Patent US4130413A successfully refreshed from Google Patents.
US4130413A
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Heterocyclic phenyl ethers and herbicides containing same
Assignee: Hoechst AG
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Filing: 1977-09-08
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Granted: 1978-12-19
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Expires: 1997-09-08
Abstract
Abstract Compounds of the formula ##STR1## in which (R) n is hydrogen, halogen, CF 3 , NO 2 , CN, alkyl, alkoxy or alkylthio, A is O, S, NH, or N-alkyl, R 1 is hydrogen or alkyl and Z is a carboxylic acid, carboxylic ester, thiol ester, carbonamide, carbohydrazide, thioamide, nitrile, hydroxymethyl, acyloxymethyl, carbamoylmethyl, or sulfonyloxymethyl group, Are valuable herbicides for the selective control of weed grasses. The novel compounds are prepared by known methods, for example by reacting halo-benzthiazoles, -benzoxazoles or -benzimidazoles with unilaterally etherified hydroquinones.
Inventors
- 👤 Reinhard Handte
- 👤 Gerhard Horlein
- 👤 Helmut Kocher
- 👤 Peter Langeluddeke
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 08:34
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/63; C07D213/64; C07D213/643; A; A01; A01N; A01N39/00; A01N39/02; A01N43/00; A01N43/02; A01N43/04; A01N43/06; A01N43/08; A01N43/20; A01N43/34; A01N43/40; A01N43/48; A01N43/50; A01N43/52; A01N43/72; A01N43/74; A01N43/76; A01N43/78; A01N47/00; A01N47/08; A01N47/10; A01N47/12; A01N47/16; A01N47/18; A01N47/20; C07C; C07C243/00; C07C59/00; C07C59/40; C07C59/58; C07C59/64; C07C59/66; C07C59/68; C07D235/00; C07D235/02; C07D235/04; C07D235/24; C07D235/26; C07D263/00; C07D263/52; C07D263/54; C07D263/58; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D307/00; C07D307/02; C07D307/04; C07D307/10; C07D307/12
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
486 words
A compound of the formula ##STR88## in which R is halogen, CF 3 , NO 2 , CN, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio, A is O, S, NH, or N--(C 1 -C 4 )alkyl, R 1 is H or C 1 -C 4 alkyl, Z is a group of the formula ##STR89## n is zero or 1 or 2, R 2 is H, C 1 -C 12 alkyl (optionally substituted by 1 to 6 halogen atoms), OH, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio, C 1 -C 6 alkoxy-C 2 -C 6 alkoxy, halo-C 1 -C 2 alkoxy, methoxyethoxy-ethoxy, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, phenyl, oxiranyl and/or phenoxy which latter may be substituted once or twice by halogen or C 1 -C 4 alkyl; C 5 -C 6 cycloalkyl (optionally substituted by halogen or methyl); C 3 -C 6 alkenyl, halo-C 3 -C 6 -alkenyl or C 5 -C 6 cycloalkenyl, C 3 -C 4 alkinyl (optionally substituted once or twice by C 1 -C 6 alkyl, phenyl, halogen or C 1 -C 2 alkoxy); phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, NO 2 , or CF 3 ); furfuryl, tetrahydrofurfuryl, or the cation equivalent of an organic or inorganic base; R 3 is C 1 -C 6 alkyl, phenyl-(C 1 -C 2 )-alkyl, the phenyl radical optionally being substituted once or twice by C 1 -C 4 alkyl and/or halogen, C 3 -C 6 alkenyl, or phenyl (optionally substituted once or twice by C 1 -C 4 alkyl and/or halogen) R 4 and R 5 ; which are identical or different, are H, C 1 -C 6 alkyl, hydroxy-(C 1 -C 6 )-alkyl, C 5 -C 6 cycloalkyl, or phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, or CF 3 ), with the proviso that R 4 and R 5 cannot be phenyl at the same time; or wherein R 4 and R 5 together form a methylene chain having 2,4 or 5 CH 2 -groups in which one CH 2 group may be replaced by O, NH, or N(CH 3 ); R 6 is H or CH 3 , R 7 is H, CH 3 , or C 2 H 5 , R 8 is H, CH 3 , C 3 H 5 or phenyl, R 9 is C 1 -C 6 alkyl (optionally substituted one to three times by halogen), cyclopropyl, C 3 -C 6 alkenyl, phenyl, C 1 -C 4 alkylphenyl C 1 -C 4 alkoxyphenyl, halophenyl, trifluoromethylphenyl or nitrophenyl and R 10 is C 1 -C 4 alkyl or phenyl (optionally substituted once or twice by halogen, CF 3 , NO 2 , or C 1 -C 4 alkyl).
