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US4477276A Expired / Lapsed US ⏱️ 0.0 years remaining

Heterocyclic phenyl ethers and their herbicidal use

Assignee: Hoechst AG
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Filing: 1982-09-22
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Granted: 1984-10-16
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Expires: 2002-09-22
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Abstract

Abstract Compounds of the formula ##STR1## wherein R is halogen, CF 3 , NO 2 , CN, Alkyl or alkoxy, n is 0 to 3 X is O, S, NH or N-Alkyl, Y is O, S, SO, SO 2 , NH or N-Alkyl, R 1 is H or alkyl and Z is carboxy or hydroxymethyl or functional derivatives of these groups, are valuable herbicides and growth regulators.

Inventors

  • 👤 Lothar Willms
  • 👤 Reinhard Handte
  • 👤 Hilmar Mildenberger
  • 👤 Klaus Bauer
  • 👤 Hermann Bieringer
  • 👤 Helmut Burstell

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 15:16
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A01; A01N; A01N43/00; A01N43/90; C07D513/00; C07D513/02; C07D513/04

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 534 words
A 4-phenoxyalkanecarboxylic acid compound of the formula ##STR18## wherein R is halogen, CF 3 , NO 2 , CN, (C 1 -C 4 )-alkayl, or (C 1 -C 4 )-alkoxy, and n is 0 to 3; X is S or O; Y is O, S, SO, SO 2 , NH, or N-(C 1 -C 4 )-alkyl; R 1 is H or (C 1 -C 4 )-alkyl; and ##STR19## wherein R 2 is H, (C 1 -C 12 )-alkyl, (C 1 -C 12 )-alkyl substituted by at least one member selected from the group consisting of up to 6 halogen atoms, OH, CN, SCN, (C 1 -C 6 )-alkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylsulfinyl, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 6 )-alkoxy-(C 2 -C 6 )-alkoxy, halogeno-(C 1 -C 2 )-alkoxy, methoxyethoxyethoxy, (C 1 -C 4 )-alkylamino, di-(C 1 -C 4 )-alkylamino, phenyl, phenoxy, phenyl or phenoxy mono- or disubstituted by halogen, (C 1 -C 4 )-alkyl, COOR 3 , or --CO--R 3 , (C 5 -C 6 )-cycloalkyl, (C 5 -C 6 )-cycloalkyl substituted by halogen or methyl, (C 3 -C 6 )-alkenyl, halogeno-(C 3 -C 6 )-alkenyl, (C 5 -C 6 )-cycloalkenyl, (C 3 -C 4 )-alkinyl, (C 3 -C 4 )-alkinyl mono- or di-substituted by (C 1 -C 6 )-alkyl, phenyl, halogen, (C 1 -C 2 )-alkoxy, phenyl, phenyl mono-, di-, or tri-substituted by (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halogen, NO 2 or CF 3 , a cation equivalent of organic or inorganic base, or --N=C(R 1 )(R 4 ); R 3 is H, (C 1 -C 4 )-alkyl, phenyl-(C 1 -C 2 )-alkyl, phenyl-(C 1 -C 2 )-alkyl mono- or di-substituted by at least one member selected from the group consisting of (C 1 -C 4 )-alkyl and halogen, (C 3 -C 6 )-alkenyl, phenyl, phenyl mono- or di-substituted by at least one member selected from the group consisting of (C 1 -C 4 )-alkyl and halogen; R 4 and R 5 , taken alone, are the same or different and are H, (C 1 -C 6 )-alkyl, hydroxy-(C 1 -C 6 )-alkyl, (C 5 -C 6 )-cycloalkyl, phenyl, or phenyl mono- di-, or tri-substituted by (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halogen, or CF 3 , but R 4 and R 5 are not both phenyl or substituted phenyl, and if R 4 is H or (C 1 -C 4 )-alkyl, the R 5 may be (C 1 -C 4 )-alkoxycarbonyl-(C 1 -C 4 )-alkyl; 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 4 )-alkyl, (C 1 -C 4 )-alkyl mono-, di- or trisubstituted by halogen, cyclopropyl, (C 3 -C 6 )-alkenyl, phenyl, or phenyl mono-substituted by (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halogen, CF 3 , or nitro; and R 10 is (C 1 -C 4 )-alkyl, phenyl, or phenyl mono- or di-substituted by halogen, CF 3 , NO 2 , or (C 1 -C 4 )-alkyl.
Claim 2
Dependent Claim 534 words
