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US 5,300,477 AGranted
2-arylpyrimidines and herbicidal use thereof
AssigneeRohm and Haas Company
InventorColin M. Tice
Life of this patent
Estimating the term…
Abstract
A class of 2-arylpyrimidines which is useful in the control of weeds is of the general formula: ##STR1## wherein R.sup.2 is an optionally substituted aromatic ring; R.sup.3 is a saturated or unsaturated alkyl group; R.sup.5 is selected from hydrogen, halo, alkyl, alkenyl, alkynyl, alkoxy, and alkylthio; R.sup.6 is selected from hydrogen, halo, alkyl, haloalkyl, aryl, and alkoxy; and X is oxygen or sulfur.
Claims13
A compound of the formula:
- ##STR7## wherein (a) R.sup.2 is a furyl, phenyl, naphthyl, pyridyl, or thienyl group,
- each of said group is optionally substituted with up to three substituents independently selected from a bromo, chloro, fluoro, (C.sub.1 -C.sub.12)alkyl, cyclo(C.sub.3 -C.sub.8)alkyl, (C.sub.2 -C.sub.12)alkenyl, cyclo(C.sub.3 -C.sub.8)alkenyl, (C.sub.2 -C.sub.12)alkynyl, halo(C.sub.1 -C.sub.12)alkyl, polyhalo(C.sub.1 -C.sub.12)alkyl, halo(C.sub.2 -C.sub.12)alkenyl, polyhalo(C.sub.2 -C.sub.12)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl, (C.sub.1 -C.sub.12)alkoxy, (C.sub.1 -C.sub.12)alkylthio, (C.sub.1 -C.sub.12)alkylsulfonyl, (C.sub.1 -C.sub.12)alkylsulfinyl, phenyl, phen(C.sub.1 -C.sub.12)alkyl, phen(C.sub.2 -C.sub.12)alkenyl, phen(C.sub.2 -C.sub.12)alkynyl, cyano, halo(C.sub.1 -C.sub.12)alkoxy, 1,3-dioxolan-2-yl, hydroxyimino, or nitro group;
- and when R.sup.2 is pyridyl, such pyridyl group is optionally substituted with oxygen on the nitrogen of the pyridyl group;
- or R.sup.2 is a furyl, phenyl, naphthyl, pyridyl or thienyl group having a fused ring moiety composed of an oxymethyleneoxy or an oxoethyleneoxy link bonds to adjacent carbon atoms or said group;
- (b) R.sup.3 is a (C.sub.1 -C.sub.3)alkyl, halo(C.sub.1 -C.sub.3)alkyl, polyhalo(C.sub.1 -C.sub.3)alkyl, (C.sub.3 -C.sub.4)alkenyl, (C.sub.5 -C.sub.6)alkenynyl, (C.sub.3 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl, di(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl, or 2-oxo(C.sub.2 -C.sub.3)alkyl, trimethylsilyl(C.sub.3 -C.sub.4)alkynyl or cyano(C.sub.1 -C.sub.6)alkyl group, each of said (C.sub.3 -C.sub.4)alkenyl, or (C.sub.3 -C.sub.6)alkynyl group is optionally substituted with up to five halogens;
- and
- (c) R.sup.5 is a hydrogen, (C.sub.1 -C.sub.5)alkyl, (C.sub.3 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, halo(C.sub.1 -C.sub.6)alkyl, polyhalo(C.sub.1 -C.sub.6)alkyl, halo(C.sub.2 -C.sub.6)alkenyl, polyhalo(C.sub.2 -C.sub.6)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl, halo(C.sub.1 -C.sub.6)alkoxy, polyhalo(C.sub.1 -C.sub.6)alkoxy, trimethylsilyl(C.sub.2 -C.sub.3)alkynyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1 -C.sub.3)alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl, halo, or cyano group;
- and
- (d) R.sup.6 is a hydrogen, halo, (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, halo(C.sub.1 -C.sub.6)alkyl, polyhalo(C.sub.1 -C.sub.6)alkyl, halo(C.sub.2 -C.sub.6)alkenyl, polyhalo(C.sub.2 -C.sub.6)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1 -C.sub.3)alkoxycarbonyl, (C.sub.1 -C.sub.3)alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl, (C.sub.6 -C.sub.10)aryl, ar(C.sub.1 -C.sub.4)alkyl, cyclo(C.sub.3 -C.sub.7)alkyl, (C.sub.4 -C.sub.5)heterocyclyl selected from a group consisting of furyl, pyridyl and thienyl, (C.sub.1 -C.sub.3)alkylamino, di(C.sub.1 -C.sub.3)alkylamino, di(C.sub.1 -C.sub.3)alkylaminocarbonyl, halo(C.sub.1 -C.sub.6)alkylthio, polyhalo(C.sub.1 -C.sub.6)alkythio, halo(C.sub.1 -C.sub.6)alkoxy, polyhalo(C.sub.1 -C.sub.6)alkoxy, (C.sub.6 -C.sub.10)aryloxy or cyano group;
- said (C.sub.6 -C.sub.10)aryl, ar(C.sub.1 -C.sub.4 )alkyl and (C.sub.6 -C.sub.10)aryloxy groups being optionally substituted with up to three substituents independently selected from bromo;
- chloro;
- fluoro;
- (C.sub.1 -C.sub.12)alkyl, cyclo(C.sub.3 -C.sub.8)alkyl, (C.sub.2 -C.sub.12)alkenyl, cyclo(C.sub.3 -C.sub.8)alkenyl, (C.sub.2 -C.sub.12)alkynyl, halo(C.sub.1 -C.sub.12)alkyl, polyhalo(C.sub.1 -C.sub.12)alkyl, halo(C.sub.2 -C.sub.12)alkenyl, polyhalo(C.sub.2 -C.sub.12)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl;
- (C.sub.1 -C.sub.12)alkoxy, (C.sub.1 -C.sub.12)alkylthio, (C.sub.1 -.sub.12)alkylsulfonyl, (C.sub.1 -C.sub.12)alkylsulfinyl, phenyl, phen(C.sub.1 -C.sub.12)alkyl, phen(C.sub.2 -C.sub.12)alkenyl, phen(C.sub.2 -C.sub.12)alkynyl, cyano, halo(C.sub.1 -C.sub.12)alkoxy, 1,3-dioxalan-2-yl, hydroxyimino, and nitro;
- and
- (e) X is oxygen or sulfur;
- provided that
- (1) when R.sup.2 and R.sup.6 are phenyl, then R.sup.5 is neither alkyl nor cyano;
- (2) when R.sup.2 is phenyl, then R.sup.6 is neither alkyl nor haloalkyl;
- and
- (3) when X is sulfur and R.sup.2 is phenyl, then R.sup.3 is not alkyl.
18 more elements
A compound of the formula:
- ##STR8## wherein (a) R.sup.2 is a phenyl, pyridyl, or thienyl group,
- each of said group is optionally substituted with up to three substituents independently selected from a bromo, chloro, fluoro, (C.sub.1 -C.sub.12)alkyl, cyclo(C.sub.3 -C.sub.8)alkyl, (C.sub.2 -C.sub.12)alkenyl, cyclo(C.sub.3 -C.sub.8)alkenyl, (C.sub.2 -C.sub.12)alkynyl, halo(C.sub.1 -C.sub.12)alkyl, polyhalo(C.sub.1 -C.sub.12)alkyl, halo(C.sub.2 -C.sub.12)alkenyl, polyhalo(C.sub.2 -C.sub.12)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl, (C.sub.1 -C.sub.12)alkoxy, (C.sub.1 -C.sub.12)alkylthio, (C.sub.1 -C.sub.12)alkylsulfonyl, (C.sub.1 -C.sub.12)alkylsulfinyl, phenyl, phen(C.sub.1 -C.sub.12)alkyl, phen(C.sub.2 -C.sub.12)alkenyl, phen(C.sub.2 -C.sub.12)alkynyl, cyano, halo(C.sub.1 -C.sub.12)alkoxy, 1,3-dioxolan-2-yl, hydroxyimino, or nitro group;
- and when R.sup.2 is pyridyl, such pyridyl group is optionally substituted with oxygen on the nitrogen of the pyridyl group;
- (b) R.sup.3 is a (C.sub.3 -C.sub.6)alkynyl group optionally substituted with up to five halogens;
- and
- (c) R.sup.5 is a hydrogen, (C.sub.1 -C.sub.5)alkyl, (C.sub.3 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, halo(C.sub.1 -C.sub.6)alkyl, polyhalo(C.sub.1 -C.sub.6)alkyl, halo(C.sub.2 -C.sub.6)alkenyl, polyhalo(C.sub.2 -C.sub.6)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl, halo(C.sub.1 -C.sub.6)alkoxy, polyhalo(C.sub.1 -C.sub.6)alkoxy, trimethylsilyl(C.sub.2 -C.sub.3)alkynyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1 -C.sub.3)alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl, halo, or cyano group;
- and
- (d) R.sup.6 is a hydrogen, halo, (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, halo(C.sub.1 -C.sub.6)alkyl, polyhalo(C.sub.1 -C.sub.6)alkyl, halo(C.sub.2 -C.sub.6)alkenyl, polyhalo(C.sub.2 -C.sub.6)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1 -C.sub.3)alkoxycarbonyl, (C.sub.1 -C.sub.3)alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl, (C.sub.6 -C.sub.10)aryl, ar(C.sub.1 -C.sub.4)alkyl, cyclo(C.sub.3 -C.sub.7)alkyl, (C.sub.4 -C.sub.5)heterocyclyl selected from a group consisting of furyl, pyridyl and thienyl, (C.sub.1 -C.sub.3)alkylamino, di(C.sub.1 -C.sub.3)alkylamino, di(C.sub.1 -C.sub.3)alkylaminocarbonyl, halo(C.sub.1 -C.sub.6)alkylthio, polyhalo(C.sub.1 -C.sub.6)alkythio, halo(C.sub.1 -C.sub.6)alkoxy, polyhalo(C.sub.1 -C.sub.6)alkoxy, (C.sub.6 -C.sub.10)aryloxy or cyano group;
- said (C.sub.6 -C.sub.10)aryl, ar(C.sub.1 -C.sub.4 )alkyl and (C.sub.6 -C.sub.10)aryloxy groups being optionally substituted with up to three substituents independently selected from bromo;
- chloro;
- fluoro;
- (C.sub.1 -C.sub.12)alkyl, cyclo(C.sub.3 -C.sub.8)alkyl, (C.sub.2 -C.sub.12)alkenyl, cyclo(C.sub.3 -C.sub.8)alkenyl, (C.sub.2 -C.sub.12)alkynyl, halo(C.sub.1 -C.sub.12)alkyl, polyhalo(C.sub.1 -C.sub.12)alkyl, halo(C.sub.2 -C.sub.12)alkenyl, polyhalo(C.sub.2 -C.sub.12)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl;
- (C.sub.1 -C.sub.12)alkoxy, (C.sub.1 -C.sub.12)alkylthio, (C.sub.1 -C.sub.12)alkylsulfonyl, (C.sub.1 -C.sub.12)alkylsulfinyl, phenyl, phen(C.sub.1 -C.sub.12)alkyl, phen(C.sub.2 -C.sub.12)alkenyl, phen(C.sub.2 -C.sub.12)alkynyl, cyano, halo(C.sub.1 -C.sub.12)alkoxy, 1,3-dioxalan-2-yl, hydroxyimino, and nitro;
- and
- (e) X is oxygen or sulfur.
12 more elements
A herbicidal composition comprising a herbicidally effective amount of a compound of the formula:
- ##STR9## wherein (a) R.sup.2 is a furyl, phenyl, naphthyl, pyridyl, or thienyl group,
- each of said group is optionally substituted with up to three substituents independently selected from a bromo, chloro, fluoro, (C.sub.1 -C.sub.12)alkyl, cyclo(C.sub.3 -C.sub.8)alkyl, (C.sub.2 -C.sub.12)alkenyl, cyclo(C.sub.3 -C.sub.8)alkenyl, (C.sub.2 -C.sub.12)alkynyl, halo(C.sub.1 -C.sub.12)alkyl, polyhalo(C.sub.1 -C.sub.12)alkyl, halo(C.sub.2 -C.sub.12)alkenyl, polyhalo(C.sub.2 -C.sub.12)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl, (C.sub.1 -C.sub.12)alkoxy, (C.sub.1 -C.sub.12)alkylthio, (C.sub.1 -C.sub.12)alkylsulfonyl, (C.sub.1 -C.sub.12)alkylsulfinyl, phenyl, phen(C.sub.1 -C.sub.12)alkyl, phen(C.sub.2 -C.sub.12)alkenyl, phen(C.sub.2 -C.sub.12)alkynyl, cyano, halo(C.sub.1 -C.sub.12)alkoxy, 1,3-dioxolan-2-yl, hydroxyimino, or nitro group;
- and when R.sup.2 is pyridyl, such pyridyl group is optionally substituted with oxygen on the nitrogen of the pyridyl group;
- or R.sup.2 is a furyl, phenyl, naphthyl, pyridyl or thienyl group having a fused ring moiety composed of an oxymethyleneoxy or an oxoethyleneoxy link bonds to adjacent carbon atoms or said group;
- (b) R.sup.3 is a (C.sub.1 -C.sub.3)alkyl, (C.sub.3 -C.sub.4)alkenyl, (C.sub.5 -C.sub.6)alkenynyl, (C.sub.3 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl, di(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl, (halo(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.6)alkyl, 2-oxo(C.sub.2 -C.sub.3)alkyl, trimethylsilyl(C.sub.3 -C.sub.4)alkynyl, cyano(C.sub.1 -C.sub.6)alkyl, or phenyl group, each of said (C.sub.1 -C.sub.3)alkyl, (C.sub.3 -C.sub.4)alkenyl, or (C.sub.3 -C.sub.6)alkynyl group is optionally substituted with up to five halogens;
- and
- (c) R.sup.5 is a hydrogen, (C.sub.1 -C.sub.5)alkyl, (C.sub.3 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, halo(C.sub.1 -C.sub.6)alkyl, polyhalo(C.sub.1 -C.sub.6)alkyl, halo(C.sub.2 -C.sub.6)alkenyl, polyhalo(C.sub.2 -C.sub.6)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl, trimethylsilyl(C.sub.2 -C.sub.3)alkynyl, (C.sub.1 -C.sub.6)alkoxy, halo(C.sub.1 -C.sub.6)alkoxy, polyhalo(C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1 -C.sub.3)alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl, halo, or cyano group;
- and
- (d) R.sup.6 is a hydrogen, halo (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.6)alkenyl, (C.sub.2 -C.sub.6)alkynyl, halo(C.sub.1 -C.sub.6)alkyl, polyhalo(C.sub.1 -C.sub.6)alkyl, halo(C.sub.2 -C.sub.6)alkenyl, polyhalo(C.sub.2 -C.sub.6)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1 -C.sub.3)alkoxycarbonyl, (C.sub.1 -C.sub.3)alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl, (C.sub.6 -C.sub.10)aryl, ar(C.sub.1 -C.sub.4)alkyl, cyclo(C.sub.3 -C.sub.7)alkyl, (C.sub.4 -C.sub.5)heterocyclyl selected from a group consisting of furyl, thienyl or pyridyl, (C.sub.1 -C.sub.3)alkylamino, di(C.sub.1 -C.sub.3)alkylamino, di(C.sub.1 -C.sub.3)alkylaminocarbonyl, halo(C.sub.1 -C.sub.6)alkylthio, polyhalo(C.sub.1 -C.sub.6)alkythio, halo(C.sub.1 -C.sub.6)alkoxy, polyhalo(C.sub.1 -C.sub.6)alkoxy, (C.sub.6 -C.sub.10)aryloxy or cyano group;
- said (C.sub.6 -C.sub.10)aryl, ar(C.sub.1 -C.sub.4)alkyl and (C.sub.6 - C.sub.10)aryloxy groups being optionally substituted with up to three substituents independently selected from bromo;
- chloro;
- fluoro;
- (C.sub.1 -C.sub.12)alkyl, cyclo(C.sub.3 -C.sub.8)alkyl, (C.sub.2 -C.sub.12)alkenyl, cyclo(C.sub.3 -C.sub.8)alkenyl, (C.sub.2 -C.sub.12)alkynyl, halo(C.sub.1 -C.sub.12)alkyl, polyhalo(C.sub.1 -C.sub.12)alkyl, halo(C.sub.2 -C.sub.12)alkenyl, polyhalo(C.sub.2 -C.sub.12)alkenyl, halo(C.sub.2 -C.sub.6)alkynyl, polyhalo(C.sub.2 -C.sub.6)alkynyl;
- (C.sub.1 -C.sub.12)alkoxy, (C.sub.1 -C.sub.12)alkylthio, (C.sub.1 -C.sub.12)alkylsulfonyl, (C.sub.1 -C.sub.12)alkylsulfinyl, phenyl, phen(C.sub.1 -C.sub.12)alkyl, phen(C.sub.2 -C.sub.12)alkenyl, phen(C.sub.2 -C.sub.12)alkynyl, cyano, halo(C.sub.1 -C.sub.12)alkoxy, 1,3-dioxalan-2-yl, hydroxyimino, and nitro;
- and
- (e) X is oxygen or sulfur.
13 more elements
Dependencies are inferred from the claim text.