Claim 2
Dependent Claim
486 words
A compound of the formula ##STR88## in which R is halogen, CF 3 , NO 2 , CN, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio, A is O, S, NH, or N--(C 1 -C 4 )alkyl, R 1 is H or C 1 -C 4 alkyl, Z is a group of the formula ##STR89## n is zero or 1 or 2, R 2 is H, C 1 -C 12 alkyl (optionally substituted by 1 to 6 halogen atoms), OH, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio, C 1 -C 6 alkoxy-C 2 -C 6 alkoxy, halo-C 1 -C 2 alkoxy, methoxyethoxy-ethoxy, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, phenyl, oxiranyl and/or phenoxy which latter may be substituted once or twice by halogen or C 1 -C 4 alkyl; C 5 -C 6 cycloalkyl (optionally substituted by halogen or methyl); C 3 -C 6 alkenyl, halo-C 3 -C 6 -alkenyl or C 5 -C 6 cycloalkenyl, C 3 -C 4 alkinyl (optionally substituted once or twice by C 1 -C 6 alkyl, phenyl, halogen or C 1 -C 2 alkoxy); phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, NO 2 , or CF 3 ); furfuryl, tetrahydrofurfuryl, or the cation equivalent of an organic or inorganic base; R 3 is C 1 -C 6 alkyl, phenyl-(C 1 -C 2 )-alkyl, the phenyl radical optionally being substituted once or twice by C 1 -C 4 alkyl and/or halogen, C 3 -C 6 alkenyl, or phenyl (optionally substituted once or twice by C 1 -C 4 alkyl and/or halogen) R 4 and R 5 ; which are identical or different, are H, C 1 -C 6 alkyl, hydroxy-(C 1 -C 6 )-alkyl, C 5 -C 6 cycloalkyl, or phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, or CF 3 ), with the proviso that R 4 and R 5 cannot be phenyl at the same time; or wherein R 4 and R 5 together form a methylene chain having 2,4 or 5 CH 2 -groups in which one CH 2 group may be replaced by O, NH, or N(CH 3 ); R 6 is H or CH 3 , R 7 is H, CH 3 , or C 2 H 5 , R 8 is H, CH 3 , C 3 H 5 or phenyl, R 9 is C 1 -C 6 alkyl (optionally substituted one to three times by halogen), cyclopropyl, C 3 -C 6 alkenyl, phenyl, C 1 -C 4 alkylphenyl C 1 -C 4 alkoxyphenyl, halophenyl, trifluoromethylphenyl or nitrophenyl and R 10 is C 1 -C 4 alkyl or phenyl (optionally substituted once or twice by halogen, CF 3 , NO 2 , or C 1 -C 4 alkyl).
Claim 3
Dependent Claim
8 words
2-[4'-(5"-Chlorobenzoxazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl esters.
Claim 4
Dependent Claim
8 words
2-[4'-(5"-Chlorobenzoxazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl esters.
Claim 5
Dependent Claim
8 words
2-[4'-(6"-Chlorobenzoxazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl esters.
Claim 6
Dependent Claim
8 words
2-[4'-(6"-Chlorobenzoxazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl esters.
Claim 7
Dependent Claim
8 words
2-[4'-(6"-Chlorobenzthiazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl esters.
Claim 8
Dependent Claim
8 words
2-[4'-(6"-Chlorobenzthiazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl esters.
Claim 9
Dependent Claim
8 words
2-[4'-(6"-Bromobenzthiazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl esters.
Claim 10
Dependent Claim
8 words
2-[4'-(6"-Bromobenzthiazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl esters.
Claim 11
Dependent Claim
8 words
2-[4'-(5"-Chlorobenzthiazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl ester.
Claim 12
Dependent Claim
8 words
2-[4'-(5"-Chlorobenzthiazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl ester.
Claim 13
Dependent Claim
8 words
2-[4'-(5"-Methylbenzthiazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl esters.
Claim 14
Dependent Claim
8 words
2-[4'-(5"-Methylbenzthiazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 )alkyl esters.
