Patent US4268679A successfully refreshed from Google Patents.
← Back to Patent Explorer
US4268679A Expired / Lapsed US ⏱️ 0.0 years remaining

3-[5- or 3-Substituted-5- or 3-isoxazolyl]-1-allyl or alkyl-4-substituted-5-substituted or unsubstituted-2-imidazolidinones

Assignee: Wyeth Holdings LLC
•
Filing: 1980-02-19
•
Granted: 1981-05-19
•
Expires: 2000-02-19
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Disclosed are compounds such as 3-[5-(1,1-dimethylethyl)-3-isoxazolyl]-1-methyl-4-hydroxy-2-imidazolidinone; their control of weeds such as johnsongrass; the process of making them; and intermediates for making them, the compounds being represented by a Formula I: ##STR1## wherein A is ##STR2## where R is an alkyl of up to six carbon atoms; an alkenyl of up to five carbon atoms; an alkynyl of up to five carbon atoms; a cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; a haloalkyl of up to six carbon atoms; --R 4 --O--R 5 , or --R 4 --S--R 5 , where R 4 is an alkylene of up to six carbon atoms and R 5 is an alkyl of up to six carbon atoms; ##STR3## where Z is nitro (NO 2 ), chloro (Cl), bromo (Br), fluoro (F), or R 5 , and n is 0, 1, 2, or 3; R 1 is an alkyl of up to three carbon atoms, or allyl; R 2 is hydroxy (OH), chloro (Cl) or bromo (Br); and R 3 is hydrogen (H), an alkyl of up to four carbon atoms, allyl, or hydroxy (OH).

Inventors

  • 👤 Jerome M. Lavanish

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 10:55
CPC Classifications
C; C07; C07D; C07D413/00; C07D413/02; C07D413/12; C07D261/00; C07D261/02; C07D261/06; C07D261/10; C07D261/14; A; A01; A01N; A01N43/00; A01N43/48; A01N43/50; A01N43/72; A01N43/80

