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US4337268A Expired / Lapsed US ⏱️ 0.0 years remaining

Combating fungi with N-oximinoalkyl-anilides

Assignee: Bayer AG
•
Filing: 1980-05-15
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Granted: 1982-06-29
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Expires: 2000-05-15
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Abstract

Abstract N-Oximinoalkyl-anilides of the formula <IMAGE> (I) in which R1 represents hydrogen, alkyl or halogen, R2 represents hydrogen or alkyl, R3 represents hydrogen or alkyl, R4 represents hydrogen or alkyl, R5 represents hydrogen or alkyl, R6 represents hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl or optionally substituted aralkyl and R7 represents furyl, tetrahydrofuryl, thiophenyl, or tetrahydrothiophenyl; isoxazolyl which is optionally substituted in alkyl; alkyl, alkenyl or alkynyl, in each case optionally substituted by cyano or thiocyano; dihalogenoalkyl or cycloalkyl; or the grouping -CH2Az, -CH2-OR8, -CH2-SR8, -OR8, -SR8, -CH2-OSO2R8, -COOR8 or <IMAGE> wherein R8 represents an optionally substituted alkyl, alkenyl, alkynyl or alkoxyalkyl radical and Az represents pyrazol-1-yl, 1,2,4-thiazol-1-yl or imidazol-1-yl, which possess fungicidal activity.