Claim 15
Dependent Claim
9 words
2-[4'-(benzthiazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 ) alkyl esters,
Claim 16
Dependent Claim
9 words
2-[4'-(benzthiazolyl-2"-oxy)-phenoxy]-propionic acid (C 1 -C 4 ) alkyl esters,
Claim 17
Dependent Claim
2 words
2-[4'-(Benzthiazolyl-2"-oxy)-phenoxy]-propanol 1.
Claim 18
Dependent Claim
2 words
2-[4'-(Benzthiazolyl-2"-oxy)-phenoxy]-propanol 1.
Claim 19
Dependent Claim
1 words
2-[4'-(5"-Chlorobenzoxazolyl-2"-oxy)-phenoxy]-propanol-1.
Claim 20
Dependent Claim
1 words
2-[4'-(5"-Chlorobenzoxazolyl-2"-oxy)-phenoxy]-propanol-1.
Claim 21
Dependent Claim
1 words
2-[4'-(6"-Chlorobenzoxyzolyl-2"-oxy)-phenoxy]-propanol-1.
Claim 22
Dependent Claim
1 words
2-[4'-(6"-Chlorobenzoxyzolyl-2"-oxy)-phenoxy]-propanol-1.
Claim 23
Dependent Claim
1 words
2-[4'-(6"-Chlorobenzoxyzolyl-2"-oxy)-phenoxy]-propanol-1.
Claim 24
Dependent Claim
1 words
2-[4'-(6"-Chlorobenzoxyzolyl-2"-oxy)-phenoxy]-propanol-1.
Claim 25
Dependent Claim
1 words
2-[4'-(6"-Bromobenzthiazolyl-2"-oxy)-phenoxy]-propanol-1.
Claim 26
Dependent Claim
1 words
2-[4'-(6"-Bromobenzthiazolyl-2"-oxy)-phenoxy]-propanol-1.
Claim 27
Dependent Claim
502 words
An herbicidal composition consisting essentially of an inert carrier and an herbicidally effective amount of a compound of the formula ##STR90## in which R is halogen, CF 3 , NO 2 , CN, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio, A is O, S, NH, or N-(C 1 -C 4 )alkyl, R 1 is H or C 1 -C 4 alkyl, Z is a group of the formula ##STR91## n is zero or 1 or 2, R 2 is H, C 1 -C 12 alkyl (optionally substituted by 1 to 6 halogen atoms, OH, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio, C 1 -C 6 alkoxy-C 2 -C 6 alkoxy, halo-C 1 -C 2 alkoxy, methoxyethoxy-ethoxy, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, phenyl, oxiranyl and/or phenoxy which latter may be substituted once or twice by halogen or C 1 -C 4 alkyl); C 5 -C 6 cycloalkyl (optionally substituted by halogen or methyl); C 3 -C 6 alkenyl, halo-C 3 -C 6 alkenyl or C 5 -C 6 cycloalkenyl, C 3 -C 4 -alkinyl (optionally substituted once or twice by C 1 -C 6 alkyl, phenyl, halogen or C 1 -C 2 alkoxy); phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, NO 2 , or CF 3 ); furfuryl, tetrahydrofurfuryl, or the cation equivalent of an organic or inorganic base; R 3 is C 1 -C 6 alkyl, phenyl-(C 1 -C 2 )-alkyl, the phenyl radical optionally being substituted once or twice by C 1 -C 4 alkyl and/or halogen, C 3 -C 6 alkenyl, or phenyl (optionally substituted once or twice by C 1 -C 4 alkyl and/or halogen), R 4 and R 5 , which are identical or different, are H, C 1 -C 6 alkyl, hydroxy-(C 1 -C 6 )-alkyl, C 5 -C 6 cycloalkyl, or phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen or CF 3 ), with the proviso that R 4 and R 5 cannot be phenyl at the same time; or wherein R 4 and R 5 together form a methylene chain having 2, 4 or 5 CH 2 -groups in which one CH 2 group may be replaced by O, NH, or N(CH 3 ); R 6 is H or CH 3 , R 7 is H, CH 3 , or C 2 H 5 , R 8 is H, CH 3 , C 2 H 5 or phenyl, R 9 is C 1 -C 6 alkyl (optionally substituted one to three times by halogen), cyclopropyl, C 3 -C 6 alkenyl, phenyl, C 1 -C 4 alkylphenyl C 1 -C 4 alkoxyphenyl, halophenyl, trifluoromethylphenyl or nitrophenyl and R 10 is C 1 -C 4 alkyl or phenyl (optionally substituted once or twice by halogen, CF 3 , NO 2 , or C 1 -C 4 alkyl).
