New tetrahydro-1,3,5-triazine-2,6-dione compounds of the formula ##STR1## in which R 1 is optionally substituted aliphatic or aromatic hydrocarbyl, R 2 is hydrogen, alkyl, cycloalkyl, aralkyl, aryl, hydroxy, alkoxy, acyloxy, or --NR 4 R 5 , R 4 and R 5 are individually hydrogen, alkyl or acyl, optionally substituted with nitrile, hydroxyl and/or halogen, or R 4 and R 5 together represent alkylidene, and R 3 is hydrogen, alkyl, halogenoalkyl, halogen, aryloxy or an --NR 6 R 7 radical wherein R 6 and R 7 individually are selected from hydrogen, alkyl, cycloalkyl, aralkyl, aryl, hydroxyl, amino or alkoxy and R 6 and R 7 together with the nitrogen atom, represent a heterocyclic radical; R 3 , with the proviso that R 2 is other than hydrogen, can also be alkoxy or alkylmercapto.

Inventors

  • 👤 Hans Georg Schlee
  • 👤 Klaus Sasse
  • 👤 Ludwig Eue

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 17:48
CPC Classifications
A; A01; A01N; A01N43/00; A01N43/64; C; C07; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/14; C07D251/16; C07D251/20; C07D251/26; C07D251/30; C07D251/38; C07D251/40; C07D251/42; C07D251/46