Inventors

  • 👤 Jorg Stetter
  • 👤 Wilhelm Brandes

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 13:03
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A01; A01N; A01N37/00; A01N37/18; A01N37/22; A01N37/36; A01N43/00; A01N43/02; A01N43/04; A01N43/06; A01N43/08; A01N43/48; A01N43/50; A01N43/64; A01N43/647; A01N43/653; A01N53/00; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 288 words
An N-oximinoalkyl-anilide of the formula ##STR196## in which R 1 represents hydrogen, alkyl of up to 4 carbon atoms or halogen, R 2 represents alkyl of up to 4 carbon atoms, R 3 represents hydrogen or alkyl of up to 4 carbon atoms, R 4 represents hydrogen or alkyl of up to 4 carbon atoms, R 5 represents hydrogen or alkyl of up to 4 carbon atoms, R 6 represents hydrogen; alkyl, alkenyl or alkynyl of up to 4 carbon atoms; alkoxyalkyl or alkylthioalkyl of up to 4 carbon atoms in each alkyl moiety; or optionally substituted aralkyl with 6 to 10 carbon atoms in the aryl part and 1 to 2 carbon atoms in the alkyl part wherein the substituents are selected from the group consisting of halogen, straight-chain or branched alkyl of 1 to 4 carbon atoms, halogenoalkyl of 1 to 2 carbon atoms and 1 to 5 halogen atoms, alkoxy of 1 to 2 carbon atoms, alkylthio of 1 to 2 carbon atoms, cyano and nitro, and R 7 represents furyl, tetrahydrofuryl, thiophenyl, or tetrahydrothiophenyl; isoxazolyl which is optionally substituted by alkyl, alkyl, alkenyl, or alkynyl of up to 4 carbon atoms, in each case optionally substituted by cyano or thiocyano; cycloalkyl of 3 to 7 carbon atoms; or the grouping --CH 2 Az, --CH 2 --OR 8 , --CH 2 --SR 8 , --OR 8 , --SR 8 , --CH 2 --OSO 2 R 8 , --COOR 8 or ##STR197## wherein R 8 represents an alkyl, alkenyl or alkynyl radical of up to 4 carbon atoms optionally substituted by halogen, cyano or thiocyano, or an alkoxyalkyl radical of up to 4 carbon atoms in each alkyl moiety; and Az represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl.
Claim 2
Dependent Claim 288 words
An N-oximinoalkyl-anilide of the formula ##STR196## in which R 1 represents hydrogen, alkyl of up to 4 carbon atoms or halogen, R 2 represents alkyl of up to 4 carbon atoms, R 3 represents hydrogen or alkyl of up to 4 carbon atoms, R 4 represents hydrogen or alkyl of up to 4 carbon atoms, R 5 represents hydrogen or alkyl of up to 4 carbon atoms, R 6 represents hydrogen; alkyl, alkenyl or alkynyl of up to 4 carbon atoms; alkoxyalkyl or alkylthioalkyl of up to 4 carbon atoms in each alkyl moiety; or optionally substituted aralkyl with 6 to 10 carbon atoms in the aryl part and 1 to 2 carbon atoms in the alkyl part wherein the substituents are selected from the group consisting of halogen, straight-chain or branched alkyl of 1 to 4 carbon atoms, halogenoalkyl of 1 to 2 carbon atoms and 1 to 5 halogen atoms, alkoxy of 1 to 2 carbon atoms, alkylthio of 1 to 2 carbon atoms, cyano and nitro, and R 7 represents furyl, tetrahydrofuryl, thiophenyl, or tetrahydrothiophenyl; isoxazolyl which is optionally substituted by alkyl, alkyl, alkenyl, or alkynyl of up to 4 carbon atoms, in each case optionally substituted by cyano or thiocyano; cycloalkyl of 3 to 7 carbon atoms; or the grouping --CH 2 Az, --CH 2 --OR 8 , --CH 2 --SR 8 , --OR 8 , --SR 8 , --CH 2 --OSO 2 R 8 , --COOR 8 or ##STR197## wherein R 8 represents an alkyl, alkenyl or alkynyl radical of up to 4 carbon atoms optionally substituted by halogen, cyano or thiocyano, or an alkoxyalkyl radical of up to 4 carbon atoms in each alkyl moiety; and Az represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl.
Claim 3
Dependent Claim 26 words
A compound according to claim 1, in which R 1 represents hydrogen, straight-chain or branched alkyl with 1 to 4 carbon atoms, fluorine, chlorine or bromine,
Claim 4
Dependent Claim 263 words