Claim 28
Dependent Claim
502 words
An herbicidal composition consisting essentially of an inert carrier and an herbicidally effective amount of a compound of the formula ##STR90## in which R is halogen, CF 3 , NO 2 , CN, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio, A is O, S, NH, or N-(C 1 -C 4 )alkyl, R 1 is H or C 1 -C 4 alkyl, Z is a group of the formula ##STR91## n is zero or 1 or 2, R 2 is H, C 1 -C 12 alkyl (optionally substituted by 1 to 6 halogen atoms, OH, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio, C 1 -C 6 alkoxy-C 2 -C 6 alkoxy, halo-C 1 -C 2 alkoxy, methoxyethoxy-ethoxy, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, phenyl, oxiranyl and/or phenoxy which latter may be substituted once or twice by halogen or C 1 -C 4 alkyl); C 5 -C 6 cycloalkyl (optionally substituted by halogen or methyl); C 3 -C 6 alkenyl, halo-C 3 -C 6 alkenyl or C 5 -C 6 cycloalkenyl, C 3 -C 4 -alkinyl (optionally substituted once or twice by C 1 -C 6 alkyl, phenyl, halogen or C 1 -C 2 alkoxy); phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, NO 2 , or CF 3 ); furfuryl, tetrahydrofurfuryl, or the cation equivalent of an organic or inorganic base; R 3 is C 1 -C 6 alkyl, phenyl-(C 1 -C 2 )-alkyl, the phenyl radical optionally being substituted once or twice by C 1 -C 4 alkyl and/or halogen, C 3 -C 6 alkenyl, or phenyl (optionally substituted once or twice by C 1 -C 4 alkyl and/or halogen), R 4 and R 5 , which are identical or different, are H, C 1 -C 6 alkyl, hydroxy-(C 1 -C 6 )-alkyl, C 5 -C 6 cycloalkyl, or phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen or CF 3 ), with the proviso that R 4 and R 5 cannot be phenyl at the same time; or wherein R 4 and R 5 together form a methylene chain having 2, 4 or 5 CH 2 -groups in which one CH 2 group may be replaced by O, NH, or N(CH 3 ); R 6 is H or CH 3 , R 7 is H, CH 3 , or C 2 H 5 , R 8 is H, CH 3 , C 2 H 5 or phenyl, R 9 is C 1 -C 6 alkyl (optionally substituted one to three times by halogen), cyclopropyl, C 3 -C 6 alkenyl, phenyl, C 1 -C 4 alkylphenyl C 1 -C 4 alkoxyphenyl, halophenyl, trifluoromethylphenyl or nitrophenyl and R 10 is C 1 -C 4 alkyl or phenyl (optionally substituted once or twice by halogen, CF 3 , NO 2 , or C 1 -C 4 alkyl).
Claim 29
Independent Claim
508 words
A method for controlling the growth of undesired weed grasses which comprises treating the infested area with an herbicidally effective amount of a compound of the formula ##STR92## in which R is halogen, CF 3 , NO 2 , CN, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio, A is O, S, NH, or N-(C 1 -C 4 )alkyl, R is H or C 1 -C 4 alkyl, Z is a group of the formula ##STR93## n is zero or 1 or 2, R 2 is H, C 1 -C 12 alkyl (optionally substituted by 1 to 6 halogen atoms), OH, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio, C 1 -C 6 alkoxy-C 2 -C 6 -alkoxy, halo-C 1 -C 2 alkoxy, methoxyethoxy-ethoxy, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, phenyl, oxiranyl and/or phenoxy which latter may be substituted once or twice by halogen or C 1 -C 4 alkyl; C 5 -C 6 cycloalkyl (optionally substituted by halogen or methyl); C 3 -C 6 alkenyl, halo-C 3 -C 6 alkenyl or C 5 -C 6 cycloalkenyl, C 3 -C 4 alkinyl (optionally substituted once or twice by C 1 -C 6 alkyl, phenyl, halogen or C 1 -C 2 alkoxy); phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen NO 2 , or CF 3 ); furfuryl, tetrahydrofurfuryl, or the cation equivalent of an organic or inorganic base; R 3 is C 1 -C 6 alkyl, phenyl-(C 1 -C 2 )-alkyl, the phenyl radical optionally being substituted once or twice by C 1 -C 4 alkyl and/or halogen, C 3 -C 6 alkenyl, or phenyl (optionally substituted once or twice by C 1 -C 4 alkyl and/or halogen); R 4 and R 5 , which are identical or different, are H, C 1 -C 6 alkyl, hydroxy-(C 1 -C 6 )-alkyl, C 5 -C 6 cycloalkyl, or phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen or CF 3 ), with the proviso that R 4 and R 5 cannot be phenyl at the same time; or wherein R 4 and R 5 together form a methylene chain having 2, 4 or 5 CH 2 -groups in which one CH 2 group may be replaced by O, NH, or N(CH 3 ); R 6 is H or CH 3 , R 7 is H, CH 3 , or C 2 H 5 , R 8 is H, CH 3 , C 3 H 5 or phenyl, R 9 is C 1 -C 6 alkyl (optionally substituted one to three times by halogen), cyclopropyl, C 3 -C 6 alkenyl, phenyl, C 1 -C 4 alkylphenyl C 1 -C 4 alkoxyphenyl, halophenyl, trifluoromethylphenyl or nitrophenyl and R 10 is C 1 -C 4 alkyl or phenyl (optionally substituted once or twice by halogen, CF 3 , NO 2 , or C 1 -C 4 alkyl).
