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US4427437A Expired / Lapsed US ⏱️ 0.0 years remaining

Use of 2-phenoxypyrimidines as herbicides

Assignee: Orica Ltd
•
Filing: 1978-09-05
•
Granted: 1984-01-24
•
Expires: 1998-09-05
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Abstract

Abstract A process of inhibiting the growth of, severely damaging, or killing plants which process comprises applying to the plant or to the growth medium thereof an effective amount of a composition comprising as active ingredient a compound of formula I: ##STR1## wherein A, B and D are independently chosen from the group consisting of hydrogen, halogen, hydroxy, nitro, cyano, thiocyano, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted alkylthio, optionally substituted cycloalkyl, optionally substituted amino, optionally substituted phenyl, carboxy, alkoxycarbonyl, optionally substituted carbamoyl, sulfo, alkylsulfonyl and optionally substituted sulfamoyl; R 2 , R 3 , R 4 , R 5 and R 6 are independently chosen from the group consisting of hydrogen, halogen, nitro, cyano, thiocyano, formyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted alkylcarbonyl, optionally substituted amino, optionally substituted phenyl, optionally substituted carbamoyl, sulfo, alkoxysulfonyl, optionally substituted sulfamoyl and the groups YR 1 and ##STR2## wherein Y is oxygen or sulphur and R 1 is chosen from the group consisting of hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted acyl, optionally substituted alkoxycarbonyl, optionally substituted phenyl and the cation of an inorganic or organic base; X is oxygen or sulphur; and B, R 3 and R 5 are not all hydrogen; or a geometrical or optical isomer thereof; or a tautomer thereof; or a salt thereof; and a carrier therefor.

Inventors

  • 👤 Alexander Serban
  • 👤 Keith G. Watson
  • 👤 Richard B. Warner

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 14:18
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/56; A; A01; A01N; A01N43/00; A01N43/48; A01N43/54; A01P; A01P13/00; C07D239/32; C07D239/34; C07D239/38; C07D239/47; C07D239/52