R 6 represents hydrogen, straight-chain or branched alkyl with 1 to 4 carbon atoms, alkenyl or alkynyl with in either case 2 to 4 carbon atoms, alkoxyalkyl or alkylthioalkyl with in either case 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the alkoxy or alkylthio part, or optionally substituted aralkyl with 6 to 10 carbon atoms in the aryl part and 1 to 2 carbon atoms in the alkyl part, each substituent being selected from halogen, straight-chain or branched alkyl with 1 to 4 carbon atoms, halogenoalkyl with 1 to 2 carbon atoms and 1 to 5 halogen atoms, alkoxy with 1 to 2 carbon atoms, alkylthio with 1 to 2 carbon atoms, cyano and nitro, R 7 represents furyl, tetrahydrofuryl, thiophenyl or tetrahydrothiophenyl; isoxazolyl which is optionally substituted by methyl or ethyl; alkyl with 1 to 4 carbon atoms or alkenyl or alkynyl with in either case 2 to 4 carbon atoms, in each case optionally substituted by cyano or thiocyano; cycloalkyl with 3 to 7 carbon atoms; or the grouping --CH 2 --Az, --CH 2 --OR 8 , --CH 2 --SR 8 , --OR 8 , --SR 8 , --CH 2 --OSO 2 R 8 , --COOR 8 or ##STR198## Az represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl; and R 8 represents alkyl with 1 to 4 carbon atoms or alkenyl or alkynyl with in either case 2 to 4 carbon atoms, in each case optionally substituted by halogen, cyano or thiocyano, or represents alkoxyalkyl with 1 to 4 carbon atoms in each alkyl part.
Claim 5
Dependent Claim 263 words
R 6 represents hydrogen, straight-chain or branched alkyl with 1 to 4 carbon atoms, alkenyl or alkynyl with in either case 2 to 4 carbon atoms, alkoxyalkyl or alkylthioalkyl with in either case 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the alkoxy or alkylthio part, or optionally substituted aralkyl with 6 to 10 carbon atoms in the aryl part and 1 to 2 carbon atoms in the alkyl part, each substituent being selected from halogen, straight-chain or branched alkyl with 1 to 4 carbon atoms, halogenoalkyl with 1 to 2 carbon atoms and 1 to 5 halogen atoms, alkoxy with 1 to 2 carbon atoms, alkylthio with 1 to 2 carbon atoms, cyano and nitro, R 7 represents furyl, tetrahydrofuryl, thiophenyl or tetrahydrothiophenyl; isoxazolyl which is optionally substituted by methyl or ethyl; alkyl with 1 to 4 carbon atoms or alkenyl or alkynyl with in either case 2 to 4 carbon atoms, in each case optionally substituted by cyano or thiocyano; cycloalkyl with 3 to 7 carbon atoms; or the grouping --CH 2 --Az, --CH 2 --OR 8 , --CH 2 --SR 8 , --OR 8 , --SR 8 , --CH 2 --OSO 2 R 8 , --COOR 8 or ##STR198## Az represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl; and R 8 represents alkyl with 1 to 4 carbon atoms or alkenyl or alkynyl with in either case 2 to 4 carbon atoms, in each case optionally substituted by halogen, cyano or thiocyano, or represents alkoxyalkyl with 1 to 4 carbon atoms in each alkyl part.
Claim 6
Dependent Claim 15 words
A compound according to claim 1, wherein such compound is 2,6-dimethyl-N-(1-methoxyimino-prop-2-yl)-N-methoxyacetyl-aniline of the formula ##STR199##
Claim 7
Dependent Claim 15 words
A compound according to claim 1, wherein such compound is 2,6-dimethyl-N-(2-furoyl)-N-(2-hydroxyimino-prop-1-yl)-aniline of the formula ##STR200##
Claim 8
Dependent Claim 15 words
A compound according to claim 1, wherein such compound is 2,6-dimethyl-N-(1-methoxyimino-eth-2-yl)-N-methoxyacetylaniline of the formula ##STR201##
Claim 9
Dependent Claim 15 words
A compound according to claim 1, wherein such compound is 2,6-dimethyl-N-(1-ethoxyimino-prop-2-yl)-N-methoxyacetyl-aniline of the formula ##STR202##
Claim 10
Dependent Claim 15 words
A compound according to claim 1, wherein such compound is 2-chloro-6-methyl-N-(1-methoxyimino-prop-2-yl)-N-methoxyacetyl-aniline of the formula ##STR203##
Claim 11
Dependent Claim 23 words
A fungicidal composition containing as active ingredient a fungicidally effective amount of a compound according to claim 1 in admixture with a diluent.
Claim 12
Dependent Claim 27 words
A method of combating fungi which comprises applying to the fungi, or to a habitat thereof, a fungicidally effective amount of a compound according to claim 1.
Claim 13
Dependent Claim 17 words
The method according to claim 9, in which said compound is 2,6-dimethyl-N-(1-methoxyimino-prop-2-yl)-N-methoxyacetyl-aniline, 2,6-dimethyl-N-(2-furoyl)-N-(2-hydroxyimino-prop-1-yl)-aniline, 2,6-dimethyl-N-(1-methoxyimino-eth-2-yl)-N-methoxyacetyl-aniline, 2,6-dimethyl-N-(1-ethoxyimino-prop-2-yl)-N-methoxyacetyl-aniline or 2-chloro-6-methyl-N-(1-methoxyimino-prop-2-yl)-N-methoxyacetyl-aniline.

References Cited (Backward Citations)

US3852332A Cited
US4093738A Cited
GB2019404A Cited
US4174210A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-06-28 1985-12-28 1986-06-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-06-28 1989-12-28 1990-06-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-06-28 1993-12-28 1994-06-29 $7700.00 Window Closed / Lapsed

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