Claim 30
Independent Claim
508 words
A method for controlling the growth of undesired weed grasses which comprises treating the infested area with an herbicidally effective amount of a compound of the formula ##STR92## in which R is halogen, CF 3 , NO 2 , CN, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio, A is O, S, NH, or N-(C 1 -C 4 )alkyl, R is H or C 1 -C 4 alkyl, Z is a group of the formula ##STR93## n is zero or 1 or 2, R 2 is H, C 1 -C 12 alkyl (optionally substituted by 1 to 6 halogen atoms), OH, C 1 -C 6 alkoxy, C 1 -C 4 alkylthio, C 1 -C 6 alkoxy-C 2 -C 6 -alkoxy, halo-C 1 -C 2 alkoxy, methoxyethoxy-ethoxy, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, phenyl, oxiranyl and/or phenoxy which latter may be substituted once or twice by halogen or C 1 -C 4 alkyl; C 5 -C 6 cycloalkyl (optionally substituted by halogen or methyl); C 3 -C 6 alkenyl, halo-C 3 -C 6 alkenyl or C 5 -C 6 cycloalkenyl, C 3 -C 4 alkinyl (optionally substituted once or twice by C 1 -C 6 alkyl, phenyl, halogen or C 1 -C 2 alkoxy); phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen NO 2 , or CF 3 ); furfuryl, tetrahydrofurfuryl, or the cation equivalent of an organic or inorganic base; R 3 is C 1 -C 6 alkyl, phenyl-(C 1 -C 2 )-alkyl, the phenyl radical optionally being substituted once or twice by C 1 -C 4 alkyl and/or halogen, C 3 -C 6 alkenyl, or phenyl (optionally substituted once or twice by C 1 -C 4 alkyl and/or halogen); R 4 and R 5 , which are identical or different, are H, C 1 -C 6 alkyl, hydroxy-(C 1 -C 6 )-alkyl, C 5 -C 6 cycloalkyl, or phenyl (optionally substituted one to three times by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen or CF 3 ), with the proviso that R 4 and R 5 cannot be phenyl at the same time; or wherein R 4 and R 5 together form a methylene chain having 2, 4 or 5 CH 2 -groups in which one CH 2 group may be replaced by O, NH, or N(CH 3 ); R 6 is H or CH 3 , R 7 is H, CH 3 , or C 2 H 5 , R 8 is H, CH 3 , C 3 H 5 or phenyl, R 9 is C 1 -C 6 alkyl (optionally substituted one to three times by halogen), cyclopropyl, C 3 -C 6 alkenyl, phenyl, C 1 -C 4 alkylphenyl C 1 -C 4 alkoxyphenyl, halophenyl, trifluoromethylphenyl or nitrophenyl and R 10 is C 1 -C 4 alkyl or phenyl (optionally substituted once or twice by halogen, CF 3 , NO 2 , or C 1 -C 4 alkyl).
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) | 1981-12-18 | 1982-06-19 | 1982-12-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-18 | 1986-06-19 | 1986-12-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-18 | 1990-06-19 | 1990-12-19 | $7700.00 | Window Closed / Lapsed |