6-arylpyrimidines and herbicidal use
First Claim
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1. A compound of the formula ##STR10## wherein (a) R2 is a hydrogen, straight (C1 -C6)alkyl, branched (C3 -C8)alkyl, (C2 -C6)alkenyl, (C2 -C6)alkynyl, halo(C1 -C6)alkyl, polyhalo(C1 -C6)alkyl, halo(C2 -C6)alkenyl, polyhalo(C2 -C6)alkenyl, halo(C2 -C6)alkynyl, polyhalo(C2 -C6)alkynyl, (C1 -C4)alkoxy(C1 -C4)alkyl, (C1 -C6)alkylthio, (C1 -C6)alkoxy, (C1 -C3)alkoxycarbonyl, (C1 -C3)alkoxycarbonyl(C1 -C3)alkyl, ar(C1 -C4)alkyl, cyclo(C3 -C7)alkyl, (C1 -C3)alkylamino, di(C1 -C3)alkylamino, di(C1 -C3)alkylaminocaryl, halo or cyano group;
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(c) R5 is a (C1 -C4)alkyl;
(C2 -C6)alkenyl;
or (C2 -C6)alkynyl group;
or (C5 -C6)alkenylnyl group, or (C1 -C4)alkoxy(C1 -C4)alkyl group;
provided that when R6 is phenyl or substituted phenyl, then R5 is not (C1 -C4)alkyl; and
(d) R6 is a furyl, phenyl, pyridyl, or thienyl group, each of said group is optionally substituted with up to three substituents independently selected from bromo;
chloro;
fluoro;
(C1 -C12)alkyl, cyclo(C3 -C8)alkyl, (C2 -C12)alkenyl, cyclo(C3 -C8)alkenyl, (C2 -C12)alkynyl, halo(C1 -C12)alkyl, polyhalo(C1 -C12)alkyl, halo(C2 -C12)alkenyl, polyhalo(C2 -C12)alkenyl, halo(C2 -C6)alkynyl;
polyhalo(C2 -C6)alkynyl;
(C1 -C12)alkylthio, (C1 -C12)alkylsulfonyl;
(C1 -C12)alkylsulfinyl;
phenyl;
phen(C1 -C12)alkyl;
phen(C2 -C12)alkenyl;
phen(C2-C12)alkynyl;
cyano;
halo(C1 -C6)alkoxy, carbo(C1 -C6)alkoxy, and nitro group; and
(e) X is oxygen or sulfur.
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Abstract
A class of 6-arylpyrimidines which is useful in the control of weeds is of the general formulae: ##STR1## wherein R2 is selected from hydrogen, halo, substituted or unsubstituted alkyl, haloalkyl, polyhaloalkyl, haloalkenyl, polyhaloalkenyl, haloalkynyl, polyhaloalkynyl, alkenyl, alkynyl, alkoxy, alkylthio, alkoxycarbonylalkyl, cyano, alkoxyalkyl, alkoxycarbonyl, cycloalkyl, aralkyl, alkylamino, dialkylamino, or dialkylaminocarbonyl group; R3 is an alkyl, alkenyl, alkynyl, or haloalkyl group; R5 is an alkyl, alkenyl, alkynyl, alkenynyl, or alkoxyalkyl, group; R6 is an aryl group (e.g. aromatic ring); and X is oxygen or sulfur. R2 and R3 may form a fused ring.