Claims Analysis

Total Claims: 25
Claim 1
Independent Claim 317 words
A process of inhibiting the growth of, severely damaging, or killing plants which process comprises applying to the plant or to the growth medium thereof an effective amount of a composition comprising as active ingredient a compound of formula I: ##STR24## wherein A and D are independently chosen from the group consisting of hydrogen, halogen, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, C 1 to C 6 (alkoxy)carbonyl and NR 7 R 8 wherein R 7 and R 8 are independently chosen from hydrogen and C 1 to C 6 alkyl; B is chosen from the group consisting of halogen, cyano, C 1 to C 6 (alkoxy)carbonyl, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, NR 7 R 8 wherein R 7 and R 8 are independently hydrogen or C 1 to C 6 alkyl, phenyl, halophenyl and nitrophenyl; R 3 and R 5 are independently chosen from the group consisting of hydrogen, halogen, nitro, cyano, C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 2 to C 6 alkenyloxy, C 2 to C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, phenoxy, halophenoxy, benzyloxy and halobenzyloxy, and wherein at least one of R 3 and R 5 is a substituent other than hydrogen; R 2 , R 4 and R 6 are independently chosen from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, benzyl, phenoxy, halophenoxy, benzyloxy and halobenzyloxy; X is oxygen; or an acid addition salt thereof; and a carrier therefor.
Claim 2
Dependent Claim 317 words
A process of inhibiting the growth of, severely damaging, or killing plants which process comprises applying to the plant or to the growth medium thereof an effective amount of a composition comprising as active ingredient a compound of formula I: ##STR24## wherein A and D are independently chosen from the group consisting of hydrogen, halogen, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, C 1 to C 6 (alkoxy)carbonyl and NR 7 R 8 wherein R 7 and R 8 are independently chosen from hydrogen and C 1 to C 6 alkyl; B is chosen from the group consisting of halogen, cyano, C 1 to C 6 (alkoxy)carbonyl, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, NR 7 R 8 wherein R 7 and R 8 are independently hydrogen or C 1 to C 6 alkyl, phenyl, halophenyl and nitrophenyl; R 3 and R 5 are independently chosen from the group consisting of hydrogen, halogen, nitro, cyano, C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 2 to C 6 alkenyloxy, C 2 to C 6 haloalkenyloxy, C 2 to C 6 alkynyloxy, phenoxy, halophenoxy, benzyloxy and halobenzyloxy, and wherein at least one of R 3 and R 5 is a substituent other than hydrogen; R 2 , R 4 and R 6 are independently chosen from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, benzyl, phenoxy, halophenoxy, benzyloxy and halobenzyloxy; X is oxygen; or an acid addition salt thereof; and a carrier therefor.
Claim 3
Dependent Claim 89 words
A process according to claim 1 wherein in the compound of formula I: A and D are both hydrogen; B is selected from the group consisting of fluorine, chlorine, bromine, iodine and methyl; at least one of R 3 and R 5 is chosen from the group consisting of fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, tertiary butyl, trifluoromethyl, methoxy, ethoxy, propoxy, 3-chloropropoxy, 1,1,2,2-tetrafluoroethoxy, allyloxy, 2-chloroallyloxy, 2-propynyloxy, 4-chlorophenoxy, 4-fluorophenoxy, 4-fluorobenzyloxy, 4-chlorobenzyloxy and benzyloxy; and the remaining R 2 to R 6 substituents are chosen from hydrogen, chlorine and methyl.
Claim 4
Dependent Claim 57 words
A process according to claim 1 wherein in the compound of formula I: A, D, R 2 , R 4 , R 5 and R 6 are all hydrogen; B is selected from the group consisting of fluorine, chlorine, bromine and iodine; and R 3 is selected from the group consisting of chlorine, bromine, iodine and trifluoromethyl.
Claim 5
Dependent Claim 47 words
A process according to claim 1 wherein in the compound of formula I: A, D, R 2 , R 4 , R 5 and R 6 are all hydrogen; B is methyl; and R 3 is selected from the group consisting of chlorine, bromine, iodine and trifluoromethyl.
Claim 6
Dependent Claim 63 words
A process according to claim 1 wherein in the compound of formula I: A, D, R 2 , R 4 , R 5 and R 6 are all hydrogen; B is selected from the group consisting of fluorine, chlorine, bromine and iodine; and R 3 is selected from the group consisting of 3-chloropropoxy, 1,1,2,2-tetrafluoroethoxy, allyloxy, 2-chloroallyloxy, 2-propynyloxy, 4-chlorophenoxy, 4-fluorophenoxy, benzyloxy, 4-fluorobenzyloxy and 4-chlorobenzyloxy.
Claim 7
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR25##
Claim 8
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR26##
Claim 9
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR27##
Claim 10
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR28##
Claim 11
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR29##
Claim 12
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR30##
Claim 13
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR31##
Claim 14
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR32##
Claim 15
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR33##
Claim 16
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR34##
Claim 17
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR35##
Claim 18
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR36##
Claim 19
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR37##
Claim 20
Dependent Claim 13 words
A process according to claim 1 wherein the compound has the formula ##STR38##
Claim 21
Dependent Claim 15 words
A process according to claim 1 for selectively controlling the growth of weeds in crops.
Claim 22
Dependent Claim 15 words
A process according to claim 20 wherein the crops are cotton crops or sunflower crops.
Claim 23
Dependent Claim 12 words
A process according to claim 20 wherein the crops are cereal crops.
Claim 24
Dependent Claim 27 words
A process according to claim 1 wherein the compound of formula I is applied at a rate in the range from 0.01 to 10 kilograms per hectare.
Claim 25
Dependent Claim 20 words
A process according to claim 23 wherein the rate is in the range from 0.1 to 5 kilograms per hectare.

References Cited (Backward Citations)

US3126271A Cited
US3427146A Cited
US3974276A Cited
US3969101A Cited
US3897440A Cited
US3947437A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-01-23 1987-07-25 1988-01-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-01-23 1991-07-25 1992-01-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-01-23 1995-07-25 1996-01-24 $7700.00 Window Closed / Lapsed

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