A 4-phenoxyalkanecarboxylic acid compound of the formula ##STR18## wherein R is halogen, CF 3 , NO 2 , CN, (C 1 -C 4 )-alkayl, or (C 1 -C 4 )-alkoxy, and n is 0 to 3; X is S or O; Y is O, S, SO, SO 2 , NH, or N-(C 1 -C 4 )-alkyl; R 1 is H or (C 1 -C 4 )-alkyl; and ##STR19## wherein R 2 is H, (C 1 -C 12 )-alkyl, (C 1 -C 12 )-alkyl substituted by at least one member selected from the group consisting of up to 6 halogen atoms, OH, CN, SCN, (C 1 -C 6 )-alkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylsulfinyl, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 6 )-alkoxy-(C 2 -C 6 )-alkoxy, halogeno-(C 1 -C 2 )-alkoxy, methoxyethoxyethoxy, (C 1 -C 4 )-alkylamino, di-(C 1 -C 4 )-alkylamino, phenyl, phenoxy, phenyl or phenoxy mono- or disubstituted by halogen, (C 1 -C 4 )-alkyl, COOR 3 , or --CO--R 3 , (C 5 -C 6 )-cycloalkyl, (C 5 -C 6 )-cycloalkyl substituted by halogen or methyl, (C 3 -C 6 )-alkenyl, halogeno-(C 3 -C 6 )-alkenyl, (C 5 -C 6 )-cycloalkenyl, (C 3 -C 4 )-alkinyl, (C 3 -C 4 )-alkinyl mono- or di-substituted by (C 1 -C 6 )-alkyl, phenyl, halogen, (C 1 -C 2 )-alkoxy, phenyl, phenyl mono-, di-, or tri-substituted by (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halogen, NO 2 or CF 3 , a cation equivalent of organic or inorganic base, or --N=C(R 1 )(R 4 ); R 3 is H, (C 1 -C 4 )-alkyl, phenyl-(C 1 -C 2 )-alkyl, phenyl-(C 1 -C 2 )-alkyl mono- or di-substituted by at least one member selected from the group consisting of (C 1 -C 4 )-alkyl and halogen, (C 3 -C 6 )-alkenyl, phenyl, phenyl mono- or di-substituted by at least one member selected from the group consisting of (C 1 -C 4 )-alkyl and halogen; R 4 and R 5 , taken alone, are the same or different and are H, (C 1 -C 6 )-alkyl, hydroxy-(C 1 -C 6 )-alkyl, (C 5 -C 6 )-cycloalkyl, phenyl, or phenyl mono- di-, or tri-substituted by (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halogen, or CF 3 , but R 4 and R 5 are not both phenyl or substituted phenyl, and if R 4 is H or (C 1 -C 4 )-alkyl, the R 5 may be (C 1 -C 4 )-alkoxycarbonyl-(C 1 -C 4 )-alkyl; 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 4 )-alkyl, (C 1 -C 4 )-alkyl mono-, di- or trisubstituted by halogen, cyclopropyl, (C 3 -C 6 )-alkenyl, phenyl, or phenyl mono-substituted by (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halogen, CF 3 , or nitro; and R 10 is (C 1 -C 4 )-alkyl, phenyl, or phenyl mono- or di-substituted by halogen, CF 3 , NO 2 , or (C 1 -C 4 )-alkyl.
Claim 3
Dependent Claim 36 words
A compound as in claim 1 wherein R is hydrogen (n=0) or chlorine in the 5-position (n=1), Y is oxygen, R 1 is CH 3 , and Z is --COOH or --COO--(C 1 -C 4 )-alkyl.
Claim 4
Dependent Claim 9 words
A compound as in claim 1 which is ##STR20##
Claim 5
Dependent Claim 9 words
A compound as in claim 1 which is ##STR21##
Claim 6
Dependent Claim 9 words
A compound as in claim 1 which is ##STR22##
Claim 7
Dependent Claim 20 words
A herbicidal composition which comprises a herbicidally effective amount of a compound as in claim 1 and a carrier therefor.
Claim 8
Dependent Claim 25 words
A growth regulating composition which comprises a compound as in claim 1 in an amount which is effective to regulate growth and a carrier therefor.
Claim 9
Dependent Claim 33 words
A method for combatting undesirable plant growth which comprises applying a herbicidally effective amount of a compound as in claim 1 to the undesirable plants or to the area on which they grow.
Claim 10
Dependent Claim 28 words
A method for regulating the growth of useful plants which comprises applying to said plants a compound as in claim 1 in an amount effective to regulate growth.

References Cited (Backward Citations)

US4130413A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-10-16 1988-04-16 1988-10-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-10-16 1992-04-16 1992-10-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-10-16 1996-04-16 1996-10-16 $7700.00 Window Closed / Lapsed

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