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 277 words
1 (3-times amended) Tetrahydro-1,3,5-triazine-2,6-dione compound of the formula ##STR106## wherein R 1 is alkyl of from 1 to 12 carbon atoms, haloalkyl of from 1 to 12 carbon atoms, cycloalkyl of from 5 to 7 ring carbon atoms, carbocyclic aralkyl of up to 12 carbon atoms or carbocyclic aryl of up to 10 carbon atoms, which cycloalkyl, carbocyclic aralkyl or carbocyclic aryl may be substituted with at least one of halogen, alkyl of up to 4 carbon atoms, alkoxy of up to 4 carbon atoms and trifluoromethyl, R 2 is alkoxy or alkanoyloxy of from 1 to 4 carbon atoms, cycloalkyl of from 5 to 7 ring carbon atoms, carbocyclic aralkyl of up to 12 carbon atoms or carbocyclic aryl of up to 10 carbon atoms; or R 2 is --NR 4 R 5 wherein R 4 and R 5 individually represent hydrogen, alkyl of up to 4 carbon atoms or alkanoyl of up to 4 carbon atoms; or R 2 is --NR 4 R 5 wherein R 4 and R 5 together represent alkylidene, of up to 3 carbon atoms, optionally substituted with at least one of carbocyclic aryl, haloaryl, alkoxyaryl and nitroaryl of up to 10 carbon atoms; R 3 is hydrogen, halogen, alkyl of up to 10 carbon atoms, haloalkyl of up to 10 carbon atoms or carbocyclic aryloxy of up to 10 carbon atoms; or R 3 is --N--R 6 R 7 wherein R 6 and R 7 individually are hydrogen, alkyl of up to 4 carbon atoms, carbocyclic aralkyl of up to 7 carbon atoms, hydroxyl, amino, or methoxy; or R 3 is alkoxy or alkylthio of up to 4 carbon atoms.
Claim 2
Dependent Claim 277 words
1 (3-times amended) Tetrahydro-1,3,5-triazine-2,6-dione compound of the formula ##STR106## wherein R 1 is alkyl of from 1 to 12 carbon atoms, haloalkyl of from 1 to 12 carbon atoms, cycloalkyl of from 5 to 7 ring carbon atoms, carbocyclic aralkyl of up to 12 carbon atoms or carbocyclic aryl of up to 10 carbon atoms, which cycloalkyl, carbocyclic aralkyl or carbocyclic aryl may be substituted with at least one of halogen, alkyl of up to 4 carbon atoms, alkoxy of up to 4 carbon atoms and trifluoromethyl, R 2 is alkoxy or alkanoyloxy of from 1 to 4 carbon atoms, cycloalkyl of from 5 to 7 ring carbon atoms, carbocyclic aralkyl of up to 12 carbon atoms or carbocyclic aryl of up to 10 carbon atoms; or R 2 is --NR 4 R 5 wherein R 4 and R 5 individually represent hydrogen, alkyl of up to 4 carbon atoms or alkanoyl of up to 4 carbon atoms; or R 2 is --NR 4 R 5 wherein R 4 and R 5 together represent alkylidene, of up to 3 carbon atoms, optionally substituted with at least one of carbocyclic aryl, haloaryl, alkoxyaryl and nitroaryl of up to 10 carbon atoms; R 3 is hydrogen, halogen, alkyl of up to 10 carbon atoms, haloalkyl of up to 10 carbon atoms or carbocyclic aryloxy of up to 10 carbon atoms; or R 3 is --N--R 6 R 7 wherein R 6 and R 7 individually are hydrogen, alkyl of up to 4 carbon atoms, carbocyclic aralkyl of up to 7 carbon atoms, hydroxyl, amino, or methoxy; or R 3 is alkoxy or alkylthio of up to 4 carbon atoms.
Claim 3
Dependent Claim 52 words
Dione compound as claimed in claim 1 wherein R 1 is alkyl of from 1 to 12 carbon atoms, haloalkyl of from 1 to 12 carbon atoms, cycloalkyl of from 5 to 7 ring carbon atoms, benzyl or phenyl which may be substituted by at least one of chlorine, methylmethoxy and trifluoromethyl.
Claim 4
Dependent Claim 23 words
Dione compound as claimed in claim 1 wherein R 2 is cycloalkyl of from 5 to 7 ring carbon atoms, phenyl or acetyloxy.
Claim 5
Dependent Claim 39 words
Dione compound as claimed in claim 1 wherein R 2 is --NR 4 R 5 wherein R 4 and R 5 individually represent hydrogen, alkyl of up to 4 carbon atoms or alkanoyl of up to 4 carbon atoms.
Claim 6
Dependent Claim 14 words
Dione compound as claimed in claim 4 wherein R 3 is alkoxy or alkylmercapto.
Claim 7
Dependent Claim 19 words
Dione compound as claimed in claim 5 wherein R 1 is branched alkyl of up to 12 carbon atoms.
Claim 8
Dependent Claim 12 words
Dione compound as claimed in claim 6 wherein R 3 is sec-butyl.
Claim 9
Dependent Claim 9 words
Dione compound as claimed in claim 7 designated 1-sec.-butyl-3-amino-4-methylthio-tetrahydro-1,3,5-triazine-2,6-dione.
Claim 10
Dependent Claim 42 words
Dione compound as claimed in claim 1 wherein R 2 is --NR 4 R 5 wherein R 4 and R 5 together represent alkylidene, otpionally substituted with at least one of aryl, haloaryl, alkoxyaryl and nitroaryl of up to 10 carbon atoms.
Claim 11
Dependent Claim 23 words
Dione compound as claimed in claim 1 wherein R 3 is hydrogen, halogen, alkyl, haloalkyl or aryloxy of up to 10 carbon atoms.
Claim 12
Dependent Claim 19 words
Dione comound as claimed in claim 1 wherein R 3 is alkyl of from 1 to 4 carbon atoms.
Claim 13
Dependent Claim 20 words
Dione compound as claimed in claim 1 wherein R 3 is alkoxy or alkylmercapto of up to 6 carbon atoms.
Claim 14
Dependent Claim 24 words
Dione compound as claimed in claim 1 wherein R 2 is --NR 4 R 5 and R 4 and R 5 together represent cycloalkylidene.
Claim 15
Dependent Claim 9 words
Dione compound as claimed in claim 1 designated 1-isopropyl-3-isopropylideneamino-4-methylmercapto-tetrahydro-1,3,5-triazine-2,6-dione.
Claim 16
Dependent Claim 9 words
Dione compound as claimed in claim 1 designated 1-isopropyl-3-amino-4-methylamino-tetrahydro-1,3,5-triazine-2,6-dione.
Claim 17
Dependent Claim 9 words
Dione compound as claimed in claim 1 designated 1-cyclohexyl-3-isopropylideneamino-4-methylmercapto-tetrahydro-1,3,5-triazine-2,6-dione.
Claim 18
Dependent Claim 9 words
Dione compound as claimed in claim 1 designated 1-cyclohexyl-3-amino-4-methylmercapto-tetrahydro-1,3,5-triazine-2,6-dione.
Claim 19
Dependent Claim 9 words
Dione compound as claimed in claim 1 designated 1-isopropyl-3-amino-4-methylmercapto-tetrahydro-1,3,5-triazine-2,6-dione.
Claim 20
Dependent Claim 20 words
Dione compound as claimed in claim 1 wherein R 1 is branched alkyl of from 1 to 12 carbon atoms.

References Cited (Backward Citations)

US3835133A Cited
US3855219A Cited
US3873540A Cited
US3983116A Cited
US3933815A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-10-31 1981-05-02 1981-11-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-10-31 1985-05-02 1985-11-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-10-31 1989-05-02 1989-11-01 $7700.00 Window Closed / Lapsed

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