12 Citations
9 Claims
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1. A compound of the formula ##STR10## wherein (a) R2 is a hydrogen, straight (C1 -C6)alkyl, branched (C3 -C8)alkyl, (C2 -C6)alkenyl, (C2 -C6)alkynyl, halo(C1 -C6)alkyl, polyhalo(C1 -C6)alkyl, halo(C2 -C6)alkenyl, polyhalo(C2 -C6)alkenyl, halo(C2 -C6)alkynyl, polyhalo(C2 -C6)alkynyl, (C1 -C4)alkoxy(C1 -C4)alkyl, (C1 -C6)alkylthio, (C1 -C6)alkoxy, (C1 -C3)alkoxycarbonyl, (C1 -C3)alkoxycarbonyl(C1 -C3)alkyl, ar(C1 -C4)alkyl, cyclo(C3 -C7)alkyl, (C1 -C3)alkylamino, di(C1 -C3)alkylamino, di(C1 -C3)alkylaminocaryl, halo or cyano group;
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(b) R3 is a (C1 -C4)alkyl, (C3 -C6)alkenyl, (C3 -C6)alkynyl, halo- or polyhalo(C1 -C6)alkyl group; and (c) R5 is a (C1 -C4)alkyl;
(C2 -C6)alkenyl;
or (C2 -C6)alkynyl group;
or (C5 -C6)alkenylnyl group, or (C1 -C4)alkoxy(C1 -C4)alkyl group;
provided that when R6 is phenyl or substituted phenyl, then R5 is not (C1 -C4)alkyl; and(d) R6 is a furyl, phenyl, pyridyl, or thienyl group, each of said group is optionally substituted with up to three substituents independently selected from bromo;
chloro;
fluoro;
(C1 -C12)alkyl, cyclo(C3 -C8)alkyl, (C2 -C12)alkenyl, cyclo(C3 -C8)alkenyl, (C2 -C12)alkynyl, halo(C1 -C12)alkyl, polyhalo(C1 -C12)alkyl, halo(C2 -C12)alkenyl, polyhalo(C2 -C12)alkenyl, halo(C2 -C6)alkynyl;
polyhalo(C2 -C6)alkynyl;
(C1 -C12)alkylthio, (C1 -C12)alkylsulfonyl;
(C1 -C12)alkylsulfinyl;
phenyl;
phen(C1 -C12)alkyl;
phen(C2 -C12)alkenyl;
phen(C2-C12)alkynyl;
cyano;
halo(C1 -C6)alkoxy, carbo(C1 -C6)alkoxy, and nitro group; and(e) X is oxygen or sulfur. - View Dependent Claims (2, 3, 4, 5, 6, 7)
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8. A method of controlling a weed comprising applying to said weed or to the locus of said weed or to the growth medium of said weed a herbicidally effective amount of a compound of the formula:
- ##STR11## wherein (a) R2 is a hydrogen, straight (C1 -C6)alkyl, branched (C3 -C8)alkyl, (C2 -C6)alkenyl, (C2 -C6)alkynyl, halo(C1 -C6)alkyl, polyhalo(C1 -C6)alkyl, halo(C2 -C6)alkenyl, polyhalo(C2 -C6)alkenyl, halo(C2 -C6)alkynyl, polyhalo(C2 -C6)alkynyl, (C1 -C4)alkoxy(C1 -C4)alkyl, (C1 -C6)alkylthio, (C1 -C6)alkoxy, (C1 -C3)alkoxycarbonyl, (C1 -C3)alkoxycarbonyl(C1 -C3)alkyl, ar(C1 -C4)alkyl, cyclo(C3 -C7)alkyl, (C1 -C3)alkylamino, di(C1 -C3)alkylamino, di(C1 -C3)alkylaminocarbonyl, halo or cyano group; and
(b) R3 is a (C1 -C4)alkyl, (C3 -C6)alkenyl, (C3 -C6)alkynyl, halo- or polyhalo(C1 -C6)alkyl group; and (c) R5 is a (C1 -C4)alkyl;
(C2 -C6)alkenyl;
or (C2 -C6)alkynyl group;
or (C5-C6)alkenynyl group, or (C1 -C4)alkoxy(C1 -C4)alkyl group; and(d) R6 is a furyl, phenyl, pyridyl, or thienyl group, each of said group is optionally substituted with up to three substituents independently selected from bromo;
chloro;
fluoro;
(C1 -C12)alkyl, cyclo(C3 -C8)alkyl, (C2 -C12)alkenyl, cyclo(C3 -C8)alkenyl, (C2 -C12)alkynyl, halo(C1 -C12)alkyl, polyhalo(C1 -C12)alkyl, halo(C2 -C12)alkenyl, polyhalo(C2 -C12)alkenyl, halo(C2 -C6)alkynyl;
polyhalo(C2 -C6)alkynyl;
(C1 -C12)alkoxy, (C1 -C12)alkylthio, (C1 -C12)alkylsulfonyl;
(C1 -C12)alkylsulfinyl;
phenyl;
phen(C1 -C12)alkyl;
phen(C2 -C12)alkenyl;
phen(C2 -C12)alkynyl;
cyano;
halo(C1 -C6)alkoxy;
carbo(C1 -C6)alkoxy; and
nitro group; and(e) X is oxygen or sulfur.
- ##STR11## wherein (a) R2 is a hydrogen, straight (C1 -C6)alkyl, branched (C3 -C8)alkyl, (C2 -C6)alkenyl, (C2 -C6)alkynyl, halo(C1 -C6)alkyl, polyhalo(C1 -C6)alkyl, halo(C2 -C6)alkenyl, polyhalo(C2 -C6)alkenyl, halo(C2 -C6)alkynyl, polyhalo(C2 -C6)alkynyl, (C1 -C4)alkoxy(C1 -C4)alkyl, (C1 -C6)alkylthio, (C1 -C6)alkoxy, (C1 -C3)alkoxycarbonyl, (C1 -C3)alkoxycarbonyl(C1 -C3)alkyl, ar(C1 -C4)alkyl, cyclo(C3 -C7)alkyl, (C1 -C3)alkylamino, di(C1 -C3)alkylamino, di(C1 -C3)alkylaminocarbonyl, halo or cyano group; and
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9. A composition comprising a carrier and a herbicidally effect amount of a compound of the formula:
- ##STR12## wherein (a) R2 is a hydrogen, straight (C1 -C6)alkyl, branched (C3 -C8)alkyl, (C2 -C6)alkenyl, (C2 -C6)alkynyl, halo(C1 -C6)alkyl, polyhalo(C1 -C6)alkyl, halo(C2 -C6)alkenyl, polyhalo(C2 -C6)alkenyl, halo(C2 -C6)alkynyl, polyhalo(C2 -C6)alkynyl, (C1 -C4)alkoxy(C1 -C4)alkyl, (C1 -C6)alkylthio, (C1 -C6)alkoxy, (C1 -C3)alkoxycarbonyl, (C1 -C3)alkoxycarbonyl(C1 -C3)alkyl, ar(C1 -C4)alkyl, cyclo(C3 -C7)alkyl, (C1 -C3)alkylamino, di(C1 -C3)alkylamino, di(C1 -C3)alkylaminocarbonyl, halo or cyano group; and
(b) R3 is a (C1 -C4)alkyl, (C3 -C6)alkenyl, (C3 -C6)alkynyl, halo- or polyhalo(C1 -C6)alkyl group; and (c) R5 is a (C1 -C4)alkyl;
(C2 -C6)alkenyl;
or (C2 -C6)alkynyl group;
or (C5 -C6)alkenynyl group, or (C1 -C4)alkoxy(C1 -C4)alkyl group; and(d) R6 is a furyl, phenyl, pyridyl, or thienyl group, each of said group is optionally substituted with up to three substituents independently selected from bromo;
chloro;
fluoro;
(C1 -C12)alkyl, cyclo(C3 -C8)alkyl, (C2 -C12)alkenyl, cyclo(C3 -C8)alkenyl, (C2 -C12)alkynyl, halo(C1 -C12)alkyl, polyhalo(C1 -C12)alkyl, halo(C2 -C12)alkenyl, polyhalo(C2 -C12)alkenyl, halo(C2 -C6)alkynyl;
polyhalo(C2 -C6)alkynyl;
(C1 -C12)alkoxy, (C1 -C12)alkylthio, (C1 -C12)alkylsulfonyl;
(C1 -C12)alkylsulfinyl;
phenyl;
phen(C1 -C12)alkyl;
phen(C2 -C12)alkenyl;
phen(C2 -C12)alkynyl;
cyano;
halo(C1 -C6)alkoxy;
carbo(C1 -C6)alkoxy; and
nitro group; and(e) X is oxygen or sulfur.
- ##STR12## wherein (a) R2 is a hydrogen, straight (C1 -C6)alkyl, branched (C3 -C8)alkyl, (C2 -C6)alkenyl, (C2 -C6)alkynyl, halo(C1 -C6)alkyl, polyhalo(C1 -C6)alkyl, halo(C2 -C6)alkenyl, polyhalo(C2 -C6)alkenyl, halo(C2 -C6)alkynyl, polyhalo(C2 -C6)alkynyl, (C1 -C4)alkoxy(C1 -C4)alkyl, (C1 -C6)alkylthio, (C1 -C6)alkoxy, (C1 -C3)alkoxycarbonyl, (C1 -C3)alkoxycarbonyl(C1 -C3)alkyl, ar(C1 -C4)alkyl, cyclo(C3 -C7)alkyl, (C1 -C3)alkylamino, di(C1 -C3)alkylamino, di(C1 -C3)alkylaminocarbonyl, halo or cyano group; and
Specification
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Current AssigneeRohm and Haas Company (Dow, Inc.)
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Original AssigneeRohm and Haas Company (Dow, Inc.)
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InventorsTice, Colin M.
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Primary Examiner(s)Ford, John M.
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Application NumberUS07/916,315Time in Patent Office620 DaysField of Search71/92, 544/309, 544/310, 544/311, 544/312, 544/314, 544/319, 544/320, 544/321, 544/330, 544/331, 544/332, 504/242, 504/243US Class Current504/242CPC Class CodesA01N 43/54 1,3-Diazines; Hydrogenated ...A01N 43/90 having two or more relevant...C07D 239/36 as doubly bound oxygen atom...C07D 471/04 Ortho-condensed systems