Claims Analysis

Total Claims: 29
Claim 1
Independent Claim 161 words
A compound of Formula I: ##STR32## wherein: A is ##STR33## where R is an alkyl of up to six carbon atoms, an alkenyl of up to five carbon atoms, an alkynyl of of up to five carbon atoms, a cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. a haloalkyl of up to six carbon atoms, --R 4 --O--R 5 or --R 4 --S--R 5 , where R 4 is an alkylene of up to six carbon atoms and R 5 is an alkyl of up to six carbon atoms, or ##STR34## where Z is nitro (NO 2 ), chloro (Cl), bromo (Br), fluoro (F), or R 5 , and n is 0, 1, 2, or 3; R 1 is an alkyl of up to three carbon atoms or allyl; R 2 is hydroxy (OH), chloro (Cl), or bromo (Br); and R 3 is hydrogen (H), an alkyl of up to four carbon atoms, allyl, or hydroxy (OH).
Claim 2
Dependent Claim 161 words
A compound of Formula I: ##STR32## wherein: A is ##STR33## where R is an alkyl of up to six carbon atoms, an alkenyl of up to five carbon atoms, an alkynyl of of up to five carbon atoms, a cycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. a haloalkyl of up to six carbon atoms, --R 4 --O--R 5 or --R 4 --S--R 5 , where R 4 is an alkylene of up to six carbon atoms and R 5 is an alkyl of up to six carbon atoms, or ##STR34## where Z is nitro (NO 2 ), chloro (Cl), bromo (Br), fluoro (F), or R 5 , and n is 0, 1, 2, or 3; R 1 is an alkyl of up to three carbon atoms or allyl; R 2 is hydroxy (OH), chloro (Cl), or bromo (Br); and R 3 is hydrogen (H), an alkyl of up to four carbon atoms, allyl, or hydroxy (OH).
Claim 3
Dependent Claim 13 words
The compound as recited in claim 1, wherein R 2 is hydroxy (OH).
Claim 4
Dependent Claim 12 words
The compound as recited in claim 2, wherein R 3 is methyl.
Claim 5
Dependent Claim 12 words
The compound as recited in claim 3, wherein R 1 is methyl.
Claim 6
Dependent Claim 13 words
The compound as recited in claim 2, wherein R 3 is hydroxy (OH).
Claim 7
Dependent Claim 12 words
The compound as recited in claim 5, wherein R 1 is methyl.
Claim 8
Dependent Claim 12 words
The compound as recited in claim 2, wherein R 3 is hydrogen.
Claim 9
Dependent Claim 12 words
The compound as recited in claim 7, wherein R 1 is methyl.
Claim 10
Dependent Claim 28 words
The compound as recited in claims 1, 2, 3, 4, 5, 6, 7, or 8, wherein R is selected from the group consisting of 1,1-dimethylethyl, 1-methylethyl, and 3-trifluoromethyl.
Claim 11
Dependent Claim 11 words
The compound as recited in claim 1 wherein A is ##STR35##
Claim 12
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-(3-trifluoromethyl-5-isoxazolyl)-4-hydroxy-1,5-dimethyl-2-imidazolidinone.
Claim 13
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-[3-(1-methylethyl)-5-isoxazolyl]-4-hydroxy-1,5-dimethyl-2-imidazolidinone.
Claim 14
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-[3-(1,1-dimethylethyl)-5-isoxazolyl]-4-hydroxy-1,5-dimethyl-2-imidazolidinone.
Claim 15
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-(3-trifluoromethyl-5-isoxazolyl)-4,5-dihydroxy-1-methyl-2-imidazolidinone.
Claim 16
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-(3-trifluoromethyl-5-isoxazolyl)-4-hydroxy-1-methyl-2-imidazolidinone.
Claim 17
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-[3-(1-methylethyl)-5-isoxazolyl]-4,5-dihydroxy-1-methyl-2-imidazolidinone.
Claim 18
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-[3-(1-methylethyl)-5-isoxazolyl]-4-hydroxy-1-methyl-2-imidazolidinone.
Claim 19
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-[3-(1,1-dimethylethyl)-5-isoxazolyl]-4,5-dihydroxy-1-methyl-2-imidazolidinone.
Claim 20
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-[3-(1,1-dimethylethyl)-5-isoxazolyl]-4-hydroxy-1-methyl-2-imidazolidinone.
Claim 21
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-(5-trifluoromethyl-3-isoxazolyl)-4-hydroxy-1,5-dimethyl-2-imidazolidione.
Claim 22
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-[5-(1-methylethyl)-3-isoxazolyl]-4-hydroxy-1,5-dimethyl-2-imidazolidinone.
Claim 23
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-(5-(1,1-dimethylethyl)-3-isoxazolyl)-4-hydroxy-1,5-dimethyl-2-imidazolidinone.
Claim 24
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-(5-trifluoromethyl-3-isoxazolyl)-4,5-dihydroxy-1-methyl-2-imidazolidinone.
Claim 25
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-(5-trifluoromethyl-3-isoxazolyl)-4-hydroxy-1-methyl-2-imidazolidinone.
Claim 26
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-[5-(1-methylethyl)-isoxazolyl]-4,5-dihydroxy-1-methyl-2-imidazolidinone.
Claim 27
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-[5-(1-methylethyl)-3-isoxazolyl]-4-hydroxy-1-methyl-2-imidazolidinone.
Claim 28
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-[5-(1,1-dimethylethyl)-3-isoxazolyl]-4,5-dihydroxy-1-methyl-2-imidazolidinone.
Claim 29
Dependent Claim 10 words
The compound as recited in claim 1, which is 3-[5-(1,1-dimethylethyl)-3-isoxazolyl]-4-hydroxy-1-methyl-2-imidazolidinone.

References Cited (Backward Citations)

US3544582A Cited
US3773780A Cited
US3847935A Cited
JPS5163170A Cited
DE2727586A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-05-18 1984-11-17 1985-05-19 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-05-18 1988-11-17 1989-05-19 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-05-18 1992-11-17 1993-05-19 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag