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US 4,692,184 AGranted
2,6-substituted pyridine compounds
AssigneeMonsanto Company
InventorLen F. Lee
Life of this patent
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Abstract
There are disclosed novel 2,6-substituted-3,5-pyridinedicarboxylic acids, esters, salts, amides, halides, and cyano compounds useful as herbicides, and as intermediates which provide herbicides.
Claims34
A compound represented by the structural formula ##STR48## wherein:
- R is selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, lower alkenylalkyl, haloalkyl, haloalkenyl, C.sub.3-7 cycloalkyl, C.sub.3-6 cycloalkanylalkyl, phenyl, alkoxyalkyl, benzyloxymethyl, alkylthioalkyl, dialkoxyalkyl, (1-alkoxy-1-alkylthio)alkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkyl substituted with a dialkylsulfonium salt, cyanoalkyl, carbamoylalkyl, carbalkoxyalkyl, carbalkoxyalkenyl, formylalkyl, dialkylaminoalkenyl, saturated and unsaturated heterocyclic radicals selected from the group consisting of furyl, pyridyl, thienyl, thiiranyl, oxiranyl, and aziridinyl wherein the radical is joined to the pyridine ring by a C--C bond, and lower alkyl substituted with a saturated or unsaturated heterocyclic radical selected from the group consisting of furyl, pyridyl, thienyl, thiiranyl, oxiranyl, and aziridinyl;
- R.sub.1 and R.sub.2 are independently selected from alkyl, fluorinated methyl, and chlorofluorinated methyl radicals, provided that one of R.sub.1 and R.sub.2 must be a fluorinated methyl or chlorofluorinated methyl radical;
- X is ##STR49## where R.sub.3 is as defined below;
- and Y is selected from the group consisting of ##STR50## wherein Z.sub.1 is selected from O and NR.sub.7 where R.sub.7 is selected from hydrogen and lower alkyl and wherein Z.sub.2 is selected from O and S, and wherein R.sub.3 in each occurrence is independently selected from hydrogen, alkyl C.sub.1-4, alkenylalkyl C.sub.3-4, haloalkyl C.sub.1-4, cyanoalkyl, cycloalkanylalkyl, alkynylalkyl C.sub.3-4, provided that when Z.sub.2 is S, R.sub.3 must be lower alkyl C.sub.1-2 ;
- ##STR51## wherein R.sub.4 is selected from hydrogen and halogen;
- ##STR52## wherein R.sub.5 and R.sub.6 are independently selected from hydrogen, lower alkyl, and phenyl;
- --CH.sub.2 OH;
- and
- --C.tbd.N.
6 more elements
A herbicidal composition containing a herbicidally effective amount of a compound represented by the structural formula ##STR59## wherein:
- R is selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, lower alkenylalkyl, haloalkyl, haloalkenyl, C.sub.3-7 cycloalkyl, C.sub.3-6 cycloalkanylalkyl, phenyl, alkoxyalkyl, benzyloxymethyl, alkylthioalkyl, dialkoxyalkyl, (1-alkoxy-1-alkylthio)alkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkyl substituted with a dialkylsulfonium salt, cyanoalkyl, carbalkoxyalkyl, carbalkoxyalkenyl, dialkylaminoalkenyl, saturated and unsaturated heterocyclic radicals selected from the group consisting of furyl, pyridyl, thienyl, thiiranyl, oxiranyl, and aziridinyl wherein the radical is joined to the pyridine ring by a C--C bond, and lower alkyl substituted with a saturated or unsaturated heterocyclic radical selected from the group consisting of furyl, pyridyl, thienyl, thiiranyl, oxiranyl, and aziridinyl;
- R.sub.1 and R.sub.2 are independently selected from alkyl, fluorinated methyl, and chlorofluorinated methyl radicals, provided that one of R.sub.1 and R.sub.2 must be a fluorinated methyl or chlorofluorinated methyl radical;
- and
- X is ##STR60## where R.sub.3 is as defined below;
- and Y is selected from the group consisting of ##STR61## wherein Z.sub.1 is selected from O and NR.sub.7 where R.sub.7 is selected from hydrogen and lower alkyl and wherein Z.sub.2 is selected from O and S, and wherein R.sub.3 in each occurrence is independently selected from hydrogen, alkyl C.sub.1-4, alkenylalkyl C.sub.3-4, haloalkyl C.sub.2-4, cyanoalkyl, cycloalkanylalkyl, alkynylalkyl C.sub.3-4, provided that when Z.sub.2 is S, R.sub.3 must be lower alkyl C.sub.1-2 ;
- ##STR62## wherein R.sub.4 is selected from hydrogen and halogen;
- ##STR63## wherein R.sub.5 and R.sub.6 are independently selected from hydrogen, lower alkyl, and phenyl;
- --CH.sub.2 OH;
- and
- --C.tbd.N.
7 more elements
A herbicidal method comprising applying to the plant locus an effective amount of a compound represented by the structural formula ##STR69## wherein:
- R is selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, lower alkenylalkyl, haloalkyl, haloalkenyl, C.sub.3-7 cycloalkyl, C.sub.3-6 cycloalkanylalkyl, phenyl, alkoxyalkyl, benzyloxymethyl, alkylthioalkyl, dialkoxyalkyl, (1-alkoxy-1-alkylthio)alkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkyl substituted with a dialkylsulfonium salt, cyanoalkyl, carbalkoxyalkyl, carbalkoxyalkenyl, dialkylaminoalkenyl, saturated and unsaturated heterocyclic radicals selected from the group consisting of furyl, pyridyl, thienyl, thiiranyl, oxiranyl, and aziridinyl wherein the radical is joined to the pyridine ring by a C--C bond, and lower alkyl substituted with a saturated or unsaturated heterocyclic radical selected from the group consisting of furyl, pyridyl, thienyl, thiiranyl, oxiranyl, and aziridinyl;
- R.sub.1 and R.sub.2 are independently selected from alkyl, fluorinated methyl, and chlorofluorinated methyl radicals, provided that one of R.sub.1 and R.sub.2 must be a fluorinated methyl or chlorofluorinated methyl radical;
- and
- X is ##STR70## where R.sub.3 is as defined below;
- and Y is selected from the group consisting of ##STR71## wherein Z.sub.1 is selected from O and NR.sub.7 where R.sub.7 is selected from hydrogen and lower alkyl and wherein Z.sub.2 is selected from O and S, and wherein R.sub.3 in each occurrence is independently selected from hydrogen, alkyl C.sub.1-4, alkenylalkyl C.sub.3-4, haloalkyl C.sub.2-4, cyanoalkyl, cycloalkanylalkyl, alkynylalkyl C.sub.3-4, provided that when Z.sub.2 is S, R.sub.3 must be lower alkyl C.sub.1-2 ;
- ##STR72## wherein R.sub.4 is selected from hydrogen and halogen;
- ##STR73## wherein R.sub.5 and R.sub.6 are independently selected from hydrogen, lower alkyl, and phenyl;
- --CH.sub.2 OH;
- and
- --C.tbd.N.
7 more elements
Dependencies are inferred from the claim text.